KR101652167B1 - Organic compound and organic electroluminescent device comprising the same - Google Patents
Organic compound and organic electroluminescent device comprising the same Download PDFInfo
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- KR101652167B1 KR101652167B1 KR1020140094026A KR20140094026A KR101652167B1 KR 101652167 B1 KR101652167 B1 KR 101652167B1 KR 1020140094026 A KR1020140094026 A KR 1020140094026A KR 20140094026 A KR20140094026 A KR 20140094026A KR 101652167 B1 KR101652167 B1 KR 101652167B1
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- 150000002894 organic compounds Chemical class 0.000 title claims description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 543
- 230000000903 blocking effect Effects 0.000 claims abstract description 7
- -1 alkyl boron Chemical compound 0.000 claims description 41
- 125000003118 aryl group Chemical group 0.000 claims description 37
- 125000001424 substituent group Chemical group 0.000 claims description 27
- 125000001072 heteroaryl group Chemical group 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 125000004429 atom Chemical group 0.000 claims description 18
- 125000005264 aryl amine group Chemical group 0.000 claims description 15
- 230000005525 hole transport Effects 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 7
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 7
- 229910052805 deuterium Inorganic materials 0.000 claims description 7
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 5
- 150000004982 aromatic amines Chemical class 0.000 claims description 5
- 125000005104 aryl silyl group Chemical group 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052796 boron Inorganic materials 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000006413 ring segment Chemical group 0.000 claims description 3
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims description 2
- 239000012044 organic layer Substances 0.000 abstract description 125
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 345
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 318
- 230000015572 biosynthetic process Effects 0.000 description 202
- 238000003786 synthesis reaction Methods 0.000 description 201
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- 238000006243 chemical reaction Methods 0.000 description 115
- 238000004440 column chromatography Methods 0.000 description 115
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- 239000010410 layer Substances 0.000 description 70
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- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 25
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 24
- 239000012299 nitrogen atmosphere Substances 0.000 description 22
- XSDKKRKTDZMKCH-UHFFFAOYSA-N 9-(4-bromophenyl)carbazole Chemical compound C1=CC(Br)=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 XSDKKRKTDZMKCH-UHFFFAOYSA-N 0.000 description 20
- 239000000758 substrate Substances 0.000 description 18
- 229910052757 nitrogen Inorganic materials 0.000 description 16
- 235000010290 biphenyl Nutrition 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 12
- MBHPOBSZPYEADG-UHFFFAOYSA-N 2-bromo-9,9-dimethylfluorene Chemical compound C1=C(Br)C=C2C(C)(C)C3=CC=CC=C3C2=C1 MBHPOBSZPYEADG-UHFFFAOYSA-N 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 9
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000002019 doping agent Substances 0.000 description 7
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 7
- 238000005259 measurement Methods 0.000 description 7
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 6
- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 6
- ZKGHGKNHPPZALY-UHFFFAOYSA-N 9-(3-bromophenyl)carbazole Chemical compound BrC1=CC=CC(N2C3=CC=CC=C3C3=CC=CC=C32)=C1 ZKGHGKNHPPZALY-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- FDZSMECNJPMPJD-UHFFFAOYSA-N CC1(C)c(cc(cc2)Nc(cc3)ccc3-[n]3c4ccccc4c4c3cccc4)c2-c2c1cccc2 Chemical compound CC1(C)c(cc(cc2)Nc(cc3)ccc3-[n]3c4ccccc4c4c3cccc4)c2-c2c1cccc2 FDZSMECNJPMPJD-UHFFFAOYSA-N 0.000 description 6
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 5
- FBTOLQFRGURPJH-UHFFFAOYSA-N 1-phenyl-9h-carbazole Chemical group C1=CC=CC=C1C1=CC=CC2=C1NC1=CC=CC=C12 FBTOLQFRGURPJH-UHFFFAOYSA-N 0.000 description 5
- 108010017443 B 43 Proteins 0.000 description 5
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 5
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 5
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 5
- KOFLVDBWRHFSAB-UHFFFAOYSA-N 1,2,4,5-tetrahydro-1-(phenylmethyl)-5,9b(1',2')-benzeno-9bh-benz(g)indol-3(3ah)-one Chemical compound C1C(C=2C3=CC=CC=2)C2=CC=CC=C2C23C1C(=O)CN2CC1=CC=CC=C1 KOFLVDBWRHFSAB-UHFFFAOYSA-N 0.000 description 4
- ONCCVJKFWKAZAE-UHFFFAOYSA-N 2-bromo-9,9'-spirobi[fluorene] Chemical compound C12=CC=CC=C2C2=CC=CC=C2C21C1=CC=CC=C1C1=CC=C(Br)C=C12 ONCCVJKFWKAZAE-UHFFFAOYSA-N 0.000 description 4
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 4
- LWLSVNFEVKJDBZ-UHFFFAOYSA-N N-[4-(trifluoromethoxy)phenyl]-4-[[3-[5-(trifluoromethyl)pyridin-2-yl]oxyphenyl]methyl]piperidine-1-carboxamide Chemical compound FC(OC1=CC=C(C=C1)NC(=O)N1CCC(CC1)CC1=CC(=CC=C1)OC1=NC=C(C=C1)C(F)(F)F)(F)F LWLSVNFEVKJDBZ-UHFFFAOYSA-N 0.000 description 4
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 4
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- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
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- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 4
- WNXNWOBGPRKOJF-UHFFFAOYSA-N 2-bromo-9,9-diphenylfluorene Chemical compound C12=CC(Br)=CC=C2C2=CC=CC=C2C1(C=1C=CC=CC=1)C1=CC=CC=C1 WNXNWOBGPRKOJF-UHFFFAOYSA-N 0.000 description 3
- RSQXKVWKJVUZDG-UHFFFAOYSA-N 9-bromophenanthrene Chemical compound C1=CC=C2C(Br)=CC3=CC=CC=C3C2=C1 RSQXKVWKJVUZDG-UHFFFAOYSA-N 0.000 description 3
- LMAWBUZYDZBWHF-UHFFFAOYSA-N C1=CC=C(C=C1)C2=CC=C(C=C2)N(C3=CC=C(C=C3)Cl)C4=CC5=CC=CC=C5C6=CC=CC=C64 Chemical compound C1=CC=C(C=C1)C2=CC=C(C=C2)N(C3=CC=C(C=C3)Cl)C4=CC5=CC=CC=C5C6=CC=CC=C64 LMAWBUZYDZBWHF-UHFFFAOYSA-N 0.000 description 3
- IDRGFNPZDVBSSE-UHFFFAOYSA-N OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F Chemical compound OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F IDRGFNPZDVBSSE-UHFFFAOYSA-N 0.000 description 3
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 3
- 125000005266 diarylamine group Chemical group 0.000 description 3
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
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- 125000000592 heterocycloalkyl group Chemical group 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
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- YMNJJMJHTXGFOR-UHFFFAOYSA-N n-(4-bromophenyl)-4-methyl-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(Br)=CC=1)C1=CC=C(C)C=C1 YMNJJMJHTXGFOR-UHFFFAOYSA-N 0.000 description 3
- JYAVHXABZQYLTH-UHFFFAOYSA-N n-[4-(4-bromophenyl)phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC(Br)=CC=C1C1=CC=C(N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 JYAVHXABZQYLTH-UHFFFAOYSA-N 0.000 description 3
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- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- DLKQHBOKULLWDQ-UHFFFAOYSA-N 1-bromonaphthalene Chemical compound C1=CC=C2C(Br)=CC=CC2=C1 DLKQHBOKULLWDQ-UHFFFAOYSA-N 0.000 description 2
- JBMMSVXRQPXCGP-UHFFFAOYSA-N 1-n,4-n-bis(4-methylphenyl)benzene-1,4-diamine Chemical compound C1=CC(C)=CC=C1NC(C=C1)=CC=C1NC1=CC=C(C)C=C1 JBMMSVXRQPXCGP-UHFFFAOYSA-N 0.000 description 2
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 2
- UNQZREIFLVKFAI-UHFFFAOYSA-N 2-(4-bromophenyl)-n-phenylnaphthalen-1-amine Chemical compound C1=CC(Br)=CC=C1C1=CC=C(C=CC=C2)C2=C1NC1=CC=CC=C1 UNQZREIFLVKFAI-UHFFFAOYSA-N 0.000 description 2
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- WNKOJXBCIURMOS-UHFFFAOYSA-N 2-naphthalen-1-ylbenzene-1,4-diamine Chemical compound NC1=CC=C(N)C(C=2C3=CC=CC=C3C=CC=2)=C1 WNKOJXBCIURMOS-UHFFFAOYSA-N 0.000 description 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 2
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- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
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- 229910052741 iridium Inorganic materials 0.000 description 1
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- 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
- 229910052744 lithium Inorganic materials 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
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- 150000002739 metals Chemical class 0.000 description 1
- ISXPWGFMLOCRHT-UHFFFAOYSA-N n-(4-chlorophenyl)-9,9-dimethyl-n-(4-phenylphenyl)fluoren-2-amine Chemical compound C1=C2C(C)(C)C3=CC=CC=C3C2=CC=C1N(C=1C=CC(=CC=1)C=1C=CC=CC=1)C1=CC=C(Cl)C=C1 ISXPWGFMLOCRHT-UHFFFAOYSA-N 0.000 description 1
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- NNKPHNTWNILINE-UHFFFAOYSA-N n-cyclopropyl-3-fluoro-4-methyl-5-[3-[[1-[2-[2-(methylamino)ethoxy]phenyl]cyclopropyl]amino]-2-oxopyrazin-1-yl]benzamide Chemical compound CNCCOC1=CC=CC=C1C1(NC=2C(N(C=3C(=C(F)C=C(C=3)C(=O)NC3CC3)C)C=CN=2)=O)CC1 NNKPHNTWNILINE-UHFFFAOYSA-N 0.000 description 1
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- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
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- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- ZEAWSFHWVLOENK-UHFFFAOYSA-N phenanthren-2-amine Chemical compound C1=CC=C2C3=CC=C(N)C=C3C=CC2=C1 ZEAWSFHWVLOENK-UHFFFAOYSA-N 0.000 description 1
- KIHQWOBUUIPWAN-UHFFFAOYSA-N phenanthren-9-amine Chemical compound C1=CC=C2C(N)=CC3=CC=CC=C3C2=C1 KIHQWOBUUIPWAN-UHFFFAOYSA-N 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
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- 239000007774 positive electrode material Substances 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
- 125000005581 pyrene group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
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- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
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- 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
- XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 description 1
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
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- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- BUGSVQIIKLXYBM-UHFFFAOYSA-N triphenylen-2-amine Chemical compound C1=CC=C2C3=CC(N)=CC=C3C3=CC=CC=C3C2=C1 BUGSVQIIKLXYBM-UHFFFAOYSA-N 0.000 description 1
- 125000005580 triphenylene group Chemical group 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
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
본 발명은 내열성, 정공 수송능, 전자 저지능 등이 우수한 신규 화합물을 하나 이상의 유기물층에 포함함으로써 발광효율, 구동 전압, 수명 등의 특성이 향상된 유기 전계 발광 소자에 관한 것이다.The present invention relates to an organic electroluminescent device having improved characteristics such as luminous efficiency, driving voltage and lifetime by incorporating a novel compound having excellent heat resistance, hole transporting ability, and electron blocking ability into one or more organic layers.
Description
본 발명은 신규 유기 화합물 및 이를 포함하는 유기 전계 발광 소자에 관한 것으로, 보다 구체적으로는 전자 저지능, 정공 수송능 등이 우수한 아릴아민계 화합물 및 상기 화합물을 유기물층의 재료로서 포함하여 발광효율, 구동 전압, 수명 등의 특성이 향상된 유기 전계 발광 소자에 관한 것이다.The present invention relates to a novel organic compound and an organic electroluminescent device including the same. More specifically, the present invention relates to an arylamine compound having excellent electron-blocking ability and hole-transporting ability, And lifetime of the organic electroluminescent device.
1950년대 Bernanose의 유기 박막 발광 관측을 시점으로 하여, 1965년 안트라센 단결정을 이용한 청색 전기발광으로 이어진 유기 전계 발광 (electroluminescent, EL) 소자 (이하, 간단히 '유기 EL 소자'로 칭함)에 대한 연구가 이어져 오다가, 1987년 탕(Tang)에 의하여 정공층과 발광층의 기능층으로 나눈 적층구조의 유기 EL 소자가 제시되었다. 이후 유기 EL 소자의 효율 및 수명을 향상시키기 위하여, 소자 내 특징적인 유기물층을 도입하는 형태로 발전하여 왔으며, 또한 이에 사용되는 특화된 물질의 개발로 이어졌다.A study on organic electroluminescent (EL) devices (hereinafter simply referred to as 'organic EL devices') led to blue electroluminescence using anthracene single crystals in 1965, starting from the observation of organic thin film emission of Bernanose in the 1950s In 1987, a layered organic EL device was proposed by Tang divided into a hole layer and a functional layer of a light emitting layer. In order to improve the efficiency and lifetime of the organic EL device, the organic EL device has been developed to introduce a characteristic organic material layer in the device, and development of specialized materials used thereon has been continued.
유기 전계 발광 소자는 두 전극 사이에 전압을 걸어 주면 양극에서는 정공이, 음극에서는 전자가 각각 유기물층으로 주입된다. 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 바닥 상태로 떨어질 때 빛이 나게 된다. 유기물층으로 사용되는 물질은 그 기능에 따라 발광 물질, 정공 주입 물질, 정공 수송 물질, 전자 수송 물질, 전자 주입 물질 등으로 분류될 수 있다. In the organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected into the organic layer and holes are injected into the organic layer, respectively. When the injected holes and electrons meet, an exciton is formed. When the exciton falls to the ground state, light is emitted. A material used as an organic material layer may be classified into a light emitting material, a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on its function.
발광 물질은 발광색에 따라 청색, 녹색, 적색 발광 물질로 구분될 수 있다. 그밖에, 보다 나은 천연색을 구현하기 위해 필요한 노란색 및 주황색 발광 물질로 구분될 수 있다. 또한, 색순도의 증가와 에너지 전이를 통한 발광 효율을 증가시키기 위하여, 발광 물질로서 호스트/도펀트 계를 사용할 수 있다. 도판트 물질은 유기 물질을 사용하는 형광 도판트와 Ir, Pt 등의 중원자(heavy atoms)가 포함된 금속 착체 화합물을 사용하는 인광 도판트로 나눌 수 있다. 인광 재료의 개발은 이론적으로 형광에 비해 4배까지의 발광 효율을 향상시킬 수 있기 때문에, 인광 도판트 뿐만 아니라 인광 호스트 재료들에 대해서도 관심이 집중되고 있다. The luminescent material may be classified into blue, green, and red luminescent materials depending on the luminescent color. In addition, it can be classified into yellow and orange light emitting materials necessary for realizing a better color. Further, in order to increase the color purity and increase the luminous efficiency through energy transfer, a host / dopant system can be used as a light emitting material. The dopant material can be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. The development of phosphorescent materials can theoretically improve luminescence efficiency up to four times that of fluorescence, so attention is focused on phosphorescent host materials as well as phosphorescent dopants.
현재까지 정공 주입층, 정공 수송층. 정공 차단층, 전자 수송층으로사용되는 물질로는, 하기 화학식으로 표시되는 NPB, BCP, Alq3 등이 널리 알려져 있고, 발광 물질로는 안트라센 유도체들이 형광 도판트/호스트 재료로서 보고되고 있다. 특히, 발광 물질 중 효율 향상 측면에서 큰 장점을 가지고 있는 인광 재료로는 Firpic, Ir(ppy)3, (acac)Ir(btp)2 등과 같은 Ir을 포함하는 금속 착체 화합물이 있고, 이들은 청색, 녹색, 적색 도판트 재료로 사용되고 있다. 현재까지는 CBP가 인광 호스트 재료로 우수한 특성을 나타내고 있다. Up to now, hole injecting layer, hole transporting layer. NPB, BCP, Alq 3 and the like represented by the following chemical formulas are widely known as materials used as a hole blocking layer and an electron transporting layer, and anthracene derivatives as a luminescent material have been reported as a fluorescent dopant / host material. Particularly, as a phosphorescent material having a great advantage in improving the efficiency of a light emitting material, there are metal complex compounds including Ir such as Firpic, Ir (ppy) 3 , (acac) Ir (btp) 2 , , And is used as a red dopant material. So far, CBP has shown excellent properties as a phosphorescent host material.
그러나 종래 발광 물질들은 발광특성 측면에서 양호하나, 유리전이온도 (Tg)가 낮아 열적 안정성이 매우 좋지 않기 때문에, 유기 EL 소자에서의 수명 측면에서 만족할만한 수준이 되지 못하고 있다. 따라서, 우수한 성능을 가지는 발광 물질을 포함하는 유기 전계 발광 소자의 개발이 요구되고 있다. However, conventional luminescent materials are good in terms of luminescence characteristics, but have poor thermal stability due to their low glass transition temperature (Tg), which is not satisfactory in terms of lifetime in organic EL devices. Therefore, development of an organic electroluminescent device including a luminescent material having excellent performance is required.
한편, 유기 전계 발광 소자의 실용화 및 특성 향상을 위해서, 상기와 같은 다층 구조를 갖는 유기물층으로 소자를 구성해야할 뿐만 아니라 소자의 재료, 특히 정공 수송 물질은 열적 및 전기적으로 안정적인 특성을 가지고 있어야 한다. 왜냐하면, 전압 인가시 소자에서 발생되는 열로 인하여 열안정성이 낮은 분자는 결정안정성이 낮아 재배열 현상이 일어나게 되는데, 이러한 국부적인 결정화 발생에 의해 불균질 부분이 존재하게 되고, 이러한 불균질 부분에 전기장이 집중하게 됨으로써 소자의 열화 및 파괴를 가져오기 때문이다. 따라서, 상기한 점을 고려하여 종래에 사용된 정공 수송 물질로는 m-MTDATA [4, 4′,4″-트리스(N-3-메틸페닐-N-페닐아미노)-트리페닐아민, 2-TNATA [4, 4′,4″-트리스(N-(나프틸렌-2-일)-N-페닐아미노)-트리페닐아민],TPD [N, N′-디페닐-N, N′-디(3-메틸페닐)-4, 4′-디아미노비페닐] 및 NPB [N, N′-디(나프탈렌-1-일)-N, N′-디페닐벤지딘] 등이 있다.On the other hand, in order to realize practical use and improve the characteristics of the organic electroluminescent device, it is necessary not only to constitute the device with the organic material layer having the multilayer structure, but also to have the material, particularly the hole transporting material, This is because molecules with low thermal stability due to heat generated in the device upon voltage application cause low rearrangement due to low crystal stability. Such localized crystallization causes a heterogeneous part, and an electric field This results in deterioration and destruction of the device. Therefore, in consideration of the above-mentioned points, conventionally used hole transport materials include m-MTDATA [4,4 ', 4 "-tris (N-3- methylphenyl- Triphenylamine], TPD [N, N'-diphenyl-N, N'-di ( 3-methylphenyl) -4,4'-diaminobiphenyl] and NPB [N, N'-di (naphthalen-1-yl) -N, N'-diphenylbenzidine].
그러나, m-MTDATA와 2-TNATA는 유리전이온도(Tg)가 각각 78℃ 및 108℃로 낮을 뿐만 아니라 대량화하는 과정에서 많은 문제점이 발생하기 때문에 풀 칼라를 구현하는데 문제가 있다. 또한 TPD 및 NPB도 유리전이온도(Tg)가 각각 60℃ 및 96℃로 낮기 때문에 상기와 같은 이유로 소자의 수명을 단축시킨다는 치명적인 단점이 있었다. 따라서, 열안정성을 높일 수 있고, 우수한 정공 수송 능력을 가져 유기 전계 발광 소자의 발광효율 및 전력효율을 높일 수 있는 유기 전계 발광 소자의 개발이 요구되고 있다.However, since m-MTDATA and 2-TNATA have low glass transition temperatures (Tg) of 78 ° C and 108 ° C, respectively, they cause problems in the process of mass-production. TPD and NPB also have a fatal disadvantage that the glass transition temperature (Tg) is as low as 60 캜 and 96 캜, respectively, which shortens the lifetime of the device. Therefore, development of an organic electroluminescent device capable of increasing thermal stability and having an excellent hole transporting capability and capable of increasing the luminous efficiency and power efficiency of the organic electroluminescent device is desired.
본 발명은 전자 저지능, 정공 수송능 등이 모두 우수하여 발광보조층 재료, 정공 수송층 재료, 정공 주입층 재료로 사용될 수 있는 화합물을 제공하는 것을 목적으로 한다. An object of the present invention is to provide a compound which is excellent in both electron-blocking ability and hole-transporting ability and can be used as a light-emitting auxiliary layer material, a hole transporting layer material, and a hole injection layer material.
또한 본 발명은 전술한 신규 화합물을 포함하여 구동전압이 낮고, 발광 효율이 높으며, 수명이 향상된 유기 전계 발광 소자를 제공하는 것을 또 다른 목적으로 한다.Another object of the present invention is to provide an organic electroluminescent device including the above-mentioned novel compound, which has low driving voltage, high luminous efficiency, and improved lifetime.
상기한 목적을 달성하기 위해서, 본 발명은 하기 화학식 1로 표시되는 화합물을 제공한다:In order to achieve the above object, the present invention provides a compound represented by the following formula 1:
상기 화학식 1에서,In Formula 1,
Ar1 은 하기 화학식 2로 표시되는 치환기이고,Ar 1 is a substituent represented by the following formula (2)
Ar2 내지 Ar4 는 서로 동일하거나 또는 상이하며, 각각 독립적으로 치환 또는 비치환된 C6~C60의 아릴기, 치환 또는 비치환된 핵원자수 5 내지 60의 헤테로아릴기 및 치환 또는 비치환된 C6~C60의 아릴아민기로 이루어진 군에서 선택되고,Ar 2 to Ar 4 are the same or different and each independently represents a substituted or unsubstituted C 6 to C 60 aryl group, a substituted or unsubstituted heteroaryl group having 5 to 60 ring atoms, C 6 to C 60 arylamine groups,
단, Ar2 및 Ar3 중 적어도 하나는 하기 화학식 3으로 표시되는 치환기이며; Provided that at least one of Ar 2 and Ar 3 is a substituent represented by the following formula (3);
상기 화학식 1 내지 화학식 3에서,In the above Chemical Formulas 1 to 3,
*는 결합이 이루어지는 부위이고;* Is the site where the bond is made;
R1은 서로 동일하거나 또는 상이하며, 각각 독립적으로 수소, 중수소, 치환 또는 비치환된 C1~C40의 알킬기, 치환 또는 비치환된 C6~C60의 아릴기, 치환 또는 비치환된 핵원자수 5 내지 60의 헤테로아릴기, 및 치환 또는 비치환된 C6~C60의 아릴아민기로 이루어진 군에서 선택되고, 또는 이들은 인접하는 치환기와 결합하여 축합 방향족환 또는 축합 헤테로방향족환을 형성할 수 있으며;R 1 are the same or different and are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C 1 to C 40 alkyl group, a substituted or unsubstituted C 6 to C 60 aryl group, a substituted or unsubstituted nucleus A heteroaryl group having 5 to 60 atoms and a substituted or unsubstituted C 6 to C 60 arylamine group, or they may be bonded to adjacent substituents to form a condensed aromatic ring or a condensed heteroaromatic ring ;
R2는 서로 동일하거나 또는 상이하며, 각각 독립적으로 치환 또는 비치환된 C1~C40의 알킬기, 및 치환 또는 비치환된 C6~C60의 아릴기로 이루어진 군에서 선택되고, R 2 is the same or different and is independently selected from the group consisting of a substituted or unsubstituted C 1 to C 40 alkyl group and a substituted or unsubstituted C 6 to C 60 aryl group,
n, m, l은 각각 독립적으로 1 내지 3의 정수이고;n, m and l are each independently an integer of 1 to 3;
a, b, c, d, e, f, g는 각각 독립적으로 0 내지 4의 정수이며, a, b, c, d, e, f and g are each independently an integer of 0 to 4,
상기 알킬기, 아릴기, 헤테로아릴기 및 아릴아민기가 치환될 경우는, 각각 독립적으로 중수소, 할로겐, 시아노, C1~C40의 알킬기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 구성된 군으로부터 선택되는 1종 이상으로 치환될 수 있다. 이때 복수 개의 치환기가 도입되는 경우, 복수 개의 치환기는 서로 동일하거나 또는 상이하다.When the alkyl group, an aryl group, a heteroaryl group and an arylamine group is substituted, each independently represent deuterium, halogen, cyano, C 1 ~ C 40 alkyl group, C 3 ~ C 40 cycloalkyl group, the number of nuclear atoms of 3 to the A C 6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 to C 40 alkyloxy group, a C 6 to C 60 aryloxy group, a C 3 to C 6 heteroaryl group, 40 alkylsilyl group, C 6 ~ C 60 aryl silyl group, C 1 ~ C 40 group of an alkyl boron, C 6 ~ C group 60 arylboronic of, C 6 ~ aryl phosphine of C 60 pingi, C 6 ~ C 60 aryl phosphine which may be substituted with oxide groups and at least one member selected from the group consisting of an aryl amine of the C 6 ~ C 60 of. When a plurality of substituents are introduced, the plurality of substituents 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 포함하며, 상기 1층 이상의 유기물층 중 적어도 하나는 상기 화학식 1로 표시되는 화합물을 포함하는 것을 특징으로 하는 유기 전계 발광 소자를 제공한다.In addition, cathode; And one or more organic layers sandwiched between the anode and the cathode, wherein at least one of the one or more organic layers includes a compound represented by Formula 1 .
여기서, 상기 화학식 1로 표시되는 화합물을 포함하는 1층 이상의 유기물층은 정공 수송층, 전자 저지층 및 발광보조층으로 이루어진 군에서 선택될 수 있다.
Here, the one or more organic layers including the compound represented by Formula 1 may be selected from the group consisting of a hole transport layer, an electron blocking layer, and a light-emitting auxiliary layer.
본 발명의 유기 전계 발광 소자는 내열성, 전자 저지능, 정공 수송능 등이 우수한 상기 화학식 1의 화합물을 적어도 1층 이상의 유기물층에 포함하기 때문에, 발광 성능, 구동전압, 수명, 효율 등의 측면이 크게 향상될 수 있고, 나아가 풀 칼라 디스플레이 패널 등에 효과적으로 적용될 수 있다.
Since the organic electroluminescent device of the present invention contains the compound of Formula 1 having excellent heat resistance, electron mobility and hole transport ability in at least one organic layer, it is possible to greatly improve the light emitting performance, driving voltage, And can be effectively applied to a full color display panel and the like.
이하, 본 발명에 대해 설명한다.Hereinafter, the present invention will be described.
<신규 화합물><Novel compound>
본 발명에 따른 화학식 1의 화합물은, 1개 내지 4개의 벤젠 고리를 중심으로 양쪽에 2개의 아릴아민기가 결합된 것을 기본 코어(core)로 하며, 이러한 코어(core)에 적어도 1개의 페닐카바졸 모이어티 및 1 개의 플루오렌 모이어티를 포함하여, 비대칭 구조(asymmetric structure)를 갖는 것을 특징으로 한다. The compound of formula (I) according to the present invention is characterized in that a basic core in which two arylamine groups are bonded on both sides of one to four benzene rings as a core, and at least one phenylcarbazole Moiety and a fluorene moiety, and has an asymmetric structure.
상기 화학식 1의 디아릴아민 코어(core)계 유기발광 화합물은 기존 정공 수송 재료에 비해 안정성이 좋고 재료의 수명특성이 뛰어나기 때문에 소자의 구동 수명이 매우 우수할 뿐만 아니라 전력 효율의 상승을 유도하여 소비 전력이 개선된 OLED 소자를 제조할 수 있다는 장점이 있다.The diarylamine core-based organic light emitting compound of Formula 1 has better stability and lifetime characteristics than conventional hole transporting materials, so that the device has excellent driving life and induces an increase in power efficiency There is an advantage that an OLED device with improved power consumption can be manufactured.
또한 아릴아민기, 페닐카바졸기, 플루오렌기는 각각 전자주게기(EDG) 특성을 가지므로, 안정하면서도 정공 이동도가 좋은 특성이 있다. 따라서 상기 모이어티가 비대칭 구조로 결합하고 있는 본 발명의 화학식 1로 표시되는 화합물은 열적으로 안정하고 정공 이동도를 향상시켜 효율 특성을 극대화할 수 있는 정공수송성 재료로서의 장점이 있다. Further, the arylamine group, the phenylcarbazole group and the fluorene group each have an electron donor (EDG) characteristic, so that they are stable and have good hole mobility. Accordingly, the compound represented by Formula 1 of the present invention in which the moiety is bonded in an asymmetric structure is advantageous as a hole transporting material which can thermally stabilize and improve hole mobility to maximize efficiency characteristics.
