JPH0358054A - Electrophotographic sensitive body - Google Patents
Electrophotographic sensitive bodyInfo
- Publication number
- JPH0358054A JPH0358054A JP19456389A JP19456389A JPH0358054A JP H0358054 A JPH0358054 A JP H0358054A JP 19456389 A JP19456389 A JP 19456389A JP 19456389 A JP19456389 A JP 19456389A JP H0358054 A JPH0358054 A JP H0358054A
- Authority
- JP
- Japan
- Prior art keywords
- photosensitive layer
- groups
- photoreceptor
- layer
- substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 229920000642 polymer Polymers 0.000 claims abstract description 18
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical compound C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 12
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
- -1 methylenedioxy groups Chemical group 0.000 claims description 39
- 108091008695 photoreceptors Proteins 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 239000000758 substrate Substances 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 2
- 230000005496 eutectics Effects 0.000 abstract description 28
- 230000035945 sensitivity Effects 0.000 abstract description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 5
- 239000004417 polycarbonate Substances 0.000 abstract description 4
- 229920000515 polycarbonate Polymers 0.000 abstract description 4
- 125000000547 substituted alkyl group Chemical group 0.000 abstract description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 abstract 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 54
- 229920005989 resin Polymers 0.000 description 12
- 239000011347 resin Substances 0.000 description 12
- 238000000576 coating method Methods 0.000 description 11
- 239000000975 dye Substances 0.000 description 11
- 239000011248 coating agent Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000002131 composite material Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000011230 binding agent Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 239000011241 protective layer Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 239000004014 plasticizer Substances 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 125000003107 substituted aryl group Chemical group 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 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
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical group O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 2
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical group [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 239000007822 coupling agent Substances 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 239000011147 inorganic material Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Chemical group 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 229920006324 polyoxymethylene Polymers 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 239000004800 polyvinyl chloride Substances 0.000 description 2
- 229920000915 polyvinyl chloride Polymers 0.000 description 2
- 239000005033 polyvinylidene chloride Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910052711 selenium Chemical group 0.000 description 2
- 229920002050 silicone resin Polymers 0.000 description 2
- 238000004544 sputter deposition Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- 229910001887 tin oxide Inorganic materials 0.000 description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound 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
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 1
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- LCHYEKKJCUJAKN-UHFFFAOYSA-N 2-propylphenol Chemical compound CCCC1=CC=CC=C1O LCHYEKKJCUJAKN-UHFFFAOYSA-N 0.000 description 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229910000838 Al alloy Inorganic materials 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000004709 Chlorinated polyethylene Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- MXSORXOBAXRPQY-UHFFFAOYSA-N Cl(=O)(=O)O.Cl(=O)(=O)(=O)O.Cl(=O)(=O)O Chemical compound Cl(=O)(=O)O.Cl(=O)(=O)(=O)O.Cl(=O)(=O)O MXSORXOBAXRPQY-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 229920006257 Heat-shrinkable film Polymers 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 244000218514 Opuntia robusta Species 0.000 description 1
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- 239000004642 Polyimide Substances 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 239000011354 acetal resin Substances 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
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- 125000001118 alkylidene group Chemical group 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 238000002048 anodisation reaction Methods 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
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000012461 cellulose resin Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
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- 229910052802 copper Inorganic materials 0.000 description 1
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- 150000001924 cycloalkanes Chemical class 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 1
- NJLLQSBAHIKGKF-UHFFFAOYSA-N dipotassium dioxido(oxo)titanium Chemical compound [K+].[K+].[O-][Ti]([O-])=O NJLLQSBAHIKGKF-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 125000005059 halophenyl group Chemical group 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
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- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
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- 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
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
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- 238000002791 soaking Methods 0.000 description 1
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- 239000010935 stainless steel Substances 0.000 description 1
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- 125000005504 styryl group Chemical group 0.000 description 1
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- WRTMQOHKMFDUKX-UHFFFAOYSA-N triiodide Chemical compound I[I-]I WRTMQOHKMFDUKX-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Landscapes
- Photoreceptors In Electrophotography (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
〔技術分野〕
本発明は，電子写真感光体に関し、詳しくは、共晶錯体
感光層中に特定の構造を有する物質を添加した電子写真
感光体及び前記感光層（第１感光層）を他の第２感光層
と積層してなる電子写真用複合感光体（２色プロセス用
）に関する。DETAILED DESCRIPTION OF THE INVENTION [Technical Field] The present invention relates to an electrophotographic photoreceptor, and more particularly, to an electrophotographic photoreceptor in which a substance having a specific structure is added to a eutectic complex photoreceptor layer, and an electrophotographic photoreceptor in which a substance having a specific structure is added to the photoreceptor layer (the first photoreceptor layer). The present invention relates to a composite photoreceptor for electrophotography (for two-color process) formed by laminating a first photosensitive layer and a second photosensitive layer.
ピリリウム系染料と電気１＃＠林性重合体とからなる共
晶錯体及び必要あればトリフェニルメタン系増感剤を加
えた組成物を光導電層とした電子写真用感光体は公知で
ある（例えば特公昭４６−２２５１８号公報、同４６−
２２５１９号公報，同５１−１１２９号公報、特開昭４
７−１０７８５号公報，同５１−８８２２６号公報、同
５１−９３３２４号公報、同５３−８７２２７号公報等
）。Electrophotographic photoreceptors having a photoconductive layer made of a composition containing a eutectic complex consisting of a pyrylium dye and a Denki 1# polymer and, if necessary, a triphenylmethane sensitizer, are known ( For example, Japanese Patent Publication No. 46-22518, No. 46-22518,
Publication No. 22519, Publication No. 51-1129, Japanese Unexamined Patent Publication No. 4
7-10785, 51-88226, 51-93324, 53-87227, etc.).
これらの感光体は、実用上差支えない程度の電子写真感
度を持ってはいるが、未だ充分満足するまでには到って
いない。Although these photoreceptors have electrophotographic sensitivity to a level that is acceptable for practical use, they have not yet reached a level of sufficient electrophotographic sensitivity.
