JP7427318B2 - 新規な化合物およびこれを利用した有機発光素子 - Google Patents
新規な化合物およびこれを利用した有機発光素子 Download PDFInfo
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- JP7427318B2 JP7427318B2 JP2022551367A JP2022551367A JP7427318B2 JP 7427318 B2 JP7427318 B2 JP 7427318B2 JP 2022551367 A JP2022551367 A JP 2022551367A JP 2022551367 A JP2022551367 A JP 2022551367A JP 7427318 B2 JP7427318 B2 JP 7427318B2
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- 150000001875 compounds Chemical class 0.000 title claims description 260
- 125000004432 carbon atom Chemical group C* 0.000 claims description 87
- -1 dibenzofuranyl Chemical group 0.000 claims description 53
- 239000000126 substance Substances 0.000 claims description 51
- 125000003118 aryl group Chemical group 0.000 claims description 45
- 125000001424 substituent group Chemical group 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 22
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 21
- 229910052805 deuterium Inorganic materials 0.000 claims description 21
- 229910052760 oxygen Inorganic materials 0.000 claims description 19
- 125000001072 heteroaryl group Chemical group 0.000 claims description 17
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- 125000005842 heteroatom Chemical group 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 9
- 125000000732 arylene group Chemical group 0.000 claims description 8
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 150000002431 hydrogen Chemical group 0.000 claims description 5
- 125000004957 naphthylene group Chemical group 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 239000010410 layer Substances 0.000 description 99
- 230000015572 biosynthetic process Effects 0.000 description 62
- 238000003786 synthesis reaction Methods 0.000 description 62
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 40
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 38
- 238000002347 injection Methods 0.000 description 33
- 239000007924 injection Substances 0.000 description 33
- 239000000243 solution Substances 0.000 description 33
- 238000004519 manufacturing process Methods 0.000 description 31
- 239000000463 material Substances 0.000 description 24
- 239000002244 precipitate Substances 0.000 description 24
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 23
- 238000000034 method Methods 0.000 description 23
- 230000032258 transport Effects 0.000 description 22
- 239000012044 organic layer Substances 0.000 description 21
- 239000002904 solvent Substances 0.000 description 20
- 230000000052 comparative effect Effects 0.000 description 19
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 19
- 239000000377 silicon dioxide Substances 0.000 description 19
