KR102673122B1 - Organic compound and organic electroluminescent device using the same - Google Patents
Organic compound and organic electroluminescent device using the same Download PDFInfo
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- KR102673122B1 KR102673122B1 KR1020160140359A KR20160140359A KR102673122B1 KR 102673122 B1 KR102673122 B1 KR 102673122B1 KR 1020160140359 A KR1020160140359 A KR 1020160140359A KR 20160140359 A KR20160140359 A KR 20160140359A KR 102673122 B1 KR102673122 B1 KR 102673122B1
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- 150000002894 organic compounds Chemical class 0.000 title abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 456
- 239000011368 organic material Substances 0.000 claims abstract description 22
- 239000010410 layer Substances 0.000 claims description 84
- 125000003118 aryl group Chemical group 0.000 claims description 38
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 125000004429 atom Chemical group 0.000 claims description 22
- 125000001424 substituent group Chemical group 0.000 claims description 22
- 125000001072 heteroaryl group Chemical group 0.000 claims description 17
- 238000002347 injection Methods 0.000 claims description 15
- 239000007924 injection Substances 0.000 claims description 15
- 230000005525 hole transport Effects 0.000 claims description 13
- 239000012044 organic layer Substances 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 229910052805 deuterium Inorganic materials 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 238000004020 luminiscence type Methods 0.000 abstract description 5
- 230000015572 biosynthetic process Effects 0.000 description 678
- 238000003786 synthesis reaction Methods 0.000 description 677
- 238000000034 method Methods 0.000 description 175
- 238000002360 preparation method Methods 0.000 description 73
- 239000000463 material Substances 0.000 description 41
- 238000005160 1H NMR spectroscopy Methods 0.000 description 40
- -1 metal complex compounds Chemical class 0.000 description 23
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 125000003003 spiro group Chemical group 0.000 description 17
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 125000004432 carbon atom Chemical group C* 0.000 description 14
- HUSSQXMWKXPRRF-UHFFFAOYSA-N [9-(4-phenylphenyl)carbazol-3-yl]boronic acid Chemical compound C12=CC=CC=C2C2=CC(B(O)O)=CC=C2N1C(C=C1)=CC=C1C1=CC=CC=C1 HUSSQXMWKXPRRF-UHFFFAOYSA-N 0.000 description 13
- BORLELIEOILAEA-UHFFFAOYSA-N [9-(4-phenylphenyl)carbazol-2-yl]boronic acid Chemical compound OB(O)C1=CC2=C(C=C1)C1=C(C=CC=C1)N2C1=CC=C(C=C1)C1=CC=CC=C1 BORLELIEOILAEA-UHFFFAOYSA-N 0.000 description 12
- ALTSSZFRWDVXPB-UHFFFAOYSA-N [9-(3-phenylphenyl)carbazol-3-yl]boronic acid Chemical compound C12=CC=CC=C2C2=CC(B(O)O)=CC=C2N1C(C=1)=CC=CC=1C1=CC=CC=C1 ALTSSZFRWDVXPB-UHFFFAOYSA-N 0.000 description 11
- 125000003545 alkoxy group Chemical group 0.000 description 11
- DBDCPKPHHCECLZ-UHFFFAOYSA-N 1-chloro-9h-carbazole Chemical compound N1C2=CC=CC=C2C2=C1C(Cl)=CC=C2 DBDCPKPHHCECLZ-UHFFFAOYSA-N 0.000 description 10
- LOQQFCPPDBFFSO-UHFFFAOYSA-N 2-chloro-9h-carbazole Chemical compound C1=CC=C2C3=CC=C(Cl)C=C3NC2=C1 LOQQFCPPDBFFSO-UHFFFAOYSA-N 0.000 description 10
- BKBSXIWYKWFQBX-UHFFFAOYSA-N 4-chloro-9h-carbazole Chemical compound N1C2=CC=CC=C2C2=C1C=CC=C2Cl BKBSXIWYKWFQBX-UHFFFAOYSA-N 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 125000000304 alkynyl group Chemical group 0.000 description 10
- 125000005264 aryl amine group Chemical group 0.000 description 10
- 125000004104 aryloxy group Chemical group 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- 125000000753 cycloalkyl group Chemical group 0.000 description 10
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 10
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 10
- 125000005103 alkyl silyl group Chemical group 0.000 description 9
- 125000005104 aryl silyl group Chemical group 0.000 description 9
- NFBOHOGPQUYFRF-UHFFFAOYSA-N oxanthrene Chemical group C1=CC=C2OC3=CC=CC=C3OC2=C1 NFBOHOGPQUYFRF-UHFFFAOYSA-N 0.000 description 9
- JMUUCLJHGLGNAP-UHFFFAOYSA-N [9-(3-phenylphenyl)carbazol-2-yl]boronic acid Chemical compound OB(O)C1=CC2=C(C=C1)C1=C(C=CC=C1)N2C1=CC=CC(=C1)C1=CC=CC=C1 JMUUCLJHGLGNAP-UHFFFAOYSA-N 0.000 description 8
- 125000003342 alkenyl group Chemical group 0.000 description 8
- 239000002019 doping agent Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- USKZJRMLKWTASM-UHFFFAOYSA-N C1(=CC=C(C=C1)N1C2=CC=CC=C2C=2C(=CC=CC1=2)B(O)O)C1=CC=CC=C1 Chemical compound C1(=CC=C(C=C1)N1C2=CC=CC=C2C=2C(=CC=CC1=2)B(O)O)C1=CC=CC=C1 USKZJRMLKWTASM-UHFFFAOYSA-N 0.000 description 6
- LKIKKGZECOPLRC-UHFFFAOYSA-N C1(=CC=C(C=C1)N1C2=CC=CC=C2C=2C=CC=C(C1=2)B(O)O)C1=CC=CC=C1 Chemical compound C1(=CC=C(C=C1)N1C2=CC=CC=C2C=2C=CC=C(C1=2)B(O)O)C1=CC=CC=C1 LKIKKGZECOPLRC-UHFFFAOYSA-N 0.000 description 6
- ZJOLCAGQDIAJHT-UHFFFAOYSA-N C1=C(C=CC=2C3=CC=CC=C3C3=CC=CC=C3C1=2)N1C2=CC=CC=C2C=2C=C(C=CC1=2)B(O)O Chemical compound C1=C(C=CC=2C3=CC=CC=C3C3=CC=CC=C3C1=2)N1C2=CC=CC=C2C=2C=C(C=CC1=2)B(O)O ZJOLCAGQDIAJHT-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- 125000004093 cyano group Chemical group *C#N 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 6
- 150000002367 halogens Chemical class 0.000 description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 6
- CMGJBMURTIQSQE-UHFFFAOYSA-N (9-naphthalen-1-ylcarbazol-3-yl)boronic acid Chemical compound C12=CC=CC=C2C2=CC(B(O)O)=CC=C2N1C1=CC=CC2=CC=CC=C12 CMGJBMURTIQSQE-UHFFFAOYSA-N 0.000 description 5
- CABSFELLEWZIAK-UHFFFAOYSA-N 3-chloro-9h-carbazole Chemical compound C1=CC=C2C3=CC(Cl)=CC=C3NC2=C1 CABSFELLEWZIAK-UHFFFAOYSA-N 0.000 description 5
- UUPOKUIKSKKEGY-UHFFFAOYSA-N C1=C(C=CC=2C3=CC=CC=C3C=CC1=2)N1C2=CC=CC=C2C=2C=C(C=CC1=2)B(O)O Chemical compound C1=C(C=CC=2C3=CC=CC=C3C=CC1=2)N1C2=CC=CC=C2C=2C=C(C=CC1=2)B(O)O UUPOKUIKSKKEGY-UHFFFAOYSA-N 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- PZSRTZBJMZCSES-UHFFFAOYSA-N (9-naphthalen-2-ylcarbazol-2-yl)boronic acid Chemical compound OB(O)C1=CC2=C(C=C1)C1=CC=CC=C1N2C1=CC2=C(C=CC=C2)C=C1 PZSRTZBJMZCSES-UHFFFAOYSA-N 0.000 description 4
- QPLYXWYRHWNPAH-UHFFFAOYSA-N C1(=CC=CC2=CC=CC=C12)N1C2=CC=CC=C2C=2C=CC(=CC1=2)B(O)O Chemical compound C1(=CC=CC2=CC=CC=C12)N1C2=CC=CC=C2C=2C=CC(=CC1=2)B(O)O QPLYXWYRHWNPAH-UHFFFAOYSA-N 0.000 description 4
- ZPUZVKYNAUJBQW-UHFFFAOYSA-N C1(=CC=CC=C1)C1=CC(=CC(=C1)N1C2=CC=CC=C2C=2C=C(C=CC1=2)B(O)O)C1=CC=CC=C1 Chemical compound C1(=CC=CC=C1)C1=CC(=CC(=C1)N1C2=CC=CC=C2C=2C=C(C=CC1=2)B(O)O)C1=CC=CC=C1 ZPUZVKYNAUJBQW-UHFFFAOYSA-N 0.000 description 4
- AGVHXSDXWFQHCP-UHFFFAOYSA-N C1=C(C=CC=2C3=CC=CC=C3C=CC1=2)N1C2=CC=CC=C2C=2C=CC(=CC1=2)B(O)O Chemical compound C1=C(C=CC=2C3=CC=CC=C3C=CC1=2)N1C2=CC=CC=C2C=2C=CC(=CC1=2)B(O)O AGVHXSDXWFQHCP-UHFFFAOYSA-N 0.000 description 4
- SGYMFBRERFOSTE-UHFFFAOYSA-N OB(O)C1=CC=C2C(=C1)N(C1=C2C=CC=C1)C1=CC=C2C(=C1)C1=C(C=CC=C1)C1=C2C=CC=C1 Chemical compound OB(O)C1=CC=C2C(=C1)N(C1=C2C=CC=C1)C1=CC=C2C(=C1)C1=C(C=CC=C1)C1=C2C=CC=C1 SGYMFBRERFOSTE-UHFFFAOYSA-N 0.000 description 4
- XNTIRYHJAOMLQZ-UHFFFAOYSA-N OB(O)C1=CC=CC2=C1C1=C(C=CC=C1)N2C1=CC=CC(=C1)C1=CC=CC=C1 Chemical compound OB(O)C1=CC=CC2=C1C1=C(C=CC=C1)N2C1=CC=CC(=C1)C1=CC=CC=C1 XNTIRYHJAOMLQZ-UHFFFAOYSA-N 0.000 description 4
- LLUFNEMYJVNSDZ-UHFFFAOYSA-N OB(O)C1=CC=CC2=C1N(C1=C2C=CC=C1)C1=CC=CC(=C1)C1=CC=CC=C1 Chemical compound OB(O)C1=CC=CC2=C1N(C1=C2C=CC=C1)C1=CC=CC(=C1)C1=CC=CC=C1 LLUFNEMYJVNSDZ-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- YQDDAXFSQPAUCR-UHFFFAOYSA-N [9-(3,5-diphenylphenyl)carbazol-2-yl]boronic acid Chemical compound OB(O)C1=CC2=C(C=C1)C1=C(C=CC=C1)N2C1=CC(=CC(=C1)C1=CC=CC=C1)C1=CC=CC=C1 YQDDAXFSQPAUCR-UHFFFAOYSA-N 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- 238000011161 development Methods 0.000 description 4
- 230000005684 electric field Effects 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- NJKCFLBYPCPLOS-UHFFFAOYSA-N (9-naphthalen-2-ylcarbazol-3-yl)boronic acid Chemical compound C12=CC=CC=C2C2=CC(B(O)O)=CC=C2N1C1=CC=C(C=CC=C2)C2=C1 NJKCFLBYPCPLOS-UHFFFAOYSA-N 0.000 description 3
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 3
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 2
- ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 description 2
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 2
- ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 description 2
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 2
- IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 description 2
- YJLIKUSWRSEPSM-WGQQHEPDSA-N (2r,3r,4s,5r)-2-[6-amino-8-[(4-phenylphenyl)methylamino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1CNC1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O YJLIKUSWRSEPSM-WGQQHEPDSA-N 0.000 description 2
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 2
- UDQTXCHQKHIQMH-KYGLGHNPSA-N (3ar,5s,6s,7r,7ar)-5-(difluoromethyl)-2-(ethylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazole-6,7-diol Chemical compound S1C(NCC)=N[C@H]2[C@@H]1O[C@H](C(F)F)[C@@H](O)[C@@H]2O UDQTXCHQKHIQMH-KYGLGHNPSA-N 0.000 description 2
- OOKAZRDERJMRCJ-KOUAFAAESA-N (3r)-7-[(1s,2s,4ar,6s,8s)-2,6-dimethyl-8-[(2s)-2-methylbutanoyl]oxy-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-3-hydroxy-5-oxoheptanoic acid Chemical compound C1=C[C@H](C)[C@H](CCC(=O)C[C@@H](O)CC(O)=O)C2[C@@H](OC(=O)[C@@H](C)CC)C[C@@H](C)C[C@@H]21 OOKAZRDERJMRCJ-KOUAFAAESA-N 0.000 description 2
- HUWSZNZAROKDRZ-RRLWZMAJSA-N (3r,4r)-3-azaniumyl-5-[[(2s,3r)-1-[(2s)-2,3-dicarboxypyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-5-oxo-4-sulfanylpentane-1-sulfonate Chemical compound OS(=O)(=O)CC[C@@H](N)[C@@H](S)C(=O)N[C@@H]([C@H](C)CC)C(=O)N1CCC(C(O)=O)[C@H]1C(O)=O HUWSZNZAROKDRZ-RRLWZMAJSA-N 0.000 description 2
- MPDDTAJMJCESGV-CTUHWIOQSA-M (3r,5r)-7-[2-(4-fluorophenyl)-5-[methyl-[(1r)-1-phenylethyl]carbamoyl]-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoate Chemical compound C1([C@@H](C)N(C)C(=O)C2=NN(C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C2C(C)C)C=2C=CC(F)=CC=2)=CC=CC=C1 MPDDTAJMJCESGV-CTUHWIOQSA-M 0.000 description 2
- MAYZWDRUFKUGGP-VIFPVBQESA-N (3s)-1-[5-tert-butyl-3-[(1-methyltetrazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound CN1N=NN=C1CN1C2=NC(C(C)(C)C)=NC(N3C[C@@H](O)CC3)=C2N=N1 MAYZWDRUFKUGGP-VIFPVBQESA-N 0.000 description 2
- IIJJRVDUWAQIGT-UHFFFAOYSA-N (9-naphthalen-1-ylcarbazol-4-yl)boronic acid Chemical compound C1(=CC=CC2=CC=CC=C12)N1C2=CC=CC=C2C=2C(=CC=CC1=2)B(O)O IIJJRVDUWAQIGT-UHFFFAOYSA-N 0.000 description 2
- UKGJZDSUJSPAJL-YPUOHESYSA-N (e)-n-[(1r)-1-[3,5-difluoro-4-(methanesulfonamido)phenyl]ethyl]-3-[2-propyl-6-(trifluoromethyl)pyridin-3-yl]prop-2-enamide Chemical compound CCCC1=NC(C(F)(F)F)=CC=C1\C=C\C(=O)N[C@H](C)C1=CC(F)=C(NS(C)(=O)=O)C(F)=C1 UKGJZDSUJSPAJL-YPUOHESYSA-N 0.000 description 2
- ZGYIXVSQHOKQRZ-COIATFDQSA-N (e)-n-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]-3-cyano-7-[(3s)-oxolan-3-yl]oxyquinolin-6-yl]-4-(dimethylamino)but-2-enamide Chemical compound N#CC1=CN=C2C=C(O[C@@H]3COCC3)C(NC(=O)/C=C/CN(C)C)=CC2=C1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 ZGYIXVSQHOKQRZ-COIATFDQSA-N 0.000 description 2
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- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 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
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 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
- 239000011133 lead Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 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
- 239000000203 mixture Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 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
- 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
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 238000011160 research Methods 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
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- GVIJJXMXTUZIOD-UHFFFAOYSA-N thianthrene Chemical compound C1=CC=C2SC3=CC=CC=C3SC2=C1 GVIJJXMXTUZIOD-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 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
- 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
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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Abstract
본 발명은 신규한 유기 화합물 및 이를 이용한 유기 전계 발광 소자에 관한 것으로, 보다 상세하게는 발광능이 우수한 신규 화합물 및 이를 하나 이상의 유기물층에 포함함으로써, 높은 발광효율, 낮은 구동전압, 긴 수명 등의 특성이 향상된 유기 전계 발광 소자에 관한 것이다.The present invention relates to a novel organic compound and an organic electroluminescent device using the same. More specifically, a novel compound with excellent luminescence performance and its inclusion in one or more organic material layers provide characteristics such as high luminous efficiency, low driving voltage, and long lifespan. It relates to improved organic electroluminescent devices.
Description
본 발명은 신규한 유기 화합물 및 이를 이용한 유기 전계 발광 소자에 관한 것으로, 보다 상세하게는 발광능이 우수한 화합물 및 이를 하나 이상의 유기물층에 포함함으로써, 발광효율, 구동전압, 수명 등의 특성이 향상된 유기 전계 발광 소자에 관한 것이다.The present invention relates to a novel organic compound and an organic electroluminescent device using the same, and more specifically, to a compound with excellent luminescence performance and its inclusion in one or more organic material layers, thereby improving organic electroluminescence properties such as luminous efficiency, driving voltage, and lifespan. It's about elements.
1950년대 Bernanose의 유기 박막 발광 관측을 시점으로 1965년 안트라센 단결정을 이용한 청색 전기발광으로 이어진 유기 전계 발광(electroluminescent) 소자에 대한 연구는 1987년 탕(Tang)에 의하여 정공층과 발광층의 기능층으로 나눈 적층구조의 유기 전계 발광 소자가 제시되었다. 이후, 고효율, 고수명의 유기 전계 발광 소자를 만들기 위하여, 소자 내 각각의 특징적인 유기물층을 도입하는 형태로 발전하여 왔으며, 이에 사용되는 특화된 물질의 개발로 이어졌다.Beginning with Bernanose's observation of organic thin film luminescence in the 1950s, research on organic electroluminescent devices, which led to blue electroluminescence using anthracene single crystals in 1965, was divided into a functional layer of a hole layer and a light emitting layer by Tang in 1987. An organic electroluminescent device with a layered structure was presented. Since then, in order to create high-efficiency, long-life organic electroluminescent devices, there has been development in the form of introducing each characteristic organic material layer within the device, leading to the development of specialized materials used for this.
유기 전계 발광 소자에서는 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 an organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected from the anode and electrons are injected from the cathode into the organic material layer. When the injected hole and electron meet, an exciton is formed, and when this exciton falls to the ground state, light is emitted. At this time, the material used as the organic material layer can be classified into light-emitting material, hole injection material, hole transport material, electron transport material, electron injection material, etc., depending on its function.
유기 전계 발광 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.Materials for forming the light-emitting layer of an organic electroluminescent device can be classified into blue, green, and red light-emitting materials depending on the color of the light. In addition, yellow and orange luminescent materials are also used as luminescent materials to realize better natural colors. Additionally, in order to increase color purity and increase luminous efficiency through energy transfer, a host/dopant system can be used as a luminescent material.
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.Dopant materials can be divided into fluorescent dopants using organic materials and phosphorescent dopants using metal complex compounds containing heavy atoms such as Ir and Pt. The development of these phosphorescent materials can theoretically improve luminous efficiency by up to 4 times compared to fluorescence, so interest is focused on not only phosphorescent dopants but also phosphorescent host materials.
현재까지 정공 주입층, 정공 수송층. 정공 차단층, 전자 수송층으로 사용되는 물질은, 하기 화학식으로 표현된 NPB, BCP, Alq3 등이 널리 알려져 있고, 발광 물질로는 안트라센 유도체들이 형광 도판트/호스트 재료로서 보고되고 있다. 특히 발광재료 중 효율 향상 측면에서 큰 장점을 가지고 있는 인광 도펀트 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.So far, hole injection layer and hole transport layer. Materials used as hole blocking layers and electron transport layers are widely known, such as NPB, BCP, and Alq 3 expressed by the following chemical formula, and as light-emitting materials, anthracene derivatives have been reported as fluorescent dopant/host materials. In particular, among light emitting materials, phosphorescent dopant materials that have great advantages in terms of efficiency improvement include metal complex compounds containing Ir such as Firpic, Ir(ppy) 3 , (acac)Ir(btp) 2 , etc., which produce blue, green, and red dopants. It is used as a material. To date, CBP has shown excellent properties as a phosphorescent host material.
그러나, 종래 발광 물질들은 발광 특성 측면에서는 유리한 면이 있으나, 유리전이온도가 낮고 열적 안정성이 매우 좋지 않기 때문에, 유기 전계 발광 소자에서의 수명 측면에서 만족할만한 수준이 되지 못하고 있다. 따라서, 우수한 성능을 가지는 발광 물질의 개발이 요구되고 있다.However, although conventional light-emitting materials have advantages in terms of light-emitting properties, their glass transition temperature is low and thermal stability is very poor, so they are not at a satisfactory level in terms of lifespan in organic electroluminescent devices. Therefore, there is a demand for the development of light-emitting materials with excellent performance.
상기한 문제점을 해결하기 위해, 본 발명은 유기 전계 발광 소자에 적용할 수 있으며, 발광능이 우수한 신규 유기 화합물을 제공하는 것을 목적으로 한다.In order to solve the above problems, the present invention aims to provide a new organic compound that can be applied to organic electroluminescent devices and has excellent luminescent performance.
또한, 본 발명은 상기 신규 유기 화합물을 포함하여 낮은 구동전압과 높은 발광효율을 나타내며 수명이 향상되는 유기 전계 발광 소자를 제공하는 것을 또 다른 목적으로 한다.Another object of the present invention is to provide an organic electroluminescent device that includes the novel organic compound, exhibits low driving voltage, high luminous efficiency, and has improved lifespan.
상기 목적을 달성하기 위하여, 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).
[화학식 1][Formula 1]
상기 화학식 1에서,In Formula 1,
Ar1은 하기 화학식 2 또는 화학식 3으로 표시되는 치환체이고,Ar 1 is a substituent represented by Formula 2 or Formula 3 below,
Ar2는 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 선택되며, 이때 Ar2가 C6~C60의 아릴기 또는 핵원자수 5 내지 60의 헤테로아릴기일 경우, 상기 Ar1과 동일하거나 상이하고,Ar 2 is 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, number of nuclear atoms is 3 Heterocycloalkyl group of 40 to 40, C 6 to C 60 aryl group, heteroaryl group of 5 to 60 nuclear atoms, C 1 to C 40 alkyloxy group, C 6 to C 60 aryloxy group, C 1 to C 40 alkylsilyl 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 ~ It is selected from the group consisting of a C 60 arylphosphine oxide group and a C 6 ~ C 60 arylamine group, wherein when Ar 2 is a C 6 ~ C 60 aryl group or a heteroaryl group with 5 to 60 nuclear atoms, the above Same as or different from Ar 1 ,
[화학식 2][Formula 2]
[화학식 3][Formula 3]
상기 화학식 2 및 3에서,In Formulas 2 and 3,
* 는 상기 화학식 1과 결합하는 부위를 나타내고,* represents the site that binds to Formula 1 above,
X1 내지 X3는 C(R1)(R2), O, S 및 N(R3)로 이루어진 군에서 선택되고, X 1 to X 3 are selected from the group consisting of C(R 1 )(R 2 ), O, S and N(R 3 ),
R1 내지 R3는 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, 혹은 인접하는 기와 결합하여 축합 고리를 형성할 수 있고,R 1 to R 3 are the same or different from each other, and each independently represents hydrogen, deuterium (D), halogen, cyano group, nitro group, 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, heterocycloalkyl group with 3 to 40 nuclear atoms, C 6 to C 60 aryl group, heteroaryl group with 5 to 60 nuclear atoms, C 1 to 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 Selected from the group consisting of an aryl boron group of 60 , an arylphosphine group of C 6 ~ C 60 , an arylphosphine oxide group of C 6 ~ C 60 , and an arylamine group of C 6 ~ C 60 , or condensed by combining with an adjacent group can form a ring,
상기 Ar2, R1 내지 R3의 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기 및 아릴아민기는 각각 독립적으로 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.Ar 2 , R 1 to R 3 alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and aryl amine group are each independently selected from deuterium (D), halogen, cyano group, nitro group, C 1 to C 40 alkyl group, C 2 to C 40 alkene. Nyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C 6 to C 60 aryl group, heteroaryl group with 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 ~ C 60 aryl boron group, C 6 ~ C 60 arylphosphine group, C 6 ~ C 60 arylphosphine oxide group, and C 6 ~ C 60 one or more substituents selected from the group consisting of arylamine group may be substituted, and in this case, when the substituents are plural, they may be the same or different from each other.
또한, 본 발명은 양극, 음극 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하고, 상기 1층 이상의 유기물층 중 적어도 하나는 상기 화학식 1로 표시되는 화합물을 포함하는 것인 유기 전계 발광 소자를 제공한다. 여기서, 상기 화학식 1로 표시되는 화합물을 포함하는 유기물층은 정공 주입층, 정공 수송층, 발광 보조층, 발광층, 전자 수송층 및 전자 주입층으로 이루어진 군에서 선택될 수 있다. 이때, 상기 화학식 1로 표시되는 화합물은 발광층의 인광 호스트로 사용될 수 있다. In addition, the present invention provides an organic material comprising 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 the compound represented by Formula 1 above. An electroluminescent device is provided. Here, the organic material layer containing the compound represented by Formula 1 may be selected from the group consisting of a hole injection layer, a hole transport layer, an auxiliary light emitting layer, a light emitting layer, an electron transport layer, and an electron injection layer. At this time, the compound represented by Formula 1 may be used as a phosphorescent host of the light-emitting layer.
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 has excellent thermal stability and luminescence properties, so it can be used as a material for the organic layer of an organic electroluminescent device.
특히, 본 발명의 화학식 1로 표시되는 화합물을 인광 호스트 재료로 사용할 경우, 종래의 호스트 재료에 비해 낮은 구동전압, 높은 효율 및 긴 수명을 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 with low driving voltage, high efficiency, and long lifespan can be manufactured compared to conventional host materials, and further improves performance and lifespan. This improved full-color display panel can also be manufactured.
이하, 본 발명을 상세히 설명한다.Hereinafter, the present invention will be described in detail.
1. 신규 유기 화합물1. Novel organic compounds
본 발명에 따른 신규 유기 화합물은 '비스카바졸 모이어티'에 '스파이로 모이어티'가 결합되거나, 또는 '비스카바졸 모이어티'에 '디벤조다이옥신 모이어티'이 직접 결합된 구조를 기본 골격으로 하며, 이러한 기본 골격에 다양한 치환기가 도입되어 상기 화학식 1로 표시되는 것을 특징으로 한다. 상기 스파이로 모이어티는 스파이로(안트라센-플루오렌), 스파이로(플루오렌-크산텐), 스파이로(플루오렌-티오크산텐), 스파이로(아크리딘-플루오렌) 등일 수 있고, 상기 디벤조다이옥신 모이어티는 디하이드로안트라센, 디벤조다이옥신, 티안트렌, 페나진 등일 수 있다.The new organic compound according to the present invention has a basic structure in which a 'spiro moiety' is bonded to a 'biscarbazole moiety' or a 'dibenzodioxin moiety' is directly bonded to a 'biscarbazole moiety'. It is characterized in that various substituents are introduced into this basic skeleton and are represented by the above formula (1). The spiro moiety may be spiro (anthracene-fluorene), spiro (fluorene-xanthene), spiro (fluorene-thioxanthene), spiro (acridine-fluorene), etc., The dibenzodioxin moiety may be dihydroanthracene, dibenzodioxin, thiantrene, phenazine, etc.
