JPH0435756B2 - - Google Patents
Info
- Publication number
- JPH0435756B2 JPH0435756B2 JP4465387A JP4465387A JPH0435756B2 JP H0435756 B2 JPH0435756 B2 JP H0435756B2 JP 4465387 A JP4465387 A JP 4465387A JP 4465387 A JP4465387 A JP 4465387A JP H0435756 B2 JPH0435756 B2 JP H0435756B2
- Authority
- JP
- Japan
- Prior art keywords
- general formula
- resin
- group
- electrophotographic photoreceptor
- charge transfer
- 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.)
- Expired
Links
- 108091008695 photoreceptors Proteins 0.000 claims description 31
- 150000001875 compounds Chemical class 0.000 claims description 30
- 238000012546 transfer Methods 0.000 claims description 22
- 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 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 229920005989 resin Polymers 0.000 description 27
- 239000011347 resin Substances 0.000 description 27
- 230000035945 sensitivity Effects 0.000 description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 238000000576 coating method Methods 0.000 description 8
- -1 methoxyphenyl group Chemical group 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 230000006866 deterioration Effects 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 4
- 229920000139 polyethylene terephthalate Polymers 0.000 description 4
- 239000005020 polyethylene terephthalate Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000004677 Nylon Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 230000007613 environmental effect Effects 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229920001778 nylon Polymers 0.000 description 3
- 229920005668 polycarbonate resin Polymers 0.000 description 3
- 239000004431 polycarbonate resin Substances 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 229920002292 Nylon 6 Polymers 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000004419 Panlite Substances 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 239000005018 casein Substances 0.000 description 2
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 2
- 235000021240 caseins Nutrition 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000000586 desensitisation Methods 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000005011 phenolic resin Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 2
- 229920002401 polyacrylamide Polymers 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920001230 polyarylate Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 229920000915 polyvinyl chloride Polymers 0.000 description 2
- 239000004800 polyvinyl chloride Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 229920002050 silicone resin Polymers 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000000758 substrate Substances 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- WUPHOULIZUERAE-UHFFFAOYSA-N 3-(oxolan-2-yl)propanoic acid Chemical compound OC(=O)CCC1CCCO1 WUPHOULIZUERAE-UHFFFAOYSA-N 0.000 description 1
- 229920002799 BoPET Polymers 0.000 description 1
