JPS6050539A - Electrophotographic sensitive body - Google Patents
Electrophotographic sensitive bodyInfo
- Publication number
- JPS6050539A JPS6050539A JP58157912A JP15791283A JPS6050539A JP S6050539 A JPS6050539 A JP S6050539A JP 58157912 A JP58157912 A JP 58157912A JP 15791283 A JP15791283 A JP 15791283A JP S6050539 A JPS6050539 A JP S6050539A
- Authority
- JP
- Japan
- Prior art keywords
- phthalocyanine
- layer
- charge generating
- charge
- parts
- 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.)
- Granted
Links
- 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 claims abstract description 63
- 239000000463 material Substances 0.000 claims abstract description 19
- 239000000126 substance Substances 0.000 claims abstract description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 2
- 108091008695 photoreceptors Proteins 0.000 claims description 29
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 150000007522 mineralic acids Chemical class 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000006575 electron-withdrawing group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000001174 sulfone group Chemical group 0.000 claims description 3
- 238000000034 method Methods 0.000 abstract description 25
- 239000000203 mixture Substances 0.000 abstract description 13
- 230000035945 sensitivity Effects 0.000 abstract description 11
- 239000011230 binding agent Substances 0.000 abstract description 10
- 239000002253 acid Substances 0.000 abstract description 6
- 230000008569 process Effects 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract description 3
- 239000000758 substrate Substances 0.000 abstract 2
- 229910006069 SO3H Inorganic materials 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 230000006698 induction Effects 0.000 abstract 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 49
- 229920005989 resin Polymers 0.000 description 18
- 239000011347 resin Substances 0.000 description 18
- 230000032258 transport Effects 0.000 description 18
- 238000000576 coating method Methods 0.000 description 11
- 239000011248 coating agent Substances 0.000 description 9
- -1 heterocyclic nitro compounds Chemical class 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 229920000178 Acrylic resin Polymers 0.000 description 5
- 239000004925 Acrylic resin Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- WUPHOULIZUERAE-UHFFFAOYSA-N 3-(oxolan-2-yl)propanoic acid Chemical compound OC(=O)CCC1CCCO1 WUPHOULIZUERAE-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- 229910052980 cadmium sulfide Inorganic materials 0.000 description 4
- 239000010408 film Substances 0.000 description 4
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 4
- 239000011669 selenium Substances 0.000 description 4
- 229910052711 selenium Inorganic materials 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- 229920000877 Melamine resin Polymers 0.000 description 3
- 239000004640 Melamine resin Substances 0.000 description 3
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Chemical group C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 3
- 206010070834 Sensitisation Diseases 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical group CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 239000003822 epoxy resin Substances 0.000 description 3
- 238000004898 kneading Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- XQZYPMVTSDWCCE-UHFFFAOYSA-N phthalonitrile Chemical group N#CC1=CC=CC=C1C#N XQZYPMVTSDWCCE-UHFFFAOYSA-N 0.000 description 3
- 229920005668 polycarbonate resin Polymers 0.000 description 3
- 239000004431 polycarbonate resin Substances 0.000 description 3
- 229920000647 polyepoxide Polymers 0.000 description 3
- 229920001225 polyester resin Polymers 0.000 description 3
- 239000004645 polyester resin Substances 0.000 description 3
- 230000008313 sensitization Effects 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- 239000011787 zinc oxide Substances 0.000 description 3
- TURIHPLQSRVWHU-UHFFFAOYSA-N 2-phenylnaphthalene Chemical compound C1=CC=CC=C1C1=CC=C(C=CC=C2)C2=C1 TURIHPLQSRVWHU-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical compound O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 description 2
- HAPOJKSPCGLOOD-UHFFFAOYSA-N Benzo[b]fluorene Chemical compound C1=CC=C2C=C3CC4=CC=CC=C4C3=CC2=C1 HAPOJKSPCGLOOD-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 229920002433 Vinyl chloride-vinyl acetate copolymer Polymers 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 238000003475 lamination Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical group OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000728 polyester Polymers 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
- 229920002545 silicone oil Polymers 0.000 description 2
- 229920002050 silicone resin Polymers 0.000 description 2
- 238000007613 slurry method Methods 0.000 description 2
- 238000004544 sputter deposition Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- QKLPIYTUUFFRLV-YTEMWHBBSA-N 1,4-bis[(e)-2-(2-methylphenyl)ethenyl]benzene Chemical compound CC1=CC=CC=C1\C=C\C(C=C1)=CC=C1\C=C\C1=CC=CC=C1C QKLPIYTUUFFRLV-YTEMWHBBSA-N 0.000 description 1
- VEUMBMHMMCOFAG-UHFFFAOYSA-N 2,3-dihydrooxadiazole Chemical compound N1NC=CO1 VEUMBMHMMCOFAG-UHFFFAOYSA-N 0.000 description 1
- ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- RZVCEPSDYHAHLX-UHFFFAOYSA-N 3-iminoisoindol-1-amine Chemical compound C1=CC=C2C(N)=NC(=N)C2=C1 RZVCEPSDYHAHLX-UHFFFAOYSA-N 0.000 description 1
- MCGBIXXDQFWVDW-UHFFFAOYSA-N 4,5-dihydro-1h-pyrazole Chemical compound C1CC=NN1 MCGBIXXDQFWVDW-UHFFFAOYSA-N 0.000 description 1
- CLQYLLIGYDFCGY-UHFFFAOYSA-N 4-(2-anthracen-9-ylethenyl)-n,n-diethylaniline Chemical compound C1=CC(N(CC)CC)=CC=C1C=CC1=C(C=CC=C2)C2=CC2=CC=CC=C12 CLQYLLIGYDFCGY-UHFFFAOYSA-N 0.000 description 1
- YHELYTRELJRMBS-UHFFFAOYSA-N 4-(9H-fluoren-2-yldiazenyl)-3-methylphenol Chemical compound C1=C(C=CC=2C3=CC=CC=C3CC1=2)N=NC=1C(=CC(=CC=1)O)C YHELYTRELJRMBS-UHFFFAOYSA-N 0.000 description 1
- MNFZZNNFORDXSV-UHFFFAOYSA-N 4-(diethylamino)benzaldehyde Chemical compound CCN(CC)C1=CC=C(C=O)C=C1 MNFZZNNFORDXSV-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
- 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
- PLAZXGNBGZYJSA-UHFFFAOYSA-N 9-ethylcarbazole Chemical compound C1=CC=C2N(CC)C3=CC=CC=C3C2=C1 PLAZXGNBGZYJSA-UHFFFAOYSA-N 0.000 description 1
- VIJYEGDOKCKUOL-UHFFFAOYSA-N 9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 VIJYEGDOKCKUOL-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
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 229910052692 Dysprosium Inorganic materials 0.000 description 1