구체적으로, 상기 화학식 1의 화합물은 열적 안정성과 정공 수송 능력이 우수한 '비스카바졸 모이어티'와 '스파이로 모이어티/디벤조다이옥신 모이어티'를 포함한다. 이러한 화학식 1의 화합물을 유기 전계 발광 소자의 발광층에 사용할 경우에는 정공 수송층을 통해 발광층으로 들어오는 정공을 수용하는 능력이 우수하여, 발광층 내에서 정공과 전자가 결합할 수 있는 확률을 향상시킬 수 있다.Specifically, the compound of Formula 1 includes a 'biscarbazole moiety' and a 'spiro moiety/dibenzodioxin moiety' that have excellent thermal stability and hole transport ability. When the compound of Formula 1 is used in the light-emitting layer of an organic electroluminescent device, it has an excellent ability to accommodate holes entering the light-emitting layer through the hole transport layer, thereby improving the probability that holes and electrons can combine in the light-emitting layer.
또한, 상기 화학식 1의 화합물은 비스카바졸 모이어티에 스파이로 모이어티가 결합됨으로써 입체 장애가 형성되어 필름 형성시 발생하는 결정화를 방지하고, 높은 열 안정성을 유지하여 높은 증착온도에도 안정한 효과를 나타낼 수 있다. 이러한 화학식 1의 화합물을 유기 전계 발광 소자의 발광층에 사용할 경우에는 소자의 수명이 연장되어 장시간 사용할 수 있다(하기 표 1 참조). 이때, 상기 화학식 1의 헤테로원자(N, O, S) 함유 스파이로 모이어티는 양쪽성(amphiprotic)을 가지므로, 헤테로원자를 함유하지 않는 스파이로 모이어티(예컨대, 스파이로비플루오렌)에 비해 p-type 효과가 강화될 수 있다. 이러한 헤테로원자 함유 스파이로 모이어티를 포함하는 화합물을 p-type으로 사용할 경우에는 정공(hole) 특성이 강화되어, 정공 수송층으로부터 정공을 잘 수용할 수 있다.In addition, the compound of Formula 1 forms steric hindrance by binding the spiro moiety to the biscarbazole moiety, preventing crystallization that occurs during film formation, and maintains high thermal stability, showing a stable effect even at high deposition temperatures. . When the compound of Formula 1 is used in the light-emitting layer of an organic electroluminescent device, the lifespan of the device is extended and it can be used for a long time (see Table 1 below). At this time, the heteroatom (N, O, S)-containing spiro moiety of Formula 1 is amphiprotic, so compared to the spiro moiety (e.g., spirobifluorene) that does not contain heteroatoms. The p-type effect may be strengthened. When a compound containing such a heteroatom-containing spiro moiety is used as a p-type, hole characteristics are strengthened and holes can be easily accommodated from the hole transport layer.
또한, 상기 화학식 1의 화합물은 비스카바졸 모이어티에 디벤조다이옥신 모이어티가 결합됨으로써 정공(hole) 특성이 향상되어 p-type 특성을 보다 강화시킬 수 있다. 이러한 화학식 1의 화합물을 유기 전계 발광 소자의 발광층에 사용할 경우에는 강한 p-type 특성에 의해 정공 수송층으로부터 정공을 수용하는 능력이 향상되어, 발광층 내 정공(hole)과 전자(electron)가 결합될 확률을 높여 저전압, 고효율 효과를 나타낼 수 있다. 이때, 상기 화학식 1의 비스카바졸 모이어티에 디벤조다이옥신 모이어티가 결합된 화합물은 HOMO가 비스카바졸에, LUMO가 디벤조다이옥신에 집중적으로 분포하여 효과적으로 화합물 내 전하 균형(charge blance)을 이룰 수 있다.In addition, the compound of Formula 1 has improved hole characteristics by combining the dibenzodioxin moiety with the biscarbazole moiety, thereby further strengthening the p-type characteristics. When the compound of Formula 1 is used in the light-emitting layer of an organic electroluminescent device, the ability to accept holes from the hole transport layer is improved due to its strong p-type characteristics, thereby increasing the probability of combining holes and electrons in the light-emitting layer. By increasing , low voltage and high efficiency effects can be achieved. At this time, in the compound in which the dibenzodioxin moiety is bound to the biscarbazole moiety of Formula 1, the HOMO is concentrated in the biscarbazole and the LUMO is concentrated in the dibenzodioxin, thereby effectively achieving charge balance within the compound. there is.
또한, 상기 화학식 1의 화합물은 상기 기본 골격에 도입되는 다양한 치환기의 종류에 따라 HOMO 및 LUMO 에너지 레벨을 조절할 수 있으며, 넓은 밴드 갭뿐만 아니라 우수한 정공 수송성을 가질 수 있다. 이러한 화학식 1의 화합물은 상기 기본 골격에 방향족환 및/또는 질소-함유 헤테로환이 결합되어 유기 전계 발광 소자의 유기물층 재료, 특히 발광층 재료로 사용될 수 있다.In addition, the compound of Formula 1 can control HOMO and LUMO energy levels depending on the types of various substituents introduced into the basic skeleton, and can have not only a wide band gap but also excellent hole transport properties. The compound of Formula 1 has an aromatic ring and/or a nitrogen-containing heterocycle bonded to the basic skeleton and can be used as an organic layer material, especially a light-emitting layer material, of an organic electroluminescent device.
이와 같은 화학식 1로 표시되는 화합물은 종래 유기 전계 발광 소자용 재료[예: 4,4-dicarbazolybiphenyl (이하, ‘CBP’라 함)]에 비해 높은 분자량을 갖기 때문에, 유리전이온도가 높아 열적 안정성이 우수할 뿐만 아니라 발광능이 우수하다. 따라서, 상기 화학식 1의 화합물을 유기 전계 발광 소자의 유기물층에 적용할 경우에는 소자의 구동전압, 효율, 수명 등이 향상될 수 있다. 이러한 화학식 1의 화합물은 유기 전계 발광 소자의 유기물층 재료로 사용될 수 있으며, 바람직하게는 발광층 재료(녹색의 인광 호스트 재료)로 사용될 수 있다.The compound represented by Formula 1 has a higher molecular weight than conventional materials for organic electroluminescent devices (e.g., 4,4-dicarbazolybiphenyl (hereinafter referred to as 'CBP')), so it has a high glass transition temperature and thermal stability. Not only is it excellent, but its luminous ability is also excellent. Therefore, when the compound of Formula 1 is applied to the organic material layer of an organic electroluminescent device, the driving voltage, efficiency, lifespan, etc. of the device can be improved. The compound of Formula 1 can be used as an organic layer material of an organic electroluminescent device, and preferably as a light-emitting layer material (green phosphorescent host material).
따라서, 본 발명에 따른 화학식 1의 화합물을 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.Therefore, the performance and lifespan characteristics of the organic electroluminescent device containing the compound of Formula 1 according to the present invention can be greatly improved, and the performance of a full-color organic light emitting panel to which such an organic electroluminescent device is applied can also be maximized.
본 발명에 따른 신규 화합물은 비스카바졸 모이어티에 스파이로 모이어티 또는 디벤조다이옥신 모이어티가 직접 결합되면서 다양한 치환기가 도입되는 것으로, 상기 화학식 1로 표시된다.The new compound according to the present invention is represented by the above formula (1) in which various substituents are introduced by directly bonding a spiro moiety or a dibenzodioxin moiety to a biscarbazole moiety.
구체적으로, 상기 화학식 1로 표시되는 화합물은 두 개의 카바졸이 벤젠 고리를 통해 직접 연결된 비스카바졸 모이어티를 기본 골격으로 포함한다. 이러한 화학식 1의 화합물은 하기 화학식 4 내지 7 중 적어도 어느 하나로 구체화될 수 있다. 그러나, 이에 특별히 한정되지 않는다.Specifically, the compound represented by Formula 1 includes a biscarbazole moiety in which two carbazoles are directly linked through a benzene ring as a basic skeleton. The compound of Formula 1 may be embodied in at least one of the following Formulas 4 to 7. However, it is not particularly limited thereto.
[화학식 4][Formula 4]
[화학식 5][Formula 5]
[화학식 6][Formula 6]
[화학식 7][Formula 7]
상기 화학식 4 내지 7에서, Ar1 및 Ar2는 각각 상기 화학식 1에서 정의한 바와 같다.In Formulas 4 to 7, Ar 1 and Ar 2 are each as defined in Formula 1 above.
바람직하게는, 상기 화학식 1로 표시되는 화합물은 상기 화학식 6으로 구체화될 수 있다. 이때, 카바졸의 활성 부위(active site)인 3번 위치가 서로 연결된 화합물이 더욱 바람직하고, 이러한 화합물을 유기 전계 발광 소자의 발광층에 사용할 경우에는 카바졸의 3번 위치가 open 상태인 화합물에 비해 재료의 안전성이 향상될 수 있다.Preferably, the compound represented by Formula 1 may be specified as Formula 6. At this time, compounds in which the 3-position, which is the active site of carbazole, are connected to each other are more preferable, and when such compounds are used in the light-emitting layer of an organic electroluminescent device, compared to compounds in which the 3-position of carbazole is open, The safety of materials can be improved.
Ar1은 상기 화학식 2 또는 화학식 3으로 표시되는 치환체이다.Ar 1 is a substituent represented by Formula 2 or Formula 3 above.
보다 구체적으로, 상기 화학식 2 또는 3으로 표시되는 치환체에서, X1 내지 X3는 C(R1)(R2), O, S 및 N(R3)로 이루어진 군에서 선택된다.More specifically, in the substituent represented by Formula 2 or 3, X 1 to X 3 are selected from the group consisting of C(R 1 )(R 2 ), O, S, and N(R 3 ).
R1 내지 R3는 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, 혹은 인접하는 기와 결합하여 축합 고리를 형성할 수 있다.R 1 to R 3 are the same or different from each other, and each independently represents hydrogen, deuterium (D), halogen, cyano group, nitro group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C 6 to C 60 aryl group, heteroaryl group with 5 to 60 nuclear atoms, C 1 to 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 Selected from the group consisting of an aryl boron group of 60 , an arylphosphine group of C 6 ~ C 60 , an arylphosphine oxide group of C 6 ~ C 60 , and an arylamine group of C 6 ~ C 60 , or condensed by combining with an adjacent group A ring can be formed.
바람직하게는, 상기 R1 내지 R3는 서로 동일하거나 상이하며, 각각 독립적으로 C1~C40의 알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택될 수 있다.Preferably, R 1 to R 3 are the same or different from each other, and are each independently an alkyl group of C 1 to C 40 , an aryl group of C 6 to C 60 , a heteroaryl group of 5 to 60 nuclear atoms, and a C 6 It may be selected from the group consisting of ~C 60 arylamine groups.
이러한 화학식 2로 표시되는 치환체는 스파이로 모이어티로서 스파이로(안트라센-플루오렌), 스파이로(플루오렌-크산텐), 스파이로(플루오렌-티오크산텐), 스파이로(아크리딘-플루오렌)일 수 있고, 하기 화학식 8 내지 11 중 적어도 어느 하나로 구체화될 수 있다. 그러나, 이에 특별히 한정되지 않는다.The substituents represented by Formula 2 are spiro moieties, such as spiro (anthracene-fluorene), spiro (fluorene-xanthene), spiro (fluorene-thioxanthene), and spiro (acridine- fluorene) and may be embodied in at least one of the following formulas 8 to 11. However, it is not particularly limited thereto.
[화학식 8][Formula 8]
[화학식 9][Formula 9]
[화학식 10][Formula 10]
[화학식 11][Formula 11]
상기 화학식 8 내지 11에서, * 는 상기 화학식 1과 결합하는 부위를 나타내고, R1 내지 R3는 각각 상기 화학식 1에서 정의한 바와 같다.In Formulas 8 to 11, * represents a site that binds to Formula 1, and R 1 to R 3 are each as defined in Formula 1.
또한, 이러한 화학식 3으로 표시되는 치환체는 디하이드로안트라센, 디벤조다이옥신, 티안트렌, 페나진일 수 있고, 하기 화학식 12 내지 15 중 적어도 어느 하나로 구체화될 수 있다. 그러나, 이에 특별히 한정되지 않는다.In addition, the substituent represented by Formula 3 may be dihydroanthracene, dibenzodioxin, thianthrene, or phenazine, and may be embodied in at least one of the following Formulas 12 to 15. However, it is not particularly limited thereto.
[화학식 12][Formula 12]
[화학식 13][Formula 13]
[화학식 14][Formula 14]
[화학식 15][Formula 15]
상기 화학식 12 내지 15에서, * 는 상기 화학식 1과 결합하는 부위를 나타내고, R1 내지 R3는 각각 상기 화학식 1에서 정의한 바와 같다.In Formulas 12 to 15, * represents a site that binds to Formula 1, and R 1 to R 3 are each as defined in Formula 1.
한편, Ar2는 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 선택되며, 이때 Ar2가 C6~C60의 아릴기 또는 핵원자수 5 내지 60의 헤테로아릴기일 경우, 상기 Ar1과 동일하거나 상이할 수 있다.Meanwhile, Ar 2 is 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, nuclear atom Heterocycloalkyl group with 3 to 40 atoms, C 6 to C 60 aryl group, heteroaryl group with 5 to 60 nuclear atoms, C 1 to C 40 alkyloxy group, C 6 to 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 60 aryl boron group, C 6 ~ C 60 arylphosphine group, C It is selected from the group consisting of an arylphosphine oxide group of 6 to C 60 and an arylamine group of C 6 to C 60 , where Ar 2 is an aryl group of C 6 to C 60 or a heteroaryl group of 5 to 60 nuclear atoms. , may be the same as or different from Ar 1 .
바람직하게는, 상기 Ar2는 C1~C40의 알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택될 수 있다. 더욱 바람직하게는, 상기 Ar2는 C6~C60의 아릴기일 수 있다.Preferably, Ar 2 is selected from the group consisting of a C 1 ~ C 40 alkyl group, a C 6 ~ C 60 aryl group, a heteroaryl group with 5 to 60 nuclear atoms, and a C 6 ~ C 60 arylamine group. You can. More preferably, Ar 2 may be an aryl group of C 6 to C 60 .
상기 Ar2, R1 내지 R3의 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기 및 아릴아민기는 각각 독립적으로 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.Ar 2 , R 1 to R 3 alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and aryl amine group are each independently selected from deuterium (D), halogen, cyano group, nitro group, C 1 to C 40 alkyl group, C 2 to C 40 alkene. Nyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C 6 to C 60 aryl group, heteroaryl group with 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 ~ C 60 aryl boron group, C 6 ~ C 60 arylphosphine group, C 6 ~ C 60 arylphosphine oxide group, and C 6 ~ C 60 one or more substituents selected from the group consisting of arylamine group may be substituted, and in this case, when the substituents are plural, they may be the same or different from each other.
이상에서 설명한 본 발명에 따른 화학식 1로 표시되는 화합물은 하기 예시되는 화합물 1 내지 672 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 Formula 1 according to the present invention described above may be further specified as a compound represented by any one of compounds 1 to 672 exemplified below. However, the compound represented by Formula 1 of the present invention is not limited to those exemplified below.
본 발명에서 “알킬”은 탄소수 1 내지 40의 직쇄 또는 측쇄의 포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이러한 알킬의 예로는 메틸, 에틸, 프로필, 이소부틸, sec-부틸, 펜틸, iso-아밀, 헥실 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, “alkyl” refers to a monovalent substituent derived from a straight-chain or branched-chain saturated hydrocarbon having 1 to 40 carbon atoms. Examples of such alkyl include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, and hexyl.
본 발명에서 “알케닐(alkenyl)”은 탄소-탄소 이중 결합을 1개 이상 가진탄소수 2 내지 40의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이러한 알케닐의 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 one or more carbon-carbon double bonds. Examples of such alkenyl include vinyl, allyl, isopropenyl, 2-butenyl, etc., but are not limited thereto.
본 발명에서“알키닐(alkynyl)”은 탄소-탄소 삼중 결합을 1개 이상 가진탄소수 2 내지 40의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이러한 알키닐의 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 and having one or more carbon-carbon triple bonds. Examples of such alkynyl include ethynyl, 2-propynyl, etc., but are not limited thereto.
본 발명에서 “아릴”은 단독 고리 또는 2 이상의 고리가 조합된 탄소수 6 내지 60의 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.In the present invention, “aryl” refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms, either a single ring or a combination of two or more rings. In addition, a form in which two or more rings are simply attached to each other (pendant) or condensed may also be included. Examples of such aryl include phenyl, naphthyl, phenanthryl, anthryl, etc., but are not limited thereto.
본 발명에서 “헤테로아릴”은 핵원자수 5 내지 60의 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.In the present invention, “heteroaryl” refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. At this time, at least one carbon, preferably 1 to 3 carbons, of the ring is replaced with a heteroatom such as N, O, S or Se. In addition, a form in which two or more rings are simply pendant or condensed with each other may be included, and a condensed form with an aryl group may also be included. Examples of such heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl, phenoxathienyl, indolizinyl, and indolyl ( Polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, and 2-furanyl, N-imidazolyl, 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, etc., but are not limited thereto.
본 발명에서 “아릴옥시”는 RO-로 표시되는 1가의 치환기로, 상기 R은 탄소수 6 내지 60의 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-, where R refers to aryl having 6 to 60 carbon atoms. Examples of such aryloxy include phenyloxy, naphthyloxy, diphenyloxy, etc., but are not limited thereto.
본 발명에서 “알킬옥시”는 R’O-로 표시되는 1가의 치환기로, 상기 R’는 탄소수 1 내지 40의 알킬을 의미한다. 이러한 알킬옥시는 직쇄(linear), 측쇄(branched) 또는 사이클릭(cyclic) 구조를 포함할 수 있다. 이러한 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-, where R’ refers to alkyl having 1 to 40 carbon atoms. These alkyloxy may include linear, branched, or cyclic structures. Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, and pentoxy.
본 발명에서 “아릴아민”은 탄소수 6 내지 60의 아릴로 치환된 아민을 의미한다.In the present invention, “arylamine” refers to an amine substituted with aryl having 6 to 60 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.In the present invention, “cycloalkyl” refers to a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, and adamantine.
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.In the present invention, “heterocycloalkyl” refers to a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, and at least one carbon in the ring, preferably 1 to 3 carbons, is N, O, S Or it is substituted with a hetero atom such as Se. Examples of such heterocycloalkyl include, but are not limited to, morpholine and piperazine.
본 발명에서 “알킬실릴”은 탄소수 1 내지 40의 알킬로 치환된 실릴이고, “아릴실릴”은 탄소수 6 내지 60의 아릴로 치환된 실릴을 의미한다.In the present invention, “alkylsilyl” refers to silyl substituted with alkyl having 1 to 40 carbon atoms, and “arylsilyl” refers to silyl substituted with aryl having 6 to 60 carbon atoms.
본 발명에서 “알킬보론”은 탄소수 1 내지 40의 알킬로 치환된 보론이고, “아릴보론”은 탄소수 6 내지 60의 아릴로 치환된 보론을 의미한다.In the present invention, “alkylboron” refers to boron substituted with alkyl having 1 to 40 carbon atoms, and “arylboron” refers to boron substituted with aryl having 6 to 60 carbon atoms.
본 발명에서 "아릴포스핀"은 탄소수 6 내지 60의 아릴로 치환된 포스핀을 의미하고, "아릴포스핀옥사이드기"는 탄소수 6 내지 60의 아릴로 치환된 포스핀이 O를 포함하는 것을 의미한다.In the present invention, “arylphosphine” refers to phosphine substituted with aryl having 6 to 60 carbon atoms, and “arylphosphine oxide group” refers to phosphine substituted with aryl having 6 to 60 carbon atoms containing O. do.
본 발명에서 “축합 고리”는 축합 지방족 고리, 축합 방향족 고리, 축합 헤테로지방족 고리, 축합 헤테로방향족 고리 또는 이들의 조합된 형태를 의미한다.In the present invention, “condensed ring” means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.
이와 같은 본 발명의 화학식 1로 표시되는 화합물은 하기 실시예의 합성과정을 참고하여 다양하게 합성할 수 있다.The compound represented by Formula 1 of the present invention can be synthesized in various ways by referring to the synthesis process in the examples below.
2. 유기 2. Organic 전계electric field 발광 소자 light emitting element
본 발명은 상기 화학식 1로 표시되는 화합물을 포함하는 유기 전계 발광 소자를 제공한다.The present invention provides an organic electroluminescent device containing the compound represented by Formula 1 above.
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 Formula 1 above. At this time, the above compounds may be used alone, or two or more may be used in combination.
상기 1층 이상의 유기물층은 정공 주입층, 정공 수송층, 발광 보조층, 발광층, 전자 수송층 및 전자 주입층 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 발광층인 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, and among these, at least one organic material layer may include a compound represented by Formula 1. there is. Specifically, it is preferable that the organic material layer containing the compound of Formula 1 is a light-emitting layer.
본 발명의 유기 전계 발광 소자의 발광층은 호스트 재료(바람직하게는, 인광 호스트 재료)를 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 (preferably, a phosphorescent host material). Additionally, the light-emitting layer of the organic electroluminescent device of the present invention may include a compound other than the compound of Formula 1 above as a host.
이러한 본 발명의 유기 전계 발광 소자의 구조는 특별히 한정되지 않으나, 비제한적인 예로 기판, 양극, 정공 주입층, 정공 수송층, 발광 보조층, 발광층, 전자 수송층 및 음극이 순차적으로 적층된 구조일 수 있다. 이때, 상기 정공 주입층, 정공 수송층, 발광 보조층, 발광층, 전자 수송층 및 전자 주입층 중 하나 이상은 상기 화학식 1로 표시되는 화합물을 포함할 수 있고, 바람직하게는 발광층이 상기 화학식 1로 표시되는 화합물을 포함할 수 있다. 여기서, 상기 전자 수송층 위에는 전자 주입층이 추가로 적층될 수 있다. 또한, 본 발명의 유기 전계 발광 소자의 구조는 전극과 유기물층 계면에 절연층 또는 접착층이 삽입된 구조일 수 있다.The structure of the organic electroluminescent device of the present invention is not particularly limited, but as a non-limiting example, it may have a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, an auxiliary light emitting layer, a light emitting layer, an electron transport layer, and a cathode are sequentially stacked. . At this time, one or more of the hole injection layer, hole transport layer, light emitting auxiliary layer, light emitting layer, electron transport layer, and electron injection layer may include a compound represented by Formula 1, and preferably the light emitting layer is represented by Formula 1. It may contain compounds. Here, an electron injection layer may be additionally stacked on the electron transport layer. Additionally, the structure of the organic electroluminescent device of the present invention may be one in which an insulating layer or an adhesive layer is inserted at the interface between the electrode and the organic material layer.
한편, 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.Meanwhile, the organic electroluminescent device of the present invention can be manufactured by forming an organic material layer and an electrode using materials and methods known in the art, except that at least one layer of the organic material layer contains the compound represented by Formula 1. there is.
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 vacuum deposition or solution application. Examples of the solution application method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.
본 발명의 유기 전계 발광 소자 제조시 사용되는 기판은 특별히 한정되지 않으나, 실리콘 웨이퍼, 석영, 유리판, 금속판, 플라스틱 필름 및 시트 등을 사용할 수 있다.The substrate used in manufacturing the organic electroluminescent device of the present invention is not particularly limited, but silicon wafers, quartz, glass plates, metal plates, plastic films and sheets, etc. can be used.
또한, 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.Additionally, the anode material includes metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO:Al or SnO2: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.
또한, 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.Additionally, the cathode material may include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead, or alloys thereof; and multilayer structure materials such as LiF/Al or LiO2/Al, etc., 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.Additionally, the hole injection layer, hole transport layer, electron injection layer, and electron transport layer are not particularly limited, and common materials known in the art can 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 through examples. However, the following examples only illustrate the present invention, and the present invention is not limited by the following examples.
[[ 준비예Preparation example 1] 3CZN21] 3CZN2 의 합성 synthesis of
질소 기류 하에서 3-chloro-9H-carbazole (20.2 g, 100 mmol), 2'-bromo-10-phenyl-10H-spiro[acridine-9,9'-fluorene] (48.7 g, 100 mmol), Pd2(dba)3 (2.75 g, 3.0 mmol), (t-Bu)3P (4.0 g, 20 mmol), sodium tert-butoxide (NaOBu-t) (19.2 g, 200 mmol)을 toluene (PhMe) 1000 ml에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 3CZN2 (49.9 g, 수율 82 %)를 얻었다.Under nitrogen flow, 3-chloro-9H-carbazole (20.2 g, 100 mmol), 2'-bromo-10-phenyl-10H-spiro[acridine-9,9'-fluorene] (48.7 g, 100 mmol), Pd 2 (dba) 3 (2.75 g, 3.0 mmol), (t-Bu) 3P (4.0 g, 20 mmol), sodium tert-butoxide (NaOBu-t) (19.2 g, 200 mmol) in 1000 ml of toluene (PhMe) and stirred at 110°C for 12 hours. After completion of the reaction, the extract was extracted with methylene chloride, MgSO 4 was added and filtered. After removing the solvent in the filtered organic layer, the target compound 3CZN2 (49.9 g, yield 82%) was obtained using column chromatography.
1H-NMR: δ 7.17 (m, 18H), 7.53 (m, 4H), 7.73 (s, 1H), 7.89 (d, 2H), 8.06 (d, 1H), 8.56 (d, 1H) 1 H-NMR: δ 7.17 (m, 18H), 7.53 (m, 4H), 7.73 (s, 1H), 7.89 (d, 2H), 8.06 (d, 1H), 8.56 (d, 1H)
[[ 준비예Preparation example 2] 3CZN32] 3CZN3 의 합성 synthesis of
3'-bromo-10-phenyl-10H-spiro[acridine-9,9'-fluorene] (20.2 g, 100 mmol)을 사용하는 것을 제외하고는 준비예 1과 동일한 과정을 수행하여 3CZN3 (48.6 g, 수율 80 %)을 얻었다.3CZN3 (48.6 g, Yield 80%) was obtained.
1H-NMR: δ 7.16 (m, 19H), 7.54 (m, 3H), 7.72 (d, 1H), 7.94 (m, 3H), 8.57 (d, 1H) 1 H-NMR: δ 7.16 (m, 19H), 7.54 (m, 3H), 7.72 (d, 1H), 7.94 (m, 3H), 8.57 (d, 1H)
[[ 준비예Preparation example 3] 2CZN23] 2CZN2 의 합성 synthesis of
2-chloro-9H-carbazole (20.2 g, 100 mmol)을 사용하는 것을 제외하고는 준비예 1과 동일한 과정을 수행하여 2CZN2 (47.5 g, 수율 78 %)을 얻었다.2CZN2 (47.5 g, yield 78%) was obtained by performing the same process as Preparation Example 1 except for using 2-chloro-9H-carbazole (20.2 g, 100 mmol).
1H-NMR: δ 7.15 (m, 19H), 7.52 (m, 2H), 7.72 (s, 1H), 7.92 (d, 2H), 8.05 (d, 2H), 8.56 (d, 1H) 1 H-NMR: δ 7.15 (m, 19H), 7.52 (m, 2H), 7.72 (s, 1H), 7.92 (d, 2H), 8.05 (d, 2H), 8.56 (d, 1H)
[[ 준비예Preparation example 4] 2CZN34] 2CZN3 의 합성 synthesis of
2-chloro-9H-carbazole (20.2 g, 100 mmol)을 사용하는 것을 제외하고는 준비예 2와 동일한 과정을 수행하여 2CZN3 (45.6 g, 수율 75 %)을 얻었다.2CZN3 (45.6 g, yield 75%) was obtained by performing the same process as Preparation Example 2 except for using 2-chloro-9H-carbazole (20.2 g, 100 mmol).
1H-NMR: δ 7.21 (m, 20H), 7.55 (d, 1H), 7.69 (d, 1H), 7.93 (m, 3H), 8.05 (d, 1H), 8.57 (d, 1H) 1 H-NMR: δ 7.21 (m, 20H), 7.55 (d, 1H), 7.69 (d, 1H), 7.93 (m, 3H), 8.05 (d, 1H), 8.57 (d, 1H)
[[ 준비예Preparation example 5] 1CZN25] 1CZN2 의 합성 synthesis of
1-chloro-9H-carbazole (20.2 g, 100 mmol)을 사용하는 것을 제외하고는 준비예 1과 동일한 과정을 수행하여 1CZN2 (43.8 g, 수율 72 %)을 얻었다.1CZN2 (43.8 g, yield 72%) was obtained by performing the same process as Preparation Example 1 except for using 1-chloro-9H-carbazole (20.2 g, 100 mmol).
