JPWO2010104047A1 - Polycyclic aromatic compounds - Google Patents
Polycyclic aromatic compounds Download PDFInfo
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- JPWO2010104047A1 JPWO2010104047A1 JP2011503815A JP2011503815A JPWO2010104047A1 JP WO2010104047 A1 JPWO2010104047 A1 JP WO2010104047A1 JP 2011503815 A JP2011503815 A JP 2011503815A JP 2011503815 A JP2011503815 A JP 2011503815A JP WO2010104047 A1 JPWO2010104047 A1 JP WO2010104047A1
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- Prior art keywords
- group
- substituted
- aryl
- alkyl
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- -1 Polycyclic aromatic compounds Chemical class 0.000 title claims description 170
- 150000001875 compounds Chemical class 0.000 claims abstract description 147
- 125000003118 aryl group Chemical group 0.000 claims description 39
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- 125000004432 carbon atom Chemical group C* 0.000 claims description 25
- 125000001072 heteroaryl group Chemical group 0.000 claims description 24
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 23
- 229910052799 carbon Inorganic materials 0.000 claims description 22
- 125000005842 heteroatom Chemical group 0.000 claims description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
- 125000004122 cyclic group Chemical group 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 18
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 12
- 125000003277 amino group Chemical group 0.000 claims description 12
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 10
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 10
- 125000004986 diarylamino group Chemical group 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 9
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 9
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 9
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 7
- 150000002367 halogens Chemical group 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 229910052698 phosphorus Inorganic materials 0.000 claims description 7
- 125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 7
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 7
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000006624 (C1-C6) alkoxycarbonylamino group Chemical group 0.000 claims description 6
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 229910052785 arsenic Inorganic materials 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 5
- 125000006597 (C1-C3) alkylcarbonylamino group Chemical group 0.000 claims description 4
- 125000006602 (C1-C3) alkylsulfonylamino group Chemical group 0.000 claims description 4
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- 229960002324 trifluoperazine Drugs 0.000 claims description 2
- 239000002904 solvent Substances 0.000 description 79
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 45
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 40
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- 239000000243 solution Substances 0.000 description 27
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 23
- 239000000843 powder Substances 0.000 description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 239000012300 argon atmosphere Substances 0.000 description 21
- 239000000460 chlorine Substances 0.000 description 21
- 239000010410 layer Substances 0.000 description 20
- 239000000203 mixture Substances 0.000 description 20
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 18
- 239000012043 crude product Substances 0.000 description 13
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 12
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 12
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 12
- 229910052717 sulfur Inorganic materials 0.000 description 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 10
- 239000011133 lead Substances 0.000 description 10
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 10
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 10
- 229920005989 resin Polymers 0.000 description 10
- 239000011347 resin Substances 0.000 description 10
- 239000011593 sulfur Substances 0.000 description 10
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 239000000654 additive Substances 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
- 230000000996 additive effect Effects 0.000 description 7
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 7
- 125000005605 benzo group Chemical group 0.000 description 7
- 238000009835 boiling Methods 0.000 description 7
- 239000010408 film Substances 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- 229910052763 palladium Inorganic materials 0.000 description 7
- 238000010898 silica gel chromatography Methods 0.000 description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
- 239000008096 xylene Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 229910052740 iodine Inorganic materials 0.000 description 6
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 6
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 6
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 6
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 150000002894 organic compounds Chemical class 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- 239000011135 tin Substances 0.000 description 6
- FTTATHOUSOIFOQ-UHFFFAOYSA-N 1,2,3,4,6,7,8,8a-octahydropyrrolo[1,2-a]pyrazine Chemical compound C1NCCN2CCCC21 FTTATHOUSOIFOQ-UHFFFAOYSA-N 0.000 description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
- KOEQOFXQZODDRY-UHFFFAOYSA-N IC1=C(C=CC=C1C1=C(C=CC2=CC=CC=C12)C)C1=C(C=CC2=CC=CC=C12)C Chemical compound IC1=C(C=CC=C1C1=C(C=CC2=CC=CC=C12)C)C1=C(C=CC2=CC=CC=C12)C KOEQOFXQZODDRY-UHFFFAOYSA-N 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 229940117389 dichlorobenzene Drugs 0.000 description 4
- 239000011630 iodine Substances 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 4
- 235000019345 sodium thiosulphate Nutrition 0.000 description 4
- 238000001665 trituration Methods 0.000 description 4
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 4
- CXNIUSPIQKWYAI-UHFFFAOYSA-N xantphos Chemical compound C=12OC3=C(P(C=4C=CC=CC=4)C=4C=CC=CC=4)C=CC=C3C(C)(C)C2=CC=CC=1P(C=1C=CC=CC=1)C1=CC=CC=C1 CXNIUSPIQKWYAI-UHFFFAOYSA-N 0.000 description 4
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 3
- FRKJGFAPMOHVAM-UHFFFAOYSA-M [Br-].C1=CC=CC2=C([Mg+])C(C)=CC=C21 Chemical compound [Br-].C1=CC=CC2=C([Mg+])C(C)=CC=C21 FRKJGFAPMOHVAM-UHFFFAOYSA-M 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 229910052796 boron Inorganic materials 0.000 description 3
- 125000001246 bromo group Chemical group Br* 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 125000002541 furyl group Chemical group 0.000 description 3
- 229910052733 gallium Inorganic materials 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- JVEHJSIFWIIFHM-UHFFFAOYSA-N n-[chloro(diethylamino)phosphanyl]-n-ethylethanamine Chemical compound CCN(CC)P(Cl)N(CC)CC JVEHJSIFWIIFHM-UHFFFAOYSA-N 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 3
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 3
- 125000003367 polycyclic group Chemical group 0.000 description 3
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 3
- 125000001544 thienyl group Chemical group 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 2
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- ZMPGXSFTXBOKFM-UHFFFAOYSA-N 1,3-dichloro-2-iodobenzene Chemical compound ClC1=CC=CC(Cl)=C1I ZMPGXSFTXBOKFM-UHFFFAOYSA-N 0.000 description 2
- ZPQOPVIELGIULI-UHFFFAOYSA-N 1,3-dichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1 ZPQOPVIELGIULI-UHFFFAOYSA-N 0.000 description 2
- HCVBSJHCKFEGDF-UHFFFAOYSA-N 1-[2,5-diiodo-3,4,6-tris(2-methylnaphthalen-1-yl)phenyl]-2-methylnaphthalene Chemical compound IC=1C(=C(C(=C(C1C1=C(C=CC2=CC=CC=C12)C)C1=C(C=CC2=CC=CC=C12)C)I)C1=C(C=CC2=CC=CC=C12)C)C1=C(C=CC2=CC=CC=C12)C HCVBSJHCKFEGDF-UHFFFAOYSA-N 0.000 description 2
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 2
- 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 2
- 125000006017 1-propenyl group Chemical group 0.000 description 2
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 2
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 2
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 2
- 125000006029 2-methyl-2-butenyl group Chemical group 0.000 description 2
- 125000006022 2-methyl-2-propenyl group Chemical group 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 2
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 2
- 125000006032 3-methyl-3-butenyl group Chemical group 0.000 description 2
- 125000006043 5-hexenyl group Chemical group 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- PHUBXYTWYONRNM-UHFFFAOYSA-N C1=CC=C2C(=C1)C=C3C=CC=CC3=C2N(C4=C5C=CC=CC5=CC6=CC=CC=C64)C7=C(C=CC=C7Cl)Cl Chemical compound C1=CC=C2C(=C1)C=C3C=CC=CC3=C2N(C4=C5C=CC=CC5=CC6=CC=CC=C64)C7=C(C=CC=C7Cl)Cl PHUBXYTWYONRNM-UHFFFAOYSA-N 0.000 description 2
- ZYHJJHDJWLHCTG-UHFFFAOYSA-N C1=CC=C2C(P(N(CC)CC)N(CC)CC)=C(C)C=CC2=C1 Chemical compound C1=CC=C2C(P(N(CC)CC)N(CC)CC)=C(C)C=CC2=C1 ZYHJJHDJWLHCTG-UHFFFAOYSA-N 0.000 description 2
- GZDCJHQBSBNKKB-UHFFFAOYSA-N CC1=C(C2=CC=CC=C2C=C1)P(N(CC)CC)(N(CC)CC)=S Chemical compound CC1=C(C2=CC=CC=C2C=C1)P(N(CC)CC)(N(CC)CC)=S GZDCJHQBSBNKKB-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 101150003085 Pdcl gene Proteins 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
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- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000005929 isobutyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC(*)=O 0.000 description 1
- 125000005932 isopentyloxycarbonyl group Chemical group 0.000 description 1
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000000113 methacrylic resin Substances 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000005184 naphthylamino group Chemical group C1(=CC=CC2=CC=CC=C12)N* 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 125000004998 naphthylethyl group Chemical group C1(=CC=CC2=CC=CC=C12)CC* 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000004675 pentylcarbonyl group Chemical group C(CCCC)C(=O)* 0.000 description 1
- 125000001148 pentyloxycarbonyl group Chemical group 0.000 description 1
- XDJOIMJURHQYDW-UHFFFAOYSA-N phenalene Chemical compound C1=CC(CC=C2)=C3C2=CC=CC3=C1 XDJOIMJURHQYDW-UHFFFAOYSA-N 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000005302 thiazolylmethyl group Chemical group [H]C1=C([H])N=C(S1)C([H])([H])* 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 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 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- CTJCBHGPXMQMJV-UHFFFAOYSA-N triiodomethylsilane Chemical compound [SiH3]C(I)(I)I CTJCBHGPXMQMJV-UHFFFAOYSA-N 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
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
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- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/48—Phosphonous acids [RP(OH)2] including [RHP(=O)(OH)]; Thiophosphonous acids including [RP(SH)2], [RHP(=S)(SH)]; Derivatives thereof
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- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
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- C07F9/50—Organo-phosphines
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Abstract
下記一般式(I)で表される化合物。【化1】(式中、X、X1、X2、X3、Z1、Z2は、明細書に定義されるとおりである。)The compound represented by the following general formula (I). Wherein X, X1, X2, X3, Z1, and Z2 are as defined in the specification.
Description
本発明は、新規化合物に関し、詳しくは、ヘテロ原子を含み得る多環芳香族化合物及び有機発光素子に関する。 The present invention relates to a novel compound, and more particularly to a polycyclic aromatic compound and an organic light emitting device that may contain a hetero atom.
従来、有機ELデバイスに用いる発光材料としてα-NPD、rubrene、Alq3、PBDなどが研究されてきた(特許文献1〜3)。 Conventionally, α-NPD, rubrene, Alq3, PBD, and the like have been studied as light emitting materials used in organic EL devices (Patent Documents 1 to 3).
有機発光素子は、陽極と陰極間に蛍光性有機化合物または燐光性有機化合物を含む薄膜を挟持させている。各電極から電子およびホール(正孔)を注入することにより、蛍光性化合物または燐光性化合物の励起子を生成させ、この励起子が基底状態にもどる際に放射される光を利用する素子である。 In the organic light emitting device, a thin film containing a fluorescent organic compound or a phosphorescent organic compound is sandwiched between an anode and a cathode. It is an element that uses light emitted when excitons of fluorescent compounds or phosphorescent compounds are generated by injecting electrons and holes (holes) from each electrode, and these excitons return to the ground state. .
また有機発光素子における最近の進歩は著しく、その特徴は低印加電圧で高輝度、発光波長の多様性、高速応答性、薄型、軽量の発光デバイス化が可能であることから、広汎な用途への可能性を示唆している。 Recent advances in organic light-emitting devices are remarkable, and their features are high brightness, diversity of emission wavelengths, high-speed response, thin and light-weight light-emitting devices with low applied voltage, and they can be used in a wide range of applications. Suggests the possibility.
しかしながら、現状では更なる高輝度の光出力あるいは高変換効率が必要である。また、長時間の使用による経時変化や酸素を含む雰囲気気体や湿気などによる劣化等の耐久性の面で未だ多くの問題がある。さらにはフルカラーディスプレイ等への応用を考えた場合の色純度の良い青、緑、赤の発光が必要となるが、これらの問題に関してもまだ十分でない。 However, under the present circumstances, light output with higher brightness or higher conversion efficiency is required. In addition, there are still many problems in terms of durability, such as changes over time due to long-term use and deterioration due to atmospheric gas containing oxygen or moisture. Furthermore, it is necessary to emit blue, green, and red light with good color purity when considering application to a full color display or the like, but these problems are still not sufficient.
また、中心にヘテロ原子を有し得る多環芳香族化合物の開示はない。 There is no disclosure of a polycyclic aromatic compound that may have a hetero atom at the center.
本発明の目的は、ヘテロ原子または炭素原子を中心に持つことができる新規多環芳香族化合物及び有機発光素子を提供することにある。 An object of the present invention is to provide a novel polycyclic aromatic compound and an organic light emitting device that can have a hetero atom or a carbon atom as a center.
本発明者は、以下の中心元素(X)により構造が固定された新規な多環芳香族化合物及び該化合物を含む有機発光素子を提供するものである。
項1. 下記一般式(I)で表される化合物。The present inventor provides a novel polycyclic aromatic compound having a structure fixed by the following central element (X) and an organic light-emitting device containing the compound.
Item 1. The compound represented by the following general formula (I).
(式中、X、X1、X2、X3、Z1、Z2は、以下の(i)〜(iii)のいずれかである:
(i) Z1、X、Z2が、それらが結合している炭素原子と一緒になって以下の式(A1)、(A2)または(A3)の構造を示す場合、X2、X1、X3は同一又は異なってR1を示すか、それらが結合している炭素原子と一緒になって各々Y7、Y8、Y9を示す。Y1〜Y15は同一または異なって、NまたはCR1を示す。Xはヘテロ原子もしくはその誘導体またはCR1を示す。(Wherein, X, X 1 , X 2 , X 3 , Z 1 , Z 2 are any of the following (i) to (iii):
(i) when Z 1 , X, Z 2 together with the carbon atom to which they are attached show the structure of the following formula (A1), (A2) or (A3), X 2 , X 1 , X 3 are the same or different and each represents R 1 , or together with the carbon atom to which they are bonded, each represents Y 7 , Y 8 , Y 9 . Y 1 to Y 15 are the same or different and represent N or CR 1 . X represents a hetero atom or a derivative thereof or CR 1 .
(ii) Z1、X、Z2が、それらが結合している炭素原子と一緒になって上記の式(A1)の構造を示し、X1、X2、X3が、それらが結合している炭素原子と一緒になって下記の式(A3)の構造を示す。式(A3)中、Y1〜Y6、Y10〜Y15、Y1’〜Y6’、Y10’〜Y15’は同一または異なって、NまたはCR1を示す。X1はヘテロ原子もしくはその誘導体またはCR1を示す。(ii) Z 1 , X, Z 2 together with the carbon atom to which they are attached show the structure of formula (A1) above, and X 1 , X 2 , X 3 are attached to Together with the carbon atom, the structure of the following formula (A3) is shown. In formula (A3), Y 1 to Y 6 , Y 10 to Y 15 , Y 1 ′ to Y 6 ′ , Y 10 ′ to Y 15 ′ are the same or different and represent N or CR 1 . X 1 represents a heteroatom or a derivative thereof or CR 1 .
(iii) X、X1、X2、X3、Z1、Z2が、それらが結合している炭素原子と一緒になって下記の式(A5)の構造を示す。式(A5)中、Y1〜Y15、Y1’〜Y15’、Y1’’〜Y21’’は同一または異なって、NまたはCR1を示す。X、X2、X3は、同一又は異なってヘテロ原子もしくはその誘導体またはCR1を示す。(iii) X, X 1 , X 2 , X 3 , Z 1 , Z 2 together with the carbon atom to which they are attached show the structure of formula (A5) below. In formula (A5), Y 1 to Y 15 , Y 1 ′ to Y 15 ′ , Y 1 ″ to Y 21 ″ are the same or different and represent N or CR 1 . X, X 2 and X 3 are the same or different and each represents a hetero atom or a derivative thereof or CR 1 .
R1は水素原子、ハロゲン原子、C1−6アルコキシ基、アリールオキシ基、トリフルオロメチル基、ヒドロキシ基、C1−6アルキル基、C3−7シクロアルキル基、C3−7シクロアルキル置換C1−4アルキル基、C2−6アルケニル基、C2−6アルキニル基、C1−6アルコキシ基、トリフルオロメトキシ基、トリフルオロエトキシ基、C1−10アルキルカルボニル基、C1−2アルキルスルホニル基、シアノ基、ニトロ基、アミノ基、モノ若しくはジ置換アミノ基、モノアリールアミノ基、ジアリールアミノ基、カルバゾール基、C1−6アルコキシカルボニルアミノ基、カルバモイル基、モノ若しくはジ置換カルバモイル基、スルファモイル基、モノ若しくはジ置換スルファモイル基、C1−6アルキルスルホニルアミノ基、アリール基、ヘテロアリール基、C1−6アルコキシカルボニル基、アリール置換C1−4アルコキシカルボニル基、カルボキシル基、5−テトラゾリル基、スルホ基(−SO2OH)又はフルオロスルホニル基を意味し、ただし、アルキル基、アルケニル基及びアルキニル基は、ハロゲン、ヒドロキシ、ジ置換アミノ、アリール置換C1−4アルキル基、ヘテロアリール置換C1−4アルキル基、アリール及びヘテロアリールから選択される1〜3個の原子又は基で置換されていてもよく、かつ、上記アリール基、アリール部分、ヘテロアリール基、ヘテロアリール部分は、ハロゲン、ヒドロキシ、C1−6アルキル、ヒドロキシC1−3アルキル、C1−6アルコキシ、トリフルオロメチル、トリフルオロメトキシ、トリフルオロエトキシ、シアノ、ニトロ、アミノ、モノ若しくはジ置換アミノ、カルバモイル、スルファモイル、C1−6アルキルスルホニル、C1−3アルキルスルホニルアミノ、C1−3アルキルカルボニルアミノ、メチレンジオキシ、モノアリールアミノ、ジアリールアミノ、カルバゾール、ヘテロアリール及びアリール(当該アリールは、ハロゲン原子、C1−6アルコキシ基、トリフルオロメチル基、ヒドロキシ基、C1−6アルキル基、C3−7シクロアルキル基、C3−7シクロアルキル置換C1−4アルキル基、C2−6アルケニル基、C2−6アルキニル基、C1−6アルコキシ基、トリフルオロメトキシ基、トリフルオロエトキシ基、C1−10アルキルカルボニル基、C1−2アルキルスルホニル基、シアノ基、ニトロ基またはアミノ基でモノ置換もしくはジ置換されていてもよい)から選択される1〜4個の原子又は基で置換されていてもよい。或いは、隣接するY1〜Y15、Y1’〜Y6’、Y10’〜Y15’、Y1’’〜Y21’’のいずれかに結合している隣接する2つのR1基は、これらが結合している炭素原子と一緒になって5員環又は6員環のヘテロ原子を有していてもよい環式基を示し、Y1〜Y15、Y1’〜Y6’、Y10’〜Y15’、Y1’’〜Y21’’のいずれかに結合している隣接する3つのR1基は、これらが結合している炭素原子と一緒になって2環または3環の芳香族環式基を示す。))
項2. 下記一般式(IA1)、(IA2)、(IA3)、(IA4)または(IA5)で表される、項1に記載の化合物。R 1 is a hydrogen atom, a halogen atom, a C 1-6 alkoxy group, an aryloxy group, a trifluoromethyl group, a hydroxy group, a C 1-6 alkyl group, a C 3-7 cycloalkyl group, or a C 3-7 cycloalkyl substitution. C 1-4 alkyl group, C 2-6 alkenyl group, C 2-6 alkynyl group, C 1-6 alkoxy group, trifluoromethoxy group, trifluoroethoxy group, C 1-10 alkylcarbonyl group, C 1-2 Alkylsulfonyl group, cyano group, nitro group, amino group, mono- or di-substituted amino group, monoarylamino group, diarylamino group, carbazole group, C 1-6 alkoxycarbonylamino group, carbamoyl group, mono- or di-substituted carbamoyl group , Sulfamoyl group, mono- or di-substituted sulfamoyl group, C 1-6 alkylsulfonyl Amino group, aryl group, heteroaryl group, C 1-6 alkoxycarbonyl group, aryl-substituted C 1-4 alkoxycarbonyl group, carboxyl group, 5-tetrazolyl group, sulfo group (—SO 2 OH) or fluorosulfonyl group Provided that the alkyl group, alkenyl group and alkynyl group are selected from halogen, hydroxy, di-substituted amino, aryl-substituted C 1-4 alkyl group, heteroaryl-substituted C 1-4 alkyl group, aryl and heteroaryl. May be substituted with ˜3 atoms or groups, and the aryl group, aryl moiety, heteroaryl group, heteroaryl moiety may be halogen, hydroxy, C 1-6 alkyl, hydroxy C 1-3 alkyl, C 1-6 alkoxy, trifluoromethyl, trifluoromethoxy, Ruoroetokishi, cyano, nitro, amino, mono- or di-substituted amino, carbamoyl, sulfamoyl, C 1-6 alkylsulfonyl, C 1-3 alkylsulfonylamino, C 1-3 alkylcarbonylamino, methylenedioxy, monoarylamino, diaryl Amino, carbazole, heteroaryl and aryl (the aryl is a halogen atom, a C 1-6 alkoxy group, a trifluoromethyl group, a hydroxy group, a C 1-6 alkyl group, a C 3-7 cycloalkyl group, a C 3-7 Cycloalkyl-substituted C 1-4 alkyl group, C 2-6 alkenyl group, C 2-6 alkynyl group, C 1-6 alkoxy group, trifluoromethoxy group, trifluoroethoxy group, C 1-10 alkylcarbonyl group, C 1-2 alkylsulfonyl group, a cyano group, two May be substituted with 1-4 atoms or groups selected from B may be mono- or di-substituted with a group or an amino group). Alternatively, two adjacent R 1 groups bonded to any one of adjacent Y 1 to Y 15 , Y 1 ′ to Y 6 ′ , Y 10 ′ to Y 15 ′ , and Y 1 ″ to Y 21 ″. It is that they show a cyclic group which may have a hetero atom a 5- or 6-membered ring together with the carbon atom bonded, Y 1 ~Y 15, Y 1 '~Y 6 Three adjacent R 1 groups bonded to any one of ' , Y 10 ′ to Y 15 ′ , Y 1 ″ to Y 21 ″ together with the carbon atom to which they are bonded are 2 A ring or a tricyclic aromatic cyclic group is shown. ))
Item 2. Item 6. The compound according to item 1, represented by the following general formula (IA1), (IA2), (IA3), (IA4) or (IA5).
