JPH0513514B2 - - Google Patents
Info
- Publication number
- JPH0513514B2 JPH0513514B2 JP20033285A JP20033285A JPH0513514B2 JP H0513514 B2 JPH0513514 B2 JP H0513514B2 JP 20033285 A JP20033285 A JP 20033285A JP 20033285 A JP20033285 A JP 20033285A JP H0513514 B2 JPH0513514 B2 JP H0513514B2
- Authority
- JP
- Japan
- Prior art keywords
- electrophotographic
- present
- compound
- substituted
- resin
- 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 - Fee Related
Links
- 239000000463 material Substances 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 150000001450 anions Chemical class 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 2
- -1 pyrylium compound Chemical class 0.000 description 20
- 229920005989 resin Polymers 0.000 description 19
- 239000011347 resin Substances 0.000 description 19
- 239000010408 film Substances 0.000 description 14
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- 229920000642 polymer Polymers 0.000 description 10
- 230000035945 sensitivity Effects 0.000 description 10
- 238000010521 absorption reaction Methods 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 239000010410 layer Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 239000010419 fine particle Substances 0.000 description 6
- 239000004065 semiconductor Substances 0.000 description 6
- 239000011230 binding agent Substances 0.000 description 5
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 5
- 229920000728 polyester Polymers 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 230000010355 oscillation Effects 0.000 description 4
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical group C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- RYAQAOLNUHTJAJ-UHFFFAOYSA-N 2,6-ditert-butyl-4-methylpyrylium Chemical class CC1=CC(C(C)(C)C)=[O+]C(C(C)(C)C)=C1 RYAQAOLNUHTJAJ-UHFFFAOYSA-N 0.000 description 3
- HFQYMLFZIPPAHH-UHFFFAOYSA-N 4-methyl-2,6-diphenylpyrylium Chemical class C=1C(C)=CC(C=2C=CC=CC=2)=[O+]C=1C1=CC=CC=C1 HFQYMLFZIPPAHH-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 239000004952 Polyamide Substances 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 230000014759 maintenance of location Effects 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- ZFYNTCNECVPHDZ-UHFFFAOYSA-N n-(3-phenyliminoprop-1-enyl)aniline Chemical compound C=1C=CC=CC=1NC=CC=NC1=CC=CC=C1 ZFYNTCNECVPHDZ-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 108091008695 photoreceptors Proteins 0.000 description 3
- 239000004014 plasticizer Substances 0.000 description 3
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 3
- 229920002647 polyamide Polymers 0.000 description 3
- 239000011241 protective layer Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 229910006404 SnO 2 Inorganic materials 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-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
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 229920002492 poly(sulfone) Polymers 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 230000001235 sensitizing effect Effects 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 description 1
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- ZXBSSAFKXWFUMF-UHFFFAOYSA-N 1,2,3-trinitrofluoren-9-one Chemical compound C12=CC=CC=C2C(=O)C2=C1C=C([N+](=O)[O-])C([N+]([O-])=O)=C2[N+]([O-])=O ZXBSSAFKXWFUMF-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- VERMWGQSKPXSPZ-BUHFOSPRSA-N 1-[(e)-2-phenylethenyl]anthracene Chemical class C=1C=CC2=CC3=CC=CC=C3C=C2C=1\C=C\C1=CC=CC=C1 VERMWGQSKPXSPZ-BUHFOSPRSA-N 0.000 description 1
- KXJGSNRAQWDDJT-UHFFFAOYSA-N 1-acetyl-5-bromo-2h-indol-3-one Chemical compound BrC1=CC=C2N(C(=O)C)CC(=O)C2=C1 KXJGSNRAQWDDJT-UHFFFAOYSA-N 0.000 description 1
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 1
- JIQXGYXUYOSMTP-UHFFFAOYSA-M 2,6-diphenyl-3-propylpyrylium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.CCCC1=CC=C(C=2C=CC=CC=2)[O+]=C1C1=CC=CC=C1 JIQXGYXUYOSMTP-UHFFFAOYSA-M 0.000 description 1
- AOPZJMHAPGXPAP-UHFFFAOYSA-M 2,6-ditert-butyl-4-ethylpyrylium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.CCC1=CC(C(C)(C)C)=[O+]C(C(C)(C)C)=C1 AOPZJMHAPGXPAP-UHFFFAOYSA-M 0.000 description 1
- QXNSLVNOCIVYIO-UHFFFAOYSA-M 2,6-ditert-butyl-4-methylpyrylium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.CC1=CC(C(C)(C)C)=[O+]C(C(C)(C)C)=C1 QXNSLVNOCIVYIO-UHFFFAOYSA-M 0.000 description 1
