JPH03211559A - Electrophotographic sensitive body - Google Patents
Electrophotographic sensitive bodyInfo
- Publication number
- JPH03211559A JPH03211559A JP641190A JP641190A JPH03211559A JP H03211559 A JPH03211559 A JP H03211559A JP 641190 A JP641190 A JP 641190A JP 641190 A JP641190 A JP 641190A JP H03211559 A JPH03211559 A JP H03211559A
- Authority
- JP
- Japan
- Prior art keywords
- group
- charge
- electric charge
- formula
- layer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- -1 2-ethylphenyl Chemical group 0.000 claims abstract description 28
- 239000000049 pigment Substances 0.000 claims abstract description 21
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims abstract description 11
- 235000010290 biphenyl Nutrition 0.000 claims abstract description 9
- 239000004305 biphenyl Substances 0.000 claims abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims abstract description 7
- 125000005843 halogen group Chemical group 0.000 claims abstract description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims abstract 2
- 108091008695 photoreceptors Proteins 0.000 claims description 56
- 239000000126 substance Substances 0.000 claims description 24
- 125000005810 2,5-xylyl group Chemical group [H]C1=C([H])C(=C(*)C([H])=C1C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- 230000035945 sensitivity Effects 0.000 abstract description 16
- 239000000463 material Substances 0.000 abstract description 13
- 230000003595 spectral effect Effects 0.000 abstract description 7
- 230000010355 oscillation Effects 0.000 abstract description 6
- 238000000034 method Methods 0.000 abstract description 5
- 229910052736 halogen Inorganic materials 0.000 abstract description 3
- 150000002367 halogens Chemical group 0.000 abstract description 2
- 230000000052 comparative effect Effects 0.000 description 18
- 238000000576 coating method Methods 0.000 description 11
- 238000001035 drying Methods 0.000 description 7
- 239000011230 binding agent Substances 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 238000012546 transfer Methods 0.000 description 5
- 239000002800 charge carrier Substances 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 239000010408 film Substances 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-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
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 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
- 230000000694 effects Effects 0.000 description 3
- 210000003127 knee Anatomy 0.000 description 3
- 229910017604 nitric acid Inorganic materials 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 229920002382 photo conductive polymer Polymers 0.000 description 3
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 3
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 3
- 229920000178 Acrylic resin Polymers 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000004677 Nylon Substances 0.000 description 2
- 229920002292 Nylon 6 Polymers 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000005018 casein Substances 0.000 description 2
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 2
- 235000021240 caseins Nutrition 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229920001778 nylon Polymers 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920002401 polyacrylamide Polymers 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920001230 polyarylate Polymers 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 229910052711 selenium Inorganic materials 0.000 description 2
- 239000011669 selenium Substances 0.000 description 2
- 238000012360 testing method Methods 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
- 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
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical group ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- 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 1
- WUPHOULIZUERAE-UHFFFAOYSA-N 3-(oxolan-2-yl)propanoic acid Chemical compound OC(=O)CCC1CCCO1 WUPHOULIZUERAE-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 229910000838 Al alloy Inorganic materials 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000207199 Citrus Species 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 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
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-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
- 239000002253 acid Substances 0.000 description 1
- 239000000980 acid dye 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
- 150000001408 amides Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052980 cadmium sulfide Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000012461 cellulose resin Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 238000007766 curtain coating Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229920006226 ethylene-acrylic acid Polymers 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 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
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000010147 laser engraving Methods 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 235000012149 noodles Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229920006287 phenoxy resin Polymers 0.000 description 1
- 239000013034 phenoxy resin Substances 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002717 polyvinylpyridine Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 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
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 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
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical class C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 1
- 238000007761 roller coating Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229960005265 selenium sulfide Drugs 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- PWEBUXCTKOWPCW-UHFFFAOYSA-N squaric acid Chemical compound OC1=C(O)C(=O)C1=O PWEBUXCTKOWPCW-UHFFFAOYSA-N 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Landscapes
- Photoreceptors In Electrophotography (AREA)
Abstract
Description
【発明の詳細な説明】
[産業上の利用分野J
本発明は、電子写真感光体に関し、詳しくは1荷発生層
と電荷輸送層を有する積層型の電子写真感光体に関する
。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application J] The present invention relates to an electrophotographic photoreceptor, and more particularly to a laminated electrophotographic photoreceptor having one charge generation layer and a charge transport layer.
[従来の技術]
従来、電子写真感光体としては、セレン、酸4力Fミウ
ム、酸化亜鉛などを主成分とする感光層を有する無機系
電子写真感光体が広く用いられてきた。これら無機電子
写真感光体は熱安定性、#A湿性、耐久性において必ず
しも満足し得ず、特にセレンおよび硫化カドミウムは毒
性のために製造上ならびに取扱い上に制約があった。[Prior Art] Conventionally, inorganic electrophotographic photoreceptors having a photosensitive layer mainly composed of selenium, acid tetrafluoride, zinc oxide, etc. have been widely used as electrophotographic photoreceptors. These inorganic electrophotographic photoreceptors are not necessarily satisfactory in terms of thermal stability, #A humidity, and durability, and in particular, selenium and cadmium sulfide have limitations in production and handling due to their toxicity.
一方、有機光導電性化合物を主成分とする感光層を有す
る′4#機電子写真感光体は、無機電子写真感光体の上
記欠点をおざなうなど多くの利点を有し、近年注目を集
めている。On the other hand, '4# electrophotographic photoreceptors, which have a photosensitive layer containing an organic photoconductive compound as a main component, have many advantages such as overcoming the above-mentioned disadvantages of inorganic electrophotographic photoreceptors, and have attracted attention in recent years. ing.
このような有機系感光体としては、ポリ−N−ビニルカ
ルバゾールに代表される光導電性ポリマーおよびこれと
2.4.7−)ジニトロ−9−2ルオレノンなどのルイ
ス酸とから形成される電荷移動錯体を主成分とする感光
層を有する電子写真感光体は既に実用化されている。Such organic photoreceptors include a photoconductive polymer typified by poly-N-vinylcarbazole and a charge formed from this and a Lewis acid such as 2.4.7-)dinitro-9-2-fluorenone. Electrophotographic photoreceptors having a photosensitive layer containing a transfer complex as a main component have already been put into practical use.
しかし、この電子写真感光体は感度および耐久性におい
て必ずしも満足できるものではない。However, this electrophotographic photoreceptor is not necessarily satisfactory in sensitivity and durability.
一方、電荷発生機能と電荷輸送機能とをそれぞれ別個の
物質に分担させた機能分離型電子写真感光体が、従来の
有機電子写真感光体の欠点とされていた感度や耐久性に
著しい改善をもたらした。On the other hand, functionally separated electrophotographic photoreceptors, in which the charge generation function and charge transport function are divided into separate substances, have brought about significant improvements in sensitivity and durability, which had been considered shortcomings of conventional organic electrophotographic photoreceptors. Ta.
