JP6430709B2 - 電子フィルムおよびデバイス用のキナゾリン誘導化合物 - Google Patents
電子フィルムおよびデバイス用のキナゾリン誘導化合物 Download PDFInfo
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- JP6430709B2 JP6430709B2 JP2014050807A JP2014050807A JP6430709B2 JP 6430709 B2 JP6430709 B2 JP 6430709B2 JP 2014050807 A JP2014050807 A JP 2014050807A JP 2014050807 A JP2014050807 A JP 2014050807A JP 6430709 B2 JP6430709 B2 JP 6430709B2
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- heteroaryl
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- 150000001875 compounds Chemical class 0.000 title claims description 81
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 title description 2
- 239000000203 mixture Substances 0.000 claims description 68
- 125000001424 substituent group Chemical group 0.000 claims description 60
- 125000003118 aryl group Chemical group 0.000 claims description 56
- 125000001072 heteroaryl group Chemical group 0.000 claims description 53
- 229910052805 deuterium Inorganic materials 0.000 claims description 38
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 35
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 27
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 18
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 17
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 235000010290 biphenyl Nutrition 0.000 claims description 8
- 239000004305 biphenyl Substances 0.000 claims description 8
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 84
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 56
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 56
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 51
- 239000007787 solid Substances 0.000 description 49
- 229910052757 nitrogen Inorganic materials 0.000 description 38
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 34
- 238000005481 NMR spectroscopy Methods 0.000 description 32
- 238000006243 chemical reaction Methods 0.000 description 32
- 239000010410 layer Substances 0.000 description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- -1 dimethyl-2-fluorenyl Chemical group 0.000 description 27
- 239000000463 material Substances 0.000 description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- 239000000243 solution Substances 0.000 description 19
- 239000002904 solvent Substances 0.000 description 16
- 229910052751 metal Inorganic materials 0.000 description 15
- 239000002184 metal Substances 0.000 description 15
- GJAWHXHKYYXBSV-UHFFFAOYSA-N quinolinic acid Chemical compound OC(=O)C1=CC=CN=C1C(O)=O GJAWHXHKYYXBSV-UHFFFAOYSA-N 0.000 description 15
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- 239000012044 organic layer Substances 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- 238000002390 rotary evaporation Methods 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- 235000019439 ethyl acetate Nutrition 0.000 description 12
- 239000002243 precursor Substances 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 10
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 8
- 238000003818 flash chromatography Methods 0.000 description 7
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 235000019341 magnesium sulphate Nutrition 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- TUQSVSYUEBNNKQ-UHFFFAOYSA-N 2,4-dichloroquinazoline Chemical compound C1=CC=CC2=NC(Cl)=NC(Cl)=C21 TUQSVSYUEBNNKQ-UHFFFAOYSA-N 0.000 description 6
- 229940125904 compound 1 Drugs 0.000 description 6
- 229940125782 compound 2 Drugs 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 239000008367 deionised water Substances 0.000 description 5
- 229910021641 deionized water Inorganic materials 0.000 description 5
- 239000002019 doping agent Substances 0.000 description 5
- IMKMFBIYHXBKRX-UHFFFAOYSA-M lithium;quinoline-2-carboxylate Chemical group [Li+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IMKMFBIYHXBKRX-UHFFFAOYSA-M 0.000 description 5
- 238000004809 thin layer chromatography Methods 0.000 description 5
- 230000032258 transport Effects 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000000151 deposition Methods 0.000 description 4
- 230000008021 deposition Effects 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 229940062627 tribasic potassium phosphate Drugs 0.000 description 4
