JPH0519701B2 - - Google Patents
Info
- Publication number
- JPH0519701B2 JPH0519701B2 JP17019185A JP17019185A JPH0519701B2 JP H0519701 B2 JPH0519701 B2 JP H0519701B2 JP 17019185 A JP17019185 A JP 17019185A JP 17019185 A JP17019185 A JP 17019185A JP H0519701 B2 JPH0519701 B2 JP H0519701B2
- Authority
- JP
- Japan
- Prior art keywords
- charge
- layer
- photoreceptor
- electrophotographic photoreceptor
- styryl
- 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 - Lifetime
Links
- 108091008695 photoreceptors Proteins 0.000 claims description 53
- -1 styryl compound Chemical class 0.000 claims description 34
- 239000000463 material Substances 0.000 claims description 29
- 229920005989 resin Polymers 0.000 claims description 18
- 239000011347 resin Substances 0.000 claims description 18
- 239000011230 binding agent Substances 0.000 claims description 17
- 239000000758 substrate Substances 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000005504 styryl group Chemical group 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 2
- 239000010410 layer Substances 0.000 description 56
- 239000000049 pigment Substances 0.000 description 15
- 230000035945 sensitivity Effects 0.000 description 10
- 239000011248 coating agent Substances 0.000 description 8
- 238000000576 coating method Methods 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- 229920000178 Acrylic resin Polymers 0.000 description 4
- 239000004925 Acrylic resin Substances 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 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 4
- 229920001225 polyester resin Polymers 0.000 description 4
- 239000004645 polyester resin Substances 0.000 description 4
- 229920001187 thermosetting polymer Polymers 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 229910052711 selenium Inorganic materials 0.000 description 3
- 239000011669 selenium Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- QNLZIZAQLLYXTC-UHFFFAOYSA-N 1,2-dimethylnaphthalene Chemical compound C1=CC=CC2=C(C)C(C)=CC=C21 QNLZIZAQLLYXTC-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 229920000877 Melamine resin Polymers 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 compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 206010034972 Photosensitivity reaction Diseases 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N acrylaldehyde Natural products C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 239000002800 charge carrier Substances 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 150000004714 phosphonium salts Chemical class 0.000 description 2
- 230000036211 photosensitivity Effects 0.000 description 2
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 2
- 229920005668 polycarbonate resin Polymers 0.000 description 2
- 239000004431 polycarbonate resin Substances 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical compound C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 2
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- OIAQMFOKAXHPNH-UHFFFAOYSA-N 1,2-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1 OIAQMFOKAXHPNH-UHFFFAOYSA-N 0.000 description 1
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- VHQGURIJMFPBKS-UHFFFAOYSA-N 2,4,7-trinitrofluoren-9-one Chemical compound [O-][N+](=O)C1=CC([N+]([O-])=O)=C2C3=CC=C([N+](=O)[O-])C=C3C(=O)C2=C1 VHQGURIJMFPBKS-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 1
- VYWYYJYRVSBHJQ-UHFFFAOYSA-N 3,5-dinitrobenzoic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 VYWYYJYRVSBHJQ-UHFFFAOYSA-N 0.000 description 1
