JPH03256050A - Bichargeable organic sensitive body for electrophotography - Google Patents
Bichargeable organic sensitive body for electrophotographyInfo
- Publication number
- JPH03256050A JPH03256050A JP5382790A JP5382790A JPH03256050A JP H03256050 A JPH03256050 A JP H03256050A JP 5382790 A JP5382790 A JP 5382790A JP 5382790 A JP5382790 A JP 5382790A JP H03256050 A JPH03256050 A JP H03256050A
- Authority
- JP
- Japan
- Prior art keywords
- charge
- weight
- parts
- diphenoquinone
- substance
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 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 claims abstract description 47
- 239000000463 material Substances 0.000 claims abstract description 25
- 239000002356 single layer Substances 0.000 claims abstract description 18
- 108091008695 photoreceptors Proteins 0.000 claims description 56
- 239000000126 substance Substances 0.000 claims description 53
- 230000005525 hole transport Effects 0.000 claims description 29
- 239000000203 mixture Substances 0.000 claims description 8
- 230000035945 sensitivity Effects 0.000 abstract description 15
- 239000006185 dispersion Substances 0.000 abstract description 4
- 230000003993 interaction Effects 0.000 abstract description 3
- 238000003475 lamination Methods 0.000 abstract description 2
- 239000003989 dielectric material Substances 0.000 abstract 2
- 230000027756 respiratory electron transport chain Effects 0.000 abstract 1
- 230000032258 transport Effects 0.000 description 33
- 239000010410 layer Substances 0.000 description 32
- 239000011248 coating agent Substances 0.000 description 21
- 238000000576 coating method Methods 0.000 description 21
- 229910052757 nitrogen Inorganic materials 0.000 description 21
- 229920005989 resin Polymers 0.000 description 16
- 239000011347 resin Substances 0.000 description 16
- 239000000049 pigment Substances 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- -1 tetraphenylmetaphenylenediamine compound Chemical class 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 229920000548 poly(silane) polymer Polymers 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000011230 binding agent Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 4
- 238000002360 preparation method Methods 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
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-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
- 150000001875 compounds Chemical class 0.000 description 3
- 239000011888 foil Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 3
- 239000004417 polycarbonate Substances 0.000 description 3
- 229920000515 polycarbonate Polymers 0.000 description 3
- 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 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 102100039497 Choline transporter-like protein 3 Human genes 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-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
- 101000889279 Homo sapiens Choline transporter-like protein 3 Proteins 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-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
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 150000002576 ketones Chemical class 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
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000002861 polymer material Substances 0.000 description 2
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- VEUMBMHMMCOFAG-UHFFFAOYSA-N 2,3-dihydrooxadiazole Chemical compound N1NC=CO1 VEUMBMHMMCOFAG-UHFFFAOYSA-N 0.000 description 1
- CLQYLLIGYDFCGY-UHFFFAOYSA-N 4-(2-anthracen-9-ylethenyl)-n,n-diethylaniline Chemical compound C1=CC(N(CC)CC)=CC=C1C=CC1=C(C=CC=C2)C2=CC2=CC=CC=C12 CLQYLLIGYDFCGY-UHFFFAOYSA-N 0.000 description 1
- 229910001369 Brass Inorganic materials 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
- 239000004641 Diallyl-phthalate Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 235000000177 Indigofera tinctoria Nutrition 0.000 description 1
- GWESVXSMPKAFAS-UHFFFAOYSA-N Isopropylcyclohexane Natural products CC(C)C1CCCCC1 GWESVXSMPKAFAS-UHFFFAOYSA-N 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
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-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
- 238000010521 absorption reaction Methods 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 229920006243 acrylic copolymer Polymers 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 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
- 229920006125 amorphous polymer Polymers 0.000 description 1
- 229910021417 amorphous silicon Inorganic materials 0.000 description 1
- PGEHNUUBUQTUJB-UHFFFAOYSA-N anthanthrone Chemical compound 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
- 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
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- GNEPOXWQWFSSOU-UHFFFAOYSA-N dichloro-methyl-phenylsilane Chemical compound C[Si](Cl)(Cl)C1=CC=CC=C1 GNEPOXWQWFSSOU-UHFFFAOYSA-N 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- AZMMUMQYPBKXHS-UHFFFAOYSA-N gold sodium Chemical compound [Na].[Au] AZMMUMQYPBKXHS-UHFFFAOYSA-N 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 229940097275 indigo Drugs 0.000 description 1
- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 230000009878 intermolecular interaction Effects 0.000 description 1
- 229920000554 ionomer Polymers 0.000 description 1
- 150000002545 isoxazoles Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 150000002916 oxazoles Chemical class 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 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
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 125000005372 silanol group Chemical group 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 229920001909 styrene-acrylic polymer Polymers 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 150000004992 toluidines Chemical class 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
- 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
【発明の詳細な説明】
［産業上の利用分野］
本発明は、両帯電可能な電子写真用有機感光体に関する
もので、より詳細には、電荷発生物質と電荷輸送物質を
組合せで含有する有機感光体の改良に関する。Detailed Description of the Invention [Field of Industrial Application] The present invention relates to an organic photoreceptor for electrophotography that can be charged with both charges, and more particularly, it relates to an organic photoreceptor containing a combination of a charge-generating substance and a charge-transporting substance. Regarding improvement of photoreceptors.
［従来の技術］
電子写真感光体の分野では、電荷発生層（ＣＧＬ）と電
荷輸送層（ＣＴＬ）とを積層した所謂機能分離型の有機
感光体が次第に使用されるに至っている。[Prior Art] In the field of electrophotographic photoreceptors, so-called functionally separated organic photoreceptors in which a charge generation layer (CGL) and a charge transport layer (CTL) are stacked are increasingly being used.
この積層型の感光体と共に、電荷輸送物質の媒体中に電
荷発生物質を分散させた単層分散型の有機感光体も既に
知られている。In addition to this laminated type photoreceptor, a single-layer dispersed type organic photoreceptor in which a charge generating substance is dispersed in a medium of a charge transporting substance is already known.
この種の感光体の電荷輸送物質としては、キャリヤ移動
度の高いものが要求されており、初期のポリビニルカル
バゾール（ＰＶＫ）のような高分子材料から、樹脂分散
系で用いる低分子化合物材料へと移行してきている。し
かしながら、成形加工性の点から言えば、電荷輸送物質
は、単一で使用可能な造膜性物質が望ましい。前述した
ＰＶＫは造膜可能であるが、隣接カルバゾール環が形成
するダイマーサイトが構造的なホールキャリヤトラップ
として働き、感光体の電子写真特性の低下を引き起こす
という問題がある。Charge transport materials for this type of photoreceptor are required to have high carrier mobility, and there has been a shift from early polymer materials such as polyvinylcarbazole (PVK) to low-molecular compound materials used in resin dispersion systems. It is transitioning. However, from the viewpoint of moldability, it is desirable that the charge transport material be a film-forming material that can be used alone. Although the above-mentioned PVK can be used to form a film, there is a problem in that dimer sites formed by adjacent carbazole rings act as structural hole carrier traps, causing deterioration of the electrophotographic properties of the photoreceptor.
最近に至って、特開昭６１−１７０７４７号公報には、
有機ポリシランを正孔輸送材料として含む感光体が提案
されている。この有機ポリシランは溶液からの成膜が可
能であり、非晶質高分子材料の中では高いホールドリフ
ト移動度（〜１０−’ｃｍ”／Ｖ−ｓｅｅ）を示すこと
も知られてぃる。Recently, Japanese Unexamined Patent Application Publication No. 170747/1983 states that
Photoreceptors containing organic polysilane as a hole transport material have been proposed. This organic polysilane can be formed into a film from a solution, and is also known to exhibit high hold lift mobility (~10-'cm''/V-see) among amorphous polymer materials.
従来提案されている電荷輸送物質は一般に正孔輸送性の
ものが殆んどであり、電子輸送能を有する数少ない例と
して、特開平１−２０６３４９号公報には、ジフェノキ
ノン構造を有する化合物が電子写真感光体用電荷輸送剤
として提案されている。Most of the charge transport materials that have been proposed so far have hole transport properties, and as one of the few examples that have electron transport ability, Japanese Patent Application Laid-open No. 1-206349 describes a compound with a diphenoquinone structure that can be used for electrophotography. It has been proposed as a charge transport agent for photoreceptors.
［発明が解決しようとする問題点］
従来、複写機等の分野で実用に供されている有機感光体
の殆んどは負帯電で動作するものであり、オゾンの発生
等の欠点があることから、正帯電型有機感光体が切望さ
れている。[Problems to be solved by the invention] Conventionally, most of the organic photoreceptors that have been put to practical use in the field of copying machines, etc. operate with negative charge, and have drawbacks such as the generation of ozone. Therefore, positively charged organic photoreceptors are desired.
前述したジフェノキノン誘導体は結着剤樹脂との相溶性
もよく、良好な電子輸送能を示すと言われているが、こ
のジフェノキノン誘導体を用いた積層感光体では、未だ
残留電位が高く、実用面での感度が十分でないという欠
点がある。The above-mentioned diphenoquinone derivative is said to have good compatibility with the binder resin and exhibit good electron transport ability, but laminated photoreceptors using this diphenoquinone derivative still have a high residual potential and are not suitable for practical use. The disadvantage is that the sensitivity is not sufficient.
一方、感光体の帯電極性について言えば、正帯電及び負
帯電の両方の極性で用いることができれば、感光体の応
用範囲を更に広げることができ、有利である。On the other hand, regarding the charging polarity of the photoreceptor, it would be advantageous if the photoreceptor could be used with both positive and negative polarities, since it would further expand the range of applications of the photoreceptor.
従って、本発明の目的は、電荷発生物質と電荷輸送物質
とを含有する有機感光体において、両方の極性での帯電
が可能で、残留電位が低いレベルに抑制されると共に両
方の極性での帯電に対して優れた感度を示す有機感光体
を提供するにある。Therefore, an object of the present invention is to provide an organic photoreceptor containing a charge-generating substance and a charge-transporting substance, which can be charged with both polarities, suppress the residual potential to a low level, and which can be charged with both polarities. An object of the present invention is to provide an organic photoreceptor that exhibits excellent sensitivity to.
本発明の他の目的は、耐光性が向上し且つ耐刷性にも優
れた電子写真用有機感光体を提供するにある。Another object of the present invention is to provide an organic photoreceptor for electrophotography that has improved light resistance and excellent printing durability.
［問題点を解決するための手段］
本発明によれば、電荷発生物質及び電荷輸送物質を積層
型でまたは単層分散型で含有する電子写真用有機感光体
において、電荷輸送物質が正孔輸送物質１００重量部当
り３０重量部よりも多い量のジフェノキノン誘導体を含
有する、組成物から成ることを特徴とする両帯電可能な
電子写真用有機感光体が提案される。[Means for Solving the Problems] According to the present invention, in an electrophotographic organic photoreceptor containing a charge-generating substance and a charge-transporting substance in a layered form or a monolayer dispersed form, the charge-transporting substance transports holes. A bichartable electrophotographic organophotoreceptor is proposed, characterized in that it consists of a composition containing more than 30 parts by weight of a diphenoquinone derivative per 100 parts by weight of substance.
ジフェノキノン誘導体は、正孔輸送物質１００重量部当
り３０重量部以上、特に３０乃至３００重量部の量で用
いることが、前述した本発明の目的に好ましく、正孔輸
送物質は、有機ポリシランのようにそれ自体樹脂として
の作用を兼ねるものでもよく、また低分子正孔輸送物質
のように、樹脂との組合せで使用するものでもよい。The diphenoquinone derivative is preferably used in an amount of 30 parts by weight or more, particularly 30 to 300 parts by weight, per 100 parts by weight of the hole transport substance for the purpose of the present invention, and the hole transport substance is preferably used in an amount such as organic polysilane. It may itself function as a resin, or it may be used in combination with a resin, such as a low-molecular hole transport substance.
［作用］
本発明は、種々の電子輸送物質の内でもジフェノキノン
誘導体を選択し、これを正孔輸送物質中に成る一定量以
上の量で配合すると、正帯電及び負帯電の両方に対して
優れた感度を示すという発見に基ずくものである。[Function] In the present invention, when a diphenoquinone derivative is selected from among various electron-transporting substances and is blended in a certain amount or more in a hole-transporting substance, the diphenoquinone derivative is excellent against both positive and negative charging. This is based on the discovery that it exhibits high sensitivity.
添付図面第１図は、正孔輸送物質（テトラフェニルメタ
フェニレンジアミン系化合物）と、電子輸送物質として
のジフェノキノン誘導体との配合比を変化させて、正帯
電時及び負帯電時の感度をプロットさせたものである。Figure 1 of the attached drawing shows the plot of the sensitivity during positive charging and negative charging by changing the compounding ratio of a hole transporting substance (tetraphenylmetaphenylenediamine compound) and a diphenoquinone derivative as an electron transporting substance. It is something that
この第１図を参照すると、両者の組成物から成る電荷輸
送性物質は、かなり広く組成範囲内で、正帯電に対して
も、負帯電に対しても優れた感度を示すという予想外の
事実が明らかとなる。Referring to Fig. 1, it is an unexpected fact that charge transport materials composed of both compositions exhibit excellent sensitivity to both positive and negative charges within a fairly wide composition range. becomes clear.
一般に、正孔輸送物質に電子受容性の物質を添加すると
、両者間での電荷移動のような相互作用のため、全体と
しての電荷移動度の低下を引き起こし、このため感光体
の感度が低下する。しかしながら、本発明で使用するジ
フェノキノン誘導体は電子輸送が効率よく起こる濃度以
上に添加した場合にさえ、相互作用による電荷移動度の
低下を来さないという例外的な作用を示し、かくして負
帯電時の感度を損なうことなく、正帯電時にも良好な感
度を示す。In general, when an electron-accepting substance is added to a hole-transporting substance, the overall charge mobility decreases due to interactions such as charge transfer between the two, which reduces the sensitivity of the photoreceptor. . However, the diphenoquinone derivative used in the present invention exhibits an exceptional effect of not causing a decrease in charge mobility due to interaction even when added at a concentration higher than that at which electron transport occurs efficiently. Shows good sensitivity even when positively charged without impairing sensitivity.
加えて本発明で用いるジフェノキノン誘導体は、種々の
電子受容性物質の中でも、帯電−露光反復時における表
面電位や残留電位の上昇を抑制する効果が特に抜群であ
り、加えて、良好なりエンチング効果のため、紫外光に
対する感光体の耐光性をも向上させることができる。こ
れはジフェノキノン誘導体が有する特定の化学構造、即
ち共役結合構造に関連しているものと認められる。In addition, the diphenoquinone derivative used in the present invention is particularly effective among various electron-accepting substances in suppressing increases in surface potential and residual potential during repeated charging and exposure. Therefore, the light resistance of the photoreceptor to ultraviolet light can also be improved. This is recognized to be related to a specific chemical structure, ie, a conjugated bond structure, possessed by the diphenoquinone derivative.
本発明で用いるジフェノキノン誘導体は、種々の正孔輸
送物質への相溶性に優れており、またそれ自体高い電子
輸送能力を有することから、正孔輸送物質層中の電荷の
蓄積を防止するといる好都合な作用をもたらす。The diphenoquinone derivative used in the present invention has excellent compatibility with various hole-transporting substances, and also has high electron-transporting ability itself, so it has the advantage of preventing charge accumulation in the hole-transporting substance layer. It brings about a positive effect.
更に、上記組成物を単層分散型で使用した場合、正孔、
電子両方で電荷輸送されるため、感度が向上し、電荷発
生剤の含有量も少量でよいという利点も奏される。Furthermore, when the above composition is used in a monolayer dispersed form, holes,
Since charges are transported by both electrons, the sensitivity is improved and the charge generating agent content can be small.
［好適態様］
本発明は、積層型の電子写真用感光体や単層分散型の電
子写真感光体に適用することができる。[Preferred Embodiment] The present invention can be applied to a laminated type electrophotographic photoreceptor or a single-layer dispersion type electrophotographic photoreceptor.
例えば、第２図に示すように、導電性基板１上に電荷発
生層（ＣＧＬ）２を形成し、この電荷発生層上に前記正
孔輸送物質とジフェノキノン誘導体との組成物からなる
電荷輸送層（ＣＴＬ）３を設けることができる。For example, as shown in FIG. 2, a charge generation layer (CGL) 2 is formed on a conductive substrate 1, and a charge transport layer made of a composition of the hole transport substance and a diphenoquinone derivative is formed on the charge generation layer. (CTL)3 can be provided.
正帯電の場合（第２図Ａ） 、ＣＧＬ２で発生する正孔
Φ及び電子ｅの対の内、電子ｅがＣＴＬ３に注入され、
ＣＴＬ中のジフェノキノン誘導体による電子輸送により
静電像の形成が行われる。また負帯電の場合（第２図Ｂ
） 、ＣＧＬ２で発生する正孔ΦがＣＴＬ３に注入され
、ＣＴＬ中の正孔輸送物質による正孔輸送により静電像
の形成が行われる。In the case of positive charging (Figure 2A), of the pair of hole Φ and electron e generated in CGL2, electron e is injected into CTL3,
Electrostatic image formation occurs through electron transport by the diphenoquinone derivative in the CTL. In addition, in the case of negative charging (Fig. 2B
), holes Φ generated in CGL2 are injected into CTL3, and an electrostatic image is formed by hole transport by a hole transport substance in CTL.
或いは逆に、第３図に示すように、導電性基板１上に、
前記正孔輸送物質とジフェノキノン誘導体との組成物か
ら成る電荷輸送層３を設け、この電荷輸送層上に電荷発
生層２を設けることもできる。正帯電の場合（第３図Ａ
） 、ＣＧＬ２で発生する正孔Φ及び電子ｅの対の内、
正孔ΦがＣＴＬ３に注入され、ＣＴＬ中の正孔輸送物質
による正孔輸送により通電が行われて、静電像の形成が
行われる。負帯電の場合（第３図Ｂ）、逆にＣＧＬで発
生する電子ｅがＣＴＬ３に注入され、ＣＴＬ中のジフェ
ノキノン誘導体による電子輸送により、静電像の形成が
行われる。Or, conversely, as shown in FIG. 3, on the conductive substrate 1,
It is also possible to provide a charge transport layer 3 made of a composition of the hole transport substance and a diphenoquinone derivative, and to provide a charge generation layer 2 on this charge transport layer. In the case of positive charging (Fig. 3A)
), among the pairs of hole Φ and electron e generated in CGL2,
Holes Φ are injected into the CTL 3, and current is supplied through hole transport by a hole transport substance in the CTL, thereby forming an electrostatic image. In the case of negative charging (FIG. 3B), conversely, electrons e generated in the CGL are injected into the CTL 3, and an electrostatic image is formed by electron transport by the diphenoquinone derivative in the CTL.
更に、第４図に示す通り、導電性基板１上に、正孔輸送
物質とジフェノキノン誘導体との電荷輸送媒質中に電荷
発生物質を分散させたものを、感光層４として単層に設
けることができ、この場合には、正帯電に対しては（第
４図Ａ）、電荷発生物質で発生する正孔Φ及び電子ｅの
対の内、正孔輸送物質が導電性基板１側への正孔Φの輸
送を担当し、ジフェノキノン誘導体が表面側への電子ｅ
の輸送を担当し静電潜像の形成が行われる。逆に負帯電
に対しては（第４図Ｂ）ジフェノキノン誘導体が導電性
基板ｌ側への電子ｅの輸送を担当し、正孔輸送物質が表
面側への正孔Φの輸送を担当し静電潜像の形成が行われ
る。Furthermore, as shown in FIG. 4, it is possible to provide a single layer on the conductive substrate 1 as a photosensitive layer 4, in which a charge generating substance is dispersed in a charge transporting medium of a hole transporting substance and a diphenoquinone derivative. In this case, for positive charging (Fig. 4A), among the pairs of holes Φ and electrons e generated in the charge-generating substance, the hole-transporting substance transports the positive towards the conductive substrate 1 side. Responsible for the transport of pores Φ, the diphenoquinone derivative transports electrons e to the surface side.
It is responsible for the transport of electrostatic latent images and the formation of electrostatic latent images. Conversely, for negative charging (Fig. 4B), the diphenoquinone derivative is responsible for transporting electrons e to the conductive substrate l side, and the hole transport substance is responsible for transporting holes Φ to the surface side, resulting in static Formation of an electrolatent image takes place.
すなわち単層型感光体とした場合、感光層４中で発生し
た全ての電荷を効率よく輸送することができ、感度の向
上につながる。That is, in the case of a single-layer type photoreceptor, all the charges generated in the photosensitive layer 4 can be efficiently transported, leading to improved sensitivity.
本発明に用いるジフェノキノン誘導体としては、下記一
般式
式中、Ｒ＋、Ｒｓ、Ｒｓ及びＲ４の各々は水素原子、ア
ルキル基、シリロアルキル基、アリール基、アラルキル
基等である、
で表わされるものが好適に使用される。その適当な例は
、これに限定されないが、２．６−シメチルー２°、６
°−ジｔ−ブチルジフェノキノン、２．２°−ジメチル
−６，６°−ジｔ−ブチルジフェノキノン、２，６°−
ジメチル−２°、６°−ジｔ−ブチルジフェノキノン、
２，６．２’、６°−テトラメチルジフェノキノン、２
，６，２°、６°−テトラｔ−ブチルジフェノキノン、
２．６．２°、６°−テトラフエニルジフェノキノン、
２，６．２’、６’−テトラシクロへキシルジフェノキ
ノン、等を挙げることができるが、下記式［Ｉ］あるい
は式［１１］の関係を満足させる置換基を有したジフェ
ノキノン誘導体は、分子の対称性が低いために分子間の
相互作用が小さく、溶解性に優れているために好ましい
。Preferred diphenoquinone derivatives used in the present invention are those represented by the following general formula, in which each of R+, Rs, Rs, and R4 is a hydrogen atom, an alkyl group, a silyloalkyl group, an aryl group, an aralkyl group, etc. used. Suitable examples thereof include, but are not limited to, 2,6-dimethyl-2°,6
°-di-t-butyldiphenoquinone, 2.2°-dimethyl-6,6°-di-t-butyldiphenoquinone, 2,6°-
dimethyl-2°,6°-dit-butyldiphenoquinone,
2,6.2',6°-tetramethyldiphenoquinone, 2
,6,2°,6°-tetra-t-butyldiphenoquinone,
2.6.2°, 6°-tetraphenyldiphenoquinone,
2,6.2',6'-tetracyclohexyldiphenoquinone, etc., but diphenoquinone derivatives having a substituent satisfying the relationship of the following formula [I] or formula [11] are It is preferable because its low symmetry results in small intermolecular interactions and excellent solubility.
（Ｒ，の炭素数＝Ｒ鵞の炭素数）〉
（Ｒ，の炭素数＝Ｒ４の炭素数）・・・［Ｉ］（Ｒ１の
炭素数＝Ｒａの炭素数）〉
（Ｒ，の炭素数＝Ｒ，の炭素数）・・・［ＩＩ］正孔輸
送物質としては、低分子量の正孔輸送物質や高分子量の
正孔輸送物質が使用され、低分子量の正孔輸送物質は、
後述するバインダーとの組合せで使用される。かかる正
孔輸送物質としては、例えば、２，５−ジ（４−メチル
アミノフェニル） 、 ！、３．４−オキサジアゾール
、等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、有機
ポリシラン化合物、１−フェニル−３−（ｐ−ジメチル
アミノフェニル）ピラゾリン等のピラゾリン化合物、ヒ
ドラゾン化合物、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。(Number of carbon atoms in R = number of carbon atoms in R)〉 (Number of carbon atoms in R = number of carbon atoms in R4) ... [I] (Number of carbon atoms in R1 = number of carbon atoms in Ra)〉 (Number of carbon atoms in R = number of carbon atoms in R)... [II] As the hole transport substance, a low molecular weight hole transport substance or a high molecular weight hole transport substance is used, and the low molecular weight hole transport substance is
It is used in combination with the binder described below. Such hole transport substances include, for example, 2,5-di(4-methylaminophenyl), ! , oxadiazole compounds such as 3.4-oxadiazole, styryl compounds such as 9-(4-diethylaminostyryl)anthracene, carbazole compounds such as polyvinylcarbazole, organic polysilane compounds, 1-phenyl-3-( Pyrazoline compounds such as p-dimethylaminophenyl) pyrazoline, hydrazone compounds, triphenylamine compounds, indole compounds, oxazole compounds, isoxazole compounds, thiazole compounds, thiadiazole compounds, imidazole compounds, pyrazole compounds, Examples include nitrogen-containing cyclic compounds such as triazole compounds and fused polycyclic compounds.
高分子量の正孔輸送物質としてポリシランを用いること
もできる。このポリシランは、それ自体公知の任意のも
のであってよいが、主鎖がケイ素の連鎖から成り、側鎖
に有機基、特に−偏度化水素基を有するものであり、下
記式
式中、Ｒ８及びＲ２の各々は一価炭化水素基、特に、炭
素数４以下のアルキル基、炭素数６以上のアリール基、
アラルキル基を表わす、で示される反復単位から成る。Polysilane can also be used as a high molecular weight hole transport material. This polysilane may be of any type known per se, but the main chain consists of a silicon chain, and the side chain has an organic group, especially a polarized hydrogen group, and in the following formula: Each of R8 and R2 is a monovalent hydrocarbon group, particularly an alkyl group having 4 or less carbon atoms, an aryl group having 6 or more carbon atoms,
It represents an aralkyl group and consists of repeating units shown as.
好適な有機ポリシランは、メチルフェニルポリシラン、
メチルプロピルポリシラン、メチルｔ−ブチルポリシラ
ン、ジフェニルポリシラン、メチルトリルポリシラン或
いはこれらのコポリマー等である。Suitable organopolysilanes include methylphenylpolysilane,
Examples include methylpropylpolysilane, methyl t-butylpolysilane, diphenylpolysilane, methyltolylpolysilane, and copolymers thereof.
用いる有機ポリシランは、所謂フィルムを形成するに足
る分子量を有するべきであり、一般に５０００乃至５０
０００ 、特に５０００乃至２００００の重量平均分子
量（Ｍ、）を有することが好ましい。The organic polysilane used should have a molecular weight sufficient to form a so-called film, and generally has a molecular weight of 5,000 to 50
000, particularly preferably from 5,000 to 20,000.
有機ポリシランの末端は、シラノール基、アルコキシ基
等であってよい。The terminal end of the organic polysilane may be a silanol group, an alkoxy group, or the like.
本発明において、正孔輸送物質とジフェノキノン誘導体
とは、前述した量比で使用されるべきである。In the present invention, the hole transport substance and the diphenoquinone derivative should be used in the above-mentioned quantitative ratio.
電荷発生材料としては、例えば、セレン、セレン−テル
ル、アモルファスシリコン、ビリリウム塩、アゾ系顔料
、ジスアゾ系顔料、アンサンスロン系顔料、フタロシア
ニン系顔料、インジゴ系顔料、スレン系顔料、トルイジ
ン系顔料、ピラゾリン系顔料、ペリレン系顔料、キナク
リドン系顔料等が例示され、所望の領域に吸収波長域を
有するよう、一種または二種以上混合して用いられる。Examples of charge-generating materials include selenium, selenium-tellurium, amorphous silicon, biryllium salts, azo pigments, disazo pigments, anthanthrone pigments, phthalocyanine pigments, indigo pigments, threne pigments, toluidine pigments, and pyrazoline. Examples include pigments based on pigments, perylene pigments, and quinacridone pigments, which may be used singly or in combination of two or more so as to have an absorption wavelength range in a desired region.
この電荷発生材料は、蒸着等の手段で層の形に施すこと
もできるし、また結着樹脂に分散させた形で層として施
すこともできる。このような結着樹脂としては、種々の
樹脂が使用でき、例えば、スチレン系重合体、アクリル
系重合体、スチレン−アクリル系共重合体、エチレン−
酢酸ビニル共重合体、ポリプロピレン、アイオノマー等
のオレフィン系重合体、ポリ塩化ビニル、塩化ビニル−
酢酸ビニル共重合体、ポリエステル、アルキッド樹脂、
ポリアミド、ポリウレタン、エポキシ樹脂、ポリカーボ
ネート、ボリアリレート、ポリスルホン、ジアリルフタ
レート樹脂、シリコーン樹脂、ケトン樹脂、ポリビニル
ブチラール樹脂、ポリエーテル樹脂、フェノール樹脂や
、エポキシアクリレート等の光硬化型樹脂等各種の重合
体が例示できる。これらの結着樹脂は、一種または二種
以上混合して用いることもできる。This charge generating material can be applied in the form of a layer by means such as vapor deposition, or can be applied as a layer in the form of being dispersed in a binder resin. Various resins can be used as such binder resins, such as styrene polymers, acrylic polymers, styrene-acrylic copolymers, and ethylene-acrylic copolymers.
Vinyl acetate copolymers, polypropylene, olefin polymers such as ionomers, polyvinyl chloride, vinyl chloride
Vinyl acetate copolymer, polyester, alkyd resin,
Various polymers such as polyamide, polyurethane, epoxy resin, polycarbonate, polyarylate, polysulfone, diallyl phthalate resin, silicone resin, ketone resin, polyvinyl butyral resin, polyether resin, phenol resin, and photocurable resin such as epoxy acrylate are used. I can give an example. These binder resins may be used alone or in combination of two or more.
また、塗布液を形成するのに使用する溶剤としては、種
々の有機溶剤が使用でき、メタノール、エタノール、イ
ソプロパツール、ブタノール等のアルコール類、ｎ−ヘ
キンサン、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、ジメチルホルムアミド、ジ
メチルスルホキシド等、種々の溶剤が例示され、一種ま
たは二種以上混合して用いられる。In addition, various organic solvents can be used as the solvent used to form the coating solution, including alcohols such as methanol, ethanol, isopropanol, and butanol, and carbonized aliphatic solvents such as n-hexane, octane, and cyclohexane. Hydrogen, aromatic hydrocarbons such as benzene, toluene, xylene, halogenated hydrocarbons such as dichloromethane, dichloroethane, carbon tetrachloride, chlorobenzene, ethers such as dimethyl ether, diethyl ether, tetrahydrofuran, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, acetone, Ketones such as methyl ethyl ketone and cyclohexane, ethyl acetate,
Various solvents are exemplified, such as esters such as methyl acetate, dimethylformamide, and dimethyl sulfoxide, which may be used alone or in combination of two or more.
導電性基板としては、導電性を有する種々の材料が使用
でき、例えば、アルミニウム、銅、錫、白金、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、インジウム、ステンレス鋼、真鍮の金属単
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、酸化錫、酸化インジウ
ム等で被覆されたガラス等が例示される。Various conductive materials can be used as the conductive substrate, such as aluminum, copper, tin, platinum, gold, silver,
Single metals such as vanadium, molybdenum, chromium, cadmium, titanium, nickel, indium, stainless steel, and brass, plastic materials on which the above metals are vapor-deposited or laminated, glass coated with aluminum iodide, tin oxide, indium oxide, etc. is exemplified.
尚、塗布液を形成するには、電荷発生材料等と結着樹脂
等を、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、ペイントシェイカーあるいは超音波分
散器等を用いて調整し、従来公知の塗布手段により塗布
、乾燥すればよい。In order to form the coating liquid, the charge-generating material and the binder resin are adjusted using a conventionally known method such as a roll mill, a ball mill, an attritor, a paint shaker, or an ultrasonic disperser. It may be applied and dried using the following application means.
第２図の基板／ＣＧ Ｌ／ＣＴ Ｌ感光体の場合、ＣＧ
Ｌは、蒸着の場合の０．Ｏｌ乃至０．０５μｍから塗布
の場合の０．Ｏｌ乃至０．０５μｍ迄変化するが、ＣＴ
Ｌは５乃至４０μｖａ、特に１０乃至２５μｍの範囲に
あるのがよい、第３図の基板／ＣＴＬ／ＣＧＬ感光体の
場合、ＣＴＬは５乃至４０ＩＬｍ、特に１０乃至２５μ
ｍの厚みを有し、一方ＣＧＬは０．１乃至０．５μｍの
厚みを有するのがよい。また、第４図のＣＴＭ及びＣＧ
Ｍ分散型感光体では、電荷発生材料は感光層中に有機ポ
リシラン１００重量部に対して１乃至１５重量部、特に
５乃至１０重量部の量で存在するのがよく、感光層は１
０乃至４０μ諷、特に１５乃至３０μｍの厚みを有する
のが好ましい。In the case of the substrate/CG L/CT L photoconductor in Figure 2, CG
L is 0.0 in the case of vapor deposition. 0.05 μm for coating from Ol to 0.05 μm. It varies from Ol to 0.05μm, but CT
L is preferably in the range of 5 to 40 μva, especially 10 to 25 μm. In the case of the substrate/CTL/CGL photoreceptor of FIG. 3, CTL is in the range of 5 to 40 ILm, especially 10 to 25 μm.
The CGL preferably has a thickness of 0.1 to 0.5 μm, while the CGL has a thickness of 0.1 to 0.5 μm. In addition, CTM and CG in Fig. 4
In the M dispersion type photoreceptor, the charge generating material is preferably present in the photosensitive layer in an amount of 1 to 15 parts by weight, particularly 5 to 10 parts by weight, based on 100 parts by weight of the organic polysilane;
It is preferable to have a thickness of 0 to 40 μm, particularly 15 to 30 μm.
［発明の効果］
本発明によれば、電荷発生物質と電荷輸送物質との組合
せを用いる感光体において電荷輸送物質として正孔輸送
物質と特定量のジフェノキノン誘導体との組合せを用い
ることにより、正と負との両帯電で動作する感光体を提
供することが可能となった。[Effects of the Invention] According to the present invention, positive and It has become possible to provide a photoreceptor that operates with both negative and negative charges.
また、電荷の蓄積がなくなり、繰り返し使用時の安定性
及び耐刷性が向上した。更に、電荷輸送物質中のジフェ
ノキノン誘導体がクエンチャ−として働き、耐光性が向
上した。また、単層型感光体とした場合、電荷発生顔料
の含有量が少量でよくなり、しかも高感度が得られるよ
うになった。In addition, there was no charge accumulation, and stability and printing durability during repeated use were improved. Furthermore, the diphenoquinone derivative in the charge transport material acts as a quencher, improving light resistance. Furthermore, when a single-layer type photoreceptor is used, a small amount of charge-generating pigment is required, and high sensitivity can be obtained.
［実施例］
以下に、実施例の基づき、本発明をより詳細に説明する
。[Examples] The present invention will be described in more detail below based on Examples.
（実施例１）
電荷発生物質としてのα型オキソチタニルフタロシアニ
ン１００重量部、溶媒としてのテトラヒドロフラン４０
００重量部をボールミルに仕込、２４時間攪拌した後、
結着樹脂としてポリビニルブチラール（種水化学社製、
商品名工スレツクＢＭ−３）１００重量部を加え更に１
時間攪拌混合して電荷発生層用塗布液を調整し、この調
整液をアルミニウム箔上にワイヤーバー（Ｎｏ、５）に
て塗布した後、１００℃で３０分間熱風乾燥して硬化さ
せることにより膜厚的０．５μ朧の電荷発生層を形成し
た。(Example 1) 100 parts by weight of α-type oxotitanylphthalocyanine as a charge generating substance, 40 parts by weight of tetrahydrofuran as a solvent
After charging 00 parts by weight into a ball mill and stirring for 24 hours,
Polyvinyl butyral (manufactured by Tanezu Kagaku Co., Ltd.,
Add 100 parts by weight of product name Kosuretsuku BM-3) and further 1
A coating solution for the charge generation layer was prepared by stirring and mixing for a period of time, and this solution was applied onto an aluminum foil using a wire bar (No. 5), and then dried with hot air at 100°C for 30 minutes to harden the coating solution. A charge generation layer having a thickness of 0.5 μm was formed.
次に、正孔輸送物質としてのＮ、Ｎ、Ｎ’、Ｎ’−テト
ラキス（３−トリル）−１，３−フェニレンジアミン３
０重量部、ジフェノキノン誘導体としての２．６−シメ
チルー２°、６゛−ジｔｅｒｔ−ジブチルジフェノキノ
ン７０重量部、結着樹脂としてのポリカーボネート（三
菱瓦斯化学社製、商品名２２００）ｉｏｏ重量部及び溶
媒としてのテトラヒドロフラン９００重量部をホモミキ
サーで攪拌混合して電荷輸送層用塗布液を調整した。Next, N,N,N',N'-tetrakis(3-tolyl)-1,3-phenylenediamine 3 as a hole transport material
0 parts by weight, 70 parts by weight of 2,6-dimethyl-2°,6゛-di-tert-dibutyldiphenoquinone as a diphenoquinone derivative, ioo parts by weight of polycarbonate (manufactured by Mitsubishi Gas Chemical Co., Ltd., trade name 2200) as a binder resin and 900 parts by weight of tetrahydrofuran as a solvent were stirred and mixed using a homomixer to prepare a charge transport layer coating solution.
この塗布液を上記電荷発生層上にワイヤーバー（Ｎｏ、
６０）にて塗布した後、１００℃で３０分間熱風乾燥す
ることにより膜厚的１５μｍで電荷輸送層を形成し、積
層型電子写真用感光体を作製した。Apply this coating solution onto the charge generation layer with a wire bar (No.
60) and then dried with hot air at 100° C. for 30 minutes to form a charge transport layer with a thickness of 15 μm, thereby producing a laminated electrophotographic photoreceptor.
（実施例２）
電荷輸送層用塗布液の調整において、正孔輸送物質とし
てのＮ、Ｎ、Ｎ’、Ｎ’−テトラキス（３−トリル）−
１，３−フェニレンジアミンを４０重量部、ジフェノキ
ノン誘導体としての２．６−シメチルー２°、６′−ジ
ｔｅｒｔ−ジブチルジフェツキノンを６０重量部用いた
こと以外は、実施例１と同様にして積層型電子写真感光
体を作製した。(Example 2) In the preparation of a coating solution for a charge transport layer, N, N, N', N'-tetrakis(3-tolyl)- as a hole transport substance
The same procedure as in Example 1 was carried out, except that 40 parts by weight of 1,3-phenylenediamine and 60 parts by weight of 2,6-dimethyl-2°,6'-di-tert-dibutyldifetuquinone as a diphenoquinone derivative were used. A laminated electrophotographic photoreceptor was produced.
（実施例３）
電荷輸送層用塗布液の調整において、正孔輸送物質とし
てのＮ、Ｎ、Ｎ’、Ｎ’−テトラキス（３−トリル）−
１，３−フェニレンジアミンを６０重量部、ジフェノキ
ノン誘導体としての２，６−シメチルー２’ 、６’
−ジｔｅｒｔ−ジブチルジフェノキノンを４０重量部用
いたこと以外は、実施例１と同様にして積層型電子写真
感光体を作製した。(Example 3) In preparing a coating solution for a charge transport layer, N, N, N', N'-tetrakis(3-tolyl)- was used as a hole transport substance.
60 parts by weight of 1,3-phenylenediamine, 2,6-dimethyl-2',6' as a diphenoquinone derivative
A laminated electrophotographic photoreceptor was produced in the same manner as in Example 1, except that 40 parts by weight of -di-tert-dibutyldiphenoquinone was used.
（実施例４）
電荷輸送層用塗布液の調整において、正孔輸送物質とし
てのＮ、Ｎ、Ｎ’、Ｎ’−テトラキス（３−トリル）−
１，３−フェニレンジアミンを６０重量部、ジフェノキ
ノン誘導体としての２，６−シメチルー２° ６°−ジ
ｔｅｒｔ−ジブチルジフェノキノンを８０重量部用いた
こと以外は、実施例１と同様にして積層型電子写真感光
体を作製した。(Example 4) In preparing the coating solution for the charge transport layer, N, N, N', N'-tetrakis(3-tolyl)- was used as the hole transport substance.
Lamination was carried out in the same manner as in Example 1, except that 60 parts by weight of 1,3-phenylenediamine and 80 parts by weight of 2,6-dimethyl-2°6°-di-tert-dibutyldiphenoquinone as a diphenoquinone derivative were used. A type electrophotographic photoreceptor was manufactured.
（実施例５）
電荷輸送層用塗布液の調整において、正孔輸送物質とし
てのＮ、Ｎ、Ｎ’、Ｎ’−テトラキス（３−トリル）−
１，３−フェニレンジアミンを８０重量部、ジフェノキ
ノン誘導体としての２，６−シメチルー２°、６°−ジ
ｔ ｅ’ ｒ ｔ−ジブチルジフェノキノンを６０重量
部用いたこと以外は、実施例１と同様にして積層型電子
写真感光体を作製した。(Example 5) In preparing the coating solution for the charge transport layer, N, N, N', N'-tetrakis(3-tolyl)- was used as the hole transport substance.
Example 1 except that 80 parts by weight of 1,3-phenylenediamine and 60 parts by weight of 2,6-dimethyl-2°,6°-dibutyldiphenoquinone as a diphenoquinone derivative were used. A laminated electrophotographic photoreceptor was produced in the same manner as described above.
（実施例６）
電荷輸送層用塗布液の調整において、正孔輸送物質とし
てのＮ、Ｎ、Ｎ’、Ｎ’−テトラキス（３−トリル）−
１，３−フェニレンジアミンを１７０重量部、ジフェノ
キノン誘導体としての２．６−シメチルー２°、６°−
ジｔａｒｔ−ジブチルジフェノキノンを５０重量部用い
たこと以外は、実施例１と同様にして積層型電子写真感
光体を作製した。(Example 6) In preparing the coating solution for the charge transport layer, N, N, N', N'-tetrakis(3-tolyl)-
170 parts by weight of 1,3-phenylenediamine, 2,6-dimethyl-2°, 6°- as a diphenoquinone derivative
A laminated electrophotographic photoreceptor was produced in the same manner as in Example 1 except that 50 parts by weight of ditart-dibutyldiphenoquinone was used.
（比較例１）
電荷輸送層用塗布液の調整において、正孔輸送物質とし
てのＮ、Ｎ、Ｎ’、Ｎ’−テトラキス（３−トリＪＬ、
） −１，３−フェニレンジアミンを１００１ｉ量部用
い、ジフェノキノン誘導体としての２，６−シメチルー
２°、６°−ジｔｅｒｔ−ジブチルジフェノキノンを用
いなかったこと以外は、実施例１と同様にして積層型電
子写真感光体を作製した。(Comparative Example 1) In preparing the coating solution for the charge transport layer, N,N,N',N'-tetrakis (3-triJL,
) The same procedure as in Example 1 was carried out, except that 1001 parts of -1,3-phenylenediamine was used and 2,6-dimethyl-2°,6°-di-tert-dibutyldiphenoquinone was not used as the diphenoquinone derivative. A laminated electrophotographic photoreceptor was produced.
（比較例２）
電荷輸送層用塗布液の調整において、正孔輸送物質とし
てのＮ、Ｎ、Ｎ’、Ｎ’−テトラキス（３−トリル）−
１，３−フェニレンジアミンを用いず、ジフェノキノン
誘導体としての２，６−シメチルー２° ６°−ジｔ
ｅｒｔ−ジブチルジフェノキノンを１００重量部用いる
こと以外は、実施例１と同様にして積層型電子写真感光
体を作製した。(Comparative Example 2) In the preparation of a coating solution for a charge transport layer, N, N, N', N'-tetrakis(3-tolyl)-
2,6-dimethyl-2°6°-dit as a diphenoquinone derivative without using 1,3-phenylenediamine
A laminated electrophotographic photoreceptor was produced in the same manner as in Example 1 except that 100 parts by weight of ert-dibutyldiphenoquinone was used.
（比較例３）
電荷輸送層用塗布液の調整において、正孔輸送物質とし
てのＮ、Ｎ、Ｎ’、Ｎ’−テトラキス（３−トリル）−
１，３−フェニレンジアミンを８０重量部、ジフェノキ
ノン誘導体としての２．６−シメチルー２°、６°−ジ
ｔｅｒｔ−ジブチルジフェノキノンを２０重量部用いた
こと以外は、実施例１と同様にして積層型電子写真感光
体を作製した。(Comparative Example 3) In the preparation of a coating solution for a charge transport layer, N, N, N', N'-tetrakis(3-tolyl)-
The same procedure as in Example 1 was carried out, except that 80 parts by weight of 1,3-phenylenediamine and 20 parts by weight of 2,6-dimethyl-2°,6°-di-tert-dibutyldiphenoquinone as a diphenoquinone derivative were used. A laminated electrophotographic photoreceptor was manufactured.
（比較例７）
電荷発生物質としてのＸ型メタルフリーフタロシアニン
０．５重量部、正孔輸送物質としてのＮ、 Ｎ。(Comparative Example 7) 0.5 parts by weight of X-type metal-free phthalocyanine as a charge-generating substance, and N as a hole-transporting substance.
Ｎ’、Ｎ’−テトラキス（３−トリル）−１，３−フェ
ニレンジアミン６０重量部、ジフェノキノン誘導体とし
ての２．６−シメチルー２°、６゜ジｔｅｒｔ−ジブチ
ルジフェノキノン８０重量部、結着樹脂としてのポリカ
ーボネート（三菱瓦斯化学社製、商品名２２００）１０
０重量部及び溶媒としてのテトラヒドロフラン９００重
量部を、超音波分散器で混合分散して単層型感光層用塗
布液を調整し、この調整液をアルミニウム箔上にワイヤ
ーバー（Ｎｏ、６０）にて塗布した後、１００℃で３０
分間熱風乾燥することにより膜厚約１５μ麿の単層型電
子写真用感光体を作製した。60 parts by weight of N',N'-tetrakis(3-tolyl)-1,3-phenylenediamine, 80 parts by weight of 2,6-dimethyl-2°,6° di-tert-dibutyldiphenoquinone as a diphenoquinone derivative, binding Polycarbonate as resin (manufactured by Mitsubishi Gas Chemical Co., Ltd., trade name 2200) 10
0 parts by weight and 900 parts by weight of tetrahydrofuran as a solvent were mixed and dispersed using an ultrasonic disperser to prepare a coating solution for a single layer type photosensitive layer, and this prepared solution was spread on a wire bar (No. 60) on an aluminum foil. After coating, apply at 100℃ for 30 minutes.
A single-layer electrophotographic photoreceptor having a film thickness of about 15 μm was prepared by drying with hot air for minutes.
（比較例４）
正孔輸送物質としてのＮ、Ｎ、Ｎ’、Ｎ’−テトラキス
（３−）ＩＪ７１ｚ） −１，３−フェニレンジアミン
を１００重量部用い、ジフェノキノン誘導体としての２
，６−シメチルー２゛、６°−ジｔｅｒｔ−ジブチルジ
フェノキノンを用いなかったこと以外は、実施例７と同
様にして単層型電子写真感光体を作製した。(Comparative Example 4) Using 100 parts by weight of N,N,N',N'-tetrakis(3-)IJ71z)-1,3-phenylenediamine as a hole transport substance, 2 as a diphenoquinone derivative
A single-layer electrophotographic photoreceptor was prepared in the same manner as in Example 7, except that ,6-dimethyl-2',6'-di-tert-dibutyldiphenoquinone was not used.
（比較例５）
正孔輸送物質としてのＮ、Ｎ、Ｎ’、Ｎ’−テトラキス
（３−トリル）−１，３−フェニレンジアミンを用いず
、ジフェノキノン誘導体としての２，６−シメチルー２
°、６゛−ジｔｅｒｔ−ジブチルジフェノキノンを１０
０重量部用いること以外は、実施例７と同様にして単層
型電子写真感光体を作製した。(Comparative Example 5) Using 2,6-dimethyl-2 as a diphenoquinone derivative without using N,N,N',N'-tetrakis(3-tolyl)-1,3-phenylenediamine as a hole transport substance.
°, 6゛-di-tert-dibutyldiphenoquinone 10
A single-layer electrophotographic photoreceptor was produced in the same manner as in Example 7 except that 0 part by weight was used.
（実施例８）
［フェニルメチルポリシランの合成］
メチルフエニルジクロロシラン１００ｇ、金１ｉナトリ
ウム２６ｇを乾燥トルエン４００ｍ１に加え１３０℃に
加熱し、１１時間攪拌した後冷却する、得られた反応液
（濃紫色を含む溶液）にエタノールを加え未反応のナト
リウムをエトキシドにした後、沈澱を濾別し乾燥後、ト
ルエンに溶かしてエタノール中に滴下再沈澱させて白色
のフェニルメチルポリシランを得た（収量２２．０ｇ
：収率３４％）。(Example 8) [Synthesis of phenylmethylpolysilane] 100 g of methylphenyldichlorosilane and 26 g of sodium gold 1i were added to 400 ml of dry toluene, heated to 130°C, stirred for 11 hours, and then cooled. After adding ethanol to the solution (containing purple color) to convert unreacted sodium into ethoxide, the precipitate was filtered off, dried, dissolved in toluene, and reprecipitated dropwise into ethanol to obtain white phenylmethylpolysilane (yield: 22 .0g
: yield 34%).
［電子写真感光体の調整］
電荷発生物質としてのＸ型メタルフリーフタロシアニン
０．５重量部、正孔輸送物質としてのフェニルメチルポ
リシラン１００重量部、ジフェノキノン誘導体としての
２．６−シメチルー２゛ ６゛−ジｔｅｒｔ−ジブチ
ルジフェノキノン１００重量部及び溶媒としてのテトラ
ヒドロフラン１０００重量部を、超音波分散器で混合分
散して単層型感光層用塗布液を調整し、この塗布液をア
ルミニウム箔上にワイヤーバー（Ｎｏ、６０）にて塗布
した後、１００℃で３０分間熱風乾燥することにより膜
厚約１０μ重で単層型電子写真用感光体を作製した。[Preparation of electrophotographic photoreceptor] 0.5 parts by weight of X-type metal-free phthalocyanine as a charge-generating substance, 100 parts by weight of phenylmethylpolysilane as a hole-transporting substance, and 2,6-dimethyl-2゛6゛ as a diphenoquinone derivative. -100 parts by weight of di-tert-dibutyldiphenoquinone and 1000 parts by weight of tetrahydrofuran as a solvent are mixed and dispersed using an ultrasonic disperser to prepare a coating solution for a single layer type photosensitive layer, and this coating solution is spread on an aluminum foil. After coating with a wire bar (No. 60), the coating was dried with hot air at 100° C. for 30 minutes to prepare a single-layer electrophotographic photoreceptor with a film thickness of about 10 μm.
（比較例６）
ジフェノキノン誘導体としての２，６−シメチルー２°
６゛−ジｔｅｒｔ−ジブチルジフェノキノンを用い
なかったこと以外は、実施例８と同様にして単層型電子
写真感光体を作製した。(Comparative Example 6) 2,6-dimethyl-2° as a diphenoquinone derivative
A single-layer electrophotographic photoreceptor was produced in the same manner as in Example 8 except that 6'-di-tert-dibutyldiphenoquinone was not used.
の−
静電複写試験装置（川口電気社製、Ｍｏｄｅｌ−８１０
０）を用いて、各実施例で得られた感光体に印加電圧±
６．ＯＫＶで正あるいは負に帯電させ、下記の条件で電
子写真特性を測定し、その結果を表１乃至表３に示した
。- Electrostatic copying test device (manufactured by Kawaguchi Electric Co., Ltd., Model-810
0) to apply voltage ±
6. The samples were positively or negatively charged with OKV and their electrophotographic properties were measured under the following conditions, and the results are shown in Tables 1 to 3.
露光時間 ：１０秒
照射光 ニア８０ｎｍ単色光
露光強度 ； ０．１ｍＷ ／ ｃｔａ”なお、表中ｖ
１（ｖ）は上記条件で電圧を印加して、感光体を帯電さ
せた時の感光体の初期表面電位ｖ１（Ｖ）ヲ示し、また
Ｅ＋ １ ／ ２ （ｕ Ｊ ／ ｃｍ”）は表面電位
が当初の表面電位Ｖ、（Ｖ）の１／２になるのに要した
時間より算出した半減露光量を示す。また、表中のＶ、
、、（Ｖ）は露光開始後５秒経過後の表面電位を残留電
位として測定したものである。Exposure time: 10 seconds irradiation light Near 80 nm monochromatic light Exposure intensity: 0.1 mW / cta" Note that v in the table
1 (v) indicates the initial surface potential v1 (V) of the photoconductor when the photoconductor is charged by applying a voltage under the above conditions, and E+ 1/2 (u J / cm") is the surface potential Indicates the half-reduced exposure amount calculated from the time required for V to become 1/2 of the initial surface potential V, (V).
,, (V) is the surface potential measured 5 seconds after the start of exposure as a residual potential.
さらに、帯電−露光の繰り返しを１０００回行い、その
時の感光体の表面電位■２（■）、半減露光量Ｅ＊ｘ／
２（μＪ／ｃｍ”）、残留電位ｖｘｒｐｍを測定した。Furthermore, charging and exposure were repeated 1000 times, and the surface potential of the photoreceptor at that time ■2 (■), the half-reduced exposure amount E*x/
2 (μJ/cm”) and the residual potential vxrpm was measured.
一方、実施例５、比較例１で得られた感光体に紫外線（
３００〜４００ｎｍ、 ６００ｍＷ／ａｍ−”）を１０
分間照射した後の感光体の表面電位Ｖ、。（Ｖ）。On the other hand, the photoreceptors obtained in Example 5 and Comparative Example 1 were coated with ultraviolet light (
300-400nm, 600mW/am-”) to 10
Surface potential V of the photoreceptor after irradiation for minutes. (V).
半減露光量Ｅ１ｏ １／２ （μＪ／ｃｍ”）、残留電
位Ｖ。Half-reduced exposure amount E1o 1/2 (μJ/cm”), residual potential V.
ａｒｐを測定し、その結果を表４に示した。ARP was measured and the results are shown in Table 4.
上記表１乃至表３の結果により、電荷輸送物質が正孔輸
送物質１００重量部部当たり３０重量部よりも多い量の
ジフェノキノン誘導体を含有した実施例１乃至実施例８
の電子写真感光体は、何れも、良好な両帯電性を示すと
ともに、帯電−露光の繰り返しによっても表面電位、感
度および残留電位の変化量が小さく、優れた繰り返し特
性を有することが判明した。一方、比較例３および１よ
り明らかなようにジフェノキノン誘導体の量が少なくな
ると正帯電における感度や残留電位が悪化する傾向にあ
り、ジフェノキノン誘導体を含有しない場合は正帯電で
の光減衰さえ起こらなかった。また、比較例２より明ら
かなようにジフェノキノン誘導体だけを含有する場合は
負帯電における光減衰が起こらなかった。According to the results in Tables 1 to 3 above, Examples 1 to 8 in which the charge transport material contained more than 30 parts by weight of the diphenoquinone derivative per 100 parts by weight of the hole transport material.
It was found that all of the electrophotographic photoreceptors exhibited good bistatic charging properties, and showed small changes in surface potential, sensitivity, and residual potential even after repeated charging and exposure, and had excellent repeatability. On the other hand, as is clear from Comparative Examples 3 and 1, when the amount of the diphenoquinone derivative is reduced, the sensitivity and residual potential at positive charging tend to worsen, and when no diphenoquinone derivative is contained, even light attenuation at positive charging does not occur. . Further, as is clear from Comparative Example 2, when only the diphenoquinone derivative was contained, no light attenuation occurred during negative charging.
さらに、表４の結果によりジフェノキノン誘導体を含有
する実施例５の電子写真感光体は、紫外線の照射によっ
ても、表面電位および残留電位の変化量が小さく、優れ
た耐光性をも有することが判明した。Furthermore, the results in Table 4 show that the electrophotographic photoreceptor of Example 5 containing the diphenoquinone derivative showed small changes in surface potential and residual potential even when irradiated with ultraviolet rays, and also had excellent light resistance. .
第１図は、＠２図に示す構成の積層型電子写真感光体を
用いて、正孔輸送物質としてのテトラフェニルメタフェ
ニレンジアミン系化合物と、電子輸送物質としてのジフ
ェノキノン誘導体との配合比を変化させて、正帯電時及
び負ｉ！時の感度の逆数をプロットさせたものである。
第２図は、本発明の負帯電型感光体の断面図である。第
３図は、本発明の正帯電型感光体の断面図である。
第４図は、本発明の単層型感光体の断面図である。
１・・・導電性基板、２・・・電荷発生層、３・・・電
荷輸送層、４・・・単層型感光層Figure 1 shows the composition ratio of a tetraphenylmetaphenylenediamine compound as a hole transport substance and a diphenoquinone derivative as an electron transport substance using a laminated electrophotographic photoreceptor having the configuration shown in Figure 2. When charged positively and negatively i! This is a plot of the reciprocal of sensitivity over time. FIG. 2 is a sectional view of the negatively charged photoreceptor of the present invention. FIG. 3 is a sectional view of the positively charged photoreceptor of the present invention. FIG. 4 is a cross-sectional view of the single-layer photoreceptor of the present invention. DESCRIPTION OF SYMBOLS 1... Conductive substrate, 2... Charge generation layer, 3... Charge transport layer, 4... Single layer type photosensitive layer
Claims (1)
単層分散型で含有する電子写真用有機感光体において、
電荷輸送物質が正孔輸送物質１００重量部当り３０重量
部よりも多い量のジフェノキノン誘導体を含有する、組
成物から成ることを特徴とする両帯電可能な電子写真用
有機感光体。(1) In an electrophotographic organic photoreceptor containing a charge-generating substance and a charge-transporting substance in a layered form or a monolayer dispersed form,
1. A bi-chargeable electrophotographic organic photoreceptor, characterized in that the charge transport material comprises a composition containing a diphenoquinone derivative in an amount greater than 30 parts by weight per 100 parts by weight of the hole transport material.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2053827A JP2732697B2 (en) | 1990-03-07 | 1990-03-07 | Organic photoreceptor for electrophotography capable of both charging |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2053827A JP2732697B2 (en) | 1990-03-07 | 1990-03-07 | Organic photoreceptor for electrophotography capable of both charging |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH03256050A true JPH03256050A (en) | 1991-11-14 |
| JP2732697B2 JP2732697B2 (en) | 1998-03-30 |
Family
ID=12953630
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2053827A Expired - Lifetime JP2732697B2 (en) | 1990-03-07 | 1990-03-07 | Organic photoreceptor for electrophotography capable of both charging |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2732697B2 (en) |
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0506387A2 (en) * | 1991-03-26 | 1992-09-30 | Mita Industrial Co., Ltd. | Electrophotographic organic photosensitive material |
| US5274084A (en) * | 1991-11-27 | 1993-12-28 | Mita Industrial Co., Ltd. | Bisazo compounds which contain a diphenoquinone tetraazo component and an electrophotographic photosensitive member having a photosensitive layer comprising the bisazo compound |
| US5288576A (en) * | 1991-11-27 | 1994-02-22 | Mita Industrial Co., Ltd. | Electrophotographic member having an azo compound with diphenoquinone |
| JPH06130693A (en) * | 1992-10-09 | 1994-05-13 | Mita Ind Co Ltd | Electrophotographic sensitive body |
| US5336576A (en) * | 1991-11-27 | 1994-08-09 | Mita Industrial Co., Ltd. | Electrophotographic photosensitive member having a photosensitive layer comprising the azo compound |
| US6395440B1 (en) | 2000-03-21 | 2002-05-28 | Fuji Xerox Co., Ltd. | Electrophotographic photoreceptor, process cartridge and electrophotographic apparatus using the same |
| USRE39516E1 (en) | 1999-10-25 | 2007-03-13 | Kyocera Mita Corporation | Single-layer type electrophotosensitive material and image forming apparatus using the same |
| JP2012185419A (en) * | 2011-03-08 | 2012-09-27 | Ricoh Co Ltd | Electrophotographic photoreceptor and image forming method using the same, image forming apparatus and process cartridge for image forming apparatus |
| US9671705B2 (en) | 2013-07-16 | 2017-06-06 | Fuji Electric Co., Ltd. | Electrophotographic photoconductor, production method thereof, and electrophotographic apparatus |
| US9904186B2 (en) | 2011-08-05 | 2018-02-27 | Fuji Electric Co., Ltd. | Electrophotographic photoreceptor, method for manufacturing same, and electrophotographic apparatus using same |
| US10429752B2 (en) | 2017-02-24 | 2019-10-01 | Fuji Electric Co., Ltd. | Electrophotographic photoconductor, manufacturing method thereof, and electrophotographic apparatus using the same |
| US10962893B2 (en) | 2016-07-22 | 2021-03-30 | Fuji Electric Co., Ltd. | Photosensitive body for electrophotography, method for producing same and electrophotographic apparatus |
| US11036151B2 (en) | 2018-01-19 | 2021-06-15 | Fuji Electric Co., Ltd. | Electrophotographic photoreceptor, method for manufacturing same, and electrophotographic device |
| JP2021092632A (en) * | 2019-12-09 | 2021-06-17 | キヤノン株式会社 | Electrophotographic photoreceptor, process cartridge and electrophotographic device |
| US11143976B2 (en) | 2018-01-19 | 2021-10-12 | Fuji Electric Co., Ltd. | Photoconductor having interlayer for hole injection promotion |
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|---|---|---|---|---|
| US8110326B2 (en) | 2007-06-04 | 2012-02-07 | Ricoh Company Limited | Electrophotographic photoreceptor, image forming apparatus, and process cartridge |
| JP5386884B2 (en) | 2007-09-10 | 2014-01-15 | 株式会社リコー | Naphthalenetetracarboxylic acid diimide derivative and electrophotographic photoreceptor using the naphthalenetetracarboxylic acid diimide derivative |
| JP5403350B2 (en) | 2009-09-10 | 2014-01-29 | 株式会社リコー | Electrophotographic photosensitive member, electrophotographic method, electrophotographic apparatus, and process cartridge for electrophotographic apparatus |
| US8586270B2 (en) | 2011-03-30 | 2013-11-19 | Ricoh Company, Ltd. | Electrophotographic photoconductor, electrophotographic method, and electrophotographic apparatus |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5511545A (en) * | 1978-07-12 | 1980-01-26 | Ajinomoto Co Inc | Novel cyano-substituted diphenoxyquinone and its preparation |
| JPS63241548A (en) * | 1987-03-30 | 1988-10-06 | Fuji Xerox Co Ltd | Organic electronic material |
-
1990
- 1990-03-07 JP JP2053827A patent/JP2732697B2/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5511545A (en) * | 1978-07-12 | 1980-01-26 | Ajinomoto Co Inc | Novel cyano-substituted diphenoxyquinone and its preparation |
| JPS63241548A (en) * | 1987-03-30 | 1988-10-06 | Fuji Xerox Co Ltd | Organic electronic material |
Cited By (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0506387A2 (en) * | 1991-03-26 | 1992-09-30 | Mita Industrial Co., Ltd. | Electrophotographic organic photosensitive material |
| US5324610A (en) * | 1991-03-26 | 1994-06-28 | Mita Industrial Co., Ltd. | Electrophotographic organic photosensitive material with diphenoquinone derivative |
| US5274084A (en) * | 1991-11-27 | 1993-12-28 | Mita Industrial Co., Ltd. | Bisazo compounds which contain a diphenoquinone tetraazo component and an electrophotographic photosensitive member having a photosensitive layer comprising the bisazo compound |
| US5288576A (en) * | 1991-11-27 | 1994-02-22 | Mita Industrial Co., Ltd. | Electrophotographic member having an azo compound with diphenoquinone |
| US5336576A (en) * | 1991-11-27 | 1994-08-09 | Mita Industrial Co., Ltd. | Electrophotographic photosensitive member having a photosensitive layer comprising the azo compound |
| JPH06130693A (en) * | 1992-10-09 | 1994-05-13 | Mita Ind Co Ltd | Electrophotographic sensitive body |
| USRE42189E1 (en) | 1999-10-25 | 2011-03-01 | Kyocera Mita Corporation | Single-layer type electrophotosensitive material and image forming apparatus using the same |
| USRE39516E1 (en) | 1999-10-25 | 2007-03-13 | Kyocera Mita Corporation | Single-layer type electrophotosensitive material and image forming apparatus using the same |
| US6395440B1 (en) | 2000-03-21 | 2002-05-28 | Fuji Xerox Co., Ltd. | Electrophotographic photoreceptor, process cartridge and electrophotographic apparatus using the same |
| JP2012185419A (en) * | 2011-03-08 | 2012-09-27 | Ricoh Co Ltd | Electrophotographic photoreceptor and image forming method using the same, image forming apparatus and process cartridge for image forming apparatus |
| US9904186B2 (en) | 2011-08-05 | 2018-02-27 | Fuji Electric Co., Ltd. | Electrophotographic photoreceptor, method for manufacturing same, and electrophotographic apparatus using same |
| US9671705B2 (en) | 2013-07-16 | 2017-06-06 | Fuji Electric Co., Ltd. | Electrophotographic photoconductor, production method thereof, and electrophotographic apparatus |
| US10962893B2 (en) | 2016-07-22 | 2021-03-30 | Fuji Electric Co., Ltd. | Photosensitive body for electrophotography, method for producing same and electrophotographic apparatus |
| US10429752B2 (en) | 2017-02-24 | 2019-10-01 | Fuji Electric Co., Ltd. | Electrophotographic photoconductor, manufacturing method thereof, and electrophotographic apparatus using the same |
| US11036151B2 (en) | 2018-01-19 | 2021-06-15 | Fuji Electric Co., Ltd. | Electrophotographic photoreceptor, method for manufacturing same, and electrophotographic device |
| US11143976B2 (en) | 2018-01-19 | 2021-10-12 | Fuji Electric Co., Ltd. | Photoconductor having interlayer for hole injection promotion |
| JP2021092632A (en) * | 2019-12-09 | 2021-06-17 | キヤノン株式会社 | Electrophotographic photoreceptor, process cartridge and electrophotographic device |
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| JP2732697B2 (en) | 1998-03-30 |
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