- GQHQUFLPSBUAEO-UHFFFAOYSA-N 2-(5-phenyl-1,3-oxazol-2-yl)aniline Chemical compound NC1=CC=CC=C1C1=NC=C(C=2C=CC=CC=2)O1 GQHQUFLPSBUAEO-UHFFFAOYSA-N 0.000 description 1
- WGRSVHBSCVGKDP-UHFFFAOYSA-N 2-ethyl-9h-carbazole-1-carbaldehyde Chemical compound C1=CC=C2C3=CC=C(CC)C(C=O)=C3NC2=C1 WGRSVHBSCVGKDP-UHFFFAOYSA-N 0.000 description 1
- IBDCHGJXDLAGGO-UHFFFAOYSA-M 4-methyl-2,6-diphenylpyrylium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.C=1C(C)=CC(C=2C=CC=CC=2)=[O+]C=1C1=CC=CC=C1 IBDCHGJXDLAGGO-UHFFFAOYSA-M 0.000 description 1
- FMJYAHOTKMLFFD-UHFFFAOYSA-M 4-methylpyrylium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.CC1=CC=[O+]C=C1 FMJYAHOTKMLFFD-UHFFFAOYSA-M 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 229910052582 BN Inorganic materials 0.000 description 1
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- 229920000459 Nitrile rubber Polymers 0.000 description 1
- 239000002033 PVDF binder Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-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
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
- 229920006243 acrylic copolymer Polymers 0.000 description 1
- 229920006222 acrylic ester polymer Polymers 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 230000002238 attenuated effect Effects 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical class C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 229910000416 bismuth oxide Inorganic materials 0.000 description 1
- 229920000402 bisphenol A polycarbonate polymer Polymers 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 125000005997 bromomethyl group Chemical group 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- TYIXMATWDRGMPF-UHFFFAOYSA-N dibismuth;oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Bi+3].[Bi+3] TYIXMATWDRGMPF-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 150000008376 fluorenones Chemical class 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- 125000001207 fluorophenyl group Chemical group 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229940083761 high-ceiling diuretics pyrazolone derivative Drugs 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 150000007978 oxazole derivatives Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000570 polyether Polymers 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
- 229920001721 polyimide Polymers 0.000 description 1
- 229920001470 polyketone Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- RCYFOPUXRMOLQM-UHFFFAOYSA-N pyrene-1-carbaldehyde Chemical compound C1=C2C(C=O)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 RCYFOPUXRMOLQM-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 229910001112 rose gold Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- WRTMQOHKMFDUKX-UHFFFAOYSA-N triiodide Chemical compound I[I-]I WRTMQOHKMFDUKX-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229940098697 zinc laurate Drugs 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- GPYYEEJOMCKTPR-UHFFFAOYSA-L zinc;dodecanoate Chemical compound [Zn+2].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O GPYYEEJOMCKTPR-UHFFFAOYSA-L 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
- G03G5/0664—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
- G03G5/05—Organic bonding materials; Methods for coating a substrate with a photoconductive layer; Inert supplements for use in photoconductive layers
- G03G5/0503—Inert supplements
- G03G5/051—Organic non-macromolecular compounds
- G03G5/0514—Organic non-macromolecular compounds not comprising cyclic 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
- G03G5/05—Organic bonding materials; Methods for coating a substrate with a photoconductive layer; Inert supplements for use in photoconductive layers
- G03G5/0503—Inert supplements
- G03G5/051—Organic non-macromolecular compounds
- G03G5/0521—Organic non-macromolecular compounds comprising one or more heterocyclic groups
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Photoreceptors In Electrophotography (AREA)
Description
「産業上の利用分野」
本考案は有機光導電性物質を主体とした高感度
な電子写真感光材料、特に半導体レーザーの波長
領域において高感度を示す電子写真感光材料に関
する。
「従来の技術」
近年半導体レーザーを光源とした電子写真シス
テムが盛んに開発されている。半導体レーザーは
He−Ne等のガスレーザーに比べて小型かつ低コ
ストであり、直接変調が可能なこと等大きな利点
を有しているが、発振波長が750nm以上となるこ
とが多かつた。従つてこのシステムに用いる感光
体は750nm以上に吸収を持ち、高感度を示す必要
があり、各種の増感染料等の開発が行われてい
る。ところが一般にこのような長波長域に吸収を
持つ有機化合物は熱交換器や湿度に対して不安定
