CN109942588A - Benzazolyl compounds and preparation method thereof and organic luminescent device comprising the compound - Google Patents
Benzazolyl compounds and preparation method thereof and organic luminescent device comprising the compound Download PDFInfo
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- CN109942588A CN109942588A CN201910323368.4A CN201910323368A CN109942588A CN 109942588 A CN109942588 A CN 109942588A CN 201910323368 A CN201910323368 A CN 201910323368A CN 109942588 A CN109942588 A CN 109942588A
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- -1 Benzazolyl compounds Chemical class 0.000 title claims abstract description 63
- 238000002360 preparation method Methods 0.000 title claims abstract description 38
- 150000001875 compounds Chemical class 0.000 title claims abstract description 17
- 239000000126 substance Substances 0.000 claims abstract description 11
- 238000004519 manufacturing process Methods 0.000 claims abstract description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 45
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 35
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 35
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 35
- 239000011368 organic material Substances 0.000 claims description 33
- 238000002347 injection Methods 0.000 claims description 27
- 239000007924 injection Substances 0.000 claims description 27
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 230000005525 hole transport Effects 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 229940125904 compound 1 Drugs 0.000 claims description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims description 12
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 239000000243 solution Substances 0.000 claims description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- 238000003756 stirring Methods 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 6
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 239000011259 mixed solution Substances 0.000 claims description 5
- 239000012074 organic phase Substances 0.000 claims description 5
- 150000004982 aromatic amines Chemical class 0.000 claims description 4
- 230000000903 blocking effect Effects 0.000 claims description 4
- 150000002894 organic compounds Chemical class 0.000 claims description 4
- 125000003367 polycyclic group Chemical group 0.000 claims description 4
- 239000002994 raw material Substances 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 claims description 3
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000001769 aryl amino group Chemical group 0.000 claims description 3
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 3
- 125000005110 aryl thio group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 229910052805 deuterium Inorganic materials 0.000 claims description 3
- 239000012153 distilled water Substances 0.000 claims description 3
- 239000002019 doping agent Substances 0.000 claims description 3
- 125000004185 ester group Chemical group 0.000 claims description 3
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000005462 imide group Chemical group 0.000 claims description 3
- 125000002560 nitrile group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims description 3
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims description 3
- 239000003208 petroleum Substances 0.000 claims description 3
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- 125000006743 (C1-C60) alkyl group Chemical group 0.000 claims description 2
- 125000006744 (C2-C60) alkenyl group Chemical group 0.000 claims description 2
- 125000006818 (C3-C60) cycloalkyl group Chemical group 0.000 claims description 2
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims description 2
- UXKCLTPQRBKROC-UHFFFAOYSA-N C(C)(C)C1=C(C(=CC(=C1)C(C)C)C(C)C)C1=CC=CC=C1.[P] Chemical group C(C)(C)C1=C(C(=CC(=C1)C(C)C)C(C)C)C1=CC=CC=C1.[P] UXKCLTPQRBKROC-UHFFFAOYSA-N 0.000 claims description 2
- 125000005264 aryl amine group Chemical group 0.000 claims description 2
- 125000000732 arylene group Chemical group 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 150000002736 metal compounds Chemical class 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 59
- 239000010410 layer Substances 0.000 description 98
- 125000001424 substituent group Chemical group 0.000 description 16
- 230000015572 biosynthetic process Effects 0.000 description 13
- 238000000034 method Methods 0.000 description 13
- 238000003786 synthesis reaction Methods 0.000 description 13
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 12
- 230000032258 transport Effects 0.000 description 10
- 239000007858 starting material Substances 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 6
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 4
- VIJSPAIQWVPKQZ-BLECARSGSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-acetamido-5-(diaminomethylideneamino)pentanoyl]amino]-4-methylpentanoyl]amino]-4,4-dimethylpentanoyl]amino]-4-methylpentanoyl]amino]propanoyl]amino]-5-(diaminomethylideneamino)pentanoic acid Chemical compound NC(=N)NCCC[C@@H](C(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(C)=O VIJSPAIQWVPKQZ-BLECARSGSA-N 0.000 description 4