1H-NMR: δ 7.22 (m, 19H), 7.53 (m, 2H), 7.71 (s, 1H), 7.92 (d, 2H), 8.06 (d, 2H), 8.56 (d, 1H) 1 H-NMR: δ 7.22 (m, 19H), 7.53 (m, 2H), 7.71 (s, 1H), 7.92 (d, 2H), 8.06 (d, 2H), 8.56 (d, 1H)
[[ 준비예Preparation example 6] 1CZN36] 1CZN3 의 합성 synthesis of
1-chloro-9H-carbazole (20.2 g, 100 mmol)을 사용하는 것을 제외하고는 준비예 2와 동일한 과정을 수행하여 1CZN3 (44.4 g, 수율 73 %)을 얻었다.1CZN3 (44.4 g, yield 73%) was obtained by performing the same process as Preparation Example 2 except for using 1-chloro-9H-carbazole (20.2 g, 100 mmol).
1H-NMR: δ 7.20 (m, 20H), 7.55 (d, 1H), 7.71 (d, 1H), 7.93 (m, 3H), 8.06 (d, 1H), 8.57 (d, 1H) 1 H-NMR: δ 7.20 (m, 20H), 7.55 (d, 1H), 7.71 (d, 1H), 7.93 (m, 3H), 8.06 (d, 1H), 8.57 (d, 1H)
[[ 준비예Preparation example 7] 4CZN27] 4CZN2 의 합성 synthesis of
4-chloro-9H-carbazole (20.2 g, 100 mmol)을 사용하는 것을 제외하고는 준비예 1과 동일한 과정을 수행하여 4CZN2 (48.6 g, 수율 80 %)을 얻었다.4CZN2 (48.6 g, yield 80%) was obtained by performing the same process as Preparation Example 1 except for using 4-chloro-9H-carbazole (20.2 g, 100 mmol).
1H-NMR: δ 7.19 (m, 22H), 7.61 (s, 1H), 7.92 (d, 2H), 8.03 (d, 1H), 8.56 (d, 1H)) 1 H-NMR: δ 7.19 (m, 22H), 7.61 (s, 1H), 7.92 (d, 2H), 8.03 (d, 1H), 8.56 (d, 1H))
[[ 준비예Preparation example 8] 4CZN38] 4CZN3 의 합성 synthesis of
4-chloro-9H-carbazole (20.2 g, 100 mmol)을 사용하는 것을 제외하고는 준비예 2와 동일한 과정을 수행하여 4CZN3 (48.1 g, 수율 79 %)을 얻었다.4CZN3 (48.1 g, yield 79%) was obtained by performing the same process as Preparation Example 2 except for using 4-chloro-9H-carbazole (20.2 g, 100 mmol).
1H-NMR: δ 7.19 (m, 21H), 7.56 (d, 1H), 7.86 (d, 1H), 7.93 (m, 3H), 8.57 (d, 1H) 1 H-NMR: δ 7.19 (m, 21H), 7.56 (d, 1H), 7.86 (d, 1H), 7.93 (m, 3H), 8.57 (d, 1H)
[[ 준비예Preparation example 9] 3CZO29] 3CZO2 의 합성 synthesis of
질소 기류 하에서 3-chloro-9H-carbazole (20.2 g, 100 mmol), 2-bromospiro[fluorene-9,9'-xanthene] (41.2 g, 100 mmol), Pd2(dba)3 (2.75 g, 3.0 mmol), (t-Bu)3P (4.0 g, 20 mmol), sodium tert-butoxide (19.2 g, 200 mmol)을 toluene 1000 ml에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 3CZO2 (48.6 g, 수율 80 %)를 얻었다. Under nitrogen flow, 3-chloro-9H-carbazole (20.2 g, 100 mmol), 2-bromospiro[fluorene-9,9'-xanthene] (41.2 g, 100 mmol), Pd 2 (dba) 3 (2.75 g, 3.0 mmol), (t-Bu) 3 P (4.0 g, 20 mmol), and sodium tert-butoxide (19.2 g, 200 mmol) were added to 1000 ml of toluene and stirred at 110°C for 12 hours. After completion of the reaction, the extract was extracted with methylene chloride, MgSO 4 was added and filtered. After removing the solvent in the filtered organic layer, the target compound 3CZO2 (48.6 g, yield 80%) was obtained using column chromatography.
1H-NMR: δ 7.09 (m, 8H), 7.34 (t, 5H), 7.53 (m, 4H), 7.65 (s, 1H), 7.93 (d, 2H), 8.06 (d, 1H), 8.54 (d, 1H) 1 H-NMR: δ 7.09 (m, 8H), 7.34 (t, 5H), 7.53 (m, 4H), 7.65 (s, 1H), 7.93 (d, 2H), 8.06 (d, 1H), 8.54 ( d, 1H)
[[ 준비예Preparation example 10] 3CZO310] 3CZO3 의 합성 synthesis of
3-bromospiro[fluorene-9,9'-xanthene] (41.2 g, 100 mmol)을 사용하는 것을 제외하고는 준비예 9과 동일한 과정을 수행하여 3CZO3 (48.1 g, 수율 79 %)을 얻었다.3CZO3 (48.1 g, yield 79%) was obtained by performing the same process as Preparation Example 9 except for using 3-bromospiro[fluorene-9,9'-xanthene] (41.2 g, 100 mmol).
1H-NMR: δ 7.07 (m, 8H), 7.35 (m, 6H), 7.53 (m, 3H), 7.64 (d, 1H), 7.93 (m, 3H), 8.54 (d, 1H) 1 H-NMR: δ 7.07 (m, 8H), 7.35 (m, 6H), 7.53 (m, 3H), 7.64 (d, 1H), 7.93 (m, 3H), 8.54 (d, 1H)
[[ 준비예Preparation example 11] 2CZO211] 2CZO2 의 합성 synthesis of
2-chloro-9H-carbazole (20.2 g, 100 mmol)을 사용하는 것을 제외하고는 준비예 9과 동일한 과정을 수행하여 2CZO2 (46.8 g, 수율 77 %)을 얻었다.2CZO2 (46.8 g, yield 77%) was obtained by performing the same process as Preparation Example 9 except for using 2-chloro-9H-carbazole (20.2 g, 100 mmol).
1H-NMR: δ 7.03 (m, 3H), 7.15 (m, 5H), 7.35 (m, 6H), 7.55 (d, 2H), 7.65 (s, 1H), 7.92 (d, 2H), 8.05 (d, 2H), 8.54 (d, 1H) 1 H-NMR: δ 7.03 (m, 3H), 7.15 (m, 5H), 7.35 (m, 6H), 7.55 (d, 2H), 7.65 (s, 1H), 7.92 (d, 2H), 8.05 ( d, 2H), 8.54 (d, 1H)
[[ 준비예Preparation example 12] 2CZO312] 2CZO3 의 합성 synthesis of
2-chloro-9H-carbazole (20.2 g, 100 mmol)을 사용하는 것을 제외하고는 준비예 10와 동일한 과정을 수행하여 2CZO3 (49.3 g, 수율 81 %)을 얻었다.2CZO3 (49.3 g, yield 81%) was obtained by performing the same process as Preparation Example 10 except for using 2-chloro-9H-carbazole (20.2 g, 100 mmol).
1H-NMR: δ 7.02 (m, 3H), 7.15 (m, 5H), 7.36 (m, 7H), 7.54 (d, 1H), 7.67 (d, 1H), 7.93 (m, 3H), 8.04 (d, 1H), 8.56 (d, 1H) 1 H-NMR: δ 7.02 (m, 3H), 7.15 (m, 5H), 7.36 (m, 7H), 7.54 (d, 1H), 7.67 (d, 1H), 7.93 (m, 3H), 8.04 ( d, 1H), 8.56 (d, 1H)
[[ 준비예Preparation example 13] 1CZO213] 1CZO2 의 합성 synthesis of
1-chloro-9H-carbazole (20.2 g, 100 mmol)을 사용하는 것을 제외하고는 준비예 9과 동일한 과정을 수행하여 1CZO2 (41.9 g, 수율 69 %)을 얻었다.1CZO2 (41.9 g, yield 69%) was obtained by performing the same process as Preparation Example 9 except for using 1-chloro-9H-carbazole (20.2 g, 100 mmol).
1H-NMR: δ 7.18 (m, 14H), 7.52 (d, 2H), 7.63 (s, 1H), 7.93 (d, 2H), 8.05 (d, 2H), 8.56 (d, 1H) 1 H-NMR: δ 7.18 (m, 14H), 7.52 (d, 2H), 7.63 (s, 1H), 7.93 (d, 2H), 8.05 (d, 2H), 8.56 (d, 1H)
[[ 준비예Preparation example 14] 1CZO314] 1CZO3 의 합성 synthesis of
1-chloro-9H-carbazole (20.2 g, 100 mmol)을 사용하는 것을 제외하고는 준비예 10와 동일한 과정을 수행하여 1CZO3 (42.6 g, 수율 70 %)을 얻었다.1CZO3 (42.6 g, yield 70%) was obtained by performing the same process as Preparation Example 10 except for using 1-chloro-9H-carbazole (20.2 g, 100 mmol).
1H-NMR: δ 7.21 (m, 15H), 7.54 (d, 1H), 7.67 (d, 1H), 7.94 (m, 3H), 8.05 (d, 1H), 8.54 (d, 1H) 1 H-NMR: δ 7.21 (m, 15H), 7.54 (d, 1H), 7.67 (d, 1H), 7.94 (m, 3H), 8.05 (d, 1H), 8.54 (d, 1H)
[[ 준비예Preparation example 15] 4CZO215] 4CZO2 의 합성 synthesis of
4-chloro-9H-carbazole (20.2 g, 100 mmol)을 사용하는 것을 제외하고는 준비예 9과 동일한 과정을 수행하여 4CZO2 (45.6 g, 수율 75 %)을 얻었다.The same process as Preparation Example 9 was performed except for using 4-chloro-9H-carbazole (20.2 g, 100 mmol) to obtain 4CZO2 (45.6 g, yield 75%).
1H-NMR: δ 7.02 (m, 3H), 7.15 (m, 5H), 7.34 (m, 9H), 7.66 (s, 1H), 7.92 (d, 2H), 8.03 (d, 1H), 8.54 (d, 1H) 1 H-NMR: δ 7.02 (m, 3H), 7.15 (m, 5H), 7.34 (m, 9H), 7.66 (s, 1H), 7.92 (d, 2H), 8.03 (d, 1H), 8.54 ( d, 1H)
[[ 준비예Preparation example 16] 4CZO316] 4CZO3 의 합성 synthesis of
4-chloro-9H-carbazole (20.2 g, 100 mmol)을 사용하는 것을 제외하고는 준비예 10와 동일한 과정을 수행하여 4CZO3 (44.4 g, 수율 73 %)을 얻었다.The same process as Preparation Example 10 was performed except for using 4-chloro-9H-carbazole (20.2 g, 100 mmol) to obtain 4CZO3 (44.4 g, yield 73%).
1H-NMR: δ 7.02 (m, 3H), 7.16 (m, 5H), 7.36 (m, 8H), 7.54 (d, 1H), 7.68 (d, 1H), 7.94 (m, 3H), 8.56 (d, 1H) 1 H-NMR: δ 7.02 (m, 3H), 7.16 (m, 5H), 7.36 (m, 8H), 7.54 (d, 1H), 7.68 (d, 1H), 7.94 (m, 3H), 8.56 ( d, 1H)
[[ 준비예Preparation example 17] 3CZS217] 3CZS2 의 합성 synthesis of
질소 기류 하에서 3-chloro-9H-carbazole (20.2 g, 100 mmol), 2-bromospiro[fluorene-9,9'-thioxanthene] (42.8 g, 100 mmol), Pd2(dba)3 (2.75 g, 3.0 mmol), (t-Bu)3P (4.0 g, 20 mmol), sodium tert-butoxide (19.2 g, 200 mmol)을 toluene 1000 ml에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 3CZS2 (48.1 g, 수율 79 %)를 얻었다. Under nitrogen flow, 3-chloro-9H-carbazole (20.2 g, 100 mmol), 2-bromospiro[fluorene-9,9'-thioxanthene] (42.8 g, 100 mmol), Pd 2 (dba) 3 (2.75 g, 3.0 mmol), (t-Bu) 3 P (4.0 g, 20 mmol), and sodium tert-butoxide (19.2 g, 200 mmol) were added to 1000 ml of toluene and stirred at 110°C for 12 hours. After completion of the reaction, it was extracted with methylene chloride, MgSO 4 was added, and filtered. After removing the solvent in the filtered organic layer, the target compound 3CZS2 (48.1 g, yield 79%) was obtained using column chromatography.
1H-NMR: δ 7.21 (m, 12H), 7.52 (d, 2H), 7.67 (m, 3H), 7.92 (d, 2H), 8.06 (d, 2H), 8.57 (d, 1H) 1 H-NMR: δ 7.21 (m, 12H), 7.52 (d, 2H), 7.67 (m, 3H), 7.92 (d, 2H), 8.06 (d, 2H), 8.57 (d, 1H)
[[ 준비예Preparation example 18] 3CZS318] 3CZS3 의 합성 synthesis of
3-bromospiro[fluorene-9,9'-thioxanthene] (42.8 g, 100 mmol)을 사용하는 것을 제외하고는 준비예 17과 동일한 과정을 수행하여 3CZS3 (49.3 g, 수율 81 %)을 얻었다.3CZS3 (49.3 g, yield 81%) was obtained by performing the same process as Preparation Example 17 except for using 3-bromospiro[fluorene-9,9'-thioxanthene] (42.8 g, 100 mmol).
1H-NMR: δ 7.11 (m, 6H), 7.35 (t, 6H), 7.53 (m, 3H), 7.68 (d, 3H), 7.95 (m, 3H), 8.54 (d, 1H) 1 H-NMR: δ 7.11 (m, 6H), 7.35 (t, 6H), 7.53 (m, 3H), 7.68 (d, 3H), 7.95 (m, 3H), 8.54 (d, 1H)
[[ 준비예Preparation example 19] 2CZS219] 2CZS2 의 합성 synthesis of
2-chloro-9H-carbazole (20.2 g, 100 mmol)을 사용하는 것을 제외하고는 준비예 17과 동일한 과정을 수행하여 2CZS2 (45.0 g, 수율 74 %)을 얻었다.2CZS2 (45.0 g, yield 74%) was obtained by performing the same process as Preparation Example 17 except for using 2-chloro-9H-carbazole (20.2 g, 100 mmol).
1H-NMR: δ 7.02 (m, 5H), 7.18 (t, 1H), 7.37 (m, 6H), 7.53 (d, 2H), 7.68 (m, 3H), 7.98 (d, 2H), 8.06 (d, 2H), 8.54 (d, 1H) 1 H-NMR: δ 7.02 (m, 5H), 7.18 (t, 1H), 7.37 (m, 6H), 7.53 (d, 2H), 7.68 (m, 3H), 7.98 (d, 2H), 8.06 ( d, 2H), 8.54 (d, 1H)
[[ 준비예Preparation example 20] 2CZS320] 2CZS3 의 합성 synthesis of
2-chloro-9H-carbazole (20.2 g, 100 mmol)을 사용하는 것을 제외하고는 준비예 18와 동일한 과정을 수행하여 2CZS3 (46.2 g, 수율 76 %)을 얻었다.2CZS3 (46.2 g, yield 76%) was obtained by performing the same process as Preparation Example 18 except for using 2-chloro-9H-carbazole (20.2 g, 100 mmol).
1H-NMR: δ 7.02 (m, 5H), 7.15 (t, 1H), 7.36 (m, 7H), 7.56 (d, 1H), 7.68 (d, 3H), 7.93 (m, 3H), 8.04 (d, 1H), 8.54 (d, 1H) 1 H-NMR: δ 7.02 (m, 5H), 7.15 (t, 1H), 7.36 (m, 7H), 7.56 (d, 1H), 7.68 (d, 3H), 7.93 (m, 3H), 8.04 ( d, 1H), 8.54 (d, 1H)
[[ 준비예Preparation example 21] 1CZS221] 1CZS2 의 합성 synthesis of
1-chloro-9H-carbazole (20.2 g, 100 mmol)을 사용하는 것을 제외하고는 준비예 17과 동일한 과정을 수행하여 1CZS2 (41.4 g, 수율 68 %)을 얻었다.1CZS2 (41.4 g, yield 68%) was obtained by performing the same process as Preparation Example 17 except for using 1-chloro-9H-carbazole (20.2 g, 100 mmol).
1H-NMR: δ 7.24 (m, 12H), 7.51 (d, 2H), 7.68 (m, 3H), 7.92 (d, 2H), 8.05 (d, 2H), 8.57 (d, 1H) 1 H-NMR: δ 7.24 (m, 12H), 7.51 (d, 2H), 7.68 (m, 3H), 7.92 (d, 2H), 8.05 (d, 2H), 8.57 (d, 1H)
[[ 준비예Preparation example 22] 1CZS322] 1CZS3 의 합성 synthesis of
1-chloro-9H-carbazole (20.2 g, 100 mmol)을 사용하는 것을 제외하고는 준비예 18와 동일한 과정을 수행하여 1CZS3 (43.2 g, 수율 71 %)을 얻었다.1CZS3 (43.2 g, yield 71%) was obtained by performing the same process as Preparation Example 18 except for using 1-chloro-9H-carbazole (20.2 g, 100 mmol).
1H-NMR: δ 7.22 (m, 13H), 7.56 (d, 1H), 7.68 (d, 3H), 7.93 (m, 3H), 8.06 (d, 1H), 8.56 (d, 1H) 1 H-NMR: δ 7.22 (m, 13H), 7.56 (d, 1H), 7.68 (d, 3H), 7.93 (m, 3H), 8.06 (d, 1H), 8.56 (d, 1H)
[[ 준비예Preparation example 23] 4CZS223] 4CZS2 의 합성 synthesis of
4-chloro-9H-carbazole (20.2 g, 100 mmol)을 사용하는 것을 제외하고는 준비예 17과 동일한 과정을 수행하여 4CZS2 (45.0 g, 수율 74 %)을 얻었다.4CZS2 (45.0 g, yield 74%) was obtained by performing the same process as Preparation Example 17 except for using 4-chloro-9H-carbazole (20.2 g, 100 mmol).
1H-NMR: δ 7.02 (m, 5H), 7.15 (t, 1H), 7.35 (m, 9H), 7.67 (m, 3H), 7.92 (d, 2H), 8.03 (d, 1H), 8.56 (d, 1H) 1 H-NMR: δ 7.02 (m, 5H), 7.15 (t, 1H), 7.35 (m, 9H), 7.67 (m, 3H), 7.92 (d, 2H), 8.03 (d, 1H), 8.56 ( d, 1H)
[[ 준비예Preparation example 24] 4CZS324] 4CZS3 의 합성 synthesis of
4-chloro-9H-carbazole (20.2 g, 100 mmol)을 사용하는 것을 제외하고는 준비예 18와 동일한 과정을 수행하여 4CZS3 (43.8 g, 수율 72 %)을 얻었다.The same process as Preparation Example 18 was performed except for using 4-chloro-9H-carbazole (20.2 g, 100 mmol) to obtain 4CZS3 (43.8 g, yield 72%).
1H-NMR: δ 7.02 (m, 5H), 7.14 (t, 1H), 7.34 (m, 8H), 7.64 (d, 1H), 7.68 (d, 3H), 7.93 (m, 3H), 8.56 (d, 1H) 1 H-NMR: δ 7.02 (m, 5H), 7.14 (t, 1H), 7.34 (m, 8H), 7.64 (d, 1H), 7.68 (d, 3H), 7.93 (m, 3H), 8.56 ( d, 1H)
[[ 준비예Preparation example 25] 3CZF225] 3CZF2 의 합성 synthesis of
질소 기류 하에서 3-chloro-9H-carbazole (20.2 g, 100 mmol), 2'-bromo-10,10-dimethyl-10H-spiro[anthracene-9,9'-fluorene] (43.8 g, 100 mmol), Pd2(dba)3 (2.75 g, 3.0 mmol), (t-Bu)3P (4.0 g, 20 mmol), sodium tert-butoxide (19.2 g, 200 mmol)을 toluene 1000 ml에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 3CZF2 (50.5 g, 수율 83 %)를 얻었다. 3-chloro-9H-carbazole (20.2 g, 100 mmol), 2'-bromo-10,10-dimethyl-10H-spiro[anthracene-9,9'-fluorene] (43.8 g, 100 mmol), under nitrogen flow. Pd 2 (dba) 3 (2.75 g, 3.0 mmol), (t-Bu) 3 P (4.0 g, 20 mmol), and sodium tert-butoxide (19.2 g, 200 mmol) were added to 1000 ml of toluene and incubated at 110°C for 12 days. Stirred for an hour. After completion of the reaction, extraction was performed with methylene chloride, MgSO 4 was added, and the mixture was filtered. After removing the solvent in the filtered organic layer, the target compound 3CZF2 (50.5 g, yield 83%) was obtained using column chromatography.
1H-NMR: δ 1.68 (s, 6H), 7.34 (m, 18H), 7.88 (d, 2H), 8.05 (d, 1H), 8.56 (d, 1H) 1 H-NMR: δ 1.68 (s, 6H), 7.34 (m, 18H), 7.88 (d, 2H), 8.05 (d, 1H), 8.56 (d, 1H)
[[ 준비예Preparation example 26] 3CZF326] 3CZF3 의 합성 synthesis of
3'-bromo-10,10-dimethyl-10H-spiro[anthracene-9,9'-fluorene] (43.8 g, 100 mmol)을 사용하는 것을 제외하고는 준비예 25과 동일한 과정을 수행하여 3CZF3 (48.7 g, 수율 80 %)을 얻었다.3CZF3 (48.7 g, yield 80%) was obtained.
1H-NMR: δ 1.68 (s, 6H), 7.36 (m, 18H), 7.92 (m, 3H), 8.56 (d, 1H) 1 H-NMR: δ 1.68 (s, 6H), 7.36 (m, 18H), 7.92 (m, 3H), 8.56 (d, 1H)
[[ 준비예Preparation example 27] 2CZF227] 2CZF2 의 합성 synthesis of
2-chloro-9H-carbazole (20.2 g, 100 mmol)을 사용하는 것을 제외하고는 준비예 25과 동일한 과정을 수행하여 2CZF2 (47.5 g, 수율 78 %)을 얻었다.2CZF2 (47.5 g, yield 78%) was obtained by performing the same process as Preparation Example 25 except for using 2-chloro-9H-carbazole (20.2 g, 100 mmol).
1H-NMR: δ 1.68 (s, 6H), 7.02 (d, 1H), 7.28 (m, 15H), 7.58 (s, 1H), 7.92 (d, 2H), 8.05 (d, 1H), 8.56 (d, 1H) 1 H-NMR: δ 1.68 (s, 6H), 7.02 (d, 1H), 7.28 (m, 15H), 7.58 (s, 1H), 7.92 (d, 2H), 8.05 (d, 1H), 8.56 ( d, 1H)
[[ 준비예Preparation example 28] 2CZF328] 2CZF3 의 합성 synthesis of
2-chloro-9H-carbazole (20.2 g, 100 mmol)을 사용하는 것을 제외하고는 준비예 26와 동일한 과정을 수행하여 2CZF3 (43.8 g, 수율 72 %)을 얻었다.2CZF3 (43.8 g, yield 72%) was obtained by performing the same process as Preparation Example 26 except for using 2-chloro-9H-carbazole (20.2 g, 100 mmol).
1H-NMR: δ 1.68 (s, 6H), 7.02 (d, 1H), 7.31 (m, 15H), 7.58 (d, 1H), 7.92 (m, 3H), 8.05 (d, 1H), 8.56 (d, 1H) 1 H-NMR: δ 1.68 (s, 6H), 7.02 (d, 1H), 7.31 (m, 15H), 7.58 (d, 1H), 7.92 (m, 3H), 8.05 (d, 1H), 8.56 ( d, 1H)
[[ 준비예Preparation example 29] 1CZF229] 1CZF2 의 합성 synthesis of
1-chloro-9H-carbazole (20.2 g, 100 mmol)을 사용하는 것을 제외하고는 준비예 25과 동일한 과정을 수행하여 1CZF2 (42.6 g, 수율 70 %)을 얻었다.1CZF2 (42.6 g, yield 70%) was obtained by performing the same process as Preparation Example 25 except for using 1-chloro-9H-carbazole (20.2 g, 100 mmol).
1H-NMR: δ 1.68 (s, 6H), 7.30 (m, 16H), 7.58 (s, 1H), 7.92 (d, 2H), 8.06 (d, 2H), 8.54 (d, 1H) 1 H-NMR: δ 1.68 (s, 6H), 7.30 (m, 16H), 7.58 (s, 1H), 7.92 (d, 2H), 8.06 (d, 2H), 8.54 (d, 1H)
[[ 준비예Preparation example 30] 1CZF330] 1CZF3 의 합성 synthesis of
1-chloro-9H-carbazole (20.2 g, 100 mmol)을 사용하는 것을 제외하고는 준비예 26와 동일한 과정을 수행하여 1CZF3 (44.4 g, 수율 73 %)을 얻었다.1CZF3 (44.4 g, yield 73%) was obtained by performing the same process as Preparation Example 26 except for using 1-chloro-9H-carbazole (20.2 g, 100 mmol).
1H-NMR: δ 1.68 (s, 6H), 7.26 (m, 16H), 7.56 (d, 1H), 7.92 (m, 3H), 8.06 (d, 1H), 8.56 (d, 1H) 1 H-NMR: δ 1.68 (s, 6H), 7.26 (m, 16H), 7.56 (d, 1H), 7.92 (m, 3H), 8.06 (d, 1H), 8.56 (d, 1H)
[[ 준비예Preparation example 31] 4CZF231] 4CZF2 의 합성 synthesis of
4-chloro-9H-carbazole (20.2 g, 100 mmol)을 사용하는 것을 제외하고는 준비예 25과 동일한 과정을 수행하여 4CZF2 (49.3 g, 수율 81 %)을 얻었다.4CZF2 (49.3 g, yield 81%) was obtained by performing the same process as Preparation Example 25 except for using 4-chloro-9H-carbazole (20.2 g, 100 mmol).
1H-NMR: δ 1.68 (s, 6H), 7.02 (d, 1H), 7.28 (m, 16H), 7.57 (s, 1H), 7.93 (d, 2H), 8.02 (d, 1H), 8.56 (d, 1H) 1 H-NMR: δ 1.68 (s, 6H), 7.02 (d, 1H), 7.28 (m, 16H), 7.57 (s, 1H), 7.93 (d, 2H), 8.02 (d, 1H), 8.56 ( d, 1H)
[[ 준비예Preparation example 32] 4CZF332] 4CZF3 의 합성 synthesis of
4-chloro-9H-carbazole (20.2 g, 100 mmol)을 사용하는 것을 제외하고는 준비예 26와 동일한 과정을 수행하여 4CZF3 (48.7 g, 수율 80 %)을 얻었다.The same process as Preparation Example 26 was performed except for using 4-chloro-9H-carbazole (20.2 g, 100 mmol) to obtain 4CZF3 (48.7 g, yield 80%).
1H-NMR: δ 1.68 (s, 6H), 7.02 (d, 1H), 7.27 (m, 16H), 7.58 (d, 1H), 7.92 (m, 3H), 8.54 (d, 1H) 1 H-NMR: δ 1.68 (s, 6H), 7.02 (d, 1H), 7.27 (m, 16H), 7.58 (d, 1H), 7.92 (m, 3H), 8.54 (d, 1H)
[[ 준비예Preparation example 33] 3CZOO233] 3CZOO2 의 합성 synthesis of
질소 기류 하에서 3-chloro-9H-carbazole (20.2 g, 100 mmol), 2-bromodibenzo[b,e][1,4]dioxine (26.35 g, 100 mmol), Pd2(dba)3 (2.75 g, 3.0 mmol), (t-Bu)3P (4.0 g, 20 mmol), sodium tert-butoxide (19.2 g, 200 mmol)을 toluene 1000 ml에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 3CZOO2 (49.9 g, 수율 82 %)를 얻었다. 3-chloro-9H-carbazole (20.2 g, 100 mmol), 2-bromodibenzo[b,e][1,4]dioxine (26.35 g, 100 mmol), Pd 2 (dba) 3 (2.75 g, 3.0 mmol), (t-Bu) 3 P (4.0 g, 20 mmol), and sodium tert-butoxide (19.2 g, 200 mmol) were added to 1000 ml of toluene and stirred at 110°C for 12 hours. After completion of the reaction, it was extracted with methylene chloride, MgSO 4 was added, and filtered. After removing the solvent in the filtered organic layer, the target compound 3CZOO2 (49.9 g, yield 82%) was obtained using column chromatography.
