CN114276366A - Indole derivative and application thereof - Google Patents
Indole derivative and application thereof Download PDFInfo
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- CN114276366A CN114276366A CN202110424920.6A CN202110424920A CN114276366A CN 114276366 A CN114276366 A CN 114276366A CN 202110424920 A CN202110424920 A CN 202110424920A CN 114276366 A CN114276366 A CN 114276366A
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- China
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- group
- groups
- aromatic
- heteroaromatic ring
- substituted
- Prior art date
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- 150000002475 indoles Chemical class 0.000 title claims abstract description 33
- 239000000463 material Substances 0.000 claims abstract description 46
- 239000010410 layer Substances 0.000 claims description 59
- 125000003118 aryl group Chemical group 0.000 claims description 41
- 125000004432 carbon atom Chemical group C* 0.000 claims description 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 125000002560 nitrile group Chemical group 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 125000004122 cyclic group Chemical group 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 11
- 229910052805 deuterium Inorganic materials 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 238000006467 substitution reaction Methods 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 8
- 125000002950 monocyclic group Chemical group 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 230000000903 blocking effect Effects 0.000 claims description 7
- 125000004431 deuterium atom Chemical group 0.000 claims description 7
- 150000001975 deuterium Chemical group 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 239000012044 organic layer Substances 0.000 claims description 5
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Chemical group 0.000 claims description 3
- 239000010409 thin film Substances 0.000 claims description 3
- 230000005669 field effect Effects 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000004437 phosphorous atom Chemical group 0.000 claims description 2
- 125000003367 polycyclic group Chemical group 0.000 claims description 2
- 229940037201 oris Drugs 0.000 claims 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 abstract description 4
- 229940054051 antipsychotic indole derivative Drugs 0.000 abstract description 4
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 abstract description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 description 45
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 150000003254 radicals Chemical class 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- -1 aliphatic hydrocarbon radicals Chemical class 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000000706 filtrate Substances 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 239000000741 silica gel Substances 0.000 description 11
- 229910002027 silica gel Inorganic materials 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- 238000001035 drying Methods 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 7
- 125000001072 heteroaryl group Chemical group 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 238000010790 dilution Methods 0.000 description 5
- 239000012895 dilution Substances 0.000 description 5
- 239000002019 doping agent Substances 0.000 description 5
- 230000005525 hole transport Effects 0.000 description 5
- 101100317378 Mus musculus Wnt3 gene Proteins 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 125000005605 benzo group Chemical group 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 4
- 238000007639 printing Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 102000008016 Eukaryotic Initiation Factor-3 Human genes 0.000 description 3
- 108010089790 Eukaryotic Initiation Factor-3 Proteins 0.000 description 3
- 101100446506 Mus musculus Fgf3 gene Proteins 0.000 description 3
- 101100348848 Mus musculus Notch4 gene Proteins 0.000 description 3
- 101000767160 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) Intracellular protein transport protein USO1 Proteins 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000005401 electroluminescence Methods 0.000 description 3
- 238000005538 encapsulation Methods 0.000 description 3
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- 238000011056 performance test Methods 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- HNZUKQQNZRMNGS-UHFFFAOYSA-N 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine Chemical compound BrC1=CC=CC(C=2N=C(N=C(N=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 HNZUKQQNZRMNGS-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 230000008021 deposition Effects 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
- 238000000605 extraction Methods 0.000 description 2
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 description 2
- 229950000688 phenothiazine Drugs 0.000 description 2
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 2
- 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 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- BKWVXPCYDRURMK-UHFFFAOYSA-N (2,6-dimethoxyphenyl)boronic acid Chemical compound COC1=CC=CC(OC)=C1B(O)O BKWVXPCYDRURMK-UHFFFAOYSA-N 0.000 description 1
- ICPSWZFVWAPUKF-UHFFFAOYSA-N 1,1'-spirobi[fluorene] Chemical compound C1=CC=C2C=C3C4(C=5C(C6=CC=CC=C6C=5)=CC=C4)C=CC=C3C2=C1 ICPSWZFVWAPUKF-UHFFFAOYSA-N 0.000 description 1
- FIARMZDBEGVMLV-UHFFFAOYSA-N 1,1,2,2,2-pentafluoroethanolate Chemical group [O-]C(F)(F)C(F)(F)F FIARMZDBEGVMLV-UHFFFAOYSA-N 0.000 description 1
- HQDYNFWTFJFEPR-UHFFFAOYSA-N 1,2,3,3a-tetrahydropyrene Chemical compound C1=C2CCCC(C=C3)C2=C2C3=CC=CC2=C1 HQDYNFWTFJFEPR-UHFFFAOYSA-N 0.000 description 1
- ZFXBERJDEUDDMX-UHFFFAOYSA-N 1,2,3,5-tetrazine Chemical compound C1=NC=NN=N1 ZFXBERJDEUDDMX-UHFFFAOYSA-N 0.000 description 1
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical compound C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 1
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical compound C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- HTJMXYRLEDBSLT-UHFFFAOYSA-N 1,2,4,5-tetrazine Chemical compound C1=NN=CN=N1 HTJMXYRLEDBSLT-UHFFFAOYSA-N 0.000 description 1
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 description 1
- YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical compound C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 description 1
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 description 1
- UDGKZGLPXCRRAM-UHFFFAOYSA-N 1,2,5-thiadiazole Chemical compound C=1C=NSN=1 UDGKZGLPXCRRAM-UHFFFAOYSA-N 0.000 description 1
- DXBHBZVCASKNBY-UHFFFAOYSA-N 1,2-Benz(a)anthracene Chemical compound C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=C1 DXBHBZVCASKNBY-UHFFFAOYSA-N 0.000 description 1
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 description 1
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 description 1
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
- ZKAMEFMDQNTDFK-UHFFFAOYSA-N 1h-imidazo[4,5-b]pyrazine Chemical compound C1=CN=C2NC=NC2=N1 ZKAMEFMDQNTDFK-UHFFFAOYSA-N 0.000 description 1
- GZPPANJXLZUWHT-UHFFFAOYSA-N 1h-naphtho[2,1-e]benzimidazole Chemical compound C1=CC2=CC=CC=C2C2=C1C(N=CN1)=C1C=C2 GZPPANJXLZUWHT-UHFFFAOYSA-N 0.000 description 1
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
- TWZSIAFEFBKCNN-UHFFFAOYSA-N 2,3-dibromo-1-benzothiophene Chemical compound C1=CC=C2C(Br)=C(Br)SC2=C1 TWZSIAFEFBKCNN-UHFFFAOYSA-N 0.000 description 1
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 1
- UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical compound C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 description 1
- LYTMVABTDYMBQK-UHFFFAOYSA-N 2-benzothiophene Chemical compound C1=CC=CC2=CSC=C21 LYTMVABTDYMBQK-UHFFFAOYSA-N 0.000 description 1
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- HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical compound C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 description 1
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- QQTOBDXDQYCGMA-UHFFFAOYSA-N naphtho[2,3-e][1,3]benzoxazole Chemical compound C1=CC=C2C=C3C(N=CO4)=C4C=CC3=CC2=C1 QQTOBDXDQYCGMA-UHFFFAOYSA-N 0.000 description 1
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Abstract
The present invention relates to a series of indole derivatives, applications thereof, and organic electroluminescent elements, display devices, and lighting devices containing the indole derivatives. The structural formula of the indole derivative is shown as a formula (I), the indole derivative has high stability and triplet energy level, is suitable for being used as a material for an organic electroluminescent element, and contains the indole derivativeThe material for organic electroluminescent element has the characteristics of low starting voltage, high luminous efficiency and high brightness.
Description
Technical Field
The invention belongs to the technical field of materials for organic electroluminescent elements, and particularly relates to an indole derivative and application thereof.
Background
In recent years, organic electroluminescent display technologies have become mature, and some products have already entered the market, but in the course of industrialization, many problems still need to be solved, especially for various organic materials used for manufacturing devices, there are many problems that are still unsolved, such as carrier injection and transport properties, electroluminescent properties of materials, service life, color purity, matching between various materials and between various electrodes, and the like. Especially, the light emitting element has not yet achieved practical requirements in terms of luminous efficiency and service life, which greatly limits the development of OLED technology.
Organic electroluminescence is largely divided into fluorescence and phosphorescence, but according to the spin quantum statistical theory, the probability of singlet excitons and triplet excitons is 1:3, i.e., the theoretical limit of fluorescence from radiative transitions of singlet excitons is 25%, and the theoretical limit of fluorescence from radiative transitions of triplet excitons is 75%. It is urgent to use 75% of the energy of triplet excitons. Forrest et al discovered in 1997 that the phosphorescence electroluminescence phenomenon breaks through the limit of 25% efficiency of the quantum efficiency of the organic electroluminescence material, and arouses people to pay extensive attention to the metal complex phosphorescence material. Since then, much research has been conducted on phosphorescent materials.
The present invention has been made in view of the above circumstances.
Disclosure of Invention
In order to solve the above problems of the prior art, the present invention provides a novel indole derivative which is a raw material for an organic electroluminescent element material and can provide an organic electroluminescent element material and an organic electroluminescent element having a reduced starting voltage, a high luminous efficiency, and an improved luminance.
In order to achieve the purpose, the invention adopts the following technical scheme:
an indole derivative having a structural formula as shown in formula (I):
wherein any two adjacent groups W1、W2、W3、W4Represents a group of the following formula (II),
wherein Z, identically or differently at each occurrence, denotes CR5Or N, and ^ indicates the corresponding adjacent group W in formula I1And W2、W2And W3Or W3And W4；
T1Representation O, S, NAr2Or CR6R7；
R1～R7Same or different, selected from hydrogen, deuterium, having C1～C40Straight chain alkyl of (2) having C1～C40Linear heteroalkyl group of (A) having C3～C40A branched or cyclic alkyl group having C3～C40A branched or cyclic heteroalkyl group of (A) having C2～C40Alkenyl or alkynyl group of (A), an aromatic ring system or a heteroaromatic ring system having 5 to 60 carbon atoms, R1～R7Each of which may be substituted by one or more groups R, and wherein two or more adjacent substituent groups may optionally be joined or fused to form a mono-or polycyclic aliphatic, aromatic or heteroaromatic ring system;
Ar1、Ar2same or different, selected from the group consisting of having C1～C40Straight chain alkyl of (2) having C1～C40Linear heteroalkyl group of (A) having C3～C40A branched or cyclic alkyl group having C3～C40A branched or cyclic heteroalkyl group of (A) having C2～C40Alkenyl or alkynyl groups of (a), aromatic or heteroaromatic ring systems having 5 to 60 carbon atoms, which ring systems may be substituted by one or more radicals R;
