JPH0567232B2 - - Google Patents
Info
- Publication number
- JPH0567232B2 JPH0567232B2 JP61243699A JP24369986A JPH0567232B2 JP H0567232 B2 JPH0567232 B2 JP H0567232B2 JP 61243699 A JP61243699 A JP 61243699A JP 24369986 A JP24369986 A JP 24369986A JP H0567232 B2 JPH0567232 B2 JP H0567232B2
- Authority
- JP
- Japan
- Prior art keywords
- layer
- photoreceptor
- charge
- derivatives
- pigments
- 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
- 239000010410 layer Substances 0.000 claims description 61
- 108091008695 photoreceptors Proteins 0.000 claims description 58
- 150000001875 compounds Chemical class 0.000 claims description 30
- 239000000126 substance Substances 0.000 claims description 29
- 239000011241 protective layer Substances 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000000049 pigment Substances 0.000 description 30
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 20
- -1 bisazo compound Chemical class 0.000 description 12
- 230000035945 sensitivity Effects 0.000 description 10
- 239000000463 material Substances 0.000 description 9
- 239000002344 surface layer Substances 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 6
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 5
- 230000006870 function Effects 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 4
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 230000006866 deterioration Effects 0.000 description 4
- 229920001296 polysiloxane Polymers 0.000 description 4
- 229910052711 selenium Inorganic materials 0.000 description 4
- 239000011669 selenium Substances 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
- 239000004419 Panlite Substances 0.000 description 3
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 3
- 239000004431 polycarbonate resin Substances 0.000 description 3
- 229920005668 polycarbonate resin Polymers 0.000 description 3
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 2
- WUPHOULIZUERAE-UHFFFAOYSA-N 3-(oxolan-2-yl)propanoic acid Chemical compound OC(=O)CCC1CCCO1 WUPHOULIZUERAE-UHFFFAOYSA-N 0.000 description 2
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 206010034972 Photosensitivity reaction Diseases 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- 229910052980 cadmium sulfide Inorganic materials 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 125000006575 electron-withdrawing group Chemical group 0.000 description 2
- 239000011888 foil Substances 0.000 description 2
- 239000001023 inorganic pigment Substances 0.000 description 2
- BSIHWSXXPBAGTC-UHFFFAOYSA-N isoviolanthrone Chemical class C12=CC=CC=C2C(=O)C2=CC=C3C(C4=C56)=CC=C5C5=CC=CC=C5C(=O)C6=CC=C4C4=C3C2=C1C=C4 BSIHWSXXPBAGTC-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000012860 organic pigment Substances 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 230000036211 photosensitivity Effects 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 229920006267 polyester film Polymers 0.000 description 2
- 150000003219 pyrazolines Chemical class 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical class S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 2
- SJHPCNCNNSSLPL-CSKARUKUSA-N (4e)-4-(ethoxymethylidene)-2-phenyl-1,3-oxazol-5-one Chemical class O1C(=O)C(=C/OCC)\N=C1C1=CC=CC=C1 SJHPCNCNNSSLPL-CSKARUKUSA-N 0.000 description 1
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- ZXBSSAFKXWFUMF-UHFFFAOYSA-N 1,2,3-trinitrofluoren-9-one Chemical compound C12=CC=CC=C2C(=O)C2=C1C=C([N+](=O)[O-])C([N+]([O-])=O)=C2[N+]([O-])=O ZXBSSAFKXWFUMF-UHFFFAOYSA-N 0.000 description 1
- WPMHMYHJGDAHKX-UHFFFAOYSA-N 1-ethenylpyrene Chemical compound C1=C2C(C=C)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 WPMHMYHJGDAHKX-UHFFFAOYSA-N 0.000 description 1
- BIEFDNUEROKZRA-UHFFFAOYSA-N 2-(2-phenylethenyl)aniline Chemical class NC1=CC=CC=C1C=CC1=CC=CC=C1 BIEFDNUEROKZRA-UHFFFAOYSA-N 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 1
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 description 1
- OGOYZCQQQFAGRI-UHFFFAOYSA-N 9-ethenylanthracene Chemical compound C1=CC=C2C(C=C)=C(C=CC=C3)C3=CC2=C1 OGOYZCQQQFAGRI-UHFFFAOYSA-N 0.000 description 1
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 1
- 229910000967 As alloy Inorganic materials 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241001561902 Chaetodon citrinellus Species 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- WZELXJBMMZFDDU-UHFFFAOYSA-N Imidazol-2-one Chemical class O=C1N=CC=N1 WZELXJBMMZFDDU-UHFFFAOYSA-N 0.000 description 1
- 235000000177 Indigofera tinctoria Nutrition 0.000 description 1
- 229930192627 Naphthoquinone Natural products 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 241000519995 Stachys sylvatica Species 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- 229910001215 Te alloy Inorganic materials 0.000 description 1
- ZTWQZJLUUZHJGS-UHFFFAOYSA-N Vat Yellow 4 Chemical class C12=CC=CC=C2C(=O)C2=CC=C3C4=CC=CC=C4C(=O)C4=C3C2=C1C=C4 ZTWQZJLUUZHJGS-UHFFFAOYSA-N 0.000 description 1
- QLNFINLXAKOTJB-UHFFFAOYSA-N [As].[Se] Chemical compound [As].[Se] QLNFINLXAKOTJB-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 150000001251 acridines 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
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- PGEHNUUBUQTUJB-UHFFFAOYSA-N anthanthrone Chemical class C1=CC=C2C(=O)C3=CC=C4C=CC=C5C(=O)C6=CC=C1C2=C6C3=C54 PGEHNUUBUQTUJB-UHFFFAOYSA-N 0.000 description 1
