JPH01179160A - Electrophotographic sensitive body - Google Patents
Electrophotographic sensitive bodyInfo
- Publication number
- JPH01179160A JPH01179160A JP204188A JP204188A JPH01179160A JP H01179160 A JPH01179160 A JP H01179160A JP 204188 A JP204188 A JP 204188A JP 204188 A JP204188 A JP 204188A JP H01179160 A JPH01179160 A JP H01179160A
- Authority
- JP
- Japan
- Prior art keywords
- group
- carrier
- layer
- photoreceptor
- formula
- 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.)
- Pending
Links
- -1 bisazo compound Chemical class 0.000 claims abstract description 46
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 4
- 108091008695 photoreceptors Proteins 0.000 claims description 67
- 239000000126 substance Substances 0.000 claims description 52
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 abstract description 23
- 230000035945 sensitivity Effects 0.000 abstract description 11
- 239000000463 material Substances 0.000 abstract description 10
- 239000006185 dispersion Substances 0.000 abstract description 9
- 239000011248 coating agent Substances 0.000 abstract description 7
- 238000000576 coating method Methods 0.000 abstract description 7
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 6
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 abstract description 4
- 239000000049 pigment Substances 0.000 abstract description 3
- 229910052736 halogen Inorganic materials 0.000 abstract description 2
- 150000002367 halogens Chemical class 0.000 abstract description 2
- 125000003107 substituted aryl group Chemical group 0.000 abstract 2
- 239000000758 substrate Substances 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 67
- 125000003118 aryl group Chemical group 0.000 description 13
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 12
- 125000000217 alkyl group Chemical group 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- 239000004431 polycarbonate resin Substances 0.000 description 9
- 229920005668 polycarbonate resin Polymers 0.000 description 9
- 239000011230 binding agent Substances 0.000 description 8
- 239000004419 Panlite Substances 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 238000005259 measurement Methods 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 239000003963 antioxidant agent Substances 0.000 description 5
- 235000006708 antioxidants Nutrition 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000000047 product 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
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-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
- SPVVMXMTSODFPU-UHFFFAOYSA-N 3-methyl-n-(3-methylbutyl)butan-1-amine Chemical compound CC(C)CCNCCC(C)C SPVVMXMTSODFPU-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000257465 Echinoidea Species 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229920000180 alkyd Polymers 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 229910052980 cadmium sulfide Inorganic materials 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 125000004663 dialkyl amino group Chemical group 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
- 239000002612 dispersion medium Substances 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- YDSWCNNOKPMOTP-UHFFFAOYSA-N mellitic acid Chemical compound OC(=O)C1=C(C(O)=O)C(C(O)=O)=C(C(O)=O)C(C(O)=O)=C1C(O)=O YDSWCNNOKPMOTP-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- JACMPVXHEARCBO-UHFFFAOYSA-N n-pentylpentan-1-amine Chemical compound CCCCCNCCCCC JACMPVXHEARCBO-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 239000011241 protective layer Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- NMNSBFYYVHREEE-UHFFFAOYSA-N 1,2-dinitroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C([N+]([O-])=O)C([N+](=O)[O-])=CC=C3C(=O)C2=C1 NMNSBFYYVHREEE-UHFFFAOYSA-N 0.000 description 1
- IZUKQUVSCNEFMJ-UHFFFAOYSA-N 1,2-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1[N+]([O-])=O IZUKQUVSCNEFMJ-UHFFFAOYSA-N 0.000 description 1
- WDCYWAQPCXBPJA-UHFFFAOYSA-N 1,3-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC([N+]([O-])=O)=C1 WDCYWAQPCXBPJA-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
- WPMHMYHJGDAHKX-UHFFFAOYSA-N 1-ethenylpyrene Chemical compound C1=C2C(C=C)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 WPMHMYHJGDAHKX-UHFFFAOYSA-N 0.000 description 1
- JIYMTJFAHSJKJZ-UHFFFAOYSA-N 1-n,4-n-ditert-butyl-1-n,4-n-dimethylbenzene-1,4-diamine Chemical compound CC(C)(C)N(C)C1=CC=C(N(C)C(C)(C)C)C=C1 JIYMTJFAHSJKJZ-UHFFFAOYSA-N 0.000 description 1
- KWLXMHPDSIQHDF-UHFFFAOYSA-N 10-methyl-n-(10-methylundecyl)undecan-1-amine Chemical compound CC(C)CCCCCCCCCNCCCCCCCCCC(C)C KWLXMHPDSIQHDF-UHFFFAOYSA-N 0.000 description 1
- BIEFDNUEROKZRA-UHFFFAOYSA-N 2-(2-phenylethenyl)aniline Chemical class NC1=CC=CC=C1C=CC1=CC=CC=C1 BIEFDNUEROKZRA-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- FEXBEKLLSUWSIM-UHFFFAOYSA-N 2-Butyl-4-methylphenol Chemical compound CCCCC1=CC(C)=CC=C1O FEXBEKLLSUWSIM-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- BHIIOLWIZLICII-UHFFFAOYSA-N 2-butyl-5-methylphenol Chemical compound CCCCC1=CC=C(C)C=C1O BHIIOLWIZLICII-UHFFFAOYSA-N 0.000 description 1
- RPLZABPTIRAIOB-UHFFFAOYSA-N 2-chloro-5-dodecylbenzene-1,4-diol Chemical compound CCCCCCCCCCCCC1=CC(O)=C(Cl)C=C1O RPLZABPTIRAIOB-UHFFFAOYSA-N 0.000 description 1
- ZNQOWAYHQGMKBF-UHFFFAOYSA-N 2-dodecylbenzene-1,4-diol Chemical compound CCCCCCCCCCCCC1=CC(O)=CC=C1O ZNQOWAYHQGMKBF-UHFFFAOYSA-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
- BSJQLOWJGYMBFP-UHFFFAOYSA-N 2-methyl-5-(2,4,4-trimethylpentan-2-yl)benzene-1,4-diol Chemical compound CC1=CC(O)=C(C(C)(C)CC(C)(C)C)C=C1O BSJQLOWJGYMBFP-UHFFFAOYSA-N 0.000 description 1
- KCXONTAHNOAWQJ-UHFFFAOYSA-N 2-methyl-5-octadec-2-enylbenzene-1,4-diol Chemical compound CCCCCCCCCCCCCCCC=CCC1=CC(O)=C(C)C=C1O KCXONTAHNOAWQJ-UHFFFAOYSA-N 0.000 description 1
- NJBCRXCAPCODGX-UHFFFAOYSA-N 2-methyl-n-(2-methylpropyl)propan-1-amine Chemical compound CC(C)CNCC(C)C NJBCRXCAPCODGX-UHFFFAOYSA-N 0.000 description 1
- 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 1
- XOUQAVYLRNOXDO-UHFFFAOYSA-N 2-tert-butyl-5-methylphenol Chemical compound CC1=CC=C(C(C)(C)C)C(O)=C1 XOUQAVYLRNOXDO-UHFFFAOYSA-N 0.000 description 1
- JFGQHAHJWJBOPD-UHFFFAOYSA-N 3-hydroxy-n-phenylnaphthalene-2-carboxamide Chemical compound OC1=CC2=CC=CC=C2C=C1C(=O)NC1=CC=CC=C1 JFGQHAHJWJBOPD-UHFFFAOYSA-N 0.000 description 1
- ITUYMTWJWYTELW-UHFFFAOYSA-N 4-chloroiminocyclohexa-2,5-dien-1-one Chemical compound ClN=C1C=CC(=O)C=C1 ITUYMTWJWYTELW-UHFFFAOYSA-N 0.000 description 1
- FUGYGGDSWSUORM-UHFFFAOYSA-N 4-hydroxystyrene Chemical compound OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 description 1
- WWDQROFMFKRUIF-UHFFFAOYSA-N 4-methyl-n-(4-methylpentyl)pentan-1-amine Chemical compound CC(C)CCCNCCCC(C)C WWDQROFMFKRUIF-UHFFFAOYSA-N 0.000 description 1
- ROFZMKDROVBLNY-UHFFFAOYSA-N 4-nitro-2-benzofuran-1,3-dione Chemical compound [O-][N+](=O)C1=CC=CC2=C1C(=O)OC2=O ROFZMKDROVBLNY-UHFFFAOYSA-N 0.000 description 1
- OTLNPYWUJOZPPA-UHFFFAOYSA-N 4-nitrobenzoic acid Chemical compound OC(=O)C1=CC=C([N+]([O-])=O)C=C1 OTLNPYWUJOZPPA-UHFFFAOYSA-N 0.000 description 1
- MMVIDXVHQANYAE-UHFFFAOYSA-N 5-nitro-2-benzofuran-1,3-dione Chemical compound [O-][N+](=O)C1=CC=C2C(=O)OC(=O)C2=C1 MMVIDXVHQANYAE-UHFFFAOYSA-N 0.000 description 1
- MEXUTNIFSHFQRG-UHFFFAOYSA-N 6,7,12,13-tetrahydro-5h-indolo[2,3-a]pyrrolo[3,4-c]carbazol-5-one Chemical compound C12=C3C=CC=C[C]3NC2=C2NC3=CC=C[CH]C3=C2C2=C1C(=O)NC2 MEXUTNIFSHFQRG-UHFFFAOYSA-N 0.000 description 1
- JCKVKMNRMJLTGO-UHFFFAOYSA-N 6-methyl-n-(6-methylheptyl)heptan-1-amine Chemical compound CC(C)CCCCCNCCCCCC(C)C JCKVKMNRMJLTGO-UHFFFAOYSA-N 0.000 description 1
- KHFRJOPGKUBZLL-UHFFFAOYSA-N 7-methyl-n-(7-methyloctyl)octan-1-amine Chemical compound CC(C)CCCCCCNCCCCCCC(C)C KHFRJOPGKUBZLL-UHFFFAOYSA-N 0.000 description 1
- IFJNFWJTPMJATL-UHFFFAOYSA-N 7-tert-butyl-2,2,4-trimethyl-3,4-dihydrochromen-6-ol Chemical compound CC(C)(C)C1=C(O)C=C2C(C)CC(C)(C)OC2=C1 IFJNFWJTPMJATL-UHFFFAOYSA-N 0.000 description 1
- XQHDBRUVHVNIHR-UHFFFAOYSA-N 8-methyl-n-(8-methylnonyl)nonan-1-amine Chemical compound CC(C)CCCCCCCNCCCCCCCC(C)C XQHDBRUVHVNIHR-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- OUBMGJOQLXMSNT-UHFFFAOYSA-N N-isopropyl-N'-phenyl-p-phenylenediamine Chemical compound C1=CC(NC(C)C)=CC=C1NC1=CC=CC=C1 OUBMGJOQLXMSNT-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- QHWKHLYUUZGSCW-UHFFFAOYSA-N Tetrabromophthalic anhydride Chemical compound BrC1=C(Br)C(Br)=C2C(=O)OC(=O)C2=C1Br QHWKHLYUUZGSCW-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 229920002433 Vinyl chloride-vinyl acetate copolymer Polymers 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000000641 acridinyl group Chemical class C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 229940087168 alpha tocopherol Drugs 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 1
- 229940027998 antiseptic and disinfectant acridine derivative Drugs 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- 238000007611 bar coating method Methods 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 150000001907 coumarones Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 1
