JPH0118417B2 - - Google Patents
Info
- Publication number
- JPH0118417B2 JPH0118417B2 JP57214037A JP21403782A JPH0118417B2 JP H0118417 B2 JPH0118417 B2 JP H0118417B2 JP 57214037 A JP57214037 A JP 57214037A JP 21403782 A JP21403782 A JP 21403782A JP H0118417 B2 JPH0118417 B2 JP H0118417B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- substituted
- unsubstituted
- formula
- general formula
- 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.)
- Expired
Links
- 108091008695 photoreceptors Proteins 0.000 claims description 31
- -1 bisazo compound Chemical class 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 2
- 125000002837 carbocyclic group Chemical group 0.000 claims description 2
- 125000006575 electron-withdrawing group Chemical group 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 2
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims 1
- 239000010410 layer Substances 0.000 description 37
- 229920005989 resin Polymers 0.000 description 18
- 239000011347 resin Substances 0.000 description 18
- 230000032258 transport Effects 0.000 description 14
- 239000000126 substance Substances 0.000 description 13
- 150000001716 carbazoles Chemical class 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 230000035945 sensitivity Effects 0.000 description 6
- 239000011230 binding agent Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 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
- 102100039497 Choline transporter-like protein 3 Human genes 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 101000889279 Homo sapiens Choline transporter-like protein 3 Proteins 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 229920006026 co-polymeric resin Polymers 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229920005668 polycarbonate resin Polymers 0.000 description 3
- 239000004431 polycarbonate resin Substances 0.000 description 3
- 229910052711 selenium Inorganic materials 0.000 description 3
- 239000011669 selenium Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- WUPHOULIZUERAE-UHFFFAOYSA-N 3-(oxolan-2-yl)propanoic acid Chemical compound OC(=O)CCC1CCCO1 WUPHOULIZUERAE-UHFFFAOYSA-N 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- 239000004640 Melamine resin Substances 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000004419 Panlite Substances 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- 229920002433 Vinyl chloride-vinyl acetate copolymer Polymers 0.000 description 2
- 229920000180 alkyd Polymers 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910052980 cadmium sulfide Inorganic materials 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 238000010030 laminating Methods 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 150000004866 oxadiazoles Chemical class 0.000 description 2
- 229920001568 phenolic resin Polymers 0.000 description 2
- 239000005011 phenolic resin Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 229920001225 polyester resin Polymers 0.000 description 2
- 239000004645 polyester resin Substances 0.000 description 2
- 229920005749 polyurethane resin Polymers 0.000 description 2
- 150000003219 pyrazolines Chemical class 0.000 description 2
- 229960005265 selenium sulfide Drugs 0.000 description 2
- 229920002050 silicone resin Polymers 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
- VHQGURIJMFPBKS-UHFFFAOYSA-N 2,4,7-trinitrofluoren-9-one Chemical compound [O-][N+](=O)C1=CC([N+]([O-])=O)=C2C3=CC=C([N+](=O)[O-])C=C3C(=O)C2=C1 VHQGURIJMFPBKS-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- 229910001369 Brass Inorganic materials 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 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
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- YSVZGWAJIHWNQK-UHFFFAOYSA-N [3-(hydroxymethyl)-2-bicyclo[2.2.1]heptanyl]methanol Chemical compound C1CC2C(CO)C(CO)C1C2 YSVZGWAJIHWNQK-UHFFFAOYSA-N 0.000 description 1
- 238000012644 addition polymerization Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 239000010951 brass Substances 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- QJNYIFMVIUOUSU-UHFFFAOYSA-N chloroethene;ethenyl acetate;furan-2,5-dione Chemical compound ClC=C.CC(=O)OC=C.O=C1OC(=O)C=C1 QJNYIFMVIUOUSU-UHFFFAOYSA-N 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- KRWWZDVIEFSIOT-UHFFFAOYSA-N ethenyl acetate;furan-2,5-dione Chemical compound CC(=O)OC=C.O=C1OC(=O)C=C1 KRWWZDVIEFSIOT-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- CPBQJMYROZQQJC-UHFFFAOYSA-N helium neon Chemical compound [He].[Ne] CPBQJMYROZQQJC-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-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
- 229940102253 isopropanolamine Drugs 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 239000000113 methacrylic resin Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 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
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc 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
- G03G5/0601—Acyclic or carbocyclic compounds
