JP2021073177A - 新規なヘテロ環式化合物およびこれを利用した有機発光素子 - Google Patents
新規なヘテロ環式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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- JP2021073177A JP2021073177A JP2020210801A JP2020210801A JP2021073177A JP 2021073177 A JP2021073177 A JP 2021073177A JP 2020210801 A JP2020210801 A JP 2020210801A JP 2020210801 A JP2020210801 A JP 2020210801A JP 2021073177 A JP2021073177 A JP 2021073177A
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- 150000002391 heterocyclic compounds Chemical class 0.000 title abstract description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 520
- 125000003118 aryl group Chemical group 0.000 claims abstract description 41
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 7
- 239000010410 layer Substances 0.000 claims description 117
- 239000000126 substance Substances 0.000 claims description 96
- 229910052757 nitrogen Inorganic materials 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 239000012044 organic layer Substances 0.000 claims description 20
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
- 229910052805 deuterium Inorganic materials 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 125000005842 heteroatom Chemical group 0.000 claims description 9
- 239000011368 organic material Substances 0.000 claims description 9
- 125000001188 haloalkyl group Chemical group 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000000732 arylene group Chemical group 0.000 claims description 4
- 125000006653 (C1-C20) heteroaryl group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 125000005549 heteroarylene group Chemical group 0.000 claims description 3
- 229910052710 silicon Inorganic materials 0.000 claims description 3
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 2
- 125000004957 naphthylene group Chemical group 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 abstract description 13
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 abstract description 10
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 abstract description 4
- 125000004306 triazinyl group Chemical group 0.000 abstract description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 3
- 125000004076 pyridyl group Chemical group 0.000 abstract description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 description 306
- 238000003786 synthesis reaction Methods 0.000 description 305
- 238000004519 manufacturing process Methods 0.000 description 159
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 81
- -1 heterocyclic compound compound Chemical class 0.000 description 81
- SQTPFYJEKHTINP-UHFFFAOYSA-N 2-bromophenanthrene Chemical compound C1=CC=C2C3=CC=C(Br)C=C3C=CC2=C1 SQTPFYJEKHTINP-UHFFFAOYSA-N 0.000 description 75
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 57
- 239000000203 mixture Substances 0.000 description 57
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 48
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 38
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 30
- 238000002347 injection Methods 0.000 description 29
- 239000007924 injection Substances 0.000 description 29
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 26
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 25
- 238000002360 preparation method Methods 0.000 description 24
- OHVLMTFVQDZYHP-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CN1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O OHVLMTFVQDZYHP-UHFFFAOYSA-N 0.000 description 23