(式中、Y1〜Y15、Y1’〜Y6’、Y10’〜Y15’、Y1’’〜Y21’’は同一または異なって、NまたはCR1を示す。R1は、水素原子、ハロゲン原子、C1−6アルコキシ基、アリールオキシ基、トリフルオロメチル基、ヒドロキシ基、C1−6アルキル基、C3−7シクロアルキル基、C3−7シクロアルキル置換C1−4アルキル基、C2−6アルケニル基、C2−6アルキニル基、C1−6アルコキシ基、トリフルオロメトキシ基、トリフルオロエトキシ基、C1−10アルキルカルボニル基、C1−2アルキルスルホニル基、シアノ基、ニトロ基、アミノ基、モノ若しくはジ置換アミノ基、モノアリールアミノ基、ジアリールアミノ基、カルバゾール基、C1−6アルコキシカルボニルアミノ基、カルバモイル基、モノ若しくはジ置換カルバモイル基、スルファモイル基、モノ若しくはジ置換スルファモイル基、C1−6アルキルスルホニルアミノ基、アリール基、ヘテロアリール基、C1−6アルコキシカルボニル基、アリール置換C1−4アルコキシカルボニル基、カルボキシル基、5−テトラゾリル基、スルホ基(−SO2OH)又はフルオロスルホニル基を意味し、ただし、アルキル基、アルケニル基及びアルキニル基は、ハロゲン、ヒドロキシ、ジ置換アミノ、アリール置換C1−4アルキル基、ヘテロアリール置換C1−4アルキル基、アリール及びヘテロアリールから選択される1〜3個の原子又は基で置換されていてもよく、かつ、上記アリール基、アリール部分、ヘテロアリール基、ヘテロアリール部分は、ハロゲン、ヒドロキシ、C1−6アルキル、ヒドロキシC1−3アルキル、C1−6アルコキシ、トリフルオロメチル、トリフルオロメトキシ、トリフルオロエトキシ、シアノ、ニトロ、アミノ、モノ若しくはジ置換アミノ、カルバモイル、スルファモイル、C1−6アルキルスルホニル、C1−3アルキルスルホニルアミノ、C1−3アルキルカルボニルアミノ、メチレンジオキシ、モノアリールアミノ、ジアリールアミノ、カルバゾール、ヘテロアリール及びアリール(当該アリールは、ハロゲン原子、C1−6アルコキシ基、トリフルオロメチル基、ヒドロキシ基、C1−6アルキル基、C3−7シクロアルキル基、C3−7シクロアルキル置換C1−4アルキル基、C2−6アルケニル基、C2−6アルキニル基、C1−6アルコキシ基、トリフルオロメトキシ基、トリフルオロエトキシ基、C1−10アルキルカルボニル基、C1−2アルキルスルホニル基、シアノ基、ニトロ基またはアミノ基でモノ置換もしくはジ置換されていてもよい)から選択される1〜4個の原子又は基で置換されていてもよい。或いは、隣接するY1〜Y15、Y1’〜Y6’、Y10’〜Y15’、Y1’’〜Y21’’のいずれかに結合している隣接する2つのR1基は、これらが結合している炭素原子と一緒になって5員環又は6員環のヘテロ原子を有していてもよい環式基を示し、Y1〜Y15、Y1’〜Y6’、Y10’〜Y15’、Y1’’〜Y21’’のいずれかに結合している隣接する3つのR1基は、これらが結合している炭素原子と一緒になって2環または3環の芳香族環式基を示す。Wherein Y 1 to Y 15 , Y 1 ′ to Y 6 ′ , Y 10 ′ to Y 15 ′ , Y 1 ″ to Y 21 ″ are the same or different and represent N or CR 1. R 1 Is a hydrogen atom, halogen atom, C 1-6 alkoxy group, aryloxy group, trifluoromethyl group, hydroxy group, C 1-6 alkyl group, C 3-7 cycloalkyl group, C 3-7 cycloalkyl-substituted C 1-4 alkyl group, C 2-6 alkenyl group, C 2-6 alkynyl group, C 1-6 alkoxy group, trifluoromethoxy group, trifluoroethoxy group, C 1-10 alkylcarbonyl group, C 1-2 alkyl a sulfonyl group, a cyano group, a nitro group, an amino group, a mono- or di-substituted amino group, a mono-arylamino group, diarylamino group, carbazole group, C 1-6 alkoxycarbonylamino group, a carbamoyl group, Roh or disubstituted carbamoyl group, a sulfamoyl group, a mono- or di-substituted sulfamoyl group, C 1-6 alkylsulfonylamino group, an aryl group, a heteroaryl group, C 1-6 alkoxycarbonyl group, an aryl-substituted C 1-4 alkoxycarbonyl group , Carboxyl group, 5-tetrazolyl group, sulfo group (—SO 2 OH) or fluorosulfonyl group, provided that the alkyl group, alkenyl group and alkynyl group are halogen, hydroxy, disubstituted amino, aryl substituted C 1- 4 alkyl group, heteroaryl-substituted C 1-4 alkyl group, optionally substituted by 1 to 3 atoms or groups selected from aryl and heteroaryl, and the above aryl group, aryl moiety, heteroaryl group The heteroaryl moiety may be halogen, hydroxy, C 1-6 alkyl, hydroxy C 1-3 alkyl, C 1-6 alkoxy, trifluoromethyl, trifluoromethoxy, trifluoroethoxy, cyano, nitro, amino, mono- or disubstituted amino, carbamoyl, sulfamoyl, C 1-6 Alkylsulfonyl, C 1-3 alkylsulfonylamino, C 1-3 alkylcarbonylamino, methylenedioxy, monoarylamino, diarylamino, carbazole, heteroaryl and aryl (the aryl is a halogen atom, a C 1-6 alkoxy group) , Trifluoromethyl group, hydroxy group, C 1-6 alkyl group, C 3-7 cycloalkyl group, C 3-7 cycloalkyl-substituted C 1-4 alkyl group, C 2-6 alkenyl group, C 2-6 alkynyl group, C 1-6 alkoxy groups, trifluoperazine Methoxy, trifluoroethoxy group 1 which, C 1-10 alkylcarbonyl group, C 1-2 alkylsulfonyl group, a cyano group, selected from a nitro group or an amino group may be mono- or di-substituted) It may be substituted with 4 atoms or groups. Alternatively, two adjacent R 1 groups bonded to any one of adjacent Y 1 to Y 15 , Y 1 ′ to Y 6 ′ , Y 10 ′ to Y 15 ′ , and Y 1 ″ to Y 21 ″. It is that they show a cyclic group which may have a hetero atom a 5- or 6-membered ring together with the carbon atom bonded, Y 1 ~Y 15, Y 1 '~Y 6 Three adjacent R 1 groups bonded to any one of ' , Y 10 ′ to Y 15 ′ , Y 1 ″ to Y 21 ″ together with the carbon atom to which they are bonded are 2 A ring or a tricyclic aromatic cyclic group is shown.
X、X1、X2、X3は同一又は異なってヘテロ原子もしくはその誘導体またはCR1を示す。)
項3. X、X1、X2、X3が、同一又は異なってN、P、As、Si−R1、CR1またはBである、項1に記載の化合物。
項4. 項1、2又は3に記載の化合物を含む、有機発光素子。X, X 1 , X 2 and X 3 are the same or different and each represents a hetero atom or a derivative thereof or CR 1 . )
Item 3. Item 2. The compound according to Item 1, wherein X, X 1 , X 2 and X 3 are the same or different and are N, P, As, Si—R 1 , CR 1 or B.
Item 4. Item 5. An organic light emitting device comprising the compound according to item 1, 2 or 3.
本発明によれば、ホール輸送材料、発光材料、電子輸送材料などの有機ELデバイスに使用するのに適した新規化合物を提供することができる。 ADVANTAGE OF THE INVENTION According to this invention, the novel compound suitable for using for organic EL devices, such as a hole transport material, a luminescent material, and an electron transport material, can be provided.
本発明は、下記一般式(I)で表される化合物を提供するものである。 The present invention provides a compound represented by the following general formula (I).
(式中、X、X1、X2、X3、Z1、Z2は、上記(i)〜(iii)のいずれかである)(Wherein, X, X 1 , X 2 , X 3 , Z 1 , Z 2 are any one of (i) to (iii) above)
一般式(IA1)、(IA2)、(IA3)、(IA4)のいずれかにおいて、X、X1、X2、X3としては、同一又は異なってヘテロ原子もしくはその誘導体またはCR1であり、ヘテロ原子としては、N、P、As、C−R1、Si−R1、B、Ge−R1、Sn−R1、Al、Ga、Pb−R1(R1は前記に定義されるとおりである)、Sb、Bi、In、ランタノイドなどが挙げられ、好ましくはN、P、As、C−R1、Si−R1、B、Ge−R1、Sn−R1、Al、Ga(R1は前記に定義されるとおりである)であり、より好ましくはN、P、As、C−R1、Si−R1、B、(R1は前記に定義されるとおりである)である。ヘテロ原子の誘導体としては、P=O、P=S、P=Se、P(R1)2(R1は前記に定義されるとおりである)、N=O、B−(R1)・M(R1は前記に定義されるとおりである。MはLi、 Na、 K、 Cs、 MgCl、 MgBr、 Bu4Nなどを意味する)などが挙げられる。In any one of the general formulas (IA1), (IA2), (IA3), and (IA4), X, X 1 , X 2 , and X 3 are the same or different and are heteroatoms or derivatives thereof or CR 1 ; Heteroatoms include N, P, As, C—R 1 , Si—R 1 , B, Ge—R 1 , Sn—R 1 , Al, Ga, Pb—R 1 (R 1 is as defined above. Sb, Bi, In, lanthanoid, etc., preferably N, P, As, C—R 1 , Si—R 1 , B, Ge—R 1 , Sn—R 1 , Al, Ga (R 1 is as defined above), more preferably N, P, As, C—R 1 , Si—R 1 , B, (R 1 is as defined above). It is. Heteroatom derivatives include P = O, P = S, P = Se, P (R 1 ) 2 (R 1 is as defined above), N = O, B- (R 1 ). M (R 1 is as defined above. M represents Li, Na, K, Cs, MgCl, MgBr, Bu 4 N, etc.).
Y1〜Y15、Y1’〜Y6’、Y10’〜Y15’、Y1’’〜Y21’’は同一または異なって、各々N(窒素原子)またはCR1を示す。Y1〜Y15、Y1’〜Y6’、Y10’〜Y15’、Y1’’〜Y21’’に結合している複数のR1は、同一であっても異なっていてもよい。Y1〜Y15、Y1’〜Y6’、Y10’〜Y15’、Y1’’〜Y21’’が窒素原子を表す場合、1つの環に3個の窒素原子を有していてもよいが、好ましくは2個以下、より好ましくは1個である。例えば、Y1、Y2、Y3を有する環の場合、Y1=Y2=Y3=Nであってもよいが、Y1、Y2、Y3のうち窒素原子は2個以下が好ましく、窒素原子が1個以下がより好ましい。また、Y1〜Y15、Y1’〜Y6’、Y10’〜Y15’、Y1’’〜Y21’’のうち、窒素原子の総数は、5個以下が好ましく、3個以下がより好ましく、2個以下がさらに好ましい。Y 1 to Y 15 , Y 1 ′ to Y 6 ′ , Y 10 ′ to Y 15 ′ , and Y 1 ″ to Y 21 ″ are the same or different and each represents N (nitrogen atom) or CR 1 . Y 1 ~Y 15, Y 1 ' ~Y 6', Y 10 '~Y 15', a plurality bound to Y 1 '' ~Y 21 '' R 1 is optionally substituted by one or more identical Also good. When Y 1 to Y 15 , Y 1 ′ to Y 6 ′ , Y 10 ′ to Y 15 ′ , and Y 1 ″ to Y 21 ″ represent a nitrogen atom, each ring has three nitrogen atoms. However, it is preferably 2 or less, more preferably 1. For example, in the case of a ring having Y 1 , Y 2 , Y 3 , Y 1 = Y 2 = Y 3 = N may be satisfied, but no more than 2 nitrogen atoms in Y 1 , Y 2 , Y 3 Preferably, 1 or less nitrogen atom is more preferable. Of Y 1 to Y 15 , Y 1 ′ to Y 6 ′ , Y 10 ′ to Y 15 ′ , and Y 1 ″ to Y 21 ″ , the total number of nitrogen atoms is preferably 5 or less, preferably 3 The following is more preferable, and 2 or less is more preferable.
隣接するY1〜Y15、Y1’〜Y6’、Y10’〜Y15’、Y1’’〜Y21’’がCR1である場合、隣接する2つのR1基は、これらが結合している炭素原子(必要に応じてこれらが結合している炭素原子に挟まれる炭素原子を含む場合がある)と一緒になって5員環又は6員環のヘテロ原子を有していてもよい環式基を示す。ここで、隣接する2つのR1基の組合せは、Y1とY2、Y2とY3、Y3とY4、Y4とY5、Y5とY6、Y6とY7、Y7とY8、Y8とY9、Y9とY10、Y10とY11、Y11とY12、Y12とY13、Y13とY14、Y14とY15、
Y1’とY2’、Y2’とY3’、Y3’とY4’、Y4’とY5’、Y5’とY6’、Y10’とY11’、Y11’とY12’、Y12’とY13’、Y13’とY14’、Y14’とY15’、
Y1’’とY2’’、Y2’’とY3’’、Y3’’とY4’’、Y4’’とY5’’、Y5’’とY6’’、Y6’’とY7’’、Y8’’とY9’’、Y9’’とY10’’、Y10’’とY11’’、Y11’’とY12’’、Y12’’とY13’’、Y13’’とY14’’、Y15’’とY16’’、Y16’’とY17’’、Y17’’とY18’’、Y18’’とY19’’、Y19’’とY20’’、Y20’’とY21’’、
に各々含まれる2つのR1基の組合せが挙げられる。「5員環又は6員環のヘテロ原子を有していてもよい環式基」としては、ベンゼン、ジヒドロベンゼン、テトラヒドロベンゼン、シクロペンテン、シクロペンタジエン、フラン、ピラン、ジヒドロフラン、ジヒドロピラン、ジヒドロピロール、ピロール、ジヒドロチオフェン、チオフェン、イミダゾール、チアゾール、オキサゾール、ピリジン、ジヒドロピリジン、ピリミジン、ジヒドロピリミジン、ピリダジン、ジヒドロピリダジンが挙げられる。When adjacent Y 1 to Y 15 , Y 1 ′ to Y 6 ′ , Y 10 ′ to Y 15 ′ , and Y 1 ″ to Y 21 ″ are CR 1 , two adjacent R 1 groups are Together with the carbon atom to which they are bonded (which may contain carbon atoms sandwiched between the carbon atoms to which they are bonded if necessary) and having a 5-membered or 6-membered heteroatom An optional cyclic group is shown. Here, the combination of two adjacent R 1 groups is Y 1 and Y 2 , Y 2 and Y 3 , Y 3 and Y 4 , Y 4 and Y 5 , Y 5 and Y 6 , Y 6 and Y 7 , Y 7 and Y 8, Y 8 and Y 9, Y 9 and Y 10, Y 10 and Y 11, Y 11 and Y 12, Y 12 and Y 13, Y 13 and Y 14, Y 14 and Y 15,
Y 1 'and Y 2', Y 2 'and Y 3', Y 3 'and Y 4', Y 4 'and Y 5', 'Y 6 and' Y 5, Y 10 'and Y 11', Y 11 ' And Y 12' , Y 12 ' and Y 13' , Y 13 ' and Y 14' , Y 14 ' and Y 15' ,
Y 1 '' and Y 2 '' , Y 2 '' and Y 3 '' , Y 3 '' and Y 4 '' , Y 4 '' and Y 5 '' , Y 5 '' and Y 6 '' , Y 6 '' and Y 7 '' , Y 8 '' and Y 9 '' , Y 9 '' and Y 10 '' , Y 10 '' and Y 11 '' , Y 11 '' and Y 12 '' , Y 12 '' and Y 13 '' , Y 13 '' and Y 14 '' , Y 15 '' and Y 16 '' , Y 16 '' and Y 17 '' , Y 17 '' and Y 18 '' , Y 18 '' and Y 19 '' , Y 19 '' and Y 20 '' , Y 20 '' and Y 21 '' ,
The combination of two R < 1 > groups each contained in is mentioned. Examples of the “cyclic group optionally having a 5-membered ring or 6-membered hetero atom” include benzene, dihydrobenzene, tetrahydrobenzene, cyclopentene, cyclopentadiene, furan, pyran, dihydrofuran, dihydropyran, dihydropyrrole. , Pyrrole, dihydrothiophene, thiophene, imidazole, thiazole, oxazole, pyridine, dihydropyridine, pyrimidine, dihydropyrimidine, pyridazine, dihydropyridazine.