- 229910001369 Brass Inorganic materials 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- 229920000571 Nylon 11 Polymers 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 229910001370 Se alloy Inorganic materials 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- HMDDXIMCDZRSNE-UHFFFAOYSA-N [C].[Si] Chemical compound [C].[Si] HMDDXIMCDZRSNE-UHFFFAOYSA-N 0.000 description 1
- UMVBXBACMIOFDO-UHFFFAOYSA-N [N].[Si] Chemical compound [N].[Si] UMVBXBACMIOFDO-UHFFFAOYSA-N 0.000 description 1
- 239000011358 absorbing material Substances 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000010951 brass Substances 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 229910052980 cadmium sulfide Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000012461 cellulose resin Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 229920006242 ethylene acrylic acid copolymer Polymers 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 229910052809 inorganic oxide Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000000113 methacrylic resin Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 229920006287 phenoxy resin Polymers 0.000 description 1
- 239000013034 phenoxy resin Substances 0.000 description 1
- 229920002382 photo conductive polymer Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001470 polyketone Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 229920002717 polyvinylpyridine Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- CMMXCVYESRODNH-UHFFFAOYSA-N trichloroepoxyethane Chemical class ClC1OC1(Cl)Cl CMMXCVYESRODNH-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
- G03G5/0664—Dyes
- G03G5/0666—Dyes containing a methine or polymethine group
- G03G5/0668—Dyes containing a methine or polymethine group containing only one methine or polymethine group
Description
〔発明の目的〕
（産業上の利用分野）
本発明は、電子写真感光体に関し、更に詳細に
言えば、優れた露光感光特性、波長特性を有する
電子写真感光体に関する。
（従来の技術）
従来、電子写真感光体の感光体としては、セレ
ン、セレン合金、酸化亜鉛、硫化カドミウムおよ
びテルルなどの無機光導電体を用いたものが主と
して使用されて来た。近年、半導体レーザーの発
展は目覚ましく、小型で安定したレーザー発振器
が安価に入手出来るようになり、電子写真用光源
として用いられ始めている。しかし、これらの装
置に短波長光を発振する半導体レーザーを用いる
のは、寿命、出力等を考えれば問題が多い。従つ
て、従来用いられて来た短波長領域に感度を持つ
材料を半導体レーザー用に使うには不適当であ
り、長波長領域（780nm以上）に高感度を持つ材
料を研究する必要が生じて来た。最近は有機系の
材料、特に長波長領域に感度を持つことが期待さ
れるフタロシアニンを使用し、これを積層した積
層型有機感光体の研究が盛んに行なわれている。
長波長領域に高感度を持つフタロシアニン（Pc）
系材料としては、既に、ε型銅フタロシアニン
（ε−CuPc）、Ｘ型無金属フタロシアニン（Ｘ−
H2Pc）およびτ型無金属フタロシアニンが公知
であるが、従来の電荷移動剤と組み合わせて形成
された電子写真感光体は、感度、繰り返し使用時
の安定性およびフオトメモリー性等に問題があ
り、実際に使用する場合十分なものとは言い難い
レベルであつた。
（発明が解決しようとする問題点）
本発明の目的は、優れた露光感度特性、780nm
以上の長波長領域に高感度、繰り返し使用時に安
定で、フオトメモリー性の良好である電子写真感
光体を得ることにある。
〔発明の構成〕
（問題点を解決するための手段および作用）
上記の目的は、導電性支持体に、電荷発生層お
よび電荷移動層を積層してなる電子写真感光体に
おいて、電荷発生層が、τ、τ′，ηおよびη′型無
金属フタロシアニンから選ばれる少なくとも一種
の無金属フタロシアニンを含有し、電荷移動層が
下記一般式〔〕で示される化合物を含有するこ
と、または一般式〔〕および一般式〔〕で示
される化合物を共に含有する電荷移動層を積層し
てなる電子写真感光体により達成される。
一般式〔〕
（式中、R1，R2は、水素原子、アルキル基、
アルコキシ基またはアリール基、R3、R4．R5は
水素原子または−NR1（R2）基を示し、ｎは０ま
たは１である。）
一般式〔〕
（式中、R6は炭素数アルキル基、アリール基
を示し、R1およびR2は、上記と同じ意味を示
す。）
本発明で使用されるτ，τ′，ηおよびη′型無金
属フタロシアニンは特開昭57−66963号、同58−
183757号公報に開示された方法で製造されたもの
である。
本発明で使用される一般式〔〕もしくは
〔〕の置換基R1〜R5におけるアルキル基として
は、メチル基、エチル基、プロピル基等の低級ア
ルキル基、あるいはベンジル基等の置換アルキル
基であり、アルコキシ基としては、メトキシ基、
エトキシ基、ブトキシ基等があり、アリール基と
しては、フエニル基、ナフチル基等の他、トリル
基、メトキシフエニル基等の置換アリール基があ
る。
本発明において一般式〔〕の特に好ましい例
としては、R1，R2がともにエチル基であり、R3
〜R4が水素原子である化合物、あるいはR1，R2
がともにエチル基であり、R3〜R4のいずれか−
NC2H5（C2H5）基である化合物である。また、
一般式〔〕の特に好ましい例としては、R6が