한편 발광 보조층은 삼중항 엑시톤이 Hole-related Layer로 주입되는 것을 제한하고, 동시에 일정수준 이하의 delta Est (< 0.5eV) 특성을 구비함으로써 적은 양으로 프라임(Prime)층에 유입되는 삼중항 엑시톤을 일중항 레벨로 이동시키는 역할을 할 수 있다. 이는 다시 EML의 일중항 레벨로 전이되어 엑시톤 생성에 참여시키고, 결과적으로 EML의 삼중항 레벨로 전이되어 프라임층(Prime Layer)이 구비되지 않았을 경우 발생할 수 있는 효율 손실을 없애거나, 또는 인광 발광층(EML)의 효율을 증가시키는 역할을 한다. 또한, 바람직하게는 높은 LUMO값을 나타내어 전자 저지(Electron Blocking) 기능도 포함할 수 있다. On the other hand, the light-emitting auxiliary layer limits the injection of the triplet exciton into the hole-related layer, and at the same time, has a delta Est (<0.5 eV) To the singleton level. It is then transferred back to the singlet level of the EML to participate in the exciton generation and consequently transition to the triplet level of the EML to eliminate the efficiency loss that would otherwise occur if the prime layer is not provided, EML). ≪ / RTI > Further, it preferably exhibits a high LUMO value and may also include an electron blocking function.
아울러, 형광 청색소자의 효율을 높이기 위해 사용되며, 그 역할은 일정수준 이상의 정공 이동도(Hole mobility)를 가지며(higher than Hole Mobility of NPB), T1값이 청색 형광 발광층 보다 높아서, 삼중항 여기자가 BIL로 유입되는 것을 막고, 발광층 안에 제한시켜 TTA(TTF)를 통해 삼중항 여기자가 일중항 여기자로 변환하도록 하여 효율을 높이는 역할이 주된 역할이다. 이때, 바람직하게는 BIL이 Hole-related layer와 발광층(EML)간의 계면특성 향상 효과도 동반 수반할 수 있으며, 더 바람직하게는 높은 LUMO값을 나타내어 전자 저지(Electron Blocking) 기능도 포함할 수 있다. In addition, it is used to increase the efficiency of the fluorescent blue element. Its role is to have a hole mobility of higher than a certain level (Hole Mobility of NPB) and a value of T1 higher than that of the blue fluorescent light emitting layer. The main role is to prevent the entry into the BIL, limit its activity to the light emitting layer, and convert the triplet exciton into singlet exciton through TTA (TTF) to increase the efficiency. At this time, preferably, BIL may also have an effect of improving the interface characteristics between the hole-related layer and the emission layer (EML), more preferably exhibiting a high LUMO value, and may also include an electron blocking function.
나아가, 본 발명에 따른 화학식 1로 표시되는 화합물은 페닐, 비페닐, 터페닐에 아릴아민기가 결합하여 전자가 풍부(electron rich)한 기본 구조를 가지고, 정공 이동도가 뛰어나며 높은 삼중항에너지를 갖는 카바졸 모이어티, 플루오렌 모이어티를 포함하므로 효율 특성을 극대화할 수 있는 발광보조층 재료로써의 장점이 있다.
Further, the compound represented by the formula (1) according to the present invention has a basic structure in which phenyl, biphenyl, terphenyl and arylamine groups are bonded to form an electron rich structure, and has excellent hole mobility and high triplet energy A carbazole moiety, and a fluorene moiety, which is advantageous as a light emitting auxiliary layer material capable of maximizing efficiency characteristics.
본 발명에 따라 화학식 1로 표시되는 화합물에서, Ar1은 상기 화학식 2 표시되는 페닐카바졸 계열 치환기를 가지며, Ar2와 Ar3 중 적어도 하나는 상기 화학식 3으로 표시되는 플루오렌 계열 치환기를 갖는다. 여기서, *는 결합이 이루어지는 부위를 의미한다. According to the present invention, in the compound represented by the general formula (1), Ar 1 has a phenylcarbazole-based substituent represented by the general formula (2), and at least one of Ar 2 and Ar 3 has a fluorene-based substituent represented by the general formula (3). Here, * denotes a site where bonding is performed.
본 발명에서, 상기 화학식 3의 치환기를 갖지 않는 Ar2 내지 Ar4 는 서로 동일하거나 또는 상이하며, 각각 독립적으로 치환 또는 비치환된 C6~C60의 아릴기, 치환 또는 비치환된 핵원자수 5 내지 60의 헤테로아릴기 및 치환 또는 비치환된 C6~C60의 아릴아민기로 이루어진 군에서 선택된다. 보다 구체적으로, 상기 C6~C60의 아릴기는 페닐기, 비페닐기, 나프틸기, 페난트렌기, 파이렌기, 트리페닐렌기, 플루오렌기 등에서 선택될 수 있으며, 상기 핵원자수 5 내지 60의 헤테로아릴기는 피리딘, 피리미딘, 트리아진, 퀴나졸린, 카바졸, 디벤조퓨란, 디벤조싸이오펜 등에서 선택될 수 있다. 또한 C6~C60의 아릴아민기는 상기의 아릴기, 헤테로아릴기가 치환된 아민기에서 선택될 수 있으나, 이에 특별히 한정되는 것은 아니다.In the present invention, Ar 2 to Ar 4 having no substituent in Formula 3 are the same or different and each independently represents a substituted or unsubstituted C 6 to C 60 aryl group, a substituted or unsubstituted nucleus atom of 5 to 60 heteroaryl group, and is selected from the group consisting of arylamine-substituted or unsubstituted C 6 ~ C 60. More specifically, the C 6 -C 60 aryl group may be selected from a phenyl group, a biphenyl group, a naphthyl group, a phenanthrene group, a pyrene group, a triphenylene group, a fluorene group, The aryl group may be selected from pyridine, pyrimidine, triazine, quinazoline, carbazole, dibenzofuran, dibenzothiophene and the like. The arylamine group of C 6 to C 60 may be selected from the above-mentioned aryl group and an amine group substituted by a heteroaryl group, but is not particularly limited thereto.
이때, 상기 Ar2 내지 Ar4는 각각 독립적으로 치환 또는 비치환된 C6~C60의 아릴기, 치환 또는 비치환된 핵원자수 5 내지 60의 헤테로아릴기인 경우가 바람직하다. In this case, each of Ar 2 to Ar 4 is independently a substituted or unsubstituted C 6 to C 60 aryl group, or a substituted or unsubstituted heteroaryl group having 5 to 60 nucleus atoms.
R1은 서로 동일하거나 또는 상이하며, 각각 독립적으로 수소, 중수소, 치환 또는 비치환된 C1~C40의 알킬기, 치환 또는 비치환된 C6~C60의 아릴기, 치환 또는 비치환된 핵원자수 5 내지 60의 헤테로아릴기, 및 치환 또는 비치환된 C6~C60의 아릴아민기로 이루어진 군에서 선택되고, 또는 이들은 인접하는 치환기와 결합하여 축합 방향족환 또는 축합 헤테로방향족환을 형성할 수 있다. R 1 are the same or different and are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C 1 to C 40 alkyl group, a substituted or unsubstituted C 6 to C 60 aryl group, a substituted or unsubstituted nucleus A heteroaryl group having 5 to 60 atoms and a substituted or unsubstituted C 6 to C 60 arylamine group, or they may be bonded to adjacent substituents to form a condensed aromatic ring or a condensed heteroaromatic ring .
R2는 서로 동일하거나 또는 상이하며, 각각 독립적으로 치환 또는 비치환된 C1~C40의 알킬기, 치환 또는 비치환된 C6~C60의 아릴기로 이루어진 군에서 선택된다. R 2 are the same or different and each independently selected from the group consisting of a substituted or unsubstituted C 1 to C 40 alkyl group, and a substituted or unsubstituted C 6 to C 60 aryl group.
여기서, 상기 R2는 메틸기, 페닐기, (*는 결합이 이루어지는 부위)인 경우가 바람직하다.Herein, R 2 represents a methyl group, a phenyl group, (* Is a site where bonding is performed).
n, m, l은 각각 독립적으로 1 내지 3의 정수이고;n, m and l are each independently an integer of 1 to 3;
a, b, c, d, e, f, g는 각각 독립적으로 0 내지 4의 정수이다. a, b, c, d, e, f and g are each independently an integer of 0 to 4;
본 발명에서, "치환 또는 비치환된" 이라는 용어가 기재된 치환기, 즉 알킬기, 아릴기, 헤테로아릴기 및 아릴아민기가 치환될 경우는, 각각 독립적으로 중수소, 할로겐, 시아노, C1~C40의 알킬기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 구성된 군으로부터 선택되는 1종 이상으로 치환될 수 있다. 이때 복수 개의 치환기가 도입되는 경우, 복수 개의 치환기는 서로 동일하거나 또는 상이하다.In the present invention, the substituents described the term "substituted or unsubstituted", that is an alkyl group, an aryl group, a heteroaryl group, and aryl amine groups are each independently selected from deuterium, halogen, cyano, C 1 ~ C 40 when substituted the alkyl group, C 3 ~ C 40 cycloalkyl group, the number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 6 ~ of the C 60 aryl group, the nuclear atoms of 5 to 60 heteroaryl group, C 1 ~ C 40 alkyl aryloxy group, C 6 ~ aryloxy C 60, C group 3 ~ C 40 alkylsilyl, C 6 ~ C aryl silyl group of 60, C 1 ~ C 40 group of an alkyl boron, C 6 ~ aryl of C 60 boron group, may be substituted with a C 6 ~ C 60 aryl phosphine group of, C 6 ~ C 60 aryl phosphine oxide group, and a C 6 ~ at least one member selected from the group consisting of an aryl amine of the C 60. When a plurality of substituents are introduced, the plurality of substituents may be the same or different from each other.
본 발명에서, 상기 화학식 1로 표시되는 화합물은 하기 화학식 4 또는 화학식 5 중 어느 하나로 표시되는 화합물로 보다 구체화될 수 있다. In the present invention, the compound represented by the formula (1) may be further represented by a compound represented by the following formula (4) or (5).
여기서, 화학식 4는 디아릴아민 코어를 중심으로 일측의 아민기에 페닐카바졸 모이어티와 플루오렌 모이어티가 모두 결합된 비대칭 구조를 나타낸다(즉, Ar2가 화학식 3의 구조를 가짐). 또한 화학식 5는 디아릴아민 코어를 중심으로 양측의 아민기에 페닐카바졸 모이어티와 플루오렌 모이어티가 각각 하나씩 결합되어 있는 비대칭 구조를 나타낸다(즉, Ar3가 화학식 3의 구조를 가짐). (4) represents an asymmetric structure in which both phenylcarbazole moiety and fluorene moiety are bonded to one side of the diarylamine core (i.e., Ar 2 has the structure of formula (3)). (5) shows an asymmetric structure in which a phenylcarbazole moiety and a fluorene moiety are bonded to each other at both side of the diarylamine core (i.e., Ar 3 has a structure of the formula (3)).
상기 화학식 4 또는 화학식 5에서, In Formula 4 or Formula 5,
Ar2 ~ Ar4, R1~R2, a~f는 각각 화학식 1에서 정의된 바와 같다. Ar 2 to Ar 4 , R 1 to R 2 , and a to f are each as defined in formula (1).
본 발명의 바람직한 일례를 들면, 화학식 3의 치환기 구조를 갖지 않는 Ar2 내지 Ar4는 서로 동일하거나 또는 상이하며, 각각 독립적으로 치환 또는 비치환된 C6~C60의 아릴기, 치환 또는 비치환된 핵원자수 5 내지 60의 헤테로아릴기로 이루어진 군에서 선택되고,As a preferred example of the present invention, Ar 2 to Ar 4 which do not have a substituent structure of the general formula (3) are the same or different and each independently represents a substituted or unsubstituted C 6 to C 60 aryl group, And a heteroaryl group having 5 to 60 nuclear atoms,
R1는 서로 동일하거나 또는 상이하며, 각각 독립적으로 수소, 치환 또는 비치환된 C1~C40의 알킬기, 치환 또는 비치환된 C6~C60의 아릴기, 치환 또는 비치환된 핵원자수 5 내지 60의 헤테로아릴기, 및 치환 또는 비치환된 C6~C60의 아릴아민기로 이루어진 군에서 선택되고,R 1 are the same or different and each independently represents hydrogen, a substituted or unsubstituted C 1 to C 40 alkyl group, a substituted or unsubstituted C 6 to C 60 aryl group, a substituted or unsubstituted nucleus atom number 5 to 60 heteroaryl groups, and substituted or unsubstituted C 6 to C 60 arylamine groups,
R2는 서로 동일하거나 또는 상이하며, 각각 독립적으로 메틸기, 페닐기, 이며, (이때 *는 결합이 이루어지는 부위를 의미하며),R 2 are the same or different and each independently represents a methyl group, a phenyl group, (Where * denotes a site where bonding occurs),
n, m, l은 각각 독립적으로 1 내지 3의 정수이고;n, m and l are each independently an integer of 1 to 3;
a, b, c, d, e, f, g는 각각 독립적으로 0 내지 4의 정수이며, a, b, c, d, e, f and g are each independently an integer of 0 to 4,
상기 알킬기, 아릴기, 헤테로아릴기 및 아릴아민기가 치환될 경우는, 각각 독립적으로 중수소, 할로겐, 시아노, C1~C40의 알킬기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 구성된 군으로부터 선택되는 1종 이상으로 치환될 수 있다. 이때 복수 개의 치환기가 도입되는 경우, 복수 개의 치환기는 서로 동일하거나 또는 상이하다.When the alkyl group, an aryl group, a heteroaryl group and an arylamine group is substituted, each independently represent deuterium, halogen, cyano, C 1 ~ C 40 alkyl group, C 3 ~ C 40 cycloalkyl group, the number of nuclear atoms of 3 to the A C 6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 to C 40 alkyloxy group, a C 6 to C 60 aryloxy group, a C 3 to C 6 heteroaryl group, 40 alkylsilyl group, C 6 ~ C 60 aryl silyl group, C 1 ~ C 40 group of an alkyl boron, C 6 ~ C group 60 arylboronic of, C 6 ~ aryl phosphine of C 60 pingi, C 6 ~ C 60 aryl phosphine which may be substituted with oxide groups and at least one member selected from the group consisting of an aryl amine of the C 6 ~ C 60 of. When a plurality of substituents are introduced, the plurality of substituents may be the same or different from each other.
이상에서 설명한 본 발명의 화합물은 하기 예시되는 화학식 A-1 내지 화학식 B-96 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 of the present invention described above can be further compounded into a compound represented by any of the following formulas A-1 to B-96 shown below. However, the compounds represented by formula (1) of the present invention are not limited by the following examples.
본 발명에서의 알킬은 탄소수 1 내지 40의 직쇄 또는 측쇄의 포화 탄화수소에서 유래되는 1가의 치환기이며, 이의 예로는 메틸, 에틸, 프로필, 이소부틸, sec-부틸, 펜틸, iso-아밀, 헥실 등이 있는데, 이에 한정되지 않는다.In the present invention, alkyl is a monovalent substituent derived from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms, and examples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, However, the present invention is not limited thereto.
본 발명에서의 알케닐(alkenyl)은 탄소-탄소 이중 결합을 1개 이상 가진 탄소수 2 내지 40의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기이며, 이의 예로는 비닐(vinyl), 알릴(allyl), 이소프로펜일(isopropenyl), 2-부텐일(2-butenyl) 등이 있는데, 이에 한정되지 않는다.The alkenyl in the present invention is a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon double bond. Examples thereof include vinyl, allyl, Isopropenyl, 2-butenyl, and the like, but the present invention is not limited thereto.
본 발명에서의 알키닐(alkynyl)은 탄소-탄소 삼중 결합을 1개 이상 가진 탄소수 2 내지 40의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기이며, 이의 예로는 에티닐(ethynyl), 2-프로파닐(2-propynyl) 등이 있는데, 이에 한정되지 않는다.Alkynyl in the present invention is a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon triple bond. Examples thereof include ethynyl, 2- 2-propynyl, and the like, but are not limited thereto.
본 발명에서의 아릴은 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 등이 있는데, 이에 한정되지 않는다.The aryl in the present invention means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms in which a single ring or two or more rings are combined. Also, a form in which two or more rings are pendant or condensed with each other may be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.
본 발명에서의 헤테로아릴은 핵원자수 5 내지 40의 모노헤테로사이클릭 또는 폴리헤테로사이클릭 방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 이때, 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3개의 탄소가 N, O, S 또는 Se와 같은 헤테로원자로 치환된다. 또한, 2이상의 고리가 서로 단순 부착(pendant)되거나 축합된 형태도 포함될 수 있고, 나아가 아릴기와의 축합된 형태도 포함하는 것으로 해석한다. 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; 2-퓨라닐, N-이미다졸릴, 2-이속사졸릴, 2-피리디닐, 2-피리미디닐 등이 있는데, 이에 한정되지 않는다.The heteroaryl in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclear atoms. Wherein at least one of the carbons, preferably one to three carbons, is replaced by a heteroatom such as N, O, S or Se. In addition, it is understood that a form in which two or more rings are pendant or condensed with each other may be included, and further includes a condensed form with an aryl group. Examples of such heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; Such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, and the like. ring; Imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.
본 발명에서의 아릴옥시는 RO-로 표시되는 1가의 치환기로 상기 R은 탄소수 6 내지 60의 아릴을 의미한다. 이러한 아릴옥시의 예로는 페닐옥시, 나프틸옥시, 디페닐옥시 등이 있는데, 이에 한정되지 않는다.In the present invention, aryloxy is a monovalent substituent represented by RO-, and R represents aryl having 6 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.
본 발명에서의 알킬옥시는 R'O-로 표시되는 1가의 치환기로 상기 R'는 1 내지 40개의 알킬을 의미하며, 직쇄(linear), 측쇄(branched) 또는 사이클릭(cyclic) 구조를 포함하는 것으로 해석한다. 이러한 알킬옥시의 예로는 메톡시, 에톡시, n-프로폭시, 1-프로폭시, t-부톡시, n-부톡시, 펜톡시 등이 있는데, 이에 한정되지 않는다.The alkyloxy in the present invention is a monovalent substituent group represented by R'O-, wherein R 'is an alkyl having 1 to 40 carbon atoms and includes a linear, branched or cyclic structure . Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.
본 발명에서의 아릴아민은 탄소수 6 내지 60의 아릴로 치환된 아민을 의미한다.The arylamine in the present invention means an amine substituted with aryl having 6 to 60 carbon atoms.
본 발명에서의 시클로알킬은 탄소수 3 내지 40의 모노사이클릭 또는 폴리사이클릭 비-방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 이러한 사이클로알킬의 예로는 사이클로프로필, 사이클로펜틸, 사이클로헥실, 놀보닐(norbornyl), 아다만틴(adamantine) 등이 있는데, 이에 한정되지 않는다.The cycloalkyl in the present invention means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyls include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
본 발명에서의 헤테로시클로알킬은 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 등이 있는데, 이에 한정되지 않는다.Heterocycloalkyl in the present invention means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, wherein at least one carbon of the ring, preferably 1 to 3 carbons, is N, O, S or Se. ≪ / RTI > Examples of such heterocycloalkyls include, but are not limited to, morpholine, piperazine, and the like.
본 발명에서의 알킬실릴은 탄소수 1 내지 40의 알킬로 치환된 실릴이고, 아릴실릴은 탄소수 6 내지 40의 아릴로 치환된 실릴을 의미한다.The alkylsilyl in the present invention is silyl substituted with alkyl having 1 to 40 carbon atoms, and arylsilyl means silyl substituted with aryl having 6 to 40 carbon atoms.
본 발명에서의 축합 고리는 축합 지방족 고리, 축합 방향족 고리, 축합 헤테로지방족 고리, 축합 헤테로방향족 고리 또는 이들의 조합된 형태를 의미한다.The condensed ring in the present invention means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.
본 발명의 화학식 1의 화합물은 일반적인 합성방법에 따라 합성될 수 있다(Chem. Rev., 60:313 (1960); J. Chem. SOC. 4482 (1955); Chem. Rev. 95: 2457 (1995) 등 참조). 본 발명의 화합물에 대한 상세한 합성 과정은 후술하는 합성예에서 구체적으로 기술하도록 한다.
The compounds of formula 1 of the present invention can be synthesized according to the general synthetic methods ( Chem. Rev. , 60 : 313 (1960); J. Chem. SOC . 4482 (1955); Chem. Rev. 95: 2457 (1995 ). Detailed synthesis of the compound of the present invention will be described in detail in Synthesis Examples to be described later.
<유기 전계 발광 소자>≪ Organic electroluminescent device &
한편, 본 발명의 다른 측면은 상기한 본 발명에 따른 화학식 1로 표시되는 화합물을 포함하는 유기 전계 발광 소자(유기 EL 소자)에 관한 것이다.Another aspect of the present invention relates to an organic electroluminescent device (organic EL device) comprising the compound represented by the general formula (1) according to the present invention described 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 at least one anode, an anode, and at least one organic layer sandwiched between the anode and the cathode, and at least one of the one or more organic layers Include the compounds represented by the above formula (1). At this time, the compounds may be used alone or in combination of two or more.
상기 1층 이상의 유기물층은 정공주입층, 정공수송층, 발광보조층, 발광층, 전자수송층 및 전자주입층 중 어느 하나 이상일 수 있고, 이 중에서 적어도 하나의 유기물층은 상기 화학식 1로 표시되는 화합물을 포함할 수 있다. 구체적으로 상기 화학식 1의 화합물을 포함하는 유기물층은 정공수송층, 전자 저지층 또는 발광보조층인 것이 바람직하다.The at least one organic material layer may include at least one of a hole injecting layer, a hole transporting layer, a light emitting auxiliary layer, a light emitting layer, an electron transporting layer, and an electron injecting layer. have. Specifically, it is preferable that the organic material layer containing the compound of Formula 1 is a hole transport layer, an electron blocking layer, or a light-emitting auxiliary layer.
본 발명의 유기 전계 발광 소자의 발광층은 호스트 재료를 포함할 수 있는데, 이때 호스트 재료로서 상기 화학식 1의 화합물을 포함할 수 있다. The light emitting layer of the organic electroluminescent device of the present invention may include a host material, and may include the compound of Formula 1 as a host material.
본 발명에 따른 화학식 1로 표시되는 화합물은 페닐, 비페닐, 터페닐에 아릴아민기가 결합하여 전자가 풍부(electron rich)한 기본 구조를 가지고, 정공 이동도가 뛰어나며 높은 삼중항에너지를 갖는 카바졸 모이어티, 플루오렌 모이어티를 포함하므로, 효율 특성을 극대화할 수 있는 발광보조층 재료로써의 장점이 있다.The compound represented by formula (1) according to the present invention has a basic structure in which phenyl, biphenyl and terphenyl arylamine groups are bonded to form an electron rich structure, and has a high hole mobility and a high trivalent energy. Moiety, fluorene moiety, and thus has an advantage as a light emitting auxiliary layer material capable of maximizing the efficiency characteristics.
이러한 본 발명의 유기 전계 발광 소자의 구조는 특별히 한정되지 않으나, 기판, 양극, 정공주입층, 정공수송층, 발광보조층, 발광층, 전자수송층 및 음극이 순차적으로 적층된 구조일 수 있다. 이때, 상기 정공주입층, 정공수송층, 발광보조층, 발광층, 전자수송층 및 전자주입층 중 하나 이상은 상기 화학식 1로 표시되는 화합물을 포함할 수 있고, 바람직하게는 정공수송층, 전자저지층, 발광보조층이 상기 화학식 1로 표시되는 화합물을 포함할 수 있다. 한편 상기 전자수송층 위에는 전자주입층이 추가로 적층될 수 있다.The structure of the organic electroluminescent device of the present invention is not particularly limited, but may be a structure in which a substrate, an anode, a hole injecting layer, a hole transporting layer, a light emitting auxiliary layer, a light emitting layer, an electron transporting layer and a cathode are sequentially laminated. At least one of the hole injecting layer, the hole transporting layer, the light emitting auxiliary layer, the light emitting layer, the electron transporting layer, and the electron injecting layer may include the compound represented by Formula 1, and preferably includes a hole transporting layer, The auxiliary layer may include a compound represented by the above formula (1). On the other hand, an electron injection layer may be further stacked on the electron transport layer.
본 발명의 유기 전계 발광 소자의 구조는 전극과 유기물층 계면에 절연층 또는 접착층이 삽입된 구조일 수 있다.The structure of the organic electroluminescent device of the present invention may be a structure in which an insulating layer or an adhesive layer is inserted into the interface between the electrode and the organic layer.
본 발명의 유기 전계 발광 소자는 상기 유기물층 중 1층 이상이 상기 화학식 1로 표시되는 화합물을 포함하는 것을 제외하고는, 당업계에 공지된 재료 및 방법으로 유기물층 및 전극을 형성하여 제조할 수 있다.The organic electroluminescent device of the present invention can be produced by forming an organic material layer and an electrode by materials and methods known in the art, except that at least one of the organic material layers includes the compound represented by the above formula (1).
상기 유기물층은 진공 증착법이나 용액 도포법에 의하여 형성될 수 있다. 상기 용액 도포법의 예로는 스핀 코팅, 딥코팅, 닥터 블레이딩, 잉크젯 프린팅 또는 열 전사법 등이 있으나, 이에 한정되지는 않는다.The organic material layer may be formed by a vacuum deposition method or a solution coating method. Examples of the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.
본 발명의 유기 전계 발광 소자 제조 시 사용되는 기판은 특별히 한정되지 않으나, 실리콘 웨이퍼, 석영, 유리판, 금속판, 플라스틱 필름 및 시트 등을 사용할 수 있다.The substrate used in the fabrication of the organic electroluminescent device of the present invention is not particularly limited, but silicon wafer, quartz, glass plate, metal plate, plastic film and sheet can be used.
또, 양극 물질로는 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연산화물, 인듐산화물, 인듐 주석 산화물(ITO), 인듐 아연 산화물(IZO)과 같은 금속 산화물; ZnO:Al 또는 SnO2:Sb와 같은 금속과 산화물의 조합; 폴리티오펜, 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜](PEDT), 폴리피롤 또는 폴리아닐린과 같은 전도성 고분자; 및 카본블랙 등을 들 수 있으나, 이에 한정되지는 않는다.Examples of the positive electrode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO 2: a combination of a metal and an oxide such as Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole or polyaniline; And carbon black, but are not limited thereto.
또, 음극 물질로는 마그네슘, 칼슘, 나트륨, 칼륨, 타이타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석, 또는 납과 같은 금속 또는 이들의 합금; 및 LiF/Al 또는 LiO2/Al과 같은 다층 구조 물질 등을 들 수 있으나, 이에 한정되지는 않는다.The negative electrode material may be a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin or lead or an alloy thereof; And multi-layer structure materials such as LiF / Al or LiO 2 / Al, 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.The hole injecting layer, the hole transporting layer, the electron injecting layer and the electron transporting layer are not particularly limited, and ordinary 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 with reference to examples. However, the following examples are illustrative of the present invention, and the present invention is not limited by the following examples.
[준비예 1] [Preparation Example 1] N-(4-(9H-carbazol-9-yl)phenyl)-9,9-dimethyl-9H-fluoren-2-amine의 합성Synthesis of N- (4- (9H-carbazol-9-yl) phenyl) -9,9-dimethyl-9H-fluoren-
질소 기류 하에서 50.0 g(238.90 mmol)의 9-(4-bromophenyl)-9H-carbazole, 43.94 g(262.79 mmol)의 9,9-dimethyl-9H-fluoren-2-amine, 6.56 g(7.17 mmol)의 Pd2(dba)3, 4.84 g(23.89 mmol)의 P(t-bu)3, 57.40 g(597.26 mmol)의 NaO(t-bu) 및 toluene (1000 ml)를 혼합하고 110℃에서 5시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 80.73 g (yield: 75 %)을 획득하였다. 9.9-dimethyl-9H-fluoren-2-amine, 6.56 g (7.17 mmol) of 9- (4-bromophenyl) -9H-carbazole, 43.94 g (262.79 mmol) of 50.0 g (238.90 mmol) mixture of Pd 2 (dba) 3, 4.84 g NaO (t-bu) , and toluene (1000 ml) of P (t-bu) 3, 57.40 g (597.26 mmol) of (23.89 mmol), and for 5 hours at 110 ℃ Lt; / RTI > After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 80.73 g (yield: 75%) of the target compound was obtained by column chromatography.
GC-Mass (이론치: 450.57 g/mol, 측정치: 450 g/mol)GC-Mass (calculated: 450.57 g / mol, measured: 450 g / mol)
1H-NMR: δ 1.70 (s, 6H), 4.00 (s, 1H), 6.30 (m, 3H), 7.37 (m, 7H), 7.65 (m, 4H), 7.90 (m, 2H), 8.15 (d, 1H), 8.55 (d, 1H)
(M, 2H), 7.90 (m, 2H), 8.15 (d, 2H), 7.30 , ≪ / RTI > 1H), 8.55 (d, 1H)
[준비예 2] [Preparation Example 2] N-(4-chlorophenyl)-[1,1'-biphenyl]-4-amine의 합성Synthesis of N- (4-chlorophenyl) - [1,1'-biphenyl] -4-amine
질소 기류 하에서 80.0 g(335.50 mmol)의 1-chloro-4-iodobenzene, 56.77 g(169.22 mmol)의 [1,1'-biphenyl]-4-amine, 9.22 g(10.07 mmol)의 Pd2(dba)3, 6.79 g(33.55 mmol)의 P(t-bu)3, 80.60 g(838.75 mmol)의 NaO(t-bu) 및 toluene (1000 ml)를 혼합하고 110℃에서 5시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터링된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 58.1 g (yield: 62 %)을 획득하였다. 1-chloro-4-iodobenzene, 56.77 g (169.22 mmol) of [l, l'-biphenyl] -4-amine and 9.22 g (10.07 mmol) of Pd 2 (dba) 3, 6.79 g (33.55 mmol) of P (t-bu) 3, 80.60 g (838.75 mmol) of NaO (t-bu) and toluene (1000 ml) were mixed and stirred at 110 ° C for 5 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 58.1 g (yield: 62%) of the desired compound was obtained by column chromatography.