隣接するY1〜Y15、Y1’〜Y6’、Y10’〜Y15’、Y1’’〜Y21’’がCR1である場合、隣接する3つのR1基は、これらが結合している炭素原子と一緒になって2環または3環の芳香族環式基を示す。ここで、隣接する3つのR1基の組合せは、Y1〜Y15に関しては、Y1とY2とY3、Y2とY3とY4、Y3とY4とY5、Y4とY5とY6、Y5とY6とY7、Y6とY7とY8、Y7とY8とY9、Y8とY9とY10、Y9とY10とY11、Y10とY11とY12、Y11とY12とY13、Y12とY13とY14、Y13とY14とY15に各々含まれる3つのR1基の組合せが挙げられる。Y1’〜Y6’、Y10’〜Y15’、Y1’’〜Y21’’についても同様な3つのR1基の組合せが挙げられる。When adjacent Y 1 to Y 15 , Y 1 ′ to Y 6 ′ , Y 10 ′ to Y 15 ′ , and Y 1 ″ to Y 21 ″ are CR 1 , these three adjacent R 1 groups are Represents a bicyclic or tricyclic aromatic cyclic group together with the carbon atom to which is bonded. Here, the combination of the three adjacent R 1 groups which may, for Y 1 ~Y 15, Y 1 and Y 2 and Y 3, Y 2 and Y 3 and Y 4, Y 3 and Y 4 and Y 5, Y 4 and Y 5 and Y 6 , Y 5 and Y 6 and Y 7 , Y 6 and Y 7 and Y 8 , Y 7 and Y 8 and Y 9 , Y 8 and Y 9 and Y 10 , Y 9 and Y 10 and Y 11, Y 10 and the combination of Y 11 and Y 12, Y 11 and Y 12 and Y 13, Y 12 and Y 13 and Y 14, Y 13 and Y 14 and each three R 1 groups contained in Y 15 is Can be mentioned. The same combination of three R 1 groups may be mentioned for Y 1 ′ to Y 6 ′ , Y 10 ′ to Y 15 ′ , and Y 1 ″ to Y 21 ″ .
「2環または3環の芳香族環式基」としては、ナフタレン、インデン、フェナントレン、アントラセン、フルオレン、アセナフテン、フェナレンが挙げられる。 Examples of the “bicyclic or tricyclic aromatic cyclic group” include naphthalene, indene, phenanthrene, anthracene, fluorene, acenaphthene, and phenalene.
本明細書では、「C1−6アルキルカルボニル」のように炭素原子数を規定しているが、この炭素原子数は直後に続く基又は部分のみを修飾する。したがって、上記の場合、C1−6はアルキルのみを修飾するので、「C1アルキルカルボニル」とはアセチルに該当する。In the present specification, the number of carbon atoms is defined as “C 1-6 alkylcarbonyl”, but this number of carbon atoms modifies only the group or moiety that immediately follows. Therefore, in the above case, since C 1-6 modifies only alkyl, “C 1 alkylcarbonyl” corresponds to acetyl.
アルキル基及びアルキル部分は、直鎖状でも分枝鎖状でもよい。 The alkyl group and the alkyl moiety may be linear or branched.
本明細書でアルキル部分とは、C1−2アルキルスルホニル基、C1−6アルキルスルホニルアミノ基、アリール置換C1−4アルキル基、ヘテロアリール置換C1−4アルキル基及びC1−10アルキルカルボニル基における各アルキル基だけでなく、C1−6アルコキシカルボニルアミノ基、C1−6アルコキシカルボニル基及びC1−6アルコキシ基中のアルコキシ(O−アルキル基)中のアルキル基、モノ若しくはジ置換アミノ基、モノ若しくはジ置換スルファモイル基、ジ置換アミノの置換基であるアルキル基を包含する。In this specification, the alkyl moiety means a C 1-2 alkylsulfonyl group, a C 1-6 alkylsulfonylamino group, an aryl-substituted C 1-4 alkyl group, a heteroaryl-substituted C 1-4 alkyl group and a C 1-10 alkyl. Not only each alkyl group in the carbonyl group, but also an alkyl group in a C 1-6 alkoxycarbonylamino group, a C 1-6 alkoxycarbonyl group, and an alkoxy (O-alkyl group) in a C 1-6 alkoxy group, mono- or di- A substituted amino group, a mono- or di-substituted sulfamoyl group, and an alkyl group that is a substituent of a di-substituted amino are included.
アリール部分とは、アリール置換C1−4アルコキシカルボニル基、モノアリールアミノ基、ジアリールアミノ基及びアリール置換C1−4アルキル基のアリール基を意味する。The aryl moiety means an aryl group of an aryl-substituted C 1-4 alkoxycarbonyl group, a monoarylamino group, a diarylamino group, and an aryl-substituted C 1-4 alkyl group.
ヘテロアリール部分とは、ヘテロアリール置換C1−4アルキル基のヘテロアリール基を意味する。A heteroaryl moiety refers to a heteroaryl group of a heteroaryl-substituted C 1-4 alkyl group.
「ハロゲン原子」とは、フッ素、塩素、臭素、ヨウ素を意味するが、フッ素、塩素、臭素が好ましい。 “Halogen atom” means fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine.
「C1−10アルキル基」とは、直鎖状、分枝鎖状又は環状のいずれでもよく、例えば、メチル、エチル、n−プロピル、イソプロピル、n−ブチル、イソブチル、tert−ブチル、n−ペンチル、イソペンチル、ヘキシル、ヘプチル、オクチル、ノニル及びデシルが挙げられる。The “C 1-10 alkyl group” may be any of linear, branched or cyclic, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n- Examples include pentyl, isopentyl, hexyl, heptyl, octyl, nonyl and decyl.
「C1−6アルキル基」とは、直鎖状又は分枝鎖状のいずれでもよく。例えば、メチル、エチル、n−プロピル、イソプロピル、n−ブチル、イソブチル、tert−ブチル、n−ペンチル、イソペンチル、ヘキシルが挙げられる。The “C 1-6 alkyl group” may be linear or branched. Examples thereof include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl and hexyl.
「C1−4アルキル基」とは、直鎖状又は分枝鎖状のいずれでもよく。例えば、メチル、エチル、n−プロピル、イソプロピル、n−ブチル、イソブチル、tert−ブチルが挙げられる。The “C 1-4 alkyl group” may be linear or branched. Examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl.
「C1−3アルキル基」とは、直鎖状又は分枝鎖状のいずれでもよく。例えば、メチル、エチル、n−プロピル、イソプロピルが挙げられる。The “C 1-3 alkyl group” may be linear or branched. For example, methyl, ethyl, n-propyl, and isopropyl are mentioned.
「C1−2アルキル基」は、メチル又はエチルである。A “C 1-2 alkyl group” is methyl or ethyl.
「C3−7シクロアルキル基」としては、シクロプロピル、シクロブチル、シクロペンチル、シクロヘキシル及びシクロヘプチルが挙げられる。 Examples of the “C 3-7 cycloalkyl group” include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl.
「C3−7シクロアルキル置換C1−4アルキル基」としては、シクロプロピルメチル、シクロブチルメチル、シクロペンチルメチル、シクロヘキシルメチル及びシクロヘプチルメチルが挙げられる。 Examples of the “C 3-7 cycloalkyl-substituted C 1-4 alkyl group” include cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl and cycloheptylmethyl.
「C2−10アルケニル基」とは、直鎖状、分枝鎖状又は環状のいずれでもよく、二重結合を少なくとも1個有するものを意味し、例えばビニル、アリル、1−プロペニル、2−メチル−2−プロペニル、イソプロペニル、1−、2−若しくは3−ブテニル、2−、3−若しくは4−ペンテニル、2−メチル−2−ブテニル、3−メチル−2−ブテニル、5−ヘキセニル、1−シクロペンテニル、1−シクロヘキセニル、3−メチル−3−ブテニルが挙げられる。The “C 2-10 alkenyl group” may be any of linear, branched or cyclic, and means one having at least one double bond, such as vinyl, allyl, 1-propenyl, 2- Methyl-2-propenyl, isopropenyl, 1-, 2- or 3-butenyl, 2-, 3- or 4-pentenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 5-hexenyl, 1 -Cyclopentenyl, 1-cyclohexenyl, 3-methyl-3-butenyl.
「C2−6アルケニル基」とは、直鎖状、分枝鎖状又は環状のいずれでもよく、二重結合を少なくとも1個有するものを意味し、例えばビニル、アリル、1−プロペニル、2−メチル−2−プロペニル、イソプロペニル、1−、2−若しくは3−ブテニル、2−、3−若しくは4−ペンテニル、2−メチル−2−ブテニル、3−メチル−2−ブテニル、5−ヘキセニル、1−シクロペンテニル、1−シクロヘキセニル、3−メチル−3−ブテニルが挙げられる。The “C 2-6 alkenyl group” may be linear, branched or cyclic, and means one having at least one double bond, such as vinyl, allyl, 1-propenyl, 2- Methyl-2-propenyl, isopropenyl, 1-, 2- or 3-butenyl, 2-, 3- or 4-pentenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 5-hexenyl, 1 -Cyclopentenyl, 1-cyclohexenyl, 3-methyl-3-butenyl.
「C2−10アルキニル基」とは、直鎖状、分枝鎖状又は環状のいずれでもよく、三重結合を少なくとも1個有するものを意味し、例えばエチニル、1−若しくは2−プロピニル、1−、2−若しくは3−ブチニル、1−メチル−2−プロピニルが挙げられる。The “C 2-10 alkynyl group” may be linear, branched or cyclic, and means one having at least one triple bond, such as ethynyl, 1- or 2-propynyl, 1- , 2- or 3-butynyl, 1-methyl-2-propynyl.
「C2−6アルキニル基」とは、直鎖状、分枝鎖状又は環状のいずれでもよく、三重結合を少なくとも1個有するものを意味し、例えばエチニル、1−若しくは2−プロピニル、1−、2−若しくは3−ブチニル、1−メチル−2−プロピニルが挙げられる。The “C 2-6 alkynyl group” may be linear, branched or cyclic, and means one having at least one triple bond, such as ethynyl, 1- or 2-propynyl, 1- , 2- or 3-butynyl, 1-methyl-2-propynyl.
モノ若しくはジ置換アミノ基、モノ若しくはジ置換カルバモイル基又はモノ若しくはジ置換スルファモイル基における「モノ置換」とは、アミノ基、カルバモイル基又はスルファモイル基の窒素原子に結合する水素原子の1個がC1−6アルキルで置換されていることを意味し、「ジ置換」とは、アミノ基、カルバモイル基又はスルファモイル基の窒素原子に結合する水素原子の2個が同一又は異なるC1−6アルキルで置換されているか、或いは3〜8員、好ましくは5又は6員の含窒素環式基で置換されていることを意味する。含窒素環式基としては、モルホリノ、1−ピロリジニル、ピペリジノ及び4−メチル−1−ピペラジニルが挙げられる。“Mono-substituted” in a mono- or di-substituted amino group, mono- or di-substituted carbamoyl group or mono- or di-substituted sulfamoyl group means that one hydrogen atom bonded to the nitrogen atom of the amino group, carbamoyl group or sulfamoyl group is C 1. The term “disubstituted” means that two hydrogen atoms bonded to the nitrogen atom of the amino group, carbamoyl group or sulfamoyl group are substituted with the same or different C 1-6 alkyl. Or substituted with a 3- to 8-membered, preferably 5- or 6-membered, nitrogen-containing cyclic group. Nitrogen-containing cyclic groups include morpholino, 1-pyrrolidinyl, piperidino and 4-methyl-1-piperazinyl.
C1−6アルキルでモノ置換されたアミノ基としては、メチルアミノ、エチルアミノ、n−プロピルアミノ、イソプロピルアミノ、n−ブチルアミノ、イソブチルアミノ、tert−ブチルアミノ、n−ペンチルアミノ、イソペンチルアミノ、ヘキシルアミノが挙げられる。The amino group monosubstituted by C 1-6 alkyl includes methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, isobutylamino, tert-butylamino, n-pentylamino, isopentylamino. And hexylamino.
C1−6アルキルでジ置換されたアミノ基としては、ジメチルアミノ、ジエチルアミノ、ジn−プロピルアミノ、ジイソプロピルアミノ、ジn−ブチルアミノ、ジイソブチルアミノ、ジtert−ブチルアミノ、ジn−ペンチルアミノ、ジイソペンチルアミノ、ジヘキシルアミノが挙げられる。 Examples of the amino group disubstituted with C 1-6 alkyl include dimethylamino, diethylamino, di-n-propylamino, diisopropylamino, di-n-butylamino, diisobutylamino, ditert-butylamino, di-n-pentylamino, Examples include diisopentylamino and dihexylamino.
C1−6アルキルでモノ置換されたカルバモイル基としては、メチルカルバモイル、エチルカルバモイル、n−プロピルカルバモイル、イソプロピルカルバモイル、n−ブチルカルバモイル、イソブチルカルバモイル、tert−ブチルカルバモイル、n−ペンチルカルバモイル、イソペンチルカルバモイル、ヘキシルカルバモイルが挙げられる。Examples of the carbamoyl group mono-substituted with C 1-6 alkyl include methylcarbamoyl, ethylcarbamoyl, n-propylcarbamoyl, isopropylcarbamoyl, n-butylcarbamoyl, isobutylcarbamoyl, tert-butylcarbamoyl, n-pentylcarbamoyl, isopentylcarbamoyl And hexylcarbamoyl.
C1−6アルキルでジ置換されたカルバモイル基としては、ジメチルカルバモイル、ジエチルカルバモイル、ジn−プロピルカルバモイル、ジイソプロピルカルバモイル、ジn−ブチルカルバモイル、ジイソブチルカルバモイル、ジtert−ブチルカルバモイル、ジn−ペンチルカルバモイル、ジイソペンチルカルバモイル、ジヘキシルカルバモイルが挙げられる。Examples of the carbamoyl group di-substituted with C 1-6 alkyl include dimethylcarbamoyl, diethylcarbamoyl, di-n-propylcarbamoyl, diisopropylcarbamoyl, di-n-butylcarbamoyl, diisobutylcarbamoyl, ditert-butylcarbamoyl, din-pentylcarbamoyl. , Diisopentylcarbamoyl, and dihexylcarbamoyl.
C1−6アルキルでモノ置換されたスルファモイル基としては、メチルスルファモイル、エチルスルファモイル、n−プロピルスルファモイル、イソプロピルスルファモイル、n−ブチルスルファモイル、イソブチルスルファモイル、tert−ブチルスルファモイル、n−ペンチルスルファモイル、イソペンチルスルファモイル、ヘキシルスルファモイルが挙げられる。The sulfamoyl group mono-substituted with C 1-6 alkyl includes methylsulfamoyl, ethylsulfamoyl, n-propylsulfamoyl, isopropylsulfamoyl, n-butylsulfamoyl, isobutylsulfamoyl, tert -Butylsulfamoyl, n-pentylsulfamoyl, isopentylsulfamoyl, hexylsulfamoyl.
C1−6アルキルでジ置換されたスルファモイル基としては、ジメチルスルファモイル、ジエチルスルファモイル、ジn−プロピルスルファモイル、ジイソプロピルスルファモイル、ジn−ブチルスルファモイル、ジイソブチルスルファモイル、ジtert−ブチルスルファモイル、ジn−ペンチルスルファモイル、ジイソペンチルスルファモイル、ジヘキシルスルファモイルが挙げられる。Examples of the sulfamoyl group disubstituted with C 1-6 alkyl include dimethylsulfamoyl, diethylsulfamoyl, di-n-propylsulfamoyl, diisopropylsulfamoyl, di-n-butylsulfamoyl, diisobutylsulfamoyl. Di-tert-butylsulfamoyl, di-n-pentylsulfamoyl, diisopentylsulfamoyl, dihexylsulfamoyl.
「アリール基」とは、5又は6員の芳香族炭化水素環からなる単環又は多環系の基を意味し、具体例としては、フェニル、ナフチル、フルオレニル、アントリル、ビフェニリル、テトラヒドロナフチル、クロマニル、2,3−ジヒドロ−1,4−ジオキサナフタレニル、インダニル及びフェナントリルが挙げられる。 The “aryl group” means a monocyclic or polycyclic group composed of a 5- or 6-membered aromatic hydrocarbon ring, and specific examples include phenyl, naphthyl, fluorenyl, anthryl, biphenylyl, tetrahydronaphthyl, chromanyl. 2,3-dihydro-1,4-dioxanaphthalenyl, indanyl and phenanthryl.
「アリーレン(arylene)基」とは、5又は6員の芳香族炭化水素環からなる単環又は多環系の2価基を意味し、具体例としては、フェニレン及びナフチレンが挙げられる。 The “arylene group” means a monocyclic or polycyclic divalent group composed of a 5- or 6-membered aromatic hydrocarbon ring, and specific examples thereof include phenylene and naphthylene.
「ヘテロアリール基」とは、N、O及びSから選択される1〜3個のヘテロ原子を含む、5又は6員の芳香環からなる単環又は多環系の基を意味し、多環系の場合には少なくとも1つの環が芳香環であればよい。具体例としては、フリル、チエニル、ピロリル、イミダゾリル、ピラゾリル、オキサゾリル、チアゾリル、イソオキサゾリル、イソチアゾリル、ピリジル、ピラジニル、ピリミジニル、ピリダジニル、インドリル、キノリル、イソキノリル、カルバゾリル、シロール,ベンゾ[b]シロール,ベンゾ[b]フリル、ベンゾ[b]チエニル、ジベンゾ[b,d]フリル、ジベンゾ[b,d]チエニル、及びベンズイミダゾリルが挙げられる。 “Heteroaryl group” means a monocyclic or polycyclic group consisting of a 5- or 6-membered aromatic ring containing 1 to 3 heteroatoms selected from N, O and S. In the case of a system, at least one ring may be an aromatic ring. Specific examples include furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolyl, quinolyl, isoquinolyl, carbazolyl, silole, benzo [b] silole, benzo [b ] Furyl, benzo [b] thienyl, dibenzo [b, d] furyl, dibenzo [b, d] thienyl, and benzimidazolyl.
アリールオキシとしては、フェニルオキシ、ナフチルオキシ、フルオレニルオキシ、アントリルオキシ、ビフェニリルオキシ、テトラヒドロナフチルオキシ、クロマニルオキシ、2,3−ジヒドロ−1,4−ジオキサナフタレニルオキシ、インダニルオキシ及びフェナントリルオキシが挙げられる。 Aryloxy includes phenyloxy, naphthyloxy, fluorenyloxy, anthryloxy, biphenylyloxy, tetrahydronaphthyloxy, chromanoxy, 2,3-dihydro-1,4-dioxanaphthalenyloxy, inda Nyloxy and phenanthryloxy are mentioned.
