JPH04212165A - Electrophotographic sensitive body - Google Patents
Electrophotographic sensitive bodyInfo
- Publication number
- JPH04212165A JPH04212165A JP3373391A JP3373391A JPH04212165A JP H04212165 A JPH04212165 A JP H04212165A JP 3373391 A JP3373391 A JP 3373391A JP 3373391 A JP3373391 A JP 3373391A JP H04212165 A JPH04212165 A JP H04212165A
- Authority
- JP
- Japan
- Prior art keywords
- group
- substituted
- parts
- unsubstituted
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 51
- 108091008695 photoreceptors Proteins 0.000 claims description 59
- 150000001875 compounds Chemical class 0.000 claims description 34
- -1 9-anthryl group Chemical group 0.000 claims description 31
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 27
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 125000000732 arylene group Chemical group 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 abstract description 7
- 230000006866 deterioration Effects 0.000 abstract description 3
- 230000035945 sensitivity Effects 0.000 abstract description 3
- MNCMBBIFTVWHIP-UHFFFAOYSA-N 1-anthracen-9-yl-2,2,2-trifluoroethanone Chemical group C1=CC=C2C(C(=O)C(F)(F)F)=C(C=CC=C3)C3=CC2=C1 MNCMBBIFTVWHIP-UHFFFAOYSA-N 0.000 abstract 2
- 238000007786 electrostatic charging Methods 0.000 abstract 1
- 238000010030 laminating Methods 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 174
- 238000000576 coating method Methods 0.000 description 95
- 239000000126 substance Substances 0.000 description 94
- 239000011248 coating agent Substances 0.000 description 92
- 239000007788 liquid Substances 0.000 description 67
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 36
- 229920005989 resin Polymers 0.000 description 36
- 239000011347 resin Substances 0.000 description 36
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 26
- 239000000243 solution Substances 0.000 description 26
- 239000011241 protective layer Substances 0.000 description 24
- 125000005843 halogen group Chemical group 0.000 description 19
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 19
- 125000003545 alkoxy group Chemical group 0.000 description 17
- 239000000203 mixture Substances 0.000 description 17
- 239000004417 polycarbonate Substances 0.000 description 17
- 229920000515 polycarbonate Polymers 0.000 description 17
- 125000001424 substituent group Chemical group 0.000 description 16
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 125000000623 heterocyclic group Chemical group 0.000 description 15
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 14
- 150000002430 hydrocarbons Chemical group 0.000 description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 11
- 239000011230 binding agent Substances 0.000 description 11
- 229920000728 polyester Polymers 0.000 description 10
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 8
- 239000004419 Panlite Substances 0.000 description 8
- 125000003282 alkyl amino group Chemical group 0.000 description 8
- 229910052782 aluminium Inorganic materials 0.000 description 8
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 125000001624 naphthyl group Chemical group 0.000 description 7
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 6
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 6
- 229920002451 polyvinyl alcohol Polymers 0.000 description 6
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 6
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 6
- 229910052721 tungsten Inorganic materials 0.000 description 6
- 239000010937 tungsten Substances 0.000 description 6
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229920000139 polyethylene terephthalate Polymers 0.000 description 5
- 239000005020 polyethylene terephthalate Substances 0.000 description 5
- 125000005504 styryl group Chemical group 0.000 description 5
- 229910001887 tin oxide Inorganic materials 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 239000004372 Polyvinyl alcohol Substances 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 125000001246 bromo group Chemical group Br* 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229910052759 nickel Inorganic materials 0.000 description 4
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000004408 titanium dioxide Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 229920000178 Acrylic resin Polymers 0.000 description 3
- 239000004925 Acrylic resin Substances 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 125000004663 dialkyl amino group Chemical group 0.000 description 3
- 239000003822 epoxy resin Substances 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 125000001041 indolyl group Chemical group 0.000 description 3
- 229910010272 inorganic material Inorganic materials 0.000 description 3
- 239000011147 inorganic material Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 239000004014 plasticizer Substances 0.000 description 3
- 229920002492 poly(sulfone) Polymers 0.000 description 3
- 229920001230 polyarylate Polymers 0.000 description 3
- 229920000647 polyepoxide Polymers 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 229920002050 silicone resin Polymers 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- VHQGURIJMFPBKS-UHFFFAOYSA-N 2,4,7-trinitrofluoren-9-one Chemical compound [O-][N+](=O)C1=CC([N+]([O-])=O)=C2C3=CC=C([N+](=O)[O-])C=C3C(=O)C2=C1 VHQGURIJMFPBKS-UHFFFAOYSA-N 0.000 description 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 2
- 229920004313 LEXAN™ RESIN 141 Polymers 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 239000000783 alginic acid Substances 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical group C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 125000005577 anthracene group Chemical group 0.000 description 2
- 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 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 239000007822 coupling agent Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 125000004986 diarylamino group Chemical group 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229910000856 hastalloy Inorganic materials 0.000 description 2
- 230000001678 irradiating effect Effects 0.000 description 2
- 230000031700 light absorption Effects 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000005011 phenolic resin Substances 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
- 229920002647 polyamide Polymers 0.000 description 2
- 229920006122 polyamide resin Polymers 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 239000004800 polyvinyl chloride Substances 0.000 description 2
- 229920000915 polyvinyl chloride Polymers 0.000 description 2
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 2
- 229920002545 silicone oil Polymers 0.000 description 2
- 238000004544 sputter deposition Methods 0.000 description 2
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 1
- WQGWMEKAPOBYFV-UHFFFAOYSA-N 1,5,7-trinitrothioxanthen-9-one Chemical compound C1=CC([N+]([O-])=O)=C2C(=O)C3=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C3SC2=C1 WQGWMEKAPOBYFV-UHFFFAOYSA-N 0.000 description 1
- JOERSAVCLPYNIZ-UHFFFAOYSA-N 2,4,5,7-tetranitrofluoren-9-one Chemical compound O=C1C2=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C2C2=C1C=C([N+](=O)[O-])C=C2[N+]([O-])=O JOERSAVCLPYNIZ-UHFFFAOYSA-N 0.000 description 1
- FVNMKGQIOLSWHJ-UHFFFAOYSA-N 2,4,5,7-tetranitroxanthen-9-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)C3=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C3OC2=C1[N+]([O-])=O FVNMKGQIOLSWHJ-UHFFFAOYSA-N 0.000 description 1
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
- QPKNFEVLZVJGBM-UHFFFAOYSA-N 2-aminonaphthalen-1-ol Chemical class C1=CC=CC2=C(O)C(N)=CC=C21 QPKNFEVLZVJGBM-UHFFFAOYSA-N 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- JNGDCMHTNXRQQD-UHFFFAOYSA-N 3,6-dioxocyclohexa-1,4-diene-1,2,4,5-tetracarbonitrile Chemical compound O=C1C(C#N)=C(C#N)C(=O)C(C#N)=C1C#N JNGDCMHTNXRQQD-UHFFFAOYSA-N 0.000 description 1
- PYSRRFNXTXNWCD-UHFFFAOYSA-N 3-(2-phenylethenyl)furan-2,5-dione Chemical compound O=C1OC(=O)C(C=CC=2C=CC=CC=2)=C1 PYSRRFNXTXNWCD-UHFFFAOYSA-N 0.000 description 1
- 229910000838 Al alloy Inorganic materials 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 229930182556 Polyacetal Natural products 0.000 description 1
- 239000004962 Polyamide-imide Substances 0.000 description 1
- 239000004695 Polyether sulfone Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229920000147 Styrene maleic anhydride Polymers 0.000 description 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 229920002433 Vinyl chloride-vinyl acetate copolymer Polymers 0.000 description 1
- FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000001691 aryl alkyl amino group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Chemical group 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 229910052798 chalcogen Inorganic materials 0.000 description 1
- 150000001787 chalcogens Chemical class 0.000 description 1
- 239000000460 chlorine Chemical group 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000004965 chloroalkyl group Chemical group 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 239000002482 conductive additive Substances 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 229910052593 corundum Inorganic materials 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- NJLLQSBAHIKGKF-UHFFFAOYSA-N dipotassium dioxido(oxo)titanium Chemical compound [K+].[K+].[O-][Ti]([O-])=O NJLLQSBAHIKGKF-UHFFFAOYSA-N 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 125000004970 halomethyl group Chemical group 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 229910001120 nichrome Inorganic materials 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 229920006287 phenoxy resin Polymers 0.000 description 1
- 239000013034 phenoxy resin Substances 0.000 description 1
- 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
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 229920003216 poly(methylphenylsiloxane) Polymers 0.000 description 1
- 229920002285 poly(styrene-co-acrylonitrile) Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002312 polyamide-imide Polymers 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920001470 polyketone Polymers 0.000 description 1
- 229920000306 polymethylpentene Polymers 0.000 description 1
- 239000011116 polymethylpentene Substances 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920006380 polyphenylene oxide Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920006215 polyvinyl ketone Polymers 0.000 description 1
- 229920002102 polyvinyl toluene Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Inorganic materials [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- NLDYACGHTUPAQU-UHFFFAOYSA-N tetracyanoethylene Chemical group N#CC(C#N)=C(C#N)C#N NLDYACGHTUPAQU-UHFFFAOYSA-N 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000005309 thioalkoxy group Chemical group 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 229910001845 yogo sapphire Inorganic materials 0.000 description 1
Landscapes
- Photoreceptors In Electrophotography (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
Description
【０００１】0001
【産業上の利用分野】本発明は電子写真用感光体の改良
に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to improvements in electrophotographic photoreceptors.
【０００２】0002
【従来の技術】近年、電子写真複写機に使用される感光
体として、低価格、生産性及び無公害等の利点を有する
有機系の感光材料を用いたものが普及しはじめている。2. Description of the Related Art In recent years, organic photosensitive materials, which have advantages such as low cost, productivity, and non-pollution, have become popular as photoreceptors used in electrophotographic copying machines.
【０００３】有機系の電子写真感光体には、ポリビニル
カルバゾール（ＰＶＫ）に代表される光導電性樹脂、Ｐ
ＶＫ−ＴＮＦ（２，４，７−トリニトロフルオレノン）
に代表される電荷移動錯体型、フタロシアニン−バイン
ダーに代表される顔料分散型、電荷発生物質と電荷輸送
物質とを組合せて用いる機能分離型の感光体などが知ら
れており、特に機能分離型の感光体が注目されている。Organic electrophotographic photoreceptors include photoconductive resins such as polyvinylcarbazole (PVK), P
VK-TNF (2,4,7-trinitrofluorenone)
Photoreceptors of the charge transfer complex type represented by , pigment dispersion type represented by phthalocyanine binder, and functionally separated type photoreceptors using a combination of a charge generating substance and a charge transporting substance are known. Photoreceptors are attracting attention.
【０００４】この様な機能分離型の高感度感光体を、カ
ールソンプロセスに適用した場合、帯電性が低く、電荷
保持特性が悪い（暗減衰が大きい）上、繰返し使用によ
る、これら特性の劣化が大きく、画像上に、濃度ムラ、
カブリ、また反転現像の場合、地汚れを生じるという欠
点を有している。When such a functionally separated high-sensitivity photoreceptor is applied to the Carlson process, it has low chargeability and poor charge retention properties (large dark decay), and these properties tend to deteriorate with repeated use. Large, uneven density on the image,
It has the drawbacks of fogging and, in the case of reversal development, background smearing.
【０００５】また一般に、高感度感光体は、前露光疲労
によって帯電性が低下する。この前露光疲労は主に電荷
生材料が吸収する光によって起こることから、光吸収に
よって発生した電荷が移動可能な状態で感光体内に残留
している時間が長い程、またその電荷の数が多い程、前
露光疲労による帯電性の低下が著しくなると考えられる
。即ち、光吸収によって発生した電荷が残留している状
態で帯電操作をしても、残留しているキャリアの移動で
表面電荷が中和される為、残留電荷が消費されるまで表
面電位は上昇しない、従って、前露光疲労分だけ表面電
位の上昇が遅れることになり、見かけ上の帯電位は低く
なる。[0005] Generally, high-sensitivity photoreceptors have reduced chargeability due to pre-exposure fatigue. This pre-exposure fatigue is mainly caused by light absorbed by charge-generating materials, so the longer the charges generated by light absorption remain in the photoconductor in a mobile state, the greater the number of charges. It is thought that the lower the chargeability becomes, the more the chargeability decreases due to pre-exposure fatigue. In other words, even if a charging operation is performed while the charge generated by light absorption remains, the surface charge will be neutralized by the movement of the remaining carriers, so the surface potential will increase until the residual charge is consumed. Therefore, the rise in surface potential is delayed by the amount of pre-exposure fatigue, and the apparent charged potential is lowered.
【０００６】上述の欠点に対して、例えば、特開昭４７
−６３４１、４８−３５４４および４８−１２０３４号
には硝酸セルロース系樹脂中間層が、特開昭４８−４７
３４４、５２−２５６３８、５８−３０７５７、５８−
６３９４５、５８−９５３５１、５８−９８７３９およ
び６０−６６２５８号にはナイロン系樹脂中間層が、特
開昭４９−６９３３２および５２−１０１３８号にはマ
レイン酸系樹脂中間層が、そして特開昭５８−１０５１
５５号にはポリビニルアルコール樹脂中間層がそれぞれ
開示されている。また、中間層の電気抵抗を制御すべく
種々の導電性添加物を樹脂中に含有させた中間層が提案
されている。例えば、特開昭５１−６５９４２号にはカ
ーボンまたはカルコゲン系物質を硬化性樹脂に分散した
中間層が、特開昭５２−８２２３８号には四級アンモニ
ウム塩を添加してイソシアネート系硬化剤を用いた熱重
合体中間層が、特開昭５５−１１８０４５１号には抵抗
調節剤を添加した樹脂中間層が、特開昭５８−５８５５
６号にはアルミニウムまたはスズの酸化物を分散した樹
脂中間層が、特開昭５８−９３０６２号には有機金属化
合物を添加した樹脂中間層が、特開昭５８−９３０６３
、６０−９７３６３および６０−１１１２５５号には導
電性粒子を分散した樹脂中間層が、さらに特開昭５９−
８４２５７、５９−９３４５３および６０−３２０５４
号にはＴｉＯ２とＳｎＯ２粉体とを分散した樹脂中間層
が開示されている。[0006] For the above-mentioned drawbacks, for example,
-6341, 48-3544 and 48-12034 have a cellulose nitrate resin intermediate layer, JP-A-48-47
344, 52-25638, 58-30757, 58-
Nos. 63945, 58-95351, 58-98739 and 60-66258 have nylon resin intermediate layers, JP-A-49-69332 and 52-10138 have maleic acid-based resin intermediate layers, and JP-A-58- 1051
No. 55 discloses a polyvinyl alcohol resin intermediate layer. In addition, intermediate layers have been proposed in which various conductive additives are contained in a resin in order to control the electrical resistance of the intermediate layer. For example, JP-A No. 51-65942 uses an intermediate layer in which carbon or chalcogen-based substances are dispersed in a curable resin, and JP-A No. 52-82238 uses an isocyanate-based curing agent with the addition of a quaternary ammonium salt. JP-A-55-1180451 discloses a thermopolymer intermediate layer with a resistance modifier added therein, while JP-A-58-5855 discloses a resin intermediate layer containing a resistance modifier.
No. 6 has a resin intermediate layer in which aluminum or tin oxide is dispersed, and JP-A-58-93062 has a resin intermediate layer to which an organometallic compound is added.
, No. 60-97363 and No. 60-111255 have a resin intermediate layer in which conductive particles are dispersed, and Japanese Patent Application Laid-Open No. 59-1989
84257, 59-93453 and 60-32054
No. 2, discloses a resin intermediate layer in which TiO2 and SnO2 powder are dispersed.
【０００７】しかしながら、繰り返し使用による帯電性
の低下、とりわけ帯電々位の立上りの遅れに関しては未
だに不充分であり、より一層の改善が望まれていた。ま
た、特開昭５４−８５２８号公報には、電子供与性物質
および／又は電子受容性物質で被服した電荷発生物質を
樹脂中に分散した層を有する感光体が、特開昭５４−３
４２４０号公報、特開昭６３−２８１１６７号公報には
、電荷発生層中に電荷輸送材を含有させた積層型感光体
が開示されているが、これらはいずれも上記諸要求を満
足するものではなかった。[0007] However, it is still insufficient in terms of the deterioration in charging properties due to repeated use, especially the delay in the rise of the charging potential, and further improvements have been desired. Furthermore, Japanese Patent Application Laid-Open No. 54-8528 discloses a photoreceptor having a layer in which a charge-generating substance coated with an electron-donating substance and/or an electron-accepting substance is dispersed in a resin.
No. 4240 and Japanese Patent Application Laid-open No. 63-281167 disclose laminated photoreceptors in which a charge transporting material is contained in a charge generation layer, but none of these satisfy the above requirements. There wasn't.
【０００８】[0008]
【発明が解決しようとする課題】本発明は、高感度であ
るとともに前露光疲労による帯電性の低下が著しく小さ
く、しかも帯電と露光の繰り返し後においても帯電電位
の立上りの遅れのない電子写真用感光体を提供すること
を目的とする。[Problems to be Solved by the Invention] The present invention provides a method for electrophotography that has high sensitivity, significantly reduces the deterioration in chargeability due to pre-exposure fatigue, and has no delay in the rise of the charging potential even after repeated charging and exposure. The purpose is to provide a photoreceptor.
【０００９】[0009]
【課題を解決するための手段】本発明によれば、導電性
支持体上に少なくとも電荷発生層と電荷輸送層を順次積
層してなる電子写真感光体において、該電荷発生層中に
下記化１（一般式（Ｉ））で示される化合物を含有して
なることを特徴とする電子写真感光体が提供される。[Means for Solving the Problems] According to the present invention, in an electrophotographic photoreceptor comprising at least a charge generation layer and a charge transport layer sequentially laminated on a conductive support, the charge generation layer contains the following compound: An electrophotographic photoreceptor containing a compound represented by the general formula (I) is provided.
【００１０】0010
【化１】
〔式中、Ａは９−アントリル基、置換又は無置換のＮ−
置換カルバゾリル基、Ｎ−置換フェノチアジニル基又は
−Ａｒ−Ｎ（Ｒ１）（Ｒ２）（式中Ａｒは置換又は無置
換のアリーレン基を表わし、Ｒ１及びＲ２は置換又は無
置換のアルキル基、置換又は無置換のアラルキル基、置
換又は無置換のアリール基を表わす）を表わし、Ｒは水
素原子、置換又は無置換のアルキル基、置換又は無置換
のアラルキル基又は置換又は無置換のアリール基を表わ
す。ｎは０〜８の整数を表わす。〕[Formula, A is a 9-anthryl group, substituted or unsubstituted N-
Substituted carbazolyl group, N-substituted phenothiazinyl group or -Ar-N(R1)(R2) (wherein Ar represents a substituted or unsubstituted arylene group, R1 and R2 are substituted or unsubstituted alkyl groups, substituted or R represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aryl group. n represents an integer from 0 to 8. ]
【００１１】また、本発明によれば、導電性支持体上に
少なくとも電荷発生層と電荷輸送層を順次積層中に下記
化２（一般式（ＩＩ））で示される化合物を含有してな
ることを特徴とする電子写真感光体が提供される。Further, according to the present invention, a compound represented by the following formula 2 (general formula (II)) is contained in the sequential lamination of at least a charge generation layer and a charge transport layer on a conductive support. An electrophotographic photoreceptor is provided.
【００１２】0012
【化２】
〔式中、Ａは９−アントリル基、置換又は無置換のＮ−
置換カルバゾリル基、Ｎ−置換フェノチアジニル基又は
−Ａｒ−Ｎ（Ｒ１）（Ｒ２）（式中Ａｒは置換又は無置
換のアリーレン基を表わし、Ｒ１及びＲ２は置換又は無
置換のアルキル基、置換又は無置換のアラルキル基、置
換又は無置換のアリール基を表わす）を表わし、Ｒは水
素原子、置換又は無置換のアルキル基、置換又は無置換
のアラルキル基又は置換又は無置換のアリル基を表わす
。ｍは２〜８の整数を表わす。ｎは０又は１の整数を表
わす。〕[In the formula, A is a 9-anthryl group, substituted or unsubstituted N-
Substituted carbazolyl group, N-substituted phenothiazinyl group or -Ar-N(R1)(R2) (wherein Ar represents a substituted or unsubstituted arylene group, R1 and R2 are substituted or unsubstituted alkyl groups, substituted or R represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted allyl group. m represents an integer from 2 to 8. n represents an integer of 0 or 1. ]
【００１３】上述したように、高感度の積層型有機電子
写真感光体は、くり返し使用によって、帯電の立上りの
遅れを生じ、その結果、帯電性の低下をまねくが、本発
明者らは、積層型有機電子写真感光体の電荷発生層に前
記一般式（Ｉ）又は（ＩＩ）で示される化合物を含有さ
せることによって、くり返し使用後の帯電々位の立上り
の遅れのない電子写真感光体が得られることを見い出し
、本発明を完成するに至た。[0013] As mentioned above, repeated use of a highly sensitive laminated organic electrophotographic photoreceptor causes a delay in the rise of charging, resulting in a decrease in charging property. By incorporating the compound represented by the general formula (I) or (II) into the charge generation layer of an electrophotographic organic electrophotographic photoreceptor, an electrophotographic photoreceptor that does not have a delay in the rise of the charge level after repeated use can be obtained. The present invention was completed based on this discovery.
【００１４】以下、図面に沿って、本発明を説明する。
図１は、本発明の電子写真感光体の構成例を示す断面図
であり、導電性支持体１１上に電荷発生層１５、次いで
電荷輸送層１７を設けた構成をとっている。The present invention will be explained below with reference to the drawings. FIG. 1 is a cross-sectional view showing an example of the structure of the electrophotographic photoreceptor of the present invention, in which a charge generation layer 15 and then a charge transport layer 17 are provided on a conductive support 11.
【００１５】図２は、本発明の別の構成例を示す断面図
であり、導電性支持体１１と電荷発生層１５の間に下引
層１３を設けたものである。FIG. 2 is a sectional view showing another example of the structure of the present invention, in which an undercoat layer 13 is provided between the conductive support 11 and the charge generation layer 15.
【００１６】図３と図４は、更に別の構成例を示す断面
図であり、図３は電荷輸送層１７の上に保護層１９を設
けたものであり、図４は下引層と保護層を同時に設けた
ものである。FIGS. 3 and 4 are cross-sectional views showing still another example of the structure. FIG. 3 shows a protective layer 19 provided on the charge transport layer 17, and FIG. 4 shows an undercoat layer and a protective layer 19. The layers are provided at the same time.
【００１７】導電性支持体１１としては、体積抵抗１０
１０Ωｃｍ下の導電性を示すもの、例えば、アルミニウ
ム、ニッケル、クロム、ニクロム、銅、銀、金、白金な
どの金属、酸化スズ、酸化インジウムなどの金属酸化物
を、蒸着又はスパッタリングにより、フィルム状もしく
は円筒状のプラスチック、紙等に被覆したもの、あるい
は、アルミニウム、アルミニウム合金、ニッケル、ステ
ンレス等の板およびそれらをＤ．Ｉ．，Ｉ．Ｉ．，押出
し、引抜き等の工法で素管化後、切削、超仕上げ、研摩
等で表面処理した管等を使用することができる。The conductive support 11 has a volume resistance of 10
Materials exhibiting conductivity of less than 10 Ωcm, such as metals such as aluminum, nickel, chromium, nichrome, copper, silver, gold, and platinum, and metal oxides such as tin oxide and indium oxide, are deposited in film form or by sputtering. Cylindrical plastic, paper, etc. coated, or plates made of aluminum, aluminum alloy, nickel, stainless steel, etc., and these are D. I. ,I. I. It is possible to use pipes that have been made into blank pipes by methods such as , extrusion, and drawing, and then surface-treated by cutting, superfinishing, polishing, etc.
【００１８】次に、電荷発生層１５について説明する。
電荷発生層１５は、電荷発生物質と前記一般式（Ｉ）又
は（ＩＩ）で示される化合物を主成分とする層で、必要
に応じてバインダー樹脂を用いることもある。Next, the charge generation layer 15 will be explained. The charge generation layer 15 is a layer mainly composed of a charge generation substance and a compound represented by the general formula (I) or (II), and may use a binder resin as necessary.
【００１９】バインダー樹脂としては、ポリアミド、ポ
リウレタン、ポリエステル、エポキシ樹脂、ポリケトン
、ポリカーボネート、シリコーン樹脂、アクリル樹脂、
ポリビニルブチラール、ポリビニルホルマール、ポリビ
ニルケトン、ポリスチレン、ポリ−Ｎ−ビニルカルバゾ
ール、ポリアクリルアミドなどが用いられる。Binder resins include polyamide, polyurethane, polyester, epoxy resin, polyketone, polycarbonate, silicone resin, acrylic resin,
Polyvinyl butyral, polyvinyl formal, polyvinyl ketone, polystyrene, poly-N-vinylcarbazole, polyacrylamide, etc. are used.
【００２０】一般式（Ｉ）で示される化合物としては次
の表１に示す化学構造式のものが好ましく用いられる。As the compound represented by the general formula (I), those having the chemical structural formula shown in Table 1 below are preferably used.
【００２１】[0021]
【表１−（１）】[Table 1-(1)]
【００２２】[0022]
【表１−（２）】[Table 1-(2)]
【００２３】[0023]
【表１−（３）】[Table 1-(3)]
【００２４】[0024]
【表１−（４）】[Table 1-(4)]
【００２５】[0025]
【表１−（５）】[Table 1-(5)]
【００２６】[0026]
【表１−（６）】[Table 1-(6)]
【００２７】[0027]
【表１−（７）】[Table 1-(7)]
【００２８】また、一般式（ＩＩ）で示される化合物と
しては次の表２に示す化学構造式のものが好ましく用い
られる。Further, as the compound represented by the general formula (II), those having the chemical structural formula shown in Table 2 below are preferably used.
【表２−（１）】[Table 2-(1)]
【００２９】[0029]
【表２−（２）】[Table 2-(2)]
【００３０】[0030]
【表２−（３）】[Table 2-(3)]
【００３１】[0031]
【表２−（４）】[Table 2-(4)]
【００３２】[0032]
【表２−（５）】[Table 2-(5)]
【００３３】[0033]
【表２−（６）】[Table 2-(6)]
【００３４】[0034]
【表２−（７）】[Table 2-(7)]
【００３５】[0035]
【表２−（８）】[Table 2-(8)]
【００３６】[0036]
【表２−（９）】[Table 2-(9)]
【００３７】[0037]
【表２−（１０）】[Table 2-(10)]
【００３８】[0038]
【表２−（１１）】[Table 2-(11)]
【００３９】[0039]
【表２−（１２）】[Table 2-(12)]
【００４０】[0040]
【表２−（１３）】[Table 2-(13)]
【００４１】[0041]
【表２−（１４）】[Table 2-(14)]
【００４２】[0042]
【表２−（１５）】[Table 2-(15)]
【００４３】[0043]
【表２−（１６）】[Table 2-(16)]
【００４４】電荷発生物質としては、公知の材料を用い
ることができるが、とりわけ以下の表３に示すジスアゾ
あるいはトリスアゾ顔料が好適に用いられる。As the charge generating substance, known materials can be used, but disazo or trisazo pigments shown in Table 3 below are particularly preferably used.
【表３−（１）】[Table 3-(1)]
【００４５】[0045]
【表３−（２）】[Table 3-(2)]
【００４６】[0046]
【表３−（３）】[Table 3-(3)]
【００４７】[0047]
【表３−（４）】[Table 3-(4)]
【００４８】[0048]
【表３−（５）】[Table 3-(5)]
【００４９】[0049]
【表３−（６）】[Table 3-(6)]
【００５０】これらのカップラー残基Ｃｐとしては、た
とえばフェノール類、ナフトール類などのフェノール性
水酸基を有する化合物、アミノ基を有する芳香族アミノ
化合物あるいはアミノ基とフェノール性水酸基を有する
アミノナフトール類、脂肪族もしくは芳香族のエノール
性ケトン基を有する化合物（活性メチレン基を有する化
合物）などが用いられ、好ましくは下記（一般式（１）
〜（１１）で表わされるものである。Examples of these coupler residues Cp include compounds having a phenolic hydroxyl group such as phenols and naphthols, aromatic amino compounds having an amino group, aminonaphthols having an amino group and a phenolic hydroxyl group, and aliphatic Alternatively, a compound having an aromatic enolic ketone group (a compound having an active methylene group) is used, preferably the following (general formula (1)
~(11).
【化３】
〔上記式（１），（２），（３）および（４）中、Ｘ，
Ｙ１，Ｚ，ｍおよびｎはそれぞれ以下のものを表 わ
す。
Ｘ：−ＯＨ、−Ｎ（Ｒ１）（Ｒ２）または−ＮＨＳＯ２
−Ｒ３ （Ｒ１およびＲ２は水素または置換もし
くは無置換のアルキル基を表わし、Ｒ３は置換もしくは
無置換のアルキル基または置換もしくは無置換のアリー
ル基を表わす。）Ｙ１：水素、ハロゲン、置換もしくは
無置換のアルキル基、置換もしくは無置換のアルコキシ
基、カルボキシ基、スルホン基、置換もしくは無置換の
スルファモイル基または−ＣＯＮ（Ｒ４）Ｙ２
（Ｒ４は水素、アルキル基またその置換体、フェニル基
またはその置換体を表わし、Ｙ２は炭化水素環基または
その置換体、複素環基またはその置換体、あるいは−Ｎ
＝Ｃ（Ｒ５）（Ｒ６）（但し、Ｒ５は炭化水素環基また
はその置換体、複素環基またはその置換体あるいはスチ
リル基またはその置換体、Ｒ６は水素、アルキル基、フ
ェニル基またはその置換体を表わすか、あるいはＲ５及
びＲ６はそれらに結合する炭素原子と共に環を形成して
もよい。）を示す。）
Ｚ ：炭化水素環またはその置換体あるいは複素環また
はその置換体
ｎ ：１または２の整数〕
ｍ ：１または２の整数[Formula (1), (2), (3) and (4), X,
Y1, Z, m and n each represent the following. X: -OH, -N(R1)(R2) or -NHSO2
-R3 (R1 and R2 represent hydrogen or a substituted or unsubstituted alkyl group, and R3 represents a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.) Y1: Hydrogen, halogen, substituted or unsubstituted an alkyl group, a substituted or unsubstituted alkoxy group, a carboxy group, a sulfone group, a substituted or unsubstituted sulfamoyl group, or -CON(R4)Y2
(R4 represents hydrogen, an alkyl group or a substituent thereof, a phenyl group or a substituent thereof, Y2 is a hydrocarbon ring group or a substituent thereof, a heterocyclic group or a substituent thereof, or -N
=C(R5)(R6) (However, R5 is a hydrocarbon ring group or a substituent thereof, a heterocyclic group or a substituent thereof, or a styryl group or a substituent thereof, R6 is hydrogen, an alkyl group, a phenyl group, or a substituent thereof or R5 and R6 may form a ring together with the carbon atoms bonded to them. ) Z: Hydrocarbon ring or its substituted product, or heterocycle or its substituted product n: An integer of 1 or 2] m: An integer of 1 or 2
【００５１】[0051]
【化４】
〔式（５）中、Ｒ７は置換もしくは無置換の炭化水素基
を表わし、Ｘは前記と同じである。〕embedded image [In formula (5), R7 represents a substituted or unsubstituted hydrocarbon group, and X is the same as above. ]
【００５２】[0052]
【化５】
〔式（６）中、Ａは芳香族炭化水素の２価基または窒素
原子を環内に含む複素環の２価基を表わす。（これらの
環は置換または無置換でもよい）。Ｘは前記と同じ。〕
embedded image [In formula (6), A represents a divalent group of an aromatic hydrocarbon or a divalent group of a heterocycle containing a nitrogen atom in the ring. (These rings may be substituted or unsubstituted). X is the same as above. ]
【００５３】[0053]
【化６】
〔式中、Ｒ８はアルキル基、カルバモイル基、カルボキ
シ基またはそのエステルを表わし、Ａｒ１は炭化水素環
基またはその置換体を表わし、Ｘは前記と同じである。
〕embedded image [In the formula, R8 represents an alkyl group, a carbamoyl group, a carboxy group, or an ester thereof, Ar1 represents a hydrocarbon ring group or a substituent thereof, and X is the same as above. ]
【００５４】[0054]
【化７】
〔上記式（８）および（９）中、Ｒ９は水素または置換
もしくは無置換の炭化水素基を表わし、Ａｒ２は炭化水
素環基またはその置換体を表わす。〕embedded image [In the above formulas (8) and (9), R9 represents hydrogen or a substituted or unsubstituted hydrocarbon group, and Ar2 represents a hydrocarbon ring group or a substituted product thereof. ]
【００５５】前記一般式（１），（２），（３）または
（４）のＺの炭化水素環としてはベンゼン環、ナフタレ
ン環などが例示でき、また複素環（置換を持っていても
よい）としてはインドール環、カルバゾール環、ベンゾ
ラン環、ジベンゾフラン環などが例示できる。Ｚの環に
おける置換基としては塩素原子、臭素原子などのハロゲ
ン原子が例示できる。Examples of the hydrocarbon ring Z in the general formula (1), (2), (3) or (4) include a benzene ring, a naphthalene ring, and a heterocyclic ring (which may have substitutions). ) can be exemplified by an indole ring, a carbazole ring, a benzolane ring, a dibenzofuran ring, etc. Examples of substituents on the ring of Z include halogen atoms such as chlorine atoms and bromine atoms.
【００５６】Ｙ２またはＲ５における炭化水素環基とし
ては、フェニル基、ナフチル基、アントリル基、ピレニ
ル基などが、また、複素環基としてはピリジル基、チェ
ニル基、フリル基、インドリル基、ベンゾフラニル基、
カルバゾリル基、ジベンゾフラニル基などが例示でき、
さらに、Ｒ５およびＲ６が結合して形成する環としては
、フルオレン環などが例示できる。Examples of the hydrocarbon ring group in Y2 or R5 include phenyl group, naphthyl group, anthryl group, pyrenyl group, etc., and examples of the heterocyclic group include pyridyl group, chenyl group, furyl group, indolyl group, benzofuranyl group,
Examples include carbazolyl group, dibenzofuranyl group, etc.
Furthermore, examples of the ring formed by combining R5 and R6 include a fluorene ring.
【００５７】Ｙ２またはＲ５の炭化水素環基または複素
環基あるいはＲ５およびＲ６によって形成される環にお
ける置換基としては、メチル基、エチル基、プロピル基
、ブチル基などのアルキル基、メトキシ基、エトキシ基
、プロポキシ基、ブトキシ基などのアルコキシ基、塩素
原子、臭素原子などのハロゲン原子、ジメチルアミノ基
、ジエチルアミノ基などのジアルキルアミノ基、トリフ
ルオロメチル基などのハロメチル基、ニトロ基、シアノ
基、カルボキシル基またはそのエステル、水酸基、−Ｓ
Ｏ３Ｎａ などのスルホン酸塩基などが挙げられる。Substituents on the hydrocarbon ring group or heterocyclic group of Y2 or R5 or the ring formed by R5 and R6 include alkyl groups such as methyl group, ethyl group, propyl group, butyl group, methoxy group, ethoxy group, etc. alkoxy groups such as propoxy groups and butoxy groups, halogen atoms such as chlorine atoms and bromine atoms, dialkylamino groups such as dimethylamino groups and diethylamino groups, halomethyl groups such as trifluoromethyl groups, nitro groups, cyano groups, and carboxyl groups. group or its ester, hydroxyl group, -S
Examples include sulfonic acid groups such as O3Na.
【００５８】Ｒ４のフェニル基の置換体としては塩素原
子または臭素原子などのハロゲン原子が例示できる。Ｒ
７またはＲ９における炭化水素基の代表例としては、メ
チル基、エチル基、プロピル基、ブチル基などのアルキ
ル基、フェニル基などのアリール基またはこれらの置換
体が例示できる。Ｒ７またはＲ９の炭化水素基における
置換基としては、メチル基、エチル基、プロピル基、ブ
チル基などのアルキル基、メトキシ基、エトキシ基、プ
ロポキシ基、ブトキシ基などのアルコキシ基、塩素原子
、臭素原子などのハロゲン原子、水酸基、ニトロ基など
が例示できる。Examples of substituents for the phenyl group of R4 include halogen atoms such as chlorine atoms and bromine atoms. R
Representative examples of the hydrocarbon group in 7 or R9 include alkyl groups such as methyl, ethyl, propyl and butyl groups, aryl groups such as phenyl, and substituted products thereof. Substituents for the hydrocarbon group of R7 or R9 include alkyl groups such as methyl, ethyl, propyl, and butyl; alkoxy groups such as methoxy, ethoxy, propoxy, and butoxy; chlorine and bromine; Examples include halogen atoms, hydroxyl groups, and nitro groups.
【００５９】Ａｒ１またはＡｒ２における炭化水素環基
としては、フェニル基、ナフチル基などがその代表例で
あり、また、これらの基における置換基としては、メチ
ル基、エチル基、プロピル基、ブチル基などのアルキル
基、メトキシ基、エトキシ基、プロポキシ基、ブトキシ
基などのアルコキシ基、ニトロ基、塩素原子、臭素原子
などのハロゲン原子、シアノ基、ジメチルアミノ基、ジ
エチルアミノ基などのジアルキルアミノ基などが例示で
きる。Representative examples of the hydrocarbon ring group in Ar1 or Ar2 include phenyl group, naphthyl group, etc., and substituents on these groups include methyl group, ethyl group, propyl group, butyl group, etc. Examples include alkyl groups such as methoxy groups, ethoxy groups, propoxy groups, butoxy groups, halogen atoms such as nitro groups, chlorine atoms, bromine atoms, and dialkylamino groups such as cyano groups, dimethylamino groups, and diethylamino groups. can.
【００６０】また、Ｘの中では特に水酸基が適当である
。上記カップラー残基の中でも好ましいのは上記一般式
（２），（５），（６），（７），（８）および（９）
で示されるものであり、この中でも一般式におけるＸが
水酸基のものが好ましい。また、この中でも化８（一般
式（１０））で表わされるカップラー残基が好ましく、
さらに好ましくは化９（一般式（１１））で表わされる
カップラー残基である。Among X, hydroxyl group is particularly suitable. Among the above coupler residues, the above general formulas (2), (5), (6), (7), (8) and (9) are preferable.
Among these, those in which X in the general formula is a hydroxyl group are preferred. Also, among these, a coupler residue represented by chemical formula 8 (general formula (10)) is preferable,
More preferred is a coupler residue represented by Chemical Formula 9 (general formula (11)).
【００６１】さらにまた、上記好ましいカップラー残基
の中でも化１０（一般式（１２）または（１３））で表
わされるものが適当である。Furthermore, among the above-mentioned preferred coupler residues, those represented by Formula 10 (general formula (12) or (13)) are suitable.
【化８】[Chemical formula 8]
【化９】[Chemical formula 9]
【化１０】[Chemical formula 10]
【００６２】前記一般式（Ｉ）又は一般式（ＩＩ）で示
される化合物は電荷発生物質１重量部に対して０．０１
重量部以上用いるのが適当であり、好ましくは０．０５
重量部以上、更に好ましくは０．１重量部以上である。
バインダー樹脂は使用しなくてもかまわないが、使用し
た方が、本発明の効果を更に高めることができる。その
際のバインダー樹脂の使用量は電荷発生物質１重量部に
対して０．０２〜３重量部が好ましく、更に好ましくは
０．２〜２重量部である。The compound represented by the general formula (I) or general formula (II) is used in an amount of 0.01 part by weight per 1 part by weight of the charge generating substance.
It is appropriate to use 0.05 parts by weight or more, preferably 0.05 parts by weight or more.
The amount is at least 0.1 part by weight, more preferably at least 0.1 part by weight. Although the binder resin may not be used, the effects of the present invention can be further enhanced if it is used. The amount of binder resin used in this case is preferably 0.02 to 3 parts by weight, more preferably 0.2 to 2 parts by weight, per 1 part by weight of the charge generating substance.
【００６３】電荷発生層は、一般式（Ｉ）又は（ＩＩ）
で示される化合物と電荷発生物質を必要ならばバインダ
ー樹脂とともに、テトラヒドロフラン、シクロヘキサノ
ン、ジオキサン、ジクロルエタン等の溶媒を用いてボー
ルミル、アトライター、サンドミルなどにより分散し、
分散液を適度に希釈して塗布することにより形成できる
。塗布は、浸漬塗工法やスプレーコート、ビードコート
法などを用いて行なうことができる。電荷発生層の膜厚
は、０．０１〜５μｍ程度であり、好ましくは０．１〜
２μｍである。The charge generation layer has the general formula (I) or (II)
Disperse the compound represented by and a charge generating substance together with a binder resin if necessary using a ball mill, attritor, sand mill, etc. using a solvent such as tetrahydrofuran, cyclohexanone, dioxane, dichloroethane, etc.
It can be formed by diluting a dispersion liquid appropriately and applying it. Application can be performed using a dip coating method, a spray coating method, a bead coating method, or the like. The thickness of the charge generation layer is approximately 0.01 to 5 μm, preferably 0.1 to 5 μm.
It is 2 μm.
【００６４】電荷輸送層１７は、電荷輸送物質およびバ
インダー樹脂を適当な溶剤に溶解ないし分散し、これを
塗布、乾燥することにより形成できる。電荷輸送物質に
は、正孔輸送物質と電子輸送物質とがある。The charge transport layer 17 can be formed by dissolving or dispersing a charge transport substance and a binder resin in a suitable solvent, coating the solution, and drying the solution. Charge transport materials include hole transport materials and electron transport materials.
【００６５】電子輸送物質としては、たとえば、クロル
アニル、ブロムアニル、テトラシアノエチレン、テトラ
シアノキノンジメタン、２，４，７−トリニトロ−９−
フルオレノン、２，４，５，７−テトラニトロ−９−フ
ルオレノン、２，４，５，７−テトラニトロキサントン
、２，４，８−トリニトロチオキサントン、２，６，８
−トリニトロ−４Ｈ−インデノ〔１，２−ｂ〕チオフェ
ン−４−オン、１，３，７−トリニトロジベンゾチオフ
ェノン−５，５−ジオキサイドなどの電子受容性物質が
挙げられる。正孔輸送物質としては、以下の一般式で表
わされる電子供与性物質等が挙げられ、良好に用いられ
る。Examples of the electron transport substance include chloranil, bromoanil, tetracyanoethylene, tetracyanoquinone dimethane, 2,4,7-trinitro-9-
Fluorenone, 2,4,5,7-tetranitro-9-fluorenone, 2,4,5,7-tetranitroxanthone, 2,4,8-trinitrothioxanthone, 2,6,8
Electron-accepting substances such as -trinitro-4H-indeno[1,2-b]thiophen-4-one and 1,3,7-trinitrodibenzothiophenone-5,5-dioxide can be mentioned. Examples of the hole-transporting substance include electron-donating substances represented by the following general formula, which are suitably used.
【００６６】[0066]
【化１１】
（式中、Ｒ１，Ｒ２，Ｒ３およびＲ４は水素原子、置換
もしくは無置換のアリール基を表わし、Ａｒ１は置換又
は無置換のアリール基を表わし、Ａｒ１とＲ１は共用で
環を形成してもよく、またｎは０又は１の整数である。
）[Formula 11] (In the formula, R1, R2, R3 and R4 represent a hydrogen atom or a substituted or unsubstituted aryl group, Ar1 represents a substituted or unsubstituted aryl group, and Ar1 and R1 jointly form a ring. and n is an integer of 0 or 1.)
【００６７】[0067]
【化１２】
（但し、Ｒ１は低級アルキル基、低級アルコキシ基又は
ハロゲン原子を表わし、ｎは０〜４の整数を表わし、Ｒ
２，Ｒ３は同一でも異なっていてもよく、水素原子、低
級アルキル基、低級アルコキシ基又はハロゲン原子を表
わす。）[Chemical formula 12] (However, R1 represents a lower alkyl group, a lower alkoxy group, or a halogen atom, n represents an integer of 0 to 4, and R
2 and R3 may be the same or different and represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a halogen atom. )
【００６８】[0068]
【化１３】
（式中、Ｒ１は炭素数１〜１１のアルキル基、置換又は
非置換のフェニル基あるいは複素環残基を表わし、Ｒ２
，Ｒ３はそれぞれ同一でも異なっていてもよく、水素原
子、低級アルキル基、Ｃ１〜Ｃ４のヒドロキシアルキル
基、Ｃ１〜Ｃ４のクロルアルキル基、あるいは置換又は
非置換のアラルキル基を表わし、またＲ２とＲ３は共同
で窒素を含む複素環を形成してもよく、Ｒ４，Ｒ５はそ
れぞれ同一でも異なっていてもよく、水素原子、低級ア
ルキル基、低級アルコキシ基又はハロゲン原子を表わす
。）キル基、低級アルコキシ基又はハロゲン原子を表わ
す。）embedded image (wherein, R1 represents an alkyl group having 1 to 11 carbon atoms, a substituted or unsubstituted phenyl group, or a heterocyclic residue, and R2
, R3 may be the same or different, and each represents a hydrogen atom, a lower alkyl group, a C1-C4 hydroxyalkyl group, a C1-C4 chloroalkyl group, or a substituted or unsubstituted aralkyl group, and R2 and R3 may jointly form a nitrogen-containing heterocycle, and R4 and R5 may each be the same or different and represent a hydrogen atom, a lower alkyl group, a lower alkoxy group, or a halogen atom. ) represents a kill group, a lower alkoxy group, or a halogen atom. )
【００６９】[0069]
【化１４】
（式中、Ｒ１は水素原子又はハロゲン原子を表わし、Ｒ
２は置換または非置換の芳香族残基あるいは複素環残基
（但し前記置換基はハロゲン、シアノ、ジ低級アルキル
アミノ、置換又は非置換のジアラルキルアミノ基、低級
アルキル基、低級アルコキシ基及びニトロ基よりなる群
から選ばれる。）を表わす。）embedded image (wherein, R1 represents a hydrogen atom or a halogen atom, and R
2 is a substituted or unsubstituted aromatic residue or a heterocyclic residue (however, the substituents include halogen, cyano, di-lower alkylamino, substituted or unsubstituted dialkylamino group, lower alkyl group, lower alkoxy group, and nitro (selected from the group consisting of the following). )
【００７０】[0070]
【化１５】
（式中、Ｒ１，Ｒ３は水素原子、低級アルキル基、低級
アルコキシ基、あるいはジ低級アルキルアミノ基を表わ
し、Ｒ２は水素原子、低級アルキル基、低級アルコキシ
基、ハロゲン原子あるいはニトロ基を表わし、ｎは０又
は１を表わす。）(In the formula, R1 and R3 represent a hydrogen atom, a lower alkyl group, a lower alkoxy group, or a di-lower alkylamino group, and R2 represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom, or a nitro group. (n represents 0 or 1.)
【００７１】[0071]
【化１６】
（式中、Ｒはカルバゾリル基、ピリジル基、チエニル基
、インドリル基又はフリル基、あるいはそれぞれ置換ま
たは非置換のフェニル基、スチリル基、ナフチル基又は
アントリル基（但し前記置換基はジ低級アルキルアミノ
基、低級アルキル基、低級アルコキシ基、ハロゲン原子
、アラルキルアミノ基又は、アミノ基からなる群から選
ばれる）を表わす。）embedded image (wherein R is a carbazolyl group, pyridyl group, thienyl group, indolyl group, or furyl group, or a substituted or unsubstituted phenyl group, styryl group, naphthyl group, or anthryl group (provided that the above substituent is (selected from the group consisting of a lower alkylamino group, a lower alkyl group, a lower alkoxy group, a halogen atom, an aralkylamino group, or an amino group).
【００７２】[0072]
【化１７】
（式中、Ｒ１，Ｒ２，Ｒ３は同一でも異なっていてもよ
く、水素原子、低級アルキル基、低級アルコキシ基、フ
ェニル基、フェノキシ基、またはハロゲン原子を表わす
。）embedded image (In the formula, R1, R2, and R3 may be the same or different and represent a hydrogen atom, a lower alkyl group, a lower alkoxy group, a phenyl group, a phenoxy group, or a halogen atom.)
【００７３】[0073]
【化１８】
（式中、Ｒ１は水素原子、ハロゲン原子、シアノ基、低
級アルキル基を表わし、Ａｒは[Image Omitted] (In the formula, R1 represents a hydrogen atom, a halogen atom, a cyano group, or a lower alkyl group, and Ar is
【００７４】[0074]
【化１９】[Chemical formula 19]
【００７５】[0075]
【化２０】
（ただし、化１９、化２０において、Ｒ２，Ｒ３，Ｒ６
は水素原子、置換又は無置換の低級アルキル基あるいは
置換又は無置換のベンジル基を表わし、Ｒ４，Ｒ５は水
素原子、ハロゲン原子、低級アルキル基あるいは低級ア
ルコキシ基又はジ低級アルキルアミノ基を表わす。）[Chemical Formula 20] (However, in Chemical Formula 19 and Chemical Formula 20, R2, R3, R6
represents a hydrogen atom, a substituted or unsubstituted lower alkyl group, or a substituted or unsubstituted benzyl group, and R4 and R5 represent a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, or a di-lower alkylamino group. )
【
００７６】[
0076
【化２１】
（式中、Ｒ１，Ｒ２．Ｒ３．Ｒ４．Ｒ６は水素原子、ハ
ロゲン原子、低級アルキル基、低級アルコキシ基、置換
又は無置換のジ低級アルキルアミノ基又はジベンジルア
ミノ基を表わし、Ｒ５は低級アルキル基又はベンジル基
を表わす。）embedded image (wherein R1, R2.R3.R4.R6 represent a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, a substituted or unsubstituted di-lower alkylamino group or a dibenzylamino group, R5 represents a lower alkyl group or a benzyl group.)
【００７７】[0077]
【化２２】
（式中、Ａｒはナフタレン環、アントラセン環、スチリ
ル基及びそれらの置換体、あるいはピリジン環、フラン
環、チオフェン環を表わし、Ｒは低級アルキル基又はベ
ンジル基を表わす。）[Image Omitted] (In the formula, Ar represents a naphthalene ring, anthracene ring, styryl group, or a substituted product thereof, or a pyridine ring, a furan ring, or a thiophene ring, and R represents a lower alkyl group or a benzyl group.)
【００７８】[0078]
【化２３】
（式中、Ｒ１は低級アルキル基、２−ヒドロキシエチル
基又は２−クロロエチル基を表わし、Ｒ２は低級アルキ
ル基、ベンジル基又はフェニル基を表わし、Ｒ３は水素
原子、ハロゲン原子、低級アルキル基、低級アルコキシ
基、ジ低級アルキルアミノ基又はニトロ基を表わす。）
(In the formula, R1 represents a lower alkyl group, 2-hydroxyethyl group, or 2-chloroethyl group, R2 represents a lower alkyl group, benzyl group, or phenyl group, and R3 represents a hydrogen atom, a halogen atom, a lower (represents an alkyl group, lower alkoxy group, di-lower alkylamino group, or nitro group)
【００７９】[0079]
【化２４】
（式中、Ｒ１は水素原子、低級アルキル基、クロルエチ
ル基又はヒドロキシエチル基を表わし、Ｒ２は水素原子
又はハロゲン原子を表わし、Ｒ３は低級アルキル基、ジ
低級アルキルアミノ基、ジアリールアミノ基、置換又は
無置換のスチリル基、置換又は無置換の芳香環残基（芳
香環又はベンゼン環、ナフタレン環、アントラセン環
等）、置換又は無置換の複素環残基（複素環はピリジン
環、キノキサリン環、カルバゾール環等）を表わす。）
embedded image (wherein, R1 represents a hydrogen atom, a lower alkyl group, a chloroethyl group, or a hydroxyethyl group, R2 represents a hydrogen atom or a halogen atom, and R3 represents a lower alkyl group, a di-lower alkylamino group, a diarylamino group) group, substituted or unsubstituted styryl group, substituted or unsubstituted aromatic ring residue (aromatic ring or benzene ring, naphthalene ring, anthracene ring)
), substituted or unsubstituted heterocyclic residues (heterocycles include pyridine rings, quinoxaline rings, carbazole rings, etc.). )
【００８０】[0080]
【化２５】
（式中、Ｒ１は低級アルキル基を表わし、Ｒ２は低級ア
ルキル基、ジ低級アルキルアミノ基、ジアリールアミノ
基、置換又は無置換のスチリル基、置換又は無置換の芳
香環残基（芳香環はベンゼン環、ナフタレン環、アント
ラセン環等）、置換又は無置換の複素環残基（複素環は
ピリジン環、キノキサリン環、カルバゾール環等）を表
わす。）embedded image (wherein, R1 represents a lower alkyl group, R2 is a lower alkyl group, a di-lower alkylamino group, a diarylamino group, a substituted or unsubstituted styryl group, a substituted or unsubstituted aromatic ring residue ( The aromatic ring represents a benzene ring, naphthalene ring, anthracene ring, etc.), and a substituted or unsubstituted heterocyclic residue (heterocycle represents a pyridine ring, quinoxaline ring, carbazole ring, etc.)
【００８１】[0081]
【化２６】
（式中、Ｒ１，Ｒ２は同一でも異なっていてもよく、水
素原子、低級アルキル基、ヒドロキシ低級アルキル基、
クロル低級アルキル基、アルキルの炭素数１〜２のアシ
ル基、アルキルの炭素数５〜６のシクロアルキル基、あ
るいは置換又は非置換のアラルキル基を表わす。）embedded image (wherein R1 and R2 may be the same or different, a hydrogen atom, a lower alkyl group, a hydroxy lower alkyl group,
It represents a chloro lower alkyl group, an acyl group having 1 to 2 carbon atoms in alkyl, a cycloalkyl group having 5 to 6 carbon atoms in alkyl, or a substituted or unsubstituted aralkyl group. )
【０
０８２】0
082]
【化２７】
（式中、Ｒ１，Ｒ３及びＲ４は水素原子、アミノ基、ア
ルコキシ基、チオアルコキシ基、アリールオキシ基、メ
チレンジオキシ基、置換もしくは無置換のアルキル基、
ハロゲン原子又は置換もしくは無置換のアリール基を、
Ｒ２は水素原子、アルコキシ基、置換もしくは無置換の
アルキル基又はハロゲンを表わす。但し、Ｒ１，Ｒ２，
Ｒ３およびＲ４がすべて水素原子である場合は除く。ま
たｋ，ｔ，ｍ及びｎは１，２，３又は４の整数であり、
各々が２，３又は４の整数の時は前記Ｒ１，Ｒ２，Ｒ３
およびＲ４は同一でも異なっていてもよい。embedded image (wherein R1, R3 and R4 are hydrogen atoms, amino groups, alkoxy groups, thioalkoxy groups, aryloxy groups, methylenedioxy groups, substituted or unsubstituted alkyl groups,
A halogen atom or a substituted or unsubstituted aryl group,
R2 represents a hydrogen atom, an alkoxy group, a substituted or unsubstituted alkyl group, or a halogen. However, R1, R2,
Except when R3 and R4 are all hydrogen atoms. Further, k, t, m and n are integers of 1, 2, 3 or 4,
When each is an integer of 2, 3 or 4, the above R1, R2, R3
and R4 may be the same or different.
【００８３】[0083]
【化２８】
Ａ−ＣＨ２ＣＨ２−Ａｒ１−ＣＨ２ＣＨ２−Ａ（式中、
Ａｒ１は置換もしくは無置換の芳香族炭化水素基または
複素環基を表わし、Ａは置換もしくは無置換のＮ−置換
カルバゾリル基または−Ａｒ２−Ｎ（Ｒ１）（Ｒ２）（
ただし、Ａｒ２は置換もしくは無置換の芳香族炭化水素
基または複素環基であり、Ｒ１及びＲ２は置換もしくは
無置換のアルキル基、または置換もしくは無置換のアリ
ール基である。）を表わす。）これらの電荷輸送物質は
、単独又は２種以上混合して用いられる。embedded image A-CH2CH2-Ar1-CH2CH2-A (in the formula,
Ar1 represents a substituted or unsubstituted aromatic hydrocarbon group or a heterocyclic group, and A represents a substituted or unsubstituted N-substituted carbazolyl group or -Ar2-N(R1)(R2)(
However, Ar2 is a substituted or unsubstituted aromatic hydrocarbon group or a heterocyclic group, and R1 and R2 are a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group. ). ) These charge transport materials may be used alone or in a mixture of two or more.
【００８４】バインダー樹脂としてはポリスチレン、ス
チレン−アクリロニトリル共重合体、スチレン−ブタジ
エン共重合体、スチレン−無水マレイン酸共重合体、ポ
リエステル、ポリ塩化ビニル、塩化ビニル−酢酸ビニル
共重合体、ポリ酢酸ビニル、ポリ塩化ビニリデン、ポリ
アリレート樹脂、フェノキシ樹脂、ポリカーボネート、
酢酸セルロース樹脂、エチルセルロース樹脂、ポリビニ
ルブチラール、ポリビニルホルマール、ポリビニルトル
エン、ポリ−Ｎ−ビニルカルバゾール、アクリル樹脂、
シリコーン樹脂、エポキシ樹脂、メラミン樹脂、ウレタ
ン樹脂、フェノール樹脂、アルキッド樹脂等の熱可塑性
または熱硬化性樹脂が挙げられる。Binder resins include polystyrene, styrene-acrylonitrile copolymer, styrene-butadiene copolymer, styrene-maleic anhydride copolymer, polyester, polyvinyl chloride, vinyl chloride-vinyl acetate copolymer, and polyvinyl acetate. , polyvinylidene chloride, polyarylate resin, phenoxy resin, polycarbonate,
Cellulose acetate resin, ethyl cellulose resin, polyvinyl butyral, polyvinyl formal, polyvinyltoluene, poly-N-vinylcarbazole, acrylic resin,
Examples include thermoplastic or thermosetting resins such as silicone resins, epoxy resins, melamine resins, urethane resins, phenolic resins, and alkyd resins.
【００８５】溶剤としては、テトラヒドロフラン、ジオ
キサン、トルエン、モノクロルベンゼン、ジクロルエタ
ン、塩化メチレンなどが用いられる。電荷輸送層１７の
厚さは５〜１００μｍ程度が適当である。また、本発明
において電荷輸送層１７中に可塑剤やレベリング剤を添
加してもよい。可塑剤としては、ジブチルフタレート、
ジオクチルフタレートなど一般の樹脂の可塑剤として使
用されているものがそのまま使用でき、その使用量は、
バインダー樹脂に対して０〜３０重量％程度が適当であ
る。レベリング剤としては、ジメチルシリコーンオイル
、メチルフェニルシリコーンオイルなどのシリコーンオ
イル類が使用され、その使用量はバインダー樹脂に対し
て、０〜１重量％程度が適当である。[0085] As the solvent, tetrahydrofuran, dioxane, toluene, monochlorobenzene, dichloroethane, methylene chloride, etc. are used. The appropriate thickness of the charge transport layer 17 is about 5 to 100 μm. Further, in the present invention, a plasticizer or a leveling agent may be added to the charge transport layer 17. As a plasticizer, dibutyl phthalate,
Those used as plasticizers for general resins such as dioctyl phthalate can be used as is, and the amount used is as follows:
A suitable amount is about 0 to 30% by weight based on the binder resin. As the leveling agent, silicone oils such as dimethyl silicone oil and methylphenyl silicone oil are used, and the appropriate amount thereof is about 0 to 1% by weight based on the binder resin.
【００８６】支持体１１と電荷発生層１５との間に設け
られる下引層１３は本発明の効果をいっそう向上すると
共に、接着性を向上する目的で設けられ、その材料とし
てはＳｉＯ、Ａｌ２Ｏ３、シランカップリング剤、チタ
ンカップリング剤、クロムカップリング剤等の無機材料
やポリアミド樹脂、アルコール可溶性ポリアミド樹脂、
水溶性ポリビニルブチラール、ポリビニルブチラール、
ＰＶＡ等の接着性の良いバインダー樹脂などが使用され
る。その他、前記接着性の良い樹脂にＺｎＯ，ＴｉＯ２
，ＺｎＳ等を分散したものも使用できる。下引層の形成
法としては無機材料単独の場合はスパッタリング、蒸着
等の方法が、また有機材料を用いた場合は通常の塗布法
が採用される。なお下引層の厚さは５μｍ以下が適当で
ある。The undercoat layer 13 provided between the support 11 and the charge generation layer 15 is provided for the purpose of further improving the effects of the present invention and improving adhesion, and its materials include SiO, Al2O3, Inorganic materials such as silane coupling agents, titanium coupling agents, chromium coupling agents, polyamide resins, alcohol-soluble polyamide resins,
Water-soluble polyvinyl butyral, polyvinyl butyral,
A binder resin with good adhesive properties such as PVA is used. In addition, ZnO, TiO2 are added to the resin with good adhesive properties.
, ZnS, etc. can also be used. As a method for forming the undercoat layer, methods such as sputtering and vapor deposition are used when an inorganic material alone is used, and when an organic material is used, a normal coating method is used. Note that the thickness of the undercoat layer is suitably 5 μm or less.
【００８７】保護層１９は感光体の表面保護の目的で設
けられ、これに使用される材料としてＡＢＳ樹脂、ＡＣ
Ｓ樹脂、オレフィン〜ビニルモノマー共重合体、塩素化
ポリエーテル、アリル樹脂、フェノール樹脂、ポリアセ
タール、ポリアミド、ポリアミドイミド、ポリアクリレ
ート、ポリアリルスルホン、ポリブチレン、ポリブチレ
ンテレフタレート、ポリカーボネート、ポリエーテルス
ルホン、ポリエチレン、ポリエチレンテレフタレート、
ポリイミド、アクリル樹脂、ポリメチルペンテン、ポリ
プロピレン、ポリフェニレンオキシド、ポリスルホン、
ポリスチレン、ＡＳ樹脂、ブタジエン−スチレン共重合
体、ポリウレタン、ポリ塩化ビニル、ポリ塩化ビニデン
、エポキシ樹脂等の樹脂が挙げられる。保護層にはその
他、耐摩耗性を向上する目的でポリテトラフルオロエチ
レンのような弗素樹脂、シリコーン樹脂、及びこれら樹
脂に酸化チタン、酸化錫、チタン酸カリウム等の無機材
料を分散したもの等を添加することができる。保護層の
形成法としては通常の塗布法が採用される。なお保護層
の厚さは０．５〜１０μｍ程度が適当である。The protective layer 19 is provided for the purpose of protecting the surface of the photoreceptor, and materials used for this include ABS resin, AC
S resin, olefin-vinyl monomer copolymer, chlorinated polyether, allyl resin, phenol resin, polyacetal, polyamide, polyamideimide, polyacrylate, polyallylsulfone, polybutylene, polybutylene terephthalate, polycarbonate, polyethersulfone, polyethylene, polyethylene terephthalate,
Polyimide, acrylic resin, polymethylpentene, polypropylene, polyphenylene oxide, polysulfone,
Examples include resins such as polystyrene, AS resin, butadiene-styrene copolymer, polyurethane, polyvinyl chloride, polyvinidene chloride, and epoxy resin. In addition, the protective layer may include fluororesins such as polytetrafluoroethylene, silicone resins, and inorganic materials such as titanium oxide, tin oxide, potassium titanate, etc. dispersed in these resins for the purpose of improving wear resistance. Can be added. A normal coating method is adopted as a method for forming the protective layer. Note that the thickness of the protective layer is suitably about 0.5 to 10 μm.
【００８８】更に本発明では電荷輸送層１７と保護層１
９との間に別の中間層（図示せず）を設けることも可能
である。Furthermore, in the present invention, the charge transport layer 17 and the protective layer 1
It is also possible to provide another intermediate layer (not shown) between it and 9.
【００８９】[0089]
【実施例】次に、実施例によって、本発明をさらに詳細
に説明するが、本発明は以下の実施例に限定されるもの
ではない。なお、実施例中使用する部は、すべて重量部
を表わす。EXAMPLES Next, the present invention will be explained in more detail with reference to examples, but the present invention is not limited to the following examples. Note that all parts used in the examples represent parts by weight.
【００９０】実施例１
アルミニウムを蒸着したポリエチレンテレフタレート・
フィルム上に、下記組成の電荷発生層塗工液、電荷輸送
層塗工液を順次、塗布・乾燥して各々０．２μｍ厚の電
荷発生層および２２μｍ厚の電荷輸送層を形成し、本発
明の電子写真感光体を作成した。
〔電荷発生層塗工液〕
下記構造式の電荷発生物質
５部Example 1 Polyethylene terephthalate coated with aluminum
A charge generation layer coating liquid and a charge transport layer coating liquid having the following compositions were sequentially applied and dried on the film to form a charge generation layer with a thickness of 0.2 μm and a charge transport layer with a thickness of 22 μm, respectively. An electrophotographic photoreceptor was prepared. [Charge generation layer coating liquid] Charge generation substance with the following structural formula
5th part
【化２９】 下記構造式の一般式（Ｉ）の化合物[C29] Compound of general formula (I) of the following structural formula
【化３０】
ポリビニルブチラール樹脂
２部 （電気化学工業（株）製デンカブ
チラール＃４０００−１） シクロヘキサノン
３００部 ２−ブ
タノン
１２０部〔電荷輸送層塗工液〕
下記構造式の電荷輸送物質
９部[Chemical formula 30] Polyvinyl butyral resin
2 parts (Denka Butyral #4000-1 manufactured by Denki Kagaku Kogyo Co., Ltd.) Cyclohexanone
300 parts 2-butanone
120 parts [Charge transport layer coating liquid] Charge transport substance having the following structural formula
9th part
【化３１】
ポリカーボネート（帝人化成（株）製 パンライト
Ｌ−１２５０） １０部 テト
ラヒドロフラン
８１部[Chemical formula 31] Polycarbonate (Panlite L-1250 manufactured by Teijin Kasei Ltd.) 10 parts Tetrahydrofuran
81 copies
【００９１】実施例２
実施例１と同じ支持体上に、下記組成の下引層塗工液、
電荷発生層塗工液および電荷輸送層塗工液を順次、塗布
・乾燥して各々０．３μｍの下引層、０．２μｍの電荷
発生層および２０μｍの電荷輸送層を形成し、本発明の
電子写真感光体を作成した。
〔下引層塗工液〕
水溶性ポリビニルブチラールの２５％水溶液（積水
化学工業（株）製 エスレック Ｗ−２０１）
５０部 水
１５０部 メタノール
２００部〔電荷発
生層塗工液〕
下記構造式の電荷発生物質
５部Example 2 On the same support as in Example 1, a subbing layer coating solution having the following composition,
A charge generation layer coating solution and a charge transport layer coating solution were sequentially applied and dried to form a subbing layer of 0.3 μm, a charge generation layer of 0.2 μm, and a charge transport layer of 20 μm, respectively. An electrophotographic photoreceptor was created. [Undercoat layer coating liquid] 25% aqueous solution of water-soluble polyvinyl butyral (S-LEC W-201 manufactured by Sekisui Chemical Co., Ltd.)
50 parts water
150 parts methanol
200 parts [Charge generation layer coating liquid] Charge generation substance having the following structural formula
5th part
【化３２】
下記構造式の一般式（Ｉ）の化合物
３部[Chemical formula 32] Compound of general formula (I) of the following structural formula
Part 3
【化３３】
シクロヘキサノン
２５０部 ２−ブタノン
１００部〔
電荷輸送層塗工液〕
下記構造式の電荷発生物質
１０部[Chemical formula 33] Cyclohexanone
250 parts 2-butanone
100 copies [
Charge transport layer coating liquid] Charge generating substance with the following structural formula
10 copies
【化３４】
ポリカーボネート（帝人化成（株）製パンライトＫ−１
３００） １０部テトラヒドラフラン
７５部[Chemical formula 34] Polycarbonate (Panlite K-1 manufactured by Teijin Kasei Ltd.)
300) 10 parts tetrahydrofuran
75 copies
【００９
２】実施例３ハステロイ導電層を設けたポリエチレンテ
レフタレートフィルム上に、下記組成の下引層塗工液、
電荷発生層塗工液および電荷輸送層塗工液を順次・塗布
・乾燥して、各々２μｍの下引層、０．３μｍの電荷発
生層および１８μｍの電荷輸送層を形成し、本発明の電
子写真感光体を作成した。
〔下引層塗工液〕
二酸化チタン
１０部 ポリエステル（東洋紡
績（株）製バイロン２００）
１部 トルイレン−２，４−
ジイソシアネート
０．２部 ２−ブタノ
ン
１００部 ４−メチル−２−ペンタノン
７０部〔電荷発生層塗
工液〕
下記構造式の電荷輸送物質
５部009
2] Example 3 On a polyethylene terephthalate film provided with a Hastelloy conductive layer, a subbing layer coating solution having the following composition,
A charge generation layer coating solution and a charge transport layer coating solution were sequentially coated and dried to form a subbing layer of 2 μm, a charge generation layer of 0.3 μm, and a charge transport layer of 18 μm, respectively. A photographic photoreceptor was created. [Undercoat layer coating liquid] Titanium dioxide
10 parts Polyester (Vylon 200 manufactured by Toyobo Co., Ltd.)
1 part toluylene-2,4-
Diisocyanate
0.2 parts 2-butanone
100 parts 4-methyl-2-pentanone
70 parts [Charge generation layer coating liquid] Charge transport substance having the following structural formula
5th part
【化３５】
下記構造式の一般式（Ｉ）の化合物
１部[Chemical formula 35] Compound of general formula (I) of the following structural formula
Part 1
【化３６】
ポリビニルブチラール（ＵＣＣ製ＸＹＨＬ）
２部 シクロヘキサノン
２００部 テトラヒドロ
フラン
７５
部〔電荷輸送層塗工液〕
下記構造式の電荷輸送物質
８部[Chemical formula 36] Polyvinyl butyral (XYHL manufactured by UCC)
Part 2 Cyclohexanone
200 parts tetrahydrofuran
75
Part [Charge transport layer coating liquid] Charge transport substance having the following structural formula
Part 8
【化３７】
ポリアリレート（ユニチカ（株）製 Ｕ−１００）
１０部 テトラヒドロフラン
８２部[Chemical formula 37] Polyarylate (U-100 manufactured by Unitika Co., Ltd.)
10 parts Tetrahydrofuran
82 copies
【００９３】実施例４
厚さ０．２ｍｍのアルミニウム板上に、下記組成の電荷
発生層塗工液および電荷輸送層塗工液を順次、塗布・乾
燥して各々２．５μｍの電荷発生層および１７μｍの電
荷輸送層を形成し、本発明の電子写真感光体を作成した
。〔電荷発生層塗工液〕
下記構造式の電荷発生物質
４部Example 4 A charge generation layer coating liquid and a charge transport layer coating liquid having the following compositions were sequentially coated and dried on an aluminum plate having a thickness of 0.2 mm to form a charge generation layer and a charge transport layer having a thickness of 2.5 μm, respectively. A charge transport layer having a thickness of 17 μm was formed to produce an electrophotographic photoreceptor of the present invention. [Charge generation layer coating liquid] Charge generation substance with the following structural formula
4th part
【化３８】
下記構造式の一般式（Ｉ）の化合物
４部[Chemical formula 38] Compound of general formula (I) of the following structural formula
4th part
【化３９】
ポリエステル（東洋紡績（株）製バイロン３００）
１部 テトラヒドロフラン
３００部〔電荷輸送層塗工液〕
下記構造式の電荷輸送物質
１０部[Chemical formula 39] Polyester (Vylon 300 manufactured by Toyobo Co., Ltd.)
1 part Tetrahydrofuran
300 parts [Charge transport layer coating liquid] Charge transport substance having the following structural formula
10 copies
【化４０】
ポリカーボネート（ＧＥ社製 レキサン−１４１）
１０部 塩化メチレン
９０部[Chemical formula 40] Polycarbonate (Lexan-141 manufactured by GE)
10 parts methylene chloride
90 copies
【００９４】実
施例５
厚さ０．１ｍｍ電鋳ニッケル板上に、下記組成の下引層
塗工液、電荷発生層塗工液、電荷輸送層塗工液および保
護層塗工液を順次、塗布・乾燥して各々０．３μｍの下
引層、０．２μｍの電荷発生層、１８μｍの電荷輸送層
および３μｍの保護層を形成し、本発明の電子写真感光
体を作成した。
〔下引層塗工液〕
ポリビニルアルコール（電気化学工業（株）製デン
カポバールＨ−２０） ２部 水
１００部 メタノール
１００部〔電
荷発生層塗工液〕
下記構造式の電荷発生物質
４部Example 5 On an electroformed nickel plate having a thickness of 0.1 mm, a subbing layer coating liquid, a charge generation layer coating liquid, a charge transport layer coating liquid and a protective layer coating liquid having the following compositions were sequentially applied. A subbing layer of 0.3 μm, a charge generation layer of 0.2 μm, a charge transport layer of 18 μm, and a protective layer of 3 μm were formed by coating and drying, thereby producing an electrophotographic photoreceptor of the present invention. [Undercoat layer coating liquid] Polyvinyl alcohol (Denka Poval H-20 manufactured by Denki Kagaku Kogyo Co., Ltd.) 2 parts Water
100 parts methanol
100 parts [Charge generation layer coating liquid] Charge generation substance having the following structural formula
4th part
【化４１】
下記構造式の一般式（Ｉ）の化合物
０．５部embedded image Compound of general formula (I) with the following structural formula
0.5 part
【化４２】
ポリサルホン（日産化学（株）製 Ｐ−１７０
０．５部 シクロヘキサノン
１００部 テトラヒドロフラン
１５０部〔電
荷輸送層塗工液〕
下記構造式の電荷輸送物質
９部[Chemical formula 42] Polysulfone (P-170 manufactured by Nissan Chemical Co., Ltd.)
0.5 part cyclohexanone
100 parts tetrahydrofuran
150 parts [Charge transport layer coating liquid] Charge transport substance having the following structural formula
9th part
【化４３】
ポリカーボネート（帝人化成（株）製パンライト
Ｋ−１３００） １０部
塩化メチレン
８０部〔保護層塗工液〕
スチレン〜メチルメタクリレート〜２−ヒドロキシエチ
ルメタクリレート〜トリフロロエチルメタクリレート共
重合体 ８
０部 酸化錫
８０部 トルエン
１７０部 ２−ブタノール
１００部[Chemical formula 43] Polycarbonate (Panlite manufactured by Teijin Kasei Ltd.)
K-1300) 10 copies
methylene chloride
80 parts [Protective layer coating liquid] Styrene - methyl methacrylate - 2-hydroxyethyl methacrylate - trifluoroethyl methacrylate copolymer 8
0 parts tin oxide
80 parts toluene
170 parts 2-butanol
100 copies
【００９５
】実施例６
実施例４と同じ支持体上に、下記組成の下引層塗工液、
電荷発生層塗工液および電荷輸送層塗工液を順次、塗布
・乾燥して各々２μｍの下引層、０．４μｍの電荷発生
層および２２μｍの電荷輸送層を形成し、本発明の電子
写真感光体を作成した。
〔下引層塗工液〕
二酸化チタン
６部 ポリビニルブチラー
ル（積水化学工業（株）製エスレックＢＬ−１）
１０部 ２−ブタノン
５０部
酢酸エチル
５０部〔電荷発生層塗工液〕
下記構造式の電荷発生物質
６部0095
Example 6 On the same support as in Example 4, a subbing layer coating solution having the following composition,
A charge generation layer coating solution and a charge transport layer coating solution were sequentially coated and dried to form a subbing layer of 2 μm, a charge generation layer of 0.4 μm, and a charge transport layer of 22 μm, respectively, and the electrophotography of the present invention was performed. A photoreceptor was created. [Undercoat layer coating liquid] Titanium dioxide
6 parts Polyvinyl butyral (S-LEC BL-1 manufactured by Sekisui Chemical Co., Ltd.)
10 parts 2-butanone
50 copies
Ethyl acetate
50 parts [Charge generation layer coating liquid] Charge generation substance having the following structural formula
Part 6
【化４４】
下記構造式の一般式（Ｉ）の化合物
０．４部embedded image Compound of general formula (I) with the following structural formula
0.4 parts
【化４５】
ポリエステル （東洋紡績（株）製 バイロン２
００）
２部 トルイレン−２，４−ジイソシアネート
０．１部 テトラヒドロフラン
２５０部 ４−メチル−２
−ペンタノン
１２５
部〔電荷輸送層塗工液〕
下記構造式の電荷輸送物質
１０部[Chemical formula 45] Polyester (byron 2 manufactured by Toyobo Co., Ltd.)
00)
2 parts Toluylene-2,4-diisocyanate
0.1 part tetrahydrofuran
250 parts 4-methyl-2
-Pentanone
125
Part [Charge transport layer coating liquid] Charge transport substance having the following structural formula
10 copies
【化４６】
ポリカーボネート（三菱瓦斯化学（株）製ポリカー
ボネートＺ） １２部 塩化メチレン
７０部 １，２−ジクロロエタン
３０部[Chemical formula 46] Polycarbonate (Polycarbonate Z manufactured by Mitsubishi Gas Chemical Co., Ltd.) 12 parts Methylene chloride
70 parts 1,2-dichloroethane
30 copies
【００９６】実施例７
φ６０のＡｌ円筒状支持体上に、下記組成の電荷発生層
塗工液、電荷輸送層塗工液、および保護層塗工液を順次
、塗布・乾燥して、各々０．２μｍの電荷発生層、２０
μｍの電荷輸送層、および５μｍの保護層を形成し、本
発明の電子写真感光体を作成した。
〔電荷発生層塗工液〕
下記構造式の電荷発生物質
６部Example 7 A charge generation layer coating solution, a charge transport layer coating solution, and a protective layer coating solution having the following compositions were sequentially coated and dried on an Al cylindrical support having a diameter of 60 mm. .2 μm charge generation layer, 20
A charge transport layer with a thickness of μm and a protective layer with a thickness of 5 μm were formed to produce an electrophotographic photoreceptor of the present invention. [Charge generation layer coating liquid] Charge generation substance with the following structural formula
Part 6
【化４７】
下記構造式の一般式（Ｉ）の化合物
４部embedded image Compound of general formula (I) with the following structural formula
4th part
【化４８】
シクロヘキサノン
４００部 ４−メチル−２−ペンタノン
２００部〔電荷輸送層塗
工液〕
下記構造式の電荷輸送物質
７部[Chemical formula 48] Cyclohexanone
400 parts 4-methyl-2-pentanone
200 parts [Charge transport layer coating liquid] Charge transport substance having the following structural formula
7th part
【化４９】
ポリカーボネート（帝人化成（株）製パンライトＣ
−１４００） １０部 塩
化メチレン
８０部〔保護層塗工液〕
スチレン〜メチルメタクリレート〜２−ヒドロキシ
エチルメタクリレ ート〜トリフロロエチルメタクリ
レート共重合体
７０部 導電性酸化チタン
９０部 トルエン
２
２０部 ｎ−ブタノール
６０部[Chemical formula 49] Polycarbonate (Panlite C manufactured by Teijin Kasei Ltd.)
-1400) 10 parts methylene chloride
80 parts [Protective layer coating liquid] Styrene - methyl methacrylate - 2-hydroxyethyl methacrylate - trifluoroethyl methacrylate copolymer
70 parts conductive titanium oxide
90 parts toluene
2
20 parts n-butanol
60 copies
【００９７】実施例
８
φ８０のＡｌの円筒状支持体上に、下記組成の電荷発生
層塗工液、電荷輸送層塗工液および保護層塗工液を順次
、塗布・乾燥して、各々０．２μｍの電荷発生層、１９
μｍの電荷輸送層及び５μｍの保護層を形成し、本発明
の電子写真感光体を作成した。〔電荷輸送層塗工液〕
下記構造式の電荷輸送物質
５部Example 8 On a φ80 aluminum cylindrical support, a charge generation layer coating solution, a charge transport layer coating solution and a protective layer coating solution having the following compositions were sequentially coated and dried to give a coating composition of 0. .2 μm charge generation layer, 19
A charge transport layer with a thickness of 5 μm and a protective layer with a thickness of 5 μm were formed to prepare an electrophotographic photoreceptor of the present invention. [Charge transport layer coating liquid]
Charge transport material with the following structural formula
5th part
【化５０】
下記構造式の一般式（Ｉ）の化合物
２部embedded image Compound of general formula (I) with the following structural formula
2nd part
【化５１】
ポリビニルブチラール（積水化学工業（株）製エス
レックＢＭ−Ｓ） ２部 トルイレ
ン−２，４−ジイソシアネート
０．１部
シクロヘキサノン
４００部 ２−ブタノン
１００部〔電荷輸送
層塗工液〕
下記構造式の電荷輸送物質
１０部[Chemical formula 51] Polyvinyl butyral (S-LEC BM-S manufactured by Sekisui Chemical Co., Ltd.) 2 parts Toluylene-2,4-diisocyanate
0.1 part
cyclohexanone
400 parts 2-butanone
100 parts [Charge transport layer coating liquid] Charge transport substance having the following structural formula
10 copies
【化５２】
ポリエステル（東洋紡績（株）製バイロン２００）
１０部
テトラヒドロフラン
８０部[Chemical formula 52] Polyester (Byron 200 manufactured by Toyobo Co., Ltd.)
10 parts Tetrahydrofuran
80 copies
【００９８】比較例１〜６
以上の様に作成した実施例１〜６の感光体において、各
々の電荷発生層に一般式（Ｉ）の化合物を含有させない
他はすべて実施例１〜６と同様にして感光体を形成し、
比較例１〜６の感光体とした。以上の各感光体の特性を
、静電複写紙試験装置（川口電機製作所製ＳＰ−４２８
型）を用いて次のように評価した。まず、−５．２ＫＶ
の放電々圧にて、コロナ帯電を２０秒間行ない、次いで
暗減衰させ表面電位が−８００Ｖになったところで、８
ｌｕｘのタングステン光を照射した。この時の帯電開始
後２秒および２０秒の表面電位Ｖ２（Ｖ）、Ｖ２０（Ｖ
）また光照射の際、表面電位が−４００Ｖになるのに必
要な露光量Ｅ４００（ｌｕｘ・ｓｅｃ）を測定した。更
に、この感光体に色温度２８５６°Ｋのタングステン光
を６０００ ｌｕｘ・ｓｅｃ照射して光疲労させた後、
再び前記と同様にしてＶ２、Ｖ２０、Ｖ４００を測定し
た。評価結果を表４に示す。Comparative Examples 1 to 6 The photoreceptors of Examples 1 to 6 prepared as described above were all the same as Examples 1 to 6 except that the compound of general formula (I) was not contained in each charge generation layer. to form a photoreceptor,
Photoreceptors of Comparative Examples 1 to 6 were used. The characteristics of each photoreceptor above were measured using an electrostatic copying paper tester (SP-428 manufactured by Kawaguchi Electric Seisakusho).
It was evaluated as follows using First, -5.2KV
Corona charging was carried out for 20 seconds at a discharge pressure of
lux tungsten light was irradiated. At this time, the surface potentials V2 (V), V20 (V
) Also, during light irradiation, the exposure amount E400 (lux·sec) required for the surface potential to become -400V was measured. Furthermore, after irradiating this photoreceptor with tungsten light with a color temperature of 2856°K for 6000 lux・sec to cause optical fatigue,
V2, V20, and V400 were measured again in the same manner as above. The evaluation results are shown in Table 4.
【００９９】比較例７〜８
以上の様に作成した実施例７〜８の感光体において、各
々の電荷発生層に一般式（Ｉ）の化合物を含有させない
他はすべて実施例７〜８と同様にして感光体を形成し、
比較例７〜８の感光体とした。以上の様に形成された円
筒状電子写真感光体は、特開昭６０−１００１６７号公
報に開示されている測定装置を用いて以下の様に測定し
た。まず、−５．２ＫＶの放電々圧にて、コロナ帯電を
２０秒間行ない、次いで暗減衰させ表面電位が−８００
Ｖになったところで、８ｌｕｘのタングステン光を照射
した。この時の帯電開始後２秒および２０秒の表面電位
Ｖ２（Ｖ）、Ｖ２０（Ｖ）また光照射の際、表面電位が
−４００Ｖになるのに必要な露光量Ｅ４００（ｌｕｘ・
ｓｅｃ）を測定した。更に、この感光体に色温度２８５
６°Ｋのタングステン光を６０００ｌｕｘ・ｓｅｃ照射
して光疲労させた後、再び前記と同様にしてＶ２、Ｖ２
０、Ｖ４００を測定した。評価結果を表４に示す。Comparative Examples 7-8 The photoreceptors of Examples 7-8 prepared as described above were all the same as Examples 7-8 except that the compound of general formula (I) was not contained in each charge generation layer. to form a photoreceptor,
Photoreceptors of Comparative Examples 7 and 8 were used. The cylindrical electrophotographic photoreceptor formed as described above was measured as follows using a measuring device disclosed in Japanese Patent Application Laid-Open No. 60-100167. First, corona charging was performed for 20 seconds at a discharge pressure of -5.2 KV, and then dark decay was performed until the surface potential reached -800.
When the voltage reached V, tungsten light of 8 lux was irradiated. At this time, the surface potentials V2 (V) and V20 (V) for 2 seconds and 20 seconds after the start of charging, and the exposure amount E400 (lux・
sec) was measured. Furthermore, this photoreceptor has a color temperature of 285
After irradiating tungsten light at 6°K for 6000 lux・sec to cause optical fatigue, V2 and V2 were again treated in the same manner as above.
0, V400 was measured. The evaluation results are shown in Table 4.
【０１００】[0100]
【表４】 ※ ８００Ｖ帯電せず測定不可[Table 4] *800V cannot be measured without charging
【０１０１】[0101]
【実施例９】アルミニウムを蒸着したポリエチレンテレ
フタレートフィルム上に、下記組成の電荷発生層塗工液
、電荷輸送層塗工液を順次、塗布、乾燥して各々０．２
μｍ厚の電荷発生層および２２μｍ厚の電荷輸送層を形
成し、本発明の電子写真感光体を作成した。〔電荷発生
層塗工液〕
下記構造式の電荷発生物質
４部[Example 9] On a polyethylene terephthalate film on which aluminum was vapor-deposited, a charge generation layer coating liquid and a charge transport layer coating liquid having the following compositions were sequentially applied and dried to give a 0.2
A charge generation layer with a thickness of μm and a charge transport layer with a thickness of 22 μm were formed to produce an electrophotographic photoreceptor of the present invention. [Charge generation layer coating liquid] Charge generation substance with the following structural formula
4th part
【化５３】
下記構造式の一般式（ＩＩ）の化合物
２部[Image Omitted] Compound of general formula (II) of the following structural formula
2nd part
【化５４】
ポリビニルブチラール樹脂（電気化学工業株）製デ
ンカブチラール ＃４０００−１）
１部 シクロヘ
キサノン
３００部 ２−ブタノン
５０部〔電荷輸送層塗工
液〕[Chemical formula 54] Polyvinyl butyral resin (Denka Butyral #4000-1 manufactured by Denki Kagaku Kogyo Co., Ltd.)
1 part cyclohexanone
300 parts 2-butanone
50 parts [Charge transport layer coating liquid]
【化５５】
下記構造式の電荷輸送物質
８部 ポリカーボネート（帝人化成製パ
ンライトＬ−１２５０） １０
部 テトラヒドロフラン
７０部[Chemical formula 55] Charge transport substance having the following structural formula
8 parts Polycarbonate (Teijin Kasei Panlite L-1250) 10
Part Tetrahydrofuran
70 copies
【０１０２】実施例１０
実施例１と同じ支持体上に、下記組成の下引層塗工液、
電荷発生層塗工液および電荷輸送層塗工液を順次、塗布
、乾燥して各々０．３μｍの下引層、０．２μｍの電荷
発生層および２０μｍの電荷輸送層を形成し、本発明の
電子写真感光体を作成した。
〔下引層塗工液〕
水溶性ポリビニルブチラールの２５％水溶液（積水
化学工業（株）製エスレックＷ−２０１）
５０部 水
１５０部 メタノール
２００部〔
電荷発生層塗工液〕
下記構造式の電荷発生物質
４部Example 10 On the same support as in Example 1, a subbing layer coating solution having the following composition,
A charge generation layer coating solution and a charge transport layer coating solution were sequentially applied and dried to form a subbing layer of 0.3 μm, a charge generation layer of 0.2 μm, and a charge transport layer of 20 μm, respectively. An electrophotographic photoreceptor was created. [Undercoat layer coating liquid] 25% aqueous solution of water-soluble polyvinyl butyral (S-LEC W-201 manufactured by Sekisui Chemical Co., Ltd.)
50 parts water
150 parts methanol
200 copies [
Charge generation layer coating liquid] Charge generation substance with the following structural formula
4th part
【化５６】
下記構造式の一般式（ＩＩ）の化合物
３部embedded image Compound of general formula (II) of the following structural formula
Part 3
【化５７】
シクロヘキサノン
２００部 ２−ブタノン
１５０部〔電荷
輸送層塗工液〕
下記構造式の電荷輸送物質
９部[Chemical formula 57] Cyclohexanone
200 parts 2-butanone
150 parts [Charge transport layer coating liquid] Charge transport substance having the following structural formula
9th part
【化５８】
ポリカーボネート（帝人化成（株）製パンライトＫ
−１３００） １０部 テトラヒドロフラ
ン
８０部
[Chemical formula 58] Polycarbonate (Panlite K manufactured by Teijin Kasei Ltd.)
-1300) 10 parts Tetrahydrofuran
80 copies
【実施例１１】ハステロイ導電層を設けたポリエチレン
テレフタレートフィルム上に、下記組成の下引層塗工液
、電荷発生層塗工液および電荷輸送層塗工液を順次、塗
布、乾燥して、各々２μｍの下引層、０．３μｍの電荷
発生層および１８μｍの電荷輸送層を形成し、本発明の
電子写真感光体を作成した。
〔下引層塗工液〕
二酸化チタン
１０部 ポリエステル（東洋紡
績（株）バイロン２００）
１部 トルイレン−２，４−ジイ
ソシアネート
０．２部 ２−ブタノン
１００部
４−メチル−２−ペンタノン
７０部〔電荷発生層塗工液〕
下記構造式の電荷発生物質
３部[Example 11] On a polyethylene terephthalate film provided with a Hastelloy conductive layer, a subbing layer coating liquid, a charge generation layer coating liquid, and a charge transport layer coating liquid having the following compositions were sequentially applied and dried. A subbing layer of 2 μm, a charge generation layer of 0.3 μm, and a charge transport layer of 18 μm were formed to prepare an electrophotographic photoreceptor of the present invention. [Undercoat layer coating liquid] Titanium dioxide
10 parts Polyester (Toyobo Co., Ltd. Byron 200)
1 part toluylene-2,4-diisocyanate
0.2 parts 2-butanone
100 copies
4-methyl-2-pentanone
70 parts [Charge generation layer coating liquid] Charge generation substance having the following structural formula
Part 3
【化５９】
下記構造式の一般式（ＩＩ）の化合物
０
．５部embedded image Compound of general formula (II) of the following structural formula
0
．． 5th part
【化６０】
ポリビニルブチラール（ＵＣＣ製 ＸＹＨＬ）
０．５部
シクロヘキサノン
１００部 テトラヒドロフラン
１００部〔電荷輸送層塗工
液〕
下記構造式の電荷輸送物質
７部[Chemical formula 60] Polyvinyl butyral (XYHL manufactured by UCC)
0.5 part
cyclohexanone
100 parts tetrahydrofuran
100 parts [Charge transport layer coating liquid] Charge transport substance having the following structural formula
7th part
【化６１】
ポリアリレート（ユニチカ（株）製 Ｕ−１００
） ９部
テトラヒドロフラン
８０部[Chemical formula 61] Polyarylate (Unitika Co., Ltd. U-100)
) Part 9
Tetrahydrofuran
80 copies
【０１０４】[0104]
【実施例１２】厚さ０．２ｍｍのアルミニウム板上に、
下記組成の電荷発生層塗工液および電荷輸送層塗工液を
順次、塗布乾燥して各々０．２μｍの電荷発生層および
１７μｍの電荷輸送層を形成し、本発明の電子写真感光
体を作成した。
〔電荷発生層塗工液〕
下記構造式の電荷発生物質
１０部[Example 12] On an aluminum plate with a thickness of 0.2 mm,
A charge generation layer coating liquid and a charge transport layer coating liquid having the following compositions were sequentially applied and dried to form a charge generation layer of 0.2 μm and a charge transport layer of 17 μm, respectively, to produce an electrophotographic photoreceptor of the present invention. did. [Charge generation layer coating liquid] Charge generation substance with the following structural formula
10 copies
【化６２】
下記構造式の一般式（ＩＩ）の化合物
２部[Image Omitted] Compound of general formula (II) of the following structural formula
2nd part
【化６３】
ポリエステル（東洋紡績（株）製 バイロン３０
０） ４部 テ
トラヒドロフラン
４００部〔電荷輸送層塗工液〕
下記構造式の電荷輸送物質
１０部[Chemical formula 63] Polyester (Byron 30 manufactured by Toyobo Co., Ltd.)
0) 4 parts Tetrahydrofuran
400 parts [Charge transport layer coating liquid] Charge transport substance having the following structural formula
10 copies
【化６４】
ポリカーボネート（ＧＥ社製 レキサン−１４１
） １０部 塩
化メチレン
９０部[Chemical 64] Polycarbonate (Lexan-141 manufactured by GE)
) 10 parts methylene chloride
90 copies
【０１０５】[0105]
【実施例１３】厚さ０．１ｍｍの電鋳ニッケル板上に、
下記組成の下引層塗工液、電荷発生層塗工液、電荷輸送
層塗工液および保護層塗工液を順次、塗布、乾燥して各
々０．３μｍの下引層、０．２μｍの電荷発生層および
１８μｍの電荷輸送層および３μｍの保護層を形成し、
本発明の電子写真感光体を作成した。
〔下引層塗工液〕
ポリビニルアルコール（電気化学工業（株）製デン
カポバールＨ−２０）２部 水
１００部 メタノール
１００部〔電荷発生層塗工
液〕
下記構造式の電荷発生物質
５部[Example 13] On an electroformed nickel plate with a thickness of 0.1 mm,
A subbing layer coating liquid, a charge generation layer coating liquid, a charge transport layer coating liquid, and a protective layer coating liquid having the following compositions were sequentially applied and dried to form a subbing layer of 0.3 μm and a layer of 0.2 μm. forming a charge generation layer, a charge transport layer of 18 μm and a protective layer of 3 μm;
An electrophotographic photoreceptor of the present invention was prepared. [Undercoat layer coating liquid] 2 parts of polyvinyl alcohol (Denka Poval H-20 manufactured by Denki Kagaku Kogyo Co., Ltd.) Water
100 parts methanol
100 parts [Charge generation layer coating liquid] Charge generation substance having the following structural formula
5th part
【００６５】
下記構造式の一般式（ＩＩ）の化合物
２部Compounds of general formula (II) of the following structural formula
2nd part
【００６６】
ポリサルホン（日産化学（株）製 Ｐ−１７００
） １部
シクロヘキサノン
２００部 テトラヒドロフラン
１３０部〔電荷輸送層
塗工液〕
下記構造式の電荷輸送物質
９部Polysulfone (P-1700 manufactured by Nissan Chemical Co., Ltd.)
) 1 part cyclohexanone
200 parts tetrahydrofuran
130 parts [Charge transport layer coating liquid] Charge transport substance having the following structural formula
9th part
【化６７】
ポリカーボネート（帝人化学（株）製 パンライ
トＫ−１３００） １１部 塩化メチレン
８０部〔保護層塗工液〕
スチレン〜メチルメタクリレート〜３−メタクリロ
キシプロピルトリメトキシシラン共重合体
８０部 酸化錫
８０部 トルエ
ン
１７０部 ２−ブタノン
１００部[Chemical formula 67] Polycarbonate (Teijin Chemical Co., Ltd. Panlite K-1300) 11 parts Methylene chloride
80 parts [Protective layer coating liquid] Styrene-methyl methacrylate-3-methacryloxypropyltrimethoxysilane copolymer
80 parts tin oxide
80 parts toluene
170 parts 2-butanone
100 copies
【０１０
６】010
6]
【実施例１４】実施例１２と同じ支持体上に、下記組成
の下引層塗工液、電荷発生層塗工液および電荷輸送層塗
工液を順次、塗布、乾燥して各々２μｍの下引層、０．
４μｍの電荷発生層および２２μｍの電荷輸送層を形成
し、本発明の電子写真感光体を作成した。
〔下引層塗工液〕
二酸化チタン
８部 ポリビニルブチラー
ル（積水化学工業（株）製エスレックＢＬ−１） １
０部 ２−ブタノン
６０部 酢酸エチル
４０部〔電荷発生層塗工液〕[Example 14] On the same support as in Example 12, a subbing layer coating liquid, a charge generation layer coating liquid, and a charge transport layer coating liquid having the following compositions were sequentially coated and dried, each having a thickness of 2 μm. Attraction layer, 0.
A charge generation layer of 4 μm and a charge transport layer of 22 μm were formed to produce an electrophotographic photoreceptor of the present invention. [Undercoat layer coating liquid] Titanium dioxide
8 parts Polyvinyl butyral (S-LEC BL-1 manufactured by Sekisui Chemical Co., Ltd.) 1
0 parts 2-butanone
60 parts ethyl acetate
40 parts [Charge generation layer coating liquid]
【化６８】
下記構造式の電荷発生物質
５部 下記構造式の一般式（ＩＩ）の化
合物
０．５部[Chemical formula 68] Charge generating substance having the following structural formula
Part 5 Compound of general formula (II) of the following structural formula
0.5 part
【化６９】
ポリエステル（東洋紡績（株）製 バイロン２０
０） ２部 ト
ルイレン−２，４−ジイソシアネート
０．１部 テ
トラヒドロフラン
２００部 ４−メチル−２−ペンタノン
３００部〔電荷輸送層塗工液〕
下記構造式の電荷輸送物質
１０部[Chemical 69] Polyester (Byron 20 manufactured by Toyobo Co., Ltd.)
0) 2 parts toluylene-2,4-diisocyanate
0.1 part tetrahydrofuran
200 parts 4-methyl-2-pentanone
300 parts [Charge transport layer coating liquid] Charge transport substance having the following structural formula
10 copies
【化７０】
ポリカーボネート（三菱瓦斯化学（株）製ポリカー
ボネートＺ） １０部 塩化メチレン
５０部 １，２−ジクロロエタン
２５部[Chemical formula 70] Polycarbonate (Polycarbonate Z manufactured by Mitsubishi Gas Chemical Co., Ltd.) 10 parts Methylene chloride
50 parts 1,2-dichloroethane
25 copies
【０１０７】[0107]
【実施例１５】φ６０ｍｍのＡｌ円筒状支持体上に、下
記組成の電荷発生層塗工液、電荷輸送層塗工液、および
保護層塗工液を順次、塗布、乾燥して、各々０．２μｍ
の電荷発生層、２０μｍの電荷輸送層、および５μｍの
保護層を形成し、本発明の電子写真感光体を作成した。
〔電荷発生層塗工液〕
下記構造式の電荷発生物質
３部Example 15 On an Al cylindrical support with a diameter of 60 mm, a charge generation layer coating solution, a charge transport layer coating solution, and a protective layer coating solution having the following compositions were sequentially coated and dried. 2μm
A charge generation layer of 20 μm, a charge transport layer of 20 μm, and a protective layer of 5 μm were formed to prepare an electrophotographic photoreceptor of the present invention. [Charge generation layer coating liquid] Charge generation substance with the following structural formula
Part 3
【化７１】
下記構造式の一般式（ＩＩ）の化合物
１部embedded image Compound of general formula (II) of the following structural formula
Part 1
【化７２】
シクロヘキサノン
１００部 ４−メチル−２−ペンタノン
７０部〔電荷輸送層塗工液
〕
下記構造式の電荷輸送物質
９部[Chemical formula 72] Cyclohexanone
100 parts 4-methyl-2-pentanone
70 parts [Charge transport layer coating liquid] Charge transport substance having the following structural formula
9th part
【化７３】
ポリカーボネート（帝人化成（株）製パンライトＣ
−１４００） １０部 塩化メチレン
７０部〔保護層塗工液〕
スチレン〜メチルメタクリレート〜２−ヒドロキシ
エチルメチクリレート〜トリフロロエチルメタクリレー
ト共重合体 ７０部 導電性
酸化チタン
９０部 トルエン
２２０部 ｎ−ブ
タノール
６０部[Chemical formula 73] Polycarbonate (Panlite C manufactured by Teijin Kasei Ltd.)
-1400) 10 parts methylene chloride
70 parts [Protective layer coating liquid] Styrene - methyl methacrylate - 2-hydroxyethyl methacrylate - trifluoroethyl methacrylate copolymer 70 parts Conductive titanium oxide
90 parts toluene
220 parts n-butanol
60 copies
【０１０８】実施例１６
φ８０ｍｍのＡｌ円筒状支持体上に、下記組成の電荷発
生層塗工液、電荷輸送層塗工液、および保護層塗工液を
順次、塗布、乾燥して、各々０．２μｍの電荷発生層及
び１９μｍの電荷輸送層を形成し、本発明の電子写真感
光体を作成した。
〔電荷発生層塗工液〕
下記構造式の電荷発生物質
４部Example 16 A charge generation layer coating solution, a charge transport layer coating solution, and a protective layer coating solution having the following compositions were sequentially coated and dried on an Al cylindrical support having a diameter of 80 mm. A charge generation layer of .2 μm and a charge transport layer of 19 μm were formed to prepare an electrophotographic photoreceptor of the present invention. [Charge generation layer coating liquid] Charge generation substance with the following structural formula
4th part
【化７４】
下記構造式の一般式（ＩＩ）の化合物
３部embedded image Compound of general formula (II) of the following structural formula
Part 3
【化７５】
ポリビニルブチラール（積水化学工業（株）製エス
レックＢＭ−Ｓ） ２部 トルイレン−２，４
−ジイソシアネート
０．１部 シクロヘキサノン
４００部
２−ブタノン
１００部〔電荷輸送層塗工液〕
下記構造式の電荷輸送物質
８部[Chemical formula 75] Polyvinyl butyral (S-LEC BM-S manufactured by Sekisui Chemical Co., Ltd.) 2 parts Toluylene-2,4
-Diisocyanate
0.1 part cyclohexanone
400 copies
2-butanone
100 parts [Charge transport layer coating liquid] Charge transport substance having the following structural formula
Part 8
【化７６】
ポリエステル（東洋紡績（株）製 バイロン２０
０） １０部 テト
ラヒドロフラン
７０部[Chemical formula 76] Polyester (Byron 20 manufactured by Toyobo Co., Ltd.)
0) 10 parts Tetrahydrofuran
70 copies
【０１０９】
比較例９〜１４
以上の様に作成した実施例９〜１４の感光体において、
各々の電荷発生層に一般式（ＩＩ）の化合物を含有させ
ない他はすべて実施例９〜１４と同様にして感光体を形
成し、比較例９〜１４の感光体とした。 以上の各感
光体の特性を、静電複写紙試験装置（川口電機製作所製
ＳＰ−４２８型）を用いて次のように評価した。まず、
−５．５ＫＶの放電々圧にて、コロナ帯電を１５秒間行
ない、次いで１５秒間暗減衰させ、その後、６ｌｕｘの
タングステン光を照射した。この時の帯電開始後１秒と
１５秒の表面電位Ｖ１（Ｖ）、Ｖ１５（Ｖ）および暗減
衰１５秒後の表面電位Ｖ３０（Ｖ）を測定し、また、Ｖ
３０を半分の電位に光減衰させるのに必要な露光量Ｅ１
／２（ｌｕｘ・ｓｅｃ）を測定した。なお、暗減衰率（
Ｄ．Ｄ）は、次式で定義される。
Ｄ．Ｄ＝Ｖ３０／Ｖ１５
更に、上記条件の帯電と露光を同時に３０分間行な
って疲労させた後、再び前記と同様の測定を行なった。
評価結果を表−１に示す。比較例１５〜１６以上の様に
作成した実施例１５〜１６の感光体において、各々の電
荷発生層に一般式（ＩＩ）の化合物を含有させない他は
すべて実施例１５〜１６と同様にして感光体を形成し、
比較例１５〜１６の感光体とした。以上の様に形成され
た円筒状電子写真感光体は、特開昭６０−１００１６７
号公報に開示されている測定装置を用いて以下の様に測
定した。まず、−５．５ＫＶの放電々圧にて、コロナ帯
電を１５秒間行ない、次いで１５秒間暗減衰させ、その
後、５ｌｕｘのタングステン光を照射した。この時の帯
電開始後１秒と１５秒の表面電位Ｖ１５（Ｖ）、Ｖ３０
（Ｖ）および暗減衰１５秒後の表面電位Ｖ３０（Ｖ）を
測定し、また、Ｖ３０を半分の電位に光減衰させるのに
必要な露光量Ｅ１／２（ｌｕｘ・ｓｅｃ）を測定した。
なお、暗減衰率（Ｄ．Ｄ）は、次式で定義される。
Ｄ．Ｄ＝Ｖ３０／Ｖ１５
更に、上記条件の帯電と露光を同時に３０分間行な
って疲労させた後、再び前記と同様の測定を行なった。
評価結果を表５に示す。Comparative Examples 9 to 14 In the photoreceptors of Examples 9 to 14 prepared as above,
Photoreceptors were formed in the same manner as in Examples 9 to 14, except that each charge generation layer did not contain the compound of general formula (II), and were used as photoreceptors of Comparative Examples 9 to 14. The characteristics of each of the photoreceptors described above were evaluated as follows using an electrostatic copying paper tester (model SP-428 manufactured by Kawaguchi Electric Seisakusho). first,
Corona charging was performed for 15 seconds at a discharge voltage of -5.5 KV, followed by dark decay for 15 seconds, and then tungsten light of 6 lux was irradiated. At this time, the surface potentials V1 (V) and V15 (V) at 1 second and 15 seconds after the start of charging, and the surface potential V30 (V) after 15 seconds of dark decay were measured, and the V
Exposure amount E1 required to optically attenuate 30 to half the potential
/2 (lux·sec) was measured. Note that the dark decay rate (
D. D) is defined by the following equation. D. D=V30/V15 Further, charging and exposure under the above conditions were performed simultaneously for 30 minutes to cause fatigue, and then the same measurements as above were performed again. The evaluation results are shown in Table-1. Comparative Examples 15 and 16 The photoreceptors of Examples 15 and 16 prepared as described above were photosensitive in the same manner as in Examples 15 and 16, except that the compound of general formula (II) was not contained in each charge generation layer. form the body,
Photoreceptors of Comparative Examples 15 and 16 were used. The cylindrical electrophotographic photoreceptor formed as described above is disclosed in Japanese Patent Application Laid-Open No. 60-100167.
The measurement was carried out as follows using the measuring device disclosed in the publication. First, corona charging was performed for 15 seconds at a discharge pressure of -5.5 KV, followed by dark decay for 15 seconds, and then 5 lux tungsten light was irradiated. Surface potentials V15 (V) and V30 at 1 second and 15 seconds after the start of charging at this time
(V) and the surface potential V30 (V) after 15 seconds of dark decay, and the exposure amount E1/2 (lux·sec) required to photoattenuate V30 to half the potential was measured. Note that the dark decay rate (D.D) is defined by the following equation. D. D=V30/V15 Further, charging and exposure under the above conditions were performed simultaneously for 30 minutes to cause fatigue, and then the same measurements as above were performed again. The evaluation results are shown in Table 5.
【０１１０】[0110]
【表５−（１）】[Table 5-(1)]
【０１１１】[0111]
【表５−（２）】 ※ Ｖ３０の値が小さく測定不可[Table 5-(2)] *V30 value is too small to measure
【０１１２】[0112]
【発明の効果】本発明によれば、高感度を有する積層型
有機電子感写感光体のくり返し使用後の帯電電位の立上
りの遅れを防ぐことが可能となる。すなわち、複写機、
プリンター等の画像濃度低下画像濃度ムラ、カブリ、あ
るいは反転現像時においては地肌汚れのない良好な画像
を得ることができる。According to the present invention, it is possible to prevent a delay in the rise of the charged potential after repeated use of a laminated organic electrophotosensitive member having high sensitivity. That is, a copying machine,
Good images without background stains can be obtained when image density is reduced, uneven image density, fog, or during reverse development in a printer or the like.
【図１】本発明に係る代表的な電子写真感光体の模式断
面図である。FIG. 1 is a schematic cross-sectional view of a typical electrophotographic photoreceptor according to the present invention.
【図２】導電性支持体と電荷発生層との間に下引層を設
けた本発明の電子写真感光体の模式断面図である。FIG. 2 is a schematic cross-sectional view of an electrophotographic photoreceptor of the present invention in which a subbing layer is provided between a conductive support and a charge generation layer.
【図３】電荷輸送層の上に保護層を設けた本発明の電子
写真感光体の模式断面図である。FIG. 3 is a schematic cross-sectional view of an electrophotographic photoreceptor of the present invention in which a protective layer is provided on a charge transport layer.
【図４】下引層と保護層の両者を備えた本発明の電子写
真感光体の模式断面図である。FIG. 4 is a schematic cross-sectional view of an electrophotographic photoreceptor of the present invention including both an undercoat layer and a protective layer.
Claims (2)
層と電荷輸送層を順次積層してなる電子写真感光体にお
いて、該電荷発生層中に下記一般式化１で示される化合
物を含有してなることを特徴とする電子写真感光体。 【化１】 〔式中、Ａは９−アントリル基、置換又は無置換のＮ−
置換カルバゾリル基、Ｎ−置換フェノチアジニル基又は
−Ａｒ−Ｎ（Ｒ１）（Ｒ２）（式中Ａｒは置換又は無置
換のアリーレン基を表わし、Ｒ１及びＲ２は置換又は無
置換のアルキル基、置換又は無置換のアラルキル基、置
換又は無置換のアリール基を表わす）を表わし、Ｒは水
素原子、置換又は無置換のアルキル基、置換又は無置換
のアラルキル基又は置換又は無置換のアリール基を表わ
す。ｎは０〜８の整数を表わす。〕1. An electrophotographic photoreceptor comprising at least a charge generation layer and a charge transport layer sequentially laminated on a conductive support, wherein the charge generation layer contains a compound represented by the following general formula 1. An electrophotographic photoreceptor characterized by: [Formula, A is a 9-anthryl group, substituted or unsubstituted N-
Substituted carbazolyl group, N-substituted phenothiazinyl group or -Ar-N(R1)(R2) (wherein Ar represents a substituted or unsubstituted arylene group, R1 and R2 are substituted or unsubstituted alkyl groups, substituted or R represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aryl group. n represents an integer from 0 to 8. ]
層と電荷輸送層を順次積層中に下記一般式化２で示され
る化合物を含有してなることを特徴とする電子写真感光
体。 【化２】 〔式中、Ａは９−アントリル基、置換又は無置換のＮ−
置換カルバゾリル基、Ｎ−置換フェノチアジニル基又は
−Ａｒ−Ｎ（Ｒ１）（Ｒ２）（式中Ａｒは置換又は無置
換のアリーレン基を表わし、Ｒ１及びＲ２は置換又は無
置換のアルキル基、置換又は無置換のアラルキル基、置
換又は無置換のアリール基を表わす）を表わし、Ｒは水
素原子、置換又は無置換のアルキル基、置換又は無置換
のアラルキル基又は置換又は無置換のアリル基を表わす
。ｍは２〜８の整数を表わす。ｎは０又は１の整数を表
わす。〕2. An electrophotographic photoreceptor characterized in that at least a charge generation layer and a charge transport layer are sequentially laminated on a conductive support and a compound represented by the following general formula 2 is contained therein. [In the formula, A is a 9-anthryl group, substituted or unsubstituted N-
Substituted carbazolyl group, N-substituted phenothiazinyl group or -Ar-N(R1)(R2) (wherein Ar represents a substituted or unsubstituted arylene group, R1 and R2 are substituted or unsubstituted alkyl groups, substituted or R represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted allyl group. m represents an integer from 2 to 8. n represents an integer of 0 or 1. ]
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2-243091 | 1990-09-13 | ||
| JP24309190 | 1990-09-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH04212165A true JPH04212165A (en) | 1992-08-03 |
Family
ID=17098656
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3373391A Pending JPH04212165A (en) | 1990-09-13 | 1991-02-01 | Electrophotographic sensitive body |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH04212165A (en) |
-
1991
- 1991-02-01 JP JP3373391A patent/JPH04212165A/en active Pending
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