- LAWOZCWGWDVVSG-UHFFFAOYSA-N dioctylamine Chemical compound CCCCCCCCNCCCCCCCC LAWOZCWGWDVVSG-UHFFFAOYSA-N 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- PWWSSIYVTQUJQQ-UHFFFAOYSA-N distearyl thiodipropionate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCCCCCC PWWSSIYVTQUJQQ-UHFFFAOYSA-N 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 150000002461 imidazolidines Chemical class 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 229940102253 isopropanolamine Drugs 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- NNYHMCFMPHPHOQ-UHFFFAOYSA-N mellitic anhydride Chemical compound O=C1OC(=O)C2=C1C(C(OC1=O)=O)=C1C1=C2C(=O)OC1=O NNYHMCFMPHPHOQ-UHFFFAOYSA-N 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- GMTCPFCMAHMEMT-UHFFFAOYSA-N n-decyldecan-1-amine Chemical compound CCCCCCCCCCNCCCCCCCCCC GMTCPFCMAHMEMT-UHFFFAOYSA-N 0.000 description 1
- MJCJUDJQDGGKOX-UHFFFAOYSA-N n-dodecyldodecan-1-amine Chemical compound CCCCCCCCCCCCNCCCCCCCCCCCC MJCJUDJQDGGKOX-UHFFFAOYSA-N 0.000 description 1
- PXSXRABJBXYMFT-UHFFFAOYSA-N n-hexylhexan-1-amine Chemical compound CCCCCCNCCCCCC PXSXRABJBXYMFT-UHFFFAOYSA-N 0.000 description 1
- MFHKEJIIHDNPQE-UHFFFAOYSA-N n-nonylnonan-1-amine Chemical compound CCCCCCCCCNCCCCCCCCC MFHKEJIIHDNPQE-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- 150000002898 organic sulfur compounds Chemical class 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 150000007978 oxazole derivatives Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 125000005504 styryl group Chemical class 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- AUHHYELHRWCWEZ-UHFFFAOYSA-N tetrachlorophthalic anhydride Chemical compound ClC1=C(Cl)C(Cl)=C2C(=O)OC(=O)C2=C1Cl AUHHYELHRWCWEZ-UHFFFAOYSA-N 0.000 description 1
- NLDYACGHTUPAQU-UHFFFAOYSA-N tetracyanoethylene Chemical group N#CC(C#N)=C(C#N)C#N NLDYACGHTUPAQU-UHFFFAOYSA-N 0.000 description 1
- PCCVSPMFGIFTHU-UHFFFAOYSA-N tetracyanoquinodimethane Chemical compound N#CC(C#N)=C1C=CC(=C(C#N)C#N)C=C1 PCCVSPMFGIFTHU-UHFFFAOYSA-N 0.000 description 1
- LVEOKSIILWWVEO-UHFFFAOYSA-N tetradecyl 3-(3-oxo-3-tetradecoxypropyl)sulfanylpropanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCC LVEOKSIILWWVEO-UHFFFAOYSA-N 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 150000007979 thiazole derivatives Chemical class 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- CFAVHELRAWFONI-UHFFFAOYSA-N tris(2,4-dibutylphenyl) phosphite Chemical compound CCCCC1=CC(CCCC)=CC=C1OP(OC=1C(=CC(CCCC)=CC=1)CCCC)OC1=CC=C(CCCC)C=C1CCCC CFAVHELRAWFONI-UHFFFAOYSA-N 0.000 description 1
- IUURMAINMLIZMX-UHFFFAOYSA-N tris(2-nonylphenyl)phosphane Chemical compound CCCCCCCCCC1=CC=CC=C1P(C=1C(=CC=CC=1)CCCCCCCCC)C1=CC=CC=C1CCCCCCCCC IUURMAINMLIZMX-UHFFFAOYSA-N 0.000 description 1
- OBNYHQVOFITVOZ-UHFFFAOYSA-N tris[2,3-di(nonyl)phenyl]phosphane Chemical compound CCCCCCCCCC1=CC=CC(P(C=2C(=C(CCCCCCCCC)C=CC=2)CCCCCCCCC)C=2C(=C(CCCCCCCCC)C=CC=2)CCCCCCCCC)=C1CCCCCCCCC OBNYHQVOFITVOZ-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
- 235000004835 α-tocopherol 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
- G03G5/0666—Dyes containing a methine or polymethine group
- G03G5/0668—Dyes containing a methine or polymethine group containing only one methine or polymethine group
- G03G5/067—Dyes containing a methine or polymethine group containing only one methine or polymethine group containing hetero rings
-
- 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
- G03G5/0679—Disazo dyes
- G03G5/0683—Disazo dyes containing polymethine or anthraquinone groups
- G03G5/0685—Disazo dyes containing polymethine or anthraquinone groups containing hetero rings in the part of the molecule between the azo-groups
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Photoreceptors In Electrophotography (AREA)
Abstract
Description
【発明の詳細な説明】
［産業上の利用分野］
本発明は電子写真感光体に関し、詳しくは特定のビスア
ゾ化合物を含有する感光層を有する電子写真感光体に１
１１゛りる。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to an electrophotographic photoreceptor, and more specifically, the present invention relates to an electrophotographic photoreceptor having a photosensitive layer containing a specific bisazo compound.
11゛riru.
［従来の技術］
従来、電子写真感光体どしては、セレン、酸化亜鉛、硫
化カドミウム、シリコン等の無機光導電性化合物を主成
分とする感光層を右する無機感光体が広く用いられ【き
た。しかし、これらは感度、熱安定性、耐湿性、耐久性
等にＪ３いて必ずしも満足し得るものではない。例えば
、セレンは結晶化Ｊると感光体としての特性が劣化して
しまうため、製造上も難しく、また熱や指紋等が原因と
なり結晶化し、感光体としての性能が劣化してしまう。[Prior Art] Conventionally, inorganic photoreceptors with a photosensitive layer mainly composed of an inorganic photoconductive compound such as selenium, zinc oxide, cadmium sulfide, or silicon have been widely used as electrophotographic photoreceptors. came. However, these do not necessarily satisfy J3 in terms of sensitivity, thermal stability, moisture resistance, durability, etc. For example, when selenium crystallizes, its properties as a photoreceptor deteriorate, making it difficult to manufacture.Also, selenium crystallizes due to heat, fingerprints, etc., and its performance as a photoreceptor deteriorates.
また硫化カドミウムでは耐湿性や耐久性、酸化亜鉛でも
耐久性等に問題がある。In addition, cadmium sulfide has problems with moisture resistance and durability, and zinc oxide has problems with durability, etc.
これら無機感光体の持つ欠点を克服する目的で様々な有
機光Ｓ電性化合物を主成分とする感光層を有する有機感
光体の研究・開発が近年盛んに行なわれている。例えば
特公昭５Ｇ−１０４９６号にはポリ−Ｎ−ビニルカルバ
ゾールと２．４．７−ドリニトロー９−フルオレノンを
含有する感光層を有する有機感光体の記載がある。しか
しこの感光体は、感度及び耐久性において必ずしも満足
できるものではない。このような欠点を改良するために
キャリア発生機能とキャリア輸送機能とを異なる物質に
分担させ、より高性能の有機感光体を開発する試みがな
されている。このようないわゆる機能分離型の感光体は
、それぞれの材料を広い範囲から選択することができ、
任意の性能を有する感光体を比較的容易に作製し得るこ
とがら多くの研究がなされてきた。In order to overcome these drawbacks of inorganic photoreceptors, research and development have been actively conducted in recent years on organic photoreceptors having photosensitive layers containing various organic photo-S conductive compounds as main components. For example, Japanese Patent Publication No. 5G-10496 describes an organic photoreceptor having a photosensitive layer containing poly-N-vinylcarbazole and 2,4,7-dolinitro-9-fluorenone. However, this photoreceptor is not necessarily satisfactory in sensitivity and durability. In order to improve these drawbacks, attempts have been made to develop organic photoreceptors with higher performance by assigning the carrier generation function and the carrier transport function to different substances. For such so-called functionally separated photoreceptors, each material can be selected from a wide range.
Many studies have been conducted on the ability to relatively easily produce photoreceptors with arbitrary performance.
［発明が解決しようとする問題点］
上記のような機能分離型の感光体において、そのキャリ
ア発生物質として、数多くの化合物が提案されている。[Problems to be Solved by the Invention] Many compounds have been proposed as carrier-generating substances in the functionally separated type photoreceptor as described above.
無機化合物をキャリア発生物質として用いる例としては
、例えば、特公昭４３−１６１９８号に記載された無定
形セレンがあり、これは有機光導電性化合物と組合せて
使用されるが、無定形セレンからなるキャリア発生層は
熱により結晶化して感光体としての特性が劣化してしま
うという欠点は改良されてはいない。An example of using an inorganic compound as a carrier generating substance is, for example, amorphous selenium described in Japanese Patent Publication No. 43-16198, which is used in combination with an organic photoconductive compound. The disadvantage that the carrier generation layer crystallizes due to heat and deteriorates the characteristics as a photoreceptor has not been improved.
また有情染料や有線顔料をキャリア発生物質として用い
る電子写真感光体も数多く提案されている。例えば、ビ
スアゾ化合物を感光層中に含有する電子写真感光体とし
て、特開昭５４−２２８３４号、同５５−７３０５７号
、同５５−１１７１５１Ｍ、同５６−４６２３７Ｑ等が
すでに公知である。しかしこれらのビスアゾ化合物は感
度、残留電位あるいは、繰返し使用時の安定性の特性に
おいて、必ずしも満足し得るものではなく、また、キャ
リア輸送物質の選択範囲も限定されるなど、電子写真プ
ロセスの幅広い要求を十分満足させるものではない。In addition, many electrophotographic photoreceptors have been proposed that use sentient dyes or wired pigments as carrier-generating substances. For example, as electrophotographic photoreceptors containing a bisazo compound in the photosensitive layer, JP-A-54-22834, JP-A-55-73057, JP-A-55-117151M, and JP-A-56-46237Q are already known. However, these bisazo compounds do not necessarily satisfy the characteristics of sensitivity, residual potential, or stability during repeated use, and the range of selection of carrier transport materials is also limited, which makes them difficult to meet the wide demands of electrophotographic processes. It does not fully satisfy.
［発明の目的］
本発明の第１の目的はキャリア発生能に優れた特定のビ
スアゾ化合物を含有する電子写真感光体を提供すること
にある。[Object of the Invention] The first object of the present invention is to provide an electrophotographic photoreceptor containing a specific bisazo compound having excellent carrier generation ability.
本発明の第２の目的は、高感度でかつ残留電位が小さく
、また耐久性が轟く更に繰返し使用してもそれらの特性
が変化しない耐用性の優れた電子写真感光体を提供する
ことにある。A second object of the present invention is to provide an electrophotographic photoreceptor that is highly sensitive, has a low residual potential, is extremely durable, and does not change its characteristics even after repeated use. .
本発明の第３の目的は、広範なキャリア輸送物質との組
合せにおいても、有効にキャリア発生物質として作用し
得るビスアゾ化合物を含有する電子写真感光体を提供す
ることにある。A third object of the present invention is to provide an electrophotographic photoreceptor containing a bisazo compound that can effectively act as a carrier-generating substance even in combination with a wide variety of carrier-transporting substances.
本発明のその他の目的は、明ｌｌＩ書中の記載から明ら
かになるであろう。Other objects of the invention will become apparent from the description in Book II.
