JPH04285672A - Diphenoquinone-based compound and electrophotographic photosensitive body using the same compound - Google Patents
Diphenoquinone-based compound and electrophotographic photosensitive body using the same compoundInfo
- Publication number
- JPH04285672A JPH04285672A JP5166591A JP5166591A JPH04285672A JP H04285672 A JPH04285672 A JP H04285672A JP 5166591 A JP5166591 A JP 5166591A JP 5166591 A JP5166591 A JP 5166591A JP H04285672 A JPH04285672 A JP H04285672A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- compounds
- diphenoquinone
- compound represented
- 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
- 150000001875 compounds Chemical class 0.000 title abstract description 40
- DDTHMESPCBONDT-UHFFFAOYSA-N 4-(4-oxocyclohexa-2,5-dien-1-ylidene)cyclohexa-2,5-dien-1-one Chemical compound C1=CC(=O)C=CC1=C1C=CC(=O)C=C1 DDTHMESPCBONDT-UHFFFAOYSA-N 0.000 title description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- -1 diphenoquinone compound Chemical class 0.000 claims description 42
- 108091008695 photoreceptors Proteins 0.000 claims description 33
- 239000000758 substrate Substances 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000000463 material Substances 0.000 abstract description 40
- 229920005989 resin Polymers 0.000 abstract description 31
- 239000011347 resin Substances 0.000 abstract description 31
- 239000011230 binding agent Substances 0.000 abstract description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract description 9
- 230000035945 sensitivity Effects 0.000 abstract description 8
- 239000002904 solvent Substances 0.000 abstract description 8
- 239000007800 oxidant agent Substances 0.000 abstract description 6
- 239000012286 potassium permanganate Substances 0.000 abstract description 5
- 150000002989 phenols Chemical class 0.000 abstract description 2
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 37
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- 238000000034 method Methods 0.000 description 11
- 239000002356 single layer Substances 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 4
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 238000000859 sublimation Methods 0.000 description 4
- 230000008022 sublimation Effects 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class 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
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 3
- 239000004417 polycarbonate Substances 0.000 description 3
- 229920000515 polycarbonate Polymers 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- OPKPFEWFKYKJCF-UHFFFAOYSA-N 2-benzylideneindene-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C1=CC1=CC=CC=C1 OPKPFEWFKYKJCF-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 2
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- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 150000004866 oxadiazoles Chemical class 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052711 selenium Inorganic materials 0.000 description 2
- 239000011669 selenium Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- SBFJWYYUVYESMJ-UHFFFAOYSA-N 1-n,1-n,3-n,3-n-tetrakis(3-methylphenyl)benzene-1,3-diamine Chemical compound CC1=CC=CC(N(C=2C=C(C)C=CC=2)C=2C=C(C=CC=2)N(C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)=C1 SBFJWYYUVYESMJ-UHFFFAOYSA-N 0.000 description 1
- AUDVZNJMRRQPFX-UHFFFAOYSA-N 2,3,5,6-tetrakis(trifluoromethyl)phenol Chemical compound OC1=C(C(F)(F)F)C(C(F)(F)F)=CC(C(F)(F)F)=C1C(F)(F)F AUDVZNJMRRQPFX-UHFFFAOYSA-N 0.000 description 1
- WMTYURHKRZDHAM-UHFFFAOYSA-N 2,6-bis(trifluoromethyl)phenol Chemical compound OC1=C(C(F)(F)F)C=CC=C1C(F)(F)F WMTYURHKRZDHAM-UHFFFAOYSA-N 0.000 description 1
- ZOQOPXVJANRGJZ-UHFFFAOYSA-N 2-(trifluoromethyl)phenol Chemical compound OC1=CC=CC=C1C(F)(F)F ZOQOPXVJANRGJZ-UHFFFAOYSA-N 0.000 description 1
- JFJWVJAVVIQZRT-UHFFFAOYSA-N 2-phenyl-1,3-dihydropyrazole Chemical class C1C=CNN1C1=CC=CC=C1 JFJWVJAVVIQZRT-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
- 229910001369 Brass Inorganic materials 0.000 description 1
- 239000004709 Chlorinated polyethylene Substances 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000004641 Diallyl-phthalate Substances 0.000 description 1
- 235000000177 Indigofera tinctoria Nutrition 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 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
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 229920002433 Vinyl chloride-vinyl acetate copolymer Polymers 0.000 description 1
- QLNFINLXAKOTJB-UHFFFAOYSA-N [As].[Se] Chemical compound [As].[Se] QLNFINLXAKOTJB-UHFFFAOYSA-N 0.000 description 1
- 125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
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- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- CECABOMBVQNBEC-UHFFFAOYSA-K aluminium iodide Chemical compound I[Al](I)I CECABOMBVQNBEC-UHFFFAOYSA-K 0.000 description 1
- 229910021417 amorphous silicon Inorganic materials 0.000 description 1
- PGEHNUUBUQTUJB-UHFFFAOYSA-N anthanthrone Chemical class C1=CC=C2C(=O)C3=CC=C4C=CC=C5C(=O)C6=CC=C1C2=C6C3=C54 PGEHNUUBUQTUJB-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 1
- 239000010951 brass Substances 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
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- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
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- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
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- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 1
- 239000005038 ethylene vinyl acetate Substances 0.000 description 1
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- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
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- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
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- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
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- 150000004867 thiadiazoles Chemical class 0.000 description 1
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- 239000011135 tin Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
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- 239000010936 titanium Substances 0.000 description 1
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- 150000004992 toluidines Chemical class 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical class C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 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、新規なジフェノキノン
系化合物とこれを用いた電子写真感光体に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel diphenoquinone compound and an electrophotographic photoreceptor using the same.