GC-Mass (이론치: 279.76 g/mol, 측정치: 279 g/mol)GC-Mass (calculated: 279.76 g / mol, measured: 279 g / mol)
1H-NMR: δ 4.0 (s, 1H), 6.50 (d, 2H), 7.30 (d, 2H), 7.54 (m, 7H), 7.66 (d, 2H)
2H), 7.54 (m, 7H), 7.66 (d, 2H), 7.50 (d,
[준비예 3] [Preparation Example 3] N-([1,1'-biphenyl]-4-yl)-N-(4-chlorophenyl)phenanthren-2-amine의 합성Synthesis of N - ([1,1'-biphenyl] -4-yl) -N- (4-chlorophenyl) phenanthren-
질소 기류 하에서 준비예 2 에서 합성된 화합물 10.0 g (35.74 mmol), 9.19 g(35.74 mmol)의 2-bromophenanthrene, 0.98 g(1.07 mmol)의 Pd2(dba)3, 0.72 g(3.57 mmol)의 P(t-bu)3, 8.59 g(89.36 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터링된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 11.40 g (yield: 70 %)을 획득하였다.2-bromophenanthrene, 0.98 g (1.07 mmol) of Pd 2 (dba) 3 and 0.72 g (3.57 mmol) of the compound synthesized in Preparation Example 2 (10.0 g, 35.74 mmol) and 9.19 g (t-bu) 3, 8.59 g (89.36 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 11.40 g (yield: 70%) of the desired compound was obtained by column chromatography.
GC-Mass (이론치: 455.98 g/mol, 측정치: 455 g/mol)GC-Mass (theory: 455.98 g / mol, measured: 455 g / mol)
1H-NMR: δ 6.50 (d, 2H), 6.69 (d, 2H), 7.10 (d, 1H), 7.30 (d, 2H), 7.32 (d, 1H), 7.50 (m, 7H), 7.70 (d, 2H), 7.80 (t, 2H), 8.20 (d, 1H) , 8.50 (d, 1H), 8.92 (d, 1H)
(D, 2H), 7.50 (d, 2H), 7.69 (d, 2H) , 8.80 (d, IH), 8.50 (d, IH), 8.92 (d,
[준비예 4] [Preparation Example 4] N-([1,1'-biphenyl]-4-yl)-N-(4-chlorophenyl)phenanthren-9-amine의 합성Synthesis of N - ([1,1'-biphenyl] -4-yl) -N- (4-chlorophenyl) phenanthren-9-amine
질소 기류 하에서 준비예 2 에서 합성된 화합물 10.0 g (35.74 mmol), 9.19 g(35.74 mmol)의 9-bromophenanthrene, 0.98 g(1.07 mmol)의 Pd2(dba)3, 0.72 g(3.57 mmol)의 P(t-bu)3, 8.59 g(89.36 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 12.22 g (yield: 75 %)을 획득하였다.9.0 g (35.74 mmol) of 9-bromophenanthrene, 0.98 g (1.07 mmol) of Pd 2 (dba) 3 and 0.72 g (3.57 mmol) of the compound synthesized in Preparation Example 2 (t-bu) 3, 8.59 g (89.36 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 12.22 g (yield: 75%) of the desired compound was obtained by column chromatography.
GC-Mass (이론치: 455.98 g/mol, 측정치: 455 g/mol)GC-Mass (theory: 455.98 g / mol, measured: 455 g / mol)
1H-NMR: δ 6.50 (d, 2H), 6.69 (d, 2H), 7.10 (d, 1H), 7.30 (d, 2H), 7.32 (d, 1H), 7.50 (m, 7H), 7.70 (d, 2H), 7.80 (t, 2H), 8.20 (d, 1H) , 8.50 (d, 1H), 8.92 (d, 1H)
(D, 2H), 7.50 (d, 2H), 7.69 (d, 2H) , 8.80 (d, IH), 8.50 (d, IH), 8.92 (d,
[준비예 5] [Preparation Example 5] N-([1,1'-biphenyl]-4-yl)-N-(4-chlorophenyl)triphenylen-2-amine의 합성Synthesis of N - ([1,1'-biphenyl] -4-yl) -N- (4-chlorophenyl) triphenylen-2-amine
질소 기류 하에서 준비예 2 에서 합성된 화합물 10.0 g (35.74 mmol), 10.98 g(35.74 mmol)의 2-bromotriphenylene, 0.98 g(1.07 mmol)의 Pd2(dba)3, 0.72 g(3.57 mmol)의 P(t-bu)3, 8.59 g(89.36 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 12.66 g (yield: 70 %)을 획득하였다.2-bromotriphenylene, 0.98 g (1.07 mmol) of Pd 2 (dba) 3 and 0.72 g (3.57 mmol) of the compound synthesized in Preparation Example 2 (10.0 g, 35.74 mmol) and 10.98 g (t-bu) 3, 8.59 g (89.36 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 12.66 g (yield: 70%) of the desired compound was obtained by column chromatography.
GC-Mass (이론치: 506.04 g/mol, 측정치: 506 g/mol)GC-Mass (calculated: 506.04 g / mol, measured: 506 g / mol)
1H-NMR: δ 6.50 (d, 2H), 6.69 (d, 2H), 7.05 (d, 1H), 7.24 (d, 2H), 7.50 (m, 7H), 7.75 (m, 5H), 7.80 (m, 3H), 8.90 (d, 2H)
(D, 2H), 7.50 (m, 5H), 7.75 (m, 5H), 7.80 (d, 2H) , ≪ / RTI > 3H), 8.90 (d, 2H)
[준비예 6] [Preparation Example 6] N-([1,1'-biphenyl]-4-yl)-N-(4-chlorophenyl)naphthalen-1-amine의 합성Synthesis of N - ([1,1'-biphenyl] -4-yl) -N- (4-chlorophenyl) naphthalen-
질소 기류 하에서 준비예 2 에서 합성된 화합물 10.0 g (35.74 mmol), 13.55 g(35.74 mmol)의 1-bromonaphthalene, 0.98 g(1.07 mmol)의 Pd2(dba)3, 0.72 g(3.57 mmol)의 P(t-bu)3, 8.59 g(89.36 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 10.44 g (yield: 72 %)을 획득하였다.Pd 2 (dba) 3 and 0.72 g (3.57 mmol) of Pd 2 (dib) 3, 0.98 g (1.07 mmol) of 1-bromonaphthalene and 13.55 g (35.74 mmol) of the compound synthesized in Preparation Example 2, (t-bu) 3, 8.59 g (89.36 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 10.44 g (yield: 72%) of the desired compound was obtained by column chromatography.
GC-Mass (이론치: 405.92 g/mol, 측정치: 405 g/mol)GC-Mass (theory: 405.92 g / mol, measured: 405 g / mol)
1H-NMR: δ 6.56 (d, 2H), 6.69 (d, 2H), 7.00 (d, 1H), 7.24 (d, 2H), 7.50 (m, 11H), 8.00 (m, 2H)
2H), 7.50 (m, 11H), 8.00 (m, 2H), 7.24 (d,
[준비예 7] [Preparation Example 7] N-([1,1'-biphenyl]-4-yl)-N-(4-chlorophenyl)naphthalen-2-amine의 합성Synthesis of N - ([1,1'-biphenyl] -4-yl) -N- (4-chlorophenyl) naphthalen-2-amine
질소 기류 하에서 준비예 2 에서 합성된 화합물 10.0 g (35.74 mmol), 13.55 g(35.74 mmol)의 2-bromonaphthalene, 0.98 g(1.07 mmol)의 Pd2(dba)3, 0.72 g(3.57 mmol)의 P(t-bu)3, 8.59 g(89.36 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 10.00 g (yield: 69 %)을 획득하였다.Pd 2 (dba) 3 and 0.72 g (3.57 mmol) of Pd 2 (dib) 3, 0.98 g (1.07 mmol) of 2-bromonaphthalene and 13.55 g (35.74 mmol) of the compound synthesized in Preparation Example 2, (t-bu) 3, 8.59 g (89.36 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 10.00 g (yield: 69%) of the desired compound was obtained by column chromatography.
GC-Mass (이론치: 405.92 g/mol, 측정치: 405 g/mol)GC-Mass (theory: 405.92 g / mol, measured: 405 g / mol)
1H-NMR: δ 6.57 (d, 2H), 6.69 (d, 2H), 7.05 (d, 1H), 7.24 (d, 2H), 7.60 (m, 11H), 8.00 (m, 2H)
2H), 7.60 (d, 2H), 6.69 (d, 2H), 7.05 (d,
[준비예 8] [Preparation Example 8] N-([1,1'-biphenyl]-4-yl)-N-(4-chlorophenyl)dibenzo[b,d]furan-2-amine의 합성Synthesis of N - ([1,1'-biphenyl] -4-yl) -N- (4-chlorophenyl) dibenzo [b, d] furan-
질소 기류 하에서 준비예 2 에서 합성된 화합물 10.0 g (35.74 mmol), 8.83 g(35.74 mmol)의 2-bromodibenzo[b,d]furan, 0.98 g(1.07 mmol)의 Pd2(dba)3, 0.72 g(3.57 mmol)의 P(t-bu)3, 8.59 g(89.36 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 10.36 g (yield: 65 %)을 획득하였다.The synthesized compound in Preparation Example 2 was conducted in a nitrogen atmosphere 10.0 g (35.74 mmol), 8.83 g (35.74 mmol) 2-bromodibenzo [b, d] furan, 0.98 g Pd 2 (dba) of (1.07 mmol) 3, 0.72 g of (3.57 mmol) of P (t-bu) 3, 8.59 g (89.36 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 10.36 g (yield: 65%) of the desired compound was obtained by column chromatography.
GC-Mass (이론치: 445.94 g/mol, 측정치: 445 g/mol)GC-Mass (calculated: 445.94 g / mol, measured: 445 g / mol)
1H-NMR: δ 6.30 (d, 1H), 6.69 (d, 2H), 7.05 (d, 1H), 7.54 (m, 12H), 7.50 (m, 7H), 7.62 (m, 2H), 7.85 (d, 1H)
7H), 7.62 (m, 2H), 7.85 (d, IH), 7.54 (d, IH) , 1H)
[준비예 9] [Preparation Example 9] N-(4-chlorophenyl)-N-(4-(dibenzo[b,d]furan-4-yl)phenyl)-[1,1'-biphenyl]-4-amine의 합성Synthesis of N- (4-chlorophenyl) -N- (4- (dibenzo [b, d] furan-4-yl) phenyl) - [1,1'-biphenyl]
질소 기류 하에서 준비예 2 에서 합성된 화합물 10.0 g (35.74 mmol), 11.55 g(35.74 mmol)의 4-(4-bromophenyl)dibenzo[b,d]furan, 0.98 g(1.07 mmol)의 Pd2(dba)3, 0.72 g(3.57 mmol)의 P(t-bu)3, 8.59 g(89.36 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 14.36 g (yield: 77 %)을 획득하였다.A mixture of 10.0 g (35.74 mmol) of the compound synthesized in Preparation Example 2 and 11.55 g (35.74 mmol) of 4- (4-bromophenyl) dibenzo [b, d] furan and 0.98 g (1.07 mmol) of Pd 2 ) 3, 0.72 g (3.57 mmol) of P (t-bu) 3, 8.59 g (89.36 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 14.36 g (yield: 77%) of the desired compound was obtained by column chromatography.
GC-Mass (이론치: 522.03 g/mol, 측정치: 522 g/mol)GC-Mass (calculated: 522.03 g / mol, measured: 522 g / mol)
1H-NMR: δ 6.52 (d, 2H), 6.70 (d, 4H), 7.38 (m, 14H), 7.65 (d, 1H), 7.80 (m, 3H),
(D, 2H), 6.70 (d, 2H), 7.80 (d, 2H)
[준비예 10] [Preparation Example 10] N-([1,1'-biphenyl]-4-yl)-N-(4-chlorophenyl)dibenzo[b,d]thiophen-2-amine의 합성Synthesis of N - ([1,1'-biphenyl] -4-yl) -N- (4-chlorophenyl) dibenzo [b, d] thiophen-2-amine
질소 기류 하에서 준비예 2 에서 합성된 화합물 10.0 g (35.74 mmol), 13.55 g(35.74 mmol)의 2-bromodibenzo[b,d]thiophene, 0.98 g(1.07 mmol)의 Pd2(dba)3, 0.72 g(3.57 mmol)의 P(t-bu)3, 8.59 g(89.36 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 16.20 g (yield: 70 %)을 획득하였다. The synthesized compound in Preparation Example 2 was conducted in a nitrogen atmosphere 10.0 g (35.74 mmol), 13.55 g 2-bromodibenzo of (35.74 mmol) [b, d ] thiophene, 0.98 g Pd 2 (dba) of (1.07 mmol) 3, 0.72 g (3.57 mmol) of P (t-bu) 3, 8.59 g (89.36 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 16.20 g (yield: 70%) of the target compound was obtained by column chromatography.
GC-Mass (이론치: 462.00 g/mol, 측정치: 462 g/mol)GC-Mass (calculated: 462.00 g / mol, measured: 462 g / mol)
1H-NMR: δ 6.30 (d, 1H), 6.69 (d, 2H), 7.05 (d, 1H), 7.54 (m, 12H), 7.50 (m, 7H), 7.62 (m, 2H), 7.85 (d, 1H)
7H), 7.62 (m, 2H), 7.85 (d, IH), 7.54 (d, IH) , 1H)
[준비예 11] [Preparation Example 11] N-([1,1'-biphenyl]-4-yl)-N-(4-chlorophenyl)-9,9-dimethyl-9H-fluoren-2-amine의 합성Synthesis of N - ([1,1'-biphenyl] -4-yl) -N- (4-chlorophenyl) -9,9-dimethyl-9H-fluoren-
질소 기류 하에서 준비예 2 에서 합성된 화합물 10.0 g (35.74 mmol), 9.76 g(35.74 mmol)의 2-bromo-9,9-dimethyl-9H-fluorene, 0.98 g(1.07 mmol)의 Pd2(dba)3, 0.72 g(3.57 mmol)의 P(t-bu)3, 8.59 g(89.36 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 12.65 g (yield: 75 %)을 획득하였다. 10.0 g (35.74 mmol) of the compound synthesized in Preparation Example 2, 9.76 g (35.74 mmol) of 2-bromo-9,9-dimethyl-9H-fluorene and 0.98 g (1.07 mmol) of Pd 2 3, 0.72 g (3.57 mmol) of P (t-bu) 3, 8.59 g (89.36 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 12.65 g (yield: 75%) of the target compound was obtained by column chromatography.
GC-Mass (이론치: 472.02 g/mol, 측정치: 472 g/mol)GC-Mass (calculated: 472.02 g / mol, measured: 472 g / mol)
1H-NMR: δ 1.70 (s, 6H), 6.39 (m, 3H), 6.42 (m, 3H), 7.24 (m, 3H), 7.50 (m, 2H), 7.62 (m, 8H), 7.85 (d, 1H)
(M, 3H), 7.24 (m, 3H), 7.50 (m, 2H), 7.62 (m, 8H), 7.85 , 1H)
[준비예 12] [Preparation Example 12] N-([1,1'-biphenyl]-4-yl)-4'-chloro-[1,1'-biphenyl]-4-amine의 합성Synthesis of N - ([1,1'-biphenyl] -4-yl) -4'-chloro- [1,1'-biphenyl] -4-amine
질소 기류 하에서 40.0 g(179.29 mmol)의 4,4'-dichloro-1,1'-biphenyl, 30.34 g(179.29 mmol)의 [1,1'-biphenyl]-4-amine, 4.93 g(5.38 mmol)의 Pd2(dba)3, 3.63 g(17.93 mmol)의 P(t-bu)3, 43.07 g(448.23 mmol)의 NaO(t-bu) 및 toluene (1000 ml)를 혼합하고 110℃에서 5시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 40.83 g (yield: 64 %)을 획득하였다. 4'-dichloro-1,1'-biphenyl, 30.34 g (179.29 mmol) of [1,1'-biphenyl] -4-amine and 4.93 g (5.38 mmol) of 40.0 g (179.29 mmol) Of Pd 2 (dba) 3, 3.63 g (17.93 mmol) of P (t-bu) 3, 43.07 g (448.23 mmol) of NaO (t-bu) and toluene (1000 ml) Lt; / RTI > After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 40.83 g (yield: 64%) of the target compound was obtained by column chromatography.
GC-Mass (이론치: 355.86 g/mol, 측정치: 355 g/mol)GC-Mass (355.86 g / mol, measured: 355 g / mol)
1H-NMR: δ 4.01 (s, 1H), 6.70 (d, 4H), 7.40 (t, 1H), 7.54 (m, 10H), 8.12 (d, 2H)
1H), 7.40 (t, 1H), 7.54 (m, 10H), 8.12 (d, 2H)
[준비예 13] [Preparation Example 13] N-([1,1'-biphenyl]-4-yl)-N-(4-chlorophenyl)-9,9-dimethyl-9H-fluoren-2-amine의 합성Synthesis of N - ([1,1'-biphenyl] -4-yl) -N- (4-chlorophenyl) -9,9-dimethyl-9H-fluoren-
질소 기류 하에서 준비예 12 에서 합성된 화합물 10.0 g (28.10 mmol), 7.23 g(28.10 mmol)의 2-bromophenanthrene, 0.77 g(0.84 mmol)의 Pd2(dba)3, 0.57 g(2.81 mmol)의 P(t-bu)3, 6.75 g(70.25 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 12.55 g (yield: 84 %)을 획득하였다. To a solution of 10.0 g (28.10 mmol) of the compound prepared in Preparation Example 12, 7.23 g (28.10 mmol) of 2-bromophenanthrene, 0.77 g (0.84 mmol) of Pd 2 (dba) 3 and 0.57 g (2.81 mmol) of P (t-bu) 3, 6.75 g (70.25 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 12.55 g (yield: 84%) of the target compound was obtained by column chromatography.
GC-Mass (이론치: 532.07 g/mol, 측정치: 532 g/mol)GC-Mass (calculated: 532.07 g / mol, measured: 532 g / mol)
1H-NMR: δ 6.70 (d, 4H), 7.10 (d, 1H), 7.37 (d, 1H), 7.45 (m, 10H), 7.71 (d, 2H), 8.80 (m, 2H), 8.20 (m, 3H), 8.90 (d, 1H), 8.95 (d, 1H)
(M, 2H), 8.80 (m, 2H), 8.20 (m, 2H), 7.47 , 3H), 8.90 (d, 1 H), 8.95 (d, 1 H)
[준비예 14] [Preparation Example 14] N-([1,1'-biphenyl]-4-yl)-N-(4'-chloro-[1,1'-biphenyl]-4-yl)phenanthren-9-amine의 합성Synthesis of N - ([1,1'-biphenyl] -4-yl) -N- (4'-chloro- [1,1'-biphenyl] -4-yl) phenanthren-
질소 기류 하에서 준비예 12 에서 합성된 화합물 10.0 g (28.10 mmol), 7.23 g(28.10 mmol)의 9-bromophenanthrene, 0.77 g(0.84 mmol)의 Pd2(dba)3, 0.57 g(2.81 mmol)의 P(t-bu)3, 6.75 g(70.25 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 12.00 g (yield: 80 %)을 획득하였다. A mixture of 10.0 g (28.10 mmol) of the compound prepared in Preparation Example 12, 7.23 g (28.10 mmol) of 9-bromophenanthrene, 0.77 g (0.84 mmol) of Pd 2 (dba) 3 and 0.57 g (2.81 mmol) of P (t-bu) 3, 6.75 g (70.25 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 12.00 g (yield: 80%) of the desired compound was obtained by column chromatography.
GC-Mass (이론치: 532.07 g/mol, 측정치: 532 g/mol)GC-Mass (calculated: 532.07 g / mol, measured: 532 g / mol)
1H-NMR: δ 6.70 (d, 4H), 7.15 (d, 1H), 7.40 (d, 1H), 7.50 (m, 10H), 7.71 (d, 2H), 8.80 (m, 2H), 8.20 (m, 3H) , 8.90 (d, 1H) , 8.95 (d, 1H)
(D, 2H), 8.80 (m, 2H), 8.20 (m, 2H), 7.80 , 3H), 8.90 (d, 1 H), 8.95 (d, 1 H)
[준비예 15] [Preparation Example 15] N-([1,1'-biphenyl]-4-yl)-N-(4'-chloro-[1,1'-biphenyl]-4-yl)phenanthren-9-amine의 합성Synthesis of N - ([1,1'-biphenyl] -4-yl) -N- (4'-chloro- [1,1'-biphenyl] -4-yl) phenanthren-
질소 기류 하에서 준비예 12 에서 합성된 화합물 10.0 g (28.10 mmol), 8.63 g(28.10 mmol)의 2-bromotriphenylene, 0.77 g(0.84 mmol)의 Pd2(dba)3, 0.57 g(2.81 mmol)의 P(t-bu)3, 6.75 g(70.25 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 12.43 g (yield: 76 %)을 획득하였다. 2-bromotriphenylene, 0.77 g (0.84 mmol) of Pd 2 (dba) 3 and 0.57 g (2.81 mmol) of the compound synthesized in Preparation Example 12, 10.0 g (28.10 mmol) (t-bu) 3, 6.75 g (70.25 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 12.43 g (yield: 76%) of the desired compound was obtained by column chromatography.
GC-Mass (이론치: 582.13 g/mol, 측정치: 582 g/mol)GC-Mass (calculated: 582.13 g / mol, measured: 582 g / mol)
1H-NMR: δ 6.50 (m, 4H), 7.05 (d, 1H), 7.57 (m, 11H), 7.80 (m, 5H), 8.30 (m, 5H), 8.60 (d, 1H)
1H), 7.80 (m, 5H), 8.30 (m, 5H), 8.60 (d,
[준비예 16] [Preparation Example 16] N-([1,1'-biphenyl]-4-yl)-N-(4'-chloro-[1,1'-biphenyl]-4-yl)naphthalen-1-amine의 합성Synthesis of N - ([1,1'-biphenyl] -4-yl) -N- (4'-chloro- [1,1'-biphenyl] -4-yl) naphthalen-
질소 기류 하에서 준비예 12 에서 합성된 화합물 10.0 g (28.10 mmol), 5.82 g(28.10 mmol)의 1-bromonaphthalene, 0.77 g(0.84 mmol)의 Pd2(dba)3, 0.57 g(2.81 mmol)의 P(t-bu)3, 6.75 g(70.25 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 10.97 g (yield: 81 %)을 획득하였다. 1-bromonaphthalene, 0.77 g (0.84 mmol) of Pd 2 (dba) 3 and 0.57 g (2.81 mmol) of the compound synthesized in Preparation Example 12, 10.0 g (28.10 mmol) (t-bu) 3, 6.75 g (70.25 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 10.97 g (yield: 81%) of the desired compound was obtained by column chromatography.
GC-Mass (이론치: 482.01 g/mol, 측정치: 482 g/mol)GC-Mass (calculated: 482.01 g / mol, measured: 482 g / mol)
1H-NMR: δ 6.50 (m, 4H), 7.90 (d, 1H), 7.34 (m, 2H), 7.55 (m, 13H), 8.03 (m, 4H)
7.45 (m, 2H), 7.55 (m, 13H), 8.03 (m, 4H)
[준비예 17] [Preparation Example 17] N-([1,1'-biphenyl]-4-yl)-N-(4'-chloro-[1,1'-biphenyl]-4-yl)dibenzo[b,d]furan-2-amine의 합성Biphenyl] -4-yl) -N- (4'-chloro- [1,1'-biphenyl] -4-yl) dibenzo [b, d] furan- synthesis
질소 기류 하에서 준비예 12 에서 합성된 화합물 10.0 g (28.10 mmol), 6.94 g(28.10 mmol)의 2-bromodibenzo[b,d]furan, 0.77 g(0.84 mmol)의 Pd2(dba)3, 0.57 g(2.81 mmol)의 P(t-bu)3, 6.75 g(70.25 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 9.24 g (yield: 63 %)을 획득하였다. The synthesized compound from Preparation Example 12 was conducted in a nitrogen atmosphere 10.0 g (28.10 mmol), 6.94 g (28.10 mmol) 2-bromodibenzo [b, d] furan, 0.77 g Pd 2 (dba) of (0.84 mmol) 3, 0.57 g of (2.81 mmol) of P (t-bu) 3, 6.75 g (70.25 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 9.24 g (yield: 63%) of the target compound was obtained by column chromatography.
GC-Mass (이론치: 522.03 g/mol, 측정치: 522 g/mol)GC-Mass (calculated: 522.03 g / mol, measured: 522 g / mol)
1H-NMR: δ 6.35 (d, 1H), 6.54 (d, 4H), 7.55 (m, 14H), 7.70 (m, 2H), 8.85 (d, 1H), 8.15 (d, 2H)
2H), 8.85 (d, IH), 8.15 (d, 2H), 7.50 (d, IH)
[준비예 18] [Preparation Example 18] N-([1,1'-biphenyl]-4-yl)-N-(4'-chloro-[1,1'-biphenyl]-4-yl)dibenzo[b,d]thiophen-2-amine의 합성Biphenyl-4-yl) -N- (4'-chloro- [1,1'-biphenyl] -4-yl) dibenzo [b, d] thiophen-2-amine synthesis
질소 기류 하에서 준비예 12 에서 합성된 화합물 10.0 g (28.10 mmol), 7.39 g(28.10 mmol)의 2-bromodibenzo[b,d]thiophene, 0.77 g(0.84 mmol)의 Pd2(dba)3, 0.57 g(2.81 mmol)의 P(t-bu)3, 6.75 g(70.25 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 8.31 g (yield: 55 %)을 획득하였다. The synthesized compound from Preparation Example 12 was conducted in a nitrogen atmosphere 10.0 g (28.10 mmol), 7.39 g (28.10 mmol) 2-bromodibenzo [b, d] thiophene, 0.77 g Pd 2 (dba) of (0.84 mmol) 3, 0.57 g of (2.81 mmol) of P (t-bu) 3, 6.75 g (70.25 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 8.31 g (yield: 55%) of the target compound was obtained by column chromatography.
GC-Mass (이론치: 538.10 g/mol, 측정치: 538 g/mol)GC-Mass (calculated: 538.10 g / mol, measured: 538 g / mol)
1H-NMR: δ 6.32 (d, 1H), 6.54 (d, 4H), 7.55 (m, 14H), 7.70 (m, 2H), 8.85 (d, 1H), 8.15 (d, 2H)
2H), 8.85 (d, IH), 8.15 (d, 2H), 7.30 (d, IH)
[준비예 19] [Preparation Example 19] N-(4'-(9H-carbazol-9-yl)-[1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine의 합성Synthesis of N- (4 '- (9H-carbazol-9-yl) - [1,1'-biphenyl] -4-yl) -9,9-dimethyl-9H-fluoren-
질소 기류 하에서 20.0 g(50.21 mmol)의 9-(4'-bromo-[1,1'-biphenyl]-4-yl)-9H-carbazole, 10.51 g(50.21 mmol)의 9,9-dimethyl-9H-fluoren-2-amine, 1.38 g(1.51 mmol)의 Pd2(dba)3, 1.02 g(5.02 mmol)의 P(t-bu)3, 12.06 g(125.54 mmol)의 NaO(t-bu) 및 toluene (300 ml)를 혼합하고 110℃에서 5시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 12.06 g (yield: 52 %)을 획득하였다. (10.21 g, 50.21 mmol) of 9,9-dimethyl-9H-carbazole was added to a solution of 20.0 g (50.21 mmol) of 9- -fluoren-2-amine, 1.38 g (1.51 mmol) Pd 2 (dba) NaO (t-bu) of 3, 1.02 g (5.02 mmol) P (t-bu) 3, 12.06 g (125.54 mmol) of, and the toluene (300 ml) were mixed and stirred at 110 ° C for 5 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 12.06 g (yield: 52%) of the target compound was obtained by column chromatography.
GC-Mass (이론치: 526.67 g/mol, 측정치: 526 g/mol)GC-Mass (calculated: 526.67 g / mol, measured: 526 g / mol)
1H-NMR: δ 1.70 (s, 6H), 4.01 (s, 1H), 6.50 (d, 1H), 6.90 (m, 3H), 7.30 (m, 5H), 7.50 (m, 8H), 7.30 (d, 2H), 7.94 (m, 2H), 8.12 (d, 1H) , 8.55 (d, 1H)
(M, 2H), 7.50 (m, 8H), 7.30 (d, 1H), 6.90 2H), 7.94 (m, 2H), 8.12 (d, 1H), 8.55
[준비예 20] [Preparation Example 20] N1-(9,9-dimethyl-9H-fluoren-2-yl)-N1,N4-diphenylbenzene-1,4-diamine의 합성Synthesis of N1- (9,9-dimethyl-9H-fluoren-2-yl) -N1, N4-diphenylbenzene-1,4-diamine
질소 기류 하에서 20.0 g(76.83 mmol)의 N1,N4-diphenylbenzene-1,4-diamine, 20.99 g(76.83 mmol)의 2-bromo-9,9-dimethyl-9H-fluorene, 2.11 g(2.30 mmol)의 Pd2(dba)3, 1.56 g(7.68 mmol)의 P(t-bu)3, 18.46 g(192.06 mmol)의 NaO(t-bu) 및 toluene (400 ml)를 혼합하고 110℃에서 5시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 15.64 g (yield: 45 %)을 획득하였다. A solution of 20.0 g (76.83 mmol) of N1, N4-diphenylbenzene-1,4-diamine, 20.99 g (76.83 mmol) 2-bromo-9,9-dimethyl-9H- fluorene and 2.11 g (2.30 mmol) mixture of Pd 2 (dba) 3, 1.56 g (7.68 mmol) of P (t-bu) 3, 18.46 g NaO (t-bu) , and toluene (400 ml) of (192.06 mmol), and for 5 hours at 110 ℃ Lt; / RTI > After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 15.64 g (yield: 45%) of the title compound was obtained by column chromatography.
GC-Mass (이론치: 452.59 g/mol, 측정치: 452 g/mol)GC-Mass (theory: 452.59 g / mol, measured: 452 g / mol)
1H-NMR: δ 1.70 (s, 6H), 4.01 (s, 1H), 6.35 (d, 4H), 6.60 (m, 3H), 6.80 (m, 3H), 7.20 (m, 7H) , 7.30 (d, 1H), 7.61 (d, 1H), 7.70 (d, 1H)
(M, 3H), 7.20 (m, 7H), 7.30 (d, 4H), 6.60 , 7.61 (d, 1 H), 7.70 (d, 1 H)
[준비예 21] [Preparation Example 21] N1-(9,9-dimethyl-9H-fluoren-2-yl)-N1,N4-di-p-tolylbenzene-1,4-diamine의 합성Synthesis of N1- (9,9-dimethyl-9H-fluoren-2-yl) -N1, N4-di-p-tolylbenzene-1,4-
질소 기류 하에서 20.0 g(69.35 mmol)의 N1,N4-di-p-tolylbenzene-1,4-diamine, 18.94 g(69.35 mmol)의 2-bromo-9,9-dimethyl-9H-fluorene, 1.91 g(2.08 mmol)의 Pd2(dba)3, 1.40 g(6.94 mmol)의 P(t-bu)3, 16.66 g(173.38. mmol)의 NaO(t-bu) 및 toluene (400 ml)를 혼합하고 110℃에서 5시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 15 g (yield: 54 %)을 획득하였다. N, di-p-tolylbenzene-1,4-diamine, 18.94 g (69.35 mmol) of 2-bromo-9,9-dimethyl-9H-fluorene, 1.91 g (69.35 mmol) 2.08 mmol) Pd 2 (dba) 3, 1.40 g (P (t-bu) of a 6.94 mmol) of 3, 16.66 g (173.38. mmol ) of NaO (t-bu), and toluene (400 ml) mixture and 110 the Lt; 0 > C for 5 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 15 g of the target compound (yield: 54%) was obtained by column chromatography.
GC-Mass (이론치: 480.64 g/mol, 측정치: 480 g/mol)GC-Mass (theory: 480.64 g / mol, measurement: 480 g / mol)
1H-NMR: δ 1.70 (s, 6H), 2.30 (s, 6H), 4.01 (s, 1H), 6.35 (d, 4H), 6.60 (m, 3H), 6.80 (m, 3H), 7.20 (m, 7H) , 7.30 (d, 1H), 7.61 (d, 1H), 7.70 (d, 1H)
(M, 3H), 6.80 (m, 3H), 7.20 (m, 2H), 6.30 , 7H), 7.30 (d, IH), 7.61 (d, IH), 7.70
[준비예 22] [Preparation Example 22] N1-(9,9-dimethyl-9H-fluoren-2-yl)-N1,N4-di(naphthalen-1-yl)benzene-1,4-diamine의 합성Synthesis of N1- (9,9-dimethyl-9H-fluoren-2-yl) -N1, N4-di (naphthalen-
질소 기류 하에서 20.0 g(55.49 mmol)의 N1,N4-di(naphthalen-1-yl)benzene-1,4-diamine, 15.16 g(55.49 mmol)의 2-bromo-9,9-dimethyl-9H-fluorene, 1.52 g(1.66 mmol)의 Pd2(dba)3, 1.12 g(5.55 mmol)의 P(t-bu)3, 13.33 g(138.72 mmol)의 NaO(t-bu) 및 toluene (400 ml)를 혼합하고 110℃에서 5시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 17.78 g (yield: 58 %)을 획득하였다. N-di (naphthalen-1-yl) benzene-1,4-diamine and 15.16 g (55.49 mmol) of 2-bromo-9,9-dimethyl-9H-fluorene , the 1.52 g (1.66 mmol) Pd 2 (dba) 3, 1.12 g P (t-bu) 3, 13.33 g NaO (t-bu) , and toluene (400 ml) of (138.72 mmol) of (5.55 mmol) of And the mixture was stirred at 110 DEG C for 5 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 17.78 g (yield: 58%) of the desired compound was obtained by column chromatography.
GC-Mass (이론치: 552.71 g/mol, 측정치: 552 g/mol)GC-Mass (calculated: 552.71 g / mol, measured: 552 g / mol)
1H-NMR: δ 1.70 (s, 6H), 4.01 (s, 1H), 6.35 (d, 4H), 6.55 (d, 1H), 6.80 (d, 1H), 7.05 (d, 2H), 7.36 (m, 4H), 7.61 (m, 8H), 7.75 (m, 5H)
(D, 1H), 7.05 (d, 2H), 7.36 (d, 1H), 6.40 , 4H), 7.61 (m, 8H), 7.75 (m, 5H)
[준비예 23] [Preparation Example 23] N1-(9,9-dimethyl-9H-fluoren-2-yl)-N1,N4-di(naphthalen-1-yl)benzene-1,4-diamine의 합성Synthesis of N1- (9,9-dimethyl-9H-fluoren-2-yl) -N1, N4-di (naphthalen-
질소 기류 하에서 20.0 g(48.48 mmol)의 N1,N4-di(naphthalen-1-yl)benzene-1,4-diamine, 13.24 g(48.48 mmol)의 2-bromo-9,9-dimethyl-9H-fluorene, 1.33 g(1.45 mmol)의 Pd2(dba)3, 0.98 g(4.85 mmol)의 P(t-bu)3, 11.65 g(121.21 mmol)의 NaO(t-bu) 및 toluene (400 ml)를 혼합하고 110℃에서 5시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 18.17 g (yield: 62 %)을 획득하였다. N-di (naphthalen-1-yl) benzene-1,4-diamine and 13.24 g (48.48 mmol) of 2-bromo-9,9-dimethyl-9H-fluorene , the 1.33 g 3, Pd 2 (dba ) of (1.45 mmol) 0.98 g P ( t-bu) 3, 11.65 g NaO (t-bu) , and toluene (400 ml) of (121.21 mmol) of (4.85 mmol) And the mixture was stirred at 110 DEG C for 5 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 18.17 g (yield: 62%) of the target compound was obtained by column chromatography.
GC-Mass (이론치: 604.78 g/mol, 측정치: 604 g/mol)GC-Mass (theory: 604.78 g / mol, measurement: 604 g / mol)
1H-NMR: δ 1.70 (s, 6H), 4.01 (s, 1H), 6.35 (d, 4H), 6.70 (m, 6H), 7.40 (m, 17H), 7.60 (d, 1H), 7.87 (d, 1H)
(D, 1H), 7.87 (d, IH), 7.70 (d, IH) , 1H)
[준비예 24] [Preparation Example 24] N4-(9,9-dimethyl-9H-fluoren-2-yl)-N4,N4'-diphenyl-[1,1'-biphenyl]-4,4'-diamine의 합성Synthesis of N4- (9,9-dimethyl-9H-fluoren-2-yl) -N4, N4'-diphenyl- [1,1'-biphenyl] -4,4'-diamine
질소 기류 하에서 20.0 g(59.45 mmol)의 N4,N4'-diphenyl-[1,1'-biphenyl]-4,4'-diamine, 16.24 g(59.45 mmol)의 2-bromo-9,9-dimethyl-9H-fluorene, 1.63 g(1.78 mmol)의 Pd2(dba)3, 1.20 g(5.94 mmol)의 P(t-bu)3, 14.28 g(148.62 mmol)의 NaO(t-bu) 및 toluene (400 ml)를 혼합하고 110℃에서 5시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 19.49 g (yield: 62 %)을 획득하였다. N, N4'-diphenyl- [1,1'-biphenyl] -4,4'-diamine and 16.24 g (59.45 mmol) of 2-bromo-9,9-dimethyl- 9H-fluorene, 1.63 g Pd 2 (dba) of (1.78 mmol) 3, 1.20 g (5.94 mmol) of P (t-bu) 3, 14.28 g NaO (t-bu) , and toluene (400 of (148.62 mmol) ml) were mixed and stirred at 110 ° C for 5 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 19.49 g (yield: 62%) of the target compound was obtained by column chromatography.
GC-Mass (이론치: 528.68 g/mol, 측정치: 528 g/mol)GC-Mass (calculated: 528.68 g / mol, measured: 528 g / mol)
1H-NMR: δ 1.70 (s, 6H), 4.01 (s, 1H), 6.80 (m, 10H), 7.20 (m, 7H), 7.40 (d, 1H), 7.60 (m, 6H) , 7.85 (d, 1H)
(D, IH), 7.60 (m, 6H), 7.85 (d, IH), 7.80 , 1H)
[준비예 25] [Preparation Example 25] N4-(9,9-dimethyl-9H-fluoren-2-yl)-N4,N4'-di-p-tolyl-[1,1'-biphenyl]-4,4'-diamine의 합성Synthesis of N4- (9,9-dimethyl-9H-fluoren-2-yl) -N4, N4'-di-p-tolyl- [1,1'-biphenyl] -4,4'-diamine
질소 기류 하에서 20.0 g(54.87 mmol)의 N4,N4'-di-p-tolyl-[1,1'-biphenyl]-4,4'-diamine, 14.99 g(54.87 mmol)의 2-bromo-9,9-dimethyl-9H-fluorene, 1.51 g(1.65 mmol)의 Pd2(dba)3, 1.11 g(5.49 mmol)의 P(t-bu)3, 13.18 g(137.18 mmol)의 NaO(t-bu) 및 toluene (400 ml)를 혼합하고 110℃에서 5시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 16.80 g (yield: 55 %)을 획득하였다. N4'-di-p-tolyl- [1,1'-biphenyl] -4,4'-diamine, 14.99 g (54.87 mmol) of 2-bromo-9, 9-dimethyl-9H-fluorene, 1.51 g (1.65 mmol) Pd 2 (dba) 3, 1.11 g (5.49 mmol) of P (t-bu) 3, 13.18 g (137.18 mmol) NaO (t-bu) of And toluene (400 ml) were mixed and stirred at 110 ° C for 5 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 16.80 g (yield: 55%) of the desired compound was obtained by column chromatography.
GC-Mass (이론치: 556.74 g/mol, 측정치: 556 g/mol)GC-Mass (calculated: 556.74 g / mol, measured: 556 g / mol)
1H-NMR: δ 1.70 (s, 6H), 2.35 (s, 6H), 4.01 (s, 1H), 6.50 (m, 3H), 6.90 (m, 5H), 7.00 (d, 2H), 7.30 (m, 6H) , 7.85 (m, 6H) , 7.90 (d, 1H)
(M, 3H), 6.90 (m, 5H), 7.00 (d, 2H), 7.30 (m, 2H) , 6H), 7.85 (m, 6H), 7.90 (d, IH)
[준비예 26] [Preparation Example 26] N4-(9,9-dimethyl-9H-fluoren-2-yl)-N4,N4'-di(naphthalen-1-yl)-[1,1'-biphenyl]-4,4'-diamine의 합성Synthesis of N4- (9,9-dimethyl-9H-fluoren-2-yl) -N4, N4'-di (naphthalen-1-yl) - [1,1'-biphenyl] -4,4'-
질소 기류 하에서 20.0 g(45.81 mmol)의 N4,N4'-di(naphthalen-1-yl)-[1,1'-biphenyl]-4,4'-diamine, 14.99 g(45.81 mmol)의 2-bromo-9,9-dimethyl-9H-fluorene, 1.26 g(1.37 mmol)의 Pd2(dba)3, 0.93 g(4.58 mmol)의 P(t-bu)3, 11.01 g(114.53 mmol)의 NaO(t-bu) 및 toluene (400 ml)를 혼합하고 110℃에서 5시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 14.69 g (yield: 51 %)을 획득하였다. (45.81 mmol) of N4, N4'-di- (1,1'-biphenyl) -4,4'-diamine and 14.99 g (45.81 mmol) of 2-bromo -9,9-dimethyl-9H-fluorene, 1.26 g (1.37 mmol) Pd 2 (dba) 3, 0.93 g (4.58 mmol) P (t- bu) 3 and 11.01 g (114.53 mmol) NaO -bu) and toluene (400 ml) were mixed and stirred at 110 ° C for 5 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 14.69 g (yield: 51%) of the desired compound was obtained by column chromatography.
GC-Mass (이론치: 628.80 g/mol, 측정치: 628 g/mol)GC-Mass (theory: 628.80 g / mol, measurement: 628 g / mol)
1H-NMR: δ 1.70 (s, 6H), 4.01 (s, 1H), 6.90 (m, 5H), 7.00 (d, 2H), 7.30 (t, 1H), 7.40 (m, 3H) , 7.85 (m, 12H) , 8.02 (m, 5H)
7.30 (t, 1H), 7.40 (m, 3H), 7.85 (m, 2H), 7.90 , 12 H), 8.02 (m, 5 H)
[준비예 27] [Preparation Example 27] N4,N4'-di([1,1'-biphenyl]-4-yl)-N4-(9,9-dimethyl-9H-fluoren-2-yl)-[1,1'-biphenyl]-4,4'-diamine의 합성N4, N4'-di ([1,1'-biphenyl] -4-yl) -N4- (9,9-dimethyl-9H- fluoren- 2- yl) - [1,1'-biphenyl] Synthesis of 4'-diamine
질소 기류 하에서 20.0 g(40.93 mmol)의 N4,N4'-di([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine, 11.18 g(40.93 mmol)의 2-bromo-9,9-dimethyl-9H-fluorene, 1.12 g(1.23 mmol)의 Pd2(dba)3, 0.83 g(4.09 mmol)의 P(t-bu)3, 9.83 g(102.33 mmol)의 NaO(t-bu) 및 toluene (400 ml)를 혼합하고 110℃에서 5시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 18.67 g (yield: 67 %)을 획득하였다. Under a stream of nitrogen, 20.0 g (40.93 mmol) of N4, N4'-di ([1,1'-biphenyl] -4-yl) - [1,1'-biphenyl] -4,4'-diamine, 11.18 g 40.93 mmol) 2-bromo-9,9 -dimethyl-9H-fluorene, 1.12 g (1.23 mmol) of Pd 2 (dba) 3, 0.83 g (4.09 mmol) of P (t-bu) 3, 9.83 g of ( 102.33 mmol) of NaO (t-bu) and toluene (400 ml) were mixed and stirred at 110 ° C for 5 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 18.67 g (yield: 67%) of the target compound was obtained by column chromatography.
GC-Mass (이론치: 680.88 g/mol, 측정치: 680 g/mol)GC-Mass (calculated: 680.88 g / mol, measured: 680 g / mol)
1H-NMR: δ 1.70 (s, 6H), 4.01 (s, 1H), 6.70 (m, 10H), 7.50 (m, 4H), 7.50 (m, 18H), 7.90 (d, 1H)
1 H), 7.50 (m, 4H), 7.50 (m, 18H), 7.90 (d,
[준비예 28] [Preparation Example 28] N-(4-(9H-carbazol-9-yl)phenyl)-9,9-diphenyl-9H-fluoren-2-amine의 합성Synthesis of N- (4- (9H-carbazol-9-yl) phenyl) -9,9-diphenyl-9H-fluoren-
질소 기류 하에서 50.0 g(155.18 mmol)의 9-(4-bromophenyl)-9H-carbazole, 51.74 g(155.18 mmol)의 9,9-diphenyl-9H-fluoren-2-amine, 4.26 g(4.66 mmol)의 Pd2(dba)3, 3.14 g(15.52 mmol)의 P(t-bu)3, 37.28 g(387.96 mmol)의 NaO(t-bu) 및 toluene (1000 ml)를 혼합하고 110℃에서 5시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 72.24 g (yield: 81 %)을 획득하였다. 9.7 g (155.18 mmol) of 9,9-diphenyl-9H-fluoren-2-amine and 4.26 g (4.66 mmol) of 9- (4-bromophenyl) -9H- mixture of Pd 2 (dba) 3, NaO (t-bu) , and toluene (1000 ml) of P (t-bu) 3, 37.28 g (387.96 mmol) of 3.14 g (15.52 mmol), and for 5 hours at 110 ℃ Lt; / RTI > After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 72.24 g (yield: 81%) of the target compound was obtained by column chromatography.
GC-Mass (이론치: 574.71 g/mol, 측정치: 574 g/mol)GC-Mass (calculated: 574.71 g / mol, measured: 574 g / mol)
1H-NMR: δ 4.0 (s, 1H), 6.50 (m, 3H), 7.25 (m, 17H), 7.50 (m, 4H), 7.80 (m, 2H), 8.20 (d, 1H), 8.55 (d, 1H)
(D, 1H), 8.55 (m, 2H), 7.50 (m, 2H), 7.50 , 1H)
[준비예 29] [Preparation Example 29] N-(4-(9H-carbazol-9-yl)phenyl)-9,9'-spirobi[fluoren]-2-amine의 합성Synthesis of N- (4- (9H-carbazol-9-yl) phenyl) -9,9'-spirobi [fluoren] -2-amine
질소 기류 하에서 50.0 g(155.18 mmol)의 9-(4-bromophenyl)-9H-carbazole, 51.43 g(155.18 mmol)의 9,9'-spirobi[fluoren]-2-amine, 4.26 g(4.66 mmol)의 Pd2(dba)3, 3.14 g(15.52 mmol)의 P(t-bu)3, 37.28 g(387.96 mmol)의 NaO(t-bu) 및 toluene (1000 ml)를 혼합하고 110℃에서 5시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 66.66 g (yield: 75 %)을 획득하였다. (50.0 g, 155.18 mmol) of 9- (4-bromophenyl) -9H-carbazole, 51.43 g (155.18 mmol) of 9,9'-spirobi [fluoren] -2-amine, 4.26 g mixture of Pd 2 (dba) 3, NaO (t-bu) , and toluene (1000 ml) of P (t-bu) 3, 37.28 g (387.96 mmol) of 3.14 g (15.52 mmol), and for 5 hours at 110 ℃ Lt; / RTI > After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 66.66 g (yield: 75%) of the target compound was obtained by column chromatography.
GC-Mass (이론치: 572.70 g/mol, 측정치: 572 g/mol)GC-Mass (calculated: 572.70 g / mol, measured: 572 g / mol)
1H-NMR: δ 4.0 (s, 1H), 6.50 (m, 3H), 7.25 (m, 17H), 7.50 (m, 4H), 8.20 (d, 1H), 8.55 (d, 1H)
(D, IH), 7.50 (m, 4H), 7.50 (m, 4H)
[준비예 30] [Preparation Example 30] N1-(9,9-diphenyl-9H-fluoren-2-yl)-N1,N4-diphenylbenzene-1,4-diamine의 합성Synthesis of N1- (9,9-diphenyl-9H-fluoren-2-yl) -N1, N4-diphenylbenzene-1,4-diamine
질소 기류 하에서 10.0 g(25.17 mmol)의 2-bromo-9,9-diphenyl-9H-fluorene, 8.34 g(25.17 mmol)의 N1,N4-diphenylbenzene-1,4-diamine, 0.69 g(0.76 mmol)의 Pd2(dba)3, 0.51 g(2.52 mmol)의 P(t-bu)3, 6.05 g(62.92 mmol)의 NaO(t-bu) 및 toluene (150 ml)를 혼합하고 110℃에서 5시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 10.31 g (yield: 71 %)을 획득하였다. To a solution of 10.0 g (25.17 mmol) of 2-bromo-9,9-diphenyl-9H-fluorene, 8.34 g (25.17 mmol) of N1, N4- diphenylbenzene- 1,4-diamine and 0.69 g mixture of Pd 2 (dba) 3, 0.51 g (2.52 mmol) of P (t-bu) 3, 6.05 g NaO (t-bu) , and toluene (150 ml) of (62.92 mmol), and for 5 hours at 110 ℃ Lt; / RTI > After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 10.31 g (yield: 71%) of the target compound was obtained by column chromatography.
GC-Mass (이론치: 576.73 g/mol, 측정치: 576 g/mol)GC-Mass (calculated: 576.73 g / mol, measured: 576 g / mol)
1H-NMR: δ 4.0 (s, 1H), 6.40 (d, 4H), 6.70 (m, 3H), 7.00 (m, 3H), 8.80 (m, 17H), 7.90 (m, 2H), 8.00 (d, 1H)
7.80 (m, 2H), 8.00 (m, 2H), 7.90 (m, 2H) , 1H)
[준비예 31] [Preparation Example 31] N1-(9,9-diphenyl-9H-fluoren-2-yl)-N1,N4-di-p-tolylbenzene-1,4-diamine의 합성Synthesis of N1- (9,9-diphenyl-9H-fluoren-2-yl) -N1, N4-di-p-tolylbenzene-
질소 기류 하에서 10.0 g(25.17 mmol)의 2-bromo-9,9-diphenyl-9H-fluorene, 7.26 g(25.17 mmol)의 N1,N4-di-p-tolylbenzene-1,4-diamine, 0.69 g(0.76 mmol)의 Pd2(dba)3, 0.51 g(2.52 mmol)의 P(t-bu)3, 6.05 g(62.92 mmol)의 NaO(t-bu) 및 toluene (150 ml)를 혼합하고 110℃에서 5시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 11.42 g (yield: 75 %)을 획득하였다. N, N-di-p-tolylbenzene-1,4-diamine, 0.69 g (25.17 mmol) of 10.0 g (25.17 mmol) of 2-bromo-9,9- diphenyl-9H- Pd 2 (dba) a 0.76 mmol) 3, 0.51 g ( 2.52 mmol) of P (t-bu) 3, 6.05 g (62.92 mixture of NaO (t-bu), and toluene (150 ml) of mmol) and 110 ℃ Lt; / RTI > for 5 h. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 11.42 g (yield: 75%) of the desired compound was obtained by column chromatography.
GC-Mass (이론치: 604.78 g/mol, 측정치: 604 g/mol)GC-Mass (theory: 604.78 g / mol, measurement: 604 g / mol)
1H-NMR: δ 2.30 (s, 6H), 4.0 (s, 1H), 6.40 (d, 4H), 6.70 (m, 3H), 7.00 (m, 3H), 8.80 (m, 17H), 7.90 (m, 2H), 8.00 (d, 1H)
(M, 3H), 7.00 (m, 3H), 8.80 (m, 17H), 7.90 (m, , ≪ / RTI > 2H), 8.00 (d, 1H)
[준비예 32] [Preparation Example 32] N1-(9,9-diphenyl-9H-fluoren-2-yl)-N1,N4-di(naphthalen-1-yl)benzene-1,4-diamine의 합성Synthesis of N1- (9,9-diphenyl-9H-fluoren-2-yl) -N1, N4-di (naphthalen-1-yl) benzene-1,4-
질소 기류 하에서 10.0 g(25.17 mmol)의 2-bromo-9,9-diphenyl-9H-fluorene, 9.07 g(25.17 mmol)의 N1,N4-di(naphthalen-1-yl)benzene-1,4-diamine, 0.69 g(0.76 mmol)의 Pd2(dba)3, 0.51 g(2.52 mmol)의 P(t-bu)3, 6.05 g(62.92 mmol)의 NaO(t-bu) 및 toluene (150 ml)를 혼합하고 110℃에서 5시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 11.07 g (yield: 65 %)을 획득하였다. N, N4-di (naphthalen-1-yl) benzene-1,4-diamine (10.0 g, 25.17 mmol) was added dropwise to a solution of 9.07 g (25.17 mmol) of 2-bromo- , 0.69 g (0.76 mmol) Pd 2 (dba) 3, 0.51 g (2.52 mmol) P (t-bu) 3, 6.05 g NaO (t-bu) , and toluene (150 ml) of (62.92 mmol) of the And the mixture was stirred at 110 DEG C for 5 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 11.07 g (yield: 65%) of the desired compound was obtained by column chromatography.
GC-Mass (이론치: 676.84 g/mol, 측정치: 676 g/mol)GC-Mass (theory: 676.84 g / mol, measured: 676 g / mol)
1H-NMR: δ 4.0 (s, 1H), 6.40 (d, 4H), 6.70 (m, 3H), 7.00 (m, 5H), 8.80 (m, 17H), 7.90 (m, 2H), 8.00 (d, 1H)
(M, 2H), 8.00 (m, 2H), 7.90 (m, 2H), 7.40 , 1H)
[준비예 33] [Preparation Example 33] N4-(9,9-diphenyl-9H-fluoren-2-yl)-N4,N4'-diphenyl-[1,1'-biphenyl]-4,4'-diamine의 합성Synthesis of N4- (9,9-diphenyl-9H-fluoren-2-yl) -N4, N4'-diphenyl- [1,1'-biphenyl] -4,4'-diamine
질소 기류 하에서 10.0 g(25.17 mmol)의 2-bromo-9,9-diphenyl-9H-fluorene, 8.47 g(25.17 mmol)의 N4,N4'-diphenyl-[1,1'-biphenyl]-4,4'-diamine, 0.69 g(0.76 mmol)의 Pd2(dba)3, 0.51 g(2.52 mmol)의 P(t-bu)3, 6.05 g(62.92 mmol)의 NaO(t-bu) 및 toluene (150 ml)를 혼합하고 110℃에서 5시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 10.68 g (yield: 65 %)을 획득하였다. 10.0 g (25.17 mmol) of 2-bromo-9,9-diphenyl-9H-fluorene and 8.47 g (25.17 mmol) of N4, N4'- diphenyl- [1,1'-biphenyl] -4,4 '-diamine, 0.69 g Pd 2 ( dba) of (0.76 mmol) 3, 0.51 g (2.52 mmol) of P (t-bu) 3, 6.05 g NaO (t-bu) , and toluene (150 of (62.92 mmol) ml) were mixed and stirred at 110 ° C for 5 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 10.68 g (yield: 65%) of the desired compound was obtained by column chromatography.
GC-Mass (이론치: 652.82 g/mol, 측정치: 652 g/mol)GC-Mass (calculated: 652.82 g / mol, measured: 652 g / mol)
1H-NMR: δ 4.0 (s, 1H), 6.35 (d, 10H), 6.70 (m, 18H), 7.50 (m, 6H), 7.80 (d, 1H)
(M, 6H), 7.80 (d, IH), 7.70 (d, IH)
[준비예 34] [Preparation Example 34] N4-(9,9-diphenyl-9H-fluoren-2-yl)-N4,N4'-di-p-tolyl-[1,1'-biphenyl]-4,4'-diamine의 합성Synthesis of N4- (9,9-diphenyl-9H-fluoren-2-yl) -N4, N4'-di-p-tolyl- [1,1'-biphenyl] -4,4'-diamine
질소 기류 하에서 10.0 g(25.17 mmol)의 2-bromo-9,9-diphenyl-9H-fluorene, 8.92 g(25.17 mmol)의 N4,N4'-di-p-tolyl-[1,1'-biphenyl]-4,4'-diamine, 0.69 g(0.76 mmol)의 Pd2(dba)3, 0.51 g(2.52 mmol)의 P(t-bu)3, 6.05 g(62.92 mmol)의 NaO(t-bu) 및 toluene (150 ml)를 혼합하고 110℃에서 5시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 12.68 g (yield: 74 %)을 획득하였다. (10.1 g, 25.17 mmol) of 2-bromo-9,9-diphenyl-9H-fluorene and 8.92 g (25.17 mmol) of N4, N4'- di- p- tolyl- [1,1'- biphenyl] -4,4'-diamine, 0.69 g NaO ( t-bu) of (0.76 mmol) Pd 2 (dba ) 3, 0.51 g P (t-bu) 3, 6.05 g (62.92 mmol) of (2.52 mmol) of And toluene (150 ml) were mixed and stirred at 110 ° C for 5 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 12.68 g (yield: 74%) of the desired compound was obtained by column chromatography.
