JPH0368952A - Electrophotographic sensitive body - Google Patents
Electrophotographic sensitive bodyInfo
- Publication number
- JPH0368952A JPH0368952A JP20395089A JP20395089A JPH0368952A JP H0368952 A JPH0368952 A JP H0368952A JP 20395089 A JP20395089 A JP 20395089A JP 20395089 A JP20395089 A JP 20395089A JP H0368952 A JPH0368952 A JP H0368952A
- Authority
- JP
- Japan
- Prior art keywords
- group
- photoreceptor
- bismesoionic
- photosensitive layer
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 125000001424 substituent group Chemical group 0.000 claims abstract description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 3
- 108091008695 photoreceptors Proteins 0.000 claims description 57
- 239000000126 substance Substances 0.000 claims description 14
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 5
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 4
- 239000011230 binding agent Substances 0.000 abstract description 21
- 230000035945 sensitivity Effects 0.000 abstract description 12
- 239000006185 dispersion Substances 0.000 abstract description 8
- 230000001105 regulatory effect Effects 0.000 abstract 2
- -1 (3,3'-dimethylbiphenyl)-4,4'-diyl group Chemical group 0.000 description 82
- 239000010410 layer Substances 0.000 description 33
- 230000032258 transport Effects 0.000 description 27
- 150000001875 compounds Chemical class 0.000 description 23
- 239000000463 material Substances 0.000 description 15
- 239000002800 charge carrier Substances 0.000 description 13
- 238000000576 coating method Methods 0.000 description 11
- 239000000243 solution Substances 0.000 description 10
- 239000011248 coating agent Substances 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000001035 drying Methods 0.000 description 7
- 239000000975 dye Substances 0.000 description 7
- 125000003396 thiol group Chemical group [H]S* 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 239000006163 transport media Substances 0.000 description 6
- 150000002484 inorganic compounds Chemical class 0.000 description 5
- 229910010272 inorganic material Inorganic materials 0.000 description 5
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 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 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 206010034972 Photosensitivity reaction Diseases 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- 239000004014 plasticizer Substances 0.000 description 3
- 229920006267 polyester film Polymers 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 3
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 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
- 239000004793 Polystyrene Substances 0.000 description 2
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 229920000180 alkyd Polymers 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 125000004103 aminoalkyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 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
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000010419 fine particle Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 229920000126 latex Polymers 0.000 description 2
- 239000004816 latex Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- JGOAZQAXRONCCI-SDNWHVSQSA-N n-[(e)-benzylideneamino]aniline Chemical compound C=1C=CC=CC=1N\N=C\C1=CC=CC=C1 JGOAZQAXRONCCI-SDNWHVSQSA-N 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229920001568 phenolic resin Polymers 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 230000036211 photosensitivity Effects 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 2
- 229920005668 polycarbonate resin Polymers 0.000 description 2
- 239000004431 polycarbonate resin Substances 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920001225 polyester resin Polymers 0.000 description 2
- 239000004645 polyester resin Substances 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical class C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 2
- 229910052711 selenium Inorganic materials 0.000 description 2
- 239000011669 selenium Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- NLDYACGHTUPAQU-UHFFFAOYSA-N tetracyanoethylene Chemical group N#CC(C#N)=C(C#N)C#N NLDYACGHTUPAQU-UHFFFAOYSA-N 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 1
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 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
- XJKSTNDFUHDPQJ-UHFFFAOYSA-N 1,4-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=C(C=2C=CC=CC=2)C=C1 XJKSTNDFUHDPQJ-UHFFFAOYSA-N 0.000 description 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- KTXUOWUHFLBZPW-UHFFFAOYSA-N 1-chloro-3-(3-chlorophenyl)benzene Chemical group ClC1=CC=CC(C=2C=C(Cl)C=CC=2)=C1 KTXUOWUHFLBZPW-UHFFFAOYSA-N 0.000 description 1
- PXPBDJVBNWDUFM-UHFFFAOYSA-N 2,3,4,6-tetranitrophenol Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C([N+]([O-])=O)=C1[N+]([O-])=O PXPBDJVBNWDUFM-UHFFFAOYSA-N 0.000 description 1
- JOERSAVCLPYNIZ-UHFFFAOYSA-N 2,4,5,7-tetranitrofluoren-9-one Chemical compound O=C1C2=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C2C2=C1C=C([N+](=O)[O-])C=C2[N+]([O-])=O JOERSAVCLPYNIZ-UHFFFAOYSA-N 0.000 description 1
- VHQGURIJMFPBKS-UHFFFAOYSA-N 2,4,7-trinitrofluoren-9-one Chemical compound [O-][N+](=O)C1=CC([N+]([O-])=O)=C2C3=CC=C([N+](=O)[O-])C=C3C(=O)C2=C1 VHQGURIJMFPBKS-UHFFFAOYSA-N 0.000 description 1
- SJNWVJGWEJCMEY-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethanol;phthalic acid Chemical compound OCCOCCO.OC(=O)C1=CC=CC=C1C(O)=O SJNWVJGWEJCMEY-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- SCGKCGMVFXMMSF-LYBHJNIJSA-N 2-[(E)-(diphenylhydrazinylidene)methyl]-N,N-diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1\C=N\N(C=1C=CC=CC=1)C1=CC=CC=C1 SCGKCGMVFXMMSF-LYBHJNIJSA-N 0.000 description 1
- IJGGFSGEISKIHB-UHFFFAOYSA-N 2-[(diphenylhydrazinylidene)methyl]-n,n-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1C=NN(C=1C=CC=CC=1)C1=CC=CC=C1 IJGGFSGEISKIHB-UHFFFAOYSA-N 0.000 description 1
- 125000005999 2-bromoethyl group Chemical group 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- WGRSVHBSCVGKDP-UHFFFAOYSA-N 2-ethyl-9h-carbazole-1-carbaldehyde Chemical compound C1=CC=C2C3=CC=C(CC)C(C=O)=C3NC2=C1 WGRSVHBSCVGKDP-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- WUPHOULIZUERAE-UHFFFAOYSA-N 3-(oxolan-2-yl)propanoic acid Chemical compound OC(=O)CCC1CCCO1 WUPHOULIZUERAE-UHFFFAOYSA-N 0.000 description 1
- OGGKVJMNFFSDEV-UHFFFAOYSA-N 3-methyl-n-[4-[4-(n-(3-methylphenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 OGGKVJMNFFSDEV-UHFFFAOYSA-N 0.000 description 1
- RXXCIBALSKQCAE-UHFFFAOYSA-N 3-methylbutoxymethylbenzene Chemical compound CC(C)CCOCC1=CC=CC=C1 RXXCIBALSKQCAE-UHFFFAOYSA-N 0.000 description 1
- IICCLYANAQEHCI-UHFFFAOYSA-N 4,5,6,7-tetrachloro-3',6'-dihydroxy-2',4',5',7'-tetraiodospiro[2-benzofuran-3,9'-xanthene]-1-one Chemical compound O1C(=O)C(C(=C(Cl)C(Cl)=C2Cl)Cl)=C2C21C1=CC(I)=C(O)C(I)=C1OC1=C(I)C(O)=C(I)C=C21 IICCLYANAQEHCI-UHFFFAOYSA-N 0.000 description 1
- UESSERYYFWCTBU-UHFFFAOYSA-N 4-(n-phenylanilino)benzaldehyde Chemical compound C1=CC(C=O)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 UESSERYYFWCTBU-UHFFFAOYSA-N 0.000 description 1
- PGDARWFJWJKPLY-UHFFFAOYSA-N 4-[2-[3-[4-(diethylamino)phenyl]-2-phenyl-1,3-dihydropyrazol-5-yl]ethenyl]-n,n-diethylaniline Chemical compound C1=CC(N(CC)CC)=CC=C1C=CC1=CC(C=2C=CC(=CC=2)N(CC)CC)N(C=2C=CC=CC=2)N1 PGDARWFJWJKPLY-UHFFFAOYSA-N 0.000 description 1
- PLAZXGNBGZYJSA-UHFFFAOYSA-N 9-ethylcarbazole Chemical compound C1=CC=C2N(CC)C3=CC=CC=C3C2=C1 PLAZXGNBGZYJSA-UHFFFAOYSA-N 0.000 description 1
- VIJYEGDOKCKUOL-UHFFFAOYSA-N 9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 VIJYEGDOKCKUOL-UHFFFAOYSA-N 0.000 description 1