- DNXUGBMARDFRGG-UHFFFAOYSA-N 3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile Chemical compound O=C1C=CC(=O)C(C#N)=C1C#N DNXUGBMARDFRGG-UHFFFAOYSA-N 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
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 1
- 235000000177 Indigofera tinctoria Nutrition 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 239000004419 Panlite Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- 229920002433 Vinyl chloride-vinyl acetate copolymer Polymers 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 229910021417 amorphous silicon Inorganic materials 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 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
- 229910052980 cadmium sulfide Inorganic materials 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- 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 1
- 235000021240 caseins Nutrition 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- ZXJXZNDDNMQXFV-UHFFFAOYSA-M crystal violet Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1[C+](C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 ZXJXZNDDNMQXFV-UHFFFAOYSA-M 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- OSPMLGKXWXDPNO-UHFFFAOYSA-M disodium azanide hydroxide Chemical compound [Na+].[OH-].N[Na] OSPMLGKXWXDPNO-UHFFFAOYSA-M 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 1
- 239000005038 ethylene vinyl acetate Substances 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229940097275 indigo Drugs 0.000 description 1
- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229920000554 ionomer Polymers 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 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 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 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 1
- INAAIJLSXJJHOZ-UHFFFAOYSA-N pibenzimol Chemical compound C1CN(C)CCN1C1=CC=C(N=C(N2)C=3C=C4NC(=NC4=CC=3)C=3C=CC(O)=CC=3)C2=C1 INAAIJLSXJJHOZ-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 150000003071 polychlorinated biphenyls Chemical group 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 229940043267 rhodamine b Drugs 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 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
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- AUHHYELHRWCWEZ-UHFFFAOYSA-N tetrachlorophthalic anhydride Chemical compound ClC1=C(Cl)C(Cl)=C2C(=O)OC(=O)C2=C1Cl AUHHYELHRWCWEZ-UHFFFAOYSA-N 0.000 description 1
- NLDYACGHTUPAQU-UHFFFAOYSA-N tetracyanoethylene Chemical group N#CC(C#N)=C(C#N)C#N NLDYACGHTUPAQU-UHFFFAOYSA-N 0.000 description 1
- PCCVSPMFGIFTHU-UHFFFAOYSA-N tetracyanoquinodimethane Chemical compound N#CC(C#N)=C1C=CC(=C(C#N)C#N)C=C1 PCCVSPMFGIFTHU-UHFFFAOYSA-N 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 239000001016 thiazine dye Substances 0.000 description 1
- 239000001003 triarylmethane dye Substances 0.000 description 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical class C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 1
- 239000001018 xanthene dye 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
-
- 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
- G03G5/0601—Acyclic or carbocyclic compounds
- G03G5/0605—Carbocyclic compounds
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Photoreceptors In Electrophotography (AREA)
Description
産業上の利用分野
本発明は電子写真感光体に関し、さらに詳しく
は、スチリル化合物を主成分とする感光層を有す
る電子写真感光体に関する。
従来の技術と問題点
電子写真感光体として、導電性支持体上に電荷
発生層と電荷輸送層を積層してなる機能分離型
と、光導電性粒子を樹脂中に分散させた光導電層
を支持体上に形成してなる分散型が、広く知られ
ている。
機能分離型においては電荷キヤリアの発生とそ
の輸送という感光体における基本的機能を別個の
物質に分担せしめることにより、表面電位が高
く、電荷保持力が大きく、光感度が高く、繰り返
し特性が安定した感光層を得ることができる。機
能分離型の電荷発生用の電荷発生材料、電荷輸送
用の電荷輸送材料はともに多数の化合物が有効で
