JP2005533341A - トリアリールメタンを主成分とする電荷輸送組成物およびその電子デバイスにおける使用 - Google Patents
トリアリールメタンを主成分とする電荷輸送組成物およびその電子デバイスにおける使用 Download PDFInfo
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- JP2005533341A JP2005533341A JP2004520121A JP2004520121A JP2005533341A JP 2005533341 A JP2005533341 A JP 2005533341A JP 2004520121 A JP2004520121 A JP 2004520121A JP 2004520121 A JP2004520121 A JP 2004520121A JP 2005533341 A JP2005533341 A JP 2005533341A
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- biphenyl
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- 239000000203 mixture Substances 0.000 title claims abstract description 80
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 52
- 125000003118 aryl group Chemical group 0.000 claims description 45
- 125000001072 heteroaryl group Chemical group 0.000 claims description 33
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
- 235000010290 biphenyl Nutrition 0.000 claims description 26
- 239000004305 biphenyl Substances 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 20
- 125000005842 heteroatom Chemical group 0.000 claims description 17
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 125000004076 pyridyl group Chemical class 0.000 claims description 11
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 10
- 125000000732 arylene group Chemical group 0.000 claims description 9
- 150000002430 hydrocarbons Chemical group 0.000 claims description 9
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- -1 siloxanes Chemical class 0.000 claims description 8
- 125000005549 heteroarylene group Chemical group 0.000 claims description 7
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims description 6
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims description 6
- 239000012964 benzotriazole Substances 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 125000004450 alkenylene group Chemical group 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000004419 alkynylene group Chemical group 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 150000004982 aromatic amines Chemical group 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- 125000004474 heteroalkylene group Chemical group 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- GMACPFCYCYJHOC-UHFFFAOYSA-N [C].C Chemical group [C].C GMACPFCYCYJHOC-UHFFFAOYSA-N 0.000 claims 2
- 150000004756 silanes Chemical class 0.000 claims 2
- 239000010410 layer Substances 0.000 description 91
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 56
- 150000001875 compounds Chemical class 0.000 description 47
- 239000000463 material Substances 0.000 description 41
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 31
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 23
- 239000007787 solid Substances 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 239000012044 organic layer Substances 0.000 description 21
- 230000005525 hole transport Effects 0.000 description 19
- 238000000034 method Methods 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 11
