WO2023207992A1 - Indole derivative, organic electroluminescent element, display device, and lighting device - Google Patents
Indole derivative, organic electroluminescent element, display device, and lighting device Download PDFInfo
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- WO2023207992A1 WO2023207992A1 PCT/CN2023/090633 CN2023090633W WO2023207992A1 WO 2023207992 A1 WO2023207992 A1 WO 2023207992A1 CN 2023090633 W CN2023090633 W CN 2023090633W WO 2023207992 A1 WO2023207992 A1 WO 2023207992A1
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- substituted
- unsubstituted
- indole derivative
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- 150000002475 indoles Chemical class 0.000 title claims abstract description 27
- 239000010410 layer Substances 0.000 claims description 85
- 125000003118 aryl group Chemical group 0.000 claims description 30
- 125000001072 heteroaryl group Chemical group 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 15
- 229910052805 deuterium Inorganic materials 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- -1 dibenzofuranyl Chemical class 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 125000005842 heteroatom Chemical group 0.000 claims description 9
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims description 6
- 125000005264 aryl amine group Chemical group 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 239000012044 organic layer Substances 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 125000006761 (C6-C60) arylene group Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 235000010290 biphenyl Nutrition 0.000 claims description 4
- 239000004305 biphenyl Substances 0.000 claims description 4
- 229910052796 boron Inorganic materials 0.000 claims description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
- 125000005549 heteroarylene group Chemical group 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 150000002825 nitriles Chemical class 0.000 claims description 4
- 229910052698 phosphorus Inorganic materials 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000002560 nitrile group Chemical group 0.000 claims description 3
- 238000006467 substitution reaction Methods 0.000 claims description 3
- 125000006751 (C6-C60) aryloxy group Chemical group 0.000 claims 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 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000320 amidine group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000005878 benzonaphthofuranyl group Chemical class 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 150000007942 carboxylates Chemical class 0.000 claims description 2
- 125000004988 dibenzothienyl group Chemical class C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 2
- 125000005597 hydrazone group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 2
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 2
- 125000000101 thioether group Chemical group 0.000 claims description 2
- 125000005580 triphenylene group Chemical group 0.000 claims description 2
- 125000005551 pyridylene group Chemical group 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 37
- 230000009477 glass transition Effects 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 230000002035 prolonged effect Effects 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 54
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 238000000034 method Methods 0.000 description 13
- 238000002360 preparation method Methods 0.000 description 13
- 238000002347 injection Methods 0.000 description 11
- 239000007924 injection Substances 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 230000000903 blocking effect Effects 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 230000005525 hole transport Effects 0.000 description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000007639 printing Methods 0.000 description 6
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 238000005859 coupling reaction Methods 0.000 description 5
- 125000000524 functional group Chemical group 0.000 description 5
- 239000005457 ice water Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 101100446506 Mus musculus Fgf3 gene Proteins 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000005401 electroluminescence Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 101100348848 Mus musculus Notch4 gene Proteins 0.000 description 3
- 101100317378 Mus musculus Wnt3 gene Proteins 0.000 description 3
- NSGDYZCDUPSTQT-UHFFFAOYSA-N N-[5-bromo-1-[(4-fluorophenyl)methyl]-4-methyl-2-oxopyridin-3-yl]cycloheptanecarboxamide Chemical compound Cc1c(Br)cn(Cc2ccc(F)cc2)c(=O)c1NC(=O)C1CCCCCC1 NSGDYZCDUPSTQT-UHFFFAOYSA-N 0.000 description 3
- 101000767160 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) Intracellular protein transport protein USO1 Proteins 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 3
- 229910000024 caesium carbonate Inorganic materials 0.000 description 3
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 125000003367 polycyclic group Chemical group 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 238000010189 synthetic method Methods 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- RYBUOOWVRQLZAG-UHFFFAOYSA-N 1-bromo-11H-benzo[a]carbazole Chemical compound BrC1=CC=CC=2C1=C1NC3=CC=CC=C3C1=CC=2 RYBUOOWVRQLZAG-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 101150003085 Pdcl gene Proteins 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- LNAMMBFJMYMQTO-FNEBRGMMSA-N chloroform;(1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].ClC(Cl)Cl.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 LNAMMBFJMYMQTO-FNEBRGMMSA-N 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 239000002120 nanofilm Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- OEWYVHJLQDINFS-UHFFFAOYSA-N 2-(2-aminoethyl)aniline Chemical compound NCCC1=CC=CC=C1N OEWYVHJLQDINFS-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- SFKMVPQJJGJCMI-UHFFFAOYSA-N 2-chloro-4-phenylquinazoline Chemical compound C=12C=CC=CC2=NC(Cl)=NC=1C1=CC=CC=C1 SFKMVPQJJGJCMI-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- UIIJZQVROQHLAP-UHFFFAOYSA-N 2-methyl-2-(2-methylbutan-2-yloxy)butane;sodium Chemical compound [Na].CCC(C)(C)OC(C)(C)CC UIIJZQVROQHLAP-UHFFFAOYSA-N 0.000 description 1
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 1
- RXELBMYKBFKHSM-UHFFFAOYSA-N 2-phenyl-1,3,5-triazine Chemical compound C1=CC=CC=C1C1=NC=NC=N1 RXELBMYKBFKHSM-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
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- SNFCXVRWFNAHQX-UHFFFAOYSA-N 9,9'-spirobi[fluorene] Chemical compound C12=CC=CC=C2C2=CC=CC=C2C21C1=CC=CC=C1C1=CC=CC=C21 SNFCXVRWFNAHQX-UHFFFAOYSA-N 0.000 description 1
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- 239000012159 carrier gas Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
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- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
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- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910000103 lithium hydride Inorganic materials 0.000 description 1
- 238000001459 lithography Methods 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- JKDRQYIYVJVOPF-FDGPNNRMSA-L palladium(ii) acetylacetonate Chemical compound [Pd+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O JKDRQYIYVJVOPF-FDGPNNRMSA-L 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- ZLMJMSJWJFRBEC-OUBTZVSYSA-N potassium-40 Chemical compound [40K] ZLMJMSJWJFRBEC-OUBTZVSYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 238000005092 sublimation method Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- BZHGXQBPJUHVFW-UHFFFAOYSA-N toluene;tritert-butylphosphane Chemical compound CC1=CC=CC=C1.CC(C)(C)P(C(C)(C)C)C(C)(C)C BZHGXQBPJUHVFW-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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Classifications
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- 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
- C07D471/12—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 three hetero rings
- C07D471/16—Peri-condensed systems
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
Definitions
- the invention belongs to the technical field of organic electroluminescent materials, and specifically relates to an indole derivative, an organic electroluminescent element, a display device and a lighting device.
- Organic electroluminescence is mainly divided into fluorescence and phosphorescence.
- the probability of singlet excitons and triplet excitons is 1:3, which is the theoretical limit of fluorescence from singlet exciton radiation transition. is 25%, and the theoretical limit of fluorescence from triplet exciton radiative transition is 75%. How to utilize the energy of 75% of triplet excitons has become a top priority.
- Forrest et al. discovered that the phosphorescent electroluminescence phenomenon broke through the 25% quantum efficiency limit of organic electroluminescent materials, which attracted widespread attention to metal complex phosphorescent materials. Since then, people have conducted a lot of research on phosphorescent materials.
- the present invention provides an indole derivative, an organic electroluminescent element, a display device and a lighting device.
- the indole derivative according to the present invention as a raw material for organic electroluminescent element materials, can provide organic electroluminescent element materials and organic electroluminescent elements with reduced starting voltage, high luminous efficiency, and improved brightness.
- W 1 and W 2 represent groups represented by formula (II);
- Z independently represents CR 0 or N
- R 0 , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 are each independently selected from hydrogen, deuterium, halogen, nitrile, and C 1 -C 40 alkane.
- Ar 1 is selected from the group consisting of substituted or unsubstituted C 6 -C 60 aryl group and substituted or unsubstituted C 2 -C 60 heteroaryl group;
- L is selected from the group consisting of substituted or unsubstituted C 6 -C 60 arylene, substituted or unsubstituted C 2 -C 60 heteroarylene.
- An aryl group in the sense of the present invention contains 6 to 60 carbon atoms, and a heteroaryl group in the sense of the present invention contains 2 to 60 carbon atoms and at least one heteroatom, provided that the sum of the carbon atoms and heteroatoms is at least 5 ;
- the heteroatom is preferably selected from N, O or S.
- Aryl or heteroaryl groups here encompass both monocyclic groups and polycyclic systems.
- a polycyclic ring may have two carbons common to two adjacent rings or referred to as "fused" to two or more rings, where at least one of the rings is aromatic, for example the other rings may be cyclic Alkyl, cycloalkenyl, aryl, heterocycle and/or heteroaryl.
- aryl or heteroaryl groups can also be linked by non-aromatic units such as C, N, O or S atoms, for example, as in systems in which two or more aryl groups are linked by, for example, short alkyl groups. , such as fluorene, 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamine, diaryl ether, dibenzofuran or dibenzothiophene, etc.
- the alkyl group used in the present invention refers to a monovalent functional group obtained by removing one hydrogen atom from a linear or branched saturated hydrocarbon with a carbon number of 1 to 40.
- a monovalent functional group obtained by removing one hydrogen atom from a linear or branched saturated hydrocarbon with a carbon number of 1 to 40.
- Heteroalkyl means that the hydrogen atom or -CH2- on the alkyl group is replaced by at least one heteroatom, and the heteroatom is selected from halogen, nitrile, N, O, S or silicon.
- the alkenyl group used in the present invention refers to a monovalent functional group obtained by removing one hydrogen atom from a straight-chain or branched-chain unsaturated hydrocarbon having one or more carbon-carbon double bonds with a carbon number of 2 to 40.
- a monovalent functional group obtained by removing one hydrogen atom from a straight-chain or branched-chain unsaturated hydrocarbon having one or more carbon-carbon double bonds with a carbon number of 2 to 40.
- the alkynyl group used in the present invention refers to a monovalent functional group obtained by removing one hydrogen atom from a straight-chain or branched-chain unsaturated hydrocarbon with more than one carbon-carbon triple bond and a carbon number of 2 to 40.
- a monovalent functional group obtained by removing one hydrogen atom from a straight-chain or branched-chain unsaturated hydrocarbon with more than one carbon-carbon triple bond and a carbon number of 2 to 40.
- cycloalkyl and cycloalkenyl refer to a monovalent functional group obtained by removing one hydrogen atom from a monocyclic or polycyclic non-aromatic hydrocarbon with a carbon number of 3 to 40.
- cyclopropyl cyclobutyl, cyclopentyl, cyclohexyl, norbornyl, adamantyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptyl, Cycloheptenyl, in which one or more -CH 2 - groups can be replaced by the above-mentioned groups; in addition, one or more hydrogen atoms can also be replaced by deuterium atoms, halogen atoms or nitrile groups.
- the heterocycloalkyl group used in the present invention refers to a monovalent functional group obtained by removing one hydrogen atom from a non-aromatic hydrocarbon with a nuclear number of 3 to 40.
- more than one carbon in the ring preferably 1 to 3 carbons, are substituted by heteroatoms such as N, O or S.
- heteroatoms such as N, O or S.
- ком ⁇ онент or “group” means that one or more members of an applicable list are combined to form a known or chemically stable arrangement that one of ordinary skill in the art would contemplate from the applicable list.
- alkyl and deuterium can be combined to form partially or fully deuterated alkyl
- halogen and alkyl can be combined to form haloalkyl substituents, such as trifluoromethyl, etc.
- halogen, alkyl, and aryl can be combined to form Haloaralkyl.
- indole derivative is selected from the group consisting of formula I-1 or formula I-2:
- each of Z is independently CR 0 ;
- Ar 1 is selected from substituted or unsubstituted C 2 -C 60 heteroaryl
- L is selected from the group consisting of substituted or unsubstituted C 6 -C 60 arylene, substituted or unsubstituted C 2 -C 60 heteroarylene;
- R 0 , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 are each independently selected from the group consisting of: hydrogen, deuterium, substituted or unsubstituted C 6 -C 60 aryl or substituted or unsubstituted C 2 -C 60 heteroaryl.