- 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 3
- DXRLALXPCIOIDK-UHFFFAOYSA-N 2-(4-bromophenyl)-1-phenylbenzimidazole Chemical compound C1=CC(Br)=CC=C1C1=NC2=CC=CC=C2N1C1=CC=CC=C1 DXRLALXPCIOIDK-UHFFFAOYSA-N 0.000 description 3
- YKBLCBIZZLNAQU-UHFFFAOYSA-N 2-chloro-4-(9,9-dimethylfluoren-2-yl)quinazoline Chemical compound C1=CC=C2C(C3=CC=C4C5=CC=CC=C5C(C4=C3)(C)C)=NC(Cl)=NC2=C1 YKBLCBIZZLNAQU-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 125000000732 arylene group Chemical group 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 150000001975 deuterium Chemical group 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 125000005549 heteroarylene group Chemical group 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 3
- 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 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 3
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- 239000007858 starting material Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- PEYQCEFPKMIOFP-UHFFFAOYSA-N 1-phenyl-2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]benzimidazole Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=C(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)C=C1 PEYQCEFPKMIOFP-UHFFFAOYSA-N 0.000 description 2
- DAZFRJAIIUPRQZ-UHFFFAOYSA-N 2-(9,9-dimethylfluoren-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=C(C=2C(=CC=CC=2)C2(C)C)C2=C1 DAZFRJAIIUPRQZ-UHFFFAOYSA-N 0.000 description 2
- YBBLCLGGCYVDDF-UHFFFAOYSA-N 4-(9,9-dimethylfluoren-2-yl)-2-(4-quinolin-8-ylphenyl)quinazoline Chemical compound CC1(C)c2ccccc2-c2ccc(cc12)-c1nc(nc2ccccc12)-c1ccc(cc1)-c1cccc2cccnc12 YBBLCLGGCYVDDF-UHFFFAOYSA-N 0.000 description 2
- BTEAMLUWLVUBFF-UHFFFAOYSA-N 5-(3-methylphenyl)-4-phenylcyclohexa-2,4-diene-1,1-diamine Chemical compound CC=1C=C(C=CC1)C1=C(C=CC(C1)(N)N)C1=CC=CC=C1 BTEAMLUWLVUBFF-UHFFFAOYSA-N 0.000 description 2
- DOJWOAAFCWAUOT-UHFFFAOYSA-N 9-(2-chloroquinazolin-4-yl)carbazole Chemical compound C1=CC=CC2=NC(Cl)=NC(N3C4=CC=CC=C4C4=CC=CC=C43)=C21 DOJWOAAFCWAUOT-UHFFFAOYSA-N 0.000 description 2
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- 238000003775 Density Functional Theory Methods 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- MHABMANUFPZXEB-UHFFFAOYSA-N O-demethyl-aloesaponarin I Natural products O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=C(O)C(C(O)=O)=C2C MHABMANUFPZXEB-UHFFFAOYSA-N 0.000 description 2
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- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
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- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 2
- 125000005104 aryl silyl group Chemical group 0.000 description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 2
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- ZDZHCHYQNPQSGG-UHFFFAOYSA-N binaphthyl group Chemical group C1(=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
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- 125000000592 heterocycloalkyl group Chemical group 0.000 description 2
- 238000004770 highest occupied molecular orbital Methods 0.000 description 2
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- 125000001624 naphthyl group Chemical group 0.000 description 2
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 229910000160 potassium phosphate Inorganic materials 0.000 description 2
- 235000011009 potassium phosphates Nutrition 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 125000005493 quinolyl group Chemical group 0.000 description 2
- 150000003839 salts Chemical group 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical group COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 2
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- UHOVQNZJYSORNB-RALIUCGRSA-N 1,2,3,4,5-pentadeuteriobenzene Chemical compound [2H]C1=CC([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-RALIUCGRSA-N 0.000 description 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- MNCMBBIFTVWHIP-UHFFFAOYSA-N 1-anthracen-9-yl-2,2,2-trifluoroethanone Chemical group C1=CC=C2C(C(=O)C(F)(F)F)=C(C=CC=C3)C3=CC2=C1 MNCMBBIFTVWHIP-UHFFFAOYSA-N 0.000 description 1
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- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
