KR20180065193A - Organic compound and organic electroluminescent device using the same - Google Patents
Organic compound and organic electroluminescent device using the same Download PDFInfo
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- KR20180065193A KR20180065193A KR1020160165709A KR20160165709A KR20180065193A KR 20180065193 A KR20180065193 A KR 20180065193A KR 1020160165709 A KR1020160165709 A KR 1020160165709A KR 20160165709 A KR20160165709 A KR 20160165709A KR 20180065193 A KR20180065193 A KR 20180065193A
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 12
- 239000012044 organic layer Substances 0.000 claims description 98
- 150000001875 compounds Chemical class 0.000 claims description 84
- 239000010410 layer Substances 0.000 claims description 53
- 125000003118 aryl group Chemical group 0.000 claims description 30
- 229910052757 nitrogen Inorganic materials 0.000 claims description 21
- 125000004429 atom Chemical group 0.000 claims description 20
- -1 diaryl phosphine Chemical compound 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000004104 aryloxy group Chemical group 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 125000005104 aryl silyl group Chemical group 0.000 claims description 9
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 7
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 6
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 6
- 125000005264 aryl amine group Chemical group 0.000 claims description 6
- 125000000732 arylene group Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 229910052805 deuterium Inorganic materials 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000005549 heteroarylene group Chemical group 0.000 claims description 6
- GKTNLYAAZKKMTQ-UHFFFAOYSA-N n-[bis(dimethylamino)phosphinimyl]-n-methylmethanamine Chemical group CN(C)P(=N)(N(C)C)N(C)C GKTNLYAAZKKMTQ-UHFFFAOYSA-N 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 229910052796 boron Inorganic materials 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 4
- 150000004982 aromatic amines Chemical class 0.000 claims description 4
- 239000008280 blood Substances 0.000 claims description 4
- 210000004369 blood Anatomy 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 20
- 239000011368 organic material Substances 0.000 abstract description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 192
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 189
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 72
- 230000015572 biosynthetic process Effects 0.000 description 67
- 238000003786 synthesis reaction Methods 0.000 description 67
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 65
- 238000006243 chemical reaction Methods 0.000 description 63
- 238000004440 column chromatography Methods 0.000 description 63
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 62
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 56
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 48
- 239000000203 mixture Substances 0.000 description 41
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 30
- 239000012299 nitrogen atmosphere Substances 0.000 description 29
- 229910000027 potassium carbonate Inorganic materials 0.000 description 28
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical group C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 26
- 239000002904 solvent Substances 0.000 description 22
- 238000002360 preparation method Methods 0.000 description 18
- 239000000243 solution Substances 0.000 description 12
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 11
- 238000005160 1H NMR spectroscopy Methods 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- KPNTTXKVLWHMQD-UHFFFAOYSA-N (1,1-dimethylinden-5-yl)boronic acid Chemical compound CC1(C=CC2=CC(=CC=C12)B(O)O)C KPNTTXKVLWHMQD-UHFFFAOYSA-N 0.000 description 9
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 9
- WYXQQAYIAJRORT-UHFFFAOYSA-N 1-benzofuran-5-ylboronic acid Chemical compound OB(O)C1=CC=C2OC=CC2=C1 WYXQQAYIAJRORT-UHFFFAOYSA-N 0.000 description 8
- 125000000524 functional group Chemical group 0.000 description 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 7
- UHCYUVNJVPRFGF-UHFFFAOYSA-N 4-(3,5-dibromophenyl)-2-phenyl-6-(4-phenylphenyl)pyrimidine Chemical compound BrC1=CC(Br)=CC(C=2N=C(N=C(C=2)C=2C=CC(=CC=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 UHCYUVNJVPRFGF-UHFFFAOYSA-N 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 4
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 125000006575 electron-withdrawing group Chemical group 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 229960005235 piperonyl butoxide Drugs 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 239000012964 benzotriazole Substances 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
- 125000005647 linker group Chemical group 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- DRQMSTXYCLCAHO-UHFFFAOYSA-N 2-(3,5-dibromophenyl)-4,6-diphenyl-1,3,5-triazine Chemical compound BrC1=CC(Br)=CC(C=2N=C(N=C(N=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 DRQMSTXYCLCAHO-UHFFFAOYSA-N 0.000 description 2
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 2
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
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- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 230000000903 blocking effect Effects 0.000 description 2
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- 238000011161 development Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 239000011669 selenium Substances 0.000 description 2
- 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 2
- 239000011787 zinc oxide Substances 0.000 description 2
- 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 1
- 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 1
- KRVWTVYQGIOXQE-UHFFFAOYSA-N 1-(2,6-diphenoxyphenoxy)naphthalene Chemical group C=1C=CC(OC=2C=CC=CC=2)=C(OC=2C3=CC=CC=C3C=CC=2)C=1OC1=CC=CC=C1 KRVWTVYQGIOXQE-UHFFFAOYSA-N 0.000 description 1
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 1
- HTFNVAVTYILUCF-UHFFFAOYSA-N 2-[2-ethoxy-4-[4-(4-methylpiperazin-1-yl)piperidine-1-carbonyl]anilino]-5-methyl-11-methylsulfonylpyrimido[4,5-b][1,4]benzodiazepin-6-one Chemical compound CCOc1cc(ccc1Nc1ncc2N(C)C(=O)c3ccccc3N(c2n1)S(C)(=O)=O)C(=O)N1CCC(CC1)N1CCN(C)CC1 HTFNVAVTYILUCF-UHFFFAOYSA-N 0.000 description 1
- UOXJNGFFPMOZDM-UHFFFAOYSA-N 2-[di(propan-2-yl)amino]ethylsulfanyl-methylphosphinic acid Chemical compound CC(C)N(C(C)C)CCSP(C)(O)=O UOXJNGFFPMOZDM-UHFFFAOYSA-N 0.000 description 1
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- 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 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
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- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
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- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
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- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
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- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
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- 239000002253 acid Substances 0.000 description 1
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 1
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- 125000001931 aliphatic group Chemical group 0.000 description 1
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- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 229920000123 polythiophene Polymers 0.000 description 1
- 239000007774 positive electrode material Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 229910052719 titanium Inorganic materials 0.000 description 1
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- 125000004306 triazinyl group Chemical group 0.000 description 1
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- 238000001771 vacuum deposition Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- H01L51/0071—
-
- H01L51/0073—
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- H01L51/5072—
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- H01L51/5092—
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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
- H10K50/16—Electron transporting 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]
- H10K50/17—Carrier injection layers
- H10K50/171—Electron injection layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
Abstract
Description
본 발명은 신규한 유기 화합물 및 이를 이용한 유기 전계 발광 소자에 관한 것으로, 보다 구체적으로는 전자 수송능 등이 우수한 신규 유기 화합물 및 상기 화합물을 유기물층의 재료로서 포함하여 발광효율, 구동전압, 수명 등의 특성이 향상된 유기 전계 발광 소자에 관한 것이다.[0001] The present invention relates to a novel organic compound and an organic electroluminescent device using the same. More specifically, the present invention relates to a novel organic compound having excellent electron transport ability and the like, And an organic electroluminescent device having improved characteristics.
1965년 안트라센 단결정을 이용한 청색 전기발광으로 이어진 유기 전계발광(electroluminescent, EL) 소자(이하, 간단히 '유기 EL 소자'로 칭함)에 대한 연구가 이어져 오다가, 1987년 탕(Tang)에 의하여 정공층(NPB)과 발광층(Alq3)으로 구성된 2층 적층구조의 유기 EL소자가 제안되었다. 이후 유기 EL 소자는 상용화를 위해 필요한 고효율, 장수명 특성을 구현하기 위하여, 소자 내에 정공주입, 수송을 담당하는 유기층과 전자주입, 수송을 담당하는 유기층, 정공과 전자의 결합에 의해 전계 발광이 일어나도록 유도하는 유기층 등과 같이 각각의 특징적이고, 세분화된 기능을 부여한 다층 적층구조의 형태가 제안되었다. 다층 적층구조의 도입은 유기 EL 소자의 성능을 상용화 특성까지 향상시켜, 1997년 차량용 라디오 디스플레이 제품을 시작으로 휴대용 정보표시기기 및 TV용 디스플레이 소자로까지 그 적용 범위를 확대시키려 하고 있다.In 1965, research on organic electroluminescent (EL) devices (hereinafter, simply referred to as 'organic EL devices') which resulted in blue electroluminescence using anthracene single crystals was carried on. In 1987, (NPB) and a light-emitting layer (Alq 3 ). In order to realize the high efficiency and long life characteristics required for commercialization, the organic EL device is required to have an organic layer for injecting and transporting holes, an organic layer for electron injection and transportation, and an organic layer for transporting light. And organic layers such as an organic layer which induces a specific function, and a multi-layer laminated structure in which functionalities are finely divided are provided. The introduction of the multi-layer laminated structure improves the performance of the organic EL device to commercialization characteristics, and the application range from the car radio display product to the portable information display device and the TV display device is expanded in 1997.
디스플레이의 대형화, 고해상도화의 요구는 유기 EL 소자의 고효율화, 장수명화의 과제를 부여하고 있다. 효율과 수명, 구동전압 등은 서로 연관이 있으며, 효율이 증가되면 상대적으로 구동전압이 떨어지고, 구동전압이 떨어지면서 구동 시 발생하는 주울열(Joule heating)에 의한 유기물질의 결정화가 적어져 결과적으로 수명이 높아지는 경향을 나타낸다. 하지만 상기 유기물층을 단순히 개선한다고 하여 효율을 극대화시킬 수는 없다. 왜냐하면 각 유기물층 간의 에너지 준위(energy level) 및 T1 값, 물질의 고유특성(이동도(mobility), 계면특성 등) 등이 최적의 조합을 이루었을 때 긴 수명과 높은 효율을 동시에 달성할 수 있기 때문이다.The demand for a larger display and a higher resolution of a display has given the problem of high efficiency and long life of an organic EL device. The efficiency, lifetime, and driving voltage are related to each other. As the efficiency increases, the driving voltage decreases. As the driving voltage decreases, the crystallization of the organic material due to Joule heating, which occurs during driving, And the lifetime tends to increase. However, simply improving the organic material layer can not maximize the efficiency. This is because when the optimal combination of the energy level and T1 value of each organic material layer, the intrinsic properties (mobility, interfacial properties, etc.) of the material, etc. are achieved, long life and high efficiency can be achieved at the same time to be.
일반적으로 전자수송층에서 발광층으로 전자(electron)가 전달되고 정공(hole)이 정공수송층에서 발광층으로 전달되어 재조합(recombination)에 의해 엑시톤(exciton)이 생성된다. 하지만 정공이 전자보다 빠르게 이동되어 발광층 내에서 생성된 엑시톤이 전자수송층으로 넘어가게 되어 결과적으로 발광층 내 전하불균형(charge unbalance)을 초래하여 전자수송층 계면에서 발광하게 된다. 전자수송층 계면에서 발광될 경우, 유기 EL 소자의 색순도 및 효율이 저하되는 문제점이 발생되고 있으며, 특히 유기 EL 소자 제작 시 고온 안정성이 떨어져 유기 EL 소자의 수명이 짧아지는 문제점이 발생하게 된다. 따라서 고온안정성과 높은 T1 값을 가지며 전자이동도가 빠르고 효과적인 정공저지능력 (hole blocking ability)을 갖는 전자수송 물질의 개발이 필요한 시점이다. Generally, electrons are transferred from the electron transport layer to the light emitting layer, and holes are transferred from the hole transport layer to the light emitting layer to generate excitons by recombination. However, the holes move faster than the electrons, so that the excitons generated in the light emitting layer are transferred to the electron transporting layer, resulting in charge unbalance in the light emitting layer and light emission at the interface of the electron transporting layer. When light is emitted from the interface of the electron transport layer, the color purity and efficiency of the organic EL device are deteriorated. In particular, the organic EL device has a problem in that the lifetime of the organic EL device is shortened due to low temperature stability. Therefore, it is necessary to develop an electron transporting material having high temperature stability, high T1 value, fast electron mobility and effective hole blocking ability.
즉, 유기전기 발광소자가 갖는 우수한 특징들을 충분히 발휘하기 위해서는 소자 내 유기물층을 이루는 물질, 예컨대 정공주입 물질, 정공수송 물질, 발광 물질, 전자수송 물질, 전자주입 물질, 발광보조층 물질 등이 안정하고 효율적인 재료에 의하여 뒷받침되는 것이 선행되어야 하나, 아직까지 안정되고 효율적인 유기전기 발광소자용 유기물층 재료의 개발이 충분히 이루어지지 않은 상태이다. 따라서, 새로운 재료의 개발이 계속 요구되고 있으며, 특히 정공수송층, 전자수송층 등의 재료 조합에 대한 개발이 절실히 요구되고 있다.That is, in order to sufficiently exhibit the excellent characteristics of the organic electroluminescent device, materials constituting the organic material layer in the device such as a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, an electron injecting material, The organic material layer for an organic electroluminescence device has not yet been developed sufficiently. Therefore, development of new materials is continuously required, and development of a combination of materials such as a hole transporting layer, an electron transporting layer, and the like is urgently required.
본 발명은 전자 수송능, 전자 주입능 등이 우수하여 유기물층 재료로 사용될 수 있는 신규 유기 화합물을 제공하는 것을 목적으로 한다.An object of the present invention is to provide a novel organic compound which is excellent in electron transporting ability and electron injecting ability and can be used as an organic material layer material.
또한, 본 발명은 상기 신규 유기 화합물을 포함하여 구동전압이 낮고, 발광효율이 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 novel organic compound, which has low driving voltage, high luminous efficiency, and improved lifetime.
상기 목적을 달성하기 위하여, 본 발명의 일례는 하기 화학식 1로 표시되는 화합물을 제공한다.In order to accomplish the above object, an example of the present invention provides a compound represented by the following general formula (1).
상기 화학식 1에서,In Formula 1,
X1 내지 X6 은 각각 서로 동일하거나 상이하며, C, N 중 하나의 원자를 함유하고,X 1 to X 6 are the same or different from each other and contain one atom of C and N,
A와 B는 각각 서로 동일하거나 상이하며, 독립적으로 하기 화학식 2 또는 화학식 3으로 표시될 수 있고A and B are the same or different from each other and independently can be represented by the following formula (2) or (3)
상기 화학식 2 또는 화학식 3에서,In Formula 2 or Formula 3,
X7 내지 X9 은 각각 서로 동일하거나 상이하며, S, O, N(Ar1), C(Ar2)(Ar3) 중 어느 하나의 원자를 함유하고,X 7 to X 9 are the same or different from each other and contain any one of S, O, N (Ar 1 ) and C (Ar 2 ) (Ar 3 )
n은 0 내지 4의 정수이며,n is an integer of 0 to 4,
C는 하기 화학식 4 로 표현되는 치환기이고,C is a substituent represented by the following formula (4)
상기 화학식 4에서,In Formula 4,
*은 X1 내지 X6 와 결합이 이루어지는 부분을 의미하고;* Represents a moiety in which X 1 to X 6 are bonded;
L1은 단일결합, C6~C18의 아릴렌기 및 핵원자수 5 내지 18개의 헤테로아릴렌기로 이루어진 군에서 선택되며;L 1 is selected from the group consisting of a single bond, a C 6 to C 18 arylene group and a heteroarylene group having 5 to 18 nuclear atoms;
R1 내지 R3와 Ar1 내지 Ar3은 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성하며;R 1 to R 3 and Ar 1 to Ar 3 are each independently selected from hydrogen, deuterium, halogen, cyano, nitro, C 1 to C 40 alkyl, C 2 to C 40 alkenyl, C 2 to C 40 alkynyl, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 6 ~ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 1 ~ alkyloxy group of C 40, A C 6 to C 60 aryloxy group, a C 3 to C 40 alkylsilyl group, a C 6 to C 60 arylsilyl group, a C 1 to C 40 alkylboron group, a C 6 to C 60 arylboron group, C 6 ~ C 60 aryl phosphazene group, C 6 ~ C 60 mono or diaryl phosphine blood group and a C 6 ~, or selected from the group consisting of an aryl amine of the C 60, the combined group adjacent to form a condensed ring ;
상기 L1의 아릴렌기 및 헤테로아릴렌기와, 상기 R1 내지 R3와 Ar1 내지 Ar3의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다.Arylene group and a heteroarylene group, an alkyl group of the R 1 to R 3 and Ar 1 to Ar 3 of the L 1, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group , A heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkylboron group, an arylboron group, an arylphosphonyl group, a mono- or diarylphosphinyl group, and an arylsilyl group are each independently selected from deuterium, halogen, cyano, nitro, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, an alkynyl group of C 2 ~ C 40, C 6 ~ aryl group of C 60, nuclear atoms of 5 to 60 heteroaryl group, C 6 ~ C aryloxy 60, C 1 ~ C 40 alkyloxy group of, C 6 ~ C 60 aryl amine group, C 3 ~ cycloalkyl group of C 40, nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkylsilyl group, C 1 ~ C 40 alkyl group of boron, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 aryl phosphazene group, C 6 ~ C 60 mono- or dia rilpo of If blood group and a C 6 ~ substituted by one or more substituents selected from the group consisting of C 60 or silyl aryl is unsubstituted, substituted by a plurality of substituents, they may be the same or different from each other.
또한, 본 발명의 다른 일례는 양극, 음극 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하는 유기 전계 발광 소자로서, 상기 1층 이상의 유기물층 중에서 적어도 하나는 전술한 화학식 1로 표시되는 화합물을 포함하는 유기 전계 발광 소자를 제공한다.Another example of the present invention is an organic electroluminescent device comprising a cathode, a cathode, and at least one organic layer sandwiched between the anode and the cathode, wherein at least one of the one or more organic layers is a compound represented by the general formula An organic electroluminescent device comprising a compound to be displayed is provided.
본 발명의 일례에 따른 화학식 1로 표시되는 화합물은 내열성, 전자 주입능, 전자 수송능 등이 우수하기 때문에, 유기 전계 발광 소자의 유기물층 재료, 바람직하게는 전자 주입층 재료, 또는 전자 수송층 재료로 사용될 수 있다.The compound represented by the formula (1) according to an embodiment of the present invention is excellent in heat resistance, electron injecting ability, electron transporting ability, and the like, and therefore can be used as an organic layer material of an organic electroluminescent device, preferably an electron injecting layer material or an electron transporting layer material .
또한, 본 발명의 일례에 따른 화합물을 전자 주입층 또는 전자 수송층에 포함하는 유기 전계 발광 소자는 구동전압, 효율, 수명등의 측면이 크게 향상될 수 있고, 이러한 유기 전계 발광 소자는 풀 칼라 디스플레이 패널 등에 효과적으로 적용될 수 있다.In addition, the organic electroluminescent device including the compound according to an example of the present invention in the electron injection layer or the electron transport layer can greatly improve the driving voltage, efficiency, and life, and the organic electroluminescent device can be applied to a full color display panel And the like.
이하, 본 발명을 상세히 설명한다.Hereinafter, the present invention will be described in detail.
1. 유기 화합물1. Organic compounds
본 발명의 유기 화합물은 두 개 이상의 5원 방향족 고리 또는 5원 방향족 헤테로 고리를 포함하는 치환기가 결합된 모이어티에, 한 개 이상의 치환기가 직접 또는 링커기를 통해 연결된 구조를 기본 골격으로 가지는 화합물로, 상기 화학식 1로 표시된다.The organic compound of the present invention is a compound having, as a basic skeleton, a structure in which one or more substituents are directly or through a linker group to a moiety having a substituent bonded thereto containing two or more 5-membered aromatic rings or 5-membered aromatic heterocyclic rings, (1).
이때, 5원 방향족 고리 또는 5원 방향족 헤테로 고리를 포함하는 치환기는 벤조헤테로펜타곤(benzoheteropentagon) 화합물로, 예컨대 벤조트리아졸(benzotriazole), 인다졸(indazole), 인덴(indene), 벤조퓨란(benzofuran) 등일 수 있다.Here, the substituent containing a 5-membered aromatic ring or a 5-membered aromatic heterocycle is a benzoheteropentagon compound such as benzotriazole, indazole, indene, benzofuran, And so on.
보다 구체적으로, 본 발명의 화학식 1로 표시되는 화합물은 두 개 이상의 벤조트리아졸, 인다졸 등과 같은 5원 방향족 헤테로 고리를 포함하는 치환기가 결합된 모이어티에 전자끌개그룹(EWG)이 직접 또는 링커기를 통해 연결된 구조이거나, 또는 벤조트리아졸, 인다졸 등과 같은 5원 방향족 헤테로 고리를 포함하는 치환기와 인덴, 벤조퓨란 등과 같은 5원 방향족 고리를 포함하는 치환기가 결합된 모이어티에 전자끌개그룹(EWG)이 직접 또는 링커기를 통해 연결된 구조를 가진다.More specifically, the compound represented by the formula (1) of the present invention is a compound in which an electron-withdrawing group (EWG) is bonded directly or in a linker group to a moiety having a substituent bonded thereto including a 5-membered aromatic heterocycle such as benzotriazole, Or an electron withdrawing group (EWG) is attached to a moiety having a substituent containing a 5-membered aromatic heterocycle such as benzotriazole, indazole, etc. and a 5-membered aromatic ring such as indene, benzofuran or the like, And has a structure directly or through a linker group.
발광층 내에 도판트로 사용한 Ir(ppy)의 T1값(2.4eV)보다 전자수송층으로 사용한 Alq의 T1값(2.0eV)이 현저히 낮은데 반해 본 발명의 화합물들의 경우, Ir(ppy) 보다 대체적으로 높은 T1 값(2.4eV이상)을 나타내어 정공 저지 능력(hole blocking ability)이 향상될 뿐만 아니라, 발광층 내에서 여기자(exciton)가 잘 머무를 수 있는 확률을 상대적으로 높이기 때문인 것으로 판단된다.The T1 value (2.0 eV) of Alq used as the electron transport layer was significantly lower than the T1 value (2.4 eV) of Ir (ppy) used as a dopant in the light emitting layer, whereas the T1 value (2.0 eV) (2.4 eV or more), which improves the hole blocking ability and increases the probability that the exciton can stay well in the light emitting layer.
또한, 상기 5원 방향족 고리 또는 5원 방향족헤테로 고리는 분자량이 기존 화합물 보다 적기 때문에, 증착 시 재료들 보다 상대적으로 낮은 온도에서 증착이 가능하므로 공정성이 좋고 열안정성이 향상된다.In addition, since the 5-membered aromatic ring or the 5-membered aromatic heterocycle has a lower molecular weight than that of the conventional compound, the deposition is possible at a relatively lower temperature than the materials at the time of deposition, so that the processability is improved and the thermal stability is improved.
따라서, 본 발명의 화학식 1로 표시되는 화합물은 유기 전계 발광 소자의 유기물층 재료, 바람직하게는 전자 수송층/주입층 재료로 사용될 수 있다.Therefore, the compound represented by the formula (1) of the present invention can be used as an organic material layer of an organic electroluminescent device, preferably an electron transporting layer / injection layer material.
또한, 상기 화학식 1의 화합물을 포함하는 유기 전계 발광 소자는 성능 및 수명 특성이 크게 향상될 수 있고, 이러한 유기 전계 발광 소자가 적용된 풀 칼라 유기 발광 패널도 성능이 극대화될 수 있다.In addition, the organic electroluminescent device including the compound of Formula 1 can be greatly improved in performance and lifetime, and the full-color organic luminescent panel to which such an organic electroluminescent device is applied can also maximize its performance.
본 발명의 일례에 따른 유기 화합물은 하기 화학식 1로 표시된다.An organic compound according to an example of the present invention is represented by the following formula (1).
[화학식 1][Chemical Formula 1]
상기 화학식 1에서,In Formula 1,
X1 내지 X6 은 각각 서로 동일하거나 상이하며, C, N 중 하나의 원자를 함유하고,X 1 to X 6 are the same or different from each other and contain one atom of C and N,
A와 B는 각각 서로 동일하거나 상이하며, 독립적으로 하기 화학식 2 또는 화학식 3으로 표시될 수 있고A and B are the same or different from each other and independently can be represented by the following formula (2) or (3)
[화학식 2](2)
[화학식 3](3)
상기 화학식 2 또는 화학식 3에서,In Formula 2 or Formula 3,
X7 내지 X9 은 각각 서로 동일하거나 상이하며, S, O, N(Ar1), C(Ar2)(Ar3) 중 어느 하나의 원자를 함유하고,X 7 to X 9 are the same or different from each other and contain any one of S, O, N (Ar 1 ) and C (Ar 2 ) (Ar 3 )
n은 0 내지 4의 정수이며,n is an integer of 0 to 4,
C는 하기 화학식 4 로 표현되는 치환기이고,C is a substituent represented by the following formula (4)
[화학식 4][Chemical Formula 4]
상기 화학식 4에서,In Formula 4,
*은 X1 내지 X6 와 결합이 이루어지는 부분을 의미하고;* Represents a moiety in which X 1 to X 6 are bonded;
L1은 단일결합, C6~C18의 아릴렌기 및 핵원자수 5 내지 18개의 헤테로아릴렌기로 이루어진 군에서 선택되며;L 1 is selected from the group consisting of a single bond, a C 6 to C 18 arylene group and a heteroarylene group having 5 to 18 nuclear atoms;
R1 내지 R3와 Ar1 내지 Ar3은 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성하며; R 1 to R 3 and Ar 1 to Ar 3 are each independently selected from hydrogen, deuterium, halogen, cyano, nitro, C 1 to C 40 alkyl, C 2 to C 40 alkenyl, C 2 to C 40 alkynyl, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 6 ~ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 1 ~ alkyloxy group of C 40, A C 6 to C 60 aryloxy group, a C 3 to C 40 alkylsilyl group, a C 6 to C 60 arylsilyl group, a C 1 to C 40 alkylboron group, a C 6 to C 60 arylboron group, C 6 ~ C 60 aryl phosphazene group, C 6 ~ C 60 mono or diaryl phosphine blood group and a C 6 ~, or selected from the group consisting of an aryl amine of the C 60, the combined group adjacent to form a condensed ring ;
상기 L1의 아릴렌기 및 헤테로아릴렌기와, 상기 R1 및 R2 와 Ar1 내지 Ar3 의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다.An alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group or a heterocyclic group of the above-mentioned L 1 and an arylene group and a heteroarylene group of R 1 and R 2 and Ar 1 to Ar 3 , A heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkylboron group, an arylboron group, an arylphosphonyl group, a mono- or diarylphosphinyl group, and an arylsilyl group are each independently selected from deuterium, halogen, cyano, nitro, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, an alkynyl group of C 2 ~ C 40, C 6 ~ aryl group of C 60, nuclear atoms of 5 to 60 heteroaryl group, C 6 ~ C aryloxy 60, C 1 ~ C 40 alkyloxy group of, C 6 ~ C 60 aryl amine group, C 3 ~ cycloalkyl group of C 40, nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkylsilyl group, C 1 ~ C 40 alkyl group of boron, C 6 ~ C 60 aryl group of boron, C 6 ~ C 60 aryl phosphazene group, C 6 ~ C 60 of the mono or diaryl phosphine If group and a C 6 ~ C substituted with one or more substituents selected from the 60 group consisting of aryl silyl or is unsubstituted, substituted by a plurality of substituents, they may be the same or different from each other.
본 발명의 일례에 따르면, 상기 화학식 1로 표시되는 화합물은 하기 화학식 5로 표시될 수 있다.According to an embodiment of the present invention, the compound represented by Formula 1 may be represented by Formula 5 below.
상기 화학식 5에서,In Formula 5,
X7 내지 X9, n, R1 내지 R3 및 L1 각각은 상기 화학식 1 내지 상기 화학식 3에서 정의된 바와 같다.X 7 to X 9 , n, R 1 To R 3 and L 1 each are as defined in Formula 1 to Formula 3.
본 발명의 바람직한 일례에 따르면, 상기 화학식 1의 A는 하기 구조에서 선택될 수 있으나, 이에 한정되는 것은 아니다.According to a preferred embodiment of the present invention, A in Formula 1 may be selected from the following structures, but is not limited thereto.
, , , , , , , ,
, , , , , ,
, , . , , .
본 발명의 바람직한 일례에 따르면, 상기 화학식 1의 B는 하기 구조에서 선택될 수 있으나, 이에 한정되는 것은 아니다.According to a preferred embodiment of the present invention, B in Formula 1 may be selected from the following structures, but is not limited thereto.
, , , , , , , ,
, , , , , ,
, , , , , , , ,
, , , , , ,
, , , , , ,
, , , , , ,
. .
본 발명의 바람직한 일례에 따르면, 상기 L1은 피리미딘 또는 트리아진일 수 있다. 또한, 상기 R2와 R3는 서로 동일하거나 상이하며, 하기 구조에서 선택될 수 있으나 이에 한정되는 것은 아니다.According to a preferred embodiment of the present invention, L < 1 > may be pyrimidine or triazine. R 2 and R 3 may be the same or different and may be selected from the following structures, but are not limited thereto.
, , , . , , , .
본 발명의 바람직한 일례에 따르면, 상기 화학식 1의 C는 하기 구조에서 선택될 수 있으나, 이에 한정되는 것은 아니다.According to a preferred embodiment of the present invention, C in Formula 1 may be selected from the following structures, but is not limited thereto.
, , , ,
, . , .
본 발명의 일례에 따른 화학식 1로 표시되는 화합물의 예로는 화합물 R1 내지 R120 등이 있는데, 이에 한정되는 것은 아니다.Examples of the compound represented by formula (1) according to an example of the present invention include, but are not limited to, compounds R1 to R120.
본 발명에서 "알킬"은 탄소수 1 내지 40의 직쇄 또는 측쇄의 포화 탄화수소로부터 수소 원자를 제거하여 얻어지는 1가의 작용기를 의미하며, 이의 비제한적인 예로는 메틸, 에틸, 프로필, 이소부틸, sec-부틸, 펜틸, iso-아밀, 헥실 등이 있다.In the present invention, "alkyl" means a monovalent functional group obtained by removing a hydrogen atom 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, hexyl, and the like.
본 발명에서 "시클로알킬"은 탄소수 3 내지 40의 모노사이클릭 또는 폴리사이클릭 비-방향족 탄화수소(포화 고리형 탄화수소)로부터 수소 원자를 제거하여 얻어지는 1가의 작용기를 의미한다. 이의 비제한적인 예로는 시클로프로필, 시클로펜틸, 시클로헥실, 노르보닐(norbornyl), 아다만틴(adamantine)등이 있다."Cycloalkyl" in the present invention means a monovalent functional group obtained by removing a hydrogen atom from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms (saturated cyclic hydrocarbon). Non-limiting examples thereof include cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
본 발명에서 "헤테로시클로알킬"은 핵원자수 3 내지 40의 비-방향족 탄화수소(포화 고리형 탄화수소)로부터 수소 원자를 제거하여 얻어지는 1가의 작용기를 의미하며, 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3의 탄소가 N, O 또는 S와 같은 헤테로 원자로 치환된다. 이의 비제한적인 예로는 모르폴린, 피페라진 등이 있다.In the present invention, "heterocycloalkyl" means a monovalent functional group obtained by removing a hydrogen atom from a non-aromatic hydrocarbon (saturated cyclic hydrocarbon) having 3 to 40 nuclear atoms, and includes at least one carbon atom in the ring, preferably 1 Lt; RTI ID = 0.0 > N, < / RTI > O or S. Non-limiting examples thereof include morpholine, piperazine, and the like.
본 발명에서 "아릴"은 단독 고리 또는 2 이상의 고리가 조합된, 탄소수 6 내지 60의 방향족 탄화수소로부터 수소 원자를 제거하여 얻어지는 1가의 작용기를 의미한다. 이때, 2 이상의 고리는 서로 단순 부착되거나 축합된 형태로 부착될 수 있다. 이의 비제한적인 예로는 페닐, 비페닐, 터페닐(terphenyl), 나프틸, 페난트릴, 안트릴 등이 있다.&Quot; Aryl " in the present invention means a monovalent functional group obtained by removing a hydrogen atom from an aromatic hydrocarbon having 6 to 60 carbon atoms in which a single ring or two or more rings are combined. At this time, the two or more rings may be attached to each other in a simple attached or condensed form. Non-limiting examples thereof include phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthryl, and the like.
본 발명에서 "헤테로아릴"은 핵원자수 5 내지 60의 모노헤테로사이클릭 또는 폴리헤테로사이클릭 방향족 탄화수소로부터 수소 원자를 제거하여 얻어지는 1가의 작용기로서, 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3의 탄소가 질소(N), 산소(O), 황(S) 또는 셀레늄(Se)과 같은 헤테로원자로 치환된다. 이때, 헤테로아릴은 2 이상의 고리가 서로 단순 부착되거나 축합된 형태로 부착될 수 있고, 나아가 아릴기와의 축합된 형태도 포함할 수 있다. 이러한 헤테로아릴의 비제한적인 예로는 피리딜, 피라지닐, 피리미디닐, 피리다지닐, 트리아지닐과 같은 6원 모노사이클릭 고리, 페녹사티에닐(phenoxathienyl), 인돌리지닐(indolizinyl), 인돌릴(indolyl), 퓨리닐(purinyl), 퀴놀릴(quinolyl), 벤조티아졸(benzothiazole), 카바졸릴(carbazolyl)과 같은 폴리사이클릭 고리 및 2-퓨라닐, N-이미다졸릴, 2-이속사졸릴, 2-피리디닐, 2-피리미디닐 등을 들 수 있다.In the present invention, "heteroaryl" is a monovalent functional group obtained by removing a hydrogen atom from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms, and is a monovalent group having at least one carbon atom, preferably 1 to 3 carbon atoms in the ring Is replaced with a heteroatom such as nitrogen (N), oxygen (O), sulfur (S) or selenium (Se). At this time, the heteroaryl may be attached in a form in which two or more rings are attached or condensed to each other, and may further include a condensed form with an aryl group. Non-limiting examples of such heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, indole A polycyclic ring such as indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, and a heterocyclic ring such as 2-furanyl, N-imidazolyl, 2- 2-pyridinyl, 2-pyrimidinyl, and the like.
본 발명에서 "알킬옥시"는 RO-로 표시되는 1가의 작용기를 의미하며, 상기 R은 탄소수 1 내지 40의 알킬로서, 직쇄(linear), 측쇄(branched) 또는 사이클릭(cyclic) 구조를 포함할 수 있다. 이러한 알킬옥시의 비제한적인 예로는 메톡시, 에톡시, n-프로폭시, 1-프로폭시, t-부톡시, n-부톡시, 펜톡시 등을 들 수 있다.In the present invention, " alkyloxy " means a monovalent functional group represented by RO-, wherein R is an alkyl having 1 to 40 carbon atoms and includes a linear, branched or cyclic structure . Non-limiting examples of such alkyloxy include methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.
본 발명에서 "아릴옥시"는 R'O-로 표시되는 1가의 작용기를 의미하며, 상기 R'는 탄소수 6 내지 60의 아릴이다. 이러한 아릴옥시의 비제한적인 예로는 페닐옥시, 나프틸옥시, 디페닐옥시 등이 있다.In the present invention, "aryloxy" means a monovalent functional group represented by R'O-, and R 'is aryl having 6 to 60 carbon atoms. Non-limiting examples of such aryloxy include phenyloxy, naphthyloxy, diphenyloxy, and the like.
