JPH0213962A - Electrophotographic sensitive body - Google Patents
Electrophotographic sensitive bodyInfo
- Publication number
- JPH0213962A JPH0213962A JP16553788A JP16553788A JPH0213962A JP H0213962 A JPH0213962 A JP H0213962A JP 16553788 A JP16553788 A JP 16553788A JP 16553788 A JP16553788 A JP 16553788A JP H0213962 A JPH0213962 A JP H0213962A
- Authority
- JP
- Japan
- Prior art keywords
- layer
- carrier
- weight
- substituted
- unsubstituted
- 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
- 125000003118 aryl group Chemical group 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 125000000732 arylene group Chemical group 0.000 claims abstract description 3
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 3
- 125000005259 triarylamine group Chemical group 0.000 claims abstract description 3
- 108091008695 photoreceptors Proteins 0.000 claims description 67
- 239000000126 substance Substances 0.000 claims description 46
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 230000035945 sensitivity Effects 0.000 abstract description 13
- 239000000463 material Substances 0.000 abstract description 10
- 238000012546 transfer Methods 0.000 abstract description 3
- 239000000758 substrate Substances 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 84
- 150000001875 compounds Chemical class 0.000 description 19
- 230000000052 comparative effect Effects 0.000 description 17
- 239000000049 pigment Substances 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000004431 polycarbonate resin Substances 0.000 description 12
- 229920005668 polycarbonate resin Polymers 0.000 description 12
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 10
- 229910052782 aluminium Inorganic materials 0.000 description 9
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 9
- 239000011230 binding agent Substances 0.000 description 9
- 238000001035 drying Methods 0.000 description 9
- 239000004419 Panlite Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 229920006267 polyester film Polymers 0.000 description 6
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 229910052711 selenium Inorganic materials 0.000 description 5
- 239000011669 selenium Substances 0.000 description 5
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 150000001299 aldehydes Chemical class 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
- WUPHOULIZUERAE-UHFFFAOYSA-N 3-(oxolan-2-yl)propanoic acid Chemical compound OC(=O)CCC1CCCO1 WUPHOULIZUERAE-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
- 229910052980 cadmium sulfide Inorganic materials 0.000 description 3
- 230000006866 deterioration Effects 0.000 description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 3
- 238000007598 dipping method Methods 0.000 description 3
- 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 3
- 238000005259 measurement Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 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 3
- 239000011241 protective layer Substances 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-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
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-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
- 229920006026 co-polymeric resin Polymers 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 239000010419 fine particle Substances 0.000 description 2
- 239000011888 foil Substances 0.000 description 2
- 239000001023 inorganic pigment Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 239000012860 organic pigment Substances 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000002985 plastic film Substances 0.000 description 2
- 229920006255 plastic film Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- FYELSNVLZVIGTI-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-5-ethylpyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical group C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C=NN(C=1CC)CC(=O)N1CC2=C(CC1)NN=N2 FYELSNVLZVIGTI-UHFFFAOYSA-N 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
- 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
- FIHZWZBEAXASKA-UHFFFAOYSA-N Anthron Natural products COc1cc2Cc3cc(C)cc(O)c3C(=O)c2c(O)c1C=CC(C)C FIHZWZBEAXASKA-UHFFFAOYSA-N 0.000 description 1
- 229910000967 As alloy Inorganic materials 0.000 description 1
- CAQWNKXTMBFBGI-UHFFFAOYSA-N C.[Na] Chemical compound C.[Na] CAQWNKXTMBFBGI-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 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
- 239000004793 Polystyrene Substances 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 229920007962 Styrene Methyl Methacrylate Polymers 0.000 description 1
- 229910001215 Te alloy Inorganic materials 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
- 239000002253 acid Substances 0.000 description 1
- PGEHNUUBUQTUJB-UHFFFAOYSA-N anthanthrone Chemical class C1=CC=C2C(=O)C3=CC=C4C=CC=C5C(=O)C6=CC=C1C2=C6C3=C54 PGEHNUUBUQTUJB-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 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
- 150000001793 charged compounds Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 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
- 229920001940 conductive polymer Polymers 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 150000003949 imides Chemical class 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
- 230000007774 longterm Effects 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000001819 mass spectrum Methods 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
- 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
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- BUYMVQAILCEWRR-UHFFFAOYSA-N naled Chemical compound COP(=O)(OC)OC(Br)C(Cl)(Cl)Br BUYMVQAILCEWRR-UHFFFAOYSA-N 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- -1 perylene acid anhydride Chemical class 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-L phosphonate(2-) Chemical compound [O-]P([O-])=O ABLZXFCXXLZCGV-UHFFFAOYSA-L 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
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000004059 quinone derivatives Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 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
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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
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
- G03G5/0668—Dyes containing a methine or polymethine group containing only one methine or polymethine group
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は電子写真感光体に関し、より詳しくは、有機光
導電性化合物を主成分とする感光層を有する電子写真感
光体に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to an electrophotographic photoreceptor, and more particularly to an electrophotographic photoreceptor having a photosensitive layer containing an organic photoconductive compound as a main component.
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、シリコン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。たとえ
ばセレンは、結晶化すると電子写真感光体としての特性
が劣化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性能が
劣化してしまう。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。Conventionally, inorganic photoreceptors having a photosensitive layer containing an inorganic photoconductive compound such as selenium, zinc oxide, cadmium sulfide, or silicon as a main component have been widely used as electrophotographic photoreceptors. However, these were not necessarily satisfactory in terms of sensitivity, thermal stability, moisture resistance, durability, etc. For example, when selenium crystallizes, its properties as an electrophotographic photoreceptor deteriorate, making it difficult to manufacture.Also, selenium crystallizes due to heat, fingerprints, etc., and its performance as an electrophotographic photoreceptor deteriorates. In addition, cadmium sulfide and zinc oxide
There were 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なわれている。In order to overcome these drawbacks of inorganic photoreceptors, research and development have been actively conducted in recent years on organic photoreceptors having photosensitive layers containing various organic photoconductive compounds as main components.
