CN111004168A - 有机化合物及使用其的有机电激发光组件 - Google Patents
有机化合物及使用其的有机电激发光组件 Download PDFInfo
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- CN111004168A CN111004168A CN201910951538.3A CN201910951538A CN111004168A CN 111004168 A CN111004168 A CN 111004168A CN 201910951538 A CN201910951538 A CN 201910951538A CN 111004168 A CN111004168 A CN 111004168A
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 51
- 239000000463 material Substances 0.000 claims abstract description 52
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 44
- 125000003118 aryl group Chemical group 0.000 claims description 41
- -1 amino, silyl Chemical group 0.000 claims description 38
- 150000001875 compounds Chemical class 0.000 claims description 35
- 125000001072 heteroaryl group Chemical group 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 29
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- 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 125000000304 alkynyl group Chemical group 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 14
- 125000001769 aryl amino group Chemical group 0.000 claims description 12
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 12
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 10
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 10
- 229910052805 deuterium Inorganic materials 0.000 claims description 10
- 125000004104 aryloxy group Chemical group 0.000 claims description 9
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 9
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims description 5
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- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims description 4
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 claims description 4
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical group C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 3
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
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- 125000005331 diazinyl group Chemical group N1=NC(=CC=C1)* 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 3
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- ASUOLLHGALPRFK-UHFFFAOYSA-N phenylphosphonoylbenzene Chemical group C=1C=CC=CC=1P(=O)C1=CC=CC=C1 ASUOLLHGALPRFK-UHFFFAOYSA-N 0.000 claims 1
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
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- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 125000000623 heterocyclic group Chemical group 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 6
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 6
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 6
- DDGPPAMADXTGTN-UHFFFAOYSA-N 2-chloro-4,6-diphenyl-1,3,5-triazine Chemical compound N=1C(Cl)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 DDGPPAMADXTGTN-UHFFFAOYSA-N 0.000 description 5
- 125000005264 aryl amine group Chemical group 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- 238000005401 electroluminescence Methods 0.000 description 5
- 230000005525 hole transport Effects 0.000 description 5
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- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
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- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 4
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 4
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 238000007740 vapor deposition Methods 0.000 description 4
- TUGMGVWOTWPOET-UHFFFAOYSA-N (2-phenylnaphthalen-1-yl)boronic acid Chemical compound C1=CC2=CC=CC=C2C(B(O)O)=C1C1=CC=CC=C1 TUGMGVWOTWPOET-UHFFFAOYSA-N 0.000 description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 3
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 3
- LONBOJIXBFUBKQ-UHFFFAOYSA-N 2,7-dibromo-9,9-dimethylfluorene Chemical compound C1=C(Br)C=C2C(C)(C)C3=CC(Br)=CC=C3C2=C1 LONBOJIXBFUBKQ-UHFFFAOYSA-N 0.000 description 3
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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- 125000003277 amino group Chemical group 0.000 description 2
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- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 2
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- 238000004140 cleaning Methods 0.000 description 1
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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 1
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- BNASDYJRNOLPQY-UHFFFAOYSA-N iridium 2-phenylquinoline Chemical compound [Ir].c1ccc(cc1)-c1ccc2ccccc2n1.c1ccc(cc1)-c1ccc2ccccc2n1.c1ccc(cc1)-c1ccc2ccccc2n1 BNASDYJRNOLPQY-UHFFFAOYSA-N 0.000 description 1
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- YGNUPJXMDOFFDO-UHFFFAOYSA-N n,4-diphenylaniline Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1NC1=CC=CC=C1 YGNUPJXMDOFFDO-UHFFFAOYSA-N 0.000 description 1
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- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 125000006413 ring segment Chemical group 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
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 239000001632 sodium acetate Substances 0.000 description 1
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- 239000007787 solid Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
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- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—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