- STBLNCCBQMHSRC-BATDWUPUSA-N (2s)-n-[(3s,4s)-5-acetyl-7-cyano-4-methyl-1-[(2-methylnaphthalen-1-yl)methyl]-2-oxo-3,4-dihydro-1,5-benzodiazepin-3-yl]-2-(methylamino)propanamide Chemical compound O=C1[C@@H](NC(=O)[C@H](C)NC)[C@H](C)N(C(C)=O)C2=CC(C#N)=CC=C2N1CC1=C(C)C=CC2=CC=CC=C12 STBLNCCBQMHSRC-BATDWUPUSA-N 0.000 description 4
- VUEGYUOUAAVYAS-JGGQBBKZSA-N (6ar,9s,10ar)-9-(dimethylsulfamoylamino)-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline Chemical compound C1=CC([C@H]2C[C@@H](CN(C)[C@@H]2C2)NS(=O)(=O)N(C)C)=C3C2=CNC3=C1 VUEGYUOUAAVYAS-JGGQBBKZSA-N 0.000 description 4
- PYRKKGOKRMZEIT-UHFFFAOYSA-N 2-[6-(2-cyclopropylethoxy)-9-(2-hydroxy-2-methylpropyl)-1h-phenanthro[9,10-d]imidazol-2-yl]-5-fluorobenzene-1,3-dicarbonitrile Chemical compound C1=C2C3=CC(CC(C)(O)C)=CC=C3C=3NC(C=4C(=CC(F)=CC=4C#N)C#N)=NC=3C2=CC=C1OCCC1CC1 PYRKKGOKRMZEIT-UHFFFAOYSA-N 0.000 description 4
- JQUCWIWWWKZNCS-LESHARBVSA-N C(C1=CC=CC=C1)(=O)NC=1SC[C@H]2[C@@](N1)(CO[C@H](C2)C)C=2SC=C(N2)NC(=O)C2=NC=C(C=C2)OC(F)F Chemical compound C(C1=CC=CC=C1)(=O)NC=1SC[C@H]2[C@@](N1)(CO[C@H](C2)C)C=2SC=C(N2)NC(=O)C2=NC=C(C=C2)OC(F)F JQUCWIWWWKZNCS-LESHARBVSA-N 0.000 description 4
- OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- SPXSEZMVRJLHQG-XMMPIXPASA-N [(2R)-1-[[4-[(3-phenylmethoxyphenoxy)methyl]phenyl]methyl]pyrrolidin-2-yl]methanol Chemical compound C(C1=CC=CC=C1)OC=1C=C(OCC2=CC=C(CN3[C@H](CCC3)CO)C=C2)C=CC=1 SPXSEZMVRJLHQG-XMMPIXPASA-N 0.000 description 4
- PSLUFJFHTBIXMW-WYEYVKMPSA-N [(3r,4ar,5s,6s,6as,10s,10ar,10bs)-3-ethenyl-10,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-6-(2-pyridin-2-ylethylcarbamoyloxy)-5,6,6a,8,9,10-hexahydro-2h-benzo[f]chromen-5-yl] acetate Chemical compound O([C@@H]1[C@@H]([C@]2(O[C@](C)(CC(=O)[C@]2(O)[C@@]2(C)[C@@H](O)CCC(C)(C)[C@@H]21)C=C)C)OC(=O)C)C(=O)NCCC1=CC=CC=N1 PSLUFJFHTBIXMW-WYEYVKMPSA-N 0.000 description 4
- 229940125758 compound 15 Drugs 0.000 description 4
- 229940126086 compound 21 Drugs 0.000 description 4
- 229940125878 compound 36 Drugs 0.000 description 4
- 229940127271 compound 49 Drugs 0.000 description 4
- GWNFQAKCJYEJEW-UHFFFAOYSA-N ethyl 3-[8-[[4-methyl-5-[(3-methyl-4-oxophthalazin-1-yl)methyl]-1,2,4-triazol-3-yl]sulfanyl]octanoylamino]benzoate Chemical compound CCOC(=O)C1=CC(NC(=O)CCCCCCCSC2=NN=C(CC3=NN(C)C(=O)C4=CC=CC=C34)N2C)=CC=C1 GWNFQAKCJYEJEW-UHFFFAOYSA-N 0.000 description 4
- 238000004770 highest occupied molecular orbital Methods 0.000 description 4
- 239000010405 anode material Substances 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 238000007738 vacuum evaporation Methods 0.000 description 3
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- 239000010406 cathode material Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- 239000011135 tin Substances 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 1
- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical group N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 1
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 241001082241 Lythrum hyssopifolia Species 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N SnO2 Inorganic materials O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 125000004062 acenaphthenyl group Chemical group C1(CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000004653 anthracenylene group Chemical group 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 125000000707 boryl group Chemical group B* 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000002322 conducting polymer Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
- 125000005303 dithiazolyl group Chemical group S1SNC(=C1)* 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 125000005567 fluorenylene group Chemical group 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- AILKHAQXUAOOFU-UHFFFAOYSA-N hexanenitrile Chemical compound CCCCCC#N AILKHAQXUAOOFU-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000003933 pentacenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C12)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000005562 phenanthrylene group Chemical group 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000005548 pyrenylene group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000005551 pyridylene group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 150000003413 spiro compounds Chemical class 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000006836 terphenylene group Chemical group 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000005558 triazinylene group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Electroluminescent Light Sources (AREA)
Abstract
The present invention relates to luminescent material technical fields, and in particular to a kind of benzazolyl compounds and preparation method thereof and the organic luminescent device comprising the compound, the structural formula of the benzazolyl compounds as described in chemical formula 1:
Description
Technical Field
The invention relates to the technical field of luminescent materials, in particular to an indole compound, a preparation method thereof and an organic luminescent device containing the indole compound.
Background
The organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode, a cathode, and an organic material layer therebetween.
The organic material layer is formed as a multi-layered structure formed of different materials to improve efficiency and stability of the organic light emitting device, and may be formed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, or the like. In such an organic light emitting device structure, when a voltage is applied between two electrodes, holes and electrons are injected from an anode and a cathode into an organic material layer, respectively, excitons are formed when the injected holes and electrons meet, and light is emitted when the excitons return to a ground state.
The material types and the collocation forms have the characteristics of richness and diversity. In addition, for the collocation of OLED devices with different structures, the used photoelectric functional material has stronger selectivity, and the performance of the same material in the devices with different structures can be completely different. Therefore, aiming at the industrial application requirements of the current OLED device and the requirements of different functional film layers and photoelectric characteristics of the OLED device, a more suitable OLED functional material or material combination with higher performance needs to be selected to realize the comprehensive characteristics of high efficiency, long service life and low voltage of the device. In terms of the actual demand of the current OLED display lighting industry, the development of the current OLED material is far from enough, and lags behind the requirements of panel manufacturing enterprises, and it is very important to develop a higher-performance organic functional material as a material enterprise.
Disclosure of Invention
The present invention aims to provide an indole compound, a method for preparing the same, and an organic light emitting device comprising the same.
In order to achieve the above purpose, the technical scheme of the invention is as follows:
the invention provides an indole compound, which has a structural formula shown in a chemical formula 1:
wherein,
ar is a substituted or unsubstituted aryl, substituted or unsubstituted arylamine, or substituted or unsubstituted heterocyclic group;
l is a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroaryl;
preferably, L are the same or different from each other and are each independently selected from one or more types of: a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted pyrenylene group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted pyrimidylene group, a substituted or unsubstituted triazinylene group, a substituted or unsubstituted quinolylene group, a substituted or unsubstituted quinazolinylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted divalent dibenzothiophenyl group;
m is an integer of 0-2; n is an integer of 0 or more;
R1to R7The same or different from each other, and each independently is hydrogen, deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted alkylsulfonyl group, a substituted or unsubstituted arylsulfonyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aralkenyl group, a substituted or unsubstituted alkylaryl group, a substituted or unsubstituted aralkylamino group, a substituted or unsubstituted heteroarylamino group, a substituted or unsubstituted arylamino group, A substituted or unsubstituted aryl phosphine group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group;
x is-O-, -S-, -SO2-、-C(R10)(R11)-、-N(R12)-、-Si(R13)(R14)-、-Sn(R15)(R16) -or-Ge (R)17)(R18)-；
R8～R18Is substituted or unsubstituted C1-C60 alkyl, C3-C60 cycloalkyl, substituted or unsubstituted C2-C60 alkenyl, C3-C60 cycloalkenyl, substituted or unsubstituted C3-C60 alkynyl or C3-C60 cycloalkynyl; substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 aralkylamino, substituted or unsubstituted C6-C60 heteroarylamino, substituted or unsubstituted C6-C60 arylamino, or C6-C60 heteroaryl.
In the present invention, the term "substituted or unsubstituted" means substituted with one or more substituents selected from the group consisting of: deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amine group, a phosphine oxide group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkylsulfonyl group, an arylsulfonyl group, a silyl group, a boryl group, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, an aralkyl group, an aralkenyl group, an alkylaryl group, an alkylamino group, an aralkylamino group, a heteroarylamino group, an arylamino group, an arylphosphino group, and a heterocyclic group; or substituted with a substituent linked to two or more of the above exemplified substituents, or unsubstituted. For example, a substituent group "to which two or more substituent groups are attached may include a biphenyl group. In other words, a biphenyl group may be an aryl group, or may be interpreted as a substituent with two phenyl groups attached.
In the present invention, the adjacent "group may mean a substituent which replaces an atom directly connected to an atom substituted with the corresponding substituent, a substituent which is disposed closest to the corresponding substituent in space, or another substituent which replaces an atom substituted with the corresponding substituent. The meaning of forming a ring by combining with an adjacent group is to form a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic hydrocarbon ring, a substituted or unsubstituted aliphatic heterocyclic ring, a substituted or unsubstituted aromatic heterocyclic ring, or a condensed ring thereof by combining with an adjacent group.
In the present invention, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the number of carbon atoms of the aryl group is from 6 to 40. According to another embodiment, the number of carbon atoms of the aryl group is from 6 to 20. Examples of the monocyclic aryl group may include phenyl, biphenyl, terphenyl, and the like, but are not limited thereto. Examples of the polycyclic aryl group may include naphthyl, anthryl, phenanthryl, perylenyl, fluoranthenyl, triphenylenyl, pyrenyl, tetracenyl, pentacenyl, fluorenyl, indenyl, acenaphthenyl, benzofluorenyl, spirofluorenyl, and the like, but are not limited thereto.