フエニル基、R1がフエニル基、R2がフエニル基
もしくはエチル基である化合物である。
本発明の電子写真感光体は、導電性基板上に、
下引き層、電荷発生層、電荷移動層の順に積層さ
れたものが望ましいが、下引き層、電荷移動層、
電荷発生層の順で積層されたものでも良い。
また、必要に応じて、樹脂また無機酸化物で最
上層にオーバーコータ層を設けることも出来る。
電荷発生層の塗工は、樹脂なしで、あるいは必
要があれば適当な樹脂溶液中にτ，τ′，ηおよび
η型のうち一種、または二種以上を分散塗工した
後に、乾燥して設ける。
塗工は、スピンコーター、アプリケーター、ス
プレーコータ、バーコーター、浸漬コーター、ド
クターブレード、ローラーコーター、カーテンコ
ータ、ビードコーター装置を用いて行ない、乾燥
は、望ましくは加熱乾燥で40〜200℃で、10分〜
６時間の範囲で静止または送風条件下で行なう。
乾燥後膜厚は０。01から５ミクロン、望ましくは
0.1から１ミクロンになるように塗工される。
電荷発生層を塗工によつて形成する際に用いう
るバインダーとしては広範な絶縁性樹脂ら選択で
き、またポリ−Ｎ−ビニルカルバゾール、ポリビ
ニルアントラセンやポリビニルピレンなどの有機
光導電性ポリマーから選択できる。好ましくは、
ポリビニルブチラール、ポリアリレート（ビスフ
エノールＡとフタル酸の縮重合体など）、ポリカ
ーボネート、ポリエステル、フエノキシ樹脂、ポ
リ酢酸ビニル、アクリル樹脂、ポリアクリルアミ
ド樹脂、ポリアミド樹脂、ポリビニルピリジン、
セルロース系樹脂、ウレタン樹脂、エポキシ樹
脂、シリコン樹脂、ポリスチレン、ポリケトン樹
脂、ポリ塩化ビニル、塩ビー酸ビ共重合体、ポリ
ビニルアセタール、ポリアクリロニトリル、フエ
ノール樹脂、メラミン樹脂、カゼイン、ポリビニ
ルアルコール、ポリビニルピロリドン等の絶縁性
樹脂を挙げることができる。電荷発生層中に含有
する樹脂は、100重量％以下、好ましくは40重量
％以下が適している。またこれらの樹脂は、１種
または２種以上組合せて用いても良い。これらの
樹脂を溶解する溶剤は樹脂の種類によつて異な
り、後述する電荷移動層や下引き層を塗工時に影
響を与えないものから選択することが好ましい。
具体的にはベンゼン、キシレン、リグロイン、モ
ノクロルベンゼン、ジクロルベンゼンなどの芳香
族炭化水素、アセトン、メチルエチルケトン、シ
クロヘキサノンなどのケトン類、メタノール、エ
タノール、イソプロパノールなどのアルコール
類、酢酸エチル、メチルセロソルブ、などのエス
テル類、四塩化炭素、クロロホルム、ジクロルメ
タン、ジクロルエタン、トリクロルエチレンなど
の脂肪族ハロゲン化炭化水素類、テトラヒドロフ
ラン、ジオキサン、エチレングリコールモノメチ
ルエーテルなどのエーテル類、Ｎ，N′−ジメチ
ルホルムアミド、Ｎ，Ｎ−ジメチルアセトアミド
などのアミド類、およびジメチルスルホキシドな
どのスルホキシド類が用いられる。
電荷移動層は、電荷移動剤単体または結着剤樹
脂に適当な溶剤に溶解分散させて形成される。電
荷移動剤は、一般式〔〕および〔〕で示され
る化合物を使用する。
電荷移動層に用いられる樹脂は、シリコン樹
脂、ケトン樹脂、ポリメチルメタクリレート、ポ
リ塩化ビニル、アクリル樹脂、ポリアリレート、
ポリエステル、ポリカーボネート、ポリスチレ
ン、アクリロニトリル−シチレンコポリマー、ア
クリロニトリル−ブタジエンコポリマー、ポリビ
ニルプチラール、ポリビニルホルマール、ポリス
ルホン、ポリアクリルアミド、ポリアミド、塩素
化ゴムなどの絶縁性樹脂、ポリ−Ｎ−ビニルカル
バゾール、ポリビニルアントラセン、ポリビニル
ピレンなどが用いられる。
塗工方法は、スピンコーター、アプリケータ
ー、スプレーコーター、バーコーター、浸漬コー
ター、ドクターブレード、ローラーコーター、カ
ーテンコーター、ビードコーター装置を用いて行
ない、乾燥後膜厚は５から50ミクロン、望ましく
は10から20ミクロンになるように塗工されるもの
が良い。
樹脂と一般式〔〕の化合物との配合割合は、
樹脂１重量部当たり、一般式〔〕の化合物を
0.1〜10重量部とすることが好ましい。
また、一般式〔〕および〔〕で示される化
合物を共に使用する場合、一般式〔〕および
〔〕の化合物の配合割合は、いずれでも効果を
認めることが出来るが、一般式〔〕の化合物１
重量部当たり、一般式〔〕の化合物0.1〜10重
量部が望ましい。樹脂に対して一般式〔〕およ
び〔〕の化合物の混合物の配合割合、樹脂１重
量部当たり、混合物を0.1〜10重量部とすること
が好ましい。また、これらの樹脂は、１種または
２種以上組み合わせて用いても良い。
一般式〔〕の化合物を電荷移動剤として使用
した感光体は、高感度でありフオトメモリー性も
少なく、光による劣化が少ないという利点があ
る。また、高感度のため電荷移動層中の電荷移動
剤の量を減らすことも可能であり、感光体の耐久
性および耐環境性に多大な効果を及ぼす。それに
加えて、一般式〔〕の化合物に一般式〔〕の
化合物を混合して、電荷移動層を形成すると以上
の効果に加えて、帯電性が向上し、低温時での特
性の劣化を防止するなど、バランスのとれた感光
体となる。
また、本発明の電荷移動層を形成させる際に使
用する溶剤は多数の有用な有機溶剤を包含してい
る。例えば、ベンゼン、トルエン、キシレン、ク
ロルベンゼン、ナフタリンなどの芳香族炭化水素
類。アセトン、２−ブタノンなどのケトン類。塩
化メチレン、塩化エチレン、クロロホルムなどの
ハロゲン化脂肪族炭化水素類。テトラヒドロフラ
ン、１，４−ジオキサン、エチルエーテルなどの
環状、もしくは直鎖状のエーテル類など、あるい
はこれらの混合溶剤を挙げることが出来る。
これらの各層に加えて、帯電性の低下防止、接
着性向上などの目的で下引き層を導電性基板上に
設けることができる。下引き層として、ポリエチ
レン、ポリプロピレン、アルリル樹脂、メタクリ
ル樹脂、塩化ビニル樹脂、酢酸ビニル樹脂、フエ
ノール樹脂、エポキシ樹脂、ピリエステル樹脂、
アルキド樹脂、ポリカーボネート樹脂、ポリウレ
タン、塩酢ビ樹脂、塩化ビニリデン樹脂、ナイロ
ン６、ナイロン６６、ナイロン１１、ナイロン６
１０、共重合ナイロン、アルコキシメチル化ナイ
ロンなどのアルコール可溶性ボリアミド、カゼイ
ン、ポリビニルアルコール、ニトロセルロース、
エチレン−アクリル酸コポリマー、ゼラチン、ポ
リウレタン、ポリビニルブチラールおよび酸化ア
ルミニウムなどの金属酸化物が用いられる。ま
た、塩化亜鉛、塩化チタン等の金属酸化物、窒素
ケイ素、炭素ケイ素やカーボンブラツクなどの導
電性および誘電性粒子を樹脂中に含有させて下引
き層の導電性を調製することも出来る。
膜厚は0.1から50ミクロン、望ましくは0.1から
１ミクロンに塗工されるものが良い。
本発明の電子写真感光体に用いる支持体として
は、導電性が付与されていれば、何れのものでも
良く、従来使われている何れのタイプの導電層で
あつてもさしつかえない。具体的には、アルミニ
ウム、銅、ステンレス、鉄、真ちゆう、スズおよ
びニツケルなどの金属や、それら金属を用いて
紙、プラスチツク、ポリエチレンテレフタレート
（PET）などの高分子フイルム上に蒸着またはラ
ミネート等の処理を行い、導電性を持たせたもの
であつても良い。また、その型状についてはシー
