JPS6318741B2 - - Google Patents
Info
- Publication number
- JPS6318741B2 JPS6318741B2 JP16701680A JP16701680A JPS6318741B2 JP S6318741 B2 JPS6318741 B2 JP S6318741B2 JP 16701680 A JP16701680 A JP 16701680A JP 16701680 A JP16701680 A JP 16701680A JP S6318741 B2 JPS6318741 B2 JP S6318741B2
- Authority
- JP
- Japan
- Prior art keywords
- photoreceptor
- weight
- disazo pigment
- charge
- layer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 108091008695 photoreceptors Proteins 0.000 claims description 54
- 239000000049 pigment Substances 0.000 claims description 45
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 39
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 239000010410 layer Substances 0.000 description 56
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- 238000000034 method Methods 0.000 description 13
- 239000000126 substance Substances 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- 239000011230 binding agent Substances 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 239000006185 dispersion Substances 0.000 description 7
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 229920006267 polyester film Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 230000035945 sensitivity Effects 0.000 description 6
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 229920001225 polyester resin Polymers 0.000 description 4
- 239000004645 polyester resin Substances 0.000 description 4
- 229910052711 selenium Inorganic materials 0.000 description 4
- 239000011669 selenium Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- -1 1,3-bis(3-aminostyryl)benzene Chemical compound 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 229910001370 Se alloy Inorganic materials 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000010419 fine particle Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- QNLZIZAQLLYXTC-UHFFFAOYSA-N 1,2-dimethylnaphthalene Chemical compound C1=CC=CC2=C(C)C(C)=CC=C21 QNLZIZAQLLYXTC-UHFFFAOYSA-N 0.000 description 2
- HYGLETVERPVXOS-UHFFFAOYSA-N 1-bromopyrene Chemical compound C1=C2C(Br)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 HYGLETVERPVXOS-UHFFFAOYSA-N 0.000 description 2
- TURIHPLQSRVWHU-UHFFFAOYSA-N 2-phenylnaphthalene Chemical compound C1=CC=CC=C1C1=CC=C(C=CC=C2)C2=C1 TURIHPLQSRVWHU-UHFFFAOYSA-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
- CLQYLLIGYDFCGY-UHFFFAOYSA-N 4-(2-anthracen-9-ylethenyl)-n,n-diethylaniline Chemical compound C1=CC(N(CC)CC)=CC=C1C=CC1=C(C=CC=C2)C2=CC2=CC=CC=C12 CLQYLLIGYDFCGY-UHFFFAOYSA-N 0.000 description 2
- BZKRKPGZABEOSM-XMHGGMMESA-N 4-[(e)-2-[3-[4-(diethylamino)phenyl]-2-phenyl-3,4-dihydropyrazol-5-yl]ethenyl]-n,n-diethylaniline Chemical compound C1=CC(N(CC)CC)=CC=C1\C=C\C1=NN(C=2C=CC=CC=2)C(C=2C=CC(=CC=2)N(CC)CC)C1 BZKRKPGZABEOSM-XMHGGMMESA-N 0.000 description 2
- UZGVMZRBRRYLIP-UHFFFAOYSA-N 4-[5-[4-(diethylamino)phenyl]-1,3,4-oxadiazol-2-yl]-n,n-diethylaniline Chemical compound C1=CC(N(CC)CC)=CC=C1C1=NN=C(C=2C=CC(=CC=2)N(CC)CC)O1 UZGVMZRBRRYLIP-UHFFFAOYSA-N 0.000 description 2
- 239000004419 Panlite Substances 0.000 description 2
- 206010034972 Photosensitivity reaction Diseases 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 229910052980 cadmium sulfide Inorganic materials 0.000 description 2
- 239000002800 charge carrier Substances 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- GACNTLAEHODJKY-UHFFFAOYSA-N n,n-dibenzyl-4-[1-[4-(dibenzylamino)phenyl]propyl]aniline Chemical compound C=1C=C(N(CC=2C=CC=CC=2)CC=2C=CC=CC=2)C=CC=1C(CC)C(C=C1)=CC=C1N(CC=1C=CC=CC=1)CC1=CC=CC=C1 GACNTLAEHODJKY-UHFFFAOYSA-N 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 230000036211 photosensitivity Effects 0.000 description 2
- 239000002985 plastic film Substances 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- HSMFKWKHZVFTPZ-UHFFFAOYSA-N 1,3,7,9-tetranitro-5-oxidobenzo[c]cinnolin-5-ium Chemical compound C1=C([N+]([O-])=O)C=C2C3=C([N+]([O-])=O)C=C([N+](=O)[O-])C=C3[N+]([O-])=NC2=C1[N+]([O-])=O HSMFKWKHZVFTPZ-UHFFFAOYSA-N 0.000 description 1
- PMBBBTMBKMPOQF-UHFFFAOYSA-N 1,3,7-trinitrodibenzothiophene 5,5-dioxide Chemical compound O=S1(=O)C2=CC([N+](=O)[O-])=CC=C2C2=C1C=C([N+]([O-])=O)C=C2[N+]([O-])=O PMBBBTMBKMPOQF-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- WQGWMEKAPOBYFV-UHFFFAOYSA-N 1,5,7-trinitrothioxanthen-9-one Chemical compound C1=CC([N+]([O-])=O)=C2C(=O)C3=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C3SC2=C1 WQGWMEKAPOBYFV-UHFFFAOYSA-N 0.000 description 1
- KZEVSDGEBAJOTK-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[5-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]ethanone Chemical group N1N=NC=2CN(CCC=21)C(CC=1OC(=NN=1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O KZEVSDGEBAJOTK-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
- HJCNIHXYINVVFF-UHFFFAOYSA-N 2,6,8-trinitroindeno[1,2-b]thiophen-4-one Chemical compound O=C1C2=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C2C2=C1C=C([N+](=O)[O-])S2 HJCNIHXYINVVFF-UHFFFAOYSA-N 0.000 description 1
- VMQHOWOVMXIROE-UHFFFAOYSA-N 2,8-dinitrodibenzothiophene Chemical compound C1=C([N+]([O-])=O)C=C2C3=CC([N+](=O)[O-])=CC=C3SC2=C1 VMQHOWOVMXIROE-UHFFFAOYSA-N 0.000 description 1
- LPZOCVVDSHQFST-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-ethylpyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical group C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)CC LPZOCVVDSHQFST-UHFFFAOYSA-N 0.000 description 1
- ZHOQMEKSJLKZRY-UHFFFAOYSA-N 2-bromopyrene-1-carbaldehyde Chemical compound C1=CC=C2C=CC3=C(C=O)C(Br)=CC4=CC=C1C2=C43 ZHOQMEKSJLKZRY-UHFFFAOYSA-N 0.000 description 1
- WGRSVHBSCVGKDP-UHFFFAOYSA-N 2-ethyl-9h-carbazole-1-carbaldehyde Chemical compound C1=CC=C2C3=CC=C(CC)C(C=O)=C3NC2=C1 WGRSVHBSCVGKDP-UHFFFAOYSA-N 0.000 description 1
- KLLLJCACIRKBDT-UHFFFAOYSA-N 2-phenyl-1H-indole Chemical compound N1C2=CC=CC=C2C=C1C1=CC=CC=C1 KLLLJCACIRKBDT-UHFFFAOYSA-N 0.000 description 1
- PAEVCXCHJVISEP-UHFFFAOYSA-N 3-n,3-n,6-n,6-n-tetrabenzyl-9-ethylcarbazole-3,6-diamine Chemical compound C=1C=C2N(CC)C3=CC=C(N(CC=4C=CC=CC=4)CC=4C=CC=CC=4)C=C3C2=CC=1N(CC=1C=CC=CC=1)CC1=CC=CC=C1 PAEVCXCHJVISEP-UHFFFAOYSA-N 0.000 description 1