- 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
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- 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
- C07D241/46—Phenazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/62—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with more than three condensed rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/62—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with more than three condensed rings
- C07C13/66—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with more than three condensed rings the condensed ring system contains only four rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
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Abstract
本发明提供了可在有机电激发光组件中用作发光层的磷光主体材料、荧光主体材料、或荧光掺杂剂材料、和/或电子传输材料的有机化合物。采用该有机化合物的有机电激发光组件可以降低驱动电压、延长半衰期、或提高电流效率。
Description
技术领域
本发明是关于一种新颖的有机化合物,更具体言之是关于一种使用该有机化合物的有机电激发光组件。
背景技术
有机电激发光(下文称为有机EL)组件是一种有机发光二极管(OLED),其中发光层是由有机化合物制成的膜,有机化合物可回应电流而发光。包含有机化合物的发光层被夹置于两个电极之间。有机EL组件由于其高照度、重量轻、超薄外形、自照明而无需背光、低功耗、广视角、高对比度、制造方法简单和反应时间快速而被应用于平板显示器。
典型上,有机EL组件是由位于两个电极之间的有机材料层构成。有机材料层包括例如电洞注入层(HIL)、电洞传输层(HTL)、发光层(EML)、电子传输层(ETL)、和电子注入层(EIL)。有机电激发光的基本原理涉及载子(carrier)的注入、传输、和复合、并且激子(exciton)的形成,以进行发光。当施加外部电压到有机EL组件时,电子和电洞分别从阴极和阳极注入。电子从阴极注入LUMO(最低未占用分子轨域)中,而电洞从阳极注入HOMO(最高占用分子轨域)中。随后,电子在发光层中与电洞重组而形成激子,然后激子失活而发光。当发光分子吸收能量而达到激发态时,依据电子和电洞的自旋组合,激子可呈单重态或三重态。众所周知,在电激发下形成的激子通常包括25%的单重态激子和75%的三重态激子。然而,在荧光材料中,75%的三重态激子中的电生成能量将作为热量消散,因为从三重态衰减是自旋禁阻(spin forbidden)的。因此,荧光电激发光组件仅具有25%的内部量子效率(internal quantum efficiency),导致理论上最高的外部量子效率(EQE)仅有5%,因为组件的光输出耦合效率只有约20%。相较于荧光电激发光组件,磷光有机EL组件利用自旋─轨域相互作用(spin-orbit interaction)来促进单重态与三重态之间的系统间穿越(intersystem crossing),因此来自单重态和三重态的发光皆可取得,而且电激发光组件的内部量子效率可自25%升至100%。
对于使用有机EL组件的全彩平板显示器而言,有机EL组件中使用的有机材料,在驱动电压、发光效率或半衰期等方面,仍不尽理想,对于工业实施的用途仍有缺失。所以,有必要提出一种有机化合物,在延长半衰期、降低驱动电压、或提高电流效率等等任何一方面,有所改善,如此有助于有机EL组件等相关产业的技术提升。
发明内容
因此,本发明的目的之一是提供一种有机化合物,和使用该有机化合物的有机电激发光组件,其可以较低的驱动电压运作,或者操作出较高的电流效率,或较长的半衰期。
本发明的另一个目的是提供一种有机化合物,和使用该有机化合物的有机电激发光组件,其可在较低的电压下操作,并具有更高的电流效率和更长的半衰期。
本发明的又一个目的是提供一种有机化合物,其可以用作发光层中的磷光主体材料,荧光主体材料、或荧光荧光掺杂剂材料,和/或用作发光层中的电子传输材料。该有机电激发光组件以改善功耗,亮度,电流效率或使用寿命。
为达到上述目的,本发明采用以下技术方案:
一种可用于有机EL组件的有机化合物。该有机化合物是由下式(1)表示:
其中C1至C4或C5至C8四个碳原子里的两个连续碳原子,与下式(3)的结构稠合:
其中X是二价桥选自于由O、S、NR4、CR5R6、及SiR7R8组成的群组;
其中R4选自于由芳基、杂芳基、芳胺基、杂芳胺基、和其组合组成的群组;
其中R5至R8独立的选自于由烷基、芳基、芳烷基、杂芳基、和其组合组成的群组;
其中R9至R12独立地选自于由卤素、芳基、杂芳基、芳胺基、杂芳胺基、氘、烷基、环烷基、杂烷基、杂环烷基、芳烷基、烷氧基、芳氧基、氨基、硅烷基、烯基、环烯基、杂烯基、炔基、羰基、羧酸、醚、酯、二醇、异腈、硫基、亚磺酰胺、磺酰基、磷酸基、和其组合组成的群组;并且
其中每个R1至R3、和R9至R12独立表示氢、不存在、或取代物独立地选自于由卤素、芳基、杂芳基、芳胺基、杂芳胺基、氘、烷基、环烷基、杂烷基、杂环烷基、芳烷基、烷氧基、芳氧基、氨基、硅烷基、烯基、环烯基、杂烯基、炔基、羰基、羧酸、醚、酯、二醇、异腈、硫基、亚磺酰胺、磺酰基、磷酸基、和其组合组成的群组;
其中R9与R10可接合在一起,或R11与R12可接合在一起,以形成苯环。
