JPH0561220A - Electrophotographic sensitive body - Google Patents
Electrophotographic sensitive bodyInfo
- Publication number
- JPH0561220A JPH0561220A JP22005291A JP22005291A JPH0561220A JP H0561220 A JPH0561220 A JP H0561220A JP 22005291 A JP22005291 A JP 22005291A JP 22005291 A JP22005291 A JP 22005291A JP H0561220 A JPH0561220 A JP H0561220A
- Authority
- JP
- Japan
- Prior art keywords
- layer
- charge
- compound
- resin
- photoconductor
- 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
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
- 239000000126 substance Substances 0.000 claims description 42
- 108091008695 photoreceptors Proteins 0.000 claims description 26
- -1 chalcone compound Chemical class 0.000 claims description 15
- DQFBYFPFKXHELB-UHFFFAOYSA-N Chalcone Natural products C=1C=CC=CC=1C(=O)C=CC1=CC=CC=C1 DQFBYFPFKXHELB-UHFFFAOYSA-N 0.000 claims description 6
- 235000005513 chalcones Nutrition 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 239000000463 material Substances 0.000 abstract description 15
- 230000035945 sensitivity Effects 0.000 abstract description 7
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 239000000758 substrate Substances 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 73
- 150000001875 compounds Chemical class 0.000 description 30
- 229920005989 resin Polymers 0.000 description 27
- 239000011347 resin Substances 0.000 description 27
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- 239000000975 dye Substances 0.000 description 16
- 239000011230 binding agent Substances 0.000 description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- 239000002245 particle Substances 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- 239000011241 protective layer Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Natural products CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000002344 surface layer Substances 0.000 description 5
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 230000009471 action Effects 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000004419 Panlite Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 3
- 230000006870 function Effects 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
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 3
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 3
- 229910052711 selenium Inorganic materials 0.000 description 3
- 239000011669 selenium Substances 0.000 description 3
- 239000007787 solid 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
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- GNKZMNRKLCTJAY-UHFFFAOYSA-N 4'-Methylacetophenone Chemical compound CC(=O)C1=CC=C(C)C=C1 GNKZMNRKLCTJAY-UHFFFAOYSA-N 0.000 description 2
- NTPLXRHDUXRPNE-UHFFFAOYSA-N 4-methoxyacetophenone Chemical compound COC1=CC=C(C(C)=O)C=C1 NTPLXRHDUXRPNE-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229910001215 Te alloy Inorganic materials 0.000 description 2
- 229920002433 Vinyl chloride-vinyl acetate copolymer Polymers 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052980 cadmium sulfide Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 229920006026 co-polymeric resin Polymers 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 230000036541 health Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- LAQFLZHBVPULPL-UHFFFAOYSA-N methyl(phenyl)silicon Chemical compound C[Si]C1=CC=CC=C1 LAQFLZHBVPULPL-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- SJHHDDDGXWOYOE-UHFFFAOYSA-N oxytitamium phthalocyanine Chemical compound [Ti+2]=O.C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 SJHHDDDGXWOYOE-UHFFFAOYSA-N 0.000 description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
- 229920006267 polyester film 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
- 238000011160 research Methods 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- BUZYGTVTZYSBCU-UHFFFAOYSA-N 1-(4-chlorophenyl)ethanone Chemical compound CC(=O)C1=CC=C(Cl)C=C1 BUZYGTVTZYSBCU-UHFFFAOYSA-N 0.000 description 1
- ZDVRPKUWYQVVDX-UHFFFAOYSA-N 2-(trifluoromethyl)benzaldehyde Chemical compound FC(F)(F)C1=CC=CC=C1C=O ZDVRPKUWYQVVDX-UHFFFAOYSA-N 0.000 description 1
- JTWHVBNYYWFXSI-UHFFFAOYSA-N 2-nitro-1-phenylethanone Chemical compound [O-][N+](=O)CC(=O)C1=CC=CC=C1 JTWHVBNYYWFXSI-UHFFFAOYSA-N 0.000 description 1
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 1
- WUPHOULIZUERAE-UHFFFAOYSA-N 3-(oxolan-2-yl)propanoic acid Chemical compound OC(=O)CCC1CCCO1 WUPHOULIZUERAE-UHFFFAOYSA-N 0.000 description 1
- NLPHXWGWBKZSJC-UHFFFAOYSA-N 4-acetylbenzonitrile Chemical compound CC(=O)C1=CC=C(C#N)C=C1 NLPHXWGWBKZSJC-UHFFFAOYSA-N 0.000 description 1
- ARIREUPIXAKDAY-UHFFFAOYSA-N 4-butylbenzaldehyde Chemical compound CCCCC1=CC=C(C=O)C=C1 ARIREUPIXAKDAY-UHFFFAOYSA-N 0.000 description 1
- AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 1
- WZWIQYMTQZCSKI-UHFFFAOYSA-N 4-cyanobenzaldehyde Chemical compound O=CC1=CC=C(C#N)C=C1 WZWIQYMTQZCSKI-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
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- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
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- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
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- 239000004677 Nylon Substances 0.000 description 1
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- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene 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
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
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- 125000004429 atom Chemical group 0.000 description 1
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 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
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- 125000001309 chloro group Chemical group Cl* 0.000 description 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
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- 150000003839 salts Chemical class 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- QXKXDIKCIPXUPL-UHFFFAOYSA-N sulfanylidenemercury Chemical compound [Hg]=S QXKXDIKCIPXUPL-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000001016 thiazine dye Substances 0.000 description 1
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 239000001003 triarylmethane dye Substances 0.000 description 1
- 229960002415 trichloroethylene Drugs 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000001018 xanthene dye Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Photoreceptors In Electrophotography (AREA)
Abstract
Description
【0001】[0001]
【産業上の利用分野】本発明は電子写真感光体、特に、
電荷輸送材料としてカルコン系化合物を含有する電子写
真感光体に関する。FIELD OF THE INVENTION The present invention relates to electrophotographic photoreceptors,
The present invention relates to an electrophotographic photoreceptor containing a chalcone compound as a charge transport material.
