JPH01201670A - Electrophotographic sensitive body - Google Patents
Electrophotographic sensitive bodyInfo
- Publication number
- JPH01201670A JPH01201670A JP2696688A JP2696688A JPH01201670A JP H01201670 A JPH01201670 A JP H01201670A JP 2696688 A JP2696688 A JP 2696688A JP 2696688 A JP2696688 A JP 2696688A JP H01201670 A JPH01201670 A JP H01201670A
- Authority
- JP
- Japan
- Prior art keywords
- group
- carrier
- substance
- layer
- photosensitive layer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 125000005843 halogen group Chemical group 0.000 claims abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 2
- 108091008695 photoreceptors Proteins 0.000 claims description 49
- 239000000126 substance Substances 0.000 claims description 49
- -1 bisazo compound Chemical class 0.000 claims description 45
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 5
- 125000002837 carbocyclic group Chemical group 0.000 claims description 4
- 230000035945 sensitivity Effects 0.000 abstract description 11
- 239000000463 material Substances 0.000 abstract description 9
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 5
- 125000001424 substituent group Chemical group 0.000 abstract description 5
- 125000003277 amino group Chemical group 0.000 abstract description 4
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 abstract description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 abstract description 2
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 abstract description 2
- 125000004429 atom Chemical group 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 239000000049 pigment Substances 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 65
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 25
- 150000001875 compounds Chemical class 0.000 description 24
- 229920005989 resin Polymers 0.000 description 15
- 239000011347 resin Substances 0.000 description 15
- 239000011230 binding agent Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 239000003963 antioxidant agent Substances 0.000 description 6
- 235000006708 antioxidants Nutrition 0.000 description 6
- 239000002612 dispersion medium Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000002800 charge carrier Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000011241 protective layer Substances 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 230000018044 dehydration Effects 0.000 description 3
- 238000006297 dehydration reaction Methods 0.000 description 3
- 230000006866 deterioration Effects 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 3
- 229920005668 polycarbonate resin Polymers 0.000 description 3
- 239000004431 polycarbonate resin Substances 0.000 description 3
- 229910052711 selenium Inorganic materials 0.000 description 3
- 239000011669 selenium Substances 0.000 description 3
- 239000002356 single layer Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- WUPHOULIZUERAE-UHFFFAOYSA-N 3-(oxolan-2-yl)propanoic acid Chemical compound OC(=O)CCC1CCCO1 WUPHOULIZUERAE-UHFFFAOYSA-N 0.000 description 2
- SPVVMXMTSODFPU-UHFFFAOYSA-N 3-methyl-n-(3-methylbutyl)butan-1-amine Chemical compound CC(C)CCNCCC(C)C SPVVMXMTSODFPU-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 2
- 229910052980 cadmium sulfide Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 229920006026 co-polymeric resin Polymers 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- YDSWCNNOKPMOTP-UHFFFAOYSA-N mellitic acid Chemical compound OC(=O)C1=C(C(O)=O)C(C(O)=O)=C(C(O)=O)C(C(O)=O)=C1C(O)=O YDSWCNNOKPMOTP-UHFFFAOYSA-N 0.000 description 2
- JACMPVXHEARCBO-UHFFFAOYSA-N n-pentylpentan-1-amine Chemical compound CCCCCNCCCCC JACMPVXHEARCBO-UHFFFAOYSA-N 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920001225 polyester resin Polymers 0.000 description 2
- 239000004645 polyester resin Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- WGVKWNUPNGFDFJ-DQCZWYHMSA-N β-tocopherol Chemical compound OC1=CC(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C WGVKWNUPNGFDFJ-DQCZWYHMSA-N 0.000 description 2
- GVJHHUAWPYXKBD-IEOSBIPESA-N (R)-alpha-Tocopherol Natural products OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
- UKDOTCFNLHHKOF-FGRDZWBJSA-N (z)-1-chloroprop-1-ene;(z)-1,2-dichloroethene Chemical group C\C=C/Cl.Cl\C=C/Cl UKDOTCFNLHHKOF-FGRDZWBJSA-N 0.000 description 1
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- NMNSBFYYVHREEE-UHFFFAOYSA-N 1,2-dinitroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C([N+]([O-])=O)C([N+](=O)[O-])=CC=C3C(=O)C2=C1 NMNSBFYYVHREEE-UHFFFAOYSA-N 0.000 description 1
- IZUKQUVSCNEFMJ-UHFFFAOYSA-N 1,2-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1[N+]([O-])=O IZUKQUVSCNEFMJ-UHFFFAOYSA-N 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- XVMIKRZPDSXBTP-UHFFFAOYSA-N 1,3-dibromobutan-2-one Chemical compound CC(Br)C(=O)CBr XVMIKRZPDSXBTP-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-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
- HJRJRUMKQCMYDL-UHFFFAOYSA-N 1-chloro-2,4,6-trinitrobenzene Chemical compound [O-][N+](=O)C1=CC([N+]([O-])=O)=C(Cl)C([N+]([O-])=O)=C1 HJRJRUMKQCMYDL-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
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 1
- KWLXMHPDSIQHDF-UHFFFAOYSA-N 10-methyl-n-(10-methylundecyl)undecan-1-amine Chemical compound CC(C)CCCCCCCCCNCCCCCCCCCC(C)C KWLXMHPDSIQHDF-UHFFFAOYSA-N 0.000 description 1
- SPSPIUSUWPLVKD-UHFFFAOYSA-N 2,3-dibutyl-6-methylphenol Chemical compound CCCCC1=CC=C(C)C(O)=C1CCCC SPSPIUSUWPLVKD-UHFFFAOYSA-N 0.000 description 1
- BIEFDNUEROKZRA-UHFFFAOYSA-N 2-(2-phenylethenyl)aniline Chemical class NC1=CC=CC=C1C=CC1=CC=CC=C1 BIEFDNUEROKZRA-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- FEXBEKLLSUWSIM-UHFFFAOYSA-N 2-Butyl-4-methylphenol Chemical compound CCCCC1=CC(C)=CC=C1O FEXBEKLLSUWSIM-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- RPLZABPTIRAIOB-UHFFFAOYSA-N 2-chloro-5-dodecylbenzene-1,4-diol Chemical compound CCCCCCCCCCCCC1=CC(O)=C(Cl)C=C1O RPLZABPTIRAIOB-UHFFFAOYSA-N 0.000 description 1
- ZNQOWAYHQGMKBF-UHFFFAOYSA-N 2-dodecylbenzene-1,4-diol Chemical compound CCCCCCCCCCCCC1=CC(O)=CC=C1O ZNQOWAYHQGMKBF-UHFFFAOYSA-N 0.000 description 1
- BSJQLOWJGYMBFP-UHFFFAOYSA-N 2-methyl-5-(2,4,4-trimethylpentan-2-yl)benzene-1,4-diol Chemical compound CC1=CC(O)=C(C(C)(C)CC(C)(C)C)C=C1O BSJQLOWJGYMBFP-UHFFFAOYSA-N 0.000 description 1
- KCXONTAHNOAWQJ-UHFFFAOYSA-N 2-methyl-5-octadec-2-enylbenzene-1,4-diol Chemical compound CCCCCCCCCCCCCCCC=CCC1=CC(O)=C(C)C=C1O KCXONTAHNOAWQJ-UHFFFAOYSA-N 0.000 description 1
- NJBCRXCAPCODGX-UHFFFAOYSA-N 2-methyl-n-(2-methylpropyl)propan-1-amine Chemical compound CC(C)CNCC(C)C NJBCRXCAPCODGX-UHFFFAOYSA-N 0.000 description 1
- HXIQYSLFEXIOAV-UHFFFAOYSA-N 2-tert-butyl-4-(5-tert-butyl-4-hydroxy-2-methylphenyl)sulfanyl-5-methylphenol Chemical compound CC1=CC(O)=C(C(C)(C)C)C=C1SC1=CC(C(C)(C)C)=C(O)C=C1C HXIQYSLFEXIOAV-UHFFFAOYSA-N 0.000 description 1
- XOUQAVYLRNOXDO-UHFFFAOYSA-N 2-tert-butyl-5-methylphenol Chemical compound CC1=CC=C(C(C)(C)C)C(O)=C1 XOUQAVYLRNOXDO-UHFFFAOYSA-N 0.000 description 1
- FKVNZFAMXGMPOU-UHFFFAOYSA-N 23204-36-6 Chemical compound C1=CC2=CC(O)=CC(C(=O)OC3=O)=C2C3=C1 FKVNZFAMXGMPOU-UHFFFAOYSA-N 0.000 description 1
- VYWYYJYRVSBHJQ-UHFFFAOYSA-N 3,5-dinitrobenzoic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 VYWYYJYRVSBHJQ-UHFFFAOYSA-N 0.000 description 1
- ITUYMTWJWYTELW-UHFFFAOYSA-N 4-chloroiminocyclohexa-2,5-dien-1-one Chemical compound ClN=C1C=CC(=O)C=C1 ITUYMTWJWYTELW-UHFFFAOYSA-N 0.000 description 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- WWDQROFMFKRUIF-UHFFFAOYSA-N 4-methyl-n-(4-methylpentyl)pentan-1-amine Chemical compound CC(C)CCCNCCCC(C)C WWDQROFMFKRUIF-UHFFFAOYSA-N 0.000 description 1