ト状あるいはシリンダー状、その他のものであつ
ても差支えない。
プリンター用のデジタル光源として、LEDも
実用化されている。
可視光領域のLEDも使われているが、一般に
実用化されているものは、650nm以上、標準的に
は660nmの発振波長を持つている。当該電子写真
感光体は、650nm前後にも分光感度ピークを持つ
ため、LED用材料としても有効である。
本発明の材料は800nm以上に分光感度ピークが
あり、電子写真感光体として複写機、プリンター
に使用されるだけでなく、太陽電池、光電変換阻
止および光デイスク用吸収材料としても好適であ
る。
以下、本発明の実施例について具体的に説明す
る。例中で部とは重量部を示す。
実施例 １
共重合ナイロン（東レ製アミランCM−8000）
10部をエタノール190部とともにボールミルで３
時間混合し、溶解させた塗液を、ポリエチレンテ
レフタレート（PET）フイルム上にアルミニウ
ムを蒸着したシート上に、ワイヤーバーで塗布し
た後、100℃で１時間乾燥させて膜厚0.5ミクロン
の下引き層を持つシートを得た。
次に、τ型無金属フタロシアニン１部とブチラ
ール樹脂（エスレツクBH−３：積水化学(株)製）
１部およびTHF30部をボールミルで４時間分散
した。この部散液を先に形成した下引き層の上に
塗布し、100℃で２時間乾燥させた後、0.3ミクロ
ンの電荷発生層を得た。
さらに、下記化合物(a)を１部、ポリカーボネー
ト樹脂（パンライトＬ−1250：帝人化成(株)製）１
部を塩化メチレン８部中で混合溶解した。この液
を電荷発生層上に塗布し、80℃で１時間乾燥させ
た後、15ミクロンの電荷移動層を形成し、電子写
真感光体を得た。
本実施例で得られた電子写真感光体を、静電複
写紙試験装置SP−428（川口電機製）によりスタ
テイツクモード２、コロナ帯電は−5.2KVで、表
面電位および5Luxの白色光を照射して帯電量が
１／２および1/5で減少する時間から白色光半減露光
量感度（Ｅ1/2およびＥ1/5）を調べた。また、繰
り返し特性の評価は−5.2KV、コロナ線測度
20m／minの条件で帯電（V0）、２秒間暗所に放
置（V2）、5Luxで３秒露光の順で繰り返し、表
面電位、残留電位、感度の劣化を測定した。なお
残留電位は光照射３秒後の電位（VR3）である。
フオトメモリー性（PM）は、本感光体を600
ルツクス下で３分間放置した後、暗所に１分間放
置し、再び同一条件で静電特性を測定する。そこ
で、600ルツクス照射前の感光体の帯電電位と600
ルツクス照射後の感光体の帯電電位（V0）の変
化をフオトメモリー（PM）とした。従つて、フ
オトメモリー（PM）は次式で示される。
PM＝強照度（600ルツクス）露光前の表面電
位−強照度露光後の表面電位
[Object of the Invention] (Industrial Application Field) The present invention relates to an electrophotographic photoreceptor, and more specifically, to an electrophotographic photoreceptor having excellent exposure sensitivity characteristics and wavelength characteristics. (Prior Art) In the past, inorganic photoconductors such as selenium, selenium alloys, zinc oxide, cadmium sulfide, and tellurium have been mainly used as photoconductors for electrophotographic photoconductors. In recent years, the development of semiconductor lasers has been remarkable, and small and stable laser oscillators have become available at low cost and are beginning to be used as light sources for electrophotography. However, using semiconductor lasers that emit short wavelength light in these devices has many problems in terms of lifespan, output, etc. Therefore, the conventionally used materials with sensitivity in the short wavelength region are unsuitable for use in semiconductor lasers, and there is a need to research materials with high sensitivity in the long wavelength region (780 nm or more). It's here. Recently, research has been actively conducted on multilayer organic photoreceptors using organic materials, especially phthalocyanine, which is expected to have sensitivity in the long wavelength region.
Phthalocyanine (Pc) with high sensitivity in the long wavelength region
Already, ε-type copper phthalocyanine (ε-CuPc) and X-type metal-free phthalocyanine (X-
H 2 Pc) and τ-type metal-free phthalocyanine are known, but electrophotographic photoreceptors formed in combination with conventional charge transfer agents have problems with sensitivity, stability during repeated use, photomemory properties, etc. However, it was at a level that could hardly be said to be sufficient for actual use. (Problems to be Solved by the Invention) The purpose of the present invention is to provide excellent exposure sensitivity characteristics at 780nm.
The object of the present invention is to obtain an electrophotographic photoreceptor that has high sensitivity in the above long wavelength region, is stable during repeated use, and has good photomemory properties. [Structure of the Invention] (Means and Effects for Solving the Problems) The above object is to provide an electrophotographic photoreceptor in which a charge generation layer and a charge transfer layer are laminated on a conductive support. , τ, τ′, η, and η′ type metal-free phthalocyanine, and the charge transfer layer contains a compound represented by the following general formula [], or the general formula [] This is achieved by an electrophotographic photoreceptor formed by laminating a charge transfer layer containing a compound represented by the general formula []. General formula [] (In the formula, R 1 and R 2 are hydrogen atoms, alkyl groups,
Alkoxy group or aryl group, R 3 , R 4 . R 5 represents a hydrogen atom or a -NR 1 (R 2 ) group, and n is 0 or 1. ) General formula [] (In the formula, R 6 represents a carbon number alkyl group or aryl group, and R 1 and R 2 have the same meanings as above.) τ, τ′, η and η′ type metal-free used in the present invention Phthalocyanine is disclosed in Japanese Patent Application Publication Nos. 57-66963 and 58-
It was manufactured by the method disclosed in Publication No. 183757. The alkyl group in the substituents R 1 to R 5 of the general formula [] or [] used in the present invention is a lower alkyl group such as a methyl group, an ethyl group, a propyl group, or a substituted alkyl group such as a benzyl group. Yes, alkoxy groups include methoxy group,
Examples of the aryl group include an ethoxy group and a butoxy group, and examples of the aryl group include a phenyl group, a naphthyl group, and substituted aryl groups such as a tolyl group and a methoxyphenyl group. In the present invention, as a particularly preferable example of the general formula [], R 1 and R 2 are both ethyl groups, and R 3
~ Compounds where R 4 is a hydrogen atom, or R 1 , R 2
are both ethyl groups, and any one of R 3 to R 4 -
It is a compound that is an NC 2 H 5 (C 2 H 5 ) group. Also,
A particularly preferred example of the general formula [] is a compound in which R 6 is a phenyl group, R 1 is a phenyl group, and R 2 is a phenyl group or an ethyl group. The electrophotographic photoreceptor of the present invention includes, on a conductive substrate,
It is preferable that the undercoat layer, the charge generation layer, and the charge transfer layer are laminated in this order.
The charge generation layer may be laminated in this order. Further, if necessary, an overcoat layer made of resin or inorganic oxide can be provided as the uppermost layer. The charge generation layer can be applied without a resin, or if necessary, one or more types of τ, τ', η, and η types can be dispersed and coated in an appropriate resin solution, and then dried. establish. Coating is performed using a spin coater, applicator, spray coater, bar coater, dip coater, doctor blade, roller coater, curtain coater, or bead coater, and drying is preferably done by heating at 40 to 200°C for 10 minutes. Minutes~
Testing is carried out under stationary or ventilated conditions for a period of 6 hours.
Film thickness after drying is 0.01 to 5 microns, preferably
It is coated to a thickness of 0.1 to 1 micron. The binder that can be used to form the charge generating layer by coating can be selected from a wide variety of insulating resins, and can also be selected from organic photoconductive polymers such as poly-N-vinylcarbazole, polyvinylanthracene, and polyvinylpyrene. . Preferably,
Polyvinyl butyral, polyarylate (condensation polymer of bisphenol A and phthalic acid, etc.), polycarbonate, polyester, phenoxy resin, polyvinyl acetate, acrylic resin, polyacrylamide resin, polyamide resin, polyvinylpyridine,
Cellulose resin, urethane resin, epoxy resin, silicone resin, polystyrene, polyketone resin, polyvinyl chloride, vinyl chloride acid copolymer, polyvinyl acetal, polyacrylonitrile, phenolic resin, melamine resin, casein, polyvinyl alcohol, polyvinylpyrrolidone, etc. The following insulating resins can be mentioned. The resin contained in the charge generation layer is suitably 100% by weight or less, preferably 40% by weight or less. Further, these resins may be used alone or in combination of two or more. The solvent for dissolving these resins varies depending on the type of resin, and it is preferable to select a solvent that does not affect the charge transfer layer and undercoat layer described later during coating.
Specifically, aromatic hydrocarbons such as benzene, xylene, ligroin, monochlorobenzene, dichlorobenzene, ketones such as acetone, methyl ethyl ketone, cyclohexanone, alcohols such as methanol, ethanol, isopropanol, ethyl acetate, methyl cellosolve, etc. esters of carbon tetrachloride, aliphatic halogenated hydrocarbons such as chloroform, dichloromethane, dichloroethane, and trichloroethylene, ethers such as tetrahydrofuran, dioxane, and ethylene glycol monomethyl ether, N,N'-dimethylformamide, N,N -Amides such as dimethylacetamide and sulfoxides such as dimethylsulfoxide are used. The charge transfer layer is formed by dissolving and dispersing a charge transfer agent alone or a binder resin in a suitable solvent. As the charge transfer agent, compounds represented by the general formulas [] and [] are used. Resins used for the charge transfer layer include silicone resin, ketone resin, polymethyl methacrylate, polyvinyl chloride, acrylic resin, polyarylate,
Insulating resins such as polyester, polycarbonate, polystyrene, acrylonitrile-sitylene copolymer, acrylonitrile-butadiene copolymer, polyvinyl butyral, polyvinyl formal, polysulfone, polyacrylamide, polyamide, chlorinated rubber, poly-N-vinyl carbazole, polyvinylanthracene, Polyvinylpyrene and the like are used. The coating method is performed using a spin coater, applicator, spray coater, bar coater, dip coater, doctor blade, roller coater, curtain coater, or bead coater, and the film thickness after drying is from 5 to 50 microns, preferably from 10 to 10. It is best to use a coating that has a thickness of 20 microns. The blending ratio of the resin and the compound of general formula [] is:
Per 1 part by weight of resin, a compound of general formula []
The amount is preferably 0.1 to 10 parts by weight. In addition, when the compounds represented by the general formulas [] and [] are used together, the effect can be recognized regardless of the mixing ratio of the compounds represented by the general formulas [] and [], but the compound of the general formula []
Preferably, 0.1 to 10 parts by weight of the compound of general formula [] is used per part by weight. The mixing ratio of the mixture of the compounds of the general formulas [] and [] to the resin is preferably 0.1 to 10 parts by weight per 1 part by weight of the resin. Further, these resins may be used alone or in combination of two or more. A photoreceptor using a compound of general formula [] as a charge transfer agent has the advantage of high sensitivity, low photomemory property, and little deterioration due to light. Furthermore, due to the high sensitivity, it is possible to reduce the amount of charge transfer agent in the charge transfer layer, which has a great effect on the durability and environmental resistance of the photoreceptor. In addition, by mixing the compound of general formula [] with the compound of general formula [] to form a charge transfer layer, in addition to the above effects, charging properties are improved and properties are prevented from deteriorating at low temperatures. This results in a well-balanced photoreceptor. Additionally, the solvents used in forming the charge transport layer of the present invention include many useful organic solvents. For example, aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene, and naphthalene. Ketones such as acetone and 2-butanone. Halogenated aliphatic hydrocarbons such as methylene chloride, ethylene chloride, and chloroform. Examples include cyclic or linear ethers such as tetrahydrofuran, 1,4-dioxane, and ethyl ether, and mixed solvents thereof. In addition to these layers, an undercoat layer can be provided on the conductive substrate for the purpose of preventing deterioration of chargeability, improving adhesion, and the like. As an undercoat layer, polyethylene, polypropylene, allyl resin, methacrylic resin, vinyl chloride resin, vinyl acetate resin, phenol resin, epoxy resin, pyriester resin,
Alkyd resin, polycarbonate resin, polyurethane, salt vinyl acetate resin, vinylidene chloride resin, nylon 6, nylon 66, nylon 11, nylon 6
10. Alcohol-soluble polyamides such as copolymerized nylon and alkoxymethylated nylon, casein, polyvinyl alcohol, nitrocellulose,
Ethylene-acrylic acid copolymers, gelatin, polyurethane, polyvinyl butyral and metal oxides such as aluminum oxide are used. The conductivity of the undercoat layer can also be adjusted by incorporating conductive and dielectric particles such as metal oxides such as zinc chloride and titanium chloride, silicon nitrogen, silicon carbon, and carbon black into the resin. The coating thickness is preferably 0.1 to 50 microns, preferably 0.1 to 1 micron. The support used in the electrophotographic photoreceptor of the present invention may be any support as long as it is imparted with conductivity, and any type of conductive layer conventionally used may be used. Specifically, metals such as aluminum, copper, stainless steel, iron, brass, tin, and nickel are used, and these metals are used for vapor deposition or lamination on paper, plastic, and polymer films such as polyethylene terephthalate (PET). It may also be made conductive by undergoing the above treatment. Moreover, the shape thereof may be sheet-like, cylindrical, or other shapes. LEDs are also being put into practical use as digital light sources for printers. LEDs in the visible light range are also used, but those in general use have an oscillation wavelength of 650 nm or more, typically 660 nm. Since the electrophotographic photoreceptor has a spectral sensitivity peak around 650 nm, it is also effective as a material for LEDs. The material of the present invention has a spectral sensitivity peak at 800 nm or more, and is suitable not only for use as an electrophotographic photoreceptor in copying machines and printers, but also as an absorbing material for solar cells, photoelectric conversion blocking, and optical disks. Examples of the present invention will be specifically described below. In the examples, parts refer to parts by weight. Example 1 Copolymerized nylon (Amiran CM-8000 manufactured by Toray Industries)
10 parts with 190 parts of ethanol in a ball mill
After mixing and dissolving the coating liquid for a while, the coating liquid was applied with a wire bar onto a sheet of polyethylene terephthalate (PET) film with aluminum vapor-deposited, and then dried at 100°C for 1 hour to form an undercoat layer with a thickness of 0.5 microns. Got a sheet with. Next, 1 part of τ-type metal-free phthalocyanine and butyral resin (Eslec BH-3: manufactured by Sekisui Chemical Co., Ltd.)