［問題点を解決するための手段］
本発明者等は、以上の目的を達成すべく鋭意研究を重ね
た結果、下記一般式［Ｉ］で示されるビスアゾ化合物が
電子写真感光体の優れた有効成分として働き得る事を見
出し、本発明を完成したものである。[Means for Solving the Problems] As a result of intensive research to achieve the above object, the present inventors have found that a bisazo compound represented by the following general formula [I] has excellent effectiveness in electrophotographic photoreceptors. The present invention was completed by discovering that it can function as a component.
一般式［Ｉ］
Ｉ
式中、Ｃｐはカプラー残基を表ねず。×１は水素原子、
シアノ基又はハロゲン原子を表わし、×２はゝＮ＋−１
．−０−又は−Ｓ−を表わす。General formula [I] I In the formula, Cp does not represent a coupler residue. ×1 is a hydrogen atom,
Represents a cyano group or a halogen atom, ×2 is ゝN+-1
．． -0- or -S-.
Ｃｐはカプラー残塁を表わし、下記一般式（１）〜（１
１）で示Ｊカプラー残基が好ましい。Cp represents coupler remaining bases, and is expressed by the following general formulas (1) to (1
J coupler residues shown in 1) are preferred.
（？） （８）υｈ
式中、２はベンゼン環と縮合して多環式芳香族環あるい
は複素環を形成するに必要な原子群を表わす。(?) (8) υh In the formula, 2 represents an atomic group necessary to form a polycyclic aromatic ring or a heterocycle by condensation with a benzene ring.
Ｒ１，Ｒ２は水素原子、アルキル基、アラルキル基、ア
リール基、複素環基あるいはそれらの置換体を表わす。R1 and R2 represent a hydrogen atom, an alkyl group, an aralkyl group, an aryl group, a heterocyclic group, or a substituted product thereof.
また窒素原子あるいは炭素原子と共に環を形成してもよ
い。Further, it may form a ring together with a nitrogen atom or a carbon atom.
Ｒ３はＯ，Ｓ、−ＮＨを表わす。R3 represents O, S, -NH.
Ｒ４、Ｒｓは水素原子、アルキル基、アルコキシ基、ニ
ドｏｌ、シアノ基、ハロゲン原子、アセチル基を表わす
。R4 and Rs represent a hydrogen atom, an alkyl group, an alkoxy group, a cyano group, a halogen atom, or an acetyl group.
Ｙは５員環、６員環を形成するに必要な原子群を表わす
。Y represents an atomic group necessary to form a 5-membered ring or a 6-membered ring.
Ａは炭素環式芳香族環又は複素環式芳香族環の２価の基
を表わす。A represents a divalent group of a carbocyclic aromatic ring or a heterocyclic aromatic ring.
Ｒ６はアルキル基、アラルキル基、アリール基、複素環
基あるいはそれらの置換体を表わす。R6 represents an alkyl group, an aralkyl group, an aryl group, a heterocyclic group, or a substituted product thereof.
Ｒ７は水素原子、アルキル基、ジアルキルアミＬＬジア
リールアミムＬジアラルキルアミノ基、カルバモイル基
、カルボキシ基またはそのエステル基を表わす。R7 represents a hydrogen atom, an alkyl group, a dialkylamino group, a carbamoyl group, a carboxy group, or an ester group thereof.
Ｒ８は芳香族環基あるいはその置換体を表わす。R8 represents an aromatic ring group or a substituted product thereof.
前記２の芳香族環としては、ベンゼン、ナフタレンなど
があり、複素環としてはインドール、カルバゾール、ベ
ンゾフラン、ジベンゾフランなどがある。Ｚは置換基を
有してもよく、置換基としては、ハロゲン原子（例えば
フッ素原子、塩素原子、臭素原子など）、アルキル基（
例えばメチル基、エチル基、プロピル基、ブチル基など
）、アルコキシ基（例えばメトキシ基、エトキシ基、プ
ロポキシ基、ブトキシ基など）、ニトロ基などがあげら
れる。Examples of the above-mentioned 2 aromatic rings include benzene and naphthalene, and examples of the heterocycle include indole, carbazole, benzofuran, and dibenzofuran. Z may have a substituent, and examples of the substituent include a halogen atom (for example, a fluorine atom, a chlorine atom, a bromine atom, etc.), an alkyl group (
Examples include methyl group, ethyl group, propyl group, butyl group, etc.), alkoxy groups (eg, methoxy group, ethoxy group, propoxy group, butoxy group, etc.), and nitro group.
Ｒ１，Ｒ２のアルキル基としてはメチル基、エチル基、
プロピル基、ブチル基などがあり、アラルキル基として
はベンジル基、フェネチル基であり、アリール基として
は、フェニル基、ナフチル基、ジフェニル基などである
。複素環基としてはフリル基、チエニル基、インドリル
基、カルバゾリル基、ベンゾカルバゾリル基、ピリジル
基などがある。これらは前記の如き置換基で置換されて
もよい。置換基としては、ハロゲン原子（フッ素原子、
塩素原子、臭素原子など）、アルキル基（メチル基、エ
チル基、プロピル基、ブチル基など）、アルコキシ基（
メトキシ基、エトキシ基、プロポキシ基、ブトキシ基な
ど）、ジメチルアミノ基、ジエチルアミノ基、ジフェニ
ルアミノ基などの置換アミノ基、トリクロロメチル、ト
リフルオロメチルなどのハロアルキル基、ニトロ基、シ
アン基、カルボキシ基またはそのエステル基、ヒドロキ
シ基などがあげられる。The alkyl groups for R1 and R2 include methyl group, ethyl group,
Examples of the aralkyl group include a benzyl group and a phenethyl group, and examples of the aryl group include a phenyl group, a naphthyl group, and a diphenyl group. Examples of the heterocyclic group include furyl group, thienyl group, indolyl group, carbazolyl group, benzocarbazolyl group, and pyridyl group. These may be substituted with the substituents described above. Substituents include halogen atoms (fluorine atoms,
chlorine atom, bromine atom, etc.), alkyl group (methyl group, ethyl group, propyl group, butyl group, etc.), alkoxy group (
(methoxy group, ethoxy group, propoxy group, butoxy group, etc.), substituted amino groups such as dimethylamino group, diethylamino group, diphenylamino group, haloalkyl group such as trichloromethyl, trifluoromethyl, nitro group, cyan group, carboxy group, Examples include ester groups and hydroxy groups.
Ｒ６はＲ＋ 、Ｒ２で示されたものと同じものをあげる
ことができる。R6 can be the same as R+ and R2.
Ａは０−フェニレン、０−ナフチレン基、１゜２−アン
トラキノニレン基、９．１０−フエナントリレン基等の
芳香族炭化水素の２価基や、３゜４−ピラゾールジイル
基、２．３−ピリジンジイル基、４．５−ピリミジンジ
イル基、６，７−インダゾールジイル基、５．６−ベン
ゾイミダゾール基、６．７−キラジイル基等の複素環２
価基があげられる。これらは置換基を有してもよく、ア
ルキル基（メチル基、エチル基、プロピル基、ブチル基
など）、アルコキシ基（メトキシ基、エトキシ基、プロ
ポキシ基、ブトキシ基など）、ハロゲン原子（フッ素原
子、塩素原子、臭素原子など）、アルキルアミノ基（メ
チルアミノ基、エチルアミノ基など）、ジアルキルアミ
ノ基（ジメチルアミノ基、ジエチルアミノ基など）、ヒ
ドロキシ基、ニトロ基、シアムＬカルボキシル基などが
あげられる。A is a divalent aromatic hydrocarbon group such as 0-phenylene, 0-naphthylene group, 1゜2-anthraquinonylene group, 9.10-phenanthrylene group, 3゜4-pyrazoldiyl group, 2.3- Heterocycle 2 such as pyridinediyl group, 4.5-pyrimidinediyl group, 6,7-indazolediyl group, 5.6-benzimidazole group, 6.7-chiradiyl group, etc.
Value groups can be mentioned. These may have substituents, such as alkyl groups (methyl, ethyl, propyl, butyl, etc.), alkoxy groups (methoxy, ethoxy, propoxy, butoxy, etc.), halogen atoms (fluorine atoms, etc.). , chlorine atom, bromine atom, etc.), alkylamino group (methylamino group, ethylamino group, etc.), dialkylamino group (dimethylamino group, diethylamino group, etc.), hydroxy group, nitro group, cyam L carboxyl group, etc. .
前記一般式［Ｉ］で示されるビスアゾ化合物（以降、本
発明のビスアゾ化合物と称する。）の具体例としては、
例えば次の構造式を有するものが挙げられるが、これに
よって本発明のビスアゾ化合物が限定されるものではな
い。Specific examples of the bisazo compound represented by the general formula [I] (hereinafter referred to as the bisazo compound of the present invention) include:
For example, compounds having the following structural formula may be mentioned, but the bisazo compounds of the present invention are not limited thereto.
以下余白１
！
以上の如きビスアゾ化合物は、公知の方法により容易に
合成することができる。1 margin below! The above bisazo compounds can be easily synthesized by known methods.
合成例（例示化合物（１）の合成）
２−（４−アミノフェニル） −５−（４−シアノ−β
−シアノスチリル）−１，３，４オキサゾール３．７９
ｇ（０，０１モル）を塩Ｍ１０１β、水２０１ｉ２に分
散し、５℃以下に保ちつつ亜硝酸ナトリウム１．４０１
Ｊ（０，０２モル）を水５１Ｑに溶した溶液を滴下した
。同温度でさらに１時間撹拌をつづけた後、不溶物を濾
過除去し、濾液に六弗化燐酸アンモニウム４．９ｇを水
５０１βに溶かした溶液を加えた。析出したテトラゾニ
ウム塩を濾取し、Ｎ、Ｎ−ジメチルホルムアミド（ＤＭ
Ｆ） １００ｉＲに溶解した。５℃以下に保ちながら
、２−ヒドロキシ−３−ナフトエ酸−アニリド５．２６
１；ｌ（０，０２モル）を０ＭＦ２０ｈ（２に溶かした
溶液を滴下した。Synthesis example (synthesis of exemplified compound (1)) 2-(4-aminophenyl)-5-(4-cyano-β
-cyanostyryl)-1,3,4oxazole 3.79
Disperse g (0.01 mol) in salt M101β and water 201i2, and add 1.401 mol of sodium nitrite while keeping the temperature below 5°C.
A solution of J (0.02 mol) dissolved in water 51Q was added dropwise. After continuing stirring at the same temperature for an additional hour, insoluble matter was removed by filtration, and a solution of 4.9 g of ammonium hexafluorophosphate dissolved in 501β of water was added to the filtrate. The precipitated tetrazonium salt was collected by filtration and treated with N,N-dimethylformamide (DM
F) Dissolved at 100iR. 2-Hydroxy-3-naphthoic acid-anilide 5.26 while keeping the temperature below 5°C.
A solution of 1:1 (0.02 mol) dissolved in 0MF20h (2) was added dropwise.
ひきつづき５℃以下に保ちながらトリエタノールアミン
６１１１ （０，０４モル）をＤ Ｍ Ｆ ３０ ｖ
（ｌに溶解したものを滴下し、５℃以下で１時間、室温
で４時間撹拌した。反応後析出晶を濾取し、ＤＭＦ洗浄
、水洗浄して乾燥し、目的物７゜９ｇを得た。Triethanolamine 6111 (0.04 mol) was added to DMF 30 v while keeping the temperature below 5°C.
After the reaction, the precipitated crystals were collected by filtration, washed with DMF, washed with water, and dried to obtain 7.9 g of the desired product. Ta.