- 125000004432 carbon atom Chemical group C* 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 23
- DDGPPAMADXTGTN-UHFFFAOYSA-N 2-chloro-4,6-diphenyl-1,3,5-triazine Chemical compound N=1C(Cl)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 DDGPPAMADXTGTN-UHFFFAOYSA-N 0.000 description 22
- 238000000034 method Methods 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 18
- 230000032258 transport Effects 0.000 description 18
- WZFUQSJFWNHZHM-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 WZFUQSJFWNHZHM-UHFFFAOYSA-N 0.000 description 16
- 230000000052 comparative effect Effects 0.000 description 16
- 239000000463 material Substances 0.000 description 16
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 239000007787 solid Substances 0.000 description 14
- 239000000758 substrate Substances 0.000 description 14
- 239000002253 acid Substances 0.000 description 13
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 13
- 230000005525 hole transport Effects 0.000 description 13
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 13
- 235000019341 magnesium sulphate Nutrition 0.000 description 13
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 12
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 12
- 229910052782 aluminium Inorganic materials 0.000 description 10
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 125000000623 heterocyclic group Chemical group 0.000 description 9
- 0 *1c(c(-c2ccccc2)ccc2)c2-c2ccccc12 Chemical compound *1c(c(-c2ccccc2)ccc2)c2-c2ccccc12 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000002019 doping agent Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- DCHUWNPMFFVAHE-UHFFFAOYSA-N BrC1=CC=2C=CC3=CC=CC=C3C2C=C1.BrC1=CC=2C=CC3=CC=CC=C3C2C=C1 Chemical compound BrC1=CC=2C=CC3=CC=CC=C3C2C=C1.BrC1=CC=2C=CC3=CC=CC=C3C2C=C1 DCHUWNPMFFVAHE-UHFFFAOYSA-N 0.000 description 7
- 125000003342 alkenyl group Chemical group 0.000 description 7
- 238000000151 deposition Methods 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- PXFBSZZEOWJJNL-UHFFFAOYSA-N triphenylen-2-ylboronic acid Chemical compound C1=CC=C2C3=CC(B(O)O)=CC=C3C3=CC=CC=C3C2=C1 PXFBSZZEOWJJNL-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 235000011056 potassium acetate Nutrition 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 5
- 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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 150000004982 aromatic amines Chemical class 0.000 description 5
- 239000010406 cathode material Substances 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- 230000008021 deposition Effects 0.000 description 5
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 5
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 4
- SDUAXSKHZIJCSC-UHFFFAOYSA-N 4-chlorophenanthrene Chemical compound C1=CC=CC2=C3C(Cl)=CC=CC3=CC=C21 SDUAXSKHZIJCSC-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 4
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 4
- 238000007740 vapor deposition Methods 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 239000010405 anode material Substances 0.000 description 3
- 125000001769 aryl amino group Chemical group 0.000 description 3
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 3