1H-NMR: δ 6.81 (d, 2H), 6.96 (m, 3H), 7.13 (m, 3H), 7.39 (m, 2H), 7.54 (m, 2H), 7.96 (d, 1H), 8.56 (d, 1H) 1 H-NMR: δ 6.81 (d, 2H), 6.96 (m, 3H), 7.13 (m, 3H), 7.39 (m, 2H), 7.54 (m, 2H), 7.96 (d, 1H), 8.56 ( d, 1H)
[[ 준비예Preparation example 34] 3CZOO134] 3CZOO1 의 합성 synthesis of
1-bromodibenzo[b,e][1,4]dioxine (26.35 g, 100 mmol)을 사용하는 것을 제외하고는 준비예 33과 동일한 과정을 수행하여 3CZOO1 (48.1 g, 수율 79 %)을 얻었다.3CZOO1 (48.1 g, yield 79%) was obtained by performing the same process as Preparation Example 33 except for using 1-bromodibenzo[b,e][1,4]dioxine (26.35 g, 100 mmol).
1H-NMR: δ 6.81 (d, 3H), 6.92 (t, 2H), 7.16 (m, 3H), 7.38 (m, 2H), 7.54 (m, 2H), 7.95 (d, 1H), 8.56 (d, 1H) 1 H-NMR: δ 6.81 (d, 3H), 6.92 (t, 2H), 7.16 (m, 3H), 7.38 (m, 2H), 7.54 (m, 2H), 7.95 (d, 1H), 8.56 ( d, 1H)
[[ 준비예Preparation example 35] 2CZOO235] 2CZOO2 의 합성 synthesis of
2-chloro-9H-carbazole (20.2 g, 100 mmol)을 사용하는 것을 제외하고는 준비예 33과 동일한 과정을 수행하여 2CZOO2 (46.8 g, 수율 77 %)을 얻었다.2CZOO2 (46.8 g, yield 77%) was obtained by performing the same process as Preparation Example 33 except for using 2-chloro-9H-carbazole (20.2 g, 100 mmol).
1H-NMR: δ 6.81 (d, 2H), 7.08 (m, 6H), 7.38 (m, 3H), 7.92 (d, 1H), 8.05 (d, 1H), 8.56 (d, 1H) 1 H-NMR: δ 6.81 (d, 2H), 7.08 (m, 6H), 7.38 (m, 3H), 7.92 (d, 1H), 8.05 (d, 1H), 8.56 (d, 1H)
[[ 준비예Preparation example 36] 2CZOO136] 2CZOO1 의 합성 synthesis of
2-chloro-9H-carbazole (20.2 g, 100 mmol)을 사용하는 것을 제외하고는 준비예 34와 동일한 과정을 수행하여 2CZOO1 (48.1 g, 수율 79 %)을 얻었다.2CZOO1 (48.1 g, yield 79%) was obtained by performing the same process as Preparation Example 34 except for using 2-chloro-9H-carbazole (20.2 g, 100 mmol).
1H-NMR: δ 6.81 (d, 3H), 6.96 (m, 3H), 7.16 (t, 2H), 7.37 (m, 3H), 7.93 (d, 1H), 8.05 (d, 1H), 8.56 (d, 1H) 1 H-NMR: δ 6.81 (d, 3H), 6.96 (m, 3H), 7.16 (t, 2H), 7.37 (m, 3H), 7.93 (d, 1H), 8.05 (d, 1H), 8.56 ( d, 1H)
[[ 준비예Preparation example 37] 1CZOO237] 1CZOO2 의 합성 synthesis of
1-chloro-9H-carbazole (20.2 g, 100 mmol)을 사용하는 것을 제외하고는 준비예 33과 동일한 과정을 수행하여 1CZOO2 (43.8 g, 수율 72 %)을 얻었다.1CZOO2 (43.8 g, yield 72%) was obtained by performing the same process as Preparation Example 33 except for using 1-chloro-9H-carbazole (20.2 g, 100 mmol).
1H-NMR: δ 6.81 (d, 2H), 6.97 (m, 3H), 7.17 (m, 4H), 7.38 (m, 2H), 7.93 (d, 1H), 8.08 (d, 1H), 8.56 (d, 1H) 1 H-NMR: δ 6.81 (d, 2H), 6.97 (m, 3H), 7.17 (m, 4H), 7.38 (m, 2H), 7.93 (d, 1H), 8.08 (d, 1H), 8.56 ( d, 1H)
[[ 준비예Preparation example 38] 1CZOO138] 1CZOO1 의 합성 synthesis of
1-chloro-9H-carbazole (20.2 g, 100 mmol)을 사용하는 것을 제외하고는 준비예 34와 동일한 과정을 수행하여 1CZOO1 (42.6 g, 수율 70 %)을 얻었다.1CZOO1 (42.6 g, yield 70%) was obtained by performing the same process as Preparation Example 34 except for using 1-chloro-9H-carbazole (20.2 g, 100 mmol).
1H-NMR: δ 6.81 (d, 3H), 6.92 (t, 2H), 7.17 (m, 4H), 7.37 (m, 2H), 7.92 (d, 1H), 8.06 (d, 1H), 8.56 (d, 1H) 1 H-NMR: δ 6.81 (d, 3H), 6.92 (t, 2H), 7.17 (m, 4H), 7.37 (m, 2H), 7.92 (d, 1H), 8.06 (d, 1H), 8.56 ( d, 1H)
[[ 준비예Preparation example 39] 4CZOO239] 4CZOO2 의 합성 synthesis of
4-chloro-9H-carbazole (20.2 g, 100 mmol)을 사용하는 것을 제외하고는 준비예 33과 동일한 과정을 수행하여 4CZOO2 (49.3 g, 수율 81 %)을 얻었다.The same process as Preparation Example 33 was performed except for using 4-chloro-9H-carbazole (20.2 g, 100 mmol) to obtain 4CZOO2 (49.3 g, yield 81%).
1H-NMR: δ 6.81 (d, 2H), 7.08 (m, 6H), 7.37 (m, 4H), 7.92 (d, 1H), 8.56 (d, 1H) 1 H-NMR: δ 6.81 (d, 2H), 7.08 (m, 6H), 7.37 (m, 4H), 7.92 (d, 1H), 8.56 (d, 1H)
[[ 준비예Preparation example 40] 4CZOO140] 4CZOO1 의 합성 synthesis of
4-chloro-9H-carbazole (20.2 g, 100 mmol)을 사용하는 것을 제외하고는 준비예 34와 동일한 과정을 수행하여 4CZOO1 (48.7 g, 수율 80 %)을 얻었다.4CZOO1 (48.7 g, yield 80%) was obtained by performing the same process as Preparation Example 34 except for using 4-chloro-9H-carbazole (20.2 g, 100 mmol).
1H-NMR: δ 6.81 (d, 3H), 6.96 (m, 3H), 7.16 (t, 2H), 7.38 (m, 4H), 7.92 (d, 1H), 8.56 (d, 1H) 1 H-NMR: δ 6.81 (d, 3H), 6.96 (m, 3H), 7.16 (t, 2H), 7.38 (m, 4H), 7.92 (d, 1H), 8.56 (d, 1H)
[[ 합성예Synthesis example 1] 화합물1] Compound 1 의1 of 합성 synthesis
질소 기류 하에서 3CZF3 (11.5 g, 20.6 mmol), (9,9-dimethyl-10-phenyl-9,10-dihydroacridin-2-yl)boronic acid (5.9 g, 20.6 mmol), Pd(PPh3)4 (1.2 g, 5 mol%), NaOH (2.5 g, 61.8 mmol)을 400 ml / 100 ml의 THF/H2O를 넣고 80에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 1 (11.8 g, 수율 75 %)을 획득하였다. Under nitrogen flow, 3CZF3 (11.5 g, 20.6 mmol), (9,9-dimethyl-10-phenyl-9,10-dihydroacridin-2-yl)boronic acid (5.9 g, 20.6 mmol), Pd(PPh 3 ) 4 (1.2 g, 5 mol%) and NaOH (2.5 g, 61.8 mmol) were added to 400 ml/100 ml of THF/H 2 O and stirred at 80° C. for 12 hours. After completion of the reaction, the extract was extracted with methylene chloride, MgSO 4 was added and filtered. After removing the solvent in the filtered organic layer, the target compound 1 (11.8 g, yield 75%) was obtained using column chromatography.
Mass : [(M+H)+] : 765Mass : [(M+H) + ] : 765
[[ 합성예Synthesis example 2] 화합물2] Compound 2 의2 of 합성 synthesis
(9-([1,1'-biphenyl]-3-yl)-9H-carbazol-3-yl)boronic acid (7.48 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 2 (12.6 g, 수율 73 %)을 얻었다.The same process as Synthesis Example 1 was performed except for using (9-([1,1'-biphenyl]-3-yl)-9H-carbazol-3-yl)boronic acid (7.48 g, 20.6 mmol) Compound 2 (12.6 g, yield 73%) was obtained.
Mass : [(M+H)+] : 842Mass : [(M+H) + ] : 842
[[ 합성예Synthesis example 3] 화합물3] Compound 5 의5 of 합성 synthesis
(9-(naphthalen-1-yl)-9H-carbazol-3-yl)boronic acid (6.95 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 5 (12.7 g, 수율 76 %)을 얻었다.Compound 5 (12.7 g, Yield 76%) was obtained.
Mass : [(M+H)+] : 816Mass : [(M+H) + ] : 816
[[ 합성예Synthesis example 4] 화합물4] Compound 8 의8 of 합성 synthesis
3CZF2 (11.5 g, 20.6 mmol)와 (9-(triphenylen-2-yl)-9H-carbazol-3-yl)boronic acid (9.01 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 8 (13.6 g, 수율 72 %)을 얻었다.Same process as Synthesis Example 1 except for using 3CZF2 (11.5 g, 20.6 mmol) and (9-(triphenylen-2-yl)-9H-carbazol-3-yl)boronic acid (9.01 g, 20.6 mmol) Compound 8 (13.6 g, yield 72%) was obtained.
Mass : [(M+H)+] : 916Mass : [(M+H) + ] : 916
[[ 합성예Synthesis example 5] 화합물5] Compound 9 의9 of 합성 synthesis
3CZF2 (11.5 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 9 (11.0 g, 수율 70 %)을 얻었다.Compound 9 (11.0 g, yield 70%) was obtained by performing the same procedure as Synthesis Example 1 except for using 3CZF2 (11.5 g, 20.6 mmol).
Mass : [(M+H)+] : 765Mass : [(M+H) + ] : 765
[[ 합성예Synthesis example 6] 화합물6] Compound 11 의11 of 합성 synthesis
3CZF2 (11.5 g, 20.6 mmol)와 (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-3-yl)boronic acid (7.48 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 11 (11.9 g, 수율 69 %)을 얻었다.Except using 3CZF2 (11.5 g, 20.6 mmol) and (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-3-yl)boronic acid (7.48 g, 20.6 mmol) performed the same process as Synthesis Example 1 to obtain compound 11 (11.9 g, yield 69%).
Mass : [(M+H)+] : 842Mass : [(M+H) + ] : 842
[[ 합성예Synthesis example 7] 화합물7] Compound 13 의13 of 합성 synthesis
3CZO2 (10.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 13 (11.7 g, 수율 77 %)을 얻었다.Compound 13 (11.7 g, yield 77%) was obtained by performing the same procedure as Synthesis Example 1 except for using 3CZO2 (10.9 g, 20.6 mmol).
Mass : [(M+H)+] : 739Mass : [(M+H) + ] : 739
[[ 합성예Synthesis example 8] 화합물8] Compound 15 의15 of 합성 synthesis
3CZO2 (10.9 g, 20.6 mmol)와 (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-3-yl)boronic acid (7.48 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 15 (13.1 g, 수율 78 %)을 얻었다.Except using 3CZO2 (10.9 g, 20.6 mmol) and (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-3-yl)boronic acid (7.48 g, 20.6 mmol) Compound 15 (13.1 g, yield 78%) was obtained by performing the same process as Synthesis Example 1.
Mass : [(M+H)+] : 816Mass : [(M+H) + ] : 816
[[ 합성예Synthesis example 9] 화합물9] Compound 16 의16 of 합성 synthesis
3CZO2 (10.9 g, 20.6 mmol)와 (9-([1,1':3',1''-terphenyl]-5'-yl)-9H-carbazol-3-yl)boronic acid (9.05 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 16 (13.6 g, 수율 74 %)을 얻었다.3CZO2 (10.9 g, 20.6 mmol) and (9-([1,1':3',1''-terphenyl]-5'-yl)-9H-carbazol-3-yl)boronic acid (9.05 g, 20.6 Compound 16 (13.6 g, yield 74%) was obtained by performing the same process as Synthesis Example 1 except for using mmol).
Mass : [(M+H)+] : 892Mass : [(M+H) + ] : 892
[[ 합성예Synthesis example 10] 화합물10] Compound 17 의17 of 합성 synthesis
3CZO3 (10.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 17 (10.6 g, 수율 70 %)을 얻었다.Compound 17 (10.6 g, yield 70%) was obtained by performing the same procedure as Synthesis Example 1 except for using 3CZO3 (10.9 g, 20.6 mmol).
Mass : [(M+H)+] : 739Mass : [(M+H) + ] : 739
[[ 합성예Synthesis example 11] 화합물11] Compound 18 의18 of 합성 synthesis
3CZO3 (10.9 g, 20.6 mmol)와 (9-([1,1'-biphenyl]-3-yl)-9H-carbazol-3-yl)boronic acid (7.48 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 18 (13.3 g, 수율 79 %)을 얻었다.Except using 3CZO3 (10.9 g, 20.6 mmol) and (9-([1,1'-biphenyl]-3-yl)-9H-carbazol-3-yl)boronic acid (7.48 g, 20.6 mmol) performed the same process as Synthesis Example 1 to obtain compound 18 (13.3 g, yield 79%).
Mass : [(M+H)+] : 816Mass : [(M+H) + ] : 816
[[ 합성예Synthesis example 12] 화합물12] Compound 24 의24 합성 synthesis
3CZO3 (10.9 g, 20.6 mmol)와 (9-(phenanthren-2-yl)-9H-carbazol-3-yl)boronic acid (7.98 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 24 (12.6 g, 수율 73 %)을 얻었다.Same process as Synthesis Example 1 except for using 3CZO3 (10.9 g, 20.6 mmol) and (9-(phenanthren-2-yl)-9H-carbazol-3-yl)boronic acid (7.98 g, 20.6 mmol) Compound 24 (12.6 g, yield 73%) was obtained.
Mass : [(M+H)+] : 840Mass : [(M+H) + ] : 840
[[ 합성예Synthesis example 13] 화합물13] Compound 25 의25 of 합성 synthesis
3CZN3 (12.5 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 25 (13.4 g, 수율 80 %)을 얻었다.Compound 25 (13.4 g, yield 80%) was obtained by performing the same procedure as in Synthesis Example 1 except for using 3CZN3 (12.5 g, 20.6 mmol).
Mass : [(M+H)+] : 815Mass : [(M+H) + ] : 815
[[ 합성예Synthesis example 14] 화합물14] Compound 26 의26 of 합성 synthesis
3CZN3 (12.5 g, 20.6 mmol)와 (9-([1,1'-biphenyl]-3-yl)-9H-carbazol-3-yl)boronic acid (7.48 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 26 (13.2 g, 수율 72 %)을 얻었다.Except using 3CZN3 (12.5 g, 20.6 mmol) and (9-([1,1'-biphenyl]-3-yl)-9H-carbazol-3-yl)boronic acid (7.48 g, 20.6 mmol) Compound 26 (13.2 g, yield 72%) was obtained by performing the same process as Synthesis Example 1.
Mass : [(M+H)+] : 891Mass : [(M+H) + ] : 891
[[ 합성예Synthesis example 15] 화합물15] Compound 33 의33 합성 synthesis
3CZN3 (12.5 g, 20.6 mmol)와 (9-(naphthalen-1-yl)-9H-carbazol-3-yl)boronic acid (6.95 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 33 (13.2 g, 수율 74 %)을 얻었다.Same process as Synthesis Example 1 except for using 3CZN3 (12.5 g, 20.6 mmol) and (9-(naphthalen-1-yl)-9H-carbazol-3-yl)boronic acid (6.95 g, 20.6 mmol) Compound 33 (13.2 g, yield 74%) was obtained.
Mass : [(M+H)+] : 865Mass : [(M+H) + ] : 865
[[ 합성예Synthesis example 16] 화합물16] Compound 29 의29 of 합성 synthesis
3CZN2 (12.5 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 29 (11.6 g, 수율 69 %)을 얻었다.Compound 29 (11.6 g, yield 69%) was obtained by performing the same procedure as in Synthesis Example 1 except for using 3CZN2 (12.5 g, 20.6 mmol).
Mass : [(M+H)+] : 815Mass : [(M+H) + ] : 815
[[ 합성예Synthesis example 17] 화합물17] Compound 31 의31 of 합성 synthesis
3CZN2 (12.5 g, 20.6 mmol)와 (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-3-yl)boronic acid (7.48 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 31 (14.1 g, 수율 77 %)을 얻었다.Except using 3CZN2 (12.5 g, 20.6 mmol) and (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-3-yl)boronic acid (7.48 g, 20.6 mmol). performed the same process as Synthesis Example 1 to obtain compound 31 (14.1 g, yield 77%).
Mass : [(M+H)+] : 891Mass : [(M+H) + ] : 891
[[ 합성예Synthesis example 18] 화합물18] Compound 35 의35 of 합성 synthesis
3CZN2 (12.5 g, 20.6 mmol)와 (9-(naphthalen-1-yl)-9H-carbazol-3-yl)boronic acid (6.95 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 35 (12.8 g, 수율 72 %)을 얻었다.Same process as Synthesis Example 1 except for using 3CZN2 (12.5 g, 20.6 mmol) and (9-(naphthalen-1-yl)-9H-carbazol-3-yl)boronic acid (6.95 g, 20.6 mmol) Compound 35 (12.8 g, yield 72%) was obtained.
Mass : [(M+H)+] : 865Mass : [(M+H) + ] : 865
[[ 합성예Synthesis example 19] 화합물19] Compound 37 의37 of 합성 synthesis
3CZS2 (11.3 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 37 (11.5 g, 수율 74 %)을 얻었다.Compound 37 (11.5 g, yield 74%) was obtained by performing the same procedure as in Synthesis Example 1 except for using 3CZS2 (11.3 g, 20.6 mmol).
Mass : [(M+H)+] : 755Mass : [(M+H) + ] : 755
[[ 합성예Synthesis example 20] 화합물20] Compound 39 의39 of 합성 synthesis
3CZS2 (11.3 g, 20.6 mmol)와 (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-3-yl)boronic acid (7.48 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 39 (12.3 g, 수율 72 %)을 얻었다.Except using 3CZS2 (11.3 g, 20.6 mmol) and (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-3-yl)boronic acid (7.48 g, 20.6 mmol) performed the same process as Synthesis Example 1 to obtain compound 39 (12.3 g, yield 72%).
Mass : [(M+H)+] : 832Mass : [(M+H) + ] : 832
[[ 합성예Synthesis example 21] 화합물21] Compound 40 의40 of 합성 synthesis
3CZS2 (11.3 g, 20.6 mmol)와 (9-(triphenylen-2-yl)-9H-carbazol-3-yl)boronic acid (9.01 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 40 (14.7 g, 수율 79 %)을 얻었다.Same process as Synthesis Example 1 except for using 3CZS2 (11.3 g, 20.6 mmol) and (9-(triphenylen-2-yl)-9H-carbazol-3-yl)boronic acid (9.01 g, 20.6 mmol) Compound 40 (14.7 g, yield 79%) was obtained.
Mass : [(M+H)+] : 906Mass : [(M+H) + ] : 906
[[ 합성예Synthesis example 22] 화합물22] Compound 41 의41 of 합성 synthesis
3CZS3 (11.3 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 41 (11.5 g, 수율 74 %)을 얻었다.Compound 41 (11.5 g, yield 74%) was obtained by performing the same procedure as in Synthesis Example 1 except for using 3CZS3 (11.3 g, 20.6 mmol).
Mass : [(M+H)+] : 755Mass : [(M+H) + ] : 755
[[ 합성예Synthesis example 23] 화합물23] Compound 42 의42 of 합성 synthesis
3CZS3 (11.3 g, 20.6 mmol)와 (9-([1,1'-biphenyl]-3-yl)-9H-carbazol-3-yl)boronic acid (7.48 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 42 (12.8 g, 수율 75 %)을 얻었다.Except using 3CZS3 (11.3 g, 20.6 mmol) and (9-([1,1'-biphenyl]-3-yl)-9H-carbazol-3-yl)boronic acid (7.48 g, 20.6 mmol) Compound 42 (12.8 g, yield 75%) was obtained by performing the same process as Synthesis Example 1.
Mass : [(M+H)+] : 832Mass : [(M+H) + ] : 832
[[ 합성예Synthesis example 24] 화합물24] Compound 48 의48 of 합성 synthesis
3CZS3 (11.3 g, 20.6 mmol)와 (9-(phenanthren-2-yl)-9H-carbazol-3-yl)boronic acid (7.98 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 48 (12.6 g, 수율 72 %)을 얻었다.Same process as Synthesis Example 1 except for using 3CZS3 (11.3 g, 20.6 mmol) and (9-(phenanthren-2-yl)-9H-carbazol-3-yl)boronic acid (7.98 g, 20.6 mmol) Compound 48 (12.6 g, yield 72%) was obtained.
Mass : [(M+H)+] : 856Mass : [(M+H) + ] : 856
[[ 합성예Synthesis example 25] 화합물25] Compound 49 의49 of 합성 synthesis
3CZOO2 (7.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 49 (9.0 g, 수율 74 %)을 얻었다.Compound 49 (9.0 g, yield 74%) was obtained by performing the same procedure as Synthesis Example 1 except for using 3CZOO2 (7.9 g, 20.6 mmol).
Mass : [(M+H)+] : 591Mass : [(M+H) + ] : 591
[[ 합성예Synthesis example 26] 화합물26] Compound 50 의50 of 합성 synthesis
3CZOO2 (7.9 g, 20.6 mmol)와 (9-([1,1'-biphenyl]-3-yl)-9H-carbazol-3-yl)boronic acid (7.48 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 50 (9.9 g, 수율 72 %)을 얻었다.Except using 3CZOO2 (7.9 g, 20.6 mmol) and (9-([1,1'-biphenyl]-3-yl)-9H-carbazol-3-yl)boronic acid (7.48 g, 20.6 mmol) Compound 50 (9.9 g, yield 72%) was obtained by performing the same process as Synthesis Example 1.
Mass : [(M+H)+] : 667Mass : [(M+H) + ] : 667
[[ 합성예Synthesis example 27] 화합물27] Compound 53 의53 of 합성 synthesis
3CZOO1 (7.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 53 (9.4 g, 수율 77 %)을 얻었다.Compound 53 (9.4 g, yield 77%) was obtained by performing the same procedure as Synthesis Example 1 except for using 3CZOO1 (7.9 g, 20.6 mmol).
Mass : [(M+H)+] : 591Mass : [(M+H) + ] : 591
[[ 합성예Synthesis example 28] 화합물28] Compound 56 의56 of 합성 synthesis
3CZOO1 (7.9 g, 20.6 mmol)와 (9-(triphenylen-2-yl)-9H-carbazol-3-yl)boronic acid (9.01 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 56 (11.9 g, 수율 78 %)을 얻었다.Same process as Synthesis Example 1 except for using 3CZOO1 (7.9 g, 20.6 mmol) and (9-(triphenylen-2-yl)-9H-carbazol-3-yl)boronic acid (9.01 g, 20.6 mmol) Compound 56 (11.9 g, yield 78%) was obtained.
Mass : [(M+H)+] : 741Mass : [(M+H) + ] : 741
[[ 합성예Synthesis example 29] 화합물29] Compound 57 의57 of 합성 synthesis
3CZF3 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-2-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 57 (11.4 g, 수율 72 %)을 얻었다.Compound 57 ( 11.4 g, yield 72%) was obtained.
Mass : [(M+H)+] : 765Mass : [(M+H) + ] : 765
[[ 합성예Synthesis example 30] 화합물30] Compound 58 의58 of 합성 synthesis
3CZF3 (11.5 g, 20.6 mmol)와 (9-([1,1'-biphenyl]-3-yl)-9H-carbazol-2-yl)boronic acid (7.48 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 58 (12.1 g, 수율 70 %)을 얻었다.Except using 3CZF3 (11.5 g, 20.6 mmol) and (9-([1,1'-biphenyl]-3-yl)-9H-carbazol-2-yl)boronic acid (7.48 g, 20.6 mmol) performed the same process as Synthesis Example 1 to obtain compound 58 (12.1 g, yield 70%).
Mass : [(M+H)+] : 842Mass : [(M+H) + ] : 842
[[ 합성예Synthesis example 31] 화합물31] Compound 65 의65 of 합성 synthesis
3CZF2 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-2-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 65 (11.2 g, 수율 71 %)을 얻었다.Compound 65 ( 11.2 g, yield 71%) was obtained.
Mass : [(M+H)+] : 765Mass : [(M+H) + ] : 765
[[ 합성예Synthesis example 32] 화합물32] Compound 67 의67 of 합성 synthesis
3CZF2 (11.5 g, 20.6 mmol)와 (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-2-yl)boronic acid (7.48 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 67 (11.8 g, 수율 68 %)을 얻었다.Except using 3CZF2 (11.5 g, 20.6 mmol) and (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-2-yl)boronic acid (7.48 g, 20.6 mmol) performed the same process as Synthesis Example 1 to obtain compound 67 (11.8 g, yield 68%).
Mass : [(M+H)+] : 842Mass : [(M+H) + ] : 842
[[ 합성예Synthesis example 33] 화합물33] Compound 69 의69 of 합성 synthesis
3CZO2 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-2-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 69 (10.6 g, 수율 70 %)을 얻었다.Compound 69 ( 10.6 g, yield 70%) was obtained.
Mass : [(M+H)+] : 789Mass : [(M+H) + ] : 789
[[ 합성예Synthesis example 34] 화합물34] Compound 77 의77 of 합성 synthesis
3CZO2 (11.5 g, 20.6 mmol)와 (9-(naphthalen-2-yl)-9H-carbazol-2-yl)boronic acid (6.95 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 77 (11.7 g, 수율 72 %)을 얻었다.Same process as Synthesis Example 1 except for using 3CZO2 (11.5 g, 20.6 mmol) and (9-(naphthalen-2-yl)-9H-carbazol-2-yl)boronic acid (6.95 g, 20.6 mmol) Compound 77 (11.7 g, yield 72%) was obtained.
Mass : [(M+H)+] : 739Mass : [(M+H) + ] : 739
[[ 합성예Synthesis example 35] 화합물35] Compound 73 의73 of 합성 synthesis
3CZO3 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-2-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 73 (10.1 g, 수율 66 %)을 얻었다.Compound 73 ( 10.1 g, yield 66%) was obtained.
Mass : [(M+H)+] : 765Mass : [(M+H) + ] : 765
[[ 합성예Synthesis example 36] 화합물36] Compound 80 의80 of 합성 synthesis
3CZO3 (11.5 g, 20.6 mmol)와 (9-(phenanthren-2-yl)-9H-carbazol-2-yl)boronic acid (7.98 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 80 (10.9 g, 수율 63 %)을 얻었다.Same process as Synthesis Example 1 except for using 3CZO3 (11.5 g, 20.6 mmol) and (9-(phenanthren-2-yl)-9H-carbazol-2-yl)boronic acid (7.98 g, 20.6 mmol) Compound 80 (10.9 g, yield 63%) was obtained.