GC-Mass (이론치: 680.88 g/mol, 측정치: 680 g/mol)GC-Mass (calculated: 680.88 g / mol, measured: 680 g / mol)
1H-NMR: δ 2.30 (s, 6H), 4.0 (s, 1H), 6.35 (d, 10H), 6.70 (m, 18H), 7.50 (m, 6H), 7.80 (d, 1H)
(M, 6H), 7.80 (d, IH), 7.70 (d, IH)
[준비예 35] [Preparation Example 35] N1-(9,9'-spirobi[fluoren]-2-yl)-N1,N4-diphenylbenzene-1,4-diamine의 합성Synthesis of N1- (9,9'-spirobi [fluoren] -2-yl) -N1, N4-diphenylbenzene-1,4-diamine
질소 기류 하에서 10.0 g(25.17 mmol)의 2-bromo-9,9'-spirobi[fluorene], 8.92 g (25.17 mmol)의 N1,N4-diphenylbenzene-1,4-diamine, 0.69 g(0.76 mmol)의 Pd2(dba)3, 0.51 g(2.52 mmol)의 P(t-bu)3, 6.05 g(62.93 mmol)의 NaO(t-bu) 및 toluene (150 ml)를 혼합하고 110℃에서 5시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 10.27 g (yield: 71 %)을 획득하였다. N1-diphenylbenzene-1,4-diamine, 0.69 g (0.76 mmol) of 2-bromo-9,9'-spirobi [fluorene] and 8.92 g (25.17 mmol) of 10.0 g (25.17 mmol) mixture of Pd 2 (dba) 3, 0.51 g (2.52 mmol) of P (t-bu) 3, 6.05 g NaO (t-bu) , and toluene (150 ml) of (62.93 mmol), and for 5 hours at 110 ℃ Lt; / RTI > After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 10.27 g (yield: 71%) of the target compound was obtained by column chromatography.
GC-Mass (이론치: 574.71 g/mol, 측정치: 574 g/mol)GC-Mass (calculated: 574.71 g / mol, measured: 574 g / mol)
1H-NMR: δ 4.0 (s, 1H), 6.40 (d, 4H), 6.70 (m, 5H), 7.00 (m, 3H), 8.80 (m, 17H), 7.90 (m, 2H), 8.00 (d, 1H)
7.80 (m, 2H), 8.00 (m, 2H), 7.90 (m, 2H) , 1H)
[준비예 36] [Preparation Example 36] N1-(9,9'-spirobi[fluoren]-2-yl)-N1,N4-di-p-tolylbenzene-1,4-diamine의 합성Synthesis of N1- (9,9'-spirobi [fluoren] -2-yl) -N1, N4-di-p-tolylbenzene-1,4-
질소 기류 하에서 10. g(25.17 mmol)의 2-bromo-9,9'-spirobi[fluorene], 7.26 g(25.17 mmol)의 N1,N4-di-p-tolylbenzene-1,4-diamine, 0.69 g(0.76 mmol)의 Pd2(dba)3, 0.51 g(2.52 mmol)의 P(t-bu)3, 6.05 g(62.93 mmol)의 NaO(t-bu) 및 toluene (150 ml)를 혼합하고 110℃에서 5시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 9.86 g (yield: 65 %)을 획득하였다.(25.17 mmol) of 2-bromo-9,9'-spirobi [fluorene], 7.26 g (25.17 mmol) of N1, N4-di- p-tolylbenzene- 1,4-diamine, 0.69 g (0.76 mmol) of Pd 2 (dba) 3, 0.51 g (2.52 mmol) of P (t-bu) 3, 6.05 g (62.93 mmol) of NaO (t-bu) and toluene Lt; 0 > C for 5 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 9.86 g (yield: 65%) of the desired compound was obtained by column chromatography.
GC-Mass (이론치: 602.76 g/mol, 측정치: 602 g/mol)GC-Mass (theory: 602.76 g / mol, measured: 602 g / mol)
1H-NMR: δ 2.30 (s, 6H), 4.0 (s, 1H), 6.40 (d, 4H), 6.70 (m, 5H), 7.00 (m, 3H), 8.80 (m, 17H), 7.90 (m, 2H), 8.00 (d, 1H)
(M, 3H), 8.80 (m, 17H), 7.90 (m, 5H), 6.70 , ≪ / RTI > 2H), 8.00 (d, 1H)
[준비예 37] [Preparation Example 37] N1-(9,9'-spirobi[fluoren]-2-yl)-N1,N4-di(naphthalen-1-yl)benzene-1,4-diamine의 합성Synthesis of N1- (9,9'-spirobi [fluoren] -2-yl) -N1, N4-di (naphthalen-1-yl) benzene-1,4-diamine
질소 기류 하에서 10. g(25.30 mmol)의 2-bromo-9,9'-spirobi[fluorene], 9.12 g(25.30 mmol)의 N1,N4-di(naphthalen-1-yl)benzene-1,4-diamine, 0.69 g(0.76 mmol)의 Pd2(dba)3, 0.51 g(2.52 mmol)의 P(t-bu)3, 6.08 g(63.24 mmol)의 NaO(t-bu) 및 toluene (150 ml)를 혼합하고 110℃에서 5시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 10.41 g (yield: 61 %)을 획득하였다.N, N4-di (naphthalen-1-yl) benzene-1,4-dicarboxylic acid dihydrochloride was obtained under a nitrogen stream with the addition of 10 g (25.30 mmol) of 2-bromo-9,9'-spirobi [fluorene] diamine, 0.69 g Pd 2 (dba ) of (0.76 mmol) 3, 0.51 g P (t-bu) 3, 6.08 g NaO (t-bu) , and toluene (150 ml) of (63.24 mmol) of (2.52 mmol) Were mixed and stirred at 110 ° C for 5 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 10.41 g (yield: 61%) of the desired compound was obtained by column chromatography.
GC-Mass (이론치: 674.83 g/mol, 측정치: 674 g/mol)GC-Mass (calculated: 674.83 g / mol, measured: 674 g / mol)
1H-NMR: δ 4.0 (s, 1H), 6.40 (d, 4H), 6.70 (m, 5H), 7.00 (m, 5H), 8.80 (m, 17H), 7.90 (m, 2H), 8.00 (d, 1H)
(M, 2H), 8.00 (m, 2H), 7.90 (m, 2H), 7.40 , 1H)
[준비예 38] [Preparation Example 38] N4-(9,9'-spirobi[fluoren]-2-yl)-N4,N4'-diphenyl-[1,1'-biphenyl]-4,4'-diamine의 합성Synthesis of N4- (9,9'-spirobi [fluoren] -2-yl) -N4, N4'-diphenyl- [1,1'-biphenyl] -4,4'-diamine
질소 기류 하에서 10. g(25.30 mmol)의 2-bromo-9,9'-spirobi[fluorene], 8.51 g(25.30 mmol)의 N4,N4'-diphenyl-[1,1'-biphenyl]-4,4'-diamine, 0.69 g(0.76 mmol)의 Pd2(dba)3, 0.51 g(2.52 mmol)의 P(t-bu)3, 6.08 g(63.24 mmol)의 NaO(t-bu) 및 toluene (150 ml)를 혼합하고 110℃에서 5시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 12.18 g (yield: 74 %)을 획득하였다.A solution of 10. g (25.30 mmol) of 2-bromo-9,9'-spirobi [fluorene] and 8.51 g (25.30 mmol) of N4, N4'- diphenyl- [1,1'- biphenyl] 4'-diamine, 0.69 g (0.76 mmol) of Pd 2 (dba) 3, 0.51 g (2.52 mmol) of P (t-bu) 3, 6.08 g (63.24 mmol) NaO (t-bu) , and toluene of ( 150 ml) were mixed and stirred at 110 ° C for 5 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 12.18 g (yield: 74%) of the target compound was obtained by column chromatography.
GC-Mass (이론치: 650.81 g/mol, 측정치: 650 g/mol)GC-Mass (calculated: 650.81 g / mol, measured: 650 g / mol)
1H-NMR: δ 4.0 (s, 1H), 6.35 (d, 10H), 6.70 (m, 20H), 7.50 (m, 6H), 7.80 (d, 1H)
(M, 2H), 7.50 (m, 6H), 7.80 (d, 1H)
[준비예 39] [Preparation Example 39] N4-(9,9'-spirobi[fluoren]-2-yl)-N4,N4'-di-p-tolyl-[1,1'-biphenyl]-4,4'-diamine의 합성Synthesis of N4- (9,9'-spirobi [fluoren] -2-yl) -N4, N4'-di-p-tolyl- [1,1'-biphenyl] -4,4'-diamine
질소 기류 하에서 10. g(25.30 mmol)의 2-bromo-9,9'-spirobi[fluorene], 9.22 g(25.30 mmol)의 N4,N4'-di-p-tolyl-[1,1'-biphenyl]-4,4'-diamine, 0.69 g(0.76 mmol)의 Pd2(dba)3, 0.51 g(2.52 mmol)의 P(t-bu)3, 6.08 g(63.24 mmol)의 NaO(t-bu) 및 toluene (150 ml)를 혼합하고 110℃에서 5시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 12.19 g (yield: 71 %)을 획득하였다.A mixture of 10 g (25.30 mmol) of 2-bromo-9,9'-spirobi [fluorene], 9.22 g (25.30 mmol) of N4, di- p-tolyl- [1,1'-biphenyl ] -4,4'-diamine, 0.69 g (0.76 mmol) Pd 2 (dba) 3, 0.51 g (2.52 mmol) P (t-bu) 3, 6.08 g (63.24 mmol) NaO ) And toluene (150 ml) were mixed and stirred at 110 ° C for 5 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 12.19 g (yield: 71%) of the target compound was obtained by column chromatography.
GC-Mass (이론치: 678.86 g/mol, 측정치: 678 g/mol)GC-Mass (theory: 678.86 g / mol, measured: 678 g / mol)
1H-NMR: δ 2.30 (s, 6H), 4.0 (s, 1H), 6.35 (d, 10H), 6.70 (m, 20H), 7.50 (m, 6H), 7.80 (d, 1H)
(M, 2H), 7.50 (m, 6H), 7.80 (d, IH)
[합성예 1] A-1의 합성[Synthesis Example 1] Synthesis of A-1
질소 기류 하에서 준비예 12 에서 합성된 화합물 10.0 g (22.19 mmol), 7.20 g(22.19 mmol)의 4-bromo-N,N-diphenylaniline, 0.61 g(0.67 mmol)의 Pd2(dba)3, 0.45 g(2.22 mmol)의 P(t-bu)3, 5.33 g(55.49 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 11.55 g (yield: 75 %)을 획득하였다. Nd-diphenylaniline, 0.61 g (0.67 mmol) of Pd 2 (dba) 3, 0.45 g (0.13 mmol) of the compound synthesized in Preparation Example 12, 10.0 g (22.19 mmol) (2.22 mmol) of P (t-bu) 3, 5.33 g (55.49 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 11.55 g (yield: 75%) of the target compound was obtained by column chromatography.
GC-Mass (이론치: 693.88 g/mol, 측정치: 693 g/mol)
GC-Mass (calculated: 693.88 g / mol, measured: 693 g / mol)
[합성예 2] A-2의 합성[Synthesis Example 2] Synthesis of A-2
질소 기류 하에서 준비예 12 에서 합성된 화합물 10.0 g (22.19 mmol), 7.82 g(22.19 mmol)의 4-bromo-N,N-di-p-tolylaniline, 0.61 g(0.67 mmol)의 Pd2(dba)3, 0.45 g(2.22 mmol)의 P(t-bu)3, 5.33 g(55.49 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 12.98 g (yield: 81 %)을 획득하였다. Pd 2 (dba) of 4-bromo-N, N-di-p-tolylaniline and 0.61 g (0.67 mmol) of compound 10.0 g (22.19 mmol) synthesized in Preparation Example 12, 7.82 g (22.19 mmol) 3, 0.45 g (2.22 mmol) of P (t-bu) 3, 5.33 g (55.49 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 12.98 g (yield: 81%) of the target compound was obtained by column chromatography.
GC-Mass (이론치: 721.93 g/mol, 측정치: 721 g/mol)
GC-Mass (calculated: 721.93 g / mol, measured: 721 g / mol)
[합성예 3] A-3의 합성[Synthesis Example 3] Synthesis of A-3
질소 기류 하에서 준비예 12 에서 합성된 화합물 10.0 g (22.19 mmol), 10.57 g(22.19 mmol)의 N-([1,1'-biphenyl]-4-yl)-N-(4-bromophenyl)-[1,1'-biphenyl]-4-amine, 0.61 g(0.67 mmol)의 Pd2(dba)3, 0.45 g(2.22 mmol)의 P(t-bu)3, 5.33 g(55.49 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 15.21 g (yield: 75 %)을 획득하였다. 10.0 g (22.19 mmol) of the compound synthesized in Preparation Example 12 and 10.57 g (22.19 mmol) of N - ([1,1'-biphenyl] -4-yl) -N- (4-bromophenyl) - [ NaO of 1,1'-biphenyl] -4-amine, 0.61 g Pd 2 (dba) of (0.67 mmol) 3, 0.45 g (2.22 mmol) P (t-bu) 3, 5.33 g (55.49 mmol) of ( t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 15.21 g (yield: 75%) of the desired compound was obtained by column chromatography.
GC-Mass (이론치: 846.07 g/mol, 측정치: 846 g/mol)
GC-Mass (calculated: 846.07 g / mol, measured: 846 g / mol)
[합성예 4] A-12의 합성[Synthesis Example 4] Synthesis of A-12
질소 기류 하에서 준비예 12 에서 합성된 화합물 10.0 g (22.19 mmol), 9.42 g(22.19 mmol)의 N-(4-bromophenyl)-N-(naphthalen-1-yl)naphthalen-1-amine, 0.61 g(0.67 mmol)의 Pd2(dba)3, 0.45 g(2.22 mmol)의 P(t-bu)3, 5.33 g(55.49 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 13.22 g (yield: 78 %)을 획득하였다. 10.0 g (22.19 mmol) of the compound synthesized in Preparation Example 12 and 9.42 g (22.19 mmol) of N- (4-bromophenyl) -N- (naphthalen-1-yl) naphthalen- Pd 2 (dba) a 0.67 mmol) 3, 0.45 g ( 2.22 mmol) of P (t-bu) 3, were mixed NaO (t-bu), and toluene (200 ml) of 5.33 g (55.49 mmol) 110 ℃ Lt; / RTI > for 3 h. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 13.22 g (yield: 78%) of the desired compound was obtained by column chromatography.
GC-Mass (이론치: 793.99 g/mol, 측정치: 793 g/mol)
GC-Mass (theory: 793.99 g / mol, measured: 793 g / mol)
[합성예 5] A-11의 합성[Synthesis Example 5] Synthesis of A-11
질소 기류 하에서 준비예 12 에서 합성된 화합물 10.0 g (22.19 mmol), 8.31 g(22.19 mmol)의 N-(4-bromophenyl)-N-phenylnaphthalen-1-amine, 0.61 g(0.67 mmol)의 Pd2(dba)3, 0.45 g(2.22 mmol)의 P(t-bu)3, 5.33 g(55.49 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 13.70 g (yield: 83 %)을 획득하였다. (10.0 g, 22.19 mmol) and 8.31 g (22.19 mmol) of N- (4-bromophenyl) -N-phenylnaphthalen-1-amine and 0.61 g (0.67 mmol) of Pd 2 mixing dba) 3, 0.45 g (2.22 mmol) of P (t-bu) 3, 5.33 g (NaO (t-bu) , and toluene (200 ml) of 55.49 mmol) and stirred at 110 ℃ for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 13.70 g (yield: 83%) of the desired compound was obtained by column chromatography.
GC-Mass (이론치: 743.93 g/mol, 측정치: 743 g/mol)
GC-Mass (743.93 g / mol, measured: 743 g / mol)
[합성예 6] A-89의 합성[Synthesis Example 6] Synthesis of A-89
질소 기류 하에서 준비예 12 에서 합성된 화합물 10.0 g (22.19 mmol), 9.42 g(22.19 mmol)의 N-(4-bromophenyl)-N-(naphthalen-2-yl)naphthalen-2-amine, 0.61 g(0.67 mmol)의 Pd2(dba)3, 0.45 g(2.22 mmol)의 P(t-bu)3, 5.33 g(55.49 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 14.10 g (yield: 80 %)을 획득하였다. 10.0 g (22.19 mmol) of the compound synthesized in Preparation Example 12 and 9.42 g (22.19 mmol) of N- (4-bromophenyl) -N- (naphthalen-2-yl) naphthalen- Pd 2 (dba) a 0.67 mmol) 3, 0.45 g ( 2.22 mmol) of P (t-bu) 3, were mixed NaO (t-bu), and toluene (200 ml) of 5.33 g (55.49 mmol) 110 ℃ Lt; / RTI > for 3 h. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 14.10 g (yield: 80%) of the desired compound was obtained by column chromatography.
GC-Mass (이론치: 793.99 g/mol, 측정치: 793 g/mol)
GC-Mass (theory: 793.99 g / mol, measured: 793 g / mol)
[합성예 7] A-4의 합성[Synthesis Example 7] Synthesis of A-4
질소 기류 하에서 준비예 12 에서 합성된 화합물 10.0 g (22.19 mmol), 10.48 g(22.19 mmol)의 N-([1,1'-biphenyl]-4-yl)-N-(4-chlorophenyl)-9,9-dimethyl-9H-fluoren-2-amine, 0.61 g(0.67 mmol)의 Pd2(dba)3, 0.45 g(2.22 mmol)의 P(t-bu)3, 5.33 g(55.49 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 15.73 g (yield: 85 %)을 획득하였다. 10.0 g (22.19 mmol) of the compound synthesized in Preparation Example 12 and 10.48 g (22.19 mmol) of N - ([1,1'-biphenyl] -4-yl) -N- (4-chlorophenyl) -9 , 9-dimethyl-9H-fluoren -2-amine, 0.61 g (0.67 mmol) of Pd 2 (dba) 3, NaO of 0.45 g P (t-bu) 3, 5.33 g (55.49 mmol) of (2.22 mmol) (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 15.73 g (yield: 85%) of the desired compound was obtained by column chromatography.
GC-Mass (이론치: 886.13 g/mol, 측정치: 886 g/mol)
GC-Mass (calculated: 886.13 g / mol, measured: 886 g / mol)
[합성예 8] A-5의 합성[Synthesis Example 8] Synthesis of A-5
질소 기류 하에서 준비예 12 에서 합성된 화합물 10.0 g (22.19 mmol), 10.12 g(22.19 mmol)의 N-([1,1'-biphenyl]-4-yl)-N-(4-chlorophenyl)phenanthren-2-amine, 0.61 g(0.67 mmol)의 Pd2(dba)3, 0.45 g(2.22 mmol)의 P(t-bu)3, 5.33 g(55.49 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 16.41 g (yield: 75 %)을 획득하였다. 10.0 g (22.19 mmol) of the compound synthesized in Preparation Example 12 and 10.12 g (22.19 mmol) of N - ([1,1'-biphenyl] -4-yl) -N- (4-chlorophenyl) phenanthren- (T-bu) and 5.33 g (55.49 mmol) of Pd 2 (dba) 3, 0.45 g (2.22 mmol) ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 16.41 g (yield: 75%) of the target compound was obtained by column chromatography.
GC-Mass (이론치: 870.09 g/mol, 측정치: 870 g/mol)
GC-Mass (calculated: 870.09 g / mol, measured: 870 g / mol)
[합성예 9] A-6의 합성[Synthesis Example 9] Synthesis of A-6
질소 기류 하에서 준비예 12 에서 합성된 화합물 10.0 g (22.19 mmol), 10.12 g(22.19 mmol)의 N-([1,1'-biphenyl]-4-yl)-N-(4-chlorophenyl)phenanthren-9-amine, 0.61 g(0.67 mmol)의 Pd2(dba)3, 0.45 g(2.22 mmol)의 P(t-bu)3, 5.33 g(55.49 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 15.45 g (yield: 80 %)을 획득하였다. 10.0 g (22.19 mmol) of the compound synthesized in Preparation Example 12 and 10.12 g (22.19 mmol) of N - ([1,1'-biphenyl] -4-yl) -N- (4-chlorophenyl) phenanthren- 9-amine, 0.61 g Pd 2 (dba) of (0.67 mmol) 3, 0.45 g (2.22 mmol) of P (t-bu) 3, NaO (t-bu) , and toluene (200 of 5.33 g (55.49 mmol) ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 15.45 g (yield: 80%) of the title compound was obtained by column chromatography.
GC-Mass (이론치: 870.09 g/mol, 측정치: 870 g/mol)
GC-Mass (calculated: 870.09 g / mol, measured: 870 g / mol)
[합성예 10] A-8의 합성[Synthesis Example 10] Synthesis of A-8
질소 기류 하에서 준비예 12 에서 합성된 화합물 10.0 g (22.19 mmol), 11.23 g(22.19 mmol)의 N-([1,1'-biphenyl]-4-yl)-N-(4-chlorophenyl)triphenylen-2-amine, 0.61 g(0.67 mmol)의 Pd2(dba)3, 0.45 g(2.22 mmol)의 P(t-bu)3, 5.33 g(55.49 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 15.93 g (yield: 73 %)을 획득하였다. 10.0 g (22.19 mmol) of the compound synthesized in Preparation Example 12 and 11.23 g (22.19 mmol) of N - ([1,1'-biphenyl] -4-yl) -N- (4- chlorophenyl) triphenylen- (T-bu) and 5.33 g (55.49 mmol) of Pd 2 (dba) 3, 0.45 g (2.22 mmol) ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 15.93 g (yield: 73%) of the title compound was obtained by column chromatography.
GC-Mass (이론치: 920.15 g/mol, 측정치: 920 g/mol)
GC-Mass (calculated: 920.15 g / mol, measured: 920 g / mol)
[합성예 11] A-14의 합성[Synthesis Example 11] Synthesis of A-14
질소 기류 하에서 준비예 12 에서 합성된 화합물 10.0 g (22.19 mmol), 9.09 g(22.19 mmol)의 N-([1,1'-biphenyl]-4-yl)-N-(4-chlorophenyl)naphthalen-1-amine, 0.61 g(0.67 mmol)의 Pd2(dba)3, 0.45 g(2.22 mmol)의 P(t-bu)3, 5.33 g(55.49 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 14.20 g (yield: 87 %)을 획득하였다. 10.0 g (22.19 mmol) of the compound synthesized in Preparation Example 12 and 9.09 g (22.19 mmol) of N - ([1,1'-biphenyl] -4-yl) -N- (4-chlorophenyl) naphthalen- (T-bu) and 5.33 g (55.49 mmol) of Pd 2 (dba) 3, 0.45 g (2.22 mmol) ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 14.20 g (yield: 87%) of the desired compound was obtained by column chromatography.
GC-Mass (이론치: 820.03 g/mol, 측정치: 820 g/mol)
GC-Mass (calculated: 820.03 g / mol, measured: 820 g / mol)
[합성예 12] A-68의 합성[Synthesis Example 12] Synthesis of A-68
질소 기류 하에서 준비예 12 에서 합성된 화합물 10.0 g (22.19 mmol), 9.09 g(22.19 mmol)의 N-([1,1'-biphenyl]-4-yl)-N-(4-chlorophenyl)naphthalen-2-amine, 0.61 g(0.67 mmol)의 Pd2(dba)3, 0.45 g(2.22 mmol)의 P(t-bu)3, 5.33 g(55.49 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 13.65 g (yield: 75 %)을 획득하였다. 10.0 g (22.19 mmol) of the compound synthesized in Preparation Example 12 and 9.09 g (22.19 mmol) of N - ([1,1'-biphenyl] -4-yl) -N- (4-chlorophenyl) naphthalen- (T-bu) and 5.33 g (55.49 mmol) of Pd 2 (dba) 3, 0.45 g (2.22 mmol) ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 13.65 g (yield: 75%) of the desired compound was obtained by column chromatography.
GC-Mass (이론치: 820.03 g/mol, 측정치: 820 g/mol)
GC-Mass (calculated: 820.03 g / mol, measured: 820 g / mol)
[합성예 13] A-18의 합성[Synthesis Example 13] Synthesis of A-18
질소 기류 하에서 준비예 12 에서 합성된 화합물 10.0 g (22.19 mmol), 9.90 g(22.19 mmol)의 N-([1,1'-biphenyl]-4-yl)-N-(4-chlorophenyl)dibenzo[b,d]furan-2-amine, 0.61 g(0.67 mmol)의 Pd2(dba)3, 0.45 g(2.22 mmol)의 P(t-bu)3, 5.33 g(55.49 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 14.32 g (yield: 67 %)을 획득하였다. 10.0 g (22.19 mmol) of the compound synthesized in Preparation Example 12 and 9.90 g (22.19 mmol) of N - ([1,1'-biphenyl] -4-yl) -N- (4-chlorophenyl) dibenzo [ b, d] furan-2-amine, 0.61 g (0.67 mmol) Pd 2 (dba) 3, 0.45 g (2.22 mmol) P (t- bu) 3, 5.33 g (55.49 mmol) Bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 14.32 g (yield: 67%) of the target compound was obtained by column chromatography.
GC-Mass (이론치: 860.50 g/mol, 측정치: 860 g/mol)
GC-Mass (calculated: 860.50 g / mol, measured: 860 g / mol)
[합성예 14] A-19의 합성[Synthesis Example 14] Synthesis of A-19
질소 기류 하에서 준비예 12 에서 합성된 화합물 10.0 g (22.19 mmol), 11.59 g(22.19 mmol)의 N-(4-chlorophenyl)-N-(4-(dibenzo[b,d]furan-4-yl)phenyl)-[1,1'-biphenyl]-4-amine, 0.61 g(0.67 mmol)의 Pd2(dba)3, 0.45 g(2.22 mmol)의 P(t-bu)3, 5.33 g(55.49 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 13.92 g (yield: 73 %)을 획득하였다. Dibenzo [b, d] furan-4-yl) -benzonitrile (10.0 g, 22.19 mmol) synthesized in Preparation Example 12 and 11.59 g (22.19 mmol) P (t-bu) 3, 5.33 g (55.49 mmol) of Pd 2 (dba) 3, 0.45 g (2.22 mmol) of Phenyl- ) NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 13.92 g (yield: 73%) of the desired compound was obtained by column chromatography.
GC-Mass (이론치: 936.15 g/mol, 측정치: 936 g/mol)
GC-Mass (calculated: 936.15 g / mol, measured: 936 g / mol)
[합성예 15] A-20의 합성[Synthesis Example 15] Synthesis of A-20
질소 기류 하에서 준비예 12 에서 합성된 화합물 10.0 g (22.19 mmol), 10.25 g(22.19 mmol)의 N-([1,1'-biphenyl]-4-yl)-N-(4-chlorophenyl)dibenzo[b,d]thiophen-2-amine, 0.61 g(0.67 mmol)의 Pd2(dba)3, 0.45 g(2.22 mmol)의 P(t-bu)3, 5.33 g(55.49 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 14.19 g (yield: 75 %)을 획득하였다. 10.0 g (22.19 mmol) of the compound synthesized in Preparation Example 12 and 10.25 g (22.19 mmol) of N - ([1,1'-biphenyl] -4-yl) -N- (4-chlorophenyl) dibenzo [ b, d] thiophen-2-amine, 0.61 g (0.67 mmol) Pd 2 (dba) 3, 0.45 g (2.22 mmol) P (t- bu) 3, 5.33 g (55.49 mmol) Bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 14.19 g (yield: 75%) of the desired compound was obtained by column chromatography.
GC-Mass (이론치: 876.12 g/mol, 측정치: 876 g/mol)
GC-Mass (calculated: 876.12 g / mol, measured: 876 g / mol)
[합성예 16] A-25의 합성[Synthesis Example 16] Synthesis of A-25
질소 기류 하에서 준비예 12 에서 합성된 화합물 10.0 g (22.19 mmol), 8.88 g(22.19 mmol)의 4'-bromo-N,N-diphenyl-[1,1'-biphenyl]-4-amine, 0.61 g(0.67 mmol)의 Pd2(dba)3, 0.45 g(2.22 mmol)의 P(t-bu)3, 5.33 g(55.49 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 12.82 g (yield: 81 %)을 획득하였다. 10.0 g (22.19 mmol) of the compound synthesized in Preparation Example 12 and 8.88 g (22.19 mmol) of 4'-bromo-N, N-diphenyl- [1,1'- biphenyl] -4- Pd 2 of (0.67 mmol) (dba) 3 , 0.45 g (2.22 mmol) of P (t-bu) 3, were mixed NaO (t-bu), and toluene (200 ml) of 5.33 g (55.49 mmol) 110 Lt; 0 > C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 12.82 g (yield: 81%) of the target compound was obtained by column chromatography.
GC-Mass (이론치: 769.97 g/mol, 측정치: 769 g/mol)
GC-Mass (calculated: 769.97 g / mol, measured: 769 g / mol)
[합성예 17] A-43의 합성[Synthesis Example 17] Synthesis of A-43
질소 기류 하에서 준비예 12 에서 합성된 화합물 10.0 g (22.19 mmol), 10.00 g(22.19 mmol)의 N-(4'-bromo-[1,1'-biphenyl]-4-yl)-N-phenylnaphthalen-1-amine, 0.61 g(0.67 mmol)의 Pd2(dba)3, 0.45 g(2.22 mmol)의 P(t-bu)3, 5.33 g(55.49 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 14.74 g (yield: 76 %)을 획득하였다. 10.0 g (22.19 mmol) of the compound synthesized in Preparation Example 12 and 10.00 g (22.19 mmol) of N- (4'-bromo- [1,1'-biphenyl] -4-yl) -N-phenylnaphthalen- (T-bu) and 5.33 g (55.49 mmol) of Pd 2 (dba) 3, 0.45 g (2.22 mmol) ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 14.74 g (yield: 76%) of the target compound was obtained by column chromatography.