このような機能分離型電子写真感光体は、電荷発生物質
、電荷輸送物質の各々の材料の材料選択範囲が広く、任
意の特性を有する電子写真感光体を比較的容易に製造し
得るという利点を有している。Such a functionally separated electrophotographic photoreceptor has the advantage that there is a wide selection range of materials for each of the charge-generating substance and the charge-transporting substance, and it is relatively easy to manufacture an electrophotographic photoreceptor with arbitrary characteristics. have.
特に電子写真感光体が複写機のみならず、近年ではレー
ザービームプリンター、LEDプリンターなどに用いら
れるようになるにつれ、使用する光源の発光波長に合っ
た分光感度域を設足するためには機能分離型が適してい
る。In particular, as electrophotographic photoreceptors have come to be used not only in copiers but also in laser beam printers, LED printers, etc. in recent years, functional separation is required to establish a spectral sensitivity range that matches the emission wavelength of the light source used. The type is suitable.
電荷発生物質としては種々のアゾ顔料、7タロシアニン
顔料、多環牛ノン顔料、シアニン色素、スクエアリック
酸染料、ピリリウム塩系色素などが知られている。As charge-generating substances, various azo pigments, heptalocyanine pigments, polycyclic bovine non-pigments, cyanine dyes, squaric acid dyes, pyrylium salt dyes, etc. are known.
中でもアゾ顔料は耐光性が強い、電荷発生能力が大きい
、材料合成が容易などの点から多くの構造が提唱されて
きた。Among them, many structures have been proposed for azo pigments because of their strong light resistance, large charge generation ability, and ease of material synthesis.
例えば本発明における電荷発生物質に類似のジスアゾ!
T4HトLテ特開昭56−116040号公輯、特開昭
57−182747号公報、特開昭58−49952号
公報、特開昭58−115447号公報、特開昭59−
72448号公報、特開昭59−155848号公報、
特開昭58−115445号公報、特開昭58−115
446号公報、特開昭59−7365号公輯などに記載
され公知である。For example, disazo which is similar to the charge generating substance in the present invention!
T4H To L Te JP-A-56-116040, JP-A-57-182747, JP-A-58-49952, JP-A-58-115447, JP-A-59-
Publication No. 72448, Japanese Unexamined Patent Publication No. 155848/1983,
JP-A-58-115445, JP-A-58-115
It is well known and is described in Japanese Patent Application Laid-open No. 446, Japanese Patent Application Laid-open No. 59-7365, and the like.
ここで電荷発生物質として用いられるアゾ顔料に要求さ
れることは、(i)熱、光に対して安定であること、(
ii )分散状態で電荷発生能を示すものでは1分数が
容易であることおよび分散液の経時変化の少ないこと、
(iii)ii電荷発生能温度により変化しないこと、
C5v)mり返し使用時において特性の変化のないこと
、CV)用いる光源に対して有効な分光感度域を有して
いること。The azo pigment used here as a charge generating substance is required to (i) be stable against heat and light;
ii) For those that exhibit charge generation ability in a dispersed state, it is easy to measure 1 fraction, and the dispersion liquid shows little change over time;
(iii) ii Charge generation ability does not change with temperature;
C5v) No change in characteristics when used repeatedly; CV) Must have an effective spectral sensitivity range for the light source used.
(vi )電荷輸送物質が限定されないことなどが挙げ
られる。(vi) The charge transport material is not limited.
これらの要求を高いレベルで平均的に満足することが実
用上最も重要なことである。Practically speaking, it is most important to satisfy these requirements at a high level on average.
前述の公知顔料の中には上記要求の一部は満足するもの
の、全てを高いレベルで満足するものはなかった。Although some of the above-mentioned known pigments satisfy some of the above requirements, none satisfy all of them to a high level.
さて、電荷輸送物質としてはヒドラゾン化合物ピラゾリ
ン化合物、スチルベン化合物、トリアリールメタン化合
物、アリールアミン化合物などが知られている。Now, as charge transport substances, hydrazone compounds, pyrazoline compounds, stilbene compounds, triarylmethane compounds, arylamine compounds, etc. are known.
これらの化合物に要求されることは、(i)光、熱に対
して安定であること、(ii )コロナ放電により発生
するオゾン、NOx、硝酸などに対して安定であること
、(iii )高い電荷輸送能を示すこと、(Iv)有
機溶剤、結着剤との相溶性が高いことなどが挙げられる
。These compounds are required to (i) be stable against light and heat, (ii) be stable against ozone, NOx, nitric acid, etc. generated by corona discharge, and (iii) have high Examples include exhibiting charge transport ability and (Iv) high compatibility with organic solvents and binders.
前述の公知アゾ顔料と電荷輸送物質との組合せの例とし
ては5例えば特開昭58−18636号公報、特開昭5
7−204551号公報、特開昭59−44050号公
報、特開昭59−44051号公報、特開昭59−15
7844号公報、特開昭60−24549号公報、特開
昭60−24550号公報、特開昭60−24551号
公報。Examples of combinations of the above-mentioned known azo pigments and charge transport substances include 5, for example, JP-A-58-18636;
7-204551, JP 59-44050, JP 59-44051, JP 59-15
7844, JP 60-24549, JP 60-24550, and JP 60-24551.
特開昭60−24552号公報などの記載が挙げられる
。Examples include the description in JP-A-60-24552.
これらの組合せによる電子写真感光体は繰り返し使用時
における電位変動は少ないものの使用環境の変化による
画像の劣化が見られるなど、画像特性上大きな欠点を有
しているものが多く、実際の使用上問題となっている。Although electrophotographic photoreceptors made with these combinations have little potential fluctuation during repeated use, many of them have major drawbacks in image characteristics, such as image deterioration due to changes in the usage environment, which poses problems in actual use. It becomes.
[発明が解決しようとする課題]
本発明の目的は、電荷発生層と電荷輸送層とを有する電
子写真感光体において、レーザーダイオード発振波長域
のような長波長域でも十分な高感度と分光感度のフラッ
トネスを有する電子写真感光体を提供すること、繰り返
し使用時の電位が安定に維持され、かつ、使用環境(温
度、湿度)によらず安定した電位特性と画像特性を示す
電子写真環状体を提供すること、アゾ顔料の分散が容易
で、しかも、分散液の経時変化の少ないアゾ顔料を用い
た電子写真感光体を提供することにある。[Problems to be Solved by the Invention] An object of the present invention is to provide an electrophotographic photoreceptor having a charge generation layer and a charge transport layer with sufficient high sensitivity and spectral sensitivity even in a long wavelength range such as the laser diode oscillation wavelength range. To provide an electrophotographic photoreceptor having a flatness of 1, and an electrophotographic annular body whose potential is maintained stably during repeated use, and which exhibits stable potential characteristics and image characteristics regardless of the usage environment (temperature, humidity). Another object of the present invention is to provide an electrophotographic photoreceptor using an azo pigment in which the azo pigment can be easily dispersed and the dispersion liquid has little change over time.
[課題を解決する手段1作用]
本発明は、導電性支持体上に電荷発生層と電荷輸送層を
有する電子写真感光体において、電荷発生層が電荷発生
物質として下記一般式(I)で示すジスアゾ顔料を含有
し、電荷輸送層が電荷輸送物質として下記一般式(II
)で示すビフェニル化合物を含有することを特徴とする
電子写真感光体から構成される。[Means for Solving the Problems 1 Effect] The present invention provides an electrophotographic photoreceptor having a charge generation layer and a charge transport layer on a conductive support, in which the charge generation layer is represented by the following general formula (I) as a charge generation substance. The charge transport layer contains a disazo pigment, and the charge transport layer has the following general formula (II
) is comprised of an electrophotographic photoreceptor characterized by containing a biphenyl compound shown in the following.
(式中、R1はフェニル基、0−トリル基、2−エチル
フェニル基、2.5−キシリル基、2.4−キシリル基
、2−メチル−5−二トロフェニル基、2−メチル−4
−メトキシフェニル基、2−エチル−5−ニトロフェニ
ル基および2−メチル−5−クロロフェニル基よりなる
群より選択される基を示し、Xはハロゲン原子を示す、
)一般式(II )
(式中、R2およびR3はアルキル基またはアルコキシ
基を示し、R4はアルキル基、アルコキシ基、アラルキ
ル基、水酸基または)\ロゲン原子を示す、)
さらに具体的には、上記基として、アルキル基はメチル
、エチル、プロピル、ブチルなどの基、アルコキシ基は
メトキシ、エトキシ、プロポキシなどの基、アラルキル
基はベンジル、フェネチルなどの基、ハロゲン原子は塩
素原子、臭素原子、フッ素原子、ヨウ素原子である。(In the formula, R1 is a phenyl group, 0-tolyl group, 2-ethylphenyl group, 2.5-xylyl group, 2.4-xylyl group, 2-methyl-5-nitrophenyl group, 2-methyl-4
- represents a group selected from the group consisting of methoxyphenyl group, 2-ethyl-5-nitrophenyl group, and 2-methyl-5-chlorophenyl group, and X represents a halogen atom,
) General formula (II) (In the formula, R2 and R3 represent an alkyl group or an alkoxy group, and R4 represents an alkyl group, an alkoxy group, an aralkyl group, a hydroxyl group, or a \rogen atom.) More specifically, the above As a group, alkyl groups include methyl, ethyl, propyl, and butyl, alkoxy groups include methoxy, ethoxy, and propoxy, aralkyl groups include benzyl and phenethyl, and halogen atoms include chlorine, bromine, and fluorine atoms. , is an iodine atom.
以下に本発明において用いられる電荷発生物質と電荷輸
送物質の代表例を挙げる。Typical examples of charge-generating substances and charge-transporting substances used in the present invention are listed below.
電荷発生物質
例示は基本型において変化する部分であるR1およびX
の具体例のみを記載することによる。Examples of charge generating substances include R1 and X, which are parts that vary in the basic form.
By describing only specific examples.
例示顔料 G−(1) R1:つ G−(2) R1ニー。Exemplary pigment G-(1) R1: one G-(2) R1 knee.
G−(3)
R1:噂
G−(4)
R1:べ◇
G−(5)
X :
X :
X :
X :
0文
r
■
G −
(6)
G−(7)
−
(8)
−
(9)
HJ
G−(10)
G−(11)
G−(12)
G−(13)
G−(14)
G−(15)
G−(16,)
G−(17)
G−(18)
CH)
G−(19)
C)+3
−
(20)
G−(21)
G−(22)
−
(23)
−
(24)
G−(25)
−
(26)
−
(27)
−
(28)
一
(29)
−
(30)
G−(31)
G −
(32)
−
(33)
−
(34)
l
−
(35)
−
(36)
H3
電荷輸送物質
例示化合物
−
(1)
一
(2)
−
(3)
一
(4)
−
(5)
−
(6)
−
(7)
−
(8)
−
(9)
T−(11)
T−(12)
−
(l 3)
一
(l 4)
T−(15)
−
(l 6)
−
(17)
−
(18)
T−(19)
T−
(20)
T−(21)
本発明における一般式(I)で示すジスアゾ顔料と一般
式(II )で示すビフェニル化合物の組み合せは、お
そらくイオン化ポテンシャルの適合または電荷発生物質
と電荷輸送物質の立体的重りが良いことなどの理由で、
電荷発生物質から電荷輸送物質への電荷の注入が良好に
行なわれるため、感度が良好で、残留電位も小さく、綴
り返し使用時の電位安定性にも優れるものと考えられる
。G-(3) R1: Rumor G-(4) R1: Be◇ G-(5) 9) HJ G-(10) G-(11) G-(12) G-(13) G-(14) G-(15) G-(16,) G-(17) G-(18) CH ) G-(19) C)+3-(20) G-(21) G-(22)-(23)-(24) G-(25)-(26)-(27)-(28) One( 29) - (30) G - (31) G - (32) - (33) - (34) l - (35) - (36) H3 Charge transport substance exemplified compound - (1) 1 (2) - (3 ) One (4) - (5) - (6) - (7) - (8) - (9) T-(11) T-(12) - (l 3) One (l 4) T-(15) - (l 6) - (17) - (18) T-(19) T- (20) T-(21) Disazo pigment represented by general formula (I) and biphenyl compound represented by general formula (II) in the present invention The combination of is probably due to the matching of ionization potential or the good steric weight of the charge-generating substance and the charge-transporting substance.
It is considered that since charge is well injected from the charge generating material to the charge transporting material, the sensitivity is good, the residual potential is small, and the potential stability when used for reversing is also excellent.
次に本発明の電子写真感光体について更に詳細に説明す
る。Next, the electrophotographic photoreceptor of the present invention will be explained in more detail.
電荷発生層は、十分な吸光度を得るために、できる限り
多くの一般式CI)で示すジスアゾ顔料を含有し、かつ
、発生した電荷キャリヤーの飛程を短くするために薄膜
層、例えば5μm以下、好ましくは0.01〜l、pm
の膜厚の薄膜層とすることが望ましい。The charge generation layer contains as much of the disazo pigment represented by the general formula CI) as possible in order to obtain sufficient absorbance, and is a thin film layer, for example, 5 μm or less, in order to shorten the range of the generated charge carriers. Preferably 0.01-1, pm
It is desirable to form a thin film layer with a thickness of .
電荷発生層は一般式(1)で示すジスアゾ顔料を通出な
バインダーに分散させ、これを導電性支持体上に塗工す
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ができる。The charge generation layer can be formed by dispersing the disazo pigment represented by the general formula (1) in a transparent binder and coating it on a conductive support, or by forming a vapor deposited film using a vacuum vapor deposition device. I can do it.
塗工によって形成する際に用いる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。As a binder used when forming by coating,
One can choose from a wide variety of insulating resins and organic photoconductive polymers such as poly-N-vinylcarbazole, polyvinylanthracene and polyvinylpyrene.
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とフタル酸の縮重合体なと)、ポリカー
ボネート、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、ポリアミド
、ポリビニルピリジン、セルロース系樹脂、ポリウレタ
ン、エポキシ柑脂、カゼイン、ポリビニルアルコール、
ポリビニルピロリドンなどが挙げられる。Preferably polyvinyl butyral, polyarylate (condensation polymer of bisphenol A and phthalic acid), polycarbonate, polyester, phenoxy resin, polyvinyl acetate, acrylic resin, polyacrylamide, polyamide, polyvinylpyridine, cellulose resin, polyurethane, epoxy Citrus fat, casein, polyvinyl alcohol,
Examples include polyvinylpyrrolidone.
電荷発生層中に含有する樹脂は80重量%以下好ましく
は40重量%以下が適している・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り、また電荷輸送層
や下引き層を溶解しない種類から選択することが好まし
い。The resin contained in the charge generation layer is preferably 80% by weight or less, preferably 40% by weight or less. The solvent that dissolves these resins varies depending on the type of resin, and does not dissolve the charge transport layer or undercoat layer. It is preferable to select from among the types.
具体的には、メタノール、エタノール、インプロパツー
ルなどのアルコール類、アセトン、メチルエチルケトン
、シクロヘキサノンなどのケトン類、N、N−ジメチル
ホルムアミド、N、N−ジメチルアセトアミドなどのア
ミド類、ジメチルスルホキシドなどのスルホキシド類、
テトラヒドロフラン、ジオキサン、エチレングリコール
モノメチルエーテルなどのエーテル類、酢酸メチル、酢
酸エチルなどのエステル類、クロロホルム、塩化メチレ
ン、ジクロルエチレン、四塩化炭素、トリクロロエチレ
ンなどの脂肪族ハロゲン化炭化水素あるいはベンゼン、
トルエン、キシレン、リグロイン、クロロベンゼン、ジ
クロロベンゼンなどの芳香族化合−物などを用いること
ができる。Specifically, alcohols such as methanol, ethanol, and impropatol, ketones such as acetone, methyl ethyl ketone, and cyclohexanone, amides such as N,N-dimethylformamide, N,N-dimethylacetamide, and sulfoxides such as dimethyl sulfoxide. kind,
Ethers such as tetrahydrofuran, dioxane, ethylene glycol monomethyl ether, esters such as methyl acetate, ethyl acetate, aliphatic halogenated hydrocarbons such as chloroform, methylene chloride, dichloroethylene, carbon tetrachloride, trichloroethylene, or benzene,
Aromatic compounds such as toluene, xylene, ligroin, chlorobenzene, dichlorobenzene, etc. can be used.
塗工方法としてはは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、マイヤーパーコーティング法、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
ング法などの塗工方法が採用できる。As the coating method, a dip coating method, a spray coating method, a spinner coating method, a bead coating method, a Mayer-Per coating method, a blade coating method, a roller coating method, a curtain coating method, and the like can be adopted.
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℃の温度範囲で5分〜
2時間の範囲で静止または送風下で行なう。Drying is preferably done by drying to the touch at room temperature and then heating. Drying by heating is performed at a temperature range of 30 to 200°C for 5 minutes or more.
Testing is carried out for 2 hours in a stationary or ventilated environment.
電荷輸送層は、電荷発生層と電気的に接続されており、
電界の存在下で電荷発生層から注入された電荷キャリヤ
ーを受は取るとともに、これらの電荷キャリヤーを表面
まで輸送できる機能を有している。この際、電荷輸送層
は電荷発生層の上に積層されていてもよく、またその下
に積層されていてもよい。The charge transport layer is electrically connected to the charge generation layer,
It has the function of receiving and taking charge carriers injected from the charge generation layer in the presence of an electric field and transporting these charge carriers to the surface. At this time, the charge transport layer may be laminated on or under the charge generation layer.
電荷輸送層は、−形成(II )で示すビフェニル化合
物を適当なバインダーと共に溶解し、これを塗布して形
成される。The charge transport layer is formed by dissolving the biphenyl compound represented by (II) together with a suitable binder and applying the solution.
バインダーとしては1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−スチレンコポリマー、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、
ポリスルホルマル、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ポリマーなどが
挙げられる。Examples of the binder include acrylic resin, polyarylate, polyester, polycarbonate polystyrene,
Acrylonitrile-styrene copolymer, acrylonitrile-butadiene copolymer, polyvinyl butyral,
Examples include insulating resins such as polysulfal formal, polysulfone, polyacrylamide, polyamide, and chlorinated rubber, and organic photoconductive polymers such as poly-N-vinylcarbazole, polyvinylanthracene, and polyvinylpyrene.
電荷輸送層は電荷キャリヤー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はできない、一般的
には5〜35gmであるが、好ましい範囲は8〜30#
Lmである。Since the charge transport layer has a limit in its ability to transport charge carriers, it cannot be made thicker than necessary. Generally, the thickness is 5 to 35 gm, but the preferred range is 8 to 30 gm.
It is Lm.
塗工によって電荷輸送層を形成する際には、前述したよ
うな適当な塗工方法を採用できる。When forming the charge transport layer by coating, any suitable coating method as described above can be employed.
このような電荷発生層と電荷輸送層の積層構造からなる
電子写真感光体は、導電層を有する支持体上に設けられ
る。An electrophotographic photoreceptor having such a laminated structure of a charge generation layer and a charge transport layer is provided on a support having a conductive layer.
導を暦査有する支持体としては支持体自体が導電性を有
するもの1例えばアルミニウム、アルミこラム合金など
の金属や合金を用いることができる。As the support having electrical conductivity, it is possible to use a material whose support itself is electrically conductive, such as a metal or alloy such as aluminum or aluminum column alloy.
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、酸化スズ、酸化インジウム−酸化スズ合金などを
真空蒸着法によって塗膜形成された暦を有するプラスチ
ック、導電性粒子(例えばカーボンブラック、銀粒子な
ど)を適当なバインダーとともにプラスチックヤ前記金
属支持体の上に被覆した導電性支持体、導電性粒子をプ
ラスチックや紙に含浸した導電性支持体や導電性ポリマ
ーを有するプラスチックなどが挙げられる。In addition, plastics having a coating film formed by vacuum evaporation of aluminum, aluminum alloy, indium oxide, tin oxide, indium oxide-tin oxide alloy, etc., and conductive particles (e.g. carbon black, silver particles, etc.) may be used as appropriate. Examples include a conductive support in which a plastic material is coated on the metal support together with a binder, a conductive support in which plastic or paper is impregnated with conductive particles, and a plastic containing a conductive polymer.
導電性支持体と感光層の中間に、へリヤー機能と接着機
能を有する下引き層を設けることもできる。An undercoat layer having a healer function and an adhesive function can also be provided between the conductive support and the photosensitive layer.
下引キ層はカゼイン、ポリビニルアルコール。The undercoat layer is casein and polyvinyl alcohol.
ニトロセルロース、エチレン−アクリル酸コホl)マー
、ポリアミド(ナイロン6、ナイロン66、ナイロン6
10.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、ゼラチン醇化アルミニウムなどに
よって形成できる。Nitrocellulose, ethylene-acrylic acid coformer, polyamide (nylon 6, nylon 66, nylon 6)
10. It can be formed from copolymerized nylon, alkoxymethylated nylon, etc.), polyurethane, gelatin-melted aluminum, etc.
下引き層の膜厚は0.1〜5gm、好ましくは05〜3
μmが適当である。The thickness of the undercoat layer is 0.1 to 5 gm, preferably 0.5 to 3 gm.
μm is appropriate.
本発明の電子写真感光体はレーザーダイオード7゛リン
ターに用いることで性能を十分に生かすことができ、ま
た、LEDプリンター、a晶プリンター、レーザー製版
などの電子写真応用分野にも広く利用できる。The electrophotographic photoreceptor of the present invention can be used in a laser diode 7' printer to fully utilize its performance, and can also be widely used in electrophotographic applications such as LED printers, a-crystalline printers, and laser engraving.
[実施例]
実施例1
アルミ板上に0.1pmの塩化ビニル−無水マレイン酸
−酢酸ビニルコポリマーを用いた下引き層を形成した。[Examples] Example 1 An undercoat layer using a 0.1 pm vinyl chloride-maleic anhydride-vinyl acetate copolymer was formed on an aluminum plate.
次に1例示顔月G−(26)の5gをシクロヘキサノ〉
′95 m lにブチラール樹脂(ブチラール化度63
モル%、数平均分子量2万)2gを溶かした液に加えサ
ンドミルで20時間分散した。Next, add 5 g of one example of Kao-zuki G-(26) to cyclohexano
'95 ml of butyral resin (butyralization degree 63
2 g (mol%, number average molecular weight: 20,000) was added to the solution and dispersed in a sand mill for 20 hours.
この分散液を下引き暦の上に乾燥後の膜厚が0.4.p
mとなるようにマイヤーパー塗布し、乾燥して電荷発生
層を形成した。The film thickness after drying this dispersion was applied to a base plate of 0.4. p
A charge generating layer was formed by applying Mayer per coat to give a thickness of m and drying.
次に、例示ビフェニル化合物T−(1)を5gとビスフ
ェノールZ型子リカーボネート(粘度平均分子量3万)
5gをクロロベンゼン70m1に溶解し、これを電荷発
生層の上に乾燥後の膜厚が17=mとなるようにマイヤ
ーパー塗布し、乾燥して電荷輸送層を形成した。Next, 5 g of exemplified biphenyl compound T-(1) and bisphenol Z-type colicarbonate (viscosity average molecular weight 30,000) were added.
5 g of the solution was dissolved in 70 ml of chlorobenzene, and Mayer Per coating was applied onto the charge generation layer so that the film thickness after drying was 17 m, followed by drying to form a charge transport layer.
製造した電子写真感光体を感光体lとする。The produced electrophotographic photoreceptor is referred to as photoreceptor 1.
感光体lt−静電複写紙試験装置ModelSP−42
8(用口電1!麹製)を用いてスタチック方式で−5,
5KVのコロナ帯電し、暗所で1秒間保持した後、照度
2ルツクスのハロゲンランプで露光し、帯電特性を測定
した。Photoreceptor lt-electrostatic copying paper testing device ModelSP-42
-5 by static method using 8 (Using mouthpiece 1! made by Koji),
After corona charging at 5 KV and holding for 1 second in a dark place, the sample was exposed to light using a halogen lamp with an illuminance of 2 lux, and the charging characteristics were measured.
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(VD )を1/6に減衰するに必要な露
光量(El/6)を測定した。As for charging characteristics, the surface potential (Vo) and the exposure amount (El/6) required to attenuate the potential (VD) to 1/6 when dark decayed for 1 second were measured.
結果を示す。Show the results.
VOニー710V
v、、ニー702V
El/6:1.56iuxesec
さらに感光体lを−5,6KVのコロナ帯電器、露光光
学系、現像器、転写帯電器、除!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
、画像特性を調べた。VO Knee 710V v,, Knee 702V El/6: 1.56 iuxesec In addition, remove the photoreceptor l from the -5.6KV corona charger, exposure optical system, developer, transfer charger! It was attached to the cylinder of an electrophotographic copying machine equipped with an exposure optical system and a cleaner, and image characteristics were investigated.
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。This copying machine is configured to produce an image on transfer paper as a cylinder is driven.
画像評価は、湿度10%、気温5℃、湿度50%、気温
18°C,湿度80%、気温35°Cの三環境において
それぞれ行なった。Image evaluation was performed in three environments: 10% humidity, 5°C air temperature, 50% humidity, 18°C air temperature, 80% humidity, and 35°C air temperature.
いずれの環境においてもオリジナルに忠実な良好な画像
が得られた。この画像は1万枚目においても画像の滲み
、ボケなどは見られず、感光体1が良好な画像特性を示
すことが分った。Good images faithful to the original were obtained in both environments. No blurring or blurring of the image was observed even after the 10,000th copy, indicating that photoreceptor 1 exhibited good image characteristics.
感光体1のレーザー発振波長域である770〜800n
mにかけての感度変化
+1+(’/’/Llnm)
ΔE−0,97と極めて小さいことが分った。770-800n which is the laser oscillation wavelength range of the photoreceptor 1
It was found that the sensitivity change over m was +1+('/'/Llnm) ΔE-0.97, which was extremely small.
比較例1〜3
特開昭62−147463号公報に記載の下記比較顔料
(1)、(2)および(3)を用いた以外は実施例1と
全く同様にして電子写真感光体を製造した。それぞれ、
比較感光体1.2および3とする。Comparative Examples 1 to 3 Electrophotographic photoreceptors were produced in exactly the same manner as in Example 1, except that the following comparative pigments (1), (2), and (3) described in JP-A-62-147463 were used. . Each,
Comparative photoreceptors 1.2 and 3.
比較顔料(1)
比較顔料
(2)
比較顔#(3)
実施例1の場合と同様にして、比較感光体1.2および
3について帯電特性を調べた。Comparative Pigment (1) Comparative Pigment (2) Comparative Face #(3) In the same manner as in Example 1, the charging characteristics of Comparative Photoreceptors 1.2 and 3 were investigated.
さらに760〜800nmにかけての感度変化ΔEを計
算した。結果を示す。Furthermore, the sensitivity change ΔE from 760 to 800 nm was calculated. Show the results.
(1) 630 609 4.5 0.81
(2) 650 629 4.0 0.77(
3) 670 641 7.1 0.62以上
の結果から、本発明の電子写真感光体1士高感度でレー
ザーダイオード発振波長域でフラー/ )な分光感度を
示すことが分った。(1) 630 609 4.5 0.81
(2) 650 629 4.0 0.77 (
3) From the results of 670 641 7.1 0.62, it was found that the electrophotographic photoreceptor of the present invention exhibits high sensitivity and full spectral sensitivity in the laser diode oscillation wavelength range.
実施例1中、電子写真複写機における暗部電位(Vo
)を−700Vに設定し、760nmにおいて明部電位
(VL )が−200Vになるようにレーザーダイオー
ドの光量を設定したときの同一光量の800nmにおけ
る表面電位は以下のようになり、本発明の電子写真感光
体はレーザー発振波長が変化してもコントラスト電位の
変動が少なく、画像特性上極めて優れた電子写真感光体
であることが分かる。In Example 1, the dark potential (Vo
) is set to -700V, and the light intensity of the laser diode is set so that the bright area potential (VL) is -200V at 760nm, the surface potential at 800nm with the same light intensity is as follows, and the electron of the present invention It can be seen that the photographic photoreceptor exhibits little variation in contrast potential even when the laser oscillation wavelength changes, and is an electrophotographic photoreceptor with extremely excellent image characteristics.
感光体I
VL (800nm) : −204V比較感光体I
VL (800nm) : −315V比較感光体2
VL (800nm) : −351V比較感光体3
VL (800nm) : −450V実施例2〜4
3
例示顔料と例示ビフェニル化合物を組合せ実施例1と同
様にして電子写真感光体を製造し、露光iE1/6を測
定した。Photoreceptor IVL (800nm): -204V Comparative photoreceptor IVL (800nm): -315V Comparative photoreceptor 2 VL (800nm): -351V Comparative photoreceptor 3 VL (800nm): -450V Examples 2 to 4
3 An electrophotographic photoreceptor was produced in the same manner as in Example 1 by combining the exemplified pigment and the exemplified biphenyl compound, and the exposure iE1/6 was measured.
そしてコロナ帯電器、露光光学系、現像器、転写帯電器
、除41t、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。Then, it was attached to the cylinder of an electrophotographic copying machine equipped with a corona charger, an exposure optical system, a developing device, a transfer charger, a 41t, an exposure optical system, and a cleaner.
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。This copying machine is configured to produce an image on transfer paper as a cylinder is driven.
この複写機を用いて初期の明部電位(VL )と暗部電
位(Vp )をそれぞれ−200v、−700vに設足
し、1万回使用した後の明部電位と暗部電位の変動量Δ
VLとΔVOを測定した。Using this copying machine, the initial bright area potential (VL) and dark area potential (Vp) were set to -200v and -700v, respectively, and the amount of variation Δ in the bright area potential and dark area potential after 10,000 times of use.
VL and ΔVO were measured.
結果を示す。Show the results.
例示顔料と例示ビフェニル化合物との組合せ成
−ビフ ニル
2 2 G−(1) T−(1)
3 3 G−(1) T−(9)4
4 G−(2) T−(1)5
5 G−(2) T−(9)0
1
2
3
4
5
6
7
8
工9
0
1
2
3
4
5
0
1
工2
3
4
5
6
7
8
9
0
1
2
3
4
5
G−(3)
G−(4)
G−(5)
G−(6)
G−(6)
G−(7)
G−(9)
G−(10)
G−(10)
G−(11)
G−(11)
G−(12)
G−(13)
G−(14)
G−(14)
G−(17)
G−(17)
G−(18)
G−(18)
G−(19)
T−(2)
T−(2)
T−(15)
T−(5)
T−(3)
T−(6)
T−(3)
T−(14)
T−(9)
T−(1)
T−(11)
T−(12)
T−(13)
T−(1)
T−(15)
T−(1)
T−(16)
T−(2)
T−(3)
T−(6)
6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
1
2
3
6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
1
9
0
G−(19)
G−(20)
G−(21)
G−(22)
G−(23)
G−(25)
G−(25)
G−(26)
G−(26)
G−(27)
G−(27)
G−(28)
G−(29)
G−(30)
G−(30)
G−(31)
G −(33)
G−(35)
T−(9)
T−(11)
T−(4)
T−(17)
T−(18)
T−(19)
T−(1)
T−(2)
T−(19)
T−(4)
T−(20)
T−(21)
T−(13)
T−(5)
T−(15)
T−(14)
T−(16)
T−(6)
0
1
2
3
4
5
6
7
8
9
0
1
i、si
1 、81
1 、61
2 、41
1 、60
1 、51
1 、95
1.70
2、 10
2 、05
2 、 l 9
1 、71
2 、41
1 、69
2 、49
2 、00
2、 10
1.60
1.90
1 、75
4
14
7
11
6
7
2〇
4
= 14
16
17
9
12
8
13
15
16
11
= 6
3
〜11
2
12
7
4
11
7
14
15
11
8
19
6
18
17
14
5
14
5
2
23
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
1
エ 、 90
1.80
2 、24
2 、00
2、 10
2 、49
1 、69
1 、95
1 、99
2 、75
1 、60
1 、70
2 、49
1 、81
2 、70
2 、80
2 、89
1 、64
1 、96
1 、60
18
4
15
15
14
16
2
17
10
10
4
7
16
6
15
13
14
7
= 14
11
14
6
18
18
10
11
= 1
18
17
16
9
7
17
4
14
14
17
6
18
18
42 2.01 −19 −174
3 1.98 −5 −2
比較例4〜6
比較感光体l、2および3を用いて実施例2と同様にし
てΔVDとΔVLを測定した。結果を示す。Combination composition of exemplified pigment and exemplified biphenyl compound
-Bifnyl 2 2 G-(1) T-(1)
3 3 G-(1) T-(9)4
4 G-(2) T-(1)5
5 G-(2) T-(9) 0 1 2 3 4 5 6 7 8 Engineering 9 0 1 2 3 4 5 0 1 Engineering 2 3 4 5 6 7 8 9 0 1 2 3 4 5 G-(3) G-(4) G-(5) G-(6) G-(6) G-(7) G-(9) G-(10) G-(10) G-(11) G-(11) G-(12) G-(13) G-(14) G-(14) G-(17) G-(17) G-(18) G-(18) G-(19) T-(2) T-(2) T-(15) T-(5) T-(3) T-(6) T-(3) T-(14) T-(9) T-(1) T-(11) T-(12) T-(13) T-(1) T-(15) T-(1) T-(16) T-(2) T-(3) T-(6) 6 7 8 9 0 1 2 3 4 5 6 7 8 9 0 1 2 3 6 7 8 9 0 1 2 3 4 5 6 7 8 9 0 1 9 0 G-(19) G-(20) G-(21) G-(22 ) G-(23) G-(25) G-(25) G-(26) G-(26) G-(27) G-(27) G-(28) G-(29) G-(30 ) G-(30) G-(31) G-(33) G-(35) T-(9) T-(11) T-(4) T-(17) T-(18) T-(19 ) T-(1) T-(2) T-(19) T-(4) T-(20) T-(21) T-(13) T-(5) T-(15) T-(14 ) T-(16) T-(6) 0 1 2 3 4 5 6 7 8 9 0 1 i, si 1 , 81 1 , 61 2 , 41 1 , 60 1 , 51 1 , 95 1.70 2, 10 2 , 05 2 , l 9 1 , 71 2 , 41 1 , 69 2 , 49 2 , 00 2 , 10 1.60 1.90 1 , 75 4 14 7 11 6 7 20 4 = 14 16 17 9 12 8 13 15 16 11 = 6 3 ~ 11 2 12 7 4 11 7 14 15 11 8 19 6 18 17 14 5 14 5 2 23 4 5 6 7 8 9 0 1 2 3 4 5 6 7 8 9 0 1 E, 90 1.80 2 , 24 2 , 00 2 , 10 2 , 49 1 , 69 1 , 95 1 , 99 2 , 75 1 , 60 1 , 70 2 , 49 1 , 81 2 , 70 2 , 80 2 , 89 1 , 64 1 , 96 1 , 60 18 4 15 15 14 16 2 17 10 10 4 7 16 6 15 13 14 7 = 14 11 14 6 18 18 10 11 = 1 18 17 16 9 7 17 4 14 14 17 6 18 18 42 2.01 -19 -174
3 1.98 -5 -2
Comparative Examples 4 to 6 ΔVD and ΔVL were measured in the same manner as in Example 2 using comparative photoreceptors 1, 2, and 3. Show the results.
4 1 −51
−405 2 −39
−156 3 −31
−21上記の結果から、本発明の電子写真
感光体は。4 1 -51
-405 2 -39
-156 3 -31
-21 From the above results, the electrophotographic photoreceptor of the present invention.
繰り返し使用時の電位の変動が小さいことが分かる。It can be seen that the fluctuation in potential during repeated use is small.
比較例7〜11 実施例1におけるビフェニル化合物に代えて。Comparative Examples 7 to 11 In place of the biphenyl compound in Example 1.
下記構造式の化合物H−(1)、H−(2)、H−(3
)、H−(4)およびH−(5)の化合物を電荷輸送物
質として用いた他は、実施例1と全く同様にして電子写
真感光体を製造し、それぞれ比較感光体4,5.6.7
および8とし、帯電特性を測定した。Compounds H-(1), H-(2), H-(3
), H-(4), and H-(5) were used as the charge transport materials, electrophotographic photoreceptors were produced in exactly the same manner as in Example 1, and comparative photoreceptors 4, 5.6, and 5.6 were produced, respectively. .7
and 8, and the charging characteristics were measured.
また実施例2と全く同様にして電位変動量を測定した。Further, the amount of potential fluctuation was measured in exactly the same manner as in Example 2.
結果を示す。Show the results.
H−(1) H−(2) −
(3)
−
(4)
H−(5)
98
30
00
92
99
57
87
80
54
71
2.5
2.7
4.8
2.9
3 、8
威 Δv v ΔVL V7
4 −38 −358
5 −28 +IO
96−10−85
107−35+20
11 8 −50 −
69比較例12〜25
上記電荷輸送物質H−(1)、H−(2)、H−(3)
、H−(4)、H−(5)と実施例6゜9.15.35
.41で用いた電荷発生物質を以下のように組合せ、実
施例1と同様にして比較感光体9〜22を製造し、帯電
特性と電位変動量を測定した。結果を示す。H-(1) H-(2) - (3) - (4) H-(5) 98 30 00 92 99 57 87 80 54 71 2.5 2.7 4.8 2.9 3, 8 Power Δv v ΔVL V7
4 -38 -358
5 -28 +IO
96-10-85 107-35+20 11 8 -50 -
69 Comparative Examples 12 to 25 The above charge transport materials H-(1), H-(2), H-(3)
, H-(4), H-(5) and Example 6゜9.15.35
.. Comparative photoreceptors 9 to 22 were manufactured in the same manner as in Example 1 by combining the charge generating substances used in Example 41 as shown below, and the charging characteristics and potential fluctuation amount were measured. Show the results.
威
12 9 G−(3) H−(1)13
10 G−(3) H−(3)14 11
G−(3) H−(5)15 12
G−(6) H−(2)16 13’ G−
(6) H−(4)17 14 G−(6)
H−(5) 8
19
0
1
2
3
4
5
5
工6
7
8
9
0
1
2
G−(l 1)
G−(11)
G−(11)
G−(27)
G−(27)
G−(27)
G−(31)
G−(31)
H−(2)
H−(3)
H−(4)
H−(1)
H−(3)
H−(5)
H−(2)
H−(3)
2
3
4
5
6
7
8
9
0
1
2
2 、4
4 、7
4.0
2 、4
2.1
3 、4
2.5
3.7
2.0
2.5
3 、8
49
=78
40
34
40
70
42
49
37
60
61
9
−104
80
+30
+IO
81
+15
84
+15
50
0
23 4.0 −54 −7024
2.5 −60 +4025
3.9 −34 −98以上の結果
から、本発明の電子写真感光体は。Wei 12 9 G-(3) H-(1) 13
10 G-(3) H-(3)14 11
G-(3) H-(5) 15 12
G-(6) H-(2)16 13' G-
(6) H-(4) 17 14 G-(6)
H-(5) 8 19 0 1 2 3 4 5 5 Engineering 6 7 8 9 0 1 2 G-(l 1) G-(11) G-(11) G-(27) G-(27) G- (27) G-(31) G-(31) H-(2) H-(3) H-(4) H-(1) H-(3) H-(5) H-(2) H- (3) 2 3 4 5 6 7 8 9 0 1 2 2 , 4 4 , 7 4.0 2 , 4 2.1 3 , 4 2.5 3.7 2.0 2.5 3 , 8 49 = 78 40 34 40 70 42 49 37 60 61 9 -104 80 +30 +IO 81 +15 84 +15 50 0 23 4.0 -54 -7024
2.5 -60 +4025
3.9 -34 -98 From the above results, the electrophotographic photoreceptor of the present invention.
感度および繰り返し特性において優れていることが分か
る。It can be seen that the sensitivity and repeatability are excellent.
実麺例44〜48
本発明の電子写真感光体である感光体6,719.21
および35を120ppmのオゾン中に30分間暴露し
、さらにaoppmのHNO3ガス中に1時間暴露した
後、実施何重と全く同様にして帯電特性を測定した。結
果を示す。Actual Noodle Examples 44-48 Photoreceptor 6,719.21 which is an electrophotographic photoreceptor of the present invention
and 35 were exposed to 120 ppm ozone for 30 minutes and further exposed to aoppm HNO3 gas for 1 hour, and then the charging characteristics were measured in exactly the same manner as in the experiment. Show the results.
44 6 704 699 1.71
45 7 700 694 1.79
46 19 709 700 1.58
47 21 701 681 1.514
8 35 710 700 1.81比較
例26〜30
比較感光体3.10.12.21および23を用いて実
施例44と同様にして帯電特性を測定した。結果を示す
。44 6 704 699 1.71
45 7 700 694 1.79
46 19 709 700 1.58
47 21 701 681 1.514
8 35 710 700 1.81 Comparative Examples 26 to 30 Charging characteristics were measured in the same manner as in Example 44 using Comparative Photoreceptors 3.10.12.21 and 23. Show the results.
26 3 640 530 3.
627 10 610 560 3.1
28 12 600 550 4.92
9 21 610 500 4.73
0 23 640 570 4.4上
記の結果から、本発明の電子写真感光体は。26 3 640 530 3.
627 10 610 560 3.1
28 12 600 550 4.92
9 21 610 500 4.73
0 23 640 570 4.4 From the above results, the electrophotographic photoreceptor of the present invention.
オゾンや硝酸などのコロナ帯電による酸化性物質に対し
極めて安定した感光体であることが分る。It is found that the photoreceptor is extremely stable against oxidizing substances caused by corona charging, such as ozone and nitric acid.
[発明の効果]
本発明の電子写真感光体は、特定の電荷発生物質と特定
の電荷輸送物質を組合せることにより。[Effects of the Invention] The electrophotographic photoreceptor of the present invention is produced by combining a specific charge-generating substance and a specific charge-transporting substance.
■レーザーダイオードの発振波長域で高感度かつフラッ
トな分光特性を有し、■電子写真プロセスにおける安定
した画像特性を示し、■電位安定性に優れているという
顕著な効果を奏する。It has the remarkable effects of: (1) high sensitivity and flat spectral characteristics in the oscillation wavelength range of a laser diode, (2) stable image characteristics in the electrophotographic process, and (2) excellent potential stability.
Claims (1)
電子写真感光体において、電荷発生層が電荷発生物質と
して下記一般式( I )で示すジスアゾ顔料の少なくと
も一種を含有する層から成り、電荷輸送層が電荷輸送物
質として下記一般式(II)で示すビフェニル化合物の少
なくとも一種を含有する層から成ることを特徴とする電
子写真感光体。 一般式( I ) ▲数式、化学式、表等があります▼ (式中、R_1はフェニル基、o−トリル基、2−エチ
ルフェニル基、2、5−キシリル基、2、4−キシリル
基、2−メチル−5−ニトロフェニル基、2−メチル−
4−メトキシフェニル基、2−エチル−5−ニトロフェ
ニル基および2−メチル−5−クロロフェニル基よりな
る群より選択される基を示し、Xはハロゲン原子を示す
。) 一般式(II) ▲数式、化学式、表等があります▼ (式中、R_2およびR_3はアルキル基またはアルコ
キシ基を示し、R_4はアルキル基、アルコキシ基、ア
ラルキル基、水酸基またはハロゲン原子を示す。) 2、電荷輸送層が電荷輸送物質として下記一般式(III
)で示すビフェニル化合物の少なくとも一種を含有する
層からなる請求項1記載の電子写真感光体。 一般式(III) ▲数式、化学式、表等があります▼ (式中、R_5、R_6およびR_7はアルキル基また
はアルコキシ基を示す。)[Scope of Claims] 1. In an electrophotographic photoreceptor having a charge generation layer and a charge transport layer on a conductive support, the charge generation layer contains at least one disazo pigment represented by the following general formula (I) as a charge generation substance. 1. An electrophotographic photoreceptor comprising a layer containing at least one biphenyl compound represented by the following general formula (II) as a charge transporting substance. General formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, R_1 is a phenyl group, o-tolyl group, 2-ethylphenyl group, 2,5-xylyl group, 2,4-xylyl group, 2 -Methyl-5-nitrophenyl group, 2-methyl-
It represents a group selected from the group consisting of 4-methoxyphenyl group, 2-ethyl-5-nitrophenyl group and 2-methyl-5-chlorophenyl group, and X represents a halogen atom. ) General formula (II) ▲There are numerical formulas, chemical formulas, tables, etc.▼ (In the formula, R_2 and R_3 represent an alkyl group or an alkoxy group, and R_4 represents an alkyl group, an alkoxy group, an aralkyl group, a hydroxyl group, or a halogen atom. ) 2. The charge transport layer has the following general formula (III
2. The electrophotographic photoreceptor according to claim 1, comprising a layer containing at least one of the biphenyl compounds represented by the following. General formula (III) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, R_5, R_6 and R_7 represent an alkyl group or an alkoxy group.)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP641190A JPH03211559A (en) | 1990-01-17 | 1990-01-17 | Electrophotographic sensitive body |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP641190A JPH03211559A (en) | 1990-01-17 | 1990-01-17 | Electrophotographic sensitive body |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH03211559A true JPH03211559A (en) | 1991-09-17 |
Family
ID=11637627
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP641190A Pending JPH03211559A (en) | 1990-01-17 | 1990-01-17 | Electrophotographic sensitive body |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH03211559A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1018672A1 (en) * | 1999-01-08 | 2000-07-12 | Canon Kabushiki Kaisha | Process for producing electrophotographic photosensitive member |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH01183663A (en) * | 1988-01-14 | 1989-07-21 | Canon Inc | Electrophotographic sensitive body |
JPH01280763A (en) * | 1987-10-20 | 1989-11-10 | Ricoh Co Ltd | Electrophotographic sensitive body |
-
1990
- 1990-01-17 JP JP641190A patent/JPH03211559A/en active Pending
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH01280763A (en) * | 1987-10-20 | 1989-11-10 | Ricoh Co Ltd | Electrophotographic sensitive body |
JPH01183663A (en) * | 1988-01-14 | 1989-07-21 | Canon Inc | Electrophotographic sensitive body |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1018672A1 (en) * | 1999-01-08 | 2000-07-12 | Canon Kabushiki Kaisha | Process for producing electrophotographic photosensitive member |
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