CN114702395A - 三芳胺化合物和包含该化合物的有机电致发光器件 - Google Patents
三芳胺化合物和包含该化合物的有机电致发光器件 Download PDFInfo
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- CN114702395A CN114702395A CN202210409935.XA CN202210409935A CN114702395A CN 114702395 A CN114702395 A CN 114702395A CN 202210409935 A CN202210409935 A CN 202210409935A CN 114702395 A CN114702395 A CN 114702395A
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- -1 Triarylamine compound Chemical class 0.000 title claims abstract description 59
- 150000001875 compounds Chemical class 0.000 claims abstract description 122
- 230000005525 hole transport Effects 0.000 claims abstract description 33
- 239000000463 material Substances 0.000 claims abstract description 21
- 125000003118 aryl group Chemical group 0.000 claims abstract description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 12
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- 125000005549 heteroarylene group Chemical group 0.000 claims abstract description 3
- 125000001424 substituent group Chemical group 0.000 claims description 20
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 16
- 229910052805 deuterium Inorganic materials 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 10
- 125000005259 triarylamine group Chemical group 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 150000002894 organic compounds Chemical class 0.000 claims description 8
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 6
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 6
- 125000006716 (C1-C6) heteroalkyl group Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 239000000758 substrate Substances 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 2
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 2
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 2
- 125000005567 fluorenylene group Chemical group 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004957 naphthylene group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 239000010410 layer Substances 0.000 claims 3
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000005878 benzonaphthofuranyl group Chemical group 0.000 claims 1
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 238000005286 illumination Methods 0.000 claims 1
- WDYHPKURZUGMIN-UHFFFAOYSA-N n-[4-chloro-3-(pyridin-3-yloxymethyl)phenyl]-3-fluoro-5-morpholin-4-ylbenzamide Chemical compound C=1C(F)=CC(N2CCOCC2)=CC=1C(=O)NC(C=1)=CC=C(Cl)C=1COC1=CC=CN=C1 WDYHPKURZUGMIN-UHFFFAOYSA-N 0.000 claims 1
- 230000005693 optoelectronics Effects 0.000 claims 1
- 239000012044 organic layer Substances 0.000 claims 1
- 238000013086 organic photovoltaic Methods 0.000 claims 1
- 239000007858 starting material Substances 0.000 description 31
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
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- 230000000052 comparative effect Effects 0.000 description 22
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 15
- 238000002347 injection Methods 0.000 description 11
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