本发明进一步提供一种有机电激发光组件。该有机电激发光组件(有机EL组件)包含由阴极和阳极组成的电极对、和在该电极对之间的发光层和一个或多个有机薄膜层。该发光层和该有机薄膜层中的至少一个包含式(1)的有机化合物。本发明使用式(1)的有机化合物作为发光层的材料(掺杂剂或主体),可使有机EL组件在相同电压(例如6V)下具有更高的亮度(例如998~1584cd/m2)或电流效率(例如5.13~8.21cd/A)、或更长的半衰期(例如314~492小时)。本发明的有机EL组件使用式(1)的有机化合物作为电子传输材料,可具有降低的驱动电压(例如约4.5~5.8V)、更低的功耗、更高的电流效率(例如约7.43~8.61cd/A)、更长的半衰期(例如约415~490小时)。
附图说明
图1显示本发明的有机EL组件的一个实施例;
图中的标号如下所示:
10透明电极 20电洞注入层
30电洞传输层 40发光层
50电子传输层 60电子注入层
70金属电极。
具体实施方式
本发明探究有机化合物和使用该有机化合物的有机电激发光组件。下面将详细说明生产、结构和组成部分,以使本发明可被充分理解。本发明的应用显然不受限于所属技术领域普通技术人员熟知的具体细节。另一方面,不对众所周知的一般组成部分和过程作详细描述,以避免对本发明造成不必要的限制。现在将在下面更详细地描述本发明的一些较佳实施例。然而,应当理解的是,除了本文明确描述的实施例之外,本发明还可实施于各种其他实施例中,也就是说,本发明还可被广泛应用于其他实施例,且本发明的范围不会因此受到明确的限制,只受随附申请专利范围的内容限制。
如本说明书所示,用语「卤素」或「卤基」包括氟、氯、溴和碘。
如本说明书所示,如果是用来表达数量(例如几个)用语「第一个整数至第二个整数」可以是指第一个整数、第二个整数、和两个整数之间的「每一个」整数。例如,1至4包括1、2、3、4。又例如,0至3包括0、1、2、3。
如本说明书所示,用语「烷基」可以是指直链和/或分支链烷基。烷基系可以是含有1至30个碳原子的烷基,较佳1至20个碳原子的烷基,更佳1至12个碳原子的烷基。适合的烷基例如甲基、乙基、丙基、1-甲基乙基、丁基、1-甲基丙基、2-甲基丙基、戊基、1-甲基丁基、2-甲基丁基、3-甲基丁基、1,1-二甲基丙基、1,2-二甲基丙基、2,2-二甲基丙基和其类似基团。另外,烷基可视情况经取代。
如本说明书所示,用语「烷氧基」是指烷基与氧原子连结后所生成的基团,最简单的是甲氧基(-OCH3)。烷氧基可以是含有1至30个碳原子的烷氧基,较佳1至20个碳原子的烷氧基,更佳1至12个碳原子的烷氧基。另外,烷氧基可视情况经取代。
如本说明书所示,用语「芳基」或「芳族基团」可以是指单环芳族基团和/或多环芳族基团。多环芳族基团可以是有两个或更多个的环,其中两个邻接环共享两个碳(此时称该基团为「稠合的」)。在多环芳族基团,该等环中的至少一个是芳族的,其他环可为环烷基、环烯基、芳基、杂环和/或杂芳基。芳基可以是含有6至30个碳原子、较佳6至20个碳原子、更佳6至12个碳原子的芳基。尤佳的为具有6个碳、10个碳或12个碳的芳基。适合芳基包括苯基、联苯、联三苯、联伸三苯、联伸四苯、萘、蒽、萉、菲、茀、芘、苝和薁,较佳苯基、联苯、联三苯、联伸三苯、茀和萘。另外,芳基可视情况经取代。
如本说明书所示,用语「芳胺基」可以是指的具有至少有一芳基键结在氮原子上的胺基。芳胺基可以是含有5至30个环碳原子、较佳5至20个环碳原子、更佳5至12个环碳原子的芳胺基。尤佳的为具有5个环碳、9个环碳或11个环碳的芳胺基。另外,芳胺基可视情况经取代。
如本说明书所示,用语「芳烷基」或「芳基烷基」可互换地使用且涵盖具有芳族基团作为取代基的烷基。芳烷基可以是含有6至30个碳原子、较佳6至20个碳原子、更佳6至12个碳原子的芳烷基。尤佳的为具有6个碳、10个碳或12个碳的芳基。另外,芳烷基可视情况经取代。
如本说明书所示,用语「杂芳基」可包括1至5个杂原子的单环杂芳族基团。用语「杂芳基」亦可包括具有两个或更多个环的多环杂芳族基团,其中两个邻接环共享两个碳(此时称该基团为「稠合的」),其中该等环中的至少一者系杂芳基,其他环可以例如是环烷基、环烯基、芳基、杂环和/或杂芳基。杂芳基可以是含有3至30个碳原子、较佳3至20个碳原子、更佳3至12个碳原子的杂芳基。适合杂芳基包括二苯并噻吩、二苯并呋喃、二苯并硒吩、呋喃、噻吩、苯并呋喃、苯并噻吩、苯并硒吩、咔唑、吲哚并咔唑、吡啶基吲哚、吡咯并二吡啶、吡唑、咪唑、三唑、恶唑、噻唑、恶二唑、恶三唑、二恶唑、噻二唑、吡啶、哒嗪、嘧啶、吡嗪、三嗪、恶嗪、恶噻嗪、恶二嗪、吲哚、苯并咪唑、吲唑、吲哚嗪、苯并恶唑、苯并异恶唑、苯并噻唑、喹啉、异喹啉、啉、喹唑啉、喹喏啉、啶、酞嗪、喋啶、二苯并哌喃(xanthene)、吖啶、吩嗪、啡噻嗪、啡恶嗪、苯并呋喃并吡啶、呋喃并二吡啶、苯并噻吩并吡啶、噻吩并二吡啶、苯并硒吩并吡啶和硒吩并二吡啶,较佳二苯并噻吩、二苯并呋喃、二苯并硒吩、咔唑、吲哚并咔唑、咪唑、吡啶、三嗪、苯并咪唑、1,2-氮杂硼烷、1,3-氮杂硼烷、1,4-氮杂硼烷、硼氮炔和其氮杂类似物。另外,杂芳基可视情况经取代。
如本说明书所示,用语「杂芳胺基」可以是指的具有至少有一芳基附接在氮原子上的胺基。杂芳胺基可以含有5至30个环碳原子、较佳5至20个环碳原子、更佳5至12个环碳原子的杂芳胺基。尤佳的为具有5个环碳、9个环碳或11个环碳的杂芳胺基。另外,杂芳胺基可视情况经取代。
如本说明书所示,「取代」或「经取代」表示除H(氢)以外的「取代物」键结至相关位置,例如键结至碳或氮。据此,举例来说,在以R表示经单取代时,则一个R必须不为H。类似地,在以R表示经至少两个取代时,则两个R必须不为H。类似地,在R未经取代时,R对于所有可用位置而言均为氢。结构(例如,特定环)中可能的最大数目个取代,可以视具有可用化合价的原子数而定。此外,在以Q或R表示取代时(可以是R1、R2…或RN),Q或R可以是卤素、烷基、环烷基、杂环烷基、芳基、芳族基团、芳烷基、杂芳基、芳胺基、杂芳胺基、氘、烷氧基、氨基、硅烷基、苯基、联苯基、芴基、苯并芴基、萘基、蒽基、菲基、芘基、烯基、环烯基、杂烯基、炔基、羰基、羧酸、醚、酯、二醇、异腈、硫基、亚磺酰胺、磺酰基、磷酸基、三亚苯基、苯并咪唑基、咔唑基、双咔唑基、二苯并呋喃基、二苯并噻吩基、二苯基氧化膦基、三嗪基、二嗪基、吡啶基、菲咯啉基团、二氢吖啶基、吩噻嗪基、吩恶嗪基、二氢吩嗪基、二苯胺基、三苯胺基、苯基二苯并呋喃基胺基、苯基二苯并硫代苯胺基、或其组合。另外,在以R表示经两个取代时,两个取代基可选择性地连接成一单环或多环芳族基团(与被取代者共同构成)。
