JPS62280851A - Organic photoconductor and electrophotographic sensitive body using said photoconductor - Google Patents
Organic photoconductor and electrophotographic sensitive body using said photoconductorInfo
- Publication number
- JPS62280851A JPS62280851A JP12685486A JP12685486A JPS62280851A JP S62280851 A JPS62280851 A JP S62280851A JP 12685486 A JP12685486 A JP 12685486A JP 12685486 A JP12685486 A JP 12685486A JP S62280851 A JPS62280851 A JP S62280851A
- Authority
- JP
- Japan
- Prior art keywords
- photoconductor
- group
- layer
- groups
- charge
- 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
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- 108091008695 photoreceptors Proteins 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 239000000126 substance Substances 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000003277 amino group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 239000000049 pigment Substances 0.000 abstract description 22
- 239000002800 charge carrier Substances 0.000 abstract description 10
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 abstract description 10
- 239000000463 material Substances 0.000 abstract description 10
- 230000035945 sensitivity Effects 0.000 abstract description 5
- 239000003513 alkali Substances 0.000 abstract description 4
- 150000004985 diamines Chemical class 0.000 abstract description 3
- 239000002585 base Substances 0.000 abstract 1
- 230000008878 coupling Effects 0.000 abstract 1
- 238000010168 coupling process Methods 0.000 abstract 1
- 238000005859 coupling reaction Methods 0.000 abstract 1
- 230000003252 repetitive effect Effects 0.000 abstract 1
- 230000032258 transport Effects 0.000 description 34
- -1 multi-ring group Chemical group 0.000 description 17
- 239000000243 solution Substances 0.000 description 16
- 125000001424 substituent group Chemical group 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 238000000576 coating method Methods 0.000 description 12
- 239000010408 film Substances 0.000 description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 11
- 229920005989 resin Polymers 0.000 description 11
- 239000011347 resin Substances 0.000 description 11
- 239000011248 coating agent Substances 0.000 description 10
- 238000001035 drying Methods 0.000 description 10
- 125000001624 naphthyl group Chemical group 0.000 description 10
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 210000003127 knee Anatomy 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- 229910052782 aluminium Inorganic materials 0.000 description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000011230 binding agent Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000005018 casein Substances 0.000 description 5
- 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 5
- 235000021240 caseins Nutrition 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000004372 Polyvinyl alcohol Substances 0.000 description 4
- 229920002451 polyvinyl alcohol Polymers 0.000 description 4
- 125000004076 pyridyl group Chemical group 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 229920000178 Acrylic resin Polymers 0.000 description 3
- 239000004925 Acrylic resin Substances 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 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 3
- 239000006185 dispersion Substances 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 3
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 3
- 229920001230 polyarylate Polymers 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- WUPHOULIZUERAE-UHFFFAOYSA-N 3-(oxolan-2-yl)propanoic acid Chemical compound OC(=O)CCC1CCCO1 WUPHOULIZUERAE-UHFFFAOYSA-N 0.000 description 2
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical group C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 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
- 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
- 239000004677 Nylon Substances 0.000 description 2
- YNORLUXFWIYTRW-UHFFFAOYSA-N Pigment G1 Natural products CCC1(O)CC(OC2CC(C(OC3CC(O)C(OC4CCC(=O)C(C)O4)C(C)O3)C(C)O2)N(C)C)c5cc6C(=O)c7c(O)cccc7C(=O)c6cc5C1C(=O)OC YNORLUXFWIYTRW-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 2
- 125000004103 aminoalkyl group Chemical group 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052980 cadmium sulfide Inorganic materials 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 125000004966 cyanoalkyl group Chemical group 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([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
- 230000005525 hole transport Effects 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 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
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229920001778 nylon Polymers 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920002401 polyacrylamide Polymers 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920000642 polymer Polymers 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
- 125000005493 quinolyl group Chemical group 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- 229910052711 selenium Inorganic materials 0.000 description 2
- 239000011669 selenium Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical group CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical group ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- LFKNYYQRWMMFSM-UHFFFAOYSA-N 1-ethyl-9h-carbazole;formaldehyde Chemical compound O=C.N1C2=CC=CC=C2C2=C1C(CC)=CC=C2 LFKNYYQRWMMFSM-UHFFFAOYSA-N 0.000 description 1
- MYKQKWIPLZEVOW-UHFFFAOYSA-N 11h-benzo[a]carbazole Chemical group C1=CC2=CC=CC=C2C2=C1C1=CC=CC=C1N2 MYKQKWIPLZEVOW-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical group C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-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
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- BWCDLEQTELFBAW-UHFFFAOYSA-N 3h-dioxazole Chemical compound N1OOC=C1 BWCDLEQTELFBAW-UHFFFAOYSA-N 0.000 description 1
- UNTNRNUQVKDIPV-UHFFFAOYSA-N 3h-dithiazole Chemical group N1SSC=C1 UNTNRNUQVKDIPV-UHFFFAOYSA-N 0.000 description 1
- LLLVZDVNHNWSDS-UHFFFAOYSA-N 4-methylidene-3,5-dioxabicyclo[5.2.2]undeca-1(9),7,10-triene-2,6-dione Chemical compound C1(C2=CC=C(C(=O)OC(=C)O1)C=C2)=O LLLVZDVNHNWSDS-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
- 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
- 229930185605 Bisphenol Natural products 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- 229920000305 Nylon 6,10 Polymers 0.000 description 1
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- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- AZWHFTKIBIQKCA-UHFFFAOYSA-N [Sn+2]=O.[O-2].[In+3] Chemical compound [Sn+2]=O.[O-2].[In+3] AZWHFTKIBIQKCA-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229920001893 acrylonitrile styrene Polymers 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 229910021417 amorphous silicon Inorganic materials 0.000 description 1
- 125000005577 anthracene group Chemical group 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 1
- 125000005110 aryl thio group Chemical group 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- MGIAHHJRDZCTHG-UHFFFAOYSA-N benzene-1,3-dicarboxylic acid;terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1.OC(=O)C1=CC=CC(C(O)=O)=C1 MGIAHHJRDZCTHG-UHFFFAOYSA-N 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical group C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000007766 curtain coating Methods 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 229920006242 ethylene acrylic acid copolymer Polymers 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation 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
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000002541 furyl group Chemical group 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
- 239000003292 glue Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 239000005457 ice water Substances 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
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000004492 methyl ester group Chemical group 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 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
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002916 oxazoles Chemical class 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 229920006287 phenoxy resin Polymers 0.000 description 1
- 239000013034 phenoxy resin Substances 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 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
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene 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
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- SCUZVMOVTVSBLE-UHFFFAOYSA-N prop-2-enenitrile;styrene Chemical compound C=CC#N.C=CC1=CC=CC=C1 SCUZVMOVTVSBLE-UHFFFAOYSA-N 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
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000007761 roller coating Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 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
- 230000003068 static effect Effects 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- 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 1
- NLDYACGHTUPAQU-UHFFFAOYSA-N tetracyanoethylene Chemical group N#CC(C#N)=C(C#N)C#N NLDYACGHTUPAQU-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
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 150000003557 thiazoles Chemical class 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
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 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
- 238000009423 ventilation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
- G03G5/0664—Dyes
- G03G5/0675—Azo dyes
- G03G5/0679—Disazo dyes
- G03G5/0681—Disazo dyes containing hetero rings in the part of the molecule between the azo-groups
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Photoreceptors In Electrophotography (AREA)
Abstract
Description
【発明の詳細な説明】
3、発明の詳細な説明
〔産業上の利用分野〕
本発明は新規な有機光導電体及びそれを用いた電子写真
感光体に関するものである。Detailed Description of the Invention 3. Detailed Description of the Invention [Field of Industrial Application] The present invention relates to a novel organic photoconductor and an electrophotographic photoreceptor using the same.
これまで、セレン、硫化カドミウム、酸化亜鉛などの無
機光導電体を感光成分として利用した電子写真感光体は
、公知である。Electrophotographic photoreceptors using inorganic photoconductors such as selenium, cadmium sulfide, and zinc oxide as photosensitive components have been known so far.
