JPS63271461A - Organic photosensitive body - Google Patents
Organic photosensitive bodyInfo
- Publication number
- JPS63271461A JPS63271461A JP10778087A JP10778087A JPS63271461A JP S63271461 A JPS63271461 A JP S63271461A JP 10778087 A JP10778087 A JP 10778087A JP 10778087 A JP10778087 A JP 10778087A JP S63271461 A JPS63271461 A JP S63271461A
- Authority
- JP
- Japan
- Prior art keywords
- perylene
- photoreceptor
- hydrazone
- charge
- tetracarboxydiimide
- 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
- 239000000463 material Substances 0.000 claims abstract description 29
- 239000010410 layer Substances 0.000 claims abstract description 22
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 claims abstract description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 18
- 239000002356 single layer Substances 0.000 claims abstract description 15
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
- 150000007857 hydrazones Chemical class 0.000 claims abstract description 5
- 108091008695 photoreceptors Proteins 0.000 claims description 68
- -1 3,5-dimethylphenyl Chemical group 0.000 claims description 53
- 229920005989 resin Polymers 0.000 claims description 17
- 239000011347 resin Substances 0.000 claims description 17
- 239000011230 binding agent Substances 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 230000035945 sensitivity Effects 0.000 abstract description 17
- 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 20
- 239000000049 pigment Substances 0.000 description 13
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 12
- 239000000758 substrate Substances 0.000 description 10
- 230000007423 decrease Effects 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 8
- 239000002245 particle Substances 0.000 description 8
- 230000032258 transport Effects 0.000 description 8
- 229910052782 aluminium Inorganic materials 0.000 description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 4
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 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
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 3
- 238000000975 co-precipitation Methods 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 description 3
- 230000003595 spectral effect Effects 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 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
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 206010034972 Photosensitivity reaction Diseases 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000005299 abrasion Methods 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 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
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 230000036211 photosensitivity Effects 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 2
- 229910052721 tungsten Inorganic materials 0.000 description 2
- 239000010937 tungsten Substances 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- DGVZQSMXUHGJHU-UHFFFAOYSA-N 1,2-dinitrofluoren-9-one Chemical compound C1=CC=C2C(=O)C3=C([N+]([O-])=O)C([N+](=O)[O-])=CC=C3C2=C1 DGVZQSMXUHGJHU-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
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- FLCWJWNCSHIREG-UHFFFAOYSA-N 2-(diethylamino)benzaldehyde Chemical compound CCN(CC)C1=CC=CC=C1C=O FLCWJWNCSHIREG-UHFFFAOYSA-N 0.000 description 1
- TUSYJBWUTKJDDG-UHFFFAOYSA-N 2-(n-phenylanilino)benzaldehyde Chemical compound O=CC1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 TUSYJBWUTKJDDG-UHFFFAOYSA-N 0.000 description 1
- GEKJEMDSKURVLI-UHFFFAOYSA-N 3,4-dibromofuran-2,5-dione Chemical compound BrC1=C(Br)C(=O)OC1=O GEKJEMDSKURVLI-UHFFFAOYSA-N 0.000 description 1
- FAPXNOXKLZJBMT-UHFFFAOYSA-N 4-[5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazol-2-yl]-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1C1=NN=C(C=2C=CC(=CC=2)N(C)C)O1 FAPXNOXKLZJBMT-UHFFFAOYSA-N 0.000 description 1
- XYPMAZCBFKBIFK-UHFFFAOYSA-N 9,10-dinitroanthracene Chemical compound C1=CC=C2C([N+](=O)[O-])=C(C=CC=C3)C3=C([N+]([O-])=O)C2=C1 XYPMAZCBFKBIFK-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
- 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
- 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
- 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
- HXGDTGSAIMULJN-UHFFFAOYSA-N acetnaphthylene Natural products C1=CC(C=C2)=C3C2=CC=CC3=C1 HXGDTGSAIMULJN-UHFFFAOYSA-N 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
- HUVXQFBFIFIDDU-UHFFFAOYSA-N aluminum phthalocyanine Chemical compound [Al+3].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 HUVXQFBFIFIDDU-UHFFFAOYSA-N 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
- 238000000149 argon plasma sintering Methods 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
- 229920000402 bisphenol A polycarbonate polymer Polymers 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
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 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
- 239000013078 crystal Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000002296 dynamic light scattering Methods 0.000 description 1
- 238000005516 engineering process 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
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 150000008376 fluorenones Chemical class 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
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 230000001771 impaired effect Effects 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
- 229920000554 ionomer Polymers 0.000 description 1
- 150000002545 isoxazoles Chemical class 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- BYPNIFFYJHKCFO-UHFFFAOYSA-N n,n-dimethyl-4-(2-phenyl-1,3-dihydropyrazol-5-yl)aniline Chemical compound C1=CC(N(C)C)=CC=C1C1=CCN(C=2C=CC=CC=2)N1 BYPNIFFYJHKCFO-UHFFFAOYSA-N 0.000 description 1
- JGOAZQAXRONCCI-SDNWHVSQSA-N n-[(e)-benzylideneamino]aniline Chemical compound C=1C=CC=CC=1N\N=C\C1=CC=CC=C1 JGOAZQAXRONCCI-SDNWHVSQSA-N 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
- 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
- 229910052763 palladium Inorganic materials 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
- 229920002037 poly(vinyl butyral) polymer 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
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 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
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical class C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 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
- 230000000087 stabilizing effect Effects 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229920001909 styrene-acrylic polymer Polymers 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 230000003746 surface roughness Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- NLDYACGHTUPAQU-UHFFFAOYSA-N tetracyanoethylene Chemical group N#CC(C#N)=C(C#N)C#N NLDYACGHTUPAQU-UHFFFAOYSA-N 0.000 description 1
- 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
- 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
- G03G5/0622—Heterocyclic compounds
- G03G5/0644—Heterocyclic compounds containing two or more hetero rings
- G03G5/0646—Heterocyclic compounds containing two or more hetero rings in the same ring system
- G03G5/0657—Heterocyclic compounds containing two or more hetero rings in the same ring system containing seven relevant rings
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
- G03G5/0622—Heterocyclic compounds
- G03G5/0624—Heterocyclic compounds containing one hetero ring
- G03G5/0627—Heterocyclic compounds containing one hetero ring being five-membered
- G03G5/0629—Heterocyclic compounds containing one hetero ring being five-membered containing one hetero atom
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- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- 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、有機感光体に関し、より詳しくは、電子写真
用感光体として好適な有機感光体に関する。DETAILED DESCRIPTION OF THE INVENTION <Industrial Application Field> The present invention relates to an organic photoreceptor, and more particularly to an organic photoreceptor suitable as an electrophotographic photoreceptor.
〈従来の技術と発明が解決しようとする問題点〉近年、
電子写真用感光体として、加工性がよく製造コストの面
で有利であると共に、機能設計の自由度が大きな有機感
光体が使用されている。なかでも、光照射により電荷を
発生させる電荷発生材料と、発生した電荷を輸送する電
荷輸送材料とにより、各機能を分離して高感度化等を図
るため、機能分離型の有機感光体が知られている。例え
ば、電荷輸送材料としてのポリビニルカルバゾール系光
導電体中に多環式芳香族炭化水素を含有させた単層型の
感光体(特開昭56−143438号公報)や、導電性
基板上に、電荷発生材料としてのペリレン系顔料を含有
する電荷発生層と、電荷輸送材料としての特定のヒドラ
ゾン系化合物を含有する電荷輸送層とが積層された複層
型の感光体(特開昭55−158954号公報参照)が
知られている。<Problems to be solved by conventional technology and inventions> In recent years,
As a photoreceptor for electrophotography, an organic photoreceptor is used because it has good processability and is advantageous in terms of manufacturing cost, and also has a large degree of freedom in functional design. In particular, functionally separated organic photoreceptors are becoming more and more popular because they can achieve higher sensitivity by separating each function using a charge-generating material that generates a charge when irradiated with light and a charge-transporting material that transports the generated charge. It is being For example, a single-layer type photoreceptor (Japanese Patent Application Laid-Open No. 143438/1983) in which a polycyclic aromatic hydrocarbon is contained in a polyvinylcarbazole-based photoconductor as a charge transport material, or a conductive substrate, A multilayer photoreceptor in which a charge generation layer containing a perylene pigment as a charge generation material and a charge transport layer containing a specific hydrazone compound as a charge transport material are laminated (Japanese Patent Laid-Open No. 55-158954) (see Publication No. 1) is known.
上記の単層型の感光体は、ポリビニルカルバゾール系光
導電体中に多環式芳香族炭化水素を分散し、導電性基板
に塗布し、乾燥させるだけで感光体を得ることができる
ため、生産性がよい。また、上記単層型感光体にあって
は、正帯電させることができるだけでなく、感光体の静
電潜像を現像するトナーとして、一般に負帯電するもの
が得られ易いため、トナー材料の選択幅が広く、種々の
トナー材料を使用することができるという利点がある。The single-layer photoconductor described above can be produced simply by dispersing polycyclic aromatic hydrocarbon in a polyvinylcarbazole photoconductor, coating it on a conductive substrate, and drying it. Good sex. In addition, in the case of the above-mentioned single-layer photoconductor, not only can it be positively charged, but also a toner that can be negatively charged is generally easily obtained as a toner for developing the electrostatic latent image on the photoconductor, so the selection of toner materials is advantageous. It has the advantage of being wide and allowing the use of various toner materials.
しかしながら、ポリビニルカルバゾール系光導電体中に
多環式芳香族炭化水素が分散している上記単層型の感光
体にあっては、感度が十分でなく、感光層を構成する材
料を厳密に選択しなければならず、感光層の材料の選択
幅が狭い。また、上記単層型感光体は、コロナ帯電時の
表面電位が低く、しかも残留電位が大きいだけでなく、
表面電位が繰返し使用により低下するので、繰返し特性
が十分でなく、有機感光体として十分な特性を示さない
という問題がある。However, the above-mentioned single-layer photoreceptor, in which a polycyclic aromatic hydrocarbon is dispersed in a polyvinylcarbazole photoconductor, does not have sufficient sensitivity, and the material constituting the photosensitive layer must be carefully selected. Therefore, the selection range of materials for the photosensitive layer is narrow. In addition, the above-mentioned single-layer photoreceptor not only has a low surface potential during corona charging and a large residual potential, but also
Since the surface potential decreases with repeated use, there is a problem that the repeatability is insufficient and the organic photoreceptor does not exhibit sufficient characteristics.
一方、上記複層型の感光体は、電荷発生層と電荷輸送層
とにより、各機能を分離しているため、前記単層型の感
光体とは異なり、高感度で感光材料の選択幅が広いとい
う利点がある。しかしながら、上記電荷輸送材料が一般
に正孔輸送物質であるため、感光体を負帯電させること
ができるものの、正帯電させることが困難であるため、
前記単層型感光体とは逆にトナー材料の選択幅が狭くな
る。また、上記電荷発生層の層厚が1〜2μmと薄いた
め、電荷発生層を精度よく形成しなければならないだけ
でなく、上記電荷発生層に電荷輸送層を形成しなければ
ならないので、感光体の製造工程が増し、作業性が悪く
、歩留りが低くなりコスト高となる。さらには、コロナ
放電により負帯電させると、オゾンが発生するので、複
写機等において、オゾンを排気する排気通路を設ける必
要があり、装置が大型化するという問題がある。On the other hand, the above-mentioned multi-layer type photoreceptor has a charge generation layer and a charge transport layer that separate each function, so unlike the above-mentioned single-layer type photoreceptor, it has high sensitivity and a wide selection of photosensitive materials. It has the advantage of being spacious. However, since the charge transport material is generally a hole transport substance, it is possible to negatively charge the photoreceptor, but it is difficult to charge it positively.
In contrast to the single-layer type photoreceptor, the selection range of toner materials is narrower. In addition, since the charge generation layer has a thin layer thickness of 1 to 2 μm, it is not only necessary to form the charge generation layer with high precision, but also to form a charge transport layer on the charge generation layer. This increases the number of manufacturing steps, resulting in poor workability, low yield, and high costs. Furthermore, since ozone is generated when negatively charged by corona discharge, it is necessary to provide an exhaust passage for exhausting ozone in a copying machine or the like, resulting in the problem of an increase in the size of the apparatus.
〈発明の目的〉
本発明は上記問題点に鑑みてなされたものであり、正帯
電性に優れ、感度および表面電位が高く、しかも残留電
位が小さく、安価な単層型有機感光体を提供することを
目的とする。<Object of the Invention> The present invention has been made in view of the above problems, and provides an inexpensive single-layer organic photoreceptor that has excellent positive chargeability, high sensitivity and surface potential, and low residual potential. The purpose is to
く問題点を解決するための手段および作用〉上記目的を
達成するため、本発明の有機感光体は、電荷発生材料と
電荷輸送材料と結着樹脂とからなる単層型の感光層を有
する感光体において、上記電荷発生材料が下記一般式(
1)で表されるペリレン系化合物であり、電荷輸送材料
が下記一般式(2)で表されるヒドラゾン系化合物であ
ることを特徴とするものである。Means and Effects for Solving the Problems In order to achieve the above objects, the organic photoreceptor of the present invention is a photoreceptor having a single-layer type photoreceptor layer consisting of a charge generating material, a charge transporting material, and a binder resin. In the body, the charge generating material has the following general formula (
It is a perylene compound represented by 1), and is characterized in that the charge transport material is a hydrazone compound represented by the following general formula (2).
(式中、R’ 、R” 、R’およびR4は、それぞれ
同一または異なって、低級アルキル基または低級アルコ
キシ基を示す)
(式中、R5は水素原子または低級アルキル基を示す)
以下に、本発明の詳細な説明する。(In the formula, R', R", R' and R4 are the same or different and each represents a lower alkyl group or a lower alkoxy group.) (In the formula, R5 represents a hydrogen atom or a lower alkyl group.) The present invention will be described in detail.
本発明の有機感光体は、単層型の感光層を有しており、
上記電荷発生材料としての上記一般式(1)で表される
ペリレン系化合物と、電荷輸送材料としての上記一般式
(りで表されるヒドラゾン系化合物と、結着樹脂とで構
成されている。The organic photoreceptor of the present invention has a single-layer photosensitive layer,
It is composed of a perylene compound represented by the general formula (1) as the charge generating material, a hydrazone compound represented by the general formula (RI) as the charge transporting material, and a binder resin.
上記一般式(1)および一般式(りにおける低級アルキ
ル基としては、メチ′ル、エチル、プロピル、イソプロ
ピル、ブチル、イソブチル、tert−ブチル、ペンチ
ル、ヘキシル基等の炭素数1〜6のアルキル基が例示さ
れる。The lower alkyl group in the above general formula (1) and general formula is exemplified.
また、上記一般式(1)における低級アルコキシ基とし
ては、メトキシ、′エトキシ、プロポキシ、イソプロポ
キシ、ブトキシ、イソブトキシ、tert −ブトキシ
、ペンチルオキシ、ヘキシルオ±シ基等の炭素数1〜6
のアルコキシ基が例示される。In addition, the lower alkoxy group in the above general formula (1) has 1 to 6 carbon atoms, such as methoxy, 'ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, tert-butoxy, pentyloxy, hexyloxy group, etc.
An example is an alkoxy group.
上記一般式(1)で表されるペリレン系化合物としては
、N、N−−ジ(3,5−ジメチルフェニル)ペリレン
−3,4,9,10−テトラカルボキシジイミド、N、
N=−ジ(3−メチル−5−エチルフェニル)ペリレン
−3,4,9,10−テトラカルボキシジイミド、N、
N″−ジ(3,5−ジエチルフェニル)ペリレン−3,
4,9,10−テトラカルボキシジイミド、N、N−−
ジ(3,5−ジプロピルフェニル)ペリレン−3,4,
9,10−テトラカルボキシジイミド、N、N−−ジ(
3゜5−ジイソプロピルフェニル)ペリレン−3,4゜
9.10−テトラカルボキシジイミド、N、N”−ジ(
3,5−ジブチルフェニル)ペリレン−3゜4、 9.
10−テトラカルボキシジイミド、NlN−−ジ(3,
5−ジーtert−ブチルフェニル)ペリレン−3,4
,9,10−テトラカルボキシジイミド、N、N”−ジ
(3,5−ジエチルフェニル)ペリレン−3,4,9,
10−テトラカルボキシジイミド、N、N”−ジ(3,
5−ジェキシフェニル)ペリレン−3,4,9,10−
テトラカルボキシジイミド、N、N″−ジ(3−メチル
−5−メトキシフェニル)ペリレン−3,4,9゜IO
−テトラカルボキシジイミド、N、N”−ジ(3−メチ
ル−5−エトキシフェニル)ペリレン−3,4,9,1
0−テトラカルボキシジイミド、N、N=−ジ(3−エ
チル−5−メトキシフェニル)ペリレン−3,4,9,
10−テトラカルボキシジイミド、N、N−−ジ(3−
プロピル−5−メトキシフェニル)ペリレン−3,4,
9,10−テトラカルボキシジイミド、N、N−−ジ(
3゜5−ジメトキシフェニル)ペリレン−3,4,9゜
lO−テトラカルボキシジイミド、N、N−−ジ(3,
5−ジェトキシフェニル)ペリレン−3゜4、 9.1
0−テトラカルボキシジイミド、N。The perylene compounds represented by the above general formula (1) include N,N--di(3,5-dimethylphenyl)perylene-3,4,9,10-tetracarboxydiimide, N,
N=-di(3-methyl-5-ethylphenyl)perylene-3,4,9,10-tetracarboxydiimide, N,
N″-di(3,5-diethylphenyl)perylene-3,
4,9,10-tetracarboxydiimide, N, N--
Di(3,5-dipropylphenyl)perylene-3,4,
9,10-tetracarboxydiimide, N,N--di(
3゜5-diisopropylphenyl)perylene-3,4゜9.10-tetracarboxydiimide, N,N”-di(
3,5-dibutylphenyl)perylene-3゜4, 9.
10-Tetracarboxydiimide, NlN--di(3,
5-di-tert-butylphenyl)perylene-3,4
,9,10-tetracarboxydiimide, N,N''-di(3,5-diethylphenyl)perylene-3,4,9,
10-tetracarboxydiimide, N,N”-di(3,
5-jexyphenyl)perylene-3,4,9,10-
Tetracarboxydiimide, N,N″-di(3-methyl-5-methoxyphenyl)perylene-3,4,9°IO
-tetracarboxydiimide, N,N''-di(3-methyl-5-ethoxyphenyl)perylene-3,4,9,1
0-Tetracarboxydiimide, N, N=-di(3-ethyl-5-methoxyphenyl)perylene-3,4,9,
10-tetracarboxydiimide, N,N--di(3-
Propyl-5-methoxyphenyl)perylene-3,4,
9,10-tetracarboxydiimide, N,N--di(
3゜5-dimethoxyphenyl)perylene-3,4,9゜O-tetracarboxydiimide, N,N--di(3,
5-jethoxyphenyl)perylene-3゜4, 9.1
0-tetracarboxydiimide, N.
N゛−ジ(3,5−ジプロポキシフェニル)ペリレン−
3,4,9,10−テトラカルボキシジイミド、N、N
−−ジ(3,5−ジイソプロポキシフェニル)ペリレン
−3,4,9,10−テトラカルボキシジイミド、N、
N″−ジ(3,5−ジブトキシフェニル)ペリレン−3
,4,9,10−テトラカルボキシジイミド、N、N”
−ジ(3,5−ジペンチルオキシフェニル)ペリレン−
3,4゜9.10−テトラカルボキシジイミド、N、N
−−ジ(3,5−ジヘキシルオキシフェニル)ペリレン
−3,4,9,10−テトラカルボキシジイミド等が例
示される。上記ペリレン系化合物のうち、炭素数が1〜
3のアルキル基またはアルコキシ基を存するもの、特に
、N、N−−ジ(3,5−ジメチルフェニル)ペリレン
−3,4,9,,10−テトラカルボキシジイミドが好
ましい。なお、上記ペリレン系化合物は一種または二種
以上混合して用いられる。N-di(3,5-dipropoxyphenyl)perylene-
3,4,9,10-tetracarboxydiimide, N, N
--di(3,5-diisopropoxyphenyl)perylene-3,4,9,10-tetracarboxydiimide, N,
N″-di(3,5-dibutoxyphenyl)perylene-3
,4,9,10-tetracarboxydiimide, N,N”
-di(3,5-dipentyloxyphenyl)perylene-
3,4゜9.10-tetracarboxydiimide, N, N
--Di(3,5-dihexyloxyphenyl)perylene-3,4,9,10-tetracarboxydiimide and the like are exemplified. Among the above perylene compounds, the number of carbon atoms is 1 to
Those containing 3 alkyl or alkoxy groups, particularly N,N--di(3,5-dimethylphenyl)perylene-3,4,9,,10-tetracarboxydiimide, are preferred. The above perylene compounds may be used alone or in combination of two or more.
また、上記一般式■で表されるヒドラゾン系化合物とし
ては、3−カルバゾリルアルデヒド N。Further, as the hydrazone compound represented by the above general formula (2), 3-carbazolyl aldehyde N is used.
N−ジフェニルヒト・ラゾン、N−メチル−3−カルバ
ゾリルアルデヒド N、N−ジフェニルヒドラゾン、N
−エチル−3−カルバゾリルアルデヒド N、N−ジフ
ェニルヒドラゾン、N−プロピル−3−カルバゾリルア
ルデヒド N、N−ジフェニルヒドラゾン、N−イソプ
ロピル−3−カルバゾリルアルデヒド N、N−ジフェ
ニルヒドラゾン、N−ブチル−3−カルバゾリルアルデ
ヒドN、N−ジフェニルヒドラゾン、N−インブチル−
3−カルバゾリルアルデヒド N、N−ジフェニルヒド
ラゾン、N−tart−ブチル−3−カルバゾリルアル
デヒド N、N−ジフェニルヒドラゾン、N−ペンチル
−3−カルバゾリルアルデヒド N、N−ジフェニルヒ
ドラゾン、N−へキシル−3−カルバゾリルアルデヒド
N、N−ジフェニルヒドラゾンが例示される。上記ヒ
ドラゾン系化合物のうち、炭素数1〜3のアルキル基を
有するもの、特に、N−メチル−3−カルバゾリルアル
デヒド N、N−ジフェニルヒドラゾンが好ましい。上
記ヒドラゾン系化合物は一種または二種以上混合して用
いられる。N-diphenylhydrazone, N-methyl-3-carbazolyl aldehyde N, N-diphenylhydrazone, N
-Ethyl-3-carbazolylaldehyde N,N-diphenylhydrazone, N-propyl-3-carbazolylaldehyde N,N-diphenylhydrazone, N-isopropyl-3-carbazolylaldehyde N,N-diphenylhydrazone, N-butyl-3-carbazolyl aldehyde N, N-diphenylhydrazone, N-inbutyl-
3-Carbazolylaldehyde N,N-diphenylhydrazone, N-tart-butyl-3-carbazolylaldehyde N,N-diphenylhydrazone, N-pentyl-3-carbazolylaldehyde N,N-diphenylhydrazone, N -Hexyl-3-carbazolyl aldehyde N,N-diphenylhydrazone is exemplified. Among the above hydrazone compounds, those having an alkyl group having 1 to 3 carbon atoms, particularly N-methyl-3-carbazolyl aldehyde N,N-diphenylhydrazone, are preferred. The above hydrazone compounds may be used alone or in combination of two or more.
また、上記結着樹脂としては、種々のもの、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、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、
各種の重合体が使用できるが、感光体の感度を高め、上
記ヒドラゾン系化合物等との相溶性、感光体の耐摩耗性
および繰返し特性に優れると共に結着樹脂を溶解する溶
剤の選択幅が広いポリ(4,4”−シクロヘキシリデン
ジフェニル)カーボネートが好ましい。上記ポリ(4,
4−−シクロへキシリデンジフェニル)カーボネートを
用いると、従来、溶液安定性等の点から、ジクロロメタ
ン、モノクロロベンゼン等の塩素系溶剤しか使用できな
かったビスフェノールA型ポリカーボネートと異なり、
テトラヒドロフラン、メチルエチルケトン等のケトン系
等の溶剤も使用することができるので、安全衛生上も好
ましく、取扱いが容易である。なお、上記ポリ(4,4
−−シクロへキシリデンジフェニル)カーボネートとし
ては、種々のもの、例えば、重合度50〜5000程度
のものが使用し得る。また、上記結着樹脂は一種または
二種以上混合して用いられる。In addition, various binder resins can be used, such as styrene polymers, acrylic polymers, styrene-acrylic copolymers, polyethylene, ethylene-vinyl acetate copolymers, chlorinated polyethylene, polypropylene, and ionomers. Olefin polymers such as polyvinyl chloride, vinyl chloride-vinyl acetate copolymer, polyester, alkyd resin, polyamide, polyurethane, epoxy resin, polycarbonate, polyarylate, polysulfone, diallyl phthalate resin, silicone resin, ketone resin, polyvinyl Butyral resin, polyether resin, phenol resin, photocurable resin such as epoxy acrylate, etc.
Various polymers can be used, but there is a wide selection of solvents that can increase the sensitivity of the photoreceptor, have compatibility with the above-mentioned hydrazone compounds, have excellent abrasion resistance and repeatability of the photoreceptor, and dissolve the binder resin. Poly(4,4”-cyclohexylidene diphenyl) carbonate is preferred.
When using 4-cyclohexylidene diphenyl) carbonate, unlike bisphenol A polycarbonate, for which conventionally only chlorinated solvents such as dichloromethane and monochlorobenzene could be used due to solution stability,
Since ketone solvents such as tetrahydrofuran and methyl ethyl ketone can also be used, they are preferable from the viewpoint of safety and hygiene and are easy to handle. In addition, the above poly(4,4
--As the cyclohexylidene diphenyl) carbonate, various ones can be used, for example, those having a degree of polymerization of about 50 to 5,000. Further, the above-mentioned binder resins may be used alone or in combination of two or more.
上記ペリレン系化合物とヒドラゾン系化合物と上記結着
樹脂との使用割合は、所望する有機感光体の特性等に応
じて適宜選択することができるが、結着樹脂100重量
部に対して、ペリレン系化合物2〜20重量部、好まし
くは、5〜10重量部、ヒドラゾン系化合物40〜11
0重量部、好ましくは、60〜90重量部使用される。The proportions of the perylene compound, hydrazone compound, and binder resin can be appropriately selected depending on the desired characteristics of the organic photoreceptor. 2 to 20 parts by weight of compound, preferably 5 to 10 parts by weight, 40 to 11 parts by weight of hydrazone compound
0 parts by weight, preferably 60 to 90 parts by weight are used.
ペリレン系化合物およびヒドラゾン系化合物が上記使用
量よりも少ないと、感光体の感度が十分でないばかりか
、残留電位が大きくなる。また上記範囲を越えると感光
体の耐摩耗性等が十分でなくなる。If the amount of perylene compound and hydrazone compound used is less than the above-mentioned amount, not only the sensitivity of the photoreceptor will not be sufficient, but also the residual potential will become large. Further, if the amount exceeds the above range, the abrasion resistance of the photoreceptor will not be sufficient.
なお、通常、上記ペリレン系化合物を多量に使用すると
正帯電性が十分でなくなり、少量であると感度等が低下
するが、本発明の有機感光体においては、特定のペリレ
ン系化合物とヒドラゾン系化合物とを組合せているので
、ペリレン系化合物の量が少量であっても感度および表
面電位が高く、しかも残留電位の小さな正帯電性に優れ
た有機感光体を得ることができる。Note that normally, if a large amount of the above perylene compound is used, the positive chargeability will not be sufficient, and if a small amount is used, the sensitivity etc. will decrease. As a result, even if the amount of the perylene compound is small, it is possible to obtain an organic photoreceptor with high sensitivity and surface potential, and excellent positive chargeability with a small residual potential.
また、上記ペリレン系化合物は短波長側に分光感度を有
する場合がある。従って、青色領域の色再現性が必要と
される用途においては、種々の分光増感剤を使用するの
が好ましく、特に、フタロシアニン系化合物を使用する
のが好ましい。Further, the above-mentioned perylene compounds may have spectral sensitivity on the short wavelength side. Therefore, in applications requiring color reproducibility in the blue region, it is preferable to use various spectral sensitizers, and it is particularly preferable to use phthalocyanine compounds.
上記フタロシアニン系化合物としては、種々のものが使
用しえるが、メタルフリーフタロシアニンが好ましい。Various types of phthalocyanine compounds can be used, but metal-free phthalocyanine is preferred.
上記メタルフリーフタロシアニンは、適宜の粒径を有し
ていてもよいが、平均粒径0.1μ烏以下のものが好ま
しい。メタルフリーフタロシアニンの平均粒径が0.1
μ虐を越えると感光体の感度が低下する。なお、上記平
均粒径は、光散乱法(装置名:ダイナミック光散乱光度
計)により求めたものである。The metal-free phthalocyanine may have an appropriate particle size, but preferably has an average particle size of 0.1 μm or less. The average particle size of metal-free phthalocyanine is 0.1
When the μ tolerance is exceeded, the sensitivity of the photoreceptor decreases. The above average particle diameter was determined by a light scattering method (device name: dynamic light scattering photometer).
また、メタルフリーフタロシアニンは適宜量使用するこ
とができるが、上記結着樹脂100重量部に対して0.
2〜1重量部添加するのが好ましい。添加量が0.2f
fi量部未満であると青色再現性が十分でなく、1′f
fi量部を越えるとメタルフリーフタロシアニンが赤色
領域に分光感度を有するため、赤色再現性が十分でなく
なる。Further, metal-free phthalocyanine can be used in an appropriate amount, but 0.000 parts by weight per 100 parts by weight of the above-mentioned binder resin.
It is preferable to add 2 to 1 part by weight. Addition amount is 0.2f
If it is less than fi parts, the blue reproducibility will be insufficient, and 1'f
If the fi amount is exceeded, metal-free phthalocyanine has spectral sensitivity in the red region, resulting in insufficient red reproducibility.
なお、上記メタルフリーフタロシアニンのうち、β型メ
タルフリーフタロシアニン、特に、平均粒径0.005
〜0.05μmを有するものが好ましい。上記β型メタ
ルフリーフタロシアニンの平均粒径が0.005μm未
満であると分散性が十分でなく、0,05μmを越える
と感光体の感度が低下する。In addition, among the above metal-free phthalocyanines, β-type metal-free phthalocyanine, especially the average particle size of 0.005
Those having a diameter of 0.05 μm are preferred. When the average particle size of the β-type metal-free phthalocyanine is less than 0.005 μm, the dispersibility is insufficient, and when it exceeds 0.05 μm, the sensitivity of the photoreceptor decreases.
また、上記メタルフリーフタロシアニンを含有する感光
体の安定性を高めるため、上記メタルフリーフタロシア
ニンと共に、アルミニウムフタロシアニン、チタニル7
タロシアニン等のフタロシアニン系顔料、特に銅フタロ
シアニンを併用するのが好ましい。また、銅フタロシア
ニンは、適宜量使用することができるが、上記メタルフ
リーフタロシアニンに対して1〜10重量%、特に3〜
10重量%使用するのが好ましい。銅フタロシアニンの
量が1重量%未満であると前記メタルフリーフタロシア
ニンを安定化するのに十分でなく、10重量%を越える
と表面電位が低下する。なお、上記銅フタロシアニンの
量が多くなるにつれてメタルフリーフタロシアニンの安
定化効果が高まると共に、感光体の残留電位も低下する
。In addition, in order to increase the stability of the photoreceptor containing the metal-free phthalocyanine, aluminum phthalocyanine, titanyl 7
It is preferable to use a phthalocyanine pigment such as talocyanine, especially copper phthalocyanine. Further, copper phthalocyanine can be used in an appropriate amount, but 1 to 10% by weight, particularly 3 to 10% by weight, based on the metal-free phthalocyanine.
Preferably, 10% by weight is used. If the amount of copper phthalocyanine is less than 1% by weight, it is not sufficient to stabilize the metal-free phthalocyanine, and if it exceeds 10% by weight, the surface potential will decrease. Note that as the amount of copper phthalocyanine increases, the stabilizing effect of metal-free phthalocyanine increases, and the residual potential of the photoreceptor also decreases.
また、上記銅フタロシアニンは、前記β型メタルフリー
フタロシアニンと組合せて使用するのがより一層好まし
く、この場合、銅フタロシアニンとして平均粒径0.0
01μm以下のものを使用するのが好ましい。特に、銅
フタロシアニンの量を少なくして安定かつ残留電位の小
さな有機感光体を得るため、上記銅フタロシアニンをメ
タルフリーフタロシアニンと共に共沈させたものが好ま
しい。上記の共沈は、常法により行なうことができ、例
えば、銅フタロシアニンの製造時において銅フタロシア
ニンとメタルフリーフタロシアニンとの硫酸溶液を水中
等に滴下することにより行なうことができる。上記の共
沈により得られたフタロシアニンは、銅フタロシアニン
が微粒子となると共に、感光体の熱履歴による電気特性
の劣化が殆どなくなるだけでなく、残留電位が小さく色
再現性等に優れる感光体が得られる。なお、上記共沈法
によるフタロシアニンにおいては、少量にて青色再現性
を高めるため、銅フタロシアニンとしては平均粒径0,
001μm以下のものが好ましい。Further, it is even more preferable to use the copper phthalocyanine in combination with the β-type metal-free phthalocyanine, and in this case, the average particle size of the copper phthalocyanine is 0.0.
It is preferable to use one with a diameter of 0.01 μm or less. In particular, in order to obtain a stable organic photoreceptor with a small residual potential by reducing the amount of copper phthalocyanine, it is preferable to co-precipitate the copper phthalocyanine with metal-free phthalocyanine. The coprecipitation described above can be carried out by a conventional method, for example, by dropping a sulfuric acid solution of copper phthalocyanine and metal-free phthalocyanine into water or the like during production of copper phthalocyanine. The phthalocyanine obtained by the above-mentioned coprecipitation not only becomes fine particles of copper phthalocyanine, but also almost eliminates deterioration of electrical properties due to the thermal history of the photoreceptor, and also provides a photoreceptor with low residual potential and excellent color reproducibility. It will be done. In addition, in the phthalocyanine produced by the above coprecipitation method, in order to improve blue reproducibility with a small amount, the average particle size of the copper phthalocyanine is 0,
001 μm or less is preferable.
なお、上記の組成よりなる有機感光体は、感光特性等を
阻害しない範囲で、他の電荷発生材料、電荷輸送材料等
を使用してもよい。上記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、ピ
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、
トリフェニルメタン系顔料、スレン系顔料、トルイジン
系顔料、ピラゾリン系顔料、他のペリレン系顔料、キナ
クリドン系顔料等が例示される。また、上記電荷輸送材
料としては、例えば、テトラシアノエチレン、2,4.
7−)ジニトロ−9−フルオレノン等のフルオレノン系
化合物、2,4.8−トリニドロチオキサントン、ジニ
トロアントラセン等のニトロ化化合物、無水コハク酸、
無水マレイン酸、ジブロモ無水マレイン酸、2,5−ジ
(4−ジメチルアミノフェニル)−1,3,4−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)ピラゾリン等のピラゾリン系化合物、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、縮合多環族化合
物等が例示される。また、ターフェニル、ハロナフトキ
ノン類、アセナフチレン等、従来公知の増感剤を用いて
もよい。Note that the organic photoreceptor having the above composition may contain other charge generating materials, charge transporting materials, etc., as long as the photosensitive properties etc. are not impaired. Examples of the charge generating material include selenium, selenium-tellurium, amorphous silicon, pyrylium salt, azo pigment, disazo pigment, anthanthrone pigment, phthalocyanine pigment, indigo pigment,
Examples include triphenylmethane pigments, threne pigments, toluidine pigments, pyrazoline pigments, other perylene pigments, and quinacridone pigments. Further, examples of the charge transporting material include tetracyanoethylene, 2,4.
7-) Fluorenone compounds such as dinitro-9-fluorenone, nitrated compounds such as 2,4.8-trinidrothioxanthone and dinitroanthracene, succinic anhydride,
Maleic anhydride, dibromomaleic anhydride, oxadiazole compounds such as 2,5-di(4-dimethylaminophenyl)-1,3,4-oxadiazole, 9-(4-
styryl compounds such as diethylaminostyryl)anthracene, carbazole compounds such as polyvinylcarbazole, pyrazoline compounds such as 1-phenyl-3-(p-dimethylaminophenyl)pyrazoline, indole compounds, oxazole compounds, isoxazole compounds , thiazole compounds, thiadiazole compounds,
Examples include nitrogen-containing cyclic compounds such as imidazole compounds, pyrazole compounds, and triazole compounds, and fused polycyclic compounds. Furthermore, conventionally known sensitizers such as terphenyl, halonaphthoquinones, and acenaphthylene may be used.
上記のペリレン系化合物、ヒドラゾン系化合物および結
着樹脂等を含有する有機感光体の感光層は、適宜の厚み
°を有していてもよいが、3〜50μm、特に、5〜2
0μ鳳の厚みを有するものが好ましく、上記ペリレン系
化合物等の分散液を調整し、導電性基板に塗布すると共
に、溶媒を除去することにより形成される。The photosensitive layer of the organic photoreceptor containing the above-mentioned perylene compound, hydrazone compound, binder resin, etc. may have an appropriate thickness, preferably 3 to 50 μm, particularly 5 to 2 μm.
It is preferable to have a thickness of 0 μm, and is formed by preparing a dispersion of the above-mentioned perylene compound, applying it to a conductive substrate, and removing the solvent.
上記導電性基板は、シート状やドラム状のいずれであっ
てもよく、基板自体が導電性を有するか、基板の表面が
導電性を有し、使用に際し十分な機械的強度を有するも
のが好ましい。上記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、パラジウム、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。上記導電性基板のうち、アルミニウ
ムが好ましく、特に、アルミニウムの結晶粒が表面に存
在せず、複写画像等において黒点やピンホール等が発生
するのを防止すると共に、上記ペリレン系化合物、ヒド
ラゾン系化合物等を含有する感光層と基板との密着性を
よくするため、アルマイト処理されたアルミニウム、中
でもアルマイト処理層の膜厚が5〜12μ履であり、表
面粗さが1.5S以下のアルマイト処理されたアルミニ
ウムが好ましい。The above-mentioned conductive substrate may be in the form of a sheet or a drum, and it is preferable that the substrate itself is conductive or the surface of the substrate is conductive and has sufficient mechanical strength when used. . Various conductive materials can be used as the conductive substrate, such as aluminum, copper,
tin, platinum, gold, silver, vanadium, molybdenum, chromium,
Examples include simple metals such as cadmium, titanium, nickel, palladium, indium, stainless steel, and brass, plastic materials on which the above metals are vapor-deposited or laminated, and glass coated with aluminum iodide, tin oxide, indium oxide, etc. . Among the above-mentioned conductive substrates, aluminum is preferable, and in particular, aluminum crystal grains are not present on the surface, preventing black spots and pinholes from occurring in copied images, etc., and the above-mentioned perylene-based compounds and hydrazone-based compounds are preferred. In order to improve the adhesion between the photosensitive layer and the substrate, the alumite-treated aluminum, especially the alumite-treated aluminum with a film thickness of 5 to 12 μm and a surface roughness of 1.5S or less, is used. Aluminum is preferred.
また、上記分散液の調製に際しては、使用される結着樹
脂等の種類に応じて種々の有機溶剤を使用することがで
きる。上記溶剤としては、n−へキサン、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、エチレングリコールジエチルエーテル、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。な
お、上記分散液を調製する際、分散性、塗工性等をよく
するため、界面活性剤、レベリング剤等を併用してもよ
い。Further, when preparing the above-mentioned dispersion liquid, various organic solvents can be used depending on the type of binder resin and the like used. The above-mentioned solvents include 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. , diethyl ether,
Examples of various solvents include ethers such as tetrahydrofuran, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, and diethylene glycol dimethyl ether, ketones such as acetone, methyl ethyl ketone, and cyclohexanone, esters such as ethyl acetate and methyl acetate, dimethyl formamide, and dimethyl sulfoxide. They can be used singly or in combination of two or more. In addition, when preparing the above-mentioned dispersion, a surfactant, a leveling agent, etc. may be used in combination in order to improve dispersibility, coating properties, etc.
また、上記分散液は、従来慣用の方法、例えば、ボール
ミル、ペイントシェーカー、サンドミル、アトライター
、超音波分散器等を用いて調製することができ、得られ
た分散液を前記導電性基板に塗布し、加熱して溶剤を除
去することにより、本発明の有機感光体を得ることがで
きる。Further, the above-mentioned dispersion liquid can be prepared using a conventional method such as a ball mill, a paint shaker, a sand mill, an attritor, an ultrasonic disperser, etc., and the obtained dispersion liquid is applied to the conductive substrate. The organic photoreceptor of the present invention can be obtained by heating and removing the solvent.
本発明の有機感光体の感光層は、特定のペリレン系化合
物およびヒドラゾン系化合物を含有しているため、正帯
電性に優れると共に、単層型の構造を有する感光体であ
りながら、感度および表面電位が高く、しかも残留電位
が小さい。また、単層型の感光体であるため、安価な有
機感光体を歩留りよく容易に製造することができる。従
って、本発明の有機感光体は、複写機、レーザプリンタ
ー等、種々の用途に使用される感光体として有用である
。The photosensitive layer of the organic photoreceptor of the present invention contains a specific perylene compound and a hydrazone compound, so it has excellent positive chargeability, and although it is a photoreceptor with a single-layer structure, it has a high sensitivity and surface High potential and low residual potential. Further, since it is a single-layer type photoreceptor, an inexpensive organic photoreceptor can be easily manufactured with high yield. Therefore, the organic photoreceptor of the present invention is useful as a photoreceptor used in various applications such as copying machines and laser printers.
〈実施例〉
以下に、実施例に基づき、この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
N、N−−ジ(3,5−ジメチルフェニル)ペリレン−
3,4,9,10−テトラカルボキシジイミド8重量部
、N−メチル−3−カルバゾリルアルデヒド N、N−
ジフェニルヒドラゾン75重量部、ポリエステル(東洋
紡績(株)社製商品名バイロンRV200)100重量
部および所定量のテトラヒドロフランを用い、超音波分
散器にて分散液を調製すると共に、アルマイト処理され
たアルミニウム板上に塗布し、厚み約20μ膳の感光層
を有する有機感光体を作製した。Example 1 N,N--di(3,5-dimethylphenyl)perylene-
8 parts by weight of 3,4,9,10-tetracarboxydiimide, N-methyl-3-carbazolyl aldehyde N,N-
A dispersion liquid was prepared using an ultrasonic disperser using 75 parts by weight of diphenylhydrazone, 100 parts by weight of polyester (product name: Vylon RV200 manufactured by Toyobo Co., Ltd.) and a predetermined amount of tetrahydrofuran, and an alumite-treated aluminum plate was prepared. An organic photoreceptor having a photosensitive layer having a thickness of about 20 μm was prepared by coating the photoreceptor on top of the photoreceptor.
実施例2 実施例1のN−メチル−3−カルバゾリルアル。Example 2 N-Methyl-3-carbazolyl of Example 1.
デヒド N、N−ジフェニルヒドラゾンに代えて、N−
イソプロピル−3−カルバゾリルアルデヒドN、N−ジ
フェニルヒドラゾンを用いて、上記実施例1と同様にし
て有機感光体を作製した。Instead of dehyde N,N-diphenylhydrazone, N-
An organic photoreceptor was prepared in the same manner as in Example 1 using isopropyl-3-carbazolyl aldehyde N,N-diphenylhydrazone.
実施例3
実施例1のN、N−−ジ(3,5−ジメチルフェニル)
ペリレン−3,4,9,10−テトラカルボキシジイミ
ドに代えて、N、N−−ジ(3,5−ジメトキシフェニ
ル)ペリレン−3,4,9゜lO−テトラカルボキシジ
イミドを用いて、上記実施例1と同様にして有機感光体
を作製した。Example 3 N,N--di(3,5-dimethylphenyl) of Example 1
In place of perylene-3,4,9,10-tetracarboxydiimide, N,N--di(3,5-dimethoxyphenyl)perylene-3,4,9°lO-tetracarboxydiimide is used to carry out the above procedure. An organic photoreceptor was produced in the same manner as in Example 1.
実施例4
実施例1のペリレン系化合物およびヒドラゾン系化合物
に代えて、N、N−−ジ(3,5−ジメトキシフェニル
)ペリレン−3,4,9,10−テトラカルボキシジイ
ミドおよびN−エチル−3−カルバゾリルアルデヒド
N、N−ジフェニルヒドラゾンを用い、上記実施例1と
同様にして有機感光体を作製した。Example 4 In place of the perylene compound and hydrazone compound of Example 1, N,N--di(3,5-dimethoxyphenyl)perylene-3,4,9,10-tetracarboxydiimide and N-ethyl- 3-carbazolyl aldehyde
An organic photoreceptor was prepared in the same manner as in Example 1 using N,N-diphenylhydrazone.
比較例1
実施例1のN−メチル−3−カルバゾリルアルデヒド
N、N−ジフェニルヒドラゾンに代えて、N、N−ジエ
チルアミノベンズアルデヒド N。Comparative Example 1 N-methyl-3-carbazolyl aldehyde of Example 1
N,N-diethylaminobenzaldehyde N instead of N,N-diphenylhydrazone.
N−ジフェニルヒドラゾンを用いて、上記実施例1と同
様にして有機感光体を作製した。An organic photoreceptor was prepared in the same manner as in Example 1 using N-diphenylhydrazone.
比較例2
実施例1のN−メチル−3−カルバゾリルアルデヒド
N、N−ジフェニルヒドラゾンに代えて、N、N−ジフ
ェニルアミノベンズアルデヒド N。Comparative Example 2 N-methyl-3-carbazolyl aldehyde of Example 1
N,N-diphenylaminobenzaldehyde N instead of N,N-diphenylhydrazone.
N−ジフェニルヒドラゾンを用い、上記実施例1と同様
にして有機感光体を作製した。An organic photoreceptor was prepared in the same manner as in Example 1 using N-diphenylhydrazone.
比較例3
実施例1のペリレン系化合物およびヒドラゾン系化合物
に代えて、N、N″−ジメチルペリレン−3,4,9,
10−テトラカルボキシジイミドおよびN−エチル−6
−メドキシー3−カルバゾリルアルデヒド N−メチル
−N−フェニルヒドラゾンを用い、上記実施例1と同様
にして有機感光体を作製した。Comparative Example 3 In place of the perylene compound and hydrazone compound of Example 1, N,N″-dimethylperylene-3,4,9,
10-tetracarboxydiimide and N-ethyl-6
-Medoxy 3-carbazolylaldehyde An organic photoreceptor was prepared in the same manner as in Example 1 using N-methyl-N-phenylhydrazone.
そして、上記の電子写真用感光体の帯電特性、感光特性
を調べるため、静電複写紙試験装置(川口電機社製、5
P−428型)を用いて、+6.OKVの条件でコロナ
放電を行なうことにより、前記各実施例および比較例の
有機感光体を正に帯電させた。In order to investigate the charging characteristics and photosensitivity characteristics of the above-mentioned electrophotographic photoreceptor, an electrostatic copying paper tester (manufactured by Kawaguchi Electric Co., Ltd., 5
P-428 type), +6. The organic photoreceptors of each of the Examples and Comparative Examples were positively charged by performing corona discharge under OKV conditions.
なお、各感光体の表面電位V a、p、 (V)を測定
すると共に、タングステンランプを用いて、感光体表面
の照度がIOルックスとなるように調整してタングステ
ンランプにより露光し、上記表面電位V s、p、が1
/2となるまでの時間を求め、半減露光量El/2(μ
J/−)を算出した。また、露光後、0.15秒経過後
の表面電位を残留電位V r、p。In addition, the surface potential V a, p, (V) of each photoreceptor was measured, and the surface of the photoreceptor was exposed to light using a tungsten lamp with the illuminance adjusted to IO lux using a tungsten lamp. The potential V s,p is 1
/2, and find the half-decreased exposure amount El/2 (μ
J/-) was calculated. In addition, the surface potential after 0.15 seconds has passed after exposure is the residual potential V r,p.
(V)とした。また、1000回の繰返し使用により表
面電位が低下するか否か併せて調べた。なお、上記感光
体の繰返し使用により、感光体の表面電位が殆ど低下し
ないものを01大きく低下し、実用性に欠けるものをX
として評価した。(V). In addition, it was also investigated whether the surface potential would decrease after repeated use 1000 times. In addition, due to repeated use of the photoreceptor, the surface potential of the photoreceptor is rated 01 for those that hardly decrease and those that are impractical due to a large decrease in surface potential.
It was evaluated as
上記実施例および比較例で得られた各有機感光体の帯電
特性、感光特性および繰返し特性の結果を表に示す。The results of the charging characteristics, photosensitivity characteristics, and repeatability characteristics of each organic photoreceptor obtained in the above Examples and Comparative Examples are shown in the table.
(以下、余白)
表から明らかなように、本発明の有機感光体は、いずれ
も半減露光量が小さく、感度がよいと共に、残留電位が
小さいことが判明した。また、実施例のものは、いずれ
も繰返し使用しても残留電位が蓄積せず、残留電位が大
きくなることもなく繰返し特性に優れていることが判明
した。これに対して、比較例の感光体は、いずれも感度
が十分でなく、残留電位が高いものであった。特に、比
較例1のものは繰返し使用により表面電位が大きく低下
し、繰返し特性が十分でなかった。また、比較例3のも
のは、表面電位が低いものであった。(Hereinafter, blank space) As is clear from the table, all of the organic photoreceptors of the present invention had a small half-life exposure, good sensitivity, and a small residual potential. Further, it was found that all of the examples did not accumulate residual potential even after repeated use, did not have a large residual potential, and had excellent repeatability. On the other hand, all of the photoreceptors of Comparative Examples had insufficient sensitivity and high residual potential. In particular, in Comparative Example 1, the surface potential significantly decreased due to repeated use, and the repeatability was not sufficient. Moreover, the surface potential of Comparative Example 3 was low.
〈発明の効果〉
以上のように、本発明の有機感光体によれば、感光層が
、特定のペリレン系化合物とヒドラゾン系化合物と結着
樹脂とからなるため、正帯電性に優れると共に、単層型
の構造を有する感光体でありながら、感度および表面電
位が高く、しかも残留電位が小さい。また、単層型の感
光体であるため、歩留りよく容易に製造することができ
安価であるという特有の効果を奏する。<Effects of the Invention> As described above, according to the organic photoreceptor of the present invention, since the photosensitive layer is composed of a specific perylene compound, a hydrazone compound, and a binder resin, it has excellent positive chargeability and Although it is a photoreceptor with a layered structure, it has high sensitivity and surface potential, and low residual potential. Furthermore, since it is a single-layer type photoreceptor, it has the unique advantage of being easily manufactured with a high yield and being inexpensive.
Claims (1)
単層型の感光層を有する感光体において、上記電荷発生
材料が下記一般式(1)で表されるペリレン系化合物で
あり、電荷輸送材料が下記一般式(2)で表されるヒド
ラゾン系化合物であることを特徴とする有機感光体。 ▲数式、化学式、表等があります▼(1) (式中、R^1、R^2、R^3およびR^4は、それ
ぞれ同一または異なって、低級アルキル基または低級ア
ルコキシ基を示す) ▲数式、化学式、表等があります▼(2) (式中、R^5は水素原子または低級アルキル基を示す
) 2、ペリレン系化合物が、N,N′−ジ(3,5−ジメ
チルフェニル)ペリレン−3,4,9,10−テトラカ
ルボキシジイミドである上記特許請求の範囲第1項記載
の有機感光体。 3、ヒドラゾン系化合物が、N−メチル−3−カルバゾ
リルアルデヒドN,N−ジフェニルヒドラゾンである上
記特許請求の範囲第1項記載の有機感光体。 4、感光層が、結着樹脂100重量部に対して、ペリレ
ン系化合物2〜20重量部およびヒドラゾン系化合物4
0〜110重量部含有する上記特許請求の範囲第1項記
載の有機感光体。[Scope of Claims] 1. A photoreceptor having a single-layer photosensitive layer comprising a charge-generating material, a charge-transporting material, and a binder resin, wherein the charge-generating material is perylene represented by the following general formula (1). An organic photoreceptor, which is a hydrazone-based compound and whose charge transport material is a hydrazone-based compound represented by the following general formula (2). ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (1) (In the formula, R^1, R^2, R^3, and R^4 are the same or different and represent a lower alkyl group or a lower alkoxy group.) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(2) (In the formula, R^5 represents a hydrogen atom or a lower alkyl group) 2. Perylene compounds are N,N'-di(3,5-dimethylphenyl) ) The organic photoreceptor according to claim 1, which is perylene-3,4,9,10-tetracarboxydiimide. 3. The organic photoreceptor according to claim 1, wherein the hydrazone compound is N-methyl-3-carbazolylaldehyde N,N-diphenylhydrazone. 4. The photosensitive layer contains 2 to 20 parts by weight of a perylene compound and a hydrazone compound based on 100 parts by weight of the binder resin.
The organic photoreceptor according to claim 1, containing 0 to 110 parts by weight.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP10778087A JPH0797223B2 (en) | 1987-04-30 | 1987-04-30 | Organic photoconductor |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP10778087A JPH0797223B2 (en) | 1987-04-30 | 1987-04-30 | Organic photoconductor |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS63271461A true JPS63271461A (en) | 1988-11-09 |
JPH0797223B2 JPH0797223B2 (en) | 1995-10-18 |
Family
ID=14467833
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP10778087A Expired - Lifetime JPH0797223B2 (en) | 1987-04-30 | 1987-04-30 | Organic photoconductor |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH0797223B2 (en) |
-
1987
- 1987-04-30 JP JP10778087A patent/JPH0797223B2/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
JPH0797223B2 (en) | 1995-10-18 |
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