JPS63159860A - Electrophotographic sensitive body - Google Patents
Electrophotographic sensitive bodyInfo
- Publication number
- JPS63159860A JPS63159860A JP31384586A JP31384586A JPS63159860A JP S63159860 A JPS63159860 A JP S63159860A JP 31384586 A JP31384586 A JP 31384586A JP 31384586 A JP31384586 A JP 31384586A JP S63159860 A JPS63159860 A JP S63159860A
- Authority
- JP
- Japan
- Prior art keywords
- layer
- photoreceptor
- ctm
- cgm
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 6
- 125000001841 imino group Chemical group [H]N=* 0.000 claims abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 3
- 108091008695 photoreceptors Proteins 0.000 claims description 98
- 150000001875 compounds Chemical class 0.000 claims description 58
- 239000000126 substance Substances 0.000 claims description 26
- -1 amino, substituted amino Chemical group 0.000 claims description 14
- 239000010410 layer Substances 0.000 abstract description 86
- 230000035945 sensitivity Effects 0.000 abstract description 19
- 239000000463 material Substances 0.000 abstract description 14
- 239000011241 protective layer Substances 0.000 abstract description 7
- 239000002356 single layer Substances 0.000 abstract description 7
- 230000006750 UV protection Effects 0.000 abstract description 5
- 230000007613 environmental effect Effects 0.000 abstract description 4
- 230000003647 oxidation Effects 0.000 abstract description 4
- 238000007254 oxidation reaction Methods 0.000 abstract description 4
- 239000002131 composite material Substances 0.000 abstract description 3
- 238000002156 mixing Methods 0.000 abstract description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- 229920005989 resin Polymers 0.000 description 34
- 239000011347 resin Substances 0.000 description 34
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- 239000004419 Panlite Substances 0.000 description 6
- 206010034972 Photosensitivity reaction Diseases 0.000 description 6
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- 238000000576 coating method Methods 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- 230000036211 photosensitivity Effects 0.000 description 6
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 5
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- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
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- 239000011669 selenium Substances 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical class S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 4
- UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 3
- 229920000178 Acrylic resin Polymers 0.000 description 3
- 239000004925 Acrylic resin Substances 0.000 description 3
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 3
- 150000004056 anthraquinones Chemical class 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000003822 epoxy resin Substances 0.000 description 3
- 239000012860 organic pigment Substances 0.000 description 3
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- 229920000647 polyepoxide Polymers 0.000 description 3
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- 229920001187 thermosetting polymer Polymers 0.000 description 3
- FKNIDKXOANSRCS-UHFFFAOYSA-N 2,3,4-trinitrofluoren-1-one Chemical compound C1=CC=C2C3=C([N+](=O)[O-])C([N+]([O-])=O)=C([N+]([O-])=O)C(=O)C3=CC2=C1 FKNIDKXOANSRCS-UHFFFAOYSA-N 0.000 description 2
- WUPHOULIZUERAE-UHFFFAOYSA-N 3-(oxolan-2-yl)propanoic acid Chemical compound OC(=O)CCC1CCCO1 WUPHOULIZUERAE-UHFFFAOYSA-N 0.000 description 2
- YUXAUJNEGNCZQL-UHFFFAOYSA-N 4,10-dibromo-10h-anthracen-9-one Chemical compound C1=CC(Br)=C2C(Br)C3=CC=CC=C3C(=O)C2=C1 YUXAUJNEGNCZQL-UHFFFAOYSA-N 0.000 description 2
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical compound O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 description 2
- 102100039497 Choline transporter-like protein 3 Human genes 0.000 description 2
- 101000889279 Homo sapiens Choline transporter-like protein 3 Proteins 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- MJVAVZPDRWSRRC-UHFFFAOYSA-N Menadione Chemical compound C1=CC=C2C(=O)C(C)=CC(=O)C2=C1 MJVAVZPDRWSRRC-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- 229920002433 Vinyl chloride-vinyl acetate copolymer Polymers 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000006096 absorbing agent Substances 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 229920000180 alkyd Polymers 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 229910052980 cadmium sulfide Inorganic materials 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- 239000001023 inorganic pigment Substances 0.000 description 2
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 2
- BSIHWSXXPBAGTC-UHFFFAOYSA-N isoviolanthrone Chemical class C12=CC=CC=C2C(=O)C2=CC=C3C(C4=C56)=CC=C5C5=CC=CC=C5C(=O)C6=CC=C4C4=C3C2=C1C=C4 BSIHWSXXPBAGTC-UHFFFAOYSA-N 0.000 description 2
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- 239000000113 methacrylic resin Substances 0.000 description 2
- 239000005011 phenolic resin Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 2
- 229920001225 polyester resin Polymers 0.000 description 2
- 239000004645 polyester resin Substances 0.000 description 2
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- 239000004065 semiconductor Substances 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 2
- 229920002554 vinyl polymer Polymers 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
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- NMNSBFYYVHREEE-UHFFFAOYSA-N 1,2-dinitroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C([N+]([O-])=O)C([N+](=O)[O-])=CC=C3C(=O)C2=C1 NMNSBFYYVHREEE-UHFFFAOYSA-N 0.000 description 1
- IZUKQUVSCNEFMJ-UHFFFAOYSA-N 1,2-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1[N+]([O-])=O IZUKQUVSCNEFMJ-UHFFFAOYSA-N 0.000 description 1
- WDCYWAQPCXBPJA-UHFFFAOYSA-N 1,3-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC([N+]([O-])=O)=C1 WDCYWAQPCXBPJA-UHFFFAOYSA-N 0.000 description 1
- HJRJRUMKQCMYDL-UHFFFAOYSA-N 1-chloro-2,4,6-trinitrobenzene Chemical compound [O-][N+](=O)C1=CC([N+]([O-])=O)=C(Cl)C([N+]([O-])=O)=C1 HJRJRUMKQCMYDL-UHFFFAOYSA-N 0.000 description 1
- WPMHMYHJGDAHKX-UHFFFAOYSA-N 1-ethenylpyrene Chemical compound C1=C2C(C=C)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 WPMHMYHJGDAHKX-UHFFFAOYSA-N 0.000 description 1
- BIEFDNUEROKZRA-UHFFFAOYSA-N 2-(2-phenylethenyl)aniline Chemical class NC1=CC=CC=C1C=CC1=CC=CC=C1 BIEFDNUEROKZRA-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
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- 229940097275 indigo Drugs 0.000 description 1
- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 description 1
- 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
- 230000001678 irradiating effect Effects 0.000 description 1
- 229910000464 lead oxide Inorganic materials 0.000 description 1
- 229910052981 lead sulfide Inorganic materials 0.000 description 1
- 229940056932 lead sulfide Drugs 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- NNYHMCFMPHPHOQ-UHFFFAOYSA-N mellitic anhydride Chemical compound O=C1OC(=O)C2=C1C(C(OC1=O)=O)=C1C1=C2C(=O)OC1=O NNYHMCFMPHPHOQ-UHFFFAOYSA-N 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 description 1
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 150000007978 oxazole derivatives Chemical class 0.000 description 1
- YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical compound C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 125000001791 phenazinyl group Chemical class C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- INAAIJLSXJJHOZ-UHFFFAOYSA-N pibenzimol Chemical class C1CN(C)CCN1C1=CC=C(N=C(N2)C=3C=C4NC(=NC4=CC=3)C=3C=CC(O)=CC=3)C2=C1 INAAIJLSXJJHOZ-UHFFFAOYSA-N 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 229910052573 porcelain Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 150000004060 quinone imines Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- QXKXDIKCIPXUPL-UHFFFAOYSA-N sulfanylidenemercury Chemical compound [Hg]=S QXKXDIKCIPXUPL-UHFFFAOYSA-N 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- AUHHYELHRWCWEZ-UHFFFAOYSA-N tetrachlorophthalic anhydride Chemical compound ClC1=C(Cl)C(Cl)=C2C(=O)OC(=O)C2=C1Cl AUHHYELHRWCWEZ-UHFFFAOYSA-N 0.000 description 1
- PCCVSPMFGIFTHU-UHFFFAOYSA-N tetracyanoquinodimethane Chemical compound N#CC(C#N)=C1C=CC(=C(C#N)C#N)C=C1 PCCVSPMFGIFTHU-UHFFFAOYSA-N 0.000 description 1
- 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
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 150000007979 thiazole derivatives Chemical class 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000011282 treatment Methods 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
- 238000002604 ultrasonography Methods 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- YKSGNOMLAIJTLT-UHFFFAOYSA-N violanthrone Chemical class C12=C3C4=CC=C2C2=CC=CC=C2C(=O)C1=CC=C3C1=CC=C2C(=O)C3=CC=CC=C3C3=CC=C4C1=C32 YKSGNOMLAIJTLT-UHFFFAOYSA-N 0.000 description 1
- 229940075420 xanthine Drugs 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/05—Organic bonding materials; Methods for coating a substrate with a photoconductive layer; Inert supplements for use in photoconductive layers
- G03G5/0503—Inert supplements
- G03G5/051—Organic non-macromolecular compounds
- G03G5/0521—Organic non-macromolecular compounds comprising one or more heterocyclic groups
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
- G03G5/0622—Heterocyclic compounds
- G03G5/0624—Heterocyclic compounds containing one hetero ring
- G03G5/0635—Heterocyclic compounds containing one hetero ring being six-membered
- G03G5/0637—Heterocyclic compounds containing one hetero ring being six-membered containing one hetero atom
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は電子写真感光体に関し、特に有機光導電性電子
写真感光体の改良に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to electrophotographic photoreceptors, and more particularly to improvements in organic photoconductive electrophotographic photoreceptors.
カールソン方法の電子写真複写機においては、感光体表
面に帯電させた後、露光によって静電潜像を形成し、そ
の静電潜像をトナーによって現像し、次いでその可視像
を紙等に転写、定着させる。In an electrophotographic copying machine using the Carlson method, the surface of a photoreceptor is charged, an electrostatic latent image is formed by exposure, the electrostatic latent image is developed with toner, and the visible image is then transferred to paper, etc. , make it established.
一方、感光体には付着トナーの除去や除電、表面の清浄
化が施され、長期に亘って反復使用される。On the other hand, the photoreceptor is subjected to removal of adhered toner, neutralization of static electricity, and surface cleaning, and is used repeatedly over a long period of time.
