JPS6261258B2 - - Google Patents
Info
- Publication number
- JPS6261258B2 JPS6261258B2 JP8925581A JP8925581A JPS6261258B2 JP S6261258 B2 JPS6261258 B2 JP S6261258B2 JP 8925581 A JP8925581 A JP 8925581A JP 8925581 A JP8925581 A JP 8925581A JP S6261258 B2 JPS6261258 B2 JP S6261258B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- resin
- charge
- layer
- ring
- 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 34
- 239000000049 pigment Substances 0.000 claims description 19
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 17
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 4
- -1 t-octyl group Chemical group 0.000 description 113
- 239000010410 layer Substances 0.000 description 57
- 239000011230 binding agent Substances 0.000 description 16
- 239000000463 material Substances 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 229920005989 resin Polymers 0.000 description 10
- 239000011347 resin Substances 0.000 description 10
- 239000011248 coating agent Substances 0.000 description 9
- 238000000576 coating method Methods 0.000 description 9
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 238000001035 drying Methods 0.000 description 6
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 6
- 230000035945 sensitivity Effects 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 229920001225 polyester resin Polymers 0.000 description 5
- 239000004645 polyester resin Substances 0.000 description 5
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 125000006267 biphenyl group Chemical group 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000005018 casein Substances 0.000 description 4
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 4
- 235000021240 caseins Nutrition 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 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 4
- 229920000515 polycarbonate Polymers 0.000 description 4
- 239000004417 polycarbonate Substances 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 229920000178 Acrylic resin Polymers 0.000 description 3
- 239000004925 Acrylic resin Substances 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 239000012790 adhesive layer Substances 0.000 description 3
- 150000008366 benzophenones Chemical group 0.000 description 3
- 125000004799 bromophenyl group Chemical group 0.000 description 3
- 125000000068 chlorophenyl group Chemical group 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 125000004802 cyanophenyl group Chemical group 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 125000004188 dichlorophenyl group Chemical group 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 239000003822 epoxy resin Substances 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 3
- 125000006501 nitrophenyl group Chemical group 0.000 description 3
- 229920000647 polyepoxide Polymers 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 239000011669 selenium Substances 0.000 description 3
- 229910052711 selenium Inorganic materials 0.000 description 3
- 230000001235 sensitizing effect Effects 0.000 description 3
- 125000003944 tolyl group Chemical group 0.000 description 3
- 125000005023 xylyl group Chemical group 0.000 description 3
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 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
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- 229920002799 BoPET Polymers 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000005041 Mylar™ Substances 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229920000180 alkyd Polymers 0.000 description 2
- 229910052980 cadmium sulfide Inorganic materials 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- UOCJDOLVGGIYIQ-PBFPGSCMSA-N cefatrizine Chemical group S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)[C@H](N)C=2C=CC(O)=CC=2)CC=1CSC=1C=NNN=1 UOCJDOLVGGIYIQ-PBFPGSCMSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 125000004803 chlorobenzyl group Chemical group 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group 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
- 125000006286 dichlorobenzyl group Chemical group 0.000 description 2
- 125000006182 dimethyl benzyl group Chemical group 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000000113 methacrylic resin Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000006178 methyl benzyl group Chemical group 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000001400 nonyl 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])[H] 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000005011 phenolic resin Substances 0.000 description 2
- 229920002382 photo conductive polymer Polymers 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 2
- 229920005668 polycarbonate resin Polymers 0.000 description 2
- 239000004431 polycarbonate resin Substances 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 150000003219 pyrazolines Chemical class 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 125000004079 stearyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- AIGNCQCMONAWOL-UHFFFAOYSA-N 1,3-benzoselenazole Chemical group C1=CC=C2[se]C=NC2=C1 AIGNCQCMONAWOL-UHFFFAOYSA-N 0.000 description 1
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 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
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 1
- LFKNYYQRWMMFSM-UHFFFAOYSA-N 1-ethyl-9h-carbazole;formaldehyde Chemical compound O=C.N1C2=CC=CC=C2C2=C1C(CC)=CC=C2 LFKNYYQRWMMFSM-UHFFFAOYSA-N 0.000 description 1
- USYCQABRSUEURP-UHFFFAOYSA-N 1h-benzo[f]benzimidazole Chemical group C1=CC=C2C=C(NC=N3)C3=CC2=C1 USYCQABRSUEURP-UHFFFAOYSA-N 0.000 description 1
- VEUMBMHMMCOFAG-UHFFFAOYSA-N 2,3-dihydrooxadiazole Chemical compound N1NC=CO1 VEUMBMHMMCOFAG-UHFFFAOYSA-N 0.000 description 1
- JOERSAVCLPYNIZ-UHFFFAOYSA-N 2,4,5,7-tetranitrofluoren-9-one Chemical compound O=C1C2=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C2C2=C1C=C([N+](=O)[O-])C=C2[N+]([O-])=O JOERSAVCLPYNIZ-UHFFFAOYSA-N 0.000 description 1
- FVNMKGQIOLSWHJ-UHFFFAOYSA-N 2,4,5,7-tetranitroxanthen-9-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)C3=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C3OC2=C1[N+]([O-])=O FVNMKGQIOLSWHJ-UHFFFAOYSA-N 0.000 description 1
- PDEJYRZFAJILSQ-UHFFFAOYSA-N 2,4,7-trinitro-9h-fluorene Chemical compound [O-][N+](=O)C1=CC([N+]([O-])=O)=C2C3=CC=C([N+](=O)[O-])C=C3CC2=C1 PDEJYRZFAJILSQ-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
- AJRKAOOOTRIGSZ-UHFFFAOYSA-N 2-(2,3,4-trinitro-1-oxo-2h-fluoren-9-ylidene)propanedinitrile Chemical compound C1=CC=C2C(=C(C#N)C#N)C(C(=O)C(C(=C3[N+]([O-])=O)[N+]([O-])=O)[N+](=O)[O-])=C3C2=C1 AJRKAOOOTRIGSZ-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- FLCWJWNCSHIREG-UHFFFAOYSA-N 2-(diethylamino)benzaldehyde Chemical compound CCN(CC)C1=CC=CC=C1C=O FLCWJWNCSHIREG-UHFFFAOYSA-N 0.000 description 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- 125000006197 2-benzoyl ethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(=O)C([H])([H])C([H])([H])* 0.000 description 1
