WO2018110958A1 - Organic light-emitting compound and organic electroluminescent element using same - Google Patents
Organic light-emitting compound and organic electroluminescent element using same Download PDFInfo
- Publication number
- WO2018110958A1 WO2018110958A1 PCT/KR2017/014607 KR2017014607W WO2018110958A1 WO 2018110958 A1 WO2018110958 A1 WO 2018110958A1 KR 2017014607 W KR2017014607 W KR 2017014607W WO 2018110958 A1 WO2018110958 A1 WO 2018110958A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- aryl
- triazine
- chloro
- synthesis example
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 196
- 239000011368 organic material Substances 0.000 claims abstract description 20
- 238000000034 method Methods 0.000 claims description 134
- 125000003118 aryl group Chemical group 0.000 claims description 132
- -1 alkyl boron Chemical compound 0.000 claims description 83
- 125000000217 alkyl group Chemical group 0.000 claims description 62
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 47
- 125000004429 atom Chemical group 0.000 claims description 47
- 125000001424 substituent group Chemical group 0.000 claims description 41
- 125000001072 heteroaryl group Chemical group 0.000 claims description 40
- 125000003545 alkoxy group Chemical group 0.000 claims description 33
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 33
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 33
- 125000003342 alkenyl group Chemical group 0.000 claims description 32
- 125000005104 aryl silyl group Chemical group 0.000 claims description 32
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 30
- 125000000304 alkynyl group Chemical group 0.000 claims description 30
- 125000004104 aryloxy group Chemical group 0.000 claims description 28
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 24
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims description 24
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 22
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 22
- 229910052805 deuterium Inorganic materials 0.000 claims description 22
- 229910052736 halogen Inorganic materials 0.000 claims description 22
- 150000002367 halogens Chemical class 0.000 claims description 22
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 22
- 150000002431 hydrogen Chemical class 0.000 claims description 21
- 238000002347 injection Methods 0.000 claims description 21
- 239000007924 injection Substances 0.000 claims description 21
- 125000005264 aryl amine group Chemical group 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 239000000126 substance Substances 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 150000004982 aromatic amines Chemical class 0.000 claims description 10
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 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 claims description 6
- 125000000732 arylene group Chemical group 0.000 claims description 6
- 125000005549 heteroarylene group Chemical group 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 235000010290 biphenyl Nutrition 0.000 claims description 5
- 239000004305 biphenyl Substances 0.000 claims description 5
- 229910052796 boron Inorganic materials 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 3
- 229910052738 indium Inorganic materials 0.000 claims description 3
- 239000010977 jade Substances 0.000 claims description 3
- 125000006751 (C6-C60) aryloxy group Chemical group 0.000 claims description 2
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 description 491
- 238000003786 synthesis reaction Methods 0.000 description 491
- 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 161
- 239000010410 layer Substances 0.000 description 75
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 63
- 239000000463 material Substances 0.000 description 53
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 35
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 28
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 28
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 28
- KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 description 23
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 14
- 238000004440 column chromatography Methods 0.000 description 14
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 14
- OVNPUJOZNPAVJQ-UHFFFAOYSA-N 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine Chemical compound ClC1=CC=CC(C=2N=C(N=C(N=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 OVNPUJOZNPAVJQ-UHFFFAOYSA-N 0.000 description 10
- PJRGCJBBXGNEGD-UHFFFAOYSA-N 2-bromo-9h-carbazole Chemical compound C1=CC=C2C3=CC=C(Br)C=C3NC2=C1 PJRGCJBBXGNEGD-UHFFFAOYSA-N 0.000 description 9
- 239000002019 doping agent Substances 0.000 description 9
- 230000005525 hole transport Effects 0.000 description 9
- 239000012044 organic layer Substances 0.000 description 9
- SHXRJHODWWVKAQ-UHFFFAOYSA-N 2-chloro-4-dibenzofuran-2-yl-6-phenyl-1,3,5-triazine Chemical compound ClC1=NC(=NC(=N1)C1=CC2=C(OC3=C2C=CC=C3)C=C1)C1=CC=CC=C1 SHXRJHODWWVKAQ-UHFFFAOYSA-N 0.000 description 8
- MPIJGSAWPMMKMU-UHFFFAOYSA-N 2-chloro-4-dibenzofuran-3-yl-6-phenyl-1,3,5-triazine Chemical compound ClC1=NC(=NC(=N1)C=1C=CC2=C(OC3=C2C=CC=C3)C=1)C1=CC=CC=C1 MPIJGSAWPMMKMU-UHFFFAOYSA-N 0.000 description 8
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 8
- RTXODVRNOQIGIM-UHFFFAOYSA-N 4-chloro-6-phenyl-2-(4-phenylphenyl)pyrimidine Chemical compound C1(=CC=C(C=C1)C1=NC(=CC(=N1)Cl)C1=CC=CC=C1)C1=CC=CC=C1 RTXODVRNOQIGIM-UHFFFAOYSA-N 0.000 description 8
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 8
- PJJAZVKQILCJTF-UHFFFAOYSA-N ClC1=NC(=NC(=N1)C1=CC=CC2=C1C1=C(O2)C=CC=C1)C1=CC=CC=C1 Chemical compound ClC1=NC(=NC(=N1)C1=CC=CC2=C1C1=C(O2)C=CC=C1)C1=CC=CC=C1 PJJAZVKQILCJTF-UHFFFAOYSA-N 0.000 description 8
- JKHCVYDYGWHIFJ-UHFFFAOYSA-N Clc1nc(nc(n1)-c1ccc(cc1)-c1ccccc1)-c1ccccc1 Chemical compound Clc1nc(nc(n1)-c1ccc(cc1)-c1ccccc1)-c1ccccc1 JKHCVYDYGWHIFJ-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
- NKLKYZYRMGGYGN-UHFFFAOYSA-N 2-chloro-4-dibenzofuran-4-yl-6-phenyl-1,3,5-triazine Chemical compound ClC1=NC(=NC(=N1)C1=CC=CC2=C1OC1=C2C=CC=C1)C1=CC=CC=C1 NKLKYZYRMGGYGN-UHFFFAOYSA-N 0.000 description 7
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 7
- FDTRHTNHPKRWFG-UHFFFAOYSA-N 4-(3-chlorophenyl)-2,6-diphenylpyrimidine Chemical compound ClC=1C=C(C=CC=1)C1=NC(=NC(=C1)C1=CC=CC=C1)C1=CC=CC=C1 FDTRHTNHPKRWFG-UHFFFAOYSA-N 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 6
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000004020 luminiscence type Methods 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
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- 239000000758 substrate Substances 0.000 description 4
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 3
- 125000006575 electron-withdrawing group Chemical group 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
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- 125000005580 triphenylene group Chemical group 0.000 description 3
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 2
- 0 C*c(cc1)ccc1-c1ccccc1 Chemical compound C*c(cc1)ccc1-c1ccccc1 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- JUCOXJQKQCXDHE-UHFFFAOYSA-N Clc1cccc(-c2cc(-c3nc(-c(cc4)cc5c4c(cccc4)c4[o]5)nc(-c4ccccc4)n3)ccc2)c1 Chemical compound Clc1cccc(-c2cc(-c3nc(-c(cc4)cc5c4c(cccc4)c4[o]5)nc(-c4ccccc4)n3)ccc2)c1 JUCOXJQKQCXDHE-UHFFFAOYSA-N 0.000 description 2
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 2
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- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 2
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- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 2
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- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
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- KPTRDYONBVUWPD-UHFFFAOYSA-N naphthalen-2-ylboronic acid Chemical compound C1=CC=CC2=CC(B(O)O)=CC=C21 KPTRDYONBVUWPD-UHFFFAOYSA-N 0.000 description 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
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- HYCYKHYFIWHGEX-UHFFFAOYSA-N (2-phenylphenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1C1=CC=CC=C1 HYCYKHYFIWHGEX-UHFFFAOYSA-N 0.000 description 1
- MRBZYVMZUBUDAX-UHFFFAOYSA-N (3,5-diphenylphenyl)boronic acid Chemical compound C=1C(B(O)O)=CC(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 MRBZYVMZUBUDAX-UHFFFAOYSA-N 0.000 description 1
- GOXICVKOZJFRMB-UHFFFAOYSA-N (3-phenylphenyl)boronic acid Chemical compound OB(O)C1=CC=CC(C=2C=CC=CC=2)=C1 GOXICVKOZJFRMB-UHFFFAOYSA-N 0.000 description 1
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- XPEIJWZLPWNNOK-UHFFFAOYSA-N (4-phenylphenyl)boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C1=CC=CC=C1 XPEIJWZLPWNNOK-UHFFFAOYSA-N 0.000 description 1
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- ABDDQTDRAHXHOC-QMMMGPOBSA-N 1-[(7s)-5,7-dihydro-4h-thieno[2,3-c]pyran-7-yl]-n-methylmethanamine Chemical compound CNC[C@@H]1OCCC2=C1SC=C2 ABDDQTDRAHXHOC-QMMMGPOBSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
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- HCDMJFOHIXMBOV-UHFFFAOYSA-N 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one Chemical compound C=1C2=C3N(CC)C(=O)N(C=4C(=C(OC)C=C(OC)C=4F)F)CC3=CN=C2NC=1CN1CCOCC1 HCDMJFOHIXMBOV-UHFFFAOYSA-N 0.000 description 1
- BYHQTRFJOGIQAO-GOSISDBHSA-N 3-(4-bromophenyl)-8-[(2R)-2-hydroxypropyl]-1-[(3-methoxyphenyl)methyl]-1,3,8-triazaspiro[4.5]decan-2-one Chemical compound C[C@H](CN1CCC2(CC1)CN(C(=O)N2CC3=CC(=CC=C3)OC)C4=CC=C(C=C4)Br)O BYHQTRFJOGIQAO-GOSISDBHSA-N 0.000 description 1
- WNEODWDFDXWOLU-QHCPKHFHSA-N 3-[3-(hydroxymethyl)-4-[1-methyl-5-[[5-[(2s)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl]amino]-6-oxopyridin-3-yl]pyridin-2-yl]-7,7-dimethyl-1,2,6,8-tetrahydrocyclopenta[3,4]pyrrolo[3,5-b]pyrazin-4-one Chemical compound C([C@@H](N(CC1)C=2C=NC(NC=3C(N(C)C=C(C=3)C=3C(=C(N4C(C5=CC=6CC(C)(C)CC=6N5CC4)=O)N=CC=3)CO)=O)=CC=2)C)N1C1COC1 WNEODWDFDXWOLU-QHCPKHFHSA-N 0.000 description 1
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- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 239000002346 layers by function Substances 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 239000007773 negative electrode material Substances 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 125000005564 oxazolylene group Chemical group 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000005551 pyridylene group Chemical group 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000005576 pyrimidinylene group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 125000005557 thiazolylene group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 125000005730 thiophenylene group Chemical group 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000005559 triazolylene group Chemical group 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 238000001771 vacuum deposition Methods 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
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- 238000005406 washing Methods 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
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D405/14—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 three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/361—Polynuclear complexes, i.e. complexes comprising two or more metal centers
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- 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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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- 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
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
Definitions
- the present invention relates to a novel organic light emitting compound and an organic electroluminescent device using the same, and more particularly, a novel compound having excellent hole, electron injection and transporting ability, light emitting ability, etc.
- the present invention relates to an organic EL device having improved characteristics such as voltage and lifetime.
- the material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to its function.
- the light emitting layer forming material of the organic EL device may be classified into blue, green, and red light emitting materials according to light emission colors. In addition, yellow and orange light emitting materials are also used as light emitting materials to realize better natural colors.
- a host / dopant system may be used as the light emitting material in order to increase the light emission efficiency through increase in color purity and energy transfer.
- the dopant material may be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. The development of such phosphorescent materials can theoretically improve luminous efficiency up to 4 times compared to fluorescence, and thus, attention has been focused on phosphorescent dopants as well as phosphorescent host materials.
- NPB hole blocking layer
- BCP hole blocking layer
- Alq 3 hole blocking layer
- anthracene derivatives have been reported as fluorescent dopant / host materials in the light emitting material.
- phosphorescent materials having great advantages in terms of efficiency improvement among light emitting materials include metal complex compounds containing Ir such as Firpic, Ir (ppy) 3 , and (acac) Ir (btp) 2, such as blue, green, and red dopant materials. Is being used.
- CBP has shown excellent properties as a phosphorescent host material.
- the present invention can be applied to an organic electroluminescent device, and an object of the present invention is to provide a novel organic compound having excellent luminous ability.
- Another object of the present invention is to provide an organic electroluminescent device which exhibits a low driving voltage and high efficiency, including the novel organic compound.
- the present invention provides a compound represented by the following formula (1).
- L 1 and L 2 are the same as or different from each other, and each independently a single bond, or a C 6 to C 18 arylene group and a nuclear atom having 5 to 18 heteroarylene groups, and
- Ar 1 and Ar 2 are the same as or different from each other,
- Ar 1 is hydrogen, deuterium (D), halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 Cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, alkyloxy group of C 1 to C 40 , C 6 to C 60 Aryloxy group, C 1 to C 40 alkylsilyl group, C 6 to C 60 arylsilyl group, C 1 to C 40 alkyl boron group, C 6 to C 60 aryl boron group, C 6 to C 60 An aryl phosphine group, a C 6 -C 60 aryl phosphine oxide group and a C 6 -C 60 arylamine group,
- Ar 2 is hydrogen, deuterium (D), halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, an aryl group of C 6 to C 60 , an alkyloxy group of C 1 to C 40 , an aryloxy group of C 6 to C 60 , and an alkyl of C 1 to C 40 Silyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 arylphosphine group, C 6 ⁇ C 60 aryl It is selected from the group consisting of a phosphine oxide group and C 6 ⁇ C 60 arylamine group,
- the time period, alkylsilyl group, arylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and arylamine group are each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 of the alkynyl group, C 3 ⁇ C 40 cycloalkyl group, a nuclear atoms, 3 to 40 hetero cycloalkyl group, C 6 ⁇ C 60 the aryl group, the number of nuclear
- the present invention also provides an organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) at least one organic layer interposed between the anode and the cathode, wherein at least one of the at least one organic layer
- an organic electroluminescent device comprising a compound represented by the formula (1).
- the compound represented by Formula 1 of the present invention may be used as a material of the organic material layer of the organic electroluminescent device because of its excellent thermal stability and luminescence properties.
- an organic electroluminescent device having a lower driving voltage, higher efficiency, and longer life than a conventional host material can be manufactured. Improved full color display panels can also be manufactured.
- the present invention is based on carbazole (carbazole), and different moieties (eg, aryl group; nitrogen-containing heterocycle, etc.) are introduced at position 2 and N of the carbazole basic skeleton, respectively, It is characterized by forming an asymmetric structure represented.
- carbazole carbazole
- moieties eg, aryl group; nitrogen-containing heterocycle, etc.
- an electron donor group having a large electron donor such as phenyl, biphenyl, terphenyl, naphthyl group is substituted at the carbazole position 2, and a basic skeleton of carbazole (eg, N position)
- the electron-withdrawing group (EWG) having high electron absorption of a nitrogen-containing heterocycle e.g., pyridine group, pyrimidine group, triazine group, etc.
- the compound of Formula 1 may adjust HOMO and LUMO energy levels according to the type of substituents introduced into the basic skeleton, and may have a wide bandgap and may have high carrier transport properties.
- the compound of Formula 1 having EWG introduced into the basic skeleton has excellent carrier transport properties and excellent luminescence properties
- the compound of Formula 1 may also be used as an electron injection / transport layer material or a life improvement layer material in addition to the light emitting layer material of the organic EL device.
- the electron donor group (EDG) having a large electron donor such as an arylamine group, a carbazole group, a terphenyl group, a triphenylene group, and the like
- EDG electron donor group having a large electron donor such as an arylamine group, a carbazole group, a terphenyl group, a triphenylene group, and the like
- the injection and transport of holes may be smoothly performed. Therefore, in addition to the light emitting layer material, it can be usefully used as a hole injection / transport layer or light emitting auxiliary layer material.
- the compound represented by Chemical Formula 1 may improve light emission characteristics of the organic EL device, and improve hole injection / transportation capability, electron injection / transportation capability, luminous efficiency, driving voltage, and lifetime characteristics.
- the compound of formula 1 according to the present invention is an organic material layer material of an organic electroluminescent device, preferably a light emitting layer material (blue, green and / or red phosphorescent host material), an electron transport / injection layer material and a hole transport / injection layer Material, light emitting auxiliary layer material, life improving layer material, more preferably light emitting layer material, electron injection layer material, light emitting auxiliary layer material, and life improving layer material.
- the compound of Formula 1 has various substituents, particularly aryl groups and / or heteroaryl groups, introduced into the above-described basic skeleton to significantly increase the molecular weight of the compound, thereby improving the glass transition temperature (Tg), thereby making it a conventional light emitting material.
- Tg glass transition temperature
- 'CBP' 4,4-dicarbazolybiphenyl
- the compound represented by the formula (1) is Since it is also effective in suppressing crystallization, the organic electroluminescent device including the same may greatly improve performance and lifespan characteristics, and the full-color organic light emitting panel to which the organic electroluminescent device is applied may also maximize its performance.
- L 1 and L 2 are the same as or different from each other, and may be a linker of a conventional divalent group known in the art. In one example, it may be selected from the group consisting of a single bond, or is C 6 ⁇ C 18 arylene group and a nuclear atoms of 5 to 18 hetero arylene group for.
- L 1 and L 2 include a phenylene group, a biphenylene group, a naphthylene group, anthracenylene group, an indenylene group, a pyrantrenylene group, a carbazolylene group, a thiophenylene group, an indolylene group, and furinyl And an ethylene group, a quinolinyl group, a pyrrolyylene group, an imidazolylene group, an oxazolylene group, a thiazolylene group, a triazolylene group, a pyridinylene group, a pyrimidinylene group, and the like.
- L 1 is preferably a single bond, a phenylene group, or a biphenylene group.
- Ar 1 and Ar 2 may be the same as or different from each other, more specifically, Ar 1 is hydrogen, deuterium (D), halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 Alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 to C 60 aryl group, nuclear atom 5 to 60 hetero aryl group, C 1 ⁇ C 40 of the alkyloxy group, C 6 ⁇ C 60 of the aryloxy group, C 1 ⁇ C 40 alkyl silyl group, the group C 6 ⁇ C 60 aryl silyl, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C group 60 arylboronic of, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ C 60 aryl phosphine oxide group, and a C 6 ⁇ may be
- Ar 2 is hydrogen, deuterium (D), halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 Of a cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, an aryl group of C 6 to C 60 , an alkyloxy group of C 1 to C 40 , an aryloxy group of C 6 to C 60 , and a C 1 to C 40 group Alkylsilyl group, C 6 ⁇ C 60 Aryl silyl group, C 1 ⁇ C 40 Alkyl boron group, C 6 ⁇ C 60 Aryl boron group, C 6 ⁇ C 60 Aryl phosphine group, C 6 ⁇ C 60 It may be selected from the group consisting of aryl phosphine oxide group and C 6 ⁇ C 60 arylamine group.
- Ar 1 and Ar 2 are different from each other, Ar 1 is a heteroaryl group having 5 to 19 nuclear atoms, Ar 2 is preferably an C 6 ⁇ C 18 aryl group. Specifically Ar 2 may be selected from the group consisting of phenyl, biphenyl, terphenyl, naphthyl, and triphenylene.
- the aryl group and heteroaryl group of Ar 1 and Ar 2 are each independently substituted or unsubstituted with one or more substituents selected from the group consisting of C 6 ⁇ C 60 aryl group and a heteroaryl group of 5 to 60 nuclear atoms Can be.
- the time period, alkylsilyl group, arylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and arylamine group are each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 of the alkynyl group, C 3 ⁇ C 40 cycloalkyl group, a nuclear atoms, 3 to 40 hetero cycloalkyl group, C 6 ⁇ C 60 the aryl group, the number of nuclear
- Ar 1 may be a substituent represented by the following Chemical Formula 2.
- Z 1 to Z 5 are the same as or different from each other, and each independently N or C (R 1 ), but at least one of Z 1 to Z 5 is preferably N.
- a plurality of R 1 may be the same or different and are each independently hydrogen, deuterium (D), a halogen, a cyano group, a nitro group, an alkyl group of C 1 ⁇ C 40, C 2 ⁇ C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 to C 60 aryl group, nuclear atom 5 to 60 Heteroaryl group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C group 60 arylboronic of, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ C aryl phosphine oxide 60 group and
- R 1 is preferably selected from the group consisting of hydrogen, C 1 ⁇ C 40 alkyl group, C 6 ⁇ C 40 aryl group, and a heteroaryl group of 5 to 40 nuclear atoms.
- the arylphosphine group, the arylphosphine oxide group and the arylamine group are each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 Alkynyl group of ⁇ C 40 , cycloalkyl group of C 3 ⁇ C 40 , heterocycloalkyl group of 3 to 40 nuclear atoms, aryl group of C 6 ⁇ C 60 , heteroaryl group of 5 to 60 nuclear atoms,
- Substituents represented by the formula (2) may be more embodied in any one of the substituent group consisting of the formula A-1 to A-15.
- R 1 is as defined in Formula 2 above,
- n is an integer of 0 to 4, when n is 0, it means that hydrogen is not substituted with a substituent R 2 , when n is an integer of 1 to 4, R 2 is deuterium, halogen, cyano group, nitro C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 Aryl group of ⁇ C 40 , heteroaryl group of 5 to 40 nuclear atoms, aryloxy group of C 6 ⁇ C 40 60 C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 40 arylamine group, C 1 ⁇ C 40 alkyl silyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 40 aryl boron group, C 6 ⁇ C 40 aryl phosphine group, C 6 ⁇ aryl phosphine oxide of
- Alkyl group of the R 2 an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group,
- the arylphosphine group, the arylphosphine oxide group and the arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alky Neyl group, C 6 ⁇ C 40 aryl group, C 5 ⁇ C 40 heteroaryl group, C 6 ⁇ C 40 aryloxy group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 40 arylamine group, an aryl
- Ar 1 may be a substituent represented by the following Chemical Formula 3.
- Z is the same as or different from each other, and each independently N or C (R 3 ), but preferably at least one of the plurality of Z is N.
- R 3 when the R 3 is plural, plural R 3 may be the same or different, each independently represent hydrogen, deuterium (D), a halogen, a cyano group, a nitro group, an alkyl group of C 1 ⁇ C 40, C 2 ⁇ C 40 Alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 to C 60 aryl group, nuclear atom 5 to 60 hetero aryl group, C 1 ⁇ C 40 of the alkyloxy group, C 6 ⁇ C 60 of the aryloxy group, C 1 ⁇ C 40 alkyl silyl group, the group C 6 ⁇ C 60 aryl silyl, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C group 60 arylboronic of, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ C 60 aryl phosphine oxide group, and
- X may be O or S.
- R 4 to R 5 are the same or different and are each independently hydrogen, deuterium (D), a halogen, a cyano group, a nitro group, C 1 ⁇ alkenyl group of the C 40 alkyl group, C 2 ⁇ C 40 of, C 2 Alkynyl group of ⁇ C 40 , cycloalkyl group of C 3 ⁇ C 40 , heterocycloalkyl group of 3 to 40 nuclear atoms, aryl group of C 6 ⁇ C 60 , heteroaryl group of 5 to 60 nuclear atoms, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ an aryl boronic of C 60, C 6 ⁇ C 60 aryl phosphine group, a group of C 6 ⁇ C 60 aryl phosphin
- R 4 is a C 6 ⁇ C 18 aryl group
- R 5 is hydrogen, C 1 ⁇ C 40 alkyl group, C 6 ⁇ C 40 aryl group, and a nuclear atom of 5 to 40 hetero It is preferably selected from the group consisting of aryl groups.
- R 4 may be selected from the group consisting of phenyl, biphenyl, terphenyl, naphthyl, and triphenylene.
- n is an integer of 0 to 7, and when n is 2 or more, a plurality of R 5 may be the same or different from each other.
- n 0, it means that hydrogen is not substituted with a substituent R 5 , and when n is 1 to 7, R 5 may independently have the aforementioned substituents except for hydrogen.
- Z and R 4 are each as defined in Chemical Formula 3 described above.
- the compound represented by the formula (1) of the present invention described above may be more specifically represented by the compound represented by any one of formulas 1-1 to 7-23 illustrated below.
- the compound represented by the formula (1) of the present invention is not limited by those illustrated below.
- Alkyl in the present invention means a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl and the like.
- alkenyl refers to a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon double bond. Examples thereof include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like.
- alkynyl refers to a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon triple bond. Examples thereof include, but are not limited to, ethynyl, 2-propynyl, and the like.
- Aryl in the present invention means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 40 carbon atoms combined with a single ring or two or more rings.
- a form in which two or more rings are attached to each other (pendant) or condensed may also be included.
- Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.
- Heteroaryl as used herein means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclear atoms. At least one carbon in the ring, preferably 1 to 3 carbons, is substituted with a heteroatom such as N, O, S or Se.
- a form in which two or more rings are pendant or condensed with each other may be included, and may also include a form in which the two or more rings are condensed with an aryl group.
- heteroaryl examples include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolinzinyl, indolyl ( polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, carbazolyl and 2-furanyl, N-imidazolyl, 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.
- 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolinzinyl, indolyl ( polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, carb
- aryloxy is a monovalent substituent represented by RO-, wherein R means aryl having 5 to 40 carbon atoms.
- R means aryl having 5 to 40 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.
- alkyloxy is a monovalent substituent represented by R'O-, wherein R 'means an alkyl having 1 to 40 carbon atoms, linear, branched or cyclic structure It may include.
- alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.
- Arylamine in the present invention means an amine substituted with aryl having 6 to 40 carbon atoms.
- Cycloalkyl as used herein means monovalent substituents derived from monocyclic or polycyclic non-aromatic hydrocarbons having 3 to 40 carbon atoms. Examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
- heterocycloalkyl monovalent substituents derived from non-aromatic hydrocarbons having 3 to 40 nuclear atoms, wherein at least one carbon in the ring, preferably 1 to 3 carbons, is N, O, S Or a hetero atom such as Se.
- heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.
- alkylsilyl means silyl substituted with alkyl having 1 to 40 carbon atoms
- arylsilyl means silyl substituted with aryl having 5 to 40 carbon atoms
- condensed ring means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.
- organic electroluminescent device comprising the compound represented by the formula (1) according to the present invention.
- the organic electroluminescent device includes an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode, and at least one of the one or more organic material layers.
- a compound represented by the formula (1) includes a compound represented by the formula (1).
- the compound may be used alone, or two or more may be used in combination.
- the one or more organic material layers may be any one or more of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport layer and an electron injection layer, wherein at least one organic material layer may include a compound represented by Formula 1 have.
- the organic material layer including the compound of Formula 1 is preferably a light emitting layer, an electron transport layer, a hole transport layer.
- the light emitting layer of the organic electroluminescent device of the present invention may include a host material, and may include the compound of Formula 1 as the host material.
- the light emitting layer of the organic electroluminescent device of the present invention may include a compound other than the compound of Formula 1 as a host.
- the compound represented by Chemical Formula 1 is included as a light emitting layer material of the organic electroluminescent device, preferably a blue, green, or red phosphorescent host material, the binding force between the holes and the electrons in the light emitting layer increases, so that the efficiency of the organic electroluminescent device (Luminescence efficiency and power efficiency), lifetime, brightness and driving voltage can be improved.
- the compound represented by Chemical Formula 1 is preferably included in the organic electroluminescent device as a green and / or red phosphorescent host, fluorescent host, or dopant material.
- the compound represented by Formula 1 of the present invention is preferably a phosphorescent host, a fluorescent host or a dopant material of the light emitting layer, and more preferably a phosphorescent host of the light emitting layer.
- the structure of the organic EL device of the present invention is not particularly limited, but may be a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport layer, and a cathode are sequentially stacked.
- the hole injection layer, the hole transport layer, the light emitting auxiliary layer, the light emitting layer, the electron transport layer and the electron injection layer may include a compound represented by the formula (1), preferably a hole transport layer, electron blocking layer, light emission
- the auxiliary layer may include a compound represented by Chemical Formula 1. Meanwhile, an electron injection layer may be further stacked on the electron transport layer.
- the organic electroluminescent device of the present invention may have a structure in which an insulating layer or an adhesive layer is inserted between an electrode and an organic material layer interface.
- the organic electroluminescent device of the present invention can be manufactured by forming an organic material layer and an electrode by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound represented by Chemical Formula 1.
- the organic material layer may be formed by a vacuum deposition method or a solution coating method.
- the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.
- the substrate used in the manufacture of the organic EL device of the present invention is not particularly limited, but silicon wafers, quartz, glass plates, metal plates, plastic films, sheets, and the like may be used.
- examples of the anode material include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole or polyaniline; And carbon black, but are not limited thereto.
- metals such as vanadium, chromium, copper, zinc and gold or alloys thereof.
- Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb
- Conductive polymers such as polythiophene, poly (3-methylthiophene
- the negative electrode material may be a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or an alloy thereof; And multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like, but are not limited thereto.
- the hole injection layer, the hole transport layer, the electron injection layer and the electron transport layer is not particularly limited, and conventional materials known in the art may be used.
- a glass substrate coated with ITO Indium tin oxide having a thickness of 1500 ⁇ was washed with distilled water ultrasonic waves. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc. is dried and transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech). The substrate was transferred to.
- ITO Indium tin oxide
- UV OZONE cleaner Power sonic 405, Hwasin Tech
- a green organic EL device was manufactured in the same manner as in Example 1, except that CBP was used instead of Compound 1-1 as a light emitting host material when forming the emission layer.
- Example 1 1-1 6.64 516 42.2 Example 2 1-2 6.35 517 47.4 Example 3 1-4 6.62 518 49.2 Example 4 1-7 6.53 516 44.8 Example 5 1-8 6.36 517 43.1 Example 6 1-10 6.88 516 43.6 Example 7 1-12 6.44 516 47.4 Example 8 1-14 6.62 516 43.4 Example 9 1-17 6.46 517 49.2 Example 10 1-19 6.39 516 47.4 Example 11 1-20 6.74 516 47.6 Example 12 1-22 6.81 518 43.2 Example 13 2-1 6.38 516 47.4 Example 14 2-2 6.54 518 44.1 Example 15 2-4 6.67 517 42.4 Example 16 2-7 6.32 517 46.7 Example 17 2-8 6.55 516 44.8 Example 18 2-10 6.83 518 43.5 Example 19 2-12 6.16 516 48.1 Example 20 2-14 6.24 516 49.6 Example 21 2-17 6.26 517 49.9 Example 22 2-19 6.18 518 47.4
- the green organic EL device of Examples 1 to 84 using the compound (1-1 to 7-23) according to the present invention as a light emitting layer of the green organic EL device is a comparative example using conventional CBP. Compared with the green organic EL device of 1, it was found to exhibit better performance in terms of efficiency and driving voltage.
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Abstract
The present invention relates to: a novel compound having an excellent light-emitting ability; and an organic electroluminescent element comprising the same in one or more organic material layers, thereby having improved characteristics such as light-emitting efficiency, driving voltage, and lifespan.
Description
본 발명은 신규한 유기 발광 화합물 및 이를 이용한 유기 전계 발광 소자에 관한 것으로, 보다 상세하게는 정공, 전자 주입 및 수송능, 발광능 등이 우수한 신규 화합물 및 이를 하나 이상의 유기물층에 포함함으로써 발광효율, 구동 전압, 수명 등의 특성이 향상된 유기 전계 발광 소자에 관한 것이다.The present invention relates to a novel organic light emitting compound and an organic electroluminescent device using the same, and more particularly, a novel compound having excellent hole, electron injection and transporting ability, light emitting ability, etc. The present invention relates to an organic EL device having improved characteristics such as voltage and lifetime.
1950년대 Bernanose의 유기 박막 발광 관측을 시점으로 1965년 안트라센 단결정을 이용한 청색 전기발광으로 이어진 유기 전계 발광(electroluminescent, EL) 소자(이하, 간단히 '유기 EL 소자'로 칭함)에 대한 연구는 1987년 탕(Tang)에 의하여 정공층과 발광층의 기능층으로 나눈 적층구조의 유기 EL 소자가 제시되었다. 이후 고효율, 고수명의 유기 EL 소자를 만들기 위하여, 소자 내 각각의 특징적인 유기물 층을 도입하는 형태로 발전하여 왔으며, 이에 사용되는 특화된 물질의 개발로 이어졌다. The study of organic electroluminescent (EL) devices (hereinafter referred to simply as 'organic EL devices') led to blue electroluminescence using anthracene monocrystals in 1965, based on Bernanose's observation of organic thin film emission in the 1950s. By (Tang), an organic EL device having a laminated structure divided into a functional layer of a hole layer and a light emitting layer has been proposed. Since then, in order to make high-efficiency, high-life organic EL devices, the development has been made in the form of introducing each characteristic organic material layer in the device, leading to the development of specialized materials used therein.
유기 전계 발광 소자는 두 전극 사이에 전압을 걸어 주면 양극에서는 정공이 주입되고, 음극에서는 전자가 유기물층으로 주입된다. 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 바닥상태로 떨어질 때 빛이 나게 된다. 이때 유기물층으로 사용되는 물질은 그 기능에 따라, 발광 물질, 정공 주입 물질, 정공 수송 물질, 전자 수송 물질, 전자 주입 물질 등으로 분류될 수 있다. In the organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected from the anode, and electrons are injected into the organic material layer from the cathode. When the injected holes and electrons meet, excitons are formed, and when the excitons fall to the ground, they shine. In this case, the material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to its function.
유기 EL 소자의 발광층 형성재료는 발광색에 따라 청색, 녹색, 적색 발광 재료로 구분될 수 있다. 그밖에, 보다 나은 천연색을 구현하기 위한 발광재료로 노란색 및 주황색 발광재료도 사용된다. 또한, 색순도의 증가와 에너지 전이를 통한 발광 효율을 증가시키기 위하여, 발광 재료로서 호스트/도펀트 계를 사용할 수 있다. 도판트 물질은 유기 물질을 사용하는 형광 도판트와 Ir, Pt 등의 중원자(heavy atoms)가 포함된 금속 착체 화합물을 사용하는 인광 도판트로 나눌 수 있다. 이러한 인광 재료의 개발은 이론적으로 형광에 비해 4배까지의 발광 효율을 향상시킬 수 있어 인광 도판트 뿐만 아니라 인광 호스트 재료들에 대해 관심이 집중되고 있다. The light emitting layer forming material of the organic EL device may be classified into blue, green, and red light emitting materials according to light emission colors. In addition, yellow and orange light emitting materials are also used as light emitting materials to realize better natural colors. In addition, a host / dopant system may be used as the light emitting material in order to increase the light emission efficiency through increase in color purity and energy transfer. The dopant material may be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. The development of such phosphorescent materials can theoretically improve luminous efficiency up to 4 times compared to fluorescence, and thus, attention has been focused on phosphorescent dopants as well as phosphorescent host materials.
현재까지 정공 주입층, 정공 수송층. 정공 차단층, 전자 수송층으로는, 하기 화학식으로 표현된 NPB, BCP, Alq3 등이 널리 알려져 있고, 발광 재료는 안트라센 유도체들이 형광 도판트/호스트 재료로서 보고되고 있다. 특히 발광재료 중 효율 향상 측면에서 큰 장점을 가지고 있는 인광 재료로서는 Firpic, Ir(ppy)3, (acac)Ir(btp)2 등과 같은 Ir을 포함하는 금속 착체 화합물이 청색, 녹색, 적색 도판트 재료로 사용되고 있다. 현재까지는 CBP가 인광 호스트 재료로 우수한 특성을 나타내고 있다. Hole injection layer, hole transport layer to date. As the hole blocking layer and the electron transporting layer, NPB, BCP, Alq 3 and the like represented by the following formulas are widely known, and anthracene derivatives have been reported as fluorescent dopant / host materials in the light emitting material. Particularly, phosphorescent materials having great advantages in terms of efficiency improvement among light emitting materials include metal complex compounds containing Ir such as Firpic, Ir (ppy) 3 , and (acac) Ir (btp) 2, such as blue, green, and red dopant materials. Is being used. To date, CBP has shown excellent properties as a phosphorescent host material.
그러나 기존의 재료들은 발광 특성 측면에서는 유리한 면이 있으나, 유리전이온도가 낮고 열적 안정성이 매우 좋지 않아 유기 EL 소자에서의 수명 측면에서 만족할만한 수준이 되지 못하고 있다. However, existing materials have advantages in terms of luminescence properties, but the glass transition temperature is low and the thermal stability is very poor, and thus the materials are not satisfactory in terms of lifespan in organic EL devices.
본 발명은 유기 전계 발광 소자에 적용할 수 있으며, 발광능이 우수한 신규 유기 화합물을 제공하는 것을 목적으로 한다.The present invention can be applied to an organic electroluminescent device, and an object of the present invention is to provide a novel organic compound having excellent luminous ability.
또한, 본 발명은 상기 신규 유기 화합물을 포함하여 낮은 구동전압과 높은 효율을 나타내는 유기 전계 발광 소자를 제공하는 것을 또 다른 목적으로 한다.In addition, another object of the present invention is to provide an organic electroluminescent device which exhibits a low driving voltage and high efficiency, including the novel organic compound.
전술한 목적을 달성하기 위해, 본 발명은 하기 화학식 1로 표시되는 화합물을 제공한다.In order to achieve the above object, the present invention provides a compound represented by the following formula (1).
상기 화학식 1에서,In Chemical Formula 1,
L1 및 L2는 서로 동일하거나 상이하며, 각각 독립적으로 단일결합이거나, 또는 C6~C18의 아릴렌기 및 핵원자수 5 내지 18개의 헤테로아릴렌기로 이루어진 군에서 선택되고,L 1 and L 2 are the same as or different from each other, and each independently a single bond, or a C 6 to C 18 arylene group and a nuclear atom having 5 to 18 heteroarylene groups, and
Ar1과 Ar2는 서로 동일하거나 또는 상이하며, Ar 1 and Ar 2 are the same as or different from each other,
Ar1는 수소, 중수소(D), 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되고,Ar 1 is hydrogen, deuterium (D), halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 Cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, alkyloxy group of C 1 to C 40 , C 6 to C 60 Aryloxy group, C 1 to C 40 alkylsilyl group, C 6 to C 60 arylsilyl group, C 1 to C 40 alkyl boron group, C 6 to C 60 aryl boron group, C 6 to C 60 An aryl phosphine group, a C 6 -C 60 aryl phosphine oxide group and a C 6 -C 60 arylamine group,
Ar2는 수소, 중수소(D), 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되고,Ar 2 is hydrogen, deuterium (D), halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, an aryl group of C 6 to C 60 , an alkyloxy group of C 1 to C 40 , an aryloxy group of C 6 to C 60 , and an alkyl of C 1 to C 40 Silyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 arylphosphine group, C 6 ~ C 60 aryl It is selected from the group consisting of a phosphine oxide group and C 6 ~ C 60 arylamine group,
상기 L1 및 L2의 아릴렌기 및 헤테로아릴렌기와, 상기 Ar1 및 Ar2의 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기 및 아릴아민기는 각각 독립적으로 수소, 중수소(D), 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환될 수 있으며, 이때 상기 치환기가 복수인 경우, 이들은 서로 동일하거나 상이할 수 있다.The arylene group and heteroarylene group of L 1 and L 2 , the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryl jade of Ar 1 and Ar 2 The time period, alkylsilyl group, arylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and arylamine group are each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 of the alkynyl group, C 3 ~ C 40 cycloalkyl group, a nuclear atoms, 3 to 40 hetero cycloalkyl group, C 6 ~ C 60 the aryl group, the number of nuclear atoms aryl of from 5 to 60 heteroaryl group, a C 1 ~ C 40 alkyloxy group of, C 6 ~ aryloxy C 60, C 1 ~ C 40 alkyl silyl group, C 6 ~ C 60 aryl silyl group, C 1 ~ C 40 group of an alkyl boron, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 aryl phosphine oxide group, and a C 6 ~ of C 60 It may be substituted with 1 substituent selected from the group consisting of two or more amine groups, and the reel, wherein when the substituent is plural, they may be the same or different from each other.
또한, 본 발명은 (i) 양극, (ii) 음극, 및 (iii) 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하는 유기 전계 발광 소자로서, 상기 1층 이상의 유기물층 중 적어도 하나는 상기 화학식 1로 표시되는 화합물을 포함하는 것을 특징으로 하는 유기 전계 발광 소자를 제공한다. The present invention also provides an organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) at least one organic layer interposed between the anode and the cathode, wherein at least one of the at least one organic layer One provides an organic electroluminescent device comprising a compound represented by the formula (1).
본 발명의 화학식 1로 표시되는 화합물은 열적 안정성 및 발광 특성이 우수하기 때문에 유기 전계 발광 소자의 유기물층의 재료로 사용될 수 있다.The compound represented by Formula 1 of the present invention may be used as a material of the organic material layer of the organic electroluminescent device because of its excellent thermal stability and luminescence properties.
특히, 본 발명의 화학식 1로 표시되는 화합물을 인광 호스트 재료로 사용할 경우, 종래의 호스트 재료에 비해 낮은 구동전압, 높은 효율 및 장수명을 갖는 유기 전계 발광 소자를 제조할 수 있고, 나아가 성능 및 수명이 향상된 풀 칼라 디스플레이 패널도 제조할 수 있다.In particular, when the compound represented by Formula 1 of the present invention is used as a phosphorescent host material, an organic electroluminescent device having a lower driving voltage, higher efficiency, and longer life than a conventional host material can be manufactured. Improved full color display panels can also be manufactured.
이하, 본 발명을 상세히 설명한다.Hereinafter, the present invention will be described in detail.
<신규 유기 화합물><New organic compound>
본 발명은 카바졸(carbazole)을 기본 골격으로 하며, 상기 카바졸 기본 골격의 2번 위치와 N 위치에 서로 다른 모이어티(예, 아릴기; 질소 함유 헤테로환 등)가 각각 도입되어 화학식 1로 표시되는 비대칭 구조(asymmetric structure)를 형성하는 것을 특징으로 한다. The present invention is based on carbazole (carbazole), and different moieties (eg, aryl group; nitrogen-containing heterocycle, etc.) are introduced at position 2 and N of the carbazole basic skeleton, respectively, It is characterized by forming an asymmetric structure represented.
상기 화학식 1의 화합물은, 카바졸 2번 위치에 페닐, 바이페닐, 터트페닐, 나프틸기 등의 전자공여성이 큰 전자주게기(EDG)가 치환되고, 카바졸의 기본 골격(예, N 위치)에 질소-함유 헤테로환(예컨대, 피리딘기, 피리미딘기, 트리아진기 등)의 전자 흡수성이 큰 전자 끌개기(EWG)가 결합되어 분자 전체가 바이폴라(bipolar) 특성을 갖기 때문에, 정공과 전자의 결합력을 높일 수 있다. 또한 상기 화학식 1의 화합물은 상기 기본 골격에 도입되는 치환기의 종류에 따라 HOMO 및 LUMO 에너지 레벨을 조절할 수 있어, 넓은 밴드갭을 가질 수 있고 높은 캐리어 수송성을 가질 수 있다.In the compound of Formula 1, an electron donor group (EDG) having a large electron donor such as phenyl, biphenyl, terphenyl, naphthyl group is substituted at the carbazole position 2, and a basic skeleton of carbazole (eg, N position) The electron-withdrawing group (EWG) having high electron absorption of a nitrogen-containing heterocycle (e.g., pyridine group, pyrimidine group, triazine group, etc.) is bonded to the whole molecule, so that the entire molecule has a bipolar characteristic. It can increase the bonding force. In addition, the compound of Formula 1 may adjust HOMO and LUMO energy levels according to the type of substituents introduced into the basic skeleton, and may have a wide bandgap and may have high carrier transport properties.
구체적으로, 상기 기본 골격에 EWG가 도입된 상기 화학식 1의 화합물은 우수한 캐리어 수송성 및 발광 특성이 우수하기 때문에, 유기 전계 발광 소자의 발광층 재료 이외에, 전자주입/수송층 재료, 또는 수명 개선층 재료로도 사용될 수 있다. 또한, 상기 화학식 1의 기본 골격에 아릴아민기, 카바졸기, 터페닐기, 트리페닐렌기 등과 같이 전자 공여성이 큰 전자 주게기(EDG)가 결합될 경우, 정공의 주입 및 수송이 원활하게 이루어지기 때문에, 발광층 재료 이외에, 정공주입/수송층 또는 발광 보조층 재료로도 유용하게 사용될 수 있다.Specifically, since the compound of Formula 1 having EWG introduced into the basic skeleton has excellent carrier transport properties and excellent luminescence properties, the compound of Formula 1 may also be used as an electron injection / transport layer material or a life improvement layer material in addition to the light emitting layer material of the organic EL device. Can be used. In addition, when the electron donor group (EDG) having a large electron donor such as an arylamine group, a carbazole group, a terphenyl group, a triphenylene group, and the like are combined with the basic skeleton of Formula 1, the injection and transport of holes may be smoothly performed. Therefore, in addition to the light emitting layer material, it can be usefully used as a hole injection / transport layer or light emitting auxiliary layer material.
상기와 같이, 화학식 1로 표시되는 화합물은 유기 전계 발광 소자의 발광 특성을 향상시킴과 동시에, 정공 주입/수송 능력, 전자 주입/수송 능력, 발광 효율, 구동 전압, 수명 특성 등을 향상시킬 수 있다. 따라서, 본 발명에 따른 화학식 1의 화합물은 유기 전계 발광 소자의 유기물층 재료, 바람직하게는 발광층 재료(청색, 녹색 및/또는 적색의 인광 호스트 재료), 전자 수송/주입층 재료 및 정공 수송/주입층 재료, 발광보조층 재료, 수명개선층 재료, 더 바람직하게는 발광층 재료, 전자 주입층 재료, 발광보조층 재료, 수명 개선층 재료로 사용될 수 있다.As described above, the compound represented by Chemical Formula 1 may improve light emission characteristics of the organic EL device, and improve hole injection / transportation capability, electron injection / transportation capability, luminous efficiency, driving voltage, and lifetime characteristics. . Accordingly, the compound of formula 1 according to the present invention is an organic material layer material of an organic electroluminescent device, preferably a light emitting layer material (blue, green and / or red phosphorescent host material), an electron transport / injection layer material and a hole transport / injection layer Material, light emitting auxiliary layer material, life improving layer material, more preferably light emitting layer material, electron injection layer material, light emitting auxiliary layer material, and life improving layer material.
나아가, 상기 화학식 1의 화합물은 전술한 기본 골격에 다양한 치환체, 특히 아릴기 및/또는 헤테로아릴기가 도입되어 화합물의 분자량이 유의적으로 증대됨으로써, 유리 전이온도(Tg)가 향상되어 종래의 발광 재료(예를 들어, 4,4-dicarbazolybiphenyl (이하, 'CBP'라 함)보다 높은 열적 안정성을 가질 뿐만 아니라 캐리어 수송능, 발광능 등이 우수하다. 또한, 상기 화학식 1로 표시되는 화합물은 유기물층의 결정화 억제에도 효과가 있으므로, 이를 포함하는 유기 전계 발광 소자는 성능 및 수명 특성이 크게 향상될 수 있고, 이러한 유기 전계 발광 소자가 적용된 풀 칼라 유기 발광 패널도 성능이 극대화될 수 있다.Furthermore, the compound of Formula 1 has various substituents, particularly aryl groups and / or heteroaryl groups, introduced into the above-described basic skeleton to significantly increase the molecular weight of the compound, thereby improving the glass transition temperature (Tg), thereby making it a conventional light emitting material. (For example, 4,4-dicarbazolybiphenyl (hereinafter referred to as 'CBP') not only has a high thermal stability, but also excellent carrier transport ability, luminous ability, etc. In addition, the compound represented by the formula (1) is Since it is also effective in suppressing crystallization, the organic electroluminescent device including the same may greatly improve performance and lifespan characteristics, and the full-color organic light emitting panel to which the organic electroluminescent device is applied may also maximize its performance.
본 발명에 따라 화학식 1로 표시되는 화합물에서, L1 및 L2는 서로 동일하거나 상이하며, 당 분야에 알려진 통상적인 통상적인 2가(divalent) 그룹의 연결기(Linker)일 수 있다. 일례로, 단일결합이거나, 또는 C6~C18의 아릴렌기 및 핵원자수 5 내지 18의 헤테로아릴렌기로 이루어진 군에서 선택될 수 있다. In the compound represented by Formula 1 according to the present invention, L 1 and L 2 are the same as or different from each other, and may be a linker of a conventional divalent group known in the art. In one example, it may be selected from the group consisting of a single bond, or is C 6 ~ C 18 arylene group and a nuclear atoms of 5 to 18 hetero arylene group for.
상기 L1과 L2의 보다 구체적인 예로는 페닐렌기, 비페닐렌기, 나프틸렌기, 안트라세닐렌기, 인데닐렌기, 피란트레닐렌기, 카르바졸릴렌기, 티오페닐렌기, 인돌일렌기, 푸리닐렌기, 퀴놀리닐렌기, 피롤일렌기, 이미다졸릴렌기, 옥사졸릴렌기, 티아졸릴렌기, 트리아졸릴렌기, 피리디닐렌기, 피리미디닐렌기 등이 있다. 상기 화학식 1에서, L1은 단일결합이거나, 페닐렌기, 또는 비페닐렌기인 것이 바람직하다.More specific examples of L 1 and L 2 include a phenylene group, a biphenylene group, a naphthylene group, anthracenylene group, an indenylene group, a pyrantrenylene group, a carbazolylene group, a thiophenylene group, an indolylene group, and furinyl And an ethylene group, a quinolinyl group, a pyrrolyylene group, an imidazolylene group, an oxazolylene group, a thiazolylene group, a triazolylene group, a pyridinylene group, a pyrimidinylene group, and the like. In Formula 1, L 1 is preferably a single bond, a phenylene group, or a biphenylene group.
Ar1과 Ar2는 서로 동일하거나 또는 상이할 수 있으며, 보다 구체적으로, Ar1는 수소, 중수소(D), 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택될 수 있다. Ar 1 and Ar 2 may be the same as or different from each other, more specifically, Ar 1 is hydrogen, deuterium (D), halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 Alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 to C 60 aryl group, nuclear atom 5 to 60 hetero aryl group, C 1 ~ C 40 of the alkyloxy group, C 6 ~ C 60 of the aryloxy group, C 1 ~ C 40 alkyl silyl group, the group C 6 ~ C 60 aryl silyl, C 1 ~ C 40 alkyl boron group, C 6 ~ C group 60 arylboronic of, C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 aryl phosphine oxide group, and a C 6 ~ may be selected from the group consisting of an aryl amine of the C 60 have.
또한 Ar2는 수소, 중수소(D), 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택될 수 있다. In addition, Ar 2 is hydrogen, deuterium (D), halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 Of a cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, an aryl group of C 6 to C 60 , an alkyloxy group of C 1 to C 40 , an aryloxy group of C 6 to C 60 , and a C 1 to C 40 group Alkylsilyl group, C 6 ~ C 60 Aryl silyl group, C 1 ~ C 40 Alkyl boron group, C 6 ~ C 60 Aryl boron group, C 6 ~ C 60 Aryl phosphine group, C 6 ~ C 60 It may be selected from the group consisting of aryl phosphine oxide group and C 6 ~ C 60 arylamine group.
본 발명에서, Ar1과 Ar2는 서로 상이하며, Ar1은 핵원자수 5 내지 19의 헤테로아릴기이며, Ar2는 C6~C18의 아릴기인 것이 바람직하다. 구체적으로 Ar2는 페닐, 비페닐, 터페닐, 나프틸, 및 트리페닐렌으로 이루어진 군에서 선택될 수 있다.In the present invention, Ar 1 and Ar 2 are different from each other, Ar 1 is a heteroaryl group having 5 to 19 nuclear atoms, Ar 2 is preferably an C 6 ~ C 18 aryl group. Specifically Ar 2 may be selected from the group consisting of phenyl, biphenyl, terphenyl, naphthyl, and triphenylene.
이때 상기 Ar1과 Ar2의 아릴기와 헤테로아릴기는 각각 독립적으로 C6~C60의 아릴기 및 핵원자수 5 내지 60의 헤테로아릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 또는 비치환될 수 있다. At this time, the aryl group and heteroaryl group of Ar 1 and Ar 2 are each independently substituted or unsubstituted with one or more substituents selected from the group consisting of C 6 ~ C 60 aryl group and a heteroaryl group of 5 to 60 nuclear atoms Can be.
상기 L1 및 L2의 아릴렌기 및 헤테로아릴렌기와, 상기 Ar1 및 Ar2의 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기 및 아릴아민기는 각각 독립적으로 수소, 중수소(D), 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환될 수 있으며, 이때 상기 치환기가 복수인 경우, 이들은 서로 동일하거나 상이할 수 있다.The arylene group and heteroarylene group of L 1 and L 2 , the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryl jade of Ar 1 and Ar 2 The time period, alkylsilyl group, arylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and arylamine group are each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 of the alkynyl group, C 3 ~ C 40 cycloalkyl group, a nuclear atoms, 3 to 40 hetero cycloalkyl group, C 6 ~ C 60 the aryl group, the number of nuclear atoms aryl of from 5 to 60 heteroaryl group, a C 1 ~ C 40 alkyloxy group of, C 6 ~ aryloxy C 60, C 1 ~ C 40 alkyl silyl group, C 6 ~ C 60 aryl silyl group, C 1 ~ C 40 group of an alkyl boron, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 aryl phosphine oxide group, and a C 6 ~ of C 60 It may be substituted with 1 substituent selected from the group consisting of two or more amine groups, and the reel, wherein when the substituent is plural, they may be the same or different from each other.
한편 본 발명에 따른 화학식 1로 표시되는 화합물에서, Ar1은 하기 화학식 2로 표시되는 치환체일 수 있다. Meanwhile, in the compound represented by Chemical Formula 1 according to the present invention, Ar 1 may be a substituent represented by the following Chemical Formula 2.
상기 화학식 2에서,In Chemical Formula 2,
*는 상기 화학식 1에 결합되는 부분을 의미하고,* Means a moiety bonded to Formula 1,
Z1 내지 Z5는 서로 동일하거나 상이하며, 각각 독립적으로 N 또는 C(R1)이고, 다만 Z1 내지 Z5 중 적어도 하나는 N인 것이 바람직하다. Z 1 to Z 5 are the same as or different from each other, and each independently N or C (R 1 ), but at least one of Z 1 to Z 5 is preferably N.
또한 R1이 복수인 경우, 복수의 R1은 서로 동일하거나 또는 상이하며, 각각 독립적으로 수소, 중수소(D), 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 또는 인접하는 기(예컨대 L1, 인접하는 다른 R1)과 결합하여 축합 고리를 형성할 수 있다. In addition, when the R 1 is plural, a plurality of R 1 may be the same or different and are each independently hydrogen, deuterium (D), a halogen, a cyano group, a nitro group, an alkyl group of C 1 ~ C 40, C 2 ~ C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 to C 60 aryl group, nuclear atom 5 to 60 Heteroaryl group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C group 60 arylboronic of, C 6 ~ C 60 aryl phosphine group, C 6 ~ C aryl phosphine oxide 60 group and a C 6 ~ selected from the group consisting of an aryl amine of the C 60 or , Or may be combined with adjacent groups (eg L 1 , other adjacent R 1 ) to form a condensed ring.
이때 R1은 수소, C1~C40의 알킬기, C6~C40의 아릴기, 및 핵원자수 5 내지 40의 헤테로아릴기로 구성된 군에서 선택되는 것이 바람직하다. At this time, R 1 is preferably selected from the group consisting of hydrogen, C 1 ~ C 40 alkyl group, C 6 ~ C 40 aryl group, and a heteroaryl group of 5 to 40 nuclear atoms.
상기 R1의 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기 및 아릴아민기는 각각 독립적으로 수소, 중수소(D), 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환될 수 있으며, 이때 상기 치환기가 복수인 경우, 이들은 서로 동일하거나 상이할 수 있다.Alkyl group of the R 1, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkyl boron group, an aryl boron group, The arylphosphine group, the arylphosphine oxide group and the arylamine group are each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 Alkynyl group of ˜C 40 , cycloalkyl group of C 3 ˜C 40 , heterocycloalkyl group of 3 to 40 nuclear atoms, aryl group of C 6 ˜C 60 , heteroaryl group of 5 to 60 nuclear atoms, C 1 ˜ C 40 alkyloxy group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ for C 60 aryl boron group, C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 aryl phosphine oxide group, and a C 6 ~ one or more substituents selected from the group consisting of an aryl amine of the C 60 of the It may be substituted, and wherein when the substituent is plural, they may be the same or different from each other.
상기 화학식 2로 표시되는 치환체는 하기 화학식 A-1 내지 A-15로 구성되는 치환체 군 중 어느 하나로 보다 구체화될 수 있다. Substituents represented by the formula (2) may be more embodied in any one of the substituent group consisting of the formula A-1 to A-15.
상기 A-1 내지 A-15에서,In the above A-1 to A-15,
R1은 전술한 화학식 2에서 정의된 바와 같고,R 1 is as defined in Formula 2 above,
n은 0 내지 4의 정수로서, 상기 n이 0인 경우, 수소가 치환기 R2로 치환되지 않는 것을 의미하고, 상기 n이 1 내지 4의 정수인 경우, R2는 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40 60의 아릴옥시기 C1~C40의 알킬옥시기, C6~C40의 아릴아민기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C40의 아릴보론기, C6~C40의 아릴포스핀기, C6~C40의 아릴포스핀옥사이드기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택되거나, 또는 인접하는 기(예컨대, L1, R1 또는 다른 R2 등)와 결합하여 축합 고리를 형성할 수 있으며,n is an integer of 0 to 4, when n is 0, it means that hydrogen is not substituted with a substituent R 2 , when n is an integer of 1 to 4, R 2 is deuterium, halogen, cyano group, nitro C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 Aryl group of ~ C 40 , heteroaryl group of 5 to 40 nuclear atoms, aryloxy group of C 6 ~ C 40 60 C 1 ~ C 40 alkyloxy group, C 6 ~ C 40 arylamine group, C 1 ~ C 40 alkyl silyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 40 aryl boron group, C 6 ~ C 40 aryl phosphine group, C 6 ~ aryl phosphine oxide of a C 40 group, and C 6 ~ C 40 It may be selected from the group consisting of arylsilyl groups, or may be combined with adjacent groups (eg, L 1 , R 1 or other R 2, etc.) to form a condensed ring,
상기 R2의 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C40의 아릴보론기, C6~C40의 아릴포스핀기, C6~C40의 아릴포스핀옥사이드기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환될 수 있으며, 이때 상기 치환기가 복수인 경우, 이들은 서로 동일하거나 상이할 수 있다.Alkyl group of the R 2, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, The arylphosphine group, the arylphosphine oxide group and the arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alky Neyl group, C 6 ~ C 40 aryl group, C 5 ~ C 40 heteroaryl group, C 6 ~ C 40 aryloxy group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 40 arylamine group, an aryl boronic of C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkyl silyl group, C 1 ~ C 40 group of an alkyl boron, C 6 ~ C 40 group, C 6 ~ C 40 aryl phosphine group, C 6 ~ C 40 aryl phosphine oxide group, and a C 6 ~ C 40 aryl silyl optionally substituted with one or more substituents selected from the group consisting of In this case, when the substituents are plural, they may be the same or different from each other.
또한 본 발명에 따른 화학식 1로 표시되는 화합물에서, Ar1은 하기 화학식 3으로 표시되는 치환체일 수 있다. In addition, in the compound represented by Chemical Formula 1 according to the present invention, Ar 1 may be a substituent represented by the following Chemical Formula 3.
상기 화학식 3에서,In Chemical Formula 3,
*는 상기 화학식 1에 결합되는 부분을 의미하고,* Means a moiety bonded to Formula 1,
Z는 서로 동일하거나 또는 상이하며, 각각 독립적으로 N 또는 C(R3)이고, 다만 복수의 Z 중 적어도 하나는 N인 것이 바람직하다. Z is the same as or different from each other, and each independently N or C (R 3 ), but preferably at least one of the plurality of Z is N.
또한 R3이 복수인 경우, 복수의 R3은 서로 동일하거나 상이하며, 각각 독립적으로 수소, 중수소(D), 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 또는 인접하는 기(예컨대, 다른 R3)와 결합하여 축합 고리를 형성할 수 있다. 이때, R3은 수소, C1~C40의 알킬기, C6~C40의 아릴기, 및 핵원자수 5 내지 40의 헤테로아릴기로 구성된 군에서 선택되는 것이 바람직하다. In addition, when the R 3 is plural, plural R 3 may be the same or different, each independently represent hydrogen, deuterium (D), a halogen, a cyano group, a nitro group, an alkyl group of C 1 ~ C 40, C 2 ~ C 40 Alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 to C 60 aryl group, nuclear atom 5 to 60 hetero aryl group, C 1 ~ C 40 of the alkyloxy group, C 6 ~ C 60 of the aryloxy group, C 1 ~ C 40 alkyl silyl group, the group C 6 ~ C 60 aryl silyl, C 1 ~ C 40 alkyl boron group, C 6 ~ C group 60 arylboronic of, C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 aryl phosphine oxide group, and a C 6 ~, or selected from the group consisting of an aryl amine of the C 60 of, Or combine with adjacent groups (eg, other R 3 ) to form a condensed ring. In this case, R 3 is preferably selected from the group consisting of hydrogen, a C 1 ~ C 40 alkyl group, C 6 ~ C 40 aryl group, and a heteroaryl group of 5 to 40 nuclear atoms.
X는 O 또는 S일 수 있다.X may be O or S.
R4 내지 R5는 서로 동일하거나 또는 상이하며, 각각 독립적으로 수소, 중수소(D), 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 또는 인접하는 기(예, R3)와 결합하여 축합 고리를 형성할 수 있다.R 4 to R 5 are the same or different and are each independently hydrogen, deuterium (D), a halogen, a cyano group, a nitro group, C 1 ~ alkenyl group of the C 40 alkyl group, C 2 ~ C 40 of, C 2 Alkynyl group of ˜C 40 , cycloalkyl group of C 3 ˜C 40 , heterocycloalkyl group of 3 to 40 nuclear atoms, aryl group of C 6 ˜C 60 , heteroaryl group of 5 to 60 nuclear atoms, C 1 ˜ C 40 alkyloxy group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ an aryl boronic of C 60, C 6 ~ C 60 aryl phosphine group, a group of C 6 ~ C 60 aryl phosphine oxide group, and a C 6 ~ selected from the group consisting of an aryl amine of the C 60 of or, or adjacent (e.g., , R 3 ) may be combined to form a condensed ring.
본 발명에서, R4는 C6~C18의 아릴기인 것이 바람직하며, R5는 수소, C1~C40의 알킬기, C6~C40의 아릴기, 및 핵원자수 5 내지 40의 헤테로아릴기로 구성된 군에서 선택되는 것이 바람직하다. 구체적으로, R4는 페닐, 비페닐, 터페닐, 나프틸, 및 트리페닐렌으로 이루어진 군에서 선택될 수 있다.In the present invention, it is preferable that R 4 is a C 6 ~ C 18 aryl group, R 5 is hydrogen, C 1 ~ C 40 alkyl group, C 6 ~ C 40 aryl group, and a nuclear atom of 5 to 40 hetero It is preferably selected from the group consisting of aryl groups. Specifically, R 4 may be selected from the group consisting of phenyl, biphenyl, terphenyl, naphthyl, and triphenylene.
n은 0 내지 7의 정수이고, n이 2 이상인 경우 복수의 R5는 서로 동일하거나 상이할 수 있다. 여기서, n이 0인 경우, 수소가 치환기 R5로 치환되지 않는 것을 의미하고, 상기 n이 1 내지 7인 경우, R5는 수소를 제외한 전술한 치환기를 각각 독립적으로 가질 수 있다. n is an integer of 0 to 7, and when n is 2 or more, a plurality of R 5 may be the same or different from each other. Herein, when n is 0, it means that hydrogen is not substituted with a substituent R 5 , and when n is 1 to 7, R 5 may independently have the aforementioned substituents except for hydrogen.
상기 R3 내지 R5에서 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기 및 아릴아민기는 각각 독립적으로 수소, 중수소(D), 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환될 수 있으며, 이때 상기 치환기가 복수인 경우, 이들은 서로 동일하거나 상이할 수 있다.Alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkyl boron group, aryl in the R 3 to R 5 boron group, an aryl phosphine group, aryl phosphine oxide group and an arylamine group each independently hydrogen, deuterium (D), a halogen, a cyano group, a nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group , C 2 ~ C 40 Alkynyl group, C 3 ~ C 40 Cycloalkyl group, C 3 ~ C 40 heterocycloalkyl group, C 6 ~ C 60 Aryl group, Nuclear atoms 5 to 60 heteroaryl group, C 1 -C 40 alkyloxy group, C 6 -C 60 aryloxy group, C 1 -C 40 alkylsilyl group, C 6 -C 60 arylsilyl group, C 1 -C 40 alkylboron group, aryl of C 6 ~ C 60 boron group, C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 aryl phosphine oxide group, and a C 6 ~ at least one selected from the group consisting of C 60 arylamine It may be substituted with a substituent, wherein when the substituent is plural, they may be the same or different from each other.
상기 화학식 3으로 표시되는 치환체의 바람직한 일례를 들면, 하기 화학식 4로 구체화될 수 있다. For example, a preferred example of the substituent represented by Formula 3 may be embodied by the following formula (4).
상기 화학식 4에서, In Chemical Formula 4,
Z와 R4는 각각 전술한 화학식 3에서 정의된 바와 같다. Z and R 4 are each as defined in Chemical Formula 3 described above.
이상에서 설명한 본 발명의 화학식 1로 표시되는 화합물은 하기 예시되는 화학식 1-1 내지 화학식 7-23 중 어느 하나로 표시되는 화합물로 보다 구체화될 수 있다. 그러나 본 발명의 화학식 1로 표시되는 화합물이 하기 예시된 것들에 의해 한정되는 것은 아니다.The compound represented by the formula (1) of the present invention described above may be more specifically represented by the compound represented by any one of formulas 1-1 to 7-23 illustrated below. However, the compound represented by the formula (1) of the present invention is not limited by those illustrated below.
본 발명에서 "알킬"은 탄소수 1 내지 40의 직쇄 또는 측쇄의 포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이의 예로는 메틸, 에틸, 프로필, 이소부틸, sec-부틸, 펜틸, iso-아밀, 헥실 등을 들 수 있으나, 이에 한정되지는 않는다."Alkyl" in the present invention means a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl and the like.
본 발명에서 "알케닐(alkenyl)"은 탄소-탄소 이중 결합을 1개 이상 가진탄소수 2 내지 40의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이의 예로는 비닐(vinyl), 알릴(allyl), 이소프로펜일(isopropenyl), 2-부텐일(2-butenyl) 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, "alkenyl" refers to a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon double bond. Examples thereof include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like.
본 발명에서 "알키닐(alkynyl)"은 탄소-탄소 삼중 결합을 1개 이상 가진 탄소수 2 내지 40의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이의 예로는 에티닐(ethynyl), 2-프로파닐(2-propynyl) 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, "alkynyl" refers to a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon triple bond. Examples thereof include, but are not limited to, ethynyl, 2-propynyl, and the like.
본 발명에서 "아릴"은 단독 고리 또는 2이상의 고리가 조합된 탄소수 6 내지 40의 방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 또한, 2 이상의 고리가 서로 단순 부착(pendant)되거나 축합된 형태도 포함될 수 있다. 이러한 아릴의 예로는 페닐, 나프틸, 페난트릴, 안트릴 등을 들 수 있으나, 이에 한정되지는 않는다."Aryl" in the present invention means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 40 carbon atoms combined with a single ring or two or more rings. In addition, a form in which two or more rings are attached to each other (pendant) or condensed may also be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.
본 발명에서 "헤테로아릴"은 핵원자수 5 내지 40의 모노헤테로사이클릭 또는 폴리헤테로사이클릭 방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 이때, 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3개의 탄소가 N, O, S 또는 Se와 같은 헤테로원자로 치환된다. 또한, 2 이상의 고리가 서로 단순 부착(pendant)되거나 축합된 형태도 포함될 수 있고, 나아가 아릴기와의 축합된 형태도 포함될 수 있다. 이러한 헤테로아릴의 예로는 피리딜, 피라지닐, 피리미디닐, 피리다지닐, 트리아지닐과 같은 6-원 모노사이클릭 고리, 페녹사티에닐(phenoxathienyl), 인돌리지닐(indolizinyl), 인돌릴(indolyl), 퓨리닐(purinyl), 퀴놀릴(quinolyl), 벤조티아졸(benzothiazole), 카바졸릴(carbazolyl)과 같은 폴리사이클릭 고리 및 2-퓨라닐, N-이미다졸릴, 2-이속사졸릴, 2-피리디닐, 2-피리미디닐 등을 들 수 있으나, 이에 한정되지는 않는다."Heteroaryl" as used herein means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclear atoms. At least one carbon in the ring, preferably 1 to 3 carbons, is substituted with a heteroatom such as N, O, S or Se. In addition, a form in which two or more rings are pendant or condensed with each other may be included, and may also include a form in which the two or more rings are condensed with an aryl group. Examples of such heteroaryl include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolinzinyl, indolyl ( polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, carbazolyl and 2-furanyl, N-imidazolyl, 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.
본 발명에서 "아릴옥시"는 RO-로 표시되는 1가의 치환기로, 상기 R은 탄소수 5 내지 40의 아릴을 의미한다. 이러한 아릴옥시의 예로는 페닐옥시, 나프틸옥시, 디페닐옥시 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, "aryloxy" is a monovalent substituent represented by RO-, wherein R means aryl having 5 to 40 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.
본 발명에서 "알킬옥시"는 R'O-로 표시되는 1가의 치환기로, 상기 R'는 탄소수 1 내지 40의 알킬을 의미하며, 직쇄(linear), 측쇄(branched) 또는 사이클릭(cyclic) 구조를 포함할 수 있다. 알킬옥시의 예로는 메톡시, 에톡시, n-프로폭시, 1-프로폭시, t-부톡시, n-부톡시, 펜톡시 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, "alkyloxy" is a monovalent substituent represented by R'O-, wherein R 'means an alkyl having 1 to 40 carbon atoms, linear, branched or cyclic structure It may include. Examples of alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.
본 발명에서 "아릴아민"은 탄소수 6 내지 40의 아릴로 치환된 아민을 의미한다."Arylamine" in the present invention means an amine substituted with aryl having 6 to 40 carbon atoms.
본 발명에서 "시클로알킬"은 탄소수 3 내지 40의 모노사이클릭 또는 폴리사이클릭 비-방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 이러한 사이클로알킬의 예로는 사이클로프로필, 사이클로펜틸, 사이클로헥실, 노르보닐(norbornyl), 아다만틴(adamantine) 등을 들 수 있으나, 이에 한정되지는 않는다."Cycloalkyl" as used herein means monovalent substituents derived from monocyclic or polycyclic non-aromatic hydrocarbons having 3 to 40 carbon atoms. Examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
본 발명에서 "헤테로시클로알킬"은 핵원자수 3 내지 40의 비-방향족 탄화수소로부터 유래된 1가의 치환기를 의미하며, 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3개의 탄소가 N, O, S 또는 Se와 같은 헤테로 원자로 치환된다. 이러한 헤테로시클로알킬의 예로는 모르폴린, 피페라진 등을 들 수 있으나, 이에 한정되지는 않는다.By "heterocycloalkyl" is meant monovalent substituents derived from non-aromatic hydrocarbons having 3 to 40 nuclear atoms, wherein at least one carbon in the ring, preferably 1 to 3 carbons, is N, O, S Or a hetero atom such as Se. Examples of such heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.
본 발명에서 "알킬실릴"은 탄소수 1 내지 40의 알킬로 치환된 실릴이고, "아릴실릴"은 탄소수 5 내지 40의 아릴로 치환된 실릴을 의미한다.In the present invention, "alkylsilyl" means silyl substituted with alkyl having 1 to 40 carbon atoms, and "arylsilyl" means silyl substituted with aryl having 5 to 40 carbon atoms.
본 발명에서 "축합고리"는 축합 지방족 고리, 축합 방향족 고리, 축합 헤테로지방족 고리, 축합 헤테로방향족 고리 또는 이들의 조합된 형태를 의미한다.As used herein, the term “condensed ring” means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.
<유기 전계 발광 소자><Organic EL device>
한편, 본 발명의 다른 측면은 상기한 본 발명에 따른 화학식 1로 표시되는 화합물을 포함하는 유기 전계 발광 소자(유기 EL 소자)에 관한 것이다.On the other hand, another aspect of the present invention relates to an organic electroluminescent device (organic EL device) comprising the compound represented by the formula (1) according to the present invention.
보다 구체적으로, 본 발명에 따른 유기 전계 발광 소자는 양극(anode), 음극(cathode) 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하며, 상기 1층 이상의 유기물층 중 적어도 하나는 상기 화학식 1로 표시되는 화합물을 포함한다. 이때, 상기 화합물은 단독으로 사용되거나, 또는 2 이상이 혼합되어 사용될 수 있다.More specifically, the organic electroluminescent device according to the present invention includes an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode, and at least one of the one or more organic material layers. Includes a compound represented by the formula (1). In this case, the compound may be used alone, or two or more may be used in combination.
상기 1층 이상의 유기물층은 정공주입층, 정공수송층, 발광보조층, 발광층, 전자수송층 및 전자주입층 중 어느 하나 이상일 수 있고, 이 중에서 적어도 하나의 유기물층은 상기 화학식 1로 표시되는 화합물을 포함할 수 있다. 구체적으로 상기 화학식 1의 화합물을 포함하는 유기물층은 발광층, 전자수송층, 정공수송층인 것이 바람직하다.The one or more organic material layers may be any one or more of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport layer and an electron injection layer, wherein at least one organic material layer may include a compound represented by Formula 1 have. Specifically, the organic material layer including the compound of Formula 1 is preferably a light emitting layer, an electron transport layer, a hole transport layer.
본 발명의 유기 전계 발광 소자의 발광층은 호스트 재료를 포함할 수 있는데, 이때 호스트 재료로서 상기 화학식 1의 화합물을 포함할 수 있다. 또한 본 발명의 유기 전계 발광 소자의 발광층은 상기 화학식 1의 화합물 이외의 화합물을 호스트로 포함할 수 있다.The light emitting layer of the organic electroluminescent device of the present invention may include a host material, and may include the compound of Formula 1 as the host material. In addition, the light emitting layer of the organic electroluminescent device of the present invention may include a compound other than the compound of Formula 1 as a host.
상기 화학식 1로 표시되는 화합물을 유기 전계 발광 소자의 발광층 재료, 바람직하게는 청색, 녹색, 적색의 인광 호스트 재료로 포함할 경우, 발광층에서 정공과 전자의 결합력이 높아지기 때문에, 유기 전계 발광 소자의 효율(발광효율 및 전력효율), 수명, 휘도 및 구동전압 등을 향상시킬 수 있다. 구체적으로 상기 화학식 1로 표시되는 화합물은 녹색 및/또는 적색의 인광 호스트, 형광 호스트, 또는 도펀트 재료로서 유기 전계 발광 소자에 포함되는 것이 바람직하다. 특히, 본 발명의 화학식 1로 표시되는 화합물은 발광층의 인광 호스트, 형광 호스트 또는 도펀트 재료인 것이 바람직하며, 발광층의 인광 호스트인 것이 더욱 바람직하다.When the compound represented by Chemical Formula 1 is included as a light emitting layer material of the organic electroluminescent device, preferably a blue, green, or red phosphorescent host material, the binding force between the holes and the electrons in the light emitting layer increases, so that the efficiency of the organic electroluminescent device (Luminescence efficiency and power efficiency), lifetime, brightness and driving voltage can be improved. Specifically, the compound represented by Chemical Formula 1 is preferably included in the organic electroluminescent device as a green and / or red phosphorescent host, fluorescent host, or dopant material. In particular, the compound represented by Formula 1 of the present invention is preferably a phosphorescent host, a fluorescent host or a dopant material of the light emitting layer, and more preferably a phosphorescent host of the light emitting layer.
이러한 본 발명의 유기 전계 발광 소자의 구조는 특별히 한정되지 않으나, 기판, 양극, 정공주입층, 정공수송층, 발광보조층, 발광층, 전자수송층 및 음극이 순차적으로 적층된 구조일 수 있다. 이때, 상기 정공주입층, 정공수송층, 발광보조층, 발광층, 전자수송층 및 전자주입층 중 하나 이상은 상기 화학식 1로 표시되는 화합물을 포함할 수 있고, 바람직하게는 정공수송층, 전자저지층, 발광보조층이 상기 화학식 1로 표시되는 화합물을 포함할 수 있다. 한편 상기 전자수송층 위에는 전자주입층이 추가로 적층될 수 있다.The structure of the organic EL device of the present invention is not particularly limited, but may be a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport layer, and a cathode are sequentially stacked. In this case, at least one of the hole injection layer, the hole transport layer, the light emitting auxiliary layer, the light emitting layer, the electron transport layer and the electron injection layer may include a compound represented by the formula (1), preferably a hole transport layer, electron blocking layer, light emission The auxiliary layer may include a compound represented by Chemical Formula 1. Meanwhile, an electron injection layer may be further stacked on the electron transport layer.
본 발명의 유기 전계 발광 소자의 구조는 전극과 유기물층 계면에 절연층 또는 접착층이 삽입된 구조일 수 있다.The organic electroluminescent device of the present invention may have a structure in which an insulating layer or an adhesive layer is inserted between an electrode and an organic material layer interface.
본 발명의 유기 전계 발광 소자는 상기 유기물층 중 1층 이상이 상기 화학식 1로 표시되는 화합물을 포함하는 것을 제외하고는, 당업계에 공지된 재료 및 방법으로 유기물층 및 전극을 형성하여 제조할 수 있다.The organic electroluminescent device of the present invention can be manufactured by forming an organic material layer and an electrode by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound represented by Chemical Formula 1.
상기 유기물층은 진공 증착법이나 용액 도포법에 의하여 형성될 수 있다. 상기 용액 도포법의 예로는 스핀 코팅, 딥코팅, 닥터 블레이딩, 잉크젯 프린팅 또는 열 전사법 등이 있으나, 이에 한정되지는 않는다.The organic material layer may be formed by a vacuum deposition method or a solution coating method. Examples of the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.
본 발명의 유기 전계 발광 소자 제조 시 사용되는 기판은 특별히 한정되지 않으나, 실리콘 웨이퍼, 석영, 유리판, 금속판, 플라스틱 필름 및 시트 등을 사용할 수 있다.The substrate used in the manufacture of the organic EL device of the present invention is not particularly limited, but silicon wafers, quartz, glass plates, metal plates, plastic films, sheets, and the like may be used.
또, 양극 물질로는 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연산화물, 인듐산화물, 인듐 주석 산화물(ITO), 인듐 아연 산화물(IZO)과 같은 금속 산화물; ZnO:Al 또는 SnO2:Sb와 같은 금속과 산화물의 조합; 폴리티오펜, 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜](PEDT), 폴리피롤 또는 폴리아닐린과 같은 전도성 고분자; 및 카본블랙 등을 들 수 있으나, 이에 한정되지는 않는다.In addition, examples of the anode material include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole or polyaniline; And carbon black, but are not limited thereto.
또, 음극 물질로는 마그네슘, 칼슘, 나트륨, 칼륨, 타이타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석, 또는 납과 같은 금속 또는 이들의 합금; 및 LiF/Al 또는 LiO2/Al과 같은 다층 구조 물질 등을 들 수 있으나, 이에 한정되지는 않는다.The negative electrode material may be a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or an alloy thereof; And multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like, but are not limited thereto.
또한, 정공 주입층, 정공 수송층, 전자 주입층 및 전자 수송층은 특별히 한정되는 것은 아니며, 당 업계에 알려진 통상의 물질을 사용할 수 있다.In addition, the hole injection layer, the hole transport layer, the electron injection layer and the electron transport layer is not particularly limited, and conventional materials known in the art may be used.
이하 본 발명을 실시예를 통하여 상세히 설명하면 다음과 같다. 단, 하기 실시예는 본 발명을 예시하는 것일 뿐, 본 발명이 하기 실시예에 의해 한정되는 것은 아니다.Hereinafter, the present invention will be described in detail with reference to the following Examples. However, the following Examples are merely to illustrate the present invention, the present invention is not limited by the following Examples.
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준비예Preparation
1] Core-1의 합성 1] Synthesis of Core-1
<단계 1> Core-1의 합성<Step 1> Synthesis of Core-1
질소 기류 하에서 2-bromo-9H-carbazole (250 g, 1016 mmol), Phenylboronic acid (136.2 g, 1117 mmol), Pd(PPh3)4 (58.7 g, 50.8 mmol), K2CO3
(421.2 g, 3048 mmol), 1,4-dioxane/H2O (2000 ml/500 ml)를 혼합하고 120℃에서 4시간 동안 교반하였다.2-bromo-9H-carbazole (250 g, 1016 mmol), Phenylboronic acid (136.2 g, 1117 mmol), Pd (PPh 3 ) 4 (58.7 g, 50.8 mmol), K 2 CO 3 under nitrogen stream (421.2 g, 3048 mmol), 1,4-dioxane / H 2 O (2000 ml / 500 ml) were mixed and stirred at 120 ° C. for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 여과하였다. 얻어진 유기층에서 용매를 제거한 후 컬럼 크로마토그래피 (Hexane : EA = 4:1 (v/v))로 정제하여 Core-1 (215 g, 수율 87%)을 얻었다. After the reaction was terminated and extracted with methylene chloride, MgSO 4 was added and filtered. After removing the solvent from the obtained organic layer was purified by column chromatography (Hexane: EA = 4: 1 (v / v)) to give Core-1 (215 g, 87% yield).
1H-NMR: δ 7.45-7.51 (m, 4H), 7.67-7.68 (m, 2H), 7.70-7.78 (m, 4H), 8.20 (d, 1H), 8.24 (d, 1H), 10.2 (b, 1H) 1 H-NMR: δ 7.45-7.51 (m, 4H), 7.67-7.68 (m, 2H), 7.70-7.78 (m, 4H), 8.20 (d, 1H), 8.24 (d, 1H), 10.2 (b , 1H)
[[
준비예Preparation
2] Core-2의 합성 2] Synthesis of Core-2
<단계 1> Core-2의 합성<Step 1> Synthesis of Core-2
질소 기류 하에서 2-bromo-9H-carbazole (250 g, 1016 mmol), [1,1'-biphenyl]-3-ylboronic acid (221.2 g, 1117 mmol), Pd(PPh3)4 (58.7 g, 50.8 mmol), K2CO3
(421.2 g, 3048 mmol), 1,4-dioxane/H2O (2000 ml/500 ml)를 혼합하고 120℃에서 4시간 동안 교반하였다.2-bromo-9H-carbazole (250 g, 1016 mmol), [1,1'-biphenyl] -3-ylboronic acid (221.2 g, 1117 mmol), Pd (PPh 3 ) 4 (58.7 g, 50.8) under nitrogen stream mmol), K 2 CO 3 (421.2 g, 3048 mmol), 1,4-dioxane / H 2 O (2000 ml / 500 ml) were mixed and stirred at 120 ° C. for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 여과하였다. 얻어진 유기층에서 용매를 제거한 후 컬럼 크로마토그래피 (Hexane : EA = 4:1 (v/v))로 정제하여 Core-2 (272.5 g, 수율 84%)를 얻었다. After the reaction was terminated and extracted with methylene chloride, MgSO 4 was added and filtered. The solvent was removed from the organic layer and purified by column chromatography (Hexane: EA = 4: 1 (v / v)) to obtain Core-2 (272.5 g, 84% yield).
1H-NMR: δ 7.49-7.53 (m, 4H), 7.67-7.68 (m, 2H), 7.71-7.79 (m, 6H), 7.94 (s, 1H), 8.20 (d, 1H), 8.23 (d, 1H), 10.1 (b, 1H) 1 H-NMR: δ 7.49-7.53 (m, 4H), 7.67-7.68 (m, 2H), 7.71-7.79 (m, 6H), 7.94 (s, 1H), 8.20 (d, 1H), 8.23 (d , 1H), 10.1 (b, 1H)
[[
준비예Preparation
3] Core-3의 합성 3] Synthesis of Core-3
<단계 1> Core-3의 합성<Step 1> Synthesis of Core-3
질소 기류 하에서 2-bromo-9H-carbazole (250 g, 1016 mmol), [1,1'-biphenyl]-4-ylboronic acid (221.2 g, 1117 mmol), Pd(PPh3)4 (58.7 g, 50.8 mmol), K2CO3
(421.2 g, 3048 mmol), 1,4-dioxane/H2O (2000 ml/500 ml)를 혼합하고 120℃에서 4시간 동안 교반하였다.2-bromo-9H-carbazole (250 g, 1016 mmol), [1,1'-biphenyl] -4-ylboronic acid (221.2 g, 1117 mmol), Pd (PPh 3 ) 4 (58.7 g, 50.8) under nitrogen stream mmol), K 2 CO 3 (421.2 g, 3048 mmol), 1,4-dioxane / H 2 O (2000 ml / 500 ml) were mixed and stirred at 120 ° C. for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 여과하였다. 얻어진 유기층에서 용매를 제거한 후 컬럼 크로마토그래피 (Hexane : EA = 4:1 (v/v))로 정제하여 Core-3 (272.5 g, 수율 84%)을 얻었다. After the reaction was terminated and extracted with methylene chloride, MgSO 4 was added and filtered. After removing the solvent in the organic layer obtained was purified by column chromatography (Hexane: EA = 4: 1 (v / v)) to give Core-3 (272.5 g, 84% yield).
1H-NMR: δ 7.46-7.50 (m, 4H), 7.67-7.68 (m, 2H), 7.70-7.81 (m, 7H), 8.22 (d, 1H), 8.25 (d, 1H), 10.3 (b, 1H) 1 H-NMR: δ 7.46-7.50 (m, 4H), 7.67-7.68 (m, 2H), 7.70-7.81 (m, 7H), 8.22 (d, 1H), 8.25 (d, 1H), 10.3 (b , 1H)
[[
준비예Preparation
4] Core-4의 합성 4] Synthesis of Core-4
<단계 1> Core-4의 합성<Step 1> Synthesis of Core-4
질소 기류 하에서 2-bromo-9H-carbazole (250 g, 1016 mmol), [1,1'-biphenyl]-2-ylboronic acid (221.2 g, 1117 mmol), Pd(PPh3)4 (58.7 g, 50.8 mmol), K2CO3
(421.2 g, 3048 mmol), 1,4-dioxane/H2O (2000 ml/500 ml)를 혼합하고 120℃에서 4시간 동안 교반하였다.2-bromo-9H-carbazole (250 g, 1016 mmol), [1,1'-biphenyl] -2-ylboronic acid (221.2 g, 1117 mmol), Pd (PPh 3 ) 4 (58.7 g, 50.8) under nitrogen stream mmol), K 2 CO 3 (421.2 g, 3048 mmol), 1,4-dioxane / H 2 O (2000 ml / 500 ml) were mixed and stirred at 120 ° C. for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 여과하였다. 얻어진 유기층에서 용매를 제거한 후 컬럼 크로마토그래피 (Hexane : EA = 4:1 (v/v))로 정제하여 Core-4 (272.5 g, 수율 84%)를 얻었다. After the reaction was terminated and extracted with methylene chloride, MgSO 4 was added and filtered. After removing the solvent in the organic layer obtained was purified by column chromatography (Hexane: EA = 4: 1 (v / v)) to give Core-4 (272.5 g, 84% yield).
1H-NMR: δ 7.48-7.52 (m, 4H), 7.65-7.68 (m, 2H), 7.71-7.80 (m, 7H), 8.24 (d, 1H), 8.26 (d, 1H), 10.0 (b, 1H) 1 H-NMR: δ 7.48-7.52 (m, 4H), 7.65-7.68 (m, 2H), 7.71-7.80 (m, 7H), 8.24 (d, 1H), 8.26 (d, 1H), 10.0 (b , 1H)
[[
준비예Preparation
5] Core-5의 합성 5] Synthesis of Core-5
<단계 1> Core-5의 합성<Step 1> Synthesis of Core-5
질소 기류 하에서 2-bromo-9H-carbazole (250 g, 1016 mmol), [1,1':3',1''-terphenyl]-5'-ylboronic acid (306.3 g, 1117 mmol), Pd(PPh3)4 (58.7 g, 50.8 mmol), K2CO3
(421.2 g, 3048 mmol), 1,4-dioxane/H2O (2000 ml/500 ml)를 혼합하고 120℃에서 4시간 동안 교반하였다.2-bromo-9H-carbazole (250 g, 1016 mmol), [1,1 ': 3', 1 ''-terphenyl] -5'-ylboronic acid (306.3 g, 1117 mmol), Pd (PPh) under nitrogen stream 3 ) 4 (58.7 g, 50.8 mmol), K 2 CO 3 (421.2 g, 3048 mmol), 1,4-dioxane / H 2 O (2000 ml / 500 ml) were mixed and stirred at 120 ° C. for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 여과하였다. 얻어진 유기층에서 용매를 제거한 후 컬럼 크로마토그래피 (Hexane : EA = 4:1 (v/v))로 정제하여 Core-5 (353.5 g, 수율 88%)를 얻었다. After the reaction was terminated and extracted with methylene chloride, MgSO 4 was added and filtered. After removing the solvent in the obtained organic layer was purified by column chromatography (Hexane: EA = 4: 1 (v / v)) to give Core-5 (353.5 g, yield 88%).
1H-NMR: δ 7.49-7.54 (m, 6H), 7.66-7.70 (m, 2H), 7.74-7.82 (m, 6H), 8.01 (s, 2H), 8.03 (s, 1H), 8.21 (d, 1H), 8.24 (d, 1H), 10.2 (b, 1H) 1 H-NMR: δ 7.49-7.54 (m, 6H), 7.66-7.70 (m, 2H), 7.74-7.82 (m, 6H), 8.01 (s, 2H), 8.03 (s, 1H), 8.21 (d , 1H), 8.24 (d, 1H), 10.2 (b, 1H)
[[
준비예Preparation
6] Core-6의 합성 6] Synthesis of Core-6
<단계 1> Core-6의 합성<Step 1> Synthesis of Core-6
질소 기류 하에서 2-bromo-9H-carbazole (250 g, 1016 mmol), naphthalen-2-ylboronic acid (192.2 g, 1117 mmol), Pd(PPh3)4 (58.7 g, 50.8 mmol), K2CO3
(421.2 g, 3048 mmol), 1,4-dioxane/H2O (2000 ml/500 ml)를 혼합하고 120℃에서 4시간 동안 교반하였다.2-bromo-9H-carbazole (250 g, 1016 mmol), naphthalen-2-ylboronic acid (192.2 g, 1117 mmol), Pd (PPh 3 ) 4 (58.7 g, 50.8 mmol), K 2 CO 3 under nitrogen stream (421.2 g, 3048 mmol), 1,4-dioxane / H 2 O (2000 ml / 500 ml) were mixed and stirred at 120 ° C. for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 여과하였다. 얻어진 유기층에서 용매를 제거한 후 컬럼 크로마토그래피 (Hexane : EA = 4:1 (v/v))로 정제하여 Core-6 (262.2 g, 수율 88%)을 얻었다. After the reaction was terminated and extracted with methylene chloride, MgSO 4 was added and filtered. After removing the solvent in the organic layer obtained was purified by column chromatography (Hexane: EA = 4: 1 (v / v)) to give Core-6 (262.2 g, yield 88%).
1H-NMR: δ 7.49-7.54 (m, 4H), 7.64 (s, 1H), 7.66-7.70 (m, 2H), 7.74-7.79 (m, 3H), 7.95(d, 1H), 8.01 (d, 1H), 8.20 (d, 1H), 8.23 (d, 1H), 10.1 (b, 1H) 1 H-NMR: δ 7.49-7.54 (m, 4H), 7.64 (s, 1H), 7.66-7.70 (m, 2H), 7.74-7.79 (m, 3H), 7.95 (d, 1H), 8.01 (d , 1H), 8.20 (d, 1H), 8.23 (d, 1H), 10.1 (b, 1H)
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준비예Preparation
7] Core-7의 합성 7] Synthesis of Core-7
<단계 1> Core-7의 합성<Step 1> Synthesis of Core-7
질소 기류 하에서 2-bromo-9H-carbazole (250 g, 1016 mmol), naphthalen-2-ylboronic acid (192.2 g, 1117 mmol), Pd(PPh3)4 (58.7 g, 50.8 mmol), K2CO3
(421.2 g, 3048 mmol), 1,4-dioxane/H2O (2000 ml/500 ml)를 혼합하고 120℃에서 4시간 동안 교반하였다.2-bromo-9H-carbazole (250 g, 1016 mmol), naphthalen-2-ylboronic acid (192.2 g, 1117 mmol), Pd (PPh 3 ) 4 (58.7 g, 50.8 mmol), K 2 CO 3 under nitrogen stream (421.2 g, 3048 mmol), 1,4-dioxane / H 2 O (2000 ml / 500 ml) were mixed and stirred at 120 ° C. for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 여과하였다. 얻어진 유기층에서 용매를 제거한 후 컬럼 크로마토그래피 (Hexane : EA = 4:1 (v/v))로 정제하여 Core-7 (262.2 g, 수율 88%)을 얻었다. After the reaction was terminated and extracted with methylene chloride, MgSO 4 was added and filtered. After removing the solvent in the obtained organic layer was purified by column chromatography (Hexane: EA = 4: 1 (v / v)) to give Core-7 (262.2 g, 88% yield).
1H-NMR: δ 7.46-7.50 (m, 4H), 7.66-7.79 (m, 2H), 7.74-7.79 (m, 4H), 7.97(d, 1H), 8.02 (d, 1H), 8.18 (d, 1H), 8.22 (d, 1H), 10.3 (b, 1H) 1 H-NMR: δ 7.46-7.50 (m, 4H), 7.66-7.79 (m, 2H), 7.74-7.79 (m, 4H), 7.97 (d, 1H), 8.02 (d, 1H), 8.18 (d , 1H), 8.22 (d, 1H), 10.3 (b, 1H)
[[
합성예Synthesis Example
1] 1-1의 합성 1] Synthesis of 1-1
질소 기류 하에서 Core-1 (10 g, 41.1 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (12.1 g, 45.2 mmol), CuI (0.783 g, 4.11 mmol), 1,10-phenanthroline (1.48 g, 8.22 mmol), Cs2CO3 (26.8 g, 82.2 mmol) 및 nitrobenzene (100 ml)를 혼합하고 210℃ 에서 3시간 동안 교반하였다. 반응이 종결된 후 고체염을 필터링한 후, 컬럼 크로마토그래피로 정제하여 목적 화합물인 1-1 (12.1 g, 수율 62%)을 얻었다.Core-1 (10 g, 41.1 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (12.1 g, 45.2 mmol), CuI (0.783 g, 4.11 mmol), 1, under a nitrogen stream. 10-phenanthroline (1.48 g, 8.22 mmol), Cs 2 CO 3 (26.8 g, 82.2 mmol) and nitrobenzene (100 ml) were mixed and stirred at 210 ° C. for 3 hours. After the reaction was terminated, the solid salt was filtered and purified by column chromatography to obtain the title compound 1-1 (12.1 g, yield 62%).
Mass (이론치: 474.57, 측정치: 475(M+H)) Mass (Theoretical value: 474.57, Measured value: 475 (M + H))
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합성예Synthesis Example
2] 1-2의 합성 2] synthesis of 1-2
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (15.5 g, 45.2 mmol)을 사용하는 것을 제외하고는, 상기 합성예 1과 동일한 과정을 수행하여 목적 화합물인 1-2 (13.6 g, 수율 60%)를 얻었다.2-([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3,5-triazine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using (15.5 g, 45.2 mmol), to obtain the target compound 1-2 (13.6 g, yield 60%) by the same process as in Synthesis Example 1.
Mass (이론치: 550.67, 측정치: 551(M+H))Mass (Theoretical value: 550.67, Measured value: 551 (M + H))
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합성예Synthesis Example
3] 1-3의 합성 3] synthesis of 1-3
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenylpyrimidine (15.5 g, 45.2 mmol)을 사용하는 것을 제외하고는, 상기 합성예 1과 동일한 과정을 수행하여 목적 화합물인 1-3 (13.6 g, 수율 60%)을 얻었다.2-([1,1'-biphenyl] -4-yl) -4-chloro-6-phenylpyrimidine (15.5 g, 45.2 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using the same procedure as in Synthesis Example 1 to obtain the target compound 1-3 (13.6 g, yield 60%).
Mass (이론치: 549.68, 측정치: 550(M+H))Mass (Theoretical value: 549.68, Measured value: 550 (M + H))
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합성예Synthesis Example
4] 1-4의 합성 4] Synthesis of 1-4
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (15.5 g, 45.2 mmol)을 사용하는 것을 제외하고는, 상기 합성예 1과 동일한 과정을 수행하여 목적 화합물인 1-4 (13.6 g, 수율 60%)를 얻었다.The use of 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (15.5 g, 45.2 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except that, the same procedure as in Synthesis Example 1 was carried out to obtain the title compound 1-4 (13.6 g, yield 60%).
Mass (이론치: 550.67, 측정치: 551(M+H))Mass (Theoretical value: 550.67, Measured value: 551 (M + H))
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합성예Synthesis Example
5] 1-5의 합성 5] Synthesis of 1-5
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 4-(3-chlorophenyl)-2,6-diphenylpyrimidine (15.5 g, 45.2 mmol)을 사용하는 것을 제외하고는, 상기 합성예 1과 동일한 과정을 수행하여 목적 화합물인 1-5 (13.6 g, 수율 60%)를 얻었다.Synthesis Example 1 except that 4- (3-chlorophenyl) -2,6-diphenylpyrimidine (15.5 g, 45.2 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine. 1-5 (13.6 g, yield 60%) as a target compound was obtained.
Mass (이론치: 549.68, 측정치: 550(M+H))Mass (Theoretical value: 549.68, Measured value: 550 (M + H))
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합성예Synthesis Example
6] 1-6의 합성 6] Synthesis of 1-6
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine (19.0 g, 45.2 mmol)을 사용하는 것을 제외하고는, 상기 합성예 1과 동일한 과정을 수행하여 목적 화합물인 1-6 (16.0 g, 수율 62%)을 얻었다.2-([1,1'-biphenyl] -4-yl) -4- (3-chlorophenyl) -6-phenyl-1,3 instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using, 5-triazine (19.0 g, 45.2 mmol), the same procedure as in Synthesis Example 1 was carried out to obtain the title compound 1-6 (16.0 g, yield 62%).
Mass (이론치: 626.76, 측정치: 627(M+H))Mass (Theoretical value: 626.76, Measured value: 627 (M + H))
[[
합성예Synthesis Example
7] 1-7의 합성 7] Synthesis of 1-7
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenylpyrimidine (19.0 g, 45.2 mmol)을 사용하는 것을 제외하고는, 상기 합성예 1과 동일한 과정을 수행하여 목적 화합물인 1-7 (16.0 g, 수율 62%)을 얻었다.2-([1,1'-biphenyl] -4-yl) -4- (3-chlorophenyl) -6-phenylpyrimidine (19.0 g, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 45.2 mmol), the same procedure as in Synthesis Example 1 was carried out to obtain the title compound 1-7 (16.0 g, yield 62%).
Mass (이론치: 625.78, 측정치: 626(M+H))Mass (Theoretical value: 625.78, Measured value: 626 (M + H))
[[
합성예Synthesis Example
8] 1-8의 합성 8] Synthesis of 1-8
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine (19.0 g, 45.2 mmol)을 사용하는 것을 제외하고는, 상기 합성예 1과 동일한 과정을 수행하여 목적 화합물인 1-8 (16.0 g, 수율 62%)을 얻었다.2- (3'-chloro- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 5-triazine (19.0 g, 45.2 mmol), the same procedure as in Synthesis Example 1 was performed to obtain 1-8 (16.0 g, yield 62%) as a target compound.
Mass (이론치: 626.76, 측정치: 627(M+H))Mass (Theoretical value: 626.76, Measured value: 627 (M + H))
[[
합성예Synthesis Example
9] 1-9의 합성 9] Synthesis of 1-9
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine (19.0 g, 45.2 mmol)을 사용하는 것을 제외하고는, 상기 합성예 1과 동일한 과정을 수행하여 목적 화합물인 1-9 (16.0 g, 수율 62%)를 얻었다.2- (3'-chloro- [1,1'-biphenyl] -4-yl) -4,6-diphenyl-1,3, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 5-triazine (19.0 g, 45.2 mmol), the same procedure as in Synthesis Example 1 was carried out to obtain the title compound 1-9 (16.0 g, yield 62%).
Mass (이론치: 626.76, 측정치: 627(M+H))Mass (Theoretical value: 626.76, Measured value: 627 (M + H))
[[
합성예Synthesis Example
10] 1-10의 합성 10] Synthesis of 1-10
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(4'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine (19.0 g, 45.2 mmol)을 사용하는 것을 제외하고는, 상기 합성예 1과 동일한 과정을 수행하여 목적 화합물인 1-10 (16.0 g, 수율 62%)을 얻었다.2- (4'-chloro- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 5-triazine (19.0 g, 45.2 mmol), the same procedure as in Synthesis Example 1 was carried out to obtain the title compound 1-10 (16.0 g, 62% yield).
Mass (이론치: 626.76, 측정치: 627(M+H))Mass (Theoretical value: 626.76, Measured value: 627 (M + H))
[[
합성예Synthesis Example
11] 1-11의 합성 11] Synthesis of 1-11
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(4'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine (19.0 g, 45.2 mmol)을 사용하는 것을 제외하고는, 상기 합성예 1과 동일한 과정을 수행하여 목적 화합물인 1-11 (16.0 g, 수율 62%)을 얻었다.2- (4'-chloro- [1,1'-biphenyl] -4-yl) -4,6-diphenyl-1,3, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 5-triazine (19.0 g, 45.2 mmol), to obtain the target compound 1-11 (16.0 g, 62% yield) by the same procedure as in Synthesis Example 1.
Mass (이론치: 626.76, 측정치: 627(M+H))Mass (Theoretical value: 626.76, Measured value: 627 (M + H))
[[
합성예Synthesis Example
12] 1-12의 합성 12] Synthesis of 1-12
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-chloro-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine (16.2 g, 45.2 mmol)을 사용하는 것을 제외하고는, 상기 합성예 1과 동일한 과정을 수행하여 목적 화합물인 1-12 (14.2 g, 수율 61%)를 얻었다.2-chloro-4- (dibenzo [b, d] furan-4-yl) -6-phenyl-1,3,5-triazine (instead of 2-chloro-4,6-diphenyl-1,3,5-triazine) 16.2 g, 45.2 mmol) was obtained in the same manner as in Synthesis Example 1 to obtain 1-12 (14.2 g, yield 61%) of the title compound.
Mass (이론치: 564.65, 측정치: 565(M+H))Mass (Theoretical value: 564.65, Measured value: 565 (M + H))
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합성예Synthesis Example
13] 1-13의 합성 13] Synthesis of 1-13
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (16.2 g, 45.2 mmol)을 사용하는 것을 제외하고는, 상기 합성예 1과 동일한 과정을 수행하여 목적 화합물인 1-13 (14.2 g, 수율 61%)을 얻었다.2-chloro-4- (dibenzo [b, d] furan-3-yl) -6-phenyl-1,3,5-triazine (instead of 2-chloro-4,6-diphenyl-1,3,5-triazine) 16.2 g, 45.2 mmol) was used in the same manner as in Synthesis Example 1 to obtain 1-13 (14.2 g, 61%) of the title compound.
Mass (이론치: 564.65, 측정치: 565(M+H))Mass (Theoretical value: 564.65, Measured value: 565 (M + H))
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합성예Synthesis Example
14] 1-14의 합성 14] Synthesis of 1-14
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-chloro-4-(dibenzo[b,d]furan-2-yl)-6-phenyl-1,3,5-triazine (16.2 g, 45.2 mmol)을 사용하는 것을 제외하고는, 상기 합성예 1과 동일한 과정을 수행하여 목적 화합물인 1-14 (14.2 g, 수율 61%)를 얻었다.2-chloro-4- (dibenzo [b, d] furan-2-yl) -6-phenyl-1,3,5-triazine (instead of 2-chloro-4,6-diphenyl-1,3,5-triazine) 16.2 g, 45.2 mmol) was used in the same manner as in Synthesis Example 1 to obtain 1-14 (14.2 g, yield 61%) as a target compound.
Mass (이론치: 564.65, 측정치: 565(M+H))Mass (Theoretical value: 564.65, Measured value: 565 (M + H))
[[
합성예Synthesis Example
15] 1-15의 합성 15] Synthesis of 1-15
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-chloro-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine (16.2 g, 45.2 mmol)을 사용하는 것을 제외하고는, 상기 합성예 1과 동일한 과정을 수행하여 목적 화합물인 1-15 (14.2 g, 수율 61%)를 얻었다.2-chloro-4- (dibenzo [b, d] furan-1-yl) -6-phenyl-1,3,5-triazine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine ( 16.2 g, 45.2 mmol) was used in the same manner as in Synthesis Example 1 to obtain 1-15 (14.2 g, 61%) of the title compound.
Mass (이론치: 564.65, 측정치: 565(M+H))Mass (Theoretical value: 564.65, Measured value: 565 (M + H))
[[
합성예Synthesis Example
16] 1-16의 합성 16] Synthesis of 1-16
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3-chlorophenyl)-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine (19.6 g, 45.2 mmol)을 사용하는 것을 제외하고는, 상기 합성예 1과 동일한 과정을 수행하여 목적 화합물인 1-16 (15.3 g, 수율 58%)을 얻었다.2- (3-chlorophenyl) -4- (dibenzo [b, d] furan-4-yl) -6-phenyl-1,3, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 5-triazine (19.6 g, 45.2 mmol), the same procedure as in Synthesis Example 1 was carried out to obtain the title compound 1-16 (15.3 g, yield 58%).
Mass (이론치: 640.75, 측정치: 641(M+H))Mass (Theoretical value: 640.75, Measured value: 641 (M + H))
[[
합성예Synthesis Example
17] 1-17의 합성 17] Synthesis of 1-17
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3-chlorophenyl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (19.6 g, 45.2 mmol)을 사용하는 것을 제외하고는, 상기 합성예 1과 동일한 과정을 수행하여 목적 화합물인 1-17 (15.3 g, 수율 58%)을 얻었다.2- (3-chlorophenyl) -4- (dibenzo [b, d] furan-3-yl) -6-phenyl-1,3, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 5-triazine (19.6 g, 45.2 mmol), the same procedure as in Synthesis Example 1 was carried out to obtain the title compound 1-17 (15.3 g, yield 58%).
Mass (이론치: 640.75, 측정치: 641(M+H))Mass (Theoretical value: 640.75, Measured value: 641 (M + H))
[[
합성예Synthesis Example
18] 1-18의 합성 18] Synthesis of 1-18
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3-chlorophenyl)-4-(dibenzo[b,d]furan-2-yl)-6-phenyl-1,3,5-triazine (19.6 g, 45.2 mmol)을 사용하는 것을 제외하고는, 상기 합성예 1과 동일한 과정을 수행하여 목적 화합물인 1-18 (15.3 g, 수율 58%)을 얻었다.2- (3-chlorophenyl) -4- (dibenzo [b, d] furan-2-yl) -6-phenyl-1,3, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 5-triazine (19.6 g, 45.2 mmol), the same procedure as in Synthesis Example 1 was carried out to obtain the title compound 1-18 (15.3 g, yield 58%).
Mass (이론치: 640.75, 측정치: 641(M+H))Mass (Theoretical value: 640.75, Measured value: 641 (M + H))
[[
합성예Synthesis Example
19] 1-19의 합성 19] Synthesis of 1-19
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3-chlorophenyl)-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine (19.6 g, 45.2 mmol)을 사용하는 것을 제외하고는, 상기 합성예 1과 동일한 과정을 수행하여 목적 화합물인 1-19 (15.3 g, 수율 58%)를 얻었다.2- (3-chlorophenyl) -4- (dibenzo [b, d] furan-1-yl) -6-phenyl-1,3, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 5-triazine (19.6 g, 45.2 mmol), the same procedure as in Synthesis Example 1 was carried out to obtain the title compound 1-19 (15.3 g, yield 58%).
Mass (이론치: 640.75, 측정치: 641(M+H))Mass (Theoretical value: 640.75, Measured value: 641 (M + H))
[[
합성예Synthesis Example
20] 1-20의 합성 20] Synthesis of 1-20
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine (23.1 g, 45.2 mmol)을 사용하는 것을 제외하고는, 상기 합성예 1과 동일한 과정을 수행하여 목적 화합물인 1-20 (16.2 g, 수율 55%)을 얻었다.2- (3'-chloro- [1,1'-biphenyl] -3-yl) -4- (dibenzo [b, d] furan instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 4-yl) -6-phenyl-1,3,5-triazine (23.1 g, 45.2 mmol), the same procedure as in Synthesis Example 1 was carried out to give the target compound 1-20 (16.2). g, yield 55%) was obtained.
Mass (이론치: 716.84, 측정치: 717(M+H))Mass (Theoretical value: 716.84, Measured value: 717 (M + H))
[[
합성예Synthesis Example
21] 1-21의 합성 21] Synthesis of 1-21
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (23.1 g, 45.2 mmol)을 사용하는 것을 제외하고는, 상기 합성예 1과 동일한 과정을 수행하여 목적 화합물인 1-21 (16.2 g, 수율 55%)을 얻었다.2- (3'-chloro- [1,1'-biphenyl] -3-yl) -4- (dibenzo [b, d] furan instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using -3-yl) -6-phenyl-1,3,5-triazine (23.1 g, 45.2 mmol), the same procedure as in Synthesis Example 1 was carried out to obtain the title compound 1-21 (16.2). g, yield 55%) was obtained.
Mass (이론치: 716.84, 측정치: 717(M+H))Mass (Theoretical value: 716.84, Measured value: 717 (M + H))
[[
합성예Synthesis Example
22] 1-22의 합성 22] Synthesis of 1-22
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4-(dibenzo[b,d]furan-2-yl)-6-phenyl-1,3,5-triazine (23.1 g, 45.2 mmol)을 사용하는 것을 제외하고는, 상기 합성예 1과 동일한 과정을 수행하여 목적 화합물인 1-22 (16.2 g, 수율 55%)를 얻었다.2- (3'-chloro- [1,1'-biphenyl] -3-yl) -4- (dibenzo [b, d] furan instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 2--2-yl) -6-phenyl-1,3,5-triazine (23.1 g, 45.2 mmol), the same procedure as in Synthesis Example 1 was carried out to obtain the title compound 1-22 (16.2). g, yield 55%) was obtained.
Mass (이론치: 716.84, 측정치: 717(M+H))Mass (Theoretical value: 716.84, Measured value: 717 (M + H))
[[
합성예Synthesis Example
23] 1-23의 합성 23] Synthesis of 1-23
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine (23.1 g, 45.2 mmol)을 사용하는 것을 제외하고는, 상기 합성예 1과 동일한 과정을 수행하여 목적 화합물인 1-23 (16.2 g, 수율 55%)을 얻었다.2- (3'-chloro- [1,1'-biphenyl] -3-yl) -4- (dibenzo [b, d] furan instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using -1-yl) -6-phenyl-1,3,5-triazine (23.1 g, 45.2 mmol), the same procedure as in Synthesis Example 1 was carried out to obtain the title compound 1-23 (16.2). g, yield 55%) was obtained.
Mass (이론치: 716.84, 측정치: 717(M+H))Mass (Theoretical value: 716.84, Measured value: 717 (M + H))
[[
합성예Synthesis Example
24] 2-1의 합성 24] Synthesis of 2-1
질소 기류 하에서 Core-2 (10 g, 31.3 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (9.22 g, 34.4 mmol), CuI (0.596 g, 3.13 mmol), 1,10-phenanthroline (1.13 g, 6.26 mmol), Cs2CO3 (20.4 g, 62.6 mmol) 및 nitrobenzene (100 ml)를 혼합하고 210℃ 에서 3시간 동안 교반하였다. 반응이 종결된 후 고체염을 필터링한 후, 컬럼 크로마토그래피로 정제하여 목적 화합물인 2-1 (10.7 g, 수율 62%)을 얻었다.Core-2 (10 g, 31.3 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (9.22 g, 34.4 mmol), CuI (0.596 g, 3.13 mmol), 1, under a nitrogen stream. 10-phenanthroline (1.13 g, 6.26 mmol), Cs 2 CO 3 (20.4 g, 62.6 mmol) and nitrobenzene (100 ml) were mixed and stirred at 210 ° C. for 3 hours. After the reaction was terminated, the solid salt was filtered and purified by column chromatography to obtain the title compound 2-1 (10.7 g, yield 62%).
Mass (이론치: 550.67, 측정치: 551(M+H)) Mass (Theoretical value: 550.67, Measured value: 551 (M + H))
[[
합성예Synthesis Example
25] 2-2의 합성 25] Synthesis of 2-2
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (11.3 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 24와 동일한 과정을 수행하여 목적 화합물인 2-2 (12.6 g, 수율 64%)를 얻었다.2-([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3,5-triazine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using (11.3 g, 34.4 mmol), to obtain the target compound 2-2 (12.6 g, yield 64%) by the same procedure as in Synthesis Example 24.
Mass (이론치: 626.76, 측정치: 627(M+H))Mass (Theoretical value: 626.76, Measured value: 627 (M + H))
[[
합성예Synthesis Example
26] 2-3의 합성 26] synthesis of 2-3
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenylpyrimidine (11.3 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 24와 동일한 과정을 수행하여 목적 화합물인 2-3 (12.6 g, 수율 64%)을 얻었다.2-([1,1'-biphenyl] -4-yl) -4-chloro-6-phenylpyrimidine (11.3 g, 34.4 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using the same procedure as in Synthesis Example 24, the target compound 2-3 (12.6 g, yield 64%) was obtained.
Mass (이론치: 625.78, 측정치: 626(M+H))Mass (Theoretical value: 625.78, Measured value: 626 (M + H))
[[
합성예Synthesis Example
27] 2-4의 합성 27] Synthesis of 2-4
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (11.3 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 24와 동일한 과정을 수행하여 목적 화합물인 2-4 (12.6 g, 수율 64%)를 얻었다.Use of 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (11.3 g, 34.4 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except that, the same procedure as in Synthesis Example 24 was carried out to obtain 2-4 (12.6 g, yield 64%) of the title compound.
Mass (이론치: 626.76, 측정치: 627(M+H))Mass (Theoretical value: 626.76, Measured value: 627 (M + H))
[[
합성예Synthesis Example
28] 2-5의 합성 28] Synthesis of 2-5
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 4-(3-chlorophenyl)-2,6-diphenylpyrimidine (11.3 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 24와 동일한 과정을 수행하여 목적 화합물인 2-5 (12.6 g, 수율 64%)를 얻었다.Synthesis Example 24 except that 4- (3-chlorophenyl) -2,6-diphenylpyrimidine (11.3 g, 34.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine 2-5 (12.6 g, yield 64%) as a target compound was obtained by the same process as the above.
Mass (이론치: 625.78, 측정치: 626(M+H))Mass (Theoretical value: 625.78, Measured value: 626 (M + H))
[[
합성예Synthesis Example
29] 2-6의 합성 29] Synthesis of 2-6
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine (14.5 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 24와 동일한 과정을 수행하여 목적 화합물인 2-6 (13.2 g, 수율 60%)을 얻었다.2-([1,1'-biphenyl] -4-yl) -4- (3-chlorophenyl) -6-phenyl-1,3 instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using, 5-triazine (14.5 g, 34.4 mmol), to obtain the target compound 2-6 (13.2 g, yield 60%) was carried out in the same manner as in Synthesis Example 24.
Mass (이론치: 702.86, 측정치: 703(M+H))Mass (Theoretical value: 702.86, Measured value: 703 (M + H))
[[
합성예Synthesis Example
30] 2-7의 합성 30] Synthesis of 2-7
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenylpyrimidine (14.5 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 24와 동일한 과정을 수행하여 목적 화합물인 2-7 (13.2 g, 수율 60%)을 얻었다.2-([1,1'-biphenyl] -4-yl) -4- (3-chlorophenyl) -6-phenylpyrimidine (14.5 g, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 34.4 mmol), the same procedure as in Synthesis Example 24 was carried out to obtain 2-7 (13.2 g, yield 60%) of the title compound.
Mass (이론치: 701.87, 측정치: 702(M+H))Mass (Theoretical value: 701.87, Measured value: 702 (M + H))
[[
합성예Synthesis Example
31] 2-8의 합성 31] Synthesis of 2-8
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine (14.5 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 24와 동일한 과정을 수행하여 목적 화합물인 2-8 (13.2 g, 수율 60%)을 얻었다.2- (3'-chloro- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 5-triazine (14.5 g, 34.4 mmol), to obtain the target compound 2-8 (13.2 g, yield 60%) by the same procedure as in Synthesis Example 24.
Mass (이론치: 702.86, 측정치: 703(M+H))Mass (Theoretical value: 702.86, Measured value: 703 (M + H))
[[
합성예Synthesis Example
32] 2-9의 합성 32] Synthesis of 2-9
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine (14.5 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 24와 동일한 과정을 수행하여 목적 화합물인 2-9 (13.2 g, 수율 60%)를 얻었다.2- (3'-chloro- [1,1'-biphenyl] -4-yl) -4,6-diphenyl-1,3, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 5-triazine (14.5 g, 34.4 mmol), to obtain the target compound 2-9 (13.2 g, yield 60%) was carried out in the same manner as in Synthesis Example 24.
Mass (이론치: 702.86, 측정치: 703(M+H))Mass (Theoretical value: 702.86, Measured value: 703 (M + H))
[[
합성예Synthesis Example
33] 2-10의 합성 33] Synthesis of 2-10
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(4'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine (14.5 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 24와 동일한 과정을 수행하여 목적 화합물인 2-10 (13.2 g, 수율 60%)을 얻었다.2- (4'-chloro- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 5-triazine (14.5 g, 34.4 mmol), the same procedure as in Synthesis Example 24 was carried out to obtain 2-10 (13.2 g, yield 60%) as a target compound.
Mass (이론치: 702.86, 측정치: 703(M+H))Mass (Theoretical value: 702.86, Measured value: 703 (M + H))
[[
합성예Synthesis Example
34] 2-11의 합성 34] Synthesis of 2-11
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(4'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine (14.5 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 24와 동일한 과정을 수행하여 목적 화합물인 2-11 (13.2 g, 수율 60%)을 얻었다.2- (4'-chloro- [1,1'-biphenyl] -4-yl) -4,6-diphenyl-1,3, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 5-triazine (14.5 g, 34.4 mmol), the same procedure as in Synthesis Example 24 was carried out to obtain the title compound 2-11 (13.2 g, yield 60%).
Mass (이론치: 702.86, 측정치: 703(M+H))Mass (Theoretical value: 702.86, Measured value: 703 (M + H))
[[
합성예Synthesis Example
35] 2-12의 합성 35] Synthesis of 2-12
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-chloro-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine (12.3 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 24와 동일한 과정을 수행하여 목적 화합물인 2-12 (11.0 g, 수율 55%)를 얻었다.2-chloro-4- (dibenzo [b, d] furan-4-yl) -6-phenyl-1,3,5-triazine (instead of 2-chloro-4,6-diphenyl-1,3,5-triazine) 12.3 g, 34.4 mmol) was obtained in the same manner as in Synthesis Example 24, to obtain 2-12 (11.0 g, yield 55%) of the title compound.
Mass (이론치: 640.75, 측정치: 641(M+H))Mass (Theoretical value: 640.75, Measured value: 641 (M + H))
[[
합성예Synthesis Example
36] 2-13의 합성 36] Synthesis of 2-13
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (12.3 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 24와 동일한 과정을 수행하여 목적 화합물인 2-13 (11.0 g, 수율 55%)을 얻었다.2-chloro-4- (dibenzo [b, d] furan-3-yl) -6-phenyl-1,3,5-triazine (instead of 2-chloro-4,6-diphenyl-1,3,5-triazine) 12.3 g, 34.4 mmol) was obtained in the same manner as in Synthesis Example 24, to obtain 2-13 (11.0 g, 55% yield) of the title compound.
Mass (이론치: 640.75, 측정치: 641(M+H))Mass (Theoretical value: 640.75, Measured value: 641 (M + H))
[[
합성예Synthesis Example
37] 2-14의 합성 37] Synthesis of 2-14
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-chloro-4-(dibenzo[b,d]furan-2-yl)-6-phenyl-1,3,5-triazine (12.3 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 24와 동일한 과정을 수행하여 목적 화합물인 2-14 (11.0 g, 수율 55%)를 얻었다.2-chloro-4- (dibenzo [b, d] furan-2-yl) -6-phenyl-1,3,5-triazine (instead of 2-chloro-4,6-diphenyl-1,3,5-triazine) Except for using 12.3 g, 34.4 mmol), to obtain the target compound 2-14 (11.0 g, 55% yield) by the same process as in Synthesis Example 24.
Mass (이론치: 640.75, 측정치: 641(M+H))Mass (Theoretical value: 640.75, Measured value: 641 (M + H))
[[
합성예Synthesis Example
38] 2-15의 합성 38] Synthesis of 2-15
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-chloro-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine (12.3 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 24와 동일한 과정을 수행하여 목적 화합물인 2-15 (11.0 g, 수율 55%)를 얻었다.2-chloro-4- (dibenzo [b, d] furan-1-yl) -6-phenyl-1,3,5-triazine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine ( Except for using 12.3 g, 34.4 mmol), to obtain the target compound 2-15 (11.0 g, yield 55%) was carried out in the same manner as in Synthesis Example 24.
Mass (이론치: 640.75, 측정치: 641(M+H))Mass (Theoretical value: 640.75, Measured value: 641 (M + H))
[[
합성예Synthesis Example
39] 2-16의 합성 39] Synthesis of 2-16
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3-chlorophenyl)-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine (14.9 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 24와 동일한 과정을 수행하여 목적 화합물인 2-16 (13.0 g, 수율 58%)을 얻었다.2- (3-chlorophenyl) -4- (dibenzo [b, d] furan-4-yl) -6-phenyl-1,3, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 5-triazine (14.9 g, 34.4 mmol), the same procedure as in Synthesis Example 24 was carried out to obtain the title compound 2-16 (13.0 g, yield 58%).
Mass (이론치: 716.84, 측정치: 717(M+H))Mass (Theoretical value: 716.84, Measured value: 717 (M + H))
[[
합성예Synthesis Example
40] 2-17의 합성 40] Synthesis of 2-17
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3-chlorophenyl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (14.9 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 24와 동일한 과정을 수행하여 목적 화합물인 2-17 (13.0 g, 수율 58%)을 얻었다.2- (3-chlorophenyl) -4- (dibenzo [b, d] furan-3-yl) -6-phenyl-1,3, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 5-triazine (14.9 g, 34.4 mmol), the same procedure as in Synthesis Example 24 was carried out to obtain 2-17 (13.0 g, yield 58%) as a target compound.
Mass (이론치: 716.84, 측정치: 717(M+H))Mass (Theoretical value: 716.84, Measured value: 717 (M + H))
[[
합성예Synthesis Example
41] 2-18의 합성 41] Synthesis of 2-18
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3-chlorophenyl)-4-(dibenzo[b,d]furan-2-yl)-6-phenyl-1,3,5-triazine (14.9 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 24와 동일한 과정을 수행하여 목적 화합물인 2-18 (13.0 g, 수율 58%)을 얻었다.2- (3-chlorophenyl) -4- (dibenzo [b, d] furan-2-yl) -6-phenyl-1,3, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 5-triazine (14.9 g, 34.4 mmol), the same procedure as in Synthesis Example 24 was carried out to obtain the title compound 2-18 (13.0 g, yield 58%).
Mass (이론치: 716.84, 측정치: 717(M+H))Mass (Theoretical value: 716.84, Measured value: 717 (M + H))
[[
합성예Synthesis Example
42] 2-19의 합성 42] Synthesis of 2-19
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3-chlorophenyl)-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine (14.9 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 24와 동일한 과정을 수행하여 목적 화합물인 2-19 (13.0 g, 수율 58%)를 얻었다.2- (3-chlorophenyl) -4- (dibenzo [b, d] furan-1-yl) -6-phenyl-1,3, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 5-triazine (14.9 g, 34.4 mmol), the same procedure as in Synthesis Example 24 was carried out to obtain the title compound 2-19 (13.0 g, yield 58%).
Mass (이론치: 716.84, 측정치: 717(M+H))Mass (Theoretical value: 716.84, Measured value: 717 (M + H))
[[
합성예Synthesis Example
43] 2-20의 합성 43] Synthesis of 2-20
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine (17.6 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 24와 동일한 과정을 수행하여 목적 화합물인 2-20 (13.2 g, 수율 53%)을 얻었다.2- (3'-chloro- [1,1'-biphenyl] -3-yl) -4- (dibenzo [b, d] furan instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 4-yl) -6-phenyl-1,3,5-triazine (17.6 g, 34.4 mmol), the same procedure as in Synthesis Example 24 was carried out to obtain the target compound 2-20 (13.2). g, yield 53%).
Mass (이론치: 792.94, 측정치: 793(M+H))Mass (Theoretical value: 792.94, Measured value: 793 (M + H))
[[
합성예Synthesis Example
44] 2-21의 합성 44] Synthesis of 2-21
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (17.6 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 24와 동일한 과정을 수행하여 목적 화합물인 2-21 (13.2 g, 수율 53%)을 얻었다.2- (3'-chloro- [1,1'-biphenyl] -3-yl) -4- (dibenzo [b, d] furan instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using -3-yl) -6-phenyl-1,3,5-triazine (17.6 g, 34.4 mmol), the same procedure as in Synthesis Example 24 was carried out to provide 2-21 (13.2) as a target compound. g, yield 53%).
Mass (이론치: 792.94, 측정치: 793(M+H))Mass (Theoretical value: 792.94, Measured value: 793 (M + H))
[[
합성예Synthesis Example
45] 2-22의 합성 45] Synthesis of 2-22
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4-(dibenzo[b,d]furan-2-yl)-6-phenyl-1,3,5-triazine (17.6 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 24와 동일한 과정을 수행하여 목적 화합물인 2-22 (13.2 g, 수율 53%)를 얻었다.2- (3'-chloro- [1,1'-biphenyl] -3-yl) -4- (dibenzo [b, d] furan instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 2-yl) -6-phenyl-1,3,5-triazine (17.6 g, 34.4 mmol), the same procedure as in Synthesis Example 24 was carried out to provide 2-22 (13.2) as a target compound. g, yield 53%).
Mass (이론치: 792.94, 측정치: 793(M+H))Mass (Theoretical value: 792.94, Measured value: 793 (M + H))
[[
합성예Synthesis Example
46] 2-23의 합성 46] Synthesis of 2-23
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine (17.6 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 24와 동일한 과정을 수행하여 목적 화합물인 2-23 (13.2 g, 수율 53%)을 얻었다.2- (3'-chloro- [1,1'-biphenyl] -3-yl) -4- (dibenzo [b, d] furan instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using -1-yl) -6-phenyl-1,3,5-triazine (17.6 g, 34.4 mmol), the same procedure as in Synthesis Example 24 was carried out to provide 2-23 (13.2) as a target compound. g, yield 53%).
Mass (이론치: 792.94, 측정치: 793(M+H))Mass (Theoretical value: 792.94, Measured value: 793 (M + H))
[[
합성예Synthesis Example
47] 3-1의 합성 47] Synthesis of 3-1
질소 기류 하에서 Core-3 (10 g, 31.3 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (9.22 g, 34.4 mmol), CuI (0.596 g, 3.13 mmol), 1,10-phenanthroline (1.13 g, 6.26 mmol), Cs2CO3 (20.4 g, 62.6 mmol) 및 nitrobenzene (100 ml)를 혼합하고 210℃ 에서 3시간 동안 교반하였다. 반응이 종결된 후 고체염을 필터링한 후, 컬럼 크로마토그래피로 정제하여 목적 화합물인 3-1 (10.7 g, 수율 62%)을 얻었다.Core-3 (10 g, 31.3 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (9.22 g, 34.4 mmol), CuI (0.596 g, 3.13 mmol), 1, under a nitrogen stream. 10-phenanthroline (1.13 g, 6.26 mmol), Cs 2 CO 3 (20.4 g, 62.6 mmol) and nitrobenzene (100 ml) were mixed and stirred at 210 ° C. for 3 hours. After the reaction was completed, the solid salt was filtered and purified by column chromatography to obtain the title compound 3-1 (10.7 g, 62% yield).
Mass (이론치: 550.67, 측정치: 551(M+H)) Mass (Theoretical value: 550.67, Measured value: 551 (M + H))
[[
합성예Synthesis Example
48] 3-2의 합성 48] Synthesis of 3-2
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (11.3 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 47과 동일한 과정을 수행하여 목적 화합물인 3-2 (12.6 g, 수율 64%)를 얻었다.2-([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3,5-triazine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using (11.3 g, 34.4 mmol), to obtain the target compound 3-2 (12.6 g, 64% yield) by the same procedure as in Synthesis Example 47.
Mass (이론치: 626.76, 측정치: 627(M+H))Mass (Theoretical value: 626.76, Measured value: 627 (M + H))
[[
합성예Synthesis Example
49] 3-3의 합성 49] Synthesis of 3-3
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenylpyrimidine (11.3 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 47과 동일한 과정을 수행하여 목적 화합물인 3-3 (12.6 g, 수율 64%)을 얻었다.2-([1,1'-biphenyl] -4-yl) -4-chloro-6-phenylpyrimidine (11.3 g, 34.4 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using the same procedure as in Synthesis Example 47, the title compound 3-3 (12.6 g, yield 64%) was obtained.
Mass (이론치: 625.78, 측정치: 626(M+H))Mass (Theoretical value: 625.78, Measured value: 626 (M + H))
[[
합성예Synthesis Example
50] 3-4의 합성 50] Synthesis of 3-4
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (11.3 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 47과 동일한 과정을 수행하여 목적 화합물인 3-4 (12.6 g, 수율 64%)를 얻었다.Use of 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (11.3 g, 34.4 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except that, the same procedure as in Synthesis Example 47 was carried out to obtain the title compound 3-4 (12.6 g, yield 64%).
Mass (이론치: 626.76, 측정치: 627(M+H))Mass (Theoretical value: 626.76, Measured value: 627 (M + H))
[[
합성예Synthesis Example
51] 3-5의 합성 51] Synthesis of 3-5
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 4-(3-chlorophenyl)-2,6-diphenylpyrimidine (11.3 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 47과 동일한 과정을 수행하여 목적 화합물인 3-5 (12.6 g, 수율 64%)를 얻었다.Synthesis Example 47 except that 4- (3-chlorophenyl) -2,6-diphenylpyrimidine (11.3 g, 34.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine. By the same process as in the title compound to obtain 3-5 (12.6 g, 64% yield).
Mass (이론치: 625.78, 측정치: 626(M+H))Mass (Theoretical value: 625.78, Measured value: 626 (M + H))
[[
합성예Synthesis Example
52] 3-6의 합성 52] Synthesis of 3-6
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine (14.5 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 47과 동일한 과정을 수행하여 목적 화합물인 3-6 (13.2 g, 수율 60%)을 얻었다.2-([1,1'-biphenyl] -4-yl) -4- (3-chlorophenyl) -6-phenyl-1,3 instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using, 5-triazine (14.5 g, 34.4 mmol), to obtain the target compound 3-6 (13.2 g, yield 60%) was carried out in the same manner as in Synthesis Example 47.
Mass (이론치: 702.86, 측정치: 703(M+H))Mass (Theoretical value: 702.86, Measured value: 703 (M + H))
[[
합성예Synthesis Example
53] 3-7의 합성 53] Synthesis of 3-7
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenylpyrimidine (14.5 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 47과 동일한 과정을 수행하여 목적 화합물인 3-7 (13.2 g, 수율 60%)을 얻었다.2-([1,1'-biphenyl] -4-yl) -4- (3-chlorophenyl) -6-phenylpyrimidine (14.5 g, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 34.4 mmol), the same procedure as in Synthesis Example 47 was carried out to obtain 3-7 (13.2 g, yield 60%) of the title compound.
Mass (이론치: 701.87, 측정치: 702(M+H))Mass (Theoretical value: 701.87, Measured value: 702 (M + H))
[[
합성예Synthesis Example
54] 3-8의 합성 54] Synthesis of 3-8
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine (14.5 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 47과 동일한 과정을 수행하여 목적 화합물인 3-8 (13.2 g, 수율 60%)을 얻었다.2- (3'-chloro- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 5-triazine (14.5 g, 34.4 mmol), to obtain the target compound 3-8 (13.2 g, yield 60%) was carried out in the same manner as in Synthesis Example 47.
Mass (이론치: 702.86, 측정치: 703(M+H))Mass (Theoretical value: 702.86, Measured value: 703 (M + H))
[[
합성예Synthesis Example
55] 3-9의 합성 55] Synthesis of 3-9
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine (14.5 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 47과 동일한 과정을 수행하여 목적 화합물인 3-9 (13.2 g, 수율 60%)를 얻었다.2- (3'-chloro- [1,1'-biphenyl] -4-yl) -4,6-diphenyl-1,3, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 5-triazine (14.5 g, 34.4 mmol), to obtain the target compound 3-9 (13.2 g, yield 60%) in the same manner as in Synthesis Example 47.
Mass (이론치: 702.86, 측정치: 703(M+H))Mass (Theoretical value: 702.86, Measured value: 703 (M + H))
[[
합성예Synthesis Example
56] 3-10의 합성 56] Synthesis of 3-10
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(4'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine (14.5 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 47과 동일한 과정을 수행하여 목적 화합물인 3-10 (13.2 g, 수율 60%)을 얻었다.2- (4'-chloro- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 5-triazine (14.5 g, 34.4 mmol), to obtain the target compound 3-10 (13.2 g, yield 60%) was carried out in the same manner as in Synthesis Example 47.
Mass (이론치: 702.86, 측정치: 703(M+H))Mass (Theoretical value: 702.86, Measured value: 703 (M + H))
[[
합성예Synthesis Example
57] 3-11의 합성 57] Synthesis of 3-11
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(4'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine (14.5 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 47과 동일한 과정을 수행하여 목적 화합물인 3-11 (13.2 g, 수율 60%)을 얻었다.2- (4'-chloro- [1,1'-biphenyl] -4-yl) -4,6-diphenyl-1,3, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 5-triazine (14.5 g, 34.4 mmol), to obtain the target compound 3-11 (13.2 g, yield 60%) was carried out in the same manner as in Synthesis Example 47.
Mass (이론치: 702.86, 측정치: 703(M+H))Mass (Theoretical value: 702.86, Measured value: 703 (M + H))
[[
합성예Synthesis Example
58] 3-12의 합성 58] Synthesis of 3-12
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-chloro-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine (12.3 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 47과 동일한 과정을 수행하여 목적 화합물인 3-12 (11.0 g, 수율 55%)를 얻었다.2-chloro-4- (dibenzo [b, d] furan-4-yl) -6-phenyl-1,3,5-triazine (instead of 2-chloro-4,6-diphenyl-1,3,5-triazine) 12.3 g, 34.4 mmol) was obtained in the same manner as in Synthesis Example 47 to obtain 3-12 (11.0 g, yield 55%) of the title compound.
Mass (이론치: 640.75, 측정치: 641(M+H))Mass (Theoretical value: 640.75, Measured value: 641 (M + H))
[[
합성예Synthesis Example
59] 3-13의 합성 59] Synthesis of 3-13
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (12.3 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 47과 동일한 과정을 수행하여 목적 화합물인 3-13 (11.0 g, 수율 55%)을 얻었다.2-chloro-4- (dibenzo [b, d] furan-3-yl) -6-phenyl-1,3,5-triazine (instead of 2-chloro-4,6-diphenyl-1,3,5-triazine) 12.3 g, 34.4 mmol) was obtained, and the same procedure as in Synthesis Example 47 was performed, to obtain 3-13 (11.0 g, 55% yield) of the title compound.
Mass (이론치: 640.75, 측정치: 641(M+H))Mass (Theoretical value: 640.75, Measured value: 641 (M + H))
[[
합성예Synthesis Example
60] 3-14의 합성 60] Synthesis of 3-14
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-chloro-4-(dibenzo[b,d]furan-2-yl)-6-phenyl-1,3,5-triazine (12.3 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 47과 동일한 과정을 수행하여 목적 화합물인 3-14 (11.0 g, 수율 55%)를 얻었다.2-chloro-4- (dibenzo [b, d] furan-2-yl) -6-phenyl-1,3,5-triazine (instead of 2-chloro-4,6-diphenyl-1,3,5-triazine) 12.3 g, 34.4 mmol) was obtained, and the same procedure as in Synthesis Example 47 was performed, to obtain 3-14 (11.0 g, 55% yield) of the title compound.
Mass (이론치: 640.75, 측정치: 641(M+H))Mass (Theoretical value: 640.75, Measured value: 641 (M + H))
[[
합성예Synthesis Example
61] 3-15의 합성 61] Synthesis Of 3-15
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-chloro-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine (12.3 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 47과 동일한 과정을 수행하여 목적 화합물인 3-15 (11.0 g, 수율 55%)를 얻었다.2-chloro-4- (dibenzo [b, d] furan-1-yl) -6-phenyl-1,3,5-triazine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine ( Except for using 12.3 g, 34.4 mmol), to obtain the target compound 3-15 (11.0 g, 55% yield) by the same process as in Synthesis Example 47.
Mass (이론치: 640.75, 측정치: 641(M+H))Mass (Theoretical value: 640.75, Measured value: 641 (M + H))
[[
합성예Synthesis Example
62] 3-16의 합성 62] Synthesis Of 3-16
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3-chlorophenyl)-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine (14.9 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 47과 동일한 과정을 수행하여 목적 화합물인 3-16 (13.0 g, 수율 58%)을 얻었다.2- (3-chlorophenyl) -4- (dibenzo [b, d] furan-4-yl) -6-phenyl-1,3, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 5-triazine (14.9 g, 34.4 mmol), to obtain the target compound 3-16 (13.0 g, 58% yield) by the same procedure as in Synthesis Example 47.
Mass (이론치: 716.84, 측정치: 717(M+H))Mass (Theoretical value: 716.84, Measured value: 717 (M + H))
[[
합성예Synthesis Example
63] 3-17의 합성 63] Synthesis of 3-17
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3-chlorophenyl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (14.9 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 47과 동일한 과정을 수행하여 목적 화합물인 3-17 (13.0 g, 수율 58%)을 얻었다.2- (3-chlorophenyl) -4- (dibenzo [b, d] furan-3-yl) -6-phenyl-1,3, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 5-triazine (14.9 g, 34.4 mmol), the same procedure as in Synthesis Example 47 was carried out to obtain 3-17 (13.0 g, yield 58%) as a target compound.
Mass (이론치: 716.84, 측정치: 717(M+H))Mass (Theoretical value: 716.84, Measured value: 717 (M + H))
[[
합성예Synthesis Example
64] 3-18의 합성 64] Synthesis Of 3-18
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3-chlorophenyl)-4-(dibenzo[b,d]furan-2-yl)-6-phenyl-1,3,5-triazine (14.9 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 47과 동일한 과정을 수행하여 목적 화합물인 3-18 (13.0 g, 수율 58%)을 얻었다.2- (3-chlorophenyl) -4- (dibenzo [b, d] furan-2-yl) -6-phenyl-1,3, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 5-triazine (14.9 g, 34.4 mmol), the same procedure as in Synthesis Example 47 was carried out to obtain the title compound 3-18 (13.0 g, yield 58%).
Mass (이론치: 716.84, 측정치: 717(M+H))Mass (Theoretical value: 716.84, Measured value: 717 (M + H))
[[
합성예Synthesis Example
65] 3-19의 합성 65] Synthesis of 3-19
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3-chlorophenyl)-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine (14.9 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 47과 동일한 과정을 수행하여 목적 화합물인 3-19 (13.0 g, 수율 58%)를 얻었다.2- (3-chlorophenyl) -4- (dibenzo [b, d] furan-1-yl) -6-phenyl-1,3, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 5-triazine (14.9 g, 34.4 mmol), the same procedure as in Synthesis Example 47 was carried out to obtain 3-19 (13.0 g, yield 58%) as a target compound.
Mass (이론치: 716.84, 측정치: 717(M+H))Mass (Theoretical value: 716.84, Measured value: 717 (M + H))
[[
합성예Synthesis Example
66] 3-20의 합성 66] Synthesis Of 3-20
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine (17.6 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 47과 동일한 과정을 수행하여 목적 화합물인 3-20 (13.2 g, 수율 53%)을 얻었다.2- (3'-chloro- [1,1'-biphenyl] -3-yl) -4- (dibenzo [b, d] furan instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 4-yl) -6-phenyl-1,3,5-triazine (17.6 g, 34.4 mmol), the same procedure as in Synthesis Example 47 was carried out to obtain 3-20 (13.2) as a target compound. g, yield 53%).
Mass (이론치: 792.94, 측정치: 793(M+H))Mass (Theoretical value: 792.94, Measured value: 793 (M + H))
[[
합성예Synthesis Example
67] 3-21의 합성 67] Synthesis of 3-21
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (17.6 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 47과 동일한 과정을 수행하여 목적 화합물인 3-21 (13.2 g, 수율 53%)을 얻었다.2- (3'-chloro- [1,1'-biphenyl] -3-yl) -4- (dibenzo [b, d] furan instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using -3-yl) -6-phenyl-1,3,5-triazine (17.6 g, 34.4 mmol), the same procedure as in Synthesis Example 47 was carried out to provide 3-21 (13.2) as a target compound. g, yield 53%).
Mass (이론치: 792.94, 측정치: 793(M+H))Mass (Theoretical value: 792.94, Measured value: 793 (M + H))
[[
합성예Synthesis Example
68] 3-22의 합성 68] Synthesis of 3-22
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4-(dibenzo[b,d]furan-2-yl)-6-phenyl-1,3,5-triazine (17.6 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 47과 동일한 과정을 수행하여 목적 화합물인 3-22 (13.2 g, 수율 53%)를 얻었다.2- (3'-chloro- [1,1'-biphenyl] -3-yl) -4- (dibenzo [b, d] furan instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 2-yl) -6-phenyl-1,3,5-triazine (17.6 g, 34.4 mmol), the same procedure as in Synthesis Example 47 was carried out to provide 3-22 (13.2) as a target compound. g, yield 53%).
Mass (이론치: 792.94, 측정치: 793(M+H))Mass (Theoretical value: 792.94, Measured value: 793 (M + H))
[[
합성예Synthesis Example
69] 3-23의 합성 69] Synthesis of 3-23
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine (17.6 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 47과 동일한 과정을 수행하여 목적 화합물인 3-23 (13.2 g, 수율 53%)을 얻었다.2- (3'-chloro- [1,1'-biphenyl] -3-yl) -4- (dibenzo [b, d] furan instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using -1-yl) -6-phenyl-1,3,5-triazine (17.6 g, 34.4 mmol), the same procedure as in Synthesis Example 47 was carried out to provide 3-23 (13.2) as a target compound. g, yield 53%).
Mass (이론치: 792.94, 측정치: 793(M+H))Mass (Theoretical value: 792.94, Measured value: 793 (M + H))
[[
합성예Synthesis Example
70] 4-1의 합성 70] Synthesis of 4-1
질소 기류 하에서 Core-4 (10 g, 31.3 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (9.22 g, 34.4 mmol), CuI (0.596 g, 3.13 mmol), 1,10-phenanthroline (1.13 g, 6.26 mmol), Cs2CO3 (20.4 g, 62.6 mmol) 및 nitrobenzene (100 ml)를 혼합하고 210℃ 에서 3시간 동안 교반하였다. 반응이 종결된 후 고체염을 필터링한 후, 컬럼 크로마토그래피로 정제하여 목적 화합물인 4-1 (10.7 g, 수율 62%)을 얻었다.Core-4 (10 g, 31.3 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (9.22 g, 34.4 mmol), CuI (0.596 g, 3.13 mmol), 1, under a nitrogen stream. 10-phenanthroline (1.13 g, 6.26 mmol), Cs 2 CO 3 (20.4 g, 62.6 mmol) and nitrobenzene (100 ml) were mixed and stirred at 210 ° C. for 3 hours. After the reaction was terminated, the solid salt was filtered and purified by column chromatography to obtain the title compound 4-1 (10.7 g, yield 62%).
Mass (이론치: 550.67, 측정치: 551(M+H)) Mass (Theoretical value: 550.67, Measured value: 551 (M + H))
[[
합성예Synthesis Example
71] 4-2의 합성 71] Synthesis of 4-2
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (11.3 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 70과 동일한 과정을 수행하여 목적 화합물인 4-2 (12.6 g, 수율 64%)를 얻었다.2-([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3,5-triazine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using (11.3 g, 34.4 mmol), the same procedure as in Synthesis Example 70 was carried out to obtain 4-2 (12.6 g, yield 64%) of the title compound.
Mass (이론치: 626.76, 측정치: 627(M+H))Mass (Theoretical value: 626.76, Measured value: 627 (M + H))
[[
합성예Synthesis Example
72] 4-3의 합성 72] Synthesis of 4-3
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenylpyrimidine (11.3 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 70과 동일한 과정을 수행하여 목적 화합물인 4-3 (12.6 g, 수율 64%)을 얻었다.2-([1,1'-biphenyl] -4-yl) -4-chloro-6-phenylpyrimidine (11.3 g, 34.4 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using the same procedure as in Synthesis Example 70, the title compound 4-3 (12.6 g, yield 64%) was obtained.
Mass (이론치: 625.78, 측정치: 626(M+H))Mass (Theoretical value: 625.78, Measured value: 626 (M + H))
[[
합성예Synthesis Example
73] 4-4의 합성 73] Synthesis of 4-4
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (11.3 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 70과 동일한 과정을 수행하여 목적 화합물인 4-4 (12.6 g, 수율 64%)를 얻었다.Use of 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (11.3 g, 34.4 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except that in the same manner as in Synthesis Example 70 to give the title compound 4-4 (12.6 g, 64% yield).
Mass (이론치: 626.76, 측정치: 627(M+H))Mass (Theoretical value: 626.76, Measured value: 627 (M + H))
[[
합성예Synthesis Example
74] 4-5의 합성 74] Synthesis of 4-5
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 4-(3-chlorophenyl)-2,6-diphenylpyrimidine (11.3 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 70과 동일한 과정을 수행하여 목적 화합물인 4-5 (12.6 g, 수율 64%)를 얻었다.Synthesis Example 70 except that 4- (3-chlorophenyl) -2,6-diphenylpyrimidine (11.3 g, 34.4 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine. 4-5 (12.6 g, 64% yield) was obtained by the same procedure as the target compound.
Mass (이론치: 625.78, 측정치: 626(M+H))Mass (Theoretical value: 625.78, Measured value: 626 (M + H))
[[
합성예Synthesis Example
75] 4-6의 합성 75] Synthesis of 4-6
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine (14.5 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 70과 동일한 과정을 수행하여 목적 화합물인 4-6 (13.2 g, 수율 60%)을 얻었다.2-([1,1'-biphenyl] -4-yl) -4- (3-chlorophenyl) -6-phenyl-1,3 instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using, 5-triazine (14.5 g, 34.4 mmol), the same procedure as in Synthesis Example 70 was carried out to obtain 4-6 (13.2 g, yield 60%) as a target compound.
Mass (이론치: 702.86, 측정치: 703(M+H))Mass (Theoretical value: 702.86, Measured value: 703 (M + H))
[[
합성예Synthesis Example
76] 4-7의 합성 76] Synthesis of 4-7
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenylpyrimidine (14.5 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 70과 동일한 과정을 수행하여 목적 화합물인 4-7 (13.2 g, 수율 60%)을 얻었다.2-([1,1'-biphenyl] -4-yl) -4- (3-chlorophenyl) -6-phenylpyrimidine (14.5 g, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 34.4 mmol), the same procedure as in Synthesis Example 70 was carried out to obtain 4-7 (13.2 g, yield 60%) as a target compound.
Mass (이론치: 701.87, 측정치: 702(M+H))Mass (Theoretical value: 701.87, Measured value: 702 (M + H))
[[
합성예Synthesis Example
77] 4-8의 합성 77] Synthesis of 4-8
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine (14.5 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 70과 동일한 과정을 수행하여 목적 화합물인 4-8 (13.2 g, 수율 60%)을 얻었다.2- (3'-chloro- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 5-triazine (14.5 g, 34.4 mmol), the same procedure as in Synthesis Example 70 was carried out to obtain 4-8 (13.2 g, yield 60%) as a target compound.
Mass (이론치: 702.86, 측정치: 703(M+H))Mass (Theoretical value: 702.86, Measured value: 703 (M + H))
[[
합성예Synthesis Example
78] 4-9의 합성 78] Synthesis of 4-9
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine (14.5 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 70과 동일한 과정을 수행하여 목적 화합물인 4-9 (13.2 g, 수율 60%)를 얻었다.2- (3'-chloro- [1,1'-biphenyl] -4-yl) -4,6-diphenyl-1,3, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 5-triazine (14.5 g, 34.4 mmol), the same procedure as in Synthesis Example 70 was carried out to obtain 4-9 (13.2 g, yield 60%) as a target compound.
Mass (이론치: 702.86, 측정치: 703(M+H))Mass (Theoretical value: 702.86, Measured value: 703 (M + H))
[[
합성예Synthesis Example
79] 4-10의 합성 79] Synthesis of 4-10
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(4'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine (14.5 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 70과 동일한 과정을 수행하여 목적 화합물인 4-10 (13.2 g, 수율 60%)을 얻었다.2- (4'-chloro- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 5-triazine (14.5 g, 34.4 mmol), the same procedure as in Synthesis Example 70 was carried out to obtain 4-10 (13.2 g, yield 60%) as a target compound.
Mass (이론치: 702.86, 측정치: 703(M+H))Mass (Theoretical value: 702.86, Measured value: 703 (M + H))
[[
합성예Synthesis Example
80] 4-11의 합성 80] Synthesis of 4-11
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(4'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine (14.5 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 70과 동일한 과정을 수행하여 목적 화합물인 4-11 (13.2 g, 수율 60%)을 얻었다.2- (4'-chloro- [1,1'-biphenyl] -4-yl) -4,6-diphenyl-1,3, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 5-triazine (14.5 g, 34.4 mmol), the same procedure as in Synthesis Example 70 was carried out to obtain the title compound 4-11 (13.2 g, yield 60%).
Mass (이론치: 702.86, 측정치: 703(M+H))Mass (Theoretical value: 702.86, Measured value: 703 (M + H))
[[
합성예Synthesis Example
81] 4-12의 합성 81] Synthesis of 4-12
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-chloro-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine (12.3 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 70과 동일한 과정을 수행하여 목적 화합물인 4-12 (11.0 g, 수율 55%)를 얻었다.2-chloro-4- (dibenzo [b, d] furan-4-yl) -6-phenyl-1,3,5-triazine (instead of 2-chloro-4,6-diphenyl-1,3,5-triazine) 12.3 g, 34.4 mmol) was used and the same procedure as in Synthesis Example 70 was carried out to obtain 4-12 (11.0 g, 55% yield) of the title compound.
Mass (이론치: 640.75, 측정치: 641(M+H))Mass (Theoretical value: 640.75, Measured value: 641 (M + H))
[[
합성예Synthesis Example
82] 4-13의 합성 82] Synthesis of 4-13
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (12.3 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 70과 동일한 과정을 수행하여 목적 화합물인 4-13 (11.0 g, 수율 55%)을 얻었다.2-chloro-4- (dibenzo [b, d] furan-3-yl) -6-phenyl-1,3,5-triazine (instead of 2-chloro-4,6-diphenyl-1,3,5-triazine) 12.3 g, 34.4 mmol) was obtained, and the same procedure as in Synthesis Example 70 was performed, to obtain 4-13 (11.0 g, 55% yield) of the title compound.
Mass (이론치: 640.75, 측정치: 641(M+H))Mass (Theoretical value: 640.75, Measured value: 641 (M + H))
[[
합성예Synthesis Example
83] 4-14의 합성 83] Synthesis of 4-14
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-chloro-4-(dibenzo[b,d]furan-2-yl)-6-phenyl-1,3,5-triazine (12.3 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 70과 동일한 과정을 수행하여 목적 화합물인 4-14 (11.0 g, 수율 55%)를 얻었다.2-chloro-4- (dibenzo [b, d] furan-2-yl) -6-phenyl-1,3,5-triazine (instead of 2-chloro-4,6-diphenyl-1,3,5-triazine) Except for using 12.3 g, 34.4 mmol), the same procedure as in Synthesis Example 70 was carried out to obtain 4-14 (11.0 g, 55% yield) of the title compound.
Mass (이론치: 640.75, 측정치: 641(M+H))Mass (Theoretical value: 640.75, Measured value: 641 (M + H))
[[
합성예Synthesis Example
84] 4-15의 합성 84] Synthesis of 4-15
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-chloro-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine (12.3 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 70과 동일한 과정을 수행하여 목적 화합물인 4-15 (11.0 g, 수율 55%)를 얻었다.2-chloro-4- (dibenzo [b, d] furan-1-yl) -6-phenyl-1,3,5-triazine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine ( 12.3 g, 34.4 mmol) was obtained, and the same procedure as in Synthesis Example 70 was performed, to obtain 4-15 (11.0 g, 55% yield) of the title compound.
Mass (이론치: 640.75, 측정치: 641(M+H))Mass (Theoretical value: 640.75, Measured value: 641 (M + H))
[[
합성예Synthesis Example
85] 4-16의 합성 85] Synthesis Of 4-16
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3-chlorophenyl)-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine (14.9 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 70과 동일한 과정을 수행하여 목적 화합물인 4-16 (13.0 g, 수율 58%)을 얻었다.2- (3-chlorophenyl) -4- (dibenzo [b, d] furan-4-yl) -6-phenyl-1,3, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 5-triazine (14.9 g, 34.4 mmol), the same procedure as in Synthesis Example 70 was carried out to obtain the title compound 4-16 (13.0 g, yield 58%).
Mass (이론치: 716.84, 측정치: 717(M+H))Mass (Theoretical value: 716.84, Measured value: 717 (M + H))
[[
합성예Synthesis Example
86] 4-17의 합성 86] Synthesis of 4-17
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3-chlorophenyl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (14.9 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 70과 동일한 과정을 수행하여 목적 화합물인 4-17 (13.0 g, 수율 58%)을 얻었다.2- (3-chlorophenyl) -4- (dibenzo [b, d] furan-3-yl) -6-phenyl-1,3, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 5-triazine (14.9 g, 34.4 mmol), the same procedure as in Synthesis Example 70 was carried out to obtain 4-17 (13.0 g, yield 58%) as a target compound.
Mass (이론치: 716.84, 측정치: 717(M+H))Mass (Theoretical value: 716.84, Measured value: 717 (M + H))
[[
합성예Synthesis Example
87] 4-18의 합성 87] Synthesis of 4-18
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3-chlorophenyl)-4-(dibenzo[b,d]furan-2-yl)-6-phenyl-1,3,5-triazine (14.9 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 70과 동일한 과정을 수행하여 목적 화합물인 4-18 (13.0 g, 수율 58%)을 얻었다.2- (3-chlorophenyl) -4- (dibenzo [b, d] furan-2-yl) -6-phenyl-1,3, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 5-triazine (14.9 g, 34.4 mmol), the same procedure as in Synthesis Example 70 was carried out to obtain the title compound 4-18 (13.0 g, yield 58%).
Mass (이론치: 716.84, 측정치: 717(M+H))Mass (Theoretical value: 716.84, Measured value: 717 (M + H))
[[
합성예Synthesis Example
88] 4-19의 합성 88] Synthesis of 4-19
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3-chlorophenyl)-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine (14.9 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 70과 동일한 과정을 수행하여 목적 화합물인 4-19 (13.0 g, 수율 58%)를 얻었다.2- (3-chlorophenyl) -4- (dibenzo [b, d] furan-1-yl) -6-phenyl-1,3, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 5-triazine (14.9 g, 34.4 mmol), the same procedure as in Synthesis Example 70 was carried out to obtain 4-19 (13.0 g, yield 58%) as a target compound.
Mass (이론치: 716.84, 측정치: 717(M+H))Mass (Theoretical value: 716.84, Measured value: 717 (M + H))
[[
합성예Synthesis Example
89] 4-20의 합성 89] Synthesis of 4-20
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine (17.6 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 70과 동일한 과정을 수행하여 목적 화합물인 4-20 (13.2 g, 수율 53%)을 얻었다.2- (3'-chloro- [1,1'-biphenyl] -3-yl) -4- (dibenzo [b, d] furan instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 4-yl) -6-phenyl-1,3,5-triazine (17.6 g, 34.4 mmol), the same procedure as in Synthesis Example 70 was carried out to provide the title compound 4-20 (13.2 g, yield 53%).
Mass (이론치: 792.94, 측정치: 793(M+H))Mass (Theoretical value: 792.94, Measured value: 793 (M + H))
[[
합성예Synthesis Example
90] 4-21의 합성 90] Synthesis of 4-21
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (17.6 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 70과 동일한 과정을 수행하여 목적 화합물인 4-21 (13.2 g, 수율 53%)을 얻었다.2- (3'-chloro- [1,1'-biphenyl] -3-yl) -4- (dibenzo [b, d] furan instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using -3-yl) -6-phenyl-1,3,5-triazine (17.6 g, 34.4 mmol), the same procedure as in Synthesis Example 70 was carried out to provide the title compound 4-21 (13.2). g, yield 53%).
Mass (이론치: 792.94, 측정치: 793(M+H))Mass (Theoretical value: 792.94, Measured value: 793 (M + H))
[[
합성예Synthesis Example
91] 4-22의 합성 91] Synthesis of 4-22
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4-(dibenzo[b,d]furan-2-yl)-6-phenyl-1,3,5-triazine (17.6 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 70과 동일한 과정을 수행하여 목적 화합물인 4-22 (13.2 g, 수율 53%)를 얻었다.2- (3'-chloro- [1,1'-biphenyl] -3-yl) -4- (dibenzo [b, d] furan instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 2--2-yl) -6-phenyl-1,3,5-triazine (17.6 g, 34.4 mmol), the same procedure as in Synthesis Example 70 was carried out to provide 4-22 (13.2) as a target compound. g, yield 53%).
Mass (이론치: 792.94, 측정치: 793(M+H))Mass (Theoretical value: 792.94, Measured value: 793 (M + H))
[[
합성예Synthesis Example
92] 4-23의 합성 92] Synthesis of 4-23
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine (17.6 g, 34.4 mmol)을 사용하는 것을 제외하고는, 상기 합성예 70과 동일한 과정을 수행하여 목적 화합물인 4-23 (13.2 g, 수율 53%)을 얻었다.2- (3'-chloro- [1,1'-biphenyl] -3-yl) -4- (dibenzo [b, d] furan instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using -1-yl) -6-phenyl-1,3,5-triazine (17.6 g, 34.4 mmol), the same procedure as in Synthesis Example 70 was carried out to provide the title compound 4-23 (13.2). g, yield 53%).
Mass (이론치: 792.94, 측정치: 793(M+H))Mass (Theoretical value: 792.94, Measured value: 793 (M + H))
[[
합성예Synthesis Example
93] 5-1의 합성 93] Synthesis of 5-1
질소 기류 하에서 Core-5 (10 g, 25.2 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (7.45 g, 27.8 mmol), CuI (0.481 g, 2.52 mmol), 1,10-phenanthroline (0.911 g, 5.04 mmol), Cs2CO3 (16.5 g, 50.4 mmol) 및 nitrobenzene (100 ml)를 혼합하고 210℃ 에서 3시간 동안 교반하였다. 반응이 종결된 후 고체염을 필터링한 후, 컬럼 크로마토그래피로 정제하여 목적 화합물인 5-1 (10.8 g, 수율 68%)을 얻었다.Core-5 (10 g, 25.2 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (7.45 g, 27.8 mmol), CuI (0.481 g, 2.52 mmol), 1, under a nitrogen stream. 10-phenanthroline (0.911 g, 5.04 mmol), Cs 2 CO 3 (16.5 g, 50.4 mmol) and nitrobenzene (100 ml) were mixed and stirred at 210 ° C. for 3 hours. After completion of the reaction, the solid salt was filtered and purified by column chromatography to give the title compound 5-1 (10.8 g, yield 68%).
Mass (이론치: 626.76, 측정치: 627(M+H)) Mass (Theoretical value: 626.76, Measured value: 627 (M + H))
[[
합성예Synthesis Example
94] 5-2의 합성 94] Synthesis of 5-2
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (9.56 g, 27.8 mmol)을 사용하는 것을 제외하고는, 상기 합성예 93과 동일한 과정을 수행하여 목적 화합물인 5-2 (11.4 g, 수율 64%)를 얻었다.2-([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3,5-triazine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using (9.56 g, 27.8 mmol), the same procedure as in Synthesis Example 93 was carried out to obtain 5-2 (11.4 g, yield 64%) of the title compound.
Mass (이론치: 702.86, 측정치: 703(M+H))Mass (Theoretical value: 702.86, Measured value: 703 (M + H))
[[
합성예Synthesis Example
95] 5-3의 합성 95] Synthesis of 5-3
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenylpyrimidine (9.56 g, 27.8 mmol)을 사용하는 것을 제외하고는, 상기 합성예 93과 동일한 과정을 수행하여 목적 화합물인 5-3 (11.4 g, 수율 64%)을 얻었다.2-([1,1'-biphenyl] -4-yl) -4-chloro-6-phenylpyrimidine (9.56 g, 27.8 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using the same procedure as in Synthesis Example 93, the title compound was obtained 5-3 (11.4 g, 64% yield).
Mass (이론치: 701.87, 측정치: 702(M+H))Mass (Theoretical value: 701.87, Measured value: 702 (M + H))
[[
합성예Synthesis Example
96] 5-4의 합성 96] Synthesis of 5-4
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (9.56 g, 27.8 mmol)을 사용하는 것을 제외하고는, 상기 합성예 93과 동일한 과정을 수행하여 목적 화합물인 5-4 (11.4 g, 수율 64%)를 얻었다.Use of 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (9.56 g, 27.8 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except that, the same procedure as in Synthesis Example 93 was carried out to obtain 5-4 (11.4 g, yield 64%) of the target compound.
Mass (이론치: 702.86, 측정치: 703(M+H))Mass (Theoretical value: 702.86, Measured value: 703 (M + H))
[[
합성예Synthesis Example
97] 5-5의 합성 97] Synthesis of 5-5
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 4-(3-chlorophenyl)-2,6-diphenylpyrimidine (9.56 g, 27.8 mmol)을 사용하는 것을 제외하고는, 상기 합성예 93과 동일한 과정을 수행하여 목적 화합물인 5-5 (11.4 g, 수율 64%)를 얻었다.Synthesis Example 93 except that 4- (3-chlorophenyl) -2,6-diphenylpyrimidine (9.56 g, 27.8 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine. 5-5 (11.4 g, yield 64%) of the title compound was obtained.
Mass (이론치: 701.87, 측정치: 702(M+H))Mass (Theoretical value: 701.87, Measured value: 702 (M + H))
[[
합성예Synthesis Example
98] 5-6의 합성 98] Synthesis of 5-6
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine (11.7 g, 27.8 mmol)을 사용하는 것을 제외하고는, 상기 합성예 93과 동일한 과정을 수행하여 목적 화합물인 5-6 (11.8 g, 수율 60%)을 얻었다.2-([1,1'-biphenyl] -4-yl) -4- (3-chlorophenyl) -6-phenyl-1,3 instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 5-triazine (11.7 g, 27.8 mmol), the same procedure as in Synthesis Example 93 was carried out to obtain 5-6 (11.8 g, yield 60%) as a target compound.
Mass (이론치: 778.96, 측정치: 779(M+H))Mass (Theoretical value: 778.96, Measured value: 779 (M + H))
[[
합성예Synthesis Example
99] 5-7의 합성 99] Synthesis of 5-7
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenylpyrimidine (11.7 g, 27.8 mmol)을 사용하는 것을 제외하고는, 상기 합성예 93과 동일한 과정을 수행하여 목적 화합물인 5-7 (11.8 g, 수율 60%)을 얻었다.2-([1,1'-biphenyl] -4-yl) -4- (3-chlorophenyl) -6-phenylpyrimidine (11.7 g, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 27.8 mmol), the same procedure as in Synthesis Example 93 was carried out to obtain 5-7 (11.8 g, yield 60%) as a target compound.
Mass (이론치: 777.97, 측정치: 778(M+H))Mass (Theoretical value: 777.97, Measured value: 778 (M + H))
[[
합성예Synthesis Example
100] 5-8의 합성 100] Synthesis of 5-8
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine (11.7 g, 27.8 mmol)을 사용하는 것을 제외하고는, 상기 합성예 93과 동일한 과정을 수행하여 목적 화합물인 5-8 (11.8 g, 수율 60%)을 얻었다.2- (3'-chloro- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except that 5-triazine (11.7 g, 27.8 mmol) was used, the same procedure as in Synthesis Example 93 was carried out to obtain 5-8 (11.8 g, yield 60%) as a target compound.
Mass (이론치: 778.96, 측정치: 779(M+H))Mass (Theoretical value: 778.96, Measured value: 779 (M + H))
[[
합성예Synthesis Example
101] 5-9의 합성 101] Synthesis of 5-9
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine (11.7 g, 27.8 mmol)을 사용하는 것을 제외하고는, 상기 합성예 93과 동일한 과정을 수행하여 목적 화합물인 5-9 (11.8 g, 수율 60%)를 얻었다.2- (3'-chloro- [1,1'-biphenyl] -4-yl) -4,6-diphenyl-1,3, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except that 5-triazine (11.7 g, 27.8 mmol) was used, the same procedure as in Synthesis Example 93 was carried out to obtain 5-9 (11.8 g, yield 60%) as a target compound.
Mass (이론치: 778.96, 측정치: 779(M+H))Mass (Theoretical value: 778.96, Measured value: 779 (M + H))
[[
합성예Synthesis Example
102] 5-10의 합성 102] Synthesis of 5-10
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(4'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine (11.7 g, 27.8 mmol)을 사용하는 것을 제외하고는, 상기 합성예 93과 동일한 과정을 수행하여 목적 화합물인 5-10 (11.8 g, 수율 60%)을 얻었다.2- (4'-chloro- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 5-triazine (11.7 g, 27.8 mmol), the same procedure as in Synthesis Example 93 was carried out to obtain 5-10 (11.8 g, yield 60%) as a target compound.
Mass (이론치: 778.96, 측정치: 779(M+H))Mass (Theoretical value: 778.96, Measured value: 779 (M + H))
[[
합성예Synthesis Example
103] 5-11의 합성 103] Synthesis of 5-11
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(4'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine (11.7 g, 27.8 mmol)을 사용하는 것을 제외하고는, 상기 합성예 93과 동일한 과정을 수행하여 목적 화합물인 5-11 (11.8 g, 수율 60%)을 얻었다.2- (4'-chloro- [1,1'-biphenyl] -4-yl) -4,6-diphenyl-1,3, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 5-triazine (11.7 g, 27.8 mmol), the same procedure as in Synthesis Example 93 was carried out to obtain the title compound 5-11 (11.8 g, yield 60%).
Mass (이론치: 778.96, 측정치: 779(M+H))Mass (Theoretical value: 778.96, Measured value: 779 (M + H))
[[
합성예Synthesis Example
104] 5-12의 합성 104] Synthesis of 5-12
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-chloro-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine (9.95 g, 27.8 mmol)을 사용하는 것을 제외하고는, 상기 합성예 93과 동일한 과정을 수행하여 목적 화합물인 5-12 (9.97 g, 수율 55%)를 얻었다.2-chloro-4- (dibenzo [b, d] furan-4-yl) -6-phenyl-1,3,5-triazine (instead of 2-chloro-4,6-diphenyl-1,3,5-triazine) Except for using 9.95 g, 27.8 mmol), the same procedure as in Synthesis Example 93 was performed, to obtain 5-12 (9.97 g, yield 55%) of the title compound.
Mass (이론치: 716.84, 측정치: 717(M+H))Mass (Theoretical value: 716.84, Measured value: 717 (M + H))
[[
합성예Synthesis Example
105] 5-13의 합성 105] Synthesis of 5-13
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (9.95 g, 27.8 mmol)을 사용하는 것을 제외하고는, 상기 합성예 93과 동일한 과정을 수행하여 목적 화합물인 5-13 (9.97 g, 수율 55%)을 얻었다.2-chloro-4- (dibenzo [b, d] furan-3-yl) -6-phenyl-1,3,5-triazine (instead of 2-chloro-4,6-diphenyl-1,3,5-triazine) Except for using 9.95 g, 27.8 mmol), the same procedure as in Synthesis Example 93 was carried out to obtain 5-13 (9.97 g, 55% yield) of the title compound.
Mass (이론치: 716.84, 측정치: 717(M+H))Mass (Theoretical value: 716.84, Measured value: 717 (M + H))
[[
합성예Synthesis Example
106] 5-14의 합성 106] Synthesis of 5-14
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-chloro-4-(dibenzo[b,d]furan-2-yl)-6-phenyl-1,3,5-triazine (9.95 g, 27.8 mmol)을 사용하는 것을 제외하고는, 상기 합성예 93과 동일한 과정을 수행하여 목적 화합물인 5-14 (9.97 g, 수율 55%)를 얻었다.2-chloro-4- (dibenzo [b, d] furan-2-yl) -6-phenyl-1,3,5-triazine (instead of 2-chloro-4,6-diphenyl-1,3,5-triazine) Except for using 9.95 g, 27.8 mmol), to obtain the target compound 5-14 (9.97 g, 55% yield) by the same process as in Synthesis Example 93.
Mass (이론치: 716.84, 측정치: 717(M+H))Mass (Theoretical value: 716.84, Measured value: 717 (M + H))
[[
합성예Synthesis Example
107] 5-15의 합성 107] Synthesis of 5-15
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-chloro-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine (9.95 g, 27.8 mmol)을 사용하는 것을 제외하고는, 상기 합성예 93과 동일한 과정을 수행하여 목적 화합물인 5-15 (9.97 g, 수율 55%)를 얻었다.2-chloro-4- (dibenzo [b, d] furan-1-yl) -6-phenyl-1,3,5-triazine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine ( Except for using 9.95 g, 27.8 mmol), the same procedure as in Synthesis Example 93 was carried out to obtain 5-15 (9.97 g, 55% yield) of the title compound.
Mass (이론치: 716.84, 측정치: 717(M+H))Mass (Theoretical value: 716.84, Measured value: 717 (M + H))
[[
합성예Synthesis Example
108] 5-16의 합성 108] Synthesis of 5-16
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3-chlorophenyl)-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine (12.1 g, 27.8 mmol)을 사용하는 것을 제외하고는, 상기 합성예 93과 동일한 과정을 수행하여 목적 화합물인 5-16 (11.6 g, 수율 58%)을 얻었다.2- (3-chlorophenyl) -4- (dibenzo [b, d] furan-4-yl) -6-phenyl-1,3, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 5-triazine (12.1 g, 27.8 mmol), the same procedure as in Synthesis Example 93 was carried out to obtain 5-16 (11.6 g, yield 58%) of the target compound.
Mass (이론치: 792.94, 측정치: 793(M+H))Mass (Theoretical value: 792.94, Measured value: 793 (M + H))
[[
합성예Synthesis Example
109] 5-17의 합성 109] Synthesis of 5-17
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3-chlorophenyl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (12.1 g, 27.8 mmol)을 사용하는 것을 제외하고는, 상기 합성예 93과 동일한 과정을 수행하여 목적 화합물인 5-17 (11.6 g, 수율 58%)을 얻었다.2- (3-chlorophenyl) -4- (dibenzo [b, d] furan-3-yl) -6-phenyl-1,3, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 5-triazine (12.1 g, 27.8 mmol), the same procedure as in Synthesis Example 93 was carried out to obtain 5-17 (11.6 g, yield 58%) of the title compound.
Mass (이론치: 792.94, 측정치: 793(M+H))Mass (Theoretical value: 792.94, Measured value: 793 (M + H))
[[
합성예Synthesis Example
110] 5-18의 합성 110] Synthesis of 5-18
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3-chlorophenyl)-4-(dibenzo[b,d]furan-2-yl)-6-phenyl-1,3,5-triazine (12.1 g, 27.8 mmol)을 사용하는 것을 제외하고는, 상기 합성예 93과 동일한 과정을 수행하여 목적 화합물인 5-18 (11.6 g, 수율 58%)을 얻었다.2- (3-chlorophenyl) -4- (dibenzo [b, d] furan-2-yl) -6-phenyl-1,3, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 5-triazine (12.1 g, 27.8 mmol), the same procedure as in Synthesis Example 93 was carried out to obtain 5-18 (11.6 g, yield 58%) of the target compound.
Mass (이론치: 792.94, 측정치: 793(M+H))Mass (Theoretical value: 792.94, Measured value: 793 (M + H))
[[
합성예Synthesis Example
111] 5-19의 합성 111] Synthesis of 5-19
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3-chlorophenyl)-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine (12.1 g, 27.8 mmol)을 사용하는 것을 제외하고는, 상기 합성예 93과 동일한 과정을 수행하여 목적 화합물인 5-19 (11.6 g, 수율 58%)를 얻었다.2- (3-chlorophenyl) -4- (dibenzo [b, d] furan-1-yl) -6-phenyl-1,3, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 5-triazine (12.1 g, 27.8 mmol), the same procedure as in Synthesis Example 93 was performed to obtain 5-19 (11.6 g, yield 58%) as a target compound.
Mass (이론치: 792.94, 측정치: 793(M+H))Mass (Theoretical value: 792.94, Measured value: 793 (M + H))
[[
합성예Synthesis Example
112] 5-20의 합성 112] Synthesis of 5-20
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine (14.2 g, 27.8 mmol)을 사용하는 것을 제외하고는, 상기 합성예 93과 동일한 과정을 수행하여 목적 화합물인 5-20 (11.6 g, 수율 53%)을 얻었다.2- (3'-chloro- [1,1'-biphenyl] -3-yl) -4- (dibenzo [b, d] furan instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 4-yl) -6-phenyl-1,3,5-triazine (14.2 g, 27.8 mmol), the same procedure as in Synthesis Example 93 was carried out to obtain the title compound 5-20 (11.6). g, yield 53%).
Mass (이론치: 869.04, 측정치: 870(M+H))Mass (Theoretical value: 869.04, Measured value: 870 (M + H))
[[
합성예Synthesis Example
113] 5-21의 합성 113] Synthesis of 5-21
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (14.2 g, 27.8 mmol)을 사용하는 것을 제외하고는, 상기 합성예 93과 동일한 과정을 수행하여 목적 화합물인 5-21 (11.6 g, 수율 53%)을 얻었다.2- (3'-chloro- [1,1'-biphenyl] -3-yl) -4- (dibenzo [b, d] furan instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using -3-yl) -6-phenyl-1,3,5-triazine (14.2 g, 27.8 mmol), the same procedure as in Synthesis Example 93 was carried out to provide the title compound 5-21 (11.6). g, yield 53%).
Mass (이론치: 869.04, 측정치: 870(M+H))Mass (Theoretical value: 869.04, Measured value: 870 (M + H))
[[
합성예Synthesis Example
114] 5-22의 합성 114] Synthesis of 5-22
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4-(dibenzo[b,d]furan-2-yl)-6-phenyl-1,3,5-triazine (14.2 g, 27.8 mmol)을 사용하는 것을 제외하고는, 상기 합성예 93과 동일한 과정을 수행하여 목적 화합물인 5-22 (11.6 g, 수율 53%)를 얻었다.2- (3'-chloro- [1,1'-biphenyl] -3-yl) -4- (dibenzo [b, d] furan instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using -2-yl) -6-phenyl-1,3,5-triazine (14.2 g, 27.8 mmol), the same procedure as in Synthesis Example 93 was carried out to provide the title compound 5-22 (11.6). g, yield 53%).
Mass (이론치: 869.04, 측정치: 870(M+H))Mass (Theoretical value: 869.04, Measured value: 870 (M + H))
[[
합성예Synthesis Example
115] 5-23의 합성 115] Synthesis of 5-23
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine (14.2 g, 27.8 mmol)을 사용하는 것을 제외하고는, 상기 합성예 93과 동일한 과정을 수행하여 목적 화합물인 5-23 (11.6 g, 수율 53%)을 얻었다.2- (3'-chloro- [1,1'-biphenyl] -3-yl) -4- (dibenzo [b, d] furan instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using -1-yl) -6-phenyl-1,3,5-triazine (14.2 g, 27.8 mmol), the same procedure as in Synthesis Example 93 was carried out to provide the title compound 5-23 (11.6). g, yield 53%).
Mass (이론치: 869.04, 측정치: 870(M+H))Mass (Theoretical value: 869.04, Measured value: 870 (M + H))
[[
합성예Synthesis Example
116] 6-1의 합성 116] Synthesis of 6-1
질소 기류 하에서 Core-6 (10 g, 34.1 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (10.0 g, 37.5 mmol), CuI (0.649 g, 3.411 mmol), 1,10-phenanthroline (1.23 g, 6.82 mmol), Cs2CO3 (22.2 g, 68.2 mmol) 및 nitrobenzene (100 ml)를 혼합하고 210℃ 에서 3시간 동안 교반하였다. 반응이 종결된 후 고체염을 필터링한 후, 컬럼 크로마토그래피로 정제하여 목적 화합물인 6-1 (11.1 g, 수율 62%)을 얻었다.Core-6 (10 g, 34.1 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (10.0 g, 37.5 mmol), CuI (0.649 g, 3.411 mmol), 1, under a nitrogen stream. 10-phenanthroline (1.23 g, 6.82 mmol), Cs 2 CO 3 (22.2 g, 68.2 mmol) and nitrobenzene (100 ml) were mixed and stirred at 210 ° C. for 3 hours. After the reaction was terminated, the solid salt was filtered and purified by column chromatography to obtain the title compound 6-1 (11.1 g, yield 62%).
Mass (이론치: 524.63, 측정치: 525(M+H))Mass (Theoretical value: 524.63, Measured value: 525 (M + H))
[[
합성예Synthesis Example
117] 6-2의 합성 117] Synthesis of 6-2
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (12.9 g, 37.5 mmol)을 사용하는 것을 제외하고는, 상기 합성예 116과 동일한 과정을 수행하여 목적 화합물인 6-2 (12.3 g, 수율 60%)를 얻었다.2-([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3,5-triazine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using (12.9 g, 37.5 mmol), the same procedure as in Synthesis Example 116 was carried out to obtain 6-2 (12.3 g, yield 60%) as a target compound.
Mass (이론치: 600.73, 측정치: 601(M+H))Mass (Theoretical value: 600.73, Measured value: 601 (M + H))
[[
합성예Synthesis Example
118] 6-3의 합성 118] Synthesis of 6-3
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenylpyrimidine (12.9 g, 37.5 mmol)을 사용하는 것을 제외하고는, 상기 합성예 116과 동일한 과정을 수행하여 목적 화합물인 6-3 (12.3 g, 수율 60%)을 얻었다.2-([1,1'-biphenyl] -4-yl) -4-chloro-6-phenylpyrimidine (12.9 g, 37.5 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using, the same procedure as in Synthesis Example 116 was performed to obtain 6-3 (12.3 g, yield 60%) as a target compound.
Mass (이론치: 599.74, 측정치: 600(M+H))Mass (Theoretical value: 599.74, Measured value: 600 (M + H))
[[
합성예Synthesis Example
119] 6-4의 합성 119] Synthesis of 6-4
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (12.9 g, 37.5 mmol)을 사용하는 것을 제외하고는, 상기 합성예 116과 동일한 과정을 수행하여 목적 화합물인 6-4 (12.3 g, 수율 60%)를 얻었다.The use of 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (12.9 g, 37.5 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except that in the same manner as in Synthesis Example 116 to give the title compound 6-4 (12.3 g, yield 60%).
Mass (이론치: 600.73, 측정치: 601(M+H))Mass (Theoretical value: 600.73, Measured value: 601 (M + H))
[[
합성예Synthesis Example
120] 6-5의 합성 120] Synthesis of 6-5
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 4-(3-chlorophenyl)-2,6-diphenylpyrimidine (12.9 g, 37.5 mmol)을 사용하는 것을 제외하고는, 상기 합성예 116과 동일한 과정을 수행하여 목적 화합물인 6-5 (12.3 g, 수율 60%)를 얻었다.Synthesis Example 116 except that 4- (3-chlorophenyl) -2,6-diphenylpyrimidine (12.9 g, 37.5 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine. 6-5 (12.3 g, yield 60%) as a target compound was obtained.
Mass (이론치: 599.74, 측정치: 600(M+H))Mass (Theoretical value: 599.74, Measured value: 600 (M + H))
[[
합성예Synthesis Example
121] 6-6의 합성 121] Synthesis of 6-6
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine (15.7 g, 37.5 mmol)을 사용하는 것을 제외하고는, 상기 합성예 116과 동일한 과정을 수행하여 목적 화합물인 6-6 (14.3 g, 수율 62%)을 얻었다.2-([1,1'-biphenyl] -4-yl) -4- (3-chlorophenyl) -6-phenyl-1,3 instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using, 5-triazine (15.7 g, 37.5 mmol), the same procedure as in Synthesis Example 116 was carried out to obtain 6-6 (14.3 g, yield 62%) as a target compound.
Mass (이론치: 676.82, 측정치: 677(M+H))Mass (Theoretical value: 676.82, Measured value: 677 (M + H))
[[
합성예Synthesis Example
122] 6-7의 합성 122] Synthesis of 6-7
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenylpyrimidine (15.7 g, 37.5 mmol)을 사용하는 것을 제외하고는, 상기 합성예 116과 동일한 과정을 수행하여 목적 화합물인 6-7 (14.3 g, 수율 62%)을 얻었다.2-([1,1'-biphenyl] -4-yl) -4- (3-chlorophenyl) -6-phenylpyrimidine (15.7 g, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 37.5 mmol), the same procedure as in Synthesis Example 116 was performed, to obtain 6-7 (14.3 g, yield 62%) of the title compound.
Mass (이론치: 675.84, 측정치: 676(M+H))Mass (Theoretical value: 675.84, Measured value: 676 (M + H))
[[
합성예Synthesis Example
123] 6-8의 합성 123] Synthesis of 6-8
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine (15.7 g, 37.5 mmol)을 사용하는 것을 제외하고는, 상기 합성예 116과 동일한 과정을 수행하여 목적 화합물인 6-8 (14.3 g, 수율 62%)을 얻었다.2- (3'-chloro- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except that 5-triazine (15.7 g, 37.5 mmol) was used, the same procedure as in Synthesis Example 116 was carried out to obtain 6-8 (14.3 g, yield 62%) as a target compound.
Mass (이론치: 676.82, 측정치: 677(M+H))Mass (Theoretical value: 676.82, Measured value: 677 (M + H))
[[
합성예Synthesis Example
124] 6-9의 합성 124] Synthesis of 6-9
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine (15.7 g, 37.5 mmol)을 사용하는 것을 제외하고는, 상기 합성예 116과 동일한 과정을 수행하여 목적 화합물인 6-9 (14.3 g, 수율 62%)를 얻었다.2- (3'-chloro- [1,1'-biphenyl] -4-yl) -4,6-diphenyl-1,3, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 5-triazine (15.7 g, 37.5 mmol), the same procedure as in Synthesis Example 116 was carried out to obtain the title compound 6-9 (14.3 g, yield 62%).
Mass (이론치: 676.82, 측정치: 677(M+H))Mass (Theoretical value: 676.82, Measured value: 677 (M + H))
[[
합성예Synthesis Example
125] 6-10의 합성 125] Synthesis of 6-10
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(4'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine (15.7 g, 37.5 mmol)을 사용하는 것을 제외하고는, 상기 합성예 116과 동일한 과정을 수행하여 목적 화합물인 6-10 (14.3 g, 수율 62%)을 얻었다.2- (4'-chloro- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 5-triazine (15.7 g, 37.5 mmol), the same procedure as in Synthesis Example 116 was carried out to obtain the title compound 6-10 (14.3 g, yield 62%).
Mass (이론치: 676.82, 측정치: 677(M+H))Mass (Theoretical value: 676.82, Measured value: 677 (M + H))
[[
합성예Synthesis Example
126] 6-11의 합성 126] Synthesis of 6-11
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(4'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine (15.7 g, 37.5 mmol)을 사용하는 것을 제외하고는, 상기 합성예 116과 동일한 과정을 수행하여 목적 화합물인 6-11 (14.3 g, 수율 62%)을 얻었다.2- (4'-chloro- [1,1'-biphenyl] -4-yl) -4,6-diphenyl-1,3, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 5-triazine (15.7 g, 37.5 mmol), the same procedure as in Synthesis Example 116 was carried out to obtain the title compound 6-11 (14.3 g, yield 62%).
Mass (이론치: 676.82, 측정치: 677(M+H))Mass (Theoretical value: 676.82, Measured value: 677 (M + H))
[[
합성예Synthesis Example
127] 6-12의 합성 127] Synthesis of 6-12
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-chloro-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine (13.4 g, 37.5 mmol)을 사용하는 것을 제외하고는, 상기 합성예 116과 동일한 과정을 수행하여 목적 화합물인 6-12 (12.8 g, 수율 61%)를 얻었다.2-chloro-4- (dibenzo [b, d] furan-4-yl) -6-phenyl-1,3,5-triazine (instead of 2-chloro-4,6-diphenyl-1,3,5-triazine) Except for using 13.4 g, 37.5 mmol), the same procedure as in Synthesis Example 116 was performed, to obtain 6-12 (12.8 g, 61%) of the title compound.
Mass (이론치: 614.71, 측정치: 615(M+H))Mass (Theoretical value: 614.71, Measured value: 615 (M + H))
[[
합성예Synthesis Example
128] 6-13의 합성 128] Synthesis of 6-13
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (13.4 g, 37.5 mmol)을 사용하는 것을 제외하고는, 상기 합성예 116과 동일한 과정을 수행하여 목적 화합물인 6-13 (12.8 g, 수율 61%)을 얻었다.2-chloro-4- (dibenzo [b, d] furan-3-yl) -6-phenyl-1,3,5-triazine (instead of 2-chloro-4,6-diphenyl-1,3,5-triazine) 13.4 g, 37.5 mmol) was obtained in the same manner as in Synthesis Example 116 to obtain 6-13 (12.8 g, 61% yield) of the title compound.
Mass (이론치: 614.71, 측정치: 615(M+H))Mass (Theoretical value: 614.71, Measured value: 615 (M + H))
[[
합성예Synthesis Example
129] 6-14의 합성 129] Synthesis of 6-14
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-chloro-4-(dibenzo[b,d]furan-2-yl)-6-phenyl-1,3,5-triazine (13.4 g, 37.5 mmol)을 사용하는 것을 제외하고는, 상기 합성예 116과 동일한 과정을 수행하여 목적 화합물인 6-14 (12.8 g, 수율 61%)를 얻었다.2-chloro-4- (dibenzo [b, d] furan-2-yl) -6-phenyl-1,3,5-triazine (instead of 2-chloro-4,6-diphenyl-1,3,5-triazine) 13.4 g, 37.5 mmol) was obtained in the same manner as in Synthesis Example 116, to obtain 6-14 (12.8 g, 61% yield) of the title compound.
Mass (이론치: 614.71, 측정치: 615(M+H))Mass (Theoretical value: 614.71, Measured value: 615 (M + H))
[[
합성예Synthesis Example
130] 6-15의 합성 130] Synthesis of 6-15
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-chloro-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine (13.4 g, 37.5 mmol)을 사용하는 것을 제외하고는, 상기 합성예 116과 동일한 과정을 수행하여 목적 화합물인 6-15 (12.8 g, 수율 61%)를 얻었다.2-chloro-4- (dibenzo [b, d] furan-1-yl) -6-phenyl-1,3,5-triazine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine ( Except for using 13.4 g, 37.5 mmol), the same procedure as in Synthesis Example 116 was performed, to obtain 6-15 (12.8 g, 61%) of the title compound.
Mass (이론치: 614.71, 측정치: 615(M+H))Mass (Theoretical value: 614.71, Measured value: 615 (M + H))
[[
합성예Synthesis Example
131] 6-16의 합성 131] Synthesis of 6-16
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3-chlorophenyl)-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine (16.3 g, 37.5 mmol)을 사용하는 것을 제외하고는, 상기 합성예 116과 동일한 과정을 수행하여 목적 화합물인 6-16 (13.7 g, 수율 58%)을 얻었다.2- (3-chlorophenyl) -4- (dibenzo [b, d] furan-4-yl) -6-phenyl-1,3, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 5-triazine (16.3 g, 37.5 mmol), the same procedure as in Synthesis Example 116 was carried out to obtain the title compound 6-16 (13.7 g, yield 58%).
Mass (이론치: 690.81, 측정치: 691(M+H))Mass (Theoretical value: 690.81, Measured value: 691 (M + H))
[[
합성예Synthesis Example
132] 6-17의 합성 132] Synthesis of 6-17
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3-chlorophenyl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (16.3 g, 37.5 mmol)을 사용하는 것을 제외하고는, 상기 합성예 116과 동일한 과정을 수행하여 목적 화합물인 6-17 (13.7 g, 수율 58%)을 얻었다.2- (3-chlorophenyl) -4- (dibenzo [b, d] furan-3-yl) -6-phenyl-1,3, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except that 5-triazine (16.3 g, 37.5 mmol) was used, the same procedure as in Synthesis Example 116 was carried out to obtain 6-17 (13.7 g, yield 58%) of the title compound.
Mass (이론치: 690.81, 측정치: 691(M+H))Mass (Theoretical value: 690.81, Measured value: 691 (M + H))
[[
합성예Synthesis Example
133] 6-18의 합성 133] Synthesis of 6-18
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3-chlorophenyl)-4-(dibenzo[b,d]furan-2-yl)-6-phenyl-1,3,5-triazine (16.3 g, 37.5 mmol)을 사용하는 것을 제외하고는, 상기 합성예 116과 동일한 과정을 수행하여 목적 화합물인 6-18 (13.7 g, 수율 58%)을 얻었다.2- (3-chlorophenyl) -4- (dibenzo [b, d] furan-2-yl) -6-phenyl-1,3, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 5-triazine (16.3 g, 37.5 mmol), the same procedure as in Synthesis Example 116 was carried out to obtain the title compound 6-18 (13.7 g, yield 58%).
Mass (이론치: 690.81, 측정치: 691(M+H))Mass (Theoretical value: 690.81, Measured value: 691 (M + H))
[[
합성예Synthesis Example
134] 6-19의 합성 134] Synthesis of 6-19
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3-chlorophenyl)-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine (16.3 g, 37.5 mmol)을 사용하는 것을 제외하고는, 상기 합성예 116과 동일한 과정을 수행하여 목적 화합물인 6-19 (13.7 g, 수율 58%)를 얻었다.2- (3-chlorophenyl) -4- (dibenzo [b, d] furan-1-yl) -6-phenyl-1,3, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 5-triazine (16.3 g, 37.5 mmol), the same procedure as in Synthesis Example 116 was carried out to obtain the title compound 6-19 (13.7 g, yield 58%).
Mass (이론치: 690.81, 측정치: 691(M+H))Mass (Theoretical value: 690.81, Measured value: 691 (M + H))
[[
합성예Synthesis Example
135] 6-20의 합성 135] Synthesis of 6-20
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine (19.1 g, 37.5 mmol)을 사용하는 것을 제외하고는, 상기 합성예 116과 동일한 과정을 수행하여 목적 화합물인 6-20 (15.8 g, 수율 55%)을 얻었다.2- (3'-chloro- [1,1'-biphenyl] -3-yl) -4- (dibenzo [b, d] furan instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 4-yl) -6-phenyl-1,3,5-triazine (19.1 g, 37.5 mmol), the same procedure as in Synthesis Example 116 was carried out to obtain 6-20 (15.8) as a target compound. g, yield 55%) was obtained.
Mass (이론치: 766.90, 측정치: 767(M+H))Mass (Theoretical value: 766.90, Measured value: 767 (M + H))
[[
합성예Synthesis Example
136] 6-21의 합성 136] Synthesis of 6-21
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (19.1 g, 37.5 mmol)을 사용하는 것을 제외하고는, 상기 합성예 116과 동일한 과정을 수행하여 목적 화합물인 6-21 (15.8 g, 수율 55%)을 얻었다.2- (3'-chloro- [1,1'-biphenyl] -3-yl) -4- (dibenzo [b, d] furan instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using -3-yl) -6-phenyl-1,3,5-triazine (19.1 g, 37.5 mmol), the same procedure as in Synthesis Example 116 was carried out to obtain 6-21 (15.8) as a target compound. g, yield 55%) was obtained.
Mass (이론치: 766.90, 측정치: 767(M+H))Mass (Theoretical value: 766.90, Measured value: 767 (M + H))
[[
합성예Synthesis Example
137] 6-22의 합성 137] Synthesis of 6-22
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4-(dibenzo[b,d]furan-2-yl)-6-phenyl-1,3,5-triazine (19.1 g, 37.5 mmol)을 사용하는 것을 제외하고는, 상기 합성예 116과 동일한 과정을 수행하여 목적 화합물인 6-22 (15.8 g, 수율 55%)를 얻었다.2- (3'-chloro- [1,1'-biphenyl] -3-yl) -4- (dibenzo [b, d] furan instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using -2-yl) -6-phenyl-1,3,5-triazine (19.1 g, 37.5 mmol), the same procedure as in Synthesis Example 116 was carried out to give 6-22 (15.8) as a target compound. g, yield 55%) was obtained.
Mass (이론치: 766.90, 측정치: 767(M+H))Mass (Theoretical value: 766.90, Measured value: 767 (M + H))
[[
합성예Synthesis Example
138] 6-23의 합성 138] Synthesis of 6-23
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine (19.1 g, 37.5 mmol)을 사용하는 것을 제외하고는, 상기 합성예 116과 동일한 과정을 수행하여 목적 화합물인 6-23 (15.8 g, 수율 55%)을 얻었다.2- (3'-chloro- [1,1'-biphenyl] -3-yl) -4- (dibenzo [b, d] furan instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using -1-yl) -6-phenyl-1,3,5-triazine (19.1 g, 37.5 mmol), the same procedure as in Synthesis Example 116 was carried out to obtain 6-23 (15.8) as a target compound. g, yield 55%) was obtained.
Mass (이론치: 766.90, 측정치: 767(M+H))Mass (Theoretical value: 766.90, Measured value: 767 (M + H))
[[
합성예Synthesis Example
139] 7-1의 합성 139] Synthesis of 7-1
질소 기류 하에서 Core-7 (10 g, 34.1 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (10.0 g, 37.5 mmol), CuI (0.649 g, 3.411 mmol), 1,10-phenanthroline (1.23 g, 6.82 mmol), Cs2CO3 (22.2 g, 68.2 mmol) 및 nitrobenzene (100 ml)를 혼합하고 210℃ 에서 3시간 동안 교반하였다. 반응이 종결된 후 고체염을 필터링한 후, 컬럼 크로마토그래피로 정제하여 목적 화합물인 7-1 (11.1 g, 수율 62%)을 얻었다.Core-7 (10 g, 34.1 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (10.0 g, 37.5 mmol), CuI (0.649 g, 3.411 mmol), 1, under a nitrogen stream. 10-phenanthroline (1.23 g, 6.82 mmol), Cs 2 CO 3 (22.2 g, 68.2 mmol) and nitrobenzene (100 ml) were mixed and stirred at 210 ° C. for 3 hours. After completion of the reaction, the solid salt was filtered and purified by column chromatography to obtain the title compound 7-1 (11.1 g, yield 62%).
Mass (이론치: 524.63, 측정치: 525(M+H))Mass (Theoretical value: 524.63, Measured value: 525 (M + H))
[[
합성예Synthesis Example
140] 7-2의 합성 140] Synthesis of 7-2
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (12.9 g, 37.5 mmol)을 사용하는 것을 제외하고는, 상기 합성예 139와 동일한 과정을 수행하여 목적 화합물인 7-2 (12.3 g, 수율 60%)를 얻었다.2-([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3,5-triazine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using (12.9 g, 37.5 mmol), to obtain the target compound 7-2 (12.3 g, yield 60%) by the same procedure as in Synthesis Example 139.
Mass (이론치: 600.73, 측정치: 601(M+H))Mass (Theoretical value: 600.73, Measured value: 601 (M + H))
[[
합성예Synthesis Example
141] 7-3의 합성 141] Synthesis of 7-3
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenylpyrimidine (12.9 g, 37.5 mmol)을 사용하는 것을 제외하고는, 상기 합성예 139와 동일한 과정을 수행하여 목적 화합물인 7-3 (12.3 g, 수율 60%)을 얻었다.2-([1,1'-biphenyl] -4-yl) -4-chloro-6-phenylpyrimidine (12.9 g, 37.5 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using the same procedure as in Synthesis Example 139, the title compound was obtained 7-3 (12.3 g, yield 60%).
Mass (이론치: 599.74, 측정치: 600(M+H))Mass (Theoretical value: 599.74, Measured value: 600 (M + H))
[[
합성예Synthesis Example
142] 7-4의 합성 142] Synthesis of 7-4
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (12.9 g, 37.5 mmol)을 사용하는 것을 제외하고는, 상기 합성예 139와 동일한 과정을 수행하여 목적 화합물인 7-4 (12.3 g, 수율 60%)를 얻었다.The use of 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (12.9 g, 37.5 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except that in the same manner as in Synthesis Example 139 to obtain the title compound 7-4 (12.3 g, yield 60%).
Mass (이론치: 600.73, 측정치: 601(M+H))Mass (Theoretical value: 600.73, Measured value: 601 (M + H))
[[
합성예Synthesis Example
143] 7-5의 합성 143] Synthesis of 7-5
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 4-(3-chlorophenyl)-2,6-diphenylpyrimidine (12.9 g, 37.5 mmol)을 사용하는 것을 제외하고는, 상기 합성예 139와 동일한 과정을 수행하여 목적 화합물인 7-5 (12.3 g, 수율 60%)를 얻었다.Synthesis Example 139, except that 4- (3-chlorophenyl) -2,6-diphenylpyrimidine (12.9 g, 37.5 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine 7-5 (12.3 g, yield 60%) was obtained by the same procedure as the target compound.
Mass (이론치: 599.74, 측정치: 600(M+H))Mass (Theoretical value: 599.74, Measured value: 600 (M + H))
[[
합성예Synthesis Example
144] 7-6의 합성 144] Synthesis of 7-6
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine (15.7 g, 37.5 mmol)을 사용하는 것을 제외하고는, 상기 합성예 139와 동일한 과정을 수행하여 목적 화합물인 7-6 (14.3 g, 수율 62%)을 얻었다.2-([1,1'-biphenyl] -4-yl) -4- (3-chlorophenyl) -6-phenyl-1,3 instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using, 5-triazine (15.7 g, 37.5 mmol), to obtain the target compound 7-6 (14.3 g, yield 62%) was carried out in the same manner as in Synthesis Example 139.
Mass (이론치: 676.82, 측정치: 677(M+H))Mass (Theoretical value: 676.82, Measured value: 677 (M + H))
[[
합성예Synthesis Example
145] 7-7의 합성 145] Synthesis of 7-7
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenylpyrimidine (15.7 g, 37.5 mmol)을 사용하는 것을 제외하고는, 상기 합성예 139와 동일한 과정을 수행하여 목적 화합물인 7-7 (14.3 g, 수율 62%)을 얻었다.2-([1,1'-biphenyl] -4-yl) -4- (3-chlorophenyl) -6-phenylpyrimidine (15.7 g, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 37.5 mmol), the same procedure as in Synthesis Example 139 was performed, to obtain 7-7 (14.3 g, yield 62%) of the title compound.
Mass (이론치: 675.84, 측정치: 676(M+H))Mass (Theoretical value: 675.84, Measured value: 676 (M + H))
[[
합성예Synthesis Example
146] 7-8의 합성 146] Synthesis of 7-8
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine (15.7 g, 37.5 mmol)을 사용하는 것을 제외하고는, 상기 합성예 139와 동일한 과정을 수행하여 목적 화합물인 7-8 (14.3 g, 수율 62%)을 얻었다.2- (3'-chloro- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 5-triazine (15.7 g, 37.5 mmol), to obtain the target compound 7-8 (14.3 g, yield 62%) was carried out in the same manner as in Synthesis Example 139.
Mass (이론치: 676.82, 측정치: 677(M+H))Mass (Theoretical value: 676.82, Measured value: 677 (M + H))
[[
합성예Synthesis Example
147] 7-9의 합성 147] Synthesis of 7-9
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine (15.7 g, 37.5 mmol)을 사용하는 것을 제외하고는, 상기 합성예 139와 동일한 과정을 수행하여 목적 화합물인 7-9 (14.3 g, 수율 62%)를 얻었다.2- (3'-chloro- [1,1'-biphenyl] -4-yl) -4,6-diphenyl-1,3, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 5-triazine (15.7 g, 37.5 mmol), to obtain the target compound 7-9 (14.3 g, yield 62%) was carried out in the same manner as in Synthesis Example 139.
Mass (이론치: 676.82, 측정치: 677(M+H))Mass (Theoretical value: 676.82, Measured value: 677 (M + H))
[[
합성예Synthesis Example
148] 7-10의 합성 148] Synthesis of 7-10
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(4'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine (15.7 g, 37.5 mmol)을 사용하는 것을 제외하고는, 상기 합성예 139와 동일한 과정을 수행하여 목적 화합물인 7-10 (14.3 g, 수율 62%)을 얻었다.2- (4'-chloro- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 5-triazine (15.7 g, 37.5 mmol), to obtain the target compound 7-10 (14.3 g, yield 62%) was carried out in the same manner as in Synthesis Example 139.
Mass (이론치: 676.82, 측정치: 677(M+H))Mass (Theoretical value: 676.82, Measured value: 677 (M + H))
[[
합성예Synthesis Example
149] 7-11의 합성 149] Synthesis of 7-11
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(4'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine (15.7 g, 37.5 mmol)을 사용하는 것을 제외하고는, 상기 합성예 139와 동일한 과정을 수행하여 목적 화합물인 7-11 (14.3 g, 수율 62%)을 얻었다.2- (4'-chloro- [1,1'-biphenyl] -4-yl) -4,6-diphenyl-1,3, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except that 5-triazine (15.7 g, 37.5 mmol) was used, the same procedure as in Synthesis Example 139 was performed, to obtain 7-11 (14.3 g, yield 62%) as a target compound.
Mass (이론치: 676.82, 측정치: 677(M+H))Mass (Theoretical value: 676.82, Measured value: 677 (M + H))
[[
합성예Synthesis Example
150] 7-12의 합성 150] Synthesis of 7-12
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-chloro-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine (13.4 g, 37.5 mmol)을 사용하는 것을 제외하고는, 상기 합성예 139와 동일한 과정을 수행하여 목적 화합물인 7-12 (12.8 g, 수율 61%)를 얻었다.2-chloro-4- (dibenzo [b, d] furan-4-yl) -6-phenyl-1,3,5-triazine (instead of 2-chloro-4,6-diphenyl-1,3,5-triazine) 13.4 g, 37.5 mmol) was obtained in the same manner as in Synthesis Example 139, to obtain 7-12 (12.8 g, yield 61%) of the title compound.
Mass (이론치: 614.71, 측정치: 615(M+H))Mass (Theoretical value: 614.71, Measured value: 615 (M + H))
[[
합성예Synthesis Example
151] 7-13의 합성 151] Synthesis of 7-13
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (13.4 g, 37.5 mmol)을 사용하는 것을 제외하고는, 상기 합성예 139와 동일한 과정을 수행하여 목적 화합물인 7-13 (12.8 g, 수율 61%)을 얻었다.2-chloro-4- (dibenzo [b, d] furan-3-yl) -6-phenyl-1,3,5-triazine (instead of 2-chloro-4,6-diphenyl-1,3,5-triazine) 13.4 g, 37.5 mmol) was obtained in the same manner as in Synthesis Example 139, to obtain 7-13 (12.8 g, 61% yield) of the title compound.
Mass (이론치: 614.71, 측정치: 615(M+H))Mass (Theoretical value: 614.71, Measured value: 615 (M + H))
[[
합성예Synthesis Example
152] 7-14의 합성 152] Synthesis of 7-14
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-chloro-4-(dibenzo[b,d]furan-2-yl)-6-phenyl-1,3,5-triazine (13.4 g, 37.5 mmol)을 사용하는 것을 제외하고는, 상기 합성예 139와 동일한 과정을 수행하여 목적 화합물인 7-14 (12.8 g, 수율 61%)를 얻었다.2-chloro-4- (dibenzo [b, d] furan-2-yl) -6-phenyl-1,3,5-triazine (instead of 2-chloro-4,6-diphenyl-1,3,5-triazine) 13.4 g, 37.5 mmol) was obtained in the same manner as in Synthesis Example 139, to obtain 7-14 (12.8 g, yield 61%) of the title compound.
Mass (이론치: 614.71, 측정치: 615(M+H))Mass (Theoretical value: 614.71, Measured value: 615 (M + H))
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합성예Synthesis Example
153] 7-15의 합성 153] Synthesis of 7-15
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-chloro-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine (13.4 g, 37.5 mmol)을 사용하는 것을 제외하고는, 상기 합성예 139와 동일한 과정을 수행하여 목적 화합물인 7-15 (12.8 g, 수율 61%)를 얻었다.2-chloro-4- (dibenzo [b, d] furan-1-yl) -6-phenyl-1,3,5-triazine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine ( Except for using 13.4 g, 37.5 mmol), the same procedure as in Synthesis Example 139 was performed, to obtain 7-15 (12.8 g, 61%) of the title compound.
Mass (이론치: 614.71, 측정치: 615(M+H))Mass (Theoretical value: 614.71, Measured value: 615 (M + H))
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합성예Synthesis Example
154] 7-16의 합성 154] Synthesis of 7-16
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3-chlorophenyl)-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine (16.3 g, 37.5 mmol)을 사용하는 것을 제외하고는, 상기 합성예 139와 동일한 과정을 수행하여 목적 화합물인 7-16 (13.7 g, 수율 58%)을 얻었다.2- (3-chlorophenyl) -4- (dibenzo [b, d] furan-4-yl) -6-phenyl-1,3, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 5-triazine (16.3 g, 37.5 mmol), the same procedure as in Synthesis Example 139 was performed to obtain 7-16 (13.7 g, yield 58%) as a target compound.
Mass (이론치: 690.81, 측정치: 691(M+H))Mass (Theoretical value: 690.81, Measured value: 691 (M + H))
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합성예Synthesis Example
155] 7-17의 합성 155] Synthesis of 7-17
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3-chlorophenyl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (16.3 g, 37.5 mmol)을 사용하는 것을 제외하고는, 상기 합성예 139와 동일한 과정을 수행하여 목적 화합물인 7-17 (13.7 g, 수율 58%)을 얻었다.2- (3-chlorophenyl) -4- (dibenzo [b, d] furan-3-yl) -6-phenyl-1,3, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except that 5-triazine (16.3 g, 37.5 mmol) was used, the same procedure as in Synthesis Example 139 was performed, to obtain 7-17 (13.7 g, yield 58%) of the title compound.
Mass (이론치: 690.81, 측정치: 691(M+H))Mass (Theoretical value: 690.81, Measured value: 691 (M + H))
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합성예Synthesis Example
156] 7-18의 합성 156] Synthesis of 7-18
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3-chlorophenyl)-4-(dibenzo[b,d]furan-2-yl)-6-phenyl-1,3,5-triazine (16.3 g, 37.5 mmol)을 사용하는 것을 제외하고는, 상기 합성예 139와 동일한 과정을 수행하여 목적 화합물인 7-18 (13.7 g, 수율 58%)을 얻었다.2- (3-chlorophenyl) -4- (dibenzo [b, d] furan-2-yl) -6-phenyl-1,3, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except that 5-triazine (16.3 g, 37.5 mmol) was used, the same procedure as in Synthesis Example 139 was performed, to obtain 7-18 (13.7 g, yield 58%) of the title compound.
Mass (이론치: 690.81, 측정치: 691(M+H))Mass (Theoretical value: 690.81, Measured value: 691 (M + H))
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합성예Synthesis Example
157] 7-19의 합성 157] Synthesis of 7-19
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3-chlorophenyl)-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine (16.3 g, 37.5 mmol)을 사용하는 것을 제외하고는, 상기 합성예 139와 동일한 과정을 수행하여 목적 화합물인 7-19 (13.7 g, 수율 58%)를 얻었다.2- (3-chlorophenyl) -4- (dibenzo [b, d] furan-1-yl) -6-phenyl-1,3, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except that 5-triazine (16.3 g, 37.5 mmol) was used, the same procedure as in Synthesis Example 139 was performed, to obtain 7-19 (13.7 g, yield 58%) of the title compound.
Mass (이론치: 690.81, 측정치: 691(M+H))Mass (Theoretical value: 690.81, Measured value: 691 (M + H))
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합성예Synthesis Example
158] 7-20의 합성 158] Synthesis of 7-20
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine (19.1 g, 37.5 mmol)을 사용하는 것을 제외하고는, 상기 합성예 139와 동일한 과정을 수행하여 목적 화합물인 7-20 (15.8 g, 수율 55%)을 얻었다.2- (3'-chloro- [1,1'-biphenyl] -3-yl) -4- (dibenzo [b, d] furan instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using 4-yl) -6-phenyl-1,3,5-triazine (19.1 g, 37.5 mmol), the same procedure as in Synthesis Example 139 was carried out to obtain the title compound 7-20 (15.8 g, yield 55%) was obtained.
Mass (이론치: 766.90, 측정치: 767(M+H))Mass (Theoretical value: 766.90, Measured value: 767 (M + H))
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합성예Synthesis Example
159] 7-21의 합성 159] Synthesis of 7-21
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (19.1 g, 37.5 mmol)을 사용하는 것을 제외하고는, 상기 합성예 139와 동일한 과정을 수행하여 목적 화합물인 7-21 (15.8 g, 수율 55%)을 얻었다.2- (3'-chloro- [1,1'-biphenyl] -3-yl) -4- (dibenzo [b, d] furan instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using -3-yl) -6-phenyl-1,3,5-triazine (19.1 g, 37.5 mmol), the same procedure as in Synthesis Example 139 was carried out to provide the title compound 7-21 (15.8). g, yield 55%) was obtained.
Mass (이론치: 766.90, 측정치: 767(M+H))Mass (Theoretical value: 766.90, Measured value: 767 (M + H))
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합성예Synthesis Example
160] 7-22의 합성 160] Synthesis of 7-22
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4-(dibenzo[b,d]furan-2-yl)-6-phenyl-1,3,5-triazine (19.1 g, 37.5 mmol)을 사용하는 것을 제외하고는, 상기 합성예 139와 동일한 과정을 수행하여 목적 화합물인 7-22 (15.8 g, 수율 55%)를 얻었다.2- (3'-chloro- [1,1'-biphenyl] -3-yl) -4- (dibenzo [b, d] furan instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using -2-yl) -6-phenyl-1,3,5-triazine (19.1 g, 37.5 mmol), the same procedure as in Synthesis Example 139 was carried out to obtain the title compound 7-22 (15.8). g, yield 55%) was obtained.
Mass (이론치: 766.90, 측정치: 767(M+H))Mass (Theoretical value: 766.90, Measured value: 767 (M + H))
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합성예Synthesis Example
161] 7-23의 합성 161] Synthesis of 7-23
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine (19.1 g, 37.5 mmol)을 사용하는 것을 제외하고는, 상기 합성예 139와 동일한 과정을 수행하여 목적 화합물인 7-23 (15.8 g, 수율 55%)을 얻었다.2- (3'-chloro- [1,1'-biphenyl] -3-yl) -4- (dibenzo [b, d] furan instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using -1-yl) -6-phenyl-1,3,5-triazine (19.1 g, 37.5 mmol), the same procedure as in Synthesis Example 139 was carried out to provide the title compound 7-23 (15.8). g, yield 55%) was obtained.
Mass (이론치: 766.90, 측정치: 767(M+H))Mass (Theoretical value: 766.90, Measured value: 767 (M + H))
[[
실시예Example
1 ~ 84] 녹색 유기 EL 소자의 제작 1 ~ 84] Fabrication of Green Organic EL Devices
합성예 1~161에서 합성한 화합물 1-1 ~ 화합물 7-23을 통상적으로 알려진 방법으로 고순도 승화정제를 한 후 아래의 과정에 따라 녹색 유기 EL 소자를 제작하였다.Compounds 1-1 to 7-23 synthesized in Synthesis Examples 1 to 161 were subjected to high purity sublimation purification by a conventionally known method, and then green organic EL devices were manufactured according to the following procedure.
먼저, ITO (Indium tin oxide)가 1500Å 두께로 박막 코팅된 유리 기판을증류수 초음파로 세척하였다. 증류수 세척이 끝나면 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고 건조시킨 후 UV OZONE 세정기 (Power sonic 405, 화신테크)로 이송시킨 다음 UV를 이용하여 상기 기판을 5분간 세정하고 진공 증착기로 기판을 이송하였다.First, a glass substrate coated with ITO (Indium tin oxide) having a thickness of 1500 Å was washed with distilled water ultrasonic waves. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc. is dried and transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech). The substrate was transferred to.
이렇게 준비된 ITO 투명 전극 위에 m-MTDATA (60 nm)/TCTA (80 nm)/ C-1 ~ C-228 의 각각의 화합물 + 10 % Ir(ppy)3 (30nm)/BCP (10 nm)/Alq3 (30 nm)/LiF (1 nm)/Al (200 nm) 순으로 적층하여 유기 EL 소자를 제작하였다. M-MTDATA (60 nm) / TCTA (80 nm) / C-1 to C-228 each compound + 10% Ir (ppy) 3 (30nm) / BCP (10 nm) / Alq on the thus prepared ITO transparent electrode An organic EL device was fabricated by stacking 3 (30 nm) / LiF (1 nm) / Al (200 nm) in this order.
m-MTDATA, TCTA, Ir(ppy)3, CBP 및 BCP의 구조는 하기와 같다.The structures of m-MTDATA, TCTA, Ir (ppy) 3 , CBP and BCP are as follows.
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비교예Comparative example
1] 녹색 유기 EL 소자의 제작 1] Fabrication of Green Organic EL Devices
발광층 형성시 발광 호스트 물질로서 화합물 1-1 대신 CBP를 사용하는 것을 제외하고는, 상기 실시예 1과 동일한 과정으로 녹색 유기 EL 소자를 제작하였다.A green organic EL device was manufactured in the same manner as in Example 1, except that CBP was used instead of Compound 1-1 as a light emitting host material when forming the emission layer.
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평가예Evaluation example
]]
실시예 1 ~ 84 및 비교예 1에서 제작한 각각의 녹색 유기 EL 소자에 대하여 전류밀도 (10) mA/㎠에서의 구동전압, 전류효율 및 발광 피크를 측정하고, 그 결과를 하기 표 1에 나타내었다.For each of the green organic EL devices produced in Examples 1 to 84 and Comparative Example 1, the driving voltage, current efficiency, and emission peak at current density (10) mA / cm 2 were measured, and the results are shown in Table 1 below. It was.
| 샘플Sample | 호스트Host | 구동 전압(V)Drive voltage (V) | EL 피크(nm)EL peak (nm) | 전류효율(cd/A)Current efficiency (cd / A) |
| 실시예 1Example 1 | 1-11-1 | 6.646.64 | 516516 | 42.242.2 |
| 실시예 2Example 2 | 1-21-2 | 6.356.35 | 517517 | 47.447.4 |
| 실시예 3Example 3 | 1-41-4 | 6.626.62 | 518518 | 49.249.2 |
| 실시예 4Example 4 | 1-71-7 | 6.536.53 | 516516 | 44.844.8 |
| 실시예 5Example 5 | 1-81-8 | 6.366.36 | 517517 | 43.143.1 |
| 실시예 6Example 6 | 1-101-10 | 6.886.88 | 516516 | 43.643.6 |
| 실시예 7Example 7 | 1-121-12 | 6.446.44 | 516516 | 47.447.4 |
| 실시예 8Example 8 | 1-141-14 | 6.626.62 | 516516 | 43.443.4 |
| 실시예 9Example 9 | 1-171-17 | 6.466.46 | 517517 | 49.249.2 |
| 실시예 10Example 10 | 1-191-19 | 6.396.39 | 516516 | 47.447.4 |
| 실시예 11Example 11 | 1-201-20 | 6.746.74 | 516516 | 47.647.6 |
| 실시예 12Example 12 | 1-221-22 | 6.816.81 | 518518 | 43.243.2 |
| 실시예 13Example 13 | 2-12-1 | 6.386.38 | 516516 | 47.447.4 |
| 실시예 14Example 14 | 2-22-2 | 6.546.54 | 518518 | 44.144.1 |
| 실시예 15Example 15 | 2-42-4 | 6.676.67 | 517517 | 42.442.4 |
| 실시예 16Example 16 | 2-72-7 | 6.326.32 | 517517 | 46.746.7 |
| 실시예 17Example 17 | 2-82-8 | 6.556.55 | 516516 | 44.844.8 |
| 실시예 18Example 18 | 2-102-10 | 6.836.83 | 518518 | 43.543.5 |
| 실시예 19Example 19 | 2-122-12 | 6.166.16 | 516516 | 48.148.1 |
| 실시예 20Example 20 | 2-142-14 | 6.246.24 | 516516 | 49.649.6 |
| 실시예 21Example 21 | 2-172-17 | 6.266.26 | 517517 | 49.949.9 |
| 실시예 22Example 22 | 2-192-19 | 6.186.18 | 518518 | 47.447.4 |
| 실시예 23Example 23 | 2-202-20 | 6.266.26 | 516516 | 49.249.2 |
| 실시예 24Example 24 | 2-222-22 | 6.126.12 | 517517 | 48.648.6 |
| 실시예 25Example 25 | 3-13-1 | 6.426.42 | 517517 | 49.449.4 |
| 실시예 26Example 26 | 3-23-2 | 6.476.47 | 518518 | 47.347.3 |
| 실시예 27Example 27 | 3-43-4 | 6.696.69 | 516516 | 47.447.4 |
| 실시예 28Example 28 | 3-73-7 | 6.346.34 | 516516 | 48.348.3 |
| 실시예 29Example 29 | 3-83-8 | 6.136.13 | 517517 | 43.443.4 |
| 실시예 30Example 30 | 3-103-10 | 6.226.22 | 516516 | 44.344.3 |
| 실시예 31Example 31 | 3-123-12 | 6.136.13 | 517517 | 46.346.3 |
| 실시예 32Example 32 | 3-143-14 | 6.646.64 | 516516 | 42.242.2 |
| 실시예 33Example 33 | 3-173-17 | 6.356.35 | 517517 | 47.447.4 |
| 실시예 34Example 34 | 3-193-19 | 6.626.62 | 518518 | 49.249.2 |
| 실시예 35Example 35 | 3-203-20 | 6.536.53 | 516516 | 44.844.8 |
| 실시예 36Example 36 | 3-223-22 | 6.366.36 | 517517 | 43.143.1 |
| 실시예 37Example 37 | 4-14-1 | 6.886.88 | 516516 | 43.643.6 |
| 실시예 38Example 38 | 4-24-2 | 6.446.44 | 516516 | 47.447.4 |
| 실시예 39Example 39 | 4-44-4 | 6.626.62 | 516516 | 43.443.4 |
| 실시예 40Example 40 | 4-74-7 | 6.466.46 | 517517 | 49.249.2 |
| 실시예 41Example 41 | 4-84-8 | 6.396.39 | 516516 | 47.447.4 |
| 실시예 42Example 42 | 4-104-10 | 6.746.74 | 516516 | 47.647.6 |
| 실시예 43Example 43 | 4-124-12 | 6.816.81 | 518518 | 43.243.2 |
| 실시예 44Example 44 | 4-144-14 | 6.386.38 | 516516 | 47.447.4 |
| 실시예 45Example 45 | 4-174-17 | 6.546.54 | 518518 | 44.144.1 |
| 실시예 46Example 46 | 4-194-19 | 6.676.67 | 517517 | 42.442.4 |
| 실시예 47Example 47 | 4-204-20 | 6.326.32 | 517517 | 46.746.7 |
| 실시예 48Example 48 | 4-224-22 | 6.556.55 | 516516 | 44.844.8 |
| 실시예 49Example 49 | 5-15-1 | 6.836.83 | 518518 | 43.543.5 |
| 실시예 50Example 50 | 5-25-2 | 6.166.16 | 516516 | 48.148.1 |
| 실시예 51Example 51 | 5-45-4 | 6.246.24 | 516516 | 49.649.6 |
| 실시예 52Example 52 | 5-75-7 | 6.266.26 | 517517 | 49.949.9 |
| 실시예 53Example 53 | 5-85-8 | 6.186.18 | 518518 | 47.447.4 |
| 실시예 54Example 54 | 5-105-10 | 6.266.26 | 516516 | 49.249.2 |
| 실시예 55Example 55 | 5-125-12 | 6.126.12 | 517517 | 48.648.6 |
| 실시예 56Example 56 | 5-145-14 | 6.426.42 | 517517 | 49.449.4 |
| 실시예 57Example 57 | 5-175-17 | 6.476.47 | 518518 | 47.347.3 |
| 실시예 58Example 58 | 5-195-19 | 6.696.69 | 516516 | 47.447.4 |
| 실시예 59Example 59 | 5-205-20 | 6.346.34 | 516516 | 48.348.3 |
| 실시예 60Example 60 | 5-225-22 | 6.136.13 | 517517 | 43.443.4 |
| 실시예 61Example 61 | 6-16-1 | 6.226.22 | 516516 | 44.344.3 |
| 실시예 62Example 62 | 6-26-2 | 6.136.13 | 517517 | 46.346.3 |
| 실시예 63Example 63 | 6-46-4 | 6.536.53 | 516516 | 44.844.8 |
| 실시예 64Example 64 | 6-76-7 | 6.366.36 | 517517 | 43.143.1 |
| 실시예 65Example 65 | 6-86-8 | 6.886.88 | 516516 | 43.643.6 |
| 실시예 66Example 66 | 6-106-10 | 6.446.44 | 516516 | 47.447.4 |
| 실시예 67Example 67 | 6-126-12 | 6.626.62 | 516516 | 43.443.4 |
| 실시예 68Example 68 | 6-146-14 | 6.466.46 | 517517 | 49.249.2 |
| 실시예 69Example 69 | 6-176-17 | 6.396.39 | 516516 | 47.447.4 |
| 실시예 70Example 70 | 6-196-19 | 6.746.74 | 516516 | 47.647.6 |
| 실시예 71Example 71 | 6-206-20 | 6.816.81 | 518518 | 43.243.2 |
| 실시예 72Example 72 | 6-226-22 | 6.386.38 | 516516 | 47.447.4 |
| 실시예 73Example 73 | 7-17-1 | 6.546.54 | 518518 | 44.144.1 |
| 실시예 74Example 74 | 7-27-2 | 6.676.67 | 517517 | 42.442.4 |
| 실시예 75Example 75 | 7-47-4 | 6.326.32 | 517517 | 46.746.7 |
| 실시예 76Example 76 | 7-77-7 | 6.556.55 | 516516 | 44.844.8 |
| 실시예 77Example 77 | 7-87-8 | 6.836.83 | 518518 | 43.543.5 |
| 실시예 78Example 78 | 7-107-10 | 6.366.36 | 517517 | 43.143.1 |
| 실시예 79Example 79 | 7-127-12 | 6.886.88 | 516516 | 43.643.6 |
| 실시예 80Example 80 | 7-147-14 | 6.446.44 | 516516 | 47.447.4 |
| 실시예 81Example 81 | 7-177-17 | 6.626.62 | 516516 | 43.443.4 |
| 실시예 82Example 82 | 7-197-19 | 6.466.46 | 517517 | 49.249.2 |
| 실시예 83Example 83 | 7-207-20 | 6.396.39 | 516516 | 47.447.4 |
| 실시예 84Example 84 | 7-227-22 | 6.746.74 | 516516 | 47.647.6 |
| 비교예 1Comparative Example 1 | CBPCBP | 6.93 6.93 | 516 516 | 38.2 38.2 |
상기 표 1에 나타낸 바와 같이, 본 발명에 따른 화합물 (1-1 ~ 7-23)을 녹색 유기 EL 소자의 발광층으로 사용하는 실시예 1~84의 녹색 유기 EL 소자는, 종래 CBP를 사용한 비교예 1의 녹색 유기 EL 소자와 비교해 볼 때 효율 및 구동전압 면에서 보다 우수한 성능을 나타내는 것을 알 수 있었다.As shown in Table 1, the green organic EL device of Examples 1 to 84 using the compound (1-1 to 7-23) according to the present invention as a light emitting layer of the green organic EL device is a comparative example using conventional CBP. Compared with the green organic EL device of 1, it was found to exhibit better performance in terms of efficiency and driving voltage.
Claims (8)
- 하기 화학식 1로 표시되는 화합물:Compound represented by the following formula (1):[화학식 1][Formula 1]
상기 화학식 1에서,In Chemical Formula 1,L1 및 L2는 서로 동일하거나 상이하며, 각각 독립적으로 단일결합이거나, 또는 C6~C18의 아릴렌기 및 핵원자수 5 내지 18개의 헤테로아릴렌기로 이루어진 군에서 선택되고,L 1 and L 2 are the same as or different from each other, and each independently a single bond, or a C 6 to C 18 arylene group and a nuclear atom having 5 to 18 heteroarylene groups, andAr1과 Ar2는 서로 동일하거나 또는 상이하며, Ar 1 and Ar 2 are the same as or different from each other,Ar1는 수소, 중수소(D), 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되고,Ar 1 is hydrogen, deuterium (D), halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 Cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, alkyloxy group of C 1 to C 40 , C 6 to C 60 Aryloxy group, C 1 to C 40 alkylsilyl group, C 6 to C 60 arylsilyl group, C 1 to C 40 alkyl boron group, C 6 to C 60 aryl boron group, C 6 to C 60 An aryl phosphine group, a C 6 -C 60 aryl phosphine oxide group and a C 6 -C 60 arylamine group,Ar2는 수소, 중수소(D), 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되고,Ar 2 is hydrogen, deuterium (D), halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, an aryl group of C 6 to C 60 , an alkyloxy group of C 1 to C 40 , an aryloxy group of C 6 to C 60 , and an alkyl of C 1 to C 40 Silyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 arylphosphine group, C 6 ~ C 60 aryl It is selected from the group consisting of a phosphine oxide group and C 6 ~ C 60 arylamine group,상기 L1 및 L2의 아릴렌기 및 헤테로아릴렌기와, 상기 Ar1 및 Ar2의 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기 및 아릴아민기는 각각 독립적으로 수소, 중수소(D), 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환될 수 있으며, 이때 상기 치환기가 복수인 경우, 이들은 서로 동일하거나 상이할 수 있다.The arylene group and heteroarylene group of L 1 and L 2 , the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryl jade of Ar 1 and Ar 2 The time period, alkylsilyl group, arylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and arylamine group are each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 of the alkynyl group, C 3 ~ C 40 cycloalkyl group, a nuclear atoms, 3 to 40 hetero cycloalkyl group, C 6 ~ C 60 the aryl group, the number of nuclear atoms aryl of from 5 to 60 heteroaryl group, a C 1 ~ C 40 alkyloxy group of, C 6 ~ aryloxy C 60, C 1 ~ C 40 alkyl silyl group, C 6 ~ C 60 aryl silyl group, C 1 ~ C 40 group of an alkyl boron, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 aryl phosphine oxide group, and a C 6 ~ of C 60 It may be substituted with 1 substituent selected from the group consisting of two or more amine groups, and the reel, wherein when the substituent is plural, they may be the same or different from each other. - 제1항에 있어서, The method of claim 1,Ar1과 Ar2는 서로 상이하며, Ar 1 and Ar 2 are different from each other,Ar1은 핵원자수 5 내지 19의 헤테로아릴기이며, Ar 1 is a heteroaryl group having 5 to 19 nuclear atoms,Ar2는 C6~C18의 아릴기이며, Ar 2 is an aryl group of C 6 ~ C 18 ,상기 Ar1과 Ar2의 아릴기와 헤테로아릴기는 각각 독립적으로 C6~C60의 아릴기 및 핵원자수 5 내지 60의 헤테로아릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 또는 비치환되는 것을 특징으로 하는 화합물. The aryl group and heteroaryl group of Ar 1 and Ar 2 are each independently substituted or unsubstituted with one or more substituents selected from the group consisting of C 6 ~ C 60 aryl group and a heteroaryl group of 5 to 60 nuclear atoms Characterized by a compound.
- 제1항에 있어서, The method of claim 1,상기 Ar1은 하기 화학식 2로 표시되는 치환체인 것인 화합물.The compound wherein Ar 1 is a substituent represented by the formula (2) below.[화학식 2][Formula 2]
상기 화학식 2에서,In Chemical Formula 2,*는 상기 화학식 1에 결합되는 부분을 의미하고,* Means a moiety bonded to Formula 1,Z1 내지 Z5는 서로 동일하거나 상이하며, 각각 독립적으로 N 또는 C(R1)이고, 다만 Z1 내지 Z5 중 적어도 하나는 N이고, 이때 R1이 복수인 경우, 복수의 R1은 서로 동일하거나 상이하고,Z 1 to Z 5 are the same as or different from each other, and each independently N or C (R 1 ), provided that at least one of Z 1 to Z 5 is N, wherein when R 1 is a plurality, a plurality of R 1 is Are the same or different from each other,R1는 수소, 중수소(D), 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 또는 인접하는 R1과 결합하여 축합 고리를 형성할 수 있고, R 1 is hydrogen, deuterium (D), halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 Cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, alkyloxy group of C 1 to C 40 , C 6 to C 60 Aryloxy group, C 1 to C 40 alkylsilyl group, C 6 to C 60 arylsilyl group, C 1 to C 40 alkyl boron group, C 6 to C 60 aryl boron group, C 6 to C 60 An aryl phosphine group, a C 6 ~ C 60 aryl phosphine oxide group and a C 6 ~ C 60 arylamine group, or may be combined with adjacent R 1 to form a condensed ring,상기 R1의 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기 및 아릴아민기는 각각 독립적으로 수소, 중수소(D), 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환될 수 있으며, 이때 상기 치환기가 복수인 경우, 이들은 서로 동일하거나 상이할 수 있다.Alkyl group of the R 1, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkyl boron group, an aryl boron group, The arylphosphine group, the arylphosphine oxide group and the arylamine group are each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 Alkynyl group of ˜C 40 , cycloalkyl group of C 3 ˜C 40 , heterocycloalkyl group of 3 to 40 nuclear atoms, aryl group of C 6 ˜C 60 , heteroaryl group of 5 to 60 nuclear atoms, C 1 ˜ C 40 alkyloxy group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ for C 60 aryl boron group, C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 aryl phosphine oxide group, and a C 6 ~ one or more substituents selected from the group consisting of an aryl amine of the C 60 of the It may be substituted, and wherein when the substituent is plural, they may be the same or different from each other. - 제3항에 있어서, The method of claim 3,상기 화학식 2로 표시되는 치환체는 하기 화학식 A-1 내지 A-15으로 구성되는 치환체 군에서 선택되는 것을 특징으로 하는 화합물:Substituent represented by the formula (2) is a compound, characterized in that selected from the group consisting of the following formula A-1 to A-15:
상기 A-1 내지 A-15에서,In the above A-1 to A-15,R1은 제3항에서 정의된 바와 같고,R 1 is as defined in claim 3,n은 0 내지 4의 정수로서, 상기 n이 1 내지 4의 정수인 경우, R2는 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40 60의 아릴옥시기 C1~C40의 알킬옥시기, C6~C40의 아릴아민기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C40의 아릴보론기, C6~C40의 아릴포스핀기, C6~C40의 아릴포스핀옥사이드기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택되거나, 또는 인접하는 기와 결합하여 축합 고리를 형성할 수 있으며,n is an integer of 0 to 4, when n is an integer of 1 to 4, R 2 is deuterium, halogen, cyano group, nitro group, C 1 -C 40 alkyl group, C 2 -C 40 alkenyl group, C an alkynyl group of 2 ~ C 40, C 3 ~ C 40 cycloalkyl group, the number of nuclear atoms of 3 to 40 hetero cycloalkyl, heteroaryl of C 6 ~ C 40 aryl group, the number of nuclear atoms of 5 to 40 aryl group, C 6 C 40 60 aryloxy group C 1 -C 40 alkyloxy group, C 6 -C 40 arylamine group, C 1 -C 40 alkylsilyl group, C 1 -C 40 alkylboron group, C 6 ~ C 40 aryl boron group, C 6 ~ C 40 aryl phosphine group, C 6 ~ C 40 aryl phosphine oxide group, and a C 6 ~ C 40 selected from an aryl silyl group the group consisting of or of, or adjacent groups of binding to the the To form condensed rings,상기 R2의 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C40의 아릴보론기, C6~C40의 아릴포스핀기, C6~C40의 아릴포스핀옥사이드기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환될 수 있으며, 이때 상기 치환기가 복수인 경우, 이들은 서로 동일하거나 상이할 수 있다.Alkyl group of the R 2, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, The arylphosphine group, the arylphosphine oxide group and the arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alky Neyl group, C 6 ~ C 40 aryl group, C 5 ~ C 40 heteroaryl group, C 6 ~ C 40 aryloxy group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 40 arylamine group, an aryl boronic of C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkyl silyl group, C 1 ~ C 40 group of an alkyl boron, C 6 ~ C 40 group, C 6 ~ C 40 aryl phosphine group, C 6 ~ C 40 aryl phosphine oxide group, and a C 6 ~ C 40 aryl silyl optionally substituted with one or more substituents selected from the group consisting of In this case, when the substituents are plural, they may be the same or different from each other. - 제1항에 있어서, The method of claim 1,상기 Ar1은 하기 화학식 3으로 표시되는 치환체인 것인 화합물: Ar 1 is a compound represented by Formula 3 below:[화학식 3][Formula 3]
상기 화학식 3에서,In Chemical Formula 3,*는 상기 화학식 1에 결합되는 부분을 의미하고,* Means a moiety bonded to Formula 1,Z는 서로 동일하거나 또는 상이하며, 각각 독립적으로 N 또는 C(R3)이고, 다만 복수의 Z 중 적어도 하나는 N이고, 이때 상기 R3이 복수인 경우, 이들은 서로 동일하거나 상이하며, Z is the same or different from each other, and each independently N or C (R 3 ), provided that at least one of the plurality of Z is N, wherein when R 3 is a plurality, they are the same or different from each other,X는 O 또는 S이며, X is O or S,R3 내지 R5는 서로 동일하거나 또는 상이하며, 각각 독립적으로 수소, 중수소(D), 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 또는 인접하는 기와 결합하여 축합 고리를 형성할 수 있고,R 3 to R 5 are the same or different and are each independently hydrogen, deuterium (D), a halogen, a cyano group, a nitro group, C 1 ~ alkenyl group of the C 40 alkyl group, C 2 ~ C 40 of, C 2 Alkynyl group of ˜C 40 , cycloalkyl group of C 3 ˜C 40 , heterocycloalkyl group of 3 to 40 nuclear atoms, aryl group of C 6 ˜C 60 , heteroaryl group of 5 to 60 nuclear atoms, C 1 ˜ C 40 alkyloxy group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ an aryl boronic of C 60, C 6 ~ C 60 aryl phosphine group, C 6 ~ aryl phosphine oxide of a C 60 group, and a C 6 ~, or selected from the group consisting of an aryl amine of the C 60, or adjacent groups combine to Can form condensed rings,n은 0 내지 7의 정수이고, n이 2 이상인 경우 복수의 R5는 서로 동일하거나 상이하며, n is an integer of 0 to 7, and when n is 2 or more, a plurality of R 5 are the same or different from each other,상기 R3 내지 R5에서 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기 및 아릴아민기는 각각 독립적으로 수소, 중수소(D), 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환될 수 있으며, 이때 상기 치환기가 복수인 경우, 이들은 서로 동일하거나 상이할 수 있다.Alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkyl boron group, aryl in the R 3 to R 5 boron group, an aryl phosphine group, aryl phosphine oxide group and an arylamine group each independently hydrogen, deuterium (D), a halogen, a cyano group, a nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group , C 2 ~ C 40 Alkynyl group, C 3 ~ C 40 Cycloalkyl group, C 3 ~ C 40 heterocycloalkyl group, C 6 ~ C 60 Aryl group, Nuclear atoms 5 to 60 heteroaryl group, C 1 -C 40 alkyloxy group, C 6 -C 60 aryloxy group, C 1 -C 40 alkylsilyl group, C 6 -C 60 arylsilyl group, C 1 -C 40 alkylboron group, aryl of C 6 ~ C 60 boron group, C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 aryl phosphine oxide group, and a C 6 ~ at least one selected from the group consisting of C 60 arylamine It may be substituted with a substituent, wherein when the substituent is plural, they may be the same or different from each other. - 제1항에 있어서, The method of claim 1,상기 Ar2은 페닐, 비페닐, 터페닐, 및 나프틸로 이루어진 군에서 선택되며, 상기 페닐, 비페닐, 터페닐, 나프틸은 각각 독립적으로 C6~C12의 아릴기로 치환되는 것을 특징으로 하는 화합물.Ar 2 is selected from the group consisting of phenyl, biphenyl, terphenyl, and naphthyl, wherein the phenyl, biphenyl, terphenyl, and naphthyl are each independently substituted with an aryl group having 6 to 12 carbon atoms. Compound.
- 양극, 음극 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하며, 상기 1층 이상의 유기물층 중 적어도 하나는 제1항 내지 제6항 중 어느 한 항에 기재된 화합물을 포함하는 유기 전계 발광 소자.An organic material comprising an anode, a cathode and at least one organic material layer interposed between the anode and the cathode, wherein at least one of the at least one organic material layer comprises the compound according to any one of claims 1 to 6. EL device.
- 제7항에 있어서, The method of claim 7, wherein상기 화합물을 포함하는 유기물층은 발광층, 전자 주입층, 발광보조층, 및 수명 개선층으로 구성된 군에서 선택되는 것을 특징으로 하는 유기 전계 발광 소자.The organic material layer comprising the compound is selected from the group consisting of a light emitting layer, an electron injection layer, a light emitting auxiliary layer, and a life improvement layer.
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