- MLEBCZSWVARRML-UHFFFAOYSA-N 4-(2,5-diphenyl-1,3-oxazol-4-yl)-n,n-diethylaniline Chemical compound C1=CC(N(CC)CC)=CC=C1C1=C(C=2C=CC=CC=2)OC(C=2C=CC=CC=2)=N1 MLEBCZSWVARRML-UHFFFAOYSA-N 0.000 description 1
- YATJOUUMQREMEW-UHFFFAOYSA-N 4-(2-anthracen-9-ylethenyl)-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1C=CC1=C(C=CC=C2)C2=CC2=CC=CC=C12 YATJOUUMQREMEW-UHFFFAOYSA-N 0.000 description 1
- LXQJOJHWKDPNPD-UHFFFAOYSA-N 4-[2-[6-[2-[4-(diethylamino)phenyl]ethenyl]pyridin-2-yl]ethenyl]-n,n-diethylaniline Chemical compound C1=CC(N(CC)CC)=CC=C1C=CC1=CC=CC(C=CC=2C=CC(=CC=2)N(CC)CC)=N1 LXQJOJHWKDPNPD-UHFFFAOYSA-N 0.000 description 1
- SBMCZDLOXDWNIN-UHFFFAOYSA-N 4-[bis[4-(diethylamino)phenyl]methyl]-n,n-diethylaniline Chemical compound C1=CC(N(CC)CC)=CC=C1C(C=1C=CC(=CC=1)N(CC)CC)C1=CC=C(N(CC)CC)C=C1 SBMCZDLOXDWNIN-UHFFFAOYSA-N 0.000 description 1
- SCHUFJWXJINKKV-UHFFFAOYSA-N 9-ethyl-3-fluoren-9-ylidene-2h-carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2C1=C1C=C2C3=CC=CC=C3N(CC)C2=CC1 SCHUFJWXJINKKV-UHFFFAOYSA-N 0.000 description 1
- PLAZXGNBGZYJSA-UHFFFAOYSA-N 9-ethylcarbazole Chemical compound C1=CC=C2N(CC)C3=CC=CC=C3C2=C1 PLAZXGNBGZYJSA-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical group O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- MUBKMWFYVHYZAI-UHFFFAOYSA-N [Al].[Cu].[Zn] Chemical compound [Al].[Cu].[Zn] MUBKMWFYVHYZAI-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- OKVJWADVFPXWQD-UHFFFAOYSA-N difluoroborinic acid Chemical compound OB(F)F OKVJWADVFPXWQD-UHFFFAOYSA-N 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
- 238000007598 dipping method Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- NQJCMNDQTUKOOR-UHFFFAOYSA-N n,n-dibenzyl-4-(fluoren-9-ylidenemethyl)aniline Chemical compound C=1C=CC=CC=1CN(C=1C=CC(C=C2C3=CC=CC=C3C3=CC=CC=C32)=CC=1)CC1=CC=CC=C1 NQJCMNDQTUKOOR-UHFFFAOYSA-N 0.000 description 1
- HDSOVOUJTLABJR-UHFFFAOYSA-N n,n-diethyl-4-(5-naphthalen-1-yl-1,3,4-oxadiazol-2-yl)aniline Chemical compound C1=CC(N(CC)CC)=CC=C1C1=NN=C(C=2C3=CC=CC=C3C=CC=2)O1 HDSOVOUJTLABJR-UHFFFAOYSA-N 0.000 description 1
- ZOOOVTVHHIPVET-UHFFFAOYSA-N n,n-diethyl-4-[2-(5-methyl-1,3-benzoxazol-2-yl)ethenyl]aniline Chemical compound C1=CC(N(CC)CC)=CC=C1C=CC1=NC2=CC(C)=CC=C2O1 ZOOOVTVHHIPVET-UHFFFAOYSA-N 0.000 description 1
- CIPHTOQKGSLCLV-UHFFFAOYSA-N n-phenylnaphthalene-1-carboxamide Chemical compound C=1C=CC2=CC=CC=C2C=1C(=O)NC1=CC=CC=C1 CIPHTOQKGSLCLV-UHFFFAOYSA-N 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 150000003071 polychlorinated biphenyls Chemical group 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001470 polyketone Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 229920006215 polyvinyl ketone Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003334 secondary amides Chemical class 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical group C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-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
- 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
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Photoreceptors In Electrophotography (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
本発明は電子写真用感光体に関し、更に詳しく
はジスアゾ顔料を含有する感光層を有する新規な
感光体に関する。
従来電子写真用感光体として、無定形セレン、
セレン合金、硫化カドミウム、酸化亜鉛等の無機
系光導電材料、ポリビニルカルバゾールやその誘
導体が広く知られている。
無定形セレンあるいはセレン合金は電子写真用
感光体として極めて優れた特性を有し、広く実用
化されていることは周知である。しかし、無定形
セレンの感光波長領域は、青色領域であり、赤色
領域にはほとんど感度を有さない。又感光性を長
波長領域に広げるために種々の方法が提案されて
いるが、感光波長域の選択には制約が多く、長波
長光に対する感光性は充分ではない。酸化亜鉛あ
るいは硫化カドミウムを感光体として用いる場合
も、それ自体の感光波長領域は狭く、実用に供す
る為には種々の増感剤の添加が必要である。
有機光導電材料として広く知られているポリビ
ニルカルバゾールは透明性、皮膜形成性、可撓
性、正孔輸送性などの点で優れているが、ポリビ
ニルカルバゾール自体は可視光領域400〜700nｍ
にはほとんど感度を有さないなどの欠点がある。
これらの欠点を改良したものとして特公昭50−
10496号公報にポリビニルカルバゾールと２，４，
７−トリニトロフルオレノンで電荷移動錯体を形
成させた感光体が開示されている。
その他無定形セレンあるいはセレン合金を電荷
発生層とし、これに電荷移動層を積層し、それぞ
れの層に役割を分担させた感光体として特公昭45
−5349号公報、特公昭49−3168号公報、特公昭50
−14914号公報、特公昭51−10982号公報等が挙げ
られる。
その他種々の顔料を電荷発生層としその上に電
荷移動層を設けた次のような感光体が開発されて
いる。USP3837851には電荷発生層と少なくとも
１つのトリアリルピラゾリンを含有する電荷移動
層を有する感光体、USP3850630には透明な電荷
移動層とインジゴイド顔料からなる電荷発生層と
からなる感光体、USP3871882にはペリレン顔料
の誘導体からなる電荷発生層と３−ブロムピレン
とフオルムアルデヒドの縮合体からなる電荷移動
層とからなる感光体、特開昭53−133445号公報に
な透明な電荷移動層とスチルベン骨格を有するジ
スアゾ顔料からなる電荷発生層で構成される感光
体が開示されている。これらの感光体の一部はす
でに市場において実施されているものがあるが、
まだ種々の性質を充分満足させる感光体が得られ
ていないのが現状である。
本発明者等は、種々研究をかさねた結果、後記
一般式で表わされる化合物が、電子写真感光体の
電荷発生物質あるいは光導電性物質として有効に
働くことをみいだし本発明を完成するにいたつ
た。
本発明の主要な目的は短波長側に優れた感度を
有する電荷担体発生物質を提供することにより可
視光領域において優れた再現性を有する電子写真
感光体を提供することである。
すなわち、本発明は導電性支持体上に、下記一
般式
〔但し、Ａは
The present invention relates to an electrophotographic photoreceptor, and more particularly to a novel photoreceptor having a photosensitive layer containing a disazo pigment. Conventionally, amorphous selenium,
Inorganic photoconductive materials such as selenium alloys, cadmium sulfide, and zinc oxide, polyvinyl carbazole, and derivatives thereof are widely known. It is well known that amorphous selenium or selenium alloys have extremely excellent properties as electrophotographic photoreceptors and are widely used in practical use. However, the sensitive wavelength region of amorphous selenium is the blue region and has almost no sensitivity in the red region. Various methods have been proposed to extend the photosensitivity to long wavelengths, but there are many restrictions on the selection of the sensitive wavelength range, and the photosensitivity to long wavelengths is not sufficient. Even when zinc oxide or cadmium sulfide is used as a photoreceptor, its sensitivity wavelength range is narrow, and it is necessary to add various sensitizers for practical use. Polyvinylcarbazole, which is widely known as an organic photoconductive material, is excellent in terms of transparency, film-forming properties, flexibility, and hole transport properties, but polyvinylcarbazole itself has a visible light range of 400 to 700 nm.
has the disadvantage of having almost no sensitivity. To improve these shortcomings, the Special Public Service was developed in the 1970s.