あることが知られている。例えば電荷輸送層とし
て、低分子の有機光導電体を用いたものが、数多
く提案されている。しかし、米国特許第3189447
号公報に記載されている２，５−ビス（Ｐ−ジエ
チルアミノフエニル）−１，３，４−オキサジア
ゾールを用いたものは、結着剤に対する相溶性が
低く、結晶が析出しやすい。また、米国特許第
3820989号公報に記載されているジアリールアル
カン誘導体を用いたものは、結着剤に対する相溶
性は良好であるが、繰り返し使用した場合に感度
変化が生じる等、未だ初期の感度及び残留電位特
性、繰り返し使用した場合の感度変化や耐久性に
ついて、大きく改善すべき点がある。
問題点を解決するための手段
本発明は上記従来における欠点を解消し、光感
度が高く、繰り返し使用を行つても電子写真特性
の安定している電子写真感光体を提供することを
目的とする。
即ち、本発明の要旨は導電性基体上に少なくと
も電荷発生材料と電荷輸送材料とを含有する感光
層を形成した電子写真感光体において、前記電荷
輸送材料として下記一般式［］で表されるスチ
リル化合物を含有することを特徴とする電子写真
感光体に関する；
［式中、Ar1，Ar2，Ar3及びAr4はそれぞれ置
換基を有してもよいアリール基を示し、Ar1〜
Ar4の少なくとも１つは置換基として置換アミノ
基を有するアリール基である。ｎは０又は１を示
す。］
Ar1，Ar2，Ar3，Ar4のうち少なくとも１つは
置換基を有することが好ましい。係る置換基とし
てジ置換アミノ基を有しており、
具体的には機能分離型の積層感光体にあつては
電荷輸送層に、分散型の単層感光体にあつては光
導電層に上記一般式〔〕で表わされるスチリル
化合物を感度の上昇と光疲労抑制のために含有す
る。
本発明一般式〔〕で表わされるスチリル化合
物の好ましい具体例としては、例えば次の構造式
を有するものが挙げられるが、これに限定される
ものではない。
本発明の一般式〔〕で表わされるスチリル化
合物は、公知の方法で容易に製造することができ
る。一般式［］で表わされるスチリル化合物
は、例えば下記一般式〔Ａ〕：
〔式中Ar1，Ar2は〔〕と同意義、R1，R2は
ホスホニウム塩を形成するアルキル基、シクロア
ルキル基、アラルキル基、アリール基を示す。〕
で表わされるリン化合物を下記一般式〔Ｂ〕：
一般式：
〔式中Ar3，Ar4は〔〕と同意義〕で表わさ
れるアクロレイン化合物と縮合させることにより
得られる。一般式〔Ａ〕で表わされるアクロレイ
ン化合物と縮合させることにより得られる。一般
式〔Ａ〕で表わされるリン化合物のR1，R2は、
特にシクロヘキシル基、ベンジル基、フエニル
基、低級アルキル基が好ましい。
上記方法における反応溶媒としては、例えば炭
化水素、アルコール類、エーテル類が良好で、メ
タノール、エタノール、イソプロパノール、ブタ
ノール、２−メトキシエタノール、１，２−ジメ
トキシエタン、ビス（２−メトキシエチル）エー
テル、ジオキサン、テトラヒドロフラン、トルエ
ン、キシレンジメチルスルホキシド、Ｎ，Ｎ−ジ
メチルホルムアミド、Ｎ−メチルピロリドン、
１，３−ジメチル−２−イミダゾリジノンなどが
挙げられる。中でも極性溶媒、例えばＮ，Ｎ−ジ
メチルホルムアミド及びジメチルスルホキシドが
好適である。
縮合剤としては苛性ソーダ、苛性カリ、ナトリ
ウムアミド水素ナトリウム及びナトリウムメチラ
ート、カリウム−ｔ−ブトキシドなどのアルコラ
ートが用いられる。
反応温度は約０℃〜約100℃まで広範囲に選択
することが出来る。好ましくは10℃〜80℃であ
る。
又、本発明によつて使用する化合物〔Ｃ〕はリ
ン化合物のかわりに対応する第４ホスホニウム
塩、例えばトリフエニルホスホニウム塩を使用
し、wittigの方法によりホスホリレンの段階を経
て、アルデヒド化合物〔Ｄ〕と縮合することによ
つて得られる。これらのスチリル化合物は単独で
用いても混合して用いてもよい。
本発明のスチリル化合物を用いた電子写真感光
体の構成例を第１図から第５図に模式的に示す。
第１図は、基体１上に光導電性材料３と電荷輸
送材料２を結着剤に配合した感光層４が形成され
た感光体であり、電荷輸送材料として本発明のス
チリル化合物が用いられている。
第２図は、感光層として電荷発生層６と電荷輸
送層５を有する機能分離型感光体であり、電荷発
生層６の表面に電荷輸送層５が形成されている。
電荷輸送層５中に本発明のスチリル化合物が配合
されている。
第３図は、第２図と同様電荷発生層６と電荷輸
送層５を有する機能分離型感光体であるが、第２
図とは逆に電荷輸送層５の表面に電荷発生層が形
成されている。
第４図は、第１図の感光体の表面にさらに表面
保護層７を設けたものであり、感光層４は電荷発
生層６と電荷輸送層５に分離した機能分離型とし
てもよい。
第５図は、基体１と感光層４の間に中間層８を
設けたものであり、中間層８は接着性の改善、塗
工性の向上、基体の保護、基体からの光導電層へ
の電荷注入性改善のために設けることができる。
中間層としては、ポイリミド樹脂、ポリエステル
樹脂、ポリビニルブチラール樹脂、カゼイン等を
用いるとよい。この態様の感光体も感光層を機能
分離型としてもよい。
本発明の電子写真用感光体は、一般式〔〕で
表わされるスチリル化合物をバインダーと共に適
当な溶剤中に溶解あるいは分散し、必要に応じ光
導電性材料と電子吸引性化合物、あるいは増感染
料、その他の顔料を添加して得られる塗布液を導
電性基体上に塗布、乾燥し、通常５〜30μm、好
ましくは６〜20μmの膜厚の感光層を形成させる
ことにより製造することができる。
具体的には、導電性支持体上に電荷発生層と電
荷輸送層を積層してなり、前述した第２図の感光
体と同様の構成である機能分離型感光体は、導電
性支持体上に電荷発生材料を真空蒸着するか、適
当な溶剤もしくは必要があれば、バインダー樹脂
を溶解させた溶液中に分散させて作製した塗布液
を塗布、乾燥して電荷発生層を形成しその上に電
荷輸送材料としてスチリル化合物とバインダー樹
脂とを適当な溶剤に溶解させた溶液を塗布乾燥し
電荷輸送層を形成して得られる。このときの電荷
発生層の厚みは4μm以下、好ましくは2μm以下で
あり、電荷輸送層の厚みは３〜30μm、好ましく
は５〜20μmがよい。電荷輸送層中のスチリル化
合物の割合はバインダー樹脂１重量部に対し0.02
〜２重量部、好ましくは0.03〜1.3重量部とする
のが好適である。また、他の電荷輸送材を組み合
わせてもよい。それ自身バインダーとして使用で
きる高分子電荷輸送材料の場合は、他のバインダ
ーを使用しなくてもよい。感光体の構成は、前述
した第３図の感光体と同様に、導電性支持体上に
電荷輸送層を形成し、その上に電荷発生層を積層
した構成でもよい。
導電性支持体上に光導電層を形成して成り、前
述した第１図の感光体と同様の構成である分散型
感光体は、光導電性材料の微粒子をスチリル化合
物とバインダー樹脂を溶解した溶液中に分散さ
せ、これを導電性支持体上に塗布、乾燥して光導
電層を形成して得られる。このときの光導電層の
厚さは、３〜30μm、好ましくは５〜20μmがよ
い。使用する光導電性材料の量が少なすぎると感
度が悪く、多すぎると帯電性が悪くなつたり、光
導電層の強度が弱くなつたりし、光導電層中の光
導電性材料の量は、樹脂１重量部に対して0.01〜
２重量部、好ましくは0.05〜１重量部がよく、ス
チリル化合物の割合は樹脂１重量部に対し、0.01
〜２重量部、好ましくは0.02〜1.2重量部が好適
である。また、それ自身バインダーとして使用で
きるポリビニルカルバゾールなどの高分子光導電
体と併用してもよい。また、他の電荷輸送材料、
たとえばヒドラゾン化合物と組み合わせてもよ
い。
本発明電子写真感光体の機能分離型における電
荷発生材料、分散型における光導電性材料として
用いられるものは、ビスアゾ顔料、トリアリール
メタン系染料、チアジン系染料、オキサジン系染
料、キサンテン系染料、シアニン系色素、スチリ
ル系色素、ピリリウム系染料、アゾ系顔料、キナ
クリドン系顔料、インジゴ系顔料、ペリレン系顔
料、多環キノン系顔料、ビスベンズイミダゾール
系顔料、インダスロン系顔料、スクアリリウム系
顔料、フタロシアニン系顔料等の有機物質やセレ
ン、セレン・テルル、セレン・ヒ素、硫化カドミ
ウム、アモルフアスシリコン等の無機物質があげ