【０００２】0002
【従来の技術】近年、複写機、プリンター、ファクシミ
リ等の画像形成装置における電子写真感光体として、加
工性および経済性にすぐれ、機能設計の自由度が大きい
有機感光体が広く使用されている。また、電子写真感光
体を用いて複写画像を形成する場合には、カールソンプ
ロセスが広く利用されている。カールソンプロセスは、
コロナ放電により感光体を均一に帯電させる帯電工程と
、帯電した感光体に原稿像を露光し原稿像に対応した静
電潜像を形成する露光工程と、静電潜像をトナーを含有
する現像剤で現像しトナー像を形成する現像工程と、ト
ナー像を紙などの基材に転写する転写工程と、基材に転
写されたトナー像を定着させる定着工程と、転写工程後
、感光体上に残留するトナーを除去するクリーニング工
程とを含んでいる。このカールソンプロセスにおいて、
高品質の画像を形成するには、電子写真感光体が帯電特
性および感光特性に優れており、かつ露光後の残留電位
が低いことが要求される。BACKGROUND OF THE INVENTION In recent years, organic photoreceptors have been widely used as electrophotographic photoreceptors in image forming apparatuses such as copying machines, printers, facsimile machines, etc., as they are excellent in processability and economical efficiency and have a large degree of freedom in functional design. Further, when forming a copy image using an electrophotographic photoreceptor, the Carlson process is widely used. The Carlson process is
A charging process in which the photoconductor is uniformly charged by corona discharge, an exposure process in which the charged photoconductor is exposed to an original image to form an electrostatic latent image corresponding to the original image, and the electrostatic latent image is developed using toner. A developing process in which a toner image is formed by developing with a toner image, a transfer process in which the toner image is transferred to a base material such as paper, a fixing process in which the toner image transferred to the base material is fixed, and after the transfer process, a toner image is formed on the photoreceptor. and a cleaning step to remove residual toner. In this Carlson process,
In order to form high-quality images, an electrophotographic photoreceptor is required to have excellent charging characteristics and photosensitive characteristics, and to have a low residual potential after exposure.
【０００３】従来より、セレンや硫化カドミウム等の無
機光導電体が電子写真感光体材料として公知であるが、
これらは毒性があり、しかも生産コストが高いという欠
点がある。そこで、これらの無機物質に代えて、種々の
有機物質を用いた、いわゆる有機電子写真感光体が提案
されている。かかる有機電子写真感光体は、露光により
電荷を発生する電荷発生材料と、発生した電荷を輸送す
る機能を有する電荷輸送材料とからなる感光層を有する
。Conventionally, inorganic photoconductors such as selenium and cadmium sulfide have been known as materials for electrophotographic photoreceptors.
These have the disadvantage of being toxic and having high production costs. Therefore, so-called organic electrophotographic photoreceptors using various organic substances in place of these inorganic substances have been proposed. Such an organic electrophotographic photoreceptor has a photosensitive layer composed of a charge-generating material that generates charges upon exposure to light, and a charge-transporting material that has a function of transporting the generated charges.
【０００４】かかる有機電子写真感光体に望まれる各種
の条件を満足させるためには、これら電荷発生材料と電
荷輸送材料との選択を適切に行う必要がある。電荷輸送
材料としては、従来から種々の物質が研究され、ポリビ
ニルカルバゾール、オキサジアゾール系化合物、ピラゾ
リン系化合物、ヒドラゾン系化合物等の多くの物質が提
案されている。これらの電荷輸送材料はホール輸送材料
であるため、現在、有機電子写真感光体の主流となって
いる機能分離型感光体では必然的に負帯電プロセスが要
求される。しかしながら、負極性コロナ放電は本質的に
不安定であり、かつオゾン発生による感光体の劣化、使
用環境の汚染等の問題を有している。これらの問題を解
決するには、電荷輸送材料として電子輸送材料を用いた
正帯電で動作する有機電子写真感光体を採用すれば良く
、電子輸送材料としては特開平１−２０６３４９号公報
に記載されているジフェノキノン構造を有する化合物が
提案されている。このものは非局在化したπ電子系を有
する電子受容体であり、アニオンラジカル状態が関与す
る電子移動反応により電子を輸送することができる。[0004] In order to satisfy various conditions desired for such an organic electrophotographic photoreceptor, it is necessary to appropriately select the charge generating material and the charge transporting material. Various substances have been studied as charge transport materials, and many substances such as polyvinyl carbazole, oxadiazole compounds, pyrazoline compounds, and hydrazone compounds have been proposed. Since these charge transport materials are hole transport materials, a negative charging process is inevitably required in functionally separated photoreceptors, which are currently the mainstream of organic electrophotographic photoreceptors. However, negative polarity corona discharge is inherently unstable and has problems such as deterioration of the photoreceptor due to ozone generation and pollution of the environment in which it is used. In order to solve these problems, it is sufficient to adopt an organic electrophotographic photoreceptor that operates with positive charging and uses an electron transport material as a charge transport material. Compounds with a diphenoquinone structure have been proposed. This is an electron acceptor with a delocalized π-electron system, and can transport electrons through an electron transfer reaction involving an anion radical state.
【０００５】[0005]
【発明が解決しようとする課題】しかしながら、例えば
下記式（Ａ）で示されるように同一置換基Ｃ（ＣＨ３）
３ が対称に配置されたジフェノキノン系化合物は、感
光体を構成する結着樹脂との相溶性が低く、従って量的
に多量のジフェノキノン系化合物を感光層内に含有させ
ることができないため、充分な感度が得られないという
欠点がある。[Problem to be Solved by the Invention] However, for example, as shown in the following formula (A), when the same substituent C(CH3)
A diphenoquinone compound in which 3 is arranged symmetrically has low compatibility with the binder resin constituting the photoreceptor, and therefore a large amount of the diphenoquinone compound cannot be contained in the photosensitive layer. The disadvantage is that sensitivity cannot be obtained.
【０００６】[0006]
【化３】[Chemical formula 3]
【０００７】また、上記ジフェノキノン系化合物は昇華
性を有するため、経時的に感度が低下するおそれもあっ
た。すなわち、ジフェノキノン系化合物の特性は、置換
基のつき方や種類に大きく影響されるものである。本発
明の目的は、かかる技術的課題を解決し、電荷輸送とし
て、結着樹脂との相溶性にすぐれ、かつ昇華性を抑えた
ジフェノキノン系化合物および高感度でかつ繰り返し特
性にすぐれた電子写真感光体を提供することである。[0007] Furthermore, since the diphenoquinone compound has sublimation property, there is also a risk that the sensitivity may decrease over time. That is, the properties of diphenoquinone compounds are greatly influenced by the type and type of substituents. The purpose of the present invention is to solve such technical problems, and to provide a diphenoquinone compound for charge transport that has excellent compatibility with a binder resin and suppresses sublimation, and an electrophotographic photosensitive compound that is highly sensitive and has excellent repeatability. It's about giving your body.
