JPS63180960A - Electrophotographic sensitive body - Google Patents
Electrophotographic sensitive bodyInfo
- Publication number
- JPS63180960A JPS63180960A JP1133487A JP1133487A JPS63180960A JP S63180960 A JPS63180960 A JP S63180960A JP 1133487 A JP1133487 A JP 1133487A JP 1133487 A JP1133487 A JP 1133487A JP S63180960 A JPS63180960 A JP S63180960A
- Authority
- JP
- Japan
- Prior art keywords
- group
- formulas
- tables
- formula
- layer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000000049 pigment Substances 0.000 claims abstract description 33
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims abstract description 19
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 8
- 125000001424 substituent group Chemical group 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
- 125000003367 polycyclic group Chemical group 0.000 claims abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 3
- 108091008695 photoreceptors Proteins 0.000 claims description 30
- 239000000126 substance Substances 0.000 claims description 19
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000000758 substrate Substances 0.000 abstract description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract description 9
- 230000035945 sensitivity Effects 0.000 abstract description 6
- 238000009833 condensation Methods 0.000 abstract description 2
- 230000005494 condensation Effects 0.000 abstract description 2
- 239000010408 film Substances 0.000 description 16
- -1 for example Polymers 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 238000000576 coating method Methods 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 238000001035 drying Methods 0.000 description 11
- 239000000463 material Substances 0.000 description 10
- 239000011347 resin Substances 0.000 description 10
- 229920005989 resin Polymers 0.000 description 10
- 239000011248 coating agent Substances 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 239000011230 binding agent Substances 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- 239000005018 casein Substances 0.000 description 6
- 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 6
- 235000021240 caseins Nutrition 0.000 description 6
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 6
- 239000002800 charge carrier Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000004372 Polyvinyl alcohol Substances 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
- 210000003127 knee Anatomy 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 229920002451 polyvinyl alcohol Polymers 0.000 description 4
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-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
- 229920000178 Acrylic resin Polymers 0.000 description 3
- 239000004925 Acrylic resin Substances 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 229920002382 photo conductive polymer Polymers 0.000 description 3
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 3
- 229920001230 polyarylate Polymers 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- VDFKURANQKCOAI-UHFFFAOYSA-N 1-nitrofluoren-9-one Chemical compound C12=CC=CC=C2C(=O)C2=C1C=CC=C2[N+](=O)[O-] VDFKURANQKCOAI-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
- 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 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000004677 Nylon Substances 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 229910052980 cadmium sulfide Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- 238000003618 dip coating Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000007857 hydrazones Chemical class 0.000 description 2
- 230000031700 light absorption Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229920001778 nylon Polymers 0.000 description 2
- 230000003287 optical effect Effects 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
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920002401 polyacrylamide Polymers 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 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
- 229910052711 selenium Inorganic materials 0.000 description 2
- 239000011669 selenium Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical group ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- FKNIDKXOANSRCS-UHFFFAOYSA-N 2,3,4-trinitrofluoren-1-one Chemical compound C1=CC=C2C3=C([N+](=O)[O-])C([N+]([O-])=O)=C([N+]([O-])=O)C(=O)C3=CC2=C1 FKNIDKXOANSRCS-UHFFFAOYSA-N 0.000 description 1
- BNEIZVAKXQXPAZ-UHFFFAOYSA-N 2-(1-oxo-2h-fluoren-9-ylidene)propanedinitrile Chemical compound N#CC(C#N)=C1C2=CC=CC=C2C2=C1C(=O)CC=C2 BNEIZVAKXQXPAZ-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- WGRSVHBSCVGKDP-UHFFFAOYSA-N 2-ethyl-9h-carbazole-1-carbaldehyde Chemical compound C1=CC=C2C3=CC=C(CC)C(C=O)=C3NC2=C1 WGRSVHBSCVGKDP-UHFFFAOYSA-N 0.000 description 1
- YGBCLRRWZQSURU-UHFFFAOYSA-N 4-[(diphenylhydrazinylidene)methyl]-n,n-diethylaniline Chemical compound C1=CC(N(CC)CC)=CC=C1C=NN(C=1C=CC=CC=1)C1=CC=CC=C1 YGBCLRRWZQSURU-UHFFFAOYSA-N 0.000 description 1
- PGDARWFJWJKPLY-UHFFFAOYSA-N 4-[2-[3-[4-(diethylamino)phenyl]-2-phenyl-1,3-dihydropyrazol-5-yl]ethenyl]-n,n-diethylaniline Chemical compound C1=CC(N(CC)CC)=CC=C1C=CC1=CC(C=2C=CC(=CC=2)N(CC)CC)N(C=2C=CC=CC=2)N1 PGDARWFJWJKPLY-UHFFFAOYSA-N 0.000 description 1
- UZGVMZRBRRYLIP-UHFFFAOYSA-N 4-[5-[4-(diethylamino)phenyl]-1,3,4-oxadiazol-2-yl]-n,n-diethylaniline Chemical compound C1=CC(N(CC)CC)=CC=C1C1=NN=C(C=2C=CC(=CC=2)N(CC)CC)O1 UZGVMZRBRRYLIP-UHFFFAOYSA-N 0.000 description 1
- XXWVEJFXXLLAIB-UHFFFAOYSA-N 4-[[4-(diethylamino)-2-methylphenyl]-phenylmethyl]-n,n-diethyl-3-methylaniline Chemical compound CC1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)N(CC)CC)C)C1=CC=CC=C1 XXWVEJFXXLLAIB-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
- LSZJZNNASZFXKN-UHFFFAOYSA-N 9-propan-2-ylcarbazole Chemical compound C1=CC=C2N(C(C)C)C3=CC=CC=C3C2=C1 LSZJZNNASZFXKN-UHFFFAOYSA-N 0.000 description 1
- 229910000838 Al alloy Inorganic materials 0.000 description 1
- 235000018185 Betula X alpestris Nutrition 0.000 description 1
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
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- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 235000000177 Indigofera tinctoria Nutrition 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
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- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
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- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
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- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- SUJMFQYAKKPLSH-UHFFFAOYSA-N n-[[4-(diethylamino)phenyl]methylideneamino]-n-phenylnaphthalen-1-amine Chemical compound C1=CC(N(CC)CC)=CC=C1C=NN(C=1C2=CC=CC=C2C=CC=1)C1=CC=CC=C1 SUJMFQYAKKPLSH-UHFFFAOYSA-N 0.000 description 1
- XRWSIBVXSYPWLH-UHFFFAOYSA-N n-phenyl-n-[(4-pyrrolidin-1-ylphenyl)methylideneamino]aniline Chemical compound C1CCCN1C(C=C1)=CC=C1C=NN(C=1C=CC=CC=1)C1=CC=CC=C1 XRWSIBVXSYPWLH-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 239000003960 organic solvent Substances 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
- 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
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene 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
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 229920002717 polyvinylpyridine Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- SCUZVMOVTVSBLE-UHFFFAOYSA-N prop-2-enenitrile;styrene Chemical compound C=CC#N.C=CC1=CC=CC=C1 SCUZVMOVTVSBLE-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003219 pyrazolines Chemical class 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
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- PWEBUXCTKOWPCW-UHFFFAOYSA-N squaric acid Chemical compound OC1=C(O)C(=O)C1=O PWEBUXCTKOWPCW-UHFFFAOYSA-N 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229910052714 tellurium Inorganic materials 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
- 150000003557 thiazoles Chemical class 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-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
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/06—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
- G03G5/0681—Disazo dyes containing hetero rings in the part of the molecule between the azo-groups
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (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、詳しくは特定の構造のジスア
ゾ顔料よりなる有機光導電性物質を含有する感光層を有
する電子写真感光体に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to an electrophotographic photoreceptor, and more particularly to an electrophotographic photoreceptor having a photosensitive layer containing an organic photoconductive substance consisting of a disazo pigment having a specific structure.