たとえば、特公昭50−10496号にはポリ−N−ビ
ニルカルバゾール
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い。For example, Japanese Patent Publication No. 50-10496 describes an organic photoreceptor comprising a photosensitive layer containing poly-N-vinylcarbazoleolenon. However, this photoreceptor is 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 photoreceptors because each material can be selected from a wide range and a photoreceptor having arbitrary performance can be produced relatively easily.
その結果キャリア発生物質としては、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、たとえは特開昭51−94829号、同
52−72231号、同53−27033号、同55−
52063号、同58−65440号、同58−198
425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, JP-A-52-72231, JP-A-53-27033, JP-A-55-
No. 52063, No. 58-65440, No. 58-198
A wide variety of substances have been proposed, as disclosed in No. 425 and the like.
前記のごと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
すぐ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。Some electrophotographic photoreceptors using carrier transport materials such as those described above exhibit relatively excellent electrophotographic performance, but their durability against light, ozone, or electrical loads is weak, and performance may deteriorate after repeated use. Since it is stable and causes deterioration, it does not fully satisfy practical requirements, and it is desired to develop a carrier transport material that has even better carrier transport function and exhibits stable performance for long-term use. was.
更に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。Furthermore, the demand for installing organic photoreceptors in electrophotographic copying machines capable of copying at higher speeds has been increasing in recent years, and the development of photoreceptors with higher sensitivity and higher durability has been desired.
本発明は、こうした問題を解決し橿めて高感度、高耐久
性の感光体を提供すべく行なわれたものである。The present invention has been made to solve these problems and provide a highly sensitive and highly durable photoreceptor.
前記の問題は、導電性支持体上に下記一般式〔■〕で示
されるトリアリールアミン誘導体を含有する層を含んで
構成される感光層を有する電子写真感光体によって解決
される。The above problem is solved by an electrophotographic photoreceptor having a photosensitive layer comprising a layer containing a triarylamine derivative represented by the following general formula [■] on a conductive support.
一般式(1)
但し、式中Ar.、Ar2は置換,未置換のアリール基
を表し、好ましくは、置換,未置換のフェニル基、置換
,未置換のナフチル基を表す。Ar,は置換。General formula (1) However, in the formula, Ar. , Ar2 represents a substituted or unsubstituted aryl group, preferably a substituted or unsubstituted phenyl group, or a substituted or unsubstituted naphthyl group. Ar, is substitution.
未置換のアリーレン基を表し、好ましくは、置換。Represents an unsubstituted arylene group, preferably substituted.
未置換のフェニレン基、置換,未置換のナフチレン基を
表す。R,、R2、R3、RいRいR6、R7、R,は
、各々同じでも異なっていてもよく、水素原子、ハロゲ
ン原子、置換.未置換のアルキル’2f、置換,未置換
のアルコキシ基、置換,未置換のアリール基、置換,未
置換のアリールオキシ基、置換アミノ基を表し、好まし
いアリール基は、フェニル基、ナフチル基であり、好ま
しいアリールオキシ基は、フェノキシ基である。Represents an unsubstituted phenylene group, substituted or unsubstituted naphthylene group. R,, R2, R3, R, R6, R7, R, may be the same or different, and each represents a hydrogen atom, a halogen atom, a substituted... It represents unsubstituted alkyl'2f, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryl group, substituted or unsubstituted aryloxy group, or substituted amino group, and preferred aryl groups are phenyl group and naphthyl group. , a preferred aryloxy group is a phenoxy group.
Xは酸素原子、硫黄原子、)N−R,を表し、R。X represents an oxygen atom, a sulfur atom, )NR, and R.
は、水素原子、置換,未置換のアルキル基を表ず。does not represent a hydrogen atom or a substituted or unsubstituted alkyl group.
すなわち本発明においては、前記一般式[1)で示され
る化合物のキャリア輸送能を活用し、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、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電子写真感光体を作成するこ
とかできる。That is, in the present invention, the carrier transporting ability of the compound represented by the general formula [1] is utilized to create a carrier transporting material for a functionally separated electrophotographic photoreceptor in which carrier generation and transport are performed using separate substances. By using it as a coating material, the film has excellent physical properties and electrophotographic properties such as charge retention, sensitivity, and residual potential.It also shows little fatigue deterioration even after repeated use, and is resistant to heat. It is possible to create an electrophotographic photoreceptor that exhibits stable characteristics even against ozone or light.
また本発明で用いられるキャリア輸送物質は、前記一般
式〔I〕で示される化合物の中から単独あるいは2種以
上の組合せで用いることができ、また他のキャリア輸送
物質との組合せで使用してもよい。Further, the carrier transporting substance used in the present invention can be used alone or in combination of two or more of the compounds represented by the general formula [I], and can also be used in combination with other carrier transporting substances. Good too.
前記一般式〔I〕で示される本発明に有効なキリア輸送
物質の具体例としては、例えば、次の構造式を有するも
のか挙げられるが、これによって本発明に係わるキャリ
ア輸送物質か限定されるも例示化合物
ヤ
前記キャリア輸送物質は、公知の合成方法によって容易
に合成される。例えば、時開゛昭58−198425号
記載の方法が参照される。Specific examples of the carrier transport substance represented by the general formula [I] that are effective in the present invention include those having the following structural formula, but the carrier transport substance according to the present invention is limited by this. Exemplary Compounds The carrier transporting substances described above can be easily synthesized by known synthesis methods. For example, reference may be made to the method described in Japanese Publication No. 58-198425.
〜 (例示化合物(I))
上記アルデヒド(1) 2.73g(0,旧モル)と上
記ホスホネート(2) 2.70g(0,01モル)を
N、N−ジメチルホルムアミド20mQ、に加えナトリ
ウムメチラートの28%メタノール溶液2.90gを室
温で滴下した。~ (Exemplary Compound (I)) 2.73 g (0.01 mole) of the above aldehyde (1) and 2.70 g (0.01 mole) of the above phosphonate (2) were added to 20 mQ of N,N-dimethylformamide, and sodium methane was added. 2.90 g of a 28% methanol solution of Lato was added dropwise at room temperature.
滴下後室部で5時間撹拌した。反応液に水6Qmf2を
加えトルエンで抽出した後、トルエン層を水洗、乾燥し
、トルエンを除去した。少量のメタノールを加えて結晶
化し、結晶をは取、乾燥後、n−ヘキサノ、トルエン、
混合溶媒から再結晶して淡黄色収量 2.5g (64
,0%)
FD−マススペクトルで389の分子イオンピークが観
測されたことにより、目的物が合成されたことを確認し
た。After the dropwise addition, the mixture was stirred in the chamber for 5 hours. After adding 6Qmf2 of water to the reaction solution and extracting with toluene, the toluene layer was washed with water and dried to remove toluene. Crystallize by adding a small amount of methanol, peel off the crystals, dry, and add n-hexano, toluene,
Recrystallization from a mixed solvent yielded 2.5 g (64
, 0%) A molecular ion peak of 389 was observed in the FD-mass spectrum, confirming that the target product was synthesized.
次に本発明に適するキャリア発生物質としては、アゾ顔
料が好ましいが、一般には可視光から赤外光を吸収して
、フリーキャリアを発生するものであれば無機顔料およ
び有機顔料のいずれをも用いることができる。例えば無
定形セレン、三方晶形セレン、セレン−砒素合金、セレ
ン−テルル合金、硫化カドミウム等の無機顔料のほか次
の代表例で示されるような有機顔料を用いても良い。Next, as a carrier generating substance suitable for the present invention, an azo pigment is preferable, but in general, any inorganic pigment or organic pigment can be used as long as it absorbs visible light to infrared light and generates free carriers. be able to. For example, in addition to inorganic pigments such as amorphous selenium, trigonal selenium, selenium-arsenic alloy, selenium-tellurium alloy, and cadmium sulfide, organic pigments such as those shown in the following representative examples may be used.
(1) モノアゾ顔料、ビスアゾ顔料、トリスアゾ顔
料、金属錯塩アゾ顔料等のアゾ顔料
(2)ペリレン酸無水物、ペリレン酸イミド等のペリレ
ン系顔料
(3) アンスラキノン誘導体、アンスアンスロン誘
導体、ジベンズピレンキノン誘導体、ピランスロン誘導
体、ビオランスロン誘導体およびイソビオランスロン誘
導体等多環キノン系顔料
(4)インジゴ誘導体およびチオインジゴ誘il 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ンアニン等
の7タロ/アニン系顔料
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
光層か形成される。(1) Azo pigments such as monoazo pigments, bisazo pigments, trisazo pigments, metal complex azo pigments, etc. (2) Perylene pigments such as perylene acid anhydride, perylene acid imide, etc. (3) Anthraquinone derivatives, anthanthrone derivatives, dibenzpyrene Polycyclic quinone pigments such as quinone derivatives, pyranthrone derivatives, violanthrone derivatives and isoviolanthrone derivatives (4) Indigoid pigments such as indigo derivatives and thioindigo derivatives (5) 7talo/anine such as metal phthalocyanine and metal-free phthalonanine Pigment-based carrier transport substances used in the present invention do not have the ability to form a film by themselves, so they are combined with various binders to form a photosensitive layer.
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かできるが、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)ポリ塩化ヒニリデン
(7)ポリスチレン
(8)ポリビニルアセテート
(9) スチレン共重合樹脂(たとえば、スチレン−ブ
タヂエン共重合体、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(たとえ
は、塩化ヒニリデンー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
ヒニルー酢酸ビニルー無水マレイン酸共重合体
(13) /リコーン樹脂
(1,1) ンリコーンーアルキツト樹脂(15)フ
ェノール樹脂
(16) スチレン−アルキッド樹脂(17)ポリ−
N−上ニルカルバゾール(18) ポリヒニルブチラ
ール
(19)ポリヒニルホルマール
(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) Polyhynylidene chloride (7) Polystyrene (8) Polyvinyl acetate (9) Styrene copolymer resin (e.g. styrene -butadiene copolymer, styrene-methyl methacrylate copolymer, etc.) (10) Acrylonitrile copolymer resin (for example, hnylidene chloride-acrylonitrile copolymer, etc.) (11) Vinyl chloride-vinyl acetate copolymer Polymer (12) Hynyl chloride-vinyl acetate-maleic anhydride copolymer (13) / silicone resin (1,1) silicone-alkyd resin (15) phenolic resin (16) styrene-alkyd resin (17) poly-
N-onylcarbazole (18) Polyhinyl butyral (19) Polyhinyl formal (20) Polyhydroxystyrene These binders can be used alone or in a mixture of two or more.
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l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 l, and a carrier-generating layer 2 containing a carrier-generating substance as a main component and a 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M4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。As shown in FIGS. 3 and 4, this photosensitive layer M4 may be provided on the conductive support 1 via an intermediate layer 5.
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■上に直接あるいは、中間層5を介して設けても
よい。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. (2) It may be provided directly on top or 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.
また、二層構成の感光層4を構成するキャリア発生層2
は、導電性支持体lもしくはキャリア輸送層3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。Further, a carrier generation layer 2 constituting a photosensitive layer 4 having a two-layer structure
can be formed directly on the conductive support l or the carrier transport layer 3 or after providing an intermediate layer such as an adhesive layer or a barrier layer if necessary, by the following 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. as necessary.
A method of applying a dispersion obtained by mixing and dispersing a binder.
このようにして形成されるキャリア発生層2の厚さは、
0.旧〜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 2 formed in this way is
0. It is preferably from 1 to 5 μm, more preferably from 0.05 to 3 μm.
またキャリア輸送層3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°が好しい。Further, the thickness of the carrier transport layer 3 can be changed as necessary, but it is usually preferably 5 to 30 μm.
このキャリア輸送層3における組成割合は、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〜IO重
量部とするのか好しいが、微粒子状のキャリア発生物質
を分散せしめた感光層4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
用いることが好しい。The composition ratio in this carrier transport layer 3 is preferably 0.8 to IO parts by weight of the binder to 1 part by weight of the carrier transport material of the present invention. When forming layer 4, 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.
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しい。Further, when the carrier generation layer is configured as a dispersed 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.
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、表面層となるキャリア輸送層、キャ
リア発生層、単層感光層または保護層のいずれか、もし
くは複数層には感度の向上、残留電位、反復使用時の疲
労の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。The layer structure of the photoreceptor of the present invention includes a laminated structure and a single layer structure as described above, and either a carrier transport layer serving as a surface layer, a carrier generation layer, a single layer photosensitive layer, or a protective layer, or a plurality of layers. The layer may contain one or more electron-accepting substances for the purpose of improving sensitivity, reducing residual potential, and reducing fatigue during repeated use.
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、例えハホリビニルア
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, haorivinyl alcohol, ethyl cellulose, carboxymethyl cellulose, casein, etc. are used.
本発明の電子写真感光体の構成に用いられる導電性支持
体l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 l used in the construction of the electrophotographic photoreceptor of the present invention, the following are mainly used, but the 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 items.
(2)紙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 paper 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、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.
本発明に係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、スパッタリング、CVD
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, and CVD.
A vapor deposition method such as , or a coating method such as dipping, spraying, blade, or roll method may be arbitrarily used.
本発明の感光体は以上のような構成であって、後述する
ような実施例からも明らかなように帯電特性、感度特性
、画像形成特性に優れたものである。特に反復転写式電
子写真方式に供したときにも疲労劣化が少なく耐久性が
優れたものである。The photoreceptor of the present invention has the above-mentioned structure, and has excellent charging characteristics, sensitivity characteristics, and image forming characteristics, as is clear from the examples described below. In particular, it exhibits excellent durability with little fatigue deterioration even when subjected to repeated transfer electrophotography.
以下本発明の実施例を具体的に説明するが、これにより
本発明の実施態様が限定されるものではない。Examples of the present invention will be specifically described below, but the embodiments of the present invention are not limited thereby.
実施例 l
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
イン酸共重合体[エスレソクMF−10J(種水化学社
製)より成る厚さ0.1μmの中間層を設けた。Example 1 A conductive support formed by vapor-depositing aluminum on a polyester film was coated with a film made of vinyl chloride-vinyl acetate-maleic anhydride copolymer [Suresoku MF-10J (manufactured by Tanezu Kagaku Co., Ltd.) with a thickness of 0.5 mm. A 1 μm intermediate layer was provided.
その上に下記構造式で表されるジブロムアンスアンスロ
ン [モノライトレンド2 YJ (IC1社M)1重
量部とポリカーボネート樹脂「パンライトL−1250
J (音大化成社製)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lpm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 part by weight of dibrome anthronate represented by the following structural formula [Monolite Trend 2 YJ (IC1 Company M)] and polycarbonate resin "Panlite L-1250" were added.
J (manufactured by Ondai Kasei Co., Ltd.) in 100 parts by weight of 1,2-dichloroethane and dispersed in a ball mill for 24 hours. The liquid was applied to a carrier so that the film thickness after drying was lpm. A generation layer was formed.
その上にキャリア輸送物質として例示化合物(1)7.
5重量部とポリカーボネート樹脂「パンライトL −1
250J 10重量部とを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20μmになるよ
うに塗布してキャリア輸送層を形成し本発明の電子写真
感光体を作成した。Exemplary compound (1)7.
5 parts by weight and polycarbonate resin "Panlite L-1"
250J 10 parts by weight and 1,2-dichloroethane 80
The electrophotographic photoreceptor of the present invention was prepared by coating a solution dissolved in parts by weight so that the film thickness after drying was 20 μm to form a carrier transport layer.
この電子写真感光体について、静電複写紙試験装置rE
PA−8100J (川口電機製作所)を用いてダイナ
ミンク方式で電子写真特性を測定した。Regarding this electrophotographic photoreceptor, the electrostatic copying paper tester rE
The electrophotographic properties were measured using a Dynamink method using PA-8100J (Kawaguchi Electric Seisakusho).
すなわち、前記感光体の感光層表面を帯電圧−6KVで
5秒間帯電せしめた時の表面電位VA、次イでタングス
テンランプの光を感光体表面の照度が3.5(luxに
なるようにして照射し、表面電位を一600Vから一1
00vに減衰させるのに要する露光量(感度)E、::
、並びに30Qux−secの露光量で照射した後の表
面電位(残留電位)VRをそれぞれ求めた。That is, the surface potential VA when the surface of the photosensitive layer of the photoreceptor is charged for 5 seconds at a charging voltage of -6 KV, and then the light from the tungsten lamp is applied to the surface of the photoreceptor so that the illuminance of the photoreceptor surface becomes 3.5 (lux). irradiated to increase the surface potential from -600V to -11
Exposure amount (sensitivity) required to attenuate to 00v E, ::
, and the surface potential (residual potential) VR after irradiation with an exposure amount of 30 Qux-sec were determined.
また同様の測定を100回繰返して行なった。結果は、
第1表に示すとおりである。Further, similar measurements were repeated 100 times. Result is,
As shown in Table 1.
比較例(1)
キャリア輸送物質として下記構造式で示されるスチルベ
ン誘導体を用いたほかは、実施例1と同様にして比較用
感光体(1)を作成し、実施例1と同様の測定を行なっ
た。Comparative Example (1) A comparative photoreceptor (1) was prepared in the same manner as in Example 1, except that a stilbene derivative represented by the following structural formula was used as a carrier transport substance, and the same measurements as in Example 1 were carried out. Ta.
結果は第1表に示すとおりである。The results are shown in Table 1.
第1表
以上の結果から明らかなように実施例1の本発明の電子
写真感光体は、比較例(1)の感光体に比べて感度、残
留電位特性並びに繰返しの安定性において著しく優れた
ものである。As is clear from the results in Table 1 and above, the electrophotographic photoreceptor of the present invention of Example 1 was significantly superior to the photoreceptor of Comparative Example (1) in terms of sensitivity, residual potential characteristics, and repeated stability. It is.
実施例2〜10 キャリア輸送物質として例示化合物(2)、(4)。Examples 2-10 Exemplary compounds (2) and (4) as carrier transport substances.
(6)、(8)、(10)、(12)、(14)、(1
6)、(18)を用いたはがば、実施例1と同様にして
本発明の電子写真感光体を作成した。これらの電子写真
感光体について実施例1と同様にして測定を行なった。(6), (8), (10), (12), (14), (1
An electrophotographic photoreceptor of the present invention was prepared in the same manner as in Example 1 using 6) and (18). Measurements were performed on these electrophotographic photoreceptors in the same manner as in Example 1.
結果を第2表に示した。The results are shown in Table 2.
第2表
実施例 11
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下記
構造式で示されるビスアゾ顔料1重量部とポリメチルメ
タクリレ−1・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。Table 2 Example 11 1 part by weight of a bisazo pigment represented by the following structural formula and polymethyl methacrylate-1 resin "Dianal" were placed on a conductive support consisting of a polyester film laminated with aluminum foil. 0.5 parts by weight of BR-80J (manufactured by Mitsubishi Rayon Co., Ltd.) was added to 100 parts by weight of 1,2-dichloroethane and dispersed for 4 hours using a sand grinder.The resulting solution was coated 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(3)7.5
重量部とポリカーボネート樹脂「パンライトK −13
004(量大化成社製) 10重量部とを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
20μmになるように塗布し、キャリア輸送層を形成し
本発明の電子写真感光体を作成した。Next, Exemplified Compound (3) 7.5 as a carrier transport substance
Weight parts and polycarbonate resin "Panlite K-13"
A solution prepared by dissolving 10 parts by weight of 004 (manufactured by Ryotai Kasei Co., Ltd.) in 100 parts by weight of 1,2-dichloroethane is coated so that the film thickness after drying is 20 μm to form a carrier transport layer. A photographic photoreceptor was created.
この電子写真感光体について実施例1と同様にして測定
したところ第3表に示す結果を得た。This electrophotographic photoreceptor was measured in the same manner as in Example 1, and the results shown in Table 3 were obtained.
比較例(2)
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
ン誘導体を用いたほがは実施例11と同様にして比較用
感光体(2)を作成した。この比較用感光体について実
施例1と同様に測定したところ第3表に示す結果を得た
。Comparative Example (2) A comparative photoreceptor (2) was prepared in the same manner as in Example 11 using a stilbene derivative represented by the following structural formula as a carrier transporting substance. When this comparative photoreceptor was measured in the same manner as in Example 1, the results shown in Table 3 were obtained.
以上の結果から明らかなように実施例11の本発明の電
子写真感光体は、比較用感光体に比べて感度、残留電位
および繰返しの安定性において著しく優れたものである
。As is clear from the above results, the electrophotographic photoreceptor of the present invention of Example 11 is significantly superior to the comparative photoreceptor in terms of sensitivity, residual potential, and repetition stability.
実施例 12
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11体rエスレソクMF−10Jより成る厚さ0.
1.unの中間層を設けた。Example 12 A conductive support formed by vapor-depositing aluminum on a polyester film was coated with vinyl chloride-vinyl acetate-maleic anhydride 11 substance r Esresoku MF-10J with a thickness of 0.