- LSZJZNNASZFXKN-UHFFFAOYSA-N 9-propan-2-ylcarbazole Chemical compound C1=CC=C2N(C(C)C)C3=CC=CC=C3C2=C1 LSZJZNNASZFXKN-UHFFFAOYSA-N 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- FRAGTFSDXRAQCO-UHFFFAOYSA-N C=C1CN(C2=CC=CC=C12)N.C(C)N1C2=CC=CC=C2C=2C=CC=CC12 Chemical compound C=C1CN(C2=CC=CC=C12)N.C(C)N1C2=CC=CC=C2C=2C=CC=CC12 FRAGTFSDXRAQCO-UHFFFAOYSA-N 0.000 description 1
- GDXLHMIKVIFRSD-UHFFFAOYSA-N C=C1CN(C2=CCCCC2C1)N.C(C)N1C2=CC=CC=C2C=2C=CC=CC12 Chemical compound C=C1CN(C2=CCCCC2C1)N.C(C)N1C2=CC=CC=C2C=2C=CC=CC12 GDXLHMIKVIFRSD-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical group O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- 239000000020 Nitrocellulose Substances 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
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 229920002433 Vinyl chloride-vinyl acetate copolymer Polymers 0.000 description 1
- MUBKMWFYVHYZAI-UHFFFAOYSA-N [Al].[Cu].[Zn] Chemical compound [Al].[Cu].[Zn] MUBKMWFYVHYZAI-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- 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
- 229910052980 cadmium sulfide Inorganic materials 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- 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 1
- 235000021240 caseins Nutrition 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- ZXJXZNDDNMQXFV-UHFFFAOYSA-M crystal violet Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1[C+](C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 ZXJXZNDDNMQXFV-UHFFFAOYSA-M 0.000 description 1
- 238000007766 curtain coating Methods 0.000 description 1
- 125000004966 cyanoalkyl group Chemical group 0.000 description 1
- 125000004802 cyanophenyl group Chemical group 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000006534 ethyl amino methyl group Chemical group [H]N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 230000005496 eutectics Effects 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 229910001385 heavy metal Inorganic materials 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
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 229920001600 hydrophobic polymer Polymers 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 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
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- DZVCFNFOPIZQKX-LTHRDKTGSA-M merocyanine Chemical compound [Na+].O=C1N(CCCC)C(=O)N(CCCC)C(=O)C1=C\C=C\C=C/1N(CCCS([O-])(=O)=O)C2=CC=CC=C2O\1 DZVCFNFOPIZQKX-LTHRDKTGSA-M 0.000 description 1
- 239000000113 methacrylic resin Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- DCZNSJVFOQPSRV-UHFFFAOYSA-N n,n-diphenyl-4-[4-(n-phenylanilino)phenyl]aniline Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 DCZNSJVFOQPSRV-UHFFFAOYSA-N 0.000 description 1
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 1
- 210000003739 neck Anatomy 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000004971 nitroalkyl group Chemical group 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229930184652 p-Terphenyl Natural products 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 239000013034 phenoxy resin Substances 0.000 description 1
- 229920006287 phenoxy resin Polymers 0.000 description 1
- 229920002382 photo conductive polymer Polymers 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920002587 poly(1,3-butadiene) polymer Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate 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
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- RCYFOPUXRMOLQM-UHFFFAOYSA-N pyrene-1-carbaldehyde Chemical compound C1=C2C(C=O)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 RCYFOPUXRMOLQM-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 229940043267 rhodamine b Drugs 0.000 description 1
- 238000007761 roller coating Methods 0.000 description 1
- 229930187593 rose bengal Natural products 0.000 description 1
- 229940081623 rose bengal Drugs 0.000 description 1
- STRXNPAVPKGJQR-UHFFFAOYSA-N rose bengal A Natural products O1C(=O)C(C(=CC=C2Cl)Cl)=C2C21C1=CC(I)=C(O)C(I)=C1OC1=C(I)C(O)=C(I)C=C21 STRXNPAVPKGJQR-UHFFFAOYSA-N 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 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
- AUHHYELHRWCWEZ-UHFFFAOYSA-N tetrachlorophthalic anhydride Chemical compound ClC1=C(Cl)C(Cl)=C2C(=O)OC(=O)C2=C1Cl AUHHYELHRWCWEZ-UHFFFAOYSA-N 0.000 description 1
- PCCVSPMFGIFTHU-UHFFFAOYSA-N tetracyanoquinodimethane Chemical compound N#CC(C#N)=C1C=CC(=C(C#N)C#N)C=C1 PCCVSPMFGIFTHU-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 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
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 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
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 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
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Photoreceptors In Electrophotography (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、電子写真用感光体に関し、更に詳しくは、ビ
スメソイオン化合物を含有する感光層を有する電子写真
用感光体に関するものである。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to an electrophotographic photoreceptor, and more particularly to an electrophotographic photoreceptor having a photosensitive layer containing a bismesoion compound.
光導電性物質と静電現象を結び付けて画像記録を行なう
、いわゆる電子写真法は、カールソンが米国特許第22
1776号に於いて明らかにした「エレクトロン フォ
トグラフィ」に端を発している。電子写真法では、光の
照射量に応じてその電気抵抗が変化する光導電物質を、
絶縁性のバインダー樹脂に分散し、これを支持体上に塗
布した光導電性材料が感光体として用いられる。この光
導電材料は、暗所でコロナ帯電により一様な表面電荷を
与えられたのち、画像露光の明るさの値に応じた表面電
荷を失い静電潜像が形成される。この様な静電潜像は、
次にその表面が適当な検電表示物質、すなわちトナーで
処理されて可視像となる。トナーは乾燥担体と共に、或
いは有機溶剤中にコロイド状に懸濁して用いられ、静電
潜像の電荷に応じてクーロン力によって付着させること
ができる。付着した表示物質は、熱、圧力などにより定
着させることができる。So-called electrophotography, which combines photoconductive substances and electrostatic phenomena to record images, was developed by Carlson in U.S. Pat.
It originated from the ``electron photography'' that was revealed in issue 1776. In electrophotography, a photoconductive material whose electrical resistance changes depending on the amount of light irradiation is used.
A photoconductive material that is dispersed in an insulating binder resin and coated on a support is used as a photoreceptor. After this photoconductive material is given a uniform surface charge by corona charging in a dark place, it loses its surface charge depending on the brightness value of image exposure, and an electrostatic latent image is formed. This kind of electrostatic latent image is
The surface is then treated with a suitable electrolytic indicator material, ie, toner, to form a visible image. The toner can be used with a dry carrier or colloidally suspended in an organic solvent and can be deposited by Coulomb force depending on the charge of the electrostatic latent image. The attached display substance can be fixed by heat, pressure, or the like.
また、静電潜像は第2の支持体(例えば、紙、フィルム
等)に転写し、現像、定着させることもできる。The electrostatic latent image can also be transferred to a second support (eg, paper, film, etc.), developed, and fixed.
この様な電子写真法に於いて、電子写真用感光体に要求
される基本的な特性としては、(1)暗所で適当な電位
に帯電できること、(2)暗所における電荷の保持能力
が大きいこと、(3)光照射によって速やかに電荷を散
逸できること、などが挙げられる。In such electrophotography, the basic characteristics required of an electrophotographic photoreceptor are (1) ability to be charged to an appropriate potential in the dark, and (2) ability to retain charge in the dark. and (3) the ability to quickly dissipate charge by light irradiation.
また、実用面からは、(4)適当な面積を持つ感光体が
容易に造れること、(5)繰り返し安定性が良いこと、
(6)耐久性があること、(7)安価なこと、などが要
求されている。In addition, from a practical standpoint, (4) a photoreceptor with an appropriate area can be easily manufactured, (5) it has good repeat stability,
(6) It must be durable, and (7) It must be inexpensive.