従って、電子写真感光体としては、帯電特性および感度
が良好で更に暗減衰が小さい等の電子写真特性は勿論、
加えて繰返し使用での耐剛性、耐摩耗性、耐湿性等の物
理的性質や、コロナ放電時に発生するオゾン、露光時の
紫外線等への耐性（耐環境性）においても良好であるこ
とが要求される。Therefore, as an electrophotographic photoreceptor, it not only has good charging characteristics and sensitivity, but also has electrophotographic characteristics such as low dark decay.
In addition, it is required to have good physical properties such as rigidity resistance, abrasion resistance, and moisture resistance during repeated use, as well as resistance to ozone generated during corona discharge, ultraviolet rays during exposure, etc. (environmental resistance). be done.
従来、電子写真感光体としては、セレン、酸化亜鉛、硫
化カドミウム等の無機光導電性物質を主成分とする感光
体層を有する無機感光体が広く用いられている。Conventionally, inorganic photoreceptors having a photoreceptor layer containing an inorganic photoconductive substance such as selenium, zinc oxide, or cadmium sulfide as a main component have been widely used as electrophotographic photoreceptors.
一方、種々の有機光導電性物質を電子写真感光体の感光
体層の材料として利用することが近年活発に研究、開発
されている。On the other hand, the use of various organic photoconductive substances as materials for photoreceptor layers of electrophotographic photoreceptors has been actively researched and developed in recent years.
例えば特公昭５Ｑ−１０４９６号には、ポリ−Ｎ−ビニ
ルカルバゾールと２．４．７−ドリニトロー９−フルオ
レノンを含有した感光体層を有する有機感光体について
記載されている。しかしこの感光体は、感度及び耐久性
において必ずしも満足できるものではない。このような
欠点を改善するために、感光体層において、電荷り生機
能と電荷輸送機能とを異なる物質に個別に分担させるこ
とにより、感度が高くて耐久性の大きい有機感光体を開
発する試みがなされている。このようないわば機能分離
型の電子写真感光体においては、各機能を発揮する物質
を広い範囲のものから選択することができるので、任意
の特性を有する電子写真感光体を比較的容易に作製する
ことが可能である。For example, Japanese Patent Publication No. 5Q-10496 describes an organic photoreceptor having a photoreceptor layer containing poly-N-vinylcarbazole and 2,4,7-dolinitro-9-fluorenone. However, this photoreceptor is not necessarily satisfactory in sensitivity and durability. In order to improve these shortcomings, an attempt was made to develop an organic photoreceptor with high sensitivity and durability by assigning the charge generation function and charge transport function to different substances in the photoreceptor layer. is being done. In such so-called function-separated type electrophotographic photoreceptors, substances that exhibit each function can be selected from a wide range of materials, so it is relatively easy to produce electrophotographic photoreceptors with arbitrary characteristics. Is possible.
こうした機能分離型の電子写真感光体に有効な電荷発生
物質として、従来数多くの物質が提案されている。無機
物質を用いる例としては、例えば特公昭４３−１８１９
８号に記載されているように、無定形セレンがある。こ
れは有機電荷輸送物質と組合される。Many substances have been proposed as charge-generating substances that are effective for such functionally separated electrophotographic photoreceptors. Examples of using inorganic substances include, for example, Japanese Patent Publication No. 43-1819
As described in No. 8, there is amorphous selenium. This is combined with an organic charge transport material.
また、有機染料や有機顔料を電荷発生物質として用いた
電子写真感光体も多数提案されており、例えば、ビスア
ゾ化合物を含有する感光体層を有するものは、特開昭４
７−３７５４３号、同５５−２２８３４号、同５４−７
９６３２号、同５６−１１６０４０号等により既に知ら
れている。In addition, many electrophotographic photoreceptors using organic dyes or organic pigments as charge-generating substances have been proposed. For example, one having a photoreceptor layer containing a bisazo compound was published in
No. 7-37543, No. 55-22834, No. 54-7
It is already known from No. 9632, No. 56-116040, etc.
ところで、有機光導電性物質を用いる公知の感光体は通
常、負帯電用として使用されている。この理由は、負帯
電使用の場合には、電荷のうちホールの移動度が大きい
ことから、光感度等の面で有利なためである。By the way, known photoreceptors using organic photoconductive substances are generally used for negative charging. The reason for this is that when negative charging is used, the mobility of holes among the charges is large, which is advantageous in terms of photosensitivity and the like.
しかしながら、このような負帯電使用の場合の問題は、
帯電器による負帯電時に雰囲気中にオゾンが発生し易く
なり、環境条件を悪くしてしまう。However, the problem with using such a negative charge is that
Ozone is likely to be generated in the atmosphere when negatively charged by the charger, worsening the environmental conditions.
また、負帯電用感光体の現像には正極性のトナーが必要
となるが、正極性のトナーは強磁性体電荷粒子に対する
摩擦帯電系列からみて製造が困難であることである。Further, a positive polarity toner is required for development of a negatively charged photoreceptor, but it is difficult to manufacture a positive polarity toner in view of the triboelectric charging sequence with respect to ferromagnetic charged particles.
そこで、有機光導電性物質を用いる感光体を正帯電で使
用する、例えば、電荷発生層上に電荷輸送層を積層し、
電荷輸送層を電子輸送能の大きい物質で形成する正帯電
感光体等が提案されている。Therefore, a photoreceptor using an organic photoconductive substance is used with positive charging, for example, a charge transport layer is laminated on a charge generation layer.
Positively charged photoreceptors and the like have been proposed in which a charge transport layer is formed of a material with a high electron transport ability.
しかしながら電荷輸送層に例えばトリニトロフルオレノ
ン等を含有せしめると、該物質が発癌性である等の問題
を提起することがある。他方、ホール輸送能の大きい電
荷輸送層上に電荷発生層を積層した正帯電感光体が考え
られるが、この機構では表面側に存在させる電荷発生層
を非常に薄くする必要があり、耐刷性等が悪くなり、実
用的な層構成ではない。However, if the charge transport layer contains, for example, trinitrofluorenone, problems may arise, such as that the substance is carcinogenic. On the other hand, a positively charged photoreceptor in which a charge generation layer is laminated on a charge transport layer with a high hole transport ability is considered, but with this mechanism, the charge generation layer on the surface side needs to be extremely thin, and printing durability may be affected. etc., and it is not a practical layer structure.
また、正帯電感光体として、米国特許３，６１５，４１
４号には、チアピリリウム塩（電荷発生物質）をポリカ
ーボネート（バインダ樹脂）と錯体を形成するよ、うに
含有させたものが示されている。しかしこの感光体では
、メモリ現象が大きく、ゴーストも発生し易いという欠
点がある。また米国特許３，３５７．９８９号には、フ
タロシアニンを含有せしめた感光体が示されているが、
フタロシアニンは結晶型によって特性が変化する上に、
結晶型を厳密に制御する必要があり、更に短波長感度が
不足しかつメモリ現象も大きく、可視光波長域の光源を
用いる複写機には不適当である。In addition, as a positively charged photoreceptor, U.S. Patent No. 3,615,41
No. 4 shows a product containing a thiapyrylium salt (charge generating substance) so as to form a complex with polycarbonate (binder resin). However, this photoreceptor has disadvantages in that the memory phenomenon is large and ghosts are likely to occur. Further, U.S. Pat. No. 3,357.989 discloses a photoreceptor containing phthalocyanine,
The properties of phthalocyanine vary depending on the crystal type, and
It is necessary to strictly control the crystal type, and furthermore, the short wavelength sensitivity is insufficient and the memory phenomenon is large, making it unsuitable for copying machines that use light sources in the visible wavelength range.
このように正帯電感光体を得るための試みが種々行なわ
れているが、いずれも光感度、メモリ現象又は労働衛生
等、また紫外線耐性、耐オゾン酸化性等の耐用性の点で
改善すべき多くの問題点がある。Various attempts have been made to obtain positively charged photoreceptors, but all of them require improvements in terms of photosensitivity, memory phenomenon, occupational hygiene, etc., and durability such as ultraviolet resistance and ozone oxidation resistance. There are many problems.
そこで機能上から光照射時ホール及び電子を発生する電
荷発生物質を含有する電荷発生層を上層（表面層）とし
、ホール輸送機能を有する電荷輸送物質を含む電荷輸送
層を下層とする積層構成の感光体を正、負両用帯電感光
体の基本形とし、足らざるを補完することが考えられる
。Therefore, from a functional standpoint, a laminated structure in which the upper layer (surface layer) is a charge generation layer containing a charge generation substance that generates holes and electrons when irradiated with light, and the lower layer is a charge transport layer containing a charge transport substance having a hole transport function. It is conceivable to make the photoreceptor the basic form of a photoreceptor for both positive and negative charging, and to supplement what is lacking.
なおかかる感光体においては、構造中に例えば電子吸引
性基を有する電荷発生物質を用いるようにすれば、感光
体表面の正電荷を打消すための電子の移動が早くなり、
高感度特性が得られることが考えられる。In addition, in such a photoreceptor, if a charge generating substance having, for example, an electron-withdrawing group is used in the structure, the movement of electrons to cancel the positive charge on the surface of the photoreceptor becomes faster.
It is thought that high sensitivity characteristics can be obtained.
しかしながら、前記正帯電感光体は電荷発生物質を含む
層が表面層として形成されるため、光照射、特に紫外線
等の短波光照射、コロナ放電、湿度、オゾン酸化、機械
的摩擦等外部作用に脆弱な電荷発生物質が直接に曝され
ることとなり、感光体の保存中及び像形成の過程で電子
写真性能が劣化し、画質が低下するようになる。However, since the positively charged photoreceptor is formed with a layer containing a charge generating substance as a surface layer, it is vulnerable to external effects such as light irradiation, especially short wave light irradiation such as ultraviolet light, corona discharge, humidity, ozone oxidation, and mechanical friction. As a result, the electrophotographic performance deteriorates during the storage of the photoreceptor and during the image formation process, resulting in a decrease in image quality.
従来の電荷輸送層を表面層とする負帯電感光体において
は、前記各種の外部作用の影響は極めて少なく、むしろ
前記電荷輸送層が下層の電荷発生層を保護する作用を有
している。In a negatively charged photoreceptor having a conventional charge transport layer as a surface layer, the effects of the various external effects described above are extremely small, and rather the charge transport layer has the effect of protecting the underlying charge generation layer.