【０００８】[0008]
【課題を解決するための手段および作用】上記の目的を
達成するための本発明のジフェノキノン系化合物は、一
般式（１）：[Means and effects for solving the problems] The diphenoquinone compound of the present invention for achieving the above object has the general formula (1):
【０００９】[0009]
【化４】[C4]
【００１０】（式中、Ｒ１ 、Ｒ２ 、Ｒ３ およびＲ
４ のうち２つの基はアルキル基を、他の２つの基はフ
ッ素置換アルキル基をそれぞれ示し、Ｒ５ およびＲ６
は同一または異なって水素原子またはフッ素置換アル
キル基を示す。）で表されるものである。かかる本発明
のジフェノキノン系化合物は、電子吸引性基としてフッ
素置換アルキル基を使用しているため、高い電子受容性
（電子親和力）を有している。また、アルキル基に導入
されたフッ素原子によって化合物の結着樹脂との相溶性
が向上し、かつ昇華性が低く抑えられている。(wherein R1, R2, R3 and R
4, two groups represent alkyl groups and the other two groups represent fluorine-substituted alkyl groups, R5 and R6
are the same or different and represent a hydrogen atom or a fluorine-substituted alkyl group. ). The diphenoquinone compound of the present invention uses a fluorine-substituted alkyl group as an electron-withdrawing group, and therefore has high electron-accepting properties (electron affinity). Moreover, the compatibility of the compound with the binder resin is improved by the fluorine atom introduced into the alkyl group, and the sublimation property is kept low.
【００１１】さらに、本発明のジフェノキノン系化合物
はその分子中に同一の基が非対称に置換している構造を
有するので、より一層結着樹脂との相溶性にすぐれてい
る。すなわち、本発明のジフェノキノン系化合物には、
例えば下記一般式（１ａ）， （１ｂ）， （１ｃ）で
表されるように、同一置換基が非対称に配置された化合
物が包含されている。下記一般式（１ａ）， （１ｂ）
， （１ｃ）において、一点鎖線Ｙは非対称線を示して
いる。Furthermore, since the diphenoquinone compound of the present invention has a structure in which the same group is asymmetrically substituted in the molecule, it has even better compatibility with the binder resin. That is, the diphenoquinone compound of the present invention includes:
For example, as represented by the following general formulas (1a), (1b), and (1c), compounds in which the same substituents are arranged asymmetrically are included. The following general formulas (1a), (1b)
, (1c), the dashed-dotted line Y indicates an asymmetric line.
【００１２】0012
【化５】[C5]
【００１３】（式中、ｎは１以上の整数である。）従っ
て、本発明の電子写真感光体は、導電性基体上に、上記
一般式（１） で表されるジフェノキノン系化合物を含
有する感光層を設けたことを特徴とする。これにより本
発明の電子写真感光体は、感度および帯電能にすぐれ、
高い繰り返し特性を有する。(In the formula, n is an integer of 1 or more.) Therefore, the electrophotographic photoreceptor of the present invention contains a diphenoquinone compound represented by the above general formula (1) on a conductive substrate. It is characterized by having a photosensitive layer. As a result, the electrophotographic photoreceptor of the present invention has excellent sensitivity and charging ability,
Has high repeatability.
【００１４】前記アルキル基としては、例えばメチル基
、エチル基、プロピル基、イソプロピル基、ブチル基、
イソブチル基、ｔ−ブチル基、ペンチル基、ヘキシル基
などがあげられる。前記フッ素置換アルキル基としては
、例えば１または２以上のフッ素原子が置換したメチル
基、エチル基、プロピル基、イソプロピル基、ブチル基
、イソブチル基、ｔ−ブチル基、ペンチル基、ヘキシル
基などがあげられ、好ましくはトリフルオロメチル基の
ようにアルキル基の有する全ての水素原子がフッ素原子
と置換されたものが好ましい。Examples of the alkyl group include methyl group, ethyl group, propyl group, isopropyl group, butyl group,
Examples include isobutyl group, t-butyl group, pentyl group, and hexyl group. Examples of the fluorine-substituted alkyl group include a methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, pentyl group, hexyl group, etc. substituted with one or more fluorine atoms. Preferably, all hydrogen atoms in an alkyl group are replaced with fluorine atoms, such as a trifluoromethyl group.
【００１５】前記一般式（１） で表されるジフェノキ
ノン系化合物の具体的化合物としては、以下のものを例
示することができる。Specific examples of the diphenoquinone compound represented by the general formula (1) include the following.
【００１６】[0016]
【化６】[C6]
【００１７】前記一般式（１） で表される化合物は、
例えば下記反応式にて製造することができる。
反応式：The compound represented by the above general formula (1) is
For example, it can be produced using the following reaction formula. Reaction formula:
【００１８】[0018]
【化７】[C7]
【００１９】（式中、Ｒ１ 〜Ｒ６ は前記と同じであ
る。）すなわち、式（ａ） で表されるフェノール系化
合物と式（ｂ） で表されるフェノール系化合物を溶剤
に溶解し、酸化剤にて酸化することにより、本発明の化
合物である生成物（１） が得られる（Ｍｅｎｅｇｅｒ
ｅｔ ａｌ．， Ｊ． Ｏｒｇ． Ｃｈｅｍ．， ５
０， ３９２７ （１９８５）を参照） 。(In the formula, R1 to R6 are the same as above.) That is, a phenol compound represented by formula (a) and a phenol compound represented by formula (b) are dissolved in a solvent and oxidized. Product (1), which is a compound of the present invention, is obtained by oxidation with a compound of the present invention (Meneger
et al. , J. Org. Chem. , 5
0, 3927 (1985)).
【００２０】上記溶剤としては、例えばクロロホルム、
ジクロロメタンなどが使用可能である。また、上記酸化
剤としては、例えば過マンガン酸カリウム、フェリシア
ン化カリウムなどが使用可能である。反応は温度５０〜
５５℃程度で加熱することによって行われる。酸化剤の
使用量は、上記フェノール系化合物の１モルに対して４
モル以上が適当である。[0020] Examples of the above solvent include chloroform,
Dichloromethane etc. can be used. Further, as the above-mentioned oxidizing agent, for example, potassium permanganate, potassium ferricyanide, etc. can be used. The reaction takes place at a temperature of 50~
This is done by heating at about 55°C. The amount of oxidizing agent used is 4 to 1 mole of the above phenolic compound.
A mole or more is appropriate.
