JPH04225363A - Photosensitive body - Google Patents
Photosensitive bodyInfo
- Publication number
- JPH04225363A JPH04225363A JP41781790A JP41781790A JPH04225363A JP H04225363 A JPH04225363 A JP H04225363A JP 41781790 A JP41781790 A JP 41781790A JP 41781790 A JP41781790 A JP 41781790A JP H04225363 A JPH04225363 A JP H04225363A
- Authority
- JP
- Japan
- Prior art keywords
- photoreceptor
- aminobiphenyl
- chemical formula
- parts
- layer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000126 substance Substances 0.000 claims abstract description 37
- 125000000217 alkyl group Chemical group 0.000 claims abstract 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract 2
- 125000001424 substituent group Chemical group 0.000 claims abstract 2
- 108091008695 photoreceptors Proteins 0.000 claims description 58
- -1 aminobiphenyl compound Chemical class 0.000 claims description 32
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 125000005309 thioalkoxy group Chemical group 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 31
- 230000035945 sensitivity Effects 0.000 abstract description 9
- TWBPWBPGNQWFSJ-UHFFFAOYSA-N 2-phenylaniline Chemical group NC1=CC=CC=C1C1=CC=CC=C1 TWBPWBPGNQWFSJ-UHFFFAOYSA-N 0.000 abstract description 4
- 239000002800 charge carrier Substances 0.000 abstract description 3
- 239000000758 substrate Substances 0.000 abstract description 3
- 239000010410 layer Substances 0.000 description 49
- 229920005989 resin Polymers 0.000 description 21
- 239000011347 resin Substances 0.000 description 21
- 239000011230 binding agent Substances 0.000 description 17
- 239000000049 pigment Substances 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 10
- 238000000034 method Methods 0.000 description 9
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 102100036725 Epithelial discoidin domain-containing receptor 1 Human genes 0.000 description 7
- 101710131668 Epithelial discoidin domain-containing receptor 1 Proteins 0.000 description 7
- 239000000975 dye Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 238000010586 diagram Methods 0.000 description 5
- 239000004925 Acrylic resin Substances 0.000 description 4
- 229920000178 Acrylic resin Polymers 0.000 description 4
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 229910052711 selenium Inorganic materials 0.000 description 4
- 239000011669 selenium Substances 0.000 description 4
- 239000002356 single layer Substances 0.000 description 4
- 229920001187 thermosetting polymer Polymers 0.000 description 4
- 239000011787 zinc oxide Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-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
- 229910052980 cadmium sulfide Inorganic materials 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 3
- 229910003437 indium oxide Inorganic materials 0.000 description 3
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 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 3
- 229920001225 polyester resin Polymers 0.000 description 3
- 239000004645 polyester resin Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000011241 protective layer Substances 0.000 description 3
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 3
- 229910001887 tin oxide Inorganic materials 0.000 description 3
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 2
- QNLZIZAQLLYXTC-UHFFFAOYSA-N 1,2-dimethylnaphthalene Chemical compound C1=CC=CC2=C(C)C(C)=CC=C21 QNLZIZAQLLYXTC-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- 229920000134 Metallised film Polymers 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical compound C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 description 2
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical class C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 150000002894 organic compounds Chemical class 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
- 229920005668 polycarbonate resin Polymers 0.000 description 2
- 239000004431 polycarbonate resin Substances 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical class C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 2
- 229920005992 thermoplastic resin Polymers 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 description 1
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 1
- VYWYYJYRVSBHJQ-UHFFFAOYSA-N 3,5-dinitrobenzoic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 VYWYYJYRVSBHJQ-UHFFFAOYSA-N 0.000 description 1
- DNXUGBMARDFRGG-UHFFFAOYSA-N 3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile Chemical compound O=C1C=CC(=O)C(C#N)=C1C#N DNXUGBMARDFRGG-UHFFFAOYSA-N 0.000 description 1
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 1
- 235000000177 Indigofera tinctoria Nutrition 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- 229910001370 Se alloy Inorganic materials 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229920002433 Vinyl chloride-vinyl acetate copolymer Polymers 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021417 amorphous silicon Inorganic materials 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- DQXBYHZEEUGOBF-UHFFFAOYSA-N but-3-enoic acid;ethene Chemical compound C=C.OC(=O)CC=C DQXBYHZEEUGOBF-UHFFFAOYSA-N 0.000 description 1
- QHIWVLPBUQWDMQ-UHFFFAOYSA-N butyl prop-2-enoate;methyl 2-methylprop-2-enoate;prop-2-enoic acid Chemical compound OC(=O)C=C.COC(=O)C(C)=C.CCCCOC(=O)C=C QHIWVLPBUQWDMQ-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
- 229920002678 cellulose Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- ZXJXZNDDNMQXFV-UHFFFAOYSA-M crystal violet Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1[C+](C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 ZXJXZNDDNMQXFV-UHFFFAOYSA-M 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 239000005038 ethylene vinyl acetate Substances 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 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
- 229920000554 ionomer Polymers 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 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
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 229920002382 photo conductive polymer Polymers 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- INAAIJLSXJJHOZ-UHFFFAOYSA-N pibenzimol Chemical compound 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
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 150000003071 polychlorinated biphenyls Chemical group 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 229940043267 rhodamine b Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 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
- 239000001016 thiazine dye Substances 0.000 description 1
- 239000001003 triarylmethane dye Substances 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 239000001018 xanthene dye Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Abstract
Description
【０００１】0001
【産業上の利用分野】本発明は新規なアミノビフェニル
化合物を含有する感光層を有する感光体に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a photoreceptor having a photosensitive layer containing a novel aminobiphenyl compound.
【０００２】0002
【従来の技術】一般に電子写真においては、感光体の感
光層表面に帯電、露光を行なって静電潜像を形成し、こ
れを現像剤で現像し、可視化させ、その可視像をそのま
ま直接感光体上に定着させて複写像を得る直接方式、ま
た感光体上の可視像を紙などの転写材上に転写し、その
転写像を定着させて複写像を得る粉像転写方式あるいは
感光体上の静電潜像を転写紙上に転写し、転写紙上の静
電潜像を現像、定着する潜像転写方式等が知られている
。この種の電子写真法に使用される感光体の感光層を構
成する材料として、従来よりセレン、硫化カドミウム、
酸化亜鉛等の無機光導電性材料が知られている。[Prior Art] Generally, in electrophotography, the surface of the photosensitive layer of a photoreceptor is charged and exposed to form an electrostatic latent image, which is developed with a developer to make it visible, and the visible image is directly transferred as it is. A direct method that obtains a copy image by fixing it on a photoreceptor, a powder image transfer method or a photosensitive method that transfers the visible image on the photoreceptor onto a transfer material such as paper and fixes the transferred image to obtain a copy image. 2. Description of the Related Art A latent image transfer method is known in which an electrostatic latent image on a body is transferred onto a transfer paper, and the electrostatic latent image on the transfer paper is developed and fixed. Conventionally, selenium, cadmium sulfide,
Inorganic photoconductive materials such as zinc oxide are known.
【０００３】これらの光導電性材料は数多くの利点、例
えば暗所で電荷の逸散が少ないこと、あるいは光照射に
よって速やかに電荷を逸散できることなどの利点を持っ
ている反面、各種の欠点を持っている。例えば、セレン
系感光体では、製造する条件が難しく、製造コストが高
く、また熱や機械的な衝撃に弱いため取り扱いに注意を
要する。硫化カドミウム系感光体や酸化亜鉛感光体では
、多湿の環境下で安定した感度が得られない点や、増感
剤として添加した色素がコロナ帯電による帯電劣化や露
光による光退色を生じるため、長期に渡って安定した特
性を与えることができないという欠点を有している。Although these photoconductive materials have many advantages, such as less charge dissipation in the dark and the ability to quickly dissipate charge when irradiated with light, they also have various disadvantages. have. For example, selenium-based photoreceptors require difficult manufacturing conditions, high manufacturing costs, and must be handled with care because they are susceptible to heat and mechanical shock. Cadmium sulfide photoreceptors and zinc oxide photoreceptors do not provide stable sensitivity in humid environments, and the dyes added as sensitizers cause charging deterioration due to corona charging and photobleaching due to exposure, so they cannot be used for long periods of time. It has the disadvantage that it cannot provide stable characteristics over a long period of time.
【０００４】一方、ポリビニルカルバゾールをはじめと
する各種の有機光導電性ポリマーが提案されてきたが、
これらのポリマーは、前述の無機系光導電材料に比べ、
成膜性、軽量性などの点で優れているが、未だ充分な感
度、耐久性および環境変化による安定性の点で無機系光
導電材料に比べ劣っている。また低分子量の有機光導電
性化合物は、併用する結着材の種類、組成比等を選択す
ることにより被膜の物性あるいは電子写真特性を制御す
ることができる点では好ましいものであるが、結着材と
併用されるため、結着材に対する高い相溶性が要求され
る。On the other hand, various organic photoconductive polymers including polyvinylcarbazole have been proposed;
These polymers, compared to the above-mentioned inorganic photoconductive materials,
Although they are excellent in terms of film formability and light weight, they are still inferior to inorganic photoconductive materials in terms of sufficient sensitivity, durability, and stability against environmental changes. In addition, low molecular weight organic photoconductive compounds are preferable in that the physical properties or electrophotographic properties of the film can be controlled by selecting the type and composition ratio of the binder used in combination; Since it is used in combination with materials, high compatibility with the binder is required.
【０００５】これらの高分子量および低分子量の有機光
導電性化合物を結着材樹脂中に分散させた感光体は、キ
ャリアのトラップが多いため残留電位が大きく、感度が
低い等の欠点を有する。そのため光導電性化合物に電荷
輸送材料を配合して前記欠点を解決することが提案され
ている。Photoreceptors in which these high-molecular-weight and low-molecular-weight organic photoconductive compounds are dispersed in a binder resin have drawbacks such as high residual potential and low sensitivity due to a large number of carrier traps. Therefore, it has been proposed to incorporate a charge transporting material into a photoconductive compound to solve the above-mentioned drawbacks.
【０００６】また、光導電性機能の電荷発生機能と電荷
輸送機能とをそれぞれ別個の物質に分担させるようにし
た機能分離型感光体が提案されている。このような機能
分離型感光体において、電荷輸送層に使用される電荷輸
送材料としては多くの有機化合物が挙げられているが実
際には種々の問題点がある。例えば米国特許３，１８９
，４４７号公報に記載されている２，５‐ビス（Ｐ‐ジ
エチルアミノフェニル）１，３，４‐オキサジアゾール
は、結着材に対する相溶性が低く結晶が析出しやすい。
特開平２−１７８６６８号公報に記載されている下記化
合物は、結着材に対する相溶性は良好であるが、繰り返
し使用Further, a functionally separated photoreceptor has been proposed in which the charge generation function and the charge transport function of the photoconductive function are assigned to separate substances. In such functionally separated type photoreceptors, many organic compounds have been mentioned as charge transport materials used in the charge transport layer, but in practice they have various problems. For example, U.S. Patent 3,189
, 447, 2,5-bis(P-diethylaminophenyl) 1,3,4-oxadiazole has low compatibility with binders and tends to precipitate crystals. The following compounds described in JP-A-2-178668 have good compatibility with binders, but cannot be used repeatedly.
【化２】
した場合に感度変化が生じる。特開平１−１１８１４１
号公報に記載されている下記ベンジジン系化合物は、結
着材に対する相溶性が低く結晶が析出しやすい。[Chemical formula 2] When this occurs, a change in sensitivity occurs. JP 1-118141
The benzidine compounds described in the above publication have low compatibility with binders and tend to precipitate crystals.
【化３】
また、特開昭５４−５９１４３号公報に記載されている
ヒドラゾン化合物は、残留電位特性は比較的良好である
が、帯電能、繰り返し特性が劣るという欠点を有する。
このように感光体を作製する上で実用的に好ましい特性
を有する低分子量の有機化合物はほとんど無いのが実状
である。##STR00003## Further, the hydrazone compound described in JP-A-54-59143 has relatively good residual potential characteristics, but has the disadvantage of poor charging ability and repeatability. The reality is that there are almost no low-molecular-weight organic compounds that have practically desirable properties for producing photoreceptors.
【０００７】[0007]
【発明が解決しようとする課題】本発明の目的は、先に
述べた従来の感光体のもつ種々の欠点を解消した電子写
真感光体を提供することにある。本発明の他の目的は製
造が容易で、且つ比較的安価で耐久性にも優れた新規な
感光体を提供することにある。SUMMARY OF THE INVENTION An object of the present invention is to provide an electrophotographic photoreceptor that overcomes the various drawbacks of the conventional photoreceptors mentioned above. Another object of the present invention is to provide a novel photoreceptor that is easy to manufacture, relatively inexpensive, and has excellent durability.