- G03G5/0612—Acyclic or carbocyclic compounds containing nitrogen
- G03G5/0616—Hydrazines; Hydrazones
-
- 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
- G03G5/0601—Acyclic or carbocyclic compounds
- G03G5/0612—Acyclic or carbocyclic compounds containing nitrogen
- G03G5/0614—Amines
- G03G5/06142—Amines arylamine
- G03G5/06147—Amines arylamine alkenylarylamine
- G03G5/061473—Amines arylamine alkenylarylamine plural alkenyl groups linked directly to the same aryl group
-
- 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
- G03G5/0601—Acyclic or carbocyclic compounds
- G03G5/0612—Acyclic or carbocyclic compounds containing nitrogen
- G03G5/0614—Amines
- G03G5/06142—Amines arylamine
- G03G5/06147—Amines arylamine alkenylarylamine
-
- 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
-
- 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
- G03G5/0635—Heterocyclic compounds containing one hetero ring being six-membered
- G03G5/0637—Heterocyclic compounds containing one hetero ring being six-membered containing one hetero atom
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- 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
- G03G5/0664—Dyes
- G03G5/0666—Dyes containing a methine or polymethine group
- G03G5/0668—Dyes containing a methine or polymethine group containing only one methine or polymethine group
-
- 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
- G03G5/0664—Dyes
- G03G5/0666—Dyes containing a methine or polymethine group
- G03G5/0668—Dyes containing a methine or polymethine group containing only one methine or polymethine group
- G03G5/067—Dyes containing a methine or polymethine group containing only one methine or polymethine group containing hetero 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
- G03G5/0664—Dyes
- G03G5/0675—Azo dyes
- G03G5/0679—Disazo dyes
- G03G5/0683—Disazo dyes containing polymethine or anthraquinone groups
-
- 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
- G03G5/0664—Dyes
- G03G5/0675—Azo dyes
- G03G5/0679—Disazo dyes
- G03G5/0683—Disazo dyes containing polymethine or anthraquinone groups
- G03G5/0685—Disazo dyes containing polymethine or anthraquinone groups containing hetero rings in the part of the molecule between the azo-groups
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Photoreceptors In Electrophotography (AREA)
Description
本発明は、導電性支持体上に、キヤリア発生相
とキヤリア輸送相とを組合せて成る感光層を設け
た電子写真感光体に関するものである。
現在までに、可視光を吸収して荷電キヤリア
(以下単に「キヤリア」という。)を発生するキヤ
リア発生物質(以下「CGM」という。)を含有し
て成るキヤリア発生層(以下「CGL」という。)
と、このCGLにおいて発生した正又は負のキヤ
リアの何れか一方又は両方を輸送するキヤリア輸
送物質(以下「CTM」という。)を含有して成る
キヤリア輸送層(以下「CTL」という。)とを組
合せることにより、電子写真感光体の感光層を構
成せしめることが提案されている。このように、
キヤリアの発生と、その輸送という感光層におい
て必要な2つの基礎的機能を、別個の層に分担せ
しめることにより、感光層の構成に用い得る物質
の選択範囲が広範となる上、各機能を最適に果す
物質又は物質系を独立に選定することが可能とな
り、又そうすることにより、電子写真プロセスに
おいて要求される諸特性、例えば帯電せしめたと
きの表面電位が高く、電荷保持能が大きく、光感
度が高く、又反復使用における安定性が大きい等
の優れた特性を有する電子写真感光体を構成せし
めることが可能となる。
従来このような感光層としては、例えば次のよ
うなものが知られている。
(1) 無定形セレン又は硫化カドミウムより成る
CGLと、ポリ―N―ビニルカルバゾールより
成るCTLとを積層せしめた構成。
(2) 無定形セレン又は硫化カドミウムより成る
CGLと、2,4,7―トリニトロ―9―フル
オレノンを含有するCTLとを積層せしめた構
成。
(3) ベリレン誘導体より成るCGLと、オキサジ
アゾール誘導体を含有するCTLとを積層せし
めた構成(米国特許第3871882号明細書参照)。
(4) クロルダイヤンブルー又はメチルスカリリウ
ムより成るCGLと、ピラゾリン誘導体を含有
するCTLとを積層せしめた構成(特開昭51―
90827号公報参照)。
(5) 無定形セレン又はその合金より成るCGLと、
ポリアリールアルカン系芳香族アミノ化合物を
含有するCTLとを積層せしめた構成(特願昭
52―147251号明細書)。
(6) ペリレン誘導体を含有するCGLと、ポリア
リールアルカン系芳香族アミノ化合物を含有す
るCTLとを積層せしめた構成(特願昭53―
19907号明細書)。
このようにこの種の感光層としては多くのもの
が知られてはいるが、斯かる感光層を有する従来
の電子写真感光体においては反復して電子写真プ
ロセスに供したときの感光層の電気的疲労が激し
くて使用寿命が非常に短い欠点を有する。
例えば、繰り返して電子写真プロセスに供した
ときに、当該電子写真感光体の電位の履歴状態が
安定に維持されず、安定した画像形成特性を得る
ことができない。
また、特定のビスアゾ化合物をCGMとして用
いることが例えば特開昭55―117151号公報、特開
昭54―145142号公報等に開示されているが、この
CGMと組合せ得るとされているCTMとの組合せ
においても、なお上述の欠点が相当に大きい。こ
のことからも理解されるように、ある特定のキヤ
リア発生物質に対して有効なキヤリア輸送物質
が、他のキヤリア発生物質に対して常に有効な訳
ではなく、又特定のキヤリア輸送物質に対して有
効なキヤリア発生物質が、他のキヤリア輸送物質
に対して常に有効であるとも言うことができな
い。両物質の組合せが不適当な場合には電子写真
感度が低くなるばかりでなく、特に低電界時の放
電効率が悪いため、所謂残留電位が大きくなり、
最悪の場合には反復して使用する度に電位が蓄積
し、実用上電子写真の用途に供し得なくなる。
このようにキヤリア発生相の構成物質とキヤリ
ア輸送相の構成物質との好適な組合せについては
法則的な選択手段はなく、多くの物質群の中から
有利な組合せを実践的に決定する必要がある。
本発明は、キヤリア発生相とキヤリア輸送相と
を組合せて成る感光層を具え、大きな感度を有
し、しかも繰り返して電子写真プロセスに供した
ときにも電位の履歴状態が安定に維持され、常に
良好な可視画像を形成することのできる電子写真
感光体を提供することを目的とする。
以上の目的は、キヤリア発生相とキヤリア輸送
相とを組合せて成る感光層を導電性支持体上に設
けて成る電子写真感光体において、前記キヤリア
発生相が下記一般式〔〕または一般式〔′〕
で示されるビスアゾ化合物を含有し、前記キヤリ
ア輸送相が下記一般式〔〕で示されるカルバゾ
ール誘導体を含有することを特徴とする電子写真
感光体によつて達成される。
一般式〔〕
一般式〔′〕
〔式中、
Ar1,Ar2およびAr3:それぞれ置換、未置換の炭
素環式芳香族環基、
R1またはR2:それぞれシアノ基、ニトロ基、ハ
ロゲン原子より選ばれた電子吸引性基、
A:
The present invention relates to an electrophotographic photoreceptor in which a photosensitive layer comprising a combination of a carrier generation phase and a carrier transport phase is provided on a conductive support. To date, carrier generation layers (hereinafter referred to as ``CGL'') containing a carrier generation substance (hereinafter referred to as ``CGM'') that absorbs visible light and generates charged carriers (hereinafter simply referred to as ``carriers''). )