アリール置換C1−4アルコキシとしては、ベンジルオキシ、ナフチルメチルオキシ、フルオレニルメチルオキシ、アントリルメチルオキシ、ビフェニリルメチルオキシ、テトラヒドロナフチルメチルオキシ、クロマニルメチルオキシ、2,3−ジヒドロ−1,4−ジオキサナフタレニルメチルオキシ、インダニルメチルオキシ及びフェナントリルメチルオキシ、フェネチルオキシ、ナフチルエチルオキシ、フルオレニルエチルオキシ、アントリルエチルオキシ、ビフェニリルエチルオキシ、テトラヒドロナフチルエチルオキシ、クロマニルエチルオキシ、2,3−ジヒドロ−1,4−ジオキサナフタレニルエチルオキシ、インダニルエチルオキシ及びフェナントリルエチルオキシが挙げられる。Aryl-substituted C 1-4 alkoxy includes benzyloxy, naphthylmethyloxy, fluorenylmethyloxy, anthrylmethyloxy, biphenylylmethyloxy, tetrahydronaphthylmethyloxy, chromanylmethyloxy, 2,3-dihydro-1 , 4-Dioxanaphthalenylmethyloxy, indanylmethyloxy and phenanthrylmethyloxy, phenethyloxy, naphthylethyloxy, fluorenylethyloxy, anthrylethyloxy, biphenylylethyloxy, tetrahydronaphthylethyloxy, Examples include chromanylethyloxy, 2,3-dihydro-1,4-dioxanaphthalenylethyloxy, indanylethyloxy and phenanthrylethyloxy.
例えば、C1−6アルコキシ基としては、メトキシ、エトキシ、プロポキシ、イソプロポキシ、ブトキシ、イソブトキシ、tert−ブトキシ、ペンチルオキシ、イソペンチルオキシ及びヘキシルオキシが挙げられる。For example, C 1-6 alkoxy groups include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, tert-butoxy, pentyloxy, isopentyloxy and hexyloxy.
トリフルオロエトキシ基としては、CF3CH2O−が好ましい。As the trifluoroethoxy group, CF 3 CH 2 O— is preferable.
C1−2アルキルスルホニル基としては、メチルスルホニル及びエチルスルホニルが挙げられる。Examples of the C 1-2 alkylsulfonyl group include methylsulfonyl and ethylsulfonyl.
C1−6アルコキシカルボニルアミノ基としては、メトキシカルボニルアミノ、エトキシカルボニルアミノ、プロポキシカルボニルアミノ、イソプロポキシカルボニルアミノ、ブトキシカルボニルアミノ、イソブトキシカルボニルアミノ、tert−ブトキシカルボニルアミノ、ペンチルオキシカルボニルアミノ、イソペンチルオキシカルボニルアミノ及びヘキシルオキシカルボニルアミノが挙げられる。The C 1-6 alkoxycarbonylamino group includes methoxycarbonylamino, ethoxycarbonylamino, propoxycarbonylamino, isopropoxycarbonylamino, butoxycarbonylamino, isobutoxycarbonylamino, tert-butoxycarbonylamino, pentyloxycarbonylamino, isopentyl. Examples include oxycarbonylamino and hexyloxycarbonylamino.
C1−6アルキルスルホニルアミノ基としては、メチルスルホニルアミノ、エチルスルホニルアミノ、n−プロピルスルホニルアミノ、イソプロピルスルホニルアミノ、n−ブチルスルホニルアミノ、イソブチルスルホニルアミノ、tert−ブチルスルホニルアミノ、n−ペンチルスルホニルアミノ、イソペンチルスルホニルアミノ、ヘキシルスルホニルアミノが挙げられる。As the C 1-6 alkylsulfonylamino group, methylsulfonylamino, ethylsulfonylamino, n-propylsulfonylamino, isopropylsulfonylamino, n-butylsulfonylamino, isobutylsulfonylamino, tert-butylsulfonylamino, n-pentylsulfonylamino , Isopentylsulfonylamino, and hexylsulfonylamino.
C1−6アルコキシカルボニル基としては、メトキシカルボニル、エトキシカルボニル、プロポキシカルボニル、イソプロポキシカルボニル、ブトキシカルボニル、イソブトキシカルボニル、tert−ブトキシカルボニル、ペンチルオキシカルボニル、イソペンチルオキシカルボニル及びヘキシルオキシカルボニルが挙げられる。C 1-6 alkoxycarbonyl groups include methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, isobutoxycarbonyl, tert-butoxycarbonyl, pentyloxycarbonyl, isopentyloxycarbonyl and hexyloxycarbonyl. .
アリール置換C1−4アルコキシカルボニル基としては、フェニルメチルオキシカルボニル、ナフチルメチルオキシカルボニル、フルオレニルメチルオキシカルボニル、アントリルメチルオキシカルボニル、ビフェニリルメチルオキシカルボニル、テトラヒドロナフチルメチルオキシカルボニル、クロマニルメチルオキシカルボニル、2,3−ジヒドロ−1,4−ジオキサナフタレニルメチルオキシカルボニル、インダニルメチルオキシカルボニル及びフェナントリルメチルオキシカルボニルが挙げられる。The aryl-substituted C 1-4 alkoxycarbonyl group includes phenylmethyloxycarbonyl, naphthylmethyloxycarbonyl, fluorenylmethyloxycarbonyl, anthrylmethyloxycarbonyl, biphenylylmethyloxycarbonyl, tetrahydronaphthylmethyloxycarbonyl, chromanylmethyl. Examples include oxycarbonyl, 2,3-dihydro-1,4-dioxanaphthalenylmethyloxycarbonyl, indanylmethyloxycarbonyl, and phenanthrylmethyloxycarbonyl.
アリール置換C1−4アルキル基としては、ベンジル、ナフチルメチル、フルオレニルメチル、アントリルメチル、ビフェニリルメチル、テトラヒドロナフチルメチル、クロマニルメチル、2,3−ジヒドロ−1,4−ジオキサナフタレニルメチル、インダニルメチル及びフェナントリルメチル、フェネチル、ナフチルエチル、フルオレニルエチル、アントリルエチル、ビフェニリルエチル、テトラヒドロナフチルエチル、クロマニルエチル、2,3−ジヒドロ−1,4−ジオキサナフタレニルエチル、インダニルエチル及びフェナントリルエチルが挙げられる。Examples of the aryl-substituted C 1-4 alkyl group include benzyl, naphthylmethyl, fluorenylmethyl, anthrylmethyl, biphenylylmethyl, tetrahydronaphthylmethyl, chromanylmethyl, 2,3-dihydro-1,4-dioxanaphtha Renylmethyl, indanylmethyl and phenanthrylmethyl, phenethyl, naphthylethyl, fluorenylethyl, anthrylethyl, biphenylylethyl, tetrahydronaphthylethyl, chromanylethyl, 2,3-dihydro-1,4-dio Xanaphthalenylethyl, indanylethyl and phenanthrylethyl.
ヘテロアリール置換C1−4アルキル基としては、フリルメチル、チエニルメチル、ピロリルメチル、イミダゾリルメチル、ピラゾリルメチル、オキサゾリルメチル、チアゾリルメチル、イソオキサゾリルメチル、イソチアゾリルメチル、ピリジルメチル、ピラジニルメチル、ピリミジニルメチル、ピリダジニルメチル、インドリルメチル、キノリルメチル、イソキノリルメチル、ベンゾ[b]チエニルメチル及びベンズイミダゾリルメチル、フリルエチル、チエニルエチル、ピロリルエチル、イミダゾリルエチル、ピラゾリルエチル、オキサゾリルエチル、チアゾリルエチル、イソオキサゾリルエチル、イソチアゾリルエチル、ピリジルエチル、ピラジニルエチル、ピリミジニルエチル、ピリダジニルエチル、インドリルエチル、キノリルエチル、イソキノリルエチル、ベンゾ[b]チエニルエチル及びベンズイミダゾリルエチルが挙げられる。Heteroaryl-substituted C 1-4 alkyl groups include furylmethyl, thienylmethyl, pyrrolylmethyl, imidazolylmethyl, pyrazolylmethyl, oxazolylmethyl, thiazolylmethyl, isoxazolylmethyl, isothiazolylmethyl, pyridylmethyl, pyrazinylmethyl, pyrimidinyl Methyl, pyridazinylmethyl, indolylmethyl, quinolylmethyl, isoquinolylmethyl, benzo [b] thienylmethyl and benzimidazolylmethyl, furylethyl, thienylethyl, pyrrolylethyl, imidazolylethyl, pyrazolylethyl, oxazolylethyl, thiazolylethyl , Isoxazolylethyl, isothiazolylethyl, pyridylethyl, pyrazinylethyl, pyrimidinylethyl, pyridazinylethyl, indolylethyl, quinolyl Examples include ethyl, isoquinolylethyl, benzo [b] thienylethyl, and benzimidazolylethyl.
C1−10アルキルカルボニル基としては、アセチル、プロピオニル、ブチリル、ペンチルカルボニル、ヘキシルカルボニル、ヘプチルカルボニル、オクチルカルボニル、ノニルカルボニル、デシルカルボニルが挙げられる。Examples of the C 1-10 alkylcarbonyl group include acetyl, propionyl, butyryl, pentylcarbonyl, hexylcarbonyl, heptylcarbonyl, octylcarbonyl, nonylcarbonyl, and decylcarbonyl.
モノアリールアミノとしては、フェニルアミノ、トルイルアミノ、ナフチルアミノが挙げられる。 Monoarylamino includes phenylamino, toluylamino, and naphthylamino.
ジアリールアミノとしては、ジフェニルアミノ、ナフチルフェニルアミノ、ジナフチルアミノが挙げられる。 Examples of diarylamino include diphenylamino, naphthylphenylamino, and dinaphthylamino.
本発明の好ましい骨格として、以下の1〜12を例示する。 The following 1 to 12 are exemplified as preferred skeletons of the present invention.
次に、本発明の化合物の製造方法について説明する。 Next, the manufacturing method of the compound of this invention is demonstrated.
本発明の化合物は、以下のスキーム1に従い合成することができる。
<スキーム1>The compound of the present invention can be synthesized according to the following scheme 1.
<Scheme 1>
式中、I/Brは、IまたはBrを意味する。 In the formula, I / Br means I or Br.
反応は、式(1)の化合物1モルに対し、n-BuLiを1モル程度、次いで式(2)の化合物を2モル〜過剰量使用し、溶媒中−78℃〜室温程度の温度下に30分〜24時間撹拌し、その後、その溶液にI2あるいはN-ブロモスクシンイミド(NBS)を1モル〜過剰量加えることで、目的とする式(3)の化合物を得ることができる。溶媒としては、無水ジエチルエーテル、無水THFなどの無水エーテル系溶媒かベンゼン、トルエン、キシレン、メシチレンなどの芳香族炭化水素系溶媒が用いられる。In the reaction, about 1 mol of n-BuLi is used per 1 mol of the compound of formula (1), then 2 mol to an excess amount of the compound of formula (2) is used, and the temperature is about −78 ° C. to room temperature in a solvent. The mixture is stirred for 30 minutes to 24 hours, and then 1 mole to excess of I 2 or N-bromosuccinimide (NBS) is added to the solution to obtain the target compound of formula (3). As the solvent, an anhydrous ether solvent such as anhydrous diethyl ether or anhydrous THF or an aromatic hydrocarbon solvent such as benzene, toluene, xylene or mesitylene is used.
式(4)の化合物1モルに対し、Mgを1モル〜過剰量と式(5)の化合物を1モル〜過剰量使用し、溶媒中室温〜溶媒の沸騰する程度の温度下に30分〜24時間撹拌し、その後、その溶液にI2あるいはN-ブロモスクシンイミド(NBS)を1モル〜過剰量加えることで、目的とする式(6)の化合物を得ることができる。溶媒としては、無水THF、無水アニソールなどの無水エーテル系溶媒が用いられる。Using 1 mol to an excess amount of Mg and 1 mol to an excess amount of a compound of formula (5) with respect to 1 mol of the compound of the formula (4), the solvent is used at room temperature to a temperature at which the solvent boils for 30 minutes to Stir for 24 hours, and then add 1 mol or excess of I 2 or N-bromosuccinimide (NBS) to the solution to obtain the desired compound of formula (6). As the solvent, anhydrous ether solvents such as anhydrous THF and anhydrous anisole are used.
式(3) 、(3’)または(6)の化合物に溶媒中n-BuLiあるいはt-BuLiとXcompoundを加え、−78℃〜溶媒の沸騰する程度の温度下に30分〜24時間反応させることにより目的とする式(6) 、(7)または(8)の化合物を得ることができる。溶媒としては、ベンゼン、トルエン、キシレン、メシチレンなどの芳香族炭化水素系溶媒、またはクロロベンゼン、ジクロロベンゼンなどのハロゲン化芳香族炭化水素溶媒、またはジクロロメタン,ジクロロエタンなどのハロゲン化炭化水素溶媒が用いられる。反応は式(3) 、(3’)または(6)の化合物1モルに対しn-BuLiを1モル〜過剰量あるいはt-BuLiを2モル〜過剰量使用して式(3) 、(3’)または(6)の化合物のI(ヨウ素)基あるいはBr(臭素)基を引き抜き、次いでX compoundを1モル〜過剰量加え、以下に示すように処理することで、式(7) 、(8)または(9)の化合物を得る。 N-BuLi or t-BuLi and Xcompound are added to the compound of the formula (3), (3 ') or (6) in a solvent, and the reaction is carried out at a temperature from -78 ° C to the boiling point of the solvent for 30 minutes to 24 hours. As a result, the desired compound of the formula (6), (7) or (8) can be obtained. As the solvent, aromatic hydrocarbon solvents such as benzene, toluene, xylene and mesitylene, halogenated aromatic hydrocarbon solvents such as chlorobenzene and dichlorobenzene, and halogenated hydrocarbon solvents such as dichloromethane and dichloroethane are used. The reaction is carried out using 1 mole to excess of n-BuLi or 2 mole to excess of t-BuLi per mole of the compound of formula (3), (3 ') or (6). The compound of formula (7), (6), (6) is withdrawn from the I (iodine) group or Br (bromine) group, and then X compound is added in a molar amount to an excess amount and treated as shown below. The compound of 8) or (9) is obtained.
X compoundは、XがP(リン)の場合、PCl(NMe2)2、PCl(NEt2)2、PCl(NiPr2)2、PCl(OEt)2、PCl(OMe)2、PCl3、PBr3などの化合物を使用し、その後、硫黄(S)とAlCl3やAlBr3やBF3・Et2OやBCl3使用して、「P=S」の化合物が得られる。更に、PEt3やPBu3やP(tBu)3などを使用して硫黄(S)を取り除き目的とするX=Pの化合物に導くことができる。また、X=Pの化合物に過酸化水素などを使用する事でXが「P=O」の化合物が得られる。X compound is, when X is P (phosphorus), PCl (NMe 2 ) 2 , PCl (NEt 2 ) 2 , PCl (NiPr 2 ) 2 , PCl (OEt) 2 , PCl (OMe) 2 , PCl 3 , PBr Using a compound such as 3 , then using sulfur (S) and AlCl 3 , AlBr 3 , BF 3 .Et 2 O or BCl 3 , a compound “P═S” is obtained. Furthermore, PEt 3 , PBu 3 , P (tBu) 3, etc. can be used to remove sulfur (S) and lead to the desired X = P compound. Further, by using hydrogen peroxide or the like for the compound of X = P, a compound of X = “P═O” can be obtained.
X compoundは、XがN(窒素)の場合、H2NOTs、H2NOMs、H2NOTf、H2NONf、H2NCl、HNCl2、NCl3、などの化合物を使用し、その後、Pd(OAc)2と酸化剤(Cu(OAc)2やPhI(OAc)2)を使用して、目的とするX=Nの化合物に導くことができる。また、X=Nの化合物に過酸化水素などを使用する事でXが「N=O」の化合物が得られる。When X is N (nitrogen), X compound is a compound such as H 2 NOTs, H 2 NOMs, H 2 NOTf, H 2 NONf, H 2 NCl, HNCl 2 , NCl 3 , and then Pd ( OAc) 2 and an oxidizing agent (Cu (OAc) 2 or PhI (OAc) 2 ) can be used to lead to the desired X = N compound. Further, by using hydrogen peroxide or the like as a compound where X = N, a compound where X is “N═O” can be obtained.
X compoundは、XがAs(ヒ素)の場合、AsCl(NEt2)2、AsCl(NiPr2)2、AsCl(OEt)2、AsCl(OMe)2、AsCl3、AsBr3などの化合物を使用し、その後、硫黄(S)とLiIとAlCl3やAlBr3やBF3・Et2OやBCl3を使用して、「As=S」の化合物が得られる。更に、PBu3やP(tBu)3などを使用して硫黄(S)を取り除き目的とするX=Asの化合物に導くことができる。また、X=Asの化合物に過酸化水素、MCPBAなどを使用する事でXが「As=O」の化合物が得られる。X compound is a compound such as AsCl (NEt 2 ) 2 , AsCl (NiPr 2 ) 2 , AsCl (OEt) 2 , AsCl (OMe) 2 , AsCl 3 , AsBr 3 when X is As (arsenic). Thereafter, a compound of “As = S” is obtained using sulfur (S), LiI, AlCl 3 , AlBr 3 , BF 3 .Et 2 O, and BCl 3 . Furthermore, sulfur (S) can be removed using PBu 3 or P (tBu) 3 and the like, and the target compound of X = As can be obtained. Further, by using hydrogen peroxide, MCPBA or the like as the compound of X = As, a compound of X “As = O” can be obtained.
X compoundは、Xが「C−R1」(炭素)の場合、R1CCl3、R1CBr3、R1CHO、R1COCl、R1COBr、(R1CO)O、R1C(OMe)3、R1C(OEt)3(R1は前記に定義されるとおりである)などの化合物を使用し、その後、AlCl3やAlBr3やBF3・Et2OやBCl3を使用して、目的とするXが「C−R1」の化合物に導くことができる。X compound is R 1 CCl 3 , R 1 CBr 3 , R 1 CHO, R 1 COCl, R 1 COBr, (R 1 CO) O, R 1 C when X is “C—R 1 ” (carbon). A compound such as (OMe) 3 , R 1 C (OEt) 3 (R 1 is as defined above) and then AlCl 3 , AlBr 3 , BF 3 .Et 2 O or BCl 3 Can be used to lead to compounds where the desired X is “C—R 1 ”.
X compoundは、Xが「Si−R1」(ケイ素)の場合、R1SiF3、R1SiCl3、R1SiBr3、R1SiI3、R1Si(OMe)3、R1Si(OEt)3、R1Si(OiPr)3、R1Si(OPh)3(R1は前記に定義されるとおりである)などの化合物を使用し、その後、AlCl3やAlBr3やBF3・Et2OやBCl3を使用して、目的とするXが「Si−R1」の化合物に導くことができる。When X is “Si—R 1 ” (silicon), X compound is R 1 SiF 3 , R 1 SiCl 3 , R 1 SiBr 3 , R 1 SiI 3 , R 1 Si (OMe) 3 , R 1 Si ( OEt) 3 , R 1 Si (OiPr) 3 , R 1 Si (OPh) 3 (R 1 is as defined above) and the like, and then AlCl 3 , AlBr 3 , BF 3. Using Et 2 O or BCl 3 , the target X can be led to a compound having “Si—R 1 ”.