Mass : [(M+H)+] : 740Mass : [(M+H) + ] : 740
[[ 합성예Synthesis example 37] 화합물37] Compound 81 의81 of 합성 synthesis
3CZN3 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-2-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 81 (12.2 g, 수율 73 %)을 얻었다.Compound 81 ( 12.2 g, yield 73%) was obtained.
Mass : [(M+H)+] : 815Mass : [(M+H) + ] : 815
[[ 합성예Synthesis example 38] 화합물38] Compound 84 의84 of 합성 synthesis
3CZN3 (11.5 g, 20.6 mmol)와 (9-([1,1':3',1''-terphenyl]-5'-yl)-9H-carbazol-2-yl)boronic acid (9.05 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 84 (14.1 g, 수율 71 %)을 얻었다.3CZN3 (11.5 g, 20.6 mmol) and (9-([1,1':3',1''-terphenyl]-5'-yl)-9H-carbazol-2-yl)boronic acid (9.05 g, 20.6 Compound 84 (14.1 g, yield 71%) was obtained by performing the same process as Synthesis Example 1 except for using mmol).
Mass : [(M+H)+] : 967Mass : [(M+H) + ] : 967
[[ 합성예Synthesis example 39] 화합물39] Compound 85 의85 of 합성 synthesis
3CZN2 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-2-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 85 (11.7 g, 수율 70 %)을 얻었다.Compound 85 ( 11.7 g, yield 70%) was obtained.
Mass : [(M+H)+] : 815Mass : [(M+H) + ] : 815
[[ 합성예Synthesis example 40] 화합물40] Compound 92 의92 of 합성 synthesis
3CZN2 (11.5 g, 20.6 mmol)와 (9-(triphenylen-2-yl)-9H-carbazol-2-yl)boronic acid (9.01 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 92 (13.7 g, 수율 69 %)을 얻었다.Same process as Synthesis Example 1 except for using 3CZN2 (11.5 g, 20.6 mmol) and (9-(triphenylen-2-yl)-9H-carbazol-2-yl)boronic acid (9.01 g, 20.6 mmol) Compound 92 (13.7 g, yield 69%) was obtained.
Mass : [(M+H)+] : 965Mass : [(M+H) + ] : 965
[[ 합성예Synthesis example 41] 화합물41] Compound 93 의93 of 합성 synthesis
3CZS2 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-2-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 93 (11.2 g, 수율 72 %)을 얻었다.Compound 93 ( 11.2 g, yield 72%) was obtained.
Mass : [(M+H)+] : 755Mass : [(M+H) + ] : 755
[[ 합성예Synthesis example 42] 화합물42] Compound 101 의101 of 합성 synthesis
3CZS2 (11.5 g, 20.6 mmol)와 (9-(naphthalen-1-yl)-9H-carbazol-2-yl)boronic acid (6.95 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 101 (11.6 g, 수율 70 %)을 얻었다.Same process as Synthesis Example 1 except for using 3CZS2 (11.5 g, 20.6 mmol) and (9-(naphthalen-1-yl)-9H-carbazol-2-yl)boronic acid (6.95 g, 20.6 mmol) Compound 101 (11.6 g, yield 70%) was obtained.
Mass : [(M+H)+] : 806Mass : [(M+H) + ] : 806
[[ 합성예Synthesis example 43] 화합물43] Compound 97 의97 of 합성 synthesis
3CZS3 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-2-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 97 (11.2 g, 수율 72 %)을 얻었다.Compound 97 ( 11.2 g, yield 72%) was obtained.
Mass : [(M+H)+] : 755Mass : [(M+H) + ] : 755
[[ 합성예Synthesis example 44] 화합물44] Compound 99 의99 of 합성 synthesis
3CZS3 (11.5 g, 20.6 mmol)와 (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-2-yl)boronic acid (7.48 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 99 (12.2 g, 수율 71 %)을 얻었다.Except using 3CZS3 (11.5 g, 20.6 mmol) and (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-2-yl)boronic acid (7.48 g, 20.6 mmol) performed the same process as Synthesis Example 1 to obtain compound 99 (12.2 g, yield 71%).
Mass : [(M+H)+] : 832Mass : [(M+H) + ] : 832
[[ 합성예Synthesis example 45] 화합물45] Compound 105 의105 of 합성 synthesis
3CZOO2 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-2-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 105 (8.9 g, 수율 73 %)을 얻었다.Compound 105 ( 8.9 g, yield 73%) was obtained.
Mass : [(M+H)+] : 591Mass : [(M+H) + ] : 591
[[ 합성예Synthesis example 46] 화합물46] Compound 106 의106 of 합성 synthesis
3CZOO2 (11.5 g, 20.6 mmol)와 (9-([1,1'-biphenyl]-3-yl)-9H-carbazol-2-yl)boronic acid (7.48 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 106 (9.8 g, 수율 71 %)을 얻었다.Except using 3CZOO2 (11.5 g, 20.6 mmol) and (9-([1,1'-biphenyl]-3-yl)-9H-carbazol-2-yl)boronic acid (7.48 g, 20.6 mmol) performed the same process as Synthesis Example 1 to obtain compound 106 (9.8 g, yield 71%).
Mass : [(M+H)+] : 667Mass : [(M+H) + ] : 667
[[ 합성예Synthesis example 47] 화합물47] Compound 109 의109 of 합성 synthesis
3CZOO1 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-2-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 109 (8.5 g, 수율 70 %)을 얻었다.Compound 109 ( 8.5 g, yield 70%) was obtained.
Mass : [(M+H)+] : 591Mass : [(M+H) + ] : 591
[[ 합성예Synthesis example 48] 화합물48] Compound 111 의111 of 합성 synthesis
3CZOO1 (11.5 g, 20.6 mmol)와 (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-2-yl)boronic acid (7.48 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 111 (9.5 g, 수율 69 %)을 얻었다.Except using 3CZOO1 (11.5 g, 20.6 mmol) and (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-2-yl)boronic acid (7.48 g, 20.6 mmol) performed the same process as Synthesis Example 1 to obtain compound 111 (9.5 g, yield 69%).
Mass : [(M+H)+] : 667Mass : [(M+H) + ] : 667
[[ 합성예Synthesis example 49] 화합물49] Compound 113 의113 합성 synthesis
3CZF3 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-1-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 113 (9.5 g, 수율 60 %)을 얻었다.Compound 113 ( 9.5 g, yield 60%) was obtained.
Mass : [(M+H)+] : 765Mass : [(M+H) + ] : 765
[[ 합성예Synthesis example 50] 화합물50] Compound 114 의114 합성 synthesis
3CZF3 (11.5 g, 20.6 mmol)와 (9-([1,1'-biphenyl]-3-yl)-9H-carbazol-1-yl)boronic acid (7.48 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 114 (10.1 g, 수율 58 %)을 얻었다.Except using 3CZF3 (11.5 g, 20.6 mmol) and (9-([1,1'-biphenyl]-3-yl)-9H-carbazol-1-yl)boronic acid (7.48 g, 20.6 mmol) performed the same process as Synthesis Example 1 to obtain compound 114 (10.1 g, yield 58%).
Mass : [(M+H)+] : 842Mass : [(M+H) + ] : 842
[[ 합성예Synthesis example 51] 화합물51] Compound 121 의121 of 합성 synthesis
3CZF2 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-1-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 121 (9.3 g, 수율 57 %)을 얻었다.Compound 121 ( 9.3 g, yield 57%) was obtained.
Mass : [(M+H)+] : 765Mass : [(M+H) + ] : 765
[[ 합성예Synthesis example 52] 화합물52] Compound 123 의123 합성 synthesis
3CZF2 (11.5 g, 20.6 mmol)와 (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-1-yl)boronic acid (7.48 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 123 (9.9 g, 수율 57 %)을 얻었다.Except using 3CZF2 (11.5 g, 20.6 mmol) and (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-1-yl)boronic acid (7.48 g, 20.6 mmol) performed the same process as Synthesis Example 1 to obtain compound 123 (9.9 g, yield 57%).
Mass : [(M+H)+] : 842Mass : [(M+H) + ] : 842
[[ 합성예Synthesis example 53] 화합물53] Compound 125 의125 of 합성 synthesis
3CZO2 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-1-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 125 (9.4 g, 수율 62 %)을 얻었다.Compound 125 ( 9.4 g, yield 62%) was obtained.
Mass : [(M+H)+] : 789Mass : [(M+H) + ] : 789
[[ 합성예Synthesis example 54] 화합물54] Compound 133 의133 합성 synthesis
3CZO2 (11.5 g, 20.6 mmol)와 (9-(naphthalen-2-yl)-9H-carbazol-1-yl)boronic acid (6.95 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 133 (10.2 g, 수율 63 %)을 얻었다.Same process as Synthesis Example 1 except for using 3CZO2 (11.5 g, 20.6 mmol) and (9-(naphthalen-2-yl)-9H-carbazol-1-yl)boronic acid (6.95 g, 20.6 mmol) Compound 133 (10.2 g, yield 63%) was obtained.
Mass : [(M+H)+] : 739Mass : [(M+H) + ] : 739
[[ 합성예Synthesis example 55] 화합물55] Compound 129 의129 합성 synthesis
3CZO3 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-1-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 129 (8.9 g, 수율 59 %)을 얻었다.Compound 129 ( 8.9 g, yield 59%) was obtained.
Mass : [(M+H)+] : 765Mass : [(M+H) + ] : 765
[[ 합성예Synthesis example 56] 화합물56] Compound 136 의136 합성 synthesis
3CZO3 (11.5 g, 20.6 mmol)와 (9-(phenanthren-2-yl)-9H-carbazol-1-yl)boronic acid (7.98 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 136 (9.5 g, 수율 55 %)을 얻었다.Same process as Synthesis Example 1 except for using 3CZO3 (11.5 g, 20.6 mmol) and (9-(phenanthren-2-yl)-9H-carbazol-1-yl)boronic acid (7.98 g, 20.6 mmol) Compound 136 (9.5 g, yield 55%) was obtained.
Mass : [(M+H)+] : 740Mass : [(M+H) + ] : 740
[[ 합성예Synthesis example 57] 화합물57] Compound 137 의137 합성 synthesis
3CZN3 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-1-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 137 (9.5 g, 수율 57 %)을 얻었다.Compound 137 ( 9.5 g, yield 57%) was obtained.
Mass : [(M+H)+] : 815Mass : [(M+H) + ] : 815
[[ 합성예Synthesis example 58] 화합물58] Compound 140 의140 of 합성 synthesis
3CZN3 (11.5 g, 20.6 mmol)와 (9-([1,1':3',1''-terphenyl]-3-yl)-9H-carbazol-1-yl)boronic acid (9.05 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 140 (11.7 g, 수율 59 %)을 얻었다.3CZN3 (11.5 g, 20.6 mmol) and (9-([1,1':3',1''-terphenyl]-3-yl)-9H-carbazol-1-yl)boronic acid (9.05 g, 20.6 mmol) ) was performed in the same manner as in Synthesis Example 1, except that Compound 140 (11.7 g, yield 59%) was obtained.
Mass : [(M+H)+] : 967Mass : [(M+H) + ] : 967
[[ 합성예Synthesis example 59] 화합물59] Compound 141 의141 of 합성 synthesis
3CZN2 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-1-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 141 (9.2 g, 수율 55 %)을 얻었다.Compound 141 ( 9.2 g, yield 55%) was obtained.
Mass : [(M+H)+] : 815Mass : [(M+H) + ] : 815
[[ 합성예Synthesis example 60] 화합물60] Compound 148 의148 합성 synthesis
3CZN2 (11.5 g, 20.6 mmol)와 (9-(triphenylen-2-yl)-9H-carbazol-1-yl)boronic acid (9.01 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 148 (11.2 g, 수율 56 %)을 얻었다.Same process as Synthesis Example 1 except for using 3CZN2 (11.5 g, 20.6 mmol) and (9-(triphenylen-2-yl)-9H-carbazol-1-yl)boronic acid (9.01 g, 20.6 mmol) Compound 148 (11.2 g, yield 56%) was obtained.
Mass : [(M+H)+] : 965Mass : [(M+H) + ] : 965
[[ 합성예Synthesis example 61] 화합물61] Compound 149 의149 of 합성 synthesis
3CZS2 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-1-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 149 (9.6 g, 수율 62 %)을 얻었다.Compound 149 ( 9.6 g, yield 62%) was obtained.
Mass : [(M+H)+] : 755Mass : [(M+H) + ] : 755
[[ 합성예Synthesis example 62] 화합물62] Compound 157 의157 of 합성 synthesis
3CZS2 (11.5 g, 20.6 mmol)와 (9-(naphthalen-1-yl)-9H-carbazol-1-yl)boronic acid (6.95 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 157 (9.9 g, 수율 60 %)을 얻었다.Same process as Synthesis Example 1 except for using 3CZS2 (11.5 g, 20.6 mmol) and (9-(naphthalen-1-yl)-9H-carbazol-1-yl)boronic acid (6.95 g, 20.6 mmol) Compound 157 (9.9 g, yield 60%) was obtained.
Mass : [(M+H)+] : 806Mass : [(M+H) + ] : 806
[[ 합성예Synthesis example 63] 화합물63] Compound 153 의153 of 합성 synthesis
3CZS3 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-1-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 153 (9.5 g, 수율 61 %)을 얻었다.Compound 153 ( 9.5 g, yield 61%) was obtained.
Mass : [(M+H)+] : 755Mass : [(M+H) + ] : 755
[[ 합성예Synthesis example 64] 화합물64] Compound 155 의155 of 합성 synthesis
3CZS3 (11.5 g, 20.6 mmol)와 (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-1-yl)boronic acid (7.48 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 155 (10.4 g, 수율 61 %)을 얻었다.Except using 3CZS3 (11.5 g, 20.6 mmol) and (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-1-yl)boronic acid (7.48 g, 20.6 mmol) Compound 155 (10.4 g, yield 61%) was obtained by performing the same process as Synthesis Example 1.
Mass : [(M+H)+] : 832Mass : [(M+H) + ] : 832
[[ 합성예Synthesis example 65] 화합물65] Compound 161 의161 of 합성 synthesis
3CZOO2 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-1-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 161 (7.8 g, 수율 64 %)을 얻었다.Compound 161 ( 7.8 g, yield 64%) was obtained.
Mass : [(M+H)+] : 591Mass : [(M+H) + ] : 591
[[ 합성예Synthesis example 66] 화합물66] Compound 162 의162 of 합성 synthesis
3CZOO2 (11.5 g, 20.6 mmol)와 (9-([1,1'-biphenyl]-3-yl)-9H-carbazol-1-yl)boronic acid (7.48 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 162 (8.5 g, 수율 62 %)을 얻었다.Except using 3CZOO2 (11.5 g, 20.6 mmol) and (9-([1,1'-biphenyl]-3-yl)-9H-carbazol-1-yl)boronic acid (7.48 g, 20.6 mmol) performed the same process as Synthesis Example 1 to obtain compound 162 (8.5 g, yield 62%).
Mass : [(M+H)+] : 667Mass : [(M+H) + ] : 667
[[ 합성예Synthesis example 67] 화합물67] Compound 165 의165 of 합성 synthesis
3CZOO1 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-1-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 165 (7.3 g, 수율 60 %)을 얻었다.Compound 165 ( 7.3 g, yield 60%) was obtained.
Mass : [(M+H)+] : 591Mass : [(M+H) + ] : 591
[[ 합성예Synthesis example 68] 화합물68] Compound 167 의167 of 합성 synthesis
3CZOO1 (11.5 g, 20.6 mmol)와 (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-1-yl)boronic acid (7.48 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 167 (8.1 g, 수율 59 %)을 얻었다.Except using 3CZOO1 (11.5 g, 20.6 mmol) and (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-1-yl)boronic acid (7.48 g, 20.6 mmol) performed the same process as Synthesis Example 1 to obtain compound 167 (8.1 g, yield 59%).
Mass : [(M+H)+] : 667Mass : [(M+H) + ] : 667
[[ 합성예Synthesis example 69] 화합물69] Compound 169 의169 of 합성 synthesis
3CZF3 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-4-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 169 (10.7 g, 수율 68 %)을 얻었다.Compound 169 ( 10.7 g, yield 68%) was obtained.
Mass : [(M+H)+] : 765Mass : [(M+H) + ] : 765
[[ 합성예Synthesis example 70] 화합물70] Compound 170 의170 of 합성 synthesis
3CZF3 (11.5 g, 20.6 mmol)와 (9-([1,1'-biphenyl]-3-yl)-9H-carbazol-4-yl)boronic acid (7.48 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 170 (11.4 g, 수율 66 %)을 얻었다.Except using 3CZF3 (11.5 g, 20.6 mmol) and (9-([1,1'-biphenyl]-3-yl)-9H-carbazol-4-yl)boronic acid (7.48 g, 20.6 mmol) Compound 170 (11.4 g, yield 66%) was obtained by performing the same process as Synthesis Example 1.
Mass : [(M+H)+] : 842Mass : [(M+H) + ] : 842
[[ 합성예Synthesis example 71] 화합물71] Compound 177 의177 of 합성 synthesis
3CZF2 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-4-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 177 (10.1 g, 수율 64 %)을 얻었다.Compound 177 ( 10.1 g, yield 64%) was obtained.
Mass : [(M+H)+] : 765Mass : [(M+H) + ] : 765
[[ 합성예Synthesis example 72] 화합물72] Compound 179 의179 of 합성 synthesis
3CZF2 (11.5 g, 20.6 mmol)와 (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-4-yl)boronic acid (7.48 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 179 (11.3 g, 수율 65 %)을 얻었다.Except using 3CZF2 (11.5 g, 20.6 mmol) and (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-4-yl)boronic acid (7.48 g, 20.6 mmol) performed the same process as Synthesis Example 1 to obtain compound 179 (11.3 g, yield 65%).
Mass : [(M+H)+] : 842Mass : [(M+H) + ] : 842
[[ 합성예Synthesis example 73] 화합물73] Compound 181 의181 of 합성 synthesis
3CZO2 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-4-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 181 (10.2 g, 수율 67 %)을 얻었다.Compound 181 ( 10.2 g, yield 67%) was obtained.
Mass : [(M+H)+] : 789Mass : [(M+H) + ] : 789
[[ 합성예Synthesis example 74] 화합물74] Compound 189 의189 of 합성 synthesis
3CZO2 (11.5 g, 20.6 mmol)와 (9-(naphthalen-2-yl)-9H-carbazol-4-yl)boronic acid (6.95 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 189 (11.5 g, 수율 71 %)을 얻었다.Same process as Synthesis Example 1 except for using 3CZO2 (11.5 g, 20.6 mmol) and (9-(naphthalen-2-yl)-9H-carbazol-4-yl)boronic acid (6.95 g, 20.6 mmol) Compound 189 (11.5 g, yield 71%) was obtained.
Mass : [(M+H)+] : 739Mass : [(M+H) + ] : 739
[[ 합성예Synthesis example 75] 화합물75] Compound 185 의185 of 합성 synthesis
3CZO3 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-4-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 185 (10.6 g, 수율 70 %)을 얻었다.Compound 185 ( 10.6 g, yield 70%) was obtained.
Mass : [(M+H)+] : 765Mass : [(M+H) + ] : 765
[[ 합성예Synthesis example 76] 화합물76] Compound 192 의192 of 합성 synthesis
3CZO3 (11.5 g, 20.6 mmol)와 (9-(phenanthren-2-yl)-9H-carbazol-4-yl)boronic acid (7.98 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 192 (12.4 g, 수율 72 %)을 얻었다.Same process as Synthesis Example 1 except for using 3CZO3 (11.5 g, 20.6 mmol) and (9-(phenanthren-2-yl)-9H-carbazol-4-yl)boronic acid (7.98 g, 20.6 mmol) Compound 192 (12.4 g, yield 72%) was obtained.
Mass : [(M+H)+] : 740Mass : [(M+H) + ] : 740
[[ 합성예Synthesis example 77] 화합물77] Compound 193 의193 of 합성 synthesis
3CZN3 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-4-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 193 (11.6 g, 수율 69 %)을 얻었다.Compound 193 ( 11.6 g, yield 69%) was obtained.
Mass : [(M+H)+] : 815Mass : [(M+H) + ] : 815
[[ 합성예Synthesis example 78] 화합물78] Compound 196 의196 of 합성 synthesis
3CZN3 (11.5 g, 20.6 mmol)와 (9-([1,1':3',1''-terphenyl]-5'-yl)-9H-carbazol-4-yl)boronic acid (9.05 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 196 (12.7 g, 수율 64 %)을 얻었다.3CZN3 (11.5 g, 20.6 mmol) and (9-([1,1':3',1''-terphenyl]-5'-yl)-9H-carbazol-4-yl)boronic acid (9.05 g, 20.6 Compound 196 (12.7 g, yield 64%) was obtained by performing the same process as Synthesis Example 1 except for using mmol).
Mass : [(M+H)+] : 967Mass : [(M+H) + ] : 967
[[ 합성예Synthesis example 79] 화합물79] Compound 197 의197 of 합성 synthesis
3CZN2 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-4-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 197 (11.4 g, 수율 68 %)을 얻었다.Compound 197 ( 11.4 g, yield 68%) was obtained.
Mass : [(M+H)+] : 815Mass : [(M+H) + ] : 815
[[ 합성예Synthesis example 80] 화합물80] Compound 204 의204 of 합성 synthesis
3CZN2 (11.5 g, 20.6 mmol)와 (9-(triphenylen-2-yl)-9H-carbazol-4-yl)boronic acid (9.01 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 204 (13.1 g, 수율 66 %)을 얻었다.Same process as Synthesis Example 1 except for using 3CZN2 (11.5 g, 20.6 mmol) and (9-(triphenylen-2-yl)-9H-carbazol-4-yl)boronic acid (9.01 g, 20.6 mmol) Compound 204 (13.1 g, yield 66%) was obtained.
Mass : [(M+H)+] : 965Mass : [(M+H) + ] : 965
[[ 합성예Synthesis example 81] 화합물81] Compound 205 의205 of 합성 synthesis
3CZS2 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-4-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 205 (9.3 g, 수율 60 %)을 얻었다.Compound 205 ( 9.3 g, yield 60%) was obtained.
Mass : [(M+H)+] : 755Mass : [(M+H) + ] : 755
[[ 합성예Synthesis example 82] 화합물82] Compound 213 의213 of 합성 synthesis
3CZS2 (11.5 g, 20.6 mmol)와 (9-(naphthalen-1-yl)-9H-carbazol-4-yl)boronic acid (6.95 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 213 (11.1 g, 수율 67 %)을 얻었다.Same process as Synthesis Example 1 except for using 3CZS2 (11.5 g, 20.6 mmol) and (9-(naphthalen-1-yl)-9H-carbazol-4-yl)boronic acid (6.95 g, 20.6 mmol) Compound 213 (11.1 g, yield 67%) was obtained.
Mass : [(M+H)+] : 806Mass : [(M+H) + ] : 806
[[ 합성예Synthesis example 83] 화합물83] Compound 209 의209 of 합성 synthesis
3CZS3 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-4-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 209 (10.3 g, 수율 66 %)을 얻었다.Compound 209 ( 10.3 g, yield 66%) was obtained.
Mass : [(M+H)+] : 755Mass : [(M+H) + ] : 755
[[ 합성예Synthesis example 84] 화합물84] Compound 211 의211 of 합성 synthesis
3CZS3 (11.5 g, 20.6 mmol)와 (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-4-yl)boronic acid (7.48 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 211 (10.9 g, 수율 64 %)을 얻었다.Except using 3CZS3 (11.5 g, 20.6 mmol) and (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-4-yl)boronic acid (7.48 g, 20.6 mmol) performed the same process as Synthesis Example 1 to obtain compound 211 (10.9 g, yield 64%).
Mass : [(M+H)+] : 832Mass : [(M+H) + ] : 832
[[ 합성예Synthesis example 85] 화합물85] Compound 217 의217 of 합성 synthesis
3CZOO2 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-4-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 217 (8.8 g, 수율 72 %)을 얻었다.Compound 217 ( 8.8 g, yield 72%) was obtained.
Mass : [(M+H)+] : 591Mass : [(M+H) + ] : 591
[[ 합성예Synthesis example 86] 화합물86] Compound 218 의218 of 합성 synthesis
3CZOO2 (11.5 g, 20.6 mmol)와 (9-([1,1'-biphenyl]-3-yl)-9H-carbazol-4-yl)boronic acid (7.48 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 218 (9.6 g, 수율 70 %)을 얻었다.Except using 3CZOO2 (11.5 g, 20.6 mmol) and (9-([1,1'-biphenyl]-3-yl)-9H-carbazol-4-yl)boronic acid (7.48 g, 20.6 mmol) performed the same process as Synthesis Example 1 to obtain compound 218 (9.6 g, yield 70%).
Mass : [(M+H)+] : 667Mass : [(M+H) + ] : 667
[[ 합성예Synthesis example 87] 화합물87] Compound 221 의221 of 합성 synthesis
3CZOO1 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-4-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 221 (8.4 g, 수율 69 %)을 얻었다.Compound 221 ( 8.4 g, yield 69%) was obtained.
Mass : [(M+H)+] : 591Mass : [(M+H) + ] : 591
[[ 합성예Synthesis example 88] 화합물88] Compound 223 의223 of 합성 synthesis
3CZOO1 (11.5 g, 20.6 mmol)와 (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-4-yl)boronic acid (7.48 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 223 (9.3 g, 수율 68 %)을 얻었다.Except using 3CZOO1 (11.5 g, 20.6 mmol) and (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-4-yl)boronic acid (7.48 g, 20.6 mmol) performed the same process as Synthesis Example 1 to obtain compound 223 (9.3 g, yield 68%).
Mass : [(M+H)+] : 667Mass : [(M+H) + ] : 667
[[ 합성예Synthesis example 89] 화합물89] Compound 225 의225 of 합성 synthesis
2CZF3 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-1-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 225 (9.1 g, 수율 58 %)을 얻었다.Compound 225 ( 9.1 g, yield 58%) was obtained.
Mass : [(M+H)+] : 765Mass : [(M+H) + ] : 765
[[ 합성예Synthesis example 90] 화합물90] Compound 226 의226 of 합성 synthesis
2CZF3 (11.5 g, 20.6 mmol)와 (9-([1,1'-biphenyl]-3-yl)-9H-carbazol-1-yl)boronic acid (7.48 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 226 (9.5 g, 수율 55 %)을 얻었다.Except using 2CZF3 (11.5 g, 20.6 mmol) and (9-([1,1'-biphenyl]-3-yl)-9H-carbazol-1-yl)boronic acid (7.48 g, 20.6 mmol) performed the same process as Synthesis Example 1 to obtain compound 226 (9.5 g, yield 55%).
Mass : [(M+H)+] : 842Mass : [(M+H) + ] : 842
[[ 합성예Synthesis example 91] 화합물91] Compound 233 의233 합성 synthesis
2CZF2 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-1-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 233 (8.9 g, 수율 57 %)을 얻었다.Compound 233 ( 8.9 g, yield 57%) was obtained.
Mass : [(M+H)+] : 765Mass : [(M+H) + ] : 765
[[ 합성예Synthesis example 92] 화합물92] Compound 235 의235 합성 synthesis
2CZF2 (11.5 g, 20.6 mmol)와 (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-1-yl)boronic acid (7.48 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 235 (9.0 g, 수율 52 %)을 얻었다.Except using 2CZF2 (11.5 g, 20.6 mmol) and (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-1-yl)boronic acid (7.48 g, 20.6 mmol) performed the same process as Synthesis Example 1 to obtain compound 235 (9.0 g, yield 52%).
Mass : [(M+H)+] : 842Mass : [(M+H) + ] : 842
[[ 합성예Synthesis example 93] 화합물93] Compound 237 의237 합성 synthesis
2CZO2 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-1-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 237 (7.6 g, 수율 50 %)을 얻었다.Compound 237 ( 7.6 g, yield 50%) was obtained.