従来、電子写真用感光体の光導電性材料としては、セレ
ン、硫化カドミウム、酸化亜鉛などが広く用いられてき
た。しかしながら、これらの無機化合物は、多くの長所
を持つ反面、様々な欠点を有していることも事実である
。例えば、セレンは製造する条件が難しく、製造コスト
が高い、温度、湿度、指紋などにより容易に結晶化が進
み、感光体としての特性が劣化してしまう為に取り扱い
に注意を要するなどの欠点を持っていた。また、硫化カ
ドごラムは、特に耐湿性が悪く、感光体の吸湿を防止す
る為にヒーターを設置するなどの補助手段が必要であっ
た。また、酸化亜鉛は、硬度、耐摩耗性など機械的な強
度に問題がある他、ローズベンガルに代表される染料で
増感しているため、コロナ帯電による染料の光退色が感
光体の寿命を縮めていた。これらの無機化合物は、重金
属を含有し、取扱いを誤まると公害問題に発展する危険
性もあった。Conventionally, selenium, cadmium sulfide, zinc oxide, and the like have been widely used as photoconductive materials for electrophotographic photoreceptors. However, while these inorganic compounds have many advantages, they also have various disadvantages. For example, selenium has drawbacks such as difficult manufacturing conditions, high manufacturing costs, and the need for careful handling as it easily crystallizes due to temperature, humidity, fingerprints, etc., and deteriorates its properties as a photoreceptor. had. Further, sulfurized cadmium has particularly poor moisture resistance, and auxiliary means such as installing a heater are required to prevent the photoreceptor from absorbing moisture. In addition, zinc oxide has problems with mechanical strength such as hardness and abrasion resistance, and since it is sensitized with dyes such as rose bengal, photobleaching of the dye due to corona charging can shorten the life of the photoreceptor. It was shrinking. These inorganic compounds contain heavy metals, and if handled incorrectly, there is a risk of developing a pollution problem.
近年、これらの無機化合物の光導電性材料の欠点を克服
する為に、種々の有機光導電性化合物を用いた電子写真
用感光体の研究開発が盛んに行なわれている。例えば、
ポリ−N−ビニルカルバゾールと2.4.7− )リニ
トロフルオレノンとからなる電子写真用感光体(米国特
許第3.484,237号)、ボIJ N−ビニルカ
ルバゾールをピリリウム塩系色素で増感したもの(特公
昭48−25658号)、染料と樹脂とからなる共晶体
を光導電性材料とするもの(特開昭47−10785号
)などがある。この様な有機化合物系電子写真用感光体
は、無機化合物系電子写真感光体に比べて、成膜が容易
であり、極めて生産性が高く、安価な感光体を提供でき
ると言う利点を持っている。しかしながら、例えば、ポ
リ−N−ビニルカルバゾールの様な光導電性ポリマーに
関しては、ポリマー単独では被膜性、可撓性、接着性な
どが不良であり、これらの欠点を改良する為に可塑材、
バインダーなどが添加されるが、この為に感度の低下や
、残留電位の上昇を招くなどの問題点があった。In recent years, in order to overcome the drawbacks of these inorganic compound photoconductive materials, research and development of electrophotographic photoreceptors using various organic photoconductive compounds has been actively conducted. for example,
Electrophotographic photoreceptor consisting of poly-N-vinylcarbazole and 2.4.7-)linitrofluorenone (U.S. Pat. No. 3,484,237), BoIJ N-vinylcarbazole enhanced with pyrylium salt dye. (Japanese Patent Publication No. 48-25658), and one in which a eutectic consisting of a dye and a resin is used as a photoconductive material (Japanese Patent Application Laid-Open No. 47-10785). Compared to inorganic compound-based electrophotographic photoreceptors, such organic compound-based electrophotographic photoreceptors have the advantage of being easier to form a film, have extremely high productivity, and can provide inexpensive photoreceptors. There is. However, for photoconductive polymers such as poly-N-vinylcarbazole, the polymer alone has poor filmability, flexibility, adhesion, etc., and in order to improve these drawbacks, plasticizers,
A binder or the like is added, but this causes problems such as a decrease in sensitivity and an increase in residual potential.
また、有機化合物系の低分子光導電性化合物は、バイン
ダーの選択範囲も広く、適当なポリマーを選択すれば、
被膜性、接着性など機械的特性の優れたものを造ること
ができるが、反面、光感度、繰り返し特性など電子写真
用感光体としての要求を十分に満たすものではなかった
。In addition, organic compound-based low-molecular photoconductive compounds have a wide range of binders to choose from, and if an appropriate polymer is selected,
Although it is possible to produce products with excellent mechanical properties such as filmability and adhesiveness, on the other hand, they do not fully satisfy the requirements for electrophotographic photoreceptors such as photosensitivity and repeatability.
本発明が解決しようとする課題は、従来の無機化合物系
電子写真用感光体の欠点を克服し、且つこれまで提案さ
れてきた有機化合物系電子写真用感光体の欠点を改良し
、十分に実用に供しうる程度の高感度、高耐久性を有す
る電子写真用感光体を提供することにある。The problem to be solved by the present invention is to overcome the drawbacks of conventional inorganic compound-based electrophotographic photoreceptors, and improve the drawbacks of the organic compound-based electrophotographic photoreceptors that have been proposed so far, so as to be fully practical. The object of the present invention is to provide an electrophotographic photoreceptor having high sensitivity and high durability that can be used for various purposes.
本発明は上記課題を解決するために、
一般式(I)
(式中、Aは置換基を有しても良い芳香族炭化水素基又
は芳香族複素環基の2価の残基を表わし、Rは置換基を
有しても良い炭化水素基又は置換基を有しても良い複素
環基を表わす。)
で表わされる化合物を含有することを特徴とする電子写
真用感光体を提供する。In order to solve the above-mentioned problems, the present invention has the following formula: R represents a hydrocarbon group which may have a substituent or a heterocyclic group which may have a substituent.
一般式(I)におけるAとしては、1.4−フェニレン
基、1,3−フェニレン基、(3,3’−ジメチルビフ
ェニル) −4,4’−ジイル基、(3,3’−ジクロ
ロビフェニル) −4,4’−ジイル基、スチルベン−
4,4′−ジイル基、9−フルオレノン−2,7−ジイ
ル基、2,5−ビフェニルオキサジアゾール−4′、4
“−ジイル基、2−フェニルベンゾオキサゾール−5,
4′−ジイル基などが挙げられる。As A in general formula (I), 1,4-phenylene group, 1,3-phenylene group, (3,3'-dimethylbiphenyl)-4,4'-diyl group, (3,3'-dichlorobiphenyl group) ) -4,4'-diyl group, stilbene-
4,4'-diyl group, 9-fluorenone-2,7-diyl group, 2,5-biphenyloxadiazole-4',4
“-diyl group, 2-phenylbenzoxazole-5,
Examples include 4'-diyl group.
一般式(1)におけるRとしては、例えば、好ましくは
炭素数1〜20のアルキル基、フェニル基、ナフチル基
などの芳香族炭化水素基、ピリジル基、カルバゾリル基
、ベンゾトリアゾリル基などの芳香族複素環基などが挙
げられる。具体例としては、Rがアルキル基の場合は、
メチル基、エチル基、プロピル基、ブチル基、ペンチル
基、ヘキシル基、イソプロピル基、イソブチル基、イソ
ブチル基、イソヘキシル基、ネオペンチル基、ter
t−ブチル基などを挙げることができる。Rが置換アル
キル基の場合は、置換基としては、ハロゲン原子、ニト
ロ基、シアノ基、ヒドロキシ基、置換ヒドロキシ基、チ
オール基、置換チオール基、アミノ基、置換アミノ基、
アリール基などが挙げられる。R in the general formula (1) is preferably an alkyl group having 1 to 20 carbon atoms, an aromatic hydrocarbon group such as a phenyl group or a naphthyl group, or an aromatic group such as a pyridyl group, a carbazolyl group, or a benzotriazolyl group. Examples include group heterocyclic groups. As a specific example, when R is an alkyl group,
Methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, isopropyl group, isobutyl group, isobutyl group, isohexyl group, neopentyl group, ter
Examples include t-butyl group. When R is a substituted alkyl group, examples of the substituent include a halogen atom, a nitro group, a cyano group, a hydroxy group, a substituted hydroxy group, a thiol group, a substituted thiol group, an amino group, a substituted amino group,
Examples include aryl groups.