一方、特定の有機化合物が光導電性を示すことが発見さ
れてから、数多くの有機光導電体が開発されて来た。例
えば、ポIJ + N−ビニルカルバゾール、ポリビニ
ルアントラセンなどの有機光4電体が知られている。On the other hand, since it was discovered that certain organic compounds exhibit photoconductivity, many organic photoconductors have been developed. For example, organic phototetraelectric materials such as polyJ + N-vinylcarbazole and polyvinylanthracene are known.
この様な有機光導電体を用いた電子写真感光体は、バイ
ンダーを適当に選択することによって塗工で生産できる
ため、極めて生産性が高く、安価に提供でき、しかも有
機顔料の選択によって感光波長域を自在にコントロール
できる利点を有している反面、この感光体は感度と耐久
特性に難があるため、これまでに実用に至ったものは、
ごくわずかである。Electrophotographic photoreceptors using such organic photoconductors can be produced by coating by appropriately selecting a binder, so they are extremely productive and can be provided at low cost.Moreover, by selecting organic pigments, the photosensitive wavelength can be adjusted. Although this photoreceptor has the advantage of being able to freely control the area, it has problems with sensitivity and durability, so the ones that have been put into practical use so far are
Very little.
本発明の目的は、i規な有機光導電体を提供することに
ある。An object of the present invention is to provide an i-order organic photoconductor.
本発明の別の目的は、特定の有機光導電体を使用するこ
とによシ改善された写真特性を有する電子写真感光体を
提供することにあり、
これにより、実用的な高感度特性と繰り返し使用におけ
る安定した1ヒ位特性を有する電子写真感光体を提供す
ることにある。Another object of the present invention is to provide an electrophotographic photoreceptor with improved photographic properties through the use of a specific organic photoconductor, which provides practical high-sensitivity properties and repeatability. An object of the present invention is to provide an electrophotographic photoreceptor having stable first-position characteristics during use.
本発明の上記目的は、下記一般式CDに示す有機光導電
体によって達成される。The above objects of the present invention are achieved by an organic photoconductor represented by the following general formula CD.
式中R1は置換もしくは非置換の、アルキル基、アラル
キル基、アリール基複索環基及びアミノ基を表わし、具
体的には、メチル、エチル、プロピル等のアルキル基、
ヒドロキシメチル、ヒドロキシエチル等のヒドロキシア
ルキル基、メトキシメチル、エトキシメチル、エトキシ
エチル等のアルコキシアルキル基、シアノアルキル基、
アミノアルキル基、N−アルキルアミノアルキル基、
N、N−ソアルキルアミンアルキル基、ハロゲノ化アル
キル基、ベンジル、フェネチル等のアラルキル基、フェ
ニル基及び置換フェニル基、ナフチル基及び置換ナフチ
ル基、ピリジン、キノリン、ぺ/ジオキサゾール、ぺ/
ジチアゾール、ベンゾイミダゾール、ベンゾトリアゾー
ル、ジベンゾフラン、カルバゾールなどの1価の複素環
基(を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7、グロボキシ等のアルコキ
シ基、塩素、臭素、ヨウ素等のハロゲン原子、ニトロ基
、・ツメチルアミノ等の置換アミン基等があげられる)
ツメチルアミノ、ノエチルアミノ等の置換アミン基等を
あげることができる。またR 、Rはそれぞれ水素原
子、ハロゲン原子、シアン基、アルキル基、アルコキシ
基を表わす。Aは芳香族性を有するカプラー成分を表わ
し、好ましくはAが以下の一般式〔■〕〜CIV)で表
わされるカプラー成分から選択されることが望ましい。In the formula, R1 represents a substituted or unsubstituted alkyl group, aralkyl group, aryl group, multi-ring group, or amino group, specifically, an alkyl group such as methyl, ethyl, propyl, etc.
Hydroxyalkyl groups such as hydroxymethyl and hydroxyethyl, alkoxyalkyl groups such as methoxymethyl, ethoxymethyl and ethoxyethyl, cyanoalkyl groups,
aminoalkyl group, N-alkylaminoalkyl group,
N,N-soalkylamine alkyl groups, halogenated alkyl groups, aralkyl groups such as benzyl and phenethyl, phenyl groups and substituted phenyl groups, naphthyl groups and substituted naphthyl groups, pyridine, quinoline, pe/dioxazole, pe/
Monovalent heterocyclic groups such as dithiazole, benzimidazole, benzotriazole, dibenzofuran, and carbazole (substituents include alkyl groups such as methyl, ethyl, and propyl, alkoxy groups such as methoxy, ethoxy7, and globoxy, chlorine, bromine, Examples include halogen atoms such as iodine, nitro groups, and substituted amine groups such as trimethylamino)
Examples include substituted amine groups such as trimethylamino and noethylamino. Further, R and R each represent a hydrogen atom, a halogen atom, a cyan group, an alkyl group, or an alkoxy group. A represents a coupler component having aromatic properties, and is preferably selected from coupler components represented by the following general formulas [■] to CIV).
一般式(II)にてナフタレン環、アンスラセン環、カ
ルバゾール環、ノベンゾフラン環、ベンゾカルバゾール
環、キノリン環、インキノリン環等の芳香族炭化水素環
又は複素環を形成する残基を表わし、Yは以下の一般式
(、)〜(、)で表わされる基からなる群より選ばれる
基を表わす。In general formula (II), Y represents a residue forming an aromatic hydrocarbon ring or a heterocycle such as a naphthalene ring, anthracene ring, carbazole ring, nobenzofuran ring, benzocarbazole ring, quinoline ring, inquinoline ring, etc. Represents a group selected from the group consisting of groups represented by the following general formulas (,) to (,).
(a) −CONR2R3
(b) −CONHNR4R5
(c) −CONHN=CH−Ar
一般式(&)においてR2は水素原子、メチル、エチル
、プロピル、ブチル、2−ヒドロキクエチル、3−ヒド
ロキシプロピル等の置換又は非置換のアルキル基、フェ
ニル、ナフチル等のアリール基から成る群より選ばれた
基、R31dメチル、エチル、プロピル、グチル、2−
ヒドロキシエチル、3−ヒドロキシプロピル等の置換又
は非tmのアルキル基、フェニル、ナフチル等のアリー
ル基及びピリノル、キノリル、カルバグリル、チアグリ
ル等の複素環残基から成る群より選ばれた基を表わす。(a) -CONR2R3 (b) -CONHNR4R5 (c) -CONHN=CH-Ar In the general formula (&), R2 is a hydrogen atom, methyl, ethyl, propyl, butyl, 2-hydroxyethyl, 3-hydroxypropyl, etc. A group selected from the group consisting of substituted or unsubstituted alkyl groups, aryl groups such as phenyl and naphthyl, R31d methyl, ethyl, propyl, butyl, 2-
It represents a group selected from the group consisting of substituted or non-tm alkyl groups such as hydroxyethyl and 3-hydroxypropyl, aryl groups such as phenyl and naphthyl, and heterocyclic residues such as pyrinol, quinolyl, carbaglyl and thiagylyl.