- ROFZMKDROVBLNY-UHFFFAOYSA-N 4-nitro-2-benzofuran-1,3-dione Chemical compound [O-][N+](=O)C1=CC=CC2=C1C(=O)OC2=O ROFZMKDROVBLNY-UHFFFAOYSA-N 0.000 description 1
- OTLNPYWUJOZPPA-UHFFFAOYSA-N 4-nitrobenzoic acid Chemical compound OC(=O)C1=CC=C([N+]([O-])=O)C=C1 OTLNPYWUJOZPPA-UHFFFAOYSA-N 0.000 description 1
- NKJIFDNZPGLLSH-UHFFFAOYSA-N 4-nitrobenzonitrile Chemical compound [O-][N+](=O)C1=CC=C(C#N)C=C1 NKJIFDNZPGLLSH-UHFFFAOYSA-N 0.000 description 1
- MMVIDXVHQANYAE-UHFFFAOYSA-N 5-nitro-2-benzofuran-1,3-dione Chemical compound [O-][N+](=O)C1=CC=C2C(=O)OC(=O)C2=C1 MMVIDXVHQANYAE-UHFFFAOYSA-N 0.000 description 1
- MEXUTNIFSHFQRG-UHFFFAOYSA-N 6,7,12,13-tetrahydro-5h-indolo[2,3-a]pyrrolo[3,4-c]carbazol-5-one Chemical compound C12=C3C=CC=C[C]3NC2=C2NC3=CC=C[CH]C3=C2C2=C1C(=O)NC2 MEXUTNIFSHFQRG-UHFFFAOYSA-N 0.000 description 1
- JCKVKMNRMJLTGO-UHFFFAOYSA-N 6-methyl-n-(6-methylheptyl)heptan-1-amine Chemical compound CC(C)CCCCCNCCCCCC(C)C JCKVKMNRMJLTGO-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 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
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- SBPMVSRBSQIBLG-UHFFFAOYSA-N C(CCC)(C1=C(C(=CC(=C1)C)CCCC)O)C1=C(C(=CC(=C1)C)CCCC)O Chemical compound C(CCC)(C1=C(C(=CC(=C1)C)CCCC)O)C1=C(C(=CC(=C1)C)CCCC)O SBPMVSRBSQIBLG-UHFFFAOYSA-N 0.000 description 1
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 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
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000004419 Panlite Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
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- 150000002461 imidazolidines Chemical class 0.000 description 1
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- 150000002484 inorganic compounds Chemical class 0.000 description 1
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
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- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
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- 150000003219 pyrazolines Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
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- 125000005504 styryl group Chemical group 0.000 description 1
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- 239000011593 sulfur Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
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- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
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- AUHHYELHRWCWEZ-UHFFFAOYSA-N tetrachlorophthalic anhydride Chemical compound ClC1=C(Cl)C(Cl)=C2C(=O)OC(=O)C2=C1Cl AUHHYELHRWCWEZ-UHFFFAOYSA-N 0.000 description 1
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- 229910001887 tin oxide Inorganic materials 0.000 description 1
- AOBORMOPSGHCAX-DGHZZKTQSA-N tocofersolan Chemical compound OCCOC(=O)CCC(=O)OC1=C(C)C(C)=C2O[C@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C AOBORMOPSGHCAX-DGHZZKTQSA-N 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- CFAVHELRAWFONI-UHFFFAOYSA-N tris(2,4-dibutylphenyl) phosphite Chemical compound CCCCC1=CC(CCCC)=CC=C1OP(OC=1C(=CC(CCCC)=CC=1)CCCC)OC1=CC=C(CCCC)C=C1CCCC CFAVHELRAWFONI-UHFFFAOYSA-N 0.000 description 1
- IUURMAINMLIZMX-UHFFFAOYSA-N tris(2-nonylphenyl)phosphane Chemical compound CCCCCCCCCC1=CC=CC=C1P(C=1C(=CC=CC=1)CCCCCCCCC)C1=CC=CC=C1CCCCCCCCC IUURMAINMLIZMX-UHFFFAOYSA-N 0.000 description 1
- OBNYHQVOFITVOZ-UHFFFAOYSA-N tris[2,3-di(nonyl)phenyl]phosphane Chemical compound CCCCCCCCCC1=CC=CC(P(C=2C(=C(CCCCCCCCC)C=CC=2)CCCCCCCCC)C=2C(=C(CCCCCCCCC)C=CC=2)CCCCCCCCC)=C1CCCCCCCCC OBNYHQVOFITVOZ-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
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Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
- G03G5/0664—Dyes
- G03G5/0675—Azo dyes
- G03G5/0679—Disazo dyes
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Photoreceptors In Electrophotography (AREA)
Abstract
Description
【発明の詳細な説明】
［産業上の利用分野］
本発明は電子写真感光体に関し、詳しくは特定のビスア
ゾ化合物を含有する感光層を有する電子写真感光体に関
する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to an electrophotographic photoreceptor, and more particularly to an electrophotographic photoreceptor having a photosensitive layer containing a specific 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、装造上も難しく、また熱や指紋等が原因とな
り結晶化し、感光体としての性能が劣化してしまう。[Prior Art] Conventionally, inorganic photoreceptors 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 assemble, and it also crystallizes due to heat, fingerprints, etc., resulting in deterioration of its performance as a photoreceptor.
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。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なわれている。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−ドリニトロー９−フルオレノンを
含有する感光層を有する有機感光体の記載がある。しか
しこの感光体は、感度及び耐久性において必ずしも満足
できるものではない。このような欠点を改良するために
キャリア発生様能とキャリア輸送様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。このようないわゆる機能分離型の
感光体は、それぞれの材料を広い範囲から選択すること
ができ、任意の性能を有する感光体を比較的容易に作成
し得ることから多くの研究がなされてきた。In order to overcome these drawbacks of inorganic photoreceptors, research and development have been actively conducted in recent years on organic photoreceptors having photosensitive layers containing various organic photoconductive compounds as main components. For example, Japanese Patent Publication No. 50-10496 describes an organic photoreceptor having a photosensitive layer containing poly-N-vinylcarbazole and 2,4,7-dolinitro-9-fluorenone. However, this photoreceptor is not necessarily satisfactory in sensitivity and durability. In order to improve these drawbacks, attempts have been made to develop organic photoreceptors with higher performance by assigning carrier generation-like abilities and carrier-transporting abilities to different substances. Many studies have been conducted on such so-called function-separated type photoreceptors because each material can be selected from a wide range and a photoreceptor having arbitrary performance can be produced relatively easily.
［発明が解決しようとする問題点］
上記のような機能分離型の感光体において、そのキャリ
ア発生物質として、数多くの化合物が提案されている。[Problems to be Solved by the Invention] Many compounds have been proposed as carrier-generating substances in the functionally separated type photoreceptor as described above.
無機化合物をキャリア発生物質どして用いる例としては
、例えば、特公昭４３−１６１９８号に記載された無定
形セレンがあり、これは有機光導電性化合物と組合せて
使用されるが、無定形セレンからなるキャリア発生層は
熱により結晶化して感光体としての特性が劣化してしま
うという欠点は改良されていない。An example of using an inorganic compound as a carrier-generating substance is amorphous selenium, which is described in Japanese Patent Publication No. 16198/1983, and is used in combination with an organic photoconductive compound. The disadvantage that the carrier generation layer consisting of the above crystallizes due to heat and deteriorates the characteristics as a photoreceptor has not been improved.
また有機染料や有機顔料をキャリア発生物質として用い
る電子写真感光体も数多く提案されている。例えば、ビ
スアゾ化合物を感光層中に含有する電子写真感光体とし
て、特開昭５４−２２８３４号、同５５−７３０５７号
、同５５−１１７１５１号、同５６−４６２３７号等が
すでに公知である。しかしこれらのビスアゾ化合物は感
度、残留電位あるいは、繰返し使用時の安定性の特性に
おいて、必ずしも満足し得るものではなく、また、キャ
リア輸送物質の選択範囲も限定されるなど、電子写真プ
ロセスの幅広い要求を十分満足させるものではない。Furthermore, many electrophotographic photoreceptors using organic dyes or organic pigments as carrier-generating substances have been proposed. For example, as electrophotographic photoreceptors containing a bisazo compound in the photosensitive layer, JP-A-54-22834, JP-A-55-73057, JP-A-55-117151, and JP-A-56-46237 are already known. However, these bisazo compounds do not necessarily satisfy the characteristics of sensitivity, residual potential, or stability during repeated use, and the range of selection of carrier transport materials is also limited, which makes them difficult to meet the wide demands of electrophotographic processes. It does not fully satisfy.
［発明の目的］
本発明の目的はキャリア発生能に優れた特定のビスアゾ
化合物を含有する電子写真感光体を提供することにある
。[Object of the Invention] 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（、
更に繰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.
［問題点を解決するための手段］
本発明者等は、以上の目的を達成すべく鋭意研究を重ね
た結果、特定のビスアゾ化合物が電子写真感光体の浸れ
た有効成分として勤ぎ得る事を見出し、本発明を完成し
たものである。[Means for Solving the Problems] As a result of intensive research to achieve the above object, the present inventors have found that a specific bisazo compound can serve as an active ingredient in an electrophotographic photoreceptor. The heading completes the invention.
すなわち、本発明の上記目的は、導電性支持体上に下記
−殺人［Ｉ］で表わされる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を用いることにより達成す
ることができる。That is, the above object of the present invention can be achieved by using an electrophotographic photoreceptor having a photosensitive layer containing a bisazo compound represented by the following formula [I] on a conductive support.
−殺人［Ｉ］
・Ｚ・
［Ｒ＋おＪ：びＲ２は、それぞれ、水素原子、ハロゲン
原子、アルキル基、アルコキシ基、ニトロ基、シアン基
又はヒドロキシ基を表わす。但しＲ１およびＲ２は、そ
れぞれ、同−又は異なっていてもよい。-Murder [I] -Z- [R+J: and R2 each represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a nitro group, a cyan group or a hydroxy group. However, R1 and R2 may be the same or different.
Ｚは炭素環式芳香族環又は複素環式芳香族環を形成する
のに必要な原子群を表わす。Z represents an atomic group necessary to form a carbocyclic aromatic ring or a heterocyclic aromatic ring.
ｍおよびｎはそれぞれ１，２又は３の整数を表わす。］
［発明の具体的構成］
一般式［ＩＥにおけるＲ１およびＲ２のハロゲン原子と
しては塩素原子、臭素原子、フッ素原子、沃素原子を挙
げることができるが、このうち塩素原子又は臭素原子が
好ましい。m and n each represent an integer of 1, 2 or 3. ] [Specific Structure of the Invention] The halogen atoms for R1 and R2 in the general formula [IE include a chlorine atom, a bromine atom, a fluorine atom, and an iodine atom, among which a chlorine atom or a bromine atom is preferred.
Ｒ１およびＲ２のアルキル基としては炭素原子数１から
４のアルキル基が好ましく、例えばメチル基、エチル基
、イソプロピル基、ｔ−ブチル基、トリフルオロメチル
基等が好ましい。The alkyl group for R1 and R2 is preferably an alkyl group having 1 to 4 carbon atoms, such as a methyl group, an ethyl group, an isopropyl group, a t-butyl group, or a trifluoromethyl group.
Ｒ１およびＲ２のアルコキシ基としては、炭素原子数１
〜４のアルコキシ基が好ましく、例えばメトキシ基、エ
トキシ基、イソプロポキシ基、ｔ−ブトキシ基、２−り
Ｏロエトキシ基等を挙げることができる。As the alkoxy group of R1 and R2, the number of carbon atoms is 1
-4 alkoxy groups are preferred, such as methoxy, ethoxy, isopropoxy, t-butoxy, 2-O-loethoxy and the like.
Ｒ１およびＲ２の基のうち、好ましい基は水素原子、ハ
ロゲン原子、アルキル基、アルコキシ基である。Among the groups R1 and R2, preferred groups are a hydrogen atom, a halogen atom, an alkyl group, and an alkoxy group.
Ｚは、炭素環式芳香族環又は複素環式芳香族環を形成す
るのに必要な原子群を表わすが、このような原子群によ
って形成される炭素環式芳香族環の例としては置換・未
置換のベンゼン環、ナフタレン環等が、また、複素環式
芳香族環の例としては、置換・未置換のジベンゾチオフ
ェン環、カルバゾール環等がそれぞれ挙げられる。これ
らの芳香族環は、置換基を有することができる。置換基
としては、例えば、ハロゲン原子、アミン基、アルキル
基、ヒドロキシ基等を挙げることができる。Z represents an atomic group necessary to form a carbocyclic aromatic ring or a heterocyclic aromatic ring, and examples of a carbocyclic aromatic ring formed by such an atomic group include substitutions, Examples of the heterocyclic aromatic ring include unsubstituted benzene rings and naphthalene rings, and examples of the heterocyclic aromatic rings include substituted and unsubstituted dibenzothiophene rings and carbazole rings. These aromatic rings can have substituents. Examples of the substituent include a halogen atom, an amine group, an alkyl group, and a hydroxy group.
前記−殺人［ＩＥにおいて、■およびｎは１゜２又は３
の整数を表わすが、好ましくはＩ＝１、ｎ −１である
。Said - Murder [in IE, ■ and n are 1°2 or 3
, preferably I=1, n −1.
−又はｎは共に同じ整数であっても、異なる整数であっ
てもよい。ｌ又はｎが２以上のときは、Ｒ１およびＲ２
は、いずれも同じ又は異なる基であっても差し支えない
。- or n may both be the same integer or different integers. When l or n is 2 or more, R1 and R2
may be the same or different groups.
一般式［ＩＥで表わされる本発明のビスアゾ化合物は、
好ましくは、下記−殺人［ＩＡ］、［ＩＢ］ 、 ［
ＩＣ］ 、 ［Ｉ０］ 、 ［ＩＥ コ 、−殺
人［ＩＡ］
○
一般式［Ｉ Ｂｌ
一般式［ＩＣ］
Ｒニ
一般式［ＩＤ］
Ｒ；
〇
一般式［ＩＥ］
−叙ＲＬ ｌ ｒ 」
前記−殺人［ＩＡ］〜［ＩＧ］において、Ｒ１およびＲ
’２ は、前記−殺人［Ｉ］のＲ１および殺人［Ｉ］
の２と同義である。The bisazo compound of the present invention represented by the general formula [IE]
Preferably - Murder [IA], [IB], [
IC], [I0], [IE Ko, - Murder [IA] ○ General formula [I Bl General formula [IC] R ni General formula [ID] R; In murder [IA] to [IG], R1 and R
'2 is R1 of the above-murder [I] and murder [I]
It is synonymous with 2.
次に本発明の前記−殺人［Ｉ］で示されるビスアゾ化合
物の具体例について述べるがこれによって本発明のビス
アゾ化合物が限定されるものではないｄ
、 −１本発明の前記−殺人［Ｉ
］で表されるビスアゾ化合物は、公知の方法により容易
に合成することができる。Next, specific examples of the bisazo compound represented by the above-mentioned -murder [I] of the present invention will be described, but the bisazo compound of the present invention is not limited thereto.
, -1 The above-mentioned of the present invention - Murder [I
] The bisazo compound represented by can be easily synthesized by a known method.
合成例１（−殺人［２Ｂ］で示される
例示化合物Ｎ０１１の合成）
３．６−ジアミツー９−フルオレノン２．１０ｇ（０，
０２モル）を塩酸１０ｄ、水２０１ｇに分散し、５℃以
下に保ちつつ、亜硝酸ナトリウム１．４ｇ（０，０２モ
ル）を水５１βに溶解した溶液を滴下した。同温度でさ
らに１時間撹拌をつづけた後、不用物を濾過除去し、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。Synthesis Example 1 (Synthesis of exemplified compound N011 represented by -murder [2B]) 2.10 g of 3.6-diamitwo-9-fluorenone (0,
0.02 mol) was dispersed in 10 d of hydrochloric acid and 201 g of water, and while keeping the temperature below 5° C., a solution of 1.4 g (0.02 mol) of sodium nitrite dissolved in 51 β of water was added dropwise. After stirring for another hour at the same temperature, unnecessary materials were removed by filtration, and 4.6 g of ammonium hexafluorophosphate was added to the filtrate in 501 J2 of water.
A solution dissolved in was added.
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） １００１ｇに溶解した。The precipitated tetrazonium salt was collected by filtration and dissolved in 1001 g of N,N-dimethylformamide (DMF).
５℃以下に保ちながら、無水３−ヒドロキシ−１゜８−
ナフタル酸とオルト−フェニレンジアミンを脱水縮合し
て得られる化合物Ｃｐ −Ａ ５．７ｇ（０，０２モル
）をＤＭＦ２００ｄに溶解した溶液を滴下した。Anhydrous 3-hydroxy-1°8- while keeping the temperature below 5°C.
A solution of 5.7 g (0.02 mol) of a compound Cp-A obtained by dehydration condensation of naphthalic acid and ortho-phenylenediamine dissolved in 200 d of DMF was added dropwise.
ひきつづき５℃以下に保ちながら、トリエタノールアミ
ン６０ （０，０４モル）を、ＤＭＦ３０１Ｒに溶解
したものを滴下し、５℃以下で１時間、室温で４時間撹
拌した。反応後、析出晶を濾取し、ＤＭＦ洗浄、水洗し
て乾燥し、目的物６．２１ｇを得た。Subsequently, while keeping the temperature below 5°C, a solution of triethanolamine 60 (0.04 mol) in DMF301R 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 6.21 g of the desired product.
計算値：Ｃ−７３，１％、１ｌ＝３．０％、Ｎ＝１３．
９％実測値：Ｃ＝７１．５％、Ｈ＝３．６％Ｊｌ−１４
．．５％（ＣｐＡ）
合成例２（−殺人［ＩＡ］で示される
例示化合物Ｎｏ、６５の合成）
３．６−ジアミツー２．７−ジクロル−９−フルオレノ
ン２．７９（１（０，０２モル）を塩酸Ｉｏｔａ。Calculated values: C-73, 1%, 1l=3.0%, N=13.
9% actual value: C = 71.5%, H = 3.6% Jl-14
．． ．． 5% (CpA) Synthesis Example 2 (Synthesis of Exemplified Compound No. 65 represented by -murder [IA]) 3.6-Diami2.7-dichloro-9-fluorenone 2.79 (1 (0.02 mol) Iota of hydrochloric acid.
水２０１ｆｆｉに分散し、５℃以下に保ちつつ、亜硝酸
ナトリウム１．４９ （０，０２モル）を水５１Ｑに
溶解した溶液を滴下した。同温度で、さらに１時間撹拌
をつづけた後、不用物を濾過除去し、濾液に六フフ化燐
酸アンモニウム４．６９を水５０ｖ１２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）１００１βに溶解し
た。５℃以下に保ちながら、無水３−ヒトＯキシー１．
８−ナフタル酸と３．４−ジアミントルエンを脱水縮合
して得られる化合物Ｃｐ−Ｂ Ｓ、９８ｇ（０，０２モ
ル）をＤＭＦ２００１２に溶解した溶液を滴下した。The mixture was dispersed in 201ffi of water, and a solution of 1.49 (0.02 mol) of sodium nitrite dissolved in 51Q of water was added dropwise while keeping the temperature below 5°C. After continuing stirring at the same temperature for an additional hour, unnecessary materials were removed by filtration, and to the filtrate was added a solution of 4.69 ml of ammonium hexafufluoride phosphate dissolved in 50 ml of water. The precipitated tetrazonium salt was collected by filtration, and N,N
-Dissolved in dimethylformamide (DMF) 1001β. 1. Anhydrous 3-human oxygen while keeping the temperature below 5°C.
A solution prepared by dissolving 98 g (0.02 mol) of a compound Cp-BS obtained by dehydration condensation of 8-naphthalic acid and 3,4-diaminetoluene in DMF20012 was added dropwise.
ひきつづき５℃以下に保ちながら、トリエタノールアミ
ン５１７ （０，０４モル）をＤ Ｍ Ｆ ３０ ｖ
２に溶解したものを滴下し、５℃以下で１時間、室温で
４時間撹拌した。反応後、析出晶を濾取し、ＤＭＦ洗浄
、水洗して乾燥し、目的物６．２１ｇを得た。Triethanolamine 517 (0.04 mol) was added to DMF 30 v while continuing to maintain the temperature below 5°C.
2 was added dropwise to the mixture, and the mixture was stirred at 5° C. or lower 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 6.21 g of the desired product.
計算値；Ｃ−６７，９％、 Ｈ−２，８９％、Ｎ＝１２
．４％実測値：Ｃ−６５，２％、 Ｈ＝ ２．９９％、
Ｎ−１４，１％以下余白
（Ｃｐ−Ｂ）
本発明の他の化合物も、前記合成例と同様に、３．６−
シアミツ−置換、未置換−９−フルオレノンを用いてテ
トラゾ体を作り、次いで無水３−ヒドロキシ−１，８ナ
フタル酸と芳香族ジアミンを脱水縮合して得られる化合
物Ｃｐ−Ｃ等を反応させて作ることができる。Calculated values: C-67, 9%, H-2, 89%, N=12
．． 4% actual value: C-65, 2%, H = 2.99%,
N-14, 1% or less margin (Cp-B) Other compounds of the present invention are also 3.6-
A tetrazo compound is prepared using cyamitsu-substituted or unsubstituted-9-fluorenone, and then a compound Cp-C obtained by dehydration condensation of 3-hydroxy-1,8 naphthalic anhydride and an aromatic diamine is reacted. be able to.
式中７は、アルキル基、ハロゲン原子、ニトロ基、アミ
ノ基、ジアルキルアミノ基およびヒドロキシ基から選ば
れる１以上の置換基で置換されていてもよい芳香族炭化
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
基を示す。In the formula, 7 represents a divalent group of an aromatic hydrocarbon or a nitrogen atom which may be substituted with one or more substituents selected from an alkyl group, a halogen atom, a nitro group, an amino group, a dialkylamino group, and a hydroxy group. Indicates a divalent group of a heterocyclic ring contained within the ring.
本発明の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。本発明のビスアゾ化合物は、その浸れた
キレ９フ発生能を利用して、これをキャリア発生物質と
して用い、これと組合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。前記礪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
の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、キャリア輸送物質を含むキャリア輸送層
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 of the present invention has excellent photoconductivity,
The electrophotographic photoreceptor of the present invention can be manufactured by providing a photosensitive layer in which the photoreceptor is dispersed in a binder on a conductive support. The bisazo compound of the present invention is a so-called functionally separated type, by making use of its ability to generate sharpness, using it as a carrier-generating substance, and using a carrier-transporting substance that can effectively act in combination with the bisazo compound. It can be used as a photoreceptor. The functional separation type photoreceptor may be a mixed and dispersed type of both of the above substances, but it may include a carrier generation layer containing a carrier generation substance made of the bisazo compound of the present invention, and a carrier transport layer containing a carrier transport substance. It is more preferable to use a laminated type photoreceptor in which these are laminated.
本発明の電子写真感光体は、例えば、第１図に示すよう
に支持体１（導電性支持体またはシート上に導電層を設
けたもの）上に、キャリア発生物質と必要に応じてバイ
ンダ樹脂を含有するキャリア発生層２を下層とし、キャ
リア輸送物質とバインダ樹脂を含有するキャリア輸送層
３を上層とする機能分離型の積層構成の感光層４を設け
たもの、第２図に示すように支持体１上にキャリア輸送
層３を下層とし、キャリア発生層２を上層とする積層構
成の感光層４を設けたもの、および第３図に示すように
支持体１上にキャリア発生物質、キャリア輸送物質およ
びバインダ樹脂を含有する単層構成の感光層４を設けた
もの、等が挙げられる。The electrophotographic photoreceptor of the present invention, for example, as shown in FIG. As shown in FIG. 2, a photosensitive layer 4 is provided with a functionally separated laminated structure in which a carrier generation layer 2 containing a carrier-transporting substance and a binder resin is a lower layer, and a carrier-transporting layer 3 containing a carrier-transporting substance and a binder resin is an upper layer. A photosensitive layer 4 having a laminated structure including a carrier transport layer 3 as a lower layer and a carrier generation layer 2 as an upper layer is provided on a support 1, and a carrier generation substance and a carrier are provided on the support 1 as shown in FIG. Examples include those provided with a single-layer photosensitive layer 4 containing a transport substance and a binder resin.
尚、積層構成の感光層の場合キャリア発生層は入射光ｍ
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充分な膜
厚の範囲でできる限り薄膜層とすることが好ましい。In addition, in the case of a photosensitive layer with a laminated structure, the carrier generation layer absorbs the incident light m
Most of the charge carriers are absorbed by the charge generation layer to generate many charge generation carriers, and photocarriers are generated in order to inject the generated charge carriers into the carrier transport layer without being deactivated by recombination or trapping. It is preferable to make the layer as thin as possible within a range of thickness sufficient to achieve this.
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主層から注入さ
れた電荷キャリアを受は取るとともにこれらの電荷キャ
リアを表面まで輸送できる機能を有している。In addition, the carrier transport layer is electrically connected to the carrier generation layer described above, and has the function of receiving and taking charge carriers injected from the charge generation layer in the presence of an electric field and transporting these charge carriers to the surface. have.
またｌｉ層構成の敦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な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レリアの輸送
に寄与するものである。In addition, in a functional separation type photoreceptor with a Li 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 Generated substances also contribute to the transport of Chirelia.
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もＪ：い。Furthermore, the carrier generation layer may contain both the carrier generation substance and part of the carrier transport substance.
いずれのを構成においても、第７図乃至第９図で示され
るように感光層（４）の上に保護層（６）を設けてもよ
く、さらには第４図乃至第６図に示すように支持体（１
）と感光層（４）の間にバリア機能と接着性をもつ下引
層（中間層）（５）を設けてもよい。In either structure, a protective layer (6) may be provided on the photosensitive layer (4) as shown in FIGS. 7 to 9, or a protective layer (6) may be provided on the photosensitive layer (4) as shown in FIGS. to the support (1
) and the photosensitive layer (4) may be provided with a subbing layer (intermediate layer) (5) having a barrier function and adhesive properties.
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、例えば塩
化ビニル−酢酸ビニル共重合体樹脂、塩化ビニル−酢酸
ビニル−無水マレイン酸共重合体樹脂等の絶縁性樹脂の
他、ポリ−Ｎ−ビニルカルバゾール等の高分子有機半η
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,
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, such as vinyl chloride-vinyl acetate copolymers In addition to insulating resins such as composite resins and vinyl chloride-vinyl acetate-maleic anhydride copolymer resins, polymeric organic semi-η such as poly-N-vinylcarbazole
One example is the body.
又、本発明の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７Ｊ［Ｌ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
。Further, organic amines can be added to the photosensitive layer of the present invention for the purpose of improving the carrier-generating function of the carrier-generating substance, and it is particularly preferable to add a secondary amine.
かかる２級アミンとしては、例えばジメチルアミン、ジ
エチルアミン、ジ−ｎプロピルアミン、ジ−イソプロピ
ルアミン、ジ−ｎブチルアミン、ジ−イソブチルアミン
、ジ−ｎアミルアミン、ジ−イソアミルアミン、ジ−ｎ
ヘキシルアミン、ジ−イソヘキシルアミン、ジ−ｎペン
チルアミン、ジ−イソペンチルアミン、ジ−ｎオクチル
アミン、ジ−イソオクチルアミン、シーｎノニルアミン
、ジルイソノニルアミン、ジ−ｎデシルアミン、ジ−イ
ソデシルアミン、ジ−ｎモノデシルアミン、ジ−イソモ
ノデシルアミン、ジ−ｎドデシルアミン、ジ−イソドデ
シルアミン等を挙げることができる。Such secondary amines include, for example, dimethylamine, diethylamine, di-n propylamine, di-isopropylamine, di-n butylamine, di-isobutylamine, di-n amylamine, di-isoamylamine, di-n
Hexylamine, di-isohexylamine, di-n-pentylamine, di-isopentylamine, di-n-octylamine, di-isooctylamine, di-n-nonylamine, dilisononylamine, di-n-decylamine, di-iso Examples include decylamine, di-n-monodecylamine, di-isomonodecylamine, di-n-dodecylamine, and di-isododecylamine.
又かかる有機アミン類の添加ｊとしては、キャリア発生
物質に対して該キレリア発生物質の１倍以下、好ましく
は０．２倍〜０．００５倍の範囲のモル数とするのがよ
い。The amount of organic amines to be added is preferably 1 times or less, preferably 0.2 to 0.005 times the amount of the chyrelia-generating substance relative to the carrier-generating substance.
又、本発明の感光層においては、オゾン劣化防止の目的
で酸化防止剤を添加することができる。Further, in the photosensitive layer of the present invention, an antioxidant can be added for the purpose of preventing ozone deterioration.
かかる酸化防止剤の代表的具体例を以下に示すが、これ
に限定されるものではない。Typical examples of such antioxidants are shown below, but the invention is not limited thereto.
（Ｉ）群：ヒンダードフェノール類
ジブチルヒドロキシトルエン、２．２′−メチレンビス
（６−１−ブチル−４−メチルフェノール）、４．４’
−７チリデンビス（６−ｔ−ブチル−３−メチルフェノ
ール）、４．４’ −チオビス（６−ｔ−ブチル−３−
メチルフェノール）、２．２′−ブチリデンビス（６−
℃−ブチルー４−メチルフェノール）、α−トコフェロ
ール、β−トコフェロール、２．２．４−）−ツメチル
−６−ヒドロキシ−７−ｔ−ブチルクロマン、ペンタエ
リスチルテトラキス［３−（３，５−ジー【−ブチル−
４−ヒドロキシフェニル）プロピオネート］、２．２’
−チオジエチレンビス［３−（３゜５−ジ−ｔ−ブチ
ル−４−ヒドロキシフェニル）プロピオネート１．１．
６−ヘキサンジオールビス［３−（３，５−ジ−ｔ−ブ
チル−４−ヒドロキシフェニル）プロピオネート］、ブ
チルヒドロキシアニソール、ジブチルヒドロキシアニソ
ール、１−［２−（＜３．５−ジーｔｅｒｔ−ブチルー
４−ヒドロキシフェニル）プロピオニルオキシ）エチル
］ −４−［３−（３，５−ジーｔｅｒｔ−ブチルー４
−ヒドロキシフェニル）プロピオニルオキシ］−２，２
，６，６−チトラメチルビペリジルなど。Group (I): Hindered phenols dibutylhydroxytoluene, 2.2'-methylenebis(6-1-butyl-4-methylphenol), 4.4'
-7 thylidene bis(6-t-butyl-3-methylphenol), 4,4'-thiobis(6-t-butyl-3-
methylphenol), 2,2'-butylidene bis(6-
-butyl-4-methylphenol), α-tocopherol, β-tocopherol, 2.2.4-)-tumethyl-6-hydroxy-7-t-butylchroman, pentaerythyltetrakis [3-(3,5- G [-Butyl-
4-hydroxyphenyl)propionate], 2.2'
-thiodiethylenebis[3-(3°5-di-t-butyl-4-hydroxyphenyl)propionate 1.1.
6-hexanediol bis[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate], butylhydroxyanisole, dibutylhydroxyanisole, 1-[2-(<3.5-di-tert-butyl)propionate] 4-hydroxyphenyl)propionyloxy)ethyl] -4-[3-(3,5-di-tert-butyl-4
-hydroxyphenyl)propionyloxy]-2,2
, 6,6-titramethylbiperidyl and the like.
（ＩＩ）群：バラフエニレンジアミン類Ｎ−フェニル−
Ｎ′−イソプロピル−ｐ−フ工ニレンジアミン、Ｎ、Ｎ
’−ジー５ｅｃ−ブチル−ｐ−フェニレンジアミン、Ｎ
−フェニル−Ｎ−３ｅＣ−ブチル−ｐ−フェニレンジア
ミン、Ｎ。Group (II): Paraphenyl diamines N-phenyl-
N'-isopropyl-p-phenyl diamine, N,N
'-5ec-butyl-p-phenylenediamine, N
-Phenyl-N-3eC-butyl-p-phenylenediamine, N.
Ｎ′−ジイソプロピル−ｐ−フェニレンジアミン、Ｎ、
Ｎ’−ジメチル−Ｎ、Ｎ’−ジー℃−ブブルーｐ−フェ
ニレンジアミンなど。N'-diisopropyl-p-phenylenediamine, N,
N'-dimethyl-N, N'-diC-bublue p-phenylenediamine, and the like.
（ＩＩＩ）群：ハイドロキノン類
２．５−ジー［−オクチルハイドロキノン、２゜６−シ
ドデシルハイドロキノン、２−ドデシルハイドロキノン
、２−ドデシル−５−クロロハイドロキノン、２−ｔ−
オクチル−５−メチルハイドロキノン、２−（２−オク
タデセニル）−５−メチルハイドロキノンなど。Group (III): Hydroquinones 2.5-di[-octylhydroquinone, 2゜6-sidedecylhydroquinone, 2-dodecylhydroquinone, 2-dodecyl-5-chlorohydroquinone, 2-t-
Octyl-5-methylhydroquinone, 2-(2-octadecenyl)-5-methylhydroquinone, etc.
（ＩＶ）群：有機硫黄化合物類
ジラウリル−３，３′−チオジプロピオネート、ジステ
アリル−３，３′−チオジプロピオネート、タテトラデ
シル−３，３′−チオジプロピオネートなど。Group (IV): organic sulfur compounds dilauryl-3,3'-thiodipropionate, distearyl-3,3'-thiodipropionate, tatetradecyl-3,3'-thiodipropionate, etc.
（Ｖ）群：有機燐化合物類
トリフェニルホスフィン、トリ（ノニルフェニル）ホス
フィン、トリ（ジノニルフェニル）ホスフィン、トリク
レジルホスフィン、トリ（２，４−ジブチルフェノキシ
）ホスフィンなど。Group (V): Organic phosphorus compounds triphenylphosphine, tri(nonylphenyl)phosphine, tri(dinonylphenyl)phosphine, tricresylphosphine, tri(2,4-dibutylphenoxy)phosphine, etc.
これらの化合物はゴム、プラスチック、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重伶部に対して０．１〜１００重量部、好ましくは１
〜５０重母部、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
ミニウム、ニッケルなどの金属板、金属ドラム又は金属
箔、アルミニウム、酸化スズ、酸化インジウムなどを蒸
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 is a metal plate made of aluminum, nickel, etc., a metal drum or metal foil, a plastic film deposited with aluminum, tin oxide, indium oxide, etc., or paper coated with a conductive substance. , a film or drum of plastic or the like 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
発明のビスアゾ化合物を適当な分散媒又は溶媒に単独も
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、スプレー塗布、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 of the present invention described above in a suitable dispersion medium or solvent alone or together with a suitable binder resin, for example, by dip coating, spray coating, blade coating, etc. It can be provided by a method of coating on the support or subbing layer or carrier transport layer by roll coating or the like and drying it.
本発明のビスアゾ化合物はこれを例えばボールミル、サ
ンドミル等を用いて適当な粒径の微細粒子にしたのち、
分散媒中に分散することができる。The bisazo compound of the present invention is made into fine particles of an appropriate particle size using, for example, a ball mill or a sand mill.
It can be dispersed in a dispersion medium.
本発明の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。A ball mill, homomixer, sand mill, ultrasonic disperser, attritor, etc. are used for dispersing the bisazo compound of the present invention.
本発明の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、メチレンブロマイド、１，２−ジ
クロロエタン、ｓｙｍ−テトラクロロエタン、ｃｉｓ−
１，２−ジクロロエチレン、１．１．２−トリクロロエ
タン、１，１．１−トリクロロエタン、１．２−ジクロ
ロプロパン、クロロホルム、ブロモホルム、クロルベン
ゼン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及びこ
の誘導体、テ；へラヒドロフラン、１，４−ジオキサン
、フラン、ラルフラール等のエーテル、アセタール類、
ピリジンやｎ−ブチルアミン、ジエチルアミン、エチレ
ンジアミン、イソプロパツールアミン等のアミン類、Ｎ
、Ｎ−ジメチルホルムアミド等のアミド類等の窒素化合
物他に脂肪酸及びフェノール類、二硫化炭素やリン酸ト
リエチル等のイオウ、リン化合物等の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 of the present invention include hydrocarbons such as hexane, benzene, toluene, and xylene;
Methylene chloride, methylene bromide, 1,2-dichloroethane, sym-tetrachloroethane, cis-
Halogenated hydrocarbons such as 1,2-dichloroethylene, 1.1.2-trichloroethane, 1,1.1-trichloroethane, 1.2-dichloropropane, chloroform, bromoform, chlorobenzene, etc., ketones such as acetone, methyl ethyl ketone, cyclohexanone, etc. ethyl acetate,
Esters such as butyl acetate, methanol, ethanol,
Alcohols and derivatives thereof such as propatool, butanol, cyclohexanol, heptatool, ethylene glycol, methyl cellosolve, ethyl cellosolve, acetic acid cellosolve, ethers and acetals such as herahydrofuran, 1,4-dioxane, furan, and ralfural. kind,
Amines such as pyridine, n-butylamine, diethylamine, ethylenediamine, isopropanolamine, N
In addition to nitrogen compounds such as amides such as , N-dimethylformamide, one or more of fatty acids, phenols, 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
のバインダー：キャリア発生物買：キャリア輸送物質の
重母比はＯ〜１００： １〜５００： 。When the photoreceptor of the present invention has a laminated structure, the weight ratio of binder:carrier generating material:carrier transport material in the carrier generating layer is O~100:1~500:.
〜５００である。~500.
キャリア発生物質の含有割合がこれより少ないと光感度
が低く、残留電位の増加を招き、またこれより多いと暗
減衰及び受容電位が低下する。If the content of the carrier-generating substance is less than this, the photosensitivity will be low and the residual potential will increase, and if it is more than this, the dark decay and acceptance potential will decrease.
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.
また、キレリア輸送層は、キャリア輸送物質を適用な溶
媒又は分散媒に単独であるいは上述のバインダ樹脂と共
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。Further, the chyrelia transport layer can be formed by applying a carrier transport substance dissolved or dispersed in an appropriate solvent or dispersion medium alone or together with the above-mentioned binder resin, and drying. 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、
ピラゾリン誘導体、アミン銹導体、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 derivatives, amine conductors, 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トリア輸送物質としては光
照射時発生するボールの支持体側への輸送能力が優れて
いる外、前記本発明のビスアゾ化合物との組合せに好適
なものが好ましく用いられ、かかるキャリア輸送物質と
して好ましいものは、下記−殺人（Ａ）、（Ｂ）及び（
Ｃ）で表わされるものが挙げられる。The chitria transport substance used in the present invention is preferably one that has an excellent ability to transport balls generated during light irradiation to the support side, and is suitable for combination with the bisazo compound of the present invention, such that carrier transport Preferred substances are the following - murder (A), (B) and (
Examples include those represented by C).
一般式（Ａ）
但し、ＡＩ’ ｔ 、Ａｒ ２ 、ＡＩ’ ４ ハソｔ
ＬＰし研ｎ又は未置換のアリール基を表わし、Ａｒ３は
置換又は未置換のアリーレン基を表わし、Ｒ１は水素原
子、置換若しくは未置換のアルキル基、又は置換もしく
は未置換のアリール基を表わす。General formula (A) However, AI' t , Ar 2 , AI' 4 Hasot
LP represents an unsubstituted aryl group, Ar3 represents a substituted or unsubstituted arylene group, and R1 represents a hydrogen atom, a substituted or unsubstituted alkyl 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
の第３〜４頁及び同５８−１９８０４３号の第３〜６頁
に詳細に記載されている。Specific examples of such compounds are described in detail on pages 3 to 4 of JP-A-58-65440 and pages 3-6 of JP-A-58-198043.
一般式（Ｂ） 但し、Ｒ１は置換、未置換のアリール基、置換。General formula (B) However, R1 is a substituted or unsubstituted aryl group, or a substituted group.
未置換の複素環基であり、Ｒ２は水素原子、置換。It is an unsubstituted heterocyclic group, and R2 is a hydrogen atom and is substituted.
未置換のアルキル基、置換、未置換のアリール基を表わ
し、ｎは０．１又は２の整数を表わし、詳細には特開昭
５８−１３４６４２号及び同５８−１６６３５４号の公
報に記載されている。It represents an unsubstituted alkyl group, a substituted or unsubstituted aryl group, n represents an integer of 0.1 or 2, and is described in detail in Japanese Patent Application Laid-Open No. 58-134642 and No. 58-166354. There is.
一般式（Ｃ）
但し、Ｒ１は置換、未置換のアルキル基又は置換、未置
換のアリール基であり、Ｒ２は水素原子、ハロゲン原子
、置換、未、Ｈ換のアルキル基、置換。General formula (C) However, R1 is a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group, and R2 is a hydrogen atom, a halogen atom, a substituted, unsubstituted, or H-substituted alkyl group, or a substituted.
未置換のアルコキシ基、置換、未置換のアミン基、ヒド
ロキシ基であり、Ｒ３は置換、未買換のアリール基、置
換、未置換の複素環基を表わす。これらの化合物の合成
法及びその例示は特公昭５７−１４８７５０号公報に詳
細に記載されており、本発明に援用することができる。They are an unsubstituted alkoxy group, a substituted or unsubstituted amine group, or a hydroxy group, and R3 represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group. Synthesis methods for these compounds and their illustrations are described in detail in Japanese Patent Publication No. 148750/1983, which can be incorporated into the present invention.
本発明のその他の好ましいキャリア輸送物質としては、
特開昭５７−６７９４０号、同５９−１５２５２号、同
５７−１０１８４４号公報にそれぞれ記載されているヒ
ドラゾン化合物を挙げることができる。Other preferred carrier transport materials of the present invention include:
Examples include hydrazone compounds described in JP-A-57-67940, JP-A-59-15252, and JP-A-57-101844, respectively.
キャリア輸送層中のバインダ樹脂１００重量部当りキャ
リア輸送物質は２０〜２００重傷部が好ましく、特に好
ましくは３０〜１５０重量部である。The carrier transport material in the carrier transport layer is preferably 20 to 200 parts by weight, particularly preferably 30 to 150 parts by weight, per 100 parts by weight of the binder resin.
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、本発明の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のバインダー二本発明のビスア
ゾ化合物：キャリア輸送物質の割合は０〜１００：
１〜５００： 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
５〜３０μＩである。Further, in the case of a monolayer functionally separated type electrophotographic photoreceptor using the bisazo compound of the present invention, the ratio of the binder to the bisazo compound of the present invention:carrier transport substance is 0 to 100:
1 to 500: O to 500 is preferred, and the thickness of the photosensitive layer to be formed is preferably 5 to 50 μm, particularly preferably 5 to 30 μI.
本発明においてキャリア発生層には感度の向上、残留電
位乃至反復使用時の疲労低減等を目的として、一種又は
二種以上の電子受容性物質を含有せしめることができる
。In the present invention, the carrier generation layer may contain one or more electron-accepting substances for the purpose of improving sensitivity, reducing residual potential or fatigue during repeated use, etc.
ここに用いることのできる電子受容性物質としては、例
えば、無水コハク酸、無水マレイン酸、ジブロム無水マ
レイン酸、無水フタル酸、テトラクロル無水フタル酸、
テトラブロム無水フタル酸、３−ニトロ無水フタル酸、
４−ニトロ無水フタル酸、無水ピロメリット酸、無水メ
リット酸、テトラシアノエチレン、テトラシアノキノジ
メタン、Ｏ−ジニトロベンゼン、■−ジニトロベンゼン
、１．３．５−トリニトロベンゼン、パラニトロベンゾ
ニトリル、ピクリルクロライド、キノンクロルイミド、
クロラニル、ブルマニル、ジクロロジシアノバラベンゾ
キノン、アントラキノン、ジニトロアントラキノン、２
．７−シニトロフルオレノン、２．４．７−トリニトロ
フルオレノン、２゜４．５．７−テトラニトロフルオレ
ノン、９−フルオレニリデン［ジシアノメチレンマロノ
ジニトリル］、ポリニトロ−９−フルオレニリデン−［
ジシアノメチレンマロノジニトリル］、ピクリン酸、０
−ニトロ安息香酸、ｐ−ニトロ安息香酸、３．５−ジニ
トロ安息香酸、ペンタフルオロ安息香酸、５−ニトロサ
リチル酸、３，５−ジニ１−ロサリチル酸、フタル酸、
メリット酸、その他の電子親和力の大きい化合物を挙げ
ることができる。Examples of electron-accepting substances that can be used here include succinic anhydride, maleic anhydride, dibromaleic anhydride, phthalic anhydride, tetrachlorophthalic anhydride,
Tetrabromo phthalic anhydride, 3-nitro phthalic anhydride,
4-nitrophthalic anhydride, pyromellitic anhydride, mellitic anhydride, tetracyanoethylene, tetracyanoquinodimethane, O-dinitrobenzene, ■-dinitrobenzene, 1.3.5-trinitrobenzene, paranitrobenzonitrile, Picryl chloride, quinone chlorimide,
Chloranil, brumanil, dichlorodicyanobarabenzoquinone, anthraquinone, dinitroanthraquinone, 2
．． 7-sinitrofluorenone, 2.4.7-trinitrofluorenone, 2゜4.5.7-tetranitrofluorenone, 9-fluorenylidene [dicyanomethylenemalonodinitrile], polynitro-9-fluorenylidene-[
dicyanomethylenemalonodinitrile], picric acid, 0
-Nitrobenzoic acid, p-nitrobenzoic acid, 3,5-dinitrobenzoic acid, pentafluorobenzoic acid, 5-nitrosalicylic acid, 3,5-dini-1-rosalicylic acid, phthalic acid,
Examples include mellitic acid and other compounds with high electron affinity.
また、電子受容性物質の添加割合は、重量比で本発明の
ビスアゾ化合物：電子受容性物質＝ １００：０．０
１〜２００、好ましくは１００： ０．１〜１００で
ある。The addition ratio of the electron-accepting substance is bisazo compound of the present invention: electron-accepting substance = 100:0.0 by weight.
1 to 200, preferably 100:0.1 to 100.
この電子受容性物質はキャリア輸送層に添加してもよい
。かかる層への電子受容性物質の添加割合は重量比で全
キャリア輸送物質：電子受容性物質＝ １００： ０
．０１〜１００、好ましクハ１００： ０．１〜５０
である。This electron-accepting substance may be added to the carrier transport layer. The ratio of electron-accepting substances added to this layer is the following by weight: total carrier transport substance:electron-accepting substance=100:0
．． 01-100, preferably Kuha 100: 0.1-50
It is.
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.
本発明のビスアゾ化合物を含有する電子写真感光体は可
視光線、近赤外線の光線に良好に感応することができる
が、好ましくは約４００〜８５０μＩの間の波長に吸収
極大を有している。The electrophotographic photoreceptor containing the bisazo compound of the present invention can be sensitive to visible light and near-infrared light, but preferably has an absorption maximum at a wavelength of about 400 to 850 μI.
このような波長を有する光源としてはハロゲンランプ、
蛍光灯、タングステンランプやアルゴンレーザー、ヘリ
ウム−ネオンレーザ−等の気体レーザー及び半導体レー
ザー等が一般的に用いられる。Examples of light sources with such wavelengths include halogen lamps,
Fluorescent lamps, tungsten lamps, gas lasers such as argon lasers, helium-neon lasers, and semiconductor lasers are commonly used.
本発明の電子写真感光体は以上のような構成であって、
後述する実施例からも明らかなように、帯電特性、感度
特性画像形成特性に優れており、特に繰返し使用したと
きにも疲労劣化が少なく、耐用性が優れたものである。The electrophotographic photoreceptor of the present invention has the above structure,
As is clear from the Examples described below, it has excellent charging characteristics, sensitivity characteristics, and image forming characteristics, and especially shows little fatigue deterioration even when used repeatedly, and has excellent durability.
［実施例］
以下、本発明を実施例によって具体的に説明するが、こ
れにより本発明の実７Ｊｌ！ｉ態様が限定されるもので
はない。[Examples] Hereinafter, the present invention will be specifically explained with reference to Examples, which demonstrate the practical aspects of the present invention. The i-mode is not limited.
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−１０Ｊ
（Ｉ水化学社製）よりなる厚さ０．０５μｍの中間層を
設け、その上に一般式［ＩＤ］で示される例示化合物Ｎ
ｏ、 ２を２ｇとポリカーボネート樹脂「パンライト
Ｌ−１２５０Ｊ （密入化成社製）２（］とを］１．
２−ジクロロエタン１１０に加え、ボールミルで１２時
間分散した。Example 1 Vinyl chloride-vinyl acetate-
Maleic anhydride copolymer [S-LEC MF-10J
(manufactured by I-Sui Kagaku Co., Ltd.) with a thickness of 0.05 μm, and on top of that an exemplified compound N represented by the general formula [ID]
o, 2 g of 2 and polycarbonate resin "Panlite L-1250J (manufactured by Hitsuiri Kasei Co., Ltd.) 2 (])" 1.
The mixture was added to 110 g of 2-dichloroethane and dispersed in a ball mill for 12 hours.
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、更にその上に、キャリア
輸送層として、下記構造式（ＣＴ−１）６ｇとポリカー
ボネート樹脂「パンライトし−１２５０」１０ｇを１．
２−ジクロロエタン８０奴に溶解した液を乾燥後の膜厚
が１５μｍになるように塗布して、キャリア輸送層を形
成し、本発明の感光体を作成した。This dispersion was applied to a dry film thickness of 0.5 μm to form a carrier generation layer, and on top of that, 6 g of the following structural formula (CT-1) and polycarbonate resin “Pan” were applied as a carrier transport layer. Light-1250" 10g 1.
A carrier transport layer was formed by applying a solution dissolved in 80 μm of 2-dichloroethane so that the film thickness after drying was 15 μm, thereby producing a photoreceptor of the present invention.
（ＣＴ−１）
ＣＨ＋ｎ
以上のようにして得られた感光体を■用ロ電気製作所製
ＥＰＡ−８１００型静電紙試験礪械を用いて、以下の特
性評価を行なった。帯電圧−６ＫＶで５秒間帯電した後
、５秒間暗放置し、次いで感光体表面での照度が３５１
ｔｌＸ−Ｓｅｃになるようにハロゲンランプ光を照射
して、表面電位を半分に減衰させるのに要する露光口（
半減露光ｆｆ１）Ｅ１／２を求めた。また３ Ｑ Ｑｕ
ｘ−ｓｅｃの露光量で露光した後の表面電位（残留電位
）ＶＲを求めた。更に同様の測定を１００回繰り返して
行った。結果は第１表に示す通りである、
比較例１
キャリア発生物質として下記ビスアゾ化合物（ＣＧ−１
）を用いた他は、実施例１と同様にしくＣＧ−１）
この比較用感光体について、実施例１と同様にして測定
を行なっｌこところ、第１表に示す結果を得た。(CT-1) CH+n The photoreceptor obtained as described above was subjected to the following characteristic evaluation using an EPA-8100 type electrostatic paper testing machine manufactured by Roden Seisakusho. After being charged for 5 seconds with a charging voltage of -6KV, it was left in the dark for 5 seconds, and then the illuminance on the photoreceptor surface was 351.
The exposure aperture (
Half-exposure ff1) E1/2 was determined. Also 3 Q Qu
The surface potential (residual potential) VR after exposure with an exposure amount of x-sec was determined. Further, similar measurements were repeated 100 times. The results are shown in Table 1. Comparative Example 1 The following bisazo compound (CG-1) was used as a carrier generating substance.
CG-1) This comparative photoreceptor was measured in the same manner as in Example 1, and the results shown in Table 1 were obtained.
第１表
以上の結果から明らかなように、本発明の感光体は、比
較用感光体に比べ、感度、残留電位及び繰り返しの安定
性にＪ５いて極めて優れたものである。As is clear from the results in Table 1 and above, the photoreceptor of the present invention is extremely superior in sensitivity, residual potential, and repetition stability (J5) compared to the comparative photoreceptor.
実茄例２〜４
：ｌ（・リア発生物質として一般式［ＩＡ］で示される
例示化合物Ｎｏ、７５、一般式［ＩＣ］で示される例示
化合物Ｎｏ、１９、一般式［ＩＣ］で示される例示化合
物Ｎ０．２９をそれぞれに用い、キャリア輸送物質とし
て、それぞれ下記化合物を用い、その他は実施例１と同
様にして、本発明の感光体を作成し、同様の測定を行な
ったところ、第２表に示す結果を得た。Practical examples 2 to 4: l(・Exemplified compound No. 75 represented by the general formula [IA] as a rear-generating substance, Exemplified compound No. 19 represented by the general formula [IC], Represented by the general formula [IC] A photoreceptor of the present invention was prepared in the same manner as in Example 1, using Exemplified Compound No. The results shown in the table were obtained.
（ＣＴ−２）
（ＣＴ−３）
（ＣＴ−４）
第２表
以上の結果から、本発明のビスアゾ化合物をキャリア発
生物質として用いた電子写真感光体は、実施例１ど同様
に感度が高く、残留電位も低く、かつ繰り返し特性に張
れていることｈ（分かｇ。(CT-2) (CT-3) (CT-4) From the results in Table 2 and above, the electrophotographic photoreceptor using the bisazo compound of the present invention as a carrier generating substance has high sensitivity as in Example 1. , the residual potential is low, and the repeatability is good (h (min. g).
実施例５
直径６０１Ｉｌｌ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−１０Ｊ （積木化学社製）より成る厚さ０．
０５２１ｍの中間層を設け、その上に一般式［ＩＢ］の
構造を有する例示化合物Ｎｏ、５２、一般式［ＩＡ］の
４７．１迄を右する例示化合物Ｎｏ。Example 5 On the surface of an aluminum drum having a diameter of 601 Ill, a 0.0 mm thick film made of vinyl chloride-vinyl acetate-maleic anhydride copolymer "S-LEC MF-10J (manufactured by Block Chemical Co., Ltd.)" was coated.
0521m intermediate layer is provided thereon, exemplified compound No. 52 has the structure of general formula [IB], and exemplified compound No. 52 has the structure of general formula [IA] up to 47.1.
９３、一般式［ＩＡ］の構造をＮ する例示化合物ＮＯ
，１０６の２ｇとポリエステル樹脂「バイロン２００Ｊ
（東洋紡社製）２（＋とを１．２−９９０日エタン
１００１１２に混合し、ボールミル分散機で２４時間分
散した分１１（液を乾燥後の膜厚が０．６μｍになるよ
うにしてｔＪ イｔｉ Ｌ／、キレリア発生層を形成し
た。93, Exemplary compound NO in which the structure of general formula [IA] is N
, 2g of 106 and polyester resin "Byron 200J"
(Manufactured by Toyobo Co., Ltd.) 1.2-990 days Mix ethane 100112 with ethane 100112 and disperse it for 24 hours using a ball mill disperser. Iti L/, a chyrelia generation layer was formed.
さらにこの上に、下記化合物（ＣＴ−５）３０ｇとポリ
カーボネー１〜１″１４脂「ニーピロン３−１ｏｏｏ、
１（三菱瓦斯化学社製）５０９とを１，２−ジクロロエ
タン４００ｄに溶解し、乾燥後の膜厚が１８μ田になる
ように塗布してキレリア輸送層を形成し、感光体をつく
った。Furthermore, on top of this, 30 g of the following compound (CT-5) and polycarbonate 1-1" 14 fat "Niepiron 3-1ooo,
1 (manufactured by Mitsubishi Gas Chemical Co., Ltd.) 509 was dissolved in 400 d of 1,2-dichloroethane and coated to form a chyrelia transport layer so that the film thickness after drying was 18 μm, thereby producing a photoreceptor.
（ＣＴ−５）
このようにして作成した感光体を電子写真複写ＩＲｒ
Ｕ −Ｂ ｉｘ１５５０Ｍ ＲＪ （Ｋ ｏｎｉｃａ社
製）の改造機に装着し、画像を複写したところコントラ
ス１〜が高く、原画に忠実でかつ鮮明な複写画像を得た
。(CT-5) Electrophotographic reproduction IRr of the photoreceptor thus prepared
When it was attached to a modified U-Bix1550M RJ (manufactured by Konica) and an image was copied, it had a high contrast of 1 to 1 and a clear copy image that was faithful to the original was obtained.
また、これは１０．０００回繰り返しても変ることはな
かった。Moreover, this did not change even after repeating 10,000 times.
比較例２
実施例５における例示化合物を下記構造式（ＣＧ−２）
で表されるビスアゾ化合物に代えた他は、実施例５と同
様にしてドラム状の比較用感光体を作成し、実施例５と
同様にして複写画像を評価したところ、カブリが多い画
像しか１ｑられなかった。又、複写を繰り返していくに
従い、複写画像のコントラストが低下し、１０，０００
回繰り返すとほとんど複写画像は１ｑられなかった。Comparative Example 2 The exemplified compound in Example 5 was represented by the following structural formula (CG-2).
A drum-shaped comparative photoreceptor was prepared in the same manner as in Example 5, except that the bisazo compound represented by I couldn't. Also, as copying is repeated, the contrast of the copied image decreases, and
After repeating this process several times, almost no copies were made.
（ＣＧ−２）(CG-2)
第１図〜第９図はそれぞれ本発明の感光体の層橘成につ
いて示す断面図であって図中の１〜６はそれぞれ以下の
事を表わす。1 to 9 are cross-sectional views showing the layer structure of the photoreceptor of the present invention, and 1 to 6 in the figures represent the following, respectively.
Claims (3)
ビスアゾ化合物を含有する感光層を有することを特徴と
する電子写真感光体。 一般式［ I ］ ▲数式、化学式、表等があります▼ ［Ｒ＿１およびＲ＿２は、それぞれ、水素原子、ハロゲ
ン原子、アルキル基、アルコキシ基、ニトロ基、シアノ
基又はヒドロキシ基を表わす、但しＲ＿１およびＲ＿２
は、それぞれ、同一又は異なつていてもよい。 Ｚは炭素環式芳香族環又は複素環式芳香族環を形成する
のに必要な原子群を表わす。 ｍおよびｎはそれぞれ１、２又は３の整数を表わす。］(1) An electrophotographic photoreceptor comprising a photosensitive layer containing a bisazo compound represented by the following general formula [I] on a conductive support. General formula [I] ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [R_1 and R_2 each represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a nitro group, a cyano group, or a hydroxy group, provided that R_1 and R_2
may be the same or different. Z represents an atomic group necessary to form a carbocyclic aromatic ring or a heterocyclic aromatic ring. m and n each represent an integer of 1, 2 or 3. ]
質とを含有し、当該キャリア発生物質が前記一般式［
I ］で表わされるビスアゾ化合物であることを特徴とす
る請求項（１）記載の電子写真感光体。(2) The photosensitive layer contains a carrier-generating substance and a carrier-transporting substance, and the carrier-generating substance has the general formula [
The electrophotographic photoreceptor according to claim (1), which is a bisazo compound represented by I].
ア発生層と、キャリア輸送物質を含有するキャリア輸送
層との積層体で構成されていることを特徴とする請求項
（１）又は（２）記載の電子写真感光体。(3) Claim (1) or (2) characterized in that the photosensitive layer is constituted by a laminate of a carrier generation layer containing a carrier generation substance and a carrier transport layer containing a carrier transport substance. The electrophotographic photoreceptor described above.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2696688A JPH01201670A (en) | 1988-02-08 | 1988-02-08 | Electrophotographic sensitive body |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2696688A JPH01201670A (en) | 1988-02-08 | 1988-02-08 | Electrophotographic sensitive body |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH01201670A true JPH01201670A (en) | 1989-08-14 |
Family
ID=12207898
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2696688A Pending JPH01201670A (en) | 1988-02-08 | 1988-02-08 | Electrophotographic sensitive body |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01201670A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5488601A (en) * | 1992-10-26 | 1996-01-30 | Dai Nippon Printing Co., Ltd. | Photoelectric sensor, information recording system, and information recording method |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57176055A (en) * | 1981-04-21 | 1982-10-29 | Mitsubishi Chem Ind Ltd | Electrophotographic receptor |
| JPS60196772A (en) * | 1984-03-19 | 1985-10-05 | Konishiroku Photo Ind Co Ltd | Photosensitive body |
| JPS6325660A (en) * | 1986-07-18 | 1988-02-03 | Toyo Ink Mfg Co Ltd | Electrophotographic sensitive body |
-
1988
- 1988-02-08 JP JP2696688A patent/JPH01201670A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57176055A (en) * | 1981-04-21 | 1982-10-29 | Mitsubishi Chem Ind Ltd | Electrophotographic receptor |
| JPS60196772A (en) * | 1984-03-19 | 1985-10-05 | Konishiroku Photo Ind Co Ltd | Photosensitive body |
| JPS6325660A (en) * | 1986-07-18 | 1988-02-03 | Toyo Ink Mfg Co Ltd | Electrophotographic sensitive body |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5488601A (en) * | 1992-10-26 | 1996-01-30 | Dai Nippon Printing Co., Ltd. | Photoelectric sensor, information recording system, and information recording method |
| US5629920A (en) * | 1992-10-26 | 1997-05-13 | Dai Nippon Printing Co., Ltd. | Photoelectric sensor, information recording system, and information recording method |
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