そこで、例えば絶縁性かつ透明な樹脂から成る薄い保護
層を設け、前記電荷発生物質を含む層を外部作用から保
護することが考えられるが、光照射時発生する電荷が該
保護層でブロッキングされて光照射効果が失なわれてく
るし、また表面層となる保護層が厚い場合には感度低下
を招き、剰え紫外線遮断効果も少いので、外部作用から
の遮蔽、特に紫外線からの保護を単なる保護層だけに委
ねることはできない。Therefore, it is conceivable to provide a thin protective layer made of an insulating and transparent resin to protect the layer containing the charge-generating substance from external effects, but the protective layer may block the charges generated during light irradiation. The effect of light irradiation will be lost, and if the protective layer that forms the surface layer is thick, it will cause a decrease in sensitivity and will have little residual UV blocking effect. It cannot be left to the layers alone.
本発明の目的は、正、負帯電に適用することができ、良
好な感度を有し、耐環境性に優れ、特に紫外線耐性、耐
酸化性がよく、耐用物性のよい有機光導電性電子写真感
光体の提供にある。The object of the present invention is to provide an organic photoconductive electrophotographic material that can be applied to positive and negative charging, has good sensitivity, excellent environmental resistance, particularly has good ultraviolet resistance and oxidation resistance, and has good durability. The purpose is to provide a photoreceptor.
前記本発明の目的は、導電性支持体上に電荷発生物質（
ＣＧＭと標記）及び電荷輸送物質（ＣＴＭと標記）を含
んでなる層を有する電子写真感光体に於て、下記一般式
で表わされる化合物を含有することを特徴とする電子写
真感光体によって達成される。The object of the present invention is to provide a charge generating substance (
This is achieved by an electrophotographic photoreceptor having a layer containing a charge transport material (referred to as CGM) and a charge transport material (referred to as CTM), which is characterized by containing a compound represented by the following general formula. Ru.
Ｘはカルボニル、メチレン基を表し、Ｙは酸素原子また
はイミノ、置換イミノ基を表す。Ｂは単結合または二重
結合を表す。Ｒは水素原子ま几はヒドロキシ、アルコキ
シ、アミノ、置換アミノ、アルキル、置換カルボニルの
各基を表し、ｍはＯ〜３の整数である。X represents a carbonyl or methylene group, and Y represents an oxygen atom or an imino or substituted imino group. B represents a single bond or a double bond. R is a hydrogen atom or represents a hydroxy, alkoxy, amino, substituted amino, alkyl, or substituted carbonyl group, and m is an integer of O to 3.
本発明に係る導電性支持体上に設ける感光体層は、ＣＴ
Ｍ及びＣＧＭを混和した単層構成でもよいし、ＣＴＭを
含む層を下層としＣＧＭを含む層を上層とする複層構成
でもよし或はその逆の構成でもよい。また必要に応じて
保護層（ＯＣＬと標記）を設けてもよい。The photoreceptor layer provided on the conductive support according to the present invention is CT
It may be a single-layer structure in which M and CGM are mixed, or a multi-layer structure in which a layer containing CTM is a lower layer and a layer containing CGM is an upper layer, or vice versa. Further, a protective layer (marked as OCL) may be provided as necessary.
本発明に係る化合物は前記の少くとも一層に添加される
が感光体層表層に添加されることが好ましい。尚表層に
最も濃密に、内部にゆくに従って逓減させる形態であっ
てもよい。The compound according to the present invention is added to at least one of the above layers, but is preferably added to the surface layer of the photoreceptor layer. In addition, it may be in a form where it is most concentrated on the surface layer and gradually decreases toward the inside.
以下に本発明の詳細な説明する。The present invention will be explained in detail below.
カールソンプロセスに基く電子写真プロセスには、一般
に像露光、消去露光、転写前露光、クリーニング露光等
に紫外線を発生する光源が用いられており、該光源から
の光に含まれ、可視光に比べ大きなエネルギを有する紫
外線の繰返し照射は、感光体に用いられている有機化合
物分子を解裂させるに充分である。即ち感光体をなすＣ
ＧＭ、ＣＴＭ或はバインダ等はラジカル解離を起し本来
の分子構造を失って劣化し、従って感光体の劣化を招来
し、具体的には感度低下、残電位上昇等を惹起し、かぶ
りの発生、画質の低下に陥る。In the electrophotographic process based on the Carlson process, a light source that generates ultraviolet rays is generally used for image exposure, erasing exposure, pre-transfer exposure, cleaning exposure, etc. Repeated irradiation with energetic ultraviolet light is sufficient to cleave the organic compound molecules used in the photoreceptor. That is, C forming the photoreceptor
GM, CTM, binders, etc. undergo radical dissociation, lose their original molecular structure, and deteriorate, resulting in deterioration of the photoreceptor. Specifically, it causes a decrease in sensitivity, an increase in residual potential, etc., and the occurrence of fogging. , the image quality deteriorates.
感光体の紫外線或は紫外線及びオゾンによって誘発、派
生する複合劣化は反復して付加される各種露光処理、コ
ロナ放電によって生ずるが、露光によって発生する一重
項酸素によっても強められると考えられる。また、感光
体の層構成、ＣＧ ＭやＣＴＭの種類等によっても紫外
線等による複合劣化を受ける程度は変化するが、ＣＴＭ
の方が劣化を受は易く、特に有機光導電性物質を使用す
る場合、その影響は極めて大きい。The combined deterioration induced and derived from ultraviolet rays or ultraviolet rays and ozone in the photoreceptor is caused by various exposure treatments and corona discharge that are repeatedly applied, but it is also thought to be enhanced by singlet oxygen generated by exposure. Furthermore, the degree of combined deterioration caused by ultraviolet rays, etc. varies depending on the layer structure of the photoreceptor, the type of CGM or CTM, etc., but CTM
are more susceptible to deterioration, and the effect is particularly significant when organic photoconductive materials are used.
本発明者らは、感光体の複合劣化（特に電位低下）の改
良に関し鋭意検討の結果、感光体層中に前記一般式で示
される特定の化合物が複合劣化を著しく防止するだけで
なく、その他の電子写真特性や物理的性質の向上にも寄
与することを見出した。The inventors of the present invention have conducted intensive studies to improve the composite deterioration (particularly potential drop) of photoreceptors, and have discovered that a specific compound represented by the above general formula in the photoreceptor layer not only significantly prevents composite deterioration, but also It was also found that this contributes to improving the electrophotographic properties and physical properties of .
前記の本発明に係る化合物即ち一般に紫外線吸収剤と目
される化合物の有機物質に対する安定化機構としては、
紫外線（ＵＶと標記することがある）の保有する分解エ
ネルギがＵＶ吸収剤内で振動のエネルギに変貌すること
によると思われる。The stabilization mechanism of the compound according to the present invention, that is, a compound generally regarded as an ultraviolet absorber, against organic substances is as follows:
This is thought to be due to the fact that the decomposition energy possessed by ultraviolet light (sometimes referred to as UV) is transformed into vibrational energy within the UV absorber.
この振動のエネルギは該ＵＶ吸収剤から熱エネルギとし
て放出されるが、熱エネルギでは既に有機物質を劣化さ
せるには不充分であって、感光体は紫外線の繰返し照射
による害から保護されるものと思われる。The energy of this vibration is released as thermal energy from the UV absorber, but the thermal energy is already insufficient to degrade the organic material, and the photoreceptor is protected from harm caused by repeated UV irradiation. Seem.
以下に本発明の化合物の代表的具体例を示すが、これに
よって本発明に用いられる化合物がこれらに限定される
ものではない。Typical specific examples of the compounds of the present invention are shown below, but the compounds used in the present invention are not limited thereto.
具体的化合物
（２） ０ ５−ＯＨ，７−０ＨＣ３）
Ｎ−ＣＨ，４−ＣＨ，、７−０Ｈ（４）
ＮＨ４−ＣＨｓ＋ ７−０Ｈ（５） ＮＨ４
−Ｃｌ３．７−ＮＨ。Specific compound (2) 0 5-OH, 7-0HC3)
N-CH, 4-CH,, 7-0H (4)
NH4-CHs+ 7-0H(5) NH4
-Cl3.7-NH.
（６） ０ ４−ｃｕｓ、 ７−Ｎ（
ＣＩ（３）２（７）０７−ＯＨ
（８） ｏ ３−ＣＯＣＨｓ（１１）
ＣＩ＋３ （ｔ）−Ｃ，Ｈｓ（１
２） ＣａＨｓ 、 （ｔ） Ｃ４
Ｈ１１本発明において用いられる前記一般式で示される
化合物（以下、本発明の化合物と称する）の添加量は、
感光体の層構成、ＣＴＭの種類などによって一定ではな
いが、ＣＴＭに対して、ｏ、ｔ−ｔｏｏ重量％、好まし
くは１〜５０重量％、特に好ましくは５〜２５重量％の
範囲で用いられる。(6) 0 4-cus, 7-N(
CI(3)2(7)07-OH (8) o 3-COCHs(11)
CI+3 (t)-C,Hs(1
2) CaHs, (t)C4
H11 The amount of the compound represented by the above general formula used in the present invention (hereinafter referred to as the compound of the present invention) is:
Although it varies depending on the layer structure of the photoreceptor, the type of CTM, etc., it is used in the range of o,t-too weight%, preferably 1 to 50% by weight, particularly preferably 5 to 25% by weight, based on the CTM. .
次に本発明の感光体の構成を図面によって説明する。Next, the structure of the photoreceptor of the present invention will be explained with reference to the drawings.
本発明の感光体は例えば第１図に示すように支持体ｌ
（導電性支持体またはシート上に導電層を設けたもの）
上にＣＧＭ５と必要に応じてバインダ樹脂を含有する電
荷発生層 （以下、ＣＧＬと標記する）２を下層とし、
ＣＴＭ６と必要に応じてバインダ樹脂を含有する電荷輸
送層（以下、ＣＴＬと標記する）３を上層とする積層構
成の感光体、層４を設けたもの、第２図に示すように支
持体ｌ上にＣＴＬ３を下層とし、ＣＧＬ２を上層とする
積層構成の感光体層４を設けたもの、および第３図に示
すように支持体ｌ上にＣＧＭ、ＣＴＭおよび必要に応じ
てバインダ樹脂を含有する単層構成の感光体層４を設け
たもの等が挙げられる。The photoreceptor of the present invention has a support l as shown in FIG.