- 125000006267 biphenyl group Chemical group 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 229940125810 compound 20 Drugs 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 125000004185 ester group Chemical group 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- IOMMMLWIABWRKL-WUTDNEBXSA-N nazartinib Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1N1C2=C(Cl)C=CC=C2N=C1NC(=O)C1=CC=NC(C)=C1 IOMMMLWIABWRKL-WUTDNEBXSA-N 0.000 description 3
- 239000005416 organic matter Substances 0.000 description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 3
- 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 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 150000003852 triazoles Chemical group 0.000 description 3
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 3
- UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 description 2
- 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 2
- ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 description 2
- 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 2
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- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 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
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
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- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 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
- 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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- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
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- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D—HETEROCYCLIC COMPOUNDS
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- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
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- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
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Abstract
Description
本出願は、2016年7月20日付韓国特許出願第10−2016−0092202号、および2017年6月14日付韓国特許出願第10−2017−0075029号に基づいた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すべての内容は本明細書の一部として組み含まれる。
[化学式1]
X1はOまたはSであり、
L1およびL2は、それぞれ独立に、単一結合;置換もしくは非置換のC6−60アリーレン;または置換もしくは非置換のO、N、SiおよびSから構成される群より選択されるヘテロ原子を1個以上含むC1−60ヘテロアリーレンであり、
Y1からY3は、それぞれ独立に、NまたはCR3であって、Y1からY3のうちの少なくとも一つはNであり、
Ar1aおよびAr1bは、それぞれ独立に、置換もしくは非置換のC6−60アリール;または置換もしくは非置換のN、OおよびSから構成される群より選択されるヘテロ原子を1個から3個含むC1−60ヘテロアリールであり、
Ar2は置換もしくは非置換のC6−60アリールであり、
R1からR3は、それぞれ独立に、水素;重水素;ハロゲン;シアノ;ニトロ;アミノ;置換もしくは非置換のC1−60アルキル;置換もしくは非置換のC1−60ハロアルキル;置換もしくは非置換のC1−60アルコキシ;置換もしくは非置換のC1−60ハロアルコキシ;置換もしくは非置換のC3−60シクロアルキル;置換もしくは非置換のC2−60アルケニル;置換もしくは非置換のC6−60アリール;置換もしくは非置換のC6−60アリールオキシ;または置換もしくは非置換のN、OおよびSから構成される群より選択されるヘテロ原子を1個以上含むC1−60ヘテロアリールであり、
n1およびn2は、それぞれ独立に、0から3の整数である。
[化学式1−1]
Y1はNであり、Y2はNであり、Y3はNであるか;
Y1はNであり、Y2はNであり、Y3はCR3であるか;
Y1はNであり、Y2はCR3であり、Y3はNであるか;
Y1はNであり、Y2はCR3であり、Y3はCR3であるか;または
Y1はCR3であり、Y2はCR3であり、Y3はNであってもよい。
Y1はNであり、Y2はNであり、Y3はNであるか;
Y1はNであり、Y2はNであり、Y3はCHであるか;
Y1はNであり、Y2はCHであり、Y3はNであるか;
Y1はNであり、Y2はCHであり、Y3はCHであるか;または
Y1はCHであり、Y2はCHであり、Y3はNであってもよい。
X2はO、S、NZ4、またはCZ5Z6であり、
Z1からZ6は、それぞれ独立に、水素;重水素;ハロゲン;シアノ;ニトロ;アミノ;置換もしくは非置換のC1−20アルキル;置換もしくは非置換のC1−20ハロアルキル;置換もしくは非置換のC6−20アリール;または置換もしくは非置換のN、OおよびSから構成される群より選択されるヘテロ原子を1個以上含むC1−20ヘテロアリールであり、
c1は0から5の整数であり、
c2は0から4の整数であり、
c3は0から3の整数である。
ここで、Q1からQ6は、それぞれ独立に、水素;重水素;ハロゲン;シアノ;ニトロ;アミノ;置換もしくは非置換のC1−20アルキル;または置換もしくは非置換のC6−20アリールであってもよい。
ここで、Q1からQ6は、それぞれ独立に、水素;重水素;ハロゲン;シアノ;ニトロ;アミノ;置換もしくは非置換のC1−20アルキル;または置換もしくは非置換のC6−20アリールであり、
c11は0から5の整数であり、
