CN103524510A - Novel organic electroluminescent compounds and organic electroluminescent device using the same - Google Patents

Novel organic electroluminescent compounds and organic electroluminescent device using the same Download PDF

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CN103524510A
CN103524510A CN201310560064.2A CN201310560064A CN103524510A CN 103524510 A CN103524510 A CN 103524510A CN 201310560064 A CN201310560064 A CN 201310560064A CN 103524510 A CN103524510 A CN 103524510A
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alkyl
organic electroluminescent
aryl
compound
silyl
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CN103524510B (en
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金侈植
赵英俊
权赫柱
金奉玉
金圣珉
尹胜洙
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Rohm and Haas Electronic Materials Korea Ltd
Rohm and Haas Electronic Materials LLC
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Abstract

Disclosed are a novel organic electroluminescent compound and an organic electroluminescent device comprising the same. When used as host material of organic electroluminescent material of an OLED device, the disclosed organic electroluminescent compound exhibits high luminous efficiency and excellent life property of the material as compared to conventional host material. Therefore, it can be used to manufacture OLEDs having very good operation life.

Description

The organic electroluminescent device of new organic electroluminescent compounds and this compound of use
Patent application of the present invention is that international application no is PCT/KR2010/001647, international filing date is on March 17th, 2010, the application number that enters the China national stage is 201080022499.6, and name is called the dividing an application of application for a patent for invention of " new organic electroluminescent compounds and use the organic electroluminescent device of this compound ".
Technical field
The organic electroluminescent device that the present invention relates to novel organic electroluminescent compounds and comprise this compound.More particularly, the present invention relates to the novel organic electroluminescent compounds as electroluminescent material, and use them as the organic electroluminescent device of matrix (host).
Background technology
The greatest factor of luminous efficiency decision OLED(organic electroluminescent LED) is the type of electroluminescent material.Although up to the present fluorescent material has been widely used as electroluminescent material, from electroluminescent mechanism, exploitation phosphor material is in theory luminous efficiency to be improved and is up to one of best method of 4 times.
Up to the present, iridium (III) complex compound is well-known a kind of phosphor material, comprises (acac) Ir(btp) 2, Ir(ppy) 3and Firpic, respectively as redness, green and blue phosphorescent material.Specifically, many phosphor materials are studied in Japan, Europe and the U.S. at present.
As the substrate material of phosphorescent light-emitting materials, what be up to the present widely known by the people most is 4,4'-N, N'-bis-carbazoles-biphenyl (biphenyl) (CBP), and the known high efficiency OLED that has that has applied hole blocking layer (for example BCP and BAlq).Pioneer Electronic Corp. (Japan) reported use two (2-methyl-8-quinophenol (oxine) root (quinolinato)) (p-phenyl phenol root (phenolato)) aluminium (III) (BAlq) derivative as the high performance OLED of matrix.
Figure BDA0000412382150000021
Although material of the prior art has advantage from luminosity, they have the thermostability of low second-order transition temperature and non-constant, so these materials tend to change under high temperature and vacuum in gas-phase deposition process.In OLED, definition power efficiency=(π/voltage) * current efficiency.Therefore, power efficiency and voltage are inversely proportional to, and power efficiency should be higher to obtain lower OLED watt consumption.In practice, use the OLED of electrophosphorescence material to show that its current efficiency (cd/A) is obviously higher than the OLED of use fluorescence EL material.But, in the situation that use conventional material for example BAlq and CBP as the substrate material of phosphor material, aspect power efficiency (lm/w), there is no obvious advantage, this is to use the OLED of fluorescent material to have higher operating voltage because compare.And this OLED can not obtain satisfied equipment life.
Therefore, need to develop the further improved substrate material of stability and performance.
Summary of the invention
The description of invention technical problem
The present inventor has made great efforts to overcome the problem of routine techniques, thereby has invented the organic electroluminescent device that novel electroluminescent compounds is realized the equipment life that has excellent luminous efficiency and obviously extend.
Therefore, the object of the invention is to overcome the problems referred to above and the organic electroluminescent compounds that comprises skeleton is provided, to compare conventional substrate material, obtain the equipment life of higher luminous efficiency, raising and suitable chromaticity coordinates.
Another object of the present invention is to provide has high-level efficiency and long-life organic electroluminescent device, and it uses this organic electroluminescent compounds as electroluminescent material.
The method of dealing with problems
Specifically, the present invention relates to the organic electroluminescent compounds representing with one of chemical formula (1)-(5) and the organic electroluminescent device that comprises this compound.Because organic electroluminescent compounds of the present invention is compared conventional substrate material better luminous efficiency and excellent life performance are provided, therefore can obtain having the OLED of excellent working life.
[Chemical formula 1]
Figure BDA0000412382150000031
[Chemical formula 2]
Figure BDA0000412382150000032
[chemical formula 3]
Figure BDA0000412382150000041
[chemical formula 4]
Figure BDA0000412382150000042
[chemical formula 5]
Wherein,
X and Y are independently selected from N (Ar 1), O and S, wherein Ar 1can be mutually different, and when there being two or more Ar 1during group, Ar 1can be expressed as Ar 1or Ar 2;
Z 1to Z 8independently selected from C (Ar 3) and N, wherein Ar 3can be mutually different, and adjacent Ar 3group can be joined together to form ring;
Ar 1and Ar 2independently selected from (Cl-C60) alkyl, (C3-C60) cycloalkyl, the heteroatomic 5-that comprises one or more N of being selected from, O, S, Si and P or 6-unit Heterocyclylalkyl, (C7-C60) bicyclic alkyl, adamantyl, (C2-C60) thiazolinyl, (C2-C60) alkynyl, (C6-C60) aryl and (C3-C60) heteroaryl;
Ar 3independently selected from hydrogen, (Cl-C60) alkyl, halogen, cyano group, (C3-C60) cycloalkyl, comprise one or more N of being selected from, O, S, the heteroatomic 5-of Si and P or 6-unit Heterocyclylalkyl, (C7-C60) bicyclic alkyl, adamantyl, (C2-C60) thiazolinyl, (C2-C60) alkynyl, (C6-C60) aryl, (Cl-C60) alkoxyl group, (C6-C60) aryloxy, (C3-C60) heteroaryl, (C6-C60) arylthio, (Cl-C60) alkylthio, single-or two (Cl-C30) alkylamino, single-or two (C6-C30) virtue is amino, three (Cl-C30) alkyl silyl, two (Cl-C30) alkyl (C6-C30) aryl silyl, three (C6-C30) aryl silyl, single-or two (C6-C30) aryl boryl, single-or two (Cl-C60) boron alkyl alkyl, nitro and hydroxyl, and
Ar 1to Ar 3alkyl, cycloalkyl, Heterocyclylalkyl, bicyclic alkyl, adamantyl, thiazolinyl, alkynyl, aryl, alkoxyl group, aryloxy, heteroaryl, arylthio, alkylthio, alkylamino, virtue is amino, trialkylsilkl, di alkylaryl silyl, diarye silyl, aryl boryl or boron alkyl alkyl can further be replaced by the one or more substituting groups that are selected from lower group: (Cl-C60) alkyl, halogen, cyano group, (C3-C60) cycloalkyl, comprise one or more N of being selected from, O, S, the heteroatomic 5-of Si and P or 6-unit Heterocyclylalkyl, (C7-C60) bicyclic alkyl, adamantyl, (C2-C60) thiazolinyl, (C2-C60) alkynyl, (C6-C60) aryl, (Cl-C60) alkoxyl group, (C6-C60) aryloxy, P (=O) R ar b[R aand R brepresent independently (Cl-C60) alkyl or (C6-C60) aryl] (C6-C60) aryl of replacing, (C3-C60) heteroaryl, (C6-C60) (C3-C60) heteroaryl that aryl replaces, (Cl-C60) (C3-C60) heteroaryl that alkyl replaces, (C6-C60) aryl (Cl-C60) alkyl, (C6-C60) arylthio, (Cl-C60) alkylthio, single-or two (Cl-C30) alkylamino, single-or two (C6-C30) virtue is amino, three (Cl-C30) alkyl silyl, two (Cl-C30) alkyl (C6-C30) aryl silyl, three (C6-C30) aryl silyl, single-or two (C6-C30) aryl boryl, single-or two (Cl-C60) boron alkyl alkyl, nitro and hydroxyl, do not comprise that such situation: X and Y are N (Ar 1) and Z 1to Z 8all C (Ar 3).
As herein described comprising " (Cl-C60) alkyl ", the substituting group of part can comprise 1-60 carbon atom, 1-20 carbon atom or 1-10 carbon atom.The substituting group that comprises " (C6-C60) aryl " part can comprise 6-60 carbon atom, 6-20 carbon atom or 6-12 carbon atom.The substituting group that comprises " (C3-C60) heteroaryl " part can comprise 3-60 carbon atom, 4-20 carbon atom or 4-12 carbon atom.The substituting group that comprises " (C3-C60) cycloalkyl " part can comprise 3-60 carbon atom, 3-20 carbon atom or 3-7 carbon atom.The substituting group that comprises " (C2-C60) alkenyl or alkynyl " part can comprise 2-60 carbon atom, 2-20 carbon atom or 2-10 carbon atom.
Term of the present invention " alkyl " comprises the saturated univalence hydrocarbyl of straight or branched or its combination, and they can only be comprised of carbon atom and hydrogen atom.Term " alkoxyl group " expression-O-alkyl, wherein alkyl as above defines.
Term described herein " aryl " represents to remove by aromatic hydrocarbon the organic radical obtaining after a hydrogen atom.Aryl comprises monocycle or carbocyclic fused ring system, and each ring of aryl suitably comprises 4-7, preferred 5-6 annular atoms.Also can comprise that two or more aryl are by the structure of chemical bonds.Object lesson comprise phenyl, naphthyl, xenyl (biphenyl), anthryl, indenyl, fluorenyl, phenanthryl (phenanthryl), benzo [9,10] phenanthryl (triphenylenyl), pyrenyl, perylene base (perylenyl),
Figure BDA0000412382150000066
base (chrysenyl), naphthacenyl (naphthacenyl), fluoranthene base (fluoranthenyl) etc., but be not limited to this.
Term as herein described " heteroaryl " represents that in aromatic nucleus skeletal atom, comprising 1-4 is selected from the heteroatoms of N, O and S and the aryl that remaining aromatic nucleus skeletal atom is carbon atom.Described heteroaryl can be 5-or 6-unit's bicyclic heteroaryl or the polyheteroaromatic that condenses with one or more phenyl ring, and can be fractional saturation.Also can comprise the structure with one or more heteroaryls that connect by chemical bond.Described heteroaryl can comprise divalent aryl, its heteroatoms oxidation or quaternized formation N-oxide compound, quaternary ammonium salt etc.Concrete example comprises bicyclic heteroaryl for example furyl, thienyl, pyrryl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl group, isothiazolyl, different
Figure BDA0000412382150000061
azoles base,
Figure BDA0000412382150000062
azoles base, di azoly, triazinyl, tetrazine base, triazolyl, tetrazyl, furazan base (furazanyl), pyridyl, pyrazinyl, pyrimidyl, pyridazinyl; Polyheteroaromatic is benzofuryl, benzothienyl, isobenzofuran-base, benzimidazolyl-, benzothiazolyl, benzisothiazole base, benzisoxa for example
Figure BDA0000412382150000064
azoles base, benzo
Figure BDA0000412382150000065
azoles base, pseudoindoyl, indyl, indazolyl, diazosulfide base, quinolyl, isoquinolyl, cinnolines base (cinnolinyl), quinazolyl, quinolizinyl (quinolizinyl), quinoxalinyl (quinoxalinyl), carbazyl, phenanthridinyl (phenanthridinyl), benzo dioxolyl (benzodioxolyl); And corresponding N-oxide compound (for example pyridyl N-oxide compound, quinolyl N-oxide compound); And quaternary ammonium salt, but be not limited to this.
The example of organic electroluminescent compounds of the present invention can be the compound that one of following chemical formula represents:
Figure BDA0000412382150000071
Figure BDA0000412382150000081
Figure BDA0000412382150000091
Wherein: Ar 1and Ar 2as defined in chemical formula (1)-(5).
In addition, the example of organic electroluminescent compounds of the present invention can be the compound that one of following chemical formula represents:
Figure BDA0000412382150000101
Wherein: Ar 1and Ar 2as defined in chemical formula (1)-(5).
The object lesson of organic electroluminescent compounds of the present invention can be the compound that one of following chemical formula represents:
Figure BDA0000412382150000111
Wherein: Ar 1and Ar 2as defined in chemical formula (1)-(5).
More particularly, Ar 1and Ar 2represent independently the substituting group that phenyl, 1-naphthyl or one of 2-naphthyl or following chemical formula represent, but they are not limited to this.
Figure BDA0000412382150000112
Figure BDA0000412382150000121
The present invention also provides a kind of organic electroluminescent device, and it is by the first electrode, the second electrode and insert at least one deck organic layer between described the first electrode and the second electrode; Wherein said organic layer comprises the organic electroluminescent compounds that one of one or more chemical formulas (1)-(5) represent.
The feature of organic electroluminescent device of the present invention is that organic layer comprises electroluminescence layer, and this electroluminescence layer comprises that the compound of one of one or more chemical formulas (1)-(5) expression is as electroluminescent matrix and one or more phosphorescent dopants.The not concrete restriction of described doping agent.
Organic electroluminescent device of the present invention also can comprise that one or more are selected from the compound of aromatic amine compound and styryl aromatic amine compound, and the organic electroluminescent compounds that represents of one of one or more chemical formulas (1)-(5).
In organic electroluminescent device of the present invention, described organic layer also can comprise that one or more are selected from metal or its complex compound of the periodic table of elements the 1st, of family 2 families, period 4 and period 5 transition metal, lanthanide series metal and D-transition element, and the organic electroluminescent compounds that represents of one of one or more chemical formulas (1)-(5).Described organic layer can comprise electroluminescence layer and charge generation layer.
Except above-mentioned organic electroluminescent compounds, described organic electroluminescent device also can comprise the organic electro luminescent layer of one or more layers blue light-emitting, green glow or ruddiness, to form the organic electroluminescent device emitting white light.
The advantageous effects of invention
Organic electroluminescent compounds of the present invention demonstrates this material during as the substrate material of the electroluminescent organic material of OLED and has good luminous efficiency and good life performance, so can be manufactured and be had the very OLED in good berth life-span by this compound.
Embodiments of the present invention
Also by further describing the present invention with reference to preparation example and embodiment, so that the luminescent properties of representational organic electroluminescent compounds of the present invention, its preparation method and electroluminescence device to be described, but be to provide these embodiment only for understanding better embodiments of the present invention, rather than be used for limiting the scope of the invention by any way.
Preparation example
Preparation example 1: prepare compound (A)
prepare compound (A-1)
Bromo-2-oil of mirbane (30g, 148.5mmol), 1-naphthalene boronic acids (1-naphtaleneboronic acid) (30.6g, 178.2mmol), Pd (PPh 3) 4(5.14g, 4.45mmol), 2M K 2cO 3the aqueous solution (297.01mmol), the mixture of toluene (500mL) and ethanol (200mL) stirs 4 hours at reflux conditions.By after mixture cool to room temperature, add wherein distilled water.Gained mixture is extracted with ethyl acetate, extract dried over mgso, and underpressure distillation.By column purification, obtain compound (A-1) (31g, 124.3mmol, 84.03%).
Prepare compound (A-2)
The mixture return stirring of compound (A-1) (31g, 124.3mmol) and triethyl-phosphite (300mL) 10 hours.By after mixture cool to room temperature, organic solvent is fallen in underpressure distillation.Add wherein distilled water, and described mixture is extracted with ethyl acetate.Extract dried over mgso, and underpressure distillation.By column purification, obtain compound (A-2) (18g, 82.84mmol, 66.81%).
Prepare compound (A-3)
Compound (A-2) (18g, 82.84mmol), l, 5-phenylbenzene-3-chloropyridine (26.4g, 99.41mmol), Pd (OAc) 2(1.85g, 8.28mmol), P (t-bu) 3(8.17ml, 16.5mmol, in dimethylbenzene 50%), the mixture return stirring of NaOt-bu (23.8g, 248.5mmol) and toluene (500mL) 12 hours.By after described mixture cool to room temperature, add wherein distilled water, and described mixture is extracted with ethyl acetate.Extract dried over mgso, and underpressure distillation.By column purification, obtain compound (A-3) (19g, 42.54mmol, 51.36%).
Prepare compound (A-4)
To compound (A-3) (19g, 42.54mmol), be dissolved in DMF(200mL) solution in add NBS (8.33g, 46.80mmol).In room temperature, place after 10 hours, organic solvent is fallen in underpressure distillation.Add wherein distilled water, and described mixture is extracted with ethyl acetate.Extract dried over mgso, and underpressure distillation.By column purification, obtain compound (A-4) (20g, 38.06mmol, 89.47%).
Prepare compound (A-5)
In-78 ℃ to being dissolved in THF(200mL) compound (A-4) solution in slowly add n-buLi (15.22mL, 38.06mmol, 2.5M in hexane).Stir after 1 hour, add wherein trimethyl borate.Described mixture is slowly warmed up to room temperature, and stirs 12 hours.Add wherein distilled water, and described mixture is extracted with ethyl acetate.Extract dried over mgso, and underpressure distillation.By column purification, obtain compound (A-5) (8g, 16.31mmol, 42.86%).
Prepare compound (A-6)
Compound (A-5) (8g, 16.31mmol), bromo-2-oil of mirbane (3.95g, 19.57mmol), Pd (PPh 3) 4(0.56g, 0.48mmol), 2M K 2cO 3the aqueous solution (16mL, 32.62mmol), the mixture return stirring of toluene (70mL) and ethanol (20mL).According to the step identical with synthetic compound (A-1), obtain compound (A-6) (7g, 12.33mmol, 75.62%).
Prepare compound (A-7)
Compound (A-6) (7g, 12.33mmol) mixes with triethyl-phosphite (100mL), and obtains compound (A-7) (4g, 7.46mmol, 58.33%) according to the step identical with synthetic compound (A-2).
Prepare compound (A)
Compound (A-7) (4g, 7.46mmol), iodobenzene (1.25mL, 11.20mmol), copper powder (0.71g, 11.20mmol), K 2cO 3(3.09g), the mixture return stirring 15 hours of 18-hat-6 (0.15g, 0.59mmol) and 1,2-dichlorobenzene (100mL).By after reaction mixture cool to room temperature, organic solvent is fallen in underpressure distillation.Add wherein distilled water, and described mixture is extracted with ethyl acetate.Extract obtains compound (A) (3.6g, 5.88mmol, 78.88%) by column purification.
Preparation example 2: prepare compound (B)
Figure BDA0000412382150000171
Prepare compound (B-1)
L, 4-bis-is bromo-2,3-dinitrobenzene (20g, 61.36mmol), 1-naphthalene boronic acids (26g, 153.42mmol), Pd (PPh 3) 4(3.54g, 3.06mmol), 2M K 2cO 3the aqueous solution (90mmol), the mixture of toluene (200mL) and ethanol (100mL) stirs 10 hours at reflux conditions.By after described reaction mixture cool to room temperature, add wherein distilled water, and described mixture is extracted with ethyl acetate.Extract dried over mgso, and underpressure distillation.By column purification, obtain compound (B-1) (22g, 52.32mmol, 85.28%).
Prepare compound (B-2)
Compound (B-1) (22g, 52.32mmol) and triethyl-phosphite (200mL) mix, and 180 ℃ of stirrings.According to the step identical with synthetic compound (A-2), obtain compound (B-2) (10g, 28.05mmol, 53.95%).
Prepare compound (B-3)
Compound (B-2) (10g, 28.05mmol), 2-iodine naphthalene (7.1g, 28.05mmol), copper powder (2.67g, 42.08mmol), K 2cO 3(11.63g, 84.17mmol), the mixture of 18-hat-6 (0.59g, 2.24mmol) and 1,2-dichlorobenzene (100mL) was in 190 ℃ of return stirrings 20 hours.After cool to room temperature, organic solvent is fallen in underpressure distillation.Add wherein distilled water, and described mixture is extracted with ethyl acetate.Extract dried over mgso, and underpressure distillation.By column purification, obtain compound (B-3) (4g, 8.28mmol, 29.60%).
Prepare compound (B)
To comprising, be dissolved in DMF(20mL) the reaction vessel of NaH (0.49g, 12.43mmol, 60% dispersion liquid in mineral oil) solution in add be dissolved in DMF(20mL) the solution of compound (B-3) (4g, 8.28mmol).After 1 hour, 2-is chloro-4, and 6-phenylbenzene triazine (2.66g, 9.94mmol) is dissolved in DMF(20mL) solution add wherein.Stir after 12 hours, add distilled water, and the solid filtration under diminished pressure making.From ethyl acetate and DMF recrystallization, obtain compound (B) (3.5g, 4.90mmol, 59.21%).
Preparation example 3: prepare compound (C)
Figure BDA0000412382150000181
Prepare compound (C-1)
To 1,2-cyclohexyl diketone (42.52g, 379.26mmol), be dissolved in the solution of ethanol (1000mL) and slowly add 2-naphthyl hydrazine (20g, 126.42mmol).Add wherein acetic acid (0.28mL, 5.05mmol), and mixture is heated to 40 ℃.After 2 hours, cooling described mixture, and add wherein distilled water.Prepared solid filtration under diminished pressure obtains compound (C-1) (17g, 67.37mmol, 53.47%).
Prepare compound (C-2)
To compound (C-1) (17g, 67.37mmol), be dissolved in the solution of acetic acid (100mL) and add trifluoroacetic acid (10mL).In stirring at room, after 2 hours, add wherein distilled water.NaOH aqueous solution neutralization for mixture, and be extracted with ethyl acetate.Extract dried over mgso, and underpressure distillation.By column purification, obtain compound (C-2) (11g, 46.75mmol, 69.39%).
Prepare compound (C-3)
According to the step identical with synthetic compound (B-3), obtain compound (C-3) (10g, 32.11mmol, 68.69%).
Prepare compound (C-4)
According to the step identical with synthetic compound (C-1), obtain compound (C-4) (12g, 29.88mmol, 93.07%).
Prepare compound (C-5)
According to the step identical with synthetic compound (C-2), obtain compound (C-5) (6g, 15.68mmol, 52.50%).
Prepare compound (C)
According to the step identical with synthetic compound (B), obtain compound (C) (5g, 8.14mmol, 51.95%).
Preparation example 4: prepare compound (D)
Prepare compound (D-2)
According to the step identical with synthetic example (A-1), but use compound (D-1) to obtain compound (D-2) (11g, 38.02mmol, 89.22%).
Prepare compound (D-3)
According to the step identical with synthetic compound (A-2), obtain compound (D-3) (8g, 31.09mmol, 81.78%).
Prepare compound (D)
According to the step identical with synthetic compound (B), obtain compound (D) (6g, 12.30mmol, 38.70%).
Preparation example 5: prepare compd E and F
Figure BDA0000412382150000201
Prepare compound (E-2)
According to the step identical with synthetic compound (A-1), but use compound (E-1) to obtain compound (E-2) (15g, 51.85mmol, 86.51%).
Prepare compound (E-3)
According to the step identical with synthetic compound (A-2), obtain compound (E-3) (6g, 23.31mmol, 44.97%).
Prepare compound (E)
According to the step identical with synthetic compound (B), obtain compound (E) (5g, 10.25mmol, 43.99%).
Prepare compound (F-1)
According to the step identical with synthetic compound (A-2), obtain compound (F-1) (3g, 11.65mmol, 22.48%).
Prepare compound (F)
According to the identical step of synthetic compound (B), obtain compound (F) (3g, 6.15mmol, 52.81%).
Preparation example 6: prepare compound (G) and (H)
Figure BDA0000412382150000211
Prepare compound (G-1)
Carbazole (20g, 119.6mmol), iodobenzene (20mL, 179.41mmol), copper (11.4g, 179.41mmol), K 2cO 3(49g, 358.8mmol), the mixture of 18-hat-6 (2.5g, 9.56mmol) and 1,2-dichlorobenzene (100mL) stirs 12 hours in 190 ℃.After cool to room temperature, reaction mixture underpressure distillation.Add wherein distilled water, and gained mixture is extracted with ethyl acetate.Extract dried over mgso, and underpressure distillation.By column purification, obtain compound (G-1) (22g, 90.42mmol, 75.60%).
Prepare compound (G-2)
According to the step identical with synthetic compound (A-4), obtain compound (G-2) (25g, 77.59mmol, 85.81%).
Prepare compound (G-3)
According to the step identical with synthetic compound (A-5), obtain compound (G-3) (11g, 38.31mmol, 49.37%).
Prepare compound (G-4)
According to the step identical with synthetic compound (A-1), obtain compound (G-4) (12g, 32.84mmol, 85.72%).
Prepare compound (G-5)
According to the step identical with synthetic compound (A-2), react and within 4 hours, obtain compound (G-5) (6g, 17.99mmol, 54.80%).
Prepare compound (G)
According to the step identical with synthetic compound (B), obtain compound (G) (7g, 12.39mmol, 68.91%).
Prepare compound (H-1)
According to the step identical with synthetic compound (A-2), react and within 4 hours, obtain compound (H-1) (2g, 5.99mmol, 18.26%).
Prepare compound (H)
According to the step identical with synthetic compound (B), obtain compound (H) (1.7g, 3.01mmol, 50.26%).
According to the step of preparation example (1)-(6), be prepared with organic electro luminescent compounds (TA, TB and TC).Substituting group (the Ar of the organic electroluminescent compounds that these make 1and Ar 2) and these compounds 1h NMR and MS/FAB data rows are in following table 1 and 2.
Table 1
Figure BDA0000412382150000231
Figure BDA0000412382150000241
Figure BDA0000412382150000261
Figure BDA0000412382150000271
Figure BDA0000412382150000281
Figure BDA0000412382150000291
Figure BDA0000412382150000321
Figure BDA0000412382150000331
Table 2
Figure BDA0000412382150000341
Figure BDA0000412382150000351
Figure BDA0000412382150000361
[embodiment 1-10] used organic electroluminescent compounds of the present invention to manufacture OLED
Use electroluminescent compounds of the present invention to manufacture OLED equipment.
First, the transparency electrode ito thin film (15 Ω/) (purchased from SCP company) for OLED of being made by glass is carried out to ultrasonic cleaning with trieline, acetone, ethanol and distilled water successively, and be stored in Virahol before using.
Then, ITO substrate is contained in the substrate folder (folder) of vacuum phase deposition equipment, by by following chemical structural formula, represented 4,4', 4 " tri-(N; N-(2-naphthyl)-phenyl amino) triphenylamine (2-TNATA) is placed in the cell (cell) of vacuum phase deposition equipment, is then vented to indoor vacuum tightness and is up to 10 -6holder.Cell is applied to electric current, makes 2-TNATA evaporation, thus on ITO substrate the hole injection layer of vapour deposition 60 nano thickness.