られる。これ以外も、光吸収し極めて高い効率で
電荷担体を発生する材料であれば、いずれの材料
であつても使用することができる。
また、バインダーとして使用できるものは、電
気絶縁性でありそれ自体公知の熱可塑性樹脂ある
いは熱硬化性樹脂や光硬化性樹脂、光導電性樹脂
も全て使用することができる。適当なバインダー
樹脂の例は、これに限定されるものではないが、
飽和ポリエステル樹脂、ポリアミド樹脂、アクリ
ル樹脂、エチレン−酢酸ビニル共重合体、イオン
架橋オレフイン共重合体（アイオノマー）、スチ
レン−ブタジエンブロツク共重合体、ポリアリレ
ート、ポリカーボネート、塩化ビニル−酢酸ビニ
ル共重合体、セルロースエステル、ポリイミド、
スチロール樹脂等の熱可塑性結着剤；エポキシ樹
脂、ウレタン樹脂、シリコーン樹脂、フエノール
樹脂、メラミン樹脂、キシレン樹脂、アルキツド
樹脂、熱硬化性アクリル樹脂等の熱硬化性結着
剤；光硬化性樹脂；ポリ−Ｎ−ビニルカルバゾー
ル、ポリビニルピレン、ポリビニルアントラセン
等の光導電性樹脂等である。これらは単独で、ま
たは組み合わせて使用することができる。これら
電気絶縁性樹脂は単独で測定して１×1012Ω・cm
以上の体積抵抗を有することが望ましい。より好
ましいものとしてはポリエステル樹脂、ポリカー
ボネート、アクリル樹脂である。
本発明の電子写真感光体はバインダーととも
に、ハロゲン化パラフイン、ポリ塩化ビフエニ
ル、ジメチルナフタレン、ジブチルフタレート、
ｏ−ターフエニルなどの可塑剤や、クロラニル、
テトラシアノエチレン、２，４，７−トリニトロ
−９−フルオレノン、５，６−ジシアノベンゾキ
ノン、テトラシアノキノジメタン、テトラクロル
無水フタル酸、３，５−ジニトロ安息香酸等の電
子吸引性増感剤、メチルバイオレツト、ローダミ
ンＢ、シアニン染料、ピリリウム塩、チアピリリ
ウム塩等の増感剤を使用してもよい。
この様にして形成される電子写真感光体は、前
述した第４図及び第５図のように必要に応じて接
着層、中間層、表面保護層を有していてもよい。
以上のように本発明スチリル化合物は容易に製
造可能で、それを含む感光体は、機能分離型とし
ても分散型としても使用でき、また種々の電荷発
生材料及びバインダー樹脂との組み合わせが可能
であり、場合によつては他の電荷輸送材料を加え
ることができる。したがつて本発明スチリル化合
物を含有する電子写真感光体は、きわめて製造容
易で使用範囲が広く、且つスチリル化合物によつ
て光疲労を有効に防止して繰り返し特性に優れた
ものとなり、感度が向上し、表面電位変化が少な
いものとなる。
実施例 １
下記化学式〔〕で表わされるビスアゾ顔料２
部、ポリエステル樹脂（バイロン200；東洋紡(株)
製）１部、メチルエチルケトン100部、をボール
ミルポツトに入れて24時間分散し、感光塗液を得
た。これをアルミニウム基体上に塗布、乾燥し、
厚さ0.3μの電荷発生層を形成させた。
化学式：
この電荷発生層の上にスチリル化合物(2)を10
部、ポリカーボネート樹脂（パンライトＫ−
1300；帝人化成(株)製）を10部、テトラヒドロフラ
ン80部に溶解させた塗布液を、乾燥後の膜厚が
15μとなるように塗布して、電荷輸送層を形成さ
せ、感光体１を作製した。
こうして作製した感光体１を、市販の電子写真
複写機（ミノルタカメラ(株)製；EP−450Z）に組
み込み、直流電源を−6KVに印加し、初期表面
電位（Vp（ｖ））およびVpが1/2の電位になるまで
に要した露光量（E1/2（lux・sec））、帯電後１秒
間暗所に放置した後の電位の減衰率（DDR1
（％））残留電位（VR（ｖ））を測定した。
実施例 ２
銅フタロシアニン50部とテトラニトロ銅フタロ
シアニン0.2部を、98％濃硫酸500部に十分攪拌し
ながら溶解させ、これを水5000部にあけ、銅フタ
ロシアニンとテトラニトロ銅フタロシアニンの光
導電性材料組成物を析出させた後、ろ過、水洗
し、減圧下120℃で乾燥した。
得られた組成物10部を、熱硬化性アクリル樹脂
（アクリデイツクA405；大日本インキ(株)製）22.5
部、メラミン樹脂（スーパーベツカミンJ820；大
日本インキ(株)製）7.5部、スチリル化合物(2)15部
をメチルイソブチルケトンとセロソルブアセテー
トを同量に混合した混合溶剤70部とともに、ポー
ルミルポツトに入れて48時間分散し、光導電性塗
料を調整し、この塗料をアルミニウム基体上に約
15μとなるように塗布し、乾燥させて感光体２を
作製した。
また感光体３，４，５として上記と同様の方法
で同一の構成のもの、但し電荷輸送層のスチリル
化合物(2)の代わりに、スチリル化合物(3)，(4)，(6)
を夫々含む感光体を作製した。
こうして作製した感光体２，３，４，５のVp，
E1/2，DDR1，VRを実施例１と同様の方法で、但
し直流電源に印加する電圧を＋6KVとして測定
した。
実施例１，２で得られた感光体１〜５のVp，
E1/2，DDR1，VRの測定結果は第１表に示す通り
である。
INDUSTRIAL APPLICATION FIELD The present invention relates to an electrophotographic photoreceptor, and more particularly to an electrophotographic photoreceptor having a photosensitive layer containing a styryl compound as a main component. Conventional Technologies and Problems As electrophotographic photoreceptors, there are two types: a functionally separated type in which a charge generation layer and a charge transport layer are laminated on a conductive support, and a photoconductive layer in which photoconductive particles are dispersed in a resin. A dispersed type formed on a support is widely known. In the functionally separated type, the basic functions of the photoreceptor, namely generation and transport of charge carriers, are assigned to separate substances, resulting in high surface potential, large charge retention, high photosensitivity, and stable repeatability. A photosensitive layer can be obtained. It is known that a large number of compounds are effective for both functionally separated charge generation materials for charge generation and charge transport materials for charge transport. For example, many charge transport layers using low-molecular organic photoconductors have been proposed. However, U.S. Patent No. 3189447
The one using 2,5-bis(P-diethylaminophenyl)-1,3,4-oxadiazole described in the publication has low compatibility with the binder and tends to precipitate crystals. Additionally, U.S. Patent No.
The diaryl alkane derivative described in Publication No. 3820989 has good compatibility with the binder, but it still has initial sensitivity and residual potential characteristics, such as changes in sensitivity when used repeatedly, and problems with repeated use. There are major improvements to be made in terms of sensitivity changes and durability during use. Means for Solving the Problems The present invention aims to eliminate the above-mentioned conventional drawbacks and provide an electrophotographic photoreceptor that has high photosensitivity and stable electrophotographic characteristics even after repeated use. . That is, the gist of the present invention is to provide an electrophotographic photoreceptor in which a photosensitive layer containing at least a charge-generating material and a charge-transporting material is formed on a conductive substrate, and a styryl represented by the following general formula [] as the charge-transporting material. Regarding an electrophotographic photoreceptor characterized by containing a compound; [In the formula, Ar 1 , Ar 2 , Ar 3 and Ar 4 each represent an aryl group which may have a substituent, and Ar 1 to
At least one of Ar 4 is an aryl group having a substituted amino group as a substituent. n represents 0 or 1. ] It is preferable that at least one of Ar 1 , Ar 2 , Ar 3 , and Ar 4 has a substituent. It has a di-substituted amino group as such a substituent, and specifically, it is added to the charge transport layer in the case of a function-separated layered photoreceptor, and the photoconductive layer in the case of a dispersed type single-layer photoreceptor. A styryl compound represented by the general formula [] is contained to increase sensitivity and suppress optical fatigue. Preferred specific examples of the styryl compound represented by the general formula [ ] of the present invention include, for example, those having the following structural formula, but are not limited thereto. The styryl compound represented by the general formula [] of the present invention can be easily produced by a known method. The styryl compound represented by the general formula [] is, for example, the following general formula [A]: [In the formula, Ar 1 and Ar 2 have the same meaning as [], and R 1 and R 2 represent an alkyl group, a cycloalkyl group, an aralkyl group, or an aryl group that forms a phosphonium salt. ]
The phosphorus compound represented by the following general formula [B]: General formula: It can be obtained by condensation with an acrolein compound represented by [where Ar 3 and Ar 4 have the same meaning as []]. It is obtained by condensation with an acrolein compound represented by the general formula [A]. R 1 and R 2 of the phosphorus compound represented by the general formula [A] are:
Particularly preferred are cyclohexyl group, benzyl group, phenyl group, and lower alkyl group. Preferred reaction solvents in the above method include, for example, hydrocarbons, alcohols, and ethers, including methanol, ethanol, isopropanol, butanol, 2-methoxyethanol, 1,2-dimethoxyethane, bis(2-methoxyethyl) ether, Dioxane, tetrahydrofuran, toluene, xylene dimethyl sulfoxide, N,N-dimethylformamide, N-methylpyrrolidone,
Examples include 1,3-dimethyl-2-imidazolidinone. Among them, polar solvents such as N,N-dimethylformamide and dimethylsulfoxide are preferred. As the condensing agent, caustic soda, caustic potash, sodium amide sodium hydroxide, and alcoholates such as sodium methylate and potassium t-butoxide are used. The reaction temperature can be selected over a wide range from about 0°C to about 100°C. Preferably it is 10°C to 80°C. Further, the compound [C] used in the present invention is converted into an aldehyde compound [D] by using a corresponding quaternary phosphonium salt, such as a triphenylphosphonium salt, in place of the phosphorus compound, and passing through the phosphorylene stage according to the method of Whittig. It can be obtained by condensation with These styryl compounds may be used alone or in combination. Examples of the structure of an electrophotographic photoreceptor using the styryl compound of the present invention are schematically shown in FIGS. 1 to 5. FIG. 1 shows a photoreceptor in which a photosensitive layer 4 containing a photoconductive material 3 and a charge transporting material 2 as a binder is formed on a substrate 1, and the styryl compound of the present invention is used as the charge transporting material. ing. FIG. 2 shows a functionally separated photoreceptor having a charge generation layer 6 and a charge transport layer 5 as photosensitive layers, and the charge transport layer 5 is formed on the surface of the charge generation layer 6.
The styryl compound of the present invention is blended into the charge transport layer 5. FIG. 3 shows a functionally separated photoreceptor having a charge generation layer 6 and a charge transport layer 5 as in FIG.