본 발명에서 "알킬실릴"은 탄소수 1 내지 40의 알킬로 치환된 실릴을 의미하며, "아릴실릴"은 탄소수 6 내지 60의 아릴로 치환된 실릴을 의미하고, "알킬보론기"는 탄소수 1 내지 40의 알킬로 치환된 보론기를 의미하며, "아릴보론기"는 탄소수 6 내지 60의 아릴로 치환된 보론기를 의미하며, "아릴포스핀기"는 탄소수 1 내지 60의 아릴로 치환된 포스핀기를 의미하며, "아릴아민"은 탄소수 6 내지 60의 아릴로 치환된 아민을 의미한다.&Quot; Alkylsilyl " means silyl substituted with alkyl having 1 to 40 carbon atoms, " arylsilyl " means silyl substituted with aryl having 6 to 60 carbon atoms, Quot; means a boron group substituted with aryl having 6 to 60 carbon atoms, " arylphosphine group " means a phosphine group substituted with aryl having 1 to 60 carbon atoms, &Quot; arylamine " means an amine substituted with aryl having 6 to 60 carbon atoms.
본 발명에서 사용되는 "축합 고리"는 축합 지방족 고리, 축합 방향족 고리, 축합 헤테로지방족 고리, 축합 헤테로방향족 고리 또는 이들의 조합된 형태를 의미한다.As used herein, " fused ring " means a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring, a fused heteroaromatic ring, or a combination thereof.
2. 유기 전계 발광 소자2. Organic electroluminescent device
한편, 본 발명은 전술한 화학식 1로 표시되는 화합물을 포함하는 유기 전계 발광 소자를 제공한다.The present invention also provides an organic electroluminescent device comprising the compound represented by the above-mentioned formula (1).
구체적으로, 본 발명의 일례는 양극(anode), 음극(cathode) 및 상기 양극과 음극 사이에 개재된 1층 이상의 유기물층을 포함하며, 상기 1층 이상의 유기물층 중 적어도 하나는 상기 화학식 1로 표시되는 화합물을 포함하는 유기 전계 발광 소자를 제공한다. 이때, 상기 화학식 1로 표시되는 화합물은 단독으로 사용되거나, 또는 2 이상이 혼합되어 사용될 수 있다.More specifically, one example of the present invention includes an anode, a 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 And an organic electroluminescent device. At this time, the compound represented by the formula (1) may be used alone or in combination of two or more.
본 발명의 일례에 따르면, 상기 1층 이상의 유기물층은 정공 주입층, 정공 수송층, 발광층, 전자 수송층 및 전자 주입층을 포함하는데, 이 중에서 적어도 하나의 유기물층이 상기 화학식 1로 표시되는 화합물을 포함할 수 있다. 바람직하게는 상기 화학식 1의 화합물을 포함하는 유기물층은 전자 수송층일 수 있다. 본 발명의 일례에 따른 유기 전계 발광 소자는 유기물층 중 적어도 하나 이상(예컨대, 발광층, 전자 수송층, 발광 보조층 중 하나 이상)이 상기 화학식 1로 표시되는 화합물을 포함하도록 형성하는 것을 제외하고는, 당 기술 분야에 알려져 있는 재료 및 방법을 이용하여 다른 유기물층 및 전극을 형성하여 제조될 수 있다.According to an embodiment of the present invention, the at least one organic material layer may include a hole injection layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injection layer. have. Preferably, the organic material layer containing the compound of Formula 1 may be an electron transporting layer. An organic electroluminescent device according to an example of the present invention is a device in which at least one or more of an organic material layer (for example, at least one of a light emitting layer, an electron transporting layer, and a light emitting auxiliary layer) May be produced by forming other organic layers and electrodes using materials and methods known in the art.
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 한정되지 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 발명에서 사용 가능한 기판으로는 특별히 한정되지 않으며, 실리콘 웨이퍼, 석영, 유리판, 금속판, 플라스틱 필름 및 시트 등이 사용될 수 있다.The substrate usable in the present invention is not particularly limited, and a silicon wafer, quartz, a glass plate, a metal plate, a plastic film and a sheet can be used.
또 양극 물질로는 i)바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금, ii)아연산화물, 인듐산화물, 인듐 주석 산화물(ITO), 인듐 아연 산화물(IZO)과 같은 금속 산화물, iii)ZnO:Al 또는 SnO2:Sb와 같은 금속과 산화물의 조합, iv)폴리티오펜, 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜](PEDT), 폴리피롤 또는 폴리아닐린과 같은 전도성 고분자 및 v)카본블랙 등이 사용될 수 있으나, 이에 한정되지는 않는다.Examples of the positive electrode material include metal oxides such as i) metals such as vanadium, chromium, copper, zinc and gold or their alloys, ii) zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO) iii) ZnO: SnO 2 or Al: a combination of a metal and an oxide such as Sb, iv), polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) T (PEDT), a conductive polymer such as polypyrrole or polyaniline, and v) carbon black may be used, but the present invention is not limited thereto.
또한 음극 물질로는 마그네슘, 칼슘, 나트륨, 칼륨, 타이타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석, 또는 남과 같은 금속 또는 이들의 합금 및 LiF/Al 또는 LiO2/Al과 같은 다층 구조 물질 등이 사용될 수 있으나, 이에 한정되지는 않는다.Examples of the negative electrode material include a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin or others or an alloy thereof and a multilayer structure such as LiF / Al or LiO 2 / Materials, and the like may be used, but are not limited thereto.
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.
[[ 준비예Preparation Example 1] A1의 합성 1] Synthesis of A1
질소 기류 하에서 4-(biphenyl-4-yl)-6-(3,5-dibromophenyl)-2-phenylpyrimidine 9.2 g(16.9 mmol), 1H-indazole 2.4 g(20.2 mmol), 0.8 g(5 mol%)의 Pd2(dba)3, tri-tert-butylphosphine 0.2 g(0.8 mmol) 및 Sodium tert-butoxide 5.0 g(50.6 mmol)와 100 ml의 Toluene을 넣고 110℃에서 4시간 동안 교반하였다.9.2 g (16.9 mmol) of 4- (biphenyl-4-yl) -6- (3,5-dibromophenyl) -2-phenylpyrimidine, 2.4 g (20.2 mmol) of 1H- 0.2 g (0.8 mmol) of Pd 2 (dba) 3 , tri- tert- butylphosphine and 5.0 g (50.6 mmol) of sodium tert-butoxide and 100 ml of toluene were placed and stirred at 110 ° C for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 A1 6.4 g(11.0 mmol, 수율 65%)을 얻었다.After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO 4 . The residue was purified by column chromatography to obtain 6.4 g (11.0 mmol, yield 65%) of the target compound A1.
GC-Mass (이론치: 579.49 g/mol, 측정치: 579 g/mol)GC-Mass (calculated: 579.49 g / mol, measured: 579 g / mol)
1H-NMR: δ 7.41-7.55(m, 11H), 7.65-7.88(m, 4H), 8.01-8.28(m, 8H)1 H-NMR:? 7.41-7.55 (m, 11H), 7.65-7.88 (m, 4H), 8.01-8.28
[[ 준비예Preparation Example 2] A2의 합성 2] Synthesis of A2
질소 기류 하에서 4-(biphenyl-4-yl)-6-(3,5-dibromophenyl)-2-phenylpyrimidine 9.2 g(16.9 mmol), 3H-benzo[e]indazole 3.4 g(20.2 mmol), 0.8 g(5 mol%)의 Pd2(dba)3, tri-tert-butylphosphine 0.2 g(0.8 mmol) 및 Sodium tert-butoxide 5.0 g(50.6 mmol)와 100 ml의 Toluene을 넣고 110℃에서 4시간 동안 교반하였다.A mixture of 9.2 g (16.9 mmol) of 4- (biphenyl-4-yl) -6- (3,5-dibromophenyl) -2-phenylpyrimidine and 3.4 g (20.2 mmol) of 3H- Pd 2 (dba) of 5 mol%) 3, into a tri- tert -butylphosphine 0.2 g (0.8 mmol ) and Sodium tert-butoxide 5.0 g (50.6 mmol) and 100 ml of Toluene was stirred at 110 ℃ for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 A2 6.9 g(11.0 mmol, 수율 65%)을 얻었다.After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO 4 . The residue was purified by column chromatography to obtain 6.9 g (11.0 mmol, yield 65%) of A2 as a target compound.
GC-Mass (이론치: 629.55 g/mol, 측정치: 629 g/mol)GC-Mass (calculated: 629.55 g / mol, measured: 629 g / mol)
1H-NMR: δ 7.41-7.55(m, 11H), 7.65-7.88(m, 4H), 8.01-8.31(m, 10H)1 H-NMR:? 7.41-7.55 (m, 11H), 7.65-7.88 (m, 4H), 8.01-8.31 (m,
[[ 준비예Preparation Example 3] A3의 합성 3] Synthesis of A3
질소 기류 하에서 4-(biphenyl-4-yl)-6-(3,5-dibromophenyl)-2-(pyridin-4-yl)pyrimidine 9.2 g(16.9 mmol), 3-(pyridin-4-yl)-1H-indazole 4.0 g(20.2 mmol), 0.8 g(5 mol%)의 Pd2(dba)3, tri-tert-butylphosphine 0.2 g(0.8 mmol) 및 Sodium tert-butoxide 5.0 g(50.6 mmol)와 100 ml의 Toluene을 넣고 110℃에서 4시간 동안 교반하였다.9.2 g (16.9 mmol) of 3- (pyridin-4-yl) -6- (3,5-dibromophenyl) -2- 1H-indazole 4.0 g (20.2 mmol ), 0.8 g (5 mol%) of Pd 2 (dba) 3, tri- tert -butylphosphine 0.2 g (0.8 mmol) and Sodium tert-butoxide 5.0 g (50.6 mmol) and 100 ml Of toluene was added thereto, followed by stirring at 110 DEG C for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 A3, 7.2 g(11.0 mmol, 수율 65%)을 얻었다.After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO 4 . The residue was purified by column chromatography to obtain 7.2 g (11.0 mmol, yield 65%) of target compound A3.
GC-Mass (이론치: 657.56 g/mol, 측정치: 657 g/mol)GC-Mass (calculated: 657.56 g / mol, measured: 657 g / mol)
1H-NMR: δ 7.42-7.53(m, 8H), 7.69-7.94(m, 6H), 8.01-8.25(m, 6H), 8.45~8.75(m, 5H).1 H-NMR:? 7.42-7.53 (m, 8H), 7.69-7.94 (m, 6H), 8.01-8.25 (m, 6H), 8.45-8.
[[ 준비예Preparation Example 4] A4의 합성 4] Synthesis of A4
질소 기류 하에서 4-(2-(3,5-dibromophenyl)-4,6-diphenyl-1,3,5-triazine 7.9(16.9 mmol), 1H-indazole 2.4 g(20.2 mmol), 0.8 g(5 mol%)의 Pd2(dba)3, tri-tert-butylphosphine 0.2 g(0.8 mmol) 및 Sodium tert-butoxide 5.0 g(50.6 mmol)와 100 ml의 Toluene을 넣고 110℃에서 4시간 동안 교반하였다.2.4 g (20.2 mmol) of 4- (2- (3,5-dibromophenyl) -4,6-diphenyl-1,3,5-triazine 7.9 %) was added to the Pd 2 (dba) 3, tri- tert -butylphosphine 0.2 g (0.8 mmol) and Sodium tert-butoxide 5.0 g (50.6 mmol) and 100 ml of Toluene was stirred at 110 ℃ for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 A4 5.5 g(11.0 mmol, 수율 65%)을 얻었다.After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO 4 . The residue was purified by column chromatography to obtain 5.5 g of the target compound A4 (11.0 mmol, yield 65%).
GC-Mass (이론치: 504.38 g/mol, 측정치: 504 g/mol)GC-Mass (calculated: 504.38 g / mol, measured: 504 g / mol)
1H-NMR: δ 7.41-7.56(m, 8H), 7.65-7.75(m, 2H), 8.01-8.31(m, 8H)1 H-NMR:? 7.41-7.56 (m, 8H), 7.65-7.75 (m, 2H), 8.01-8.31
[[ 준비예Preparation Example 5] A5의 합성 5] Synthesis of A5
질소 기류 하에서 2,4-bis(dibenzo[b,d]furan-2-yl)-6-(3,5-dibromophenyl)-1,3,5-triazine 10.9 g(16.9 mmol), 1H-indazole 2.4 g(20.2 mmol), 0.8 g(5 mol%)의 Pd2(dba)3, tri-tert-butylphosphine 0.2 g(0.8 mmol) 및 Sodium tert-butoxide 5.0 g(50.6 mmol)와 100 ml의 Toluene을 넣고 110℃에서 4시간 동안 교반하였다.10.9 g (16.9 mmol) of 2,4-bis (dibenzo [b, d] furan-2-yl) -6- (3,5-dibromophenyl) -1,3,5- g (20.2 mmol), 0.8 g (5 mol%) into the Pd 2 (dba) 3, tri- tert -butylphosphine 0.2 g (0.8 mmol) and Sodium tert-butoxide 5.0 g (50.6 mmol) and 100 ml of Toluene Followed by stirring at 110 ° C for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 A5, 7.5 g(11.0 mmol, 수율 65%)을 얻었다.After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO 4 . The residue was purified by column chromatography to obtain 7.5 g (11.0 mmol, yield 65%) of the target compound A5.
GC-Mass (이론치: 684.54 g/mol, 측정치: 684 g/mol)GC-Mass (calculated: 684.54 g / mol, measured: 684 g / mol)
1H-NMR: δ 7.32-7.43(m, 7H), 7.51-7.74(m, 8H), 7.80-7.93(m, 4H), 8.01-8.25(m, 3H)8H), 7.80-7.93 (m, 4H), 8.01-8.25 (m, 3H), 7.51-7.74 (m,
[[ 준비예Preparation Example 6] A6의 합성 6] Synthesis of A6
질소 기류 하에서 4-(biphenyl-4-yl)-6-(3,5-dibromophenyl)-2-phenylpyrimidine 9.2 g(16.9 mmol), 1-phenyl-1H-indazol-5-ylboronic acid 4.8 g(20.2 mmol), 1.0 g(5 mol%)의 Pd(PPh3)4 및 potassium carbonate 7.0 g(50.6 mmol)와 80 ml/40 ml/40 ml의 Toluene/H2O/Ethanol를 넣고 110℃에서 3시간 동안 교반하였다.9.2 g (16.9 mmol) of 4- (biphenyl-4-yl) -6- (3,5-dibromophenyl) -2-phenylpyrimidine and 4.8 g ), 1.0 g (5 mol%) of Pd (PPh 3 ) 4 and 7.0 g (50.6 mmol) of potassium carbonate and 80 ml / 40 ml / 40 ml of toluene / H 2 O / Lt; / RTI >
반응 종료 후, 메틸렌클로라이드를 이용하여 유기층을 분리하고 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 A6(7.2 g, 11.0 mmol, 수율 65%)을 얻었다.After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO 4 . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the target compound A6 (7.2 g, 11.0 mmol, yield 65%).
GC-Mass (이론치: 655.58 g/mol, 측정치: 655 g/mol)GC-Mass (calculated: 655.58 g / mol, measured: 655 g / mol)
1H-NMR: δ 7.42-7.54(m, 13H), 7.61-7.84(m, 6H), 8.09-8.28(m, 8H)1 H-NMR:? 7.42-7.54 (m, 13H), 7.61-7.84 (m, 6H), 8.09-8.28
[[ 준비예Preparation Example 7] A7의 합성 7] Synthesis of A7
질소 기류 하에서 4-(biphenyl-4-yl)-6-(3,5-dibromophenyl)-2-phenylpyrimidine 9.2 g(16.9 mmol), 1H-benzo[d][1,2,3]triazole 2.4 g(20.2 mmol), 0.8 g(5 mol%)의 Pd2(dba)3, tri-tert-butylphosphine 0.2 g(0.8 mmol) 및 Sodium tert-butoxide 5.0 g(50.6 mmol)와 100 ml의 Toluene을 넣고 110℃에서 4시간 동안 교반하였다.A solution of 9.2 g (16.9 mmol) of 4- (biphenyl-4-yl) -6- (3,5-dibromophenyl) -2-phenylpyrimidine and 2.4 g 0.2 g (0.8 mmol) of Pd 2 (dba) 3 , tri- tert- butylphosphine and 5.0 g (50.6 mmol) of sodium tert-butoxide and 100 ml of toluene, Lt; / RTI > for 4 h.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 A7 6.6 g(11.3 mmol, 수율 67%)을 얻었다.After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO 4 . The residue was purified by column chromatography to obtain 6.6 g (11.3 mmol, yield 67%) of the desired compound A7.
