WO2022025516A1 - 헤테로고리 화합물, 및 이를 포함하는 유기 발광 소자 - Google Patents
헤테로고리 화합물, 및 이를 포함하는 유기 발광 소자 Download PDFInfo
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- WO2022025516A1 WO2022025516A1 PCT/KR2021/009386 KR2021009386W WO2022025516A1 WO 2022025516 A1 WO2022025516 A1 WO 2022025516A1 KR 2021009386 W KR2021009386 W KR 2021009386W WO 2022025516 A1 WO2022025516 A1 WO 2022025516A1
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- 150000002391 heterocyclic compounds Chemical class 0.000 title claims abstract description 51
- 239000011368 organic material Substances 0.000 claims abstract description 24
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 158
- 229910052805 deuterium Inorganic materials 0.000 claims description 143
- 150000001875 compounds Chemical class 0.000 claims description 75
- 125000004432 carbon atom Chemical group C* 0.000 claims description 62
- 239000000463 material Substances 0.000 claims description 54
- 125000003118 aryl group Chemical group 0.000 claims description 39
- 229910052739 hydrogen Inorganic materials 0.000 claims description 36
- 239000001257 hydrogen Substances 0.000 claims description 36
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 28
- 125000001072 heteroaryl group Chemical group 0.000 claims description 24
- 238000002347 injection Methods 0.000 claims description 19
- 239000007924 injection Substances 0.000 claims description 19
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 230000005525 hole transport Effects 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 230000000903 blocking effect Effects 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- UFHFLCQGNIYNRP-VVKOMZTBSA-N Dideuterium Chemical compound [2H][2H] UFHFLCQGNIYNRP-VVKOMZTBSA-N 0.000 claims 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- 239000010410 layer Substances 0.000 description 72
- -1 polycyclic arylamine Chemical class 0.000 description 67
- 125000001424 substituent group Chemical group 0.000 description 41
- 238000002360 preparation method Methods 0.000 description 30
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 28
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- 238000006243 chemical reaction Methods 0.000 description 24
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 14
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 12
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 12
- 239000000126 substance Substances 0.000 description 11
- 238000006467 substitution reaction Methods 0.000 description 11
- PUMOFXXLEABBTC-UHFFFAOYSA-N 3-(9h-carbazol-3-yl)-9h-carbazole Chemical compound C1=CC=C2C3=CC(C4=CC=C5NC=6C(C5=C4)=CC=CC=6)=CC=C3NC2=C1 PUMOFXXLEABBTC-UHFFFAOYSA-N 0.000 description 10
- 125000002950 monocyclic group Chemical group 0.000 description 10
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 8
- 229910052760 oxygen Inorganic materials 0.000 description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
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- 229940126062 Compound A Drugs 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-MZWXYZOWSA-N benzene-d6 Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
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- 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 6
- 239000002904 solvent Substances 0.000 description 6
- 125000003003 spiro group Chemical group 0.000 description 6
- 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 5
- PKJBWOWQJHHAHG-UHFFFAOYSA-N 1-bromo-4-phenylbenzene Chemical group C1=CC(Br)=CC=C1C1=CC=CC=C1 PKJBWOWQJHHAHG-UHFFFAOYSA-N 0.000 description 5
- WGCOQYDRMPFAMN-ZDUSSCGKSA-N [(3S)-3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxypiperidin-1-yl]-pyrimidin-5-ylmethanone Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)O[C@@H]1CN(CCC1)C(=O)C=1C=NC=NC=1 WGCOQYDRMPFAMN-ZDUSSCGKSA-N 0.000 description 5
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 5
- 239000002019 doping agent Substances 0.000 description 5
- 230000005283 ground state Effects 0.000 description 5
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 5
- 229920000767 polyaniline Polymers 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- SSJXIUAHEKJCMH-PHDIDXHHSA-N (1r,2r)-cyclohexane-1,2-diamine Chemical compound N[C@@H]1CCCC[C@H]1N SSJXIUAHEKJCMH-PHDIDXHHSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- ISXSUKUXUPLGTD-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-[(5-oxopyrrolidin-2-yl)methyl]benzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NCC2NC(CC2)=O)C=CC=1 ISXSUKUXUPLGTD-UHFFFAOYSA-N 0.000 description 4
- MZSAMHOCTRNOIZ-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-phenylaniline Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(NC2=CC=CC=C2)C=CC=1 MZSAMHOCTRNOIZ-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- JOSCNYCOYXTLTN-GFCCVEGCSA-N [3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxyphenyl]-[(3R)-3-(hydroxymethyl)pyrrolidin-1-yl]methanone Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C=CC=1)C(=O)N1C[C@@H](CC1)CO JOSCNYCOYXTLTN-GFCCVEGCSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 238000004770 highest occupied molecular orbital Methods 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 3
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 3
- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 3
- 239000010405 anode material Substances 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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- 238000000576 coating method Methods 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 3
- 238000010494 dissociation reaction Methods 0.000 description 3
- 230000005593 dissociations Effects 0.000 description 3
- 238000005401 electroluminescence Methods 0.000 description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
- 230000009878 intermolecular interaction Effects 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- 150000005839 radical cations Chemical class 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 125000006736 (C6-C20) aryl group Chemical group 0.000 description 2
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 2
- 125000005916 2-methylpentyl group Chemical group 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
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- 150000001412 amines Chemical class 0.000 description 2
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- 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
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- 150000001975 deuterium Chemical group 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000434 field desorption mass spectrometry Methods 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000005241 heteroarylamino group Chemical group 0.000 description 2
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- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
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- 239000000243 solution Substances 0.000 description 2
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- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
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- 238000005051 zero-point vibrational energy Methods 0.000 description 2
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- 125000006743 (C1-C60) alkyl group Chemical group 0.000 description 1
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 1
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- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006023 1-pentenyl group Chemical group 0.000 description 1
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- VFBJMPNFKOMEEW-UHFFFAOYSA-N 2,3-diphenylbut-2-enedinitrile Chemical group C=1C=CC=CC=1C(C#N)=C(C#N)C1=CC=CC=C1 VFBJMPNFKOMEEW-UHFFFAOYSA-N 0.000 description 1
- DSQMLISBVUTWJB-UHFFFAOYSA-N 2,6-diphenylaniline Chemical group NC1=C(C=2C=CC=CC=2)C=CC=C1C1=CC=CC=C1 DSQMLISBVUTWJB-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- WONYVCKUEUULQN-UHFFFAOYSA-N 2-methyl-n-(2-methylphenyl)aniline Chemical group CC1=CC=CC=C1NC1=CC=CC=C1C WONYVCKUEUULQN-UHFFFAOYSA-N 0.000 description 1
- JTMODJXOTWYBOZ-UHFFFAOYSA-N 2-methyl-n-phenylaniline Chemical group CC1=CC=CC=C1NC1=CC=CC=C1 JTMODJXOTWYBOZ-UHFFFAOYSA-N 0.000 description 1
- 125000006024 2-pentenyl group Chemical group 0.000 description 1
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- PWZMFRJQQYRBTQ-UHFFFAOYSA-N 3-(9h-carbazol-3-yl)-9-(4-phenylphenyl)carbazole Chemical compound C1=CC=CC=C1C1=CC=C(N2C3=CC=C(C=C3C3=CC=CC=C32)C=2C=C3C4=CC=CC=C4NC3=CC=2)C=C1 PWZMFRJQQYRBTQ-UHFFFAOYSA-N 0.000 description 1
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- YOZHUJDVYMRYDM-UHFFFAOYSA-N 4-(4-anilinophenyl)-3-naphthalen-1-yl-n-phenylaniline Chemical compound C=1C=C(C=2C(=CC(NC=3C=CC=CC=3)=CC=2)C=2C3=CC=CC=C3C=CC=2)C=CC=1NC1=CC=CC=C1 YOZHUJDVYMRYDM-UHFFFAOYSA-N 0.000 description 1
- DDTHMESPCBONDT-UHFFFAOYSA-N 4-(4-oxocyclohexa-2,5-dien-1-ylidene)cyclohexa-2,5-dien-1-one Chemical class C1=CC(=O)C=CC1=C1C=CC(=O)C=C1 DDTHMESPCBONDT-UHFFFAOYSA-N 0.000 description 1
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- 125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 description 1
- KDOQMLIRFUVJNT-UHFFFAOYSA-N 4-n-naphthalen-2-yl-1-n,1-n-bis[4-(n-naphthalen-2-ylanilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C=C2C=CC=CC2=CC=1)C1=CC=C(N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C3C=CC=CC3=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C3C=CC=CC3=CC=2)C=C1 KDOQMLIRFUVJNT-UHFFFAOYSA-N 0.000 description 1
- ZSMRRZONCYIFNB-UHFFFAOYSA-N 6,11-dihydro-5h-benzo[b][1]benzazepine Chemical group C1CC2=CC=CC=C2NC2=CC=CC=C12 ZSMRRZONCYIFNB-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- QXDWMAODKPOTKK-UHFFFAOYSA-N 9-methylanthracen-1-amine Chemical group C1=CC(N)=C2C(C)=C(C=CC=C3)C3=CC2=C1 QXDWMAODKPOTKK-UHFFFAOYSA-N 0.000 description 1
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- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 125000006617 triphenylamine 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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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
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Definitions
- the present specification relates to a heterocyclic compound, an organic light emitting device including the same, and a composition for an organic material layer of the organic light emitting device.