本発明の目的は極めて優れた電子写真感度を有する共晶
錯体感光層を形威した感光体を提供することにある。An object of the present invention is to provide a photoreceptor incorporating a eutectic complex photosensitive layer having extremely excellent electrophotographic sensitivity.
更に詳しくは，正′ｔｒ電時に特に優れた電子写真感度
を有する共晶錯体感光層を形或した感光体を提供するこ
とにある。More specifically, it is an object of the present invention to provide a photoreceptor having a eutectic complex photosensitive layer having particularly excellent electrophotographic sensitivity under positive t-voltage.
本発明の他の目的は、容易にＨ造できる電子写真感光体
を提供することにある。Another object of the present invention is to provide an electrophotographic photoreceptor that can be easily manufactured.
本発明者らは、ピリリウム系染料および電気絶縁性重合
体（電気絶縁性フィルム形或性重合体物質）からなる共
晶錯体に下記一般式（１）で示される化合物
（式中、Ｒ１． Ｒ３及びＲ４は水素原子、アミノ基、
アルコキシ基、チオアルコキシ基、アリールオキシ基、
メチレンジオキシ基、置換もしくは無置換のアルキル基
、ハロゲン原子又は置換もしくは無置換のアリール基を
、Ｒ２は水素原子、アルコキシ基、置換もしくは無置換
のアルキル基又はハロゲンを表わす。The present inventors have developed a compound represented by the following general formula (1) (in the formula, R1.R3 and R4 is a hydrogen atom, an amino group,
alkoxy group, thioalkoxy group, aryloxy group,
R2 represents a methylenedioxy group, a substituted or unsubstituted alkyl group, a halogen atom, or a substituted or unsubstituted aryl group, and R2 represents a hydrogen atom, an alkoxy group, a substituted or unsubstituted alkyl group, or a halogen.
但し、Ｒｉ． Ｒ２，Ｒ３およびＲ４がすべて水素原子
である場合は除く。またｋ，１２，ｍ及びｎは１，２，
３又は４の整数であり、各々が２、３又は４の整数の時
は前記Ｒ”，Ｒ”Ｒ３及びＲ４は同一でも異なっていて
もよい。）を添加することによって、極めて優れた電子
写真感度が得られることを見い出し、本発明に到った。However, Ri. Except when R2, R3 and R4 are all hydrogen atoms. Also, k, 12, m and n are 1, 2,
is an integer of 3 or 4, and when each is an integer of 2, 3 or 4, the above R'', R''R3 and R4 may be the same or different. ) was found to provide extremely excellent electrophotographic sensitivity, leading to the present invention.
従って、本発明の電子写真感光体はピリリウム系染料、
電気絶縁性重合体および前記一般式（１）で示される化
合物を主成分とする光導電層（共晶錯体感光層）が導電
性基体上に設けられていることを特徴とするものである
。Therefore, the electrophotographic photoreceptor of the present invention contains pyrylium dye,
It is characterized in that a photoconductive layer (eutectic complex photosensitive layer) containing an electrically insulating polymer and a compound represented by the general formula (1) as main components is provided on a conductive substrate.
以下，図面にそって、本発明をさらに説明する。The present invention will be further explained below with reference to the drawings.
第１図は、本発明の電子写真感光体の構或例を示す断面
図であり、導電性基体１１上に，共晶錯体感光，Ｉｉｌ
５が設けられている。FIG. 1 is a sectional view showing an example of the structure of the electrophotographic photoreceptor of the present invention, in which a eutectic complex photoreceptor, an Iil
5 is provided.
第２図は、本発明の別の構成例であり、導電性基体と共
晶錯体感光層との間に下引層ｌ４を設けたものである。FIG. 2 shows another example of the structure of the present invention, in which a subbing layer 14 is provided between the conductive substrate and the eutectic complex photosensitive layer.
また第３図ａに、本発明の電子写真用複合感光体を示す
．導電性基体上に、共晶錯体感光層を透過する光に対し
て感度を有する感光層１２（以下、第２感光層という）
を設け、さらにその上に共晶錯体感光層を設けたもので
ある。Further, FIG. 3a shows a composite photoreceptor for electrophotography according to the present invention. A photosensitive layer 12 (hereinafter referred to as a second photosensitive layer) sensitive to light transmitted through the eutectic complex photosensitive layer is formed on a conductive substrate.
is provided, and a eutectic complex photosensitive layer is further provided thereon.
第３図ｂは、電子写真用複合感光体の別の構成例を示す
ものであり、第２感光層と、共晶錯体感光層の間に中間
１′Ｉ１３を、設けてなるものである。FIG. 3b shows another structural example of a composite photoreceptor for electrophotography, in which an intermediate layer 1'I13 is provided between the second photosensitive layer and the eutectic complex photosensitive layer.
導体性基体１１としては、体積抵抗１０１ｏΩｃＩ１以
下の導電性を示すもの、例えば、アルミニウム、ニッケ
ル、クロム、ニクロム、銅、銀、金、白金などの金属、
酸化スズ，酸化インジウムなどの金ｉｉ．．ｍ化物を、
蒸着又は、スパッタリングにより、フィルム状もしくは
円筒状のプラスチック、紙に被覆したもの，あるいは、
アルミニウム、アルミニウム合金、ニッケル、ステンレ
ス等の板およびそれらをＤ．Ｉ。、Ｉ．Ｉ。、押出し、
引抜き等の工法で素管化後、切削、超仕上げ、研磨等で
表面処理した管等を使用することができる，
前述した様に、共晶錯体感光層ｌ５は、共晶錯体と、前
記一般式（１）で示される導電性物質を主或分として形
或されている，ここでの共晶錯体は、ピリリウム系染料
と、電気絶縁性重合体とからつくられるものである。As the conductive substrate 11, materials exhibiting conductivity with a volume resistance of 101 oΩcI1 or less, for example, metals such as aluminum, nickel, chromium, nichrome, copper, silver, gold, platinum, etc.
