CN1666577A - 带电子迁移和/或抗淬灭层的电子器件 - Google Patents
带电子迁移和/或抗淬灭层的电子器件 Download PDFInfo
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- CN1666577A CN1666577A CN038161885A CN03816188A CN1666577A CN 1666577 A CN1666577 A CN 1666577A CN 038161885 A CN038161885 A CN 038161885A CN 03816188 A CN03816188 A CN 03816188A CN 1666577 A CN1666577 A CN 1666577A
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- integer
- heteroaryl
- alkylidene
- layer
- aryl
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- 238000010791 quenching Methods 0.000 title 1
- 230000027756 respiratory electron transport chain Effects 0.000 claims description 48
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 125000001118 alkylidene group Chemical group 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 125000001072 heteroaryl group Chemical group 0.000 claims description 18
- 238000004770 highest occupied molecular orbital Methods 0.000 claims description 13
- 241001597008 Nomeidae Species 0.000 claims description 11
- 125000000304 alkynyl group Chemical group 0.000 claims description 11
- 125000002769 thiazolinyl group Chemical group 0.000 claims description 11
- -1 alkylidene aryl Chemical group 0.000 claims description 9
- NSMJMUQZRGZMQC-UHFFFAOYSA-N 2-naphthalen-1-yl-1H-imidazo[4,5-f][1,10]phenanthroline Chemical compound C12=CC=CN=C2C2=NC=CC=C2C2=C1NC(C=1C3=CC=CC=C3C=CC=1)=N2 NSMJMUQZRGZMQC-UHFFFAOYSA-N 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 230000000694 effects Effects 0.000 claims description 6
- 125000005024 alkenyl aryl group Chemical group 0.000 claims description 4
- 125000005025 alkynylaryl group Chemical group 0.000 claims description 4
- 229910052723 transition metal Inorganic materials 0.000 claims description 3
- 150000003624 transition metals Chemical class 0.000 claims description 3
- 239000000203 mixture Substances 0.000 abstract description 40
- 239000010410 layer Substances 0.000 description 135
- 150000001875 compounds Chemical class 0.000 description 44
- 239000000463 material Substances 0.000 description 44
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- 230000000052 comparative effect Effects 0.000 description 28
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 21
- 238000005481 NMR spectroscopy Methods 0.000 description 20
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 20
- 239000000047 product Substances 0.000 description 20
- 238000000034 method Methods 0.000 description 19
- 238000002360 preparation method Methods 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 229910052757 nitrogen Inorganic materials 0.000 description 18
- 229910052741 iridium Inorganic materials 0.000 description 17
- 239000007787 solid Substances 0.000 description 17
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 11
- 229910052751 metal Inorganic materials 0.000 description 11
- 239000002184 metal Substances 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 238000013508 migration Methods 0.000 description 10
- 230000005012 migration Effects 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- ROJZKPKOWHXGLB-UHFFFAOYSA-N 2-thiophen-2-yl-5-(trifluoromethyl)pyridine Chemical compound N1=CC(C(F)(F)F)=CC=C1C1=CC=CS1 ROJZKPKOWHXGLB-UHFFFAOYSA-N 0.000 description 7
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- 125000004429 atom Chemical group 0.000 description 7
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
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- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
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- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 4
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- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
- 239000012965 benzophenone Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 3
- QKLWAMMQKBOTCD-UHFFFAOYSA-N butane;diphenylphosphane Chemical compound CCCC.C=1C=CC=CC=1PC1=CC=CC=C1 QKLWAMMQKBOTCD-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 3
- 150000004880 oxines Chemical class 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- CBHCDHNUZWWAPP-UHFFFAOYSA-N pecazine Chemical compound C1N(C)CCCC1CN1C2=CC=CC=C2SC2=CC=CC=C21 CBHCDHNUZWWAPP-UHFFFAOYSA-N 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 3
- 238000006276 transfer reaction Methods 0.000 description 3