- the electroluminescent device is a type of self-luminous display device, and has advantages of a wide viewing angle, excellent contrast, and fast response speed.
- the organic light emitting device has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to the organic light emitting device having such a structure, electrons and holes injected from the two electrodes combine in the organic thin film to form a pair, and then disappear and emit light.
- the organic thin film may be composed of a single layer or multiple layers, if necessary.
- the material of the organic thin film may have a light emitting function if necessary.
- a compound capable of forming the light emitting layer by itself may be used, or a compound capable of serving as a host or dopant of the host-dopant light emitting layer may be used.
- a compound capable of performing the roles of hole injection, hole transport, electron blocking, hole blocking, electron transport, electron injection, and the like may be used.
- An object of the present invention is to provide a heterocyclic compound and an organic light emitting device including the same.
- An exemplary embodiment of the present application provides a heterocyclic compound represented by the following formula (1).
- Rc and Rd are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; cyano group; a substituted or unsubstituted C 1 to C 60 alkyl group; a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms; a substituted or unsubstituted C 2 to C 60 alkoxy group; a substituted or unsubstituted C 3 to C 60 cycloalkyl group; a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; a substituted or unsubstituted C 2 to C 60 heteroaryl group; a substituted or unsubstituted phosphine oxide group; and a substituted or unsubstituted amine
- R32 and R33 are the same as or different from each other, and are each independently a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C 2 to C 60 heteroaryl group,
- the content of deuterium in the heterocyclic compound represented by Formula 1 is greater than 0% and less than or equal to 100%.
- another exemplary embodiment of the present application includes a first electrode, a second electrode, and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers is represented by Formula 1 It provides an organic light emitting device comprising a heterocyclic compound to be.
- the heterocyclic compound according to an exemplary embodiment of the present application may be used as an organic material layer material of an organic light emitting device.
- the heterocyclic compound may be used as a material for a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, a charge generation layer, etc. in an organic light emitting device.
- the heterocyclic compound represented by Formula 1 may be used as a material of the light emitting layer of the organic light emitting device.
- 1 to 3 are views schematically showing a stacked structure of an organic light emitting device according to an exemplary embodiment of the present application, respectively.
- An exemplary embodiment of the present application provides a heterocyclic compound represented by the following formula (1).
- Rc and Rd are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; cyano group; a substituted or unsubstituted C 1 to C 60 alkyl group; a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms; a substituted or unsubstituted C 2 to C 60 alkoxy group; a substituted or unsubstituted C 3 to C 60 cycloalkyl group; a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; a substituted or unsubstituted phosphine oxide group; and a substituted or unsubstitute
- R32 and R33 are the same as or different from each other, and are each independently a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C 2 to C 60 heteroaryl group,
- the content of deuterium in the heterocyclic compound represented by Formula 1 is greater than 0% and less than or equal to 100%.
- the HOMO (Highest Occupied Molecular Orbital) level of the compound represented by Formula 1 is widely delocalized in two carbazoles. This can improve the lifespan of the organic light-emitting device by increasing the HOMO level, hole mobility, and stability compared to basic carbazole.
- a compound substituted with deuterium which has a structure that necessarily contains deuterium, and whose atomic mass is twice that of hydrogen, has lower zero point energy and vibrational energy than a compound bonded to hydrogen, so the ground state energy is lowered and intermolecular interaction is reduced. As it becomes weak, the thin film can be made into an amorphous state, thereby improving the lifetime of the device.
- the deuterium-substituted compound has a low ground state energy, stability is improved, and since the dissociation energy of C-D is higher than the dissociation energy of C-H, the stability of the molecule is improved, and the lifespan of a device using such a compound is improved.
- substitution means that a hydrogen atom bonded to a carbon atom of the compound is changed to another substituent, and the position to be substituted is not limited as long as the position at which the hydrogen atom is substituted, that is, the position where the substituent is substitutable, When two or more substituents are substituted, two or more substituents may be the same as or different from each other.
- "when a substituent is not indicated in the chemical formula or compound structure” may mean that all positions that may come as a substituent are hydrogen or deuterium. That is, in the case of deuterium, deuterium is an isotope of hydrogen, and some hydrogen atoms may be isotope deuterium, and the content of deuterium may be 0% to 100%.
- the content of deuterium is 0%, the content of hydrogen is 100%, and all of the substituents explicitly exclude deuterium such as hydrogen If not, hydrogen and deuterium may be mixed and used in the compound.
- deuterium is one of the isotopes of hydrogen, and as an element having a deuteron consisting of one proton and one neutron as an atomic nucleus, hydrogen- It can be expressed as 2, and the element symbol can also be written as D or 2H.
- isotopes have the same atomic number (Z), but isotopes that have different mass numbers (A) have the same number of protons, but neutrons It can also be interpreted as an element with a different number of (neutron).
- 20% of the content of deuterium in the phenyl group represented by means that the total number of substituents that the phenyl group can have is 5 (T1 in the formula), and among them, if the number of deuterium is 1 (T2 in the formula), it will be expressed as 20% can That is, it can be represented by the following structural formula that the content of deuterium in the phenyl group is 20%.
- a phenyl group having a deuterium content of 0% it may mean a phenyl group that does not contain a deuterium atom, that is, has 5 hydrogen atoms.
- the halogen may be fluorine, chlorine, bromine or iodine.
- the alkyl group includes a straight or branched chain having 1 to 60 carbon atoms, and may be further substituted by other substituents.
- the number of carbon atoms in the alkyl group may be 1 to 60, specifically 1 to 40, more specifically, 1 to 20.
- Specific examples include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methyl-butyl group, 1- Ethyl-butyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl- 2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group, cyclohexylmethyl group, octyl group, n-octyl group,
- the alkenyl group includes a straight or branched chain having 2 to 60 carbon atoms, and may be further substituted by other substituents.
- the carbon number of the alkenyl group may be 2 to 60, specifically 2 to 40, more specifically, 2 to 20.