1 part and 30 parts of THF were dispersed in a ball mill for 4 hours. This partial dispersion was applied onto the previously formed undercoat layer and dried at 100° C. for 2 hours to obtain a charge generation layer of 0.3 microns. Furthermore, 1 part of the following compound (a), 1 part of polycarbonate resin (Panlite L-1250: manufactured by Teijin Kasei Ltd.)
1 part was mixed and dissolved in 8 parts of methylene chloride. This liquid was applied onto the charge generation layer and dried at 80° C. for 1 hour to form a charge transfer layer of 15 microns to obtain an electrophotographic photoreceptor. The electrophotographic photoreceptor obtained in this example was irradiated with surface potential and white light of 5 Lux in static mode 2 using an electrostatic copying paper tester SP-428 (manufactured by Kawaguchi Denki), with a corona charge of -5.2 KV. The white light half-reduction exposure sensitivity (E1/2 and E1/5) was determined from the time at which the charge amount decreased by 1/2 and 1/5. In addition, the evaluation of repeatability is -5.2KV, corona line measurement
Charging (V 0 ) at 20 m/min, leaving in the dark for 2 seconds (V 2 ), and exposing for 3 seconds at 5 Lux were repeated in this order to measure surface potential, residual potential, and deterioration in sensitivity. Note that the residual potential is the potential (VR 3 ) after 3 seconds of light irradiation. The photomemory property (PM) of this photoreceptor is 600
After leaving it under lux for 3 minutes, it was left in a dark place for 1 minute, and the electrostatic properties were measured again under the same conditions. Therefore, the charged potential of the photoconductor before 600 lux irradiation and 600 lux
The change in the charged potential (V 0 ) of the photoreceptor after irradiation with lux was defined as photo memory (PM). Therefore, photo memory (PM) is expressed by the following equation. PM = Surface potential before strong illuminance (600 lux) exposure - Surface potential after strong illuminance exposure
【表】【table】
【表】
第１表および第２表に示した結果より、本実施
例により得られた電子写真感光体は、感度が優
れ、残留電位も少なく、10000回の繰り返し試験
後も、初期の特性とほとんど変わらない極めて良
好な結果が得られた。また、フオトメモリー
（PM）も小さく、照射光に対して安定な感光体
であることがわかる。
実施例 ２
実施例１と同様の方法で下引き層および電荷発
生層を塗工したPETフイルム上に、化合物(a)を
0.5部、下記化合物(b)を0.5部、ポリカーボネート
樹脂（パンライトＬ−1250：帝人化成(株)製）１部
を塩化メチレン８部中で混合溶解した液を電荷発
生層上に塗布し、80℃で１時間乾燥させた後、15
ミクロンの電荷移動層を作成し、電子写真感光体
を作成した。
[Table] From the results shown in Tables 1 and 2, the electrophotographic photoreceptor obtained in this example has excellent sensitivity, low residual potential, and even after 10,000 repeated tests, it maintains its initial characteristics. Very good results with almost no difference were obtained. Furthermore, the photomemory (PM) is small, indicating that the photoreceptor is stable against irradiation light. Example 2 Compound (a) was applied onto a PET film coated with an undercoat layer and a charge generation layer in the same manner as in Example 1.
0.5 parts of the following compound (b) and 1 part of polycarbonate resin (Panlite L-1250, manufactured by Teijin Kasei Ltd.) were mixed and dissolved in 8 parts of methylene chloride, and a solution was applied on the charge generation layer. After drying at 80℃ for 1 hour, 15
A micron charge transfer layer was created, and an electrophotographic photoreceptor was created.
【表】【table】
【表】
により得られた電子写真感光体も、良好な特性を
示した。
さらに、実施例１および２で得られた電子写真
感光体の特性を環境温度を変えて測定した。結果
を第５表に示す。[Table] The electrophotographic photoreceptor obtained according to the method also showed good characteristics. Further, the characteristics of the electrophotographic photoreceptors obtained in Examples 1 and 2 were measured at different environmental temperatures. The results are shown in Table 5.
【表】
実施例１の化合物(a)で示される化合物を単独で
使用した場合、測定温度10℃では25℃室温に比べ
減感が大きいが、実施例２の化合物(a)および化合
物(b)の混合物を使用した場合、減感が少なくな
り、温度による特性変化が少ないことがわかる。
従つて、化合物(a)を使用した電子写真感光体は、
電子写真諸特性は優れているが、低温時での特性
の劣化があり、化合物(a)に化合物(b)の化合物を加
えて使用することにより、さらに良好な特性が得
られた。また、耐湿性、耐環境性（O3やNOX他
による劣化）も良好であつた。
比較例 １〜２
実施例１で用いた化合物(a)に代えて下記に示す
電荷移動剤を用いた他は、すべて同じ方法で電子
写真感光体を作成した。
上記の電荷移動剤を使用した電子写真感光体の
電子写真特性を第６表および第７表に示す。[Table] When the compound represented by compound (a) of Example 1 is used alone, desensitization is greater at the measurement temperature of 10°C than at 25°C, but when the compound (a) and compound (b) of Example 2 are used alone, It can be seen that when a mixture of ) is used, there is less desensitization and changes in properties due to temperature are small.
Therefore, the electrophotographic photoreceptor using compound (a) is
Although various electrophotographic properties are excellent, the properties deteriorate at low temperatures, and even better properties were obtained by adding compound (b) to compound (a). In addition, moisture resistance and environmental resistance (deterioration due to O 3 , NO x , etc.) were also good. Comparative Examples 1 to 2 Electrophotographic photoreceptors were prepared in the same manner as in Example 1, except that the charge transfer agent shown below was used in place of compound (a). Tables 6 and 7 show the electrophotographic properties of the electrophotographic photoreceptor using the above charge transfer agent.
【表】
実施例１と比較すると残留電位が高く、感度も
劣つている。また、フオトメモリーも大きく、光
照射により表面電位が低下している。[Table] Compared to Example 1, the residual potential is higher and the sensitivity is inferior. In addition, the photomemory is large, and the surface potential is reduced by light irradiation.
本発明により、高感度および繰り返し使用時に
安定であり、フオトメモリー性の良好な、安定し
た良質の画像を提供する電子写真感光体が得られ
た。
ADVANTAGE OF THE INVENTION According to the present invention, an electrophotographic photoreceptor that has high sensitivity, is stable during repeated use, has good photomemory properties, and provides stable, high-quality images has been obtained.
Claims (1)
層を積層してなる電子写真感光体において、電荷
発生層がτ，τ′，ηおよびη′型無金属フタロシア
ニンから選ばれる少なくとも一種の無金属フタロ
シアニンを含有し、電荷移動層が下記一般式
〔〕で示される化合物を含有することを特徴と
する電子写真感光体。 一般式〔〕 （式中、R1，R2は、水素原子、アルキル基、
アルコキシ基またはアリール基、R3，R4，R5は
水素原子または−NR1（R2）基を示し、ｎは０ま
たは１である。） ２ 導電性支持体に、電荷発生層および電荷移動
層を積層してなる電子写真感光体において、電荷
発生層が、τ，τ′，ηおよびη′型無金属フタロシ
アニンから選ばれる少なくとも一種の無金属フタ
ロシアニンを含有し、電荷移動層が下記一般式
〔〕で示される化合物および下記一般式〔〕
で示される化合物を共に含有することを特徴とす
る電子写真感光体。 一般式〔〕 （式中、R1，R2は、水素原子、アルキル基、
アルコキシ基またはアリール基、R3、R4，R5は
水素原子または−NR1（R2）基を示し、ｎは０ま
たは１である。） 一般式〔〕 （式中、R6はアルキル基、アリール基を示し、
R1およびR2は、上記と同じ意味を表す。）[Scope of Claims] 1. An electrophotographic photoreceptor comprising a charge generation layer and a charge transfer layer laminated on a conductive support, wherein the charge generation layer is selected from τ, τ', η and η' type metal-free phthalocyanines. 1. An electrophotographic photoreceptor comprising at least one metal-free phthalocyanine containing at least one metal-free phthalocyanine, and a charge transfer layer containing a compound represented by the following general formula []. General formula [] (In the formula, R 1 and R 2 are hydrogen atoms, alkyl groups,
The alkoxy group or aryl group, R 3 , R 4 and R 5 represent a hydrogen atom or a -NR 1 (R 2 ) group, and n is 0 or 1. ) 2 In an electrophotographic photoreceptor comprising a charge generation layer and a charge transfer layer laminated on a conductive support, the charge generation layer comprises at least one type of metal-free phthalocyanine selected from τ, τ', η and η' type metal-free phthalocyanines. Compounds containing metal-free phthalocyanine and having a charge transfer layer represented by the following general formula [] and the following general formula []
An electrophotographic photoreceptor characterized by containing a compound represented by: General formula [] (In the formula, R 1 and R 2 are hydrogen atoms, alkyl groups,
The alkoxy group or aryl group, R 3 , R 4 and R 5 represent a hydrogen atom or a -NR 1 (R 2 ) group, and n is 0 or 1. ) General formula [] (In the formula, R 6 represents an alkyl group or an aryl group,
R 1 and R 2 have the same meanings as above. )
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4465387A JPS63210941A (en) | 1987-02-27 | 1987-02-27 | Electrophotographic sensitive body |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4465387A JPS63210941A (en) | 1987-02-27 | 1987-02-27 | Electrophotographic sensitive body |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63210941A JPS63210941A (en) | 1988-09-01 |
| JPH0435756B2 true JPH0435756B2 (en) | 1992-06-12 |
Family
ID=12697405
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4465387A Granted JPS63210941A (en) | 1987-02-27 | 1987-02-27 | Electrophotographic sensitive body |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63210941A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02134647A (en) * | 1988-11-15 | 1990-05-23 | Somar Corp | Laminated electrophotographic sensitive body |
| JPH03223763A (en) * | 1990-01-30 | 1991-10-02 | Tomoegawa Paper Co Ltd | Manufacture of laminate type organic photosensitive body |
| JP2870985B2 (en) * | 1990-05-22 | 1999-03-17 | 日本電気株式会社 | Electrophotographic photoreceptor |
-
1987
- 1987-02-27 JP JP4465387A patent/JPS63210941A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS63210941A (en) | 1988-09-01 |
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