c12は0から7の整数であり、
c13は0から9の整数であり、
c14は0から4の整数であり、
c15は0から3の整数であり、
c16は0から11の整数であり、
c17は0から9の整数であり、
c18は0から6の整数であり、
c19は0から12の整数である。
[反応式1]
ITO(indium tin oxide)が1,300Å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溜水に入れて超音波で洗浄した。この時、洗剤としてはフィッシャー社(Fischer Co.)製品を用い、蒸溜水としてはミリポア社(Millipore Co.)製品のフィルター(Filter)で2次濾過された蒸留水を用いた。ITOを30分間洗浄した後、蒸溜水で2回繰り返して超音波洗浄を10分間行った。蒸溜水洗浄が終わった後、イソプロピルアルコール、アセトン、メタノールの溶剤で超音波洗浄を行い、乾燥させた後、プラズマ洗浄機に輸送させた。また、酸素プラズマを利用して前記基板を5分間洗浄した後、真空蒸着器に基板を輸送させた。
発光層の形成時、燐光ホスト物質およびドーパント含有量を下記表1から3のように変更した点を除いては、前記実施例1と同様な方法を利用して実施例2から49の有機発光素子をそれぞれ製作した。
発光層の形成時、燐光ホスト物質およびドーパント含有量を下記表3のように変更した点を除いては、前記実施例1と同様な方法を利用して比較例1から10の有機発光素子をそれぞれ製作した。この時、比較例に用いられたホスト物質AからIは下記のとおりである。
前記実施例1から49および比較例1から10で製作された有機発光素子に電流を印加し、電圧、効率、輝度、色座標および寿命を測定し、その結果を下記表1から3に示した。この時、T95は光密度50mA/cm2での初期輝度を100%にした時、輝度が95%に減少するのにかかる時間を意味する。
前記実施例1のように準備されたITO透明電極上に下記のようなHI−1化合物を150Åの厚さに熱真空蒸着して正孔注入層を形成した。
発光層の形成時、燐光ホスト物質およびドーパント含有量を下記表4および5のように変更した点を除いては、前記実施例50と同様な方法を利用して実施例51から90の有機発光素子をそれぞれ製作した。
発光層の形成時、燐光ホスト物質およびドーパント含有量を下記表6のように変更した点を除いては、前記実施例50と同様な方法を利用して比較例11から19の有機発光素子をそれぞれ製作した。この時、比較例に用いられたホスト物質AからIは前述のとおりである。
前記実施例50から90および比較例11から19で製作された有機発光素子に電流を印加し、電圧、効率、輝度、色座標および寿命を測定し、その結果を下記表4から6に示した。この時、T95は光密度20mA/cm2での初期輝度を100%にした時、輝度が95%に減少するのにかかる時間を意味する。
2:陽極
3:発光層
4:陰極
5:正孔注入層
6:正孔輸送層
7:発光層
8:電子輸送層
Claims (13)
- 下記の化学式1で表される化合物:
[化学式1]
X1はOまたはSであり、
L1およびL2は、それぞれ独立に、単一結合;置換もしくは非置換のC6−60アリーレン;または置換もしくは非置換のO、N、SiおよびSから構成される群より選択されるヘテロ原子を1個以上含むC1−60ヘテロアリーレンであり、
Y1からY3は、それぞれ独立に、NまたはCR3であって、Y1からY3のうちの少なくとも一つはNであり、
Ar1aおよびAr1bは、それぞれ独立に、置換もしくは非置換のC6−60アリール;または置換もしくは非置換のN、OおよびSから構成される群より選択されるヘテロ原子を1個から3個含むC1−60ヘテロアリールであり、
Ar2は置換もしくは非置換のC6−60アリールであり、
R1からR3は、それぞれ独立に、水素;重水素;ハロゲン;シアノ;ニトロ;アミノ;置換もしくは非置換のC1−60アルキル;置換もしくは非置換のC1−60ハロアルキル;置換もしくは非置換のC1−60アルコキシ;置換もしくは非置換のC1−60ハロアルコキシ;置換もしくは非置換のC3−60シクロアルキル;置換もしくは非置換のC2−60アルケニル;置換もしくは非置換のC6−60アリール;置換もしくは非置換のC6−60アリールオキシ;または置換もしくは非置換のN、OおよびSから構成される群より選択されるヘテロ原子を1個以上含むC1−60ヘテロアリールであり、
n1およびn2は、それぞれ独立に、0から3の整数である。 - L1およびL2は、それぞれ独立に、単一結合;置換もしくは非置換のフェニレン;置換もしくは非置換のナフチレン;または置換もしくは非置換のビフェニリレンである、請求項1に記載の化合物。
- Y1はNであり、Y2はNであり、Y3はNであるか;
Y1はNであり、Y2はNであり、Y3はCHであるか;
Y1はNであり、Y2はCHであり、Y3はNであるか;
Y1はNであり、Y2はCHであり、Y3はCHであるか;または
Y1はCHであり、Y2はCHであり、Y3はNである、請求項1から3のいずれか一項に記載の化合物。 - Ar1aおよびAr1bは、それぞれ独立に、下記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から4のいずれか一項に記載の化合物:
X2はO、S、NZ4、またはCZ5Z6であり、
Z1からZ6は、それぞれ独立に、水素;重水素;ハロゲン;シアノ;ニトロ;アミノ;置換もしくは非置換のC1−20アルキル;置換もしくは非置換のC1−20ハロアルキル;置換もしくは非置換のC6−20アリール;または置換もしくは非置換のN、OおよびSから構成される群より選択されるヘテロ原子を1個以上含むC1−20ヘテロアリールであり、
c1は0から5の整数であり、
c2は0から4の整数であり、
c3は0から3の整数である。 - Ar2は下記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から6のいずれか一項に記載の化合物:
Z11からZ14は、それぞれ独立に、水素;重水素;ハロゲン;シアノ;ニトロ;アミノ;置換もしくは非置換のC1−60アルキル;置換もしくは非置換のC1−60ハロアルキル;Si(Q1)(Q2)(Q3);C(Q4)(Q5)(Q6)およびC6−60アリールであり、
ここで、Q1からQ6は、それぞれ独立に、水素;重水素;ハロゲン;シアノ;ニトロ;アミノ;置換もしくは非置換のC1−20アルキル;または置換もしくは非置換のC6−20アリールであり、
c11は0から5の整数であり、
c12は0から7の整数であり、
c13は0から9の整数であり、
c14は0から4の整数であり、
c15は0から3の整数であり、
c16は0から11の整数であり、
c17は0から9の整数であり、
c18は0から6の整数であり、
c19は0から12の整数である。 - R1およびR2は、それぞれ独立に、水素;重水素;シアノ;または置換もしくは非置換のC1−10アルキルである、請求項1から8のいずれか一項に記載の化合物。
- 第1電極;前記第1電極と対向して備えられた第2電極;および前記第1電極と前記第2電極との間に備えられた1層以上の有機物層を含む有機発光素子であって、前記有機物層のうちの1層以上は、請求項1から10のいずれか一項に記載の化合物を含むものである、有機発光素子。
- 前記化合物を含む有機物層は、発光層である、請求項11に記載の有機発光素子。
- 前記化合物は、ホスト物質として用いられる、請求項12に記載の有機発光素子。
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US20220336757A1 (en) | 2022-10-20 |
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