- heteroaryl group is selected from the group consisting of the following groups shown in II-1 to II-17:
- Z 1 and Z 2 are each independently selected from hydrogen, deuterium, halogen, hydroxyl, nitrile group, nitro group, amino group, amidine group, hydrazine group, hydrazone group, carboxyl group or its carboxylate, sulfonic acid group or its sulfonate , phosphate group or its phosphate, C 1 -C 40 alkyl group, C 2 -C 40 alkenyl group, C 2 -C 40 alkynyl group, C 1 -C 40 alkoxy group, C 3 -C 40 cycloalkyl group, C 3 -C 40 cycloalkenyl group, substituted or unsubstituted C 6 -C 60 aryl group, substituted or unsubstituted C 6 -C 60 aryloxy group, substituted or unsubstituted C 6 -C 60 aryl sulfide group , or a group consisting of substituted or unsubstituted C 2 -
- T 1 means O, S, CR'R" or NAr';
- R', R" are each independently selected from hydrogen, deuterium, C 1 to C 40 alkyl group, C 1 to C 40 heteroalkyl group, substituted or unsubstituted C 6 to C 60 aryl group, substituted or unsubstituted A group consisting of C 6 -C 60 arylamine groups, or substituted or unsubstituted C 2 -C 60 heterocyclic aryl groups, R' and R" can optionally be joined or fused to form another multiple substituted Or an unsubstituted ring, containing or not containing one or more heteroatoms N, P, B, O or S in the formed ring; preferably, R', R" is methyl, phenyl or fluorenyl;
- Ar' is selected from C 1 to C 40 alkyl, C 1 to C 40 heteroalkyl, C 3 to C 40 cycloalkyl, substituted or unsubstituted C 6 -C 60 aryl, substituted or unsubstituted A group consisting of a C 6 -C 60 fused ring aryl group, a substituted or unsubstituted C 6 -C 60 arylamine group, or a substituted or unsubstituted C 2 -C 60 heterocyclic aryl group; preferably, Ar' is methyl, ethyl, phenyl, biphenyl or naphthyl;
- Ar 1 is selected from the group consisting of the following groups III-1 to III-18:
- T 2 is selected from O or S;
- R 10 and R 11 are each independently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted C 6 to C 60 aryl groups, and substituted or unsubstituted C 2 to C 60 heteroaryl groups;
- R 12 is selected from the group consisting of hydrogen, deuterium, C 1 to C 40 alkyl, substituted or unsubstituted C 6 -C 60 aryl, or substituted or unsubstituted C 2 -C 60 heteroaryl; R 12 is one or more saturated substitutions;
- R 10 and R 11 are each independently selected from phenyl, biphenyl, terphenyl, naphthyl, phenanthrenyl, triphenylene, naphthalene-substituted phenyl, phenanthrene-substituted phenyl base, dibenzofuranyl, dibenzothienyl, carbazolyl, dibenzofuran-substituted phenyl, dibenzothiophene-substituted phenyl, phenyl-substituted carbazolyl, naphthyl-substituted carbazole group consisting of a biphenyl-substituted carbazolyl group, a 9-phenylcarbazolyl group, a benzonaphthofuranyl group, a benzonaphthothienyl group or a phenyl-substituted benzocarbazoly
- R 12 is hydrogen or deuterium.
- the L is selected from a single bond, a phenylene group, a pyridinyl group or a naphthalenediyl group.
- the R 0 , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are all hydrogen.
- carbazole derivative is one of the following structures shown in N313 ⁇ N582:
- *-T 3 -* is each independently selected from *-O-*, *-S-* or one of the following structures:
- the present invention provides a method for preparing the compound of formula (I), taking the following scheme 1 and scheme 2 as examples:
- the compound of formula (I) is prepared by a palladium-catalyzed or base-catalyzed coupling reaction from compound C1 or C2 having a parent core structure and compound D containing an acceptor substituent.
- a palladium catalyst that can be used for palladium-catalyzed coupling reaction, it can be selected from: Pd(P- t Bu 3 ) 2 , Pd(PPh 3 ) 4 , Pd 2 (dba) 3 , Pd 2 (dba) 3 CHCl 3 , PdCl 2 (PPh 3 ) 2 , PdCl 2 (CH 3 CN) 2 , Pd(OAc) 2 , Pd(acac) 2 , Pd/C, PdCl 2 , [Pd(allyl)Cl] 2, etc., or use two mixture of one or more species.
- the base used in the palladium-catalyzed coupling reaction or the base-catalyzed coupling reaction can be selected from: sodium tert-butoxide, potassium tert-butoxide, sodium hydride, lithium hydride, sodium tert-amyloxide, sodium ethoxide, sodium methoxide, carbonic acid Sodium, potassium carbonate, cesium carbonate, lithium, potassium hydride, triethylamine, cesium fluoride, etc., as well as one or a mixture of two or more thereof.
- the coupling reaction can be carried out in an organic solvent, wherein the organic solvent can be selected from: diethyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-dioxane, ethylene glycol ethyl ether, ethylene glycol diethyl ether, ethylene glycol Ether solvents such as methyl ether, diglyme, or anisole, aromatic hydrocarbon agents such as benzene, toluene, and xylene, chlorobenzene, dichlorobenzene, N,N-dimethylformamide, N,N- One type or a mixture of two or more types of dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide, sulfolane, etc. can be used.
- the organic solvent can be selected from: diethyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-dioxane, ethylene glycol
- Compound D can be prepared using conventional organic reactions or can be obtained from commercial sources.
- the present invention provides an organic electroluminescent element, including a first electrode, a second electrode, a capping layer and at least one organic layer placed between the first electrode and the second electrode, the organic layer or At least one layer of the capping layer includes the indole derivative.
- the organic electroluminescent element includes a cathode, an anode and at least one light-emitting layer. In addition to these layers, it may contain further layers, for example in each case one or more hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, excitation layers, etc. sub-blocking layer, electron blocking layer and/or charge generating layer. An intermediate layer having, for example, an exciton blocking function can also be introduced between the two luminescent layers. However, it should be noted that each of these layers does not necessarily have to be present.
- the organic electroluminescent device described herein may include one light emitting layer, or it may include multiple light emitting layers.
- a plurality of light-emitting compounds capable of emitting light are used in the light-emitting layer.
- Particularly preferred are systems with three luminescent layers, wherein the three layers can exhibit blue, green and red luminescence. If more than one luminescent layer is present, according to the invention at least one of these layers contains an indole derivative according to the invention.
- organic electroluminescent components are preferred in which one or more layers are applied by means of a sublimation method, wherein the layer is deposited by vapor deposition in a vacuum sublimation device at an initial pressure of less than 10 -5 Pa, preferably less than 10 -6 Pa. Apply the material.
- the initial pressure may also be even lower, for example below 10 -7 Pa.
- organic electroluminescent elements in which one or more layers are applied by means of an organic vapor deposition method or by means of carrier gas sublimation, wherein the material is applied at a pressure of between 10 ⁇ 5 Pa and 1 Pa.
- a particular example of this method is the organic vapor jet printing method, in which the material is applied directly through a nozzle and is therefore structured.
- organic electroluminescent elements produced from solution, for example by spin coating, or by means of any desired printing method, such as screen printing, flexographic printing, lithography, photothermography, thermal transfer printing, spray printing, etc. Ink printing or nozzle printing to produce one or more layers.
- Soluble compounds can be obtained, for example, by appropriately substituting compounds represented by formula (I). These methods are also particularly suitable for oligomers, dendrimers and polymers.
- hybrid methods are possible, in which one or more layers are applied, for example, from solution and one or more further layers are applied by vapor deposition.
- the organic layer further includes at least one selected from the group consisting of an electron injection layer, an electron transport layer, a hole blocking layer, an electron blocking layer, a hole transport layer, a hole injection layer, a light emitting layer, and a photorefractive layer.
- the organic electroluminescent element of the present invention can be either a top-emitting light-emitting element or a bottom-emitting light-emitting element.
- the structure and preparation method of the organic electroluminescent element of the present invention are not limited.
- the organic electroluminescent element prepared by using the compound of the present invention can reduce the starting voltage and improve the luminous efficiency and brightness.
- a display device includes the organic electroluminescent element.
- a lighting device includes the organic electroluminescent element.
- the material for organic devices of the present invention contains the indole derivative of the present invention.
- the material for organic elements may be composed of the compound of the present invention alone or may contain other compounds.
- the indole derivative of the present invention contained in the material for organic electroluminescent elements of the present invention can be used as a host material.
- the material for organic electroluminescence elements of the present invention may contain other compounds as doping materials.
- the material for organic electroluminescent elements of the present invention can also be used as a material for a hole transport layer, an enhancement layer, a light emitting layer, an electron transport layer, a charge generation layer, an electron blocking layer, a capping layer or a photorefractive layer.
- the invention also relates to mixtures comprising at least one compound of formula (I) or the preferred embodiments described above and at least one further compound. If the compounds according to the invention are used as matrix materials, the other compounds can be fluorescent or phosphorescent emitters. The mixture may then additionally contain other materials as additional matrix materials.
- the invention also relates to the use of the compounds of the invention in electronic components. Preferably, as mentioned above and below, the compounds according to the invention are used in electron transport layers or as matrix materials in light-emitting layers.
- the compounds according to the invention and the electronic components obtainable therefrom, in particular organic electroluminescent components differ from the prior art by one or more of the following surprising advantages:
- the electronic components obtainable using the compounds of the present invention exhibit high efficiency, especially high luminous efficiency and high external quantum efficiency.
- the compounds of the present invention provide low operating voltage.
- the compounds according to the invention can be processed using conventional methods, so that cost advantages can also be achieved.
- the films obtainable using the compounds of the present invention exhibit excellent qualities, especially in terms of film uniformity.
- the compounds of the invention can be produced in a very fast and easy manner using conventional methods, so that cost advantages can also be achieved.
- FIG. 1 shows a schematic diagram of an organic light-emitting device 100. Illustrations are not necessarily to scale.
- Device 100 may include substrate 101, anode 102, hole injection layer 103, hole transport layer 104, electron blocking layer 105, light emitting layer 106, hole blocking layer 107, electron transport layer 108, electron injection layer 109, cathode 110 and capping layer (CPL) 111.
- Device 100 may be fabricated by sequentially depositing the described layers.
- FIG. 2 shows a schematic diagram of an organic light-emitting device 200 with two light-emitting layers.
- the device includes a substrate 201, an anode 202, a hole injection layer 203, a hole transport layer 204, a first light-emitting layer 205, an electron transport layer 206, a charge generation layer 207, a hole injection layer 208, and a hole transport layer 209. , the second light-emitting layer 210, the electron transport layer 211, the electron injection layer 212 and the cathode 213.
- Device 200 may be prepared by sequentially depositing the described layers.
- the luminescence peak shapes of the first luminescent layer and the second luminescent layer may be overlapping or cross-overlapping or non-overlapping.
- materials similar to those described with respect to device 100 may be used.
- Figure 2 provides an example of how some layers may be added from the structure of device 100.
- Luminance and chromaticity coordinates tested using spectral scanner PhotoResearch PR-715;
- Life test Use LTS-1004AC life test device.
- the preparation method of compound N315 includes the following steps:
- the preparation of compound N430 includes the following steps:
- compound C is used as a hole injection material
- compound D is used as a hole transport material
- compound E is used as a red light host material
- compound F is used as a red light doping material
- compound G is used as an electron transport doping material
- LiQ is used as an electron transport material Subject material.
- the EL evaporation machine manufactured by DOV Company was used to evaporate onto the ITO glass in order to produce the OLED contrast element 1.
- a digital source meter and a luminance meter were used to measure the driving voltage and current efficiency of the organic electroluminescent elements prepared in Test Example 1 and Comparative Example 1, as well as the lifetime of the elements. Specifically, increase the voltage at a rate of 0.1V per second, measure the voltage when the brightness of the organic electroluminescent element reaches 1000cd/ m2 , which is the driving voltage, and measure the current density at this time; the ratio of brightness to current density That is the current efficiency; the LT90% life test is as follows: use a luminance meter to maintain a constant current at a brightness of 1000cd/ m2 , and measure the time for the brightness of the organic electroluminescent element to decay to 900cd/ m2 , in hours.
- the current efficiency can reach more than 23.0cd/A, and the life span is greatly improved, making it a host material with good performance.
- Comparing Compound E in Comparative Example 1 with the compound of the present invention the difference lies in that the two joined carbazoles have a twisted configuration, greater steric hindrance, and weak planar conjugation ability.
- the compound of the present invention is a large planar conjugated structure in which benzocarbazole-joined indole has less steric hindrance and less impact on molecular film formation. Therefore, it has better molecular film formation and charge transport properties. Excellent, the charge transfer within the component is more balanced and the component performance is improved.