In the present invention, the heterocyclic group is a heterocyclic group containing N, O, S one or more as a hetero atom, and although not particularly limited thereto, the number of carbon atoms is also preferably 2 to 60. According to one embodiment, the number of carbon atoms of the heterocyclic group is from 2 to 40. Examples of the heterocyclic group may include pyridyl, pyrrolyl, pyrimidinyl, pyridazinyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, dithiazolyl, tetrazolyl, pyranyl, thiopyranyl, pyrazinyl, oxazinyl, thiazinyl, triazinyl, tetrazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, acridinyl, xanthenyl, phenanthridinyl, naphthyridinyl, triazainenyl, indolyl, indolinyl, indolizinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, benzothiazolyl, benzimidazolyl, benzothienyl, benzofuranyl, dibenzothienyl, dibenzofuranyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, indolocarbazolyl, pyrazinopyrazinyl, pyridopyrazinyl, pyrazinopyrazinyl, benzothiazolyl, benzimidazolyl, benzothiophenyl, benzofuranyl, dibenzothienyl, dibenzofuranyl, carbazolyl, indenocarbazolyl, phenazinyl, phenanthridinyl, phenanthrolinyl, phenothiazinyl, imidazopyridine, imidazophenanthridinyl, benzimidazoloquinazolinyl, benzimidazolophenanthridinyl and the like, but are not limited thereto.
In the above technical solution, preferably, the indole compound has any one structure shown in chemical formula 2-chemical formula 6:
wherein, in chemical formulas 2 to 6, L, Ar, m, n, X and R1To R9The definition of (b) is the same as the range defined in chemical formula 1.
In the above technical scheme, it is preferable that Ar is a substituted or unsubstituted polycyclic aryl group of 6 to 40 carbon atoms, an arylamine group having 6 to 40 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 40 carbon atoms.
In the above technical solution, it is preferable that wherein- (L) n-Ar is any one selected from the following structures:
in the above technical solutions, it is most preferable that the indole compound is selected from any one of the following structures:
in the present invention, compounds having various energy band gaps can be obtained by introducing Ar- (L) m, R in the above-mentioned core structure1And R9Various substituents are introduced at positions for synthesis.
Further, by introducing various substituents to the core structure having the above structure, a compound having unique characteristics of the introduced substituents can be synthesized. For example, by introducing substituents into the core structure that are commonly used in: the hole injection layer material, the hole transport layer material, the light emitting layer material, the electron transport layer material and the electron injection layer material used for manufacturing the organic light emitting device can be synthesized into materials meeting the requirements of all organic material layers.
The invention also provides a preparation method of the indole compound, which comprises the following steps:
step 1, preparation of intermediate C
Dissolving a raw material A and a raw material B in toluene under the nitrogen atmosphere, adding sodium tert-butoxide and 2-dicyclohexyl phosphorus-2, 4, 6-triisopropyl biphenyl, adding palladium acetate, heating the reaction, stirring the reaction, cooling to room temperature after the reaction is finished, removing salt and a catalyst, concentrating the toluene, and recrystallizing by using ethanol to obtain an intermediate C; the reaction temperature is preferably 100 ℃, and the stirring time is 10 hours;
step 2, preparation of intermediate E
Dissolving the intermediate C and the intermediate D in a mixed solution of toluene and tetrahydrofuran, adding p-toluenesulfonic acid into the mixed solution, heating the obtained product, stirring for reaction, reducing the temperature to room temperature, adding distilled water and sodium carbonate into a reaction solution to neutralize the solution to be neutral, separating, extracting, concentrating an organic phase by using at least one solvent, dropwise adding the organic phase into cold ethanol, and separating out to obtain an intermediate E; the reaction temperature is preferably 50 ℃, and the stirring time is 2 hours;
step 3, preparation of compound of chemical formula 1
After dissolving the intermediate E and the intermediate F in toluene under a nitrogen atmosphere, adding sodium tert-butoxide, then adding tri-tert-butylphosphine and tris (dibenzylideneacetone) dipalladium, heating the resultant, carrying out a stirring reaction, after lowering the temperature to room temperature, filtering the resultant to remove salts, concentrating toluene, and passing the resultant through a column using dichloromethane to petroleum ether 1:5 to prepare a compound 1; the reaction temperature is preferably 100 ℃, and the stirring time is 12 hours;
the synthetic route is as follows:
wherein Y is halogen, Ar, L, m, n, X, R1To R9In accordance with the limitations in chemical formula 1.
The present invention also provides an organic light emitting device comprising: a first electrode, a second electrode, and one or more organic material layers disposed between the first electrode and the second electrode, wherein one or more of the organic material layers comprises the indole compound of the present invention;
the organic light emitting device of the present invention may be manufactured using a conventional method and materials for manufacturing an organic light emitting device, except that one or more of the organic material layers are formed using the indole compound according to the present invention.
The organic material layer of the organic light emitting device of the present invention may be formed in a single layer structure, but may also be formed in a multilayer structure in which a layer contains two or more organic material layers. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like as an organic material layer. However, the structure of the organic light emitting device is not limited thereto, and a smaller number of organic material layers may be included.
Preferably, the organic material layer includes a light emitting layer, and the light emitting layer includes the indole compound according to the present invention as a host of the light emitting layer. As one example, the compound represented by chemical formula 1 may be included as a phosphorescent host material of the light emitting layer.
It is further preferable that the organic material layer contains the indole compound according to the present invention as a host, and contains other organic compound, metal or metal compound as a dopant. As an example, the compound may be used with an iridium (Ir) based dopant.