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 1
- 229940027998 antiseptic and disinfectant acridine derivative Drugs 0.000 description 1
- 150000001556 benzimidazoles Chemical class 0.000 description 1
- XJHABGPPCLHLLV-UHFFFAOYSA-N benzo[de]isoquinoline-1,3-dione Chemical compound C1=CC(C(=O)NC2=O)=C3C2=CC=CC3=C1 XJHABGPPCLHLLV-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- UHYPYGJEEGLRJD-UHFFFAOYSA-N cadmium(2+);selenium(2-) Chemical compound [Se-2].[Cd+2] UHYPYGJEEGLRJD-UHFFFAOYSA-N 0.000 description 1
- JLATXDOZXBEBJX-UHFFFAOYSA-N cadmium(2+);selenium(2-);sulfide Chemical compound [S-2].[Se-2].[Cd+2].[Cd+2] JLATXDOZXBEBJX-UHFFFAOYSA-N 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000005626 carbonium group Chemical group 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000005496 eutectics Effects 0.000 description 1
- 230000005294 ferromagnetic effect Effects 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 230000001771 impaired effect Effects 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
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 229910000464 lead oxide Inorganic materials 0.000 description 1
- 229910052981 lead sulfide Inorganic materials 0.000 description 1
- 229940056932 lead sulfide Drugs 0.000 description 1
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 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
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 description 1
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 150000007978 oxazole derivatives Chemical class 0.000 description 1
- YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical compound C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 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
- 125000001791 phenazinyl group Chemical class C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- INAAIJLSXJJHOZ-UHFFFAOYSA-N pibenzimol Chemical class 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
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 150000004060 quinone imines Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- QXKXDIKCIPXUPL-UHFFFAOYSA-N sulfanylidenemercury Chemical compound [Hg]=S QXKXDIKCIPXUPL-UHFFFAOYSA-N 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 150000007979 thiazole derivatives Chemical class 0.000 description 1
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 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
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- YKSGNOMLAIJTLT-UHFFFAOYSA-N violanthrone Chemical class C12=C3C4=CC=C2C2=CC=CC=C2C(=O)C1=CC=C3C1=CC=C2C(=O)C3=CC=CC=C3C3=CC=C4C1=C32 YKSGNOMLAIJTLT-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/05—Organic bonding materials; Methods for coating a substrate with a photoconductive layer; Inert supplements for use in photoconductive layers
- G03G5/0503—Inert supplements
- G03G5/051—Organic non-macromolecular compounds
- G03G5/0517—Organic non-macromolecular compounds comprising one or more cyclic groups consisting of carbon-atoms only
-
- 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
- G03G5/14—Inert intermediate or cover layers for charge-receiving layers
- G03G5/147—Cover layers
- G03G5/14708—Cover layers comprising organic material
Description
〔産業上の利用分野〕
本発明は電子写真感光体に関し、特に正帯電用
感光体に関する。
〔従来の技術〕
従来、例えば電子写真感光体としては、セレ
ン、酸化亜鉛、硫化カドミウム等の無機光導電性
物質を含有する感光層を有する感光体が広く用い
られている。
一方、種々の有機光導電性物質を電子写真感光
体の感光層の材料として利用することが近年活発
に開発、研究されている。
例えば特公昭50−10496号公報には、ポリ−Ｎ
−ビニルカルバゾールと２，４，７，−トリニト
ロ−９−フルオレノンを含有した感光層を有する
有機感光体について記載されている。しかしこの
感光体は、感度及び耐久性において必ずしも満足
できるものではない。このような欠点を改善する
ために、感光層において、電荷発生機能と電荷輸
送機能とを異なる物質に個別に分担させることに
より、感度が高くて耐久性の大きい有機感光体を
開発する試みがなされている。
このような、いわば機能分離型の電子写真感光
体においては、各機能を発揮する物質を広い範囲
のものから選択することができるので、任意の特
性を有する電子写真感光体を比較的容易に作製す
ることが可能である。
こうした機能分離型の電子写真感光体に有効な
電荷発生物質として、従来数多くの物質が提案さ
れている。無機物質を用いる例としては、例えば
特公昭43−16198号公報に記載されているように、
無定形セレンがあり、これは有機電荷輸送物質と
組み合わせる。
また、有機染料や有機顔料を電荷発生物質とし
て用いた電子写真感光体も多数提案されており、
例えば、ビスアゾ化合物を含有する感光層を有す
るものは、特開昭47−37543号、同55−22834号、
同54−79632号、同56−116040号各公報等により
既に知られている。
ところで、前記有機光導電性物質を用いた従来
の感光体は通常、負帯電用として使用されてい
る。
この理由は、負帯電使用の場合には、電荷のう
ちホールの移動度が大きいことから、光感度等の
面で有利なためである。しかしながら、このよう
な負帯電使用では、次の如き問題があることが判
明している。即ち、帯電器による負帯電時に雰囲
気中にオゾンが発生し易くなり、環境条件を悪く
するという問題がある。さらに他の問題は、負帯
電用感光体の現像には正極性のトナーが必要とな
るが、正極性のトナーは強磁性体電荷粒子に対す
る摩擦帯電系列からみて製造が困難であることで
ある。
そこで、有機光導電性物質を用いる感光体を正
帯電で使用することが提案されている。
例えば、電荷発生層上に電荷輸送層を積層して
感光体を形成する際、感光体表面の正電荷を能率
よく打消すため前記電荷輸送層に電子輸送性能の
大きい、例えばトリニトロフルオレノンを使用し
ているが、該物質は発ガン性があり、公害上極め
て不適当である。
さらに正帯電用感光体として、米国特許第
3615414号明細書には、チアピリリウム塩（電荷
発生物質）をポリカーボネート（バインダー樹
脂）と共晶錯体を形成するように含有させたもの
が示されている。しかしこの公知の感光体では、
メモリー現象が大きく、ゴーストも発生し易いと
いう欠点がある。又米国特許第3357989号明細書
にも、フタロシアニンを含有せしめた感光体が示
されているが、フタロシアニンは結晶型によつて
特性が変化する上に、結晶型を厳密に制御しなけ
ればならないという弊害があり、かつメモリー現
象が大きく、短波長感度が低いため前記短波長を
含む可視光を光源とする複写機には不適当なもの
とされる。
このように正帯電用感光体を得るための試みが
種々行なわれているが、いずれも光感度、メモリ
ー又は公害等の点で改善すべき多くの問題点があ
る。
そこで光照射時ホール及び電子を発生する電荷
発生物質を含有する電荷発生層を上層（表面層）
とし、ホール輸送機能を有する電荷輸送物質を含
む電荷輸送層を下層とする積層構成の感光層を有
する感光体を正帯電用として使用することが考え
られる。
さらに又、前記電荷発生物質と前記電荷輸送物
質を含む単層構成の感光層を有する感光体も正帯
電用として使用可能と考えられる。なおかかる正
帯電用とされる感光体においては、構造中に例え
ば電子吸引性基を有する電荷発生物質を用いるよ
うにすれば、感光体表面の正電荷を打消すための
電子の移動が早くなり、高感度特性が得られるこ
とが考えられる。
しかしながら、前記正帯電用感光体はいずれも
電荷発生物質を含む層が表面層として形成される
ため、光照射、コロナ放電、湿度、特に機械的摩
擦等の外部作用に敏感な電荷発生物質が前記表面
層近傍に存在することとなり、感光体の保存中及
び像形成の過程で電子写真性能が劣化し、画質が
低下するようになる。