- Table 1 only lists the properties of some compounds among N313 ⁇ N582. The properties of other compounds are basically consistent with the data of the compounds listed in the table. Due to limited space, they will not be listed one by one.
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Abstract
The present invention relates to an indole derivative, an organic electroluminescent element, a display device, and a lighting device. The indole derivative of the present invention has a relatively high triplet level and a high glass transition temperature, and is suitable for being used as a material for the organic electroluminescent element. The material for the organic electroluminescent element containing the indole derivative has the characteristics of low starting voltage, high luminous efficacy, and high luminance. In addition, the indole derivative of the present invention has good thermal stability and film-forming performance, and is applied to the material for the organic electroluminescent element, the organic electroluminescent element, the display device, and the lighting device, such that the service life can be prolonged, thereby reducing the manufacturing costs of the material for the organic electroluminescent element, the organic electroluminescent element, the display device, and the lighting device.
Description
交叉引用cross reference
本申请要求2022年4月26日提交的专利名称为“一种吲哚衍生物、有机电致发光元件、显示装置和照明装置”的第202210445424.3号中国专利申请的优先权，其全部公开内容通过引用整体并入本文。This application claims the priority of Chinese patent application No. 202210445424.3, titled "An indole derivative, organic electroluminescent element, display device and lighting device" submitted on April 26, 2022, and its entire disclosure content is approved This reference is incorporated into this article in its entirety.
本发明属于有机电致发光材料技术领域，具体涉及一种吲哚衍生物、有机电致发光元件、显示装置和照明装置。The invention belongs to the technical field of organic electroluminescent materials, and specifically relates to an indole derivative, an organic electroluminescent element, a display device and a lighting device.
最近几年有机电致发光显示技术已趋于成熟，一些产品已进入市场，但在产业化过程中，仍有许多问题亟待解决，特别是用于制作元件的各种有机材料，其载流子注入、传输性能，材料电发光性能、使用寿命、色纯度、各种材料之间及与各电极之间的匹配等，尚有许多问题还未解决。尤其是发光元件在发光效率和使用寿命方面还达不到实用化要求，这大大限制了OLED技术的发展。In recent years, organic electroluminescent display technology has become mature, and some products have entered the market. However, in the process of industrialization, there are still many problems that need to be solved urgently, especially the various organic materials used to make components. There are still many unresolved issues such as injection and transmission performance, material electroluminescence performance, service life, color purity, matching between various materials and between various electrodes. In particular, the luminous efficiency and service life of light-emitting components still do not meet practical requirements, which greatly limits the development of OLED technology.
有机电致发光主要分为荧光和磷光，但根据自旋量子统计理论，单重态激子和三重态激子的概率为1∶3，即来自单重态激子辐射跃迁的荧光的理论极限为25％，三重态激子辐射跃迁的荧光的理论极限为75％。如何利用75％的三线态激子的能量成为当务之急。1997年Forrest等发现磷光电致发光现象突破了有机电致发光材料量子效率25％效率的限制，引起人们对金属配合物磷光材料的广泛关注。从此，人们对磷光材料进行大量的研究。Organic electroluminescence is mainly divided into fluorescence and phosphorescence. However, according to the spin quantum statistical theory, the probability of singlet excitons and triplet excitons is 1:3, which is the theoretical limit of fluorescence from singlet exciton radiation transition. is 25%, and the theoretical limit of fluorescence from triplet exciton radiative transition is 75%. How to utilize the energy of 75% of triplet excitons has become a top priority. In 1997, Forrest et al. discovered that the phosphorescent electroluminescence phenomenon broke through the 25% quantum efficiency limit of organic electroluminescent materials, which attracted widespread attention to metal complex phosphorescent materials. Since then, people have conducted a lot of research on phosphorescent materials.
鉴于以上原因，特提出本发明。In view of the above reasons, the present invention is proposed.
发明内容Contents of the invention
为了解决现有技术存在的以上问题，本发明提供了一种吲哚衍生物、有机电致发光元件、显示装置和照明装置。本发明所述的吲哚衍生物作为有机电致发光元件用材料的原料，能够提供启动电压降低、发光效率高、亮度提高的有机电致发光元件用材料以及有机电致发光元件。In order to solve the above problems existing in the prior art, the present invention provides an indole derivative, an organic electroluminescent element, a display device and a lighting device. The indole derivative according to the present invention, as a raw material for organic electroluminescent element materials, can provide organic electroluminescent element materials and organic electroluminescent elements with reduced starting voltage, high luminous efficiency, and improved brightness.
为了实现上述目的，本发明采用如下技术方案：In order to achieve the above objects, the present invention adopts the following technical solutions:
一种吲哚衍生物，所述吲哚衍生物的结构如式(I)所示：
An indole derivative, the structure of the indole derivative is shown in formula (I):
An indole derivative, the structure of the indole derivative is shown in formula (I):
其中，W1和W2代表式(II)所示的基团；
Among them, W 1 and W 2 represent groups represented by formula (II);
Among them, W 1 and W 2 represent groups represented by formula (II);
Z各自独立地表示CR0或N；Z independently represents CR 0 or N;
相邻的两个“^”指示式(I)中相邻的基团W1和W2；Two adjacent "^" indicate adjacent groups W 1 and W 2 in formula (I);
R0、R1、R2、R3、R4、R5、R6、R7、R8、R9各自独立地选自由氢、氘、卤素、腈基、C1-C40的烷基、C3-C40的环烷基或带有支链的烷基、取代或未取代的C6-C60芳基、取代或未取代的C6-C60稠环芳基、取代或未取代的C6-C60芳胺基、取代或未取代的C2-C60杂芳基组成的群组，并且任意相邻的两个或多个基团可任选地接合或稠合形成另外的一个或多个取代或未取代的环，在所形成的环中含有或不含有一个或多个杂
原子N、P、B、O或S；R 0 , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 are each independently selected from hydrogen, deuterium, halogen, nitrile, and C 1 -C 40 alkane. group, C 3 -C 40 cycloalkyl or branched alkyl group, substituted or unsubstituted C 6 -C 60 aryl group, substituted or unsubstituted C 6 -C 60 fused ring aryl group, substituted or The group consisting of unsubstituted C 6 -C 60 arylamine groups, substituted or unsubstituted C 2 -C 60 heteroaryl groups, and any two or more adjacent groups may be optionally joined or fused Form one or more additional substituted or unsubstituted rings, with or without one or more heterocycles in the ring formed Atom N, P, B, O or S;
Ar1选自由取代或未取代的C6-C60芳基、取代或未取代的C2-C60杂芳基组成的群组；Ar 1 is selected from the group consisting of substituted or unsubstituted C 6 -C 60 aryl group and substituted or unsubstituted C 2 -C 60 heteroaryl group;
L选自由取代或未取代的C6-C60亚芳基、取代或未取代的C2-C60亚杂芳基组成的群组。L is selected from the group consisting of substituted or unsubstituted C 6 -C 60 arylene, substituted or unsubstituted C 2 -C 60 heteroarylene.
本发明意义上的芳基含有6～60个碳原子，在本发明意义上的杂芳基含有2～60个碳原子和至少一个杂原子，其条件是碳原子和杂原子的总和至少是5；所述杂原子优选选自N、O或S。此处的芳基或杂芳基涵盖单环基团和多环系统。多环可以具有两个碳为两个邻接环或称为“稠合的”共用的两个或更多个环，其中所述环中的至少一者是芳香族的，例如其它环可以是环烷基、环烯基、芳基、杂环和/或杂芳基。另外，多个芳基或杂芳基还可以由非芳族单元例如C、N、O或S原子连接，例如，和其中两个或更多个芳基被例如短的烷基连接的体系一样，诸如芴、9，9’-螺二芴、9，9-二芳基芴，三芳基胺、二芳基醚、二苯并呋喃或二苯并噻吩等。An aryl group in the sense of the present invention contains 6 to 60 carbon atoms, and a heteroaryl group in the sense of the present invention contains 2 to 60 carbon atoms and at least one heteroatom, provided that the sum of the carbon atoms and heteroatoms is at least 5 ; The heteroatom is preferably selected from N, O or S. Aryl or heteroaryl groups here encompass both monocyclic groups and polycyclic systems. A polycyclic ring may have two carbons common to two adjacent rings or referred to as "fused" to two or more rings, where at least one of the rings is aromatic, for example the other rings may be cyclic Alkyl, cycloalkenyl, aryl, heterocycle and/or heteroaryl. Additionally, multiple aryl or heteroaryl groups can also be linked by non-aromatic units such as C, N, O or S atoms, for example, as in systems in which two or more aryl groups are linked by, for example, short alkyl groups. , such as fluorene, 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamine, diaryl ether, dibenzofuran or dibenzothiophene, etc.
本发明中使用的烷基是指碳原子数从1至40的直链或支链的饱和烃去除一个氢原子而得到的一价官能团。作为其非限制性例子，有甲基、乙基、丙基、异丁基、仲丁基、戊基、异戊基、己基等。杂烷基是指烷基上的氢原子或-CH2-被至少一个杂原子取代，所述杂原子选自卤素、腈基、N、O、S或硅，作为非限制性的例子，有二氟甲基、三氟甲基、三氟乙基、五氟乙基、腈基、乙腈基、甲氧基甲基、甲氧基乙基、三甲基硅基、三异丙基硅基等。The alkyl group used in the present invention refers to a monovalent functional group obtained by removing one hydrogen atom from a linear or branched saturated hydrocarbon with a carbon number of 1 to 40. As non-limiting examples thereof, there are methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, isopentyl, hexyl and the like. Heteroalkyl means that the hydrogen atom or -CH2- on the alkyl group is replaced by at least one heteroatom, and the heteroatom is selected from halogen, nitrile, N, O, S or silicon. As non-limiting examples, there are two Fluoromethyl, trifluoromethyl, trifluoroethyl, pentafluoroethyl, nitrile, acetonitrile, methoxymethyl, methoxyethyl, trimethylsilyl, triisopropylsilyl, etc. .
本发明中使用的烯基是指从具有一个以上碳碳双键的碳原子数从2至40的直链或支链的不饱和烃去除一个氢原子而得到的一价官能团。作为其非限制性例子，有乙烯基、烯丙基、异丙烯基、2-丁烯基等。The alkenyl group used in the present invention refers to a monovalent functional group obtained by removing one hydrogen atom from a straight-chain or branched-chain unsaturated hydrocarbon having one or more carbon-carbon double bonds with a carbon number of 2 to 40. As non-limiting examples thereof, there are vinyl, allyl, isopropenyl, 2-butenyl and the like.
本发明中使用的炔基是指具有一个以上碳碳三键的碳原子数从2至40的直链或支链的不饱和烃去除一个氢原子而得到的一价官能团。作为其非限制性例子，有乙炔基、2-丙炔基等。The alkynyl group used in the present invention refers to a monovalent functional group obtained by removing one hydrogen atom from a straight-chain or branched-chain unsaturated hydrocarbon with more than one carbon-carbon triple bond and a carbon number of 2 to 40. As non-limiting examples thereof, there are ethynyl, 2-propynyl and the like.
一般来说，根据本发明的环烷基、环烯基是指碳原子数从3至40的单环或多环非芳族烃去除一个氢原子而得到的一价官能团。作为其非限制性例子，有环丙基、环丁基、环戊基、环己基、降冰片基、金刚烷基、环丁烯基、环戊烯基、环己烯基、环庚基、环庚烯基，其中一个或多个-CH2-基团可被上述基团代替；此外，一个或多个氢原子还可被氘原子、卤素原子或腈基代替。Generally speaking, cycloalkyl and cycloalkenyl according to the present invention refer to a monovalent functional group obtained by removing one hydrogen atom from a monocyclic or polycyclic non-aromatic hydrocarbon with a carbon number of 3 to 40. As non-limiting examples thereof, there are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, norbornyl, adamantyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptyl, Cycloheptenyl, in which one or more -CH 2 - groups can be replaced by the above-mentioned groups; in addition, one or more hydrogen atoms can also be replaced by deuterium atoms, halogen atoms or nitrile groups.
本发明中使用的杂环烷基是指原子核数从3至40的非芳香族烃去除一个氢原子而得到的一价官能团。此时，环中一个以上的碳、优选为1至3个碳被诸如N、O或S之类的杂原子取代。作为其非限制性例子，有四氢呋喃、四氢噻吩、吗啉、哌嗪等。The heterocycloalkyl group used in the present invention refers to a monovalent functional group obtained by removing one hydrogen atom from a non-aromatic hydrocarbon with a nuclear number of 3 to 40. In this case, more than one carbon in the ring, preferably 1 to 3 carbons, are substituted by heteroatoms such as N, O or S. As non-limiting examples thereof, there are tetrahydrofuran, tetrahydrothiophene, morpholine, piperazine and the like.