多环芳族基团(polycyclic aromatic group)可能具有两个或更多个可能被取代的环。在这种情况下,可以绘制一条长直线以通过化学式中的该些可能被取代的环。以下列化学式为示例:
应理解的是,当将分子片段描述为取代基,或描述为连接至另一部分时,其名称可书写为如同其为片段(例如苯基、伸苯基、萘基、二苯并呋喃基)一般,或可书写为如同其为整个分子(例如苯、萘、二苯并呋喃)。如本说明书所示,此等取代基、连接片段、或整个分子所书写出来的不同名称,实际上是视为等效,而可以彼此替换的。
如本说明书所示,用语「环烷基」可以是指环状烷基。较佳之环烷基系含有3至10个环碳原子之环烷基,且包括环丙基、环戊基、环己基、金刚烷基和其类似基团。另外,环烷基可视情况经取代。
如本说明书所示,用语「烯基」可以是指直链和/或分支链烯基。较佳之烯基系含有2至15个碳原子之烯基。另外,烯基可视情况经取代。
如本说明书所示,用语「炔基」可以是指直链和/或分支链炔基。较佳之炔基系含有2至15个碳原子之炔基。另外,炔基可视情况经取代。
如本说明书所示,用语「杂环基」可以是指芳族和/或非芳族环状基团。芳族杂环基也可以意指杂芳基。较佳的非芳族杂环基系含有包括至少一个杂原子的3至7个环原子的杂环基,且包括环胺,诸如吗啉基、哌啶基、吡咯啶基和其类似物,和环醚,诸如四氢呋喃、四氢哌喃和其类似物。另外,杂环基可视情况经取代。
烷基、烷氧基、芳基、芳烷基、杂芳基、环烷基、烯基、炔基、芳烷基、和杂环基可未经取代或可经一或多个选自由以下组成之群组的取代基取代:氘、卤素、烷基、环烷基、杂烷基、芳烷基、烷氧基、芳氧基、胺基、环胺基、硅烷基、烯基、环烯基、杂烯基、炔基、芳基、杂芳基、酰基、羰基、羧酸、醚、酯、腈、异腈、硫基、亚磺酰基、磺酰基、膦基、和其组合。
在本发明的一个实施例中,提供了可以在有机EL组件中用作发光层的磷光主体材料、荧光主体材料、或荧光掺杂剂材料、和/或电子传输材料的有机化合物。该有机化合物是由下式(1)表示:
其中C1至C4或C5至C8四个碳原子里的两个连续碳原子,与下式(3)的结构稠合:
其中X是二价桥选自于由O、S、NR4、CR5R6、及SiR7R8组成的群组;
其中R4选自于由芳基、杂芳基、芳胺基、杂芳胺基、和其组合组成的群组;
其中R5至R8独立地选自于由烷基、芳基、芳烷基、杂芳基、和其组合组成的群组;
其中R9至R12独立地选自于由卤素、芳基、杂芳基、芳胺基、杂芳胺基、氘、烷基、环烷基、杂烷基、杂环烷基、芳烷基、烷氧基、芳氧基、氨基、硅烷基、烯基、环烯基、杂烯基、炔基、羰基、羧酸、醚、酯、二醇、异腈、硫基、亚磺酰胺、磺酰基、磷酸基、和其组合组成的群组;并且
其中每个R1至R3、和R9至R12独立表示氢、不存在、或取代物独立地选自于由卤素、芳基、杂芳基、芳胺基、杂芳胺基、氘、烷基、环烷基、杂烷基、杂环烷基、芳烷基、烷氧基、芳氧基、氨基、硅烷基、烯基、环烯基、杂烯基、炔基、羰基、羧酸、醚、酯、二醇、异腈、硫基、亚磺酰胺、磺酰基、磷酸基、和其组合组成的群组,且其中每个R1至R3表示的取代物在其附接的环碳原子上是单取代到可能的最大数目个取代;
其中R9与R10可接合在一起,或R11与R12可接合在一起,以形成苯环。
在某些实施例中,本发明有机化合物是由下式(2)和式(22)其中之一表示:
其中Q表示以下式(3):
X是选自于由O、S、NR4、CR5R6、和SiR7R8组成之群组的二价桥;
R1至R3独立表示不存在、氢原子或取代物选自于由卤素、具有5至30个环碳原子的经取代或未经取代芳基、具有5至30个环碳原子的经取代或未经取代杂芳基、具有5至30个环碳原子的经取代或未经取代芳胺基、和5至30个环碳原子的经取代或未经取代杂芳胺基,所组成之群组;
R4表示具有5至30个环碳原子的经取代或未经取代芳基、具有5至30个碳原子的经取代或未经取代杂芳基、具有5至30个环碳原子的经取代或未经取代芳胺基、或5至30个环碳原子的经取代或未经取代杂芳胺基,所组成之群组;并且
R5至R8独立表示氢原子或取代物选自于由卤素、具有1至30个碳原子的经取代或未经取代烷基、具有6至30个碳原子的经取代或未经取代芳基、具有6至30个碳原子的经取代或未经取代芳烷基、和3至30个碳原子的经取代或未经取代杂芳基,所组成之群组。
在某些实施例中,本发明有机化合物是由下式(4)至式(21)其中之一表示:
在某些实施例中,上述烷基、芳烷基、芳基、或杂芳基是被一卤素、一烷基、一芳基、或一杂芳基取代。
在一些实施例中,R1至R4独立表示取代或未经取代的苯基、取代或未经取代的联苯基、取代或未经取代的芴基、取代或未经取代的苯并芴基、取代或未经取代的萘基、取代或未经取代的蒽基、取代或未经取代的菲基、取代或未经取代的芘基、取代或未经取代的烯基、取代或未经取代的三亚苯基、取代或未经取代的苯并咪唑基、取代或未经取代的咔唑基、取代或未经取代的双咔唑基、取代或未经取代的二苯并呋喃基、取代或未经取代的二苯并噻吩基、取代或未经取代的二苯基氧化膦基、取代或未经取代的三嗪基、取代或未经取代的二嗪基、取代或未经取代的吡啶基、取代或未经取代的菲咯啉基团、取代或未经取代的二氢吖啶基、取代或未经取代的吩噻嗪基、取代或未经取代的吩恶嗪基、取代或未经取代的二氢吩嗪基、取代或未经取代的二苯胺基、取代或未经取代的三苯胺基、取代或未经取代的苯基二苯并呋喃基胺基、取代或未经取代的苯基二苯并硫代苯胺基。
在一些实施例中,R1至R4独立为由以下取代物其中之一所表示:
较佳地,该有机化合物为以下化合物之一:
在本发明的另一个实施例中,提供了一种有有机电激发光组件。该有机电激发光组件(有机EL组件)包含由阴极和阳极组成的电极对、和在该电极对之间的发光层和一个或多个有机薄膜层。该发光层和该有机薄膜层中的至少一个包含式(1)的有机化合物。本发明使用式(1)的有机化合物作为发光层的材料(掺杂剂或主体),可使有机EL组件在相同电压(例如6V)下具有更高的亮度(例如998~1584cd/m2)或电流效率(例如5.13~8.21cd/A)、或更长的半衰期(例如314~492小时)。本发明的有机EL组件使用式(1)的有机化合物作为电子传输材料,可具有降低的驱动电压(例如约4.5~5.8V)、更低的功耗、更高的电流效率(例如约7.43~8.61cd/A)、更长的半衰期(例如约415~490小时)。
在一些实施例中,包含式(1)或的有机化合物的发光层为主体材料。所述主体材料可以是磷光主体材料或荧光主体材料。在某些实施例中,包含式(1)的有机化合物的发光层被用作荧光掺杂剂材料。
在一些实施例中,包含式(1)的有机化合物的有机薄膜层为电子传输层。
在本发明的另一实施例中,所述有机电激发光组件为一发光面板。在本发明的其他实施例中,所述有机电激发光组件为背光面板。
将借助以下的示例性实施例来清楚阐明本发明的有机化合物的详细制备,但本发明并不限于此等示例性实施例。实施例1至实施例8说明本发明的有机化合物的制备,而实施例9至实施例11说明有机EL组件的制造和测试报告。
实施例1
化合物C41的合成
中间体A1的合成
3克(12.1毫莫耳)的2-苯基萘-1-基硼酸、4.2克(12.1毫莫耳)的2,7-二溴-9,9-二甲基-9H-芴、0.28克(0.24毫莫耳)的混合物将四(三苯基膦)钯(Pd(PPh3)4)、10毫升2莫耳浓度的碳酸钠(Na2CO3水溶液),10毫升乙醇(EtOH)和30毫升甲苯(Toluene),的混合物除气并置于氮气下,然后在100℃加热6小时。反应完成后,将混合物冷却至室温。随后,用乙酸乙酯和水萃取有机层,然后用无水硫酸镁干燥。除去溶剂后,剩余物通过硅胶管柱层析纯化,得到中间体A1(3.6克,63.1%)。
中间体A2的合成
在已除气并充满氮气的500毫升三颈烧瓶中,将5.0克(10.5毫莫耳)的中间体A1溶解在300毫升无水二氯甲烷(CH2Cl2)中,然后将17克(105毫莫耳)的氯化铁(FeCl3)向其中加入。搅拌1小时后,向其中加入500毫升的硝基正丁烷(CH3NO2),然后分离有机层并真空除去溶剂。剩余物通过硅胶管柱层析纯化(己烷-二氯甲烷),得到白色固体A2(2.0克,40%)。
中间体A3的合成
将2克(3.8毫莫耳)的中间体A2、1.6克(6.3毫莫耳)的4,4,4',4',5,5,5',5'-八甲基-2,2'-双(1,3,2-二氧杂戊环烷)、0.09克(0.077毫莫耳)的四(三苯基膦)钯、1.2克(15.2毫莫耳)的乙酸钠(Na(OAc))、和60毫升1,4-二恶烷(1,4-Dioxane),的混合物除气并置于氮气下,然后在100℃加热6小时。反应完成后,将混合物冷却至室温。
随后,用乙酸乙酯和水萃取有机层,然后用无水硫酸镁干燥。除去溶剂后,将剩余物通过二氧化硅管柱层析纯化,得到中间体A3(1.7克,80%)。
化合物C41的合成
将2克(3.8毫莫耳)的中间体A3、1.1克(7.6毫莫耳)的2-氯-4,6-二苯基-1,3,5-三嗪、0.08克(0.07毫莫耳)的四(三苯基膦)钯、4毫升的2M碳酸钠(水溶液),10毫升的乙醇、和30毫升的甲苯,的混合物除气并置于氮气下,然后在100℃加热12小时。反应完成后,将混合物冷却至室温。随后,用二氯甲烷和水萃取有机层,然后用无水硫酸镁干燥。除去溶剂后,将剩余物通过二氧化硅管柱层析纯化,得到化合物C41(2.2克,53%)。MS(m/z,EI+):1172.75。
实施例2
化合物C18的合成
将2.0克(4.2毫莫耳)的中间体A2、1.2克(4.6毫莫耳)的5-苯基-5,10-二氢吩嗪,0.07克(0.08毫莫耳)的三(二亚苄基丙酮)二钯(Pd2(dba)3)、0.04克(0.21毫莫耳)三叔丁基膦(P(tBu)3)、1.2克(12.6毫莫耳)叔丁醇钠(NaOtBu)、和30毫升甲苯,的混合物除气并置于氮气下,然后在110℃下加热16小时。反应完成后,将混合物冷却至室温。随后,用二氯甲烷和水萃取有机层,然后用无水硫酸镁干燥。除去溶剂后,剩余物通过二氧化硅管柱层析纯化,得到化合物C18(2.6克,72%)。MS(m/z,EI+):866.25。
实施例3
化合物C37的合成中间体A4的合成
使用与合成中间体A1中相同的合成步骤,只是使用3.0克的2-(萘-2-基)苯基硼酸,代替2-苯基萘-1-基硼酸,并且使用3.9克2,8-二溴二苯并[b,d]呋喃,代替2,7-二溴-9,9-二甲基-9H-芴,以获得所需的中间体A4(3.3克,产率=61%)。
中间体A5的合成
使用与合成中间体A2中相同的合成步骤,只是使用3.0克中间体A4代替中间体A1,以获得所需的中间体A5(1.7克,产率=58.2%)。
中间体A6的合成
使用与合成中间体A3中相同的合成步骤,只是使用3克中间体A5代替中间体A2,以获得所需的中间体A6(2.4克,产率=74%)。
化合物C37的合成
使用与化合物C41合成中相同的合成步骤,只是使用3克的中间体A6代替中间体A3,并且使用1.4克的2-氯-1,10-邻二氮菲代替2-氯-4,6-二苯基-1,3,5-三嗪,以得到所需化合物C37(4.7克,产率=79.3%)。MS(m/z,EI+):990.16。
实施例4
化合物C43的合成
使用与化合物C41的合成中相同的合成步骤,只是使用3克中间体A6代替A3,并且使用2.0克9-溴-10-苯基蒽代替2-氯-4,6-二苯基-1,3,5-三嗪,以得到所需的化合物C43(5.2克,产率=76.3%)。
实施例5
化合物C54的合成中间体A7的合成
使用与合成中间体A1中相同的合成步骤,只是以3.0克的2-(4-甲氧基萘-2-基)苯基硼酸,代替2-苯基萘-1-基硼酸,并以2.6克的2-溴二苯并[b,d]呋喃,代替2,7-二溴-9,9-二甲基-9H-芴,而获得所需的中间体A7(3.8克,产率=88.5%)。
中间体A8的合成
使用与合成中间体A2中相同的合成步骤,只是以3.0克的中间体A7,代替中间体A1,而获得所需的中间体A8(1.7克,产率=56.2%)。
中间体A9的合成
将5克(12.5毫莫耳)的中间体A8和60毫升的二氯甲烷(DCM)的混合物在氮气下置于反应器中。向其中加入1当量的三溴化硼(BBr3),然后搅拌2小时直到反应完成。反应混合物用二氯甲烷和水萃取,然后用无水硫酸镁干燥。除去溶剂,得到中间体A9(3.9克,产率=81.4%)。
中间体A10的合成
将2.6克(6.76毫莫耳)的中间体A9,和60毫升的二氯甲烷(DCM)的混合物,在氮气下放置到反应器中。向其中加入1.5当量的吡啶(Pyridine)和1.7当量的三氟甲磺酸酐,然后搅拌12小时直至反应完成。反应混合物用二氯甲烷和水萃取,然后用无水硫酸镁干燥。除去溶剂,得到中间体A10(3.1克,产率=90%)。
中间体A11的合成
使用与合成中间体A3中相同的合成步骤,只是使用2.9克中间体A10代替中间体A2,以获得所需的中间体A11(2.0克,产率=73.6%)。
化合物C54的合成