It is preferable that the organic material layer includes an electron transport layer, an electron injection layer, and one or more of layers which simultaneously perform electron transport and electron injection, and one or more of the layers include the indole compound according to the present invention.
It is preferable that the organic material layer includes one or more of a hole injection layer, a hole transport layer, and a layer which simultaneously performs hole injection and hole transport, and one or more of the layers include the indole compound according to the present invention.
It is preferable that the organic material layer includes a hole transport layer, an electron blocking layer, and one or more of the hole transport and electron blocking layers, and one or more of the layers include the indole compound according to the present invention.
The organic material layer may have a multi-layer structure including, but not limited to, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, etc., and may have a single-layer structure.
As the anode material, a material having a large work function is generally preferred so that holes are smoothly injected into the organic material layer. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc or gold, or alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); combinations of metals and oxides, e.g. ZnO: Al or SnO2Sb; conducting polymers, e.g. poly (3-methyl compounds), poly [3,4- (ethylene-1, 2-dioxy) compounds](PEDOT), polypyrrole, and polyaniline, but are not limited thereto.
As the cathode material, a material having a small work function is generally preferred so that electrons are smoothly injected into the organic material layer. Specific examples of cathode materials that can be used in the present invention include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead, or alloys thereof; materials of multilayer construction, e.g. LiF/Al or LiO2Al, etc., but are not limited thereto.
As the hole injecting material, a material having a Highest Occupied Molecular Orbital (HOMO) between the work function of the anode material and the Highest Occupied Molecular Orbital (HOMO) of the surrounding organic material layer is preferable as a material that facilitates the reception of holes from the anode at a low voltage. Specific examples of the hole injection material include metalloporphyrin, oligothiophene, arylamine-based organic material, hexanenitrile-based hexaazatriphenylene-based organic material, quinacridone-based organic material, perylene-based organic material, anthraquinone, polyaniline-based or polythiophene-based conductive polymer, and the like, but are not limited thereto.
As the hole transport material, a material having high hole mobility is suitable as a material that receives holes from the anode or the hole injection layer and transports the holes to the light emitting layer. Specific examples thereof include, but are not limited to, arylamine-based organic materials, conductive polymers, or block copolymers having both conjugated and non-conjugated portions, and the like.
As the light-emitting material, a material having quantum efficiency favorable to fluorescence or phosphorescence is preferable as a material capable of emitting light in the visible light region by receiving holes and electrons from the hole transport layer and the electron transport layer, respectively, and combining the holes and the electrons. Specific examples thereof include 8-hydroxy-quinoline aluminum complex (Alq)3) A carbazole-based compound, a dimeric styryl compound, BAlq, a 10-hydroxybenzoquinoline-metal compound, a benzothiazole-based, a benzimidazole-based compound, a poly (p-phenylene vinylene) (PPV) -based polymer, a spiro compound, polyfluorene, rubrene, or the like, but is not limited thereto.
The organic light emitting device according to the present invention may be a top emission type, a bottom emission type, or a double-sided emission type, depending on the material used.
The compounds according to the present specification can also be used for organic electronic devices using a principle similar to that of organic light emitting devices, including organic solar cells, organic photoconductors, organic transistors, and the like.
The invention has the beneficial effects that:
the indole compound provided by the invention can be used as a material of an organic material layer of an organic light-emitting device, and particularly, the efficiency, voltage, brightness and service life of the organic light-emitting device prepared by using the indole compound provided by the invention as a main material of a light-emitting layer are greatly improved compared with those of the conventional OLED material, and particularly, the service life attenuation of the device is greatly improved.
The preparation method of the indole compound provided by the invention is simple and easy to implement, high in yield and easy to industrialize.
Detailed Description
< preparation example 1> Synthesis of Compound 1
a) In a 500mL round-bottom flask, under a nitrogen atmosphere, starting material A-1(50mmol) and starting material B (50mmol) were dissolved in 300mL dry toluene. Then, sodium t-butoxide (100mmol) and 2-dicyclohexylphosphonium-2, 4, 6-triisopropylbiphenyl (10mmol) were added to the flask, followed by palladium acetate (2.5 mmol). The reaction was heated to 100 ℃ and stirred for 10 hours. After completion of the reaction, the temperature was lowered to room temperature, the salt and the catalyst were removed, toluene was concentrated, and recrystallization was carried out using 200mL of ethanol to obtain intermediate C-1(16.56g, 41mmol yield: 82%).
b) After completely dissolving intermediate C-1(40mmol) and intermediate D-1(40mmol) in a mixed solution of 150mL of toluene and 50mL of tetrahydrofuran in a 500mL round-bottomed flask, p-toluenesulfonic acid (80mmol) was added thereto, and the resultant was heated to 50 ℃ and stirred for 2 hours. After the temperature was lowered to room temperature, 100mL of distilled water and sodium carbonate were added to the reaction solution to neutralize the solution. The organic phase was concentrated in at least one solvent, and the mixture was added dropwise to a cold ethanol solution to precipitate intermediate E-1(14.4g,36mmol, 90% yield).