- 239000012065 filter cake Substances 0.000 description 18
- 230000008569 process Effects 0.000 description 18
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 17
- 229910052799 carbon Inorganic materials 0.000 description 16
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 238000005406 washing Methods 0.000 description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 14
- 238000004440 column chromatography Methods 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 13
- 239000000758 substrate Substances 0.000 description 13
- 239000008199 coating composition Substances 0.000 description 12
- 230000005525 hole transport Effects 0.000 description 12
- 238000010438 heat treatment Methods 0.000 description 11
- 230000000903 blocking effect Effects 0.000 description 10
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000011368 organic material Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 125000003342 alkenyl group Chemical group 0.000 description 7
- 239000002019 doping agent Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 6
- 229940125904 compound 1 Drugs 0.000 description 6
- 125000000623 heterocyclic group Chemical group 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 125000000753 cycloalkyl group Chemical group 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000151 deposition Methods 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 4
- 125000002950 monocyclic group Chemical group 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- 125000003367 polycyclic group Chemical group 0.000 description 4
- 239000007774 positive electrode material Substances 0.000 description 4
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 3
- 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 3
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 3
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 3
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 3
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 3
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 229940126657 Compound 17 Drugs 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- 238000006069 Suzuki reaction reaction Methods 0.000 description 3
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 3
- LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
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- 150000001412 amines Chemical group 0.000 description 3
- 150000004982 aromatic amines Chemical class 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000006267 biphenyl group Chemical group 0.000 description 3
- 229940125797 compound 12 Drugs 0.000 description 3
- 229940126543 compound 14 Drugs 0.000 description 3
- 229940125758 compound 15 Drugs 0.000 description 3
- 229940126142 compound 16 Drugs 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 239000007773 negative electrode material Substances 0.000 description 3
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- 150000003852 triazoles Chemical group 0.000 description 3
- 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 description 2
- UVNPEUJXKZFWSJ-LMTQTHQJSA-N (R)-N-[(4S)-8-[6-amino-5-[(3,3-difluoro-2-oxo-1H-pyrrolo[2,3-b]pyridin-4-yl)sulfanyl]pyrazin-2-yl]-2-oxa-8-azaspiro[4.5]decan-4-yl]-2-methylpropane-2-sulfinamide Chemical compound CC(C)(C)[S@@](=O)N[C@@H]1COCC11CCN(CC1)c1cnc(Sc2ccnc3NC(=O)C(F)(F)c23)c(N)n1 UVNPEUJXKZFWSJ-LMTQTHQJSA-N 0.000 description 2
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 2
- UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 2
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 2
- YWDUZLFWHVQCHY-UHFFFAOYSA-N 1,3,5-tribromobenzene Chemical compound BrC1=CC(Br)=CC(Br)=C1 YWDUZLFWHVQCHY-UHFFFAOYSA-N 0.000 description 2
- DPZNOMCNRMUKPS-UHFFFAOYSA-N 1,3-Dimethoxybenzene Chemical compound COC1=CC=CC(OC)=C1 DPZNOMCNRMUKPS-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
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- 125000005916 2-methylpentyl group Chemical group 0.000 description 2
- WDBQJSCPCGTAFG-QHCPKHFHSA-N 4,4-difluoro-N-[(1S)-3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-pyridin-3-ylpropyl]cyclohexane-1-carboxamide Chemical compound FC1(CCC(CC1)C(=O)N[C@@H](CCN1CCC(CC1)N1C(=NN=C1C)C(C)C)C=1C=NC=CC=1)F WDBQJSCPCGTAFG-QHCPKHFHSA-N 0.000 description 2
- BWGRDBSNKQABCB-UHFFFAOYSA-N 4,4-difluoro-N-[3-[3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-thiophen-2-ylpropyl]cyclohexane-1-carboxamide Chemical compound CC(C)C1=NN=C(C)N1C1CC2CCC(C1)N2CCC(NC(=O)C1CCC(F)(F)CC1)C1=CC=CS1 BWGRDBSNKQABCB-UHFFFAOYSA-N 0.000 description 2
- DDTHMESPCBONDT-UHFFFAOYSA-N 4-(4-oxocyclohexa-2,5-dien-1-ylidene)cyclohexa-2,5-dien-1-one Chemical compound C1=CC(=O)C=CC1=C1C=CC(=O)C=C1 DDTHMESPCBONDT-UHFFFAOYSA-N 0.000 description 2
- ZYASLTYCYTYKFC-UHFFFAOYSA-N 9-methylidenefluorene Chemical compound C1=CC=C2C(=C)C3=CC=CC=C3C2=C1 ZYASLTYCYTYKFC-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
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- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical group C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
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- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 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
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
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- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Description