【０００８】[0008]
【課題を解決するための手段】本発明は導電性支持体上
に上記一般式［Ｉ］ （化１）で示されるアミノビフェ
ニル化合物を含有する感光層を有する感光体に関する。
一般式［Ｉ］ で示されるアミノビフェニル化合物は結
着材に対する相溶性が高く、ベンジジン系化合物の欠点
である低溶解性を解消し、電子写真法において要求され
る条件を十分満足しうる感光体を提供する。[Means for Solving the Problems] The present invention relates to a photoreceptor having a photosensitive layer containing an aminobiphenyl compound represented by the above general formula [I] (Chemical formula 1) on a conductive support. The aminobiphenyl compound represented by the general formula [I] has high compatibility with the binder, eliminates the low solubility that is a drawback of benzidine compounds, and provides a photoreceptor that fully satisfies the conditions required in electrophotography. I will provide a.
【０００９】本発明において感光層に含有させる前記一
般式［Ｉ］ で表わされるアミノビフェニル化合物は、
例えば下記一般式［ＩＩ］（化４）で表わされるジ沃化
ビフェニル誘導体と下記一般式［ＩＩＩ］ （化５）で
表わされるジフェニルアミン誘導体を反応させることに
よって製造される。In the present invention, the aminobiphenyl compound represented by the general formula [I] contained in the photosensitive layer is
For example, it is produced by reacting a diiodinated biphenyl derivative represented by the following general formula [II] (Chemical formula 4) with a diphenylamine derivative represented by the following general formula [III] (Chemical formula 5).
【化４】 〔式中、Ｒ１ ，Ｒ２ は前記と同じ〕[C4] [In the formula, R1 and R2 are the same as above]
【化５】
〔式中、Ｒ３ ，Ｒ４ ，Ｒ５ ，Ｒ６は前記と同じ〕
[In the formula, R3, R4, R5, and R6 are the same as above]
【００１０】本発明の一般式［Ｉ］ で表わされるアミ
ノビフェニル化合物の好ましい具体例としては例えば次
の構造式を有するものがあげられるが、これらに限定さ
れるものではない。Preferred specific examples of the aminobiphenyl compound represented by the general formula [I] of the present invention include those having the following structural formula, but are not limited thereto.
【化６】[C6]
【化７】[C7]
【化８】[Chemical formula 8]
【化９】[Chemical formula 9]
【化１０】[Chemical formula 10]
【化１１】[Chemical formula 11]
【化１２】[Chemical formula 12]
【００１１】本発明の感光体は前記一般式［Ｉ］ で示
されるアミノビフェニル化合物を１種または２種以上含
有する感光層を有する。各種の形態の感光体は知られて
いるが、本発明の感光体のそのいずれの感光体で有って
もよい。たとえば、支持体上に電荷発生材料と、アミノ
ビフェニル化合物を樹脂バインダーに分散させて成る感
光層を設けた単層感光体や、支持体上に電荷発生材料を
主成分とする電荷発生層を設け、その上に電荷輸送層を
設けた所謂積層感光体等がある。本発明のアミノビフェ
ニル化合物は光導電性物質であるが、電荷輸送材料とし
て作用し、光を吸収することにより発生した電荷担体を
、極めて効率よく輸送することができる。The photoreceptor of the present invention has a photosensitive layer containing one or more aminobiphenyl compounds represented by the general formula [I]. Various types of photoreceptors are known, and the photoreceptor of the present invention may be any of them. For example, a single-layer photoreceptor has a photosensitive layer formed by dispersing a charge-generating material and an aminobiphenyl compound in a resin binder on a support, or a single-layer photoreceptor has a charge-generating layer mainly composed of a charge-generating material on a support. There are also so-called laminated photoreceptors in which a charge transport layer is provided thereon. Although the aminobiphenyl compound of the present invention is a photoconductive substance, it acts as a charge transport material and can transport charge carriers generated by absorbing light extremely efficiently.
【００１２】単層型感光体を作製するためには、電荷発
生材料の微粒子を樹脂溶液もしくは、電荷輸送材料と樹
脂を溶解した溶液中に分散せしめ、これを導電性支持体
上に塗布乾燥すればよい。この時の感光層の厚さは３〜
３０μｍ、好ましくは５〜２０μｍがよい。使用する電
荷発生材料の量が少な過ぎると感度が悪く、多過ぎると
帯電性が悪くなったり、感光層の機械的機強度が弱くな
ったりし、感光層中に占める割合は樹脂１重量部に対し
て０．０１〜３重量部、好ましくは０．２〜２重量部の
範囲がよい。In order to produce a single-layer type photoreceptor, fine particles of a charge generating material are dispersed in a resin solution or a solution containing a charge transporting material and a resin, and this is coated on a conductive support and dried. Bye. The thickness of the photosensitive layer at this time is 3~
The thickness is preferably 30 μm, preferably 5 to 20 μm. If the amount of the charge generating material used is too small, the sensitivity will be poor, and if it is too large, the charging property will be poor and the mechanical strength of the photosensitive layer will be weakened. The amount is preferably 0.01 to 3 parts by weight, preferably 0.2 to 2 parts by weight.
【００１３】積層型感光体を作製するには、導電性支持
体上に電荷発生材料を真空蒸着するか、あるいは、アミ
ン等の溶媒に溶解せしめて塗布するか、顔料を適当な溶
剤もしくは必要があればバインダー樹脂を溶解させた溶
液中に分散させて作製した塗布液を塗布乾燥した後、そ
の上に電荷輸送材料およびバインダーを含む溶液を塗布
乾燥して得られる。このときの電荷発生層の厚みは４μ
ｍ以下、好ましくは２μｍ以下がよく、電荷輸送層の厚
みは３〜３０μｍ、好ましくは５〜２０μｍがよい。電
荷輸送層中の電荷輸送材料の割合はバインダー樹脂１重
量部に対して０．２〜２重量部、好ましくは、０．３〜
１．３重量部である。[0013] To produce a laminated photoreceptor, a charge-generating material is vacuum-deposited on a conductive support, or it is dissolved in a solvent such as amine and coated, or a pigment is coated in a suitable solvent or as necessary. It can be obtained by coating and drying a coating liquid prepared by dispersing a binder resin in a solution, if any, and then coating and drying a solution containing a charge transporting material and a binder thereon. The thickness of the charge generation layer at this time was 4μ.
m or less, preferably 2 μm or less, and the thickness of the charge transport layer is preferably 3 to 30 μm, preferably 5 to 20 μm. The ratio of the charge transport material in the charge transport layer is 0.2 to 2 parts by weight, preferably 0.3 to 2 parts by weight, per 1 part by weight of the binder resin.
It is 1.3 parts by weight.
【００１４】本発明の感光体はバインダー樹脂とともに
、ハロゲン化パラフィン、ポリ塩化ビフェニル、ジメチ
ルナフタレン、ジブチルフタレート、０‐ターフェニル
などの可塑剤やクロラニル、テトラシアノエチレン、２
，４，７‐トリニトロフルオレノン、５，６‐ジシアノ
ベンゾキノン、テトラシアノキノジメタン、テトラクロ
ル無水フタル酸、３，５‐ジニトロ安息香酸等の電子吸
引性増感剤、メチルバイオレット、ローダミンＢ、シア
ニン染料、ピリリウム塩、チアピリリウム塩等の増感剤
を使用してもよい。In addition to the binder resin, the photoreceptor of the present invention contains plasticizers such as halogenated paraffin, polychlorinated biphenyl, dimethylnaphthalene, dibutyl phthalate, and 0-terphenyl, as well as chloranil, tetracyanoethylene, and 0-terphenyl.
, 4,7-trinitrofluorenone, 5,6-dicyanobenzoquinone, tetracyanoquinodimethane, tetrachlorophthalic anhydride, 3,5-dinitrobenzoic acid and other electron-withdrawing sensitizers, methyl violet, rhodamine B, cyanine Sensitizers such as dyes, pyrylium salts, thiapyrylium salts, etc. may also be used.
【００１５】また、酸化防止剤や紫外線吸収剤、分散助
剤、沈降防止剤等も適宜使用してもよい。[0015] Furthermore, antioxidants, ultraviolet absorbers, dispersion aids, antisettling agents, etc. may also be used as appropriate.
【００１６】本発明において使用される電気絶縁性のバ
インダー樹脂としては、電気絶縁性であるそれ自体公知
の熱可塑性樹脂あるいは熱硬化性樹脂や光硬化性樹脂や
光導電性樹脂等の結着剤を使用できる。適当な結着剤樹
脂の例は、これに限定されるものではないが、飽和ポリ
エステル樹脂、ポリアミド樹脂、アクリル樹脂、エチレ
ン‐酢酸ビニル樹脂、イオン架橋オレフィン共重合体（
アイオノマー）、スチレン‐ブタジエンブロック共重合
体、ポリカーボネート、塩化ビニル‐酢酸ビニル共重合
体、セルロースエステル、ポリイミド、スチロール樹脂
等の熱可塑性樹脂；エポキシ樹脂、ウレタン樹脂、シリ
コーン樹脂、フェノール樹脂、メラミン樹脂、キシレン
樹脂、アルキッド樹脂、熱硬化アクリル樹脂等の熱硬化
性樹脂；光硬化性樹脂；ポリビニルカルバゾール、ポリ
ビニルピレン、ポリビニルアントラセン、ポリビニルピ
ロール等の光導電性樹脂である。これらは単独で、また
は組合せて使用することができる。これらの電気絶縁性
樹脂は単独で測定して１×１０１２Ω・ｃｍ以上の体積
抵抗を有することが望ましい。The electrically insulating binder resin used in the present invention includes electrically insulating binders such as thermoplastic resins, thermosetting resins, photocurable resins, and photoconductive resins, which are known per se. can be used. Examples of suitable binder resins include, but are not limited to, saturated polyester resins, polyamide resins, acrylic resins, ethylene-vinyl acetate resins, ionically crosslinked olefin copolymers (
thermoplastic resins such as ionomers), styrene-butadiene block copolymers, polycarbonates, vinyl chloride-vinyl acetate copolymers, cellulose esters, polyimides, and styrene resins; epoxy resins, urethane resins, silicone resins, phenolic resins, melamine resins, These include thermosetting resins such as xylene resins, alkyd resins, and thermosetting acrylic resins; photocurable resins; photoconductive resins such as polyvinylcarbazole, polyvinylpyrene, polyvinylanthracene, and polyvinylpyrrole. These can be used alone or in combination. It is desirable that these electrically insulating resins have a volume resistivity of 1×10 12 Ω·cm or more when measured alone.
【００１７】電荷発生材料としては、ビスアゾ系顔料、
トリアリールメタン系染料、チアジン系染料、オキサジ
ン系染料、キサンテン系染料、シアニン系色素、スチリ
ル系色素、ピリリウム系染料、アゾ系顔料、キナクリド
ン系顔料、インジゴ系顔料、ペリレン系顔料、多環キノ
ン系顔料、ビスベンズイミダゾール系顔料、インダスロ
ン系顔料、スクアリウム塩系顔料、アズレン系色素、フ
タロシアニン系顔料等の有機物質や、セレン、セレン・
テルル、セレン・砒素などのセレン合金、硫化カドミウ
ム、セレン化カドミウム、酸化亜鉛、アモルファスシリ
コン等の無機物質が挙げられる。これ以外でも、光を吸
収し極めて高い確率で電荷担体を発生する材料であれば
、いずれの材料であっても使用することができる。As the charge generating material, bisazo pigments,
Triarylmethane dyes, thiazine dyes, oxazine dyes, xanthene dyes, cyanine dyes, styryl dyes, pyrylium dyes, azo pigments, quinacridone pigments, indigo pigments, perylene pigments, polycyclic quinone dyes Organic substances such as pigments, bisbenzimidazole pigments, indathrone pigments, squalium salt pigments, azulene pigments, and phthalocyanine pigments, selenium,
Examples include inorganic substances such as tellurium, selenium alloys such as selenium and arsenic, cadmium sulfide, cadmium selenide, zinc oxide, and amorphous silicon. In addition to these materials, any material can be used as long as it absorbs light and generates charge carriers with an extremely high probability.
【００１８】本発明の感光体に用いられる導電性支持体
としては、銅、アルミニウム、銀、鉄、亜鉛、ニッケル
等の金属や合金の箔ないしは板をシート状又はドラム状
にしたものが使用され、あるいはこれらの金属を、プラ
スチックフィルム等に真空蒸着、無電解メッキしたもの
、あるいは導電性ポリマー、酸化インジウム、酸化錫等
の導電性化合物の層を同じく紙あるいはプラスチックフ
ィルムなどの支持体上に塗布もしくは蒸着によって設け
られたものが用いられる。As the conductive support used in the photoreceptor of the present invention, a sheet or drum-shaped foil or plate of metal or alloy such as copper, aluminum, silver, iron, zinc, or nickel is used. , or these metals are vacuum-deposited or electrolessly plated onto a plastic film, etc., or a layer of a conductive compound such as a conductive polymer, indium oxide, or tin oxide is coated on a support such as paper or a plastic film. Alternatively, one provided by vapor deposition is used.
【００１９】本発明のアミノビフェニル化合物を用いた
感光体の構成例を図１から図５に模式的に示す。図１は
、基体（１）上に光導電性材料（３）と電荷輸送材料（
２）を結着剤に配合した感光層（４）が形成された感光
体であり、電荷輸送材料として本発明のアミノビフェニ
ル化合物が用いられている。なお、以下図２〜図５にお
ける符号２及び３は上記と同意義を有する。図２は、感
光層として電荷発生層（６）と、電荷輸送層（５）を有
する機能分離型感光体であり、電荷発生層（６）の表面
に電荷輸送層（５）が形成されている。電荷輸送層（５
）中に本発明のアミノビフェニル化合物が配合されてい
る。図３は、図２と同様に電荷発生層（６）と、電荷輸
送層（５）を有する機能分離型感光体であるが、図２と
は逆に電荷輸送層（５）の表面に電荷発生層（６）が形
成されている。Examples of the structure of a photoreceptor using the aminobiphenyl compound of the present invention are schematically shown in FIGS. 1 to 5. Figure 1 shows a photoconductive material (3) and a charge transport material (
This is a photoreceptor in which a photosensitive layer (4) containing 2) as a binder is formed, and the aminobiphenyl compound of the present invention is used as a charge transport material. Note that the symbols 2 and 3 in FIGS. 2 to 5 below have the same meanings as above. FIG. 2 shows a functionally separated photoreceptor having a charge generation layer (6) and a charge transport layer (5) as photosensitive layers, and the charge transport layer (5) is formed on the surface of the charge generation layer (6). There is. Charge transport layer (5
) contains the aminobiphenyl compound of the present invention. FIG. 3 shows a functionally separated photoreceptor having a charge generation layer (6) and a charge transport layer (5) as in FIG. 2, but contrary to FIG. A generation layer (6) is formed.
【００２０】図４は、図１の感光体の表面にさらに表面
保護層（７）を設けたものであり、感光層（４）は電荷
発生層（６）と、電荷輸送層（５）を有する機能分離型
感光体であってもよい。表面保護層に用いられる材料と
しては、アクリル樹脂、ポリアリール樹脂、ポリカーボ
ネート樹脂、ウレタン樹脂などのポリマーをそのまま、
または酸化スズや酸化インジウムなどの低抵抗化合物を
分散させたものなどが適当である。図５は、基体（１）
と感光層（４）の間に中間層（８）を設けたものであり
、中間層（８）は接着性の改良、塗工性の向上、基体の
保護、基体からの感光層への電荷注入性改善のために設
けることができる。FIG. 4 shows the photoreceptor shown in FIG. 1 further provided with a surface protective layer (7) on its surface, and the photosensitive layer (4) has a charge generation layer (6) and a charge transport layer (5). It may also be a functionally separated photoreceptor having the following functions. Materials used for the surface protective layer include polymers such as acrylic resin, polyaryl resin, polycarbonate resin, and urethane resin.
Alternatively, a material in which a low resistance compound such as tin oxide or indium oxide is dispersed is suitable. Figure 5 shows the base (1)
An intermediate layer (8) is provided between the photosensitive layer (4) and the photosensitive layer (4). It can be provided to improve injectability.
【００２１】中間層に用いられる材料としては、ポリイ
ミド、ポリアミド、ニトロセルロース、ポリビニルブチ
ラール、ポリビニルアルコールなどのポリマーをそのま
ま、または酸化スズや酸化インジウムなどの低抵抗化合
物を分散させたもの、酸化アルミニウム、酸化亜鉛、酸
化ケイ素などの蒸着膜等が適当である。また中間層の膜
厚は、１μｍ以下が望ましい。Materials used for the intermediate layer include polymers such as polyimide, polyamide, nitrocellulose, polyvinyl butyral, and polyvinyl alcohol as they are, or in which low-resistance compounds such as tin oxide and indium oxide are dispersed, aluminum oxide, Vapor deposited films of zinc oxide, silicon oxide, etc. are suitable. Further, the thickness of the intermediate layer is preferably 1 μm or less.
【００２２】（合成例）下記式［ＩＶ］（化１３）で表
されるジヨードビフェニル化合物(Synthesis example) Diiodobiphenyl compound represented by the following formula [IV] (Chemical formula 13)
【化１３】
１４．０重量部、ジフェニルアミン７．６重量部、炭酸
カリ５．０重量部、及び銅０．７重量部、をニトロベン
ゼン３０ｍｌ中１８０〜１９０℃で加熱、反応させた。
反応後メタノールを注加し、結晶を析出させた。その後
、析出物を濾過し、メタノール洗浄し、シリカゲルでカ
ラム精製を行い下記式（１）（化１４）で表わされる白
色結晶１１．５重量部を得た（収率７０％）。元素分析
は以下の通りである。
Ｃ
（％） Ｈ （％） Ｎ （％）
計算値 ８３．２１
５．８４ ５．１１
実測値 ８３．１１ ５．９０
５．１３embedded image 14.0 parts by weight, 7.6 parts by weight of diphenylamine, 5.0 parts by weight of potassium carbonate, and 0.7 parts by weight of copper were heated and reacted in 30 ml of nitrobenzene at 180 to 190°C. After the reaction, methanol was added to precipitate crystals. Thereafter, the precipitate was filtered, washed with methanol, and purified by column using silica gel to obtain 11.5 parts by weight of white crystals represented by the following formula (1) (Chemical formula 14) (yield: 70%). Elemental analysis is as follows. C
(%) H (%) N (%)
Calculated value 83.21
5.84 5.11
Actual value 83.11 5.90
5.13
【化１４】[Chemical formula 14]
【００２３】[0023]
【実施例】下記実施例において、特に断らない限り、「
部」は「重量部」である。
（実施例１）下記一般式［Ａ］ 〔化１５〕で表わされ
るビスアゾ化合物[Example] In the following example, unless otherwise specified, "
"Parts" are "parts by weight." (Example 1) Bisazo compound represented by the following general formula [A] [Chemical formula 15]
【化１５】
０．４５部、ポリエステル樹脂（バイロン２００；東洋
紡績社製）０．４５部をシクロヘキサノン５０部ととも
にサンドグラインダーにより分散させた。得られたビス
アゾ化合物の分散物を厚さ１００μｍのアルミ化マイラ
ー上にフィルムアプリケーターを用いて、乾燥膜厚が０
．３ｇ／ｍ２ となる様に塗布した後乾燥させた。この
ようにして得られた電荷発生層の上にアミノビフェニル
化合物〔化６の（１）〕７０部およびポリカーボネイト
樹脂（Ｋ−１３００；帝人化成社製）７０部を１，４ジ
オキサン４００部に溶解した溶液を乾燥膜厚が１６μｍ
になるように塗布し、電荷輸送層を形成した。この様に
して、２層からなる感光層を有する電子写真感光体を得
た。こうして得られた感光体を市販の電子写真複写機（
ＥＰ−４７０Ｚ；ミノルタカメラ社製）を用い、−６Ｋ
Ｖでコロナ帯電させ、初期表面電位Ｖｏ （Ｖ）、初期
電位を１／２にするために要した露光量Ｅ１／２ （ｌ
ｕｘ ・ｓｅｃ ）、および１秒間暗中に放置したとき
の初期電位の減衰率ＤＤＲ１ （％）を測定した。embedded image 0.45 parts of polyester resin (Vylon 200; manufactured by Toyobo Co., Ltd.) and 0.45 parts of polyester resin were dispersed together with 50 parts of cyclohexanone using a sand grinder. The obtained bisazo compound dispersion was applied onto a 100 μm thick aluminized mylar using a film applicator to give a dry film thickness of 0.
．． It was applied to a weight of 3 g/m2 and then dried. On the thus obtained charge generation layer, 70 parts of an aminobiphenyl compound [Chemical formula 6 (1)] and 70 parts of polycarbonate resin (K-1300; manufactured by Teijin Chemicals) were dissolved in 400 parts of 1,4 dioxane. The dried solution has a dry film thickness of 16 μm.
A charge transport layer was formed. In this way, an electrophotographic photoreceptor having a two-layer photosensitive layer was obtained. The photoreceptor thus obtained was transferred to a commercially available electrophotographic copying machine (
-6K using EP-470Z; manufactured by Minolta Camera Co., Ltd.
The initial surface potential Vo (V) was corona charged with V, and the exposure amount E1/2 (l
ux ·sec) and the decay rate DDR1 (%) of the initial potential when left in the dark for 1 second.
【００２４】（実施例２〜４）実施例１と同様の方法で
同一の構成のもの、但し実施例１で用いたアミノビフェ
ニル化合物〔化６の（１）〕の代りにアミノビフェニル
化合物，化６の（２），（３）及び化７の（９）を各々
用いる感光体を作製した。こうして得られた感光体につ
いて、実施例１と同様の方法でＶｏ 、Ｅ１／２ 、Ｄ
ＤＲ１ を測定した。(Examples 2 to 4) Same method and same composition as in Example 1, except that the aminobiphenyl compound [Chemical formula 6 (1)] used in Example 1 was replaced with an aminobiphenyl compound, Formula 6. Photoreceptors were prepared using each of (2) and (3) in Chemical Formula 6 and (9) in Chemical Formula 7. Regarding the photoreceptor thus obtained, Vo, E1/2, D
DR1 was measured.
【００２５】（実施例５）下記一般式〔Ｂ〕〔化１６〕
で表されるビスアゾ化合物(Example 5) The following general formula [B] [Chemical formula 16]
bisazo compound represented by
【化１６】
０．４５部、ポリスチレン樹脂（分子量４００００）０
．４５部をシクロヘキサノン５０部とともにサンドグラ
インダーにより分散させた。得られたビスアゾ化合物の
分散液を厚さ１００μｍのアルミ化マイラー上にフィル
ムアプリケーターを用いて、乾燥膜厚が０．３ｇ／ｍ２
となる様に塗布した後乾燥させた。このようにして得
られた電荷発生層の上にアミノビフェニル化合物〔化７
の（１０）〕７０部およびポリアリレート樹脂（Ｕ−１
００；ユニチカ社製）７０部を１，４ジオキサン４００
部に溶解した溶液を乾燥膜厚が１６μｍになるように塗
布し、電荷発生層を形成した。この様にして、２層から
なる感光層を有する電子写真感光体を作製した。[Chemical formula 16] 0.45 parts, polystyrene resin (molecular weight 40,000) 0
．． 45 parts were dispersed with 50 parts of cyclohexanone in a sand grinder. The resulting bisazo compound dispersion was applied onto a 100 μm thick aluminized Mylar using a film applicator to give a dry film thickness of 0.3 g/m2.
It was applied and dried. An aminobiphenyl compound [Chemical formula 7] is placed on the charge generation layer thus obtained.
(10)] 70 parts and polyarylate resin (U-1
00; manufactured by Unitika) 70 parts to 400 parts of 1,4 dioxane
A charge generation layer was formed by applying the solution dissolved in the sample to a dry film thickness of 16 μm. In this manner, an electrophotographic photoreceptor having a two-layer photosensitive layer was produced.
【００２６】（実施例６〜８）実施例５と同様の方法で
同一の構成のもの、但し実施例５で用いたアミノビフェ
ニル化合物〔化７の（１０）〕の代りにアミノビフェニ
ル化合物化７の（１１），化８の（１２），（１３）を
各々用いる感光体を作製した。こうして得られた感光体
について、実施例１と同様の方法でＶｏ 、Ｅ１／２
、ＤＤＲ１ を測定した。(Examples 6 to 8) Same method and same composition as in Example 5, except that aminobiphenyl compound [Chemical formula 7 (10)] used in Example 5 was replaced with aminobiphenyl compound Compound 7. Photoreceptors were prepared using (11), chemical formula 8 (12), and (13), respectively. Regarding the photoreceptor thus obtained, Vo and E1/2 were obtained in the same manner as in Example 1.
, DDR1 was measured.
【００２７】（実施例９）銅フタロシアニン５０部とテ
トラニトロ銅フタロシアニン０．２部を９８％濃硫酸５
００部に充分撹拌しながら溶解させ、これを水５０００
部にあけ、銅フタロシアニンとテトラニトロ銅フタロシ
アニンの光導電性材料組成物を析出させた後、濾過、水
洗し、減圧下１２０℃で乾燥した。こうして得られた光
導電性組成物１０部を熱硬化性アクリル樹脂（アクリデ
ィクＡ４０５；大日本インク社製）２２．５部、メラミ
ン樹脂（スーパーベッカミンＪ８２０；大日本インク社
製）７．５部、前述したアミノビフェニル化合物〔化８
の（１４）〕１５部を、メチルエチルケトンとキシレン
を同量に混合した混合溶剤１００部とともにボールミル
ポットに入れて４８時間分散し感光性塗液を調整し、こ
の塗液をアルミニウム基体上に塗布、乾燥して厚さ約１
５μｍの感光層を形成させ感光体を作製した。こうして
得られた感光体について、実施例１と同様の方法、但し
コロナ帯電を＋６ＫＶで行なってＶｏ 、Ｅ１／２ 、
ＤＤＲ１ を測定した。(Example 9) 50 parts of copper phthalocyanine and 0.2 parts of tetranitrocopper phthalocyanine were added to 5 parts of 98% concentrated sulfuric acid.
00 parts with sufficient stirring, and add 5000 parts of water.
After depositing a photoconductive material composition of copper phthalocyanine and tetranitrocopper phthalocyanine, it was filtered, washed with water, and dried at 120° C. under reduced pressure. 10 parts of the photoconductive composition thus obtained were mixed with 22.5 parts of a thermosetting acrylic resin (Acridik A405; manufactured by Dainippon Ink Co., Ltd.) and 7.5 parts of a melamine resin (Super Beckamine J820; manufactured by Dainippon Ink Co., Ltd.). , the above-mentioned aminobiphenyl compound [Chemical formula 8
(14)] was placed in a ball mill pot with 100 parts of a mixed solvent of equal amounts of methyl ethyl ketone and xylene and dispersed for 48 hours to prepare a photosensitive coating liquid, and this coating liquid was applied onto an aluminum substrate. Approximately 1 thick when dry
A photoreceptor was prepared by forming a 5 μm photosensitive layer. The thus obtained photoreceptor was charged in the same manner as in Example 1, except that corona charging was performed at +6 KV to obtain Vo, E1/2,
DDR1 was measured.
【００２８】（実施例１０〜１２）実施例９と同様の方
法で同一の構成のもの、但し実施例９で用いたアミノビ
フェニル化合物〔化８の（１４）〕の代りにアミノビフ
ェニル化合物，化８の（１５），（１６）及び化９の（
１７），を各々用いる感光体を作製した。こうして得ら
れた感光体について、実施例９と同様の方法でＶｏ 、
Ｅ１／２ 、ＤＤＲ１ を測定した。(Examples 10 to 12) The same method and composition as in Example 9 were carried out, except that the aminobiphenyl compound [(14) of Chemical Formula 8] used in Example 9 was replaced with an aminobiphenyl compound, Chemical Formula 8. 8 (15), (16) and Chemical 9 (
17), photoreceptors were prepared using each of the following methods. Regarding the thus obtained photoreceptor, Vo,
E1/2 and DDR1 were measured.
【００２９】（比較例１〜４）実施例９と同様の方法で
同一の構成のもの、但し実施例９で用いたアミノビフェ
ニル化合物〔化８の（１４）〕の代りに下記化合物化１
７の〔Ｃ〕、〔Ｄ〕、〔Ｅ〕、〔Ｆ〕、を各々用いる以
外は実施例９と全く同様にして感光体を作製した。(Comparative Examples 1 to 4) Same composition as in Example 9, except that the aminobiphenyl compound [Chemical formula 8 (14)] used in Example 9 was replaced with the following compound Formula 1.
A photoreceptor was produced in exactly the same manner as in Example 9 except that [C], [D], [E], and [F] of No. 7 were used respectively.
【化１７】
こうして得られた感光体について、実施例９と同様の方
法でＶｏ 、Ｅ１／２ 、ＤＤＲ１ を測定した。embedded image Vo , E1/2 and DDR1 of the thus obtained photoreceptor were measured in the same manner as in Example 9.
【００３０】（比較例５〜８）実施例９と同様の方法で
同一の構成のもの、但し実施例９で用いたアミノビフェ
ニル化合物〔化８の（１４）〕の代りに下記アミノビフ
ェニル化合物，化１８の〔Ｇ〕、〔Ｈ〕、〔Ｉ〕、〔Ｊ
〕を各々用いる以外は実施例９と全く同様にして感光体
を作製した。(Comparative Examples 5 to 8) The same method and composition as in Example 9 were carried out, except that the following aminobiphenyl compound ((14) in Chemical Formula 8) was used in place of the aminobiphenyl compound used in Example 9. Chemical formula 18 [G], [H], [I], [J
] A photoreceptor was produced in exactly the same manner as in Example 9 except that each of the following was used.
【化１８】
こうして得られた感光体について、実施例９と同様の方
法でＶｏ 、Ｅ１／２ 、ＤＤＲ１ を測定した。実施
例１〜１２、比較例１〜８で得られた感光体のＶｏ 、
Ｅ１／２ 、ＤＤＲ１ の測定結果を表１にまとめて示
す。embedded image Vo , E1/2 and DDR1 of the thus obtained photoreceptor were measured in the same manner as in Example 9. Vo of the photoreceptors obtained in Examples 1 to 12 and Comparative Examples 1 to 8,
The measurement results of E1/2 and DDR1 are summarized in Table 1.
【００３１】[0031]
【表１】
表１からわかるように、本発明の感光体は積層型でも単
層型でも電荷保持能が充分あり、暗減衰率も感光体とし
ては充分使用可能な程度に小さく、また、感度において
も優れている。更に、市販の電子写真複写機（ＥＰ−３
５０Ｚ；ミノルタカメラ社製）による正帯電時の繰り返
し実写テストを実施例９の感光体において行なったが、
１０００枚のコピーを行なっても、初期、最終画像にお
いて階調性が優れ、感度変化が無く、鮮明な画像が得ら
れ、本発明の感光体は繰り返し特性も安定していること
がわかる。[Table 1] As can be seen from Table 1, the photoreceptor of the present invention has sufficient charge retention ability whether it is a laminated type or a single layer type, the dark decay rate is small enough to be used as a photoreceptor, and the sensitivity is It is also excellent in Furthermore, a commercially available electrophotographic copying machine (EP-3
50Z (manufactured by Minolta Camera Co., Ltd.) was used for the photoconductor of Example 9, and a repeated live-photograph test was conducted during positive charging.
It can be seen that even after 1000 copies were made, clear images with excellent gradation and no change in sensitivity were obtained in the initial and final images, and the photoreceptor of the present invention had stable repeatability.
【００３２】[0032]
【発明の効果】本発明は感光体に有用な光導電性化合物
を提供した。本発明の光導電性化合物は、特に電荷輸送
材料として有用である。本発明のアミノビフェニル化合
物は結着剤に対して高い相溶性を持ち、本発明のアミノ
ビフェニル化合物を有する感光体は、感度、電荷輸送性
、初期表面電位、暗減衰率の感光体特性に優れ、繰り返
し使用に対する光疲労も少ない。The present invention provides a photoconductive compound useful for photoreceptors. The photoconductive compounds of the present invention are particularly useful as charge transport materials. The aminobiphenyl compound of the present invention has high compatibility with a binder, and the photoreceptor containing the aminobiphenyl compound of the present invention has excellent photoreceptor properties such as sensitivity, charge transport property, initial surface potential, and dark decay rate. Also, there is little optical fatigue due to repeated use.
【図１】本発明に係わる導電性支持体上に感光層を積層
してなる分散型感光体の構造の模式図FIG. 1 is a schematic diagram of the structure of a dispersed photoreceptor in which a photosensitive layer is laminated on a conductive support according to the present invention.
【図２】本発明に係わる導電性支持体上に電荷発生層と
電荷輸送層を積層してなる機能分離型感光体の構造の模
式図FIG. 2 is a schematic diagram of the structure of a functionally separated photoreceptor in which a charge generation layer and a charge transport layer are laminated on a conductive support according to the present invention.
【図３】他の態様の同上模式図[Figure 3] Schematic diagram of another embodiment of the same as above.
【図４】本発明に係わる導電性支持体上に感光層を積層
してなる分散型感光体の他の態様の構造の模式図FIG. 4 is a schematic diagram of the structure of another embodiment of the dispersion type photoreceptor in which a photosensitive layer is laminated on a conductive support according to the present invention.
【図５
】更に他の態様の同上模式図[Figure 5
】Schematic diagram of still another aspect of the same as above.
１ 導電性支持体 ２ 電荷輸送材料 ３ 光導電性材料 ４ 感光層 ５ 電荷輸送層 ６ 電荷発生層 ７ 表面保護層 ８ 中間層 1 Conductive support 2 Charge transport material 3 Photoconductive material 4 Photosensitive layer 5 Charge transport layer 6 Charge generation layer 7 Surface protective layer 8 Middle class
Claims (1)
（化１）で示されるアミノビフェニル化合物を含有す
る感光層を有する感光体 【化１】 〔式中、Ｒ１ ，Ｒ２ はそれぞれ独立して水素原子、
アルキル基、アルコキシ基またはハロゲン原子を示す；
Ｒ３ ，Ｒ４ ，Ｒ５ ，Ｒ６ は、それぞれ独立して
水素原子、置換基を有していてもよいアルキル基、ジア
ルキルアミノ基、アルコキシ基、チオアルコキシ基、ア
リールオキシ基、またはハロゲン原子を示す〕。Claim 1: On a conductive support, the following general formula [I]
Photoreceptor having a photosensitive layer containing an aminobiphenyl compound represented by (Chemical formula 1) [Chemical formula 1] [In the formula, R1 and R2 are each independently a hydrogen atom,
Indicates an alkyl group, an alkoxy group or a halogen atom;
R3, R4, R5 and R6 each independently represent a hydrogen atom, an alkyl group which may have a substituent, a dialkylamino group, an alkoxy group, a thioalkoxy group, an aryloxy group, or a halogen atom].
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP41781790A JP2957286B2 (en) | 1990-12-26 | 1990-12-26 | Photoconductor |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP41781790A JP2957286B2 (en) | 1990-12-26 | 1990-12-26 | Photoconductor |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH04225363A true JPH04225363A (en) | 1992-08-14 |
| JP2957286B2 JP2957286B2 (en) | 1999-10-04 |
Family
ID=18525854
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP41781790A Expired - Lifetime JP2957286B2 (en) | 1990-12-26 | 1990-12-26 | Photoconductor |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2957286B2 (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009282147A (en) * | 2008-05-20 | 2009-12-03 | Sharp Corp | Stacked electrophotographic photoreceptor and image forming apparatus including the same |
| US8399605B2 (en) | 2005-12-22 | 2013-03-19 | Cambridge Display Technology Limited | Arylamine polymer |
| US8716697B2 (en) | 2004-02-20 | 2014-05-06 | E I Du Pont De Nemours And Company | Electronic devices made with crosslinkable compounds and copolymers |
| JP2020040962A (en) * | 2014-03-27 | 2020-03-19 | 日産化学株式会社 | N,n,n',n'-tetraphenyl benzidine compound |
| US10868254B2 (en) * | 2012-10-17 | 2020-12-15 | Novaled Gmbh | Phosphorescent OLED and hole transporting materials for phosphorescent OLEDS |
-
1990
- 1990-12-26 JP JP41781790A patent/JP2957286B2/en not_active Expired - Lifetime
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8716697B2 (en) | 2004-02-20 | 2014-05-06 | E I Du Pont De Nemours And Company | Electronic devices made with crosslinkable compounds and copolymers |
| US8399605B2 (en) | 2005-12-22 | 2013-03-19 | Cambridge Display Technology Limited | Arylamine polymer |
| JP2009282147A (en) * | 2008-05-20 | 2009-12-03 | Sharp Corp | Stacked electrophotographic photoreceptor and image forming apparatus including the same |
| US20090317136A1 (en) * | 2008-05-20 | 2009-12-24 | Sharp Kabushiki Kaisha | Multilayered electrophotographic photoreceptor and image formation apparatus provided with the same |
| US10868254B2 (en) * | 2012-10-17 | 2020-12-15 | Novaled Gmbh | Phosphorescent OLED and hole transporting materials for phosphorescent OLEDS |
| JP2020040962A (en) * | 2014-03-27 | 2020-03-19 | 日産化学株式会社 | N,n,n',n'-tetraphenyl benzidine compound |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2957286B2 (en) | 1999-10-04 |
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