JPS6155672B2 - - Google Patents
Info
- Publication number
- JPS6155672B2 JPS6155672B2 JP55038543A JP3854380A JPS6155672B2 JP S6155672 B2 JPS6155672 B2 JP S6155672B2 JP 55038543 A JP55038543 A JP 55038543A JP 3854380 A JP3854380 A JP 3854380A JP S6155672 B2 JPS6155672 B2 JP S6155672B2
- Authority
- JP
- Japan
- Prior art keywords
- photoreceptor
- bis
- resin
- resins
- charge
- 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
- 229920005989 resin Polymers 0.000 claims description 54
- 239000011347 resin Substances 0.000 claims description 54
- 108091008695 photoreceptors Proteins 0.000 claims description 48
- 229920001230 polyarylate Polymers 0.000 claims description 24
- 239000011230 binding agent Substances 0.000 claims description 17
- 239000002800 charge carrier Substances 0.000 claims description 3
- 239000002131 composite material Substances 0.000 claims 1
- 239000010410 layer Substances 0.000 description 24
- 230000035945 sensitivity Effects 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 11
- 239000011248 coating agent Substances 0.000 description 8
- 238000000576 coating method Methods 0.000 description 8
- -1 polypynylacetal Polymers 0.000 description 7
- 239000000975 dye Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000000049 pigment Substances 0.000 description 5
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 5
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 5
- 239000004926 polymethyl methacrylate Substances 0.000 description 5
- 229920005990 polystyrene resin Polymers 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000004721 Polyphenylene oxide Substances 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 4
- 238000005299 abrasion Methods 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 150000002894 organic compounds Chemical class 0.000 description 4
- 239000004014 plasticizer Substances 0.000 description 4
- 229920006380 polyphenylene oxide Polymers 0.000 description 4
- 239000001294 propane Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 229910052711 selenium Inorganic materials 0.000 description 4
- 239000011669 selenium Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WUPHOULIZUERAE-UHFFFAOYSA-N 3-(oxolan-2-yl)propanoic acid Chemical compound OC(=O)CCC1CCCO1 WUPHOULIZUERAE-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 229910052980 cadmium sulfide Inorganic materials 0.000 description 3
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 3
- 229910010272 inorganic material Inorganic materials 0.000 description 3
- 230000014759 maintenance of location Effects 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- NJWGQARXZDRHCD-UHFFFAOYSA-N 2-methylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC=C3C(=O)C2=C1 NJWGQARXZDRHCD-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 229910000967 As alloy Inorganic materials 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 229910001215 Te alloy Inorganic materials 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- QLNFINLXAKOTJB-UHFFFAOYSA-N [As].[Se] Chemical compound [As].[Se] QLNFINLXAKOTJB-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 239000011888 foil Substances 0.000 description 2
- 150000002484 inorganic compounds Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229940018564 m-phenylenediamine Drugs 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229920002492 poly(sulfone) 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
- 229920006267 polyester film Polymers 0.000 description 2
- GUEIZVNYDFNHJU-UHFFFAOYSA-N quinizarin Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC=C2O GUEIZVNYDFNHJU-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- FHIDEWWHKSJPTK-UHFFFAOYSA-N (3,5-dinitrophenyl)-phenylmethanone Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC(C(=O)C=2C=CC=CC=2)=C1 FHIDEWWHKSJPTK-UHFFFAOYSA-N 0.000 description 1
- YRTPZXMEBGTPLM-UVTDQMKNSA-N (3z)-3-benzylidene-2-benzofuran-1-one Chemical compound C12=CC=CC=C2C(=O)O\C1=C/C1=CC=CC=C1 YRTPZXMEBGTPLM-UVTDQMKNSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- GESUXCLRERRNSQ-UHFFFAOYSA-N 1-benzhydrylnaphthalene Chemical compound C1=CC=CC=C1C(C=1C2=CC=CC=C2C=CC=1)C1=CC=CC=C1 GESUXCLRERRNSQ-UHFFFAOYSA-N 0.000 description 1
- VOZLLWQPJJSWPR-UHFFFAOYSA-N 1-chloro-5-nitroanthracene-9,10-dione Chemical compound O=C1C2=C(Cl)C=CC=C2C(=O)C2=C1C=CC=C2[N+](=O)[O-] VOZLLWQPJJSWPR-UHFFFAOYSA-N 0.000 description 1
- FLIMNTJKWXTBRB-UHFFFAOYSA-N 1-ethenylanthracene;1-ethenyl-9h-carbazole Chemical compound C12=CC=CC=C2NC2=C1C=CC=C2C=C.C1=CC=C2C=C3C(C=C)=CC=CC3=CC2=C1 FLIMNTJKWXTBRB-UHFFFAOYSA-N 0.000 description 1
- YCANAXVBJKNANM-UHFFFAOYSA-N 1-nitroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2[N+](=O)[O-] YCANAXVBJKNANM-UHFFFAOYSA-N 0.000 description 1
- FBNAYEYTRHHEOB-UHFFFAOYSA-N 2,3,5-triphenyl-1,3-dihydropyrazole Chemical compound N1N(C=2C=CC=CC=2)C(C=2C=CC=CC=2)C=C1C1=CC=CC=C1 FBNAYEYTRHHEOB-UHFFFAOYSA-N 0.000 description 1
- SVPKNMBRVBMTLB-UHFFFAOYSA-N 2,3-dichloronaphthalene-1,4-dione Chemical compound C1=CC=C2C(=O)C(Cl)=C(Cl)C(=O)C2=C1 SVPKNMBRVBMTLB-UHFFFAOYSA-N 0.000 description 1
- BIECIOFZIILAAK-UHFFFAOYSA-N 2,3-diphenyl-5-(2-phenylethenyl)-1,3-dihydropyrazole Chemical compound N1N(C=2C=CC=CC=2)C(C=2C=CC=CC=2)C=C1C=CC1=CC=CC=C1 BIECIOFZIILAAK-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
- FKTICIGCPKISGI-UHFFFAOYSA-N 2,4-diphenyl-3h-benzo[f]cinnoline Chemical compound C12=CC=C3C=CC=CC3=C2C=C(C=2C=CC=CC=2)NN1C1=CC=CC=C1 FKTICIGCPKISGI-UHFFFAOYSA-N 0.000 description 1
- QAHMKHHCOXNIHO-UHFFFAOYSA-N 2,4-diphenylquinazoline Chemical compound C1=CC=CC=C1C1=NC(C=2C=CC=CC=2)=C(C=CC=C2)C2=N1 QAHMKHHCOXNIHO-UHFFFAOYSA-N 0.000 description 1
- FPQJIXBKABHGGB-UHFFFAOYSA-N 2,5-diphenyl-3-(2-phenylethenyl)-1,3-dihydropyrazole Chemical compound C1=C(C=2C=CC=CC=2)NN(C=2C=CC=CC=2)C1C=CC1=CC=CC=C1 FPQJIXBKABHGGB-UHFFFAOYSA-N 0.000 description 1
- KLJBWJNKXZYYHA-UHFFFAOYSA-N 2-(4-nitrophenyl)-2-(3-oxo-2-benzofuran-1-ylidene)acetonitrile Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(C#N)=C1C2=CC=CC=C2C(=O)O1 KLJBWJNKXZYYHA-UHFFFAOYSA-N 0.000 description 1
- ACTZPPLAFLLSAQ-UHFFFAOYSA-N 2-[nitro(phenyl)methylidene]propanedinitrile Chemical compound [N+](=O)([O-])C(C1=CC=CC=C1)=C(C#N)C#N ACTZPPLAFLLSAQ-UHFFFAOYSA-N 0.000 description 1
- FPKCTSIVDAWGFA-UHFFFAOYSA-N 2-chloroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3C(=O)C2=C1 FPKCTSIVDAWGFA-UHFFFAOYSA-N 0.000 description 1
- CMWKITSNTDAEDT-UHFFFAOYSA-N 2-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC=C1C=O CMWKITSNTDAEDT-UHFFFAOYSA-N 0.000 description 1
- OMXSHNIXAVHELO-UHFFFAOYSA-N 2-phenyl-4-(2-phenylethenyl)quinazoline Chemical compound C=1C=CC=CC=1C=CC(C1=CC=CC=C1N=1)=NC=1C1=CC=CC=C1 OMXSHNIXAVHELO-UHFFFAOYSA-N 0.000 description 1
- ZMESCNYFNZEIFB-UHFFFAOYSA-N 3-(4-methoxyphenyl)-5-[2-(4-methoxyphenyl)ethenyl]-2-phenyl-1,3-dihydropyrazole Chemical compound C1=CC(OC)=CC=C1C=CC1=CC(C=2C=CC(OC)=CC=2)N(C=2C=CC=CC=2)N1 ZMESCNYFNZEIFB-UHFFFAOYSA-N 0.000 description 1
- MRXCTUHFMJGHPM-UHFFFAOYSA-N 3-(furan-2-yl)-2,5-diphenyl-1,3-dihydropyrazole Chemical compound N1N(C=2C=CC=CC=2)C(C=2OC=CC=2)C=C1C1=CC=CC=C1 MRXCTUHFMJGHPM-UHFFFAOYSA-N 0.000 description 1
- JHKQSICMMKJIAA-UHFFFAOYSA-N 3h-1,3-benzothiazole-2-thione;lead Chemical compound [Pb].C1=CC=C2SC(=S)NC2=C1 JHKQSICMMKJIAA-UHFFFAOYSA-N 0.000 description 1
- OFQGIIIVIXXLRO-UHFFFAOYSA-N 3h-1,3-benzoxazole-2-thione;lead Chemical compound [Pb].C1=CC=C2OC(=S)NC2=C1 OFQGIIIVIXXLRO-UHFFFAOYSA-N 0.000 description 1
- UJEUBSWHCGDJQU-UHFFFAOYSA-N 4-chloro-1,8-naphthalic anhydride Chemical compound O=C1OC(=O)C2=CC=CC3=C2C1=CC=C3Cl UJEUBSWHCGDJQU-UHFFFAOYSA-N 0.000 description 1
- YXYUIABODWXVIK-UHFFFAOYSA-N 4-methyl-n,n-bis(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 YXYUIABODWXVIK-UHFFFAOYSA-N 0.000 description 1
- BXRFQSNOROATLV-UHFFFAOYSA-N 4-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(C=O)C=C1 BXRFQSNOROATLV-UHFFFAOYSA-N 0.000 description 1
- CMYMHIDTPBTIMX-UHFFFAOYSA-N 7-benzylquinolin-8-ol Chemical compound C1=CC2=CC=CN=C2C(O)=C1CC1=CC=CC=C1 CMYMHIDTPBTIMX-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- YYVYAPXYZVYDHN-UHFFFAOYSA-N 9,10-phenanthroquinone Chemical compound C1=CC=C2C(=O)C(=O)C3=CC=CC=C3C2=C1 YYVYAPXYZVYDHN-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-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
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 239000004727 Noryl Substances 0.000 description 1
- 229920001207 Noryl Polymers 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- JPBGLQJDCUZXEF-UHFFFAOYSA-N chromenylium Chemical class [O+]1=CC=CC2=CC=CC=C21 JPBGLQJDCUZXEF-UHFFFAOYSA-N 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
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 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
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000009477 glass transition Effects 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
- 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
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- XMSHLUJZPODALA-UHFFFAOYSA-N lead;5-methoxy-1,3-dihydrobenzimidazole-2-thione Chemical compound [Pb].COC1=CC=C2NC(=S)NC2=C1 XMSHLUJZPODALA-UHFFFAOYSA-N 0.000 description 1
- IJIZVJIJFGEFRG-UHFFFAOYSA-N lead;5-phenyl-3h-1,3-benzoxazole-2-thione Chemical compound [Pb].C=1C=C2OC(=S)NC2=CC=1C1=CC=CC=C1 IJIZVJIJFGEFRG-UHFFFAOYSA-N 0.000 description 1
- ONUVVJRBFDSALG-UHFFFAOYSA-N lead;quinolin-8-ol Chemical compound [Pb].C1=CN=C2C(O)=CC=CC2=C1 ONUVVJRBFDSALG-UHFFFAOYSA-N 0.000 description 1
- PRGAWFXXABCMIW-UHFFFAOYSA-L magnesium;quinolin-8-olate Chemical compound [Mg+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 PRGAWFXXABCMIW-UHFFFAOYSA-L 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- CXKWCBBOMKCUKX-UHFFFAOYSA-M methylene blue Chemical compound [Cl-].C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 CXKWCBBOMKCUKX-UHFFFAOYSA-M 0.000 description 1
- 229960000907 methylthioninium chloride Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- ISGXOWLMGOPVPB-UHFFFAOYSA-N n,n-dibenzylaniline Chemical compound C=1C=CC=CC=1CN(C=1C=CC=CC=1)CC1=CC=CC=C1 ISGXOWLMGOPVPB-UHFFFAOYSA-N 0.000 description 1
- VQVQWNNWJNMZFS-UHFFFAOYSA-N n,n-dimethyl-4-(2-phenylquinazolin-4-yl)aniline Chemical compound C1=CC(N(C)C)=CC=C1C1=NC(C=2C=CC=CC=2)=NC2=CC=CC=C12 VQVQWNNWJNMZFS-UHFFFAOYSA-N 0.000 description 1
- BDMYVUTVARPUCD-UHFFFAOYSA-N n-benzyl-n-naphthalen-2-ylnaphthalen-2-amine Chemical compound C=1C=C2C=CC=CC2=CC=1N(C=1C=C2C=CC=CC2=CC=1)CC1=CC=CC=C1 BDMYVUTVARPUCD-UHFFFAOYSA-N 0.000 description 1
- FKJARBPQBIATJT-UHFFFAOYSA-N n-benzyl-n-phenylaniline Chemical compound C=1C=CC=CC=1CN(C=1C=CC=CC=1)C1=CC=CC=C1 FKJARBPQBIATJT-UHFFFAOYSA-N 0.000 description 1
- VRUKENOGLFMZNY-UHFFFAOYSA-N n-cyclohexyl-n-phenylaniline Chemical compound C1CCCCC1N(C=1C=CC=CC=1)C1=CC=CC=C1 VRUKENOGLFMZNY-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000012188 paraffin wax 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
- 229920006287 phenoxy resin Polymers 0.000 description 1
- 239000013034 phenoxy resin Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229920002382 photo conductive polymer Polymers 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 125000005506 phthalide group Chemical group 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920013716 polyethylene resin Polymers 0.000 description 1
- 239000005518 polymer electrolyte Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical class C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 1
- 150000003246 quinazolines Chemical class 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 231100000812 repeated exposure Toxicity 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 150000003513 tertiary aromatic amines Chemical class 0.000 description 1
- 238000010998 test method Methods 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- PEQHIRFAKIASBK-UHFFFAOYSA-N tetraphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 PEQHIRFAKIASBK-UHFFFAOYSA-N 0.000 description 1
- 239000001016 thiazine dye Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- PGNWIWKMXVDXHP-UHFFFAOYSA-L zinc;1,3-benzothiazole-2-thiolate Chemical compound [Zn+2].C1=CC=C2SC([S-])=NC2=C1.C1=CC=C2SC([S-])=NC2=C1 PGNWIWKMXVDXHP-UHFFFAOYSA-L 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
- G03G5/05—Organic bonding materials; Methods for coating a substrate with a photoconductive layer; Inert supplements for use in photoconductive layers
- G03G5/0528—Macromolecular bonding materials
- G03G5/0557—Macromolecular bonding materials obtained otherwise than by reactions only involving carbon-to-carbon unsatured bonds
- G03G5/056—Polyesters
Landscapes
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Photoreceptors In Electrophotography (AREA)
- Polyesters Or Polycarbonates (AREA)
Description
本発明は電子写真用感光体に関するものであ
る。詳しくは有機系の光導電性物質を含有する感
光層を有する高感度の電子写真感光体に関するも
のである。
従来、電子写真用感光体の感光層にはセレン、
硫化カドミウム、酸化亜鉛等の無機系の光導電性
物質が広く用いられていた。近年、有機系の光導
電性物質を電子写真用感光体の感光層に用いる研
究が進み、そのいくつかが実用化されている。有
機系の光導電物質は無機系のものに比し、軽量で
ある、皮膜が容易である、感光体の製造が容易で
ある、種類によつては透明な感光体を製造できる
等の利点を有する。
有機系光導電性物質としてはポリビニルカルバ
ゾールをはじめとする光導電性ポリマーに関する
研究が多くなされてきたが、近年有機系の低分子
光導電性化合物が研究の中心となつてきた。この
原因としては低分子の光導電性化合物の中のいく
つかはポリビニルカルバゾール等よりもより高感
度な感光体を作る事が出来るということと、結合
剤樹脂として皮膜性、可とう性、接着性、といつ
た機械的特性の秀れたもの、更には高感度寄与
性、帯電保持性といつた電子写真特性の秀れたも
のを選択することにより、更に高感度で機械的な
特性に秀れた感光体が得やすくなつたことにほか
ならない。
そこで、本発明者は有機系の低分子光導電性化
合物を電子写真用感光体に用いる際に必要な結合
剤樹脂の重要性について認識を深め、鋭意研究し
たところ、従来の結合剤樹脂では考えられなかつ
た、高感度、及び高耐久性を有する電子写真用感
光体を提供する新規な結合剤樹脂を見出し本発明
に到つた。
すなわち、本発明の要旨とするところは一般式
で表わされるポリアリレート樹脂を少なくとも１
種を結合剤樹脂として含むことを特徴とする電子
写真用感光体に関する。
従来の低分子光導電性化合物に用いられる結合
剤樹脂としてはポリスチレン、スチレン−ブタジ
エン共重合体、ポリ酢酸ビニル、アクリル酸エス
テル、メタクリル酸エステル等のビニル系樹脂、
ポリビニルブチラール、ポリピニルアセタール、
ポリカーボネート、ポリエステル、ポリスルホ
ン、ポリフエニレンオキサイド、ポリウレタン、
セルローズエステル、フエノキシ樹脂、けい素樹
脂、エポキシ樹脂等がよく知られている。特にポ
リスチレン系樹脂、ポリカーボネート、ポリフエ
ニレンオキサイド（PPO）、ポリスルフオン樹
脂、ポリメチルメタクリレート及びノリル
（PPOとポリスチレンのブレンド）樹脂等は低分
子光導電性化合物の結合剤樹脂としては好まし
い。しかし更に電子写真特性の秀れた、又機械的
特性の秀れた電子写真用感光体を得るには不十分
な点があつた。このような点を改良する為に種々
の結合剤樹脂について検討した結果、本発明を完
成するに到つた。
本発明のポリアリレート樹脂はいわばポリカー
ボネート樹脂とポリエステル樹脂の中間的性質を
持つている樹脂といつてよく、強じんな皮膜形成
を有し、更に主鎖が剛直で例えばTg（ガラス転
移点）が200℃と高く、特に積層型電子写真用感
光体の電荷移動層中のバインダー樹脂として用い
る場合に不可欠の耐摩耗性、寸法安定性、耐熱
性、電荷保持性等に於ては従来からよく知られて
いる前述の結合剤樹脂を電荷移動層に用いた積層
型電子写真用感光体に比べて、すぐれた特性を発
揮する。
本発明の一般式で示されるポリアリレート樹脂
自体は、公知であり、例えばユニチカ(株)製、商品
名「Ｕ−ポリマー」として入手することができ
る。本発明のポリアリレート樹脂を単独で電子写
真用感光体の結合剤樹脂として用いても良いが、
他の樹脂を適当に加える事によつて更に高性能の
電子写真用感光体を得ることも出来る。これら樹
脂としては前述の樹脂の他、フエノール樹脂、ポ
リアミド樹脂、ポリエチレン樹脂、エポキシ樹脂
等の公知樹脂があげられるがポリアリレート樹脂
と一般に相溶性の良い樹脂がブレンド樹脂として
好ましい。これら樹脂のポリアリレート樹脂に対
する量は樹脂の種類によつて溶解性、相溶性等が
違い一概には言い難いが３割以下が好ましく、こ
れ以上加えるとポリアリレート樹脂の特徴が大き
く減じられる。又機械的強度を更に改善する目的
で可塑剤を添加することができる。可塑剤の例と
しては塩素化パラフイン、塩素化ビフエニール、
フタレート系可塑剤、フオスフエート系可塑剤等
が使用できる。
本発明の電子写真用感光体は前記一般式で表わ
されるポリアリレート樹脂を少なくとも１種結合
剤樹脂として含有する感光層を有する。種々の形
態の感光層が周知であるが、本発明の電子写真用
感光体の感光層はそのいずれであつてもよい。通
常、次に例示するタイプの感光層である。
(1) 光導電体物質と増感剤（化学増感剤、色素
等）をポリアリレート樹脂中に分散させた感光
層（単一層型感光体）
(2) 光導電体物質をポリアリレート樹脂中に分散
させこれを電荷移動層とした感光層（積層型感
光体）
(3) 電荷発生体物質をポリアリレート樹脂中に分
散させこれを電荷発生層とした感光層（積層型
感光体）
本発明においてはポリアリレート樹脂を(2)のタ
イプの積層型感光体に用いた場合に、とくに高感
度で残留電位が少なく、初期電位が大きく、更に
感光層表面の耐摩耗性が強く、かつ寸法安定性に
特に秀れている点、この感光層を繰り返し使用し
た場合の転写画像のくずれ、画像濃度低下、感度
低下といつた現象の少ない耐久性にすぐれた画像
転写用感光体を得ることができる。
塗布液調製用の溶剤としては、テトラヒドロフ
ラン、１・４−ジオキサン等のエーテル類：メチ
ルエチルケトン、シクロヘキサノン等のケトン
類：トルエン、キシレン等の芳香族炭化水素：
Ｎ・Ｎ−ジメチルホルムアミド、アセトニトリ
ル、Ｎ−メチルピロリドン、ジメチルスルホキシ
ド等の非プロトン性極性溶剤：酢酸エチル、メチ
ルセルソルブアセテート等のエステル類：ジクロ
ルエタン、クロロホルム等の塩素化水素モノクロ
ルベンゼン等の塩素化芳香族炭化水素などの溶剤
があげられるが、特に塩素化炭化水素、１・４−
ジオキサン等がポリアリレート樹脂の溶解性は良
かつた。
前記感光層に添加される光導電性物質、電荷発
生物質、染料色素、化学増感剤、としてはいずれ
も周知のものが使用できる。光を吸収すると極め
て高い効率で電荷キヤリヤーを発生する電荷発生
物質としては、セレン、セレンーテルル合金、セ
レンヒ素合金、硫化カドミウム等の無機化合物、
銅フタロシアニン、ペリレン系顔料、チオインジ
ゴ、キメクリドン、アントラキノン系顔料、ビス
アゾ系顔料、シアニン系顔料等の無機化合物が挙
げられる。染料としては、例えばメチルバイオレ
ツト、プリリアントグリーン、クリスタルバイオ
レツト等のトリフエニルメタン染料、メチレンブ
ルーなどのチアジン染料、キニザリン等のキノン
染料およびシアニン染料やピリリウム塩、チアピ
リリウム塩、ベンゾピリリウム塩等が挙げられ
る。
又、光導電性物質としては、前述のセレン、セ
レン−テルル合金、セレン−ヒ素合金、硫化カド
ミウムのほか、有機化合物として、
() 芳香族第３級アミノ化合物：
トリフエニルアミン、ジベンジルアニリン、
ジフエニルベンジルアミン、ジ−（Ｐ−クロロ
ベンジル）アニリン、ジ−（β−ナフチル）ベ
ンジルアミン、トリ−（Ｐ−トリル）アミン、
ジフエニルシクロヘキシルアミン等。
() 芳香族第３級ジアミノ化合物：
Ｎ・Ｎ・N′・N′−テトラベンジル−Ｐ−フ
エニレンジアミン、Ｎ・Ｎ・N′・N′−テトラ
（Ｐ−クロロベンジル）−Ｐ−フエニレンジアミ
ン、Ｎ・Ｎ・N′・N′−テトラメチル−Ｐ−フ
エニレンジアミン、Ｎ・Ｎ・N′・N′−テトラ
ベンジル−ｍ−フエニレンジアミン、Ｎ・Ｎ・
N′・N′−テトラメチルベンジジン、Ｎ・Ｎ・
N′・N′−テトラベンジルベンジジン、Ｎ・
Ｎ・N′・N′−テトラフエニル−ｐ−フエニレ
ンジアミン、Ｎ・Ｎ・N′・N′−テトラフエニ
ル−ｍ−フエニレンジアミン、１・１−ビス−
（４−Ｎ・Ｎ−ジベンジルアミンフエニル）−エ
タン、１・１−ビス−（４−Ｎ・Ｎ−ジベンジ
ルアミノフエニル）−プロパン、１・１−ビス
−（４−Ｎ・Ｎ−ジベンジルアミノフエニル）−
ブタン、１・１−ビス−（４−Ｎ・Ｎ−ジベン
ジルアミノフエニル）−２−メチルプロパン、
２・２−ビス−（４−Ｎ・Ｎ−ジベンジルアミ
ノフエニル）プロパン、２・２−ビス−（４−
Ｎ・Ｎ−ジベンジルアミノフエニル）−ブタ
ン、１・１−ビス〔４−Ｎ・Ｎ−ジ−（ｍ−メ
チルベンジルアミノフエニル）−プロパン、ビ
ス−（４−Ｎ・Ｎ−ジベンジルアミノフエニ
ル）−メタン、ビス−〔４−Ｎ・Ｎ−ジ−Ｐ−ク
ロロベンジルアミノフエニル）〕メタン、ビス
（４−Ｎ・Ｎ−ジメチルアミノ−１・１・１−
トリフエニルエタン、4′・4′−ベンジリジン−
ビス（Ｎ・Ｎ−ジエチル−ｍ−トルイジン）
4′・4″−ビス（ジエチルアミノ）−２・６−ジ
クロロ−2′・2″−ジメチルトリフエニルメタ
ン、４・4″−ビス（ジエチルアミノ−２・2″−
ジメチル）ジフエニル−ナフチルメタン、4′・
4″−ビス（ジメチルアミノ）−２−クロロ−
2′・2″−ジメチルトリフエニルメタン、ビス
（４−ジエチルアミノ）−１・１・１−トリフエ
ニルエタン、５・５−ジフエニル−２・４−ペ
ンタジユニリデン−４・４−ビス（Ｎ・Ｎ−ジ
エチル−ｍ−トルイジン）（註：下記構造式）
３・３−ジフエニルアリリジイン−４・4′−
ビス（Ｎ・Ｎ−ジエチル−ｍ−トルイジン）
（註：下記構造式）
ビス−（４−Ｎ・Ｎ−ジベンジルアミノフエ
ニル）エーテル、ビス−（４−Ｎ・Ｎ−ジエチ
ルアミノフエニル）エーテル、ピス−（４−
Ｎ・Ｎ−ジベンジルアミノフエニル）チオエー
テル、２・２−ビス（ジ−Ｐ−トリルアミノフ
エニル）プロパン、４・4′−ビス（ジ−Ｐ−ト
リルアミノ）−１・１・１−トリフエニルエタ
ン、４・４−ビス（ジベンジルアミノフエニ
ル）テトラフエニルメタンなど。
() 芳香族第３級トリアミノ化合物：
４・4′・4″−トリス（ジエチルアミノフエニ
ル）メタン、４−ジエチルアミノ、4′・4″−ビ
ス（ジエチルアミノ）−2′・2″−ジメチル−ト
リフエニルメタン（註：下記構造式）など。
() ポリビニルカルバゾール化合物：
ポリビニルカルバゾール、ハロゲン置換ポリ
ビニルカルバゾール、ビニルカルバゾールとス
チレンの共重合体、ビニルアントラセン−ビニ
ルカルバゾールの共重合体など。
() 縮合生成物：
アルデヒドと芳香族アミンの縮合生成物、第
３級芳香族アミンと芳香族ハロゲン化物の反応
物、ポリ−Ｐ−フエニレン−１・３・４−オキ
サジアゾール、ホルムアルデヒドと縮合多還化
合物の反応物など。
() 金属含有化合物：
２−メルカプト−ベンゾチアゾール−鉛塩、
２−メルカプト−ベンゾチアゾール亜鉛塩、２
−メルカプト−ベンゾチアゾール−鋼塩、２−
メルカプト−ベンゾオキサゾール−鉛塩、２−
メルカプト−５−フエニルベンゾオキサゾール
−鉛塩、２−メルカプト−６−メトキシベンゾ
イミダゾール鉛塩、８−ヒドロキシ−キノリン
−マグネシウム塩、８−ヒドロキシ−キノリ
ン、アルミニウム塩、８−ヒドロキシ−キノリ
ン−鉛塩、７−ベンジル−８−ヒドロキシ−キ
ノリン鋼塩、２−ヒドロキシ−４−メチル−ア
ゾベンゼン−鋼塩、２−ヒドロキシ−ベンゾル
デミン−亜鉛塩（註：下記構造式）など。
() 複素環化合物：
１・３・５−トリフエニル−ピラゾリン、１
−フエニル−３−（Ｐ−ジメチルアミノスチリ
ル）−５−（Ｐ−ジメチルアミノフエニル）−ピ
ラゾリン、１・５−ジフエニル−３−スチリル
−ピラゾリン、１・３−ジフエニル−５−スチ
リル−ピラゾリン、１・３−ジフエニル−５−
（Ｐ−ジメチルアミノフエニル）−ピラゾリン、
１・３−ジフエニル−５−フリル−ピラゾリ
ン、等のピラゾリン誘導体、３−（4′−ジメチ
ルアミノフエニル）−５・６−ジ−（4″−メトキ
シフエニル）−１・２・４−トリアジン、３−
（4′−ジメチルアミノフエニル）−５・６−ジビ
リジル（2″）−１・２・４−トリアジン（註：
下記構造式）
３−（4′−ジメチルアミノフエニル）−５・６
−ジ−（４−メトキシフエニル）−１・２・４−
トリアジン、３−（4′−ジメチルアミノフエニ
ル）−５・６−ジ−（4″−メトキシフエニル）−
１・２・４−トリアジン等の１・２・４−トリ
アジン誘導体、２・４−ジフエニル−キナゾリ
ン、２−フエニル−４−（4′−トリル）−キナゾ
リン、２−フエニル−４−（4′−ジメチルアミ
ノフエニル）−キナゾリン（註：下記構造式）
２−フエニル−４−スチリル−キナゾリン、
２・４−ジフエニル−７・８−ベンゾキナゾリ
ン等のキナゾリン誘導体、６−ヒドロキシ−２
−フエニル−３−（Ｐ−ジメチルアミノフエニ
ル）−ベンゾフラン（註：下記構造式）
６−ヒドロキシ−２・３−ジ（Ｐ−メトキシ
フエニル）−ベンゾフラン、２・３・５・６−
テトラ−（Ｐ−メトキシフエニル）−フロ−
（３・２）−ベンゾフラン等のベンゾフラン誘導
体、２・５−ビス−〔4′−ジメチルアミノフエ
ニル−（1′）〕−１・３・４−オキサジアゾー
ル、２・５−ビス−〔4′−ジエチルアミノフエ
ニル−（1′）〕−１・３・４−オキサジアゾー
ル、２・５−ビス−〔4′−イソアミルアミノ−
フエニル−（1′）〕−１・３・４−オキサジアゾ
ール、２・５−ビス−〔4′−シクロ−ベンテル
アミノフエニル−（1′）〕−１・３・４−オキサ
ジアゾール、２・５−ビス−〔4′−エチルアミ
ノ−フエニル−（1′）〕−１・３・４−オキサジ
アゾール等のオキサジアゾール誘導体などがあ
る。
更にこれら光導電性有機化合物と電荷移動錯
体を形成する電子吸引性化合物としては、例え
ばクロラニル、２・３−ジクロル−１・４−ナ
フトキノン、２−メチルアントラキノン、１−
ニトロアントラキノン、１−クロロ−５−ニト
ロアントラキノン、２−クロロアントラキノ
ン、フエナントレンキノンの様なキノン類、４
−ニトロベンズアルデヒド、３−クロロ−４−
ニトロベンズアルデヒドなどのアルデヒド類、
９−ベンゾイルアントラセンインダンジオン、
３・５−ジニトロベンゾフエノン、２・４・７
−トリニトロフルオレノン、３・3′・５・5′−
テトラニトロベンゾフエノン等のケトン類、無
水フタル酸、４−クロロナフタル酸無水物等の
酸無水物、テレフタラルマロノニトリル、４−
ニトロベンザルマロノニトリル等のシアノ化合
物、３−ベンザルフタリド、３−（α−シアノ
−ｐ−ニトロベンザル）フタリド、３−（α−
シアノ−ｐ−ニトロベンザル）−４・５・６・
７−テトラクロロフタリド等のフタリド類等の
電子吸引性化合物があげられる。
次に感光層が形成される導電性支持体として
は周知の電子写真用感光体に採用されているも
のが、いずれも使用できる。具体的には例えば
アルミニウム、銅等の金属ドラム、シートある
いはこれらの金属箔のラミネート物、蒸着物が
挙げられる。更に、金属粉末、カーボンブラツ
ク、ヨウ化銅、高分子電解質等の導電性物質を
適当なバインダーとともに塗布して導電処理し
たプラスチツクフイルム、紙等が挙げられる。
以上本発明電子写真用感光体について詳細に説
明したが、特徴について簡単に要約すると次の通
りである。
感度が非常に高く、かぶりの原因となる残留
電位が小さい。
皮膜強度が強く、特に光導電性有機化合物の
析晶防止能が大きい。
暗所での帯電保持性が高く、高帯電性を有す
る。
繰り返し使用の感光体については〜のほか
耐摩耗性にすぐれ感光体の表面機械的劣化が
小さい。
寸法安定性にすぐれた感光体のひずみ、のび
といつた現象が少なく耐久性にすぐれている。
多数回使用を行なつても表面電位の低下、感
度の低下といつた現象が少なくすぐれた電子写
真能を長期にわたつて保持する。
次に本発明を実施例により更に具体的に説明す
るが、本発明はその要旨をこえない限り以下の実
施例に限定されるものではない。
実施例 １
１−フエニル−３−（ｐ−メトキシスチリル）−
５−（ｐ−メトキシフエニル）−ピラゾリン（mp
＝156〜157℃）（註：下記構造式）
５ｇとポリアリレート樹脂（ユニチカ製、商品名
Ｕ−ポリマー）６ｇをモノクロロベンゼン50mlに
溶解して塗布液を調製した。また比較用としてポ
リアリレート樹脂の代りにポリスチレン樹脂（三
菱モンサント製、商品名スタイロン683）及び、
ポリメチルメタクリレート樹脂（和光純薬製）
各々６ｇを結合剤樹脂として用いた塗布液を調製
した。
次に、100μの膜厚のポリエステルフイルムに
ラミネートした厚さ10μのアルミ箔上にセレンを
真空蒸着し、約0.3μの厚さの電荷発生層を形成
させた。この上に前記３種類の塗布液をフイルム
アプリケーターで塗布、乾燥し、12μの厚さの電
荷移動層を形成させた。このようにして３種類の
積層型電子写真用感光体が得られた。
この感光体につい感度すなわち半減露光量（Ｅ
1/2）を測定したところ、ポリアリレート樹脂を
用いた感光体は、５ lux′sexであるのに対して
ポリスチレン樹脂を用いた感光体は８ lux′sec
であり、又ポリメチルメタクリレート樹脂を用い
た感光体は10 lux′secであつた。ここでいう半減
露光量とは、まず感光体を暗所で6KVのコロナ放
電により帯電させ、次いで白色光で露光し、表
面電位が初期表面電位の半分に減衰するのに要す
る露光量を測定することより求めた。
実施例 ２
実施例１で得た電子写真用感光体の耐久性テス
トを静電複写紙試験装置（川口電機製作所製モデ
ルSP−428）を用いて行なつた。ダイナミツク方
式で感光体サンプルを保持したターンテーブルを
約1000r.p.m.の回転しつつ、6.0KVののコロナ
放電を３秒間、300 luxの照度の白色光の露光を
５秒間行ない、このサイクルを繰り返し、一定回
数毎にスタテイク方式で感度の測定を行なつた。
繰り返しテスト前の感度は6KVののコロナ放
電、５ luxの照度の白色光露光のＥ1/2、V0帯
電、露光の繰り返し2000回後のＥ1/2、V0につい
て測定すると下記の通りであつた。ここでV0は
初期表面電位（Volt）である。
The present invention relates to a photoreceptor for electrophotography. Specifically, the present invention relates to a highly sensitive electrophotographic photoreceptor having a photosensitive layer containing an organic photoconductive substance. Conventionally, the photosensitive layer of electrophotographic photoreceptors contains selenium,
Inorganic photoconductive materials such as cadmium sulfide and zinc oxide were widely used. In recent years, research on the use of organic photoconductive substances in the photosensitive layer of electrophotographic photoreceptors has progressed, and some of them have been put into practical use. Organic photoconductive materials have advantages over inorganic materials, such as being lighter, easier to form a film, easier to manufacture photoreceptors, and depending on the type, transparent photoreceptors can be manufactured. have Many studies have been conducted on photoconductive polymers such as polyvinylcarbazole as organic photoconductive substances, but in recent years, research has focused on organic low-molecular photoconductive compounds. The reason for this is that some of the low-molecular photoconductive compounds can make photoreceptors with higher sensitivity than polyvinylcarbazole, etc., and that they have excellent film properties, flexibility, and adhesive properties as binder resins. By selecting a material with excellent mechanical properties such as , and furthermore, a material with excellent electrophotographic properties such as high sensitivity contribution and charge retention, it is possible to achieve even higher sensitivity and excellent mechanical properties. This simply means that it has become easier to obtain photoreceptors. Therefore, the present inventors have deepened their awareness of the importance of binder resins necessary when using organic low-molecular-weight photoconductive compounds in electrophotographic photoreceptors, and have conducted extensive research. The inventors have discovered a new binder resin that provides an electrophotographic photoreceptor with high sensitivity and high durability, which has not been achieved previously, and have arrived at the present invention. In other words, the gist of the present invention is the general formula At least 1 polyarylate resin represented by
The present invention relates to an electrophotographic photoreceptor characterized in that it contains a species as a binder resin. Examples of binder resins used in conventional low-molecular photoconductive compounds include vinyl resins such as polystyrene, styrene-butadiene copolymers, polyvinyl acetate, acrylic esters, and methacrylic esters;
polyvinyl butyral, polypynylacetal,
Polycarbonate, polyester, polysulfone, polyphenylene oxide, polyurethane,
Cellulose ester, phenoxy resin, silicone resin, epoxy resin, etc. are well known. In particular, polystyrene resins, polycarbonates, polyphenylene oxide (PPO), polysulfone resins, polymethyl methacrylate, and noryl (a blend of PPO and polystyrene) resins are preferred as binder resins for low-molecular photoconductive compounds. However, there were still problems in that it was insufficient to obtain an electrophotographic photoreceptor with excellent electrophotographic properties and mechanical properties. In order to improve these points, various binder resins were studied and the present invention was completed. The polyarylate resin of the present invention can be said to have intermediate properties between polycarbonate resin and polyester resin, and it forms a strong film, has a rigid main chain, and has a low Tg (glass transition point). It has been well known for its abrasion resistance, dimensional stability, heat resistance, charge retention properties, etc., which are as high as 200℃ and are essential when used as a binder resin in the charge transfer layer of a laminated electrophotographic photoreceptor. It exhibits superior characteristics compared to the laminated electrophotographic photoreceptor using the above-mentioned binder resin in the charge transfer layer. The polyarylate resin itself represented by the general formula of the present invention is publicly known and can be obtained, for example, from Unitika Co., Ltd. under the trade name "U-Polymer". Although the polyarylate resin of the present invention may be used alone as a binder resin for an electrophotographic photoreceptor,
By appropriately adding other resins, it is also possible to obtain electrophotographic photoreceptors with even higher performance. In addition to the above-mentioned resins, these resins include known resins such as phenol resins, polyamide resins, polyethylene resins, and epoxy resins, but resins that are generally compatible with polyarylate resins are preferred as blend resins. The amount of these resins relative to the polyarylate resin varies depending on the type of resin, such as solubility and compatibility, but it is difficult to generalize, but it is preferably 30% or less; if more than this is added, the characteristics of the polyarylate resin will be greatly reduced. Furthermore, a plasticizer can be added for the purpose of further improving mechanical strength. Examples of plasticizers include chlorinated paraffin, chlorinated biphenyl,
Phthalate plasticizers, phosphate plasticizers, etc. can be used. The electrophotographic photoreceptor of the present invention has a photosensitive layer containing at least one polyarylate resin represented by the above general formula as a binder resin. Various forms of photosensitive layers are well known, and the photosensitive layer of the electrophotographic photoreceptor of the present invention may be any of them. Usually, the photosensitive layer is of the type exemplified below. (1) A photosensitive layer in which a photoconductor material and a sensitizer (chemical sensitizer, dye, etc.) are dispersed in a polyarylate resin (single layer photoconductor) (2) A photoconductor material is dispersed in a polyarylate resin (3) Photosensitive layer (laminated photoreceptor) in which a charge generating substance is dispersed in a polyarylate resin and used as a charge transfer layer (laminated photoreceptor) When polyarylate resin is used in the laminated photoreceptor of type (2), it exhibits particularly high sensitivity, low residual potential, large initial potential, strong abrasion resistance on the surface of the photosensitive layer, and dimensional stability. It is possible to obtain a photoreceptor for image transfer that has excellent durability and is less likely to cause distortion of the transferred image, decrease in image density, and decrease in sensitivity when this photosensitive layer is used repeatedly. . Solvents for preparing the coating solution include: ethers such as tetrahydrofuran and 1,4-dioxane; ketones such as methyl ethyl ketone and cyclohexanone; aromatic hydrocarbons such as toluene and xylene;
Aprotic polar solvents such as N/N-dimethylformamide, acetonitrile, N-methylpyrrolidone, and dimethyl sulfoxide; Esters such as ethyl acetate and methylcellosolve acetate; Chlorination of hydrogen chlorides such as dichloroethane and chloroform; monochlorobenzene, etc. Examples include solvents such as aromatic hydrocarbons, especially chlorinated hydrocarbons, 1,4-
Dioxane and the like had good solubility in polyarylate resin. Known photoconductive substances, charge generating substances, dyes, and chemical sensitizers can be used to add to the photosensitive layer. Charge-generating substances that generate charge carriers with extremely high efficiency when absorbing light include inorganic compounds such as selenium, selenium-tellurium alloys, selenium-arsenic alloys, and cadmium sulfide;
Examples include inorganic compounds such as copper phthalocyanine, perylene pigments, thioindigo, chimecridone, anthraquinone pigments, bisazo pigments, and cyanine pigments. Examples of dyes include triphenylmethane dyes such as methyl violet, priliant green, and crystal violet, thiazine dyes such as methylene blue, quinone dyes such as quinizarin, cyanine dyes, pyrylium salts, thiapyrylium salts, benzopyrylium salts, etc. Can be mentioned. In addition to the above-mentioned selenium, selenium-tellurium alloy, selenium-arsenic alloy, and cadmium sulfide as photoconductive substances, organic compounds such as () aromatic tertiary amino compounds: triphenylamine, dibenzylaniline,
Diphenylbenzylamine, di-(P-chlorobenzyl)aniline, di-(β-naphthyl)benzylamine, tri-(P-tolyl)amine,
Diphenylcyclohexylamine etc. () Aromatic tertiary diamino compounds: N・N・N′・N′-tetrabenzyl-P-phenylenediamine, N・N・N′・N′-tetra(P-chlorobenzyl)-P-phenylenediamine Nylenediamine, N・N・N′・N′-tetramethyl-P-phenylenediamine, N・N・N′・N′-tetrabenzyl-m-phenylenediamine, N・N・
N′・N′-tetramethylbenzidine, N・N・
N′・N′-tetrabenzylbenzidine, N・
N・N′・N′-tetraphenyl-p-phenylenediamine, N・N・N′・N′-tetraphenyl-m-phenylenediamine, 1,1-bis-
(4-N・N-dibenzylamine phenyl)-ethane, 1,1-bis-(4-N・N-dibenzylaminophenyl)-propane, 1,1-bis-(4-N・N -dibenzylaminophenyl)-
Butane, 1.1-bis-(4-N.N-dibenzylaminophenyl)-2-methylpropane,
2,2-bis-(4-N・N-dibenzylaminophenyl)propane, 2,2-bis-(4-
N・N-dibenzylaminophenyl)-butane, 1,1-bis[4-N・N-di-(m-methylbenzylaminophenyl)-propane, bis-(4-N・N-dibenzyl) aminophenyl)-methane, bis-[4-N.N-di-P-chlorobenzylaminophenyl)]methane, bis(4-N.N-dimethylamino-1.1.1-
Triphenylethane, 4′・4′-benzylidine-
Bis(N・N-diethyl-m-toluidine)
4′,4″-bis(diethylamino)-2,6-dichloro-2′,2″-dimethyltriphenylmethane, 4,4″-bis(diethylamino-2,2″-
dimethyl) diphenyl-naphthylmethane, 4′.
4″-bis(dimethylamino)-2-chloro-
2',2''-dimethyltriphenylmethane, bis(4-diethylamino)-1,1,1-triphenylethane, 5,5-diphenyl-2,4-pentadiunilidene-4,4-bis(N・N-diethyl-m-toluidine) (Note: Structural formula below) 3,3-diphenylallylidiin-4,4'-
Bis(N・N-diethyl-m-toluidine)
(Note: Structural formula below) Bis-(4-N・N-dibenzylaminophenyl) ether, Bis-(4-N・N-diethylaminophenyl) ether, Pis-(4-
N/N-dibenzylaminophenyl) thioether, 2,2-bis(di-P-tolylaminophenyl)propane, 4,4'-bis(di-P-tolylamino)-1,1,1-trif enylethane, 4,4-bis(dibenzylaminophenyl)tetraphenylmethane, etc. () Aromatic tertiary triamino compounds: 4,4',4''-tris(diethylaminophenyl)methane, 4-diethylamino, 4',4''-bis(diethylamino)-2',2''-dimethyl-trif enylmethane (note: structural formula below), etc. () Polyvinylcarbazole compounds: polyvinylcarbazole, halogen-substituted polyvinylcarbazole, copolymers of vinylcarbazole and styrene, copolymers of vinylanthracene-vinylcarbazole, etc. () Condensation product: Condensation product of aldehyde and aromatic amine, reaction product of tertiary aromatic amine and aromatic halide, poly-P-phenylene-1,3,4-oxadiazole, condensation with formaldehyde Reactants of polycyclic compounds, etc. () Metal-containing compound: 2-mercapto-benzothiazole-lead salt,
2-mercapto-benzothiazole zinc salt, 2
-mercapto-benzothiazole-steel salt, 2-
Mercapto-benzoxazole-lead salt, 2-
Mercapto-5-phenylbenzoxazole-lead salt, 2-mercapto-6-methoxybenzimidazole lead salt, 8-hydroxy-quinoline-magnesium salt, 8-hydroxy-quinoline, aluminum salt, 8-hydroxy-quinoline-lead salt , 7-benzyl-8-hydroxy-quinoline steel salt, 2-hydroxy-4-methyl-azobenzene-steel salt, 2-hydroxy-benzorudemine-zinc salt (note: the following structural formula), and the like. () Heterocyclic compound: 1,3,5-triphenyl-pyrazoline, 1
-phenyl-3-(P-dimethylaminophenyl)-5-(P-dimethylaminophenyl)-pyrazoline, 1,5-diphenyl-3-styryl-pyrazoline, 1,3-diphenyl-5-styryl-pyrazoline, 1,3-diphenyl-5-
(P-dimethylaminophenyl)-pyrazoline,
Pyrazoline derivatives such as 1,3-diphenyl-5-furyl-pyrazoline, 3-(4′-dimethylaminophenyl)-5,6-di-(4″-methoxyphenyl)-1,2,4- Triazine, 3-
(4′-dimethylaminophenyl)-5,6-diviridyl(2″)-1,2,4-triazine (Note:
Structural formula below) 3-(4'-dimethylaminophenyl)-5/6
-di-(4-methoxyphenyl)-1,2,4-
Triazine, 3-(4′-dimethylaminophenyl)-5,6-di-(4″-methoxyphenyl)-
1,2,4-triazine derivatives such as 1,2,4-triazine, 2,4-diphenyl-quinazoline, 2-phenyl-4-(4'-tolyl)-quinazoline, 2-phenyl-4-(4' -dimethylaminophenyl)-quinazoline (Note: Structural formula below) 2-phenyl-4-styryl-quinazoline,
Quinazoline derivatives such as 2,4-diphenyl-7,8-benzoquinazoline, 6-hydroxy-2
-Phenyl-3-(P-dimethylaminophenyl)-benzofuran (Note: Structural formula below) 6-hydroxy-2,3-di(P-methoxyphenyl)-benzofuran, 2,3,5,6-
Tetra-(P-methoxyphenyl)-furo-
(3,2)-benzofuran derivatives such as benzofuran, 2,5-bis-[4'-dimethylaminophenyl-(1')]-1,3,4-oxadiazole, 2,5-bis-[ 4'-diethylaminophenyl-(1')]-1,3,4-oxadiazole, 2,5-bis-[4'-isoamylamino-
Phenyl-(1')]-1,3,4-oxadiazole, 2,5-bis-[4'-cyclo-bentelaminophenyl-(1')]-1,3,4-oxadiazole Examples thereof include azole and oxadiazole derivatives such as 2,5-bis-[4'-ethylamino-phenyl-(1')]-1,3,4-oxadiazole. Furthermore, examples of electron-withdrawing compounds that form charge transfer complexes with these photoconductive organic compounds include chloranil, 2,3-dichloro-1,4-naphthoquinone, 2-methylanthraquinone, 1-
Quinones such as nitroanthraquinone, 1-chloro-5-nitroanthraquinone, 2-chloroanthraquinone, phenanthrenequinone, 4
-Nitrobenzaldehyde, 3-chloro-4-
aldehydes such as nitrobenzaldehyde,
9-benzoylanthracene indanedione,
3,5-dinitrobenzophenone, 2,4,7
-Trinitrofluorenone, 3, 3', 5, 5'-
Ketones such as tetranitrobenzophenone, acid anhydrides such as phthalic anhydride and 4-chloronaphthalic anhydride, terephthalalmalononitrile, 4-
Cyano compounds such as nitrobenzalmalononitrile, 3-benzalphthalide, 3-(α-cyano-p-nitrobenzal)phthalide, 3-(α-
cyano-p-nitrobenzal)-4, 5, 6,
Examples include electron-withdrawing compounds such as phthalides such as 7-tetrachlorophthalide. Next, as the conductive support on which the photosensitive layer is formed, any of those employed in well-known electrophotographic photoreceptors can be used. Specific examples include metal drums and sheets made of aluminum, copper, etc., and laminates and vapor deposits of these metal foils. Further examples include plastic film, paper, etc. which are coated with a conductive substance such as metal powder, carbon black, copper iodide, or polymer electrolyte together with a suitable binder to conductivity treatment. The electrophotographic photoreceptor of the present invention has been described above in detail, and its features can be briefly summarized as follows. The sensitivity is extremely high and the residual potential that causes fogging is small. The coating has strong strength, and is particularly effective in preventing crystallization of photoconductive organic compounds. It has high charge retention and high chargeability in the dark. Regarding photoconductors that are used repeatedly, in addition to ~, they have excellent abrasion resistance and minimal mechanical deterioration of the surface of the photoconductor. The photoreceptor has excellent dimensional stability, and has excellent durability with less distortion and spreading phenomena. Even after repeated use, there are few phenomena such as a decrease in surface potential or sensitivity, and excellent electrophotographic performance is maintained over a long period of time. Next, the present invention will be explained in more detail with reference to examples, but the present invention is not limited to the following examples unless it exceeds the gist thereof. Example 1 1-phenyl-3-(p-methoxystyryl)-
5-(p-methoxyphenyl)-pyrazoline (mp
=156~157℃) (Note: Structural formula below) A coating solution was prepared by dissolving 5 g of polyarylate resin and 6 g of polyarylate resin (manufactured by Unitika, trade name: U-Polymer) in 50 ml of monochlorobenzene. For comparison, polystyrene resin (manufactured by Mitsubishi Monsanto, trade name Styron 683) was used instead of polyarylate resin.
Polymethyl methacrylate resin (manufactured by Wako Pure Chemical Industries)
A coating solution was prepared using 6 g of each as a binder resin. Next, selenium was vacuum-deposited on a 10μ thick aluminum foil laminated to a 100μ thick polyester film to form a charge generation layer about 0.3μ thick. The three types of coating liquids described above were applied onto this using a film applicator and dried to form a charge transfer layer having a thickness of 12 μm. In this way, three types of laminated electrophotographic photoreceptors were obtained. The sensitivity of this photoreceptor, that is, the half-decreased exposure amount (E
1/2), the photoreceptor using polyarylate resin has a 5 lux'sex, while the photoreceptor using a polystyrene resin has a lux of 8 lux'sec.
and the photoreceptor using polymethyl methacrylate resin had a power of 10 lux'sec. The half-decreased exposure amount here means that the photoreceptor is first charged by 6KV corona discharge in a dark place, then exposed to white light, and the amount of exposure required for the surface potential to attenuate to half of the initial surface potential is measured. I asked for it more than anything. Example 2 A durability test of the electrophotographic photoreceptor obtained in Example 1 was conducted using an electrostatic copying paper tester (Model SP-428 manufactured by Kawaguchi Electric Seisakusho). While rotating the turntable holding the photoreceptor sample in a dynamic manner at approximately 1000 rpm, a corona discharge of 6.0 KV was applied for 3 seconds, and exposure to white light with an illuminance of 300 lux was performed for 5 seconds, and this cycle was repeated. Sensitivity was measured using the static method at regular intervals.
The sensitivity before repeated testing is as follows when measured for corona discharge of 6KV, E1/2, V 0 of white light exposure with illuminance of 5 lux, E1/2, V 0 after 2000 repeated exposures. Ta. Here, V 0 is the initial surface potential (Volt).
【表】
本実施例よりポリアリレート樹脂を電荷移動層
の結合剤樹脂として使用した感光体は多数回の繰
り返しに対しても電子写真特性の変動のきわめて
少ない感光体であることがわかるであろう。
実施例 ３
実施例１で得た感光体を電子写真複写機（小西
六写真工業社製、商標UBix−800）にセツトし
て、原稿の複写を行なつたところ、ポリアリレー
ト樹脂を用いた感光体はコピー枚数が5000枚目の
所でも１枚目とかわらない、かぶりのない鮮明な
画像が得られた。これに対してポリスチレン樹脂
を用いた感光体は100枚目ぐらいから画像のとび
及び画像濃度低下が起つた。又ポリメチルメタク
リレート樹脂を用いた感光体は画像のゆがみ、濃
度低下といつた現象が20〜30枚目から起つた。
次に塗料によく用いられている落砂試験法によ
つて各感光体の摩耗性について調べて見ると下記
の表となる。[Table] From this example, it can be seen that the photoreceptor using polyarylate resin as the binder resin in the charge transfer layer shows extremely little variation in electrophotographic characteristics even after repeated use. . Example 3 The photoreceptor obtained in Example 1 was set in an electrophotographic copying machine (manufactured by Konishiroku Photo Industry Co., Ltd., trade name: UBix-800) and an original was copied. Even after the 5,000th copy of the body, a clear image with no fogging was obtained, which was the same as the first copy. On the other hand, with the photoreceptor using polystyrene resin, image skipping and image density reduction occurred after about the 100th sheet. In addition, with the photoreceptor using polymethyl methacrylate resin, phenomena such as image distortion and decrease in density occurred from the 20th to 30th sheet. Next, the abrasion resistance of each photoreceptor was examined using a sand drop test method that is often used for paints, and the following table was obtained.
【表】
この表からわかる通りポリアリレートを用いた
感光体は摩耗しにくく、このことは多数複写の際
の感光体の表面皮膜が主として紙とのまさつに対
して強い抵抗性を有していることがわかる。
実施例 ４[Table] As can be seen from this table, photoreceptors using polyarylate are less likely to wear out. This means that the surface film of the photoreceptor has strong resistance to contact with paper during multiple copying. I know that there is. Example 4
【表】
からなる液をボールミル中で粉砕混合して電荷発
生顔料分散液を得る。この分散液をアルミニウム
蒸着したポリエステルフイルム上にフイルムアダ
プターで塗布、乾燥し厚さ１μの電荷発生層を形
成させた。この電荷発生層の上に
４・4′−ビス（ジエチルアミノ）−２・2′−ジ
メチル−トリフエニルメタン（mp＝109.5〜110
℃）（註：下記構造式）
５ｇとポリアリレート樹脂（ユニチカ製、商品名
Ｕ−ポリマー）６ｇをモノクロロベンゼン50mlに
溶解させた塗布液を塗布、乾燥して膜厚13μの電
荷移動層を積層した。
このようにして得た感光体のＥ1/2は３
lux′sec、V0は1200Volt、摩耗率は0.18熱変形温
度（感光体が熱によつて変形する最低温度）は
135℃であつた。またこの塗布液中に0.5ｇのポリ
メチルメタクリレート樹脂を加えて得た電荷発生
層を積層した感光体はＥ1/2、V0熱変形温度が変
わることなく、摩耗率が0.12になり耐摩耗性の改
善が認められた。
実施例 ５
実施例１で用いたピラゾリン化合物10ｇ、下記
に示す各樹脂12ｇとＮ・N′−ジエチル−２−チ
オバルピツール酸0.6ｇ、クリスタルバイオレツ
ト0.05ｇを２塩化エタン100ｇに溶解し、導電処
理を促したコート紙上にスキージングドクトルで
乾燥後の膜厚が６μになる様に塗布乾燥して、感
光層を形成させ電子写真用感光体を得た。この感
光体を暗所で6KVの及びのコロナ放電で帯電
し、Ｅ1/2及びV0を測定した所それぞれ下記の通
りであつた。[Table] A charge-generating pigment dispersion is obtained by pulverizing and mixing the liquid in a ball mill. This dispersion was applied onto a polyester film coated with aluminum using a film adapter and dried to form a charge generating layer having a thickness of 1 μm. On this charge generation layer, 4,4'-bis(diethylamino)-2,2'-dimethyl-triphenylmethane (mp = 109.5 to 110
°C) (Note: Structural formula below) A coating solution prepared by dissolving 5 g of polyarylate resin and 6 g of polyarylate resin (manufactured by Unitika, trade name U-Polymer) in 50 ml of monochlorobenzene was applied and dried to form a charge transfer layer with a thickness of 13 μm. The E1/2 of the photoreceptor obtained in this way is 3
lux′sec, V 0 is 1200 Volt, wear rate is 0.18, and thermal deformation temperature (minimum temperature at which the photoreceptor deforms due to heat) is
It was 135℃. In addition, the photoconductor laminated with a charge generation layer obtained by adding 0.5 g of polymethyl methacrylate resin to this coating solution has a wear resistance of 0.12 without changing the E1/2, V0 heat distortion temperature. Improvement was observed. Example 5 10 g of the pyrazoline compound used in Example 1, 12 g of each resin shown below, 0.6 g of N.N'-diethyl-2-thiobalpituric acid, and 0.05 g of crystal violet were dissolved in 100 g of ethane dichloride and subjected to conductive treatment. The photosensitive layer was formed by coating and drying on coated paper using a squeegee doctor so that the film thickness after drying was 6 μm, thereby obtaining a photoreceptor for electrophotography. This photoreceptor was charged with a corona discharge of 6 KV in a dark place, and E1/2 and V0 were measured as shown below.
【表】【table】
【表】
この表より光導電性有機化合物の代表的結合剤
樹脂の中でポリアリレート樹脂を用いた感光体は
帯電、帯電のいずれにおいても最も秀れた感
度を示すことが明らかになつた。[Table] From this table, it is clear that among typical binder resins for photoconductive organic compounds, the photoreceptor using polyarylate resin exhibits the best sensitivity in both charging and charging.
Claims (1)
ポリアリレート樹脂を少なくとも１種を結合剤樹
脂として含むことを特徴とする電子写真用感光
体。 ２ 導電性支持体上に光を吸収して電荷担体を発
生する薄膜電荷発生層とその上に電荷の保持と発
生した電荷担体を移動させる電荷移動層とを組み
合せてなる複合型電子写真感光体の該電荷移動層
中に、一般式で表わされるポリアレート樹脂を少
なくとも１種を結合剤樹脂として含む特許請求の
範囲第１項記載の電子写真用感光体。[Scope of Claims] 1. An electrophotographic photoreceptor comprising at least one polyarylate resin represented by the following general formula as a binder resin on a conductive support. 2. A composite electrophotographic photoreceptor comprising a thin charge generation layer on a conductive support that absorbs light and generates charge carriers, and a charge transfer layer thereon that retains charges and moves the generated charge carriers. 2. The electrophotographic photoreceptor according to claim 1, wherein said charge transfer layer contains at least one polyarylate resin represented by the general formula as a binder resin.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3854380A JPS56135844A (en) | 1980-03-26 | 1980-03-26 | Electrophotographic receptor |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3854380A JPS56135844A (en) | 1980-03-26 | 1980-03-26 | Electrophotographic receptor |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS56135844A JPS56135844A (en) | 1981-10-23 |
| JPS6155672B2 true JPS6155672B2 (en) | 1986-11-28 |
Family
ID=12528194
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3854380A Granted JPS56135844A (en) | 1980-03-26 | 1980-03-26 | Electrophotographic receptor |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS56135844A (en) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5730841A (en) * | 1980-07-31 | 1982-02-19 | Fuji Xerox Co Ltd | Electrophotographic receptor |
| JPS5774748A (en) * | 1980-10-28 | 1982-05-11 | Canon Inc | Image retaining member |
| JPS5962860A (en) * | 1982-10-04 | 1984-04-10 | Mitsubishi Paper Mills Ltd | Improved laminate type electrophotographic receptor |
| JPS59168451A (en) * | 1983-03-15 | 1984-09-22 | Mitsubishi Paper Mills Ltd | Electrophotographic sensitive body |
| JPH02132453A (en) * | 1988-11-14 | 1990-05-21 | Konica Corp | Electrophotographic sensitive body |
| JP2729741B2 (en) * | 1993-03-11 | 1998-03-18 | 富士ゼロックス株式会社 | Electrophotographic photoreceptor |
| EP1286224A1 (en) | 2001-08-21 | 2003-02-26 | Mitsubishi Chemical Corporation | Electrophotographic photoreceptor |
| JP2003162157A (en) * | 2001-08-31 | 2003-06-06 | Canon Inc | Process cartridge, electrophotographic device and intermediate transfer belt |
| JP4214866B2 (en) | 2003-08-28 | 2009-01-28 | 三菱化学株式会社 | Electrophotographic photoreceptor |
| CN100474127C (en) | 2003-09-02 | 2009-04-01 | 三菱化学株式会社 | Electrophotographic photoreceptor |
| JP4336559B2 (en) | 2003-10-08 | 2009-09-30 | 富士電機デバイステクノロジー株式会社 | Electrophotographic photoreceptor and method for producing the same |
| DE602005026946D1 (en) | 2004-07-16 | 2011-04-28 | Mitsubishi Chem Corp | ELECTRO-PHOTOGRAPHIC LIGHT-SENSITIVE BODY |
| JP4642447B2 (en) | 2004-08-27 | 2011-03-02 | 株式会社リコー | Aromatic polyester resin and electrophotographic photoreceptor using the same |
| US8273509B2 (en) | 2006-01-06 | 2012-09-25 | Mitsubishi Chemical Corporation | Electrophotographic photoreceptor, and image forming device and electrophotographic photoreceptor cartridge using the same member cartridge |
| WO2007135983A1 (en) | 2006-05-18 | 2007-11-29 | Mitsubishi Chemical Corporation | Electrophotographic photosensitive body, image forming device, and electrophotographic cartridge |
| JP5493708B2 (en) * | 2009-10-28 | 2014-05-14 | 三菱化学株式会社 | Electrophotographic photosensitive member, electrophotographic cartridge, and image forming apparatus |
| WO2015005442A1 (en) | 2013-07-12 | 2015-01-15 | 三菱化学株式会社 | Electrophotographic photoreceptor, electrophotographic photoreceptor cartridge, image formation device, and polyarylate resin |
| JP6729157B2 (en) | 2016-08-10 | 2020-07-22 | 京セラドキュメントソリューションズ株式会社 | Electrophotographic photoreceptor, process cartridge, and image forming apparatus |
| JP6565824B2 (en) | 2016-08-10 | 2019-08-28 | 京セラドキュメントソリューションズ株式会社 | Electrophotographic photosensitive member, process cartridge, and image forming apparatus |
| US10761439B2 (en) | 2016-08-10 | 2020-09-01 | Kyocera Document Solutions Inc. | Polyarylate resin and electrophotographic photosensitive member |
| WO2018123425A1 (en) | 2016-12-26 | 2018-07-05 | 京セラドキュメントソリューションズ株式会社 | Electrophotographic photosensitive body, process cartridge, and image formation device |
| JP6642735B2 (en) | 2016-12-26 | 2020-02-12 | 京セラドキュメントソリューションズ株式会社 | Electrophotographic photosensitive member, process cartridge, and image forming apparatus |
| CN110431489B (en) | 2017-04-28 | 2023-04-21 | 京瓷办公信息***株式会社 | Electrophotographic photoreceptor, process cartridge, and image forming apparatus |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5057440A (en) * | 1973-09-19 | 1975-05-19 | ||
| JPS5188226A (en) * | 1974-12-20 | 1976-08-02 | ||
| JPS5226228A (en) * | 1975-08-22 | 1977-02-26 | Mitsubishi Electric Corp | Electrophotographic light sensitive plate |
-
1980
- 1980-03-26 JP JP3854380A patent/JPS56135844A/en active Granted
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5057440A (en) * | 1973-09-19 | 1975-05-19 | ||
| JPS5188226A (en) * | 1974-12-20 | 1976-08-02 | ||
| JPS5226228A (en) * | 1975-08-22 | 1977-02-26 | Mitsubishi Electric Corp | Electrophotographic light sensitive plate |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS56135844A (en) | 1981-10-23 |
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