本出願は、2020年3月3日付の韓国特許出願第10-2020-0026669号に基づく優先権の利益を主張し、当該韓国特許出願の文献に開示された全ての内容は本明細書の一部として含まれる。
LはN;C(Z1);置換または非置換の3価の炭素数6~60の芳香族環;または置換または非置換のN、OおよびSのうちの1個以上のヘテロ原子を含む3価の炭素数2~60のヘテロ芳香族環であり、
L’はそれぞれ独立して、単結合;O;S;N(Z2);または置換または非置換の炭素数6~60のアリーレンであり、
nは0、1または2であり、
ここで、Z1およびZ2はそれぞれ独立して、水素;重水素;置換または非置換の炭素数1~60のアルキル;置換または非置換の炭素数6~60のアリール;または置換または非置換のN、OおよびSのうちの1個以上のヘテロ原子を含む炭素数2~60のヘテロアリールであり、
L1~L3はそれぞれ独立して、単結合;置換または非置換の炭素数6~60のアリーレン;または置換または非置換のN、OおよびSのうちの1個以上のヘテロ原子を含む炭素数2~60のヘテロアリーレンであり、
Ar1~Ar3はそれぞれ独立して、置換または非置換の炭素数6~60のアリール;または置換または非置換のN、OおよびSのうちの1個以上のヘテロ原子を含む炭素数2~60のヘテロアリールであり、
R1~R3はそれぞれ独立して、水素;重水素;ハロゲン;シアノ;置換または非置換の炭素数1~60のアルキル;置換または非置換の炭素数6~60のアリール;または置換または非置換のN、OおよびSのうちの1個以上のヘテロ原子を含む炭素数2~60のヘテロアリールであり、
aおよびcはそれぞれ独立して、0~3の整数であり、
bは0~4の整数であり、
n、a、bおよびcが2以上の場合、括弧内の置換基は互いに同一または異なり、
3つの角括弧「[]」内の構造は互いに同一または異なる。
本発明は、前記化学式1で表される化合物を提供する。
各置換基に対する説明は前記化学式1で定義した通りである。
各置換基に対する説明は上述した通りであり、
Lの左側に位置するL’は1a位の炭素、2a位の炭素、3a位の炭素および4a位の炭素のうちのいずれか一つと結合することができ、
Lの上側に位置するL’は1b位の炭素、2b位の炭素、3b位の炭素および4b位の炭素のうちのいずれか一つと結合することができ、
Lの右側に位置するL’は1c位の炭素、2c位の炭素、3c位の炭素および4c位の炭素のうちのいずれか一つと結合することができる。
L、L’、n、L1~L3、Ar1~Ar3、R1~R3、a、bおよびcは前記化学式1で定義した通りである。
L’はそれぞれ独立して、単結合;O;S;N(Z2);または置換または非置換の炭素数6~60のアリーレンであり、nは0、1または2である。
Lが置換または非置換の3価の炭素数6~60の芳香族環、または置換または非置換のN、OおよびSのうちの1個以上のヘテロ原子を含む3価の炭素数2~60のヘテロ芳香族環であれば、nは0、1または2である。
L’はそれぞれ独立して、単結合;O;S;N(Z2);または置換または非置換の炭素数6~60のアリーレンであり、
ここで、Z1およびZ2はそれぞれ独立して、水素;重水素;炭素数1~10のアルキル;非置換であるか、または重水素および炭素数1~10のアルキルから構成される群より選択される1個以上の置換基で置換された炭素数6~20のアリール;または非置換であるか、または重水素および炭素数1~10のアルキルから構成される群より選択される1個以上の置換基で置換されたN、OおよびSのうちの1個以上のヘテロ原子を含む炭素数2~20のヘテロアリールであり得る。
Lは3価の炭素数6~20の芳香族環であり、Lは3価の炭素数6~20の芳香族環であり、nは0、1または2であり得る。
Lは3価のベンゼン環、または3価のナフチレン環であり、L’は、nは1または2であり得る。
L3は単結合、フェニレン、またはナフチレンであり得る。
Ar3は非置換であるか、または重水素、メチル、tert-ブチル、フェニルおよびSi(フェニル)3から構成される群より選択される1個の置換基で置換されたフェニル;ジメチルフルオレニル;フェニルカルバゾリル;ジベンゾフラニル;ジベンゾチオフェニル;ベンゾフラニル;またはベンゾチオフェニルであり得る。
L’は互いに同一であってもよく、nは互いに同一であってもよく、L1は互いに同一であってもよく、L2は互いに同一であってもよく、L3は互いに同一であってもよく、Ar1は互いに同一であってもよく、Ar2は互いに同一であってもよく、Ar3は互いに同一であってもよく、R1は互いに同一であってもよく、R2は互いに同一であってもよく、R3は互いに同一であってもよく、aは互いに同一であってもよく、bは互いに同一であってもよく、cは互いに同一であってもよい。
L、L’、n、L1~L3およびAr1~Ar3は前記化学式1で定義した通りである。
L1~L3およびAr1~Ar3は前記化学式1で定義した通りである、
-(L’)n-は下記で構成される群より選択されるいずれか一つである。
一方、本発明に係る化合物は、溶液工程で有機発光素子の有機物層、特に発光層を形成することができる。具体的には、前記化合物は発光層のドーパント材料として用いられる。そのため、本発明は上述した本発明に係る化合物および溶媒を含むコーティング組成物を提供する。
また、本発明は、前記化学式1で表される化合物を含む有機発光素子を提供する。一例として、本発明は、第1電極と、前記第1電極に対向して備えられた第2電極と、前記第1電極と前記第2電極との間に備えられた発光層とを含む有機発光素子であって、前記発光層は、前記化学式1で表される化合物を含む有機発光素子を提供する。
m/z[M+H]+=425
m/z[M+H]+=381
m/z[M+H]+=439
m/z[M+H]+=375
m/z[M+H]+=527
m/z[M+H]+=274
m/z[M+H]+=764
m/z[M+H]+=2200
m/z[M+H]+=772
m/z[M+H]+=2995
m/z[M+H]+=461
m/z[M+H]+=951
m/z[M+H]+=2761
m/z[M+H]+=457
m/z[M+H]+=2261
m/z[M+H]+=2285
m/z[M+H]+=2822
m/z[M+H]+=352
m/z[M+H]+=749
m/z[M+H]+=2930