なものが多く、製造上、取り扱い上問題があり、
さらにはそれらを用いて作製した感光材料は経時
変化が著しく、長期間保存すると感光体としての
機能を失つてしまうものが多かつた。
またこのような波長域に主吸収をもつていても
吸光係数が小さかつたり、低い電子写真感度しか
示さないものもあり、現状は必ずしも満足すべき
状態ではなく、さらに高感度、高耐久性を示す電
子写真感光体の開発が望まれている。
「発明が解決しようとする問題点」
本発明の第一の目的は有機光導電性物質とピリ
リウム化合物を含み、高い感度を有する電子写真
感光材料を提供することにある。
本発明の第二の目的は熱や湿度に対して耐久性
のある電子写真感光材料を提供することにある。
本発明の第三の目的は半導体レーザーの発振波
長領域に主吸収を有し、高感度を示す電子写真感
光材料を提供することにある。
「問題点を解決するための手段」
即ち本発明者らは鋭意研究の結果下記一般式
（）で示される化合物を少くとも一種含有した
電子写真感光材料を作製することにより上記問題
点を解決することができた。
一般式（）
式中、R1、R2、R4、R5は水素原子、置換もし
くは未置換のアルキル基、置換もしくは未置換の
アリール基を示し、R3は水素原子、ハロゲン原
子、置換もしくは未置換のアルキル基、置換もし
くは未置換のアリール基を示す。R1、R2、R3、
R4、R5の水素原子、アリール基はそれぞれ同じ
ものでも異つていてもよい。Ｘはアニオンを示
す。
なお、R1、R2、R3、R4、R5の好ましいアルキ
ル基は、炭素原子数１〜18個のアルキル基であ
り、具体的にはメチル、エチル、ｎ−プロピル、
iso−プロピル、ｎ−ブチル、sec−ブチル、tert
−ブチル、ｎ−アミル、ｎ−ヘキシル、ｎ−ヘプ
チル、ｎ−ノニル、ｎ−ドデシル、２−エチルヘ
キシル、フルオロメチル、クロロメチル、ブロモ
メチル、トリフルオロメチル、メトキシメチル、
シアノメチル、アルキルチオメチル等が挙げられ
る。
また好ましいアリール基は、炭素原子数６〜24
個までのアリール基であり、具体的にはフエニ
ル、トリル、クロロフエニル、フルオロフエニ
ル、ナフチル等が挙げられる。
またＸのアニオンの具体例としてはパークロレ
ート、テトラフルオロボレート、アイオダイド、
クロライド、ブロミド、サルフエート、パーアイ
オダイド、ｐ−トルエンスルホネート等が挙げら
れる。
本発明に用いられる化合物において、一方のピ
リリウム環に導入されているtert−ブチル基（以
下、tert−Bu基で記す）は化合物の安定性を向
上させかつ溶解性を向上させる役割を荷つてい
る。もう一方のピリリウム環に導入されているフ
エニル基（以下、φ−基で記す）は主吸収を
780nm付近へ設定するためのものである。R1〜
R5は吸収極大波長を所望に応じて微調整する役
割を持つ。
次に一般式（）で示される本発明に用いる化
合物の代表例を下記に示すが本発明はこれによつ
て限定されるものではない。
本発明に使用するピリリウ系化合物は有機光導
電体が増感される量を用いるのであつて、その量
は有機光導電体の種類により異なるが概して、有
機光導電体に対して重量比で0.01％から100％、
好ましくは0.1％から30％の範囲である。
本発明に用いるピリリウム化合物は、例えば
２，６−ジ−tert−ブチル−４−メチルピリリウ
ム塩を、等モルの１−アニリノ−３−フエニルイ
ミノプロペンと反応させた後、さらに等モルの
２，６−ジフエニル−４−メチルピリリウム塩と
反応させることによつて得られる。この反応は第
一段階は無水酢酸中で第二段階は無水酢酸ナトリ
ウム等の塩基存在下に無水酢酸中で行うことが望
ましい。第一段階目の反応において無水酢酸の量
は２，６−ジ−tert−ブチル−４−メチルピリリ
ウム塩1gに対し１〜20ml、好ましくは２〜10ml
である。反応温度は80°から還流温度までで行わ
れるが100℃前後が好ましい。反応時間は１分か
ら１時間であるが、好ましくは10分から30分であ
る。第二段階目の反応を行うに先立つて中間体を
単離することも可能である。中間体の単離は第一
段階目の反応混合物をエーテル等の、中間体の貧
溶媒となる有機溶媒で希釈し、中間体を晶析させ
ればよい。第二段階目の反応において無水酢酸ナ
トリウムの量は２，６−ジフエニル−４−メチル
ピリリウム塩１モルに対して２〜３モル相当量用
いるのが好ましい。反応時間、反応温度は第一段
階の条件と同様である。
次に合成例により本発明に用いるピリリウム化
合物の代表的な合成方法を示す。なお、２，６−
ジ−tert−ブチル−４−メチルピリリウム塩、
２，６−ジフエニル−４−メチルピリリウム塩は
リービツヒ アナーレン デア ヘミエ
（Liebigs Annalen der Chemie）625、74（1959）
に記載されている方法によつて合成した。
合成例−１（化合物−(1)の合成）
２，６−ジ−tert−ブチル−４−メチルピリリ
ウムパークロレート（3.07ｇ、0.01mol）、１−ア
ニリノ−３−フエニルイミノプロペン（2.22ｇ、
0.01mol）をよく混合し、無水酢酸５mlを加え
た。混合物を100℃に過熱した後10分間攪拌し、
ついで２，６−ジフエニル−４−メチルピリリウ
ムパークロレート（3.47ｇ、0.01mol）、無水酢酸
ナトリウム（1.97ｇ、0.024mmol）を加え、さら
に30分間攪拌を続けた。室温まで冷却した反応混
合物にエーテル50mlを加え氷冷下攪拌を続けた。
析出する結晶を濾取水洗乾燥した後メタノールよ
り再結晶し化合物−(1)を融点（分解点）182−186
℃の赤紫色の結晶として得た。（収量2.49ｇ、収
率43％）
元素分析 分子式 C35H37cl1O6
Ｃ Ｈ cl
計算値（％） 71.36 6.33 6.02
実験値（％） 71.13 6.32 6.12
合成例−２（化合物−(3)の合成）
四塩化錫（104.2ｇ、0.40mol）、塩化ピバロイ
ル（96.6ｇ、0.80mol）の混合物中へ水冷下攪拌
しながら２−メチル−２−プロペン（30.8ｇ、
0.44mol）を滴下反応させた。滴下終了後１時間
攪拌を続けた後、60％過塩素酸60ｇを含む氷水
500ｇ中へ反応混合物を激しく攪拌しながら注ぎ、
さらに１時間攪拌を続けた。析出する固体を集
め、酢酸エチル120mlで再結晶し２，６−ジ−
tert−ブチル−４−エチルピリリウムパークロレ
ートを融点160−164℃の白色針状結晶として得
た。（収量29.58ｇ、収率23.1％）
元素分析 分子式 C15H25O5cl1
Ｃ Ｈ cl
計算値（％） 56.16 7.85 11.05
実験値（％） 55.90 7.86 11.02
次に上記ピリリウム塩と２，６−ジフエニル−
４−メチルピリリウムパークロレートを用い合成
例−１と同様の操作を行うことにより化合物−(3)
を融点238−239℃の緑がかつた金色の結晶として
得た。
元素分析 分子式 C36H39O6cl1
Ｃ Ｈ cl
計算値（％） 71.69 6.52 5.88
実験値（％） 71.43 6.53 5.90
合成例−３（化合物−(8)の合成）
−20℃へ冷却した２，６−ジフエニル−γ−ピ
ロン（1.24ｇ、5mmol）の無水THF（10ml）溶液
にｎ−ブチルリチウム（1.7Mヘキサン溶液3.5
ml、6mmol）を滴下反応させた。一時間後反応
混合物を６％過塩素酸水溶液50ml中へ注ぎ、析出
する固体を濾取し、少量の塩化メチレンに溶解し
た後にエーテル中へ再沈澱させ、析出する黄色固
体を濾取乾燥させた。（２，６−ジフエニル−３
−ｎ−プロピルピリリウムパークロレート、収量
0.88ｇ、収率45％）
次に上記ピリリウム塩の粗結晶と２，６−ジ−
tert−ブチル−４−メチル−ピリリウムパークロ
レートを用い合成例−１と同様の操作を行うこと
により化合物−(8)を融点233〜235℃の赤色がかつ
た金色の結晶として得た。
元素分析 分子式 C38H43O6cl1
Ｃ Ｈ cl
計算値（％） 72.31 6.87 5.62
実験値（％） 72.21 6.85 5.59
本発明の改良された電子写真感光材料は、少な
くとも支持体、感光層からなる。
本発明において使用する支持体は導電化処理を
必要とする。具体的な導電化処理としては、アル
ミニウム、金、パラジユーム、インジユーム等の
金属を蒸着する方法、又はIn2O3，SnO2等の金属
酸化物を蒸着する方法、又は金属粉やSnO2等の
金属酸化物等をバインダーポリマーに分散して塗
布する方法、又は有機四級塩化合物等をバインダ
ーポリマーとともに溶解、塗布する方法、ヨウ化
銅のアセトニトリル溶解を塗布する方法等をあげ
ることができる。
本発明の電子写真感光材料に用いられる有機光
導電性物質としては、従来から知られている数多
くのものを用いることができる。
例えば高分子のものでは次のようなものを挙げ
ることができる。
(1) 米国特許第3037861号明細書、特公昭34−
10966号公報、同42−19751号公報、同42−
25230号後方記載のポリビニルカルバゾールお
よびその誘導体、
(2) 特公昭43−18674号後方、特公昭43−19192号
公報記載のポリビニルピレン、ポリビニルアン
トラセン、ポリ−２−ビニル−４−（4′−ジメ
チルアミノフエニル）−５−フエニル−オキサ
ゾール、ポリ−３−ビニル−Ｎ−エチルカルバ
ゾールなどのビニル重合体、
(3) 特公昭43−19193号公報記載のポリアセナフ
チレン、ポリイソデン、アセナフチレンとスチ
レンの共重合などのような重合体、
(4) 特公昭56−13940号公報などに記載のピレン
−ホルムアルデヒド樹脂、ブロムピレン−ホル
ムアルデヒド樹脂、エチルカルバゾール−ホル
ムアルデヒド樹脂などの縮合樹脂、
(5) 特開昭56−90883号及び特開昭56−161550号
公報に記載された各種のトリフエニルメタンポ
リマー。
また低分子のものでは次のようなものを挙げ
ることができる。
(6) 米国特許第3112197号明細書などに記載され
ているトリアゾール誘導体、