一般式(b)においてR4,R,、は置換又は非置換の
フェニル、ナフチル等のアリール基を表わす)を表わす
。上記R2〜R5における置換基として、メチル、エチ
ル等のアルキル基、フッ素、塩素、臭素等のハロゲン原
子、メトキシ、エトキシ等のアルコキシ基、アセチル、
ベンゾイル等のアシル基、メチルチオ、エチルチオ等の
アルキルチオ基、フェニルチオ等のアリールチオ基、フ
ェニル等のアリール基、ベンジル等のアラルキル基、ニ
トロ基、シアノ基、ツメチルアミノ、ジエチルアミノ、
ジペンノルアミノ、エチルアミノ等の置換アミン基等が
あげられる。一般式(c)においてArは置換基を有し
てもよいフェニル基、ナフチル基、アントリル基、ピリ
ジル基、チェニル基、フリル基、カルバゾリル基からな
る群から選ばれる基を表わす。一般式(d)においてR
6及びR7は夫々置換基を有してもよいアルキル基又は
アリール基を表わす。一般式(、)においは複素環基を
表わす。In the general formula (b), R4, R, represents a substituted or unsubstituted aryl group such as phenyl or naphthyl. Examples of substituents in R2 to R5 above include alkyl groups such as methyl and ethyl, halogen atoms such as fluorine, chlorine, and bromine, alkoxy groups such as methoxy and ethoxy, acetyl,
Acyl groups such as benzoyl, alkylthio groups such as methylthio and ethylthio, arylthio groups such as phenylthio, aryl groups such as phenyl, aralkyl groups such as benzyl, nitro groups, cyano groups, trimethylamino, diethylamino,
Examples include substituted amine groups such as dipenolamino and ethylamino. In the general formula (c), Ar represents a group selected from the group consisting of a phenyl group, a naphthyl group, an anthryl group, a pyridyl group, a chenyl group, a furyl group, and a carbazolyl group, which may have a substituent. In general formula (d), R
6 and R7 each represent an alkyl group or an aryl group which may have a substituent. General formula (,) represents a heterocyclic group.
一般式(c)のArの置換基としてはメチル基、エチル
基などのアルキル基;メトキシ基、エトキシ基などのア
ルコキシ基;アセチル基、ベンゾイル基ナトのアシル基
;ツメチルアミン基、ジエチルアミノ基などのアルキル
アミノ基;メチルエステル基、エチルエステル基のよう
なアルキルエステル基;フェニルエステル基;フェニル
カルバモイル基;ニトロ基;シアノ基などが挙げられる
。Arはこれらの置換基を2つ以上有してもよく、その
際置換基は互いに同じでも異なっていてもよい。一般式
(d)のR6,R,の置換基としては一般式(c)で表
わされるArにおける置換基が挙げられる。一般式(、
)は置換基を有してもよく、置換基としては一般式(c
)で表わされるArにおける置換基などが挙げられる。Substituents for Ar in general formula (c) include alkyl groups such as methyl and ethyl groups; alkoxy groups such as methoxy and ethoxy groups; acyl groups such as acetyl and benzoyl groups; alkyl groups such as trimethylamine and diethylamino groups. Examples include amino group; alkyl ester group such as methyl ester group and ethyl ester group; phenyl ester group; phenylcarbamoyl group; nitro group; cyano group. Ar may have two or more of these substituents, and in this case, the substituents may be the same or different. Examples of the substituents for R6 and R in general formula (d) include the substituents for Ar represented by general formula (c). General formula (,
) may have a substituent, and the substituent is the general formula (c
) and the like can be mentioned.
一般式〔■〕、〔■〕は
8R8
で表わされる。式中R8t−1置換又は非置換のアルギ
ル基、フェニル基、ナフチル基等のアリール基から成る
群より辿ばれた基を表わす。更に具体的にU、R8はメ
チル、エチル、プロピル等のアルキル基、ヒドロキンメ
チル、ヒドロキシエチル等のヒドロキシアルキル基、メ
トキシメチル、エトキシメチル、エトキシエチル等のア
ルコキシアルキル基、シアノアルキル基、アミノアルキ
ル基、N−アルキルアミノアルキル基、N、N−ジアル
キルアミノアルキル基、ハロゲン化アルキル基、ベンジ
ル、フェネチル等のアラルキル基、フェニル基及び置換
フェニル基、ナフチル基、置換ナフチル基、(置換基と
しては一般式〔■〕中のR2−R5における置換基があ
げられる)等があげられる。General formulas [■] and [■] are represented by 8R8. In the formula, R8t-1 represents a group consisting of a substituted or unsubstituted aryl group such as an argyl group, a phenyl group, or a naphthyl group. More specifically, U and R8 are alkyl groups such as methyl, ethyl, and propyl, hydroxyalkyl groups such as hydroquinemethyl and hydroxyethyl, alkoxyalkyl groups such as methoxymethyl, ethoxymethyl, and ethoxyethyl, cyanoalkyl groups, and aminoalkyl groups. groups, N-alkylaminoalkyl groups, N,N-dialkylaminoalkyl groups, halogenated alkyl groups, aralkyl groups such as benzyl and phenethyl, phenyl groups and substituted phenyl groups, naphthyl groups, substituted naphthyl groups, (substituents include Examples include substituents at R2-R5 in general formula [■]).
本発明の代表的な有機光導電体としては下記のシスアゾ
顔料を挙げることができる。Typical organic photoconductors of the present invention include the following cis-sazo pigments.
ベ 賀 顎
′4 国 〈
ば)
O襖
璽
顎 顎
(d 滅以上20種の
化合物を例示したが本発明の有機光導電体はそれに限定
されるものではない。bega chin'4 country 〈 ba)
O sliding door
Although more than 20 types of compounds are illustrated, the organic photoconductor of the present invention is not limited thereto.
これらのジスアゾ顔料は、1種または2種以上組合せて
用いることができる。また、これらの顔料は、例えば一
般式
(式中81は一般式〔l〕中の81と同じ意味を有する
。)で示されるジアミンを常法によりテトラゾ化し、次
いで対応するカプラーをアルカリの存在下にカップリン
グするか、または前記のジアミンのテトラゾニウム塩を
ホウフッ化塩あるいは塩化亜鉛複塩等の形で一旦単離し
た後、適当な溶媒例えばN、N−ツメチルホルムアミド
、ツメチルスルホキシド等の溶媒中でアルカリの存在下
にカッグラ−と力、ブリングすることにより容易に製造
することができる。These disazo pigments can be used alone or in combination of two or more. In addition, these pigments can be obtained by, for example, tetrazotizing a diamine represented by the general formula (81 in the formula has the same meaning as 81 in the general formula [l]) by a conventional method, and then converting the corresponding coupler in the presence of an alkali. or once the tetrazonium salt of the diamine is isolated in the form of borofluoride salt or zinc chloride double salt, etc., a suitable solvent such as N,N-trimethylformamide, trimethylsulfoxide, etc. It can be easily produced by stirring in the presence of an alkali in the presence of an alkali.
次に、本発明で用いるシスアゾ顔料の代表的な合成例を
下記に示す。Next, a typical synthesis example of the cis-sazo pigment used in the present invention is shown below.
合成例1 (前記例示のシスアゾ顔料)版1の合成)3
00dビーカーに水150itJ、濃塩酸11.3(0
,019モル)を入れ、氷水沿で冷却しながら攪拌し、
液温を3℃とした。次に亜硝酸ンーグ2、75 f!(
0,040%ル)を水5r!tlに溶かした液を液温を
5〜10℃の範囲にコントロールしながら10分間で滴
下し、滴下終了後、同温度で更に30分攪拌した。反応
液にカーボンを加え濾過してテトラゾ化液を得た。Synthesis Example 1 (Synthesis of the above-exemplified cis-sazo pigment) version 1) 3
In a 00d beaker, add 150 itJ of water and 11.3 liters of concentrated hydrochloric acid (0
, 019 mol) and stirred while cooling on ice water.
The liquid temperature was 3°C. Next, nitrous acid nug 2, 75 f! (
0,040%) in 5 liters of water! The solution dissolved in tl was added dropwise over 10 minutes while controlling the liquid temperature within the range of 5 to 10°C, and after the dropwise addition was completed, the mixture was further stirred at the same temperature for 30 minutes. Carbon was added to the reaction solution and filtered to obtain a tetrazotized solution.
次に1ノビ−カーに水500 tnlを入れ、苛性ソー
ダ−14,1F C0,354モル)を溶解した後、ナ
7)−ルAs(3−ヒドロキシ−2−ナフトエ酸アニリ
ド) 10.58 (0,040モル)を添加して溶解
した。Next, put 500 tnl of water into one beaker and dissolve 14.1F (CO, 354 mol) of caustic soda. ,040 mol) was added and dissolved.
このカプラー溶液を5℃に冷却し液温を5〜10℃にコ
ントロールしながら前述のテトラゾ化液を30分かけて
攪拌滴下して、その後室温で2時間攪拌した。反応液を
濾過後、水洗し粗製顔料14.0gを得た。次に、30
0rILlのN、N−ジメチルホルムアミドで5回洗浄
しアセトンで置換した後、室温で減圧乾燥し精製顔料1
3.21iを得た。収率は85.2%であった。This coupler solution was cooled to 5° C., and while controlling the liquid temperature at 5 to 10° C., the above-mentioned tetrazotized solution was added dropwise with stirring over 30 minutes, and then stirred at room temperature for 2 hours. The reaction solution was filtered and washed with water to obtain 14.0 g of a crude pigment. Next, 30
After washing with 0rILl N,N-dimethylformamide 5 times and replacing with acetone, the purified pigment 1 was dried under reduced pressure at room temperature.
3.21i was obtained. The yield was 85.2%.
元素分析
計算値(%) 実験値(%)
C72,1371,98
H4,084,22
N 12.02 12.
18合成例2 (前記例示のジスアゾ顔料&2の合成)
150ゴ、濃塩酸9.2 +nl (0,104モル)
に溶解した液に亜硝酸ソーダ2.46.9 (0,03
57モル)を水5ゴに溶解した液を液温0〜5℃に保ち
ながら10分間で滴下し、その後同温度で30分攪拌し
、カーR7戸遇した。この液にホウフッ化ソーダ5.6
:i(0,055モル)を水5Qdに溶解した液を30
分で滴下し、上記ノアミンのテトラゾ化物なホウフッ化
塩として単離し、冷水で2回洗浄した。ホウフッ化塩収
量6.731(収車80.0%)11ビーカーにDMF
500ゴ、
れ溶液とし、液温’a−10℃とした後先に合成したホ
ウフッ化塩5.0.9 (0,01モル)を加え、攪拌
溶解し、さらに酢酸ソーダ1.9.9 (0,0233
モル)を水5dに溶解した液を5分間で滴下し滴下後2
時間攪拌して顔料を戸数した。得られた顔料なりMFで
ソックスし、精製′?:10時間おこない、その後アセ
トンで置換して減圧乾燥した。収量8.5y(収率92
.9%)
元素分析
計算値(%) 実験値(%)
C65,6465,42
I(3,643,81
N 10.72 10.74CL
7.75 7.86以上2種類の顔料の
合成法について述べたが一般式〔I〕で示される他のジ
スアゾ顔料も同様にして合成される。Elemental analysis calculated value (%) Experimental value (%) C72,1371,98 H4,084,22 N 12.02 12.
18 Synthesis Example 2 (Synthesis of the exemplified disazo pigment &2)
150g, concentrated hydrochloric acid 9.2 +nl (0,104 mol)
Sodium nitrite 2.46.9 (0.03
A solution prepared by dissolving 57 mol) of water in 5 g of water was added dropwise over 10 minutes while keeping the liquid temperature at 0 to 5°C, and then stirred at the same temperature for 30 minutes and poured into 7 cars. Add 5.6% of sodium borofluoride to this solution.
:I (0,055 mol) dissolved in 5Qd of water was dissolved in 30
It was isolated as a tetrazotated borofluoride salt of the above noamine and washed twice with cold water. Borofluoride salt yield 6.731 (80.0%) DMF in 11 beakers
500 g was added to make a solution, and after bringing the liquid temperature to 'a-10°C, 5.0.9 (0.01 mol) of the borofluoride salt synthesized earlier was added, stirred and dissolved, and then 1.9.9 mol of sodium acetate was added. (0,0233
2 moles) dissolved in 5 d of water was added dropwise over 5 minutes.
The pigment was mixed by stirring for several hours. The obtained pigment was socked with MF and purified. : After 10 hours, the mixture was replaced with acetone and dried under reduced pressure. Yield 8.5y (Yield 92
.. 9%) Elemental analysis calculated value (%) Experimental value (%) C65,6465,42 I (3,643,81 N 10.72 10.74CL
7.75 7.86 Although the methods for synthesizing two types of pigments have been described above, other disazo pigments represented by general formula [I] can be synthesized in the same manner.
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、その電荷発生物質として前記一
般式(1)に示す有機光導電体を用いることができる。In a preferred embodiment of the present invention, the photosensitive layer is functionally separated into a charge generation layer and a charge transport layer, and the organic photoconductor represented by the general formula (1) can be used as the charge generation substance.
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
ャリアの飛程を短かくするために、薄膜層、例えば5ミ
クロン以下、好ましくは0.01ミクロン〜1ミクロン
の膜厚をもつ薄膜層とすることが望ましい。このこと多
くの電荷キャリアを生成すること、さらに発生した電荷
キャリアを再結合や捕獲(ドラッグ)によシ失活するこ
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。The charge generation layer contains as much of the organic photoconductor as possible in order to obtain sufficient absorbance and is preferably a thin film layer, for example less than 5 microns, in order to shorten the range of the generated charge carriers. It is desirable to form a thin film layer having a thickness of 0.01 micron to 1 micron. This is due to the need to generate a large number of charge carriers and to inject the generated charge carriers into the charge transport layer without being deactivated by recombination or capture (drag).
電荷発生層は、前述の有機光導電体を適尚なバインダー
に分散させ、これを基体の上に塗工することによって形
成でき、また真空蒸着装置により蒸着膜を形成すること
によって得ることができる。The charge generating layer can be formed by dispersing the above-mentioned organic photoconductor in a suitable binder and coating it on the substrate, or can be obtained by forming a deposited film using a vacuum deposition apparatus. .
上記バインダー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
、ボリアリレート(ビスフェノールAと7タル酸の縮重
合体など)ポリカーゴネート、ポリエステル、フェノキ
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、ポリビニルピリノン、セルロ
ースIIUW、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、ポリビニルピ電荷発生層中に
含有する樹脂は、80重量%以下、好ましくは40.i
ii%以下が適している。The binder can be selected from a wide range of insulating resins and organic photoconductive polymers such as poly-N-vinylcarbazole, polyvinylanthracene and polyvinylpyrene. Preferably, polyvinyl butyral, polyarylate (condensation polymer of bisphenol A and heptalic acid, etc.) polycargonate, polyester, phenoxy resin, polyvinyl acetate, acrylic resin, polyacrylamide resin, polyamide, polyvinylpyrinone, cellulose IIUW, Urethane resin, epoxy resin, casein, polyvinyl alcohol, polyvinyl P resin contained in the charge generation layer is 80% by weight or less, preferably 40% by weight. i
ii% or less is suitable.
これらの樹脂を溶解する溶剤は樹脂の種類によって異な
シまた下達の電荷輸送層や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、イングロビルアルコール等のア
ルコール類、アセトン、メチルエチルケトン、シクロヘ
キサノン等のケトン類N、N−ジメチルホルムアミド、
N、N−ツ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7
ラン、ジオキサン、エチレングリコールモ)1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、リグロイン、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。The solvent that dissolves these resins varies depending on the type of resin, and it is preferable to select a solvent that does not dissolve the underlying charge transport layer or subbing layer. Specific organic solvents include alcohols such as methanol, ethanol, and inglobil alcohol, ketones such as acetone, methyl ethyl ketone, and cyclohexanone, N,N-dimethylformamide,
Amides such as N,N-trimethylacetamide, sulfoxides such as dimethyl sulfoxide, tetrahydro7
ethyl ether, esters such as methyl acetate, ethyl acetate, aliphatic halogenated hydrocarbons such as chloroform, methylene chloride, dichloroethylene, carbon tetrachloride, trichlorethylene, etc. Aromatics such as benzene, toluene, xylene, ligroin, monochlorobenzene, dichlorobenzene, etc. can be used.
塗エバ、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、ヒート:r−ティング法
、マイヤーバーコーティング法、フ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
などのコーティ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、30℃〜200℃の温度で5分〜
2時間の範囲で静止または送風下で行なうことができる
。This can be done using coating methods such as coating evaporation, dip coating, spray coating, spinner coating, heat r-ting, Mayer bar coating, Fleid coating, roller coating, and curtain coating. . For drying, it is preferable to dry to the touch at room temperature and then heat dry. Heat drying at a temperature of 30℃ to 200℃ for 5 minutes or more
It can be carried out stationary or under ventilation for a period of 2 hours.
電荷輸送層は、前述の電荷発生層と電気的に接続されて
おυ、電界の存在下で電荷発生層から注入された電荷キ
ャリアを受は取るとともに、これらの電荷キャリアを表
面まで輸送できる機能を有している。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。The charge transport layer is electrically connected to the charge generation layer described above and has the function of receiving and receiving charge carriers injected from the charge generation layer in the presence of an electric field and transporting these charge carriers to the surface. have. 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.
光導電体は、一般に電荷キャリアを輸送する機能を有し
ているので、電荷輸送層はこの光導電体くよって形成で
きる。Since a photoconductor generally has the function of transporting charge carriers, a charge transport layer can be formed by using this photoconductor.
電荷輸送層における電荷キャリアを輸送する物質(以下
、単に電荷輸送物質という)は、前述の電荷発生層が感
応する電磁波の波長域に実質的に非感応性であることが
好ましい。ここで言う「電磁波」とは、γ線、X線、紫
外線、可視光線、近赤外線、赤外線速、赤外線などを包
含する広義の「光線」の定義を包含する。電荷輸送層の
光感応性波長域が電荷発生層のそれと一致またはオーバ
ーラツプする時には、両者で発生した電荷キャリアが相
互に捕獲し合い、結果的には感度の低下の原因となる。The substance that transports charge carriers in the charge transport layer (hereinafter simply referred to as charge transport substance) is preferably substantially insensitive to the wavelength range of electromagnetic waves to which the charge generation layer is sensitive. The term "electromagnetic waves" as used herein includes a broad definition of "light rays" that includes gamma rays, X-rays, ultraviolet rays, visible light, near infrared rays, infrared rays, infrared rays, and the like. When the photosensitive wavelength range of the charge transport layer coincides with or overlaps that of the charge generation layer, charge carriers generated in both layers trap each other, resulting in a decrease in sensitivity.
電荷輸送物質には電子輸送性物質と正孔輸送性物質がち
や、電子輸送性物質としては、クロルアニル、ブロモア
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、2
.4.7− トリニトロ−9−ノシアノメチレンフルオ
レノン、2,4,5.7−チトラニトロキサントン、2
+418−) !jニトロチオキサント7等の電子吸引
性物質やこれら電子吸引物質を高分子化したもの等があ
る。Charge transport substances include electron transport substances and hole transport substances, and electron transport substances include chloranil, bromoanil, tetracyanoethylene, tetracyanoquino dimethane, and 2.4.7-trinitro-9-fluorenone. ,
2,4,5.7-tetranitro-9-fluorenone, 2
.. 4.7-trinitro-9-nocyanomethylenefluorenone, 2,4,5.7-titranitroxanthone, 2
+418-)! Examples include electron-withdrawing substances such as j-nitrothioxant 7 and polymerized versions of these electron-withdrawing substances.
正孔輸送性物質としては、ピレン、N−エチルカルバゾ
ール、N−イソプロピルカルバソール、N−メチル−N
−フェニルヒドラツノ−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、 N、N−ジフェニ
ルヒドラNノー3−メチリデン−10−エチルフェノチ
アジン、N、N −ジフェニルヒドラジノ−3−メチリ
デン−10−二チルフェノキサノン、P−ゾエチルアミ
ノペンズアルデヒドーN、N−ゾフェニルヒドラゾン、
P−ゾエチルアミノペンズアルデヒドーN−α−ナフチ
ル−N−7エニルヒドラゾン、P−ピロリジノベンズア
ルデヒド−N、N−ジフェニルヒドラゾン。Examples of hole-transporting substances include pyrene, N-ethylcarbazole, N-isopropylcarbazole, N-methyl-N
-Phenylhydrazino-3-methylidene-9-ethylcarbazole, N,N-diphenylhydrazino-3-methylidene-9-ethylcarbazole, N,N-diphenylhydrano-3-methylidene-10-ethylphenothiazine, N, N-diphenylhydrazino-3-methylidene-10-ditylphenoxanone, P-zoethylaminopenzaldehyde N, N-zophenylhydrazone,
P-zoethylaminopenzaldehyde N-α-naphthyl-N-7enylhydrazone, P-pyrrolidinobenzaldehyde-N,N-diphenylhydrazone.
11313− トリメチルインドレニン−ω−アルデヒ
ド−N、N−ジフェニルヒドラゾ7、P−ジエチル4ベ
ンズアルデヒドー3−メチルベンズチアゾリノン−2−
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dF”j−)
7ソール、1−フェニル−3−(P−ジエチルアミノス
テリル)−5−(P−ジエチルアミノフェニル)ピラゾ
リン、に〔キノリル(2) ) −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、1−〔ピリジル(2) :] −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、1−〔6−メドキシーピリ
ノル(2))−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、1−
〔ピリジル(3) ) −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、1−〔レピジル(2) :] −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、1−〔ピリノル(2))−3−
(P−ジエチルアミノスチリル)−4−メチル−5−(
P−ジエチルアミノフェニル)ピラゾリン、1−〔ピリ
ジル(2) 〕−3−(α−メチル−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、1−フェニル−3−(P−ジエチルアミノス
チリル)−4−メチル−5−(p−ジエチルアミノフェ
ニル)ピラゾリン、1−フェニル−3−(α−ベンジル
−P−ジエチルアミノスチリル)−5−(P−−、’エ
チルアミノフェニル)ピラゾリン、スピロビジゾリンな
どのピラゾリ/類、2−(P−ジエチルアミノスチリル
)−6−ジエチルアミノベンズオキサゾール、2−(P
−ジエチルアミンフェニル)−4−(P−ジメチルアミ
ノフェニル)−5−(2−クロロフェニル)オキサゾー
ル等のオキサゾール系化合物、2−(P−ジエチルアミ
ノスチリル)−6−ジニチルアミノペンゾチアゾール等
のチアゾール系化合物、ビス(4−ジエチルアミノ−2
−メチルフェニル)−フェニルメタン等のトリアリール
メタン系化合物、1.1−ビス(4−N、N −ジエチ
ルアミノ−2−メチルフェニル)へブタン、1.1,2
.2−テトラキス(4−N、N−ジメチルアミノ−2−
メチルフェニル)エタン等のポリアリールアルカン類、
トリフェニルアミン、ポリ−N −ビニルカルバゾール
、ポリビニルピレン、ポリビニルアントラセン、ポリビ
ニルアクリ・シン、ポリ−9−ビニルフェニルアントラ
セン、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等がある。11313- Trimethylindolenine-ω-aldehyde-N,N-diphenylhydrazo 7, P-diethyl 4-benzaldehyde 3-methylbenzthiazolinone-2-
Hydrazones such as hydrazone, 2,5-bis(p-diethylaminophenyl)-1,3,4-odF"j-)
7sol, 1-phenyl-3-(P-diethylaminosteryl)-5-(P-diethylaminophenyl)pyrazoline, ni[quinolyl(2))-3-(P-diethylaminostyryl)-5-(P-diethylamino phenyl)pyrazoline, 1-[pyridyl(2):] -3-(
P-diethylaminostyryl)-5-(P-diethylaminophenyl)pyrazoline, 1-[6-medoxypyrinol(2))-3-(P-diethylaminostyryl)-
5-(P-diethylaminophenyl)pyrazoline, 1-
[Pyridyl (3)) -3-(P-diethylaminostyryl)-5-(P-diethylaminophenyl)pyrazoline, 1-[Lepidyl (2):] -3-(P-・
diethylaminostyryl)-5-(P-diethylaminophenyl)pyrazoline, 1-[pyrinol(2))-3-
(P-diethylaminostyryl)-4-methyl-5-(
P-diethylaminophenyl)pyrazoline, 1-[pyridyl(2)]-3-(α-methyl-P-diethylaminostyryl)-5-(P-diethylaminophenyl)pyrazoline, 1-phenyl-3-(P-diethylaminostyryl) )-4-methyl-5-(p-diethylaminophenyl)pyrazoline, 1-phenyl-3-(α-benzyl-P-diethylaminostyryl)-5-(P--,'ethylaminophenyl)pyrazoline, spirobidizoline, etc. Pyrazoli/s, 2-(P-diethylaminostyryl)-6-diethylaminobenzoxazole, 2-(P-diethylaminostyryl)-6-diethylaminobenzoxazole,
Oxazole compounds such as -diethylaminephenyl)-4-(P-dimethylaminophenyl)-5-(2-chlorophenyl)oxazole, thiazole compounds such as 2-(P-diethylaminostyryl)-6-dinithylaminopenzothiazole Compound, bis(4-diethylamino-2
triarylmethane compounds such as -methylphenyl)-phenylmethane, 1.1-bis(4-N,N-diethylamino-2-methylphenyl)hebutane, 1.1,2
.. 2-tetrakis(4-N,N-dimethylamino-2-
polyarylalkane such as methylphenyl)ethane,
Examples include triphenylamine, poly-N-vinylcarbazole, polyvinylpyrene, polyvinylanthracene, polyvinylacrysine, poly-9-vinylphenylanthracene, pyrene-formaldehyde resin, ethylcarbazole formaldehyde resin, and the like.
これらの有機電荷輸送物質の他に、セレン、セレン−テ
ルルアモルファスシリコン、硫化カドミウムなどの無機
材料も用いることができる。In addition to these organic charge transport materials, inorganic materials such as selenium, selenium-tellurium amorphous silicon, and cadmium sulfide can also be used.
また、これらの電荷輸送物質は、1種または2種以上組
合せて用いることができる。Further, these charge transport substances can be used alone or in combination of two or more.
電荷輸送物質が成膜性を有していない時には、適当なバ
インダーを選択することによって被膜形成できる。バイ
ンダーとして使用できる樹脂は、例えばアクリル樹脂ボ
リアリレート、ポリエステル、ポリカーボネート、ポリ
スチレンアクリロニトリルースチレンコホリマー、アク
リロニトリル−ブタジェンコポリマー、ポリビニルブチ
ラール、ポリビニルホルマール、ポリスルホン、ポリア
クリルアミド、ポリアミド、塩素化ゴムなどの絶縁性樹
脂、あるいはポリ−N−ビニルカルバゾール、ポリビニ
ルアントラセン、ポリビニルピレンなどの有機光導電性
、41Jマーを挙げることができる。When the charge transport material does not have film-forming properties, a film can be formed by selecting an appropriate binder. Resins that can be used as binders include, for example, acrylic resin polyarylate, polyester, polycarbonate, polystyrene acrylonitrile styrene copolymer, acrylonitrile-butadiene copolymer, polyvinyl butyral, polyvinyl formal, polysulfone, polyacrylamide, polyamide, insulating rubber such as chlorinated rubber. Examples include resins, organic photoconductors such as poly-N-vinylcarbazole, polyvinylanthracene, polyvinylpyrene, and 41J-mer.
電荷輸送層は、電荷キャ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、5ミクロン〜30ミクロンであるが、好ましい範
囲は8ミクロン〜20ミクロンでおる。塗工によって電
荷輸送層を形成する際には、前述した様に適当なコーテ
ィング法を用いることができる。Since the charge transport layer has a limit in its ability to transport charge carriers, it cannot be made thicker than necessary. Generally, the range is 5 microns to 30 microns, with a preferred range of 8 microns to 20 microns. When forming the charge transport layer by coating, an appropriate coating method can be used as described above.
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、導電層を有する基体の上に設けられる。導tS
を有する基体としては、基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、パナノウム、モリプデ/、クロム、チタン、
二、ケル、インジウム、金や白金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
真空蒸着法によって被膜形成された層を有するプラスチ
、り(例えば、ポリエチレン、ポリプロピレン、ポリ塩
化ビニル、ぼりエチレンテレフタレート、アクリル樹脂
、ポリ7ツ化エチレンなど)、導電性粒子(例えば、カ
ーノンブラック、銀粒子など)を適当なバインダーとと
もにプラスチックの上に被覆した基体、導電性粒子をプ
ラスチ、りや紙に含浸した基体や導電性ポリマーを有す
るプラスチックなどを用いることができる。A photosensitive layer having such a laminated structure of a charge generation layer and a charge transport layer is provided on a substrate having a conductive layer. Guide tS
Substrates that have conductivity include those that have conductivity themselves;
For example, aluminum, aluminum alloy, copper, zinc, stainless steel, pananoum, molybdenum, chromium, titanium,
2. Plasti, which can use metal, indium, gold, platinum, etc., and has a layer formed by vacuum deposition of aluminum, aluminum alloy, indium oxide, tin oxide, indium oxide-tin oxide alloy, etc.; (e.g., polyethylene, polypropylene, polyvinyl chloride, ethylene terephthalate, acrylic resin, poly7tethylene, etc.), conductive particles (e.g., carnon black, silver particles, etc.) are placed on top of the plastic with a suitable binder. Coated substrates, substrates impregnated with conductive particles in plasti, glue or paper, plastics with conductive polymers, etc. can be used.
導電層と感光層の中間に、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。下引層ハ、力ぜイン、
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って形成できる。A subbing layer having barrier and adhesive functions can also be provided between the conductive layer and the photosensitive layer. The lower layer, the force,
Polyvinyl alcohol, nitrocellulose, ethylene-
Acrylic acid copolymer, polyamide (nylon 6, nylon 66, nylon 610, copolymerized nylon, alkoxymethylated nylon, etc.), polyurethane, gelatin,
It can be formed from aluminum oxide, aluminum, etc.
下引層の膜厚は、0.1ミクロン〜5ミクロン、好まし
くは0.5ミクロン〜3ミクロンが適当である。The thickness of the undercoat layer is suitably 0.1 micron to 5 micron, preferably 0.5 micron to 3 micron.
導電層、電荷発生層、電荷輸送層の順に積層した感光体
を使用する場合において電荷輸送物質が電子輸送性物質
からなるときは、電荷輸送層表面を正に帯電する必要が
あり、帯電後露光すると露光部では電荷発生層において
生成した電子が電荷輸送層に注入され、そのおと表面に
達して正電荷を中和し、表面電位の減衰が生じ未露光部
との間に静電コントラストが生じる。この様にしてでき
た静電潜像を負荷電性のトナーで現像すれば可視像が得
られる。これを直接定着するか、あるいはトナー像を紙
やプラスチックフィルム等に転写後、現像し定着するこ
とができる。When using a photoreceptor in which a conductive layer, a charge generation layer, and a charge transport layer are laminated in this order, and the charge transport material is an electron transport material, the surface of the charge transport layer must be positively charged, and exposure after charging is required. Then, in the exposed area, electrons generated in the charge generation layer are injected into the charge transport layer, reaching the surface and neutralizing the positive charge, causing a decrease in surface potential and creating an electrostatic contrast between it and the unexposed area. arise. A visible image can be obtained by developing the electrostatic latent image thus formed with a negatively charged toner. This can be directly fixed, or the toner image can be transferred to paper, plastic film, etc. and then developed and fixed.
また、感光体上の静電潜像を転写紙の絶縁層上に転写後
視像し、定着する方法もとれる。現像剤の種類や現像方
法、定着方法は公知のものを採用しても良く、特定のも
のに限定されるものでは々゛ い。Alternatively, a method may be used in which the electrostatic latent image on the photoreceptor is transferred onto an insulating layer of transfer paper, and then visually imaged and fixed. The type of developer, developing method, and fixing method may be any known ones, and are not limited to any specific ones.
一方、電荷輸送物質が正孔輸送物質から成る場合、電荷
輸送層表面を負に帯電する必要がちシ、帯電後、露光す
ると露光部では電荷発生層において生成した正孔が電荷
輸送層に注入され、その後表面に達して負電荷を中和し
、表面電位の減衰が生じ未露光部との間に静電コントラ
ストが生じる。On the other hand, when the charge transport material consists of a hole transport material, it is necessary to negatively charge the surface of the charge transport layer, and when exposed to light after charging, holes generated in the charge generation layer are injected into the charge transport layer in the exposed area. , which then reaches the surface and neutralizes the negative charges, resulting in attenuation of the surface potential and an electrostatic contrast between the surface potential and the unexposed area.
現像時には電子輸送物質を用いた場合とは逆に正電荷性
トナーを用いる必要がある。During development, it is necessary to use a positively charged toner, contrary to the case where an electron transport material is used.
本発゛明の別の具体例としては、前述の有機光導電体を
電荷輸送物質とともに同一層に含有させた電子写真感光
体を挙げることができる。この際、前述の電荷輸送物質
の他にボIJ−N−ビニルカルバ:/’−#トトリニト
ロフルオレノンからなる電荷移動錯化合物を用いること
ができる。Another specific example of the present invention is an electrophotographic photoreceptor in which the above-mentioned organic photoconductor is contained in the same layer together with a charge transport material. At this time, a charge transfer complex compound consisting of BoIJ-N-vinylcarba:/'-#totrinitrofluorenone can be used in addition to the charge transport substance described above.
この例の電子写真感光体は、前述の有機光導電体と電荷
移動錯化合物をテトラヒドロフランに溶解されたポリエ
ステル溶液中に分散させた婁、被膜形成させて調製でき
る。The electrophotographic photoreceptor of this example can be prepared by dispersing the organic photoconductor and charge transfer complex compound in a polyester solution dissolved in tetrahydrofuran to form a film.
いずれの感光体においても、用いる顔料は一般式(1)
で示されるジスアゾ顔料から選ばれる少なくとも1種類
の顔料を含有し、必要に応じて光吸収の異なる顔料を組
合せて使用した感光体の感度を高めたシ、・ゼンクロマ
チックな感光体を得るなどの目的で一般式(1)で示さ
れるジスアゾ顔料を2種類以上組合せた9、まだは公知
の染料、顔料から選ばれた電荷発生物質と組合せて使用
することも可能である。In any photoreceptor, the pigment used is of the general formula (1)
The sensitivity of the photoreceptor is increased by containing at least one type of pigment selected from the disazo pigments shown in the following, and pigments with different light absorptions are used in combination as necessary. For this purpose, it is also possible to use a combination of two or more disazo pigments represented by the general formula (1)9, or a charge generating substance selected from known dyes and pigments.
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やCRTプリンター等の
電子写真応用分野にも広く用いることができる。The electrophotographic photoreceptor of the present invention can be used not only in electrophotographic copying machines, but also in a wide range of electrophotographic applications such as laser printers and CRT printers.
まだ、本発明の有機光導電体は、前述の電子写真感光体
の他に、太陽電池や光センサーに用いることもできる。Furthermore, the organic photoconductor of the present invention can also be used in solar cells and optical sensors in addition to the above-mentioned electrophotographic photoreceptor.
太陽電池は、例えば酸化インジウムとアルミニウムによ
って前述の有機光′4iI!体をサンドイッチすること
によって調製できる。Solar cells can produce the aforementioned organic light '4iI!' using, for example, indium oxide and aluminum. It can be prepared by sandwiching the body.
以下、本発明を実施例に従って説明する。Hereinafter, the present invention will be explained according to examples.
実施例1
アルミ板上にカゼインのアンモニア水溶液(カゼイン1
1.2g28%アンモニア水Ig、水222M)をマイ
ヤーパーで、乾燥後の膜厚が1.0ミクロどとなる様に
塗布し、乾燥した。Example 1 Ammonia aqueous solution of casein (casein 1
1.2g of 28% ammonia water (Ig, water 222M) was applied using a Mayer Parr so that the film thickness after drying would be 1.0 microns, and dried.
次に、前記例示のジスアゾ顔料A1の有機光導電体5y
を、テトラヒドロフラン95m1にブチラール樹脂(ブ
チラール化度63モル%)2gを溶かした液に加え、ア
トライターで10時間分散した。この分散液を先に形成
したカゼイン層の上に乾燥後の膜厚が0.3ミクロンと
なる様にマイヤーパーで塗布し、乾燥して電荷発生層を
形成した。Next, an organic photoconductor 5y of the above-mentioned disazo pigment A1
was added to a solution prepared by dissolving 2 g of butyral resin (degree of butyralization: 63 mol %) in 95 ml of tetrahydrofuran, and dispersed with an attritor for 10 hours. This dispersion was applied onto the previously formed casein layer using a Mayer Par so that the film thickness after drying would be 0.3 microns, and dried to form a charge generation layer.
次いで、構造式
のヒドラゾン化合物5gとポリメチルメタクリレート樹
脂(数”F均分子zlOO,OOo )5f!をベンゼ
ン73mに溶解し、これを電荷発生層の上に乾燥後の膜
厚が12ミクロンとなる様にマイヤーパーで塗布し、乾
燥して電荷輸送層を形成した。Next, 5 g of a hydrazone compound having the structural formula and 5 f! of polymethyl methacrylate resin (number of molecules zlOO, OOo) were dissolved in 73 m of benzene, and this was placed on the charge generation layer so that the film thickness after drying was 12 microns. A charge transport layer was formed by applying the same coating using Mayer Per and drying.
この様にして作成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Mod@l SP−428を用いて
スタチック方式で−5kVでコロナ帯電し、暗所で1秒
間保持した後、照度5 tuxで露光し帯電特性を調べ
た。The electrophotographic photoreceptor thus prepared was statically charged with corona at -5 kV using an electrostatic copying paper tester Mod@l SP-428 manufactured by Kawaguchi Electric Co., Ltd., and held in a dark place for 1 second. It was exposed to light at an illuminance of 5 tux and the charging characteristics were examined.
帯電特性としては、表面電位(vo)と1秒間暗減衰さ
せた時の電位を捧に減衰するに必要な露光量(−)を測
定した。As for charging characteristics, the surface potential (vo) and the amount of exposure (-) required to attenuate the potential when dark decayed for 1 second were measured.
さらに、繰υ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、本実施例で作成した感光体を−5
,6kVのコロナ帯電器、照度5 tuxを有する露光
光学系、現像器、転写帯電器、除電露光光学系およびク
リーナーを備えた電子写真複写機のシリンダーに貼り付
けた。この複写機は、シリンダーの駆動に伴い、転写紙
上に画像が得られる構成になっている。この複写機を用
いて、初期の明部電位(vL)と暗部電位(VD)およ
び5000回使用した後の明部電位(vL)と暗部電位
(VD)を測定した。この結果を次に示す。Furthermore, in order to measure the fluctuations in bright area potential and dark area potential when repeatedly used, the photoreceptor prepared in this example was
, a 6 kV corona charger, an exposure optical system with an illuminance of 5 tux, a developing device, a transfer charger, a static elimination exposure optical system, and a cleaner. This copying machine is configured to produce an image on transfer paper as a cylinder is driven. Using this copying machine, the initial bright area potential (vL) and dark area potential (VD) and the bright area potential (vL) and dark area potential (VD) after 5000 uses were measured. The results are shown below.
V0ニー600ゲルト
Ey、 : 2.5 lux、 see初 期
5000回耐久後V ニー605.Nルト
VD ニー595&ルトV ニー11071+#ル
ト VLニー120&ルト実施例2〜20
実施例1で用いたジスアゾ顔料に代えて、第3表に示す
ジスアゾ顔料を用いたほかは、全〈実施例1と同様の方
法で電子写真感光体を作成した。V0 Knee 600 gelt Ey: 2.5 lux, see early
V knee after 5000 cycles 605. Nruto
VD Knee 595 & Ruto V Knee 11071 + #Ruto VL Knee 120 & Ruto Examples 2 to 20 Same as Example 1 except that the disazo pigment shown in Table 3 was used in place of the disazo pigment used in Example 1. An electrophotographic photoreceptor was prepared using the method described above.
各感光体の帯電特性と耐久特性を実施例1と同様の方法
によって測定した。これらの結果を次に示す。The charging characteristics and durability characteristics of each photoreceptor were measured in the same manner as in Example 1. These results are shown below.
実施例21
実施例1で作成した電荷発生層の上に、2.4.7−ド
リニトロー9−フルオレノン5gとポリ−4,4’−シ
オキシゾフェニルー2.2’−プロパンカーゲネート(
分子量300,000 ) 5 jiをテトラヒドロフ
ラン70′Itlに溶解して作成した塗布液を乾燥後の
塗工量が1097m となる様に塗布し、乾燥した。Example 21 On the charge generation layer prepared in Example 1, 5 g of 2.4.7-dolinitro-9-fluorenone and poly-4,4'-cyoxyzophenyl-2,2'-propanecargenate (
A coating solution prepared by dissolving 5ji (molecular weight: 300,000) in 70'Itl of tetrahydrofuran was applied to give a coating weight of 1097 m 2 after drying, and dried.
こうして作成した電子写真感光体を実施例1と同様の方
法で帯電測定を行なった。この時、帯電極性は中とした
。この結果を次に示す。The electrostatic charge of the electrophotographic photoreceptor thus prepared was measured in the same manner as in Example 1. At this time, the charging polarity was set to medium. The results are shown below.
VD:+610 ビルト
Ey2: 3.5 ]ux、sec初 期
5000回耐久後V :+60CJMkト
V。: +575 NルトV :+200ボル
ト V、:+220ゴルト実施例22
アルミ蒸着ポリエチレンテレフタレートフィルムのアル
ミ面上に膜厚1.1ミクロンのポリビニルアルコールの
被膜全形成した。VD: +610 Built Ey2: 3.5 ]ux, sec early
V after 5000 cycles: +60CJMk
V. : +575 N Volt V : +200 Volt V, : +220 Galt Example 22 A polyvinyl alcohol film having a thickness of 1.1 microns was entirely formed on the aluminum surface of an aluminum vapor-deposited polyethylene terephthalate film.
次に、実施例1で用いたジスアゾ顔料の分散液を先に形
成したポリビニルアルコール層の上ニ、乾燥後の膜厚が
0.5ミクロンとなる様にマイヤーパーで塗布し、乾燥
して電荷発生層を形成した。Next, the dispersion of the disazo pigment used in Example 1 was applied onto the previously formed polyvinyl alcohol layer using a Mayer perr so that the film thickness after drying was 0.5 microns, dried and charged. A generation layer was formed.
次いで、構造式
のピラゾリン化合物5Iとボリアリレート樹脂(ビスフ
ェノール人とテレフタル酸−イソフタル酸の縮重合体)
5gをテトラヒドロフラン7Q+aJに溶かした液を電
荷発生層の上に乾燥後の膜厚が10ミクロンとなる様に
塗布し、乾燥して電荷輸送層を形成した。Next, pyrazoline compound 5I of the structural formula and polyarylate resin (condensation polymer of bisphenol and terephthalic acid-isophthalic acid)
A solution obtained by dissolving 5 g of the solution in 7Q+aJ of tetrahydrofuran was applied onto the charge generation layer so that the film thickness after drying would be 10 microns, and dried to form a charge transport layer.
こうして調製した感光体の帯電特性および耐久特性を実
施例1と同様の方法によって測定した。The charging characteristics and durability characteristics of the photoreceptor thus prepared were measured in the same manner as in Example 1.
この結果を次に示す。The results are shown below.
V、ニー600 ボルト
Eη: 2・3敞゛6c
初 期 5ooo回耐久後’/D : −
605Nルト VDニー590ポルトV、、ニー]1
5フルト VLニー130ボルト実施例23
厚さ100ミクロノ厚のアルミ板上にカゼインのアンモ
ニア水層液を塗布し、乾燥して膜厚1.1ミクロンの下
引層を形成した。V, knee 600 volts Eη: 2.3 minutes 6c Initial After 5ooo cycles'/D: -
605N Ruto VD Knee 590 Porto V,, Knee] 1
5 fult VL knee 130 volts Example 23 An ammonia aqueous layer solution of casein was coated on an aluminum plate with a thickness of 100 microns and dried to form a subbing layer with a thickness of 1.1 microns.
次に、2,4.7− トリニトロ−9−フルオレノン5
g ト$ +) −N−ビニルカルバゾール< 数平
均分子量300,000 ) 511をテトラヒドロフ
ラン701Ltに溶かして電荷移動錯化合物を形成した
。この電荷移動錯化合物と前記例示のノスアゾ顔料A1
の光導電体1gを、ポリエステル樹脂(バイロン;東洋
紡製)5gをテトラヒドロフラン70−に溶かした液に
加え、分散した。この分散液全下引層の上に乾燥後の膜
厚が12ミクロンとなる様に塗布し、乾燥した。Next, 2,4,7-trinitro-9-fluorenone 5
g $+) -N-vinylcarbazole<number average molecular weight 300,000) 511 was dissolved in 701 Lt of tetrahydrofuran to form a charge transfer complex compound. This charge transfer complex compound and the above-mentioned nosazo pigment A1
1 g of the photoconductor was added to a solution in which 5 g of polyester resin (Vylon; manufactured by Toyobo) was dissolved in 70% of tetrahydrofuran, and dispersed. This dispersion was coated on the entire subbing layer so that the film thickness after drying was 12 microns, and dried.
こうした調製した感光体の帯!特性と耐久特性を実施例
1と同様の方法によって測定した・この結果を次に示す
。但し、帯電極性はeとした。These prepared photoreceptor strips! The properties and durability were measured by the same method as in Example 1.The results are shown below. However, the charging polarity was set to e.
本発明による特定の有機光導電体を用いた電子写真感光
体は、高感度特性と繰シ返し使用における安定した電位
特性を発揮することができる。The electrophotographic photoreceptor using the specific organic photoconductor according to the present invention can exhibit high sensitivity characteristics and stable potential characteristics during repeated use.
Claims (2)
る有機光導電体: ▲数式、化学式、表等があります▼〔 I 〕 (式中、Aは芳香族性を有するカプラー成分を表わし、
R_1は置換もしくは非置換の、アルキル基、アラルキ
ル基、アリール基、複素環基及びアミノ基を表わす。R
_1_1、R_1_2はそれぞれ水素原子、ハロゲン原
子、シアノ基、アルキル基、アルコキシ基を表わす。)(1) Organic photoconductor characterized by being represented by the following general formula [I]: ▲There are mathematical formulas, chemical formulas, tables, etc.▼[I] (In the formula, A represents a coupler component having aromaticity. ,
R_1 represents a substituted or unsubstituted alkyl group, aralkyl group, aryl group, heterocyclic group, or amino group. R
_1_1 and R_1_2 each represent a hydrogen atom, a halogen atom, a cyano group, an alkyl group, or an alkoxy group. )
る有機光導電体を含有する感光層を設けたことを特徴と
する電子写真感光体:(2) An electrophotographic photoreceptor characterized in that a photosensitive layer containing an organic photoconductor represented by the above general formula [I] is provided on a conductive support:
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP12685486A JPS62280851A (en) | 1986-05-30 | 1986-05-30 | Organic photoconductor and electrophotographic sensitive body using said photoconductor |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP12685486A JPS62280851A (en) | 1986-05-30 | 1986-05-30 | Organic photoconductor and electrophotographic sensitive body using said photoconductor |
Publications (1)
Publication Number | Publication Date |
---|---|
JPS62280851A true JPS62280851A (en) | 1987-12-05 |
Family
ID=14945490
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP12685486A Pending JPS62280851A (en) | 1986-05-30 | 1986-05-30 | Organic photoconductor and electrophotographic sensitive body using said photoconductor |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS62280851A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2017157743A (en) * | 2016-03-03 | 2017-09-07 | 日本放送協会 | Organic electroluminescent element material and organic electroluminescent element |
-
1986
- 1986-05-30 JP JP12685486A patent/JPS62280851A/en active Pending
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2017157743A (en) * | 2016-03-03 | 2017-09-07 | 日本放送協会 | Organic electroluminescent element material and organic electroluminescent element |
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