and a carrier transport layer (hereinafter referred to as "CTL") containing a carrier transport material (hereinafter referred to as "CTM") that transports either or both of the positive and negative carriers generated in this CGL. It has been proposed that a photosensitive layer of an electrophotographic photoreceptor can be constructed by combining these materials. in this way,
By assigning the two basic functions necessary for the photosensitive layer, carrier generation and transport, to separate layers, the range of materials that can be used in the composition of the photosensitive layer is widened, and each function can be optimized. By doing so, it becomes possible to independently select materials or material systems that achieve the desired properties in the electrophotographic process, such as a high surface potential when charged, a large charge retention ability, and a high resistance to light. It becomes possible to construct an electrophotographic photoreceptor having excellent characteristics such as high sensitivity and great stability in repeated use. Conventionally, as such a photosensitive layer, the following ones are known, for example. (1) Consisting of amorphous selenium or cadmium sulfide
A structure in which CGL and CTL made of poly-N-vinylcarbazole are laminated. (2) Consisting of amorphous selenium or cadmium sulfide
A structure in which CGL and CTL containing 2,4,7-trinitro-9-fluorenone are laminated. (3) A structure in which CGL made of a berylene derivative and CTL containing an oxadiazole derivative are laminated (see US Pat. No. 3,871,882). (4) A structure in which CGL made of chlordiane blue or methylscalyllium and CTL containing a pyrazoline derivative are laminated (Japanese Patent Application Laid-Open No. 1977-
(See Publication No. 90827). (5) CGL made of amorphous selenium or its alloy;
A structure in which CTL containing a polyarylalkane-based aromatic amino compound is laminated (patent application)
52-147251 specification). (6) A structure in which CGL containing a perylene derivative and CTL containing a polyarylalkane aromatic amino compound are laminated (Patent application 1983-
19907 specification). As described above, many types of photosensitive layers are known, but in conventional electrophotographic photoreceptors having such photosensitive layers, the electricity of the photosensitive layer when repeatedly subjected to electrophotographic processes is limited. It has the disadvantage of severe mechanical fatigue and a very short service life. For example, when the electrophotographic photoreceptor is repeatedly subjected to an electrophotographic process, the potential history state of the electrophotographic photoreceptor is not maintained stably, making it impossible to obtain stable image forming characteristics. Furthermore, the use of specific bisazo compounds as CGM has been disclosed in, for example, JP-A-55-117151 and JP-A-54-145142.
Even in combination with CTM, which is said to be able to be combined with CGM, the above-mentioned drawbacks are still considerable. As can be understood from this, a carrier transport substance that is effective against a specific carrier generating substance is not always effective against other carrier generating substances, and Nor can it be said that effective carrier generating substances are always effective against other carrier transport substances. If the combination of both substances is inappropriate, not only will the electrophotographic sensitivity become low, but also the discharge efficiency will be poor especially at low electric fields, so the so-called residual potential will increase.
In the worst case, potential accumulates each time it is used repeatedly, making it practically unusable for electrophotographic purposes. In this way, there is no legal way to select a suitable combination of the constituent substances of the carrier generation phase and the constituent substances of the carrier transport phase, and it is necessary to practically determine an advantageous combination from among many substance groups. . The present invention comprises a photosensitive layer consisting of a combination of a carrier generation phase and a carrier transport phase, has high sensitivity, and maintains a stable potential history state even when repeatedly subjected to an electrophotographic process. An object of the present invention is to provide an electrophotographic photoreceptor that can form good visible images. The above object is to provide an electrophotographic photoreceptor in which a photosensitive layer comprising a combination of a carrier generation phase and a carrier transport phase is provided on a conductive support, wherein the carrier generation phase has the following general formula [] or general formula [' ]
This is achieved by an electrophotographic photoreceptor containing a bisazo compound represented by the following formula, wherein the carrier transport phase contains a carbazole derivative represented by the following general formula []. General formula [] General formula [′] [In the formula, Ar 1 , Ar 2 and Ar 3 are each a substituted or unsubstituted carbocyclic aromatic ring group, R 1 or R 2 is an electron-withdrawing group selected from a cyano group, a nitro group, or a halogen atom, respectively. , A:
【式】【formula】
【式】または[expression] or
【式】であつて、 X:ヒドロキシ基、[Formula], X: hydroxy group,
【式】または
―NHSO2―R6、
(但しR4およびR5はそれぞれ水素原子、置換、
未置換のアルキル基、R6は置換、未置換のアル
キル基もしくは置換、未置換のアリール基、)
Y:水素原子、ハロゲン原子、置換、未置換のア
ルキル基、アルコキシ基、カルボキシル基、
スルホ基、置換、未置換のカルバモイル基ま
たは置換、未置換のスルフアモイル基、(但
し、mが2以上のときは、互に異なる基であ
つてもよい。)
Z:置換、未置換の炭素環式芳香族環または置
換、未置換の複素環式芳香族環を構成するに
必要な原子群、
R3:水素原子、置換、未置換のアミノ基、置換、
未置換のカルバモイル基、カルボキシル基ま
たはそのエステル基、
A′:置換、未置換のアリール基、
n:1または2の整数、
m:0〜4の整数を表わす。〕
一般式〔〕
〔式中、
R7:置換、未置換のアリール基、
R8:水素原子、ハロゲン原子、置換、未置換の
アルキル基、アルコキシ基、アミノ基、置換
アミノ基、水酸基、
R9:置換、未置換のアリール基、置換、未置換
の複素環基を表わす。〕
前記一般式〔〕または一般式〔′〕で示さ
れるビスアゾ化合物のうち、好ましいのは次の一
般式〔a〕または一般式〔′a〕で示される
ものである。
一般式〔a〕
一般式〔′a〕
〔式中、
Ar1,Ar2,Ar3およびA:一般式〔〕または一
般式〔′〕において定義されたものと同じ
である。〕
更に好ましいものは、特に次の一般式〔b〕
または〔′b〕で示されるものである。
一般式〔b〕
一般式〔′b〕
式中、
A:一般式〔〕または一般式〔′〕において
定義されたものと同じ、
Ar4,Ar5およびAr6:置換、未置換のフエニル基
を表わし、置換基としては、メチル基、エチ
ル基などのアルキル基、メトキシ基、エトキ
シ基などのアルコキシ基、塩素原子、臭素原
子などのハロゲン原子、水酸基およびシアノ
基から選択されたものが好ましい。〕
即ち本発明においては、前記一般式〔〕また
は一般式〔′〕で示されるビスアゾ化合物を
CGMとして用いると共に、前記一般式〔〕で
示されるカルバゾール誘導体をCTMとして用い
てこれらを組合せることにより、キヤリアの発生
と輸送とをそれぞれ別個の物質で行なういわゆる
機能分離型感光体の感光層を構成する。そしてこ
のことにより、感度が大きく、しかも繰り返し電
子写真プロセスに供したときにも電位の履歴状態
が安定に維持され従つて常に良好な可視画像を形
成し得る電子写真感光体を提供することができ
る。
また本発明電子写真感光体においては、特に波
長600〜700nmの長波長域にも大きな分光感度が
得られ、従つて例えば波長6328Åのヘリウム―ネ
オンレーザを潜像形成用光源として用いることが
でき、更に低電界時におけるいわゆる電位の据切
れが良好で現像時に非画像部の電位が零またはこ
れに近い状態となるので、大きな実効バイアスを
得ることのできないトナーのみより成る一成分現
像剤によつても良好な現像を行なうことができ
る。
前記一般式〔〕で示されるビスアゾ化合物の
具体例としては、例えば次の構造式を有するもの
を挙げることができるが、これらに限定されるも
のではない。
例示化合物
前記一般式〔′〕で示されるビスアゾ化合物
の具体例としては、例えば次の構造式を有するも
のを挙げることができるが、これらに限定される
ものではない。
例示化合物
前記一般式〔〕で示されるカルバゾール誘導
体の具体例としては、例えば次の構造式を有する
ものを挙げることができるが、これらに限定され
るものではない。
例示化合物
次に本発明電子写真感光体の機械的構成につい
て説明する。
本発明の一例においては、第1図に示すよう
に、導電性支持体1上に既述のビスアゾ化合物を
主成分として含有して成るCGL2を形成し、こ
のCGL2上に既述のカルバゾール誘導体を主成
分として含有して成るCTL3を積層して形成し、
これらのCGL2とCTL3とにより感光層4を構
成する。
ここに前記導電性支持体1の材質としては、例
えばアルミニウム、ニツケル、銅、亜鉛、パラジ
ウム、銀、インジウム、錫、白金、金、ステンレ
ス鋼、真鍮等の金属のシートを用いることができ
る。しかしこれらに限定されるものではなく、例
えば第2図に示すように、絶縁性基体1A上に導
電層1Bを設けて導電性支持体1を構成せしめる
こともでき、この場合において基体1Aとしては
紙、プラスチツクシート等の可撓性を有し、しか
も曲げ、引張り等の応力に対して十分な強度を有
するものが適当である。又導電層1Bは金属シー
トをラミネートし或いは金属を真空蒸着せしめる
ことにより、又はその他の方法によつて設けるこ
とができる。
前記CGL2は、既述のビスアゾ化合物単独に
より、又はこれに適当なバインダー樹脂を加えた
ものにより、或いは更に特定又は非特定の極性の
キヤリアに対する移動度の大きい物質即ちCTM
を添加したものにより形成することができる。
具体的な方法としては、前記支持体上に、既述
のビスアゾ化合物を適当な溶剤に単独で或いは適
当なバインダー樹脂と共に溶解若しくは分散せし
めたものを塗布して乾燥せしめる方法が好便に利
用される。
この方法において、溶媒或いは分散媒として
は、例えばn―ブチルアミン、ジエチルアミン、
エチレンジアミン、イソプロパノールアミン、モ
ノエタノールアミン、トリエタノールアミン、ト
リエチレンジアミン、N,N―ジメチルホルムア
ミド、アセトン、メチルエチルケトン、シクロヘ
キサノン、ベンゼン、トルエン、キシレン、クロ
ロホルム、1,2―ジクロロエタン、ジクロロメ
タン、テトラヒドロフラン、ジオキサン、メタノ
ール、エタノール、イソプロパノール、酢酸エチ
ル、酢酸ブチル、ジメチルスルホキシド、その他
を用いることができる。
また、バインダー樹脂としては、例えばポリエ
チレン、ポリプロピレン、アクリル樹脂、メタク
リル樹脂、塩化ビニル樹脂、酢酸ビニル樹脂、エ
ポキシ樹脂、ポリウレタン樹脂、フエノール樹
脂、ポリエステル樹脂、アルキツド樹脂、ポリカ
ーボネート樹脂、シリコン樹脂、メラミン樹脂等
の付加重合型樹脂、重付加型樹脂、重縮合型樹
脂、並びにこれらの樹脂の繰り返し単位のうちの
2つ以上を含む共重合体樹脂、例えば塩化ビニル
―酢酸ビニル共重合体樹脂、塩化ビニル―酢酸ビ
ニル―無水マレイン酸共重合体樹脂等の絶縁性樹
脂の他、ポリ―N―ビニルカルバゾール等の高分
子有機半導体を挙げることができる。そして、こ
のバインダー樹脂のビスアゾ化合物に対する割合
は、0〜100重量%、特に0〜10重量%の範囲で
ある。
前記CGL2には、必要に応じて適宜のCTMを
添加してもよい。
以上のようにして形成される前記CGL2の厚
さは、好ましくは0.005〜20ミクロン、特に好ま
しくは0.05〜5ミクロンである。0.005ミクロン
未満では充分な光感度が得られず、また20ミクロ
ンを越えると充分な電荷保持性が得られない。
また前記CTL3は、既述のカルバゾール誘導
体により、上述のCGL2と同様にして、即ち単
独で或いはバインダー樹脂と共に形成することが
できる。そして、他のCTMを含有せしめてもよ
い。このCTL3の厚さは2〜100ミクロン、好ま
しくは5〜30ミクロンである。
本発明電子写真感光体は、他の機械的構成とす
ることができる。例えば第3図に示すように、導
電性支持体1上に適当な中間層5を設け、これを
介してCGL2を形成し、このCGL2上にCTL3
を形成するようにしてもよい。この中間層5に
は、感光層4の帯電時において導電性支持体1か
ら感光層4にフリーキヤリアが注入されることを
阻止する機能、或いは感光層4を導電性支持体に
対して一体的に接着せしめる接着層としての機能
を有せしめることができる。斯かる中間層5の材
質としては、酸化アルミニウム、酸化インジウム
等の金属酸化物、アクリル樹脂、メタクリル樹
脂、塩化ビニル樹脂、酢酸ビニル樹脂、エポキシ
樹脂、ポリウレタン樹脂、フエノール樹脂ポリエ
ステル樹脂、アルキツド樹脂、ポリカーボネート
樹脂、シリコン樹脂、メラミン樹脂、塩化ビニル
―酢酸ビニル共重合体樹脂、塩化ビニル―酢酸ビ
ニル―無水マレイン酸共重合体樹脂等の高分子物
質を用いることができる。
又第4図に示すように、導電性支持体1上に、
前記中間層5を介して又は介さずに、CTL3を
形成し、このCTL3上にCGL2を形成して感光
層4を構成せしめてもよい。
更に、既述のビスアゾ化合物を、既述のカルバ
ゾール誘導体が含有されたキヤリア輸送相中に分
散含有せしめてキヤリア発生相を形成し、単一層
状の感光層を形成することも可能である。
なお、本発明における感光層を構成する層に
は、必要に応じて種々の添加剤を加えることがで
きる。
以下本発明の実施例について説明するが、これ
らによつて本発明が限定されるものではない。
実施例 1
アルミニウムを蒸着した厚さ100ミクロンのポ
リエチレンテレフタレートより成る導電性支持体
上に、塩化ビニル―酢酸ビニル―無水マレイン酸
共重合体「エスレツクMF―10」(積水化学工業
社製)より成る厚さ約0.05ミクロンの中間層を設
け、例示化合物(―16)で示したビスアゾ化合
物1.5gを1,2―ジクロルエタン100mlと共に8
時間ボールミルにより分解し、ここに得られた分
散液を前記中間層上にドクターブレードを用いて
塗布し、十分乾燥して厚さ約0.5ミクロンのCGL
を形成した。
一方、例示化合物(―16)で示したカルバゾ
ール誘導体11.25gとポリカーボネート樹脂「パ
ンライトL―1250」(帝人化成社製)15gとを1,
2―ジクロルエタン100mlに溶解し、得られた溶
液を前記CGL上にドクターブレードを用いて塗
布し、十分乾燥して厚さ12ミクロンのCTLを形
成し、以つて本発明電子写真感光体を製造した。
これを「試料1」とする。
実施例 2〜8
CGLの形及びCTLの形成において、例示化合
物として下記第1表に示す組合せのものを用いた
他は実施例1と同様にして7種の本発明電子写真
感光体を製造した。これらをそれぞれ「試料2」
〜「試料8」とする。[Formula] or -NHSO 2 -R 6 , (where R 4 and R 5 are hydrogen atoms, substitutions,
unsubstituted alkyl group, R 6 is a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group,) Y: hydrogen atom, halogen atom, substituted or unsubstituted alkyl group, alkoxy group, carboxyl group,
Sulfo group, substituted or unsubstituted carbamoyl group, substituted or unsubstituted sulfamoyl group, (However, when m is 2 or more, mutually different groups may be used.) Z: Substituted or unsubstituted carbon ring Atom group necessary to constitute an aromatic ring or a substituted or unsubstituted heterocyclic aromatic ring, R 3 : hydrogen atom, substituted or unsubstituted amino group, substituted,
An unsubstituted carbamoyl group, a carboxyl group or an ester group thereof, A': a substituted or unsubstituted aryl group, n: an integer of 1 or 2, m: an integer of 0 to 4. ] General formula [ ] [In the formula, R 7 : substituted or unsubstituted aryl group, R 8 : hydrogen atom, halogen atom, substituted or unsubstituted alkyl group, alkoxy group, amino group, substituted amino group, hydroxyl group, R 9 : substituted or unsubstituted Represents a substituted aryl group, substituted or unsubstituted heterocyclic group. ] Among the bisazo compounds represented by the general formula [] or ['], preferred are those represented by the following general formula [a] or ['a]. General formula [a] General formula ['a] [In the formula, Ar 1 , Ar 2 , Ar 3 and A: the same as defined in the general formula [] or the general formula [′]. ] More preferable ones are particularly the following general formula [b]
or ['b]. General formula [b] General formula ['b] In the formula, A: the same as defined in general formula [] or general formula ['], Ar 4 , Ar 5 and Ar 6 represent substituted or unsubstituted phenyl groups, and the substituents include methyl group, Those selected from alkyl groups such as ethyl groups, alkoxy groups such as methoxy groups and ethoxy groups, halogen atoms such as chlorine atoms and bromine atoms, hydroxyl groups and cyano groups are preferred. ] That is, in the present invention, the bisazo compound represented by the above general formula [ ] or general formula ['] is
By using the carbazole derivative represented by the above general formula [] as a CGM and combining these as a CTM, a photosensitive layer of a so-called functionally separated photoreceptor in which carrier generation and transport are performed by separate substances, respectively, can be created. Configure. As a result, it is possible to provide an electrophotographic photoreceptor that has high sensitivity, maintains a stable potential history state even when subjected to repeated electrophotographic processes, and can therefore always form good visible images. . Further, in the electrophotographic photoreceptor of the present invention, a large spectral sensitivity can be obtained especially in the long wavelength range of 600 to 700 nm, and therefore, for example, a helium-neon laser with a wavelength of 6328 Å can be used as a light source for forming a latent image. Furthermore, when the electric field is low, the so-called potential termination is good, and the potential of the non-image area becomes zero or close to zero during development, so it is impossible to obtain a large effective bias using a one-component developer made only of toner. It is also possible to perform good development. Specific examples of the bisazo compound represented by the general formula [] include those having the following structural formula, but are not limited thereto. Exemplary compound Specific examples of the bisazo compound represented by the general formula ['] include those having the following structural formula, but are not limited thereto. Exemplary compound Specific examples of the carbazole derivative represented by the general formula [] include those having the following structural formula, but are not limited thereto. Exemplary compound Next, the mechanical structure of the electrophotographic photoreceptor of the present invention will be explained. In one example of the present invention, as shown in FIG. 1, CGL 2 containing the above-mentioned bisazo compound as a main component is formed on a conductive support 1, and the above-mentioned carbazole derivative is formed on this CGL 2. Formed by laminating CTL3 containing as the main component,
These CGL2 and CTL3 constitute a photosensitive layer 4. Here, as the material of the conductive support 1, for example, a sheet of metal such as aluminum, nickel, copper, zinc, palladium, silver, indium, tin, platinum, gold, stainless steel, or brass can be used. However, the invention is not limited to these. For example, as shown in FIG. 2, a conductive layer 1B may be provided on an insulating substrate 1A to constitute the conductive support 1. In this case, the substrate 1A may be Suitable materials include paper, plastic sheets, and other materials that are flexible and have sufficient strength against stress such as bending and tension. The conductive layer 1B can also be provided by laminating metal sheets, vacuum depositing metal, or by other methods. The above-mentioned CGL2 can be prepared by using the above-mentioned bisazo compound alone, by adding a suitable binder resin to it, or by adding a substance having high mobility to a specific or non-specific polar carrier, that is, CTM.
It can be formed by adding . As a specific method, a method is conveniently used in which the above-mentioned bisazo compound is dissolved or dispersed in a suitable solvent or dissolved or dispersed together with a suitable binder resin and then applied onto the support and dried. Ru. In this method, examples of the solvent or dispersion medium include n-butylamine, diethylamine,
Ethylenediamine, isopropanolamine, monoethanolamine, triethanolamine, triethylenediamine, N,N-dimethylformamide, acetone, methyl ethyl ketone, cyclohexanone, benzene, toluene, xylene, chloroform, 1,2-dichloroethane, dichloromethane, tetrahydrofuran, dioxane, methanol , ethanol, isopropanol, ethyl acetate, butyl acetate, dimethyl sulfoxide, and others can be used. Examples of binder resins include polyethylene, polypropylene, acrylic resin, methacrylic resin, vinyl chloride resin, vinyl acetate resin, epoxy resin, polyurethane resin, phenolic resin, polyester resin, alkyd resin, polycarbonate resin, silicone resin, melamine resin, etc. addition polymerization type resins, polyaddition type resins, polycondensation type resins, and copolymer resins containing two or more of the repeating units of these resins, such as vinyl chloride-vinyl acetate copolymer resins, vinyl chloride- In addition to insulating resins such as vinyl acetate-maleic anhydride copolymer resins, polymeric organic semiconductors such as poly-N-vinylcarbazole can be used. The ratio of this binder resin to the bisazo compound is in the range of 0 to 100% by weight, particularly 0 to 10% by weight. An appropriate CTM may be added to the CGL2 as necessary. The thickness of the CGL 2 formed as described above is preferably 0.005 to 20 microns, particularly preferably 0.05 to 5 microns. If it is less than 0.005 microns, sufficient photosensitivity cannot be obtained, and if it exceeds 20 microns, sufficient charge retention cannot be obtained. Further, the CTL3 can be formed using the above-mentioned carbazole derivative in the same manner as the above-mentioned CGL2, that is, alone or together with a binder resin. Further, other CTMs may be included. The thickness of this CTL 3 is between 2 and 100 microns, preferably between 5 and 30 microns. The electrophotographic photoreceptor of the present invention may have other mechanical configurations. For example, as shown in FIG. 3, a suitable intermediate layer 5 is provided on a conductive support 1, a CGL 2 is formed through this, and a CTL 3 is formed on this CGL 2.
may be formed. This intermediate layer 5 has a function of preventing free carriers from being injected from the conductive support 1 into the photosensitive layer 4 when the photosensitive layer 4 is charged, or a function of preventing the photosensitive layer 4 from being integrally connected to the conductive support. It can function as an adhesive layer for adhering to. Materials for the intermediate layer 5 include metal oxides such as aluminum oxide and indium oxide, acrylic resins, methacrylic resins, vinyl chloride resins, vinyl acetate resins, epoxy resins, polyurethane resins, phenolic resins, polyester resins, alkyd resins, and polycarbonates. Polymeric substances such as resin, silicone resin, melamine resin, vinyl chloride-vinyl acetate copolymer resin, vinyl chloride-vinyl acetate-maleic anhydride copolymer resin, etc. can be used. Moreover, as shown in FIG. 4, on the conductive support 1,
The photosensitive layer 4 may be constructed by forming the CTL 3 with or without the intermediate layer 5 and forming the CGL 2 on the CTL 3. Furthermore, it is also possible to form a single-layer photosensitive layer by dispersing the above-mentioned bisazo compound in a carrier transport phase containing the above-mentioned carbazole derivative to form a carrier generation phase. In addition, various additives can be added to the layer constituting the photosensitive layer in the present invention, if necessary. Examples of the present invention will be described below, but the present invention is not limited thereto. Example 1 A conductive support made of polyethylene terephthalate with a thickness of 100 microns on which aluminum was vapor-deposited was coated with vinyl chloride-vinyl acetate-maleic anhydride copolymer "Eslec MF-10" (manufactured by Sekisui Chemical Co., Ltd.). An intermediate layer with a thickness of approximately 0.05 microns was provided, and 1.5 g of the bisazo compound shown as exemplified compound (-16) was added to the
The resulting dispersion was coated on the intermediate layer using a doctor blade and dried sufficiently to form a CGL with a thickness of about 0.5 microns.
was formed. On the other hand, 11.25 g of the carbazole derivative shown as exemplified compound (-16) and 15 g of polycarbonate resin "Panlite L-1250" (manufactured by Teijin Kasei) were mixed in 1,
It was dissolved in 100 ml of 2-dichloroethane, and the resulting solution was applied onto the CGL using a doctor blade and sufficiently dried to form a CTL with a thickness of 12 microns, thereby producing an electrophotographic photoreceptor of the present invention. .
This will be referred to as "Sample 1". Examples 2 to 8 Seven types of electrophotographic photoreceptors of the present invention were manufactured in the same manner as in Example 1, except that the combinations shown in Table 1 below were used as exemplary compounds in the formation of CGL and CTL. . These are each called “Sample 2”
~ "Sample 8".