1. An intermediate layer of un was provided.
その上にキャリア発生物質として下記構造式で表される
ビスアゾ顔料1重量部とポリカーボネート樹脂 [パン
ライトK −1300J O,5重量部とをテトラヒド
ロ7ラン100重量部に加えボールミルで24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
てキャリア発生層を形成した。On top of that, 1 part by weight of a bisazo pigment represented by the following structural formula as a carrier generating substance and 5 parts by weight of polycarbonate resin [Panlite K-1300J O] were added to 100 parts by weight of Tetrahydro 7ran and dispersed in a ball mill for 24 hours. A carrier generation layer was formed by applying the following to a dry film thickness of 0.4 μm.
次いでその上にキャリア輸送物質として例示化合物(5
)7.5重量部とポリカーボネート樹脂[パンライトK
−1300J 10重量部とをテトラヒドロフラン1
00重量部に溶解した液を乾燥後の膜厚が20μmにな
るように塗布して本発明の電子写真感光体を作成した。Next, an exemplified compound (5) was added thereon as a carrier transport substance.
) 7.5 parts by weight and polycarbonate resin [Panlite K
-10 parts by weight of 1300J and 1 part by weight of tetrahydrofuran
An electrophotographic photoreceptor of the present invention was prepared by applying a solution dissolved in 0.00 parts by weight so that the film thickness after drying was 20 μm.
この電子写真感光体を実施例1と同様にして測定したと
ころ第4表の結果を得た。When this electrophotographic photoreceptor was measured in the same manner as in Example 1, the results shown in Table 4 were obtained.
実施例 13
キャリア発生物質として下記構造式で示されるヒスアゾ
顔料を用いたほかは、実施例12と同様にして本発明の
電子写真感光体を作成した。Example 13 An electrophotographic photoreceptor of the present invention was prepared in the same manner as in Example 12, except that a hisazo pigment represented by the following structural formula was used as a carrier-generating substance.
この電子写真感光体について実施例1と同様にして測定
したところ第4表の結果を得た。When this electrophotographic photoreceptor was measured in the same manner as in Example 1, the results shown in Table 4 were obtained.
第4表
実施例 14
直径80mmの円筒状アルミニウムドラム上に塩化ビニ
ル−酢酸ビニル−無水マレイン酸共重合体「エスレック
MF−10Jより成る厚さ0.1μmの中間層をディッ
ピング法により塗布した。Table 4 Example 14 A 0.1 μm thick intermediate layer made of vinyl chloride-vinyl acetate-maleic anhydride copolymer "S-LEC MF-10J" was coated on a cylindrical aluminum drum with a diameter of 80 mm by a dipping method.
その上にジブロムアンスアンスロン 「モノライトレッ
ド2YJ1重量部とポリカーボネート樹脂[パンライト
L−1250J 1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
た液をディッピング法により塗布し膜厚1μmのキャリ
ア発生層を形成した。On top of that, 1 part by weight of Dibrom Anthron "Monolite Red 2YJ and 1 part by weight of polycarbonate resin [Panlite L-1250J] were mixed in 100 parts by weight of 1,2-dichloroethane, and the liquid was dispersed in a ball mill for 24 hours using a dipping method. A carrier generation layer having a film thickness of 1 μm was formed by coating.
更にその上にキャリア輸送物質として例示化合物(2)
7.5mff1部と下記構造式で示されるポリカーボ
ネート樹脂rZ −200J (三菱ガ゛ス化学社製)
10重量部とを1.2−ジクロルエタン80重量部に溶
解した液を同じくディッピング法により塗布して膜厚2
0μmのキャリア輸送層を形成し本発明の電子写真感光
体を作成した。Furthermore, exemplified compound (2) is added as a carrier transport substance.
7.5 mff 1 part and polycarbonate resin rZ-200J shown by the following structural formula (manufactured by Mitsubishi Gas Chemical Co., Ltd.)
A solution prepared by dissolving 10 parts by weight of the
An electrophotographic photoreceptor of the present invention was prepared by forming a carrier transport layer with a thickness of 0 μm.
この電子写真感光体を電子写真複写機ro−Bix15
50MRJに装着し、画像の複写を行なったところ原画
に忠実でコントラストが高く、かつ階調性に優れた複写
画像を得た。これは5万回繰返しても初期と同様の複写
画像が得られた。This electrophotographic photoreceptor is used in an electrophotographic copying machine ro-Bix15.
When the image was copied by attaching it to a 50MRJ, a copied image was obtained that was faithful to the original, had high contrast, and had excellent gradation. Even after repeating this process 50,000 times, a copy image similar to the initial one was obtained.
比較例(3)
キャリア輸送物質として、下記構造式で示されるヒドラ
ゾン誘導体を用いたほかは実施例14と同様にして比較
用感光体(3)を作成した。Comparative Example (3) A comparative photoreceptor (3) was prepared in the same manner as in Example 14, except that a hydrazone derivative represented by the following structural formula was used as a carrier transport substance.
この比較用感光体について実施例14と同様にして画像
の複写を行なったところ初期は実施例14と同様、良好
な複写画像を得たが、15,000コピイあたりからか
ぶりが目立ちはじめ2万コピイでは、かぶりの多いコン
トラストの低下した画像しか得られなかった。When images were copied using this comparative photoreceptor in the same manner as in Example 14, a good copy image was initially obtained as in Example 14, but fogging began to become noticeable around 15,000 copies and after 20,000 copies. However, only images with a lot of fog and reduced contrast could be obtained.
実施例 15
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
した導電性支持体上に塩化ビニル−酢酸ヒニルー無水マ
レイン酸共重合体「エスレックMF−10」より成る厚
さ0.1μmの中間層を設けた。Example 15 A 0.1 μm thick intermediate layer made of vinyl chloride-hinyl acetate-maleic anhydride copolymer "S-LEC MF-10" was provided on a conductive support made of a polyester film laminated with aluminum foil.
次いでその上にキャリア輸送物質として例示化合物(7
)7.5重量部とポリカーボネート樹脂「パンライトL
−1250J 10重量部とを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20μmに
なるように塗布してキャリア輸送層を形成し j二 。Next, an exemplary compound (7) was added thereon as a carrier transport substance.
) 7.5 parts by weight and polycarbonate resin "Panlite L"
-1250J dissolved in 80 parts by weight of 1,2-dichloroethane was applied to form a carrier transport layer so that the film thickness after drying was 20 μm.
更にその上に下記構造式で示されるキャリア発生物質1
重量部およびキャリア輸送物質として例示化合物(7)
1.5ffNt部、ポリカーボネート樹脂[パンライ
トL−,1250J 2重量部とを1,2−ジクロルエ
タン100重量部に加え24時間ボールミルで分散した
液を塗布し乾燥後の膜厚が3μmであるキャリア発生層
を設は本発明の電子写真感光体を作成した。Furthermore, a carrier generating substance 1 represented by the following structural formula is added thereto.
Exemplary compound (7) as part by weight and carrier transport substance
1.5 ffNt parts, 2 parts by weight of polycarbonate resin [Panlite L-, 1250J] were added to 100 parts by weight of 1,2-dichloroethane, and the resulting solution was dispersed in a ball mill for 24 hours to form a carrier with a film thickness of 3 μm after drying. An electrophotographic photoreceptor of the present invention was prepared by forming the layers.
この電子写真感光体について帯電圧を+6kvに変えた
ほかは、実施例1と同様にして測定したところ第5表に
示す結果を得た。This electrophotographic photoreceptor was measured in the same manner as in Example 1, except that the charging voltage was changed to +6 kV, and the results shown in Table 5 were obtained.
比較例(4)
キャリア輸送物質として、下記構造式で示されるスチル
ベン誘導体を用いたほかは、実施例15と同様にして比
較用感光体を作成した。Comparative Example (4) A comparative photoreceptor was prepared in the same manner as in Example 15, except that a stilbene derivative represented by the following structural formula was used as the carrier transport substance.
この比較用感光体について実施例15と同様にして測定
したところ第5表に示す結果を得た。When this comparative photoreceptor was measured in the same manner as in Example 15, the results shown in Table 5 were obtained.
第5表
以上の結果から明らかなように本発明の電子写真感光体
は比較用感光体に比べて感度および繰返しの安定性にお
いて極めて優れた特性を有している。As is clear from the results in Table 5 and above, the electrophotographic photoreceptor of the present invention has extremely superior characteristics in terms of sensitivity and repeated stability compared to the comparative photoreceptor.
実施例 16
アルミニウムを蒸着したポリエステルフィルム上に塩化
ヒニルー酢酸ヒニルー無水マレイン酸共重合体[エスレ
ソクMF−10Jから成る膜厚0.1μmの中間層を設
けた。Example 16 An intermediate layer having a thickness of 0.1 μm consisting of a hinyl chloride-hinyl acetate-maleic anhydride copolymer [ESRESOC MF-10J] was provided on a polyester film on which aluminum was vapor-deposited.
その上にキャリア輸送物質として下記構造式で表される
ヒスアゾ顔料1重量部とポリカーボネート樹脂 「パン
ライl−L −1250J O,5重量部とを1゜2−
ジクロルエタン100重量部に加えボールミルで24時
間分分散た液を乾燥後の膜厚が0.3μm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 part by weight of hisazo pigment represented by the following structural formula as a carrier transport substance and 5 parts by weight of polycarbonate resin "Panrye I-L-1250J O.
A carrier generation layer was formed by applying a solution prepared by adding 100 parts by weight of dichloroethane and dispersing it in a ball mill for 24 hours so that the film thickness after drying was 0.3 μm.
更にその上にキャリア輸送物質として例示化合物(9)
7.5重量部とポリカーボネート樹脂[パンライl−K
−1300J 10重量部とを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16μm
になるように塗布してキャリア輸送層を形成し本発明の
電子写真感光体を作成した。Furthermore, exemplified compound (9) is added as a carrier transport substance.
7.5 parts by weight and polycarbonate resin [Panrye l-K
-1300J 10 parts by weight dissolved in 100 parts by weight of 1,2-dichloroethane has a film thickness of 16 μm after drying.
The electrophotographic photoreceptor of the present invention was prepared by coating the powder to form a carrier transport layer.
この電子写真感光体について実施例1と同様にして測定
したところ第6表の結果を得た。When this electrophotographic photoreceptor was measured in the same manner as in Example 1, the results shown in Table 6 were obtained.
第6表
実施例 17
アルミニウムを蒸着したポリエステルフィルム上に下記
構造式で示されるキャリア発生物質1重量部とポリエス
テル樹脂 [バイロン200J (東洋紡績社製)05
重量部とを1,2−ジクロルエタン100重量部に加え
ボールミルで24時間分散した液を塗布し厚さ05μm
のキャリア発生層を形成した。Table 6 Example 17 1 part by weight of a carrier-generating substance represented by the following structural formula and a polyester resin [Vylon 200J (manufactured by Toyobo Co., Ltd.) 05] on a polyester film on which aluminum was vapor-deposited
parts by weight were added to 100 parts by weight of 1,2-dichloroethane and dispersed in a ball mill for 24 hours, and the solution was coated to a thickness of 05 μm.
A carrier generation layer was formed.
更にその上にキャリア輸送物質として例示化合物(11
) 7.5重量部をポリカーボネート樹脂「パンライl
−K −1300J 10重量部とを1.2−ジクロル
エタン100重量部に溶解した液を塗布し厚さ15μm
のキャリア輸送層を形成し本発明の電子写真感光体を作
成した。Furthermore, an exemplary compound (11) is added thereon as a carrier transport substance.
) 7.5 parts by weight of polycarbonate resin
-K -1300J 10 parts by weight dissolved in 100 parts by weight of 1,2-dichloroethane was applied to a thickness of 15 μm.
A carrier transport layer was formed to prepare an electrophotographic photoreceptor of the present invention.
この電子写真感光体について実施例1と同様にして測定
したところ第7表の結果を得た。When this electrophotographic photoreceptor was measured in the same manner as in Example 1, the results shown in Table 7 were obtained.
比較例 (5)
キャリア輸送物質として下記構造式で示されるスチルベ
ン誘導体(A)7.5重量部を用いたほかは実施例17
と同様にして比較用感光体(5)を作成した。Comparative Example (5) Example 17 except that 7.5 parts by weight of a stilbene derivative (A) represented by the following structural formula was used as a carrier transport substance.
A comparison photoreceptor (5) was prepared in the same manner as described above.
この比較用感光体について実施例と同様にして測定した
ところ第7表の結果を得た。When this comparative photoreceptor was measured in the same manner as in the examples, the results shown in Table 7 were obtained.
スチルベン誘導体(A)
第7表
実施例18
キャリア発生物質として無金属で−7りロシアニン(東
洋インキ製(株))を用いたほかは、実施例11と同様
にしてキャリア発生層を形成した。Stilbene derivative (A) Table 7 Example 18 A carrier generation layer was formed in the same manner as in Example 11, except that metal-free -7 lysyanine (manufactured by Toyo Ink Co., Ltd.) was used as the carrier generation substance.
次いでキャリア輸送物質として例示化合物(2)4.0
重量部を用いたほかは、実施例11ど同様にしてキャリ
ア輸送層を形成し本発明の感光体を得た。Next, Exemplified Compound (2) 4.0 as a carrier transport substance
A carrier transport layer was formed in the same manner as in Example 11 except that parts by weight were used to obtain a photoreceptor of the present invention.
この電子写真感光体について実施例1と同様にして測定
したところ第8表に示す結果を得た。When this electrophotographic photoreceptor was measured in the same manner as in Example 1, the results shown in Table 8 were obtained.
第8表
以上の結果から明らかなように本発明の電子写真感光体
は、比較用感光体に比べて感度、残留電位特性並びに繰
返しの安定性において著しく()れたものである。As is clear from the results in Table 8 and above, the electrophotographic photoreceptor of the present invention is significantly superior in sensitivity, residual potential characteristics, and repetition stability compared to the comparative photoreceptor.
第1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。
1 l・・・・・導電性支持体
2・・・・キャリア発生層
3・・・・・・キャリア輸送層
4・・・・・・感光層
5・・・・・・中間層
6・・・・・・キャリア輸送物質を含有する層7・・・
・・・キャリア発生物質
8・・・・・・保護層1 to 6 are sectional views showing examples of the mechanical structure of the photoreceptor of the present invention, respectively. 1 L... Conductive support 2... Carrier generation layer 3... Carrier transport layer 4... Photosensitive layer 5... Intermediate layer 6... ...Layer 7 containing a carrier transport substance...
...Carrier generating substance 8...Protective layer
Claims (1)
リールアミン誘導体の少なくともひとつを含有する感光
層を有することを特徴とする電子写真感光体。 一般式〔 I 〕 ▲数式、化学式、表等があります▼ 〔但し、式中Ar_1、Ar_2は置換、未置換のアリ
ール基を表し、Ar_3は置換、未置換のアリーレン基
を表し、R_1、R_2、R_3、R_4、R_5、R
_6、R_7、R_8は、各々同じでも異なっていても
よく、水素原子、ハロゲン原子、置換、未置換のアルキ
ル基、置換、未置換のアルコキシ基、置換、未置換のア
リール基、置換、未置換のアリールオキシ基、置換アミ
ノ基を表す。 Xは酸素原子、硫黄原子、>N−R_9(R_9は、水
素原子、置換、未置換のアルキル基を表す)を表す。〕[Scope of Claims] An electrophotographic photoreceptor comprising a photosensitive layer containing at least one triarylamine derivative represented by the following general formula [I] on a conductive support. General formula [I] ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [However, in the formula, Ar_1 and Ar_2 represent a substituted or unsubstituted aryl group, Ar_3 represents a substituted or unsubstituted arylene group, R_3, R_4, R_5, R
_6, R_7, and R_8 may each be the same or different, and are hydrogen atom, halogen atom, substituted or unsubstituted alkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryl group, substituted or unsubstituted represents an aryloxy group or a substituted amino group. X represents an oxygen atom, a sulfur atom, or >N-R_9 (R_9 represents a hydrogen atom or a substituted or unsubstituted alkyl group). ]
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP16553788A JPH0213962A (en) | 1988-07-01 | 1988-07-01 | Electrophotographic sensitive body |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP16553788A JPH0213962A (en) | 1988-07-01 | 1988-07-01 | Electrophotographic sensitive body |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH0213962A true JPH0213962A (en) | 1990-01-18 |
Family
ID=15814271
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP16553788A Pending JPH0213962A (en) | 1988-07-01 | 1988-07-01 | Electrophotographic sensitive body |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH0213962A (en) |
-
1988
- 1988-07-01 JP JP16553788A patent/JPH0213962A/en active Pending
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