如本文所使用，“其组合”或“群组”表示适用清单的一或多个成员被组合以形成本领域普通技术人员能够从适用清单中设想的已知或化学稳定的布置。举例来说，烷基和氘可以组合形成部分或完全氘化的烷基；卤素和烷基可以组合形成卤代烷基取代基，例如三氟甲基等；并且卤素、烷基和芳基可以组合形成卤代芳烷基。As used herein, "combination" or "group" means that one or more members of an applicable list are combined to form a known or chemically stable arrangement that one of ordinary skill in the art would contemplate from the applicable list. For example, alkyl and deuterium can be combined to form partially or fully deuterated alkyl; halogen and alkyl can be combined to form haloalkyl substituents, such as trifluoromethyl, etc.; and halogen, alkyl, and aryl can be combined to form Haloaralkyl.
进一步地，所述吲哚衍生物选自由式I-1或式I-2组成的群组：
Further, the indole derivative is selected from the group consisting of formula I-1 or formula I-2:
Further, the indole derivative is selected from the group consisting of formula I-1 or formula I-2:
进一步地，所述Z各自独立地为CR0；Further, each of Z is independently CR 0 ;
Ar1选自取代或未取代的C2-C60杂芳基；Ar 1 is selected from substituted or unsubstituted C 2 -C 60 heteroaryl;
L选自由取代或未取代的C6-C60亚芳基、取代或未取代的C2-C60亚杂芳基组成的群组；L is selected from the group consisting of substituted or unsubstituted C 6 -C 60 arylene, substituted or unsubstituted C 2 -C 60 heteroarylene;
R0、R1、R2、R3、R4、R5、R6、R7、R8、R9各自独立地选自由以下基团组成的群组：氢、氘、取代或未取代的C6-C60芳基或取代或未取代的C2-C60杂芳基。R 0 , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 are each independently selected from the group consisting of: hydrogen, deuterium, substituted or unsubstituted C 6 -C 60 aryl or substituted or unsubstituted C 2 -C 60 heteroaryl.
进一步地，所述杂芳基选自由以下II-1～II-17所示基团组成的群组：
Further, the heteroaryl group is selected from the group consisting of the following groups shown in II-1 to II-17:
Further, the heteroaryl group is selected from the group consisting of the following groups shown in II-1 to II-17:
其中，in,
Z1、Z2各自独立地选自由氢、氘、卤素、羟基、腈基、硝基、氨基、脒基、肼基、腙基、羧基或其羧酸盐、磺酸基或其磺酸盐、磷酸基或其磷酸盐、C1-C40烷基、C2-C40烯基、C2-C40炔基、C1-C40烷氧基、C3-C40环烷烃基、C3-C40环烯烃基、取代或未取代的C6-C60芳基、取代或未取代的C6-C60芳氧基、取代或未取代的C6-C60芳硫醚基、或者取代或未取代的C2-C60杂环芳基组成的群组；Z 1 and Z 2 are each independently selected from hydrogen, deuterium, halogen, hydroxyl, nitrile group, nitro group, amino group, amidine group, hydrazine group, hydrazone group, carboxyl group or its carboxylate, sulfonic acid group or its sulfonate , phosphate group or its phosphate, C 1 -C 40 alkyl group, C 2 -C 40 alkenyl group, C 2 -C 40 alkynyl group, C 1 -C 40 alkoxy group, C 3 -C 40 cycloalkyl group, C 3 -C 40 cycloalkenyl group, substituted or unsubstituted C 6 -C 60 aryl group, substituted or unsubstituted C 6 -C 60 aryloxy group, substituted or unsubstituted C 6 -C 60 aryl sulfide group , or a group consisting of substituted or unsubstituted C 2 -C 60 heterocyclic aryl groups;
x1表示1-4的整数；x2表示1-3的整数；x3表示1或2；x4表示1-6的整数；x5表示1-5的整数；x1 represents an integer from 1 to 4; x2 represents an integer from 1 to 3; x3 represents 1 or 2; x4 represents an integer from 1 to 6; x5 represents an integer from 1 to 5;
T1表示O、S、CR’R”或NAr’；T 1 means O, S, CR'R" or NAr';
R’、R”各自独立地选自由氢、氘、C1～C40的烷基、C1～C40的杂烷基、取代或未取代的C6-C60芳基、取代或未取代的C6-C60芳胺基、或者取代或未取代的C2-C60杂环芳基组成的群组，R’和R”可任选地接合或稠合形成另外的一个多个取代或未取代的环，在所形成的环中含有或不含有一个或多个杂原子N、P、B、O或S；优选地，R’、R”为甲基、苯基或芴基；R', R" are each independently selected from hydrogen, deuterium, C 1 to C 40 alkyl group, C 1 to C 40 heteroalkyl group, substituted or unsubstituted C 6 to C 60 aryl group, substituted or unsubstituted A group consisting of C 6 -C 60 arylamine groups, or substituted or unsubstituted C 2 -C 60 heterocyclic aryl groups, R' and R" can optionally be joined or fused to form another multiple substituted Or an unsubstituted ring, containing or not containing one or more heteroatoms N, P, B, O or S in the formed ring; preferably, R', R" is methyl, phenyl or fluorenyl;
Ar’选自由C1～C40的烷基、C1～C40的杂烷基、C3～C40的环烷基、取代或未取代的C6-C60芳基、取代或未取代的C6-C60稠环芳基、取代或未取代的C6-C60芳胺基、或者取代或未取代的C2-C60杂环芳基组成的群组；优选地，Ar’为甲基、乙基、苯基、联苯基或萘基；Ar' is selected from C 1 to C 40 alkyl, C 1 to C 40 heteroalkyl, C 3 to C 40 cycloalkyl, substituted or unsubstituted C 6 -C 60 aryl, substituted or unsubstituted A group consisting of a C 6 -C 60 fused ring aryl group, a substituted or unsubstituted C 6 -C 60 arylamine group, or a substituted or unsubstituted C 2 -C 60 heterocyclic aryl group; preferably, Ar' is methyl, ethyl, phenyl, biphenyl or naphthyl;
表示取代基与杂芳基的连接键。 Indicates the bond between the substituent and the heteroaryl group.
进一步地，所述Ar1选自由以下III-1～III-18所示基团组成的群组：
Further, the Ar 1 is selected from the group consisting of the following groups III-1 to III-18:
Further, the Ar 1 is selected from the group consisting of the following groups III-1 to III-18:
其中，T2选自O或S；Among them, T 2 is selected from O or S;
R10、R11各自独立地选自由氢、氘、取代或未取代的C6～C60芳基、取代或未取代的C2～C60杂芳基组成的群组；R 10 and R 11 are each independently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted C 6 to C 60 aryl groups, and substituted or unsubstituted C 2 to C 60 heteroaryl groups;
R12选自由氢、氘、C1～C40的烷基、取代或未取代的C6-C60芳基、或者取代或未取代的C2-C60杂芳基组成的群组；R12为一个或多个至饱和取代；R 12 is selected from the group consisting of hydrogen, deuterium, C 1 to C 40 alkyl, substituted or unsubstituted C 6 -C 60 aryl, or substituted or unsubstituted C 2 -C 60 heteroaryl; R 12 is one or more saturated substitutions;
*-表示Ar1取代基与L的连接键。*-Indicates the bond between Ar 1 substituent and L.
根据本发明的实施例，所述R10、R11各自独立地选自由苯基、联苯基、三联苯基、萘基、菲基、三亚苯基、萘取代的苯基、菲取代的苯基、二苯并呋喃基、二苯并噻吩基、咔唑基、二苯并呋喃取代的苯基、二苯并噻吩取代的苯基、苯基取代的咔唑基、萘基取代的咔唑基、联苯取代的咔唑基、9-苯基咔唑基、苯并萘并呋喃基、苯并萘并噻吩基或苯基取代的苯并咔唑基组成的群组。According to embodiments of the present invention, R 10 and R 11 are each independently selected from phenyl, biphenyl, terphenyl, naphthyl, phenanthrenyl, triphenylene, naphthalene-substituted phenyl, phenanthrene-substituted phenyl base, dibenzofuranyl, dibenzothienyl, carbazolyl, dibenzofuran-substituted phenyl, dibenzothiophene-substituted phenyl, phenyl-substituted carbazolyl, naphthyl-substituted carbazole group consisting of a biphenyl-substituted carbazolyl group, a 9-phenylcarbazolyl group, a benzonaphthofuranyl group, a benzonaphthothienyl group or a phenyl-substituted benzocarbazolyl group.
根据本发明的实施例，R12为氢或氘。According to an embodiment of the invention, R 12 is hydrogen or deuterium.
进一步地，所述L选自单键、亚苯基、亚吡啶基或萘二基。Further, the L is selected from a single bond, a phenylene group, a pyridinyl group or a naphthalenediyl group.
根据本发明的一个实施例，所述R0、R1、R2、R3、R4、R5、R6、R7、R8和R9都为氢。According to an embodiment of the present invention, the R 0 , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are all hydrogen.
进一步的，所述的咔唑衍生物为以下N313～N582所示结构中的一种：
Further, the carbazole derivative is one of the following structures shown in N313~N582:
Further, the carbazole derivative is one of the following structures shown in N313~N582:
其中，*-T3-*各自独立地选自*-O-*、*-S-*或下述结构中的一种：
Among them, *-T 3 -* is each independently selected from *-O-*, *-S-* or one of the following structures:
Among them, *-T 3 -* is each independently selected from *-O-*, *-S-* or one of the following structures:
*-和-*表示连接键。*- and -* represent connection keys.
另一方面，本发明提供了一种式(I)化合物的制备方法，以如下方案1、方案2为例：On the other hand, the present invention provides a method for preparing the compound of formula (I), taking the following scheme 1 and scheme 2 as examples:
方案1：
plan 1:
plan 1:
方案2：
Scenario 2:
Scenario 2:
在方案1、方案2中，所用符号如式(I)中所定义，并且X为Cl、Br、I或OTf；In scheme 1 and scheme 2, the symbols used are as defined in formula (I), and X is Cl, Br, I or OTf;
具体地，式(I)的化合物是由具有母核结构的化合物C1或C2和含有受体取代基的化合物D通过钯催化或碱催化偶联反应制备。Specifically, the compound of formula (I) is prepared by a palladium-catalyzed or base-catalyzed coupling reaction from compound C1 or C2 having a parent core structure and compound D containing an acceptor substituent.
作为可用于钯催化偶联反应的钯催化剂可选自：Pd(P-tBu3)2、Pd(PPh3)4、Pd2(dba)3、Pd2(dba)3CHCl3、PdCl2(PPh3)2、PdCl2(CH3CN)2、Pd(OAc)2、Pd(acac)2、Pd/C、PdCl2、[Pd(allyl)Cl]2等任意一种，或使用两种或更多种的混合物。As a palladium catalyst that can be used for palladium-catalyzed coupling reaction, it can be selected from: Pd(P- t Bu 3 ) 2 , Pd(PPh 3 ) 4 , Pd 2 (dba) 3 , Pd 2 (dba) 3 CHCl 3 , PdCl 2 (PPh 3 ) 2 , PdCl 2 (CH 3 CN) 2 , Pd(OAc) 2 , Pd(acac) 2 , Pd/C, PdCl 2 , [Pd(allyl)Cl] 2, etc., or use two mixture of one or more species.
此外，钯催化的偶联反应或碱催化的偶联反应使用的碱可选自：叔丁醇钠、叔丁醇钾、氢化钠、氢化锂、叔戊醇钠、乙醇钠、甲醇钠、碳酸钠、碳酸钾、碳酸铯、锂、氢化钾、三乙胺、氟化铯等，以及其中一种或两种或更多种的混合物。In addition, the base used in the palladium-catalyzed coupling reaction or the base-catalyzed coupling reaction can be selected from: sodium tert-butoxide, potassium tert-butoxide, sodium hydride, lithium hydride, sodium tert-amyloxide, sodium ethoxide, sodium methoxide, carbonic acid Sodium, potassium carbonate, cesium carbonate, lithium, potassium hydride, triethylamine, cesium fluoride, etc., as well as one or a mixture of two or more thereof.