【表】【table】
【表】
実施例 9
実施例1におけると同様にして導電性支持体上
に中間層を設け、例示化合物(――16)で示し
たビスアゾ化合物の1.5gとポリカーボネート樹
脂「パンライトL―1250」の15gとを1,2―ジ
クロルエタン100mlに加えて12時間ボールミルに
より分散を行ない、得られた分散液を前記中間層
上にドクタープレードにより塗布し、十分乾燥さ
せて厚さ約1ミクロンのCGLを形成した。
このCGL上に、実施例1におけると同様にし
てCTLを形成し、以つて本発明電子写真感光体
を製造した。これを「試料9」とする。
実施例 10
CGLの形成において、ビスアゾ化合物として
例示化合物(′―5)で示したものを用い、
CTLの形成において、カルバゾール誘導体とし
て例示化合物(―31)で示したものを用いたほ
かは実施例9と全く同様にして本発明電子写真感
光体を製造した。これを「試料10」とする。
比較例 1
実施例1のCTLの形成において、カルバゾー
ル誘導体の代りに次の構造式を有するピラゾリン
誘導体を用いたほかは、実施例1と同様にして比
較用電子写真感光体を製造した。これを「比較試
料1」とする。
比較例 2
実施例1のCTLの形成において、カルバゾー
ル誘導体の代りに次の構造式を有するオキサジア
ゾール誘導体を用いたほかは、実施例1と同様に
して比較用電子写真感光体を製造した。これを
「比較試料2」とする。
以上のようにして得られた電子写真感光体、試
料1〜試料10並びに比較試料1及び比較試料2の
各々について、「エレクトロメーターSP―428型」
(川口電機製作所製)を用いて、その電子写真特
性を調べた。即ち感光体表面を帯電電圧−6KV
で5秒間帯電させた時の受容電位VA(V)と、5
秒間暗減衰させた後の電位VI(初期電位)を1/2
に減衰させるために必要な露光量E1/2(lux・
秒)、更に暗減衰率(VA−VI)/VA×100(%)
とを調べた。結果は第2表に示す通りである。[Table] Example 9 An intermediate layer was provided on a conductive support in the same manner as in Example 1, and 1.5 g of the bisazo compound shown as exemplified compound (--16) and polycarbonate resin "Panlite L-1250" were added. Add 15 g of 1,2-dichloroethane to 100 ml of 1,2-dichloroethane and disperse using a ball mill for 12 hours. The resulting dispersion was applied onto the intermediate layer using a doctor blade and thoroughly dried to form a CGL with a thickness of about 1 micron. Formed. CTL was formed on this CGL in the same manner as in Example 1, thereby producing an electrophotographic photoreceptor of the present invention. This will be referred to as "Sample 9." Example 10 In the formation of CGL, the bisazo compound shown in exemplified compound ('-5) was used,
An electrophotographic photoreceptor of the present invention was produced in exactly the same manner as in Example 9, except that the carbazole derivative shown in exemplified compound (-31) was used in the formation of CTL. This will be referred to as "Sample 10." Comparative Example 1 A comparative electrophotographic photoreceptor was produced in the same manner as in Example 1, except that a pyrazoline derivative having the following structural formula was used in place of the carbazole derivative in the formation of CTL in Example 1. This is referred to as "comparative sample 1." Comparative Example 2 A comparative electrophotographic photoreceptor was produced in the same manner as in Example 1, except that an oxadiazole derivative having the following structural formula was used in place of the carbazole derivative in the formation of CTL in Example 1. This will be referred to as "comparative sample 2." For each of the electrophotographic photoreceptors obtained as described above, Samples 1 to 10, Comparative Sample 1, and Comparative Sample 2, "Electrometer SP-428 Model" was used.
(manufactured by Kawaguchi Electric Seisakusho) to investigate its electrophotographic properties. In other words, the surface of the photoreceptor is charged with a voltage of -6KV.
The acceptance potential V A (V) when charged for 5 seconds at 5
The potential V I (initial potential) after dark decay for seconds is 1/2
The exposure amount E1/2 (lux・
seconds), and dark decay rate (V A − V I )/V A ×100 (%)
I looked into it. The results are shown in Table 2.
【表】【table】
【表】
この第2表の結果より、本発明電子写真感光体
は大きな感度を有するものであることが明かであ
る。
また試料1〜試料10並びに比較試料1と比較試
料2の各々を乾式電子複写機「U―Bix2000R」
(小西六写真工業社製)に装着して連続複写を行
ない、露光絞り値1.0における黒紙電位Vb(V)及
び白紙電位VW(V)を「エレクトロスタチツクボ
ルトメーター144D―1D型」(モンローエレクト
ロニクスインコーポレーテツド製)を用い、現像
する直前において測定した。結果は第3表に示す
通りである。
尚ここでいう黒紙電位とは反射濃度1.3の黒紙
を原稿とし、上述の複写サイクルを実施したとき
の感光体の表面電位を表わし、白紙電位とは白紙
を原稿としたときの感光体の表面電位を表わす。[Table] From the results in Table 2, it is clear that the electrophotographic photoreceptor of the present invention has high sensitivity. In addition, each of Samples 1 to 10, Comparative Sample 1 and Comparative Sample 2 was transferred using a dry electronic copying machine "U-Bix2000R".
(manufactured by Konishiroku Photo Industry Co., Ltd.) to perform continuous copying, and measure the black paper potential V b (V) and white paper potential V W (V) at an exposure aperture value of 1.0 using an "electrostatic voltmeter 144D-1D model". (manufactured by Monroe Electronics, Inc.) and was measured immediately before development. The results are shown in Table 3. The black paper potential here refers to the surface potential of the photoreceptor when the above-mentioned copying cycle is performed using black paper with a reflection density of 1.3 as the original, and the white paper potential refers to the surface potential of the photoreceptor when the original is a blank paper. Represents surface potential.