(7) 米国特許第3189447号明細書などに記載され
ているオキサジアゾール誘導体、
(8) 特公昭37−16096号公報などに記載されてい
るイミダゾール誘導体、
(9) 米国特許第3615402号、同第3820989号、同
3542544号、特公昭45−555号、特公昭51−
10983号、特開昭51−93224号、特開昭55−
17105号。特開昭56−4148号、特開昭55−
108667号、特開昭55−156953号、特開昭56−
36656号明細書、公報などに記載のポリアリー
ルアルカン誘導体、
(10) 米国特許第3180729号、米国特許第4278746
号、特開昭55−88064号、特開昭55−88065号、
特開昭49−105537号、特開昭55−51085号、特
開昭56−80051号、特開昭56−88141号、特開昭
57−45545号、特開昭54−112637号、特開昭55
−74546号明細書、公報などに記載されている
ピラゾリン誘導体およびピラゾロン誘導体、
(11) 米国特許第3615404号明細書、特公昭51−
10105号、特開昭54−83435号、特開昭54−
110836号、特開昭54−119925号、特公昭46−
3712号、特公昭47−28336号明細書、公報など
に記載されているフエニレンジアミン誘導体、
(12) 米国特許3567450号、特公昭49−35702号、西
独国特許（DAS）1110518号、米国特許第
3180703号、米国特許第3240597号、米国特許第
3658520号、米国特許第4232103号、米国特許第
4175961号、米国特許第4012376号、特開昭55−
144250号、特開昭56−119132号、特公昭39−
27577号、特開昭56−22437号明細書、公報など
に記載されているアリールアミン誘導体、
(13) 米国特許3526501号明細書記載のアミノ置換
カルコン誘導体、
(14) 米国特許第3542546号明細書などに記載のＮ，
Ｎ−ビカルバジル誘導体、
(15) 米国特許第3257203号明細書などに記載のオ
キサゾール誘導体、
(16) 特開昭56−46234号公報などに記載のスチリ
ルアントラセン誘導体、
(17) 特開昭54−110837号公報などに記載されてい
るフルオレノン誘導体、
(18) 米国特許第3717462号、特開昭54−59143号
（米国特許第4150987号に対応）、特開昭55−
52063号、特開昭55−52064号、特開昭55−
46760号、特開昭55−85495号、特開昭57−
11350号、特開昭57−148749号、特開昭57−
64244号明細書などに開示されているヒドラゾ
ン誘導体、
(19) 特公昭39−11546号、特開昭55−79450号（米
国特許4265990号に対応）、米国特許4047949号
明細書などに開示されているベンジジン誘導体
などがある。
これらの有機光導電性物質は、感光層中に20〜
99重量％の範囲で用いることが好ましい。
有機光導電体が低分子化合物の場合には、適当
な被膜性を有する高分子化合物を結着剤として用
いることができる。具体的には、ポリアミド、ポ
リウレタン、ポリエステル、エポキシ樹脂、ポリ
ケトン、スチレン系重合体および共重合体、ポリ
−Ｎ−ビニルカルバゾール、ポリカーボネート、
ポリエステルカーボネート、ポリスルホン、塩化
ビニール樹脂、塩化ビニリデン樹脂、酢酸ビニル
樹脂、アクリル樹脂等の各種の高分子化合物を挙
げることができる。有機光導電体が高分子化合物
の場合には、それ自体被膜性を有するが、必要に
応じて上記の高分子化合物を添加しても良い。
結着剤の添加量は有機光導電体の種類により異
なるが低分子有機光導電体の場合有機光導電体に
対して重量比で50〜200％使用するのが望ましい。
有機光導電体が高分子の場合は１％〜50％使用す
るのが望ましい。
本発明の記録材料には化学増感剤を用いること
ができるが化学増感剤としては、例えばトリニト
ロフルオレノン、クロラニル、テトラシアノエチ
レン等の電子吸引性化合物、特開昭58−65439号、
特開昭58−102239号等に記載の化合物等をあげる
ことができる。
本発明の電子写真感光材料中には、必要に応じ
て公知の補剤（structure agent）、可塑剤、染
料、顔料等を、本発明の電子写真感光材料の特性
を損わない範囲で含有させることができる。
補強剤としてシアノエチルセルロース、ニトリ
ルゴム、ビスフエノールＡのポリカルボネート、
線状ポリエステルスチレン−ブタジエン共重合
体、塩化ビニリデン−アクリロニトリル共重合体
などを用いることができる。可塑剤として塩素化
ビフエニル、エポキシ樹脂、トリフエニルメタン
化合物、クマロン樹脂、低分子量キシレン樹脂な
どを用いることができる。
本発明の電子写真感光材料には、その他に特公
昭49−46263号公報に記載されているがごとくの
可塑剤、特公昭57−19423号公報に記載のシラン
カツプリング剤、硬化触媒及び／又は架橋剤、特
開昭51−88025号公報記載のフツ素含有界面活性
剤、特公昭57−19424号公報記載のルイス酸、お
よび特公昭57−19782号公報記載の電子供与性物
質を含有することができる。
本発明の電子写真感光材料の作成に際しては溶
媒として、ベンゼン、トルエン、キシレン、クロ
ロベンゼン、ジクロロメタン、ジクロロエタン、
トリクロロエタン、シクロヘキサノン、テトラヒ
ドロフラン、ジオキサン等およびこれらの混合溶
剤のうちから高分子有機光導電体、増感色素およ
び必要に応じて添加される成分を共に溶解または
分散する溶媒を用いることができる。
本発明により感光材料は、次の様にして得るこ
とが出来る。
感光材料とするには、光導電性物質、本発明の
ピリリウム系化合物および必要に応じて添加され
る成分を所望の割合で溶剤に溶解あるいは分散せ
しめて、導電性支持体上に塗布、乾燥するか、上
記成分を導電性支持体上に溶融塗布、あるいは感
光性薄膜を溶液から、または溶融押し出し法等で
作成し、自己支持性フイルムとすることができ
る。また塗布にあたつては塗布溶液中に公知の塗
布界面活性剤を含有させることができる。
本発明の電子写真感光材料は表面保護層を有す
ることができる。
表面保護層としては微粒子を含有する決着樹脂
の層が例示できる。用いられる結着樹脂として
は、ポリエステルカーボネート、ポリスルホン、
ポリエーテル、ポリエステル、ポリカーボネー
ト、ポリアミド、ポリイミド、ポリウレタン、ア
クリル酸エステル重合体および共重合体、メタク
リル酸エステル重合体及び共重合体、スチレン系
樹脂、ポリビニルアセタール、ポリビニルカルバ
ゾール、塩化ビニル系樹脂、塩化ビニリデン系樹
脂、塩素化ポリオレフイン、酢酸ビニル系樹脂、
アルキルド樹脂、キシレン樹脂、ケント樹脂、セ
ルロース類があるが、これに限定されるものでは
ない。これら樹脂は、単独又は２種以上併用して
使用することができる。
微粒子としては各種の微粒子を用いることがで
きる。例えばシリカ、炭酸カルシユーム、マイ
カ、クレー、ボロンナイトライド等の無機絶縁性
微粒子、酸化チタン、酸化アルミニウム、酸化マ
グネシユーム、酸化亜鉛、二酸化スズ、酸化ビス
マス等の金属酸化物、ステアリン酸亜鉛、ステア
リン酸カルシユーム、ラウリン酸亜鉛等の長鎖有
機酸金属塩、ポリプロピレン、ポリエチレン、ポ
リアミド、ポリフツ化ビニリデン、ポリテトラフ
ルオロエチレン等の有機微粒子等をあげることが
できるが、これに限定されるものでない。これら
の微粒子のうち、特に容易に分散できるシリカ、
酸化アルミニウム、酸化チタンを好ましく用いる
ことができる。
本発明の電子写真感光材料は必要に応じて、支
持体と感光層との間、あるいは感光層と表面保護
層の間に、各種目的（たとえば接着の改良等）の
ために、中間層を設けても良い。
本発明の電子写真感光材料は、その背面にすべ
り性、帯電性、耐ブロツキング性、アンチハレー
シヨン性等の諸特性を改良するための層を設けて
もよい。
「実施例」
以下に本発明の実施例を示すが、本発明は、こ
れに限定されるものではない。
実施例 １
"Industrial Application Field" The present invention relates to a highly sensitive electrophotographic material mainly composed of an organic photoconductive substance, and particularly to an electrophotographic material exhibiting high sensitivity in the wavelength region of a semiconductor laser. "Prior Art" In recent years, electrophotographic systems using semiconductor lasers as light sources have been actively developed. semiconductor laser is
Compared to gas lasers such as He-Ne, they are smaller and cheaper, and have major advantages such as being able to be directly modulated, but their oscillation wavelengths are often over 750 nm. Therefore, the photoreceptor used in this system must have absorption at 750 nm or higher and exhibit high sensitivity, and various sensitizing dyes are being developed. However, organic compounds that absorb in such long wavelength ranges are generally unstable with respect to heat exchangers and humidity, causing problems in manufacturing and handling.
