JPH0516018B2 - - Google Patents
Info
- Publication number
- JPH0516018B2 JPH0516018B2 JP63330987A JP33098788A JPH0516018B2 JP H0516018 B2 JPH0516018 B2 JP H0516018B2 JP 63330987 A JP63330987 A JP 63330987A JP 33098788 A JP33098788 A JP 33098788A JP H0516018 B2 JPH0516018 B2 JP H0516018B2
- Authority
- JP
- Japan
- Prior art keywords
- resin
- charge
- layer
- charge transport
- electrophotographic
- 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.)
- Expired - Fee Related
Links
- 108091008695 photoreceptors Proteins 0.000 claims description 31
- -1 triarylamine compound Chemical class 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 229930195733 hydrocarbon Natural products 0.000 claims description 5
- 150000002430 hydrocarbons Chemical class 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 239000010410 layer Substances 0.000 description 52
- 150000001875 compounds Chemical class 0.000 description 19
- 239000000975 dye Substances 0.000 description 17
- 239000000049 pigment Substances 0.000 description 16
- 239000000463 material Substances 0.000 description 13
- 229920005989 resin Polymers 0.000 description 13
- 239000011347 resin Substances 0.000 description 13
- 239000011230 binding agent Substances 0.000 description 10
- 238000000576 coating method Methods 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 7
- 239000010408 film Substances 0.000 description 7
- 230000035945 sensitivity Effects 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000002800 charge carrier Substances 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 239000004677 Nylon Substances 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- 229920001778 nylon Polymers 0.000 description 4
- 229920002382 photo conductive polymer Polymers 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical group ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 3
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical compound C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 3
- 229910052711 selenium Inorganic materials 0.000 description 3
- 239000011669 selenium Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 3
- 229910001887 tin oxide Inorganic materials 0.000 description 3
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 3
- 239000011787 zinc oxide Substances 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-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
- 229920000178 Acrylic resin Polymers 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- 229910000838 Al alloy Inorganic materials 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001408 amides Chemical class 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
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 229910052980 cadmium sulfide Inorganic materials 0.000 description 2
- 239000005018 casein Substances 0.000 description 2
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 2
- 235000021240 caseins Nutrition 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- 229940117389 dichlorobenzene Drugs 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000005496 eutectics Effects 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910003437 indium oxide Inorganic materials 0.000 description 2
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 229920006287 phenoxy resin Polymers 0.000 description 2
- 239000013034 phenoxy resin Substances 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
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 229920002285 poly(styrene-co-acrylonitrile) Polymers 0.000 description 2
- 229920001230 polyarylate Polymers 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920005668 polycarbonate resin Polymers 0.000 description 2
- 239000004431 polycarbonate resin Substances 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 229920002451 polyvinyl alcohol 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
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229920003048 styrene butadiene rubber Polymers 0.000 description 2
- 150000003462 sulfoxides Chemical class 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 238000007738 vacuum evaporation Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-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
- NXYICUMSYKIABQ-UHFFFAOYSA-N 1-iodo-4-phenylbenzene Chemical group C1=CC(I)=CC=C1C1=CC=CC=C1 NXYICUMSYKIABQ-UHFFFAOYSA-N 0.000 description 1
- HIPJINRMIDCBDO-UHFFFAOYSA-N 2,6,6-trimethylcyclohexa-1,3-diene Chemical compound CC1=CC(C)(C)CC=C1 HIPJINRMIDCBDO-UHFFFAOYSA-N 0.000 description 1
- HCSGQHDONHRJCM-CCEZHUSRSA-N 9-[(e)-2-phenylethenyl]anthracene Chemical class C=12C=CC=CC2=CC2=CC=CC=C2C=1\C=C\C1=CC=CC=C1 HCSGQHDONHRJCM-CCEZHUSRSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-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
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 1