【表】【table】
【表】
この第3表の結果から明かなように、本発明電
子写真感光体は、繰り返し電子写真プロセスに供
したときにも電位の履歴状態が安定に維持され、
良好な画質の可視画像を多数安定に形成すること
ができる。[Table] As is clear from the results in Table 3, the electrophotographic photoreceptor of the present invention maintains a stable potential history state even when subjected to repeated electrophotographic processes.
A large number of visible images of good quality can be stably formed.
第1図は本発明電子写真感光体の構成の一例を
示す説明用断面図、第2図は本発明電子写真感光
体の他の構成例を示す説明用断面図、第3図及び
第4図はそれぞれ本発明電子写真感光体の更に他
の構成例を示す説明用断面図である。
1…導電性支持体、2…キヤリア発生層
(CGL)、3…キヤリア輸送層(CTL)、4…感光
層、5…中間層、1A…絶縁性基体、1B…導電
層。
FIG. 1 is an explanatory sectional view showing an example of the structure of the electrophotographic photoreceptor of the present invention, FIG. 2 is an explanatory sectional view showing another example of the structure of the electrophotographic photoreceptor of the invention, and FIGS. 3 and 4 2A and 2B are explanatory cross-sectional views showing still other structural examples of the electrophotographic photoreceptor of the present invention. DESCRIPTION OF SYMBOLS 1... Conductive support, 2... Carrier generation layer (CGL), 3... Carrier transport layer (CTL), 4... Photosensitive layer, 5... Intermediate layer, 1A... Insulating substrate, 1B... Conductive layer.
Claims (1)
て成る感光層を導電性支持体上に設けて成る電子
写真感光体において、前記キヤリア発生相が下記
一般式〔〕または一般式〔′〕で示されるビ
スアゾ化合物を含有し、前記キヤリア輸送相が下
記一般式〔〕で示されるカルバゾール誘導体を
含有することを特徴とする電子写真感光体。 一般式〔〕 一般式〔′〕 〔式中、 Ar1,Ar2およびAr3: それぞれ置換、未置換の炭素環式芳香族環
基、 R1またはR2: それぞれシアノ基、ニトロ基、ハロゲン原子
より選ばれた電子吸引性基、 A:【式】【式】 【式】【式】または 【式】であつて、 X:ヒドロキシ基、【式】または ―NHSO2―R6、 [但しR4およびR5はそれぞれ水素原子、置換、
未置換のアルキル基、R6は置換、未置換のアル
キル基もしくは置換、未置換のアリール基、] Y:水素原子、ハロゲン原子、置換、未置換のア
ルキル基、アルコキシ基、カルボキシル基、
スルホ基、置換、未置換のカルバモイル基ま
たは置換、未置換のスルフアモイル基、(但
し、mが2以上のときは、互に異なる基であ
つてもよい。) Z:置換、未置換の炭素環式芳香族環または置
換、未置換の複素環式芳香族環を構成するに
必要な原子群、 R3:水素原子、置換、未置換のアミノ基、置換、
未置換のカルバモイル基、カルボキシル基ま
たはそのエステル基、 A′:置換、未置換のアリール基、 n:1または2の整数、 m:0〜4の整数を表わす。〕 一般式〔〕 〔式中、 R7:置換、未置換のアリール基、 R8:水素原子、ハロゲン原子、置換、未置換の
アルキル基、アルコキシ基、アミノ基、置換
アミノ基、水酸基、 R9:置換、未置換のアリール基、置換、未置換
の複素環基を表わす。〕[Scope of Claims] 1. An electrophotographic photoreceptor in which a photosensitive layer comprising a combination of a carrier generation phase and a carrier transport phase is provided on a conductive support, wherein the carrier generation phase has the following general formula [] or the general formula An electrophotographic photoreceptor comprising a bisazo compound represented by ['], wherein the carrier transport phase contains a carbazole derivative represented by the following general formula []. General formula [] General formula [′] [In the formula, Ar 1 , Ar 2 and Ar 3 are each a substituted or unsubstituted carbocyclic aromatic ring group, R 1 or R 2 is an electron-withdrawing group selected from a cyano group, a nitro group, or a halogen atom, respectively. , A: [Formula] [Formula] [Formula] [Formula] or [Formula], where X: hydroxy group, [Formula] or -NHSO 2 -R 6 , [However, R 4 and R 5 are each a hydrogen atom , replacement,
unsubstituted alkyl group, R 6 is a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group, ] Y: hydrogen atom, halogen atom, substituted or unsubstituted alkyl group, alkoxy group, carboxyl group,
Sulfo group, substituted or unsubstituted carbamoyl group, substituted or unsubstituted sulfamoyl group, (However, when m is 2 or more, mutually different groups may be used.) Z: Substituted or unsubstituted carbon ring Atom group necessary to constitute an aromatic ring or a substituted or unsubstituted heterocyclic aromatic ring, R 3 : hydrogen atom, substituted or unsubstituted amino group, substituted,
An unsubstituted carbamoyl group, a carboxyl group or an ester group thereof, A': a substituted or unsubstituted aryl group, n: an integer of 1 or 2, m: an integer of 0 to 4. ] General formula [ ] [In the formula, R 7 : substituted or unsubstituted aryl group, R 8 : hydrogen atom, halogen atom, substituted or unsubstituted alkyl group, alkoxy group, amino group, substituted amino group, hydroxyl group, R 9 : substituted or unsubstituted Represents a substituted aryl group, substituted or unsubstituted heterocyclic group. ]
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP57214037A JPS59104656A (en) | 1982-12-08 | 1982-12-08 | Electrophotographic sensitive body |
US06/549,601 US4540651A (en) | 1982-11-10 | 1983-11-07 | Electrophotographic photosensitive member |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP57214037A JPS59104656A (en) | 1982-12-08 | 1982-12-08 | Electrophotographic sensitive body |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS59104656A JPS59104656A (en) | 1984-06-16 |
JPH0118417B2 true JPH0118417B2 (en) | 1989-04-05 |
Family
ID=16649226
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP57214037A Granted JPS59104656A (en) | 1982-11-10 | 1982-12-08 | Electrophotographic sensitive body |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS59104656A (en) |
-
1982
- 1982-12-08 JP JP57214037A patent/JPS59104656A/en active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS59104656A (en) | 1984-06-16 |
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