【００２１】上記反応式においては、生成物として、上
記一般式（１ａ）， （１ｂ）， （１ｃ）で表された
各化合物と置換基の位置が異なる異性体も生成されるが
、カラムクロマトグラフィ等の公知の精製手段により分
離することができる。本発明における感光層は、前記一
般式（１） で表される化合物の１種または２種以上を
含有する。In the above reaction formula, isomers having different substituent positions from the compounds represented by the above general formulas (1a), (1b), and (1c) are also produced as products, but column chromatography It can be separated by known purification means such as. The photosensitive layer in the present invention contains one or more compounds represented by the above general formula (1).
【００２２】本発明における感光層には、電荷発生材料
、電荷輸送材料である前記一般式（１） で表される化
合物および結着樹脂を混合した単層型と、電荷発生層お
よび電荷輸送層を積層した積層型とがあるが、本発明の
感光層はいずれにも適用可能である。積層型の電子写真
感光体を得るには、導電性基材上に電荷発生材料を含有
する電荷発生層を形成し、この電荷発生層上に、電荷輸
送材料である前記一般式で表される化合物を含有する電
荷輸送層を形成すればよい。また、積層順序をこれと逆
にし、電荷輸送層上に電荷発生層を設けるようにしても
よい。The photosensitive layer in the present invention includes a single layer type in which a charge generating material, a charge transporting material, which is a compound represented by the general formula (1), and a binder resin are mixed, and a charge generating layer and a charge transporting layer. There is a laminated type in which the photosensitive layer of the present invention is laminated, and the photosensitive layer of the present invention can be applied to either type. In order to obtain a laminated electrophotographic photoreceptor, a charge generation layer containing a charge generation material is formed on a conductive base material, and a charge transport material represented by the above general formula is placed on the charge generation layer. A charge transport layer containing a compound may be formed. Furthermore, the stacking order may be reversed and the charge generation layer may be provided on the charge transport layer.
【００２３】電荷発生材料としては、従来より使用され
ているセレン、セレン−テルル、セレン−ヒ素、アモル
ファスシリコン、ピリリウム塩、アゾ系化合物、ジスア
ゾ系化合物、フタロシアニン系化合物、アンサンスロン
系化合物、ペリレン系化合物、インジゴ系化合物、トリ
フェニルメタン系化合物、スレン系化合物、トルイジン
系化合物、ピラゾリン系化合物、ペリレン系化合物、キ
ナクリドン系化合物、ピロロピロール系化合物等があげ
られる。これらの電荷発生材料は１種または２種以上を
混合して使用することができる。As charge generating materials, conventionally used selenium, selenium-tellurium, selenium-arsenic, amorphous silicon, pyrylium salts, azo compounds, disazo compounds, phthalocyanine compounds, anthanthrone compounds, and perylene compounds are used. compounds, indigo-based compounds, triphenylmethane-based compounds, threne-based compounds, toluidine-based compounds, pyrazoline-based compounds, perylene-based compounds, quinacridone-based compounds, pyrrolopyrrole-based compounds, and the like. These charge generating materials can be used alone or in combination of two or more.
【００２４】また、電荷輸送材料である前記一般式で表
される化合物は、従来公知の他の電荷輸送材料と組み合
わせて使用することができる。従来公知の電荷輸送材料
としては、例えば２，５−ジ（４−メチルアミノフェニ
ル）−１，３，４−オキサジアゾールなどのオキサジア
ゾール系化合物、９−（４−ジエチルアミノスチリル）
アントラセン等のスチリル系化合物、ポリビニルカルバ
ゾール等のカルバゾール系化合物、１−フェニル−３−
（ｐ−ジメチルアミノフェニル）ピラゾール等のピラゾ
リン系化合物、トリフェニルアミン系化合物、インドー
ル系化合物、オキサゾール系化合物、イソオキサゾール
系化合物、チアゾール系化合物、チアジアゾール系化合
物、イミダゾール系化合物、ピラゾール系化合物、トリ
アゾール系化合物等の含窒素環式化合物、縮合多環式化
合物が例示される。なお、ポリビニルカルバゾール等の
成膜性を有する電荷輸送材料を使用する場合には結着樹
脂は必ずしも必要ではない。[0024] Furthermore, the compound represented by the above general formula, which is a charge transporting material, can be used in combination with other conventionally known charge transporting materials. Conventionally known charge transport materials include, for example, oxadiazole compounds such as 2,5-di(4-methylaminophenyl)-1,3,4-oxadiazole, and 9-(4-diethylaminostyryl).
Styryl compounds such as anthracene, carbazole compounds such as polyvinylcarbazole, 1-phenyl-3-
Pyrazoline compounds such as (p-dimethylaminophenyl) pyrazole, triphenylamine compounds, indole compounds, oxazole compounds, isoxazole compounds, thiazole compounds, thiadiazole compounds, imidazole compounds, pyrazole compounds, triazoles Examples include nitrogen-containing cyclic compounds such as system compounds, and fused polycyclic compounds. Note that a binder resin is not necessarily required when a charge transporting material having film-forming properties such as polyvinylcarbazole is used.
【００２５】前記結着樹脂としては、種々の樹脂が使用
可能であり、例えばスチレン系重合体、スチレン−ブタ
ジエン共重合体、スチレン−アクリロニトリル共重合体
、スチレン−マレイン酸共重合体、アクリル共重合体、
スチレン−アクリル酸共重合体、ポリエチレン、エチレ
ン−酢酸ビニル共重合体、塩素化ポリエチレン、ポリ塩
化ビニル、ポリプロピレン、塩化ビニル−酢酸ビニル共
重合体、ポリエステル、アルキド樹脂、ポリアミド、ポ
リウレタン、ポリカーボネート、ポリアリレート、ポリ
スルホン、ジアリルフタレート樹脂、ケトン樹脂、ホリ
ビニルブチラール樹脂、ポリエーテル樹脂等の熱可塑性
樹脂や、シリコーン樹脂、エポキシ樹脂、その他架橋性
の熱硬化性樹脂、さらにエポキシアクリレート、ウレタ
ン−アクリレートなどの光硬化性樹脂などがあげられる
。これらの結着樹脂は１種または２種以上を混合して用
いることができる。Various resins can be used as the binder resin, such as styrene polymers, styrene-butadiene copolymers, styrene-acrylonitrile copolymers, styrene-maleic acid copolymers, and acrylic copolymers. Union,
Styrene-acrylic acid copolymer, polyethylene, ethylene-vinyl acetate copolymer, chlorinated polyethylene, polyvinyl chloride, polypropylene, vinyl chloride-vinyl acetate copolymer, polyester, alkyd resin, polyamide, polyurethane, polycarbonate, polyarylate , thermoplastic resins such as polysulfone, diallyl phthalate resin, ketone resin, polyvinyl butyral resin, polyether resin, silicone resin, epoxy resin, and other crosslinkable thermosetting resins, as well as photosensitive resins such as epoxy acrylate and urethane-acrylate. Examples include curable resins. These binder resins can be used alone or in combination of two or more.
【００２６】また、電荷発生材料、電荷輸送材料および
結着樹脂を溶解して塗布液をつくるための溶剤としては
、例えばメタノール、エタノール、イソプロパノール、
ブタノール等のアルコール類、ｎ−ヘキサン、オクタン
、シクロヘキサン等の脂肪族系炭化水素、ベンゼン、ト
ルエン、キシレン等の芳香族炭化水素、ジクロロメタン
、ジクロロエタン、四塩化炭素、クロロベンゼン等のハ
ロゲン化炭化水素、ジメチルエーテル、ジエチルエーテ
ル、テトラヒドロフラン、エチレングリコールジメチル
エーテル、ジエチレングリコールジメチルエーテル等の
エーテル類、アセトン、メチルエチルケトン、シクロヘ
キサノン等のケトン類、酢酸エチル、酢酸メチル等のエ
ステル類、ジメチルホルムアルデヒド、ジメチルホルム
アミド、ジメチルスルホキシド等があげられる。
これらの溶剤は１種または２種以上を混合して用いるこ
とができる。[0026] Examples of the solvent for dissolving the charge generating material, charge transporting material and binder resin to prepare a coating solution include methanol, ethanol, isopropanol,
Alcohols such as butanol, aliphatic hydrocarbons such as n-hexane, octane, and cyclohexane, aromatic hydrocarbons such as benzene, toluene, and xylene, halogenated hydrocarbons such as dichloromethane, dichloroethane, carbon tetrachloride, and chlorobenzene, and dimethyl ether. , ethers such as diethyl ether, tetrahydrofuran, ethylene glycol dimethyl ether, and diethylene glycol dimethyl ether, ketones such as acetone, methyl ethyl ketone, and cyclohexanone, esters such as ethyl acetate and methyl acetate, dimethyl formaldehyde, dimethyl formamide, and dimethyl sulfoxide. These solvents can be used alone or in combination of two or more.
【００２７】また、電荷発生層の感度を向上させるため
に、例えばターフェニル、ハロナフトキノン類、アセナ
フチレン等の公知の増感剤を上記電荷発生材料と共に使
用してもよい。さらに、電荷輸送材料や電荷発生材料の
分散性、染工性等をよくするために界面活性剤、レベリ
ング剤等を使用してもよい。Further, in order to improve the sensitivity of the charge generation layer, a known sensitizer such as terphenyl, halonaphthoquinones, acenaphthylene, etc. may be used together with the charge generation material. Furthermore, a surfactant, a leveling agent, etc. may be used to improve the dispersibility, dyeability, etc. of the charge transport material and charge generation material.
【００２８】上記導電性基体としては、例えばアルミニ
ウム、銅、スズ、白金、銀、バナジウム、モリブデン、
クロム、カドミウム、チタン、ニッケル、パラジウム、
インジウム、ステンレス鋼、真鍮等の金属単体や、上記
金属が蒸着またはラミネートされたプラスチック材料、
ヨウ化アルミニウム、酸化スズ、酸化インジウム等で被
覆されたガラス等が例示される。Examples of the conductive substrate include aluminum, copper, tin, platinum, silver, vanadium, molybdenum,
Chromium, cadmium, titanium, nickel, palladium,
Single metals such as indium, stainless steel, and brass, and plastic materials on which the above metals are vapor-deposited or laminated;
Examples include glass coated with aluminum iodide, tin oxide, indium oxide, and the like.
【００２９】導電性基体はシート状、ドラム状などのい
ずれであってもよく、基体自体が導電性を有するか、あ
るいは基体の表面が導電性を有していればよい。また、
基体は、使用に際して、充分な機械的強度を有するもの
が好ましい。積層型電子写真感光体において、電荷発生
層を構成する電荷発生材料と結着樹脂とは種々の割合で
使用することができるが、結着樹脂１００部（重量部、
以下同じ）に対して、電荷発生材料５〜５００部、とく
に１０〜２５０部の割合で用いるのが好ましい。The conductive substrate may be in the form of a sheet or a drum, as long as the substrate itself is conductive or the surface of the substrate is conductive. Also,
The substrate preferably has sufficient mechanical strength during use. In the laminated electrophotographic photoreceptor, the charge generation material and the binder resin constituting the charge generation layer can be used in various ratios, but 100 parts of the binder resin (parts by weight,
It is preferable to use 5 to 500 parts, particularly 10 to 250 parts, of the charge generating material (the same applies hereinafter).
【００３０】また、電荷発生層は、適宜の膜厚を有して
いてもよいが、０．０１〜５μｍ、とくに０．１〜３μ
ｍ程度に形成されるのが好ましい。電荷輸送層を構成す
る上記一般式（１） で表される化合物（電荷輸送材料
）と前記結着樹脂とは種々の割合で使用することができ
るが、光照射により電荷発生層で生じた電荷が容易に輸
送できるように、結着樹脂１００部に対して、上記一般
式で表される化合物を１０〜５００部、とくに２５〜２
００部の割合で用いるのが好ましい。[0030] The charge generation layer may have an appropriate thickness, but it may have a thickness of 0.01 to 5 μm, particularly 0.1 to 3 μm.
It is preferable that the diameter is about m. The compound represented by the above general formula (1) (charge transport material) constituting the charge transport layer and the binder resin can be used in various ratios, but the charge generated in the charge generation layer by light irradiation can be 10 to 500 parts, especially 25 to 2 parts, of the compound represented by the above general formula is added to 100 parts of the binder resin so that it can be easily transported.
Preferably, it is used in a proportion of 0.00 parts.
【００３１】また、電荷輸送層は、２〜１００μｍ、と
くに５〜３０μｍ程度に形成されるのが好ましい。単層
型の電子写真感光体においては、結着樹脂１００部に対
して電荷発生材料は２〜２０部、とくに３〜１５部、上
記一般式で表される化合物（電荷輸送材料）は４０〜２
００部、とくに５０〜１５０部であるのが適当である。
また、単層型の感光層の厚さは１０〜５０μｍ、とくに
１５〜３０μｍ程度であるのが好ましい。The charge transport layer is preferably formed to have a thickness of about 2 to 100 μm, particularly about 5 to 30 μm. In a single-layer type electrophotographic photoreceptor, the amount of the charge generating material is 2 to 20 parts, especially 3 to 15 parts, and the amount of the compound represented by the above general formula (charge transporting material) is 40 to 40 parts per 100 parts of the binder resin. 2
00 parts, especially 50 to 150 parts is suitable. Further, the thickness of the single-layer type photosensitive layer is preferably about 10 to 50 μm, particularly about 15 to 30 μm.
【００３２】電荷発生層および電荷輸送層を含む感光層
を塗布手段により形成する場合には、電荷発生材料また
は電荷輸送材料と結着樹脂とを、従来公知の方法、例え
ばロールミル、ボールミル、アトライタ、ペイントシェ
ーカー、超音波分散器等を用いて塗布液を調製する。When a photosensitive layer including a charge generation layer and a charge transport layer is formed by a coating method, the charge generation material or the charge transport material and the binder resin are mixed by a conventionally known method such as a roll mill, a ball mill, an attritor, or a binder resin. Prepare the coating solution using a paint shaker, ultrasonic disperser, etc.
【００３３】[0033]
【実施例】以下、実施例および比較例をあげて本発明を
詳細に説明する。
実施例１（上記式（２） で表される化合物の合成）Ｍ
ｅｎｅｇｅｒ ｅｔ ａｌ．， Ｊ． Ｏｒｇ． Ｃｈ
ｅｍ．， ５０， ３９２７ （１９８５）に記載の方
法に従って反応を行わせた。すなわち、２，６−ビスト
リフルオロメチルフェノール３．５ｇ（１５ミリモル）
と、２，６−ジメチルフェノール１．８ｇ（１５ミリ
モル） とをクロロホルム６５ｍｌに溶解させ、さらに
酸化剤として過マンガン酸カリウム１９ｇ（１２０ミリ
モル）を加え、５５℃で２時間攪拌した。ついで、反応
混合物から不溶物をろ別したのち、溶媒を留去して反応
混合物を得た。ついで、この反応混合物をエタノール可
溶分と不溶分とに分け、前者はさらにエタノール／クロ
ロホルムから再結晶化し、カラムクロマトグラフィで精
製して、上記式（２） で表される化合物を得た。
元素分析値：Ｃ１６Ｈ１０Ｏ２ Ｆ６ として計算値（
％） Ｃ５５．１８ Ｈ２．９０実測値（％
） Ｃ５５．１０ Ｈ２．９８実施例２（上
記式（３） で表される化合物の合成）２−メチル−６
−トリフルオロメチルフェノール５．３ｇ（３０ミリモ
ル）をクロロホルム６５ｍｌに溶解させ、さらに酸化剤
として過マンガン酸カリウム１９ｇ（１２０ミリモル）
を加え、５５℃で２時間攪拌した。ついで、反応混合物
から不溶物をろ別したのち、溶媒を留去して反応混合物
を得た。ついで、この反応混合物をエタノール可溶分と
不溶分とに分け、前者はさらにエタノール／クロロホル
ムから再結晶化し、カラムクロマトグラフィで精製して
、上記式（３） で表される化合物を得た。
元素分析値：Ｃ１６Ｈ１０Ｏ２ Ｆ６ として計算値（
％） Ｃ５５．１８ Ｈ２．９０実測値（％
） Ｃ５５．２３ Ｈ２．８２実施例３（上
記式（４） で表される化合物の合成）２，３，５，６
−テトラキストリフルオロメチルフェノール５．５ｇ（
１５ミリモル）と、２，６−ジメチルフェノール１．８
ｇ（１５ミリモル）とをクロロホルム６５ｍｌに溶解さ
せ、さらに酸化剤として過マンガン酸カリウム１９ｇ（
１２０ミリモル）を加え、５５℃で２時間攪拌した。つ
いで、反応混合物から不溶物をろ別したのち、溶媒を留
去し、ついでエタノール／クロロホルムから再結晶化し
、さらにカラムクロマトグラフィで精製して、上記式（
４） で表される化合物を得た。
元素分析値：Ｃ１８Ｈ８ Ｏ２ Ｆ１２として計算値（
％） Ｃ４４．６４ Ｈ１．６７実測値（％
） Ｃ４４．５１ Ｈ１．７３実施例４（積
層型感光層）
電荷発生材料としての無金属フタロシアニン（ＸＨ２Ｐ
ｃ）１部、ポリビニルブチラール樹脂（積水化学工業社
製の「Ｓ−ｌｅｃＢＭ−５）」１部、テトラヒドロフラ
ン１２０部を、ジルコニアビーズ（２ｍｍ径） を用い
たペイントシェーカーにて２時間分散させた。得られた
分散液をアルミニウムシート上にワイヤーバーを用いて
塗工し、１００℃で１時間乾燥し、０．５μｍの電荷発
生層を得た。[Examples] The present invention will be explained in detail below with reference to Examples and Comparative Examples. Example 1 (Synthesis of compound represented by the above formula (2)) M
Eneger et al. , J. Org. Ch
em. , 50, 3927 (1985). That is, 3.5 g (15 mmol) of 2,6-bistrifluoromethylphenol.
and 1.8 g (15 mmol) of 2,6-dimethylphenol were dissolved in 65 ml of chloroform, and 19 g (120 mmol) of potassium permanganate was added as an oxidizing agent, followed by stirring at 55°C for 2 hours. Then, after filtering out insoluble matter from the reaction mixture, the solvent was distilled off to obtain a reaction mixture. Next, this reaction mixture was divided into an ethanol-soluble fraction and an ethanol-insoluble fraction, and the former was further recrystallized from ethanol/chloroform and purified by column chromatography to obtain the compound represented by the above formula (2). Elemental analysis value: Calculated value as C16H10O2 F6 (
%) C55.18 H2.90 actual value (%
) C55.10 H2.98 Example 2 (Synthesis of compound represented by the above formula (3)) 2-methyl-6
- 5.3 g (30 mmol) of trifluoromethylphenol was dissolved in 65 ml of chloroform, and 19 g (120 mmol) of potassium permanganate was added as an oxidizing agent.
was added and stirred at 55°C for 2 hours. Then, after filtering out insoluble matter from the reaction mixture, the solvent was distilled off to obtain a reaction mixture. This reaction mixture was then divided into an ethanol-soluble fraction and an ethanol-insoluble fraction, and the former was further recrystallized from ethanol/chloroform and purified by column chromatography to obtain the compound represented by the above formula (3). Elemental analysis value: Calculated value as C16H10O2 F6 (
%) C55.18 H2.90 actual value (%
) C55.23 H2.82 Example 3 (Synthesis of compound represented by the above formula (4)) 2,3,5,6
- Tetrakistrifluoromethylphenol 5.5g (
15 mmol) and 2,6-dimethylphenol 1.8
g (15 mmol) in 65 ml of chloroform, and further added 19 g of potassium permanganate (15 mmol) as an oxidizing agent.
120 mmol) was added thereto, and the mixture was stirred at 55°C for 2 hours. Then, after filtering off insoluble matter from the reaction mixture, the solvent was distilled off, and then recrystallized from ethanol/chloroform, and further purified by column chromatography to obtain the above formula (
4) A compound represented by the following was obtained. Elemental analysis value: Calculated value as C18H8 O2 F12 (
%) C44.64 H1.67 Actual value (%
) C44.51 H1.73 Example 4 (Laminated photosensitive layer) Metal-free phthalocyanine (XH2P
c) 1 part of polyvinyl butyral resin (S-lecBM-5 manufactured by Sekisui Chemical Co., Ltd.) and 120 parts of tetrahydrofuran were dispersed for 2 hours in a paint shaker using zirconia beads (2 mm diameter). The resulting dispersion was applied onto an aluminum sheet using a wire bar and dried at 100° C. for 1 hour to obtain a charge generation layer of 0.5 μm.
【００３４】この電荷発生層上に、実施例１で得た上記
式（２） で表されるジフェノキノン系化合物（電荷輸
送材料）７５部およびポリ（４，４’−シクロヘキシリ
デンジフェニル）カーボネート樹脂（三菱瓦斯化学社製
の「ポリカーボネートＺ−２００」）１００部を所定量
のトルエンに溶解した溶液をワイヤーバーにて塗工し、
１００℃で１時間乾燥し、２２μｍの電荷輸送層を形成
し、正帯電型の電子写真感光体を得た。
実施例５（積層型感光層）
上記式（２） で表されるジフェノキノン系化合物に代
えて、実施例２で得た式（３） で表されるジフェノキ
ノン系化合物を用いたほかは実施例４と同様にして正帯
電型の電子写真感光体を得た。
実施例６（積層型感光層）
上記式（２） で表されるジフェノキノン系化合物に代
えて、実施例３で得た式（４） で表されるジフェノキ
ノン系化合物を用いたほかは実施例４と同様にして正帯
電型の電子写真感光体を得た。
比較例１（積層型感光層）
電荷輸送材料として、下記式（Ａ）：On this charge generation layer, 75 parts of the diphenoquinone compound (charge transport material) represented by the above formula (2) obtained in Example 1 and poly(4,4'-cyclohexylidene diphenyl) carbonate resin were applied. A solution of 100 parts of "Polycarbonate Z-200" manufactured by Mitsubishi Gas Chemical Co., Ltd. dissolved in a predetermined amount of toluene was applied with a wire bar.
It was dried at 100° C. for 1 hour to form a charge transport layer of 22 μm, thereby obtaining a positively charged electrophotographic photoreceptor. Example 5 (Laminated photosensitive layer) Example 4 except that the diphenoquinone compound represented by formula (3) obtained in Example 2 was used instead of the diphenoquinone compound represented by formula (2) above. A positively charged electrophotographic photoreceptor was obtained in the same manner as above. Example 6 (Laminated photosensitive layer) Example 4 except that the diphenoquinone compound represented by formula (4) obtained in Example 3 was used instead of the diphenoquinone compound represented by formula (2) above. A positively charged electrophotographic photoreceptor was obtained in the same manner as above. Comparative Example 1 (Laminated Photosensitive Layer) As a charge transport material, the following formula (A):
【００３５】[0035]
【化８】[Chemical formula 8]
【００３６】で表されるジフェノキノン系化合物を樹脂
１００部に対して３０部の割合で使用したほかは実施例
１と同様にして正帯電型の電子写真感光体を得た。この
ジフェノキノン系化合物の添加量を３０部としたのは、
この化合物が結着樹脂に溶解する限界であり、これ以上
溶解させることができなかったからである。
実施例７（単層型感光層）
（成分）
（部
） 無金属フタロシアニン
１
結着樹脂
１００ （
前出の「ポリカーボネートＺ−２００」）
上記式（３） で表されたジフェノキ
ノン系化合物 ６０ Ｎ，Ｎ，Ｎ’，
Ｎ’−テトラキス（３− メチルフェ ニル
）−１，３−ジアミノベンゼン
４０これらの各成分を所定量のテト
ラヒドロフラン中に加え、ジルコニアビーズ（２ｍｍ径
） を用いたペイントシェーカーにて２ 時間分散させ
た。得られた分散液をアルミニウムシート上にワイヤー
バーを用いて塗工し、１００℃で１時間乾燥し、２０μ
ｍの感光層を形成し、単層型の電子写真感光体を得た。
実施例８（単層型感光層）
上記式（２） で表されるジフェノキノン系化合物に代
えて、実施例２で得た式（３） で表されるジフェノキ
ノン系化合物を用いたほかは実施例７と同様にして単層
型の電子写真感光体を得た。
実施例９（単層型感光層）
上記式（２） で表されるジフェノキノン系化合物に代
えて、実施例３で得た式（４） で表されるジフェノキ
ノン系化合物を用いたほかは実施例７と同様にして単層
型の電子写真感光体を得た。
比較例２（単層型感光層）
電荷輸送材料として、上記式（２） で表されたジフェ
ノキノン系化合物に代えて、上記式（Ａ）で表されたジ
フェノキノン系化合物を用いたほかは実施例２と同様に
して、電子写真感光体を得た。ただし、使用したジフェ
ノキノン系化合物（Ａ）の添加量は上記比較例１と同じ
３０部とした。A positively charged electrophotographic photoreceptor was obtained in the same manner as in Example 1, except that the diphenoquinone compound represented by the formula was used at a ratio of 30 parts to 100 parts of the resin. The reason why the amount of diphenoquinone compound added was 30 parts was because
This is because this compound reached the limit of its solubility in the binder resin and could not be dissolved any further. Example 7 (single layer type photosensitive layer) (components)
(Part) Metal-free phthalocyanine
1
Binder resin
100 (
"Polycarbonate Z-200" mentioned above)
Diphenoquinone compound represented by the above formula (3) 60 N, N, N',
N'-tetrakis(3-methylphenyl)-1,3-diaminobenzene
40 Each of these components was added to a predetermined amount of tetrahydrofuran and dispersed for 2 hours using a paint shaker using zirconia beads (2 mm diameter). The resulting dispersion was coated onto an aluminum sheet using a wire bar, dried at 100°C for 1 hour, and coated with a 20μ
m photosensitive layers were formed to obtain a single-layer type electrophotographic photoreceptor. Example 8 (Single-layer type photosensitive layer) Same as Example except that the diphenoquinone compound represented by formula (3) obtained in Example 2 was used instead of the diphenoquinone compound represented by formula (2) above. A single-layer electrophotographic photoreceptor was obtained in the same manner as in Example 7. Example 9 (single-layer photosensitive layer) Same as Example except that the diphenoquinone compound represented by formula (4) obtained in Example 3 was used instead of the diphenoquinone compound represented by formula (2) above. A single-layer electrophotographic photoreceptor was obtained in the same manner as in Example 7. Comparative Example 2 (Single-layer type photosensitive layer) Example except that the diphenoquinone compound represented by the above formula (A) was used instead of the diphenoquinone compound represented by the above formula (2) as the charge transport material. An electrophotographic photoreceptor was obtained in the same manner as in 2. However, the amount of diphenoquinone compound (A) used was 30 parts, the same as in Comparative Example 1 above.
【００３７】（評価試験）各実施例および比較例で得た
感光体の表面電位、半減露光量（Ｅ１／２ ）および残
留電位を評価試験機（川口電気社製の「ＥＰＡ８１００
」）にて測定した。測定条件は以下の通りである。
光強度：１０μＷ／ｃｍ２
露光時間：２秒
表面電位：（±）７００Ｖ付近となるように流れ込み電
流値を調整した。(Evaluation test) The surface potential, half-decreased exposure (E1/2), and residual potential of the photoreceptor obtained in each example and comparative example were measured using an evaluation tester ("EPA8100" manufactured by Kawaguchi Electric Co., Ltd.).
”). The measurement conditions are as follows. Light intensity: 10 μW/cm 2 Exposure time: 2 seconds Surface potential: The inflow current value was adjusted to be around (±)700V.
【００３８】光源：７８０ｎｍの光
除電：２００ルクス
残留電位測定：露光開始後１秒後の電位を測定した。
実施例４〜９および比較例１〜２の試験結果を表１に示
す。なお、実施例７〜９および比較例２の単層型感光層
を有する感光体は、正帯電および負帯電のそれぞれにつ
いて試験した。。Light source: 780 nm light Static elimination: 200 lux Measurement of residual potential: The potential was measured 1 second after the start of exposure. The test results of Examples 4 to 9 and Comparative Examples 1 to 2 are shown in Table 1. The photoreceptors having single-layer photosensitive layers of Examples 7 to 9 and Comparative Example 2 were tested for positive charging and negative charging, respectively. .
【００３９】[0039]
【表１】[Table 1]
【００４０】この試験結果から、実施例の感光体は比較
例のものに比べて半減露光量および残留電位がすぐれて
おり、感度が著しく改善されていることがわかる。From the test results, it can be seen that the photoreceptors of the examples are superior in half-life exposure and residual potential, and have significantly improved sensitivity, compared to those of the comparative examples.
【００４１】[0041]
【発明の効果】以上のように本発明のジフェノキノン系
化合物は、結着樹脂との相溶性にすぐれ、かつ昇華性が
低いために、このジフェノキノン系化合物を用いた本発
明の電子写真感光体は感度および繰り返し特性にすぐれ
ているという効果がある。Effects of the Invention As described above, the diphenoquinone compound of the present invention has excellent compatibility with the binder resin and has low sublimation property. Therefore, the electrophotographic photoreceptor of the present invention using this diphenoquinone compound It has the advantage of having excellent sensitivity and repeatability.
Claims (2)
つの基はアルキル基を、他の２つの基はフッ素置換アル
キル基をそれぞれ示し、Ｒ５ およびＲ６ は同一また
は異なって水素原子またはフッ素置換アルキル基を示す
。）で表されるジフェノキノン系化合物。Claim 1: General formula (1): [Formula 1] (wherein, 2 of R1, R2, R3 and R4
One group represents an alkyl group, the other two groups represent a fluorine-substituted alkyl group, and R5 and R6 are the same or different and represent a hydrogen atom or a fluorine-substituted alkyl group. ) is a diphenoquinone compound represented by
されるジフェノキノン系化合物を含有する感光層を設け
たことを特徴とする電子写真感光体。 【化２】 （式中、Ｒ１ 、Ｒ２ 、Ｒ３ およびＲ４ のうち２
つの基はアルキル基を、他の２つの基はフッ素置換アル
キル基をそれぞれ示し、Ｒ５ およびＲ６ は同一また
は異なって水素原子またはフッ素置換アルキル基を示す
。）2. An electrophotographic photoreceptor characterized in that a photosensitive layer containing a diphenoquinone compound represented by the following general formula (1) is provided on a conductive substrate. [Formula 2] (wherein, 2 of R1, R2, R3 and R4
One group represents an alkyl group, the other two groups represent a fluorine-substituted alkyl group, and R5 and R6 are the same or different and represent a hydrogen atom or a fluorine-substituted alkyl group. )
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5166591A JPH04285672A (en) | 1991-03-15 | 1991-03-15 | Diphenoquinone-based compound and electrophotographic photosensitive body using the same compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5166591A JPH04285672A (en) | 1991-03-15 | 1991-03-15 | Diphenoquinone-based compound and electrophotographic photosensitive body using the same compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH04285672A true JPH04285672A (en) | 1992-10-09 |
Family
ID=12893179
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5166591A Pending JPH04285672A (en) | 1991-03-15 | 1991-03-15 | Diphenoquinone-based compound and electrophotographic photosensitive body using the same compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH04285672A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003077894A1 (en) * | 2002-03-12 | 2003-09-25 | University Of Iowa Research Foundation | Fluorine-substituted alkyl phenol compounds and their uses |
-
1991
- 1991-03-15 JP JP5166591A patent/JPH04285672A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003077894A1 (en) * | 2002-03-12 | 2003-09-25 | University Of Iowa Research Foundation | Fluorine-substituted alkyl phenol compounds and their uses |
| US7312250B2 (en) | 2002-03-12 | 2007-12-25 | University Of Iowa Research Foundation | Fluorine-substituted alkyl phenol compounds and their uses |
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