本発明のビスアゾ化合物は優れた光導電性を有し、これ
を用いて電子写真感光体を製造する場合、導電性支持体
上に本発明のビスアゾ化合物をパイ 。The bisazo compound of the present invention has excellent photoconductivity, and when an electrophotographic photoreceptor is manufactured using the same, the bisazo compound of the present invention is coated on a conductive support.
レダー中に分散した感光層を設けることにより製造する
ことができるが、本発明のビスアゾ化合物の持つ光導電
性のうち、特に優れたキャリア発生能を利用してキャリ
ア発生物質として用い、これと組合せて有効に作用し得
るキャリア輸送物質と共に用いることにより、いわゆる
機能分離型の感光体を構成した場合特に優れた結果が得
られる。It can be produced by providing a photosensitive layer dispersed in a radar, but among the photoconductivity of the bisazo compound of the present invention, it is used as a carrier-generating substance by taking advantage of its particularly excellent carrier-generating ability, and is used in combination with this. Particularly excellent results can be obtained when a so-called functionally separated type photoreceptor is constructed by using it together with a carrier transporting substance that can effectively act as a carrier transport material.
前記機能分離型感光体は前記両物質の混合分散型のもの
であってもよいが、キャリア発生物質を含むキャリア発
生層とキャリア輸送物質を含むキャリア輸送層を積層し
た積層型感光体とすることがより好ましい。The functionally separated type photoreceptor may be a mixed and dispersed type of both of the above substances, but it may be a laminated type photoreceptor in which a carrier generation layer containing a carrier generation substance and a carrier transport layer containing a carrier transport substance are laminated. is more preferable.
本発明のビスアゾ化合物をキャリア発生物質として用い
た場合、これと組合せて用いられるキャリア輸送物質と
しては、特に制限はないが、例えばオキサゾール誘導体
、オキサジアゾール誘導体、チ、アゾール誘導体、チア
ジアゾール誘導体、トリアゾール誘導体、イミダゾール
誘導体、イミダシロン誘導体、イミダゾリジン誘導体、
ビスイミダ −シリジン誘導体、スチリル化合物、ヒド
ラゾン化合物、ピラゾリン誘導体、アミン誘導体、オキ
ナシロン誘導体、ベンゾチアゾール誘導体、ベンズイミ
ダゾール誘導体、キナゾリン誘導体、ベンゾフラン誘導
体、アクリジン誘導体、）Ｉナジン誘導体、アミノスチ
ルベン誘導体、ポリ−Ｎ−ビニルカルバゾール、ポリ−
１−ビニルピレン、ポリ−９−ビニルアントラゼン等で
ある。When the bisazo compound of the present invention is used as a carrier-generating substance, there are no particular restrictions on the carrier-transporting substance that can be used in combination with it, but examples include oxazole derivatives, oxadiazole derivatives, thiazole derivatives, thiadiazole derivatives, and triazole derivatives. derivatives, imidazole derivatives, imidacilone derivatives, imidazolidine derivatives,
Bisimida-silidine derivatives, styryl compounds, hydrazone compounds, pyrazoline derivatives, amine derivatives, oquinacylone derivatives, benzothiazole derivatives, benzimidazole derivatives, quinazoline derivatives, benzofuran derivatives, acridine derivatives, )I nadine derivatives, aminostilbene derivatives, poly-N- vinyl carbazole, poly-
These include 1-vinylpyrene and poly-9-vinylanthrazene.
本発明において用いられるキャリア輸送物質としては光
照射時発生ずるホールの支持体側への輸送能力が優れて
いる外、前記本発明のビスアゾ化合物との組合ゼに好適
なものが好ましく用いられ、かかるキャリア輸送物質と
して好ましいものは、下記一般式（Ａ）、（Ｂ）及び（
Ｃ）で表わされるものが挙げられる。The carrier transport substance used in the present invention is preferably one that has an excellent ability to transport holes generated during light irradiation to the support side, and is also suitable for combination with the bisazo compound of the present invention. Preferred transport substances are the following general formulas (A), (B) and (
Examples include those represented by C).
但し、Ａ「１、Ａｒ２、Ａｒ４はそれ−ＦｔＬ置換又は
未置換のアリール基を表わし、Ａｒ３は置換又は未置換
のアリーレン基を表わし、Ｒ１は水素原子、置換若しく
は未置換のアルキル基、又は置換もしくは未置換のアリ
ール基を表わす。However, A'1, Ar2, Ar4 represent a substituted or unsubstituted aryl group, Ar3 represents a substituted or unsubstituted arylene group, and R1 is a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted Or it represents an unsubstituted aryl group.
このような化合物の具体例は特開昭５８−６５４４０号
の第３〜４頁及び同５８−１９８０４３号の第３〜６頁
に詳細に記載されている。Specific examples of such compounds are described in detail on pages 3 to 4 of JP-A-58-65440 and pages 3-6 of JP-A-58-198043.
Ｋ： 但し、Ｒ１は置換、未置換のアリール基、置換。K: However, R1 is a substituted or unsubstituted aryl group, or a substituted.
未置換の複素１１Ｗ基であり、Ｒ２は水素原子、置換。It is an unsubstituted hetero 11W group, and R2 is a hydrogen atom, substituted.
未置換のアルキル基、置換、未置換のアリール基を表わ
し、詳細には特開昭５８−１３４６４２＠及び同５８−
１６６３５４号の公報に記載されている。It represents an unsubstituted alkyl group, a substituted or unsubstituted aryl group, and in detail, it is described in JP-A-58-134642@ and JP-A-58-134642.
It is described in the publication No. 166354.
一般式（Ｃ）
但し、Ｒ１は置換、未置換のアリール基であり、Ｒ２は
水素原子、ハロゲン原子、置換、未置換のアルキル基、
置換、未置換のアルコキシ基、置換。General formula (C) However, R1 is a substituted or unsubstituted aryl group, and R2 is a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group,
Substituted, unsubstituted alkoxy group, substituted.
未置換のアミノ基、ヒドロキシ基であり、Ｒ３は置換、
未置換のアリール基、置換、未置換の複素ｍＭを表わす
。これらの化合物の合成法及びその例示は特公昭５７−
１４８７５０号公報に詳細に記載されており、本発明に
援用することができる。unsubstituted amino group, hydroxy group, R3 is substituted,
Represents an unsubstituted aryl group, substituted, or unsubstituted complex mM. Synthesis methods and examples of these compounds are given in Japanese Patent Publication No. 57-
It is described in detail in Japanese Patent No. 148750, and can be incorporated into the present invention.
本発明のその他の好ましいキャリア輸送物質としては、
特開昭５７−６７９４０号、同５９−１５２５２号、同
５７−１０１８４４号公報にそれぞれ記載されているヒ
ドラゾン化合物を挙げることができる。Other preferred carrier transport materials of the present invention include:
Examples include hydrazone compounds described in JP-A-57-67940, JP-A-59-15252, and JP-A-57-101844, respectively.
電子写真感光体の構成は種々の形態が知られているが、
本発明の電子写真感光体はそれらのいずれの形態をもと
り得る。Various configurations of electrophotographic photoreceptors are known, but
The electrophotographic photoreceptor of the present invention can take any of these forms.
通常は、第１図〜第６図の形態である。第１図及び第２
図では、導電性支持体１上に前述のビスアゾ化合物を主
成分とするキャリア発生層２と、キャリア輸送物質を主
成分として含有するキャリア輸送Ｎ３との積層体より成
る感光層４を設ける。Usually, the configuration is as shown in FIGS. 1 to 6. Figures 1 and 2
In the figure, a photosensitive layer 4 made of a laminate of a carrier generation layer 2 containing the above-mentioned bisazo compound as a main component and a carrier transport N3 containing a carrier transport substance as a main component is provided on a conductive support 1.
第３図及び第４図に示すようにこの感光Ｗ１４は、導電
性支持体上に設けた中間層５を介して設けてもよい。こ
のように感光層４を二層構成としたときに最も優れた電
子写真特性を有する感光体が得られる。また本発明にお
いては、第５図および第６図に示すように前記キャリア
発生物質７をキャリア輸送物質を主成分とする１１６中
に分散せしめて成る感光層４を導電性支持体１上に直接
、あるいは中間ｇ！５を介して設けてもよい。また本発
明においては、最外層として保護層を設けてもよい。As shown in FIGS. 3 and 4, this photosensitive material W14 may be provided via an intermediate layer 5 provided on the conductive support. When the photosensitive layer 4 has a two-layer structure in this manner, a photoreceptor having the most excellent electrophotographic properties can be obtained. Further, in the present invention, as shown in FIGS. 5 and 6, a photosensitive layer 4 formed by dispersing the carrier-generating substance 7 in a carrier-transporting substance 116 as a main component is directly deposited on the conductive support 1. , or intermediate g! 5 may be provided. Further, in the present invention, a protective layer may be provided as the outermost layer.
二層構成の感光層４を構成するキャリア発生層２は導電
性支持体１、もしくはキャリア輸送ｊｌｓ上に直接、あ
るいは必要に応じて接＠層もしくはパリヤシなどの中間
層５を設けた上に例えば次の方法によって形成すること
ができる。The carrier generation layer 2 constituting the photosensitive layer 4 having a two-layer structure can be formed directly on the conductive support 1 or the carrier transport layer, or on an intermediate layer 5 such as a contact layer or a layer as required, for example. It can be formed by the following method.
Ｍ−１）ビスアゾ化合物を適当な溶媒に溶解した溶液を
、あるいは必要に応じてバインダー樹脂を加え混合溶解
した溶液を塗布する方法。M-1) A method of applying a solution in which a bisazo compound is dissolved in a suitable solvent, or a solution in which a binder resin is mixed and dissolved, if necessary.
Ｍ−２）ビスアゾ化合物をボールミル、ホモミキサ等に
よって分散媒中で微細粒子（好ましくは粒径５μｍ以下
、更に好ましくは１μＩＱ下）とし、必要に応じてバイ
ンダー樹脂を加え混合分散した分散液を塗布する方法。M-2) Make the bisazo compound into fine particles (preferably particle size of 5 μm or less, more preferably 1 μIQ or less) in a dispersion medium using a ball mill, homomixer, etc., add a binder resin as necessary, and apply the mixed and dispersed dispersion. Method.
キャリア発生層の形成に使用される溶媒あるいは分散媒
としては、ｎ−ブチルアミン、ジエチルアミン、エチレ
ンジアミン、イソプロパツールアミン、トリエタノール
アミン、トリエチレンジアミン、Ｎ、Ｎ−ジメチルホル
ムアミド、アセトン、メチルエチルケトン、シクロヘキ
サノン、ベンゼン、トルエン、キシレン、クロロホルム
、１．２−ジクロロエタン、１，２−ジクロロメン、１
．１．２−トリクロロエタン、１．１．１−トリクロロ
エタン、トリ、クロロエチレン、テトラクロ０エタン、
ジクロロメタン、テトラヒドロフラン、ジオキサン、メ
タノール、エタノール、イソプロパツール、酢酸エチル
、酢酸ブチル、ジメチルスルホキシド、メチルセロソル
ブ等が挙げられる。Solvents or dispersion media used to form the carrier generation layer include n-butylamine, diethylamine, ethylenediamine, isopropanolamine, triethanolamine, triethylenediamine, N,N-dimethylformamide, acetone, methylethylketone, cyclohexanone, and benzene. , toluene, xylene, chloroform, 1,2-dichloroethane, 1,2-dichloromene, 1
．． 1.2-trichloroethane, 1.1.1-trichloroethane, trichloroethylene, tetrachloroethane,
Examples include dichloromethane, tetrahydrofuran, dioxane, methanol, ethanol, isopropanol, ethyl acetate, butyl acetate, dimethyl sulfoxide, methyl cellosolve, and the like.