- 150000001299 aldehydes Chemical class 0.000 description 11
- 229910052751 metal Inorganic materials 0.000 description 11
- 239000002184 metal Substances 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- CIPVVROJHKLHJI-UHFFFAOYSA-N n,n-diethyl-3-methylaniline Chemical compound CCN(CC)C1=CC=CC(C)=C1 CIPVVROJHKLHJI-UHFFFAOYSA-N 0.000 description 9
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 8
- 239000012153 distilled water Substances 0.000 description 8
- 239000010408 film Substances 0.000 description 8
- 229910052741 iridium Inorganic materials 0.000 description 8
- 150000002739 metals Chemical class 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 125000004429 atom Chemical group 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000004215 Carbon black (E152) Substances 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 6
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 6
- 238000005266 casting Methods 0.000 description 6
- 239000000356 contaminant Substances 0.000 description 6
- 239000003480 eluent Substances 0.000 description 6
- 229930195733 hydrocarbon Natural products 0.000 description 6
- 239000012535 impurity Substances 0.000 description 6
- 239000003446 ligand Substances 0.000 description 6
- 230000007935 neutral effect Effects 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000002243 precursor Substances 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 238000010129 solution processing Methods 0.000 description 6
- 239000006228 supernatant Substances 0.000 description 6
- 239000010409 thin film Substances 0.000 description 6
- 235000019439 ethyl acetate Nutrition 0.000 description 5
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- ZRYZBQLXDKPBDU-UHFFFAOYSA-N 4-bromobenzaldehyde Chemical compound BrC1=CC=C(C=O)C=C1 ZRYZBQLXDKPBDU-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 239000002800 charge carrier Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 238000005401 electroluminescence Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000007646 gravure printing Methods 0.000 description 3
- 238000007641 inkjet printing Methods 0.000 description 3
- 125000002524 organometallic group Chemical group 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- 238000007650 screen-printing Methods 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000002207 thermal evaporation Methods 0.000 description 3
- 239000003039 volatile agent Substances 0.000 description 3
- VXWBQOJISHAKKM-UHFFFAOYSA-N (4-formylphenyl)boronic acid Chemical compound OB(O)C1=CC=C(C=O)C=C1 VXWBQOJISHAKKM-UHFFFAOYSA-N 0.000 description 2
- YDUVZTACEKAXTE-UHFFFAOYSA-N 1,3,5,7-tetraphenyladamantane Chemical compound C1C(C2)(C=3C=CC=CC=3)CC(C3)(C=4C=CC=CC=4)CC1(C=1C=CC=CC=1)CC23C1=CC=CC=C1 YDUVZTACEKAXTE-UHFFFAOYSA-N 0.000 description 2
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 2
- UDGYLQTZGJGKPC-UHFFFAOYSA-N 2-(4-fluorophenyl)-5-(trifluoromethyl)pyridine Chemical compound C1=CC(F)=CC=C1C1=CC=C(C(F)(F)F)C=N1 UDGYLQTZGJGKPC-UHFFFAOYSA-N 0.000 description 2