GC-Mass (이론치: 820.03 g/mol, 측정치: 820 g/mol)
GC-Mass (calculated: 820.03 g / mol, measured: 820 g / mol)
[합성예 18] A-44의 합성[Synthesis Example 18] Synthesis of A-44
질소 기류 하에서 준비예 12 에서 합성된 화합물 10.0 g (22.19 mmol), 11.11 g(22.19 mmol)의 N-(4'-bromo-[1,1'-biphenyl]-4-yl)-N-(naphthalen-1-yl)naphthalen-1-amine, 0.61 g(0.67 mmol)의 Pd2(dba)3, 0.45 g(2.22 mmol)의 P(t-bu)3, 5.33 g(55.49 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 15.45 g (yield: 80 %)을 획득하였다. 10.0 g (22.19 mmol) of the compound synthesized in Preparation Example 12 and 11.11 g (22.19 mmol) of N- (4'-bromo- [1,1'-biphenyl] -4-yl) -N- -1-yl) naphthalen-1- amine, 0.61 g (0.67 mmol Pd 2 (dba) a) 3, 0.45 g (2.22 mmol ) of P (t-bu) 3, NaO (t of 5.33 g (55.49 mmol) -bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 15.45 g (yield: 80%) of the title compound was obtained by column chromatography.
GC-Mass (이론치: 870.09 g/mol, 측정치: 870 g/mol)
GC-Mass (calculated: 870.09 g / mol, measured: 870 g / mol)
[합성예 19] A-26의 합성[Synthesis Example 19] Synthesis of A-26
질소 기류 하에서 준비예 12 에서 합성된 화합물 10.0 g (22.19 mmol), 9.51 g(22.19 mmol)의 4'-bromo-N,N-di-p-tolyl-[1,1'-biphenyl]-4-amine, 0.61 g(0.67 mmol)의 Pd2(dba)3, 0.45 g(2.22 mmol)의 P(t-bu)3, 5.33 g(55.49 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 14.17 g (yield: 68 %)을 획득하였다. 10.0 g (22.19 mmol) of the compound synthesized in Preparation Example 12 and 9.51 g (22.19 mmol) of 4'-bromo-N, N-di-p-tolyl- [1,1'- amine, 0.61 g Pd 2 (dba ) of (0.67 mmol) 3, 0.45 g (2.22 mmol) P (t-bu) 3, NaO (t-bu) , and toluene (200 ml) of 5.33 g (55.49 mmol) of Were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 14.17 g (yield: 68%) of the desired compound was obtained by column chromatography.
GC-Mass (이론치: 798.02 g/mol, 측정치: 798 g/mol)
GC-Mass (theory: 798.02 g / mol, measured: 798 g / mol)
[합성예 20] A-27의 합성[Synthesis Example 20] Synthesis of A-27
질소 기류 하에서 준비예 12 에서 합성된 화합물 10.0 g (22.19 mmol), 12.26 g(22.19 mmol)의 N,N-di([1,1'-biphenyl]-4-yl)-4'-bromo-[1,1'-biphenyl]-4-amine, 0.61 g(0.67 mmol)의 Pd2(dba)3, 0.45 g(2.22 mmol)의 P(t-bu)3, 5.33 g(55.49 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 13.92 g (yield: 65 %)을 획득하였다. 10.0 g (22.19 mmol) of the compound synthesized in Preparation Example 12 and 12.26 g (22.19 mmol) of N, N-di ([1,1'- biphenyl] -4-yl) -4'- NaO of 1,1'-biphenyl] -4-amine, 0.61 g Pd 2 (dba) of (0.67 mmol) 3, 0.45 g (2.22 mmol) P (t-bu) 3, 5.33 g (55.49 mmol) of ( t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 13.92 g (yield: 65%) of the desired compound was obtained by column chromatography.
GC-Mass (이론치: 922.16 g/mol, 측정치: 922 g/mol)
GC-Mass (calculated: 922.16 g / mol, measured: 922 g / mol)
[합성예 21] A-28의 합성[Synthesis Example 21] Synthesis of A-28
질소 기류 하에서 준비예 12 에서 합성된 화합물 10.0 g (22.19 mmol), 13.15 g(22.19 mmol)의 N-([1,1'-biphenyl]-4-yl)-N-(4'-bromo-[1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine, 0.61 g(0.67 mmol)의 Pd2(dba)3, 0.45 g(2.22 mmol)의 P(t-bu)3, 5.33 g(55.49 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 14.95 g (yield: 70 %)을 획득하였다. 10.0 g (22.19 mmol) of the compound synthesized in Preparation Example 12 and 13.15 g (22.19 mmol) of N - ([1,1'-biphenyl] -4-yl) -N- Pd 2 (dba) 3, 0.45 g (2.22 mmol) of P ( 1, 1'-biphenyl] -4,9-dimethyl-9H-fluoren- t-bu) 3, 5.33 g (55.49 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 14.95 g (yield: 70%) of the target compound was obtained by column chromatography.
GC-Mass (이론치: 962.23 g/mol, 측정치: 962 g/mol)
GC-Mass (calculated: 962.23 g / mol, measured: 962 g / mol)
[합성예 22] A-37의 합성[Synthesis Example 22] Synthesis of A-37
질소 기류 하에서 준비예 12 에서 합성된 화합물 10.0 g (22.19 mmol), 11.81 g(22.19 mmol)의 N-([1,1'-biphenyl]-4-yl)-N-(4'-chloro-[1,1'-biphenyl]-4-yl)phenanthren-2-amine, 0.61 g(0.67 mmol)의 Pd2(dba)3, 0.45 g(2.22 mmol)의 P(t-bu)3, 5.33 g(55.49 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 14.70 g (yield: 72 %)을 획득하였다. 10.0 g (22.19 mmol) of the compound synthesized in Preparation Example 12 and 11.81 g (22.19 mmol) of N - ([1,1'-biphenyl] -4-yl) -N- 1,1'-biphenyl] -4-yl) phenanthren-2-amine, 0.61 g (Pd 2 (dba of 0.67 mmol)) 3, 0.45 g 3, 5.33 g P (t-bu) of (2.22 mmol) ( 55.49 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 14.70 g (yield: 72%) of the desired compound was obtained by column chromatography.
GC-Mass (이론치: 946.18 g/mol, 측정치: 946 g/mol)
GC-Mass (946.18 g / mol, measured: 946 g / mol)
[합성예 23] A-39의 합성[Synthesis Example 23] Synthesis of A-39
질소 기류 하에서 준비예 12 에서 합성된 화합물 10.0 g (22.19 mmol), 11.81 g(22.19 mmol)의 N-([1,1'-biphenyl]-4-yl)-N-(4'-chloro-[1,1'-biphenyl]-4-yl)phenanthren-9-amine, 0.61 g(0.67 mmol)의 Pd2(dba)3, 0.45 g(2.22 mmol)의 P(t-bu)3, 5.33 g(55.49 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 15.75 g (yield: 75 %)을 획득하였다. 10.0 g (22.19 mmol) of the compound synthesized in Preparation Example 12 and 11.81 g (22.19 mmol) of N - ([1,1'-biphenyl] -4-yl) -N- 1,1'-biphenyl] -4-yl) phenanthren-9-amine, 0.61 g (Pd 2 (dba of 0.67 mmol)) 3, 0.45 g 3, 5.33 g P (t-bu) of (2.22 mmol) ( 55.49 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 15.75 g (yield: 75%) of the desired compound was obtained by column chromatography.
GC-Mass (이론치: 946.18 g/mol, 측정치: 946 g/mol)
GC-Mass (946.18 g / mol, measured: 946 g / mol)
[합성예 24] A-40의 합성[Synthesis Example 24] Synthesis of A-40
질소 기류 하에서 준비예 12 에서 합성된 화합물 10.0 g (22.19 mmol), 12.92 g(22.19 mmol)의 N-([1,1'-biphenyl]-4-yl)-N-(4'-chloro-[1,1'-biphenyl]-4-yl)triphenylen-2-amine, 0.61 g(0.67 mmol)의 Pd2(dba)3, 0.45 g(2.22 mmol)의 P(t-bu)3, 5.33 g(55.49 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 16.58 g (yield: 80 %)을 획득하였다. 10.0 g (22.19 mmol) of the compound synthesized in Preparation Example 12 and 12.92 g (22.19 mmol) of N - ([1,1'-biphenyl] -4-yl) -N- 1,1'-biphenyl] -4-yl) triphenylen-2-amine, 0.61 g (Pd 2 (dba of 0.67 mmol)) 3, 0.45 g 3, 5.33 g P (t-bu) of (2.22 mmol) ( 55.49 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 16.58 g (yield: 80%) of the target compound was obtained by column chromatography.
GC-Mass (이론치: 996.13 g/mol, 측정치: 996 g/mol)
GC-Mass (996.13 g / mol, measured: 996 g / mol)
[합성예 25] A-46의 합성[Synthesis Example 25] Synthesis of A-46
질소 기류 하에서 준비예 12 에서 합성된 화합물 10.0 g (22.19 mmol), 10.70 g(22.19 mmol)의 N-([1,1'-biphenyl]-4-yl)-N-(4'-chloro-[1,1'-biphenyl]-4-yl)naphthalen-1-amine, 0.61 g(0.67 mmol)의 Pd2(dba)3, 0.45 g(2.22 mmol)의 P(t-bu)3, 5.33 g(55.49 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 14.92 g (yield: 84 %)을 획득하였다. 10.0 g (22.19 mmol) of the compound synthesized in Preparation Example 12 and 10.70 g (22.19 mmol) of N - ([1,1'-biphenyl] -4-yl) -N- 1,1'-biphenyl] -4-yl) naphthalen-1-amine, 0.61 g (Pd 2 (dba of 0.67 mmol)) 3, 0.45 g 3, 5.33 g P (t-bu) of (2.22 mmol) ( 55.49 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 14.92 g (yield: 84%) of the title compound was obtained by column chromatography.
GC-Mass (이론치: 896.13 g/mol, 측정치: 896 g/mol)
GC-Mass (896.13 g / mol, measured: 896 g / mol)
[합성예 26] A-50의 합성[Synthesis Example 26] Synthesis of A-50
질소 기류 하에서 준비예 12 에서 합성된 화합물 10.0 g (22.19 mmol), 11.59 g(22.19 mmol)의 N-([1,1'-biphenyl]-4-yl)-N-(4'-chloro-[1,1'-biphenyl]-4-yl)dibenzo[b,d]furan-2-amine, 0.61 g(0.67 mmol)의 Pd2(dba)3, 0.45 g(2.22 mmol)의 P(t-bu)3, 5.33 g(55.49 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 17.45 g (yield: 80 %)을 획득하였다. 10.0 g (22.19 mmol) of the compound synthesized in Preparation Example 12 and 11.59 g (22.19 mmol) of N - ([1,1'-biphenyl] -4-yl) -N- (T-bu) of Pd 2 (dba) 3, 0.45 g (2.22 mmol) of Pd 2 (dibenzo [b, d] furan- ) 3, 5.33 g (55.49 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 17.45 g (yield: 80%) of the desired compound was obtained by column chromatography.
GC-Mass (이론치: 936.15 g/mol, 측정치: 936 g/mol)
GC-Mass (calculated: 936.15 g / mol, measured: 936 g / mol)
[합성예 27] A-52의 합성[Synthesis Example 27] Synthesis of A-52
질소 기류 하에서 준비예 12 에서 합성된 화합물 10.0 g (22.19 mmol), 11.94 g(22.19 mmol)의 N-([1,1'-biphenyl]-4-yl)-N-(4'-chloro-[1,1'-biphenyl]-4-yl)dibenzo[b,d]thiophen-2-amine, 0.61 g(0.67 mmol)의 Pd2(dba)3, 0.45 g(2.22 mmol)의 P(t-bu)3, 5.33 g(55.49 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 16.91 g (yield: 80 %)을 획득하였다. 10.0 g (22.19 mmol) of the compound synthesized in Preparation Example 12 and 11.94 g (22.19 mmol) of N - ([1,1'-biphenyl] -4-yl) -N- 1,1'-biphenyl] -4-yl) dibenzo [b, d] thiophen-2-amine, 0.61 g (0.67 mmol) of Pd 2 (dba) 3, 0.45 g (2.22 mmol) of P (t-bu ) 3, 5.33 g (55.49 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 16.91 g (yield: 80%) of the target compound was obtained by column chromatography.
GC-Mass (이론치: 952.21 g/mol, 측정치: 952 g/mol)
GC-Mass (calculated: 952.21 g / mol, measured: 952 g / mol)
[합성예 28] A-70의 합성[Synthesis Example 28] Synthesis of A-70
질소 기류 하에서 준비예 19 에서 합성된 화합물 10.0 g (18.99 mmol), 6.16 g(18.99 mmol)의 4-bromo-N,N-diphenylaniline, 0.52 g(0.57 mmol)의 Pd2(dba)3, 0.38 g(1.90 mmol)의 P(t-bu)3, 4.56 g(47.47 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 10.96 g (yield: 75 %)을 획득하였다. The synthesized compound from Preparation Example 19 was conducted in a nitrogen atmosphere 10.0 g (18.99 mmol), 6.16 g (18.99 mmol) 4-bromo-N, N-diphenylaniline, 0.52 g Pd 2 (dba) of (0.57 mmol) 3, 0.38 g of (1.90 mmol) of P (t-bu) 3, 4.56 g (47.47 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 10.96 g (yield: 75%) of the desired compound was obtained by column chromatography.
GC-Mass (이론치: 769.97 g/mol, 측정치: 769 g/mol)
GC-Mass (calculated: 769.97 g / mol, measured: 769 g / mol)
[합성예 29] A-71의 합성[Synthesis Example 29] Synthesis of A-71
질소 기류 하에서 준비예 19 에서 합성된 화합물 10.0 g (18.99 mmol), 7.11 g(18.99 mmol)의 4-bromo-N,N-diphenylaniline, 0.52 g(0.57 mmol)의 Pd2(dba)3, 0.38 g(1.90 mmol)의 P(t-bu)3, 4.56 g(47.47 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 11.68 g (yield: 70 %)을 획득하였다. Pd 2 (dba) 3 of 4-bromo-N, N-diphenylaniline, 0.52 g (0.57 mmol) of 7.11 g (18.99 mmol) of the compound synthesized in Preparation Example 19 , 0.38 g (1.90 mmol) of P (t-bu) 3, 4.56 g (47.47 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 11.68 g (yield: 70%) of the desired compound was obtained by column chromatography.
GC-Mass (이론치: 820.03 g/mol, 측정치: 820 g/mol)
GC-Mass (calculated: 820.03 g / mol, measured: 820 g / mol)
[합성예 30] A-29의 합성[Synthesis Example 30] Synthesis of A-29
질소 기류 하에서 준비예 19 에서 합성된 화합물 10.0 g (18.99 mmol), 7.60 g(18.99 mmol)의 4'-bromo-N,N-diphenyl-[1,1'-biphenyl]-4-amine, 0.52 g(0.57 mmol)의 Pd2(dba)3, 0.38 g(1.90 mmol)의 P(t-bu)3, 4.56 g(47.47 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 11.25 g (yield: 65 %)을 획득하였다. 10.0 g (18.99 mmol) of the compound synthesized in Preparation Example 19 and 7.60 g (18.99 mmol) of 4'-bromo-N, N-diphenyl- [1,1'- biphenyl] -4- (0.57 mmol) of Pd 2 (dba) 3, 0.38 g (1.90 mmol) of P (t-bu) 3, 4.56 g (47.47 mmol) of NaO (t-bu) and toluene Lt; 0 > C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 11.25 g (yield: 65%) of the desired compound was obtained by column chromatography.
GC-Mass (이론치: 846.07 g/mol, 측정치: 846 g/mol)
GC-Mass (calculated: 846.07 g / mol, measured: 846 g / mol)
[합성예 31] A-33의 합성[Synthesis Example 31] Synthesis of A-33
질소 기류 하에서 준비예 19 에서 합성된 화합물 10.0 g (18.99 mmol), 8.55 g(18.99 mmol)의 N-(4'-bromo-[1,1'-biphenyl]-4-yl)-N-phenylnaphthalen-1-amine, 0.52 g(0.57 mmol)의 Pd2(dba)3, 0.38 g(1.90 mmol)의 P(t-bu)3, 4.56 g(47.47 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 11.06 g (yield: 62 %)을 획득하였다. 10.0 g (18.99 mmol) of the compound synthesized in Preparation Example 19 and 8.55 g (18.99 mmol) of N- (4'-bromo- [1,1'-biphenyl] -4-yl) -N-phenylnaphthalen- 1-amine, 0.52 g Pd 2 (dba) of (0.57 mmol) 3, 0.38 g (1.90 mmol) of P (t-bu) 3, NaO (t-bu) , and toluene (200 of 4.56 g (47.47 mmol) ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 11.06 g (yield: 62%) of the target compound was obtained by column chromatography.
GC-Mass (이론치: 896.13 g/mol, 측정치: 896 g/mol)
GC-Mass (896.13 g / mol, measured: 896 g / mol)
[합성예 32] A-32의 합성[Synthesis Example 32] Synthesis of A-32
질소 기류 하에서 준비예 12 에서 합성된 화합물 10.0 g (22.19 mmol), 9.59 g(22.19 mmol)의 4''-chloro-N,N-diphenyl-[1,1':4',1''-terphenyl]-4-amine, 0.61 g(0.67 mmol)의 Pd2(dba)3, 0.45 g(2.22 mmol)의 P(t-bu)3, 5.33 g(55.49 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 14.08 g (yield: 75 %)을 획득하였다. 10.0 g (22.19 mmol) of the compound synthesized in Preparation Example 12 and 9.59 g (22.19 mmol) of 4'-chloro-N, N-diphenyl- [1,1 ': 4', 1 " ] -4-amine, 0.61 g (0.67 mmol) Pd 2 (dba) 3, 0.45 g (2.22 mmol) P (t-bu) 3, 5.33 g (55.49 mmol) NaO (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 14.08 g (yield: 75%) of the target compound was obtained by column chromatography.
GC-Mass (이론치: 846.07 g/mol, 측정치: 846 g/mol)
GC-Mass (calculated: 846.07 g / mol, measured: 846 g / mol)
[합성예 33] A-81의 합성[Synthesis Example 33] Synthesis of A-81
질소 기류 하에서 준비예 28 에서 합성된 화합물 10.0 g (17.40 mmol), 5.64 g(17.40 mmol)의 4-bromo-N,N-diphenylaniline, 0.48 g(0.52 mmol)의 Pd2(dba)3, 0.35 g(1.74 mmol)의 P(t-bu)3, 4.18 g(43.50 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 10.11 g (yield: 71 %)을 획득하였다. N, diphenylaniline, 0.48 g (0.52 mmol) of Pd 2 (dba) 3, 0.35 g (4.40 mmol) of the compound synthesized in Preparation Example 28, 5.64 g (1.74 mmol) of P (t-bu) 3, 4.18 g (43.50 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 10.11 g (yield: 71%) of the target compound was obtained by column chromatography.
GC-Mass (이론치: 818.01 g/mol, 측정치: 818 g/mol)
GC-Mass (theory: 818.01 g / mol, measurement: 818 g / mol)
[합성예 34] A-82의 합성[Synthesis Example 34] Synthesis of A-82
질소 기류 하에서 준비예 28 에서 합성된 화합물 10.0 g (17.40 mmol), 6.13 g(17.40 mmol)의 4-bromo-N,N-di-p-tolylaniline, 0.48 g(0.52 mmol)의 Pd2(dba)3, 0.35 g(1.74 mmol)의 P(t-bu)3, 4.18 g(43.50 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 11.04 g (yield: 75 %)을 획득하였다. Pd 2 (dba) of 4-bromo-N, N-di-p-tolylaniline and 0.48 g (0.52 mmol) of the compound synthesized in Preparation Example 28 (10.0 g, 17.40 mmol), 6.13 g 3, 0.35 g (1.74 mmol) of P (t-bu) 3, 4.18 g (43.50 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 11.04 g (yield: 75%) of the title compound was obtained by column chromatography.
GC-Mass (이론치: 846.07 g/mol, 측정치: 846 g/mol)
GC-Mass (calculated: 846.07 g / mol, measured: 846 g / mol)
[합성예 35] A-85의 합성[Synthesis Example 35] Synthesis of A-85
질소 기류 하에서 준비예 28 에서 합성된 화합물 10.0 g (17.40 mmol), 8.32 g(17.40 mmol)의 N-([1,1'-biphenyl]-4-yl)-N-(4-bromophenyl)-[1,1'-biphenyl]-4-amine, 0.48 g(0.52 mmol)의 Pd2(dba)3, 0.35 g(1.74 mmol)의 P(t-bu)3, 4.18 g(43.50 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 11.82 g (yield: 70 %)을 획득하였다. 10.0 g (17.40 mmol) of the compound synthesized in Preparation Example 28 and 8.32 g (17.40 mmol) of N - ([1,1'-biphenyl] -4-yl) -N- (4-bromophenyl) - [ NaO of 1,1'-biphenyl] -4-amine, 0.48 g Pd 2 (dba) of (0.52 mmol) 3, 0.35 g P (t-bu) 3, 4.18 g (43.50 mmol) of (1.74 mmol) ( t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 11.82 g (yield: 70%) of the target compound was obtained by column chromatography.
GC-Mass (이론치: 970.21 g/mol, 측정치: 970 g/mol)
GC-Mass (calculated: 970.21 g / mol, measured: 970 g / mol)
[합성예 36] A-84의 합성[Synthesis Example 36] Synthesis of A-84
질소 기류 하에서 준비예 28 에서 합성된 화합물 10.0 g (17.40 mmol), 7.38 g(17.40 mmol)의 N-(4-bromophenyl)-N-(naphthalen-1-yl)naphthalen-1-amine, 0.48 g(0.52 mmol)의 Pd2(dba)3, 0.35 g(1.74 mmol)의 P(t-bu)3, 4.18 g(43.50 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 12.78 g (yield: 80 %)을 획득하였다. (10.0 g, 17.40 mmol), 7.38 g (17.40 mmol) of N- (4-bromophenyl) -N- (naphthalen-1-yl) naphthalen- Pd 2 (dba) a 0.52 mmol) 3, 0.35 g ( 1.74 mmol) of P (t-bu) 3, 4.18 g (43.50 mixture of NaO (t-bu), and toluene (200 ml) of mmol) and 110 ℃ Lt; / RTI > for 3 h. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 12.78 g (yield: 80%) of the target compound was obtained by column chromatography.
GC-Mass (이론치: 918.13 g/mol, 측정치: 918 g/mol)
GC-Mass (calculated: 918.13 g / mol, measured: 918 g / mol)
[합성예 37] A-83의 합성[Synthesis Example 37] Synthesis of A-83
질소 기류 하에서 준비예 28 에서 합성된 화합물 10.0 g (17.40 mmol), 6.51 g(17.40 mmol)의 N-(4-bromophenyl)-N-phenylnaphthalen-1-amine, 0.48 g(0.52 mmol)의 Pd2(dba)3, 0.35 g(1.74 mmol)의 P(t-bu)3, 4.18 g(43.50 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 11.33 g (yield: 75 %)을 획득하였다. (4-bromophenyl) -N-phenylnaphthalen-1-amine and 0.48 g (0.52 mmol) of Pd 2 (0.45 mmol) were added to a solution of 10.0 g (17.40 mmol) mixing dba) 3, 0.35 g (NaO (t-bu) , and toluene (200 ml) of P (t-bu) 3, 4.18 g (43.50 mmol) of a 1.74 mmol) and stirred at 110 ℃ for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 11.33 g (yield: 75%) of the desired compound was obtained by column chromatography.
GC-Mass (이론치: 868.07 g/mol, 측정치: 868 g/mol)
GC-Mass (calculated: 868.07 g / mol, measured: 868 g / mol)
[합성예 38] A-86의 합성[Synthesis Example 38] Synthesis of A-86
질소 기류 하에서 준비예 28 에서 합성된 화합물 10.0 g (17.40 mmol), 6.97 g(17.40 mmol)의 4'-bromo-N,N-diphenyl-[1,1'-biphenyl]-4-amine, 0.48 g(0.52 mmol)의 Pd2(dba)3, 0.35 g(1.74 mmol)의 P(t-bu)3, 4.18 g(43.50 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 10.11 g (yield: 65 %)을 획득하였다. 10.0 g (17.40 mmol) of the compound synthesized in Preparation Example 28 and 6.97 g (17.40 mmol) of 4'-bromo-N, N-diphenyl- [1,1'- biphenyl] -4-amine and 0.48 g (0.52 mmol) of Pd 2 (dba) 3, 0.35 g (1.74 mmol) of P (t-bu) 3, 4.18 g (43.50 mmol) of NaO (t-bu) and toluene Lt; 0 > C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 10.11 g (yield: 65%) of the target compound was obtained by column chromatography.
GC-Mass (이론치: 818.01 g/mol, 측정치: 818 g/mol)
GC-Mass (theory: 818.01 g / mol, measurement: 818 g / mol)
[합성예 39] A-87의 합성[Synthesis Example 39] Synthesis of A-87
질소 기류 하에서 준비예 28 에서 합성된 화합물 10.0 g (17.40 mmol), 7.45 g(17.40 mmol)의 4'-bromo-N,N-di-p-tolyl-[1,1'-biphenyl]-4-amine, 0.48 g(0.52 mmol)의 Pd2(dba)3, 0.35 g(1.74 mmol)의 P(t-bu)3, 4.18 g(43.50 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 10.75 g (yield: 67 %)을 획득하였다. 10.0 g (17.40 mmol) of the compound synthesized in Preparation Example 28 and 7.45 g (17.40 mmol) of 4'-bromo-N, N-di-p-tolyl- [1,1'- amine, 0.48 g Pd 2 (dba ) of (0.52 mmol) 3, 0.35 g P (t-bu) 3, 4.18 g NaO (t-bu) , and toluene (200 ml) of (43.50 mmol) of (1.74 mmol) Were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 10.75 g (yield: 67%) of the desired compound was obtained by column chromatography.
GC-Mass (이론치: 922.16 g/mol, 측정치: 922 g/mol)
GC-Mass (calculated: 922.16 g / mol, measured: 922 g / mol)
[합성예 40] A-88의 합성[Synthesis Example 40] Synthesis of A-88
질소 기류 하에서 준비예 28 에서 합성된 화합물 10.0 g (17.40 mmol), 7.84 g(17.40 mmol)의 N-(4'-bromo-[1,1'-biphenyl]-4-yl)-N-phenylnaphthalen-1-amine, 0.48 g(0.52 mmol)의 Pd2(dba)3, 0.35 g(1.74 mmol)의 P(t-bu)3, 4.18 g(43.50 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 11.50 g (yield: 70 %)을 획득하였다. 10.0 g (17.40 mmol) of the compound synthesized in Preparation Example 28 and 7.84 g (17.40 mmol) of N- (4'-bromo- [1,1'-biphenyl] -4-yl) -N-phenylnaphthalen- 1-amine, 0.48 g Pd 2 (dba) of (0.52 mmol) 3, 0.35 g (1.74 mmol) of P (t-bu) 3, 4.18 g NaO (t-bu) , and toluene (200 of (43.50 mmol) ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 11.50 g (yield: 70%) of the desired compound was obtained by column chromatography.
GC-Mass (이론치: 944.17 g/mol, 측정치: 944 g/mol)
GC-Mass (944.17 g / mol, measured: 944 g / mol)
[합성예 41] A-89의 합성[Synthesis Example 41] Synthesis of A-89
질소 기류 하에서 준비예 29 에서 합성된 화합물 10.0 g (17.46 mmol), 5.66 g(17.46 mmol)의 4-bromo-N,N-diphenylaniline, 0.48 g(0.52 mmol)의 Pd2(dba)3, 0.35 g(1.75 mmol)의 P(t-bu)3, 4.20 g(43.65 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 9.12 g (yield: 64 %)을 획득하였다. N, diphenylaniline, 0.48 g (0.52 mmol) of Pd 2 (dba) 3, 0.35 g (17.46 mmol) of the compound synthesized in Preparation Example 29, 5.66 g (1.75 mmol) of P (t-bu) 3, 4.20 g (43.65 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 9.12 g (yield: 64%) of the desired compound was obtained by column chromatography.
GC-Mass (이론치: 816.00 g/mol, 측정치: 816 g/mol)
GC-Mass (calculated: 816.00 g / mol, measured: 816 g / mol)
[합성예 42] A-90의 합성[Synthesis Example 42] Synthesis of A-90
질소 기류 하에서 준비예 29 에서 합성된 화합물 10.0 g (17.46 mmol), 6.15 g(17.46 mmol)의 4-bromo-N,N-di-p-tolylaniline, 0.48 g(0.52 mmol)의 Pd2(dba)3, 0.35 g(1.75 mmol)의 P(t-bu)3, 4.20 g(43.65 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 10.91 g (yield: 74 %)을 획득하였다. Pd 2 (dba) of 4-bromo-N, N-di-p-tolylaniline and 0.48 g (0.52 mmol) of compound 10.0 g (17.46 mmol) prepared in Preparation Example 29, 6.15 g (17.46 mmol) 3, 0.35 g (1.75 mmol) of P (t-bu) 3, 4.20 g (43.65 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 10.91 g (yield: 74%) of the desired compound was obtained by column chromatography.
GC-Mass (이론치: 844.05 g/mol, 측정치: 844 g/mol)
GC-Mass (calculated: 844.05 g / mol, measured: 844 g / mol)
[합성예 43] A-93의 합성[Synthesis Example 43] Synthesis of A-93
질소 기류 하에서 준비예 29 에서 합성된 화합물 10.0 g (17.46 mmol), 8.32 g(17.46 mmol)의 N-([1,1'-biphenyl]-4-yl)-N-(4-bromophenyl)-[1,1'-biphenyl]-4-amine, 0.48 g(0.52 mmol)의 Pd2(dba)3, 0.35 g(1.75 mmol)의 P(t-bu)3, 4.20 g(43.65 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 12.55 g (yield: 75 %)을 획득하였다. 10.0 g (17.46 mmol) of the compound synthesized in Preparation Example 29 and 8.32 g (17.46 mmol) of N - ([1,1'-biphenyl] -4-yl) -N- (4-bromophenyl) - [ NaO of 1,1'-biphenyl] -4-amine, 0.48 g Pd 2 (dba) of (0.52 mmol) 3, 0.35 g P (t-bu) of (1.75 mmol) 3, 4.20 g (43.65 mmol) ( t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 12.55 g (yield: 75%) of the target compound was obtained by column chromatography.
GC-Mass (이론치: 958.19 g/mol, 측정치: 958 g/mol)
GC-Mass (958.19 g / mol, measured: 958 g / mol)
[합성예 44] A-92의 합성[Synthesis Example 44] Synthesis of A-92
질소 기류 하에서 준비예 29 에서 합성된 화합물 10.0 g (17.46 mmol), 7.41 g(17.46 mmol)의 N-(4-bromophenyl)-N-(naphthalen-1-yl)naphthalen-1-amine, 0.48 g(0.52 mmol)의 Pd2(dba)3, 0.35 g(1.75 mmol)의 P(t-bu)3, 4.20 g(43.65 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 11.20 g (yield: 70 %)을 획득하였다. (10.0 g, 17.46 mmol) and 7.41 g (17.46 mmol) of N- (4-bromophenyl) -N- (naphthalen-1-yl) naphthalen- Pd 2 (dba) a 0.52 mmol) 3, 0.35 g ( 1.75 mmol) of P (t-bu) 3, were mixed 4.20 g (NaO (t-bu ) , and toluene (200 ml) of 43.65 mmol) 110 ℃ Lt; / RTI > for 3 h. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 11.20 g (yield: 70%) of the target compound was obtained by column chromatography.
GC-Mass (이론치: 916.12 g/mol, 측정치: 916 g/mol)
GC-Mass (calculated: 916.12 g / mol, measured: 916 g / mol)
[합성예 45] A-91의 합성[Synthesis Example 45] Synthesis of A-91
질소 기류 하에서 준비예 29 에서 합성된 화합물 10.0 g (17.46 mmol), 6.54 g(17.46 mmol)의 N-(4-bromophenyl)-N-phenylnaphthalen-1-amine, 0.48 g(0.52 mmol)의 Pd2(dba)3, 0.35 g(1.75 mmol)의 P(t-bu)3, 4.20 g(43.65 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 11.34 g (yield: 75 %)을 획득하였다. (4-bromophenyl) -N-phenylnaphthalen-1-amine and 0.48 g (0.52 mmol) of Pd 2 (0.45 mmol) were added to a solution of 10.0 g (17.46 mmol) of the compound prepared in Preparation Example 29, 6.54 g mixing dba) 3, 0.35 g (1.75 mmol) of P (t-bu) 3, 4.20 g (NaO (t-bu) , and toluene (200 ml) of 43.65 mmol) and stirred at 110 ℃ for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 11.34 g (yield: 75%) of the desired compound was obtained by column chromatography.
GC-Mass (이론치: 866.06 g/mol, 측정치: 866 g/mol)
GC-Mass (calculated: 866.06 g / mol, measured: 866 g / mol)
[합성예 46] A-94의 합성[Synthesis Example 46] Synthesis of A-94
질소 기류 하에서 준비예 29 에서 합성된 화합물 10.0 g (17.46 mmol), 6.99 g(17.46 mmol)의 4'-bromo-N,N-diphenyl-[1,1'-biphenyl]-4-amine, 0.48 g(0.52 mmol)의 Pd2(dba)3, 0.35 g(1.75 mmol)의 P(t-bu)3, 4.20 g(43.65 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 12.93 g (yield: 83 %)을 획득하였다. 10.0 g (17.46 mmol) of the compound synthesized in Preparation Example 29 and 6.99 g (17.46 mmol) of 4'-bromo-N, N-diphenyl- [1,1'- biphenyl] -4-amine and 0.48 g (0.52 mmol) of Pd 2 (dba) 3, 0.35 g (1.75 mmol) of P (t-bu) 3, 4.20 g (43.65 mmol) of NaO (t-bu) and toluene Lt; 0 > C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 12.93 g (yield: 83%) of the desired compound was obtained by column chromatography.
GC-Mass (이론치: 892.09 g/mol, 측정치: 892 g/mol)
GC-Mass (892.09 g / mol, measured: 892 g / mol)
[합성예 47] A-95의 합성[Synthesis Example 47] Synthesis of A-95
질소 기류 하에서 준비예 29 에서 합성된 화합물 10.0 g (17.46 mmol), 7.48 g(17.46 mmol)의 4'-bromo-N,N-di-p-tolyl-[1,1'-biphenyl]-4-amine, 0.48 g(0.52 mmol)의 Pd2(dba)3, 0.35 g(1.75 mmol)의 P(t-bu)3, 4.20 g(43.65 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 12.21 g (yield: 76 %)을 획득하였다. To a solution of 10.0 g (17.46 mmol) of the compound prepared in Preparation 29 and 7.48 g (17.46 mmol) of 4'-bromo-N, N-di-p-tolyl- [1,1'- amine, 0.48 g Pd 2 (dba ) of (0.52 mmol) 3, 0.35 g (1.75 mmol) P (t-bu) 3, 4.20 g NaO (t-bu) , and toluene (200 ml) of (43.65 mmol) of Were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 12.21 g (yield: 76%) of the target compound was obtained by column chromatography.
GC-Mass (이론치: 920.15 g/mol, 측정치: 920 g/mol)
GC-Mass (calculated: 920.15 g / mol, measured: 920 g / mol)
[합성예 48] A-96의 합성[Synthesis Example 48] Synthesis of A-96
질소 기류 하에서 준비예 29 에서 합성된 화합물 10.0 g (17.46 mmol), 7.86 g(17.46 mmol)의 N-(4'-bromo-[1,1'-biphenyl]-4-yl)-N-phenylnaphthalen-1-amine, 0.48 g(0.52 mmol)의 Pd2(dba)3, 0.35 g(1.75 mmol)의 P(t-bu)3, 4.20 g(43.65 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 13.33 g (yield: 81 %)을 획득하였다. 10.0 g (17.46 mmol) of the compound synthesized in Preparation Example 29 and 7.86 g (17.46 mmol) of N- (4'-bromo- [1,1'-biphenyl] -4-yl) -N-phenylnaphthalen- (T-bu) 3 and 4.20 g (43.65 mmol) of Pd 2 (dba) 3, 0.35 g (1.75 mmol) ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 13.33 g (yield: 81%) of the target compound was obtained by column chromatography.
GC-Mass (이론치: 942.15 g/mol, 측정치: 942 g/mol)
GC-Mass (calculated: 942.15 g / mol, measured: 942 g / mol)
[합성예 49] B-1의 합성[Synthesis Example 49] Synthesis of B-1
질소 기류 하에서 준비예 20 에서 합성된 화합물 14.05 g (31.04 mmol), 10.0 g(31.04 mmol)의 9-(4-bromophenyl)-9H-carbazole, 0.85 g(0.93 mmol)의 Pd2(dba)3, 0.63 g(3.10 mmol)의 P(t-bu)3, 7.46 g(77.59 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 18.74 g (yield: 87 %)을 획득하였다. (4-bromophenyl) -9H-carbazole, 0.85 g (0.93 mmol) of Pd 2 (dba) 3, 10.0 g (31.04 mmol) of the compound synthesized in Preparation Example 20 , 0.63 g (3.10 mmol) of P (t-bu) 3, 7.46 g (77.59 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 18.74 g (yield: 87%) of the target compound was obtained by column chromatography.
GC-Mass (이론치: 693.88 g/mol, 측정치: 693 g/mol)
GC-Mass (calculated: 693.88 g / mol, measured: 693 g / mol)
[합성예 50] B-2의 합성[Synthesis Example 50] Synthesis of B-2
질소 기류 하에서 준비예 21 에서 합성된 화합물 14.92 g (31.04 mmol), 10.0 g(31.04 mmol)의 9-(4-bromophenyl)-9H-carbazole, 0.85 g(0.93 mmol)의 Pd2(dba)3, 0.63 g(3.10 mmol)의 P(t-bu)3, 7.46 g(77.59 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 19.05 g (yield: 85 %)을 획득하였다. 9- (4-bromophenyl) -9H-carbazole, 0.85 g (0.93 mmol) of Pd 2 (dba) 3, 10.0 g (31.04 mmol) of the compound synthesized in Preparation Example 21 , 0.63 g (3.10 mmol) of P (t-bu) 3, 7.46 g (77.59 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 19.05 g (yield: 85%) of the target compound was obtained by column chromatography.
GC-Mass (이론치: 721.93 g/mol, 측정치: 721 g/mol)
GC-Mass (calculated: 721.93 g / mol, measured: 721 g / mol)
[합성예 51] B-4의 합성[Synthesis Example 51] Synthesis of B-4
질소 기류 하에서 준비예 22 에서 합성된 화합물 17.15 g (31.04 mmol), 10.0 g(31.04 mmol)의 9-(4-bromophenyl)-9H-carbazole, 0.85 g(0.93 mmol)의 Pd2(dba)3, 0.63 g(3.10 mmol)의 P(t-bu)3, 7.46 g(77.59 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 18.91 g (yield: 72 %)을 획득하였다. The synthesized compound from Preparation Example 22 was conducted in a nitrogen atmosphere 17.15 g (31.04 mmol), 10.0 g 9- (4-bromophenyl) -9H-carbazole, 0.85 g (0.93 mmol) Pd 2 (dba) of (31.04 mmol) 3, 0.63 g (3.10 mmol) of P (t-bu) 3, 7.46 g (77.59 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 18.91 g (yield: 72%) of the desired compound was obtained by column chromatography.
GC-Mass (이론치: 793.99 g/mol, 측정치: 793.99 g/mol)
GC-Mass (calculated: 793.99 g / mol, measured: 793.99 g / mol)
[합성예 52] B-3의 합성[Synthesis Example 52] Synthesis of B-3
질소 기류 하에서 준비예 23 에서 합성된 화합물 18.77 g (31.04 mmol), 10.0 g(31.04 mmol)의 9-(4-bromophenyl)-9H-carbazole, 0.85 g(0.93 mmol)의 Pd2(dba)3, 0.63 g(3.10 mmol)의 P(t-bu)3, 7.46 g(77.59 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 18.91 g (yield: 72 %)을 획득하였다. The synthesized compound from Preparation Example 23 was conducted in a nitrogen atmosphere 18.77 g (31.04 mmol), 10.0 g 9- (4-bromophenyl) -9H-carbazole, 0.85 g (0.93 mmol) Pd 2 (dba) of (31.04 mmol) 3, 0.63 g (3.10 mmol) of P (t-bu) 3, 7.46 g (77.59 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 18.91 g (yield: 72%) of the desired compound was obtained by column chromatography.
GC-Mass (이론치: 847.07 g/mol, 측정치: 847 g/mol)
GC-Mass (calculated: 847.07 g / mol, measured: 847 g / mol)
[합성예 53] B-11의 합성[Synthesis Example 53] Synthesis of B-11
질소 기류 하에서 준비예 20 에서 합성된 화합물 14.05 g (31.04 mmol), 10.0 g(31.04 mmol)의 9-(3-bromophenyl)-9H-carbazole, 0.85 g(0.93 mmol)의 Pd2(dba)3, 0.63 g(3.10 mmol)의 P(t-bu)3, 7.46 g(77.59 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 18.74 g (yield: 87 %)을 획득하였다. The synthesized compound from Preparation Example 20 was conducted in a nitrogen atmosphere 14.05 g (31.04 mmol), 10.0 g 9- (3-bromophenyl) -9H-carbazole, 0.85 g (0.93 mmol) Pd 2 (dba) of (31.04 mmol) 3, 0.63 g (3.10 mmol) of P (t-bu) 3, 7.46 g (77.59 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 18.74 g (yield: 87%) of the target compound was obtained by column chromatography.
GC-Mass (이론치: 693.88 g/mol, 측정치: 693 g/mol)
GC-Mass (calculated: 693.88 g / mol, measured: 693 g / mol)
[합성예 54] B-12의 합성[Synthesis Example 54] Synthesis of B-12
질소 기류 하에서 준비예 21 에서 합성된 화합물 14.92 g (31.04 mmol), 10.0 g(31.04 mmol)의 9-(3-bromophenyl)-9H-carbazole, 0.85 g(0.93 mmol)의 Pd2(dba)3, 0.63 g(3.10 mmol)의 P(t-bu)3, 7.46 g(77.59 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 19.05 g (yield: 85 %)을 획득하였다. 9- (3-bromophenyl) -9H-carbazole, 0.85 g (0.93 mmol) of Pd 2 (dba) 3, 10.0 g (31.04 mmol) of the compound synthesized in Preparation Example 21 , 0.63 g (3.10 mmol) of P (t-bu) 3, 7.46 g (77.59 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 19.05 g (yield: 85%) of the target compound was obtained by column chromatography.
GC-Mass (이론치: 721.93 g/mol, 측정치: 721 g/mol)
GC-Mass (calculated: 721.93 g / mol, measured: 721 g / mol)
[합성예 55] B-14의 합성[Synthesis Example 55] Synthesis of B-14
질소 기류 하에서 준비예 22 에서 합성된 화합물 17.15 g (31.04 mmol), 10.0 g(31.04 mmol)의 9-(3-bromophenyl)-9H-carbazole, 0.85 g(0.93 mmol)의 Pd2(dba)3, 0.63 g(3.10 mmol)의 P(t-bu)3, 7.46 g(77.59 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 18.91 g (yield: 72 %)을 획득하였다. The synthesized compound from Preparation Example 22 was conducted in a nitrogen atmosphere 17.15 g (31.04 mmol), 10.0 g 9- (3-bromophenyl) -9H-carbazole, 0.85 g (0.93 mmol) Pd 2 (dba) of (31.04 mmol) 3, 0.63 g (3.10 mmol) of P (t-bu) 3, 7.46 g (77.59 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 18.91 g (yield: 72%) of the desired compound was obtained by column chromatography.
GC-Mass (이론치: 793.99 g/mol, 측정치: 793.99 g/mol)
GC-Mass (calculated: 793.99 g / mol, measured: 793.99 g / mol)
[합성예 56] B-13의 합성[Synthesis Example 56] Synthesis of B-13
질소 기류 하에서 준비예 23 에서 합성된 화합물 10.0 g (31.04 mmol), 9.42 g(31.04 mmol)의 N-(4-bromophenyl)-N-(naphthalen-2-yl)naphthalen-2-amine, 0.85 g(0.93 mmol)의 Pd2(dba)3, 0.63 g(3.10 mmol)의 P(t-bu)3, 7.46 g(77.59 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 14.10 g (yield: 80 %)을 획득하였다. (10.0 g, 31.04 mmol) and 9.42 g (31.04 mmol) of N- (4-bromophenyl) -N- (naphthalen-2-yl) naphthalen- Pd 2 (dba) a 0.93 mmol) 3, 0.63 g ( 3.10 mmol) of P (t-bu) 3, 7.46 g (77.59 mmol) of the mixture of NaO (t-bu), and toluene (200 ml) 110 ℃ Lt; / RTI > for 3 h. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 14.10 g (yield: 80%) of the desired compound was obtained by column chromatography.
GC-Mass (이론치: 793.99 g/mol, 측정치: 793 g/mol)
GC-Mass (theory: 793.99 g / mol, measured: 793 g / mol)
[합성예 57] B-29의 합성[Synthesis Example 57] Synthesis of B-29
질소 기류 하에서 준비예 24 에서 합성된 화합물 16.41 g (31.04 mmol), 10.0 g(31.04 mmol)의 9-(4-bromophenyl)-9H-carbazole, 0.85 g(0.93 mmol)의 Pd2(dba)3, 0.63 g(3.10 mmol)의 P(t-bu)3, 7.46 g(77.59 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 17.21 g (yield: 72 %)을 획득하였다. The synthesized compound from Preparation Example 24 was conducted in a nitrogen atmosphere 16.41 g (31.04 mmol), 10.0 g 9- (4-bromophenyl) -9H-carbazole, 0.85 g (0.93 mmol) Pd 2 (dba) of (31.04 mmol) 3, 0.63 g (3.10 mmol) of P (t-bu) 3, 7.46 g (77.59 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 17.21 g (yield: 72%) of the target compound was obtained by column chromatography.
GC-Mass (이론치: 769.97 g/mol, 측정치: 769 g/mol)
GC-Mass (calculated: 769.97 g / mol, measured: 769 g / mol)
[합성예 58] B-30의 합성[Synthesis Example 58] Synthesis of B-30
질소 기류 하에서 준비예 25 에서 합성된 화합물 17.27 g (31.04 mmol), 10.0 g(31.04 mmol)의 9-(4-bromophenyl)-9H-carbazole, 0.85 g(0.93 mmol)의 Pd2(dba)3, 0.63 g(3.10 mmol)의 P(t-bu)3, 7.46 g(77.59 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 19.81 g (yield: 80 %)을 획득하였다. The synthesized compound from Preparation Example 25 was conducted in a nitrogen atmosphere 17.27 g (31.04 mmol), 10.0 g 9- (4-bromophenyl) -9H-carbazole, 0.85 g (0.93 mmol) Pd 2 (dba) of (31.04 mmol) 3, 0.63 g (3.10 mmol) of P (t-bu) 3, 7.46 g (77.59 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 19.81 g (yield: 80%) of the target compound was obtained by column chromatography.
GC-Mass (이론치: 798.02 g/mol, 측정치: 798 g/mol)
GC-Mass (theory: 798.02 g / mol, measured: 798 g / mol)
[합성예 59] B-32의 합성[Synthesis Example 59] Synthesis of B-32
질소 기류 하에서 준비예 26 에서 합성된 화합물 19.52 g (31.04 mmol), 10.0 g(31.04 mmol)의 9-(4-bromophenyl)-9H-carbazole, 0.85 g(0.93 mmol)의 Pd2(dba)3, 0.63 g(3.10 mmol)의 P(t-bu)3, 7.46 g(77.59 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 20.25 g (yield: 75 %)을 획득하였다. The synthesized compound from Preparation Example 26 was conducted in a nitrogen atmosphere 19.52 g (31.04 mmol), 10.0 g 9- (4-bromophenyl) -9H-carbazole, 0.85 g (0.93 mmol) Pd 2 (dba) of (31.04 mmol) 3, 0.63 g (3.10 mmol) of P (t-bu) 3, 7.46 g (77.59 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 20.25 g (yield: 75%) of the desired compound was obtained by column chromatography.
GC-Mass (이론치: 870.09 g/mol, 측정치: 870 g/mol)
GC-Mass (calculated: 870.09 g / mol, measured: 870 g / mol)
[합성예 60] B-31의 합성[Synthesis Example 60] Synthesis of B-31
질소 기류 하에서 준비예 27 에서 합성된 화합물 21.13 g (31.04 mmol), 10.0 g(31.04 mmol)의 9-(4-bromophenyl)-9H-carbazole, 0.85 g(0.93 mmol)의 Pd2(dba)3, 0.63 g(3.10 mmol)의 P(t-bu)3, 7.46 g(77.59 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 19.18 g (yield: 67 %)을 획득하였다. The synthesized compound from Preparation Example 27 was conducted in a nitrogen atmosphere 21.13 g (31.04 mmol), 10.0 g 9- (4-bromophenyl) -9H-carbazole, 0.85 g (0.93 mmol) Pd 2 (dba) of (31.04 mmol) 3, 0.63 g (3.10 mmol) of P (t-bu) 3, 7.46 g (77.59 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 19.18 g (yield: 67%) of the target compound was obtained by column chromatography.
GC-Mass (이론치: 922.16 g/mol, 측정치: 922 g/mol)
GC-Mass (calculated: 922.16 g / mol, measured: 922 g / mol)
[합성예 61] B-41의 합성[Synthesis Example 61] Synthesis of B-41
질소 기류 하에서 준비예 24 에서 합성된 화합물 16.41 g (31.04 mmol), 10.0 g(31.04 mmol)의 9-(3-bromophenyl)-9H-carbazole, 0.85 g(0.93 mmol)의 Pd2(dba)3, 0.63 g(3.10 mmol)의 P(t-bu)3, 7.46 g(77.59 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 17.21 g (yield: 72 %)을 획득하였다. The synthesized compound from Preparation Example 24 was conducted in a nitrogen atmosphere 16.41 g (31.04 mmol), 10.0 g 9- (3-bromophenyl) -9H-carbazole, 0.85 g (0.93 mmol) Pd 2 (dba) of (31.04 mmol) 3, 0.63 g (3.10 mmol) of P (t-bu) 3, 7.46 g (77.59 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 17.21 g (yield: 72%) of the target compound was obtained by column chromatography.
GC-Mass (이론치: 769.97 g/mol, 측정치: 769 g/mol)
GC-Mass (calculated: 769.97 g / mol, measured: 769 g / mol)
[합성예 62] B-42의 합성[Synthesis Example 62] Synthesis of B-42
질소 기류 하에서 준비예 25 에서 합성된 화합물 17.27 g (31.04 mmol), 10.0 g(31.04 mmol)의 9-(3-bromophenyl)-9H-carbazole, 0.85 g(0.93 mmol)의 Pd2(dba)3, 0.63 g(3.10 mmol)의 P(t-bu)3, 7.46 g(77.59 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 19.81 g (yield: 80 %)을 획득하였다. The synthesized compound from Preparation Example 25 was conducted in a nitrogen atmosphere 17.27 g (31.04 mmol), 10.0 g 9- (3-bromophenyl) -9H-carbazole, 0.85 g (0.93 mmol) Pd 2 (dba) of (31.04 mmol) 3, 0.63 g (3.10 mmol) of P (t-bu) 3, 7.46 g (77.59 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 19.81 g (yield: 80%) of the target compound was obtained by column chromatography.
GC-Mass (이론치: 798.02 g/mol, 측정치: 798 g/mol)
GC-Mass (theory: 798.02 g / mol, measured: 798 g / mol)
[합성예 63] B-44의 합성[Synthesis Example 63] Synthesis of B-44
질소 기류 하에서 준비예 26 에서 합성된 화합물 19.52 g (31.04 mmol), 10.0 g(31.04 mmol)의 9-(3-bromophenyl)-9H-carbazole, 0.85 g(0.93 mmol)의 Pd2(dba)3, 0.63 g(3.10 mmol)의 P(t-bu)3, 7.46 g(77.59 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 20.25 g (yield: 75 %)을 획득하였다. The synthesized compound from Preparation Example 26 was conducted in a nitrogen atmosphere 19.52 g (31.04 mmol), 10.0 g 9- (3-bromophenyl) -9H-carbazole, 0.85 g (0.93 mmol) Pd 2 (dba) of (31.04 mmol) 3, 0.63 g (3.10 mmol) of P (t-bu) 3, 7.46 g (77.59 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 20.25 g (yield: 75%) of the desired compound was obtained by column chromatography.
GC-Mass (이론치: 870.09 g/mol, 측정치: 870 g/mol)
GC-Mass (calculated: 870.09 g / mol, measured: 870 g / mol)
[합성예 64] B-43의 합성[Synthesis Example 64] Synthesis of B-43
질소 기류 하에서 준비예 27 에서 합성된 화합물 21.13 g (31.04 mmol), 10.0 g(31.04 mmol)의 9-(3-bromophenyl)-9H-carbazole, 0.85 g(0.93 mmol)의 Pd2(dba)3, 0.63 g(3.10 mmol)의 P(t-bu)3, 7.46 g(77.59 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 19.18 g (yield: 67 %)을 획득하였다. (3-bromophenyl) -9H-carbazole, 0.85 g (0.93 mmol) of Pd 2 (dba) 3, 10.0 g (31.04 mmol) of the compound synthesized in Preparation Example 27 , 0.63 g (3.10 mmol) of P (t-bu) 3, 7.46 g (77.59 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 19.18 g (yield: 67%) of the target compound was obtained by column chromatography.
GC-Mass (이론치: 922.16 g/mol, 측정치: 922 g/mol)
GC-Mass (calculated: 922.16 g / mol, measured: 922 g / mol)
[합성예 65] B-55의 합성[Synthesis Example 65] Synthesis of B-55
질소 기류 하에서 준비예 20 에서 합성된 화합물 11.36 g (25.11 mmol), 10.0 g(25.11 mmol)의 9-(4'-bromo-[1,1'-biphenyl]-4-yl)-9H-carbazole, 0.69 g(0.75 mmol)의 Pd2(dba)3, 0.51 g(2.51 mmol)의 P(t-bu)3, 6.03 g(62.77 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 15.08 g (yield: 78 %)을 획득하였다. 11.36 g (25.11 mmol) of the compound synthesized in Preparation Example 20 and 10.0 g (25.11 mmol) of 9- (4'-bromo- [1,1'- biphenyl] -4-yl) -9H- To a mixture of 0.69 g (0.75 mmol) Pd 2 (dba) 3, 0.51 g (2.51 mmol) P (t-bu) 3, 6.03 g (62.77 mmol) NaO (t- And stirred at 110 < 0 > C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 15.08 g (yield: 78%) of the target compound was obtained by column chromatography.
GC-Mass (이론치: 793.99 g/mol, 측정치: 793 g/mol)
GC-Mass (theory: 793.99 g / mol, measured: 793 g / mol)
[합성예 66] B-56의 합성[Synthesis Example 66] Synthesis of B-56
질소 기류 하에서 준비예 24 에서 합성된 화합물 13.27 g (25.11 mmol), 10.0 g(25.11 mmol)의 9-(4'-bromo-[1,1'-biphenyl]-4-yl)-9H-carbazole, 0.69 g(0.75 mmol)의 Pd2(dba)3, 0.51 g(2.51 mmol)의 P(t-bu)3, 6.03 g(62.77 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 17.21 g (yield: 81 %)을 획득하였다. 13.27 g (25.11 mmol) of the compound synthesized in Preparation Example 24 and 10.0 g (25.11 mmol) of 9- (4'-bromo- [1,1'-biphenyl] -4-yl) -9H- To a mixture of 0.69 g (0.75 mmol) Pd 2 (dba) 3, 0.51 g (2.51 mmol) P (t-bu) 3, 6.03 g (62.77 mmol) NaO (t- And stirred at 110 < 0 > C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 17.21 g (yield: 81%) of the target compound was obtained by column chromatography.
GC-Mass (이론치: 846.07 g/mol, 측정치: 846 g/mol)
GC-Mass (calculated: 846.07 g / mol, measured: 846 g / mol)
[합성예 67] B-71의 합성[Synthesis Example 67] Synthesis of B-71
질소 기류 하에서 준비예 30 에서 합성된 화합물 17.90 g (31.04 mmol), 10.0 g(31.04 mmol)의 9-(4-bromophenyl)-9H-carbazole, 0.85 g(0.93 mmol)의 Pd2(dba)3, 0.63 g(3.10 mmol)의 P(t-bu)3, 7.46 g(77.59 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 16.50 g (yield: 65 %)을 획득하였다. 9- (4-bromophenyl) -9H-carbazole, 0.85 g (0.93 mmol) of Pd 2 (dba) 3, 10.0 g (31.04 mmol) of the compound synthesized in Preparation Example 30 , 0.63 g (3.10 mmol) of P (t-bu) 3, 7.46 g (77.59 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 16.50 g (yield: 65%) of the desired compound was obtained by column chromatography.
GC-Mass (이론치: 818.01 g/mol, 측정치: 818 g/mol)
GC-Mass (theory: 818.01 g / mol, measurement: 818 g / mol)
[합성예 68] B-72의 합성[Synthesis Example 68] Synthesis of B-72
질소 기류 하에서 준비예 31 에서 합성된 화합물 18.77 g (31.04 mmol), 10.0 g(31.04 mmol)의 9-(4-bromophenyl)-9H-carbazole, 0.85 g(0.93 mmol)의 Pd2(dba)3, 0.63 g(3.10 mmol)의 P(t-bu)3, 7.46 g(77.59 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 16.02 g (yield: 61 %)을 획득하였다. The synthesized compound from Preparation Example 31 was conducted in a nitrogen atmosphere 18.77 g (31.04 mmol), 10.0 g 9- (4-bromophenyl) -9H-carbazole, 0.85 g (0.93 mmol) Pd 2 (dba) of (31.04 mmol) 3, 0.63 g (3.10 mmol) of P (t-bu) 3, 7.46 g (77.59 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 16.02 g (yield: 61%) of the target compound was obtained by column chromatography.
GC-Mass (이론치: 846.07 g/mol, 측정치: 846 g/mol)
GC-Mass (calculated: 846.07 g / mol, measured: 846 g / mol)
[합성예 69] B-74의 합성[Synthesis Example 69] Synthesis of B-74
질소 기류 하에서 준비예 32 에서 합성된 화합물 15.96 g (31.04 mmol), 10.0 g(31.04 mmol)의 9-(4-bromophenyl)-9H-carbazole, 0.85 g(0.93 mmol)의 Pd2(dba)3, 0.63 g(3.10 mmol)의 P(t-bu)3, 7.46 g(77.59 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 15.96 g (yield: 56 %)을 획득하였다. 9- (4-bromophenyl) -9H-carbazole, 0.85 g (0.93 mmol) of Pd 2 (dba) 3, 10.0 g (31.04 mmol) of the compound synthesized in Preparation Example 32 , 0.63 g (3.10 mmol) of P (t-bu) 3, 7.46 g (77.59 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 15.96 g (yield: 56%) of the title compound was obtained by column chromatography.
GC-Mass (이론치: 918.13 g/mol, 측정치: 918 g/mol)
GC-Mass (calculated: 918.13 g / mol, measured: 918 g / mol)
[합성예 70] B-76의 합성[Synthesis Example 70] Synthesis of B-76
질소 기류 하에서 준비예 33 에서 합성된 화합물 20.26 g (31.04 mmol), 10.0 g(31.04 mmol)의 9-(4-bromophenyl)-9H-carbazole, 0.85 g(0.93 mmol)의 Pd2(dba)3, 0.63 g(3.10 mmol)의 P(t-bu)3, 7.46 g(77.59 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 18.59 g (yield: 67 %)을 획득하였다. The synthesized compound from Preparation Example 33 was conducted in a nitrogen atmosphere 20.26 g (31.04 mmol), 10.0 g 9- (4-bromophenyl) -9H-carbazole, 0.85 g (0.93 mmol) Pd 2 (dba) of (31.04 mmol) 3, 0.63 g (3.10 mmol) of P (t-bu) 3, 7.46 g (77.59 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 18.59 g (yield: 67%) of the desired compound was obtained by column chromatography.
GC-Mass (이론치: 894.11 g/mol, 측정치: 894 g/mol)
GC-Mass (894.11 g / mol, measured: 894 g / mol)
[합성예 71] B-77의 합성[Synthesis Example 71] Synthesis of B-77
질소 기류 하에서 준비예 34 에서 합성된 화합물 21.13 g (31.04 mmol), 10.0 g(31.04 mmol)의 9-(4-bromophenyl)-9H-carbazole, 0.85 g(0.93 mmol)의 Pd2(dba)3, 0.63 g(3.10 mmol)의 P(t-bu)3, 7.46 g(77.59 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 20.03 g (yield: 70 %)을 획득하였다. The synthesized compound from Preparation Example 34 was conducted in a nitrogen atmosphere 21.13 g (31.04 mmol), 10.0 g 9- (4-bromophenyl) -9H-carbazole, 0.85 g (0.93 mmol) Pd 2 (dba) of (31.04 mmol) 3, 0.63 g (3.10 mmol) of P (t-bu) 3, 7.46 g (77.59 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 20.03 g (yield: 70%) of the target compound was obtained by column chromatography.
GC-Mass (이론치: 922.16 g/mol, 측정치: 922 g/mol)
GC-Mass (calculated: 922.16 g / mol, measured: 922 g / mol)
[합성예 72] B-81의 합성[Synthesis Example 72] Synthesis of B-81
질소 기류 하에서 준비예 35 에서 합성된 화합물 17.84 g (31.04 mmol), 10.0 g(31.04 mmol)의 9-(4-bromophenyl)-9H-carbazole, 0.85 g(0.93 mmol)의 Pd2(dba)3, 0.63 g(3.10 mmol)의 P(t-bu)3, 7.46 g(77.59 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 18.99 g (yield: 75 %)을 획득하였다. 9- (4-bromophenyl) -9H-carbazole, 0.85 g (0.93 mmol) of Pd 2 (dba) 3, 10.0 g (31.04 mmol) of the compound synthesized in Preparation Example 35 , 0.63 g (3.10 mmol) of P (t-bu) 3, 7.46 g (77.59 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 18.99 g (yield: 75%) of the desired compound was obtained by column chromatography.
GC-Mass (이론치: 816.00 g/mol, 측정치: 816 g/mol)
GC-Mass (calculated: 816.00 g / mol, measured: 816 g / mol)
[합성예 73] B-82의 합성[Synthesis Example 73] Synthesis of B-82
질소 기류 하에서 준비예 36 에서 합성된 화합물 18.71 g (31.04 mmol), 10.0 g(31.04 mmol)의 9-(4-bromophenyl)-9H-carbazole, 0.85 g(0.93 mmol)의 Pd2(dba)3, 0.63 g(3.10 mmol)의 P(t-bu)3, 7.46 g(77.59 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 20.17 g (yield: 77 %)을 획득하였다. The synthesized compound from Preparation Example 36 was conducted in a nitrogen atmosphere 18.71 g (31.04 mmol), 10.0 g 9- (4-bromophenyl) -9H-carbazole, 0.85 g (0.93 mmol) Pd 2 (dba) of (31.04 mmol) 3, 0.63 g (3.10 mmol) of P (t-bu) 3, 7.46 g (77.59 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 20.17 g (yield: 77%) of the target compound was obtained by column chromatography.
GC-Mass (이론치: 844.05 g/mol, 측정치: 844 g/mol)
GC-Mass (calculated: 844.05 g / mol, measured: 844 g / mol)
[합성예 74] B-84의 합성[Synthesis Example 74] Synthesis of B-84
질소 기류 하에서 준비예 37 에서 합성된 화합물 20.94 g (31.04 mmol), 10.0 g(31.04 mmol)의 9-(4-bromophenyl)-9H-carbazole, 0.85 g(0.93 mmol)의 Pd2(dba)3, 0.63 g(3.10 mmol)의 P(t-bu)3, 7.46 g(77.59 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 18.20 g (yield: 64 %)을 획득하였다. The synthesized compound from Preparation Example 37 was conducted in a nitrogen atmosphere 20.94 g (31.04 mmol), 10.0 g 9- (4-bromophenyl) -9H-carbazole, 0.85 g (0.93 mmol) Pd 2 (dba) of (31.04 mmol) 3, 0.63 g (3.10 mmol) of P (t-bu) 3, 7.46 g (77.59 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 18.20 g (yield: 64%) of the desired compound was obtained by column chromatography.
GC-Mass (이론치: 916.12 g/mol, 측정치: 916 g/mol)
GC-Mass (calculated: 916.12 g / mol, measured: 916 g / mol)
[합성예 75] B-85의 합성[Synthesis Example 75] Synthesis of B-85
질소 기류 하에서 준비예 38 에서 합성된 화합물 20.20 g (31.04 mmol), 10.0 g(31.04 mmol)의 9-(4-bromophenyl)-9H-carbazole, 0.85 g(0.93 mmol)의 Pd2(dba)3, 0.63 g(3.10 mmol)의 P(t-bu)3, 7.46 g(77.59 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 16.89 g (yield: 61 %)을 획득하였다. (20.0 g, 31.04 mmol), 10.0 g (31.04 mmol) of 9- (4-bromophenyl) -9H-carbazole and 0.85 g (0.93 mmol) of Pd 2 (dba) 3 in a nitrogen stream , 0.63 g (3.10 mmol) of P (t-bu) 3, 7.46 g (77.59 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 16.89 g (yield: 61%) of the target compound was obtained by column chromatography.
GC-Mass (이론치: 892.09 g/mol, 측정치: 892 g/mol)
GC-Mass (892.09 g / mol, measured: 892 g / mol)
[합성예 76] B-86의 합성[Synthesis Example 76] Synthesis of B-86
질소 기류 하에서 준비예 39 에서 합성된 화합물 21.07 g (31.04 mmol), 10.0 g(31.04 mmol)의 9-(4-bromophenyl)-9H-carbazole, 0.85 g(0.93 mmol)의 Pd2(dba)3, 0.63 g(3.10 mmol)의 P(t-bu)3, 7.46 g(77.59 mmol)의 NaO(t-bu) 및 toluene (200 ml)를 혼합하고 110℃에서 3시간 동안 교반하였다. 반응 종결 후 다이클로로메탄으로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 17.14 g (yield: 60 %)을 획득하였다. The synthesized compound from Preparation Example 39 was conducted in a nitrogen atmosphere 21.07 g (31.04 mmol), 10.0 g 9- (4-bromophenyl) -9H-carbazole, 0.85 g (0.93 mmol) Pd 2 (dba) of (31.04 mmol) 3, 0.63 g (3.10 mmol) of P (t-bu) 3, 7.46 g (77.59 mmol) of NaO (t-bu) and toluene (200 ml) were mixed and stirred at 110 ° C for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was filtered through MgSO 4 . After removing the solvent of the filtered organic layer, 17.14 g (yield: 60%) of the desired compound was obtained by column chromatography.
GC-Mass (이론치: 920.15 g/mol, 측정치: 920 g/mol)
GC-Mass (calculated: 920.15 g / mol, measured: 920 g / mol)
[실시예 1] 유기 EL 소자의 제조[Example 1] Production of organic EL device
ITO (Indium tin oxide)가 1500 Å 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 5 분간 세정한 후 진공 층착기로 기판을 이송하였다.Glass substrate coated with ITO (Indium tin oxide) thin film with thickness of 1500 Å was washed with distilled water ultrasonic wave. After the distilled water was washed, it was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, and methanol, and dried. Then, the substrate was transferred to a UV OZONE cleaner (Power Sonic 405, Hoshin Tech), and the substrate was cleaned using UV for 5 minutes And the substrate was transferred to the back vacuum deposition machine.
상기와 같이 준비된 ITO 투명 전극 위에 m-MTDATA(60nm)/합성예 1에서 합성된 화합물 A-1 (80nm)/DS-H522 + 5% DS-501(300nm)/BCP(10nm)/Alq3(30 nm)/LiF(1nm)/Al(200nm) 순서로 유기 EL 소자를 제조하였다. (60 nm) / Compound A-1 (80 nm) / DS-H522 + 5% DS-501 (300 nm) / BCP (10 nm) / Alq3 (60 nm) synthesized in Synthesis Example 1 nm) / LiF (1 nm) / Al (200 nm).
소자 제작에 사용된 DS-H522 및 DS-501은 ㈜두산 전자 BG의 제품이며, m-MTDATA, TCTA, CBP, Ir(ppy)3, 및 BCP의 구조는 하기와 같다.The structures of m-MTDATA, TCTA, CBP, Ir (ppy) 3 and BCP are as follows. DS-H522 and DS-501 used in the device fabrication are products of Doosan Electronics BG.
[실시예 2 ~ 76] 유기 EL 소자의 제조[Examples 2 to 76] Preparation of organic EL device
실시예 1에서 정공 수송층 형성시 정공 수송층 물질로 사용된 화합물 A-1 대신 합성예 2 내지 76에서 각각 합성된 화합물을 사용하는 것을 제외하고는, 실시예 1과 동일하게 수행하여 유기 EL 소자를 제조하였다.
An organic EL device was manufactured in the same manner as in Example 1 except that the compound synthesized in each of Synthesis Examples 2 to 76 was used instead of Compound A-1 used as a hole transporting layer material in the formation of the hole transport layer in Example 1 Respectively.
[비교예 1] 유기 EL 소자의 제작[Comparative Example 1] Fabrication of organic EL device
실시예 1에서 정공 수송층 형성시 정공 수송층 물질로 사용된 화합물 A-1 대신 NPB를 정공수송층 물질로 사용한 것을 제외하고는, 상기 실시예 1과 동일한 방법으로 유기 EL 소자를 제조하였다. 사용된 NPB의 구조는 하기와 같다.An organic EL device was prepared in the same manner as in Example 1 except that NPB was used as the hole transport layer material instead of the compound A-1 used as the hole transport layer material in forming the hole transport layer in Example 1. The structure of the NPB used is as follows.
[평가예 1][Evaluation Example 1]
실시예 1 내지 76, 및 비교예 1에서 각각 제조된 유기 EL 소자에 대하여 전류밀도 10 mA/㎠에서의 구동전압 및 전류효율를 측정하였고, 그 결과를 하기 표 1에 나타내었다.The driving voltage and current efficiency at the current density of 10 mA / cm 2 were measured for the organic EL devices manufactured in Examples 1 to 76 and Comparative Example 1, respectively, and the results are shown in Table 1 below.
상기 표 1에 나타낸 바와 같이, 본 발명에 따른 화합물을 정공수송층으로 사용한 실시예 1~76의 유기 EL 소자는, 종래 NPB를 사용한 비교예 1의 유기 EL 소자에 비해 전류효율 및 구동전압 면에서 보다 우수한 성능을 나타내는 것을 알 수 있었다.
As shown in Table 1, the organic EL devices of Examples 1 to 76 using the compound according to the present invention as a hole transporting layer were superior in current efficiency and driving voltage to organic EL devices of Comparative Example 1 using NPB It was found that it exhibits excellent performance.
[실시예 77] 녹색 유기 전계 발광 소자의 제조[Example 77] Production of green organic electroluminescent device
합성예 1에서 합성된 화합물 1을 통상적으로 알려진 방법으로 고순도 승화정제를 한 후, 하기와 같이 녹색 유기 전계 발광 소자를 제조하였다.Compound 1 synthesized in Synthesis Example 1 was subjected to high purity sublimation purification by a conventionally known method, and then a green organic electroluminescent device was produced as follows.
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.The glass substrate coated with ITO (Indium tin oxide) thin film with thickness of 1500 Å was washed with distilled water ultrasonic wave. After the distilled water was washed, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, and dried. Then, the substrate was transferred to a UV OZONE cleaner (Power sonic 405, Hoshin Tech) And the substrate was transferred to a vacuum evaporator.
상기와 같이 준비된 ITO 투명 전극 위에, m-MTDATA (60 nm)/TCTA (80 nm)/화합물 A-1(40nm)/CBP + 10 % Ir(ppy)3 (300nm)/BCP (10 nm)/Alq3 (30 nm)/LiF (1 nm)/Al (200 nm) 순으로 적층하여 유기 전계 발광 소자를 제조하였다.(60 nm) / TCTA (80 nm) / Compound A-1 (40 nm) / CBP + 10% Ir (ppy) 3 (300 nm) / BCP (10 nm) / Alq3 (30 nm) / LiF (1 nm) / Al (200 nm) were stacked in this order to produce an organic electroluminescent device.
사용된 m-MTDATA, TCTA, Ir(ppy)3, CBP 및 BCP의 구조는 하기와 같다.The structures of m-MTDATA, TCTA, Ir (ppy) 3, CBP and BCP used are as follows.
[실시예 78 ~ 152] 녹색 유기 전계 발광 소자의 제조[Examples 78 to 152] Preparation of green organic electroluminescent device
실시예 77에서 A-1 대신 합성예 1 내지 76 에서 각각 합성된 화합물을 사용하는 것을 제외하고는, 실시예 77과 동일하게 수행하여 유기 EL 소자를 제조하였다.
An organic EL device was fabricated in the same manner as in Example 77 except that the compound synthesized in each of Synthesis Examples 1 to 76 was used instead of A-1 in Example 77. [
[비교예 2] 녹색 유기 전계 발광 소자의 제조[Comparative Example 2] Production of green organic electroluminescent device
실시예 77에서 화합물 A-1을 사용하지 않은 것을 제외하고는, 실시예 77과 동일하게 수행하여 녹색 유기 전계 발광 소자를 제조하였다.
A green organic electroluminescent device was fabricated in the same manner as in Example 77 except that the compound A-1 was not used in Example 77. As a result,
[평가예 2][Evaluation Example 2]
실시예 77 내지 152, 및 비교예 2에서 각각 제조된 유기 전계 발광 소자에 대하여, 전류밀도 10 mA/㎠에서의 구동전압, 전류효율 및 발광 피크를 측정하고, 그 결과를 하기 표 2에 나타내었다.The driving voltage, current efficiency and emission peak at current densities of 10 mA / cm 2 were measured for the organic electroluminescent devices manufactured in Examples 77 to 152 and Comparative Example 2, respectively, and the results are shown in Table 2 below .
상기 표 2 에 나타낸 바와 같이, 본 발명에 따른 화학식 1로 표시되는 화합물을 발광 재료로 사용한 실시예 77~152의 녹색 유기 전계 발광 소자는, 종래 CBP만을 발광층의 재료로 사용한 비교예 2의 녹색 유기 전계 발광 소자에 비해 전류효율 및 구동전압 면에서 보다 우수한 성능을 나타내는 것을 알 수 있었다.
As shown in Table 2, the green organic electroluminescent devices of Examples 77 to 152, in which the compound represented by Formula 1 according to the present invention was used as a light emitting material, It was found that the current efficiency and the driving voltage were superior to those of the electroluminescent device.
[실시예 153 ~ 228] 적색 유기 전계 발광 소자의 제조[Examples 153 to 228] Preparation of red organic electroluminescent device
합성예에서 합성한 화합물을 통상적으로 알려진 방법으로 고순도 승화정제를 한 후 아래의 과정에 따라 적색 유기 전계 발광 소자를 제작하였다.The compound synthesized in Synthesis Example was subjected to high purity sublimation purification by a conventionally known method, and a red organic electroluminescent device was fabricated according to the following procedure.
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 ITO (Indium Tin Oxide) with a thickness of 1500 Å was washed with distilled water ultrasonic waves. After the distilled water was washed, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, dried and transferred to a UV OZONE cleaner (Power Sonic 405, Hoshin Tech), the substrate was cleaned using UV for 5 minutes, The substrate was transferred.
상기와 같이 준비된 ITO 투명 전극 위에, m-MTDATA (60 nm)/TCTA (80 nm)/합성예 1 내지 76 (40nm)/CBP + 10 % (piq)2Ir(acac) (300nm)/BCP (10 nm)/Alq3 (30 nm)/LiF (1 nm)/Al (200 nm) 순으로 적층하여 유기 전계 발광 소자를 제조하였다.(60 nm) / TCTA (80 nm) / Synthesis Examples 1 to 76 (40 nm) / CBP + 10% (piq) 2 Ir (acac) (300 nm) / BCP (10 nm) on the ITO transparent electrode prepared as described above nm) / Alq3 (30 nm) / LiF (1 nm) / Al (200 nm) were stacked in this order to fabricate an organic electroluminescent device.
사용된 m-MTDATA, TCTA, (piq)2Ir(acac) 및 CBP의 구조는 하기와 같다.The structures of m-MTDATA, TCTA, (piq) 2Ir (acac) and CBP used are as follows.
[비교예 3] 적색 유기 전계 발광 소자의 제작[Comparative Example 3] Production of red organic electroluminescent device
실시예 153 에서 화합물 A-1을 사용하지 않은 것을 제외하고는, 실시예 153과 동일하게 수행하여 적색 유기 전계 발광 소자를 제조하였다. A red organic electroluminescent device was fabricated in the same manner as in Example 153 except that the compound A-1 was not used in Example 153.
상기 표 3 에 나타낸 바와 같이, 본 발명에 따른 화학식 1로 표시되는 화합물을 발광 재료로 사용한 실시예 153~228의 적색 유기 전계 발광 소자는, 종래 CBP만을 발광층의 재료로 사용한 비교예 3의 적색 유기 전계 발광 소자에 비해 전류효율 및 구동전압 면에서 보다 우수한 성능을 나타내는 것을 알 수 있었다.
As shown in Table 3, the red organic electroluminescent devices of Examples 153 to 228, in which the compound represented by Formula 1 according to the present invention was used as a light emitting material, It was found that the current efficiency and the driving voltage were superior to those of the electroluminescent device.
[실시예 229 ~ 304] 청색 유기 전계 발광 소자의 제조[Examples 229 to 304] Preparation of blue organic electroluminescent device
합성예에서 합성한 화합물을 통상적으로 알려진 방법으로 고순도 승화정제를 한 후 아래의 과정에 따라 적색 유기 전계 발광 소자를 제작하였다.The compound synthesized in Synthesis Example was subjected to high purity sublimation purification by a conventionally known method, and a red organic electroluminescent device was fabricated according to the following procedure.
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 ITO (Indium Tin Oxide) with a thickness of 1500 Å was washed with distilled water ultrasonic waves. After the distilled water was washed, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, dried and transferred to a UV OZONE cleaner (Power Sonic 405, Hoshin Tech), the substrate was cleaned using UV for 5 minutes, The substrate was transferred.
상기와 같이 준비된 ITO 투명 전극 위에, DS-205 (두산社) (80 nm)/NPB (15 nm)/합성예 1 내지 76의 각각의 화합물(15nm)/ADN + 5 % DS-405 (두산社) (300nm)/BCP (10 nm)/Alq3 (30 nm)/LiF (1 nm)/Al (200 nm) 순으로 적층하여 유기 전계 발광 소자를 제조하였다.Each of the compounds (15 nm) / ADN + 5% DS-405 (manufactured by Doosan Heavy Industries, Ltd.) of DS-205 (Doosan) (80 nm) / NPB (300 nm) / BCP (10 nm) / Alq3 (30 nm) / LiF (1 nm) / Al (200 nm) were stacked in this order to produce an organic electroluminescent device.
사용된 ADN의 구조는 하기와 같다.The structure of the ADN used is as follows.
[비교예 4] 청색 유기 전계 발광 소자의 제작[Comparative Example 4] Fabrication of blue organic electroluminescent device
실시예 229에서 A-1을 사용하지 않은 것을 제외하고는, 실시예 229와 동일하게 수행하여 청색 유기 전계 발광 소자를 제조하였다.
A blue organic electroluminescent device was fabricated in the same manner as in Example 229 except that A-1 was not used in Example 229.
[평가예 4][Evaluation Example 4]
실시예 229 ~ 304 및 비교예 4 에서 제작한 각각의 청색 유기 전계 발광 소자에 대하여 전류밀도 10 mA/㎠에서의 구동전압 및 전류효율을 측정하고, 그 결과를 하기 표 4에 나타내었다.The driving voltage and the current efficiency at the current density of 10 mA / cm 2 were measured for each of the blue organic electroluminescent devices manufactured in Examples 229 to 304 and Comparative Example 4. The results are shown in Table 4 below.
상기 표 4 에 나타낸 바와 같이, 본 발명에 따른 화학식 1로 표시되는 화합물을 발광 재료로 사용한 실시예 229~304의 청색 유기 전계 발광 소자는, 종래의 비교예 4의 청색 유기 전계 발광 소자에 비해 전류효율 및 구동전압 면에서 보다 우수한 성능을 나타내는 것을 알 수 있었다.As shown in Table 4, the blue organic electroluminescent devices of Examples 229 to 304, in which the compound represented by Formula 1 according to the present invention was used as a light emitting material, It was found that the device exhibited better performance in terms of efficiency and driving voltage.
이상을 통해 본 발명의 바람직한 실시예에 대하여 설명하였지만, 본 발명은 이에 한정되는 것이 아니고 특허청구범위와 발명의 상세한 설명의 범위 안에서 여러 가지로 변형하여 실시하는 것이 가능하고 이 또한 발명의 범주에 속하는 것은 당연하다.While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it is to be understood that the invention is not limited to the disclosed embodiments, but, on the contrary, It is natural.
Claims (6)
[화학식 1]
상기 화학식 1에서,
Ar1 은 하기 화학식 2로 표시되는 치환기이고,
[화학식 2]
Ar2 내지 Ar4 는 서로 동일하거나 또는 상이하며, 각각 독립적으로 치환 또는 비치환된 C6~C60의 아릴기, 치환 또는 비치환된 핵원자수 5 내지 60의 헤테로아릴기 및 치환 또는 비치환된 C6~C60의 아릴아민기에서 선택되고,
단, Ar2 및 Ar3 중 적어도 하나는 하기 화학식 3으로 표시되는 치환기이며;
[화학식 3]
상기 화학식 2 내지 화학식 3에서,
*는 결합이 이루어지는 부위이고;
R1은 서로 동일하거나 또는 상이하며, 각각 독립적으로 수소, 중수소, 각각 독립적으로 치환 또는 비치환된 C1~C40의 알킬기, 치환 또는 비치환된 C6~C60의 아릴기, 치환 또는 비치환된 핵원자수 5 내지 60의 헤테로아릴기, 및 치환 또는 비치환된 C6~C60의 아릴아민기로 이루어진 군에서 선택되고, 또는 이들은 인접하는 치환기와 결합하여 축합 방향족환 또는 축합 헤테로방향족환을 형성할 수 있으며;
R2는 서로 동일하거나 또는 상이하며, 각각 독립적으로 치환 또는 비치환된 C1~C40의 알킬기, 및 치환 또는 비치환된 C6~C60의 아릴기로 이루어진 군에서 선택되고,
n, m, l은 각각 독립적으로 1 내지 3의 정수이고;
a, b, c, d, e, f, g는 각각 독립적으로 0 내지 4의 정수이다.
상기 알킬기, 아릴기, 헤테로아릴기 및 아릴아민기가 치환될 경우는, 각각 독립적으로 중수소, 할로겐, 시아노, C1~C40의 알킬기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 구성된 군으로부터 선택되는 1종 이상으로 치환될 수 있다.A compound represented by the following formula (1):
[Chemical Formula 1]
In Formula 1,
Ar 1 is a substituent represented by the following formula (2)
(2)
Ar 2 to Ar 4 are the same or different and each independently represents a substituted or unsubstituted C 6 to C 60 aryl group, a substituted or unsubstituted heteroaryl group having 5 to 60 ring atoms, C 6 to C 60 arylamine groups,
Provided that at least one of Ar 2 and Ar 3 is a substituent represented by the following formula (3);
(3)
In the above Chemical Formulas 2 to 3,
* Is the site where the bond is made;
R 1 are the same or different and are each independently hydrogen, deuterium, a substituted or unsubstituted C 1 to C 40 alkyl group, a substituted or unsubstituted C 6 to C 60 aryl group, A heteroaryl group having 5 to 60 ring atoms and a substituted or unsubstituted C 6 to C 60 arylamine group, or they may be bonded to adjacent substituents to form a condensed aromatic ring or condensed heteroaromatic ring ≪ / RTI >
R 2 is the same or different and is independently selected from the group consisting of a substituted or unsubstituted C 1 to C 40 alkyl group and a substituted or unsubstituted C 6 to C 60 aryl group,
n, m and l are each independently an integer of 1 to 3;
a, b, c, d, e, f and g are each independently an integer of 0 to 4;
When the alkyl group, an aryl group, a heteroaryl group and an arylamine group is substituted, each independently represent deuterium, halogen, cyano, C 1 ~ C 40 alkyl group, C 3 ~ C 40 cycloalkyl group, the number of nuclear atoms of 3 to the A C 6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 to C 40 alkyloxy group, a C 6 to C 60 aryloxy group, a C 3 to C 6 heteroaryl group, 40 alkylsilyl group, C 6 ~ C 60 aryl silyl group, C 1 ~ C 40 group of an alkyl boron, C 6 ~ C group 60 arylboronic of, C 6 ~ aryl phosphine of C 60 pingi, C 6 ~ C 60 aryl phosphine which may be substituted with oxide groups and at least one member selected from the group consisting of an aryl amine of the C 6 ~ C 60 of.
상기 화학식 1로 표시되는 화합물은 하기 화학식 4 또는 화학식 5 로 표시되는 것을 특징으로 하는 화합물:
[화학식 4]
[화학식 5]
상기 식에서, Ar2 ~ Ar4, R1~R2, a~g는 각각 제1항에서 정의된 바와 같다.The method according to claim 1,
The compound represented by the formula (1) is represented by the following formula (4) or (5):
[Chemical Formula 4]
[Chemical Formula 5]
Wherein Ar 2 to Ar 4 , R 1 to R 2 , and a to g are as defined in claim 1, respectively.
화학식 3을 갖지 않는 Ar2 내지 Ar4는 서로 동일하거나 또는 상이하며, 각각 독립적으로 치환 또는 비치환된 C6~C60의 아릴기이거나 또는, 치환 또는 비치환된 핵원자수 5 내지 60의 헤테로아릴기인 것을 특징으로 하는 화합물. The method according to claim 1,
Ar 2 to Ar 4 which do not have the general formula (3) are the same or different and are each independently a substituted or unsubstituted C 6 to C 60 aryl group or a substituted or unsubstituted heteroaromatic having 5 to 60 Lt; / RTI > is an aryl group.
R1는 서로 동일하거나 또는 상이하며, 각각 독립적으로 수소, 치환 또는 비치환된 C6~C60의 아릴기이거나 또는, 치환 또는 비치환된 핵원자수 5 내지 60의 헤테로아릴기이며,
R2는 서로 동일하거나 또는 상이하며, 각각 독립적으로 메틸기, 페닐기, 인 것을 특징으로 하는 화합물.The method according to claim 1,
R 1 is the same or different and is each independently hydrogen, a substituted or unsubstituted C 6 -C 60 aryl group, or a substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms,
R 2 are the same or different and each independently represents a methyl group, a phenyl group, ≪ / RTI >
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