No. 10496 describes polyvinylcarbazole and 2,4,
A photoreceptor is disclosed in which a charge transfer complex is formed with 7-trinitrofluorenone. In addition, as a photoreceptor in which amorphous selenium or selenium alloy is used as a charge generation layer and a charge transfer layer is laminated on this, each layer has a role.
-5349 Publication, Special Publication No. 1977-3168, Special Publication No. 1973
-14914, Japanese Patent Publication No. 51-10982, etc. In addition, the following photoreceptors have been developed in which a charge generation layer is made of various pigments and a charge transfer layer is provided thereon. USP 3837851 describes a photoreceptor having a charge generation layer and a charge transfer layer containing at least one triallylpyrazoline; USP 3850630 describes a photoreceptor comprising a transparent charge transfer layer and a charge generation layer comprising an indigoid pigment; A photoreceptor consisting of a charge generation layer made of a perylene pigment derivative and a charge transfer layer made of a condensate of 3-bromopyrene and formaldehyde, disclosed in JP-A-53-133445, has a transparent charge transfer layer and a stilbene skeleton. A photoreceptor is disclosed comprising a charge generating layer comprising a disazo pigment. Some of these photoreceptors are already in use on the market;
At present, a photoreceptor that satisfactorily satisfies various properties has not yet been obtained. As a result of various studies, the present inventors have discovered that the compound represented by the general formula below works effectively as a charge-generating substance or a photoconductive substance for electrophotographic photoreceptors, and have completed the present invention. Ivy. The main object of the present invention is to provide an electrophotographic photoreceptor that has excellent reproducibility in the visible light region by providing a charge carrier generating material that has excellent sensitivity on the short wavelength side. That is, the present invention provides the following general formula on a conductive support: [However, A is
【式】【formula】
【式】または[expression] or
【式】
（ここで、Ｘはベンゼン環、ナフタレン環などの
芳香環、インドール環、カルバゾール環、ベンゾ
フラン環などの複素環またはそれらの置換体、
Ar1はベンゼン環、ナフタレン環などの芳香環、
ジベンゾフランなどの複素還又はそれらの置換
体、Ar2およびAr3はベンゼン環、ナフタレン環
などの芳香環またはそれらの置換体、R1および
R2は水素、低級アルキル基、フエニル基または
その置換体、R2は低級アルキル基、カルボキシ
ル基またはそのエステルを表わす）を表わす。〕
で示されるジスアゾ顔料を有効成分として含有す
る感光層を有することを特徴とする電子写真用感
光体を提供するものである。
本発明で使用される上記一般式の化合物の具体
例を構造式で示すとつぎのとおりである。
これらのジスアゾ顔料は新規化合物であり、
１，３−ビス（３−アミノスチリル）ベンゼンを
ジアゾ化してテトラゾニウム塩として単離したの
ち、これを適当な有機溶媒、例えばＮ，Ｎ−ジメ
チルホルムアミド中で、前述の各顔料に対応する
カツプラーとアルカリとの存在下でカツプリング
反応させることにより製造することができる。例
えば前記No.１の顔料の製造法は下記の通りであ
る。
製造例
水1200mlと濃塩酸60mlとよりなる希塩酸中へ、
１，３−ビス（３−アミノスチリル）ベンゼン
28.0ｇを加え、60℃で30分撹拌した後、０℃まで
冷却した。ついでこれに亜硝酸ナトリウム13.0ｇ
を水40mlに溶解した溶液を０〜３℃で40分を要し
て滴下した。その後同温度で30分撹拌した後、微
量の不溶物を濾過除去した。この濾液中に42％硼
弗化水素酸50mlを添加し、析出した結晶を濾別、
水洗、乾燥して43.1ｇ（収率91.8％）のテトラゾ
ニウムジフルオロボレートの黄色結晶を得た。分
解点70℃以上、赤外線吸収スペクトル（KBr錠
剤法）では2250cm-1にN2に基づく吸収率が965cm
-1にトランスの−CH＝CH−に基づく吸収帯が認
められた。
つぎにこうして得られたテトラゾニウム塩3.0
ｇおよびカツプラーとして２−ヒドロキシ−３−
ナフトエ酸アニリド3.3ｇを、冷却したＮ，Ｎ−
ジメチルホルムアミド390ml中に溶解し、これに
酢酸ナトリウム1.9ｇおよび水20mlからなる溶液
を４〜８℃の温度で一時間に亘つて滴下したのち
室温で約３時間撹拌する。その後沈澱を濾取し、
300mlのジオキサンで７回洗浄後、水300mlで２回
洗浄し、得られる赤色の結晶を２mmHgの減圧下、
70℃の温度で乾燥し、No.１のジスアゾ顔料3.9ｇ
（収率75.6％）を得る。融点250℃以上である。
元素分析の結果は下記の通りである。
計算値(%) 実測値(%)
Ｃ78.11 77.85
Ｈ4.69 4.70
Ｎ9.76 9.52
また、IR吸収スペクトル（KBr錠剤法）では
1670cm-1に第２アミドに基づく吸収が、955cm-1
にトランスの−CH＝CH−に基づく吸収が認め
られた。
本発明の感光体は以上のようなジスアゾ顔料を
含むものであるが、これらの顔料の応用の仕方に
よつて、第１〜３図の形態をとることができる。
第１図の感光体は導電性支持体１上にジスアゾ
顔料３を主体とする電荷発生層５と電荷移動物質
を主体とする電荷移動層６とからなつている。
第１図の感光体では、像露光された光は電荷移
動層を透過し、電荷発生層５に到達し、その部分
のジスアゾ顔料３で電荷の生成が起こり、一方、
電荷移動層６は電荷の注入を受けその移動を行な
うもので、光減衰に必要な電荷の生成はジスアゾ
顔料で、また電荷の移動は電荷移動層でというメ
カニズムである。
第２図の感光体は導電性支持体１上に主として
ジスアゾ顔料３、電荷移動物質および絶縁性結合
剤よりなる電荷移動媒体４からなる感光層２′を
設けたものである。ここでもジスアゾ顔料は電荷
発生物質である。その他の感光体として第１図の
電荷発生層と電荷移動層を逆にすることも可能で
ある。
第３図の感光体は導電性支持体１上にジスアゾ
顔料３（ここでは光導電性物質として使用され
る）と絶縁性結合剤とからなる感光層２″を設け
たものである。
第１図の感光体を作成するには、導電性支持体
上にジスアゾ顔料をUSP3973959、USP3996049
等に記載されている真空蒸着方法で真空蒸着する
か、あるいはジスアゾ顔料の微粒子を必要とあれ
ば結合剤を溶解した適当な溶剤中に分散し、これ
を導電性支持体上に塗布乾燥し、更に必要とあれ
ば例えば特開昭51−90827に示されているような
バフ研摩等の方法により表面仕上をするか、膜厚
を調整した後、電荷移動性物質及び結合剤を含む
溶液を塗布乾燥して得られる。
第２図の感光体を作成するにはジスアゾ顔料の
微粒子を電荷移動物質及び結合剤を溶解した溶液
中に分散せしめ、これを導電性支持体上に塗布乾
燥すればよい。
第３図の感光体を作成するにはジスアゾ顔料の
微粒子を結合剤溶液中に分散した液を導電性支持
体上に塗布乾燥すればよい。
上記いずれの場合も本発明に使用されるジスア
ゾ顔料はボールミル等により粒径5μ以下好まし
くは2μ以下に粉砕して用いられる。塗布方法は
通常の手段、例えばドクターブレード、デイツピ
ング、ワイヤーバーなどで行なう。
感光層の厚さは、第１図のもので電荷発生層の
厚みは0.01〜5μ、好ましくは0.05〜2μである。こ
の厚さが0.01μ以下であると電荷の発生は十分で
はなく、また5μ以上であると残留電位が高く実
用に耐えない。電荷移動層の厚さは３〜50μ、好
ましくは５〜20μである。この厚さが3μ以下であ
ると帯電量が不十分であり、50μ以上であると残
留電位が高く実用的ではない。また電荷移動層中
の電荷移動物質の割合は10〜95重量％、好ましく
は30〜90重量％である。電荷移動物質の占める割
合が10重量％以下であると、電荷の移動はほとん
ど行なわれず、また95重量％以上であると感光体
皮膜の機械的強度が極めて悪く実用に供しえな
い。
また第３図の感光体において感光層の厚さは約
３〜50μ、好ましくは５〜20μであり、感光層中
のジスアゾ顔料の割合は感光層に対し30〜70重量
％、好ましくは約50重量％が適当である。
なお第１〜３図のいずれの感光体を作成する場
合にも結合剤と共に可塑剤を用いることができ
る。
本発明の感光体において使用される導電性支持
体としては、アルミニウム、銅、亜鉛等の金属
板、ポリエステル等のプラスチツクシートまたは
プラスチツクフイルムにアルミニウム、SnO2等
の導電材料を蒸着したもの、あるいは導電処理し
た紙等が使用される。
結合剤としては、ポリアミド、ポリウレタン、
ポリエステル、エポキシ樹脂、ポリケトン、ポリ
カーボネートなどの結合系樹脂やポリビニルケト
ン、ポリスチレン、ポリ−Ｎ−ビニルカルバゾー
ル、ポリアクリルアミドなどのビニル重合体など
が挙げられるが、絶縁性で且つ接着性のある樹脂
は全て使用できる。
可塑剤としては、ハロゲン化パラフイン、ポリ
塩化ビフエニル、ジメチルナフタレン、ジブチル
フタレートなどが挙げられる。その他感光体の表
面性をよくするためにシリコンオイル等を加えて
もよい。
また電荷移動物質としては高分子のものではポ
リ−Ｎ−ビニルカルバゾール、ポリビニルインド
ロキノキサリン、ポリビニルジベンゾチオフエ
ン、ポリビニルアントラセン、ポリビニルアクリ
ジンなどのビニル重合体やブロムピレン〜ホルム
アルデヒド樹脂、エチルカルバゾール〜ホルムア
ルデヒド樹脂などの縮合樹脂が、また低分子（単
量体）のものでは２，４，７−トリニトロ−９−
フルオレノン、２，６，８−トリニトロ−4H−
インデノ〔１，２−ｂ〕チオフエン−４−オン、
２，８−ジニトロジベンゾチオフエン、１，３，
７−トリニトロジベンゾチオフエン−５，５−ジ
オキサイド、１，３，７，９−テトラニトロベン
ゾ〔ｃ〕シンノリン−５−オキサイド、２，４，
８−トリニトロチオキサントン、１−ブロムピレ
ン、Ｎ−エチルカルバゾール、２−フエニルイン
ドール、２−フエニルナフタレン、２，５−ビス
（４−ジエチルアミノフエニル）−１，３，４−オ
キサジアゾール、２，２−ビス（４−ジエチルア
ミノフエニル）−１，３，４−トリアゾール、１
−フエニル−３−（４−ジエチルアミノスチリル）
−５−（４−ジエチルアミノフエニル）ピラゾリ
ン、２−フエニル−４−（４−ジエチルアミノフ
エニル）−５−フエニルオキサゾール、トリフエ
ニルアミン、トリス（４−ジエチルアミノフエニ
ル）メタン、３，６−ビス（ジベンジルアミノ）
−９−エチルカルバゾール、４，4′−ビス（ジベ
ンジルアミノ）ジフエニルメタン、４，4′−ビス
（ジベンジルアミノ）ジフエニルエーテル、１，
１−ビス（４−ジベンジルアミノフエニル）プロ
パン、２−（α−ナフチル）−５−（４−ジエチル
アミノフエニル）−１，３，４−オキサジアゾー
ル、２−スチリル−５−（３−Ｎ−エチルカルバ
ゾリル）−１，３，４−オキサジアゾール、２−
（４−メトキシフエニル）−５−（３−Ｎ−エチル
カルバゾリル）−１，３，４−オキサジアゾール、
２−（４−ジエチルアミノフエニル）−５−（３−
Ｎ−エチルカルバゾリル）−１，３，４−オキサ
ジアゾール、９−（４−ジエチルアミノスチリル）
アントラセン、９−（４−ジメチルアミノスチリ
ル）アントラセン、α−（９−アントリル）−β−
（３−Ｎ−エチルカルバゾリル）エチレン、５−
メチル−２−（４−ジエチルアミノスチリル）ベ
ンゾオキサゾール、９−（４−ジベンジルアミノ
ベンジリデン）フルオレン、Ｎ−エチル−３−
（９−フルオレニリデン）カルバゾール、２，６
−ビス（４−ジエチルアミノスチリル）ピリジ
ン、メチルフエニルヒドラゾン−３−メチリデン
−９−エチルカルバゾール、メチルフエニルヒド
ラゾン−４−メチリデン−Ｎ，N′−ジエチルア
ニリンなどが挙げられる。これらの電荷移動物質
は単独又は２種以上混合して用いられる。最適の
電荷移動物質は使用されるジスアゾ顔料によつて
変化する。理由は不明であるが、或るジスアゾ顔
料は或る電荷移動物質と組みあわせた場合に最も
適した電子写真用感光体を提供する。
なお、以上のようにして得られる感光体にはい
ずれも導電性支持体と感光層の間に必要に応じて
接着層又はバリヤ層を設けることができる。これ
らの層に用いられる材料としてはポリアミド、ニ
トロセルロース、酸化アルミニウムなどが適当
で、また膜厚は1μ以下が好ましい。
本発明の感光体を用いて複写を行なうには、感
光層面に帯電、露光を旋した後、現像を行ない、
必要によつて、紙などへ転写を行うことにより達
成される。
本発明の感光体は短波長側の感度が高く、また
可撓性に富むなどのすぐれた利点を有する。
以下に実施例を示す。
実施例 １
No.５のジスアゾ顔料２重量部及びテトラヒドロ
フラン98重量部をボールミル中で粉砕混合し、得
られた分散液をアルミニウム蒸着ポリエステルフ
イルム上にドクターブレードで塗布し自然乾燥し
て厚さ1μの電荷発生層を形成した。一方、９−
（４−ジエチルアミノスチリル）アントラセン２
重量部、ポリカーボネート樹脂〔(株)テイジン製、
パンライトＬ〕２重量部をテトラヒドロフラン16
重量部に溶解しこれを前記電荷発生層上にドクタ
ーブレードで塗布し120℃で10分間乾燥して厚さ
11μの電荷移動層を形成せしめ第１図の積層型感
光体を得た。
次にこの感光体の感光層面に市販の静電複写紙
試験装置により−6KVのコロナ放電を20秒間行
なつて負帯電させた後、20秒間暗所に放置し、そ
の時の表面電位Vpo（ボルト）を測定し、ついで
タングステンランプから、その表面が照度20ルツ
クスになるよう感光層に光照射を施し、その表面
電位がVpoの1/2になる迄の時間（秒）を求めて
半減露光時間Ｔ1/2（秒）とした。その結果
｛Vpo−1090ボルト、Ｔ1/21.6秒｝であつた。
さらに、同様に負帯電、暗所放置しVpo（ボル
ト）を測定し、ついで620nｍ以上の光をカツト
するフイルターを通した光を感光層に照射し、そ
の表面電位がV′poの1/2になる迄の時間（秒）を
求めて半減露光時間Ｔ1/2（秒）とした。
その結果｛V′po−1090ボルト、T′1/21.7秒｝
であつた。
T′1/2／Ｔ1/2＝1.06であり短波長側の感度が優
れていることが示された。
さらに、この感光体を市販の複写機（(株)リコー
製Ｐ−500）に用い、コピーを行ない黒色原稿部
（コダツク・グレースケール1.6）及び赤色原稿部
（コダツク・カラーコントロールパツチ、ブライ
マリーレツド）の画像濃度をマクベス濃度計で測
定した。
黒色原稿部 1.1
赤色原稿部 0.9
比較例
実施例１のNo.５のジスアゾ顔料のかわりに特開
昭47−37543に記載のクロルダイアンブルーを用
いた他は実施例１と全く同様に操作し積層型感光
体を得た。次いで、この感光体を用いT′1/2／Ｔ
１／２をもとめた。
T′1/2／Ｔ1/2＝1.83
また実施例１と同様にして画像濃度をもとめ
た。
黒色画像部 1.1
赤色画像部 0.4
このことより本発明の電荷発生物質を電子写真
感光体に用いることにより赤色画像部においても
優れた再現性を有することが理解される。
実施例 ２
No.１のジスアゾ顔料１重量部、ポリエステル樹
脂（(株)東洋紡製パイロン200）0.5重量パーセント
のテトラヒドロフラン溶液66重量部をボールミル
中で粉砕混合し、得られた分散液を、アルミニウ
ムを蒸着したポリエステルフイルム上にドクター
ブレードを用いて塗布し、80℃で２分間乾燥して
厚さ0.7μの電荷発生層を形成した。
一方、１，１−ビス（４−ジベンジルアミノフ
エニル）プロパン２重量部、ポーカーボネート樹
脂（(株)テイジン製パンライトＫ−1300）２重量部
をテトラヒドロフラン16重量部に溶解しこれを前
記電荷発生層上にドクターブレードで塗布し、
120℃で10分間乾燥して厚さ13μの電荷移動層を
形成せしめ第１図の積層型感光体を得た。次い
で、実施例１と全く同様にしてT′1/2／Ｔ1/2を
求めた。
T′1/2／Ｔ1/2＝1.03
実施例 ３〜５
実施例２においてNo.１のジスアゾ顔料のかわり
に下記表−１に示す番号のジスアゾ顔料を用いた
他は全く同様に操作し、第１図の感光体を作成
し、同じ方法でT′1/2／Ｔ1/2を求め表−１の結
果を得た。[Formula] (wherein,
Ar 1 is an aromatic ring such as a benzene ring or a naphthalene ring,
Heterocycles such as dibenzofuran or their substituents, Ar 2 and Ar 3 are aromatic rings such as benzene rings and naphthalene rings or their substituents, R 1 and
R 2 represents hydrogen, a lower alkyl group, a phenyl group, or a substituted product thereof; R 2 represents a lower alkyl group, a carboxyl group, or an ester thereof; ] The present invention provides an electrophotographic photoreceptor characterized by having a photosensitive layer containing a disazo pigment represented by the following as an active ingredient. Specific examples of the compounds having the above general formula used in the present invention are shown in the following structural formulas. These disazo pigments are new compounds,
After diazotizing 1,3-bis(3-aminostyryl)benzene and isolating it as a tetrazonium salt, it is mixed with couplers corresponding to each of the above-mentioned pigments in a suitable organic solvent, such as N,N-dimethylformamide. It can be produced by coupling reaction in the presence of an alkali. For example, the method for producing pigment No. 1 is as follows. Production example: Into dilute hydrochloric acid consisting of 1200ml of water and 60ml of concentrated hydrochloric acid,
1,3-bis(3-aminostyryl)benzene
After adding 28.0 g and stirring at 60°C for 30 minutes, the mixture was cooled to 0°C. Next, add 13.0g of sodium nitrite to this.
A solution prepared by dissolving . After stirring at the same temperature for 30 minutes, trace amounts of insoluble matter were removed by filtration. 50 ml of 42% borohydrofluoric acid was added to this filtrate, and the precipitated crystals were separated by filtration.
After washing with water and drying, 43.1 g (yield: 91.8%) of yellow crystals of tetrazonium difluoroborate were obtained. The decomposition point is 70℃ or higher, and the absorption rate based on N2 is 965 cm at 2250 cm -1 in the infrared absorption spectrum (KBr tablet method).
An absorption band based on trans -CH=CH- was observed in -1 . Next, the tetrazonium salt 3.0 obtained in this way
g and 2-hydroxy-3- as coupler
3.3 g of naphthoic acid anilide was cooled with N,N-
The mixture was dissolved in 390 ml of dimethylformamide, and a solution consisting of 1.9 g of sodium acetate and 20 ml of water was added dropwise thereto at a temperature of 4 to 8 DEG C. over an hour, followed by stirring at room temperature for about 3 hours. After that, the precipitate was collected by filtration,
After washing seven times with 300 ml of dioxane and twice with 300 ml of water, the resulting red crystals were washed under a reduced pressure of 2 mmHg.
Dry at a temperature of 70℃, No. 1 disazo pigment 3.9g
(yield 75.6%). Melting point is 250℃ or higher. The results of elemental analysis are as follows. Calculated value (%) Actual value (%) C78.11 77.85 H4.69 4.70 N9.76 9.52 In addition, in the IR absorption spectrum (KBr tablet method)
The absorption based on secondary amide at 1670cm -1 is 955cm -1
Absorption based on trans -CH=CH- was observed. The photoreceptor of the present invention contains the above-mentioned disazo pigments, and can take the forms shown in FIGS. 1 to 3 depending on the application of these pigments. The photoreceptor shown in FIG. 1 comprises a conductive support 1 and a charge generation layer 5 mainly composed of a disazo pigment 3 and a charge transfer layer 6 mainly composed of a charge transfer substance. In the photoreceptor shown in FIG. 1, the imagewise exposed light passes through the charge transfer layer and reaches the charge generation layer 5, where generation of charges occurs in the disazo pigment 3, and on the other hand,
The charge transfer layer 6 receives and transfers charges, and the mechanism is such that the charges necessary for light attenuation are generated by the disazo pigment, and the charges are transferred by the charge transfer layer. The photoreceptor shown in FIG. 2 has a photosensitive layer 2' formed on a conductive support 1, which mainly comprises a disazo pigment 3, a charge transfer medium 4 consisting of a charge transfer substance and an insulating binder. Again, the disazo pigment is a charge generating material. For other photoreceptors, it is also possible to reverse the charge generation layer and the charge transfer layer shown in FIG. The photoreceptor shown in FIG. 3 has a photosensitive layer 2'' consisting of a disazo pigment 3 (here used as a photoconductive material) and an insulating binder on a conductive support 1. To create the photoreceptor shown in Figure USP 3973959, USP 3996049 disazo pigment on a conductive support.
Alternatively, fine particles of a disazo pigment are dispersed in a suitable solvent in which a binder is dissolved if necessary, and this is coated on a conductive support and dried. If necessary, the surface is finished by buffing as shown in JP-A-51-90827, or after adjusting the film thickness, a solution containing a charge-transfer substance and a binder is applied. Obtained by drying. The photoreceptor shown in FIG. 2 can be prepared by dispersing fine particles of a disazo pigment in a solution containing a charge transfer substance and a binder, and coating the dispersion on a conductive support and drying it. In order to produce the photoreceptor shown in FIG. 3, a solution in which fine particles of a disazo pigment are dispersed in a binder solution is coated on a conductive support and dried. In any of the above cases, the disazo pigment used in the present invention is used after being ground to a particle size of 5 μm or less, preferably 2 μm or less, using a ball mill or the like. Application may be carried out by conventional means, such as a doctor blade, dipping, wire bar, etc. The thickness of the photosensitive layer is as shown in FIG. 1, and the thickness of the charge generating layer is 0.01 to 5 .mu.m, preferably 0.05 to 2 .mu.m. If the thickness is less than 0.01μ, charge generation will not be sufficient, and if it is more than 5μ, the residual potential will be too high for practical use. The thickness of the charge transport layer is 3 to 50 microns, preferably 5 to 20 microns. If the thickness is less than 3μ, the amount of charge will be insufficient, and if it is more than 50μ, the residual potential will be too high to be practical. The proportion of the charge transfer substance in the charge transfer layer is 10 to 95% by weight, preferably 30 to 90% by weight. When the proportion of the charge transfer substance is less than 10% by weight, almost no charge transfer occurs, and when it is more than 95% by weight, the mechanical strength of the photoreceptor film is so poor that it cannot be put to practical use. Further, in the photoreceptor shown in FIG. 3, the thickness of the photosensitive layer is about 3 to 50 μm, preferably 5 to 20 μm, and the proportion of the disazo pigment in the photosensitive layer is 30 to 70% by weight, preferably about 50 μm. Weight % is appropriate. Note that a plasticizer can be used together with a binder when producing any of the photoreceptors shown in FIGS. 1 to 3. The conductive support used in the photoreceptor of the present invention may be a metal plate made of aluminum, copper, zinc, etc., a plastic sheet made of polyester, or a plastic film on which a conductive material such as aluminum or SnO 2 is deposited, or a conductive support. Treated paper, etc. is used. As a binder, polyamide, polyurethane,
Examples include bonding resins such as polyester, epoxy resin, polyketone, and polycarbonate, and vinyl polymers such as polyvinyl ketone, polystyrene, poly-N-vinylcarbazole, and polyacrylamide, but all resins that are insulating and adhesive are used. Can be used. Examples of the plasticizer include halogenated paraffin, polychlorinated biphenyl, dimethylnaphthalene, and dibutyl phthalate. In addition, silicone oil or the like may be added to improve the surface properties of the photoreceptor. In addition, charge transfer substances include polymers such as vinyl polymers such as poly-N-vinylcarbazole, polyvinylindoquinoxaline, polyvinyldibenzothiophene, polyvinylanthracene, and polyvinylacridine, bromopyrene-formaldehyde resin, ethylcarbazole-formaldehyde resin, etc. condensation resin, and low molecular weight (monomer) 2,4,7-trinitro-9-
Fluorenone, 2,6,8-trinitro-4H-
indeno[1,2-b]thiophen-4-one,
2,8-dinitrodibenzothiophene, 1,3,
7-trinitrodibenzothiophene-5,5-dioxide, 1,3,7,9-tetranitrobenzo[c]cinnoline-5-oxide, 2,4,
8-trinitrothioxanthone, 1-bromopyrene, N-ethylcarbazole, 2-phenylindole, 2-phenylnaphthalene, 2,5-bis(4-diethylaminophenyl)-1,3,4-oxadiazole, 2,2-bis(4-diethylaminophenyl)-1,3,4-triazole, 1
-Phenyl-3-(4-diethylaminostyryl)
-5-(4-diethylaminophenyl)pyrazoline, 2-phenyl-4-(4-diethylaminophenyl)-5-phenyloxazole, triphenylamine, tris(4-diethylaminophenyl)methane, 3,6- Bis(dibenzylamino)
-9-ethylcarbazole, 4,4'-bis(dibenzylamino)diphenylmethane, 4,4'-bis(dibenzylamino)diphenyl ether, 1,
1-bis(4-dibenzylaminophenyl)propane, 2-(α-naphthyl)-5-(4-diethylaminophenyl)-1,3,4-oxadiazole, 2-styryl-5-(3 -N-ethylcarbazolyl)-1,3,4-oxadiazole, 2-
(4-methoxyphenyl)-5-(3-N-ethylcarbazolyl)-1,3,4-oxadiazole,
2-(4-diethylaminophenyl)-5-(3-
N-ethylcarbazolyl)-1,3,4-oxadiazole, 9-(4-diethylaminostyryl)
Anthracene, 9-(4-dimethylaminostyryl)anthracene, α-(9-anthryl)-β-
(3-N-ethylcarbazolyl)ethylene, 5-
Methyl-2-(4-diethylaminostyryl)benzoxazole, 9-(4-dibenzylaminobenzylidene)fluorene, N-ethyl-3-
(9-fluorenylidene)carbazole, 2,6
-bis(4-diethylaminostyryl)pyridine, methylphenylhydrazone-3-methylidene-9-ethylcarbazole, methylphenylhydrazone-4-methylidene-N,N'-diethylaniline, and the like. These charge transfer substances may be used alone or in a mixture of two or more. The optimal charge transfer material will vary depending on the disazo pigment used. For unknown reasons, certain disazo pigments provide the most suitable electrophotographic photoreceptors when combined with certain charge transport materials. In any of the photoreceptors obtained as described above, an adhesive layer or a barrier layer may be provided between the conductive support and the photosensitive layer, if necessary. Suitable materials for these layers include polyamide, nitrocellulose, aluminum oxide, and the like, and the film thickness is preferably 1 μm or less. To perform copying using the photoreceptor of the present invention, the surface of the photosensitive layer is charged, exposed, and then developed.
If necessary, this can be achieved by transferring to paper or the like. The photoreceptor of the present invention has excellent advantages such as high sensitivity on the short wavelength side and high flexibility. Examples are shown below. Example 1 2 parts by weight of disazo pigment No. 5 and 98 parts by weight of tetrahydrofuran were pulverized and mixed in a ball mill, and the resulting dispersion was applied onto an aluminum-deposited polyester film with a doctor blade and air-dried to a thickness of 1 μm. A charge generation layer was formed. On the other hand, 9-
(4-diethylaminostyryl)anthracene 2
Part by weight, polycarbonate resin [manufactured by Teijin Co., Ltd.]
Panlite L] 2 parts by weight of tetrahydrofuran 16
Dissolve it in parts by weight, apply it on the charge generation layer with a doctor blade, dry it for 10 minutes at 120°C, and adjust the thickness.