偶联反应可以在有机溶剂中进行，其中有机溶剂可选自：乙醚、四氢呋喃、2-甲基四氢呋喃、1，4-二氧六环、乙二醇乙醚、乙二醇二乙醚、乙二醇甲醚、二甘醇二乙醚、或苯甲醚等醚类溶剂、苯、甲苯、二甲苯等芳烃类剂、氯苯、二氯苯、N，N-二甲基甲酰胺、N，N-二甲基乙酰胺、N-甲基吡咯烷酮、二甲基亚砜、环丁砜等，可以使用一种或两种以上的混合物。The coupling reaction can be carried out in an organic solvent, wherein the organic solvent can be selected from: diethyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-dioxane, ethylene glycol ethyl ether, ethylene glycol diethyl ether, ethylene glycol Ether solvents such as methyl ether, diglyme, or anisole, aromatic hydrocarbon agents such as benzene, toluene, and xylene, chlorobenzene, dichlorobenzene, N,N-dimethylformamide, N,N- One type or a mixture of two or more types of dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide, sulfolane, etc. can be used.
此外，化合物D可使用常规有机反应制备，或者可以从商业途径获得。Furthermore, Compound D can be prepared using conventional organic reactions or can be obtained from commercial sources.
另外，本发明提供一种有机电致发光元件，包括第一电极、第二电极、封盖层和置于第一电极和第二电极之间的至少一层有机层，所述的有机层或封盖层中至少一层包括所述的吲哚衍生物。In addition, the present invention provides an organic electroluminescent element, including a first electrode, a second electrode, a capping layer and at least one organic layer placed between the first electrode and the second electrode, the organic layer or At least one layer of the capping layer includes the indole derivative.
所述有机电致发光元件包含阴极、阳极和至少一个发光层。除了这些层之外，它还可以包含其它的层，例如在每种情况下，包含一个或多个空穴注入层、空穴传输层、空穴阻挡层、电子传输层、电子注入层、激子阻挡层、电子阻挡层和/或电荷产生层。具有例如激子阻挡功能的中间层同样可引入两个发光层之间。然而，应当指出，这些层中的每个并非必须都存在。此处所述有机电致发光装置可包含一个发光层，或者它可包含多个发光层。即，将能够发光的多种发光化合物用于所述发光层中。特别优选具有三个发光层的体系，其中所述三个层可显示蓝色、绿色和红色发光。如果存在多于一个的发光层，则根据本发明，这些层中的至少一个层包含本发明的吲哚衍生物。The organic electroluminescent element includes a cathode, an anode and at least one light-emitting layer. In addition to these layers, it may contain further layers, for example in each case one or more hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, excitation layers, etc. sub-blocking layer, electron blocking layer and/or charge generating layer. An intermediate layer having, for example, an exciton blocking function can also be introduced between the two luminescent layers. However, it should be noted that each of these layers does not necessarily have to be present. The organic electroluminescent device described herein may include one light emitting layer, or it may include multiple light emitting layers. That is, a plurality of light-emitting compounds capable of emitting light are used in the light-emitting layer. Particularly preferred are systems with three luminescent layers, wherein the three layers can exhibit blue, green and red luminescence. If more than one luminescent layer is present, according to the invention at least one of these layers contains an indole derivative according to the invention.
在根据本发明的有机电致发光元件的其它层中，特别是在发光层和薄膜封装层中，所有材料可以按照根据现有技术通常所使用的方式来使用。本领域普通技术人员因此将能够在不付出创造性劳动的情况下与根据本发明的发光层组合使用关于有机电致发光元件所知的所有材料。
In the other layers of the organic electroluminescent element according to the invention, in particular in the light-emitting layer and the thin film encapsulation layer, all materials can be used in the manner generally used according to the prior art. A person skilled in the art will therefore be able to use, without inventive effort, all materials known for organic electroluminescent components in combination with the luminescent layer according to the invention.
此外优选如下的有机电致发光元件，借助于升华方法施加一个或多个层，其中在真空升华装置中在低于10-5Pa、优选低于10-6Pa的初压下通过气相沉积来施加所述材料。然而，所述初压还可能甚至更低，例如低于10-7Pa。Furthermore, organic electroluminescent components are preferred in which one or more layers are applied by means of a sublimation method, wherein the layer is deposited by vapor deposition in a vacuum sublimation device at an initial pressure of less than 10 -5 Pa, preferably less than 10 -6 Pa. Apply the material. However, the initial pressure may also be even lower, for example below 10 -7 Pa.
同样优选如下的有机电致发光元件，借助于有机气相沉积方法或借助于载气升华来施加一个或多个层，其中，在10-5Pa至1Pa之间的压力下施加所述材料。该方法的特别的例子是有机蒸汽喷印方法，其中所述材料通过喷嘴直接施加，并且因此是结构化的。Also preferred are organic electroluminescent elements in which one or more layers are applied by means of an organic vapor deposition method or by means of carrier gas sublimation, wherein the material is applied at a pressure of between 10 −5 Pa and 1 Pa. A particular example of this method is the organic vapor jet printing method, in which the material is applied directly through a nozzle and is therefore structured.
此外优选如下的有机电致发光元件，从溶液中，例如通过旋涂，或借助于任何所希望的印刷方法例如丝网印刷、柔性版印刷、平版印刷、光引发热成像、热转印、喷墨印刷或喷嘴印刷，来产生一个或多个层。可溶性化合物，例如通过适当的取代式(I)所示的化合物获得可溶性化合物。这些方法也特别适于低聚物、树枝状大分子和聚合物。此外可行的是混合方法，其中例如从溶液中施加一个或多个层并且通过气相沉积施加一个或多个另外的层。Furthermore, preference is given to organic electroluminescent elements produced from solution, for example by spin coating, or by means of any desired printing method, such as screen printing, flexographic printing, lithography, photothermography, thermal transfer printing, spray printing, etc. Ink printing or nozzle printing to produce one or more layers. Soluble compounds can be obtained, for example, by appropriately substituting compounds represented by formula (I). These methods are also particularly suitable for oligomers, dendrimers and polymers. Furthermore, hybrid methods are possible, in which one or more layers are applied, for example, from solution and one or more further layers are applied by vapor deposition.
进一步地，所述有机层还包括选自电子注入层、电子输送层、空穴阻挡层、电子阻挡层、空穴输送层、空穴注入层、发光层、光折射层的一种以上。Further, the organic layer further includes at least one selected from the group consisting of an electron injection layer, an electron transport layer, a hole blocking layer, an electron blocking layer, a hole transport layer, a hole injection layer, a light emitting layer, and a photorefractive layer.
本发明的有机电致发光元件既可以是顶发射光元件，又可以是底发射光元件。本发明的有机电致发光元件的结构和制备方法没有限定。采用本发明的化合物制得的有机电致发光元件可降低启动电压、提高发光效率和亮度。The organic electroluminescent element of the present invention can be either a top-emitting light-emitting element or a bottom-emitting light-emitting element. The structure and preparation method of the organic electroluminescent element of the present invention are not limited. The organic electroluminescent element prepared by using the compound of the present invention can reduce the starting voltage and improve the luminous efficiency and brightness.
一种显示装置，包括所述的有机电致发光元件。A display device includes the organic electroluminescent element.
一种照明装置，包括所述的有机电致发光元件。A lighting device includes the organic electroluminescent element.
本发明的有机元件用材料含有本发明的吲哚衍生物。有机元件用材料可以单独使用本发明的化合物构成，也可以同时含有其他化合物。The material for organic devices of the present invention contains the indole derivative of the present invention. The material for organic elements may be composed of the compound of the present invention alone or may contain other compounds.
本发明的有机电致发光元件用材料中所含有的本发明的吲哚衍生物可以用作主体材料。此时，本发明的有机电致发光元件用材料中可以含有作为掺杂材料的其他化合物。The indole derivative of the present invention contained in the material for organic electroluminescent elements of the present invention can be used as a host material. In this case, the material for organic electroluminescence elements of the present invention may contain other compounds as doping materials.
本发明的有机电致发光元件用材料还可以作为空穴传输层、增强层、发光层、电子传输层、电荷产生层、电子阻挡层、封盖层或光折射层用材料。The material for organic electroluminescent elements of the present invention can also be used as a material for a hole transport layer, an enhancement layer, a light emitting layer, an electron transport layer, a charge generation layer, an electron blocking layer, a capping layer or a photorefractive layer.
本发明还涉及包含至少一种式(I)化合物或上述优选实施方式和至少一种其它化合物的混合物。如果将根据本发明的化合物用作基质材料，则其它化合物可以是荧光或磷光发光体。于是该混合物还可以另外包含其它材料作为附加基质材料。本发明还涉及本发明的化合物在电子元件中的用途。优选地，如上下文提及的，将根据本发明的化合物用于电子传输层中或用作发光层中的基质材料。根据本发明的化合物和可由此获得的电子元件、特别是有机电致发光元件与现有技术的区别在于以下令人惊讶的优势中的一种或多种：The invention also relates to mixtures comprising at least one compound of formula (I) or the preferred embodiments described above and at least one further compound. If the compounds according to the invention are used as matrix materials, the other compounds can be fluorescent or phosphorescent emitters. The mixture may then additionally contain other materials as additional matrix materials. The invention also relates to the use of the compounds of the invention in electronic components. Preferably, as mentioned above and below, the compounds according to the invention are used in electron transport layers or as matrix materials in light-emitting layers. The compounds according to the invention and the electronic components obtainable therefrom, in particular organic electroluminescent components, differ from the prior art by one or more of the following surprising advantages:
1.与使用常规化合物获得的电子元件相比，使用本发明的化合物可获得的电子元件表现出非常高的稳定性和非常长的寿命。1. Compared with electronic components obtained using conventional compounds, electronic components obtainable using the compounds of the present invention exhibit very high stability and very long life.
2.使用本发明的化合物可获得的电子元件表现出高的效率，特别是高的发光效率和高的外量子效率。2. The electronic components obtainable using the compounds of the present invention exhibit high efficiency, especially high luminous efficiency and high external quantum efficiency.
3.本发明的化合物提供低工作电压。3. The compounds of the present invention provide low operating voltage.
4.可以使用常规方法处理根据本发明的化合物，从而也能够实现成本优势。4. The compounds according to the invention can be processed using conventional methods, so that cost advantages can also be achieved.
5.使用本发明的化合物可获得的薄膜表现出优异的品质，特别是在薄膜的均匀性方面更是如此。5. The films obtainable using the compounds of the present invention exhibit excellent qualities, especially in terms of film uniformity.
6.可以使用常规方法以非常快速且容易的方式产生本发明的化合物，从而也能够实现成本优势。6. The compounds of the invention can be produced in a very fast and easy manner using conventional methods, so that cost advantages can also be achieved.
上文提及的这些优势并未伴随其它电子性质的削弱。These advantages mentioned above are not accompanied by a decrease in other electronic properties.
应该指出，本发明中所述的实施方式的变化落入本发明的范围内。本发明中公开的每个特征除非被明确排除，否则可被具有相同、等效或类似目的的替代特征代替。因此，除非另外说明，否则本发明中公开的每个特征均应被视为类属系列的实例或者等效或类似特征。It should be noted that variations of the embodiments described in this invention fall within the scope of this invention. Each feature disclosed in this invention, unless expressly excluded, may be replaced by alternative features serving the same, equivalent or similar purpose. Therefore, unless stated otherwise, each feature disclosed in this invention should be considered an example of a generic series or an equivalent or similar feature.
本发明的所有特征可以以任何方式彼此组合，除非特定特征和/或步骤是互斥的。这特别适用于本发明的优选特征。同样，非必须组合的特征可以单独(且不组合)使用。此外应该指出，许多特征，特别是本发明的优选实施方式的特征本身是创造性的，并且不应仅视为本发明实施方式的一部分。对于这些特征，除当前要求保护的每个发明以外或作为其替代，可以寻求独立的保护。All features of the invention may be combined with each other in any way, unless specific features and/or steps are mutually exclusive. This applies particularly to preferred features of the invention. Likewise, features that do not necessarily need to be combined can be used individually (and not in combination). Furthermore, it should be pointed out that many features, in particular features of the preferred embodiments of the invention, are inventive in themselves and should not be regarded as merely part of the embodiments of the invention. For these features, independent protection may be sought in addition to or as an alternative to each invention currently claimed.