【0002】[0002]
【従来の技術】従来、電子写真感光体の感光層として、
セレン、セレン−テルル合金、酸化亜鉛などの無機光導
電性物質が広く用いられてきたが、近年、有機光導電性
物質を用いた電子写真感光体に関する研究が進み、その
一部は実用化されている。ここで、実用化に至った感光
体のほとんどは、電荷発生層と電荷輸送層に機能を分離
した感光層からなる積層型電子写真感光体であり、これ
により、無機光導電性物質からなる感光体と比較して劣
っていた感度及び感光体寿命の点で改善され、低コスト
で、安全性や多様性など有機光導電性物質の長所を生か
した電子写真感光体の設計が活発に行なわれるようにな
った。2. Description of the Related Art Conventionally, as a photosensitive layer of an electrophotographic photoreceptor,
Inorganic photoconductive substances such as selenium, selenium-tellurium alloy, and zinc oxide have been widely used, but in recent years, research on electrophotographic photoreceptors using organic photoconductive substances has progressed, and some of them have been put to practical use. ing. Here, most of the photoconductors that have been put to practical use are laminated electrophotographic photoconductors that include a photogenerating layer having a charge-generating layer and a charge-transporting layer that have different functions. The electrophotographic photoconductor is actively designed, which is improved in terms of sensitivity and photoconductor life, which are inferior to those of the human body, and is low cost, and takes advantage of the advantages of organic photoconductive materials such as safety and versatility. It became so.
【0003】この種の積層型電子写真感光体は、一般に
は、導電性支持体上に、顔料、染料などの電荷発生物質
からなる電荷発生層、ヒドラゾン、ピラゾリンなど電荷
輸送物質からなる電荷輸送層を順に形成したもので、電
子供与性である電荷輸送物質の性質上、正孔移動型とな
り、感光体表面に負帯電したとき感度を有する。ところ
が、負帯電では、帯電時に用いるコロナ放電が正帯電に
比べて不安定であり、正帯電時の10倍程度のオゾン、
窒素酸化物などを発生し、感光体表面に吸着などの物理
的劣化や化学的劣化を引き起こしやすく、さらに、環境
を悪くすると言う問題がある。さらに他の問題は、負帯
電用感光体の現像には正極性のトナーが必要となるが正
極性のトナーは強磁性体キャリア粒子に体する摩擦帯電
系列から見て製造が困難であり、2成分高抵抗磁気ブラ
シ現像方式においては、負帯電トナー/現像剤の方が安
定であり、選択と使用条件の自由度も大きく、この点で
も正帯電型感光体に適用範囲は広く有利である。This type of laminated electrophotographic photoreceptor is generally a charge generating layer made of a charge generating substance such as a pigment or a dye, and a charge transporting layer made of a charge transporting substance such as hydrazone or pyrazoline on a conductive support. Are sequentially formed. Due to the nature of the electron-donating charge transport material, they are of the hole transfer type and have sensitivity when negatively charged on the surface of the photoreceptor. However, with negative charging, the corona discharge used during charging is more unstable than with positive charging, and ozone is about 10 times as much as during positive charging.
There is a problem that nitrogen oxides and the like are generated, and physical deterioration such as adsorption on the surface of the photoconductor or chemical deterioration is easily caused, and further the environment is deteriorated. Still another problem is that the development of the negative charging photoreceptor requires a toner having a positive polarity, but the toner having a positive polarity is difficult to manufacture in view of the triboelectrification series in which the carrier particles of ferromagnetic material are contained. In the component high-resistance magnetic brush developing method, the negatively charged toner / developer is more stable, and the degree of freedom in selection and use conditions is large, and in this respect, the range of application to the positively charged type photoreceptor is wide and advantageous.
【0004】そこで、有機光導電性物質を用いる感光体
を正帯電で使用することが提案されている。例えば、電
荷発生層上に電荷輸送層を積層して感光体を形成する
際、前記電荷輸送層に電子輸送能の大きい、例えば2,
4,7−トリニトロ−9−フルオレノン等が使用されて
いるが、その物質は発癌性があり、労働衛生上極めて不
適当である等の問題がある。Therefore, it has been proposed to use a photoconductor using an organic photoconductive material with a positive charge. For example, when a charge transport layer is laminated on the charge generation layer to form a photoreceptor, the charge transport layer has a large electron transport ability, for example, 2,
Although 4,7-trinitro-9-fluorenone and the like are used, there is a problem that the substance has carcinogenicity and is extremely unsuitable for occupational health.
【0005】さらに正帯電感光体として、米国特許3,
615,414号には、チアピリリウム塩(電荷発生物
質)をポリカーボネート(バインダ樹脂)と共晶錯体を
形成するように含有されたものが示されている。しかし
この公知の感光体では、メモリ現象が大きく、ゴースト
も発生し易いという欠点がある。Further, as a positively charged photoreceptor, US Pat.
No. 615,414 discloses that thiapyrylium salt (charge generating substance) is contained so as to form a eutectic complex with polycarbonate (binder resin). However, this known photoconductor has a drawback that a memory phenomenon is large and a ghost is easily generated.
【0006】そこで光照射時、正孔及び電子を発生する
電荷発生物質を含有する電荷発生層を上層(表面層)と
し、正孔輸送能を有する電荷輸送物質を含む電荷輸送層
を下層とする積層構成の感光層を有する感光体を正帯電
用として使用可能と考えられる。しかしながら、前記正
帯電用感光体は電荷発生物質を含む層が表面層として形
成されるため、光照射時特に紫外線等の短波長光照射、
コロナ放電、湿度、機械的摩擦等の外部作用に脆弱な電
荷発生物質が前記表面層近傍に存在することになり、感
光体の保存中及び像形成過程で電子写真性能が劣化し、
画質が低下するようになる。Therefore, the charge generation layer containing a charge generation substance that generates holes and electrons at the time of light irradiation is used as an upper layer (surface layer), and the charge transport layer containing a charge transport substance having a hole transport ability is used as a lower layer. It is considered that a photoreceptor having a laminated photosensitive layer can be used for positive charging. However, since the layer containing the charge generating substance is formed as the surface layer in the positive charging photoreceptor, at the time of light irradiation, short-wavelength light irradiation such as ultraviolet light irradiation,
Corona discharge, humidity, a charge generating substance vulnerable to external action such as mechanical friction will be present in the vicinity of the surface layer, electrophotographic performance is deteriorated during storage of the photoconductor and during image formation,
The image quality will deteriorate.
【0007】従来の電荷輸送層を表面層とする負帯電用
感光体においては、前記各種の外部作用の影響は極めて
少なく、むしろ、前記電荷輸送層が下層の電荷発生層を
保護する作用を有している。In the conventional negative charging photoreceptor having the charge transport layer as the surface layer, the influence of the various external actions is extremely small, and rather the charge transport layer has a function of protecting the lower charge generating layer. is doing.
【0008】そこで、例えば絶縁性かつ透明な樹脂から
なる薄い保護層を設け、前記電荷発生物質を含む層を外
部作用から保護することが考えられるが、光照射時発生
する電荷がその保護層でブロッキングされて光照射効果
が失われてくるし、また表面層となる保護層の膜厚が大
きい場合には感度低下を招くことになる。Therefore, for example, a thin protective layer made of an insulating and transparent resin may be provided to protect the layer containing the charge generating substance from an external action. However, the charge generated during light irradiation is the protective layer. The light irradiation effect is lost due to blocking, and the sensitivity is lowered when the thickness of the protective layer serving as the surface layer is large.
【0009】このように正帯電用感光体を得るための試
みが種々行なわれているが、いずれも、光感度、メモリ
現象または労働衛生等の点で改善すべき多くの問題点が
ある。Although various attempts have been made to obtain a photoconductor for positive charging as described above, all of them have many problems to be solved in terms of photosensitivity, memory phenomenon, occupational health and the like.
【0010】[0010]
【発明が解決しようとする課題】本発明は、導電性支持
体上に電荷発生物質及び電荷輸送物質を含有し、高感度
で耐久性のよい電子写真感光体を提供しようとするもの
である。DISCLOSURE OF THE INVENTION The present invention is intended to provide an electrophotographic photoreceptor containing a charge generating substance and a charge transporting substance on a conductive support and having high sensitivity and durability.
【0011】[0011]
【課題を解決するための手段】本発明者らは、上記の課
題を解決すべく従来より研究を重ねてきた結果、特定の
一群の化合物を見出すにいたり、本発明を完成した。Means for Solving the Problems The inventors of the present invention have conducted extensive research to solve the above-mentioned problems and, as a result, found a specific group of compounds and completed the present invention.
【0012】すなわち、本発明の構成は特許請求の範囲
に記載のとおりの電子写真感光体である。That is, the constitution of the present invention is an electrophotographic photoreceptor as set forth in the claims.
【0013】次に、本明細書の請求項2に記載の一般式
Iの化合物について具体的に説明する。Next, the compound of the general formula I described in claim 2 of the present specification will be specifically explained.
【0014】本発明の前記一般式I中、R1及びR2にお
けるフェニル基及びナフチル基の置換基としては、アル
キル基、例えばメチル基、エチル基、プロピル基、ブチ
ル基、t−ブチル基などが挙げられ、アルコキシ基、例
えばメトキシ基、エトキシ基などが挙げられ、ハロゲン
原子、例えばフッ素原子、塩素原子、臭素原子などが挙
げられ、ハロゲン化アルキル基としてトリフルオロメチ
ル基などが挙げられ、アルコキシカルボニル基としてメ
トキシカルボニル基、エトキシカルボニル基などが挙げ
られ、さらにシアノ基、ニトロ基などが挙げられ、複素
芳香環としてはピリジン環、キノリン環などを挙げるこ
とができる。In the general formula I of the present invention, the substituents of the phenyl group and the naphthyl group in R 1 and R 2 are alkyl groups such as methyl group, ethyl group, propyl group, butyl group and t-butyl group. Alkoxy group, for example, methoxy group, ethoxy group and the like, halogen atom, for example, fluorine atom, chlorine atom, bromine atom and the like, trifluoromethyl group and the like as the halogenated alkyl group, alkoxy Examples of the carbonyl group include a methoxycarbonyl group and an ethoxycarbonyl group, further examples include a cyano group and a nitro group, and examples of the heteroaromatic ring include a pyridine ring and a quinoline ring.
【0015】本発明の一般式Iのカルコン系化合物の具
体例を、下記一般式Iとの関連で表1に示すが、これら
に限定されるものではない。Specific examples of the chalcone compound of the general formula I of the present invention are shown in Table 1 in relation to the following general formula I, but not limited thereto.
【0016】 [0016]
【0017】[0017]
【表1】 [Table 1]
【0018】[0018]
【表2】 [Table 2]
【0019】[0019]
【表3】 [Table 3]
【0020】[0020]
【表4】 [Table 4]
【0021】[0021]
【表5】 [Table 5]
【0022】[0022]
【表6】 [Table 6]
【0023】[0023]
【表7】 [Table 7]
【0024】[0024]
【表8】 [Table 8]
【0025】[0025]
【表9】 [Table 9]
【0026】これら一般式Iの化合物は一般に下記アセ
フェノン系化合物と下記アルデヒド類とを塩基性触媒下
で反応することによって得られる。These compounds of general formula I are generally obtained by reacting the following acephenone compounds with the following aldehydes under a basic catalyst.
【0027】 (式中、R1は置換または非置換のフェニル基、置換ま
たは非置換のナフチル基、あるいは複素芳香環を示
す。) R2−CHO (式中、R2は置換または非置換のフェニル基、置換ま
たは非置換のナフチル基、あるいは複素芳香環を示
す。) アセトフェノン系化合物としては例えばアセトフェノ
ン、P−メチルアセトフェノン、P−メトキシアセトフ
ェノン、P−クロロアセトフェノン、エチルアセチルベ
ンゾエート、P−シアノアセトフェノン、P−ニトロア
セトフェノンなどが挙げられ、アルデヒド類としては、
ベンズアルデヒド、P−クロロベンズアルデヒド、P−
トリフルオロメチルベンズアルテヒド、P−ナフトアル
デヒド、P−シアノベンズアルデヒド、P−ブチルベン
ズアルデヒドなどが挙げられる。[0027] (In the formula, R 1 represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a heteroaromatic ring.) R 2 —CHO (wherein R 2 is a substituted or unsubstituted phenyl group, A substituted or unsubstituted naphthyl group or a heteroaromatic ring is shown.) Examples of the acetophenone compound include acetophenone, P-methylacetophenone, P-methoxyacetophenone, P-chloroacetophenone, ethylacetylbenzoate, P-cyanoacetophenone, P- Examples of aldehydes include nitroacetophenone.