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 235000000177 Indigofera tinctoria Nutrition 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- 229920000305 Nylon 6,10 Polymers 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- ZTWQZJLUUZHJGS-UHFFFAOYSA-N Vat Yellow 4 Chemical compound C12=CC=CC=C2C(=O)C2=CC=C3C4=CC=CC=C4C(=O)C4=C3C2=C1C=C4 ZTWQZJLUUZHJGS-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- JWGLGQHIGMBQRK-UHFFFAOYSA-N [3-(4-chlorophenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]-phenylmethanone Chemical class C1=CC(Cl)=CC=C1C1N(C(=O)C=2C=CC=CC=2)N=C(C=2SC=CC=2)C1 JWGLGQHIGMBQRK-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 125000001118 alkylidene group Chemical group 0.000 description 1
- OENHQHLEOONYIE-UKMVMLAPSA-N all-trans beta-carotene Natural products CC=1CCCC(C)(C)C=1/C=C/C(/C)=C/C=C/C(/C)=C/C=C/C=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C OENHQHLEOONYIE-UKMVMLAPSA-N 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910021417 amorphous silicon Inorganic materials 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 239000011648 beta-carotene Substances 0.000 description 1
- TUPZEYHYWIEDIH-WAIFQNFQSA-N beta-carotene Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C)C=CC=C(/C)C=CC2=CCCCC2(C)C TUPZEYHYWIEDIH-WAIFQNFQSA-N 0.000 description 1
- 235000013734 beta-carotene Nutrition 0.000 description 1
- 229960002747 betacarotene Drugs 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- UUWRXRHMQFTLIQ-UHFFFAOYSA-M bis(2-chloroethyl)-[4-(2,6-diphenylthiopyran-4-ylidene)cyclohexa-2,5-dien-1-ylidene]azanium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.C1=CC(=[N+](CCCl)CCCl)C=CC1=C1C=C(C=2C=CC=CC=2)SC(C=2C=CC=CC=2)=C1 UUWRXRHMQFTLIQ-UHFFFAOYSA-M 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000012461 cellulose resin Substances 0.000 description 1
- HGAZMNJKRQFZKS-UHFFFAOYSA-N chloroethene;ethenyl acetate Chemical compound ClC=C.CC(=O)OC=C HGAZMNJKRQFZKS-UHFFFAOYSA-N 0.000 description 1
- JPBGLQJDCUZXEF-UHFFFAOYSA-N chromenylium Chemical compound [O+]1=CC=CC2=CC=CC=C21 JPBGLQJDCUZXEF-UHFFFAOYSA-N 0.000 description 1
- 229920006026 co-polymeric resin Polymers 0.000 description 1
- 239000011247 coating layer Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 229920006242 ethylene acrylic acid copolymer Polymers 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229940097275 indigo Drugs 0.000 description 1
- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000007760 metering rod coating Methods 0.000 description 1
- 239000000113 methacrylic resin Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002717 polyvinylpyridine Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- LLBIOIRWAYBCKK-UHFFFAOYSA-N pyranthrene-8,16-dione Chemical compound C12=CC=CC=C2C(=O)C2=CC=C3C=C4C5=CC=CC=C5C(=O)C5=C4C4=C3C2=C1C=C4C=C5 LLBIOIRWAYBCKK-UHFFFAOYSA-N 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229920005573 silicon-containing polymer Polymers 0.000 description 1
- 229920002545 silicone oil Polymers 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
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical class C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- OENHQHLEOONYIE-JLTXGRSLSA-N β-Carotene Chemical compound CC=1CCCC(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C OENHQHLEOONYIE-JLTXGRSLSA-N 0.000 description 1
Description
〔産業上の利用分野〕
本発明は電子写真感光体に関し、詳しくは改善
された電子写真特性を与える低分子の有機光導電
体を有する電子写真感光体に関するものである。
〔従来技術〕
従来、電子写真感光体にはセレン、酸化亜鉛お
よび硫化カドミウム等の無機光導電性材料が広く
使用されているが、近年有機光導電性材料を電子
写真感光体として用いる研究が活発に行われて来
ている。ここで電子写真感光体に要求される基本
的な特性としては、１）暗所においてコロナ放電
等により適当な電位に帯電されること、２）暗所
における帯電保持率がよいこと、３）光の照射に
より速やかに電荷を放電すること、４）光の照射
後の残留電位が少ないこと等が挙げられる。
従来の、セレン、酸化亜鉛及び硫化カドミウム
等の無機光電性材料を用いた電子写真感光体は基
本的な特性はある程度備えているけれども成膜性
が困難である、可撓性が悪い、製造コストが高
い、など製造上の問題を抱えている。更に無機光
電性材料は一般的に毒性が強く、これらの面から
も無機物質から有機物質の感光体への使用が望ま
れている。一般的に有機系化合物は無機系化合物
に比べ軽量で成膜性及び可撓性に優れ、製造コス
トも低く、更には毒性も弱い等の利点を有してお
り、近年有機化合物を用いた電子写真感光体が数
多く提案され実用化されている。
今まで有機系の電子写真感光体の代表的なもの
としてはポリ−Ｎ−ビニルカルバゾールをはじめ
とする各種の有機光電性ポリマーが提案されて来
たが、これらのポリマーは無機系光導電性材料に
比べ軽量性、成膜性などの点では優れているが、
感度、耐久性、環境変化による安定性及び機械的
強度等の点で無機系光導電材料に比べ劣つている
ため実用化が困難であつた。また、米国特許第
4150987号公報などに開示のヒドラゾン化合物、
米国特許第3837851号公報などに記載のトリアリ
ールピラゾリン化合物、特開昭51−94828号公報、
特開昭51−94829号公報などに記載の９−スチリ
ルアントラセン化合物などの低分子の有機光導電
体が提案されている。この様な低分子の有機光導
電体は、使用するバインダーを適当に選択するこ
とによつて、有機光導電性ポリマーの分野で問題
となつていた成膜性の欠点を解消できる様になつ
たが、感度の点で十分なものとは言えない。
このようなことから、近年感光層を電荷発生層
と電荷輸送層に機能分離させた積層構造体が提案
された。この積層構造を感光層とした電子写真感
光体は、可視光に対する感度、電荷保持力、表面
強度などの点で改善できるようになつた。
電荷輸送材料としてはこれ迄多くの有機化合物
が提案されている。例えば特開昭52−72231号公
報のピラゾリン化合物、米国特許842431号公報及
び特開昭55−52063号公報のヒドラゾン化合物、
特開昭57−195254号公報及び特開昭54−58445号
公報のトリフエニルアミン化合物、特開昭54−
151955号公報及び特開昭58−198043号公報のスチ
ルベン化合物などが開示されている。
しかし従来の低分子の有機化合物を電荷輸送材
料に用いた電子写真感光体では感度、特性が必ら
ずしも十分でなく、また繰り返し帯電及び露光を
行つた際には明部電位と暗部電位の変動が大きく
いまだ改善すべき点がある。
〔発明が解決しようとする問題点〕
本発明の目的は先に述べた従来の感光体のもつ
種々の欠点を解消した電子写真感光体を提供する
ことにある。
本発明の他の目的は製造が容易で、且つ比較的
安価で耐久性にも優れた新規な有機光導電体を提
供することにある。
〔問題点を解決するための手段〕
本発明は導電性支持体上に感光層を有する電子
写真感光体において、感光層が下記一般式〔〕
で示される化合物を含有することを特徴とする。
式中、Ar1およびAr2は置換基を有してもよい
ベンゼン環または芳香族縮合環炭化水素を示す。
ただし、Ar1とAr2のうち少なくとも１つは芳香
族縮合環炭化水素である。芳香族縮合環炭化水素
としてはナフタレン、アントラセン、フエナント
レン、クリセン、ナフタセン等があげられる。
Ar1およびAr2の有してもよい置換基としては
メチル、エチル、プロピル等のアルキル基、メト