Gold such as tin oxide, indium oxide, etc. ii. ．． m-ide,
Film-like or cylindrical plastic or paper coated by vapor deposition or sputtering, or
D. plates of aluminum, aluminum alloy, nickel, stainless steel, etc. I. ,I. I. , extrusion,
It is possible to use a tube that has been made into a blank tube by a method such as drawing, and then surface-treated by cutting, superfinishing, polishing, etc. The eutectic complex mainly composed of a conductive substance represented by formula (1) is made from a pyrylium dye and an electrically insulating polymer.
ピリリウム系染料には、ピリリウム塩、チアピリリウム
塩及びセ１ノナピリリウム塩の３種があり、下記一般式
を有している。There are three types of pyrylium dyes: pyrylium salts, thiapyrylium salts, and se1nonapyrylium salts, and they have the following general formula.
ａｂｅｄ
上式において、Ｒ ，Ｒ ．Ｒ ，Ｒ 及びｅ
Ｒ は各々下記の（ａ）、（ｂ）、（ｃ）及び（ｄ）の
群から選択される基であり、
（ａ）： 水素原子、
（ｂ）； アルキル基，代表的にはメチル、エチル、プ
ロビル、イソプロビル、ブチル、ｔ−ブチル、アミル，
イソアミル、ヘキシル、オクチル、ノニル，ドデシルな
どの０１〜Ｃよ，のアルキル基、
（Ｃ）； メトキシ、エトキシ，プロポキシ、ブトキシ
、アミロキシ、ヘキソキシ、オクトキシなどのアルコキ
シ基、
（ｄ）； フェニル、４−ジフエニル、４−エチルフ
エニル、４−プロビルフェニルなどのアルキルフェニル
類；４−エトキシフェニル、４−メトキシフェニル，４
−アミ口キシフェニル、２−ヘキソキシフェニル、２−
メトキシフェニル、３，４一ジメトキシフェニルなどの
アルコキシフェニル類；２−ヒドロキシェトキシフェ二
ル、３−ヒドロキシエトキシフェニルなどのβ−ヒドロ
キシアルコキシフェニル類；４−ヒドロキシフェニル、
２，４一ジクロロフェニル、３．４−ジブロモフェニル
、４−クロロフェニル、３，４一ジクロロフェニルなど
のハロフェニル類；アジドフェニル、ニトロフェニル，
４−ジエチルアミノフェニル、４−ジメチルアミノフェ
ニルなどのアミノフェニル類；ナフチル，スチリル、メ
トキシスチリル．ジエトキシスチリル、ジメチルアミノ
スチリル，１−ブチル−４−ｐ−ジメチルアミノフェニ
ル−１，３−ブタジエニル、β一エチル−４−ジメチル
アミノスチリル等のビニル置換アリール基のような置換
アリール基を含めたアリール基、
を表わし，Ｘは硫黄、酸素又はセレン原子であり、また
Ｚ一はバークロレート，フルオロボレート、沃化物，塩
化物，臭化物、硫酸塩、過沃化物、ｐ一トルエンスルホ
ネート、ヘキサフルオロホスフェートなどの陰イオン官
能基である。abed In the above formula, R , R . R , R and e R are each a group selected from the following groups (a), (b), (c) and (d), (a): hydrogen atom, (b): alkyl group, representative Examples include methyl, ethyl, proyl, isopropyl, butyl, t-butyl, amyl,
Alkyl groups from 01 to C such as isoamyl, hexyl, octyl, nonyl, dodecyl, etc.; (C); alkoxy groups such as methoxy, ethoxy, propoxy, butoxy, amyloxy, hexoxy, octoxy; (d); phenyl, 4- Alkylphenyls such as diphenyl, 4-ethylphenyl, 4-probylphenyl; 4-ethoxyphenyl, 4-methoxyphenyl, 4
-amixoxyphenyl, 2-hexoxyphenyl, 2-
Alkoxyphenyls such as methoxyphenyl and 3,4-dimethoxyphenyl; β-hydroxyalkoxyphenyls such as 2-hydroxyethoxyphenyl and 3-hydroxyethoxyphenyl; 4-hydroxyphenyl,
Halophenyls such as 2,4-dichlorophenyl, 3,4-dibromophenyl, 4-chlorophenyl, 3,4-dichlorophenyl; azidophenyl, nitrophenyl,
Aminophenyls such as 4-diethylaminophenyl and 4-dimethylaminophenyl; naphthyl, styryl, methoxystyryl. Including substituted aryl groups such as vinyl substituted aryl groups such as diethoxystyryl, dimethylaminostyryl, 1-butyl-4-p-dimethylaminophenyl-1,3-butadienyl, β-1ethyl-4-dimethylaminostyryl, etc. represents an aryl group, X is a sulfur, oxygen or selenium atom, and Z is berchlorate, fluoroborate, iodide, chloride, bromide, sulfate, periodide, p-toluenesulfonate, hexafluorophosphate It is an anionic functional group such as.
更にＲａｌ Ｒｂ＃ Ｒ０１ Ｒｄ、及びＲ は共同し
てピリリウム核に融合したアリール環を完成するに必要
な原子であってもよい．
このようなピリリウム系染料の代表例を下記に示す。Furthermore, Ral Rb# R01 Rd and R may be atoms necessary to complete the aryl ring fused to the pyrylium nucleus. Representative examples of such pyrylium dyes are shown below.