(A conductive layer provided on a conductive support or sheet)
A charge generation layer (hereinafter referred to as CGL) 2 containing CGM 5 and a binder resin as required is a lower layer,
A photoreceptor with a laminated structure consisting of CTM 6 and a charge transport layer (hereinafter referred to as CTL) 3 containing a binder resin as an upper layer, a layer 4 provided thereon, and a support l as shown in FIG. A photoreceptor layer 4 having a laminated structure with CTL3 as a lower layer and CGL2 as an upper layer is provided thereon, and as shown in FIG. Examples include those provided with a photoreceptor layer 4 having a single-layer structure.
また、第２図と同様の層構成で上層のＣＧＬにＣＧＭと
ＣＴＭの両方が含有されてもよく、該層の上に保護層（
ＯＣＬ）を設けてもよく、支持体と感光体層の間に中間
層を設けてもよい。第４図にその１例を示しである。す
なわち、支持体ｌ上に中間層７を設け、その上にＣＴＭ
６ａとバインダ樹脂を含有するＣＴＬ３およびＣＧＭ５
、ＣＴＭ６ｂおよびバインダ樹脂を含有するＣＧＬ ２
を積層した感光体層４を有し、更にバインダを主成分と
する０ＣＬ８を設けた感光体である。In addition, both CGM and CTM may be contained in the upper CGL layer with the same layer configuration as shown in FIG. 2, and a protective layer (
OCL) may be provided, and an intermediate layer may be provided between the support and the photoreceptor layer. An example is shown in FIG. That is, the intermediate layer 7 is provided on the support l, and the CTM
CTL3 and CGM5 containing 6a and binder resin
, CGL 2 containing CTM6b and binder resin
This is a photoreceptor having a photoreceptor layer 4 which is a laminated layer, and further provided with OCL8 whose main component is a binder.
本発明の化合物は、感光体を構成するＣＧＬ。The compound of the present invention is CGL that constitutes a photoreceptor.
ＣＴＬ、単層構成感光体層またはＯＣＬのいずれに含有
されてもよく、複数層に含有されてもよい。It may be contained in any of the CTL, single-layer structure photoreceptor layer, or OCL, or may be contained in multiple layers.
本発明の効果がより顕著に発揮されるのは、ＣＧＬを上
層としＣＴＬを下層とする積層構成の感光体においてで
ある。The effects of the present invention are more clearly exhibited in a photoreceptor having a laminated structure in which CGL is an upper layer and CTL is a lower layer.
次に本発明に適するＣＧＭとしては、可視光を吸収して
フリー電荷を発生するものであれば、無機顔料及び有機
顔料の何れをも用いることができる。無定形セレン、三
方晶系セレン、セレン−砒素合金、セレン−テルル合金
、硫化カドミウム、セレン化カドミウム、硫セレン化カ
ドミウム、硫化水銀、酸化鉛、硫化鉛等の無機顔料の外
、次の代表例で示されるような有機顔料が用いられる。Next, as the CGM suitable for the present invention, both inorganic pigments and organic pigments can be used as long as they absorb visible light and generate free charges. In addition to inorganic pigments such as amorphous selenium, trigonal selenium, selenium-arsenic alloy, selenium-tellurium alloy, cadmium sulfide, cadmium selenide, cadmium selenide sulfide, mercury sulfide, lead oxide, lead sulfide, the following representative examples Organic pigments such as those shown are used.
（１） モノアゾ顔料、ポリアゾ顔料、金属錯塩アゾ
顔料、ピラゾロンアゾ顔料、スチルベンアゾ及びチアゾ
ールアゾ顔料等のアゾ系顔料（２）ペリレン酸無水物及
びペリレン酸イミド等のペリレン系顔料
（３）アントラキノン誘導体、アントアントロン誘導体
、ジベンズピレンキノン誘導体、ビラントロン誘導体、
ビオラントロン誘導体及びイソビオラントロン誘導体等
のアントラキノン系又は多環キノン系顔料
、（４）インジゴ誘導体及びチオインジゴ誘導体等のイ
ンジゴイド系顔料
（５）金属フタロシアニン及び無金属フタロシアニン等
のフタロシアニン系顔料
（６） ジフェニルメタン、系顔料、トリフェニルメタ
ン顔料、キサンチン顔料及びアクリジン顔料等のカルボ
ニウム系顔料
（７）アジン顔料、オキサジン顔料及びチアジン顔料等
のキノンイミン系顔料
（８） シアニン顔料及びアゾメチン顔料等のメチン系
顔料
（９）キノリン系顔料
（ｌＯ）ニトロ系顔料
（１１）ニトロソ系顔料
（１２）ベンゾキノン及びナフトキノン系顔料（１３）
ナフタルイミド系顔料
（１４） ビスベンズイミダゾール誘導体等のペリノ
ン系顔料
前記本発明に用いられるアゾ系顔料としては、例えば次
の例示構造化合物群ＣＩ）〜〔■〕で示されるものがあ
り、該例示構造化合物群の中の個々の好ましい具体的化
合物の数例を併せ掲げる。(1) Azo pigments such as monoazo pigments, polyazo pigments, metal complex azo pigments, pyrazolone azo pigments, stilbene azo and thiazole azo pigments (2) Perylene pigments such as perylenic anhydride and perylenic acid imide (3) Anthraquinone derivatives , anthantrone derivatives, dibenzpyrenequinone derivatives, vilantrone derivatives,
Anthraquinone or polycyclic quinone pigments such as violanthrone derivatives and isoviolanthrone derivatives; (4) indigoid pigments such as indigo derivatives and thioindigo derivatives; (5) phthalocyanine pigments such as metal phthalocyanine and metal-free phthalocyanine; (6) diphenylmethane. , carbonium pigments such as triphenylmethane pigments, xanthine pigments and acridine pigments (7) Quinoneimine pigments such as azine pigments, oxazine pigments and thiazine pigments (8) Methine pigments such as cyanine pigments and azomethine pigments (9) ) Quinoline pigments (lO) Nitro pigments (11) Nitroso pigments (12) Benzoquinone and naphthoquinone pigments (13)
Naphthalimide pigments (14) Perinone pigments such as bisbenzimidazole derivatives Examples of the azo pigments used in the present invention include those shown in the following exemplary structural compound groups CI) to [■]. Several examples of specific preferred compounds in the group of structural compounds are also listed.
その好ましい具体的化合物の全容については特・５．・
（ミ］・′
例示構造化合物群〔Ｉ〕：
例示構造化合物群〔■〕：
例示構造化合物群〔■〕：
例示構造化合物群〔■〕：
例示構造化合物群〔■〕：
また、以下の多環キノン顔料から成る例示構造化合物群
（ＶＩ）〜〔■〕はＣＧＭとして最も好ま例示構造化合
物群〔■〕：
以下余白
次に本発明で使用可能なＣＴ Ｍとしては、特に制限は
ないが、例えばオキサゾール誘導体、オキサジアゾール
誘導体、チアゾール誘導体、チアジアゾール誘導体、ト
リアゾール誘導体、イミダゾール誘導体、イミダシロン
誘導体、イミダゾリジン誘導体、ビスイミダゾリジン誘
導体、スチリル化合物、ヒドラゾン化合物、ピラゾリン
誘導体、オキサシロン誘導体、ベンゾチアゾール誘導体
、ベンズイミダゾール誘導体、キナゾリン誘導体、ベン
ゾフラン誘導体、アクリジン誘導体、フェナジン誘導体
、アミノスチルベン誘導体、ポリ−Ｎ−ビニルカルバゾ
ール、ポリ−１−ビニルピレン、ポリ−９−ビニルアン
トラセン等であってよい。For a complete list of the preferred specific compounds, see Section 5.・
(Mi)・' Exemplary structural compound group [I]: Exemplary structural compound group [■]: Exemplary structural compound group [■]: Exemplary structural compound group [■]: Exemplary structural compound group [■]: In addition, the following Exemplary structural compound groups (VI) to [■] consisting of ring quinone pigments are the most preferred exemplary structural compound group [■] as CGMs. For example, oxazole derivatives, oxadiazole derivatives, thiazole derivatives, thiadiazole derivatives, triazole derivatives, imidazole derivatives, imidacilone derivatives, imidazolidine derivatives, bisimidazolidine derivatives, styryl compounds, hydrazone compounds, pyrazoline derivatives, oxacilone derivatives, benzothiazole derivatives, benz They may be imidazole derivatives, quinazoline derivatives, benzofuran derivatives, acridine derivatives, phenazine derivatives, aminostilbene derivatives, poly-N-vinylcarbazole, poly-1-vinylpyrene, poly-9-vinylanthracene, and the like.
しかしながら光照射時発生するホールの支持体側への輸
送能力が優れている外、前記ＣＧＭとの組合せに好適な
ものが好ましく用いられ、かかるＣＴＭとしては、例え
ば下記例示構造化合物群〔ＩＸ〕又は（Ｘ）で示される
スチル化合物が使用される。該例示構造化合物群中の個
々の具体的化合物の数例を併せ掲げるが、その全貌につ
いては特願昭６１ ＝１９５８８１号が参照されろ。However, in addition to its excellent ability to transport holes generated during light irradiation to the support side, those suitable for combination with the above-mentioned CGM are preferably used, and such CTMs include, for example, the following exemplary structural compound group [IX] or ( A still compound represented by X) is used. Several specific examples of individual compounds in the group of exemplified structural compounds are listed below, but please refer to Japanese Patent Application No. 195881 for the complete details.
例示構造化合物群〔■〕：
例示構造化合物群（Ｘ）
また、ＣＴＭとして下記例示構造化合物群〔刈〕〜（Ｘ
Ｖ）で示されるヒドラゾン化合物も使用可能である。向
側々の具体的化合物の全容については特願昭６１−１９
５８８１号が参照される。Exemplary structural compound group [■]: Exemplary structural compound group (X) In addition, as CTM, the following exemplary structural compound group [Kari] ~ (X
Hydrazone compounds represented by V) can also be used. For the complete details of the specific compounds on the opposite side, please refer to the patent application filed in 1986-19.
Reference is made to No. 5881.
例示構造化合物群〔■〕
例示構造化合物群（ＸＩＩ［）：
例示構造化合物群（ＸＶ）：
また、ＣＴＭとして下記例示構造化合物群〔Ｘ■〕で示
されるアミン誘導体も使用可能である。Exemplary Structural Compound Group [■] Exemplary Structural Compound Group (XII[): Exemplary Structural Compound Group (XV): In addition, amine derivatives shown in the following exemplary structural compound group [X■] can also be used as CTMs.