キシ、エトキシ、プロポキシ等のアルコキシ基、
フツ素、塩素、臭素等のハロゲン原子等があげら
れる。なおAr1とAr2は同じでも異なつていても
よい。
R1およびR2は水素原子、メチル、エチル、プ
ロピル等のアルキル基、メトキシ、エトキシ、プ
ロポキシ等のアルコキシ基、フツ素、塩素、臭素
等のハロゲン原子等を示す。なおR1とR2は同じ
でも異なつていてもよい。
以下に一般式［］で示される化合物について
その代表例を挙げる。
次に前記化合物の合成例を示す。
（化合物例No.(1)の合成法）
４−ヨードビフエニル5.75g（20.5mmol）、Ｎ−フ
エニル−α−ナフチルアミン3.0g（13.7mmol）、無
水炭酸カリウム2.38g（20.5mmol）及び銅粉1.5gを
ニトロベンゼン30mlに加え攪拌下加熱還流を10時
間行つた。放冷後吸引濾過し濾液を減圧下でニト
ロベンゼンを除去した。残留物をシリカゲルカラ
ムで分離精製を行い目的化合物(1)を3.3g得た（収
率65％）。融点は176.5〜177.5℃であつた。元素
分析はC28H21Ｎとして以下の通りである。
Ｃ（％） Ｈ（％） Ｎ（％）
計算値 90.53 5.70 3.77
実測値 90.48 5.76 3.76
赤外線吸収スペクトル（KBr錠剤法）を第１図
に示した。
以上の様に本発明化合物は製造が容易でかつ安
価に合成できる。
なお、合成例以外の化合物についても、同様な
手法で合成することができる。
本発明の好ましい具体例では、感光層を電荷発
生層と電荷輸送層に機能分離した電子写真感光体
の電荷輸送層に含有される電荷輸送物質として前
記一般式で示される化合物を用いることができ
る。
本発明による電荷輸送層は、前記の一般式で示
される化合物と結着剤とを適当な溶剤に溶解せし
めた溶液を塗布し、乾燥せしめることにより形成
させることが好ましい。ここに用いる結着剤とし
ては、例えばポリアリレート樹脂、ポリスルホン
樹脂、ポリアミド樹脂、アクリル樹脂、アクリロ
ニトリル樹脂、メタクリル樹脂、塩化ビニル樹
脂、酢酸ビニル樹脂、フエノール樹脂、エポキシ
樹脂、ポリエステル樹脂、アルキド樹脂、ポリカ
ーボネート、ポリウレタンあるいは共重合体樹脂
例えばスチレン−ブタジエンコポリマー、スチレ
ン−アクリロニトリルコポリマー、スチレン−マ
レイン酸コポリマーなどを挙げることができる。
また、このような絶縁性ポリマーの他に、ポリビ
ニルカルバゾール、ポリビニルアントラセンやポ
リビニルピレンなどの有機光導電性ポリマーも使
用できる。
この結着剤と本発明の電荷輸送物質との配合割
合は、結着剤100重量部当り電荷輸送物質を10〜
500重量とすることが好ましい。
電荷輸送層は、下述の電荷発生層と電気的に接
続されており、電界の存在下で電荷発生層から注
入された電荷キヤリアを受けとるとともに、これ
らの電荷キヤリアを表面まで輸送できる機能を有
している。この際、この電荷輸送層は、電荷発生
層の上に積層されていてもよく、またその下に積
層されていてもよい。しかし、電荷輸送層は、電
荷発生層の上に積層されていることが望ましい。
この電荷輸送層は、電荷キヤリアを輸送できる限
界があるので、必要以上に膜厚を厚くすることが
できない。一般的には、5μm〜40μmであるが、
好ましい範囲は10μm〜30μmである。
この様な電荷輸送層を形成する際に用いる有機
溶剤は、使用する結着剤の種類によつて異なり、
又は電荷発生層や下述の下引層を溶解しないもの
から選択することが好ましい。具体的な有機溶剤
としては、メタノール、エタノール、イソプロパ
ノールなどのアルコール類、アセトン、メチルエ
チルケトン、シクロヘキサノンなどのケトン類、
Ｎ，Ｎ−ジメチルホルムアミド、Ｎ，Ｎ−ジメチ
ルアセトアミドなどのアミド類、ジメチルスルホ
キシドなどのスルホキシド類、テトラヒドロフラ
ン、ジオキサン、エチレングリコールモノメチル
エーテルなどのエーテル類、酢酸メチル、酢酸エ
チルなどのエステル類、クロロホルム、塩化メチ
レン、ジクロルエチレン、四塩化炭素、トリクロ
ルエチレンなどの脂肪族ハロゲン化炭化水素類あ
るいはベンゼン、トルエン、キシレン、モノクロ
ルベンゼン、ジクロルベンゼンなどの芳香族類な
どを用いることができる。
塗工は、浸漬コーテイング法、アプレーコーテ
イング法、マイヤーバーコーテイング法、ブレー
ドコーテイング法などのコーテイング法を用いて
行なうことができる。乾燥は、室温における指触
乾燥後、加熱乾燥する方法が好ましい。加熱乾燥
は、一般的には30℃〜200℃の温度で５分〜２時
間の範囲の時間で、静止または送風下で行なうこ
とが好ましい。
本発明の電荷輸送層には、種々の添加剤を含有
させて用いることもできる。例えば、ジフエニ
ル、ｍ−ターフエニル、ジブチルフタレートなど
の可塑剤、シリコンオイル、グラフト型シリコン
ポリマー、各種フルオロカーボン類などの表面潤
滑剤、ジシアノビニル化合物、カルバゾール誘導
体などの電位安定剤、β−カロチン、Ni錯体、
１，４−ジアザビシクロ［２，２，２］オクタン
などの酸化防止剤などを挙げることができる。
本発明で用いる電荷発生層は、セレン、セレン
−テルル、アモルフアスシリコン等の無機の電荷
発生物質、ピリリウム系染料、チアピリリウム系
染料、アズレニウム系染料、チアシアニン系染
料、キノシアニン系染料、アズレニウム系染料等
のカチオン染料、スクバリリウム塩系染料、フタ
ロシアニン系顔料、アントアントロン系顔料、ジ
ベンズピレンキノン系顔料、ピラントロン系顔料
等の多環キノン顔料、インジゴ系顔料、キナクリ
ドン系顔料、アゾ顔料等の有機電荷発生物質から
選ばれた材料を単独ないしは組合わせて用い、蒸
発層あるいは塗布層として用いることができる。
本発明に使用される上記電荷発生物質のうち、
アゾ顔料は多岐にわたつているが、特に効果の高
いアゾ顔料の代表的構造例を以下に示す。
アゾ顔料の一般式として、下記のように中心骨
格をＡ、
Ａ−（Ｎ＝Ｎ−Cp）o
カプラー部分をCpとして表わせば（ここでｎ
＝２，or3）、まずＡの具体例としては次のような
ものが挙げられる。
また、Cpの具体例としては
（Ｒ：Ｈ，ハロゲン原子，アルコキシ，アルキ
ル，ニトロ等 ｎ：１，２）
（Ｒ：アルキル，
[Industrial Field of Application] The present invention relates to an electrophotographic photoreceptor, and more particularly to an electrophotographic photoreceptor having a low molecular weight organic photoconductor that provides improved electrophotographic properties. [Prior Art] Conventionally, inorganic photoconductive materials such as selenium, zinc oxide, and cadmium sulfide have been widely used for electrophotographic photoreceptors, but in recent years, research has been active in using organic photoconductive materials as electrophotographic photoreceptors. It has been carried out. Here, the basic characteristics required of an electrophotographic photoreceptor are 1) to be charged to an appropriate potential by corona discharge etc. in a dark place, 2) to have good charge retention in a dark place, and 3) to be exposed to light 4) The residual potential after irradiation with light is small. Conventional electrophotographic photoreceptors using inorganic photosensitive materials such as selenium, zinc oxide, and cadmium sulfide have some basic characteristics, but they have difficulties in film formation, poor flexibility, and manufacturing costs. There are manufacturing problems such as high Furthermore, inorganic photosensitive materials are generally highly toxic, and from this point of view, it is desired to use organic materials instead of inorganic materials for photoreceptors. In general, organic compounds have advantages over inorganic compounds, such as being lightweight, superior in film formability and flexibility, low manufacturing costs, and low toxicity. Many photographic photoreceptors have been proposed and put into practical use. Until now, various organic photoconductive polymers such as poly-N-vinylcarbazole have been proposed as typical organic electrophotographic photoreceptors, but these polymers are not compatible with inorganic photoconductive materials. Although it is superior in terms of light weight and film formability compared to
It has been difficult to put it into practical use because it is inferior to inorganic photoconductive materials in terms of sensitivity, durability, stability against environmental changes, mechanical strength, etc. Additionally, U.S. Patent No.
Hydrazone compounds disclosed in Publication No. 4150987, etc.
Triarylpyrazoline compounds described in U.S. Pat. No. 3,837,851, etc., JP-A-51-94828,
Low-molecular organic photoconductors such as 9-styrylanthracene compounds described in JP-A-51-94829 have been proposed. By appropriately selecting the binder used, such low-molecular-weight organic photoconductors can overcome the film-forming problems that had been a problem in the field of organic photoconductive polymers. However, it cannot be said to be sufficient in terms of sensitivity. For these reasons, a laminated structure in which the photosensitive layer is functionally separated into a charge generation layer and a charge transport layer has been proposed in recent years. Electrophotographic photoreceptors using this laminated structure as a photosensitive layer can now be improved in terms of sensitivity to visible light, charge retention, surface strength, and the like. Many organic compounds have been proposed as charge transport materials. For example, the pyrazoline compound disclosed in JP-A No. 52-72231, the hydrazone compound disclosed in U.S. Patent No. 842431 and JP-A-55-52063,
Triphenylamine compounds of JP-A-57-195254 and JP-A-54-58445, JP-A-54-
Stilbene compounds and the like are disclosed in JP-A No. 151955 and JP-A-58-198043. However, conventional electrophotographic photoreceptors using low-molecular-weight organic compounds as charge transport materials do not always have sufficient sensitivity and characteristics, and when repeatedly charged and exposed, the bright area potential and dark area potential There are large fluctuations and there are still areas that need improvement. [Problems to be Solved by the Invention] An object of the present invention is to provide an electrophotographic photoreceptor that eliminates the various drawbacks of the conventional photoreceptors mentioned above. Another object of the present invention is to provide a novel organic photoconductor that is easy to manufacture, relatively inexpensive, and has excellent durability. [Means for Solving the Problems] The present invention provides an electrophotographic photoreceptor having a photosensitive layer on a conductive support, in which the photosensitive layer has the following general formula []
It is characterized by containing the compound represented by. In the formula, Ar 1 and Ar 2 represent a benzene ring or an aromatic condensed ring hydrocarbon which may have a substituent.
However, at least one of Ar 1 and Ar 2 is an aromatic condensed ring hydrocarbon. Examples of aromatic condensed ring hydrocarbons include naphthalene, anthracene, phenanthrene, chrysene, and naphthacene. Examples of substituents that Ar 1 and Ar 2 may have include alkyl groups such as methyl, ethyl, and propyl; alkoxy groups such as methoxy, ethoxy, and propoxy;
Examples include halogen atoms such as fluorine, chlorine, and bromine. Note that Ar 1 and Ar 2 may be the same or different. R 1 and R 2 represent a hydrogen atom, an alkyl group such as methyl, ethyl, or propyl, an alkoxy group such as methoxy, ethoxy, or propoxy, or a halogen atom such as fluorine, chlorine, or bromine. Note that R 1 and R 2 may be the same or different. Representative examples of compounds represented by the general formula [] are listed below. Next, a synthesis example of the above compound will be shown. (Synthesis method of compound example No. (1)) 4-iodobiphenyl 5.75g (20.5mmol), N-phenyl-α-naphthylamine 3.0g (13.7mmol), anhydrous potassium carbonate 2.38g (20.5mmol), and copper powder 1.5g was added to 30 ml of nitrobenzene and heated under reflux with stirring for 10 hours. After cooling, the mixture was filtered under suction, and nitrobenzene was removed from the filtrate under reduced pressure. The residue was separated and purified using a silica gel column to obtain 3.3 g of target compound (1) (yield 65%). The melting point was 176.5-177.5°C. The elemental analysis as C 28 H 21 N is as follows. C (%) H (%) N (%) Calculated value 90.53 5.70 3.77 Actual value 90.48 5.76 3.76 The infrared absorption spectrum (KB r tablet method) is shown in FIG. As described above, the compound of the present invention is easy to produce and can be synthesized at low cost. Note that compounds other than those in the synthesis example can also be synthesized using the same method. In a preferred embodiment of the present invention, a compound represented by the above general formula can be used as a charge transport substance contained in the charge transport layer of an electrophotographic photoreceptor in which the photosensitive layer is functionally separated into a charge generation layer and a charge transport layer. . The charge transport layer according to the present invention is preferably formed by applying a solution prepared by dissolving the compound represented by the above general formula and a binder in an appropriate solvent and drying the solution. Examples of the binder used here include polyarylate resin, polysulfone resin, polyamide resin, acrylic resin, acrylonitrile resin, methacrylic resin, vinyl chloride resin, vinyl acetate resin, phenol resin, epoxy resin, polyester resin, alkyd resin, and polycarbonate. , polyurethane or copolymer resins such as styrene-butadiene copolymer, styrene-acrylonitrile copolymer, styrene-maleic acid copolymer, and the like.
In addition to such insulating polymers, organic photoconductive polymers such as polyvinylcarbazole, polyvinylanthracene, and polyvinylpyrene can also be used. The blending ratio of this binder and the charge transport substance of the present invention is 10 to 10 parts by weight of the charge transport substance per 100 parts by weight of the binder.
It is preferable to set it as 500 weight. The charge transport layer is electrically connected to the charge generation layer described below, and has the function of receiving charge carriers injected from the charge generation layer in the presence of an electric field and transporting these charge carriers to the surface. are doing. At this time, this charge transport layer may be laminated on or under the charge generation layer. However, it is desirable that the charge transport layer is laminated on the charge generation layer.
Since this charge transport layer has a limit in its ability to transport charge carriers, it cannot be made thicker than necessary. Generally, it is 5 μm to 40 μm, but
The preferred range is 10 μm to 30 μm. The organic solvent used when forming such a charge transport layer varies depending on the type of binder used.
Alternatively, it is preferable to select a material that does not dissolve the charge generation layer or the subbing layer described below. Specific organic solvents include alcohols such as methanol, ethanol, and isopropanol; ketones such as acetone, methyl ethyl ketone, and cyclohexanone;
Amides such as N,N-dimethylformamide and N,N-dimethylacetamide, sulfoxides such as dimethyl sulfoxide, ethers such as tetrahydrofuran, dioxane, and ethylene glycol monomethyl ether, esters such as methyl acetate and ethyl acetate, chloroform, Aliphatic halogenated hydrocarbons such as methylene chloride, dichloroethylene, carbon tetrachloride, trichlorethylene, etc., or aromatics such as benzene, toluene, xylene, monochlorobenzene, dichlorobenzene, etc. can be used. Coating can be carried out using coating methods such as dip coating, spray coating, Meyer bar coating, and blade coating. For drying, it is preferable to dry to the touch at room temperature and then heat dry. Heat drying is generally preferably carried out at a temperature of 30° C. to 200° C. for a period of 5 minutes to 2 hours, either stationary or under ventilation. The charge transport layer of the present invention may contain various additives. For example, plasticizers such as diphenyl, m-terphenyl, and dibutyl phthalate, silicone oil, grafted silicone polymers, surface lubricants such as various fluorocarbons, dicyanovinyl compounds, potential stabilizers such as carbazole derivatives, β-carotene, and Ni complexes. ,
Examples include antioxidants such as 1,4-diazabicyclo[2,2,2]octane. The charge generating layer used in the present invention includes inorganic charge generating substances such as selenium, selenium-tellurium, amorphous silicon, pyrylium dyes, thiapyrylium dyes, azulenium dyes, thiacyanine dyes, quinocyanine dyes, azulenium dyes, etc. organic charge generation in polycyclic quinone pigments such as cationic dyes, squbarium salt dyes, phthalocyanine pigments, anthorone pigments, dibenzpyrenequinone pigments, and pyranthrone pigments, indigo pigments, quinacridone pigments, and azo pigments. Selected materials can be used alone or in combination as the evaporation layer or coating layer. Among the charge generating substances used in the present invention,
Although there are a wide variety of azo pigments, typical structural examples of particularly effective azo pigments are shown below. The general formula of an azo pigment is as follows, where the central skeleton is represented by A, A-(N=N-Cp) o coupler part is represented by Cp (where n
=2, or3), first, the following are specific examples of A: Also, as a specific example of Cp, (R: H, halogen atom, alkoxy, alkyl, nitro, etc. n: 1, 2) (R: alkyl,
【式】
（R′：Ｈ，ハロゲン原子，アルコキシ，アル
キル，ニトロ等））
（Ｒ：Ｈ，ハロゲン原子，アルコキシ，アルキ
ル，ニトロ等）
（Ｒ：アルキル，アリール等）
（R1，R2：Ｈ，ハロゲン原子，アルコキシ，
アルキル，ニトロ等 ｎ：１，２）
等が挙げられる。これら中心骨格Ａ及びカプラー
Cpは適宜組合せにより電荷発生物質となる顔料
を形成する。
電荷発生層は、前述の電荷発生物質を適当な結
着剤に分散させ、これを支持体の上に塗工するこ
とによつて形成でき、また、真空蒸着装置により
蒸着膜を形成することによつて得ることができ
る。上記結着剤としては広範な絶縁性樹脂から選
択でき、また、ポリ−Ｎ−ビニルカルバゾール、
ポリビニルアントラセンやポリビニルピレンなど
の有機光導電性ポリマーから選択できる。好まし
くは、ポリビニルブチラール、ポリアリレート
（ビスフエノールＡとフタル酸の縮重合体など）、
ポリカーボネート、ポリエステル、フエノキシ樹
脂、ポリ酢酸ビニル、アクリル樹脂、ポリアクリ
ルアミド樹脂、ポリアミド、ポリビニルピリジ
ン、セルロース系樹脂、ウレタン樹脂、エポキシ
樹脂、カゼイン、ポリビニルアルコール、ピリビ
ニルピロリドンなどの絶縁性樹脂を挙げることが
できる。
電荷発生層中に含有する樹脂は、80重量％以
下、好ましくは40重量％以下が適している。塗工
の際に用いる有機溶剤としては、メタノール、エ
タノール、イソプロパノールなどのアルコール
類、アセトン、メチルエチルケトン、シクロヘキ
サノンなどのケトン類、Ｎ，Ｎ−ジメチルホルム
アミド、Ｎ，Ｎ−ジメチルアセトアミドなどのア
ミド類、ジメチルスルホキシドなどのスルホキシ
ド類、テトラヒドロフラン、ジオキサン、エチレ
ングリコールモノメチルエーテルなどのエーテル
類、酢酸メチル、酢酸エチルなどのエステル類、
クロロホルム、塩化メチレン、ジクロルエチレ
ン、四塩化炭素、トリクロルエチレンなどの脂肪
族ハロゲン化炭化水素類あるいはベンゼン、トル
エン、キシレン、モノクロルベンゼン、ジクロル
ベンゼンなどの芳香族類などを用いることができ
る。
電荷発生層は、十分な吸光度を得るために、で
きる限り多くの前記有機光導電体を含有し、且つ
発生した電荷キヤリアの寿命内にキヤリアを電荷
輸送層へ注入するために、薄膜層、例えば5μm以
下、好ましくは0.01μm〜1μmの膜厚をもつ薄膜
層とすることが好ましい。このことは、入射光量
の大部分が電荷発生層で吸収されて、多くの電荷
キヤリアを生成すること、さらに発生した電荷キ
ヤリアを再結合や捕獲（トラツプ）により失活す
ることなく電荷輸送層に注入する必要があること
に帰因している。
この様な電荷発生層と電荷輸送層の積層構造か
らなる感光層は、導電性支持体の上に設けられ
る。導電性支持体としては、支持体自体が導電性
をもつもの、例えばアルミニウム、アルミニウム
合金、銅、亜鉛、ステンレスなどを用いることが
でき、その他にアルミニウム、アルミニウム合
金、酸化インジウム、酸化錫、酸化インジウム−
酸化錫合金などを真空蒸着法によつて被膜形成さ
れた層を有するプラスチツク、導電性粒子（例え
ば、アルミニウム粉末、酸化チタン、酸化錫、酸
化亜鉛、カーボンブラツク、銀粒子など）を適当
なバインダーとともにプラスチツク又は前記金属
支持体の上に被覆した支持体、導電性粒子をプラ
スチツクや紙に含浸した支持体や導電性ポリマー
を有するプラスチツクなどを用いることができ
る。
導電性支持体と感光層の中間に、バリヤー機能
と接着機能をもつ下引層を設けることもできる。
下引層は、カゼイン、ポリビニルアルコール、ニ
トロセルロース、エチレン−アクリル酸コポリマ
ー、ポリアミド（ナイロン６、ナイロン66、ナイ
ロン610、共重合ナイロン、アルコキシメチル化
ナイロンなど）、ポリウレタン、ゼラチン、酸化
アルミニウムなどによつて形成できる。
下引層の膜厚は、0.1μm〜5μm、好ましくは
0.5μm〜3μmが適当である。
本発明の別の具体例では、前述のジスアゾ顔料
あるいは、米国特許第3554745号、同第3567438
号、同第3586500号公報などに開示のピリリウム
染料、チアピリリウム染料、セレナピリリウム染
料、ベンゾピリリウム染料、ベンゾチアピリリウ
ム染料、ナフトピリリウム染料、ナフトチアピリ
リウム染料などの光導電性を有する顔料や染料を
増感剤としても用いることができる。
また、別の具体例では、米国特許第3684502号
公報などに開示のピリリウム染料とアルキリデン
ジアリーレン部分を有する電気絶縁重合体との共
晶錯体を増感剤として用いることもできる。この
共晶錯体は、例えば４−［４−ビス−（２−クロロ
エチル）アミノフエニル］−２，６−ジフエニル
チアピリリウムパークロレートとポリ（４，4′−
イソプロピリデンジフエニレンカーボネート）を
ハロゲン化炭化水素系溶剤（例えばジクロルメタ
ン、クロロホルム、四塩化炭素、１，１−ジクロ
ルエタン、１，２−ジクロルエタン、１，１，２
−トリクロルエタン、クロルベンゼン、ブロモベ
ンゼン、１，２−ジクロルベンゼン）に溶解した
後、これに非極性溶剤（例えば、ヘキサン、オク
タン、デカン、２，２，４−トリメチルベンゼ
ン、リグロインを加えることによつて粒子状共晶
錯体として得られる。この具体例における電子写
真感光体には、スチレン−ブタジエンコポリマ
ー、シリコン樹脂、ビニル樹脂、塩化ビニリデン
−アクリロニトリルコポリマー、スチレン−アク
リロニトリルコポリマー、ビニルアセテート−塩
化ビニルコポリマー、ポリビニルブチラール、ポ
リメチルメタクリレート、ポリ−Ｎ−ブチルメタ
クリレート、ポリエステル類、セルロースエステ
ル類などを結着剤として含有することができる。
本発明の電子写真感光体は、電子写真複写機に
利用するのみならず、レーザープリンター、
CRTプリンター、電子写真式製版システムなど
の電子写真応用分野にも広く用いることができ
る。
以下、本発明を実施例に従つて説明する。
実施例 １
下記構造式
で示されるジスアゾ顔料5gをブチラール樹脂
（ブチラール化度63モル％）2gをシクロヘキサノ
ン100mlに溶解した液とともにサンドミルで24時
間分散し塗工液を調製した。
この塗工液をアルミシート上に乾燥膜厚が
0.2μmとなる様にマイヤーバーで塗布し電荷発生
層を作製した。
次に電荷輸送物質として前記例示化合物No.(4)
10gとポリカーボネート樹脂（重量平均分子量
20000）10gをモノクロルベンゼン70gに溶解し、
この液を先の電荷発生層の上にマイヤーバーで塗
布し乾燥膜厚が20μmの電荷輸送層を設け積層の
電子写真感光体を作製した。
この様にして作製した電子写真感光体を川口電
機（株）製静電複写紙試験装置Model−SP−428
を用いてスタチツク方式で−5KVでコロナ帯電
し、暗所で１秒間保持した後、照度20uxで露
光し帯電特性を調べた。
帯電特性としては、表面電位（V0）と１秒間
暗減衰させた時の電位（V1）を1/2に減衰するに
必要な露光量（Ｅ1/2）を測定した。
さらに、繰り返し使用した時の明部電位と暗部
電位の変動を測定するために、本実施例で作製し
た感光体をPPC複写機（NP−3525：キヤノン
製）の感光ドラム用シリンダーに貼り付けて、同
機で5000枚複写を行ない、初期と5000枚複写後の
明部電位（VL）及び暗部電位（VD）の変動を測
定した。なお、初期のVDとVLは各々−700V、−
200Vとなる様に設定した。その結果を以下に示
す。[Formula] (R': H, halogen atom, alkoxy, alkyl, nitro, etc.)) (R:H, halogen atom, alkoxy, alkyl, nitro, etc.) (R: alkyl, aryl, etc.) (R 1 , R 2 : H, halogen atom, alkoxy,
Examples include alkyl, nitro, etc. (n: 1, 2). These central skeletons A and couplers
Cp forms a pigment that becomes a charge-generating substance by appropriate combination. The charge-generating layer can be formed by dispersing the charge-generating substance described above in a suitable binder and coating it on a support, or by forming a vapor-deposited film using a vacuum evaporation device. You can get it by twisting it. The binder can be selected from a wide range of insulating resins, including poly-N-vinylcarbazole,
It can be selected from organic photoconductive polymers such as polyvinylanthracene and polyvinylpyrene. Preferably, polyvinyl butyral, polyarylate (condensation polymer of bisphenol A and phthalic acid, etc.),
Examples include insulating resins such as polycarbonate, polyester, phenoxy resin, polyvinyl acetate, acrylic resin, polyacrylamide resin, polyamide, polyvinylpyridine, cellulose resin, urethane resin, epoxy resin, casein, polyvinyl alcohol, and pyrivinylpyrrolidone. can. The resin contained in the charge generation layer is suitably 80% by weight or less, preferably 40% by weight or less. Organic solvents used during coating include alcohols such as methanol, ethanol and isopropanol, ketones such as acetone, methyl ethyl ketone and cyclohexanone, amides such as N,N-dimethylformamide and N,N-dimethylacetamide, dimethyl Sulfoxides such as sulfoxide, ethers such as tetrahydrofuran, dioxane, and ethylene glycol monomethyl ether, esters such as methyl acetate and ethyl acetate,
Aliphatic halogenated hydrocarbons such as chloroform, methylene chloride, dichloroethylene, carbon tetrachloride, trichloroethylene, etc., or aromatics such as benzene, toluene, xylene, monochlorobenzene, dichlorobenzene, etc. can be used. The charge generation layer contains as much of said organic photoconductor as possible in order to obtain sufficient absorbance and in order to inject carriers into the charge transport layer during the lifetime of the generated charge carriers, a thin film layer, e.g. It is preferable to form a thin film layer having a thickness of 5 μm or less, preferably 0.01 μm to 1 μm. This means that most of the incident light is absorbed by the charge generation layer, generating many charge carriers, and that the generated charge carriers are not deactivated by recombination or trapping, but are transferred to the charge transport layer. This is due to the need for injection. A photosensitive layer having such a laminated structure of a charge generation layer and a charge transport layer is provided on a conductive support. As the conductive support, materials that are conductive themselves such as aluminum, aluminum alloy, copper, zinc, stainless steel, etc. can be used.In addition, aluminum, aluminum alloy, indium oxide, tin oxide, and indium oxide can be used. −
Plastic having a layer formed of a tin oxide alloy or the like by vacuum evaporation, conductive particles (for example, aluminum powder, titanium oxide, tin oxide, zinc oxide, carbon black, silver particles, etc.) together with a suitable binder. A support coated on a plastic or metal support, a support made of plastic or paper impregnated with conductive particles, a plastic containing a conductive polymer, etc. can be used. A subbing layer having barrier and adhesive functions can also be provided between the conductive support and the photosensitive layer.
The undercoat layer may be made of casein, polyvinyl alcohol, nitrocellulose, ethylene-acrylic acid copolymer, polyamide (nylon 6, nylon 66, nylon 610, copolymerized nylon, alkoxymethylated nylon, etc.), polyurethane, gelatin, aluminum oxide, etc. It can be formed by The thickness of the undercoat layer is 0.1 μm to 5 μm, preferably
0.5 μm to 3 μm is suitable. In another embodiment of the present invention, the aforementioned disazo pigments or
Pigments having photoconductivity such as pyrylium dyes, thiapyrylium dyes, selenapyrylium dyes, benzopyrylium dyes, benzothiapyryllium dyes, naphthopyryllium dyes, and naphthothiapyrylium dyes disclosed in the same publication No. 3586500, etc. Dyes can also be used as sensitizers. In another specific example, a eutectic complex of a pyrylium dye and an electrically insulating polymer having an alkylidene diarylene moiety, as disclosed in US Pat. No. 3,684,502, can also be used as a sensitizer. This eutectic complex is composed of, for example, 4-[4-bis-(2-chloroethyl)aminophenyl]-2,6-diphenylthiapyrylium perchlorate and poly(4,4'-
isopropylidene diphenylene carbonate) in a halogenated hydrocarbon solvent (e.g. dichloromethane, chloroform, carbon tetrachloride, 1,1-dichloroethane, 1,2-dichloroethane, 1,1,2
- trichloroethane, chlorobenzene, bromobenzene, 1,2-dichlorobenzene) and then adding a non-polar solvent (e.g. hexane, octane, decane, 2,2,4-trimethylbenzene, ligroin) thereto. The electrophotographic photoreceptor in this example includes styrene-butadiene copolymer, silicone resin, vinyl resin, vinylidene chloride-acrylonitrile copolymer, styrene-acrylonitrile copolymer, vinyl acetate-vinyl chloride. Copolymers, polyvinyl butyral, polymethyl methacrylate, poly-N-butyl methacrylate, polyesters, cellulose esters, etc. can be contained as a binder.The electrophotographic photoreceptor of the present invention is used in an electrophotographic copying machine. Not only laser printers,
It can also be widely used in electrophotographic applications such as CRT printers and electrophotographic plate making systems. Hereinafter, the present invention will be explained according to examples. Example 1 Structural formula below A coating solution was prepared by dispersing 5 g of the disazo pigment represented by 2 g in a sand mill for 24 hours with a solution obtained by dissolving 2 g of butyral resin (degree of butyralization: 63 mol %) in 100 ml of cyclohexanone. Apply this coating solution on an aluminum sheet until the dry film thickness is
A charge generation layer was prepared by coating with a Mayer bar to a thickness of 0.2 μm. Next, the above-mentioned exemplified compound No. (4) is used as a charge transport material.
10g and polycarbonate resin (weight average molecular weight
20000) dissolved in 70g of monochlorobenzene,
This liquid was applied onto the charge generation layer using a Mayer bar to form a charge transport layer having a dry thickness of 20 μm, thereby producing a laminated electrophotographic photoreceptor. The electrophotographic photoreceptor produced in this way was tested using an electrostatic copying paper tester Model-SP-428 manufactured by Kawaguchi Electric Co., Ltd.
The sample was statically charged with a corona at -5KV using a 1000V, held in a dark place for 1 second, and then exposed to light at an illuminance of 20ux to examine the charging characteristics. As for the charging characteristics, the surface potential (V 0 ) and the exposure amount (E1/2) required to attenuate the potential (V 1 ) by 1/2 when dark decayed for 1 second were measured. Furthermore, in order to measure the fluctuations in bright area potential and dark area potential during repeated use, the photoreceptor fabricated in this example was attached to the photosensitive drum cylinder of a PPC copier (NP-3525, manufactured by Canon). , 5,000 copies were made with the same machine, and the fluctuations in the bright area potential (V L ) and the dark area potential (V D ) were measured at the initial stage and after 5,000 copies were made. Note that the initial V D and V L are -700V and -700V, respectively.
I set it to 200V. The results are shown below.
【表】
実施例 ２〜７、比較例 １〜３
この各実施例においては、前記実施例１で用い
た電荷輸送物質として例示化合物No.(4)の代りに例
示化合物No.(1)，(3)，(8)，(14)，(18)，(19)を用い、
かつ
電荷発生物質として下記構造式
の顔料を用いたほかは、実施例１と同様の方法に
よつて電子写真感光体を作製した。
各感光体の電子写真特性を実施例１と同様の方
法によつて測定した。
また比較のために、下記構造式の化合物を電荷
輸送物質として用いたほかは実施例１と同様の方
法によつて、電子写真感光体を作製し、電子写真
特性を測定した。それぞれの結果を以下に示す。
[Table] Examples 2 to 7, Comparative Examples 1 to 3 In each of these Examples, Exemplary Compound No. (1), Using (3), (8), (14), (18), (19),
And as a charge generating substance, the following structural formula An electrophotographic photoreceptor was produced in the same manner as in Example 1, except that the following pigment was used. The electrophotographic properties of each photoreceptor were measured in the same manner as in Example 1. For comparison, an electrophotographic photoreceptor was prepared in the same manner as in Example 1, except that a compound having the following structural formula was used as a charge transport material, and its electrophotographic properties were measured. The respective results are shown below.
【表】【table】
【表】
以上の結果から明らかなように、本発明化合物
は比較化合物に比べ感度及び耐久時の電位安定性
に優れていることが明らかである。
実施例 ８
アルミ基板上にメトキシメチル化ナイロン樹脂
（数平均分子量32000）5gとアルコール可溶性共
重合ナイロン樹脂（数平均分子量29000）10gを
メタノール95gに溶解した液をマイヤーバーで塗
布し、乾燥後の膜厚が1μmの下引き層を設けた。
次に下記構造式
で示される電荷発生物質10g、ブチラール樹脂
（ブチラール化度63モル％）5gとジオキサン200g
を、ボールミル分散機で48時間分散を行つた。こ
の分散液を先に製造した下引層の上にブレードコ
ーテイング法により塗布し、乾燥後の膜厚が
0.15μmの電荷発生層を作製した。
次に前記例示化合物No.(16)10g、ポリメチルメタ
クリレート樹脂（重量平均分子量50000）10gを
モノクロルベンゼン70gに溶解し、先に形成した
電荷発生層の上にブレードコーテイング法により
塗布し、乾燥後の膜厚が19μmの電荷輸送層を作
製した。
こうして作製した感光体に−5KVのコロナ放
電を行なつた。この時の表面電位を測定した（初
期電位V0）。さらに、この感光体を１秒間暗所で
放置した後の表面電位を測定した。感度は、暗減
衰した後の電位V1を1/2に減衰するに必要な露光
量（E1／２，μJ／cm2）を測定することによつて
評価した。この際、光源としてガリウム／アルミ
ニウム／ヒ素の三元系半導体レーザー（出力：
5mW；発振波長780nm）を用いた。これらの結
果は、次のとおりであつた。
V0：−700V
V1：−694V
Ｅ1/2：0.54μJ／cm2
次に同上の半導体レーザーを備えた反転現像方
式の電子写真方式プリンターであるレーザービー
ムプリンター（LBP−CX：キヤノン製）に上記
感光体をセツトし、実際の画像形成テストを用い
た。条件は以下の通りである。一次帯電後の表面
電位；−700V、像露光後の表面電位；−150V
（露光量2.0μJ／cm2）、転写電位；＋700V、現像剤
極性；負極性、プロセススピード；50mm／sec、
現像条件（現像バイアス）；−450V、像露光スキ
ヤン方式；イメージスキヤン、一次帯電前露光；
50lux・secの赤色全面露光、画像形成はレーザー
ビームを文字信号及び画像信号に従つてラインス
キヤンして行つたが、文字、画像共に良好なプリ
ントが得られた。更に、連続3000枚の画出しを行
つたところ初期から3000枚まで安定した良好なプ
リントが得られた。
実施例 ９
チタニルオキシフタロシアニン10gをジオキサ
ン485gにフエノキシ樹脂5gを溶かした液に加え
てボールミルで２時間分散した。この分散液をア
ルミシート上にマイヤーバーで塗布し、80℃で２
時間乾燥させ、0.5μmの電荷発生層を作製した。
次に前記例示化合物No.(3)10g、ビスフエノールＺ
型ポリカーボネート樹脂（重量平均分子量50000）
10gをモノクロルベンゼン70gに溶解した液を、
先に形成した電荷発生層の上にマイヤーバーで塗
布し、90℃で２時間乾燥させ、19μmの電荷輸送
層を形成した。また比較の為に、下記構造の化合
物を電荷輸送化合物として用い同様の方法により
感光体を作製した。このようにして作製した感光
体を実施例８と同様な方法で測定した。この結果
を次に示す。
[Table] As is clear from the above results, it is clear that the compounds of the present invention are superior in sensitivity and potential stability during durability compared to comparative compounds. Example 8 A solution prepared by dissolving 5 g of methoxymethylated nylon resin (number average molecular weight 32,000) and alcohol-soluble copolymerized nylon resin (10 g) (number average molecular weight 29,000) in 95 g of methanol was applied onto an aluminum substrate using a Mayer bar, and after drying. A subbing layer with a film thickness of 1 μm was provided. Next, the following structural formula 10g of charge generating substance shown in , 5g of butyral resin (degree of butyralization 63 mol%) and 200g of dioxane
was dispersed for 48 hours using a ball mill dispersion machine. This dispersion was applied onto the previously prepared undercoat layer using the blade coating method, and the film thickness after drying was
A charge generation layer of 0.15 μm was fabricated. Next, 10 g of the above-mentioned exemplified compound No. (16) and 10 g of polymethyl methacrylate resin (weight average molecular weight 50,000) were dissolved in 70 g of monochlorobenzene, and the solution was coated on the previously formed charge generation layer by a blade coating method, and after drying. A charge transport layer with a thickness of 19 μm was fabricated. A corona discharge of -5 KV was applied to the photoreceptor thus prepared. The surface potential at this time was measured (initial potential V 0 ). Furthermore, the surface potential of this photoreceptor was measured after it was left in a dark place for 1 second. Sensitivity was evaluated by measuring the amount of exposure (E1/2, μJ/cm 2 ) required to attenuate the potential V 1 after dark decay to 1/2. At this time, the light source was a gallium/aluminum/arsenic ternary semiconductor laser (output:
5 mW; oscillation wavelength 780 nm). These results were as follows. V 0 : -700V V 1 : -694V E1/2: 0.54μJ/cm Second , the laser beam printer (LBP-CX: manufactured by Canon), which is a reversal development type electrophotographic printer equipped with the same semiconductor laser as above, was used. The above photoreceptor was set up and used in an actual image forming test. The conditions are as follows. Surface potential after primary charging: -700V, surface potential after image exposure: -150V
(Exposure amount: 2.0μJ/cm 2 ), Transfer potential: +700V, Developer polarity: Negative polarity, Process speed: 50mm/sec,
Development conditions (development bias): -450V, image exposure scan method; image scan, exposure before primary charging;
Full red exposure was performed at 50 lux·sec, and image formation was performed by line scanning a laser beam in accordance with character and image signals, and good prints were obtained for both characters and images. Furthermore, when 3,000 images were printed continuously, stable and good prints were obtained from the initial stage up to 3,000 images. Example 9 10 g of titanyloxyphthalocyanine was added to a solution prepared by dissolving 5 g of phenoxy resin in 485 g of dioxane, and dispersed in a ball mill for 2 hours. This dispersion was applied onto an aluminum sheet using a Mayer bar, and heated to 80℃ for 2 hours.
It was dried for an hour to produce a charge generation layer of 0.5 μm.
Next, 10 g of the exemplified compound No. (3), bisphenol Z
Type polycarbonate resin (weight average molecular weight 50000)
A solution of 10g dissolved in 70g of monochlorobenzene,
It was coated on the previously formed charge generation layer using a Mayer bar and dried at 90° C. for 2 hours to form a charge transport layer of 19 μm. For comparison, a photoreceptor was prepared in the same manner using a compound having the structure shown below as a charge transporting compound. The thus produced photoreceptor was measured in the same manner as in Example 8. The results are shown below.
以上説明したように、本発明によるトリアリー
ルアミン化合物を含有する電子写真感光体は高感
度であり、また繰返し帯電・露光による連続画像
形成に際して明部電位と暗部電位の変動が小さい
耐久性に優れた電子写真感光体を提供できるもの
である。
As explained above, the electrophotographic photoreceptor containing the triarylamine compound according to the present invention has high sensitivity, and also has excellent durability with small fluctuations in bright area potential and dark area potential during continuous image formation by repeated charging and exposure. Accordingly, it is possible to provide an electrophotographic photoreceptor.
第１図は、合成例で得られた化合物例No.(1)の赤
外吸収スペクトル図（KBr錠剤法）である。
FIG. 1 is an infrared absorption spectrum diagram (KBr tablet method) of Compound Example No. (1) obtained in Synthesis Example.
Claims (1)
光体において、感光層が下記一般式で示されるト
リアリールアミン化合物を含有することを特徴と
する電子写真感光体。 一般式〔〕 （式中、Ar1およびAr2は置換基を有してもよ
いベンゼン環または芳香族縮合環炭化水素を示
す。ただし、Ar1とAr2のうち少なくとも１つは
芳香族縮合環炭化水素である。R1およびR2は水
素原子、アルキル基、アルコキシ基またはハロゲ
ン原子を示す。）[Scope of Claims] 1. An electrophotographic photoreceptor having a photosensitive layer on a conductive support, wherein the photosensitive layer contains a triarylamine compound represented by the following general formula. General formula [] (In the formula, Ar 1 and Ar 2 represent a benzene ring or an aromatic condensed ring hydrocarbon which may have a substituent. However, at least one of Ar 1 and Ar 2 is an aromatic condensed ring hydrocarbon. (R 1 and R 2 represent a hydrogen atom, an alkyl group, an alkoxy group, or a halogen atom.)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63330987A JPH02178666A (en) | 1988-12-29 | 1988-12-29 | Electrophotographic sensitive body |
| EP89124079A EP0376311B1 (en) | 1988-12-29 | 1989-12-28 | Photosensitive member for electrophotography |
| CA002006861A CA2006861C (en) | 1988-12-29 | 1989-12-28 | Photosensitive member for electrophotography |
| DE68922083T DE68922083T2 (en) | 1988-12-29 | 1989-12-28 | Photosensitive element for electrophotography. |
| AU47369/89A AU604429B2 (en) | 1988-12-29 | 1989-12-29 | Photosensitive member for electrophotography |
| US07/945,576 US5262261A (en) | 1988-12-29 | 1992-09-16 | Photosensitive member for electrophotography |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63330987A JPH02178666A (en) | 1988-12-29 | 1988-12-29 | Electrophotographic sensitive body |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02178666A JPH02178666A (en) | 1990-07-11 |
| JPH0516018B2 true JPH0516018B2 (en) | 1993-03-03 |
Family
ID=18238570
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63330987A Granted JPH02178666A (en) | 1988-12-29 | 1988-12-29 | Electrophotographic sensitive body |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH02178666A (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5495049A (en) * | 1993-03-22 | 1996-02-27 | Fuji Xerox Co., Ltd. | Triarylamine compounds useful in electrophotographic photoreceptors |
| JPH07233106A (en) * | 1994-02-23 | 1995-09-05 | Fuji Xerox Co Ltd | Production of monoiodinated aromatic compound |
| DE69704239T2 (en) * | 1996-08-08 | 2001-08-09 | Canon Kk | Electrophotographic photosensitive member, process cartridge and electrophotographic device containing this member |
| US7138555B2 (en) | 2004-04-20 | 2006-11-21 | Xerox Corporation | Process for preparing iodoaromatic compounds and using the same |
| JP5712858B2 (en) * | 2011-08-10 | 2015-05-07 | 三菱化学株式会社 | Electrophotographic photosensitive member containing triarylamine compound, electrophotographic photosensitive member cartridge, and image forming apparatus |
| JP6788335B2 (en) | 2014-08-11 | 2020-11-25 | 三星ディスプレイ株式會社Ｓａｍｓｕｎｇ Ｄｉｓｐｌａｙ Ｃｏ．，Ｌｔｄ． | Monoamine materials for organic electroluminescence devices and organic electroluminescence devices using them |
-
1988
- 1988-12-29 JP JP63330987A patent/JPH02178666A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH02178666A (en) | 1990-07-11 |
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| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |