JPH01142647A - Electrophotographic sensitive body - Google Patents
Electrophotographic sensitive bodyInfo
- Publication number
- JPH01142647A JPH01142647A JP62301862A JP30186287A JPH01142647A JP H01142647 A JPH01142647 A JP H01142647A JP 62301862 A JP62301862 A JP 62301862A JP 30186287 A JP30186287 A JP 30186287A JP H01142647 A JPH01142647 A JP H01142647A
- Authority
- JP
- Japan
- Prior art keywords
- photosensitive layer
- photoreceptor
- compound represented
- layer
- compounds
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000463 material Substances 0.000 claims abstract description 58
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims description 54
- 108091008695 photoreceptors Proteins 0.000 claims description 54
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 235000010290 biphenyl Nutrition 0.000 claims description 6
- 239000004305 biphenyl Substances 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 claims description 5
- SJHHDDDGXWOYOE-UHFFFAOYSA-N oxytitamium phthalocyanine Chemical compound [Ti+2]=O.C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 SJHHDDDGXWOYOE-UHFFFAOYSA-N 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 229920005989 resin Polymers 0.000 abstract description 31
- 239000011347 resin Substances 0.000 abstract description 31
- 239000011230 binding agent Substances 0.000 abstract description 26
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 abstract description 11
- 230000035945 sensitivity Effects 0.000 abstract description 11
- 230000000694 effects Effects 0.000 abstract description 4
- 230000005684 electric field Effects 0.000 abstract description 2
- 239000000203 mixture Substances 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 70
- 230000032258 transport Effects 0.000 description 25
- 238000006243 chemical reaction Methods 0.000 description 13
- -1 methoxy, ethoxy, propoxy, isopropoxy, butoxy Chemical group 0.000 description 13
- 239000002356 single layer Substances 0.000 description 13
- 238000000034 method Methods 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 10
- 239000011248 coating agent Substances 0.000 description 8
- 238000000576 coating method Methods 0.000 description 8
- 239000006185 dispersion Substances 0.000 description 8
- 229910052782 aluminium Inorganic materials 0.000 description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 238000001035 drying Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000002904 solvent Substances 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
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 206010034972 Photosensitivity reaction Diseases 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 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
- 238000010438 heat treatment Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 230000036211 photosensitivity Effects 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 229920002433 Vinyl chloride-vinyl acetate copolymer Polymers 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000007796 conventional method Methods 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
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000011241 protective layer Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- JFJWVJAVVIQZRT-UHFFFAOYSA-N 2-phenyl-1,3-dihydropyrazole Chemical class C1C=CNN1C1=CC=CC=C1 JFJWVJAVVIQZRT-UHFFFAOYSA-N 0.000 description 1
- GEKJEMDSKURVLI-UHFFFAOYSA-N 3,4-dibromofuran-2,5-dione Chemical compound BrC1=C(Br)C(=O)OC1=O GEKJEMDSKURVLI-UHFFFAOYSA-N 0.000 description 1
- FTJHOZUVOADALY-UHFFFAOYSA-N 4-(1,3-dihydropyrazol-2-yl)-N,N-dimethylaniline Chemical compound CN(C1=CC=C(C=C1)N1NC=CC1)C FTJHOZUVOADALY-UHFFFAOYSA-N 0.000 description 1
- YGBCLRRWZQSURU-UHFFFAOYSA-N 4-[(diphenylhydrazinylidene)methyl]-n,n-diethylaniline Chemical compound C1=CC(N(CC)CC)=CC=C1C=NN(C=1C=CC=CC=1)C1=CC=CC=C1 YGBCLRRWZQSURU-UHFFFAOYSA-N 0.000 description 1
- FAPXNOXKLZJBMT-UHFFFAOYSA-N 4-[5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazol-2-yl]-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1C1=NN=C(C=2C=CC(=CC=2)N(C)C)O1 FAPXNOXKLZJBMT-UHFFFAOYSA-N 0.000 description 1
- XYPMAZCBFKBIFK-UHFFFAOYSA-N 9,10-dinitroanthracene Chemical compound C1=CC=C2C([N+](=O)[O-])=C(C=CC=C3)C3=C([N+]([O-])=O)C2=C1 XYPMAZCBFKBIFK-UHFFFAOYSA-N 0.000 description 1
- SDDLEVPIDBLVHC-UHFFFAOYSA-N Bisphenol Z Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)CCCCC1 SDDLEVPIDBLVHC-UHFFFAOYSA-N 0.000 description 1
- 229910001369 Brass Inorganic materials 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000004709 Chlorinated polyethylene Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000004641 Diallyl-phthalate Substances 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 235000000177 Indigofera tinctoria Nutrition 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004419 Panlite Substances 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical class N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- HXGDTGSAIMULJN-UHFFFAOYSA-N acetnaphthylene Natural products C1=CC(C=C2)=C3C2=CC=CC3=C1 HXGDTGSAIMULJN-UHFFFAOYSA-N 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- CECABOMBVQNBEC-UHFFFAOYSA-K aluminium iodide Chemical compound I[Al](I)I CECABOMBVQNBEC-UHFFFAOYSA-K 0.000 description 1
- HUVXQFBFIFIDDU-UHFFFAOYSA-N aluminum phthalocyanine Chemical compound [Al+3].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 HUVXQFBFIFIDDU-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021417 amorphous silicon Inorganic materials 0.000 description 1
- PGEHNUUBUQTUJB-UHFFFAOYSA-N anthanthrone Chemical class C1=CC=C2C(=O)C3=CC=C4C=CC=C5C(=O)C6=CC=C1C2=C6C3=C54 PGEHNUUBUQTUJB-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 1
- 239000010951 brass Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
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- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
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- 238000005947 deacylation reaction Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
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- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
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- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
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- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- 239000007789 gas Substances 0.000 description 1
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- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
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- 150000008282 halocarbons Chemical class 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 229940097275 indigo Drugs 0.000 description 1
- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Chemical class N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 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
- 150000002475 indoles Chemical class 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229920000554 ionomer Polymers 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- XHNQXIBDPQINOF-UHFFFAOYSA-N n-(9h-carbazol-1-yl)fluoren-9-imine Chemical compound C12=CC=CC=C2C2=CC=CC=C2C1=NC1=CC=CC2=C1NC1=CC=CC=C12 XHNQXIBDPQINOF-UHFFFAOYSA-N 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 150000002916 oxazoles Chemical class 0.000 description 1
- YRZZLAGRKZIJJI-UHFFFAOYSA-N oxyvanadium phthalocyanine Chemical compound [V+2]=O.C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 YRZZLAGRKZIJJI-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000002080 perylenyl group Chemical class C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920002382 photo conductive polymer Polymers 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical class C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229920001909 styrene-acrylic polymer Polymers 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 230000003746 surface roughness Effects 0.000 description 1
- 239000012756 surface treatment agent Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- NLDYACGHTUPAQU-UHFFFAOYSA-N tetracyanoethylene Chemical group N#CC(C#N)=C(C#N)C#N NLDYACGHTUPAQU-UHFFFAOYSA-N 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 150000004961 triphenylmethanes Chemical class 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
- 239000010937 tungsten Substances 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
- G03G5/0601—Acyclic or carbocyclic compounds
- G03G5/0612—Acyclic or carbocyclic compounds containing nitrogen
- G03G5/0614—Amines
- G03G5/06142—Amines arylamine
- G03G5/06144—Amines arylamine diamine
- G03G5/061443—Amines arylamine diamine benzidine
Abstract
Description
【発明の詳細な説明】
〈産業上の利用分野〉
本発明は、複写機などの画像形成装置において好適に使
用される電子写真用感光体に関する。DETAILED DESCRIPTION OF THE INVENTION <Industrial Application Field> The present invention relates to an electrophotographic photoreceptor suitably used in an image forming apparatus such as a copying machine.
〈従来の技術と発明が解決しようとする問題点〉近年、
複写機などの画像形成装置における電子写真用感光体と
して、機能設計の自由度が大きな感光体、中でも光照射
により電荷を発生する電荷発生材料と、発生した電荷を
輸送する電荷輸送材料とを含有する感光層、例えば、電
荷発生材料と電荷輸送材料と結着樹脂とを含有する単層
型感光層や、上記電荷発生材料を含有する電荷発生層と
、電荷輸送材料と結着樹脂とを含有する電荷輸送層とが
積層された積層型感光層を備えた機能分離型電子写真用
感光体が提案されている。<Problems to be solved by conventional technology and inventions> In recent years,
As an electrophotographic photoreceptor in image forming devices such as copying machines, this photoreceptor has a high degree of freedom in functional design, and includes a charge-generating material that generates charges when irradiated with light and a charge-transporting material that transports the generated charges. For example, a single-layer photosensitive layer containing a charge generating material, a charge transporting material, and a binder resin, or a charge generating layer containing the above charge generating material, a charge transporting material, and a binder resin. A functionally separated electrophotographic photoreceptor has been proposed, which includes a laminated photosensitive layer in which a charge transport layer and a charge transport layer are laminated.
また、電子写真用感光体を用いて複写画像を形成する場
合、カールソンプロセスが広く利用されている。このカ
ールソンプロセスは、コロナ放電により感光体を均一に
帯電させる帯電工程と、帯電した感光体に原稿像を露光
し、原稿像に対応した静電潜像を形成する露光工程と、
静電潜像をトナーを含有する現像剤で現像し、トナー像
を形成する現像工程と、トナー像を紙などの基材に転写
する転写工程と、基材に転写されたトナー像を定着させ
る定着工程と、転写工程の後、感光体上に残留するトナ
ーを除去するクリーニング工程とを基本工程として含ん
でおり、上記カールソンプロセスにおいて高品質の画像
を形成するには、電子写真用感光体が、帯電特性および
感光特性に優れるとともに露光後の残留電位が低いこと
が要求される。Further, when forming a copy image using an electrophotographic photoreceptor, the Carlson process is widely used. This Carlson process consists of a charging process in which a photoreceptor is uniformly charged by corona discharge, an exposure process in which an original image is exposed to the charged photoreceptor to form an electrostatic latent image corresponding to the original image.
A development process in which an electrostatic latent image is developed with a developer containing toner to form a toner image, a transfer process in which the toner image is transferred to a base material such as paper, and a toner image transferred to the base material is fixed. The basic steps include a fixing process and a cleaning process to remove toner remaining on the photoreceptor after the transfer process. In order to form high-quality images in the Carlson process, the electrophotographic photoreceptor must be , they are required to have excellent charging properties and photosensitive properties, and to have a low residual potential after exposure.
一方、上記機能分離型電子写真用感光体においては、電
荷発生材料および電荷輸送材料の特性が感光体の電気的
特性、感光特性に大きく影響し、上記各材料の特性が十
分でないと、感光体の電気的特性および感光特性が低下
し、複写画像の品質が低下する。On the other hand, in the functionally separated electrophotographic photoreceptor, the characteristics of the charge generating material and the charge transporting material greatly affect the electrical characteristics and photosensitive characteristics of the photoreceptor, and if the characteristics of each of the above materials are insufficient, the photoreceptor The electrical and photosensitive properties of the photosensitive material deteriorate, resulting in a reduction in the quality of the reproduced image.
上記の点に鑑み、電荷輸送材料としてベンジジン誘導体
、例えば、4.4’−ビス[N−フェニル−N−(3−
メチルフェニル)アミノコシフェニル、4,4′−ビス
[N、N−ジ(4−メチルフェニル)アミノ]−2,2
’ −ジメチルジフェニル、4.4′−ビス[N、N−
ジ(4−メチルフェニル)アミノ]−3,3’ −ジメ
チルジフェニル等が提案されている(特開昭57−14
4558号公報、特開昭61−62038号公報、米国
特許第4047948号明細書、米国特許第45364
57号明細書、特開昭61−124949公報、特開昭
81−134354公報、特開昭61−134355公
報、特開昭82−112164公報参照)。In view of the above points, benzidine derivatives, such as 4,4'-bis[N-phenyl-N-(3-
methylphenyl)aminococyphenyl, 4,4'-bis[N,N-di(4-methylphenyl)amino]-2,2
' -dimethyldiphenyl, 4,4'-bis[N,N-
di(4-methylphenyl)amino]-3,3'-dimethyldiphenyl, etc. have been proposed (Japanese Patent Application Laid-Open No. 57-14
No. 4558, JP-A-61-62038, US Pat. No. 4,047,948, US Pat. No. 45364
57 specification, JP-A-61-124949, JP-A-81-134354, JP-A-61-134355, JP-A-82-112164).
上記ベンジジン誘導体を含有する感光層を備えた感光体
は、他の電荷輸送材料を含有する感光体と比較して、一
般に電気的特性および感光特性に優れている。A photoreceptor provided with a photosensitive layer containing the above-mentioned benzidine derivative generally has superior electrical properties and photosensitive properties compared to photoreceptors containing other charge transport materials.
しかしながら、上記ベンジジン誘導体は、結着樹脂との
相溶性が十分でなく、しかも電子供与性が小さく、電荷
輸送能が未だ十分でないためか、感光体を構成したとき
、帯電特性および感度が未だ十分でなく、残留電位が大
きいという問題がある。However, the above-mentioned benzidine derivatives do not have sufficient compatibility with the binder resin, have low electron donating properties, and do not yet have sufficient charge transport ability. However, there is a problem that the residual potential is large.
〈発明の目的〉
本発明は上記問題点に鑑みてなされたものであり、結着
樹脂との相溶性、帯電特性および感光特性に優れ、しか
も残留電位が小さな電子写真用感光体を提供することを
目的とする。<Object of the Invention> The present invention has been made in view of the above-mentioned problems, and it is an object of the present invention to provide an electrophotographic photoreceptor that has excellent compatibility with a binder resin, charging characteristics, and photosensitivity characteristics, and has a small residual potential. With the goal.
く問題点を解決するための手段および作用〉上記目的を
達成するため、本発明の電子写真用感光体は、導電性基
材上に感光層が形成された感光体において、上記感光層
が下記−数式(1)で表される化合物を含有することを
特徴とする。Means and Effects for Solving the Problems In order to achieve the above object, the electrophotographic photoreceptor of the present invention has a photoreceptor layer formed on a conductive base material, in which the photoreceptor layer has the following: - It is characterized by containing a compound represented by formula (1).
(式中、R’ % R2、R3、R4、R5およびR6
は、同一または異なって、水素原子、低級アルキル基、
低級アルコキシ基または)\ロゲン原子を示す。4%
m、、nおよび0は1〜5の整数を示し、pおよびqは
少なくともいずれか一方が2〜4の整数を示す。但し、
R5およびR6は同時に水素原子でないものとする。)
以下に、本発明の詳細な説明する。(In the formula, R'% R2, R3, R4, R5 and R6
are the same or different, a hydrogen atom, a lower alkyl group,
Indicates a lower alkoxy group or )\rogen atom. 4%
m, , n and 0 represent integers of 1 to 5, and at least one of p and q represents an integer of 2 to 4. however,
It is assumed that R5 and R6 are not hydrogen atoms at the same time. ) The present invention will be explained in detail below.
本発明の電子写真用感光体は、導電性基材上に上記一般
式(1)で表される化合物を含有する感光層が形成され
ている。In the electrophotographic photoreceptor of the present invention, a photosensitive layer containing a compound represented by the above general formula (1) is formed on a conductive base material.
上記導電性基材は、シート状やドラム状のいずれであっ
てもよく、基材自体が導電性を有するか、基材の表面が
導電性を有し、使用に際し十分な機械的強度を有するも
のが好ましい。上記導電性基材としては、導電性を有す
る種々の材料が使用でき、例えば、アルミニウム、銅、
錫、白金、金、銀、バナジウム、モリブデン、クロム、
カドミウム、チタン、ニッケル、パラジウム、インジウ
ム、ステンレス鋼、真鍮などの金属単体や、上記金属が
蒸着または積層されたプラスチック材料、ヨウ化アルミ
ニウム、酸化錫、酸化インジウム等で被覆されたガラス
等が例示される。上記導電性基材のうち、アルミニウム
、特に、アルミニウムの結晶粒が表面に存在せず、複写
画像等において黒点やピンホール等が発生するのを防止
すると共に、ベンジジン誘導体等を含有する感光層と基
材との密着性をよくするため、アルマイト処理されたア
ルミニウム、中でもアルマイト処理層の膜厚が5〜12
μ麿であり、表面粗さが1.5S以下のアルマイト処理
されたアルミニウムが好ましい。The above-mentioned conductive base material may be in the form of a sheet or a drum, and either the base material itself has conductivity or the surface of the base material has conductivity and has sufficient mechanical strength when used. Preferably. As the conductive base material, various conductive materials can be used, such as aluminum, copper,
tin, platinum, gold, silver, vanadium, molybdenum, chromium,
Examples include simple metals such as cadmium, titanium, nickel, palladium, indium, stainless steel, and brass, plastic materials on which the above metals are vapor-deposited or laminated, and glass coated with aluminum iodide, tin oxide, indium oxide, etc. Ru. Among the conductive substrates mentioned above, aluminum, especially aluminum crystal grains, are not present on the surface, preventing the occurrence of black spots, pinholes, etc. in copied images, etc., and a photosensitive layer containing a benzidine derivative, etc. In order to improve adhesion to the base material, alumite-treated aluminum is used, especially the thickness of the alumite-treated layer is 5 to 12 mm.
Anodized aluminum having a surface roughness of 1.5S or less is preferable.
上記感光層に含有される一般式(1)で表される化合物
において、低級アルキル基としては、メチル、エチル、
プロピル、イソプロピル、ブチル、イソブチル、ter
t−ブチル、ペンチル、ヘキシル基などの炭素数1〜6
のアルキル基が例示される。上記低級アルキル基のうち
、炭素数1〜4のアルキル基が好ましい。In the compound represented by general formula (1) contained in the photosensitive layer, the lower alkyl group includes methyl, ethyl,
propyl, isopropyl, butyl, isobutyl, ter
1-6 carbon atoms such as t-butyl, pentyl, hexyl group, etc.
An example is an alkyl group. Among the lower alkyl groups mentioned above, alkyl groups having 1 to 4 carbon atoms are preferred.
また、低級アルコキシ基としては、メトキシ、エトキシ
、プロポキシ、イソプロポキシ、ブトキシ、インブトキ
シ、tert−ブトキシ、ペンチルオキシ、ヘキシルオ
キシ基などの炭素数1〜6のアルコキシ基が例示される
。上記低級アルコキシ基のうち、炭素数1〜4のアルコ
キシ基が好ましい。Examples of lower alkoxy groups include alkoxy groups having 1 to 6 carbon atoms such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, imbutoxy, tert-butoxy, pentyloxy, and hexyloxy groups. Among the lower alkoxy groups mentioned above, alkoxy groups having 1 to 4 carbon atoms are preferred.
また、ハロゲン原子としては、フッ素、塩素、臭素およ
びヨウ素原子が挙げられる。Furthermore, examples of the halogen atom include fluorine, chlorine, bromine, and iodine atoms.
なお、置換基R’ 、R” 、R’ 、R’ 、R’お
よびR6は、ベンゼン環またはビフェニル骨格の適宜の
位置に置換していてもよい。pおよびqは少なくともい
ずれか一方が2〜4であればよく、pおよび/またはq
が2であるとき、R5および/またはR6はビフェニル
骨格の2,5−位または2’ 、5’ −位に置換して
いる化合物が好ましい。また、pおよび/またはqが3
であるとき、R5および/またはR6はビフェニル骨格
の2゜3.6−位または2’ 、3’ 、6’ −位に
置換している化合物が好ましい。特に、pおよびqの双
方が2であり、R5およびR6の双方がビフェニル骨格
の2,5−位および2’、5’ −位に置換しているベ
ンジジン誘導体が好ましい。The substituents R', R", R', R', R' and R6 may be substituted at appropriate positions on the benzene ring or biphenyl skeleton. At least one of p and q is 2-2. 4, p and/or q
When is 2, compounds in which R5 and/or R6 are substituted at the 2,5-position or the 2', 5'-position of the biphenyl skeleton are preferred. Also, p and/or q is 3
When R5 and/or R6 are substituted at the 2°3.6-position or the 2', 3', or 6'-position of the biphenyl skeleton, compounds are preferred. Particularly preferred are benzidine derivatives in which both p and q are 2, and both R5 and R6 are substituted at the 2,5-position and the 2',5'-position of the biphenyl skeleton.
上記一般式(1)で表されるベンジジン誘導体のうち、
好ましい化合物としては、例えば、下表に示上記ベンジ
ジン誘導体は一種または二種以上混合して用いられる。Among the benzidine derivatives represented by the above general formula (1),
Preferred compounds include, for example, the benzidine derivatives shown in the table below, which may be used singly or in combination of two or more.
なお、上記ベンジジン誘導体は、分子の対称性がよく、
光照射により異性化反応などが生じず、光安定性に優れ
ているだけでなく、結着樹脂との相溶性に優れ、ドリフ
ト移動度が大きく、しかもドリフト移動度に関する電界
強度依存性が小さい。従って、上記ベンジジン誘導体を
含有する感光層を備えた電子写真用感光体は、帯電性が
よく、高感度で残留電位が小さく、カブリのない高品質
の画像が得られる。In addition, the above benzidine derivative has good molecular symmetry,
It does not cause any isomerization reactions when irradiated with light, has excellent photostability, has excellent compatibility with the binder resin, has high drift mobility, and has low dependence of drift mobility on electric field strength. Therefore, an electrophotographic photoreceptor equipped with a photosensitive layer containing the above-mentioned benzidine derivative has good charging properties, high sensitivity, low residual potential, and can produce high-quality images without fog.
なお、上記一般式(1)で表される化合物は、種々の方
法、例えば、下記一般式0で表される化合物と、一般式
(3)〜(6)で表される化合物とを同時または順次反
応させることにより製造することができる。The compound represented by the general formula (1) above can be obtained by various methods, for example, by simultaneously or simultaneously treating the compound represented by the following general formula 0 and the compounds represented by general formulas (3) to (6). It can be produced by sequential reactions.
(式中、R1、R2、R3、R4、R5、R6、fl
−m % n % Olpおよびqは前記に同じ。Xは
ヨウ素などのハロゲン原子を示す。)
上記一般式(2)で表される化合物と一般式(3)〜(
6)で表される化合物との反応は、通常有機溶媒中で行
われ、溶媒としてはこの反応に悪影響を及ぼさない溶媒
であればいずれの溶媒も使用でき、例えば、ニトロベン
ゼン、ジクロロベンゼン、キノリン、N、N−ジメチル
ホルムアミド、N−メチルピロリドン、ジメチルスルホ
キシドなどの有機溶媒が例示される。該反応は、通常、
銅粉、酸化銅ハロゲン化銅などの触媒、水酸化ナトリウ
ム、水酸化カリウム、炭酸ナトリウム、炭酸カリウム、
炭酸水素ナトリウム、炭酸水素カリウムなどの塩基性物
質の存在下、150〜250℃の温度で行なわれる。(In the formula, R1, R2, R3, R4, R5, R6, fl
-m % n % Olp and q are the same as above. X represents a halogen atom such as iodine. ) A compound represented by the above general formula (2) and general formulas (3) to (
The reaction with the compound represented by 6) is usually carried out in an organic solvent, and any solvent can be used as long as it does not adversely affect this reaction, such as nitrobenzene, dichlorobenzene, quinoline, Examples include organic solvents such as N,N-dimethylformamide, N-methylpyrrolidone, and dimethylsulfoxide. The reaction is usually
Copper powder, catalysts such as copper oxide copper halide, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate,
It is carried out at a temperature of 150 to 250°C in the presence of a basic substance such as sodium hydrogen carbonate or potassium hydrogen carbonate.
また、一般式(1)で表される化合物において、置換基
R’ 、R2、R3およびR4の置換位置などが制御さ
れている化合物は、例えば、下記一般式(7)で表され
る化合物と一般式(3) (5)で表される化合物との
反応により一般式(8)で表される化合物を得た後、次
いで、一般式(8)で表される化合物を加水分解して脱
アシル化し、一般式(9)で表される化合物を得た後、
さらに一般式(4) (6)で表される化合物と反応さ
せることにより製造することができる。Furthermore, in the compound represented by the general formula (1), a compound in which the substitution positions of the substituents R', R2, R3, and R4 are controlled is, for example, a compound represented by the following general formula (7). After obtaining the compound represented by general formula (8) by the reaction with the compound represented by general formula (3) (5), the compound represented by general formula (8) is then hydrolyzed to remove After acylation to obtain a compound represented by general formula (9),
Furthermore, it can be produced by reacting with a compound represented by general formula (4) (6).
(7) Gl (5)(式中、R
7およびR6は低級アルキル基を示し、R’ 、R”
、R3、R’ 、R5、R6、J、m。(7) Gl (5) (wherein, R
7 and R6 represent lower alkyl groups, R', R''
, R3, R', R5, R6, J, m.
n s O% pSQおよびXは前記に同じ。)上記一
般式σ)で表される化合物と一般式(3) (5)で表
される化合物との反応は、前記一般式(2)で表される
化合物と一般式(3)〜(6)で表される化合物との反
応と同様にして行なうことができる。一般式(8)で表
される化合物の脱アシル化反応は、塩基性触媒の存在下
、常法により行なうことができる。また、上記一般式〇
)で表される化合物と一般式(4) (6)で表される
化合物との反応は、前記一般式■で表される化合物と一
般式(3)〜(6)で表される化合物との反応と同様に
行なうことができる。n s O% pSQ and X are the same as above. ) The reaction between the compound represented by the above general formula σ) and the compound represented by the general formulas (3) (5) is the reaction between the compound represented by the above general formula (2) and the general formulas (3) to (6). ) can be carried out in the same manner as the reaction with the compound represented by. The deacylation reaction of the compound represented by the general formula (8) can be carried out by a conventional method in the presence of a basic catalyst. Furthermore, the reaction between the compound represented by the above general formula ○) and the compound represented by the general formulas (4) and (6) is the reaction between the compound represented by the above general formula (■) and the general formulas (3) to (6). It can be carried out in the same manner as the reaction with the compound represented by.
なお、前記一般式(1)で表される化合物において、置
換基R1、R2、R3、R4、R5およびR6がハロゲ
ン原子である化合物は、上記反応の後、反応生成物をハ
ロゲン化することにより製造してもよい。In addition, in the compound represented by the general formula (1), the compound in which the substituents R1, R2, R3, R4, R5 and R6 are halogen atoms can be prepared by halogenating the reaction product after the above reaction. May be manufactured.
反応終了後、反応混合物を濃縮し、精製することなく、
または再結晶、溶媒抽出、カラムクロマトグラフィー等
の慣用の手段で容易に分離精製することができる。After the reaction is complete, the reaction mixture is concentrated and purified without purification.
Alternatively, it can be easily separated and purified by conventional means such as recrystallization, solvent extraction, and column chromatography.
なお、前記のように一般式(1)で表される化合物は、
電荷の輸送性に優れ、高感度で残留電位が小さな感光体
が得られるが、必要に応じて、帯電特性、感光特性など
を阻害しない範囲で、他の電荷輸送材料と併用してもよ
い。上記他の電荷輸送材料としては、例えば、テトラシ
アノエチレン、2゜4.7−ドリニトロー9−フルオレ
ノン等のフルオレノン系化合物、2,4.8−)−リニ
トロチオキサントン、ジニトロアントラセン等のニトロ
化化合物、無水コハク酸、無水マレイン酸、ジブロモ無
水マレイン酸、2.5−ジ(4−ジメチルアミノフェニ
ル)−1,3,4−オキサジ°アゾール等のオキサジア
ゾール系化合物、9−(4−ジエチルアミノスチリル)
アントラセン等のスチリル系化合物、ポリビニルカルバ
ゾール等のカルバゾール系化合物、1−フェニル−3−
(p−ジメチルアミノフェニル)ピラゾリン等のピラゾ
リン系化合物、4.4’ 、4’−トリス(4−ジエチ
ルアミノフェニル)トリフェニルアミンなどのアミン誘
導体、1,1−ジフェニル−4,4−ビス(4−ジメチ
ルアミノフェニル)−1,3−ブタジェンなどの共役系
化合物、4− (N、N−ジエチルアミノ)ベンズアル
デヒド N、N−ジフェニルヒドラゾンなどのヒドラゾ
ン系化合物、インドール系化合物、オキサゾール系化合
物、イソオキサゾール系化合物、チアゾール系化合物、
チアジアゾール系化合物、イミダゾール系化合物、ピラ
ゾール系化合物、トリアゾール系化合物等の含窒素環式
化合物、縮合多環族化合物等が例示される。なお、前記
電荷輸送材料としての光導電性ポリマー、例えば、ポリ
−N−ビニルカルバゾール等は結着樹脂として使用して
もよい。In addition, as mentioned above, the compound represented by the general formula (1) is
A photoreceptor with excellent charge transport properties, high sensitivity, and low residual potential can be obtained, but if necessary, it may be used in combination with other charge transport materials as long as the charging characteristics, photosensitivity characteristics, etc. are not impaired. Examples of the other charge transport materials include tetracyanoethylene, fluorenone compounds such as 2°4.7-dolinitro-9-fluorenone, and nitrated compounds such as 2,4.8-)-linitrothioxanthone and dinitroanthracene. , succinic anhydride, maleic anhydride, dibromomaleic anhydride, oxadiazole compounds such as 2,5-di(4-dimethylaminophenyl)-1,3,4-oxadiazole, 9-(4-diethylamino Styril)
Styryl compounds such as anthracene, carbazole compounds such as polyvinylcarbazole, 1-phenyl-3-
Pyrazoline compounds such as (p-dimethylaminophenyl)pyrazoline, amine derivatives such as 4,4',4'-tris(4-diethylaminophenyl)triphenylamine, 1,1-diphenyl-4,4-bis(4 Conjugated compounds such as -dimethylaminophenyl)-1,3-butadiene, hydrazone compounds such as 4-(N,N-diethylamino)benzaldehyde N,N-diphenylhydrazone, indole compounds, oxazole compounds, isoxazole compounds compounds, thiazole compounds,
Examples include nitrogen-containing cyclic compounds such as thiadiazole compounds, imidazole compounds, pyrazole compounds, and triazole compounds, and fused polycyclic compounds. Note that the photoconductive polymer as the charge transporting material, such as poly-N-vinylcarbazole, may be used as a binder resin.