尚詳しくは特願昭６１−１９５８８１号が参照される。For details, refer to Japanese Patent Application No. 195881/1981.
本発明の感光体の層構成は前記のように積層構成と単層
構成とがあるが、表面層となるＣＴＬ。The layer structure of the photoreceptor of the present invention has a laminated structure and a single layer structure as described above, and CTL is used as the surface layer.
ＣＧＬ、ＯＣＬ、単層感光体層またはＯＣＬのいずれか
、もしくは複数層には感度の向上、残留電位ないし反復
使用時の疲労低減等を目的として、１種または２種以上
の電子受容性物質を含有せしめることができる。One or more electron-accepting substances may be added to CGL, OCL, single photoreceptor layer, OCL, or multiple layers for the purpose of improving sensitivity, reducing residual potential or fatigue during repeated use, etc. It can be made to contain.
本発明の感光体に使用可能な電子受容性物質としては、
例えば無水琥珀酸、無水マレイン酸、ジブロム無水マレ
イン酸、無水フタル酸、テトラクロル無水フタル酸、テ
トラブロム無水フタル酸、３−ニトロ無水フタル酸、４
−ニトロ無水フタル酸、無水ピロメリット酸、無水メリ
ット酸、テトランアノエチレン、テトラシアノキノジメ
タン、Ｏ−ジニトロベンゼン、ｍ−ジニトロベンゼン、
１，３，５．−トリニトロベンゼン、バラニトロベンゾ
ニトリル、ピクリルクロライド、キノンクロルイミド、
タロラニル、ブルマニル、２−メチルナフトキノン、ジ
クロロジシアノバラベンゾキノン、アントラキノン、ジ
ニトロアントラキノン、トリニトロフルオレノン、９−
フルオレノンデン〔ジシアノメチレンマロノジニトリル
〕、ポリニトロ−９−フルオレノンデンー〔ジシアノメ
チレンマロノジニトリル〕、ピクリン酸、フタル酸等が
挙げられる。Electron-accepting substances that can be used in the photoreceptor of the present invention include:
For example, succinic anhydride, maleic anhydride, dibromaleic anhydride, phthalic anhydride, tetrachlorophthalic anhydride, tetrabromophthalic anhydride, 3-nitrophthalic anhydride, 4
-Nitrophthalic anhydride, pyromellitic anhydride, mellitic anhydride, tetraanoethylene, tetracyanoquinodimethane, O-dinitrobenzene, m-dinitrobenzene,
1, 3, 5. - trinitrobenzene, varanitrobenzonitrile, picryl chloride, quinone chlorimide,
Talolanil, brumanil, 2-methylnaphthoquinone, dichlorodicyanobarabenzoquinone, anthraquinone, dinitroanthraquinone, trinitrofluorenone, 9-
Examples include fluorenonedine [dicyanomethylenemalonodinitrile], polynitro-9-fluorenonedine [dicyanomethylenemalonodinitrile], picric acid, phthalic acid, and the like.
本発明において感光体層に使用可能なバインダ樹脂とし
ては、例えばポリエチレン、ポリプロピレン、アクリル
樹脂、メタクリル樹脂、塩化〈ニル樹脂、酢酸ビニル樹
脂、エポキシ樹脂、ポリウレタン樹脂、フェノール樹脂
、ポリエステル樹脂、アルキッド樹脂、ポリカーボネー
ト樹脂、シリコン樹脂、メラミン樹脂等の付加重合型樹
脂、重付加型樹脂、重縮合型樹脂並びにこれらの樹脂の
繰返し単位のうちの２つ以上を含む共重合体樹脂、例え
ば塩化ビニル−酢酸ビニル共重合体樹脂、塩化ビニル−
酢酸ビニル−無水マレイン酸共重合体樹脂等の絶縁性樹
脂の他、ポリ−Ｎ−ビニルカルバゾール等の高分子有機
半導体が挙げられる。Examples of binder resins that can be used in the photoreceptor layer in the present invention include polyethylene, polypropylene, acrylic resin, methacrylic resin, <nyl chloride resin, vinyl acetate resin, epoxy resin, polyurethane resin, phenol resin, polyester resin, alkyd resin, Addition polymer resins, polyaddition resins, polycondensation resins such as polycarbonate resins, silicone resins, melamine resins, and copolymer resins containing two or more repeating units of these resins, such as vinyl chloride-vinyl acetate. Copolymer resin, vinyl chloride
In addition to insulating resins such as vinyl acetate-maleic anhydride copolymer resins, polymeric organic semiconductors such as poly-N-vinylcarbazole may be used.
また、前記中間層は接着層又はバリヤ層等として機能す
るもので、上記バインダ樹脂の外に、例えばポリビニル
アルコール、エチルセルロース、カルボキシメチルセル
ロース、塩化ビニル−酢酸ビニル共重合体、塩化ビニル
−酢酸ビニル−無水マレイン酸共重合体、カゼイン、Ｎ
−アルコキシメチル化ナイロン、澱粉等が用いられる。Further, the intermediate layer functions as an adhesive layer or a barrier layer, and in addition to the binder resin, for example, polyvinyl alcohol, ethyl cellulose, carboxymethyl cellulose, vinyl chloride-vinyl acetate copolymer, vinyl chloride-vinyl acetate-anhydrous Maleic acid copolymer, casein, N
-Alkoxymethylated nylon, starch, etc. are used.
次に前記感光体層を支持する導電性支持体としては、ア
ルミニウム、ニッケルなどの金属板、金属ドラム又は金
属箔、アルミニウム、酸化錫、酸化インジウムなどを蒸
着したプラスチックフィルムあるいは導電性物質を塗布
した祇、プラスチックなどのフィルム又はドラムを使用
することができる。Next, the conductive support supporting the photoreceptor layer may be a metal plate made of aluminum or nickel, a metal drum or metal foil, a plastic film coated with aluminum, tin oxide, indium oxide, etc., or a conductive material coated thereon. A film or drum made of plastic, etc. can be used.
ＣＧＬは既述のＣＧ Ｍを上記支持体上に真空蒸着さけ
る方法、ＣＧＭを適当な溶剤に単独らしくは適当なバイ
ンダ樹脂と共に溶解もしくは分散せしめたしのを塗布し
て乾燥させる方法により設けることができる。CGL can be provided by vacuum-depositing the above-mentioned CGM on the support, or by dissolving or dispersing CGM alone in a suitable solvent or together with a suitable binder resin, and applying and drying. can.
上記ＣＧＭを分散せしめてＣＧＬを形成する場合、当該
ＣＧＭは２μｍ以下、好ましくは１μｍ以下の平均粒径
の粉粒体とするのか好ましい。即ち、粒径があまり大き
いと層中への分散が悪くなると共に、粒子が表面に一部
突出して表面の平滑性が悪くなり、場合によつ°ては粒
子の突出部分で放電が生じたり或はそこにトナー粒子が
付着してトナーフィルミング現象が生じ易い。When CGL is formed by dispersing the above CGM, it is preferable that the CGM is a powder having an average particle size of 2 μm or less, preferably 1 μm or less. That is, if the particle size is too large, dispersion in the layer will be poor, and some of the particles will protrude from the surface, resulting in poor surface smoothness, and in some cases, electrical discharge may occur at the protruding portions of the particles. Alternatively, toner particles tend to adhere thereto, resulting in toner filming phenomenon.
ただし、上記粒径があまり小さいと却って凝集し易く、
層の抵抗が上昇したり、結晶欠陥が増えて感度及び線返
し特性が低下したり、或いは微細化する上で限界がある
から、平均粒径の下限を０．０１μｍとするのが望まし
い。However, if the above particle size is too small, it tends to aggregate,
It is desirable to set the lower limit of the average grain size to 0.01 μm because the resistance of the layer increases, the sensitivity and line return characteristics decrease due to an increase in crystal defects, or there is a limit to miniaturization.
ＣＧＬは、次の如き方法によって設けることができる。CGL can be provided by the following method.
即ち、記述のＣＧＬをボールミル、ホモミキサ等によっ
て分散媒中で微細粒子とし、バインダ樹脂を加えて混合
分散して得られる分散液を塗布する方法である。この方
法において超音波の作用下に粒子を分散させると、均一
分散が可能で′ある。That is, this is a method in which the CGL described above is made into fine particles in a dispersion medium using a ball mill, a homomixer, etc., a binder resin is added, and a dispersion obtained by mixing and dispersing is applied. By dispersing the particles under the action of ultrasound in this method, uniform dispersion is possible.
ＣＴＬの形成に用いられる溶媒としては、例えばＮ、Ｎ
−ジメチルホルムアミド、ベンゼン、トルエン、キシレ
ン、モノクロルベンゼン、ｌ、２−ジクロロエタン、ジ
クロロメタン、Ｌ、ｌ、２−トリクロロエタン、テトラ
ヒドロフラン、メチルエチルケトン、酢酸エチル、酢酸
エチル等を挙げることができろ。Examples of solvents used to form CTL include N, N
- Dimethylformamide, benzene, toluene, xylene, monochlorobenzene, 1,2-dichloroethane, dichloromethane, L,1,2-trichloroethane, tetrahydrofuran, methyl ethyl ketone, ethyl acetate, ethyl acetate, etc.
前記第１．２図及び第４図の様な機能分離層構成では、
ＣＧＬ中ＣＧＭバイング樹脂１００重量当り２０〜２０
０重量部、好ましくは２５〜１００重量部である。ＣＧ
Ｍがこれより少ないと光感度が低く、残留電位の増加を
招き、又これより多いと暗減衰が増大し、かつ受容電位
が低下する。In the functional separation layer configuration as shown in FIG. 1.2 and FIG. 4,
20-20 per 100 weight of CGM buying resin in CGL
0 parts by weight, preferably 25 to 100 parts by weight. CG
If M is less than this, the photosensitivity will be low and the residual potential will increase, and if it is more than this, dark decay will increase and the acceptance potential will decrease.
以上のようにして形成されるＣＧＬの膜厚は、正帯電用
構成の場合は好ましくは、１〜ｌＯμｍ、特に好ましく
は３〜７μｍであり、負帯電用構成の場合は好ましくは
０．０１〜１０μｍ１特に好ましくは０．１〜３μｍで
ある。The thickness of the CGL formed as described above is preferably 1 to 10 μm, particularly preferably 3 to 7 μm in the case of a positive charging configuration, and preferably 0.01 to 10 μm in the case of a negative charging configuration. 10 μm, particularly preferably 0.1 to 3 μm.