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- GMMUCVGZXGOUNM-UHFFFAOYSA-N (2-bromo-4-chlorophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Cl)C=C1Br GMMUCVGZXGOUNM-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 239000011777 magnesium Substances 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
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000001819 mass spectrum Methods 0.000 description 5
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- BZBCKUJXBABAQD-UHFFFAOYSA-N 2-iodo-1,4-dioxane Chemical compound IC1COCCO1 BZBCKUJXBABAQD-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
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- 238000010898 silica gel chromatography Methods 0.000 description 4
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- 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 4
- DKYRKAIKWFHQHM-UHFFFAOYSA-N (3,5-dichlorophenyl)boronic acid Chemical compound OB(O)C1=CC(Cl)=CC(Cl)=C1 DKYRKAIKWFHQHM-UHFFFAOYSA-N 0.000 description 3
- HVPHTYHDVLGKMO-UHFFFAOYSA-N (4-bromo-2-chlorophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Br)C=C1Cl HVPHTYHDVLGKMO-UHFFFAOYSA-N 0.000 description 3
- NLOOVMVNNNYLFS-UHFFFAOYSA-N 6-bromo-1,1,4,4-tetramethyl-2,3-dihydronaphthalene Chemical compound BrC1=CC=C2C(C)(C)CCC(C)(C)C2=C1 NLOOVMVNNNYLFS-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 238000006069 Suzuki reaction reaction Methods 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- 125000005619 boric acid group Chemical group 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 229940125898 compound 5 Drugs 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
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- 238000001514 detection method Methods 0.000 description 3
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- 229910052749 magnesium Inorganic materials 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
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- 238000006467 substitution reaction Methods 0.000 description 3
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- 238000004809 thin layer chromatography Methods 0.000 description 3
- VWCZANMQOQOJTE-UHFFFAOYSA-N (2,4-dibromophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Br)C=C1Br VWCZANMQOQOJTE-UHFFFAOYSA-N 0.000 description 2
- WQBLCGDZYFKINX-UHFFFAOYSA-N (3,5-dibromophenyl)boronic acid Chemical compound OB(O)C1=CC(Br)=CC(Br)=C1 WQBLCGDZYFKINX-UHFFFAOYSA-N 0.000 description 2
- FBOYMIDCHINJKC-UHFFFAOYSA-N 5-bromo-1,3-benzodioxole Chemical compound BrC1=CC=C2OCOC2=C1 FBOYMIDCHINJKC-UHFFFAOYSA-N 0.000 description 2
- MKXRBLPVLSQBDL-UHFFFAOYSA-N 5-iodo-1-methyl-2,3-dihydroindole Chemical compound IC1=CC=C2N(C)CCC2=C1 MKXRBLPVLSQBDL-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 125000005605 benzo group Chemical group 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- QNEGDGPAXKYZHZ-UHFFFAOYSA-N (2,4-dichlorophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Cl)C=C1Cl QNEGDGPAXKYZHZ-UHFFFAOYSA-N 0.000 description 1
- BMQDAIUNAGXSKR-UHFFFAOYSA-N (3-hydroxy-2,3-dimethylbutan-2-yl)oxyboronic acid Chemical group CC(C)(O)C(C)(C)OB(O)O BMQDAIUNAGXSKR-UHFFFAOYSA-N 0.000 description 1
- JAUCIDPGGHZXRP-UHFFFAOYSA-N 4-phenyl-n-(4-phenylphenyl)aniline Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1NC(C=C1)=CC=C1C1=CC=CC=C1 JAUCIDPGGHZXRP-UHFFFAOYSA-N 0.000 description 1
- BSLVNOLUEJOXMR-UHFFFAOYSA-N 5-iodo-2,3-dihydro-1-benzofuran Chemical compound IC1=CC=C2OCCC2=C1 BSLVNOLUEJOXMR-UHFFFAOYSA-N 0.000 description 1
- ZHQNDEHZACHHTA-UHFFFAOYSA-N 9,9-dimethylfluorene Chemical compound C1=CC=C2C(C)(C)C3=CC=CC=C3C2=C1 ZHQNDEHZACHHTA-UHFFFAOYSA-N 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 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
- 150000001412 amines Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- MXQOYLRVSVOCQT-UHFFFAOYSA-N palladium;tritert-butylphosphane Chemical compound [Pd].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C MXQOYLRVSVOCQT-UHFFFAOYSA-N 0.000 description 1
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
- 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
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C07D217/04—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D267/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D267/02—Seven-membered rings
- C07D267/08—Seven-membered rings having the hetero atoms in positions 1 and 4
- C07D267/12—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D267/14—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems condensed with one six-membered ring
-
- 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
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D307/81—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- 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
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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Abstract
本发明公开了三芳胺化合物和包含该化合物的有机电致发光器件,该化合物具有式(1)所示的结构,L1和L2选自单键、取代或未取代的亚苯基,L11、L12、L21和L22选自单键、取代或未取代的C6‑C30亚芳基、取代或未取代的C3‑C30亚杂芳基;Ar11、Ar12、Ar21和Ar22选自取代或未取代的C6‑C30芳基、取代或未取代的C3‑C30杂芳基;基团A选自如2‑a、2‑b或2‑c所示基团。本发明的化合物作为空穴传输材料用于有机电致发光器件可以保证器件具有较高的空穴迁移率,同时能有效阻挡电子、激子进入到空穴传输层中,大大提高器件的发光效率和使用寿命。
Description
技术领域
本发明属于有机发光材料领域,具体涉及三芳胺化合物和包含该化合物的有机电致发光器件。
背景技术
有机电致发光器件(OLED)具有亮度高、功耗低、质量轻、厚度薄、响应速度快、对比度高、可视角宽等优势,正受到学术界和产业界的广泛关注。目前常见的有机电致发光器件主要由电极、载流子传输层和发光层三部分构成,其中空穴传输层材料负责将阳极处的空穴传递至发光层,占据十分重要的地位。目前主要采用芳香胺化合物,这类分子具有良好的空穴传输特性,且前线轨道能级易于调节。例如,专利申请CN113816863A公开了三芳胺类化合物,以三芳胺为中心,在芴基的苯或9-位苯基上并有脂肪环,脂肪环相对于芳基具有更好的给电子能力,使得化合物具有良好的空穴传输性能以及热稳定性,同时能够为有机电致发光器件提供良好的使用寿命。专利申请CN113620818A公开了含稠环的三芳胺类化合物,以三芳胺为中心,同时连接苯并脂肪环和稠芳基基团,脂肪环相对于芳基具有推电子能力,使得化合物具有优异的空穴传输性能,稠芳基增加化合物的分子量,提高化合物的玻璃化转化温度,稳定性较好,是良好的空穴传输材料。专利申请CN113773207A通过将苯并五元/六元环结合到三芳胺中使得分子的空间构型更立体,提高空穴传输层与发光层之间的匹配性,并且有利于三线态能级(T1)的提高,从而有效地阻挡激子扩散,提高器件的效率。
目前,有机发光材料的研究已经在学术界和工业界广泛开展,大量性能优良的有机发光材料陆续被开发出来。总体来看,未来有机发光器件的方向是发展高效率、长寿命、低成本的白光器件和全彩色显示器件,但该技术的产业化进程仍面临许多关键问题。因此,设计与寻找一种稳定高效的有机化合物作为有机发光器件材料以克服其在实际应用过程中出现的不足,是有机发光器件研究中的重点与今后的研发趋势。
发明内容
本发明提供了一种三芳胺化合物,该化合物具有如式(1)所示的结构:
在式(1)中,L1和L2相同或不相同,各自独立地选自单键、取代或未取代的亚苯基;
L11、L12、L21和L22相同或不相同,各自独立地选自单键、取代或未取代的C6-C30亚芳基、取代或未取代的C3-C30亚杂芳基;
Ar11、Ar12、Ar21和Ar22相同或不相同,各自独立地选自取代或未取代的C6-C30芳基、取代或未取代的C3-C30杂芳基;
基团A选自如2-a、2-b或2-c所示基团中的一种:
在式2-a至2-c中,Z1、Z2、Z3、Z4和Z5各自独立地选自-CR1R2-、-NR-、O或S;
R选自取代或未取代的C1-C6烷基、取代或未取代的C1-C6杂烷基、取代或未取代的C3-C12环烷基、取代或未取代的C2-C12杂环烷基、取代或未取代的C6-C12芳基;
RA选自氢、氘、卤素、氰基、取代或未取代的C1-C12烷基、取代或未取代的C1-C12烷氧基、取代或未取代的C1-C12烷硫基、取代或未取代的C3-C18环烷基、取代或未取代的C2-C18杂环烷基、取代或未取代的C6-C30芳基、取代或未取代的C2-C30杂芳基;
n选自0、1、2或3,*表示连接位点。
作为优选,式(1)选自如式1-a和1-b所示的通式结构:
在式1-a和1-b中,各取代基同式(1)所述。
作为优选,在式2-a至2-c中,Z1、Z2、Z3、Z4和Z5各自独立地选自-NR-、O或S且数量大于1时,满足任意两个选自-NR-、O或S的取代基之间间隔至少一个-CR1R2-。
作为优选,在式2-a中,当Z1和Z3均为O时,满足Z2为-CR1R2-且至少一个R1和R2为氘代或未取代的甲基。
作为优选,在式2-b中,当Z1、Z2、Z3和Z4均为-CR1R2-时,满足至少一个R1和R2为氘代或未取代的甲基。
作为优选,在式(1)中,“取代或未取代的”的“取代的”表示被独立地选自由氘、卤素、氰基、硝基、C1-C12烷基、C3-C18环烷基、C1-C12烷氧基、C1-C12烷硫基、C6-C30芳基、C2-C30杂芳基中的一个或多个取代基所取代,且L1、L2、L11、L12、L21、L22、Ar11、Ar12、Ar21和Ar22中的取代基彼此相同或不相同。
作为优选,在式(1)中,基团A选自如下取代基团中的一种:
其中,R选自取代或未取代的C1-C6烷基、取代或未取代的C1-C6杂烷基、取代或未取代的C3-C12环烷基、取代或未取代的C2-C12杂环烷基、取代或未取代的C6-C12芳基;
RA选自氢、氘、卤素、氰基、取代或未取代的C1-C12烷基、取代或未取代的C1-C12烷氧基、取代或未取代的C1-C12烷硫基、取代或未取代的C3-C18环烷基、取代或未取代的C2-C18杂环烷基、取代或未取代的C6-C30芳基、取代或未取代的C2-C30杂芳基;
n选自0、1、2或3,*表示连接位点。
作为优选,在式(1)中,L1和L2相同或不相同,各自独立地选自单键、取代或未取代的亚苯基,其中“取代或未取代的”的“取代的”表示被独立地选自氘、甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、甲氧基、乙氧基、甲硫基、乙硫基、环丁基、环戊基、环己基中的一个或多个取代基所取代,且L1、L2的取代基数量和种类相同或不相同。
作为优选,在式(1)中,L11、L12、L21和L22相同或不相同,各自独立地选自单键、取代或未取代的亚苯基、取代或未取代的亚萘基、取代或未取代的亚联苯基、取代或未取代的亚芴基、取代或未取代基的亚二苯并噻吩基、取代或未取代基的亚二苯并呋喃基,其中“取代或未取代的”的“取代的”表示被独立地选自选自氘、氟、氰基、甲基、乙基、正丙基、异丙基、叔丁基、甲氧基、乙氧基、甲硫基、乙硫基、环丁基、环戊基、环己基、苯基、萘基、联苯基、二苯并呋喃基、二苯并噻吩基、咔唑基中的一个或多个取代基所取代,且L11、L12、L21和L22的取代基数量和种类相同或不相同。
作为优选,在式(1)中,Ar21和Ar22相同或不相同,各自独立地选自取代或未取代的苯基、取代或未取代的萘基、取代或未取代的噻吩基、取代或未取代的呋喃基、取代或未取代的硒吩基、取代或未取代的苯并噻吩基、取代或未取代的苯并呋喃基、取代或未取代的苯并硒吩基、取代或未取代的二苯并噻吩基、取代或未取代的二苯并呋喃基、取代或未取代的二苯并硒吩基、取代或未取代的芴基、取代或未取代的硅芴基、取代或未取代的咔唑基、取代或未取代的苯并萘并噻吩基、取代或未取代的苯并萘并呋喃基、取代或未取代的苯并萘并硒吩基、取代或未取代的苯并芴基、取代或未取代的苯并咔唑基,且其中“取代或未取代的”的“取代的”表示被独立地选自氘、氟、氰基、三甲基硅基、三氟甲基、C1-C6烷基、C4-C6环烷基、C1-C6烷氧基、C1-C6烷硫基、C6-C14芳基、C5-C14杂芳基中的一个或多个取代基所取代,且Ar11、Ar12、Ar21和Ar22的取代基数量和种类相同或不相同。
作为优选,式(1)所示的化合物选自以下任一个化学结构:
本发明还提供一种有机光电材料,其包含上述任意所述三芳胺化合物,可以作为有机电致发光器件的空穴传输层材料。
本发明还提供一种有机电致发光器件,其包含上述任意所述三芳胺化合物或者所述有机光电材料。
本发明还提供一种显示或照明装置,其包括所述的有机电致发光器件。
与现有技术相比,本发明的三芳胺化合物中分子的非对称结构不容易结晶,玻璃化转变温度通常较高,有利于提升器件寿命,同时氮上连接不同芳香基团,分子能级易于调节,可以满足红、绿光器件空穴传输材料的性能要求。将这类化合物作为空穴传输材料应用于有机电致发光器件,能够提高发光效率、器件寿命以及降低器件的驱动电压,可应用于各类显示或照明装置。此外,本发明的三芳胺化合物有机合成方法简单,易于产业化生产。
附图说明
图1是实施例中底部发光有机电致发光器件的结构示意图。
图2是实施例中顶部发光有机电致发光器件的结构示意图。
附图标记如下:101、基底层;102-第一电极(阳极);103、空穴注入层;104、第一层空穴传输层;105、第二层空穴传输层;106、有机发光层;107、空穴阻挡层;;108、电子传输层;109、第二电极(阴极);110、覆盖层。
具体实施方式
本发明提供的式(1)所示的三芳胺化合物可通过本领域常规的偶联反应即可制备得到,例如通过如下合成路线制备得到:
在化合物i和ii中,W1和W0中一个为卤素原子I或Br,另一个为硼酸基或片哪醇硼酯基;X1和X2均为卤素原子,当Y1或Y0中的任意一个选为I时,X1和X2相同或不同地选为Br或Cl;当Y1或Y0中的任意一个选为Br时,X1和X2为Cl。
在化合物iii中,当L1不为单键时,Y1可选自硼酸基或片哪醇硼酯基;当L1为单键时,Y1为氢。
在化合物iv中,当L2不为单键时,Y2可选自硼酸基或片哪醇硼酯基;当L2为单键时,Y2为氢。
本发明提供的芳香胺化合物可通过本领域常规的铃木偶联反应和布赫瓦尔德偶联反应得到,即在惰性气体氛围下,首先,多取代苯类化合物i与包含苯并环烷或苯并杂环烷的衍生物ii通过铃木偶联反应得到中间体化合物MA;随后化合物MA通过两步偶联反应,依次与胺类化合物iii和iv反应,在相应的催化剂、有机碱、配体、溶液以及相应温度下反应,经中间体化合物MB最终得到目标化合物。其中,当胺类化合物iii或iv中的L1或L2为单键时,采用布赫瓦尔德偶联反应;当胺类化合物iii或iv中的L1或L2不为单键时,采用铃木偶联反应。
本发明中目标化合物I的合成路线、中间物质中反应基团不局限于此。采用本领域熟知的其他合成手段获得目标化合物,均应在本发明的保护范围内。下面结合合成实施例来具体说明本发明中三芳胺化合物的合成方法,本发明中未提及合成方法的化合物均通过商业途径获得。
(1)化合物HT-9的合成:
(1-1)中间体化合物MA-9的合成:
在氮气氛围下,向三口烧瓶中依次加入2,4-二氯苯硼酸(1.9g,10.0mmol,1eq),6-溴-1,1,4,4-四甲基-1,2,3,4-四氢化萘(3.0g,11.2mmol,1.1eq),碳酸钾(3.5g,25.3mmol,2.5eq),四(三苯基膦)钯(57.8mg,0.05mmol,0.5%eq),以及脱气的甲苯(50mL)、乙醇(30mL)和水(20mL)。上述混合体系在氮气氛围下回流反应13小时,冷却至室温后倒入80mL乙酸乙酯中,静置分层,用乙酸乙酯(3×80mL)萃取,合并所得有机相并用无水硫酸镁干燥,过滤并减压蒸馏除去溶剂。将所得粗产品用乙醇/正己烷的混合溶剂重结晶,得到化合物MA-9(2.6g,收率78.3%)。
(1-2)化合物HT-9的合成:
在氮气氛围下,向三口烧瓶中依次加入50mL无水甲苯、化合物MA-9(2.5g,7.5mmol,1eq)和N-苯基-4-联苯胺(4.6g,18.8mmol,2.5eq),将混合物充分搅拌,再分别加入叔丁醇钠(1.1g,11.3mmol,1.5eq),双二亚苄基丙酮钯(34mg,0.05mmol,0.7%eq),和三叔丁基膦(10%正己烷溶液,0.26mL,0.11mmol,1.5%eq)。加热回流12小时后,通过薄层色谱法分析基本无原料化合物MA-9剩余,停止加热。当降温至45℃以下时,向反应体系加入5mL浓盐酸(37%H2O)和100mL去离子水的混合溶液,用分液漏斗分液,保留有机相,水相用甲苯(3×50mL)萃取,与前述保留有机相合并,蒸馏去除溶剂,粗产品依次经过硅胶柱层析分离(流动相为正己烷/二氯甲烷混合溶剂),和乙醇/正己烷的混合溶剂重结晶,得到化合物HT-9(4.5g,收率83.0%)。两步反应总收率65.0%,质谱(m/z)=751.40[M+H]+。
参照化合物HT-9的制备方法合成化合物HT-2、HT-14、HT-36、HT-48、HT-54、HT-76、HT-78、HT-82、HT-85、HT-87、HT-104、HT-114,不同之处在于使用原料ii-x等当量地代替6-溴-1,1,4,4-四甲基-1,2,3,4-四氢化萘,使用原料iii-x等当量地代替N-苯基-4-联苯胺,其中使用的主要原料、合成的中间体及其收率如表1所示。
表1
(2)化合物HT-66的合成:
(2-1)中间体化合物MA-66的合成:
在氮气氛围下,依次将2-溴-4-氯-苯硼酸(2.3g,9.8mmol,1eq)、6-碘-1,4-苯并恶烷(2.6g,9.8mmol,1eq)、四(三苯基膦)钯(113.2mg,0.1mmol,1%eq)、碳酸钾(3.0g,21.6mmol,2.2eq)、四丁基溴化铵(632mg,2.0mmol,0.2eq)、脱气处理的甲苯(40mL)、乙醇(10mL)和去离子水(10mL)加入三口烧瓶中。氮气氛围下升温至回流,搅拌12小时后停止加热。将反应体系冷却至室温,倒入乙酸乙酯(3×70mL)进行萃取,合并有机相,使用无水硫酸镁进行干燥,过滤,减压除去溶剂;所得粗产品经过乙醇/正庚烷混合溶剂体系重结晶提纯,得到化合物MA-66(2.5g,收率78.6%)。
(2-2)中间体化合物MB-66的合成:
在氮气氛围下,向三口烧瓶中依次加入化合物MA-66(2.4g,7.4mmol,1eq)、胺类化合物iii-66(2.1g,7.4mmol,1eq)、叔丁醇钠(840mg,8.8mmol,1.2eq)、双(三叔丁基膦)钯(75.6mg,0.15mmol,2%mol),和无水甲苯(50mL),搅拌并升温至回流。8小时后停止加热,将反应体系冷却至室温,使用二氯甲烷(3×60mL)进行萃取,合并有机相,使用无水硫酸镁进行干燥,过滤,减压除去溶剂;所得粗品依次经过硅胶柱色谱提纯(流动相为正己烷/二氯甲烷混合溶剂),和乙醇/正己烷混合溶剂体系重结晶提纯,得到化合物MB-66(2.9g,74.2%)。
(2-3)化合物HT-66的合成:
在氮气氛围下,向三口烧瓶中依次加入40mL无水甲苯、化合物MA-66(2.7g,5.1mmol,1eq)和N-苯基-4-联苯胺(1.8g,5.6mmol,1.1eq),将混合物充分搅拌,再分别加入叔丁醇钠(733mg,7.6mmol,1.5eq),双二亚苄基丙酮钯(34mg,0.05mmol,1%eq),和三叔丁基膦(10%正己烷溶液,0.18mL,0.077mmol,1.5%eq)。加热回流12小时后,通过薄层色谱法分析基本无原料化合物MB-66剩余,停止加热。当降温至45℃以下时,向反应体系加入5mL浓盐酸(37%H2O)和90mL去离子水的混合溶液,用分液漏斗分液,保留有机相,水相用甲苯(3×50mL)萃取,与前述保留有机相合并,蒸馏去除溶剂,粗产品依次经过硅胶柱层析分离(流动相为正己烷/二氯甲烷混合溶剂),和乙醇/正己烷的混合溶剂重结晶,得到化合物HT-66(3.4g,收率81.9%)。三步反应总收率47.8%,质谱(m/z)=815.36[M+H]+
参照化合物HT-66的制备方法合成化合物HT-16、HT-24、HT-29、HT-42、HT-50、HT-119和HT-121,不同之处在于使用原料ii-x等当量地代替6-碘-1,4-苯并恶烷,使用原料iii-x等当量地代替N-苯基-2(9,9-二甲基-9H-芴)胺,使用原料iv-x等当量地代替二(4-联苯基)胺,其中使用的主要原料、合成的中间体及其收率如表2所示。
表2
(3)化合物HT-164的合成:
(3-1)中间体化合物MA-164的合成:
参照化合物MA-9的制备方法合成中间体化合物MA-164。不同之处在于,使用原料3,5-二氯苯硼酸等当量地代替2-溴-4-氯-苯硼酸,使用原料4-溴-1,2-亚甲二氧基苯(ii-164)等当量地代替6-溴-1,1,4,4-四甲基-1,2,3,4-四氢化萘(ii-9)。
(3-2)中间体化合物MB-164的合成:
参照从中间体化合物MB-9制备得到化合物HT-9的方法合成中间体化合物MB-164。不同之处在于,使用中间体化合物MA-164等当量地代替化合物MB-9;使用胺类化合物iii-164代替N-苯基-4-联苯胺(iv-9),并且iii-164与MA-164的物质的量之比为1:1。
(3-3)化合物HT-164的合成:
参照从中间体化合物MB-9制备得到化合物HT-9的方法合成化合物HT-164。不同之处在于,使用中间体化合物MB-164等当量地代替化合物MB-9;使用胺类化合物iv-164代替iv-9,并且iii-164与MA-164的物质的量之比为1:1,三步反应总收率45.4%,质谱(m/z)=855.35[M+H]+
参照HT-164的方法合成化合物HT-132、HT-141、HT-152、HT-158、HT-159、HT-171、HT-176、HT-181、HT-184、HT-192、HT-194、HT-203、HT-207、HT-214、HT-215、HT-219、HT-220、HT-225、HT-230,不同之处在于使用原料ii-x等当量地代替ii-164,使用原料iii-x等当量地代替iii-164,使用原料iv-x等当量地代替iv-164,其中使用的主要原料、合成的中间体及其收率如表3所示。
表3
(4)化合物HT-247的合成:
(4-1)中间体化合物MA-247的合成:
参照化合物MA-66的制备方法合成中间体化合物MA-247。不同之处在于,使用原料4-溴-2-氯苯硼酸等当量地代替2-溴-4-氯-苯硼酸,使用原料5-碘-2,3-二氢苯并呋喃(ii-247)等当量地代替6-碘-1,4-苯并恶烷(ii-66)。
(4-2)中间体化合物MB-247的合成:
在氮气氛围下,向三口烧瓶中依次加入化合物MA-247(3.1g,10.0mmol,1eq),化合物iii-247(3.8g,10.0mmol,1eq),碳酸钾(3.5g,25.0mmol,2.5eq),四(三苯基膦)钯(57.8mg,0.05mmol,0.5%eq),以及脱气的甲苯(50mL)、乙醇(30mL)和水(20mL)。开启搅拌,并在氮气氛围下升温至回流,反应15小时,通过薄层色谱法分析基本无原料剩余,停止加热。冷却至室温后倒入80mL甲苯中,静置分层,用甲苯(3×80mL)萃取,合并所得有机相并用无水硫酸镁干燥,过滤并减压蒸馏除去溶剂。将所得粗产品经过硅胶柱层析分离(流动相为正己烷/二氯甲烷混合溶剂),得到化合物MB-247(4.2g,收率74.3%)。
(4-3)化合物HT-247的合成:
参照化合物HT-66的制备方法合成化合物HT-247,不同之处在于使用原料化合物MB-247等当量地代替化合物HT-66,使用原料化合物iv-247等当量地代替N-苯基-4-联苯胺(iv-66)。三步总收率42.9%,质谱(m/z)=875.39[M+H]+
参照化合物HT-247的方法合成化合物HT-243、HT-244、HT-252、HT-254、HT-262、HT-264、HT-269、HT-270、HT-272、HT-276、HT-278、HT-283、HT-284、HT-285、HT-292、HT-297、HT-299、HT-305、HT-311,不同之处在于化合物HT-243,HT-254,HT-270,HT-284,HT-311使用原料2-溴-4-氯-苯硼酸等当量地代替4-溴-2-氯苯硼酸,以及化合物HT-262,HT-264,HT-276,HT-283,HT-292,HT-297,HT-299,HT-305中使用原料3,5-二氯苯硼酸等当量地代替4-溴-2-氯苯硼酸。上述化合物全部使用原料ii-x等当量地代替ii-247,使用原料iii-x等当量地代替iii-247,使用原料iv-x等当量地代替iv-247,其中使用的主要原料、合成的中间体及其收率如表4-6所示(表5中化合物的合成起始原料为2-溴-4-氯-苯硼酸、表6中化合物的合成起始原料为3,5-二氯苯硼酸)。
表4
表5
表6
(5)化合物HT-258的合成:
(5-1)中间体化合物MA-258的合成:
参照化合物MA-66的制备方法合成中间体化合物MA-258。不同之处在于,使用原料3,5-二溴苯硼酸等当量地代替2-溴-4-氯-苯硼酸,使用原料5-碘-1-甲基二氢吲哚(ii-258)等当量地代替6-碘-1,4-苯并恶烷(ii-66)。
(5-2)中间体化合物MB-258的合成:
参照化合物MB-247的制备方法合成中间体化合物MB-258。不同之处在于,使用原料化合物MA-258等当量地代替化合物MA-247,使用原料硼酸类化合物iii-258等当量地代替化合物iii-247。
(5-3)化合物HT-258的合成:
参照化合物MB-247的制备方法合成化合物HT-258。不同之处在于,使用原料化合物MB-258等当量地代替化合物MA-247,使用原料硼酸类化合物iV-258等当量地代替化合物iii-247,三步总收率48.1%,质谱(m/z)=892.33[M+H]+
参照化合物HT-258的方法合成化合物HT-251、HT-256,HT-271、HT-280、HT-282、HT-290、HT-295、HT-306、HT-308,不同之处在于化合物HT-251、HT-280、HT-290、HT-295、HT-306使用原料2,4-二溴苯硼酸等当量地代替3,5-二溴苯硼酸,使用原料ii-x等当量地代替ii-247,使用原料iii-x等当量地代替iii-247,使用原料iv-x等当量地代替iv-247,其中使用的主要原料、合成的中间体及其收率如表7-8所示(表8中化合物的合成起始原料为2,4-二溴苯硼酸)。
表7
表8
蓝光器件实施例1:蓝色有机电致发光器件的制备
按照如图2所示的结构制作蓝色顶部发光有机电致发光器件,制备工艺为:在玻璃材质的基底101上,形成透明阳极ITO膜层,膜厚150nm,得到第一电极102作为阳极,之后蒸镀化合物1与本发明化合物HT-2的混合材料作为空穴注入层103,混合比例为3:97(质量比),厚度为10nm,之后蒸镀100nm厚度的化合物HT-2,得到第一层空穴传输层104,然后蒸镀20nm厚度的化合物1-2,得到第二层空穴传输层105,然后以95:5的蒸镀速率蒸镀化合物1-3与化合物1-4(厚度30nm),制作蓝光发光单元106,然后依次蒸镀10nm厚度的化合物5形成空穴阻挡层107,以及混合比例为4:6(质量比)的化合物6和LiQ形成电子传输层108(厚度30nm)。之后依次将厚度为3nm厚度镱(Yb),厚度为10nm的镁(Mg)和银(Ag)以1∶9的蒸镀速率真空蒸镀在电子注入层上,作为第二电极109,随后蒸镀70nm的化合物7作为覆盖层材料,完成器件制作。
表9
蓝光器件实施例2-24
除了在形成空穴注入层和空穴传输层时,分别以表10中化合物替代化合物HT-2外,采用与蓝光器件实施例1相同的方法制作有机电致发光器件。
比较例1-2
除了在形成空穴注入层和空穴传输层时,分别以化合物HT-A、化合物HT-B替代化合物HT-2外,采用与蓝光器件实施例1相同的方法制作有机电致发光器件。
对如上制得的有机电致发光器件,其工作电压和效率通过计算机控制的Keithley2400测试***计算得到。黑暗条件下的器件寿命使用配备电源和光电二极管作为检测单元的Polaronix(McScience Co.)寿命测量***得到。每一组蓝光器件实施例和对比例2的器件均与对比例1的器件在同一批次中产出并测试,将对比例1的器件工作电压、效率和寿命均分别记为1,并分别计算蓝光器件实施例1-24、对比例1和对比例2的器件相应指标的比值,如表10所示。
表10
空穴传输层 | 相对工作电压 | 相对效率 | 相对寿命 | |
对比例1 | HT-A | 1 | 1 | 1 |
对比例2 | HT-B | 0.965 | 0.980 | 0.922 |
蓝光器件实施例1 | HT-2 | 0.875 | 1.185 | 1.279 |
蓝光器件实施例2 | HT-16 | 0.894 | 1.126 | 1.321 |
蓝光器件实施例3 | HT-42 | 0.871 | 1.089 | 1.396 |
蓝光器件实施例4 | HT-48 | 0.900 | 1.194 | 1.379 |
蓝光器件实施例5 | HT-82 | 0.856 | 1.083 | 1.135 |
蓝光器件实施例6 | HT-85 | 0.862 | 1.108 | 1.337 |
蓝光器件实施例7 | HT-104 | 0.950 | 1.086 | 1.286 |
蓝光器件实施例8 | HT-119 | 0.879 | 1.199 | 1.139 |
蓝光器件实施例9 | HT-141 | 0.840 | 1.128 | 1.152 |
蓝光器件实施例10 | HT-171 | 0.926 | 1.153 | 1.129 |
蓝光器件实施例11 | HT-176 | 0.884 | 1.100 | 1.150 |
蓝光器件实施例12 | HT-214 | 0.943 | 1.116 | 1.273 |
蓝光器件实施例13 | HT-225 | 0.833 | 1.090 | 1.147 |
蓝光器件实施例14 | HT-243 | 0.845 | 1.195 | 1.293 |
蓝光器件实施例15 | HT-247 | 0.905 | 1.168 | 1.356 |
蓝光器件实施例16 | HT-250 | 0.921 | 1.191 | 1.364 |
蓝光器件实施例17 | HT-256 | 0.927 | 1.113 | 1.352 |
蓝光器件实施例18 | HT-270 | 0.853 | 1.176 | 1.340 |
蓝光器件实施例19 | HT-272 | 0.862 | 1.140 | 1.200 |
蓝光器件实施例20 | HT-276 | 0.947 | 1.102 | 1.218 |
蓝光器件实施例21 | HT-280 | 0.941 | 1.119 | 1.178 |
蓝光器件实施例22 | HT-282 | 0.936 | 1.133 | 1.189 |
蓝光器件实施例23 | HT-283 | 0.929 | 1.182 | 1.125 |
蓝光器件实施例24 | HT-292 | 0.881 | 1.170 | 1.239 |
根据表10的结果可知,作蓝光器件的空穴传输层时,实施例1-24所使用的有机化合物与比较例1-2中使用的有机化合物形成的器件相比,电压降低了至少5%,发光效率至少提高了8%,寿命最少提高了12.5%。
红光器件实施例1:红色有机电致发光器件的制备
按照如图1所示的结构制作红色底部发光有机电致发光器件,制备工艺为:在玻璃材质的基底101上,形成透明阳极ITO膜层(厚度150nm),得到第一电极102作为阳极。随后通过真空蒸镀的方法,在阳极表面蒸镀表9中化合物1与表11中化合物2-2的混合材料作为空穴注入层103,混合比例为3:97(质量比),厚度为10nm。随后在空穴注入层上蒸镀100nm厚度的化合物2-2,得到第一层空穴传输层104。随后在第一空穴传输层上蒸镀10nm厚度的本发明化合物HT-9,得到第二层空穴传输层105。在第二空穴传输层上,将化合物2-3和化合物2-4以95:5的质量比进行共蒸镀,形成厚度为40nm的有机发光层106。然后,在有机发光层上,依次蒸镀化合物5形成空穴阻挡层107(厚度10nm),以及混合比例为4:6(质量比)的化合物6和LiQ形成电子传输层108(厚度30nm)。最后将镁(Mg)和银(Ag)以1∶9的蒸镀速率混合,真空蒸镀在电子注入层上,作为第二电极109,完成有机电致发光器件的制造。
红光器件实施例2-22
除了在形成第二空穴传输层时,分别以表12中化合物替代化合物HT-9外,采用与红光器件实施例1相同的方法制作有机电致发光器件。
比较例1-2
除了在形成第二空穴传输层时,分别以化合物HT-A、化合物HT-B替代化合物HT-13外,采用与红光器件实施例1相同的方法制作有机电致发光器件。
表11
对如上制得的有机电致发光器件,其工作电压和效率通过计算机控制的Keithley2400测试***计算得到。黑暗条件下的器件寿命使用配备电源和光电二极管作为检测单元的Polaronix(McScience Co.)寿命测量***得到。每一组红光器件实施例和对比例4的器件均与对比例3的器件在同一批次中产出并测试,将对比例3的器件的工作电压、效率和寿命均分别记为1,并分别计算红光器件实施例1-22、对比例4与对比例3的器件相应指标的比值,如表12所示。
表12
根据表12的结果可知,作红光器件的第二空穴传输层时,红光器件实施例1-22所使用的有机化合物与比较例1-2中使用的有机化合物形成的器件相比,电压均有所降低,发光效率均有所提高(最高达到20%),寿命提高了42%-99%。
绿光器件实施例1:绿色有机电致发光器件的制备
按照如图1所示的结构制作绿色底部发光有机电致发光器件,制备工艺为:在玻璃材质的基底101上,形成透明阳极ITO膜层(厚度150nm),得到第一电极102作为阳极。随后通过真空蒸镀的方法,在阳极表面蒸镀表9中所述化合物1与表11中化合物2-2的混合材料作为空穴注入层103,混合比例为3:97(质量比),厚度为10nm。随后在空穴注入层上蒸镀100nm厚度的化合物2-2,得到第一层空穴传输层104。随后在第一空穴传输层上蒸镀40nm厚度的本发明化合物HT-16,得到第二层空穴传输层105。在第二空穴传输层上,将化合物2-3和化合物2-4以90:10的质量比进行共蒸镀,形成厚度为40nm的有机发光层106。然后,在有机发光层上,依次蒸镀化合物5形成空穴阻挡层107(厚度10nm),以及混合比例为5:5(质量比)的化合物6和LiQ形成电子传输层108(厚度30nm)。最后将镁(Mg)和银(Ag)以1∶9的蒸镀速率混合,真空蒸镀在电子注入层上,作为第二电极109,完成有机电致发光器件的制造。
绿光器件实施例2-22
除了在形成第二空穴传输层时,分别以下表10中化合物替代化合物HT-16外,采用与绿光器件实施例1相同的方法制作有机电致发光器件。
比较例1
除了在形成第二空穴传输层时,以化合物HT-E替代化合物HT-16外,采用与绿光器件实施例1相同的方法制作有机电致发光器件。
表13
对如上制得的有机电致发光器件,其工作电压和效率通过计算机控制的Keithley2400测试***计算得到。黑暗条件下的器件寿命使用配备电源和光电二极管作为检测单元的Polaronix(McScience Co.)寿命测量***得到。每一组绿光器件实施例均与对比例5的器件在同一批次中产出并测试,将对比例5的器件的工作电压、效率和寿命均分别记为1,并分别计算绿光器件实施例1-22与对比例5的器件相应指标的比值,如表14所示。
表14
第二空穴传输层 | 相对工作电压 | 相对效率 | 相对寿命 | |
对比例5 | HT-E | 1 | 1 | 1 |
绿光器件实施例1 | HT-14 | 0.920 | 1.090 | 1.288 |
绿光器件实施例2 | HT-24 | 0.971 | 1.132 | 1.372 |
绿光器件实施例3 | HT-54 | 0.933 | 1.126 | 1.361 |
绿光器件实施例4 | HT-76 | 0.979 | 1.145 | 1.478 |
绿光器件实施例5 | HT-78 | 0.966 | 1.080 | 1.465 |
绿光器件实施例6 | HT-121 | 0.918 | 1.105 | 1.267 |
绿光器件实施例7 | HT-152 | 0.927 | 1.143 | 1.271 |
绿光器件实施例8 | HT-159 | 0.979 | 1.166 | 1.373 |
绿光器件实施例9 | HT-181 | 0.950 | 1.195 | 1.287 |
绿光器件实施例10 | HT-192 | 0.938 | 1.108 | 1.418 |
绿光器件实施例11 | HT-203 | 0.906 | 1.063 | 1.307 |
绿光器件实施例12 | HT-219 | 0.968 | 1.802 | 1.236 |
绿光器件实施例13 | HT-230 | 0.944 | 1.051 | 1.280 |
绿光器件实施例14 | HT-254 | 0.929 | 1.156 | 1.490 |
绿光器件实施例15 | HT-258 | 0.915 | 1.136 | 1.387 |
绿光器件实施例16 | HT-264 | 0.973 | 1.164 | 1.455 |
绿光器件实施例17 | HT-269 | 0.924 | 1.192 | 1.315 |
绿光器件实施例18 | HT-271 | 0.931 | 1.144 | 1.398 |
绿光器件实施例19 | HT-290 | 0.903 | 1.097 | 1.404 |
绿光器件实施例20 | HT-295 | 0.913 | 1.112 | 1.352 |
绿光器件实施例21 | HT-305 | 0.965 | 1.188 | 1.343 |
绿光器件实施例22 | HT-308 | 0.923 | 1.175 | 1.302 |
根据表14的结果可知,作绿光器件的第二空穴传输层时,实施例1-22所使用的有机化合物与比较例5中使用的有机化合物形成的器件相比,电压均有所降低,发光效率均有所提高,寿命提高了20%-49%。
综上可见,本发明的三芳胺化合物可以保证蓝光、红光和绿光的有机电致发光器件具有较高的空穴迁移率,并且能够有效的阻挡电子、激子进入到空穴传输层中,进而提高器件的效率,同时分子的稳定性高,能进一步提高器件的发光效率和使用寿命。
以上所述,仅为本发明较佳的具体实施方式,但本发明的保护范围并不局限于此,任何熟悉本技术领域的技术人员在本发明揭露的技术范围内,根据本发明的技术方案及其发明构思加以等同替换或改变,都应涵盖在本发明的保护范围之内。
Claims (14)
1.一种三芳胺化合物,该化合物具有如式(1)所示的结构:
在式(1)中,L1和L2相同或不相同,各自独立地选自单键、取代或未取代的亚苯基;
L11、L12、L21和L22相同或不相同,各自独立地选自单键、取代或未取代的C6-C30亚芳基、取代或未取代的C3-C30亚杂芳基;
Ar11、Ar12、Ar21和Ar22相同或不相同,各自独立地选自取代或未取代的C6-C30芳基、取代或未取代的C3-C30杂芳基;
基团A选自如2-a、2-b、2-c所示基团中的一种:
在式2-a至2-c中,Z1、Z2、Z3、Z4和Z5各自独立地选自-CR1R2-、-NR-、O或S;
R1和R2相同或不相同,各自独立地选自氢、氘、氘代或未氘代的甲基,满足在式2-a中Z1和Z3均为O和Z2为-CR1R2-时,R1和R2均不为氢和氘;
R选自取代或未取代的C1-C6烷基、取代或未取代的C1-C6杂烷基、取代或未取代的C3-C12环烷基、取代或未取代的C2-C12杂环烷基、取代或未取代的C6-C12芳基;
RA选自氢、氘、卤素、氰基、取代或未取代的C1-C12烷基、取代或未取代的C1-C12烷氧基、取代或未取代的C1-C12烷硫基、取代或未取代的C3-C18环烷基、取代或未取代的C2-C18杂环烷基、取代或未取代的C6-C30芳基、取代或未取代的C2-C30杂芳基;
n选自0、1、2或3,*表示连接位点。
2.根据权利要求1所述的三芳胺化合物,其特征在于,在式(1)中,Z1、Z2、Z3、Z4和Z5各自独立地选自-NR-、O或S且数量大于1时,满足任意两个选自-NR-、O或S的取代基之间间隔至少一个-CR1R2-。
3.根据权利要求1所述的三芳胺化合物,其特征在于,在式2-a中,当Z1和Z3均为O时,满足Z2为-CR1R2-且至少一个R1和R2为氘代或未取代的甲基。
4.根据权利要求1所述的三芳胺化合物,其特征在于,在式2-b中,当Z1、Z2、Z3和Z4均为-CR1R2-时,满足至少一个R1和R2为氘代或未取代的甲基。
5.根据权利要求1-4任一项所述的三芳胺化合物,其特征在于,在式(1)中,“取代或未取代的”的“取代的”表示被独立地选自由氘、卤素、氰基、硝基、C1-C12烷基、C3-C18环烷基、C1-C12烷氧基、C1-C12烷硫基、C6-C30芳基、C2-C30杂芳基中的一个或多个取代基所取代,且L1、L2、L11、L12、L21、L22、Ar11、Ar12、Ar21和Ar22中的取代基彼此相同或不相同。
7.根据权利要求1所述的三芳胺化合物,其特征在于,在式(1)中,L1和L2相同或不相同,各自独立地选自单键、取代或未取代的亚苯基,其中“取代或未取代的”的“取代的”表示被独立地选自氘、甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、甲氧基、乙氧基、甲硫基、乙硫基、环丁基、环戊基、环己基中的一个或多个取代基所取代,且L1、L2的取代基数量和种类相同或不相同。
8.根据权利要求1所述的三芳胺化合物,其特征在于,在式(1)中,L11、L12、L21和L22相同或不相同,各自独立地选自单键、取代或未取代的亚苯基、取代或未取代的亚萘基、取代或未取代的亚联苯基、取代或未取代的亚芴基、取代或未取代基的亚二苯并噻吩基、取代或未取代基的亚二苯并呋喃基,其中“取代或未取代的”的“取代的”表示被独立地选自选自氘、氟、氰基、甲基、乙基、正丙基、异丙基、叔丁基、甲氧基、乙氧基、甲硫基、乙硫基、环丁基、环戊基、环己基、苯基、萘基、联苯基、二苯并呋喃基、二苯并噻吩基、咔唑基中的一个或多个取代基所取代,且L11、L12、L21和L22的取代基数量和种类相同或不相同。
9.根据权利要求1所述的三芳胺化合物,其特征在于,在式(1)中,Ar21和Ar22相同或不相同,各自独立地选自取代或未取代的苯基、取代或未取代的萘基、取代或未取代的噻吩基、取代或未取代的呋喃基、取代或未取代的硒吩基、取代或未取代的苯并噻吩基、取代或未取代的苯并呋喃基、取代或未取代的苯并硒吩基、取代或未取代的二苯并噻吩基、取代或未取代的二苯并呋喃基、取代或未取代的二苯并硒吩基、取代或未取代的芴基、取代或未取代的硅芴基、取代或未取代的咔唑基、取代或未取代的苯并萘并噻吩基、取代或未取代的苯并萘并呋喃基、取代或未取代的苯并萘并硒吩基、取代或未取代的苯并芴基、取代或未取代的苯并咔唑基,且其中“取代或未取代的”的“取代的”表示被独立地选自氘、氟、氰基、三甲基硅基、三氟甲基、C1-C6烷基、C4-C6环烷基、C1-C6烷氧基、C1-C6烷硫基、C6-C14芳基、C5-C14杂芳基中的一个或多个取代基所取代,且Ar11、Ar12、Ar21和Ar22的取代基数量和种类相同或不相同。
11.一种有机光电材料,包括权利要求1-10任一项所述三芳胺化合物中的一种或多种。
12.一种有机电致发光器件,包括权利要求1-10任一项所述三芳胺化合物中的一种或多种、或者权利要求11所述的有机光电材料。
13.根据权利要求12所述的有机电致发光器件,其特征在于,
包括基板、第一电极、包含发光层和空穴传输层在内的一层以上有机层和第二电极元件;
所述空穴传输层材料含有权利要求1-10任一项所述有机化合物中的一种或多种、或者权利要求14所述的有机光电材料。
14.一种显示或照明装置,其特征在于,其包括权利要求12或13所述的有机电致发光器件。
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