- LAXBNTIAOJWAOP-UHFFFAOYSA-N 2-chlorobiphenyl Chemical compound ClC1=CC=CC=C1C1=CC=CC=C1 LAXBNTIAOJWAOP-UHFFFAOYSA-N 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- LWFUFLREGJMOIZ-UHFFFAOYSA-N 3,5-dinitrosalicylic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O LWFUFLREGJMOIZ-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
- 229910001369 Brass Inorganic materials 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 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
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 241000519995 Stachys sylvatica Species 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 229920002433 Vinyl chloride-vinyl acetate copolymer Polymers 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 125000005577 anthracene group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000005110 aryl thio group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000006149 azo coupling reaction Methods 0.000 description 1
- 238000000498 ball milling Methods 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- AMTXUWGBSGZXCJ-UHFFFAOYSA-N benzo[e][1,3]benzoselenazole Chemical group C1=CC=C2C(N=C[se]3)=C3C=CC2=C1 AMTXUWGBSGZXCJ-UHFFFAOYSA-N 0.000 description 1
- KXNQKOAQSGJCQU-UHFFFAOYSA-N benzo[e][1,3]benzothiazole Chemical group C1=CC=C2C(N=CS3)=C3C=CC2=C1 KXNQKOAQSGJCQU-UHFFFAOYSA-N 0.000 description 1
- WMUIZUWOEIQJEH-UHFFFAOYSA-N benzo[e][1,3]benzoxazole Chemical group C1=CC=C2C(N=CO3)=C3C=CC2=C1 WMUIZUWOEIQJEH-UHFFFAOYSA-N 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- HSUIVCLOAAJSRE-UHFFFAOYSA-N bis(2-methoxyethyl) benzene-1,2-dicarboxylate Chemical compound COCCOC(=O)C1=CC=CC=C1C(=O)OCCOC HSUIVCLOAAJSRE-UHFFFAOYSA-N 0.000 description 1
- 239000010951 brass Substances 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000012461 cellulose resin Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 229920006026 co-polymeric resin Polymers 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 125000000332 coumarinyl group Chemical group O1C(=O)C(=CC2=CC=CC=C12)* 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 125000005447 octyloxy 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])O* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 229920006287 phenoxy resin Polymers 0.000 description 1
- 239000013034 phenoxy resin Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 description 1
- 150000004291 polyenes Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 229920002717 polyvinylpyridine Polymers 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- RCYFOPUXRMOLQM-UHFFFAOYSA-N pyrene-1-carbaldehyde Chemical compound C1=C2C(C=O)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 RCYFOPUXRMOLQM-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 229930187593 rose bengal Natural products 0.000 description 1
- AZJPTIGZZTZIDR-UHFFFAOYSA-L rose bengal Chemical compound [K+].[K+].[O-]C(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C1=C2C=C(I)C(=O)C(I)=C2OC2=C(I)C([O-])=C(I)C=C21 AZJPTIGZZTZIDR-UHFFFAOYSA-L 0.000 description 1
- 229940081623 rose bengal Drugs 0.000 description 1
- STRXNPAVPKGJQR-UHFFFAOYSA-N rose bengal A Natural products O1C(=O)C(C(=CC=C2Cl)Cl)=C2C21C1=CC(I)=C(O)C(I)=C1OC1=C(I)C(O)=C(I)C=C21 STRXNPAVPKGJQR-UHFFFAOYSA-N 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- NLDYACGHTUPAQU-UHFFFAOYSA-N tetracyanoethylene Chemical group N#CC(C#N)=C(C#N)C#N NLDYACGHTUPAQU-UHFFFAOYSA-N 0.000 description 1
- PCCVSPMFGIFTHU-UHFFFAOYSA-N tetracyanoquinodimethane Chemical compound N#CC(C#N)=C1C=CC(=C(C#N)C#N)C=C1 PCCVSPMFGIFTHU-UHFFFAOYSA-N 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000006163 transport media Substances 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-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
- 238000001771 vacuum deposition Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
- G03G5/0664—Dyes
- G03G5/0675—Azo dyes
- G03G5/0687—Trisazo dyes
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Photoreceptors In Electrophotography (AREA)
Description
本発明は、改良された電子写真感光体に関する
もので、特に電荷発生層と電荷輸送層を有する感
光層の電荷発生物質として適したビスアゾ顔料を
用いた電子写真感光体に関するものである。
従来、電子写真感光体で用いる件導電性材料と
して、セレン、硫化カドミウム、酸化亜鉛などの
無機光導電性材料が知られている。これらの光導
電性材料は、数多くの利点、例えば暗所で適当な
電位に帯電できること、暗所で電荷の逸散が少な
いことあるいは光照射によつて速かに電荷を逸散
できるなどの利点をもつている反面、各種の欠点
を有している。例えば、セレン系感光体では、温
度、湿度、ごみ、圧力などの要因で容易に結晶化
が進み、特に雰囲気温度が40℃を越えると結晶化
が著しくなり、帯電性の低下や画像に白い斑点が
発生するといつた欠点がある。また、セレン系感
光体や硫化カドミウム系感光体は、多湿下の経時
の使用において安定した耐久性が得られない欠点
がある。
また、酸化亜鉛系感光体は、ローズベンガルに
代表される増感色素による増感効果を必要として
いるが、この様な増感色素がコロナ帯電による通
電劣化や露光光による光退色を生じるため長期に
亘つて安定した画像を与えることができない欠点
を有している。
一方、ポリビニルカルバゾールをはじめとする
各種の有機光導電性ポリマーが提案されて来た
が、これらのポリマーは、前述の無機系光導電材
料に較べ成膜性、軽量性などの点で優れているに
もかかわらず、今日までその実用化が困難であつ
たのは、感度および耐久性の点で無機系光導電材
料に較べ劣つているためであつた。
この様なことから、近年感光層を電荷発生層と
電荷輸送層に機能分離させた積層構造体が提案さ
れた。この積層構造を感光層とした電子写真感光
体は、可視光に対する感度、電荷保持力、表面強
度などの点で改善できる様になつた。この様な電
子写真感光体は、例えば特開昭49−105537号、特
開昭51−90827号、米国特許第3484237号、米国特
許第3871882号、各公報などに開示されている。
しかし、この様な電子写真感光体でも、未だに
十分に満足できる感度が得られず、しかも繰り返
し帯電および露光を行なつた際には表面電位の変
動、特に繰り返し露光および帯電を行なつた時
に、明部電位の増加と暗部電位の低下を惹き起こ
してしまうなどの不利がある。
本発明の目的は、前述の欠点若しくは不利を解
消しうる新規な電子写真感光体を提供することに
ある。
本発明の別の目的は、新規な有機光導電性材料
を提供することにある。
本発明の別の目的は、前述の積層構造体を有す
る感光層の電荷発生物質として用いるに適したビ
スアズ顔料を提供することにある。
本発明の別の目的は、新規な電荷発生物質を含
有させた電荷発生層を有する感光層の提供にあ
る。
本発明の別の目的は、感度および耐久性が改善
された電子写真感光体の提供にある。
本発明は、下記一般式〔〕で示されるビスア
ゾ顔料を含有する感光層、特にこのビスアゾ顔料
を含有する電荷発生層を有する電子写真感光体に
特徴を有している。
一般式〔〕
式中、Rは置換されてもよいアルキル基(例え
ば、メチル基、エチル基、プロピル基、iso−プ
ロピル基、ブチル基、sec−ブチル基、t−ブチ
ル基、アミル基、t−アミル基、ヘキシル基、シ
クロヘキシル基、オクチル基、t−オクチル基、
2−エチルヘキシル基、ノニル基、オクタデシル
基、ベンジル基、クロロベンジル基、ジクロロベ
ンジル基、メチルベンジル基、ジメチルベンジル
基、2−フエニルエチル基、3−フエニルプロピ
ル基、α−ナフチルメチル基、β−ナフチルメチ
ル基、2−α−ナフチルエチル基など)若しくは
アリール基(例えば、フエニル基、トリル基、キ
シリル基、ビフエニル基、クロロフエニル基、ジ
クロロフエニル基、トソクロロフエニル基、ブロ
モフエニル基、ジブロモフエニル基、トソブロモ
フエニル基、メトキシフエニル基、エトキシフエ
ニル基、ブトキシフエニル基、フエノキシフエニ
ル基、ニトロフエニル基、シアノフエニル基、ヒ
ドロキシフエニル基、カルボキシフエニル基、
N・N−ジメチルアミノフエニル基、N・N−ジ
エチルアミノフエニル基、N・N−ジベンジルア
ミノフエニル基、アセチルフエニル基、ベンゾイ
ルフエニル基、メチルチオフエニル基、エチルチ
オフエニル基、メルカプトフエニル基、α−ナフ
チル基、β−ナフチル基など)を示す。
前記A1およびA2は、置換されてもよい2価の
複素環基を示し、好ましい複素環としては、ベン
ゾイミダゾール環、ナフトイミダゾール環、ベン
ゾオキサゾール環、イソベンゾオキサゾール環、
ナフトオキサゾール環、ベンゾチアゾール環、ナ
フトチアゾール環、ベンゾセレナゾール環、ナフ
トセレナゾール環、インドリン環、インドール
環、キノリン環、イソキノリン環、ベンゾフラン
環、ジベンゾフラン環、クマリン環、カルバゾー
ル環、フエノチアジン環などの様な少なくとも1
つの縮合ベンゼン環若しくは縮合ナフタレン環を
有する複素環を挙げることができる。これらの複
素環に置換しうる原子若しくは基としては、例え
ばハロゲン原子(例えば塩素原子、臭素原子、フ
ツ素原子など)、アルキル基(例えば、メチル
基、エチル基、プロピル基、ブチル基、t−ブチ
ル基、オクチル基、t−オクチル基など)、置換
アルキル基(例えば、ベンジル基、2−フエニル
エチル基、2−ヒドロキシエチル基、3−ヒドロ
キシプロピル基、2−カルボキシエチル基、3−
カルボキシプロピル基、2−スルホエチル基な
ど)、アルコキシ基(例えば、メトキシ基、エト
キシ基、ブトキシ基、オクチルオキシ基など)、
置換若しくは非置換アリールオキシ基(例えば、
フエノキシ基、クロロフエノキシ基、ジクロロフ
エノキシ基、トリクロロフエノキシ基、ブロモフ
エノキシ基、ジブロモフエノキシ基、メチルフエ
ノキシ基、エチルフエノキシ基など)、置換若し
くは非置換アリールチオ基(例えば、フエニルチ
オ基、トリルチオ基、キシリルチオ基、クロロフ
エニルチオ基、ジクロロフエニルチオ基、ブロモ
フエニルチオ基、α−ナフチルチオ基、β−ナフ
チルチオ基など)、置換若しくは非置換アシル基
(例えば、アセチル基、プロピオニル基、ベンゾ
イル基、メチルベンゾイル基など)、置換アミノ
基(例えば、N・N−ジメチルアミノ基、N・N
−ジエチルアミノ基、N・N−ジプロピルアミノ
基、N・N−フエニルアミノ基、N・N−ベンジ
ルアミノ基、N−エチル−N−フエニルアミノ基
など)、シアノ基、ニトロ基、ヒドロキシ基、ス
ルホン基、カルボキシル基などを挙げることがで
きる。また、nおよびmは、0、1または2であ
る。A1およびA2は、同一であつてもよく、ある
いは異なつていてもよい。
前記Cpは、カプラー残基を示すが、好ましい
カプラー残基を下記に示す。
式中、Xはベンゼン環と縮合してナフタレン
環、アンスラセン環などの多環式芳香族炭化水素
環またはベンゼン環と縮合してカルバゾール環、