前記正帯電用構成においてはＣＧＬが表面層となるので
耐傷性に欠け、耐用性向上のためにはＣＧＬ膜厚を厚く
する必要があるが、感度低下を引き起こす。これを抑制
する手段としてＣＧＬ中へＣＴＭが添加される。この場
合のＣＧＭとＣＴＭの比はＣＧＭ１００重量部に対して
ＣＴＭ３０重量部から４００重量部である。In the configuration for positive charging, since the CGL is a surface layer, it lacks scratch resistance, and in order to improve durability, it is necessary to increase the thickness of the CGL film, but this causes a decrease in sensitivity. CTM is added to CGL as a means to suppress this. The ratio of CGM to CTM in this case is 30 to 400 parts by weight of CTM to 100 parts by weight of CGM.
しかしながら、このＣＴＭはＣＧＭに比べ複合劣化を受
は易い構造を有するので、紫外線等により容易に劣化を
受は感光体の耐久性が損なわれる。However, since this CTM has a structure that is more susceptible to complex deterioration than CGM, it is easily deteriorated by ultraviolet rays and the like, which impairs the durability of the photoreceptor.
本発明は、この悪循環を本発明の化合物の添加により解
消したものである。The present invention eliminates this vicious cycle by adding the compound of the present invention.
次に、ＣＴＬは、既述のＣＴＭを上述のＣＧＬと同様に
して （即ち、単独であるいは上述のバインダ樹脂と共
に溶解、分散せしめたものを塗布、乾燥して）形成する
ことができる。Next, the CTL can be formed by applying the above-mentioned CTM in the same manner as the above-mentioned CGL (that is, applying the CTM alone or dissolving and dispersing it together with the above-mentioned binder resin and drying).
ＣＴＬ中のＣＴＭｆｆｉはバインダ樹脂１００重量部当
り２０〜２００重量部、好ましくは３０〜１５０重量部
である。CTMffi in CTL is 20 to 200 parts by weight, preferably 30 to 150 parts by weight, per 100 parts by weight of binder resin.
ＣＴＭの含有割合がこれより少ないと光感度が悪く残留
電位が高くなり易く、又これより多いと溶媒溶解性が悪
くなる。If the CTM content is less than this, the photosensitivity will be poor and the residual potential will tend to be high, and if it is more than this, the solvent solubility will be poor.
、形成されるＣＴＬの膜厚は、好ましくは５〜５０μｍ
、特に好ましくは５〜３０μｍである。また、ＣＧＬと
ＣＴＬの膜厚比はｌ ：（１〜３０）であるのが好まし
い。The thickness of the formed CTL is preferably 5 to 50 μm.
, particularly preferably from 5 to 30 μm. Further, the film thickness ratio of CGL and CTL is preferably 1:(1 to 30).
前記第３図に示した単層構成の場合、ＣＧＭがバインダ
樹脂に含有される割合は、バインダ樹脂１００重量部に
対して２０〜２００重量部、好ましくは２５〜１００ｆ
ｆｉ量部である。In the case of the single-layer structure shown in FIG. 3, the proportion of CGM contained in the binder resin is 20 to 200 parts by weight, preferably 25 to 100 parts by weight, per 100 parts by weight of the binder resin.
fi amount part.
ＣＧＭの含有割合がこれより少ないと光感度が低く、残
留電位の増加を沼き、又これより多いと暗減衰及び受容
電位が低下する。If the content of CGM is less than this, the photosensitivity will be low and the residual potential will increase, and if it is more than this, the dark decay and reception potential will decrease.
またＣＴＭがバインダ樹脂に対して含有される割合は、
バインダ樹脂１００重量部に対して２０〜２００重量部
、好ましくは３０〜１５０重量部である。In addition, the ratio of CTM to the binder resin is
The amount is 20 to 200 parts by weight, preferably 30 to 150 parts by weight, based on 100 parts by weight of the binder resin.
ＣＴＭの含有割合がこれより少ないと光感度が悪く残留
電位が高くなり易く、又これより多いと溶媒溶解性が悪
（なる。If the content of CTM is less than this, the photosensitivity will be poor and the residual potential will tend to be high, and if it is more than this, the solvent solubility will be poor.
単層構成の場合感光体層中のＣＧＭに対するＣＴＭの量
比は重量比でｌ：３〜１：２とするのが好ましい。また
、この場合の感光体層の膜厚は７〜５０μｍ１ 好まし
くは１０〜３０μｍである。In the case of a single layer structure, the weight ratio of CTM to CGM in the photoreceptor layer is preferably 1:3 to 1:2. Further, the thickness of the photoreceptor layer in this case is 7 to 50 μm, preferably 10 to 30 μm.
本発明おいて必要に応じて設けられるＯＣＬのバインダ
として体積抵抗１０’Ωｃｍ以上、好ましくは１ｏｌＯ
Ωｃｍ以上、より好ましくは１０１３Ωｃｍ以上の透明
樹脂が用いられる。又前記バ・インクは光又は熱により
硬化する樹脂を少なくとも５０重潰％以上含有するもの
とされる。In the present invention, the OCL binder provided as necessary has a volume resistance of 10'Ωcm or more, preferably 1olO
A transparent resin having a resistance of Ωcm or more, more preferably 10 13 Ωcm or more is used. The ink contains at least 50% by weight of a resin that is cured by light or heat.
かかる光又は熱により硬化する樹脂としては、例えば熱
硬化性アクリル樹脂、シリコン樹脂、エポキシ樹脂、ウ
レタン樹脂、尿素樹脂、フェノール樹脂、ポリエステル
樹脂、アルキッド樹脂、メラミン樹脂、光硬化性の桂皮
酸樹脂等又はこれらの共重合らしくは共縮合樹脂があり
、その外電子写真材料に供される光又は熱硬化性樹脂の
全てが利用される。又前記ＣＧＬ中には加工性及び物性
の改良（亀裂防止、柔軟性付与等）を目的として必要に
より熱可塑性樹脂を５０重量％未満含有せしめることが
できる。かかる熱可塑性樹脂としては、例えばポリプロ
ピレン、アクリル樹脂、メタクリル樹脂、塩化ビニル樹
脂、酢酸ビニル樹脂、エポキシ樹脂、ブチラール樹脂、
ポリカーボネート樹脂、シリコン樹脂、又はこれらの共
重合樹脂、例えば塩化ビニル−酢酸ビニル共重合体樹脂
、塩化ビニル−酢酸ビニル−無水マレイン酸共重合体樹
脂、ポリ−Ｎ−ビニルカルバゾール等の高分子有機半導
体、その他電子写真材料に供される熱可塑性樹脂の全て
が利用される。Examples of such resins that harden with light or heat include thermosetting acrylic resins, silicone resins, epoxy resins, urethane resins, urea resins, phenol resins, polyester resins, alkyd resins, melamine resins, and photocurable cinnamic acid resins. Alternatively, copolymerization of these resins includes cocondensation resins, and all of the photo-curable or thermosetting resins used in electrophotographic materials can be used. If necessary, the CGL may contain less than 50% by weight of a thermoplastic resin for the purpose of improving processability and physical properties (preventing cracks, imparting flexibility, etc.). Examples of such thermoplastic resins include polypropylene, acrylic resin, methacrylic resin, vinyl chloride resin, vinyl acetate resin, epoxy resin, butyral resin,
Polycarbonate resins, silicone resins, or copolymer resins thereof, such as vinyl chloride-vinyl acetate copolymer resins, vinyl chloride-vinyl acetate-maleic anhydride copolymer resins, poly-N-vinylcarbazole, and other polymeric organic semiconductors , and all other thermoplastic resins used in electrophotographic materials can be used.
また前記ＯＣＬは、電子受容性物質を含有してもよく、
その他、必要によりＣＧＬを保護する目的で酸化防止剤
等を含有してもよく、前記バインダと共に溶剤に溶解さ
れ、例えばディップ塗布、スプレー塗布、ブレード塗布
、ロール塗布等により塗布・乾燥されて２μｍ以下、好
ましくは１μｍ以下の層厚に形成される。Further, the OCL may contain an electron-accepting substance,
In addition, if necessary, an antioxidant or the like may be included for the purpose of protecting CGL, which is dissolved in a solvent together with the binder, and applied and dried to a thickness of 2 μm or less by, for example, dip coating, spray coating, blade coating, roll coating, etc. , preferably with a layer thickness of 1 μm or less.
以下、本発明を実施例により説明するが、これにより本
発明の実施の態様が限定されるものではない。EXAMPLES The present invention will be explained below with reference to Examples, but the embodiments of the present invention are not limited thereby.
実施例 ｌ
アルミニウム箔をラミネートしたポリエステルフィルム
、及びアルミニウムドラムより成る導電性支持体上に、
塩化ビニル−酢酸ビニル−無水マレイン酸共重合体（エ
スレックＭＰ−１０、漬水化学工業社製）よりなる厚さ
０，１μｍの中間層を形成した。Example 1 On a conductive support consisting of a polyester film laminated with aluminum foil and an aluminum drum,
An intermediate layer having a thickness of 0.1 μm was formed from a vinyl chloride-vinyl acetate-maleic anhydride copolymer (S-LEC MP-10, manufactured by Tsukisui Kagaku Kogyo Co., Ltd.).
次いでＣＴ Ｍ （ＴＸ−７５）／ポリカーボネート樹
脂（パンライトＬ −１２５０、音大化成社製） ＝
７’５／ １００（重量比）を１６゜５重量％含有する
１、２−ジクロルエタン溶液を前記中間層上にディップ
塗布、乾燥して１５μｍ厚のＣＴＬを得た。Next, CT M (TX-75)/polycarbonate resin (Panlite L-1250, manufactured by Ondai Kasei Co., Ltd.) =
A 1,2-dichloroethane solution containing 16.5% by weight of 7'5/100 (weight ratio) was dip coated onto the intermediate layer and dried to obtain a CTL with a thickness of 15 μm.
次いで、ＣＧＭとして昇華した４、１０−ジブロモアン
スアンスロン（Ｖ［−３）／パンライトＬ−１２５０−
５０／ １００（重量比）をボールミルで２４時間粉砕
し、９重量％になるよう１．２−ジクロルエタンを加え
て更にボールミルで２４時間分散した液にＣＴＭ（ＴＸ
−７５）をパンライトＬ−１２５０に対して７５重量％
および本発明の化合物（２）をＣＴＭに対して１０重量
％加えた。この分散液にモノクロロベンゼンを加えてモ
ノクロロベンゼン／１．２−ジクロルエタン＝３／７（
体積比）になるよう調製したものをＣＴＬ上にスプレー
塗布方法により厚さ５μｍのＣＧＬを形成し、積層構成
の感光体層を有する本発明の感光体試料ｌを得た。Then, 4,10-dibromoanthrone (V[-3)/Panlite L-1250-] was sublimed as CGM.
CTM (TX
-75) in an amount of 75% by weight based on Panlite L-1250.
And the compound (2) of the present invention was added in an amount of 10% by weight based on CTM. Monochlorobenzene was added to this dispersion and monochlorobenzene/1,2-dichloroethane = 3/7 (
A CGL with a thickness of 5 μm was formed on the CTL by a spray coating method to obtain a photoreceptor sample 1 of the present invention having a laminated photoreceptor layer.
比較例（１）
ＣＧＬ中の化合物（２）を除いた以外は実施例１と同様
にして比較用の感光体試料（１）を得た。Comparative Example (1) A comparative photoreceptor sample (1) was obtained in the same manner as in Example 1 except that compound (2) in CGL was removed.
実施例 ２
実施例１における化合物（２）に代えて、化合物（５）
を添加した以外は実施例１と同様にして感光体試料２を
得た。Example 2 Compound (5) was substituted for compound (2) in Example 1.
Photoreceptor sample 2 was obtained in the same manner as in Example 1 except that .
実施例 ３
実施例１のＣＧＬから化合物（２）を除いた感光体（比
較例１の感光体に同じ）上に、熱硬化性アクリル−メラ
ミン−エポキシ（１：ｌ：１）樹脂１．５５重量部およ
び本発明の化合物（２） ０．１５５重量部をモノクロ
ロベンゼン／１，１．２−トリクロロエタン（１／１体
積比）混合溶媒１００重量部中に溶解して得られた塗布
液をスプレー塗布、乾燥して１μｍ厚のＯＣＬを形成し
、本発明の感光体試料３を得た。Example 3 On a photoreceptor (same as the photoreceptor of Comparative Example 1) obtained by removing compound (2) from the CGL of Example 1, 1.55% of thermosetting acrylic-melamine-epoxy (1:l:1) resin was applied. Spray a coating solution obtained by dissolving 0.155 parts by weight of the compound (2) of the present invention in 100 parts by weight of a mixed solvent of monochlorobenzene/1,1.2-trichloroethane (1/1 volume ratio). The coating was applied and dried to form an OCL having a thickness of 1 μm, thereby obtaining photoreceptor sample 3 of the present invention.
実施例 ４
実施例１のＣＧＬから化合物（２）を除いた感光体上に
、ンリコンハードコート用プライマＰＨ９１（東芝シリ
コン社製）を０．１μｍ厚にスプレー塗布し、更にその
上にシリコンハードコートトスガード５１０（東芝シリ
コン社製）および化合物（５）を財脂１００重量部に対
して１０重量部となるよう添加した溶液をスプレー塗布
、乾燥して１μｍｏ ＣＬを形成し、本発明の感光体試
料４を得た。Example 4 On the photoconductor obtained by removing compound (2) from the CGL of Example 1, primer PH91 (manufactured by Toshiba Silicon Co., Ltd.) for NRICON hard coat was spray-coated to a thickness of 0.1 μm, and silicone hard coat was further applied on top of the photoreceptor. A solution containing Coattos Guard 510 (manufactured by Toshiba Silicon Co., Ltd.) and compound (5) added in an amount of 10 parts by weight per 100 parts by weight of fat was spray applied and dried to form a 1 μmo CL. Body sample 4 was obtained.
実施例 ５
アルミニウム箔をラミネートしたポリエステルフィルム
、及びアルミニウムドラムより成る導電性支持体上に実
施例１と全く同様の中間層を形°成した。Example 5 An intermediate layer exactly the same as in Example 1 was formed on a conductive support consisting of a polyester film laminated with aluminum foil and an aluminum drum.
次いでＣＴＬ用塗布液としてブチラール樹脂（エスレッ
クＢ Ｘ −１、漬水化学社製）８重量％、ＣＴ Ｍ
（ＩＸ −７５） ６重量％となるようメチルエチルケ
トンに溶解して得られる溶液を前記中間層上に塗布、乾
燥して１０μｍ厚のＣＴＬを形成した。Next, as a coating liquid for CTL, 8% by weight of butyral resin (S-LEC B
(IX-75) A solution obtained by dissolving 6% by weight in methyl ethyl ketone was applied onto the intermediate layer and dried to form a 10 μm thick CTL.
次いでＣＧ Ｍ（Ｉｔ／ −７）０．２ｙをペイントコ
ンデショナ（Ｐａｉｎｔ Ｃｏｎｄｉｔｉｏｎｅｒ、
Ｒｅｄ Ｄｅｖｉ１社製）で３０分粉砕し、これにポリ
カーボネート樹脂（パンライトＬ−１２５０、前出）を
１．２−ジクロロエタン／１，１．２−トリクロロエタ
ン混合溶媒に０．５重量％となるよう溶解させた溶液を
８．３９加えて３分間分散した後、これにポリカーボネ
ート樹脂３、ＣＴＭ （ＩＸ−７５）および化合物（
２）を、それぞれ３．３重１％、２．６重量％および０
．２６重量％となるよう１．２−ジクロロエタン／１，
１．２−トリクロロエタン混合溶媒に溶解して得られる
溶液１９．１９を加えて更に３００分間分散た。Next, apply CG M (It/-7) 0.2y to a paint conditioner.
(manufactured by Red Devi 1) for 30 minutes, and polycarbonate resin (Panlite L-1250, mentioned above) was added to this in a mixed solvent of 1,2-dichloroethane/1,1,2-trichloroethane to a concentration of 0.5% by weight. After adding 8.39% of the dissolved solution and dispersing for 3 minutes, polycarbonate resin 3, CTM (IX-75) and compound (
2), 3.3% by weight, 2.6% by weight and 0% by weight, respectively.
．． 1,2-dichloroethane/1, so as to be 26% by weight.
A solution 19.19 obtained by dissolving in a 1.2-trichloroethane mixed solvent was added and further dispersed for 300 minutes.
かくして得られた分散液を前記ＣＴＬ上にスプレー塗布
し、かつ乾燥して５μｍ厚のＣＧＬを形成し、積層構成
の感光体層を有する本発明の態様の感光体試料５を得た
。The thus obtained dispersion was spray-coated onto the CTL and dried to form a CGL with a thickness of 5 μm, thereby obtaining photoreceptor sample 5 of the embodiment of the present invention having photoreceptor layers having a laminated structure.
比較例 （２）
ＣＧＬ中の化合物（２）を除いた以外は実施例５と同様
にして比較用の感光体試料（２）を得た。Comparative Example (2) A comparative photoreceptor sample (2) was obtained in the same manner as in Example 5 except that compound (2) in CGL was removed.
実施例 ６
実施例５における化合物（２）に代えて、化合物（５）
を添加した以外は実施例５と同様にして本発明の感光体
６を得た。Example 6 Compound (5) was substituted for compound (2) in Example 5.
Photoreceptor 6 of the present invention was obtained in the same manner as in Example 5 except that .
実施例 ７
実施例５のＣＧＬから化合物（２）を除いた感光体（比
較例２の感光体に同じ）上に、実施例３に用いた化合物
（２）を含有するＯＣＬを設け、本発明の感光体７を得
た。Example 7 OCL containing the compound (2) used in Example 3 was provided on a photoreceptor (same as the photoreceptor of Comparative Example 2) obtained by removing compound (2) from the CGL of Example 5, and the present invention A photoreceptor 7 was obtained.
実施例 ８
実施例５のＣＧＬから化合物（２）を除いた感光体上に
、実施例７に用いた化合物（２）を含有するＯＣＬを設
け、本発明の感光体８を得た。Example 8 OCL containing the compound (2) used in Example 7 was provided on a photoreceptor obtained by removing compound (2) from the CGL of Example 5 to obtain photoreceptor 8 of the present invention.
実施例 ９
アルミニウム箔をラミネートしたポリエステルフィルム
、及びアルミニウムドラム上に、実施例１と全く同様の
中間層を形成した。Example 9 An intermediate layer exactly the same as in Example 1 was formed on a polyester film laminated with aluminum foil and an aluminum drum.
次いで昇華した４、１０−ジブロモアンスアンスロン（
■−３）４０ｇを磁製ボールミルにて４Ｏｒｐｍで２４
時間粉砕し、パンライトＬ−１２５０、（前出）２０ｇ
と１．２−ジクロロエタン１３００＋＋ｌを加え、更に
２４時間分散してＣＧＬ用塗布液とした。これを前記中
間層上に塗布し膜厚１μｍのＣＧＬを設けた。Then sublimed 4,10-dibromoanthrone (
■-3) 40g in a porcelain ball mill at 4Orpm for 24 hours
Pulverized for a while, Panlite L-1250, (mentioned above) 20g
and 1,300++ liters of 1,2-dichloroethane were added, and the mixture was further dispersed for 24 hours to obtain a CGL coating solution. This was applied onto the intermediate layer to form a CGL having a thickness of 1 μm.
次いでＣＴ Ｍ （ＬＸ −６１）７．５ｇ、パンライ
トＬ−１２５０，１０９および化合物（２）０．７５９
を、１．２−ジクロロエタン３０ｍ＋！に溶解した溶液
を前記ＣＧＬに塗布して膜厚１５μｍのＣＴＬを形成し
、本発明の感光体９を作成した。Then CT M (LX-61) 7.5 g, Panlite L-1250,109 and compound (2) 0.759
, 1,2-dichloroethane 30m+! A solution dissolved in the above was applied to the CGL to form a CTL having a film thickness of 15 μm, thereby producing the photoreceptor 9 of the present invention.
比較例 （３）
ＣＴＬ中の化合物（２）を除いた以外は実施例つと同様
にして比較用の感光体（３）を得た。Comparative Example (3) A comparative photoreceptor (3) was obtained in the same manner as in Example 1 except that compound (2) in the CTL was removed.