- 238000001291 vacuum drying Methods 0.000 description 3
- VEUMBMHMMCOFAG-UHFFFAOYSA-N 2,3-dihydrooxadiazole Chemical compound N1NC=CO1 VEUMBMHMMCOFAG-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UVSSPWOKVSKHCU-UHFFFAOYSA-N [2-(trifluoromethyl)phenoxy]boronic acid Chemical compound OB(O)OC1=CC=CC=C1C(F)(F)F UVSSPWOKVSKHCU-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 239000004411 aluminium Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
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- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
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- JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
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- 230000003287 optical effect Effects 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000005424 photoluminescence Methods 0.000 description 2
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
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- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
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- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
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- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 2
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- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 2
- FMCAFXHLMUOIGG-IWFBPKFRSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2r)-2-formamido-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,5-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoic acid Chemical compound O=CN[C@@H](CS)C(=O)N[C@@H](C(C)C)C(=O)N[C@H](C(=O)N[C@@H](CCSC)C(O)=O)CC1=CC(C)=C(O)C=C1C FMCAFXHLMUOIGG-IWFBPKFRSA-N 0.000 description 1
- PHBVXHIVWULVNF-UHFFFAOYSA-N (4-fluorophenoxy)boronic acid Chemical compound OB(O)OC1=CC=C(F)C=C1 PHBVXHIVWULVNF-UHFFFAOYSA-N 0.000 description 1
- HMTSWYPNXFHGEP-UHFFFAOYSA-N (4-methylphenyl)methanamine Chemical compound CC1=CC=C(CN)C=C1 HMTSWYPNXFHGEP-UHFFFAOYSA-N 0.000 description 1
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 1
- PIINXYKJQGMIOZ-UHFFFAOYSA-N 1,2-dipyridin-2-ylethane-1,2-dione Chemical compound C=1C=CC=NC=1C(=O)C(=O)C1=CC=CC=N1 PIINXYKJQGMIOZ-UHFFFAOYSA-N 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- NBYLBWHHTUWMER-UHFFFAOYSA-N 2-Methylquinolin-8-ol Chemical compound C1=CC=C(O)C2=NC(C)=CC=C21 NBYLBWHHTUWMER-UHFFFAOYSA-N 0.000 description 1
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- KJXASRYNEVZVOM-UHFFFAOYSA-N 2-iodo-1,10-phenanthroline Chemical compound C1=CN=C2C3=NC(I)=CC=C3C=CC2=C1 KJXASRYNEVZVOM-UHFFFAOYSA-N 0.000 description 1
- OXPDQFOKSZYEMJ-UHFFFAOYSA-N 2-phenylpyrimidine Chemical group C1=CC=CC=C1C1=NC=CC=N1 OXPDQFOKSZYEMJ-UHFFFAOYSA-N 0.000 description 1
- FSEXLNMNADBYJU-UHFFFAOYSA-N 2-phenylquinoline Chemical compound C1=CC=CC=C1C1=CC=C(C=CC=C2)C2=N1 FSEXLNMNADBYJU-UHFFFAOYSA-N 0.000 description 1
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 1
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- SFBHJDZYFDQEEY-UHFFFAOYSA-N 9-cyclobutylcarbazole Chemical compound C1CCC1N1C2=CC=CC=C2C2=CC=CC=C21 SFBHJDZYFDQEEY-UHFFFAOYSA-N 0.000 description 1
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- CPPSKBIDQKJJKE-UHFFFAOYSA-N [3-(trifluoromethyl)phenoxy]boronic acid Chemical compound OB(O)OC1=CC=CC(C(F)(F)F)=C1 CPPSKBIDQKJJKE-UHFFFAOYSA-N 0.000 description 1
- HCIMXTXCDVBLOA-UHFFFAOYSA-N [4-(trifluoromethyl)phenoxy]boronic acid Chemical compound OB(O)OC1=CC=C(C(F)(F)F)C=C1 HCIMXTXCDVBLOA-UHFFFAOYSA-N 0.000 description 1
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Abstract
本发明涉及一种光活性电子器件,它包括阳极、阴极和光活性层。所述器件还包括电子迁移和/或抗淬灭层,它能将光活性层的电子转移淬灭和能量转移淬灭降至最小。
Description
发明的背景
相关申请
本申请要求2002年7月10日提交的美国临时申请60/394767和2003年3月28日提交的美国临时申请60/458277的优先权。
技术领域
本发明涉及一种光活性电子器件,其中至少有一层活性层包括一种电子迁移和/或抗淬灭组合物。
相关技术的描述
在有机光活性电子器件(例如制造有机发光二极管显示器的发光二极管(OLED))中,有机活性层夹在有机发光二极管显示器的两层电气接触层之间。在有机发光二极管中,通过向两层透光电接触层施加电压,所述有机光活性层透过所述电气接触层发射光线。
已知在发光二极管中使用有机场致发光化合物作为活性组分。业已使用简单的有机分子、共轭聚合物和有机金属配合物。
使用光活性物质的器件通常包括一层或多层电荷迁移层,该电荷迁移层位于光活性(例如发光)层和一层所述电气接触层之间。一层空穴迁移层可置于所述光活性层和空穴注入接触层(也称为阳极(anode))之间。一层电子迁移层可置于所述光活性层和电子注入接触层(也称为阴极(cathode))之间。
当有机金属化合物(例如铱和铂配合物)用作场致发光层时,在阴极一侧靠近发光层插入的阻挡层可增强器件的效率。Baldo等使用2,9-二甲基-4,7-二苯基-1,10-菲咯啉(称为BCP或DDPA)用于该目的。业已提出,BCP层起“激发子阻断器”的作用,防止发光激发子的能量转移至相邻层。所述阻断层的特征在于其带隙超过形成在发光层中的激发子的能级。
美国专利6,097.147公开了一种发光器件,它包括基本透明的阳极、在所述阳极上方的空穴迁移层、在所述空穴迁移层上方的发射层、在所述发射层上方的阻断层、在所述阻断层上方的电子迁移层和与所述电子迁移层电气接触的阴极。它还公开了一种器件,其中所述阻断层的特征在于其带隙大于形成在所述发射层中的激发子的能级。
但是,由光活性材料至相邻层的能量转移不仅会被能量转移所淬灭,而且还会被电子转移至相邻层所淬灭,因此光使用更大的带隙激发子阻断层是不够的。需要能防止能量转移淬灭和电子转移淬灭的材料。
发明的概述
本发明涉及一种光活性器件,它包括阳极、阴极和光活性层,它还包括使所述光活性层的电子转移淬灭和能量转移淬灭最小化的电子迁移和/或抗淬灭层。
在一个实例中,提供一种光活性电子器件,它包括:
(a)一个阳极;
(b)一个阴极,所述阴极的功函能级为E3;
(c)在所述阳极和所述阴极之间的光活性层,所述光活性层包括过渡金属的环金属化的配合物,所述环金属化的配合物具有LUMO能级E2和HOMO能级E4;
(d)置于所述阴极和所述光活性层之间的电子迁移和/或抗淬灭层,所述电子迁移和/或抗淬灭层的LUMO能级为E1和HOMO能级为E5;
条件是:
(1)E1-E3<1V;
(2)E1-E2>-1V;
(3)E4-E5>-1V。
在本文中,术语“电荷迁移组分(composition)”是指一种材料,它能从电极接受电荷,有助于沿该材料的厚度以相对高的效率迁移,并且电荷的损耗小。空穴迁移组分能够接受来自阳极的正电荷并迁移之。电子迁移组分能够接受来自阴极的负电荷并迁移之。
术语“抗淬灭组分”是指一种材料,它能够防止、阻滞或者减少向光活性层激发态的能量迁移和电子迁移和/或由光活性层激发态向相邻层的能量迁移和电子迁移。
术语“光活性”是指显示场致发光、光致发光和/或光敏性的任何材料。
术语“HOMO”是指化合物的最高占据分子轨道。
术语“LUMO”是指化合物的最低未占据分子轨道。
术语“基团”是指化合物的一部分,例如有机化合物中的取代基。
前缀“杂”是指一个或多个碳原子被不同的原子所取代。
术语“烷基”是指具有一个连接点位的由脂肪烃形成的基团,该基团可以是未取代的或者是取代的。
术语“杂烷基”是指至少具有一个杂原子并具有一个连接点位的由脂肪烃形成的基团,该基团可以是取代的或者是未取代的。
术语“亚烷基”是指具有两个或多个连接点位的由脂肪烃形成的基团。
术语“亚杂烷基”是指具有至少一个杂原子并具有两个或多个连接点位的由脂肪烃形成的基团。
术语“烯基”是指具有一根或多根碳-碳双键、具有一个连接点位的由烃形成的基团,该基团可以是未取代的或者是取代的。
术语“炔基”是指具有一根或多根碳-碳三键、具有一个连接点位的由烃形成的基团,该基团可以是未取代的或者是取代的。
术语“亚烯基”是指具有一根或多根碳-碳双键、具有两个或多个连接点位的由烃形成的基团,该基团可以是未取代的或者是取代的。
术语“亚炔基”是指具有一根或多根碳-碳三键、具有两个或多个连接点位的由烃形成的基团,该基团可以是未取代的或者是取代的。
术语“杂烯基”、“亚杂烯基”、“杂炔基”、“亚杂炔基”是指具有一个或多个杂原子的类似基团。
术语“芳基”是指具有一个连接点位、由芳香烃形成的基团,该基团可以是未取代的或者是取代的。
术语“杂芳基”是指具有至少一个杂原子并具有一个连接点位的由芳香基团形成的基团,该基团可以是未取代的或者是取代的。
术语“芳烷基”是指具有一个芳基取代基的烷基形成的基团,该基团可以进一步被取代或未取代。
术语“杂芳烷基”是指具有杂芳基取代基的烷基形成的基团,该基团可进一步被取代或未取代。
术语“亚芳基”是指由芳香烃形成的具有两个连接点位的基团,该基团可以是未取代的或者是取代的。
术语“亚杂芳基”是指由具有至少一个杂原子和具有两个连接点位的芳基形成的基团,该基团可以是未取代的或者是取代的。
术语“亚芳基亚烷基”是指具有芳基和烷基的基团,它在烷基上具有一个连接点位,在芳基上具有一个连接点位。
术语“杂亚芳基亚烷基”是指具有芳基和烷基的基团,它在芳基上具有一个连接点位,在烷基上具有一个连接点位,并至少具有一个杂原子。除非另有说明,否则所有基团均可以是未取代的或者是取代的。
短语“相邻”在用于限定一个器件中的层时并不一定指一层与另一层紧邻。另一方面,短语“相邻的R基团”是指在一个化学通式中相互邻近的多个R基团(即多个R基团位于通过化学键连接的原子上)。
术语“化合物”是指由分子形成的不带电物质,所述分子由原子组成,所述原子不能通过物理方法分离。
术语“配位体”是指附着在金属离子配位层上的分子、离子或原子。
术语“配合物”作为名词时是指具有至少一个金属离子和至少一个配位体的化合物。
术语“环金属化的配合物”是指一种配合物,其中一个有机配位体至少在两个位置与一个金属相连,形成环状的金属配位结构,并且至少有一个连接点具有金属-碳键。另外,在本文中使用IUPAC编号系统,其中周期表的族由左至右编号为1-18(CRC化学物理手册,第81版,2000)。
除非另有说明,否则本文使用的所有技术和科学术语的含义与本领域普通技术人员通常认知的术语具有相同的含义。除非另有说明,否则附图中的所有字母符号代表具有该原子缩写的原子。尽管在本发明实践或试验中可使用与本文所述的方法和材料相似或等同的方法或材料,但是合适的方法和材料描述如下。本文提到的所有出版物、专利申请、专利和其它参考文献均在此全文引为参考。在发生矛盾时,以本说明书,包括定义为准。另外,所述材料、方法和实施例是说明性的而非限定性的。
由下列详细描述和权利要求书可显示本发明的其它特征和优点。
附图说明
图1是发光二极管(LED)的示意图;
图2是发光二极管能级示意图;
图3显示通式I(a)-I(e)的场致发光铱配合物;
图4是式II的电子迁移组分;
图5是通式II(a)-II(i)的电子迁移组分;
图6是通式III(a)、III(b)的电子迁移组分;
图7是式IV(a)-IV(h)的多齿连接基团;
图8是式IV电子迁移组分;
图9是式IV(a)-IV(ag)电子迁移组分;
图10是式VI电子迁移组分;
图11显示通式VI(a)-VI(m)电子迁移组分;
图12显示式VII电子迁移组分;
图13显示已知的电子迁移组分的通式;
图14是发光二极管试验器件的示意图;
图15是使用铱配合物I(a)的场致发光效率图;
图16是使用铱配合物I(b)的场致发光效率图;
图17是对于不同的铱配合物发射体的最佳ET/AQ组成曲线图;
图18是铱配合物发射体的LUMO对ET/AQ组成的LUMO的曲线图。
较好实例的详细描述
本发明涉及一种电子器件,在两个电极之间它包括至少一层电子迁移和/或抗淬灭层和一层光活性层。图1所示的器件100具有阳极层110和阴极层160。与阳极层相邻的是包括空穴迁移材料的层120。与阴极层相邻的是包括电子迁移和/或抗淬灭材料的层140。在迁移空穴迁移层和电子迁移和/或抗淬灭层之间的是光活性层130。在靠近阴极处所述器件还通常任选地使用另一层电子迁移层150。层120、130、140和150可各自和共同地被称为活性层。
根据器件100的用途,所述光活性层130可以是通过施加电压来激活的发光层(例如在发光二极管或发光电化学电池中的发光层),通过施加或不施加偏压能够响应辐射能并产生信号的材料的层(例如光检测器)。光检测器的例子包括光导电池、光敏电阻、光开关、光晶体管和光电管,以及光伏电池(参见Markus,John,Electronics and Nucleonics Directionary,470和476(McGraw-Hill,Inc.1966))。在本发明范围内的器件可以是如上所述的发光二极管、发光场致发光器件或者是光检测器。
图2是将用于下面讨论的器件力能学示意图。所有的能级均以能量定义为零的真空能级117为基准。因此,它们均为负值。将ET/AQ层的最低未占据分子轨道(LUMO)的能级定义为E1。将光活性层的LUMO定义为E2。将阴极的功函定义为E3,将光活性层的最高占据分子轨道(HOMO)的能级定义为E4,将ET/AQ层的HOMO定义为E5。最高能量是指能级接近真空能级。这些能级可使用例如光电子能谱法在固体状态测定。还可在溶液中使用循环伏安法测量分子的相对能级。
在场致发光器件中一种有效的电子迁移和/或抗淬灭(ET/AQ)材料必须具有下列性能:
1.该材料必须能有效迁移电子,迁移率较好>10-7cm2/(V·sec);
2.ET/AQ材料的LUMO与阴极的功函之间的能级差必须足够小,以便由阴极有效地注入电子。能垒较好低于1V,即E1-E3<1V;
3.ET/AQ材料的LUMO必须足够高,以阻止其接纳来自光活性层的电子。这通常要求E1-E2>-1V,较好E1-E2>0;
4.ET/AQ材料的HOMO能级必须足够小,以阻止其向光活性层提供电子。这通常要求E4-E5>-1V,较好E4-E5>0。
在上述标准3和4中的ET/AQ材料的最佳能级可由电子转移理论决定。电子转移反应的速度和能量差之间的关系可参见Marcus理论(R.A.Marcus、P.Siders,J.Phys.Chem.,86,622(1982))。在其最简单的形式中,它表示为:
k=νexp[-(Ef-Ei+λ)2/4λkBT] (1)
其中,k是速度常数;kB是Boltzman常数;T是温度;Ei和Ef是初始和最终态的能量;λ称为重组能量,它是一个现象参数,表示初始和最终态电子振动相互作用的集合效应;前因子ν包括波动函数重叠积分α,并且现象学地由下式(取决于电荷分开距离r)表示:
ν(r)=ν0exp[-α(r-r0)] (2)
前因子ν0通常约为1013sec-1.
最终态(即电荷分开的状态)的能量取决于电子和空穴的分开距离r以及施加的电场E0。它可表示为:
Ef=Ef ∞-e2/(εr)-E0z (3)
其中,Ef ∞是在没有外部电场并且电子和空穴相距无穷远时的电荷分开状态的能量;ε是介质的介电常数;z是施加电场的方向。在施加的电场和各种电子-空穴距离下计算电子转移速度的方法可参见前面提到的Wang和Suna的J.Phys.Chem.,101,5627-5638(1997)。
在标准3中,为了防止发生明显的电子迁移淬灭,ET/AQ层的LUMO能级应高得足以使由光活性层向ET/AQ层的电子迁移速度明显低于激发子的激发态辐射衰变速度。因此,LUMO能级的最佳值取决于所涉及的电子转移反应的重组能量λ和重叠积分α以及光活性层激发子的辐射寿命。通常,要求E1-E2>-1V,较好E1-E2>0。
在标准4,同样ET/AQ层的HOMO能级应低得足以使由ET/AQ层向发光层的电子转移速度明显低于激发子的激发态辐射衰变速度。HOMO能级的最佳值取决于所涉及的电子转移反应的重组能量λ和重叠积分α以及光活性层激发子的辐射寿命。通常,要求E4-E5>-1V,较好E4-E5>0。
因此,对于给定的光活性材料,存在一种最佳的EQ/AT材料,它能满足标准1-4的要求。对于一系列结构相似的ET/AQ材料(重组能和重叠积分期望相同),期望在器件效率和ET/AQ材料的LUMO能量之间找到一个关联。对于给定的光活性材料,应该具有ET/AQ材料的LUMO能量的最佳范围,此时可获得最大的效率。
还应理解所述ET/AQ材料必须与使用的光活性材料化学相容。例如,当沉积在光活性材料层上时,ET/AQ材料必须形成光滑的膜。如果发生团聚,器件的性能将下降。可使用显微学和光谱学上已知的各种技术探测发生的团聚。
所述器件上的其它各层可以使用已知适合这些层的任何材料制得。阳极110是对注入正电荷载流子特别有效的电极。它可以由例如含金属、混合金属、合金、金属氧化物或混合金属氧化物的材料制得,或它可以是导电聚合物,或它们的混合物。合适的金属包括第11族的金属、第4、5、6族的金属和第8-10族的过渡金属。如果要求阳极是透光的,则一般使用第12、13和14族的混合金属氧化物,例如氧化铟锡。阳极110还可包括有机材料,例如聚苯胺(参见“Flexiblelight-emitting diodes made from soluble conducting polymer”,Nature Vol.357,pp477-479(1992年6月11日))。阳极和阴极中应至少有一个是至少部分透明的,以观察产生的光线。
适合作为层120的空穴迁移材料的例子概述在例如Y.Wang的Kirk-OthmerEncyclopedia of Chemical Technology,第4版,18卷,p837-860,1996。可使用空穴迁移分子和聚合物。Petrov等在公开号为WO 02/02714的PCT申请中公开了化合物二(4-N,N-二乙基氨基-2-甲基苯基)-4-甲基苯基甲烷(MPMP)适合作为空穴迁移组分。常用的空穴迁移分子有N,N’-二苯基-N,N’-二(3-甲基苯基)-[1,1’-联苯]-4,4’-二胺(TPD)、1,1-二[(二-4-甲苯基氨基)苯基]环己烷(TAPC)、N,N’-二(4-甲基苯基)-N,N’-二(4-乙基苯基)-[1,1’-(3,3’-二甲基)联苯]-4,4’-二胺(ETPD)、四(3-甲基苯基)-N,N,N’,N’-2,5-苯二胺(PDA)、α-苯基-4-N,N-二苯基氨基苯乙烯(TPS)、对-(二乙基氨基)苯甲醛二苯基腙(DEH)、三苯胺(TPA)、二[4-(N,N-二乙基氨基)-2-甲基苯基](4-甲基苯基)甲烷(MPMP)、1-苯基-3-[对(二乙基氨基)苯乙烯基]-5-[对(二乙基氨基)苯基]二氢吡唑(PPR或DEASP)、1,2-反式-二(9H-咔唑-9-基)环丁烷(DCZB)、N,N,N’,N’-四(4-甲基苯基)-(1,1’-联苯)-4,4’-二胺(TTB)以及卟啉化合物,例如酞菁铜。常用的空穴迁移聚合物是聚乙烯基咔唑、(苯甲基)聚硅烷和聚苯胺及其混合物。还可通过将例如上述的空穴迁移分子掺杂至聚合物(例如聚苯乙烯和聚碳酸酯)中制得空穴迁移聚合物。
光活性层130的例子包括所有已知的场致发光材料。较好是有机金属场致发光材料。最好的化合物包括环金属化的铱和铂场致发光化合物及其混合物。铱与苯基吡啶、苯基喹啉或苯基嘧啶配体的配合物公开在Petrov等的PCT公开申请WO 02/02714中作为场致发光化合物。其它有机金属配合物可参见例如US2001/0019782、EP 1191612、WO02/15645和EP 1191614。带有掺杂铱金属配合物的聚乙烯基咔唑(PVK)活性层的场致发光器件可参见Burrows和Thompson的PCT WO 00/70655和WO 01/41512。包括电荷载带受体材料和磷光铂配合物的场致发光发射层可参见Thompson等的US 6,303,238、Bradley等的Synth.Met.(2001),116(1-3),379-383和Campbell等的Phys.Rev.B.Vol.65 085210。几种合适的铱配合物的例子可参见图3的式I(a)-I(e)。也可使用类似的四齿铂配合物。这些场致发光配合物可以单独使用或者如上所述掺杂在电荷迁移受体中。
一种ET/AQ材料是菲咯啉衍生物,该菲咯啉衍生物可具有图4所示的通式II,其中:
R1和R2可相同或不同,各自选自H、F、Cl、Br、烷基、杂烷基、烯基、炔基、芳基、杂芳基、CnHaFb、OCnHaFb、C6HcFd和OC6HcFd;
a、b、c和d为0或整数,使得a+b=2n+1,c+d=5;
n是整数;
x是0或1-3的整数;
y是0、1或2;
条件是在芳环上具有至少一个选自F、CnHaFb、OCnHaFb、C6HcFd和OC6HcFd的取代基。
这种菲咯啉的具体例子有图5的式II(a)-II(i)。
所述菲咯啉衍生物可具有图6所示的式III(a)或III(b),其中:
R1、R2、a-d、n和x如上所述;
R3可相同或不同,各自选自单键和选自亚烷基、杂亚烷基、亚芳基、亚杂芳基、亚芳基亚烷基和杂亚芳基亚烷基的基团;
Q选自单键和多价基团;
m是至少等于2的整数;
p是0或1。
多价Q基团的例子示于图7的式IV(a)-IV(h)。
另一种ET/AQ材料是喹喔啉衍生物。该喹喔啉衍生物可具有图8所示的通式V,其中:
R4和R5可相同或不同,各自选自H、F、Cl、Br、烷基、杂烷基、烯基、炔基、芳基、杂芳基、亚烷基芳基、烯基芳基、炔基芳基、亚烷基杂芳基、烯基杂芳基、炔基杂芳基、CnHaFb、OCnHaFb、C6HcFd和OC6HcFd;或者两个R5基团一起形成一个亚芳基或亚杂芳基;
a、b、c和d为0或整数,使得a+b=2n+1,c+d=5;
n是整数;
w是0或1-4的整数。
该通式喹喔啉的具体例子可参见图9的式V(a)-V(ag)。
所述喹喔啉可具有图10的通式VI,其中:
R4、R5、a-d和n如上所述;
R3可相同或不同,各自选自单键和选自亚烷基、杂亚烷基、亚芳基、亚杂芳基、亚芳基亚烷基和杂亚芳基亚烷基的基团;
Q选自单键和多价基团;
m是至少等于2的整数;
p是0或1;
w是0或1-4的整数。
Q基团的例子如上所述。该通式的喹喔啉的具体例子有图11所示的通式VI(a)-VI(m)。
所述喹喔啉可具有图12的通式VII,其中的R3、R4、R5、Q、a-d、m、n、p和w如上所述。
可用于层150的其它电子迁移材料的例子包括金属鳌合的8-羟基喹啉类化合物,例如三(8-羟基喹啉)合铝(Alq3),和唑(azole)化合物,例如2-(4-联苯基)-5-(4-叔丁基苯基)-1,3,4-噁二唑(PBD)和3-(4-联苯基)-4-苯基-5-(4-叔丁基苯基)-1,2,4-三唑(TAZ)及其混合物。
阴极160是对于注入电子或负载流子特别有效的电极。阴极可以是功函低于阳极的任何金属或非金属。阴极材料可选自第一族碱金属(例如Li、Cs)、第二族金属(碱土金属)、第12族金属,包括稀土元素和镧系和锕系元素。可使用例如铝、铟、钙、钡、钐和镁及其混合材料。还可将含锂有机金属化合物、LiF、Li2O沉积在有机层和阴极层之间以降低运行电压。
在有机电子器件中已知还有其它层。例如,在阳极110和空穴迁移层120之间还可具有一层(未显示)用于促进正电荷迁移和/或层间带隙匹配,或者作为保护层的层,可使用本领域已知的层。另外,上述各层的任何一层可以由两层或多层组成。或者,可对阳极层110、空穴迁移层120、电子迁移层140和150以及阴极层160中的一部分或全部进行表面处理以提高载流子迁移效率。各组分层材料的选择较好兼顾提供高效器件的目的。
可以理解各功能层可由多于一层的层形成。
所述器件可由多种技术制得,包括将各层依次蒸气沉积在合适的基片上。可使用的基片有例如玻璃和聚合物膜。可使用常规的蒸气沉积技术,例如热蒸发、化学气相沉积等。或者,可使用任何常规的涂覆或印刷技术,包括但不限于旋转涂覆、蘸涂、辊对辊技术、喷墨打印、网印和凹槽辊印刷由合适的溶剂中的溶液或分散液涂覆有机层。一般来说,各层可具有下列厚度范围:阳极110:500-5000,较好1000-2000;空穴迁移层120:50-2000,较好200-1000;光活性层130:10-2000,较好100-1000;电子迁移层140和150:50-2000,较好100-1000;阴极160:200-10000,较好300-5000。各层的相对厚度可影响器件中的电子-空穴复合区,从而影响器件的发射光谱。因此应选择电子迁移层的厚度使得电子-空穴复合区在发光层中。所需的层厚比例将取决于所用材料的实际性能。
实施例
下列实施例说明本发明的一些特征和优点。它们用于说明而非限定本发明。除非另有说明,否则所有的百分数均是重量百分数。
实施例1-17
本实施例说明制造某些ET/AQ组分:
实施例1
本实施例说明制备图9的化合物V(b).
将3,4-二氨基甲苯(28.78g,0.236mol)和苯偶酰(45g,0.214mol)的混合物在738ml氯仿中与2.16ml三氟乙酸一起回流3小时。混合物用10%HCl、盐水洗涤三次,硫酸镁干燥,过滤,随后用二氧化硅床真空过滤。将形成的溶液蒸发至干。在550ml甲醇中重结晶69g粗产物,在50℃的真空烘箱中将滤得的固体干燥1小时,得到55.56g干固体,产率78.8%。
实施例2
本实施例说明制备图9的化合物V(e)。
将3.4-二氨基甲苯(4.49g,0.037mol)和4,4’-二甲氧基苯偶酰(9.46g,0.035mol)的混合物在125ml氯仿中与0.35ml三氟乙酸一起回流6小时。混合物用水洗涤二次,硫酸镁干燥,蒸发至约11克。将固体溶解在1∶1的乙酸乙酯∶氯仿,用快速色谱法分离,以乙酸乙酯洗脱。蒸发后获得9.7g黑色固体,72%产率。
实施例3
本实施例说明制备图9的化合物V(d)。
将3,4-二氨基甲苯(5.36g,44mmol)和菲醌(8.33g,0.040mol)的混合物在119ml氯仿中与0.4ml三氟乙酸一起回流6小时。用中号玻璃砂芯过滤混合物并在430g甲乙酮中重结晶,得到5.5g绒毛状黄色产物,产率为46%。
实施例4
本实施例说明制备图10的化合物V(f)。
将3,4-二氨基甲苯(5.36g,44mmol)和2,2’-吡啶偶酰(Pyridil)(8.49g,40mmol)的混合物在119ml氯仿中与0.4ml三氟乙酸一起回流4小时。分离反应混合物并用100ml水洗涤四次,蒸发至10.4g。将形成的固体溶解在1∶1乙酸乙酯∶氯仿。快速色谱法纯化,用乙酸乙酯洗脱。蒸发后得到9.3g固体。
实施例5
本实施例说明制备图10的化合物V(g)。
将3,4-二氨基苯甲酸甲酯(7.28g,44mmol)和苯偶酰(8.41g,40mmol)的混合物在140ml二氯甲烷中回流21小时。将反应混合物蒸发至干,随后溶解在520ml甲醇和150ml二氯甲烷中回流。随后将溶液部分蒸发至选择性结晶所需产物。
实施例6
本实施例说明制备图10的化合物V(k)。
将3,4-二氨基苯甲酸甲酯(6.37g,0.038mol)和4,4’-二甲氧基苯偶酰(9.46g,0.035mol)的混合物在142ml二氯甲烷中与三滴三氟乙酸一起回流5小时。加入10.7g N-甲基吡咯烷酮并再回流26小时。混合物用水洗涤三次、硫酸镁干燥、过滤并随后沉淀,将产物慢慢倾注在550g甲醇中。静止过夜后,过滤产物,在95℃的真空中干燥后得到10.39g产物。
实施例7
本实施例说明制备图10的化合物V(r)。
将3,4-二氨基苯甲酸甲酯(6.12g,0.037mol)和菲醌(7.08g,0.034mol)的混合物在119ml二氯甲烷中回流5小时。加入100克N-甲基吡咯烷酮,随后蒸去氯化物溶剂。将反应容器加热至150℃,得到一透明溶液,并且用气相色谱法监测该反应。将混合物倒入410g甲醇中沉淀产物,滤处固体沉淀。在甲苯中重结晶产物,并在1200g甲乙酮、150g甲苯和1100g四氢呋喃的混合液中再次重结晶,得到3.3g珠光金色毛状产物。
实施例8
本实施例说明制备图10的化合物V(I)。
将1,2-苯二胺(13.91g,0.129mol)和4,4’-二溴苯偶酰(45g,0.116mol)的混合物在558ml氯仿中与1.0ml三氟乙酸一起回流6小时。混合物用10%盐酸洗涤三次,蒸发至约51克。由600ml乙酸乙酯和100ml甲醇中回流重结晶。过夜后形成大晶体,过滤、用甲醇洗涤两次并干燥至29.63g,其中4.9g来自冷却的母液。
实施例9
本实施例说明制备图10的化合物V(h)。
将2,3-二氨基甲苯(4.84g,0.040mol)和苯偶酰(7.56g,0.036mol)的混合物在112ml二氯甲烷中回流19小时。混合物用12%盐酸洗涤四次,硫酸镁干燥,过滤并蒸发,得到约9.5g棕色固体。在回流下将固体溶解在495g甲醇中,蒸去约300g溶剂。用冰冷却后得到细微的晶体。过滤并用甲醇洗涤晶体滤饼。
实施例10
本实施例说明制备图9的化合物V(i)。
将2,3-二氨基甲苯(5.05g,0.041mol)和菲醌(7.84g,0.038mol)的混合物在112ml氯仿中回流29小时。将形成的溶液淋洗在硅胶色谱柱并用氯仿洗脱。蒸去溶剂得到约10g产物,随后用真空烘箱干燥。产物出现结晶。
实施例11
本实施例说明制备图9化合物V(j)。
将3,4-二氨基苯甲酸甲酯(7.28g,0.044mol)和2,2’-吡啶偶酰(8.48g,0.040mol)的混合物在140ml二氯甲烷中回流7小时。将溶液蒸发至15.7g,在回流下将该固体溶解在240ml二氯甲烷和140ml甲醇中。加入280ml甲醇并蒸去约150ml溶剂,将溶液静置过夜。收集形成的固体并干燥至9.8g。取7.7g产物溶解在203g甲醇和50g二氯甲烷中。蒸去超过50ml的溶剂。过夜后形成晶体。过滤并在真空烘箱中干燥之。
实施例12
本实施例说明制备图9的化合物VI(a)。
将3,3-二氨基联苯胺(0.4580g,2.14mmol)和1,10-菲咯啉-5,6-二酮(0.9458g,4.5mmol)的混合物在10g N-甲基吡咯烷酮中与0.045ml三氟乙酸一起在85℃加热23小时。在环境温度向反应容器中加入氯仿,用细玻璃砂芯过滤之,丙酮和二乙醚洗涤,随后在90℃真空下干燥。
实施例13
本实施例说明制备图5的化合物II(c)。
将2,9-二碘-1,10-菲咯啉(900mg,2.08mmol,根据Toyota等的TetrahedronLetters 1998,39,2697-2700制得)、3-三氟甲基苯硼酸(989mg,5.20mmol,Aldrich Chemical Company,Milwaukee,WI)、四(三苯膦)合钯(481mg,0.416mmol,Aldrich Chemical Company)和碳酸钠(882mg,8.32mmol)的混合物在水(20ml)/甲苯(50ml)中在氮气中回流15小时。分离有机层,水相用3×25ml氯仿萃取。合并有机层,硫酸钠干燥并蒸发至干。快速硅胶色谱法纯化,用己烷/二氯甲烷(1∶1,v/v)作为洗脱液(产物Rf=0.25),得到所需的产物,为浅黄色固体(560mg,57%),1H NMR测定的纯度超过95%。
1H NMR(CDCl3,300MHz,296K):δ 8.81(s,2H),8.63(d,2H,J=7.5Hz),8.36(d,2H,J=8.4Hz),8.19(d,2H,J=8.41Hz),7.84(s,2H),7.68-7.77(m,6H)ppm.19F NMR(CDCl3,282 MHz,296K)δ-63.25ppm.
使用类似的方法制得化合物II(a)、II(g)、II(h)和II(i)。
实施例14
本实施例说明制备图5的化合物II(b)。
使用与实施例13相同的方法,采用3,8-二溴-1,10-菲咯啉(1.5g,4.4mmol,根据Saitoh等Canadian Journal of Chemistry 1997,75,1336-1339制得)、4-三氟甲基苯硼酸(2.11g,11.1mmol,Lancaster Chemical Company,Windham,NH)、四(三苯膦)合钯(513mg,0.444mmol)和碳酸钠(1.41g,13.3mmol)、水(20ml)和甲苯(100ml),用快速硅胶柱色谱法(二氯甲烷/甲醇,9:v∶v)纯化,随后用冷甲醇洗涤之,得到白色固体(520mg,25%),1H NMR测定的纯度超过95%。
1H NMR.1H NMR(CDCl3,300MHz,296K):δ9.46(d,2H,J=2.3Hz),8.45(d,2H,2.3Hz),7.94(s,2H),7.91(d,4H,J=8.3Hz),7.82(d,4H,J=8.4Hz)ppm.19F NMR(CDCl3,282MHz,296 K)δ-63.12ppm.
实施例15
本实施例说明制备图5的化合物II(e)。
将2,9-二碘-1,10-菲咯啉(1.00g,2.31mmol)、4-氟苯硼酸(972mg,6.96mmol)、二(二苯膦基)丁烷(92mg,0.213mmol,Aldrich)、乙酸钯(52mg,0.23mmol,Aldrich)和氟化钠(810mg,13.9mmol,Aldrich)在无水二噁烷(100ml)中回流15小时。在减压下除去二噁烷,如实施例1所述对粗产物进行水性溶液处理。用快速硅胶色谱法纯化(100%二氯甲烷,产物Rf=0.57),得到浅黄色固体(567mg,67%),1H NMR测定的纯度超过95%。
1H NMR.1H NMR(CDCl3,300MHz,296K):δ8.43(dd,4H,JHH=10.4Hz,JHF=5.5Hz),8.28(d,2H,J=8.4Hz),7.77(s,2H),7.26(dd,4H,JHH=9.9Hz,JHF=5.9Hz)ppm.19F NMR(CDCl3,282MHz,296K)δ-113.0ppm.
实施例16
本实施例说明制备图5的化合物II(d)。
使用与实施例13和14相同的方法,采用4,7-二氯-1,10-菲咯啉(300mg,1.2mmol,根据J.Heterocyclic Chemistry 1983,20,681-6制得)、3,5-二(三氟甲基)苯硼酸(0.930g,3.650mmol,Aldrich)、二(二苯膦基)丁烷(154mg,0.361mmol)、乙酸钯(81mg,0.361mmol)和碳酸钠(0.510g,9.62mmol)、水(5ml)和甲苯(30ml),得到所需的白色固体产物(410mg,56%)。
1H NMR(CDCl3,300MHz,296K):δ9.35(d,2H,J=4.49Hz),8.06(s,2H),8.00(s,4H),7.73(2H,s),7.66(d,2H,J=4.52Hz)ppm.19F NMR(CDCl3,282MHz,296K)δ-63.32ppm.
实施例17
本实施例说明制备图5的化合物II(f)。
使用与实施例15相同的方法,采用2,9-二氯-1,10-菲咯啉(1.0g,4.01mmol,根据Yamada等的Bulletin of the Chemical Society of Japan 1990,63,2710-12制得)、3,5-二(三氟甲基)苯硼酸(2.59g,10.0mmol)、二(二苯膦基)丁烷(171mg,0.401mmol)、乙酸钯(90mg,0.401mmol)和氟化钾(1.40g,24.1mmol)和无水二噁烷(100ml)。用二乙醚洗涤粗产物来纯化产物,得到所需的白色固体产物(345mg,14%)。
1H NMR(CDCl3,300MHz,296K):δ8.92(d,4H,JHF=1.46Hz),8.45(d,2H,J=8.3Hz),8.25(d,2H,J=8.5Hz),8.02(s,2H),7.91(s,2H)ppm.19F NMR(CDCl3,282MHz,296K)δ-63.50ppm.
所述电子迁移和/或抗淬灭组分的性能列于下表1。已知的ET/AQ化合物A和B示于图13。
表1性能
化合物 | 发生吸收(nm)E1-E5 | 最大吸收(nm) | E1/2对SCE(V) | LUMO对真空(eV)E1 |
II(b) | 382 | 318 | -1.56 | -3.28 |
II(a) | 376 | 320 | -1.77 | -3.07 |
II(c) | 368 | 342 | -1.68 | -3.16 |
II(d) | 362 | 310 | -1.54 | -3.3 |
II(e) | 372 | 342 | -1.8 | -3.04 |
II(f) | 370 | 342 | -1.52 | -3.32 |
V(a) | 375 | 345 | -1.5 | -3.33 |
V(b) | 378 | 339 | -1.6 | -3.24 |
V(c) | 400 | 385 | -1.17 | -3.67 |
V(d) | 410 | 397 | -1.3 | -3.54 |
V(g) | 390 | 352 | -1.29 | -3.55 |
V(a) | - | - | - | - |
V(e) | 405 | 369 | -1.66 | -3.18 |
V(f) | 378 | 339 | -1.53 | -3.31 |
V(k) | 420 | 382 | -1.35 | -3.49 |
V(i) | 407 | 394 | -1.28 | -3.56 |
v(h) | 385 | 343 | -1.59 | -3.25 |
v(r) | 417 | 401 | -1.03 | -3.81 |
V(l) | 380 | 347 | -1.49 | -3.35 |
V(j) | 380 | 342 | -1.22 | -3.62 |
化合物ADDPA | 368 | 310 | -1.85 | -2.99 |
化合物BDPA | 366 | 316 | -1.95 | -2.89 |
实施例18
本实施例说明制备图3式I(a)所示的铱场致发光配合物。
苯基吡啶配位体,2-(4-氟苯基)-5-三氟甲基吡啶
使用的总体方法描述在O.Lohse、P.Thevenin、E.Waldvogel Synlett 1999,45-48。将200ml经脱气的水、20g碳酸钾、150ml 1,2-二甲氧基乙烷、0.5gPd(PPh3)4、0.05mmol 2-氯-5-三氟甲基吡啶和0.05mol 4-氟苯基硼酸的混合物回流(80-90℃)16-30小时。用300ml水稀释形成的反应混合物并用二氯甲烷(2×100ml)萃取。合并的有机层用硫酸镁干燥,真空除去溶剂。通过真空分馏纯化液体产物。在己烷中重结晶固态产物。分离材料的纯度大于98%。
铱配合物
在氮气流中边将温度缓慢(30分钟)上升至185℃(油浴)边搅拌IrCl3·nH2O(54%Ir,508mg)、2-(4-氟苯基)-5-三氟甲基吡啶(由上面制得,2.20g)、AgOCOCF3(1.01g)和水(1ml)的混合物。在185-190℃2小时后,该混合物固化。将混合物冷却至室温。用二氯甲烷萃取该固体至萃取液无色。用短二氧化硅柱过滤合并的二氯甲烷溶液并蒸发。向残余物中加入甲醇(50ml)以后,将烧瓶在-10℃保持过夜。分离三环金属化的配合物黄色沉淀(化合物b),用甲醇洗涤,并真空干燥。得到1.07g产物(82%)。通过其在1,2-二氯乙烷中的热溶液缓慢冷却得到该配合物的X-射线X射线品质的晶体。
使用类似的方法制得铱配合物I(c)。
实施例19
本实施例说明制备图3通式I(d)所示的铱场致发光配合物。
配位体,2-(2-噻吩基)-5-(三氟甲基)吡啶
在氮气中将2-噻吩基硼酸(Lancaster Synthesis,Inc.,1.00g,7.81mmol)、2-氯-5-三氟甲基吡啶(Sldrich Chemical Co.,1.417g,7.81mmol)、四(三苯膦)合钯(O)(Aldrich,451mg,0.391mmol)、碳酸钾(EM Science,3.24g,23.4mmol)、水(20ml)和二甲氧基乙烷(Aldrich,20ml)搅拌回流20小时。将混合物冷却至室温并将有机层和水层分离。用3×50ml二乙醚萃取水层,合并的有机相用硫酸钠干燥、过滤,并将滤液蒸发至干。用快速硅胶色谱法纯化该粗产物,用CH2Cl2/己烷(1∶1)作为洗脱液(产品Rf=0.5),得到白色晶状固体产物(5.2g,分离的产率为73%)。
1H NMR(CDCl3,296Ki 300MHz):δ=7.73-7.57(2H,m),7.55(1H,d,J=8.5Hz),7.34(1H,d,J=4.8Hz),6.88(1H,d,J=4.8Hz)ppm.19F NMR(CDCl3,296K,282MHz)δ=-62.78ppm.
{IrCl[2-(2-噻吩基)-5-(三氟甲基)吡啶]2}2
在氮气中将上述2-(2-噻吩基)-5-(三氟甲基)吡啶(555mg,2.42mmol)、三氯化铱(Strem Chemicals,401mg,1.13mmol)、2-乙氧基乙醇(Aldrich Chemical Co.,10ml)和水(1ml)回流15小时。随后将反应混合物冷却至室温。过滤收集形成的沉淀产物,己烷洗涤,真空干燥得到575mg(37%)红橙色固体产物。
1HNMR(CDCl3,296K,300MHz):δ=9.30(4H,d,J=1.5Hz),7.80(4H,dd,J=2.0Hz and 8.5Hz),7.59(4H,d,J=8.5Hz),7.21(8H,d,J=4.8Hz),5.81(d,4H,J=4.9Hz).19F NMR(CDCl3,296K,282MHz)δ=-62.07ppm.
铱配合物{Ir[2-(2-噻吩基)-5-(三氟甲基)吡啶]3}:
在氮气中在170-180℃将上述{IrCl[2-(2-噻吩基)-5-(三氟甲基)吡啶]2}2(100mg,0.073mmol)、来自实施例1的2-(2-噻吩基)-5-(三氟甲基)吡啶(201mg,0.88mmol)和三氟乙酸银(Aldrich,40mg,0.18mmol)混合并搅拌10分钟。将混合物冷却至室温并将其再溶解在最少量的二氯甲烷中。使溶液通过硅胶柱,用二氯甲烷/己烷(1∶1)作为洗脱剂。收集首先洗脱的红橙色馏份(产品Rf=0.5),并蒸发至干。将残余物悬浮在己烷中,过滤沉淀的产物并用过量己烷洗涤至除去残留的2-(2-噻吩基)-5-(三氟甲基)吡啶,得到红橙色固体。分离的产物为50mg(39%)。
1H NMR(CDCl3,296K,300MHz):δ=7.73-7.57(6H,m),7.55(3H,d,J=8.5Hz),7.34(3H,d,J=4.8Hz),6.88(3H,d,J=4.8Hz).19F NMR(CDCl3,296K,282MHz)δ=-62.78.
实施例20
本实施例说明使用本发明电荷迁移组分形成有机发光二极管。
用热蒸发技术制得薄膜有机发光二极管器件,它包括空穴迁移层(HT层)、场致发光层(EL层)和至少一层电子迁移和/或抗淬灭层(ET/AQ层)。所有薄膜沉积的基本真空度为10-6乇。沉积室能在不中止真空的情况下沉积5种不同的薄膜。
使用购自Thin Film Devices,Inc.的带图案的氧化铟锡(ITO)涂覆玻璃基片。这些ITO是涂覆1400ITO涂层的康宁1737玻璃,片电阻为30Ω/平方,透光率80%。随后在洗涤剂水溶液中超声波清洗该带图案的ITO基片。该基片随后用蒸馏水、异丙醇漂清,在甲苯蒸气中脱脂约3小时。
接着将该清洁的带图案ITO基片装入真空室,并将该真空室抽真空至10-6乇。随后用氧等离子体将该基片进一步清洁约5-10分钟。清洁后,通过热沉积将多层薄膜依次沉积在该基片上。最后,通过掩模沉积Al或LiF和Al带图案的金属电极。在沉积过程中使用石英晶体监测器(Sycon STC-200)测量薄膜的厚度。实施例中所有给出的薄膜厚度均是标称的,假设沉积材料的密度为1算得的。随后从真空室中取出完成的有机发光二极管器件,不包装立即鉴定。
有机发光二极管样品的鉴定是测量其(1)电流-电压(I-V)曲线;(2)场致发光光度与电压的关系;(3)场致发光光谱与电压的关系。使用的设备200如图14所示。使用237、280型Keithley Source-Measurement Unit测量有机发光二极管样品220的I-V曲线。使用Minolta LS-110发光仪210测量场致发光光度(单位Cd/m2)与电压的关系,而使用Keithley SMU扫描电压。场致发光光谱是如下获得的:使用一对透镜230收集光线,使之透过电子快门240,经分光仪250分散,随后用二极管阵列探测器260测量。所有这三组测量均是同时进行的,并由计算机270控制。器件在某一电压下的效率是将LED的场致发光光度除以运行器件所需的电流密度得到的。单位为cd/A。
根据Appl.Phys.Lett,1999,75,4制得铱化合物XII(b)。不同的铱配合物的性能列于下表2。
表2 铱化合物的性能
EL化合物 | E1/2对SCE,V | HOMO对真空(eV)E4 | E1/2对SCE,V | 开始吸收(nm)E2-E4 | LUMO对真空(eV),E2 |
I(a) | 1.23 | -6.07 | -1.68 | 510 | -3.64 |
I(b) | 0.72 | -5.56 | -2.21 | 511 | -3.13 |
I(c) | 1.17 | -6.01 | -1.62 | 539.5 | -3.71 |
I(d) | 1.05 | -5.89 | -1.74 | 571 | 3.72 |
器件层和厚度总结于表3。在所有情况下,如上所述阳极为ITO、HT层为MPMP、阴极为厚600-800的Al。在某些情况下,存在第二ET层150。如表所示该层包括三(8-羟基喹啉)合铝(III)(Alq)或者二(2-甲基-8-羟基喹啉)(对苯基苯酚)合铝(III)(BAlq)。
还制得比较例a-d,它不使用ET/AQ层。这些比较例证明需要使用ET/AQ层来获得良好的性能。
比较例a2使用二苯甲酮作为ET/AQ层,它产生很差的器件性能。二苯甲酮是白色的,带隙超过EL化合物I(a)(它是黄色的)的带隙。此比较例证明在ET/AQ层中使用大带隙材料不足以阻断能量迁移。
比较例a3和a4使用化合物I(c)作为ET/AQ层,并使用Alq或BAlq为第二电子迁移层。尽管化合物I(c)是橙色的,带隙小于化合物I(a)(它是黄色的)的带隙,但是它能获得相对良好的器件性能。
表3
试样 | HT() | EL() | ET/AQ() | ET() |
比较例a | 523 | I(a)520 | ||
9-1 | 506 | I(a)430 | II(b)405 | |
9-2 | 507 | I(b)407 | 比较例A 408 | |
9-3 | 507 | I(a)405 | 比较例B 407 | |
9-4 | 505 | I(a)404 | II(a)305 | |
9-5 | 515 | I(a)407 | II(c)409 | |
9-6 | 508 | I(a)411 | II(h)416 | |
9-7 | 510 | I(a)408 | II(i)412 | |
9-8 | 516 | I(a)419 | II(d)406 | |
9-9 | 512 | I(a)434 | II(g)415 | |
9-10 | 505 | I(a)415 | II(e)432 | |
9-11 | 514 | I(a)402 | II(f)431 | |
9-12 | 545 | I(a)403 | V(a)430 | Alq 430 |
9-13 | 508 | I(a)625 | V(b)425 | |
9-14 | 509 | I(a)413 | V(c)416 | |
9-15 | 578 | I(a)411 | V(d)381 |
9-16 | 549 | I(a)425 | V(g)423 | |
9-17 | 533 | I(a)417 | VI(a)411 | |
9-18 | 527 | I(a)418 | V(e)418 | |
9-19 | 502 | I(a)403 | V(f)106 | Alq 303 |
9-20 | 505 | I(a)412 | V(k)439 | |
9-21 | 514 | I(a)416 | V(i)408 | |
9-22 | 513 | I(a)409 | V(h)414 | |
9-23 | 515 | I(a)500 | V(r)410 | |
9-24 | 516 | I(a)409 | V(l)432 | |
9-25 | 504 | I(a)412 | V(j)402 | |
比较例a2 | 507 | I(a)409 | 苯甲酮408 | |
比较例a3 | 519 | I(a)411 | I(c)110 | Alq 309 |
比较例a4 | 507 | I(a)413 | I(c)105 | BAlq 308 |
比较例b | 531 | I(b)500 | ||
9-26 | 512 | I(b)410 | 比较例A 406 | |
9-27 | 523 | I(b)402 | 比较例B 416 | |
比较例c | 510 | I(c)532 | ||
9-28 | 512 | I(c)415 | II(g)414 | |
9-29 | 516 | I(c)401 | II(b)408 | |
9-30 | 512 | I(c)413 | 比较例B 407 | |
9-31 | 545 | I(c)462 | 比较例A 111 | Alq 319 |
9-32 | 506 | I(c)403 | II(d)472 | |
9-33 | 503 | I(c)404 | 比较例A 406 | |
比较例d | 511 | I(d)508 | ||
9-34 | 504 | I(d)411 | 比较例B 418 | |
9-35 | 511 | I(d)418 | II(d)407 | |
9-36 | 512 | I(d)404 | II(g)402 | |
9-37 | 509 | I(d)409 | II(b)409 | |
9-38 | 516 | I(d)411 | II(a)406 |
如上所述对器件进行试验,结果列于下表4。
表4
试样 | 峰值辐射(cd/m2) | 峰值效率(cd/A) | 大致峰值波长(nm) |
比较例a | 在21V 4 | 0.01 | 525 |
9-1 | 在19V 3500 | 17 | 525 |
9-2 | 在22V 3000 | 10 | 525 |
9-3 | 在19V 4500 | 20 | 525 |
9-4 | 在20V 3500 | 11 | 525 |
9-5 | 在25V 1200 | 6 | 525 |
9-6 | 在24V 1900 | 8 | 525 |
9-7 | 在28V 1600 | 8.5 | 525 |
9-8 | 在25V 2200 | 16 | 525 |
9-9 | 在21V 400 | 11 | 525 |
9-10 | 在23V 1000 | 6 | 525 |
9-11 | 在27V 900 | 8.5 | 525 |
9-12 | 在20V 2300 | 5.4 | 525 |
9-13 | 在27V 2700 | 10 | 525 |
9-14 | 在15V 400 | 10 | 525 |
9-15 | 在22V 90 | 4.4 | 525 |
9-16 | 在23V 2000 | 13 | 525 |
9-17 | 在20V 80 | 0.01 | 525 |
9-18 | 在22V 200 | 1.1 | 525 |
9-19 | 在15V 7000 | 30 | 525 |
9-20 | 在22V 1600 | 1 1 | 525 |
9-21 | 在19V 300 | 2.6 | 525 |
9-22 | 在20V 1200 | 9.5 | 525 |
9-23 | 在26V 220 | 2.6 | 525 |
9-24 | 在22V 100 | 1.2 | 525 |
9-25 | 在25V 180 | 8.5 | 525 |
比较例a2 | 在21V 16 | 0.2 | 525 |
比较例a3 | 在22V 3000 | 7 | 525 |
比较例a4 | 在22V 750 | 7 | 525 |
比较例b | 在20V 160 | 0.1 | 522 |
9-26 | 在24V 700 | 4 | 522 |
9-27 | 在24V 130 | 1.8 | 522 |
比较例c | 在15V 30 | 0.1 | 560 |
9-28 | 在23V 2400 | 13 | 560 |
9-29 | 在20V 1400 | 6.5 | 560 |
9-30 | 在18V 2200 | 5.8 | 560 |
9-31 | 在20V 510 | 2.2 | 560 |
9-32 | 在22V 1700 | 10 | 560 |
9-33 | 在27V 2000 | 5 | 560 |
比较例d | 在20V 0.1 | 0.015 | |
9-34 | 在26V 190 | 1.5 | 570 |
9-35 | 在26V 30 | 1.1 | 570 |
9-36 | 在24V 200 | 2 | 570 |
9-37 | 在25V 50 | 0.8 | 570 |
9-38 | 在25V 430 | 2.5 | 570 |
峰值效率是器件中场致发光化合物的最佳指示值,它给出了为得到合适的光子输出值(光度)必须输入器件的电子数。这是一个非常重要的数据,它反映发光材料的固有的效率。对于实际应用它也是重要的,因为高的效率意味着需要较少的电子就能获得相同的光度,从而意味着较低的能耗。高效率器件还具有长的寿命,因为较高比例的注入电子被转化成光子,而非产生热量或产生不合需要的化学副反应。
由表4的比较例可见,不使用ET/AQ层形成的器件比使用ET/AQ层的器件具有更低的场致发光效率。同样,对于给定的光活性材料,不同的ET/AQ材料可获得不同的器件效率,尽管所有这些ET/AQ材料的带隙均高于发光激发子的能量。这表明为了防止发光激发子的淬灭,仅仅阻断能量迁移过程是不够的。还必须阻断电子迁移过程。这可透过标准1-4的方法实现。因此,为了获得最大的场致发光效率,对于表4所示的各种不同的场致发光材料至少存在有一种最佳的匹配的ET/AQ材料。
作为例子,发射体I(c)和I(d)的场致发光效率与ET/AQ化合物的LUMO能量关系分别图示于图15和图16。对于各种光活性材料,所述效率对于使用的ET/AQ化合物是十分敏感的,并且通过改变ET/AQ LUMO能量可找到最佳的ET/AQ化合物。图17给出了适合本文研究的所有发射体的最佳ET/AQ化合物。由此可见,在实验不确定度范围内,在ET/AQ化合物的LUMO和发射体的LUMO之间存在一个总的关联。当发射体的LUMO能量下降时,最佳ET/AQ材料的LUMO能量随之下降。图18给出了最佳ET/AQ化合物的LUMO(y)对相应的发射体的LUMO(x)的关系图。其数据可粗略滴满足线性方程y=2(±0.1)+0.273×x。
Claims (23)
1.一种光活性电子器件,它包括:
(a)一个阳极;
(b)一个阴极,所述阴极的功函能级为E3;
(c)在所述阳极和所述阴极之间的光活性层,所述光活性层包括过渡金属的环金属化的配合物,所述环金属化的配合物具有LUMO能级E2和HOMO能级E4;
(d)置于所述阴极和所述光活性层之间的电子迁移和/或抗淬灭层,所述电子迁移和/或抗淬灭层的LUMO能级为E1和HOMO能级为E5;
条件是:
(1)E1-E3<1V;
(2)E1-E2>-1V;
(3)E4-E5>-1V。
2.如权利要求1所述的器件,其特征在于E1-E2>0。
3.如权利要求1所述的器件,其特征在于E4-E5>0。
4.如权利要求1所述的器件,其特征在于所述电子迁移和/或抗淬灭层的电子迁移率至少为10-7cm2/(V·sec)。
5.如权利要求1所述的器件,其特征在于所述电子迁移和/或抗淬灭层包括菲咯啉衍生物。
6.如权利要求5所述的器件,其特征在于所述菲咯啉衍生物具有图4的通式II,其中:
R1和R2可相同或不同,各自选自H、F、Cl、Br、烷基、杂烷基、烯基、炔基、芳基、杂芳基、CnHaFb、OCnHaFb、C6HcFd和OC6HcFd;
a、b、c和d为0或整数,使得a+b=2n+1,c+d=5;
n是整数;
x是0或1-3的整数;
y是0、1或2;
条件是在芳环上具有至少一个选自F、CnHaFb、OCnHaFb、C6HcFd和OC6HcFd的取代基。
7.如权利要求6所述的器件,其特征在于n是1-12的整数。
8.如权利要求5所述的器件,其特征在于所述菲咯啉衍生物选自图5的式II(a)-II(i)。
9.如权利要求5所述的器件,其特征在于所述菲咯啉衍生物具有图6所示的式III(a),其中:
R1和R2可相同或不同,各自选自H、F、Cl、Br、烷基、杂烷基、烯基、炔基、芳基、杂芳基、CnHaFb、OCnHaFb、C6HcFd和OC6HcFd;
R3可相同或不同,各自选自单键和选自亚烷基、杂亚烷基、亚芳基、亚杂芳基、亚芳基亚烷基和杂亚芳基亚烷基的基团;
Q选自单键和多价基团;
m是至少等于2的整数;
p是0或1;
x是0或1-3的整数。
10.如权利要求9所述的器件,其特征在于m是2-10的整数;n是1-12的整数,条件是当Q是单键时,p为0。
11.如权利要求5所述的器件,其特征在于所述菲咯啉衍生物具有图6所示的式III(b),其中:
R1和R2可相同或不同,各自选自H、F、Cl、Br、烷基、杂烷基、烯基、炔基、芳基、杂芳基、CnHaFb、OCnHaFb、C6HcFd和OC6HcFd;
R3可相同或不同,各自选自单键和选自亚烷基、杂亚烷基、亚芳基、亚杂芳基、亚芳基亚烷基和杂亚芳基亚烷基的基团;
Q选自单键和多价基团;
m是至少等于2的整数;
p是0或1;
x是0或1-3的整数。
12.如权利要求1所述的器件,其特征在于所述电子迁移和/或抗淬灭层包括喹喔啉衍生物。
13.如权利要求12所述的器件,其特征在于所述喹喔啉衍生物具有图8所示的通式V,其中:
R4和R5可相同或不同,各自选自H、F、Cl、Br、烷基、杂烷基、烯基、炔基、芳基、杂芳基、亚烷基芳基、烯基芳基、炔基芳基、亚烷基杂芳基、烯基杂芳基、炔基杂芳基、CnHaFb、OCnHaFb、C6HcFd和OC6HcFd;或者两个R5基团一起形成一个亚芳基或杂亚芳基;
a、b、c和d为0或整数,使得a+b=2n+1,c+d=5;
n是整数;
w是0或1-4的整数。
14.如权利要求13所述的器件,其特征在于n是1-12的整数。
15.如权利要求12所述的器件,其特征在于所述喹喔啉衍生物选自图9的式V(a)、V(b)、V(d)-V(i)和V(k)-V(ag)。
16.如权利要求12所述的器件,其特征在于所述喹喔啉衍生物选自图9的通式V(c)和V(j)。
17.如权利要求12所述的器件,其特征在于所述喹喔啉衍生物具有图10的通式VI,其中:
R4和R5可相同或不同,各自选自H、F、Cl、Br、烷基、杂烷基、烯基、炔基、芳基、杂芳基、亚烷基芳基、烯基芳基、炔基芳基、亚烷基杂芳基、烯基杂芳基、炔基杂芳基、CnHaFb、OCnHaFb、C6HcFd和OC6HcFd;或者两个R5基团一起形成一个亚芳基或杂亚芳基;
R3可相同或不同,各自选自单键和选自亚烷基、杂亚烷基、亚芳基、亚杂芳基、亚芳基亚烷基和杂亚芳基亚烷基的基团;
Q选自单键和多价基团;
a、b、c和d为0或整数,使得a+b=2n+1,c+d=5;
m是至少等于2的整数;
n是整数;
p是0或1。
18.如权利要求17所述的器件,其特征在于m是2-10的整数,n是1-12的整数,p为0。
19.如权利要求12所述的器件,其特征在于所述喹喔啉衍生物选自图11所示的通式VI(b)-VI(g)和VI(i)-VI(k)。
20.如权利要求12所述的器件,其特征在于所述喹喔啉衍生物选自图11所示的通式VI(a)、VI(h)、VI(l)和VI(m)。
21.如权利要求12所述的器件,其特征在于所述喹喔啉衍生物具有图11所示的通式VI(m)。
22.如权利要求12所述的器件,其特征在于所述喹喔啉衍生物具有图12的通式VII,其中
R4和R5可相同或不同,各自选自H、F、Cl、Br、烷基、杂烷基、烯基、炔基、芳基、杂芳基、亚烷基芳基、烯基芳基、炔基芳基、亚烷基杂芳基、烯基杂芳基、炔基杂芳基、CnHaFb、OCnHaFb、C6HcFd和OC6HcFd;或者两个R5基团一起形成一个亚芳基或杂亚芳基;
R3可相同或不同,各自选自单键和选自亚烷基、杂亚烷基、亚芳基、亚杂芳基、亚芳基亚烷基和杂亚芳基亚烷基的基团;
Q选自单键和多价基团;
a、b、c和d为0或整数,使得a+b=2n+1,c+d=5;
m是至少等于2的整数;
n是整数;
p是0或1。
23.如权利要求1-22所述的器件,其特征在于所述器件是发光二极管、发光电化学电池或光检测器。
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