GC-Mass (이론치: 580.48 g/mol, 측정치: 580 g/mol)GC-Mass (calculated: 580.48 g / mol, measured: 580 g / mol)
1H-NMR: δ 7.41-7.54(m, 11H), 7.63-7.88(m, 4H), 8.01-8.27(m, 7H)1 H-NMR:? 7.41-7.54 (m, 11H), 7.63-7.88 (m, 4H), 8.01-8.27 (m, 7H)
[[ 준비예Preparation Example 8] A8의 합성 8] Synthesis of A8
질소 기류 하에서 4-(biphenyl-4-yl)-6-(3,5-dibromophenyl)-2-phenylpyrimidine 9.2 g(16.9 mmol), 3H-naphtho[2,1-d][1,2,3]triazole 3.4 g(20.2 mmol), 0.8 g(5 mol%)의 Pd2(dba)3, tri-tert-butylphosphine 0.2 g(0.8 mmol) 및 Sodium tert-butoxide 5.0 g(50.6 mmol)와 100 ml의 Toluene을 넣고 110℃에서 4시간 동안 교반하였다.3-naphtho [2,1-d] [1,2,3] triazol-4-yl) -6- (3,5-dibromophenyl) triazole 3.4 g (20.2 mmol), 0.8 g (5 mol%) of Pd 2 (dba) 3, tri- tert -butylphosphine 0.2 g (0.8 mmol) tert-butoxide and 5.0 g of Sodium (50.6 mmol) and 100 ml Toluene And the mixture was stirred at 110 ° C for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 A8 7.1 g(11.3 mmol, 수율 67%)을 얻었다.After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO 4 . The residue was purified by column chromatography to obtain 7.1 g (11.3 mmol, yield 67%) of the desired compound A8.
GC-Mass (이론치: 630.53 g/mol, 측정치: 630 g/mol)GC-Mass (calculated: 630.53 g / mol, measured: 630 g / mol)
1H-NMR: δ 7.42-7.55(m, 11H), 7.65-7.88(m, 4H), 8.01-8.31(m, 9H)1 H-NMR:? 7.42-7.55 (m, 11H), 7.65-7.88 (m, 4H), 8.01-8.31 (m, 9H)
[[ 준비예Preparation Example 9] A9의 합성 9] Synthesis of A9
질소 기류 하에서 4-(biphenyl-4-yl)-6-(3,5-dibromophenyl)-2-(pyridin-4-yl)pyrimidine 9.2 g(16.9 mmol), 1H-benzo[d][1,2,3]triazole 4.0 g(20.2 mmol), 0.8 g(5 mol%)의 Pd2(dba)3, tri-tert-butylphosphine 0.2 g(0.8 mmol) 및 Sodium tert-butoxide 5.0 g(50.6 mmol)와 100 ml의 Toluene을 넣고 110℃에서 4시간 동안 교반하였다.9.2 g (16.9 mmol) of 1H-benzo [d] [1,2] pyrimidine were added to a solution of 4- (biphenyl-4-yl) -6- , 3] triazole 4.0 g (20.2 mmol), 0.8 g (5 mol%) of Pd 2 (dba) 3, tri- tert -butylphosphine 0.2 g (0.8 mmol) and Sodium tert-butoxide 5.0 g (50.6 mmol) and 100 ml of toluene was added thereto, followed by stirring at 110 ° C for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 A9 6.6 g(11.3 mmol, 수율 67%)을 얻었다.After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO 4 . The residue was purified by column chromatography to obtain 6.6 g (11.3 mmol, yield 67%) of the desired compound A9.
GC-Mass (이론치: 581.46 g/mol, 측정치: 581 g/mol)GC-Mass (calculated: 581.46 g / mol, measured: 581 g / mol)
1H-NMR: δ 7.41-7.52(m, 8H), 7.69-7.94(m, 6H), 8.01-8.25(m, 6H), 8.43-8.73(m, 4H),1 H-NMR:? 7.41-7.52 (m, 8H), 7.69-7.94 (m, 6H), 8.01-8.25 (m, 6H), 8.43-8.73
[[ 준비예Preparation Example 10] A10의 합성 10] Synthesis of A10
질소 기류 하에서 4-(2-(3,5-dibromophenyl)-4,6-diphenyl-1,3,5-triazine 7.9 g(16.9 mmol), 1H-benzo[d][1,2,3]triazole 2.4 g(20.2 mmol), 0.8 g(5 mol%)의 Pd2(dba)3, tri-tert-butylphosphine 0.2 g(0.8 mmol) 및 Sodium tert-butoxide 5.0 g(50.6 mmol)와 100 ml의 Toluene을 넣고 110℃에서 4시간 동안 교반하였다.A solution of 7.9 g (16.9 mmol) of 4- (2- (3,5-dibromophenyl) -4,6-diphenyl-1,3,5-triazine and 1 H-benzo [d] [1,2,3] triazole a 2.4 g (20.2 mmol), 0.8 g (5 mol%) of Pd 2 (dba) 3, tri- tert -butylphosphine 0.2 g (0.8 mmol) and Sodium tert-butoxide 5.0 g (50.6 mmol) and 100 ml of Toluene And the mixture was stirred at 110 ° C for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 A10 5.7 g(11.3 mmol, 수율 67%)을 얻었다.After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO 4 . The residue was purified by column chromatography to obtain 5.7 g (11.3 mmol, yield 67%) of the desired compound A10.
GC-Mass (이론치: 505.37 g/mol, 측정치: 505 g/mol)GC-Mass (calculated: 505.37 g / mol, measured: 505 g / mol)
1H-NMR: δ 7.41-7.56(m, 8H), 7.65-7.75(m, 2H), 8.01-8.31 (m, 7H)1 H-NMR:? 7.41-7.56 (m, 8H), 7.65-7.75 (m, 2H), 8.01-8.31 (m,
[[ 준비예Preparation Example 11] A11의 합성 11] Synthesis of A11
질소 기류 하에서 2,4-bis(dibenzo[b,d]furan-2-yl)-6-(3,5-dibromophenyl)-1,3,5-triazine 10.9 g(16.9 mmol), 1H-benzo[d][1,2,3]triazole 2.4 g(20.2 mmol), 0.8 g(5 mol%)의 Pd2(dba)3, tri-tert-butylphosphine 0.2 g(0.8 mmol) 및 Sodium tert-butoxide 5.0 g(50.6 mmol)와 100 ml의 Toluene을 넣고 110℃에서 4시간 동안 교반하였다.A solution of 10.9 g (16.9 mmol) of 2,4-bis (dibenzo [b, d] furan-2-yl) -6- (3,5- dibromophenyl) -1,3,5- d] [1,2,3] triazole, 0.2 g (0.8 mmol) of Pd 2 (dba) 3 , tri- tert- butylphosphine and 0.8 g (5 mol%) of sodium tert- (50.6 mmol) and 100 ml of toluene, and the mixture was stirred at 110 ° C for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 A11 7.7 g(11.3 mmol, 수율 67%)을 얻었다.After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO 4 . The residue was purified by column chromatography to obtain 7.7 g (11.3 mmol, yield 67%) of the desired compound A11.
GC-Mass (이론치: 685.53 g/mol, 측정치: 685 g/mol)GC-Mass (calculated: 685.53 g / mol, measured: 685 g / mol)
1H-NMR: δ 7.32-7.43(m, 7H), 7.51-7.73(m, 8H), 7.80-7.92(m, 4H), 8.00-8.23(m, 2H)8H), 7.80-7.92 (m, 4H), 8.00-8.23 (m, 2H), 7.50-7.73 (m,
[[ 준비예Preparation Example 12] A12의 합성 12] Synthesis of A12
질소 기류 하에서 4-(biphenyl-4-yl)-6-(3,5-dibromophenyl)-2-phenylpyrimidine 9.2 g(16.9 mmol), 1-phenyl-1H-benzo[d][1,2,3]triazol-5-ylboronic acid 4.8 g(20.2 mmol), 1.0 g(5 mol%)의 Pd(PPh3)4 및 potassium carbonate 7.0 g(50.6 mmol)와 80 ml/40 ml/40 ml의 Toluene/H2O/Ethanol를 넣고 110℃에서 3시간 동안 교반하였다.Phenyl] -1H-benzo [d] [1,2,3] triazol-4-yl) -6- (3,5-dibromophenyl) triazol-5-ylboronic acid 4.8 g (20.2 mmol), 1.0 g (5 mol%) of Pd (PPh 3) 4, and potassium carbonate 7.0 g Toluene / H 2 of (50.6 mmol) and 80 ml / 40 ml / 40 ml O / Ethanol was added thereto, followed by stirring at 110 ° C for 3 hours.
반응 종료 후, 메틸렌클로라이드를 이용하여 유기층을 분리하고 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 A12(7.4 g, 11.3 mmol, 수율 67%)을 얻었다.After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO 4 . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the target compound A12 (7.4 g, 11.3 mmol, yield 67%).
GC-Mass (이론치: 656.57 g/mol, 측정치: 656 g/mol)GC-Mass (calculated: 656.57 g / mol, measured: 656 g / mol)
1H-NMR: δ 7.41-7.54(m, 13H), 7.61-7.84(m, 6H), 8.09-8.25(m, 7H)1 H-NMR:? 7.41-7.54 (m, 13H), 7.61-7.84 (m, 6H), 8.09-8.25 (m,
[[ 준비예Preparation Example 13] A13의 합성 13] Synthesis of A13
질소 기류 하에서 4-(biphenyl-4-yl)-6-(3,5-dibromophenyl)-2-phenylpyrimidine 9.2 g(16.9 mmol), 1,1-dimethyl-1H-inden-5-ylboronic acid 3.8 g(20.2 mmol), 1.0 g(5 mol%)의 Pd(PPh3)4 및 potassium carbonate 7.0 g(50.6 mmol)와 80 ml/40 ml/40 ml의 Toluene/H2O/Ethanol를 넣고 110℃에서 3시간 동안 교반하였다.9.2 g (16.9 mmol) of 1,1-dimethyl-1H-inden-5-ylboronic acid were added to a solution of 3.8 g of (4- (4-methylphenyl) 20 ml), 1.0 g (5 mol%) of Pd (PPh 3 ) 4 and 7.0 g (50.6 mmol) of potassium carbonate and 80 ml / 40 ml / 40 ml of toluene / H 2 O / Lt; / RTI >
반응 종료 후, 메틸렌클로라이드를 이용하여 유기층을 분리하고 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 A13(6.8 g, 11.3 mmol, 수율 67%)을 얻었다.After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO 4 . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound A13 (6.8 g, 11.3 mmol, yield 67%).
GC-Mass (이론치: 605.56 g/mol, 측정치: 605 g/mol)GC-Mass (theory: 605.56 g / mol, measurement: 605 g / mol)
1H-NMR: δ 1.65(s, 6H), 6.41-6.55(m, 2H), 7.22-7.35(m, 2H), 7.41-7.54(m, 11H), 7.61-7.84(m, 4H), 8.01-8.25(m, 4H)(M, 2H), 7.41-7.54 (m, 11H), 7.61-7.84 (m, 4H), 8.01-7. 8.25 (m, 4H)
[[ 준비예Preparation Example 14] A14의 합성 14] Synthesis of A14
질소 기류 하에서 4-(biphenyl-4-yl)-6-(3,5-dibromophenyl)-2-phenylpyrimidine 9.2 g(16.9 mmol), 3,3-dimethyl-3H-cyclopenta[a]naphthalen-8-ylboronic acid 4.8 g(20.2 mmol), 1.0 g(5 mol%)의 Pd(PPh3)4 및 potassium carbonate 7.0 g(50.6 mmol)와 80 ml/40 ml/40 ml의 Toluene/H2O/Ethanol를 넣고 110℃에서 3시간 동안 교반하였다.9.2 g (16.9 mmol) of 3,3-dimethyl-3H-cyclopenta [a] naphthalen-8-ylboronic acid were added to a solution of 4- (biphenyl-4-yl) -6- (3,5-dibromophenyl) (PPh 3 ) 4 and potassium carbonate (7.0 g, 50.6 mmol) and 80 ml / 40 ml / 40 ml of Toluene / H 2 O / Ethanol were added to a solution of 4.8 g (20.2 mmol) And the mixture was stirred at 110 DEG C for 3 hours.
반응 종료 후, 메틸렌클로라이드를 이용하여 유기층을 분리하고 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 A14(7.4 g, 11.3 mmol, 수율 67%)을 얻었다.After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO 4 . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the desired compound A14 (7.4 g, 11.3 mmol, yield 67%).
GC-Mass (이론치: 655.62 g/mol, 측정치: 655 g/mol)GC-Mass (calculated: 655.62 g / mol, measured: 655 g / mol)
1H-NMR: δ 1.65(s, 6H), 6.41-6.55(m, 2H), 7.01(s, 1H), 7.41-7.54(m, 10H), 7.61-7.89(m, 6H), 8.01-8.29(m, 6H)(M, 2H), 7.01 (s, 1H), 7.41-7.54 (m, 10H), 7.61-7.89 (m, 6H), 8.01-8.29 m, 6H)
[[ 준비예Preparation Example 15] A15의 합성 15] Synthesis of A15
질소 기류 하에서 4-(biphenyl-4-yl)-6-(3,5-dibromophenyl)-2-(pyridin-4-yl)pyrimidine 9.2 g(16.9 mmol), 1,1-dimethyl-1H-inden-5-ylboronic acid 3.8 g(20.2 mmol), 1.0 g(5 mol%)의 Pd(PPh3)4 및 potassium carbonate 7.0 g(50.6 mmol)와 80 ml/40 ml/40 ml의 Toluene/H2O/Ethanol를 넣고 110℃에서 3시간 동안 교반하였다.9.2 g (16.9 mmol) of 1,1-dimethyl-1H-inden-2-yl] pyrimidine was added to a solution of 4- (biphenyl-4- Pd (PPh 3 ) 4 and potassium carbonate (7.0 g, 50.6 mmol) and 1.0 g (5 mol%) of 5-ylboronic acid and 80 ml / 40 ml / 40 ml of toluene / H 2 O / Ethanol was added and the mixture was stirred at 110 ° C for 3 hours.
반응 종료 후, 메틸렌클로라이드를 이용하여 유기층을 분리하고 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 A15(6.9 g, 11.3 mmol, 수율 67%)을 얻었다.After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO 4 . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the target compound A15 (6.9 g, 11.3 mmol, yield 67%).
GC-Mass (이론치: 606.55 g/mol, 측정치: 606 g/mol)GC-Mass (theory: 606.55 g / mol, measurement: 606 g / mol)
1H-NMR: δ 1.65(s, 6H), 6.41-6.55(m, 2H), 7.22-7.33(m, 2H), 7.41-7.54(m, 7H), 7.61-7.84(m, 4H), 8.01-8.25(m, 4H), 8.61-72(m, 3H)2H), 7.41-7.54 (m, 7H), 7.61-7.84 (m, 4H), 8.01-7.54 (m, 2H) 8.25 (m, 4 H), 8.61 - 72 (m, 3 H)
[[ 준비예Preparation Example 16] A16의 합성 16] Synthesis of A16
질소 기류 하에서 2-(3,5-dibromophenyl)-4,6-diphenyl-1,3,5-triazine 7.8 g(16.9 mmol), 1,1-dimethyl-1H-inden-5-ylboronic acid 3.8 g(20.2 mmol), 1.0 g(5 mol%)의 Pd(PPh3)4 및 potassium carbonate 7.0 g(50.6 mmol)와 80 ml/40 ml/40 ml의 Toluene/H2O/Ethanol를 넣고 110℃에서 3시간 동안 교반하였다.3.8 g (16.9 mmol) of 1,1-dimethyl-1 H-inden-5-ylboronic acid were added to a solution of 7.8 g (16.9 mmol) of 2- (3,5-dibromophenyl) 20 ml), 1.0 g (5 mol%) of Pd (PPh 3 ) 4 and 7.0 g (50.6 mmol) of potassium carbonate and 80 ml / 40 ml / 40 ml of toluene / H 2 O / Lt; / RTI >
반응 종료 후, 메틸렌클로라이드를 이용하여 유기층을 분리하고 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 A16(6.0 g, 11.3 mmol, 수율 67%)을 얻었다.After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO 4 . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the target compound A16 (6.0 g, 11.3 mmol, yield 67%).
GC-Mass (이론치: 530.46 g/mol, 측정치: 530 g/mol)GC-Mass (calculated: 530.46 g / mol, measured: 530 g / mol)
1H-NMR: δ 1.65(s, 6H), 6.41-6.55(m, 2H), 7.22-7.33(m, 2H), 7.41-7.51(m, 8H), 7.60-7.84(m, 2H), 8.01-8.25(m, 4H)2H), 7.41-7.51 (m, 8H), 7.60-7.84 (m, 2H), 8.01-7.40 (m, 8.25 (m, 4H)
[[ 준비예Preparation Example 17] A17의 합성 17] Synthesis of A17
질소 기류 하에서 2,4-bis(dibenzo[b,d]furan-2-yl)-6-(3,5-dibromophenyl)-1,3,5-triazine 10.9 g(16.9 mmol), 1,1-dimethyl-1H-inden-5-ylboronic acid 3.8 g(20.2 mmol), 1.0 g(5 mol%)의 Pd(PPh3)4 및 potassium carbonate 7.0 g(50.6 mmol)와 80 ml/40 ml/40 ml의 Toluene/H2O/Ethanol를 넣고 110℃에서 3시간 동안 교반하였다.A solution of 10.9 g (16.9 mmol) of 2,4-bis (dibenzo [b, d] furan-2-yl) -6- (3,5- dibromophenyl) -1,3,5- dimethyl-1H-inden-5- ylboronic acid 3.8 g (20.2 mmol), in 1.0 g (5 mol%) Pd (PPh 3) 4 , and potassium carbonate 7.0 g of (50.6 mmol) and 80 ml / 40 ml / 40 ml Toluene / H 2 O / Ethanol was added thereto, followed by stirring at 110 ° C for 3 hours.
반응 종료 후, 메틸렌클로라이드를 이용하여 유기층을 분리하고 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 A17(8.0 g, 11.3 mmol, 수율 67%)을 얻었다.After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO 4 . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound A17 (8.0 g, 11.3 mmol, yield 67%).
GC-Mass (이론치: 710.62 g/mol, 측정치: 710 g/mol)GC-Mass (calculated: 710.62 g / mol, measured: 710 g / mol)
1H-NMR: δ 1.65(s, 6H), 6.41-6.55(m, 2H), 7.22-7.37(m, 5H), 7.45-7.51(m, 2H), 7.60-7.89(m, 13H)(M, 5H), 7.45-7.51 (m, 2H), 7.60-7.89 (m, 13H)
[[ 준비예Preparation Example 18] A18의 합성 18] Synthesis of A18
질소 기류 하에서 4-(biphenyl-4-yl)-6-(3,5-dibromophenyl)-2-phenylpyrimidine 9.2 g(16.9 mmol), 1,1-diphenyl-1H-inden-5-ylboronic acid 6.3 g(20.2 mmol), 1.0 g(5 mol%)의 Pd(PPh3)4 및 potassium carbonate 7.0 g(50.6 mmol)와 80 ml/40 ml/40 ml의 Toluene/H2O/Ethanol를 넣고 110℃에서 3시간 동안 교반하였다.A mixture of 9.2 g (16.9 mmol) of 4- (biphenyl-4-yl) -6- (3,5-dibromophenyl) -2-phenylpyrimidine and 6.3 g of 1,1-diphenyl-1H- inden- 20 ml), 1.0 g (5 mol%) of Pd (PPh 3 ) 4 and 7.0 g (50.6 mmol) of potassium carbonate and 80 ml / 40 ml / 40 ml of toluene / H 2 O / Lt; / RTI >
반응 종료 후, 메틸렌클로라이드를 이용하여 유기층을 분리하고 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 A18(8.2 g, 11.3 mmol, 수율 67%)을 얻었다.After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO 4 . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the desired compound A18 (8.2 g, 11.3 mmol, yield 67%).
GC-Mass (이론치: 729.70 g/mol, 측정치: 729 g/mol)GC-Mass (theory: 729.70 g / mol, measurement: 729 g / mol)
1H-NMR: δ 6.41-6.55(m, 2H), 7.22-7.37(m, 12H), 7.45-7.51(m, 10H), 7.60-7.89(m, 4H), 8.01-8.25(m, 5H)(M, 2H), 7.22-7.37 (m, 12H), 7.45-7.51 (m, 10H), 7.60-7.89 (m, 4H), 8.01-8.25
[[ 합성예Synthetic example 1] One] R1R1 의 합성Synthesis of
질소 기류 하에서 A1 6.4 g(11.0 mmol), 1H-indole 1.5 g(13.2 mmol), 0.5 g(5 mol%)의 Pd2(dba)3, tri-tert-butylphosphine 0.1 g(0.6 mmol) 및 Sodium tert-butoxide 3.2 g(32.9 mmol)와 100 ml의 Toluene을 넣고 110℃에서 4시간 동안 교반하였다.In a nitrogen stream A1 6.4 g (11.0 mmol), 1H-indole 1.5 g (13.2 mmol), 0.5 g (5 mol%) of Pd 2 (dba) 3, tri- tert -butylphosphine 0.1 g (0.6 mmol) and Sodium tert -butoxide (3.2 g, 32.9 mmol) and 100 ml of toluene were placed, and the mixture was stirred at 110 DEG C for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R1 5.1 g(8.2 mmol, 수율 75%)을 얻었다.After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO 4 . The residue was purified by column chromatography to obtain 5.1 g of the objective compound R1 (8.2 mmol, yield 75%).
GC-Mass (이론치: 615.72 g/mol, 측정치: 615 g/mol)GC-Mass (calculated: 615.72 g / mol, measured: 615 g / mol)
[[ 합성예Synthetic example 2] 2] R3R3 의 합성Synthesis of
질소 기류 하에서 A2 6.9 g(11.0 mmol), 1H-indole 1.5 g(13.2 mmol), 0.5 g(5 mol%)의 Pd2(dba)3, tri-tert-butylphosphine 0.1 g(0.6 mmol) 및 Sodium tert-butoxide 3.2 g(32.9 mmol)와 100 ml의 Toluene을 넣고 110℃에서 4시간 동안 교반하였다.In a nitrogen stream A2 6.9 g (11.0 mmol), 1H-indole 1.5 g (13.2 mmol), 0.5 g (5 mol%) of Pd 2 (dba) 3, tri- tert -butylphosphine 0.1 g (0.6 mmol) and Sodium tert -butoxide (3.2 g, 32.9 mmol) and 100 ml of toluene were placed, and the mixture was stirred at 110 DEG C for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R3 5.5 g(8.2 mmol, 수율 75%)을 얻었다.After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO 4 . The residue was purified by column chromatography to obtain 5.5 g of the objective compound R3 (8.2 mmol, yield 75%).
GC-Mass (이론치: 665.78 g/mol, 측정치: 665 g/mol)GC-Mass (calculated: 665.78 g / mol, measured: 665 g / mol)
[[ 합성예Synthetic example 3] 3] R4R4 의 합성Synthesis of
질소 기류 하에서 A3 7.2 g(11.0 mmol), 1H-indole 1.5 g(13.2 mmol), 0.5 g(5 mol%)의 Pd2(dba)3, tri-tert-butylphosphine 0.1 g(0.6 mmol) 및 Sodium tert-butoxide 3.2 g(32.9 mmol)와 100 ml의 Toluene을 넣고 110℃에서 4시간 동안 교반하였다.In a nitrogen stream A3 7.2 g (11.0 mmol), 1H-indole 1.5 g (13.2 mmol), 0.5 g (5 mol%) of Pd 2 (dba) 3, tri- tert -butylphosphine 0.1 g (0.6 mmol) and Sodium tert -butoxide (3.2 g, 32.9 mmol) and 100 ml of toluene were placed, and the mixture was stirred at 110 DEG C for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R4 5.7 g(8.2 mmol, 수율 75%)을 얻었다.After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO 4 . The residue was purified by column chromatography to obtain 5.7 g (8.2 mmol, yield 75%) of the target compound R4.
GC-Mass (이론치: 693.80 g/mol, 측정치: 693 g/mol)GC-Mass (calculated: 693.80 g / mol, measured: 693 g / mol)
[[ 합성예Synthetic example 4] 4] R5R5 의 합성Synthesis of
질소 기류 하에서 A4 5.5 g(11.0 mmol), 1H-indole 1.5 g(13.2 mmol), 0.5 g(5 mol%)의 Pd2(dba)3, tri-tert-butylphosphine 0.1 g(0.6 mmol) 및 Sodium tert-butoxide 3.2 g(32.9 mmol)와 100 ml의 Toluene을 넣고 110℃에서 4시간 동안 교반하였다.1.5 g (13.2 mmol) of 1H-indole, 0.5 g (5 mol%) of Pd 2 (dba) 3 , 0.1 g of tri- tert- butylphosphine (0.6 mmol) and Sodium tert -butoxide (3.2 g, 32.9 mmol) and 100 ml of toluene were placed, and the mixture was stirred at 110 DEG C for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R5 4.4 g(8.2 mmol, 수율 75%)을 얻었다.After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO 4 . The residue was purified by column chromatography to obtain 4.4 g (8.2 mmol, yield 75%) of the target compound R5.
GC-Mass (이론치: 540.62 g/mol, 측정치: 540 g/mol)GC-Mass (calculated: 540.62 g / mol, measured: 540 g / mol)
[[ 합성예Synthetic example 5] 5] R6R6 의 합성Synthesis of
질소 기류 하에서 A5 7.5 g(11.0 mmol), 1H-indole 1.5 g(13.2 mmol), 0.5 g(5 mol%)의 Pd2(dba)3, tri-tert-butylphosphine 0.1 g(0.6 mmol) 및 Sodium tert-butoxide 3.2 g(32.9 mmol)와 100 ml의 Toluene을 넣고 110℃에서 4시간 동안 교반하였다.In a nitrogen atmosphere A5 7.5 g (11.0 mmol), 1H-indole 1.5 g (13.2 mmol), 0.5 g (5 mol%) of Pd 2 (dba) 3, tri- tert -butylphosphine 0.1 g (0.6 mmol) and Sodium tert -butoxide (3.2 g, 32.9 mmol) and 100 ml of toluene were placed, and the mixture was stirred at 110 DEG C for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R6 5.9 g(8.2 mmol, 수율 75%)을 얻었다.After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO 4 . The residue was purified by column chromatography to obtain 5.9 g (8.2 mmol, yield 75%) of the desired compound R6.
GC-Mass (이론치: 720.77 g/mol, 측정치: 720 g/mol)GC-Mass (calculated: 720.77 g / mol, measured: 720 g / mol)
[[ 합성예6Synthesis Example 6 ] ] R7R7 의 합성Synthesis of
질소 기류 하에서 A6 7.2 g(11.0 mmol), 1H-indole 1.5 g(13.2 mmol), 0.5 g(5 mol%)의 Pd2(dba)3, tri-tert-butylphosphine 0.1 g(0.6 mmol) 및 Sodium tert-butoxide 3.2 g(32.9 mmol)와 100 ml의 Toluene을 넣고 110℃에서 4시간 동안 교반하였다.In a nitrogen atmosphere A6 7.2 g (11.0 mmol), 1H-indole 1.5 g (13.2 mmol), 0.5 g (5 mol%) of Pd 2 (dba) 3, tri- tert -butylphosphine 0.1 g (0.6 mmol) and Sodium tert -butoxide (3.2 g, 32.9 mmol) and 100 ml of toluene were placed, and the mixture was stirred at 110 DEG C for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R7 5.7 g(8.2 mmol, 수율 75%)을 얻었다.After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO 4 . The residue was purified by column chromatography to obtain 5.7 g (8.2 mmol, yield 75%) of the target compound R7.
GC-Mass (이론치: 691.82 g/mol, 측정치: 691 g/mol)GC-Mass (calculated: 691.82 g / mol, measured: 691 g / mol)
[[ 합성예Synthetic example 7] 7] R11R11 의 합성Synthesis of
질소 기류 하에서 A1 6.4 g(11.0 mmol), 1H-indazole 1.6 g(13.2 mmol), 0.5 g(5 mol%)의 Pd2(dba)3, tri-tert-butylphosphine 0.1 g(0.6 mmol) 및 Sodium tert-butoxide 3.2 g(32.9 mmol)와 100 ml의 Toluene을 넣고 110℃에서 4시간 동안 교반하였다.In a nitrogen stream A1 6.4 g (11.0 mmol), 1H-indazole 1.6 g (13.2 mmol), 0.5 g (5 mol%) of Pd 2 (dba) 3, tri- tert -butylphosphine 0.1 g (0.6 mmol) and Sodium tert -butoxide (3.2 g, 32.9 mmol) and 100 ml of toluene were placed, and the mixture was stirred at 110 DEG C for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R11 4.9 g(8.0 mmol, 수율 73%)을 얻었다.After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO 4 . The residue was purified by column chromatography to obtain 4.9 g (8.0 mmol, yield 73%) of the desired compound R11.
GC-Mass (이론치: 616.71 g/mol, 측정치: 616 g/mol)GC-Mass (theory: 616.71 g / mol, measured: 616 g / mol)
[[ 합성예Synthetic example 8] 8] R13R13 의 합성Synthesis of
질소 기류 하에서 A2 6.9 g(11.0 mmol), 1H-indazole 1.6 g(13.2 mmol), 0.5 g(5 mol%)의 Pd2(dba)3, tri-tert-butylphosphine 0.1 g(0.6 mmol) 및 Sodium tert-butoxide 3.2 g(32.9 mmol)와 100 ml의 Toluene을 넣고 110℃에서 4시간 동안 교반하였다.In a nitrogen stream A2 6.9 g (11.0 mmol), 1H-indazole 1.6 g (13.2 mmol), 0.5 g (5 mol%) of Pd 2 (dba) 3, tri- tert -butylphosphine 0.1 g (0.6 mmol) and Sodium tert -butoxide (3.2 g, 32.9 mmol) and 100 ml of toluene were placed, and the mixture was stirred at 110 DEG C for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R13 5.3 g(8.0 mmol, 수율 73%)을 얻었다.After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO 4 . The residue was purified by column chromatography to obtain 5.3 g (8.0 mmol, yield 73%) of the desired compound R13.
GC-Mass (이론치: 666.77 g/mol, 측정치: 666 g/mol)GC-Mass (calculated: 666.77 g / mol, measured: 666 g / mol)
[[ 합성예Synthetic example 9] 9] R14R14 의 합성Synthesis of
질소 기류 하에서 A3 7.2 g(11.0 mmol), 1H-indazole 1.6 g(13.2 mmol), 0.5 g(5 mol%)의 Pd2(dba)3, tri-tert-butylphosphine 0.1 g(0.6 mmol) 및 Sodium tert-butoxide 3.2 g(32.9 mmol)와 100 ml의 Toluene을 넣고 110℃에서 4시간 동안 교반하였다.A mixture of 7.2 g (11.0 mmol) of A3, 1.6 g (13.2 mmol) of 1H-indazole, 0.5 g (5 mol%) of Pd 2 (dba) 3 , tri- tert- butylphosphine 0.1 g -butoxide (3.2 g, 32.9 mmol) and 100 ml of toluene were placed, and the mixture was stirred at 110 DEG C for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R14 5.6 g(8.0 mmol, 수율 73%)을 얻었다.After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO 4 . The residue was purified by column chromatography to obtain 5.6 g (8.0 mmol, yield 73%) of the target compound R14.
GC-Mass (이론치: 694.78 g/mol, 측정치: 694 g/mol)GC-Mass (calculated: 694.78 g / mol, measured: 694 g / mol)
[[ 합성예Synthetic example 10] 10] R15R15 의 합성Synthesis of
질소 기류 하에서 A4 5.5 g(11.0 mmol), 1H-indazole 1.6 g(13.2 mmol), 0.5 g(5 mol%)의 Pd2(dba)3, tri-tert-butylphosphine 0.1 g(0.6 mmol) 및 Sodium tert-butoxide 3.2 g(32.9 mmol)와 100 ml의 Toluene을 넣고 110℃에서 4시간 동안 교반하였다.In a nitrogen atmosphere A4 5.5 g (11.0 mmol), 1H-indazole 1.6 g (13.2 mmol), 0.5 g (5 mol%) of Pd 2 (dba) 3, tri- tert -butylphosphine 0.1 g (0.6 mmol) and Sodium tert -butoxide (3.2 g, 32.9 mmol) and 100 ml of toluene were placed, and the mixture was stirred at 110 DEG C for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R15 4.3 g(8.0 mmol, 수율 73%)을 얻었다After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO 4 . The residue was purified by column chromatography to obtain 4.3 g (8.0 mmol, yield 73%) of the desired compound R15
GC-Mass (이론치: 541.60 g/mol, 측정치: 541 g/mol)GC-Mass (calculated: 541.60 g / mol, measured: 541 g / mol)
[[ 합성예Synthetic example 11] 11] R16R16 의 합성Synthesis of
질소 기류 하에서 A5 7.5 g(11.0 mmol), 1H-indazole 1.6 g(13.2 mmol), 0.5 g(5 mol%)의 Pd2(dba)3, tri-tert-butylphosphine 0.1 g(0.6 mmol) 및 Sodium tert-butoxide 3.2 g(32.9 mmol)와 100 ml의 Toluene을 넣고 110℃에서 4시간 동안 교반하였다.In a nitrogen atmosphere A5 7.5 g (11.0 mmol), 1H-indazole 1.6 g (13.2 mmol), 0.5 g (5 mol%) of Pd 2 (dba) 3, tri- tert -butylphosphine 0.1 g (0.6 mmol) and Sodium tert -butoxide (3.2 g, 32.9 mmol) and 100 ml of toluene were placed, and the mixture was stirred at 110 DEG C for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R16 5.8 g(8.0 mmol, 수율 73%)을 얻었다.After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO 4 . The residue was purified by column chromatography to obtain 5.8 g (8.0 mmol, yield 73%) of the target compound R16.
GC-Mass (이론치: 721.76 g/mol, 측정치: 721 g/mol)GC-Mass (calculated: 721.76 g / mol, measured: 721 g / mol)
[[ 합성예12Synthesis Example 12 ] A17의 합성] Synthesis of A17
질소 기류 하에서 A6 7.2 g(11.0 mmol), 1H-indazole 1.6 g(13.2 mmol), 0.5 g(5 mol%)의 Pd2(dba)3, tri-tert-butylphosphine 0.1 g(0.6 mmol) 및 Sodium tert-butoxide 3.2 g(32.9 mmol)와 100 ml의 Toluene을 넣고 110℃에서 4시간 동안 교반하였다.In a nitrogen atmosphere A6 7.2 g (11.0 mmol), 1H-indazole 1.6 g (13.2 mmol), 0.5 g (5 mol%) of Pd 2 (dba) 3, tri- tert -butylphosphine 0.1 g (0.6 mmol) and Sodium tert -butoxide (3.2 g, 32.9 mmol) and 100 ml of toluene were placed, and the mixture was stirred at 110 DEG C for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R17 5.5 g(8.0 mmol, 수율 73%)을 얻었다.After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO 4 . The residue was purified by column chromatography to obtain 5.5 g (8.0 mmol, yield 73%) of the target compound R17.
GC-Mass (이론치: 692.81 g/mol, 측정치: 692 g/mol)GC-Mass (calculated: 692.81 g / mol, measured: 692 g / mol)
[[ 합성예Synthetic example 13] 13] R21R21 의 합성Synthesis of
질소 기류 하에서 A1 6.4 g(11.0 mmol), 1H-benzo[d][1,2,3]triazole 1.6 g(13.2 mmol), 0.5 g(5 mol%)의 Pd2(dba)3, tri-tert-butylphosphine 0.1 g(0.6 mmol) 및 Sodium tert-butoxide 3.2 g(32.9 mmol)와 100 ml의 Toluene을 넣고 110℃에서 4시간 동안 교반하였다.In a nitrogen stream A1 6.4 g (11.0 mmol), 1H-benzo [d] [1,2,3] triazole 1.6 g (13.2 mmol), 0.5 g (5 mol%) of Pd 2 (dba) 3, tri- tert -butylphosphine (0.1 g, 0.6 mmol), sodium tert-butoxide (3.2 g, 32.9 mmol) and 100 ml of toluene were placed and stirred at 110 ° C for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R21 4.9 g(8.0 mmol, 수율 73%)을 얻었다.After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO 4 . The residue was purified by column chromatography to obtain 4.9 g (8.0 mmol, yield 73%) of the target compound R21.
GC-Mass (이론치: 617.70 g/mol, 측정치: 617 g/mol)GC-Mass (calculated: 617.70 g / mol, measured: 617 g / mol)
[[ 합성예Synthetic example 14] 14] R23R23 의 합성Synthesis of
질소 기류 하에서 A2 6.9 g(11.0 mmol), 1H-benzo[d][1,2,3]triazole 1.6 g(13.2 mmol), 0.5 g(5 mol%)의 Pd2(dba)3, tri-tert-butylphosphine 0.1 g(0.6 mmol) 및 Sodium tert-butoxide 3.2 g(32.9 mmol)와 100 ml의 Toluene을 넣고 110℃에서 4시간 동안 교반하였다.In a nitrogen stream A2 6.9 g (11.0 mmol), 1H-benzo [d] [1,2,3] triazole 1.6 g (13.2 mmol), 0.5 g (5 mol%) of Pd 2 (dba) 3, tri- tert -butylphosphine (0.1 g, 0.6 mmol), sodium tert-butoxide (3.2 g, 32.9 mmol) and 100 ml of toluene were placed and stirred at 110 ° C for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R23, 5.3g(8.0mmol, 수율 73%)을 얻었다.After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO 4 . The residue was purified by column chromatography to obtain 5.3 g (8.0 mmol, yield 73%) of the target compound R23.
GC-Mass (이론치: 667.76 g/mol, 측정치: 667 g/mol)GC-Mass (calculated: 667.76 g / mol, measured: 667 g / mol)
[[ 합성예Synthetic example 15] 15] R24R24 의 합성Synthesis of
질소 기류 하에서 A3 7.2 g(11.0 mmol), 1H-benzo[d][1,2,3]triazole 1.6 g(13.2 mmol), 0.5 g(5 mol%)의 Pd2(dba)3, tri-tert-butylphosphine 0.1 g(0.6 mmol) 및 Sodium tert-butoxide 3.2 g(32.9 mmol)와 100 ml의 Toluene을 넣고 110℃에서 4시간 동안 교반하였다.In a nitrogen stream A3 7.2 g (11.0 mmol), 1H-benzo [d] [1,2,3] triazole 1.6 g (13.2 mmol), 0.5 g (5 mol%) of Pd 2 (dba) 3, tri- tert -butylphosphine (0.1 g, 0.6 mmol), sodium tert-butoxide (3.2 g, 32.9 mmol) and 100 ml of toluene were placed and stirred at 110 ° C for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R24 5.6 g(8.0 mmol, 수율 73%)을 얻었다.After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO 4 . The residue was purified by column chromatography to obtain 5.6 g (8.0 mmol, yield 73%) of the target compound R24.
GC-Mass (이론치: 695.77 g/mol, 측정치: 695 g/mol)GC-Mass (calculated: 695.77 g / mol, measured: 695 g / mol)
[[ 합성예Synthetic example 16] 16] R25R25 의 합성Synthesis of
질소 기류 하에서 A4 5.5 g(11.0 mmol), 1H-benzo[d][1,2,3]triazole 1.6 g(13.2 mmol), 0.5 g(5 mol%)의 Pd2(dba)3, tri-tert-butylphosphine 0.1 g(0.6 mmol) 및 Sodium tert-butoxide 3.2 g(32.9 mmol)와 100 ml의 Toluene을 넣고 110℃에서 4시간 동안 교반하였다.In a nitrogen atmosphere A4 5.5 g (11.0 mmol), 1H-benzo [d] [1,2,3] triazole 1.6 g (13.2 mmol), 0.5 g Pd 2 (dba) of (5 mol%) 3, tri- tert -butylphosphine (0.1 g, 0.6 mmol), sodium tert-butoxide (3.2 g, 32.9 mmol) and 100 ml of toluene were placed and stirred at 110 ° C for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R25 4.3 g(8.0 mmol, 수율 73%)을 얻었다.After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO 4 . The residue was purified by column chromatography to obtain 4.3 g (8.0 mmol, yield 73%) of the target compound R25.
GC-Mass (이론치: 542.59 g/mol, 측정치: 542 g/mol)GC-Mass (calculated: 542.59 g / mol, measured: 542 g / mol)
[[ 합성예Synthetic example 17] 17] R26R26 의 합성Synthesis of
질소 기류 하에서 A5 7.5 g(11.0 mmol), 1H-benzo[d][1,2,3]triazole 1.6 g(13.2 mmol), 0.5 g(5 mol%)의 Pd2(dba)3, tri-tert-butylphosphine 0.1 g(0.6 mmol) 및 Sodium tert-butoxide 3.2 g(32.9 mmol)와 100 ml의 Toluene을 넣고 110℃에서 4시간 동안 교반하였다.In a nitrogen atmosphere A5 7.5 g (11.0 mmol), 1H-benzo [d] [1,2,3] triazole 1.6 g (13.2 mmol), 0.5 g (5 mol%) of Pd 2 (dba) 3, tri- tert -butylphosphine (0.1 g, 0.6 mmol), sodium tert-butoxide (3.2 g, 32.9 mmol) and 100 ml of toluene were placed and stirred at 110 ° C for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R26 5.8 g(8.0 mmol, 수율 73%)을 얻었다.After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO 4 . The residue was purified by column chromatography to obtain 5.8 g (8.0 mmol, yield 73%) of the objective compound R26.
GC-Mass (이론치: 722.75 g/mol, 측정치: 722 g/mol)GC-Mass (calculated: 722.75 g / mol, measured: 722 g / mol)
[[ 합성예Synthetic example 18] 18] R27R27 의 합성Synthesis of
질소 기류 하에서 A6 7.2 g(11.0 mmol), 1H-benzo[d][1,2,3]triazole 1.6 g(13.2 mmol), 0.5 g(5 mol%)의 Pd2(dba)3, tri-tert-butylphosphine, 0.1 g(0.6 mmol) 및 Sodium tert-butoxide 3.2 g(32.9 mmol)와 100 ml의 Toluene을 넣고 110℃에서 4시간 동안 교반하였다.In a nitrogen atmosphere A6 7.2 g (11.0 mmol), 1H-benzo [d] [1,2,3] triazole 1.6 g (13.2 mmol), 0.5 g (5 mol%) of Pd 2 (dba) 3, tri- tert -butylphosphine, 0.1 g (0.6 mmol) of sodium tert-butoxide, 32.9 mmol of sodium tert-butoxide, and 100 ml of toluene, and the mixture was stirred at 110 ° C for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R27 5.6 g(8.0 mmol, 수율 73%)을 얻었다.After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO 4 . The residue was purified by column chromatography to obtain 5.6 g (8.0 mmol, yield 73%) of the objective compound R27.
GC-Mass (이론치: 693.80 g/mol, 측정치: 693 g/mol)GC-Mass (calculated: 693.80 g / mol, measured: 693 g / mol)
[[ 합성예Synthetic example 19] 19] R31R31 의 합성Synthesis of
질소 기류 하에서 A1 6.4 g(11.0 mmol), 9-benzofuran-5-ylboronic acid 2.1 g(13.2 mmol), 0.6 g(5 mol%)의 Pd(PPh3)4 및 potassium carbonate 4.5 g(32.9 mmol)와 80 ml/40 ml/40 ml의 Toluene/H2O/Ethanol를 넣고 110℃에서 3시간 동안 교반하였다.In a nitrogen stream A1 6.4 g (11.0 mmol), 9-benzofuran-5-ylboronic acid 2.1 g (13.2 mmol), Pd of 0.6 g (5 mol%) ( PPh 3) 4 , and potassium carbonate 4.5 g (32.9 mmol) and 80 ml / 40 ml / 40 ml of Toluene / H 2 O / Ethanol was added and the mixture was stirred at 110 ° C for 3 hours.
반응 종료 후, 메틸렌클로라이드를 이용하여 유기층을 분리하고 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 R31(4.4 g, 7.1 mmol, 수율 65%)을 얻었다.After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO 4 . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound R31 (4.4 g, 7.1 mmol, yield 65%).
GC-Mass (이론치: 616.71 g/mol, 측정치: 616 g/mol)GC-Mass (theory: 616.71 g / mol, measured: 616 g / mol)
[[ 합성예Synthetic example 20] 20] R33R33 의 합성Synthesis of
질소 기류 하에서 A2 6.9 g(11.0 mmol), 9-benzofuran-5-ylboronic acid 2.1 g(13.2 mmol), 0.6 g(5 mol%)의 Pd(PPh3)4 및 potassium carbonate 4.5 g(32.9 mmol)와 80 ml/40 ml/40 ml의 Toluene/H2O/Ethanol를 넣고 110℃에서 3시간 동안 교반하였다.In a nitrogen stream A2 6.9 g (11.0 mmol), 9-benzofuran-5-ylboronic acid 2.1 g (13.2 mmol), 0.6 g (5 mol%) of Pd (PPh 3) 4, and potassium carbonate 4.5 g (32.9 mmol) and 80 ml / 40 ml / 40 ml of Toluene / H 2 O / Ethanol was added and the mixture was stirred at 110 ° C for 3 hours.
반응 종료 후, 메틸렌클로라이드를 이용하여 유기층을 분리하고 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 R33(4.8 g, 7.1 mmol, 수율 65%)을 얻었다.After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO 4 . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound R33 (4.8 g, 7.1 mmol, yield 65%).
GC-Mass (이론치: 666.77 g/mol, 측정치: 666 g/mol)GC-Mass (calculated: 666.77 g / mol, measured: 666 g / mol)
[[ 합성예Synthetic example 21] 21] R34R34 의 합성Synthesis of
질소 기류 하에서 A3 7.2 g(11.0 mmol), 9-benzofuran-5-ylboronic acid 2.1 g(13.2 mmol), 0.6 g(5 mol%)의 Pd(PPh3)4 및 potassium carbonate 4.5 g(32.9 mmol)와 80 ml/40 ml/40 ml의 Toluene/H2O/Ethanol를 넣고 110℃에서 3시간 동안 교반하였다.In a nitrogen stream A3 7.2 g (11.0 mmol), 9-benzofuran-5-ylboronic acid 2.1 g (13.2 mmol), 0.6 g (5 mol%) of Pd (PPh 3) 4, and potassium carbonate 4.5 g (32.9 mmol) and 80 ml / 40 ml / 40 ml of Toluene / H 2 O / Ethanol was added and the mixture was stirred at 110 ° C for 3 hours.
반응 종료 후, 메틸렌클로라이드를 이용하여 유기층을 분리하고 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 R34(5.0 g, 7.1 mmol, 수율 65%)을 얻었다.After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO 4 . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound R34 (5.0 g, 7.1 mmol, yield 65%).
GC-Mass (이론치: 694.78 g/mol, 측정치: 694 g/mol)GC-Mass (calculated: 694.78 g / mol, measured: 694 g / mol)
[[ 합성예Synthetic example 22] 22] R35R35 의 합성Synthesis of
질소 기류 하에서 A4 5.5 g(11.0 mmol), 9-benzofuran-5-ylboronic acid 2.1 g(13.2 mmol), 0.6 g(5 mol%)의 Pd(PPh3)4 및 potassium carbonate 4.5 g(32.9 mmol)와 80 ml/40 ml/40 ml의 Toluene/H2O/Ethanol를 넣고 110℃에서 3시간 동안 교반하였다.In a nitrogen atmosphere A4 5.5 g (11.0 mmol), 9-benzofuran-5-ylboronic acid 2.1 g (13.2 mmol), 0.6 g (5 mol%) of Pd (PPh 3) 4, and potassium carbonate 4.5 g (32.9 mmol) and 80 ml / 40 ml / 40 ml of Toluene / H 2 O / Ethanol was added and the mixture was stirred at 110 ° C for 3 hours.
반응 종료 후, 메틸렌클로라이드를 이용하여 유기층을 분리하고 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 R35(3.9 g, 7.1 mmol, 수율 65%)을 얻었다.After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO 4 . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound R35 (3.9 g, 7.1 mmol, yield 65%).
GC-Mass (이론치: 541.60 g/mol, 측정치: 541 g/mol)GC-Mass (calculated: 541.60 g / mol, measured: 541 g / mol)
[[ 합성예Synthetic example 23] 23] R36R36 의 합성Synthesis of
질소 기류 하에서 A5 7.5 g(11.0 mmol), 9 benzofuran-5-ylboronic acid 2.1 g(13.2 mmol), 0.6 g(5 mol%)의 Pd(PPh3)4 및 potassium carbonate 4.5 g(32.9 mmol)와 80 ml/40 ml/40 ml의 Toluene/H2O/Ethanol를 넣고 110℃에서 3시간 동안 교반하였다.In a nitrogen atmosphere A5 7.5 g (11.0 mmol), 9 benzofuran-5-ylboronic acid 2.1 g (13.2 mmol), 0.6 g (5 mol%) of Pd (PPh 3) 4, and potassium carbonate 4.5 g (32.9 mmol) and 80 ml / 40 ml / 40 ml of Toluene / H 2 O / Ethanol, and the mixture was stirred at 110 ° C for 3 hours.
반응 종료 후, 메틸렌클로라이드를 이용하여 유기층을 분리하고 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 R36(5.1 g, 7.1 mmol, 수율 65%)을 얻었다.After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO 4 . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the target compound R36 (5.1 g, 7.1 mmol, yield 65%).
GC-Mass (이론치: 721.76 g/mol, 측정치: 721 g/mol)GC-Mass (calculated: 721.76 g / mol, measured: 721 g / mol)
[[ 합성예Synthetic example 24] 24] R37R37 의 합성Synthesis of
질소 기류 하에서 A6 7.2 g(11.0 mmol), 9-benzofuran-5-ylboronic acid 2.1 g(13.2 mmol), 0.6 g(5 mol%)의 Pd(PPh3)4 및 potassium carbonate 4.5 g(32.9 mmol)와 80 ml/40 ml/40 ml의 Toluene/H2O/Ethanol를 넣고 110℃에서 3시간 동안 교반하였다.In a nitrogen atmosphere A6 7.2 g (11.0 mmol), 9-benzofuran-5-ylboronic acid 2.1 g (13.2 mmol), 0.6 g (5 mol%) of Pd (PPh 3) 4, and potassium carbonate 4.5 g (32.9 mmol) and 80 ml / 40 ml / 40 ml of Toluene / H 2 O / Ethanol was added and the mixture was stirred at 110 ° C for 3 hours.
반응 종료 후, 메틸렌클로라이드를 이용하여 유기층을 분리하고 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 R37(4.9 g, 7.1mmol, 수율 65%)을 얻었다.After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO 4 . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound R37 (4.9 g, 7.1 mmol, yield 65%).
GC-Mass (이론치: 692.80 g/mol, 측정치: 692 g/mol)GC-Mass (calculated: 692.80 g / mol, measured: 692 g / mol)
[[ 합성예Synthetic example 25] 25] R41R41 의 합성Synthesis of
질소 기류 하에서 A1 6.4 g(11.0 mmol), 1,1-dimethyl-1H-inden-5-ylboronic acid 2.5 g(13.2 mmol), 0.6 g(5 mol%)의 Pd(PPh3)4 및 potassium carbonate 4.5 g(32.9 mmol)와 80 ml/40 ml/40 ml의 Toluene/H2O/Ethanol를 넣고 110℃에서 3시간 동안 교반하였다.In a nitrogen stream A1 6.4 g (11.0 mmol), 1,1-dimethyl-1H-inden-5-ylboronic acid 2.5 g (13.2 mmol), 0.6 g (5 mol%) of Pd (PPh 3) 4, and potassium carbonate 4.5 g (32.9 mmol) and 80 ml / 40 ml / 40 ml of toluene / H 2 O / ethanol were added and stirred at 110 ° C for 3 hours.
반응 종료 후, 메틸렌클로라이드를 이용하여 유기층을 분리하고 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 R41(4.6 g, 7.1 mmol, 수율 65%)을 얻었다.After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO 4 . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the target compound R41 (4.6 g, 7.1 mmol, yield 65%).
GC-Mass (이론치: 642.79 g/mol, 측정치: 642 g/mol)GC-Mass (calculated: 642.79 g / mol, measured: 642 g / mol)
[[ 합성예Synthetic example 26] 26] R43R43 의 합성Synthesis of
질소 기류 하에서 A2 6.9 g(11.0 mmol), 1,1-dimethyl-1H-inden-5-ylboronic acid 2.5 g(13.2 mmol), 0.6 g(5 mol%)의 Pd(PPh3)4 및 potassium carbonate 4.5 g(32.9 mmol)와 80 ml/40 ml/40 ml의 Toluene/H2O/Ethanol를 넣고 110℃에서 3시간 동안 교반하였다.In a nitrogen stream A2 6.9 g (11.0 mmol), 1,1-dimethyl-1H-inden-5-ylboronic acid 2.5 g (13.2 mmol), 0.6 g (5 mol%) of Pd (PPh 3) 4, and potassium carbonate 4.5 g (32.9 mmol) and 80 ml / 40 ml / 40 ml of toluene / H 2 O / ethanol were added and stirred at 110 ° C for 3 hours.
반응 종료 후, 메틸렌클로라이드를 이용하여 유기층을 분리하고 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 R43(4.9 g, 7.1 mmol, 수율 65%)을 얻었다.After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO 4 . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the target compound R43 (4.9 g, 7.1 mmol, yield 65%).
GC-Mass (이론치: 692.85 g/mol, 측정치: 692 g/mol)GC-Mass (calculated: 692.85 g / mol, measured: 692 g / mol)
[[ 합성예Synthetic example 27] 27] R44R44 의 합성Synthesis of
질소 기류 하에서 A3 7.2 g(11.0 mmol), 1,1-dimethyl-1H-inden-5-ylboronic acid 2.5 g(13.2 mmol), 0.6 g(5 mol%)의 Pd(PPh3)4 및 potassium carbonate 4.5 g(32.9 mmol)와 80 ml/40 ml/40 ml의 Toluene/H2O/Ethanol를 넣고 110℃에서 3시간 동안 교반하였다.In a nitrogen stream A3 7.2 g (11.0 mmol), 1,1-dimethyl-1H-inden-5-ylboronic acid 2.5 g (13.2 mmol), 0.6 g (5 mol%) of Pd (PPh 3) 4, and potassium carbonate 4.5 g (32.9 mmol) and 80 ml / 40 ml / 40 ml of toluene / H 2 O / ethanol were added and stirred at 110 ° C for 3 hours.
반응 종료 후, 메틸렌클로라이드를 이용하여 유기층을 분리하고 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 R44(5.1 g, 7.1 mmol, 수율 65%)을 얻었다.After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO 4 . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the target compound R44 (5.1 g, 7.1 mmol, yield 65%).
GC-Mass (이론치: 720.86 g/mol, 측정치: 720 g/mol)GC-Mass (calculated: 720.86 g / mol, measured: 720 g / mol)
[[ 합성예Synthetic example 28] 28] R45R45 의 합성Synthesis of
질소 기류 하에서 A4 5.5 g(11.0 mmol), 1,1-dimethyl-1H-inden-5-ylboronic acid 2.5 g(13.2 mmol), 0.6 g(5 mol%)의 Pd(PPh3)4 및 potassium carbonate 4.5 g(32.9 mmol)와 80 ml/40 ml/40 ml의 Toluene/H2O/Ethanol를 넣고 110℃에서 3시간 동안 교반하였다.In a nitrogen atmosphere A4 5.5 g (11.0 mmol), 1,1-dimethyl-1H-inden-5-ylboronic acid 2.5 g (13.2 mmol), 0.6 g (5 mol%) of Pd (PPh 3) 4, and potassium carbonate 4.5 g (32.9 mmol) and 80 ml / 40 ml / 40 ml of toluene / H 2 O / ethanol were added and stirred at 110 ° C for 3 hours.
반응 종료 후, 메틸렌클로라이드를 이용하여 유기층을 분리하고 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 R45(4.0 g, 7.1 mmol, 수율 65%)을 얻었다.After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO 4 . After removal of the organic layer solvent, the residue was purified by column chromatography to obtain the target compound R45 (4.0 g, 7.1 mmol, yield 65%).
GC-Mass (이론치: 567.68 g/mol, 측정치: 567 g/mol)GC-Mass (calculated: 567.68 g / mol, measured: 567 g / mol)
[[ 합성예Synthetic example 29] 29] R46R46 의 합성Synthesis of
질소 기류 하에서 A5 7.5 g(11.0 mmol), 1,1-dimethyl-1H-inden-5-ylboronic acid 2.5 g(13.2 mmol), 0.6 g(5 mol%)의 Pd(PPh3)4 및 potassium carbonate 4.5 g(32.9 mmol)와 80 ml/40 ml/40 ml의 Toluene/H2O/Ethanol를 넣고 110℃에서 3시간 동안 교반하였다.In a nitrogen atmosphere A5 7.5 g (11.0 mmol), 1,1-dimethyl-1H-inden-5-ylboronic acid 2.5 g (13.2 mmol), 0.6 g (5 mol%) of Pd (PPh 3) 4, and potassium carbonate 4.5 g (32.9 mmol) and 80 ml / 40 ml / 40 ml of toluene / H 2 O / ethanol were added and stirred at 110 ° C for 3 hours.
반응 종료 후, 메틸렌클로라이드를 이용하여 유기층을 분리하고 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 R46(5.3 g, 7.1 mmol, 수율 70%)을 얻었다.After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO 4 . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the desired compound R46 (5.3 g, 7.1 mmol, yield 70%).
GC-Mass (이론치: 747.84 g/mol, 측정치: 747 g/mol)GC-Mass (747.84 g / mol, measured: 747 g / mol)
[[ 합성예Synthetic example 30] 30] R47R47 의 합성Synthesis of
질소 기류 하에서 A6 7.2 g(11.0 mmol), 1,1-dimethyl-1H-inden-5-ylboronic acid 2.5 g(13.2 mmol), 0.6 g(5 mol%)의 Pd(PPh3)4 및 potassium carbonate 4.5 g(32.9 mmol)와 80 ml/40 ml/40 ml의 Toluene/H2O/Ethanol를 넣고 110℃에서 3시간 동안 교반하였다.In a nitrogen atmosphere A6 7.2 g (11.0 mmol), 1,1-dimethyl-1H-inden-5-ylboronic acid 2.5 g (13.2 mmol), 0.6 g (5 mol%) of Pd (PPh 3) 4, and potassium carbonate 4.5 g (32.9 mmol) and 80 ml / 40 ml / 40 ml of toluene / H 2 O / ethanol were added and stirred at 110 ° C for 3 hours.
GC-Mass (이론치: 718.88 g/mol, 측정치: 718 g/mol)GC-Mass (calculated: 718.88 g / mol, measured: 718 g / mol)
[[ 합성예Synthetic example 31] 31] R51R51 의 합성Synthesis of
질소 기류 하에서 A7 6.6 g(11.3 mmol), 1H-indole 1.5 g(13.6 mmol), 0.5 g(5 mol%)의 Pd2(dba)3, tri-tert-butylphosphine 0.1 g(0.6 mmol) 및 Sodium tert-butoxide 3.3 g(33.9 mmol)와 100 ml의 Toluene을 넣고 110℃에서 4시간 동안 교반하였다.In a nitrogen atmosphere A7 6.6 g (11.3 mmol), 1H-indole 1.5 g (13.6 mmol), 0.5 g (5 mol%) of Pd 2 (dba) 3, tri- tert -butylphosphine 0.1 g (0.6 mmol) and Sodium tert -butoxide (3.3 g, 33.9 mmol) and 100 ml of toluene were placed, and the mixture was stirred at 110 DEG C for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R51 5.2 g(8.5 mmol, 수율 75%)을 얻었다.After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO 4 . The residue was purified by column chromatography to obtain 5.2 g (8.5 mmol, yield 75%) of the target compound R51.
GC-Mass (이론치: 616.71 g/mol, 측정치: 616 g/mol)GC-Mass (theory: 616.71 g / mol, measured: 616 g / mol)
[[ 합성예Synthetic example 32] 32] R53R53 의 합성Synthesis of
질소 기류 하에서 A8 7.1 g(11.3 mmol), 1H-indole 1.6 g(13.6 mmol), 0.5 g(5 mol%)의 Pd2(dba)3, tri-tert-butylphosphine 0.1 g(0.6 mmol) 및 Sodium tert-butoxide 3.3 g(33.9 mmol)와 100 ml의 Toluene을 넣고 110℃에서 4시간 동안 교반하였다.In a nitrogen atmosphere A8 7.1 g (11.3 mmol), 1H-indole 1.6 g (13.6 mmol), 0.5 g (5 mol%) of Pd 2 (dba) 3, tri- tert -butylphosphine 0.1 g (0.6 mmol) and Sodium tert -butoxide (3.3 g, 33.9 mmol) and 100 ml of toluene were placed, and the mixture was stirred at 110 DEG C for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R53 5.7 g(8.5 mmol, 수율 75%)을 얻었다.After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO 4 . The residue was purified by column chromatography to obtain 5.7 g (8.5 mmol, yield 75%) of the desired compound R53.
GC-Mass (이론치: 666.77 g/mol, 측정치: 666 g/mol)GC-Mass (calculated: 666.77 g / mol, measured: 666 g / mol)
[[ 합성예Synthetic example 33] 33] R54R54 의 합성Synthesis of
질소 기류 하에서 A9 6.6 g(11.3 mmol), 1H-indole 1.6 g(13.6 mmol), 0.5 g(5 mol%)의 Pd2(dba)3, tri-tert-butylphosphine 0.1 g(0.6 mmol) 및 Sodium tert-butoxide 3.3 g(33.9 mmol)와 100 ml의 Toluene을 넣고 110℃에서 4시간 동안 교반하였다.In a nitrogen atmosphere A9 6.6 g (11.3 mmol), 1H-indole 1.6 g (13.6 mmol), 0.5 g (5 mol%) of Pd 2 (dba) 3, tri- tert -butylphosphine 0.1 g (0.6 mmol) and Sodium tert -butoxide (3.3 g, 33.9 mmol) and 100 ml of toluene were placed, and the mixture was stirred at 110 DEG C for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R54 5.2 g(8.5 mmol, 수율 75%)을 얻었다.After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO 4 . The residue was purified by column chromatography to obtain 5.2 g (8.5 mmol, yield 75%) of the target compound R54.
GC-Mass (이론치: 617.70 g/mol, 측정치: 617 g/mol)GC-Mass (calculated: 617.70 g / mol, measured: 617 g / mol)
[[ 합성예Synthetic example 34] 34] R55R55 의 합성Synthesis of
질소 기류 하에서 A10 5.7 g(11.3 mmol), 1H-indole 1.6 g(13.6 mmol), 0.5 g(5 mol%)의 Pd2(dba)3, tri-tert-butylphosphine 0.1 g(0.6 mmol) 및 Sodium tert-butoxide 3.3 g(33.9 mmol)와 100 ml의 Toluene을 넣고 110℃에서 4시간 동안 교반하였다.A10 5.7 g (11.3 mmol), 1H-indole 1.6 g (13.6 mmol), 0.5 g (5 mol%) of Pd 2 (dba) 3, tri- tert -butylphosphine 0.1 g (0.6 mmol) and Sodium tert conducted in a nitrogen atmosphere -butoxide (3.3 g, 33.9 mmol) and 100 ml of toluene were placed, and the mixture was stirred at 110 DEG C for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R55 4.6 g(8.5 mmol, 수율 75%)을 얻었다.After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO 4 . The residue was purified by column chromatography to obtain 4.6 g (8.5 mmol, yield 75%) of the objective compound R55.
GC-Mass (이론치: 541.60 g/mol, 측정치: 541 g/mol)GC-Mass (calculated: 541.60 g / mol, measured: 541 g / mol)
[[ 합성예Synthetic example 35] 35] R56R56 의 합성Synthesis of
질소 기류 하에서 A11 7.8 g(11.3 mmol), 1H-indole 1.6 g(13.6 mmol), 0.5 g(5 mol%)의 Pd2(dba)3, tri-tert-butylphosphine 0.1 g(0.6 mmol) 및 Sodium tert-butoxide 3.3 g(33.9 mmol)와 100 ml의 Toluene을 넣고 110℃에서 4시간 동안 교반하였다.A11 7.8 g (11.3 mmol), 1H-indole 1.6 g (13.6 mmol), 0.5 g (5 mol%) of Pd 2 (dba) 3, tri- tert -butylphosphine 0.1 g (0.6 mmol) and Sodium tert conducted in a nitrogen atmosphere -butoxide (3.3 g, 33.9 mmol) and 100 ml of toluene were placed, and the mixture was stirred at 110 DEG C for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R56 6.1 g(8.5 mmol, 수율 75%)을 얻었다.After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO 4 . The residue was purified by column chromatography to obtain 6.1 g (8.5 mmol, yield 75%) of the target compound R56.
GC-Mass (이론치: 721.76 g/mol, 측정치: 721 g/mol)GC-Mass (calculated: 721.76 g / mol, measured: 721 g / mol)
[[ 합성예Synthetic example 36] 36] R57R57 의 합성Synthesis of
질소 기류 하에서 A12 7.4 g(11.3 mmol), 1H-indole 1.6 g(13.6 mmol), 0.5 g (5 mol%)의 Pd2(dba)3, tri-tert-butylphosphine 0.1 g(0.6 mmol) 및 Sodium tert-butoxide 3.3 g(33.9 mmol)와 100 ml의 Toluene을 넣고 110℃에서 4시간 동안 교반하였다.(11.3 mmol) of A12, 1.6 g (13.6 mmol) of 1H-indole, 0.5 g (5 mol%) of Pd 2 (dba) 3 , tri- tert- butylphosphine 0.1 g -butoxide (3.3 g, 33.9 mmol) and 100 ml of toluene were placed, and the mixture was stirred at 110 DEG C for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R57 5.9 g(8.5 mmol, 수율 75%)을 얻었다.After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO 4 . The residue was purified by column chromatography to obtain 5.9 g (8.5 mmol, yield 75%) of the target compound R57.
GC-Mass (이론치: 692.81 g/mol, 측정치: 692 g/mol)GC-Mass (calculated: 692.81 g / mol, measured: 692 g / mol)
[[ 합성예Synthetic example 37] 37] R61R61 의 합성Synthesis of
질소 기류 하에서 A7 6.6 g(11.3 mmol), 1H-indazole 1.6 g(13.6 mmol), 0.5 g(5 mol%)의 Pd2(dba)3, tri-tert-butylphosphine 0.1 g(0.6 mmol) 및 Sodium tert-butoxide 3.3 g(33.9 mmol)와 100 ml의 Toluene을 넣고 110℃에서 4시간 동안 교반하였다.In a nitrogen atmosphere A7 6.6 g (11.3 mmol), 1H-indazole 1.6 g (13.6 mmol), 0.5 g (5 mol%) of Pd 2 (dba) 3, tri- tert -butylphosphine 0.1 g (0.6 mmol) and Sodium tert -butoxide (3.3 g, 33.9 mmol) and 100 ml of toluene were placed, and the mixture was stirred at 110 DEG C for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R61 5.2 g(8.5 mmol, 수율 75%)을 얻었다.After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO 4 . The residue was purified by column chromatography to obtain 5.2 g (8.5 mmol, yield 75%) of the desired compound R61.
GC-Mass (이론치: 617.70 g/mol, 측정치: 617 g/mol)GC-Mass (calculated: 617.70 g / mol, measured: 617 g / mol)
[[ 합성예Synthetic example 38] 38] R71R71 의 합성Synthesis of
질소 기류 하에서 A7 6.6 g(11.3 mmol), 1H-benzo[d][1,2,3]triazole 1.6 g(13.6 mmol), 0.5 g(5 mol%)의 Pd2(dba)3, tri-tert-butylphosphine 0.1 g(0.6 mmol) 및 Sodium tert-butoxide 3.3 g(33.9 mmol)와 100 ml의 Toluene을 넣고 110℃에서 4시간 동안 교반하였다.In a nitrogen atmosphere A7 6.6 g (11.3 mmol), 1H-benzo [d] [1,2,3] triazole 1.6 g (13.6 mmol), 0.5 g (5 mol%) of Pd 2 (dba) 3, tri- tert -butylphosphine (0.1 g, 0.6 mmol), sodium tert-butoxide (3.3 g, 33.9 mmol) and 100 ml of toluene were placed and stirred at 110 ° C for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R71 5.2 g(8.5 mmol, 수율 75%)을 얻었다.After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO 4 . The residue was purified by column chromatography to obtain 5.2 g (8.5 mmol, yield 75%) of the desired compound R71.
GC-Mass (이론치: 618.69 g/mol, 측정치: 618 g/mol)GC-Mass (calculated: 618.69 g / mol, measured: 618 g / mol)
[[ 합성예Synthetic example 39] 39] R81R81 의 합성Synthesis of
질소 기류 하에서 A7 6.6 g(11.3 mmol), benzofuran-5-ylboronic acid 2.6 g(13.6 mmol), 0.6 g(5 mol%)의 Pd(PPh3)4 및 potassium carbonate 4.7 g(33.9 mmol)와 80 ml/40 ml/40 ml의 Toluene/H2O/Ethanol를 넣고 110℃에서 3시간 동안 교반하였다.A7 6.6 g (11.3 mmol), benzofuran-5-ylboronic acid 2.6 g (13.6 mmol), 0.6 g (5 mol%) of Pd (PPh 3) 4, and potassium carbonate 4.7 g (33.9 mmol) and 80 ml in a nitrogen atmosphere / 40 ml / 40 ml of Toluene / H 2 O / Ethanol was added, and the mixture was stirred at 110 ° C for 3 hours.
반응 종료 후, 메틸렌클로라이드를 이용하여 유기층을 분리하고 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 R81 4.5 g(7.3 mmol, 수율 70%)을 얻었다.After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO 4 . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain 4.5 g (7.3 mmol, yield 70%) of the target compound R81.
GC-Mass (이론치: 617.70 g/mol, 측정치: 617 g/mol)GC-Mass (calculated: 617.70 g / mol, measured: 617 g / mol)
[[ 합성예Synthetic example 40] 40] R91R91 의 합성Synthesis of
질소 기류 하에서 A7 6.6 g(11.3 mmol), 1,1-dimethyl-1H-inden-5-ylboronic acid 2.6 g(13.6 mmol), 0.6 g(5 mol%)의 Pd(PPh3)4 및 potassium carbonate 4.7 g(33.9 mmol)와 80 ml/40 ml/40 ml의 Toluene/H2O/Ethanol를 넣고 110℃에서 3시간 동안 교반하였다.In a nitrogen atmosphere A7 6.6 g (11.3 mmol), 1,1-dimethyl-1H-inden-5-ylboronic acid 2.6 g (13.6 mmol), 0.6 g (5 mol%) of Pd (PPh 3) 4, and potassium carbonate 4.7 g (33.9 mmol) and 80 ml / 40 ml / 40 ml of toluene / H 2 O / ethanol were added and stirred at 110 ° C for 3 hours.
반응 종료 후, 메틸렌클로라이드를 이용하여 유기층을 분리하고 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 R91 4.7 g(7.3 mmol, 수율 70%)을 얻었다.After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO 4 . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain 4.7 g (7.3 mmol, yield 70%) of the target compound R91.
GC-Mass (이론치: 643.78 g/mol, 측정치: 643 g/mol)GC-Mass (calculated: 643.78 g / mol, measured: 643 g / mol)
[[ 합성예Synthetic example 41] 41] R111R111 의 합성Synthesis of
질소 기류 하에서 A16 6.0 g(11.3 mmol), benzofuran-5-ylboronic acid 2.2 g(13.6 mmol), 0.6 g(5 mol%)의 Pd(PPh3)4 및 potassium carbonate 4.7 g(33.9 mmol)와 80 ml/40 ml/40 ml의 Toluene/H2O/Ethanol를 넣고 110℃에서 3시간 동안 교반하였다.A16 6.0 g (11.3 mmol), benzofuran-5-ylboronic acid 2.2 g (13.6 mmol), 0.6 g (5 mol%) of Pd (PPh 3) 4, and potassium carbonate 4.7 g (33.9 mmol) and 80 ml in a nitrogen atmosphere / 40 ml / 40 ml of Toluene / H 2 O / Ethanol was added, and the mixture was stirred at 110 ° C for 3 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R111 5.3 g(8.3 mmol, 수율 73%)을 얻었다.After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO 4 . The residue was purified by column chromatography to obtain 5.3 g (8.3 mmol, yield 73%) of the objective compound R111.
GC-Mass (이론치: 642.79 g/mol, 측정치: 642 g/mol)GC-Mass (calculated: 642.79 g / mol, measured: 642 g / mol)
[[ 합성예Synthetic example 42] 42] R113R113 의 합성Synthesis of
질소 기류 하에서 A14 7.4 g(11.3 mmol), benzofuran-5-ylboronic acid 2.2 g(13.6 mmol), 0.6 g(5 mol%)의 Pd(PPh3)4 및 potassium carbonate 4.7 g(33.9 mmol)와 80 ml/40 ml/40 ml의 Toluene/H2O/Ethanol를 넣고 110℃에서 3시간 동안 교반하였다.A14 7.4 g (11.3 mmol), benzofuran-5-ylboronic acid 2.2 g (13.6 mmol), 0.6 g (5 mol%) of Pd (PPh 3) 4, and potassium carbonate 4.7 g (33.9 mmol) and 80 ml in a nitrogen atmosphere / 40 ml / 40 ml of Toluene / H 2 O / Ethanol was added, and the mixture was stirred at 110 ° C for 3 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R113 5.7 g(8.3 mmol, 수율 73%)을 얻었다.After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO 4 . The residue was purified by column chromatography to obtain 5.7 g (8.3 mmol, yield 73%) of the target compound R113.
GC-Mass (이론치: 692.84 g/mol, 측정치: 692 g/mol)GC-Mass (calculated: 692.84 g / mol, measured: 692 g / mol)
[[ 합성예Synthetic example 43] 43] R114R114 의 합성Synthesis of
질소 기류 하에서 A15 6.9 g(11.3 mmol), benzofuran-5-ylboronic acid 2.2 g(13.6 mmol), 0.6 g(5 mol%)의 Pd(PPh3)4 및 potassium carbonate 4.7 g(33.9 mmol)와 80 ml/40 ml/40 ml의 Toluene/H2O/Ethanol를 넣고 110℃에서 3시간 동안 교반하였다.A15 6.9 g (11.3 mmol), benzofuran-5-ylboronic acid 2.2 g (13.6 mmol), 0.6 g (5 mol%) of Pd (PPh 3) 4, and potassium carbonate 4.7 g (33.9 mmol) and 80 ml in a nitrogen atmosphere / 40 ml / 40 ml of Toluene / H 2 O / Ethanol was added, and the mixture was stirred at 110 ° C for 3 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R114 5.3 g(8.3 mmol, 수율 73%)을 얻었다.After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO 4 . The residue was purified by column chromatography to obtain 5.3 g (8.3 mmol, yield 73%) of the target compound R114.
GC-Mass (이론치: 643.77 g/mol, 측정치: 643 g/mol)GC-Mass (calculated: 643.77 g / mol, measured: 643 g / mol)
[[ 합성예Synthetic example 44] 44] R115R115 의 합성Synthesis of
질소 기류 하에서 A16 6.0 g(11.3 mmol), benzofuran-5-ylboronic acid 2.2 g(13.6 mmol), 0.6 g(5 mol%)의 Pd(PPh3)4 및 potassium carbonate 4.7 g(33.9 mmol)와 80 ml/40 ml/40 ml의 Toluene/H2O/Ethanol를 넣고 110℃에서 3시간 동안 교반하였다.A16 6.0 g (11.3 mmol), benzofuran-5-ylboronic acid 2.2 g (13.6 mmol), 0.6 g (5 mol%) of Pd (PPh 3) 4, and potassium carbonate 4.7 g (33.9 mmol) and 80 ml in a nitrogen atmosphere / 40 ml / 40 ml of Toluene / H 2 O / Ethanol was added, and the mixture was stirred at 110 ° C for 3 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R115 4.7 g(8.3 mmol, 수율 73%)을 얻었다.After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO 4 . The residue was purified by column chromatography to obtain 4.7 g (8.3 mmol, yield 73%) of the desired compound R115.
GC-Mass (이론치: 567.68 g/mol, 측정치: 567 g/mol)GC-Mass (calculated: 567.68 g / mol, measured: 567 g / mol)
[[ 합성예Synthetic example 45] 45] R116R116 의 합성Synthesis of
질소 기류 하에서 A17 8.0 g(11.3 mmol), benzofuran-5-ylboronic acid 2.2 g(13.6 mmol), 0.6 g(5 mol%)의 Pd(PPh3)4 및 potassium carbonate 4.7 g(33.9 mmol)와 80 ml/40 ml/40 ml의 Toluene/H2O/Ethanol를 넣고 110℃에서 3시간 동안 교반하였다.A17 8.0 g (11.3 mmol), benzofuran-5-ylboronic acid 2.2 g (13.6 mmol), 0.6 g (5 mol%) of Pd (PPh 3) 4, and potassium carbonate 4.7 g (33.9 mmol) and 80 ml in a nitrogen atmosphere / 40 ml / 40 ml of Toluene / H 2 O / Ethanol was added, and the mixture was stirred at 110 ° C for 3 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R116 6.2 g(8.3 mmol, 수율 73%)을 얻었다.After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO 4 . The residue was purified by column chromatography to obtain 6.2 g (8.3 mmol, yield 73%) of the objective compound R116.
GC-Mass (이론치: 747.84 g/mol, 측정치: 747 g/mol)GC-Mass (747.84 g / mol, measured: 747 g / mol)
[[ 합성예Synthetic example 46] 46] R117R117 의 합성Synthesis of
질소 기류 하에서 A18 8.3 g(11.3 mmol), benzofuran-5-ylboronic acid 2.2 g(13.6 mmol), 0.6 g(5 mol%)의 Pd(PPh3)4 및 potassium carbonate 4.7 g(33.9 mmol)와 80 ml/40 ml/40 ml의 Toluene/H2O/Ethanol를 넣고 110℃에서 3시간 동안 교반하였다.A18 8.3 g (11.3 mmol), benzofuran-5-ylboronic acid 2.2 g (13.6 mmol), 0.6 g (5 mol%) of Pd (PPh 3) 4, and potassium carbonate 4.7 g (33.9 mmol) and 80 ml in a nitrogen atmosphere / 40 ml / 40 ml of Toluene / H 2 O / Ethanol was added, and the mixture was stirred at 110 ° C for 3 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R117 6.3 g(8.3 mmol, 수율 73%)을 얻었다.After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO 4 . The residue was purified by column chromatography to obtain 6.3 g (8.3 mmol, yield 73%) of the target compound R117.
GC-Mass (이론치: 766.92 g/mol, 측정치: 766 g/mol)GC-Mass (calculated: 766.92 g / mol, measured: 766 g / mol)
[[ 실시예Example 1 ~ 46] 녹색 유기 EL 소자의 제작 Fabrication of Green Organic EL Device
합성예에서 합성한 화합물들을 통상적으로 알려진 방법으로 고순도 승화정제를 한 후 아래의 과정에 따라 녹색 유기 EL 소자를 제작하였다.Compounds synthesized in Synthesis Examples were subjected to high purity sublimation purification by a conventionally known method, and green organic EL devices were fabricated according to the following procedure.
먼저, 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 5분간 세정하고 진공 증착기로 기판을 이송하였다.First, glass substrate coated with ITO (Indium tin oxide) thin film of 1500 Å thickness was cleaned 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, 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.
이렇게 준비된 ITO 투명 전극 위에 m-MTDATA (60 nm)/TCTA (80 nm)/ CBP + 10 % Ir(ppy)3 (300 nm)/BCP (10 nm)/Alq3 (30 nm)/LiF (1 nm)/Al (200 nm) 순으로 적층하여 유기 EL 소자를 제작하였다.(60 nm) / TCTA (80 nm) / CBP + 10% Ir (ppy) 3 (300 nm) / BCP (10 nm) / Alq 3 (30 nm) / LiF nm) / Al (200 nm) were stacked in this order to fabricate an organic EL device.
m-MTDATA, TCTA, Ir(ppy)3, CBP, Alq3 및 BCP의 구조는 하기와 같다.The structures of m-MTDATA, TCTA, Ir (ppy) 3 , CBP, Alq3 and BCP are as follows.
[[ 비교예Comparative Example 1] 녹색 유기 EL 소자의 제작 1] Fabrication of green organic EL device
전자 수송층 물질인 Alq3을 30 nm로 증착하는 것을 제외하고는, 실시예 1과 동일하게 수행하여 녹색 유기 전계 발광 소자를 제작하였다.A green organic electroluminescent device was fabricated in the same manner as in Example 1, except that Alq 3 , an electron transporting material, was deposited at 30 nm.
[[ 평가예1Evaluation example 1 ]]
실시예 1 ~ 46 및 비교예 1에서 제작한 각각의 녹색 유기 EL 소자에 대하여 전류밀도 (10) mA/㎠에서의 구동전압, 전류효율 및 발광 피크를 측정하고, 그 결과를 하기 표 1에 나타내었다.The driving voltage, current efficiency and emission peak at the current density (10) mA / cm 2 were measured for each of the green organic EL devices manufactured in Examples 1 to 46 and Comparative Example 1, and the results are shown in the following Table 1 .
(V)Driving voltage
(V)
(nm)Emission peak
(nm)
(cd/A)Current efficiency
(cd / A)
상기 표 1에 나타낸 바와 같이, 본 발명에 따른 화합물(실시예 1-46)을 녹색 유기 EL 소자의 발광층으로 사용하였을 경우 종래 Alq3를 전자수송층으로 사용한 녹색 유기 EL 소자(비교예1)와 비교해 볼 때 효율 및 구동전압 면에서 보다 우수한 성능을 나타내는 것을 알 수 있다.As shown in Table 1, when the compound according to the present invention (Example 1-46) was used as a light emitting layer of a green organic EL device, compared with a green organic EL device (Comparative Example 1) using Alq3 as an electron transport layer in the prior art It can be seen that it exhibits better performance in terms of efficiency and driving voltage.
Claims (9)
[화학식 1]
상기 화학식 1에서,
X1 내지 X6 은 각각 서로 동일하거나 상이하며, C, N 중 하나의 원자를 함유하고,
A와 B는 각각 서로 동일하거나 상이하며, 독립적으로 하기 화학식 2 또는 화학식 3으로 표시될 수 있고
[화학식 2]
[화학식 3]
상기 화학식 2 또는 화학식 3에서,
X7 내지 X9 은 각각 서로 동일하거나 상이하며, S, O, N(Ar1), C(Ar2)(Ar3) 중 어느 하나의 원자를 함유하고,
n은 0 내지 4의 정수이며,
C는 하기 화학식 4 로 표현되는 치환기이고,
[화학식 4]
상기 화학식 4에서,
*은 X1 내지 X6 와 결합이 이루어지는 부분을 의미하고;
L1은 단일결합, C6~C18의 아릴렌기 및 핵원자수 5 내지 18개의 헤테로아릴렌기로 이루어진 군에서 선택되며;
R1 내지 R3와 Ar1 내지 Ar3은 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성하며;
상기 L1의 아릴렌기 및 헤테로아릴렌기와, 상기 R1 및 R2 와 Ar1 내지 Ar3 의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다.A compound represented by the following formula (1):
[Chemical Formula 1]
In Formula 1,
X 1 to X 6 are the same or different from each other and contain one atom of C and N,
A and B are the same or different from each other and independently can be represented by the following formula (2) or (3)
(2)
(3)
In Formula 2 or Formula 3,
X 7 to X 9 are the same or different from each other and contain any one of S, O, N (Ar 1 ) and C (Ar 2 ) (Ar 3 )
n is an integer of 0 to 4,
C is a substituent represented by the following formula (4)
[Chemical Formula 4]
In Formula 4,
* Represents a moiety in which X 1 to X 6 are bonded;
L 1 is selected from the group consisting of a single bond, a C 6 to C 18 arylene group and a heteroarylene group having 5 to 18 nuclear atoms;
R 1 to R 3 and Ar 1 to Ar 3 are each independently selected from hydrogen, deuterium, halogen, cyano, nitro, C 1 to C 40 alkyl, C 2 to C 40 alkenyl, C 2 to C 40 alkynyl, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 6 ~ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 1 ~ alkyloxy group of C 40, A C 6 to C 60 aryloxy group, a C 3 to C 40 alkylsilyl group, a C 6 to C 60 arylsilyl group, a C 1 to C 40 alkylboron group, a C 6 to C 60 arylboron group, C 6 ~ C 60 aryl phosphazene group, C 6 ~ C 60 mono or diaryl phosphine blood group and a C 6 ~, or selected from the group consisting of an aryl amine of the C 60, the combined group adjacent to form a condensed ring ;
An alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group or a heterocyclic group of the above-mentioned L 1 and an arylene group and a heteroarylene group of R 1 and R 2 and Ar 1 to Ar 3 , A heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkylboron group, an arylboron group, an arylphosphonyl group, a mono- or diarylphosphinyl group, and an arylsilyl group are each independently selected from deuterium, halogen, cyano, nitro, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, an alkynyl group of C 2 ~ C 40, C 6 ~ aryl group of C 60, nuclear atoms of 5 to 60 heteroaryl group, C 6 ~ C aryloxy 60, C 1 ~ C 40 alkyloxy group of, C 6 ~ C 60 aryl amine group, C 3 ~ cycloalkyl group of C 40, nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkylsilyl group, C 1 ~ C 40 alkyl group of boron, C 6 ~ C 60 aryl group of boron, C 6 ~ C 60 aryl phosphazene group, C 6 ~ C 60 of the mono or diaryl phosphine If group and a C 6 ~ C substituted with one or more substituents selected from the 60 group consisting of aryl silyl or is unsubstituted, substituted by a plurality of substituents, they may be the same or different from each other.
상기 화학식 1의 화합물은 하기 화학식 5로 표시되는 것인 화합물:
[화학식 5]
상기 화학식 5에서,
X7 내지 X9, n, R1 내지 R3 및 L1 각각은 상기 화학식 1 내지 상기 화학식 3에서 정의된 바와 같다.The method according to claim 1,
Wherein the compound of Formula 1 is represented by Formula 5:
[Chemical Formula 5]
In Formula 5,
X 7 to X 9 , n, R 1 To R 3 and L 1 each are as defined in Formula 1 to Formula 3.
상기 A는 하기 구조에서 선택되는 것인 화합물:
, , , ,
, , ,
, , .The method according to claim 1,
Wherein A is selected from the following structures:
, , , ,
, , ,
, , .
상기 B는 하기 구조에서 선택되는 것인 화합물:
, , , ,
, , ,
, , , ,
, , ,
, , ,
, , ,
.The method according to claim 1,
Wherein B is selected from the following structures:
, , , ,
, , ,
, , , ,
, , ,
, , ,
, , ,
.
상기 L1은 피리미딘 또는 트리아진인 화합물.The method according to claim 1,
Wherein L < 1 > is pyrimidine or triazine.
상기 R2와 R3는 서로 동일하거나 상이하며, 하기 구조에서 선택되는 것인 화합물:
, , , .The method according to claim 1,
Wherein R 2 and R 3 are the same or different and are selected from the following structures:
, , , .
상기 C는 하기 구조에서 선택되는 것인 화합물:
, ,
, .The method according to claim 1,
Wherein C is selected from the following structures:
, ,
, .
상기 1층 이상의 유기물층 중에서 적어도 하나는 제1항 내지 제7항 중 어느 한 항에 기재된 화합물을 포함하는 유기 전계 발광 소자.1. An organic electroluminescent device comprising an anode, a 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 the compound according to any one of claims 1 to 7.
상기 1층 이상의 유기물층은 정공주입층, 정공수송층, 발광층, 전자수송층 및 전자주입층을 포함하고,
상기 화합물을 포함하는 1층 이상의 유기물층은 전자수송층 또는 전자주입층인 유기 전계 발광 소자.9. The method of claim 8,
Wherein the one or more organic layers include a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer,
Wherein at least one organic compound layer containing the compound is an electron transporting layer or an electron injecting layer.
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