CN102471678B - 芴二聚体和三聚体及使用它们的光电设备 - Google Patents
芴二聚体和三聚体及使用它们的光电设备 Download PDFInfo
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- CN102471678B CN102471678B CN201080030202.0A CN201080030202A CN102471678B CN 102471678 B CN102471678 B CN 102471678B CN 201080030202 A CN201080030202 A CN 201080030202A CN 102471678 B CN102471678 B CN 102471678B
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- 239000001301 oxygen Substances 0.000 claims abstract description 38
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 35
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 7
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- 238000005401 electroluminescence Methods 0.000 claims description 8
- 229940125890 compound Ia Drugs 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract description 36
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
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- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
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- POXIZPBFFUKMEQ-UHFFFAOYSA-N 2-cyanoethenylideneazanide Chemical group [N-]=C=[C+]C#N POXIZPBFFUKMEQ-UHFFFAOYSA-N 0.000 description 1
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- 125000004429 atom Chemical group 0.000 description 1
- BNBQRQQYDMDJAH-UHFFFAOYSA-N benzodioxan Chemical compound C1=CC=C2OCCOC2=C1 BNBQRQQYDMDJAH-UHFFFAOYSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 229910000085 borane Inorganic materials 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
- RJCQBQGAPKAMLL-UHFFFAOYSA-N bromotrifluoromethane Chemical compound FC(F)(F)Br RJCQBQGAPKAMLL-UHFFFAOYSA-N 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- 235000011132 calcium sulphate Nutrition 0.000 description 1
- 239000001175 calcium sulphate Substances 0.000 description 1
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 125000005518 carboxamido group Chemical group 0.000 description 1
- 125000005111 carboxyalkoxy group Chemical group 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012069 chiral reagent Substances 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- OTAFHZMPRISVEM-UHFFFAOYSA-N chromone Chemical compound C1=CC=C2C(=O)C=COC2=C1 OTAFHZMPRISVEM-UHFFFAOYSA-N 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 125000004446 heteroarylalkyl group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 150000001261 hydroxy acids Chemical group 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- RHZWSUVWRRXEJF-UHFFFAOYSA-N indium tin Chemical compound [In].[Sn] RHZWSUVWRRXEJF-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 1
