JPH0253066A - Photosensitive body - Google Patents
Photosensitive bodyInfo
- Publication number
- JPH0253066A JPH0253066A JP20432788A JP20432788A JPH0253066A JP H0253066 A JPH0253066 A JP H0253066A JP 20432788 A JP20432788 A JP 20432788A JP 20432788 A JP20432788 A JP 20432788A JP H0253066 A JPH0253066 A JP H0253066A
- Authority
- JP
- Japan
- Prior art keywords
- group
- carrier
- layer
- weight
- substance
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000000463 material Substances 0.000 claims abstract description 16
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
- 125000003118 aryl group Chemical group 0.000 claims abstract description 5
- 125000004957 naphthylene group Chemical group 0.000 claims abstract description 5
- 125000000732 arylene group Chemical group 0.000 claims abstract description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 4
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims abstract description 3
- 239000000126 substance Substances 0.000 claims description 62
- 150000001875 compounds Chemical class 0.000 claims description 30
- 230000035945 sensitivity Effects 0.000 abstract description 15
- 230000007423 decrease Effects 0.000 abstract description 5
- 230000006866 deterioration Effects 0.000 abstract description 3
- 238000012546 transfer Methods 0.000 abstract description 2
- 230000003252 repetitive effect Effects 0.000 abstract 2
- 239000010410 layer Substances 0.000 description 78
- 108091008695 photoreceptors Proteins 0.000 description 58
- 239000000049 pigment Substances 0.000 description 31
- 239000011230 binding agent Substances 0.000 description 11
- 238000000034 method Methods 0.000 description 8
- -1 0-dinitrobenzene Chemical compound 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 229910052782 aluminium Inorganic materials 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 239000011241 protective layer Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229910052711 selenium Inorganic materials 0.000 description 4
- 239000011669 selenium Substances 0.000 description 4
- WDCYWAQPCXBPJA-UHFFFAOYSA-N 1,3-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC([N+]([O-])=O)=C1 WDCYWAQPCXBPJA-UHFFFAOYSA-N 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 3
- WUPHOULIZUERAE-UHFFFAOYSA-N 3-(oxolan-2-yl)propanoic acid Chemical compound OC(=O)CCC1CCCO1 WUPHOULIZUERAE-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000000996 additive effect Effects 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
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 229910052980 cadmium sulfide Inorganic materials 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229920005668 polycarbonate resin Polymers 0.000 description 3
- 239000004431 polycarbonate resin Substances 0.000 description 3
- 229920006267 polyester film Polymers 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-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
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000004419 Panlite Substances 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- UATJOMSPNYCXIX-UHFFFAOYSA-N Trinitrobenzene Chemical compound [O-][N+](=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 UATJOMSPNYCXIX-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid 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
- 239000012790 adhesive layer Substances 0.000 description 2
- 229920000180 alkyd Polymers 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 239000010419 fine particle Substances 0.000 description 2
- 239000011888 foil Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 150000003949 imides Chemical class 0.000 description 2
- 239000001023 inorganic pigment Substances 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
- YDSWCNNOKPMOTP-UHFFFAOYSA-N mellitic acid Chemical compound OC(=O)C1=C(C(O)=O)C(C(O)=O)=C(C(O)=O)C(C(O)=O)=C1C(O)=O YDSWCNNOKPMOTP-UHFFFAOYSA-N 0.000 description 2
- 239000012860 organic pigment Substances 0.000 description 2
- 229920001568 phenolic resin Polymers 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 239000002985 plastic film Substances 0.000 description 2
- 229920006255 plastic film Polymers 0.000 description 2
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 2
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 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 2
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 2
- 229910052721 tungsten Inorganic materials 0.000 description 2
- 239000010937 tungsten Substances 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 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
- XVMIKRZPDSXBTP-UHFFFAOYSA-N 1,3-dibromobutan-2-one Chemical compound CC(Br)C(=O)CBr XVMIKRZPDSXBTP-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
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- XQGDNRFLRLSUFQ-UHFFFAOYSA-N 2H-pyranthren-1-one Chemical class C1=C(C2=C3C4=C56)C=CC3=CC5=C3C=CC=CC3=CC6=CC=C4C=C2C2=C1C(=O)CC=C2 XQGDNRFLRLSUFQ-UHFFFAOYSA-N 0.000 description 1
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 1
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 description 1
- UKYNESNNFCHAEV-UHFFFAOYSA-N 3,4-dibromooxolane-2,5-dione Chemical compound BrC1C(Br)C(=O)OC1=O UKYNESNNFCHAEV-UHFFFAOYSA-N 0.000 description 1
- ITUYMTWJWYTELW-UHFFFAOYSA-N 4-chloroiminocyclohexa-2,5-dien-1-one Chemical compound ClN=C1C=CC(=O)C=C1 ITUYMTWJWYTELW-UHFFFAOYSA-N 0.000 description 1
- ROFZMKDROVBLNY-UHFFFAOYSA-N 4-nitro-2-benzofuran-1,3-dione Chemical compound [O-][N+](=O)C1=CC=CC2=C1C(=O)OC2=O ROFZMKDROVBLNY-UHFFFAOYSA-N 0.000 description 1
- OTLNPYWUJOZPPA-UHFFFAOYSA-N 4-nitrobenzoic acid Chemical compound OC(=O)C1=CC=C([N+]([O-])=O)C=C1 OTLNPYWUJOZPPA-UHFFFAOYSA-N 0.000 description 1
- NKJIFDNZPGLLSH-UHFFFAOYSA-N 4-nitrobenzonitrile Chemical compound [O-][N+](=O)C1=CC=C(C#N)C=C1 NKJIFDNZPGLLSH-UHFFFAOYSA-N 0.000 description 1
- MMVIDXVHQANYAE-UHFFFAOYSA-N 5-nitro-2-benzofuran-1,3-dione Chemical compound [O-][N+](=O)C1=CC=C2C(=O)OC(=O)C2=C1 MMVIDXVHQANYAE-UHFFFAOYSA-N 0.000 description 1
- MEXUTNIFSHFQRG-UHFFFAOYSA-N 6,7,12,13-tetrahydro-5h-indolo[2,3-a]pyrrolo[3,4-c]carbazol-5-one Chemical compound C12=C3C=CC=C[C]3NC2=C2NC3=CC=C[CH]C3=C2C2=C1C(=O)NC2 MEXUTNIFSHFQRG-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 229910000967 As alloy Inorganic materials 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- 235000000177 Indigofera tinctoria Nutrition 0.000 description 1
- 229930192627 Naphthoquinone Natural products 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- 229920007962 Styrene Methyl Methacrylate Polymers 0.000 description 1
- 229910001215 Te alloy Inorganic materials 0.000 description 1
- QHWKHLYUUZGSCW-UHFFFAOYSA-N Tetrabromophthalic anhydride Chemical compound BrC1=C(Br)C(Br)=C2C(=O)OC(=O)C2=C1Br QHWKHLYUUZGSCW-UHFFFAOYSA-N 0.000 description 1
- ZTWQZJLUUZHJGS-UHFFFAOYSA-N Vat Yellow 4 Chemical class C12=CC=CC=C2C(=O)C2=CC=C3C4=CC=CC=C4C(=O)C4=C3C2=C1C=C4 ZTWQZJLUUZHJGS-UHFFFAOYSA-N 0.000 description 1
- 229920002433 Vinyl chloride-vinyl acetate copolymer Polymers 0.000 description 1
- QLNFINLXAKOTJB-UHFFFAOYSA-N [As].[Se] Chemical compound [As].[Se] QLNFINLXAKOTJB-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- XJHABGPPCLHLLV-UHFFFAOYSA-N benzo[de]isoquinoline-1,3-dione Chemical compound C1=CC(C(=O)NC2=O)=C3C2=CC=CC3=C1 XJHABGPPCLHLLV-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- UIZLQMLDSWKZGC-UHFFFAOYSA-N cadmium helium Chemical compound [He].[Cd] UIZLQMLDSWKZGC-UHFFFAOYSA-N 0.000 description 1
- UHYPYGJEEGLRJD-UHFFFAOYSA-N cadmium(2+);selenium(2-) Chemical compound [Se-2].[Cd+2] UHYPYGJEEGLRJD-UHFFFAOYSA-N 0.000 description 1
- JLATXDOZXBEBJX-UHFFFAOYSA-N cadmium(2+);selenium(2-);sulfide Chemical compound [S-2].[Se-2].[Cd+2].[Cd+2] JLATXDOZXBEBJX-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000005626 carbonium group Chemical group 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
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- 239000000969 carrier Substances 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- QJNYIFMVIUOUSU-UHFFFAOYSA-N chloroethene;ethenyl acetate;furan-2,5-dione Chemical compound ClC=C.CC(=O)OC=C.O=C1OC(=O)C=C1 QJNYIFMVIUOUSU-UHFFFAOYSA-N 0.000 description 1
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- 239000012792 core layer Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
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- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 125000004915 dibutylamino group Chemical group C(CCC)N(CCCC)* 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 125000004914 dipropylamino group Chemical group C(CC)N(CCC)* 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
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- 150000008376 fluorenones Chemical class 0.000 description 1
- VOOLKNUJNPZAHE-UHFFFAOYSA-N formaldehyde;2-methylphenol Chemical compound O=C.CC1=CC=CC=C1O VOOLKNUJNPZAHE-UHFFFAOYSA-N 0.000 description 1
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- CPBQJMYROZQQJC-UHFFFAOYSA-N helium neon Chemical compound [He].[Ne] CPBQJMYROZQQJC-UHFFFAOYSA-N 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 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
- 238000003475 lamination Methods 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
- 239000007788 liquid 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
- 238000005259 measurement Methods 0.000 description 1
- 239000002609 medium Substances 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
- 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
- 239000000113 methacrylic resin Substances 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- ADFPJHOAARPYLP-UHFFFAOYSA-N methyl 2-methylprop-2-enoate;styrene Chemical compound COC(=O)C(C)=C.C=CC1=CC=CC=C1 ADFPJHOAARPYLP-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 125000001624 naphthyl group Chemical group 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
- YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 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
- 239000005011 phenolic resin Substances 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 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
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 150000004060 quinone imines Chemical class 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 125000000547 substituted alkyl 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
- 238000001308 synthesis method Methods 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- 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
- NLDYACGHTUPAQU-UHFFFAOYSA-N tetracyanoethylene Chemical group N#CC(C#N)=C(C#N)C#N NLDYACGHTUPAQU-UHFFFAOYSA-N 0.000 description 1
- PCCVSPMFGIFTHU-UHFFFAOYSA-N tetracyanoquinodimethane Chemical compound N#CC(C#N)=C1C=CC(=C(C#N)C#N)C=C1 PCCVSPMFGIFTHU-UHFFFAOYSA-N 0.000 description 1
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 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
- 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
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
- G03G5/0664—Dyes
- G03G5/0666—Dyes containing a methine or polymethine group
- G03G5/0672—Dyes containing a methine or polymethine group containing two or more methine or polymethine 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
- G03G5/0664—Dyes
- G03G5/0666—Dyes containing a methine or polymethine group
- G03G5/0668—Dyes containing a methine or polymethine group containing only one methine or polymethine group
Abstract
Description
【発明の詳細な説明】
イ、産業上の利用分野
本発明は感光体、例えば電子写真感光体に関するもので
ある。DETAILED DESCRIPTION OF THE INVENTION A. Field of Industrial Application The present invention relates to a photoreceptor, such as an electrophotographic photoreceptor.
口、従来技術
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化合物を主成分とする感光
層を有する無機感光体が広く用いられてきた。しかしこ
れらは、感度、熱安定性、耐湿性、耐久性等において必
ずしも満足し得るものではなかった0例えばセレンは、
結晶化すると電子写真感光体としての特性が低下してし
まうため製造上も難しく、また熱や指紋等が原因となり
結晶化し、電子写真感光体としての特性が低下してしま
う。また硫化カドミウムや酸化亜鉛では、耐湿性や耐久
性に問題があった。BACKGROUND ART Conventionally, inorganic photoreceptors having a photosensitive layer containing an inorganic photoconductive compound such as selenium, zinc oxide, or cadmium sulfide as a main component have been widely used as electrophotographic photoreceptors. However, these were not always satisfactory in terms of sensitivity, thermal stability, moisture resistance, durability, etc.For example, selenium
Crystallization deteriorates the properties as an electrophotographic photoreceptor, making it difficult to manufacture, and crystallization occurs due to heat, fingerprints, etc., resulting in a reduction in the properties as an electrophotographic photoreceptor. Additionally, cadmium sulfide and zinc oxide have problems with moisture resistance and durability.
これら無機感光体の持つ欠点を克服する目的で、様々な
有機光導電性化合物を主成分とする感光層を有する有機
感光体の研究開発が近年盛んに行われている。In order to overcome these drawbacks of inorganic photoreceptors, research and development of organic photoreceptors having photosensitive layers mainly composed of various organic photoconductive compounds has been actively conducted in recent years.
例えば、特公昭50−10496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
レノンを含有する感光層で構成した有機感光体の記載が
ある。しかしこの感光体は、感度および耐久性において
、必ずしも満足できるものではなかった。For example, Japanese Patent Publication No. 50-10496 describes an organic photoreceptor comprising a photosensitive layer containing poly-N-vinylcarbazole and 2,4,7-dolinitro-9-fluorenone. However, this photoreceptor was not necessarily satisfactory in terms of sensitivity and durability.
この様な欠点を改良するために、キャリア発生機能とキ
ャリア輸送機能とを異なる物質に分担させ高性能の有機
感光体を開発する試みがなされている。この様ないわゆ
る機能分離型の電子写真感光体は、各々の材料を広い範
囲から選択することができ、任意の性能を有する電子写
真感光体を比較的容易に作成し得ることから多くの研究
がなされてきた。In order to improve these drawbacks, attempts have been made to develop a high-performance organic photoreceptor in which the carrier generation function and the carrier transport function are shared by different substances. Many studies have been conducted on such so-called functionally separated electrophotographic photoreceptors because each material can be selected from a wide range and an electrophotographic photoreceptor with arbitrary performance can be produced relatively easily. It has been done.
その結果キャリア発生物質として、各種のアゾ化合物が
開発され実用に供されている。一方、キャリア輸送物質
についても、例えば、特開昭51−94829号、同5
2−4242号、同52−72231号、同53270
33号、同55−52063号、同58−65440号
、同58−1198425号、同60−196768号
等に開示されている如く、多岐にわたる物質が提案され
ている。As a result, various azo compounds have been developed and put into practical use as carrier-generating substances. On the other hand, regarding carrier transport substances, for example, JP-A-51-94829;
No. 2-4242, No. 52-72231, No. 53270
A wide variety of substances have been proposed, as disclosed in No. 33, No. 55-52063, No. 58-65440, No. 58-1198425, No. 60-196768, etc.
ここで、以下のような問題点の解決が要請されている。 Here, solutions to the following problems are required.
(a)、前記の如きキャリア輸送物質を使用した電子写
真感光体には、比較的優れた電子写真性能を示すものも
あるが、光、オゾンあるいは電気的負荷に対する耐久性
が弱く、繰り返し使用時において性能が不安定で劣化等
を生じるため実用上の要求を十分満足させるものではな
く、更に優れたキャリア輸送機能を有し、かつ長期間の
使用に対して安定した性能を示すキャリア輸送物質の開
発が望まれていた。(a) Some electrophotographic photoreceptors using carrier transport materials as described above exhibit relatively excellent electrophotographic performance, but they have poor durability against light, ozone, or electrical loads, and when used repeatedly. However, it does not fully satisfy practical requirements because its performance is unstable and causes deterioration, etc., and it is necessary to develop carrier transport materials that have even better carrier transport functions and exhibit stable performance over long periods of use. development was desired.
(b)、有機感光体をより高速で複写のできる電子写真
複写機に搭載する要請は近年益々高まりつつあり、より
高感度、より高耐久性の感光体の開発が望まれていた。(b) In recent years, the demand for incorporating organic photoreceptors into electrophotographic copying machines capable of copying at higher speeds has been increasing, and the development of photoreceptors with higher sensitivity and higher durability has been desired.
一般にキャリア輸送層中のキャリア輸送物質は結着剤1
00重量部に対し60重量部から100重量部の範囲で
用いられることが多い、これは、キャリアの輸送には、
キャリア輸送物質の分子間距離が重要な意味を持ってい
るためである。すなわちキャリア輸送物質の濃度がこれ
以下になるとキャリア輸送物質の分子間距離が大きくな
り、キャリアの輸送が困難となりその結果感度の低下が
著しく太き(なるためである。Generally, the carrier transport substance in the carrier transport layer is a binder 1
It is often used in the range of 60 parts by weight to 100 parts by weight per 00 parts by weight.
This is because the intermolecular distance of the carrier transport substance has an important meaning. That is, if the concentration of the carrier transporting substance is below this level, the distance between the molecules of the carrier transporting substance becomes large, making it difficult to transport carriers, and as a result, the sensitivity decreases significantly.
反面、耐久性の面から考えると、キャリア輸送層中のキ
ャリア輸送物質の濃度が低い方がキャリア輸送層の被膜
強度が強くなり、傷が付きにくく、また長期間の使用に
際しても、クリーニングブレードや磁気ブラシによる表
面の摩擦が少なく、極めて耐久性が高くなるという利点
を有する。On the other hand, from the viewpoint of durability, the lower the concentration of the carrier transport substance in the carrier transport layer, the stronger the coating strength of the carrier transport layer will be, making it less likely to be scratched. It has the advantage that there is little friction on the surface due to the magnetic brush, and it has extremely high durability.
従ってキャリア輸送物質の濃度が低くても感度の低下の
少ないキャリア輸送物質の開発が望まれていた。Therefore, it has been desired to develop a carrier transporting substance that exhibits less decrease in sensitivity even when the concentration of the carrier transporting substance is low.
現在、複写機、プリンター等において、高速複写の要請
が更に高まり、複写枚数も増大してより高い耐久性が要
求されている。しかし、現状では、電子写真感光体の疲
労の低減と高感度、高速応答性との両立は困難である。Currently, there is an increasing demand for high-speed copying in copying machines, printers, etc., and the number of copies is also increasing, requiring higher durability. However, at present, it is difficult to achieve both reduction in fatigue and high sensitivity and high-speed response of electrophotographic photoreceptors.
ハ0発明の目的
本発明の目的は、操り返し使用時における帯電能の安定
化、残留電位の低減を実現でき、かつ、高感度であって
高速応答性を付与しうる感光体を提供することである。An object of the present invention is to provide a photoreceptor that can stabilize charging ability and reduce residual potential during repeated use, and that can provide high sensitivity and high-speed response. It is.
二0発明の構成及びその作用効果
本発明は、下記一般式(1)で表される化合物と下記一
般式(n)で表される化合物とからなる群より選ばれた
化合物と、電子受容性物質とを有する感光体に係るもの
である。20 Structure of the invention and its effects This invention provides a compound selected from the group consisting of a compound represented by the following general formula (1) and a compound represented by the following general formula (n), and an electron-accepting compound. The present invention relates to a photoreceptor having a substance.
一般式(1) (Ar’は置換若しくは未置換のアリール基を表す。General formula (1) (Ar' represents a substituted or unsubstituted aryl group.
Ar”は置換若しくは未置換のアリーレン基を表す。Ar" represents a substituted or unsubstituted arylene group.
Ar3はp−フェニレン基又はナフチレン基を表す。Ar3 represents a p-phenylene group or a naphthylene group.
RI、R2は置換若しくは未置換のアルキル基を表す、
〕
一般式(n)
Ar’、Ar5は置換若しくは未置換のフェニル基を表
す。RI and R2 represent a substituted or unsubstituted alkyl group,
] General formula (n) Ar' and Ar5 represent a substituted or unsubstituted phenyl group.
m、nばO又は1を表し、mとnとが同時にOになるこ
とはない、〕
本発明の感光体によれば、前記一般式(1)、(n)で
示される化合物のキャリア輸送能を利用し、これをキャ
リアの発生と輸送とをそれぞれ別個の物質で行ういわゆ
る機能分離型電子写真感光体のキャリア輸送物質として
用いることにより、被膜物性に優れ、低キヤリア輸送物
質濃度においても電荷保持力、感度、残留電位等の電子
写真特性に優れ、かつ繰り返し使用に供したときにも疲
労劣化が少ない上、熱、オゾンあるいは光に対しても安
定した特性を発揮し得る。m and n represent O or 1, and m and n do not become O at the same time.] According to the photoreceptor of the present invention, carrier transport of the compound represented by the general formula (1) or (n) is carried out. By using this material as a carrier transport material in a so-called function-separated electrophotographic photoreceptor in which carrier generation and transport are performed using separate substances, the coating has excellent physical properties and can maintain charge even at low carrier transport material concentrations. It has excellent electrophotographic properties such as holding power, sensitivity, and residual potential, and exhibits little fatigue deterioration even after repeated use, and exhibits stable properties against heat, ozone, and light.
特に、低キャリア輸送物!濃度でも電子写真特性に優れ
ていることから、感光層中での一般式(1)、(I[)
の化合物の濃度を低くすることにより、感光体の被膜強
度を大きくでき、耐久性を向上させることができる。こ
とに、感光体の表面側に存在する層、例えばキャリア輸
送層(後述)では、この効果が顕著である。Especially low carrier shipments! General formulas (1) and (I[) in the photosensitive layer have excellent electrophotographic properties in terms of density.
By lowering the concentration of the compound, the strength of the coating on the photoreceptor can be increased and the durability can be improved. This effect is particularly noticeable in layers existing on the surface side of the photoreceptor, such as a carrier transport layer (described later).
また、キャリア輸送物質の濃度を下げることにより、半
導体レーザー使用の反転現像を行うプリンターにおいて
は、黒点状の画像欠陥として表れる電位欠陥を効果的に
防止できる。Further, by lowering the concentration of the carrier transport substance, potential defects that appear as black dot-like image defects can be effectively prevented in printers that perform reversal development using a semiconductor laser.
また、「電子受容性物質」を感光体に含有せしめたこと
も重要である。It is also important that the photoreceptor contains an "electron-accepting substance."
即ち、かかる構成の採用により、繰り返し使用時の感光
体の疲労を低減することができ、光感度を良好に保ちう
る。また、残留電位上昇も防止でき、帯電能も良好に保
ちうる。That is, by employing such a configuration, it is possible to reduce fatigue of the photoreceptor during repeated use, and it is possible to maintain good photosensitivity. Further, an increase in residual potential can be prevented, and charging ability can also be maintained well.
特に、キャリア輸送物質の濃度を低くした場合には、繰
り返し使用時に感光体が疲労し易くなり、残留電位も上
昇し易い傾向がある。従って、電子受容性物質の添加に
より著しい効果を達成しうる。In particular, when the concentration of the carrier transport substance is lowered, the photoreceptor tends to become fatigued during repeated use and the residual potential tends to increase. Therefore, significant effects can be achieved by adding electron-accepting substances.
特に、負帯電使用の感光体におけるキャリア輸送層(後
述)では、電子受容性物質の添加による効果が顕著であ
る。Particularly, in the carrier transport layer (described later) of a negatively charged photoreceptor, the effect of adding an electron-accepting substance is remarkable.
次に、一般式(I)、(If)で表される化合物につい
て述べる。Next, compounds represented by general formulas (I) and (If) will be described.
式中、Ar’はアリール基を表し、好ましくはフェニル
基、ナフチル基を表す6Ar”はアリーレン又はナフチ
レン基を表す。ナフチレン基のZta位置には特に制限
はない。In the formula, Ar' represents an aryl group, preferably a phenyl group, or a naphthyl group, and 6Ar'' represents an arylene or naphthylene group. There is no particular restriction on the Zta position of the naphthylene group.
R’、R”はアルキル基を表し、好ましくは炭素原子数
1個から8個までのアルキル基を表す。R' and R'' represent an alkyl group, preferably an alkyl group having 1 to 8 carbon atoms.
これらについて、好ましい置換基としては、アルキル基
、アラルキル基、アルコキシ基、ハロゲン原子、アリー
ル基、アリールオキシ基、シアノ基、若しくは置換アミ
ノ基等が挙げられる。置換アルキル基にはアラルキル基
を含み、アラルキル基としてはベンジル基、フェネチル
基が好ましい。Preferred substituents for these include an alkyl group, an aralkyl group, an alkoxy group, a halogen atom, an aryl group, an aryloxy group, a cyano group, or a substituted amino group. The substituted alkyl group includes an aralkyl group, and the aralkyl group is preferably a benzyl group or a phenethyl group.
一般式(II)において、R3、R4はジアルキルアミ
ノ基を表し、好ましくはジメチルアミノ基、ジエチルア
ミノ基、ジプロピルアミノ基、ジブチルアミノ基を例示
できる。ジアルキルアミノ基の置換位置はパラ位が好ま
しい、Ar’、Ar’はフェニル基を表し、このフェニ
ル基の置換基としては上述のものを例示できるが、特に
メチル基、メトキシ基、ハロゲン原子等が好ましく、置
換位置はパラ位が好ましい。In general formula (II), R3 and R4 represent a dialkylamino group, and preferred examples include a dimethylamino group, a diethylamino group, a dipropylamino group, and a dibutylamino group. The substitution position of the dialkylamino group is preferably the para position. Ar' and Ar' represent a phenyl group, and examples of substituents for this phenyl group include those mentioned above, but in particular, a methyl group, a methoxy group, a halogen atom, etc. Preferably, the substitution position is preferably the para position.
キャリア輸送物質として、一般式〔1〕で表される化合
物の中から単独であるいは二種以上の組合せとして用い
る゛ことができる。一般式(n)で表される化合物につ
いても同様である。また、−般式(1)、(II)で表
される化合物を互いに併用することもできる。As the carrier transport substance, compounds represented by the general formula [1] can be used alone or in combination of two or more. The same applies to the compound represented by the general formula (n). Moreover, the compounds represented by formulas (1) and (II) can also be used together.
次に、一般式(1)、(II)で表される化合物の具体
例を例示するが、これらにより限定されるものではない
。Next, specific examples of compounds represented by general formulas (1) and (II) will be illustrated, but the invention is not limited thereto.
例示化合物
(以下余白)
■
B
■
■−18
■
■
■−16
■−に
■−21
■
■
η
以上の様なスチルベン誘導体は、公知の合成方法により
容易に合成することができる。Exemplary compounds (blank below) ■ B ■ ■-18 ■ ■ ■-16 ■-2-21 ■ ■ η The above-mentioned stilbene derivatives can be easily synthesized by known synthesis methods.
(以下余白)
■
■
■
■−招
■
■
δ
■
l−10
■
■−12
■−17
■
■
■
■−加
■−21
1[−25
■−乙
l−26
■−乙
l−27
■−冴
■−田
■−四
l−30
本発明で使用する電子受容性物質とは、電子親和力の大
きい化合物を指すが、例えば次のような化合物を例示で
きる。(Leaving space below) ■ ■ ■ ■−Invitation ■ ■ δ ■ l−10 ■ ■−12 ■−17 ■ ■ ■ ■−加■−21 1 [−25 ■−Otsu l−26 ■−Otsu l−27 ■ -Sae■-Da-41-30 The electron-accepting substance used in the present invention refers to a compound having a large electron affinity, and examples thereof include the following compounds.
即ち、無水コハク酸、無水マレイン酸、ジブロム無水コ
ハク酸、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、テトラシアノエチレン、テトラシアノキノジメ
タン、0−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、パラニトロベンゾニ
トリル、ピクリルクロライド、キノンクロルイミド、ク
ロラニル、ブルマニル、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、9−
フルオレニリデンー〔ジシアノメチレンマロノジニトリ
ル〕、ポリニトロ−9−フルオレニリデンー〔ジシアノ
メチレンマロノジニトリル〕、ピクリン酸、0−ニトロ
安息香酸、pニトロ安息香酸、3,5.−ジニトロ安息
香酸、ペンタフルオロ安息香酸、5−ニトロサリチル酸
、3.5−ジニトロサルチル酸、フタル酸、メリット酸
、その他の電子親和力の大きい化合物の一種又は二種以
上を挙げることができる。これらのうち、フルオレノン
系、キノン系や、C1,CN、No、等の電子吸引性の
置換基のあるベンゼン誘導体が特によい。Namely, succinic anhydride, maleic anhydride, dibromo succinic anhydride, phthalic anhydride, tetrachlorophthalic anhydride, tetrabromo phthalic anhydride, 3-nitro phthalic anhydride, 4
-Nitrophthalic anhydride, pyromellitic anhydride, mellitic anhydride, tetracyanoethylene, tetracyanoquinodimethane, 0-dinitrobenzene, m-dinitrobenzene,
1.3゜5-trinitrobenzene, paranitrobenzonitrile, picryl chloride, quinone chlorimide, chloranil, brumanil, dichlorodicyanobarabenzoquinone, anthraquinone, dinitroanthraquinone, 9-
Fluorenylidene [dicyanomethylene malonodinitrile], polynitro-9-fluorenylidene [dicyanomethylene malonodinitrile], picric acid, 0-nitrobenzoic acid, p-nitrobenzoic acid, 3,5. -Dinitrobenzoic acid, pentafluorobenzoic acid, 5-nitrosalicylic acid, 3.5-dinitrosalicylic acid, phthalic acid, mellitic acid, and one or more kinds of other compounds with high electron affinity can be mentioned. Among these, fluorenone series, quinone series, and benzene derivatives having electron-withdrawing substituents such as C1, CN, and No are particularly preferred.
電子受容性物質としては、電子親和力が0.3〜1.8
eVのものが好ましく 、0.5〜l−5eVのものが
更に好ましい。As an electron-accepting substance, electron affinity is 0.3 to 1.8.
eV is preferable, and 0.5 to 1-5 eV is more preferable.
本発明の感光体の感光層において、電子受容性物質とキ
ャリア輸送物質との含有量比は、重量比で電子受容性物
質:キャリア輸送物質=0.05〜50:100が好ま
しく 、0.1〜10 : 100が更に好ましい、こ
れにより、更に残留電位上昇を抑制しつつかつ帯電能も
高くする効果がある。In the photosensitive layer of the photoreceptor of the present invention, the content ratio of the electron-accepting substance to the carrier-transporting substance is preferably 0.05 to 50:100 by weight, and 0.1. ˜10:100 is more preferable, which has the effect of further suppressing the increase in residual potential and increasing the charging ability.
次に、感光体の構成、処方等について述べる。Next, the structure, prescription, etc. of the photoreceptor will be described.
本発明の感光体は、第1図および第2図に示すように導
電性支持体1上にキャリア発生物質を主成分とするキャ
リア発生層2と本発明の化合物をキャリア輸送物質の主
成分として含有するキャリア輸送層3との積層体より成
る感光層4を設ける。As shown in FIGS. 1 and 2, the photoreceptor of the present invention comprises a carrier generating layer 2 containing a carrier-generating substance as a main component on a conductive support 1, and a carrier-generating layer 2 containing a carrier-generating substance as a main component and the compound of the present invention as a main component of a carrier-transporting substance. A photosensitive layer 4 made of a laminate with a carrier transport layer 3 containing the photosensitive layer 4 is provided.
第3図および第4図に示すようにこの感光層4は、導電
性支持体1上に設けた中間層5を介して設けてもよい、
このように感光層4を二層構成としたときに最もすぐれ
た電子写真特性を有する電子写真感光体が得られる。ま
た本発明においては、第5図および第6図に示すように
前記キャリア輸送物質を主成分とする層6中に微粒子状
のキャリア発生物質7を分散してなる感光層4を導電性
支持体1上に直接ある・いは、中間層5を介して設けて
もよい。As shown in FIGS. 3 and 4, this photosensitive layer 4 may be provided through an intermediate layer 5 provided on the conductive support 1.
When the photosensitive layer 4 has a two-layer structure in this manner, an electrophotographic photoreceptor having the best electrophotographic properties can be obtained. Further, in the present invention, as shown in FIGS. 5 and 6, a photosensitive layer 4 formed by dispersing a carrier generating substance 7 in the form of fine particles in a layer 6 mainly composed of the carrier transporting substance is used as a conductive support. 1 or may be provided via an intermediate layer 5.
更に前記感光層4の上には必要に応じ保護層8を設けて
もよい。Furthermore, a protective layer 8 may be provided on the photosensitive layer 4 if necessary.
ここで感光層4を二層構成としたときにキャリア発生層
2とキャリア輸送層3のいずれを上層とするかは、帯電
極性を正、負のいずれに選ぶかによって決定される。す
なわち負帯電型感光層とする場合は、キャリア輸送層3
を上層とするのが有利であり、これは当該キャリア輸送
層3中のキャリア輸送物質が、正孔に対して高い輸送能
を有する物質であるからである。When the photosensitive layer 4 has a two-layer structure, which of the carrier generation layer 2 and the carrier transport layer 3 is to be the upper layer is determined by whether the charging polarity is positive or negative. That is, in the case of a negatively charged photosensitive layer, the carrier transport layer 3
It is advantageous to use the carrier transport layer 3 as the upper layer because the carrier transport material in the carrier transport layer 3 is a material that has a high transport ability for holes.
キャリア輸送層3においては、本発明のキャリア輸送物
質の含有比を、本発明のキャリア輸送物質1重量部に対
して結着剤0.8〜10重量部とするのが好ましい。ま
た、本発明のキャリア輸送物質をキャリア発生層2に入
れることもでき、このときの含有量比は、本発明のキャ
リア輸送物質:キャリア発生物質=(20〜80重量部
: 100重量部)とするのが好ましい。In the carrier transport layer 3, the content ratio of the carrier transport substance of the present invention is preferably 0.8 to 10 parts by weight of the binder to 1 part by weight of the carrier transport substance of the present invention. Further, the carrier transporting substance of the present invention can be added to the carrier generation layer 2, and the content ratio at this time is as follows: carrier transporting substance of the present invention: carrier generating substance = (20 to 80 parts by weight: 100 parts by weight). It is preferable to do so.
電子受容性物質は、キャリア発生層2、キャリア輸送層
3、下引N5、単層構成感光層、保護層のいずれに加え
てもよく、複数層に加えてもよい。The electron-accepting substance may be added to any of the carrier generation layer 2, the carrier transport layer 3, the sublayer N5, the single-layer photosensitive layer, and the protective layer, or may be added to multiple layers.
電子受容性物質の添加量は、感光体の層構成、キャリア
輸送物’I (CTM)の種類等によって一定ではない
が、一応下記の範囲が好ましい。The amount of the electron-accepting substance added is not constant depending on the layer structure of the photoreceptor, the type of carrier transport material 'I (CTM), etc., but it is preferably within the following range.
キャリア発生層に入れる場合は、キャリア発生物質(C
GM)100重量部に対して0.01〜50重量部が好
ましく、0.1〜20重量部とするのがより好ましい。When entering the carrier generation layer, a carrier generation substance (C
It is preferably 0.01 to 50 parts by weight, more preferably 0.1 to 20 parts by weight, per 100 parts by weight of GM).
キャリア輸送層に入れる場合はCTM100重量部に対
し0.01〜50重量部が好ましく 、0.01〜10
重量部とするのがより好ましい、下引層等の中間層、又
は保護層に入れる場合は、核層を構成するバインダー物
質(樹脂)100重量部に対し0.01〜50重量部と
するのが好ましい。When added to the carrier transport layer, it is preferably 0.01 to 50 parts by weight per 100 parts by weight of CTM, and 0.01 to 10 parts by weight.
When included in an intermediate layer such as an undercoat layer, or a protective layer, it is preferably contained in parts by weight of 0.01 to 50 parts by weight based on 100 parts by weight of the binder material (resin) constituting the core layer. is preferred.
本発明の感光体に使用するキャリア発生物質としては、
一般に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、無機顔料及び有機色素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
うな有機顔料を用いてもよい。The carrier generating substance used in the photoreceptor of the present invention is as follows:
In general, 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, and lead sulfide, the following Organic pigments such as those shown in the representative examples may also be 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、ピラントロン誘導体、
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
(10)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
更に、以下のキャリア発生物質を好ましいものとして具
体的に例示できる。(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 , ananthanthrone derivatives, dibenzpyrenequinone derivatives, pyranthrone 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 phthalocyanines and metal-free phthalocyanines (6) Diphenylmethane pigments pigments, carbonium pigments such as triphenylmethane pigments, xanthine pigments and acridine pigments (7) quinone imine pigments such as azine pigments, oxazine pigments and thiazine pigments (8) methine pigments such as cyanine pigments and azomethine pigments (9) quinoline Pigments (10) Nitro pigments (11) Nitroso pigments (12) Benzoquinone and naphthoquinone pigments (13)
Naphthalimide pigments (14) Perinone pigments such as bisbenzimidazole derivatives In addition, the following carrier-generating substances can be specifically exemplified as preferred.
アゾ系例示顔料
VT−(A)
(以下余白)
本発明に用いられるCGM化合物としては、上記例示化
合物の他に、特開昭60−172045号等に記載され
た化合物を用いることができる。Azo Exemplary Pigment VT-(A) (Hereinafter, blank) As the CGM compound used in the present invention, in addition to the above-mentioned exemplary compounds, compounds described in JP-A-60-172045 and the like can be used.
本発明において用いられるキャリア輸送物質は、それ自
体では被膜形成能がないため種々の結着剤と組合せて感
光層が形成される。The carrier transporting substance used in the present invention does not have the ability to form a film by itself, so a photosensitive layer is formed by combining it with various binders.
キャリア発生層およびキャリア輸送層に用いられる結着
剤としては、任意のものを用いることができるが、疎水
性の電気絶縁性フィルム形成性高分子重合体を用いるこ
とが好ましい。このような高分子重合体としては、例え
ば次のものを挙げることができるが、これらに限定され
るものではない。Although any binder can be used for the carrier generation layer and the carrier transport layer, it is preferable to use a hydrophobic electrically insulating film-forming polymer. Examples of such high molecular weight polymers include, but are not limited to, the following.
(1)ポリカーボネート
(2)ポリエステル
(3)メタクリル樹脂
(4)アクリル樹脂
(5)ポリ塩化ビニル
(6)ポリ塩化ビニリデン
(7)ボリスチレン
(8)、I’ぐリビニルアセテート
(9)スチレン共重合樹脂(例えば、スチレンブタジェ
ン共重合体、スチレン−メタクリル酸メチル共重合体、
等)
(10)アクリロニトリル系共重合体樹脂(例えば、塩
化ビニリデン−アクリロニトリル共重合体、等)
(11)塩化ビニル−酢酸ビニル共重合体(12)塩化
ビニル−酢酸ビニル−無水マレイン酸共重合体
(13)シリコーン樹脂
(14)シリコーン−アルキッド樹脂
(15)フェノール樹脂(例えば、フェノール−ホルム
アルデヒド樹脂、クレゾールホルムアルデヒド樹脂、等
)
(16)スチレン−アルキッド樹脂
(17)ポリ−N−ビニルカルバゾール(18)ポリビ
ニルブチラール
(19)ポリビニルホルマール
(20)ポリヒドロキシスチレン
これらの結着剤は、単独であるいは2種以上の混合物と
して用いることができる。(1) Polycarbonate (2) Polyester (3) Methacrylic resin (4) Acrylic resin (5) Polyvinyl chloride (6) Polyvinylidene chloride (7) Boristyrene (8) I'glyvinyl acetate (9) Styrene copolymerization Resins (e.g., styrene-butadiene copolymer, styrene-methyl methacrylate copolymer,
(10) Acrylonitrile copolymer resin (e.g. vinylidene chloride-acrylonitrile copolymer, etc.) (11) Vinyl chloride-vinyl acetate copolymer (12) Vinyl chloride-vinyl acetate-maleic anhydride copolymer (13) Silicone resin (14) Silicone-alkyd resin (15) Phenolic resin (e.g., phenol-formaldehyde resin, cresol formaldehyde resin, etc.) (16) Styrene-alkyd resin (17) Poly-N-vinylcarbazole (18) Polyvinyl butyral (19) Polyvinyl formal (20) Polyhydroxystyrene These binders can be used alone or in a mixture of two or more.
また前記中間層は接着層またはバリヤ層として機能する
もので、前記結着剤樹脂のほかに、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、カゼインなどが用いられる。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, casein, etc. are used.
本発明の感光体の構成に用いられる導電性支持体として
は、主として下記のものが用いられるが、これらにより
限定されるものではない。As the conductive support used in the construction of the photoreceptor of the present invention, the following are mainly used, but the present invention is not limited thereto.
(1)アルミニウム板、ステンレス板などの金属板、お
よびドラム形状のもの。(1) Metal plates such as aluminum plates and stainless steel plates, and drum-shaped ones.
(2)祇あるいはプラスチックフィルムなどの支持体上
にアルミニウム、パラジウム、金などの金属薄層をラミ
ネートもしくは蒸着によって設けたもの。(2) A thin layer of metal such as aluminum, palladium, or gold is provided on a support such as aluminum or plastic film by lamination or vapor deposition.
(3)紙、あるいはプラスチックフィルムなどの支持体
上に導電性ポリマー、酸化インジウム、酸化錫などの導
電性化合物の層を塗布もしくは蒸着によって設けたもの
。(3) A layer of a conductive compound such as a conductive polymer, indium oxide, or tin oxide is provided on a support such as paper or a plastic film by coating or vapor deposition.
本発明の感光体では、本発明の効果を損なわない範囲で
他のキャリア輸送物質を併用することも可能である。In the photoreceptor of the present invention, it is also possible to use other carrier transport substances in combination within a range that does not impair the effects of the present invention.
また、キャリア発生層とキャリア輸送層とで互いに相異
なるキャリア輸送物質を使用することも可能である。It is also possible to use different carrier transport materials in the carrier generation layer and the carrier transport layer.
二層構成の感光層を構成するキャリア発生層は、導電性
支持体、もくしはキャリア輸送層上に直接あるいは必要
に応じて接着層もしくはバリヤ層などの中間層を設けた
上に、次の方法によって形成することができる。The carrier generation layer constituting the two-layered photosensitive layer is formed directly on the conductive support or carrier transport layer, or with an intermediate layer such as an adhesive layer or barrier layer as required, and then It can be formed by a method.
(1)真空蒸着法
(2)キャリア発生物質を適当な溶剤に溶解した溶液を
塗布する方法
(3)キャリア発生物質をボールミル、サンドグライン
ダ等によって分散媒中で微細粒子状とし必要に応じて、
結着剤と混合分散して得られる分散液を塗布する方法。(1) Vacuum deposition method (2) Method of applying a solution of a carrier-generating substance dissolved in a suitable solvent (3) Forming the carrier-generating substance into fine particles in a dispersion medium using a ball mill, sand grinder, etc.
A method of applying a dispersion obtained by mixing and dispersing a binder.
本発明に係わるキャリア輸送層およびキャリア発生層等
の構成層の形成には、真空蒸着、スパフタリング、CV
D等の気相堆積法あるいはディッピング、スプレィ、ブ
レード、ロール法等の塗布方法が任意に用いられる。Formation of constituent layers such as a carrier transport layer and a carrier generation layer according to the present invention includes vacuum evaporation, sputtering, CV
A vapor deposition method such as D or a coating method such as dipping, spraying, blade, or roll method may be arbitrarily used.
キャリア発生層の厚さは、0.01μm〜5μmである
ことが好ましく、更に好ましくは0.05〜3μmであ
る。The thickness of the carrier generation layer is preferably 0.01 μm to 5 μm, more preferably 0.05 μm to 3 μm.
またキャリア輸送層の厚さは、必要に応じて変更し得る
が通常5〜30μmであることが好ましい。Further, the thickness of the carrier transport layer may be changed as necessary, but it is usually preferably 5 to 30 μm.
微粒子状のキャリア発生物質を分散せしめた単層構成の
感光層を形成する場合は、キャリア発生物質1重量部に
対して結着剤を5重量部以下の範囲で用いることが好ま
しい。When forming a photosensitive layer having a single layer structure in which a particulate carrier-generating substance is dispersed, it is preferable to use a binder in an amount of 5 parts by weight or less per 1 part by weight of the carrier-generating substance.
またキャリア発生層を結着剤による分散型のものとして
構成する場合には、キャリア発生物質1重量部に対して
結着剤を5重量部以下の範囲で用いることが好ましい。Further, when the carrier generation layer is configured as a dispersed type layer using a binder, it is preferable to use the binder in an amount of 5 parts by weight or less per 1 part by weight of the carrier generating substance.
なお、本発明の感光体は、ハロゲンランプ、タングステ
ンランプ、LED (発光ダイオード)、ヘリウム−ネ
オン、アルゴン、ヘリウム−カドミウム等の気体レーザ
ー、半導体レーザー等の各種光源に対し通用できる。The photoreceptor of the present invention can be used with various light sources such as halogen lamps, tungsten lamps, LEDs (light emitting diodes), gas lasers such as helium-neon, argon, and helium-cadmium, and semiconductor lasers.
本発明の感光体は、電子写真複写機、プリンター等の多
種多様の用途を有するものである。The photoreceptor of the present invention has a wide variety of uses such as electrophotographic copying machines and printers.
ホ、実施例
以下、本発明の実施例について更に詳細に説明するが、
これにより本発明は限定されるものではなく、種々の変
形した他の実施例も勿論含むものである。E. Examples Examples of the present invention will be explained in more detail below.
The present invention is not limited thereby, and of course includes other embodiments with various modifications.
(を子写真感光体の作製)
まず、以下のようにして、各電子写真感光体を作成した
。(Preparation of child photographic photoreceptors) First, each electrophotographic photoreceptor was prepared as follows.
施 1、 軒側1
ポリエステルフィルム上にアルミニウム箔をラミネート
して成る導電性支持体上にキャリア発生物質としてビス
アゾ顔料、前記CGMVI−70を1重量部とポリメチ
ルメタクリレート樹脂「ダイヤナールBR−80J
(三菱レイヨン社製)0.5重量部とを1.2−ジクロ
ルエタン100重量部に加えサンドグラインダにて4時
間分散した液を、乾燥後の膜厚が0.4μmになるよう
に塗布し、キャリア発生層を形成した。Application 1. Eave side 1 On a conductive support made of aluminum foil laminated on a polyester film, 1 part by weight of bisazo pigment, the above-mentioned CGMVI-70, as a carrier generating substance and polymethyl methacrylate resin "Dianal BR-80J" were applied.
(Mitsubishi Rayon Co., Ltd.) 0.5 parts by weight was added to 100 parts by weight of 1,2-dichloroethane and dispersed for 4 hours using a sand grinder, and a solution was applied so that the film thickness after drying was 0.4 μm. A carrier generation layer was formed.
次いで、キャリア輸送物質として例示化合物■2を4.
0重量部、1,3.5−トリニトロベンゼン、ポリカー
ボネート樹脂「パンライトに一1500J(奇人化成社
製)10重量部を1.2−ジクロルエタン100重量部
に溶解した液を、乾燥後の膜厚が15μmになるように
塗布し、キャリア輸送層を形成し、実施例の電子写真感
光体を得た。1.3゜5−トリニトロベンゼンの添加量
は、キャリア輸送物質(CTM)に対し0.1重量%と
じた。Next, exemplified compound (2) was added to 4. as a carrier transport substance.
0 parts by weight, 1,3.5-trinitrobenzene, polycarbonate resin 10 parts by weight of Panlite 11500J (manufactured by Kijin Kasei Co., Ltd.) was dissolved in 100 parts by weight of 1,2-dichloroethane, and the film thickness after drying was A carrier transport layer was formed and an electrophotographic photoreceptor of the example was obtained.The amount of 1.3° 5-trinitrobenzene added was 0.3° with respect to the carrier transport material (CTM). It was bound at 1% by weight.
また、実施例1において、CTMを下記(ii )に変
え、また電子受容性物質を取り除いた。他は、実施例1
と同様にして比較例の電子写真感光体を作製した。Furthermore, in Example 1, CTM was changed to (ii) below, and the electron-accepting substance was removed. Others are Example 1
An electrophotographic photoreceptor of a comparative example was produced in the same manner as described above.
例5.6、 較 5.6
実施例1において、CGM、CTM、電子受容性物質(
添加化合物)をそれぞれ下記表に示すように変え、他は
実施例1と同様にして各電子写真感光体を作製した。Example 5.6, Comparison 5.6 In Example 1, CGM, CTM, electron-accepting substance (
Each electrophotographic photoreceptor was produced in the same manner as in Example 1 except that the additive compounds) were changed as shown in the table below.
2、 r2
ポリエステルフィルム上にアルミニウムを蒸着して成る
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tl rエスレフクMF10」(積木化学社製
)より成る厚さ0.1μmの中間層を設けた。2. r2 A 0.1 μm thick medium made of vinyl chloride-vinyl acetate-maleic anhydride co-tl r S-refuku MF10 (manufactured by Block Chemical Co., Ltd.) was placed on a conductive support made by vapor-depositing aluminum on a polyester film. Layers were set up.
その上に、ジブロムアンスアンスロン[モノライトレッ
ド2YJ (IC1社製)(前記CGMVI73)1
重量部とポリカーボネート樹脂[パンライ)L−125
0J (奇人化成社製)0.5重量部とを1.2−ジ
クロルエタン100重量部に混合し、ボールミルで24
時間分散した液を乾燥後の膜厚が1μmになるように塗
布してキャリア発生層を形成した。On top of that, 1
Weight parts and polycarbonate resin [Panrai] L-125
0J (manufactured by Kijin Kasei Co., Ltd.) and 0.5 parts by weight were mixed with 100 parts by weight of 1,2-dichloroethane.
A carrier generation layer was formed by applying the time-dispersed liquid so that the film thickness after drying was 1 μm.
0.1重量%とじた。It was bound at 0.1% by weight.
また、実施例2において、CTMを下記(iii )に
変え、これ以外は実施例1と同様にして比較例2の電子
写真感光体を作成した。Further, in Example 2, CTM was changed to (iii) below, and an electrophotographic photoreceptor of Comparative Example 2 was prepared in the same manner as in Example 1 except for this.
CTM
(ii )
(iii )
一ト樹脂「パンライトL −L250J 10重量部を
1゜2−ジクロルエタン80重量部に溶解した液を、乾
燥後の膜厚が16μmになるように塗布してキャリア輸
送層を形成し、実施例2の電子写真感光体を作成した。CTM (ii) (iii) A solution prepared by dissolving 10 parts by weight of Panlite L-L250J in 80 parts by weight of 1°2-dichloroethane was applied so that the film thickness after drying was 16 μm, and the carrier was transported. A layer was formed to produce an electrophotographic photoreceptor of Example 2.
プロマニルの添加量は、CTMに対し公知の方法で得ら
れたCGMVI−66(ε型銅)タロシアニン) 1.
0 gをポリビニルブチラール(エスレフクBL−3:
積水化学工業社製)2.0g、1,2−ジクロルエタン
98m1からなる混合液中に添加し、超音波分散機によ
り分散して分散液を得た。この分散液を、乾燥後の膜厚
が0.3μmとなるように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よりなる導電性支持体に塗布
、乾燥してCGLを形成した0次いで、キャリア輸送物
質としてn−4を10重量部、添加化合物m−ジニトロ
ベンゼン及び下記構造式で示されるポリカーボネート樹
脂Z−200(三菱ガス化学社製)20重量部を1.2
−ジクロルエタン100重量部に対して溶解した液を1
5μmになるように塗布して、実施例3の感光体を作成
した。但し、m−ジニトロベンゼンの添加量は、CTM
に対し0.1重量%とした。The amount of promanil added was as follows: CGMVI-66 (ε-type copper) talocyanin) obtained by a known method for CTM.
0 g of polyvinyl butyral (Srefuku BL-3:
(manufactured by Sekisui Chemical Co., Ltd.) and 98 ml of 1,2-dichloroethane, and dispersed with an ultrasonic disperser to obtain a dispersion. This dispersion was applied to a conductive support made of a polyester film laminated with aluminum foil so that the film thickness after drying was 0.3 μm, and dried to form a CGL. 4, 1.2 parts by weight of the additive compound m-dinitrobenzene, and 20 parts by weight of polycarbonate resin Z-200 (manufactured by Mitsubishi Gas Chemical Co., Ltd.) represented by the following structural formula.
- 1 part of the solution dissolved in 100 parts by weight of dichloroethane
A photoreceptor of Example 3 was prepared by coating the film to a thickness of 5 μm. However, the amount of m-dinitrobenzene added is CTM
0.1% by weight.
また、実施例3において、CTMを上記(ij )に変
え、これ以外は実施例3と同様にして比較例3の電子写
真感光体を得た。Further, in Example 3, the CTM was changed to the above (ij), and the electrophotographic photoreceptor of Comparative Example 3 was obtained in the same manner as in Example 3 except for this.
更に、実施例3において、CGM、CTM、電子受容性
物質(添加化合物)を下記表に示すように変え、これ以
外は実施例3と同様にして実施例4、比較例4の電子写
真感光体を得た。Furthermore, in Example 3, the CGM, CTM, and electron-accepting substance (additive compound) were changed as shown in the table below, and the electrophotographic photoreceptors of Example 4 and Comparative Example 4 were manufactured in the same manner as in Example 3 except for the above. I got it.
(感光体特性の測定)
以上のようにして得た各電子写真感光体について、静電
複写紙試験装置rEPA−8100」(川口電機製作所
)を用いてグイナミソク方式で電子写真特性を測定した
。(Measurement of Photoreceptor Characteristics) The electrophotographic characteristics of each of the electrophotographic photoreceptors obtained as described above were measured by the Guinamisoku method using an electrostatic copying paper tester rEPA-8100 (Kawaguchi Denki Seisakusho).
即ち、タングステンランプの光を感光体表面の照度が3
.51!uxになるようにして照射し、表面電位を一6
00■から一1O0Vに減衰させるのに要する露光量(
感度) Ein:、並びに301 ux−secの露光
量で照射した後の表面電位(残留電位)■えをそれぞれ
求めた。In other words, the illuminance of the light from the tungsten lamp on the surface of the photoreceptor is 3.
.. 51! ux, and the surface potential is -6.
The amount of exposure required to attenuate from 00■ to -1O0V (
Sensitivity) Ein: and surface potential (residual potential) after irradiation with an exposure amount of 301 ux-sec were determined.
また、帯電−露光−転写の電子写真プロセスを1万回繰
り返して行い、1万回コピー後のEl:;を求め、かつ
■えの変動値ΔVえを測定した。結果は下記表に示すと
うりである。In addition, the electrophotographic process of charging-exposure-transfer was repeated 10,000 times, El:; after 10,000 copies was determined, and the variation value ΔV during printing was measured. The results are shown in the table below.
表
表に示すように、実施例の電子写真感光体は、比較例の
感光体に比べて、感度、繰り返し使用時の安定性におい
て優れている。As shown in the table, the electrophotographic photoreceptors of Examples are superior to the photoreceptors of Comparative Examples in sensitivity and stability during repeated use.
くキャリア輸送物質の含有量を変更させた例について〉
前記した実施例3と同様にして、キャリア発生層を形成
した。Regarding an example in which the content of the carrier transport substance was changed> A carrier generation layer was formed in the same manner as in Example 3 described above.
次いで、ポリカーボネート樹脂rZ−2004(三菱ガ
ス化学社製)10重量部に対し、例示化合物(1−3、
■−3)をそれぞれキャリア輸送物質として加え、かつ
電子受容性物質(1,3,5−トリニトロベンゼン>
0.01重量部を加えて、1゜2−ジクロルエタン50
重量部に溶解し、これを塗布して膜厚20μmのキャリ
ア輸送層を有する電子写真感光体を作成した。但し、各
キャリア輸送物質の含有量は7.5重量部、6.0重量
部、5.0重量部、4.0重量部、3.0重量部に変化
させた。Next, exemplified compounds (1-3,
■-3) is added as a carrier transporting substance, and an electron accepting substance (1,3,5-trinitrobenzene>
Add 0.01 part by weight to 50% of 1°2-dichloroethane.
This was dissolved in parts by weight and coated to prepare an electrophotographic photoreceptor having a carrier transport layer with a thickness of 20 μm. However, the content of each carrier transport substance was changed to 7.5 parts by weight, 6.0 parts by weight, 5.0 parts by weight, 4.0 parts by weight, and 3.0 parts by weight.
また、キャリア輸送物質として下記構造式で表されるス
チルベン誘導体を用いた他は、上記実施例と同様にして
比較用感光体を作成した。但し、キャリア輸送物質の含
有量は上記と同様に変化させた。Further, a comparative photoreceptor was prepared in the same manner as in the above example except that a stilbene derivative represented by the following structural formula was used as a carrier transporting substance. However, the content of the carrier transport substance was changed in the same manner as above.
これらの各感光体について前述したと同様にして1万回
コピー後の感度(E::’、)を測定した。For each of these photoreceptors, the sensitivity (E::',) after 10,000 copies was measured in the same manner as described above.
結果は第7図、第8図に示すとうりである。The results are shown in FIGS. 7 and 8.
第7図、第8図に示す結果から明らかなように、実施例
の電子写真感光体は、比較用感光体に比べて感度および
繰り返しの安定性において著しく優れ、特にキャリア輸
送物質の低濃度領域においても感度の低下が少なく極め
て優れた特性を有している。As is clear from the results shown in FIGS. 7 and 8, the electrophotographic photoreceptor of the example was significantly superior in sensitivity and repetition stability compared to the comparative photoreceptor, especially in the low concentration region of the carrier transport substance. It also has extremely excellent characteristics with little decrease in sensitivity.
第1図、第2図、第3図、第4図、第5図、第6図はそ
れぞれ本発明の感光体の機械的構成例について示す断面
図である。
第7図、第8図はそれぞれキャリア輸送物質量と感度と
の関係を示すグラフである。
なお、図面に示す符号において、
1・−−一−−−−−−−−導電性支持体2−・−−−
−−−・−キャリア発生層3−・−・−キャリア輸送層
4・−−−−一・・−感光層
5−・−−−−−一一一−−中間層
6−−−一・・−キャリア輸送物質を含有する層7・−
−一一−−−−−−−キャリア発生物質8− ・−・−
保護層
である。
代理人 弁理士 逢 坂 末
弟1図
第2図
第3図
第4図
第5図
第6図
喪
■
区
1乃回コピ
伎のE寞
(luxSec)
り
区FIG. 1, FIG. 2, FIG. 3, FIG. 4, FIG. 5, and FIG. 6 are sectional views showing examples of the mechanical configuration of the photoreceptor of the present invention, respectively. FIG. 7 and FIG. 8 are graphs showing the relationship between the amount of carrier transport substance and sensitivity, respectively. In addition, in the symbols shown in the drawings, 1.
----Carrier generation layer 3--Carrier transport layer 4--Photosensitive layer 5-----11--Intermediate layer 6--1・−Layer 7 containing carrier transport substance−
−11−−−−−−Carrier generating substance 8− ・−・−
It is a protective layer. Agent Patent Attorney Aisaka Youngest brother 1 Figure 2 Figure 3 Figure 4 Figure 5 Figure 6 Mourning
Claims (1)
〔II〕で表される化合物とからなる群より選ばれた化合
物と、電子受容性物質とを有する感光体。 一般式〔 I 〕 ▲数式、化学式、表等があります▼ 〔Ar^1は置換若しくは未置換のアリール基を表す。 Ar^2は置換若しくは未置換のアリーレン基を表す。 Ar^3はp−フェニレン基又はナフチレン基を表す。 R^1、R^2は置換若しくは未置換のアルキル基を表
す。〕 一般式〔II〕 ▲数式、化学式、表等があります▼ 〔R^3、R^4はジアルキルアミノ基を表す。 Ar^4、Ar^5は置換若しくは未置換のフェニル基
を表す。 m、nは0又は1を表し、mとnとが同時に0になるこ
とはない。〕[Claims] 1. A photosensitive material comprising a compound selected from the group consisting of a compound represented by the following general formula [I] and a compound represented by the following general formula [II] and an electron-accepting substance. body. General formula [I] ▲Mathematical formulas, chemical formulas, tables, etc.▼ [Ar^1 represents a substituted or unsubstituted aryl group. Ar^2 represents a substituted or unsubstituted arylene group. Ar^3 represents a p-phenylene group or a naphthylene group. R^1 and R^2 represent substituted or unsubstituted alkyl groups. ] General formula [II] ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [R^3 and R^4 represent dialkylamino groups. Ar^4 and Ar^5 represent substituted or unsubstituted phenyl groups. m and n represent 0 or 1, and m and n are never 0 at the same time. ]
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP20432788A JPH0253066A (en) | 1988-08-17 | 1988-08-17 | Photosensitive body |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP20432788A JPH0253066A (en) | 1988-08-17 | 1988-08-17 | Photosensitive body |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH0253066A true JPH0253066A (en) | 1990-02-22 |
Family
ID=16488657
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP20432788A Pending JPH0253066A (en) | 1988-08-17 | 1988-08-17 | Photosensitive body |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH0253066A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2000330315A (en) * | 1999-03-18 | 2000-11-30 | Nec Niigata Ltd | Positively charged type electrophotographic photoreceptor and its production |
JP2004252066A (en) * | 2003-02-19 | 2004-09-09 | Minolta Co Ltd | Organic photoreceptor |
-
1988
- 1988-08-17 JP JP20432788A patent/JPH0253066A/en active Pending
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2000330315A (en) * | 1999-03-18 | 2000-11-30 | Nec Niigata Ltd | Positively charged type electrophotographic photoreceptor and its production |
JP2004252066A (en) * | 2003-02-19 | 2004-09-09 | Minolta Co Ltd | Organic photoreceptor |
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