对本发明中公开的技术动作的教导可以被提取出并且与其它实施例组合。本发明通过以下实施例更加详细地解释，但不希望由此限制本发明。基于所述描述，本领域技术人员将能够在所公开的整个范围内执行本发明，并且不付出创造性劳动就能够制备本发明的其它化合物并将其用于电子元件中，或使用本发明的方法。The teachings of the technical acts disclosed in the present invention can be extracted and combined with other embodiments. The invention is explained in more detail by the following examples, without wishing to limit the invention thereby. Based on the description, a person skilled in the art will be able to carry out the invention within the entire scope disclosed and to prepare other compounds of the invention and use them in electronic components or to use the method of the invention without exerting creative effort .
为了更清楚地说明本发明实施例或现有技术中的技术方案，下面将对实施例或现有技术描述中所需要使用的附图作简单地介绍，显而易见地，下面描述中的附图仅仅是本发明的一些实施例，对于本领域普通
技术人员来讲，在不付出创造性劳动的前提下，还可以根据这些附图获得其他的附图。In order to explain the embodiments of the present invention or the technical solutions in the prior art more clearly, the drawings needed to be used in the description of the embodiments or the prior art will be briefly introduced below. Obviously, the drawings in the following description are only are some embodiments of the present invention. For ordinary people in the art For technical personnel, other drawings can also be obtained based on these drawings without exerting creative work.
图1展示有机发光装置100示意图。图示不一定按比例绘制。装置100可包含衬底101、阳极102、空穴注入层103、空穴传输层104、电子阻挡层105、发光层106、空穴阻挡层107、电子传输层108、电子注入层109、阴极110以及封盖层(CPL)111。装置100可通过依序沉积所描述的层来制造。FIG. 1 shows a schematic diagram of an organic light-emitting device 100. Illustrations are not necessarily to scale. Device 100 may include substrate 101, anode 102, hole injection layer 103, hole transport layer 104, electron blocking layer 105, light emitting layer 106, hole blocking layer 107, electron transport layer 108, electron injection layer 109, cathode 110 and capping layer (CPL) 111. Device 100 may be fabricated by sequentially depositing the described layers.
图2展示两个发光层的有机发光装置200示意图。所述装置包含衬底201、阳极202、空穴注入203、空穴传输层204、第一发光层205、电子传输层206、、电荷产生层207、空穴注入层208、空穴传输层209、第二发光层210、电子传输层211、电子注入层212以及阴极213。可通过依序沉积所描述的层来制备装置200。因为最常见的OLED装置具有一个发光层，而装置200具有第一发光层和第二发光层，第一发光层和第二发光层的发光峰形可以是重叠的或交叉重叠的或非重叠的。在装置200的对应层中，可使用与关于装置100所描述的材料类似的材料。图2提供可如何从装置100的结构增加一些层的一个实例。FIG. 2 shows a schematic diagram of an organic light-emitting device 200 with two light-emitting layers. The device includes a substrate 201, an anode 202, a hole injection layer 203, a hole transport layer 204, a first light-emitting layer 205, an electron transport layer 206, a charge generation layer 207, a hole injection layer 208, and a hole transport layer 209. , the second light-emitting layer 210, the electron transport layer 211, the electron injection layer 212 and the cathode 213. Device 200 may be prepared by sequentially depositing the described layers. Because the most common OLED device has one luminescent layer, and the device 200 has a first luminescent layer and a second luminescent layer, the luminescence peak shapes of the first luminescent layer and the second luminescent layer may be overlapping or cross-overlapping or non-overlapping. . In corresponding layers of device 200, materials similar to those described with respect to device 100 may be used. Figure 2 provides an example of how some layers may be added from the structure of device 100.
为使本发明的目的、技术方案和优点更加清楚，下面将对本发明的技术方案进行详细的描述。显然，所描述的实施例仅仅是本发明一部分实施例，而不是全部的实施例。基于本发明中的实施例，本领域普通技术人员在没有做出创造性劳动的前提下所得到的所有其它实施方式，都属于本发明所保护的范围。In order to make the purpose, technical solutions and advantages of the present invention clearer, the technical solutions of the present invention will be described in detail below. Obviously, the described embodiments are only some of the embodiments of the present invention, but not all of the embodiments. Based on the embodiments of the present invention, all other implementations obtained by those of ordinary skill in the art without any creative work fall within the scope of protection of the present invention.
以下实施例中OLED材料及元件进行性能测试的测试仪器及方法如下：The testing instruments and methods for performance testing of OLED materials and components in the following examples are as follows:
OLED元件性能检测条件：OLED component performance testing conditions:
亮度和色度坐标：使用光谱扫描仪PhotoResearch PR-715测试；Luminance and chromaticity coordinates: tested using spectral scanner PhotoResearch PR-715;
电流密度和起亮电压：使用数字源表Keithley 2420测试；Current density and lighting voltage: tested using digital source meter Keithley 2420;
功率效率：使用NEWPORT 1931-C测试；Power efficiency: tested using NEWPORT 1931-C;
寿命测试：使用LTS-1004AC寿命测试装置。Life test: Use LTS-1004AC life test device.
实施例1Example 1
化合物N315的制备方法，包括如下步骤：The preparation method of compound N315 includes the following steps:
第一步：中间体Int-1的制备
Step 1: Preparation of intermediate Int-1
Step 1: Preparation of intermediate Int-1
20.0mmol的1-溴-11H-苯并[a]咔唑(CAS：2126733-20-6)、22.0mmol的邻胺基苯乙胺、2.0mmol的碘化亚铜、0.2mmol的醋酸钯和0.4mmol的三苯基磷，再加入40mL的THF和20mL的三乙胺，在氮气保护下，升温至回流搅拌反应8小时，降到室温，减压浓缩干，再用硅胶柱分离纯化，得黄色固体Int-1，收率：85％。20.0mmol of 1-bromo-11H-benzo[a]carbazole (CAS: 2126733-20-6), 22.0mmol of o-aminophenylethylamine, 2.0mmol of copper iodide, 0.2mmol of palladium acetate and 0.4 mmol of triphenylphosphonate, then add 40 mL of THF and 20 mL of triethylamine, under nitrogen protection, raise the temperature to reflux and stir for 8 hours, then cool to room temperature, concentrate to dryness under reduced pressure, and then separate and purify with a silica gel column to obtain Yellow solid Int-1, yield: 85%.
第二步：中间体Int-2的制备
Step 2: Preparation of intermediate Int-2
Step 2: Preparation of intermediate Int-2
在氮气保护下，20.0mmol的Int-1、50.0mmol的溴化铜、40.0mmol的碳酸铯和40mL的DMSO，于室温搅拌反应3小时，升温至110℃搅拌反应12小时，降到室温，将反应液倒入150mL的水中，过滤，滤饼用水洗、乙醇洗，过硅胶短柱，洗脱液减压浓缩干，得黄色固体Int-2，收率：92％。Under nitrogen protection, 20.0 mmol of Int-1, 50.0 mmol of copper bromide, 40.0 mmol of cesium carbonate and 40 mL of DMSO were stirred and reacted at room temperature for 3 hours. The temperature was raised to 110°C and stirred for 12 hours. Then it was lowered to room temperature. The reaction solution was poured into 150 mL of water, filtered, the filter cake was washed with water and ethanol, and passed through a short silica gel column. The eluate was concentrated to dryness under reduced pressure to obtain yellow solid Int-2, yield: 92%.
第三步：化合物C1的制备
Step 3: Preparation of Compound C1
Step 3: Preparation of Compound C1
在氮气保护下，20.0mmol的Int-2、60.0mmol的叔丁醇钾和40mL的DMSO，于室温搅拌反应3小时，将反应液倒入150mL的冰水中，用稀盐酸酸化，过滤，滤饼用水洗、乙醇洗，过硅胶短柱，洗脱液减压浓缩干，得黄色固体C1，收率：95％。Under nitrogen protection, 20.0 mmol of Int-2, 60.0 mmol of potassium tert-butoxide and 40 mL of DMSO were stirred at room temperature for 3 hours. Pour the reaction solution into 150 mL of ice water, acidify with dilute hydrochloric acid, filter, and filter the cake. Wash with water and ethanol, pass through a short silica gel column, and concentrate the eluent to dryness under reduced pressure to obtain yellow solid C1, yield: 95%.
第四步：化合物N315的制备
Step 4: Preparation of compound N315
Step 4: Preparation of compound N315
10.0mmol化合物C1溶解于50mL干燥的DMF中，在氮气保护下，用冰水浴降温至0℃，分批加入12.0mmol的65％氢化钠固体，搅拌反应1小时，加入12.0mmol的2-氯-4-联苯基喹唑啉，升温至45℃搅拌反应12小时，将反应液倒入250mL冰水中，过滤，滤饼用水洗、乙醇洗，用硅胶柱分离纯化，得到化合物N315，黄色固体，收率：88％，MS(MALDI-TOF)：m/z 611.2245[M+H]+；1HNMR(δ、CDCl3)：8.87～8.82(1H，m)；8.38～8.31(5H，m)；8.04～7.92(3H，m)；7.90～7.84(3H，m)；7.73～7.62(5H，m)；7.53～7.40(7H，m)；7.34～7.29(2H，m)。Dissolve 10.0 mmol of compound C1 in 50 mL of dry DMF. Under nitrogen protection, use an ice water bath to cool down to 0°C. Add 12.0 mmol of 65% sodium hydride solid in batches and stir for 1 hour. Add 12.0 mmol of 2-chloro- 4-Biphenylquinazoline, raise the temperature to 45°C and stir for 12 hours. Pour the reaction solution into 250 mL of ice water, filter, wash the filter cake with water and ethanol, and separate and purify with a silica gel column to obtain compound N315, a yellow solid. Yield: 88%, MS (MALDI-TOF): m/z 611.2245[M+H] + ; 1 HNMR (δ, CDCl 3 ): 8.87～8.82 (1H, m); 8.38～8.31 (5H, m) ; 8.04～7.92 (3H, m); 7.90～7.84 (3H, m); 7.73～7.62 (5H, m); 7.53～7.40 (7H, m); 7.34～7.29 (2H, m).
参照上述类似的合成方法，制备以下化合物：
Referring to the above-mentioned similar synthetic methods, prepare the following compounds:
Referring to the above-mentioned similar synthetic methods, prepare the following compounds:
实施例2Example 2
化合物N430的制备，包括如下步骤：The preparation of compound N430 includes the following steps:
第一步：中间体Int-3的制备
Step 1: Preparation of intermediate Int-3
Step 1: Preparation of intermediate Int-3
在氮气保护下，20.0mmol的1-溴-11H-苯并[a]咔唑(CAS：2126733-20-6)、22.0mmol的2-溴-1-Tos-吲哚、2.0mmol的碘化亚铜、24.0mmol的碳酸铯，再加入40mL的1-甲基吡咯烷酮，升温至回流搅拌反应12小时，降到室温，加入120mL的水，用乙酸乙酯萃取，有机相干燥，过滤，滤液减压浓缩干，再用硅胶柱分离纯化，得黄色固体Int-3，收率：86％。Under nitrogen protection, 20.0mmol of 1-bromo-11H-benzo[a]carbazole (CAS: 2126733-20-6), 22.0mmol of 2-bromo-1-Tos-indole, 2.0mmol of iodide Cuprous, 24.0 mmol of cesium carbonate, then add 40 mL of 1-methylpyrrolidone, heat to reflux and stir for 12 hours, cool to room temperature, add 120 mL of water, extract with ethyl acetate, dry the organic phase, filter, and reduce the filtrate Concentrate to dryness, and then separate and purify using a silica gel column to obtain yellow solid Int-3, yield: 86%.
第二步：中间体Int-4的制备
Step 2: Preparation of intermediate Int-4
Step 2: Preparation of intermediate Int-4
在氮气保护下，15.0mmol化合物Int-3溶解于50mL干燥的甲苯中，加入22.5mmol的叔丁醇钠、0.1mmol的醋酸钯和0.2mmol的XPhos，升温至100℃，搅拌反应15小时，冷却到室温，加入50mL水稀释，用二氯甲烷萃取，收集有机相，干燥，过滤，滤液减压浓缩干，用硅胶柱分离纯化，得到化合物Int-4，黄色固体，收率：88％。
Under nitrogen protection, 15.0 mmol of compound Int-3 was dissolved in 50 mL of dry toluene, 22.5 mmol of sodium tert-butoxide, 0.1 mmol of palladium acetate and 0.2 mmol of XPhos were added, the temperature was raised to 100°C, the reaction was stirred for 15 hours, and cooled to room temperature, add 50 mL of water to dilute, extract with dichloromethane, collect the organic phase, dry, filter, and concentrate the filtrate to dryness under reduced pressure, and separate and purify with a silica gel column to obtain compound Int-4, a yellow solid, yield: 88%.
第三步：化合物C2的制备
Step 3: Preparation of Compound C2
Step 3: Preparation of Compound C2
参照实施例1第三步的合成方法，仅将实施例1第三步的Int-2替换为Int-4，制备得到化合物C2，黄色固体，收率：90％。Referring to the synthesis method in the third step of Example 1, only replacing Int-2 in the third step of Example 1 with Int-4, compound C2 was prepared as a yellow solid with a yield of 90%.
第四步：化合物N430的制备
Step 4: Preparation of compound N430
Step 4: Preparation of compound N430
10.0mmol化合物C2溶解于50mL干燥的DMF中，在氮气保护下，用冰水浴降温至0℃，分批加入12.0mmol的65％氢化钠固体，搅拌反应1小时，加入12.0mmol的2-氯-4-苯基喹唑啉，升至室温搅拌反应12小时，将反应液倒入250mL冰水中，过滤，滤饼用水洗、乙醇洗，用硅胶柱分离纯化，得到化合物N430，黄色固体，收率：82％，MS(MALDI-TOF)：m/z 535.1936[M+H]+；1HNMR(δ、CDCl3)：8.54～8.46(3H，m)；8.36(1H，s)；8.15～8.06(3H，m)；7.94～7.91(1H，m)；7.86～7.73(5H，m)；7.70～7.66(1H，m)；7.62～7.49(6H，m)；7.47～7.43(1H，m)；7.38～7.34(1H，m)。Dissolve 10.0 mmol of compound C2 in 50 mL of dry DMF. Under nitrogen protection, use an ice water bath to cool down to 0°C. Add 12.0 mmol of 65% sodium hydride solid in batches and stir for 1 hour. Add 12.0 mmol of 2-chloro- 4-Phenylquinazoline, raise to room temperature and stir for 12 hours, pour the reaction solution into 250 mL ice water, filter, wash the filter cake with water and ethanol, and separate and purify with a silica gel column to obtain compound N430, a yellow solid, yield : 82%, MS (MALDI-TOF): m/z 535.1936 [M+H] + ; 1 HNMR (δ, CDCl 3 ): 8.54～8.46 (3H, m); 8.36 (1H, s); 8.15～8.06 (3H, m); 7.94～7.91 (1H, m); 7.86～7.73 (5H, m); 7.70～7.66 (1H, m); 7.62～7.49 (6H, m); 7.47～7.43 (1H, m) ;7.38～7.34(1H,m).
参照上述类似的合成方法，制备以下化合物：
Referring to the above-mentioned similar synthetic methods, prepare the following compounds:
Referring to the above-mentioned similar synthetic methods, prepare the following compounds:
实施例3Example 3
化合物N521的制备：
Preparation of compound N521:
Preparation of compound N521:
15.0mmol化合物C1溶解于80mL干燥的甲苯中，在氮气保护下，加入16.5mmol的2-([1，1′-联苯基]-4-基)-4-(2-溴苯基)-6-苯基-1，3，5-三嗪和22.5mmol的叔丁醇钠，再加入0.1mmol的Pd2(dba)3CHCl3和0.02mL的10％三叔丁基磷甲苯溶液，升温至100℃，搅拌反应15小时，冷却到室温，加入50mL水稀释，用二氯甲烷萃取，收集有机相，干燥，过滤，滤液减压浓缩干，用硅胶柱分离纯化，得到化合物N521，黄色固体，收率：84％，MS(MALDI-TOF)：m/z 714.2663[M+H]+；1HNMR(δ、CDCl3)：8.74～8.71(1H，m)；8.49～8.45(5H，m)；8.38～8.32(3H，m)；8.13～8.04(2H，m)；7.92～7.87(4H，m)；7.79～7.75(1H，m)；7.60～7.37(14H，m)；7.34～7.29(1H，m)。15.0 mmol of compound C1 was dissolved in 80 mL of dry toluene, and 16.5 mmol of 2-([1,1′-biphenyl]-4-yl)-4-(2-bromophenyl)- was added under nitrogen protection. 6-phenyl-1,3,5-triazine and 22.5mmol sodium tert-butoxide, then add 0.1mmol Pd 2 (dba) 3 CHCl 3 and 0.02mL of 10% tri-tert-butylphosphorus toluene solution, and raise the temperature to 100°C, stir the reaction for 15 hours, cool to room temperature, add 50 mL of water to dilute, extract with dichloromethane, collect the organic phase, dry, filter, and concentrate the filtrate to dryness under reduced pressure, and separate and purify with a silica gel column to obtain compound N521, a yellow solid , Yield: 84%, MS (MALDI-TOF): m/z 714.2663[M+H] + ; 1 HNMR (δ, CDCl 3 ): 8.74～8.71 (1H, m); 8.49～8.45 (5H, m ); 8.38～8.32 (3H, m); 8.13～8.04 (2H, m); 7.92～7.87 (4H, m); 7.79～7.75 (1H, m); 7.60～7.37 (14H, m); 7.34～7.29 (1H,m).
参照上述类似的合成方法，制备以下化合物：
Referring to the above-mentioned similar synthetic methods, prepare the following compounds:
Referring to the above-mentioned similar synthetic methods, prepare the following compounds:
有机电致发光元件的制备Preparation of organic electroluminescent components
对比例1Comparative example 1
将下述的化合物C作为空穴注入材料，化合物D作为空穴传输材料、化合物E作为红光主体材料，化合物F作为红光掺杂材料，化合物G作为电子传输掺杂材料，LiQ作为电子传输主体材料。
The following compound C is used as a hole injection material, compound D is used as a hole transport material, compound E is used as a red light host material, compound F is used as a red light doping material, compound G is used as an electron transport doping material, and LiQ is used as an electron transport material Subject material.
The following compound C is used as a hole injection material, compound D is used as a hole transport material, compound E is used as a red light host material, compound F is used as a red light doping material, compound G is used as an electron transport doping material, and LiQ is used as an electron transport material Subject material.
将化合物
依次采用DOV公司制造的EL蒸镀机蒸镀到ITO玻璃上制作OLED对比元件1。compound The EL evaporation machine manufactured by DOV Company was used to evaporate onto the ITO glass in order to produce the OLED contrast element 1.
试验例1Test example 1
按照对比例1的方法制备OLED元件，其中，将前述的化合物E替换为本发明的化合物N313～N582中的任一种或多种，制备有机电致发光元件，Prepare an OLED element according to the method of Comparative Example 1, wherein the aforementioned compound E is replaced with any one or more of the compounds N313 to N582 of the present invention to prepare an organic electroluminescent element,
元件结构：
Component structure:
对上述过程制备的有机电致发光元件进行如下性能测试：The organic electroluminescent elements prepared by the above process were subjected to the following performance tests:
在同样亮度下，使用数字源表及亮度计测定试验例1及对比例1中制备得到的有机电致发光元件的驱动电压和电流效率以及元件的寿命。具体而言，以每秒0.1V的速率提升电压，测定当有机电致发光元件的亮度达到1000cd/m2时的电压即驱动电压，同时测出此时的电流密度；亮度与电流密度的比值即为电流效率；LT90％寿命测试如下：使用亮度计在1000cd/m2亮度下，保持恒定的电流，测量有机电致发光元件的亮度衰减为900cd/m2的时间，单位为小时。
Under the same brightness, a digital source meter and a luminance meter were used to measure the driving voltage and current efficiency of the organic electroluminescent elements prepared in Test Example 1 and Comparative Example 1, as well as the lifetime of the elements. Specifically, increase the voltage at a rate of 0.1V per second, measure the voltage when the brightness of the organic electroluminescent element reaches 1000cd/ m2 , which is the driving voltage, and measure the current density at this time; the ratio of brightness to current density That is the current efficiency; the LT90% life test is as follows: use a luminance meter to maintain a constant current at a brightness of 1000cd/ m2 , and measure the time for the brightness of the organic electroluminescent element to decay to 900cd/ m2 , in hours.
表1各元件性能检测结果
Table 1 Performance test results of each component
Table 1 Performance test results of each component
表5中，NPh、NNap、NPhPh表示的结构如下：
In Table 5, the structures represented by NPh, NNap, and NPhPh are as follows:
In Table 5, the structures represented by NPh, NNap, and NPhPh are as follows:
由表1可知，本发明的化合物用于有机电致发光元件的主体材料时，电流效率可达到23.0cd/A以上，同时寿命大幅度提高，是性能良好的主体材料。As can be seen from Table 1, when the compound of the present invention is used as the host material of an organic electroluminescent element, the current efficiency can reach more than 23.0cd/A, and the life span is greatly improved, making it a host material with good performance.
对比例1中的化合物E与本发明的化合物相比，区别在于两个接合的咔唑为扭曲构型，空间位阻偏大，平面共轭能力弱。而本发明的化合物为苯并咔唑接合的吲哚为平面的大共轭结构，位阻较小，对分子成膜的影响较小，所以其在分子成膜及电荷的传输性能上均较优异，元件内电荷的传输更加平衡，元件性能提高。Comparing Compound E in Comparative Example 1 with the compound of the present invention, the difference lies in that the two joined carbazoles have a twisted configuration, greater steric hindrance, and weak planar conjugation ability. The compound of the present invention is a large planar conjugated structure in which benzocarbazole-joined indole has less steric hindrance and less impact on molecular film formation. Therefore, it has better molecular film formation and charge transport properties. Excellent, the charge transfer within the component is more balanced and the component performance is improved.
表1中仅列举了N313～N582中部分化合物的性能，其他化合物性能与表中列举的化合物的数据基本一致，由于篇幅有限，不再一一列举。Table 1 only lists the properties of some compounds among N313~N582. The properties of other compounds are basically consistent with the data of the compounds listed in the table. Due to limited space, they will not be listed one by one.
以上所述，仅为本发明的具体实施方式，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，可轻易想到变化或替换，都应涵盖在本发明的保护范围之内。因此，本发明的保护范围应以所述权利要求的保护范围为准。
The above are only specific embodiments of the present invention, but the protection scope of the present invention is not limited thereto. Any person familiar with the technical field can easily think of changes or substitutions within the technical scope disclosed by the present invention. should be covered by the protection scope of the present invention. Therefore, the protection scope of the present invention should be subject to the protection scope of the claims.
Claims (10)
- 一种吲哚衍生物，其特征在于，所述吲哚衍生物的结构如式(I)所示：
An indole derivative, characterized in that the structure of the indole derivative is as shown in formula (I):
其中，W1和W2代表式(II)所示的基团；
Among them, W 1 and W 2 represent groups represented by formula (II);
Z各自独立地表示CR0或N；Z independently represents CR 0 or N;相邻的两个“^”指示式(I)中相邻的基团W1和W2；Two adjacent "^" indicate adjacent groups W 1 and W 2 in formula (I);R0、R1、R2、R3、R4、R5、R6、R7、R8、R9各自独立地选自由氢、氘、卤素、腈基、C1-C40的烷基、C3-C40的环烷基或带有支链的烷基、取代或未取代的C6-C60芳基、取代或未取代的C6-C60稠环芳基、取代或未取代的C6-C60芳胺基、取代或未取代的C2-C60杂芳基组成的群组，并且任意相邻的两个或多个基团可任选地接合或稠合形成另外的一个或多个取代或未取代的环，在所形成的环中含有或不含有一个或多个杂原子N、P、B、O或S；R 0 , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 are each independently selected from hydrogen, deuterium, halogen, nitrile, and C 1 -C 40 alkane. group, C 3 -C 40 cycloalkyl or branched alkyl group, substituted or unsubstituted C 6 -C 60 aryl group, substituted or unsubstituted C 6 -C 60 fused ring aryl group, substituted or The group consisting of unsubstituted C 6 -C 60 arylamine groups, substituted or unsubstituted C 2 -C 60 heteroaryl groups, and any two or more adjacent groups may be optionally joined or fused Forming one or more additional substituted or unsubstituted rings with or without one or more heteroatoms N, P, B, O or S in the formed ring;Ar1选自由取代或未取代的C6-C60芳基、取代或未取代的C2-C60杂芳基组成的群组；Ar 1 is selected from the group consisting of substituted or unsubstituted C 6 -C 60 aryl group and substituted or unsubstituted C 2 -C 60 heteroaryl group;L选自由取代或未取代的C6-C60亚芳基、取代或未取代的C2-C60亚杂芳基组成的群组。L is selected from the group consisting of substituted or unsubstituted C 6 -C 60 arylene, substituted or unsubstituted C 2 -C 60 heteroarylene. - 根据权利要求1所述的吲哚衍生物，其特征在于，所述吲哚衍生物选自由式I-1或式I-2组成的群组：
The indole derivative according to claim 1, characterized in that the indole derivative is selected from the group consisting of formula I-1 or formula I-2:
Z各自独立地为CR0；Z is independently CR 0 ;Ar1选自取代或未取代的C2-C60杂芳基；Ar 1 is selected from substituted or unsubstituted C 2 -C 60 heteroaryl;L选自由取代或未取代的C6-C60亚芳基、取代或未取代的C2-C60亚杂芳基组成的群组；L is selected from the group consisting of substituted or unsubstituted C 6 -C 60 arylene, substituted or unsubstituted C 2 -C 60 heteroarylene;R0、R1、R2、R3、R4、R5、R6、R7、R8、R9各自独立地选自由以下基团组成的群组：氢、氘、取代或未取代的C6-C60芳基或取代或未取代的C2-C60杂芳基。R 0 , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 are each independently selected from the group consisting of: hydrogen, deuterium, substituted or unsubstituted C 6 -C 60 aryl or substituted or unsubstituted C 2 -C 60 heteroaryl. - 根据权利要求1或2所述的吲哚衍生物，其特征在于，所述杂芳基选自由以下II-1～II-17所示基团组成的群组：
The indole derivative according to claim 1 or 2, characterized in that the heteroaryl group is selected from the group consisting of the following groups II-1 to II-17:
其中，in,Z1、Z2各自独立地选自由氢、氘、卤素、羟基、腈基、硝基、氨基、脒基、肼基、腙基、羧基或其羧酸盐、磺酸基或其磺酸盐、磷酸基或其磷酸盐、C1-C40烷基、C2-C40烯基、C2-C40炔基、C1-C40烷氧基、C3-C40环烷烃基、C3-C40环烯烃基、取代或未取代的C6-C60芳基、取代或未取代的C6-C60芳氧基、取代或未取代的C6-C60芳硫醚基、或者取代或未取代的C2-C60杂环芳基组成的群组；Z 1 and Z 2 are each independently selected from hydrogen, deuterium, halogen, hydroxyl, nitrile group, nitro group, amino group, amidine group, hydrazine group, hydrazone group, carboxyl group or its carboxylate, sulfonic acid group or its sulfonate , phosphate group or its phosphate, C 1 -C 40 alkyl group, C 2 -C 40 alkenyl group, C 2 -C 40 alkynyl group, C 1 -C 40 alkoxy group, C 3 -C 40 cycloalkyl group, C 3 -C 40 cycloalkenyl group, substituted or unsubstituted C 6 -C 60 aryl group, substituted or unsubstituted C 6 -C 60 aryloxy group, substituted or unsubstituted C 6 -C 60 aryl sulfide group , or a group consisting of substituted or unsubstituted C 2 -C 60 heterocyclic aryl groups;x1表示1-4的整数；x2表示1-3的整数；x3表示1或2；x4表示1-6的整数；x5表示1-5的整数；x1 represents an integer from 1 to 4; x2 represents an integer from 1 to 3; x3 represents 1 or 2; x4 represents an integer from 1 to 6; x5 represents an integer from 1 to 5;T1表示O、S、CR’R”或NAr’；T 1 means O, S, CR'R" or NAr';R’、R”各自独立地选自由氢、氘、C1～C40的烷基、C1～C40的杂烷基、取代或未取代的C6-C60芳基、取代或未取代的C6-C60芳胺基、或者取代或未取代的C2-C60杂环芳基组成的群组，R’和R”可任选地接合或稠合形成另外的一个多个取代或未取代的环，在所形成的环中含有或不含有一个或多个杂原子N、P、B、O或S；优选地，R’、R”为甲基、苯基或芴基；R', R" are each independently selected from hydrogen, deuterium, C 1 to C 40 alkyl group, C 1 to C 40 heteroalkyl group, substituted or unsubstituted C 6 to C 60 aryl group, substituted or unsubstituted A group consisting of C 6 -C 60 arylamine groups, or substituted or unsubstituted C 2 -C 60 heterocyclic aryl groups, R' and R" can optionally be joined or fused to form another multiple substituted Or an unsubstituted ring, containing or not containing one or more heteroatoms N, P, B, O or S in the formed ring; preferably, R', R" is methyl, phenyl or fluorenyl;Ar’选自由C1～C40的烷基、C1～C40的杂烷基、C3～C40的环烷基、取代或未取代的C6-C60芳基、取代或未取代的C6-C60稠环芳基、取代或未取代的C6-C60芳胺基、或者取代或未取代的C2-C60杂环芳基组成的群组；优选地，Ar’为甲基、乙基、苯基、联苯基或萘基；Ar' is selected from C 1 to C 40 alkyl, C 1 to C 40 heteroalkyl, C 3 to C 40 cycloalkyl, substituted or unsubstituted C 6 -C 60 aryl, substituted or unsubstituted A group consisting of a C 6 -C 60 fused ring aryl group, a substituted or unsubstituted C 6 -C 60 arylamine group, or a substituted or unsubstituted C 2 -C 60 heterocyclic aryl group; preferably, Ar' is methyl, ethyl, phenyl, biphenyl or naphthyl;表示取代基与杂芳基的连接键。 Indicates the bond between the substituent and the heteroaryl group. - 根据权利要求1～3任一项所述的吲哚衍生物，其特征在于，所述Ar1选自由以下III-1～III-18所示基团组成的群组：
The indole derivative according to any one of claims 1 to 3, wherein Ar 1 is selected from the group consisting of the following groups III-1 to III-18:
其中，T2选自O或S；Among them, T 2 is selected from O or S;R10、R11各自独立地选自由氢、氘、取代或未取代的C6～C60芳基、取代或未取代的C2～C60杂芳基组成的群组；R 10 and R 11 are each independently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted C 6 to C 60 aryl groups, and substituted or unsubstituted C 2 to C 60 heteroaryl groups;R12选自由氢、氘、C1～C40的烷基、取代或未取代的C6-C60芳基、或者取代或未取代的C2-C60杂芳基组成的群组；R12为一个或多个至饱和取代；R 12 is selected from the group consisting of hydrogen, deuterium, C 1 to C 40 alkyl, substituted or unsubstituted C 6 -C 60 aryl, or substituted or unsubstituted C 2 -C 60 heteroaryl; R 12 is one or more saturated substitutions;*-表示Ar1取代基与L的连接键。*-Indicates the bond between Ar 1 substituent and L. - 根据权利要求1-4任意一项所述的吲哚衍生物，其特征在于，所述R10、R11各自独立地选自由苯基、联苯基、三联苯基、萘基、菲基、三亚苯基、萘取代的苯基、菲取代的苯基、二苯并呋喃基、二苯并噻吩基、咔唑基、二苯并呋喃取代的苯基、二苯并噻吩取代的苯基、苯基取代的咔唑基、萘基取代的咔唑基、联苯取代的咔唑基、9-苯基咔唑基、苯并萘并呋喃基、苯并萘并噻吩基或苯基取代的苯并咔唑基组成的群组；The indole derivative according to any one of claims 1 to 4, wherein R 10 and R 11 are each independently selected from phenyl, biphenyl, terphenyl, naphthyl, phenanthrenyl, triphenylene, naphthalene-substituted phenyl, phenanthrene-substituted phenyl, dibenzofuranyl, dibenzothienyl, carbazolyl, dibenzofuran-substituted phenyl, dibenzothiophene-substituted phenyl, Phenyl-substituted carbazolyl, naphthyl-substituted carbazolyl, biphenyl-substituted carbazolyl, 9-phenylcarbazolyl, benzonaphthofuranyl, benzonaphthienyl or phenyl-substituted A group composed of benzocarbazolyl groups;R12为氢或氘。R 12 is hydrogen or deuterium.
- 根据权利要求1所述的吲哚衍生物，其特征在于，所述L选自单键、亚苯基、亚吡啶基或萘二基；The indole derivative according to claim 1, characterized in that, the L is selected from a single bond, phenylene, pyridylene or naphthalenediyl;R0、R1、R2、R3、R4、R5、R6、R7、R8和R9都为氢。R 0 , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are all hydrogen.
- 根据权利要求1～6任一项所述的吲哚衍生物，其特征在于，所述的吲哚衍生物为以下N313～N582所示结构中的一种：
The indole derivative according to any one of claims 1 to 6, characterized in that the indole derivative is one of the following structures N313 to N582:
其中，*-T3-*选自*-O-*、*-S-*或下述结构中的一种：
Among them, *-T 3 -* is selected from *-O-*, *-S-* or one of the following structures:
*-和-*表示连接键。*- and -* represent connection keys. - 一种有机电致发光元件，其特征在于，包括第一电极、第二电极、封盖层和置于第一电极和第二电极之间的至少一层有机层，所述的有机层或封盖层中至少一层包括权利要求1-7任意一项所述的吲哚衍生物。An organic electroluminescent element, characterized by comprising a first electrode, a second electrode, a capping layer and at least one organic layer placed between the first electrode and the second electrode, the organic layer or capping layer At least one layer of the cover layer includes the indole derivative according to any one of claims 1-7.
- 一种显示装置，其特征在于，包括权利要求8所述的有机电致发光元件。A display device, characterized by comprising the organic electroluminescent element according to claim 8.
- 一种照明装置，其特征在于，包括权利要求8所述的有机电致发光元件。 A lighting device, characterized by comprising the organic electroluminescent element according to claim 8.
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Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20170092128A (en) * | 2016-02-02 | 2017-08-10 | 주식회사 엘지화학 | Hetero-cyclic compound and organic light emitting device comprising the same |
| WO2020122461A1 (en) * | 2018-12-14 | 2020-06-18 | 덕산네오룩스 주식회사 | Compound for organic electric device, organic electric device using same, and electronic apparatus thereof |
| WO2020130378A1 (en) * | 2018-12-19 | 2020-06-25 | 덕산네오룩스 주식회사 | Compound for organic electric element, organic electric element using same, and electronic device comprising same |
| CN112375082A (en) * | 2020-11-23 | 2021-02-19 | 北京八亿时空液晶科技股份有限公司 | Series of carbazole derivatives and application thereof |
| CN112442041A (en) * | 2020-11-23 | 2021-03-05 | 北京八亿时空液晶科技股份有限公司 | Carbazole derivative and application thereof |
| CN112480128A (en) * | 2020-11-23 | 2021-03-12 | 北京八亿时空液晶科技股份有限公司 | Carbazole derivative and application thereof |
| CN112707904A (en) * | 2020-12-28 | 2021-04-27 | 北京八亿时空液晶科技股份有限公司 | Naphthalene bisindole derivative and application thereof |
| CN114891000A (en) * | 2022-04-26 | 2022-08-12 | 北京八亿时空液晶科技股份有限公司 | Indole derivative, organic electroluminescent element, display device and lighting device |
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Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20170092128A (en) * | 2016-02-02 | 2017-08-10 | 주식회사 엘지화학 | Hetero-cyclic compound and organic light emitting device comprising the same |
| WO2020122461A1 (en) * | 2018-12-14 | 2020-06-18 | 덕산네오룩스 주식회사 | Compound for organic electric device, organic electric device using same, and electronic apparatus thereof |
| WO2020130378A1 (en) * | 2018-12-19 | 2020-06-25 | 덕산네오룩스 주식회사 | Compound for organic electric element, organic electric element using same, and electronic device comprising same |
| CN112375082A (en) * | 2020-11-23 | 2021-02-19 | 北京八亿时空液晶科技股份有限公司 | Series of carbazole derivatives and application thereof |
| CN112442041A (en) * | 2020-11-23 | 2021-03-05 | 北京八亿时空液晶科技股份有限公司 | Carbazole derivative and application thereof |
| CN112480128A (en) * | 2020-11-23 | 2021-03-12 | 北京八亿时空液晶科技股份有限公司 | Carbazole derivative and application thereof |
| CN112707904A (en) * | 2020-12-28 | 2021-04-27 | 北京八亿时空液晶科技股份有限公司 | Naphthalene bisindole derivative and application thereof |
| CN114891000A (en) * | 2022-04-26 | 2022-08-12 | 北京八亿时空液晶科技股份有限公司 | Indole derivative, organic electroluminescent element, display device and lighting device |
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