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- QYBNYPQRKRMMNX-UHFFFAOYSA-N 2-chloro-4-naphthalen-1-ylquinazoline Chemical compound C1=CC=CC2=NC(Cl)=NC(C=3C4=CC=CC=C4C=CC=3)=C21 QYBNYPQRKRMMNX-UHFFFAOYSA-N 0.000 description 1
- WMPTYRGXBUYONY-UHFFFAOYSA-N 2-chloroquinazoline Chemical class C1=CC=CC2=NC(Cl)=NC=C21 WMPTYRGXBUYONY-UHFFFAOYSA-N 0.000 description 1
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- MRWWWZLJWNIEEJ-UHFFFAOYSA-N 4,4,5,5-tetramethyl-2-propan-2-yloxy-1,3,2-dioxaborolane Chemical compound CC(C)OB1OC(C)(C)C(C)(C)O1 MRWWWZLJWNIEEJ-UHFFFAOYSA-N 0.000 description 1
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- SKNFJPSCBDOVGQ-UHFFFAOYSA-N 4-naphthalen-1-yl-2-[4-(1-phenylbenzimidazol-2-yl)phenyl]quinazoline Chemical compound C1(=CC=CC2=CC=CC=C12)C1=NC(=NC2=CC=CC=C12)C1=CC=C(C=C1)C1=NC2=C(N1C1=CC=CC=C1)C=CC=C2 SKNFJPSCBDOVGQ-UHFFFAOYSA-N 0.000 description 1
- RAFPKRKWQYIVDC-UHFFFAOYSA-N 8-(4-bromophenyl)quinoline Chemical compound BrC1=CC=C(C=C1)C=1C=CC=C2C=CC=NC=12 RAFPKRKWQYIVDC-UHFFFAOYSA-N 0.000 description 1
- YCMSIPICLSJYEZ-UHFFFAOYSA-N 8-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]quinoline Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=C(C=2C3=NC=CC=C3C=CC=2)C=C1 YCMSIPICLSJYEZ-UHFFFAOYSA-N 0.000 description 1
- LIVLEZPWGOHETM-UHFFFAOYSA-N 9,10-dinaphthalen-2-yl-2-n,2-n,6-n,6-n-tetraphenylanthracene-2,6-diamine Chemical compound C1=CC=CC=C1N(C=1C=C2C(C=3C=C4C=CC=CC4=CC=3)=C3C=CC(=CC3=C(C=3C=C4C=CC=CC4=CC=3)C2=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 LIVLEZPWGOHETM-UHFFFAOYSA-N 0.000 description 1
- VIZUPBYFLORCRA-UHFFFAOYSA-N 9,10-dinaphthalen-2-ylanthracene Chemical compound C12=CC=CC=C2C(C2=CC3=CC=CC=C3C=C2)=C(C=CC=C2)C2=C1C1=CC=C(C=CC=C2)C2=C1 VIZUPBYFLORCRA-UHFFFAOYSA-N 0.000 description 1
- XYZCWSNUCIQDRK-UHFFFAOYSA-N 9-[2-(9,9-dimethylfluoren-2-yl)quinazolin-4-yl]carbazole Chemical compound CC1(C2=CC=CC=C2C=2C=CC(=CC12)C1=NC2=CC=CC=C2C(=N1)N1C2=CC=CC=C2C=2C=CC=CC12)C XYZCWSNUCIQDRK-UHFFFAOYSA-N 0.000 description 1
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- 238000004057 DFT-B3LYP calculation Methods 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
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- 150000001204 N-oxides Chemical class 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
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- 239000002253 acid Substances 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 description 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 1
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- 125000000304 alkynyl group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 125000002078 anthracen-1-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([*])=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 125000000748 anthracen-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([H])=C([*])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
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- 150000001491 aromatic compounds Chemical class 0.000 description 1
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- UHOVQNZJYSORNB-MZWXYZOWSA-N benzene-d6 Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 description 1
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- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 description 1
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- 125000005874 benzothiadiazolyl group Chemical group 0.000 description 1
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- 150000001602 bicycloalkyls Chemical group 0.000 description 1
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- PBAYDYUZOSNJGU-UHFFFAOYSA-N chelidonic acid Natural products OC(=O)C1=CC(=O)C=C(C(O)=O)O1 PBAYDYUZOSNJGU-UHFFFAOYSA-N 0.000 description 1
- 238000005229 chemical vapour deposition Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
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- 239000013058 crude material Substances 0.000 description 1
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- 238000002425 crystallisation Methods 0.000 description 1
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- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000007405 data analysis Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