- Specific examples include a vinyl group, 1-propenyl group, isopropenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 3-methyl-1 -Butenyl group, 1,3-butadienyl group, allyl group, 1-phenylvinyl-1-yl group, 2-phenylvinyl-1-yl group, 2,2-diphenylvinyl-1-yl group, 2-phenyl-2 -(naphthyl-1-yl)vinyl-1-yl group, 2,2-bis(diphenyl-1-yl)vinyl-1-yl group, stilbenyl group, styrenyl group, etc., but are not limited thereto.
- the alkynyl group includes a straight or branched chain having 2 to 60 carbon atoms, and may be further substituted by other substituents.
- the carbon number of the alkynyl group may be 2 to 60, specifically 2 to 40, more specifically, 2 to 20.
- the alkoxy group may be a straight chain, branched chain or cyclic chain. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C20. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n -hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc. may be It is not limited.
- the cycloalkyl group includes a monocyclic or polycyclic ring having 3 to 60 carbon atoms, and may be further substituted by other substituents.
- polycyclic means a group in which a cycloalkyl group is directly connected to another ring group or condensed.
- the other ring group may be a cycloalkyl group, but may be a different type of ring group, for example, a heterocycloalkyl group, an aryl group, a heteroaryl group, or the like.
- the carbon number of the cycloalkyl group may be 3 to 60, specifically 3 to 40, more specifically 5 to 20.
- the heterocycloalkyl group includes O, S, Se, N, or Si as a hetero atom, includes a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be further substituted by other substituents.
- polycyclic refers to a group in which a heterocycloalkyl group is directly connected or condensed with another ring group.
- the other ring group may be a heterocycloalkyl group, but may be a different type of ring group, for example, a cycloalkyl group, an aryl group, a heteroaryl group, or the like.
- the heterocycloalkyl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 3 to 20 carbon atoms.
- the aryl group includes a monocyclic or polycyclic ring having 6 to 60 carbon atoms, and may be further substituted by other substituents.
- polycyclic means a group in which an aryl group is directly connected or condensed with another ring group.
- the other ring group may be an aryl group, but may be another type of ring group, such as a cycloalkyl group, a heterocycloalkyl group, a heteroaryl group, and the like.
- the aryl group includes a spiro group.
- the carbon number of the aryl group may be 6 to 60, specifically 6 to 40, more specifically 6 to 25.
- aryl group examples include a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group, a chrysenyl group, a phenanthrenyl group, a perylenyl group, a fluoranthenyl group, a triphenylenyl group, a phenalenyl group, a pyrethyl group Nyl group, tetracenyl group, pentacenyl group, fluorenyl group, indenyl group, acenaphthylenyl group, benzofluorenyl group, spirobifluorenyl group, 2,3-dihydro-1H-indenyl group, condensed ring groups thereof and the like, but is not limited thereto.
- the phosphine oxide group specifically includes, but is not limited to, a diphenylphosphine oxide group, a dinaphthylphosphine oxide, and the like.
- the silyl group is a substituent including Si and the Si atom is directly connected as a radical, and is represented by -SiR104R105R106, R104 to R106 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; an alkyl group; alkenyl group; alkoxy group; cycloalkyl group; aryl group; And it may be a substituent consisting of at least one of a heterocyclic group.
- silyl group examples include a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like. It is not limited.
- the fluorenyl group may be substituted, and adjacent substituents may combine with each other to form a ring.
- the spiro group is a group including a spiro structure, and may have 15 to 60 carbon atoms.
- the spiro group may include a structure in which a 2,3-dihydro-1H-indene group or a cyclohexane group is spiro bonded to a fluorenyl group.
- the spiro group may include any one of the groups of the following structural formula.
- the heteroaryl group includes S, O, Se, N or Si as a hetero atom, and includes a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be further substituted by other substituents.
- the polycyclic refers to a group in which a heteroaryl group is directly connected or condensed with another ring group.
- the other ring group may be a heteroaryl group, but may be a different type of ring group, for example, a cycloalkyl group, a heterocycloalkyl group, an aryl group, or the like.
- the heteroaryl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 3 to 25 carbon atoms.
- heteroaryl group examples include a pyridyl group, a pyrrolyl group, a pyrimidyl group, a pyridazinyl group, a furanyl group, a thiophene group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group group, isothiazolyl group, triazolyl group, furazanyl group, oxadiazolyl group, thiadiazolyl group, dithiazolyl group, tetrazolyl group, pyranyl group, thiopyranyl group, diazinyl group, oxazinyl group , thiazinyl group, deoxynyl group, triazinyl group, tetrazinyl group, quinolyl group, isoquinolyl group, quinazolinyl group, isoquinazol
- the amine group is a monoalkylamine group; monoarylamine group; monoheteroarylamine group; -NH 2 ; dialkylamine group; diarylamine group; diheteroarylamine group; an alkylarylamine group; an alkyl heteroarylamine group; And it may be selected from the group consisting of an aryl heteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30.
- the amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, a dibiphenylamine group, an anthracenylamine group, 9- Methyl-anthracenylamine group, diphenylamine group, phenylnaphthylamine group, ditolylamine group, phenyltolylamine group, triphenylamine group, biphenylnaphthylamine group, phenylbiphenylamine group, biphenylfluorene
- the arylene group means that the aryl group has two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the aryl group described above may be applied.
- the heteroarylene group means that the heteroaryl group has two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the heteroaryl group described above may be applied.
- the "adjacent" group means a substituent substituted on an atom directly connected to the atom in which the substituent is substituted, a substituent sterically closest to the substituent, or another substituent substituted on the atom in which the substituent is substituted.
- two substituents substituted at an ortho position in a benzene ring and two substituents substituted at the same carbon in an aliphatic ring may be interpreted as "adjacent" groups.
- the content of deuterium in the heterocyclic compound represented by Formula 1 is greater than 0%, 100% or less.
- the content of deuterium in the heterocyclic compound represented by Formula 1 is 10% or more and 100% or less.
- the content of deuterium in the heterocyclic compound represented by Formula 1 is 20% or more and 100% or less.
- the content of deuterium in the heterocyclic compound represented by Formula 1 is 40% or more and 100% or less.
- the content of deuterium based on the positions at which Rc and Rd may be substituted may be 0% or more and 100% or less, and deuterium based on the positions where Rc and Rd may be substituted
- the content of is 0%
- the content of deuterium in at least one of R32 and R33 is greater than 0% and less than or equal to 100%.
- the content of deuterium is greater than 0% and less than or equal to 100% based on the position at which Rc and Rd may be substituted, and the content of deuterium in at least one of R32 and R33 is 0% or more , may be 100% or less.
- the content of deuterium is greater than 0% and 100% or less based on the position at which Rc and Rd may be substituted, and the content of deuterium in both R32 and R33 may be 0%. .
- the content of deuterium is greater than 0% and less than or equal to 100% based on the position at which Rc and Rd may be substituted, and the content of deuterium in at least one of R32 and R33 is greater than 0% , may be 100% or less.
- the content of deuterium is greater than 0%, 100% or less, based on the position at which Rc and Rd may be substituted, and the content of deuterium in both R32 and R33 is greater than 0%, 100 % or less.
- the content of deuterium is 0% or more and 100% or less based on the position at which Rc may be substituted, and the content of deuterium based on the position where Rd may be substituted is 0% or more and 100% % or less, and when the content of deuterium is 0% based on the position where Rc and Rd may be substituted, the content of deuterium in at least one of R32 and R33 is greater than 0% and less than or equal to 100%.
- the content of deuterium is 0% or more and 100% or less based on the position at which Rc may be substituted, and the content of deuterium based on the position where Rd may be substituted is 0% or more and 100% % or less, when the sum of the contents of substituted deuterium based on the positions where Rc and Rd may be substituted is greater than 0%.
