CN113636943A - 三芳胺化合物及其在有机电致发光显示器件中的应用 - Google Patents
三芳胺化合物及其在有机电致发光显示器件中的应用 Download PDFInfo
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- CN113636943A CN113636943A CN202111002620.5A CN202111002620A CN113636943A CN 113636943 A CN113636943 A CN 113636943A CN 202111002620 A CN202111002620 A CN 202111002620A CN 113636943 A CN113636943 A CN 113636943A
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- carbon atoms
- triarylamine compound
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- organic electroluminescent
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- -1 Triarylamine compound Chemical class 0.000 title claims abstract description 43
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 32
- 239000000126 substance Substances 0.000 claims abstract description 21
- 125000005843 halogen group Chemical group 0.000 claims abstract description 15
- 230000005525 hole transport Effects 0.000 claims abstract description 15
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 14
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 14
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 14
- 125000003118 aryl group Chemical group 0.000 claims abstract description 13
- 239000000463 material Substances 0.000 claims abstract description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 7
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims abstract description 6
- 229910052805 deuterium Inorganic materials 0.000 claims abstract description 6
- 125000003709 fluoroalkyl group Chemical group 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000001769 aryl amino group Chemical group 0.000 claims description 2
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 2
- 125000005110 aryl thio group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000005462 imide group Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000002560 nitrile group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims description 2
- 229910052711 selenium Inorganic materials 0.000 claims description 2
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 21
- 125000005259 triarylamine group Chemical group 0.000 abstract description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 45
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- 230000015572 biosynthetic process Effects 0.000 description 20
- 239000007787 solid Substances 0.000 description 20
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- 239000012299 nitrogen atmosphere Substances 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
- 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 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 10
- 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 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
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- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 5
- WQONPSCCEXUXTQ-UHFFFAOYSA-N 1,2-dibromobenzene Chemical compound BrC1=CC=CC=C1Br WQONPSCCEXUXTQ-UHFFFAOYSA-N 0.000 description 5
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 239000012295 chemical reaction liquid Substances 0.000 description 5
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
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- 238000010791 quenching Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
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- 238000003756 stirring Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 125000000732 arylene group Chemical group 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000005549 heteroarylene group Chemical group 0.000 description 2
- 125000005945 imidazopyridyl group Chemical group 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 2
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 2
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000005493 quinolyl group Chemical group 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- WDBQJSCPCGTAFG-QHCPKHFHSA-N 4,4-difluoro-N-[(1S)-3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-pyridin-3-ylpropyl]cyclohexane-1-carboxamide Chemical compound FC1(CCC(CC1)C(=O)N[C@@H](CCN1CCC(CC1)N1C(=NN=C1C)C(C)C)C=1C=NC=CC=1)F WDBQJSCPCGTAFG-QHCPKHFHSA-N 0.000 description 1
- BWGRDBSNKQABCB-UHFFFAOYSA-N 4,4-difluoro-N-[3-[3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-thiophen-2-ylpropyl]cyclohexane-1-carboxamide Chemical compound CC(C)C1=NN=C(C)N1C1CC2CCC(C1)N2CCC(NC(=O)C1CCC(F)(F)CC1)C1=CC=CS1 BWGRDBSNKQABCB-UHFFFAOYSA-N 0.000 description 1
- VCOONNWIINSFBA-UHFFFAOYSA-N 4-methoxy-n-(4-methoxyphenyl)aniline Chemical compound C1=CC(OC)=CC=C1NC1=CC=C(OC)C=C1 VCOONNWIINSFBA-UHFFFAOYSA-N 0.000 description 1
- LFZAGIJXANFPFN-UHFFFAOYSA-N N-[3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-thiophen-2-ylpropyl]acetamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CCC(C=1SC=CC=1)NC(C)=O)C LFZAGIJXANFPFN-UHFFFAOYSA-N 0.000 description 1
- 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 1
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
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- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
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- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
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- 125000001624 naphthyl group Chemical group 0.000 description 1
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- 125000002971 oxazolyl group Chemical group 0.000 description 1
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Images
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- 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
- 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
- C07C211/54—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 two or three six-membered aromatic 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
- C07D209/94—[b, c]- or [b, d]-condensed containing carbocyclic rings other than six-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D345/00—Heterocyclic compounds containing rings having selenium or tellurium atoms as the only ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D421/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having selenium, tellurium, or halogen atoms as ring hetero atoms
- C07D421/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having selenium, tellurium, or halogen atoms as ring hetero atoms containing two hetero rings
- C07D421/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having selenium, tellurium, or halogen atoms as ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D421/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having selenium, tellurium, or halogen atoms as ring hetero atoms
- C07D421/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having selenium, tellurium, or halogen atoms as ring hetero atoms containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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Abstract
Description
技术领域
本发明属于有机电致发光材料领域,具体涉及三芳胺化合物及其在有机电致发光显示器件中的应用。
背景技术
目前,有机电致发光显示器件(OLED)的红光、绿光专用空穴传输层材料主要由芳香单胺组成,芳香单胺具有能级易调节的优势,可以根据器件对能级的不同要求进行设计,但单芳胺由于空穴传输功能位太少会导致迁移率较低。共轭稠环类化合物结构具有高迁移的特性,且稠环还可形成分子内位阻,如果在三芳胺的适当位置引入共轭稠环片段,不仅可以让三芳胺类化合物具有高迁移率,能级符合空穴传输材料的范围,而且有利于减少分子间的平面作用,提高玻璃转化温度从而提升器件寿命。基于此,本发明提出一种大位阻、高迁移率的三芳胺化合物,具体如下所述。
发明内容
本发明提供的三芳胺化合物,具有如化学式1所示的化学结构:
在化学式1中,X11–X14各自独立选自氢、氘、卤素原子、取代或未取代的碳原子数为1–20的烷基、烷氧基或烷硫基,X11–X14彼此相同或不同;
X15为取代或未取代的成环碳原子数为8–24且环数为4个的芳基、或者取代或未取代的成环碳原子数为8–24且环数为4个的杂芳基;
A2和A3各自独立为未取代的或卤素原子、氰基、碳原子数为1–10的烷基、烷氧基、烷硫基、氟烷基取代的成环碳原子数为5–24的芳基、或者未取代的或卤素原子、氰基、碳原子数为1–10的烷基、烷氧基、烷硫基、氟烷基取代的成环碳原子数为5–24的杂芳基。
与现有技术相比,本发明的有益效果在于:本发明中三芳胺化合物同时具有大位阻和高迁移率的优势,其中高迁移率可以有效提高分子间的结合力来降低结晶现象,大位阻可以让能级变深,符合R,G空穴传输材料的要求,可以提升OLED的发光效率和稳定性。
参考以下详细说明更易于理解本发明的上述以及其他特征、方面和优点。
附图说明
通过阅读参照以下附图对非限制性实施例所作的详细描述,本发明的其它特征、目的和优点将会变得更显著:
图1是实施例中底部发光有机电致发光显示器件的结构示意图。
图2是实施例中顶部发光有机电致发光显示器件的结构示意图。
具体实施方式
为使本发明实施例的目的、技术方案和优点更加清楚,下面将结合本发明实施例的附图,对本发明实施例的技术方案进行清楚、完整地描述。显然,所描述的实施例是本发明的一部分实施例,而不是全部的实施例。基于所描述的本发明的实施例,本领域普通技术人员在无需创造性劳动的前提下所获得的所有其它实施例,都属于本发明保护的范围。
本发明提供的三芳胺化合物,具有如化学式1所示的化学结构:
在化学式1中,X11–X14各自独立选自氢、氘、卤素原子、取代或未取代的碳原子数为1–20的烷基、烷氧基或烷硫基,X11–X14彼此相同或不同;
X15为取代或未取代的成环碳原子数为8–24且环数为4个的芳基、或者取代或未取代的成环碳原子数为8–24且环数为4个的杂芳基;
A2和A3各自独立为未取代的或卤素原子、氰基、碳原子数为1–10的烷基、烷氧基、烷硫基、氟烷基取代的成环碳原子数为5–24的芳基、或者未取代的或卤素原子、氰基、碳原子数为1–10的烷基、烷氧基、烷硫基、氟烷基取代的成环碳原子数为5–24的杂芳基。
根据一些实施方式,在化学式1中,X15选自以下任一个基团:
其中,X、X1和X2各自独立地选自O、S、Se、N-Me、N-Ph或C(Me)2,Y、Y1和Y2各自独立地选自O、S或Se。
根据一些实施方式,在化学式1中,A2和A3选自以下任一个基团:
其中,X、X1和X2各自独立地选自O、S、Se、N-Me、N-Ph或C(Me)2。
根据一些实施方式,在化学式1中,X11–X14各自独立选自氢、卤素原子、甲基、甲氧基、甲硫基、乙基、乙氧基、-CH2F、-CHF2或叔丁基,X11–X14彼此相同或不同。
化学式1中所示的三芳胺化合物中取代基的描述如下,当不限于此。
“取代或未取代的”指选自以下一个或多个取代基取代:氘、卤素基、腈基、硝基、羟基、羰基、酯基、酰亚胺基、氨基、氧化膦基、烷氧基、芳氧基、烷基硫基、芳基硫基、烷基磺酰基、芳基磺酰基、甲硅烷基、硼基、烷基、环烷基、烯基、芳基、芳烷基、芳烯基、烷基芳基、烷基胺基、芳烷基胺基、杂芳基胺基、芳基胺基和杂环基,或未取代;或者连接以上取代基中的两个或多个取代基的取代基取代,或未取代,如“连接两个或多个取代基的取代基”包括联苯基,即联苯基可为芳基或者为连接两个苯基的取代基。
“芳基”可为单环芳基或多环芳基,单环芳基包括苯基、联苯基、三联苯基、四联苯基、五联苯基,多环芳基包括萘基、蒽基、菲基、芘基、苝基、芴基,以上对芳基的描述可用于亚芳基,不同之处在于亚芳基为二价。
“杂环基”包括吡啶基、吡咯基、嘧啶基、哒嗪基、呋喃基、噻吩基、咪唑基、吡唑基、唑基、异唑基、噻唑基、异噻唑基、三唑基、二唑基、噻二唑基、二噻唑基、四唑基、吡喃基、噻喃基、吡嗪基、嗪基、噻嗪基、二氧杂环己烯基、三嗪基、四嗪基、喹啉基、异喹啉基、喹啉基、喹唑啉基、喹喔啉基、萘啶基、吖啶基、呫吨基、菲啶基、二氮杂萘基、三氮杂茚基、吲哚基、二氢吲哚基、中氮茚基、酞嗪基、吡啶并嘧啶基、吡啶并吡嗪基、吡嗪并吡嗪基、苯并噻唑基、苯并唑基、苯并咪唑基、苯并噻吩基、苯并呋喃基、二苯并噻吩基、二苯并呋喃基、咔唑基、苯并咔唑基、二苯并咔唑基、吲哚并咔唑基、茚并咔唑基、吩嗪基、咪唑并吡啶基、吩嗪基、菲啶基、菲咯啉基、吩噻嗪基、咪唑并吡啶基、咪唑并菲啶基、苯并咪唑并喹唑啉基、苯并咪唑并菲啶基;以上对杂环基的描述可用于杂芳基,不同之处在于杂芳基为芳香族,以上对杂环基的描述可用于亚杂芳基,不同之处在于亚杂芳基为二价。
根据一些实施方式,化学式1中所示的三芳胺化合物选自以下任一个化学结构:
以下合成实施例1至5详细描述了上述三芳胺化合物1、2、3、4和5的制备方法,未注明制备方法的原料均为市售商品,本发明中其他化合物的合成与合成实施例1至5类似。
合成实施例1
本合成实施例中合成三芳胺化合物1,技术路线如下所示:
化合物1-2的合成:氮气氛围下,向三口烧瓶中依次加入三(二亚苄基丙酮)二钯(1mol%,110mg,0.12mmol),三叔丁基膦(97mg,0.48mmol)和无水甲苯(90mL),室温下搅拌30分钟。随后依次加入双(4-甲氧基苯基)胺(化合物1-1)(2.75g,12mmol)、邻二溴苯(3.11g,13.2mmol)、叔丁醇钠(2.88g,30mmol),并将所得混合物在氮气氛围下回流搅拌18小时,冷却后将反应液倒入二氯甲烷中并用水洗涤,有机相用无水硫酸钠干燥,过滤并真空蒸发去除溶剂,粗产物依次通过硅胶柱色谱和乙醇、正己烷混合溶剂重结晶,得到白色固体3.7g,收率80%。
化合物1的合成:在氮气氛下,将化合物1-2(3.0g,7.8mmol)、1-3(3.3g,7.8mmol)、碳酸钾(138mg,1mmol)和60mL无水甲苯依次加入到三口瓶中,温度升至70℃,加入四(三苯基膦)钯(93mg,0.08mmol)和脱气去离子水30mL,充分搅拌后回流18小时,趁热将反应液经过硅藻土过滤,滤液在旋转蒸发仪上旋干,得到灰色固体粗品,用丙酮、甲苯和四氢呋喃混合溶剂重结晶得到固体然后升华,最终得到浅黄色固体2.4g,产率52%。
合成实施例2
本合成实施例中合成三芳胺化合物2,技术路线如下所示:
化合物2-2的合成:氮气氛围下,依次将三(二亚苄基丙酮)二钯(1mol%,110mg,0.12mmol),三叔丁基膦(97mg,0.48mmol)和无水甲苯(90mL)加入三口瓶中,并于室温下搅拌30分钟。随后依次加入化合物2-1(3.11g,12mmol)、邻二溴苯(3.11g,13.2mmol)、叔丁醇钠(2.88g,30mmol),在氮气氛围下回流搅拌18小时,冷却后将反应液倒入150mL蒸馏水中淬灭反应,并萃取,将有机相用无水硫酸钠干燥,过滤并真空蒸发去除溶剂,粗产物依次通过硅胶柱色谱和乙醇、正己烷混合溶剂重结晶,得到白色固体3.6g,收率72%。
化合物2的合成:在氮气氛下,将化合物2-2(3.0g,7.8mmol)、2-3(3.8g,7.8mmol)、碳酸钾(138mg,1mmol)和60mL无水甲苯依次加入到三口瓶中,温度升至70℃,加入四(三苯基膦)钯(93mg,0.08mmol)和脱气去离子水30mL,充分搅拌后回流18小时,趁热将反应液经过硅藻土过滤,滤液在旋转蒸发仪上旋干,得到灰色固体粗品,用丙酮、甲苯和四氢呋喃混合溶剂重结晶得到固体然后升华,最终得到浅黄色固体2.5g,产率46%。
合成实施例3
本合成实施例中合成三芳胺化合物3,技术路线如下所示:
化合物3-2的合成:氮气氛围下,依次将三(二亚苄基丙酮)二钯(1mol%,110mg,0.12mmol),三叔丁基膦(97mg,0.48mmol)和无水甲苯(90mL)加入三口瓶中,并于室温下搅拌30分钟。随后依次加入化合物3-1(3.87g,12mmol)、邻二溴苯(3.11g,13.2mmol)、叔丁醇钠(2.88g,30mmol),在氮气氛围下回流搅拌20小时,冷却后将反应液倒入150mL蒸馏水中淬灭反应,并萃取,将有机相用无水硫酸钠干燥,过滤并真空蒸发去除溶剂,粗产物依次通过硅胶柱色谱和乙醇、正己烷混合溶剂重结晶,得到白色固体4.0g,收率69%。
化合物3的合成:在氮气氛下,将化合物3-2(3.8g,8.0mmol)、3-3(3.9g,8.0mmol)、碳酸钾(138mg,1mmol)和60mL无水甲苯依次加入到三口瓶中,温度升至70℃,加入四(三苯基膦)钯(93mg,0.08mmol)和脱气去离子水30mL,充分搅拌后回流18小时,趁热将反应液经过硅藻土过滤,滤液在旋转蒸发仪上旋干,得到灰色固体粗品,用丙酮、甲苯和四氢呋喃混合溶剂重结晶得到固体然后升华,最终得到浅黄色固体2.7g,产率45%。
合成实施例4
本合成实施例中合成三芳胺化合物4,技术路线如下所示:
化合物4-2的合成:氮气氛围下,依次将三(二亚苄基丙酮)二钯(1mol%,110mg,0.12mmol),三叔丁基膦(97mg,0.48mmol)和无水甲苯(90mL)加入三口瓶中,并于室温下搅拌30分钟。随后依次加入化合物4-1(4.58g,12mmol)、邻二溴苯(3.11g,13.2mmol)、叔丁醇钠(2.88g,30mmol),在氮气氛围下回流搅拌16小时,冷却后将反应液倒入150mL蒸馏水中淬灭反应,并萃取,将有机相用无水硫酸钠干燥,过滤并真空蒸发去除溶剂,粗产物依次通过硅胶柱色谱和乙醇、正己烷混合溶剂重结晶,得到白色固体4.8g,收率75%。
化合物4的合成:在氮气氛下,将化合物4-2(4.60g,8.57mmol)、3-3(3.33g,8.57mmol)、碳酸钾(138mg,1mmol)和60mL无水甲苯依次加入到三口瓶中。温度升至70℃,加入四(三苯基膦)钯(93mg,0.08mmol)和脱气去离子水30mL,充分搅拌后回流18小时,趁热将反应液经过硅藻土过滤,滤液在旋转蒸发仪上旋干,得到灰色固体粗品,用丙酮、甲苯和四氢呋喃混合溶剂重结晶得到固体然后升华,最终得到浅黄色固体3.0g,产率49%。。
合成实施例5
本合成实施例中合成三芳胺化合物5,技术路线如下所示:
化合物5-2的合成:氮气氛围下,依次将三(二亚苄基丙酮)二钯(1mol%,110mg,0.12mmol),三叔丁基膦(97mg,0.48mmol)和无水甲苯(90mL)加入三口瓶中,并于室温下搅拌30分钟。随后依次加入化合物4-1(4.03g,12mmol)、邻二溴苯(3.11g,13.2mmol)、叔丁醇钠(2.88g,30mmol),在氮气氛围下回流搅拌20小时,冷却后将反应液倒入150mL蒸馏水中淬灭反应,并萃取,将有机相用无水硫酸钠干燥,过滤并真空蒸发去除溶剂,粗产物依次通过硅胶柱色谱和乙醇、正己烷混合溶剂重结晶,得到白色固体4.0g,收率68%。
化合物5的合成:在氮气氛下,将化合物5-2(3.90g,7.95mmol)、3-3(2.91g,7.95mmol)、碳酸钾(138mg,1mmol)和60mL无水甲苯依次加入到三口瓶中,温度升至70℃,加入四(三苯基膦)钯(93mg,0.08mmol)和脱气去离子水30mL,充分搅拌后回流19小时,趁热将反应液经过硅藻土过滤,滤液在旋转蒸发仪上旋干,得到灰色固体粗品,用丙酮、甲苯和四氢呋喃混合溶剂重结晶得到固体然后升华,最终得到浅黄色固体2.5g,产率46%。
本发明还提供上述三芳胺化合物在有机电致发光显示器件中的应用,具体是该化合物作为有机电致发光显示器件中空穴传输层的材料。以下器件实施例制备的有机电致发光显示器件,包括第一电极、第二电极、以及设置在第一电极和第二电极之间的一个或多个有机材料层,可为底部发射型、顶部发射型或双发射型,其有机材料层可为单层结构,也可为层合有两个或多个有机材料层的多层结构,如具有包括空穴注入层、空穴传输层、发光层、电子传输层、电子注入层等作为有机材料层的结构,可使用制备有机电致发光显示器件的常见方法和材料来制备。本发明的上述三芳胺化合物可以在红光、绿光、蓝光等各种光色中使用,也可以采用如图1和2所示的底部发光器件和顶部发光器件结构。器件实施例1至5制备单色底部发光器件,分别将上述三芳胺化合物1、2、3、4和5用作空穴传输层材料。
器件实施例1
按照如图1所示的结构制作红光底部发光的有机电致发光显示器件,制备工艺为:在玻璃材质的基底101上,形成透明阳极ITO膜层,膜层厚度为150nm,得到第一电极102作为阳极,之后蒸镀与化合物的混合材料作为空穴注入层103,混合比例为3:97(质量比),之后蒸镀厚度为100nm的化合物得到第一层空穴传输层104,然后蒸镀本发明中厚度为100nm的化合物1,得到第二层空穴传输层105,以97:3的蒸镀速率蒸镀与40nm,制作红光发光单元106,蒸镀厚度为10nm的形成电子阻挡层107,与混合比例为4:6(质量比)形成厚度为30nm的电子传输层108,之后形成厚度为100nm的镁银(质量比1:9),作为第二电极109。
器件实施例2至5中分别采用上述三芳胺化合物2、3、4和5替代器件实施例1中三芳胺化合物1作为空穴传输层105来制作红光底部发光的有机电致发光显示器件,对比例1至4中分别采用化合物 替代器件实施例1中化合物1作为空穴传输层105来制作红光底部发光的有机电致发光显示器件,得到的有机电致发光显示器件进行发光效率性能测试,如表1所示。
表1
从表1可以看出,采用本发明中三芳胺化合物作为红光有机电致发光显示器件的空穴传输层105材料,得到的器件发光效率高、驱动电压低且使用寿命长。需要说明的是,有的器件构造如采用图2所示的顶部发光结构,尽管与上述器件结构不同,但仍然在空穴相关传输中有效,且本发明的上述化合物也可以在空穴传输层104中使用,同样效果显著。
另外,本发明还提供一种包含上述任一有机电致发光显示器件的显示装置。
Claims (10)
4.根据权利要求1所述的三芳胺化合物,其特征在于,当所述取代未说明时,所述取代选自以下一个或多个取代基取代:氘、卤素基、腈基、硝基、羟基、羰基、酯基、酰亚胺基、氨基、氧化膦基、烷氧基、芳氧基、烷基硫基、芳基硫基、烷基磺酰基、芳基磺酰基、甲硅烷基、硼基、烷基、环烷基、烯基、芳基、芳烷基、芳烯基、烷基芳基、烷基胺基、芳烷基胺基、杂芳基胺基、芳基胺基和杂环基;或者连接以上取代基中的两个或多个取代基的取代基取代。
5.根据权利要求1所述的三芳胺化合物,其特征在于,在化学式1中,X11–X14各自独立选自氢、卤素原子、甲基、甲氧基、甲硫基、乙基、乙氧基、-CH2F、-CHF2或叔丁基。
7.权利要求1至6任一项所述的三芳胺化合物在有机电致发光显示器件中的应用。
8.一种有机电致发光显示器件,包含上述权利要求1至6任一项所述三芳胺化合物。
9.根据权利要求8所述的有机电致发光显示器件,其特征在于,所述三芳胺化合物作为机电致发光显示器件的空穴传输层材料。
10.一种显示装置,其特征在于,包含权利要求8或9所述的有机电致发光显示器件。
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