従来の電荷輸送層を表面層とする負帯電用感光
体においては、前記各種の各部作用の影響は極め
て少なく、むしろ前記電荷輸送層が下層の電荷発
生層を保護する作用を有している。
これに反して正帯電用感光体の場合は表面層と
される電荷発生物質を含む層が外部作用、特に現
像及びクリーニング等により機械的摩耗及び損傷
をうけ、白ポチ、白筋等の画像欠陥その他表面電
位、感度、メモリー、残留電位等の電子写真性能
の劣化が生ずるようになる。
そこで、例えば絶縁性かつ透明な樹脂から成る
薄い保護層を設け、前記電荷発生物質を含む層を
補強することが考えられるが、光照射時発生する
電荷が該保護層でブロツキングされて光導電性が
失なわれるという問題がある。
また、表面層となる電荷発生層の膜厚を増すこ
とにより電荷発生層の耐摩耗性および耐傷性を高
めることが考えられるが、膜厚の増加が感度低下
を招くという問題がある。
〔発明の目的〕
従つて本発明の目的は、有機光導電性物質を用
いて正帯電用として好適に構成され、耐傷性に優
れ高感度で耐久性があり、しかもオゾン酸化耐性
にも勝る電子写真感光体を提供することにある。
〔発明の構成および作用効果〕
本発明の目的は、導電性支持体上に電荷輸送
層、電荷発生層および必要に応じて保護層を順次
積層した電子写真感光体において、電荷発生層中
に電荷輸送物質を含有し、かつ電荷発生層中ある
いは保護層中に下記一般式で示される化合物を含
有する正帯電用電子写真感光体によつて達成され
る。
一般式
[Industrial Application Field] The present invention relates to an electrophotographic photoreceptor, and particularly to a positively charging photoreceptor. [Prior Art] Conventionally, for example, as an electrophotographic photoreceptor, a photoreceptor having a photosensitive layer containing an inorganic photoconductive substance such as selenium, zinc oxide, or cadmium sulfide has been widely used. On the other hand, the use of various organic photoconductive substances as materials for photosensitive layers of electrophotographic photoreceptors has been actively developed and researched in recent years. For example, in Japanese Patent Publication No. 50-10496, poly-N
- describes an organic photoreceptor having a photosensitive layer containing vinylcarbazole and 2,4,7,-trinitro-9-fluorenone. However, this photoreceptor is not necessarily satisfactory in sensitivity and durability. In order to improve these drawbacks, attempts have been made to develop organic photoreceptors with high sensitivity and durability by assigning the charge generation function and charge transport function to different substances in the photosensitive layer. ing. In such so-called function-separated type electrophotographic photoreceptors, it is possible to select substances that exhibit each function from a wide range of materials, so it is relatively easy to produce electrophotographic photoreceptors with arbitrary characteristics. It is possible to do so. Many substances have been proposed as charge-generating substances that are effective for such functionally separated electrophotographic photoreceptors. Examples of using inorganic substances include, for example, as described in Japanese Patent Publication No. 16198/1983,
There is amorphous selenium, which is combined with organic charge transport materials. In addition, many electrophotographic photoreceptors using organic dyes or organic pigments as charge-generating substances have been proposed.
For example, those having a photosensitive layer containing a bisazo compound are disclosed in JP-A-47-37543, JP-A-55-22834,
This is already known from Publications No. 54-79632 and No. 56-116040. By the way, the conventional photoreceptor using the organic photoconductive substance is usually used for negative charging. The reason for this is that when negative charging is used, the mobility of holes among the charges is large, which is advantageous in terms of photosensitivity and the like. However, it has been found that using such negative charging causes the following problems. That is, there is a problem in that ozone is likely to be generated in the atmosphere during negative charging by the charger, worsening the environmental conditions. Still another problem is that positive polarity toner is required for development of negatively charged photoreceptors, but positive polarity toner is difficult to manufacture in view of the triboelectric charging sequence with respect to ferromagnetic charged particles. Therefore, it has been proposed to use a positively charged photoreceptor using an organic photoconductive substance. For example, when forming a photoreceptor by laminating a charge transport layer on a charge generation layer, a material with high electron transport performance, such as trinitrofluorenone, is used in the charge transport layer to efficiently cancel the positive charge on the surface of the photoreceptor. However, the substance is carcinogenic and is extremely unsuitable from a pollution standpoint. Furthermore, as a positive charging photoreceptor, the U.S. Patent No.
No. 3,615,414 discloses a material containing a thiapyrylium salt (charge generating substance) so as to form a eutectic complex with polycarbonate (binder resin). However, with this known photoreceptor,
The disadvantage is that the memory phenomenon is large and ghosts are likely to occur. U.S. Patent No. 3,357,989 also discloses a photoreceptor containing phthalocyanine, but the characteristics of phthalocyanine change depending on the crystal type, and the crystal type must be strictly controlled. It has disadvantages, has a large memory phenomenon, and has low short wavelength sensitivity, making it unsuitable for copying machines that use visible light including the short wavelengths as a light source. As described above, various attempts have been made to obtain photoreceptors for positive charging, but all of them have many problems that need to be improved in terms of photosensitivity, memory, pollution, etc. Therefore, a charge generation layer containing a charge generation substance that generates holes and electrons when irradiated with light is added as an upper layer (surface layer).
It is conceivable that a photoreceptor having a photosensitive layer having a laminated structure with a charge transporting layer containing a charge transporting substance having a hole transporting function as a lower layer may be used for positive charging. Furthermore, it is considered that a photoreceptor having a single-layered photosensitive layer containing the charge generating substance and the charge transporting substance can also be used for positive charging. In addition, in such a photoreceptor that is used for positive charging, if a charge generating substance having, for example, an electron-withdrawing group is used in the structure, the movement of electrons to cancel the positive charge on the surface of the photoreceptor will be accelerated. , it is thought that high sensitivity characteristics can be obtained. However, since all of the positive charging photoreceptors have a layer containing a charge-generating substance formed as a surface layer, the charge-generating substance is sensitive to external effects such as light irradiation, corona discharge, humidity, and especially mechanical friction. Since they are present near the surface layer, electrophotographic performance deteriorates during storage of the photoreceptor and during image formation, leading to a decrease in image quality. In a negative charging photoreceptor having a conventional charge transport layer as a surface layer, the effects of the various functions described above are extremely small; rather, the charge transport layer has the effect of protecting the underlying charge generation layer. On the other hand, in the case of a positively charging photoreceptor, the surface layer containing a charge-generating substance is subject to mechanical abrasion and damage due to external effects, especially development and cleaning, resulting in image defects such as white spots and white streaks. Other electrophotographic performance such as surface potential, sensitivity, memory, and residual potential deteriorates. Therefore, it is conceivable to provide a thin protective layer made of an insulating and transparent resin to reinforce the layer containing the charge-generating substance, but the protective layer blocks the charges generated during light irradiation, resulting in photoconductivity. The problem is that the information is lost. Further, it is possible to improve the wear resistance and scratch resistance of the charge generation layer by increasing the thickness of the charge generation layer serving as the surface layer, but there is a problem that the increase in the thickness causes a decrease in sensitivity. [Object of the Invention] Accordingly, the object of the present invention is to provide an electronic photoconductor that is suitably configured for positive charging using an organic photoconductive substance, has excellent scratch resistance, high sensitivity, and durability, and has excellent ozone oxidation resistance. The purpose of the present invention is to provide a photographic photoreceptor. [Structure and Effects of the Invention] An object of the present invention is to provide an electrophotographic photoreceptor in which a charge transport layer, a charge generation layer, and, if necessary, a protective layer are sequentially laminated on a conductive support. This is achieved by a positively charging electrophotographic photoreceptor containing a transport substance and a compound represented by the following general formula in the charge generation layer or protective layer. general formula
【化】
式中、R1は、水素原子、ヒドロキシル基また
はアルコキシ基を表し、R2およびR3は各々、水
素原子またはアルキル基を表す。ただしR2およ
びR3が同時に水素原子であることはない。
なお、電荷発生層の膜厚が２〜7μｍである場
合に本発明の効果がより発揮される。
従来の技術でも記述したように有機光導電性物
質を用いた正帯電用感光体においては、電荷発生
層（以下、CGLと略すことがある）が表面層と
なるので耐傷性に欠け、耐久性向上のためには
CGL膜厚を厚くする必要がある。しかしながら、
膜厚を厚くすると感度低下を引き起こす。この感
度低下を抑制する手段としてCGL中への電荷輸
送物質（以下、CTMと略すことがある）添加が
あるが、このCTMは電荷発生物質（以下、CGM
と略すことがある）に比べオゾン酸化を受け易い
構造を有するので、オゾンにより容易に劣化され
感光体の耐久性が損われてしまう。
本発明者らは、オゾン劣化性の改良に関し鋭意
検討の結果、正帯電用感光体の表面層である
CGL中に本発明の化合物を含有させることによ
り、上記劣化を著しく軽減できることを見い出し
本発明をなすに至つた。
作用効果の詳細は不明であるが、オゾンが
CGL中のCTMを劣化するより前に本発明の化合
物に作用し、それ以上のオゾン酸化をガードする
ことによりCTMが保護されるものと考える。
本発明の化合物は自身の酸化によつてCTMの
オゾン劣化を防止するので、必要に応じてCGL
上に保護層（以下、OCLと略すことがある）を
設けた感光体においては、勿論OCL中に添加さ
れるが、CGLにも添加されてもよく、更にCTM
を主成分とする電荷輸送層（以下、CTLと略す
ことがある）にも添加されてよい。
以下、本発明をより具体的に詳述する。
前記一般式で示される本発明の化合物は、アミ
ノ基がアルキル基で置換されたアニリン、ｐ−ア
ミノフエノールまたはｐ−アルコキシアニリン誘
導体である。
一般式において、R1で表されるアルコキシ基
は炭素数１〜18のアルコキシ基が好ましく、具体
的にメトキシ基、エトキシ基、ヘキシルオキシ
基、デシロキシ基、ドデシルオキシ基等を挙げる
ことができる。R2およびR3で表されるアルキル
基は直鎖でも分岐でもよく、好ましくは炭素数１
〜18のアルキル基で、具体的にメチル基、エチル
基、ｉ−プロピル基、ｉ−ブチル基、２−メチル
ブチル基、オクチル基、デシル基、ドデシル基、
ペンタデシル基等を挙げることができる。
本発明に好ましく用いられる化合物の代表的具
体例を以下に示すが、これに限定されるものでは
ない。embedded image In the formula, R 1 represents a hydrogen atom, a hydroxyl group or an alkoxy group, and R 2 and R 3 each represent a hydrogen atom or an alkyl group. However, R 2 and R 3 are never hydrogen atoms at the same time. Note that the effects of the present invention are more effectively exhibited when the thickness of the charge generation layer is 2 to 7 μm. As described in the conventional technology, positively charging photoreceptors using organic photoconductive substances lack scratch resistance and lack durability because the charge generation layer (hereinafter sometimes abbreviated as CGL) is the surface layer. In order to improve
It is necessary to increase the CGL film thickness. however,
Increasing the film thickness causes a decrease in sensitivity. One way to suppress this decrease in sensitivity is to add a charge transport material (hereinafter sometimes abbreviated as CTM) to CGL, but this CTM is a charge generating material (hereinafter referred to as CGM).
Since it has a structure that is more susceptible to ozone oxidation than the photoreceptor (sometimes abbreviated as ), it is easily deteriorated by ozone and the durability of the photoreceptor is impaired. As a result of intensive studies on improving ozone deterioration resistance, the present inventors discovered that the surface layer of a positive charging photoreceptor
The present inventors have discovered that the above deterioration can be significantly reduced by incorporating the compound of the present invention into CGL, leading to the present invention. Although the details of its effects are unknown, ozone
It is believed that the compound of the present invention acts on the compound of the present invention before CTM in CGL deteriorates and protects CTM by guarding against further ozone oxidation. Since the compound of the present invention prevents ozone deterioration of CTM by its own oxidation, CGL can be used as needed.
In photoreceptors with a protective layer (hereinafter sometimes abbreviated as OCL) on top, it is of course added to OCL, but it may also be added to CGL, and CTM
It may also be added to a charge transport layer (hereinafter sometimes abbreviated as CTL) whose main component is CTL. The present invention will be described in more detail below. The compound of the present invention represented by the above general formula is an aniline, p-aminophenol or p-alkoxyaniline derivative in which the amino group is substituted with an alkyl group. In the general formula, the alkoxy group represented by R 1 is preferably an alkoxy group having 1 to 18 carbon atoms, and specific examples include a methoxy group, an ethoxy group, a hexyloxy group, a desiloxy group, a dodecyloxy group, and the like. The alkyl group represented by R 2 and R 3 may be linear or branched, and preferably has 1 carbon number.
~18 alkyl groups, specifically methyl group, ethyl group, i-propyl group, i-butyl group, 2-methylbutyl group, octyl group, decyl group, dodecyl group,
Examples include pentadecyl group. Typical specific examples of compounds preferably used in the present invention are shown below, but the invention is not limited thereto.
【表】【table】
【表】
本発明の化合物の添加量は、CGL中に用いら
れる場合、CGL中のCTMに対して0.1〜100重量
％、好ましくは１〜50重量％、特に好ましくは５
〜25重量％である。また、OCL中に用いられる
場合、OCL中のバインダー樹脂に対して0.1〜100
重量％、好ましくは１〜50重量％である。
次に本発明の感光体の構成を図面によつて説明
する。感光体としては例えば第１図に示すように
支持体１（導電性支持体またはシート上に導電層
を設けたもの）上にCTMと必要に応じてバイン
ダー樹脂を含有する電荷輸送層２を下層とし、
CGM、CTMと必要に応じてバインダー樹脂を含
有する電荷発生層３を上層とする積層構成の感光
層４を設けたもの、第２図に示すように第１図の
感光層の上に保護層（OCL）４を設けたもの及
び第３図に示すように支持体上にCGMとCTMと
必要に応じてバインダー樹脂を含有する単層構成
の感光層４を設けたもの、等が挙げられるが、第
３図の単層構成の感光層上にOCLが設けられて
もよく、また支持体と感光層の間に中間層が設け
られてもよい。
次に本発明に適する電荷発生物質としては、可
視光を吸収してフリー電荷を発生するものであれ
ば、無機顔料及び有機色素の何れをも用いること
ができる。無定形セレン、三方晶系セレン、セレ
ン−砒素合金、セレン−テルル合金、硫化カドミ
ウム、セレン化カドミウム、硫セレン化カドミウ
ム、硫化水銀、酸化鉛、硫化鉛等の無機顔料の
外、次の代表例で示されるような有機顔料を用い
てもよい。
(1) モノアゾ顔料、ポリアゾ顔料、金属錯塩アゾ
顔料、ピラゾロンアゾ顔料、スチルベンアゾ及
びチアゾールアゾ顔料等のアゾ系顔料。
(2) ペリレン酸無水物及びペリレン酸イミド等の
ペリレン系顔料。
(3) アントラキノン誘導体、アントアントロン誘
導体、ジベンズピレンキノン誘導体、ピラント
ロン誘導体、ビオラントロン誘導体及びイソビ
オラントロン誘導体等のアントラキノン系又は
多環キノン系顔料
(4) インジゴ誘導体及びチオインジゴ誘導体等の
インジゴイド系顔料
(5) 金属フタロシアニン及び無金属フタロシアニ
ン等のフタロシアニン系顔料
(6) ジフエニルメタン系顔料、トリフエニルメタ
ン顔料、キサンテン顔料及びアクリジン顔料等
のカルボニウム系顔料
(7) アジン顔料、オキサジン顔料及びチアジン顔
料等のキノンイミン系顔料
(8) シアニン顔料及びアゾメチン顔料等のメチン
系顔料
(9) キノリン系顔料
(10) ニトロ系顔料
(11) ニトロソ系顔料
(12) ベンゾキノン及びナフトキノン系顔料
(13) ナフタルイミド系顔料
(14) ビスベンズイミダゾール誘導体等のペリノン
系顔料
電子吸引性基を有する種々のアゾ顔料が、感
度、メモリー現象、残留電位等の電子写真特性の
良好さから用いられるが耐オゾン性の点で多環キ
ノン系顔料が最も好ましい。
詳細は不明であるが、おそらくアゾ基はオゾン
酸化を受け易く電子写真特性が低下してしまう
が、多環キノン類はオゾンに対して不活性である
ためと思われる。
前記本発明に用いられるアゾ系顔料としては、
例えば次の例示化合物群〔〕〜〔〕で示され
るものがある。[Table] When used in CGL, the amount of the compound of the present invention added is 0.1 to 100% by weight, preferably 1 to 50% by weight, particularly preferably 5% by weight, based on CTM in CGL.
~25% by weight. In addition, when used in OCL, 0.1 to 100
% by weight, preferably from 1 to 50% by weight. Next, the structure of the photoreceptor of the present invention will be explained with reference to the drawings. For example, as shown in FIG. 1, the photoreceptor has a support 1 (a conductive support or a sheet with a conductive layer provided thereon) and a charge transport layer 2 containing CTM and, if necessary, a binder resin, as a lower layer. year,
A photosensitive layer 4 having a laminated structure consisting of CGM, CTM and a charge generating layer 3 containing a binder resin as an upper layer, as shown in FIG. 2, has a protective layer on top of the photosensitive layer shown in FIG. (OCL) 4, and as shown in FIG. 3, a single-layer photosensitive layer 4 containing CGM, CTM, and binder resin as necessary is provided on a support. , an OCL may be provided on the photosensitive layer having a single layer structure as shown in FIG. 3, or an intermediate layer may be provided between the support and the photosensitive layer. Next, as the charge generating substance suitable for the present invention, any of inorganic pigments and organic dyes can be used as long as it absorbs visible light and generates free charges. In addition to inorganic pigments such as amorphous selenium, trigonal selenium, selenium-arsenic alloy, selenium-tellurium alloy, cadmium sulfide, cadmium selenide, cadmium selenide sulfide, mercury sulfide, lead oxide, lead sulfide, the following representative examples Organic pigments such as those shown may also be used. (1) Azo pigments such as monoazo pigments, polyazo pigments, metal complex azo pigments, pyrazolone azo pigments, stilbene azo and thiazole azo pigments. (2) Perylene pigments such as perylene anhydride and perylene imide. (3) Anthraquinone or polycyclic quinone pigments such as anthraquinone derivatives, anthanthrone derivatives, dibenzpyrenequinone derivatives, pyrantrone derivatives, violanthrone derivatives, and isoviolanthrone derivatives (4) Indigoid pigments such as indigo derivatives and thioindigo derivatives (5) Phthalocyanine pigments such as metal phthalocyanine and metal-free phthalocyanine (6) Carbonium pigments such as diphenylmethane pigment, triphenylmethane pigment, xanthene pigment and acridine pigment (7) Quinone imine such as azine pigment, oxazine pigment and thiazine pigment Cyanine pigments and azomethine pigments (9) Quinoline pigments (10) Nitro pigments (11) Nitroso pigments (12) Benzoquinone and naphthoquinone pigments (13) Naphthalimide pigments (14) ) Perinone pigments such as bisbenzimidazole derivatives Various azo pigments with electron-withdrawing groups are used because of their good electrophotographic properties such as sensitivity, memory phenomenon, and residual potential, but polycyclic quinones are preferred due to their ozone resistance. pigments are most preferred. Although the details are unknown, this is probably because the azo group is susceptible to ozone oxidation and the electrophotographic properties deteriorate, whereas polycyclic quinones are inert to ozone. As the azo pigment used in the present invention,
For example, there are compounds shown in the following exemplified compound groups [] to [].
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】
また、以下の多環キノン顔料から成る例示化合
物群〔〕〜〔〕はCGMとして最も好ましく
使用できる。[Table] Furthermore, the following exemplified compound groups [] to [] consisting of polycyclic quinone pigments can be most preferably used as CGM.
【表】【table】
【表】【table】
【表】【table】
【表】
次に本発明で使用可能な電荷輸送物質として
は、特に制限はないが、例えばオキサゾール誘導
体、オキサジアゾール誘導体、チアゾール誘導
体、チアジアゾール誘導体、トリアゾール誘導
体、イミダゾール誘導体、イミダゾロン誘導体、
イミタゾリジン誘導体、ビスイミダゾリジン誘導
体、スチリル化合物、ヒドラゾン化合物、ピラゾ
リン誘導体、オキサゾロン誘導体、ベンジチアゾ
ール誘導体、ベンズイミダゾール誘導体、キナゾ
リン誘導体、ベンジフラン誘導体、アクリジン誘
導体、フエナジン誘導体、アミノスチルベン誘導
体、ポリ−Ｎ−ビニルカルバゾール、ポリ−１−
ビニルピレン、ポリ−９−ビニルアントラセン等
であつてよい。
しかしながら光照射時発生するホールの支持体
側への輸送能力が優れている外、前記キヤリア発
生物質との組合せに好適なものが好ましく用いら
れ、かかるCTMとしては、例えば下記例示化合
物群〔〕又は〔〕で示されるスチル化合物が
使用される。[Table] Next, there are no particular limitations on charge transport substances that can be used in the present invention, but examples include oxazole derivatives, oxadiazole derivatives, thiazole derivatives, thiadiazole derivatives, triazole derivatives, imidazole derivatives, imidazolone derivatives,
Imitazolidine derivatives, bisimidazolidine derivatives, styryl compounds, hydrazone compounds, pyrazoline derivatives, oxazolone derivatives, benzithiazole derivatives, benzimidazole derivatives, quinazoline derivatives, benzifuran derivatives, acridine derivatives, phenazine derivatives, aminostilbene derivatives, poly-N-vinylcarbazole , poly-1-
It may be vinylpyrene, poly-9-vinylanthracene, etc. However, it is preferable to use a CTM that has an excellent ability to transport holes generated during light irradiation to the support side and is suitable for combination with the carrier generating substance. Examples of such CTM include the following exemplified compound group [] or [ ] is used.
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】
また、CTMとして下記例示化合物群〔XI〕〜
〔〕で示されるヒドラゾン化合物も使用可能
である。[Table] In addition, the following exemplified compound groups [XI] ~
Hydrazone compounds represented by [ ] can also be used.
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】
また、CTMとして下記例示化合物〔〕で
示されるピラゾリン化合物も使用可能である。[Table] In addition, pyrazoline compounds shown in the following exemplified compounds [] can also be used as CTMs.
【表】【table】
【表】【table】
【表】
また、CTMとして下記例示化合物群〔〕
で示されるアミン誘導体も使用可能である。[Table] In addition, the following exemplified compound group as CTM []
Amine derivatives represented by can also be used.
【表】【table】
【表】【table】
【表】【table】
以下本発明を実施例により説明するが、これに
より本発明の実施の態様が限定されるものではな
い。
実施例 １
アルミニウム箔をラミネートしたポリエステル
フイルムより成る導電性支持体上に、塩化ビニル
−酢酸ビニル−無水マレイン酸共重合体（エスレ
ツクMF−10、積水化学工業社製）よりなる厚さ
0.1μｍの中間層を形成した。
次いでポリカーボネート樹脂（パンライトＬ−
1250、帝人化成社製）／CTM（−75）＝100／75
（重量比）を16.5重量％含有する１，２−ジクロ
ルエタン溶液を中間層上にデイツプ塗布し、15μ
ｍ厚の電荷輸送層を形成した。次に、CGMとし
て昇華した４，10−ジブロムアンスアンスロン
（−３〕／パンライトＬ−1250−１／２（重量
比）が９重量％になるように１，２−ジクロルエ
タン中ボールミルで24時間粉砕し、更に24時間分
散した液にCTM（−75）をパンライトＬ−1250
に対して75重量％およびCTMに対して0.5重量％
の例示化合物８を加えた。この溶液にモノクロル
ベンゼンを加えて１，２−ジクロルベンゼン／モ
ノクロルベンゼン＝７／３（体積比）になるよう
に調製した分散液を前記CTL上にスプレー塗布
し、乾燥して5μｍの電荷発生層を形成し、積層
構成の感光層を有する本発明に係る感光体を得
た。
比較例 １
実施例１において、例示化合物８を除いた以外
は実施例１と全く同様にして比較の感光体を得
た。
実施例 ２
実施例１において、例示化合物８に代えて例示
化合物１１を用いた以外は全く同様にして感光体
を得た。
実施例 ３
実施例１の例示化合物８を除いた感光層（比較
例１の感光体に同じ）上に、熱硬化製アクリル−
メラミン−エポキシ（１：１：１）樹脂1.55重量
部および例示化合物８0.155重量部をモノクロル
ベンゼン／１，１，２−トリクロルエタン混合溶
媒に溶解させた塗布液をスプレー塗布し、乾燥し
て1μｍ厚の保護層を有する感光体を得た。
実施例 ４
実施例１の例示化合物８を除いた感光層上に、
シリコンハードコート用プライマーPH91（東芝
シリコン社製）を0.1μｍとなるようにスプレー塗
布し、更にその上にシリコンハードコートトスガ
ード510（東芝シリコン社製）及び例示化合物８を
樹脂100重量部にたいして10重量部となるよう添
加した溶液をスプレー塗布し、乾燥して1μｍ厚
の保護層を形成し感光体を得た。
実施例 ５
アルミニウム箔をラミネートしたポリエステル
フイルムより成る導電性支持体上に、塩化ビニル
−酢酸ビニル−無水マレイン酸共重合体（エスレ
ツクMF−10、前出）よりなる厚さ約0.1μｍの中
間層を形成した。
次いでCTL用塗布液としてブチラール樹脂
（エスレツクBX−１、積水化学社製）８重量％
とCTM（−75）６重量％をメチルエチルケトン
に溶解して得られる塗布液を前記中間層上に塗
布・乾燥して10μｍ厚の電荷輸送層を形成した。
次いでCGM（−７）0.2ｇをペイントコンデシ
ヨナー（Paint Conditioner、Red Devil社製）
で30分粉砕し、これにポリカーボネート樹脂（パ
ンライトＬ−1250、前出）を１，２−ジクロルエ
タン／１，１，２−トリクロルエタン混合溶媒に
0.5重量％となるよう溶解させた溶液を8.3ｇ加え
て３分間分散し、次いでこれにポリカーボネート
樹脂、CTM（−75）および例示化合物８をそれ
ぞれ3.3重量％、2.6重量％および0.26重量％とな
るように１，２−ジクロルエタン／１，１，２−
トリクロルエタン混合溶媒に溶解して得られる溶
液19.1ｇを加えてさらに30分間分散した。かくし
て得られた分散液を前記CTL上にスプレー塗布
し、かつ乾燥して5μｍ厚の電荷発生層を形成し、
積層構成の感光層を有する感光体を得た。
比較例 ２
実施例５において例示化合物８を除いた以外は
実施例５と全く同様にして比較の感光体を得た。
実施例 ６
実施例５において、例示化合物８に代えて例示
化合物１１を用いた以外は全く同様にして感光体
を得た。
実施例 ７
実施例５の例示化合物８を除いた感光層（比較
例２の感光体に同じ）上に、実施例３と同様の例
示化合物８を含有する保護層を設置し、感光体を
得た。
実施例 ８
実施例５の例示化合物８を除いた感光層上に、
実施例４と同様の例示化合物８を含有する保護層
を設置し、感光体を得た。
上記のようにして得られた感光体試料を次に示
すオゾン疲労試験機により耐オゾン性を評価し
た。すなわち、静電試験機（川口電機製作所製
SP−428型）にオゾン発生器（日本オゾン株式会
社製０−１−２型）およびオゾンモニター（エバ
ラ実業株式会社製EG−2001型）を取り付けた装
置を用いた。オゾン濃度90ppmにおいて感光体を
装着し、＋6KVの電圧を印加して５秒間のコロナ
放電により感光層を帯電させた後５秒間放置（こ
の時の電位を初期電位V0とする）し、次いで感
光層表面の照度が14ルツクスとなる状態でタング
ステンランプよりの光を照射し、この操作を100
回くり返した。
100回照射後の電位をV1とする時、V1／V0×
100（％）で耐オゾン性を表した。Ｖ／V0は100回
反復後の電位低下の程度を示すものであり、数値
が大きい程好ましい。
The present invention will be explained below with reference to Examples, but the embodiments of the present invention are not limited thereby. Example 1 A conductive support made of polyester film laminated with aluminum foil was coated with a layer of vinyl chloride-vinyl acetate-maleic anhydride copolymer (Eslec MF-10, manufactured by Sekisui Chemical Co., Ltd.).
An intermediate layer of 0.1 μm was formed. Next, polycarbonate resin (Panlite L-
1250, manufactured by Teijin Chemicals)/CTM (-75) = 100/75
A 1,2-dichloroethane solution containing 16.5% by weight of
A charge transport layer having a thickness of m was formed. Next, in a ball mill in 1,2-dichloroethane, 24 CTM (-75) is added to Panlite L-1250 in the liquid that is crushed for 24 hours and then dispersed for 24 hours.
75% by weight for and 0.5% by weight for CTM
Exemplified Compound 8 was added. A dispersion prepared by adding monochlorobenzene to this solution so that the ratio of 1,2-dichlorobenzene/monochlorobenzene was 7/3 (volume ratio) was spray coated onto the CTL and dried to generate a 5 μm charge. A photoreceptor according to the present invention having a photosensitive layer having a laminated structure was obtained. Comparative Example 1 A comparative photoreceptor was obtained in exactly the same manner as in Example 1 except that Exemplary Compound 8 was omitted. Example 2 A photoreceptor was obtained in exactly the same manner as in Example 1 except that Exemplified Compound 11 was used in place of Exemplified Compound 8. Example 3 On the photosensitive layer (same as the photoreceptor of Comparative Example 1) except for Exemplified Compound 8 of Example 1, a thermosetting acrylic film was applied.
A coating solution prepared by dissolving 1.55 parts by weight of melamine-epoxy (1:1:1) resin and 80.155 parts by weight of the exemplified compound in a mixed solvent of monochlorobenzene/1,1,2-trichloroethane was spray applied and dried. A photoreceptor having a protective layer with a thickness of 1 μm was obtained. Example 4 On the photosensitive layer excluding Exemplified Compound 8 of Example 1,
Primer PH91 for silicone hard coat (manufactured by Toshiba Silicone Co., Ltd.) was spray applied to a thickness of 0.1 μm, and on top of that, silicone hard coat Tosguard 510 (manufactured by Toshiba Silicone Co., Ltd.) and Exemplary Compound 8 were applied at 10% by weight per 100 parts by weight of the resin. The solution added in the amount of parts by weight was spray coated and dried to form a protective layer with a thickness of 1 μm to obtain a photoreceptor. Example 5 An intermediate layer with a thickness of about 0.1 μm made of vinyl chloride-vinyl acetate-maleic anhydride copolymer (Eslec MF-10, supra) was formed on a conductive support made of polyester film laminated with aluminum foil. was formed. Next, 8% by weight of butyral resin (Eslec BX-1, manufactured by Sekisui Chemical Co., Ltd.) was used as a CTL coating liquid.
A coating solution obtained by dissolving 6 wt.
Next, apply 0.2 g of CGM (-7) to a paint conditioner (Paint Conditioner, manufactured by Red Devil).
Grind for 30 minutes, and add polycarbonate resin (Panlite L-1250, mentioned above) to this in a mixed solvent of 1,2-dichloroethane/1,1,2-trichloroethane.
Add 8.3g of a solution dissolved to give a concentration of 0.5% by weight and disperse for 3 minutes, then add polycarbonate resin, CTM (-75), and Exemplary Compound 8 to this solution to give a concentration of 3.3% by weight, 2.6% by weight, and 0.26% by weight, respectively. 1,2-dichloroethane/1,1,2-
19.1 g of a solution obtained by dissolving in a trichloroethane mixed solvent was added, and the mixture was further dispersed for 30 minutes. Spraying the thus obtained dispersion onto the CTL and drying it to form a charge generation layer with a thickness of 5 μm,
A photoreceptor having a photosensitive layer having a laminated structure was obtained. Comparative Example 2 A comparative photoreceptor was obtained in exactly the same manner as in Example 5 except that Exemplary Compound 8 was omitted. Example 6 A photoreceptor was obtained in exactly the same manner as in Example 5, except that Exemplified Compound 11 was used in place of Exemplified Compound 8. Example 7 A protective layer containing the same exemplified compound 8 as in Example 3 was placed on the photosensitive layer (same as the photoreceptor of Comparative Example 2) except for the exemplified compound 8 in Example 5, and a photoreceptor was obtained. Ta. Example 8 On the photosensitive layer excluding Exemplified Compound 8 of Example 5,
A protective layer containing Exemplified Compound 8 similar to that in Example 4 was provided to obtain a photoreceptor. The ozone resistance of the photoreceptor sample obtained as described above was evaluated using the following ozone fatigue tester. In other words, an electrostatic tester (manufactured by Kawaguchi Electric Seisakusho)
An apparatus was used in which an ozone generator (Model 0-1-2, manufactured by Nippon Ozone Co., Ltd.) and an ozone monitor (Model EG-2001, manufactured by Ebara Jitsugyo Co., Ltd.) were attached to an ozone generator (Model SP-428). The photoreceptor was mounted at an ozone concentration of 90 ppm, a voltage of +6KV was applied, the photosensitive layer was charged by corona discharge for 5 seconds, the photosensitive layer was left for 5 seconds (the potential at this time was set as the initial potential V 0 ), and then photosensitive Irradiate the layer surface with light from a tungsten lamp with an illuminance of 14 lux, and repeat this operation for 100 lux.
Repeatedly. When the potential after 100 irradiations is V 1 , V 1 /V 0 ×
Ozone resistance was expressed as 100 (%). V/V 0 indicates the degree of potential drop after 100 repetitions, and the larger the value, the better.
【表】
別表から本発明の感光体はいずれも耐オゾン性
がすぐれているのに対し、比較用感光体はオゾン
劣化が著しいことが判る。[Table] From the attached table, it can be seen that all of the photoreceptors of the present invention have excellent ozone resistance, whereas the comparative photoreceptors show significant ozone deterioration.
第１図ないし第３図は本発明の正帯電用感光体
の断面図である。
１……支持体、２……電荷輸送層、３……電荷
発生層、４……感光層、５……電荷輸送物質
（CTM）、６……電荷発生物質（CGM）、７……
保護層。
1 to 3 are cross-sectional views of the positively charging photoreceptor of the present invention. DESCRIPTION OF SYMBOLS 1...Support, 2...Charge transport layer, 3...Charge generation layer, 4...Photosensitive layer, 5...Charge transport material (CTM), 6...Charge generation material (CGM), 7...
protective layer.
Claims (1)
層、または電荷輸送層、電荷発生層及び保護層を
順次積層した電子写真感光体において、電荷発生
層中に電荷輸送物質を含有し、かつ少なくとも最
表面層中に下記一般式で示される化合物を含有す
ることを特徴とする正帯電用電子写真感光体。 一般式 【化】 〔式中、R1は水素原子、ヒドロキシル基または
アルコキシ基を表し、R2およびR3は各々、水素
原子またはアルキル基を表す。ただしR2および
R3が同時に水素原子であることはない。〕[Scope of Claims] 1. An electrophotographic photoreceptor in which a charge transport layer and a charge generation layer, or a charge transport layer, a charge generation layer, and a protective layer are sequentially laminated on a conductive support, in which a charge transport substance is contained in the charge generation layer. What is claimed is: 1. An electrophotographic photoreceptor for positive charging, characterized in that it contains a compound represented by the following general formula in at least its outermost layer. General formula: [In the formula, R 1 represents a hydrogen atom, a hydroxyl group, or an alkoxy group, and R 2 and R 3 each represent a hydrogen atom or an alkyl group. However, R 2 and
R 3 is never a hydrogen atom at the same time. ]
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24369986A JPS6396662A (en) | 1986-10-13 | 1986-10-13 | Positive electrifiable electrophotographic sensitive body |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24369986A JPS6396662A (en) | 1986-10-13 | 1986-10-13 | Positive electrifiable electrophotographic sensitive body |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6396662A JPS6396662A (en) | 1988-04-27 |
| JPH0567232B2 true JPH0567232B2 (en) | 1993-09-24 |
Family
ID=17107669
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP24369986A Granted JPS6396662A (en) | 1986-10-13 | 1986-10-13 | Positive electrifiable electrophotographic sensitive body |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6396662A (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6479752A (en) * | 1987-09-21 | 1989-03-24 | Seiko Epson Corp | Organic electrophotographic sensitive body |
| US5096793A (en) * | 1989-06-28 | 1992-03-17 | Minolta Camera Kabushiki Kaisha | Photosensitive member excellent in antioxidation |
| JP2990705B2 (en) * | 1989-10-05 | 1999-12-13 | ミノルタ株式会社 | Laminated photoreceptor |
| JP6024554B2 (en) * | 2013-03-26 | 2016-11-16 | 富士ゼロックス株式会社 | Electrophotographic photosensitive member, process cartridge, and image forming apparatus |
| JP6528596B2 (en) * | 2015-08-19 | 2019-06-12 | 富士ゼロックス株式会社 | Electrophotographic photosensitive member, process cartridge, image forming apparatus |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57122444A (en) * | 1981-01-23 | 1982-07-30 | Canon Inc | Electrophotographic receptor |
| JPS6135452A (en) * | 1984-07-27 | 1986-02-19 | Minolta Camera Co Ltd | Electrophotographic sensitive body |
-
1986
- 1986-10-13 JP JP24369986A patent/JPS6396662A/en active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57122444A (en) * | 1981-01-23 | 1982-07-30 | Canon Inc | Electrophotographic receptor |
| JPS6135452A (en) * | 1984-07-27 | 1986-02-19 | Minolta Camera Co Ltd | Electrophotographic sensitive body |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6396662A (en) | 1988-04-27 |
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