X compoundは、Xが「Si−R1」(ケイ素)の場合、R1SiH2F、R1SiH2Cl、R1SiH2Br、R1SiH2(OMe)、R1SiH2(OEt)、R1SiH2(OiPr)、R1SiH2(OPh) (R1は前記に定義されるとおりである)などの化合物を使用し、その後、Ph3CB(C6F5)4を使用して、目的とするXが「Si−R1」の化合物に導くことができる。X compound is R 1 SiH 2 F, R 1 SiH 2 Cl, R 1 SiH 2 Br, R 1 SiH 2 (OMe), R 1 SiH 2 (OEt) when X is “Si—R 1 ” (silicon). ), R 1 SiH 2 (OiPr), R 1 SiH 2 (OPh) (where R 1 is as defined above), and then Ph 3 CB (C 6 F 5 ) 4 It can be used to lead to compounds where the target X is “Si—R 1 ”.
X compoundは、XがB(ホウ素)の場合、BF3・Et2O、BCl3、BBr3、BI3、B(OMe)3、B(OEt)3、B(OiPr)3、B(OPh)3などの化合物を使用し、その後、AlCl3やAlBr3やBF3・Et2OやBCl3を使用して、目的とするX=Bの化合物に導くことができる。また、X=Bの化合物に「R1−M」(R1とMは前記に定義されるとおりである)を使用する事で、Xが「B−R1・M」の化合物が得られる。When X is B (boron), X compound is BF 3 · Et 2 O, BCl 3 , BBr 3 , BI 3 , B (OMe) 3 , B (OEt) 3 , B (OiPr) 3 , B (OPh) 3 ) can be used, followed by AlCl 3 , AlBr 3 , BF 3 .Et 2 O or BCl 3 to lead to the desired X = B compound. Further, by using “R 1 -M” (R 1 and M are as defined above) for the compound of X = B, a compound in which X is “B—R 1 · M” is obtained. .
X compoundは、Xが「Ge−R1」(ゲルマニウム)の場合、R1GeCl3、R1GeBr3、R1GeI3、R1Ge(OMe)3、R1Ge(OEt)3、R1Ge(OPh)3(R1は前記に定義されるとおりである)などの化合物を使用し、その後、AlCl3やAlBr3やBF3・Et2OやBCl3を使用して、目的とするXが「Ge−R1」の化合物に導くことができる。When X is “Ge—R 1 ” (germanium), X compound is R 1 GeCl 3 , R 1 GeBr 3 , R 1 GeI 3 , R 1 Ge (OMe) 3 , R 1 Ge (OEt) 3 , R 1 Ge (OPh) 3 (R 1 is as defined above) and then using AlCl 3 , AlBr 3 , BF 3 .Et 2 O or BCl 3 X can lead to a compound of “Ge—R 1 ”.
X compoundは、Xが「Sn−R1」(すず)の場合、R1SnCl3、R1SnBr3、R1SnI3、R1Sn(OMe)3、R1Sn(OEt)3、R1Sn(OPh)3(R1は前記に定義されるとおりである)などの化合物を使用し、その後、AlCl3やAlBr3やBF3・Et2OやBCl3を使用して、目的とするXが「Sn−R1」の化合物に導くことができる。When X is “Sn-R 1 ” (tin), X compound is R 1 SnCl 3 , R 1 SnBr 3 , R 1 SnI 3 , R 1 Sn (OMe) 3 , R 1 Sn (OEt) 3 , R 1 Sn (OPh) 3 (R 1 is as defined above) and then using AlCl 3 , AlBr 3 , BF 3 .Et 2 O or BCl 3 X can lead to a compound of “Sn—R 1 ”.
X compoundは、Xが「Sn−R1」(すず)の場合、R1SnH2F、R1SnH2Cl、R1SnH2Br、R1SnH2(OMe)、R1SnH2(OEt)、R1SnH2(OiPr)、R1SnH2(OPh)(R1は前記に定義されるとおりである)などの化合物を使用し、その後、Ph3CB(C6F5)4を使用して、目的とするXが「Sn−R1」の化合物に導くことができる。When X is “Sn—R 1 ” (tin), X compound is R 1 SnH 2 F, R 1 SnH 2 Cl, R 1 SnH 2 Br, R 1 SnH 2 (OMe), R 1 SnH 2 (OEt) ), R 1 SnH 2 (OiPr), R 1 SnH 2 (OPh) (R 1 is as defined above), and then using Ph 3 CB (C 6 F 5 ) 4 It can be used to lead to compounds where the target X is “Sn—R 1 ”.
X compoundは、XがAl(アルミニウム)の場合、AlCl3、AlBr3、AlI3、Al(OMe)3、Al(OEt)3、Al(OiPr)3、Al(OPh)3などの化合物を使用し、その後、AlCl3やAlBr3やBF3・Et2OやBCl3を使用して、目的とするX=Alの化合物に導くことができる。また、X=Alの化合物に「R1-M」(R1とMは前記に定義されるとおりである)を使用する事で、Xが「Al−R1・M」の化合物が得られる。X compound uses a compound such as AlCl 3 , AlBr 3 , AlI 3 , Al (OMe) 3 , Al (OEt) 3 , Al (OiPr) 3 , and Al (OPh) 3 when X is Al (aluminum). Then, using AlCl 3 , AlBr 3 , BF 3 .Et 2 O, and BCl 3 , the target compound of X = Al can be derived. Further, by using “R 1 -M” (where R 1 and M are as defined above) as a compound where X═Al, a compound where X is “Al—R 1 · M” is obtained. .
X compoundは、XがGa(ガリウム)の場合、GaCl3、GaBr3、GaI3、Ga(OMe)3、Ga(OEt)3、Ga(OiPr)3、Ga(OPh)3などの化合物を使用し、その後、AlCl3やAlBr3やBF3・Et2OやBCl3を使用して、目的とするX=Gaの化合物に導くことができる。また、X=Gaの化合物に「R1−M」(R1とMは前記に定義されるとおりである)を使用する事で、Xが「Ga−R1・M」の化合物が得られる。X compound is a compound such as GaCl 3 , GaBr 3 , GaI 3 , Ga (OMe) 3 , Ga (OEt) 3 , Ga (OiPr) 3 , Ga (OPh) 3 when X is Ga (gallium). Thereafter, AlCl 3 , AlBr 3 , BF 3 .Et 2 O, and BCl 3 can be used to lead to the target X = Ga compound. Further, by using “R 1 -M” (where R 1 and M are as defined above) as the compound of X═Ga, a compound in which X is “Ga—R 1 · M” is obtained. .
本発明の化合物は、以下のスキーム2に従い合成することもできる。 The compound of the present invention can also be synthesized according to the following scheme 2.
<スキーム2> <Scheme 2>
式中、I/Brは、IまたはBrを意味し,Br/Clは、BrまたはClを意味する。 In the formula, I / Br means I or Br, and Br / Cl means Br or Cl.
なお、本明細書において、Y1/Y15は、Y1またはY15のいずれかであることを意味し、Y2/Y14、Y3/Y13、Y4/Y12、Y5/Y11、Y6/Y10は、同様にいずれかの基を表す。但し、Y1/Y15がY1を表す場合、Y1と隣接するY2/Y14、Y3/Y13、Y4/Y12、Y5/Y11、Y6/Y10は、各々Y2、Y3、Y4、Y5、Y6を表し、Y1/Y15がY15を表す場合、Y15と隣接するY2/Y14、Y3/Y13、Y4/Y12、Y5/Y11、Y6/Y10は、各々Y14、Y13、Y12、Y11、Y10を表す。従って、式(7)の化合物は、一般式(I)の化合物に含まれる。In the present specification, Y 1 / Y 15 means either Y 1 or Y 15 , and Y 2 / Y 14 , Y 3 / Y 13 , Y 4 / Y 12 , Y 5 / Y 11 and Y 6 / Y 10 similarly represent any group. However, if Y 1 / Y 15 represents Y 1, Y 2 / Y 14 adjacent to Y 1, Y 3 / Y 13 , Y 4 / Y 12, Y 5 / Y 11, Y 6 / Y 10 is each Y 2, Y 3, Y 4 , Y 5, represents Y 6, Y 1 / if Y 15 represents Y 15, Y 2 / Y 14 adjacent to Y 15, Y 3 / Y 13 , Y 4 / Y 12, Y 5 / Y 11 , Y 6 / Y 10 each represents a Y 14, Y 13, Y 12 , Y 11, Y 10. Accordingly, the compound of formula (7) is included in the compound of general formula (I).
式(10)の化合物に、式(11)の化合物と銅粉、塩基及び添加剤を反応させることで、式(12)の化合物に導くことができる。反応は、式(10)の化合物1モルに対し、式(11)の化合物を2モル〜過剰量、銅粉を0.1モル〜3モル程度、塩基を2モル〜過剰量、添加剤を0.05モル〜2モル程度使用し、室温〜溶媒の沸騰する程度の温度下に1〜24時間程度反応させることにより有利に進行する。塩基としてはK2CO3やCs2CO3やAg2CO3やCsOAcやK3PO4を、添加剤としては18−クラウン−6−エーテルやPPh3を、溶媒としては、ウンデカンやドデカンなどの炭化水素系溶媒やキシレンやメシチレン等の芳香族炭化水素系溶媒を使用することができる。The compound of formula (10) can be led to the compound of formula (12) by reacting the compound of formula (11) with copper powder, a base and an additive. In the reaction, 2 mol to excess of the compound of formula (11), about 0.1 mol to 3 mol of copper powder, 2 mol to excess of the base, and additive are added to 1 mol of the compound of formula (10). The reaction proceeds advantageously by using about 0.05 mol to 2 mol and reacting for about 1 to 24 hours at a temperature ranging from room temperature to the boiling point of the solvent. K 2 CO 3 , Cs 2 CO 3 , Ag 2 CO 3 , CsOAc and K 3 PO 4 as bases, 18-crown-6-ether and PPh 3 as additives, undecane and dodecane as solvents, etc. These hydrocarbon solvents and aromatic hydrocarbon solvents such as xylene and mesitylene can be used.
式(12)の化合物とパラジウム触媒と塩基と添加剤を反応させることで目的とする式(7)の化合物を得ることができる。式(12)の化合物1モルに対しパラジウム触媒を0.1モル〜3モル程度、塩基を1モル〜過剰量、添加剤を0.1モル〜3モル程度使用し、溶媒中、室温〜溶媒の沸騰する程度の温度下に30分〜24時間反応させることにより目的とする式(9)の化合物を得ることができる。パラジウム触媒としてはPd(OAc)2やPdCl2やPd2(dba)3を、塩基としてはK2CO3やCs2CO3やAg2CO3やCsOAcやK3PO4を、添加剤としてはBu4NBrやPPh3やPtBu2MeやPCy3やP(t-Bu)3やS-PhosやdppfやXantphosを、溶媒としては無水DMFや無水DMAなどの無水アミド系溶媒やキシレンやメシチレン等の芳香族炭化水素系溶媒を使用することができる。The target compound of formula (7) can be obtained by reacting the compound of formula (12), palladium catalyst, base and additive. The palladium catalyst is used in an amount of about 0.1 mol to 3 mol, the base is used in an amount of 1 mol to an excess, and the additive is used in an amount of about 0.1 mol to 3 mol with respect to 1 mol of the compound of formula (12). The desired compound of the formula (9) can be obtained by reacting for 30 minutes to 24 hours at a temperature of about the boiling point. Pd (OAc) 2 or PdCl 2 or Pd 2 (dba) 3 as a palladium catalyst, K 2 CO 3 or Cs 2 CO 3 or Ag 2 CO 3 or CsOAc or K 3 PO 4 as an additive as a base Is Bu 4 NBr, PPh 3 , PtBu 2 Me, PCy 3 , P (t-Bu) 3 , S-Phos, dppf and Xantphos, and the solvent is anhydrous amide solvents such as anhydrous DMF and anhydrous DMA, xylene and mesitylene. Aromatic hydrocarbon solvents such as can be used.
式(12)の化合物は、以下のスキーム3に従い合成することもできる。 The compound of the formula (12) can also be synthesized according to the following scheme 3.
<スキーム3> <Scheme 3>
式(13)の化合物に、式(14)の化合物を反応させることで、式(12)の化合物に導くことができる。反応は、式(13)の化合物1モルに対し、式(14)の化合物を2モル〜過剰量使用し、−78℃〜溶媒の沸騰する程度の温度下に1〜24時間程度反応させることにより有利に進行する。溶媒としては、無水THFの無水エーテル系溶媒を使用することができる。 By reacting the compound of the formula (13) with the compound of the formula (14), the compound of the formula (12) can be led. In the reaction, 2 mol to an excess amount of the compound of formula (14) is used with respect to 1 mol of the compound of formula (13), and the reaction is performed at a temperature of about -78 ° C. to boiling of the solvent for about 1 to 24 hours. Proceed more advantageously. As the solvent, an anhydrous ether solvent of anhydrous THF can be used.
本発明の化合物は、以下のスキーム4に従い合成することもできる。 The compound of the present invention can also be synthesized according to the following scheme 4.
<スキーム4> <Scheme 4>
反応は、式(15)の化合物1モルに対し、式(2)の化合物を6モル〜過剰量使用し、溶媒中−78℃〜溶媒の沸騰する程度の温度下に30分〜24時間撹拌し、その後、その溶液にI2あるいはN-ブロモスクシンイミド(NBS)を2モル〜過剰量加えることで、目的とする式(16)の化合物を得ることができる。溶媒としては、無水THF、無水アニソールなどの無水エーテル系溶媒やクロロベンゼン、ジクロロベンゼンなどのハロゲン化芳香族炭化水素溶媒が用いられる。In the reaction, 6 mol to an excess amount of the compound of formula (2) is used with respect to 1 mol of the compound of formula (15), and the mixture is stirred for 30 minutes to 24 hours in a solvent at −78 ° C. to a temperature at which the solvent boils. Then, by adding 2 mol to an excess of I 2 or N-bromosuccinimide (NBS) to the solution, the target compound of the formula (16) can be obtained. As the solvent, anhydrous ether solvents such as anhydrous THF and anhydrous anisole, and halogenated aromatic hydrocarbon solvents such as chlorobenzene and dichlorobenzene are used.
式(16)の化合物に対し、溶媒中n-BuLiあるいはt-BuLiとXcompoundを加え、−78℃〜溶媒の沸騰する程度の温度下に30分〜24時間反応させることにより目的とする式(17)の化合物を得ることができる。溶媒としては、ベンゼン、トルエン、キシレン、メシチレンなどの芳香族炭化水素系溶媒、またはクロロベンゼン、ジクロロベンゼンなどのハロゲン化芳香族炭化水素溶媒が用いられる。反応は式(16)の化合物1モルに対しn-BuLiを2モル〜過剰量あるいはt-BuLiを4モル〜過剰量使用して式(16)の化合物の2つのI(ヨウ素)基あるいはBr(臭素)基を引き抜き、次いでX compoundを2モル〜過剰量加え、スキーム1の化合物(7), (8)または(9)の製造法と同様に処理することで、式(17)の化合物を得る。 To the compound of formula (16), n-BuLi or t-BuLi and Xcompound are added in a solvent, and the reaction is carried out for 30 minutes to 24 hours at a temperature of about -78 ° C to the boiling point of the solvent. The compound of 17) can be obtained. As the solvent, aromatic hydrocarbon solvents such as benzene, toluene, xylene and mesitylene, or halogenated aromatic hydrocarbon solvents such as chlorobenzene and dichlorobenzene are used. The reaction is carried out using 2 mol-excess of n-BuLi or 4 mol-excess of t-BuLi to 1 mol of the compound of formula (16). The compound of the formula (17) is obtained by extracting the (bromine) group and then adding 2 mol to an excess amount of X compound and treating in the same manner as in the production method of the compound (7), (8) or (9) of Scheme 1. Get.
本発明の化合物は、以下のスキーム5に従い合成することもできる。 The compound of the present invention can also be synthesized according to the following scheme 5.
<スキーム5> <Scheme 5>
式(15’)の化合物に、式(18)の化合物とパラジウム触媒、塩基及び添加剤を反応させることで、式(19)の化合物に導くことができる。反応は、式(15’)の化合物1モルに対し、式(18)の化合物を3モル〜過剰量、パラジウム触媒を0.03モル〜0.5モル程度、塩基を3モル〜過剰量、添加剤を0.03モル〜0.5モル程度使用し、0℃〜溶媒の沸騰する程度の温度下に1〜24時間程度反応させることにより有利に進行する。パラジウム触媒としてはPd(OAc)2やPdCl2やPd2(dba)3を、塩基としてはKFやK2CO3やCs2CO3やAg2CO3やCsOAcやK3PO4を、添加剤としてはPPh3やPCy3やP(t-Bu)3やS-PhosやdppfやXantphosを、溶媒としては、THF、ジオキサン、アニソールなどのエーテル系溶媒やトルエンやキシレン等の芳香族炭化水素系溶媒あるいはそれら有機溶媒と水との混合溶媒を使用することができる。By reacting the compound of the formula (15 ′) with the compound of the formula (18), a palladium catalyst, a base, and an additive, the compound of the formula (19) can be derived. In the reaction, 3 mol to excess of the compound of formula (18), about 0.03 mol to 0.5 mol of palladium catalyst, 3 mol to excess of base, and 1 mol of compound of formula (15 ′) The process proceeds advantageously by using the additive in an amount of about 0.03 to 0.5 mol and reacting at a temperature of about 0 ° C. to the boiling of the solvent for about 1 to 24 hours. Pd (OAc) 2 or PdCl 2 or Pd 2 (dba) 3 is added as a palladium catalyst, and KF, K 2 CO 3 , Cs 2 CO 3 , Ag 2 CO 3 , CsOAc or K 3 PO 4 is added as a base the PPh 3 or PCy 3 and P (t-Bu) 3 and S-Phos and dppf and Xantphos as agent, as a solvent, THF, dioxane, aromatic hydrocarbons such as ethereal solvents, toluene, xylene, such as anisole A system solvent or a mixed solvent of these organic solvents and water can be used.
式(19)の化合物に対し、溶媒中n-BuLiあるいはt-BuLiとXcompoundを加え、−78℃〜溶媒の沸騰する程度の温度下に30分〜24時間反応させることにより目的とする式(20)の化合物を得ることができる。溶媒としては、ベンゼン、トルエン、キシレン、メシチレンなどの芳香族炭化水素系溶媒、またはクロロベンゼン、ジクロロベンゼンなどのハロゲン化芳香族系溶媒が用いられる。反応は式(16)の化合物1モルに対しn-BuLiを3モル〜過剰量あるいはt-BuLiを6モル〜過剰量使用して式(17)の化合物の3つのBr(臭素)基を引き抜き、次いでX compoundを3モル〜過剰量加え、スキーム1の化合物(7), (8)または(9)の製造法と同様に処理することで、式(17)の化合物を得る。 To the compound of formula (19), n-BuLi or t-BuLi and Xcompound are added in a solvent, and the reaction is carried out for 30 minutes to 24 hours at a temperature from -78 ° C to the boiling point of the solvent. The compound of 20) can be obtained. As the solvent, aromatic hydrocarbon solvents such as benzene, toluene, xylene and mesitylene, or halogenated aromatic solvents such as chlorobenzene and dichlorobenzene are used. The reaction uses 3 moles to excess of n-BuLi or 6 moles to excess of t-BuLi per mole of the compound of formula (16) to extract the three Br (bromine) groups of the compound of formula (17). Then, X compound is added in an amount of 3 mol to an excess amount, and treated in the same manner as in the production method of compound (7), (8) or (9) in Scheme 1, to obtain the compound of formula (17).
次に、有機発光素子について詳細に説明する。 Next, the organic light emitting device will be described in detail.
本発明の有機発光素子は、陽極及び陰極からなる少なくとも一対の電極と、該一対の電極間に挟持された少なくとも一層の有機化合物からなる層からなる有機発光素子において、前記有機化合物を含む層の少なくとも一層が一般式(I)で示される化合物の少なくとも一種を含有することを特徴とする。 The organic light-emitting device of the present invention is an organic light-emitting device comprising at least a pair of electrodes comprising an anode and a cathode, and a layer comprising at least one organic compound sandwiched between the pair of electrodes. At least one layer contains at least one compound represented by the general formula (I).
本発明の有機発光素子は、有機化合物を含む層のうち、少なくとも発光層が、前記化合物の少なくとも一種を含有することが好ましい。また、発光層がホストとゲストの2つ以上の化合物からなる有機発光素子において、該ホストまたはゲストが前記化合物であることが好ましい。なお、本発明におけるゲストとは、有機EL素子の発光領域において、正孔と電子の再結合に応答して光を発する化合物のことであり、発光領域を形成する物質(ホスト)に含有させるものである。 In the organic light-emitting device of the present invention, it is preferable that at least a light-emitting layer among the layers containing an organic compound contains at least one of the compounds. In the organic light-emitting device in which the light-emitting layer is composed of two or more compounds of a host and a guest, the host or guest is preferably the compound. The guest in the present invention is a compound that emits light in response to recombination of holes and electrons in the light emitting region of the organic EL element, and is included in the substance (host) that forms the light emitting region. It is.
本発明に係る前記一般式(I)で表される化合物を、ゲストとして用いる場合の含有量としては、50重量%以下であることが好ましく、更に好ましくは、0.1重量%以上30重量%以下であり、特に好ましくは、0.1重量%以上15重量%以下である。 When the compound represented by the general formula (I) according to the present invention is used as a guest, the content is preferably 50% by weight or less, more preferably from 0.1% by weight to 30% by weight. Or less, and particularly preferably 0.1 wt% or more and 15 wt% or less.
一方、本発明に関わる前記一般式(I)で表される化合物をホスト化合物として用いる場合、ゲストに特に制限は無く、所望する発光色等によって、後述する化合物等を適宜用いることが出来る。また、必要に応じてゲスト以外に、ホール輸送性化合物、電子輸送性化合物などを一緒にドープして使用することもできる。 On the other hand, when the compound represented by the general formula (I) according to the present invention is used as a host compound, the guest is not particularly limited, and the compounds described below can be appropriately used depending on the desired emission color. In addition to the guest, if necessary, a hole transporting compound, an electron transporting compound, etc. can be doped together and used.
有機化合物層として発光層のみに本発明の化合物を用いてもよいが、必要に応じ、発光層以外に、例えば正孔注入層、正孔輸送層、電子注入層、電子輸送層、電子障壁層なども用いることができる。 The compound of the present invention may be used only in the light emitting layer as the organic compound layer, but if necessary, other than the light emitting layer, for example, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron barrier layer Etc. can also be used.
本発明の有機発光素子においては、上記一般式(I)で示される化合物を真空蒸着法や溶液塗布法により陽極及び陰極の間に形成する。その有機層の厚みは10μmより薄く、好ましくは0.5μm以下、より好ましくは0.01以上0.5μm以下の厚みに薄膜化することが好ましい。 In the organic light emitting device of the present invention, the compound represented by the general formula (I) is formed between the anode and the cathode by a vacuum deposition method or a solution coating method. The thickness of the organic layer is thinner than 10 μm, preferably 0.5 μm or less, more preferably 0.01 to 0.5 μm.
本発明の有機発光素子において、一般式(I)で示される化合物を含有する層および他の有機化合物を含有する層は、一般には真空蒸着法あるいは、適当な溶媒に溶解させて塗布法により薄膜を形成する。特に塗布法で成膜する場合は、適当な結着樹脂と組み合わせて膜を形成することもできる。 In the organic light-emitting device of the present invention, the layer containing the compound represented by the general formula (I) and the layer containing another organic compound are generally formed into a thin film by a vacuum deposition method or a coating method by dissolving in an appropriate solvent. Form. In particular, when a film is formed by a coating method, the film can be formed in combination with an appropriate binder resin.
上記結着樹脂としては広範囲な結着性樹脂より選択でき、たとえばポリビニルカルバゾール樹脂、ポリカーボネート樹脂、ポリエステル樹脂、ポリアリレート樹脂、ポリスチレン樹脂、アクリル樹脂、メタクリル樹脂、ブチラール樹脂、ポリビニルアセタール樹脂、ジアリルフタレート樹脂、フェノール樹脂、エポキシ樹脂、シリコーン樹脂、ポリスルホン樹脂、尿素樹脂等が挙げられるが、これらに限定されるものではない。また、これらは単独または共重合体ポリマーとして1種または2種以上混合してもよい。 The binder resin can be selected from a wide range of binder resins such as polyvinyl carbazole resin, polycarbonate resin, polyester resin, polyarylate resin, polystyrene resin, acrylic resin, methacrylic resin, butyral resin, polyvinyl acetal resin, diallyl phthalate resin. , Phenol resin, epoxy resin, silicone resin, polysulfone resin, urea resin and the like, but are not limited thereto. Moreover, you may mix these 1 type, or 2 or more types as a single or copolymer polymer.
陽極材料としては例えば、金、白金、ニッケル、パラジウム、コバルト、セレン、バナジウム等の金属単体あるいはこれらの合金、酸化錫、酸化亜鉛、酸化錫インジウム(ITO)、酸化亜鉛インジウム等の金属酸化物が使用できる。また、ポリアニリン、ポリピロール、ポリチオフェン、ポリフェニレンスルフィド等の導電性ポリマーも使用できる。これらの電極物質は単独で用いてもよく、複数併用することもできる。 Examples of anode materials include simple metals such as gold, platinum, nickel, palladium, cobalt, selenium, and vanadium or alloys thereof, tin oxide, zinc oxide, indium tin oxide (ITO), and metal oxides such as indium zinc oxide. Can be used. In addition, conductive polymers such as polyaniline, polypyrrole, polythiophene, and polyphenylene sulfide can also be used. These electrode materials may be used alone or in combination.
陰極材料としては例えば、リチウム、ナトリウム、カリウム、セシウム、カルシウム、マグネシウム、アルミニウム、インジウム、銀、鉛、錫、クロム等の金属単体あるいは複数の合金として用いることができる。酸化錫インジウム(ITO)等の金属酸化の利用も可能である。また、陰極は一層構成でもよく、多層構成をとることもできる。 As the cathode material, for example, a single metal such as lithium, sodium, potassium, cesium, calcium, magnesium, aluminum, indium, silver, lead, tin, chromium, or a plurality of alloys can be used. It is also possible to use metal oxidation such as indium tin oxide (ITO). Further, the cathode may have a single layer structure or a multilayer structure.
本発明で用いる基板としては、特に限定するものではないが、金属製基板、セラミックス製基板等の不透明性基板、ガラス、石英、プラスチックシート等の透明性基板が用いられる。また、基板にカラーフィルター膜、蛍光色変換フィルター膜、誘電体反射膜などを用いて発色光をコントロールする事も可能である。 Although it does not specifically limit as a board | substrate used by this invention, Transparent substrates, such as opaque board | substrates, such as a metal board | substrate and a ceramic board | substrate, glass, quartz, a plastic sheet, are used. It is also possible to control the color light by using a color filter film, a fluorescent color conversion filter film, a dielectric reflection film, or the like on the substrate.
なお、作成した素子に対して、酸素や水分等との接触を防止する目的で保護層あるいは封止層を設けることもできる。保護層としては、ダイヤモンド薄膜、金属酸化物、金属窒化物等の無機材料膜、フッソ樹脂、ポリパラキシレン、ポリエチレン、シリコーン樹脂、ポリスチレン樹脂等の高分子膜さらには、光硬化性樹脂等が挙げられる。また、ガラス、気体不透過性フィルム、金属などをカバーし、適当な封止樹脂により素子自体をパッケージングすることもできる。 Note that a protective layer or a sealing layer can be provided on the prepared element for the purpose of preventing contact with oxygen or moisture. Examples of protective layers include diamond thin films, inorganic material films such as metal oxides and metal nitrides, polymer films such as fluorine resin, polyparaxylene, polyethylene, silicone resin, polystyrene resin, and photo-curing resins. It is done. Further, it is possible to cover glass, a gas impermeable film, a metal, etc., and to package the element itself with an appropriate sealing resin.
以下、実施例により本発明をさらに具体的に説明していくが、本発明はこれらに限定されるものではない。
実施例1
1,1’−(2−ヨード−1,3−フェニレン)ビス(2−メチルナフタレン)
合成例1:EXAMPLES Hereinafter, the present invention will be described more specifically with reference to examples, but the present invention is not limited to these examples.
Example 1
1,1 ′-(2-iodo-1,3-phenylene) bis (2-methylnaphthalene)
Synthesis example 1:
1,3−ジクロロベンゼン(7.35g、50.0mmol)及びTHF(70mL)に、アルゴン雰囲気下−78℃で、ブチルリチウムのヘキサン溶液(30.5mL、1.64M、50.0mmol)を添加し撹拌した。2時間後、ヨウ素のTHF溶液(30.0mL、1.67M、50.0mmol)を加えた後、室温下、チオ硫酸ナトリウム飽和水溶液100mLを加え、有機層を回収し、水層をジエチルエーテルを用いて3回抽出した。合わせた有機抽出物に含まれる水分を硫酸マグネシウムで除去し、濾過した。溶媒を減圧下に留去した後、得られた白色の油状物質にメタノールを用いてトリチュレーションすることで白色結晶を生成させ、白色粉末として1,3−ジクロロ−2−ヨードベンゼンを得た(11.75g、収率86%)。得られた1,3−ジクロロ−2−ヨードベンゼン(5.46g、20.0mmol)に、アルゴン雰囲気下0℃で(2−メチルナフタレン−1−イル)マグネシウムブロミドのTHF溶液(93.0mL、0.86M、80.0mmol)を添加し室温で1時間撹拌した後、80℃に昇温した。14時間後、0℃でヨウ素のTHF溶液(60.0mL、1.67M、100mmol)を加えた後、室温下、チオ硫酸ナトリウム飽和水溶液100mLを加え、有機層を回収し、水層をジエチルエーテルを用いて3回抽出した。合わせた有機抽出物に含まれる水分を硫酸マグネシウムで除去し、濾過した。溶媒を減圧下に留去した後、得られた褐色の油状物質にヘキサンを用いてトリチュレーションすることで、白褐色粉末として標題化合物を得た(3.03g、収率31%)。
1H NMR (δppm in CDCl3); 2.25(s, 6H), 7.24-7.45(m, 10H), 7.61(t, 1H, J = 7.4 Hz), 7.83-7.88(m, 4H);13C NMR (δppm in CDCl3); 20.5(2C), 124.9, 125.0, 125.3, 125.4, 126.1, 126.2, 127.8, 127.9, 128.5, 128.6, 128.7, 129.2, 132.0, 132.1, 133.1, 140.9, 146.0
合成例2:To 1,3-dichlorobenzene (7.35 g, 50.0 mmol) and THF (70 mL) was added a hexane solution of butyllithium (30.5 mL, 1.64 M, 50.0 mmol) at −78 ° C. under an argon atmosphere. And stirred. After 2 hours, a solution of iodine in THF (30.0 mL, 1.67 M, 50.0 mmol) was added, and then 100 mL of a saturated aqueous solution of sodium thiosulfate was added at room temperature. The organic layer was recovered, and the aqueous layer was diluted with diethyl ether. And extracted 3 times. Water contained in the combined organic extracts was removed with magnesium sulfate and filtered. After the solvent was distilled off under reduced pressure, white crystals were produced by triturating the obtained white oily substance with methanol to obtain 1,3-dichloro-2-iodobenzene as a white powder. (11.75 g, 86% yield). To the obtained 1,3-dichloro-2-iodobenzene (5.46 g, 20.0 mmol), a THF solution (93.0 mL, (2-methylnaphthalen-1-yl) magnesium bromide) was added at 0 ° C. under an argon atmosphere. 0.86M, 80.0 mmol) was added, and the mixture was stirred at room temperature for 1 hour, and then heated to 80 ° C. After 14 hours, a THF solution of iodine (60.0 mL, 1.67 M, 100 mmol) was added at 0 ° C., and then 100 mL of a saturated aqueous solution of sodium thiosulfate was added at room temperature, the organic layer was recovered, and the aqueous layer was diluted with diethyl ether. Extracted three times using. Water contained in the combined organic extracts was removed with magnesium sulfate and filtered. After distilling off the solvent under reduced pressure, the resulting brown oil was triturated with hexane to give the title compound as a white brown powder (3.03 g, 31% yield).
1 H NMR (δppm in CDCl 3 ); 2.25 (s, 6H), 7.24-7.45 (m, 10H), 7.61 (t, 1H, J = 7.4 Hz), 7.83-7.88 (m, 4H); 13 C NMR (δppm in CDCl 3 ); 20.5 (2C), 124.9, 125.0, 125.3, 125.4, 126.1, 126.2, 127.8, 127.9, 128.5, 128.6, 128.7, 129.2, 132.0, 132.1, 133.1, 140.9, 146.0
Synthesis example 2:
1,3−ジクロロベンゼン(4.41g、30mmol)及びTHF(40mL)に、アルゴン雰囲気下,−78℃で、ブチルリチウムのヘキサン溶液(18.3mL、1.64M、30.0mmol)を添加し撹拌した。2時間後、0℃で(2−メチルナフタレン−1−イル)マグネシウムブロミドのTHF溶液(69.8mL、0.86M、60.0mmol)を添加し室温で1時間撹拌した後、80℃に昇温した。14時間後、0℃でヨウ素のTHF溶液(19.8mL、1.67M、33.0mmol)を加えた後、室温下、チオ硫酸ナトリウム飽和水溶液100mLを加え、有機層を回収し、水層をジエチルエーテルを用いて3回抽出した。合わせた有機抽出物に含まれる水分を硫酸マグネシウムで除去し、濾過した。溶媒を減圧下に留去した後、得られた褐色の油状物質にヘキサンを用いてトリチュレーションすることで、白褐色粉末として標題化合物を得た(4.65g、収率32%)。 To 1,3-dichlorobenzene (4.41 g, 30 mmol) and THF (40 mL) was added hexane solution of butyllithium (18.3 mL, 1.64 M, 30.0 mmol) at −78 ° C. under argon atmosphere. Stir. After 2 hours, a THF solution (69.8 mL, 0.86 M, 60.0 mmol) of (2-methylnaphthalen-1-yl) magnesium bromide was added at 0 ° C., and the mixture was stirred at room temperature for 1 hour and then raised to 80 ° C. Warm up. After 14 hours, a THF solution of iodine (19.8 mL, 1.67 M, 33.0 mmol) was added at 0 ° C., and then 100 mL of a saturated aqueous solution of sodium thiosulfate was added at room temperature. The organic layer was recovered, and the aqueous layer was collected. Extract three times with diethyl ether. Water contained in the combined organic extracts was removed with magnesium sulfate and filtered. After distilling off the solvent under reduced pressure, the resulting brown oily substance was triturated with hexane to obtain the title compound as a white brown powder (4.65 g, yield 32%).
実施例2
2,6−ビス(2ーメチルナフタレン−1−イル)ビス(ジエチルアミノ)ホスフィンExample 2
2,6-Bis (2-methylnaphthalen-1-yl) bis (diethylamino) phosphine
1,1’−(2−ヨード−1,3−フェニレン)ビス(2−メチルナフタレン)(7.27g、15.0mmol)及びトルエン(75mL)に、アルゴン雰囲気下−78℃で、t−ブチルリチウムのペンタン溶液(19.0mL、1.58M、30.0mmol)を添加し撹拌した。1時間後0℃に昇温しさらに1時間撹拌した後、−78℃でビス(ジエチルアミノ)クロロホスフィンのTHF溶液(11.3mL、2.0M、22.5mmol)を添加した。3時間後、室温にした反応溶液にヘキサンを加え濾過した後、溶媒を減圧下に留去し、得られた朱色の油状物質にメタノールを用いてトリチュレーションすることで、白褐色粉末として標題化合物を得た(5.42g、収率68%)。 To 1,1 ′-(2-iodo-1,3-phenylene) bis (2-methylnaphthalene) (7.27 g, 15.0 mmol) and toluene (75 mL) at −78 ° C. under argon atmosphere at t-butyl Lithium pentane solution (19.0 mL, 1.58 M, 30.0 mmol) was added and stirred. After 1 hour, the temperature was raised to 0 ° C. and the mixture was further stirred for 1 hour, and then a solution of bis (diethylamino) chlorophosphine in THF (11.3 mL, 2.0 M, 22.5 mmol) was added at −78 ° C. After 3 hours, hexane was added to the reaction solution brought to room temperature and filtered, and then the solvent was distilled off under reduced pressure. The obtained vermilion oily substance was triturated with methanol to give the title as a white brown powder. The compound was obtained (5.42 g, yield 68%).
実施例3
2,6−ビス(2−メチルナフタレン−1−イル)ビス(ジエチルアミノ)ホスフィンスルフィドExample 3
2,6-bis (2-methylnaphthalen-1-yl) bis (diethylamino) phosphine sulfide
2,6−ビス(2−メチルナフタレン−1−イル)ビス(ジエチルアミノ)ホスフィン(5.33g、10.0mmol)及び硫黄(0.481g、15.0mmol)にアルゴン雰囲気下室温で、ベンゼン(40mL)を加え1時間撹拌した。溶媒を減圧下に留去し、得られた白色固体をメタノールで洗浄することで、白色粉末として標題化合物を得た(5.23g、収率93%)。
1H NMR (δppm in C6D6); 0.39(t, 6H, J = 6.9 Hz), 0.67(t, 6H, J = 6.9 Hz), 1.73-1.91(m, 2H), 2.17-2.34(m, 2H), 2.45-2.59(m, 2H), 2.52(s, 6H), 2.70-2.88(m, 2H), 6.88(dd, 2H, J = 4.1, 7.3 Hz), 7.01-7.07(m, 1H), 7.22-7.28(m, 6H), 7.60-7.77(m, 6H); 31P NMR (δppm in C6D6); 69.12,6-bis (2-methylnaphthalen-1-yl) bis (diethylamino) phosphine (5.33 g, 10.0 mmol) and sulfur (0.481 g, 15.0 mmol) in benzene (40 mL) at room temperature under an argon atmosphere. ) Was added and stirred for 1 hour. The solvent was distilled off under reduced pressure, and the resulting white solid was washed with methanol to give the title compound as a white powder (5.23 g, yield 93%).
1 H NMR (δppm in C 6 D 6 ); 0.39 (t, 6H, J = 6.9 Hz), 0.67 (t, 6H, J = 6.9 Hz), 1.73-1.91 (m, 2H), 2.17-2.34 (m , 2H), 2.45-2.59 (m, 2H), 2.52 (s, 6H), 2.70-2.88 (m, 2H), 6.88 (dd, 2H, J = 4.1, 7.3 Hz), 7.01-7.07 (m, 1H ), 7.22-7.28 (m, 6H), 7.60-7.77 (m, 6H); 31 P NMR (δppm in C 6 D 6 ); 69.1
実施例4
6,10−ジメチル−15b−チオホスファナフト[1,8−ab]ペリレン
合成例1:Example 4
6,10-Dimethyl-15b-thiophosphanaphtho [1,8-ab] perylene Synthesis Example 1:
2,6−ビス(2−メチルナフタレン−1−イル)ビス(ジエチルアミノ)ホスフィンスルフィド(2.26g、4.00mmol)及び三塩化アルミニウム(2.13g、16.0mmol)にアルゴン雰囲気下室温で、1,2−ジクロロベンゼン(40mL)を加え、120℃で14時間撹拌した。トリエチルアミン(16mL)を加えた後、溶媒を減圧下加熱して留去し、濾過して得られた粗生成物をシリカゲルカラムクロマトグラフィー(溶媒:トルエン、ジクロロメタン)により単離することで黄色粉末として標題化合物を得た(0.957g、収率57%)。
HRMS(EI) m/z; calcd. 418.0945[M]+; found 418.0946
1H NMR (δppm in CD2Cl2); 2.98(s, 6H), 7.52-7.75(m, 7H), 7.88(dd, 2H, J= 2.0, 8.1 Hz), 8.05(d, 2H, J = 8.1 Hz), 8.58(dd, 2H, J = 7.3, 13.5 Hz);13C NMR (δppm in CD2Cl2); 24.3(2C), 125.7, 125.9, 128.3, 129.1(2C), 129.8(2C), 130.5, 130.9(2C), 131.0, 131.1, 131.2, 131.8, 131.9, 132.2(2C), 132.3, 136.7(2C), 138.7(2C); 31P NMR (δppm in CD2Cl2);-8.1
X-ray crystal structure of 42,6-bis (2-methylnaphthalen-1-yl) bis (diethylamino) phosphine sulfide (2.26 g, 4.00 mmol) and aluminum trichloride (2.13 g, 16.0 mmol) at room temperature under argon atmosphere, 1,2-Dichlorobenzene (40 mL) was added and stirred at 120 ° C. for 14 hours. After adding triethylamine (16 mL), the solvent is distilled off by heating under reduced pressure, and the crude product obtained by filtration is isolated as a yellow powder by silica gel column chromatography (solvent: toluene, dichloromethane). The title compound was obtained (0.957 g, 57% yield).
HRMS (EI) m / z; calcd. 418.0945 [M] + ; found 418.0946
1 H NMR (δppm in CD 2 Cl 2 ); 2.98 (s, 6H), 7.52-7.75 (m, 7H), 7.88 (dd, 2H, J = 2.0, 8.1 Hz), 8.05 (d, 2H, J = 8.1 Hz), 8.58 (dd, 2H, J = 7.3, 13.5 Hz); 13 C NMR (δppm in CD 2 Cl 2 ); 24.3 (2C), 125.7, 125.9, 128.3, 129.1 (2C), 129.8 (2C) , 130.5, 130.9 (2C), 131.0, 131.1, 131.2, 131.8, 131.9, 132.2 (2C), 132.3, 136.7 (2C), 138.7 (2C); 31 P NMR (δppm in CD 2 Cl 2 ); -8.1
X-ray crystal structure of 4
合成例2: Synthesis example 2:
1,1’−(2−ヨード−1,3−フェニレン)ビス(2−メチルナフタレン)(0.484g、1.00mmol)及びトルエン(5.0mL)にアルゴン雰囲気下−78℃で、t−ブチルリチウムのペンタン溶液(1.28mL、1.56M、2.00mmol)を添加し撹拌した。1時間後0℃に昇温しさらに1時間撹拌した後、−78℃で三塩化リン(0.137g、1.00mmol)を加え、3時間撹拌した。溶媒を減圧下留去し、1,2−ジクロロベンゼン(10mL)を加えた後、三塩化アルミニウム(0.533g、4.00mmol)及び硫黄(0.048g、1.50mmol)を添加し、120℃で14時間撹拌した。トリエチルアミン(4.0mL)を加えた後、溶媒を減圧下加熱して留去し、濾過して得られた粗生成物をシリカゲルカラムクロマトグラフィー(溶媒:トルエン、ジクロロメタン)により単離することで黄色粉末として標題化合物を得た(0.230g、収率55%)。 1,1 ′-(2-iodo-1,3-phenylene) bis (2-methylnaphthalene) (0.484 g, 1.00 mmol) and toluene (5.0 mL) at −78 ° C. under argon atmosphere at t− A solution of butyllithium in pentane (1.28 mL, 1.56 M, 2.00 mmol) was added and stirred. After 1 hour, the temperature was raised to 0 ° C. and the mixture was further stirred for 1 hour, and phosphorus trichloride (0.137 g, 1.00 mmol) was added at −78 ° C., followed by stirring for 3 hours. The solvent was distilled off under reduced pressure, 1,2-dichlorobenzene (10 mL) was added, and then aluminum trichloride (0.533 g, 4.00 mmol) and sulfur (0.048 g, 1.50 mmol) were added. Stir at 14 ° C. for 14 hours. After adding triethylamine (4.0 mL), the solvent is distilled off by heating under reduced pressure, and the crude product obtained by filtration is isolated by silica gel column chromatography (solvent: toluene, dichloromethane) to give a yellow color. The title compound was obtained as a powder (0.230 g, 55% yield).
実施例5
6,10−ジメチル−15b−ホスファナフト[1,8−ab]ペリレンExample 5
6,10-Dimethyl-15b-phosphanaphtho [1,8-ab] perylene
6,10−ジメチル−15b−チオホスファナフト[1,8−ab]ペリレン(0.418g、1.00mmol)及びトリブチルホスフィン(0.303g、1.50mmol)にアルゴン雰囲気下0℃で、1,2−ジクロロベンゼン(20mL)を加え120℃で18時間撹拌した。溶媒を減圧下留去しヘキサンを加えトリチュレーションすることで、黄色粉末として標題化合物を得た(0.373g、収率97%)。
HRMS(EI) m/z; calcd. 386.1224[M]+; found 386.1222
1H NMR (δppm in CD2Cl2); 2.85(s, 6H), 7.36-7.57(m, 7H), 7.76(dd, 4H, J = 2.3, 8.2 Hz), 8.15(t, 2H, J = 6.8 Hz); 13C NMR δ ppm in CD2Cl2; 23.6(2C), 125.3(2C), 127.2, 127.4(2C), 127.5, 127.9, 128.6(2C), 129.9(2C), 130.2, 130.6, 130.8, 131.6(2C), 132.9(2C), 133.6(2C), 133.7(2C), 135.4(2C), 135.6(2C); 31P NMR (δppm in CD2Cl2); -44.66,10-dimethyl-15b-thiophosphanaphtho [1,8-ab] perylene (0.418 g, 1.00 mmol) and tributylphosphine (0.303 g, 1.50 mmol) at 0 ° C. under an argon atmosphere at 1 ° C. , 2-dichlorobenzene (20 mL) was added and stirred at 120 ° C. for 18 hours. The solvent was distilled off under reduced pressure, and hexane was added to perform trituration to obtain the title compound as a yellow powder (0.373 g, yield 97%).
HRMS (EI) m / z; calcd. 386.1224 [M] + ; found 386.1222
1 H NMR (δppm in CD 2 Cl 2 ); 2.85 (s, 6H), 7.36-7.57 (m, 7H), 7.76 (dd, 4H, J = 2.3, 8.2 Hz), 8.15 (t, 2H, J = 6.8 Hz); 13 C NMR δ ppm in CD 2 Cl 2 ; 23.6 (2C), 125.3 (2C), 127.2, 127.4 (2C), 127.5, 127.9, 128.6 (2C), 129.9 (2C), 130.2, 130.6, 130.8, 131.6 (2C), 132.9 (2C), 133.6 (2C), 133.7 (2C), 135.4 (2C), 135.6 (2C); 31 P NMR (δppm in CD 2 Cl 2 ); -44.6
実施例6
6,10−ジメチル−15b−オキサホスファナフト[1,8−ab]ペリレンExample 6
6,10-Dimethyl-15b-oxaphosphanaphtho [1,8-ab] perylene
6,10−ジメチル−15b−ホスファナフト[1,8−ab]ペリレン(0.077g、0.20mmol)及びジクロロメタン(2.0mL)に対し30%過酸化水素水(2.0mL)を添加し、室温で6時間攪拌した。抽出した有機層の溶媒を減圧下留去し、得られた粗生成物をシリカゲルカラムクロマトグラフィー(溶媒:ジクロロメタン、酢酸エチル)により単離することで淡黄色粉末として標題化合物を得た(0.057g、収率71%)。
HRMS(EI) calcd for C28H20PO ([M+H]+):403.1252, observed 403.1245.
31P NMR (CD-2Cl2, 160 MHz) δ -10.6.
UV-vis and Fluorescence in CH2Cl2: λabs = 379 nm, λem = 415 nm, Φf = 0.8330% aqueous hydrogen peroxide (2.0 mL) was added to 6,10-dimethyl-15b-phosphanaft [1,8-ab] perylene (0.077 g, 0.20 mmol) and dichloromethane (2.0 mL), Stir at room temperature for 6 hours. The solvent of the extracted organic layer was distilled off under reduced pressure, and the resulting crude product was isolated by silica gel column chromatography (solvent: dichloromethane, ethyl acetate) to give the title compound as a pale yellow powder (0. 057 g, 71% yield).
HRMS (EI) calcd for C 28 H 20 PO ([M + H] + ): 403.1252, observed 403.1245.
31 P NMR (CD- 2 Cl 2 , 160 MHz) δ -10.6.
UV-vis and Fluorescence in CH 2 Cl 2 : λ abs = 379 nm, λ em = 415 nm, Φ f = 0.83
実施例7,8
7)15b−チオホスファナフト[1,8−ab]ペリレン,8)15b-チオホスファ-ベンゾ[hi]ナフト[2,1-a]アセアンスリレンExamples 7 and 8
7) 15b-thiophosphanaphtho [1,8-ab] perylene, 8) 15b-thiophospha-benzo [hi] naphtho [2,1-a] acethrylene
1,1’−(2−ヨード−1,3−フェニレン)ジナフタレン(3.65g、8.0mmol)及びトルエン(50mL)にアルゴン雰囲気下−78℃で、t−ブチルリチウムのペンタン溶液(10.3mL、1.55M、16.0mmol)を添加し撹拌した。1時間後0℃に昇温しさらに1時間撹拌した後、−78℃で三塩化リン(1.65g、12.0mmol)を加え、1時間撹拌した後、室温で1時間攪拌した。溶媒を減圧下留去し、1,2−ジクロロベンゼン(80mL)を加えた後、三塩化アルミニウム(4.27g、32.0mmol)及び硫黄(0.385g、12.0mmol)を添加し、80℃で12時間撹拌した。1,4−ジアザビシクロ[2.2.2.]オクタン(4.03g、36.0mmol)を加えた後、溶媒を減圧下加熱して留去し、濾過して得られた粗生成物をシリカゲルカラムクロマトグラフィー(溶媒:トルエン、ジクロロメタン)により単離することで淡黄色粉末として15b−チオホスファナフト[1,8−ab]ペリレン(0.312g、収率10%)、15b-チオホスファ-ベンゾ[hi]ナフト[2,1-a]アセアンスリレン(0.843g、収率27%)をそれぞれ得た。
7)HRMS(FAB) m/z; calcd. 391.0710[M+H]+; found 391.0712
31P NMR (δppm in CD2Cl2); -7.6
X-ray crystal structure of 61,1 ′-(2-iodo-1,3-phenylene) dinaphthalene (3.65 g, 8.0 mmol) and toluene (50 mL) at −78 ° C. in an argon atmosphere at −78 ° C. 3 mL, 1.55 M, 16.0 mmol) was added and stirred. After 1 hour, the temperature was raised to 0 ° C. and the mixture was further stirred for 1 hour. Phosphorus trichloride (1.65 g, 12.0 mmol) was added at −78 ° C., and the mixture was stirred for 1 hour and then stirred at room temperature for 1 hour. The solvent was distilled off under reduced pressure, 1,2-dichlorobenzene (80 mL) was added, then aluminum trichloride (4.27 g, 32.0 mmol) and sulfur (0.385 g, 12.0 mmol) were added, and 80 Stir at 12 ° C. for 12 hours. 1,4-diazabicyclo [2.2.2. ] After adding octane (4.03 g, 36.0 mmol), the solvent was distilled off by heating under reduced pressure, and the crude product obtained by filtration was purified by silica gel column chromatography (solvent: toluene, dichloromethane). 15b-thiophosphanaphtho [1,8-ab] perylene (0.312 g, 10% yield), 15b-thiophospha-benzo [hi] naphtho [2,1-a] ASEAN as light yellow powder Sulylene (0.843 g, 27% yield) was obtained.
7) HRMS (FAB) m / z; calcd. 391.0710 [M + H] + ; found 391.0712
31 P NMR (δppm in CD 2 Cl 2 ); -7.6
X-ray crystal structure of 6
8)HRMS(FAB) m/z; calcd. 391.0710[M+H]+; found 391.0714
31P NMR (δppm in CD2Cl2); 17.7
X-ray crystal structure of 78) HRMS (FAB) m / z; calcd. 391.0710 [M + H] + ; found 391.0714
31 P NMR (δppm in CD 2 Cl 2 ); 17.7
X-ray crystal structure of 7
実施例9
6,10−ジメチル−8−(N,N−ジフェニルアミノ)−15b−チオホスファナフト[1,8−ab]ペリレンExample 9
6,10-Dimethyl-8- (N, N-diphenylamino) -15b-thiophosphanaphtho [1,8-ab] perylene
4−ヨード−3,5−ビス(2−メチルナフタレン−1−イル)−N,N−ジフェニルアニリン(1.30g、2.00mmol)及びテトラヒドロフラン(12mL)にアルゴン雰囲気下−78℃で、t−ブチルリチウムのペンタン溶液(2.60mL、1.55M、4.00mmol)を添加し1時間撹拌した後−78℃で三塩化リン(0.412g、3.00mmol)を加え、1時間撹拌した。溶媒を減圧下留去し、1,2−ジクロロベンゼン(24mL)を加えた後、三塩化アルミニウム(1.07g、8.00mmol)及び硫黄(0.064g、2.00mmol)を添加し、120℃で14時間撹拌した。1,4−ジアザビシクロ[2.2.2.]オクタン(1.12g、10.0mmol)を加えた後、溶媒を減圧下加熱して留去し、濾過して得られた粗生成物をシリカゲルカラムクロマトグラフィー(溶媒:トルエン、ジクロロメタン)により単離することで淡黄色粉末として標題化合物(0.253g、収率22%)を得た。
HRMS(FAB) m/z; calcd. 586.1758[M+H]+; found 586.1759
31P NMR (δppm in CD2Cl2); -7.84-Iodo-3,5-bis (2-methylnaphthalen-1-yl) -N, N-diphenylaniline (1.30 g, 2.00 mmol) and tetrahydrofuran (12 mL) at −78 ° C. under argon atmosphere at t -A pentane solution of butyllithium (2.60 mL, 1.55 M, 4.00 mmol) was added and stirred for 1 hour, and then phosphorus trichloride (0.412 g, 3.00 mmol) was added at -78 ° C and stirred for 1 hour. . The solvent was distilled off under reduced pressure, 1,2-dichlorobenzene (24 mL) was added, and then aluminum trichloride (1.07 g, 8.00 mmol) and sulfur (0.064 g, 2.00 mmol) were added. Stir at 14 ° C. for 14 hours. 1,4-diazabicyclo [2.2.2. ] After octane (1.12 g, 10.0 mmol) was added, the solvent was distilled off by heating under reduced pressure, and the crude product obtained by filtration was purified by silica gel column chromatography (solvent: toluene, dichloromethane). By separation, the title compound (0.253 g, yield 22%) was obtained as a pale yellow powder.
HRMS (FAB) m / z; calcd. 586.1758 [M + H] + ; found 586.1759
31 P NMR (δppm in CD 2 Cl 2 ); -7.8
実施例10
6,10−ジメチル−8−(N,N−ジフェニルアミノ)−15b−オキソホスファナフト[1,8−ab]ペリレンExample 10
6,10-Dimethyl-8- (N, N-diphenylamino) -15b-oxophosphanaphtho [1,8-ab] perylene
6,10−ジメチル−8−(N,N−ジフェニルアミノ)−15b−チオホスファナフト[1,8−ab]ペリレン(0.117g、0.20mmol)及びジクロロメタン(2.0mL)に対し30%過酸化水素水(2.0mL)を添加し、室温で6時間攪拌した。抽出した有機層の溶媒を減圧下留去し、得られた粗生成物をシリカゲルカラムクロマトグラフィー(溶媒:ジクロロメタン、酢酸エチル)により単離することで淡黄色粉末として標題化合物を得た(0.091g、収率80%)。
HRMS(FAB) m/z; calcd. 570.1987[M+H]+; found 570.1989
31P NMR (δppm in CD2Cl2); -9.3
X-ray crystal structure of 930 for 6,10-dimethyl-8- (N, N-diphenylamino) -15b-thiophosphanaphtho [1,8-ab] perylene (0.117 g, 0.20 mmol) and dichloromethane (2.0 mL). % Hydrogen peroxide solution (2.0 mL) was added, and the mixture was stirred at room temperature for 6 hours. The solvent of the extracted organic layer was distilled off under reduced pressure, and the resulting crude product was isolated by silica gel column chromatography (solvent: dichloromethane, ethyl acetate) to give the title compound as a pale yellow powder (0. 091 g, yield 80%).
HRMS (FAB) m / z; calcd. 570.1987 [M + H] + ; found 570.1989
31 P NMR (δppm in CD 2 Cl 2 ); -9.3
X-ray crystal structure of 9
実施例11
6,10−ジメチル−15b−(メチルシラ)ナフト[1,8−ab]ペリレン
合成例1:Example 11
6,10-Dimethyl-15b- (methylsila) naphtho [1,8-ab] perylene Synthesis Example 1:
1,1’−(2−ヨード−1,3−フェニレン)ビス(2−メチルナフタレン)(0.484g、1.00mmol)及びトルエン(5.0mL)にアルゴン雰囲気下−78℃で、t−ブチルリチウムのペンタン溶液(1.28mL、1.56M、1.20mmol)を添加し撹拌した。1時間後0℃に昇温しさらに1時間撹拌した後、−78℃でトリヨードメチルシラン(0.424g、1.00mmol)を加え、3時間撹拌した。溶媒を減圧下留去し、1,2−ジクロロベンゼン(10mL)を加えた後、三塩化アルミニウム(0.533g、4.00mmol)を添加し、60-120℃で撹拌した。1,4−ジアザビシクロ[2.2.2.]オクタン(1.12g、10.0mmol)を加えた後、溶媒を減圧下加熱して留去し、濾過して得られた粗生成物をHPLCおよびGPCで単離することで淡黄色粉末として標題化合物を得た(0.040g、収率10%)。
HRMS(FAB) m/z; calcd. 399.1569 [M+H]+; found 399.1570
29Si NMR (δppm in C6D6); -21.4
合成例2:1,1 ′-(2-iodo-1,3-phenylene) bis (2-methylnaphthalene) (0.484 g, 1.00 mmol) and toluene (5.0 mL) at −78 ° C. under argon atmosphere at t− A solution of butyllithium in pentane (1.28 mL, 1.56 M, 1.20 mmol) was added and stirred. After 1 hour, the temperature was raised to 0 ° C. and the mixture was further stirred for 1 hour, and then triiodomethylsilane (0.424 g, 1.00 mmol) was added at −78 ° C., followed by stirring for 3 hours. The solvent was evaporated under reduced pressure, 1,2-dichlorobenzene (10 mL) was added, aluminum trichloride (0.533 g, 4.00 mmol) was added, and the mixture was stirred at 60-120 ° C. 1,4-diazabicyclo [2.2.2. ] After octane (1.12 g, 10.0 mmol) was added, the solvent was distilled off by heating under reduced pressure, and the crude product obtained by filtration was isolated by HPLC and GPC as a pale yellow powder. The title compound was obtained (0.040 g, 10% yield).
HRMS (FAB) m / z; calcd. 399.1569 [M + H] + ; found 399.1570
29 Si NMR (δppm in C 6 D 6 ); -21.4
Synthesis example 2:
1,1’−(2−ヨード−1,3−フェニレン)ビス(2−メチルナフタレン)(0.242g、0.50mmol)及びトルエン(5.0mL)にアルゴン雰囲気下−78℃で、t−ブチルリチウムのペンタン溶液(1.28mL、1.56M、1.00mmol)を添加し撹拌した。1時間後0℃に昇温しさらに1時間撹拌した後、−78℃でクロロメチルシラン(0.060g、0.75mmol)を加え、3時間撹拌した。溶媒を減圧下留去し、ヘキサンで抽出した後再度溶媒を留去し、ジクロロエタン溶液とした。2,6−ルチジン(0.129g、1.20mmol)にトリチルテトラキス(ペンタフルオロフェニル)ボレート(0.922g、1.00mmol)を加え40-80℃で撹拌した。トリエチルアミン(4.0mL)を加えた後、溶媒を減圧下加熱して留去し、濾過して得られた粗生成物をHPLCおよびGPCで単離することで淡黄色粉末として標題化合物を得た(0.014g、収率7%)。 1,1 ′-(2-iodo-1,3-phenylene) bis (2-methylnaphthalene) (0.242 g, 0.50 mmol) and toluene (5.0 mL) at −78 ° C. in an argon atmosphere at t− A solution of butyllithium in pentane (1.28 mL, 1.56 M, 1.00 mmol) was added and stirred. After 1 hour, the temperature was raised to 0 ° C. and the mixture was further stirred for 1 hour, and chloromethylsilane (0.060 g, 0.75 mmol) was added at −78 ° C., followed by stirring for 3 hours. The solvent was distilled off under reduced pressure and extracted with hexane, and then the solvent was distilled off again to obtain a dichloroethane solution. Trityltetrakis (pentafluorophenyl) borate (0.922 g, 1.00 mmol) was added to 2,6-lutidine (0.129 g, 1.20 mmol), and the mixture was stirred at 40-80 ° C. After adding triethylamine (4.0 mL), the solvent was evaporated by heating under reduced pressure, and the crude product obtained by filtration was isolated by HPLC and GPC to obtain the title compound as a pale yellow powder. (0.014 g, 7% yield).
実施例12
N−(アントラセン−9−イル)−N−(2,6−ジクロロフェニル)アントラセン−9−アミンExample 12
N- (anthracen-9-yl) -N- (2,6-dichlorophenyl) anthracene-9-amine
2,6−ジクロロアニリン(0.162g、1.00mmol)、9−ヨードアントラセン(1.22g、4.01mmol)、銅粉(0.127g、2.00mmol)、炭酸カリウム(0.553g、4.00mmol)、18−クラウン−6−エーテル(0.013g、0.05mmol)にアルゴン雰囲気下室温で、ウンデカン(2mL)を加え190℃で16時間加熱撹拌した。ジクロロメタンを加えた後、固形物を濾過して除き、溶媒を減圧下留去しヘキサンを加えトリチュレーションすることで、黄褐色粉末として標題化合物を得た(0.283g、収率55%)。
1H NMR (δppm in CD2Cl2); 6.85(t, 2H, J = 8.1 Hz), 7.04-7.21(m, 8H), 7.32-7.50(m, 6H), 8.19(d, 2H, J = 8.6 Hz), 8.29(d, 2H, J= 8.6 Hz), 8.73(s, 1H); 13C NMR (δppm in CD2Cl2); 120.7, 123.2, 124.2(2C), 125.8(2C), 126.1(2C), 126.2(2C), 126.4(2C), 126.9(2C), 127.5(2C), 127.8, 129.0(2C), 129.3(4C), 129.9(2C), 132.0(4C), 132.1(2C), 133.4, 134.5(2C)2,6-dichloroaniline (0.162 g, 1.00 mmol), 9-iodoanthracene (1.22 g, 4.01 mmol), copper powder (0.127 g, 2.00 mmol), potassium carbonate (0.553 g, 4 0.006 mmol), 18-crown-6-ether (0.013 g, 0.05 mmol) was added undecane (2 mL) at room temperature under an argon atmosphere, and the mixture was heated and stirred at 190 ° C. for 16 hours. After adding dichloromethane, the solid was filtered off, the solvent was distilled off under reduced pressure, and hexane was added to perform trituration to obtain the title compound as a tan powder (0.283 g, yield 55%). .
1 H NMR (δppm in CD 2 Cl 2 ); 6.85 (t, 2H, J = 8.1 Hz), 7.04-7.21 (m, 8H), 7.32-7.50 (m, 6H), 8.19 (d, 2H, J = 8.6 Hz), 8.29 (d, 2H, J = 8.6 Hz), 8.73 (s, 1H); 13 C NMR (δppm in CD 2 Cl 2 ); 120.7, 123.2, 124.2 (2C), 125.8 (2C), 126.1 (2C), 126.2 (2C), 126.4 (2C), 126.9 (2C), 127.5 (2C), 127.8, 129.0 (2C), 129.3 (4C), 129.9 (2C), 132.0 (4C), 132.1 (2C) , 133.4, 134.5 (2C)
実施例13
19c-アザアントラ[9,1−ab]ベンゾ[o]ペリレン
合成例1:Example 13
19c-azaanthra [9,1-ab] benzo [o] perylene synthesis example 1:
N−(アントラセン−9−イル)−N−(2,6−ジクロロフェニル)アントラセン−9−アミン(0.206g、0.40mmol)、酢酸パラジウム(0.090g、0.40mmol)、炭酸カリウム(0.414g、3.0mmol)、テトラブチルアンモニウムブロミド(0.258g、0.80mmol)にアルゴン雰囲気下室温で、無水DMA(10mL)を加え120℃から180℃で撹拌した。溶媒を減圧下留去し、得られた粗生成物をHPLCおよびGPCで単離することで粉末として標題化合物を得ることができる。
合成例2:N- (anthracen-9-yl) -N- (2,6-dichlorophenyl) anthracen-9-amine (0.206 g, 0.40 mmol), palladium acetate (0.090 g, 0.40 mmol), potassium carbonate (0 414 g, 3.0 mmol) and tetrabutylammonium bromide (0.258 g, 0.80 mmol) were added anhydrous DMA (10 mL) at room temperature under an argon atmosphere, and the mixture was stirred at 120 to 180 ° C. The title compound can be obtained as a powder by evaporating the solvent under reduced pressure and isolating the resulting crude product by HPLC and GPC.
Synthesis example 2:
N−(アントラセン−9−イル)−N−(2,6−ジブロモフェニル)アントラセン−9−アミン(0.241g、0.40mmol)、酢酸パラジウム(0.090g、0.40mmol)、炭酸カリウム(0.414g、3.0mmol)、テトラブチルアンモニウムブロミド(0.258g、0.80mmol)にアルゴン雰囲気下室温で、無水DMA(10mL)を加え120℃から180℃で撹拌した。溶媒を減圧下留去し、得られた粗生成物をHPLCおよびGPCで単離することで粉末として標題化合物を得ることができる。 N- (anthracen-9-yl) -N- (2,6-dibromophenyl) anthracen-9-amine (0.241 g, 0.40 mmol), palladium acetate (0.090 g, 0.40 mmol), potassium carbonate ( 0.414 g, 3.0 mmol) and tetrabutylammonium bromide (0.258 g, 0.80 mmol) were added anhydrous DMA (10 mL) at room temperature under an argon atmosphere, and the mixture was stirred at 120 to 180 ° C. The title compound can be obtained as a powder by evaporating the solvent under reduced pressure and isolating the resulting crude product by HPLC and GPC.
実施例14
ベンゾ[kl]ベンゾ[4,5]インドロ[3,2,1−de]ペリレンExample 14
Benzo [kl] benzo [4,5] indolo [3,2,1-de] perylene
N−(2,6−ジブロモフェニル)−2−メチル−N−(2−メチルナフタレン−1−イル)ナフタレン−1−アミン(0.213g、0.40mmol)、酢酸パラジウム(0.090g、0.40mmol)、炭酸カリウム(0.414g、3.0mmol)、テトラブチルアンモニウムブロミド(0.258g、0.80mmol)にアルゴン雰囲気下室温で、無水DMA(10mL)を加え120℃から180℃で撹拌した。溶媒を減圧下留去し、得られた粗生成物をHPLCおよびGPCで単離することで粉末として標題化合物を得ることができる。 N- (2,6-dibromophenyl) -2-methyl-N- (2-methylnaphthalen-1-yl) naphthalen-1-amine (0.213 g, 0.40 mmol), palladium acetate (0.090 g, 0 .40 mmol), potassium carbonate (0.414 g, 3.0 mmol), and tetrabutylammonium bromide (0.258 g, 0.80 mmol) were added anhydrous DMA (10 mL) at room temperature under an argon atmosphere and stirred at 120 to 180 ° C. did. The title compound can be obtained as a powder by evaporating the solvent under reduced pressure and isolating the resulting crude product by HPLC and GPC.
実施例15
1, 1', 1'', 1'''-(3,6−ジヨードベンゼン−1,2,4,5−テトライル)テトラキス(2−メチルナフタレン)Example 15
1, 1 ′, 1 ″, 1 ′ ″-(3,6-diiodobenzene-1,2,4,5-tetrayl) tetrakis (2-methylnaphthalene)
ヘキサブロモベンゼン(16.5g、30mmol)に、アルゴン雰囲気下0℃で(2−メチルナフタレン−1−イル)マグネシウムブロミドのTHF溶液(200mL、1.20M、240mmol)を添加し室温で時間撹拌した。0℃でヨウ素のTHF溶液(144mL、1.67M、240mmol)を加えた後、室温下、チオ硫酸ナトリウム飽和水溶液300mLを加え、有機層を回収し、水層をジクロロメタンを用いて3回抽出した。合わせた有機抽出物に含まれる水分を硫酸マグネシウムで除去し、濾過した。溶媒を減圧下に留去した後、得られた褐色の油状物質にジエチルエーテルを用いてトリチュレーションすることで、白褐色粉末として標題化合物を得た(5.1g、収率19%)。 To hexabromobenzene (16.5 g, 30 mmol) was added a THF solution (200 mL, 1.20 M, 240 mmol) of (2-methylnaphthalen-1-yl) magnesium bromide at 0 ° C. under an argon atmosphere, and the mixture was stirred at room temperature for an hour. . After adding a THF solution of iodine (144 mL, 1.67 M, 240 mmol) at 0 ° C., 300 mL of a saturated aqueous solution of sodium thiosulfate was added at room temperature, the organic layer was recovered, and the aqueous layer was extracted three times with dichloromethane. . Water contained in the combined organic extracts was removed with magnesium sulfate and filtered. After the solvent was distilled off under reduced pressure, the resulting brown oily substance was triturated with diethyl ether to give the title compound as a white brown powder (5.1 g, yield 19%).
実施例16
3b,15b−ビス(チオホスファ)−9,10,21,22−テトラメチル−ジベンゾ[de,op]ジフェナレニノ[3,2,1-hi:3',2',1'-st]ペンタセンExample 16
3b, 15b-bis (thiophospha) -9,10,21,2-tetramethyl-dibenzo [de, op] diphenaleno [3,2,1-hi: 3 ′, 2 ′, 1′-st] pentacene
1, 1', 1'', 1'''-(3,6−ジヨードベンゼン−1,2,4,5−テトライル)テトラキス(2−メチルナフタレン)(4.45g、5.0mmol)及びTHF(50mL)に、アルゴン雰囲気下−78℃で、t−ブチルリチウムのペンタン溶液(14.5mL、1.55M、22.5mmol)を添加し撹拌した。0℃に昇温した後、−78℃でビス(ジエチルアミノ)クロロホスフィンのTHF溶液(7.0mL、2.0M、14.0mmol)を添加した。室温にした反応溶液の溶媒を減圧下に留去し、メタノールを用いてトリチュレーションして得られた白褐色粉末(3.50g)に,クロロベンゼン(35mL)と硫黄(0.28g、8.8mmol)を室温で8時間撹拌した。溶媒を減圧下留去し、メタノールでトリチュレーションして得られた淡黄色粉末(3.10g)にアルゴン雰囲気下室温で、三塩化アルミニウム(3.20g、24.0mmol)及び1,2−ジクロロベンゼン(30mL)を加え、160℃で14時間撹拌した。1,4−ジアザビシクロ[2.2.2.]オクタン(3.14g、28.0mmol)を加えた後、溶媒を減圧下加熱して留去し、濾過して得られた粗生成物をシリカゲルカラムクロマトグラフィー(溶媒:トルエン、ジクロロメタン)により単離することで朱色粉末として標題化合物を得た(0.387g、収率10%)。
HRMS(FAB) m/z; calcd. 758.1421 [M]+; found 758.1422
31P NMR (δppm in CD2Cl2); 0.71, 1 ′, 1 ″, 1 ′ ″-(3,6-diiodobenzene-1,2,4,5-tetrayl) tetrakis (2-methylnaphthalene) (4.45 g, 5.0 mmol) and To THF (50 mL), a pentane solution of t-butyllithium (14.5 mL, 1.55 M, 22.5 mmol) was added and stirred at −78 ° C. under an argon atmosphere. After raising the temperature to 0 ° C., a THF solution of bis (diethylamino) chlorophosphine (7.0 mL, 2.0 M, 14.0 mmol) was added at −78 ° C. The solvent of the reaction solution brought to room temperature was distilled off under reduced pressure and triturated with methanol to obtain a white brown powder (3.50 g), chlorobenzene (35 mL) and sulfur (0.28 g, 8. 8 mmol) was stirred at room temperature for 8 hours. The solvent was distilled off under reduced pressure, and trituration with methanol was performed on a pale yellow powder (3.10 g) at room temperature under an argon atmosphere at room temperature, with aluminum trichloride (3.20 g, 24.0 mmol) and 1,2- Dichlorobenzene (30 mL) was added and stirred at 160 ° C. for 14 hours. 1,4-diazabicyclo [2.2.2. ] After adding octane (3.14 g, 28.0 mmol), the solvent was distilled off by heating under reduced pressure, and the crude product obtained by filtration was purified by silica gel column chromatography (solvent: toluene, dichloromethane). The title compound was obtained as a vermilion powder by separation (0.387 g, yield 10%).
HRMS (FAB) m / z; calcd. 758.1421 [M] + ; found 758.1422
31 P NMR (δppm in CD 2 Cl 2 ); 0.7
実施例17
7b,14b,21b−トリス(チオホスファ)−4,11,18−トリメチル−トリアントラ [1,9,8-abcd:1',9',8'-ghij:1'',9'',8''-mnop]コロネンExample 17
7b, 14b, 21b-Tris (thiophospha) -4,11,18-trimethyl-trianthra [1,9,8-abcd: 1 ', 9', 8'-ghij: 1 ", 9", 8 ''-mnop] coronen
10,10',10''−(2,4,6−トリヨードベンゼン−1,3,5−トリイル)トリス(9-メチルアントラセン)(0.89g、1.0mmol)及びTHF(10mL)に、アルゴン雰囲気下−78℃で、ブチルリチウムのペンタン溶液(0.65mL、1.55M、1.0mmol)を添加し、0℃に昇温し1時間撹拌した。次いで,−78℃で、ビス(ジエチルアミノ)クロロホスフィンのTHF溶液(0.5mL、2.0M、1.0mmol)を添加し,0℃に昇温した。以上の操作を3回繰り返した後,反応溶液の溶媒を減圧下で留去し、メタノールを用いてトリチュレーションして得られた粉末に,クロロベンゼン(10mL)と硫黄(0.10g、3.0mmol)を室温下添加した。8時間後溶媒を減圧下留去し、メタノールでトリチュレーションして薄黄色粉末を得た.これに対し,アルゴン雰囲気下室温で、三塩化アルミニウム(1.20g、9.0mmol)及び1,2−ジクロロベンゼン(10mL)を加え、150℃で12時間撹拌した。1,4−ジアザビシクロ[2.2.2.]オクタン(1.68g、15.0mmol)を加えた後、溶媒を減圧下加熱して留去し、得られた粗生成物をHPLCおよびGPCで単離することで標題化合物を得ることができる。 To 10,10 ′, 10 ″-(2,4,6-triiodobenzene-1,3,5-triyl) tris (9-methylanthracene) (0.89 g, 1.0 mmol) and THF (10 mL) Then, a pentane solution of butyl lithium (0.65 mL, 1.55 M, 1.0 mmol) was added at −78 ° C. under an argon atmosphere, and the mixture was heated to 0 ° C. and stirred for 1 hour. Next, a THF solution (0.5 mL, 2.0 M, 1.0 mmol) of bis (diethylamino) chlorophosphine was added at −78 ° C., and the temperature was raised to 0 ° C. After the above operation was repeated three times, the solvent of the reaction solution was distilled off under reduced pressure, and trituration with methanol was performed to give chlorobenzene (10 mL) and sulfur (0.10 g, 3. 0 mmol) was added at room temperature. After 8 hours, the solvent was distilled off under reduced pressure and triturated with methanol to obtain a light yellow powder. To this, aluminum trichloride (1.20 g, 9.0 mmol) and 1,2-dichlorobenzene (10 mL) were added at room temperature under an argon atmosphere, and the mixture was stirred at 150 ° C. for 12 hours. 1,4-diazabicyclo [2.2.2. ] After octane (1.68 g, 15.0 mmol) was added, the solvent was evaporated by heating under reduced pressure, and the resulting crude product was isolated by HPLC and GPC to give the title compound. .
Claims (4)
(i) Z1、X、Z2が、それらが結合している炭素原子と一緒になって以下の式(A1)、(A2)または(A3)の構造を示す場合、X2、X1、X3は同一又は異なってR1を示すか、それらが結合している炭素原子と一緒になって各々Y7、Y8、Y9を示す。Y1〜Y15は同一または異なって、NまたはCR1を示す。Xはヘテロ原子もしくはその誘導体またはCR1を示す。
(i) when Z 1 , X, Z 2 together with the carbon atom to which they are attached show the structure of the following formula (A1), (A2) or (A3), X 2 , X 1 , X 3 are the same or different and each represents R 1 , or together with the carbon atom to which they are bonded, each represents Y 7 , Y 8 , Y 9 . Y 1 to Y 15 are the same or different and represent N or CR 1 . X represents a hetero atom or a derivative thereof or CR 1 .
X、X1、X2、X3は同一又は異なってヘテロ原子もしくはその誘導体またはCR1を示す。)The compound of Claim 1 represented by the following general formula (IA1), (IA2), (IA3), (IA4) or (IA5).
X, X 1 , X 2 and X 3 are the same or different and each represents a hetero atom or a derivative thereof or CR 1 . )
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