- R32 and R33 each independently have a deuterium content of 0% or more and 100% or less.
- R32 and R33 may each independently have a deuterium content of 0% or more and 100% or less, and when both R32 and R33 have a deuterium content of 0%, Rc and Rd are substituted Based on the possible positions, the content of deuterium is greater than 0% and less than or equal to 100%.
- R32 and R33 may each independently have a deuterium content of 0% or more and 100% or less, and at least one of R32 and R33 may have a deuterium content of more than 0%.
- R32 and R33 each independently have a deuterium content of 0% or more and 100% or less, and at least one of R32 and R33 has a deuterium content of more than 0%, and the Rc and Based on the position where Rd may be substituted, the content of deuterium may be 0%.
- R32 and R33 each independently have a deuterium content of 0% or more and 100% or less, and at least one of R32 and R33 has a deuterium content of more than 0%, and the Rc and Based on the position where Rd may be substituted, the content of deuterium may be greater than 0% and less than or equal to 100%.
- heterocyclic compound represented by Formula 1 necessarily contains at least one deuterium.
- Rc and Rd are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Alternatively, it may be a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, and the content of deuterium based on the position at which Rc and Rd may be substituted may be 0% or more and 100% or less.
- Rc and Rd are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Alternatively, it may be a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, and the content of deuterium based on the positions at which Rc and Rd may be substituted may be 0% or more and 100% or less.
- Rc and Rd are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Alternatively, it may be a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and the content of deuterium based on the positions at which Rc and Rd may be substituted may be 0% or more and 100% or less.
- Rc and Rd are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted phenyl group; Alternatively, it may be a substituted or unsubstituted biphenyl group, and the content of deuterium based on a position where Rc and Rd may be substituted may be 0% or more and 100% or less.
- R32 and R33 each independently have a content of deuterium greater than 0% and less than or equal to 100%.
- Rc and Rd are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Alternatively, it may be a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, and the content of deuterium based on the position at which Rc and Rd may be substituted may be greater than 0% or less than 100%.
- Rc and Rd are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Alternatively, it may be a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, and the content of deuterium based on the position at which Rc and Rd may be substituted may be greater than 0%, 100% or less.
- Rc and Rd are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Alternatively, it may be a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and the content of deuterium based on a position where Rc and Rd may be substituted may be greater than 0% and less than or equal to 100%.
- Rc and Rd are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted phenyl group; Alternatively, it may be a substituted or unsubstituted biphenyl group, and the content of deuterium based on the positions at which Rc and Rd may be substituted may be greater than 0%, 100% or less.
- r and s are integers of 2 to 7, when r is 2 or more, Rc is the same as or different from each other, and when s is 2 or more, Rd is the same as or different from each other, and among Rc At least two of them are deuterium, and at least two of Rd are deuterium. Rc and Rd are each substituted by at least two or more.
- Rc and Rd are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or it may be a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, at least two of Rc is deuterium, and at least two of Rd is deuterium.
- Rc and Rd are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or it may be a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, at least two of Rc is deuterium, and at least two of Rd is deuterium.
- Rc and Rd are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or it may be a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, at least two of Rc is deuterium, and at least two of Rd is deuterium.
- Rc and Rd are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted phenyl group; Or it may be a substituted or unsubstituted biphenyl group, at least two of Rc is deuterium, and at least two of Rd is deuterium.
- Rc and Rd are the same as or different from each other, and each independently hydrogen; heavy hydrogen; phenyl group; Or it may be a biphenyl group, at least two of Rc is deuterium, and at least two of Rd is deuterium.
- Rc and Rd are deuterium.
- R32 and R33 are the same as or different from each other, and each independently a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or it may be a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, wherein R32 and R33 each independently have a deuterium content of 0% or more and 100% or less.
- R32 and R33 are the same as or different from each other, and each independently a substituted or unsubstituted silyl group; a substituted or unsubstituted C 6 to C 40 aryl group; Or it may be a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms, wherein R32 and R33 each independently have a deuterium content of 0% or more and 100% or less.
- R32 and R33 are the same as or different from each other, and each independently a substituted or unsubstituted silyl group; a substituted or unsubstituted C6-C20 aryl group; Or it may be a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms, wherein R32 and R33 each independently have a deuterium content of 0% or more and 100% or less.
- R32 and R33 are the same as or different from each other, and each independently a substituted or unsubstituted silyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted triphenyl group; a substituted or naphthyl group; a substituted or unsubstituted dibenzothiophene group; Alternatively, it may be a substituted or unsubstituted dibenzofuran group, wherein R32 and R33 each independently have a deuterium content of 0% or more and 100% or less.
- R32 and R33 each have a deuterium content of 100%, and Rc and Rd each have a deuterium content of 0%.
- each of R32 and R33 has a deuterium content of 0%, and Rc and Rd each have a deuterium content of 100%.
- the content of deuterium in each of R32, R33, Rc and Rd is 100%. That is, the heterocyclic compound represented by Formula 1 has a deuterium content of 100%.
- the content of deuterium in R32 and R33 is 0%.
- Rc and Rd are deuterium, and the content of deuterium in R32 and R33 is 0%.
- R32 and R33 are the same as or different from each other, and each independently a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, and the content of deuterium in R32 and R33 is 0%.
- R32 and R33 are the same as or different from each other, and each independently a substituted or unsubstituted silyl group; a substituted or unsubstituted C 6 to C 40 aryl group; or a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms, and the content of deuterium in R32 and R33 is 0%.
- R32 and R33 are the same as or different from each other, and each independently a substituted or unsubstituted silyl group; a substituted or unsubstituted C6-C20 aryl group; or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms, and the content of deuterium in R32 and R33 is 0%.
- R32 and R33 are the same as or different from each other, and each independently a substituted or unsubstituted silyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted triphenyl group; a substituted or naphthyl group; a substituted or unsubstituted dibenzothiophene group; or a substituted or unsubstituted dibenzofuran group, and the content of deuterium in R32 and R33 is 0%.
- Chemical Formula 1 may be represented by any one of the following compounds, but is not limited thereto.
- the heterocyclic compound according to an exemplary embodiment of the present application is characterized in that it is represented by Formula 1 above. More specifically, the heterocyclic compound represented by Chemical Formula 1 may be used as an organic material layer material of an organic light emitting device due to the structural characteristics of the core structure and substituents as described above.
- the heterocyclic compound has a high glass transition temperature (Tg) and excellent thermal stability. This increase in thermal stability is an important factor in providing driving stability to the device.
- the heterocyclic compound according to an exemplary embodiment of the present application may be prepared by a multi-step chemical reaction. Some intermediate compounds are prepared first, and the compound of Formula 1 can be prepared from the intermediate compounds. More specifically, the heterocyclic compound according to an exemplary embodiment of the present application may be prepared based on Preparation Examples to be described later.
- organic light emitting device including the heterocyclic compound represented by Formula 1 above.
- the "organic light emitting device” may be expressed in terms such as “organic light emitting diode”, “OLED (Organic Light Emitting Diodes)", “OLED device”, “organic electroluminescent device”, and the like.
- the heterocyclic compound may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device.
- the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.
- the organic light emitting device includes a first electrode, a second electrode, and one or more organic material layers provided between the first and second electrodes, and at least one of the organic material layers. includes a heterocyclic compound represented by Formula 1 above.
- the heterocyclic compound represented by Formula 1 is included in the organic material layer, the luminous efficiency and lifespan of the organic light-emitting device are excellent.
- the first electrode may be an anode
- the second electrode may be a cathode
- the first electrode may be a cathode
- the second electrode may be an anode
- the organic light emitting device may be a blue organic light emitting device, and the heterocyclic compound according to Chemical Formula 1 may be used as a material of the blue organic light emitting device.