- RTRAMYYYHJZWQK-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1 RTRAMYYYHJZWQK-UHFFFAOYSA-N 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 230000004807 localization Effects 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 238000011326 mechanical measurement Methods 0.000 description 1
- 229910001512 metal fluoride Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000004373 methylthiopropyl group Chemical group [H]C([H])([H])SC([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- JGOAZQAXRONCCI-SDNWHVSQSA-N n-[(e)-benzylideneamino]aniline Chemical compound C=1C=CC=CC=1N\N=C\C1=CC=CC=C1 JGOAZQAXRONCCI-SDNWHVSQSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- WHLAXDUXKMECTM-UHFFFAOYSA-N oxadiazol-4-amine Chemical group NC1=CON=N1 WHLAXDUXKMECTM-UHFFFAOYSA-N 0.000 description 1
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 1
- 238000005240 physical vapour deposition Methods 0.000 description 1
- 229920000548 poly(silane) polymer Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229940093916 potassium phosphate Drugs 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- DLUARZOQVAUCSS-UHFFFAOYSA-N propan-2-ylperoxycyclopropane Chemical compound C(C)(C)OOC1CC1 DLUARZOQVAUCSS-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 238000003380 quartz crystal microbalance Methods 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052706 scandium Inorganic materials 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010129 solution processing Methods 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 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 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 239000006200 vaporizer Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/115—Polyfluorene; Derivatives thereof
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H10K71/40—Thermal treatment, e.g. annealing in the presence of a solvent vapour
Abstract
光电设备,包括式I的三线态阻挡化合物,其中,R1每次出现时独立是C1-20烃基且至少一个R1是R3;R2每次出现时独立是C1-20烃基、C1-20烃基氧基、C1-20硫醚、C1-20烃基羰基氧基或氰基;R3是-R4XR5;R4是直接键、C1-20芳基、C1-20芳基烷基、C1-20烷基芳基、C1-20取代的芳基、C1-20取代的芳基烷基或C1-20取代的烷基芳基;R5是C1-20烃基或含有至少一个在碳原子之间的S、N、O或P原子的C1-20烃基;R6是C1-20烷基或C1-20取代的烷基;X是-O-、-S-、-COO-、-OOC-、-CSS-、-SSC-、NR6或PR6;a每次出现时独立是0、1或2;和n是0或1。
Description
背景
在OLED设备中,分别从阴极和阳极注入的电子和空穴在发射层中结合,产生可辐射性衰减发光或非辐射性衰减产热的单线态和三线态激子。对于大多数有机分子,三线态的光发射是不与非辐射性衰减模式良好竞争的自旋禁阻过程,所以三线态激子不太具有发射性。由于自旋轨道耦合,所以过渡金属络合物可以与非辐射性途径竞争的效率辐射性衰减。当将这些络合物掺入OLED设备时,可能实现接近100%的内部量子效率,因为在设备中产生的单线态和三线态激子都可发光。
对于溶液可加工的OLED设备,典型地将过渡金属络合物通过共混或经过与聚合物主体共价连接而掺入聚合物主体内。适合这些类型设备的聚合物主体具有高于发射性客体过渡金属络合物的三线态能量以确保有利的能量转移。在主体聚合物中产生的三线态激子迁移直至它们遇到发射性客体,此时能量转移激发客体,出现光发射。来自主体的三线态激子还可向阳极或阴极迁移,其中可将它们以非辐射性方式猝灭。因此理想的是限制三线态激子以使遇到发射性客体的可能性最大和防止向电极特别是阴极迁移。防止激子向阴极迁移的一种方法是在阴极与发射层之间插入具有大于主体发射层的三线态能量的阻挡层。阻挡层还可促使从阴极注入电子和具有良好的电子移动性。简述
简言之,在一方面,本发明涉及光电设备,特别是OLED,它包括式I的三线态阻挡化合物
其中
R1每次出现时独立是C1-20烃基且
至少一个R1是R3;
R2每次出现时独立是C1-20烃基、C1-20烃基氧基、C1-20硫醚、C1-20烃基羰基氧基或氰基;
R3是-R4XR5;
R4是直接键、C1-20芳基、C1-20芳基烷基、C1-20烷基芳基、C1-20取代的芳基、C1-20取代的芳基烷基或C1-20取代的烷基芳基;
R5是C1-20烃基或者含有至少一个在碳原子之间的S、N、O或P原子的C1-20烃基;
R6是C1-20烷基或C1-20取代的烷基;
X是-O-、-S-、-COO-、-OOC-、-CSS-、-SSC-、NR6或PR6;
a每次出现时独立是0、1或2;和
n是0或1。
在另一方面,本发明涉及式Ia化合物
R1每次出现时独立是C1-20烃基且
至少一个R1是R3a;
R2每次出现时独立是C1-20烃基、C1-20烃基氧基、C1-20硫醚、C1-20烃基羰基氧基或氰基;
R3a是含有至少一个在碳原子之间的S、N、O或P原子的C1-20烃基;
a每次出现时独立是0、1或2;和
n是0或1。
详述
本发明涉及光电设备,它包括一系列层:阳极,典型地是氧化锡铟(ITO);促进正电荷载体从ITO注入有机层内的空穴注入层;将电子和空穴再结合以发光的一种或多种发射层;包括式I或Ia化合物的电子传输和三线态阻挡层;和电子注入阴极。
表1显示当低聚物中的芴单元总数改变时能量水平的排序。包含低聚物单元的聚合物还具有可比较的LUMO水平(由此促使电子注入发射层内)和稍微更深的HOMO水平,由此抑制空穴从发射层迁移。最终,这些材料具有使多层设备能够进行溶液加工制造的溶解度特性。
表1显示具有低聚物长度的三线态能量测量演变的参考7的谱数据.
芴单元数 | 三线态能量(eV) |
1 | 2.85 |
3 | 2.25 |
5 | 2.18 |
7 | 2.16 |
聚合物 | 2.11 |
由此,式I化合物非常适合用作其中发射层的三线态水平等于或低于聚芴的(T1=2.11eV)的设备中的三线态阻挡层。
为了满足这些材料提升电子注入和移动性的需要,本发明的光电设备包括在芴片段的9-位携带极性取代基的化合物。因此,在一方面,本发明涉及可在光电设备中用作三线态阻挡材料的式1化合物。极性取代基包括至少一个在碳原子之间的S、N、O或P原子,可包括至多约10个S、N、O或P杂原子。术语“在碳原子之间”指杂原子不是末端基团比如羟基、羰基、羧基、醛基(-CHO)的一部分;在碳原子之间的基团包括,但不限于醚、硫醚、酯、硫酯和氨基。杂原子可以全部都是一种类型,例如全部都是O原子,或者可以是S、N、O和P中一些或全部的混合物。特别是,杂原子可作为一种或多种醚、硫醚、酯、硫酯或氨基的一部分存在。
在特定实施方案中,式I化合物是下式化合物
在其它实施方案中,式I化合物是下式化合物
R1每次出现时独立可以是烷基或R3。
更具体来讲,在式1化合物中,R3可以是
其中
R7是C1-20烃基、C1-20烃基氧基、C1-20硫醚、C1-20烃基羰基氧基或氰基;和
b是0、1或2。
R5可以是吗啉基或吡咯烷基,特别是,R5可选自
在具体实施方案中,R3可以是-O(CH2CH2O)mCH2CH2NR6;m是0或0-约20的整数,或者R3可选自
在本发明的例示性化合物中,
--R1是C8H17且R3选自
--R1是且
R3选自
--R1是C8H17且R3是
--R1是C8H17且R3是
--R1是C8H17且R3是
--R1是C8H17且R3是
--R1是且R3是
--R1是且R3是
--R1是且R3是
--R1是且R3是
在另一方面,本发明涉及光电设备,其包含
阴极;
阳极;
位于阴极与阳极之间的电致发光层;和
位于电致发光层与阴极之间的层,包含式Ia化合物。
式Ia化合物涵盖的种类包括式I化合物。
在一些实施方案中,式Ia化合物是
在其它实施方案中,式Ia化合物是
在还有其它实施方案中,光电设备包括式1a化合物,其中R3a是含有至少一个醚、硫醚、酯、硫酯或烷基氨基的C1-20烃基。
合适的低聚物阻挡层的一些实例在表2提出。
表2.低聚芴三线态阻挡材料
式I化合物典型地是可通过用合适的有机溶剂蒸发流延(evaporative casting)流延成薄膜的非晶态材料。只要芴低聚物长度不超过约3个芴片段,这些低聚物的三线态能量高于大多数发射性主体材料,可出现三线态阻挡。
式I化合物可以很容易地通过典型的芳基偶联反应比如Suzuki或Yamamoto偶联制备。特别是,化合物可以通过Suzuki交叉偶联反应制备。Suzuki交叉偶联反应的一般程序包括使芳基卤与芳基硼酸酯(或亚硼酸(boronic acid))在合适溶剂中混合,在碱和Pd催化剂的存在下,在惰性气氛下加热。合适的溶剂包括,但不限于,二噁烷、THF、乙醇、甲苯及其混合物。例示性碱包括Na2CO3、K2CO3、Cs2CO3、磷酸钾及其水合物。可将碱作为固体粉剂或作为水溶液加入反应物内。合适的催化剂包括添加第二配体的Pd(PPh3)4、Pd(OAc)2和Pd(dba)2。例示性配体包括下文显示的二烷基膦基联苯基配体,其中Cy是环己基。
在最简单的情况下,光电设备包括阳极层和对应的阴极层以及位于阳极与阴极之间的电致发光层。当跨电极施加偏压时,电子从阴极注入电致发光层内,同时电子离开电致发光层(或“空穴”自阳极“注”入电致发光层)进入阳极。对于有机发光设备(OLED),发光出现在空穴与电子在电致发光层内结合以形成单线态或三线态激子时,当单线态和/或三线态激子经过辐射衰减衰减为其基态时出现发光。对于光伏(PV)设备,光吸收导致电流流动。
除了阳极、阴极和发光材料以外,可存在于光电设备中的其它组分包括空穴注入层、电子注入层和电子传输层。电子传输层不必直接接触阴极,电子传输层经常还充当空穴阻挡层以防止空穴向阴极迁移。可存在于有机发光设备中的其它组分包括空穴传输层、空穴传输发射(发射)层和电子传输发射(发射)层。
有机电致发光层,即发射层,是在有机发光设备内的层,当操作时它含有显著浓度的电子和空穴,提供激子形成和发光的位点。空穴注入层是与阳极接触的层,促使空穴从阳极注入OLED的内层;电子注入层是与阴极接触的层,促使电子从阴极注入OLED内;电子传输层是促进电子从阴极和/或电子注入层传导至电荷再结合位点的层。在包含电子传输层的有机发光设备操作过程中,存在于电子传输层中的大部分电荷载体(即空穴和电子)是电子,通过存在于发射层中空穴和电子的再结合可出现发光。空穴传输层是当OLED操作时促进空穴从阳极和/或空穴注入层传导至电荷再结合位点的层,不必直接接触阳极。空穴传输发射层是当OLED操作时促进空穴传导至电荷再结合位点的层,其中大部分电荷载体是空穴,其中发射不仅通过与残留电子再结合而出现,还通过从设备中其它地方电荷再结合区转移能量而出现。电子传输发射层是当OLED操作时促进电子传导至电荷再结合位点的层,其中大部分电荷载体是电子,其中发射不仅通过与残留空穴再结合而出现,还通过从设备中其它地方电荷再结合区转移能量而出现。
适合用作阳极的材料包括具有优选约1000ohm/平方的体电阻率的材料,如通过四点探针技术测量。氧化锡铟(ITO)经常用作阳极,因为它基本对光传输透明,由此促进从电活性有机层发的光逃逸。可用作阳极层的其它材料,包括氧化锡、氧化铟、氧化锌、氧化锌铟、氧化锡铟锌、氧化锑,及其混合物。
适合用作阴极的材料包括一般的电导体,包括但不限于可将负电荷载体(电子)注入OLED内层的金属。还可使用金属氧化物比如ITO。适合用作阴极的金属包括K、Li、Na、Cs、Mg、Ca、Sr、Ba、Al、Ag、Au、In、Sn、Zn、Zr、Sc、Y、镧系元素、其合金,及其混合物。用作阴极层的合适的合金材料包括Ag-Mg、Al-Li、In-Mg、Al-Ca和Al-Au合金。分层非合金结构也可用于阴极,比如薄层的金属比如钙,或者金属氟化物,比如LiF,其由较厚层的金属比如铝或银覆盖。特别是,阴极可由单种金属、尤其是铝金属组成。
式I化合物可代替或者补充传统材料而用于电子传输层中,比如聚(9,9-二辛基芴)、三(8-羟基喹啉)铝(Alq3)、2,9-二甲基-4,7-二苯基-1,1-菲咯啉、4,7-二苯基-1,10-菲咯啉、2-(4-联苯基)-5-(4-叔丁基苯基)-1,3,4-噁二唑、3-(4-联苯基)-4-苯基-5-(4-叔丁基苯基)-1,2,4-三唑、含1,3,4-噁二唑聚合物、含1,3,4-三唑聚合物、含喹噁啉聚合物,和氰基-PPV。
适合用于空穴传输层的材料包括1,1-双((二-4-甲苯基氨基)苯基)环己烷、N,N′-双(4-甲基苯基)-N,N′-双(4-乙基苯基)-(1,1′-(3,3′-二甲基)联苯基)-4,4′-二胺、四-(3-甲基苯基)-N,N,N′,N′-2,5-苯二胺、苯基-4-N,N-二苯基氨基苯乙烯、对-(二乙基氨基)苯甲醛二苯基腙、三苯基胺、1-苯基-3-(对-(二乙基氨基)苯乙烯基)-5-(对-(二乙基氨基)苯基)吡唑啉、1,2-反式-双(9H-咔唑-9-基)环丁烷、N,N,N′,N′-四(4-甲基苯基)-(1,1′-联苯基)-4,4′-二胺、铜酞菁、聚乙烯基咔唑、(苯基甲基)聚硅烷;聚(3,4-乙二氧基噻吩)(PEDOT)、聚苯胺、聚乙烯基咔唑、三芳基二胺、四苯基二胺、芳族叔胺、腙衍生物、咔唑衍生物、三唑衍生物、咪唑衍生物、具有氨基的噁二唑衍生物,和聚噻吩,如公开于美国专利号6,023,371。
适合用于发光层的材料包括电致发光聚合物比如聚芴,优选聚(9,9-二辛基芴)及其共聚物,比如聚(9,9′-二辛基芴-共-双-N,N′-(4-丁基苯基)二苯基胺)(F8-TFB);聚(乙烯基咔唑)和聚亚苯基亚乙烯及其衍生物。此外,发光层可包括蓝色、黄色、橙色、绿色或红色磷光性染料或金属络合物,或其组合。适合用作磷光性染料的材料包括,但不限于,三(1-苯基异喹啉)铱(III)(红色染料)、三(2-苯基吡啶)铱(绿色染料)和铱(III)双(2-(4,6-二氟苯基)吡啶-N,C2)(蓝色染料)。还可使用市售获得自ADS(American Dyes Source,Inc.)的电致荧光和电致磷光金属络合物。ADS绿色染料包括ADS060GE、ADS061GE、ADS063GE和ADS066GE、ADS078GE和ADS090GE。ADS蓝色染料包括ADS064BE、ADS065BE和ADS070BE。ADS红色染料包括ADS067RE、ADS068RE、ADS069RE、ADS075RE、ADS076RE、ADS067RE和ADS077RE。
定义
术语烃基用于本文,除非另外指明,指只含有氢和碳的任何有机部分,可包括芳族、脂族、环脂族和含有两个或多个脂族、环脂族或芳族部分的部分。
如用于本文,烷基意图包括线性、分枝或环状烃结构及其组合,包括低级烷基和高级烷基。优选烷基是C20或以下的烷基。低级烷基指1-6个碳原子、优选1-4个碳原子的烷基,包括甲基、乙基、正丙基、异丙基,和正-、仲-和叔-丁基。高级烷基指具有7个或更多碳原子、优选7-20个碳原子的烷基,包括正-、仲-和叔-庚基、辛基和十二烷基。环烷基是烷基的亚组,包括3-8个碳原子的环状烃基。环烷基的实例包括环丙基、环丁基、环戊基和降冰片基。烯基和炔基分别指其中两个或更多氢原子被双键或三键代替的烷基。
芳基和杂芳基指含有0-3个选自氮、氧或硫的杂原子的5-或6-元芳环或杂芳环;含有0-3个选自氮、氧或硫的杂原子的双环9-或10-元芳环或杂芳环系统;或者含有0-3个选自氮、氧或硫的杂原子的三环13-或14-元芳环或杂芳环系统。芳族6-至14-元碳环包括例如苯、萘、茚满、四氢萘和芴;5-至10-元芳族杂环包括例如咪唑、吡啶、吲哚、噻吩、苯并吡喃酮、噻唑、呋喃、苯并咪唑、喹啉、异喹啉、喹噁啉、嘧啶、吡嗪、四唑和吡唑。
芳基烷基指与芳环连接的烷基残基。实例是苯甲基和苯乙基。杂芳基烷基指与杂芳环连接的烷基残基。实例包括吡啶基甲基和嘧啶基乙基。烷基芳基指具有一个或多个烷基连接其上的芳基残基。实例是甲苯基和均三甲苯基。
烷氧基(Alkoxy)或烷氧基(alkoxyl)指通过氧与母结构连接的1-8个碳原子的直线、分枝、环状构型及其组合的基团。实例包括甲氧基、乙氧基、丙氧基、异丙氧基、环丙基氧基和环己基氧基。低级烷氧基指含有1-4个碳的基团。
酰基指通过羰基官能团与母结构连接的1-8个碳原子的直线、分枝、环状构型,其为饱和、不饱和和芳族及其组合。在酰基残基中的一个或多个碳可被氮、氧或硫代替,只要与母体的连接点保持在羰基处。实例包括乙酰基、苯甲酰基、丙酰基、异丁酰基、叔丁氧基羰基和苯甲氧基羰基。低级酰基指含有1-4个碳的基团。
杂环指其中1-2个碳被杂原子比如氧、氮或硫代替的环烷基或芳基残基。落在本发明范围内的杂环实例包括吡咯烷、吡唑、吡咯、吲哚、喹啉、异喹啉、四氢异喹啉、苯并呋喃、苯并二噁烷、苯并二噁茂(当作为取代基出现时通常称为亚甲基二氧基苯基)、四唑、吗啉、噻唑、吡啶、哒嗪、嘧啶、噻吩、呋喃、噁唑、噁唑啉、异噁唑、二噁烷和四氢呋喃。
取代的指残基,包括但不限于烷基、烷基芳基、芳基、芳基烷基和杂芳基,其中残基的至多3个H原子被低级烷基、取代的烷基、烯基、取代的烯基、芳基、取代的芳基、卤代烷基、烷氧基、羰基、羧基、羧基烷氧基(carboxalkoxy)、羧酰氨基、酰氧基、脒基、硝基、卤代基、羟基、OCH(COOH)2、氰基、伯氨基、仲氨基、酰基氨基、烷基硫代基、亚砜、砜、苯基、苯甲基、苯氧基、苯甲氧基、杂芳基或杂芳基氧基代替。
卤代烷基指烷基残基,其中一个或多个H原子被卤素原子代替;术语卤代烷基包括全卤代烷基。落在本发明范围内的卤代烷基实例包括CH2F、CHF2和CF3。
许多本文所述化合物可含有一个或多个不对称中心,由此可产生对映体、非对映体及其它立体异构形式,可根据绝对立体化学限定为(R)-或(S)-。本发明意欲包括所有此类可能的异构体,及其外消旋和旋光纯形式。旋光活性(R)-和(S)-异构体可用手性合成子或手性试剂制备,或者用常规技术拆分。当本文所述化合物含有烯属双键或其它几何不对称中心时,除非另外指定,该化合物意图包括E和Z几何异构体二者。同样,还意图包括所有互变异构形式。
氧杂烷基指其中一个或多个碳已被氧代替的烷基残基。它通过烷基残基与母结构连接。实例包括甲氧基丙氧基、3,6,9-三氧杂癸基等。术语氧杂烷基意图如在本领域所理解的[见Naming and Indexing of Chemical Substances for Chemical Abstracts(化学文摘用化学物质命名 及索引),American Chemical Society出版,但不受的限制],即指其中氧经单键与其相邻原子键合(形成醚键)的化合物;不是指双键键合的氧,如在羰基中所见。类似地,硫杂烷基和氮杂烷基分别指其中一个或多个碳已被硫或氮代替的烷基残基。实例包括乙基氨基乙基和甲基硫代丙基。
甲硅烷基指其中1-3个碳被四价硅代替且通过硅原子与母结构连接的烷基残基。甲硅烷氧基是烷氧基残基,其中两个碳都被用烷基残基、芳基残基或环烷基残基封端的四价硅代替,且通过氧原子与母结构连接。
如用于本文,术语“芳族原子团(radical)”指包含至少一个芳族基团的化合价至少为1的原子排列。包含至少一个芳族基团的化合价至少为1的原子排列可包括杂原子比如氮、硫、硒、硅和氧,或者可排他地由碳和氢组成。如用于本文,术语“芳族原子团”包括但不限于苯基、吡啶基、呋喃基、噻吩基、萘基、亚苯基和联苯基原子团。如上文提到,芳族原子团含有至少一个芳族基团。芳族基团一定是具有4n+2个“不定域”电子的环状结构,其中“n”是等于1或更大的整数,例如苯基(n=1)、噻吩基(n=1)、呋喃基(n=1)、萘基(n=2)、薁基(n=2)、蒽基(n=3)等。芳族原子团还可包括非芳族组分。例如,苯甲基是包含苯环(芳族基团)和亚甲基(非芳族组分)的芳族原子团。类似地四氢萘基原子团是包含与非芳族组分-(CH2)4-稠合的芳族基团(C6H3)的芳族原子团。为了方便,术语“芳族原子团”在本文限定为涵盖广泛范围的官能团比如烷基、烯基、炔基、卤代烷基、卤代芳族基团、共轭二烯基、醇基、醚基、醛基、酮基、羧酸基团、酰基(例如羧酸衍生物比如酯和酰胺)、胺基、硝基等。例如,4-甲基苯基原子团是包含甲基的C7芳族原子团,甲基是烷基官能团。类似地,2-硝基苯基是包含硝基的C6芳族原子团,硝基是官能团。芳族原子团包括卤代芳族原子团比如4-三氟甲基苯基、六氟异亚丙基双(4-苯-1-基氧基)(即-OPhC(CF3)2PhO-)、4-氯甲基苯-1-基、3-三氟乙烯基-2-噻吩基、3-三氯甲基苯-1-基(即3-CCl3Ph-)、4-(3-溴丙-1-基)苯-1-基(即4-BrCH2CH2CH2Ph-)等。芳族原子团的其它实例包括4-烯丙基氧基苯-1-氧基、4-氨基苯-1-基(即4-H2NPh-)、3-氨基羰基苯-1-基(即NH2COPh-)、4-苯甲酰基苯-1-基、二氰基亚甲基双(4-苯-1-基氧基)(即-OPhC(CN)2PhO-)、3-甲基苯-1-基、亚甲基双(4-苯-1-基氧基)(即-OPhCH2PhO-)、2-乙基苯-1-基、苯基乙烯基、3-甲酰基-2-噻吩基、2-己基-5-呋喃基、六亚甲基-1,6-双(4-苯-1-基氧基)(即-OPh(CH2)6PhO-)、4-羟基甲基苯-1-基(即4-HOCH2Ph-)、4-巯基甲基苯-1-基(即4-HSCH2Ph-)、4-甲基噻吩-1-基(即4-CH3SPh-)、3-甲氧基苯-1-基、2-甲氧基羰基苯-1-基氧基(如甲基水杨酰基)、2-硝基甲基苯-1-基(即2-NO2CH2Ph)、3-三甲基甲硅烷基苯-1-基、4-叔丁基二甲基甲硅烷基苯-1-基、4-乙烯基苯-1-基、亚乙烯基双(苯基)等。术语“C3-C10芳族原子团”包括含有至少3个但不超过10个碳原子的芳族原子团。芳族原子团1-咪唑基(C3H2N2-)代表C3芳族原子团。苯甲基原子团(C7H7-)代表C7芳族原子团。
如用于本文术语“环脂族原子团”指化合价至少为1,且包含环状但不是芳族的原子排列的原子团。如本文限定“环脂族原子团”不含有芳族基团。“环脂族原子团”可包含一个或多个非环状组分。例如,环己基甲基(C6H11CH2-)是包含环己基环(环状但非芳族的原子排列)和亚甲基(非环状组分)的环脂族原子团。环脂族原子团可包括杂原子比如氮、硫、硒、硅和氧,或者可排他地由碳和氢组成。为了方便,术语“环脂族原子团”在本文限定为涵盖广泛范围的官能团比如烷基、烯基、炔基、卤代烷基、共轭二烯基、醇基、醚基、醛基、酮基、羧酸基、酰基(例如羧酸衍生物比如酯和酰胺)、胺基、硝基等。例如,4-甲基环戊-1-基原子团是包含甲基的C6环脂族原子团,甲基是烷基官能团。类似地,2-硝基环丁-1-基是包含硝基的C4环脂族原子团,硝基是官能团。环脂族原子团可包含一个或多个卤素原子,它们可相同或不同。卤素原子包括例如:氟、氯、溴和碘。包含一个或多个卤素原子的环脂族原子团包括2-三氟甲基环己-1-基、4-溴二氟甲基环辛-1-基、2-氯二氟甲基环己-1-基、六氟异亚丙基-2,2-双(环己-4-基)(即-C6H10C(CF3)2C6H10-)、2-氯甲基环己-1-基、3-二氟亚甲基环己-1-基、4-三氯甲基环己-1-基氧基、4-溴二氯甲基环己-1-基硫基、2-溴乙基环戊-1-基、2-溴丙基环己-1-基氧基(如CH3CHBrCH2C6H10O-)等。环脂族原子团的其它实例包括4-烯丙基氧基环己-1-基、4-氨基环己-1-基(即H2NC6H10-)、4-氨基羰基环戊-1-基(即NH2COC5H8-)、4-乙酰基氧基环己-1-基、2,2-二氰基异亚丙基双(环-己-4-基氧基)(即-OC6H10C(CN)2C6H10O-)、3-甲基环己-1-基、亚甲基双(环己-4-基氧基)(即-OC6H10CH2C6H10O-)、1-乙基环丁-1-基、环丙基乙烯基、3-甲酰基-2-四氢呋喃基、2-己基-5-四氢呋喃基、六亚甲基-1,6-双(环己-4-基氧基)(即-OC6H10(CH2)6C6H10O-)、4-羟基甲基环己-1-基(即4-HOCH2C6H10-)、4-巯基甲基环己-1-基(即4-HSCH2C6H10-)、4-甲基硫基环己-1-基(即4-CH3SC6H10-)、4-甲氧基环己-1-基、2-甲氧基羰基环己-1-基氧基(2-CH3OCOC6H10O-)、4-硝基甲基环己-1-基(即NO2CH2C6H10-)、3-三甲基甲硅烷基环己-1-基、2-叔丁基二甲基甲硅烷基环戊-1-基、4-三甲氧基甲硅烷基乙基环己-1-基(如(CH3O)3SiCH2CH2C6H10-)、4-乙烯基环己烯-1-基、亚乙烯基双(环己基)等。术语“C3-C10环脂族原子团”包括含有至少3个但不超过10个碳原子的环脂族原子团。环脂族原子团2-四氢呋喃基(C4H7O-)代表C4环脂族原子团。环己基甲基原子团(C6H11CH2-)代表C7环脂族原子团。
如用于本文术语“脂族原子团”指由线性或支链且非环状的原子排列组成的化合价至少为1的有机原子团。限定脂族原子团包含至少一个碳原子。包含脂族原子团的原子排列可包括杂原子比如氮、硫、硅、硒和氧或者可排他地由除碳和氢组成。为了方便,术语“脂族原子团”在本文限定为涵盖作为被广泛范围的官能团取代的“直线或分枝非环状原子排列”的一部分,所述官能团比如烷基、烯基、炔基、卤代烷基、共轭二烯基、醇基、醚基、醛基、酮基、羧酸基、酰基(例如羧酸衍生物比如酯和酰胺)、胺基、硝基等。例如,4-甲基戊-1-基原子团是包含甲基的C6脂族原子团,甲基是烷基官能团。类似地,4-硝基丁-1-基是包含硝基的C4脂族原子团,硝基是官能团。脂族原子团可以是包含一个或多个可以相同或不同的卤素原子的卤代烷基。卤素原子包括例如:氟、氯、溴和碘。包含一个或多个卤素原子的脂族原子团包括烷基卤:三氟甲基、溴二氟甲基、氯二氟甲基、六氟异亚丙基、氯甲基、二氟亚乙烯基、三氯甲基、溴二氯甲基、溴乙基、2-溴三亚甲基(如-CH2CHBrCH2-)等。其它脂族原子团实例包括烯丙基、氨基羰基(即-CONH2)、羰基、2,2-二氰基异亚丙基(即-CH2C(CN)2CH2-)、甲基(即-CH3)、亚甲基(即-CH2-)、乙基、乙烯、甲酰基(即-CHO)、己基、六亚甲基、羟基甲基(即-CH2OH)、巯基甲基(即-CH2SH)、甲基硫基(即-SCH3)、甲基硫基甲基(即-CH2SCH3)、甲氧基、甲氧基羰基(即CH3OCO-)、硝基甲基(即-CH2NO2)、硫基羰基、三甲基甲硅烷基(即(CH3)3Si-)、叔丁基二甲基甲硅烷基、3-三甲基氧基甲硅烷基丙基(即(CH3O)3SiCH2CH2CH2-)、乙烯基、亚乙烯基等。通过进一步举例,C1-C10脂族原子团含有至少1个但不超过10个碳原子。甲基(即CH3-)是C1脂族原子团的实例。癸基(即CH3(CH2)9-)是C10脂族原子团的实例。
实施例
实施例1低聚芴的制备
制备低聚芴的一般程序用392-59的合成举例:向配备冷凝器、气体进入管和特氟隆(Teflon)磁力搅拌棒的200ml 2-颈烧瓶内装入9,9-双-(4-己基氧基苯基)-2,7-二溴芴2.028g(3.00mmol)、9,9-二辛基-2-亚乙基二氧基硼烷3.132g(6.24mmol)、二环己基-2-(2’,6’-二-甲氧基苯基)苯基膦0.129g(0.32mmol)和甲苯60ml。将溶液用氩气脱气15分钟,加入乙酸钯0.20g(0.09mmol),接着加入四乙基氢氧化铵2.2g(15mmol)在水22g中的脱气溶液。将溶液浸在70℃油浴中,在氮气层下搅拌16小时。将冷却的混合物用甲苯50ml和水25ml稀释,用硅藻土(Celite)垫过滤,转移至分液漏斗中。弃去水相,将有机相连续用水(2×100ml)和盐水(1×100ml)洗涤,然后穿过无水硫酸钙(Drierite)锥形漏斗。将溶液在室温下用硼氢化钠~25mg搅拌,然后真空浓缩,将残留油状物在120g硅胶上层析,用0-30%乙酸乙酯的己烷溶液洗脱以得到2.3g无色油状物:1H nmr(CDCl3)δ8.0-7.3(m,20,芴-H),7.3-6.8(AB四重峰,8,酚醚Ar-H),3.96(t,4,ArOCH2),2.04(t,8,C9-CH2),和1.8-0.6ppm(m,60,辛基-H)。
实施例2多层结构
本发明的材料可溶于普通的醇比如1-丁醇和1己醇。例如,我们已发现材料比如JC392-59和392-38可以很容易以接近10mg/ml浓度溶解于1-己醇和1-丁醇。一旦冷却至室温,这种材料可以经过旋转流延直接从溶液沉积在不被醇溶剂溶解的聚-芴聚合物层上。我们已发现将~10mg/ml醇溶液以~1000rpm旋转涂布在聚芴涂布的玻片上导致厚~20nm的附加膜,我们将其指定为三聚体类型材料的附加层。我们已发现在形成这种双层结构之后可以对玻璃上聚合物膜进行机械和光学厚度测量。进行机械测量,首先用锐利的边缘刮擦膜,接着用轮廓曲线仪(在这种情况下是Tencor P1)测量膜顶端与玻璃之间的距离。利用聚芴材料在其光吸收中~390nm处显示峰且在~357nm吸收小很多,而许多本发明的三聚体类别的峰吸收在~357nm处吸收的事实,进行光学测量。由此可以将由层合并的吸收解卷积为两种组分,一种对应于聚-芴,另一种对应于本发明的低聚物。因为光吸收(以OD单位)与平均厚度线性相关,这为双层结构的存在提供了附加支持。
实施例3:掺入多层结构的OLED
可以用这些材料有利的溶解度特性制造OLED设备。为了制造设备,可通过旋转涂布在干净、UV-臭氧处理的2.5cm×2.5cm ITO图案化玻璃基板上,获得厚度约60nm的PEDOT/PSS(Baytron P VP 8000,作为溶液获得自HC Starck,Inc.的聚(3,4-亚乙基二氧基噻吩)-聚(苯乙烯磺酸酯))或其它空穴注入材料层。然后可将涂布的基板在空气中在160℃热板上烘烤30分钟。可将一层厚度约10-20nm的F8-TFB(从Sumation,Inc.获得的辛基芴-三芳基胺共聚物)空穴传输层经过旋转涂布沉积在PEDOT/PSS涂布基板顶端。然后可将F8-TFB-PEDOT/PSS涂布基板在氩气中在160℃热板上烘烤30分钟。然后可使一层包含非醇溶性聚芴材料(从Sumation chemical或American Dye Source获得)溶于溶剂比如二甲苯中,并沉积在F8-TFB层顶端作为发射层。虽然这种发射层的厚度可变化至最多为200nm,但优选5nm-40nm厚度。可使最后一层三聚体材料层从醇(例如1-丁醇、1-己醇)溶液中沉积,优选厚度为10nm-50nm。
然后可将涂布基板放入钟罩蒸发器内,抽吸系统直至获得约1×10-6托压力。然后可将约7nm厚(如经过校准的石英晶体微量天平测量)的氟化钠层通过物理蒸发沉积沉积在涂布基板最后一层顶端。随后,可将约130nm厚的铝金属层通过真空蒸发沉积沉积在氟化钠层顶端以形成OLED的阴极组分。
虽然本文已说明和描述的只是本发明的某些特征,但本领域技术人员将想到许多修饰和改变。因此,应理解所附权利要求旨在覆盖所有此类修饰和改变,认为落在本发明真正的精神内。
Claims (1)
1.一种光电设备,其包含
阴极;
阳极;
位于阴极与阳极之间的电致发光层;和
位于电致发光层与阴极之间的三线态阻挡层,该层包含式Ia化合物
Ia
R1每次出现时独立是C8H17且
至少一个R1是R3a;
R2每次出现时独立是C1-20烃基、C1-20烃基氧基、C1-20硫醚、C1-20烃基羰基氧基或氰基;
R3a选自
和
;
a每次出现时独立是0、1或2;和
n是0或1。
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-
2009
- 2009-06-29 US US12/493,781 patent/US20100327735A1/en not_active Abandoned
-
2010
- 2010-03-01 WO PCT/US2010/025718 patent/WO2011002532A1/en active Application Filing
- 2010-03-01 CN CN201080030202.0A patent/CN102471678B/zh not_active Expired - Fee Related
- 2010-03-01 KR KR1020127002428A patent/KR101537437B1/ko not_active IP Right Cessation
- 2010-03-01 JP JP2012517511A patent/JP2012532101A/ja not_active Withdrawn
- 2010-03-01 EP EP10707404A patent/EP2449053A1/en not_active Withdrawn
- 2010-06-15 TW TW099119505A patent/TWI507377B/zh not_active IP Right Cessation
-
2013
- 2013-05-20 US US13/897,653 patent/US20130248840A1/en not_active Abandoned
Also Published As
Publication number | Publication date |
---|---|
WO2011002532A1 (en) | 2011-01-06 |
EP2449053A1 (en) | 2012-05-09 |
TW201127780A (en) | 2011-08-16 |
TWI507377B (zh) | 2015-11-11 |
US20130248840A1 (en) | 2013-09-26 |
CN102471678A (zh) | 2012-05-23 |
JP2012532101A (ja) | 2012-12-13 |
KR101537437B1 (ko) | 2015-07-16 |
US20100327735A1 (en) | 2010-12-30 |
KR20120039676A (ko) | 2012-04-25 |
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