- FSEXLNMNADBYJU-UHFFFAOYSA-N 2-phenylquinoline Chemical compound C1=CC=CC=C1C1=CC=C(C=CC=C2)C2=N1 FSEXLNMNADBYJU-UHFFFAOYSA-N 0.000 description 2
- UOQXIWFBQSVDPP-UHFFFAOYSA-N 4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1 UOQXIWFBQSVDPP-UHFFFAOYSA-N 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- UTGQNNCQYDRXCH-UHFFFAOYSA-N N,N'-diphenyl-1,4-phenylenediamine Chemical compound C=1C=C(NC=2C=CC=CC=2)C=CC=1NC1=CC=CC=C1 UTGQNNCQYDRXCH-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 240000007817 Olea europaea Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- XZCJVWCMJYNSQO-UHFFFAOYSA-N butyl pbd Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=NN=C(C=2C=CC(=CC=2)C=2C=CC=CC=2)O1 XZCJVWCMJYNSQO-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
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- 239000013058 crude material Substances 0.000 description 2
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- JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 description 2
- 238000004770 highest occupied molecular orbital Methods 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- 229910003455 mixed metal oxide Inorganic materials 0.000 description 2
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- 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 2
- 229910052697 platinum Inorganic materials 0.000 description 2
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- 238000010791 quenching Methods 0.000 description 2
- 230000006798 recombination Effects 0.000 description 2
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- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- YWDUZLFWHVQCHY-UHFFFAOYSA-N 1,3,5-tribromobenzene Chemical compound BrC1=CC(Br)=CC(Br)=C1 YWDUZLFWHVQCHY-UHFFFAOYSA-N 0.000 description 1
- PMJKKMPWMNQYMY-UHFFFAOYSA-N 2-[3,5,7-tris(2-formylphenyl)-1-adamantyl]benzaldehyde Chemical compound C12(CC3(CC(CC(C1)(C3)C3=CC=CC=C3C=O)(C2)C2=CC=CC=C2C=O)C2=CC=CC=C2C=O)C2=CC=CC=C2C=O PMJKKMPWMNQYMY-UHFFFAOYSA-N 0.000 description 1
- JFZJMSDDOOAOIV-UHFFFAOYSA-N 2-chloro-5-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC=C(Cl)N=C1 JFZJMSDDOOAOIV-UHFFFAOYSA-N 0.000 description 1
- OXPDQFOKSZYEMJ-UHFFFAOYSA-N 2-phenylpyrimidine Chemical compound C1=CC=CC=C1C1=NC=CC=N1 OXPDQFOKSZYEMJ-UHFFFAOYSA-N 0.000 description 1
- ZLDMZIXUGCGKMB-UHFFFAOYSA-N 3,5-dibromobenzaldehyde Chemical compound BrC1=CC(Br)=CC(C=O)=C1 ZLDMZIXUGCGKMB-UHFFFAOYSA-N 0.000 description 1
- CATOVPRCMWIZLR-UHFFFAOYSA-N 3-ethenylbenzaldehyde Chemical compound C=CC1=CC=CC(C=O)=C1 CATOVPRCMWIZLR-UHFFFAOYSA-N 0.000 description 1
- NEAZMARKCJKUMF-QGZVFWFLSA-N 3-methyl-5-[7-[4-[(4r)-4-methyl-4,5-dihydro-1,3-oxazol-2-yl]phenoxy]heptyl]-1,2-oxazole Chemical compound C[C@@H]1COC(C=2C=CC(OCCCCCCCC=3ON=C(C)C=3)=CC=2)=N1 NEAZMARKCJKUMF-QGZVFWFLSA-N 0.000 description 1
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 1