Mass : [(M+H)+] : 789Mass : [(M+H) + ] : 789
[[ 합성예Synthesis example 94] 화합물94] Compound 245 의245 합성 synthesis
2CZO2 (11.5 g, 20.6 mmol)와 (9-(naphthalen-2-yl)-9H-carbazol-1-yl)boronic acid (6.95 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 245 (8.5 g, 수율 52 %)을 얻었다.Same process as Synthesis Example 1 except for using 2CZO2 (11.5 g, 20.6 mmol) and (9-(naphthalen-2-yl)-9H-carbazol-1-yl)boronic acid (6.95 g, 20.6 mmol) Compound 245 (8.5 g, yield 52%) was obtained.
Mass : [(M+H)+] : 739Mass : [(M+H) + ] : 739
[[ 합성예Synthesis example 95] 화합물95] Compound 241 의241 합성 synthesis
2CZO3 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-1-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 241 (8.2 g, 수율 54 %)을 얻었다.Compound 241 ( 8.2 g, yield 54%) was obtained.
Mass : [(M+H)+] : 765Mass : [(M+H) + ] : 765
[[ 합성예Synthesis example 96] 화합물96] Compound 248 의248 합성 synthesis
2CZO3 (11.5 g, 20.6 mmol)와 (9-(phenanthren-2-yl)-9H-carbazol-1-yl)boronic acid (7.98 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 248 (9.2 g, 수율 53 %)을 얻었다.Same process as Synthesis Example 1 except for using 2CZO3 (11.5 g, 20.6 mmol) and (9-(phenanthren-2-yl)-9H-carbazol-1-yl)boronic acid (7.98 g, 20.6 mmol) Compound 248 (9.2 g, yield 53%) was obtained.
Mass : [(M+H)+] : 740Mass : [(M+H) + ] : 740
[[ 합성예Synthesis example 97] 화합물97] Compound 249 의249 of 합성 synthesis
2CZN3 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-1-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 249 (9.2 g, 수율 55 %)을 얻었다.Compound 249 ( 9.2 g, yield 55%) was obtained.
Mass : [(M+H)+] : 815Mass : [(M+H) + ] : 815
[[ 합성예Synthesis example 98] 화합물98] Compound 252 의252 of 합성 synthesis
2CZN3 (11.5 g, 20.6 mmol)와 (9-([1,1':3',1''-terphenyl]-3-yl)-9H-carbazol-1-yl)boronic acid (9.05 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 252 (9.9 g, 수율 50 %)을 얻었다.2CZN3 (11.5 g, 20.6 mmol) and (9-([1,1':3',1''-terphenyl]-3-yl)-9H-carbazol-1-yl)boronic acid (9.05 g, 20.6 mmol) ) was used to obtain compound 252 (9.9 g, yield 50%) by performing the same procedure as in Synthesis Example 1.
Mass : [(M+H)+] : 967Mass : [(M+H) + ] : 967
[[ 합성예Synthesis example 99] 화합물99] Compound 253 의253 of 합성 synthesis
2CZN2 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-1-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 253 (8.6 g, 수율 51 %)을 얻었다.Compound 253 ( 8.6 g, yield 51%) was obtained.
Mass : [(M+H)+] : 815Mass : [(M+H) + ] : 815
[[ 합성예Synthesis example 100] 화합물100] Compound 260 의260 of 합성 synthesis
2CZN2 (11.5 g, 20.6 mmol)와 (9-(triphenylen-2-yl)-9H-carbazol-1-yl)boronic acid (9.01 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 260 (10.3 g, 수율 52 %)을 얻었다.The same process as Synthesis Example 1 except for using 2CZN2 (11.5 g, 20.6 mmol) and (9-(triphenylen-2-yl)-9H-carbazol-1-yl)boronic acid (9.01 g, 20.6 mmol) Compound 260 (10.3 g, yield 52%) was obtained.
Mass : [(M+H)+] : 965Mass : [(M+H) + ] : 965
[[ 합성예Synthesis example 101] 화합물101] Compound 261 의261 of 합성 synthesis
2CZS2 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-1-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 261 (8.2 g, 수율 53 %)을 얻었다.Compound 261 ( 8.2 g, yield 53%) was obtained.
Mass : [(M+H)+] : 755Mass : [(M+H) + ] : 755
[[ 합성예Synthesis example 102] 화합물102] Compound 269 의269 of 합성 synthesis
2CZS2 (11.5 g, 20.6 mmol)와 (9-(naphthalen-1-yl)-9H-carbazol-1-yl)boronic acid (6.95 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 269 (8.9 g, 수율 54 %)을 얻었다.The same process as Synthesis Example 1 except for using 2CZS2 (11.5 g, 20.6 mmol) and (9-(naphthalen-1-yl)-9H-carbazol-1-yl)boronic acid (6.95 g, 20.6 mmol) Compound 269 (8.9 g, yield 54%) was obtained.
Mass : [(M+H)+] : 806Mass : [(M+H) + ] : 806
[[ 합성예Synthesis example 103] 화합물103] Compound 265 의265 of 합성 synthesis
2CZS3 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-1-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 265 (8.5 g, 수율 55 %)을 얻었다.Compound 265 ( 8.5 g, yield 55%) was obtained.
Mass : [(M+H)+] : 755Mass : [(M+H) + ] : 755
[[ 합성예Synthesis example 104] 화합물104] Compound 267 의267 합성 synthesis
2CZS3 (11.5 g, 20.6 mmol)와 (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-1-yl)boronic acid (7.48 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 267 (8.6 g, 수율 50 %)을 얻었다.Except using 2CZS3 (11.5 g, 20.6 mmol) and (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-1-yl)boronic acid (7.48 g, 20.6 mmol) performed the same process as Synthesis Example 1 to obtain compound 267 (8.6 g, yield 50%).
Mass : [(M+H)+] : 832Mass : [(M+H) + ] : 832
[[ 합성예Synthesis example 105] 화합물105] Compound 273 의273 합성 synthesis
2CZOO2 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-1-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 273 (6.7 g, 수율 55 %)을 얻었다.Compound 273 ( 6.7 g, yield 55%) was obtained.
Mass : [(M+H)+] : 591Mass : [(M+H) + ] : 591
[[ 합성예Synthesis example 106] 화합물106] Compound 274 의274 합성 synthesis
2CZOO2 (11.5 g, 20.6 mmol)와 (9-([1,1'-biphenyl]-3-yl)-9H-carbazol-1-yl)boronic acid (7.48 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 274 (7.1 g, 수율 52 %)을 얻었다.Except using 2CZOO2 (11.5 g, 20.6 mmol) and (9-([1,1'-biphenyl]-3-yl)-9H-carbazol-1-yl)boronic acid (7.48 g, 20.6 mmol) performed the same process as Synthesis Example 1 to obtain compound 274 (7.1 g, yield 52%).
Mass : [(M+H)+] : 667Mass : [(M+H) + ] : 667
[[ 합성예Synthesis example 107] 화합물107] Compound 277 의277 합성 synthesis
2CZOO1 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-1-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 277 (6.2 g, 수율 51 %)을 얻었다.Compound 277 ( 6.2 g, yield 51%) was obtained.
Mass : [(M+H)+] : 591Mass : [(M+H) + ] : 591
[[ 합성예Synthesis example 108] 화합물108] Compound 279 의279 of 합성 synthesis
2CZOO1 (11.5 g, 20.6 mmol)와 (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-1-yl)boronic acid (7.48 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 279 (7.1 g, 수율 52 %)을 얻었다.Except using 2CZOO1 (11.5 g, 20.6 mmol) and (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-1-yl)boronic acid (7.48 g, 20.6 mmol) performed the same process as Synthesis Example 1 to obtain compound 279 (7.1 g, yield 52%).
Mass : [(M+H)+] : 667Mass : [(M+H) + ] : 667
[[ 합성예Synthesis example 109] 화합물109] Compound 281 의281 of 합성 synthesis
2CZF3 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-2-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 281 (11.0 g, 수율 70 %)을 얻었다.Compound 281 ( 11.0 g, yield 70%) was obtained.
Mass : [(M+H)+] : 765Mass : [(M+H) + ] : 765
[[ 합성예Synthesis example 110] 화합물110] Compound 282 의282 of 합성 synthesis
2CZF3 (11.5 g, 20.6 mmol)와 (9-([1,1'-biphenyl]-3-yl)-9H-carbazol-2-yl)boronic acid (7.48 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 282 (12.5 g, 수율 72 %)을 얻었다.Except using 2CZF3 (11.5 g, 20.6 mmol) and (9-([1,1'-biphenyl]-3-yl)-9H-carbazol-2-yl)boronic acid (7.48 g, 20.6 mmol) performed the same process as Synthesis Example 1 to obtain compound 282 (12.5 g, yield 72%).
Mass : [(M+H)+] : 842Mass : [(M+H) + ] : 842
[[ 합성예Synthesis example 111] 화합물111] Compound 289 의289 of 합성 synthesis
2CZF2 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-2-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 289 (10.7 g, 수율 68 %)을 얻었다.Compound 289 ( 10.7 g, yield 68%) was obtained.
Mass : [(M+H)+] : 765Mass : [(M+H) + ] : 765
[[ 합성예Synthesis example 112] 화합물112] Compound 291 의291 of 합성 synthesis
2CZF2 (11.5 g, 20.6 mmol)와 (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-2-yl)boronic acid (7.48 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 291 (11.9 g, 수율 69 %)을 얻었다.Except using 2CZF2 (11.5 g, 20.6 mmol) and (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-2-yl)boronic acid (7.48 g, 20.6 mmol) performed the same process as Synthesis Example 1 to obtain compound 291 (11.9 g, yield 69%).
Mass : [(M+H)+] : 842Mass : [(M+H) + ] : 842
[[ 합성예Synthesis example 113] 화합물113] Compound 293 의293 of 합성 synthesis
2CZO2 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-2-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 293 (10.0 g, 수율 66 %)을 얻었다.Compound 293 ( 10.0 g, yield 66%) was obtained.
Mass : [(M+H)+] : 789Mass : [(M+H) + ] : 789
[[ 합성예Synthesis example 114] 화합물114] Compound 301 의301 of 합성 synthesis
2CZO2 (11.5 g, 20.6 mmol)와 (9-(naphthalen-2-yl)-9H-carbazol-2-yl)boronic acid (6.95 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 301 (10.0 g, 수율 62 %)을 얻었다.Same process as Synthesis Example 1 except for using 2CZO2 (11.5 g, 20.6 mmol) and (9-(naphthalen-2-yl)-9H-carbazol-2-yl)boronic acid (6.95 g, 20.6 mmol) Compound 301 (10.0 g, yield 62%) was obtained.
Mass : [(M+H)+] : 739Mass : [(M+H) + ] : 739
[[ 합성예Synthesis example 115] 화합물115] Compound 297 의297 of 합성 synthesis
2CZO3 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-2-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 297 (10.4 g, 수율 68 %)을 얻었다.Compound 297 ( 10.4 g, yield 68%) was obtained.
Mass : [(M+H)+] : 765Mass : [(M+H) + ] : 765
[[ 합성예Synthesis example 116] 화합물116] Compound 304 의304 of 합성 synthesis
2CZO3 (11.5 g, 20.6 mmol)와 (9-(phenanthren-2-yl)-9H-carbazol-2-yl)boronic acid (7.98 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 304 (11.1 g, 수율 64 %)을 얻었다.Same process as Synthesis Example 1 except for using 2CZO3 (11.5 g, 20.6 mmol) and (9-(phenanthren-2-yl)-9H-carbazol-2-yl)boronic acid (7.98 g, 20.6 mmol) Compound 304 (11.1 g, yield 64%) was obtained.
Mass : [(M+H)+] : 740Mass : [(M+H) + ] : 740
[[ 합성예Synthesis example 117] 화합물117] Compound 305 의305 of 합성 synthesis
2CZN3 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-2-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 305 (12.2 g, 수율 73 %)을 얻었다.Compound 305 ( 12.2 g, yield 73%) was obtained.
Mass : [(M+H)+] : 815Mass : [(M+H) + ] : 815
[[ 합성예Synthesis example 118] 화합물118] Compound 308 의308 of 합성 synthesis
2CZN3 (11.5 g, 20.6 mmol)와 (9-([1,1':3',1''-terphenyl]-5'-yl)-9H-carbazol-2-yl)boronic acid (9.05 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 308 (14.3 g, 수율 72 %)을 얻었다.2CZN3 (11.5 g, 20.6 mmol) and (9-([1,1':3',1''-terphenyl]-5'-yl)-9H-carbazol-2-yl)boronic acid (9.05 g, 20.6 Compound 308 (14.3 g, yield 72%) was obtained by performing the same process as Synthesis Example 1 except for using mmol).
Mass : [(M+H)+] : 967Mass : [(M+H) + ] : 967
[[ 합성예Synthesis example 119] 화합물119] Compound 309 의309 of 합성 synthesis
2CZN2 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-2-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 309 (11.7 g, 수율 70 %)을 얻었다.Compound 309 ( 11.7 g, yield 70%) was obtained.
Mass : [(M+H)+] : 815Mass : [(M+H) + ] : 815
[[ 합성예Synthesis example 120] 화합물120] Compound 316 의316 합성 synthesis
2CZN2 (11.5 g, 20.6 mmol)와 (9-(triphenylen-2-yl)-9H-carbazol-2-yl)boronic acid (9.01 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 316 (14.1 g, 수율 71 %)을 얻었다.The same process as Synthesis Example 1 except for using 2CZN2 (11.5 g, 20.6 mmol) and (9-(triphenylen-2-yl)-9H-carbazol-2-yl)boronic acid (9.01 g, 20.6 mmol) Compound 316 (14.1 g, yield 71%) was obtained.
Mass : [(M+H)+] : 965Mass : [(M+H) + ] : 965
[[ 합성예Synthesis example 121] 화합물121] Compound 317 의317 합성 synthesis
2CZS2 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-2-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 317 (11.5 g, 수율 74 %)을 얻었다.Compound 317 ( 11.5 g, yield 74%) was obtained.
Mass : [(M+H)+] : 755Mass : [(M+H) + ] : 755
[[ 합성예Synthesis example 122] 화합물122] Compound 325 의325 합성 synthesis
2CZS2 (11.5 g, 20.6 mmol)와 (9-(naphthalen-1-yl)-9H-carbazol-2-yl)boronic acid (6.95 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 325 (11.9 g, 수율 72 %)을 얻었다.The same process as Synthesis Example 1 except for using 2CZS2 (11.5 g, 20.6 mmol) and (9-(naphthalen-1-yl)-9H-carbazol-2-yl)boronic acid (6.95 g, 20.6 mmol) Compound 325 (11.9 g, yield 72%) was obtained.
Mass : [(M+H)+] : 806Mass : [(M+H) + ] : 806
[[ 합성예Synthesis example 123] 화합물123] Compound 321 의321 합성 synthesis
2CZS3 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-2-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 321 (10.9 g, 수율 70 %)을 얻었다.Compound 321 ( 10.9 g, yield 70%) was obtained.
Mass : [(M+H)+] : 755Mass : [(M+H) + ] : 755
[[ 합성예Synthesis example 124] 화합물124] Compound 323 의323 합성 synthesis
2CZS3 (11.5 g, 20.6 mmol)와 (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-2-yl)boronic acid (7.48 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 323 (11.6 g, 수율 68 %)을 얻었다.Except using 2CZS3 (11.5 g, 20.6 mmol) and (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-2-yl)boronic acid (7.48 g, 20.6 mmol) performed the same process as Synthesis Example 1 to obtain compound 323 (11.6 g, yield 68%).
Mass : [(M+H)+] : 832Mass : [(M+H) + ] : 832
[[ 합성예Synthesis example 125] 화합물125] Compound 329 의329 of 합성 synthesis
2CZOO2 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-2-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 329 (8.3 g, 수율 68 %)을 얻었다.Compound 329 ( 8.3 g, yield 68%) was obtained.
Mass : [(M+H)+] : 591Mass : [(M+H) + ] : 591
[[ 합성예Synthesis example 126] 화합물126] Compound 330 의330 of 합성 synthesis
2CZOO2 (11.5 g, 20.6 mmol)와 (9-([1,1'-biphenyl]-3-yl)-9H-carbazol-2-yl)boronic acid (7.48 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 330 (9.6 g, 수율 70 %)을 얻었다.Except using 2CZOO2 (11.5 g, 20.6 mmol) and (9-([1,1'-biphenyl]-3-yl)-9H-carbazol-2-yl)boronic acid (7.48 g, 20.6 mmol) performed the same process as Synthesis Example 1 to obtain compound 330 (9.6 g, yield 70%).
Mass : [(M+H)+] : 667Mass : [(M+H) + ] : 667
[[ 합성예Synthesis example 127] 화합물127] Compound 333 의333 합성 synthesis
2CZOO1 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-2-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 333 (8.4 g, 수율 69 %)을 얻었다.Compound 333 ( 8.4 g, yield 69%) was obtained.
Mass : [(M+H)+] : 591Mass : [(M+H) + ] : 591
[[ 합성예Synthesis example 128] 화합물128] Compound 335 의335 합성 synthesis
2CZOO1 (11.5 g, 20.6 mmol)와 (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-2-yl)boronic acid (7.48 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 335 (9.1 g, 수율 66 %)을 얻었다.Except using 2CZOO1 (11.5 g, 20.6 mmol) and (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-2-yl)boronic acid (7.48 g, 20.6 mmol) performed the same process as Synthesis Example 1 to obtain compound 335 (9.1 g, yield 66%).
Mass : [(M+H)+] : 667Mass : [(M+H) + ] : 667
[[ 합성예Synthesis example 129] 화합물129] Compound 337 의337 합성 synthesis
2CZF3 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-3-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 337 (12.1 g, 수율 77 %)을 얻었다.Compound 337 ( 12.1 g, yield 77%) was obtained.
Mass : [(M+H)+] : 765Mass : [(M+H) + ] : 765
[[ 합성예Synthesis example 130] 화합물130] Compound 338 의338 합성 synthesis
2CZF3 (11.5 g, 20.6 mmol)와 (9-([1,1'-biphenyl]-3-yl)-9H-carbazol-3-yl)boronic acid (7.48 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 338 (13.0 g, 수율 75 %)을 얻었다.Except using 2CZF3 (11.5 g, 20.6 mmol) and (9-([1,1'-biphenyl]-3-yl)-9H-carbazol-3-yl)boronic acid (7.48 g, 20.6 mmol) performed the same process as Synthesis Example 1 to obtain compound 338 (13.0 g, yield 75%).
Mass : [(M+H)+] : 842Mass : [(M+H) + ] : 842
[[ 합성예Synthesis example 131] 화합물131] Compound 345 의345 합성 synthesis
2CZF2 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-3-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 345 (12.5 g, 수율 79 %)을 얻었다.Compound 345 ( 12.5 g, yield 79%) was obtained.
Mass : [(M+H)+] : 765Mass : [(M+H) + ] : 765
[[ 합성예Synthesis example 132] 화합물132] Compound 347 의347 합성 synthesis
2CZF2 (11.5 g, 20.6 mmol)와 (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-3-yl)boronic acid (7.48 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 347 (12.8 g, 수율 74 %)을 얻었다.Except using 2CZF2 (11.5 g, 20.6 mmol) and (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-3-yl)boronic acid (7.48 g, 20.6 mmol) performed the same process as Synthesis Example 1 to obtain compound 347 (12.8 g, yield 74%).
Mass : [(M+H)+] : 842Mass : [(M+H) + ] : 842
[[ 합성예Synthesis example 133] 화합물133] Compound 349 의349 of 합성 synthesis
2CZO2 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-3-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 349 (11.0 g, 수율 72 %)을 얻었다.Compound 349 ( 11.0 g, yield 72%) was obtained.
Mass : [(M+H)+] : 789Mass : [(M+H) + ] : 789
[[ 합성예Synthesis example 134] 화합물134] Compound 357 의357 합성 synthesis
2CZO2 (11.5 g, 20.6 mmol)와 (9-(naphthalen-2-yl)-9H-carbazol-3-yl)boronic acid (6.95 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 357 (11.4 g, 수율 70 %)을 얻었다.Same process as Synthesis Example 1 except for using 2CZO2 (11.5 g, 20.6 mmol) and (9-(naphthalen-2-yl)-9H-carbazol-3-yl)boronic acid (6.95 g, 20.6 mmol) Compound 357 (11.4 g, yield 70%) was obtained.
Mass : [(M+H)+] : 739Mass : [(M+H) + ] : 739
[[ 합성예Synthesis example 135] 화합물135] Compound 353 의353 합성 synthesis
2CZO3 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-3-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 353 (11.7 g, 수율 77 %)을 얻었다.Compound 353 ( 11.7 g, yield 77%) was obtained.
Mass : [(M+H)+] : 765Mass : [(M+H) + ] : 765
[[ 합성예Synthesis example 136] 화합물136] Compound 360 의360 degrees 합성 synthesis
2CZO3 (11.5 g, 20.6 mmol)와 (9-(phenanthren-2-yl)-9H-carbazol-3-yl)boronic acid (7.98 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 360 (13.0 g, 수율 75 %)을 얻었다.Same process as Synthesis Example 1 except for using 2CZO3 (11.5 g, 20.6 mmol) and (9-(phenanthren-2-yl)-9H-carbazol-3-yl)boronic acid (7.98 g, 20.6 mmol) Compound 360 (13.0 g, yield 75%) was obtained.
Mass : [(M+H)+] : 740Mass : [(M+H) + ] : 740
[[ 합성예Synthesis example 137] 화합물137] Compound 361 의361 of 합성 synthesis
2CZN3 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-3-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 361 (12.7 g, 수율 76 %)을 얻었다.Compound 361 ( 12.7 g, yield 76%) was obtained.
Mass : [(M+H)+] : 815Mass : [(M+H) + ] : 815
[[ 합성예Synthesis example 138] 화합물138] Compound 364 의364 합성 synthesis
2CZN3 (11.5 g, 20.6 mmol)와 (9-([1,1':3',1''-terphenyl]-5'-yl)-9H-carbazol-3-yl)boronic acid (9.05 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 364 (14.7 g, 수율 74 %)을 얻었다.2CZN3 (11.5 g, 20.6 mmol) and (9-([1,1':3',1''-terphenyl]-5'-yl)-9H-carbazol-3-yl)boronic acid (9.05 g, 20.6 Compound 364 (14.7 g, yield 74%) was obtained by performing the same process as Synthesis Example 1 except for using mmol).
Mass : [(M+H)+] : 967Mass : [(M+H) + ] : 967
[[ 합성예Synthesis example 139] 화합물139] Compound 365 의365 of 합성 synthesis
2CZN2 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-3-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 365 (12.7 g, 수율 76 %)을 얻었다.Compound 365 ( 12.7 g, yield 76%) was obtained.
Mass : [(M+H)+] : 815Mass : [(M+H) + ] : 815
[[ 합성예Synthesis example 140] 화합물140] Compound 372 의372 합성 synthesis
2CZN2 (11.5 g, 20.6 mmol)와 (9-(triphenylen-2-yl)-9H-carbazol-3-yl)boronic acid (9.01 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 372 (14.9 g, 수율 75 %)을 얻었다.The same process as Synthesis Example 1 except for using 2CZN2 (11.5 g, 20.6 mmol) and (9-(triphenylen-2-yl)-9H-carbazol-3-yl)boronic acid (9.01 g, 20.6 mmol) Compound 372 (14.9 g, yield 75%) was obtained.
Mass : [(M+H)+] : 965Mass : [(M+H) + ] : 965
[[ 합성예Synthesis example 141] 화합물141] Compound 373 의373 합성 synthesis
2CZS2 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-3-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 373 (11.2 g, 수율 72 %)을 얻었다.Compound 373 ( 11.2 g, yield 72%) was obtained.
Mass : [(M+H)+] : 755Mass : [(M+H) + ] : 755
[[ 합성예Synthesis example 142] 화합물142] Compound 381 의381 합성 synthesis
2CZS2 (11.5 g, 20.6 mmol)와 (9-(naphthalen-1-yl)-9H-carbazol-3-yl)boronic acid (6.95 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 381 (11.6 g, 수율 70 %)을 얻었다.The same process as Synthesis Example 1 except for using 2CZS2 (11.5 g, 20.6 mmol) and (9-(naphthalen-1-yl)-9H-carbazol-3-yl)boronic acid (6.95 g, 20.6 mmol) Compound 381 (11.6 g, yield 70%) was obtained.
Mass : [(M+H)+] : 806Mass : [(M+H) + ] : 806
[[ 합성예Synthesis example 143] 화합물143] Compound 377 의377 합성 synthesis
2CZS3 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-3-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 377 (11.0 g, 수율 71 %)을 얻었다.Compound 377 ( 11.0 g, yield 71%) was obtained.
Mass : [(M+H)+] : 755Mass : [(M+H) + ] : 755
[[ 합성예Synthesis example 144] 화합물144] Compound 379 의379 합성 synthesis
2CZS3 (11.5 g, 20.6 mmol)와 (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-3-yl)boronic acid (7.48 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 379 (12.3 g, 수율 72 %)을 얻었다.Except using 2CZS3 (11.5 g, 20.6 mmol) and (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-3-yl)boronic acid (7.48 g, 20.6 mmol) performed the same process as Synthesis Example 1 to obtain compound 379 (12.3 g, yield 72%).
Mass : [(M+H)+] : 832Mass : [(M+H) + ] : 832
[[ 합성예Synthesis example 145] 화합물145] Compound 385 의385 합성 synthesis
2CZOO2 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-3-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 385 (9.7 g, 수율 80 %)을 얻었다.Compound 385 ( 9.7 g, yield 80%) was obtained.
Mass : [(M+H)+] : 591Mass : [(M+H) + ] : 591
[[ 합성예Synthesis example 146] 화합물146] Compound 386 의386 합성 synthesis
2CZOO2 (11.5 g, 20.6 mmol)와 (9-([1,1'-biphenyl]-3-yl)-9H-carbazol-3-yl)boronic acid (7.48 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 386 (11.3 g, 수율 82 %)을 얻었다.Except using 2CZOO2 (11.5 g, 20.6 mmol) and (9-([1,1'-biphenyl]-3-yl)-9H-carbazol-3-yl)boronic acid (7.48 g, 20.6 mmol) performed the same process as Synthesis Example 1 to obtain compound 386 (11.3 g, yield 82%).
Mass : [(M+H)+] : 667Mass : [(M+H) + ] : 667
[[ 합성예Synthesis example 147] 화합물147] Compound 389 의389 of 합성 synthesis
2CZOO1 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-3-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 389 (9.6 g, 수율 81 %)을 얻었다.Compound 389 ( 9.6 g, yield 81%) was obtained.
Mass : [(M+H)+] : 591Mass : [(M+H) + ] : 591
[[ 합성예Synthesis example 148] 화합물148] Compound 391 의391 of 합성 synthesis
2CZOO1 (11.5 g, 20.6 mmol)와 (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-3-yl)boronic acid (7.48 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 391 (10.8 g, 수율 79 %)을 얻었다.Except using 2CZOO1 (11.5 g, 20.6 mmol) and (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-3-yl)boronic acid (7.48 g, 20.6 mmol) performed the same process as Synthesis Example 1 to obtain compound 391 (10.8 g, yield 79%).
Mass : [(M+H)+] : 667Mass : [(M+H) + ] : 667
[[ 합성예Synthesis example 149] 화합물149] Compound 393 의393 합성 synthesis
2CZF3 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-4-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 393 (11.0 g, 수율 70 %)을 얻었다.Compound 393 ( 11.0 g, yield 70%) was obtained.
Mass : [(M+H)+] : 765Mass : [(M+H) + ] : 765
[[ 합성예Synthesis example 150] 화합물150] Compound 394 의394 합성 synthesis
2CZF3 (11.5 g, 20.6 mmol)와 (9-([1,1'-biphenyl]-3-yl)-9H-carbazol-4-yl)boronic acid (7.48 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 394 (11.9 g, 수율 69 %)을 얻었다.Except using 2CZF3 (11.5 g, 20.6 mmol) and (9-([1,1'-biphenyl]-3-yl)-9H-carbazol-4-yl)boronic acid (7.48 g, 20.6 mmol) performed the same process as Synthesis Example 1 to obtain compound 394 (11.9 g, yield 69%).
Mass : [(M+H)+] : 842Mass : [(M+H) + ] : 842
[[ 합성예Synthesis example 151] 화합물151] Compound 401 의401 of 합성 synthesis
2CZF2 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-4-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 401 (10.7 g, 수율 68 %)을 얻었다.Compound 401 ( 10.7 g, yield 68%) was obtained.
Mass : [(M+H)+] : 765Mass : [(M+H) + ] : 765
[[ 합성예Synthesis example 152] 화합물152] Compound 403 의403 of 합성 synthesis
2CZF2 (11.5 g, 20.6 mmol)와 (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-4-yl)boronic acid (7.48 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 403 (11.9 g, 수율 69 %)을 얻었다.Except using 2CZF2 (11.5 g, 20.6 mmol) and (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-4-yl)boronic acid (7.48 g, 20.6 mmol) performed the same process as Synthesis Example 1 to obtain compound 403 (11.9 g, yield 69%).
Mass : [(M+H)+] : 842Mass : [(M+H) + ] : 842
[[ 합성예Synthesis example 153] 화합물153] Compound 405 의405 of 합성 synthesis
2CZO2 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-4-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 405 (10.8 g, 수율 71 %)을 얻었다.Compound 405 ( 10.8 g, yield 71%) was obtained.
Mass : [(M+H)+] : 789Mass : [(M+H) + ] : 789
[[ 합성예Synthesis example 154] 화합물154] Compound 413 의413 합성 synthesis
2CZO2 (11.5 g, 20.6 mmol)와 (9-(naphthalen-2-yl)-9H-carbazol-4-yl)boronic acid (6.95 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 413 (11.4 g, 수율 70 %)을 얻었다.Same process as Synthesis Example 1 except for using 2CZO2 (11.5 g, 20.6 mmol) and (9-(naphthalen-2-yl)-9H-carbazol-4-yl)boronic acid (6.95 g, 20.6 mmol) Compound 413 (11.4 g, yield 70%) was obtained.
Mass : [(M+H)+] : 739Mass : [(M+H) + ] : 739
[[ 합성예Synthesis example 155] 화합물155] Compound 409 의409 of 합성 synthesis
2CZO3 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-4-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 409 (10.4 g, 수율 68 %)을 얻었다.Compound 409 ( 10.4 g, yield 68%) was obtained.
Mass : [(M+H)+] : 765Mass : [(M+H) + ] : 765
[[ 합성예Synthesis example 156] 화합물156] Compound 416 의416 합성 synthesis
2CZO3 (11.5 g, 20.6 mmol)와 (9-(phenanthren-2-yl)-9H-carbazol-4-yl)boronic acid (7.98 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 416 (11.4 g, 수율 66 %)을 얻었다.Same process as Synthesis Example 1 except for using 2CZO3 (11.5 g, 20.6 mmol) and (9-(phenanthren-2-yl)-9H-carbazol-4-yl)boronic acid (7.98 g, 20.6 mmol) Compound 416 (11.4 g, yield 66%) was obtained.
Mass : [(M+H)+] : 740Mass : [(M+H) + ] : 740
[[ 합성예Synthesis example 157] 화합물157] Compound 417 의417 합성 synthesis
2CZN3 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-4-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 417 (11.4 g, 수율 68 %)을 얻었다.Compound 417 ( 11.4 g, yield 68%) was obtained.
Mass : [(M+H)+] : 815Mass : [(M+H) + ] : 815
[[ 합성예Synthesis example 158] 화합물158] Compound 420 의420 of 합성 synthesis
2CZN3 (11.5 g, 20.6 mmol)와 (9-([1,1':3',1''-terphenyl]-5'-yl)-9H-carbazol-4-yl)boronic acid (9.05 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 420 (12.7 g, 수율 64 %)을 얻었다.2CZN3 (11.5 g, 20.6 mmol) and (9-([1,1':3',1''-terphenyl]-5'-yl)-9H-carbazol-4-yl)boronic acid (9.05 g, 20.6 Compound 420 (12.7 g, yield 64%) was obtained by performing the same process as Synthesis Example 1 except for using mmol).
Mass : [(M+H)+] : 967Mass : [(M+H) + ] : 967
[[ 합성예Synthesis example 159] 화합물159] Compound 421 의421 of 합성 synthesis
2CZN2 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-4-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 421 (11.2 g, 수율 67 %)을 얻었다.Compound 421 ( 11.2 g, yield 67%) was obtained.
Mass : [(M+H)+] : 815Mass : [(M+H) + ] : 815
[[ 합성예Synthesis example 160] 화합물160] Compound 428 의428 합성 synthesis
2CZN2 (11.5 g, 20.6 mmol)와 (9-(triphenylen-2-yl)-9H-carbazol-4-yl)boronic acid (9.01 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 428 (13.1 g, 수율 66 %)을 얻었다.The same process as Synthesis Example 1 except for using 2CZN2 (11.5 g, 20.6 mmol) and (9-(triphenylen-2-yl)-9H-carbazol-4-yl)boronic acid (9.01 g, 20.6 mmol) Compound 428 (13.1 g, yield 66%) was obtained.
Mass : [(M+H)+] : 965Mass : [(M+H) + ] : 965
[[ 합성예Synthesis example 161] 화합물161] Compound 429 의429 of 합성 synthesis
2CZS2 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-4-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 429 (10.7 g, 수율 69 %)을 얻었다.Compound 429 ( 10.7 g, yield 69%) was obtained.
Mass : [(M+H)+] : 755Mass : [(M+H) + ] : 755
[[ 합성예Synthesis example 162] 화합물162] Compound 437 의437 합성 synthesis
2CZS2 (11.5 g, 20.6 mmol)와 (9-(naphthalen-1-yl)-9H-carbazol-4-yl)boronic acid (6.95 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 437 (10.8 g, 수율 65 %)을 얻었다.The same process as Synthesis Example 1 except for using 2CZS2 (11.5 g, 20.6 mmol) and (9-(naphthalen-1-yl)-9H-carbazol-4-yl)boronic acid (6.95 g, 20.6 mmol) Compound 437 (10.8 g, yield 65%) was obtained.
Mass : [(M+H)+] : 806Mass : [(M+H) + ] : 806
[[ 합성예Synthesis example 163] 화합물163] Compound 433 의433 합성 synthesis
2CZS3 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-4-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 433 (9.6 g, 수율 62 %)을 얻었다.Compound 433 ( 9.6 g, yield 62%) was obtained.
Mass : [(M+H)+] : 755Mass : [(M+H) + ] : 755
[[ 합성예Synthesis example 164] 화합물164] Compound 435 의435 합성 synthesis
2CZS3 (11.5 g, 20.6 mmol)와 (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-4-yl)boronic acid (7.48 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 435 (10.6 g, 수율 62 %)을 얻었다.Except using 2CZS3 (11.5 g, 20.6 mmol) and (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-4-yl)boronic acid (7.48 g, 20.6 mmol) Compound 435 (10.6 g, yield 62%) was obtained by performing the same process as Synthesis Example 1.
Mass : [(M+H)+] : 832Mass : [(M+H) + ] : 832
[[ 합성예Synthesis example 165] 화합물165] Compound 441 의441 of 합성 synthesis
2CZOO2 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-4-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 441 (8.6 g, 수율 71 %)을 얻었다.Compound 441 ( 8.6 g, yield 71%) was obtained.
Mass : [(M+H)+] : 591Mass : [(M+H) + ] : 591
[[ 합성예Synthesis example 166] 화합물166] Compound 442 의442 합성 synthesis
2CZOO2 (11.5 g, 20.6 mmol)와 (9-([1,1'-biphenyl]-3-yl)-9H-carbazol-4-yl)boronic acid (7.48 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 442 (9.6 g, 수율 70 %)을 얻었다.Except using 2CZOO2 (11.5 g, 20.6 mmol) and (9-([1,1'-biphenyl]-3-yl)-9H-carbazol-4-yl)boronic acid (7.48 g, 20.6 mmol) performed the same process as Synthesis Example 1 to obtain compound 442 (9.6 g, yield 70%).
Mass : [(M+H)+] : 667Mass : [(M+H) + ] : 667
[[ 합성예Synthesis example 167] 화합물167] Compound 445 의445 합성 synthesis
2CZOO1 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-4-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 445 (8.4 g, 수율 69 %)을 얻었다.Compound 445 ( 8.4 g, yield 69%) was obtained.
Mass : [(M+H)+] : 591Mass : [(M+H) + ] : 591
[[ 합성예Synthesis example 168] 화합물168] Compound 447 의447 합성 synthesis
2CZOO1 (11.5 g, 20.6 mmol)와 (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-4-yl)boronic acid (7.48 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 447 (9.6 g, 수율 70 %)을 얻었다.Except using 2CZOO1 (11.5 g, 20.6 mmol) and (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-4-yl)boronic acid (7.48 g, 20.6 mmol) performed the same process as Synthesis Example 1 to obtain compound 447 (9.6 g, yield 70%).
Mass : [(M+H)+] : 667Mass : [(M+H) + ] : 667
[[ 합성예Synthesis example 169] 화합물169] Compound 449 의449 of 합성 synthesis
1CZF3 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-3-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 449 (9.1 g, 수율 58 %)을 얻었다.Compound 449 ( 9.1 g, yield 58%) was obtained.
Mass : [(M+H)+] : 765Mass : [(M+H) + ] : 765
[[ 합성예Synthesis example 170] 화합물170] Compound 450 의450 of 합성 synthesis
1CZF3 (11.5 g, 20.6 mmol)와 (9-([1,1'-biphenyl]-3-yl)-9H-carbazol-3-yl)boronic acid (7.48 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 450 (9.8 g, 수율 57 %)을 얻었다.Except using 1CZF3 (11.5 g, 20.6 mmol) and (9-([1,1'-biphenyl]-3-yl)-9H-carbazol-3-yl)boronic acid (7.48 g, 20.6 mmol) Compound 450 (9.8 g, yield 57%) was obtained by performing the same process as Synthesis Example 1.
Mass : [(M+H)+] : 842Mass : [(M+H) + ] : 842
[[ 합성예Synthesis example 171] 화합물171] Compound 457 의457 of 합성 synthesis
1CZF2 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-3-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 457 (8.7 g, 수율 55 %)을 얻었다.Compound 457 ( 8.7 g, yield 55%) was obtained.
Mass : [(M+H)+] : 765Mass : [(M+H) + ] : 765
[[ 합성예Synthesis example 172] 화합물172] Compound 459 의459 of 합성 synthesis
1CZF2 (11.5 g, 20.6 mmol)와 (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-3-yl)boronic acid (7.48 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 459 (8.6 g, 수율 50 %)을 얻었다.Except using 1CZF2 (11.5 g, 20.6 mmol) and (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-3-yl)boronic acid (7.48 g, 20.6 mmol) performed the same process as Synthesis Example 1 to obtain compound 459 (8.6 g, yield 50%).
Mass : [(M+H)+] : 842Mass : [(M+H) + ] : 842
[[ 합성예Synthesis example 173] 화합물173] Compound 461 의461 of 합성 synthesis
1CZO2 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-3-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 461 (8.9 g, 수율 59 %)을 얻었다.Compound 461 ( 8.9 g, yield 59%) was obtained.
Mass : [(M+H)+] : 789Mass : [(M+H) + ] : 789
[[ 합성예Synthesis example 174] 화합물174] Compound 469 의469 of 합성 synthesis
1CZO2 (11.5 g, 20.6 mmol)와 (9-(naphthalen-2-yl)-9H-carbazol-3-yl)boronic acid (6.95 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 469 (8.5 g, 수율 52 %)을 얻었다.Same process as Synthesis Example 1 except for using 1CZO2 (11.5 g, 20.6 mmol) and (9-(naphthalen-2-yl)-9H-carbazol-3-yl)boronic acid (6.95 g, 20.6 mmol) Compound 469 (8.5 g, yield 52%) was obtained.
Mass : [(M+H)+] : 739Mass : [(M+H) + ] : 739
[[ 합성예Synthesis example 175] 화합물175] Compound 465 의465 of 합성 synthesis
1CZO3 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-3-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 465 (8.4 g, 수율 55 %)을 얻었다.Compound 465 ( 8.4 g, yield 55%) was obtained.
Mass : [(M+H)+] : 765Mass : [(M+H) + ] : 765
[[ 합성예Synthesis example 176] 화합물176] Compound 472 의472 of 합성 synthesis
1CZO3 (11.5 g, 20.6 mmol)와 (9-(phenanthren-2-yl)-9H-carbazol-3-yl)boronic acid (7.98 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 472 (9.3 g, 수율 54 %)을 얻었다.Same process as Synthesis Example 1 except for using 1CZO3 (11.5 g, 20.6 mmol) and (9-(phenanthren-2-yl)-9H-carbazol-3-yl)boronic acid (7.98 g, 20.6 mmol) Compound 472 (9.3 g, yield 54%) was obtained.
Mass : [(M+H)+] : 740Mass : [(M+H) + ] : 740
[[ 합성예Synthesis example 177] 화합물177] Compound 473 의473 합성 synthesis
1CZN3 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-3-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 473 (9.7 g, 수율 58 %)을 얻었다.Compound 473 ( 9.7 g, yield 58%) was obtained.
Mass : [(M+H)+] : 815Mass : [(M+H) + ] : 815
[[ 합성예Synthesis example 178] 화합물178] Compound 476 의476 합성 synthesis
1CZN3 (11.5 g, 20.6 mmol)와 (9-([1,1':3',1''-terphenyl]-5'-yl)-9H-carbazol-3-yl)boronic acid (9.05 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 476 (10.5 g, 수율 53 %)을 얻었다.1CZN3 (11.5 g, 20.6 mmol) and (9-([1,1':3',1''-terphenyl]-5'-yl)-9H-carbazol-3-yl)boronic acid (9.05 g, 20.6 Compound 476 (10.5 g, yield 53%) was obtained by performing the same process as Synthesis Example 1 except for using mmol).
Mass : [(M+H)+] : 967Mass : [(M+H) + ] : 967
[[ 합성예Synthesis example 179] 화합물179] Compound 477 의477 합성 synthesis
1CZN2 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-3-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 477 (9.2 g, 수율 55 %)을 얻었다.Compound 477 ( 9.2 g, yield 55%) was obtained.
Mass : [(M+H)+] : 815Mass : [(M+H) + ] : 815
[[ 합성예Synthesis example 180] 화합물180] Compound 484 의484 합성 synthesis
1CZN2 (11.5 g, 20.6 mmol)와 (9-(triphenylen-2-yl)-9H-carbazol-3-yl)boronic acid (9.01 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 484 (11.3 g, 수율 57 %)을 얻었다.Same process as Synthesis Example 1 except for using 1CZN2 (11.5 g, 20.6 mmol) and (9-(triphenylen-2-yl)-9H-carbazol-3-yl)boronic acid (9.01 g, 20.6 mmol) Compound 484 (11.3 g, yield 57%) was obtained.
Mass : [(M+H)+] : 965Mass : [(M+H) + ] : 965
[[ 합성예Synthesis example 181] 화합물181] Compound 485 의485 of 합성 synthesis
1CZS2 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-3-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 485 (9.2 g, 수율 59 %)을 얻었다.Compound 485 ( 9.2 g, yield 59%) was obtained.
Mass : [(M+H)+] : 755Mass : [(M+H) + ] : 755
[[ 합성예Synthesis example 182] 화합물182] Compound 493 의493 of 합성 synthesis
1CZS2 (11.5 g, 20.6 mmol)와 (9-(naphthalen-1-yl)-9H-carbazol-3-yl)boronic acid (6.95 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 493 (9.5 g, 수율 57 %)을 얻었다.Same process as Synthesis Example 1 except for using 1CZS2 (11.5 g, 20.6 mmol) and (9-(naphthalen-1-yl)-9H-carbazol-3-yl)boronic acid (6.95 g, 20.6 mmol) Compound 493 (9.5 g, yield 57%) was obtained.
Mass : [(M+H)+] : 806Mass : [(M+H) + ] : 806
[[ 합성예Synthesis example 183] 화합물183] Compound 489 의489 of 합성 synthesis
1CZS3 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-3-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 489 (8.7 g, 수율 56 %)을 얻었다.Compound 489 ( 8.7 g, yield 56%) was obtained.
Mass : [(M+H)+] : 755Mass : [(M+H) + ] : 755
[[ 합성예Synthesis example 184] 화합물184] Compound 491 의491 of 합성 synthesis
1CZS3 (11.5 g, 20.6 mmol)와 (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-3-yl)boronic acid (7.48 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 491 (9.4 g, 수율 55 %)을 얻었다.Except using 1CZS3 (11.5 g, 20.6 mmol) and (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-3-yl)boronic acid (7.48 g, 20.6 mmol) performed the same process as Synthesis Example 1 to obtain compound 491 (9.4 g, yield 55%).
Mass : [(M+H)+] : 832Mass : [(M+H) + ] : 832
[[ 합성예Synthesis example 185] 화합물185] Compound 497 의497 of 합성 synthesis
1CZOO2 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-3-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 497 (7.2 g, 수율 59 %)을 얻었다.Compound 497 ( 7.2 g, yield 59%) was obtained.
Mass : [(M+H)+] : 591Mass : [(M+H) + ] : 591
[[ 합성예Synthesis example 186] 화합물186] Compound 498 의498 of 합성 synthesis
1CZOO2 (11.5 g, 20.6 mmol)와 (9-([1,1'-biphenyl]-3-yl)-9H-carbazol-3-yl)boronic acid (7.48 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 498 (8.2 g, 수율 60 %)을 얻었다.Except using 1CZOO2 (11.5 g, 20.6 mmol) and (9-([1,1'-biphenyl]-3-yl)-9H-carbazol-3-yl)boronic acid (7.48 g, 20.6 mmol) performed the same process as Synthesis Example 1 to obtain compound 498 (8.2 g, yield 60%).
Mass : [(M+H)+] : 667Mass : [(M+H) + ] : 667
[[ 합성예Synthesis example 187] 화합물187] Compound 501 의501 of 합성 synthesis
1CZOO1 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-3-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 501 (6.9 g, 수율 57 %)을 얻었다.Compound 501 ( 6.9 g, yield 57%) was obtained.
Mass : [(M+H)+] : 591Mass : [(M+H) + ] : 591
[[ 합성예Synthesis example 188] 화합물188] Compound 503 의503 of 합성 synthesis
1CZOO1 (11.5 g, 20.6 mmol)와 (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-3-yl)boronic acid (7.48 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 503 (7.4 g, 수율 54 %)을 얻었다.Except using 1CZOO1 (11.5 g, 20.6 mmol) and (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-3-yl)boronic acid (7.48 g, 20.6 mmol) performed the same process as Synthesis Example 1 to obtain compound 503 (7.4 g, yield 54%).
Mass : [(M+H)+] : 667Mass : [(M+H) + ] : 667
[[ 합성예Synthesis example 189] 화합물189] Compound 505 의505 of 합성 synthesis
4CZF3 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-3-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 505 (9.8 g, 수율 62 %)을 얻었다.Compound 505 ( 9.8 g, yield 62%) was obtained.
Mass : [(M+H)+] : 765Mass : [(M+H) + ] : 765
[[ 합성예Synthesis example 190] 화합물190] Compound 506 의506 of 합성 synthesis
4CZF3 (11.5 g, 20.6 mmol)와 (9-([1,1'-biphenyl]-3-yl)-9H-carbazol-3-yl)boronic acid (7.48 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 506 (10.4 g, 수율 60 %)을 얻었다.Except using 4CZF3 (11.5 g, 20.6 mmol) and (9-([1,1'-biphenyl]-3-yl)-9H-carbazol-3-yl)boronic acid (7.48 g, 20.6 mmol) Compound 506 (10.4 g, yield 60%) was obtained by performing the same process as Synthesis Example 1.
Mass : [(M+H)+] : 842Mass : [(M+H) + ] : 842
[[ 합성예Synthesis example 191] 화합물191] Compound 513 의513 합성 synthesis
4CZF2 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-3-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 513 (9.9 g, 수율 63 %)을 얻었다.Compound 513 ( 9.9 g, yield 63%) was obtained.
Mass : [(M+H)+] : 765Mass : [(M+H) + ] : 765
[[ 합성예Synthesis example 192] 화합물192] Compound 515 의515 of 합성 synthesis
4CZF2 (11.5 g, 20.6 mmol)와 (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-3-yl)boronic acid (7.48 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 515 (10.6 g, 수율 61 %)을 얻었다.Except using 4CZF2 (11.5 g, 20.6 mmol) and (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-3-yl)boronic acid (7.48 g, 20.6 mmol) Compound 515 (10.6 g, yield 61%) was obtained by performing the same process as Synthesis Example 1.
Mass : [(M+H)+] : 842Mass : [(M+H) + ] : 842
[[ 합성예Synthesis example 193] 화합물193] Compound 517 의517 of 합성 synthesis
4CZO2 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-3-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 517 (9.1 g, 수율 60 %)을 얻었다.Compound 517 ( 9.1 g, yield 60%) was obtained.
Mass : [(M+H)+] : 789Mass : [(M+H) + ] : 789
[[ 합성예Synthesis example 194] 화합물194] Compound 525 의525 of 합성 synthesis
4CZO2 (11.5 g, 20.6 mmol)와 (9-(naphthalen-2-yl)-9H-carbazol-3-yl)boronic acid (6.95 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 525 (10.4 g, 수율 64 %)을 얻었다.Same process as Synthesis Example 1 except for using 4CZO2 (11.5 g, 20.6 mmol) and (9-(naphthalen-2-yl)-9H-carbazol-3-yl)boronic acid (6.95 g, 20.6 mmol) Compound 525 (10.4 g, yield 64%) was obtained.
Mass : [(M+H)+] : 739Mass : [(M+H) + ] : 739
[[ 합성예Synthesis example 195] 화합물195] Compound 521 의521 of 합성 synthesis
4CZO3 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-3-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 521 (9.4 g, 수율 62 %)을 얻었다.Compound 521 ( 9.4 g, yield 62%) was obtained.
Mass : [(M+H)+] : 765Mass : [(M+H) + ] : 765
[[ 합성예Synthesis example 196] 화합물196] Compound 528 의528 합성 synthesis
4CZO3 (11.5 g, 20.6 mmol)와 (9-(phenanthren-2-yl)-9H-carbazol-3-yl)boronic acid (7.98 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 528 (10.4 g, 수율 60 %)을 얻었다.Same process as Synthesis Example 1 except for using 4CZO3 (11.5 g, 20.6 mmol) and (9-(phenanthren-2-yl)-9H-carbazol-3-yl)boronic acid (7.98 g, 20.6 mmol) Compound 528 (10.4 g, yield 60%) was obtained.
Mass : [(M+H)+] : 740Mass : [(M+H) + ] : 740
[[ 합성예Synthesis example 197] 화합물197] Compound 529 의529 of 합성 synthesis
4CZN3 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-3-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 529 (11.1 g, 수율 66 %)을 얻었다.Compound 529 ( 11.1 g, yield 66%) was obtained.
Mass : [(M+H)+] : 815Mass : [(M+H) + ] : 815
[[ 합성예Synthesis example 198] 화합물198] Compound 532 의532 합성 synthesis
4CZN3 (11.5 g, 20.6 mmol)와 (9-([1,1':3',1''-terphenyl]-5'-yl)-9H-carbazol-3-yl)boronic acid (9.05 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 532 (12.3 g, 수율 62 %)을 얻었다.4CZN3 (11.5 g, 20.6 mmol) and (9-([1,1':3',1''-terphenyl]-5'-yl)-9H-carbazol-3-yl)boronic acid (9.05 g, 20.6 Compound 532 (12.3 g, yield 62%) was obtained by performing the same process as Synthesis Example 1 except for using mmol).
Mass : [(M+H)+] : 967Mass : [(M+H) + ] : 967
[[ 합성예Synthesis example 199] 화합물199] Compound 533 의533 합성 synthesis
4CZN2 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-3-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 533 (10.1 g, 수율 60 %)을 얻었다.Compound 533 ( 10.1 g, yield 60%) was obtained.
Mass : [(M+H)+] : 815Mass : [(M+H) + ] : 815
[[ 합성예Synthesis example 200] 화합물200] Compound 540 의540 of 합성 synthesis
4CZN2 (11.5 g, 20.6 mmol)와 (9-(triphenylen-2-yl)-9H-carbazol-3-yl)boronic acid (9.01 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 540 (12.7 g, 수율 64 %)을 얻었다.Same process as Synthesis Example 1 except for using 4CZN2 (11.5 g, 20.6 mmol) and (9-(triphenylen-2-yl)-9H-carbazol-3-yl)boronic acid (9.01 g, 20.6 mmol) Compound 540 (12.7 g, yield 64%) was obtained.
Mass : [(M+H)+] : 965Mass : [(M+H) + ] : 965
[[ 합성예Synthesis example 201] 화합물201] Compound 541 의541 합성 synthesis
4CZS2 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-3-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 541 (9.3 g, 수율 60 %)을 얻었다.Compound 541 ( 9.3 g, yield 60%) was obtained.
Mass : [(M+H)+] : 755Mass : [(M+H) + ] : 755
[[ 합성예Synthesis example 202] 화합물202] Compound 549 의549 of 합성 synthesis
4CZS2 (11.5 g, 20.6 mmol)와 (9-(naphthalen-1-yl)-9H-carbazol-3-yl)boronic acid (6.95 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 549 (10.3 g, 수율 62 %)을 얻었다.Same process as Synthesis Example 1 except for using 4CZS2 (11.5 g, 20.6 mmol) and (9-(naphthalen-1-yl)-9H-carbazol-3-yl)boronic acid (6.95 g, 20.6 mmol) Compound 549 (10.3 g, yield 62%) was obtained.
Mass : [(M+H)+] : 806Mass : [(M+H) + ] : 806
[[ 합성예Synthesis example 203] 화합물203] Compound 545 의545 of 합성 synthesis
4CZS3 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-3-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 545 (9.9 g, 수율 64 %)을 얻었다.Compound 545 ( 9.9 g, yield 64%) was obtained.
Mass : [(M+H)+] : 755Mass : [(M+H) + ] : 755
[[ 합성예Synthesis example 204] 화합물204] Compound 547 의547 합성 synthesis
4CZS3 (11.5 g, 20.6 mmol)와 (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-3-yl)boronic acid (7.48 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 547 (9.9 g, 수율 58 %)을 얻었다.Except using 4CZS3 (11.5 g, 20.6 mmol) and (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-3-yl)boronic acid (7.48 g, 20.6 mmol) performed the same process as Synthesis Example 1 to obtain compound 547 (9.9 g, yield 58%).
Mass : [(M+H)+] : 832Mass : [(M+H) + ] : 832
[[ 합성예Synthesis example 205] 화합물205] Compound 553 의553 합성 synthesis
4CZOO2 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-3-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 553 (7.5 g, 수율 62 %)을 얻었다.Compound 553 ( 7.5 g, yield 62%) was obtained.
Mass : [(M+H)+] : 591Mass : [(M+H) + ] : 591
[[ 합성예Synthesis example 206] 화합물206] Compound 554 의554 of 합성 synthesis
4CZOO2 (11.5 g, 20.6 mmol)와 (9-([1,1'-biphenyl]-3-yl)-9H-carbazol-3-yl)boronic acid (7.48 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 554 (8.3 g, 수율 60 %)을 얻었다.Except using 4CZOO2 (11.5 g, 20.6 mmol) and (9-([1,1'-biphenyl]-3-yl)-9H-carbazol-3-yl)boronic acid (7.48 g, 20.6 mmol) performed the same process as Synthesis Example 1 to obtain compound 554 (8.3 g, yield 60%).
Mass : [(M+H)+] : 667Mass : [(M+H) + ] : 667
[[ 합성예Synthesis example 207] 화합물207] Compound 557 의557 of 합성 synthesis
4CZOO1 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-3-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 557 (7.5 g, 수율 62 %)을 얻었다.Compound 557 ( 7.5 g, yield 62%) was obtained.
Mass : [(M+H)+] : 591Mass : [(M+H) + ] : 591
[[ 합성예Synthesis example 208] 화합물208] Compound 559 의559 of 합성 synthesis
4CZOO1 (11.5 g, 20.6 mmol)와 (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-3-yl)boronic acid (7.48 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 559 (8.4 g, 수율 61 %)을 얻었다.Except using 4CZOO1 (11.5 g, 20.6 mmol) and (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-3-yl)boronic acid (7.48 g, 20.6 mmol) performed the same process as Synthesis Example 1 to obtain compound 559 (8.4 g, yield 61%).