ロレート
エート
ェニルヒリリワムバーク口レート
クレート
ト
２８
６−（３・４−ジエトキシーβ−アミルスチート
レート
一ト
チリル）−２・４−シフェニルピリリウムフルオロボレ
ート
一ト
一ト
ート
−ト
ロレート
サルフェート
一ト
ビス（４−メトキシフェニル）テアビリリウムパーク口
レート
レート
一ト
リウムパークロレート
ロポレート
ート
−ト
（ｂ）セレナピリリウムパークロレー
ト
クロレート
クロレート
８９
４−（４−ジメチルアミノフエニル）−２・６一ジフェ
ニルピリリウムへキサフル
オロフオスフェート
特に有用なピリリウム染料は下記一般式を有するもので
ある。lolate ethenyl pyrylium bark chlorate crate 28 6-(3,4-diethoxy β-amyl schitorate monototyryl)-2,4-cyphenylpyrylium fluoroborate 1to1 trolate sulfate 1tobis( 4-Methoxyphenyl) theabyrylium perchlorate chlorate monothorium perchlorate chlorate chlorate (b) selenapyrylium perchlorate chlorate chlorate 89 4-(4-dimethylaminophenyl)-2,6-diphenylpyrylium Hexafluorophosphate A particularly useful pyrylium dye is one having the general formula:
Ｒ，
式中Ｒエ及びＲ３はＣエ〜Ｃ６のアルキル基及びＣ〜Ｃ
６のアルコキシ基から選ばれた少なくとも１つの置換基
を有する置換フエニル基のようなアリール基であり、Ｒ
３はアルキル部分がＣエ〜Ｃ６のアルキルアミノ置換フ
エニル基で、ジアルキルアミノ置換及びハロアルキルア
ミノ置換フェニル基でもよい，Ｘは酸素、硫黄又はセレ
ン原子、Ｚ−は前述の通りである。R, where R and R3 are C-C6 alkyl groups and C-C
is an aryl group such as a substituted phenyl group having at least one substituent selected from the alkoxy groups of R
3 is an alkylamino-substituted phenyl group in which the alkyl moiety is C-C6, and may also be a dialkylamino-substituted or haloalkylamino-substituted phenyl group, X is oxygen, sulfur or selenium atom, and Z- is as described above.
電気絶縁性重合体としては主鎖（繰返し単位）中に下記
式で示されるアルキリデンジアリーレン部分を有するも
のが特に有用である．Ｒ，
式中Ｒ４及びＲ，は夫々、水素原子、トリフルオロメチ
ルのような置換アルキル基を含むメチル、エチル、プロ
ビル、イソプロビル、プチル、ｔ一ブチル、ベンチル，
ヘキシル、ヘプチル、オクチル、ノニル、デシルなどの
アルキル基、ハロゲン、Ｃｉ〜Ｃ，のアルキル基のよう
な置換基を有する置換アリール基を含むフェニル及びナ
フチルなどのアリール基であり、またＲ４とＲ，とは共
同してシクロヘキシルのようなシクロアルカン類及びノ
ルボルニルのようなポリシクロアルカン類を含む環式炭
化水素基を形或するに必要な炭素原子であってもよい．
Ｒ６及びＲ７は水素、０１〜Ｃ１のアルキル基又はクロ
ル、ブロム、
沃素などのハロゲンであり、
またＲ，は
ＯＳ
一ｏ−ｃ−ｏ− −ｏ−ｃ−ｏ−
０
−Ｃ−Ｏ−
０
Ｉ１
−Ｃ−０−ＣＨ，−
Ｏ
Ｏ ＣＨ３
［１１
−Ｃ−０−ＣＨ−
０
よりなる群から選択された２価の基である。As electrically insulating polymers, those having an alkylidene diarylene moiety represented by the following formula in the main chain (repeat unit) are particularly useful. R, where R4 and R each represent a hydrogen atom, methyl containing a substituted alkyl group such as trifluoromethyl, ethyl, proyl, isopropyl, butyl, t-butyl, benzyl,
aryl groups such as phenyl and naphthyl, including substituted aryl groups having substituents such as alkyl groups such as hexyl, heptyl, octyl, nonyl, decyl, halogen, alkyl groups of Ci to C, and aryl groups such as phenyl and naphthyl; may be the carbon atoms necessary to jointly form a cyclic hydrocarbon group including cycloalkanes such as cyclohexyl and polycycloalkanes such as norbornyl.
R6 and R7 are hydrogen, an alkyl group of 01 to C1, or a halogen such as chloro, bromine, or iodine, and R is OS 1o-c-o- -o-c-o- 0 -C-O- 0 It is a divalent group selected from the group consisting of I1 -C-0-CH, - O O CH3 [11 -C-0-CH- 0 ].
また下記式の繰返し単位からなる疎水性炭酸塩重合体類
（ポリカーボネー１−）も有用で好ましいものである。Hydrophobic carbonate polymers (polycarbonate 1-) comprising repeating units of the following formula are also useful and preferred.
Ｒ４０
１１
−Ｒ−Ｃ−Ｒ−０−Ｃ−０−
１
Ｒ．
式中、Ｒはハロ置換フェニレン基類及びアルキル置換フ
ェニレン基類を含むフェニレン基であり、またＲ．及び
Ｒ５は前述の通りである。これらの重合体はｔＪｓＰ３
，０２８，３６５号、同３，３１７，４６６号に開示さ
れている．好ましくは、ビスフェノールＡから製造され
るような、繰返し単位に７ルキリデンジアリーレン部分
を含有しジフェニルカーボネートと２，２−ビス（４−
ヒドロキシフェニル）プロパンとの間のエステル交換に
よって生成した重合体を含むポリカーボネート類が有用
である．このような重合体はＵＳＰ２，９９９，７５０
号、同３，０３８，８７４号、同３，０３８，８８０号
、同３，１０６，５４４号、同３，１０６，５４５号、
同３，１０６，５４６号等に開示されている。いずれに
してもフィルム形或性ボリカーボネート樹脂類は広範囲
に使用できる。特に約０．５〜１．８の固有粘度を有す
るものを使用すると、満足し得る結果が得られる．電気
絶縁性重合体の具体例は下記の通りである。R40 11 -R-C-R-0-C-0- 1 R. In the formula, R is a phenylene group including halo-substituted phenylene groups and alkyl-substituted phenylene groups, and R. and R5 are as described above. These polymers are tJsP3
, No. 028,365 and No. 3,317,466. Preferably, it contains a 7-alkylidene diarylene moiety in the repeating unit, such as made from bisphenol A, diphenyl carbonate and 2,2-bis(4-
Polycarbonates containing polymers formed by transesterification with (hydroxyphenyl)propane are useful. Such polymers are USP 2,999,750
No. 3,038,874, No. 3,038,880, No. 3,106,544, No. 3,106,545,
It is disclosed in No. 3,106,546, etc. In any case, polycarbonate resins in film form can be used in a wide variety of ways. Particularly satisfactory results are obtained when using those having an intrinsic viscosity of about 0.5 to 1.8. Specific examples of the electrically insulating polymer are as follows.