Rの具体例としては、ハロゲノアルキル基(例えば、ク
ロロメチル基、トリフルオロメチル基、2−ブロモエチ
ル基等)、ニトロアルキル基(例えば、ニトロメチル基
、3−ニトロプロピル基等)シアノアルキル基(例えば
、シアノメチル基、2−シアノエチル基等)、ヒドロキ
シアルキル基(例えば、ヒドロキシメチル基、2−ヒド
ロキシエチル基、3−ヒドロキシプロピル基、2−ヒド
ロキシプロピル基等)、置換ヒドロキシアルキル基(例
えば、メトキシメチル基、2−メトキシエチル基、エト
キシメチル基、フェノキシメチル基等)、チオヒドロキ
シアルキル基(例えば、チオヒドロキシメチル基、2−
チオヒドロキシエチル基等)、置換チオヒドロキシアル
キル基(例えば、メチルチオメチル基、2−メチルチオ
エチル基)、アミノアルキル基(例えば、ア逅ノメチル
基、2−アごノエチル基等)、置換アミノアルキル基(
例えば、メチルアごノメチル基、エチルアミノメチル基
、ジメチルアミノメチル基、2−(ジメチルアミ〕)エ
チル基、フェニルアミノメチル基、ジフェニルアミノメ
チル基等)を挙げることができる。Specific examples of R include halogenoalkyl groups (e.g., chloromethyl group, trifluoromethyl group, 2-bromoethyl group, etc.), nitroalkyl groups (e.g., nitromethyl group, 3-nitropropyl group, etc.), cyanoalkyl groups (e.g., , cyanomethyl group, 2-cyanoethyl group, etc.), hydroxyalkyl group (e.g., hydroxymethyl group, 2-hydroxyethyl group, 3-hydroxypropyl group, 2-hydroxypropyl group, etc.), substituted hydroxyalkyl group (e.g., methoxymethyl group, 2-methoxyethyl group, ethoxymethyl group, phenoxymethyl group, etc.), thiohydroxyalkyl group (e.g., thiohydroxymethyl group, 2-methoxyethyl group, ethoxymethyl group, phenoxymethyl group, etc.),
thiohydroxyethyl group, etc.), substituted thiohydroxyalkyl group (e.g., methylthiomethyl group, 2-methylthioethyl group), aminoalkyl group (e.g., agonomethyl group, 2-agonoethyl group, etc.), substituted aminoalkyl group (
Examples include methylagonomethyl group, ethylaminomethyl group, dimethylaminomethyl group, 2-(dimethylami)ethyl group, phenylaminomethyl group, diphenylaminomethyl group, etc.).
Rが芳香族炭化水素基或いは芳香族複素環基である場合
の置換基としては、アルキル基、ハロゲン原子、ニトロ
基、シアノ基、ヒドロキシ基、置換ヒドロキシ基、チオ
ール基、置換チオール基、アミノ基、置換アミノ基など
がある。具体例としてRが置換フェニル基の場合を挙げ
ると、アルキルフェニル基(例えば、トリル基、エチル
フェニル基等)、クロロフェニル基、ニトロフェニル基
、シアノフェニル基、ヒドロキシフェニル基、置換ヒド
ロキシフェニル基(例えば、メトキシフェニル基、エト
キシフェニル基等)、チオヒドロキシフェニル基、置換
チオール基(例えば、メチルチオナフチル基、エチルチ
オフェニル基等)、アミノフェニル基、置換アミノ基(
例えば、メチルアミノフェニル基、ジメチルアくノフェ
ニル基、フェニルアミノフェニル基、ジメチルアミノメ
チル基等)がある。Rが縮合芳香族炭化水素基の例とし
て、置換ナフチル基の場合を挙げると、アルキルナフチ
ル基(例えば、メチルナフチル基、エチルナフチル基等
)、クロロナフチル基、ニトロナフチル基、シアノナフ
チル基、ヒドロキシナフチル基、置換ヒドロキシナフチ
ル基(例えば、メトキシナフチル基、エトキシナフチル
基等)、チオヒドロキシナフチル基、置換チオール基(
例えば、メチルチオナフチル基、エチルチオナフチル基
等)、アミノナフチル基、置換アミノ基(例えば、メチ
ルアミノナフチル基、ジメチルアミノナフチル基、フェ
ニルアミノナフチル基、ジフェニルアミノナフチル基等
)がある。芳香族複素環基の例として、置換ベンゾチア
ゾリル基の場合を上げると、アルキルベンゾチアゾリル
基(例えば、メチルベンゾチアゾリル基、エチルベンゾ
ベンゾチアゾリル基等)、クロロベンゾチアゾリル基、
ニトロベンゾチアゾリル基、シアノベンゾチアゾリル基
、ヒドロキシベンゾチアゾリル基、置換ヒドロキシベン
ゾチアゾリル基(例えば、メトキシベンゾチアゾリル基
、エトキシベンゾチアゾリル基等)、チオヒドロキシベ
ンゾチアゾリル基、置換チオール基(例えば、メチルチ
オベンゾチアゾリル基、エチルチオベンゾチアゾリル基
等)、アミノベンゾチアゾリル基、置換アミノベンゾチ
アゾリル基(例えば、メチルアミノベンゾチアゾリル基
、ジメチルアミノベンゾチアゾリル基、フェニルアミノ
ベンゾチアゾリル基、ジフェニルアごノナベンゾチアゾ
リル基等)がある。尚、これらの例中置換基の位置の指
定のないものは、可能な異性体のいずれでも良い。また
、これらの置換基(互いに同じでも異なっていても良い
。)を2個以上を有する置換芳香族炭化水素基又は置換
芳香族複素環基であってもよい。When R is an aromatic hydrocarbon group or an aromatic heterocyclic group, examples of the substituent include an alkyl group, a halogen atom, a nitro group, a cyano group, a hydroxy group, a substituted hydroxy group, a thiol group, a substituted thiol group, and an amino group. , substituted amino groups, etc. As a specific example, when R is a substituted phenyl group, an alkylphenyl group (e.g. tolyl group, ethylphenyl group, etc.), a chlorophenyl group, a nitrophenyl group, a cyanophenyl group, a hydroxyphenyl group, a substituted hydroxyphenyl group (e.g. , methoxyphenyl group, ethoxyphenyl group, etc.), thiohydroxyphenyl group, substituted thiol group (e.g., methylthionaphthyl group, ethylthiophenyl group, etc.), aminophenyl group, substituted amino group (
Examples include methylaminophenyl group, dimethylachinophenyl group, phenylaminophenyl group, dimethylaminomethyl group, etc.). Examples of fused aromatic hydrocarbon groups in which R is a substituted naphthyl group include alkylnaphthyl groups (e.g., methylnaphthyl group, ethylnaphthyl group, etc.), chloronaphthyl group, nitronaphthyl group, cyanonaphthyl group, hydroxy Naphthyl group, substituted hydroxynaphthyl group (e.g. methoxynaphthyl group, ethoxynaphthyl group, etc.), thiohydroxynaphthyl group, substituted thiol group (
Examples include methylthionaphthyl group, ethylthionaphthyl group, aminonaphthyl group, and substituted amino groups (eg, methylaminonaphthyl group, dimethylaminonaphthyl group, phenylaminonaphthyl group, diphenylaminonaphthyl group, etc.). Examples of aromatic heterocyclic groups include substituted benzothiazolyl groups, such as alkylbenzothiazolyl groups (e.g., methylbenzothiazolyl group, ethylbenzobenzothiazolyl group, etc.), and chlorobenzothiazolyl groups. ,
Nitrobenzothiazolyl group, cyanobenzothiazolyl group, hydroxybenzothiazolyl group, substituted hydroxybenzothiazolyl group (e.g., methoxybenzothiazolyl group, ethoxybenzothiazolyl group, etc.), thiohydroxybenzo Thiazolyl group, substituted thiol group (e.g., methylthiobenzothiazolyl group, ethylthiobenzothiazolyl group, etc.), aminobenzothiazolyl group, substituted aminobenzothiazolyl group (e.g., methylaminobenzothiazolyl group, etc.) group, dimethylaminobenzothiazolyl group, phenylaminobenzothiazolyl group, diphenylaminobenzothiazolyl group, etc.). In these examples, if the position of the substituent is not specified, any of the possible isomers may be used. Further, it may be a substituted aromatic hydrocarbon group or a substituted aromatic heterocyclic group having two or more of these substituents (which may be the same or different).
本発明に係わる一般式(1)で表わされるビスメソイオ
ン化合物は、従来公知の方法で製造することができる。The bismesoionic compound represented by the general formula (1) according to the present invention can be produced by a conventionally known method.
例えば、「へくツシェ ベリッヒテ」第120巻、41
1頁(1987年)に記載の如く、次のような経路で合
成することができる。For example, "Hekutsche Berichte" Volume 120, 41
1 (1987), it can be synthesized by the following route.
r 0
1
A +CHCOH)2
(CF30) zo
O
本発明で使用される前記−数式(I)のビスメソイオン
化合物の具体例を第1表に構造式で示す。r 0 1 A +CHCOH) 2 (CF30) zo O Specific examples of the bismeso ion compound of formula (I) used in the present invention are shown in Table 1 as structural formulas.
本発明の電子写真用感光体は種々の構造をとることがで
きる。その例を第1〜4図に示した。第1図の感光体は
、導電性支持体(1)上にビスメソイオン化合物(3)
をバインダー(4)中に分散させてなる感光層(2a)
を設けたものである。The electrophotographic photoreceptor of the present invention can have various structures. Examples are shown in Figures 1-4. The photoreceptor in Figure 1 consists of a bismesoionic compound (3) on a conductive support (1).
A photosensitive layer (2a) formed by dispersing in a binder (4)
It has been established.
第2図の感光体は、導電性支持体上にビスメソイオン化
合物(3)を電荷輸送物質(5)及びバインダーから成
る電荷輸送媒体に分散させて戒る感光層(2b)を設け
たものである。第3図及び第4図の感光体はビスメソイ
オン化合物(3)を主体とする電荷担体発生層(6)と
、電荷輸送物質とバインダーから成る電荷輸送層(7)
とから成る感光層(2c)又は(2d)をそれぞれ設け
たものである。第1図の場合には、ビスメソイオン化合
物(3)は、光減衰に必要な電荷担体の発生及び電荷輸
送の両件用を行なっている。第2図の感光体の場合には
、電荷輸送物質はバインダーと共に電荷輸送媒体(5)
を形成し、一方ビスメソイオン化合物(3)は電荷担体
発生物質として作用する。この電荷輸送媒体(5)はビ
スメソイオン化合物(3)の如き電荷担体の生成能力は
持たないが、ビスメソイオン化合物から発生した電荷担
体を受は入れ、これを輸送する能力を持っている。即ち
、第2図の感光体では光減衰に必要な電荷担体の生成は
ビスメソイオン化合物(3)によって行なわれ、一方、
電荷担体の輸送は主として電荷輸送媒体(5)により行
なわれる。第3図及び第4図の感光体の場合には、電荷
担体発生層(6)に含まれるビスメソイオン化合物(3
)は電荷担体を発生し、一方、電荷輸送層(7)は電荷
担体の注入を受けその輸送を行なう。即ち、光減衰に必
要な電荷担体の生成がビスメソイオン化合物で行なわれ
、又、電荷担体の輸送が電荷輸送媒体で行なわれると言
う作用機構は第2図の感光体の場合と同様である。The photoreceptor shown in Fig. 2 has a photosensitive layer (2b) formed by dispersing a bismeso ion compound (3) in a charge transport medium consisting of a charge transport substance (5) and a binder on a conductive support. . The photoreceptor shown in FIGS. 3 and 4 includes a charge carrier generation layer (6) mainly composed of a bismesoionic compound (3), and a charge transport layer (7) composed of a charge transport substance and a binder.
A photosensitive layer (2c) or (2d) consisting of the following is provided. In the case of FIG. 1, the bismesoionic compound (3) performs both the generation of charge carriers necessary for light attenuation and charge transport. In the case of the photoreceptor of FIG. 2, the charge transport material is a charge transport medium (5) along with a binder.
, while the bismesoionic compound (3) acts as a charge carrier generating substance. Although this charge transport medium (5) does not have the ability to generate charge carriers like the bismesoionic compound (3), it has the ability to accept charge carriers generated from the bismesoionic compound and transport them. That is, in the photoreceptor of FIG. 2, the generation of charge carriers necessary for light attenuation is performed by the bismesoionic compound (3), while
Transport of the charge carriers is primarily carried out by the charge transport medium (5). In the case of the photoreceptors shown in FIGS. 3 and 4, the bismeso ion compound (3
) generates charge carriers, while the charge transport layer (7) receives charge carrier injection and transports them. That is, the mechanism of action is the same as that of the photoreceptor shown in FIG. 2, in which the generation of charge carriers necessary for light attenuation is carried out by a bismeso ion compound, and the transport of charge carriers is carried out by a charge transport medium.
第1図の感光体はビスメソイオン化合物をバインダー溶
液中に分散させ、この分散液を導電性支持体上に塗布、
乾燥することによって製造することができる。第2図の
感光体はビスメソイオン化合物を電荷輸送物質及びバイ
ンダーを溶解した溶液中に分散せしめ、この分散液を導
電性支持体上に塗布、乾燥することによって製造するこ
とができる。また、第3図の感光体は、導電性支持体上
にビスメソイオン化合物を真空蒸着するか、或いは、ビ
スメソイオン化合物の微粒子を溶剤又はバインダー溶液
中に分散して得た分散液を塗布、乾燥し、その上に電荷
輸送物質及びバインダーを溶解した溶液を塗布、乾燥す
ることにより製造することができる。第4図の感光体は
電荷輸送物質及びバインダーを溶解した溶液を導電性支
持体上に塗布、乾燥し、その上にビスメソイオン化合物
を真空蒸着するか、或いはビスメソイオン化合物の微粒
子を溶剤又はバインダー溶液中に分散して得た分散液を
塗布、乾燥することにより製造することができる。The photoreceptor shown in FIG. 1 is made by dispersing a bismeso ion compound in a binder solution, coating this dispersion on a conductive support,
It can be manufactured by drying. The photoreceptor shown in FIG. 2 can be manufactured by dispersing a bismeso ion compound in a solution containing a charge transporting substance and a binder, coating this dispersion on a conductive support, and drying it. The photoreceptor shown in FIG. 3 can be obtained by vacuum-depositing a bismesoionic compound on a conductive support, or by applying a dispersion obtained by dispersing fine particles of a bismesoionic compound in a solvent or binder solution, and drying the resulting material. It can be manufactured by applying a solution containing a charge transporting substance and a binder thereon and drying it. The photoreceptor shown in Fig. 4 is produced by coating a conductive support with a solution containing a charge transport substance and a binder and drying it, and then vacuum-depositing a bismesoion compound thereon, or by depositing fine particles of a bismesoion compound in a solvent or binder solution. It can be manufactured by applying and drying a dispersion obtained by dispersing the liquid into a liquid.
これらの感光体の感光層の厚さは、第1図及び第2図の
感光体の場合、3〜50am、好ましくは5〜20μm
である。又第3図及び第4図の感光体の場合には、電荷
担体発生層の厚さは5μm以下、好ましくは0.01〜
2μmであり、電荷輸送層の厚さは3〜50μm、好ま
しくは5〜20μmである。又、第1図の感光体に於い
て、感光層中のビスメソイオン化合物の割合は、感光層
に対して10〜70重量%、好ましくは30〜50重量
%である。第2図の感光体に於いては、感光層中のビス
メソイオン化合物の割合は1〜50重量%、好ましくは
3〜30重量%であり、又、電荷輸送物質の割合は10
〜90重量%、好ましくは10〜60重量%である。第
3図及び第4図の感光体における電荷輸送媒体中の電荷
輸送物質の割合は10〜95重量%、好ましくは10〜
60重量%である。The thickness of the photosensitive layer of these photoreceptors is 3 to 50 am, preferably 5 to 20 μm in the case of the photoreceptors shown in FIGS. 1 and 2.
It is. In the case of the photoreceptor shown in FIGS. 3 and 4, the thickness of the charge carrier generation layer is 5 μm or less, preferably 0.01 to 5 μm.
2 μm, and the thickness of the charge transport layer is 3 to 50 μm, preferably 5 to 20 μm. In the photoreceptor shown in FIG. 1, the proportion of the bismeso ion compound in the photosensitive layer is 10 to 70% by weight, preferably 30 to 50% by weight, based on the photosensitive layer. In the photoreceptor shown in FIG. 2, the proportion of the bismeso ion compound in the photosensitive layer is 1 to 50% by weight, preferably 3 to 30% by weight, and the proportion of the charge transport substance is 10% by weight.
-90% by weight, preferably 10-60% by weight. The proportion of the charge transport material in the charge transport medium in the photoreceptor of FIGS. 3 and 4 is 10 to 95% by weight, preferably 10 to 95% by weight.
It is 60% by weight.
本発明の感光体に用いられる導電性支持体としては、例
えば、アルミニウム、銅、亜鉛、ステンレス、クロム、
チタン、ニッケル、モリブデン、バナジウム、インジウ
ム、金、白金等の金属または合金を用いた金属板、金属
ドラム、或いは、導電性ポリマー、酸化インジウム等の
導電性化合物やアルごニウム、パラジウム、金等の金属
又は合金を塗布、蒸着、或いはう果ネートした紙、プラ
スチックフィルム等が挙げられる。Examples of the conductive support used in the photoreceptor of the present invention include aluminum, copper, zinc, stainless steel, chromium,
Metal plates and metal drums made of metals or alloys such as titanium, nickel, molybdenum, vanadium, indium, gold, and platinum, or conductive polymers, conductive compounds such as indium oxide, argonium, palladium, gold, etc. Examples include paper, plastic film, etc. coated with, vapor-deposited, or plated with metals or alloys.
バインダーとしては、疎水性で、電気絶縁性のフィルム
形成可能な高分子重合体を用いるのが好ましい。この様
な高分子重合体としては、例えば、ポリカーボネート、
ポリエステル、メタクリル樹脂、アクリル樹脂、ポリ塩
化ビニル、ポリ塩化ビニリデン、ポリスチレン、ポリビ
ニルアセテート、スチレン−ブタジェン共重合体、塩化
ビニリデン−アクリロニトリル共重合体、塩化ビニル−
酢酸ビニル共重合体、塩化ビニル−酢酸ビニル−無水マ
レイン酸共重合体、シリコン樹脂、シリコン−アルキッ
ド樹脂、フェノール−ホルムアルデヒド樹脂、スチレン
−アルキッド樹脂、ポリ−N−ビニルカルバゾール、ポ
リビニルブチラール、ポリビニルフォルマール、ポリス
ルホン等が挙げられるが、これらに限定されるものでは
ない。As the binder, it is preferable to use a hydrophobic polymer capable of forming an electrically insulating film. Examples of such high molecular weight polymers include polycarbonate,
Polyester, methacrylic resin, acrylic resin, polyvinyl chloride, polyvinylidene chloride, polystyrene, polyvinyl acetate, styrene-butadiene copolymer, vinylidene chloride-acrylonitrile copolymer, vinyl chloride
Vinyl acetate copolymer, vinyl chloride-vinyl acetate-maleic anhydride copolymer, silicone resin, silicone-alkyd resin, phenol-formaldehyde resin, styrene-alkyd resin, poly-N-vinylcarbazole, polyvinyl butyral, polyvinyl formal , polysulfone, etc., but are not limited to these.
これらの結着剤は、単独で、或いは2種類以上の混合物
として用いることもできる。These binders can be used alone or as a mixture of two or more.
又、これらのバインダーと共に、可塑剤、増感剤、表面
改質剤等の添加剤を使用することもてきる。Additionally, additives such as plasticizers, sensitizers, surface modifiers, etc. can also be used together with these binders.
可塑剤としては、例えば、ビフェニル、塩化ビフェニル
、0−ターフエル、p−ターフェニル、ジブチルフタレ
ート、ジエチレングリコールフタレート、ジオクチルフ
タレート、トリフェニル燐酸、メチルナフタレン、ベン
ゾフェノン塩素化パラフィン、ポリプロピレン、ポリス
チレン、各種フルオロ炭化水素等が挙げられる。Examples of plasticizers include biphenyl, chlorinated biphenyl, 0-terphel, p-terphenyl, dibutyl phthalate, diethylene glycol phthalate, dioctyl phthalate, triphenyl phosphoric acid, methylnaphthalene, benzophenone, chlorinated paraffin, polypropylene, polystyrene, and various fluorohydrocarbons. etc.
増感剤としては、例えばクロラニル、テトラシアノエチ
レン、メチルバイオレット、ローダミンB、シアニン染
料、メロシアニン染料、ピリリウム染料、チアピリリウ
ム染料等が挙げられる。Examples of the sensitizer include chloranil, tetracyanoethylene, methyl violet, rhodamine B, cyanine dye, merocyanine dye, pyrylium dye, and thiapyrylium dye.
表面改質剤としては、例えばシリコンオイル、フッソ樹
脂等が挙げられる。Examples of the surface modifier include silicone oil and fluorine resin.
更に本発明に於いては、導電性支持体と感光層との接着
性を向上させたり、導電性支持体から感光層への自由電
荷の注入を阻止する為、導電性支持体と感光層の間に、
必要に応じて接着層或いはバリヤー層を設けることもで
きる。これらの層に用いられる材料としては、前記バイ
ンダーに用いられる高分子化合物のほか、カゼイン、ゼ
ラチン、ポリビニルアルコール、エチルセルロース、ニ
トロセルロース、ポリビニルブチラール、フェノール樹
脂、ポリアミド、カルボキシルメチルセルロース塩化ビ
ニリデン系ポリマーラテックス、スチレン−ブタジェン
系ポリマーラテックス、ポリウレタン、ゼラチン、酸化
アルミニウム、酸化スズ、酸化チタン等が挙げられる。Furthermore, in the present invention, in order to improve the adhesion between the conductive support and the photosensitive layer and to prevent the injection of free charges from the conductive support to the photosensitive layer, Between,
An adhesive layer or barrier layer can also be provided as required. Materials used for these layers include, in addition to the polymer compounds used in the binder, casein, gelatin, polyvinyl alcohol, ethyl cellulose, nitrocellulose, polyvinyl butyral, phenolic resin, polyamide, carboxymethyl cellulose, vinylidene chloride polymer latex, and styrene. -Butadiene polymer latex, polyurethane, gelatin, aluminum oxide, tin oxide, titanium oxide and the like.
又、電荷輸送物質としては、−Cに電子を輸送する化合
物と正孔を輸送する化合物との二種類に分類されるが、
本発明の電子写真用感光体には両者とも使用することが
できる。In addition, charge transport substances are classified into two types: compounds that transport electrons to -C and compounds that transport holes.
Both can be used in the electrophotographic photoreceptor of the present invention.
電子輸送物質としては、例えば、クロラニル、フロモア
ニル、テトラシアノエチレン、テトラシアノキノジメタ
ン、2,4.7−トリニトロ−9−フルオレノン、2,
4,5.7−テトラニトロ−9−フルオレノン、9−ジ
シアノメチレン−2,4,7−)リニトロフルオレノン
、9−ジシアノメチレン−2゜4.5.7−テトラニト
ロフルオレノン、2,4,5.7テトラニトロキサント
ン、2,4.8− )リニトロチオキサントン、テトラ
ニトロカルバゾールクロラニル、2,3−ジクロロ−5
,6−ジジアノベンゾキノン、2,4.7− )ジニト
ロ−9,10−フエナントレンキノン、テトラクロロ無
水フタール酸等を挙げることができる。Examples of electron transport substances include chloranil, furoanil, tetracyanoethylene, tetracyanoquinodimethane, 2,4.7-trinitro-9-fluorenone, 2,
4,5.7-tetranitro-9-fluorenone, 9-dicyanomethylene-2,4,7-)linitrofluorenone, 9-dicyanomethylene-2゜4.5.7-tetranitrofluorenone, 2,4,5 .7 Tetranitroxanthone, 2,4.8-)linitrothioxanthone, Tetranitrocarbazole chloranil, 2,3-dichloro-5
, 6-didianobenzoquinone, 2,4.7-)dinitro-9,10-phenanthrenequinone, and tetrachlorophthalic anhydride.
正孔輸送物質としては、低分子化合物では、例えばピレ
ン、N−エチルカルバゾール、N−イソプロピルカルバ
ゾール、N−フェニルカルバゾール、或いは、N−メチ
ル−2−フェニルヒドラジノ−3−メチリデン−9−エ
チルカルバゾール、N、N−ジフェニルヒドラジノ−3
−メチリデン−9−エチルカルバゾール、p−N、N−
ジメチルアミノベンズアルデヒドジフェニルヒドラゾン
、pN、N−ジエチルアミノベンズアルデヒドジフェニ
ルヒドラゾン、p−N、N−ジフェニルアミノベンズア
ルデヒドジフェニルヒドラゾン等のヒドラゾン類、2.
5−ビス(p−ジエチルアミノフェニル) −1,3,
4−オキサジアゾール、1−フェニル−3−(p−ジエ
チルアミノスチリル)−5(p−ジエチルアミノフェニ
ル)ピラゾリン等のピラゾリン類、トリフェニルアミン
、N、N、N’ 、N’−テトラフェニル−1,1′−
ビフェニル−4,4′ジアミン、N、N’−ジフェニル
−N、N’ −ビス(3−メチルフェニル) −1,1
’−ビフェニル−4,4′−ジアミン等が挙げられる。Examples of the hole transport substance include low molecular weight compounds such as pyrene, N-ethylcarbazole, N-isopropylcarbazole, N-phenylcarbazole, or N-methyl-2-phenylhydrazino-3-methylidene-9-ethylcarbazole. , N,N-diphenylhydrazino-3
-Methylidene-9-ethylcarbazole, p-N, N-
Hydrazones such as dimethylaminobenzaldehyde diphenylhydrazone, pN,N-diethylaminobenzaldehyde diphenylhydrazone, p-N,N-diphenylaminobenzaldehyde diphenylhydrazone,2.
5-bis(p-diethylaminophenyl) -1,3,
4-oxadiazole, pyrazolines such as 1-phenyl-3-(p-diethylaminostyryl)-5(p-diethylaminophenyl)pyrazoline, triphenylamine, N, N, N', N'-tetraphenyl-1 ,1'-
Biphenyl-4,4'diamine, N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1
'-biphenyl-4,4'-diamine and the like.
又、高分子化合物としては、例えばポリ−N−ビニルカ
ルバゾール、ハロゲン化ポリ−N−ビニルカルバゾール
、ポリビニルピレン、ポリビニルアンスラセン、ポリビ
ニルアクリジン、ピレン−ホルムアルデヒド樹脂、エチ
ルカルバゾール−ホルムアルデヒド樹脂、トリフェニル
メタンポリマー等が挙げられる。Examples of polymer compounds include poly-N-vinylcarbazole, halogenated poly-N-vinylcarbazole, polyvinylpyrene, polyvinylanthracene, polyvinylacridine, pyrene-formaldehyde resin, ethylcarbazole-formaldehyde resin, and triphenylmethane polymer. etc.
電荷輸送物質は、ここに記載したものに限定されるもの
ではなく、その使用に際しては単独、或いは2種類以上
混合して用いることができる。The charge transport materials are not limited to those described here, and can be used alone or in combination of two or more kinds.
積層型感光体を塗工によって形成する場合、バインダー
を溶解する溶剤は、バインダーの種類によって異なるが
、下層を溶解しないものの中から選択することが好まし
い。具体的な有機溶剤の例としては、例えば、メタノー
ル、エタノール、nプロパノール等のアルコール頬;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、N、N−ジメチルホルムアミド、N、N−ジメ
チルアセトアミド等のアミド類;テトラヒドロフラン、
ジオキサン、メチルセロソルブ等のエーテル頚;酢酸メ
チル、酢酸エチル等のエステル類;ジメチルスルホキシ
ド、スルホラン等のスルホキシド及びスルホン類;塩化
メチレン、クロロホルム、四塩化炭素、トリクロロエタ
ン等の脂肪族ハロゲン化炭化水素;ベンゼン、トルエン
、キシレン、モノクロルベンゼン、ジクロルベンゼン等
の芳香族類などが挙げられる。When forming a laminated photoreceptor by coating, the solvent that dissolves the binder varies depending on the type of binder, but is preferably selected from those that do not dissolve the lower layer. Specific examples of organic solvents include alcohols such as methanol, ethanol, and n-propanol; ketones such as acetone, methyl ethyl ketone, and cyclohexanone; and amides such as N,N-dimethylformamide and N,N-dimethylacetamide. ;Tetrahydrofuran,
Ether necks such as dioxane and methyl cellosolve; Esters such as methyl acetate and ethyl acetate; Sulfoxides and sulfones such as dimethyl sulfoxide and sulfolane; Aliphatic halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, and trichloroethane; Benzene , toluene, xylene, monochlorobenzene, dichlorobenzene, and other aromatic compounds.
塗工法としては、例えば浸漬コーティング法、スプレー
コーティング法、スピンナーコーティング法、ビードコ
ーティング法、ワイヤーバーコーティング法、ブレード
コーティング法、ローラーコーティング法、カーテンコ
ーティング法等のコーティング法を用いることができる
。As the coating method, coating methods such as dip coating, spray coating, spinner coating, bead coating, wire bar coating, blade coating, roller coating, and curtain coating can be used.
以下、実施例により本発明を具体的に説明するが、これ
により本発明が実施例に限定されるものではない。尚、
実施例中「部」とあるのは「重量部」を示す。又、ビス
メソイオン化合物のNoは第1表中のNo、を意味する
。EXAMPLES Hereinafter, the present invention will be specifically explained with reference to Examples, but the present invention is not limited to the Examples. still,
In the examples, "parts" indicate "parts by weight." Further, No. of the bismeso ion compound means No. in Table 1.
実施例1
ポリエステル樹脂(商品名「バイロン200」東洋紡社
製)10部、No、 1のビスメソイオン化合物10部
及びテトラヒドロフラン80部を振動ミル中で粉砕混合
し、得られた分散液をアルミニウム蒸着したポリエステ
ルフィルム上にワイヤーバーで塗布、乾燥し厚さ約10
μの感光層を持った第1図の構造の感光体を得た。次に
この感光体の感光層面に静電複写紙試験装置Model
5P−428(川口電機製作所社製)を用いて、まず
感光体を暗所で印加電圧−6kVのコロナ放電により帯
電させ、10秒間暗所に放置し、ついでタングステンラ
ンプから、その表面が照度5ルツクスになるように感光
層に光照射を行ない、その表面電位が暗所に10秒間放
置後の表面電位の172に減少する迄の時間を測定し、
感光度El/□(ルックス・秒)を求めたところ、E
1/z= 20.5ルツクス・秒であった。Example 1 10 parts of polyester resin (trade name "Vylon 200" manufactured by Toyobo Co., Ltd.), 10 parts of bismesoionic compound No. 1, and 80 parts of tetrahydrofuran were pulverized and mixed in a vibrating mill, and the resulting dispersion was mixed to form a polyester coated with aluminum. Apply onto the film with a wire bar and dry to a thickness of about 10
A photoreceptor having the structure shown in FIG. 1 having a photoreceptor layer of .mu. was obtained. Next, an electrostatic copying paper tester Model was placed on the photosensitive layer surface of this photoreceptor.
Using 5P-428 (manufactured by Kawaguchi Electric Seisakusho Co., Ltd.), the photoreceptor was first charged in the dark by corona discharge with an applied voltage of -6 kV, left in the dark for 10 seconds, and then the surface was illuminated with an illuminance of 5 by a tungsten lamp. irradiate the photosensitive layer with light such that the photosensitive layer becomes lux, and measure the time until the surface potential decreases to 172, which is the surface potential after leaving it in a dark place for 10 seconds,
When the photosensitivity El/□ (lux/sec) was calculated, E
1/z=20.5 lux·sec.
実施例2
ポリエステル樹脂(実施例1と同製品)3部、2.4.
7− )リニトロー9−フルオレノン3部、No。Example 2 3 parts of polyester resin (same product as Example 1), 2.4.
7-) Rinitro 9-fluorenone 3 parts, no.
1のビスメソイオン化合物0.6部及びテトラヒドロフ
ラン30部をボールミル中で粉砕混合し、得られた分散
液をアルミニウムを蒸着したポリエステルフィルム上に
ワイヤーバーを用いて塗布乾燥し厚さ約9μの感光層を
もった第2図の構造の感光体を作製した。次にこの感光
体の感度を実施例1に準じて測定したところE、/2=
4.0ルツクス・秒であった。0.6 parts of the bismesoionic compound No. 1 and 30 parts of tetrahydrofuran were pulverized and mixed in a ball mill, and the resulting dispersion was applied onto a polyester film coated with aluminum using a wire bar and dried to form a photosensitive layer with a thickness of about 9 μm. A photoreceptor having the structure shown in FIG. 2 was prepared. Next, the sensitivity of this photoreceptor was measured according to Example 1, and E, /2=
It was 4.0 lux·sec.
実施例3
NOllのビスメソイオン化合物3部をフェノキシ樹脂
(商品名r PKHHJユニオンカーバイ1社製)1部
をジオキサン75部に溶解させた液中で振動ミルを用い
て粉砕混合し、得られた分散液をアルミニウム蒸着ポリ
エステルフィルム上にワイヤーバーを用いて塗布乾燥し
、厚さ1μの電荷発生層を形成させた。この電荷発生層
の上にp−ジエチルアミノベンズアルデヒド−ジフェニ
ルヒドラゾン5部、ポリカーボネート樹脂(商品名「パ
ンライトL −1250W J帝人化或社製)5部を塩
化メチレン65部に溶かした溶液をワイヤーバーを用い
て塗布乾燥し厚さ10μの電荷輸送層を形成せしめ第3
図の構造の感光体を得た。こうして作製した感光体の感
度を実施例1に準じて測定したところE I/2= 3
.5ルツクス・秒であった。Example 3 3 parts of NOll bismethionic compound were pulverized and mixed using a vibrating mill in a solution in which 1 part of phenoxy resin (product name: PKHHJ, manufactured by Union Carby Company 1) was dissolved in 75 parts of dioxane, and the resulting dispersion was mixed. The solution was applied onto an aluminum vapor-deposited polyester film using a wire bar and dried to form a charge generation layer with a thickness of 1 μm. A solution of 5 parts of p-diethylaminobenzaldehyde-diphenylhydrazone and 5 parts of polycarbonate resin (trade name: "Panlite L-1250W, manufactured by J Teijin Kaoru Co., Ltd.") dissolved in 65 parts of methylene chloride was placed on top of this charge generation layer using a wire bar. A charge transport layer having a thickness of 10 μm was formed by coating and drying using
A photoreceptor having the structure shown in the figure was obtained. When the sensitivity of the photoreceptor thus prepared was measured according to Example 1, E I/2 = 3.
.. It was 5 lux·sec.
実施例4〜2O
Nα1のビスメソイオン化合物の代りに下記第2表のビ
スメソイオン化合物を夫々用いた以外は実施例3と同じ
方法で第3図の構造の感光体を作成し、実施例1に準じ
て感度の測定を行ない第2表に掲げる結果を得た。Examples 4 to 2O A photoreceptor having the structure shown in FIG. 3 was prepared in the same manner as in Example 3, except that the bismeso ion compounds shown in Table 2 below were used in place of the Nα1 bismeso ion compound, and the photoreceptor was prepared according to Example 1. The sensitivity was measured and the results listed in Table 2 were obtained.
第
表
/
実施例21
電荷輸送物質としてp−ジエチルアミノベンズアルデヒ
ド−ジフェニルヒドラゾンの代りにN−エチルカルバゾ
ール−3−メチリデン−N−アミノインドリンを用いた
以外は実施例3と同じ方法で第3図の構造の感光体を作
威し、実施例1に準じてその感度を測定したところEl
/□=3.2ル・ンクス・秒であった。Table/Example 21 The structure shown in Figure 3 was prepared in the same manner as in Example 3 except that N-ethylcarbazole-3-methylidene-N-aminoindoline was used instead of p-diethylaminobenzaldehyde-diphenylhydrazone as the charge transport material. When a photoreceptor was prepared and its sensitivity was measured according to Example 1, El
/□=3.2 lux seconds.
実施例22〜4O
Nα1のビスメソイオン化合物の代りに下記第3表のジ
スアゾ化合物を夫々用い、且つ電荷輸送物質としてp−
ジエチルア湾ノベンズアルデヒドージフェニルヒドラゾ
ンの代りにN−エチルカルバゾール−3−メチリデン−
N−ア【ノインドリンを用いた以外は実施例3と同じ方
法で第3図の構造の感光体を作成し、実施例1に準じて
感度の測定を行ない第3表に掲げる結果を得た。Examples 22 to 4O Disazo compounds shown in Table 3 below were used in place of the bismeso ion compound of Nα1, and p-
N-Ethylcarbazole-3-methylidene-instead of Diethylua Bay nobenzaldehyde diphenylhydrazone
A photoreceptor having the structure shown in FIG. 3 was prepared in the same manner as in Example 3 except that N-A[noindoline was used. The sensitivity was measured in accordance with Example 1, and the results listed in Table 3 were obtained.
実施例41
電荷輸送物質としてp−ジエチルアミノベンズアルデヒ
ド−ジフェニルヒドラゾンの代りにN−エチルカルバゾ
ール−3−メチリデン−N−アミノテトラヒドロキノリ
ンを用いた以外は実施例3と同じ方法で第3図の構造の
感光体を作威し、実施例1に準じて感度を測定したとこ
ろEl/□=3.6ルツクス・秒であった。Example 41 The structure shown in FIG. 3 was photosensitized in the same manner as in Example 3, except that N-ethylcarbazole-3-methylidene-N-aminotetrahydroquinoline was used instead of p-diethylaminobenzaldehyde-diphenylhydrazone as the charge transport material. When the sensitivity was measured in accordance with Example 1, El/□=3.6 lux·sec.
実施例42〜6O
Nα1のビスメソイオン化合物の代りに下記第4表のビ
スメソイオン化合物を夫々用い、且つ電荷輸送物質とし
てp−ジエチルアミノベンズアルデヒド−ジフェニルヒ
ドラゾンの代りにN−エチルカルバゾール−3−メチリ
デン−N−アミノテトラヒドロキノリンを用いた以外は
実施例3と同じ方法で第3図の構造の感光体を作威し、
実施例1に準じて感度の測定を行ない、第4表に掲げる
結果を得た。Examples 42 to 6O The bismeso ion compounds shown in Table 4 below were used in place of the bismeso ion compound of Nα1, and N-ethylcarbazole-3-methylidene-N-amino was used instead of p-diethylaminobenzaldehyde-diphenylhydrazone as the charge transport substance. A photoreceptor having the structure shown in FIG. 3 was produced in the same manner as in Example 3 except that tetrahydroquinoline was used.
Sensitivity was measured according to Example 1, and the results listed in Table 4 were obtained.
実施例61
ポリカーボネート樹脂(実施例3と同製品)3部、p−
ジエチルア旦ノベンズアルデヒドージフェニルヒドラゾ
ン3部をテトラヒドロフラン35部に溶、かした溶液を
アルミニウムを蒸着したポリエステルフィルム上にワイ
ヤーバーを用いて塗布乾燥し厚さ約10μの電荷輸送層
を形成せしめた。Example 61 3 parts of polycarbonate resin (same product as Example 3), p-
A solution prepared by dissolving 3 parts of diethylaminobenzaldehyde diphenylhydrazone in 35 parts of tetrahydrofuran was applied onto an aluminum-deposited polyester film using a wire bar and dried to form a charge transport layer with a thickness of about 10 μm.
次に実施例3において電荷発生層の形成に用いた塗料を
上記電荷輸送層の上にワイヤーバーを用いて塗布乾燥し
厚さ約0.8μの電荷発生層を形成せしめ第4図の構造
の感光体を得た。こうして作製した感光体の感度を印加
電圧+6kVのコロナ放電を行ない実施例1に準じて測
定したところEl/□−3,フルックス・秒であった。Next, the paint used to form the charge generation layer in Example 3 was applied onto the charge transport layer using a wire bar and dried to form a charge generation layer with a thickness of about 0.8 μm. A photoreceptor was obtained. The sensitivity of the thus produced photoreceptor was measured according to Example 1 by performing corona discharge at an applied voltage of +6 kV, and found to be El/□-3, flux seconds.
本発明の電子写真用感光体は、耐久性に優れ、高感度で
あるので、rpc複写機等に広く利用することができる
。Since the electrophotographic photoreceptor of the present invention has excellent durability and high sensitivity, it can be widely used in RPC copying machines and the like.
第1〜4図は、本発明に係わる電子写真用感光体の拡大
部分断面図である。
1・・・導電性支持体、2a、2b、2c、2d−感光
層、3・・・ビスメソイオン化合物、4・・・バインダ
ー、5・・・電荷輸送物質、6・・・電荷担体発生層、
7・・・電荷輸送層。1 to 4 are enlarged partial cross-sectional views of the electrophotographic photoreceptor according to the present invention. DESCRIPTION OF SYMBOLS 1... Conductive support, 2a, 2b, 2c, 2d-photosensitive layer, 3... Bismeso ion compound, 4... Binder, 5... Charge transport material, 6... Charge carrier generation layer,
7... Charge transport layer.
Claims (1)
は芳香族複素環基の2価の残基を表わし、Rは置換基を
有しても良い炭化水素基又は置換基を有しても良い複素
環基を表わす。) で表わ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。[Claims] 1. General formula (I) ▲ Numerical formula, chemical formula, table, etc. ▼ (In the formula, A is an aromatic hydrocarbon group or an aromatic heterocyclic group which may have a substituent. R represents a hydrocarbon group which may have a substituent or a heterocyclic group which may have a substituent). Photoreceptor for use.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP20395089A JPH0368952A (en) | 1989-08-08 | 1989-08-08 | Electrophotographic sensitive body |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP20395089A JPH0368952A (en) | 1989-08-08 | 1989-08-08 | Electrophotographic sensitive body |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH0368952A true JPH0368952A (en) | 1991-03-25 |
Family
ID=16482358
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP20395089A Pending JPH0368952A (en) | 1989-08-08 | 1989-08-08 | Electrophotographic sensitive body |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH0368952A (en) |
-
1989
- 1989-08-08 JP JP20395089A patent/JPH0368952A/en active Pending
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