- 229910052691 Erbium Inorganic materials 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
- 229910052689 Holmium Inorganic materials 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 229910052765 Lutetium Inorganic materials 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical group O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- 229910052779 Neodymium Inorganic materials 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 229910052772 Samarium Inorganic materials 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-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
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- XBDYBAVJXHJMNQ-UHFFFAOYSA-N Tetrahydroanthracene Natural products C1=CC=C2C=C(CCCC3)C3=CC2=C1 XBDYBAVJXHJMNQ-UHFFFAOYSA-N 0.000 description 1
- 229910052776 Thorium Inorganic materials 0.000 description 1
- 229910052775 Thulium Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 229910052770 Uranium Inorganic materials 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical class NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- VJBORWDCKOLYLT-UHFFFAOYSA-N [N+](=O)([O-])[Cu][N+](=O)[O-] Chemical compound [N+](=O)([O-])[Cu][N+](=O)[O-] VJBORWDCKOLYLT-UHFFFAOYSA-N 0.000 description 1
- BJUKBQYOYJOPDS-UHFFFAOYSA-N [O-][N+]([Cu])=O Chemical compound [O-][N+]([Cu])=O BJUKBQYOYJOPDS-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 229910021529 ammonia Inorganic materials 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
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Chemical class 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- IOMXCGDXEUDZAK-UHFFFAOYSA-N chembl1511179 Chemical compound OC1=CC=C2C=CC=CC2=C1N=NC1=NC=CS1 IOMXCGDXEUDZAK-UHFFFAOYSA-N 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- KBQHZAAAGSGFKK-UHFFFAOYSA-N dysprosium atom Chemical compound [Dy] KBQHZAAAGSGFKK-UHFFFAOYSA-N 0.000 description 1
- QELUYTUMUWHWMC-UHFFFAOYSA-N edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 description 1
- UYAHIZSMUZPPFV-UHFFFAOYSA-N erbium Chemical compound [Er] UYAHIZSMUZPPFV-UHFFFAOYSA-N 0.000 description 1
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 229910052735 hafnium Inorganic materials 0.000 description 1
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- KJZYNXUDTRRSPN-UHFFFAOYSA-N holmium atom Chemical compound [Ho] KJZYNXUDTRRSPN-UHFFFAOYSA-N 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- OHSVLFRHMCKCQY-UHFFFAOYSA-N lutetium atom Chemical compound [Lu] OHSVLFRHMCKCQY-UHFFFAOYSA-N 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- VLAPMBHFAWRUQP-UHFFFAOYSA-L molybdic acid Chemical compound O[Mo](O)(=O)=O VLAPMBHFAWRUQP-UHFFFAOYSA-L 0.000 description 1
- JGOAZQAXRONCCI-SDNWHVSQSA-N n-[(e)-benzylideneamino]aniline Chemical compound C=1C=CC=CC=1N\N=C\C1=CC=CC=C1 JGOAZQAXRONCCI-SDNWHVSQSA-N 0.000 description 1
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 1
- QHADMMAFBAZFTE-UHFFFAOYSA-N naphtho[2,1,8-def]quinoline Chemical compound C1=CN=C2C=CC3=CC=CC4=CC=C1C2=C43 QHADMMAFBAZFTE-UHFFFAOYSA-N 0.000 description 1
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 229920006287 phenoxy resin Polymers 0.000 description 1
- 239000013034 phenoxy resin Substances 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 125000005543 phthalimide group Chemical group 0.000 description 1
- 229920006391 phthalonitrile polymer Polymers 0.000 description 1
- 230000000704 physical effect Effects 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
- 229920002647 polyamide Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 229960005265 selenium sulfide Drugs 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-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
- 229920001169 thermoplastic Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- DNYWZCXLKNTFFI-UHFFFAOYSA-N uranium Chemical compound [U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U] DNYWZCXLKNTFFI-UHFFFAOYSA-N 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
- 229940075420 xanthine Drugs 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 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
- G03G5/0696—Phthalocyanines
Abstract
Description
【発明の詳細な説明】
本発明は導電性支持体上に電荷発生層および電荷輸送層
を形成してなる電子写真感光体に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to an electrophotographic photoreceptor comprising a charge generation layer and a charge transport layer formed on a conductive support.
一般に電子写真方式にはゼログラフィ一方式のごとくセ
レン、硫化カドミウムなどの光導電体素子を金属ドラム
上に薄膜状に形成した感光体を暗所にて帯電させ、光像
を照射（露光）シ。Generally, in electrophotography, a photoreceptor is formed by forming a thin film of photoconductor elements such as selenium or cadmium sulfide on a metal drum, as in xerography, which is charged in a dark place, and a light image is irradiated (exposed) to the photoreceptor. .
静電潜像を形成させた後、トナーにより可視像を作り（
現像）、これを紙等に転写定着する方法、あるいはエレ
クトロファックス方式のように光導電性層（感光層）を
紙上に設け、この感光体上に帯電、露光、現像および定
着により光導電性層上に永久可視像を得る方法がある。After forming an electrostatic latent image, a visible image is created using toner (
development), transferring and fixing this onto paper, etc., or providing a photoconductive layer (photosensitive layer) on paper as in the electrofax method, and forming a photoconductive layer on this photoreceptor by charging, exposing, developing and fixing. Above is a method to obtain a permanently visible image.
電子写真感光体の光導電体材料として現在広く用いられ
ているものに、無機化合物として無定形セレン、硫化カ
ドミウム、酸化亜鉛等がある。無定形セレンは光導電体
材料としての特性は良好であるが、製法が蒸着によらね
ばならず製造がむずかしく、蒸着膜は可撓性がなく、シ
かも毒性が強いため、その取り扱いに注意を要し、また
高価であるという欠点がある。硫化カドミ＋ム、酸化亜
鉛は結着剤樹脂に分散させた光導電性層の形で用いられ
るが、樹脂／光導電体材料の重量比が０．２〜０．３以
下でないと実用性のある感度が得られないため、可撓性
、平滑度、硬度、引張り強度、耐摩擦性などの機械的な
性質に欠点を有する。したがって、そのままでは反復使
用に耐えることができない。硫化カドミウムには衛生性
の問題にも考慮が必要である。Inorganic compounds that are currently widely used as photoconductor materials for electrophotographic photoreceptors include amorphous selenium, cadmium sulfide, and zinc oxide. Amorphous selenium has good properties as a photoconductor material, but it is difficult to manufacture because it must be manufactured by vapor deposition, and the vapor-deposited film is not flexible and is highly toxic, so it must be handled with care. It has the disadvantage of being expensive and time consuming. Cadmium sulfide and zinc oxide are used in the form of a photoconductive layer dispersed in a binder resin, but it is not practical unless the resin/photoconductor material weight ratio is less than 0.2 to 0.3. Since a certain sensitivity cannot be obtained, it has drawbacks in mechanical properties such as flexibility, smoothness, hardness, tensile strength, and abrasion resistance. Therefore, it cannot withstand repeated use as it is. Hygiene issues with cadmium sulfide also need to be considered.
一部、有機化合物としてはポリビニルカルバゾール（Ｐ
ＶＫ）、 フタロシアニン等が知られている。これらの
光導電体材料は可撓性、加工性に優れるが、単独では電
子写真感度の点で実用に供したとき十分でなく、さらに
化学増感。Some organic compounds include polyvinylcarbazole (P
VK), phthalocyanine, etc. are known. Although these photoconductor materials have excellent flexibility and processability, they do not have sufficient electrophotographic sensitivity for practical use when used alone, and chemical sensitization is required.
光学増感の手段を併用することによって増感される。化
学増感剤としては、２．４．７−）リニトロー９−フル
オレノン（ＴＮＦ）、２，４．５．７−テトラニトロ−
９−フルオレノン（ＴＥＮＦ）などの多環もしくは複素
環ニトロ化合物、アントラキノンなどのキノン類、およ
びテトラシアノエチレンなどのニトリル化合物などが知
られている。また光学増感剤としては。Sensitization is achieved through the combined use of optical sensitization means. Chemical sensitizers include 2.4.7-)linitro-9-fluorenone (TNF), 2,4.5.7-tetranitro-
Polycyclic or heterocyclic nitro compounds such as 9-fluorenone (TENF), quinones such as anthraquinone, and nitrile compounds such as tetracyanoethylene are known. Also as an optical sensitizer.
キサンチン系染料、キノリン系染料が知られている。し
かし、これらの物質を電子写真感光体用に実用に供する
感度が得られるまで添加すると、これらの物質自身が耐
帯電性、耐光性等に問題があるため、連続帯電、Ｕ光に
よる疲労現象が著しく、実用上問題がある。また、化学
増感剤としてＴＮＦ、ＴＥＮＦは特にすぐれた増感効果
をもたらし、実際、有機光導電体等に対し、よく使用さ
れているものである。しかし。Xanthine dyes and quinoline dyes are known. However, if these substances are added to an electrophotographic photoreceptor until a practical level of sensitivity is obtained, these substances themselves have problems with charging resistance, light resistance, etc., and fatigue phenomena due to continuous charging and U light may occur. This poses a significant practical problem. Further, as chemical sensitizers, TNF and TENF have particularly excellent sensitizing effects, and are actually often used for organic photoconductors and the like. but.
これらの物質の価格は高価であり、実用上必要な感度を
得るため、多量にこれらの物質を加えると、感光体は価
格上の点だけでなく、さらに衛生上の問題があり、使用
に際し疑念が持たれる。These substances are expensive, and adding large amounts of these substances to obtain the sensitivity required for practical use will not only increase the price of the photoreceptor, but also pose hygiene problems and raise concerns about its use. is held.
また、フタロシアニンに対しフタロシアニン誘導体を使
用する方法も一部では検討されている。この方法では強
力な機械的混合処理を必要とするものであり、確かにこ
の方法によってフタロシアニンとフタロシアニン誘導体
とが均一に混合され、電子写真特性の優れた電子写真感
光体が得られるが、かなり長時間に及ぶ機械的混合処理
は多大な労力を必要とするものであり。In addition, some studies are also considering methods of using phthalocyanine derivatives for phthalocyanine. This method requires a strong mechanical mixing process, and it is true that this method allows the phthalocyanine and phthalocyanine derivative to be mixed uniformly, resulting in an electrophotographic photoreceptor with excellent electrophotographic properties, but it takes quite a long time. The time-consuming mechanical mixing process is labor-intensive.
この方法の実施は、工業上大きな制約を受ける。さらに
、電子写真感光体として要求される物性を、必ずしも十
分病たしているとは言えない点も見られる。The implementation of this method is subject to significant industrial constraints. Furthermore, it can be seen that the physical properties required for an electrophotographic photoreceptor are not necessarily sufficiently improved.
一部１機能分離型積層感光体として、導電性支持体上に
、電荷発生層および電荷輸送層を形成する手段も種々検
討されている。この積層感光体には導電性支持体に電荷
発生層／電荷輸送層、または積層順を変えて電荷発生層
／電荷輸送層を形成するものが知られている。この積層
感光体は、一般に単層感光体に見られるような発生電荷
のトラップへの捕捉に起因するインダクシｅン効果が減
少し１階調性が良くなる利点を有している。Various means for forming a charge generation layer and a charge transport layer on a conductive support have also been studied as a laminated photoreceptor of which one function is partially separated. Known laminated photoreceptors include those in which a charge generation layer/charge transport layer is formed on a conductive support, or a charge generation layer/charge transport layer is formed by changing the lamination order. This laminated photoreceptor has the advantage that the inductance effect caused by the trapping of generated charges, which is generally observed in single-layer photoreceptors, is reduced and one-level gradation is improved.
本発明は特定のフタロシアニン系電荷発生材料を用いた
電荷発生層とすることにより２階調性は勿論、感度等の
電子写真特性に優れた機能分離型積層感光体を提供する
ものである。The present invention provides a functionally separated laminated photoreceptor which has excellent electrophotographic properties such as sensitivity as well as two-tone property by using a specific phthalocyanine-based charge generating material as a charge generating layer.
すなわち、フタロシアニンおよびフタロシアニン分子の
ベンゼン核がニトロ基、シアノ斌。That is, the benzene nucleus of phthalocyanine and phthalocyanine molecules is a nitro group and a cyano group.
ハロゲン原子、スルホン基およびカルボキシル基から選
ばれる少なくとも１種の電子吸引性基によって置換され
たフタロシアニン誘導体を。A phthalocyanine derivative substituted with at least one electron-withdrawing group selected from a halogen atom, a sulfone group, and a carboxyl group.
フタロシアニンと塩を形成し得る無機酸と混合した後、
水もしくは塩基性物質によって析出せしめて得られた電
荷発生材料を含む層（電荷発生層）および電荷輸送層を
導電性支持体上に形成してなる電子写真感光体である。After mixing with an inorganic acid that can form a salt with the phthalocyanine,
This is an electrophotographic photoreceptor in which a layer containing a charge-generating material (charge-generating layer) obtained by precipitation with water or a basic substance and a charge-transporting layer are formed on a conductive support.
本発明に係わるフタロシアニンとしては無金属フタロシ
アニンまたは金属フタロシアニン。The phthalocyanine according to the present invention is metal-free phthalocyanine or metal phthalocyanine.
あるいはこれらの混合物である。金属フタロシアニンの
金属としては銅、銀、ベリリウム、マグネシウム、カル
シウム、亜鉛、カドミウム。Or a mixture of these. Metals of metal phthalocyanine include copper, silver, beryllium, magnesium, calcium, zinc, and cadmium.
バリウム、水銀、アルミニウム、ガリウム、インジウム
、ランタン、ネオジム、サマリウム。Barium, mercury, aluminum, gallium, indium, lanthanum, neodymium, samarium.
ユーロピウム、ガドリニウム、ジスプロシウム、ホルミ
ウム、エルビウム、ツリウム、イッテルビウム、ルテチ
ウム、チタン、錫、ハフニウム、鉛、トリウム、バナジ
ウム、アンチモン。Europium, gadolinium, dysprosium, holmium, erbium, thulium, ytterbium, lutetium, titanium, tin, hafnium, lead, thorium, vanadium, antimony.
クロム、モリブデン、ウラン、マンガン、鉄。Chromium, molybdenum, uranium, manganese, iron.
コバルト、ニッケル、ロジウム、パラジウム。Cobalt, nickel, rhodium, palladium.
オスミウム、および白金等である。また、フタロシアニ
ンの中心核として金属原子ではなく。These include osmium and platinum. Moreover, rather than a metal atom as the central nucleus of phthalocyanine.
３価以上の原子価を有するハロゲン化金属であってもよ
い。無金属フタロシアニンや銅、コバルト、鉛、亜鉛等
の金属フタロシアニンが好ましい。さらに、低ハロゲン
化フタロシアニンであってもよい。なお、フタロシアニ
ンは顔料としてよく知られている化合物であるが１本発
明において、どのような製法によって得られたフタロシ
アニンでもよく、顔料において知られているように、ク
ルードと称されているフタロシアニンは勿論、顔料化さ
れたフタロシアニンを用いてもよい。It may be a metal halide having a valence of 3 or more. Metal-free phthalocyanines and metal phthalocyanines such as copper, cobalt, lead, and zinc are preferred. Furthermore, it may be a low halogenated phthalocyanine. Although phthalocyanine is a well-known compound as a pigment, in the present invention, any phthalocyanine obtained by any manufacturing method may be used. , pigmented phthalocyanines may also be used.
本発明に係わるフタロシアニン誘導体としてはフタロシ
アニン分子のベンゼン核がニトロ基、シアノ基、ハロゲ
ン原子、スルホン基およびカルボキシル基から選ばれる
少なくとも１種の電子吸引性基によって置換されたもの
である。The phthalocyanine derivative according to the present invention is one in which the benzene nucleus of the phthalocyanine molecule is substituted with at least one electron-withdrawing group selected from a nitro group, a cyano group, a halogen atom, a sulfone group, and a carboxyl group.
このフタロシアニン誘導体はフタロシアニン合成時に、
フタロシアニンの原料となるフタロニトリル、フタル酸
、無水フタル酸、フタルイミドとして、上記置換基で置
換されたフタロニトリル、フタル酸、無水フタル酸、フ
タルイミドを用いること、もしくは一部併用することに
よって得られる。フタロシアニン誘導体の製法としては
特に制限されない、また、フタロシアニン誘導体１分子
における置換基の数としては１〜１６個、好ましくは１
〜８個、より好ましくは１〜４個である。置換基の数は
、製造法によって異なるが、数の異なるものが混合して
いる状態が多い。なお、フタロシアニン誘導体として９
例えばニトロ基およびシアノ基を有するもの、ニトロ基
を有するフタロシアニン誘導体およびシアノ基を有する
フタロシアニン誘導体を混合して使用してもよい。さら
に１本発明のフタロシアニン［１以外のフタロシアニン
誘導体を一部併用することもできる。This phthalocyanine derivative is used during phthalocyanine synthesis.
It can be obtained by using phthalonitrile, phthalic acid, phthalic anhydride, or phthalimide substituted with the above-mentioned substituents as the raw material for phthalocyanine, or by using some of them in combination. The method for producing the phthalocyanine derivative is not particularly limited, and the number of substituents in one molecule of the phthalocyanine derivative is 1 to 16, preferably 1.
-8 pieces, more preferably 1-4 pieces. The number of substituents varies depending on the manufacturing method, but different numbers of substituents are often mixed. In addition, as a phthalocyanine derivative, 9
For example, those having a nitro group and a cyano group, a phthalocyanine derivative having a nitro group, and a phthalocyanine derivative having a cyano group may be used in combination. Furthermore, a part of phthalocyanine derivatives other than the phthalocyanine of the present invention [1] may also be used in combination.
また、フタロシアニン誘導体のフタロシアニンとしては
無金属フタロシアニンまたは銅、ニッケル、コバルト、
鉄、ナトリウム、リチウム、カルシウム、マグネシウム
、アルミニウム等の金属フタロシアニンである。フタロ
シアニンとフタロシアニン誘導体との組成割合は、フタ
ロシアニン１００１１１部に対し、フタロシアニン誘導
体が０．０１〜２０重量部である。好ましくはフタロシ
アニン誘導体を０．１〜５重量部である。０．０１重量
部未満では十分な感度が得られず、また、２０重量部を
超えると、暗減衰率が増大し実用に供しえない。In addition, phthalocyanine derivatives include metal-free phthalocyanine or copper, nickel, cobalt,
Metal phthalocyanines such as iron, sodium, lithium, calcium, magnesium, and aluminum. The composition ratio of phthalocyanine and phthalocyanine derivative is 0.01 to 20 parts by weight of phthalocyanine derivative to 100,111 parts of phthalocyanine. Preferably, the amount of the phthalocyanine derivative is 0.1 to 5 parts by weight. If it is less than 0.01 parts by weight, sufficient sensitivity cannot be obtained, and if it exceeds 20 parts by weight, the dark decay rate increases and it cannot be put to practical use.
次に、フタロシアニンおよびフタロシアニン誘導体の製
造方法につき９代表的な例を挙げる。まずフタロジニト
リルおよびもしくはニトロ基やシアノ基によって置換さ
れたフタロジニトリルと金属塩の存在下または不存在下
、アンモニアアルコラードのような強塩基触媒とともに
、アルコール等の有機溶媒中で加熱するニトリル法、無
水フタル酸およびもしくはニトロ基やシアノ基によって
置換した無水フタル酸、尿素、金属塩をモリブデン酸、
アンモニウム等を触媒として溶媒の存在下もしくは不存
在下に加熱する方法がある。その他、アミノイミノイソ
インドレニン等を用いる方法でもよい。Next, nine representative examples of methods for producing phthalocyanine and phthalocyanine derivatives are listed. First, the nitrile is heated in an organic solvent such as an alcohol with a strong base catalyst such as ammonia alcoholade in the presence or absence of a phthalodinitrile and/or a phthalodinitrile substituted with a nitro group or a cyano group and a metal salt. method, phthalic anhydride and or phthalic anhydride substituted with nitro or cyano groups, urea, metal salts with molybdic acid,
There is a method of heating in the presence or absence of a solvent using ammonium or the like as a catalyst. Alternatively, a method using aminoiminoisoindolenine or the like may be used.
本発明に用いられるフタロシアニンと塩を形成し得る無
機酸としては、硫酸、オルトリン酸、ビロリン酸、クロ
ロスルホン酸、塩酸、ヨウ化水素酸、フッ化水素酸、臭
化水素酸等が用いられる。これら無機酸はフタロシアニ
ンのアシッドペースティング法、アシッドスラリー法等
の従来より知られている方法に使用されているものが−
用いられる。また、方法としても、従来より知られてい
る方法が適用される。例えば。Examples of inorganic acids that can form salts with the phthalocyanine used in the present invention include sulfuric acid, orthophosphoric acid, birophosphoric acid, chlorosulfonic acid, hydrochloric acid, hydroiodic acid, hydrofluoric acid, and hydrobromic acid. These inorganic acids are those used in conventionally known methods such as phthalocyanine acid pasting method and acid slurry method.
used. Further, as a method, a conventionally known method is applied. for example.
フタロシアニンを上記の無機酸に溶解し、その後、水等
に溶液を注入する方法（アシッドペースティング法）、
フタロシアニンの無機酸塩スラリーとし、水等に注入す
る方法（アシッドスラリー法）、あるいはフタロシアニ
ンの無機酸塩をアンモニアガス等の塩基性物質によって
塩を分解し、フタロシアニンを析出させる方法等がある
。A method of dissolving phthalocyanine in the above inorganic acid and then injecting the solution into water etc. (acid pasting method),
There is a method in which a slurry of an inorganic acid salt of phthalocyanine is made and injected into water etc. (acid slurry method), or a method in which the inorganic acid salt of phthalocyanine is decomposed with a basic substance such as ammonia gas to precipitate phthalocyanine.
以上のようにして得られた電荷発生材料を。The charge generating material obtained as described above.
導電性支持体上に、または電荷輸送層上に、結着剤樹脂
と共に被覆手段により電荷発生層を形成する。溶剤と共
に被覆手段により電荷発生層を形成する。あるいは蒸着
法、スパッタリング法等により電荷発生層を形成するこ
とができる。なお、後２者の方法では保護層をさらに設
ける方法以外は、導電性支持体／電荷発生層／電荷輸送
層の積層順が好ましい。A charge generation layer is formed on the conductive support or on the charge transport layer together with a binder resin by a coating means. A charge generation layer is formed by coating means together with a solvent. Alternatively, the charge generation layer can be formed by a vapor deposition method, a sputtering method, or the like. In addition, in the latter two methods, except for the method in which a protective layer is further provided, the lamination order of conductive support/charge generation layer/charge transport layer is preferable.
電荷発生層を結着剤樹脂と共に形成する場合。When the charge generation layer is formed together with a binder resin.
結着剤樹脂、溶剤等と共に、ボールミル、アトライター
等の混線分散機で均一に分散させ、導電性支持体上に塗
布して、電荷発生層を形成する。A charge generating layer is formed by uniformly dispersing the mixture together with a binder resin, a solvent, etc. using a crosstalk dispersion machine such as a ball mill or an attritor, and coating it on a conductive support.
結着剤樹脂としてはメラミン樹脂、エポキシ樹脂、ケイ
素樹脂、ポリウレタン樹脂、ポリエステル樹脂、アルキ
ッド樹脂、アクリル樹脂。Binder resins include melamine resin, epoxy resin, silicone resin, polyurethane resin, polyester resin, alkyd resin, and acrylic resin.
キシレン樹脂、塩化ビニル−酢酸ビニル共重合体樹脂、
ポリカーボネート樹脂、繊維素誘導体などの体積固有抵
抗が１０００以上の絶縁性を有する結着剤樹脂、あるい
はポリビニルカルバゾール等の結着剤樹脂である。xylene resin, vinyl chloride-vinyl acetate copolymer resin,
A binder resin having an insulating property with a volume resistivity of 1000 or more, such as a polycarbonate resin or a cellulose derivative, or a binder resin such as polyvinyl carbazole.
この電荷発生材料、結着剤樹脂等を含む組成物を電子写
真感光体に通常用いられるアルミニウム板、導電処理し
た紙、プラスチックフィルムなどの導電性支持体上に塗
布し、感光層を形成する。塗布方法としては、必要なら
ば組成物に溶剤を加えて粘度を開塾し、エアードクター
コーター、ブレードコーター、ロントコ−ター、リバー
スロールコータ−、スプレーコーター。A composition containing this charge-generating material, a binder resin, etc. is coated on a conductive support such as an aluminum plate, conductivity-treated paper, or plastic film, which is commonly used in electrophotographic photoreceptors, to form a photosensitive layer. As for the coating method, if necessary, a solvent is added to the composition to increase the viscosity, and an air doctor coater, a blade coater, a rotary coater, a reverse roll coater, or a spray coater can be used.
ホントコーター、スクイーズコーター、グラビアコータ
ー等の塗布方式で被膜形成を行う。塗布後、必要に応じ
て適当な乾燥を行う。Film formation is performed using a coating method such as a Honto coater, squeeze coater, or gravure coater. After coating, perform appropriate drying if necessary.
また本発明による電荷発生層は、樹脂／電荷発生材料が
重量比で１以上であり１例えば、酸化亜鉛を用いた感光
体の場合に比べ樹脂量が多く、被膜の物理的強度があり
、可撓性に富む。In addition, the charge generation layer according to the present invention has a resin/charge generation material weight ratio of 1 or more, 1For example, the amount of resin is larger than in the case of a photoreceptor using zinc oxide, and the film has physical strength and is flexible. Highly flexible.
また導電性支持体との接着力が大きい、耐湿性が良好で
ある。経時変化が少ない、毒性上の問題がない、製造が
容易であり安価である等の実用上優れた特徴を持つ。It also has a high adhesive strength with the conductive support and good moisture resistance. It has excellent practical characteristics such as little change over time, no toxicity problems, easy production, and low cost.
電荷発生層の厚さは、０．０１−１０μ清程度であり、
蒸着法、スパッタリング法以外では。The thickness of the charge generation layer is about 0.01-10 μm thick,
Other than vapor deposition and sputtering methods.
０．５〜１０μｍ程度であり、Ｘ蒸着法等では０゜Ｏ１
〜２μ謡程度である。It is about 0.5 to 10 μm, and 0°O1 in the X evaporation method etc.
It is about 2μ songs.
電荷発生層上に積層する電荷輸送層は、電荷発生層で発
生した電荷を感光体表面まで移動させる層であり、電荷
発生層の感光領域の光に対して透明であることが望まし
く、電荷輸送材料単独またはこれを樹脂中に分散、溶解
させた形で電荷発生層の上または導電性支持体上に形成
される。単独電荷輸送材料としてはポリビニルカルバゾ
ールおよびその誘導体、あるいはセレン蒸着膜等も使用
できる。一方樹脂中に分散。The charge transport layer laminated on the charge generation layer is a layer that transports the charges generated in the charge generation layer to the surface of the photoreceptor, and is preferably transparent to light from the photosensitive area of the charge generation layer. The material is formed alone or in the form of a dispersed or dissolved material in a resin on the charge generation layer or on the conductive support. As the sole charge transporting material, polyvinylcarbazole and its derivatives, or a selenium vapor-deposited film can also be used. On the other hand, it is dispersed in the resin.
溶解させる場合には、樹脂としてポリカーボネート、ポ
リエステル等を使用でき、このときの樹脂に対する電荷
輸送材料の重量比は０．１〜０゜８望ましくは０．３〜
０．６とすることが適当である。また、電荷輸送層の厚
さは特に限定されないが１通常５〜５０μ驕とすること
が適当である。In the case of dissolving, polycarbonate, polyester, etc. can be used as the resin, and the weight ratio of the charge transport material to the resin at this time is 0.1 to 0.8, preferably 0.3 to 0.8.
It is appropriate to set it to 0.6. Further, the thickness of the charge transport layer is not particularly limited, but it is usually appropriate to set it to 5 to 50 .mu.m thick.
本発明における電荷輸送材料としては１例えばカルバゾ
ール、Ｎ−エチルカルバゾール、Ｎ−ビニルカルバゾー
ル、Ｎ−イソプロピルカルバゾール、Ｎ−フェニルカル
バゾール、テトラセン、クリセン、ピレン、ペリレン、
２−フェニルナフタレン、アザピレン、２．３−ベンゾ
クリセン、３．４−ベンゾピレン、フルオレン、１゜２
−ベンゾフルオレン、２．３−ベンゾフルオレン、４−
（２−フルオレニルアゾ）レゾルシノール、４− （２
−フルオレニルアゾ）ｍ−クレゾール、２−Ｐ−アニソ
ールアミノフルオレン、Ｐ−ジエチルアミノ−アゾベン
ゼン、１−（２−チアゾリルアゾ）−２−ナフトール、
４−アニソ−ルア定ノアゾベンゼン、カシオン、Ｎ。Examples of charge transport materials in the present invention include carbazole, N-ethylcarbazole, N-vinylcarbazole, N-isopropylcarbazole, N-phenylcarbazole, tetracene, chrysene, pyrene, perylene,
2-phenylnaphthalene, azapyrene, 2.3-benzochrysene, 3.4-benzopyrene, fluorene, 1゜2
-benzofluorene, 2,3-benzofluorene, 4-
(2-fluorenylazo)resorcinol, 4-(2
-fluorenylazo)m-cresol, 2-P-anisoleaminofluorene, P-diethylamino-azobenzene, 1-(2-thiazolyl azo)-2-naphthol,
4-anisole azobenzene, cation, N.
Ｎ−ジメチル−Ｐ−フェニルアゾアニリン、Ｐ−（ジメ
チルアミノ）スチルベン、１．４−ビス（２−メチルス
チリル）ベンゼン、９− （４−ジエチルアミノスチリ
ル）アントラセン、２．５−ビス（４−ジエチルアミノ
フェノール）−１゜３．５−オキサジアゾール、■−フ
ェニルー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−フェニ
ル−３−メチル−５−ピラゾロンおよび２− （ｍ−ナ
フチル）−３−フェニルオキサゾール、Ｐ−ジエチルア
ミノベンズアルデヒド−（ジフェニルヒドラゾン）等を
挙げることができる。N-dimethyl-P-phenylazoaniline, P-(dimethylamino)stilbene, 1,4-bis(2-methylstyryl)benzene, 9-(4-diethylaminostyryl)anthracene, 2,5-bis(4-diethylamino) phenol)-1゜3.5-oxadiazole, ■-phenyl-3-(P-diethylaminostyryl)-5-(
P-diethylaminophenyl>pyrazoline, 1-phenyl-3-methyl-5-pyrazolone, 2-(m-naphthyl)-3-phenyloxazole, P-diethylaminobenzaldehyde (diphenylhydrazone), and the like.
また、樹脂（結着剤）としては、ポリ塩化ビニル、塩化
ビニル−酢酸ビニル共重合体、ポリカーボネート、ポリ
スチレン、スチレン−ブタジェン共重合体、ポリエステ
ル、ポリビニルカルバゾール、ポリウレタン、エポキシ
樹脂、フェノキシ樹脂、ポリアミド、アクリル樹脂およ
びシリコーン樹脂等を挙げることができる。In addition, as the resin (binder), polyvinyl chloride, vinyl chloride-vinyl acetate copolymer, polycarbonate, polystyrene, styrene-butadiene copolymer, polyester, polyvinylcarbazole, polyurethane, epoxy resin, phenoxy resin, polyamide, Examples include acrylic resins and silicone resins.
本発明において、電荷発生層およびまたは電荷輸送層に
、必要に応じて、増感剤、その他の添加剤を加えること
ができる。In the present invention, a sensitizer and other additives can be added to the charge generation layer and/or the charge transport layer, if necessary.
本発明の電子写真感光体は印刷版作製用の電子写真体と
しても使用することができる。The electrophotographic photoreceptor of the present invention can also be used as an electrophotographic material for producing printing plates.
本発明の電子写真感光体はインダクシロン効果が減少し
ていることにより階調性が良好となり、感度にも優れ、
さらに導電性支持体／電荷発生層／電荷輸送層の構成で
は特に帯電、Ｉｔ光などのプロセス繰り返しに伴う疲労
現象が改善されるという利点もある。The electrophotographic photoreceptor of the present invention has good gradation due to the reduced induxillon effect, and has excellent sensitivity.
Furthermore, the structure of conductive support/charge generation layer/charge transport layer has the advantage that fatigue phenomena associated with repeated processes such as charging and It light are improved.
以下、実施例および比較例により本発明を説明する。例
中ｒ部」とは重量部を示す。The present invention will be explained below with reference to Examples and Comparative Examples. In the examples, "r parts" indicates parts by weight.
実施例１
銅フタロシアニン４０部、モノニトロ銅フタロシアニン
１部を９８％濃硫＠５００部に十分攪拌しながら溶解す
る。溶解した液を水１０００部に十分攪拌しながら注入
し、銅フタロシアニン、モノニトロ鋼フタロシアニンｍ
成ｍを析出させた後１口過・水洗し、減圧下１２０℃で
乾燥した。Example 1 40 parts of copper phthalocyanine and 1 part of mononitro copper phthalocyanine are dissolved in 500 parts of 98% concentrated sulfur with thorough stirring. Pour the dissolved solution into 1000 parts of water with thorough stirring, and add copper phthalocyanine and mononitro steel phthalocyanine m.
After precipitating the component, it was filtered once, washed with water, and dried at 120° C. under reduced pressure.
この組成物１０部、アクリルポリオール（代用薬品工業
■製）３６部、エポキシ樹脂（シェル化学社製）５部お
よびメチルエチルケトン：セロソルブアセテート（１：
１）５０部からなる組成物をボールミルにより、２４時
間混練して、光導電性塗料を調整し、この塗料をアルミ
ニウム支持体上に約１μとなるように塗布し。10 parts of this composition, 36 parts of acrylic polyol (manufactured by Yayoi Yakuhin Kogyo ■), 5 parts of epoxy resin (manufactured by Shell Chemical Co., Ltd.), and methyl ethyl ketone: cellosolve acetate (1:
1) A photoconductive paint was prepared by kneading 50 parts of the composition in a ball mill for 24 hours, and this paint was coated on an aluminum support to a thickness of about 1 μm.
電荷発生層を形成した。A charge generation layer was formed.
次にポリカーボネート樹脂（奇人化成製）１０部、ポリ
エステル樹脂（グツドイヤー製）３部をテトラヒドロフ
ランおよびトルエン溶媒１００部で混合した。溶媒の重
量比は９：１である。次にｐ−ジエチルアミノベンズア
ルデヒド−（ジフェニルヒドラゾン）９部をシリコンオ
イル０．０２部と共に添加した。この液を電荷発生層の
上に約１５μとなるように塗布し、８０℃で乾燥して電
荷輸送層を形成し、積層感光体を得た。Next, 10 parts of polycarbonate resin (manufactured by Kijin Kasei) and 3 parts of polyester resin (manufactured by Gutdeyer) were mixed with tetrahydrofuran and 100 parts of toluene solvent. The weight ratio of solvents is 9:1. Next, 9 parts of p-diethylaminobenzaldehyde (diphenylhydrazone) were added together with 0.02 part of silicone oil. This liquid was applied onto the charge generation layer to a thickness of about 15μ and dried at 80° C. to form a charge transport layer to obtain a laminated photoreceptor.
実施例２
無金属フタロシアニン３０部、ジニトロ銅フタロシアニ
ン０．５部を９８％濃硫酸５００部に十分攪拌しながら
溶解する。溶解した液を水３０００部に注入しフタロシ
アニン系組成物を析出させた後２口過・水洗し、減圧下
１２０℃で乾燥する。この組成物５部と熱可塑性アクリ
ル樹脂０ＸＬ−９７（三井東圧製）２０重量部。Example 2 30 parts of metal-free phthalocyanine and 0.5 part of dinitrocopper phthalocyanine are dissolved in 500 parts of 98% concentrated sulfuric acid with thorough stirring. The dissolved solution was poured into 3000 parts of water to precipitate the phthalocyanine composition, which was then filtered twice, washed with water, and dried at 120° C. under reduced pressure. 5 parts of this composition and 20 parts by weight of thermoplastic acrylic resin 0XL-97 (manufactured by Mitsui Toatsu).
酢酸ブチル：セロソルブアセテ−） （１： １）３０
部からなる組成物をボールミルにより２４時間混練して
光導電性塗料を調整し、この塗料をアルミニウム支持体
上に約１μとなるように塗布し、電荷発生層を形成した
。Butyl acetate: cellosolve acetate) (1: 1) 30
A photoconductive coating material was prepared by kneading the composition consisting of the following parts in a ball mill for 24 hours, and this coating material was coated on an aluminum support to a thickness of about 1 .mu.m to form a charge generating layer.
次にポリカーボネート樹脂（奇人化成Ｍ）１０部、ポリ
エステル樹脂（グツドイヤー製） ５部、アクリル樹脂
（三菱化成製）５部をテトラヒドロフラン：トルエン（
９：１）１５０部で溶解させた。次にこの中に２．５−
ビス（４ジエチルアミノフエニル）１，３．４−オキサ
ジアゾール１２部をシリコンオイル０．０２部と共に添
加した。この液を電荷発生層上に約１５μとなるよう塗
布し、８０℃で乾燥し、電荷輸送層を形成し、積層型感
光体を得た。Next, 10 parts of polycarbonate resin (Kijin Kasei M), 5 parts of polyester resin (manufactured by Gutdeyer), and 5 parts of acrylic resin (manufactured by Mitsubishi Kasei) were mixed with tetrahydrofuran:toluene (
9:1) and 150 parts. Next, in this 2.5-
12 parts of bis(4-diethylaminophenyl) 1,3,4-oxadiazole were added along with 0.02 part of silicone oil. This liquid was coated on the charge generation layer to a thickness of about 15 μm and dried at 80° C. to form a charge transport layer to obtain a laminated photoreceptor.
実施例３
実施例２の電荷輸送層形成において、２．５−ビス（４
−ジエチルアミノフェニル）１，３．４−オキサジアゾ
ールのかわりに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）−
２−ピラゾリンを添加したこと以外は実施例２と全く同
様の一方法で感光体を作製した。Example 3 In forming the charge transport layer in Example 2, 2.5-bis(4
-diethylaminophenyl)1,3.4-oxadiazole instead of 1-phenyl-3-(p-diethylaminostyryl)-5-(p-diethylaminophenyl)-
A photoreceptor was produced in the same manner as in Example 2 except that 2-pyrazoline was added.
比較例１
β型鋼フタロシアニン１０部と熱硬化性アクリル樹脂３
２部、メラミン樹脂８部および酢酸ブチル：セロソルブ
アセテート（１：１）５０部からなる組成物をボールミ
ルにより２４時間混練して光導電性塗料を調整し、この
塗料をアルミニウム支持体上に約１μとなるように塗布
し、電荷発生層を形成した。Comparative Example 1 10 parts of β-type steel phthalocyanine and 3 parts of thermosetting acrylic resin
A photoconductive coating was prepared by kneading a composition consisting of 2 parts of melamine resin, 8 parts of melamine resin, and 50 parts of butyl acetate:cellosolve acetate (1:1) for 24 hours in a ball mill, and the coating was coated on an aluminum support with a coating of about 1 μm. A charge generation layer was formed.
次に、実施例１の電荷輸送層と同様にして。Next, in the same manner as the charge transport layer of Example 1.
電荷発生層の上に約１５μとなるよう塗布し。Coat it on the charge generation layer to a thickness of about 15μ.
８０℃で乾燥し、電荷輸送層を形成し、積層型感光体を
得た。It was dried at 80° C. to form a charge transport layer and obtain a laminated photoreceptor.
比較例２
比較例の処方の中からβ型鋼フタロシアニンを無金属フ
タロシアニンにかえた以外は比較例１と全く同様の方法
で感光体を作成した。Comparative Example 2 A photoreceptor was prepared in exactly the same manner as in Comparative Example 1, except that β-type steel phthalocyanine was replaced with metal-free phthalocyanine in the formulation of Comparative Example.
次に以上の感光体を市販のカールソン方式電子写真複写
機を用いて−６，５Ｋ Ｖのコロナ帯電を０．２秒間行
った時の表面電位（Ｖ）および各Ｖが１／２になるに要
する露光量（Ｅｌ／２）を測定し９次表の結果を得た。Next, the above photoconductor was corona charged at -6.5 KV for 0.2 seconds using a commercially available Carlson type electrophotographic copying machine, and the surface potential (V) and each V became 1/2. The required exposure amount (El/2) was measured and the results shown in the 9th table were obtained.
以上の結果かられかるように、極めて高感度であり、又
、フタロシアニン顔料の特徴である長波長域の感度を保
持し１本発明の電子写真感光体は、一般の複写機や半導
体レーザー（λ＝７５０〜８５０μｍ）を光源とするプ
リンター等にも使用出来る優れた感光体である。As can be seen from the above results, the electrophotographic photoreceptor of the present invention has extremely high sensitivity and maintains the sensitivity in the long wavelength range, which is a characteristic of phthalocyanine pigments. It is an excellent photoreceptor that can also be used in printers that use a light source of 750 to 850 μm).
特許出願人
東洋インキ製造株式会社
手続補正書（自発）
昭和５８年 ９月２７ 日
特許庁長官殿
■、事件の表示 昭和５８年特許Ｈ第１５７９１２号２
、発明の名称 電子写真感光体
３、補正をする者
事件との関係 特許出願人
明細書の「発明の詳細な説明」の欄
６、補正の内容Patent Applicant Toyo Ink Mfg. Co., Ltd. Procedural Amendment (Spontaneous) September 27, 1980 To the Commissioner of the Japan Patent Office■, Indication of the Case 1988 Patent H No. 157912 2
, Title of the invention Electrophotographic photoreceptor 3, Relationship with the case of the person making the amendment Column 6 of "Detailed description of the invention" in the patent applicant's specification, Contents of the amendment
Claims (1)
ル基から選ばれる少なくとも１４１の電子吸引性基によ
って置換されたフタロシアニン誘導体を、フタロシアニ
ンと塩を形成し得る無機酸と混合した後、水もしくは塩
基性物質によって析出せしめて得られた電荷発生材料を
含む層、および電荷輸送層を形成してなることを特徴と
する電子写真感光体。[Claims] 1. Phthalocyanine and phthalocyanine on a conductive support. The benzene nucleus of the phthalocyanine molecule is a nitro group. A phthalocyanine derivative substituted with at least 141 electron-withdrawing groups selected from a cyano group, a halogen atom, a sulfone group, and a carboxyl group is mixed with an inorganic acid that can form a salt with the phthalocyanine, and then precipitated with water or a basic substance. An electrophotographic photoreceptor comprising a layer containing the obtained charge generating material and a charge transport layer.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58157912A JPS6050539A (en) | 1983-08-31 | 1983-08-31 | Electrophotographic sensitive body |
| CA000461573A CA1252331A (en) | 1983-08-31 | 1984-08-22 | Electrophotographic plates |
| GB08421718A GB2145835B (en) | 1983-08-31 | 1984-08-28 | Electrophotographic plates |
| FR8413345A FR2551561B1 (en) | 1983-08-31 | 1984-08-29 | ELECTROPHOTOGRAPHIC PHOTOGRAPHS |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58157912A JPS6050539A (en) | 1983-08-31 | 1983-08-31 | Electrophotographic sensitive body |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6050539A true JPS6050539A (en) | 1985-03-20 |
| JPH0358507B2 JPH0358507B2 (en) | 1991-09-05 |
Family
ID=15660164
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58157912A Granted JPS6050539A (en) | 1983-08-31 | 1983-08-31 | Electrophotographic sensitive body |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS6050539A (en) |
| CA (1) | CA1252331A (en) |
| FR (1) | FR2551561B1 (en) |
| GB (1) | GB2145835B (en) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3850697T2 (en) * | 1987-04-22 | 1994-12-15 | Hitachi Chemical Co Ltd | Electrophotographic plate. |
| US5200286A (en) * | 1987-06-04 | 1993-04-06 | Fuji Xerox Co., Ltd. | Electrophotographic photoreceptor |
| JPH01169454A (en) * | 1987-12-25 | 1989-07-04 | Koichi Kinoshita | Photosensitive body for digital light input |
| EP0348889B1 (en) * | 1988-06-27 | 1995-12-13 | Mitsubishi Chemical Corporation | Photoconductive material and process for producing the same |
| US5112711A (en) * | 1990-06-05 | 1992-05-12 | Eastman Kodak Company | Electrophotographic recording elements containing a combination of titanyl phthalocyanine-type pigments |
| US5283146A (en) * | 1991-07-22 | 1994-02-01 | Mitsubishi Petrochemical Co., Ltd. | Photoconductive phthalocyanine composition |
| JP3119717B2 (en) * | 1992-05-11 | 2000-12-25 | 三菱化学株式会社 | Electrophotographic photoreceptor |
| WO1993024865A1 (en) * | 1992-06-04 | 1993-12-09 | Agfa-Gevaert Naamloze Vennootschap | Electrophotographic material containing particular phthalocyanines |
| EP0573084B1 (en) * | 1992-06-04 | 1997-04-09 | Agfa-Gevaert N.V. | Electrophotographic recording material containing phthalocyanines |
| ES2092427B1 (en) * | 1993-05-04 | 1997-10-16 | Univ Pais Vasco | PROCEDURE FOR OBTAINING AN ANTI-STATIC POLYMER BASED ON POLY (N-VINYL CARBAZOLE) |
| US5595846A (en) * | 1994-06-22 | 1997-01-21 | Mitsubishi Chemical Corporation | Phthalocyanine mixed crystal, production method thereof,and electrophotographic photoreceptor |
| JP4116109B2 (en) * | 1997-02-19 | 2008-07-09 | 大日本印刷株式会社 | Composition for electroluminescence device |
| US6720039B1 (en) | 1997-02-19 | 2004-04-13 | Dai Nippon Printing Co., Ltd. | Liquid crystalline compounds and process for producing the same |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58166355A (en) * | 1982-03-29 | 1983-10-01 | Toyo Ink Mfg Co Ltd | Electrophotographic receptor |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1127323B (en) * | 1953-08-29 | 1962-04-12 | Basf Ag | Solvent-stable mixture of copper phthalocyanine pigment dyes of the ª‡ form |
| JPS494338B1 (en) * | 1964-06-15 | 1974-01-31 | ||
| US3956524A (en) * | 1974-12-04 | 1976-05-11 | Xerox Corporation | Method for the preparation of electrostatographic photoreceptors |
| CA1095309A (en) * | 1975-09-22 | 1981-02-10 | Philip O. Sliva | Photosensitive device with organic topcoat containing 2,4,7-trinitro-9-fluorenone dispersed in poly (vinylcarbazole) |
-
1983
- 1983-08-31 JP JP58157912A patent/JPS6050539A/en active Granted
-
1984
- 1984-08-22 CA CA000461573A patent/CA1252331A/en not_active Expired
- 1984-08-28 GB GB08421718A patent/GB2145835B/en not_active Expired
- 1984-08-29 FR FR8413345A patent/FR2551561B1/en not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58166355A (en) * | 1982-03-29 | 1983-10-01 | Toyo Ink Mfg Co Ltd | Electrophotographic receptor |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0358507B2 (en) | 1991-09-05 |
| FR2551561B1 (en) | 1988-09-16 |
| GB2145835A (en) | 1985-04-03 |
| GB8421718D0 (en) | 1984-10-03 |
| CA1252331A (en) | 1989-04-11 |
| GB2145835B (en) | 1986-08-28 |
| FR2551561A1 (en) | 1985-03-08 |
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