JP4880079B2 - 電子写真用感光体 - Google Patents
電子写真用感光体 Download PDFInfo
- Publication number
- JP4880079B2 JP4880079B2 JP2011122246A JP2011122246A JP4880079B2 JP 4880079 B2 JP4880079 B2 JP 4880079B2 JP 2011122246 A JP2011122246 A JP 2011122246A JP 2011122246 A JP2011122246 A JP 2011122246A JP 4880079 B2 JP4880079 B2 JP 4880079B2
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- JP
- Japan
- Prior art keywords
- polycarbonate resin
- substituted
- tert
- represented
- photoreceptor
- 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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- 108091008695 photoreceptors Proteins 0.000 title claims description 62
- 229920005668 polycarbonate resin Polymers 0.000 claims description 64
- 239000004431 polycarbonate resin Substances 0.000 claims description 64
- -1 p-terphenyl compound Chemical class 0.000 claims description 40
- 229930184652 p-Terphenyl Natural products 0.000 claims description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- XJKSTNDFUHDPQJ-UHFFFAOYSA-N 1,4-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=C(C=2C=CC=CC=2)C=C1 XJKSTNDFUHDPQJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000010410 layer Substances 0.000 description 77
- 239000003795 chemical substances by application Substances 0.000 description 35
- 239000000049 pigment Substances 0.000 description 28
- 229920005989 resin Polymers 0.000 description 27
- 239000011347 resin Substances 0.000 description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 150000001875 compounds Chemical class 0.000 description 24
- 239000000243 solution Substances 0.000 description 17
- 238000012546 transfer Methods 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 239000011230 binding agent Substances 0.000 description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 239000000463 material Substances 0.000 description 11
- 230000035945 sensitivity Effects 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 10
- 239000003963 antioxidant agent Substances 0.000 description 9
- 235000006708 antioxidants Nutrition 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 239000000654 additive Substances 0.000 description 8
- 239000004611 light stabiliser Substances 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 229910052782 aluminium Inorganic materials 0.000 description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- SJHHDDDGXWOYOE-UHFFFAOYSA-N oxytitamium phthalocyanine Chemical compound [Ti+2]=O.C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 SJHHDDDGXWOYOE-UHFFFAOYSA-N 0.000 description 7
- 239000011241 protective layer Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 6
- 230000003078 antioxidant effect Effects 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 6
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 5
- 239000004014 plasticizer Substances 0.000 description 5
- QGMMWGLDOBFHTL-UHFFFAOYSA-N 1,4-bis(4-iodophenyl)benzene Chemical group C1=CC(I)=CC=C1C1=CC=C(C=2C=CC(I)=CC=2)C=C1 QGMMWGLDOBFHTL-UHFFFAOYSA-N 0.000 description 4
- 229920002799 BoPET Polymers 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
- 239000004952 Polyamide Substances 0.000 description 4
- 238000002441 X-ray diffraction Methods 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 4
- 229910001873 dinitrogen Inorganic materials 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 4
- 229920002647 polyamide Polymers 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WUPHOULIZUERAE-UHFFFAOYSA-N 3-(oxolan-2-yl)propanoic acid Chemical compound OC(=O)CCC1CCCO1 WUPHOULIZUERAE-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 3
- 238000006887 Ullmann reaction Methods 0.000 description 3
- 239000006096 absorbing agent Substances 0.000 description 3
- 229910052980 cadmium sulfide Inorganic materials 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000006482 condensation reaction Methods 0.000 description 3
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 229940094933 n-dodecane Drugs 0.000 description 3
- 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 3
- 230000000704 physical effect Effects 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 229910052711 selenium Inorganic materials 0.000 description 3
- 239000011669 selenium Substances 0.000 description 3
- 239000002356 single layer Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000011787 zinc oxide Substances 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- UDHAWRUAECEBHC-UHFFFAOYSA-N 1-iodo-4-methylbenzene Chemical compound CC1=CC=C(I)C=C1 UDHAWRUAECEBHC-UHFFFAOYSA-N 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 2
- XJEVHMGJSYVQBQ-UHFFFAOYSA-N 2,3-dihydro-1h-inden-1-amine Chemical compound C1=CC=C2C(N)CCC2=C1 XJEVHMGJSYVQBQ-UHFFFAOYSA-N 0.000 description 2
- MRBKEAMVRSLQPH-UHFFFAOYSA-N 3-tert-butyl-4-hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1 MRBKEAMVRSLQPH-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- WOYOJAPRKMBKEU-UHFFFAOYSA-N N1-(2,3-Dihydro-1H-inden-5-yl)acetamide Chemical compound CC(=O)NC1=CC=C2CCCC2=C1 WOYOJAPRKMBKEU-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000004677 Nylon Substances 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 238000002679 ablation Methods 0.000 description 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 2
- 239000012964 benzotriazole Substances 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 description 2
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- KECKHZLCAKOGLW-UHFFFAOYSA-N n-(4-methylphenyl)-2,3-dihydro-1h-inden-5-amine Chemical compound C1=CC(C)=CC=C1NC1=CC=C(CCC2)C2=C1 KECKHZLCAKOGLW-UHFFFAOYSA-N 0.000 description 2
- 229920001778 nylon Polymers 0.000 description 2
- QUAMTGJKVDWJEQ-UHFFFAOYSA-N octabenzone Chemical compound OC1=CC(OCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 QUAMTGJKVDWJEQ-UHFFFAOYSA-N 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 239000002985 plastic film Substances 0.000 description 2
- 229920006255 plastic film Polymers 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 235000013824 polyphenols Nutrition 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 2
- 235000021286 stilbenes Nutrition 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 2
- WGVKWNUPNGFDFJ-DQCZWYHMSA-N β-tocopherol Chemical compound OC1=CC(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C WGVKWNUPNGFDFJ-DQCZWYHMSA-N 0.000 description 2
- POLSVAXEEHDBMJ-UHFFFAOYSA-N (2-hydroxy-4-octadecoxyphenyl)-phenylmethanone Chemical compound OC1=CC(OCCCCCCCCCCCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 POLSVAXEEHDBMJ-UHFFFAOYSA-N 0.000 description 1
- FHIDEWWHKSJPTK-UHFFFAOYSA-N (3,5-dinitrophenyl)-phenylmethanone Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC(C(=O)C=2C=CC=CC=2)=C1 FHIDEWWHKSJPTK-UHFFFAOYSA-N 0.000 description 1
- YRTPZXMEBGTPLM-UVTDQMKNSA-N (3z)-3-benzylidene-2-benzofuran-1-one Chemical compound C12=CC=CC=C2C(=O)O\C1=C/C1=CC=CC=C1 YRTPZXMEBGTPLM-UVTDQMKNSA-N 0.000 description 1
- ARVUDIQYNJVQIW-UHFFFAOYSA-N (4-dodecoxy-2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC(OCCCCCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 ARVUDIQYNJVQIW-UHFFFAOYSA-N 0.000 description 1
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- NMNSBFYYVHREEE-UHFFFAOYSA-N 1,2-dinitroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C([N+]([O-])=O)C([N+](=O)[O-])=CC=C3C(=O)C2=C1 NMNSBFYYVHREEE-UHFFFAOYSA-N 0.000 description 1
- IZUKQUVSCNEFMJ-UHFFFAOYSA-N 1,2-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1[N+]([O-])=O IZUKQUVSCNEFMJ-UHFFFAOYSA-N 0.000 description 1
- XVMIKRZPDSXBTP-UHFFFAOYSA-N 1,3-dibromobutan-2-one Chemical compound CC(Br)C(=O)CBr XVMIKRZPDSXBTP-UHFFFAOYSA-N 0.000 description 1
- WDCYWAQPCXBPJA-UHFFFAOYSA-N 1,3-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC([N+]([O-])=O)=C1 WDCYWAQPCXBPJA-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- VAIPJQIPFPRJKJ-UHFFFAOYSA-N 1,4-bis(4-bromophenyl)benzene Chemical group C1=CC(Br)=CC=C1C1=CC=C(C=2C=CC(Br)=CC=2)C=C1 VAIPJQIPFPRJKJ-UHFFFAOYSA-N 0.000 description 1
- ZBTMRBYMKUEVEU-UHFFFAOYSA-N 1-bromo-4-methylbenzene Chemical compound CC1=CC=C(Br)C=C1 ZBTMRBYMKUEVEU-UHFFFAOYSA-N 0.000 description 1
- HJRJRUMKQCMYDL-UHFFFAOYSA-N 1-chloro-2,4,6-trinitrobenzene Chemical compound [O-][N+](=O)C1=CC([N+]([O-])=O)=C(Cl)C([N+]([O-])=O)=C1 HJRJRUMKQCMYDL-UHFFFAOYSA-N 0.000 description 1
- YCANAXVBJKNANM-UHFFFAOYSA-N 1-nitroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2[N+](=O)[O-] YCANAXVBJKNANM-UHFFFAOYSA-N 0.000 description 1
- AHXBXWOHQZBGFT-UHFFFAOYSA-M 19631-19-7 Chemical compound N1=C(C2=CC=CC=C2C2=NC=3C4=CC=CC=C4C(=N4)N=3)N2[In](Cl)N2C4=C(C=CC=C3)C3=C2N=C2C3=CC=CC=C3C1=N2 AHXBXWOHQZBGFT-UHFFFAOYSA-M 0.000 description 1
- MEZZCSHVIGVWFI-UHFFFAOYSA-N 2,2'-Dihydroxy-4-methoxybenzophenone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1O MEZZCSHVIGVWFI-UHFFFAOYSA-N 0.000 description 1
- LWHDQPLUIFIFFT-UHFFFAOYSA-N 2,3,5,6-tetrabromocyclohexa-2,5-diene-1,4-dione Chemical group BrC1=C(Br)C(=O)C(Br)=C(Br)C1=O LWHDQPLUIFIFFT-UHFFFAOYSA-N 0.000 description 1
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 1
- SVPKNMBRVBMTLB-UHFFFAOYSA-N 2,3-dichloronaphthalene-1,4-dione Chemical compound C1=CC=C2C(=O)C(Cl)=C(Cl)C(=O)C2=C1 SVPKNMBRVBMTLB-UHFFFAOYSA-N 0.000 description 1
- LEWZOBYWGWKNCK-UHFFFAOYSA-N 2,3-dihydro-1h-inden-5-amine Chemical compound NC1=CC=C2CCCC2=C1 LEWZOBYWGWKNCK-UHFFFAOYSA-N 0.000 description 1
- ZXDDPOHVAMWLBH-UHFFFAOYSA-N 2,4-Dihydroxybenzophenone Chemical compound OC1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 ZXDDPOHVAMWLBH-UHFFFAOYSA-N 0.000 description 1
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- 125000004079 stearyl 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])C([H])([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
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- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
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- YKSGNOMLAIJTLT-UHFFFAOYSA-N violanthrone Chemical class C12=C3C4=CC=C2C2=CC=CC=C2C(=O)C1=CC=C3C1=CC=C2C(=O)C3=CC=CC=C3C3=CC=C4C1=C32 YKSGNOMLAIJTLT-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- G03G5/0679—Disazo dyes
- G03G5/0683—Disazo dyes containing polymethine or anthraquinone groups
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- G03G5/0696—Phthalocyanines
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Photoreceptors In Electrophotography (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyesters Or Polycarbonates (AREA)
Description
から選択されるp−ターフェニル化合物の1種以上と、一般式(I)
(式中、R1及びR2は同一でも異なってもよく水素原子、置換もしくは無置換のアルキル基または置換もしくは無置換のアリール基を表し、R1とR2が共同で環を形成しても良く、R3、R4、R5、R6、R7、R8、R9及びR10は同一でも異なってもよく水素原子、置換もしくは無置換のアルキル基、置換もしくは無置換のアリール基またはハロゲン原子を表し、pとqはモル組成分率を表し(qは0も含む)、pとqの比は式0≦q/p≦2を満足する関係にあり、Zは置換もしくは無置換の炭素数が1〜5のアルキレン基、置換もしくは無置換の4,4’−ビフェニレン基または一般式(II)
(式中、R11及びR12は同一でも異なってもよく水素原子、置換もしくは無置換のアルキル基または置換もしくは無置換のアリール基を表し、R11とR12が共同で環を形成しても良く、R13、R14、R15及びR16は同一でも異なってもよく水素原子、置換もしくは無置換のアルキル基、置換もしくは無置換のアリール基またはハロゲン原子を表し、rは0から3の整数を表す。)で表される2価基を表す。)で表されるポリカーボネート樹脂の1種以上を、p−ターフェニル化合物とポリカーボネート樹脂の質量比2:8ないし7:3の範囲内で含有する層を有する電子写真用感光体に関する。ただし、ポリカーボネート樹脂を1種のみ用いる場合においては、一般式(I)で表されるポリカーボネート樹脂の構造がR1及びR2がメチル基で、R3、R4、R5、R6、R7、R8、R9及びR10が水素原子で、qが0である場合を除く。
本発明の電子写真用感光体を使用することによって、感度、残留電位などの電子写真特性を向上させることができ、さらに高耐久性を満足することができる。
一般式(I)で示されるポリカーボネート樹脂の具体的な例として下記構造式で表されるものがあげられるが、本発明に使用されるポリカーボネート樹脂は、これらの具体例に限定されるものではない。ただし、一般式(I)で示されるポリカーボネート樹脂が、構造式(6)で表されるポリカーボネート樹脂のみからなる場合を除く。
第1図及び第2図は、導電性支持体1上に電荷発生物質を主成分として含有する電荷発生層2と電荷輸送物質及び結着樹脂を主成分として含有する電荷輸送層3の積層体よりなる感光層4を設けたものである。このとき、第3図、第4図及び第5図に示すように、感光層4は導電性支持体上に設けた電荷を調整するためのアンダーコート層5を介して設けても良く、最外層として保護層8を設けても良い。また本発明においては、第6図及び第7図に示すように電荷発生物質7を電荷輸送物質と結着樹脂を主成分とする層6中に溶解または分散させて成る感光層4を導電性支持体1上に直接、あるいはアンダーコート層5を介して設けても良い。
非特許文献2: 実験化学講座(第4版、日本化学会編)20、279〜318ページ
特許文献2: 特開昭53−95033号公報
特許文献3: 特開昭54−22834号公報
特許文献4: 特開昭54−12742号公報
特許文献5: 特開昭54−17733号公報
特許文献6: 特開昭54−21728号公報
特許文献7: 特開昭53−133445号公報
特許文献8: 特開昭54−17734号公報
特許文献9: 特開昭54−2129号公報
特許文献10: 特開昭53−138229号公報
特許文献11: 特開昭57−195767号公報
特許文献12: 特開昭57−195768号公報
特許文献13: 特開昭57−202545号公報
特許文献14: 特開昭59−129857号公報
特許文献15: 特開昭62−267363号公報
特許文献16: 特開昭64−79753号公報
特許文献17: 特公平3−34503号公報
特許文献18: 特公平4−52459号公報
なお、実施例4〜16,19〜21及び23、並びに、感光体実施例1〜13及び16〜18は、それぞれ、参考例4〜16,19〜21及び23、並びに、感光体参考例1〜13及び16〜18と読替えるものとする。
フェニル−p−トリルアミン11.5g(0.063mol)、4,4”−ジヨード−p−ターフェニル14.5g(0.030mol)、無水炭酸カリウム5.0g(0.036mol)、銅粉0.38g(0.006mol)、n−ドデカン15mlを混合し、窒素ガスを導入しながら200〜210℃まで加熱し、30時間撹拌した。反応終了後、トルエン400mlで反応生成物を抽出し、不溶分をろ別除去後、ろ液を濃縮乾固した。得られた固形物をカラムクロマトグラフィー(担体;シリカゲル、溶離液;トルエン:ヘキサン=1:4)によって精製し、N,N’−ジフェニル−N,N’−ジ−p−トリル−4,4”−ジアミノ−p−ターフェニル(化合物(1))を13.6g(収率;76.4%、融点;167.2〜168.2℃)得た。
(4−メトキシ−2−メチルフェニル)フェニルアミン14.1g(0.066mol)、4,4”−ジヨード−p−ターフェニル14.5g(0.030mol)、無水炭酸カリウム5.0g(0.036mol)、銅粉0.38g(0.006mol)、n−ドデカン15mlを混合し、窒素ガスを導入しながら200〜210℃まで加熱し、30時間撹拌した。反応終了後、トルエン400mlで反応生成物を抽出し、不溶分をろ別除去後、ろ液を濃縮乾固した。得られた固形物をカラムクロマトグラフィー(担体;シリカゲル、溶離液;トルエン:ヘキサン=1:2)によって精製し、N,N’−ジ(4−メトキシ−2−メチルフェニル)−N,N’−ジフェニル−4,4”−ジアミノ−p−ターフェニル(化合物(2))を15.7g(収率;80.0%、融点;180.8〜183.4℃)得た。
5−アミノインダン(東京化成工業製)33.3g(0.25mol)を氷酢酸250mlに溶解した後、50℃に加熱し、無水酢酸51.0g(0.5mol)を滴下した。滴下終了後、4時間撹拌した。反応終了後、反応液を氷水1500ml中に撹拌しながら注加した。析出した結晶をろ別し、水1000mlで洗浄した。得られた結晶を乾燥して5−(N−アセチルアミノ)インダンを37.06g(収率;84.6%、融点;100.5〜103.5℃)得た。
アルコール可溶性ポリアミド(アミランCM−4000、東レ製)1部をメタノール13部に溶解した。これに酸化チタン(タイペークCR−EL、石原産業製)5部を加え、ペイントシェーカーで8時間分散し、アンダーコート層用塗布液を作製した後、アルミ蒸着PETフィルムのアルミ面上にワイヤーバーを用いて塗布乾燥し、厚さ1μmのアンダーコート層を形成した。
1.5部をポリビニルブチラール樹脂(エスレックBL−S、積水化学工業(株)製)の3%シクロヘキサノン溶液50部に加え、超音波分散機で1時間分散した。得られた分散液を前記したアンダーコート層上にワイヤーバーを用いて塗布後、常圧下110℃で1時間乾燥して膜厚0.6μmの電荷発生層を形成した。
の13.0%テトラヒドロフラン溶液962部に加え超音波をかけてp−ターフェニル化合物を完全に溶解させた。この溶液を前記した電荷発生層上にワイヤーバーで塗布し、常圧下110℃で30分間乾燥して膜厚20μmの電荷輸送層を形成し感光体を作製した。
実施例4においてポリカーボネート樹脂No.1を用いる代わりに下記ポリカーボネート樹脂(ポリカーボネート樹脂No.2)を用いる以外は実施例4と同様にして感光体を作製した。
実施例4において電荷発生剤No.1を用いる代わりに、Cu−KαのX線回折スペクトルにおける回折角2θ±0.2°が7.5、10.3、12.6、22.5、24.3、25.4、28.6に強いピークを有するチタニルフタロシアニン(電荷発生剤No.2)を、電荷輸送剤No.3を用いる代わりに化合物(2)のp−ターフェニル化合物(電荷輸送剤No.2)を用いる以外は実施例4と同様にして感光体を作製した。
実施例6においてポリカーボネート樹脂No.1を用いる代わりにポリカーボネート樹脂No.2を用いる以外は実施例6と同様にして感光体を作製した。
実施例4において電荷発生剤No.1を用いる代わりに、Cu−KαのX線回折スペクトルにおける回折角2θ±0.2°が9.3、10.6、13.2、15.1、20.8、23.3、26.3に強いピークを有するチタニルフタロシアニン(電荷発生剤No.3)を、電荷輸送剤No.2を用いる代わりに化合物(1)のp−ターフェニル化合物(電荷輸送剤No.1)を用いる以外は実施例4と同様にして感光体を作製した。
実施例8においてポリカーボネート樹脂No.1を用いる代わりにポリカーボネート樹脂No.2を用いる以外は実施例8と同様にして感光体を作製した。
アルコール可溶性ポリアミド(アミランCM−8000、東レ製)10部をメタノール190部に溶解後、アルミ蒸着PETフィルムのアルミ面上にワイヤーバーを用いて塗布乾燥し、厚さ1μmのアンダーコート層を形成した。
1.5部をポリビニルブチラール樹脂(エスレックBL−S、積水化学工業(株)製)の3%シクロヘキサノン溶液50部に加え、超音波分散機で1時間分散した。得られた分散液を前記したアンダーコート層上にワイヤーバーを用いて塗布後、常圧下110℃で1時間乾燥して膜厚0.6μmの電荷発生層を形成した。
実施例10においてポリカーボネート樹脂No.1を用いる代わりにポリカーボネート樹脂No.2を用いる以外は実施例10と同様にして感光体を作製した。
実施例6において電荷輸送剤No.2を用いる代わりに電荷輸送剤No.1を用いる以外は実施例6と同様にして感光体を作製した。
実施例12においてポリカーボネート樹脂No.1を用いる代わりにポリカーボネート樹脂No.2と下記ポリカーボネート樹脂(ポリカーボネート樹脂No.3)の8:2質量比の混合物を用いる以外は実施例12と同様にして感光体を作製した。
実施例4においてポリカーボネート樹脂No.1を用いる代わりに下記ポリカーボネート樹脂(ポリカーボネート樹脂No.4)を用いる以外は実施例4と同様にして感光体を作製した。
実施例4においてポリカーボネート樹脂No.1を用いる代わりに下記ポリカーボネート樹脂(ポリカーボネート樹脂No.5)を用いる以外は実施例4と同様にして感光体を作製した。
実施例4においてポリカーボネート樹脂No.1を用いる代わりに下記ポリカーボネート樹脂(ポリカーボネート樹脂No.6)を用いる以外は実施例4と同様にして感光体を作製した。
実施例6において電荷輸送剤No.2を用いる代わりに電荷輸送剤No.3と化合物(4)のp−ターフェニル化合物(電荷輸送剤No.4)の9:1質量比の混合物を用いる以外は実施例6と同様にして感光体を作製した。
実施例17においてポリカーボネート樹脂No.1を用いる代わりにポリカーボネート樹脂No.2を用いる以外は実施例17と同様にして感光体を作製した。
電荷発生剤として下記ビスアゾ顔料(電荷発生剤No.5)
1.0部及びポリビニルブチラール樹脂(エスレックBL−S、積水化学工業(株)製)の5%シクロヘキサノン溶液8.6部をシクロヘキサノン83部に加え、ボールミルにて粉砕分散処理を48時間行った。得られた分散液を導電性支持体であるアルミ蒸着PETフィルムのアルミ面上にワイヤーバーを用いて塗布乾燥し、厚さ0.8μmの電荷発生層を形成した。
一方、電荷輸送剤として電荷輸送剤No.1、100部をポリカーボネート樹脂No.5の13.0%テトラヒドロフラン溶液962部に加え超音波をかけてp−ターフェニル化合物を完全に溶解させた。この溶液を前記した電荷発生層上にワイヤーバーで塗布し、常圧下110℃で30分間乾燥して膜厚20μmの電荷輸送層を形成し感光体を作製した。
実施例19において電荷発生剤No.5を用いる代わりに下記ビスアゾ顔料(電荷発生剤No.6)を用いる以外は実施例19と同様にして感光体を作製した。
電荷発生剤として下記ビスアゾ顔料(電荷発生剤No.7)
1.0部及びポリエステル樹脂(バイロン200、東洋紡(株)製)の5%テトラヒドロフラン溶液8.6部をテトラヒドロフラン83部に加え、ボールミルにて粉砕分散処理を48時間行った。得られた分散液を導電性支持体であるアルミ蒸着PETフィルムのアルミ面上にワイヤーバーを用いて塗布乾燥し、厚さ0.8μmの電荷発生層を形成した。
一方、電荷輸送剤として電荷輸送剤No.3、100部をポリカーボネート樹脂No.2の13.0%テトラヒドロフラン溶液962部に加え超音波をかけてp−ターフェニル化合物を完全に溶解させた。この溶液を前記した電荷発生層上にワイヤーバーで塗布し、常圧下110℃で30分間乾燥して膜厚20μmの電荷輸送層を形成し感光体を作製した。
1: 導電性支持体
2: 電荷発生層
3: 電荷輸送層
4: 感光層
5: アンダーコート層
6: 電荷輸送物質含有層
7: 電荷発生物質
8: 保護層
Claims (3)
- 導電性支持体上に下記式(1)〜(5)から選択されるp−ターフェニル化合物の2種以上と、
一般式(I)
(式中、R1及びR2は同一でも異なってもよく水素原子、置換もしくは無置換のアルキル基または置換もしくは無置換のアリール基を表し、R1とR2が共同で環を形成しても良く、R3、R4、R5、R6、R7、R8、R9及びR10は同一でも異なってもよく水素原子、置換もしくは無置換のアルキル基、置換もしくは無置換のアリール基またはハロゲン原子を表し、pとqはモル組成分率を表し(qは0も含む)、pとqの比は式0≦q/p≦2を満足する関係にあり、Zは置換もしくは無置換の炭素数が1〜5のアルキレン基、置換もしくは無置換の4,4’−ビフェニレン基または一般式(II)
(式中、R11及びR12は同一でも異なってもよく水素原子、置換もしくは無置換のアルキル基または置換もしくは無置換のアリール基を表し、R11とR12が共同で環を形成しても良く、R13、R14、R15及びR16は同一でも異なってもよく水素原子、置換もしくは無置換のアルキル基、置換もしくは無置換のアリール基またはハロゲン原子を表し、rは0から3の整数を表す。)で表される2価基を表す。)で表されるポリカーボネート樹脂の1種以上を、p−ターフェニル化合物とポリカーボネート樹脂の質量比2:8ないし7:3の範囲内で含有する層を有する電子写真用感光体、ただし、ポリカーボネート樹脂を1種のみ用いる場合においては、一般式(I)で表されるポリカーボネート樹脂の構造がR1及びR2がメチル基で、R3、R4、R5、R6、R7、R8、R9及びR10が水素原子で、qが0である場合を除く。 - 一般式(I)で表されるポリカーボネート樹脂が、下記構造式(6)〜(28)のいずれかで表されるポリカーボネート樹脂の少なくとも1種からなる、請求項1記載の電子写真用感光体、ただし、構造式(6)で表されるポリカーボネート樹脂のみからなる場合を除く。
- 式(1)〜(5)から選択されるp−ターフェニル化合物の2種以上と、一般式(I)で表されるポリカーボネート樹脂の1種以上を、p−ターフェニル化合物とポリカーボネート樹脂の質量比3:7ないし6:4の範囲内で含有する、請求項1または請求項2記載の電子写真用感光体。
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-
2005
- 2005-11-21 JP JP2006545220A patent/JP4809777B2/ja active Active
- 2005-11-21 CN CNA2005800397212A patent/CN101061437A/zh active Pending
- 2005-11-21 KR KR1020127032255A patent/KR101321646B1/ko active IP Right Grant
- 2005-11-21 EP EP05809273.5A patent/EP1816522B1/en active Active
- 2005-11-21 US US11/719,863 patent/US7790342B2/en active Active
- 2005-11-21 CN CN2011103462738A patent/CN102608881A/zh active Pending
- 2005-11-21 KR KR1020077011602A patent/KR101245402B1/ko active IP Right Grant
- 2005-11-21 EP EP12158567A patent/EP2485092A1/en not_active Withdrawn
- 2005-11-21 WO PCT/JP2005/021750 patent/WO2006054805A1/ja active Application Filing
- 2005-11-22 TW TW101113728A patent/TW201235802A/zh unknown
- 2005-11-22 TW TW094140921A patent/TWI385196B/zh active
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2010
- 2010-07-21 US US12/840,679 patent/US20100291480A1/en not_active Abandoned
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- 2011-05-31 JP JP2011122246A patent/JP4880079B2/ja active Active
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Also Published As
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EP1816522A4 (en) | 2009-11-04 |
US20100291480A1 (en) | 2010-11-18 |
US20130266343A1 (en) | 2013-10-10 |
KR20130008637A (ko) | 2013-01-22 |
US8808951B2 (en) | 2014-08-19 |
EP1816522B1 (en) | 2013-12-25 |
TW201235802A (en) | 2012-09-01 |
EP2485092A1 (en) | 2012-08-08 |
US7790342B2 (en) | 2010-09-07 |
JP2011164659A (ja) | 2011-08-25 |
CN102608881A (zh) | 2012-07-25 |
JP4809777B2 (ja) | 2011-11-09 |
US20090226830A1 (en) | 2009-09-10 |
TWI385196B (zh) | 2013-02-11 |
CN101061437A (zh) | 2007-10-24 |
WO2006054805A1 (ja) | 2006-05-26 |
KR20070093968A (ko) | 2007-09-19 |
JPWO2006054805A1 (ja) | 2008-06-05 |
TW200628512A (en) | 2006-08-16 |
KR101245402B1 (ko) | 2013-03-19 |
KR101321646B1 (ko) | 2013-10-23 |
EP1816522A1 (en) | 2007-08-08 |
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