- the organic light emitting device may be a green organic light emitting device, and the heterocyclic compound according to Chemical Formula 1 may be used as a material of the green organic light emitting device.
- the organic light emitting device may be a white organic light emitting device, and the heterocyclic compound according to Chemical Formula 1 may be used as a material of the white organic light emitting device.
- the organic light emitting device may be a red organic light emitting device, and the heterocyclic compound according to Formula 1 may be used as a material of the red organic light emitting device.
- the organic material layer includes one or more emission layers, and the emission layer includes the heterocyclic compound represented by Formula 1 above.
- the heterocyclic compound represented by Formula 1 is included in the light emitting layer of the organic material layer, the luminous efficiency and lifespan of the organic light emitting device are more excellent.
- the organic material layer may include a light emitting layer, and the light emitting layer may include the heterocyclic compound as a host material of the light emitting material.
- the organic light emitting device of the present invention may further include one or more layers selected from the group consisting of a light emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, a hole auxiliary layer, and a hole blocking layer.
- the organic light emitting device may be manufactured by a conventional method and material for manufacturing an organic light emitting device, except for forming an organic material layer using the above-described heterocyclic compound.
- 1 to 3 illustrate the stacking order of the electrode and the organic material layer of the organic light emitting device according to an exemplary embodiment of the present application.
- the scope of the present application be limited by these drawings, and the structure of an organic light emitting device known in the art may also be applied to the present application.
- an organic light-emitting device in which an anode 200 , an organic material layer 300 , and a cathode 400 are sequentially stacked on a substrate 100 is illustrated.
- an organic light emitting device in which a cathode, an organic material layer, and an anode are sequentially stacked on a substrate may be implemented.
- the organic light emitting diode according to FIG. 3 includes a hole injection layer 301 , a hole transport layer 302 , a light emitting layer 303 , a hole blocking layer 304 , an electron transport layer 305 , and an electron injection layer 306 .
- a hole injection layer 301 a hole transport layer 302 , a light emitting layer 303 , a hole blocking layer 304 , an electron transport layer 305 , and an electron injection layer 306 .
- the scope of the present application is not limited by such a laminated structure, and if necessary, the remaining layers except for the light emitting layer may be omitted, and other necessary functional layers may be further added.
- materials other than the heterocyclic compound of Formula 1 are exemplified below, but these are for illustration only and not for limiting the scope of the present application, may be substituted with known materials.
- anode material Materials having a relatively large work function may be used as the anode material, and transparent conductive oxides, metals, conductive polymers, or the like may be used.
- the anode material include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO 2 : Combination of metals and oxides such as Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDT), polypyrrole, and polyaniline, but are not limited thereto.
- the negative electrode material Materials having a relatively low work function may be used as the negative electrode material, and metal, metal oxide, conductive polymer, or the like may be used.
- the anode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; and a multi-layered material such as LiF/Al or LiO 2 /Al, but is not limited thereto.
- a known hole injection material may be used, for example, a phthalocyanine compound such as copper phthalocyanine disclosed in US Pat. No. 4,356,429 or Advanced Material, 6, p.677 (1994).
- starburst-type amine derivatives such as tris(4-carbazolyl-9-ylphenyl)amine (TCTA), 4,4′,4′′-tri[phenyl(m-tolyl)amino]triphenylamine (m- MTDATA), 1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (m-MTDAPB), polyaniline/Dodecylbenzenesulfonic acid or poly( 3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (Poly(3,4-ethylenedioxythiophene)/Poly(4-styrenesulfonate)), polyaniline/Camphor
- a pyrazoline derivative, an arylamine derivative, a stilbene derivative, a triphenyldiamine derivative, etc. may be used as a hole transport material, and a low molecular weight or high molecular material may be used.
- Examples of the electron transport material include oxadiazole derivatives, anthraquinodimethane and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, tetracyanoanthraquinodimethane and its derivatives, and fluorenone.
- Derivatives, diphenyldicyanoethylene and derivatives thereof, diphenoquinone derivatives, metal complexes of 8-hydroxyquinoline and derivatives thereof, etc. may be used, and polymer materials as well as low molecular weight materials may be used.
- LiF is typically used in the art, but the present application is not limited thereto.
- a red, green, or blue light emitting material may be used as the light emitting material, and if necessary, two or more light emitting materials may be mixed and used.
- a fluorescent material can be used as a light emitting material, it can also be used as a phosphorescent material.
- As the light emitting material a material that emits light by combining holes and electrons respectively injected from the anode and the cathode may be used alone, but materials in which a host material and a dopant material together participate in light emission may be used.
- the organic light emitting device may be a top emission type, a back emission type, or a double side emission type depending on a material used.
- the heterocyclic compound according to an exemplary embodiment of the present application may act on a principle similar to that applied to an organic light emitting device in an organic electronic device including an organic solar cell, an organic photoreceptor, and an organic transistor.
- the target compound can be directly synthesized by adding 2 equivalents of compound A in Preparation Example 1. That is, when Compound A and Compound A' are the same, Preparation Example 1-2 (preparation of Compound 1-2-1) may be omitted.
- the target compound can be directly synthesized by adding 2 equivalents of compound C in Preparation Example 2-2. That is, when compound C and compound C' are the same, Preparation Example 2-3 (preparation of compound 1-26-2) may be omitted.
- compound 1-26-1 was synthesized using condition 7 having the highest substitution rate as a reaction condition.
- substitution rate is calculated as [(the number of deuterium substituted after the chemical reaction)/(the number of hydrogens in the compound before the chemical reaction)]*100.
- Table 8 is the measurement value of 1 H NMR (CDCl 3 , 300Mz)
- Table 9 is the measurement value of the FD-mass spectrometer (FD-MS: Field desorption mass spectrometry).
- a glass substrate coated with indium tin oxide (ITO) to a thickness of 1,500 ⁇ was washed with distilled water ultrasonically. After washing with distilled water, ultrasonic washing was performed with a solvent such as acetone, methanol, isopropyl alcohol, etc., and dried. After transferring the substrate to a plasma cleaner (PT), plasma treatment was performed to remove the ITO work function and residual film in a vacuum state, and then transferred to a thermal deposition equipment for organic deposition.
- ITO indium tin oxide
- a light emitting layer was deposited thereon by thermal vacuum deposition as follows.
- the light emitting layer was deposited by depositing the compound represented by Chemical Formula 1 of the present invention described in Table 10 below to a thickness of 400 ⁇ as a host, and doping a green phosphorescent dopant [Ir(ppy) 3 ] by 7% of the thickness of the light emitting layer deposition was deposited. Thereafter, bathocuproine (BCP) was deposited to a thickness of 60 ⁇ as a hole blocking layer, and Alq 3 was deposited thereon to a thickness of 200 ⁇ as an electron transport layer.
- BCP bathocuproine
- lithium fluoride (LiF) is deposited on the electron transport layer to a thickness of 10 ⁇ to form an electron injection layer, and then an aluminum (Al) cathode is deposited to a thickness of 1,200 ⁇ on the electron injection layer to form a cathode.
- Al aluminum
- T 90 was measured.
- T 90 denotes a lifetime (unit: h, time) that is 90% of the initial luminance.