each occurrence of R is the same or different and is selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a nitrile group, a nitro group, and N (Ar)3)2、N(R12)2、C(＝O)Ar3、C(＝O)R8、P(＝O)(Ar3)2Having a structure of C1～C40Straight chain alkyl of (2) having C1～C40Linear heteroalkyl group of (A) having C3～C40A branched or cyclic alkyl group having C3～C40A branched or cyclic heteroalkyl group of (A) having C2～C40Alkenyl or alkynyl groups of (A), aromatic or heteroaromatic ring systems having from 5 to 80 carbon atoms, aryloxy or heteroaryloxy groups having from 5 to 60 carbon atoms, each of the R groups being optionally substituted by one or more radicals R8Substituted, or combinations of these systems, wherein one or more non-adjacent-CH2The radicals may be substituted by R8C＝CR8、C≡C、Si(R8)2、Ge(R8)2、Sn(R8)2、C＝O、C＝S、C＝Se、C＝NR8、P(＝O)(R8)、SO、SO2、NR8O, S or CONR8And in which one or more hydrogen atoms are replaced by deuterium atoms, halogen atoms, nitrile groups or nitro groups, where two or more adjacent substituents R may optionally be joined or fused to form a mono-or polycyclic, aliphatic, aromatic or heteroaromatic ring system which may be interrupted by one or more radicals R8Substitution;
R8each occurrence of the same or different is selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a nitrile group, a nitro group, and N (Ar)3)2、N(R9)2、C(＝O)Ar3、C(＝O)R9、P(＝O)(Ar3)2Having a structure of C1～C40Straight chain alkyl of (2) having C1～C40Linear heteroalkyl group of (A) having C3～C40A branched or cyclic alkyl group having C3～C40A branched or cyclic heteroalkyl group of (A) having C2～C40One of alkenyl or alkynyl, aromatic or heteroaromatic ring system having 5 to 60 carbon atoms, aryloxy or heteroaryloxy having 5 to 60 carbon atoms, R8Each radical in (a) may be substituted by one or more radicals R9Substituted, or combinations of these systems, wherein one or more non-adjacent-CH2The radicals may be substituted by R9C＝CR9、C≡C、Si(R9)2、Ge(R9)2、Sn(R9)2、C＝O、C＝S、C＝Se、C＝NR9、P(＝O)(R9)、SO、SO2、NR9O, S or CONR9And wherein one or more hydrogen atoms may be replaced by deuterium atoms, halogen atoms, nitrile groups or nitro groups, wherein two or more adjacent substituents R8Aliphatic, aromatic or heteroaromatic ring systems which may optionally be joined or fused to form a single ring or multiple rings and which may be interrupted by one or more radicals R9Substitution;
Ar3identical or different at each occurrence and selected from aromatic or heteroaromatic ring systems having from 5 to 30 carbon atoms which may be substituted by one or more nonaromatic radicals R9Substitution; two groups Ar here bonded to the same nitrogen or phosphorus atom3Can also be selected from N (R) through a single bond9)、C(R9)2Oxygen or sulfur bridging groups;
R9selected from hydrogen atom, deuterium atom, fluorine atom, nitrile group, having C1～C20An aliphatic hydrocarbon group, an aromatic ring or a heteroaromatic ring system having 5 to 30 carbon atoms, wherein R9Wherein one or more hydrogen atoms may be replaced by deuterium atoms, halogen atoms, or nitrile groups, two or more of which are taken adjacentlySubstituent R9They can form mono-or polycyclic aliphatic, aromatic or heteroaromatic ring systems with one another.
Aromatic or heteroaromatic ring systems in the sense of the present invention are intended to be taken to mean systems which do not necessarily contain only aryl or heteroaryl groups, but in which a plurality of aryl or heteroaryl groups may also be linked by non-aromatic units, for example C, N, O or an S atom. Thus, for example, as with systems in which two or more aryl groups are linked by, for example, a short alkyl group, systems such as fluorene, 9' -spirobifluorene, 9-diarylfluorene, triarylamine, diaryl ether, and the like are also considered to refer to aromatic ring systems in the sense of the present invention.
Aryl in the sense of the present invention contains 5 to 60 carbon atoms and heteroaryl in the sense of the present invention contains 5 to 60 carbon atoms and at least one heteroatom, with the proviso that the sum of carbon atoms and heteroatoms is at least 5; the heteroatom is preferably selected from N, O or S. Aryl or heteroaryl herein is considered to mean a simple aromatic ring, i.e. benzene, naphthalene, etc., or a simple heteroaromatic ring, such as pyridine, pyrimidine, thiophene, etc., or a fused aryl or heteroaryl group, such as anthracene, phenanthrene, quinoline, isoquinoline, etc. Aromatic rings, such as biphenyl, which are connected to one another by single bonds, are, in contrast, not referred to as aryl or heteroaryl groups, but rather as aromatic ring systems.
Containing 1 to 40 carbon atoms and in which the individual hydrogen atoms or-CH2The aliphatic hydrocarbon radicals or alkyl or alkenyl or alkynyl radicals which may also be substituted by the abovementioned radicals are preferably to be understood as meaning the following radicals: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, neopentyl, cyclopentyl, n-hexyl, neohexyl, cyclohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl or octynyl. The alkoxy group, preferably an alkoxy group having 1 to 40 carbon atoms, is considered to mean a methoxy group, a trifluoromethoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, an isobutoxy group, a sec-butoxy group, a tert-butoxy group, an n-pentyloxy groupAlkyl, sec-pentyloxy, 2-methylbutyloxy, n-hexyloxy, cyclohexyloxy, n-heptyloxy, cycloheptyloxy, n-octyloxy, cyclooctyloxy, 2-ethylhexyloxy, pentafluoroethoxy and 2,2, 2-trifluoroethoxy. The heteroalkyl group is preferably an alkyl group having 1 to 40 carbon atoms, meaning a hydrogen atom or-CH alone2The radicals-which may be substituted by oxygen, sulfur or halogen atoms-are understood to mean alkoxy, alkylthio, fluorinated alkoxy, fluorinated alkylthio, in particular methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio, tert-butylthio, trifluoromethylthio, trifluoromethoxy, pentafluoroethoxy, pentafluoroethylthio, 2,2, 2-trifluoroethoxy, 2,2, 2-trifluoroethylthio, vinyloxy, propenyloxy, propenylthio, butenylthio, butenyloxy, pentenylthio, cyclopentenyloxy, cyclopentenylthio, hexenyloxy, hexenylthio, cyclohexenyloxy, cyclohexenylthio, ethynyloxy, propenylthio, butenyloxy, cyclohexenylthio, ethynyloxy, Ethynylthio, propynyloxy, propynylthio, butynyloxy, butynylthio, pentynyloxy, pentynylthio, hexynyloxy, hexynylthio.