c) After intermediate E-1(35mmol) and intermediate F-1(35mmol) were completely dissolved in 200mL of dry toluene in a 500mL round-bottom flask under nitrogen atmosphere, sodium tert-butoxide (70mmol) was added thereto, followed by tri-tert-butylphosphine (7.0mmol) and tris (dibenzylideneacetone) dipalladium (0.35mmol), and the resultant was heated to 100 ℃ and stirred for 12 hours. After the temperature was lowered to room temperature, the resultant was filtered to remove salts, toluene was concentrated, and the resultant was subjected to column chromatography using dichloromethane: petroleum ether ═ 1:5 to prepare compound 1(27.3mmol,13.0g, yield: 78%). ESI-MS (M/z) (M +): theoretical value is 477.21, found 477.25.
< preparation example 2> Synthesis of Compound 7
Compound 7 was prepared according to the synthetic procedure for Compound 1 of preparation 1, except that intermediate F-7 was used in place of intermediate F-1. Compound 7 was obtained (yield: 82%). ESI-MS (M/z) (M +): theoretical value is 577.24, found 577.54.
< preparation example 3> Synthesis of Compound 15
Compound 15 was prepared according to the synthetic procedure for Compound 1 of preparation 1, except that intermediate F-15 was used in place of intermediate F-1. Compound 15 was obtained (yield: 80%). ESI-MS (M/z) (M +): theoretical value is 642.27, found 642.37.
< preparation example 4> Synthesis of Compound 21
Compound 21 was prepared according to the synthetic procedure for Compound 1 of preparation example 1, except that starting material A-21, intermediate F-21, was used in place of A-1, F-1. Compound 21 was obtained (yield: 81%). ESI-MS (M/z) (M +): theoretical value is 567.22, found 567.52.
< preparation example 5> Synthesis of Compound 36
Compound 36 was prepared according to the synthetic procedure for Compound 1 of preparation 1, except that intermediate F-36 was used in place of F-1. Compound 36 was obtained (yield: 84%). ESI-MS (M/z) (M +): theoretical value is 593.27, found 593.15.
< preparation example 6> Synthesis of Compound 44
Compound 44 was prepared according to the synthetic procedure for Compound 1 of preparation example 1, except that starting materials A-44, intermediate F-44 were used in place of A-1, F-1. Compound 44 was obtained (yield: 77%). ESI-MS (M/z) (M +): theoretical value is 554.24, found 554.28.
< preparation example 7> Synthesis of Compound 45
Compound 45 was prepared according to the synthetic procedure for Compound 1 of preparation example 1, except that starting materials A-44, intermediate F-45 were used in place of A-1, F-1. Compound 45 was obtained (yield: 73%). ESI-MS (M/z) (M +): theoretical value is 555.23, found 555.55.
< preparation example 8> Synthesis of Compound 49
Compound 49 was prepared according to the synthetic procedure for Compound 1 of preparation 1, except that intermediate F-49 was used in place of intermediate F-1. Compound 49 was obtained (yield: 80%). ESI-MS (M/z) (M +): theoretical value is 681.28, found 681.71.
< preparation example 9> Synthesis of Compound 51
Compound 51 was prepared according to the synthetic procedure for Compound 1 of preparation 1, except that intermediate F-51 was used in place of intermediate F-1. Compound 51 was obtained (yield: 73%). ESI-MS (M/z) (M +): theoretical value is 708.29, found 708.61.
< preparation example 10> Synthesis of Compound 64
Compound 64 was prepared according to the synthetic procedure for Compound 1 of preparation 1, except that starting material A-64 was used in place of A-1. Compound 64 was obtained (yield: 83%). ESI-MS (M/z) (M +): theoretical value is 552.26, found 552.72.
< preparation example 11> Synthesis of Compound 71
Compound 71 was prepared according to the synthetic procedure for compound 1 of preparation 1, except that starting material a-71 was used instead of a-1. Compound 71 was obtained (yield: 79%). ESI-MS (M/z) (M +): theoretical value is 601.24, found 601.42.
< preparation example 11> Synthesis of Compound 76
Compound 76 was prepared according to the synthetic procedure for Compound 1 of preparation 1, except that intermediate D-76 was used in place of intermediate D-1. Compound 76 was obtained (yield: 85%). ESI-MS (M/z) (M +): theoretical value is 353.18, found 353.48.