ジベンゾフラン環などの複素環を形成するに必要
な原子群を示す。Yは水素原子、
The present invention relates to an improved electrophotographic photoreceptor, and more particularly to an electrophotographic photoreceptor using a bisazo pigment suitable as a charge generation material in a photosensitive layer having a charge generation layer and a charge transport layer. Conventionally, inorganic photoconductive materials such as selenium, cadmium sulfide, and zinc oxide are known as conductive materials used in electrophotographic photoreceptors. These photoconductive materials have a number of advantages, such as being able to be charged to an appropriate potential in the dark, having little charge dissipation in the dark, or quickly dissipating the charge when irradiated with light. However, it also has various drawbacks. For example, selenium-based photoreceptors easily crystallize due to factors such as temperature, humidity, dust, and pressure. Especially when the ambient temperature exceeds 40°C, crystallization becomes significant, resulting in decreased charging performance and white spots on images. There is a drawback when this occurs. Furthermore, selenium-based photoreceptors and cadmium sulfide-based photoreceptors have the disadvantage that stable durability cannot be obtained when used over time under high humidity. In addition, zinc oxide photoreceptors require the sensitizing effect of sensitizing dyes such as rose bengal, but such sensitizing dyes cause deterioration due to current conduction due to corona charging and photobleaching due to exposure light, so it may take a long time. It has the disadvantage that it cannot provide a stable image over a long period of time. On the other hand, various organic photoconductive polymers including polyvinylcarbazole have been proposed, but these polymers are superior in terms of film formability and lightness compared to the inorganic photoconductive materials mentioned above. Nevertheless, it has been difficult to put them into practical use until now because they are inferior to inorganic photoconductive materials in terms of sensitivity and durability. For these reasons, a laminated structure in which the photosensitive layer is functionally separated into a charge generation layer and a charge transport layer has been proposed in recent years. Electrophotographic photoreceptors using this laminated structure as a photosensitive layer can now be improved in terms of sensitivity to visible light, charge retention, surface strength, and the like. Such electrophotographic photoreceptors are disclosed in, for example, Japanese Patent Application Laid-open Nos. 49-105537, 51-90827, US Pat. No. 3,484,237, US Pat. No. 3,871,882, and various publications. However, even with such an electrophotographic photoreceptor, it is still not possible to obtain a sufficiently satisfactory sensitivity, and moreover, the surface potential changes when repeatedly charged and exposed, especially when repeatedly exposed and charged. There are disadvantages such as an increase in bright area potential and a decrease in dark area potential. SUMMARY OF THE INVENTION An object of the present invention is to provide a new electrophotographic photoreceptor that can eliminate the above-mentioned drawbacks or disadvantages. Another object of the invention is to provide new organic photoconductive materials. Another object of the present invention is to provide a bis-azu pigment suitable for use as a charge generating material in a photosensitive layer having the above-mentioned layered structure. Another object of the present invention is to provide a photosensitive layer having a charge generation layer containing a novel charge generation substance. Another object of the present invention is to provide an electrophotographic photoreceptor with improved sensitivity and durability. The present invention is characterized by an electrophotographic photoreceptor having a photosensitive layer containing a bisazo pigment represented by the following general formula [], particularly a charge generation layer containing this bisazo pigment. General formula [] In the formula, R is an optionally substituted alkyl group (e.g., methyl group, ethyl group, propyl group, iso-propyl group, butyl group, sec-butyl group, t-butyl group, amyl group, t-amyl group, hexyl group, cyclohexyl group, octyl group, t-octyl group,
2-ethylhexyl group, nonyl group, octadecyl group, benzyl group, chlorobenzyl group, dichlorobenzyl group, methylbenzyl group, dimethylbenzyl group, 2-phenylethyl group, 3-phenylpropyl group, α-naphthylmethyl group, β- naphthylmethyl group, 2-α-naphthylethyl group) or aryl group (e.g. phenyl group, tolyl group, xylyl group, biphenyl group, chlorophenyl group, dichlorophenyl group, tosochlorophenyl group, bromophenyl group, dibromophenyl group) group, tosobromophenyl group, methoxyphenyl group, ethoxyphenyl group, butoxyphenyl group, phenoxyphenyl group, nitrophenyl group, cyanophenyl group, hydroxyphenyl group, carboxyphenyl group,
N・N-dimethylaminophenyl group, N・N-diethylaminophenyl group, N・N-dibenzylaminophenyl group, acetylphenyl group, benzoylphenyl group, methylthiophenyl group, ethylthiophenyl group , mercaptophenyl group, α-naphthyl group, β-naphthyl group, etc.). The above A 1 and A 2 represent an optionally substituted divalent heterocyclic group, and preferable heterocycles include a benzimidazole ring, a naphthimidazole ring, a benzoxazole ring, an isobenzoxazole ring,
Naphthoxazole ring, benzothiazole ring, naphthothiazole ring, benzoselenazole ring, naphthoselenazole ring, indoline ring, indole ring, quinoline ring, isoquinoline ring, benzofuran ring, dibenzofuran ring, coumarin ring, carbazole ring, phenothiazine ring, etc. at least 1
Mention may be made of heterocycles having two fused benzene rings or two fused naphthalene rings. Examples of atoms or groups that can be substituted on these heterocycles include halogen atoms (e.g. chlorine atom, bromine atom, fluorine atom, etc.), alkyl groups (e.g. methyl group, ethyl group, propyl group, butyl group, t- butyl group, octyl group, t-octyl group), substituted alkyl group (e.g. benzyl group, 2-phenylethyl group, 2-hydroxyethyl group, 3-hydroxypropyl group, 2-carboxyethyl group, 3-
carboxypropyl group, 2-sulfoethyl group, etc.), alkoxy groups (e.g., methoxy group, ethoxy group, butoxy group, octyloxy group, etc.),
Substituted or unsubstituted aryloxy groups (e.g.
phenoxy group, chlorophenoxy group, dichlorophenoxy group, trichlorophenoxy group, bromophenoxy group, dibromophenoxy group, methylphenoxy group, ethylphenoxy group), substituted or unsubstituted arylthio group (e.g. phenylthio group, tolylthio group) group, xylylthio group, chlorophenylthio group, dichlorophenylthio group, bromophenylthio group, α-naphthylthio group, β-naphthylthio group), substituted or unsubstituted acyl group (such as acetyl group, propionyl group, benzoyl group) group, methylbenzoyl group, etc.), substituted amino group (e.g., N.N.-dimethylamino group, N.N.
-diethylamino group, N・N-dipropylamino group, N・N-phenylamino group, N・N-benzylamino group, N-ethyl-N-phenylamino group, etc.), cyano group, nitro group, hydroxy group, sulfone group , carboxyl group, etc. Further, n and m are 0, 1 or 2. A 1 and A 2 may be the same or different. The above Cp represents a coupler residue, and preferred coupler residues are shown below. In the formula, X is a polycyclic aromatic hydrocarbon ring such as a naphthalene ring or anthracene ring by condensing with a benzene ring, or a carbazole ring by condensing with a benzene ring,
Indicates the atomic groups necessary to form a heterocycle such as a dibenzofuran ring. Y is a hydrogen atom,
【式】
または−COOR3を示すが、R3およびR4は、水素
原子または置換されてもよいアルキル基(例え
ば、メチル基、エチル基、プロピル基、iso−プ
ロピル基、ブチル基、sec−ブチル基、t−ブチ
ル基、アミル基、t−アミル基、ヘキシル基、シ
クロヘキシル基、オクチル基、t−オクチル基、
2−エチルヘキシル基、ノニル基、オクタデシル
基、ベンジル基、クロロベンジル基、ジクロロベ
ンジル基、メチルベンジル基、ジメチルベンジル
基、2−フエニルエチル基、3−フエニルプロピ
ル基、α−ナフチルメチル基、β−ナフチルメチ
ル基、2−α−ナフチルエチル基など)若しくは
アリール基(例えば、フエニル基、トリル基、キ
シリル基、ビフエニル基、クロロフエニル基、ジ
クロロフエニル基、トリクロロフエニル基、ブロ
モフエニル基、ジブロフエニル基、トリブロモフ
エニル基、メトキシフエニル基、エトキシフエニ
ル基、ブトキシフエニル基、フエノキシフエニル
基、ニトロフエニル、シアノフエニル基、ヒドロ
キシフエニル基、カルボキシフエニル基、N・N
−ジメチルアミノフエニル基、N・N−ジエチル
アミノフエニル基、N・N−ジベンジルアミノフ
エニル基、アセチルフエニル基、ベンゾイルフエ
ニル基、メチルチオフエニル基、エチルチオフエ
ニル基、メルカプトフエニル基、α−ナフチル
基、β−ナフチル基など)を示す。但し、R3と
R4が、同時に水素原子であることはない。ま
た、−COOR3の時、R3は水素原子であることはな
い。前記R1およびR2は、置換されてもよいアル
キル基(例えば、メチル基、エチル基、プロピル
基、ブチル基、t−ブチル基、ヘキシル基、シク
ロヘキシル基、オクチル基、t−オクチル基、2
−エチルヘキシル基、ベンジル基、2−フエニル
エチル基、α−ナフチルメチル基、β−ナフチル
メチル基、メトキシメチル基、エトキシメチル
基、2−メトキシエチル基、2−エトキシエチル
基、2−ヒドロキシエチル基、2−カルボキシエ
チル基、2−ヒドロキシプロピル基、3−ヒドロ
キシプロピル基、3−スルホプロピル基、フエノ
キシメチル基、2−フエノキシエチル基、3−フ
エノキシプロピル基、4−フエノキシブチル基、
2−シアノエチル基、3−シアノプロピル基、ア
セチルメチル基、2−アセチルエチル基、3−ア
セチルプロピル基、ベンゾイルメチル基、2−ベ
ンゾイルエチル基、3−ベンゾイルプロピル基、
メトキシメトキシメチル基、2−メトキシメトキ
シエチル基、3−メトキシメトキシプロピル基、
N・N−ジメチルアミノメチル基、N・N−ジエ
チルアミノメチル基、N・N−ジベンジルアミノ
メチル基、2−N・N−ジエチルアミノエチル
基、2−N・N−ジベンジルアミノエチル基、3
−N・N−ジエチルアミノプロピル基、3−N・
N−ジフエニルアミノプロピル基、3−メルカル
トプロピル基、4−メルカプトブチル基、2−ク
ロロエチル基、3−クロロプロピル基、4−クロ
ロブチル基、3−クロロブチル基、フエニルチオ
メチル基、2−フエニルチオエチル基、3−フエ
ニルチオプロピル基など)若しくはアリール基
(例えば、フエニル基、トリル基、キシリル基、
ビフエニル基、クロロフエニル基、ジクロロフエ
ニル基、トリクロロフエニル基、ブロモフエニル
基、ニトロフエニル基、シアノフエニル基、メト
キシフエニル基、エトキシフエニル基、エチルフ
エニル基、ジエチルフエニル基、プロピルフエニ
ル基、フエノキシフエニル基、フエニルチオフエ
ニル基、カルボキシフエニル基、ヒドロキシフエ
ニル基、スルホフエニル基、N・N−ジメチルア
ミノフエニル基、N・N−ジエチルアミノフエニ
ル基、N・N−ジフエニルアミノフエニル基、N
−エチル−N−メチルアミノフエニル基、アセチ
ルフエニル基、ベンゾイルフエニル基、α−ナフ
チル基、β−ナフチル基など)を示す。
前記一般式〔〕で示されるビスアゾ顔料の具
体例を下記に列挙する。
ビスアゾ顔料
これらのビスアゾ顔料は、一般式(a)に示すジア
ミン化合物を常法によりテトラゾ化した後に、カ
プラーとアルカリの存在下でジアゾカツプリング
反応を行なうか、あるいはジアミン化合物をジア
ゾ化した後、テトラゾニウム塩をホウフツ化塩ま
たは塩化亜鉛を用いて単離し、N・N−ジメチル
ホルムアミド、ジメチルスルホキシドなどの溶媒
中でピリジンなどのアルカリの存在下でカツプリ
ング反応させて容易に調製できる。一般式(a)
(式中、A1、A2、R、nおよびmは、前記と同義
語である。)
これらのビスアゾ顔料は、1種または2種以上
組合せて用いることもできる。
本発明の電子写真感光体は、前述のビスアゾ顔
料を含有させた電荷発生層を適当な支持体の上に
塗工し、この電荷発生層の上に電荷輸送層を積層
した構造の感光層を用いることによつて作成され
ることができる。この型の電子写真感光体は、適
当な支持体の上に中間層を設け、これを介して前
述のビスアゾ顔料を含む電荷発生層を形成し、そ
の上に下述の電荷輸送層を形成しても良い。この
中間層は、積層構造からなる感光層の帯電時にお
いて導電性支持体から感光層への自由電荷の注入
を阻止するとともに、感光層を導電性支持体に対
して一体的に接着保持せしめる接着層としての作
用を示す。この中間層は、酸化アルミニウムなど
の金属酸化物あるいはポリエチレン、ポリプロピ
レン、アクリル樹脂、メタクリル樹脂、塩化ビニ
ル樹脂、フエノール樹脂、エポキシ樹脂、ポリエ
ステル樹脂、アルキド樹脂、ポリカーボネート、
ポリウレタン、ポリイミド樹脂、塩化ビニリデン
樹脂、塩化ビニル−酢酸ビニル共重合体、カゼイ
ン、ゼラチン、ポリビニルアルコール、水溶性ポ
リエチレン、ニトロセルロースなどを用いること
ができる。この中間層または接着層の厚みは、
0.1μ〜5μ、好ましくは0.5〜3μが適当であ
る。
また、電荷発生層を電荷輸送層の上に設けた積
層構造とすることもでき、この場合には、適当な
表面保護層を形成させることもできる。
電荷発生層は用いる電荷発生材料の種類により
真空蒸着、スパツタリング、グロー放電ないしは
塗工等の手段によつて設けることができる。
塗工に際しては、電荷発生材料をバインダー・
フリーで設ける場合や樹脂分散液として設ける場
合や、バインダーと電荷発生材料の均一溶液とし
て設ける場合等がある。ビスアゾ顔料の分散に際
してはボールミル、アトライターなど公知の方法
を用いることができ顔料粒子が5μ以下好ましく
は2μ以下最適には0.5μ以下とすることが望ま
しい。
ジスアゾ顔料はエチレンジアミン等のアミン系
溶剤に溶かして塗布することもできる。塗布方法
はブレード、マイヤーバー、スプレー浸漬などの
通常の方法が用いられる。
電荷発生層の膜厚は5μ以下好ましくは0.01〜
1μが望ましい。電荷発生層にバインダーを用い
る場合バインダー量が多いと感度に影響するた
め、電荷発生層中に占めるバインダーの割合は80
%以下好ましくは40%以下が望ましい。
使用されるバインダーとしてはポリビニルブチ
ラール、ポリ酢酸ビニル、ポリエステル、ポリカ
ーボネート、フエノキシ樹脂、アクリル系樹脂、
ポリアクリルアミド、ポリアミド、ポリビニルピ
リジン樹脂、セルローズ系樹脂、ウレタン樹脂、
エポキシ樹脂、カゼイン、ポリビニルアルコール
などの各種樹脂類が用いられる。
電荷発生層より上層の電荷輸送層のキヤリヤー
注入を均一にするために必要があれば電荷発生層
の表面を研磨し鏡面仕上げをすることができる。
この様にして設けた電荷発生層上に電荷輸送層
を設ける。電荷輸送物が被膜形成能をもたない場
合はバインダーを適当な有機溶剤に溶かした液を
通常の方法で塗布乾燥し電荷輸送層を形成する。
電荷輸送物質としては電子輸送性物質と正孔輸送
性物質がある。
電子輸送性物質としては、クロルアニル、ブロ
モアニル、テトラシアノエチレン、テトラシアノ
キノジメタン、2・4・7−トリニトロ−9−フ
ルオレン、2・4・5・7−テトラニトロフルオ
レノン、2・4・7−トリニトロ−9−ジシアノ
メチレンフルオレノン、2・4・5・7−テトラ
ニトロキサントン、2・4・8−トリニトロチオ
キサントンなどの電子受容性物質やこれら電子吸
引物質を高分子化したものなどがある。
正孔輸送物質としては、ピレン、N−エチルカ
ルバゾール、N−イソナロピルカルバゾール2・
5−ビス(P−ジエチルアミノフエニル)−1・
3・4−オキサジアゾール、トリフエニルアミ
ン、ポリ−N−ビニルカルバゾール、ハロゲン化
ポリ−N−ビニルカルバゾール、ポリビニルピレ
ン、ポリビニルアントラセン、ポリビニルアクリ
ジン、ポリ−9−ビニルフエニルアントラセン、
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がある。
特に、電荷輸送物として適当なものは、特開昭
54−59143号、同54−150128号、同55−46760号、
同55−52063号、同55−52064号、同55−84943
号、同55−154955号、同55−156954号、同55−
157550号、同55−157551号各公報、特願昭55−
165065号、同55−165067号、同55−178532号、同
56−14515号、同56−30342号、同56−40145号、
明細書などに開示されたヒドラゾン化合物、特開
昭49−105537号、同54−74437号、同54−112637
号、同55−21080号、同55−32068号、同55−2285
号、同55−36849号、同55−51086号各公報などに
開示のピラゾリン化合物、特開昭51−94829号、
同51−94830号、同52−18323号、同53−27430
号、同53−147537号、同53−147539号、同54−
60928号、同54−61936号、同54−74437号、同54
−74437号、同55−33112号、同55−33113号、同
55−36849号各公報に開示されたエチレンまたは
ポリエン構造を有する化合物、特開昭51−96329
号、同52−124336号、同52−139063号、同52−
139064号、同52−139065号、同52−139066号、同
54−2739号、同54−5433号、同54−26741号、同
54−26742号、同55−21080号各公報などに開示さ
れたオキサジアゾール系化合物、特開昭51−
93224号、同55−77745号、同55−101953号各公報
などに開示されたアルカン化合物、特開昭55−
53334号、同55−53335号、同55−64243号、同55
−105251号、同55−155358号各公報に開示のスチ
リル染料などを挙げることができる。
好ましいヒドラゾン化合物としては、例えば、
などを挙げることができる。また、適当なピラゾ
リン化合物としては、例えば1−フエニル−3−
(4−N・N−ジエチルアミノスチリル)−5−
(4−N・N−ジエチルアミノフエニル)ピラゾ
リン、1−フエニル−3−(4−N・N−ジプロ
ピルアミノスチリル)−5−(4−N・N−ジプロ
ピルフエニル)ピラゾリン、1−〔ピリジル−
(2)〕−3−(4−N・N−ジエチルアミノスチリ
ル)−5−(4−N・N−ジエチルアミノフエニ
ル)ピラゾリン、1−〔キノリル−(2)〕−3−(4
−N・N−ジエチルアミノスチリル)−5−(4−
N・N−ジエチルアミノフエニル)ピラゾリン、
1−〔キノリル−(4)〕−3−(4−N・N−ジベン
ジルアミノスチリル)−5−(4−N・N−ジベン
ジルアミノフエニル)ピラゾリン、1−〔レピジ
ル−(2)〕−3−(4−N・N−ジフエニルアミノス
チリル)−5−(4−N・N−ジフエニルアミノフ
エニル)ピラゾリン、1−〔レピジル−(2)〕−3−
(4−N・N−ジエチルアミノスチリル)−5−
(4−N・N−ジエチルアミノフエニル)ピラゾ
リンなどを挙げることができる。その他の具体的
な化合物については、前述の特許公報を参照する
ことができる。これらの化合物は、1種または2
種以上組合せて用いることができる。
電荷輸送層は、前述の電荷輸送化合物と結着剤
とを適当な溶剤に溶解せしめた溶液を塗布し、乾
燥せしめることにより形成させることが好まし
い。ここに用いる結着剤としては、例えばポリエ
チレン、ポリプロピレン、アクリル樹脂、メタク
リル樹脂、塩化ビニル樹脂、酢酸ビニル樹脂、フ
エノール樹脂、エポキシ樹脂、ポリエステル樹
脂、ポリスルホン、アルキド樹脂、ポリカーボネ
ート、ポリウレタンあるいはこれらの樹脂の繰り
返し単位のうち2つ以上を含む共重合体樹脂など
を挙げることができ、特にポリエステル樹脂、ポ
リカーボネートが好ましいものである。また、ポ
リ−N−ビニルカルバゾールの様にそれ自身電荷
輸送能力をもつ光導電性ポリマーをバインダーと
しても使用することができる。
この結着剤と電荷輸送化合物との配合割合は、
結着剤100重量部当り電荷輸送化合物を10〜500重
量とすることが好ましい。この電荷輸送層の厚さ
は、2〜100ミクロン、好ましくは5〜30ミクロ
ンである。
本発明の電荷輸送層には、種々の添加剤を含有
させることができる。かかる添加剤としては、ジ
フエニル、塩化ジフエニル、O−タ−フエニル、
P−タ−フエニル、ジブチルフタレート、ジメチ
ルグリコールフタレート、ジオクチルフタレー
ト、トリフエニル燐酸、メチルナフタリン、ベン
ゾフエノン、塩素化パラフイン、ジラウリルチオ
プロピオネート、3・5−ジニトロサリチル酸、
各種フルオロカーボン類などを挙げることができ
る。
また、本発明の電荷輸送層を形成させる際に用
いる溶剤としては、多数の有用な有機溶剤を包含
している。代表的なものとして、例えばベンゼ
ン、ナフタリン、トルエン、キシレン、メシチレ
ン、クロロベンゼンなどの芳香族系炭化水素類、
アセトン、2−ブタノンなどのケトン類、塩化メ
チレン、クロロホルム、塩化エチレンなどのハロ
ゲン化脂肪族系炭化水素類、テトラヒドロフラ
ン、エチルエーテルなどの環状若しくは直鎖状の
エーテル類など、あるいはこれらの混合溶剤を挙
げることができる。
本発明の電子写真感光体は、導電層の上に前述
のビスアゾ顔料を絶縁性バインダーに分散したこ
とからなる感光層を形成させたものであつてもよ
く、あるいは電荷輸送物質と絶縁性バインダー
(バインダー自身がポリ−N−ビニルカルバゾー
ルの様な電荷輸送物質であつてもよい)からなる
電荷輸送媒体中に前述のビスアゾ顔料を分散させ
たことからなる感光層を導電層の上に形成させた
ものであつてもよい。この際に用いる絶縁性バイ
ンダーと電荷輸送物質としては、例えば特公昭52
−1667号、特開昭47−30328号、同47−18545号公
報などに開示されたものを用いることができる。
本発明の電子写真感光体に用いる支持体として
は、導電性が付与されていれば良く、従来用いら
れているいずれのタイプの導電層であつてもさし
つかえない。具体的にはアルミニウム、パナジウ
ム、モリブデン、クロム、カミウム、チタン、ニ
ツケル、銅、亜鉛、パラジウム、インジウム、
錫、白金、金、ステンレス銅、真ちゆうなどの金
属シートあるいは金属を蒸着あるいはラミネート
したプラスチツクシートなどを挙げることができ
る。
本発明の電子写真感光体は、電子写真複写機に
利用するのみならず、レーザープリンター、
CRTプリンター、電子写真式製版システムなど
の電子写真応用分野にも広く用いることができ
る。
本発明によれば、従来の有機光導電性材料を用
いた電子写真感光体に較べて、感度が著しく高感
度となり、しかも繰り返し帯電および露光を
10000回以上実施した時でも明部電位の増加と暗
部電位の低下を起こすことがない。
以下、本発明を実施例に従つて説明する。
実施例 1
アルミ板上に脱脂カゼインのアンモニア水溶液
(カゼイン11.29g、28%アンモニア水1g、水
222ml)をマイヤーバーで塗布乾燥し、塗工量1.0
g/m2の接着層を形成した。次に前記例示のビス
アゾ顔料No.1の5gとブチラール樹脂(ブチラ
ール化度63モル%)2gをエタノール95mlに溶か
した液と共にボールミルで40時間分散した後、接
着層上にマイヤーバーで塗工し、乾燥後の塗工量
が0.2g/m3の電荷発生層を形成した。
次に1−〔ピリジル−(2)〕−3−(4−N・N−
ジエチルアミノスチリル)−5−(4−N・N−ジ
エチルアミノフエニル)ピラゾリン5g、ポリ−
4・4′−ジオキシジフエニル−2・2′−プロパン
カーボネート(分子量30000)5gをテトラヒド
フラン70mlに溶かした液を電荷発生層上に塗布乾
燥し塗工量が10g/m2の電荷輸送層を形成した。
この様にして作成した電子写真感光体を20℃、65
%(相対湿度)で調湿度川口電機(株)製静電複写紙
試験装置MOdelSP−428を用いてスタチツク方式
で5KVでコロナ帯電し、暗所で10秒間保持した
後、照度5luxで露光し帯電特性を調べた。
初期電圧をVo(−v)暗所での10秒間の電位
保持率をVk(%)、半減衰露光量をE1/2(lux・
sec)とし、この感光体の帯電特性を第1表に示
す。
第1表
Vo:−600ボルト
Vk:90%
E1/2:13.5lux・sec
本実施例の電子写真感光体を円筒状シリンダー
に張りつけて、これを複写機(キヤノン(株)製
Canon Np5500を改造したもの)に装着した。こ
の複写機は、シリンダーの周囲に負極性帯電器、
露光光学系、現像器、転写帯電器を配置してお
り、シリンダーの回転に伴ない順次工程が行なわ
れ、転写紙に画像が得られる構成になつている。
本実施例の感光体では、明部露光量15lux・sec
で鮮明な画像が得られた。また、感光体を用いて
25000枚以上の複写を行なつても、得られた画像
は、何れも良好なものであつた。
実施例 2
前記実施例1の電子写真感光体で用いた電荷輸
送層中の1−〔ピリジル−(2)〕−3−(4−N・N
−ジエチルアミノスチリル)−5−(4−N・N−
ジエチルアミノフエニル)ピラゾリンに代えて前
記例示のヒドラゾン化合物No.1(4−N・N−
ジエチルアミノベンズアルデヒド−N・N−ジフ
エニルヒドラゾン)を用いたほかは、全く同様の
方法で電子写真感光体を調製した。
この感光体の帯電特性を前記実施例1と同様に
測定したところ、第2表に示す結果が得られた。
第2表
Vo:−600ボルト
Vk:91%
E1/2:10.5lux・sec
また、本実施例の感光体を実施例1で用いた複
写機に装着し、同様に画像を形成したが、カブリ
のない鮮明な画像が得られ、また25000枚以上の
複写を行なつても、得られた画像は何れも良好な
ものであつた。
さらに、前述のヒドラゾン化合物に代えて、前
記例示No.2(2−メトキシ−4−N・N−ジエ
チルアミノベンズアルデヒド−N・N−ジフエニ
ルヒドラゾン)、No.5(4−N・N−ジエチルア
ミノベンズアルデヒド−N−フエニル−N−α−
ナフチルヒドラゾン)、No.8(N・N−ジフエニ
ルヒドラジノ−3−メチリデン−9−エチルカル
バゾール)をそれぞれ電荷輸送層に用いたが、前
記と同様の結果が得られた。
実施例 3
実施例1で作成した電荷発生層の上に2・5−
ビス(4−N・N−ジエチルアミノフエニル)−
1・3・4−オキサジアゾーン5gと実施例1で
用いたポリカーボネート樹脂5gをテトラヒドロ
フラン70mlに溶かした液をマイヤーバーで塗工
し、乾燥後の塗工量を11g/m2とした。
作成した感光体の帯電測定を実施例1と全く同
様にして行いその特性値は第3表のとおりであつ
た。
第3表
Vo:−560ボルト
Vk:90%
E1/2:15.6lux・sec
また、本実施例の感光体を実施例1で用いた複
写機に装着し、同様に画像を形成したが、カブリ
のない鮮明な画像が得られ、また25000枚以上の
複写を行なつても、得られた画像は、何れも良好
なものであつた。
実施例 4〜33
下記第4表に示すビスアゾ顔料5gをそれぞれ
ポリエステル樹脂溶液(ポリエステルアドヒーシ
ブ49000、デユポン社製固形分20%)10gとテト
ラヒドロフラン80mlとともにボールミルで60時間
分散後、アルミ蒸着マイラーフイルムのアルミ面
にマイヤーバーで塗布し、乾燥後の塗工量を0.3
g/m2とした。
次に4−N・N−ジエチルアミノベンズアルデ
ヒド−N−フエニル−N−α−ナフチルヒドラゾ
ン(前記例示のヒドラゾン化合物No.4)5g、
実施例1で用いたポリカーボネート樹脂5gをテ
トラヒドロフラン70mlに溶解した液を電荷発生層
上にベーカーアプリケーターを用いて塗布、乾燥
し、10g/m2の電荷輸送層を形成した。この様に
して作成した感光体を実施例1と同様にして帯電
測定を行つたところ、第4表のとおりの結果を得
た。[Formula] or -COOR 3 , where R 3 and R 4 are hydrogen atoms or optionally substituted alkyl groups (e.g., methyl group, ethyl group, propyl group, iso-propyl group, butyl group, sec- Butyl group, t-butyl group, amyl group, t-amyl group, hexyl group, cyclohexyl group, octyl group, t-octyl group,
2-ethylhexyl group, nonyl group, octadecyl group, benzyl group, chlorobenzyl group, dichlorobenzyl group, methylbenzyl group, dimethylbenzyl group, 2-phenylethyl group, 3-phenylpropyl group, α-naphthylmethyl group, β- naphthylmethyl group, 2-α-naphthylethyl group) or aryl group (e.g. phenyl group, tolyl group, xylyl group, biphenyl group, chlorophenyl group, dichlorophenyl group, trichlorophenyl group, bromophenyl group, dibrophenyl group, Tribromophenyl group, methoxyphenyl group, ethoxyphenyl group, butoxyphenyl group, phenoxyphenyl group, nitrophenyl, cyanophenyl group, hydroxyphenyl group, carboxyphenyl group, N/N
-dimethylaminophenyl group, N・N-diethylaminophenyl group, N・N-dibenzylaminophenyl group, acetylphenyl group, benzoylphenyl group, methylthiophenyl group, ethylthiophenyl group, mercaptophenyl group enyl group, α-naphthyl group, β-naphthyl group, etc.). However, R 3 and
R 4 is never a hydrogen atom at the same time. Furthermore, when -COOR 3 , R 3 is never a hydrogen atom. R 1 and R 2 are optionally substituted alkyl groups (e.g., methyl group, ethyl group, propyl group, butyl group, t-butyl group, hexyl group, cyclohexyl group, octyl group, t-octyl group, 2
-ethylhexyl group, benzyl group, 2-phenylethyl group, α-naphthylmethyl group, β-naphthylmethyl group, methoxymethyl group, ethoxymethyl group, 2-methoxyethyl group, 2-ethoxyethyl group, 2-hydroxyethyl group, 2-carboxyethyl group, 2-hydroxypropyl group, 3-hydroxypropyl group, 3-sulfopropyl group, phenoxymethyl group, 2-phenoxyethyl group, 3-phenoxypropyl group, 4-phenoxybutyl group,
2-cyanoethyl group, 3-cyanopropyl group, acetylmethyl group, 2-acetylethyl group, 3-acetylpropyl group, benzoylmethyl group, 2-benzoylethyl group, 3-benzoylpropyl group,
Methoxymethoxymethyl group, 2-methoxymethoxyethyl group, 3-methoxymethoxypropyl group,
N・N-dimethylaminomethyl group, N・N-diethylaminomethyl group, N・N-dibenzylaminomethyl group, 2-N・N-diethylaminoethyl group, 2-N・N-dibenzylaminoethyl group, 3
-N・N-diethylaminopropyl group, 3-N・
N-diphenylaminopropyl group, 3-mercaltopropyl group, 4-mercaptobutyl group, 2-chloroethyl group, 3-chloropropyl group, 4-chlorobutyl group, 3-chlorobutyl group, phenylthiomethyl group, 2-phenyl group nylthioethyl group, 3-phenylthiopropyl group, etc.) or aryl group (e.g., phenyl group, tolyl group, xylyl group,
Biphenyl group, chlorophenyl group, dichlorophenyl group, trichlorophenyl group, bromophenyl group, nitrophenyl group, cyanophenyl group, methoxyphenyl group, ethoxyphenyl group, ethyl phenyl group, diethylphenyl group, propylphenyl group, phenylphenyl group Cyphenyl group, phenylthiophenyl group, carboxyphenyl group, hydroxyphenyl group, sulfophenyl group, N・N-dimethylaminophenyl group, N・N-diethylaminophenyl group, N・N-diphenylamino Phenyl group, N
-ethyl-N-methylaminophenyl group, acetylphenyl group, benzoylphenyl group, α-naphthyl group, β-naphthyl group, etc.). Specific examples of the bisazo pigment represented by the general formula [] are listed below. bisazo pigment These bisazo pigments are produced either by tetrazotizing the diamine compound represented by general formula (a) by a conventional method and then performing a diazo coupling reaction in the presence of a coupler and an alkali, or by diazotizing the diamine compound and then converting it into a tetrazonium salt. It can be easily prepared by isolating the compound using a borofluoride salt or zinc chloride and subjecting it to a coupling reaction in a solvent such as N.N-dimethylformamide or dimethyl sulfoxide in the presence of an alkali such as pyridine. General formula (a) (In the formula, A 1 , A 2 , R, n and m are synonyms as defined above.) These bisazo pigments may be used alone or in combination of two or more. The electrophotographic photoreceptor of the present invention has a photosensitive layer having a structure in which a charge generation layer containing the bisazo pigment described above is coated on a suitable support, and a charge transport layer is laminated on this charge generation layer. It can be created by using In this type of electrophotographic photoreceptor, an intermediate layer is provided on a suitable support, a charge generation layer containing the bisazo pigment described above is formed thereon, and a charge transport layer described below is formed on the intermediate layer. It's okay. This intermediate layer prevents the injection of free charges from the conductive support to the photosensitive layer when the photosensitive layer having a laminated structure is charged, and also serves as an adhesive that holds the photosensitive layer integrally bonded to the conductive support. It shows the action as a layer. This intermediate layer is made of metal oxide such as aluminum oxide, polyethylene, polypropylene, acrylic resin, methacrylic resin, vinyl chloride resin, phenolic resin, epoxy resin, polyester resin, alkyd resin, polycarbonate,
Polyurethane, polyimide resin, vinylidene chloride resin, vinyl chloride-vinyl acetate copolymer, casein, gelatin, polyvinyl alcohol, water-soluble polyethylene, nitrocellulose, etc. can be used. The thickness of this intermediate layer or adhesive layer is
A suitable value is 0.1μ to 5μ, preferably 0.5 to 3μ. Further, a laminated structure may be used in which the charge generation layer is provided on the charge transport layer, and in this case, an appropriate surface protection layer may be formed. The charge generation layer can be provided by means such as vacuum deposition, sputtering, glow discharge or coating depending on the type of charge generation material used. When coating, the charge-generating material is used as a binder.
There are cases where it is provided free, cases where it is provided as a resin dispersion, and cases where it is provided as a homogeneous solution of a binder and a charge generating material. In dispersing the bisazo pigment, known methods such as ball milling and attritor can be used, and it is desirable that the pigment particles be 5 microns or less, preferably 2 microns or less, most preferably 0.5 microns or less. The disazo pigment can also be applied by dissolving it in an amine solvent such as ethylenediamine. Conventional methods such as blade, Mayer bar, and spray dipping are used for application. The thickness of the charge generation layer is 5μ or less, preferably 0.01~
1μ is desirable. When using a binder in the charge generation layer, a large amount of binder will affect sensitivity, so the ratio of binder in the charge generation layer should be 80%.
% or less, preferably 40% or less. Binders used include polyvinyl butyral, polyvinyl acetate, polyester, polycarbonate, phenoxy resin, acrylic resin,
Polyacrylamide, polyamide, polyvinylpyridine resin, cellulose resin, urethane resin,
Various resins such as epoxy resin, casein, and polyvinyl alcohol are used. If necessary, the surface of the charge generation layer can be polished to a mirror finish in order to uniformly inject carriers into the charge transport layer above the charge generation layer. A charge transport layer is provided on the charge generation layer provided in this manner. If the charge transport material does not have film-forming ability, a charge transport layer is formed by applying a solution prepared by dissolving a binder in a suitable organic solvent and drying it by a conventional method.
Charge transport materials include electron transport materials and hole transport materials. Examples of electron transporting substances include chloranil, bromoanil, tetracyanoethylene, tetracyanoquinodimethane, 2,4,7-trinitro-9-fluorene, 2,4,5,7-tetranitrofluorenone, 2,4,7 - Electron-accepting substances such as trinitro-9-dicyanomethylenefluorenone, 2,4,5,7-tetranitroxanthone, and 2,4,8-trinitrothioxanthone, and polymerized versions of these electron-withdrawing substances. . As hole transport substances, pyrene, N-ethylcarbazole, N-isonalopylcarbazole 2.
5-bis(P-diethylaminophenyl)-1.
3,4-oxadiazole, triphenylamine, poly-N-vinylcarbazole, halogenated poly-N-vinylcarbazole, polyvinylpyrene, polyvinylanthracene, polyvinylacridine, poly-9-vinylphenylanthracene,
Examples include pyrene-formaldehyde resin and ethylcarbazole formaldehyde resin. In particular, those suitable as charge transporters are
No. 54-59143, No. 54-150128, No. 55-46760,
No. 55-52063, No. 55-52064, No. 55-84943
No. 55-154955, No. 55-156954, No. 55-
No. 157550, No. 55-157551, patent application No. 1575-
No. 165065, No. 55-165067, No. 55-178532, No.
No. 56-14515, No. 56-30342, No. 56-40145,
Hydrazone compounds disclosed in specifications, etc., JP-A-49-105537, JP-A-54-74437, JP-A-54-112637
No. 55-21080, No. 55-32068, No. 55-2285
Pyrazoline compounds disclosed in JP-A No. 55-36849, JP-A No. 55-51086, etc.;
No. 51-94830, No. 52-18323, No. 53-27430
No. 53-147537, No. 53-147539, No. 54-
No. 60928, No. 54-61936, No. 54-74437, No. 54
−74437, No. 55-33112, No. 55-33113, No.
Compounds having an ethylene or polyene structure disclosed in each publication of No. 55-36849, JP-A No. 51-96329
No. 52-124336, No. 52-139063, No. 52-
No. 139064, No. 52-139065, No. 52-139066, No. 139064, No. 52-139065, No. 52-139066, No.
No. 54-2739, No. 54-5433, No. 54-26741, No. 54-26741, No.
Oxadiazole compounds disclosed in JP-A-54-26742 and JP-A-55-21080, etc.
Alkane compounds disclosed in JP-A No. 93224, No. 55-77745, No. 55-101953, etc.
No. 53334, No. 55-53335, No. 55-64243, No. 55
Examples include styryl dyes disclosed in Publications No. 105251 and No. 55-155358. Preferred hydrazone compounds include, for example: etc. can be mentioned. In addition, suitable pyrazoline compounds include, for example, 1-phenyl-3-
(4-N・N-diethylaminostyryl)-5-
(4-N・N-diethylaminophenyl)pyrazoline, 1-phenyl-3-(4-N・N-dipropylaminostyryl)-5-(4-N・N-dipropylphenyl)pyrazoline, 1- [Pyridyl-
(2)]-3-(4-N・N-diethylaminostyryl)-5-(4-N・N-diethylaminophenyl)pyrazoline, 1-[quinolyl-(2)]-3-(4
-N・N-diethylaminostyryl)-5-(4-
N・N-diethylaminophenyl) pyrazoline,
1-[quinolyl-(4)]-3-(4-N・N-dibenzylaminostyryl)-5-(4-N・N-dibenzylaminophenyl)pyrazoline, 1-[lepidyl-(2) ]-3-(4-N·N-diphenylaminostyryl)-5-(4-N·N-diphenylaminophenyl)pyrazoline, 1-[lepidyl-(2)]-3-
(4-N・N-diethylaminostyryl)-5-
(4-N.N-diethylaminophenyl)pyrazoline and the like can be mentioned. For other specific compounds, reference can be made to the aforementioned patent publications. These compounds may be one or two
More than one species can be used in combination. The charge transport layer is preferably formed by applying a solution prepared by dissolving the above-mentioned charge transport compound and binder in a suitable solvent and drying the solution. Examples of the binder used here include polyethylene, polypropylene, acrylic resin, methacrylic resin, vinyl chloride resin, vinyl acetate resin, phenol resin, epoxy resin, polyester resin, polysulfone, alkyd resin, polycarbonate, polyurethane, or a combination of these resins. Examples include copolymer resins containing two or more repeating units, with polyester resins and polycarbonates being particularly preferred. Furthermore, photoconductive polymers that themselves have charge transporting ability, such as poly-N-vinylcarbazole, can also be used as binders. The blending ratio of this binder and charge transport compound is
Preferably, the charge transport compound is contained in an amount of 10 to 500 parts by weight per 100 parts by weight of the binder. The thickness of this charge transport layer is between 2 and 100 microns, preferably between 5 and 30 microns. The charge transport layer of the present invention can contain various additives. Such additives include diphenyl, diphenyl chloride, O-terphenyl,
P-terphenyl, dibutyl phthalate, dimethyl glycol phthalate, dioctyl phthalate, triphenyl phosphoric acid, methylnaphthalene, benzophenone, chlorinated paraffin, dilaurylthiopropionate, 3,5-dinitrosalicylic acid,
Examples include various fluorocarbons. Further, the solvent used in forming the charge transport layer of the present invention includes many useful organic solvents. Typical examples include aromatic hydrocarbons such as benzene, naphthalene, toluene, xylene, mesitylene, and chlorobenzene;
Ketones such as acetone and 2-butanone, halogenated aliphatic hydrocarbons such as methylene chloride, chloroform, and ethylene chloride, cyclic or linear ethers such as tetrahydrofuran and ethyl ether, or mixed solvents thereof. can be mentioned. The electrophotographic photoreceptor of the present invention may have a photosensitive layer formed by dispersing the above-mentioned bisazo pigment in an insulating binder on a conductive layer, or a charge transporting substance and an insulating binder ( A photosensitive layer was formed on the conductive layer by dispersing the bisazo pigment described above in a charge transport medium (the binder itself may be a charge transport substance such as poly-N-vinylcarbazole). It may be something. The insulating binder and charge transport material used in this case include, for example,
Those disclosed in Japanese Patent Application Laid-open No. 47-30328, Japanese Patent Application Publication No. 47-18545, etc. can be used. The support used in the electrophotographic photoreceptor of the present invention may be any type of conductive layer conventionally used as long as it is imparted with conductivity. Specifically, aluminum, panadium, molybdenum, chromium, camium, titanium, nickel, copper, zinc, palladium, indium,
Examples include metal sheets such as tin, platinum, gold, stainless copper, and brass, and plastic sheets on which metals are vapor-deposited or laminated. The electrophotographic photoreceptor of the present invention can be used not only for electrophotographic copying machines, but also for laser printers,
It can also be widely used in electrophotographic applications such as CRT printers and electrophotographic plate making systems. According to the present invention, the sensitivity is significantly higher than that of electrophotographic photoreceptors using conventional organic photoconductive materials, and moreover, repeated charging and exposure are not required.
There is no increase in bright area potential and no decrease in dark area potential even when the test is performed over 10,000 times. Hereinafter, the present invention will be explained according to examples. Example 1 An ammonia aqueous solution of defatted casein (11.29 g of casein, 1 g of 28% ammonia water, water) was placed on an aluminum plate.
222ml) with a Mayer bar and dry, coating amount 1.0
An adhesive layer of g/m 2 was formed. Next, 5 g of the above-exemplified bisazo pigment No. 1 and 2 g of butyral resin (butyralization degree 63 mol%) were dispersed in a ball mill for 40 hours with a solution dissolved in 95 ml of ethanol, and then coated on the adhesive layer with a Meyer bar. A charge generation layer having a coating weight of 0.2 g/m 3 after drying was formed. Next, 1-[pyridyl-(2)]-3-(4-N・N-
diethylaminostyryl)-5-(4-N・N-diethylaminophenyl)pyrazoline 5g, poly-
A solution prepared by dissolving 5 g of 4,4'-dioxydiphenyl-2,2'-propane carbonate (molecular weight 30,000) in 70 ml of tetrahydrofuran is applied onto the charge generation layer and dried to produce a charge with a coating amount of 10 g/ m2. A transport layer was formed.
The electrophotographic photoreceptor prepared in this way was heated at 20°C and 65°C.
% (relative humidity) Humidity control Electrostatic copying paper testing device MOdelSP-428 manufactured by Kawaguchi Electric Co., Ltd. was used to corona charge the sample at 5 KV using static method, and after holding it for 10 seconds in the dark, it was exposed to light at an illuminance of 5 lux and charged. We investigated the characteristics. The initial voltage is Vo (-v), the potential retention rate for 10 seconds in the dark is Vk (%), and the half-decay exposure is E1/2 (lux・
sec), and the charging characteristics of this photoreceptor are shown in Table 1. Table 1 Vo: -600 volts Vk: 90% E1/2: 13.5 lux・sec The electrophotographic photoreceptor of this example was attached to a cylindrical cylinder, and this was used in a copying machine (manufactured by Canon Inc.).
Attached to a modified Canon Np5500). This copier has a negative charger around the cylinder.
An exposure optical system, a developing device, and a transfer charger are arranged, and the steps are performed sequentially as the cylinder rotates to form an image on transfer paper. In the photoreceptor of this example, the bright area exposure was 15lux・sec.
A clear image was obtained. Also, using a photoreceptor
Even after more than 25,000 copies were made, all the images obtained were of good quality. Example 2 1-[pyridyl-(2)]-3-(4-N・N) in the charge transport layer used in the electrophotographic photoreceptor of Example 1
-diethylaminostyryl)-5-(4-N・N-
In place of pyrazoline (diethylaminophenyl), hydrazone compound No. 1 (4-N/N-
An electrophotographic photoreceptor was prepared in exactly the same manner except that diethylaminobenzaldehyde (N·N-diphenylhydrazone) was used. When the charging characteristics of this photoreceptor were measured in the same manner as in Example 1, the results shown in Table 2 were obtained. Table 2 Vo: -600 volts Vk: 91% E1/2: 10.5lux・sec Furthermore, the photoreceptor of this example was attached to the copying machine used in Example 1, and an image was formed in the same manner, but fogging occurred. Clear images without any blemishes were obtained, and even after more than 25,000 copies were made, all the images obtained were of good quality. Further, in place of the hydrazone compound described above, the example No. 2 (2-methoxy-4-N·N-diethylaminobenzaldehyde-N·N-diphenylhydrazone) and No. 5 (4-N·N-diethylaminobenzaldehyde) -N-phenyl-N-α-
Naphthylhydrazone) and No. 8 (N.N-diphenylhydrazino-3-methylidene-9-ethylcarbazole) were used in the charge transport layer, but the same results as above were obtained. Example 3 On the charge generation layer prepared in Example 1, 2.5-
Bis(4-N・N-diethylaminophenyl)-
A solution obtained by dissolving 5 g of 1,3,4-oxadiazone and 5 g of the polycarbonate resin used in Example 1 in 70 ml of tetrahydrofuran was applied using a Mayer bar, and the coating amount after drying was 11 g/m 2 . The electrostatic charge of the prepared photoreceptor was measured in exactly the same manner as in Example 1, and the characteristic values were as shown in Table 3. Table 3 Vo: -560 volts Vk: 90% E1/2: 15.6lux・sec Furthermore, the photoreceptor of this example was installed in the copying machine used in Example 1, and an image was formed in the same manner, but fogging occurred. Clear images without any blemishes were obtained, and even after more than 25,000 copies were made, all the images obtained were of good quality. Examples 4 to 33 5 g of the bisazo pigments shown in Table 4 below were dispersed in a ball mill for 60 hours with 10 g of a polyester resin solution (Polyester Adhesive 49000, manufactured by DuPont, solids content 20%) and 80 ml of tetrahydrofuran for 60 hours, and then aluminum-deposited Mylar film was dispersed. Apply it to the aluminum surface with a Mayer bar, and after drying, the coating amount is 0.3
g/ m2 . Next, 5 g of 4-N·N-diethylaminobenzaldehyde-N-phenyl-N-α-naphthylhydrazone (the above-mentioned hydrazone compound No. 4),
A solution obtained by dissolving 5 g of the polycarbonate resin used in Example 1 in 70 ml of tetrahydrofuran was applied onto the charge generation layer using a Baker applicator and dried to form a charge transport layer of 10 g/m 2 . When the photoreceptor thus prepared was subjected to charge measurement in the same manner as in Example 1, the results shown in Table 4 were obtained.
【表】【table】
【表】
また、実施例4〜33の電子写真感光体を実施例
1で用いた複写機に装着し、同様に画像を形成し
たが、カブリのない鮮明な画像が得られ、また
25000枚以上の複写を行なつても、得られた画像
は、何れも良好なものであつた。
実施例 34
ポリ−N−ビニルカルバゾール(分子量30万)
20g、2・4・7−トリニトロフルオレノン3.2
gポリエステル系樹脂溶液(ポリエステルアドヒ
ーシブ49000デユポン社製固形分20%)10gおよ
び前述のビスアゾ顔料No.2の20gをテトラヒド
ロフラン180mlをボールミルにチヤージし40時間
分散後アルミ蒸着マイラーフイルムのアルミ面上
にベーカーアプリケーターを用いて塗工し、乾燥
後の塗工量を12g/m2とした。
こうして作成した感光体を実施例1と同様にし
て帯電測定した結果を第5表に示す。但し帯電極
性はとした。
第5表
Vo:480ボルト
Vk:90%
E1/2:12.2lux・sec[Table] In addition, when the electrophotographic photoreceptors of Examples 4 to 33 were attached to the copying machine used in Example 1 and images were formed in the same manner, clear images without fogging were obtained.
Even after more than 25,000 copies were made, all the images obtained were of good quality. Example 34 Poly-N-vinylcarbazole (molecular weight 300,000)
20g, 2,4,7-trinitrofluorenone 3.2
g 10 g of polyester resin solution (Polyester Adhesive 49000 manufactured by Dupont, solid content 20%) and 20 g of the aforementioned bisazo pigment No. 2 were charged with 180 ml of tetrahydrofuran in a ball mill, dispersed for 40 hours, and then dispersed on the aluminum surface of an aluminum vapor-deposited mylar film. The coating was applied using a Baker applicator, and the coating weight after drying was 12 g/m 2 . Table 5 shows the results of charging measurement of the photoreceptor thus prepared in the same manner as in Example 1. However, the charging polarity was determined. Table 5 Vo: 480 volts Vk: 90% E1/2: 12.2lux・sec
Claims (1)
少なくとも1種を含有する感光層を有することを
特徴とする電子写真感光体。 一般式〔〕 (式中、Rは置換されてもよいアルキル基若しく
はアリール基を示す。A1およびA2は、置換され
てもよい2価の複素環基を示し、nおよびmは
0、1または2である。Cpは、カプラー残基を
示す。)[Scope of Claims] 1. An electrophotographic photoreceptor comprising a photosensitive layer containing at least one bisazo pigment represented by the following general formula []. General formula [] (In the formula, R represents an optionally substituted alkyl group or aryl group. A 1 and A 2 represent an optionally substituted divalent heterocyclic group, and n and m are 0, 1, or 2. (Cp indicates a coupler residue.)
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP8925581A JPS57204056A (en) | 1981-06-10 | 1981-06-10 | Electrophotographic receptor |
US06/381,577 US4427753A (en) | 1981-06-02 | 1982-05-24 | Electrophotographic photosensitive member with disazo or trisazo compound |
DE19823220772 DE3220772A1 (en) | 1981-06-02 | 1982-06-02 | LIGHT SENSITIVE ELEMENT FOR ELECTROPHOTOGRAPHIC PURPOSES |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP8925581A JPS57204056A (en) | 1981-06-10 | 1981-06-10 | Electrophotographic receptor |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS57204056A JPS57204056A (en) | 1982-12-14 |
JPS6261258B2 true JPS6261258B2 (en) | 1987-12-21 |
Family
ID=13965650
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP8925581A Granted JPS57204056A (en) | 1981-06-02 | 1981-06-10 | Electrophotographic receptor |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS57204056A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2021044850A1 (en) * | 2019-09-05 | 2021-03-11 | パナソニックIpマネジメント株式会社 | Touch sensor and method for manufacturing touch sensor |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP3563916B2 (en) * | 1996-04-26 | 2004-09-08 | キヤノン株式会社 | Electrophotographic photoreceptor, electrophotographic apparatus and process cartridge using the electrophotographic photoreceptor |
-
1981
- 1981-06-10 JP JP8925581A patent/JPS57204056A/en active Granted
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2021044850A1 (en) * | 2019-09-05 | 2021-03-11 | パナソニックIpマネジメント株式会社 | Touch sensor and method for manufacturing touch sensor |
Also Published As
Publication number | Publication date |
---|---|
JPS57204056A (en) | 1982-12-14 |
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