３
ポリ（４，４’−イソプロピリデンジフェニレンカーボ
ネートーｃｏ−テレフタ１ノート）ｌ５
ポリ（４．４’−イソプロビリデンジフェニレェニレン
力ボネート』
（以下余白）
また一般式（Ｉ）
で示される化合物の代表例
を下記に示す。3 Poly(4,4'-isopropylidene diphenylene carbonate co-terephthalate)l5 Poly(4,4'-isopropylidene diphenylene carbonate co-terephthalate carbonate) (hereinafter referred to as the margin) Also represented by general formula (I) Representative examples of the compounds are shown below.
本発明の共晶錯体感光ＮＩ１５をつくるには、上記のピ
リリウム系染料、電気絶縁性重合体、および一般式（１
）で示される化合物を適当な溶媒例えば、テトラヒドロ
フラン、トルエン、１，２−ジクロルエタン、塩化メチ
レン、クロロホルム、モノクロルベンゼン、ジクロルベ
ンゼン、ベンゼンなどに溶解し、これを導電性基体１１
上に塗布し、５０〜１３０℃で乾燥して、膜厚５〜５０
μｍの光導電層（共晶錯体感光層）１５を形或すればよ
い．
塗布は浸漬塗工法、ビードコート法、スプレーコート法
や、ワイヤーブレード、ドクターブレード、エアーナイ
フなどを用いて行なえる．この塗布乾燥がなされる間に
、ピリリウム系染料と電気絶縁性重合体とで共晶錯体を
形成する。To make the eutectic complex photosensitive NI15 of the present invention, the above pyrylium dye, electrically insulating polymer, and general formula (1
) is dissolved in a suitable solvent such as tetrahydrofuran, toluene, 1,2-dichloroethane, methylene chloride, chloroform, monochlorobenzene, dichlorobenzene, benzene, etc., and this is added to the conductive substrate 11.
Coat on top and dry at 50-130℃ to obtain a film thickness of 5-50℃.
It is sufficient to form a photoconductive layer (eutectic complex photosensitive layer) 15 with a thickness of μm. Application can be done using dip coating, bead coating, spray coating, wire blade, doctor blade, air knife, etc. During this coating and drying process, a eutectic complex is formed between the pyrylium dye and the electrically insulating polymer.
共晶錯体感光層１５における各或分の割合は、ピリリウ
ム系染料１重量部に対して、電気絶縁性重合体５〜８０
重量部，好ましくは７〜４０重量部、前記一般式（１）
で示される化合物１〜５０重量部、好ましくは３〜３０
重量部が適当である。The proportion of each part in the eutectic complex photosensitive layer 15 is 5 to 80 parts by weight of the electrically insulating polymer per 1 part by weight of the pyrylium dye.
Parts by weight, preferably 7 to 40 parts by weight, the general formula (1)
1 to 50 parts by weight, preferably 3 to 30 parts by weight of a compound represented by
Parts by weight are appropriate.
また、この１１５を形或する際に、シリコーンオイルな
どのレベリング剤を、塗工液に添加してもよい。その使
用量は、電気絶縁性重合体に対してＯ〜１重量％程度が
適当である。Further, when forming this 115, a leveling agent such as silicone oil may be added to the coating liquid. The appropriate amount to be used is about 0 to 1% by weight based on the electrically insulating polymer.
さらに、層ｌ５を設けるに際して，結着剤が必要により
使用されてもよい。Furthermore, when providing the layer 15, a binder may be used if necessary.
ここでの結着剤材料としてはポリエチレン、ポリスチレ
ン，ポリブタジェン、スチレンーブタジエン共重合体、
アクリル酸エステル又はメタクリル酸エステルの重合体
及び共重合体、ポリエステル，ポリアミド、エポキシ樹
脂，ウレタン樹脂，シリコン樹脂、アルキッド樹脂、セ
ルロース系樹脂やポリーＮ−ビニル力ルバゾール及びそ
の誘導体（例えばカルバゾール骨格に塩素、臭素などの
ハロゲン、メチル基、アミノ基などの置換基を有するも
の），ポリビニルビレン、ポリビニルアントラセン、ビ
レンーホルムアルテヒド縮重合体及びその誘導体（例え
ばピレン骨格に臭素などのハロゲン、ニトロ基などの置
換基を有するもの），ポリーγ一カルバゾリルエチルー
Ｌ−ダルタメート、スチロール樹脂、塩素化ポリエチレ
ン、アセタール樹脂、メラミン樹脂などがあげられる。The binder materials used here include polyethylene, polystyrene, polybutadiene, styrene-butadiene copolymer,
Polymers and copolymers of acrylic esters or methacrylic esters, polyesters, polyamides, epoxy resins, urethane resins, silicone resins, alkyd resins, cellulose resins, poly-N-vinyl rubbersole and its derivatives (for example, chlorine in the carbazole skeleton). , halogens such as bromine, methyl groups, substituents such as amino groups), polyvinylpyrene, polyvinylanthracene, birene-formaltehyde condensation polymers and their derivatives (for example, pyrene skeletons with halogens such as bromine, nitro groups, etc.) ), poly γ-carbazolylethyl-L-daltamate, styrene resin, chlorinated polyethylene, acetal resin, melamine resin, etc.
