JPH04146446A - Electrophotographic sensitive body - Google Patents
Electrophotographic sensitive bodyInfo
- Publication number
- JPH04146446A JPH04146446A JP27007890A JP27007890A JPH04146446A JP H04146446 A JPH04146446 A JP H04146446A JP 27007890 A JP27007890 A JP 27007890A JP 27007890 A JP27007890 A JP 27007890A JP H04146446 A JPH04146446 A JP H04146446A
- Authority
- JP
- Japan
- Prior art keywords
- group
- carrier
- groups
- layer
- photoreceptor
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- -1 azo compound Chemical class 0.000 claims abstract description 82
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 12
- 108091008695 photoreceptors Proteins 0.000 claims description 50
- 239000000126 substance Substances 0.000 claims description 48
- 125000001424 substituent group Chemical group 0.000 claims description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 5
- 150000004945 aromatic hydrocarbons Chemical class 0.000 abstract description 5
- 239000000463 material Substances 0.000 abstract description 5
- 229930195733 hydrocarbon Natural products 0.000 abstract description 2
- 150000002430 hydrocarbons Chemical class 0.000 abstract description 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- 238000010030 laminating Methods 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 57
- 150000001875 compounds Chemical class 0.000 description 25
- 125000000217 alkyl group Chemical group 0.000 description 17
- 125000000623 heterocyclic group Chemical group 0.000 description 17
- 125000003118 aryl group Chemical group 0.000 description 16
- 229920005989 resin Polymers 0.000 description 14
- 239000011347 resin Substances 0.000 description 14
- 230000035945 sensitivity Effects 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- 125000003277 amino group Chemical group 0.000 description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 9
- 125000003545 alkoxy group Chemical group 0.000 description 8
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 7
- 239000011230 binding agent Substances 0.000 description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 7
- 125000005843 halogen group Chemical group 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 6
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 6
- 125000004104 aryloxy group Chemical group 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 6
- 125000002252 acyl group Chemical group 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 239000003963 antioxidant agent Substances 0.000 description 5
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 239000002612 dispersion medium Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 5
- 229920005668 polycarbonate resin Polymers 0.000 description 5
- 239000004431 polycarbonate resin Substances 0.000 description 5
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 4
- 239000002356 single layer Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000004423 acyloxy group Chemical group 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 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
- 238000006243 chemical reaction Methods 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 3
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 3
- 239000011241 protective layer Substances 0.000 description 3
- 229910052711 selenium Inorganic materials 0.000 description 3
- 239000011669 selenium Substances 0.000 description 3
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 3
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- WUPHOULIZUERAE-UHFFFAOYSA-N 3-(oxolan-2-yl)propanoic acid Chemical compound OC(=O)CCC1CCCO1 WUPHOULIZUERAE-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000004419 Panlite Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052980 cadmium sulfide Inorganic materials 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 239000002800 charge carrier Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-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
- 239000000975 dye Substances 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 239000002985 plastic film Substances 0.000 description 2
- 229920006255 plastic film Polymers 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 229910052727 yttrium Inorganic materials 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
- WPMHMYHJGDAHKX-UHFFFAOYSA-N 1-ethenylpyrene Chemical compound C1=C2C(C=C)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 WPMHMYHJGDAHKX-UHFFFAOYSA-N 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- MYKQKWIPLZEVOW-UHFFFAOYSA-N 11h-benzo[a]carbazole Chemical group C1=CC2=CC=CC=C2C2=C1C1=CC=CC=C1N2 MYKQKWIPLZEVOW-UHFFFAOYSA-N 0.000 description 1
- BIEFDNUEROKZRA-UHFFFAOYSA-N 2-(2-phenylethenyl)aniline Chemical class NC1=CC=CC=C1C=CC1=CC=CC=C1 BIEFDNUEROKZRA-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- JHUUPUMBZGWODW-UHFFFAOYSA-N 3,6-dihydro-1,2-dioxine Chemical compound C1OOCC=C1 JHUUPUMBZGWODW-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
- OGOYZCQQQFAGRI-UHFFFAOYSA-N 9-ethenylanthracene Chemical compound C1=CC=C2C(C=C)=C(C=CC=C3)C3=CC2=C1 OGOYZCQQQFAGRI-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 125000000641 acridinyl group Chemical class C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000005577 anthracene group Chemical group 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 1
- 229940027998 antiseptic and disinfectant acridine derivative Drugs 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- HXTLWOZJMYIANK-UHFFFAOYSA-N butyl acetate;methanol Chemical compound OC.CCCCOC(C)=O HXTLWOZJMYIANK-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 description 1
- 229920006026 co-polymeric resin Polymers 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 125000000332 coumarinyl group Chemical group O1C(=O)C(=CC2=CC=CC=C12)* 0.000 description 1
- 150000001907 coumarones Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000006866 deterioration 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
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- LJJQENSFXLXPIV-UHFFFAOYSA-N fluorenylidene Chemical group C1=CC=C2[C]C3=CC=CC=C3C2=C1 LJJQENSFXLXPIV-UHFFFAOYSA-N 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000000687 hydroquinonyl group Chemical class C1(O)=C(C=C(O)C=C1)* 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 150000002461 imidazolidines Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 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
- 125000001041 indolyl group Chemical group 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 229940102253 isopropanolamine Drugs 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000113 methacrylic resin Substances 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
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Landscapes
- Photoreceptors In Electrophotography (AREA)
Abstract
Description
【発明の詳細な説明】
[産業上の利用分野]
本発明は電子写真感光体に関し、詳しくはビスアゾ化合
物を含有する感光層を有する電子写真感光体に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to an electrophotographic photoreceptor, and more particularly to an electrophotographic photoreceptor having a photosensitive layer containing a bisazo compound.
[従来の技術]
従来、電子写真感光体としては、セレン、酸化亜鉛、硫
化カドミウム、シリコン等の無機光導電性化合物を主成
分とする感光層を有する無機感光体が、広く用いられて
きた。しかし、これらは感度、熱安定性、耐湿性、耐久
性等において必ずしも満足し得るものではない。例えば
、セレンは結晶化すると感光体としての特性が劣化して
しまうため製造上も難しく、また熱や指紋等が原因とな
り結晶化し、感光体としての性能が劣化してしまう。ま
た硫化カドミウムでは耐湿性や耐久性について、酸化亜
鉛では耐久性等に問題がある。[Prior Art] Conventionally, inorganic photoreceptors having a photosensitive layer containing an inorganic photoconductive compound such as selenium, zinc oxide, cadmium sulfide, or silicon as a main component have been widely used as electrophotographic photoreceptors. However, these are not necessarily satisfactory in terms of sensitivity, thermal stability, moisture resistance, durability, etc. For example, when selenium crystallizes, its properties as a photoreceptor deteriorate, making it difficult to manufacture.Also, selenium crystallizes due to heat, fingerprints, etc., and its performance as a photoreceptor deteriorates. Furthermore, cadmium sulfide has problems with moisture resistance and durability, while zinc oxide has problems with durability.
これら無機感光体の持つ欠点を克服する目的で様々な有
機光導電性化合物を主成分とする感光層を有する有機感
光体の研究・開発が近年盛んに行われている。例えば特
公昭50−10496号にはポリ−N−ビニルカルバゾ
ールと2.4.7−)ジニトロ−9−フルオレノンを含
有する感光層を有する有機感光体の記載がある。しかし
この感光体は、感度及び耐久性においてかならずしも満
足できるものではない。このためキャリア発生機能とキ
ャリア輸送機能とを異なる物質にそれぞれ分担させ、よ
り高性能の有機感光体を開発する試みがなされている。In order to overcome these drawbacks of inorganic photoreceptors, research and development of organic photoreceptors having photosensitive layers mainly composed of various organic photoconductive compounds has been actively conducted in recent years. For example, Japanese Patent Publication No. 50-10496 describes an organic photoreceptor having a photosensitive layer containing poly-N-vinylcarbazole and 2,4,7-)dinitro-9-fluorenone. However, this photoreceptor is not always satisfactory in terms of sensitivity and durability. For this reason, attempts have been made to develop organic photoreceptors with higher performance by assigning the carrier generation function and the carrier transport function to different substances, respectively.
このようないわゆる機能分離型の感光体の形態としては
単層型と積層型の2種類があり、両者ともそれぞれの材
料を広い範囲から選択することができ、任意の性能を有
する感光体を比較的容易に作成し得ることから多くの研
究がなされてきた。このような機能分離型感光体におい
てキャリア発生機能を有するキャリア発生物質として、
有機染料や有機顔料等数多くの化合物が提案されている
。例えば特開昭54−22834号、同55−7305
7号、同55−117151号、同56−46237号
等にはアゾ化合物、とりわけビスアゾ化合物を感光層中
に含有する電子写真感光体についての記載がある。There are two types of so-called function-separated type photoreceptors: single-layer type and laminated type.For both, materials can be selected from a wide range, and photoreceptors with arbitrary performance can be compared. A lot of research has been done on it because it is easy to create. As a carrier generating substance having a carrier generating function in such a functionally separated photoreceptor,
Many compounds such as organic dyes and organic pigments have been proposed. For example, JP-A-54-22834, JP-A-55-7305
No. 7, No. 55-117151, No. 56-46237, etc., describe electrophotographic photoreceptors containing an azo compound, particularly a bisazo compound, in the photosensitive layer.
[発明が解決しようとする課題]
しかし上記各公報記載のビスアゾ化合物はいずれも感度
、残留電位あるいは、繰返し使用時の安定性の特性にお
いて、必ずしも満足し得るものではなく、また、キャリ
ア輸送物質の選択範囲も限定されるなど、電子写真プロ
セスの幅広い要求を十分満足させるものではない。[Problems to be Solved by the Invention] However, the bisazo compounds described in the above publications are not necessarily satisfactory in terms of sensitivity, residual potential, or stability during repeated use. The selection range is also limited, and the wide range of demands of electrophotographic processes cannot be fully satisfied.
本発明は上記問題点を解決すべくなされたものであり、
本発明の目的はキャリア発生能に優れた特定のビスアゾ
化合物を有する電子写真感光体を提供することにある。The present invention has been made to solve the above problems,
An object of the present invention is to provide an electrophotographic photoreceptor containing a specific bisazo compound having excellent carrier generation ability.
本発明の他の目的は、高感度でかつ残留電位が小さく、
更に繰り返し使用してもそれらの特性が変化しない耐久
性の優れた電子写真感光体を提供することにある。Another object of the present invention is to provide high sensitivity and low residual potential.
Furthermore, it is an object of the present invention to provide an electrophotographic photoreceptor with excellent durability whose properties do not change even after repeated use.
本発明の更に他の目的は、広範なキャリア輸送物質との
組合せにおいても、キャリア発生物質として有効に作用
し得るビスアゾ化合物を含有する電子写真感光体を提供
することにある。Still another object of the present invention is to provide an electrophotographic photoreceptor containing a bisazo compound that can effectively act as a carrier generating substance even in combination with a wide variety of carrier transporting substances.
1課題を解決するための手段]
本発明者等は、以上の目的を達成すべく鋭意研究を重ね
た結果、特定のビスアゾ化合物が電子写真感光体の優れ
た有効成分として働き得る事を見いだし、本発明を完成
したものである。すなわち、本発明の上記目的は、導電
性支持体上に下記一般式[I]で示されるビスアゾ化合
物を含有する感光層を有することを特徴とする電子写真
感光体によって達成される。Means for Solving 1 Problem] As a result of intensive research to achieve the above object, the present inventors have discovered that a specific bisazo compound can act as an excellent active ingredient of an electrophotographic photoreceptor, This completes the present invention. That is, the above object of the present invention is achieved by an electrophotographic photoreceptor characterized by having a photosensitive layer containing a bisazo compound represented by the following general formula [I] on a conductive support.
一般式[I]
[式中Cpはそれぞれ独立にフェノール性水酸基を有す
るカプラー残基を表わし、R1,R’R8R4及びR1
′はそれぞれ置換基を表わし、ml及びmBはそれぞれ
O〜5の整数を表わし、m2及びm4はそれぞれO〜4
の整数を表わし、m3はO〜3の整数を表わし、り及び
nはそれぞれO又は1を表わす。]
以下本発明を更に詳しく説明する。General formula [I] [In the formula, Cp each independently represents a coupler residue having a phenolic hydroxyl group, R1, R'R8R4 and R1
′ each represents a substituent, ml and mB each represent an integer of O to 5, m2 and m4 each represent an integer of O to 4
m3 represents an integer from O to 3, and ri and n each represent O or 1. ] The present invention will be explained in more detail below.
一般式[I]中−N=N−Cpは2個含有され、R1,
R2,R”、R’又はR5が置換されうる位置のどこに
でも結合することができる。但し−N二N−Cpの置換
位置によりm”、m2.m”、m’。In the general formula [I], two -N=N-Cp are contained, R1,
It can be bonded to any position where R2, R", R' or R5 can be substituted. However, depending on the position of substitution of -N2N-Cp, m", m2. m", m'.
mBの値は適宜変化するものとする。式中2個のCpは
同じでも異なっていてもよい。また本発明においてはm
11m21m31m4及びm6の値がそれぞれ2以上の
時、m1個のR1、m2個のR2m3個のR3、m4個
のR4及びm6個のR5はそれぞれ同じでも異なってい
てもよい。It is assumed that the value of mB changes as appropriate. Two Cp's in the formula may be the same or different. Furthermore, in the present invention, m
When the values of 11m21m31m4 and m6 are each 2 or more, m1 R1, m2 R2, m3 R3, m4 R4, and m6 R5 may be the same or different.
Cpはフェノール性水酸基を有するカプラー残基を表わ
すが、ここでいうフェノール性水酸基とは、芳香族炭化
水素環に置換した水酸基のことであり、この芳香族炭化
水素環にさらに、炭化水素環あるいは複素環が縮合して
いてもよい。Cp represents a coupler residue having a phenolic hydroxyl group, and the phenolic hydroxyl group here refers to a hydroxyl group substituted on an aromatic hydrocarbon ring. The heterocycles may be fused.
具体的には下記一般式[n]〜[XI]されるカプラー
残基が挙げられる。Specifically, coupler residues represented by the following general formulas [n] to [XI] can be mentioned.
一般式[n]
で表わ
(式中、Y、およびY、は、それぞれ独立に水素原子、
ハロゲン原子、アルキル基、アリール基、複素環基、ア
ルコキシ基、アリールオキシ基、アラルキルオキシ基、
カルボキシル基、アルコキシカルボニル基、アリールオ
キシカルボニル基、カルバモイル基、ヒドラジノカルボ
ニル基、アシル基又はアシルアミノ基を示す。)
一般式[I11]
(式中、
Y8は、
それぞれ独立に水素原子、
ロゲン原子、アルキル基、アリール基、複素環基、アル
コキシ基、アリールオキシ基、アラルキルオキシ基、カ
ルボキシル基、アルコキシカルボニル基、アリールオキ
シカルボニル基またはアシル基を示し、2はベンゼン環
と縮合して、芳香族炭化水素環または複素環を形成する
ための2価の基を示す。)
一般式[rV]
(式中R□およびR3は、それぞれ水素原子、低級アル
キル基、アリール基または複素環基を示し、R□とR7
は互いに結合して環を形成していてもよい。Zは前記一
般式[mlにおけるものと同義である。)
一般式
[]
(式中、R□、 R2およびZは、それぞれ前記−般式
[TV]におけるものと同義である。)一般式[VI]
(式中、R8およびR4は、それぞれ水素原子、アルキ
ル基、不飽和アルキル基、アリール基、複素環基、ビニ
ル基、またはブタジェニル基を示し、R3とR1は互い
に結合して環を形成していてもよい。Zは前記一般式[
I[[]におけるものと同義である。)
一般式
[]
(式中、R工およびR3は、それぞれ前記一般式[T’
/]又は一般式[VI]におけるものと同義である。)
一般式[■]
(式中、R4およびZは、前記一般式
は[rV]におけるものと同義である。)一般式[IX
] Rs
[I[I]
又
(式中、R,は、アルキル基もしくは不飽和アルキル基
またはアリール基を示す。)
一般式[X]
[式中R,,R,,R1およびR8は、それぞれ水素原
子、ハロゲン原子、アルキル基、ビニル基、置換アミノ
基またはアリール基を表わし、R6はこの他に、−CR
LO(但しRo。は、アルキル基、I
アリール基、複素環基、ビニル基、アミノ基またはアシ
ロキシ基を示す。)を示す。]
一般般式XIコ
(式中Qは2価の芳香族炭化水素基、
または2
価の複素環基を示す。)
但し上記一般式[I1]〜[XI]中の多基は置換基を
有していてもよい。Represented by the general formula [n] (wherein, Y and Y are each independently a hydrogen atom,
Halogen atom, alkyl group, aryl group, heterocyclic group, alkoxy group, aryloxy group, aralkyloxy group,
It represents a carboxyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a carbamoyl group, a hydrazinocarbonyl group, an acyl group, or an acylamino group. ) General formula [I11] (wherein Y8 is each independently a hydrogen atom, a rogene atom, an alkyl group, an aryl group, a heterocyclic group, an alkoxy group, an aryloxy group, an aralkyloxy group, a carboxyl group, an alkoxycarbonyl group, Represents an aryloxycarbonyl group or an acyl group, and 2 represents a divalent group for condensing with a benzene ring to form an aromatic hydrocarbon ring or a heterocycle.) General formula [rV] (In the formula, R□ and R3 each represent a hydrogen atom, a lower alkyl group, an aryl group, or a heterocyclic group, and R□ and R7
may be bonded to each other to form a ring. Z has the same meaning as in the general formula [ml]. ) General formula [] (In the formula, R□, R2 and Z each have the same meaning as in the above-mentioned general formula [TV].) General formula [VI] (In the formula, R8 and R4 are each a hydrogen atom , an alkyl group, an unsaturated alkyl group, an aryl group, a heterocyclic group, a vinyl group, or a butadienyl group, and R3 and R1 may be bonded to each other to form a ring.Z represents the general formula [
It has the same meaning as in I[[]. ) General formula [] (wherein, R and R3 each represent the general formula [T'
/] or has the same meaning as in general formula [VI]. ) General formula [■] (In the formula, R4 and Z have the same meanings as in the general formula [rV].) General formula [IX
] Rs [I[I] Also (in the formula, R represents an alkyl group, an unsaturated alkyl group, or an aryl group) General formula [X] [In the formula, R,, R,, R1 and R8 are each Represents a hydrogen atom, a halogen atom, an alkyl group, a vinyl group, a substituted amino group or an aryl group, and R6 also represents -CR
LO (where Ro represents an alkyl group, an aryl group, a heterocyclic group, a vinyl group, an amino group, or an acyloxy group). ] General formula XI (in the formula, Q represents a divalent aromatic hydrocarbon group or a divalent heterocyclic group). may have.
−a式[I1]〜[X]のそれぞれにおいてノ10ゲン
原子としては、フッ素原子、塩素原子、臭素原子、ヨウ
素原子等が挙げられ、置換もしくは無置換のアルキル基
としては例えばメチル基、エチル基、n−プロピル基、
n−ブチル基、イソブチル基、tert−ブチル基、n
−ヘキシル基、n−オクチル基、ベンジル基、p−メチ
ルベンジル基、p−クロルベンジル基、2−フェニルエ
チル基、1−ナフチルメチル基、2−ナフチルメチル基
、アリル基、2−ヒドロキシエチル基、2−メトキシエ
チル基、3−モルホリノプロピル基、2−ジエチルアミ
ノエチル基、3−カルバゾリルメチル基等が挙げられる
。R□で表わされる低級アルキル基は通常これらのうち
炭素原子数が1〜6のアルキル基を示す。-a In each of formulas [I1] to [X], examples of the hydrogen atom include fluorine atom, chlorine atom, bromine atom, iodine atom, etc., and examples of the substituted or unsubstituted alkyl group include methyl group, ethyl group, etc. group, n-propyl group,
n-butyl group, isobutyl group, tert-butyl group, n
-Hexyl group, n-octyl group, benzyl group, p-methylbenzyl group, p-chlorobenzyl group, 2-phenylethyl group, 1-naphthylmethyl group, 2-naphthylmethyl group, allyl group, 2-hydroxyethyl group , 2-methoxyethyl group, 3-morpholinopropyl group, 2-diethylaminoethyl group, 3-carbazolylmethyl group, and the like. The lower alkyl group represented by R□ usually represents an alkyl group having 1 to 6 carbon atoms.
アリール基としては、フェニル基、ナフチル基、アント
リル基、ピレニル基、フェナントリル基、アントラキノ
リル基、アセナフチル基、フルオレニル基、ビフェニリ
ル基、p−ターフェニリル基、p−スチリルフェニル基
、などの芳香族炭化水素基が挙げられ、これらの置換基
としては、メチル基、エチル基、ブチル基等のアルキル
基;フッ素、塩素、臭素、ヨウ素等のハロゲン原子;メ
トキシ基、エトキシ基、ブトキシ基等のアルコキシ基;
フェノキシ基等のアリーロキシ基;ヒドロキシル基;ニ
トロ基;シアノ基;アミノ基;ジメチルアミノ基、ジエ
チルアミノ基、ジベンジルアミノ基等の置換アミノ基;
カルボキシル基;エトキシカルボニル基等のアルコキシ
カルボニル基;フエニロキシカルボニル基等のアリーロ
キシカルボニル基;アセトキシ基、ベンゾイルオキシ基
等のアシロキシ基;アセチル基、ベンゾイル基等のアシ
ル基;カルバモイル基、ジメチルアミノカルボニル基、
フェニルアミノカルボニル基等の置換アミノカルボニル
基;ベンジルオキシ基、フェネチルオキシ基等のアリー
ルアルコキシ基等が挙げられる。Examples of the aryl group include aromatic hydrocarbon groups such as phenyl group, naphthyl group, anthryl group, pyrenyl group, phenanthryl group, anthraquinolyl group, acenaphthyl group, fluorenyl group, biphenylyl group, p-terphenylyl group, and p-styrylphenyl group. These substituents include alkyl groups such as methyl, ethyl, and butyl; halogen atoms such as fluorine, chlorine, bromine, and iodine; alkoxy groups such as methoxy, ethoxy, and butoxy;
Aryloxy groups such as phenoxy groups; hydroxyl groups; nitro groups; cyano groups; amino groups; substituted amino groups such as dimethylamino groups, diethylamino groups, and dibenzylamino groups;
Carboxyl group; alkoxycarbonyl group such as ethoxycarbonyl group; aryloxycarbonyl group such as phenyloxycarbonyl group; acyloxy group such as acetoxy group, benzoyloxy group; acyl group such as acetyl group, benzoyl group; carbamoyl group, dimethylamino carbonyl group,
Substituted aminocarbonyl groups such as a phenylaminocarbonyl group; arylalkoxy groups such as a benzyloxy group and a phenethyloxy group; and the like.
複素環基としては、フリル基、チエニル基、チアゾリル
基、インドリル基、ピロリル基、カルバゾリル基、ピリ
ジル基、モルホリノ基、キノリル基、イミダゾリル基、
オキサシリル基、トリアゾリル基、ピペリジル基、ベン
ゾオキサシリル基、ベンゾイミダゾリル基、ベンゾチア
ゾリル基、アクリジル基、キサンテニル基、フェナジニ
ル基、フェノチアジニル基、クマリニル基、等が挙げら
れ、アリール基と同様の置換基を有していてもよい。Examples of the heterocyclic group include furyl group, thienyl group, thiazolyl group, indolyl group, pyrrolyl group, carbazolyl group, pyridyl group, morpholino group, quinolyl group, imidazolyl group,
Examples include oxasilyl group, triazolyl group, piperidyl group, benzoxacylyl group, benzimidazolyl group, benzothiazolyl group, acridyl group, xanthenyl group, phenazinyl group, phenothiazinyl group, coumarinyl group, etc., which have the same substituents as the aryl group. You may do so.
アルコキシ基としてはメトキシ基、エトキシ基等が挙げ
られ、アリールオキシ基としては、フェノキシ基、p−
クロロフェノキシ基、p−メチルフェノキシ基、1−ナ
フトキシ基等が挙げられ、アラルキルオキシ基としては
、ベンジルオキシ基、フェネチルオキシ基等が挙げられ
る。Examples of the alkoxy group include methoxy group and ethoxy group, and examples of the aryloxy group include phenoxy group and p-
Examples of the aralkyloxy group include a chlorophenoxy group, p-methylphenoxy group, and 1-naphthoxy group, and examples of the aralkyloxy group include a benzyloxy group and a phenethyloxy group.
アルコキシカルボニル基としてはメトキシカルボニル基
、エトキシカルボニル基等が挙げられ、アリールオキシ
カルボニル基としては、フェノキシカルボニル基、1−
ナフトキシカルボニル基等が挙げられる。Examples of the alkoxycarbonyl group include a methoxycarbonyl group and an ethoxycarbonyl group, and examples of the aryloxycarbonyl group include a phenoxycarbonyl group and a 1-
Examples include naphthoxycarbonyl group.
Zとしては、ベンゼン環と縮合してナフタリン環、アン
トラセン環、カルバゾール環、ベンゾカルバゾール環、
ジベンゾフラン環等の芳香族炭化水素または複素環を形
成するに要する2価の基が挙げられる。Z is fused with a benzene ring to form a naphthalene ring, anthracene ring, carbazole ring, benzocarbazole ring,
Examples include divalent groups required to form an aromatic hydrocarbon or a heterocycle such as a dibenzofuran ring.
R1およびR7が互いに結合して形成する環基の例とし
ては、シクロへキシリデン基、インデニリデン基、フル
オレニリデン基、ペンタメチレン基等が挙げられる。Examples of the ring group formed by bonding R1 and R7 to each other include a cyclohexylidene group, an indenylidene group, a fluorenylidene group, and a pentamethylene group.
不飽和アルキル基の例としては、アリル基、3−ブテニ
ル基、シンナミル基等が挙げられる。Examples of unsaturated alkyl groups include allyl group, 3-butenyl group, cinnamyl group, and the like.
一般式[XI]中のQは置換基を有していてもよい2価
の芳香族炭化水素基または置換基を有していてもよい2
価の複素環基を示す。2価の芳香族炭化水素基としては
、例えば0−フミニレン基等の2価の単環式芳香族炭化
水素基、0−ナフチレン基、18−ナフチレン基、1,
2−アントラキノニレン基、9.10−フエナントリレ
ン基等の2価の縮合多環式芳香族炭化水素基等が挙げら
れる。Q in general formula [XI] is a divalent aromatic hydrocarbon group that may have a substituent or 2 that may have a substituent
represents a valent heterocyclic group. Examples of divalent aromatic hydrocarbon groups include divalent monocyclic aromatic hydrocarbon groups such as 0-humylene group, 0-naphthylene group, 18-naphthylene group, 1,
Examples include divalent condensed polycyclic aromatic hydrocarbon groups such as a 2-anthraquinonylene group and a 9.10-phenanthrylene group.
また、2価の複素環基としては、例えば、3゜4−ピラ
ゾールジイル基、2,3−ピリジンジイル基、3,4−
ピリジンジイル基、4,5−ピリミジンジイル基、6.
7−インダゾールジイル基、56−ベンズイミダゾール
ジイル基、5.6−キラリンジイル基等の2価の複素環
基等が挙げられる。Further, as the divalent heterocyclic group, for example, 3゜4-pyrazolediyl group, 2,3-pyridinediyl group, 3,4-
Pyridinediyl group, 4,5-pyrimidinediyl group, 6.
Divalent heterocyclic groups such as 7-indazolediyl group, 56-benzimidazolediyl group, and 5,6-chiralindiyl group can be mentioned.
これらの基の置換基としては、例えばメチル基、エチル
基、n−プロピル基、i−プロピル基、n−ブチル基、
i−ブチル基、n−ヘキシル基等のアルキル基;トリフ
ルオルメチル基;メトキシ基、エトキシ基、プロポキシ
基、ブトキシ基等のアルコキシ基;ヒドロキシル基;ニ
トロ基;シアノ基;アミノ基;ジメチルアミノ基、ジエ
チルアミノ基、ジベンジルアミノ基等の置換アミノ基;
弗素原子、塩素原子、臭素原子、ヨウ素原子等のハロゲ
ン原子;カルボキシル基;エトキシカルボニル基等のア
ルコキシカルボニル基;カルバモイル基;アセチル基、
ベンゾイル基等のアシル基;フェノキシ基等のアリーロ
キシ基;ベンジルオキシ基等のアリールアルコキシ基;
フェニロキシカルボニル基等のアリーロキシカルボニル
基等が挙げられる。中でもアルキル基、アルコキシ基、
ニトロ基、ハロゲン原子、ヒドロキシル基又はカルバモ
イル基、特に、メチル基、メトキシ基、ニトロ基、塩素
原子又はヒドロキシル基が好ましい。Examples of substituents for these groups include methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group,
Alkyl groups such as i-butyl group and n-hexyl group; trifluoromethyl group; alkoxy groups such as methoxy group, ethoxy group, propoxy group, butoxy group; hydroxyl group; nitro group; cyano group; amino group; dimethylamino group , substituted amino groups such as diethylamino group, dibenzylamino group;
Halogen atoms such as fluorine atom, chlorine atom, bromine atom, iodine atom; carboxyl group; alkoxycarbonyl group such as ethoxycarbonyl group; carbamoyl group; acetyl group;
Acyl groups such as benzoyl groups; aryloxy groups such as phenoxy groups; arylalkoxy groups such as benzyloxy groups;
Examples include aryloxycarbonyl groups such as phenyloxycarbonyl groups. Among them, alkyl groups, alkoxy groups,
A nitro group, a halogen atom, a hydroxyl group or a carbamoyl group, particularly a methyl group, a methoxy group, a nitro group, a chlorine atom or a hydroxyl group are preferred.
本発明においては、カプラー残基Cpが一般式[V]、
[VI]又は[XI]で表わされる基から選ばれる
ことが特に好ましい。In the present invention, the coupler residue Cp has the general formula [V],
Particularly preferred is a group represented by [VI] or [XI].
一般式[I]においてR1−R8のそれぞれで表わされ
る置換基としては、メチル基、エチル基、ブチル基等の
アルキル基;フッ素、塩素、臭素、ヨウ素等のハロゲン
原子;メトキシ基、エトキシ基、ブトキシ基等のアルコ
キシ基;フェノキシ基等のアリーロキシ基;ヒドロキシ
ル基;ニトロ基;シアノ基;アミノ基;ジメチルアミノ
基、ジエチルアミノ基、ジベンジルアミノ基等の置換ア
ミノ基;カルボキシル基;エトキシカルボニル基等のア
ルコキシカルボニル基;フエニロキシカルボニル基等の
アリーロキシカルボニル基;アセトキシ基、ベンゾイル
オキシ基等のアシロキシ基;アセチル基、ベンゾイル基
等のアシル基;カルバモイル基、ジメチルアミノカルボ
ニル基、フェニルアミノカルボニル基等の置換アミノカ
ルボニル基;ベンジルオキシ基、フェネチルオキシ基等
のアリールアルコキシ基、アリール基、複素環基、ヘテ
ロ環基等が挙げられる。Substituents represented by R1 to R8 in general formula [I] include alkyl groups such as methyl, ethyl, and butyl; halogen atoms such as fluorine, chlorine, bromine, and iodine; methoxy, ethoxy, Alkoxy groups such as butoxy groups; aryloxy groups such as phenoxy groups; hydroxyl groups; nitro groups; cyano groups; amino groups; substituted amino groups such as dimethylamino, diethylamino, and dibenzylamino groups; carboxyl groups; ethoxycarbonyl groups, etc. Alkoxycarbonyl group; Aryloxycarbonyl group such as phenyloxycarbonyl group; Acyloxy group such as acetoxy group, benzoyloxy group; Acyl group such as acetyl group, benzoyl group; Carbamoyl group, dimethylaminocarbonyl group, phenylaminocarbonyl group substituted aminocarbonyl groups such as; arylalkoxy groups such as benzyloxy groups and phenethyloxy groups; aryl groups; heterocyclic groups; and heterocyclic groups.
以下に一般式[i]においてCpで表わされるカプラー
残基の具体例を示すが、本発明はこれらによって限定さ
れるものではない。Specific examples of the coupler residue represented by Cp in general formula [i] are shown below, but the present invention is not limited thereto.
以下に一般式[I]において、カプラー残基Cpと結合
するアゾ基を有する基の具体例を示すが、本発明はこれ
らによって限定されるものではない。Specific examples of the group having an azo group bonded to the coupler residue Cp in general formula [I] are shown below, but the present invention is not limited thereto.
[ユー−−を
以下−り1
■−18
本発明の前記一般式[I]で表されるビスアゾ化合物は
、公知の方法により合成することができる。The bisazo compound represented by the general formula [I] of the present invention can be synthesized by a known method.
合成例1
化合物[I]0.01モルを塩酸101gと水201g
中に分散し、5℃以下に保ちつつ亜硝酸ナトリウム00
2モルを水5nJ2に溶解した溶液を滴下した。同温度
で更に1時間攪拌した後、不溶物を濾過除去し、濾液に
六フッ化燐酸アンモニウム4.6gを水501J2に溶
解した溶液を加えた。析出したテトラゾニウム塩を濾取
し、N、N−ジメチルホルムアミド(DMF) 100
1[に溶解した。5℃に保ちながら、化合物(n)0.
02モルをD M F 200.Qに溶解した溶液を滴
下した。ひきつづき5℃以下に保ちながらトリエタノー
ルアミン004モルをD M F 30iflに溶解し
たものを滴下し、5℃以下で1時間、室温で4時間攪拌
した。反応後析出晶を濾取し、DMF洗浄、水洗して乾
燥し、本発明に係る化合物(m) 0.0056モルを
得た。この化合物(m)は元素分析値より本発明に係る
化合物であることが確認された。収率は56%、元素分
析値は下記の通りであった。Synthesis Example 1 0.01 mol of compound [I] was added to 101 g of hydrochloric acid and 201 g of water.
Sodium nitrite 00
A solution of 2 mol dissolved in 5 nJ2 of water was added dropwise. After stirring for another hour at the same temperature, insoluble matter was removed by filtration, and a solution of 4.6 g of ammonium hexafluorophosphate dissolved in 501J2 of water was added to the filtrate. The precipitated tetrazonium salt was collected by filtration and treated with N,N-dimethylformamide (DMF) 100
1 [dissolved in. While maintaining the temperature at 5°C, compound (n) 0.
02 mole to DMF 200. A solution dissolved in Q was added dropwise. Subsequently, while keeping the temperature below 5°C, a solution of 004 mol of triethanolamine in 30 ifl of DMF was added dropwise, followed by stirring at below 5°C for 1 hour and at room temperature for 4 hours. After the reaction, the precipitated crystals were collected by filtration, washed with DMF, washed with water, and dried to obtain 0.0056 mol of the compound (m) according to the present invention. This compound (m) was confirmed to be a compound according to the present invention based on elemental analysis values. The yield was 56%, and the elemental analysis values were as follows.
CHN
計算値(%) 71,23 3.72 9.86実測
値(%) 71,04 3.95 9.78叫白
合成例2
化合物(I’)0.02モル、ならびに水酸化ナトリウ
ム粉末0.05モルをジメチルスルホキシド2にと共に
20℃条件下で攪拌しつつこれに001モルのテトラゾ
ニウムホウフッ化水素酸塩(■′)をジメチルスルホキ
シド32に溶解した溶液を滴下し、そのまま3時間保持
する。反応後反応液に酢酸0.04モルを添加し析出し
たビスアゾ化合物を濾取し、次いでこれを希酢酸、水、
メタノール、テトラヒドロフランにより洗浄後乾燥し、
本発明に係る化合物(■′)を得た。この化合物(■′
)は元素分析値より本発明に係る化合物であることが確
認された。収率は60%、元素分析値は下記の通りであ
った。CHN Calculated value (%) 71,23 3.72 9.86 Actual value (%) 71,04 3.95 9.78 White synthesis example 2 Compound (I') 0.02 mol and sodium hydroxide powder 0 A solution of 001 mole of tetrazonium borohydrofluoride (■') dissolved in dimethyl sulfoxide 32 was added dropwise to this mixture under stirring at 20°C with 0.05 mole of dimethyl sulfoxide 2, and the mixture was kept for 3 hours. do. After the reaction, 0.04 mol of acetic acid was added to the reaction solution, the precipitated bisazo compound was collected by filtration, and then diluted with dilute acetic acid, water,
Washed with methanol and tetrahydrofuran and dried.
A compound (■') according to the present invention was obtained. This compound (■′
) was confirmed to be a compound according to the present invention based on elemental analysis values. The yield was 60%, and the elemental analysis values were as follows.
CHN
計算値(%) 73,74 3.24 14.08実
測値(%) 73,59 3.45 14.04合成
例3
化合物(1’)0.01モルとナフトールA3001モ
ルをジメチルスルホキシド3りに溶解する。CHN Calculated value (%) 73,74 3.24 14.08 Actual value (%) 73,59 3.45 14.04 Synthesis example 3 0.01 mole of compound (1') and 1 mole of naphthol A were mixed with 3 dimethyl sulfoxide. dissolve in
この溶液を20〜23℃の温度に保ちながら化合物(I
I’ ) 0.01モルをジアゾ化して得られたテトラ
ゾニウムホウフッ化水素酸塩(■′)をジメチルスルホ
キシド22に溶解した溶液を加えた後、攪拌しつつ、酢
酸ナトリウム0.02モルを水201Qに溶解した溶液
を滴下し、そのまま3時間攪拌する。Compound (I) was added while keeping this solution at a temperature of 20-23°C.
I') After adding a solution of tetrazonium borohydrofluoride (■') obtained by diazotizing 0.01 mol in dimethyl sulfoxide 22, 0.02 mol of sodium acetate was added while stirring. A solution dissolved in water 201Q was added dropwise, and the mixture was stirred for 3 hours.
析出した沈殿を濾別し、ジメチルスルホキシド、希酢酸
、水、メタノール、テトラヒドロフランで洗浄後乾燥し
、その後単離し、本発明に係る化合物(■′)を得た。The deposited precipitate was separated by filtration, washed with dimethyl sulfoxide, dilute acetic acid, water, methanol, and tetrahydrofuran, dried, and then isolated to obtain a compound (■') according to the present invention.
この化合物(■′)は元素分析値、吸収スペクトルより
本発明に係る化合物であることが確認された。収率は4
0%、元素分析値は下記の通りであった。This compound (■') was confirmed to be a compound according to the present invention based on elemental analysis and absorption spectrum. The yield is 4
0%, and the elemental analysis values were as follows.
HN
計算値(%) 77.34 3.91 10.94実
測値(%) 77.29 4.06 10.83本発
明の他の化合物も、前記合成例と同様にして作ることが
出来る。HN Calculated value (%) 77.34 3.91 10.94 Actual value (%) 77.29 4.06 10.83 Other compounds of the present invention can also be produced in the same manner as in the above synthesis example.
本発明に係る前記ビスアゾ化合物は優れた光導電性を有
し、これをバインダー中に分散した感光層を導電性支持
体上に設けることにより本発明の電子写真感光体を製造
することができる。本発明に係るビスアゾ化合物は、そ
の優れたキャリア発生能を利用して、これをキャリア発
生物質として用い、これと組み合わせて有効に作用し得
るキャリア輸送物質を共に用いることにより、いわゆる
機能分離型の感光体とすることができる。前記機能分離
型感光体は前記両物質の混合分散型のものであってもよ
いが、本発明に係るビスアゾ化合物からなるキャリア発
生物質を含むキャリア発生層と、キャリア輸送層とを積
層した積層型感光体とすることがより好ましい。The bisazo compound according to the present invention has excellent photoconductivity, and the electrophotographic photoreceptor of the present invention can be produced by providing a photosensitive layer in which the bisazo compound is dispersed in a binder on a conductive support. The bisazo compound according to the present invention utilizes its excellent carrier generation ability and is used as a carrier generation substance, and by using a carrier transport substance that can effectively act in combination with this, the bisazo compound can be used as a so-called functionally separated type. It can be a photoreceptor. The functionally separated type photoreceptor may be a mixed and dispersed type of both of the above substances, but it may be a laminate type in which a carrier generation layer containing a carrier generation substance made of a bisazo compound according to the present invention and a carrier transport layer are laminated. It is more preferable to use a photoreceptor.
尚、積層構成の感光層の場合キャリア発生層は入射光量
の大部分が電荷発生層で吸収されて多くの電荷発生キャ
リアを生成すると共に発生した電荷キャリアを再結合や
捕獲(トラップ)により失活することなくキャリア輸送
層に注入するために光キャリアを生成するのに十分な膜
厚の範囲でできる限り薄膜層とすることが好ましい。In the case of a photosensitive layer with a laminated structure, most of the incident light is absorbed by the charge generation layer, generating many charge generation carriers, and the generated charge carriers are deactivated by recombination or trapping. It is preferable to make the layer as thin as possible within a range of thickness sufficient to generate photocarriers in order to inject them into the carrier transport layer without causing damage.
またキャリア輸送層は前述のキャリア発生層と電気的に
接合されており、電界の存在下で電荷発生層から注入さ
れた電荷キャリアを表面まで輸送できる機能を有してい
る。Further, the carrier transport layer is electrically connected to the carrier generation layer described above, and has a function of transporting charge carriers injected from the charge generation layer to the surface in the presence of an electric field.
また単層構成の機能分離型感光体においては、単層で光
キャリアの発生及び輸送を行うもので層内でキャリア発
生物質とキャリア輸送物質が電気的に接合されているか
、かつ/またはキャリア発生物質もキャリアの輸送に寄
与するものである。In addition, in a functionally separated photoreceptor with a single layer structure, photocarriers are generated and transported in a single layer, and the carrier generation substance and the carrier transport substance are electrically bonded within the layer, and/or the carrier generation substance and the carrier transport substance are electrically bonded within the layer. Substances also contribute to carrier transport.
また、キャリア発生層にキャリア発生物質とキャリア輸
送物質の一部の両方が含有されていてもよい。いずれの
層構成においても、感光層の上に保護層を設けても良く
、また支持体と感光層の間にバリア機能と接着性を持っ
下引層(中間層)を設けても良い。Further, the carrier generation layer may contain both the carrier generation substance and a part of the carrier transport substance. In either layer structure, a protective layer may be provided on the photosensitive layer, and a subbing layer (intermediate layer) having a barrier function and adhesive property may be provided between the support and the photosensitive layer.
感光層、保護層、下引層に使用可能なバインダー樹脂と
しては、例えばポリスチレン、ポリエチレン、ポリプロ
ピレン、アクリル樹脂、メタクリル樹脂、塩化ビニル樹
脂、酢酸ビニル樹脂、ポリビニルブチラール樹脂、エポ
キシ樹脂、ポリウレタン樹脂、フェノール樹脂、ポリエ
ステル樹脂、アルキッド樹脂、ポリカーボネート樹脂、
シリコン樹脂、メラミン樹脂、等の付加重合型樹脂、重
付加型樹脂、重縮合型樹脂、並びにこれらの樹脂の繰り
返し単位のうちの2つ以上を含む共重合体樹脂等が挙げ
られる。またこれらの絶縁性樹脂の他、ポリ−N−ビニ
ルカルバゾール等の高分子有機半導体が挙げられる。Examples of binder resins that can be used for the photosensitive layer, protective layer, and subbing layer include polystyrene, polyethylene, polypropylene, acrylic resin, methacrylic resin, vinyl chloride resin, vinyl acetate resin, polyvinyl butyral resin, epoxy resin, polyurethane resin, and phenol. resin, polyester resin, alkyd resin, polycarbonate resin,
Examples include addition polymer resins such as silicone resins and melamine resins, polyaddition resins, polycondensation resins, and copolymer resins containing two or more repeating units of these resins. In addition to these insulating resins, polymeric organic semiconductors such as poly-N-vinylcarbazole may also be used.
又、感光層中にはキャリア発生物質のキャリア発生機能
を改善する目的で有機アミン類を添加することができ、
特に2級アミンを添加するのが好ましい。かかる有機ア
ミンの添加量としては、キャリア発生物質に対して該キ
ャリア発生物質の1倍以下、好ましくは0.2倍〜00
05倍の範囲のモル数とするのがよい。Furthermore, organic amines can be added to the photosensitive layer for the purpose of improving the carrier generation function of the carrier generation substance.
In particular, it is preferable to add a secondary amine. The amount of the organic amine added is 1 times or less, preferably 0.2 to 0.0 times the amount of the carrier generating substance, relative to the carrier generating substance.
The number of moles is preferably in the range of 0.05 times.
又、上記感光層においては、オゾン劣化防止の目的でヒ
ンダードフェノール類、ヒンダードアミン類、パラフェ
ニレンジアミン類、ハイドロキノン類、有機燐化合物類
等の酸化防止剤を添加することができる。Further, in the photosensitive layer, antioxidants such as hindered phenols, hindered amines, para-phenylene diamines, hydroquinones, and organic phosphorus compounds may be added for the purpose of preventing ozone deterioration.
これらの化合物はゴム、プラスチック、油脂類等の酸化
防止剤として知られており、市販品を容易に入手できる
。These compounds are known as antioxidants for rubber, plastics, oils and fats, and are easily available commercially.
これらの酸化防止剤はキャリア発生層、キャリア輸送層
、又は保護層のいずれに添加されてもよいが、好ましく
はキャリア輸送層に添加される。These antioxidants may be added to any of the carrier generation layer, carrier transport layer, or protective layer, but are preferably added to the carrier transport layer.
その場合の酸化防止剤の添加量はキャリア輸送物質10
0重量部に対して0.1〜100重量部、好ましくは1
〜50重量部、特に好ましくは5〜25重量部である。In that case, the amount of antioxidant added is 10 parts of the carrier transport substance.
0.1 to 100 parts by weight, preferably 1 part by weight
~50 parts by weight, particularly preferably 5 to 25 parts by weight.
次に前記感光層を支持する導電性支持体としては、アル
ミニュウム、ニッケルなどの金属板、金属ドラム又は金
属箔をラミネートした、或はアルミニュウム、酸化錫、
酸化インジュウムなどを蒸着したプラスチックフィルム
あるいは導電性物質を塗布した紙、プラスチックなどの
フィルム又はドラムを使用することができる。Next, the conductive support supporting the photosensitive layer may be a metal plate made of aluminum, nickel, etc., a metal drum, or a metal foil laminated, or made of aluminum, tin oxide, etc.
A plastic film coated with indium oxide or the like, or a paper or plastic film coated with a conductive substance, or a drum can be used.
本発明において、キャリア発生層は代表的には前述の本
発明に係るビスアゾ化合物を適当な分散媒に単独もしく
は適当なバインダ樹脂と共に分散せしめた分散液を例え
ばデイツプ塗布、スプレィ塗布、ブレード塗布、ロール
塗布等によって支持体若しくは下引層上又はキャリア輸
送層上に塗布して乾燥させる方法により設けることがで
きる。In the present invention, the carrier generation layer is typically formed by applying a dispersion of the bisazo compound according to the present invention described above in a suitable dispersion medium alone or together with a suitable binder resin, for example, by dip coating, spray coating, blade coating, or roll coating. It can be provided by a method of coating the support, subbing layer, or carrier transport layer by coating and drying.
また本発明に係るビスアゾ化合物の分散にはボールミル
、ホモミキサ、サンドミル、超音波分散機、アトライタ
等が用いられる。Further, for dispersing the bisazo compound according to the present invention, a ball mill, a homomixer, a sand mill, an ultrasonic disperser, an attritor, etc. are used.
本発明に係るビスアゾ化合物の分散媒としては、例えば
ヘキサン、ベンゼン、トルエン、キシレン等の炭化水素
類;メチレンクロライド、1.2−ジクロルエタン、5
yI11−テトラクロルエタン、11.2−トリクロル
エタン、クロロホルム等のハロゲン化炭化水素;アセト
ン、メチルエチルケトン、シクロヘキサノン等のケトン
類;酢酸エチル、酢酸ブチル等のエステル類;メタノー
ル、エタノール、プロパツール、ブタノール、シクロヘ
キサノール、ヘプタツール、エチレングリコール、メチ
ルセルソルブ、エチルセルソルブ、酢酸セルソルブ等の
アルコール類及びこの誘導体;テトラヒドロフラン、1
.4−ジオキサン、フラン、フルフラール等のエーテル
、アセタール類;ピリジンやブチルアミン、ジエチルア
ミン、エチレンジアミン、イソプロパツールアミン等の
アミン類;NN−ジメチルホルムアミド等のアミド類等
の窒素化合物、その他脂肪酸及びフェノール類、二硫化
炭素や燐酸トリエチル等の硫黄、燐化合物等の1種又は
2種以上を用いることができる。Examples of the dispersion medium for the bisazo compound according to the present invention include hydrocarbons such as hexane, benzene, toluene, and xylene; methylene chloride, 1,2-dichloroethane, and
yI Halogenated hydrocarbons such as 11-tetrachloroethane, 11.2-trichloroethane and chloroform; Ketones such as acetone, methyl ethyl ketone and cyclohexanone; Esters such as ethyl acetate and butyl acetate; methanol, ethanol, propatool, butanol, Alcohols such as cyclohexanol, heptatool, ethylene glycol, methyl cellosolve, ethyl cellosolve, acetic acid cellosolve and derivatives thereof; tetrahydrofuran, 1
.. Ethers and acetals such as 4-dioxane, furan, and furfural; Amines such as pyridine, butylamine, diethylamine, ethylenediamine, and isopropanolamine; Nitrogen compounds such as amides such as NN-dimethylformamide; other fatty acids and phenols; One or more types of sulfur and phosphorus compounds such as carbon disulfide and triethyl phosphate can be used.
本発明の感光体が積層型構成の場合、キャリア発生層中
のバインダ:キャリア発生物質:キャリア輸送物質の重
量比は0〜100:1〜500:O〜500が好ましい
。When the photoreceptor of the present invention has a laminated structure, the weight ratio of binder:carrier generating substance:carrier transporting substance in the carrier generating layer is preferably 0 to 100:1 to 500:O to 500.
キャリア発生物質の含有割合がこれより少ないと感度が
低く、残留電位の増加を招き、またこれより多いと暗減
衰及び受容電位が低下する。If the content of the carrier-generating substance is less than this, the sensitivity will be low and the residual potential will increase, and if it is more than this, the dark decay and acceptance potential will decrease.
以上のようにして形成されるキャリア発生層の膜厚は、
好ましくは0.01〜10μm1特に好ましくは01〜
5μmである。The thickness of the carrier generation layer formed as described above is
Preferably 0.01 to 10 μm1, particularly preferably 0.1 to 10 μm1
It is 5 μm.
本発明においてキャリア輸送層は、キャリア輸送物質を
適当な分散媒に単独であるいは上述のノくインダ樹脂と
共に溶解分散せしめたものを塗布、乾燥して形成するこ
とができる。用いられる分散媒としては前記キャリア発
生物質の分散において用いた分散媒を用いることができ
る。In the present invention, the carrier transport layer can be formed by applying and drying a carrier transport substance dissolved and dispersed in a suitable dispersion medium alone or together with the above-mentioned binder resin. As the dispersion medium used, the dispersion medium used in dispersing the carrier-generating substance can be used.
本発明において使用可能なキャリア輸送物質としては、
特に制限はないが、例えばオキサゾール誘導体、オキサ
ジアゾール誘導体、チアゾール誘導体、チアジアゾール
誘導体、トリアゾール誘導体、イミダゾール誘導体、イ
ミダシロン誘導体、イミダゾリジン誘導体、ビスイミダ
ゾリジン誘導体、スチリル化合物、ヒドラゾン化合物、
ピラゾリン化合物、アミン誘導体、オキサシロン誘導体
、ベンゾチアゾール誘導体、ベンズイミダゾール誘導体
、キナゾリン誘導体、ベンゾフラン誘導体、アクリジン
誘導体、フェナジン誘導体、アミノスチルベン誘導体、
ポリ−N−ビニルカルバゾール、ポリ−1−ビニルピレ
ン、ポリ−9−ビニルアントラセン等である。Carrier transport substances that can be used in the present invention include:
Although not particularly limited, examples include oxazole derivatives, oxadiazole derivatives, thiazole derivatives, thiadiazole derivatives, triazole derivatives, imidazole derivatives, imidasilone derivatives, imidazolidine derivatives, bisimidazolidine derivatives, styryl compounds, hydrazone compounds,
Pyrazoline compounds, amine derivatives, oxacilone derivatives, benzothiazole derivatives, benzimidazole derivatives, quinazoline derivatives, benzofuran derivatives, acridine derivatives, phenazine derivatives, aminostilbene derivatives,
These include poly-N-vinylcarbazole, poly-1-vinylpyrene, poly-9-vinylanthracene, and the like.
本発明において用いられるキャリア輸送物質としては光
照射時発生するホールの支持体側への輸送能力が優れて
いる他、前記本発明に係るビスアゾ化合物との組合せに
好適なものが好ましくもちいられ、かかるキャリア輸送
物質として好ましいものは、下記一般式(A)、(B)
及び(C)で表されるものが挙げられる。The carrier transport substance used in the present invention is preferably one that has an excellent ability to transport holes generated during light irradiation to the support side and is suitable for combination with the bisazo compound according to the present invention. Preferred transport substances are the following general formulas (A) and (B):
and (C).
一般式(A)
式中、Ar□、Ar2及びAr、はそれぞれ置換もしく
は非置換のアリール基を表し、Araは置換もしくは非
置換のアリーレン基を表し、Rは水素原子、置換もしく
は非置換のアルキル基又は置換もしくは非置換のアリー
ル基を表す。General formula (A) In the formula, Ar□, Ar2 and Ar each represent a substituted or unsubstituted aryl group, Ara represents a substituted or unsubstituted arylene group, and R is a hydrogen atom, a substituted or unsubstituted alkyl represents a group or a substituted or unsubstituted aryl group.
このような化合物の具体例は特開昭58−65440号
公報明細書の第3〜4頁及び同58−198043号公
報明細書の第3〜6頁に詳細に記載されている。Specific examples of such compounds are described in detail on pages 3 to 4 of the specification of JP-A-58-65440 and pages 3-6 of the specification of JP-A-58-198043.
一般式
式中R□は置換もしくは非置換のアリール基又は置換も
しくは非置換の複素環基であり、R2は水素原子、置換
もしくは非置換のアルキル基、又は置換もしくは非置換
のアリール基を表し、詳細には特開昭58−13464
2号及び同58−166354記載公報明細書に記゛載
されている。In the general formula, R□ is a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group, R2 represents a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, For details, see Japanese Patent Application Publication No. 58-13464.
No. 2 and No. 58-166354.
一般式(C)
式中R□は置換もしくは非置換のアリール基であり、R
2は水素原子、ハロゲン原子、ヒドロキシ基、置換もし
くは非置換のアルキル基、置換もしくは非置換のアルコ
キシ基又は置換もしくは非置換のアミノ基であり、Rs
は置換もしくは非置換のアリール基又は置換もしくは非
置換の複素環基を表わす。これらの化合物の合成法及び
その例示化合物については特公昭57−148750号
公報明細書に詳細に記載されており、本発明に援用する
ことができる。General formula (C) In the formula, R□ is a substituted or unsubstituted aryl group, and R
2 is a hydrogen atom, a halogen atom, a hydroxy group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, or a substituted or unsubstituted amino group, and Rs
represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group. Synthesis methods for these compounds and exemplified compounds thereof are described in detail in Japanese Patent Publication No. 148750/1982, which can be incorporated into the present invention.
本発明に用いられるその他の好ましいキャリア輸送物質
としては、特公昭57−67940号、同59−152
52号及び同57−101844号公報明細書にそれぞ
れ記載されているヒドラゾン化合物を挙げることができ
る。Other preferable carrier transport materials used in the present invention include Japanese Patent Publications Nos. 57-67940 and 59-152.
Examples include hydrazone compounds described in Japanese Patent No. 52 and No. 57-101844, respectively.
本発明においてキャリア輸送物質の添加量は、キャリア
輸送層中のバインダ樹脂100重量部に対してキャリア
輸送物質20〜200重量部が好ましく、特に好ましく
は30〜150重量部である。In the present invention, the amount of the carrier transport substance added is preferably 20 to 200 parts by weight, particularly preferably 30 to 150 parts by weight, based on 100 parts by weight of the binder resin in the carrier transport layer.
形成されるキャリア輸送層の膜厚は、好ましくは5〜5
0μm1特に好ましくは5〜30μmである。The thickness of the carrier transport layer to be formed is preferably 5 to 5.
0 μm1, particularly preferably 5 to 30 μm.
また、本発明に係るビスアゾ化合物を用いる単層機能分
離型の電子写真感光体の場合は、バインダ:ビスアゾ化
合物:キャリア輸送物質の割合は0〜100:1〜50
0:O〜500が好ましく、形成される感光層の膜厚は
5〜50μmが好ましく、特に好ましくは5〜30μm
である。Further, in the case of a monolayer functionally separated electrophotographic photoreceptor using the bisazo compound according to the present invention, the ratio of binder: bisazo compound: carrier transport substance is 0 to 100:1 to 50.
0:0 to 500 is preferable, and the thickness of the photosensitive layer to be formed is preferably 5 to 50 μm, particularly preferably 5 to 30 μm.
It is.
本発明においてキャリア発生層には感度の向上、残留電
位乃至反復使用時の疲労低減等を目的として、一種又は
二種以上の電子受容性物質を含有せしめることができる
。電子受容性物質の添加割合は重量比で、本発明に係る
ビスアゾ化合物二電子受容性物質= 100 : 0.
01〜200が好ましく、更に好ましくは100 :
0.1〜100である。In the present invention, the carrier generation layer may contain one or more electron-accepting substances for the purpose of improving sensitivity, reducing residual potential or fatigue during repeated use, etc. The addition ratio of the electron-accepting substance is a weight ratio of bisazo compound two-electron-accepting substance according to the present invention = 100:0.
01 to 200 is preferable, more preferably 100:
It is 0.1-100.
電子受容性物質はキャリア輸送層に添加してもよく、こ
の場合の電子受容性物質の添加割合は重量比で、全キャ
リア輸送物質:電子受容性物質−100: 0.01〜
100が好ましく、更に好ましくは100:0.1〜5
0である。The electron-accepting substance may be added to the carrier transport layer, and in this case, the ratio of the electron-accepting substance added is, by weight, the total carrier-transporting substance:electron-accepting substance-100:0.01~
100 is preferable, more preferably 100:0.1-5
It is 0.
また本発明の感光体には、その他、必要により感光層を
保護する目的で紫外線吸収剤、酸化防止剤等を含有して
もよく、また感色性補正の染料を含有してもよい。In addition, the photoreceptor of the present invention may also contain, if necessary, an ultraviolet absorber, an antioxidant, etc. for the purpose of protecting the photosensitive layer, and may also contain a dye for color sensitivity correction.
[発明の効果コ
以上詳しく説明したように、本発明により、広範なキャ
リア輸送物質との組合せが可能でしかもキャリア発生能
に優れた特定のビスアゾ化合物を含有することにより、
かつ高感度で感色性も良好であり、特に繰り返し使用し
た時にも感度、帯電性、残留電位の変動が少なく、耐久
性がきわめて優れた電子写真感光体を提供することがで
きる。[Effects of the Invention] As explained in detail above, according to the present invention, by containing a specific bisazo compound that can be combined with a wide range of carrier transport substances and has excellent carrier generation ability,
Moreover, it is possible to provide an electrophotographic photoreceptor that has high sensitivity and good color sensitivity, has little variation in sensitivity, chargeability, and residual potential even after repeated use, and has extremely excellent durability.
また本発明の感光体は電子写真方式の普通紙複写機のみ
でなく、レーザープリンター、LEDプリンター等のプ
リンター用感光体としても適している。更に本発明に係
るビスアゾ化合物は電界発光素子にも有効に用いること
ができる。Further, the photoreceptor of the present invention is suitable not only for electrophotographic plain paper copying machines but also as a photoreceptor for printers such as laser printers and LED printers. Furthermore, the bisazo compound according to the present invention can also be effectively used in electroluminescent devices.
[実施例]
以下、本発明を実施例によって具体的に説明するが、本
発明はこれらによって限定されるものではない。[Examples] Hereinafter, the present invention will be specifically explained with reference to Examples, but the present invention is not limited thereto.
実施例1
ポリエステルフィルム上にアルミニウム箔をラミネート
して成る導電性支持体上に、塩化ビニル−酢酸ビニル−
無水マレイン酸共重合体[エスレックMF−104(積
木化学社製)よりなる厚さ0.05μmの中間層を設け
、その上にキャリア発生物質(CGM)として下記ビス
アゾ化合物(A−2)を2gとポリビニルブチラール樹
脂「エスレックBH−3J (漬水化学工業社製)
2gとをテトラヒドロフラン110−に加え、ボールミ
ルで12時間分散した。この分散液を乾燥時の膜厚が、
0.5μmになるように塗布し、キャリア発生層とし、
さらにその上に、キャリア輸送層として、下記構造式の
キャリア輸送物質(K−1)6gとポリカーボネート樹
脂「ニーピロンZ−200J (三菱ガス化学社製)
10gを1,2−ジクロルエタン80vfiに溶解した
液を乾燥後の膜厚が18μmになるように塗布して、キ
ャリア輸送層を形成し、本発明の感光体試料No、1を
作成した。次いでキャリア発生物質及びキャリア輸送物
質を第1表に示すようにかえた以外は同様にして感光体
試料No、2〜19を作成した。Example 1 Vinyl chloride-vinyl acetate-
A 0.05 μm thick intermediate layer made of maleic anhydride copolymer [S-LEC MF-104 (manufactured by Block Chemical Co., Ltd.) was provided, and 2 g of the following bisazo compound (A-2) was added as a carrier generating substance (CGM) on top of it. and polyvinyl butyral resin “S-LEC BH-3J (manufactured by Tsukumi Kagaku Kogyo Co., Ltd.)”
2 g was added to 110-g of tetrahydrofuran and dispersed in a ball mill for 12 hours. The film thickness when this dispersion is dried is
Coating to a thickness of 0.5 μm to form a carrier generation layer,
Furthermore, as a carrier transport layer, 6 g of a carrier transport substance (K-1) with the following structural formula and a polycarbonate resin "Nipilon Z-200J (manufactured by Mitsubishi Gas Chemical Co., Ltd.)"
A carrier transport layer was formed by dissolving 10 g of the carrier transport layer in 80 vfi of 1,2-dichloroethane and applying the solution to a dry film thickness of 18 μm, thereby producing photoreceptor sample No. 1 of the present invention. Next, photoreceptor samples Nos. 2 to 19 were prepared in the same manner except that the carrier-generating substance and the carrier-transporting substance were changed as shown in Table 1.
以上のようにして得られた感光体を四用口電機製作所E
P A−8100型静電複写紙試験機を用いて、以下
の特性評価を行なった。すなわち帯電圧−6KVで5秒
間帯電した後、5秒間放置し、次いで感光体表面での照
度35ルクス・秒になるようにハロゲンランプ光を照射
して、表面電位(Vo)及び表面電位を半分に減衰させ
るのに用する露光量(半減露光量)El/2を求めた。The photoreceptor obtained in the above manner was
The following characteristics were evaluated using a PA-8100 electrostatic copying paper tester. That is, after charging with a charging voltage of -6 KV for 5 seconds, leaving it for 5 seconds, and then irradiating it with halogen lamp light so that the illumination intensity on the photoreceptor surface is 35 lux · seconds, the surface potential (Vo) and the surface potential are halved. The exposure amount (half-reduced exposure amount) El/2 used for attenuation was determined.
結果を第1表に示す。The results are shown in Table 1.
以下・余白
く
く
く
く
く
工
く
=
工
に−1
に−2
に−3
に−4
に−5
に−8
に−10
以下丞p
比較例1
キャリア発生物質として下記ビスアゾ化合物(G−1)
を用いた他は、実施例1と同様にして比較用感光体試料
No、20を作成した。Below, fill in the blanks = -1 to -2 to -3 to -4 to -5 to -8 to -10 below: Comparative Example 1 The following bisazo compound (G-1) was used as a carrier-generating substance.
Comparative photoreceptor sample No. 20 was prepared in the same manner as in Example 1, except that the sample No. 20 was used.
(G−1)
この比較感光体について、実施例1と同様にして測定を
行なったところ、第1表に示す結果を得た。(G-1) Regarding this comparative photoreceptor, measurements were performed in the same manner as in Example 1, and the results shown in Table 1 were obtained.
以″′FTτ余白
ミニjフ
第1表
以上の結果から明らかなように、本発明の感光体は、比
較用感光体に比べ、感度に於て極めて優れたものである
。As is clear from the results shown in Table 1 below, the photoreceptor of the present invention is extremely superior in sensitivity than the comparative photoreceptor.
実施例2
直径60mmのアルミニウム製ドラムの表面に塩化ビニ
ル−酢酸ビニル−無水マレイン酸共重合体[エスレック
MF−104(積水化学社製)より成る厚さ0.05μ
mの中間層を設け、その上にCGMA−1の2gとポリ
ビニルブチラール樹脂「エスレックBH−3J (漬
水化学工業社製) 2gとをテトラヒドロフラン100
dに混合し、ボールミル分散機で24時間分散した分散
液を乾燥後の膜厚が0.6μmになるように塗布し、キ
ャリア発生層を形成した。Example 2 A 0.05μ thick layer made of vinyl chloride-vinyl acetate-maleic anhydride copolymer [S-LEC MF-104 (manufactured by Sekisui Chemical Co., Ltd.)] was coated on the surface of an aluminum drum with a diameter of 60 mm.
2 g of CGMA-1 and 2 g of polyvinyl butyral resin "S-LEC BH-3J (manufactured by Tsukimizu Kagaku Kogyo Co., Ltd.) were placed on top of the intermediate layer of 100 m in tetrahydrofuran.
d and dispersed for 24 hours using a ball mill dispersion machine was applied to form a carrier generation layer so that the film thickness after drying was 0.6 μm.
更にこの上に、前記キャリア輸送物質(K−1)30g
とポリカーボネート樹脂「ニーピロンZ−200J(三
菱瓦斯化学社製)50gとを1,2−ジクロルエタン4
00.(に溶解し、乾燥後の膜厚が18μmになるよう
に塗布してキャリア輸送層を形成し、感光体試料21を
作った。Furthermore, on top of this, 30 g of the carrier transport substance (K-1)
and polycarbonate resin "Nipiron Z-200J (manufactured by Mitsubishi Gas Chemical Co., Ltd.) 50g and 1,2-dichloroethane 4
00. (To form a carrier transport layer, a photoreceptor sample 21 was prepared.
このようにして作成した感光体試料21を電子写真複写
機r U −B ix 1550M RJ (Koni
ca社製)の改造機に装着し、画像を複写したところコ
ントラストが高く、原画に忠実でかつ鮮明な複写画像を
得た。また、本機を高温高湿下(33℃;80%)の環
境試験室内に持って行き、繰り返しの耐久性を試験した
ところ、50 、000回の繰り返しでもコントラスト
が高く鮮明な複写画像が得られた。The photoreceptor sample 21 prepared in this manner was transferred to an electrophotographic copying machine rU-Bix 1550M RJ (Koni
When the image was copied using a modified machine manufactured by CA Corporation, a copy image with high contrast, faithful to the original image, and clear was obtained. In addition, when we took this machine into an environmental test room under high temperature and high humidity conditions (33°C; 80%) to test its durability over repeated use, we were able to obtain clear copied images with high contrast even after 50,000 repetitions. It was done.
比較例2
実施例1の試料No、11におけるキャリア発生物質を
下記構造式(G−2)で表わされるビスアゾ化合物に代
えた他は、実施例2と同様にしてドラム状の比較用感光
体試料N o、22を作成し、実施例2と同様にして複
写画像を評価したところ、高温高湿下の繰り返し耐久性
において、30,000回あたりからはコントラストが
低下し、カブリの多い画像しか得られなかった。Comparative Example 2 A drum-shaped comparative photoreceptor sample was prepared in the same manner as in Example 2, except that the carrier-generating substance in Sample No. 11 of Example 1 was replaced with a bisazo compound represented by the following structural formula (G-2). No. 22 was prepared and the copied images were evaluated in the same manner as in Example 2. Regarding the durability of repeated printing under high temperature and high humidity conditions, the contrast decreased from around 30,000 times and only images with a lot of fog were obtained. I couldn't.
以下e曳。The following e-hiki.
一一一ニシ
(G−2)
実施例3
ポリエステルフィルム上にアルミニウム箔をラミネート
して成る導電性支持体上に、塩化ビニル−酢酸ビニル−
無水マレイン酸共重合体、「エスレックM F −10
4(積水化学社製)より成る厚さ0.05μmの中間層
を設け、その上にキャリア輸送物質として下記構造式(
K −11)を6gとポリカーボネート樹脂[パンライ
トL−1250410gとを1.2−ジクロルエタン8
01Qに溶解した液を乾燥後の膜厚が15μmに成るよ
うに塗布して、キャリア輸送層を形成した。111 Nishi (G-2) Example 3 Vinyl chloride-vinyl acetate-
Maleic anhydride copolymer, “S-LEC MF-10
4 (manufactured by Sekisui Chemical Co., Ltd.) with a thickness of 0.05 μm was provided, and on top of that, the following structural formula (
6 g of K-11) and 410 g of polycarbonate resin [Panlite L-1250] and 8 g of 1,2-dichloroethane.
A carrier transport layer was formed by applying a solution dissolved in 01Q to a dry film thickness of 15 μm.
(K−11)
更にその上にキャリア発生物質A−5,A−8A−10
の2g、上記キャリア輸送物質1.5g及びポリカーボ
ネート樹脂[パンライトL−1250J 2gを1,2
−ジクロルエタン301gに加え、24時間ボールミル
で分散した液を塗布し、乾燥後の膜厚が4μmであるキ
ャリア発生層を設け、本発明の感光体試料No、23〜
25を作成した。(K-11) Furthermore, carrier generating substances A-5, A-8A-10
1.5 g of the above carrier transport substance and 2 g of polycarbonate resin [Panlite L-1250J]
- In addition to 301 g of dichloroethane, a solution dispersed in a ball mill for 24 hours was applied, and a carrier generation layer having a film thickness of 4 μm after drying was provided.
25 was created.
これらの感光体のそれぞれについて帯電極性を正帯電と
した他は実施例1と同様にして測定したところ第2表に
示す結果を得た。Each of these photoreceptors was measured in the same manner as in Example 1, except that the charging polarity was changed to positive, and the results shown in Table 2 were obtained.
以下余白
第2表
実施例4
キャリア発生層に用いるキャリア発生物質およびキャリ
ア輸送層に用いるキャリア輸送物質を第3表のように変
えたほかは、実施例1と同様にして感光体試料No、2
6〜43を作成した。Table 2 with blank space below Example 4 Photoreceptor samples No. 2
6 to 43 were created.
得られた感光体試料は、LED光源を装着したプリンタ
ーL P −3010(コニカ社製)の改造機を用い、
未露光部電位V□、露光部電位vLを求めて、感度の評
価とした。結果を第3表に示す。The obtained photoreceptor sample was processed using a modified printer LP-3010 (manufactured by Konica) equipped with an LED light source.
The potential V□ of the unexposed area and the potential VL of the exposed area were determined to evaluate the sensitivity. The results are shown in Table 3.
比較例3
キャリア発生層に用いる化合物およびキャリア輸送層に
用いる化合物を第3表のように代えたほかは、実施例4
と同様にして感光体試料N o、44を作成した。Comparative Example 3 Example 4 except that the compounds used in the carrier generation layer and the compounds used in the carrier transport layer were changed as shown in Table 3.
Photoreceptor sample No. 44 was prepared in the same manner as above.
得られた感光体について、実施例4と同様にして、感度
の評価を行なった。結果を第3表に示す。The sensitivity of the obtained photoreceptor was evaluated in the same manner as in Example 4. The results are shown in Table 3.
第3表
9G−1は比較例1で用いた化合物
に−12
に−13
に−14
に−15
に−16
に−17
に−18
に−20
以上の実施例、比較例の結果から明らかなように本発明
の感光体試料は比較用感光体試料に比べ、安定性、感度
、耐久性、広範なキャリア輸送物質との組合せ等におい
て著しく優れたものであることがわかった。Table 3 9G-1 shows that the compound used in Comparative Example 1 had -12 to -13 to -14 to -15 to -16 to -17 to -18 to -20 which is clear from the results of the above examples and comparative examples. As can be seen, the photoreceptor samples of the present invention were found to be significantly superior to the comparative photoreceptor samples in terms of stability, sensitivity, durability, compatibility with a wide range of carrier transport substances, and the like.
Claims (1)
ゾ化合物を含有する感光層を有することを特徴とする電
子写真感光体。 一般式[ I ] ▲数式、化学式、表等があります▼ [式中Cpはそれぞれ独立にフェノール性水酸基を有す
るカプラー残基を表わし、R^1、R^2、R^3、R
^4及びR^5はそれぞれ置換基を表わし、m^1及び
m^3はそれぞれ0〜5の整数を表わし、m^2及びm
^4はそれぞれ0〜4の整数を表わし、m^3は0〜3
の整数を表わし、l及びnはそれぞれ0又は1を表わす
。][Scope of Claims] An electrophotographic photoreceptor comprising a photosensitive layer containing a bisazo compound represented by the following general formula [I] on a conductive support. General formula [I] ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [In the formula, Cp each independently represents a coupler residue having a phenolic hydroxyl group, R^1, R^2, R^3, R
^4 and R^5 each represent a substituent, m^1 and m^3 each represent an integer of 0 to 5, m^2 and m
Each ^4 represents an integer from 0 to 4, and m^3 represents an integer from 0 to 3.
, and l and n each represent 0 or 1. ]
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP27007890A JPH04146446A (en) | 1990-10-08 | 1990-10-08 | Electrophotographic sensitive body |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP27007890A JPH04146446A (en) | 1990-10-08 | 1990-10-08 | Electrophotographic sensitive body |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH04146446A true JPH04146446A (en) | 1992-05-20 |
Family
ID=17481225
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP27007890A Pending JPH04146446A (en) | 1990-10-08 | 1990-10-08 | Electrophotographic sensitive body |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH04146446A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109790132A (en) * | 2016-07-07 | 2019-05-21 | 保土谷化学工业株式会社 | Compound and organic electroluminescent device with benzoxazole ring structure |
-
1990
- 1990-10-08 JP JP27007890A patent/JPH04146446A/en active Pending
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109790132A (en) * | 2016-07-07 | 2019-05-21 | 保土谷化学工业株式会社 | Compound and organic electroluminescent device with benzoxazole ring structure |
EP3483148A4 (en) * | 2016-07-07 | 2020-04-15 | Hodogaya Chemical Co., Ltd. | Compound having benzazole ring structure and organic electroluminescent element |
CN109790132B (en) * | 2016-07-07 | 2024-03-05 | 保土谷化学工业株式会社 | Compound having benzoxazole ring structure and organic electroluminescent element |
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