- Example 1 A 6.11 44.1 Green 59 Comparative Example 2 B 6.15 45.5 62 Comparative Example 3 C 6.23 43.6 68 Comparative Example 4 D 6.48 42.9 60 Comparative Example 5 E 6.90 40.7 50 Example 1 1-2 5.68 55.4 90 Example 2 1-4 5.34 54.8 84 Example 3 1-5 5.48 53.9 88 Example 4 1-7 5.59 56.0 80 Example 5 1-8 5.61 55.8 86 Example 6 1-9 5.79 53.7 88 Example 7 1-26 3.71 74.6 130 Example 8 1-28 3.60 75.0 124 Example 9 1-29 3.88 68.7 128 Example 10 1-31 3.92 69.1 120 Example 11 1-32 3.67 70.5 126 Example 12 1-33 3.83 71.3 128 Example 13 1-50 4.03 70.3 150 Example 14 1-51 4.28 74.7 146 Example 15 1-52 4.16 75.1 142 Example 16 1-53 4.26 79.6 148 Example 17 1-55 4.33 77.5 138
- the organic light emitting device using the organic light emitting layer material of the present application has a lower driving voltage, improved luminous efficiency and significantly improved lifespan compared to Comparative Examples 1 to 5.
- the compound according to the present application is a compound substituted with deuterium
- the compound of Comparative Example is a compound substituted with hydrogen or not biscarbazole.
- the deuterium-substituted compound has a low ground state energy, which improves stability, and increases the dissociation energy of C-D, thereby improving molecular stability and improving lifespan.
- deuterium-substituted compound 1-51 corresponding to the compound according to the present application is hydrogen-substituted Comparative Example Compounds A, B, C, and D. It can be confirmed that the driving and lifespan improvement by the stability and amorphousness of the molecule, and , it was possible to facilitate energy transfer to the dopant and improve the efficiency by minimizing the loss of energy by low vibration energy.
- Comparative Example Compound E unlike biscarbazole, has low HOMO and low hole stability by substituting dibenzofuran at the 3-position of carbazole, so it has lower efficiency, drive, and lifespan than the compound corresponding to the compound according to the present application. I was able to confirm what I had.
- compound 1-29 corresponding to the compound according to the present application substituted with deuterium in biscarbazole can effectively improve the lifespan by effectively stabilizing radical cations
- compound 1-5 substituted with deuterium in an aryl group is bis It does not contribute to the stabilization of radical cations of carbazole.
- the device performance is more improved when the hydrogen of the biscarbazole is substituted with deuterium rather than the hydrogen of the aryl group of the Formula 1 is substituted with deuterium. It was confirmed that excellent (comparison of Compounds 1-5 and 1-29), and that as the substitution rate of deuterium increased, the device performance became more excellent (comparison of Compounds 1-2, 1-26, and 1-50).
- the 3-position of the carbazole refers to the 3-position of the following Chemical Formula A.
- the compound according to the present application has the effect of lowering the driving voltage of the organic light emitting device using the compound as a material of the organic material layer, improving the luminous efficiency, and significantly improving the lifespan due to its structural characteristics.
- the compound according to the present application is used as a material for the light emitting layer, the effect is more excellent.
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Abstract
Description
조건 | 화합물 (g, 당량) |
용매 (g) |
촉매 (mol%) |
온도/시간 (oC, d) |
반응기 | 얻은양, 수율 |
1 | 9H,9'H-3,3'-bicarbazole (1g, 1eq) | D2O(100g) | Pt/C (10 mol%) |
150 oC, 4d | Round flask Under Ar bag |
NO reaction |
2 | 9H,9'H-3,3'-bicarbazole (1g, 1eq) | D2O, i-PrOH, cyclohexane (100g, 50g, 50g) |
Pt/C, Pd/C (10 mol%) | 150 oC, 4d | Round flask Under Ar bag |
NO reaction |
3 | 9H,9'H-3,3'-bicarbazole (1g, 1eq) | D2O, i-PrOH, cyclohexane (100g, 50g, 50g) |
Pt/C, Pd/C (10 mol%) | 200 oC, 2d | sealed tube | NO reaction |
4 | 9H,9'H-3,3'-bicarbazole (1g, 1eq) | D2O, i-PrOH, cyclohexane (100g, 50g, 50g) |
Pt/C, Pd/C (10 mol%) | 150 oC, 4d | sealed tube | NO reaction |
조건 | 화합물 (g, 당량) |
용매 (g, 당량) |
산 (g, 당량) |
온도 | 수율 | 치환율 |
5 | 9H,9'H-3,3'-bicarbazole (1g, 1eq) | 벤젠-D6 (50g, 139.9eq) |
CF3SO3H (17g, 25eq) |
RT | 95% | 46% |
6 | 9H,9'H-3,3'-bicarbazole (1g, 1eq) | 벤젠-D6(50g, 139.9eq) | CF3SO3H (17g, 25eq) |
30oC | 86% | 72% |
7 | 9H,9'H-3,3'-bicarbazole (1g, 1eq) | 벤젠-D6 (50g, 139.9eq) |
CF3SO3H (17g, 25eq) |
40oC | 68% | 95% |
8 | 9H,9'H-3,3'-bicarbazole (1g, 1eq) | DMSO-D6 (50g, 139.9eq) |
CF3SO3H (17g, 25eq) |
40oC | 77% | 53% |
9 | 9H,9'H-3,3'-bicarbazole (1g, 1eq) | DMF-D6 (50g, 139.9eq) |
CF3SO3H (17g, 25eq) |
40oC | 79% | 62% |
조건 | 화합물 (g, 당량) |
용매 (g) |
촉매 (mol%) |
온도/시간 (oC, d) |
반응기 | 얻은양, 수율 |
1 | 1-50-1(1g, 1eq) | D2O (100g) |
Pt/C (10 mol%) |
150 oC, 4d | Round flask Under Ar bag |
NO reaction |
2 | 1-50-1 (1g, 1eq) |
D2O, i-PrOH, cyclohexane (100g, 50g, 50g) |
Pt/C, Pd/C (10 mol%) | 150 oC, 4d | Round flask Under Ar bag |
NO reaction |
3 | 1-50-1 (1g, 1eq) |
D2O, i-PrOH, cyclohexane (100g, 50g, 50g) |
Pt/C, Pd/C (10 mol%) | 200 oC, 2d | sealed tube | NO reaction |
4 | 1-50-1 (1g, 1eq) |
D2O, i-PrOH, cyclohexane (100g, 50g, 50g) |
Pt/C, Pd/C (10 mol%) | 150 oC, 4d | sealed tube | NO reaction |
조건 | 화합물 (g, 당량) |
용매 (g, 당량) |
산 (g, 당량) |
온도 | 수율 | 치환율 |
5 | 1-50-1 (1g, 1eq) |
벤젠-D6 (50g, 139.9eq) |
CF3SO3H (17g, 25eq) |
RT | 93% | 42% |
6 | 1-50-1(1g, 1eq) | 벤젠-D6 (50g, 139.9eq) |
CF3SO3H (17g, 25eq) |
30oC | 83% | 82% |
7 | 1-50-1 (1g, 1eq) |
벤젠-D6 (50g, 139.9eq) |
CF3SO3H (17g, 25eq) |
50oC | 78% | 98% |
8 | 1-50-1 (1g, 1eq) |
DMSO-D6 (50g, 139.9eq) |
CF3SO3H (17g, 25eq) |
50oC | 88% | 59% |
9 | 1-50-1 (1g, 1eq) |
DMF-D6 (50g, 139.9eq) |
CF3SO3H (17g, 25eq) |
50oC | 81% | 60% |
화합물 | 1H NMR(DMSO, 300Mz) |
1-2 | δ = 8.55 (1H, d), 8.30 (1H, d), 8.13~8.19 (2H, m), 7.89~7.99 (4H, m), 7.77 (1H, d), 7.50~7.58 (2H, m), 7.35 (1H, t), 7.16~7.20 (2H, m) |
1-3 | δ = 8.55 (1H, d), 8.30 (1H, d), 8.13~8.19 (2H, m), 7.89~7.99 (4H, m), 7.77 (1H, d), 7.50~7.58 (2H, m), 7.35 (1H, t), 7.16~7.20 (2H, m) |
1-5 | δ = 8.55 (1H, d), 8.30 (1H, d), 8.13~8.19 (2H, m), 7.89~7.99 (4H, m), 7.77 (1H, d), 7.50~7.58 (2H, m), 7.35 (1H, t), 7.16~7.20 (2H, m) |
1-6 | δ = 8.55 (1H, d), 8.30 (1H, d), 8.13~8.19 (2H, m), 7.89~7.99 (4H, m), 7.77 (1H, d), 7.50~7.58 (2H, m), 7.35 (1H, t), 7.16~7.20 (2H, m) |
1-8 | δ = 8.55 (1H, d), 8.30 (1H, d), 8.13~8.19 (2H, m), 7.89~7.99 (4H, m), 7.77 (1H, d), 7.50~7.58 (2H, m), 7.35 (1H, t), 7.16~7.20 (2H, m) |
1-19 | δ = 8.55 (1H, d), 8.30 (1H, d), 8.13~8.19 (2H, m), 7.89~7.99 (4H, m), 7.77 (1H, d), 7.50~7.58 (2H, m), 7.35 (1H, t), 7.16~7.20 (2H, m) |
1-22 | δ = 8.55 (1H, d), 8.30 (1H, d), 8.13~8.19 (2H, m), 7.89~7.99 (4H, m), 7.77 (1H, d), 7.50~7.58 (2H, m), 7.35 (1H, t), 7.16~7.20 (2H, m) |
1-26 | δ = 7.91~7.92 (8H, m), 7.75 (4H, d), 7.41~7.49 (6H, m) |
1-27 | δ = 8.21 (1H, s), 7.41~7.75 (13H, m) |
1-29 | δ = 7.91~7.94 (5H, m), 7.73~7.75 (3H, m), 7.41~7.62 (10H, m) |
1-32 | δ = 8.21 (1H, s), 7.60~7.75 (8H, m), 7.41~7.49 (8H, m) |
1-33 | δ = 8.21 (1H, s), 7.91~7.92 (4H, m), 7.60~7.75 (6H, m), 7.41~7.49 (7H, m) |
1-36 | δ = 8.21 (1H, s), 7.91~7.92 (4H, m), 7.60~7.75 (6H, m), 7.41~7.49 (7H, m), 7.25 (4H, s) |
1-39 | δ = 7.91~7.92 (8H, m), 7.75 (4H, d), 7.41~7.49 (6H, m), 7.25 (4H, s) |
1-44 | δ = 7.91~7.98 (6H, m), 7.75 (2H, d), 7.25~7.54 (8H, m) |
1-50 | δ = 중수소 함량 100%로 1H NMR 피크 없음 |
1-51 | δ = 중수소 함량 100%로 1H NMR 피크 없음 |
1-53 | δ = 중수소 함량 100%로 1H NMR 피크 없음 |
1-54 | δ = 중수소 함량 100%로 1H NMR 피크 없음 |
1-56 | δ = 중수소 함량 100%로 1H NMR 피크 없음 |
1-57 | δ = 중수소 함량 100%로 1H NMR 피크 없음 |
1-58 | δ = 중수소 함량 100%로 1H NMR 피크 없음 |
1-60 | δ = 중수소 함량 100%로 1H NMR 피크 없음 |
1-62 | δ = 중수소 함량 100%로 1H NMR 피크 없음 |
1-63 | δ = 중수소 함량 100%로 1H NMR 피크 없음 |
1-67 | δ = 중수소 함량 100%로 1H NMR 피크 없음 |
1-68 | δ = 중수소 함량 100%로 1H NMR 피크 없음 |
화합물 | FD-Mass | 화합물 | FD-Mass |
1-2 | m/z= 654.91 (C48H14D18N2=654.37) | 1-3 | m/z= 574.79 (C42H14D14N2=574.31) |
1-5 | m/z= 654.91 (C48H14D18N2=654.37) | 1-6 | m/z= 654.91 (C48H14D18N2=654.37) |
1-8 | m/z= 654.91 (C48H14D18N2=654.37) | 1-19 | m/z= 815.15 (C60H14D26N2=814.48) |
1-22 | m/z= 815.15 (C606H14D26N2=814.48) | 1-26 | m/z= 650.88 (C48H18D14N2=650.34) |
1-27 | m/z= 574.79 (C42H14D14N2=574.31) | 1-29 | m/z= 650.88 (C48H18D14N2=650.34) |
1-32 | m/z= 650.88 (C48H18D14N2=650.34) | 1-33 | m/z= 650.88 (C48H18D14N2=650.34) |
1-36 | m/z= 726.98 (C54H22D14N2=726.38) | 1-39 | m/z= 726.98 (C54H22D14N2=726.38) |
1-44 | m/z= 664.87 (C48H16D14N2O=664.32) | 1-50 | m/z= 668.99 (C48D32N2=668.46) |
1-51 | m/z= 588.87 (C42D28N2=588.40) | 1-53 | m/z= 668.99 (C48D32N2=668.46) |
1-54 | m/z= 668.99 (C48D32N2=668.46) | 1-56 | m/z= 668.99 (C48D32N2=668.46) |
1-57 | m/z= 668.99 (C48D32N2=668.46) | 1-58 | m/z= 749.12 (C54D36N2=748.51) |
1-60 | m/z= 749.12 (C54D36N2=748.51) | 1-62 | m/z= 749.12 (C54D36N2=748.51) |
1-63 | m/z= 749.12 (C54D36N2=748.51) | 1-67 | m/z= 829.24 (C60D40N2=828.57) |
1-68 | m/z= 680.96 (C48D30N2O=680.42) |
화합물 | 구동전압 (V) |
효율 (cd/A) |
색좌표 (x, y) |
수명 (T90) |
|
비교예 1 | A | 6.11 | 44.1 | Green | 59 |
비교예 2 | B | 6.15 | 45.5 | 62 | |
비교예 3 | C | 6.23 | 43.6 | 68 | |
비교예 4 | D | 6.48 | 42.9 | 60 | |
비교예 5 | E | 6.90 | 40.7 | 50 | |
실시예 1 | 1-2 | 5.68 | 55.4 | 90 | |
실시예 2 | 1-4 | 5.34 | 54.8 | 84 | |
실시예 3 | 1-5 | 5.48 | 53.9 | 88 | |
실시예 4 | 1-7 | 5.59 | 56.0 | 80 | |
실시예 5 | 1-8 | 5.61 | 55.8 | 86 | |
실시예 6 | 1-9 | 5.79 | 53.7 | 88 | |
실시예 7 | 1-26 | 3.71 | 74.6 | 130 | |
실시예 8 | 1-28 | 3.60 | 75.0 | 124 | |
실시예 9 | 1-29 | 3.88 | 68.7 | 128 | |
실시예 10 | 1-31 | 3.92 | 69.1 | 120 | |
실시예 11 | 1-32 | 3.67 | 70.5 | 126 | |
실시예 12 | 1-33 | 3.83 | 71.3 | 128 | |
실시예 13 | 1-50 | 4.03 | 70.3 | 150 | |
실시예 14 | 1-51 | 4.28 | 74.7 | 146 | |
실시예 15 | 1-52 | 4.16 | 75.1 | 142 | |
실시예 16 | 1-53 | 4.26 | 79.6 | 148 | |
실시예 17 | 1-55 | 4.33 | 77.5 | 138 | |
실시예 18 | 1-56 | 4.22 | 78.6 | 144 | |
실시예 19 | 1-57 | 4.50 | 73.2 | 148 | |
실시예 20 | 1-73 | 4.76 | 74.6 | 82 | |
실시예 21 | 1-74 | 4.71 | 75.0 | 122 | |
실시예 22 | 1-75 | 4.82 | 73.7 | 140 |
Claims (12)
- 하기 화학식 1로 표시되는 헤테로고리 화합물:[화학식 1]상기 화학식 1에서,Rc 및 Rd은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐; 시아노기; 치환 또는 비치환된 탄소수 1 내지 60의 알킬기; 치환 또는 비치환된 탄소수 2 내지 60의 알케닐기; 치환 또는 비치환된 탄소수 2 내지 60의 알키닐기; 치환 또는 비치환된 탄소수 2 내지 60의 알콕시기; 치환 또는 비치환된 탄소수 3 내지 60의 시클로알킬기; 치환 또는 비치환된 탄소수 2 내지 60의 헤테로시클로알킬기; 치환 또는 비치환된 탄소수 6 내지 60의 아릴기; 치환 또는 비치환된 탄소수 2 내지 60의 헤테로아릴기; 치환 또는 비치환된 포스핀옥사이드기; 및 치환 또는 비치환된 아민기로 이루어진 군으로부터 선택되고, r 및 s는 0 내지 7의 정수이고, r이 2 이상인 경우 Rc는 서로 같거나 상이하고, s가 2 이상인 경우 Rd는 서로 같거나 상이하고,R32 및 R33은 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 실릴기; 치환 또는 비치환된 탄소수 6 내지 60의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 60의 헤테로아릴기이고,상기 화학식 1로 표시되는 헤테로고리 화합물의 중수소의 함량은 0% 초과, 100% 이하이다.
- 청구항 1에 있어서, 상기 화학식 1로 표시되는 헤테로고리 화합물의 중수소의 함량은 40% 이상, 100% 이하인 헤테로고리 화합물.
- 청구항 1에 있어서, 상기 Rc 및 Rd가 치환될 수 있는 위치를 기준으로 중수소의 함량은 0% 이상, 100% 이하이고, 상기 Rc 및 Rd가 치환될 수 있는 위치를 기준으로 중수소의 함량이 0%인 경우, 상기 R32 및 R33 중 적어도 하나는 중수소의 함량이 0% 초과, 100% 이하인 헤테로고리 화합물.
- 청구항 1에 있어서, 상기 Rc가 치환될 수 있는 위치를 기준으로 중수소의 함량은 0% 이상 100% 이하이고, Rd가 치환될 수 있는 위치를 기준으로 중수소의 함량은 0% 이상 100% 이하일 수 있으며, 상기 Rc 및 Rd가 치환될 수 있는 위치를 기준으로 각각 중수소의 함량이 0%인 경우, R32 및 R33 중 적어도 하나는 중수소의 함량이 0% 초과, 100% 이하인 헤테로고리 화합물.
- 청구항 1에 있어서, 상기 r 및 s는 2 내지 7의 정수이고, r이 2 이상인 경우 Rc는 서로 같거나 상이하고, s가 2 이상인 경우 Rd는 서로 같거나 상이하며, 상기 Rc중 2개 이상은 중수소이고, 상기 Rd중 2개 이상은 중수소인 것인 헤테로고리 화합물.
- 청구항 5에 있어서, 상기 R32 및 R33의 중수소의 함량은 0%인 헤테로고리 화합물.
- 청구항 5에 있어서, 상기 R32 및 R33은 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 실릴기; 치환 또는 비치환된 탄소수 6 내지 40의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 40의 헤테로아릴기이고, R32 및 R33의 중수소의 함량은 0%인 헤테로고리 화합물.
- 제1 전극, 제2 전극 및 상기 제1 전극과 제2 전극 사이에 구비된 1층 이상의 유기물층을 포함하고, 상기 유기물층 중 1층 이상은 청구항 1 내지 8 중 어느 하나의 항에 따른 헤테로고리 화합물을 포함하는 것인 유기 발광 소자.
- 청구항 9에 있어서, 상기 유기물층은 1층 이상의 발광층을 포함하고, 상기 발광층은 상기 헤테로고리 화합물을 포함하는 것인 유기 발광 소자.
- 청구항 10에 있어서, 상기 발광층은 호스트 물질을 포함하며, 상기 호스트 물질은 상기 헤테로고리 화합물을 포함하는 것인 유기 발광 소자.
- 청구항 9에 있어서, 상기 유기 발광 소자는 발광층, 정공 주입층, 정공 수송층, 전자 주입층, 전자 수송층, 정공 보조층 및 정공 저지층으로 이루어진 군에서 선택되는 1층 또는 2층 이상을 더 포함하는 것인 유기 발광 소자.
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EP4231804A3 (en) * | 2022-02-16 | 2023-09-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
WO2024078287A1 (zh) * | 2022-10-09 | 2024-04-18 | 北京莱特众成光电材料科技有限公司 | 有机化合物、有机电致发光器件和电子装置 |
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KR102283849B1 (ko) * | 2020-08-21 | 2021-08-02 | 롬엔드하스전자재료코리아유한회사 | 유기 전계 발광 화합물, 복수 종의 호스트 재료 및 이를 포함하는 유기 전계 발광 소자 |
EP4060758A3 (en) | 2021-02-26 | 2023-03-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
JPWO2022255241A1 (ko) * | 2021-05-31 | 2022-12-08 | ||
EP4349812A1 (en) * | 2021-05-31 | 2024-04-10 | NIPPON STEEL Chemical & Material Co., Ltd. | Deuteride and organic electroluminescent element |
WO2022255242A1 (ja) * | 2021-05-31 | 2022-12-08 | 日鉄ケミカル&マテリアル株式会社 | 重水素化物及び有機電界発光素子 |
KR20230117775A (ko) | 2022-02-03 | 2023-08-10 | 주식회사 엘지에너지솔루션 | 배터리 관리 장치 및 방법 |
KR20240009224A (ko) * | 2022-07-13 | 2024-01-22 | 엘티소재주식회사 | 헤테로고리 화합물, 이를 포함하는 유기 발광 소자, 이의 제조 방법 및 유기 발광 소자의 유기물층용 조성물 |
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- 2021-07-21 JP JP2022578975A patent/JP2023537660A/ja active Pending
- 2021-07-21 US US18/011,925 patent/US20230337533A1/en active Pending
- 2021-07-21 WO PCT/KR2021/009383 patent/WO2022025515A1/ko active Application Filing
- 2021-07-21 CN CN202180061380.8A patent/CN116234805A/zh active Pending
- 2021-07-21 EP EP21849867.3A patent/EP4190778A1/en active Pending
- 2021-07-21 EP EP21850588.1A patent/EP4190779A1/en active Pending
- 2021-07-21 WO PCT/KR2021/009386 patent/WO2022025516A1/ko active Application Filing
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EP4231804A3 (en) * | 2022-02-16 | 2023-09-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
WO2024078287A1 (zh) * | 2022-10-09 | 2024-04-18 | 北京莱特众成光电材料科技有限公司 | 有机化合物、有机电致发光器件和电子装置 |
Also Published As
Publication number | Publication date |
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EP4190779A1 (en) | 2023-06-07 |
EP4190778A1 (en) | 2023-06-07 |
KR20220013910A (ko) | 2022-02-04 |
CN116234805A (zh) | 2023-06-06 |
KR20220013909A (ko) | 2022-02-04 |
CN116134033A (zh) | 2023-05-16 |
JP2023537660A (ja) | 2023-09-05 |
WO2022025515A1 (ko) | 2022-02-03 |
TW202214819A (zh) | 2022-04-16 |
TW202214818A (zh) | 2022-04-16 |
US20230247902A1 (en) | 2023-08-03 |
KR102562015B1 (ko) | 2023-08-01 |
US20230337533A1 (en) | 2023-10-19 |
JP2023535546A (ja) | 2023-08-18 |
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