[従来の技術]
これまで、セレン、硫化カドミウム、酸化亜鉛などの無
機光導電体を感光層に含有する電子写真感光体はよく知
られている。一方、例えばポリ−N−ビニルカルバゾー
ル、ポリビニルアントラセンなどの有機光導電性ポリマ
ー、カルバゾール。[Prior Art] Electrophotographic photoreceptors containing inorganic photoconductors such as selenium, cadmium sulfide, and zinc oxide in the photosensitive layer are well known. On the other hand, organic photoconductive polymers, carbazoles, such as, for example, poly-N-vinylcarbazole, polyvinylanthracene.
アントラセン、ピラゾリン類、オキサジアゾール類、ヒ
ドラゾン類などの低分子の有機光導電体やフタロシアニ
ン顔料、アゾ顔料、インジゴ染料。Low-molecular organic photoconductors such as anthracene, pyrazolines, oxadiazoles, and hydrazones, phthalocyanine pigments, azo pigments, and indigo dyes.
チオインジゴ染料、スクエアリック酸メチン染料などの
有機光導電体が開発されてきた。さらに。Organic photoconductors such as thioindigo dyes and methine squaric acid dyes have been developed. moreover.
例えば米国特許第4123270号明細書、米国特許第
4247614号明細書、米国特許第4251613号
明細書、米国特許第4258821号明細書などに開示
されているとおり、電荷発生層と電荷輸送層に機能分離
した感光層における電荷発生物質として光導電性のジス
アゾ顔料を用いた電子写真感光体が知られている。For example, as disclosed in U.S. Pat. No. 4,123,270, U.S. Pat. No. 4,247,614, U.S. Pat. No. 4,251,613, and U.S. Pat. No. 4,258,821, functional separation into a charge generation layer and a charge transport layer An electrophotographic photoreceptor using a photoconductive disazo pigment as a charge generating substance in a photosensitive layer is known.
このような有機光導電体を用いた電子写真感光体はバイ
ンダーを適当に選択することにより浸漬コーティングに
よる塗工法を用いて生産できるため極めて生産性が高く
安価な感光体を提供でき。An electrophotographic photoreceptor using such an organic photoconductor can be produced using a coating method by dip coating by appropriately selecting a binder, so that a photoreceptor with extremely high productivity and low cost can be provided.
しかも適当な波長域に光導電性を呈する有機顔料を選択
できるという利点がある反面、感度と繰返し使用に対す
る耐久性に難点があるため、これまで実用化されている
ものはごく僅かである。Moreover, although it has the advantage of being able to select an organic pigment that exhibits photoconductivity in an appropriate wavelength range, it has drawbacks in sensitivity and durability against repeated use, and so far only a few have been put into practical use.
[発明が解決しようとする問題点]
本発明の目的は新規な有機光導電体を感光層に含有する
電子写真感光体を提供することにある。[Problems to be Solved by the Invention] An object of the present invention is to provide an electrophotographic photoreceptor containing a novel organic photoconductor in its photosensitive layer.
さらに別の目的は実用的な高感度を有し、かつ繰返し使
用後も安定な帯電特性を示す電子写真感光体を提供する
ことにある。Still another object is to provide an electrophotographic photoreceptor that has high sensitivity for practical use and exhibits stable charging characteristics even after repeated use.
[問題点を解決する手段、作用]
本発明は、導電性基体上に設けられた感光層に下記一般
式(1)で示されるジスアゾ顔料の少なくとも一種を光
導電体として含有することを特徴とする電子写真感光体
から構成される。[Means and effects for solving the problems] The present invention is characterized in that a photosensitive layer provided on a conductive substrate contains at least one type of disazo pigment represented by the following general formula (1) as a photoconductor. It consists of an electrophotographic photoreceptor.
一般式(1)
式中、Aはフェノール性OH基を有するカップラー残基
または2−メチルインドレニン誘導体のカップラー残基
を示す。General Formula (1) In the formula, A represents a coupler residue having a phenolic OH group or a coupler residue of a 2-methylindolenine derivative.
さらに詳しくは、上記一般式(1)におけるカップラー
残基Aは、例えば下記一般式(2)〜(8)のいずれか
で示される基である。More specifically, the coupler residue A in the above general formula (1) is, for example, a group represented by any of the following general formulas (2) to (8).
一般式
NO
式中、R1およびR2は水素原子、置換基を有してもよ
いアルキル基、アラルキル基、アリール基、ヘテロ環基
、イミノ基あるいはR1、R2の結合する窒素原子と一
緒に環状アミノ基を示し、又はベンゼン環と縮合して多
環芳香環あるいはへテロ環を形成する残基を示し、R3
およびR4は置換基を宥してもよいアルキル基、アラル
キル基あるいはアリール基を示し、Yは芳香族炭化水素
の2価の基あるいは窒素原子と共にペテロ環を形成する
2価の基を示し、R5およびR6は水素原子、アルキル
基、アルコキシ基、ノ\ロゲン原子、シアノ基あるいは
ニトロ基を示す。General formula NO In the formula, R1 and R2 are a hydrogen atom, an alkyl group that may have a substituent, an aralkyl group, an aryl group, a heterocyclic group, an imino group, or a cyclic amino group together with the nitrogen atom to which R1 and R2 are bonded. represents a group, or represents a residue that forms a polycyclic aromatic ring or a heterocycle by condensing with a benzene ring, and R3
and R4 represents an alkyl group, an aralkyl group, or an aryl group which may have a substituent, Y represents a divalent group of aromatic hydrocarbon or a divalent group forming a petro ring together with a nitrogen atom, and R5 and R6 represents a hydrogen atom, an alkyl group, an alkoxy group, a norogen atom, a cyano group or a nitro group.
上記定義において、アルキル基、アラルキル基、アリー
ル基、アルコキシ基およびヘテロ環基の例としては、ア
ルキル基は例えばメチル、エチル、プロピルなど、アラ
ルキル基は例えばベンジル、ナフチルメチルなど、アリ
ール基は例えばフェニル、ジフェニル、ナフチル、アン
スリルなど、アルコキシ基は例えばメトキシ、エトキシ
、プロポキシなど、ヘテロ環基は例えばジベンゾフラン
、ベンズイミダシロン、ベンズチアゾール、チアゾール
、ピリジンなどが挙げられる。In the above definitions, examples of alkyl groups, aralkyl groups, aryl groups, alkoxy groups and heterocyclic groups include alkyl groups such as methyl, ethyl and propyl; aralkyl groups such as benzyl and naphthylmethyl; and aryl groups such as phenyl. , diphenyl, naphthyl, anthryl, etc.; examples of alkoxy groups include methoxy, ethoxy, propoxy, etc.; examples of heterocyclic groups include dibenzofuran, benzimidacylon, benzthiazole, thiazole, pyridine, etc.
上記アルキル基、アラルキル基、アリール基、アルコキ
シ基、ヘテロ環基およびイミノ基における置換基として
は例えばハロゲン原子、ニトロ基、シアノ基、置換アミ
ノ基(例えばジメチルアミノ、ジフェニルアミノ、ジベ
ンジルアミノなど)、アルキル基、アルコキシ基などが
挙げられる。Substituents for the above alkyl groups, aralkyl groups, aryl groups, alkoxy groups, heterocyclic groups and imino groups include, for example, halogen atoms, nitro groups, cyano groups, substituted amino groups (e.g. dimethylamino, diphenylamino, dibenzylamino, etc.) , an alkyl group, an alkoxy group, and the like.
またXのベンゼン環と共に多環芳香族環あるいはへテロ
環を形成する残基としては例えばナフタレン環、アント
ラセン環、カルバゾール環、ベンズカルバゾール環、ジ
ベンゾフラン環、ベンゾナフトフラン環、ジフェニレン
サルファイド環などが挙げられる。Examples of residues that form a polycyclic aromatic ring or heterocycle with the benzene ring of Can be mentioned.
またYの2価の基としては例えばフェニレン基ナフチレ
ン基などが挙げられる。Further, examples of the divalent group of Y include phenylene group and naphthylene group.
以下、前記一般式(1)で示されるジスアゾ顔料の代表
例を列挙する。Representative examples of the disazo pigment represented by the general formula (1) are listed below.
なお、下記基本型においてAのみが相違するので例示は
Aのみを示すこととする。Note that in the following basic types, only A is different, so only A is shown as an example.
節
これらのジスアゾ顔料は、1種または2種以上を組合せ
て用いることができる。These disazo pigments can be used alone or in combination of two or more.
これらのジスアゾ顔料は、
例えば
門
で示されるジアミンを常法によりテトラゾ化して、これ
に、対応する前記一般式(2)〜(8)で示される基を
有するカップラーをアルカリの存在下にカップリングす
るか、または上記のジアミンのテトラゾニウム塩をホウ
フッ化塩あるいは塩化亜鉛複塩などの形で一旦単離した
後、適当な溶媒例えば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アルカリの存在下
に対応する前記一般式(2)〜(8)で示される基を有
するカップラーとカップリングすることにより容易に製
造することができる。These disazo pigments can be obtained by, for example, tetrazotizing the diamine represented by the following formula using a conventional method, and coupling the resultant with a coupler having a group represented by the corresponding general formulas (2) to (8) above in the presence of an alkali. Alternatively, once the tetrazonium salt of the diamine described above is isolated in the form of a borofluoride salt or a zinc chloride double salt, a suitable solvent such as N,N-dimethylformamide,
It can be easily produced by coupling with a coupler having a group represented by the corresponding general formulas (2) to (8) above in the presence of an alkali in a solvent such as dimethyl sulfoxide.
例示顔料(1)の合成例
500 m文ビーカーに水80m立、濃塩酸16.6
m文(0,19モル)および前記ジアミン12・5g
(0,029モル)を入れ、氷水浴で冷却しながら攪拌
して液温を3℃とした。Synthesis example of exemplified pigment (1) 500 m beaker, 80 ml of water, 16.6 m of concentrated hydrochloric acid
m (0.19 mol) and 12.5 g of said diamine
(0,029 mol) was added and stirred while cooling in an ice water bath to bring the liquid temperature to 3°C.
次に亜硝酸ソーダ4.2g(0,061モル)を水71
11文に溶した液を、液温を3〜10″Cの範囲にコン
トロールしながら1o分間で滴下し、滴下終了後同温度
で更に30分間攪拌した0反応液にカーボンを加え癌過
してテトラゾ化液を得た。Next, add 4.2 g (0,061 mol) of sodium nitrite to 71 ml of water.
Add the solution dissolved in No. 11 over a period of 10 minutes while controlling the temperature within the range of 3 to 10"C. After the dropwise addition, stir at the same temperature for another 30 minutes. Add carbon to the reaction solution and sieve. A tetrazotized solution was obtained.
次に2文ビーカーに水700m1を入れ、苛性ソーダ2
1g(0,53モル)を溶解した後、ナフトールAS
(3−ヒドロキシ−2−ナフトエ酸アニリド)16.2
g (0,061モル) を添加して溶解した。このカ
ップラー溶液を6℃に冷却し、液温を6〜10℃にコン
トロー)ししながら上記のテトラゾ化液を30分かけて
攪拌下滴下してその後室温で2時間攪拌し、更に1晩放
置した。Next, pour 700ml of water into a beaker and add 2ml of caustic soda.
After dissolving 1 g (0.53 mol) of naphthol AS
(3-hydroxy-2-naphthoic acid anilide) 16.2
g (0,061 mol) was added and dissolved. This coupler solution was cooled to 6°C, and the above tetrazotized solution was added dropwise with stirring over 30 minutes while controlling the liquid temperature at 6 to 10°C.Then, the coupler solution was stirred at room temperature for 2 hours, and then left overnight. did.
反応液を濾過後水洗し、粗製顔料24.0gを得た。The reaction solution was filtered and washed with water to obtain 24.0 g of a crude pigment.
次に400mJljのN、N−ジメチルホルムアミドで
熱濾過を5回繰り返した。その後、減圧熱乾燥により精
製顔料22.7gを得た。Hot filtration was then repeated five times with 400 mJlj of N,N-dimethylformamide. Thereafter, 22.7 g of purified pigment was obtained by heat drying under reduced pressure.
収率は79.9%であった。The yield was 79.9%.
元素分析:
計算値(%) 実験値(%)
C73,5473,51
H3,813,78
N 12.86 12.83
前記一般式(1)で示されるジスアゾ顔料を含有する被
膜は、光導電性を示し、従って電子写真感光体の感光層
に用いることができる。Elemental analysis: Calculated value (%) Experimental value (%) C73,5473,51 H3,813,78 N 12.86 12.83 The film containing the disazo pigment represented by the general formula (1) has photoconductive properties. Therefore, it can be used in the photosensitive layer of an electrophotographic photoreceptor.
電子写真感光体は、導電性基体上に前記ジスアゾ顔料を
真空蒸着法により被膜形成するか、あるいは適当なバイ
ンダーに分散含有させて被膜形成することによって作成
される。The electrophotographic photoreceptor is prepared by forming a film of the disazo pigment on a conductive substrate by vacuum evaporation, or by dispersing the disazo pigment in a suitable binder to form a film.
本発明の好ましい実施態様では感光層を電荷発生層と電
荷輸送層に機能分離した電子写真感光体における電荷発
生層として上記の光導電性被膜を使用することができる
。In a preferred embodiment of the present invention, the photoconductive coating described above can be used as a charge generation layer in an electrophotographic photoreceptor in which the photosensitive layer is functionally separated into a charge generation layer and a charge transport layer.
電荷発生層は十分な吸光分を得るためできる限り多くの
量の光導電物質を含有し、かつ発生した電荷キャリアの
飛程を短くするため被膜、例えば5μm以下、好ましく
は0.01〜lpmの膜厚の薄膜とすることが望ましい
。The charge generation layer contains as much photoconductive material as possible in order to obtain sufficient light absorption, and in order to shorten the range of the generated charge carriers, it contains a coating, for example, 5 μm or less, preferably 0.01 to lpm. It is desirable to have a thin film.
このことは入射光線の大部分が電荷発生層で吸収されて
多く電荷キャリアを生成すること、さらに発生したキャ
リアを再結合や捕獲(トラップ)により失活することな
く電荷輸送層に注入する必要があることに起因している
。This means that most of the incident light is absorbed by the charge generation layer and generates a large number of charge carriers, and that the generated carriers must be injected into the charge transport layer without being deactivated by recombination or trapping. It is caused by something.
電荷発生層は、例えば前記ジスアゾ顔料を適当なバイン
ダーに分散させこれを基体の上に塗工することによって
形成でき、また真空蒸着装置により蒸着膜を形成するこ
とによって得ることができる。電荷発生層を塗工によっ
て形成する際に用い得るバインダーとしては広範な絶縁
性樹脂から選択でき、またポリ−N−ビニルカルバゾー
ル、ポリビニルアントラセンやポリビニルピレンなどの
有機光導電性ポリマーから選択できる。好ましくはポリ
ビニルブチラール、ボリアリレート(ビスフェノールA
とフタル酸の縮重合体など)、ポリカーボネート、ポリ
エステル、フェノキシ樹脂、ポリ酢酸ビニル、アクリル
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、セルロース系樹脂、ポリウレタン、エポキシ樹
脂、カゼイン、ポリビニルアルコール、ポリビニルピロ
リドンなどの絶縁性樹脂を挙げることができる。The charge generation layer can be formed, for example, by dispersing the disazo pigment in a suitable binder and coating it on a substrate, or by forming a vapor deposited film using a vacuum vapor deposition apparatus. The binder that can be used to form the charge generating layer by coating can be selected from a wide variety of insulating resins, and can also be selected from organic photoconductive polymers such as poly-N-vinylcarbazole, polyvinylanthracene, and polyvinylpyrene. Preferably polyvinyl butyral, polyarylate (bisphenol A
and phthalic acid condensation polymers, etc.), polycarbonate, polyester, phenoxy resin, polyvinyl acetate, acrylic resin, polyacrylamide, polyamide, polyvinylpyridine, cellulose resin, polyurethane, epoxy resin, casein, polyvinyl alcohol, polyvinylpyrrolidone, etc. Examples include insulating resins.
電荷発生層中に含有する樹脂は、80重量%以下、好ま
しくは40重量%以下が適している。The resin contained in the charge generation layer is suitably 80% by weight or less, preferably 40% by weight or less.
これらの樹脂を溶解する溶剤は、樹脂の種類によって異
なり、また後述の電荷輸送層や下引層を溶解しないもの
から選択することが好ましい。The solvent that dissolves these resins varies depending on the type of resin, and is preferably selected from those that do not dissolve the charge transport layer and undercoat layer described below.
具体的な有機溶剤としては、メタノール、エタノール、
イソプロパツールなどのアルコール類、アセトン、メチ
ルエチルケトン、シクロヘキサノンなどのケトン類、N
、N−ジメチルホルムアミド、N、N−ジメチルアセト
アミドなどのアミド類、ジメチルスルホキシドなどのス
ルホキシド類、テトラヒドロフラン、ジオキサン、エチ
レングリコールモノメチルエーテルなどのエーテル類。Specific organic solvents include methanol, ethanol,
Alcohols such as isopropanol, ketones such as acetone, methyl ethyl ketone, cyclohexanone, N
, amides such as N-dimethylformamide and N,N-dimethylacetamide, sulfoxides such as dimethyl sulfoxide, and ethers such as tetrahydrofuran, dioxane, and ethylene glycol monomethyl ether.
酢酸メチル、酢酸エチルなどのエステル類、クロロホル
ム、塩化メチレン、ジクロルエチレン、四塩化炭素、ト
リクロルエチレンなどの脂肪族ハロゲン化炭化水素類あ
るいはベンゼン、トルエン。Esters such as methyl acetate and ethyl acetate, aliphatic halogenated hydrocarbons such as chloroform, methylene chloride, dichloroethylene, carbon tetrachloride, and trichloroethylene, or benzene and toluene.
キシレン、リグロイン、モノクロルベンゼン、ジクロル
ベンゼンなどの芳香族炭化水素類などを用いることがで
きる。Aromatic hydrocarbons such as xylene, ligroin, monochlorobenzene, dichlorobenzene, etc. can be used.
塗工は、浸漬コーティング法、スプレーコーティング法
、スピンナーコーティング法などのコーティング法を用
いて行なうことができる。Coating can be performed using a coating method such as a dip coating method, a spray coating method, or a spinner coating method.
乾燥は、室温における指触乾燥後、加熱乾燥する方法が
好ましい、加熱乾燥は、30〜200℃の温度で5分〜
2時間の範囲の時間で、静止または送風下で行なうこと
ができる。Drying is preferably carried out by drying to the touch at room temperature and then heating. Drying by heating is performed at a temperature of 30 to 200°C for 5 minutes to
It can be carried out stationary or under blown air for a time in the range of 2 hours.
電荷輸送層は、前述の電荷発生層と電気的に接続されて
おり、電界の存在下で電荷発生層から注入された電荷キ
ャリアを受は取るとともに、これらの電荷キャリアを表
面まで輸送できる機能を有している。この際、この電荷
輸送層は電荷発生層の上にa層されていてもよく、また
その下に積層されていてもよい。The charge transport layer is electrically connected to the charge generation layer described above, and has the function of receiving and taking charge carriers injected from the charge generation layer in the presence of an electric field, and transporting these charge carriers to the surface. have. At this time, this charge transport layer may be formed as an a-layer on top of the charge generation layer, or may be laminated below it.
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
があり、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−)りニトロ−9−フルオレノン、2
,4,5.7−テトラニトロ−9−フルオレノン、2,
4.7−ドリニトロー9−ジシアノメチレンフルオレノ
ン、2.4,5.7−チトラニトロキサントン、2,4
.8−トリニドロチオキサントンなどの電子吸引性物質
やこれら電子吸引性物質を高分子化したものなどがある
。Charge-transporting substances include electron-transporting substances and hole-transporting substances, and electron-transporting substances include chloranil, bromoanil, tetracyanoethylene, tetracyanoquinodimethane, 2,4.7-)nitro-9- Fluorenone, 2
,4,5.7-tetranitro-9-fluorenone,2,
4.7-dolinitro 9-dicyanomethylenefluorenone, 2.4,5.7-titranitroxanthone, 2,4
.. Examples include electron-withdrawing substances such as 8-trinidrothioxanthone, and polymerization of these electron-withdrawing substances.
正孔輸送性物質としてはピレン、N−エチルカルバゾー
ル、N−イソプロピルカルバゾール、N−メチル−N−
フェニルヒドラジノ−3−メチリデン−9−エチルカル
バゾール、N、N−ジフェニルヒドラジノ−3−メチリ
デン−9−エチルカルバゾール、N、N−ジフェニルヒ
ドラジノ−3−メチリデン−10−二チルフェノチアジ
ン、N、N−ジフェニルヒドラジノ−3−メチリデン−
10−エチルフェノキサジン、p−ジエチルアミノベン
ズアルデヒド−N、N−ジフェニルヒドラゾン、p−ジ
エチルアミノベンズアルデヒド−N−α−ナフチル−N
−フェニルヒドラゾン、p −ピロリジノベンズアルデ
ヒド−N、N−ジフェニルヒドラゾン、1,3.3−)
リメチルインドレニンーω−フルデヒドーN、N−ジフ
ェニルヒドラゾンなどのヒドラゾン類、2.5−ビス(
p−ジエチルアミノフェニル)−1,3,4−オキサジ
アゾール、1−フェニル−3−(p−ジエチルアミノス
チリル)−5−(p−ジエチルアミノフェニル)ピラゾ
リン、1−[ピリジル(2)] −3−(P−ジエチル
アミノスチリル)−5−(p−ジエチルアミノフェニル
)ピラゾリン、1−[ピリジル(3)]−3−(p−ジ
エチルアミノスチリル)−5−(p−ジエチルアミノフ
ェニル)ピラゾリン、1−[ピリジル(2)] −3−
(P−ジエチルアミノスチリル)−4−メチル−5−(
p−ジエチルアミノフェニル)ピラゾリン、1−フェニ
ル−3−(p−ジメチルアミノスチリJl/) −4−
メチル−5−(p−ジエチルアミノフェニル)ピラゾリ
ンなどのピラゾリン類、2−(p−ジエチルアミノスチ
リル)−6−ジニチルアミノベンズオキサゾール、2−
(P−ジエチルアミノフェニル)−4−(p−ジメチル
アミノフェニル)−5−(2−クロロフェニル)オキサ
ゾールなどのオキサゾール系化合物、2−(P−ジエチ
ルアミノスチリル)−6−ジニチルアミノベンゾチアゾ
ールなどのチアゾール系化合物、ビス(4−ジエチルア
ミノ−2−メチルフェニル)−フェニルメタンなどのト
リアリールメタン系化合物、1,1−ビス(4−N、N
−ジエチルアミノ−2−メチルフェニル)へブタン、1
,1,2.2−テトラキス(4−N、N−ジメチルアミ
ノ−2−メチルフェニル)エタンなどのボリアリールア
ルカン類、トリフェニルアミン、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−ビニルフェニルア
ントラセン、ピレンー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。Pyrene, N-ethylcarbazole, N-isopropylcarbazole, N-methyl-N-
Phenylhydrazino-3-methylidene-9-ethylcarbazole, N,N-diphenylhydrazino-3-methylidene-9-ethylcarbazole, N,N-diphenylhydrazino-3-methylidene-10-ditylphenothiazine, N, N-diphenylhydrazino-3-methylidene-
10-Ethylphenoxazine, p-diethylaminobenzaldehyde-N, N-diphenylhydrazone, p-diethylaminobenzaldehyde-N-α-naphthyl-N
-phenylhydrazone, p-pyrrolidinobenzaldehyde-N,N-diphenylhydrazone, 1,3.3-)
Limethylindolenine-ω-fuldehyde N, hydrazones such as N-diphenylhydrazone, 2,5-bis(
p-diethylaminophenyl)-1,3,4-oxadiazole, 1-phenyl-3-(p-diethylaminostyryl)-5-(p-diethylaminophenyl)pyrazoline, 1-[pyridyl(2)]-3- (P-diethylaminostyryl)-5-(p-diethylaminophenyl)pyrazoline, 1-[pyridyl(3)]-3-(p-diethylaminostyryl)-5-(p-diethylaminophenyl)pyrazoline, 1-[pyridyl( 2)] -3-
(P-diethylaminostyryl)-4-methyl-5-(
p-diethylaminophenyl) pyrazoline, 1-phenyl-3-(p-dimethylaminostiri Jl/) -4-
Pyrazolines such as methyl-5-(p-diethylaminophenyl)pyrazoline, 2-(p-diethylaminostyryl)-6-dinithylaminobenzoxazole, 2-
Oxazole compounds such as (P-diethylaminophenyl)-4-(p-dimethylaminophenyl)-5-(2-chlorophenyl)oxazole, thiazoles such as 2-(P-diethylaminostyryl)-6-dinithylaminobenzothiazole triarylmethane compounds such as bis(4-diethylamino-2-methylphenyl)-phenylmethane, 1,1-bis(4-N,N
-diethylamino-2-methylphenyl)hebutane, 1
, 1,2.2-tetrakis(4-N,N-dimethylamino-2-methylphenyl)ethane and other polyarylalkanes, triphenylamine, poly-N-vinylcarbazole, polyvinylpyrene, polyvinylanthracene, polyvinylacridine , poly-9-vinylphenylanthracene, pyrene-formaldehyde resin, and ethylcarbazole-formaldehyde resin.
これらの有機電荷輸送物質の他にセレン、セレン−テル
ル、アモルファスシリコン、硫化カドミウムなどの無機
材料も用いることができる。In addition to these organic charge transport materials, inorganic materials such as selenium, selenium-tellurium, amorphous silicon, and cadmium sulfide can also be used.
また、これらの電荷輸送物質は1種または2種以上組合
せて用いることができる。Further, these charge transport materials can be used alone or in combination of two or more.
電荷輸送物質に成膜性を宥していないときには適当なバ
インダーを選択することによって被膜形成できる。バイ
ンダーとして使用できる樹脂は、例えばアクリル樹脂、
ボリアリレート、ポリエステル、ポリカーボネート、ポ
リスチレン、アクリロニトリル−スチレンコポリマー、
アクリロニトリル−ブタジェンコポリマー、ポリビニル
ブチラール、ポリビニルホルマール、ポリスルホン、ポ
リアクリルアミド、ポリアミド、塩素化ゴムなどの絶縁
性樹脂あるいはポリ−N−ビニルカルバゾールポリビニ
ルアントラセン、ポリビニルピレンなどの素板光導電性
ポリマーが挙げられる。When the charge transport material does not have sufficient film-forming properties, a film can be formed by selecting an appropriate binder. Examples of resins that can be used as binders include acrylic resin,
polyarylate, polyester, polycarbonate, polystyrene, acrylonitrile-styrene copolymer,
Examples include insulating resins such as acrylonitrile-butadiene copolymer, polyvinyl butyral, polyvinyl formal, polysulfone, polyacrylamide, polyamide, chlorinated rubber, and base photoconductive polymers such as poly-N-vinylcarbazole polyvinylanthracene and polyvinylpyrene. .
電荷輸送層は、電荷キャリアを輸送できる限界があるの
で、必要以上に膜厚を厚くすることができない、一般的
には5〜30pmであるが、好ましい範囲は8〜207
zmである。塗工によって電荷輸送層を形成する際には
、前述したような適当なコーティング法を用いることが
できる。The charge transport layer has a limit in its ability to transport charge carriers, so it cannot be made thicker than necessary. Generally, the thickness is 5 to 30 pm, but the preferred range is 8 to 207 pm.
It is zm. When forming the charge transport layer by coating, an appropriate coating method as described above can be used.
このような電荷発生層と電荷輸送層の積層構造からなる
感光層は、導電層を有する基体の上に設けられる。導電
層を有する基体としては、基体自体が導電性をもつもの
、例えばアルミニウム、アルミニウム合金、銅、亜鉛、
ステンレス、バナジウム、モリブデン、クロム、チタン
、ニッケル。A photosensitive layer having such a laminated structure of a charge generation layer and a charge transport layer is provided on a substrate having a conductive layer. Examples of the substrate having a conductive layer include those whose substrate itself is conductive, such as aluminum, aluminum alloy, copper, zinc,
Stainless steel, vanadium, molybdenum, chromium, titanium, nickel.
インジウム、金や白金などが用いられる。Indium, gold, platinum, etc. are used.
その他にアルミニウム、アルミニウム合金、酸化インジ
ウム、酸化錫、酸化インジウム−酸化錫合金などを真空
蒸着法によって被膜形成された層を宥するプラスチック
(例えばポリエチレン、ポリプロピレン、ポリ塩化ビニ
ル、ポリエチレンテレフタレート、アクリル樹脂、ポリ
フッ化エチレンなど)、導電性粒子(例えばカーボンブ
ラック、銀粒子など)を適当なバインダーとともにプラ
スチックの上に被覆した基体、導電性粒子をプラスチッ
クや紙に含浸した基体や導電性ポリマーを有するプラス
チックなどを用いることができる。In addition, plastics (e.g., polyethylene, polypropylene, polyvinyl chloride, polyethylene terephthalate, acrylic resin, (polyfluorinated ethylene, etc.), substrates made of plastic coated with conductive particles (e.g. carbon black, silver particles, etc.) together with a suitable binder, substrates made of plastic or paper impregnated with conductive particles, plastics containing conductive polymers, etc. can be used.
導電層と感光層の中間に、バリヤー機能と接着機能をも
つ下引層を設けることもできる。下引層はカゼイン、ポ
リビニルアルコール、ニトロセルロース、エチレン−ア
クリル酸コポリマー、ポリアミド(ナイロン6、ナイロ
ン66、ナイロン610、共重合ナイロン、アルコキシ
メチル化ナイロンなど)、ポリウレタン、ゼラチン、酸
化アルミニウムなどによって形成できる。下引層の膜厚
は0.1〜5ルm、好ましくは0.5〜3ルmが適当で
ある。A subbing layer having barrier and adhesive functions can also be provided between the conductive layer and the photosensitive layer. The subbing layer can be formed from casein, polyvinyl alcohol, nitrocellulose, ethylene-acrylic acid copolymer, polyamide (nylon 6, nylon 66, nylon 610, copolymerized nylon, alkoxymethylated nylon, etc.), polyurethane, gelatin, aluminum oxide, etc. . The appropriate thickness of the undercoat layer is 0.1 to 5 m, preferably 0.5 to 3 m.
導電層、電荷発生層、電荷輸送層の順に積層した感光体
を使用する場合において電荷輸送物質が電子輸送性物質
からなるときは、電荷輸送層表面を正に帯電する必要が
あり、帯電後露光すると帯光部では電荷発生層において
生成した電子が電荷輸送層に注入され、その後表面に到
達して正電荷を中和し、表面電位の減衰が生じ未露光部
との間に静電コントラストが生じる。このようにしてで
きた静電潜像を負荷電性のトナーで現像すれば可視像が
得られる。これを直接定着するか、あるいはトナー像を
紙やプラスチックフィルムなどに転写後、現像し定着す
ることができる。また感光体上の静電潜像を転写紙の絶
縁層上に転写後視像し、定着する方法もとれる。現像剤
の種類や現像方法、定着方法は公知のものや公知の方法
のいずれを採用してもよく、特定のものに限定されるも
のではない。When using a photoreceptor in which a conductive layer, a charge generation layer, and a charge transport layer are laminated in this order, and the charge transport material is an electron transport material, the surface of the charge transport layer must be positively charged, and exposure after charging is required. Then, in the light band area, electrons generated in the charge generation layer are injected into the charge transport layer, and then reach the surface and neutralize the positive charge, causing a decrease in surface potential and creating an electrostatic contrast between it and the unexposed area. arise. A visible image is obtained by developing the electrostatic latent image thus formed with a negatively charged toner. This can be directly fixed, or the toner image can be transferred to paper or plastic film and then developed and fixed. Alternatively, a method may be used in which the electrostatic latent image on the photoreceptor is transferred onto an insulating layer of transfer paper, and then visualized and fixed. The type of developer, the developing method, and the fixing method may be any known ones or methods, and are not limited to specific ones.
一方電荷輸送物質が正孔輸送性物質からなる場合、電荷
輸送層表面を負に帯電する必要があり、帯電後、露光す
ると露光部では電荷発生層において生成した正孔が電荷
輸送層に注入され、その後表面に到達して負電荷を中和
し、表面電位の減衰が生じ未露光部との間に静電コント
ラストが生じる。現像時には電子輸送性物質を用いたと
きとは逆に正荷電性トナーを用いる必要がある。On the other hand, when the charge transport material is made of a hole transport material, the surface of the charge transport layer must be negatively charged, and when exposed to light after charging, holes generated in the charge generation layer are injected into the charge transport layer in the exposed area. , which then reaches the surface and neutralizes the negative charges, resulting in attenuation of the surface potential and an electrostatic contrast between the surface potential and the unexposed area. During development, it is necessary to use a positively charged toner, contrary to when an electron transporting substance is used.
さらに本発明の別の具体例として、前述の一般式(1)
で示されるジスアゾ顔料である有機光導電体を前述の電
荷輸送物質とともに同一層に含有させた電子写真感光体
を挙げることができる。Furthermore, as another specific example of the present invention, the above general formula (1)
Examples include an electrophotographic photoreceptor in which an organic photoconductor, which is a disazo pigment represented by the formula, is contained in the same layer together with the above-mentioned charge transport material.
この際、電荷輸送物質としてポリビニルカルバゾールと
トリニトロフルオレノンからなる電荷移動錯化合物を用
いることができる。At this time, a charge transfer complex compound consisting of polyvinylcarbazole and trinitrofluorenone can be used as the charge transport substance.
この例の電子写真感光体は、前述の有機光導電体と電荷
移動錯化合物をテトラヒドロフランに溶解されたポリエ
ステル溶液中に分散させた後、被膜形成させて作成でき
る。The electrophotographic photoreceptor of this example can be prepared by dispersing the above-described organic photoconductor and charge transfer complex compound in a polyester solution dissolved in tetrahydrofuran, and then forming a film thereon.
いずれの電子写真感光体においても、用いる顔料は一般
式(1)で示されるジスアゾ顔料から選ばれる少なくと
も1種類の顔料を含有し、必要に応じて光吸収の異なる
顔料を組合せて使用して感光体の感度を高めたり、パン
クロマチックな感光体を得るなどの目的で一般式(1)
で示されるジスアゾ顔料を2種類以上組合せたり、また
は公知の染料顔料から選ばれた電荷発生物質と組合せて
使用することも可能である。In any of the electrophotographic photoreceptors, the pigment used contains at least one type of pigment selected from disazo pigments represented by the general formula (1), and if necessary, pigments with different light absorptions are used in combination to sensitize the material. General formula (1) is used for the purpose of increasing the sensitivity of the body or obtaining a panchromatic photoreceptor.
It is also possible to use a combination of two or more kinds of disazo pigments represented by the above, or a combination with a charge generating substance selected from known dye pigments.
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やCRTプリンターなど
の電子写真応用分野にも広く用いることができる。The electrophotographic photoreceptor of the present invention can be used not only in electrophotographic copying machines, but also in a wide range of electrophotographic applications such as laser printers and CRT printers.
[実施例]
実施例1
アルミ板上にカゼインのアンモニア水溶液(カゼイン1
1.2g、28%アンモニア水1g、水222 li)
をマイヤーバーで乾燥後の膜厚が1.0pmとなるよう
に塗布し、乾燥した。[Example] Example 1 Ammonia aqueous solution of casein (casein 1
1.2 g, 28% ammonia water 1 g, water 222 li)
was applied with a Mayer bar so that the film thickness after drying was 1.0 pm, and dried.
次に、前記例示顔料(7)の有機光導電体5gを、エタ
ノール95+JLにブチラール樹脂(ブチラール化度6
3モル%)2gを溶解した液に加え、アトライターで2
時間分散した。この分散液を先に形成したカゼイン層の
上に乾燥後の膜厚が0.5JLmとなるようにマイヤー
バーで塗布し、乾燥して電荷発生層を形成した。Next, 5 g of the organic photoconductor of the exemplified pigment (7) was added to ethanol 95+JL with butyral resin (butyralization degree 6).
Add 2 g of 3 mol%) to the solution and add 2 g with an attritor
Spread out time. This dispersion was applied onto the previously formed casein layer using a Mayer bar so that the film thickness after drying was 0.5 JLm, and dried to form a charge generation layer.
のヒドラゾン化合物5gとポリメチルメタクリレート(
数平均分子量10万)5gをベンゼン70rslに溶解
し、これを電荷発生層の上に乾燥後の膜厚が12pmと
なるようにマイヤーバーチ塗布し、乾燥して電荷輸送層
を形成した。5g of hydrazone compound and polymethyl methacrylate (
5 g (number average molecular weight: 100,000) was dissolved in 70 rsl of benzene, and this was coated with Mayer birch onto the charge generation layer so that the film thickness after drying was 12 pm, and dried to form a charge transport layer.
こうして作成した電子写真感光体を静電複写紙試験装置
[5P−428(ターンテーブル)]を用いてスタチッ
ク方式で一5KVでコロナ帯電し、暗所で1秒間保持し
た後、照度2文UXで露光し、帯電特性を調べた。The electrophotographic photoreceptor thus prepared was statically charged with corona at 15 KV using an electrostatic copying paper tester [5P-428 (turntable)], held in a dark place for 1 second, and then set at an illuminance of 2 cm UX. It was exposed to light and its charging characteristics were examined.
帯電特性としては1表面型位(Vo )と1秒間暗減衰
させた時の電位をl/2に減衰するに必要な露光量(E
l/2)を測定した。The charging characteristics are 1 surface level (Vo) and the exposure amount (E) required to attenuate the potential to 1/2 when dark decayed for 1 second.
l/2) was measured.
さらに、繰り返し使用した時の明部電位と暗部電位の変
動を測定するために、上記作成した電子写真感光体を−
5,6KVのコロナ帯電器、露光量5文ux、secを
有する露光光学系、現像器、転写帯電器、除電露光光学
系およびクリーナーを備えた電子写真複写機のシリンダ
ーに貼り付けた。この複写機はシリンダーの駆動に伴い
転写紙上に画像が得られる構成になっている。Furthermore, in order to measure the fluctuations in bright area potential and dark area potential when repeatedly used, the electrophotographic photoreceptor prepared above was used.
It was attached to the cylinder of an electrophotographic copying machine equipped with a 5.6 KV corona charger, an exposure optical system with an exposure amount of 5 mux, sec, a developing device, a transfer charger, a static elimination exposure optical system, and a cleaner. This copying machine is configured to produce an image on transfer paper as a cylinder is driven.
この複写機を用いて、初期の明部電位(VL )と暗部
電位(VD )および5.000回使用した後の明部電
位(vL )と暗部電位CVo )を測定した。この結
果を示す。Using this copying machine, the initial bright area potential (VL) and dark area potential (VD) and the bright area potential (vL) and dark area potential (CVo) after 5,000 uses were measured. The results are shown below.
voニー610V、
El/2 : 3.0JLux、sec初 期
5千枚耐久後
実施例2〜15
実施例1で用いた例示顔料に代えて、下記の例示顔料を
用いた他は、全〈実施例1と同様の方法で電子写真感光
体を作成した。Vony 610V, El/2: 3.0JLux, early sec
Examples 2 to 15 after 5,000-sheet durability Electrophotographic photoreceptors were prepared in the same manner as in Example 1, except that the following exemplified pigments were used in place of the exemplified pigments used in Example 1.
各感光体の帯電特性と耐久特性を実施例1と同様の方法
によって測定した。The charging characteristics and durability characteristics of each photoreceptor were measured in the same manner as in Example 1.
結果を示す。Show the results.
2 (、1) 3 (3)2
600 2.73
610 2.94 61
0 3.25 615
3.16 610
3.37 Boo
2.88 605 2
、 79 610 ’
3.210 620 3.4
11 610 3.01 2
600 2 、 813
620 3.214
620 3.315
625 3.1実施例16
実施例1で作成した電荷発生層の上に、2,4.7−)
!Jニトロー9−フルオレノン5gとポリ−4,4−ジ
オキシジフェニル−2,2−プロパンカーボネート(分
子量30万)5gをテトラヒドロフラン70m1に溶解
して調製した塗布液を乾燥後の塗工量が10g7m2と
なるように塗布し、乾燥した。2 (,1) 3 (3)2
600 2.73
610 2.94 61
0 3.25 615
3.16 610
3.37 Boo
2.88 605 2
, 79 610'
3.210 620 3.4
11 610 3.01 2
600 2, 813
620 3.214
620 3.315
625 3.1 Example 16 On the charge generation layer prepared in Example 1, 2,4.7-)
! A coating solution prepared by dissolving 5 g of J Nitro 9-fluorenone and 5 g of poly-4,4-dioxydiphenyl-2,2-propane carbonate (molecular weight 300,000) in 70 ml of tetrahydrofuran has a coating amount of 10 g 7 m2 after drying. Apply it and let it dry.
こうして作成した電子写真感光体を実施例1と同様の方
法で帯電特性を測定した。このとき帯電は十とした。結
果を示す。The charging characteristics of the electrophotographic photoreceptor thus prepared were measured in the same manner as in Example 1. At this time, the charge was set to 10. Show the results.
vo :+600V、
El/2:8.3JluX、see、
初 期
VD :+805V、 VL :+40V5千枚耐久後
Vo : +625V、VL : +80V実施例
17
アルミ蒸着ポリエチレンテレフタレートフィルムのアル
ミ面上に膜厚1.OILmのポリビニルアルコールの被
膜を形成した。vo: +600V, El/2: 8.3JluX, see, initial VD: +805V, VL: +40V After 5,000 sheets durability Vo: +625V, VL: +80V Example 17 Film thickness 1 on the aluminum surface of aluminum vapor-deposited polyethylene terephthalate film .. A polyvinyl alcohol film of OILm was formed.
次に、実施例1で用いた例示顔料(7)の分散液を先に
形成したポリビニルアルコール層上に、乾燥後の膜厚が
0.5ルmとなるようにマイヤーバーで塗布し、乾燥し
て電荷発生層を形成した。Next, the dispersion of the exemplary pigment (7) used in Example 1 was applied onto the previously formed polyvinyl alcohol layer using a Mayer bar so that the film thickness after drying was 0.5 lm, and then dried. A charge generation layer was formed.
次いで1−[キノリル(2)]−3−(p−ジエチルア
ミノスチリル)−5−(p−ジエチルアミノフェニル)
ピラゾリンを5gとボリアリレート樹脂(ビスフェノー
ルAとテレフタル酸−イソフタル酸の11重合体)5g
をテトラヒドロフラン70m文に溶解した液を電荷発生
層の上に乾燥後の膜厚がloILmとなるように塗布し
、乾燥して電荷輸送層を形成した。Then 1-[quinolyl(2)]-3-(p-diethylaminostyryl)-5-(p-diethylaminophenyl)
5g of pyrazoline and 5g of polyarylate resin (11 polymers of bisphenol A and terephthalic acid-isophthalic acid)
A solution obtained by dissolving 100 ml of 100 ml of tetrahydrofuran in 70 ml of tetrahydrofuran was applied onto the charge generating layer so that the film thickness after drying was loILm, and dried to form a charge transporting layer.
こうして作成した電子写真感光体について帯電特性およ
び耐久特性を実施例1と同様の方法で測定した。結果を
示す。The charging characteristics and durability characteristics of the electrophotographic photoreceptor thus prepared were measured in the same manner as in Example 1. Show the results.
voニー620V。VONY 620V.
El/2 : 3.2JLux、sec。El/2: 3.2JLux, sec.
初 期
Vo ニー620V、 VL ニー35V5千枚耐久後
VDニー655V、VLニー75V
実施例18
厚さ100.gmのアルミ板上にカゼインのアンモニア
水溶液を塗布し、乾燥して膜厚1.OILmの下引層を
形成した。Initial Vo knee 620V, VL knee 35V, after 5,000 sheets durability VD knee 655V, VL knee 75V Example 18 Thickness 100. An ammonia aqueous solution of casein is applied onto a GM aluminum plate and dried to a film thickness of 1. A subbing layer of OILm was formed.
次に、2,4.7−)ジニトロ−9−フルオレノン5g
とポリ−N−ビニルカルバゾール(数平均分子量30万
)5gをテトラヒドロフラン70rsnに溶解して電荷
移動錯化合物を調製した。Next, 5 g of 2,4.7-)dinitro-9-fluorenone
A charge transfer complex compound was prepared by dissolving 5 g of poly-N-vinylcarbazole (number average molecular weight: 300,000) in 70 rsn of tetrahydrofuran.
この電荷移動錯化合物と例示顔料(19)の光導電体1
gを、ポリエステル樹脂5gをテトラヒドロフラン70
rrrlに溶解した液に加え、分散した。この分散液を
下引層の上に乾燥後の膜厚が12JLmとなるように塗
布し、乾燥した。Photoconductor 1 of this charge transfer complex compound and exemplary pigment (19)
g, 5 g of polyester resin and 70 g of tetrahydrofuran.
It was added to the solution dissolved in rrrl and dispersed. This dispersion was applied onto the undercoat layer so that the film thickness after drying was 12 JLm, and dried.
こうして作成した電子写真感光体の帯電特性を実施例1
と同様の方法で測定した。Example 1 Charging characteristics of the electrophotographic photoreceptor thus prepared
It was measured in the same manner as.
但し、帯電極性は十とした。結果を示す。However, the charging polarity was set to 10. Show the results.
vo :+615V。vo: +615V.
E 1/2 : 6 、5立ux、sec。E 1/2: 6, 5 ux, sec.
[発明の効果]
本発明の電子写真感光体は特定構造のジスアゾ顔料を感
光層に用いることにより、当該ジスアゾ顔料を含む感光
層内部におけるキャリア発生効率ないしはキャリア輸送
効率のいずれか一方ないし双方が良くなることが推定さ
れ、高感度で耐久使用時における電位安定性に優れた顕
著な効果を奏する。[Effects of the Invention] By using a disazo pigment with a specific structure in the photosensitive layer, the electrophotographic photoreceptor of the present invention can improve carrier generation efficiency, carrier transport efficiency, or both in the photosensitive layer containing the disazo pigment. It is estimated that this will result in high sensitivity and excellent potential stability during long-term use.
Claims (3)
1)で示されるジスアゾ顔料の少なくとも一種を光導電
体として含有することを特徴とする電子写真感光体。 一般式(1) ▲数式、化学式、表等があります▼ 式中、Aはフェノール性OH基を有するカップラー残基
または2−メチルインドレニン誘導体のカップラー残基
を示す。(1) The following general formula (
An electrophotographic photoreceptor comprising at least one of the disazo pigments shown in 1) as a photoconductor. General formula (1) ▲ Numerical formulas, chemical formulas, tables, etc. are available▼ In the formula, A represents a coupler residue having a phenolic OH group or a coupler residue of a 2-methylindolenine derivative.
般式(2)〜(8)で示される基から選ばれるカップラ
ー残基である特許請求の範囲第1項記載の電子写真感光
体。 一般式 ▲数式、化学式、表等があります▼(2) ▲数式、化学式、表等があります▼(3)▲数式、化学
式、表等があります▼(4) ▲数式、化学式、表等があります▼(5)▲数式、化学
式、表等があります▼(6) ▲数式、化学式、表等があります▼(7) ▲数式、化学式、表等があります▼(8) 式中、R_1およびR_2は水素原子、置換基を有して
もよいアルキル基、アラルキル基、アリール基、ヘテロ
環基、イミノ基あるいはR_1、R_2の結合する窒素
原子と一緒に環状アミノ基を示し、Xはベンゼン環と縮
合して多環芳香環あるいはヘテロ環を形成する残基を示
し、R_3およびR_4は置換基を有してもよいアルキ
ル基、アラルキル基あるいはアリール基を示し、Yは芳
香族炭化水素の2価の基あるいは窒素原子と共にヘテロ
環を形成する2価の基を示し、R_5およびR_6は水
素原子、アルキル基、アルコキシ基、ハロゲン原子、シ
アノ基あるいはニトロ基を示す。(2) The electrophotographic photoreceptor according to claim 1, wherein the coupler residue A in the general formula (1) is a coupler residue selected from the groups represented by the following general formulas (2) to (8). General formulas ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (2) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (3) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (4) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼(5) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (6) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (7) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (8) In the formula, R_1 and R_2 are A hydrogen atom, an alkyl group that may have a substituent, an aralkyl group, an aryl group, a heterocyclic group, an imino group, or a cyclic amino group together with the nitrogen atom to which R_1 and R_2 are bonded, and X is fused with a benzene ring. represents a residue forming a polycyclic aromatic ring or a heterocycle, R_3 and R_4 represent an alkyl group, an aralkyl group, or an aryl group that may have a substituent, and Y represents a divalent aromatic hydrocarbon. It represents a divalent group that forms a heterocycle with a group or a nitrogen atom, and R_5 and R_6 represent a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, a cyano group, or a nitro group.
積層型感光層であり、該電荷発生層に前記一般式(1)
で示されるジスアゾ顔料を含有する特許請求の範囲第1
項記載の電子写真感光体。(3) The photosensitive layer is a laminated photosensitive layer consisting of a charge generation layer and a charge transport layer, and the charge generation layer has the general formula (1).
Claim 1 containing a disazo pigment represented by
The electrophotographic photoreceptor described in .
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP1133487A JPS63180960A (en) | 1987-01-22 | 1987-01-22 | Electrophotographic sensitive body |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP1133487A JPS63180960A (en) | 1987-01-22 | 1987-01-22 | Electrophotographic sensitive body |
Publications (1)
Publication Number | Publication Date |
---|---|
JPS63180960A true JPS63180960A (en) | 1988-07-26 |
Family
ID=11775134
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP1133487A Pending JPS63180960A (en) | 1987-01-22 | 1987-01-22 | Electrophotographic sensitive body |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS63180960A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20160126040A (en) | 2014-03-26 | 2016-11-01 | 후지필름 가부시키가이샤 | Organic transistor, compound, organic semiconductor material for non-light-emitting organic semiconductor device, material for organic transistor, coating liquid for non-light-emitting organic semiconductor device, method for manufacturing organic transistor, method for manufacturing organic semiconductor film, organic semiconductor film for non-light-emitting organic semiconductor device, and method for synthesizing organic semiconductor material |
-
1987
- 1987-01-22 JP JP1133487A patent/JPS63180960A/en active Pending
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20160126040A (en) | 2014-03-26 | 2016-11-01 | 후지필름 가부시키가이샤 | Organic transistor, compound, organic semiconductor material for non-light-emitting organic semiconductor device, material for organic transistor, coating liquid for non-light-emitting organic semiconductor device, method for manufacturing organic transistor, method for manufacturing organic semiconductor film, organic semiconductor film for non-light-emitting organic semiconductor device, and method for synthesizing organic semiconductor material |
US10270043B2 (en) | 2014-03-26 | 2019-04-23 | Fujifilm Corporation | Organic transistor, compound, organic semiconductor material for non-light-emitting organic semiconductor device, material for organic transistor, coating solution for non-light-emitting organic semiconductor device, method for manufacturing organic transistor, method for manufacturing organic semiconductor film, organic semiconductor film for non-light-emitting organic semiconductor device, and method for synthesizing organic semiconductor material |
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