Furthermore, photosensitive materials produced using these materials deteriorate significantly over time, and many of them lose their function as photoreceptors when stored for a long period of time. In addition, even if the main absorption is in this wavelength range, there are some that have small extinction coefficients or only show low electrophotographic sensitivity, so the current situation is not necessarily satisfactory, and it is necessary to achieve even higher sensitivity and higher durability. It is desired to develop an electrophotographic photoreceptor as shown in FIG. "Problems to be Solved by the Invention" A first object of the present invention is to provide an electrophotographic material containing an organic photoconductive substance and a pyrylium compound and having high sensitivity. A second object of the present invention is to provide an electrophotographic photosensitive material that is durable against heat and humidity. A third object of the present invention is to provide an electrophotographic material that has main absorption in the oscillation wavelength region of a semiconductor laser and exhibits high sensitivity. "Means for Solving the Problems" That is, as a result of intensive research, the present inventors solved the above problems by producing an electrophotographic light-sensitive material containing at least one compound represented by the following general formula (). I was able to do that. General formula () In the formula, R 1 , R 2 , R 4 , and R 5 represent a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, and R 3 represents a hydrogen atom, a halogen atom, or a substituted or unsubstituted aryl group. Indicates an alkyl group or a substituted or unsubstituted aryl group. R1 , R2 , R3 ,
The hydrogen atoms and aryl groups of R 4 and R 5 may be the same or different. X represents an anion. In addition, preferable alkyl groups for R 1 , R 2 , R 3 , R 4 , and R 5 are alkyl groups having 1 to 18 carbon atoms, and specifically, methyl, ethyl, n-propyl,
iso-propyl, n-butyl, sec-butyl, tert
-butyl, n-amyl, n-hexyl, n-heptyl, n-nonyl, n-dodecyl, 2-ethylhexyl, fluoromethyl, chloromethyl, bromomethyl, trifluoromethyl, methoxymethyl,
Examples include cyanomethyl and alkylthiomethyl. Further, preferred aryl groups have 6 to 24 carbon atoms.
aryl groups, and specific examples include phenyl, tolyl, chlorophenyl, fluorophenyl, naphthyl, and the like. Specific examples of the anion of X include perchlorate, tetrafluoroborate, iodide,
Examples include chloride, bromide, sulfate, periodide, p-toluenesulfonate, and the like. In the compound used in the present invention, the tert-butyl group (hereinafter referred to as tert-Bu group) introduced into one pyrylium ring plays a role in improving the stability and solubility of the compound. . The phenyl group (hereinafter referred to as φ- group) introduced into the other pyrylium ring exhibits main absorption.
This is for setting around 780nm. R1 ～
R5 has the role of finely adjusting the absorption maximum wavelength as desired. Next, typical examples of the compound represented by the general formula () used in the present invention are shown below, but the present invention is not limited thereto. The amount of pyriliu-based compound used in the present invention is used to sensitize the organic photoconductor, and the amount varies depending on the type of organic photoconductor, but in general, the weight ratio to the organic photoconductor is 0.01. % to 100%,
Preferably it is in the range of 0.1% to 30%. The pyrylium compound used in the present invention can be prepared by, for example, reacting 2,6-di-tert-butyl-4-methylpyrylium salt with an equimolar amount of 1-anilino-3-phenyliminopropene, and then reacting an equimolar amount of 1-anilino-3-phenyliminopropene. Obtained by reaction with 2,6-diphenyl-4-methylpyrylium salt. This reaction is preferably carried out in acetic anhydride in the first step and in acetic anhydride in the second step in the presence of a base such as anhydrous sodium acetate. In the first step reaction, the amount of acetic anhydride is 1 to 20 ml, preferably 2 to 10 ml, per 1 g of 2,6-di-tert-butyl-4-methylpyrylium salt.
It is. The reaction temperature is from 80° to reflux temperature, preferably around 100°C. The reaction time is 1 minute to 1 hour, preferably 10 minutes to 30 minutes. It is also possible to isolate the intermediate prior to carrying out the second step reaction. The intermediate can be isolated by diluting the first-stage reaction mixture with an organic solvent such as ether that is a poor solvent for the intermediate, and crystallizing the intermediate. In the second stage reaction, it is preferable to use anhydrous sodium acetate in an amount equivalent to 2 to 3 moles per mole of 2,6-diphenyl-4-methylpyrylium salt. The reaction time and reaction temperature are the same as those in the first stage. Next, a typical method for synthesizing the pyrylium compound used in the present invention will be shown using a synthesis example. In addition, 2,6-
di-tert-butyl-4-methylpyrylium salt,
The 2,6-diphenyl-4-methylpyrylium salt was prepared by Liebigs Annalen der Chemie 625, 74 (1959).
It was synthesized by the method described in . Synthesis Example-1 (Synthesis of compound-(1)) 2,6-di-tert-butyl-4-methylpyrylium perchlorate (3.07 g, 0.01 mol), 1-anilino-3-phenyliminopropene (2.22 g,
0.01 mol) were mixed well, and 5 ml of acetic anhydride was added. The mixture was heated to 100 °C and then stirred for 10 min.
Then, 2,6-diphenyl-4-methylpyrylium perchlorate (3.47 g, 0.01 mol) and anhydrous sodium acetate (1.97 g, 0.024 mmol) were added, and stirring was continued for an additional 30 minutes. 50 ml of ether was added to the reaction mixture cooled to room temperature, and stirring was continued under ice cooling.
The precipitated crystals were collected by filtration, washed with water, dried, and then recrystallized from methanol to obtain compound-(1) with a melting point (decomposition point) of 182-186.
Obtained as red-purple crystals at °C. (Yield 2.49g, yield 43%) Elemental analysis Molecular formula C 35 H 37 cl 1 O 6 C H cl Calculated value (%) 71.36 6.33 6.02 Experimental value (%) 71.13 6.32 6.12 Synthesis example-2 (compound-(3) Synthesis) 2-Methyl-2-propene (30.8 g,
0.44 mol) was added dropwise to react. After stirring for 1 hour after dropping, add ice water containing 60g of 60% perchloric acid.
Pour the reaction mixture into 500 g with vigorous stirring,
Stirring was continued for an additional hour. The precipitated solid was collected and recrystallized with 120 ml of ethyl acetate to give 2,6-di-
Tert-butyl-4-ethylpyrylium perchlorate was obtained as white needle-like crystals with a melting point of 160-164°C. (Yield 29.58g, yield 23.1%) Elemental analysis Molecular formula C 15 H 25 O 5 cl 1 C H cl Calculated value (%) 56.16 7.85 11.05 Experimental value (%) 55.90 7.86 11.02 Next, the above pyrylium salt and 2,6- Diphenyl
By performing the same operation as in Synthesis Example-1 using 4-methylpyrylium perchlorate, compound-(3)
was obtained as greenish-gold crystals with a melting point of 238-239°C. Elemental analysis Molecular formula C 36 H 39 O 6 cl 1 C H cl Calculated value (%) 71.69 6.52 5.88 Experimental value (%) 71.43 6.53 5.90 Synthesis example-3 (Synthesis of compound-(8)) 2 cooled to -20℃ , 6-diphenyl-γ-pyrone (1.24 g, 5 mmol) in anhydrous THF (10 ml) was mixed with n-butyllithium (1.7 M hexane solution 3.5
ml, 6 mmol) was dropped and reacted. After one hour, the reaction mixture was poured into 50 ml of a 6% aqueous perchloric acid solution, the precipitated solid was collected by filtration, dissolved in a small amount of methylene chloride, and reprecipitated in ether, and the precipitated yellow solid was collected by filtration and dried. . (2,6-diphenyl-3
-n-propylpyrylium perchlorate, yield
0.88g, yield 45%) Next, the crude crystals of the above pyrylium salt and 2,6-di-
The same procedure as in Synthesis Example 1 was carried out using tert-butyl-4-methyl-pyrylium perchlorate to obtain compound (8) as red-gold crystals with a melting point of 233-235°C. Elemental analysis Molecular formula C 38 H 43 O 6 cl 1 C H cl Calculated value (%) 72.31 6.87 5.62 Experimental value (%) 72.21 6.85 5.59 The improved electrophotographic light-sensitive material of the present invention comprises at least a support and a photosensitive layer. . The support used in the present invention requires conductive treatment. Specific conductive treatments include methods of vapor-depositing metals such as aluminum, gold, palladium, and indium, methods of vapor-depositing metal oxides such as In 2 O 3 and SnO 2 , or methods of vapor-depositing metal powders, SnO 2 , etc. Examples include a method in which a metal oxide or the like is dispersed in a binder polymer and applied, a method in which an organic quaternary salt compound or the like is dissolved and applied together with a binder polymer, and a method in which copper iodide is dissolved in acetonitrile and applied. As the organic photoconductive substance used in the electrophotographic photosensitive material of the present invention, many conventionally known organic photoconductive substances can be used. Examples of polymers include the following: (1) U.S. Patent No. 3037861, Japanese Patent Publication No. 34-
Publication No. 10966, Publication No. 42-19751, Publication No. 42-
Polyvinylcarbazole and its derivatives described in the rear of No. 25230, (2) Polyvinylpyrene, polyvinylanthracene, poly-2-vinyl-4-(4'-dimethyl) vinyl polymers such as (aminophenyl)-5-phenyl-oxazole, poly-3-vinyl-N-ethylcarbazole, (3) polyacenaphthylene, polyisodene, acenaphthylene and styrene described in Japanese Patent Publication No. 19193-1973; (4) Condensation resins such as pyrene-formaldehyde resin, brompyrene-formaldehyde resin, and ethylcarbazole-formaldehyde resin described in Japanese Patent Publication No. 56-13940, (5) JP-A-56 -90883 and various triphenylmethane polymers described in JP-A-56-161550. In addition, the following can be mentioned as low molecular weight compounds. (6) Triazole derivatives described in U.S. Patent No. 3112197 etc., (7) Oxadiazole derivatives described in U.S. Patent No. 3189447 etc., (8) Japanese Patent Publication No. 37-16096 (9) U.S. Patent No. 3615402, U.S. Patent No. 3820989, U.S. Pat.
No. 3542544, Special Publication No. 1977-555, Special Publication No. 1971-
No. 10983, JP-A-51-93224, JP-A-55-
No. 17105. JP-A-56-4148, JP-A-55-
No. 108667, JP-A-55-156953, JP-A-56-
Polyarylalkane derivatives described in 36656 specification, publications, etc., (10) U.S. Patent No. 3180729, U.S. Patent No. 4278746
No., JP-A-55-88064, JP-A-55-88065,
JP-A-49-105537, JP-A-55-51085, JP-A-56-80051, JP-A-56-88141, JP-A-Sho
No. 57-45545, JP-A No. 112637-1983, JP-A-55
Pyrazoline derivatives and pyrazolone derivatives described in -74546 specification, publications, etc. (11) U.S. Patent No. 3615404 specification, Japanese Patent Publication No. 1983-
No. 10105, JP-A No. 1983-83435, JP-A No. 1983-
No. 110836, Japanese Patent Application Publication No. 119925, Publication No. 119925, Publication No. 119925, Publication No. 119925-
Phenylenediamine derivatives described in No. 3712, Japanese Patent Publication No. 47-28336, publications, etc., (12) U.S. Patent No. 3567450, Japanese Patent Publication No. 49-35702, West German Patent (DAS) No. 1110518, U.S. Patent No.
3180703, U.S. Patent No. 3240597, U.S. Patent No.
3658520, U.S. Patent No. 4232103, U.S. Patent No.
No. 4175961, U.S. Patent No. 4012376, Japanese Unexamined Patent Publication No. 1987-
No. 144250, JP-A-56-119132, JP-A No. 119132-
Arylamine derivatives described in No. 27577, JP-A No. 56-22437, publications, etc. (13) Amino-substituted chalcone derivatives described in U.S. Pat. No. 3,526,501, (14) U.S. Pat. No. 3,542,546 N listed in etc.
N-bicalbasil derivatives, (15) Oxazole derivatives described in US Pat. No. 3,257,203, etc., (16) Styryl anthracene derivatives described in JP-A-56-46234, etc., (17) JP-A-54-110837. Fluorenone derivatives described in publications such as (18) U.S. Patent No. 3717462, JP-A-54-59143 (corresponding to U.S. Patent No. 4,150-987), JP-A-55-
No. 52063, JP-A-55-52064, JP-A-55-
No. 46760, JP-A-55-85495, JP-A-57-
No. 11350, JP-A-57-148749, JP-A-57-
64244, (19) hydrazone derivatives disclosed in Japanese Patent Publication No. 39-11546, JP-A-55-79450 (corresponding to U.S. Pat. No. 4,265,990), U.S. Pat. No. 4,047,949, etc. There are benzidine derivatives. These organic photoconductive substances are present in the photosensitive layer from 20 to
It is preferably used in a range of 99% by weight. When the organic photoconductor is a low-molecular compound, a high-molecular compound having suitable film properties can be used as a binder. Specifically, polyamide, polyurethane, polyester, epoxy resin, polyketone, styrenic polymer and copolymer, poly-N-vinylcarbazole, polycarbonate,
Examples include various polymer compounds such as polyester carbonate, polysulfone, vinyl chloride resin, vinylidene chloride resin, vinyl acetate resin, and acrylic resin. When the organic photoconductor is a polymer compound, it itself has film properties, but the above-mentioned polymer compound may be added as necessary. The amount of the binder added varies depending on the type of organic photoconductor, but in the case of a low-molecular organic photoconductor, it is preferably used in an amount of 50 to 200% by weight based on the organic photoconductor.
When the organic photoconductor is a polymer, it is preferably used in an amount of 1% to 50%. Chemical sensitizers can be used in the recording material of the present invention, and examples of chemical sensitizers include electron-withdrawing compounds such as trinitrofluorenone, chloranil, and tetracyanoethylene;
Examples include compounds described in JP-A-58-102239 and the like. The electrophotographic light-sensitive material of the present invention may contain known structure agents, plasticizers, dyes, pigments, etc., as necessary, within a range that does not impair the properties of the electrophotographic light-sensitive material of the present invention. be able to. Cyanoethyl cellulose, nitrile rubber, bisphenol A polycarbonate as reinforcing agents,
Linear polyester styrene-butadiene copolymer, vinylidene chloride-acrylonitrile copolymer, etc. can be used. As the plasticizer, chlorinated biphenyl, epoxy resin, triphenylmethane compound, coumaron resin, low molecular weight xylene resin, etc. can be used. In addition, the electrophotographic material of the present invention may include a plasticizer as described in Japanese Patent Publication No. 49-46263, a silane coupling agent as described in Japanese Patent Publication No. 57-19423, a curing catalyst, and/or Contains a crosslinking agent, a fluorine-containing surfactant described in JP-A No. 51-88025, a Lewis acid described in JP-A-57-19424, and an electron-donating substance described in JP-A-57-19782. I can do it. When producing the electrophotographic material of the present invention, benzene, toluene, xylene, chlorobenzene, dichloromethane, dichloroethane,
Among trichloroethane, cyclohexanone, tetrahydrofuran, dioxane, etc., and mixed solvents thereof, a solvent capable of dissolving or dispersing the polymeric organic photoconductor, the sensitizing dye, and optionally added components can be used. A photosensitive material according to the present invention can be obtained as follows. To prepare a photosensitive material, a photoconductive substance, the pyrylium compound of the present invention, and optionally added components are dissolved or dispersed in a solvent in a desired ratio, coated on a conductive support, and dried. Alternatively, a self-supporting film can be obtained by melt-coating the above-mentioned components onto a conductive support, or by preparing a photosensitive thin film from a solution or by a melt-extrusion method. Further, during coating, a known coating surfactant can be included in the coating solution. The electrophotographic material of the present invention may have a surface protective layer. An example of the surface protective layer is a layer of binding resin containing fine particles. Binder resins used include polyester carbonate, polysulfone,
Polyether, polyester, polycarbonate, polyamide, polyimide, polyurethane, acrylic ester polymer and copolymer, methacrylic ester polymer and copolymer, styrene resin, polyvinyl acetal, polyvinyl carbazole, vinyl chloride resin, vinylidene chloride based resin, chlorinated polyolefin, vinyl acetate resin,