- KBXXZTIBAVBLPP-UHFFFAOYSA-N 4-[[4-(diethylamino)-2-methylphenyl]-(4-methylphenyl)methyl]-n,n-diethyl-3-methylaniline Chemical compound CC1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)N(CC)CC)C)C1=CC=C(C)C=C1 KBXXZTIBAVBLPP-UHFFFAOYSA-N 0.000 description 1
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- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- 0 CCN(CC)c1ccc(C(c(cc2)ccc2N(c2ccccc2)c(cc2)ccc2N(c2ccccc2)c2ccc(C(c3c(C)cc(*)cc3)c3ccc(*)cc3C)cc2)c(cc2)c(C)cc2N(CC)CC)c(C)c1 Chemical compound CCN(CC)c1ccc(C(c(cc2)ccc2N(c2ccccc2)c(cc2)ccc2N(c2ccccc2)c2ccc(C(c3c(C)cc(*)cc3)c3ccc(*)cc3C)cc2)c(cc2)c(C)cc2N(CC)CC)c(C)c1 0.000 description 1
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- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
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- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
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- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 241001126918 Sycon Species 0.000 description 1
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- 229910052768 actinide Inorganic materials 0.000 description 1
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- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 1
- XEPMXWGXLQIFJN-UHFFFAOYSA-K aluminum;2-carboxyquinolin-8-olate Chemical compound [Al+3].C1=C(C([O-])=O)N=C2C(O)=CC=CC2=C1.C1=C(C([O-])=O)N=C2C(O)=CC=CC2=C1.C1=C(C([O-])=O)N=C2C(O)=CC=CC2=C1 XEPMXWGXLQIFJN-UHFFFAOYSA-K 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 150000003851 azoles Chemical class 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
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Images
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Abstract
Description
本件出願は、2002年7月10日に出願された米国仮特許出願第60/394767号ならびに2003年3月28日に出願された米国仮特許出願第60/458277号の優先権の利益を主張するものである。
Ar1は、出現するごとに同一または異なることが可能であり、かつアリールとヘテロアリールとから選択され、
R1は、出現するごとに同一または異なることが可能であり、かつHと、アルキルと、ヘテロアルキルと、アリールと、ヘテロアリールと、アリールアルキレンと、ヘテロアリールアルキレンと、CnHaFbと、C6HcFdとから選択されるか、あるいは隣接するR1基が結合して5員環または6員環を形成することが可能であり、
Xは、出現するごとに同一または異なることが可能であり、かつR1と、アルケニルと、アルキニルと、N(R1)2と、OR1と、OCnHaFbと、OC6HcFdと、ハロゲン化物と、NO2と、OHと、CNと、COOR1とから選択され、
nは整数であり、
a、b、cおよびdは0であるか、a+b=2n+1かつc+d=5になるような整数である。
R2は、出現するごとに同一または異なり、かつアリーレンと、ヘテロアリーレンと、アリーレンアルキレンと、ヘテロアリーレンアルキレンとから選択され、但し、R2がアリーレンアルキレンまたはヘテロアリーレンアルキレンの場合に、アリーレン末端がトリアリールメタン炭素に結合され、
Qは、単結合と多価基とから選択され、
mは少なくとも2に等しい整数であり、
pは0または1であり、但し、pが0の場合にQはアリーレンまたはヘテロアリーレンである多価基であり、
Ar1、R1、a〜d、nは上記にて定義したとおりである。
本発明は、本発明の電荷輸送組成物のうちの少なくとも1種を含む電子デバイスにも関するものである。電荷輸送組成物は、光活性層と電極1個との間に位置する独立した層の状態にすることができる。あるいは、本発明の電荷輸送組成物を光活性層に入れてもよい。一般的なデバイス構造を図7に示す。デバイス100はアノード層110とカソード層160とを有する。アノードに隣接しているのは正孔輸送材料を含む層120である。カソードに隣接しているのは電子輸送材料および/またはアンチクエンチング材料を含む層140である。正孔輸送層と電子輸送層および/またはアンチクエンチング層との間が光活性層130である。任意に、これらのデバイスではカソードの隣りに別の電子輸送層150が用いられることが多い。層120、130、140、150については、個別ならびに総称として活性層と呼ぶ。
本実施例は、図3に示されるトリアリールメタン正孔輸送組成物の調製について説明するものである。
上記の手順におけるp−フルオロベンズアルデヒドを同等の適当なアルデヒドに代えて、同様にして他のトリアリールメタン化合物を生成した。
化合物I(a):収率58%;MPt113℃;1H nmr:7.1(t);7.0(t);6.9(d);6.4(d);6.35(s);6.28(d);5.37(s);3.15(q);1.97(s);1.0(t)