この結着剤には，可塑剤を併用することができる。可塑
剤としてはジブチルフタレート、ジオクチルフタレート
など一般に樹脂の可塑剤として使用されているものが、
そのまま使用できる。A plasticizer can be used in combination with this binder. Plasticizers that are commonly used as plasticizers for resins include dibutyl phthalate and dioctyl phthalate.
It can be used as is.
その使用量は，樹脂結着剤に対してＯ〜３０重量％程度
が適当である。The amount used is approximately 0 to 30% by weight based on the resin binder.
なお、本発明の共晶錯体感光層ｌ５を形或するに際して
は、塗工液を重ね塗り方法（特開昭５６−４０８３７号
公報）や、既に設けた電気絶縁性重合体層をピリリウム
系染料に浸漬後、乾燥する方法（特開昭５６−８００５
２号公報）を用いてもよく、また、層１５中のピリリウ
ム系染料の濃度を導電性基体側と、表面付近で異にする
ように形成（特開昭５６−１２１０４２号公報）しても
よい。Note that when forming the eutectic complex photosensitive layer 15 of the present invention, the method of overcoating the coating liquid (Japanese Unexamined Patent Publication No. 56-40837) or the coating of the already formed electrically insulating polymer layer with pyrylium dye Method of drying after soaking in
(Japanese Unexamined Patent Publication No. 121042/1982) may be used, or the layer 15 may be formed so that the concentration of the pyrylium dye is different on the conductive substrate side and near the surface. good.
本・発明において第２図トこ示されるように導電性基体
と、共晶錯体感光層の間に下引層ｌ４を設けることによ
り、帯電性、接着性を改良することができる。In the present invention, as shown in FIG. 2, by providing a subbing layer 14 between the conductive substrate and the eutectic complex photosensitive layer, charging properties and adhesion properties can be improved.
下引層１４には、Ｓｉｎ，Ａｎ８０，等の無機材料を蒸
着、スパッタリング、陽極酸化などの方法で設けたもの
や、ポリアミド樹脂、アルコール可溶性ナイロン樹脂，
水溶性ポリビニルブチラール樹脂、ポリビニルブチラー
ル樹脂などの樹脂層を用いることもできる。The undercoat layer 14 may be made of an inorganic material such as Sin, An80, etc., provided by vapor deposition, sputtering, or anodization, or may be made of polyamide resin, alcohol-soluble nylon resin,
A resin layer made of water-soluble polyvinyl butyral resin, polyvinyl butyral resin, etc. can also be used.
また、上記樹脂下引層にＺｎＯ＋ ＴｉＯ．ＺｎＳ等の
顔料粒子を分散したものも、下引層として用いることが
できる。Further, ZnO+TiO. A dispersion of pigment particles such as ZnS can also be used as the undercoat layer.
更に、本発明の下引，１１！Ｆ１４として、シランカッ
プリング剤、チタンカップリング剤、クロムカップリン
グ剤等を使用することもできる。Furthermore, subtraction of the present invention, 11! As F14, a silane coupling agent, a titanium coupling agent, a chromium coupling agent, etc. can also be used.
下引層１４の膜厚はＯ〜５μｍが適当である。The thickness of the undercoat layer 14 is suitably 0 to 5 μm.
また、本発明において、共晶錯体感光層１５上に保護層
や絶縁層を設けることも可能である。Further, in the present invention, it is also possible to provide a protective layer or an insulating layer on the eutectic complex photosensitive layer 15.
保護層は感光体の表面保護の目的で設けられ、これに使
用される材料としてはＡＢＳ樹脂、ＡＣＳｍ脂、オレフ
ィン〜ビニルモノマー共重合体、塩素化ポリエーテル、
アリル樹脂、フェノール樹脂、ポリアセタール、ボリア
ミド、ポリアミドイミド、ポリアクリレート、ポリアリ
ルスルホン、ポリブチレン、ポリブチレンテレフタ１ノ
ート，ポリカーボネート，ポリエーテルスルホン、ポリ
エチレン、ポリエチレンテレフタレート、ポリイミド，
アクリル樹脂、ポリメチルベンテン，ボリプロビレン，
ポリフェニレンオキシド、ボリスルホン、ポリスチレン
、ＡＳ樹脂、ブタジエンースチレン共重合体、ポリウレ
タン，ポリ塩化ビニル，ポリ塩化ビニリデン、エポキシ
樹脂等の樹脂が挙げられる．保護層にはその他、耐摩耗
性を向上する目的でポリテトラフルオ口エチレンのよう
なフッ素樹脂，シリコーン樹脂及びこれら樹脂に酸化チ
タン、酸化錫、チタン酸カリウム等の無機材料を分散し
たもの等を添加することができる。保護層の形成法とし
ては通常の塗布法が採用される。なお保護層の厚さは０
．５〜１０μｍ程度が適当である．絶縁層には、先に挙
げた共晶錯体感光層に使用してもよい結着剤材料がその
まま使用でき、結着剤材料を含んだ溶液を塗布し，もう
けることができる。この他、ポリ塩化ビニル、ポリプロ
ピレン、ポリエステル、ポリスチレン、ポリ塩化ビニリ
デン、ポリエチレン、塩化ゴム、テフロンなどの熱収縮
フィルムもしくはチューブを用いることもできる。The protective layer is provided for the purpose of protecting the surface of the photoreceptor, and materials used for this include ABS resin, ACSm resin, olefin-vinyl monomer copolymer, chlorinated polyether,
Allyl resin, phenolic resin, polyacetal, polyamide, polyamideimide, polyacrylate, polyallyl sulfone, polybutylene, polybutylene terephthalate, polycarbonate, polyether sulfone, polyethylene, polyethylene terephthalate, polyimide,
Acrylic resin, polymethylbentene, polypropylene,
Examples include resins such as polyphenylene oxide, borisulfone, polystyrene, AS resin, butadiene-styrene copolymer, polyurethane, polyvinyl chloride, polyvinylidene chloride, and epoxy resin. In addition, the protective layer may also contain fluororesins such as polytetrafluoroethylene, silicone resins, and inorganic materials such as titanium oxide, tin oxide, potassium titanate, etc. dispersed in these resins for the purpose of improving wear resistance. Can be added. A normal coating method is adopted as a method for forming the protective layer. The thickness of the protective layer is 0.