Examples include, but are not limited to, alkylated resins, xylene resins, Kent resins, and celluloses. These resins can be used alone or in combination of two or more. Various types of fine particles can be used as the fine particles. For example, inorganic insulating fine particles such as silica, calcium carbonate, mica, clay, and boron nitride, metal oxides such as titanium oxide, aluminum oxide, magnesium oxide, zinc oxide, tin dioxide, and bismuth oxide, zinc stearate, and calcium stearate. Examples include, but are not limited to, long-chain organic acid metal salts such as zinc laurate, organic fine particles such as polypropylene, polyethylene, polyamide, polyvinylidene fluoride, and polytetrafluoroethylene. Among these fine particles, silica, which can be particularly easily dispersed,
Aluminum oxide and titanium oxide can be preferably used. In the electrophotographic material of the present invention, an intermediate layer may be provided between the support and the photosensitive layer or between the photosensitive layer and the surface protective layer for various purposes (for example, to improve adhesion, etc.), if necessary. It's okay. The electrophotographic material of the present invention may be provided with a layer on its back surface for improving various properties such as slip properties, charging properties, blocking resistance, and antihalation properties. "Example" Examples of the present invention are shown below, but the present invention is not limited thereto. Example 1
【表】
上記組成の感光液を調製し、ついでワイヤーバ
ーを用いて酸化インジウムの蒸着膜を有する厚さ
100μmのポリエチレンテレフタレートフイルム上
に塗布、乾燥した。厚さ8.4μmの光導電層を有す
る電子写真フイルムが得られた。このフイルムは
第１図に示すように半導体レーザーの発振領域内
（785nm）に吸収極大を有する。
次に得られた電子写真フイルムを複写紙試験装
置SP−428（川口電機(株)製）を用いて、スタチツ
ク方式により＋7.5KVでコロナ帯電し、785nmの
単色光で露光し電子写真特性を調べた。
特性の電荷保持力は、コロナ帯電した後暗所で
60秒後に電位を測定し、初期電位の残存率（％）
を求めた。
また感度として、露光前の電位が光減衰して1/
２になる露光量（E50）と1/10になる露光量（E90）
を求めた。
電荷保持力は90％と良好な値を示し、感度は電
界強度0.81×106ｖ／cmにおいて99erg／cm2（E50）
〜641erg／cm2（E90）と極めて高感度なものであ
つた。
また光源としてタングステン光（4lux）をもち
いた場合も電荷保持力90％、E5026lux−sec、E90
187lox−sec（電界強度0.84×106ｖ／cm）と良好
な値を示した。
次に上記電子写真フイルムを50℃、80％RHの
条件下に10週間放置した後、吸収極大、電子写真
特性を調べたところ、ほとんど変化が認められな
かつた。
実施例 ２
本発明の化合物−(1)，(3)，(8)を用い実施例−１
と同様の操作を行つてそれぞれ電子写真フイルム
を得た。各フイルムの吸収極大、電子写真特性に
ついての結果を第１表に示す。[Table] A photosensitive solution having the above composition was prepared, and then a wire bar was used to form a vapor-deposited film of indium oxide.
It was coated on a 100 μm polyethylene terephthalate film and dried. An electrophotographic film having a photoconductive layer with a thickness of 8.4 μm was obtained. As shown in FIG. 1, this film has an absorption maximum within the oscillation region of the semiconductor laser (785 nm). Next, the obtained electrophotographic film was statically charged with a corona at +7.5 KV using a copying paper tester SP-428 (manufactured by Kawaguchi Electric Co., Ltd.), and exposed to monochromatic light of 785 nm to determine its electrophotographic properties. Examined. The characteristic charge retention ability is that in the dark after corona charging.
Measure the potential after 60 seconds and calculate the residual rate (%) of the initial potential
I asked for In addition, as for sensitivity, the potential before exposure is photo-attenuated and 1/
The exposure amount that becomes 2 (E 50 ) and the exposure amount that becomes 1/10 (E 90 )
I asked for Charge retention shows a good value of 90%, and sensitivity is 99erg/cm 2 (E 50 ) at an electric field strength of 0.81×10 6 v/cm.
It had an extremely high sensitivity of ~641 erg/cm 2 (E 90 ). Also, when using tungsten light (4lux) as a light source, the charge retention power is 90%, E 50 26lux-sec, E 90
It showed a good value of 187 lox-sec (electric field strength 0.84×10 6 v/cm). Next, the electrophotographic film was left under conditions of 50° C. and 80% RH for 10 weeks, and its absorption maximum and electrophotographic properties were examined, and almost no changes were observed. Example 2 Example-1 using the compounds-(1), (3), and (8) of the present invention
Electrophotographic films were obtained in the same manner as above. Table 1 shows the results regarding absorption maximum and electrophotographic properties of each film.
【表】
第１表より明らかなようにこれらのフイルムは
いずれも半導体レーザーの発振領域内に吸収極大
を持ち、良好な電子写真感度を有している。つぎ
にこれらのフイルムを50℃、80％RHの条件下に
10週間放置した後に上記諸特性を測定したところ
表−１とほとんど変化がなかつた。[Table] As is clear from Table 1, all of these films have an absorption maximum within the oscillation region of the semiconductor laser and have good electrophotographic sensitivity. Next, these films were placed at 50℃ and 80%RH.
When the above characteristics were measured after being left for 10 weeks, there was almost no change from Table 1.
第１図は実施例−１の電子写真フイルムの可視
へ近赤外領域の吸収スペクトルを示す。
FIG. 1 shows the absorption spectrum of the electrophotographic film of Example 1 in the visible to near infrared region.
Claims (1)
される化合物の少くとも一種以上とを含有するこ
とを特徴とする電子写真感光材料。 一般式（） 式中、R1，R2，R4，R5は水素原子、置換もし
くは未置換のアルキル基、置換もしくは未置換の
アリール基を示し、R3は水素原子、ハロゲン原
子、置換もしくは未置換のアルキル基、置換もし
くは未置換のアリール基を示す。R1，R2，R3，
R4，R5の水素原子、アルキル基、アリール基は
それぞれ同じものでも異つていてもよい。Ｘはア
ニオンを示す。[Scope of Claims] 1. An electrophotographic light-sensitive material comprising an organic photoconductive substance and at least one compound represented by the following general formula (). General formula () In the formula, R 1 , R 2 , R 4 , and R 5 represent a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, and R 3 represents a hydrogen atom, a halogen atom, or a substituted or unsubstituted aryl group. Indicates an alkyl group or a substituted or unsubstituted aryl group. R 1 , R 2 , R 3 ,
The hydrogen atom, alkyl group, and aryl group of R 4 and R 5 may be the same or different. X represents an anion.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20033285A JPS6259963A (en) | 1985-09-10 | 1985-09-10 | Electrophotographic sensitive material |
| DE3630389A DE3630389C2 (en) | 1985-09-05 | 1986-09-05 | Electrophotographic light-sensitive material |
| US06/903,918 US4663260A (en) | 1985-09-05 | 1986-09-05 | Electrophotographic light-sensitive material comprising organic photoconductor and pyrylium sensitizer |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20033285A JPS6259963A (en) | 1985-09-10 | 1985-09-10 | Electrophotographic sensitive material |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6259963A JPS6259963A (en) | 1987-03-16 |
| JPH0513514B2 true JPH0513514B2 (en) | 1993-02-22 |
Family
ID=16422533
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP20033285A Granted JPS6259963A (en) | 1985-09-05 | 1985-09-10 | Electrophotographic sensitive material |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6259963A (en) |
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