In general, the cycloalkyl, cycloalkenyl groups according to the invention may be cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptyl, cycloheptenyl, where one or more-CH may be present2The radicals may be replaced by the radicals mentioned above; furthermore, one or more hydrogen atoms may also be replaced by deuterium atoms, halogen atoms, or nitrile groups.
The aromatic or heteroaromatic ring atoms according to the invention may in each case also be substituted by the abovementioned radicals R9Substituted aromatic or heteroaromatic ring systems, in particular radicals derived from: benzene, naphthalene, anthracene, benzanthracene, phenanthrene, pyrene,
Perylene, fluoranthene, tetracene, pentacene, benzopyrene, biphenyl, idobenzene, terphenyl, fluorene, spirobifluorene, dihydrophenanthrene, dibenzenesHydropyrene, tetrahydropyrene, cis-or trans-indenofluorene, cis-or trans-indenocarbazole, cis-or trans-indolocarbazole, triindene, isotridendene, spirotriindene, spiroisotridendene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo [5,6 ] benzo]Quinoline, benzo [6,7 ]]Quinoline, benzo [7,8 ]]Quinoline, phenothiazine, phenoxazine, pyrazole, indazole, imidazole, benzimidazole, naphthoimidazole, phenanthroimidazole, pyridoimidazole, pyrazinoimidazole, quinoxaloimidazole, oxazole, benzoxazole, naphthooxazole, anthraoxazole, phenanthroixazole, isoxazole, 1, 2-thiazole, 1, 3-thiazole, benzothiazole, pyridazine, hexaazatriphenylene, benzopyridazine, pyrimidine, benzopyrimidine, quinoxaline, 1, 5-diaza-thracene, 2, 7-diaza, 2, 3-diaza-pyrene, 1, 6-diaza-pyrene, 1, 8-diaza-pyrene, 4,5,9, 10-tetraazaperylene, pyrazine, phenazine, phenoxazine, phenothiazine, fluorescent red ring, naphthyridine, azacarbazole, benzocarbazine, carboline, phenanthroline, 1,2, 3-triazole, 1,2, 4-triazole, benzotriazole, 1,2, 3-oxadiazole, 1,2, 4-oxadiazole, 1,2, 5-oxadiazole, 1,3, 4-oxadiazole, 1,2, 3-thiadiazole, 1,2, 4-thiadiazole, 1,2, 5-thiadiazole, 1,3, 4-thiadiazole, 1,3, 5-triazine, 1,2, 4-triazine, 1,2, 3-triazine, tetrazole, 1,2,4, 5-tetrazine, 1,2,3, 4-tetrazine, 1,2,3, 5-tetrazine, purine, pteridine, indolizine, and benzothiadiazole, or a group derived from a combination of these systems.
Further, said T1Represents S;
further, said R1～R5Same or different, selected from hydrogen, deuterium, having C1～C40The linear alkyl group, the aromatic ring system or the heteroaromatic ring system having 5 to 60 carbon atoms, R1～R5Each of which may be substituted by one or more groups R, and wherein two or more adjacent substituent groups may optionally be joined or fused to form a mono-or polycyclic aliphatic, aromatic or heteroaromatic ring system;
further, theAr1Selected from aromatic or heteroaromatic ring systems having 5 to 60 carbon atoms, which ring systems may be substituted by one or more radicals R.
Further, the indole derivatives mainly include the structures shown in the following formulas (1) to (5):
r and Ar1Have the same meanings as defined above.
Furthermore, the indole derivative mainly comprises the following structures CJHL 239-CJHL 421:
an application of the indole derivative in materials for organic elements.
Further, the indole derivative is a material for an organic electroluminescent element, a material for an organic field effect transistor, or a material for an organic thin film solar cell.
Further, the indole derivative is applied to a luminescent layer material, a hole transport/hole barrier layer material or an encapsulation layer material.
An organic electroluminescent element comprising a first electrode, a second electrode and a plurality of organic layers disposed between the first electrode and the second electrode, at least one of the organic layers comprising 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 also comprise further layers, for example in each case one or more hole-injecting layers, hole-transporting layers, hole-blocking layers, electron-transporting layers, electron-injecting layers, exciton-blocking layers, electron-blocking layers and/or charge-generating layers. An intermediate layer having, for example, exciton blocking function can likewise be introduced between the two light-emitting layers. However, it should be noted that each of these layers need not be present. The organic electroluminescent device described herein may include one light emitting layer, or it may include a plurality of 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 light-emitting layers, wherein the three layers can exhibit blue, green and red light emission. If more than one light-emitting layer is present, at least one of these layers comprises the indole derivatives of the invention according to the invention.
In the other layers of the organic electroluminescent element according to the invention, in particular in the hole transport layer and in the hole blocking layer and the thin-film encapsulation layer, all materials can be used in the manner generally used according to the prior art. The person skilled in the art will thus be able to use all materials known for organic electroluminescent elements in combination with the light-emitting layer according to the invention without inventive effort.
Preference is furthermore given to organic electroluminescent elements in which one or more layers are applied by means of a sublimation process in which the temperature in a vacuum sublimation apparatus is below 10-5Pa, preferably less than 10-6Pa is applied by vapor deposition. However, the initial pressure may also be even lower, e.g. below 10-7Pa。
Preference is likewise given to 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, where 10-5The material is applied under a pressure between Pa and 1 Pa. A particular example of this method is the organic vapour jet printing method, in which the material is applied directly through a nozzle and is therefore structured.
Preference is furthermore given to organic electroluminescent elements in which one or more layers are produced from solution, for example by spin coating, or by means of any desired printing method, for example screen printing, flexographic printing, offset printing, photoinitiated thermal imaging, thermal transfer, ink-jet printing or nozzle printing. Soluble compounds, for example, are obtained by appropriate substitution of the compounds of formula (I) of the present invention. These methods are also particularly suitable for oligomers, dendrimers and polymers. Furthermore, hybrid methods are possible, in which, for example, one or more layers are applied from solution and one or more further layers are applied by vapor deposition.
Further, the organic layer may further include one or more selected from 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 light refraction layer.
The organic electroluminescent element of the present invention may be either a top emission light element or a bottom emission light element. The structure and the production method of the organic electroluminescent element of the present invention are not limited. The organic electroluminescent element prepared by the compound can reduce the starting voltage and improve the luminous efficiency and brightness.
A display device includes the organic electroluminescent element.
An illumination device comprising 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 devices 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 an organic electroluminescent element of the present invention can be used as a host material. In this case, the material for an organic electroluminescent element of the present invention may contain another compound as a dopant.
The material for an organic electroluminescent element 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, an encapsulation layer, or a photorefractive layer.
Compared with the prior art, the invention has the beneficial effects that: the indole derivative has higher triplet state energy level and high glass transition temperature, is suitable for being used as a material for an organic electroluminescent element, and the material for the organic electroluminescent element containing the indole derivative has the characteristics of low starting voltage, high luminous efficiency and high brightness. The indole derivative of the present invention has excellent thermal stability and film-forming properties, and can be used for a material for an organic electroluminescent element, a display device, and a lighting device, and can prolong the service life thereof, thereby reducing the production cost of the material for an organic electroluminescent element, the display device, and the lighting device.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the embodiments or the prior art will be briefly described below, it is obvious that the drawings in the following description are only some embodiments of the present invention, and for those skilled in the art, other drawings can be obtained according to the drawings without creative efforts.
FIG. 1 is a schematic view of a bottom emission example of an organic electroluminescent device of the present invention;
fig. 2 is a schematic view of one example of top emission of the organic electroluminescent device of the present invention.
Reference numerals
1-substrate, 2-anode, 3-hole injection layer, 4-hole transport/electron blocking layer, 5-luminescent layer, 6-hole transport/electron transport layer, 7-electron injection layer and 8-cathode.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the technical solutions of the present invention will be described in detail below. It is to be understood that the described embodiments are merely exemplary of the invention, and not restrictive of the full scope of the invention. All other embodiments, which can be derived by a person skilled in the art from the examples given herein without any inventive step, are within the scope of the present invention.
The following examples illustrate the performance of OLED materials and devices as follows:
OLED element performance detection conditions:
luminance and chromaticity coordinates: testing with a photosresearch PR-715 spectrum scanner;
current density and lighting voltage: testing using a digital source table Keithley 2420;
power efficiency: tested using NEWPORT 1931-C;
and (3) life test: an LTS-1004AC life test apparatus was used.
Example 1
Preparation of intermediate a 1:
mixing 56.0mmol of 3-nitrobenzothiophene, 73.0mmol of 4-hydroxy carbazole, 28.0mmol of anhydrous potassium carbonate and 200mL of anhydrous ethanol, heating, refluxing, stirring, reacting for 24 hours, cooling to room temperature, concentrating under reduced pressure, and separating and purifying by a silica gel column to obtain an intermediate A1 which is yellow solid with the yield of 69%.
The following compounds were prepared in a similar manner to the synthesis described above:
example 2
The preparation method of the intermediate A5 comprises the following steps:
the first step is as follows: preparation of Compound Int-1
0.15mol of 2, 6-dimethoxyphenylboronic acid and 0.10mol of 2, 3-dibromobenzothiophene are dissolved in 150mL of 1, 4-dioxane and 30mL of water, and 0.40mol of anhydrous potassium carbonate and 1.0g of Pd (PPh) are added under nitrogen protection3)4And (3) heating the catalyst to 90 ℃, stirring and reacting for 12 hours, cooling to room temperature, adding 50mL of water for dilution, extracting with ethyl acetate, collecting an organic phase, drying, filtering, concentrating the filtrate under reduced pressure to dryness, and separating and purifying by using a silica gel column to obtain a compound Int-1 with the yield of 87%.
The second step is that: preparation of Compound Int-2
Dissolving 55.0mmol of Int-1 in 150mL of dry dichloromethane, cooling to 0 ℃ under the protection of nitrogen, dropwise adding a solution of 165.0mmol of boron tribromide dissolved in dichloromethane, stirring for reaction for 2 hours, heating to room temperature, stirring for reaction for 2 hours, adding 200mL of saturated aqueous ammonium chloride solution, filtering, separating an organic phase from a filtrate, drying, filtering, concentrating the filtrate under reduced pressure to dryness, and separating and purifying by using a silica gel column to obtain the compound Int-2 with the yield of 93%.
The third step: preparation of Compound Int-3
Dissolving 40.0mmol of intermediate Int-2 in 80mL of DMF, adding 4.0mmol of cuprous iodide, 8.0mmol of 1, 10-phenanthroline and 80.0mmol of anhydrous potassium carbonate under the protection of nitrogen, heating to 90 ℃, stirring for reaction for 15 minutes, cooling to room temperature, adding 150mL of 2N diluted hydrochloric acid aqueous solution, extracting with ethyl acetate, washing an organic phase with saturated salt water, washing with water, drying, filtering, concentrating the filtrate under reduced pressure to dryness, and separating and purifying with a silica gel column to obtain a compound Int-3 with the yield of 96%.
The fourth step: preparation of Compound Int-4
Dissolving 40.0mmol of intermediate Int-3 and 80.0mmol of pyridine in 100mL of dichloromethane, cooling to 0 ℃ under the protection of nitrogen, dropwise adding 48.0mmol of trifluoromethanesulfonic anhydride, heating to room temperature, stirring for reaction for 10 hours, adding 50mL of 1N dilute hydrochloric acid aqueous solution, extracting with dichloromethane, washing an organic phase with water, drying, filtering, concentrating a filtrate under reduced pressure to dryness, and separating and purifying by using a silica gel column to obtain the compound Int-4 with the yield of 94%.
The fifth step: preparation of Compound Int-5
50.0mmol of intermediate Int-4 and 60.0mmol of pinacol o-nitrobenzoate borate are dissolved in 80mL of toluene, and 0.1mol of anhydrous sodium carbonate and 0.5mmol of Pd (PPh) are added under nitrogen protection3)4Heating, refluxing and stirring the catalyst, 30mL of ethanol and 30mL of water for reaction for 15 hours, adding 50mL of water for dilution, taking the mixture by using ethyl acetate, drying the organic phase, filtering, concentrating the filtrate under reduced pressure to dryness, and separating and purifying the filtrate by using a silica gel column to obtain a compound Int-5 with the yield of 87%.
And a sixth step: preparation of intermediate A5
50.0mmol of intermediate Int-5 and 150.0mmol of triphenylphosphine are mixed, heated to 150 ℃ under the protection of nitrogen, stirred and reacted for 2 hours, cooled to 100 ℃, added with 150mL of toluene, cooled to room temperature, filtered, and the filter cake is separated and purified by a silica gel column to obtain intermediate A5 with the yield of 68%.
Example 3
The preparation method of the intermediate A6 comprises the following steps:
the first step is as follows: preparation of Compound Int-6
Under the protection of nitrogen, 50.0mmol of Int-4, 60.0mmol of o-chloroaniline, 75.0mmol of sodium tert-butoxide and 0.5mmol of Pd2(dba)3The catalyst was dissolved in 80mL of toluene, 1.0mmol of Xanphos (CAS:161265-03-8) was added, the reaction was stirred at 100 ℃ for 12 hours, cooled to room temperature, diluted with 50mL of water, extracted with ethyl acetate, the organic phase was collected, dried, filtered, the filtrate was concentrated to dryness under reduced pressure, and separated and purified by silica gel column to give compound Int-6 with 88% yield.
The second step is that: preparation of intermediate A6
Under the protection of nitrogen, 50.0mmol of Int-6, 75.0mmol of sodium tert-butoxide and 0.5mmol of palladium acetate are dissolved in 80mL of xylene, 1.0mmol of Xanphos (CAS:161265-03-8) is added, the mixture is stirred and reacted at the temperature of 110 ℃ for 12 hours, the mixture is cooled to room temperature, 50mL of water is added for dilution, extraction is carried out by ethyl acetate, an organic phase is collected, drying and filtration are carried out, filtrate is concentrated under reduced pressure to dryness, and the filtrate is separated and purified by a silica gel column to obtain an intermediate A6 with the yield of 76%.
Example 4
Preparation of compound CJHL 280:
10.0mmol of intermediate A1 is dissolved in 80mL of dry THF, the temperature is reduced to 0 ℃ by an ice water bath under the protection of nitrogen, 11.0mmol of 65% sodium hydride solid is added, stirring reaction is carried out for 1 hour, 11.0mmol of 2-chloro-4, 6-diphenyl-1, 3, 5-triazine is added, stirring reaction is carried out for 24 hours, 50mL of water is added for dilution, extraction is carried out by ethyl acetate, an organic phase is collected, drying and filtration are carried out, filtrate is concentrated under reduced pressure to be dry, and separation and purification are carried out by a silica gel column to obtain a compound CJHL280, a yellow solid with the yield of 63%.
MS and of compound CJHL2801The HNMR test results are as follows:
MS(MALDI-TOF)：m/z 545.1452[M+H]+；1HNMR(δ、CDCl3)：9.16～9.14(m,1H)；8.38～8.35(m,5H)；8.28～8.26(d,1H)；8.04～7.98(m,3H)；7.56～7.48(m,8H)；7.41～7.36(m,2H)。
the following compounds were prepared in a similar manner to the synthesis described above:
example 5
Preparation of compound CJHL 381:
15.0mmol of intermediate A5 was dissolved in 80mL of dry toluene, 16.5mmol of 2- (3-bromophenyl) -4, 6-diphenyl-1, 3, 5-triazine (CAS:864377-31-1) and 22.5mmol of sodium tert-butoxide were added under nitrogen, and 0.1mmol of Pd was added2(dba)3CHCl3And 0.02mL of 10% toluene solution of phosphorus tri-tert-butyl, heating to 100 ℃, stirring for reaction for 15 hours, cooling to room temperature, adding 50mL of water for dilution, extracting with ethyl acetate, collecting an organic phase, drying, filtering, concentrating the filtrate under reduced pressure to dryness, and separating and purifying by using a silica gel column to obtain the compound CJHL381, a yellow solid with the yield of 78%.
MS and of compound CJHL3811The HNMR test results are as follows:
MS(MALDI-TOF)：m/z 621.1763[M+H]+；1HNMR(δ、CDCl3)：8.81～8.78(m,4H)；8.38～8.36(m,1H)；8.20(s,1H)；7.96～7.91(m,3H)；7.72～7.70(d,1H)；7.62～7.39(m,12H)；7.34～7.32(m,2H)。
the following compounds were prepared in a similar manner to the synthesis described above:
preparation of organic electroluminescent element
Comparative example 1
The following compound a was used as a green host material, the following compound B was used as a green dopant, compound C was used as a hole injection material, compound D was used as a hole transport material, compound E was used as a red dopant, compound F was used as a red dopant, compound G was used as an electron transport dopant, and LiQ was used as an electron transport host material.
Compound C
/D
/A+B(5％)
/LiQ+G(50％)
/LiF
Al (2nm) was deposited on ITO glass by an EL deposition machine manufactured by DOV to produce a green light element, and an organic electroluminescent element as green light was produced.
Will be the chemical formula C
/D
/E+F(3％)
/LiQ+G(50％)
/LiF
Al (2nm) was deposited on ITO glass by an EL deposition machine manufactured by DOV to produce a red light element, and an organic electroluminescent element was produced as red light.
Test example 1
The green organic electroluminescent element was prepared according to the method of comparative example 1 by replacing compound a with the compounds CJHL239 to CJHL421 of the present invention.
The results of measuring the properties of the obtained green organic electroluminescent element are shown in Table 1, in which the driving voltage (V), the current efficiency (LE), the color Coordinate (CIE), the full width at half maximum (FWHM) were 10mA/cm in current density of the element2Conditions were obtained and the voltage, LE, FWHM and LT 90% were normalized to the reference.
TABLE 1 Green light element Performance test results
As is clear from Table 1, the green light emitting device produced from the organic material of the present invention has a low driving voltage, a high current efficiency, a good color purity, and an initial emission luminance of 2000cd/cm in comparison with the device produced in comparative example 12Under the initial conditions, the LT 90% lifetime of the element using the compound of the present invention as a green host material was greatly improved.
The properties of only some of the compounds in CJHL 239-CJHL 421 are listed in Table 1, and the properties of other compounds are substantially identical to the structures of the compounds listed in the Table, and are not listed due to space limitation.
A red light member was produced according to the method of comparative example 1, wherein the foregoing was mixedIn addition to replacing compound E with the compounds CJHL239 to CJHL421 of the invention, ITO/C
/D
/[ inventive Compounds CJHL239 to CJHL421]+F(3％)
/LiQ+G(50％)
/LiF
/Al(2nm)。
The results of measuring the properties of the obtained element are shown in Table 2, in which the driving voltage (V), the current efficiency (LE), the color Coordinate (CIE), and the full width at half maximum (FWHM) were measured at a current density of 10mA/cm2Conditions were obtained and the voltage, LE, FWHM and LT 90% were normalized to the reference.
TABLE 2 Red light element Performance test results
As can be seen from the performance test results of the red light device in Table 2, the device prepared from the organic material of the present invention has significantly lower driving voltage, high current efficiency and good color purity of light emission compared to the red light device prepared in comparative example 1. At an initial luminance of 2000cd/cm2Under the initial conditions, the LT 90% lifetime of the element using the compound of the present invention as a red host material was significantly improved.
The properties of only some of the compounds in CJHL 239-CJHL 421 are listed in Table 2, and the properties of other compounds are substantially identical to the structures of the compounds listed in the Table, and are not listed due to space limitation.
As shown in fig. 1 and 2, which are a schematic view of a bottom emission example of the organic electroluminescent device of the present invention and a schematic view of a top emission example of the organic electroluminescent device, respectively, the indole derivative prepared according to the present invention is contained in the light-emitting layer 5.
The above description is only for the specific embodiments of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art can easily conceive of the changes or substitutions within the technical scope of the present invention, and all the changes or substitutions should be covered within the scope of the present invention. Therefore, the protection scope of the present invention shall be subject to the protection scope of the appended claims.
Claims (10)
1. An indole derivative, wherein the structure of the indole derivative is shown as formula (I):
wherein any two adjacent groups W1、W2、W3、W4Represents a group of the following formula (II),
wherein Z, identically or differently at each occurrence, denotes CR5Or N, and ^ indicates the corresponding adjacent group W in formula I1And W2、W2And W3Or W3And W4；
T1Representation O, S, NAr2Or CR6R7；
R1～R7Same or different, selected from hydrogen, deuterium, having C1～C40Straight chain alkyl of (2) having C1～C40Linear heteroalkyl group of (A) having C3～C40A branched or cyclic alkyl group having C3～C40Is branched chain ofOr a cyclic heteroalkyl group having C2～C40Alkenyl or alkynyl group of (A), an aromatic ring system or a heteroaromatic ring system having 5 to 60 carbon atoms, R1～R7Each of which may be substituted by one or more groups R, and wherein two or more adjacent substituent groups may optionally be joined or fused to form a mono-or polycyclic aliphatic, aromatic or heteroaromatic ring system;
Ar1、Ar2same or different, selected from the group consisting of having C1～C40Straight chain alkyl of (2) having C1～C40Linear heteroalkyl group of (A) having C3～C40A branched or cyclic alkyl group having C3～C40A branched or cyclic heteroalkyl group of (A) having C2～C40Alkenyl or alkynyl groups of (a), aromatic or heteroaromatic ring systems having 5 to 60 carbon atoms, which ring systems may be substituted by one or more radicals R;
each occurrence of R is the same or different and is selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a nitrile group, a nitro group, and N (Ar)3)2、N(R12)2、C(＝O)Ar3、C(＝O)R8、P(＝O)(Ar3)2Having a structure of C1～C40Straight chain alkyl of (2) having C1～C40Linear heteroalkyl group of (A) having C3～C40A branched or cyclic alkyl group having C3～C40A branched or cyclic heteroalkyl group of (A) having C2～C40Alkenyl or alkynyl groups of (A), aromatic or heteroaromatic ring systems having from 5 to 80 carbon atoms, aryloxy or heteroaryloxy groups having from 5 to 60 carbon atoms, each of the R groups being optionally substituted by one or more radicals R8Substituted, or combinations of these systems, wherein one or more non-adjacent-CH2The radicals may be substituted by R8C＝CR8、C≡C、Si(R8)2、Ge(R8)2、Sn(R8)2、C＝O、C＝S、C＝Se、C＝NR8、P(＝O)(R8)、SO、SO2、NR8O, S or CONR8Instead of, and itWherein one or more hydrogen atoms are replaced by deuterium atoms, halogen atoms, nitrile groups or nitro groups, wherein two or more adjacent substituents R may optionally be joined or fused to form a mono-or polycyclic, aliphatic, aromatic or heteroaromatic ring system which may be interrupted by one or more radicals R8Substitution;
R8each occurrence of the same or different is selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a nitrile group, a nitro group, and N (Ar)3)2、N(R9)2、C(＝O)Ar3、C(＝O)R9、P(＝O)(Ar3)2Having a structure of C1～C40Straight chain alkyl of (2) having C1～C40Linear heteroalkyl group of (A) having C3～C40A branched or cyclic alkyl group having C3～C40A branched or cyclic heteroalkyl group of (A) having C2～C40One of alkenyl or alkynyl, aromatic or heteroaromatic ring system having 5 to 60 carbon atoms, aryloxy or heteroaryloxy having 5 to 60 carbon atoms, R8Each radical in (a) may be substituted by one or more radicals R9Substituted, or combinations of these systems, wherein one or more non-adjacent-CH2The radicals may be substituted by R9C＝CR9、C≡C、Si(R9)2、Ge(R9)2、Sn(R9)2、C＝O、C＝S、C＝Se、C＝NR9、P(＝O)(R9)、SO、SO2、NR9O, S or CONR9And wherein one or more hydrogen atoms may be replaced by deuterium atoms, halogen atoms, nitrile groups or nitro groups, wherein two or more adjacent substituents R8Aliphatic, aromatic or heteroaromatic ring systems which may optionally be joined or fused to form a single ring or multiple rings and which may be interrupted by one or more radicals R9Substitution;
Ar3identical or different at each occurrence and selected from aromatic or heteroaromatic ring systems having from 5 to 30 carbon atoms which may be substituted by one or more nonaromatic radicals R9Substitution; two groups Ar here bonded to the same nitrogen or phosphorus atom3Or by a single bond orIs selected from N (R)9)、C(R9)2Oxygen or sulfur bridging groups;
R9selected from hydrogen atom, deuterium atom, fluorine atom, nitrile group, having C1～C20An aliphatic hydrocarbon group, an aromatic ring or a heteroaromatic ring system having 5 to 30 carbon atoms, wherein R9Wherein one or more hydrogen atoms may be replaced by deuterium atoms, halogen atoms, or nitrile groups, wherein two or more adjacent substituents R9They can form mono-or polycyclic aliphatic, aromatic or heteroaromatic ring systems with one another.
2. The indole derivative of claim 1, wherein T is1Represents S; r1～R5Same or different, selected from hydrogen, deuterium, having C1～C40The linear alkyl group, the aromatic ring system or the heteroaromatic ring system having 5 to 60 carbon atoms, R1～R5Each of which may be substituted by one or more groups R, and wherein two or more adjacent substituent groups may optionally be joined or fused to form a mono-or polycyclic aliphatic, aromatic or heteroaromatic ring system;
ar is1Selected from aromatic or heteroaromatic ring systems having 5 to 60 carbon atoms, which ring systems may be substituted by one or more radicals R.
3. The indole derivative according to claim 1 or 2, wherein the indole derivative has a structure represented by the following formulae (1) to (5):
r and Ar1Has the same meaning as defined in claim 1.
4. The indole derivative according to any one of claims 1 to 3, wherein the indole derivative has the following structure CJHL 239-CJHL 421:
5. use of the indole derivative according to any one of claims 1 to 4 as a material for organic devices.
6. The use according to claim 5, wherein the indole derivative is a material for an organic electroluminescent device, a material for an organic field effect transistor, or a material for an organic thin film solar cell.
7. Use according to claim 6, wherein the indole derivative is used in a light-emitting layer material, a hole transporting/hole blocking layer material or an encapsulating layer material.
8. An organic electroluminescent element comprising a first electrode, a second electrode, and a plurality of organic layers disposed between the first electrode and the second electrode, wherein at least one of the organic layers comprises the indole derivative according to any one of claims 1 to 4.
9. A display device comprising the organic electroluminescent element according to claim 8.
10. A lighting device comprising the organic electroluminescent element according to claim 8.
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