A charge transfer layer having a thickness of 11 μm was formed to obtain the laminated photoreceptor shown in FIG. Next, a -6KV corona discharge was applied to the photosensitive layer surface of this photoreceptor using a commercially available electrostatic copying paper tester for 20 seconds to negatively charge it, and then it was left in a dark place for 20 seconds. ), then irradiate the photosensitive layer with light from a tungsten lamp so that the surface potential is 20 lux, find the time (seconds) until the surface potential becomes 1/2 of Vpo, and calculate the halving exposure time. It was set as T1/2 (seconds). The result was {Vpo-1090 volts, T1/21.6 seconds}. Furthermore, the photosensitive layer was charged negatively and left in a dark place to measure Vpo (volts), and then the photosensitive layer was irradiated with light that passed through a filter that cut out light of 620 nm or more, and the surface potential was 1/2 of V′po. The time (seconds) required for this to occur was determined as the half-reduction exposure time T1/2 (seconds). The result {V′po−1090 volts, T′1/21.7 seconds}
It was hot. T′1/2/T1/2=1.06, indicating that the sensitivity on the short wavelength side is excellent. Furthermore, this photoreceptor was used in a commercially available copying machine (P-500 manufactured by Ricoh Co., Ltd.) to make copies, with black original parts (Kodatsu gray scale 1.6) and red original parts (Kodatsu color control patch, brimmer imprint). The image density of the image (red) was measured using a Macbeth densitometer. Black original portion 1.1 Red original portion 0.9 Comparative example Lamination was performed in exactly the same manner as in Example 1, except that Chlordiane Blue described in JP-A-47-37543 was used instead of disazo pigment No. 5 of Example 1. A type photoreceptor was obtained. Next, using this photoreceptor, T′1/2/T
I asked for 1/2. T'1/2/T1/2=1.83 Image density was also determined in the same manner as in Example 1. Black image area: 1.1 Red image area: 0.4 From this, it is understood that by using the charge generating substance of the present invention in an electrophotographic photoreceptor, excellent reproducibility is achieved even in the red image area. Example 2 1 part by weight of No. 1 disazo pigment and 66 parts by weight of a 0.5 weight percent tetrahydrofuran solution of polyester resin (Pylon 200 manufactured by Toyobo Co., Ltd.) were ground and mixed in a ball mill, and the resulting dispersion was mixed with aluminum. It was applied onto the vapor-deposited polyester film using a doctor blade and dried at 80° C. for 2 minutes to form a charge generation layer with a thickness of 0.7 μm. Separately, 2 parts by weight of 1,1-bis(4-dibenzylaminophenyl)propane and 2 parts by weight of poker carbonate resin (Panlite K-1300 manufactured by Teijin Co., Ltd.) were dissolved in 16 parts by weight of tetrahydrofuran. Apply it on the charge generation layer with a doctor blade,
The mixture was dried at 120° C. for 10 minutes to form a charge transfer layer with a thickness of 13 μm, thereby obtaining the laminated photoreceptor shown in FIG. Next, T'1/2/T1/2 was determined in exactly the same manner as in Example 1. T′1/2/T1/2=1.03 Examples 3 to 5 The same procedure as in Example 2 was used except that disazo pigments with the numbers shown in Table 1 below were used instead of disazo pigment No. 1. The photoreceptor shown in FIG. 1 was prepared and T'1/2/T1/2 was determined using the same method, and the results shown in Table 1 were obtained.
【表】
実施例 ６
No.４のジスアゾ顔料２重量部及びテトラヒドロ
フラン70重量部をボールミル中で粉砕混合し、得
られた分散液を、アルミニウム蒸着ポリエステル
フイルム上にドクターブレードで塗布し、自然乾
燥して厚さ1.5μの電荷発生層を形成せしめた。
一方、１−フエニル−３−（４−ジエチルアミ
ノスチリル）−５−（４−ジエチルアミノフエニ
ル）ピラゾリン２重量部及びポリスチレン（三井
東圧化学(株)製トーボレツクス）８重量部をテトラ
ヒドロフラン17重量部に溶解し、これを前記電荷
発生層上にドクターブレードで塗布し、120℃で
10分間乾燥して厚さ16μの電荷移動層を形成せし
め第１図の積層型感光体を得た。次いで、実施例
１と全く同様にしてT′1/2／Ｔ1/2を求めた。
T′1/2／Ｔ1/2＝1.08
実施例 ７〜10
実施例６においてNo.４のジスアゾ顔料のかわり
に下記表−２に示す番号のジスアゾ顔料を用いた
他は全く同様に操作し第１図の感光体を作成し、
同じ方法でT′1/2／Ｔ1/2を求め表−２の結果を
得た。[Table] Example 6 2 parts by weight of No. 4 disazo pigment and 70 parts by weight of tetrahydrofuran were pulverized and mixed in a ball mill, and the resulting dispersion was applied onto an aluminum-deposited polyester film with a doctor blade and air-dried. A charge generation layer having a thickness of 1.5 μm was formed. On the other hand, 2 parts by weight of 1-phenyl-3-(4-diethylaminostyryl)-5-(4-diethylaminophenyl)pyrazoline and 8 parts by weight of polystyrene (Toborex, manufactured by Mitsui Toatsu Chemical Co., Ltd.) were added to 17 parts by weight of tetrahydrofuran. Dissolve and apply this onto the charge generation layer using a doctor blade, and heat at 120°C.
The mixture was dried for 10 minutes to form a charge transfer layer with a thickness of 16 μm, thereby obtaining the laminated photoreceptor shown in FIG. Next, T'1/2/T1/2 was determined in exactly the same manner as in Example 1. T′1/2/T1/2=1.08 Examples 7 to 10 The same procedure as in Example 6 was used except that disazo pigments with the numbers shown in Table 2 below were used instead of disazo pigment No. 4. Create the photoconductor shown in Figure 1,
T'1/2/T1/2 was determined using the same method and the results shown in Table 2 were obtained.
【表】
実施例 11
No.13のジスアゾ顔料２重量部及びテトラヒドロ
フラン98重量部をボールミル中で粉砕混合し、得
られた分散液をアルミニウム蒸着ポリエステルフ
イルム上にドクターブレードで塗布し、自然乾燥
して厚さ1μの電荷発生層を形成せしめた。
一方、メチルフエニルヒドラゾン−３−メチリ
デン−９−エチルカルバゾール２重量部、ポリ−
Ｎ−ビニルカルバゾール（BASF社製ルビカンＭ
−170）１重量部、ポリエステル樹脂（実施例２
と同じ）１重量部をテトラヒドロフラン18重量部
に溶解しこれを前記電荷担体発生層上にドクター
ブレードで塗布し、120℃で10分間乾燥して厚さ
16μの電荷移動層を形成せしめ、第１図の積層型
感光体を得た。
次いで実施例１と全く同様にしてT′1/2／Ｔ1/
２を求めた。
T′1/2／Ｔ1/2＝1.07
実施例 12〜15
実施例11においてNo.13のジスアゾ顔料のかわり
に下記表−３に示す番号のジスアゾ顔料を用いた
他は全く同様に操作し、第１図の感光体を作成
し、同じ方法でT′1/2／Ｔ1/2を求め、表−３の
結果を得た。[Table] Example 11 2 parts by weight of disazo pigment No. 13 and 98 parts by weight of tetrahydrofuran were pulverized and mixed in a ball mill, the resulting dispersion was applied onto an aluminum-deposited polyester film with a doctor blade, and air-dried. A charge generation layer with a thickness of 1 μm was formed. On the other hand, 2 parts by weight of methylphenylhydrazone-3-methylidene-9-ethylcarbazole, poly-
N-vinylcarbazole (BASF Rubican M)
-170) 1 part by weight, polyester resin (Example 2
1 part by weight (same as ) in 18 parts by weight of tetrahydrofuran, coated on the charge carrier generation layer with a doctor blade, dried at 120°C for 10 minutes, and thickened.