Then, in another cell of this vacuum phase deposition equipment, add N, N'-bis-(Alpha-Naphthyl)-N, N'-phenylbenzene-4,4'-diamines (NPB), to cell apply electric current with evaporation NPB, thereby on hole injection layer the hole transport layer of vapour deposition 20 nano thickness.
To adding compound of the present invention in a cell of vapor deposition apparatus, (it is 10 -6holder is lower to vacuum-sublimation purifying) (for example, compound TA8-H4-H2), and for example, by electroluminescent doping agent (, compound (piq) 2ir(acac)) add in another cell.Bi-material adulterates with the concentration of 4-10 % by mole with the evaporation of different speed, thus on hole transport layer the electroluminescence layer of vapour deposition 30 nano thickness.
Figure BDA0000412382150000372
Then, three (oxine) aluminium (III) that following structural formula is represented (Alq) vapour deposition is the electron transport layer of 20 nano thickness, by oxine lithium (lithium quinolate) (Liq) vapour deposition be the electron injecting layer of 1-2 nanometer thickness.Then, adopt another vacuum phase deposition equipment, the Al negative electrode of vapour deposition 150 nanometer thickness, manufactures OLED.
Figure BDA0000412382150000381
[embodiment 11-20] used electroluminescent compounds of the present invention to manufacture OLED
According to the step that the OLED with embodiment 1-10 is identical, manufacture OLED, but use compound of the present invention (for example compound TA4-H4-H4) as organic iridium complex (Ir (ppy) of substrate material and following chemical formulation 3) as electroluminescent doping agent.
Figure BDA0000412382150000382
[comparative example 1 and 2] used conventional electroluminescent material to manufacture OLED
According to the step identical with the embodiment of the present invention 1 and 11, manufacture OLED, but (p-phenyl phenol root) aluminium (III) (BAlq) in another cell of vacuum phase deposition equipment, to add two (2-methyl 8-quinophenol (oxine) roots), rather than electroluminescent compounds of the present invention, as substrate material.
Figure BDA0000412382150000391
At 1000cd/cm 2they comprise organic electroluminescent compounds of the present invention to measure embodiment 1-10 and embodiment 11-20() and comparative example 1 and 2(they comprise conventional electroluminescent compounds) operating voltage and the power efficiency of the OLED that manufactures, the results are shown in table 3 and 4.
From table 3 and 4, the organic electroluminescent compounds of the present invention's exploitation is compared conventional material and is had excellent performance aspect equipment performance.
Table 3
Figure BDA0000412382150000392
Table 4
Figure BDA0000412382150000401
As shown in Table 3, compare with conventional material, the compound of the present invention's exploitation shows excellent performance aspect luminosity.Compare with the equipment of comparative example 1 with conventional material manufacture, the equipment of manufacture of the present invention shows excellent current capability, thereby operating voltage is reduced to 1V or more.Compare with the equipment of comparative example 1, they also show that current efficiency performance is at least the former 1.4 times, and this is because luminescent properties is improved significantly.
As shown in Table 4, when the compound of the present invention's exploitation is used as the matrix of green electroluminescent, compare with the equipment of comparative example 2, described equipment shows because they have excellent luminescent properties the much higher power efficiency of 1.6 times that is at least the former.Compare with conventional material, excellent luminescent properties is confirmed.Particularly, compare with the equipment of comparative example 1, the equipment of embodiment 14 can be worked under the voltage that reduces 2.7V, and the equipment of embodiment 17 shows that operating voltage is 5.5V, at 1000cd/m 2power efficiency be 15.9lm/.
Therefore, the equipment that uses electroluminescent compounds of the present invention to send ruddiness or green glow as substrate material shows excellent luminescent properties, reduce operating voltage simultaneously, cause so the particularly power efficiency of the equipment of green light to increase 5.1-7.7lm/W, result is to improve watt consumption.

Claims (9)

1. the organic electroluminescent compounds being represented by one of following Chemical formula 1-5:
Chemical formula 5
Wherein:
X and Y are independently selected from N (Ar 1), O and S, wherein Ar 1can be mutually different, and when there being two or more Ar 1during group, Ar 1can be expressed as Ar 1or Ar 2;
Z 1to Z 8independently selected from C (Ar 3) and N, wherein Ar 3can be mutually different, and adjacent Ar 3group can be joined together to form ring;
Ar 1and Ar 2independently selected from (Cl-C60) alkyl, (C3-C60) cycloalkyl, the heteroatomic 5-that comprises one or more N of being selected from, O, S, Si and P or 6-unit Heterocyclylalkyl, (C7-C60) bicyclic alkyl, adamantyl, (C2-C60) thiazolinyl, (C2-C60) alkynyl, (C6-C60) aryl and (C3-C60) heteroaryl;
Ar 3independently selected from hydrogen, (Cl-C60) alkyl, halogen, cyano group, (C3-C60) cycloalkyl, comprise one or more N of being selected from, O, S, the heteroatomic 5-of Si and P or 6-unit Heterocyclylalkyl, (C7-C60) bicyclic alkyl, adamantyl, (C2-C60) thiazolinyl, (C2-C60) alkynyl, (C6-C60) aryl, (Cl-C60) alkoxyl group, (C6-C60) aryloxy, (C3-C60) heteroaryl, (C6-C60) arylthio, (Cl-C60) alkylthio, single-or two (Cl-C30) alkylamino, single-or two (C6-C30) virtue is amino, three (Cl-C30) alkyl silyl, two (Cl-C30) alkyl (C6-C30) aryl silyl, three (C6-C30) aryl silyl, single-or two (C6-C30) aryl boryl, single-or two (Cl-C60) boron alkyl alkyl, nitro and hydroxyl, and
Ar 1to Ar 3alkyl, cycloalkyl, Heterocyclylalkyl, bicyclic alkyl, adamantyl, thiazolinyl, alkynyl, aryl, alkoxyl group, aryloxy, heteroaryl, arylthio, alkylthio, alkylamino, virtue is amino, trialkylsilkl, di alkylaryl silyl, diarye silyl, aryl boryl or boron alkyl alkyl can further be replaced by the one or more substituting groups that are selected from lower group: (Cl-C60) alkyl, halogen, cyano group, (C3-C60) cycloalkyl, comprise one or more N of being selected from, O, S, the heteroatomic 5-of Si and P or 6-unit Heterocyclylalkyl, (C7-C60) bicyclic alkyl, adamantyl, (C2-C60) thiazolinyl, (C2-C60) alkynyl, (C6-C60) aryl, (Cl-C60) alkoxyl group, (C6-C60) aryloxy, P (=O) R ar b[R aand R brepresent independently (Cl-C60) alkyl or (C6-C60) aryl] (C6-C60) aryl of replacing, (C3-C60) heteroaryl, (C6-C60) (C3-C60) heteroaryl that aryl replaces, (Cl-C60) (C3-C60) heteroaryl that alkyl replaces, (C6-C60) aryl (Cl-C60) alkyl, (C6-C60) arylthio, (Cl-C60) alkylthio, single-or two (Cl-C30) alkylamino, single-or two (C6-C30) virtue is amino, three (Cl-C30) alkyl silyl, two (Cl-C30) alkyl (C6-C30) aryl silyl, three (C6-C30) aryl silyl, single-or two (C6-C30) aryl boryl, single-or two (Cl-C60) boron alkyl alkyl, nitro and hydroxyl,
Do not comprise that such situation: X and Y are N (Ar 1) and Z 1to Z 8all C (Ar 3).
2. organic electroluminescent compounds as claimed in claim 1, is characterized in that, described compound is selected from following compound:
Wherein: Ar 1and Ar 2as claim 1 defines.
3. organic electroluminescent compounds as claimed in claim 1, is characterized in that, described compound is selected from following compound:
Figure FDA0000412382140000051
Wherein: Ar 1and Ar 2as claim 1 defines.
4. an organic electroluminescent device, described equipment comprises the organic electroluminescent compounds described in any one in claim 1-3.
5. organic electroluminescent device as claimed in claim 4, is characterized in that, described equipment comprises the first electrode; The second electrode; And inserting one or more layers organic layer between described the first electrode and the second electrode, described organic layer comprises the organic electroluminescent compounds described in any one and one or more phosphorescent dopants in one or more claims 1-4.
6. organic electroluminescent device as claimed in claim 5, is characterized in that, described organic layer also comprises that one or more are selected from the amine compound of aromatic amine compound and styryl aromatic amine compound.
7. organic electroluminescent device as claimed in claim 5, it is characterized in that, described organic layer also comprises that one or more are selected from the periodic table of elements the 1st, of family 2 families, period 4 and the metal of period 5 transition metal, lanthanide series metal and d-transition element or the complex compound being formed by them.
8. organic electroluminescent device as claimed in claim 5, is characterized in that, described organic layer comprises electroluminescence layer and charge generation layer.
9. organic electroluminescent device as claimed in claim 5, is characterized in that, described equipment is the organic electroluminescence equipment emitting white light, and described organic layer comprises the organic electro luminescent layer of one or more layers blue light-emitting, ruddiness or green glow simultaneously.
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