m/z[M+H]+=2955
m/z[M+H]+=3491
m/z[M+H]+=352
m/z[M+H]+=749
m/z[M+H]+=2930
m/z[M+H]+=520
m/z[M+H]+=2702
m/z[M+H]+=2726
m/z[M+H]+=3263
m/z[M+H]+=2309
m/z[M+H]+=355
m/z[M+H]+=2537
m/z[M+H]+=355
m/z[M+H]+=2537
m/z[M+H]+=439
m/z[M+H]+=375
m/z[M+H]+=527
m/z[M+H]+=764
m/z[M+H]+=2200
m/z[M+H]+=439
m/z[M+H]+=375
m/z[M+H]+=527
m/z[M+H]+=764
m/z[M+H]+=1605
m/z[M+H]+=439
m/z[M+H]+=375
m/z[M+H]+=527
m/z[M+H]+=764
m/z[M+H]+=1605
m/z[M+H]+=1001
m/z[M+H]+=1018
m/z[M+H]+=1376
m/z[M+H]+=1258
前記製造例で製造した化合物および比較化合物の溶液工程に用いられる溶媒に対する溶解度を確認するために、これらをそれぞれ溶媒シクロヘキサノン(CHON)に常温/常圧条件で溶解した後、0.1wt%以上溶解するか否かを確認し、その結果を表1に示す。
実施例1
ITO(indium tin oxide)が500Åの厚さに薄膜コーティングされたガラス基板を洗剤を溶かした蒸留水に入れて超音波洗浄した。この時、洗剤としてはフィッシャー社(Fischer Co.)製品を使用し、蒸留水としてはミリポア社(Millipore Co.)製品のフィルタ(Filter)で2次ろ過した蒸留水を使用した。ITOを30分間洗浄した後、蒸留水で2回繰り返し超音波洗浄を10分間進行した。蒸留水洗浄が終わった後、イソプロピルアルコール、アセトンの溶剤で超音波洗浄をし、乾燥させた後、前記基板を5分間洗浄した後、グローブボックスに基板を輸送させた。
発光層のドーパントとして化合物1の代わりに下記表2に記載された化合物を使用したことを除いて、前記実施例1と同様の方法で有機発光素子を製造した。
発光層のドーパントとして化合物1の代わりに下記表2に記載された化合物を使用したことを除いて、前記実施例1と同様の方法で有機発光素子を製造した。
前記実施例および比較例で製造した有機発光素子に電流を印加したとき、10mA/cm2の電流密度での駆動電圧、外部量子効率(external quantum efficiency、EQE)および寿命を測定した結果を下記表2に示す。このとき、外部量子効率(EQE)は、「(放出された光子数)/(注入された電荷運搬体数)×100」から求め、T90は、初期輝度(500nit)が90%に低下するまでの時間を意味する。
2 正極
3 発光層
4 負極
5 正孔注入層
6 正孔輸送層
7 電子注入および輸送層
Claims (12)
- 下記化学式1で表される化合物:
LはNまたは3価の炭素数6~60の芳香族環であり、
L’はそれぞれ独立して、単結合;O;S;N(Z2);または炭素数6~60のアリーレンであり、
nは0、1または2であり、
ここで、Z 2 は非置換であるか、または炭素数1~10のアルキル、ベンゾフラニルおよびベンゾチオフェニルから構成される群より選択される1個以上の置換基で置換されたフェニル;非置換であるか、または炭素数1~10のアルキル、ベンゾフラニルおよびベンゾチオフェニルから構成される群より選択される1個以上の置換基で置換されたナフチル;または非置換であるか、または炭素数1~10のアルキル、ベンゾフラニルおよびベンゾチオフェニルから構成される群より選択される1個以上の置換基で置換されたジベンゾフラニルであり、
L1~L3はそれぞれ独立して、単結合または炭素数6~60のアリーレンであり、
Ar1~Ar3はそれぞれ独立して、非置換であるか、または重水素、メチル、tert-ブチル、フェニルおよびSi(フェニル) 3 から構成される群より選択される1個以上の置換基で置換された炭素数6~20のアリール;または非置換であるか、または重水素、メチル、tert-ブチル、フェニルおよびSi(フェニル) 3 から構成される群より選択される1個以上の置換基で置換されたN、OおよびSのうちの1個のヘテロ原子を含む炭素数2~20のヘテロアリールであり、
R1~R3はそれぞれ独立して、水素または重水素であり、
aおよびcはそれぞれ独立して、0~3の整数であり、
bは0~4の整数である。 - 前記化合物は、下記化学式1-1~1-4のうちのいずれか一つで表される、請求項1に記載の化合物:
L、L’、n、L1~L3、Ar1~Ar3、R1~R3、a、bおよびcは請求項1で定義した通りである。 - LはNであり、nは0であるか;または
Lは3価の炭素数6~20の芳香族環であり、nは0、1または2である、請求項1に記載の化合物。 - LはN、または
- -(L’)n-は単結合、または下記で構成される群より選択されるいずれか一つである、請求項1に記載の化合物:
- L1~L3はそれぞれ独立して、単結合、フェニレン、またはナフチレンである、請求項1に記載の化合物。
- Ar1およびAr2はそれぞれ独立して、
ここで、Rは水素、メチル、またはtert-ブチルである、請求項1に記載の化合物。 - Ar3は、下記で構成される群より選択されるいずれか一つである、請求項1に記載の化合物:
- 3つの角括弧「[]」内の構造は互いに同じである、請求項1に記載の化合物。
- 前記化合物は、下記化学式1-1-1~1-4-1のうちのいずれか一つで表される、請求項1に記載の化合物:
L、L’、n、L1~L3およびAr1~Ar3は請求項1で定義した通りである。 - 前記化合物は、下記化合物から構成される群より選択されるいずれか一つである、請求項1に記載の化合物:
- 第1電極と、前記第1電極に対向して備えられた第2電極と、前記第1電極と前記第2電極との間に備えられた発光層とを含む有機発光素子であって、前記発光層は、請求項1~11のいずれか一項に記載の化合物を含む、有機発光素子。
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