Benzaldehyde, P-chlorobenzaldehyde, P-
Examples thereof include trifluoromethylbenzaldehyde, P-naphthaldehyde, P-cyanobenzaldehyde, P-butylbenzaldehyde and the like.
【0028】また、塩基性触媒としては、例えば炭酸ナ
トリウム、炭酸カリウム、水酸化ナトリウム、水酸化カ
リウム、酢酸ナトリウム、ピリジン、ピペリジンなどが
挙げられる。Examples of the basic catalyst include sodium carbonate, potassium carbonate, sodium hydroxide, potassium hydroxide, sodium acetate, pyridine, piperidine and the like.
【0029】さらに反応溶媒としては、エタノール、
N,N−ジメチルホルムアミド、テトラヒドロフラン、
ジオキサンなどが挙げられる。反応温度は室温からそれ
ぞれの溶媒の還流温度までが好ましい。Further, as a reaction solvent, ethanol,
N, N-dimethylformamide, tetrahydrofuran,
Examples include dioxane. The reaction temperature is preferably from room temperature to the reflux temperature of each solvent.
【0030】合成例1 水酸化ナトリウム4.4g(110mmol)をエタノ
ール20g/水39.2gの混合溶媒に溶解し、アセト
フェノン10.32g(86mmol)を氷冷しながら
投入し、さらにベンズアルデヒド9.12g(86mm
ol)を投入(ただし、この時の温度は15〜36℃と
する)し、撹拌反応させる.そのまま反応容器を冷却し
黄色固体を析出させる。その後、濾取し、洗浄、n−ヘ
キサンで再結晶精製を行なう。Synthesis Example 1 4.4 g (110 mmol) of sodium hydroxide was dissolved in a mixed solvent of 20 g of ethanol / 39.2 g of water, and 10.32 g (86 mmol) of acetophenone was added while cooling with ice, and further benzaldehyde 9.12 g. (86 mm
ol) (however, the temperature at this time is 15 to 36 ° C.) and the reaction is carried out with stirring. The reaction vessel is cooled as it is to precipitate a yellow solid. Then, it is collected by filtration, washed and purified by recrystallization with n-hexane.
【0031】得られた固体は収量10.8g(収率6
0.4%)の黄色固体であった。なお、融点は57.5
〜58℃であった。The obtained solid had a yield of 10.8 g (yield 6
0.4%) of a yellow solid. The melting point is 57.5.
It was ~ 58 ° C.
【0032】以上のようにして得られた化合物の融点及
び元素分析結果を表2に示す。Table 2 shows the melting points and elemental analysis results of the compounds obtained as described above.
【0033】[0033]
【表10】 [Table 10]
【0034】次に本発明の感光体の構成を図面によって
説明する。感光体としては例えば図1に示すように支持
体1(導電性支持体又はシート上に導電層を設けたも
の)上に電荷発生物質と必要に応じてバインダー樹脂を
含有する層(電荷発生層)2を下層とし、電荷輸送物質
と必要に応じてバインダー樹脂を含有する層(電荷輸送
層)3を上層とする積層構成の感光体層4を設けたも
の、図2に示すように図1の感光体層4の上に保護層5
を設けたもの、及び図3に示すように支持体上に電荷発
生物質と電荷輸送物質と必要に応じてバインダー樹脂を
含有する単層構成の感光体層6を設けたもの等が挙げら
れるが、図3の単層構成の感光体層6の上層に保護層が
設けられてもよく、また支持体と感光体層の間に中間層
が設けられてもよい。Next, the structure of the photoconductor of the present invention will be described with reference to the drawings. As the photoconductor, for example, as shown in FIG. 1, a layer containing a charge generating substance and optionally a binder resin on a support 1 (a conductive support or a sheet on which a conductive layer is provided) (charge generating layer). 2) as a lower layer, and a photoreceptor layer 4 having a laminated structure in which a layer (charge transporting layer) 3 containing a charge transporting substance and optionally a binder resin as an upper layer is provided, and as shown in FIG. Protective layer 5 on photoreceptor layer 4
And the one in which a single-layer photosensitive layer 6 containing a charge-generating substance, a charge-transporting substance and, if necessary, a binder resin is provided on a support as shown in FIG. A protective layer may be provided on the photoreceptor layer 6 having the single-layer structure shown in FIG. 3, and an intermediate layer may be provided between the support and the photoreceptor layer.
【0035】本発明に使用する電荷発生物質としては、
可視光を吸収してフリー電荷を発生するものであれば、
無機物質及び有機物質のいずれをも用いることができ
る。例えば、無定形セレン、三方晶系セレン、セレン−
砒素合金、セレン−テルル合金、硫化カドミウム、セレ
ン化カドミウム、硫セレン化カドミウム、硫化水銀、酸
化鉛、硫化鉛、アモルファスシリコン等の無機物質、或
いはビスアゾ系色素、ポリアゾ系色素、トリアリールメ
タン系色素、チアジン系色素、オキサジン系色素、キサ
ンテン系色素、シアニン系色素、スチリル系色素、ピリ
リウム系色素、キナクリドン系色素、インジゴ系色素、
ペリレン系色素、多環キノン系色素、ビスベンズイミダ
ゾール系色素、インダンスロン系色素、スクアリリウム
系色素、アントラキノン系色素及びフタロシアニン系色
素等の有機物質が挙げられる。As the charge generating substance used in the present invention,
If it absorbs visible light and generates free charge,
Both inorganic and organic substances can be used. For example, amorphous selenium, trigonal selenium, selenium-
Inorganic substances such as arsenic alloys, selenium-tellurium alloys, cadmium sulfide, cadmium selenide, cadmium sulfide selenide, mercury sulfide, lead oxide, lead sulfide, and amorphous silicon, or bisazo dyes, polyazo dyes, triarylmethane dyes , Thiazine dye, oxazine dye, xanthene dye, cyanine dye, styryl dye, pyrylium dye, quinacridone dye, indigo dye,
Examples thereof include perylene dyes, polycyclic quinone dyes, bisbenzimidazole dyes, indanthrone dyes, squarylium dyes, anthraquinone dyes, and phthalocyanine dyes.
【0036】本発明において感光体層に使用可能なバイ
ンダー樹脂としては、例えばポリエチレン、ポリプロピ
レン、アクリル樹脂、メタクリル樹脂、塩化ビニル樹
脂、酢酸ビニル樹脂、エポキシ樹脂、ポリウレタン樹
脂、フェノール樹脂、ポリエステル樹脂、アルキッド樹
脂、ポリカーボネート樹脂、シリコン樹脂、メラミン樹
脂等の付加重合型樹脂、重付加型樹脂、重縮合型樹脂、
並びにこれらの樹脂の繰返し単位のうち2つ以上を含む
共重合樹脂、例えば塩化ビニル−酢酸ビニル共重合体、
塩化ビニル−酢酸ビニル−無水マレイン酸共重合体樹脂
等の絶縁性樹脂のほか、ポリ−N−ビニルカルバゾール
等の高分子有機半導体が挙げられる。Examples of the binder resin usable in the photosensitive layer in the present invention include polyethylene, polypropylene, acrylic resin, methacrylic resin, vinyl chloride resin, vinyl acetate resin, epoxy resin, polyurethane resin, phenol resin, polyester resin and alkyd. Resin, polycarbonate resin, silicone resin, addition polymerization type resin such as melamine resin, polyaddition type resin, polycondensation type resin,
And a copolymer resin containing two or more of the repeating units of these resins, for example, a vinyl chloride-vinyl acetate copolymer,
In addition to insulating resins such as vinyl chloride-vinyl acetate-maleic anhydride copolymer resins, polymer organic semiconductors such as poly-N-vinylcarbazole can be mentioned.
【0037】次に前記感光体層を支持する導電性支持体
としては、アルミニウム、ニッケルなどの金属板、金属
ドラムまたは金属箔、アルミニウム、酸化錫、酸化イン
ジウムなどを蒸着したプラスチックフィルム或いは導電
性物質を塗布した紙、プラスチックなどのフィルムまた
はドラムを使用することができる。As the conductive support for supporting the photosensitive layer, a metal plate of aluminum, nickel or the like, a metal drum or a metal foil, a plastic film deposited with aluminum, tin oxide, indium oxide or the like or a conductive substance is used. A coated paper, a film such as plastic, or a drum can be used.
【0038】本発明に係る感光体を電荷発生層と電荷輸
送層の積層構成で形成する場合、すなわち前述の図1及
び図2の場合、本発明の電荷輸送物質は、適当な溶媒に
単独もしくは適当なバインダ樹脂とともに溶解もしくは
分散せしめたものを塗布して乾燥させる方法により設け
る。電荷輸送層に用いられる溶媒としては、例えばN,
N−ジメチルホルムアミド、トルエン、キシレン、モノ
クロルベンゼン、1,2−ジクロルエタン、ジクロルメ
タン、1,1,1−トリクロルエタン、1,1,2−ト
リクロルエチレン、テトラヒドロフラン、メチルエチル
ケトン、シクロヘキサノン、酢酸エチル、酢酸ブチル等
を挙げることができる。この電荷輸送層中、電荷輸送物
質がバインダ樹脂に含有される割合は、バインダ樹脂1
00重量部に対して電荷輸送物質が20〜200重量部
とされる。When the photoreceptor according to the present invention is formed with a laminated structure of a charge generation layer and a charge transport layer, that is, in the case of FIGS. 1 and 2, the charge transport material of the present invention is used alone or in a suitable solvent. It is provided by a method in which a material dissolved or dispersed together with an appropriate binder resin is applied and dried. Examples of the solvent used for the charge transport layer include N,
N-dimethylformamide, toluene, xylene, monochlorobenzene, 1,2-dichloroethane, dichloromethane, 1,1,1-trichloroethane, 1,1,2-trichloroethylene, tetrahydrofuran, methylethylketone, cyclohexanone, ethyl acetate, butyl acetate, etc. Can be mentioned. In this charge transport layer, the ratio of the charge transport material contained in the binder resin is 1
The charge transport material is 20 to 200 parts by weight based on 00 parts by weight.
【0039】この時の電荷輸送層の膜厚は、好ましくは
5〜50μm、特に好ましくは5〜30μmである。At this time, the film thickness of the charge transport layer is preferably 5 to 50 μm, particularly preferably 5 to 30 μm.
【0040】電荷発生層は電荷発生物質を導電性支持体
上に真空蒸着するか、或いは適当な溶媒に単独もしくは
適当なバインダ樹脂と共に溶解もしくは分散せしめたも
のを塗布、乾燥して電荷輸送層と同様に形成することが
できる。The charge-generating layer is formed by vacuum-depositing the charge-generating substance on a conductive support, or by coating a suitable solvent alone or dissolved or dispersed with a suitable binder resin, and drying it to form a charge-transporting layer. It can be similarly formed.
【0041】上記電荷発生物質を分散せしめて電荷発生
層を形成する場合、その電荷発生物質は2μm以下、好
ましくは1μm以下の平均粒径の粉粒体とされるのが好
ましい。すなわち、粒径があまりに大きいと層中への分
散が悪くなると共に、粒子が表面に一部突出して表面の
平滑性が悪くなり、場合によっては粒子の突出部分で放
電が生じたり或いはそこにトナー粒子が付着してトナー
フィルミング現象が生じやすい。ただし、上記の粒径が
あまりに小さいと却って凝集しやすく、層の抵抗が上昇
したり、結晶欠陥が増えて感度及び繰返し特性が低下し
たり、或いは微細化する上で限界があるから、平均粒径
の下限を0.01μmとするのが好ましい。When the charge-generating layer is formed by dispersing the charge-generating substance, the charge-generating substance is preferably a powder having an average particle diameter of 2 μm or less, preferably 1 μm or less. That is, if the particle size is too large, the dispersion in the layer becomes poor, and the particles partially project on the surface and the surface smoothness deteriorates. Toner filming phenomenon tends to occur due to particles being attached. However, if the above particle size is too small, it tends to agglomerate, the resistance of the layer increases, the crystal defects increase and the sensitivity and repeatability deteriorate, or there is a limit on miniaturization, so the average particle The lower limit of the diameter is preferably 0.01 μm.
【0042】電荷発生層は、次の如き方法によって設け
ることができる。すなわち、電荷発生物質はボールミ
ル、ホモミキサー等によって分散媒中で微細粒子とし、
バインダ樹脂を加えて混合分散して得られる分散液を塗
布する方法である。この方法において超音波の作用下に
粒子を分散させると、均一分散が可能である。また電荷
発生層中、電荷発生物質がバインダ樹脂に含有される割
合は、バインダ樹脂100重量部に対して20〜200
重量部とされる。The charge generation layer can be provided by the following method. That is, the charge generating substance is made into fine particles in a dispersion medium by a ball mill, a homomixer, etc.,
This is a method of applying a binder resin and mixing and dispersing to obtain a dispersion liquid. In this method, if the particles are dispersed under the action of ultrasonic waves, uniform dispersion is possible. In the charge generation layer, the ratio of the charge generation substance contained in the binder resin is 20 to 200 with respect to 100 parts by weight of the binder resin.
It is considered to be part by weight.
【0043】以上のようにして形成される電荷発生層の
膜厚は、好ましくは0.1〜10μm、特に好ましくは
0.5〜5μmである。The thickness of the charge generation layer formed as described above is preferably 0.1 to 10 μm, particularly preferably 0.5 to 5 μm.
【0044】次に本発明の感光体を単層構成で形成する
場合、すなわち図3の場合、電荷発生物質及び電荷輸送
物質がバインダ樹脂に含有される割合は、バインダ樹脂
100重量部に対して電荷発生物質は20〜200重量
部、電荷輸送物質は20〜200重量部とされる。この
単層構成の感光体の膜厚は7〜50μm、さらに好まし
くは10〜30μmである。Next, when the photoconductor of the present invention is formed in a single layer structure, that is, in the case of FIG. 3, the ratio of the charge generating substance and the charge transporting substance contained in the binder resin is 100 parts by weight of the binder resin. The charge generation material is 20 to 200 parts by weight, and the charge transport material is 20 to 200 parts by weight. The film thickness of the photoreceptor having this single-layer structure is 7 to 50 μm, more preferably 10 to 30 μm.
【0045】また、前記中間層は接着層またはバリヤ層
等として機能するもので、上記のバインダ樹脂のほか
に、例えばポリビニルアルコール、エチルセルロース、
カルボキシメチルセルロース、塩化ビニル−酢酸ビニル
共重合体、塩化ビニル−酢酸ビニル−無水マレイン酸共
重合体、カゼイン、N−アルコキシメチルナイロン等の
樹脂をそのまま、または酸化スズあるいは酸化インジウ
ムなどを分散させたもの、酸化アルミニウム、酸化亜
鉛、或いは酸化ケイ素などの蒸着膜等が用いられる。中
間層の膜厚は1μm以下が望ましい。The intermediate layer functions as an adhesive layer, a barrier layer, or the like, and in addition to the above binder resin, for example, polyvinyl alcohol, ethyl cellulose,
Resins such as carboxymethyl cellulose, vinyl chloride-vinyl acetate copolymer, vinyl chloride-vinyl acetate-maleic anhydride copolymer, casein, N-alkoxymethyl nylon, etc., as they are, or in which tin oxide, indium oxide, etc. are dispersed A deposited film of aluminum oxide, zinc oxide, silicon oxide, or the like is used. The thickness of the intermediate layer is preferably 1 μm or less.
【0046】また、前記保護層に用いられる材料として
は、前述の樹脂をそのまま使用するか、または酸化スズ
や酸化インジウムなどの低抵抗物質を分散させたものが
適当である。また、有機プラズマ重合膜も使用でき、そ
の有機プラズマ重合膜は、必要に応じて適宜酸素、窒
素、ハロゲン、周期率表の第III族、第V族原子を含ん
でもよい。As the material used for the protective layer, it is suitable to use the above resin as it is or to disperse a low resistance substance such as tin oxide or indium oxide. An organic plasma-polymerized film can also be used, and the organic plasma-polymerized film may optionally contain oxygen, nitrogen, halogen, and Group III or Group V atoms in the periodic table.
【0047】[0047]
【実施例】以下に本発明を実施例を用いてさらに詳しく
説明する。なお、実施例中「部」は特に断わらないかぎ
り「重量部」を意味する。EXAMPLES The present invention will be described in more detail below with reference to examples. In the examples, "parts" means "parts by weight" unless otherwise specified.
【0048】実施例1 下記化学式(A)で表わされるビスアゾ色素5部、ブチ
ラール樹脂(デンカブチラール樹脂#3000−2;電
気化学工業製)2.5部及びテトラヒドロフラン92.
5部をボールミルにて12時間分散させ、次にテトラヒ
ドロフランを2重量%の分散液濃度になるように加え、
再分散させて塗布液を調整した。調整した分散液をアル
ミニウムを蒸着した100μm厚のポリエステルフィル
ム上にドクターブレードにて流延塗布し、乾燥後の膜厚
が1.0μmの電荷発生層を形成した。Example 1 5 parts of a bisazo dye represented by the following chemical formula (A), 2.5 parts of butyral resin (Denka butyral resin # 3000-2; manufactured by Denki Kagaku Kogyo) and tetrahydrofuran 92.
Disperse 5 parts in a ball mill for 12 hours, then add tetrahydrofuran to a dispersion concentration of 2% by weight,
The coating liquid was prepared by redispersion. The prepared dispersion liquid was cast and coated on a 100 μm-thick polyester film on which aluminum was vapor-deposited by a doctor blade to form a charge generation layer having a thickness of 1.0 μm after drying.
【0049】[0049]
【化1】 [Chemical 1]
【0050】このようにして得られた電荷発生層上に、
例示化合物(化合物No.5)6部、及びポリカーボネー
ト樹脂(パンライトK−1300;帝人化成製)10部
メチルフェニールシリコン(KF50 100CPS;
信越化学製)0.002部、テトラヒドロフラン94部
からなる処方の塗布液を調整し、ドクダーブレードにて
流延塗布し、乾燥後の膜厚が20.0μmの電荷輸送層
を形成し、アルミニウム電極/電荷発生層/電荷輸送層
で構成される積層型電子写真感光体(感光体No.1)を
作製した。On the charge generation layer thus obtained,
6 parts of an exemplified compound (Compound No. 5) and 10 parts of a polycarbonate resin (Panlite K-1300; manufactured by Teijin Chemicals) Methylphenylsilicone (KF50 100CPS;
(Shin-Etsu Chemical Co., Ltd.) 0.002 parts of a coating solution having a formulation of 0.004 parts and tetrahydrofuran 94 parts was prepared and cast-cast with a docker blade to form a charge-transporting layer having a film thickness after drying of 20.0 μm. A laminated electrophotographic photosensitive member (photosensitive member No. 1) composed of electrodes / charge generating layer / charge transporting layer was prepared.
【0051】実施例2〜実施例5 実施例1の例示化合物(化合物No.5)の代わりに、例
示化合物中の化合物2、化合物No.3、化合物No.4、
化合物No.6を用いること以外は実施例1と同様の方法
で感光体No.2、感光体No.3、感光体4、感光体No.
5を作製した。 実施例6 上記化学式(A)で表わされるビスアゾ色素5部の代わ
りに、下記化学式(B)で表わされるトリスアゾ色素6
部を用いること以外は実施例1と同様の方法で電荷発生
層を作製した。Examples 2 to 5 Instead of the exemplified compound (Compound No. 5) of Example 1, compound 2, compound No. 3, compound No. 4 in the exemplified compound,
In the same manner as in Example 1 except that the compound No. 6 was used, the photoconductor No. 2, the photoconductor No. 3, the photoconductor 4, the photoconductor No.
5 was produced. Example 6 Instead of 5 parts of the bisazo dye represented by the chemical formula (A) above, a trisazo dye 6 represented by the following chemical formula (B)
A charge generation layer was produced in the same manner as in Example 1 except that the parts were used.
【0052】[0052]
【化2】 [Chemical 2]
【0053】このようにして得られた電荷発生層上に、
例示化合物(化合物No.5)6部、ポリカーボネート樹
脂(パンライトK−1300;帝人化成製)10部、メ
チルフェニールシリコン(KF 100CPS;信越化
学製)0.002部、テトラヒドロフラン94部からな
る塗布液を調整し、実施例1と同様の方法で、乾燥後の
膜厚が20μmの電荷輸送層を形成し、アルミニウム電
極/電荷発生層/電荷輸送層で構成される積層型電子写
真感光体(感光体No.6)を作製した。On the charge generation layer thus obtained,
A coating liquid consisting of 6 parts of an exemplified compound (Compound No. 5), 10 parts of a polycarbonate resin (Panlite K-1300; manufactured by Teijin Chemicals), 0.002 part of methylphenylsilicone (KF 100CPS; manufactured by Shin-Etsu Chemical), and 94 parts of tetrahydrofuran. And a charge transport layer having a film thickness after drying of 20 μm is formed in the same manner as in Example 1, and a laminated electrophotographic photoreceptor (photosensitive layer) composed of an aluminum electrode / charge generation layer / charge transport layer is formed. Body No. 6) was produced.
【0054】実施例7〜実施例10 実施例6例示化合物(化合物No.5)の代わりに、例示
化合物中の化合物No.2、化合物No.3、化合物N
o.4、化合物No.6を用いること以外は実施例6と同様
の方法で感光体No.7、感光体No.8、感光体No.9、
感光体No.10を作製した。Examples 7 to 10 Example 6 Instead of the exemplified compound (Compound No. 5), the compound No. 2, compound No. 3, compound N
O.4, photoconductor No. 7, photoconductor No. 8, photoconductor No. 9, in the same manner as in Example 6 except that compound No. 6 was used.
A photoconductor No. 10 was produced.
【0055】実施例11 チタニルフタロシアニン(TiPc)5部、ポリビニル
ブチラール樹脂(エスレックスBLS;積水化学製)5
部、テトラヒドロフラン90部をボールミルにて12時
間分散させ、次にテトラヒドロフランを2重量%の分散
液濃度になるように加え、再分散させて塗布液を調製し
た。このように調製した塗布液をアルミニウムを約10
00Åの厚さに蒸着した100μm厚のポリエステルフ
ィルム上にドクターブレードにて流延塗布し、乾燥後の
膜厚が0.5μmの電荷発生層を形成した。Example 11 5 parts of titanyl phthalocyanine (TiPc), polyvinyl butyral resin (S-Rex BLS; Sekisui Chemical Co., Ltd.) 5
Parts and 90 parts of tetrahydrofuran were dispersed in a ball mill for 12 hours, and then tetrahydrofuran was added so as to have a dispersion liquid concentration of 2% by weight and redispersed to prepare a coating liquid. The coating solution prepared in this manner was added to about 10 parts of aluminum.
A 100 μm thick polyester film vapor-deposited to a thickness of 00Å was cast and applied by a doctor blade to form a charge generation layer having a thickness of 0.5 μm after drying.
【0056】このようにして得られた電荷発生層上に、
例示化合物(化合物No.5)6部、及びポリカーボネー
ト樹脂(パンライトK−1300;帝人化成製)10
部、テトラヒドロフラン94部からなる処方の塗布液を
調整し、ドクターブレードにて流延塗布し、乾燥後の膜
厚が20.0μmの電荷輸送層を形成し、アルミニウム
電極/電荷発生層/電荷輸送層で形成される積層型電子
写真感光体(感光体No.11)を作製した。On the charge generation layer thus obtained,
Exemplified compound (Compound No. 5) 6 parts and polycarbonate resin (Panlite K-1300; manufactured by Teijin Kasei) 10
Parts, and a coating solution having a formulation of 94 parts of tetrahydrofuran, prepared by flow casting with a doctor blade to form a charge transport layer having a thickness of 20.0 μm after drying, and an aluminum electrode / charge generation layer / charge transport layer. A laminated electrophotographic photosensitive member (photosensitive member No. 11) formed of layers was produced.
【0057】実施例12〜実施例15 実施例11(例示化合物No.5)の代わりに、例示化合
物中の化合物No.2、化合物No.3、化合物No.4、化
合物No.6を用いること以外は実施例11と同様の方法
で感光体No.12、感光体No.13、感光体No.14、
感光体No.15を作製した。Examples 12 to 15 Instead of Example 11 (Exemplified Compound No. 5), Compound No. 2, Compound No. 3, Compound No. 4 and Compound No. 6 in the exemplified compounds were used. Except for the above, in the same manner as in Example 11, photoconductor No. 12, photoconductor No. 13, photoconductor No. 14,
A photoconductor No. 15 was prepared.
【0058】以上のようにして得られた電子写真感光体
について、静電複写紙試験装置(川口電気製作所製:S
P−428)を用いて以下のように特性評価を行った。With respect to the electrophotographic photosensitive member obtained as described above, an electrostatic copying paper test apparatus (Kawaguchi Denki Seisakusho: S
The characteristics were evaluated as follows using P-428).
【0059】+6KVのコロナ帯電を施して、正帯電し
た後、20秒間暗所に放置し、その時の表面電位Voを
測定し、次いでタングステンランプを用いて表面の照度
が40ルックスになるように光照射し、その時Voが半
分になるのに要した露光量をE1/2(lux・se
c)、及び露光後30秒後の表面電位V30を測定した。
その結果を表3に示す。After applying a corona charge of +6 KV and positively charging, it was left in a dark place for 20 seconds, the surface potential Vo at that time was measured, and then light was applied using a tungsten lamp so that the illuminance on the surface was 40 lux. The amount of exposure required to illuminate Vo at that time was halved by E1 / 2 (lux.se
c) and the surface potential V 30 30 seconds after the exposure were measured.
The results are shown in Table 3.
【0060】[0060]
【表11】 [Table 11]
【0061】[0061]
【発明の効果】以上説明したように、本発明に係る電荷
輸送物質として用いるカルコン系化合物は、比較的容易
に合成することができ、かつ、バインダー樹脂中で優れ
た溶解性または分散性を有する。更に、電荷発生物質か
ら発生した電荷を受入れ、それを輸送する能力が優れて
いる。As described above, the chalcone compound used as the charge transport material according to the present invention can be synthesized relatively easily and has excellent solubility or dispersibility in the binder resin. .. Further, it has an excellent ability to receive the charge generated from the charge generating substance and transport it.
【0062】したがって、このカルコン系化合物を含有
する電子写真感光体は、暗減衰率が高く、感度も高い。Therefore, the electrophotographic photoreceptor containing the chalcone compound has a high dark decay rate and a high sensitivity.
【図1】[Figure 1]
【図2】[Fig. 2]
【図3】以上、本発明の電子写真感光体の層構成例を示
すための断面の模式図、FIG. 3 is a schematic cross-sectional view showing an example of the layer structure of the electrophotographic photoreceptor of the present invention.
【図4】実施例1で用いた化合物No.5の赤外線吸収ス
ペクトル図、FIG. 4 is an infrared absorption spectrum diagram of Compound No. 5 used in Example 1.
1 支持体 2 電荷発生層 3 電荷輸送層 4 感光体層(積層構成) 5 保護層 6 感光体層(炭層構成) 1 Support 2 Charge Generation Layer 3 Charge Transport Layer 4 Photoconductor Layer (Layered Structure) 5 Protective Layer 6 Photoconductor Layer (Carbon Layer Structure)
───────────────────────────────────────────────────── フロントページの続き (72)発明者 吉川 雅夫 東京都大田区中馬込1丁目3番6号 株式 会社リコー内 (72)発明者 鈴木 哲郎 東京都大田区中馬込1丁目3番6号 株式 会社リコー内 (72)発明者 下田 昌克 東京都大田区中馬込1丁目3番6号 株式 会社リコー内 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Masao Yoshikawa 1-3-6 Nakamagome, Ota-ku, Tokyo Stock company Ricoh Co., Ltd. (72) Inventor Tetsuro Suzuki 1-3-6 Nakamagome, Ota-ku, Tokyo Shares In Ricoh Company (72) Inventor Masakatsu Shimoda 1-3-6 Nakamagome, Ota-ku, Tokyo
Claims (2)
輸送物質を含有する電子写真感光体において、電荷輸送
物質がカルコン系化合物であることを特徴とする電子写
真感光体。1. An electrophotographic photoreceptor containing a charge generating substance and a charge transporting substance on a conductive support, wherein the charge transporting substance is a chalcone compound.
されるものであることを特徴とする請求項1記載の電子
写真感光体。 ただし、R1及びR2は置換または無置換のフェニル基、
置換または無置換のナフチル基、あるいは複素芳香環基
を表わす。2. The electrophotographic photoreceptor according to claim 1, wherein the chalcone compound is represented by the following general formula I. However, R 1 and R 2 are substituted or unsubstituted phenyl groups,
It represents a substituted or unsubstituted naphthyl group or a heteroaromatic ring group.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP22005291A JPH0561220A (en) | 1991-08-30 | 1991-08-30 | Electrophotographic sensitive body |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP22005291A JPH0561220A (en) | 1991-08-30 | 1991-08-30 | Electrophotographic sensitive body |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH0561220A true JPH0561220A (en) | 1993-03-12 |
Family
ID=16745176
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP22005291A Pending JPH0561220A (en) | 1991-08-30 | 1991-08-30 | Electrophotographic sensitive body |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH0561220A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2001054682A1 (en) * | 2000-01-27 | 2001-08-02 | Takara Bio Inc. | Remedies |
-
1991
- 1991-08-30 JP JP22005291A patent/JPH0561220A/en active Pending
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2001054682A1 (en) * | 2000-01-27 | 2001-08-02 | Takara Bio Inc. | Remedies |
EP1254658A4 (en) * | 2000-01-27 | 2003-06-18 | Takara Bio Inc | Remedies |
KR100711537B1 (en) * | 2000-01-27 | 2007-04-27 | 다카라 바이오 가부시키가이샤 | remedy |
US7268160B2 (en) | 2000-01-27 | 2007-09-11 | Takara Bio, Inc. | Remedies |
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