CN114369068A - 醌类有机化合物、混合物、组合物及有机电子器件 - Google Patents
醌类有机化合物、混合物、组合物及有机电子器件 Download PDFInfo
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- CN114369068A CN114369068A CN202011100726.4A CN202011100726A CN114369068A CN 114369068 A CN114369068 A CN 114369068A CN 202011100726 A CN202011100726 A CN 202011100726A CN 114369068 A CN114369068 A CN 114369068A
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- -1 Quinone organic compounds Chemical class 0.000 title claims abstract description 128
- AZQWKYJCGOJGHM-UHFFFAOYSA-N para-benzoquinone Natural products O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 title claims abstract description 48
- 239000000203 mixture Substances 0.000 title claims abstract description 46
- 239000000463 material Substances 0.000 claims abstract description 51
- 125000004432 carbon atom Chemical group C* 0.000 claims description 69
- 125000006413 ring segment Chemical group 0.000 claims description 46
- 125000003118 aryl group Chemical group 0.000 claims description 43
- 125000001072 heteroaryl group Chemical group 0.000 claims description 31
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 26
- 229910052794 bromium Inorganic materials 0.000 claims description 24
- 229910052731 fluorine Inorganic materials 0.000 claims description 24
- 229910052740 iodine Inorganic materials 0.000 claims description 24
- 125000000018 nitroso group Chemical group N(=O)* 0.000 claims description 24
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 229910052801 chlorine Inorganic materials 0.000 claims description 16
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 230000000903 blocking effect Effects 0.000 claims description 14
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 14
- 125000004122 cyclic group Chemical group 0.000 claims description 14
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000003960 organic solvent Substances 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 8
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
- AFYPFACVUDMOHA-UHFFFAOYSA-N chlorotrifluoromethane Chemical compound FC(F)(F)Cl AFYPFACVUDMOHA-UHFFFAOYSA-N 0.000 claims description 8
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 8
- 125000005067 haloformyl group Chemical group 0.000 claims description 8
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 8
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M thiocyanate group Chemical group [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000004104 aryloxy group Chemical group 0.000 claims description 7
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 7
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 7
- 125000002462 isocyano group Chemical group *[N+]#[C-] 0.000 claims description 7
- ZBKFYXZXZJPWNQ-UHFFFAOYSA-N isothiocyanate group Chemical group [N-]=C=S ZBKFYXZXZJPWNQ-UHFFFAOYSA-N 0.000 claims description 7
- 125000000468 ketone group Chemical group 0.000 claims description 7
- 230000004927 fusion Effects 0.000 claims description 5
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 22
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- 239000000758 substrate Substances 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 11
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
- 239000007795 chemical reaction product Substances 0.000 description 11
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 11
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
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- 125000001424 substituent group Chemical group 0.000 description 8
- 150000003254 radicals Chemical class 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
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- 125000004429 atom Chemical group 0.000 description 5
- GNKZMNRKLCTJAY-UHFFFAOYSA-N 4'-Methylacetophenone Chemical compound CC(=O)C1=CC=C(C)C=C1 GNKZMNRKLCTJAY-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
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- 125000000623 heterocyclic group Chemical group 0.000 description 4
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 4
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000003775 Density Functional Theory Methods 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 3
- 239000010405 anode material Substances 0.000 description 3
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000010406 cathode material Substances 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
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- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
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- NNWHUJCUHAELCL-SNAWJCMRSA-N trans-isomethyleugenol Chemical compound COC1=CC=C(\C=C\C)C=C1OC NNWHUJCUHAELCL-SNAWJCMRSA-N 0.000 description 3
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- 239000000314 lubricant Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
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- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- DYFFAVRFJWYYQO-UHFFFAOYSA-N n-methyl-n-phenylaniline Chemical compound C=1C=CC=CC=1N(C)C1=CC=CC=C1 DYFFAVRFJWYYQO-UHFFFAOYSA-N 0.000 description 1
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- 229940078552 o-xylene Drugs 0.000 description 1
- KSCKTBJJRVPGKM-UHFFFAOYSA-N octan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCCCCCC[O-].CCCCCCCC[O-].CCCCCCCC[O-].CCCCCCCC[O-] KSCKTBJJRVPGKM-UHFFFAOYSA-N 0.000 description 1
- 238000007645 offset printing Methods 0.000 description 1
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- 229920000642 polymer Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 1
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- 150000003230 pyrimidines Chemical class 0.000 description 1
- MHOZZUICEDXVGD-UHFFFAOYSA-N pyrrolo[2,3-d]imidazole Chemical class C1=NC2=CC=NC2=N1 MHOZZUICEDXVGD-UHFFFAOYSA-N 0.000 description 1
- RQGPLDBZHMVWCH-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole Chemical class C1=NC2=CC=NC2=C1 RQGPLDBZHMVWCH-UHFFFAOYSA-N 0.000 description 1
- 150000003246 quinazolines Chemical class 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 150000003252 quinoxalines Chemical class 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
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- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- 238000007764 slot die coating Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring 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
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- RUVINXPYWBROJD-ONEGZZNKSA-N trans-anethole Chemical compound COC1=CC=C(\C=C\C)C=C1 RUVINXPYWBROJD-ONEGZZNKSA-N 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07C25/24—Halogenated aromatic hydrocarbons with unsaturated side chains
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- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/50—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
- C07C255/51—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings containing at least two cyano groups bound to the carbon skeleton
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- C07C255/52—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of six-membered aromatic rings being part of condensed ring systems
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/90—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having more than three double bonds between ring members or between ring members and non-ring members
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- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
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- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/42—Benzopyrazines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
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- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/056—Ortho-condensed systems with two or more oxygen atoms as ring hetero atoms in the oxygen-containing ring
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Abstract
本发明公开了一种醌类有机化合物、混合物、组合物及其有机电子器件。该醌类有机化合物的结构如通式(I)所示,其可作为掺杂材料用于电子器件的功能层中,提高器件的效率和寿命。
Description
技术领域
本发明涉及有机致电发光领域,具体涉及一种醌类有机化合物、混合物、组合物及有机电子器件。
背景技术
在平板显示和照明应用中,有机发光二极管(OLEDs)具有低成本、轻重量、低工作电压、高亮度、颜色可调性、宽视角、易装配以及低能量消耗的优势,因而成为最有发展潜力的显示技术。为了提高有机发光二极管的发光效率,各种基于荧光和磷光发光材料体系已被开发出来。为了提高注入的空穴和电子的复合效率,需要进一步对有机发光二极管的结构和材料等方面进行改良。
目前默克公司利用芳香族二胺衍生物或芳香族稠环二胺衍生物作为有机发光二极管的空穴传输材料,以此来提高注入空穴的效率,但需要提高使用电压才可以使有机发光二极管充分发光,这就导致了有机发光二极管寿命降低和消耗电量增大的问题。
传统降低使用电压的方法是在有机发光二极管的空穴传输层中掺杂电子受体,例如四氰基醌二甲烷(TCNQ)、2,3,5,6-四氟-四氰基-1,4-苯并醌二甲烷(F4TCNQ)。然而,这些化合物在用于掺杂有机层时存在诸多缺陷,例如:在有机发光二极管的制作工序中操作不稳定,在有机发光二极管驱动时稳定性不足,寿命下降,或在用真空蒸镀来制造有机发光二极管时,上述化合物会在装置内扩散,污染装置。
因此人们希望进一步改进空穴传输层中掺杂的电子受体,以实现有机发光二极管低电压化和长寿命化。
发明内容
基于此,有必要提供一种醌类有机化合物,可作为掺杂材料用于电子器件的功能层中,提高器件的效率和寿命。
本发明通过如下技术方案实现。
一种醌类有机化合物,其结构如通式(I)所示:
其中:
X每次出现,分别独立地选自CR3或N;
M每次出现,分别独立地选自CR4Ar1;
Ar1每次出现,独立地选自被一个或多个R取代的具有5-60个环原子的芳香基团或杂芳香基团;所述R独立地选自D、硝基、亚硝基、CF3、Cl、Br、F、I或氰基;
R1、R2、R3、R4每次出现,分别独立选自H、D、具有1-20个碳原子的直链烷基、具有1-20个碳原子的直链烷氧基或硫代烷氧基、具有3-20个碳原子的支链或环状的烷基、具有3-20个碳原子的支链或环状的烷氧基、具有3-20个碳原子的支链或环状的硫代烷氧基、甲硅烷基、具有1-20个碳原子的酮基、具有2-20个碳原子的烷氧基羰基、具有7-20个碳原子的芳氧基羰基、氰基、氨基甲酰基、卤甲酰基、甲酰基、异氰基、异氰酸酯基、硫氰酸酯基、异硫氰酸酯基、羟基、硝基、亚硝基、烯基、CF3、C2F5、Cl、Br、F、I、可交联的基团、取代或未取代的具有5-60个环原子的芳香基团或杂芳香基团、具有5-60个环原子的芳氧基或杂芳氧基基团,或这些基团的组合;R1、R2互相成环或不成环。
本发明还提供一种混合物,该混合物包含如上所述的醌类有机化合物中的至少一种,及至少一种有机功能材料,所述的有机功能材料可选自空穴注入材料、空穴传输材料、电子传输材料、电子注入材料、电子阻挡材料、空穴阻挡材料、发光层、主体材料或有机染料。
本发明还提供一种组合物,该组合物包含如上所述的醌类有机化合物、混合物中的至少一种,及至少一种有机溶剂。
本发明还提供一种有机电子器件,该有机电子器件包含如上所述的醌类有机化合物、混合物中的至少一种或由上述的组合物制备而成。
与现有技术相比较,具有如下有益效果:
本发明的醌类有机化合物,具有优异的空穴传输性质及稳定性,可作为有机电致发光元件中的空穴注入层材料,也可以作为掺杂剂掺杂在空穴注入层或空穴传输层中,这样既可用低电压驱动,也可提高电致发光效率,延长器件寿命。
具体实施方式
以下结合具体实施例对本发明的醌类有机化合物、混合物、组合物及有机电子器件作进一步详细的说明。本发明可以以许多不同的形式来实现,并不限于本文所描述的实施方式。相反地,提供这些实施方式的目的是使对本发明公开内容理解更加透彻全面。
除非另有定义,本文所使用的所有的技术和科学术语与属于本发明的技术领域的技术人员通常理解的含义相同。本文中在本发明的说明书中所使用的术语只是为了描述具体的实施例的目的,不是旨在于限制本发明。
在本发明中,组合物和印刷油墨或油墨具有相同的含义,它们之间可以互换。
在本发明中,“取代”表示被取代基中的氢原子被取代基所取代。
在本发明中,同一取代基多次出现时,可独立选自不同基团。如通式含有多个R1,则R1可独立选自不同基团。
本发明中,“取代或未取代”表示所定义的基团可以被取代,也可以不被取代。当所定义的基团被取代时,应理解为任选被本领域可接受的基团所取代,包括但不限于:C1-30烷基、含有3-20个环原子的杂环基、含有5-20个环原子的芳基、含有5-20个环原子的杂芳基、硅烷基、羰基、烷氧基羰基、芳氧基羰基、氨基甲酰基、卤甲酰基、甲酰基、-NRR′、氰基、异氰基、异氰酸酯基、硫氰酸酯基、异硫氰酸酯基、羟基、三氟甲基、硝基或卤素,且上述基团也可以进一步被本领域可接受取代基取代;可理解的,-NRR′中的R和R′各自独立地为本领域可接受的基团所取代,包括但不限于H、C1-6烷基、含有3-8个环原子的环烷基、含有3-8个环原子的杂环基、含有5-20个环原子的芳基或含有5-10个环原子的杂芳基;所述C1-6烷基、含有3-8个环原子的环烷基、含有3-8个环原子的杂环基、含有5-20个环原子的芳基或含有5-10个环原子的杂芳基任选进一步被一个或多个以下基团取代:C1-6烷基、含有3-8个环原子的环烷基、含有3-8个环原子的杂环基、卤素、羟基、硝基或氨基。
在本发明中,“环原子数”表示原子键合成环状而得到的结构化合物(例如,单环化合物、稠环化合物、交联化合物、碳环化合物、杂环化合物)的构成该环自身的原子之中的原子数。该环被取代基所取代时,取代基所包含的原子不包括在成环原子内。关于以下所述的“环原子数”,在没有特别说明的条件下也是同样的。例如,苯环的环原子数为6,萘环的环原子数为10,噻吩基的环原子数为5。
在本发明中,“烷基”可以表示直链、支链和/或环状烷基。烷基的碳数可以为1至50、1至30、1至20、1至10或1至6。包含该术语的短语,例如,“C1-9烷基”是指包含1~9个碳原子的烷基,每次出现时,可以互相独立地为C1烷基、C2烷基、C3烷基、C4烷基、C5烷基、C6烷基、C7烷基、C8烷基或C9烷基。烷基的非限制性实例包括甲基、乙基、正丙基、异丙基、正丁基、仲丁基、叔丁基、异丁基、2-乙基丁基、3,3-二甲基丁基、正戊基、异戊基、新戊基、叔戊基、环戊基、1-甲基戊基、3-甲基戊基、2-乙基戊基、4-甲基-2-戊基、正己基、1-甲基己基、2-乙基己基、2-丁基己基、环己基、4-甲基环己基、4-叔丁基环己基、正庚基、1-甲基庚基、2,2-二甲基庚基、2-乙基庚基、2-丁基庚基、正辛基、叔辛基、2-乙基辛基、2-丁基辛基、2-己基辛基、3,7-二甲基辛基、环辛基、正壬基、正癸基、金刚烷基、2-乙基癸基、2-丁基癸基、2-己基癸基、2-辛基癸基、正十一烷基、正十二烷基、2-乙基十二烷基、2-丁基十二烷基、2-己基十二烷基、2-辛基十二烷基、正十三烷基、正十四烷基、正十五烷基、正十六烷基、2-乙基十六烷基、2-丁基十六烷基、2-己基十六烷基、2-辛基十六烷基、正十七烷基、正十八烷基、正十九烷基、正二十烷基、2-乙基二十烷基、2-丁基二十烷基、2-己基二十烷基、2-辛基二十烷基、正二十一烷基、正二十二烷基、正二十三烷基、正二十四烷基、正二十五烷基、正二十六烷基、正二十七烷基、正二十八烷基、正二十九烷基、正三十烷基、金刚烷等。
芳香基团指至少包含一个芳环的烃基。杂芳香基团指包含至少一个杂原子的芳香烃基。杂原子优选选自Si、N、P、O、S和/或Ge,特别优选选自Si、N、P、O和/或S。稠环芳香基团指芳香基团的环可以具有两个或多个环,其中两个碳原子被两个相邻的环共用,即稠环。稠杂环芳香基团指包含至少一个杂原子的稠环芳香烃基。对于本发明的目的,芳香基团或杂芳香基团不仅包括芳香环的体系,而且包含非芳香族的环系。因此,比如吡啶、噻吩、吡咯、吡唑、三唑、咪唑、噁唑、噁二唑、噻唑、四唑、吡嗪、哒嗪、嘧啶、三嗪、卡宾等体系,对于该发明目的同样认为是芳香基团或杂环芳香基团。对于本发明的目的,稠环芳香族或稠杂环芳香族环系不仅包括芳香基团或杂芳香基团的体系,而且,其中多个芳香基团或杂环芳香基团也可以被短的非芳族单元间断(<10%的非H原子,优选小于5%的非H原子,比如C、N或O原子)。因此,比如9,9'-螺二芴,9,9-二芳基芴,三芳胺,二芳基醚等体系,对于该发明目的同样认为是稠环芳香族环系。
在某个优选地实施例中,所述的芳香基团选自:苯、萘、蒽、荧蒽、菲、苯并菲、二萘嵌苯、并四苯、芘、苯并芘、苊、芴、及其衍生物;杂芳香基团选自三嗪、吡啶、嘧啶、咪唑、呋喃、噻吩、苯并呋喃、苯并噻吩、吲哚、咔唑、吡咯并咪唑、吡咯并吡咯、噻吩并吡咯、噻吩并噻吩、呋喃并吡咯、呋喃并呋喃、噻吩并呋喃、苯并异噁唑、苯并异噻唑、苯并咪唑、喹啉、异喹啉、邻二氮萘、喹喔啉、菲啶、伯啶、喹唑啉、喹唑啉酮、二苯并噻吩、二苯并呋喃、咔唑及其衍生物。
本发明中,与单键相连的“*”表示连接或稠合位点;
本发明中,基团中未指明连接位点时,表示基团中任选可连接位点作为连接位点;
本发明中,基团中未指明稠合位点时,表示基团中任选可稠合位点作为稠合位点,优选基团中处于邻位的两个或多个位点为稠合位点;
本发明提供一种醌类有机化合物,其结构如通式(I)所示:
其中:
X每次出现,分别独立地选自CR3或N;
M每次出现,分别独立地选自CR4Ar1;
Ar1每次出现,独立地选自被一个或多个R取代的具有5-60个环原子的芳香基团或杂芳香基团;所述R独立地选自D、硝基、亚硝基、CF3、Cl、Br、F、I或氰基;
R1、R2、R3、R4每次出现,分别独立选自H、D、具有1-20个碳原子的直链烷基、具有1-20个碳原子的直链烷氧基或硫代烷氧基、具有3-20个碳原子的支链或环状的烷基、具有3-20个碳原子的支链或环状的烷氧基、具有3-20个碳原子的支链或环状的硫代烷氧基、甲硅烷基、具有1-20个碳原子的酮基、具有2-20个碳原子的烷氧基羰基、具有7-20个碳原子的芳氧基羰基、氰基、氨基甲酰基、卤甲酰基、甲酰基、异氰基、异氰酸酯基、硫氰酸酯基、异硫氰酸酯基、羟基、硝基、亚硝基、烯基、CF3、C2F5、Cl、Br、F、I、可交联的基团、取代或未取代的具有5-60个环原子的芳香基团或杂芳香基团、具有5-60个环原子的芳氧基或杂芳氧基基团,或这些基团的组合;R1、R2互相成环或不成环;
在其中一个具体的实施例中,X选自N。
在一实施例中,R1、R2互相不成环;R1、R2中至少有一个选自D、硝基、亚硝基、CF3、Cl、Br、F、I、氰基、具有6-30个环原子的芳香基团或杂芳香基团、被一个或多个R’取代的具有5-30个环原子的芳香基团或杂芳香基团、具有1-20个碳原子的直链烷基、具有3-20个碳原子的支链或环状的烷基、被一个或多个R’取代的具有1-20个碳原子的直链烷基、被一个或多个R’取代的具有3-20个碳原子的支链或环状的烷基;
所述R’独立地选自D、硝基、亚硝基、CF3、C2F5、Cl、Br、F、I或氰基。
在一实施例中,R1、R2互相不成环;R1、R2分别独立地选自D、硝基、亚硝基、CF3、Cl、Br、F、I、氰基、具有5-60个环原子的芳香基团或杂芳香基团、被一个或多个R’取代的具有5-30个环原子的芳香基团或杂芳香基团、具有1-20个碳原子的直链烷基、具有3-20个碳原子的支链或环状的烷基、被一个或多个R’取代的具有1-20个碳原子的直链烷基、被一个或多个R’取代的具有3-20个碳原子的支链或环状的烷基。
在一实施例中,R1、R2分别独立地选自H、D、硝基、亚硝基、CF3、C2F5、Cl、Br、F、I或氰基或以下基团:
其中:*表示连接位点。
在一实施例中,R1、R2互相成环,所述醌类有机化合物的结构如通式(Ⅱ)所示:
其中:Ar2选自取代或未取代的具有5-60个环原子的芳香基团或杂芳香基团、取代或未取代的非芳香环系基团中的任一种。
在其中一个实施例中,所述Ar2选自如下结构中的任一种:
其中:
*表示稠合位点;
X1每次出现,独立地选自CR7或N;
Y1每次出现,独立地选自NR5、CR5R6、SiR5R6、O、S、S(=O)2或S(=O);
R5、R6、R7每次出现,分别独立选自H、D、具有1-20个碳原子的直链烷基、具有1-20个碳原子的直链烷氧基或硫代烷氧基、具有3-20个碳原子的支链或环状的烷基、具有3-20个碳原子的支链或环状的烷氧基、具有3-20个碳原子的支链或环状的硫代烷氧基、甲硅烷基、具有1-20个碳原子的酮基、具有2-20个碳原子的烷氧基羰基、具有7-20个碳原子的芳氧基羰基、氰基、氨基甲酰基、卤甲酰基、甲酰基、异氰基、异氰酸酯基、硫氰酸酯基、异硫氰酸酯基、羟基、硝基、亚硝基、烯基、CF3、C2F5、Cl、Br、F、I、可交联的基团、取代或未取代的具有5-40个环原子的芳香基团或杂芳香基团、具有5-40个环原子的芳氧基或杂芳氧基基团,或这些基团的组合。
进一步,所述Ar2选自如下结构中的任一种:
其中:
*表示稠合位点。
进一步,R7每次出现,分别独立选自H、D、硝基、亚硝基、CF3、C2F5、C3H7、C4H9、Cl、Br、F或I。
在其中一个具体的实施例中,所述M的结构如通式(Ⅲ)所示:
其中,*表示连接位点。
在其中一个具体的实施例中,所述Ar1选自如下基团的任一种:
其中:
a为1、2或3;b为1、2、3或4;c为1或2;d为1、2、3、4或5;e为1-7的任一整数;f为1-9的任一整数;
Y2每次出现,独立地选自NR8、CR8R9、SiR8R9、O、S、S(=O)2或S(=O);
R8、R9每次出现,分别独立选自H、D、具有1-20个碳原子的直链烷基、具有1-20个碳原子的直链烷氧基或硫代烷氧基、具有3-20个碳原子的支链或环状的烷基、具有3-20个碳原子的支链或环状的烷氧基、具有3-20个碳原子的支链或环状的硫代烷氧基、甲硅烷基、具有1-20个碳原子的酮基、具有2-20个碳原子的烷氧基羰基、具有7-20个碳原子的芳氧基羰基、氰基、氨基甲酰基、卤甲酰基、甲酰基、异氰基、异氰酸酯基、硫氰酸酯基、异硫氰酸酯基、羟基、硝基、亚硝基、烯基、CF3、C2F5、Cl、Br、F、I、可交联的基团、具有5-40个环原子的取代或未取代的芳香基团或杂芳香基团、具有5-40个环原子的芳氧基或杂芳氧基基团,或这些基团的组合。
在一实施例中,a为3;b为4;c为2;d为5;e为7;f为9。
在其中一个具体的实施例中,所述M选自如下结构中的任一种:
在一实施例中,R4选自D、硝基、亚硝基、CF3、Cl、Br、F、I、氰基、具有6-30个环原子的芳香基团或杂芳香基团、被一个或多个R’取代的具有5-30个环原子的芳香基团或杂芳香基团;
所述R’独立地选自D、硝基、亚硝基、CF3、C2F5、Cl、Br、F、I或氰基。
进一步,R4选自D、硝基、亚硝基、CF3、C2F5、Cl、Br、F、I、氰基或以下基团:
下面给出合适的按照本发明的醌类有机化合物的具体例子,但是不限于:
按照本发明的醌类有机化合物,可以作为功能材料用于电子器件中。有机功能材料包括,但不限于:空穴注入层(HIL)、空穴传输层(HTL)、电子传输层(ETL)、电子注入层(EIL)、电子阻挡层(EBL)、空穴阻挡层(HBL)、发光层(EML)。
在一个特别优选的实施例中,按照本发明的醌类有机化合物用于空穴注入层(HIL)或空穴传输层(HTL)中。
在一个非常优选的实施例中,按照本发明的醌类有机化合物作为p型掺杂材料用于空穴注入层(HIL)或空穴传输层(HTL)中。
在某些实施例中,按照发明的醌类有机化合物,其T1≥0.3eV,较好是≥0.6eV,最好是≥0.8eV。
作为功能材料需要好的热稳定性。一般的,按照本发明的醌类有机化合物,其玻璃化温度Tg≥100℃,在一个优选的实施例中,Tg≥120℃,在一个较为优选的实施例中,Tg≥140℃,在一个更为优选的实施例中,Tg≥160℃,在一个最为优选的实施例中,Tg≥180℃。
作为p型掺杂材料必须有适当的LUMO能级。在某些实施例中,按照发明的醌类有机化合物,其LUMO≤-5.30eV,更好是≤-5.50eV,最好是≤-5.60eV。
在某些优先的实施例中,按照本发明的醌类有机化合物,其((HOMO-(HOMO-1))≥0.2eV,较好是≥0.25eV,更好是≥0.3eV,更更好是≥0.35eV,非常好是≥0.4eV,最好是≥0.45eV。
本发明还提供一种混合物,该混合物包含如上所述的醌类有机化合物和上述的聚合物中的至少一种,及至少一种有机功能材料,所述至少一种有机功能材料可选于空穴注入材料(HIM)、空穴传输材料(HTM)、电子传输材料(ETM)、电子注入材料(EIM)、电子阻挡材料(EBM)、空穴阻挡材料(HBM)、发光材料(Emitter)、主体材料(Host)或有机染料。例如在WO2010135519A1、US20090134784A1和WO 2011110277A1中对各种有机功能材料有详细的描述,特此将此3专利文件中的全部内容并入本文作为参考。
在一些优选的实施例中,所述混合物,其中所述的另一种有机功能材料选于空穴注入材料(HIM)、空穴传输材料(HTM)或主体材料(Host)。
在某些优先的实施例中,所述混合物,其中所述的有机化合物的LUMO要等于或低于另一种有机功能材料的HOMO+0.2eV。
在某些较为优先的实施例中,所述混合物,其中所述的有机化合物的LUMO要等于或低于另一种有机功能材料的HOMO+0.1eV。
在某些特别优先的实施例中,所述混合物,其中所述的有机化合物的LUMO要等于或低于另一种有机功能材料的HOMO。
在其中一个实施例中,按照本发明的混合物包括至少一种空穴注入材料(HIM)或空穴传输材料和一种掺杂剂,所述掺杂剂是上述的醌类有机化合物,所述掺杂剂与主体的摩尔比是1:1至1:100000。
其中关于HIM/HTM/EBM,和Host(主体材料/基质材料)的详细描述详见专利WO2018095395A1。
本发明的另一个目的是为印刷OLED提供材料解决方案。
在某些实施例中,按照本发明的醌类有机化合物,其分子量≥800g/mol;优选≥900g/mol,很优选≥1000g/mol,更优选≥1100g/mol,最优选≥1200g/mol。
在另一些实施例中,按照本发明的醌类有机化合物,在25℃时,在甲苯中的溶解度≥2mg/ml,优选≥3mg/ml,更优选≥4mg/ml,最优选≥5mg/ml。
本发明还提供一种组合物,该组合物包含如上所述的醌类有机化合物或混合物中的至少一种,及至少一种有机溶剂,所述至少一种有机溶剂选自芳族或杂芳族、酯、芳族酮或芳族醚、脂肪族酮或脂肪族醚、脂环族或烯烃类化合物、硼酸酯或磷酸酯类化合物,或两种及两种以上溶剂的混合物。
在一个优选的实施例中,按照本发明的一种组合物,其特征在于,所述至少一种有机溶剂选自基于芳族或杂芳族的溶剂;
适合本发明的基于芳族或杂芳族溶剂的例子有,但不限制于:对二异丙基苯、戊苯、四氢萘、环己基苯、氯萘、1,4-二甲基萘、3-异丙基联苯、对甲基异丙苯、二戊苯、三戊苯、戊基甲苯、邻二乙苯、间二乙苯、对二乙苯、1,2,3,4-四甲苯、1,2,3,5-四甲苯、1,2,4,5-四甲苯、丁苯、十二烷基苯、二己基苯、二丁基苯、对二异丙基苯、环己基苯、苄基丁基苯、二甲基萘、3-异丙基联苯、对甲基异丙苯、1-甲基萘、1,2,4-三氯苯、4,4-二氟二苯甲烷、1,2-二甲氧基-4-(1-丙烯基)苯、二苯甲烷、2-苯基吡啶、3-苯基吡啶、N-甲基二苯胺、4-异丙基联苯、α,α-二氯二苯甲烷、4-(3-苯基丙基)吡啶、苯甲酸苄酯、1,1-双(3,4-二甲基苯基)乙烷、2-异丙基萘、喹啉、异喹啉、2-呋喃甲酸甲酯、2-呋喃甲酸乙酯等;
适合本发明的基于芳族酮溶剂的例子有,但不限制于:1-四氢萘酮,2-四氢萘酮,2-(苯基环氧)四氢萘酮,6-(甲氧基)四氢萘酮,苯乙酮、苯丙酮、二苯甲酮及它们的衍生物,如4-甲基苯乙酮、3-甲基苯乙酮、2-甲基苯乙酮、4-甲基苯丙酮、3-甲基苯丙酮、2-甲基苯丙酮等;
适合本发明的基于芳族醚溶剂的例子有,但不限制于:3-苯氧基甲苯、丁氧基苯、对茴香醛二甲基乙缩醛、四氢-2-苯氧基-2H-吡喃、1,2-二甲氧基-4-(1-丙烯基)苯、1,4-苯并二噁烷、1,3-二丙基苯、2,5-二甲氧基甲苯、4-乙基本乙醚、1,3-二丙氧基苯、1,2,4-三甲氧基苯、4-(1-丙烯基)-1,2-二甲氧基苯、1,3-二甲氧基苯、缩水甘油基苯基醚、二苄基醚、4-叔丁基茴香醚、反式-对丙烯基茴香醚、1,2-二甲氧基苯、1-甲氧基萘、二苯醚、2-苯氧基甲醚、2-苯氧基四氢呋喃、乙基-2-萘基醚。
在一些优选的实施例中,按照本发明的组合物,所述的至少一种有机溶剂可选自:脂肪族酮,例如,2-壬酮、3-壬酮、5-壬酮、2-癸酮、2,5-己二酮、2,6,8-三甲基-4-壬酮、葑酮、佛尔酮、异佛尔酮、二正戊基酮等;或脂肪族醚,例如,戊醚、己醚、二辛醚、乙二醇二丁醚、二乙二醇二乙醚、二乙二醇丁基甲醚、二乙二醇二丁醚、三乙二醇二甲醚、三乙二醇乙基甲醚、三乙二醇丁基甲醚、三丙二醇二甲醚、四乙二醇二甲醚等。
在另一些优选的实施例中,按照本发明的组合物,所述的至少一种有机溶剂可选自基于酯的溶剂:辛酸烷酯、癸二酸烷酯、硬脂酸烷酯、苯甲酸烷酯、苯乙酸烷酯、肉桂酸烷酯、草酸烷酯、马来酸烷酯、烷内酯、油酸烷酯等。特别优选辛酸辛酯、癸二酸二乙酯、邻苯二甲酸二烯丙酯、异壬酸异壬酯。
所述的溶剂可以是单独使用,也可以是作为两种或多种有机溶剂的混合物使用。
在某些优选的实施例中,按照本发明的组合物,所述至少一种有机溶剂选自:甲醇、乙醇、2-甲氧基乙醇、二氯甲烷、三氯甲烷、氯苯、邻二氯苯、四氢呋喃、苯甲醚、吗啉、甲苯、邻二甲苯、间二甲苯、对二甲苯、1,4二氧杂环己烷、丙酮、甲基乙基酮、1,2二氯乙烷、3-苯氧基甲苯、1,1,1-三氯乙烷、1,1,2,2-四氯乙烷、醋酸乙酯、醋酸丁酯、二甲基甲酰胺、二甲基乙酰胺、二甲基亚砜、四氢萘、萘烷、茚和/或它们的混合物。
一些优选的实施例中,特别适合本发明的溶剂是汉森(Hansen)溶解度参数在以下范围内的溶剂:
δd(色散力)在17.0~23.2MPa1/2的范围,尤其是在18.5~21.0MPa1/2的范围;
δp(极性力)在0.2~12.5MPa1/2的范围,尤其是在2.0~6.0MPa1/2的范围;
δh(氢键力)在0.9~14.2MPa1/2的范围,尤其是在2.0~6.0MPa1/2的范围。
按照本发明的组合物,其中有机溶剂在选取时需考虑其沸点参数。本发明中,所述的有机溶剂的沸点≥150℃;优选为≥180℃;较优选为≥200℃;更优为≥250℃;最优为≥275℃或≥300℃。这些范围内的沸点对防止喷墨印刷头的喷嘴堵塞是有益的。所述的有机溶剂可从溶剂体系中蒸发,以形成包含功能材料薄膜。
在一个优选的实施方案中,按照本发明的组合物是一溶液。
在另一个优选的实施方案中,按照本发明的组合物是一悬浮液。
溶液或悬浮液可以另外包括一个或多个组份,例如表面活性化合物、润滑剂、润湿剂、分散剂、疏水剂、粘接剂等,用于调节粘度、成膜性能、提高附着性等。
本发明实施例中的组合物中可以包括0.01-20wt%的按照本发明的醌类有机化合物或混合物,较好的是0.1-15wt%,更好的是0.2-5wt%,最好的是0.25-3wt%。
本发明还涉及所述组合物作为涂料或印刷油墨在制备有机电子器件时的用途,特别优选的是通过打印或涂布的制备方法。
其中,适合的打印或涂布技术包括(但不限于)喷墨打印、喷印(NozzlePrinting)、活版印刷、丝网印刷、浸涂、旋转涂布、刮刀涂布、辊筒印花、扭转辊印刷、平版印刷、柔版印刷、轮转印刷、喷涂、刷涂或移印、狭缝型挤压式涂布等;首选凹版印刷、喷印及喷墨印刷。
本发明还提供一种如上所述的醌类有机化合物、混合物或组合物在有机电子器件中的应用,所述的有机电子器件可选于,但不限于:有机发光二极管(OLED)、有机光伏电池(OPV)、有机发光电池(OLEEC)、有机场效应管(OFET)、有机发光场效应管、有机激光器、有机自旋电子器件、有机传感器及有机等离激元发射二极管(Organic Plasmon EmittingDiode)等,特别优选为OLED。本发明实施例中,优选将所述有机化合物或混合物或组合物用于OLED器件的空穴传输层或空穴注入层。
本发明还提供一种有机电子器件,该有机电子器件包含如上所述的醌类有机化合物或混合物中的至少一种或由上述的组合物制备而成。更进一步地,所述有机电子器件至少包含一功能层,所述功能层包含一种如上所述的醌类有机化合物或混合物;所述功能层选自空穴注入层(HIL)、空穴传输层(HTL)、发光层(EML)、电子阻挡层(EBL)、电子注入层(EIL)、电子传输层(ETL)或空穴阻挡层(HBL)。
在某个优选的实施例中,按照本发明所述的有机电子器件,至少包含一个空穴注入层或空穴传输层,所述空穴注入层或空穴传输层包含一种如上所述的醌类有机化合物。
在上述的发光器件,特别是OLED中,包括一个基片、一个阳极、至少一个发光层和一个阴极。
基片可以是不透明或透明。一个透明的基板可以用来制造一个透明的发光元器件。基片可以是刚性的或弹性的。基片可以是塑料、金属、半导体晶片或玻璃。基片最好有一个平滑的表面。无表面缺陷的基板是特别理想的选择。在一个优选的实施例中,基片是柔性的,可选于聚合物薄膜或塑料,其玻璃化温度Tg为150℃以上,较好是超过200℃,更好是超过250℃,最好是超过300℃。合适的柔性基板的例子有聚对苯二甲酸乙二醇酯(PET)和聚乙二醇(2,6-萘)(PEN)。
阳极可包括导电金属或金属氧化物,或导电聚合物。阳极可以容易地注入空穴到空穴注入层(HIL)、空穴传输层(HTL)或发光层中。在一个优选的实施例中,阳极的功函数和发光层中的发光体或作为HIL或HTL或电子阻挡层(EBL)的p型半导体材料的HOMO能级或价带能级的差的绝对值小于0.5eV,较好是小于0.3eV,最好是小于0.2eV。阳极材料的例子包括但不限于:Al、Cu、Au、Ag、Mg、Fe、Co、Ni、Mn、Pd、Pt、ITO、铝掺杂氧化锌(AZO)等。其他合适的阳极材料是已知的,本领域普通技术人员可容易地选择使用。阳极材料可以使用任何合适的技术沉积,如物理气相沉积法,包括射频磁控溅射、真空热蒸发、电子束(e-beam)等。在某些实施例中,阳极是图案结构化的。图案化的ITO导电基板可在市场上买到,并且可以用来制备根据本发明的器件。
阴极可包括导电金属或金属氧化物。阴极可以容易地注入电子到EIL或ETL或直接到发光层中。在一个优选的实施例中,阴极的功函数和发光层中发光体或作为电子注入层(EIL)或电子传输层(ETL)或空穴阻挡层(HBL)的n型半导体材料的LUMO能级或导带能级的差的绝对值小于0.5eV,较好是小于0.3eV,最好是小于0.2eV。原则上,所有可用作OLED的阴极的材料都可能作为本发明器件的阴极材料。阴极材料的例子包括但不限于:Al、Au、Ag、Ca、Ba、Mg、LiF/Al、MgAg合金、BaF2/Al、Cu、Fe、Co、Ni、Mn、Pd、Pt、ITO等。阴极材料可以使用任何合适的技术沉积,如一合适的物理气相沉积法,包括射频磁控溅射,真空热蒸发,电子束(e-beam)等。
OLED还可以包含其他功能层,如空穴注入层(HIL)、空穴传输层(HTL)、电子阻挡层(EBL)、电子注入层(EIL)、电子传输层(ETL)、空穴阻挡层(HBL)。
按照本发明的发光器件,其发光波长在300到1200nm之间,较好的是在350到1000nm之间,更好的是在400到900nm之间。
本发明还涉及按照本发明的电致发光器件在各种电子设备中的应用,包含但不限于:显示设备、照明设备、光源和传感器等。
下面将结合优选实施例对本发明进行了说明,但本发明并不局限于下述实施例,应当理解,所附权利要求概括了本发明的范围在本发明构思的引导下本领域的技术人员应意识到,对本发明的各实施例进行的一定的改变,都将被本发明的权利要求书的精神和范围所覆盖。
具体实施例
1.有机化合物的合成
合成实施例1:合成化合物1
合成中间体1-2:
将化合物1-1(10mmol),草酰氯(1.25g,10mmol),1,4-二氧六环100ml,在50℃下搅拌5小时,将反应产物冷却至室温,然后减压过滤形成的沉淀物,并向其中加入无水硫酸镁以除水分,然后减压下除去溶剂,用二氯甲烷作洗脱液使剩余物经过硅胶柱以得到产物,然后减压下除去该溶剂并在真空中干燥该产物以制备所需固体化合物1-2(6.8mmol),产率68%,MS:[M+H]+=314.2。
合成化合物1:
将化合物四氯化钛(4.67g,25mmol),1-2(10mmol),1-3(20mmol),在氮气干燥吡啶/二氯甲烷为溶剂回流搅拌24小时,之后用冷浓盐酸淬灭,二氯甲烷浓缩,之后用无水硫酸钠干燥,减压蒸馏,残余物用DCM/MeOH重结晶,得到化合物1(5.1mmol),产率51%,MS:[M+H]+=704.8。
合成实施例2:合成化合物2
合成中间体2-2:
将化合物2-1(10mmol),高锰酸钾(80mmol),1,4-二氧六环100ml,在50℃下搅拌5小时,将反应产物冷却至室温,然后减压过滤形成的沉淀物,并向其中加入无水硫酸镁以除水分,然后减压下除去溶剂,用二氯甲烷作洗脱液使剩余物经过硅胶柱以得到产物,然后减压下除去该溶剂并在真空中干燥该产物以制备所需固体化合物2-2(8.7mmol),产率87%,MS:[M+H]+=360.4。
合成化合物2:
将化合物四氯化钛(4.67g,25mmol),2-2(10mmol),2-3(20mmol),在氮气干燥吡啶/二氯甲烷为溶剂回流搅拌24小时,之后用冷浓盐酸淬灭,二氯甲烷浓缩,之后用无水硫酸钠干燥,减压蒸馏,残余物用DCM/MeOH重结晶,得到化合物2(5.4mmol),产率54%,MS:[M+H]+=824.5。
合成实施例3:合成化合物3
合成中间体3-2:
将化合物3-1(10mmol),草酰氯(1.25g,10mmol),1,4-二氧六环100ml,在50℃下搅拌5小时,将反应产物冷却至室温,然后减压过滤形成的沉淀物,并向其中加入无水硫酸镁以除水分,然后减压下除去溶剂,用二氯甲烷作洗脱液使剩余物经过硅胶柱以得到产物,然后减压下除去该溶剂并在真空中干燥该产物以制备所需固体化合物3-2(6.8mmol),产率68%,MS:[M+H]+=314.2。
合成化合物3:
将化合物四氯化钛(4.67g,25mmol),3-2(10mmol),3-3(20mmol),在氮气干燥吡啶/二氯甲烷为溶剂回流搅拌24小时,之后用冷浓盐酸淬灭,二氯甲烷浓缩,之后用无水硫酸钠干燥,减压蒸馏,残余物用DCM/MeOH重结晶,得到化合物3(5.9mmol),产率59%,MS:[M+H]+=712.6。
合成实施例4:合成化合物4
合成中间体4-2:
将化合物4-1(10mmol),草酰氯(1.25g,10mmol),1,4-二氧六环100ml,在50℃下搅拌5小时,将反应产物冷却至室温,然后减压过滤形成的沉淀物,并向其中加入无水硫酸镁以除水分,然后减压下除去溶剂,用二氯甲烷作洗脱液使剩余物经过硅胶柱以得到产物,然后减压下除去该溶剂并在真空中干燥该产物以制备所需固体化合物4-2(7.6mmol),产率76%,MS:[M+H]+=162.8。
合成化合物4:
将化合物四氯化钛(4.67g,25mmol),4-2(10mmol),4-3(20mmol),在氮气干燥吡啶/二氯甲烷为溶剂回流搅拌24小时,之后用冷浓盐酸淬灭,二氯甲烷浓缩,之后用无水硫酸钠干燥,减压蒸馏,残余物用DCM/MeOH重结晶,得到化合物4(8.1mmol),产率81%,MS:[M+H]+=632.9。
合成实施例5:合成化合物5
合成中间体5-2:
将化合物5-1(10mmol),草酰氯(1.25g,10mmol),1,4-二氧六环100ml,在50℃下搅拌5小时,将反应产物冷却至室温,然后减压过滤形成的沉淀物,并向其中加入无水硫酸镁以除水分,然后减压下除去溶剂,用二氯甲烷作洗脱液使剩余物经过硅胶柱以得到产物,然后减压下除去该溶剂并在真空中干燥该产物以制备所需固体化合物5-2(7.6mmol),产率76%,MS:[M+H]+=162.8。
合成化合物5:
将化合物四氯化钛(4.67g,25mmol),5-2(10mmol),5-3(20mmol),在氮气干燥吡啶/二氯甲烷为溶剂回流搅拌24小时,之后用冷浓盐酸淬灭,二氯甲烷浓缩,之后用无水硫酸钠干燥,减压蒸馏,残余物用DCM/MeOH重结晶,得到化合物5(6.4mmol),产率64%,MS:[M+H]+=552.1。
合成实施例6:合成化合物6
合成中间体6-2:
将化合物6-1(10mmol),草酰氯(1.25g,10mmol),1,4-二氧六环100ml,在50℃下搅拌5小时,将反应产物冷却至室温,然后减压过滤形成的沉淀物,并向其中加入无水硫酸镁以除水分,然后减压下除去溶剂,用二氯甲烷作洗脱液使剩余物经过硅胶柱以得到产物,然后减压下除去该溶剂并在真空中干燥该产物以制备所需固体化合物6-2(7.9mmol),产率79%,MS:[M+H]+=205.4。
合成化合物6:
将化合物四氯化钛(4.67g,25mmol),6-2(10mmol)6-3(20mmol),在氮气干燥吡啶/二氯甲烷为溶剂回流搅拌24小时,之后用冷浓盐酸淬灭,二氯甲烷浓缩,之后用无水硫酸钠干燥,减压蒸馏,残余物用DCM/MeOH重结晶,得到化合物6(6.1mmol),产率61%,MS:[M+H]+=587.8。
合成实施例7:合成化合物7
合成中间体7-2:
将化合物7-1(10mmol),草酰氯(1.25g,10mmol),1,4-二氧六环100ml,在50℃下搅拌5小时,将反应产物冷却至室温,然后减压过滤形成的沉淀物,并向其中加入无水硫酸镁以除水分,然后减压下除去溶剂,用二氯甲烷作洗脱液使剩余物经过硅胶柱以得到产物,然后减压下除去该溶剂并在真空中干燥该产物以制备所需固体化合物7-2(5.7mmol),产率57%,MS:[M+H]+=214.3。
合成化合物7:
将化合物四氯化钛(4.67g,25mmol),7-2(10mmol)7-3(20mmol),在氮气干燥吡啶/二氯甲烷为溶剂回流搅拌24小时,之后用冷浓盐酸淬灭,二氯甲烷浓缩,之后用无水硫酸钠干燥,减压蒸馏,残余物用DCM/MeOH重结晶,得到化合物7(4.9mmol),产率49%,MS:[M+H]+=590.2。
合成实施例8:合成化合物8
合成中间体8-2:
将化合物8-1(10mmol),草酰氯(1.25g,10mmol),1,4-二氧六环100ml,在50℃下搅拌5小时,将反应产物冷却至室温,然后减压过滤形成的沉淀物,并向其中加入无水硫酸镁以除水分,然后减压下除去溶剂,用二氯甲烷作洗脱液使剩余物经过硅胶柱以得到产物,然后减压下除去该溶剂并在真空中干燥该产物以制备所需固体化合物8-2(6.8mmol),产率68%,MS:[M+H]+=312.5。
合成化合物8:
将化合物四氯化钛(4.67g,25mmol),8-2(10mmol)8-3(20mmol),在氮气干燥吡啶/二氯甲烷为溶剂回流搅拌24小时,之后用冷浓盐酸淬灭,二氯甲烷浓缩,之后用无水硫酸钠干燥,减压蒸馏,残余物用DCM/MeOH重结晶,得到化合物8(5.7mmol),产率57%,MS:[M+H]+=612.1。
合成实施例9:合成化合物9
合成中间体9-2:
将化合物9-1(10mmol),草酰氯(1.25g,10mmol),1,4-二氧六环100ml,在50℃下搅拌5小时,将反应产物冷却至室温,然后减压过滤形成的沉淀物,并向其中加入无水硫酸镁以除水分,然后减压下除去溶剂,用二氯甲烷作洗脱液使剩余物经过硅胶柱以得到产物,然后减压下除去该溶剂并在真空中干燥该产物以制备所需固体化合物9-2(5.3mmol),产率53%,MS:[M+H]+=166.7。
合成化合物9:
将化合物四氯化钛(4.67g,25mmol),9-2(10mmol)9-3(20mmol),在氮气干燥吡啶/二氯甲烷为溶剂回流搅拌24小时,之后用冷浓盐酸淬灭,二氯甲烷浓缩,之后用无水硫酸钠干燥,减压蒸馏,残余物用DCM/MeOH重结晶,得到化合物9(6.7mmol),产率67%,MS:[M+H]+=556.4。
合成实施例10:合成化合物10
合成中间体10-2:
将化合物10-1(10mmol),草酰氯(1.25g,10mmol),1,4-二氧六环100ml,在50℃下搅拌5小时,将反应产物冷却至室温,然后减压过滤形成的沉淀物,并向其中加入无水硫酸镁以除水分,然后减压下除去溶剂,用二氯甲烷作洗脱液使剩余物经过硅胶柱以得到产物,然后减压下除去该溶剂并在真空中干燥该产物以制备所需固体化合物10-2(8.1mmol),产率81%,MS:[M+H]+=248.7。
合成化合物10:
将化合物四氯化钛(4.67g,25mmol),10-2(10mmol)10-3(20mmol),在氮气干燥吡啶/二氯甲烷为溶剂回流搅拌24小时,之后用冷浓盐酸淬灭,二氯甲烷浓缩,之后用无水硫酸钠干燥,减压蒸馏,残余物用DCM/MeOH重结晶,得到化合物10(3.9mmol),产率39%,MS:[M+H]+=766.1。
对比实施例1:合成对比化合物1
合成对比化合物1-2:
将对比化合物1-1(10mmol),2-溴,2-氯丙烷(20mmol),醋酸钯(0.02mmol),碳酸钾(40mmol)1,4-二氧六环100ml,80℃下搅拌5小时,将反应产物冷却至室温,然后减压过滤形成的沉淀物,并向其中加入无水硫酸镁以除水分,然后减压下除去溶剂,用二氯甲烷作为洗脱液使剩余物经过硅胶柱以得到产物,然后减压下除去该溶剂并在真空中干燥该产物以制备所需固体对比化合物1-2(8.5mmol),产率85%,MS:[M+H]+=280.3。
合成对比化合物1:
将化合物氢氧化钾(50mmol),对比化合物1-2(10mmol),在氮气干燥乙醇为溶剂回流搅拌24小时,之后用冷浓盐酸淬灭,二氯甲烷浓缩,之后用无水硫酸钠干燥,减压蒸馏,残余物用DCM/MeOH重结晶,得到对比化合物1(5.9mmol),产率59%,MS:[M+H]+=210.1。
2、化合物的能级计算
有机化合物材料的能级可通过量子计算得到,比如利用TD-DFT(含时密度泛函理论)通过Gaussian09W(Gaussian Inc.),具体的模拟方法可参见WO2011141110。首先用半经验方法“Ground State/Semi-empirical/Default Spin/AM1”(Charge 0/Spin Singlet)来优化分子几何结构,然后有机分子的能量结构由TD-DFT(含时密度泛函理论)方法算得“TD-SCF/DFT/Default Spin/B3PW91”与基组“6-31G(d)”(Charge 0/Spin Singlet)。HOMO和LUMO能级按照下面的校准公式计算,S1,T1和谐振因子f(S1)直接使用。
HOMO(eV)=((HOMO(G)×27.212)-0.9899)/1.1206
LUMO(eV)=((LUMO(G)×27.212)-2.0041)/1.385
其中HOMO(G)和LUMO(G)是Gaussian 09W的直接计算结果,单位为Hartree。结果如表一所示:
表一
材料 | HOMO[eV] | LUMO[eV] | T<sub>1</sub>[eV] | S<sub>1</sub>[eV] |
化合物1 | -7.01 | -5.04 | 0.94 | 2.14 |
化合物2 | -7.05 | -5.07 | 0.87 | 2.12 |
化合物3 | -6.93 | -5.21 | 0.92 | 1.54 |
化合物4 | -7.21 | -5.07 | 0.81 | 1.68 |
化合物5 | -7.14 | -5.14 | 0.86 | 1.96 |
化合物6 | -6.87 | -5.08 | 0.75 | 2.51 |
化合物7 | -7.10 | -5.03 | 0.71 | 2.22 |
化合物8 | -7.04 | -5.14 | 0.89 | 1.96 |
化合物9 | -7.05 | -5.02 | 0.92 | 1.91 |
化合物10 | -6.95 | -5.21 | 0.96 | 2.01 |
对比化合物1 | -5.42 | -2.37 | 2.16 | 2.34 |
3.OLED器件的制备和表征:
器件的具体结构如下:
ITO/HI(10nm)/HT-1(120nm)/HT-2(10nm)/BH:BD(25nm)/ET:Liq30nm)/Liq(1nm)/Al(100nm);
器件各层所使用的材料如下:
OLED器件的制备步骤如下:
a、导电玻璃基片的清洗:首次使用时,可用多种溶剂进行清洗,例如氯仿、酮、异丙醇进行清洗,然后进行紫外臭氧等离子处理;
b、HI(10nm),HT-1(120nm),HT-2(10nm),EML(20nm),ETL(30nm):将ITO基片移入真空气相沉积设备中,在高真空(1×10-6毫巴)下,采用电阻加热蒸发,HT-1和化合物1以98:2的比例共蒸镀形成10nm的注入层,之后依次蒸镀得到120nm的HT-1以及10nm的HT-2层。随后BH和BD以97:3的比例共蒸镀形成25nm的发光层。接着将ET和Liq置于不同的蒸发单元,使其分别以50重量%的比例进行共沉积,在发光层上形成30nm的电子传输层,随后在电子传输层上沉积1nm的Liq作为电子注入层,最后在所述电子注入层上沉积厚度为100nm的Al阴极;
c、封装:器件在氮气手套箱中用紫外线硬化树脂封装。
所有器件除了HI采用不同的化合物作为掺杂剂,其他实施方案均相同。各OLED器件的电流电压(J-V)特性通过表征设备来表征,同时记录重要的参数如启动电压、效率及寿命,具体如表二所示:
表二
经检测后,采用化合物1-10作为HIL层的掺杂剂,所得到器件所需电压较低,效率和寿命相比对比化合物1都有明显的提高。
以上所述实施例的各技术特征可以进行任意的组合,为使描述简洁,未对上述实施例中的各个技术特征所有可能的组合都进行描述,然而,只要这些技术特征的组合不存在矛盾,都应当认为是本说明书记载的范围。
以上所述实施例仅表达了本发明的几种实施方式,其描述较为具体和详细,但并不能因此而理解为对发明专利范围的限制。应当指出的是,对于本领域的普通技术人员来说,在不脱离本发明构思的前提下,还可以做出若干变形和改进,这些都属于本发明的保护范围。因此,本发明专利的保护范围应以所附权利要求为准。
Claims (12)
1.一种醌类有机化合物,其特征在于,其结构如通式(I)所示:
其中:
X每次出现,分别独立地选自CR3或N;
M每次出现,分别独立地选自CR4Ar1;
Ar1每次出现,独立地选自被一个或多个R取代的具有5-60个环原子的芳香基团或杂芳香基团;所述R独立地选自D、硝基、亚硝基、CF3、Cl、Br、F、I或氰基;
R1、R2、R3、R4每次出现,分别独立选自H、D、具有1-20个碳原子的直链烷基、具有1-20个碳原子的直链烷氧基或硫代烷氧基、具有3-20个碳原子的支链或环状的烷基、具有3-20个碳原子的支链或环状的烷氧基、具有3-20个碳原子的支链或环状的硫代烷氧基、甲硅烷基、具有1-20个碳原子的酮基、具有2-20个碳原子的烷氧基羰基、具有7-20个碳原子的芳氧基羰基、氰基、氨基甲酰基、卤甲酰基、甲酰基、异氰基、异氰酸酯基、硫氰酸酯基、异硫氰酸酯基、羟基、硝基、亚硝基、烯基、CF3、C2F5、Cl、Br、F、I、可交联的基团、取代或未取代的具有5-60个环原子的芳香基团或杂芳香基团、具有5-60个环原子的芳氧基或杂芳氧基基团,或这些基团的组合;R1、R2互相成环或不成环。
2.根据权利要求1所述的醌类有机化合物,其特征在于,X选自N。
3.根据权利要求1所述的醌类有机化合物,其特征在于,R1、R2互相不成环;
R1、R2中至少有一个选自D、硝基、亚硝基、CF3、Cl、Br、F、I、氰基、具有6-30个环原子的芳香基团或杂芳香基团、被一个或多个R’取代的具有5-30个环原子的芳香基团或杂芳香基团、具有1-20个碳原子的直链烷基、具有3-20个碳原子的支链或环状的烷基、被一个或多个R’取代的具有1-20个碳原子的直链烷基、被一个或多个R’取代的具有3-20个碳原子的支链或环状的烷基;
所述R’独立地选自D、硝基、亚硝基、CF3、C2F5、Cl、Br、F、I或氰基。
6.根据权利要求5所述的醌类有机化合物,其特征在于,所述Ar2选自如下结构中的任一种:
其中:
*表示稠合位点;
X1每次出现,独立地选自CR7或N;
Y1每次出现,独立地选自NR5、CR5R6、SiR5R6、O、S、S(=O)2或S(=O);
R5、R6、R7每次出现,分别独立选自H、D、具有1-20个碳原子的直链烷基、具有1-20个碳原子的直链烷氧基或硫代烷氧基、具有3-20个碳原子的支链或环状的烷基、具有3-20个碳原子的支链或环状的烷氧基、具有3-20个碳原子的支链或环状的硫代烷氧基、甲硅烷基、具有1-20个碳原子的酮基、具有2-20个碳原子的烷氧基羰基、具有7-20个碳原子的芳氧基羰基、氰基、氨基甲酰基、卤甲酰基、甲酰基、异氰基、异氰酸酯基、硫氰酸酯基、异硫氰酸酯基、羟基、硝基、亚硝基、烯基、CF3、C2F5、Cl、Br、F、I、可交联的基团、取代或未取代的具有5-40个环原子的芳香基团或杂芳香基团、具有5-40个环原子的芳氧基或杂芳氧基基团,或这些基团的组合。
8.根据权利要求1-7任一项所述的醌类有机化合物,其特征在于,所述M的结构如通式(Ⅲ)所示:
其中,*表示连接位点;
所述Ar1选自如下基团的任一种:
其中:
a为1、2或3;b为1、2、3或4;c为1或2;d为1、2、3、4或5;e为1-7的任一整数;f为1-9的任一整数;
Y2每次出现,独立地选自NR8、CR8R9、SiR8R9、O、S、S(=O)2或S(=O);
R8、R9每次出现,分别独立选自H、D、具有1-20个碳原子的直链烷基、具有1-20个碳原子的直链烷氧基或硫代烷氧基、具有3-20个碳原子的支链或环状的烷基、具有3-20个碳原子的支链或环状的烷氧基、具有3-20个碳原子的支链或环状的硫代烷氧基、甲硅烷基、具有1-20个碳原子的酮基、具有2-20个碳原子的烷氧基羰基、具有7-20个碳原子的芳氧基羰基、氰基、氨基甲酰基、卤甲酰基、甲酰基、异氰基、异氰酸酯基、硫氰酸酯基、异硫氰酸酯基、羟基、硝基、亚硝基、烯基、CF3、C2F5、Cl、Br、F、I、可交联的基团、具有5-40个环原子的取代或未取代的芳香基团或杂芳香基团、具有5-40个环原子的芳氧基或杂芳氧基基团,或这些基团的组合。
10.一种混合物,其特征在于,所述混合物包含如权利要求1-9任一项所述的醌类有机化合物中的至少一种,及至少一种有机功能材料,所述的有机功能材料选自空穴注入材料、空穴传输材料、电子传输材料、电子注入材料、电子阻挡材料、空穴阻挡材料、发光材料、主体材料或有机染料。
11.一种组合物,其特征在于,所述组合物包含如权利要求1-9任一项所述的醌类有机化合物、权利要求10所述的混合物中的至少一种,及至少一种有机溶剂。
12.一种有机电子器件,其特征在于,所述有机电子器件包含权利要求1-9任一项所述的醌类有机化合物、权利要求10所述的混合物中的至少一种或由权利要求11所述的组合物制备而成。
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