前記一般式(1)で表される化合物を含有する感光層と
しては、電荷発生材料と上記一般式(1)の化合物と結
着樹脂とを含有する単層型感光層や、少なくとも電荷発
生材料を含有する電荷発生層と、上記一般式(1)で表
される化合物と結着樹脂とを含有する電荷輸送層とが積
層された積層型感光層のいずれであってもよい。また、
上記積層型感光層は、電荷発生層上に電荷輸送層が形成
されていたり、これとは逆に電荷輸送層上に電荷発生層
が形成されていてもよい。The photosensitive layer containing the compound represented by the general formula (1) above may be a single-layer photosensitive layer containing a charge generating material, the compound represented by the above general formula (1), and a binder resin, or at least a charge generating material. The photosensitive layer may be any of a laminated type photosensitive layer in which a charge generation layer containing the above compound and a charge transport layer containing the compound represented by the above general formula (1) and a binder resin are laminated. Also,
In the laminated photosensitive layer, the charge transport layer may be formed on the charge generation layer, or conversely, the charge generation layer may be formed on the charge transport layer.
上記電荷発生材料としては、例えば、セレン、セレン−
テルル、アモルファスシリコン、ピリリウム塩、アゾ系
化合物、ジスアゾ系化合物、フタロシアニン系化合物、
アンサンスロン系化合物、ペリレン系化合物、インジゴ
系化合物、トリフェニルメタン系化合物、スレン系化合
物、トルイジン系化合物、ピラゾリン系化合物、キナク
リドン系化合物等が例示される。上記電荷発生材料は、
一種または二種以上使用される。Examples of the charge generating material include selenium, selenium-
Tellurium, amorphous silicon, pyrylium salts, azo compounds, disazo compounds, phthalocyanine compounds,
Examples include anthanthrone compounds, perylene compounds, indigo compounds, triphenylmethane compounds, threne compounds, toluidine compounds, pyrazoline compounds, and quinacridone compounds. The above charge generating material is
One or more types are used.
なお、上記電荷発生材料は、適宜選択することができる
が、分光感度を高めるため、フタロシアニン系化合物、
例えば、α型、β型、γ型など、種々の結晶型を有する
アルミニウムフタロシアニン、銅フタロシアニン、バナ
ジルフタロシアニン、中でもメタルフリーフタロシアニ
ンおよび/またはチタニルフタロシアニンを少なくとも
含有するものが好ましい。上記フタロシアニン系化合物
は、適宜の粒径を有していてもよいが、平均粒径0゜1
μm以下のものが好ましい。メタルフリーフタロシアニ
ンの平均粒径が0.1μmを越えると感光体の感度が低
下する。The charge generating material described above can be selected as appropriate, but in order to increase the spectral sensitivity, phthalocyanine compounds,
For example, among aluminum phthalocyanine, copper phthalocyanine, and vanadyl phthalocyanine having various crystal forms such as α type, β type, and γ type, those containing at least metal-free phthalocyanine and/or titanyl phthalocyanine are preferred. The above phthalocyanine compound may have an appropriate particle size, but the average particle size is 0°1.
Preferably, the thickness is less than μm. When the average particle size of the metal-free phthalocyanine exceeds 0.1 μm, the sensitivity of the photoreceptor decreases.
また、上記結着樹脂としては、種々のもの、例えば、ス
チレン系重合体、アクリル系重合体、スチレン−アクリ
ル系共重合体、ポリエチレン、エチレン−酢酸ビニル共
重合体、塩素化ポリエチレン、ポリプロピレン、アイオ
ノマー等のオレフィン系重合体、ポリ塩化ビニル、塩化
ビニル−酢酸ビニル共重合体、ポリエステル、アルキッ
ド樹脂、ポリアミド、ポリウレタン、エポキシ樹脂、ポ
リカーボネート、ボリアリレート、ポリスルホン、ジア
リルフタレート樹脂、シリコーン樹脂、ケトン樹脂、ポ
リビニルブチラール樹脂、ポリエーテル樹脂、フェノー
ル樹脂や、エポキシアクリレート等の光硬化型樹脂等、
各種の重合体が例示される。上記結着樹脂は一種または
二種以上用いられる。In addition, various binder resins can be used, such as styrene polymers, acrylic polymers, styrene-acrylic copolymers, polyethylene, ethylene-vinyl acetate copolymers, chlorinated polyethylene, polypropylene, and ionomers. Olefin polymers such as polyvinyl chloride, vinyl chloride-vinyl acetate copolymer, polyester, alkyd resin, polyamide, polyurethane, epoxy resin, polycarbonate, polyarylate, polysulfone, diallyl phthalate resin, silicone resin, ketone resin, polyvinyl Butyral resin, polyether resin, phenol resin, photocurable resin such as epoxy acrylate, etc.
Various polymers are exemplified. One or more types of the above-mentioned binder resins may be used.
また、感光層は、ターフェニル、ハロナフトキノン類、
アセナフチレン等、従来公知の増感剤、9− (N、N
−ジフェニルヒドラジノ)フルオレン、9−カルバゾリ
ルイミノフルオレンなどのフルオレン系化合物、可塑剤
、酸化防止剤、紫外線吸収剤などの劣化防止剤等、種々
の添加剤を含有していてもよい。In addition, the photosensitive layer includes terphenyl, halonaphthoquinones,
Conventionally known sensitizers such as acenaphthylene, 9-(N,N
It may contain various additives such as fluorene compounds such as -diphenylhydrazino)fluorene and 9-carbazolyliminofluorene, deterioration inhibitors such as plasticizers, antioxidants, and ultraviolet absorbers.
前記単層型感光層における電荷発生材料と一般式(1)
で表される化合物と結着樹脂との使用割合は、特に限定
されず、所望する電子写真用感光体の特性等に応じて適
宜選択することができるが、結着樹脂100重量部に対
して電荷発生材料2〜20重量部、特に3〜15重量部
、一般式(1)で表される化合物40〜200重量部、
特に50〜100重量部からなるものが好ましい。電荷
発生材料および一般式(1)で表される化合物が上記量
よりも少ないと、感光体の感度が十分でないばかりか、
残留電位が大きくなる。また上記範囲を越えると感光体
の耐摩耗性等が十分でなくなる。Charge generating material in the single-layer photosensitive layer and general formula (1)
The ratio of the compound represented by the formula to the binder resin is not particularly limited and can be appropriately selected depending on the desired characteristics of the electrophotographic photoreceptor, but the ratio is based on 100 parts by weight of the binder resin. 2 to 20 parts by weight of charge generating material, especially 3 to 15 parts by weight, 40 to 200 parts by weight of a compound represented by general formula (1),
Particularly preferred is one containing 50 to 100 parts by weight. If the amount of the charge generating material and the compound represented by general formula (1) is less than the above amount, not only will the sensitivity of the photoreceptor be insufficient,
Residual potential increases. Further, if the amount exceeds the above range, the abrasion resistance of the photoreceptor will not be sufficient.
単層型感光層は、適宜の厚みを有していてもよいが、1
0〜50μ層、特に15〜25μmの厚みを有するもの
が好ましい。The single-layer type photosensitive layer may have an appropriate thickness, but 1
Preference is given to those having a thickness of 0 to 50 μm, especially 15 to 25 μm.
また、積層型感光層における電荷発生層は、前記電荷発
生材料からなる蒸着膜、スパッタリング膜などで形成さ
れていてもよく、電荷発生層が結着樹脂とともに形成さ
れている場合、電荷発生層における電荷発生材料と結着
樹脂との割合は適宜設定することができるが、結着樹脂
100重量部に対して電荷発生材料5〜5000重量部
、特に10〜2500重量部からなるものが好ましい。Further, the charge generation layer in the laminated photosensitive layer may be formed of a vapor deposited film, a sputtered film, etc. made of the charge generation material, and when the charge generation layer is formed together with a binder resin, the charge generation layer The ratio of the charge generating material to the binder resin can be set as appropriate, but it is preferably 5 to 5,000 parts by weight, particularly 10 to 2,500 parts by weight of the charge generating material per 100 parts by weight of the binder resin.
電荷発生材料が5重量部未満であると電荷発生能が小さ
く、5000重量部を越えると密着性が低下する等の問
題がある。上記電荷発生層は、適宜の厚みを有していて
もよいが、0.01〜30μ鳳、特に0.1〜20μm
程度の厚みを有するものが好ましい。If the amount of the charge generating material is less than 5 parts by weight, the charge generating ability will be low, and if it exceeds 5,000 parts by weight, there will be problems such as poor adhesion. The charge generation layer may have an appropriate thickness, but may have a thickness of 0.01 to 30 μm, particularly 0.1 to 20 μm.
It is preferable to have a certain thickness.
また、電荷輸送層における一般式(1)で表される化合
物と結着樹脂との割合は適宜設定することができるが、
結着樹脂100重量部に対して、一般式(1)で表され
る化合物10〜500重量部、特に25〜200重量部
からなるものが好ましい。−般式(1)で表される化合
物が、10重量部未満であると電荷輸送能が十分でなく
、500重量部を越えると電荷輸送層の機械的強度等が
低下する。上記電荷輸送層は、適宜の厚みを有していて
もよいが、2〜100μ厘、特に5〜30μm程度の厚
みを有するものが好ましい。Furthermore, the ratio of the compound represented by general formula (1) and the binder resin in the charge transport layer can be set as appropriate;
Preferably, the amount of the compound represented by formula (1) is 10 to 500 parts by weight, particularly 25 to 200 parts by weight, per 100 parts by weight of the binder resin. - If the amount of the compound represented by general formula (1) is less than 10 parts by weight, the charge transport ability will not be sufficient, and if it exceeds 500 parts by weight, the mechanical strength etc. of the charge transport layer will decrease. The charge transport layer may have an appropriate thickness, but preferably has a thickness of about 2 to 100 μm, particularly about 5 to 30 μm.
また、前記電荷発生層は、電荷発生材料とともに電荷輸
送材料を含有していてもよく、この場合、電荷発生層に
おける電荷発生材料と電荷輸送材料と結着樹脂との割合
は適宜設定されるが、前記単層型感光層における電荷発
生材料と電荷輸送材料と結着樹脂と同様の割合で構成さ
れたものが好ましい。また、上記のような割合からなる
電荷発生層は、適宜の厚みに形成されるが、通常、0.
1〜50μm程度に形成される。Further, the charge generation layer may contain a charge transport material together with the charge generation material, and in this case, the ratio of the charge generation material, the charge transport material, and the binder resin in the charge generation layer is set as appropriate. It is preferable that the charge generating material, the charge transporting material, and the binder resin are comprised in the same proportions as in the single-layer type photosensitive layer. Further, the charge generation layer having the above-mentioned ratio is formed to have an appropriate thickness, but is usually 0.000.
It is formed to have a thickness of about 1 to 50 μm.
上記単層型感光層は、電荷発生材料と一般式〔1)で表
される化合物と結着樹脂などを含有する感光層用分散液
を調製し、該分散液を前記導電性基材に塗布し、乾燥ま
たは硬化させることにより形成することができる。また
、積層型感光層は、電荷発生材料と結着樹脂などを含有
する電荷発生層用分散液と、前記一般式(1)で表され
る化合物と結着樹脂などを含有する電荷輸送層用塗布液
をそれぞれ調製し、導電性基材に順次塗布し、乾燥また
は硬化させることにより形成することができる。The single-layer type photosensitive layer is prepared by preparing a photosensitive layer dispersion containing a charge generating material, a compound represented by the general formula [1), a binder resin, etc., and coating the dispersion on the conductive base material. It can be formed by drying or curing. The laminated photosensitive layer includes a charge generation layer dispersion containing a charge generation material and a binder resin, and a charge transport layer dispersion containing a compound represented by the general formula (1) and a binder resin. It can be formed by preparing respective coating liquids, sequentially applying them to a conductive substrate, and drying or curing them.
また、上記分散液などの調製に際しては、使用される結
着樹脂等の種類に応じて種々の有機溶剤を使用すること
ができる。上記溶剤としては、n−へキサン、オクタン
、シクロヘキサン等の脂肪族系炭化水素、ベンゼン、ト
ルエン、キシレン等の芳香族炭化水素、ジクロロメタン
、ジクロロエタン、四塩化炭素、クロロベンゼン等のハ
ロゲン化炭化水素、ジメチルエーテル、ジエチルエーテ
ル、テトラヒドロフラン、エチレングリコールジメチル
エーテル、エチレングリコールジエチルエーテル、ジエ
チレングリコールジメチルエーテル等のエーテル類、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、酢酸メチル等のエステル類、ジメ
チルホルムアミド、ジメチルスルホキシド等、種々の溶
剤が例示され、一種または二種以上混合して用いられる
。なお、上記分散液などを調製する際、分散性、塗工性
等をよくするため、界面活性剤、レベリング剤等を併用
してもよい。Further, when preparing the above-mentioned dispersion liquid, etc., various organic solvents can be used depending on the type of binder resin etc. used. The above-mentioned solvents include aliphatic hydrocarbons such as n-hexane, octane, and cyclohexane, aromatic hydrocarbons such as benzene, toluene, and xylene, halogenated hydrocarbons such as dichloromethane, dichloroethane, carbon tetrachloride, and chlorobenzene, and dimethyl ether. , ethers such as diethyl ether, tetrahydrofuran, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, diethylene glycol dimethyl ether, ketones such as acetone, methyl ethyl ketone, cyclohexanone, esters such as ethyl acetate, methyl acetate, dimethyl formamide, dimethyl sulfoxide, etc. The following solvents are exemplified and may be used alone or in combination of two or more. In addition, when preparing the above-mentioned dispersion liquid, etc., a surfactant, a leveling agent, etc. may be used in combination in order to improve dispersibility, coating properties, etc.
また、上記分散液などは、従来慣用の方法、例えば、ミ
キサ、ボールミル、ペイントシェーカー、サンドミル、
アトライター、超音波分散器等を用いて調製することが
でき、得られた分散液などを前記導電性基材に塗布し、
加熱して溶剤を除去することにより、本発明の電子写真
用感光体を得ることができる。In addition, the above-mentioned dispersion liquid can be prepared using conventional methods such as mixer, ball mill, paint shaker, sand mill, etc.
It can be prepared using an attritor, an ultrasonic disperser, etc., and the obtained dispersion etc. is applied to the conductive substrate,
The electrophotographic photoreceptor of the present invention can be obtained by heating to remove the solvent.
なお、前記導電性基材と感光層との密着性を高めるため
、導電性基材と感光層との間に下引き層を形成してもよ
い。該下引き層は、天然または合成高分子を含有する溶
液を塗布し、乾燥後の膜厚が0.01〜1μm程度にな
るように形成される。Incidentally, in order to improve the adhesion between the conductive base material and the photosensitive layer, an undercoat layer may be formed between the conductive base material and the photosensitive layer. The undercoat layer is formed by applying a solution containing a natural or synthetic polymer so that the film thickness after drying is approximately 0.01 to 1 μm.
また、導電性基材と感光層との密着性を高めるため、導
電性基材は、シランカップリング剤、チタンカップリン
グ剤などの表面処理剤で処理されていてもよい。さらに
は、前記感光層を保護するため、感光層上に表面保護層
を形成してもよい。前記表面保護層は、前記種々の結着
樹脂や、該結着樹脂と劣化防止剤等の添加剤との混合液
を通常、乾燥後の膜厚0.1〜10μm1好ましくは0
. 2〜5−程度に塗布することにより形成される。Further, in order to improve the adhesion between the conductive base material and the photosensitive layer, the conductive base material may be treated with a surface treatment agent such as a silane coupling agent or a titanium coupling agent. Furthermore, in order to protect the photosensitive layer, a surface protective layer may be formed on the photosensitive layer. The surface protective layer is usually made of the various binder resins or a mixed solution of the binder resin and additives such as anti-deterioration agents to a film thickness of 0.1 to 10 μm after drying, preferably 0.
.. It is formed by applying about 2 to 5 coats.
本発明の電子写真用感光体は、感光層が、前記一般式(
1)で表される化合物を含有しているため、光安定性に
優れると共に、感度および表面電位が高く、しかも残留
電位が小さい。従って、本発明の電子写真用感光体は、
複写機、レーザビームプリンターなどで使用される感光
体として有用である。In the electrophotographic photoreceptor of the present invention, the photosensitive layer has the general formula (
Since it contains the compound represented by 1), it has excellent photostability, high sensitivity and surface potential, and low residual potential. Therefore, the electrophotographic photoreceptor of the present invention is
It is useful as a photoreceptor used in copying machines, laser beam printers, etc.
〈実施例〉
以下に、実施例に基づき、本発明をより詳細に説明する
。<Examples> The present invention will be described in more detail below based on Examples.
電荷発生材料としてのN、N’ −ジメチルペリレン−
3,4,9,10−テトラカルボキシシイ、′。N,N'-dimethylperylene- as a charge generating material
3,4,9,10-tetracarboxy,'.
ドと、前記表中に示された化合物とを用い、積層型感光
層を有する電子写真用感光体と、単層型電子写真用感光
体とを以下のようにして作製した。An electrophotographic photoreceptor having a laminated photosensitive layer and a single-layer electrophotographic photoreceptor were prepared using the compound shown in the above table as follows.
実施例1〜7
積層型感光層を有する電子写真用感光体上記電荷発生材
料10重量部、塩化ビニル−酢酸ビニル共重合体(漬水
化学工業社製、商品名工スレツクC)10重量部および
所定量のテトラヒドロフランからなる電荷発生層用塗布
液を調製し、得られた塗布液をアルミニウムシート上に
塗布し、100℃の温度で30分間加熱することにより
、膜厚的0.5μ■の電荷発生層を形成した。Examples 1 to 7 Photoreceptor for electrophotography having a laminated photosensitive layer 10 parts by weight of the above charge generating material, 10 parts by weight of vinyl chloride-vinyl acetate copolymer (manufactured by Tsukisui Kagaku Kogyo Co., Ltd., trade name: Meiko Sletsku C) and A charge generation layer coating solution consisting of a fixed amount of tetrahydrofuran is prepared, and the resulting coating solution is applied onto an aluminum sheet and heated at 100°C for 30 minutes to generate a charge with a film thickness of 0.5μ. formed a layer.
次いで、前記表に示された化合物No、を電荷輸送材料
として用い、電荷輸送層を形成した。すなわち、表1に
示される化合物7重量部、ビスフェノールZ型車リカー
ボネート(三菱瓦斯化学社製、商品名PCZ)10重量
部および所定量のベンゼンを混合溶解し、電荷輸送層用
塗布液を調製するとともに、前記電荷発生層上に塗布し
、加熱乾燥することにより、膜厚的25μmの電荷輸送
層を形成し、積層型感光層を有する電子写真用感光体を
作製した。Next, a charge transport layer was formed using compound No. shown in the table above as a charge transport material. That is, 7 parts by weight of the compound shown in Table 1, 10 parts by weight of bisphenol Z type car recarbonate (manufactured by Mitsubishi Gas Chemical Co., Ltd., trade name PCZ), and a predetermined amount of benzene were mixed and dissolved to prepare a coating liquid for the charge transport layer. At the same time, a charge transport layer having a film thickness of 25 μm was formed by coating on the charge generation layer and heating and drying, thereby producing an electrophotographic photoreceptor having a laminated photosensitive layer.
比較例1〜3
実施例1〜7の電荷輸送材料に代えて、4゜4′−ビス
[N−フェニル−N−(3−メチルフェニル)アミノコ
ジフェニル(比較例1) 、4゜4′−ビス[N、N−
ジ(4−メチルフェニル)アミノ]−2,2’−ジメチ
ルジフェニル(比較例2) 、4.4’ −ビス[N
、N−ジ(4−メチルフェニル)アミノ]−3,3’
−ジメチルジフェニル(比較例3)を用い、上記実施例
1〜7と同様にして、積層型感光層を有する電子写真用
感光体を作製した。Comparative Examples 1 to 3 In place of the charge transport materials of Examples 1 to 7, 4°4'-bis[N-phenyl-N-(3-methylphenyl)aminocodiphenyl (Comparative Example 1), 4°4' -Bis [N, N-
di(4-methylphenyl)amino]-2,2'-dimethyldiphenyl (Comparative Example 2), 4,4'-bis[N
, N-di(4-methylphenyl)amino]-3,3'
- Using dimethyldiphenyl (Comparative Example 3), an electrophotographic photoreceptor having a laminated photosensitive layer was produced in the same manner as in Examples 1 to 7 above.
実施例8〜14
単層型感光層を有する電子写真用感光体上記電荷発生材
料8重量部、表2に示す化合物70重量部、ビスフェノ
ールA型ポリカーボネート(金入化成社製、商品名パン
ライトL−12253100重量部および所定量のテト
ラヒドロフランからなる単層型感光層用塗布液を調製し
、アルミニウムシート上に塗布し、100℃の温度で3
0分間加熱することにより、膜厚的25μmの単層型感
光層を有する電子写真用感光体を作製した。Examples 8 to 14 Photoreceptor for electrophotography having a single-layer type photosensitive layer 8 parts by weight of the above charge generating material, 70 parts by weight of the compound shown in Table 2, bisphenol A type polycarbonate (manufactured by Kaneni Kasei Co., Ltd., trade name: Panlite L) A coating solution for a single layer type photosensitive layer consisting of 100 parts by weight of -12253 and a predetermined amount of tetrahydrofuran was prepared, coated on an aluminum sheet, and heated at a temperature of 100°C for 30 minutes.
By heating for 0 minutes, an electrophotographic photoreceptor having a single-layer photosensitive layer with a thickness of 25 μm was produced.
比較例4〜6
上記実施例8〜14の電荷輸送材料に代えて、比較例1
〜3の電荷輸送材料を用い、前記実施例8〜14と同様
にして、単層型感光層を有する電子写真用感光体を作製
した。Comparative Examples 4 to 6 Comparative Example 1 was used instead of the charge transport material of Examples 8 to 14 above.
Electrophotographic photoreceptors having a single-layer type photosensitive layer were prepared in the same manner as in Examples 8 to 14 using the charge transport materials No. 3 to 3.
そして、上記実施例および比較例で得られた電子写真用
感光体の帯電特性、感光特性を調べるため、静電複写紙
試験装置(川口電機社製、5P−428型)を用いて、
積層型感光層を有する感光体では−6,0KV、単層型
感光層を有する感光体では+6.OKVの条件でコロナ
放電を行なうことにより、前記各実施例および比較例の
電子写真用感光体を負または正に帯電させた。また、各
感光体の初期表面電位V s、p、 (V)を測定する
と共に、10ルツクスのタングステンランプを用いて、
感光体表面を露光し、上記表面電位V s、p、が1/
2となるまでの時間を求め、半減露光量E l/2(L
ow 、・see、)を算出した。さらには、露光後、
0.15秒経過後の表面電位を残留電位V r、p。Then, in order to examine the charging characteristics and photosensitivity characteristics of the electrophotographic photoreceptors obtained in the above Examples and Comparative Examples, an electrostatic copying paper tester (manufactured by Kawaguchi Electric Co., Ltd., Model 5P-428) was used.
-6.0 KV for a photoreceptor with a laminated photosensitive layer, +6.0 KV for a photoreceptor with a single layer photosensitive layer. The electrophotographic photoreceptors of each of the Examples and Comparative Examples were negatively or positively charged by performing corona discharge under OKV conditions. In addition, the initial surface potential Vs, p, (V) of each photoreceptor was measured, and using a 10 lux tungsten lamp,
The surface of the photoreceptor is exposed to light, and the surface potential V s,p becomes 1/
Find the time until it becomes 2, and calculate the half-decreased exposure amount E l/2 (L
ow, ·see,) was calculated. Furthermore, after exposure,
The surface potential after 0.15 seconds has passed is the residual potential V r,p.
(■)とした。(■)
上記実施例および比較例で得られた各電子写真用感光体
の帯電特性、感光特性などの結果を表1および2に示す
。Tables 1 and 2 show the charging characteristics, photosensitive characteristics, etc. of each electrophotographic photoreceptor obtained in the above Examples and Comparative Examples.
(以下、余白)
表1および2に示すように、比較例の積層型または単層
型感光層を有する電子写真用感光体は、いずれも感度が
小さく、残留電位が高いことが判明した。これに対して
、実施例の電子写真用感光体は、いずれも感度が大きく
、残留電位が低いことが判明した。(Hereinafter, blank spaces) As shown in Tables 1 and 2, it was found that the electrophotographic photoreceptors of Comparative Examples having a laminated type or single layer type photosensitive layer all had low sensitivity and high residual potential. On the other hand, all of the electrophotographic photoreceptors of Examples were found to have high sensitivity and low residual potential.
〈発明の効果〉
以上のように、本発明の電子写真用感光体によれば、感
光層が、前記一般式(1)で表される化合物を含有して
いるため、感度が高く、しかも残留電位が小さいという
特有の効果を奏する。<Effects of the Invention> As described above, according to the electrophotographic photoreceptor of the present invention, since the photosensitive layer contains the compound represented by the general formula (1), the sensitivity is high and there is no residual It has the unique effect of having a low potential.
Claims (1)
、上記感光層が下記一般式(1)で表される化合物を含
有することを特徴とする電子写真用感光体。 ▲数式、化学式、表等があります▼(1) (式中、R^1、R^2、R^3、R^4、R^5およ
びR^6は、同一または異なって、水素原子、低級アル
キル基、低級アルコキシ基またはハロゲン原子を示す。 l、m、nおよびoは1〜5の整数を示し、pおよびq
は少なくともいずれか一方が2〜4の整数を示す。但し
、R^5およびR^6は同時に水素原子でないものとす
る。) 2、R^1、R^2、R^3、R^4、R^5およびR
^6が、同一または異なって、水素原子、炭素数1〜4
のアルキル基、炭素数1〜4のアルコキシ基またはハロ
ゲン原子である上記特許請求の範囲第1項記載の電子写
真用感光体。 3、pおよびqが2であり、R^5およびR^6がビフ
ェニル骨格の2、5−位および2′、5′−位に置換し
ている上記特許請求の範囲第1項記載の電子写真用感光
体。 4、pおよびqが3であり、R^5およびR^6がビフ
ェニル骨格の2、3、6−位および2′、3′、6′−
位に置換している上記特許請求の範囲第1項記載の電子
写真用感光体。 5、感光層が、メタルフリーフタロシアニンまたはチタ
ニルフタロシアニンを含有する上記特許請求の範囲第1
項記載の電子写真用感光体。[Scope of Claims] 1. A photoreceptor having a photosensitive layer formed on a conductive base material, for use in electrophotography, characterized in that the photosensitive layer contains a compound represented by the following general formula (1). Photoreceptor. ▲There are mathematical formulas, chemical formulas, tables, etc.▼(1) (In the formula, R^1, R^2, R^3, R^4, R^5 and R^6 are the same or different and are hydrogen atoms, It represents a lower alkyl group, a lower alkoxy group or a halogen atom. l, m, n and o represent integers of 1 to 5, p and q
At least one of these represents an integer of 2 to 4. However, R^5 and R^6 are not hydrogen atoms at the same time. ) 2, R^1, R^2, R^3, R^4, R^5 and R
^6 is the same or different, hydrogen atom, carbon number 1-4
The electrophotographic photoreceptor according to claim 1, which is an alkyl group, an alkoxy group having 1 to 4 carbon atoms, or a halogen atom. 3, p and q are 2, and R^5 and R^6 are substituted at the 2, 5-position and the 2', 5'-position of the biphenyl skeleton; Photographic photoreceptor. 4, p and q are 3, and R^5 and R^6 are the 2, 3, 6-positions and the 2', 3', 6'- positions of the biphenyl skeleton.
The electrophotographic photoreceptor according to claim 1, wherein the electrophotographic photoreceptor is substituted at this position. 5. Claim 1 above, wherein the photosensitive layer contains metal-free phthalocyanine or titanyl phthalocyanine.
The electrophotographic photoreceptor described in .
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP62301862A JP2573261B2 (en) | 1987-11-30 | 1987-11-30 | Electrophotographic photoreceptor |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP62301862A JP2573261B2 (en) | 1987-11-30 | 1987-11-30 | Electrophotographic photoreceptor |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH01142647A true JPH01142647A (en) | 1989-06-05 |
JP2573261B2 JP2573261B2 (en) | 1997-01-22 |
Family
ID=17902053
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP62301862A Expired - Fee Related JP2573261B2 (en) | 1987-11-30 | 1987-11-30 | Electrophotographic photoreceptor |
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Country | Link |
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH01315751A (en) * | 1988-03-08 | 1989-12-20 | Canon Inc | Electrophotographic sensitive body |
JPH04310962A (en) * | 1991-01-14 | 1992-11-02 | Xerox Corp | Organic composition and photoconductive picture forming member |
EP0648737A1 (en) * | 1993-10-13 | 1995-04-19 | Mita Industrial Co. Ltd. | Benzidine derivatives and electrophotosensitive material using the same |
-
1987
- 1987-11-30 JP JP62301862A patent/JP2573261B2/en not_active Expired - Fee Related
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH01315751A (en) * | 1988-03-08 | 1989-12-20 | Canon Inc | Electrophotographic sensitive body |
JPH059786B2 (en) * | 1988-03-08 | 1993-02-05 | Canon Kk | |
JPH04310962A (en) * | 1991-01-14 | 1992-11-02 | Xerox Corp | Organic composition and photoconductive picture forming member |
EP0648737A1 (en) * | 1993-10-13 | 1995-04-19 | Mita Industrial Co. Ltd. | Benzidine derivatives and electrophotosensitive material using the same |
Also Published As
Publication number | Publication date |
---|---|
JP2573261B2 (en) | 1997-01-22 |
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