A charge transfer layer of 16μ was formed to obtain a laminated photoreceptor as shown in FIG. Then, in exactly the same manner as in Example 1, T′1/2/T1/
I asked for 2. T′1/2/T1/2=1.07 Examples 12 to 15 The same procedure as in Example 11 was used except that disazo pigments with numbers shown in Table 3 below were used instead of disazo pigment No. 13. The photoreceptor shown in FIG. 1 was prepared and T'1/2/T1/2 was determined using the same method, and the results shown in Table 3 were obtained.
【表】
実施例 16
ポリエステル樹脂（実施例２と同じ）10重量
部、２，５−ビス（４−ジエチルアミノフエニ
ル）−１，３，４−オキサジアゾール10重量部、
No.３のジスアゾ顔料２重量部及びテトラヒドロフ
ラン108重量部をボールミル中で粉砕混合し、得
られた分散液を、アルミニウムを蒸着したポリエ
ステルフイルム上にドクターブレードを用いて塗
布し、120℃で10分間乾燥して厚さ21μの感光層
を持つ第２図の形態の感光体を作成した。以下こ
の感光体について＋6KVのコロナ放電を用いた
他は実施例１と同じ測定を行ない、T′1/2／Ｔ1/
２を求めた。
T′1/2／Ｔ1/2＝1.02
実施例 17〜20
実施例16においてNo.３のジスアゾ顔料の代りに
下記表−４に示す番号のジスアゾ顔料を用いた他
は全く同様に操作し第２図の感光体を作成し同じ
方法でT′1/2／Ｔ1/2を求め表−４の結果を得た。[Table] Example 16 10 parts by weight of polyester resin (same as Example 2), 10 parts by weight of 2,5-bis(4-diethylaminophenyl)-1,3,4-oxadiazole,
2 parts by weight of disazo pigment No. 3 and 108 parts by weight of tetrahydrofuran were pulverized and mixed in a ball mill, and the resulting dispersion was applied onto a polyester film coated with aluminum using a doctor blade, and heated at 120°C for 10 minutes. A photoreceptor having a dry photoreceptor layer having a thickness of 21 μm as shown in FIG. 2 was prepared. Below, the same measurements as in Example 1 were carried out on this photoreceptor except that +6KV corona discharge was used, and T'1/2/T1/
I asked for 2. T'1/2/T1/2=1.02 Examples 17 to 20 The same procedure as in Example 16 was used except that disazo pigments with numbers shown in Table 4 below were used instead of disazo pigment No. 3. The photoreceptor shown in Figure 2 was prepared and T'1/2/T1/2 was determined using the same method, and the results shown in Table 4 were obtained.
【表】
実施例 21
ポリエステル樹脂（実施例２と同じ）１重量
部、No.10のジスアゾ顔料１重量部及びテトラヒド
ロフラン2.6重量部をボールミル中で粉砕混合し、
得られた分散液を、アルミニウム蒸着したポリエ
ステルフイルム上にドクターブレードを用いて塗
布し、100℃で10分間乾燥して厚さ7μの感光層を
持つた第３図の形態の感光体を得た。
以下この感光体について＋6KVのコロナ放電
を用いた他は実施例１と同じ測定を行ない、
T′1/2／Ｔ1/2を求めた。
T′1/2／Ｔ1/2＝1.10
実施例 22〜25
実施例21においてNo.10のジスアゾ顔料の代りに
下記表−５に示す番号のジスアゾ顔料を用いた他
は全く同様に操作し第３図の感光体を作成し同じ
方法でT′1/2／Ｔ1/2を求め表−５の結果を得た。[Table] Example 21 1 part by weight of polyester resin (same as in Example 2), 1 part by weight of No. 10 disazo pigment, and 2.6 parts by weight of tetrahydrofuran were pulverized and mixed in a ball mill.
The resulting dispersion was applied onto a polyester film coated with aluminum using a doctor blade, and dried at 100°C for 10 minutes to obtain a photoreceptor with a photosensitive layer having a thickness of 7 μm as shown in Figure 3. . Below, the same measurements as in Example 1 were carried out on this photoreceptor except that +6KV corona discharge was used.
T′1/2/T1/2 was calculated. T′1/2/T1/2=1.10 Examples 22 to 25 The same procedure as in Example 21 was used except that disazo pigments with numbers shown in Table 5 below were used instead of disazo pigment No. 10. The photoreceptor shown in Figure 3 was prepared and T'1/2/T1/2 was determined using the same method, and the results shown in Table 5 were obtained.
第１〜３図はそれぞれ本発明感光体の説明図で
ある。
１……導電性支持体、２，２′，２″……感光
層、３……ジスアゾ顔料、４……電荷移動媒体、
５……電荷発生層、６……電荷移動層。
1 to 3 are explanatory diagrams of the photoreceptor of the present invention, respectively. 1... Conductive support, 2, 2', 2''... Photosensitive layer, 3... Disazo pigment, 4... Charge transfer medium,
5... Charge generation layer, 6... Charge transfer layer.
Claims (1)
体、Ar1は芳香環、複素還又はそれらの置換体、
Ar2およびAr3は芳香環またはそれらの置換体、
R1およびR3は水素、低級アルキル基、フエニル
基またはその置換体、R2は低級アルキル基、カ
ルボキシル基またはそのエステルを表わす）を表
わす。〕で示されるジスアゾ顔料を有効成分とし
て含有する感光層を有することを特徴とする電子
写真用感光体。[Claims] 1. On a conductive support, the following general formula [However, A is [Formula] [Formula] or [Formula] (where X is an aromatic ring, a heterocycle, or a substituent thereof, Ar 1 is an aromatic ring, a heterocycle, or a substituent thereof,
Ar 2 and Ar 3 are aromatic rings or substituted products thereof,
R 1 and R 3 represent hydrogen, a lower alkyl group, a phenyl group, or a substituted product thereof, and R 2 represents a lower alkyl group, a carboxyl group, or an ester thereof. 1. A photoreceptor for electrophotography, comprising a photosensitive layer containing a disazo pigment as an active ingredient.
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16701680A JPS5789762A (en) | 1980-11-26 | 1980-11-26 | Electrophotographic receptor |
| US06/218,383 US4349616A (en) | 1979-12-28 | 1980-12-19 | Disazo pigment containing electrophotographic element |
| CA000367557A CA1165611A (en) | 1979-12-28 | 1980-12-24 | Electrophotographic element with photosensitive layer containing a disazo pigment |
| FR8027551A FR2476336B1 (en) | 1979-12-28 | 1980-12-24 | ELECTROPHOTOGRAPHIC ELEMENT |
| DE19803049303 DE3049303A1 (en) | 1979-12-28 | 1980-12-29 | ELECTROPHOTOGRAPHIC ELEMENT |
| GB8041347A GB2067776B (en) | 1979-12-28 | 1980-12-29 | Electrophotographic elements |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16701680A JPS5789762A (en) | 1980-11-26 | 1980-11-26 | Electrophotographic receptor |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5789762A JPS5789762A (en) | 1982-06-04 |
| JPS6318741B2 true JPS6318741B2 (en) | 1988-04-20 |
Family
ID=15841817
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16701680A Granted JPS5789762A (en) | 1979-12-28 | 1980-11-26 | Electrophotographic receptor |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5789762A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0463527U (en) * | 1990-10-15 | 1992-05-29 | ||
| JPH0574309A (en) * | 1991-08-01 | 1993-03-26 | Kojundo Chem Lab Co Ltd | Circuit breaker |
-
1980
- 1980-11-26 JP JP16701680A patent/JPS5789762A/en active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0463527U (en) * | 1990-10-15 | 1992-05-29 | ||
| JPH0574309A (en) * | 1991-08-01 | 1993-03-26 | Kojundo Chem Lab Co Ltd | Circuit breaker |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5789762A (en) | 1982-06-04 |
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