化合物I(b):収率64%;MPt167℃;1H nmr:7.45(d);7.1(d);6.4(m);6.35(m);5.45(s);3.23(q);2.02(s);1.05(t)
化合物I(c):収率79%;MPt161℃;1H nmr:8.10(d);7.16(d);6.4(m);6.35(m);5.50(s);3.23(q);2.02(s);1.05(t)
化合物I(d):収率62%;MPt143℃;1H nmr:7.38(d);6.97(d);6.54(m);6.42(m);5.47(s);3.35(q);2.12(s);1.15(t)
化合物I(e):収率48%;MPt96℃;1H nmr: 6.88(d);6.71(d);6.5(d);6.41(m);6.3(m);5.35(s);3.23(q);2.02(s);1.05(t)
化合物I(g):収率3%;MPt.155℃;1H nmr:6.95(d);6.72(d);6.62(d);6.55(m);6.45(m);5.45(s);4.64(s);3.33(q);2.12(s);1.15(t)
化合物I(h):収率14%;MPt.139℃;1H nmr:6.80(d);6.6(d);6.5(m);6.38(m);5.33(s);2.80(s);2.06(s)
化合物I(i):収率40%;MPt.163℃;1H nmr:7.16(d);6.87(d);6.51(d);6.40(s);6.32(d);5.38(s);3.23(q);2.02(s);1.21(s);1.05(t)
化合物I(j):収率59%;MPt.159℃;1H nmr:7.51(d);7.38(d);7.33(t);7.22(t)7.05(d)6.54(d);6.43(s);6.35(d);5.45(s);3.23(q);2.02(s);1.05(t)
化合物I(k):収率7%;MPt.198℃;1H nmr:6.70(d);6.42(m);5.68(s);3.23(q);2.02(s);1.05(t);19F nmr:−140.6(m);−158.0(m);−163.0(m)
化合物I(l):収率98%;MPt.122℃;1H nmr:7.18(d);7.13(s);7.00(t);6.85(d);6.42(d);6.39(s);6.30(m);5.35(s);3.23(q);2.02(s);1.05(t)
化合物I(m):収率68%;MPt. 147℃;1H nmr:7.30(d);6.96(d);6.32(m);6.24(m);5.34(s);3.13(q);1.95(s);1.00(t);19F nmr:−62.6(s)
化合物I(n):収率57%;MPt.150℃;1H nmr:7.20(m);6.88(m);6.4(m);6.35(m);5.38(s);3.23(q);2.02(s);1.05(t);19F nmr:−112.6(s)
化合物I(o):収率41%;MPt.135℃;1H nmr:8.58(d);7.79(d);7.6(m);7.1(d);6.54(d);6.42(s);6.35(d);5.47(s);3.23(q);2.02(s);1.05(t)
化合物I(p):収率43%;MPt.111℃;1H nmr:7.50(s);6.4(m);6.35(m);5.50(s);3.23(q);2.02(s);1.05(t);19F nmr:−108.1(s);−108.5(s)。
本実施例は、図5の化合物II(c)である複数のトリアリールメタン基を有する正孔輸送化合物の調製について説明するものである。
(非特許文献5)に準じて1,3,5,7−テトラフェニルアダマンタンを調製した。
マグネチックスターラーバーと、ディーンスタークトラップと、冷却器と、窒素注入口とを取りつけた100mL容の一首丸底フラスコに、1,3,5,7−アダマンタンテトラキスベンズアルデヒド(0.55g、1.0mmol)と、n−ブタノール60mLと、濃HCl20mLと、N,N−ジエチル−m−トルアミド(0.666g、4.08mmol)とを仕込んだ。反応混合物を還流状態で24時間加熱した後、さらに16時間にわたって水を共沸蒸留した。残った緑色の溶液をロータリーエバポレータで濃縮し、メチレンクロリド150mLに溶解させ、水150mLで洗浄した。飽和炭酸水素ナトリウム水溶液を加えて水性層をpH8に調整した。この混合物を振盪し、層を分離させ、有機層をMgSO4上で乾燥させた後、ロータリーエバポレータで濃縮して茶色でガラス質の固体1.4958gを得た。シリカゲル上でのフラッシュクロマトグラフィによる精製(CH2Cl2中2.5%i−PrOH)により、黄褐色でガラス質の固体0.8977gが得られた。
本実施例は、図6に式IV(a)として示すイリジウムエレクトロルミネッセンス錯体の調製について説明するものである。
使用した大まかな手順は、(非特許文献6)に説明されていた。脱気水200mlと、炭酸カリウム20gと、1,2−ジメトキシエタン150mlと、Pd(PPh3)40.5gと、2−クロロ−5−トリフルオロメチルピリジン0.05molと、4−フルオロフェニルボロン酸0.05molとの混合物を16〜30時間還流(80〜90℃)した。このようにして得られる反応混合物を水300mlで希釈し、CH2Cl2(2×100ml)で抽出した。混合有機層をMgSO4上で乾燥させ、真空により溶媒を除去した。この液体生成物を真空分留で精製した。固体材料をヘキサンから再結晶化させた。単離した材料の典型的な純度は98%を超えていた。
IrCl3・nH2O(54%Ir;508mg)と、上記にて得られた2−(4−フルオロフェニル)−5−トリフルオロメチルピリジン(2.20g)と、AgOCOCF3(1.01g)と、水(1mL)との混合物を、温度を徐々に(30分間)185℃(油浴)まで上げながらN2流下で強く攪拌した。185〜190℃で2時間経過後、混合物が固化した。この混合物を室温まで冷ました。抽出物の色がなくなるまで、固体をジクロロメタンで抽出した。この混合ジクロロメタン溶液を短いシリカカラムで濾過し、脱水した。残渣にメタノール(50mL)を添加した後、フラスコを−10℃で一晩保持した。トリス−シクロメタル化錯体すなわち化合物IVaの黄色の沈殿物を分離し、メタノールで洗浄し、真空下で乾燥させた。収率1.07g(82%)。その温かい溶液を1,2−ジクロロエタン中でゆっくりと冷却することで、錯体のX線品質(X−Ray quality)の結晶が得られた。
本実施例は、本発明の電荷輸送組成物を用いたOLEDの製造について説明するものである。
本実施例は、図3の化合物I(q)の調製について説明するものである。
本実施例は、図5の化合物II(d)の調製について説明するものである。
本実施例は、図3の化合物I(r)の調製について説明するものである。
本実施例は、図3の化合物I(s)の調製について説明するものである。
本実施例は、図5の化合物II(e)の調製について説明するものである。
本実施例は、図5の化合物II(f)の調製について説明するものである。
本実施例は、以下に示す反応スキームを利用した、図3の化合物I(t)の調製について説明するものである。
窒素雰囲気下、40mL容のバイアルに、4−ブロモベンズアルデヒド(3.478g、0.0188mol)と、カルバゾール(3.013g、0.0179mol)と、Pd(OAc)2(0.0402g、1.79×10−4mol)と、P(t−Bu)3(0.1086g、5.37×10−4mol)と、K2CO3(7.422g、0.0537mol)と、o−キシレン20mLとを仕込んだ。この反応混合物を2日間加熱(100℃)した。得られる混合物を、ヘキサンに続いて25%EtOAc/ヘキサン、最後にヘキサンを用いてシリカのプラグ(plug of silica)で濾過した。揮発性物質を蒸発させて淡い黄色の固体を得て、これを高温のMeOH(20mL)およびヘキサン(20mL)で洗浄した。所望の生成物を白色の粉末として収率29%(1.406g)で単離した。
窒素雰囲気下、50mL容の三首フラスコに、前駆体化合物A(1.000g、5.98mmol)と、N,N−ジエチル−m−トルイジン(2.12mL、11.9mmol)と、濃HCl(1mL)と、EtOH(2mL)とを仕込んだ。得られる混合物を3日間還流した。室温まで冷ました後、溶液をH2O25mLで希釈し、50%NaOH溶液を用いてpH9に調整した。ロータリーエバポレータで揮発性物質を除去し、生成物をクロマトグラフィ(7%EtOAc/ヘキサン)で精製して0.91g(収率26%)とした。
本実施例は、以下に示す反応スキームを利用した、図5の化合物II(g)の調製について説明するものである。
本実施例は、以下に示す反応スキームを利用した、図5の化合物II(h)の調製について説明するものである。
C76H88N6についての分析計算値:C,84.09;H、8.17;N、7.74。実測値:C,84.19、H、8.37、N、7.69。
Claims (47)
- 図1に示される式Iを有するトリアリールメタンを含む組成物であって、式中、
Ar1は、出現するごとに同一または異なることが可能であり、かつアリールとヘテロアリールとから選択され、
R1は、出現するごとに同一または異なり、かつHと、アルキルと、ヘテロアルキルと、アリールと、ヘテロアリールと、アリールアルキレンと、ヘテロアリールアルキレンと、CnHaFbと、C6HcFdとから選択されるか、あるいは隣接するR1基が結合して5員環または6員環を形成することが可能であり、
Xは、出現するごとに同一または異なることが可能であり、かつR1と、アルケニルと、アルキニルと、N(R1)2と、OR1と、OCnHaFbと、OC6HcFdと、CNと、COOR1と、ハロゲン化物と、NO2と、OHとから選択され、
nは1から12の整数であり、
a、b、cおよびdは、0であるか、a+b=2n+1かつc+d=5になるような整数であり、
但し、Fと、CnHaFbと、OCnHaFbと、C6HcFdと、OC6HcFdとから選択される少なくとも1個の置換基が芳香族基上にあることを特徴とする組成物。 - 前記トリアリールメタンが、図3の式I(f)、式I(k)、式I(m)、式I(n)、式I(p)から選択されることを特徴とする請求項1に記載の組成物。
- 図3の式I(i)、式I(j)、式I(l)、式I(o)、式I(q)、式I(r)、式I(s)、式I(t)から選択される組成物。
- 少なくとも2個のトリアリールメタン炭素を有し、図2の式IIを有する組成物であって、式中、
Ar1は、出現するごとに同一または異なり、かつアリールとヘテロアリールとから選択され、
R1は、出現するごとに同一または異なり、かつHと、アルキルと、ヘテロアルキルと、アリールと、ヘテロアリールと、アリールアルキレンと、ヘテロアリールアルキレンと、CnHaFbと、C6HcFdとから選択され、
R2は、出現するごとに同一または異なり、アリーレンと、ヘテロアリーレンと、アリーレンアルキレンと、ヘテロアリーレンアルキレンとから選択され、但し、R2がアリーレンアルキレンまたはヘテロアリーレンアルキレンの場合にアリーレン末端がトリアリールメタン炭素に結合され、
Qは、単結合と多価基とから選択され、
mは少なくとも2に等しい整数であり、
pは0または1であり、但し、pが0の場合にQはアリーレンまたはヘテロアリーレンである多価基であることを特徴とする組成物。 - Qが、脂肪族基と、複素脂肪族基と、芳香族基と、複素芳香族基とから選択される、少なくとも2個の結合点を有する炭化水素基から選択されることを特徴とする請求項4に記載の組成物。
- Qが、アルキレン基と、ヘテロアルキレン基と、アルケニレン基と、ヘテロアルケニレン基と、アルキニレン基と、ヘテロアルキニレン基とから選択されることを特徴とする請求項5に記載の組成物。
- Qが、単環式芳香族基と、多環式芳香族基と、縮合環芳香族基と、単環式複素芳香族基と、多環式芳香族基と、縮合環芳香族基と、アリールアミンと、シランと、シロキサンとから選択されることを特徴とする請求項4に記載の組成物。
- Qが、図4の式III(a)〜式III(h)から選択されることを特徴とする請求項4に記載の組成物。
- Ar1が、フェニルと、置換フェニルと、ビフェニルと、置換ビフェニルとから選択されることを特徴とする請求項4に記載の組成物。
- Ar1が、アルキルと、ヘテロアルキルと、アリールと、ヘテロアリールと、アリールアルキレンと、ヘテロアリールアルキレンと、CnHaFbと、C6HcFdとから選択される少なくとも1個の置換基を有する置換フェニルおよび置換ビフェニルから選択され、
a、b、cおよびdは0であるか、a+b=2n+1かつc+d=5になるような整数であり、
nは整数であることを特徴とする請求項9に記載の組成物。 - Ar1が、フェニルと、置換フェニルと、ビフェニルと、置換ビフェニルとから選択され、少なくとも1個の炭素原子がヘテロ原子で置換されることを特徴とする請求項4に記載の組成物。
- R2が、フェニルと、置換フェニルと、ビフェニルと、置換ビフェニルと、ピリジルと、置換ピリジルと、ビピリジルと、置換ビピリジルとから選択されることを特徴とする請求項4に記載の組成物。
- R2が、ヘテロアルキルと、アリールと、ヘテロアリールと、アリールアルキレンと、ヘテロアリールアルキレンと、CnHaFbと、C6HcFdとから選択される少なくとも1個の置換基を有する、置換フェニルと、置換ビフェニルと、置換ピリジルとから選択され、式中、
a、b、cおよびdは0であるか、a+b=2n+1かつc+d=5になるような整数であり、
nは整数であることを特徴とする請求項12に記載の組成物。 - 図5の式II(a)〜式II(h)から選択される請求項4に記載の組成物。
- 図1に示される式Iを有するトリアリールメタン誘導体を含む層を少なくとも1層含む電子デバイスであって、式中、
Ar1は、出現するごとに同一または異なることが可能であり、かつアリールとヘテロアリールとから選択され、
R1は、出現するごとに同一または異なり、かつHと、アルキルと、ヘテロアルキルと、アリールと、ヘテロアリールと、アリールアルキレンと、ヘテロアリールアルキレンと、アリールアルキレンと、ヘテロアリールアルキレンと、CnHaFbと、C6HcFdとから選択されるか、あるいは隣接するR1基が結合して5員環または6員環を形成することが可能であり、
Xは、出現するごとに同一または異なることが可能であり、かつR1と、アルケニルと、アルキニルと、N(R1)2と、OR1と、OCnHaFbと、OC6HcFdと、CNと、COOR1と、ハロゲン化物と、NO2と、OHとから選択され、
nは1から12の整数であり、
a、b、cおよびdは0であるか、a+b=2n+1かつc+d=5になるような整数であり、
但し、X5Ar1がp−メチルフェニレンの場合にR1はエチルではないことを特徴とする電子デバイス。 - Ar1が、フェニルと、置換フェニルと、ビフェニルと、置換ビフェニルとから選択されることを特徴とする請求項15に記載の電子デバイス。
- Ar1が、アルキルと、ヘテロアルキルと、アリールと、ヘテロアリールと、アリールアルキレンと、ヘテロアリールアルキレンと、CnHaFbと、C6HcFdとから選択される少なくとも1個の置換基を有する、置換フェニルおよび置換ビフェニルから選択され、式中、
a、b、cおよびdは0であるか、a+b=2n+1かつc+d=5になるような整数であり、
nは整数であることを特徴とする請求項16に記載のデバイス。 - Ar1が、フェニルと、置換フェニルと、ビフェニルと、置換ビフェニルとから選択され、少なくとも1個の炭素原子がヘテロ原子で置換されることを特徴とする請求項15に記載のデバイス。
- X5Ar1が、フェニルと、置換フェニルと、ビフェニルと、置換ビフェニルと、ピリジルと、置換ピリジルと、ビピリジルと、置換ビピリジルとから選択されるAr1を有することを特徴とする請求項15に記載のデバイス。
- Ar1が、ヘテロアルキルと、アリールと、ヘテロアリールと、アリールアルキレンと、ヘテロアリールアルキレンと、CnHaFbと、C6HcFdとから選択される少なくとも1個の置換基を有する、置換フェニルと、置換ビフェニルと、置換ピリジルとから選択され、式中、
a、b、cおよびdは0であるか、a+b=2n+1かつc+d=5になるような整数であり、
nは整数であることを特徴とする請求項19に記載のデバイス。 - Fと、CnHaFbと、OCnHaFbと、C6HcFdと、OC6HcFdとから選択される少なくとも1個の置換基がアリール環上にあり、式中、
a、b、cおよびdは0であるか、a+b=2n+1かつc+d=5になるような整数であり、
nは整数であることを特徴とする請求項15に記載のデバイス。 - 少なくとも1個のX基が、Fと、CnHaFbと、OCnHaFbと、C6HcFdと、OC6HcFdとから選択され、式中、
a、b、cおよびdは0であるか、a+b=2n+1かつc+d=5になるような整数であり、
nは整数であることを特徴とする請求項15に記載のデバイス。 - 前記トリアリールメタン誘導体が図3の式I(a)〜式I(t)から選択されることを特徴とする請求項15に記載の電子デバイス。
- 少なくとも2個のトリアリールメタン炭素を有する電荷輸送組成物を含む層を少なくとも1層含む電子デバイスであって、前記組成物が図2の式IIを有し、式中、
Ar1は、出現するごとに同一または異なることが可能であり、かつアリールとヘテロアリールとから選択され、
R1は、出現するごとに同一または異なり、かつHと、アルキルと、ヘテロアルキルと、アリールと、ヘテロアリールと、アリールアルキレンと、ヘテロアリールアルキレンと、CnHaFbと、C6HcFdとから選択され、
R2は、出現するごとに同一または異なり、かつアリーレンと、ヘテロアリーレンと、アリーレンアルキレンと、ヘテロアリーレンアルキレンとから選択され、但し、R2がアリーレンアルキレンまたはヘテロアリーレンアルキレンの場合にアリーレン末端がトリアリールメタン炭素に結合され、
Qは、単結合と多価基とから選択され、
mは少なくとも2に等しい整数であり、
pは0または1であり、但し、pが0の場合にQはアリーレンまたはヘテロアリーレンである多価基であることを特徴とする電子デバイス。 - Qが、脂肪族基と、複素脂肪族基と、芳香族基と、複素芳香族基とから選択される、少なくとも2個の結合点を有する炭化水素基から選択されることを特徴とする請求項24に記載のデバイス。
- Qが、アルキル基と、ヘテロアルキル基と、アルケニル基と、ヘテロアルケニル基と、アルキニル基と、ヘテロアルキニル基とから選択されることを特徴とする請求項25に記載のデバイス。
- Qが、単環式芳香族基と、多環式芳香族基と、縮合環芳香族基と、単環式複素芳香族基と、多環式芳香族基と、縮合環芳香族基と、アリールアミンと、シランと、シロキサンとから選択されることを特徴とする請求項24に記載のデバイス。
- Qが図4の式III(a)〜式III(h)から選択されることを特徴とする請求項24に記載のデバイス。
- Ar1が、フェニルと、置換フェニルと、ビフェニルと、置換ビフェニルとから選択されることを特徴とする請求項24に記載のデバイス。
- Ar1が、アルキルと、ヘテロアルキルと、アリールと、ヘテロアリールと、アリールアルキレンと、ヘテロアリールアルキレンと、CnHaFbと、C6HcFdとから選択される少なくとも1個の置換基を有する、置換フェニルおよび置換ビフェニルから選択され、式中、
a、b、cおよびdは0であるか、a+b=2n+1かつc+d=5であるような整数であり、
nは整数であることを特徴とする請求項29に記載のデバイス。 - Ar1が、フェニルと、置換フェニルと、ビフェニルと、置換ビフェニルとから選択され、少なくとも1個の炭素原子がヘテロ原子で置換されることを特徴とする請求項24に記載のデバイス。
- R2が、フェニルと、置換フェニルと、ビフェニルと、置換ビフェニルと、ピリジルと、置換ピリジルと、ビピリジルと、置換ビピリジルとから選択されることを特徴とする請求項24に記載のデバイス。
- R2が、ヘテロアルキルと、アリールと、ヘテロアリールと、アリールアルキレンと、ヘテロアリールアルキレンと、CnHaFbと、C6HcFdとから選択される少なくとも1個の置換基を有する、置換フェニルと、置換ビフェニルと、置換ピリジルとから選択され、
a、b、cおよびdは0であるか、a+b=2n+1かつc+d=5になるような整数であり、
nは整数であることを特徴とする請求項32に記載のデバイス。 - 前記電荷輸送組成物が、図5の式II(a)〜式II(h)から選択されることを特徴とする請求項24に記載のデバイス。
- 少なくとも1個のN(R1)2が縮合芳香族環基であることを特徴とする請求項4に記載の組成物。
- 少なくとも1個のN(R1)2が、カルバゾールと、ベンゾジアゾールと、ベンゾトリアゾールとから選択されることを特徴とする請求項4に記載の組成物。
- 少なくとも1個のXが縮合複素芳香環基であることを特徴とする請求項36に記載のデバイス。
- 少なくとも1個のXが、N−カルバゾールと、ベンゾジアゾールと、ベンゾトリアゾールとから選択されることを特徴とする請求項37に記載のデバイス。
- 少なくとも1個のN(R1)2が縮合複素芳香環基であることを特徴とする請求項24に記載のデバイス。
- 少なくとも1個のN(R1)2が、カルバゾールと、ベンゾジアゾールと、ベンゾトリアゾールとから選択されることを特徴とする請求項39に記載のデバイス。
- 図1で示される式Iを有するトリアリールメタンを含む組成物であって、式中、
Ar1は、出現するごとに同一または異なることが可能であり、かつアリールとヘテロアリールとから選択され、
R1は、出現するごとに同一または異なり、かつHと、アルキルと、ヘテロアルキルと、アリールと、ヘテロアリールと、CnHaFbと、C6HcFdとから選択され、
nは1から12の整数であり、
a、b、cおよびdは、a+b=2n+1かつc+d=5であるような整数であり、
但し、Fと、CnHaFbと、OCnHaFbと、C6HcFdと、OC6HcFdとから選択される少なくとも1個の置換基が芳香族基上にあることを特徴とする組成物。 - 前記トリアリールメタンが図3の式I(a)〜式I(p)から選択されることを特徴とする請求項41に記載の組成物。
- 図2の式IIから選択される組成物であって、式中、
Qは、単結合と多価基とから選択され、
mは2から10の整数であり、
Ar1は、出現するごとに同一または異なることが可能であり、かつアリールとヘテロアリールとから選択され、
R1は、出現するごとに同一または異なり、かつHと、アルキルと、ヘテロアルキルと、アリールと、ヘテロアリールと、CnHaFbと、C6HcFdとから選択されることを特徴とする組成物。 - Qが、図4の式III(a)〜式III(h)から選択されることを特徴とする請求項43に記載の組成物。
- 図5の式II(a)、式II(b)および式II(c)から選択される請求項43に記載の組成物。
- 請求項41〜45のいずれか一項に記載の電荷輸送組成物を含む層を少なくとも1層含むことを特徴とする電子デバイス。
- 前記デバイスが、発光ダイオード、発光電気化学セルまたは光検出器であることを特徴とする請求項41〜45のいずれか一項に記載の電子デバイス。
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2003
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- 2003-07-09 JP JP2004520125A patent/JP2005533343A/ja active Pending
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- 2003-07-09 CN CNA038164620A patent/CN1668616A/zh active Pending
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- 2003-07-09 CA CA002492689A patent/CA2492689A1/en not_active Abandoned
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- 2003-07-09 JP JP2004520121A patent/JP2005533341A/ja active Pending
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- 2003-12-08 US US10/612,704 patent/US7399432B2/en not_active Expired - Fee Related
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2005
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2006
- 2006-04-21 HK HK06104776.6A patent/HK1084775A1/xx not_active IP Right Cessation
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2007
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2009
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2011
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JP2013057052A (ja) * | 2011-04-21 | 2013-03-28 | Dainippon Printing Co Ltd | 色材、及びその製造方法 |
WO2017145627A1 (ja) * | 2016-02-25 | 2017-08-31 | Dic株式会社 | 化合物及びカラーフィルタ |
JP6255634B1 (ja) * | 2016-02-25 | 2018-01-10 | Dic株式会社 | 化合物及びカラーフィルタ |
JP2020500954A (ja) * | 2016-11-01 | 2020-01-16 | ミリケン・アンド・カンパニーMilliken & Company | 洗濯ケア組成物における青味剤としてのロイコポリマー |
JP2019099795A (ja) * | 2017-11-29 | 2019-06-24 | キヤノン株式会社 | 色素化合物及び感熱転写記録用シート |
US11958978B2 (en) | 2017-11-29 | 2024-04-16 | Canon Kabuskiki Kaisha | Coloring compound and thermal transfer recording sheet |
JP7484189B2 (ja) | 2020-01-29 | 2024-05-16 | 富士フイルムビジネスイノベーション株式会社 | トリフェニルメタン化合物の製造方法 |
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