また、キャリア輸送層は上記キャリア発生層と同様にし
て形成することができる。Further, the carrier transport layer can be formed in the same manner as the carrier generation layer described above.
キャリア発生層あるいはキャリア輸送層の形成に用いら
れるバインダー樹脂は任意のものを用いることができる
が、疎水性で、かつ誘電率が高く、電気絶縁性のフィル
ム形成性高分子重合体を用いるのが好ましい。このよう
な高分子重合体としては、例えば次のものを挙げること
ができるが、これらに限定されるものではない。Any binder resin can be used to form the carrier generation layer or the carrier transport layer, but it is preferable to use a film-forming polymer that is hydrophobic, has a high dielectric constant, and is electrically insulating. preferable. Examples of such high molecular weight polymers include, but are not limited to, the following.
Ｐ−１）ポリカーボネート
Ｐ−２）ポリエステル
Ｐ−３）メタクリル酸
Ｐ−４）アクリル樹脂
Ｐ−５）ポリ塩化ビニル
Ｐ−６）ポリ塩化ビニリデン
Ｐ−７）ポリスチレン
Ｐ−８）ポリビニルアセテート
Ｐ−９）スチレン−ブタジェン共重合体Ｐ −１０）塩
化ビニリデン−アクリ０ニトリル共重合体
Ｐ−１１）塩化ビニル−酢酸ビニル共重合体Ｐ −１２
）塩化ビニル−酢酸ビニル−無水マレイン酸共重合体
Ｐ −１３）シリコン樹脂
Ｐ −１４）シリコン−アルキッド樹脂Ｐ −１５＞フ
ェノールホルムアルデヒド樹脂Ｐ −１６）スチレン−
アルキッド樹脂Ｐ −１７）ポリ−Ｎ−ビニルカルバゾ
ールＰ −１８）ポリビニルブチラール
Ｐ −１９）ポリビニルフォルマール
これらのバインダー樹脂は、単独であるいは２種以上の
混合物として用いることができる。P-1) Polycarbonate P-2) Polyester P-3) Methacrylic acid P-4) Acrylic resin P-5) Polyvinyl chloride P-6) Polyvinylidene chloride P-7) Polystyrene P-8) Polyvinyl acetate P-9 ) Styrene-butadiene copolymer P-10) Vinylidene chloride-acrylic nitrile copolymer P-11) Vinyl chloride-vinyl acetate copolymer P-12
) Vinyl chloride-vinyl acetate-maleic anhydride copolymer P -13) Silicone resin P -14) Silicone-alkyd resin P -15> Phenol formaldehyde resin P -16) Styrene -
Alkyd resin P-17) Poly-N-vinylcarbazole P-18) Polyvinyl butyral P-19) Polyvinyl formal These binder resins can be used alone or in a mixture of two or more.
本発明の感光体が積層型構成の場合、キャリア発生層中
のバインダー：キャリア発生物質：キャリア輸送物質の
重量比は好ましくはＯ〜１０Ｇ ：１〜ｓｏｏ： ｏ
〜５００である。When the photoreceptor of the present invention has a laminated structure, the weight ratio of binder:carrier generating substance:carrier transporting substance in the carrier generating layer is preferably O to 10G:1 to soo:o.
~500.
キャリア発生物質の含有割合がこれより少ないと光感度
が低く、残留電位の増加を招き、またこれより多いと暗
減衰及び受容電位が低下する。If the content of the carrier-generating substance is less than this, the photosensitivity will be low and the residual potential will increase, and if it is more than this, the dark decay and acceptance potential will decrease.
また、キャリア輸送物質はキャリア輸送層中のバインダ
ー樹脂１００重量部当り２０〜２００重量部が好ましく
、特に好ましくは３０〜１５０重量部である。Further, the amount of the carrier transport substance is preferably 20 to 200 parts by weight, particularly preferably 30 to 150 parts by weight, per 100 parts by weight of the binder resin in the carrier transport layer.
以上のようにして形成されるキャリア発生層の膜厚は、
好ましくは０．０１〜１０μ霧、特に好ましくは０．１
〜５μｍである。The thickness of the carrier generation layer formed as described above is
Preferably 0.01-10μ mist, particularly preferably 0.1
~5 μm.
また、形成されるキャリア輸送層の膜厚は、好ましくは
５〜５０μｍ、特に好ましくは５〜３０μ■である。Further, the thickness of the carrier transport layer to be formed is preferably 5 to 50 μm, particularly preferably 5 to 30 μm.
一方、本発明の感光体が単ａｎ能分離型構成の場合、感
光層中のバインダー：キャリア発生物質：キャリア輸送
物質の重量比は０〜１００： １〜ＳＯＯ：１〜５０
０が好ましく、形成される感光層の膜厚は５〜５０μｍ
が好ましく、特に好ましくは５〜３０Ｉｉ翔である。On the other hand, when the photoreceptor of the present invention has a single annular functional separation type structure, the weight ratio of binder: carrier generating substance: carrier transporting substance in the photosensitive layer is 0 to 100: 1 to SOO: 1 to 50.
0 is preferable, and the thickness of the photosensitive layer to be formed is 5 to 50 μm.
is preferable, and particularly preferably 5 to 30 Ii.
本発明の電子写真感光体に用いられる導電性支持体とし
ては、合金を含めた金属板、金属ドラムまたは導電性ポ
リマー、酸化インジウム等の導電性化合物や合金を含め
たアルミニウム、パラジウム、金等の金ｊｉｉｌｆｆｔ
を塗布、蒸着あるいはラミネートして、導電性化された
紙、プラスチックフィルム等が挙げられる。接着層ある
いはパリｔ７ＩＩｉなどの中間層としては、前記バイン
ダー樹脂として用いられる高分子重合体のほか、ポリビ
ニルアルコール、エチルセルロ−ス
ロース
ニウムなどが用いられる。The conductive support used in the electrophotographic photoreceptor of the present invention is a metal plate including an alloy, a metal drum or a conductive polymer, a conductive compound such as indium oxide, aluminum including an alloy, palladium, gold, etc. gold jiilfft
Paper, plastic films, etc. made conductive by coating, vapor-depositing, or laminating are examples. For the adhesive layer or intermediate layer such as Pari-t7IIi, polyvinyl alcohol, ethyl cellulose, and the like can be used in addition to the polymer used as the binder resin.
本発明の感光層にはキャリア発生物質のキャリア発生機
能を改善する目的で有機アミン類を添加することができ
、特に２級アミンを添加するのが好ましい。Organic amines can be added to the photosensitive layer of the present invention for the purpose of improving the carrier-generating function of the carrier-generating substance, and it is particularly preferable to add a secondary amine.
かかる２級アミンとしては、例えばジメチルアミン、ジ
エチルアミン、ジ−ｎプロピルアミン、ジ−イソプロピ
ルアミン、ジ−ｎブチルアミン、ジ−イソブチルアミン
、ジ−ｎアミルアミン、ジ−イソアミルアミン、ジ−ｎ
ヘキシルアミン、ジ−イソヘキシルアミン、ジ−ｎペン
チルアミン、ジ−イソペンチルアミン、ジ−ｎオクチル
アミン、ジ−イソオクチルアミン、ジ−ｎノニルアミン
、ジ−イソノニルアミン、ジ−ｎデシルアミン、ジ−イ
ソデシルアミン、ジ−ｎモノデシルアミン、ジ−イソモ
ノデシルアミン、ジ−ｎドデシルアミン、ジ−イソドデ
シルアミン等を挙げることができる。Such secondary amines include, for example, dimethylamine, diethylamine, di-n propylamine, di-isopropylamine, di-n butylamine, di-isobutylamine, di-n amylamine, di-isoamylamine, di-n
Hexylamine, di-isohexylamine, di-n-pentylamine, di-isopentylamine, di-n-octylamine, di-isooctylamine, di-n-nonylamine, di-isononylamine, di-n-decylamine, di- -isodecylamine, di-n-monodecylamine, di-isomonodecylamine, di-n-dodecylamine, di-isododecylamine, and the like.
又かかる有機アミン類の添加ｍとしては、キャリア発生
物質の１倍以下、好ましくは０．２倍〜０、００５倍の
範囲のモル数とするのがよい。The molar amount of the organic amine added is preferably 1 times or less, preferably 0.2 times to 0.005 times the amount of the carrier generating substance.
又、本発明の感光層には、オゾン劣化防止の目的で酸化
防止剤を添加することができる。Further, an antioxidant can be added to the photosensitive layer of the present invention for the purpose of preventing ozone deterioration.
かかる酸化防止剤の代表的具体例を以下に示すが、これ
に限定されるものではない。Typical examples of such antioxidants are shown below, but the invention is not limited thereto.
（Ｉ）群：ヒンダードフェノール類 ！ジブチルヒトＯ
キシトルエン、２．２′−メチレンビス（６−１−ブチ
ル−４−メチルフェノール）、４．４’−ブチリデンビ
ス（６−１−ブチル−３−メチルフェノール）、４．４
’ −チオビス（６−ｔ−ブチル−３−メチルフェノー
ル）、２．２′−ブチリデンビス（６−【−ブチル−４
−メチルフェノール）、α−トコフェロール、β−１−
コフェロール、２，２．４−トリメチル−６−ヒトロキ
シー７−ｔ−ブチルクロマン、ペンタエリスチルテトラ
キス［３−（３，５−ジーｔ−ブ°チルー４−ヒトＯキ
シフェニル）プロピオネート１，２．２’−チオジエチ
レンビス［３−（３゜５−ジ−ｔ−ブチル−４−ヒドロ
キシフェニル）プロピオネート］、１．６−ヘキサンジ
オールビス［３−（３，５−ジ−ｔ−ブチル−４−ヒド
ロキシフェニル）プロピオネート］、ブチルヒドロキシ
アニソール、ジブチルヒドロキシアニソール、１− ［
２−（（３，５−ジーｔｅｒｔ−ブチルー４−ヒドＯキ
シフェニル）プロピオニルオキシ）エチル］ −４−（
３−（３，５−ジーｔａｒｔ−ブチルー４−ヒドロキシ
フェニル）プロピオニルオキシ１−２．２．６．６−テ
トラメチルビペリジルなど。Group (I): Hindered phenols! dibutyl human O
Xytoluene, 2.2'-methylenebis(6-1-butyl-4-methylphenol), 4.4'-butylidenebis(6-1-butyl-3-methylphenol), 4.4
'-thiobis(6-t-butyl-3-methylphenol), 2,2'-butylidenebis(6-[-butyl-4
-methylphenol), α-tocopherol, β-1-
Copherol, 2,2,4-trimethyl-6-hydroxy-7-t-butylchroman, pentaerythyltetrakis [3-(3,5-di-t-butyl-4-human-Oxyphenyl)propionate 1,2. 2'-thiodiethylenebis[3-(3゜5-di-t-butyl-4-hydroxyphenyl)propionate], 1,6-hexanediolbis[3-(3,5-di-t-butyl-4) -hydroxyphenyl)propionate], butylhydroxyanisole, dibutylhydroxyanisole, 1-[
2-((3,5-di-tert-butyl-4-hydrooxyphenyl)propionyloxy)ethyl] -4-(
3-(3,5-di-tart-butyl-4-hydroxyphenyl)propionyloxy 1-2.2.6.6-tetramethylbiperidyl and the like.
（Ｉｆ）群：パラフエニレンジアミン類Ｎ−フェニル−
Ｎ′−イソプロピル−ｐ−フェニレンジアミン、Ｎ、Ｎ
’−ジー５ｅｃ−ブチル−ｐ−フェニレンジアミン、Ｎ
−フェニル−Ｎ−３ｅＣ−ブチル−ｐ−フェニレンジア
ミン、Ｎ。(If) group: paraphenylenediamines N-phenyl-
N'-isopropyl-p-phenylenediamine, N,N
'-5ec-butyl-p-phenylenediamine, N
-Phenyl-N-3eC-butyl-p-phenylenediamine, N.
Ｎ′−ジイソプロピル−ｐ−フェニレンジアミン、Ｎ、
Ｎ’−ジメチル−Ｎ、Ｎ’−ジ−ｔ−ブチル−ｐ−フェ
ニレンジアミンなど。N'-diisopropyl-p-phenylenediamine, N,
N'-dimethyl-N, N'-di-t-butyl-p-phenylenediamine, etc.
（ＩＩＩ）群：ハイドロキノン類
２．５−ジー【−オクチルハイドロキノン、２゜６−シ
ドデシルハイドロキノン、２−ドデシルハイドロキノン
、２−ドデシル−５−クロロハイドロキノン、２−ｔ−
オクチル−５−メチルハイドロキノン、２−（２−オク
タデセニル）−５−メチルハイドロキノンなど。Group (III): Hydroquinones 2.5-di[-octylhydroquinone, 2゜6-sidedecylhydroquinone, 2-dodecylhydroquinone, 2-dodecyl-5-chlorohydroquinone, 2-t-
Octyl-5-methylhydroquinone, 2-(2-octadecenyl)-5-methylhydroquinone, etc.
（ＩＶ）群：有機硫黄化合物類
ジラウリル−３，３′−チオジプロピオネート、ジステ
アリル−３，３′−チオジプロピオネート、ジテトラデ
シルー３．３′−チオジプロピオネートなど。Group (IV): organic sulfur compounds dilauryl-3,3'-thiodipropionate, distearyl-3,3'-thiodipropionate, ditetradecyl-3,3'-thiodipropionate, etc.
（Ｖ）群：有機硫黄化合物類
トリフェニルホスフィン、トリ（ノニルフェニル）ホス
フィン、トリ（ジノニルフェニル）ホスフィン、トリク
レジルホスフィン、トリ（２，４−ジブチルフェノキシ
）ホスフィンなど。Group (V): organic sulfur compounds triphenylphosphine, tri(nonylphenyl)phosphine, tri(dinonylphenyl)phosphine, tricresylphosphine, tri(2,4-dibutylphenoxy)phosphine, etc.
これらの化合物はゴム、プラスデック、油脂類等の酸化
防止剤として知られており、市販品を容易に入手できる
。These compounds are known as antioxidants for rubber, Plusdec, oils and fats, and are easily available commercially.
これらの酸化防止剤はキャリア発生層、キャリア輸送層
、又は保護層のいずれに添加されてもよいが、好ましく
はキャリア輸送層に添加される。These antioxidants may be added to any of the carrier generation layer, carrier transport layer, or protective layer, but are preferably added to the carrier transport layer.
その場合の酸化防止剤の添加但はキャリア輸送物質１０
０重通部に対して０．１〜１００重量部、好ましくは１
〜５０重１部、特に好ましくは５〜２５重量部である。In that case, the addition of an antioxidant is required, but the carrier transport substance must be 10%
0.1 to 100 parts by weight, preferably 1
~50 parts by weight, particularly preferably 5 to 25 parts by weight.
本発明においてキャリア発生層には感度の向上、残留電
位乃至反復使用時の疲労低減等を目的として、一種又は
二種以上の電子受容性物質を含有せしめることができる
。In the present invention, the carrier generation layer may contain one or more electron-accepting substances for the purpose of improving sensitivity, reducing residual potential or fatigue during repeated use, etc.
ここに用いることのできる電子受容性物質としては、例
えば、無水コハク酸、無水マレイン酸、ジブロム無水マ
レイン酸、無水フタル酸、テトラクロル無水フタル酸、
テトラブロム無水フタル酸、３−ニトロ無水フタル酸、
４−ニトロ無水フタル酸、無水ビＯメリット酸、無水メ
リット酸、テトラシアノエチレン、テトラシアノキノジ
メタン、Ｏ−ジニトロベンゼン、ｍ−ジニトロベンゼン
、１．３．５−トリニトロベンゼン、パラニドｏベンゾ
ニトリル、ビクリルクロライド、キノンクロルイミド、
クロラニル、プルマニル、ジクロロジシアノバラベンゾ
キノン、アントラキノン、ジニトロアントラキノン、２
．７−ジニトロフルオレノン、２．４．７−トリニトロ
フルオレノン、２゜４．５．７−テトラニトロフルオレ
ノン、９−フルオレニリデン［ジシアノメチレンマロノ
ジニトリル］、ポリニトロ−９−フルオレニリデン−［
ジシアノメチレンマロノジニトリル］、ピクリン酸、０
−ニトロ安息香酸、ｐ−ニトロ安息香酸、３．５−ジニ
トロ安息香酸、ペンタフルオロ安息香酸、５−二１〜ロ
サリチル酸、３．５−ジニトロサリチル酸、フタル酸、
メリット酸、その他の電子親和力の大きい化合物を挙げ
ることができる。Examples of electron-accepting substances that can be used here include succinic anhydride, maleic anhydride, dibromaleic anhydride, phthalic anhydride, tetrachlorophthalic anhydride,
Tetrabromo phthalic anhydride, 3-nitro phthalic anhydride,
4-Nitro-phthalic anhydride, bi-O-mellitic anhydride, mellitic anhydride, tetracyanoethylene, tetracyanoquinodimethane, O-dinitrobenzene, m-dinitrobenzene, 1.3.5-trinitrobenzene, paranido-obenzonitrile , vicryl chloride, quinone chlorimide,
Chloranil, pullmanil, dichlorodicyanobarabenzoquinone, anthraquinone, dinitroanthraquinone, 2
．． 7-dinitrofluorenone, 2.4.7-trinitrofluorenone, 2゜4.5.7-tetranitrofluorenone, 9-fluorenylidene [dicyanomethylenemalonodinitrile], polynitro-9-fluorenylidene-[
dicyanomethylenemalonodinitrile], picric acid, 0
-Nitrobenzoic acid, p-nitrobenzoic acid, 3.5-dinitrobenzoic acid, pentafluorobenzoic acid, 5-21-rosalicylic acid, 3.5-dinitrosalicylic acid, phthalic acid,
Examples include mellitic acid and other compounds with high electron affinity.
電子受容性物質の添加量は、重量比でキャリア発生物質
：電子受容性物質−１００： ０．０１〜２００１好
ましくは１００： ０．１〜１００である。The amount of the electron-accepting substance added is carrier-generating substance:electron-accepting substance-100:0.01-2001 in weight ratio, preferably 100:0.1-100.
電子受容性物質はキャリア輸送層に添加してもよい。か
かる層への電子受容性物質の添加量は重量比でキャリア
輸送物質：Ｎ子嚢容性物質−ｉ’ｏｏ ：０．０１〜１
００１好ましくは１００： ０．１〜５０である。The electron-accepting substance may be added to the carrier transport layer. The amount of electron-accepting substance added to this layer is carrier transporting substance:N ascus-accommodating substance-i'oo:0.01 to 1 by weight.
001 preferably 100:0.1-50.
また本発明の感光体には、その他、必要により感光層を
保護する目的で紫外線吸収剤等を含有してもよく、また
感色性補正の染料を含有してもよゝい。In addition, the photoreceptor of the present invention may also contain, if necessary, an ultraviolet absorber or the like for the purpose of protecting the photosensitive layer, and may also contain a dye for color sensitivity correction.
本発明の電子写真感光体は以上のような構成であって、
後述する実施例からも明らかなように、帯電特性、感度
特性、画保形成特性に優れており、特に繰返し使用した
ときにも疲労劣化が少なく、耐用性が優れたものである
。The electrophotographic photoreceptor of the present invention has the above structure,
As is clear from the Examples described below, it has excellent charging characteristics, sensitivity characteristics, and image support forming characteristics, and especially shows little fatigue deterioration even when used repeatedly, and has excellent durability.
更に本発明の電子写真感光体は電子写真複写機のほか、
レーザー、ブラウン管（ＣＲＴ）、発光ダイオード（Ｌ
ＥＤ）を光源とするプリンターの感光体などの応用分野
、にも広く用いることができる。Furthermore, the electrophotographic photoreceptor of the present invention can be used in electrophotographic copying machines, as well as
Laser, cathode ray tube (CRT), light emitting diode (L
It can also be widely used in applied fields such as photoreceptors for printers that use ED) as a light source.
［実施例］
以下、本発明を実施例によって具体的に説明するが、こ
れにより本発明の実施態様が限定されるものではない。[Examples] Hereinafter, the present invention will be specifically explained using Examples, but the embodiments of the present invention are not limited thereby.
実施例１
ポリエステルフィルム上にアルミニウム箔をラミネート
シて成るＳ電性支持体上に、塩化ビニル−酢酸ビニル−
無水マレイン酸共同合体［エスレックＭＦ−１０Ｊ （
活水化学社製）よりなる厚さ０．０５μｍの中間層を設
け、その上に例示化合物Ｎｏ、４０の２ｏとポリカーボ
ネ−１・樹脂「パンライ）−Ｌ −１２５０Ｊ （余
人化成社製）２ａとを１．２−ジクｏｏエタン１１（ｈ
ｆｆｉに加え、ボールミルで１２時間分散した。この分
散液を乾燥時の膜厚が０．５μ霞になるように塗布し、
キャリア発生層とし、更にその上に、キャリア輸送物質
として、下記構造式（Ｋ−１）６０をポリカーボネート
樹脂「パンライトＬ−１２５０Ｊ １００とを１．２−
ジクロロエタン８０戴に溶解した液を乾燥後の膜厚が１
５μｍになるように塗布して、キャリア輸送層を形成し
、本発明の感光体を作製した。Example 1 Vinyl chloride-vinyl acetate-
Maleic anhydride copolymer [S-LEC MF-10J (
An intermediate layer with a thickness of 0.05 μm was provided, and exemplified compound No. 40-2O and polycarbonate 1/resin "Panrai"-L-1250J (manufactured by Yojin Kasei Co., Ltd.) 2a were provided on top of the intermediate layer. 1.2-dikuooethane 11(h
ffi and dispersed in a ball mill for 12 hours. This dispersion was applied so that the dry film thickness was 0.5 μm,
A carrier generation layer was formed, and a carrier transport material was formed on the polycarbonate resin "Panlite L-1250J 100" with the following structural formula (K-1) 60.
The film thickness after drying the solution dissolved in 80% dichloroethane is 1.
A carrier transport layer was formed by coating to a thickness of 5 μm, and a photoreceptor of the present invention was manufactured.
（Ｋ−１）
以上のようにして１ｑられた感光体を■川口電機製作所
製３ ｐ −４２８型静電紙試験機を用いて、以下の特
性評価を行った。帯電圧−６ｋｖで５秒間帯電した後、
５秒間暗放置し、次いで感光体表面での照度が３５ ｌ
ｕｘになるようにハロゲンランプ光を照射して、表面電
位を半分に減衰させるのに要する露光ｆｆ１（半減露光
Ｊｌ）Ｅ１／２を求めた。また３ ０ ｌｕｘ −ｓｅ
ｃの露光量で露光した後の表面電位（残留電位）ＶＲを
求めた。更に同様の測定を１００口繰返して行った。結
果は第１表に示す通りである。(K-1) The photoreceptor prepared as described above was subjected to the following characteristic evaluation using a 3P-428 type electrostatic paper tester manufactured by Kawaguchi Electric Seisakusho. After being charged for 5 seconds at a charging voltage of -6kV,
Leave it in the dark for 5 seconds, then reduce the illuminance on the photoreceptor surface to 35 l.
Exposure ff1 (half-reduced exposure Jl) E1/2 required to attenuate the surface potential by half was determined by irradiating halogen lamp light so as to obtain ux. Also 30 lux -se
The surface potential (residual potential) VR after exposure with an exposure amount of c was determined. Furthermore, the same measurement was repeated 100 times. The results are shown in Table 1.
比較例１
キャリア発生物質として下記ビスアゾ化合物（Ｇ−１）
を用いた他は、実施例１と同様にして比較用感光体を作
成した。Comparative Example 1 The following bisazo compound (G-1) was used as a carrier generating substance.
A comparative photoreceptor was prepared in the same manner as in Example 1, except that .
（Ｇ−１）
この比較用感光体について、実施例１と同様にして測定
を行ったところ、１１１表に示す結果を得た。(G-1) Regarding this comparative photoreceptor, measurements were performed in the same manner as in Example 1, and the results shown in Table 111 were obtained.
第１表
以上の結果から明らかなように、本発明の感光体は、比
較用感光体に比べ、感度、残留電位及び繰返しの安定性
において極めて優れたものである。As is clear from the results in Table 1 and above, the photoreceptor of the present invention is extremely superior in sensitivity, residual potential, and cyclic stability compared to the comparative photoreceptor.
実施例２〜１４
キャリア発生物質として、第２表に示した例示化合物を
用いたほかは、実施＠１と同様にして、本発明の感光体
を作成し、同様の測定を行なったところ第２表に示す結
果を得た。Examples 2 to 14 Photoreceptors of the present invention were prepared in the same manner as in Example @1, except that the exemplified compounds shown in Table 2 were used as carrier-generating substances, and the same measurements were performed. The results shown in the table were obtained.
第２表
実施例１５〜１７
キャリア発生物質として例示化合物Ｎ０１８．３０．７
９を夫々用い、キャリア輸送物質として、それぞれ下記
化合物を用い、その他は実施例１と同様にして、本発明
の感光体を作成し、同様の測定を行なったところ第３表
に示す結果を得た。Table 2 Examples 15 to 17 Exemplified compounds N018.30.7 as carrier generating substances
A photoreceptor of the present invention was prepared in the same manner as in Example 1, except that the following compounds were used as carrier transport substances, respectively, and the same measurements were performed. The results shown in Table 3 were obtained. Ta.
（Ｋ−２）
（Ｋ−３）
Ｃ＊ Ｈｓ
第３表
実施例１８
ポリエステルフィルム上にアルミニウムを蒸着した上に
実施例１で用いた中間層を設け、その上に例示化合物Ｎ
ｏ、４４の２ａとポリカーボネート樹脂「パンライトＬ
−１２５０Ｊ ２１７とを１，２−ジクロロエタン１
１０ｉＮに加えサンドグラインダーで８時間分散した。(K-2) (K-3) C* Hs Table 3 Example 18 Aluminum was vapor-deposited on a polyester film, the intermediate layer used in Example 1 was provided, and exemplified compound N
o, 44 2a and polycarbonate resin "Panlite L"
-1250J 217 and 1,2-dichloroethane 1
In addition to 10 iN, the mixture was dispersed for 8 hours using a sand grinder.
この分散液を乾燥時の膜厚が０．５μｍになるＪ：うに
塗布し、キ（シリア発生層とした。ざらにぞの上に、キ
ヤリア輸送物質として下記構造式（Ｋ−５）（ｌをポリ
カーボネート樹脂「パンライトに一１３００Ｊ （余人
化成社製）１０９とを１，２−ジクロロエタン８０顧に
溶解した液を乾燥後の膜厚が１５μｍになるように塗布
して、キャリア輸送層を形成し、本発明の感光体を作製
した。This dispersion was applied to a sea urchin with a dry film thickness of 0.5 μm to form a cyria generation layer.The following structural formula (K-5) (l A carrier transport layer was formed by coating polycarbonate resin "Panlite" with a solution prepared by dissolving 11300J (manufactured by Yojin Kasei Co., Ltd.) 109 in 1,2-dichloroethane 80% so that the film thickness after drying was 15 μm. Then, a photoreceptor of the present invention was manufactured.
（Ｋ−５）
この感光体について実施例１と同様の測定を行なったと
ころ第４表に示す結果になった。(K-5) The same measurements as in Example 1 were performed on this photoreceptor, and the results are shown in Table 4.
比較例２
キャリア発生物質として下記構造式（Ｇ−２＞で示され
るスチルベンアゾ顔料を用いた他は、実［１１８と同様
にして電子写真用感光体を作成した。この比較用感光体
について実施例１と同様の測定を行なったところ、第４
表に示ず結果を得た。Comparative Example 2 An electrophotographic photoreceptor was prepared in the same manner as in Example 118, except that a stilbene azo pigment represented by the following structural formula (G-2>) was used as a carrier-generating substance. When the same measurements as in Example 1 were made, the fourth
Results not shown in the table were obtained.
（Ｇ−２）
第４表
以上の結果から明らかなＪ：うに、本発明の感光体は、
比較用感光体に比べ、感度、残留電位及び繰返しの安定
性において極めて優れたものである。(G-2) It is clear from the results in Table 4 and above that J: Sea urchin, the photoreceptor of the present invention has
Compared to the comparative photoreceptor, it is extremely superior in sensitivity, residual potential, and repetition stability.
実施例１９〜２１
ポリエステルフィルム上にアルミニウム箔をラミネート
して成る導電性支持体上に、塩化ビニル−酢酸ビニル−
無水マレイン酸共重合体［エスレツクＭＦ−１０Ｊ
（活水化学社製）より成る厚さ０．０５μｌの中間層を
設け、その上に例示化合物ＮＯ，７６，２０どポリカー
ボネート樹脂［パンライトＬ −１２５０Ｊ ２０とを
テトラヒト０フラン１１０１１に加え、ボールミルで１
２時周分散した。この分散液を乾燥時の膜厚が０．５μ
ｍになるように塗布し、キャリア発生層とし、更にその
上に、キャリア輸送物質として、下記構造式（Ｋ−６，
に−７、に−８）で示される化合物の６σそれぞれとポ
リカーボネート樹脂ｒＺ−２００Ｊ（三菱ガス化学社製
）１０ｇとを１．２−ジクロロエタン８０顧に溶解した
液を乾燥後の膜厚が１５μ園になるように塗布して、キ
ャリア輸送層を形成し、本発明の感光体を作成した。Examples 19 to 21 Vinyl chloride-vinyl acetate-
Maleic anhydride copolymer [Eslec MF-10J
(manufactured by Katsusui Kagaku Co., Ltd.) with a thickness of 0.05 µl was provided, and on top of that, polycarbonate resin such as exemplified compound NO, 76, 20 [Panlite L-1250J 20] was added to Tetrahydrofuran 11011, and the mixture was heated in a ball mill. 1
Dispersed around 2 hours. The film thickness when this dispersion is dried is 0.5μ.
m to form a carrier generation layer, and on top of that, as a carrier transport substance, the following structural formula (K-6,
-7, -8) and 10g of polycarbonate resin rZ-200J (manufactured by Mitsubishi Gas Chemical Co., Ltd.) dissolved in 1,2-dichloroethane 80% to form a film with a film thickness of 15μ after drying. The photoreceptor of the present invention was prepared by coating the photoreceptor in a uniform manner to form a carrier transport layer.
（Ｋ−７）
（Ｋ −８）
実施例１と同様の測定を行なったところ第５表に示す結
果を得た。(K-7) (K-8) The same measurements as in Example 1 were performed, and the results shown in Table 5 were obtained.
第５表
実施例２２
直径６０■のアルミニウム製ドラムの表面に塩化ビニル
−酢酸ビニル−無水マレイン酸共重合体［エスレックＭ
Ｆ−１０Ｊ （Ｂ水化学社製）より成る厚さＯ，ＯＳμ
−の中間層を設け、その上に例示化合物ＮＯ，５，２（
Ｉとポリコニステル樹！１１［パイロン２００Ｊ （
東洋紡績社製）２９とを１．２−ジクロロエタン１１０
ｉ＆に混合し、ボールミル分散機で２４時間分散した分
散液を乾ｔ！Ａ後の膜厚が０．６μ■になるようにして
塗布し、キャリア発生層を形成した。Table 5 Example 22 Vinyl chloride-vinyl acetate-maleic anhydride copolymer [S-LEC M
Made of F-10J (manufactured by B Suikagaku Co., Ltd.), thickness O, OSμ
- is provided, and an intermediate layer of exemplified compound NO, 5, 2 (
I and the Polyconistel Tree! 11 [Pylon 200J (
Toyobo Co., Ltd.) 29 and 1,2-dichloroethane 110
The dispersion was mixed with i& and dispersed for 24 hours using a ball mill dispersion machine, and then dried. The film was coated so that the film thickness after A was 0.6 μm to form a carrier generation layer.
さらにこの上に、下記化合物（Ｋ−９）３０（＋とポリ
カーボネート樹Ｉｎ ｒニーピロンＳ−１０００Ｊ（三
菱ガス化学社製）５０（＋とを１，２−ジクロロエタン
４００１Ｑに溶解し、乾燥後の膜厚が１８μ謹になるよ
うに塗布してキャリア輸送層を形成し、ドラム状の感光
体を作成した。Furthermore, on top of this, the following compound (K-9) 30 (+) and polycarbonate resin Inr Kneepilon S-1000J (manufactured by Mitsubishi Gas Chemical Co., Ltd.) 50 (+) were dissolved in 1,2-dichloroethane 4001Q, and the film after drying was dissolved. A carrier transport layer was formed by coating to a thickness of 18 μm, and a drum-shaped photoreceptor was prepared.
（Ｋ−９）
このようにして作成した感光体を電子写真複写ＩＩ ｒ
Ｕ−Ｂｉｘ１５５０ＭＲＪ （コニカ株式会社製）の改
造機に装着し、画像を複写したところコントラス１−が
＾く、原画に忠実でかつ鮮明な複写画像を得た。また、
これは１０，０００回繰返しても変ることはなかった。(K-9) The photoreceptor thus prepared was electrophotographically copied II r.
When it was attached to a modified U-Bix1550MRJ (manufactured by Konica Corporation) and the image was copied, the contrast was low, and a clear copy image that was faithful to the original image was obtained. Also,
This did not change even after repeating this 10,000 times.
比較例３
キャリア元生物質として下記構造式（Ｇ−３）で表わさ
れるアゾ化合物に代えた他は、実施例２２と同様にして
ドラム状の比較用感光体を作成し、実施例２２と同様に
して複写画像を評価したところ、カブリが多い画像しか
得られなかった。Comparative Example 3 A drum-shaped comparative photoreceptor was prepared in the same manner as in Example 22, except that an azo compound represented by the following structural formula (G-3) was used as the carrier source substance, and the same process as in Example 22 was carried out. When the copied images were evaluated, only images with a lot of fog were obtained.
又、複写を繰返していくに従い、複写画像のコントラス
トが低下し、ｓ、ｏｏｏ回繰返１′とほとんど複写画像
は得られなかった。Furthermore, as the copying was repeated, the contrast of the copied image decreased, and after s, ooo times of repetition 1', hardly any copied image could be obtained.
（Ｇ−３）
実施例２３
ポリエステルフィルム上にアルミニウム箔をラミネート
して成る１ｍ性支持体上に、塩化ビニル−酢酸ビニル−
無水マレイン酸共重合体「エスレックＭＦ−１０４（ｌ
Ｉ！ｉ水化学社製）より成る厚さＯ，ＯＳμ醜の中間層
を設（プ、その上にキャリア輸送物質として下記構造式
（Ｋ−１０）のもの６ｇとポリカーボネート樹脂「パン
ライトＬ −１２５０Ｊ１０（＋とを１．２−ジクロロ
エタン８０１ｇに溶解した液を乾燥後の膜厚が１５μ腸
になるように塗布して、キャリア輸送層を形成した。(G-3) Example 23 Vinyl chloride-vinyl acetate-
Maleic anhydride copolymer “S-LEC MF-104 (l
I! An intermediate layer with a thickness of O and OS μ was formed (manufactured by Mizu Kagaku Co., Ltd.) on which 6 g of a carrier transport material having the structural formula (K-10) and polycarbonate resin Panlite L-1250J10 ( A carrier transport layer was formed by applying a solution prepared by dissolving 1.2-dichloroethane and 1.2-dichloroethane in 801 g of 1.2-dichloroethane so that the film thickness after drying was 15 μm.
（Ｋ−１０＞
更にその上に例示化合物ＮＯ，３２，２０、上記キャリ
ア輸送物ｖ１１．５１Ｊ 、ポリカーボネート樹脂［パ
ンライト１．−１２５０．１２０とを１．２−ジクロロ
エタン７０ｄと１．１．２−１−ジクロロエタン３０−
に加え、２４時間ボールミルで分散した液を塗布し、乾
燥後の膜厚が４μ−であるキャリア発生層を設け、感光
体を作成した。(K-10> Furthermore, exemplified compound NO, 32, 20, the above carrier transport material v11.51J, polycarbonate resin [Panlite 1.-1250.120 and 1.2-dichloroethane 70d and 1.1.2 -1-dichloroethane 30-
In addition, a carrier generation layer having a thickness of 4 μm after drying was provided by applying a dispersion liquid using a ball mill for 24 hours to prepare a photoreceptor.
この感光体について実施例１と同様にして測定したとこ
ろ第６表に示す結果を得た。When this photoreceptor was measured in the same manner as in Example 1, the results shown in Table 6 were obtained.
第６表
実施例２４
アルミニウムを蒸着した厚さ １００μｍのポリエチレ
ンテレフタレートより成る導電性支持体上に、ｐ−ヒド
ロキシスチレンの重合体「マルゼンレジンＭｌ （丸
善石油社製）より成る厚さ約０．２μｍの下引層を形成
した。Table 6 Example 24 Aluminum was deposited on a conductive support made of polyethylene terephthalate with a thickness of 100 μm and made of a p-hydroxystyrene polymer “Maruzen Resin Ml (manufactured by Maruzen Sekiyu Co., Ltd.) with a thickness of about 0.2 μm. A subbing layer was formed.
つぎに、ポリカーボネート樹脂「パンライトＬ−１２５
０Ｊ （余人化成社製）ｏ、ｓｇ、例示化合物ＮＯ，
８２，ｌ及び、１．２−ジクロロエタン１００顧をサン
ドミルで１０時間混合分散して１ｑられ分散液を、ワイ
ヤーバー塗布法により、前記下引層上に塗布し、１００
℃で１０分間乾燥して膜厚的０゜２μｍのキャリア発生
層を形成した。Next, polycarbonate resin “Panlite L-125
0J (manufactured by Yojin Kasei Co., Ltd.) o, sg, exemplified compound NO,
82,1 and 100 g of 1,2-dichloroethane were mixed and dispersed in a sand mill for 10 hours, and the resulting dispersion was coated on the undercoat layer using a wire bar coating method.
It was dried at .degree. C. for 10 minutes to form a carrier generation layer having a thickness of 0.2 .mu.m.
さらに、キャリア輸送物質として（Ｋ−３）１２（＋と
アクリル樹脂「ダイアナールＢＲ−８０Ｊ（三菱レーヨ
ン社製）１５ｇとを１，２−ジクロロエタン１００ｉに
溶解した溶液を前記キャリア発生層上にドクターブレー
ドを用いて塗布し、温度９０℃で１時間乾燥して膜厚的
２０μｍのキャリア輸送層を形成し、以って本発明の感
光体を製造した。Furthermore, a solution prepared by dissolving (K-3) 12 (+ as a carrier transport substance) and 15 g of an acrylic resin "Dianaru BR-80J (manufactured by Mitsubishi Rayon Co., Ltd.) in 100 i of 1,2-dichloroethane was applied to the carrier generation layer using a doctor blade. A carrier transport layer having a thickness of 20 .mu.m was formed by coating the photoreceptor using the following method and drying at a temperature of 90.degree. C. for 1 hour to produce a photoreceptor of the present invention.
本発明の感光体について、波長７８０±１１のレーザー
光源（出力１＋ａＷ）を搭載したｒ Ｕ −Ｂ ｉＸ１
５５０Ｍ ＲＪ （コニカ株式会社製）改造機を用い
、帯電電位が一〇００Ｖになるようにグリッド電圧を調
節し、評価した。感光体にお１ノる実機内電位の評価結
果を下記第７表に示す。Regarding the photoreceptor of the present invention, r U -B iX1 equipped with a laser light source with a wavelength of 780±11 (output 1+aW)
Using a modified 550M RJ (manufactured by Konica Corporation), the grid voltage was adjusted so that the charging potential was 1,000 V, and evaluation was performed. The evaluation results of the actual internal potential of the photoreceptor are shown in Table 7 below.
第７表
■１．Ｉ：未露光部の表面電位
■Ｌ ：露光部の表面電位
以上の結果から明らかなように本発明の感光体は半導体
レーザー光源に対しても十分な感度を有していることが
わかった。Table 7■1. I: Surface potential of unexposed area ■L: Surface potential of exposed area As is clear from the results above, it was found that the photoreceptor of the present invention has sufficient sensitivity even to a semiconductor laser light source.
以上の実施例、比較例の結果から明らかなように本発明
の感光体は比較用感光体に比べ、安定性、感度、耐久性
、広範なキャリア輸送物質との組合せ等の特性において
著しく優れたものである。As is clear from the results of the above Examples and Comparative Examples, the photoreceptor of the present invention is significantly superior to the comparative photoreceptor in properties such as stability, sensitivity, durability, and compatibility with a wide range of carrier transport substances. It is something.
第１図〜第６図はそれぞれ本発明の感光体の構成例につ
いて示す断面図である。
１・・・導電性支持体 ２・・・キャリア発生層３・
・・キャリア輸送Ｍ ４・・・感光Ｊ１５・・・中門層
６・・・キャリア輸送物質を含有する層７・・・キャリ
ア発生物質FIGS. 1 to 6 are cross-sectional views showing structural examples of the photoreceptor of the present invention, respectively. 1... Conductive support 2... Carrier generation layer 3.
...Carrier transport M4...Photosensitive J15...Middle layer 6...Layer containing carrier transport substance 7...Carrier generating substance
Claims (3)
ビスアゾ化合物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［ I ］ ▲数式、化学式、表等があります▼ ［式中、Ｃｐはカプラー残基を表わす。Ｘ＿１は水素原
子、シアノ基又はハロゲン原子を表わし、Ｘ＿２は▲数
式、化学式、表等があります▼、−Ｏ−又は−Ｓ−を表
わす。］(1) An electrophotographic photoreceptor comprising a photosensitive layer containing a bisazo compound represented by the following general formula [I] on a conductive support. General formula [I] ▲Mathematical formulas, chemical formulas, tables, etc.▼ [In the formula, Cp represents a coupler residue. X_1 represents a hydrogen atom, a cyano group, or a halogen atom, and X_2 represents ▲numerical formula, chemical formula, table, etc.▼, -O- or -S-. ]
質とを含有し、該キャリア発生物質が前記一般式［ I
］で表わされるビスアゾ化合物であることを特徴とする
請求項１記載の電子写真感光体。(2) The photosensitive layer contains a carrier transporting substance and a carrier generating substance, and the carrier generating substance has the general formula [I
2. The electrophotographic photoreceptor according to claim 1, which is a bisazo compound represented by the following formula.
ア発生層と、キヤリア輸送物質を含有するキャリア輸送
層との積層体で構成されていることを特徴とする請求項
１記載の電子写真感光体。(3) The electrophotographic photoreceptor according to claim 1, wherein the photosensitive layer is composed of a laminate of a carrier generation layer containing a carrier generation substance and a carrier transport layer containing a carrier transport substance. .
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP204188A JPH01179160A (en) | 1988-01-08 | 1988-01-08 | Electrophotographic sensitive body |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP204188A JPH01179160A (en) | 1988-01-08 | 1988-01-08 | Electrophotographic sensitive body |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH01179160A true JPH01179160A (en) | 1989-07-17 |
Family
ID=11518240
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP204188A Pending JPH01179160A (en) | 1988-01-08 | 1988-01-08 | Electrophotographic sensitive body |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01179160A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0591010A1 (en) * | 1992-10-02 | 1994-04-06 | Mita Industrial Co., Ltd. | Organic photosensitive material for electrophotography |
-
1988
- 1988-01-08 JP JP204188A patent/JPH01179160A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0591010A1 (en) * | 1992-10-02 | 1994-04-06 | Mita Industrial Co., Ltd. | Organic photosensitive material for electrophotography |
| US5449580A (en) * | 1992-10-02 | 1995-09-12 | Mita Industrial Co., Ltd. | Organic photosensitive material for electrophotography |
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| JPH01179161A (en) | Electrophotographic sensitive body | |
| JPH01179159A (en) | Electrophotographic sensitive body | |
| JPH01147549A (en) | Electrophotographic sensitive body | |
| JPH01179162A (en) | Electrophotographic sensitive body | |
| JPH01179156A (en) | Electrophotographic sensitive body | |
| JPH01179155A (en) | Electrophotographic sensitive body | |
| JP3125243B2 (en) | Electrophotographic photoreceptor | |
| JPH0220877A (en) | Electrophotographic sensitive body | |
| JPH01198761A (en) | Electrophotographic sensitive body | |
| JPH01147550A (en) | Electrophotographic sensitive body | |
| JPH04146445A (en) | Electrophotographic sensitive body | |
| JPH0337657A (en) | Photosensitive body | |
| JPH03120553A (en) | Electrophotographic sensitive body | |
| JPH01147548A (en) | Electrophotographic sensitive body | |
| JPH04146444A (en) | Electrophotographic sensitive body | |
| JPH04139454A (en) | Electrophotographic sensitive body | |
| JPH04162045A (en) | Electrophotographic photosensitive body | |
| JPH01284859A (en) | Electrophotographic sensitive body | |
| JPH04191859A (en) | Electrophotographic sensitive body | |
| JPH04161960A (en) | Sensitive substance for electrophotograph | |
| JPH05158263A (en) | Electrophotographic sensitive body |