．． Approximately 5 to 10 μm is appropriate. For the insulating layer, the binder material that may be used in the eutectic complex photosensitive layer mentioned above can be used as is, or a solution containing the binder material can be applied. In addition, heat-shrinkable films or tubes made of polyvinyl chloride, polypropylene, polyester, polystyrene, polyvinylidene chloride, polyethylene, chlorinated rubber, Teflon, etc. can also be used.
本発明の例として、第３図ａ、第３図ｂに示す様な電子
写真用複合感光体が挙げられる。An example of the present invention is a composite photoreceptor for electrophotography as shown in FIGS. 3a and 3b.
第２感光層１２および中間層１３には、公知の材料（例
えば、特開昭５６−１２１０４４号公報）を用いること
ができ、第１感光層には、前述した共晶錯体感光層１５
を用いることができる。For the second photosensitive layer 12 and the intermediate layer 13, known materials (for example, JP-A-56-121044) can be used, and for the first photosensitive layer, the above-mentioned eutectic complex photosensitive layer 15 can be used.
can be used.
この様にしてなる電子写真用複合感光体には、公知のプ
ロセス（例えば特開昭５６−１２１０４４号）を適用し
て画像形或することができる。An image can be formed on the composite photoreceptor for electrophotography formed in this manner by applying a known process (for example, Japanese Patent Application Laid-open No. 121044/1983).
塩化メチレン
６５０重量部
の組或よりなる塗工液を、ＡＩ２を蒸着したポリエチレ
ンテレフタレート・フィルム上に塗布・乾燥し、乾燥膜
厚１６μｍの共晶錯体感光層を形威した。A coating solution consisting of 650 parts by weight of methylene chloride was applied onto a polyethylene terephthalate film on which AI2 had been deposited and dried to form a eutectic complex photosensitive layer with a dry film thickness of 16 μm.
止ＪＪＬ二Ｌ
実施例−１における（１）式の化合物の代りに，下記構
造式（ｎ）のトリフェニルメタン化合物を使用した他は
、すべて実施例−１と同様にして、感光層を形威した。A photosensitive layer was formed in the same manner as in Example-1 except that a triphenylmethane compound of the following structural formula (n) was used instead of the compound of formula (1) in Example-1. Intimidated.
以上の様にして得られた感光体を、エレクトロスタティ
ック・ペーパーアナライザ（ＳＰ−４２８（株）川口電
機製作所製〕に取りつけ，コロナ放電々圧−５ ． ５
ｋｖまたは、＋６．Ｏｋｖで帯電１０秒後の電位Ｖａ（
Ｖ）、暗減衰１０秒後の電位Ｖｏ（Ｖ）、強度１０１２
ｕｘでの露光１５秒後の残留電気ｖｍ（ｖ）、さらに電
位Ｖｏを１７５に減衰させるのに必要な露光量Ｅ １／
５（息ｕｘ−ｓａｃ）を測定した．電位保持率を次の様
に定義する。The photoreceptor obtained as described above was attached to an electrostatic paper analyzer (SP-428 manufactured by Kawaguchi Electric Seisakusho Co., Ltd.), and the corona discharge pressure was -5.5.
kv or +6. Potential Va(
V), potential Vo (V) after 10 seconds of dark decay, intensity 1012
The residual electricity vm (v) after 15 seconds of exposure at ux, and the exposure amount E required to further attenuate the potential Vo to 175 1/
5 (breath ux-sac) was measured. The potential holding rate is defined as follows.
Ｖｍ
また上記条件のＩＦｍ！と露光を同時に連続１時間行な
って，感光体を疲労させた後、さらに上記と同様にして
感光体特性を測定した。Vm Also, IFm under the above conditions! After exposing the photoreceptor to light for one hour at the same time to fatigue the photoreceptor, the characteristics of the photoreceptor were further measured in the same manner as above.
結果を表−１に示す。The results are shown in Table-1.
（以下余白）
表−１
実施例−１における一般式（１）の化合物の代りに表−
２に示す化合物を用いた他はすべて実施例−１と同様に
して、感光層を形成した。(Left space below) Table-1 Table-1 instead of the compound of general formula (1) in Example-1
A photosensitive layer was formed in the same manner as in Example 1 except that the compound shown in Example 2 was used.
感光体特性の測定結果を表−２に示す。Table 2 shows the measurement results of photoreceptor characteristics.
（以下余白）
表−２
叉遣１二Ｕ
厚さ０ ． ２ｍｏ＋のＡＩ２板上に、以下の組成の下
引層塗工液および共晶錯体感光層塗工液を塗布、乾燥し
，下引Ｍ（膜厚０．３μｍ）および共晶錯体感光層（膜
厚ｌ５μｍ）を形成して，第２図に示される電子写真感
光体を作成した。(Margins below) Table 2: Fork 12U Thickness: 0. A subbing layer coating liquid and a eutectic complex photosensitive layer coating liquid having the following compositions were applied onto a 2mo+ AI2 board, dried, and the subbing layer M (thickness: 0.3 μm) and eutectic complex photosensitive layer (film thickness) were coated and dried. The electrophotographic photoreceptor shown in FIG. 2 was prepared by forming a film having a thickness of 15 μm.