実施例１０
アルミニウム箔をラミネー１− したポリエステルフィ
ルム及びアルミニウムドラムから成る導電性支持体上に
、実施例１と全く同様の中間層を形成した。Example 10 An intermediate layer exactly the same as in Example 1 was formed on a conductive support consisting of a polyester film laminated with aluminum foil and an aluminum drum.
次いでＣＧＬとしてビスアゾ化合物（■−７Ｎ、５ｇを
１．２−ジクロロエタン／モノエタノールアミン（１０
００／ １体積比）混合溶媒１００ ｍ ｌ中にボール
ミルで８時間分散させた分散液を上記中間層上に塗布し
、充分乾燥して０．３ｇ厚のＣＧＬを設けた。Then, as CGL, 5 g of bisazo compound (■-7N) was mixed with 1,2-dichloroethane/monoethanolamine (10
A dispersion liquid was dispersed in 100 ml of a mixed solvent (volume ratio: 00/1) for 8 hours using a ball mill, and then applied onto the above intermediate layer and sufficiently dried to provide a CGL with a thickness of 0.3 g.
次いでＣＴＭとしてスチリル化合物（ＩＸ−４３）１１
．２５ｇ、パンライ１． Ｌ−１２５０（前出）１５ｇ
および（ヒ合物（２＞１．１２５ｇを１，２−ジクロロ
エタン１００ｍ１に溶解した溶液を前記ＣＧＬ上に塗布
し、充分乾燥して１５μ…厚のＣＴＬを形成し、本発明
の感光体１０を作成した。Then styryl compound (IX-43) 11 as CTM
．． 25g, Panrai 1. L-1250 (mentioned above) 15g
A solution of H compound (2>1.125 g dissolved in 100 ml of 1,2-dichloroethane) is coated on the CGL and sufficiently dried to form a CTL with a thickness of 15 μm. Created.
比較例 （４）
ＣＴＬ中の化合物（２）を除いた以外は、実施例１０と
同様にして比較用の感光体（４）を作成した。Comparative Example (4) A comparative photoreceptor (4) was prepared in the same manner as in Example 10 except that compound (2) in the CTL was removed.
前記実施例試料１−１０及び比較例試料（１）〜（４）
についてＵＶ耐性について、帯電性に対する２万回の実
写テスト及びＵＶ曝射による感度変化の定量的測定を行
った。The above Example Samples 1-10 and Comparative Example Samples (1) to (4)
Regarding UV resistance, we conducted a 20,000-shot photo test on chargeability and quantitatively measured changes in sensitivity due to UV exposure.
帯電性実写テストは、Ｕ−Ｂ ｉｘ ２８１２ ＭＲ（
小西六写真工業（株）製）の改造実験機に試料感光体ド
ラムを装着し、正または負帯電させ、前記感光体に対す
る像露光をはじめとする各工程及び定着からなる単位サ
イクルを２万回繰返し、実写テスト初期の正、負帯電電
位を±ｖ、、２万回終了後回終了後帯電電位を±Ｖ、と
する。The chargeability live-action test was conducted using U-Bix 2812 MR (
A sample photoreceptor drum was attached to a modified experimental machine manufactured by Konishiroku Photo Industry Co., Ltd., and the sample photoreceptor drum was charged positively or negatively, and a unit cycle consisting of each process including image exposure and fixing on the photoreceptor was performed 20,000 times. It is assumed that the positive and negative charging potentials at the initial stage of the repeated live-action test are ±V, and after 20,000 repetitions, the charging potential after the completion of the test is ±V.
またＵＶ曝射による感度変化は、既知強度の紫外線を試
料フィルムを断裁した感光体シートに照射し、その照射
前後に於て、十または一６００■に帯電させた該感光体
の電位を夫々±１００Ｖにまで庸す露光量Ｅ’：：：を
用いて求めた。Changes in sensitivity due to UV exposure can be determined by irradiating ultraviolet rays of known intensity onto a photoreceptor sheet obtained by cutting a sample film, and before and after the irradiation, the potential of the photoreceptor, which has been charged to 10 or 1600 cm, is adjusted to ± It was determined using the exposure amount E'::: which extends to 100V.
感光体の感度ＳはＥ”’ＯＣＩ／Ｓの関係として定義さ
れ、Ｅτ■が小さいほど感度Ｓは大きく硬調な画像かえ
られる。The sensitivity S of the photoreceptor is defined as the relationship E'''OCI/S, and the smaller Eτ■, the greater the sensitivity S and the higher the contrast of the image.
ＵＶ曝射前後の感度を夫々Ｓ、、Ｓ、とすれば、その逆
数比Ｒｓ；（１／ Ｓ ＋）／ （１／ Ｓ ｏ）−Ｓ
ｏ／ Ｓ ＋はＵＶ耐性を表し、Ｒｓが大きいほどＵ
Ｖ耐性があることになる。If the sensitivities before and after UV exposure are S, S, respectively, then the reciprocal ratio Rs; (1/S +)/(1/S o) - S
o/S+ represents UV resistance, and the larger Rs is, the more U
This means that it is resistant to V.
ＵＶ照射は理化学用水銀ランプＳ ＨＬ −１００Ｕ
Ｖ−２（（株）東芝製）を用い試料の感光体シートを３
０ｃｍの距離に置き他の電磁波を遮断しＵＶ強度１５０
０ｃｄ／ｍ”で１００分間照射を行い、感度測定は静電
試験機（川口電機製作所；５ｐ−４２８型）によった。UV irradiation is done using a physical and chemical mercury lamp S HL-100U
Using V-2 (manufactured by Toshiba Corporation), the sample photoreceptor sheet was
Placed at a distance of 0cm to block other electromagnetic waves and UV intensity 150
Irradiation was performed for 100 minutes at 0 cd/m'', and the sensitivity was measured using an electrostatic tester (Kawaguchi Electric Seisakusho; Model 5p-428).
これらの結果を第１表に示す。These results are shown in Table 1.
第１表
註；括弧を付した試料Ｎｏ、は比絞試料第１表からも明
らかなように、本発明の化合物を添加することにより、
紫外線照射下におけるコロナ帯電での電位低下が著しく
改善される。しかも、本発明の化合物の添加により、感
度低下も殆どないことが判る。Note to Table 1: Sample numbers in parentheses are specific samples.As is clear from Table 1, by adding the compound of the present invention,
Potential drop due to corona charging under ultraviolet irradiation is significantly improved. Furthermore, it can be seen that there is almost no decrease in sensitivity due to the addition of the compound of the present invention.
第１図〜第４図は本発明の感光体の断面図である。 ｌ・・・支持体 ２・・・電荷発生層（ＣＧＬ） ３・・・電荷輸送層（ＣＴＬ） ４・・・感光層 ５・・・電荷発生物質（ＣＧＭ） ６・・・電荷輸送物質（ＣＴＭ） ７・・・中間層 ８・・・保護層（ＯＣＬ） 1 to 4 are cross-sectional views of the photoreceptor of the present invention. l...Support 2... Charge generation layer (CGL) 3...Charge transport layer (CTL) 4...Photosensitive layer 5... Charge generating material (CGM) 6...Charge transport material (CTM) 7...middle class 8...Protective layer (OCL)
Claims (1)
でなる層を有する電子写真感光体に於て、下記一般式で
表される化合物を含有することを特徴とする電子写真感
光体。 一般式 ▲数式、化学式、表等があります▼ 〔Ｘはカルボニル、メチレン基を表し、Ｙは酸素原子ま
たはイミノ、置換イミノ基を表す。Ｂは単結合または二
重結合を表す。Ｒは水素原子またはヒドロキシ、アルコ
キシ、アミノ、置換アミノ、アルキル、置換カルボニル
の各基を表し、ｍは０〜３の整数である。〕[Scope of Claims] An electrophotographic photoreceptor having a layer containing a charge-generating substance and a charge-transporting substance on a conductive support, characterized by containing a compound represented by the following general formula. Electrophotographic photoreceptor. General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [X represents carbonyl or methylene group, Y represents oxygen atom or imino or substituted imino group. B represents a single bond or a double bond. R represents a hydrogen atom or a hydroxy, alkoxy, amino, substituted amino, alkyl, or substituted carbonyl group, and m is an integer of 0 to 3. ]
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP31384586A JPS63159860A (en) | 1986-12-23 | 1986-12-23 | Electrophotographic sensitive body |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP31384586A JPS63159860A (en) | 1986-12-23 | 1986-12-23 | Electrophotographic sensitive body |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63159860A true JPS63159860A (en) | 1988-07-02 |
| JPH0582937B2 JPH0582937B2 (en) | 1993-11-24 |
Family
ID=18046200
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP31384586A Granted JPS63159860A (en) | 1986-12-23 | 1986-12-23 | Electrophotographic sensitive body |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63159860A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5294510A (en) * | 1990-06-14 | 1994-03-15 | Minolta Camera Kabushiki Kaisha | Photosensitive member containing specific coumarin fluorescent bleaching agent |
| EP2402819A1 (en) * | 2010-06-30 | 2012-01-04 | Canon Kabushiki Kaisha | Electrophotographic photosensitive member, process cartridge and electrophotographic apparatus |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61156052A (en) * | 1984-12-24 | 1986-07-15 | ゼロツクス コーポレーシヨン | Photoconductive image forming material |
| JPS61156131A (en) * | 1984-12-24 | 1986-07-15 | ゼロツクス コーポレーシヨン | Photoconductive image forming material |
-
1986
- 1986-12-23 JP JP31384586A patent/JPS63159860A/en active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61156052A (en) * | 1984-12-24 | 1986-07-15 | ゼロツクス コーポレーシヨン | Photoconductive image forming material |
| JPS61156131A (en) * | 1984-12-24 | 1986-07-15 | ゼロツクス コーポレーシヨン | Photoconductive image forming material |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5294510A (en) * | 1990-06-14 | 1994-03-15 | Minolta Camera Kabushiki Kaisha | Photosensitive member containing specific coumarin fluorescent bleaching agent |
| EP2402819A1 (en) * | 2010-06-30 | 2012-01-04 | Canon Kabushiki Kaisha | Electrophotographic photosensitive member, process cartridge and electrophotographic apparatus |
| US8415078B2 (en) | 2010-06-30 | 2013-04-09 | Canon Kabushiki Kaisha | Electrophotographic photosensitive member, process electrophotographic apparatus |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0582937B2 (en) | 1993-11-24 |
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