WO2006115301A1

WO2006115301A1 - Organic electroluminescent device

Info

Publication number: WO2006115301A1
Application number: PCT/JP2006/309142
Authority: WO
Inventors: Takeshi Murakami; Kazunari Yagi; Seiji Ichijima; Tatsuya Igarashi; Tasuku Satou
Original assignee: Fujifilm Corporation
Priority date: 2005-04-25
Filing date: 2006-04-25
Publication date: 2006-11-02
Also published as: TWI418606B; TW200702423A; EP1874894B1; EP1874894A1; US20090079329A1; US8048538B2

Abstract

An organic electroluminescent device comprising: a pair of electrodes; and at least one organic layer between the pair of electrodes, wherein the at least one organic layer contains a specific compound in which a transition metal and a carbene carbon are bonded to each other.

Description

006/309142

DESCRIPTION

ORGANIC ELECTROLUMINESCENT DEVICE

Technical Field

The present invention relates to an organic electroluminescent device which can emit light by converting electric energy into optical energy.

Background Art

Since an organic electroluminescent device (organic EL device) can emit high-brightness light with a low voltage, the organic EL device has been actively studied. In general, the organic EL device includes an organic layer (hereinafter, also referred to as an organic compound layer) having a light emitting layer and a pair of electrodes with the organic layer therebetween and uses light emitted from exciters generated by recombining electrons injected from a negative electrode and holes injected from a positive electrode with each other in the light emitting layer.

In recent years, increase in efficiency of the organic EL device has been advanced by using a phosphorescent material. An iridium complex (WO 00/57676) and a platinum complex are known as the phosphorescent material, but the phosphorescent material requires improvement in efficiency, durability, and emitted color.

Disclosure of the Invention

An object of 1he present invention is to provide an organic electroluminescent device which can emit a variety of color light with high durability or high light emitting efficiency.

The object is accomplished by the following means.

(1) An organic electroluminescent device comprising: a pair of electrodes; and at least one organic layer between the pair of electrodes, wherein the at least one organic layer contains a compound represented by Formula (1):

wherein M represents a transition metal atom or a transition metal ion; R¹¹ and R¹² each independently represents a hydrogen atom or a substituent group, and R¹¹ and R¹² may be independently bonded to M or R¹¹ and R¹² may be bonded to each other to form a cyclic structure;

L^π represents a ligand, and L^π may be bonded to at least one of R^π and R¹²;

X¹¹ represents a counter ion; n¹¹ represents an integer of 0 to 5; n¹² represents an integer of 1 to 6; n¹³ represents an integer of 0 to 3; and

C represents a carbene carbon, which is bonded to R¹¹ and R¹² to coordinate with M.

(2) The organic electroluminescent device as described in (1) above, wherein the compound represented by Formula (1) is a compound represented by Formula

(2):

Formula ( 2)

wherein M represents a transition metal atom or a transition metal ion;

R²¹, R²², R²³ and R²⁴ each independently represents a hydrogen atom or a substituent group, and R²¹, R²², R²³ and R²⁴ may be independently bonded to M or R²¹, R²², R²³ and R²⁴ may be bonded to each other to form a cyclic structure;

L²¹ represents a ligand, and L²¹ may be bonded to at least one of R²¹, R²², R²³ and R²⁴;

X²¹ represents a counter ion; n²¹ represents an integer of 0 to 5; n²² represents an integer of 1 to 6; n²³ represents an integer of 0 to 3; and

C represents a carbene carbon, which is bonded to two nitrogen atoms to coordinate with

M.

(3) The organic electroluminescent device as described in (2) above, wherein the compound represented by Formula (2) is a compound represented by Formula

(3):

Formula ( 3 )

wherein M represents a transition metal atom or a transition metal ion;

R³¹, R³² and R³³ each independently represents a hydrogen atom or a substituent group, and R³¹, R³² and R³³ may be bonded to each other to form a cyclic structure or R³¹, R³² and R³³ may coordinate with M through an atom of R³¹, R³² and R³³ respectively;

R³⁴ represents a substituent group, provided that when R³⁴ is plural, a plurality of R³⁴ may equal to or different from each other, and a plurality of R³⁴ may be bonded to each other to form a cyclic structure or R³⁴ may coordinate with M through an atom of R³⁴;

L³¹ represents a ligand;

X³¹ represents a counter ion; n³¹ represents an integer of 0 to 4; n³² represents an integer of 1 to 3; n³³ represents an integer of 0 to 2; m³¹ represents an integer of 0 to 4; and

C represents a carbene carbon, which is bonded to two nitrogen atoms to coordinate with M by means of two electrons of the carbene carbon.

(4) The organic electroluminescent device as described in (3) above, wherein the compound represented by Formula (3) is a compound represented by Formula (4):

Formula ( 4)

wherein R⁴¹, R⁴² and R⁴³ each independently represents a hydrogen atom or a substituent group, and R⁴¹, R⁴² and R⁴³ may be bonded to each other to form a cyclic structure or R⁴¹, R⁴² and R⁴³ may coordinate with M through an atom of R⁴¹, R⁴² and R⁴³ respectively;

R⁴⁴, R⁴⁵ and R⁴⁶ each independently represents a substituent group, provided that when R⁴⁴, R⁴⁵ and R⁴⁵ are plural respectively, a plurality of R⁴⁴, a plurality of R⁴⁵ and a plurality of R⁴⁶ may be bonded to each other to form a cyclic structure respectively or R⁴⁴, R⁴⁵ and R⁴⁵ may coordinate with M through an atom of R⁴⁴, R⁴⁵ and R⁴⁶ respectively; n⁴¹ represents an integer of 0 to 2; n⁴² represents an integer of 1 to 3; and m⁴¹, m⁴² and m⁴³ each independently represents an integer of 0 to 4.

(5) The organic electroluminescent device as described in any of (1) to (4) above, wherein a ligand containing the carbene carbon is a tridentate to hexadentate ligand.

(6) The organic electroluminescent device as described in (1) above, wherein the compound represented by Formula (1) is a compound represented by Formula

(5):

Formula ( 5 )

wherein R⁵² and R⁵³ each independently represents a hydrogen atom or a substituent group, and R⁵² and R⁵³ may be bonded to each other to form a cyclic structure;

R⁵⁴, R⁵⁵- and R⁵⁶ each independently represents a substituent group, provided that when R⁵⁴,

4 R⁵⁵ and R⁵⁶ are plural respectively, a plurality of R⁵⁴, a plurality of R⁵⁵ and a plurality of R⁵⁶ may be bonded to each other to form a cyclic structure respectively;

Y⁵¹ and Y⁵² each independently represents a single bond or a connection group; n⁵¹ represents 0 or 1; and m⁵¹, m⁵² and m⁵³ each independently represents an integer of 0 to 4.

(7) The organic electroluminescent device as described in any of (1) to (6) above, wherein the at least one organic layer includes a light emitting layer, and wherein the light emitting layer contains at least a light emitting material and a compound represented by any of Formulae (1) to (5),

(8) The organic electroluminescent device as described in any of (1) to (7) above, wherein the at least one organic layer includes a light emitting layer, and wherein at least one layer between the light emitting layer and a positive electrode contains a compound represented by any of Formulae (1) to (5).

(9) The organic electroluminescent device as described in any of (1) to (7) above, wherein the at least one organic layer includes a light emitting layer, and wherein at least one layer between the light emitting layer and a negative electrode contains a compound represented by any of Formulae (1) to (5).

In an organic electroluminescent device having at least one organic layer between a pair of electrodes, it is possible to improve the durability of a device (reduction of the driving voltage and inhibition for the generation of dark spots along with the deterioration of a device when it is driven for a long time.) or the light emitting efficiency of a device by using a compound represented by any of formulae (1) to (5) which has a bond between a transition metal and a carbene carbon in the organic layer.

Further, by employing a compound represented by any of formulae (1) to (5) in at least one organic layer laminated especially between a light emitting layer and a positive electrode or between a light emitting layer and a negative electrode, it is possible to further improve a light emitting efficiency in addition to the durability of a device (reduction of the driving voltage and inhibition for the generation of dark spots along with the deterioration of a device when it is driven for a long time.)

Best Mode For Carrying Out the Invention

Hereinafter, the present invention will be described in detail.

The present invention provides an organic electroluminescent device having at least one organic layer between a pair of electrodes. Here, the at least one organic layer contains a compound represented by formulae (1) to (5) (having the same meaning as the compound according to the present invention in which a transition metal and a carbene carbon are bonded to each other.)

Formula (1) is described. M represents a transition metal atom or a transition metal ion. R¹¹ and R¹² represent a hydrogen atom or a substituent group independently. Both or one of R¹ * and R¹² may coordinate with M through an atom(s) of both or one of R¹¹ and R¹². L¹¹ represents a ligand and X¹¹ represents a counter ion. n¹¹ represents an integer of 0 to 5, n¹² represents an integer of 1 to 6, and n¹³ represents an integer of 0 to 3. C represents a carbene carbon. The carbene carbon is bonded to R¹¹ and R¹² (preferably in a covalent bond) and coordinates with M by means of two electrons of carbon.

The transition metal atom used in the present invention is not particularly limited, but is preferably one of ruthenium, rhodium, palladium, tungsten, rhenium, osmium, indium, and platinum, more preferably one of palladium, rhenium, rhodium, iridium, and platinum, and most preferably one of palladium, rhodium, iridium, and platinum.

Examples of the substituent group representd by R¹¹ and R¹² can include an alkyl group (which has preferably a carbon number of 1 to 30, more preferably a carbon number of 1 to 2O₃ and most preferably a carbon number of 1 to 10, and examples of which can include methyl, ethyl, iso- propyl, tert-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, and cyclohexyl), an alkenyl group (which has preferably a carbon number of 2 to 30, more preferably a carbon number of 2 to 20, and most preferably a carbon number of 2 to 10, and examples of which can include vinyl, aryl, 2-butenyl, and 3-pentenyl), and an alkinyl group (which has preferably a carbon number of 2 to 30, more preferably a carbon number of 2 to 20, and most preferably a carbon number of 2 to 10, and examples of which can include propargyl and 3-pentinyl).

In addition, other examples of the substituent group representd by R¹¹ and R¹² can include an aryl group (which has preferably a carbon number of 6 to 30, more preferably a carbon number of 6 to 20, and most preferably a carbon number of 6 to 12, and examples of which can include phenyl, p-methylphenyl, naphthyl, and anthranil), a substituted or non-substituted amino group (which has preferably a carbon number of 0 to 30, more preferably a carbon number of 0 to 2O₃ and most preferably a carbon number of 0 to 10, and examples of which can include amino, methyl amino, dimethyl amino, diethyl amino, dibenzyl amino, diphenyl amino, and ditolyl amino), an alkoxy group (which has preferably a carbon number of 1 to 30, more preferably a carbon number of 1 to 20, and most preferably a carbon number of 1 to 10, and examples of which can include methoxy, ethoxy, butoxy, and 2-ethylhexyloxy), an aryloxy group (which has preferably a carbon number of 6 to 30, more preferably a carbon number of 6 to 20, and most preferably a carbon number of 6 to 12, and examples of which can include phenyloxy, 1-naphtayloxy, and 2- naphthyloxy), and a heterocyclic oxy group (which has preferably a carbon number of 1 to 30, more preferably a carbon number of 1 to 20, and most preferably a carbon number of 1 to 12, and examples of which can include pyridyloxy, pyrazyloxy, pyrimidyloxy, and quinolyloxy). In addition, other examples of the substituent group representd by R¹¹ and R¹² can include an acyl group (which has preferably a carbon number of 1 to 30, more preferably a carbon number of 1 to 20, and most preferably a carbon number of 1 to 12, and examples of which can inclu.de acetyl, benzoyl, formyl, and pivaloyl), an alkoxycarbonyl group (which has preferably a carbon number of 2 to 30, more preferably a carbon number of 2 to 20, and most preferably a carbon number of 2 to 12, and examples of which can include methoxycarbonyl and ethoxycarbonyl), an aryloxycarbonyl group (which has preferably a carbon number of 7 to 30, more preferably a carbon number of 7 to 20, and most preferably a carbon number of 7 to 12, and examples of which can include phenyloxycarbonyl), an acyloxy group (which has preferably a carbon number of 2 to 30, more preferably a carbon number of 2 to 20, and most preferably a carbon number of 2 to IO . and examples of which can include acetoxy and benzoyloxy), and an acyl amino group (which ha.s preferably a carbon number of 2 to 30, more preferably a carbon number of 2 to 20, and most preferably a carbon number of 2 to 10, and examples of which can include acetyl amino and benzoyl amino).

In addition, other examples of the substituent group representd by R¹¹ and R¹² can include an alkoxycarbonyl amino group (which has preferably a carbon number of 2 to 30, more preferably a carbon number of 2 to 20, and most preferably a carbon number of 2 to 12, and examples of which can include methoxycarbonyl amino), an aryloxycarbonyl amino group (which has preferably a carbon number of 7 to 30, more preferably a carbon number of 7 to 20, and most preferably a carbon number of 7 to 12, and examples of which can include phenyloxycarbonyl amino), a sulfonyl amino group (which has preferably a carbon number of 1 to 3O₅ more preferably a carbon number of 1 to 20, and most preferably a carbon number of 1 to 12, and examples of which can include methane sulfonyl amino and benzene sulfonyl amino), and a sulfamoyl group (which has preferably a carbon number of 0 to 30, more preferably a carbon number of 0 to 20, and most preferably a carbon number of 0 to 12, and examples of which can include sulfamoyl, methylsulfamoyl, dimethylsulfamoyl, and phenylsulfamoyl).

In addition, other examples of the substituent group representd by R^π and R¹² can include a carbamoyl group (which has preferably a carbon number of 1 to 30, more preferably a carbon number of 1 to 20, and most preferably a carbon number of 1 to 12, and examples of which can include carbamoyl, methylcarbamoyl, diethylcarbamoyl, and phenylcarbamoyl), an alkylthio group (which has preferably a carbon number of 1 to 30, more preferably a carbon number of 1 to 120, and most preferably a carbon number of 1 to 12, and examples of which can include methylthio and ethylthio), an arylthio group (which has preferably a carbon number of 6 to 30, more preferably a carbon number of 6 to 20, and most preferably a carbon number of 6 to 12, and examples off which can include phenylthio), and a heterocyclic thio group (which has preferably a carbon number of 1 to 30, more preferably a carbon number of 1 to 20, and most preferably a carbon number of 1 to 12, and examples of which can include pyridylthio, 2-benzimizolylthio, 2-benzoxazolylthio, and 2- benzthiazolylthio) .

In addition, other examples of the substituent group representd by Rⁿ and R¹² can include a sulfonyl group (which has preferably a carbon number of 1 to 30, more preferably a carbon number of 1 to 20, and most preferably a carbon number of 1 to 12, and examples of which can include mesyl and tosyl), a sulfinyl group (which has preferably a carbon number of 1 to 30, more preferably a carbon number of 1 to 20, and most preferably a carbon number of 1 to 12, and examples of which can include methane sulfinyl and benzene sulfinyl), an ureido group (which has preferably a carbon number of 1 to 30, more preferably a carbon number of 1 to 20, and most preferably a carbon number of 1 to 12, and examples of which can include ureido, methylureido, and phenylureido), an amide phosphate group (which has preferably a carbon number of 1 to 30, more preferably a carbon number of 1 to 20, and most preferably a carbon number of 1 to 12, and examples of which can include diethyl amide phosphate and phenyl amide phosphate), an hydroxy group, a mercapto group, and a halogen atom (examples of which can include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom).

In addition, other examples of the substituent group representd by R¹¹ and R¹² can include a cyano group, a sulfo group, a carboxyl group, a nitro group, a hydroxamic acid group, a sulfino group, a hydrazino group, an imino group, a heterocyclic group (which has preferably a carbon number of 1 to 30 and more preferably a carbon number of 1 to 12 and which includes, for example, a nitrogen atom, an oxygen atom, and a sulfur atom as the hetero atom, examples of which can include imidazolyl, pyridyl, quinolyl, furyl, thienyl, piperidyl, morpholino, benzoxazolyl, benzimidazolyl, benzthiazolyl, carbazolyl, and azepinyl), a silyl group (which has preferably a carbon number of 3 to 40, more preferably a carbon number of 3 to 30, and most preferably a carbon number of 3 to 24, and examples of which can include trimethylsilyl and triphenylsilyl), and a silyloxy group (which has preferably a carbon number of 3 to 40, more preferably a carbon number of 3 to 30, and most preferably a carbon number of 3 to 24, and examples of which can include methylsilyloxy and triphenylsilyloxy). These substituent groups may be substituted again.

R¹¹ and R¹² may form a cyclic structure by bonding. R¹¹ and R¹² may coordinate with M through an atom of R¹¹ and R¹². At least one of R¹¹ and R¹² may be bonded to L¹¹ to form a chelate ligand. R¹¹ and R¹² are preferably one of an alkoxy group, an aryloxy group, a hetero aryloxy group, and a substituted amino group and more preferably one of an alkoxy group and a substituted amino group.

L^π represents a ligand. Examples of the ligand can include ligands described in "Photochemistry and Photophysics of Coordination Compounds" published in 1987 by Springer- Verlag Co. and written by H. Yersin, and "Organic Metal Chemistry - Fundamentals and Applications" published in 1982 by Shokabou Co. and written by Yamamoto Akio. The ligand is preferably one of a halogen ligand (examples of which can include a chlorine ligand and a fluorine ligand), a nitrogen-containing heterocyclic ligand (examples of which can include bipyridyl, phenanthroline, phenylpyridine, pyrazolylpyridine, benzimidazolylpyridine, phenylpyrazole, picohnate, and dipicolinate), a diketone ligand, a nitrile ligand, a CO ligand, an isonitrile ligand, a phosphorous ligand (examples of which can include phophine derivatives, phosphorous ester derivatives, and phosphinine derivatives), and a carbonic acid ligand (examples of which can include an acetic acid ligand), and more preferably a nitrogen-containing heterocyclic ligand (examples of which can include bipyridyl, phenanthroline, phenylpyridine, pyrazolylpyridine, benzimidazolylpyridine, and phenylpyrazole).

A nitrogen-containing heterocycle in the nitrogen-containing heterocyclic ligand is preferably one of a pyridine cycle, a pyrazine cycle, a pyrimidine cycle, a pyridazine cycle, a pyrrole cycle, a pyrazole cycle, an imidazole cycle, a triazole cycle, a thiazole cycle, an oxazole cycle, an oxadiazole cycle, a thiadiazole cycle, an azaphosphinine cycle and is more preferably one of a pyridine cycle, a pyrazole cycle, and an imidazole cycle.

The nitrogen-containing heterocyclic ligand may have a substituent group. Examples of the substituent group can include the groups described in relation to R¹¹, and an alkyl group, an aryl group, an alkoxy group, a fluorine atom, a cyano group, and a substituted amino group are preferable.

X¹¹ represents a counter ion. The counter ion is not particularly limited, but is preferably one of an alkali metal ion, an alkali earth metal ion, a halogen ion, a perchlorate ion, a PF₆ ion, an ammonium ion (for example, a tetramethyl ammonium ion), a borate ion, and a phosphonium ion, and more preferably one of a perchlorate ion and a PF₆ ion. n¹¹ represents an integer of 0 to 5, preferably an integer of 1 to 4, and more preferably an integer of 1 or 2. When n¹¹ is plural, a plurality of L¹¹ may be equal to or different from each other, n¹² represents an integer of 1 to 6, preferably an integer of 1 to 4, and more preferably an. integer of 1 to 3. When n¹² is plural, a plurality of carbene ligands represented by R^{1 X}-C-R¹² ma.y be equal to or different from each other, n¹³ represents an integer of 0 to 3, preferably 0 or 1, and more preferably 0. When n¹³ is plural, a plurality of X¹¹ may be equal to or different from each other.

Formula (2) is described. M, L²¹, X²¹, n²¹, n²², and n²³ are the same as M, L¹¹, X¹¹, n", n¹², and n¹³ of Formula (1) described above and preferable ranges thereof are also the same. R²¹, R²². R²³, and R²⁴ represent a hydrogen atom or a substituent group and examples of the substituent group can include the groups described with reference to R¹¹. R²¹, R²², R²³, and R²⁴ may form a. ring structure, respectively, by bonding. R²¹, R²², R²³, and R²⁴ may coordinate with M through an atom of R²¹, R²²; R²³, and R²⁴, respectively. R²¹, R²², R²³, and R²⁴ may be bonded to L²¹ to form, a chelate ligand, respectively. R²¹, R²², R²³, and R²⁴ are preferably one of an alkyl group, an aryl group, a heteroaryl group, an alkenyl group, an alkoxy group, an aryloxy group, an alkyl amino group, an aryl amino group, and a heterocyclic amino group, more preferably one of an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, and an aryloxy group, and most preferably one of an alkyl group, an aryl group, and a heteroaryl group.

A carbene ligand formed out of a carbene carbon, two nitrogen atoms, R²¹, R²², R²³, and R²⁴ has preferably a ring-shaped structure containing the carbene carbon and the two nitrogen atoms, more preferably a 5-membered or 6-membered ring structure, and most preferably a 5- membered ring structure represented by Formula (Z-I).

Formula ( Z - 1 )

In the above-mentioned formula, R⁶¹, R⁶², R⁶³, and R⁶⁴ represent a hydrogen atom or a substituent group. C represents a carbene carbon. The carbene carbon is boned to two nitrogen atoms and has two electrons, which can coordinate with a transition metal, on the carbon.

Formula (Z-I) is described. R⁶¹, R⁶², R⁶³, and R⁶⁴ are the same as M, R²², R²³, L²¹, and X²¹ of Formula (2) described above and preferable ranges thereof are also the same.

Formula (3) is described. M, R³¹, R³², R³³, L³¹, and X³¹ are the same as M, R²¹, R²², R²³, L²¹, and X²¹ of Formula (2) described above and preferable ranges thereof are also the same, respectively. R³⁴ represents a substituent group and examples of the substituent group can include the groups described with reference to R¹¹. A plurality of R³⁴ may equal to or different from each other. The plurality of R³⁴ may form a ring structure, respectively, by bonding or the atom on R³⁴ may coordinate with M. R³⁴ is preferably one of an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, a fluorine atom, a cyano group, and a substituted amino group, more preferably one of an alkyl group, an aryl group, a fluorine atom, and a cyano group, and most preferably one of a fluorine atom and a cyano group, n³¹ represents an integer of 0 to 4 and preferably an integer of 1 to 4. n³² represents an integer of 1 to 3 and preferably 1 or 2. n³³ represents an integer of 0 to 2 and preferably 0 or 1. m³¹ represents an integer of 0 to 4 and preferably an integer of 0 to 2. When m³¹ is plural, a plurality of R³⁴ may be equal to or different from each other.

Formula (4) is described. R⁴¹, R⁴², R⁴³, R⁴⁴, n⁴², and m⁴¹ are the same as R³¹, R³², R³³, R³⁴, n³², and m³¹ of Formula (3) described above and preferable ranges thereof are also the same, respectively. R⁴⁵ and R⁴⁵ represent a substituent group and examples of the substituent group can include the groups described with reference to R¹¹. When m⁴² is plural, a plurality of R⁴⁵ may be equal to or different from each other. A plurality of R⁴⁵ may form a ring structure, respectively', by bonding or the atom on R⁴⁵ may coordinate with an iridium atom. R⁴⁵ is preferably one of an aJkyl group, an aryl group, a heteroaryl group, an alkoxy group, a fluorine atom, a cyano group, and a substituted amino group, more preferably one of an alkyl group, an aryl group, an alkoxy groujp, and a substituted amino group, and most preferably one of an alkoxy group and a substituted amino group, n⁴² represents an integer of 0 to 4 and preferably an integer of 0 to 2. When m⁴³ is plural, a plurality of R⁴⁶ may be equal to or different from each other. A plurality of R⁴⁶ may form a ring structure, respectively, by bonding or the atom on R⁴⁵ may coordinate with an iridium atom. RJ⁴⁶ is preferably one of an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, a fluorine atom, a cyano group, and a substituted amino group, more preferably one of an alkyl group, atx aryl group, a fluorine atom, and a cyano group, and most preferably one of a fluorine atom and a cyano group, m⁴³ represents an integer of 0 to 4 and preferably an integer of 0 to 2. n⁴¹ represents an. integer of 0 to 2 and preferably 1 or 2.

In the compounds represented by Formulas (1) to (4), the ligand including a carbene carbon is preferably tridentate to hexadentate and more preferably tridentate or quadridentate.

Formula (5) is described. R⁵² and R⁵³ represent a hydrogen atom or a substituent grou/p and examples of the substituent group can include the groups described with reference to R¹¹. R⁵² and R^S3 may form a ring structure, respectively, by bonding, are preferably one of an alkyl group, an aryl group, a heteroaryl group, an alkenyl group, an alkoxy group, an aryloxy group, an alkyl amino group, an aryl amino group, and a heterocyclic amino group, more preferably one of an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, and an aryloxy group, and most preferably one of an alkyl group, an aryl group, and a heteroaryl group.

A carbene ligand formed out of a carbene carbon, two nitrogen atoms, and R⁵² and R⁵³ has preferably a ring-shaped structure containing the carbene carbon and the two nitrogen atoms, more preferably a 5-membered or 6-membered ring structure, and most preferably a 5-membered rirLg structure represented by Formula (Z-2).

Formula ( Z - 2 )

In the above-mentioned formula, R⁹², and R⁹³ represent a hydrogen atom or a substituent group and R⁹⁴, R⁹⁵, and R⁹⁶ represent a substituent group. Y⁹¹ and Y⁹² represent a single bond or a connection group, n⁹¹ represent 0 or 1 and m⁹¹, m⁹², and m⁹³ represent an integer of 0 to 4. C represents a carbene carbon. The carbene carbon is boned to two nitrogen atoms and has two electrons, which can coordinate with a transition metal, on the carbon.

R⁵⁴ and R⁵⁶ represent a substituent group and examples of the substituent group can include the groups described with reference to R¹¹. When m⁵¹ and m⁵³ are plural, a plurality of R⁵⁴ and R⁵⁶ may be equal to or different from each other and may form a ring structure, respectively, by bonding. R⁵⁴ and R⁵⁶ are preferably one of an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, a fluorine atom, a cyano group, and a substituted amino group, more preferably one of an alkyl group, an aryl group, a fluorine atom, and a substituted amino group, and most preferably one of a fluorine atom and a substituted amino group, m⁵¹ and m⁵³² represent an integer of 0 to 4 and preferably an integer of 0 to 2.

R⁵⁵ represents a substituent group and examples of the substituent group can include the groups described with reference to R¹¹. A plurality of R⁵⁵ may be equal to or different from each other, or may form a ring structure, respectively, by bonding. R⁵⁵ is preferably one of an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, a fluorine atom, a cyano group, and a substituted amino group, more preferably one of an alkyl group, an aryl group, an alkoxy group, and a substituted amino group, and most preferably one of an alkoxy group and a substituted amino group. m^S2 represents an integer of 0 to 4 and preferably an integer of 0 to 2. Y⁵¹ and Y⁵² represent a single bond or a connection group. The connection group is not particularly limited, but is preferably a connection group having one of a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom, and a silicon atom. Specific examples thereof are described below but the connection group is not limited.

CH₃ Ph

Λ ^^N\

The connection groups may be substituted again and examples of the substituent group can include the substituent groups described with reference to R^π in Formula (1). The substituent group is preferably one of an alkyl group, an aryl group, a heteroaryl group, an alkenyl group, an alkoxy group, an aryloxy group, an alkyl amino group, an aryl amino group, and a heterocyclic amino group, more preferably one of an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, and an aryloxy group, and most preferably one of an alkyl group, an aryl group, and a heteroaryl group. Y⁵¹ and Y⁵² are preferably one of a single bond, an alkyl group, an aryl group, and a silyl group, and more preferably one of a single bond, a dimethyl methylene group, and an ethylene group, n⁵¹ represents O or 1 and preferably O.

Formula (Z-2) is described. R⁹², R⁹³, R⁹⁴, R⁹⁵, R⁹⁶, Y⁹¹, Y⁹², m⁹¹, m⁹², m⁹³, and n⁹¹ are the same as R⁵², R⁵³, R⁵⁴, R⁵⁵, R⁵⁶, Y⁵¹, Y⁵², m⁵¹, m⁵², m⁵³, and n⁵¹ of Formula (5) described above and preferable ranges thereof are also the same.

The compounds represented by Formulas (1) to (5) may be low-molecular compounds. The oligomer compounds and the polymer compounds (of which the weight-average molecular weight (in polystyrene equivalent)) are preferably in the range of 1,000 to 5,000,000, more preferably in the range of 2,000 to 1,000,000, and most preferably in the range of 3,000 to 100,000). In case of the polymer compounds, the structures represented by Formulas (1) to (5) may be included in the main chain of a polymer or in the side chain of the polymer. The polymer compounds may be a homo-polymer compound or a copolymer. The compounds according to the present invention is preferably is a low-molecular compound.

Examples of the compounds according to the present invention are described below, but the present invention is not limited to the examples.

Compound ( i ) Compound (5)

Compound (2)

Compound (7)

Compound (3)

Compound (4)

Compound (9) Compound (13)

Compound (10) Compound (14)

Compound ( i 1 ) Compound (15)

Compound (i 7) Compound (21)

Compound (18)

Compound (22)

Compound (23)

Compound (2 O)

Compound (2 5)

Compound (31 )

Compound (2 6)

Compound (32)

Compound (2 7 )

Compound (2 8)

Compound (33)

Compound (29)

Compound (34) Compound (36)

Compound (35) Compound (37)

Compound (38) Compound (42)

Compound (39) Compound (43)

Compound (40⁾

Compound (44)

Compound (41 )

C

Compound (46)

Compound (50) 4)

Compound (47⁾ compound (51)

Compound (55)

Compound (48)

Compound (52) Compound (56)

Compound (49) Compound (53⁾

57)

Compound (58) (ClO₄)

Compound (62)

Compound (66)

Compound ⁽61⁾ Compound (65)

Compound (68) (ClO₄)

Compound (72)

Compound (76)

Compound (70)

Compound (74)

Compound (71) Compound (75)

Compound (78) (ClO₄)

Compound (82)

Compound C 86)

Compound (80) Compound (84)

Compound (81) Compound (85)

Compound ⁽8⁸⁾ compound (₉3)

Compound (98)

Compound (89⁾ Compound (94)

Compound (99)

Compound (9O) Compound (95)

Compound (91) Compound ⁽96⁾

Compound (92) Compound (97)

Compound (100) Compound (104)

Compound ( 1 O 1 ) Compound (105)

Compound (102) Compound (106)

Compound (103) Compound ( 107)

Compound (118)

Compound (108) Compound (113)

Compound ₍109₎ Compound (114⁾ Compound ⁽119⁾

Compound (110) Compound ⁽115⁾ compound (120)

Compound Oil) Compound ⁽116⁾ Compound (121)

C

Compound ⁽122⁾

Compound (123) Compound (128)

Compound (124) Com ound (129)

Compound (130)

Compound (131)

Compound (127)

ompound (137) Compound (141 )

compound (138)

Compound (142)

Compound (143)

Compound (144)

Compound (145)

Compound (150) Compound (155)

Com

pound 046) Compound (156)

Compound (151)

Co

mpound (147) Compound (157)

Compound (152)

Compound (148) Compound (158)

Compound (149)

Compound (159) C

Compound (161)

Compound 071)

Compoun (162) Compound ⁽167⁾

Compoun

_Compound ₍1₆₃₎ Compound ⁽168⁾ J J Compound (173)

C

Compound (179)

Compound (184) _Compound (188) Compound ⁽192⁾

Compound (185) Compound (189) Compound (193)

_Compound (186) Compound (190) Compound ⁽194⁾

Compound ⁽187⁾ Compound (191) _Compound (195)

Compound (196) Compound (200) Compound ⁽204⁾

Compound (197) Compound (201) Compound (205)

Compound (199) Compound ⁽203⁾ _{Compound (207)}

Compound (208) Compound (212) Compound (216)

Compound (209) Compound (213) Compound (217)

Compound (210) Compound (214) Compound (218)

Compound (211) Compound (215) Compound (219)

Compound (220) Compound (224) Compound ⁽228⁾

Compound (221) . Compound (225) Compound ⁽229⁾

Compound (222) Compound (226) Compound ⁽230⁾

Compound (223) Compound (227) Compound ⁽231⁾

Compound (232) Compound (236) Compound (240)

Compound (233) Compound (237) Compound (241)

Compound (234) Compound (238) Compound (242)

Compound (235) Compound (239) Compound (243)

Compound (244)

Compound (245) Compound (249) Compound (253)

Compound (246) Compound (250)

Compound (254)

Compound (247) Compound (251)

Compound (255)

Compound (256) Compound (260) Compound (264)

Compound (257) Compound (261) Compound (265)

Compound (258) Compound (262) Compound (266)

Compound (258) Compound (263) Compound (267)

Compound (268)

Compound (272) Compound (276)

Compound (271) Compound (275)

Compound (279)

The compounds according to the present invention represented by Formulas (L) to (5) can be synthesized by the use of a variety of methods. For example, by mixing a ligand or the dissociated material with a transition metal compound at a room temperature or while .heating them, the compounds can be obtained. In case of heating, a method of over-heating the materials with micro waves is effective in addition a typical heating method. Solvent (such as halogen solvent, alcohol solvent, ether solvent, and water) or base (which may be inorganic base or organic base, examples of which can include sodium methoxy, potassium t-butoxy, triethyl amine, and potassium carbonate) may be used as needed.

For example, the synthesis of Compound (1) can be performed by the use of the following method. That is, chlorine-bridged indium complex A-I can be synthesized by the use of the method described Document 1 (J. Am. Chem. Soc. 1984, 106, 6647) or the like. Then, by nnaking a complex from complex A-I and imidazolium salt A-2 which is a precursor of a carbene ligand by the use of the reaction condition described in Document 2 (Inorg. Chem. 2004, 43, 6896) or "the like, Compound (1) can be synthesized.

A - 1 Compound ( 1 >

The synthesis of Compound (113) which is a quadridentate platinum complex can be performed by the use of the following method. That is, imidazolium salt A-3 which is a precursor of a quadridentate carbene ligand can be synthesized by the use of the method described in Document 3 (Tetrahedron, 2004, 60, 5807). Then, by making a complex from imidazolium salt A- 3 and platinum salt by the use of the reaction condition described in Document 4 (Coordination Chemistry Reviews, 2004, 248, 2247) or the like, Compound (113) can be synthesized.

A-3 Compound (113)

The compounds according to the present invention can be also synthesized by the use of the method described in Document (Angew. Chem. Lit. Ed. 2002, 41, 1290), Document 5 (".Metal Complex Chemistry," published in 1990 by Hirokawa Shoten and coauthored by Ogino Hiroshi, Matsubayasi Genetsu, and Yamamoto Yosihisa), and the like.

The compounds according to the present invention can be used as any one of a hole injecting material, a hole transporting material, a light emitting material, an electron injecting material, an electron transporting material, a hole blocking material, an electron blocking material, an exciter blocking material and a hole injection promoting material. The compounds can be used preferably as a hole injecting material, a hole transporting material, an electron blocking material, and a light emitting material, more preferably as a hole injecting material and a light emitting material, and most preferably as a light emitting material. When the compounds are used as the light emitting material, the emission of light may be any one of emission of ultraviolet rays, emission of visible rays, and emission of infrared rays, or may be any one of emission of fluorescent light and emission of phosphorescent light. The emission of phosphorescent light is most preferable.

The maximum wavelength of phosphorescent light of the compounds according to the present invention is preferably in the range of 380nm to 490nm, more preferably in the range of 400nm to 480nm, still more preferable in the range of 410nm to 470nm, and most preferably in the range of 420nm to 460nm.

The phosphorescent quantum yield of the compounds according to the present invention is preferably 20% or more, more preferably 40% or more, and most preferably 60% or more. The phosphorescent quantum yield of the phosphorescent material can be measured at 20⁰C by freezing and degassing a solution containing the phosphorescent material (for examples, a toluene solution of Ixl0^"5 mol/1).

In the organic electroluminescent device according to the present invention, the external quantum efficiency (= (the number of input electrons) / (the number of output photons) x 100 (%)) is preferably 5% or more, more preferably 10% or more, and most preferably 13% or more. As the value of the external quantum efficiency, the maximum value of the external quantum efficiency when the device is driven at 20⁰C may be used or the value of the external quantum efiBciency when the device is driven in the range of 100 to 300 cd/m² at 20⁰C may be used.

In the organic electroluminescent device according to the present invention, the internal quantum efficiency (= (external quantum efficiency) x (light extraction efficiency) / IOO (%)) is preferably 30% or more, more preferably 50% or more, and most preferably 70% or more. The light extraction efficiency of a conventional organic EL device is about 20%, but the light extraction efficiency may be set to 20% or more by devising the shape of a substrate, the shape of an electrode, the thickness of an organic layer, the thickness of an inorganic layer, the refractive index of an organic layer, the refractive index of an inorganic layer, and the like.

The organic electroluminescent device according to the present invention has at least one organic layer between a pair of electrodes of a positive electrode and a negative electrode and the organic layer is a light emitting layer or a plurality of organic layers including the light emitting layer. The organic layer may include a hole injecting layer, a hole transporting layer, an electron transporting layer, an electron transporting layer, a hole injection promoting material and a protective layer, in addition to the light emitting layer. The respective layers may have different functions. A variety of materials may be used to form the respective layers.

Structural examples of the organic layer can include a single-layered structure (light emitting layer), a two-layered structure (light emitting layer and electron transporting layer, and hole transporting layer), a three-layered structure (electron transporting layer, light emitting layer, and hole transporting layer), a four-layered structure (electron injecting layer, light emitting layer, hole transporting layer, and hole injecting layer), and a five-layered structure (electron injecting layer, electron transporting layer, light emitting layer, hole transporting layer, and hole injecting layer).

The organic electroluminescent device according to the present invention has preferably at least three layers of the hole transporting layer, the light emitting layer, and the electron transporting layer. It is preferable that the light emitting layer includes at least two kinds of a host material and a fluorescent material.

The organic electroluminescent device according to the present invention contains a compound according to the present invention preferably in at least one layer of a light emitting layer, a layer between a light emitting layer and a negative electrode and a layer between a light emitting layer and a positive electrode, more preferably in at least one layer of a light emitting layer and a layer between a light emitting layer and a positive electrode, still more preferably in a light emitting layer.

When a compound according to the present invention is used in a light emitting layer, the light emitting layer preferably contains at least a compound according to the present invention and a light emitting material.

In a light emitting layer, a compound according to the present invention is preferably contained in 0.1 mass% to 99.5 mass%, more preferably 1 mass% to 98 mass%, particularly more preferably 5 mass% to 90 mass%.

Further, when a compound according to the present invention is contained in a layer between a light emitting layer and a negative electrode or a layer between a light emitting layer and. a positive electrode, a compound according to the present invention is preferably contained in 10 mass% to 100 mass%, more preferably 30 mass% to 100 mass%, particularly more preferably 50 mass% to 100 mass%.

The light emitting material contained in the light emitting layer is not particularly limited and can be properly selected from the known materials. Examples of the fluorescent material can include materials described in Paragraph No. 0027 of Japanese Unexamined Patent Application Publication No. 2004-146067 and materials described in Paragraph No. 0057 of Japanese Unexamined Patent Application Publication No. 2004-103577. Examples of the phosphorescent material can include heavy metal (such as indium, platinum, rhenium, osmium, copper, and gold) complexes, and contains preferably the indium complex or the platinum complex. Specific examples thereof can include those described in Paragraph Nos. 0051 to 0057 of Japanese Unexamined Patent Application Publication No. 2004- 221068. Among them, a platinum complex having a quadridentate ligand is preferable, a platinum complex having a quadridentate ligand of which a nitrogen atom coordinates is more preferable, a platinum complex having a quadridentate ligand of which a nitrogen atom of a 6-membered heterocycle coordinates is still more preferable, and a platinum complex having a quadridentate ligand of a non-cyclic structure of which a nitrogen atom of a 6-membered heterocycle coordinates is most preferable. Examples of the platinum complex having a quadridentate ligand can include a platinum complex represented by Formula (P-I) described later. Platinum complexes having these quadridentate ligands can be synthesized by a method such as a method described in WO2004-108857A1.

The compounds according to the present invention may be used as a host material of the light emitting layer. When the compounds according to the present invention are used as the host material, the light emitting material contains preferably a platinum complex having a quadridentate ligand. The platinum complex having a quadridentate ligand is preferably a platinum complex having a quadridentate ligand of which a nitrogen atom coordinates, more preferably a platinum complex having a quadridentate ligand of which a nitrogen atom of a 6- membered heterocycle coordinates, and most preferably a platinum complex having a quadridentate ligand of a non-cyclic structure of which a nitrogen atom of a 6-membered heterocycle coordinates. Examples of the platinum complex having a quadridentate ligand can include a platinum complex represented by Formula (P-I) described later.

The compounds according to the present invention may be used in an adjacent layer of a light emitting layer (where the adjacent layer means a layer adjacent to the light emitting layer, such as a hole transporting layer, the hole injecting layer, an electron transporting layer, an electric charge blocking layer, and an exciter blocking layer). Particularly, the compounds according to the present invention are contained preferably in the adjacent layer between the positive electrode and the light emitting layer and more preferably in the hole transporting layer and/or a hole injection promoting layer. The hole injecting layer means a layer adjacent to a light emitting layer and promoting hole injection into a light emitting layer.

When the compounds according to the present invention are used in the adjacent layer of a light emitting layer, the light emitting layer contains preferably at least one compound according to the present invention, at least one light emitting material and at least one host material, or at least one host material and at least one light emitting material, and more preferably at least one host material and at least one light emitting material. The light emitting material contained in the light emitting layer is preferably a phosphorescent material, more preferably a heavy metal complex, still more preferably heavy metal complexes, still more preferably an iridium complex or a platinum complex, and most preferably a platinum complex.

As a platinum complex, a platinum complex having a quadridentate ligand is preferable, the platinum complex having a quadridentate ligand of which a nitrogen atom coordinates is more preferable, the platinum complex having a quadridentate ligand of which a nitrogen atom of a 6- membered heterocycle coordinates is still more preferable, and the platinum complex having a quadridentate ligand of a non-cyclic structure of which a nitrogen atom of a 6-membered heterocycle coordinates is most preferable. Examples of the platinum complex having a quadridentate ligand can include a platinum complex represented by Formula (P-I) described later.

Examples of the host material contained in the light emitting layer can include the host material described later. The host material is preferably one of a heavy metal complex, a carbazole derivative, an aromatic three-degreed amine compound, and a thiophene derivative and has preferably a plurality of carbazole frameworks and/or aromatic three-degreed amine frameworks in a molecule.

Hereafter, Formula (P-I) is explained below.

Formula (P-I)

Here, Pt represents a platinum ion, L¹¹, L¹², L¹³, L¹⁴, and L¹⁵ represent a ligand coordinating with the platinum ion. A cyclic ligand is not formed by means of additional existence of an atom group between L¹¹ and L¹⁴.

L¹⁵ does not form a cyclic ligand by means of the coupling to both of L¹¹ and L¹⁴. Y¹¹, Y¹², and Y¹³ represent a connection group, a single bond, or a double bond. The bonds between L¹¹ and Y¹², between L¹² and Y¹², between L¹² and Y¹¹, between L¹³ and Y¹¹, between L¹³ and Y¹³, and between L¹⁴ and Y¹³ represent a single bond or a double bond. n^Eπ represents an integer of 0 to 4. Formula (P-I) can be expressed preferably by Formula (P-2), Formula (P-9), Formula (P-IO), Formula (P-5), and Formula (I) described below. Formula (P-2)

Here, Pt represents a platinum ion and Y²¹ represents a connection group, a single bond, )r a double bond. Y²² and Y²³ represent a single bond or a connection bond. Q²¹ and Q²² ^•epresent an atom group constituting a nitrogen-containing heterocycle, and the bond between a ing formed by Q²¹ and Y²¹ and the bond between the ring formed by Q²² and Y²¹ represent a single bond or a double bond. X^E21 and X^E22 represent an oxygen atom, a sulfur atom, or a substituted or non-substituted nitrogen atom. R^E21, R^E22, R^E23, and R^E24 represent a hydrogen atom )r a substituent group, and R^E21, R^E22, R^E23 ₅ and R^E24 may form a ring by means of bonding, espectively. L²⁵ represents a ligand coordinating with the platinum ion. n^E21 represents an integer )f 0 to 4.

Formula (P-9)

Here, Pt represents a platinum ion, and Q^A1 and Q^ represent an atom group instituting a nitrogen-containing heterocycle. R^A1, R", R*³, and R^M represent a hydrogen atom >r a substituent group, and R^A1 and R^², and R*³ and R^M may form a ring by means of bonding, respectively. Y^ and Y^ represent a single bond or a connection bond. Y^A1 represent a connection bond, a single bond, or a double bond for connecting two bidentate ligands in a parenthesis. L^ represents a ligand coordinating with the platinum ion. n^A1 represents an integer of O to 4.

Formula (P-IO)

Here, Pt represents a platinum ion, Y^B2 represents a connection group and Y^B2 and Y^B3 represent a connection group or a single bond. X^B1 and X^B2 represent an oxygen atom, a sulfur atom, or a substituted or non-substituted nitrogen atom. n^B1 and n^B2 represent an integer of 0 or 1. R^B1, R^B2, R^B3, R^B4, R^B5, and R^Bδ represent a hydrogen atom or a substituent group, and R^B1 and R^B2, and R^B3 and R^B4 may form rings by means of bonding, respectively. L^B5 represents a ligand coordinating with the platinum ion. n^B3 represents an integer of 0 to 4. Here, Y^B1 is not connected to R^B5 or R^Bδ.

Formula (P-5)

Here, Pt represents a platinum ion, and Q⁵¹, Q⁵², Q⁵³, and Q⁵⁴ represent an atom group constituting a nitrogen-containing heterocycle. Y⁵¹ represents a connection group, a single bond or a double bond. W⁵¹ and W⁵² represent a substituted or non-substituted carbon atom or nitrogen atom. L⁵⁵ represents a ligand coordinating with the platinum ion. n^E51 represents an integer of 0 to 4. Formula (I)

In Formula (I), Z¹ and Z² represent a nitrogen-containing aromatic 6-membered ring of which a nitrogen atom coordinates with platinum. Q represents an aromatic 5-membered ring having one or two nitrogen atoms. L¹ and L² represent a single bond or a two-valence connection group, n represents 0 or 1.

Formula (P-2) described above can be expressed preferably by Formula (P-3) described below.

Formula (P-3)

In Formula (P-3), Z³¹, Z³², Z³³, Z³⁴, Z³⁵, Z³⁶, T³¹, T³², T³³, T³⁴, T³⁵, T³⁶, T³⁷ and T³⁸ represent a substituted or non-substituted carbon atom or nitrogen atom. X³¹ and X³² represent an oxygen atom, a sulfur atom, or a substituted or non-substituted nitrogen atom.

Formula (P-9) described above can be expressed preferably by Formulas (P-6) and (P-7) described below. Formula (P-6)

In Formula (P-6), Pt represents a platinum ion, and Q⁶¹ and Q⁶² represent an atom group constituting a ring. Z⁶¹, Z⁶², Z⁶³, Z⁶⁴, Z⁶⁵, Z⁶⁶, Z⁶⁷ and Z⁶⁸ represent a substituted or non- substituted carbon atom or nitrogen atom. Y⁶¹ represents a connection group, a single bond, or a double bond. Y⁶² and Y⁶³ represent a connection group or a single bond. L⁶⁵ represents a ligand coordinating with the platinum ion. n⁶¹ represents an integer of 0 to 4.

Formula (P-7)

In Formula (P-7), Pt represents a platinum ion, and Z⁷¹, Z⁷², Z⁷³, Z⁷⁴, Z⁷⁵, and Z⁷⁶ represent a substituted or non-substituted carbon atom or nitrogen atom. Y⁷¹, Y⁷², and Y⁷³ represent a connection group or a single bond. R⁷¹, R⁷², R⁷³, and R⁷⁴ represent a hydrogen atom or a substituent group, and R⁷¹ and R⁷², and R⁷³ and R⁷⁴ may form rings by means of bonding, respectively. L⁷⁵ represents a ligand coordinating with the platinum ion. n⁷¹ represents an integer of 0 to 4.

Formula (P-7) described above can be expressed preferably by Formula (P-11) described below.

Formula (P-I l)

Here, R^C1 and R^C2 represent a hydrogen atom or a substituent group., and R^C3, R⁰⁴, R^C5, and R^c6 represent a substituent group. n^C3 and n^C6 represent an integer of 0 to 3 and n⁰⁴ and n^C5 represent an integer of 0 to 4. When R^C3, R⁰⁴, R^C5, and R^C6 are plural, the plural R^C3, R⁰⁴, R^C5, and R^C6 may be equal to or different from each other, or may form a ring by means of bonding.

Formula (P-IO) described above can be expressed preferably by Formula (P- 12) described below.

Formula (P-12)

Here, R^D3 and R^D4 represent a hydrogen atom or a substituent group_s and R^D1 and R^D2 represent a substituent group. n^D1 and n^D2 represent an integer of 0 to 4. When R^D1 and R^D2 are plural, the plural R^D1 and R^D2 may be equal to or different from each other, or may form a ring by means of bonding. Y^D1 represents a vinyl group which is substituted at first and second positions, a phenylene ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, or a methylene group having a carbon number of 1 to 8.

Formula (I) described above can be expressed preferably by Formul-a.s (H), (IEI), and (IV) described below.

Formula (II)

In Formula (II), Z¹, Z², and L¹ are the same with those in Formula (I). R^P21 and R ,^]P22 represent a hydrogen atom or a substituent group, independently. Formula (TH)

In Formula (HI), Z\ Z², and L¹ are the same with those in Formula (I). R^P31, R^P32, and

R represent a hydrogen atom or a substituent group, independently. Formula (IV)

In Formula (IV), Z¹, Z², and L¹ are the same with those in Formula (I). R^P41 and R^P42 represent a hydrogen atom or a substituent group, independently. Formula (II) described above can be expressed preferably by Formula (HA) described below.

Formula (HA)

In Formula QIA), L¹ represents a single bond or a two-valence connection group* . R^P21, R^P22, R^P5\ R^p52, R^P53, R^P54, R^P55, and R^P56 represent a hydrogen atom or a substituent group* , independently.

Formula (HA) described above can be expressed preferably by Formula (IEB) described below.

Formula (IIB)

In Formula (HB), R^P21, R^P22, R^P5\ R^P52, R^rø, R^P54, R^P55, R^P56, R^P61, and R^P62 represent a hydrogen atom or a substituent group, independently.

Formula (IIB) described above can be expressed preferably by Formula (HC) described below.

Formula (HC)

In Formula (E-C), R^P21, R^P22, R^P51, R^P52, R^P53, R^P54, R^P55 ₃ and R^P56 represent a hydrogen atom or a substituent group, independently.

Formula (EC) described above can be expressed preferably by Formula (IID) described below.

Formula (ED)

In Formula (IID), R^p51, R^P52, R^P53 ₅ R^P54, R^P55 and R^P56 represent a hydrogen atom or a substituent group, independently. R^P21 represents a substituent group.

Formula (P-I) is described. Pt represents a platinum ion.

L¹¹, L¹², L¹³, and L¹⁴ represent a ligand coordinating with the platinum ion. Ar*. atom included in L¹¹, L¹², L¹³, and L¹⁴ and coordinating with the platinum ion is preferably a nirtrogen atom, an oxygen atom, a sulfur atom, or a carbon atom, and more preferably a nitrogen aΛom, an oxygen atom, or a carbon atom.

The bonds between the platinum ion and L¹¹, L¹², L¹³, and L¹⁴ may be a covalent bond, an ion bond, or a coordinate bond. The ligands including L¹¹, Y¹², L¹², Y¹¹, L¹³, Y¹³, and IL¹⁴, respectively, are preferably an anionic ligand (of which at least one anion is bonded to metal). The number of anions in the anionic hgand is preferably one of 1 to 3, more preferably 1 or 2, and most preferably 2

L¹¹, L¹², L¹³, and L¹⁴ of which a carbon atom coordinates with the platinum ion are not particularly limited, and examples thereof can include an imino hgand, an aromatic carbon-ring hgand (such as a benzene hgand, a naphthalene hgand, an anthracene hgand, and a phenanthracene hgand), and a heterocyclic hgand (such as a thiophene hgand, a pyridine hgand, a pyrazine hgand, a pyπmidine hgand, a thiazole hgand, an oxazole hgand, a pyrrole hgand, an imidazole hgand, a pyrazole hgand, condensed rings including them (such as a quinohne hgand and a benzothiazole hgand), and tautomers thereof)

Lⁿ, L¹², L¹³, and L¹⁴ of which a mtrogen atom coordinates with the platinum ion are not particularly limited, and examples thereof can include a nitrogen-containing heterocyclic hgand (such as a pyridine hgand, a pyrazine hgand, a pyπmidine hgand, a pyndazine hgand, a tπazine hgand, a thiazole hgand, an oxazole hgand, a pyrrole hgand, an imidazole hgand, a pyrazole hgand, a tπazole hgand, an oxadiazole hgand, a thiadiazole hgand, condensed rings including them (such as a quinoline hgand, a benzooxazole hgand, and a benzoiπudazole hgand), tautomers thereof, and an amino hgand (such as an alkyl ammo hgand (which has preferably a carbon number of 2 to 30, more preferably a carbon number of 2 to 20, and most preferably a carbon number of 2 to 10 and examples of which can include methylamino), an aryl amino hgand (such as phenylamino), an acyl ammo hgand (which has preferably a carbon number of 2 to 30, more preferably a carbon number of 2 to 20, and most preferably a carbon number of 2 to 10 and examples of which can include acetylamino and benzoylammo), an alkoxycarbonyl ammo hgand (which has preferably a carbon number of 2 to 30, more preferably a carbon number of 2 to 20, and most preferably a carbon number of 2 to 10 and examples of which can mclude methoxycarbonylamino), an aryloxycarbonyl amino hgand (which has preferably a carbon number of 7 to 30, more preferably a carbon number of 7 to 20, and most preferably a carbon number of 7 to 10 and examples of which can include phenyloxycarbonylamino), a sulfonyl ammo hgand (which has preferably a carbon number of 1 to 30, more preferably a carbon number of 1 to 20, and most preferably a carbon number of 1 to 10 and examples of which can mclude methane sulfonylamino and benzene sulfonylamino), and an imino hgand) Such hgands may be substituted again

L¹¹, L¹², L¹³, and L¹⁴ of which an oxygen atom coordmates with the platinum ion are not particularly limited, and examples thereof can mclude an alkoxy hgand (which has preferably a carbon number of 1 to 30, more preferably a carbon number of 1 to 20, and most preferably a carbon number of 1 to 10 and examples of which can include methoxy, ethoxy, butoxy, and 2- ethylhexyloxy), an aryloxy hgand (which has preferably a carbon number of 6 to 30, more preferably a carbon number of 6 to 20, and most preferably a carbon number of 6 to 12 and examples of which can include phenyloxy, 1-naphthyloxy, and 2-naphthyloxy), a heterocychc oxy ligand (which has preferably a carbon number of 1 to 30, more preferably a carbon number of 1 to 20, and most preferably a carbon number of 1 to 12 and examples of which can include pyridyloxy-. pyrazyloxy, pyrimidyloxy, and quinolyloxy), an acyloxy ligand (which has preferably a carbon number of 2 to 30, more preferably a carbon number of 2 to 20, and most preferably a carbon number of 2 to 10 and examples of which can include acetoxy and benzoyloxy), a silyloxy ligand (which has preferably a carbon number of 3 to 40, more preferably a carbon number of 3 to 30, and most preferably a carbon number of 3 to 24 and examples of which can include trimethyloxy and triphenylsilyloxy), a carbonyl ligand (examples of which can include a ketone ligand, an ester ligand, and an amide ligand), and an ether ligand (examples of which can include a dialkylether ligand, a diarylether ligand, and a furyl ligand).

L¹¹, L¹², L¹³, and L¹⁴ of which a sulfur atom coordinates with the platinum ion are not particularly limited, and examples thereof can include an alkylthio ligand (which has preferably a carbon number of 1 to 30, more preferably a carbon number of 1 to 20, and most preferably a carbon number of 1 to 12 and examples of which can include methylthio and ethylthio), an arylthio ligand (which has preferably a carbon number of 6 to 30, more preferably a carbon number of 6 to 20, and most preferably a carbon number of 6 to 12 and examples of which can include phenylthio), a heterocyclic thio ligand (which has preferably a carbon number of 1 to 30, more preferably a carbon number of 1 to 20, and most preferably a carbon number of 1 to 12 and examples of which can include pyridylthio, 2-benzimizolylthio, 2-benzoxazolylthio, and 2- benzthiazolylthio), a thiocarbonyl ligand (such as a thioketone ligand and a thioester ligand), and a thioether ligand (such as a dialkylthioether ligand, a diarylthioether ligand, and a thiofuryl ligand). The substituent ligands may be substituted again.

L¹¹ and L¹⁴ are preferably one of an aromatic carbon-ring ligand, an alkyloxy ligand, an aryloxy ligand, an ether ligand, an alkylthio ligand, an arylthio ligand, an alkylamino ligand, an arylamino ligand, an acylamino ligand, and a nitrogen-containing heterocyclic ligand (such as a pyridine ligand, a pyrazine ligand, a pyrimidine ligand, a pyridazine ligand, a triazine ligand, a thiazole ligand, an oxazole ligand, a pyrrole ligand, an imidazole ligand, a pyrazole ligand, a triazole ligand, an oxadiazole ligand, a thiadiazole ligand, condensed rings including them (such as a quinoline ligand, a benzooxazole ligand, and a benzimidazole ligand), and tautomers thereof), more preferably one of an aromatic carbon-ring ligand, an aryloxy ligand, an arylthio ligand, an arylamino ligand, an acylamino ligand, a pyridine ligand, a pyrazine ligand, an imidazole ligand, condensed rings including them (such as a quinoline ligand, a quinoxaline ligand, and a benzimidazole ligand), and tautomers thereof, still more preferably one of an aromatic carbon-ring ligand, an aryloxy ligand, an arylthio ligand, and an arylamino ligand, and most preferably one of an aromatic carbon-ring ligand and an aryloxy ligand. L¹² and L¹³ are preferably a ligand forming a coordinate bond with the platinum ion. The ligand forming a coordinate bond with the platinum ion is preferably one of a pyridine ring;, a pyrazine ring, a pyrimidine ring, a triazine ring, a thiazole ring, an oxazole ring, a pyrrole ring, a triazole ring, condensed rings including them (such as a quinoline ring, a benzooxazole ring, a benzimidazole ring, and an indolenine ring), and tautomers thereof, more preferably one of a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyrrole ring, condensed rings including thein (such as a quinoline ring and a benzopyrrole ring), and tautomers thereof, and most preferably one of a pyridine ring and condensed rings including the pyridine ring (such as a quinoline ring).

L¹⁵ represents a ligand coordinating with the platinum ion. L¹⁵ is preferably a ligand. of monodentate to quadridentate and an anionic ligand of monodentate to quadridentate. The anioxήc ligand of monodentate to quadridentate is not particularly limited, but is preferably one of a halogen ligand, a 1,3-diketone ligand (such as an acetyl acetone ligand), a monoanionic bidenta^~te ligand (such as a picoline acid ligand and a 2-(2-hydroxyphenyl)-pyridine ligand) containing a pyridine ligand, and a quadridentate ligand formed by L¹¹, Y¹², L¹², Y¹¹, L¹³, Y¹³, and L¹⁴, more preferably one of a 1,3-diketone ligand (such as an acetyl acetone ligand), a monoanionic bidentate ligand (such as a picoline acid ligand and a 2-(2-hydroxyphenyl)-pyridine ligand) containing a pyridine ligand, and a quadridentate ligand formed by L¹¹, Y¹², L¹², Y¹¹, L¹³, Y¹³, and L¹⁴, still more preferably one of a 1,3-diketone ligand (such as an acetylacetone ligand), and a monoanionic bidentate ligand (such as a picoline acid ligand and a 2-(2-hydroxyphenyl)-pyridin.e ligand) containing a pyridine ligand, and most preferably a 1,3-diketone ligand (such as an acetylacetone ligand). The number of dentates and the number of ligands are not greater than ttae coordination number of metal. L¹⁵ does not form a cyclic ligand by means of the coupling to both ofL¹¹ and L¹⁴

Y¹¹, Y¹², and Y¹³ represent a connection group, a single bond, or a double bond. Thes connection group is not particularly limited, but is preferably a carbonyl connection group, a thiocarbonyl connection group, an alkylene group, an alkenylene group, an arylene group, a heteroarylene group, an oxygen atom connection group, a nitrogen atom connection group, a silicon atom connection group, and a group obtained by combining them. The bonds between L_* ⁿ and Y¹², between L¹² and Y¹², between L¹² and Y¹¹, between L¹³ and Y¹¹, between L¹³ and Y¹³, and between L¹⁴ and Y¹³ represent a single bond or a double bond.

Yⁿ, Y¹², and Y¹³ are preferably one of a single bond, a double bond, a carbonyl connection group, an alkylene connection group, and an alkenylene group. Y¹¹ is more preferably one of a single bond and an alkylene connection group and still more preferably an alkylene connection group. Y¹² and Y¹³ are more preferably a single bond and an alkenylene group and still more preferably a single bond. A ring formed by Y¹², L¹¹, L¹², and a platinum ion, a ring formed by Y¹¹, L¹², L¹³, and a platinum ion, and a ring formed by Y¹³, L¹³, L¹⁴, and a platinum ion have preferably a ring member number of 4 to 10, more preferably a ring member number of 5 to 7, and most preferably a ring member number of 5 or 6. n^Eπ represents an integer of 0 to 4. When the coordination number of the platinum ion is 4, n^En is preferably 0. When the coordination number of the platinum ion is 6, n^Eπ is preferably 1 or 2 and more preferably 1. When the coordination number of the platinum ion is 6 and n^Eπ is 1, L¹⁵ represents a bidentate ligand. When the coordination number of the platinum ion is 6 and n^Eπ is 2, L¹⁵ represents a monodentate ligand. When n^Eπ is plural, plural L¹⁵ may be equal to or different from each other.

Formula (P-2) is now described.

Q²¹ and Q²² represent an atom group forming a nitrogen-containing heterocycle (a ring containing nitrogen coordinating with a platinum ion). The nitrogen-containing heterocycle formed by Q²¹ and Q²² is not particularly limited, and examples thereof can include a pyridine ring, a pyrazine ring, a pyrimidine ring, a triazine ring, a thiazole ring, an oxazole ring, a pyrrole ring, a triazole ring, condensed rings including them (such as a quinoline ring, a benzooxazole ring, a benzimidazole ring, and an indolenine ring), and tautomers thereof.

The nitrogen-containing heterocycle formed by Q²¹ and Q²² is preferably one of a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, a triazine ring, a pyrazole ring, an imidazole ring, an oxazole ring, a pyrrole ring, a benzoazole ring, condensed rings including them (such as a quinoline ring, a benzooxazole ring, and a benzoimidazole ring), and tautomers thereof, more preferably one of a pyridine ring, a pyrazine ring, a pyrimidine ring, an imidazole ring, a pyrrole ring, condensed rings including them (such as a quinoline ring), and tautomers thereof, still more preferably one of a pyridine ring and a condensed ring thereof (such as a quinoline ring), and most preferably a pyridine ring.

X^E21 and X^E22 are preferably one of an oxygen atom, a sulfur atom, and a substituted or non-substituted nitrogen atom, more preferably one of an oxygen atom, a sulfur atom, and a substituted nitrogen atom, still more preferably one of an oxygen atom and a sulfur atom, and most preferably an oxygen atom.

Y²¹ is the same with Y¹¹ described above and a preferable range thereof is also the same.

Y²² and Y²³ represent a connection group or a single bond, and are preferably a single bond. The connection group is not particularly limited, but is preferably one of a carbonyl connection group, a tbiocarbonyl connection group, an alkylene group, an alkenylene group, an arylene group, a heteroarylene group, an oxygen atom connection group, a nitrogen atom connection group, and a group obtained by combining them. The connection group is preferably one of a carbonyl connection group, an alkylene connection group, and an alkenylene connection group, more preferably one of a carbonyl connection group and an alkylene connection group, and most preferably a carbonyl connection group.

R^E21, R^E22, R^E23, and R^E24 represent a hydrogen atom or a substituent group. The substituent group is not limited, and examples thereof can include an alkyl group (which has preferably a carbon number of 1 to 30, more preferably a carbon number of 1 to 20, and most preferably a carbon number of 1 to 10, and examples of which can include methyl, ethyl, iso- propyl, tert-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, and cyclohexyl), an alkenyl group (which has preferably a carbon number of 2 to 30, more preferably a carbon number of 2 to 20, and most preferably a carbon number of 2 to 10, and examples of which can include vinyl, aryl, 2-butenyl, and 3-pentenyl), an alkinyl group (which has preferably a carbon number of 2 to 30, more preferably a carbon number of 2 to 20, and most preferably a carbon number of 2 to 10, and examples of which can include propargyl and 3-pentinyl), an aryl group (which has preferably a carbon number of 6 to 30, more preferably a carbon number of 6 to 20, and most preferably a carbon number of 6 to 12, and examples of which can include phenyl, p- methylphenyl, naphthyl, and anthranil), and an amino group (which has preferably a carbon number of 0 to 30, more preferably a carbon number of 0 to 20, and most preferably a carbon number of 0 to 10, and examples of which can include amino, methyl amino, dimethyl amino, diethyl amino, dibenzyl amino, diphenyl amino, and ditolyl amino).

Other examples of the substituent group can include an alkoxy group (which has preferably a carbon number of 1 to 30, more preferably a carbon number of 1 to 20, and most preferably a carbon number of 1 to 10, and examples of which can include methoxy, ethoxy, butoxy, and 2-ethylhexyloxy), an aryloxy group (which has preferably a carbon number of 6 to 30, more preferably a carbon number of 6 to 20, and most preferably a carbon number of 6 to 12, and examples of which can include phenyloxy, 1-naphtayloxy, and 2-naphthyloxy), a heterocyclic oxy group (which has preferably a carbon number of 1 to 30, more preferably a carbon number of 1 to 20, and most preferably a carbon number of 1 to 12, and examples of which can include pyridyloxy, pyrazyloxy, pyrimidyloxy, and quinolyloxy), an acyl group (which has preferably a carbon number of 1 to 30, more preferably a carbon number of 1 to 20, and most preferably a carbon number of 1 to 12, and examples of which can include acetyl, benzoyl, formyl, and pivaloyl), an alkoxycarbonyl group (which has preferably a carbon number of 2 to 30, more preferably a carbon number of 2 to 20, and most preferably a carbon number of 2 to 12, and examples of which can include methoxycarbonyl and ethoxycarbonyl), and an aryloxycarbonyl group (which has preferably a carbon number of 7 to 30, more preferably a carbon number of 7 to 20, and most preferably a carbon number of 7 to 12, and examples of which can include phenyloxycarbonyl) .

Other examples of the substituent group can include an acyloxy group (which has preferably a carbon number of 2 to 30, more preferably a carbon number of 2 to 20, and most preferably a carbon number of 2 to 10, and examples of which can include acetoxy and benzoyloxy), an acyl amino group (which has preferably a carbon number of 2 to 30, more preferably a carbon number of 2 to 20, and most preferably a carbon number of 2 to 10, and examples of which can include acetyl amino and benzoyl amino), an alkoxycarbonyl amino group (which has preferably a carbon number of 2 to 30, more preferably a carbon number of 2 to 20, and most preferably a carbon number of 2 to 12, and examples of which can include methoxycarbonyl amino), an aryloxycarbonyl amino group (which has preferably a carbon number of 7 to 30, more preferably a carbon number of 7 to 20, and most preferably a carbon number of 7 to 12, and examples of which can include phenyloxycarbonyl amino), a sulfonyl amino group (which has preferably a carbon number of 1 to 30, more preferably a carbon number of 1 to 20, and most preferably a carbon number of 1 to 12, and examples of which can include methane sulfonyl amino and benzene sulfonyl amino), and a sulfamoyl group (which has preferably a carbon number of 0 to 30, more preferably a carbon number of 0 to 20, and most preferably a carbon number of 0 to 12, and examples of which can include sulfamoyl, methylsulfamoyl, dimethylsulfamoyl, and phenylsulfamoyl).

Other examples of the substituent group can include a carbamoyl group (which has preferably a carbon number of 1 to 30, more preferably a carbon number of 1 to 20, and most preferably a carbon number of 1 to 12, and examples of which can include carbamoyl, methylcarbamoyl, diethylcarbamoyl, and phenylcarbamoyl), an alkylthio group (which has preferably a carbon number of 1 to 30, more preferably a carbon number of 1 to 20, and most preferably a carbon number of 1 to 12, and examples of which can include methylthio and ethylthio), an arylthio group (which has preferably a carbon number of 6 to 30, more preferably a carbon number of 6 to 20, and most preferably a carbon number of 6 to 12, and examples of which can include phenylthio), a heterocyclic thio group (which has preferably a carbon number of 1 to 30, more preferably a carbon number of 1 to 20, and most preferably a carbon number of 1 to 12, and examples of which can include pyridylthio, 2-benzimizolylthio, 2-benzoxazolylthio, and 2- benzthiazolylthio), a sulfonyl group (which has preferably a carbon number of 1 to 30, more preferably a carbon number of 1 to 20, and most preferably a carbon number of 1 to 12, and examples of which can include mesyl and tosyl), a sulfϊnyl group (which has preferably a carbon number of 1 to 30, more preferably a carbon number of 1 to 20, and most preferably a carbon number of 1 to 12, and examples of which can include methane sulfinyl and benzene sulfϊnyl), and an ureido group (which has preferably a carbon number of 1 to 30, more preferably a carbon number of 1 to 20, and most preferably a carbon number of 1 to 12, and examples of which can include ureido, methylureido, and phenylureido).

Other examples of the substituent group can include an amide phosphate group (which has preferably a carbon number of 1 to 30, more preferably a carbon number of 1 to 20, and most preferably a carbon number of 1 to 12, and examples of which can include diethyl amide phosphate and phenyl amide phosphate), an hydroxyl group, a mercapto group, a halogen atom (examples of which can include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom), a cyano group, a sulfo group, a carboxyl group, a nitro group, a hydroxamic group, a sulfino group, a hydrazino group, an imino group, a heterocyclic group (which has preferably a carbon number of 1 to 30 and more preferably a carbon number of 1 to 12 and which includes, for example, a nitrogen atom, an oxygen atom, and a sulfur atom as the hetero atom, examples of which can include imidazolyl, pyridyl, quinolyl, furyl, thienyl, piperidyl, morpholino, benzoxazolyl, benzimidazolyl, benztbiazolyl, carbazolyl, and azepinyl), a silyl group (which has preferably a carbon number of 3 to 40, more preferably a carbon number of 3 to 30, and most preferably a carbon number of 3 to 24, and examples of which can include trimethylsilyl and triphenylsilyl), and a silyloxy group (which has preferably a carbon number of 3 to 40, more preferably a carbon number of 3 to 30, and most preferably a carbon number of 3 to 24, and examples of which can include methylsilyloxy and triphenylsilyloxy). These substituent groups may be substituted again.

R^E21, R^E22, R^E23, and R^E24 are preferably groups forming a ring structure (such as a benzo condensed ring and a pyridine condensed ring) in which an alkyl group, an aryl group, and R^E21 and R^E22 or R^E23 and R^E24 are bonded, and more preferably groups forming a ring structure (such as a benzo condensed ring and a pyridine condensed ring) in which R^E21 and R^E22 or R^E23 and R^E24 are bonded.

L²⁵ is the same with L¹⁵ described above and a preferable range thereof is also the same. n^E21 is the same with n^Eπ described above and a preferable range thereof is also the same.

In Formula (P-2), a metal complex that the ring formed by Q²¹ and Q²² is a pyridine ring and Y²¹ is a connection group, a metal complex that the ring formed by Q²¹ and Q²² is a pyridine ring, Y²¹ is a single bond or a double bond, and X^E21 and X^E22 are a sulfur atom or a substituted or non-substituted nitrogen atom, or a metal complex that the ring formed by Q²¹ and Q²² is a nitrogen-containing five-membered heterocycle or a nitrogen-containing six-membered heterocycle having two nitrogen atoms is preferable.

Formula (P-3) is now described.

Z³¹, Z³², Z³³, Z³⁴, Z³⁵, and Z³⁶ are a substituted or non-substituted carbon atom or nitrogen atom and preferably a substituted or non-substituted carbon atom. Examples of the substituent group on a carbon atom can include the groups described with reference to R^E21. Z³¹ and Z³², Z³² and Z³³, Z³³ and Z³⁴, Z³⁴ and Z³⁵, and Z³⁵ and Z³⁶ may be bonded to each other through connection groups, respectively, to form condensed rings (such as a benzo condensed ring and a pyridine condensed ring). Z³¹ and T³¹, and Z³⁶ and T³⁸ may be bonded to each other through connection groups, respectively, to form condensed rings (such as a benzo condensed ring and a pyridine condensed ring).

The substituent group on the carbon atom is preferably one of an alkyl group, an alkoxy group, an alkylamino group, an aryl group, a group forming a condensed ring (such as a benzo condensed ring and a pyridine condensed ring), and a halogen atom, more preferably one of an alkylamino group, an aryl group, and a group forming a condensed ring (such as a benzo condensed ring and a pyridine condensed ring), still more preferably one of an aryl group and a group forming a condensed ring (such as a benzo condensed ring and a pyridine condensed ring), and most preferably a group forming a condensed ring (such as a benzo condensed ring and a pyridine condensed ring).

T³¹, T³², T³³, T³⁴, T³⁵, T³⁶, T³⁷, and T^3S are preferably a substituted or non-substituted carbon atom or nitrogen atom, and more preferably a substituted or non-substituted carbon atom. The substituent group on a carbon atom can include the groups described with reference to R^E21. T³¹ and t³², T³² and t³³, T³³ and t³⁴, T³⁵ and Z³⁶, T³⁶ and Z³⁷, and t³⁷ and t³⁸ may be bonded to each other through connection groups, respectively, to form condensed rings (such as a benzo condensed ring).

The substituent group on the carbon atom is preferably one of an alkyl group, an alkoxy group, an alkylamino group, an aryl group, a group forming a condensed ring (such as a benzo condensed ring and a pyridine condensed ring), and a halogen atom, more preferably one of an aryl group, a group forming a condensed ring (such as a benzo condensed ring and a pyridine condensed ring), and a halogen atom, still more preferably one of an aryl group and a halogen atom, and most preferably an aryl group.

X³¹ and X³² are the same with X^E21 and X^E22 described above, respectively, and preferable ranges thereof are also the same.

Formula (P-5) is now described.

Q⁵¹ and Q⁵² are the same with Q²¹ and Q²² described above, respectively, and preferable ranges thereof are also the same.

Q⁵³ and Q⁵⁴ represent a group forming a nitrogen-containing heterocycle (a ring containing nitrogen coordinating with the platinum ion). The nitrogen-containing heterocycle formed by Q⁵³ and Q⁵⁴ is not particularly limited, but preferably one of a tautomer of a pyrrole derivative, a tautomer of an imidazole derivative, a tautomer of a thiazole derivative, and a tautomer of an όxazole derivative, more preferably one of a tautomer of a pyrrole derivative, a tautomer of an imidazole derivative, and a tautomer of a thiazole derivative, still more preferably one of a tautomer of a pyrrole derivative and a tautomer of an imidazole derivative, and most preferably a tautomer of a pyrrole derivative.

Y⁵¹ is the same with Y¹¹ described above and a preferable range thereof is also the same.

L⁵⁵ is the same with L¹⁵ described above and a preferable range thereof is also the same. n^E51 is the same with n^En described above and a preferable range thereof is also the same.

W⁵¹ and W⁵² are preferably a substituted or non-substituted carbon atom or nitrogen atom, more preferably a non-substituted carbon atom or nitrogen atom, and still more preferably a non-substituted carbon atom.

Formula (P-9) is now described. Q^A1, Q*², Y^A1, Y*², Y*³, R^A1, R*², R*³, R^A4, L*⁵, and n^A1 are the same with M²¹, Q²¹, Q²², Y²¹, Y²², Y²³, R^E21, R^E22, R^E23, R^E24, L²⁵, and n^E21 in Formula (P-2) and preferable ranges thereof are also the same.

Formula (P -6) is now described.

Q⁶¹ and Q⁶² represent a group forming a ring. The ring formed by Q^S1 and Q⁶² is not limited, and examples thereof can include a benzene ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, a thiophene ring, an isothiazole ring, a furan ring, an isooxazole ring, and condensed rings thereof.

The ring formed by Q⁶¹ and Q⁶² is preferably one of a benzene ring, a pyridine ring, a thiophene ring, a thiazole ring, and condensed rings thereof, more preferably one of a benzene ring, a pyridine ring, and condensed rings thereof, and most preferably a benzene ring and a condensed ring thereof.

Y⁶¹ is the same with Y¹¹ and a preferable range thereof is also the same.

Y⁶² and Y⁶³ represent a connection group or a single bond. The connection group is not particularly limited, and examples thereof can include a carbonyl connection group, a thiocarbonyl connection group, an alkylene group, an alkenylene group, an arylene group, a heteroarylene group, an oxygen atom connection group, a nitrogen atom connection group, and a group obtained by combining them.

Y⁶² and Y⁶³ are preferably one of a single bond, a carbonyl connection group, an alkylene connection group, and an alkenylene connection group, more preferably one of a single bond and an alkenylene connection group, and most preferably a single bond.

L⁶⁵ is the same with L¹⁵ described above and a preferable range thereof is also the same. n⁶¹ is the same with n^Eπ described above and a preferable range thereof is also the same.

Z⁶¹, Z⁶², Z⁶³, Z⁶⁴, Z⁶⁵, Z⁶⁵, Z⁶⁷, and Z⁶⁸ are a substituted or non-substituted carbon atom or nitrogen atom and preferably a substituted or non-substituted carbon atom. Examples of the substituent group on a carbon atom can include the groups described with reference to R^E21. Z⁶¹ and Z⁶², Z⁶² and Z⁶³, Z⁶³ and Z⁶⁴, Z⁶⁵ and Z⁶⁶, Z⁶⁶ and Z⁶⁷, and Z⁶⁷ and Z⁶⁸ may ^"be bonded to each other through connection groups, respectively, to form condensed rings (such as a benzo condensed ring and a pyridine condensed ring). The ring formed by Q⁶¹ and Q⁶² may be bonded to Z⁶¹ and Z⁶⁸ through connection groups, respectively, to form rings.

The substituent group on the carbon atom is preferably one of an albyl group, an alkoxy group, an alkylamino group, an aryl group, a group forming a condensed ring (such as a benzo condensed ring and a pyridine condensed ring), and a halogen atom, more preferably one of an alkylamino group, aryl group, and a group forming a condensed ring (such as a benzo condensed ring and a pyridine condensed ring), still more preferably one of an aryl group aund a group forming a condensed ring (such as a benzo condensed ring and a pyridine condensed ring), and most preferably a group forming a condensed ring (such as a benzo condensed ring and a pyridine condensed ring).

Formula (P-T) is now described.

Y⁷¹, Y⁷², and Y⁷³ are the same with Y⁶² and preferable ranges thereof are also the same.

L⁷⁵ is the same with L¹⁵ described above and a preferable range thereof is also the same. n⁷¹ is the same with n^Eπ described above and a preferable range thereof is also the same.

Z⁷¹, Z⁷², Z⁷³, Z⁷⁴, Z⁷⁵, and Z⁷⁶ are a substituted or non-substituted carbon atom or nitrogen atom and preferably a substituted or non-substituted carbon atom. Examples of the substituent group on a carbon atom can include the groups described with reference to R^E21. Z⁷¹ and Z⁷², and Z⁷³ and Z⁷⁴ may be bonded to each other through connection groups, respectively, to form condensed rings (such as a benzo condensed ring and a pyridine condensed ring).

R⁷¹ to R⁷⁴ are the same with the substituent groups of R^E21 to R^E24 in .Formula (P-2) and preferable ranges thereof are also the same.

Formula (P-Il) is now described.

R^cl and R^C2 are a hydrogen atom or a substituent group and examples of the substituent group preferably include an alkyl group and an aryl group described as the subs"tituent groups of R^E21 to R^E24 in Formula (P-2). The substituent groups representd by R⁰³, R⁰⁴. R.^C5, and R^C6 are the same with the substituent groups of R^E21 in Formula (P-2). n^C3 and n^c6 are an integer of 0 to 3 and n⁰⁴ and n^C5 are an integer of 0 to 4. When R^C3, R⁰⁴, R^C5, and R^c6 are plural, respectively, the plural R^C3, R⁰⁴, R^c5, and R^C6 may be equal or different. R^C3, R⁰⁴, R^C5, and R^C6 axe preferably one of an alkyl group, an aryl group, a hetero aryl group, and a halogen atom.

Formula (P-IO) is now described.

Y^B2, Y^B3, R^BI, R^B2, R^B3, R^B4, L^B5, n^B3, X^B1, and X^B2 are the same mth Y²², Y²³, R^E21, R^E22, R^E23 ₅ R^E24, L²⁵, n^E21, X^E21, and X^E22 in Formula (P-2). Y^B1 represents a connection group and is the same with Y²¹ in Formula (P-2), which is preferably one of a vinyl group which is substituted at first and second positions, a phenylene ring, a pyridine ring, a pyrazine ring, a P3τimidine ring, and a methylene group having a carbon number of 1 to 8. R^B5 and R^B6 are a hydrogen atom or a substituent group, and examples of the substituent group can include an alkyl group, an aryl group, and a heterocyclic group described as the substituent groups of R^E21, in Formula. (P-2). However, Y^B1 is not connected to R^B5 or R^B6. n^B1 and n^B2 are an integer of 0 or 1.

Formula (P- 12) is now described.

The substituent groups representd by R^D1, R^D2, R^D3, and R^D4 are the same with the substituent groups representd by R^B5 or R^B6 in Formula (P-IO) and preferable ranges thereof are also the same. n^D1 and n^D2 are an integer of 0 to 4. Y^D1 is a vinyl group which is substituted at first and second positions, a phenylene ring, a pyridine ring, a pyrazine ring, a p5^imidine ring, or a methylene group having a carbon number of 1 to 8.

Substituent group A in the present specification can be defined as follows in the following explanation of the compounds group.

(Substituent Group A) an alkyl group (which has preferably a carbon number of 1 to 30, more preferably a carbon number of 1 to 20, and most preferably a carbon number of 1 to 10, and examples of which can include methyl, ethyl, iso-propyl, tert-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, and cyclohexyl), an alkenyl group (which has preferably a carbon number of 2 to 30, more preferably a carbon number of 2 to 20, and most preferably a carbon number of 2 to 10, and examples of which can include vinyl, aryl, 2-butenyl, and 3-pentenyl), an alkinyl group (which has preferably a carbon number of 2 to 30, more preferably a carbon number of 2 to 20, and most preferably a carbon number of 2 to 10, and examples of which can include propargyl and 3-pentinyl), an aryl group (which has preferably a carbon number of 6 to 30, more preferably a carbon number of 6 to 20, and most preferably a carbon number of 6 to 12, and examples of which can include phenyl, p-methylphenyl, naphthyl, and anthranil), an amino group (which has preferably a carbon number of 0 to 30, more preferably a carbon nuirϊber of 0 to 20, and most preferably a carbon number of 0 to 10, and examples of which can include amino, methyl amino, dimethyl amino, diethyl amino, dibenzyl amino, diphenyl amino, aaid ditolyl amino), an alkoxy group (which has preferably a carbon number of 1 to 30, more preferably a carbon number of 1 to 20, and most preferably a carbon number of 1 to 10, and examples of which can include methoxy, ethoxy, butoxy, and 2-ethylhexyloxy), an aryloxy group (which has preferably a carbon number of 6 to 30, more preferably a carbon number of 6 to 20, and most preferably a carbon number of 6 to 12, and examples of which can include phenyloxy, 1- naphtayloxy, and 2-naphthyloxy), and a heterocyclic oxy group (which has prefeiably a carbon number of 1 to 30, more preferably a carbon number of 1 to 20, and most preferably a carbon number of 1 to 12, and examples of which can include pyridyloxy, pyrazyloxy, p;yrimidyloxy, and quinolyloxy). An acyl group (which has preferably a carbon number of 1 to 30, more preferably a carbon number of 1 to 20, and most preferably a carbon number of 1 to 12, and examples of which can include acetyl, benzoyl, formyl, and pivaloyl), an alkoxycarbonyl group (which has preferably a carbon number of 2 to 30, more preferably a carbon number of 2 to 20, and most preferably a carbon number of 2 to 12, and examples of which can include methoxycarbonyl and ethoxycarbonyl), an aryloxycarbonyl group (which has preferably a carbon number of 7 to 30, more preferably a carbon number of 7 to 20, and most preferably a carbon number of 7 to 12, and examples of which can include phenyloxycarbonyl), an acyloxy group (which has preferably a carbon number of 2 to 30, more preferably a carbon number of 2 to 20, and most preferably a carbon number of 2 to 10, and examples of which can include acetoxy and benzoylox^), an acyl amino group (which has preferably a carbon number of 2 to 30, more preferably a carbon number of 2 to 20, and most preferably a carbon number of 2 to 10, and examples of which can include acetyl amino and benzoyl amino), an alkoxycarbonyl amino group (which has preferably a carbon number of 2 to 30, more preferably a carbon number of 2 to 20, and most preferably a carbon number of 2 to 12, and examples of which can include methoxycarbonyl amino), and an aryloxycarbonyl amino group (which has preferably a carbon number of 7 to 30, more preferably a carbon number of 7 to 20, and most preferably a carbon number of 7 to 12, and examples of which can include phenyloxycarbonyl amino).

A sulfonyl amino group (which has preferably a carbon number of 1 to 30, more preferably a carbon number of 1 to 20, and most preferably a carbon number of 1 to 12, and examples of which can include methane sulfonyl amino and benzene sulfonyl amino), a. sulfamoyl group (which has preferably a carbon number of 0 to 30, more preferably a carbon number of 0 to 20, and most preferably a carbon number of 0 to 12, and examples of which can include sulfamoyl, methylsulfamoyl, dimethylsulfamoyl, and phenylsulfamoyl), a carbamoyl group (whibli has preferably a carbon number of 1 to 30, more preferably a carbon number of 1 to 20, and most preferably a carbon number of 1 to 12, and examples of which can include carbamoyl., methylcarbamoyl, diethylcarbamoyl, and phenylcarbamoyl), an alkylthio group (whicfci has preferably a carbon number of 1 to 30, more preferably a carbon number of 1 to 20, aaid most preferably a carbon number of 1 to 12, and examples of which can include methylthio and ethylthio), an arylthio group (which has preferably a carbon number of 6 to 30, more preferably a carbon number of 6 to 20, and most preferably a carbon number of 6 to 12, and examples of which can include phenylthio), a heterocyclic thio group (which has preferably a carbon nunxber of 1 to 30, more preferably a carbon number of 1 to 20, and most preferably a carbon nυmbex of 1 to 12, and examples of which can include pyridylthio, 2-benzimizolylthio, 2-benzoxazolylthio, and 2- benzthiazolylthio), and a sulfonyl group (which has preferably a carbon number of 1 to 30, more preferably a carbon number of 1 to 20, and most preferably a carbon number of 1 to 12, an<i examples of which can include mesyl and tosyl).

A sulfinyl group (which has preferably a carbon number of 1 to 30, more prefera_bly a carbon number of 1 to 20, and most preferably a carbon number of 1 to 12, and examples of which can include methane sulfinyl and benzene sutfinyl), an ureido group (which has preferably a. carbon number of 1 to 30, more preferably a carbon number of 1 to 20, and most preferably a carbon number of 1 to 12, and examples of which can include ureido, methylureido, and phenylureido), an amide phosphate group (which has preferably a carbon number of 1 to 3O, more preferably a carbon number of 1 to 20, and most preferably a carbon number of 1 to 12, and examples of which can include diethyl amide phosphate and phenyl amide phosphate), an hydroxyl group, a mercapto group, a halogen atom (examples of which can include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom), a cyano group, a sulfo group, s. carboxyl group, a nitro group, a hydroxamic group, a sulfino group, a hydrazino group, an imino group, a heterocyclic group (which has preferably a carbon number of 1 to 30 and more pr&ferably a carbon number of 1 to 12 and which includes, for example, a nitrogen atom, an oxygen atom, and a sulfur atom as the hetero atom, examples of which can include imidazolyl, pyridyl, qn-inolyl, furyl, thienyl, piperidyl, morpholino, benzoxazolyl, benzirnidazolyl, benzthiazolyl, carbazol^l, and azepinyl), a silyl group (which has preferably a carbon number of 3 to 40, more preferably s. carbon number of 3 to 30, and most preferably a carbon number of 3 to 24, and examples odf which can include trimethylsilyl and triphenylsilyl), and a silyloxy group (which has preferably a carbon number of 3 to 40, more preferably a carbon number of 3 to 30, and most preferably a carbon number of 3 to 24, and examples of which can include methylsilyloxy andtriphenylsilyloxy). These substituent groups may be substituted again.

The groups of Substituent group A or the groups in Formulas (I), (II), (III), (TV), (HA), (HB), (HC) and (HD) described below (R^P21, R^P22, R^P31, R^P32, R^P33, R^p41, R^P42, R^P51, R^P52, R^PS3, R^PS4, R^P55, R^P56, R^P61, and R^P62 are preferably selected from the following group: an alkyl group having a carbon number of 1 to 20, an alkenyl group having a carbon number of 2 to 10, an aryl group having a carbon number of 6 to 20, an amino group having a carbon number of 2 to 20, an jaJkoxy group having a carbon number of 1 to 20, an aryloxy group having a carbon number of 6 to 20, an acyl group having a carbon number of 2 to 20, an alkoxycarbonyl group having a carbon nimmber of 2 to 20, an alkylthio group having a carbon number of 1 to 20, an arylthio group having a. carbon number of 6 to 20, a sulfonyl group having a carbon number of 1 to 20, a hydroxyl group, a halogen atom, a cyano group, a nitro group, and a heterocyclic group having a ring member number of 5 to 7.

The complex represented by Formula (I) is now described. In Formula (I), Z¹ ancfi Z² represent a nitrogen-containing 6-membered aromatic ring of which a nitrogen atom coordinates with platinum. Q represents a 5-membered aromatic ring containing one or two nitrogen atom. L¹ and L² represent a single bond or a connection group, n represents 0 or 1.

Z¹ and Z² represent a nitrogen-containing 6-membered aromatic ring of which a nitrogen atom coordinates with platinum. Z¹ and Z² are preferably one of pyridine, pyrazine, pyrimidine, pyridazine, and triazine, more preferably pyridine, pyrazine, and pyrimidine, still more preferably pyridine and pyrazine, and most preferably a pyridine. Z¹ and Z² may be equal to or different from each other. Z¹ and Z² may have a substituent group selected from the groups of Substituent group A.

The substituent group which Z¹ and Z² may have is preferably an alkyl group, an aryl group, an amino group, an alkoxy group, an aryloxy group, an acyl group, an alkoxycarbonyl group, an alkylthio group, a sulfonyl group, a hydroxy! group, a halogen atom, a cyano group, a nitro group, and a heterocyclic group.

Z¹ and Z² may form a condensed ring with another ring. Examples of the ring to be condensed can include a benzene ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, a thiophene ring, a furan ring, a pyrrole ring, an imidazole ring, a pyrazole ring, a triazole ring, an oxazole ring, a thiazole ring, an oxadiazole ring, and a thiadiazole ring.

Z¹ and Z² are preferably one of a substituted or non-substituted pyridine ring, a pyrazine ring, and a pyrimidine ring, more preferably one of a non-substituted pyridine ring and a pyrazine ring, and still more preferably a non-substituted pyridine ring.

Q represents a nitrogen-containing 5-membered aromatic ring having one or two nitrogen atoms. That is, Q represents a group forming the nitrogen-containing 5-membered aromatic ring having one or two nitrogen atoms along with a carbon atom and a nitrogen atom expressed in Z^N-C-Pt (or Z²-N-C-Pt). Examples of Q can include (non-)substituted pyrrole, pyrazole, and imidazole. Q is preferably one of (non-)substituted pyrrole and pyrazole, more preferably (non-)substituted pyrazole, still more preferably pyrazole having a substituent group at the third position, still more preferably pyrazole having an alkyl group or a cyano group at the third position, and most preferably pyrazole having a trifluoromethyl group, a t-butyl group, or a cyano group.

Q may have a substituent group and the substituent group is the same with those of Substituent group A. The substituent group of Q is preferably one of an alkyl group, an aryl group, a heterocyclic group, and a cyano group, more preferably one of an alkyl group and a cyano group, and still more preferably one of a trifluoromethyl group, a t-butyl group, and a cyano group.

Q may form a condensed ring with another ring. Examples of the ring to be condensed can include a benzene ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, a thiophene ring, a furan ring, a pyrrole ring, an imidazole ring, a pyrazole ring, a triazole ring, an oxazole ring, a thiazole ring, an oxadiazole ring, and a thiadiazole ring. L¹ and L² represent a single bond or a 2-valence connection group, n represents 0 or 1. n is preferably 0. That is, when n is 0, two Q's do not form a ring by means of bonding. The 2- valence connection group is not particularly limited, but preferably a connection group including a. carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom or a silicon atom. Specific examples of the 2-valence connection group are described below, but the present invention is not limited to the examples.

These connection groups may further have a substituent group and the substituent groups of Z¹ and Z² can be used as the substituent group to be introduced

L¹ is preferably one of a dialkyl methylene group, a diaryl methylene group, and diheteroaryl methylene group, more preferably one of a dimethyl methylene group and a diphenyl methylene group, and most preferably a dimethyl methylene group. L² is preferably one of a dialkyl methylene group, a diaryl methylene group, an ethylene group, a dialkyl ethylene group, a trialkyl ethylene group, a tetraalkyl ethylene group and a tetraaryl ethylene group, more preferably one of a dialkyl methylene group, a diaryl methylene group, an ethylene group and a tetraalkyl ethylene group, more preferably one of a dialkyl methylene group, an ethylene group and a tetraalkyl ethylene group.

The complex represented by Formula (I) is preferably a complex represented by Formula (II). In Formula (II), Z¹ and Z² represent a nitrogen-containing 6-membered aromatic ring of which a nitrogen atom coordinates with platinum. L¹ represents a single bond or a 2- valence connection group. L¹ is the same with that of Formula (I), and a preferable range thereof is also the same. R¹"²¹ and R^P22 represent a hydrogen atom or a substituent group, independently, and the substituent group is the same with those of Substituent group A. R^P21 and R^P22 substituted with the same pyrazole ring may form a condensed ring by means of connection. R^P22 may form a ring by bonding to R^P22 substituted with another pyrazole.

R^P21 is preferably one of a hydrogen atom, a methyl group, a trifluoromethyl group, a t- butyl group, and a cyano group, more preferably one of a methyl group, a trifluoromethyl group, a t-butyl group, and a cyano group, and still more preferably one of a trifluoromethyl group, a t- butyl group, and cyano group.

R^P22 is preferably one of a hydrogen atom, a methyl group, a trifluoromethyl group, a t- butyl group, a cyano group, and groups forming substituted or non-substituted methylene or ethylene by means of connection between R^P22, more preferably one of a hydrogen atom, a cyano group, and groups forming substituted or non-substituted methylene or ethylene by means of connection between R¹"²², still more preferably one of a hydrogen atom and groups forming substituted or non-substituted methylene or ethylene by means of connection between R¹"²², and most preferably a hydrogen atom.

The complex represented by Formula (I) is preferably a complex represented by Formula (III). In Formula (III), Z¹ and Z² represent a nitrogen-containing 6-membered aromatic ring of which a nitrogen atom coordinates with platinum. L¹ represents a single bond or a 2- valence connection group. L¹ is the same with that of Formula (I), and a preferable range thereof is also the same. R^P31, R^P32, and R^P33 represent a hydrogen atom or a substituent group, independently, and the substituent group is the same with those of Substituent group A. R^P31 and R^P32, and R^P32 and R^P33 may form a condensed ring by means of connection therebetween.

Examples of the condensed ring formed by connection between R^P31 and R^P32 and between R^P32 and R^P33 can include a benzene ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, a pyrrole ring, a pyrazole ring, an imidazole ring, an oxazole ring, a thiazole ring, an isothiazole ring, and an isooxazole ring. Among them, a benzene ring, a pyridine ring, a pyrimidine ring, and a pyrazine ring are preferable. The rings may be condensed with another ring.

R^P31 is preferably one of a hydrogen atom, an alkyl group, an aryl group, a cyano group, and a group forming a condensed ring with R^P32, more preferably one of a hydrogen atom, a methyl group, a t-butyl group, a phenyl group, a cyano group, a trifluoromethyl group, and a group forming a condensed ring with R^P32, and still more preferably one of a methyl group, a t- butyl group, and a group forming a condensed ring with R^P32.

R^P32 is preferably one of a hydrogen atom, an alkyl group, an aryl group, a cyano group, a group forming a condensed ring with R^P31, and a group forming a condensed ring with R^P33, more preferably one of a hydrogen atom, a methyl group, a t-butyl group, a phenyl group, a cyano group, a trifluoromethyl group, a group forming a condensed ring with R^P31, and a group forming a condensed ring with R^P33, and still more preferably one of a t-butyl group, a cyano group, a trifluoromethyl group, and a group forming a condensed ring with R^P31.

R^P33 is preferably one of a hydrogen atom, an alkyl group, an aryl group, a cyano group, and a group forming a condensed ring with R^P32, more preferably one of a hydrogen atom, a methyl group, and a group forming a condensed ring with R^P32, and still more preferably one of a hydrogen atom and a group forming a condensed ring with R^P32.

The complex represented by Formula (I) is preferably a complex represented by Formula (TV). Formula (TV) is described, hi Formula (IV), Z¹ and Z² represent a nitrogen- containing 6-membered aromatic ring of which a nitrogen atom coordinates with platinum. L¹ represents a single bond or a 2-valence connection group. L¹ is the same with that of Formula (I), and a preferable range thereof is also the same. R^P41 and R^P42 represent a hydrogen atom or a substituent group, independently, and as the substituent group is used the substituent groups selected from the groups of Substituent group A. R^p41 and R^P42 may form a condensed ring by means of connection therebetween. Examples of the condensed ring formed by connection between R^P41 and R^P42 can include a benzene ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, a pyrrole ring, a pyrazole ring, an imidazole ring, an oxazole ring, a thiazole ring, an isothiazole ring, and an isooxazole ring. Among them, a benzene ring, a pyridine ring, a pyrimidine ring, and a pyrazine ring are preferable. The rings may be condensed with another ring.

R^P41 is preferably one of a hydrogen atom, an alkyl group, an aryl group, a cyano group, and a group forming a condensed ring with R^P42, more preferably one of a hydrogen atom, a methyl group, a t-butyl group, a phenyl group, a cyano group, a trifluoromethyl group, and a group forming a condensed ring with R^P42, and still more preferably one of a methyl group, a cyano group, and a group forming a condensed ring with R^P42.

R^P42 is preferably one of a hydrogen atom, an alkyl group, an aryl group, a cyano group, and a group forming a condensed ring with R^P41, more preferably one of a hydrogen atom, a methyl group, a t-butyl group, a phenyl group, a cyano group, a trifluoromethyl group, and a group forming a condensed ring with R^P41, and still more preferably one of a methyl group, a cyano group, and a group forming a condensed ring with R^P41. The complex represented by Formula (II) is preferably a complex represented by Formula (IIA). Formula (HA) is described. In Formula (HA), L¹ represents a single bond or a 2- valence connection group. L¹ is the same with that of Formula (I)₅ and a preferable range thereof is also the same. R^P21, R^P22, R^P51, R^P52, R^P53, R^P54, R^P55, and R^P56 represent a hydrogen atom or a substituent group. R^P21 and R^P22 are the same with those of Formula (E) and preferable ranges thereof are also the same. R^P51 to R^P56 represent a hydrogen atom or a substituent group. The substituent groups represented by R^P51 to R^P56 are the same with those of Substituent group A. R^P51 to R^P5δ may form a condensed ring by means of connection therebetween.

R^P51 and R^P54 are preferably one of a hydrogen atom, an alkyl group, an aryl group, an amino group, an alkoxy group, an aryloxy group, an acyl group, an alkoxycarbonyl group, an alkylthio group, a sulfonyl group, a hydroxyl group, a halogen atom, a cyano group, a nitro group, and a heterocyclic group, more preferably one of a hydrogen atom, an alkyl group, an aryl group, a halogen atom, a cyano group, a nitro group, and a heterocyclic group, still more preferably one of a hydrogen atom, a methyl group, a t-butyl group, a trifluoromethyl group, a phenyl group, a fluorine atom, a cyano group, and a pyridyl group, still more preferably one of a hydrogen atom, a methyl group, and a fluorine atom, and most preferably a hydrogen atom.

R^P53 and R^p56 have the same preferable ranges as those of R^P51 and R^P54

R^P52 and R^P55 are preferably one of a hydrogen atom, an alkyl group, an aryl group, an amino group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, a halogen atom, a cyano group, and a heterocyclic group, more preferably one of a hydrogen atom, an alkyl group, an aryl group, an amino group, an alkoxy group, an aryloxy group, and a heterocyclic group, still more preferably one of a hydrogen atom, a methyl group, a t-butyl group, a dimethyl amino group, a diphenyl amino group, a methoxy group, and a carbazolyl group, and most preferably a hydrogen atom.

The complex represented by Formula (IIA) is preferably a complex represented by Formula (IIB). Formula (HB) is described. In Formula (UB), R^P21, R^P22, R^P51, R^P52, R^p53, R^P54, R^P55, R^P56, R^Pδl, and R^P62 represent a hydrogen atom or a substituent group. R^P21 and R^P22 are the same with those of Formula (II) and preferable ranges thereof are also the same. R^P51 to R^P5δ are the same with those of Formula (DA) and preferable ranges thereof are also the same. R^P61 and R^P62 represent a hydrogen atom or a substituent group. The substituent groups represented by R^Pδl and R^Pδ2 are the same with those of Substituent group A. R^Pδl and R^Pδ2 are preferably one of a hydrogen atom, an alkyl group, an aryl group, a halogen atom, a cyano group, and a heterocyclic group, more preferably one of a hydrogen atom, a methyl group, a trifluoromethyl group, a phenyl group, a fluorine atom, a cyano group, and a pyridyl group, still more preferably one of a methyl group, a phenyl group, and a pyridyl group, and most preferably a methyl group. The complex represented by Formula (ElB) is preferably a complex represented by Formula (IIC). Formula (IIC) is described. In Formula (HC), R^P21, R^P22, R^P51, R^P52, R^P53, R^P54 ₅ R^P55, and R^P5S represent a hydrogen atom or a substituent group. R^P21 and R^P22 are the same with those of Formula (II) and preferable ranges thereof are also the same. R^P51 to R^P56 are the same with those of Formula (ILA) and preferable ranges thereof are also the same.

The complex represented by Formula (IIC) is preferably a complex represented by Formula (IID). Formula (ItD) is described. In Formula (HD), R^P51, R^P52, R^P53, R^P54, R^P55, and R^P56 represent a hydrogen atom or a substituent group. R^P21 is a substituent group. R^P51 to R^P56 are the same with those of Formula (DA) and preferable ranges thereof are also the same. R^P23 are the same with those of Substituent group A. R^P21 is preferably one of an alkyl group, an aryl group, an amino group, an alkoxy group, an aryloxy group, an acyl group, an alkoxycarbonyl group, an alkylthio group, a sulfonyl group, a hydroxyl group, a halogen atom, a cyano group, a nitro group, and a heterocyclic group, more preferably one of an alkyl group, an aryl group, a sulfonyl group, a halogen atom, a cyano group and a heterocyclic group, still more preferably one of a alkyl group, a perfluoroalkyl group, an aryl group, a perfiuoroaryl group, a sulfonyl group, a halogen atom, a cyano group, and a heterocyclic group, still more preferably one of a methyl group, a t-butyl group, a trifluoromethyl group, a phenyl group, a tolyl group, a pentafluorophenyl group, a mesyl group, a tosyl group, a fluorine atom, a cyano group, and a pyridyl group, still more preferably one of a methyl group, a t-butyl group, a trifluoromethyl group, and a cyano group, and still more preferably one of a t-butyl group, a trifluoromethyl group, and a cyano group.

In Formula (HD), R^P51, R^P53, R^P54, and R^P56 are all preferably a hydrogen atom.

Examples of the platinum complex which can be used for the electroluminescent device according to the present invention can include Compounds (1) to (6), Compounds (12) to (97), Compounds (138) to (140), Compounds (144) to (152), and Compounds (178) to (242) described in International Publication No. WO 2004/108859. Examples of compounds are further described below, but the present invention is not limited to the examples.

P-7 P-8 P-9

P-31 P-32 P-33

P-67 P-68 P-6

P-103 P-104 P-105

P-106 P-107 P-108

P-124 P-125 P-126

P-130 P-131 P-132

P-133 P-134 P-135

P-136 P-137 P-138

P-139 P-140 P-141

P-142 P-143 P-144

P-145 P-146 P-147

P-148 P-149 P-150

P-154 P-155 P-156

P-160 P-161 P-162

P-166 P-167 P-168

P- 169 P-170 P-171

P- 172 P-173 P-174

P-175 P-176 P-177

P-211 P-212 P-213

P-217 P-218 P-219

P-220 P-221 P-222

P-225 P-226 P-227

P-228 P-229 P-230

P-231 P-232 P-233

P-234 P-235 P-236

P-237 P-238 P-239

P-243 P-244 P-245

P-246 P-247 P-248

P

P

The ionization potential of the host material contained in the light emitting layer is preferably in the range of 5.8 eV to 6.3 eV, more preferably in the range of 5.95 eV to 6.25 eV, and most preferably in the range of 6.0 eV to 6.2 eV.

The electron mobility of the host material contained in the light emitting layer is preferably in the range of 1 x 10^"6 cmVVs to 1 x 10^"1 cm²/Vs, more preferably in the range of 5 x 10^'6 cmVVs to 1 x 10^'2 ciwVVs, still more preferably in the range of 1 x 10^"5 cm²/Vs to 1 x 10^"2 cmVVs, and most preferably in the range of 5 x 10^"5 cm²/Vs to 1 x 10^"2 cmVVs .

The hole mobility of the host material contained in the light emitting layer is preferably in the range of 1 x 10^"6 cm^z/Vs to 1 x 10^"1 cmVVs, more preferably in the range of 5 x 10^"6 crnVVs to 1 x 10^"2 cm²/Vs, still more preferably in the range of 1 x 10^"5 cnrVVs to 1 x 10^~2 cm²/Vs, and most preferably in the range of 5 x 10^"5 cm²/Vs to 1 x 10^~2 cmYVs .

The glass transition point of the host material, the electron transporting material and the hole transporting material contained in the light emitting layer is preferably in the range of 9O⁰C to 400⁰C₃ more preferably in the range of 100⁰C to 380⁰C, still more preferably in the range of 12O⁰C to 370⁰C₃ and most preferably in the range of 140⁰C to 360⁰C.

In the organic electroluminescent device according to the present invention, the maximum wavelength of the emitted light is preferably in the range of 390nm to 495nm in view of blue color purity and more preferably in the range of 400nm to 490nm. The light emitting device according to the present invention may have the maximum wavelength of the emitted light in the range of 500nm and more and may be a white light emitting device.

In the organic electroluminescent device according to the present invention, the x value of CBE chromaticity of the emitted light is preferably 0.22 or less in view of the blue color purity and more preferably 0.20 or less.

In the organic electroluminescent device according to the present invention, the y value of CIE chromaticity of the emitted light is preferably in the range of 0.25 or less, more preferably 0.20 or less, and most preferably 0.15 or less.

In the organic electroluminescent device according to the present invention, the half width of an emission spectrum is preferably lOOnm or less, more preferably is 90nm or less, still more preferably 80ntn or less, and most preferably 70nm or less.

The Ti level (energy level of the least triplet excited state) of the phosphorescent material (the compounds according to the present invention and/or phosphorescent material used therewith) which can be used in the present invention is preferably in the range of 60 Kcal/mol (251.4 KJ/mol) to 90 Kcal/mol (377.1 KJ/mol), more preferably in the range of 62 Kcal/mol (259.78 KJ/mol) to 85 Kcal/mol (356.15 KJ/mol), and most preferably in the range of 65 Kcal/mol (272.35 KJ/mol) to 80 Kcal/mol (335.2 KJ/mol).

The Ti level (energy level of the least triplet excited state) of the host material contained in the light emitting layer is preferably in the range of 60 Kcal/mol (251.4 KJ/mol) to 90 Kcal/mol (377.1 KJ/mol), more preferably in the range of 62 Kcal/mol (259.78 KJ/mol) to 85 Kcal/mol (356.15 KJ/mol), and most preferably in the range of 65 Kcal/mol (272.35 KJ/mol) to 80 Kcal/αxol (335.2 KJ/mol).

The Ti level (energy level of the least triplet excited state) of the layer (such as the hole transporting layer, the electron transporting layer, the charge blocking layer, and the exciter blocking layer) adjacent to the light emitting layer is preferably in the range of 60 Kcal/mol (251.4 KJ/mol) to 90 Kcal/mol (377.1 KJ/mol), more preferably in the range of 62 Kcal/mol (259.78 KJ/mol) to 85 Kcal/mol (356.15 KJ/mol), and most preferably in the range of 65 Kcal/mol (272.35 KJ/mol) to 80 Kcal/mol (335.2 KJ/mol).

In the organic electroluminescent device according to the present invention, the light extraction efficiency can be improved by a variety of known techniques. For example, by processing the surface shape of a substrate (for example, forming a micro uneven pattern), or controlling the refractive indexes of the substrate, the ITO layer, and the organic layer, or controlling the thickness of the substrate, the ITO layer, and the organic layer, the light extraction efficiency can be improved, thereby enhancing the external quantum efficiency.

The organic electroluminescent device according to the present invention may be of a so- called top emission type which extracts the light from the positive electrode (see Japanese Unexamined Patent Application Publication Nos. 2003-208109, 2003-248441, 2003-257651, anxl 2003-282261).

The material of the substrate used in the organic electroluminescent device according to the present invention is not particularly limited, and examples thereof can include an inorganic material such as zirconia-stabilized yttrium and glass, poly ester such as poly ethyleneterephthalate, poly butylene terephthalate, and poly ethylene naphthalate, a high-molecular material such as poly ethylene, poly carbonate, poly ethersulfone, poly arylate, aryldiglycolcarbonate, poly imide, poly cycloolefin, norbornene resin, poly (chlorotrifluoro ethylene), Teflon (registered trademark), and poly tetrafluoro ethylene-poly ethylene copolymer.

The organic electroluminescent device according to the present invention may contain a blue fluorescent compound. Alternatively, a multi-color light emitting device and a full color ligtrt emitting device may be manufactured by using a blue light emitting device containing a blue fluorescent compound and the light emitting device according to the present invention together.

In the organic electroluminescent device according to the present invention, the host material contained in the light emitting layer may be a kind or two kinds or more.

The organic electroluminescent device according to the present invention includes preferably a plurality of host materials in the light emitting layer in order to control the transport property of the hole and electron in the light emitting layer. As a plurality of host materials, a hole transporting host material excel in the hole transport property (hole transporting host) and an electron transporting host material excel in the electron transport property (electron transporting host) can be used in combination. Here, "excel in the hole transport property" or "excel in tire electron transport property" indicates the relative relationship of a plurality of the host materials used in combination, and indicates that one of the plurality of the host materials is superior to another in the hole transport property or the electron transport property.

When a compound according to the present invention is used as the host material in a, light emitting layer, and when a compound according to the present invention is superior in the electron transport property, the compound can be used in combination with a host material excel in the hole transport property. And when a compound according to the present invention is superior inttie hole transport property, the compound can be used in combination with a host material excel in the electron transport property. -Hole transporting host- As a hole transporting host used in a light emitting layer according to the present invention, publicly known hole transporting materials can be used. For example, the following materials can be exemplified; pyrrole, carbazole, triazole, oxazole, oxadiazole, imidazole, polyarylalkane, pyrazoline, pyrazolone, phenylenediamine, arylamine, amino substituted chalkone, styryl anthracene, fluorenone, hydrazine, stilbene, silazane, aromatic tertiary amine compound, styryl amine compound, aromatic dimethylidene compound, porphyrin compound, polysilane compound, poly(N-vinylcarbazole), aniline copolymer, thiophene oligomer, conductive polymer oligomer such as polythiophene, organic silane, carbon film, and their derivatives. Among them, carbazole derivative, aromatic tertiary amine compound, thiophene derivative are preferred, particularly, those having a plurality of carbazole skeletons and/or aromatic tertiary amine akeltones in their molecules are preferred. -Electron transporting host- As an electron transporting host used in a light emitting layer according to the present invention, publicly known electron transporting materials can be used. For example, the following materials can be exemplified; pyridine, pyrimidine, triazine, imidazole, triazole, oxazole, oxadiazole, fluoreneone, anthraquinodimethane, anthrone, diphenylquinone, thiopyrandioxide-, carbodiimide, fluorenylidene methane, distyryl pyradine, fluorine substituted aromatic compound, heterocyclic tetracarboxylic acid anhydride such as naphthaleneperylene, phthalocyanine, ancl their derivatives (which may form a condensed ring with other ring) and a variety of metal complerxes represented by a metal complex of 8-quinolinol derivative, metal phthalocyanine or a metal salt which has benzoxazole or benzothiazole as ligand.

An electron transporting host is preferably metal complex, azole derivative (benzimidazole derivative, imidazopyridine derivative), azine derivative (pyridine derivative, pyrimidine derivative, triazine derivative). Among them, with respect to the durability, metal complex is preferred in the present invention. A metal complex has a ligand containing at least one of nitrogen atom, oxygen atom and sulfur atom coordinating with a metal. A metal ion in a metal complex is not especially limited, but preferably beryllium ion, magnesium ion, aluminium ion, gallium ion, zinc ion, indium ion or tin ion, more preferably beryllium ion, aluminium ion, gallium ion or zinc ion, still more preferably aluminium ion or zinc ion.

The organic electroluminescent device according to the present invention has preferably a layer containing a compound with an ionization potential of 5.9 eV or more (more preferably 6.0 eV or more) between the negative electrode and the light emitting layer, and more preferably the electron transporting layer with an. ionization potential of 5.9 eV or more.

The method of forming the organic layer containing the compounds according to the present invention is not particularly limited, and examples thereof can include a resistance heating deposition method, an electron beam method, a sputtering method, a molecule deposition method, a coating method (such as a spray coating method, a dip coating method, an impregnation method, a. roll coating method, a gravure coating method, a reverse coating method, a roll brush method, an air knife coating method, a curtain coating method, a spin coating method, a flow coating method, a bar coating method, a micro gravure coating method, an air doctor coating method, a blade coating method, a squeeze coating method, a transfer roll coating method, a kiss coating method, a. cast coating method, an extrusion coating method, a wire-bar coating method, and a screen coating method), an inkjet method, a printing method, an LB method, and a transfer method. Among them, the resistance heating deposition method, the coating method, and the transfer method are more preferable in view of characteristics and manufacturing thereof. The layer containing the compounds according to the present invention is formed on a substrate by the use of any one method described above, but the thickness thereof is not particularly limited. The thickness is preferably IOnm or more and more preferably in the range of 50nm to 5μm.

The concentration of the transition metal complex contained in the light emitting layer is not particularly limited, but is preferably equal to or less than that of the host material which is a main component thereof, more preferably in the range of 0.1 mass% to 50 mass%, still more preferably in the range of 0.2 mass% to 30 mass%, still more preferably in the range of 0.3 mass%E> to 20 mass%, and most preferably in the range of 0.5 mass% to 10 mass%. (In this specification, mass ratio is equal to weight ratio.)

The positive electrodes serves to supply holes to the hole injecting layer, the hole transporting layer, and the light emitting layer, and may be made of metal, alloy, metal oxide, electrical conductive compound, or mixtures thereof. Among them, the material having a work function of 4 eV or more is preferable. Specific examples of the material can include conductive metal oxide such as tin oxide, zinc oxide, indium oxide, and indium-tin oxide (ITO), metal such as gold, silver, chromium, and nickel, a mixture or stacked material of the metal and the conductive metal oxide, an inorganic conductive material such as copper iodide and copper sulfide, an organic conductive material such as poly aniline, poly thiophene, and poly pyrrole, and a stacked material of the materials and ITO. The conductive metal oxide is preferable and ITO is more preferable in view of productivity, high conductivity, an.d transparency. The thickness of the positive electrode can be properly selected depending upon tfcie materials, but is preferably in the range of lOnm to 5 urn, more preferably in the range of 50nm to lμm, and most preferably in the range of lOOnm to 500nm.

The positive electrode is generally used in the state that it is formed on a soda lime glass substrate, an alkali-free glass substrate, a transparent resin substrate, or the like. When a glass substrate is used, the material thereof is preferably the alkali-free glass so as to reduce the ions eluted from the glass. When the soda lime glass substrate is used, it is preferable that a barrier coating process with silica is performed thereto. The thickness of the substrate is not particularly limited so long as it is enough to maintain the mechanical strength thereof, but when the glass substrate is used, the thickness of the substrate is preferably 0.2mm or more and more preferably 0.7mm or more.

A variety of methods can be used to manufacture the positive electrode. For example, when the positive electrode is made of ITO, the positive electrode is formed as a film by the use of an electron beam method, a sputtering method, a resistance heating deposition method, a chemical reaction method )a sol-gel method), or a method of coating a material in which indium-tin oxide is dispersed.

By performing a cleaning process or other processes to the positive electrode, the driving voltage of the device can be decreased or tiie light emission efficiency thereof can be increased. For example, when the positive electrode is made of ITO, UV-ozone processing or plasma processing is advantageous.

The negative electrode serves to supply electrons to the electron injecting layer, the electron transporting layer, and the light emitting layer, and the material of the negative electrode is selected in consideration of the adhesion, to a layer contacting the negative electrode, such as the electron injecting layer, the electron transporting layer, and the light emitting layer, the ionization potential, and the stability. Examples of th.e material of the negative electrode can include metal, alloy, metal halide, metal oxide, conductive compounds, and mixtures thereof. The specific examples of the material can include alkali metal (such as Li, Na, and K) and fluoride or oxide thereof, alkali earth metal (such as Mg and Ca) and fluoride or oxide thereof, gold, silver, plumbum, aluminum, sodium-potassium alloy or mixture, lithium-aluminum alloy or mixture, magnesium-silver alloy or mixture, and rare earth metal such as indium and yttrium. Among them, the materials having a work function of 4 eV or less are preferable, and aluminum, lithium- aluminum alloy or mixture, and magnesium-silver alloy or mixture are more preferable. The negative electrode may have a single-layered structure of the compound and the mixture described above, or may have a multi-layered structure including the compounds and the mixtures described above. A multi-layered structure such as aluminum/hthium fluoride and aluminum/lithium oxide is preferable. The thickness of the negative electrode can be properly selected depending upon, the materials, but is preferably in the range of IOnm to 5μm, more preferably in the range of 5θ3im to lμm, and most preferably in the range of lOOnm to lμm.

The electron beam method, the sputtering method, the resistance heating deposition method, the coating method, the transfer method, or the like can be used to manufacture the negative electrode. Two or more metals can be simultaneously deposited as simplexes. In addition, an alloy electrode may be formed by simultaneously depositing a plurality of metals and an alloy adjusted in advance may be deposited.

The sheet resistances of the positive electrode and the negative electrode are prefera-tly low and more preferably several hundreds or less Ω/D.

The light emitting layer may be made of any material as long as it has a function of injecting holes from the positive electrode, the hole injecting layer, or the hole transporting layer at the time of application of a voltage and injecting electrons from the negative electrode, the electron injecting layer, or the electron transporting layer, a function of moving the injected charge carriers, or a function of providing a place for re-coupling the holes and the electrons to emit light. Examples of the material for the light emitting layer can include a variety of metal complexes such as a rare earth complex or a metal complex of benzooxazole, benzoimidazole, benzothiazole=₃ styrylbenzene, polyphenyl, diphenyl butadiene, tetraphenyl butadiene, naphthalimide, coumaLrin, perylene, perignon, oxadiazole, aldazine, pyrazine, cyclopentadiene, bisstyrylanthracene, quinacridone, pyrrolopyridine, thiadiazoropyridine, styrylamine, aromatic dimethylidine compound, and 8-quinolinol, polymer compounds such as poly thiophene, poly phenylene, aaid poly phenylene vinylene, transition metal complexes such as organic silane, iridium trisphenylpyridine complexes, and platinum forpyrine complexes, and derivatives thereof.

The light emitting material contained in a light emitting layer may be a single or two or more kinds different from each other.

The thickness of the light emitting layer is not particularly limited, but is preferably in the range of lnm to 5μm, more preferably in the range of 5nm to lμm, and most preferably in tfcie range of IOnm to 500nm.

The method of forming the light emitting layer is not particularly limited, but is preferably one of the resistance heating deposition method, the electron beam method, the sputtering method, the molecule deposition method, the coating method, the inkjet method, the printing method, "the LB method, and the transfer method, and more preferably one of the resistance heating deposition method and the coating method.

The light emitting layer may be made of a single compound, or may be made of a plurality of compounds. The light emitting layer may have a single layer or a plurality of layers. In this case, the respective layers may emit light of different colors to emit, for example, white light. The single-layered light emitting layer may emit the white light. When the light emitting layer includes a plurality of layers, the respective layers may be made of a single compound or may be made of a plurality of compounds.

Further, in order to enhance the light emitting efficiency and improve the durability, the same light emitting materials as contained in a light emitting material can be preferably contained in a layer adjacent to the positive electrode side of the light emitting layer or a layer adjacent to the negative electrode side of the light emitting layer. Thereby, it is assumed that the charges retained in the positive electrode side's interface or the negative electrode side's interface of a light emitting layer can be effectively used for light emitting. hi addition, the present invention can employ a constitution where an energy transfer from triplet exciton to singlet exciton is used. For example, as described in JPA-2005-190949, a light emitting layer may contain a compound that emits fluorescence when a voltage is applied and a compound that has a function of amplifying a light emitting intensity during the application of a voltage by increasing the number of singlet exciton generated during the application of a voltage.

The materials of the hole injecting layer and the hole transporting layer may have any one of a function of injecting holes from the positive electrode, a function of transporting holes, and a function of blocking electrons injected from the negative electrode. Specific examples thereof can include a conductive high-molecular oligomer such as carbazole, triazole, oxazole, oxadiazole, imidazole, poly arylalkane, pyrazoline, pyrazolone, phenylenediamine, arylamine, amino- substibuted chalcone, styrylanthracene, fluorenone, hydrazone, stilbene, silazane, aromatic third- degree amine compound, styryl amine compound, aromatic JIMECHIRI DIN compound, porphyrin compound, poly silane compound, poly(N-vinylcarbazole), aniline copolymer, thiophene oligomer, and poly thiophene, an organic silane, a carbon film, the compounds according to the present invention, and derivatives thereof. The thickness of the hole injecting layer is not particularly limited, but is preferably in the range of lnm to 5μm, more preferably in the range of lnm to lOOnm, and most preferably in the range of lnm to lOnm. The thickness of the hole transporting layer is not particularly limited, but is preferably in the range of lnm to 5μm, more preferably in the range of 5nm to 1 μm, and most preferably in the range of lOnm to 500nm. The hole injecting layer and the hole transporting layer may have a single-layered structure including one or two or more kinds of the above-mentioned materials, or may have a multi-layered structure including a plurality of layers with a composition of like or different kinds.

When the hole injecting layer and the hole transporting layer are multi-layered structures, assuming that an ionization potential of a light emitting layer is IpO, of the hole injecting layer and the hole transporting layer, an ionization potential of a layer adjacent to a light emitting layer is IpI, an ionization potential of a layer located in n-th position, from a light emitting layer side is Ipn, the relation represented by the following numeral formula (1) is preferably satisfied with respect to the low-voltage driving. Numeral formula (1): IpO > IpI > Ip2 >— > Ipn-1 > Ipn (n represents an integer of 2 or more.)

In the hole injecting layer and the hole transporting layer of an organic EL device according to the present invention, an electron receptive dopant can be contained. As an electron receptive dopant introduced into the hole injecting layer or tke hole transporting layer, inorganic compounds or organic compounds may be used as long as they are electron receptive and have a property of oxidizing an organic compound.

In particular, inorganic compounds include metal halide, such as ferric chloride, aluminum chloride, gallium chloride, indium chloride and antimony perrtachloride, and metal oxide, such as vanadium pentoxide, molybdic anhydride.

When the electron receptive dopant is an organic compound, compound having nitro group, halogen, cyano group or trifluoromethyl group etc. as substituent, quinone compound, acid anhydride compound and fullerene can be preferably used.

In addition to the above, compounds described in JP_^A-06-212153, JPA-11-111463, JPA- 11-251067, JPA-2000-196140, JPA-2000-286054, JPA-20O O-315580, JPA-2001-102175, JPA- 2001-160493, JPA-2002-252085, JPA-2002-56985, JPA-2003-157981, JPA-2003-217862, JPA- 2003-229278, JPA-2004-342614, JPA-2005-72012, JPA-2005-166637, JPA-2005-029643 can be preferably used.

These electron receptive dopants can be used solely or in two or more kinds. Amount of the electron receptive dopant varies with the type of materials, however it is preferably 0.01 mass% to 50 mass%, more preferably 0.05 mass% to 2 O mass%, particularly more preferably 0.1 mass% to 10 mass% with respect to the hole transporting layer materials. The vacuum deposition method, the LB method, the coating method using the material of the hole injecting layer and the hole transporting layer dissolved or dispersed in. a solvent, the inkjet method, the printing method, or the transfer method can be used to form the hole injecting layer and the hole transporting layer. When the coating method is used, the material can be dissolved or dispersed along with a resin component. Examples of the resin component can include poly vinyl chloride, poly carbonate, poly styrene, poly methlymethacrylate, poly fcmtylmethacrylate, poly ester, poly sulfon, poly phenyleneoxide, poly butadiene, poly (N-vinylcaarbazole), hydrocarbon resin, ketone resin, phenoxy resin, poly amide, ethyl cellulose, vinyl acetate, ABS resin, poly urethane, melamine resin, unsaturated polyester resin, alkyd resin, epoxy resin, and silicon resin.

The materials for the electron injecting layer and the electron transporting layer may have any one of a function of injecting electrons from the negative electrode, a function of transporting electrons, and a function of blocking holes injected from the positive electrode. Specific examples thereof can include a variety of metal complexes such as metal complexes of aromatic tetracarbonic acid anhydride such as triazole, oxazole, oxadiazole, imidazole-, fluorenone, anthraquinodimethane, anthrone, diphenyl quinone, thiopyrandioxide, carbodimide, fluorenyhdene methane, distyrylpyrazine, naphthalene, and perylene, metal complexes of ptthalocyanine and 8- quinolinol, and metal complexes having metal phthalocyanine, benzooxazole., or benzothiazole as a ligand, organic silane, and derivatives thereof. The thickness of the electron injecting layer and the electron transporting layer are not particularly limited, but are preferably in the range of lnm to 5μm, more preferably in the range of 5nm to lμm, and most preferably in the range of lOnm to 500nm. The electron injecting layer and the electron transporting layer may liave a single-layered structure including one or two or more kinds of the above-mentioned materials, or may have a multi-layered structure including a plurality of layers with a composition of l±ke or different kinds.

When the electron injecting layer and the electron transporting layer axe multi-layered structures, assuming that an electron affinity of a light emitting layer is EaO, an electron affinity of the electron, transporting layer adjacent to a light emitting layer is EaI, an electron affinity of the electron transporting layer located in n-th position from a light emitting layer side is Earn, the relation represented by the following numeral formula (2) is preferably satisfied with respect to the low-voltage driving. Numeral formula (2): EaO < EaI < Ea2 <^•••< Eam-1 < Earn (m represents an integer of 2 or more.)

The electron injecting layer or the electron transporting layer of an oxganic EL device according to the present invention, an electron donating dopant can be contained. As an electron donating dopant introduced into the electron injecting layer or the electron transporting layer, those having properties of electron donating ability and reducing organic compounds can be used. For example, aLkaline metals such as Li, alkali earth metals such as Mg, transition metals including rare earth metals, and reductive organic compounds, etc are preferably used. As -the metals, metals which have work function of 4.2eV or below are preferable, in particular Li, ^"Na, K, Be, Mg, Ca, Sr, Ba, Y, Cs, La, Sm, Gd and Yb, etc are exemplified. As the reductive organic compounds, nitrogen-containing compound, sulfur-containing compound and phosphor-containing compound are exemplified.

In addition to the above, materials described in JPA-06-212153, JPA^-2000-196140, JPA- 2003-68468, JPA-2003-229278, JPA-2004-342614, etc. can be preferably u_sed.

These electron donating dopants can be used solely or in two or more kinds.

Amount of the electron donating dopant varies with the type of materials, however it is preferably 0.01 mass% to 99 mass%, more preferably 1.0 mass% to 80 mass%, particularly more preferably 2.0 mass% to 70 mass% with respect to the electron transporting layer materials. The vacuum deposition method, the LB method, the coating method using the material of the electron injecting layer and the electron transporting layer dissolved or dispersed in a solvent, the inkjet method, the printing method, or the transfer method can be used to form the electron injecting layer and the electron transporting layer. When the coating method is used, the material can be dissolved or dispersed along with a resin component. Examples of the resin componeπet can include the materials exemplified for the hole injecting layer and the hole transporting layer.

A material of the protective layer may have a function of preventing a material of promoting device deterioration such as moisture and oxygen from entering the device. Specific examples thereof can include metal such as In, Sn, Pb, Au, Cu, Ag, Al, Ti, and Ni, metal oxide such as MgO, SiO, SiO₂, Al₂O₃, GeO, NiO, CaO, BaO, Fe₂O₃, Y₂O₃, and TiO₂, metal fluoride such as MgF₂, LiF, AlF₃, and CaF₂, nitride such as SiN_x and SiO_xN_y, poly ethylene, poly propylene, poly methylrnethacrylate, poly imide, poly urea, poly tetrafluoroethylene, poly chlorotrifluoroehtylene, poly dichlorodifluoroethylene, a copolymer of chlorotrifluoroethylene and dichlorodifluoroethylene, a copolymer obtained by copolymerizing tetrafluoroethylene and monomer mixture including at least one kind of co-monomer, fluorine-containing copolymer having a cyclic structure in a copolymer main chain, a water absorbing material having a water absorption rate of 1% or more, and a moisture-resistant material having a water absorption rate of 0.1% or less. The method of forming the protective layer is not particularly limited, and examples thereof can include the vacuum deposition method, the sputtering method, the reactive spattering method, an MBE (molecular beam epitaxy) method, a cluster ion beam method, an ion plating method, a plasma polymerization method (high-frequency excited ion plating method), a plasma CVD method, a laser CVD method, a thermal CVD method, a gas source CVD method, the coating method, the printing method, and the transfer method.

La an organic EL device according to the present invention, a charge generating layer may be provided between a plurality of light emitting layers in order to enhance the light emitting efficiency.

The charge generating layer has a function of generating charges (hole and electron) during the application of a voltage, in addition, it has a function of injecting the generated charges into a layer adjacent to the charge generating layer.

Any materials can be used for the material which forms the charge generating layer as long as they have above mentioned functions. The material may be formed by single compound or a plurality of compounds. In particular, those having conductive property, those having semi- conductive property as a doped organic layer or those having electrical insulating property may be used. Materials described in JPA-11-329748, JPA-2003-272860 or JPA-2004-39617 are exemplified.

In more particular, transparent conductive material such as ITO or IZO (indium zin oxxide), organic conductive material such as fullerene, for example C60, or oligo thiopherie, organic conductive material such as metal phthalocyanin, non-metal phthalocyanin, metal porphyrin or non-metal porphyrin, metal material such as Ca, Ag, Al, alloy of Mg: Ag, alloy of Al:Li or alloy of Mg:Li, hole conductive material, electron conductive material and mixture thereof can be used.

As the hole conductive material, for example, hole transporting organic material such as 2- TNATA or NPD in which oxidizing agent having electron extracting property such as F4-TCNQ, TCNQ, FeCL₃ is doped, P-type conductive polymer or P-type semiconductor are exemplified. As the electron conductive material, electron transporting organic material in which metal or metal compound having a work function of less than 4.OeV is doped, N-type conductive polymer or N- type semiconductor are exemplified. N-type semiconductor includes N-type Si, N-type Cds and N- type Zns etc. and P-type semiconductor includes P-type Si, P-type CdTe and P-type Cuo etc. Electrical insulating materials such as V₂O₅ can be used as the charge generating; layer.

The cliarge generating layer may be single layer or a plurality of laminated layers. As constitutions of a plurality of laminated layers, a constitution in which a material having conductive property such as transparent conductive material and metal material, and a hole conductive material or a electron conductive material are laminated, and a constitution in which the hole conductive material and the electron conductive material are laminated are exemplified.

The thickness and materials of the charge generating layer are preferably selected whereby the charge generating layer has 50% or more transmittance of visible light in general. The thickness thereof is not especially limited, but it is preferably 0.5 to 200nm, more preferably 1 to lOOnm, still more preferably 3 to 50nm and particularly more preferably 5 to 30nm.

The method for forming a charge generating layer is not especially limited. The above mentioned method for forming an organic compound layer can be employed.

Although the charge generating layer is constituted between the two or imore layers of light emitting layers, a cathode and an anode side of the charge generating layer may include materials which have a function of injecting charges into layers adjacent to the charge generating layer.

In order to enhance the injection property of electrons into the layer adjacent to the cathode side, it is preferred that electron injecting compounds, such as BaO, SrO, Li₂O, LiCl, LiF, MgF₂, MgO and CaP₂ are laminated on the cathode side of the charge generating layer.

Li addition to the content described above, it is possible to select materials for the charge generating layer, based on the descriptions of JPA-2003-45676, US Patent No.6337492, US Patent No.6107734 and US Patent No.6872472 etc.

The applications of the organic electroluminescent device according to trαe present invention are not particularly limited, but it may be used very suitably in the fields such as display devices, displays, backlights, electronic photographs, lighting light sources, recorrding light sources, exposing light sources, reading light sources, signboards, interiors, optical communications. The compounds according to the present invention represented by ForEtmlas (1) to (5) can be used for medical applications, fluorescent brightening agents, photograph materials, UV absorbing materials, laser pigments, recording medium materials, inkjet pigments, color filter pigments, color-changing filters, and the like.

Example

Hereinafter, embodiments of the present invention will be described, but the present invention is not limited to the embodiments described below. Synthesis of Compound (184)

Imidazolium salt-1 Compound (184)

In the flow of nitrogen, potassium hexamethyldisilazid (1.55g; 7.4 mmol) was added to a toluene (200ml) suspended liquid of imidazolium salt-1 (2.64g; 7.4 mmol), iridium (I) cfcrnloride 1, and 5-cyclooctadiene complex dimer (0.62g; 0.92 mmol) at a room temperature, and the mixture solution was heated and stirred in reflux for 15 hours. Then, the mixture solution was cooled to the room temperature. Thereafter, the solvent was removed by evaporation and the residue was refined by the use of silica gel column chromatography (hexane/chloroform = 1/1), obtaining pcrwders. The obtained powders were melted in chloroform and hexane was added thereto for crystallization, thereby obtaining Compound (184) of 1.17g. The yield was 64%. Here, ¹H-NMR(CDCl₃) 300MHz : δ 8.11 (d, 3H), 7.92 (d, 3H), 7.20 - 7.30 (m, 6H), 7.09 (dd, 3H), 6.98 (dd, 3H-), 6.66 - 6.78 (m, 9H), 6.53 (d, 3H), 6.40 (d, 3H), 6.20 - 6.30 (m, 6H). Synthesis of Compound (185)

Imidazolium salt-2 fac-body/mer-body mixture fac-body Compound (185) In the flow of nitrogen, potassium hexamethyldisilazid (2.5Og; 11.9 mtnol) was added to a xylene (300ml) suspended liquid of imidazolium salt-2 (4.0Og; 11.9 mmol), indium (I) chloride 1, and 5 -cyclooctadiene complex dimer (l.l lg; 1.65 mmol) at a room temperature, and the mixture solution was heated and stirred in reflux for 6 hours. Then, the mixture solution was cooled to the room temperature. Thereafter, the solvent was removed by evaporation, and the residue was refined by the use of silica gel column chromatography (hexane/chloroform = 1/1), obtaining powders of 1.16g. The obtained powders of 0.84g were added to glycerol (10ml) and were stirred in the reflux of nitrogen for 10 hours. After cooling to the room temperature, methanol (30nύL) was added to the reaction solution and powders were extracted therefrom and filtered. The powdecrs were melted in chloroform and hexane was added thereto for crystallization, thereby obtaining Compound (185) of 0.77g. The yield was 29%. Here, ¹H-NMR(CDCl₃) 300MHz : δ 8.13 (A, 3H), 7.86 (d, 3H), 7.11 - 7.35 (m, 9H), 7.07 (dd, 3H), 6.73 (dd, 3H), 6.64 (d, 3H), 3.27 (s, 9H). Synthesis of Compound (208)

Imidazolium salt-1 Compound (208)

In the flow of nitrogen, potassium hexamethyldisilazid (3.84g; 18.3 mmol) was added, to a mesitylene (200ml) suspended liquid of imidazolium salt-1 (6.55g; 18.3 mmol), indium (I) chloride 1, and 5 -cyclooctadiene complex dimer (LOOg; 2.02 mmol) at a room temperature, acid the mixture solution was heated and stirred in reflux for 15 hours. Then, the mixture solution wa-s cooled to the room temperature. Thereafter, the solvent was removed by evaporation, and th& residue was refined by the use of silica gel column chromatography (hexane/chloroform = 1/1 ), obtaining Compound (208) of 1.04g as solid. The yield was 29%. Here, ¹H-ISIMR(CDCl₃) 300MHz : δ 8.12 (d, 3H), 7.92 (d, 3H), 7.20 - 7.30 (m, 6H), 6.97 - 7.12 (m, 6H)₅ 6.65 - 6.81 (m, 9H), 6.44 - 6.53 (m, 6H), 6.19 - 6.30 (m, 6H). [Comparative Example 1]

A cleaned ITO substrate is placed into a vapor deposition apparatus and is coated with copper phthalocyanine with a thickness of lOnm. NPD(N,N'-di-α-naphthyl-N,N'-diphenyl- benzidine) is deposited thereon with a thickness of 40nm. Ir(ppy)₃ and CBP(4,4-N,N' dicarbazole- biphenyl) are deposited on the resultant structure with a ratio (mass ratio) of 5:95 with a thickness of 30nm. BAIq is deposited thereon with a thickness of lOnm, and then AIq (tris(8- hydroxyquinoline) aluminum complex) is deposited thereon with a thickness of 30nm. Thereafter, by installing a patterned mask (light-emitting area of 4mmx5mm) on the resultant organic thin film, depositing lithium fluoride thereon with a thickness of 3nm, and then depositing aluminum thereon with a thickness of lOOnm, an EL device is manufactured. As a result of applying a DC steady voltage to the EL device to emit light by the use of Source Measure Unit 2400 made by Toyo Corporation, the green light could be obtained.

•r(ppy)₃

[Example 1]

By using Compound (1) according to the present invention instead of Ir(ppy)₃ in the light emitting device according to Comparative Example 1, a device is manufactured similarly to Comparative Example 1. The resultant device could be decreased to a half in the number of dark; spots generated in comparison with the device according to Comparative Example 1, thereby reducing the driving voltage for allowing current of 1 mA to flow in the EL device. [Example 2]

By using Ir(ppy)₃, CBP(4,4-N,N' dicarbazole-biphenyl), and Compound (113) according to the present invention with a ratio (mass ratio) of 5:70:25, instead of Ir(ppy)₃ and CBP(4,4-N,N' dicarbazole-biphenyl) in the light emitting device according to Comparative Example 1, a device ds manufactured similarly to Comparative Example 1. The resultant device could be decreased to a. half in the number of dark spots generated in comparison with the device according to ComparatrΛre Example 1, thereby reducing the driving voltage for allowing current of 1 mA to flow in the EL device. [Example 3] By using Ir(ppy)₃ and Compound (184) according to the present invention with a ratio (mass ratio) of 1:2, instead of Ir(ppy)₃ and CBP(4,4-N,N' dicarbazole-biphenyl) in the light emitting device according to Comparative Example 1, a device is manufactured similarly to Comparative Example 1. The resultant device could be decreased to a half in the number of dark spots generated in comparison with the device according to Comparative Example 1, thereby reducing the driving voltage for allowing current of 1 mA to flow in the EL device. [Comparative Example A-O]

A cleaned ITO substrate was placed into a vapor deposition apparatus and NPD ((N,N'-di- α-naphthyl-N,N'-diphenyl)-benzidine) was deposited thereon as a hole transporting layer with a thickness of lOnm. Ir(ppy)₃ as a light emitting material and CBP (4,4-N,N'-dicarbazolbiphenyl) as a host material were deposited on the resultant structure at a ratio (mass ratio) of 5:95 with a thickness of 30nm and BAIq was deposited thereon as an electron transporting layer with a thickness of 40nm. Thereafter, a patterned mask (of which the light emitting area is 4mmx5mm) was placed on the obtained organic thin film, lithium fluoride was deposited thereon with a thickness of about lnm, and then aluminum was co-deposited thereon with a thickness of lOOnm, thereby manufacturing an EL device. As a result of applying a DC steady voltage to the EL device to emit light by the use of Source measure unit 2400 made by Toyo Corporation, green light resulting from Ir(ppy)₃ could be obtained. An EL external quantum yield calculated from the driving voltage and the front brightness of the EL device at 2000cd/m² is shown in Table 1.

2-TNATA

BAIq

[Example A-I] By using Compound (5) according to the present invention instead of the hole transporting layer NPD in the EL device according to Comparative Example A-O, an EL device was manufactured similarly to Comparative Example A-O. An EL external quantum yield calculated from the driving voltage and the front brightness of the EL device at 2000cd/m² is shown in Table 1. [Example A-2]

By using Compound (185) according to the present invention instead of the hole transporting layer NPD in the EL device according to Comparative Example A-O, an EL device was manufactured similarly to Comparative Example A-O. An EL external quantum yield calculated from the driving voltage and the front brightness of the EL device at 2000cd/m² is shown in Table 1. [Example A-3]

By using Compound (208) according to the present invention instead of the hole transporting layer NPD in the EL device according to Comparative Example A-O, an EL device was manufactured similarly to Comparative Example A-O. An EL external quantum yield calculated from the driving voltage and the front brightness of the EL device at 2000cd/m² is shown in Table 1.

Table 1: Driving voltage and EL external quantum yield of the obtained devices at 2000cd/m²

As can be seen apparently from Table 1, the EL devices using the compounds according to the present invention as the hole transporting layer exhibit relatively high light emission efficiency in comparison with the EL device according to the comparative example, and the voltage values with the same brightness are equal to or smaller than that of the EL device according to Comparative Example A-O from the view point of improvement in light emission efficiency. [Comparative Example B-O]

A cleaned ITO substrate was placed into a vapor deposition apparatus, 2-TNATA was deposited thereon as a hole injecting layer with a thickness of 140nm. NPD ((N,N'-di-α-naphthyl- N,N'-diphenyl)-benzidine) was deposited thereon as a hole transporting layer with a thickness of 7nm. Carbazole .derivative (1) was deposited thereon as a hole injection promoting layer with a thickness of 3nm. Firpic as a light emitting material and mCP as a host material were deposited on the resultant structure at a ratio (mass ratio) of 8:92 with a thickness of 30nm and BAIq was deposited thereon as an electron transporting layer with a thickness of 40nm. Thereafter, a patterned mask (of which the light emitting area is 4mmx5mm) was placed on the obtained organic thin film, lithium fluoride was deposited thereon with a thickness of about lnm, and then aluminum was co-deposited thereon with a thickness of lOOnm, thereby manufacturing an EL device. As a result of applying a DC steady voltage to the EL device to emit light by the use of Source measure unit 2400 made by Toyo Corporation, blue-green light resulting from Firpic could be obtained. An EL external quantum yield calculated from the driving voltage and the front brightness of the EL device at 600cd/m² is shown in Table 2.

2-TNATA

Carbazole derivative (1)

[Example B-I]

By using Compound (5) according to the present invention instead of NPD of 7nm as the hole transporting layer in the EL device according to Comparative Example B-O, an EL device was manufactured similarly to Comparative Example B-O. An EL external quantum, yield calculated from the driving voltage and the front brightness of the EL device at 600cd/m² is sliown in Table 2. [Example B-2]

By using Compound (185) according to the present invention instead of NTD of 7nm as the hole transporting layer in the EL device according to Comparative Example B-O, an EL device was manufactured similarly to Comparative Example B-O. An EL external quantum yield calculated from the driving voltage and the front brightness of the EL device at 600cd/m² is sliown in Table 2. [Example B-3]

By using Compound (208) according to the present invention instead of NPD of 7nm as the hole transporting layer in the EL device according to Comparative Example B-O, an EL device was manufactured similarly to Comparative Example B-O. An EL external quantum yield calculated from the driving voltage and the front brightness of the EL device at 600cd/m² is shown in Table 2.

Table 2: Driving voltage and EL external quantum yield of the obtained devices at 600cd/m²

As can be seen apparently from Table 2, the EL devices using the compounds according to the present invention as the hole transporting layer exhibit relatively high light emission efficiency in comparison with the EL device according to the comparative example, and the voltage values with the same brightness are equal to or smaller than that of the EL device according to Comparative Example B-O from the view point of impπrvement in light emission efficiency. [Comparative Example C-O]

A cleaned ITO substrate was placed into a vapor deposition apparatus, 2-TNATA was deposited thereon as a hole injecting layer with a thickness of 140nm. NPD ((N,N'-di-α-naphthyl- N,N'-diphenyl)-benzidine) was deposited thereon as a hole transporting layer with a thickness of 7nm. Carbazole derivative (1) was deposited thereon as a hole injection promoting layer with a thickness of 3nm. Compound (P-2) as a light emitting material (P-2) and mCP as a host material were deposited on the resultant structure at a ratio (mass ratio) of 15:85 with a thickness of 30nm and BAIq was deposited thereon as an electron transporting layer with a thickness of 40nm. Thereafter, a patterned mask (of which the light emitting area is 4mmx5mm) was placed on the obtained organic thin film, lithium fluoride was deposited, thereon with a thickness of about lnm, and then aluminum was co-deposited thereon with a thickness of lOOnm, thereby manufacturing an EL device. As a result of applying a DC steady voltage to the EL device to emit light by the use of Source measure unit 2400 made by Toyo Corporation, blue light resulting from the light emitting material (P-2) could be obtained. An EL external quantum yield calculated from the driving voltage and the front brightness of the EL device at 400cd/m² is shown in Table 3.

Carbazole derivative (!)

2-TNATA

Light emitting material (P-2)

BAIq

[Example C-I]

By depositing Compound (5) according to the present invention with a thickness of IOnm instead of NPD of 7nm as the hole transporting layer and Car^"bazole derivative 1 of 3 nm as the hole injection promoting layer 1 in the EL device according to Comparative Example C-O, an EL device was manufactured similarly to Comparative Example C-O. An EL external quantum yield calculated from the driving voltage and the front brightness of the EL device at 400cd/m² is shown in Table 3. [Example C-2]

By depositing Compound (185) according to the present invention with a thickness of IOnm instead of NPD of 7nm as the hole transporting layer and Carbazole derivative 1 of 3 nm as the hole injection promoting layer 1 in the EL device accordήxg to Comparative Example C-O, an EL device was manufactured similarly to Comparative Example C-O. An EL external quantum yield calculated from the driving voltage and the front brightness of the EL device at 400cd/m² is shown in Table 3. [Example C-3]

By depositing Compound (208) according to the present invention with a thickness of IOnm instead of NPD of 7nm as the hole transporting layer and Carbazole derivative 1 of 3 nm as the hole injection promoting layer 1 in the EL device accordirtg to Comparative Example C-O, an EL device was manufactured similarly to Comparative Example C-O. An EL external quantum yield calculated from the driving voltage and the front brightness of the EL device at 400cd/m² is shown in Table 3. [Example C-4]

By depositing Compound (5) according to the present invention and Carbazole derivative 1 at a ratio (mass ratio) of 70:30 with a thickness of lOnm instead of NPD of 7nm as the hole transporting layer and Carbazole derivative 1 of 3 nm as the hole injection promoting layer 1 in the EL device according to Comparative Example C-O, an EL device was manufactured similarly to Comparative Example C-O. An EL external quantum yield calculated from the driving voltage and the front brightness of the EL device at 400cd/m² is shown in Table 3. [Example C-5]

By depositing Compound (185) according to the present invention and Carbazole derivative 1 at a ratio (mass ratio) of 70:30 with a thickness of lOnm instead of NPD of 7nm as the hole transporting layer and Carbazole derivative 1 of 3 nnα as the hole injection promoting layer 1 in the EL device according to Comparative Example C-O, an EL device was manufactured similarly to Comparative Example C-O. An EL external quantum yield calculated from the driving voltage and the front brightness of the EL device at 400cd/m² is sliown in Table 3. [Example C-6]

By depositing Compound (208) according to the present invention and Carbazole derivative 1 at a ratio (mass ratio) of 70:30 with a thickness of lOnm instead of NPD of 7nm as the hole transporting layer and Carbazole derivative 1 of 3 nm as the hole injection promoting layer 1 in the EL device according to Comparative Example C-O, an EL device was manufactured similarly to Comparative Example C-O. An EL external quantum yield calculated from the driving voltage and the front brightness of the EL device at 400cd/m² is slaown in Table 3.

Table 3: Driving voltage and EL external quantum yield of the obtained devices at 400cd/m²

As can be seen apparently from Table 3, the EL devices employing the hole injection promoting layer combined with the hole injecting layer containing the compounds according to the present invention exhibit relatively high light emission efficiency in comparison with the EL device according to the comparative example, and the voltage values with the same brightness are equal to or smaller than that of the EL device according to Comparative Example C-O from the view point of improvement in light emission efficiency.

As described above with reference to the comparative examples and the examples, the organic EL device using the compounds according to the present invention, as an adjacent layer can realize light emission with high efficiency and driving with a low voltage.

Industrial Applicability

The organic electroluminescent device having the compound according to the present invention has excellent durability. In addition, by using a compound having a specific structure in a specific layer of an organic layer, it is possible to emit light with high efficiency.

The entire disclosure of each and every foreign patent application from which the benefit of foreign priority has been claimed in the present application is incorporated herein by reference, as if fully set forth.

1. An organic electroluminescent device comprising: a pair of electrodes; and at least one organic layer between the pair of electrodes, wherein the at least one organic layer contains a compound represented by Formula (1):

wherein M represents a transition metal atom or a transition metal ion;

R¹¹ and R¹² each independently represents a hydrogen atom or a substituent group, and R¹¹ and R¹² may be independently bonded to M or R^π and R¹² may be bonded to each other to form a cyclic structure;

L¹¹ represents a ligand, and Lⁿ may be bonded to at least one of R¹¹ and R¹²;

2. The organic electroluminescent device according to claim 1, wherein the compound represented by Formula (1) is a compound represented by Formula

(2):

Formula ( 2)

wherein M represents a transition metal atom or a transition metal ion;

R²¹, R²², R²³ and R²⁴ each independently represents a hydrogen atom or a substituent group,

Claims

and R²¹, R²², R²³ and R²⁴ may be independently bonded to M or R²¹, R²², R²³ and R²⁴ may be bonded to each other to form a cyclic structure;

3. The organic electroluminescent device according to claim 2, wherein the compound represented by Formula

(2) is a compound represented by Formula

(3):

Formula ( 3 )

wherein M represents a transition metal atom or a transition metal ion;

L³¹ represents a ligand;

X³¹ represents a counter ion; n³¹ represents an integer of 0 to 4; n³² represents an integer of 1 to 3; n³³ represents an integer of 0 to 2; m³¹ represents an integer of 0 to 4; and C represents a carbene carbon, which is bonded to two nitrogen atoms to coordinate with M by means of two electrons of the carbene carbon.

4. The organic electroluminescent device according to claim 3, wherein the compound represented by Formula (3) is a compound represented by Formula

(4):

Formula ( 4 )

R⁴⁴, R⁴⁵ and R⁴⁶ each independently represents a substituent group, provided that when R⁴⁴, R⁴⁵ and R⁴⁶ are plural respectively, a plurality of R⁴⁴, a plurality of R⁴⁵ and a plurality of R⁴⁶ may be bonded to each other to form a cyclic structure respectively or R⁴⁴, R⁴⁵ and R⁴⁶ may coordinate with M through an atom of R⁴⁴, R⁴⁵ and R⁴⁶ respectively; n⁴¹ represents an integer of 0 to 2; n⁴² represents an integer of 1 to 3; and m⁴¹, m⁴² and m⁴³ each independently represents an integer of 0 to 4.

5. The organic electroluminescent device according to any of claims 1 to 4, wherein a ligand containing the carbene carbon is a tridentate to hexadentate ligand.

6. The organic electroluminescent device according to claim 1, wherein the compound represented by Formula (1) is a compound represented by Formula

(5):

Formula ( 5 )

R⁵⁴, R⁵⁵ and R⁵⁶ each independently represents a substituent group, provided that when R⁵⁴, R⁵⁵ and R⁵⁶ are plural respectively, a plurality of R⁵⁴, a plurality of R⁵⁵ and a plurality o>f R⁵⁶ may be bonded to each other to form a cyclic structure respectively;

7. The organic electroluminescent device according to any of claims 1 to 6, wherein the at least one organic layer includes a light emitting layer, and wherein the light emitting layer contains at least a light emitting material and a compound represented by any of Formulae (1) to (5).

8. The organic electroluminescent device according to any of claims 1 to 7, wherein the at least one organic layer includes a light emitting layer, and .. . wherein at least one layer between the light emitting layer and a positive electrode contains a compound represented by any of Formulae (1) to (5).

9. The organic electroluminescent device according to any of claims 1 to 7, wherein the at least one organic layer includes a light emitting layer, and wherein at least one layer between the light emitting layer and a negative electrode contains a compound represented by any of Formulae (1) to (5).