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- 238000001194 electroluminescence spectrum Methods 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 125000003838 furazanyl group Chemical group 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
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- 230000005283 ground state Effects 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000005570 heteronuclear single quantum coherence Methods 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
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- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- SZDXPEWZZGNIBB-UHFFFAOYSA-N n-[4-[4-(naphthalen-1-ylamino)phenyl]phenyl]naphthalen-1-amine Chemical compound C1=CC=C2C(NC=3C=CC(=CC=3)C=3C=CC(NC=4C5=CC=CC=C5C=CC=4)=CC=3)=CC=CC2=C1 SZDXPEWZZGNIBB-UHFFFAOYSA-N 0.000 description 1
- HUMMCEUVDBVXTQ-UHFFFAOYSA-N naphthalen-1-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=CC=CC2=C1 HUMMCEUVDBVXTQ-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
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- 238000012585 nuclear overhauser effect spectroscopy experiment Methods 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- KATIRQRAVXTBNY-UHFFFAOYSA-N quinolin-4-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=CC=NC2=C1 KATIRQRAVXTBNY-UHFFFAOYSA-N 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000012925 reference material Substances 0.000 description 1
- 230000008521 reorganization Effects 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical compound FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000006822 tri(C1-C30) alkylsilyl group Chemical group 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 238000000825 ultraviolet detection Methods 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/74—Quinazolines; Hydrogenated quinazolines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to ring carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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Description
本願は、2013年3月15日出願の米国特許仮出願第61/798460号の利点を主張するものである。
A)
i)(C6−C40)アリール、さらに(C6−C30)アリール(それぞれ置換基があってもなくてもよい)、または
ii)(C3−C40)ヘテロアリール、さらに(C3−C30)ヘテロアリール(それぞれ置換基があってもなくてもよい);
R2は、以下から選択され:
i)(C6−C40)アリール、さらに(C6−C30)アリール(それぞれ置換基があってもなくてもよい)、または
ii)(C3−C40)ヘテロアリール、さらに(C3−C30)ヘテロアリール(それぞれ置換基があってもなくてもよい)、
R3は、以下から選択され:
i)水素またはジュウテリウム、
ii)(C1−C20)アルキル、さらに(C1−C10)アルキル、
iii)(C6−C40)アリール、さらに(C6−C30)アリール(それぞれ置換基があってもなくてもよい)、または
iv)(C3−C40)ヘテロアリール、さらに(C3−C30)ヘテロアリール(それぞれ置換基があってもなくてもよい)、
式1は、少なくとも3つのC−N二重結合を含み;1個または複数の水素が、任意でジュウテリウムと置換されてよい;
B)
i)(C6−C40)アリール、さらに(C6−C30)アリール(それぞれ置換基があってもなくてもよい)、または
ii)(C3−C40)ヘテロアリール、さらに(C3−C30)ヘテロアリール(それぞれ置換基があってもなくてもよい);
R2’は、以下から選択され:
i)水素またはジュウテリウム、
ii)(C1−C20)アルキル、さらに(C1−C10)アルキル、
iii)(C6−C40)アリール、さらに(C6−C30)アリール(それぞれ置換基があってもなくてもよい)、または
iv)(C3−C40)ヘテロアリール、さらに(C3−C30)ヘテロアリール(それぞれ置換基があってもなくてもよい);
R3’およびR4’は、以下から独立して選択され:
i)水素またはジュウテリウム、
ii)(C1−C20)アルキル基、さらに(C1−C10)アルキル、
iii)(C6−C40)アリール、さらに(C6−C30)アリール(それぞれ置換基があってもなくてもよい)、または
iv)(C3−C40)ヘテロアリール、さらに(C3−C30)ヘテロアリール(それぞれ置換基があってもなくてもよい);
R5’は、以下から選択され:
i)水素またはジュウテリウム、
ii)(C1−C20)アルキル、さらに(C1−C10)アルキル、
iii)(C6−C40)アリール、さらに(C6−C30)アリール(それぞれ置換基があってもなくてもよい)、または
iv)(C3−C40)ヘテロアリール、さらに(C3−C30)ヘテロアリール(それぞれ置換基があってもなくてもよい)、
Lは、(C6−C30)アリーレンまたは(C3−C30)ヘテロアリーレンを含み;R1’がビフェニルを含む場合、カルバゾールを含まず;1個または複数の水素が、任意でジュウテリウムと置換されてよい;
C)
i)(C6−C40)アリール、さらに(C6−C30)アリール(それぞれ置換基があってもなくてもよい)、または
ii)(C3−C40)ヘテロアリール、さらに(C3−C30)ヘテロアリール(それぞれ置換基があってもなくてもよい);
R2”は、以下から選択され:
i)水素またはジュウテリウム、
ii)(C1−C20)アルキル、さらに(C1−C10)アルキル、
iii)(C6−C40)アリール、さらに(C6−C30)アリール(それぞれ置換基があってもなくてもよい)、または
iv)(C3−C40)ヘテロアリール、さらに(C3−C30)ヘテロアリール(それぞれ置換基があってもなくてもよい);
R3”およびR4”は、以下から独立して選択され:
i)水素またはジュウテリウム、
ii)(C1−C20)アルキル基、さらに(C1−C10)アルキル、
iii)(C6−C40)アリール、さらに(C6−C30)アリール(それぞれ置換基があってもなくてもよい)、または
iv)(C3−C40)ヘテロアリール、さらに(C3−C30)ヘテロアリール(それぞれ置換基があってもなくてもよい);
R5”は、以下から選択され:
i)水素またはジュウテリウム、
ii)(C1−C20)アルキル、さらに(C1−C10)アルキル、
iii)(C6−C40)アリール、さらに(C6−C30)アリール(それぞれ置換基があってもなくてもよい)、または
iv)(C3−C40)ヘテロアリール、さらに(C3−C30)ヘテロアリール(それぞれ置換基があってもなくてもよい);
R1”がビフェニルを含む場合、カルバゾールを含まず;1個または複数の水素が、任意でジュウテリウムと置換されてよい;ならびに
D)これらの組合せ。
ii)(C3−C30)ヘテロアリール(置換基があってもなくてもよい);
R2は、以下から選択され:
i)(C6−C30)アリール(置換基があってもなくてもよい)、または
ii)(C3−C30)ヘテロアリール(置換基があってもなくてもよい)、
R3は、以下から選択され:
i)水素またはジュウテリウム、
式1は、少なくとも3つのC−N二重結合を含み;1個または複数の水素が、任意でジュウテリウムと置換されてよく;
式2について、R1’は、以下から選択され:
i)(C6−C30)アリール(置換基があってもなくてもよい)、または
ii)(C3−C30)ヘテロアリール(置換基があってもなくてもよい);
R2’は、以下から選択され:
i)水素またはジュウテリウム、
R3’およびR4’は、以下から独立して選択され:
ii)(C1−C10)アルキル基、
R5’は、以下から選択され:
i)水素またはジュウテリウム、
Lは、(C6−C30)アリーレンまたは(C3−C30)ヘテロアリーレンを含み;R1’がビフェニルを含む場合、カルバゾールを含まず;1個または複数の水素が、任意でジュウテリウムと置換されてよく;
式3について、R1”は、以下から選択され:
i)(C6−C30)アリール(置換基があってもなくてもよい)、または
ii)(C3−C30)ヘテロアリール(置換基があってもなくてもよい);
R2”は、以下から選択され:
i)水素またはジュウテリウム、
R3”およびR4”は、以下から独立して選択され:
ii)(C1−C10)アルキル基、
R5”は、以下から選択され:
i)水素またはジュウテリウム、
R1”がビフェニルを含む場合、カルバゾールを含まず;1個または複数の水素が、任意でジュウテリウムと置換されてよい。
本発明のデバイスは、1つには本発明の組成物から形成された層を、もう1つには組成物Bから形成された層を含んでよく、この組成物Bは、少なくとも1つの「HTL化合物」を含む。HTL化合物は、低駆動電圧で正孔を輸送する材料である。高い正孔モビリティが推奨される。HTLは、放出層によって輸送される電子の通過をブロックするのを助けるために使用される。一般的に、電子親和度が小さいことが電子をブロックするために必要とされる。HTLは望ましくは、隣接するEML層からの励起子移動をブロックするために、より大きなトリプレットを有するべきである。HTL化合物の例として、ジ(p−トリル)アミノフェニル]−シクロヘキサン(TPAC)、N,N−ジフェニル−N,N−ビス(3−メチルフェニル)−1,1−ビフェニル−4,4−ジアミン(TPD)、およびN,N’−ジフェニル−N,N’−ビス(1−ナフチル)−(1,1’−ビフェニル)−4,4’−ジアミン(NPB)が挙げられるが、これらに限定されない。
本明細書中で記載される用語「アリール」は、芳香族炭化水素から、1個の水素原子を欠失させることによって誘導される有機ラジカルを表す。アリール基は、単環式環系および/または融合環系であってよく、各環は、適切には4から7個、好ましくは5または6個の原子を含む。2個以上のアリール基が単結合を介して組み合わされる構造も含まれる。具体的な例として、フェニル、ナフチル、ビナフチル(例えば1,1’−ビナフチル)、ビフェニル、アントリル、インデニル、フルオレニル(例えば9,9−(ジメチル−2−フルオレニル))、フェニルフルオレニル(例えば4−(9,9−ジメチル−2−フルオレニル)フェニル)、ベンゾフルオレニル、フェナントリル、トリフェニレニル、ピレニル、ペリレニル、クリセニル、ナフタセニル、フルオランテニル、フルオレニルナフチル(例えば9,9−(ジメチル)−2−フルオレニルナフチル)等が挙げられるが、これらに限定されない。ナフチルは、1−ナフチルまたは2−ナフチルであってよく、アントリルは、1−アントリル、2−アントリル、または9−アントリルであってよく、フルオレニルは、1−フルオレニル、2−フルオレニル、3−フルオレニル、4−フルオレニル、および9−フルオレニルの何れか1つであってよいが、これらに限らない。
[試薬および試験方法]
全ての溶媒および試薬を、Sigma−Aldrich、Fisher Scientific、Acros、TCIおよびAlfa Aesarを含む商業ベンダーから得、入手可能な最高純度で使用し、ならびに/または、必要に応じて、使用前に再結晶化させた。乾燥性の溶媒を、インハウス精製/分配系から得(ヘキサン、トルエン、テトラヒドロフランおよびジエチルエーテル)、またはSigma−Aldrichから購入した。感水性化合物に関わる全ての実験を、窒素雰囲気下の「オーブン乾燥」ガラス器具内で、またはグローブボックス内で行った。反応を、プレコーティングしたアルミニウムプレート(VWR60F254)上での分析的薄層クロマトグラフィー(TLC)によって、UV光および/または過マンガン酸カリウム染色により可視化して、監視した。フラッシュクロマトグラフィーを、GRACERESOLVカートリッジを備えたISCO COMBIFLASH系で実行した。
4−ブロモ−N−(2−(フェニルアミノ)フェニル)ベンズアミド(前駆体1)
1H NMR(400MHz,DMSO−d6)δ9.77(s,1H),7.84(d,J=8.6Hz,2H),7.70(d,J=8.6Hz,2H),7.54(dd,J=7.9,1.2Hz,1H),7.47(s,1H),7.30(dd,J=8.1,1.3Hz,1H),7.23−7.10(m,3H),7.00(td,J=7.8,1.4Hz,1H),6.92(dd,J=8.6,1.0Hz,2H),6.79(t,J=7.3Hz,1H).13C NMR(101MHz,DMSO−d6)δ164.68,143.88,137.06,133.67,131.24,129.80,129.02,128.74,126.53,126.10,125.20,121.36,119.69,119.53,116.61.
1H NMR(400MHz,CDCl3)δ7.91−7.85(m,1H),7.56−7.46(m,3H),7.43(s,4H),7.37−7.20(m,5H).13C NMR(101MHz,CDCl3)δ151.23,142.94,137.28,136.78,131.57,130.86,130.02,128.94,128.79,127.38,124.06,123.60,123.17,119.93,110.50.
1H NMR(400MHz,DMSO−d6)δ8.14(ブロード,1H),7.87−7.78(m,1H),7.78−7.73(m,1H),7.65−7.46(m,4H),7.47−7.38(m,2H),7.30(dtd,J=15.0,7.2,1.3Hz,2H),7.20(dd,J=7.2,0.8Hz,1H).13C NMR(101MHz,DMSO−d6)δ151.83,142.22,136.96,136.36,133.85,130.89,129.98,128.82,128.05,127.47,123.44,122.83,119.23,110.48.
1H NMR(400MHz,CDCl3)δ8.20(ddd,J=8.4,1.3,0.6Hz,1H),8.09−8.03(m,1H),7.98−7.85(m,3H),7.85−7.80(m,1H),7.78(dd,J=7.8,1.6Hz,1H),7.64(ddd,J=8.3,6.9,1.2Hz,1H),7.49(ddd,J=7.5,3.7,2.3Hz,1H),7.44−7.36(m,2H),1.57(s,6H).13C NMR(101MHz,CDCl3)δ172.01,157.11,154.33,154.11,153.13,141.93,138.08,134.74,134.62,129.65,128.33,128.13,127.91,127.63,127.27,124.64,122.81,121.78,120.74,120.10,47.22,27.12.
1H NMR(400MHz,CDCl3)δ8.17−8.11(m,3H),8.02−7.94(m,1H),7.89(ddd,J=8.5,1.4,0.7Hz,1H),7.58−7.49(m,1H),7.48−7.34(m,6H).
13C NMR(101MHz,CDCl3)δ159.97,156.72,154.65,139.99,135.65,128.31,127.75,126.48,126.33,125.11,122.27,120.33,118.57,112.07.
1H NMR(500MHz,CDCl3)δ8.14−8.08(m,1H),8.05(t,J=9.2Hz,1H),8.00−7.90(m,2H),7.69−7.58(m,3H),7.57−7.45(m,3H),7.45−7.38(m,1H).13C NMR(126MHz,CDCl3)δ172.37,157.10,152.56,135.25,133.58,133.11,131.25,130.46,128.49,128.13,128.03,127.96,127.73,127.11,126.47,125.24,124.99,123.30
1H NMR(400MHz,CDCl3)δ8.94(dd,J=4.2,1.8Hz,1H),8.20(dd,J=8.3,1.8Hz,1H),7.84(dd,J=8.1,1.5Hz,1H),7.70(dd,J=7.1,1.5Hz,1H),7.64−7.54(m,5H),7.42(dd,J=8.3,4.2Hz,1H).13C NMR(101MHz,CDCl3)δ150.36,145.81,139.65,138.41,136.31,132.26,131.14,130.09,128.77,127.93,126.28,121.79,121.16.
1H NMR(400MHz,CDCl3)δ8.94(dd,J=4.2,1.8Hz,1H),8.19(dd,J=8.3,1.8Hz,1H),7.99−7.89(m,2H),7.83(dd,J=8.1,1.5Hz,1H),7.76−7.66(m,3H),7.60(dd,J=8.1,7.2Hz,1H),7.40(dd,J=8.3,4.2Hz,1H),1.37(s,12H).13C NMR(101MHz,CDCl3)δ150.30,142.52,140.92,136.13,134.42,130.18,129.96,128.69,127.68,126.21,121.01,83.71,25.03,24.86.
1H NMR(400MHz,CDCl3)δ8.20(ddd,J=8.4,1.3,0.6Hz,1H),8.09−8.03(m,1H),7.98−7.85(m,3H),7.85−7.80(m,1H),7.78(dd,J=7.8,1.6Hz,1H),7.64(ddd,J=8.3,6.9,1.2Hz,1H),7.49(ddd,J=7.5,3.7,2.3Hz,1H),7.44−7.36(m,2H),1.57(s,6H).13C NMR(101MHz,CDCl3)δ172.01,157.11,154.33,154.11,153.13,141.93,138.08,134.74,134.62,129.65,128.33,128.13,127.91,127.63,127.27,124.64,122.81,121.78,120.74,120.10,47.22,27.12.
1H NMR(500MHz,CDCl3)δ8.66−8.59(m,2H),8.24(d,J=8.2Hz,1H),8.22−8.16(m,2H),8.00−7.91(m,2H),7.85(dd,J=8.4,0.7Hz,1H),7.80−7.73(m,2H),7.56−7.44(m,6H),7.45−7.34(m,7H),7.34−7.26(m,3H).13C NMR(126MHz,CDCl3)δ160.10,158.28,153.96,151.92,143.13,140.44,138.27,137.40,137.00,134.60,132.23,129.94,129.74,129.37,128.66,128.51,127.43,127.29,126.26,125.94,124.79,123.53,123.08,121.58,120.33,119.99,119.01,111.98,110.48.
1H NMR(500MHz,CDCl3)δ8.68−8.61(m,2H),8.19(ddd,J=8.5,1.1,0.7Hz,1H),8.10−8.04(m,1H),8.01−7.97(m,1H),7.95−7.87(m,2H),7.77−7.71(m,2H),7.69−7.58(m,4H),7.57−7.33(m,9H),7.33−7.28(m,1H),7.27−7.23(m,1H)
13C NMR(126MHz,CDCl3)δ168.99,159.58,151.99,151.38,143.00,138.89,137.29,136.93,134.70,133.90,133.61,131.69,131.51,129.84,129.71,129.56,128.94,128.54,128.33,127.81,127.37,127.23,127.19,126.64,126.17,125.60,124.98,123.39,123.36,122.97,119.84,110.39.
1H NMR(400MHz,CDCl3)δ8.78−8.74(m,1H),8.69(dd,J=8.0,1.6Hz,1H),8.30−8.22(m,1H),8.21−8.14(m,2H),7.91(ddd,J=8.4,6.9,1.4Hz,1H),7.88−7.73(m,3H),7.57−7.30(m,10H),1.58(s,6H).
13C NMR(101MHz,CDCl3)δ161.16,158.08,154.66,154.14,154.12,142.15,140.55,138.66,136.61,134.46,129.33,128.19,127.89,127.10,126.87,126.26,125.94,124.77,122.86,122.74,121.54,120.62,120.35,120.19,118.83,112.16,47.08,27.20.
1H NMR(400MHz,CDCl3)δ8.68(d,J=8.7Hz,2H),8.23−8.11(m,2H),7.96−7.89(m,4H),7.89−7.80(m,2H),7.76(d,J=8.7Hz,2H),7.58(ddd,J=8.2,6.9,1.2Hz,1H),7.55−7.45(m,4H),7.43−7.33(m,5H),7.32−7.26(m,2H),1.59(s,6H).
13C NMR(101MHz,CDCl3)δ168.77,159.48,154.26,153.88,152.18,152.03,143.14,141.22,139.07,138.38,137.37,137.06,136.30,133.63,131.77,129.94,129.67,129.51,129.21,128.54,128.04,127.47,127.21,124.59,123.47,123.07,122.77,121.91,120.59,120.08,119.96,110.49,47.16,27.16.
1H NMR(400MHz,CDCl3)δ9.03(dd,J=4.1,1.8Hz,1H),8.83−8.75(m,2H),8.33(dd,J=8.4,0.8Hz,1H),8.26(dd,J=8.3,1.8Hz,1H),8.22−8.17(m,1H),8.11−8.04(m,2H),8.01−7.94(m,2H),7.94−7.83(m,4H),7.83−7.78(m,1H),7.67(dd,J=8.0,7.2Hz,1H),7.57(ddd,J=8.2,6.9,1.2Hz,1H),7.52−7.44(m,2H),7.40−7.31(m,2H),1.62(s,6H).
13C NMR(101MHz,CDCl3)δ168.13,160.61,154.69,153.94,152.17,150.43,146.03,141.58,141.37,140.18,138.88,137.50,136.72,136.41,133.44,130.84,130.56,130.00,129.13,128.86,128.17,128.05,127.65,127.32,127.01,126.75,126.40,122.94,122.69,121.71,121.20,120.50,120.01,47.10,27.24.
1H NMR(400MHz,クロロホルム−d)δ8.99(dd,J=4.2,1.8Hz,1H),8.87(d,J=8.4Hz,2H),8.21(ddd,J=9.8,8.4,1.6Hz,3H),8.01(dd,J=1.4,0.8Hz,1H),7.98−7.87(m,5H),7.86−7.80(m,3H),7.64(dd,J=8.1,7.2Hz,1H),7.57(ddd,J=8.3,6.9,1.2Hz,1H),7.53−7.47(m,1H),7.47−7.36(m,3H),1.61(s,6H).13C NMR(101MHz,CDCl3)δ168.44,160.26,154.30,153.87,152.25,150.31,146.14,141.82,140.63,138.50,137.22,136.64,136.23,133.35,130.87,130.31,129.60,129.32,128.79,128.38,127.96,127.76,127.18,127.11,126.82,126.30,124.76,122.77,121.85,121.06,120.57,119.97,47.17,27.19.
全ての有機材料を、昇華によって精製してから堆積させた。OLEDを、陽極として機能するITO(インジウムスズ酸化物)コーティングしたガラス基質上へ製作し、頂部にアルミニウム陰極を配置した。全ての有機層を、ベース圧力が<10−7トルである真空チャンバ内での化学蒸着によって、熱的に堆積させた。有機層の堆積速度を0.1から0.05nm/sの間で維持した。アルミニウム陰極を、0.5nm/sで堆積させた。OLEDデバイスの作用面積は、陰極堆積のためのシャドーマスクによって規定されるように、「3mm×3mm」であった。ガラス基質(20mm×20mm)は、Samsung Corningから入手可能であり、ITO層厚は1500オングストロームであった。
化合物1および化合物2をそれぞれ、蛍光緑色OLEDにおいて試験した。結果を以下の表4に示す。化合物1または化合物2を含有するETL(電子移動層)フィルム層を含む本発明のフィルムは、参照フィルムよりも低い「ターンオン電圧」、およびより高い発光効率を示した。
[1]以下(A、B、CおよびD)からなる群から選択される少なくとも1つの化合物を含む組成物:
A)
式中、R1は、以下から選択され:
i)置換基があってもなくてもよい(C6−C40)アリール、または
ii)置換基があってもなくてもよい(C3−C40)ヘテロアリール;
R2は、以下から選択され:
i)置換基があってもなくてもよい(C6−C40)アリール、または
ii)置換基があってもなくてもよい(C3−C40)ヘテロアリール、
R3は、以下から選択され:
i)水素またはジュウテリウム、
ii)(C1−C20)アルキル、
iii)置換基があってもなくてもよい(C6−C40)アリール、または
iv)置換基があってもなくてもよい(C3−C40)ヘテロアリール、
式1は、少なくとも3つのC−N二重結合を含み;1個または複数の水素が、任意でジュウテリウムと置換されてよい;
B)
式中、R1’は、以下から選択され:
i)置換基があってもなくてもよい(C6−C40)アリール、または
ii)置換基があってもなくてもよい(C3−C40)ヘテロアリール;
R2’は、以下から選択され:
i)水素またはジュウテリウム、
ii)(C1−C20)アルキル、
iii)置換基があってもなくてもよい(C6−C40)アリール、または
iv)置換基があってもなくてもよい(C3−C40)ヘテロアリール;
R3’およびR4’は、以下から独立して選択され:
i)水素またはジュウテリウム、
ii)(C1−C20)アルキル基、
iii)置換基があってもなくてもよい(C6−C40)アリール、または
iv)置換基があってもなくてもよい(C3−C40)ヘテロアリール;
R5’は、以下から選択され:
i)水素またはジュウテリウム、
ii)(C1−C20)アルキル、
iii)置換基があってもなくてもよい(C6−C40)アリール、または
iv)置換基があってもなくてもよい(C3−C40)ヘテロアリール、
Lは、(C6−C30)アリーレンまたは(C3−C30)ヘテロアリーレンを含み;
R1’がビフェニルを含む場合、カルバゾールを含まず;1個または複数の水素が、任意でジュウテリウムと置換されてよい;
C)
式中、R1”は、以下から選択され:
i)置換基があってもなくてもよい(C6−C40)アリール、または
ii)置換基があってもなくてもよい(C3−C40)ヘテロアリール;
R2”は、以下から選択され:
i)水素またはジュウテリウム、
ii)(C1−C20)アルキル、
iii)置換基があってもなくてもよい(C6−C40)アリール、または
iv)置換基があってもなくてもよい(C3−C40)ヘテロアリール;
R3”およびR4”は、以下から独立して選択され:
i)水素またはジュウテリウム、
ii)(C1−C20)アルキル基、
iii)置換基があってもなくてもよい(C6−C30)アリール、または
iv)置換基があってもなくてもよい(C3−C30)ヘテロアリール;
R5”は、以下から選択され:
i)水素またはジュウテリウム、
ii)(C1−C20)アルキル、
iii)置換基があってもなくてもよい(C6−C40)アリール、または
iv)置換基があってもなくてもよい(C3−C40)ヘテロアリール;
R1”がビフェニルを含む場合、カルバゾールを含まず;1個または複数の水素が、任意でジュウテリウムと置換されてよい;ならびに
D)これらの組合せ。
[2]前記少なくとも1つの化合物は、式1からなる群から選択される、[1]記載の組成物。
[3]R1は、以下から選択される、[2]記載の組成物:
[4]R2は、以下から選択される、[2]または[3]記載の組成物:
[5]R1は、9個以上の炭素原子を含む、[2]から[4]の何れか一項に記載の組成物。
[6]R2は、9個以上の炭素原子を含む、[2]から[5]の何れか一項に記載の組成物。
[7]前記少なくとも1つの化合物は、式2からなる群から選択される、[1]記載の組成物。
[8]R1’は、以下から選択される、[7]記載の組成物:
[9]Lは、以下から選択される、[7]または[8]記載の組成物:フェニレンまたはナフタレン。
[10]R1’は、9個以上の炭素原子を含む、[7]から[9]の何れか一項に記載の組成物。
[11]R2’およびR5’はそれぞれ水素であり、R3’およびR4’はそれぞれメチルである、[7]から[10]の何れか一項に記載の組成物。
[12]前記少なくとも1つの化合物は、式3からなる群から選択される、[1]記載の組成物。
[13]R1”は、以下から選択される、[12]記載の組成物:
[14]前記少なくとも1つの化合物は、以下の化合物からなる群から選択される、[1]記載の組成物:
[15][1]から[14]の何れか一項に記載の組成物から形成される少なくとも1つの成分を含む電子デバイス。
Claims (8)
- 式1からなる群から選択される少なくとも1つの化合物を含む組成物:
式中、R1は、以下から選択され:
i)置換基があってもなくてもよい(C6−C40)アリール、または
ii)置換基があってもなくてもよい(C3−C40)ヘテロアリール;
R2は、以下から選択され:
i)置換基があってもなくてもよい(C6−C40)アリール、または
ii)置換基があってもなくてもよい(C3−C40)ヘテロアリール、
R3は、以下から選択され:
i)水素またはジュウテリウム、
ii)(C1−C20)アルキル、
iii)置換基があってもなくてもよい(C6−C40)アリール、または
iv)置換基があってもなくてもよい(C3−C40)ヘテロアリール、
式1は、少なくとも3つのC−N二重結合を含み;1個または複数の水素が、任意でジュウテリウムと置換されてよく、
R1は、以下から選択されるか:
または、R2は、以下から選択される:
前記組成物。 - R1は、9個以上の炭素原子を含む、請求項1に記載の組成物。
- 式2からなる群から選択される少なくとも1つの化合物を含む組成物:
式中、R1’は、以下から選択され:
i)置換基があってもなくてもよい(C6−C40)アリール、または
ii)置換基があってもなくてもよい(C3−C40)ヘテロアリール;
R2’は、以下から選択され:
i)水素またはジュウテリウム、
ii)(C1−C20)アルキル、
iii)置換基があってもなくてもよい(C6−C40)アリール、または
iv)置換基があってもなくてもよい(C3−C40)ヘテロアリール;
R3’およびR4’は、以下から独立して選択され:
i)水素またはジュウテリウム、
ii)(C1−C20)アルキル基、
iii)置換基があってもなくてもよい(C6−C40)アリール、または
iv)置換基があってもなくてもよい(C3−C40)ヘテロアリール;
R5’は、以下から選択され:
i)水素またはジュウテリウム、
ii)(C1−C20)アルキル、
iii)置換基があってもなくてもよい(C6−C40)アリール、または
iv)置換基があってもなくてもよい(C3−C40)ヘテロアリール、
Lは、フェニレンまたはナフタレンであり;
R1’がビフェニルを含む場合、カルバゾールを含まず;1個または複数の水素が、任意でジュウテリウムと置換されてよい;前記組成物。 - R1’は、以下から選択される、請求項3記載の組成物:
- R1’は、9個以上の炭素原子を含む、請求項3に記載の組成物。
- R2’およびR5’はそれぞれ水素であり、R3’およびR4’はそれぞれメチルである、請求項3から請求項5の何れか一項に記載の組成物。
- 以下の化合物からなる群から選択される化合物を含む組成物:
- 請求項1から請求項7の何れか一項に記載の組成物から形成される少なくとも1つの成分を含む電子デバイス。
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JP2006131519A (ja) * | 2004-11-04 | 2006-05-25 | Idemitsu Kosan Co Ltd | 縮合環含有化合物及びそれを用いた有機エレクトロルミネッセンス素子 |
JP5266514B2 (ja) * | 2005-03-29 | 2013-08-21 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子 |
WO2011014039A1 (en) * | 2009-07-31 | 2011-02-03 | Rohm And Haas Electronic Materials Korea Ltd. | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
JP5120398B2 (ja) * | 2010-03-04 | 2013-01-16 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子及び表示装置 |
KR20120020818A (ko) * | 2010-08-31 | 2012-03-08 | 롬엔드하스전자재료코리아유한회사 | 신규한 유기 전자재료용 화합물 및 이를 포함하는 유기 전계 발광 소자 |
KR101477614B1 (ko) * | 2010-09-17 | 2014-12-31 | 롬엔드하스전자재료코리아유한회사 | 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 전계 발광 소자 |
KR20120038060A (ko) * | 2010-10-13 | 2012-04-23 | 롬엔드하스전자재료코리아유한회사 | 신규한 유기 전자재료용 화합물 및 이를 포함하는 유기 전계 발광 소자 |
KR20120109744A (ko) * | 2011-03-25 | 2012-10-09 | 롬엔드하스전자재료코리아유한회사 | 신규한 유기 전자재료용 화합물 및 이를 포함하는 유기 전계 발광 소자 |
KR20120116272A (ko) * | 2011-04-12 | 2012-10-22 | 롬엔드하스전자재료코리아유한회사 | 신규한 유기 전자재료용 화합물 및 이를 포함하는 유기 전계 발광 소자 |
KR102008134B1 (ko) * | 2011-05-30 | 2019-08-09 | 롬엔드하스전자재료코리아유한회사 | 신규한 유기 전자재료용 화합물 및 이를 포함하는 유기 전계 발광 소자 |
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- 2014-03-17 CN CN201410231701.6A patent/CN104292218A/zh active Pending
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TWI631109B (zh) | 2018-08-01 |
TW201441206A (zh) | 2014-11-01 |
CN104292218A (zh) | 2015-01-21 |
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