Mass : [(M+H)+] : 667Mass : [(M+H) + ] : 667
[[ 합성예Synthesis example 209] 화합물209] Compound 561 의561 of 합성 synthesis
1CZF3 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-2-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 561 (8.7 g, 수율 55 %)을 얻었다.Compound 561 ( 8.7 g, yield 55%) was obtained.
Mass : [(M+H)+] : 765Mass : [(M+H) + ] : 765
[[ 합성예Synthesis example 210] 화합물210] Compound 562 의562 of 합성 synthesis
1CZF3 (11.5 g, 20.6 mmol)와 (9-([1,1'-biphenyl]-3-yl)-9H-carbazol-2-yl)boronic acid (7.48 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 562 (9.0 g, 수율 52 %)을 얻었다.Except using 1CZF3 (11.5 g, 20.6 mmol) and (9-([1,1'-biphenyl]-3-yl)-9H-carbazol-2-yl)boronic acid (7.48 g, 20.6 mmol) performed the same process as Synthesis Example 1 to obtain compound 562 (9.0 g, yield 52%).
Mass : [(M+H)+] : 842Mass : [(M+H) + ] : 842
[[ 합성예Synthesis example 211] 화합물211] Compound 569 의569 of 합성 synthesis
1CZF2 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-2-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 569 (8.5 g, 수율 54 %)을 얻었다.Compound 569 ( 8.5 g, yield 54%) was obtained.
Mass : [(M+H)+] : 765Mass : [(M+H) + ] : 765
[[ 합성예Synthesis example 212] 화합물212] Compound 571 의571 of 합성 synthesis
1CZF2 (11.5 g, 20.6 mmol)와 (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-2-yl)boronic acid (7.48 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 571 (8.6 g, 수율 50 %)을 얻었다.Except using 1CZF2 (11.5 g, 20.6 mmol) and (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-2-yl)boronic acid (7.48 g, 20.6 mmol) performed the same process as Synthesis Example 1 to obtain compound 571 (8.6 g, yield 50%).
Mass : [(M+H)+] : 842Mass : [(M+H) + ] : 842
[[ 합성예Synthesis example 213] 화합물213] Compound 573 의573 합성 synthesis
1CZO2 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-2-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 573 (7.8 g, 수율 51 %)을 얻었다.Compound 573 ( 7.8 g, yield 51%) was obtained.
Mass : [(M+H)+] : 789Mass : [(M+H) + ] : 789
[[ 합성예Synthesis example 214] 화합물214] Compound 581 의581 of 합성 synthesis
1CZO2 (11.5 g, 20.6 mmol)와 (9-(naphthalen-2-yl)-9H-carbazol-2-yl)boronic acid (6.95 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 581 (8.2 g, 수율 50 %)을 얻었다.Same process as Synthesis Example 1 except for using 1CZO2 (11.5 g, 20.6 mmol) and (9-(naphthalen-2-yl)-9H-carbazol-2-yl)boronic acid (6.95 g, 20.6 mmol) Compound 581 (8.2 g, yield 50%) was obtained.
Mass : [(M+H)+] : 739Mass : [(M+H) + ] : 739
[[ 합성예Synthesis example 215] 화합물215] Compound 577 의577 합성 synthesis
1CZO3 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-2-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 585 (7.9 g, 수율 52 %)을 얻었다.Compound 585 ( 7.9 g, yield 52%) was obtained.
Mass : [(M+H)+] : 765Mass : [(M+H) + ] : 765
[[ 합성예Synthesis example 216] 화합물216] Compound 584 의584 합성 synthesis
1CZO3 (11.5 g, 20.6 mmol)와 (9-(phenanthren-2-yl)-9H-carbazol-2-yl)boronic acid (7.98 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 584 (9.2 g, 수율 53 %)을 얻었다.Same process as Synthesis Example 1 except for using 1CZO3 (11.5 g, 20.6 mmol) and (9-(phenanthren-2-yl)-9H-carbazol-2-yl)boronic acid (7.98 g, 20.6 mmol) Compound 584 (9.2 g, yield 53%) was obtained.
Mass : [(M+H)+] : 740Mass : [(M+H) + ] : 740
[[ 합성예Synthesis example 217] 화합물217] Compound 585 의585 of 합성 synthesis
1CZN3 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-2-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 585 (9.2 g, 수율 55 %)을 얻었다.Compound 585 ( 9.2 g, yield 55%) was obtained.
Mass : [(M+H)+] : 815Mass : [(M+H) + ] : 815
[[ 합성예Synthesis example 218] 화합물218] Compound 588 의588 합성 synthesis
1CZN3 (11.5 g, 20.6 mmol)와 (9-([1,1':3',1''-terphenyl]-5'-yl)-9H-carbazol-2-yl)boronic acid (9.05 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 588 (10.6 g, 수율 53 %)을 얻었다.1CZN3 (11.5 g, 20.6 mmol) and (9-([1,1':3',1''-terphenyl]-5'-yl)-9H-carbazol-2-yl)boronic acid (9.05 g, 20.6 Compound 588 (10.6 g, yield 53%) was obtained by performing the same process as Synthesis Example 1 except for using mmol).
Mass : [(M+H)+] : 967Mass : [(M+H) + ] : 967
[[ 합성예Synthesis example 219] 화합물219] Compound 589 의589 of 합성 synthesis
1CZN2 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-2-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 589 (9.1 g, 수율 54 %)을 얻었다.Compound 589 ( 9.1 g, yield 54%) was obtained.
Mass : [(M+H)+] : 815Mass : [(M+H) + ] : 815
[[ 합성예Synthesis example 220] 화합물220] Compound 596 의596 of 합성 synthesis
1CZN2 (11.5 g, 20.6 mmol)와 (9-(triphenylen-2-yl)-9H-carbazol-2-yl)boronic acid (9.01 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 596 (10.3 g, 수율 52 %)을 얻었다.Same process as Synthesis Example 1 except for using 1CZN2 (11.5 g, 20.6 mmol) and (9-(triphenylen-2-yl)-9H-carbazol-2-yl)boronic acid (9.01 g, 20.6 mmol) Compound 596 (10.3 g, yield 52%) was obtained.
Mass : [(M+H)+] : 965Mass : [(M+H) + ] : 965
[[ 합성예Synthesis example 221] 화합물221] Compound 597 의597 of 합성 synthesis
Mass : [(M+H)+] : 755Mass : [(M+H) + ] : 755
[[ 합성예Synthesis example 222] 화합물222] Compound 605 의605 of 합성 synthesis
1CZS2 (11.5 g, 20.6 mmol)와 (9-(naphthalen-1-yl)-9H-carbazol-2-yl)boronic acid (6.95 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 605 (8.6 g, 수율 52 %)을 얻었다.Same process as Synthesis Example 1 except for using 1CZS2 (11.5 g, 20.6 mmol) and (9-(naphthalen-1-yl)-9H-carbazol-2-yl)boronic acid (6.95 g, 20.6 mmol) Compound 605 (8.6 g, yield 52%) was obtained.
Mass : [(M+H)+] : 806Mass : [(M+H) + ] : 806
[[ 합성예Synthesis example 223] 화합물223] Compound 601 의601 of 합성 synthesis
1CZS3 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-2-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 601 (8.2 g, 수율 53 %)을 얻었다.Compound 601 ( 8.2 g, yield 53%) was obtained.
Mass : [(M+H)+] : 755Mass : [(M+H) + ] : 755
[[ 합성예Synthesis example 224] 화합물224] Compound 603 의603 of 합성 synthesis
1CZS3 (11.5 g, 20.6 mmol)와 (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-2-yl)boronic acid (7.48 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 603 (8.6 g, 수율 50 %)을 얻었다.Except using 1CZS3 (11.5 g, 20.6 mmol) and (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-2-yl)boronic acid (7.48 g, 20.6 mmol) performed the same process as Synthesis Example 1 to obtain compound 603 (8.6 g, yield 50%).
Mass : [(M+H)+] : 832Mass : [(M+H) + ] : 832
[[ 합성예Synthesis example 225] 화합물225] Compound 609 의609 of 합성 synthesis
1CZOO2 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-2-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 609 (6.9 g, 수율 57 %)을 얻었다.Compound 609 ( 6.9 g, yield 57%) was obtained.
Mass : [(M+H)+] : 591Mass : [(M+H) + ] : 591
[[ 합성예Synthesis example 226] 화합물226] Compound 610 의610 of 합성 synthesis
1CZOO2 (11.5 g, 20.6 mmol)와 (9-([1,1'-biphenyl]-3-yl)-9H-carbazol-2-yl)boronic acid (7.48 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 610 (7.3 g, 수율 53 %)을 얻었다.Except using 1CZOO2 (11.5 g, 20.6 mmol) and (9-([1,1'-biphenyl]-3-yl)-9H-carbazol-2-yl)boronic acid (7.48 g, 20.6 mmol) performed the same process as Synthesis Example 1 to obtain compound 610 (7.3 g, yield 53%).
Mass : [(M+H)+] : 667Mass : [(M+H) + ] : 667
[[ 합성예Synthesis example 227] 화합물227] Compound 613 의613 합성 synthesis
1CZOO1 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-2-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 613 (6.8 g, 수율 56 %)을 얻었다.Compound 613 ( 6.8 g, yield 56%) was obtained.
Mass : [(M+H)+] : 591Mass : [(M+H) + ] : 591
[[ 합성예Synthesis example 228] 화합물228] Compound 615 의615 합성 synthesis
1CZOO1 (11.5 g, 20.6 mmol)와 (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-2-yl)boronic acid (7.48 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 615 (7.4 g, 수율 54 %)을 얻었다.Except using 1CZOO1 (11.5 g, 20.6 mmol) and (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-2-yl)boronic acid (7.48 g, 20.6 mmol) performed the same process as Synthesis Example 1 to obtain compound 615 (7.4 g, yield 54%).
Mass : [(M+H)+] : 667Mass : [(M+H) + ] : 667
[[ 합성예Synthesis example 229] 화합물229] Compound 617 의617 합성 synthesis
4CZF3 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-2-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 617 (8.2 g, 수율 52 %)을 얻었다.Compound 617 ( 8.2 g, yield 52%) was obtained.
Mass : [(M+H)+] : 765Mass : [(M+H) + ] : 765
[[ 합성예Synthesis example 230] 화합물230] Compound 618 의618 합성 synthesis
4CZF3 (11.5 g, 20.6 mmol)와 (9-([1,1'-biphenyl]-3-yl)-9H-carbazol-2-yl)boronic acid (7.48 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 618 (9.2 g, 수율 53 %)을 얻었다.Except using 4CZF3 (11.5 g, 20.6 mmol) and (9-([1,1'-biphenyl]-3-yl)-9H-carbazol-2-yl)boronic acid (7.48 g, 20.6 mmol) performed the same process as Synthesis Example 1 to obtain compound 618 (9.2 g, yield 53%).
Mass : [(M+H)+] : 842Mass : [(M+H) + ] : 842
[[ 합성예Synthesis example 231] 화합물231] Compound 625 의625 합성 synthesis
4CZF2 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-2-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 625 (8.4 g, 수율 53 %)을 얻었다.Compound 625 ( 8.4 g, yield 53%) was obtained.
Mass : [(M+H)+] : 765Mass : [(M+H) + ] : 765
[[ 합성예Synthesis example 232] 화합물232] Compound 627 의627 합성 synthesis
4CZF2 (11.5 g, 20.6 mmol)와 (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-2-yl)boronic acid (7.48 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 627 (8.8 g, 수율 51 %)을 얻었다.Except using 4CZF2 (11.5 g, 20.6 mmol) and (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-2-yl)boronic acid (7.48 g, 20.6 mmol) performed the same process as Synthesis Example 1 to obtain compound 627 (8.8 g, yield 51%).
Mass : [(M+H)+] : 842Mass : [(M+H) + ] : 842
[[ 합성예Synthesis example 233] 화합물233] Compound 629 의629 of 합성 synthesis
4CZO2 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-2-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 629 (7.9 g, 수율 52 %)을 얻었다.Compound 629 ( 7.9 g, yield 52%) was obtained.
Mass : [(M+H)+] : 789Mass : [(M+H) + ] : 789
[[ 합성예Synthesis example 234] 화합물234] Compound 637 의637 합성 synthesis
4CZO2 (11.5 g, 20.6 mmol)와 (9-(naphthalen-2-yl)-9H-carbazol-2-yl)boronic acid (6.95 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 637 (8.1 g, 수율 50 %)을 얻었다.Same process as Synthesis Example 1 except for using 4CZO2 (11.5 g, 20.6 mmol) and (9-(naphthalen-2-yl)-9H-carbazol-2-yl)boronic acid (6.95 g, 20.6 mmol) Compound 637 (8.1 g, yield 50%) was obtained.
Mass : [(M+H)+] : 739Mass : [(M+H) + ] : 739
[[ 합성예Synthesis example 235] 화합물235] Compound 633 의633 합성 synthesis
4CZO3 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-2-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 633 (8.1 g, 수율 53 %)을 얻었다.Compound 633 ( 8.1 g, yield 53%) was obtained.
Mass : [(M+H)+] : 765Mass : [(M+H) + ] : 765
[[ 합성예Synthesis example 236] 화합물236] Compound 640 의640 of 합성 synthesis
4CZO3 (11.5 g, 20.6 mmol)와 (9-(phenanthren-2-yl)-9H-carbazol-2-yl)boronic acid (7.98 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 640 (8.6 g, 수율 50 %)을 얻었다.Same process as Synthesis Example 1 except for using 4CZO3 (11.5 g, 20.6 mmol) and (9-(phenanthren-2-yl)-9H-carbazol-2-yl)boronic acid (7.98 g, 20.6 mmol) Compound 640 (8.6 g, yield 50%) was obtained.
Mass : [(M+H)+] : 740Mass : [(M+H) + ] : 740
[[ 합성예Synthesis example 237] 화합물237] Compound 641 의641 of 합성 synthesis
4CZN3 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-2-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 641 (8.5 g, 수율 51 %)을 얻었다.Compound 641 ( 8.5 g, yield 51%) was obtained.
Mass : [(M+H)+] : 815Mass : [(M+H) + ] : 815
[[ 합성예Synthesis example 238] 화합물238] Compound 644 의644 합성 synthesis
4CZN3 (11.5 g, 20.6 mmol)와 (9-([1,1':3',1''-terphenyl]-5'-yl)-9H-carbazol-2-yl)boronic acid (9.05 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 644 (9.9 g, 수율 50 %)을 얻었다.4CZN3 (11.5 g, 20.6 mmol) and (9-([1,1':3',1''-terphenyl]-5'-yl)-9H-carbazol-2-yl)boronic acid (9.05 g, 20.6 Compound 644 (9.9 g, yield 50%) was obtained by performing the same process as Synthesis Example 1 except for using mmol).
Mass : [(M+H)+] : 967Mass : [(M+H) + ] : 967
[[ 합성예Synthesis example 239] 화합물239] Compound 645 의645 합성 synthesis
4CZN2 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-2-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 645 (8.7 g, 수율 52 %)을 얻었다.Compound 645 ( 8.7 g, yield 52%) was obtained.
Mass : [(M+H)+] : 815Mass : [(M+H) + ] : 815
[[ 합성예Synthesis example 240] 화합물240] Compound 652 의652 of 합성 synthesis
4CZN2 (11.5 g, 20.6 mmol)와 (9-(triphenylen-2-yl)-9H-carbazol-2-yl)boronic acid (9.01 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 652 (9.7 g, 수율 49 %)을 얻었다.Same process as Synthesis Example 1 except for using 4CZN2 (11.5 g, 20.6 mmol) and (9-(triphenylen-2-yl)-9H-carbazol-2-yl)boronic acid (9.01 g, 20.6 mmol) Compound 652 (9.7 g, yield 49%) was obtained.
Mass : [(M+H)+] : 965Mass : [(M+H) + ] : 965
[[ 합성예Synthesis example 241] 화합물241] Compound 653 의653 합성 synthesis
4CZS2 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-2-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 653 (8.1 g, 수율 52 %)을 얻었다.Compound 653 ( 8.1 g, yield 52%) was obtained.
Mass : [(M+H)+] : 755Mass : [(M+H) + ] : 755
[[ 합성예Synthesis example 242] 화합물242] Compound 661 의661 of 합성 synthesis
4CZS2 (11.5 g, 20.6 mmol)와 (9-(naphthalen-1-yl)-9H-carbazol-2-yl)boronic acid (6.95 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 661 (8.3 g, 수율 50 %)을 얻었다.Same procedure as Synthesis Example 1 except for using 4CZS2 (11.5 g, 20.6 mmol) and (9-(naphthalen-1-yl)-9H-carbazol-2-yl)boronic acid (6.95 g, 20.6 mmol) Compound 661 (8.3 g, yield 50%) was obtained.
Mass : [(M+H)+] : 806Mass : [(M+H) + ] : 806
[[ 합성예Synthesis example 243] 화합물243] Compound 657 의657 합성 synthesis
4CZS3 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-2-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 657 (7.9 g, 수율 51 %)을 얻었다.Compound 657 ( 7.9 g, yield 51%) was obtained.
Mass : [(M+H)+] : 755Mass : [(M+H) + ] : 755
[[ 합성예Synthesis example 244] 화합물244] Compound 659 의659 of 합성 synthesis
4CZS3 (11.5 g, 20.6 mmol)와 (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-2-yl)boronic acid (7.48 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 659 (8.9 g, 수율 52 %)을 얻었다.Except using 4CZS3 (11.5 g, 20.6 mmol) and (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-2-yl)boronic acid (7.48 g, 20.6 mmol) performed the same process as Synthesis Example 1 to obtain compound 659 (8.9 g, yield 52%).
Mass : [(M+H)+] : 832Mass : [(M+H) + ] : 832
[[ 합성예Synthesis example 245] 화합물245] Compound 665 의665 of 합성 synthesis
4CZOO2 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-2-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 665 (6.5 g, 수율 53 %)을 얻었다.Compound 665 ( 6.5 g, yield 53%) was obtained.
Mass : [(M+H)+] : 591Mass : [(M+H) + ] : 591
[[ 합성예Synthesis example 246] 화합물246] Compound 666 의666 합성 synthesis
4CZOO2 (11.5 g, 20.6 mmol)와 (9-([1,1'-biphenyl]-3-yl)-9H-carbazol-2-yl)boronic acid (7.48 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 666 (7.1 g, 수율 52 %)을 얻었다.Except using 4CZOO2 (11.5 g, 20.6 mmol) and (9-([1,1'-biphenyl]-3-yl)-9H-carbazol-2-yl)boronic acid (7.48 g, 20.6 mmol) performed the same process as Synthesis Example 1 to obtain compound 666 (7.1 g, yield 52%).
Mass : [(M+H)+] : 667Mass : [(M+H) + ] : 667
[[ 합성예Synthesis example 247] 화합물247] Compound 669 의669 of 합성 synthesis
4CZOO1 (11.5 g, 20.6 mmol)와 (9-phenyl-9H-carbazol-2-yl)boronic acid (5.9 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 669 (6.6 g, 수율 54 %)을 얻었다.Compound 669 ( 6.6 g, yield 54%) was obtained.
Mass : [(M+H)+] : 591Mass : [(M+H) + ] : 591
[[ 합성예Synthesis example 248] 화합물248] Compound 671 의671 of 합성 synthesis
4CZOO1 (11.5 g, 20.6 mmol)와 (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-2-yl)boronic acid (7.48 g, 20.6 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 671 (7.4 g, 수율 50 %)을 얻었다.Except using 4CZOO1 (11.5 g, 20.6 mmol) and (9-([1,1'-biphenyl]-4-yl)-9H-carbazol-2-yl)boronic acid (7.48 g, 20.6 mmol) performed the same process as Synthesis Example 1 to obtain compound 671 (7.4 g, yield 50%).
Mass : [(M+H)+] : 667Mass : [(M+H) + ] : 667
[[ 실시예Example 1 내지 248] 녹색 유기 1 to 248] green organic 전계electric field 발광 소자의 제작 Fabrication of light emitting devices
합성예에서 합성한 화합물(하기 표 2 참조)을 통상적으로 알려진 방법으로 고순도 승화정제를 한 후 아래의 과정에 따라 녹색 유기 전계 발광 소자를 제작하였다.The compound synthesized in the synthesis example (see Table 2 below) was purified to high purity by sublimation using a commonly known method, and then a green organic electroluminescent device was manufactured according to the process below.
먼저, ITO (Indium tin oxide)가 1500Å 두께로 박막 코팅된 유리 기판을 증류수 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 a 1500 Å thin film of ITO (indium tin oxide) was washed with distilled water ultrasonic waves. After cleaning with distilled water, ultrasonic cleaning with solvents such as isopropyl alcohol, acetone, methanol, etc., drying, transferring to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), and then cleaning the substrate using UV for 5 minutes and using a vacuum evaporator. The substrate was transferred to .
이렇게 준비된 ITO 투명 전극 위에 m-MTDATA (60 nm)/TCTA (80 nm)/ 합성예에서 합성한 각각의 화합물 + 10 % Ir(ppy)3 (300 nm)/BCP (10 nm)/Alq3 (30 nm)/LiF (1 nm)/Al (200 nm) 순으로 적층하여 유기 전계 발광 소자를 제작하였다. On the ITO transparent electrode prepared in this way, m-MTDATA (60 nm)/TCTA (80 nm)/each compound synthesized in the synthesis example + 10% Ir(ppy) 3 (300 nm)/BCP (10 nm)/Alq 3 ( An organic electroluminescent device was manufactured by stacking in the following order: 30 nm)/LiF (1 nm)/Al (200 nm).
[[ 비교예Comparative example 1] 녹색 유기 1] Green Organic 전계electric field 발광 소자의 제작 Fabrication of light emitting devices
발광층 형성시 발광 호스트 물질로서 합성예에서 합성한 화합물 대신 CBP를 사용하는 것을 제외하고는 실시예 1과 동일한 과정으로 녹색 유기 전계 발광 소자를 제작하였다.A green organic electroluminescent device was manufactured in the same process as Example 1, except that CBP was used as a light-emitting host material instead of the compound synthesized in the synthesis example when forming the light-emitting layer.
[[ 비교예Comparative example 2] 녹색 유기 2] Green Organic 전계electric field 발광 소자의 제작 Fabrication of light emitting devices
발광층 형성시 발광 호스트 물질로서 합성예에서 합성한 화합물 대신 화합물 A를 사용하는 것을 제외하고는 실시예 1과 동일한 과정으로 녹색 유기 전계 발광 소자를 제작하였다.A green organic electroluminescent device was manufactured in the same process as Example 1, except that Compound A was used as a light-emitting host material instead of the compound synthesized in the synthesis example when forming the light-emitting layer.
상기 실시예 1 내지 248, 비교예 1 및 2에서 사용된 m-MTDATA, TCTA, Ir(ppy)3, CBP, BCP 및 화합물 A의 구조는 하기와 같다.The structures of m-MTDATA, TCTA, Ir(ppy) 3 , CBP, BCP, and Compound A used in Examples 1 to 248 and Comparative Examples 1 and 2 are as follows.
[[ 평가예Evaluation example 1] One]
실시예 1 내지 248, 비교예 1 및 2 에서 제작한 각각의 녹색 유기 전계 발광 소자에 대하여 전류밀도 10 mA/㎠에서의 구동전압, 전류효율 및 발광 피크를 측정하고, 그 결과를 하기 표 2에 나타내었다.For each green organic electroluminescent device manufactured in Examples 1 to 248 and Comparative Examples 1 and 2, the driving voltage, current efficiency, and luminescence peak were measured at a current density of 10 mA/cm2, and the results are shown in Table 2 below. indicated.
(V)driving voltage
(V)
(nm)EL peak
(nm)
(cd/A)Current efficiency
(cd/A)
또한, 실시예 1, 5, 7, 10, 13, 16, 19, 22, 25, 27 및 비교예 1, 2에서 제작한 각각의 녹색 유기 전계 발광 소자에 대하여 수명(T90: 초기 휘도에서 90%로 감소하는데 소요되는 시간)을 측정하고, 그 결과를 하기 표 3에 나타내었다.In addition, for each of the green organic electroluminescent devices manufactured in Examples 1, 5, 7, 10, 13, 16, 19, 22, 25, 27 and Comparative Examples 1 and 2, the lifespan (T90: 90% from initial luminance) (time required to reduce to) was measured, and the results are shown in Table 3 below.
상기 표 2 및 3에 나타낸 바와 같이, 본 발명에 따른 화합물을 발광층에 사용한 녹색 유기 전계 발광 소자(실시예 1 내지 248)는 비교예 1 및 2에 비해 전류효율, 구동전압 및 수명면에서 보다 우수한 성능을 나타내는 것을 알 수 있었다.As shown in Tables 2 and 3, the green organic electroluminescent device (Examples 1 to 248) using the compound according to the present invention in the emitting layer is superior to Comparative Examples 1 and 2 in terms of current efficiency, driving voltage, and lifespan. performance was found to be indicative.
Claims (8)
[화학식 1]
상기 화학식 1에서,
Ar1은 하기 화학식 2 또는 화학식 3으로 표시되는 치환체이고,
Ar2는 C6~C60의 아릴기 및 핵원자수 5 내지 60의 헤테로아릴기로 이루어진 군에서 선택되고,
[화학식 2]
[화학식 3]
상기 화학식 2 및 3에서,
* 는 상기 화학식 1과 결합하는 부위를 나타내고,
X1 은 C(R1)(R2), O, S 및 N(R3)로 이루어진 군에서 선택되고,
X2 및 X3는 O이고,
R1 내지 R2는 서로 동일하거나 다르며, 각각 독립적으로 수소, 중수소(D) 및C1~C40의 알킬기로 이루어진 군에서 선택되고,
R3는 C6~C60의 아릴기 및 핵원자수 5 내지 60의 헤테로아릴기로 이루어진 군에서 선택된다.Compound represented by Formula 1:
[Formula 1]
In Formula 1,
Ar 1 is a substituent represented by Formula 2 or Formula 3 below,
Ar 2 is selected from the group consisting of an aryl group having C 6 to C 60 and a heteroaryl group having 5 to 60 nuclear atoms,
[Formula 2]
[Formula 3]
In Formulas 2 and 3,
* represents the site that binds to Formula 1 above,
X 1 is selected from the group consisting of C(R 1 )(R 2 ), O, S and N(R 3 ),
X 2 and X 3 are O,
R 1 to R 2 are the same or different from each other, and are each independently selected from the group consisting of hydrogen, deuterium (D), and C 1 to C 40 alkyl groups,
R 3 is selected from the group consisting of an aryl group having C 6 to C 60 and a heteroaryl group having 5 to 60 nuclear atoms.
상기 화학식 1로 표시되는 화합물은 하기 화학식 4 내지 7 중 적어도 어느 하나로 표시되는 것인 화합물.
[화학식 4]
[화학식 5]
[화학식 6]
[화학식 7]
상기 화학식 4 내지 7에서,
Ar1 및 Ar2는 각각 제1항에서 정의한 바와 같다.According to paragraph 1,
The compound represented by Formula 1 is a compound represented by at least one of the following Formulas 4 to 7.
[Formula 4]
[Formula 5]
[Formula 6]
[Formula 7]
In Formulas 4 to 7,
Ar 1 and Ar 2 are each as defined in paragraph 1.
상기 1층 이상의 유기물층 중 적어도 하나는 제1항 또는 제2항에 기재된 화합물을 포함하는 것인 유기 전계 발광 소자.It includes an anode, a cathode, and one or more organic layers interposed between the anode and the cathode,
An organic electroluminescent device wherein at least one of the one or more organic layers includes the compound according to claim 1 or 2.
상기 화합물을 포함하는 유기물층은 정공 주입층, 정공 수송층, 발광 보조층, 발광층, 전자 수송층 및 전자 주입층으로 이루어진 군에서 선택되는 것인 유기 전계 발광 소자.According to clause 6,
An organic electroluminescent device wherein the organic material layer containing the compound is selected from the group consisting 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.
상기 화합물을 포함하는 유기물층은 인광 발광층인 유기 전계 발광 소자.In clause 7,
An organic electroluminescent device in which the organic material layer containing the compound is a phosphorescent layer.
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