Device preparation example 1: an organic light-emitting device, the preparation steps of which comprise:
a) cleaning the ITO anode layer on the transparent substrate layer, respectively ultrasonically cleaning the ITO anode layer with deionized water, acetone and ethanol for 15 minutes, and then treating the ITO anode layer in a plasma cleaner for 2 minutes; b) evaporating a hole injection layer material HAT-CN on the ITO anode layer in a vacuum evaporation mode, wherein the thickness of the hole injection layer material HAT-CN is 10nm, and the hole injection layer material HAT-CN is used as a hole injection layer; c) evaporating a hole transport material NPB on the hole injection layer in a vacuum evaporation mode, wherein the thickness of the hole transport material NPB is 60nm, and the hole transport layer is a hole transport layer; d) a light-emitting layer was deposited on the hole-transporting layer by evaporation, using the compound 1 of example 1 as a host material, Ir (ppy)3As doping material, Ir (ppy)3The mass ratio of the compound to the compound 1 is 10:90, and the thickness is 30 nm; f) evaporating an electron transport material TPBI on the light-emitting layer in a vacuum evaporation mode, wherein the thickness is 40 nm; g) vacuum evaporating an electron injection layer LiF on the electron transport layer, wherein the thickness of the electron injection layer LiF is 1nm, and the electron injection layer is the electron injection layer; h) vacuum evaporating cathode Al (100nm) on the electron injection layer, wherein the cathode is a cathode reflection electrode layer;
device example 2: this embodiment differs from device embodiment 1 in that: the host material of the light-emitting layer of the organic light-emitting device is the compound 7 of the present invention.
Device example 3: this embodiment differs from device embodiment 1 in that: the host material of the light-emitting layer of the organic light-emitting device is the compound 15 of the present invention.
Device example 4: this embodiment differs from device embodiment 1 in that: the host material of the light-emitting layer of the organic light-emitting device is the compound 21 of the present invention.
Device example 5: this embodiment differs from device embodiment 1 in that: the host material of the light-emitting layer of the organic light-emitting device is the compound 36 of the present invention.
Device example 6: this embodiment differs from device embodiment 1 in that: the host material of the light-emitting layer of the organic light-emitting device is the compound 44 of the present invention.
Device example 7: this embodiment differs from device embodiment 1 in that: the host material of the light-emitting layer of the organic light-emitting device is the compound 45 of the present invention.
Device example 8: this embodiment differs from device embodiment 1 in that: the host material of the light-emitting layer of the organic light-emitting device is the compound 49 of the present invention.
Device example 9: this embodiment differs from device embodiment 1 in that: the host material of the light-emitting layer of the organic light-emitting device is the compound 51 of the present invention.
Device example 10: this example is different from device example 1 in that the host material of the light-emitting layer of the organic light-emitting device is the compound 64 of the present invention.
Device example 11: this example is different from device example 1 in that the host material of the light-emitting layer of the organic light-emitting device is the compound 71 of the present invention.
Device example 12: this example is different from device example 1 in that the host material of the light-emitting layer of the organic light-emitting device is the compound 76 of the present invention.
Device comparative example 1: this example is different from device example 1 in that the host material of the light-emitting layer of the organic light-emitting device is CBP.
Electroluminescent properties of the manufactured OLED
The voltage, current density, luminance, and lifetime of the organic light emitting devices manufactured according to the measurement device examples 1 to 12 and comparative example 1 are shown in the following table.
The results in the table show that the organic compound with the indole compound as the core can be applied to the preparation of an OLED light-emitting device, and compared with the device comparative example 1, the efficiency, the voltage, the brightness and the service life of the organic compound are greatly improved compared with the known OLED material, and particularly the service life attenuation of the device is greatly improved.
It should be understood that the above examples are only for clarity of illustration and are not intended to limit the embodiments. Other variations and modifications will be apparent to persons skilled in the art in light of the above description. And are neither required nor exhaustive of all embodiments. And obvious variations or modifications therefrom are within the scope of the invention.
Claims (10)
1. An indole compound represented by the following formula 1:
wherein,
ar is a substituted or unsubstituted aryl, substituted or unsubstituted arylamine, or substituted or unsubstituted heterocyclic group;
l is a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroaryl;
m is an integer of 0-2; n is an integer of 0 or more;
R1to R7The same or different from each other, and each independently is hydrogen, deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted alkylsulfonyl group, a substituted or unsubstituted arylsulfonyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aralkenyl group, a substituted or unsubstituted alkylaryl group, a substituted or unsubstituted aralkylamino group, a substituted or unsubstituted heteroarylamino group, a substituted or unsubstituted arylamino group, A substituted or unsubstituted aryl phosphine group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group;
x is-O-, -S-, -SO2-、-C(R10)(R11)-、-N(R12)-、-Si(R13)(R14)-、-Sn(R15)(R16) -or-Ge (R)17)(R18)-；
R8～R18Is substituted or unsubstituted C1-C60 alkyl, C3-C60 cycloalkyl, substituted or unsubstituted C2-C60 alkenyl, C3-C60 cycloalkenyl, substituted or unsubstituted C3-C60 alkynyl or C3-C60 cycloalkynyl; substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 aralkylamino, substituted or unsubstituted C6-C60 heteroarylamino, substituted or unsubstituted C6-C60 arylamino, or C6-C60 heteroaryl.
2. The indole compound according to claim 1, which is any one of structures represented by chemical formulas 2 to 6:
3. the indole compound of claim 1, wherein Ar is a substituted or unsubstituted polycyclic aryl group of 6 to 40 carbon atoms, an arylamine group of 6 to 40 carbon atoms, or a substituted or unsubstituted heterocyclic group of 2 to 40 carbon atoms.
4. The indole compound of claim 1, wherein- (L) n-Ar is any one of the structures selected from:
5. the indole compound of claim 1, selected from any of the following structures:
6. a process for preparing the indole compound of claim 1, comprising the steps of:
step 1, preparation of intermediate C
Dissolving a raw material A and a raw material B in toluene under the nitrogen atmosphere, adding sodium tert-butoxide and 2-dicyclohexyl phosphorus-2, 4, 6-triisopropyl biphenyl, adding palladium acetate, heating the reaction, stirring the reaction, cooling to room temperature after the reaction is finished, removing salt and a catalyst, concentrating the toluene, and recrystallizing by using ethanol to obtain an intermediate C;
step 2, preparation of intermediate E
Dissolving the intermediate C and the intermediate D in a mixed solution of toluene and tetrahydrofuran, adding p-toluenesulfonic acid into the mixed solution, heating the obtained product, stirring for reaction, reducing the temperature to room temperature, adding distilled water and sodium carbonate into a reaction solution to neutralize the solution to be neutral, separating, extracting, concentrating an organic phase by using at least one solvent, dropwise adding the organic phase into cold ethanol, and separating out to obtain an intermediate E;
step 3, preparation of compound of chemical formula 1
After dissolving the intermediate E and the intermediate F in toluene under a nitrogen atmosphere, adding sodium tert-butoxide thereto, then adding tri-tert-butylphosphine and tris (dibenzylideneacetone) dipalladium, heating the resultant to perform a stirring reaction, after lowering the temperature to room temperature, filtering the resultant to remove salts, concentrating toluene, and passing the resultant through a column using dichloromethane and petroleum ether to prepare a compound 1;
the synthetic route is as follows:
wherein Y is halogen.
7. An organic light emitting device comprising: a first electrode, a second electrode, and one or more layers of organic material disposed between the first electrode and the second electrode, wherein one or more of the layers of organic material comprises the indole compound of any one of claims 1-5 or the indole compound prepared according to claim 6.
8. The organic light-emitting device according to claim 7, wherein the organic material layer comprises a light-emitting layer, and the light-emitting layer comprises the indole compound according to any one of claims 1 to 5 or the indole compound produced according to claim 6 as a host of the light-emitting layer.
9. An organic light-emitting device according to claim 8, further comprising another organic compound, metal or metal compound as a dopant.
10. The organic light-emitting device according to claim 7,
wherein the organic material layer comprises an electron transport layer, an electron injection layer, and one or more of a layer in which electron transport and electron injection are simultaneously performed, and one or more of the layers comprises the indole compound according to any one of claims 1 to 5 or the indole compound prepared according to claim 6;
or wherein the organic material layer comprises one or more of a hole injection layer, a hole transport layer, and a layer that simultaneously performs hole injection and hole transport, and one or more of the layers comprises the indole compound of any one of claims 1-5 or the indole compound prepared according to claim 6;
or wherein the organic material layer comprises one or more of a hole transport layer, an electron blocking layer, and a hole transport and electron blocking layer, and one or more of the layers comprises the indole compound of any one of claims 1-5 or the indole compound prepared according to claim 6.
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20130115161A (en) * | 2012-04-10 | 2013-10-21 | 에스에프씨 주식회사 | Heterocyclic com pounds and organic light-emitting diode including the same |
| KR20140103395A (en) * | 2013-02-15 | 2014-08-27 | 에스에프씨 주식회사 | Deuterated organic compounds for organic light-emitting diode and organic light-emitting diode including the same |
| KR20140105634A (en) * | 2013-02-22 | 2014-09-02 | 에스에프씨 주식회사 | Novel organic compounds for organic light-emitting diode and organic light-emitting diode including the same |
| KR20140111214A (en) * | 2013-03-08 | 2014-09-18 | 에스에프씨 주식회사 | An electroluminescent compound and an electroluminescent device comprising the same |
| CN107667102A (en) * | 2015-03-27 | 2018-02-06 | 檀国大学校产学协力团 | Ortho position substitutes hot activation delayed fluorescence material and includes this organic illuminating element |
-
2019
- 2019-04-22 CN CN201910323368.4A patent/CN109942588A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20130115161A (en) * | 2012-04-10 | 2013-10-21 | 에스에프씨 주식회사 | Heterocyclic com pounds and organic light-emitting diode including the same |
| KR20140103395A (en) * | 2013-02-15 | 2014-08-27 | 에스에프씨 주식회사 | Deuterated organic compounds for organic light-emitting diode and organic light-emitting diode including the same |
| KR20140105634A (en) * | 2013-02-22 | 2014-09-02 | 에스에프씨 주식회사 | Novel organic compounds for organic light-emitting diode and organic light-emitting diode including the same |
| KR20140111214A (en) * | 2013-03-08 | 2014-09-18 | 에스에프씨 주식회사 | An electroluminescent compound and an electroluminescent device comprising the same |
| CN107667102A (en) * | 2015-03-27 | 2018-02-06 | 檀国大学校产学协力团 | Ortho position substitutes hot activation delayed fluorescence material and includes this organic illuminating element |
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