Contrary to the figure, a charge generation layer is formed on the surface of the charge transport layer 5. In FIG. 4, a surface protective layer 7 is further provided on the surface of the photoreceptor shown in FIG. 1, and the photosensitive layer 4 may be of a functionally separated type in which a charge generation layer 6 and a charge transport layer 5 are separated. FIG. 5 shows an intermediate layer 8 provided between the substrate 1 and the photosensitive layer 4. The intermediate layer 8 is used to improve adhesion, improve coatability, protect the substrate, and protect the photoconductive layer from the substrate. It can be provided to improve charge injection properties.
As the intermediate layer, polyimide resin, polyester resin, polyvinyl butyral resin, casein, etc. may be used. The photoreceptor of this embodiment may also have a photosensitive layer of a functionally separated type. The electrophotographic photoreceptor of the present invention can be prepared by dissolving or dispersing a styryl compound represented by the general formula [] in a suitable solvent together with a binder, and optionally adding a photoconductive material and an electron-withdrawing compound, or a sensitizing dye, It can be produced by applying a coating solution obtained by adding other pigments onto a conductive substrate and drying it to form a photosensitive layer having a thickness of usually 5 to 30 μm, preferably 6 to 20 μm. Specifically, a functionally separated photoreceptor has a structure similar to that of the photoreceptor shown in FIG. The charge-generating material is vacuum-deposited on the surface, or a coating solution prepared by dispersing the charge-generating material in a suitable solvent or, if necessary, a solution containing a binder resin, is applied and dried to form a charge-generating layer. A charge transporting layer is obtained by coating a solution of a styryl compound and a binder resin dissolved in a suitable solvent as a charge transporting material, and drying the coating to form a charge transporting layer. The thickness of the charge generation layer at this time is 4 μm or less, preferably 2 μm or less, and the thickness of the charge transport layer is 3 to 30 μm, preferably 5 to 20 μm. The proportion of styryl compound in the charge transport layer is 0.02 parts by weight of binder resin.
-2 parts by weight, preferably 0.03-1.3 parts by weight. Further, other charge transport materials may be used in combination. In the case of polymeric charge transport materials that can themselves be used as binders, no other binder may be used. The structure of the photoreceptor may be similar to the photoreceptor shown in FIG. 3 described above, in which a charge transport layer is formed on a conductive support, and a charge generation layer is laminated thereon. A dispersion type photoreceptor, which is composed of a photoconductive layer formed on a conductive support and has a structure similar to that of the photoreceptor shown in FIG. It is obtained by dispersing it in a solution, coating it on a conductive support, and drying it to form a photoconductive layer. The thickness of the photoconductive layer at this time is preferably 3 to 30 μm, preferably 5 to 20 μm. If the amount of photoconductive material used is too small, the sensitivity will be poor, and if it is too large, the charging property will be poor or the strength of the photoconductive layer will be weakened. 0.01 to 1 part by weight of resin
2 parts by weight, preferably 0.05 to 1 part by weight, and the proportion of the styryl compound is 0.01 parts by weight per 1 part by weight of resin.
~2 parts by weight, preferably 0.02 to 1.2 parts by weight are suitable. It may also be used in combination with a polymeric photoconductor such as polyvinylcarbazole, which itself can be used as a binder. Also, other charge transport materials,
For example, it may be combined with a hydrazone compound. The charge-generating materials used in the functionally separated type electrophotographic photoreceptor of the present invention and the photoconductive materials used in the dispersed type include bisazo pigments, triarylmethane dyes, thiazine dyes, oxazine dyes, xanthene dyes, and cyanine. pigments, styryl pigments, pyrylium dyes, azo pigments, quinacridone pigments, indigo pigments, perylene pigments, polycyclic quinone pigments, bisbenzimidazole pigments, induthrone pigments, squarylium pigments, phthalocyanine pigments Examples include organic substances such as pigments and inorganic substances such as selenium, selenium/tellurium, selenium/arsenic, cadmium sulfide, and amorphous silicon. In addition to this, any material can be used as long as it absorbs light and generates charge carriers with extremely high efficiency. Further, as the binder, any electrically insulating and well-known thermoplastic resin, thermosetting resin, photocuring resin, or photoconductive resin can be used. Examples of suitable binder resins include, but are not limited to:
Saturated polyester resin, polyamide resin, acrylic resin, ethylene-vinyl acetate copolymer, ionically crosslinked olefin copolymer (ionomer), styrene-butadiene block copolymer, polyarylate, polycarbonate, vinyl chloride-vinyl acetate copolymer, cellulose ester, polyimide,
Thermoplastic binders such as styrene resins; thermosetting binders such as epoxy resins, urethane resins, silicone resins, phenol resins, melamine resins, xylene resins, alkyd resins, thermosetting acrylic resins; photocurable resins; These include photoconductive resins such as poly-N-vinylcarbazole, polyvinylpyrene, and polyvinylanthracene. These can be used alone or in combination. These electrically insulating resins have a resistance of 1×10 12 Ω・cm when measured individually.
It is desirable to have a volume resistivity equal to or higher than that. More preferred are polyester resin, polycarbonate, and acrylic resin. In addition to the binder, the electrophotographic photoreceptor of the present invention includes halogenated paraffin, polychlorinated biphenyl, dimethylnaphthalene, dibutyl phthalate,
Plasticizers such as o-terphenyl, chloranil,
Electron-withdrawing sensitizers such as tetracyanoethylene, 2,4,7-trinitro-9-fluorenone, 5,6-dicyanobenzoquinone, tetracyanoquinodimethane, tetrachlorophthalic anhydride, 3,5-dinitrobenzoic acid, Sensitizers such as methyl violet, rhodamine B, cyanine dyes, pyrylium salts, thiapyrylium salts and the like may be used. The electrophotographic photoreceptor formed in this manner may have an adhesive layer, an intermediate layer, and a surface protection layer as required, as shown in FIGS. 4 and 5 described above. As described above, the styryl compound of the present invention can be easily produced, and a photoreceptor containing it can be used as a functionally separated type or a dispersed type, and can be combined with various charge-generating materials and binder resins. , and optionally other charge transport materials can be added. Therefore, the electrophotographic photoreceptor containing the styryl compound of the present invention is extremely easy to manufacture and can be used in a wide range of applications, and the styryl compound effectively prevents optical fatigue, resulting in excellent repeatability and improved sensitivity. However, the change in surface potential is small. Example 1 Bisazo pigment 2 represented by the following chemical formula []
Polyester resin (Byron 200; Toyobo Co., Ltd.)
Co., Ltd.) and 100 parts of methyl ethyl ketone were placed in a ball mill pot and dispersed for 24 hours to obtain a photosensitive coating liquid. Coat this on an aluminum substrate, dry it,
A charge generation layer with a thickness of 0.3μ was formed. Chemical formula: Add styryl compound (2) for 10 minutes on top of this charge generation layer.
part, polycarbonate resin (Panlite K-
1300 (manufactured by Teijin Kasei Ltd.) dissolved in 10 parts of tetrahydrofuran and 80 parts of tetrahydrofuran.
A charge transport layer was formed by coating to a thickness of 15μ, and photoreceptor 1 was prepared. The thus prepared photoreceptor 1 was installed in a commercially available electrophotographic copying machine (manufactured by Minolta Camera Co., Ltd.; EP-450Z), and a DC power supply of -6KV was applied to the initial surface potential (V p (v)) and V The amount of exposure required for p to reach 1/2 of the potential (E 1/2 (lux・sec)), the decay rate of potential after being left in the dark for 1 second after being charged (DDR 1
(%)) Residual potential (V R (v)) was measured. Example 2 50 parts of copper phthalocyanine and 0.2 parts of tetranitro copper phthalocyanine were dissolved in 500 parts of 98% concentrated sulfuric acid with thorough stirring, and this was poured into 5000 parts of water to prepare a photoconductive material composition of copper phthalocyanine and tetranitro copper phthalocyanine. After precipitating, it was filtered, washed with water, and dried at 120°C under reduced pressure. 10 parts of the obtained composition was mixed with 22.5 parts of a thermosetting acrylic resin (Acridik A405; manufactured by Dainippon Ink Co., Ltd.).
1 part, 7.5 parts of melamine resin (Supervecamine J820; manufactured by Dainippon Ink Co., Ltd.), 15 parts of styryl compound (2), and 70 parts of a mixed solvent containing equal amounts of methyl isobutyl ketone and cellosolve acetate were placed in a Pall mill pot. Disperse for 48 hours to prepare a photoconductive paint and apply this paint onto an aluminum substrate for approximately 48 hours.
A photoreceptor 2 was prepared by coating the film to a thickness of 15 μm and drying it. In addition, as photoreceptors 3, 4, and 5, the same structure was used in the same manner as above, except that styryl compounds (3), (4), and (6) were used instead of styryl compound (2) in the charge transport layer.
Photoreceptors containing each of these were prepared. V p of photoreceptors 2, 3, 4, and 5 prepared in this way,
E 1/2 , DDR 1 , and VR were measured in the same manner as in Example 1, except that the voltage applied to the DC power supply was +6 KV. V p of photoreceptors 1 to 5 obtained in Examples 1 and 2,
The measurement results for E 1/2 , DDR 1 , and VR are shown in Table 1.
【表】
いずれの感光体においても表面電位が大きく、
残留電位が小さく、高感度であることがわかる。
つまり、本発明のスチリル化合物を用いた感光体
は、機能分離型でも分散型でも使用でき、常に良
好な画像を得ることができる。
また複写機による正帯電の繰り返し実写テスト
を実施例２の感光体２，３，４，５において行つ
たが、10000枚のコピーにて初期、最終画像とも
階調性に優れ、感度変化がなく、繰り返し使用し
た場合でも電子写真特性が安定していた。
比較例 １
感光体６，７として実施例２の感光体２と同様
の方法で同一の構成のもの、但し電荷輸送層のス
チリル化合物(2)の代わりに、下記化学式［］、
［］で表わされる化合物を夫々含有する感光体
を作製した。
化学式：
化学式：
こうして作製した感光体６，７と実施例２にお
いて作製した感光体２のVp，Ｅ，DDR1，VRを実
施例２と同様の方法で測定した。測定結果は第２
表に示すとおりである。[Table] The surface potential of each photoreceptor is large;
It can be seen that the residual potential is small and the sensitivity is high.
In other words, the photoreceptor using the styryl compound of the present invention can be used in either a functionally separated type or a dispersed type, and can always provide good images. In addition, a photoconductor test of photoreceptors 2, 3, 4, and 5 of Example 2 was subjected to repeated positive charging tests using a copying machine, and after 10,000 copies, both the initial and final images had excellent gradation, and there was no change in sensitivity. The electrophotographic properties were stable even after repeated use. Comparative Example 1 The photoreceptors 6 and 7 were constructed in the same manner as the photoreceptor 2 of Example 2, except that the styryl compound (2) in the charge transport layer was replaced with the following chemical formula [],
Photoreceptors containing each of the compounds represented by [ ] were prepared. Chemical formula: Chemical formula: V p , E, DDR 1 , and VR of photoreceptors 6 and 7 thus prepared and photoreceptor 2 prepared in Example 2 were measured in the same manner as in Example 2. The measurement results are the second
As shown in the table.
【表】
第２表において感光体２は感光体６，７に比べ
てE1/2が著しく小さくスチリル化合物を含む感光
体２は高感度であることがわかる。
発明の効果
本発明化合物を用いて得られた電子写真感光体
は、光疲労を効果的に抑制し、繰り返し使用した
場合に表面電位の減少及び残留電位の上昇、感度
変化が少なく、電子写真特性が安定しており、高
感度なものであるため、鮮明な画像を得ることが
できる。[Table] In Table 2, it can be seen that photoreceptor 2 has a significantly smaller E 1/2 than photoreceptors 6 and 7, and photoreceptor 2 containing a styryl compound has high sensitivity. Effects of the Invention The electrophotographic photoreceptor obtained using the compound of the present invention effectively suppresses photofatigue, shows less decrease in surface potential, less increase in residual potential, and less change in sensitivity when used repeatedly, and has electrophotographic properties. Since it is stable and highly sensitive, it is possible to obtain clear images.
第１図〜第５図は、本発明に係る電子写真感光
体の模式図であつて、第１図，第４図，第５図は
導電性支持体上に光導電層を積層してなる分散型
感光体の構造を示し、第２図及び第３図は導電性
支持体上に電荷発生層と電荷輸送層を積層してな
る機能分離型感光体の構造を示す。
１……導電性基体、２……電荷輸送材料、３…
…光導電性材料、４……感光層、５……電荷輸送
層、６……光導電層、７……表面保護層、８……
中間層。
1 to 5 are schematic diagrams of an electrophotographic photoreceptor according to the present invention, in which FIGS. 1, 4, and 5 are formed by laminating a photoconductive layer on a conductive support. The structure of a dispersed photoreceptor is shown, and FIGS. 2 and 3 show the structure of a functionally separated photoreceptor in which a charge generation layer and a charge transport layer are laminated on a conductive support. 1... Conductive substrate, 2... Charge transport material, 3...
...Photoconductive material, 4...Photosensitive layer, 5...Charge transport layer, 6...Photoconductive layer, 7...Surface protection layer, 8...
middle class.
Claims (1)
荷輸送材料とを含有する感光層を形成した電子写
真感光体において、前記電荷輸送材料として下記
一般式［］で表されるスチリル化合物を含有す
ることを特徴とする電子写真感光体： ［式中、Ar1，Ar2，Ar3及びAr4はそれぞれ置
換基を有してもよいアリール基を示し、Ar1〜
Ar4の少なくとも１つは置換基として置換アミノ
基を有するアリール基である。ｎは０又は１を示
す。］ ２ 前記感光層が、電荷発生材料を含有する電荷
発生層と、前記スチリル化合物を含有する電荷輸
送層とからなることを特徴とする特許請求の範囲
第１項記載の電子写真感光体。 ３ 前記感光層が電荷発生材料と前記スチリル化
合物とをバインダー樹脂中に分散してなることを
特徴とする特許請求の範囲第１項記載の電子写真
感光体。[Scope of Claims] 1. An electrophotographic photoreceptor in which a photosensitive layer containing at least a charge-generating material and a charge-transporting material is formed on a conductive substrate, wherein the charge-transporting material is a styryl represented by the following general formula []. Electrophotographic photoreceptor characterized by containing a compound: [In the formula, Ar 1 , Ar 2 , Ar 3 and Ar 4 each represent an aryl group which may have a substituent, and Ar 1 to
At least one of Ar 4 is an aryl group having a substituted amino group as a substituent. n represents 0 or 1. 2. The electrophotographic photoreceptor according to claim 1, wherein the photosensitive layer comprises a charge generation layer containing a charge generation material and a charge transport layer containing the styryl compound. 3. The electrophotographic photoreceptor according to claim 1, wherein the photosensitive layer is formed by dispersing a charge generating material and the styryl compound in a binder resin.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17019185A JPS6230255A (en) | 1985-07-31 | 1985-07-31 | Electrophotographic sensitive body |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17019185A JPS6230255A (en) | 1985-07-31 | 1985-07-31 | Electrophotographic sensitive body |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6230255A JPS6230255A (en) | 1987-02-09 |
| JPH0519701B2 true JPH0519701B2 (en) | 1993-03-17 |
Family
ID=15900362
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17019185A Granted JPS6230255A (en) | 1985-07-31 | 1985-07-31 | Electrophotographic sensitive body |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6230255A (en) |
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-
1985
- 1985-07-31 JP JP17019185A patent/JPS6230255A/en active Granted
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| JP2008074714A (en) * | 2006-09-19 | 2008-04-03 | Takasago Internatl Corp | New charge transport material and electrophotographic photoreceptor using the same |
| WO2011013558A1 (en) | 2009-07-28 | 2011-02-03 | 保土谷化学工業株式会社 | Indole derivative |
| WO2011055756A1 (en) | 2009-11-06 | 2011-05-12 | 保土谷化学工業株式会社 | Diphenylnaphthylamine derivative |
| WO2012002227A1 (en) | 2010-06-29 | 2012-01-05 | 保土谷化学工業株式会社 | Triphenylamine derivative |
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| Publication number | Publication date |
|---|---|
| JPS6230255A (en) | 1987-02-09 |
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