使用与化合物C41的合成相同的合成步骤,只是使用3克中间体A11代替A3和2.1克2-(联苯基-4-基)-4-氯-6-苯基-使用1,3,5-三嗪代替2-氯-4,6-二苯基-1,3,5-三嗪,得到所需的化合物C54(5.6克,产率=69.8%)。
实施例6
化合物C25的合成
中间体A12的合成
使用与化合物C41的合成中相同的合成步骤,只是使用5克的2-(苯并[g]-3-基)-4,4,5,5-四甲基-1,3,2-二氧杂硼烷,代替中间体A3,并使用2.5克1-溴-2-硝基苯,代替2-氯-4,6-二苯基-1,3,5-三嗪,得到所需的中间体A12(3.6克,产率=74.1%)。
中间体A13的合成
将2克(5.0毫莫耳)的中间体A12、13.1克(50.0毫莫耳)的三苯膦、和30毫升的邻二氯苯(o-DCB)的混合物置于氮气下,然后在180℃下加热8小时。反应完成后,将混合物冷却至室温。将混合物倒入水中,然后过滤,得到中间体A13(0.9克,50%)。
化合物C25的合成
将3.0克(8.1毫莫耳)的中间体A13、3.1克(4.6毫莫耳)的2-(联苯-4-基)-4-氯-6-苯基-1,3,5-三嗪、0.15克(0.16毫莫耳)的Pd2(dba)3、0.03克(0.16毫莫耳)的三叔丁基膦,2.3克(24.3毫莫耳)的叔丁醇钠、和60毫升的甲苯,的混合物除气并置于氮气下,然后在110℃加热16小时。反应完成后,将混合物冷却至室温。随后,用二氯甲烷和水萃取有机层,然后用无水硫酸镁干燥。除去溶剂后,将剩余物通过硅胶上的管柱层析纯化,得到化合物C25(5.9克,74.1%)。MS(m/z,EI+):974.21。
实施例7
化合物C49的合成
3.0克(6.6毫莫耳)的中间体A5、1.6克(7.2毫莫耳)的N-苯基联苯-4-胺、0.12克(0.13毫莫耳)的三(二亚苄基丙酮)二钯(Pd2(dba)3)、0.03克(0.16毫莫耳)三叔丁基膦,2.0克(19.8毫莫耳)的叔丁醇钠、和60毫升甲苯,的混合物除气并置于氮气下,然后在110℃下加热16小时。反应完成后,将混合物冷却至室温。随后,用二氯甲烷和水萃取有机层,然后用无水硫酸镁干燥。除去溶剂后,将剩余物通过二氧化硅管柱层析纯化,得到化合物C49(6.6克,82.3%)。MS(m/z,EI+):1199.23。
实施例8
化合物C58的合成
使用与化合物C25的合成中相同的合成步骤,只是使用3克N-(3-溴苯基)-N-苯基二苯并[b,d]呋喃-4-胺,代替2-(联苯)-4-基)-4-氯-6-苯基-1,3,5-三嗪,以获得所需化合物C58(7.4克,产率=74.1%)。
生产有机电激发光组件的方法
提供阻值为9~12奥姆/平方(ohm/square)和厚度为120~160nm的铟锡氧化物涂层玻璃(以下称为ITO基板),并在超音波浴(例如洗涤剂、去离子水)中进行多步骤清洗。在气相沉积有机层之前,通过紫外光(UV)和臭氧进一步处理清洗过的ITO基板。ITO基板的所有前处理制程皆在洁净室(100级)内进行。
在高真空设备下(10-7Torr)利用电阻加热的石英舟以气相沉积将这些有机层依序涂布到ITO基板上。借助石英晶体监视器来精确监控或设定各层的厚度和气相沉积速率(0.1~0.3nm/sec)。如上所述,还可以使个别层包含多于一种化合物(即通常掺杂有掺杂材料的主体材料),此可通过来自两个或更多个来源的共气相沉积成功地实现,表示本发明的铱复合物具有热稳定性。
二吡嗪并[2,3-f:2,3-]喹喔啉-2,3,6,7,10,11-六氰基(Dipyrazino[2,3-f:2,3-]quinoxaline-2,3,6,7,10,11-hexacarbonitrile,HAT-CN)在有机EL装置中可用来作为电洞注入层,并且N,N-双(萘-1-基)-N,N-双(苯基)-联苯胺(NPB)用于形成有机EL组件的电洞传输层。2,9-双(萘-2-基)-4,7-二苯基-1,10-菲咯啉(NPhen),是有机EL组件中的电子传输材料,具有比浴铜灵(2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline,bathocuproine,BCP)或4,7-二苯基-1,10-邻二氮杂菲(BPhen)高的热稳定性和长的使用寿命。对于荧光发射组件,将1,1'-(9,9-二甲基-9H-芴-2,7-二基)二芘(DFDP)用作主体材料,而(E)-6-(4-(二苯基氨基)苯乙烯基)-N,N-二苯基萘-2-胺(D1)用作荧光掺杂剂。对于磷光发射组件,将双(2-甲基-8-喹啉酸酯)-4-(苯基苯酚基)铝(BAlq)用作发光层的主体材料,并使用三(1-苯基异喹啉)-铱(III)(Ir(piq)3)或三(2-苯基喹啉)铱(III)(Ir(2-phq)3)用作掺杂剂材料。使用化合物C9,C10,C11,C12,C13,C34,C43或C44作为荧光主体材料,与DFDP进行比较。使用化合物C5,C6,C7,C16,C19和C49作为荧光掺杂剂材料,与D1进行比较。化合物C15,C22,C23,C42和C45用作电子传输材料与NPhen进行比较。化合物C1,C2,C3,C4,C27,C39,C40和C58用作磷光主体材料,与BAlq进行比较。常规OLED材料,与本发明中用于生产对照和示例性有机EL组件的部分有机化合物的化学结构如下:
有机EL组件通常包含作为阴极的低功函数金属,例如Al、Mg、Ca、Li和K,且该低功函数金属可有助于电子从阴极注入电子传输层。另外,在阴极与电子传输层之间引入薄膜电子注入层,用于降低电子注入阻障并提高有机EL组件性能。电洞注入层材料为具有低功函数的金属卤化物或金属氧化物,例如:LiF、LiQ、MgO或Li2O。
另一方面,在制作有机EL组件之后,透过使用PR650光谱扫描光谱仪量测EL光谱和CIE坐标。此外,电流/电压、亮度/电压和效率/电压特性都使用吉时利(Keithley)2400可编程电压电流源来检测。在室温(约25℃)和大气压下操作上述设备。
实施例9
使用与上述方法类似的过程制作具有下列组件结构(如图1所示)的发荧光有机EL组件:ITO/HAT-CN(20nm)/NPB(50nm)/30nm荧光蓝色主体:(DFDP或C9、C10、C11、C12、C13、C34、C43或C44)+5%掺杂剂(D1或C5、C6、C7、C16、C19或C49)/NPhen(30nm)/LiF(0.5nm)/Al(160nm)。在图1所示的装置中,电洞注入层20沉积在透明电极10上,电洞传输层30沉积在电洞注入层20上,发射层40沉积在电洞传输层30上,电子传输层50沉积在发射层40上,电子注入层60沉积在电子传输层50上,金属电极70沉积在电子注入层60上。这些发蓝色荧光的有机EL组件的I-V-B和半衰期测试报告,总结在下表1中,并且半衰期定义为3000cd/m2的初始亮度降到一半的时间。
表1
从上述有机EL组件的测试报告总结,可以看出,用作蓝色荧光主体或掺杂剂材料的式(1)或式(2)的有机化合物,比现有技术的材料,具有更好的性能。特别地,使用式(1)或式(2)的有机化合物作为掺杂剂材料或主体材料,与主体材料DFDP或掺杂剂材料D1并置比较,可知本发明有机EL组件可以有改善的亮度或电流效率。在相同电压下,本发明有机EL组件可以有较长半衰期。
实施例10
使用类似于上述方法的程序,生产了具有以下组件结构的有机EL组件:ITO/HAT-CN(20nm)/NPB(50nm)/DFDP+5%D1(30nm)/NPhen或C15,C22,C23,C42或C45(30nm)/LiF(0.5nm)/Al(160nm)。这些发蓝色荧光的有机EL组件的I-V-B和半衰期测试报告总结在下表2中,并且半衰期定义为3000cd/m2的初始亮度降到一半的时间。
表2
电子传输层材料(ETM) | 电压(V) | 效率(cd/A) | CIE(y) | 半衰期(hrs) |
NPhen | 6.2 | 5.12 | 0.17 | 310 |
C15 | 4.5 | 8.61 | 0.17 | 483 |
C22 | 4.8 | 7.82 | 0.17 | 423 |
C23 | 4.7 | 7.43 | 0.17 | 410 |
C42 | 4.7 | 8.53 | 0.17 | 490 |
C45 | 4.6 | 8.32 | 0.17 | 488 |
从上述有机EL组件的测试报告总结,可以看出,用作电子传输材料的式(1)或式(2)的有机化合物,表现出比现有技术的材料NPhen更好的性能。特别地,使用式(1)或式(2)的有机化合物作为电子传输材料,与主体材料DFDP和掺杂剂材料D1搭配,所得的本发明有机EL组件具有较低的功耗、较高的电流效率、或较长长半衰期。
实施例11
使用类似于上述方法的程序,生产了具有以下组件结构的有机EL组件:ITO/HAT-CN(20nm)/NPB(50nm)/磷光主体(C1,C2,C3,C4,C27,C39,C40或C58)+10%掺杂剂(30nm)/NPhen(30nm)/LiF(0.5nm)/Al(160nm)。这些发磷光的有机EL组件的I-V-B和半衰期测试报告总结在下表3中,半衰期定义为3000cd/m2的初始亮度降到一半的时间。
表3
从上述有机EL组件的测试报告总结,可以看出,用作磷光主体材料的式(1)或式(2)的有机化合物,比现有技术的材料Balq,具有更好的性能。使用式(1)或式(2)的有机化合物作为磷光主体材料,并与掺杂剂材料Ir(piq)3或Ir(2-phq)3配位,所得的本发明的有机EL组件,具有较佳的亮度,并且在相同电压下,具有较佳的电流效率或较长的半衰期。
根据上述教示显然可以作出许多的修改和变化。因此,应当了解的是,在随附申请专利范围的范围内,可以以本文具体描述的方式以外的其他方式来实施本发明。虽然,本文中已说明并描述了具体实施例,但对于所属技术领域中具有通常知识者来说,显而易见的是可以在不偏离欲单独由随附申请专利范围限制的情况下对本发明作出许多修改。
Claims (10)
1.一种以下式(1)表示的有机化合物:
其中C1至C4或C5至C8四个碳原子里的两个连续碳原子,与下式(3)的结构稠合:
其中X是二价桥选自于由O、S、NR4、CR5R6、及SiR7R8组成的群组;
其中R4选自于由芳基、杂芳基、芳胺基、杂芳胺基、和其组合组成的群组;
其中R5至R8独立的选自于由烷基、芳基、芳烷基、杂芳基、和其组合组成的群组;
其中R9至R12独立地选自于由卤素、芳基、杂芳基、芳胺基、杂芳胺基、氘、烷基、环烷基、杂烷基、杂环烷基、芳烷基、烷氧基、芳氧基、氨基、硅烷基、烯基、环烯基、杂烯基、炔基、羰基、羧酸、醚、酯、二醇、异腈、硫基、亚磺酰胺、磺酰基、磷酸基、和其组合组成的群组;并且
其中每个R1至R3、和R9至R12独立表示氢、不存在、或取代物独立地选自于由卤素、芳基、杂芳基、芳胺基、杂芳胺基、氘、烷基、环烷基、杂烷基、杂环烷基、芳烷基、烷氧基、芳氧基、氨基、硅烷基、烯基、环烯基、杂烯基、炔基、羰基、羧酸、醚、酯、二醇、异腈、硫基、亚磺酰胺、磺酰基、磷酸基、和其组合组成的群组,且其中每个R1至R3表示的取代物在其附接的环碳原子上是单取代到可能的最大数目个取代;
其中R9与R10可接合在一起,或R11与R12可接合在一起,以形成苯环。
4.如权利要求1所述的有机化合物,其特征在于该烷基、芳烷基、芳基、或杂芳基是被一卤素、一烷基、一芳基、或一杂芳基取代。
5.如权利要求1所述的有机化合物,其特征在于R1至R4独立表示取代或未经取代的苯基、取代或未经取代的联苯基、取代或未经取代的芴基、取代或未经取代的苯并芴基、取代或未经取代的萘基、取代或未经取代的蒽基、取代或未经取代的菲基、取代或未经取代的芘基、取代或未经取代的烯基、取代或未经取代的三亚苯基、取代或未经取代的苯并咪唑基、取代或未经取代的咔唑基、取代或未经取代的双咔唑基、取代或未经取代的二苯并呋喃基、取代或未经取代的二苯并噻吩基、取代或未经取代的二苯基氧化膦基、取代或未经取代的三嗪基、取代或未经取代的二嗪基、取代或未经取代的吡啶基、取代或未经取代的菲咯啉基团、取代或未经取代的二氢吖啶基、取代或未经取代的吩噻嗪基、取代或未经取代的吩恶嗪基、取代或未经取代的二氢吩嗪基、取代或未经取代的二苯胺基、取代或未经取代的三苯胺基、取代或未经取代的苯基二苯并呋喃基胺基、和取代或未经取代的苯基二苯并硫代苯胺基。
8.一种有机电激发光组件,包含由阴极和阳极组成的一电极对、和在该电极对之间的一发光层和一个或更多个有机薄膜层,其特征在于,该发光层和该有机薄膜层中之至少一者包含如请求项1所述的有机化合物。
9.如权利要求8所述的有机电激发光组件,其特征在于,该发光层包含请求项1所述的有机化合物,以作为一主体材料或一荧光掺杂材料。
10.如权利要求8所述的有机电激发光组件,其特征在于包含请求项1的有机化合物的有机薄膜层是电子传输层。
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