（１）下引層塗工液
エタノール ３００重量部（２）共
晶錯体感光層塗工液
表−３に示す一般式（１）の化合物 ２５重量部塩化メ
チレン ＳＯＯ重量部クロロホルム
１５０ｉｉ量部裏艶量二主
実施例８〜ｌ４における一般式（１）の化合物の代りに
比較例−１で用いた構造式（ｎ）のトリフェニルメタン
化合物を使用した他は、すべて、実施例＆〜１４と、同
様にして感光体を作成した。(1) Undercoat layer coating liquid Ethanol 300 parts by weight (2) Eutectic complex photosensitive layer coating liquid Compound of general formula (1) shown in Table 3 25 parts by weight Methylene chloride SOO parts by weight Chloroform
150ii parts, parts, back gloss, 2, main examples 8 to 14, except that the triphenylmethane compound of structural formula (n) used in comparative example-1 was used instead of the compound of general formula (1). A photoreceptor was prepared in the same manner as in Example &~14.
感光体特性の測定結果を表−３に示す。Table 3 shows the measurement results of photoreceptor characteristics.
（以下余白）
１３６９
表−３
〔効 果〕
本発明により、優れた電子写真感度（正Ｓ電時において
特に優れた電子写真感度）を有する共晶錯体感光層から
成る電子写真感光体及び２色プロセス用の電子写真用複
合感光体を提供することができる．(The following is a blank space) 1369 Table 3 [Effects] According to the present invention, an electrophotographic photoreceptor comprising a eutectic complex photosensitive layer having excellent electrophotographic sensitivity (particularly excellent electrophotographic sensitivity at positive S voltage) and a two-color It is possible to provide a composite photoreceptor for electrophotography for process use.
第１図は、本発明の電子写真感光体の断面図、第２図は
、本発明の他の電子写真感光体の断面図、第３図ａは、
本発明の電子写真複合感光体の断面図、第３図ｂは，本
発明の他の電子写真用複合感光体の断面図である。
１ｌ・・・導電性基体 １２・・・感光Ｎ（第２感光
層）Ｌ３・・・中間層 １４・・・下引層１５・
・・感光層（共晶錯体）FIG. 1 is a sectional view of an electrophotographic photoreceptor of the present invention, FIG. 2 is a sectional view of another electrophotographic photoreceptor of the invention, and FIG.
FIG. 3b is a sectional view of another electrophotographic composite photoreceptor of the present invention. 1l... Conductive substrate 12... Photosensitive N (second photosensitive layer) L3... Intermediate layer 14... Undercoat layer 15.
・Photosensitive layer (eutectic complex)
Claims (1)
体および下記一般式（ I ）で示される化合物を主成分
とする光導電層が設けられていることを特徴とする電子
写真感光体。 ▲数式、化学式、表等があります▼（ I ） （式中、Ｒ＾１、Ｒ＾３及びＲ＾４は水素原子、アミノ
基、アルコキシ基、チオアルコキシ基、 アリールオキシ基、メチレンジオキシ基、置換もしくは
無置換のアルキル基、ハロゲン原子又は置換もしくは無
置換のアリール基を、Ｒ＾２は水素原子、アルコキシ基
、置換もしくは無置換のアルキル基又はハロゲンを表わ
す。但し、Ｒ＾１、Ｒ＾２、Ｒ＾３およびＲ＾４がすべ
て水素原子である場合は除く。 またｋ、ｌ、ｍ及びｎは１、２、３又は４の整数であり
、各々が２、３又は４の整数の時は前記Ｒ＾１、Ｒ＾２
、Ｒ＾３及びＲ＾４は同一でも異なっていてもよい。）[Claims] 1. A photoconductive layer comprising a pyrylium dye, an electrically insulating polymer, and a compound represented by the following general formula (I) as main components is provided on a conductive substrate. Electrophotographic photoreceptor. ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (I) (In the formula, R^1, R^3 and R^4 are hydrogen atoms, amino groups, alkoxy groups, thioalkoxy groups, aryloxy groups, methylenedioxy groups , a substituted or unsubstituted alkyl group, a halogen atom, or a substituted or unsubstituted aryl group, and R^2 represents a hydrogen atom, an alkoxy group, a substituted or unsubstituted alkyl group, or a halogen.However, R^1, R Except when ^2, R^3, and R^4 are all hydrogen atoms. Also, k, l, m, and n are integers of 1, 2, 3, or 4, and each is an integer of 2, 3, or 4. When , the above R^1, R^2
, R^3 and R^4 may be the same or different. )
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19456389A JP2822345B2 (en) | 1989-07-27 | 1989-07-27 | Electrophotographic photoreceptor |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19456389A JP2822345B2 (en) | 1989-07-27 | 1989-07-27 | Electrophotographic photoreceptor |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0358054A true JPH0358054A (en) | 1991-03-13 |
| JP2822345B2 JP2822345B2 (en) | 1998-11-11 |
Family
ID=16326613
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP19456389A Expired - Fee Related JP2822345B2 (en) | 1989-07-27 | 1989-07-27 | Electrophotographic photoreceptor |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2822345B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5456989A (en) * | 1993-11-24 | 1995-10-10 | Fuji Electric Co., Ltd. | Photosensitive body for electrophotography |
| US5495049A (en) * | 1993-03-22 | 1996-02-27 | Fuji Xerox Co., Ltd. | Triarylamine compounds useful in electrophotographic photoreceptors |
-
1989
- 1989-07-27 JP JP19456389A patent/JP2822345B2/en not_active Expired - Fee Related
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5495049A (en) * | 1993-03-22 | 1996-02-27 | Fuji Xerox Co., Ltd. | Triarylamine compounds useful in electrophotographic photoreceptors |
| US5587263A (en) * | 1993-03-22 | 1996-12-24 | Fuji Xerox Co., Ltd. | Electrophotographic photoreceptor using triarylamine compounds |
| US5456989A (en) * | 1993-11-24 | 1995-10-10 | Fuji Electric Co., Ltd. | Photosensitive body for electrophotography |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2822345B2 (en) | 1998-11-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |