JPH0516020B2 - - Google Patents
Info
- Publication number
- JPH0516020B2 JPH0516020B2 JP5288087A JP5288087A JPH0516020B2 JP H0516020 B2 JPH0516020 B2 JP H0516020B2 JP 5288087 A JP5288087 A JP 5288087A JP 5288087 A JP5288087 A JP 5288087A JP H0516020 B2 JPH0516020 B2 JP H0516020B2
- Authority
- JP
- Japan
- Prior art keywords
- electrophotographic photoreceptor
- photosensitive layer
- group
- photoreceptor
- electrophotographic
- 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 - Lifetime
Links
- 108091008695 photoreceptors Proteins 0.000 claims description 49
- -1 indoline compound Chemical class 0.000 claims description 24
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 4
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 239000010410 layer Substances 0.000 description 34
- 239000002800 charge carrier Substances 0.000 description 19
- 239000000126 substance Substances 0.000 description 16
- 150000001875 compounds Chemical class 0.000 description 10
- 230000035945 sensitivity Effects 0.000 description 10
- 239000011230 binding agent Substances 0.000 description 9
- 239000000975 dye Substances 0.000 description 9
- 238000012546 transfer Methods 0.000 description 8
- 239000000463 material Substances 0.000 description 6
- 239000000049 pigment Substances 0.000 description 6
- 230000001235 sensitizing effect Effects 0.000 description 6
- 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000004014 plasticizer Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 150000002476 indolines Chemical class 0.000 description 3
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- WUPHOULIZUERAE-UHFFFAOYSA-N 3-(oxolan-2-yl)propanoic acid Chemical compound OC(=O)CCC1CCCO1 WUPHOULIZUERAE-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052980 cadmium sulfide Inorganic materials 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical compound C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229910052711 selenium Inorganic materials 0.000 description 2
- 239000011669 selenium Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- FHIDEWWHKSJPTK-UHFFFAOYSA-N (3,5-dinitrophenyl)-phenylmethanone Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC(C(=O)C=2C=CC=CC=2)=C1 FHIDEWWHKSJPTK-UHFFFAOYSA-N 0.000 description 1
- YCANAXVBJKNANM-UHFFFAOYSA-N 1-nitroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2[N+](=O)[O-] YCANAXVBJKNANM-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
- FPKCTSIVDAWGFA-UHFFFAOYSA-N 2-chloroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3C(=O)C2=C1 FPKCTSIVDAWGFA-UHFFFAOYSA-N 0.000 description 1
- FPYUJUBAXZAQNL-UHFFFAOYSA-N 2-chlorobenzaldehyde Chemical compound ClC1=CC=CC=C1C=O FPYUJUBAXZAQNL-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- BXRFQSNOROATLV-UHFFFAOYSA-N 4-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(C=O)C=C1 BXRFQSNOROATLV-UHFFFAOYSA-N 0.000 description 1
- 229910000967 As alloy Inorganic materials 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical group O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- 229910001215 Te alloy Inorganic materials 0.000 description 1
- QLNFINLXAKOTJB-UHFFFAOYSA-N [As].[Se] Chemical compound [As].[Se] QLNFINLXAKOTJB-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- CWRYPZZKDGJXCA-UHFFFAOYSA-N acenaphthene Chemical compound C1=CC(CC2)=C3C2=CC=CC3=C1 CWRYPZZKDGJXCA-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- 229960001506 brilliant green Drugs 0.000 description 1
- HXCILVUBKWANLN-UHFFFAOYSA-N brilliant green cation Chemical compound C1=CC(N(CC)CC)=CC=C1C(C=1C=CC=CC=1)=C1C=CC(=[N+](CC)CC)C=C1 HXCILVUBKWANLN-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- ZXJXZNDDNMQXFV-UHFFFAOYSA-M crystal violet Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1[C+](C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 ZXJXZNDDNMQXFV-UHFFFAOYSA-M 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Substances OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
- 239000011888 foil 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
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- CXKWCBBOMKCUKX-UHFFFAOYSA-M methylene blue Chemical compound [Cl-].C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 CXKWCBBOMKCUKX-UHFFFAOYSA-M 0.000 description 1
- 229960000907 methylthioninium chloride Drugs 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 238000006385 ozonation reaction Methods 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 239000013034 phenoxy resin Substances 0.000 description 1
- 229920006287 phenoxy resin Polymers 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920002382 photo conductive polymer Polymers 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 238000011160 research Methods 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
- 239000001016 thiazine dye Substances 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-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
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000011787 zinc oxide 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
- G03G5/0664—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
- G03G5/0622—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
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Photoreceptors In Electrophotography (AREA)
Description
［産業上の利用分野］
本発明は電子写真感光体に関し、詳しくは導電
性支持体上にインドリン化合物を含有する感光層
を持つ電子写真感光体に関する。
［従来の技術］
従来、電子写真感光体の感光層には無機系の光
導電性物質としてセレン、硫化カドミウム、酸化
亜鉛などが広く用いられている。近年、有機系の
光導電性物質も研究が進み、電子写真感光体とし
て実用化されているものもある。有機系の光導電
性物質は、無機系の光導電性物質に比し、軽量で
あり、成膜が容易で、感光体の製造が容易である
という利点を持つ。
有機系光導電性物質としてはポリビニルカルバ
ゾールをはじめ、光導電性ポリマーに関して多く
の研究がなされてきたが、これらポリマー単独で
は皮膜性、可撓性、接着性が不良で、これらの欠
点を改良するために可塑剤、バインダーなどが添
加されるが、これにより感度が低下したり、残留
電位が増大するなどの別の問題を生じ易く、実用
化は極めて困難であつた。
一方、有機系の低分子光導電性物質はバインダ
ーとして皮膜性、可撓性、接着性などの優れたポ
リマーを選択すれば、容易に機械的特性の優れた
感光体を得ることができるが、高感度の感光体を
作成するのに適した化合物を見出すことが困難で
あつた。
また、特開昭59−151157号公報に記載される低
分子のスチルベン化合物などは、初期には高感度
を示すが、複写機に取り付けて繰り返し画像を出
すとスチルベン化合物がオゾン化や光劣化のため
に分解し、画質が低下して、画像ボケの発生した
画像しか得られなくなる。
［発明が解決しようとする問題点］
本発明の目的は、前述の従来の感光体の有する
種々の欠点を解消し、電子写真感光体として要求
される条件として高感度、高耐久性、高改造度、
高画質の全ての条件を充分に満足する電子写真感
光体を提供することである。
［問題点を解決する手段、作用］
本発明は、導電性支持体上に下記一般式で表わ
されるインドリン化合物を含有する感光層を設け
たことを特徴とする電子写真感光体から構成され
る。
一般式
式中、Ａは水素原子、脂肪族炭化水素基、置換
基を有してもよい芳香族炭化水素基または芳香族
複素環基を示し、R1，R2，R3，R4，R5およびR6
はそれぞれ独立に水素原子、ハロゲン原子、ニト
ロ基、置換基を有してもよいアルキル基、アラル
キル基あるいはアリール基を示し、また、R5と
R6は環を形成してもよい。
以下、本発明を具体的に説明する。
本発明電子写真感光体は、感光層中に前記一般
式で表わされるインドリン化合物を含有する。
前記一般式において、Ａは水素原子、メチル、
エチル、直鎖ないしは分枝状のプロピル、ブチ
ル、ペンチルなどのアルキル基、ベンゼン、ナフ
タリン、アントラセン、ピレン、アセナフテン、
フルオレンなどから誘導される芳香族炭化水素
基、ピリジン、ピロール、ピラゾール、ジベンゾ
フラン、カルバゾールなどから誘導される芳香族
複素環基であり、これらの芳香族炭化水素基およ
び芳香族複素環基は置換基を有してもよく、置換
基としてはメチル、エチルなどのアルキル基、塩
素原子、臭素原子などのハロゲン原子、メトキ
シ、エトキシなどのアルコキシ基、フエノキシな
どのアリールオキシ基、ジメチルアミノ、ジエチ
ルアミノなどのアルキルアミノ基、メチルチオ、
エチルチオなどのアルキルチオ基などが挙げられ
る。
R1，R2，R3，R4，R5およびR6は水素原子、塩
素原子、臭素原子などのハロゲン原子、ニトロ
基、メチル、エチル、直鎖ないしは分枝状のプロ
ピル、ブチル、ペンチルなどのアルキル基、ベン
ジル、フエネチルなどのアラルキル基、フエニ
ル、ナフチル、アンスリルなどのアリール基を示
し、これらのアルキル基、アラルキル基、アリー
ル基は置換基を有してもよく、置換基としてはメ
チル、エチルなどのアルキル基、塩素原子、臭素
原子などのハロゲン原子、メトキシ、エトキシな
どのアルコキシ基、フエノキシなどのアリールオ
キシ基、ジメチルアミノ、ジエチルアミノなどの
アルキルアミノ基、メチルチオ、エチルチオなど
のアルキルチオ基などが挙げられる。
さらにR5とR6は環を形成してもよい。
前記一般式で表わされるインドリン化合物の代
表的な具体例を次に列挙する。
ただし、前記一般式で表わされるインドリン化
合物は、これに限定されるものではない。
本発明の電子写真感光体は前記一般式で表わさ
れるインドリン化合物を１種または２種以上含有
する感光層を有する。
電子写真感光体の感光層の形態としては種々存
在するが、本発明電子写真感光体の感光層として
は、そのいずれであつてもよい。
例として第１図、第２図、第３図に本発明電子
写真感光体の構成を示す部分断面図を示した。
第１図の電子写真感光体は、導電性支持体１の
上に前記一般式で表わされるインドリン化合物
（以下インドリン化合物という）、増感染料あるい
は電子吸引性化合物およびバインダーよりなる感
光層２を設けたものである。
第２図の電子写真感光体は、導電性支持体１の
上に電荷担体発生物質３をインドリン化合物とバ
インダーからなる電荷移動媒体４の中に分散せし
めた感光層２′を設けたものである。
第３図の電子写真感光体は、導電性支持体１の
上に電荷担体発生層５とインドリン化合物を含む
電荷移動層４からなる感光層２″を設けたもので
ある。
第１図の電子写真感光体において、インドリン
化合物は光導電性物質として作用し、光減衰に必
要な電荷担体の生成および移動はインドリン化合
物を介して行なわれる。多くのインドリン化合物
の吸収は紫外部から可視部低波長にあるため、可
視光で画像形成させるためには、可視領域に吸収
を有する増感染料を添加するか、あるいは電子吸
引性化合物を加え、電荷移動錯体を形成させて増
感する必要がある。
第２図、第３図の電子写真感光体では、電荷担
体発生物質が光に対し電荷担体を発生し、電荷移
動媒体（主にインドリン化合物が働く）により電
荷担体の移動が行なわれる。
第１図の電子写真感光体の作成にはインドリン
化合物をバインダーと共に溶剤中に溶解し、必要
に応じて増感染料あるいは電子吸引性化合物を添
加、導電性支持体上に塗布、乾燥する。
第２図の電子写真感光体の作成にはインドリン
化合物とバインダーを溶解した溶液に電荷担体発
生物質の微粒子を分散させ、これを導電性支持体
上に塗布、乾燥する。
第３図の電子写真感光体は、導電性支持体上に
電荷担体発生物質を真空蒸着するか、あるいは電
荷担体発生物質の微粒子を必要に応じてバインダ
ーに溶解した溶媒中に分散して得た分散液を塗
布、乾燥し、その上にインドリン化合物およびバ
インダーを溶解した溶液を塗布、乾燥して作成さ
れる。塗布には、通常ロールコーター、ワイヤー
バー、ドクターブレードなどを用いる。
感光層の厚さは、第１図および第２図の場合、
３〜50μ、好ましくは５〜20μである。
また第３図の場合は、電荷担体発生層の厚さは
0.5〜5μ、好ましくは１〜2μであり、電荷移動層
の厚さは３〜50μ、好ましくは５〜20μである。
第１図の電子写真感光体において、感光層中の
インドリン化合物の割合は、感光層に対して10〜
70重量％、好ましくは30〜50重量％である。また
可視領域に感光性を与えるために用いる増感染料
は、感光層に対して0.1〜５重量％、好ましくは
0.5〜３重量％である。電子吸引性化合物の添加
は、感光層に対して0.1〜50重量％、好ましくは
５〜30重量％である。
第２図の電子写真感光体において、感光層中の
インドリン化合物の割合は感光層に対して10〜90
重量％、好ましくは10〜60重量％であり、また電
荷担体発生物質は感光層に対して１〜50重量％、
好ましくは３〜20重量％である。
第３図の電子写真感光体における電荷移動層中
のインドリン化合物の割合は、10〜95重量％、好
ましくは10〜60重量％である。
なお、第１〜３図のいずれの電子写真感光体の
作成においても、結合剤とともに可塑剤、増感剤
を用いることができる。
本発明の電子写真感光体において導電性支持体
には、例えばアルミニウムなどの金属板または金
属箔、アルミニウムなどの金属を蒸着したプラス
チツクフイルムあるいは導電処理を施した紙など
が用いられる。
バインダーとしては、ポリスチレン、ポリアク
リルアミド、ポリ−Ｎ−ビニルカルバゾールのよ
うなビニル重合体やポリアミド、ポリエステル、
エポキシ樹脂、フエノキシ樹脂、ポリカーボネー
トなどの縮合樹脂などが用いられるが、絶縁性で
支持体に対する接着性のある樹脂はすべて使用で
きる。
前記感光層に用いられる増感染料、電子吸引性
化合物、電荷担体発生物質としてはいずれも周知
のものが使用できる。
増感染料としては、例えばメチルバイオレツ
ト、ブリリアントグリーン、クリスタルバイオレ
ツトなどのトリフエニルメタン染料、メチレンブ
ルーなどのチアジン染料、シアニン染料、ピリリ
ウム染料などが挙げられる。
電子吸引性化合物としては、例えばクロルアニ
ル、１−ニトロアントラキノン、２−クロルアン
トラキノンなどのキノン類、２−クロルベンズア
ルデヒド、４−ニトロベンズアルデヒドなどのア
ルデヒド類、３，５−ジニトロベンゾフエノン、
２，４，７−トリニトロフルオレノン、２，４，
５，７−テトラニトロフルオレノンなどのケトン
類、無水フタル酸など酸無水物、シアノ化合物な
どが挙げられる。
電荷担体発生物質としてはセレン、セレン−テ
ルル合金、セレン−ヒ素合金、硫化カドミウムな
どの無機系光導電性物質、銅フタロシアニン、ア
ゾ系顔料、ジスアゾ系顔料、トリスアゾ系顔料、
シアニン系顔料、アントラキノン系顔料、ペリレ
ン系顔料、ピリリウム塩類、チオインジゴ、キナ
クリドンなどの有機光導電性物質が挙げられる。
さらに感光体の成膜性、可撓性、機械的強度を
向上するために周知の可塑剤を含有してもよい。
可塑剤としてはフタル酸エステル、リン酸エス
テル、ハロゲン化パラフイン、メチルナフタリン
などの芳香族化合物が挙げられる。
さらに上記のようにして作成される電子写真感
光体には、導電性支持体と感光層の間に、必要に
応じた接着層またはバリヤ層を設けることができ
る。これらの層の材料としてはポリアミド、ニト
ロセルロース、酸化アルミニウムなどであり、そ
の膜厚は1μ以下が望ましい。
本発明の電子写真感光体は感度が非常に高く、
繰り返し使用による残留電位の蓄積や表面電位お
よび感度の変動が小さく、耐久性に優れ、可撓性
に富むなどの優れた利点を有する。
特に、画質が繰り返し耐久後もボケなどを発生
せず、高画質、高耐久性である。
［実施例］
実施例 １
クロルダイアンブルーを２部、
ポリエステル（イソプタル酸−エチレングリコ
ール縮合体、Mn＝30000）を１部、テトラヒド
ロフランを97部、
上記成分をボールミル中で粉砕、混合して電荷
担体発生物質分散液を得た。これをアルミノウム
蒸着したポリエステルフイルム上にワイヤーバー
で塗布、乾燥し、厚さ1μの電荷担体発生層を形
成した。この電荷担体発生層の上に前記例示化合
物(10)のインドリン化合物を10部、ポリカーボネー
ト（ビスフエノールＡ−ホスゲン縮合体、Mn＝
28000）を10部をテトラヒドロフラン80部に溶解
させた塗布液を乾燥後の膜厚が15μとなるように
塗布して電荷移動層を形成し、電子写真感光体を
作成した。感光体(1)とする。
感光体(1)について、市販の静電複写紙試験装置
（KK川口電気製作所製SP428）を用いて−5KV
前後のコロナ放電を20秒間行なつて帯電させた
後、20秒間暗所に放置し、その時の表面電位を
600Vとし、次いでタングステンランプ光を感光
体表面の照度が10ルツクスになるように照射して
その表面電位が300Vになるまでの時間（秒）を
求め、露光感度Ｅ1/2（ルツクス、秒）を算出し
た。結果を後記する。
この感光体(1)を電子写真複写機（商品名NP−
3525、キヤノン(株)製）にセツトし、原稿の複写を
行なつたところ、10000枚耐久後も画像上ボケ、
カブリのない高解像度で高画質の画像が得られ
た。
実施例 ２〜11
電荷担体発生物質（後記例）およびインドリン
化合物を後記した組合せに代えた他は実施例１と
全く同様にして電子写真感光体を作成した。
これを感光体(2)〜(11)とする。
実施例１と同様に露光感度Ｅ1/2（ルツクス、
秒）を測定した。結果を後記する。
さらに感光体(2)〜(11)を実施例１と同様に電子写
真複写機にて原稿の複写を行なつた。
10000枚耐久後も画像上ボケ、カブリのない、
高解像度で高画質の画像が得られた。
実施例２〜11で使用の電荷担体発生物質
[Industrial Field of Application] The present invention relates to an electrophotographic photoreceptor, and more particularly to an electrophotographic photoreceptor having a photosensitive layer containing an indoline compound on a conductive support. [Prior Art] Conventionally, inorganic photoconductive substances such as selenium, cadmium sulfide, and zinc oxide have been widely used in the photosensitive layer of electrophotographic photoreceptors. In recent years, research on organic photoconductive materials has progressed, and some have been put into practical use as electrophotographic photoreceptors. Organic photoconductive substances have advantages over inorganic photoconductive substances in that they are lightweight, easy to form into films, and easy to manufacture photoreceptors. Many studies have been conducted on photoconductive polymers such as polyvinylcarbazole as organic photoconductive substances, but these polymers alone have poor film properties, flexibility, and adhesion, and it is difficult to improve these shortcomings. For this purpose, plasticizers, binders, etc. are added, but these tend to cause other problems such as a decrease in sensitivity and an increase in residual potential, making it extremely difficult to put them into practical use. On the other hand, for organic low-molecular photoconductive substances, if a polymer with excellent film properties, flexibility, and adhesive properties is selected as a binder, a photoreceptor with excellent mechanical properties can be easily obtained. It has been difficult to find compounds suitable for making highly sensitive photoreceptors. In addition, low-molecular stilbene compounds described in JP-A-59-151157 exhibit high sensitivity initially, but when attached to a copying machine and repeatedly outputting images, the stilbene compounds cause ozonation and photodeterioration. As a result, the image quality deteriorates and only blurred images are obtained. [Problems to be Solved by the Invention] The purpose of the present invention is to eliminate the various drawbacks of the conventional photoreceptors mentioned above, and to meet the requirements of electrophotographic photoreceptors such as high sensitivity, high durability, and high modification. Every time,
An object of the present invention is to provide an electrophotographic photoreceptor that fully satisfies all conditions for high image quality. [Means for Solving Problems and Effects] The present invention comprises an electrophotographic photoreceptor characterized in that a photosensitive layer containing an indoline compound represented by the following general formula is provided on a conductive support. general formula In the formula, A represents a hydrogen atom, an aliphatic hydrocarbon group, an aromatic hydrocarbon group which may have a substituent, or an aromatic heterocyclic group, R 1 , R 2 , R 3 , R 4 , R 5 and R6
each independently represents a hydrogen atom, a halogen atom, a nitro group, an alkyl group that may have a substituent, an aralkyl group, or an aryl group, and R 5 and
R 6 may form a ring. The present invention will be specifically explained below. The electrophotographic photoreceptor of the present invention contains an indoline compound represented by the above general formula in the photosensitive layer. In the general formula, A is a hydrogen atom, methyl,
Ethyl, linear or branched alkyl groups such as propyl, butyl, pentyl, benzene, naphthalene, anthracene, pyrene, acenaphthene,
These are aromatic hydrocarbon groups derived from fluorene, etc., and aromatic heterocyclic groups derived from pyridine, pyrrole, pyrazole, dibenzofuran, carbazole, etc., and these aromatic hydrocarbon groups and aromatic heterocyclic groups are substituents. Substituents include alkyl groups such as methyl and ethyl, halogen atoms such as chlorine and bromine, alkoxy groups such as methoxy and ethoxy, aryloxy groups such as phenoxy, and dimethylamino and diethylamino. alkylamino group, methylthio,
Examples include alkylthio groups such as ethylthio. R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are hydrogen atoms, halogen atoms such as chlorine atoms, bromine atoms, nitro groups, methyl, ethyl, linear or branched propyl, butyl, pentyl , aralkyl groups such as benzyl, phenethyl, and aryl groups such as phenyl, naphthyl, and anthryl. These alkyl groups, aralkyl groups, and aryl groups may have a substituent, and the substituent is methyl. , alkyl groups such as ethyl, halogen atoms such as chlorine atom and bromine atom, alkoxy groups such as methoxy and ethoxy, aryloxy groups such as phenoxy, alkylamino groups such as dimethylamino and diethylamino, alkylthio groups such as methylthio and ethylthio, etc. can be mentioned. Furthermore, R 5 and R 6 may form a ring. Typical specific examples of the indoline compound represented by the above general formula are listed below. However, the indoline compound represented by the above general formula is not limited thereto. The electrophotographic photoreceptor of the present invention has a photosensitive layer containing one or more indoline compounds represented by the above general formula. There are various forms of the photosensitive layer of the electrophotographic photoreceptor, and the photosensitive layer of the electrophotographic photoreceptor of the present invention may be any of them. As examples, FIGS. 1, 2, and 3 are partial sectional views showing the structure of the electrophotographic photoreceptor of the present invention. In the electrophotographic photoreceptor shown in FIG. 1, a photosensitive layer 2 comprising an indoline compound represented by the above general formula (hereinafter referred to as an indoline compound), a sensitizing dye or an electron-withdrawing compound, and a binder is provided on a conductive support 1. It is something that The electrophotographic photoreceptor shown in FIG. 2 has a photosensitive layer 2' on a conductive support 1, in which a charge carrier generating substance 3 is dispersed in a charge transfer medium 4 made of an indoline compound and a binder. . The electrophotographic photoreceptor shown in FIG. 3 has a photosensitive layer 2'' consisting of a charge carrier generation layer 5 and a charge transfer layer 4 containing an indoline compound on a conductive support 1. In a photographic photoreceptor, an indoline compound acts as a photoconductive substance, and the generation and transfer of charge carriers necessary for light attenuation occur through the indoline compound.The absorption of many indoline compounds occurs at low wavelengths in the ultraviolet to visible range. Therefore, in order to form an image with visible light, it is necessary to add a sensitizing dye that absorbs in the visible region or to add an electron-withdrawing compound to form a charge transfer complex to sensitize. In the electrophotographic photoreceptor shown in FIGS. 2 and 3, a charge carrier generating substance generates charge carriers in response to light, and the charge carriers are transferred by a charge transfer medium (mainly an indoline compound). To create the electrophotographic photoreceptor shown in the figure, an indoline compound and a binder are dissolved in a solvent, a sensitizing dye or an electron-withdrawing compound is added as needed, and the material is coated on a conductive support and dried. To create the electrophotographic photoreceptor shown in FIG. A charge carrier generating substance is vacuum deposited on a conductive support, or a dispersion obtained by dispersing fine particles of a charge carrier generating substance in a solvent dissolved in a binder as necessary is coated, dried, and It is created by coating a solution containing an indoline compound and a binder on top and drying it.A roll coater, wire bar, doctor blade, etc. is usually used for coating.The thickness of the photosensitive layer is shown in Figures 1 and 2. In the case of the figure,
It is 3-50μ, preferably 5-20μ. In the case of Figure 3, the thickness of the charge carrier generation layer is
The thickness of the charge transfer layer is 0.5-5μ, preferably 1-2μ, and the thickness of the charge transport layer is 3-50μ, preferably 5-20μ. In the electrophotographic photoreceptor shown in FIG. 1, the ratio of the indoline compound in the photosensitive layer is 10 to
70% by weight, preferably 30-50% by weight. The sensitizing dye used to impart photosensitivity in the visible region is preferably 0.1 to 5% by weight based on the photosensitive layer.
It is 0.5 to 3% by weight. The electron-withdrawing compound is added in an amount of 0.1 to 50% by weight, preferably 5 to 30% by weight, based on the photosensitive layer. In the electrophotographic photoreceptor shown in Figure 2, the ratio of the indoline compound in the photosensitive layer is 10 to 90% of the photosensitive layer.
% by weight, preferably 10 to 60% by weight, and the charge carrier generating substance is 1 to 50% by weight, based on the photosensitive layer.
Preferably it is 3 to 20% by weight. The proportion of the indoline compound in the charge transfer layer in the electrophotographic photoreceptor shown in FIG. 3 is 10 to 95% by weight, preferably 10 to 60% by weight. In addition, in producing any of the electrophotographic photoreceptors shown in FIGS. 1 to 3, a plasticizer and a sensitizer can be used together with a binder. In the electrophotographic photoreceptor of the present invention, the conductive support may be, for example, a metal plate or foil made of aluminum or the like, a plastic film deposited with a metal such as aluminum, or paper subjected to conductive treatment. As a binder, vinyl polymers such as polystyrene, polyacrylamide, poly-N-vinylcarbazole, polyamide, polyester,
Condensation resins such as epoxy resins, phenoxy resins, and polycarbonates are used, but any resin that is insulating and adhesive to the support can be used. As the sensitizing dye, electron-withdrawing compound, and charge carrier generating substance used in the photosensitive layer, well-known ones can be used. Examples of the sensitizing dye include triphenylmethane dyes such as methyl violet, brilliant green, and crystal violet, thiazine dyes such as methylene blue, cyanine dyes, and pyrylium dyes. Examples of electron-withdrawing compounds include quinones such as chloranil, 1-nitroanthraquinone, and 2-chloroanthraquinone, aldehydes such as 2-chlorobenzaldehyde and 4-nitrobenzaldehyde, 3,5-dinitrobenzophenone,
2,4,7-trinitrofluorenone, 2,4,
Examples include ketones such as 5,7-tetranitrofluorenone, acid anhydrides such as phthalic anhydride, and cyano compounds. Charge carrier generating substances include selenium, selenium-tellurium alloys, selenium-arsenic alloys, inorganic photoconductive substances such as cadmium sulfide, copper phthalocyanine, azo pigments, disazo pigments, trisazo pigments,
Examples include organic photoconductive substances such as cyanine pigments, anthraquinone pigments, perylene pigments, pyrylium salts, thioindigo, and quinacridone. Furthermore, a well-known plasticizer may be contained in order to improve the film formability, flexibility, and mechanical strength of the photoreceptor. Examples of plasticizers include aromatic compounds such as phthalic esters, phosphoric esters, halogenated paraffins, and methylnaphthalene. Further, in the electrophotographic photoreceptor produced as described above, an adhesive layer or a barrier layer can be provided between the conductive support and the photosensitive layer, if necessary. Materials for these layers include polyamide, nitrocellulose, aluminum oxide, etc., and the film thickness is preferably 1 μm or less. The electrophotographic photoreceptor of the present invention has extremely high sensitivity;
It has excellent advantages such as small accumulation of residual potential and small fluctuations in surface potential and sensitivity due to repeated use, excellent durability, and high flexibility. In particular, the image quality is high and durable, with no blurring even after repeated durability tests. [Example] Example 1 2 parts of Chlordiane Blue, 1 part of polyester (isoptalic acid-ethylene glycol condensate, Mn=30000), 97 parts of tetrahydrofuran, and the above components were ground and mixed in a ball mill to obtain a charge carrier generating material dispersion. This was applied with a wire bar onto a polyester film on which aluminum was vapor-deposited, and dried to form a charge carrier generation layer with a thickness of 1 μm. On this charge carrier generation layer, 10 parts of the indoline compound of the above-mentioned exemplary compound (10) and polycarbonate (bisphenol A-phosgene condensate, Mn=
A charge transfer layer was formed by coating a coating solution prepared by dissolving 10 parts of 28000) in 80 parts of tetrahydrofuran so that the film thickness after drying was 15 μm, and an electrophotographic photoreceptor was prepared. Let it be a photoreceptor (1). The photoreceptor (1) was tested at -5KV using a commercially available electrostatic copying paper testing device (KK Kawaguchi Electric Seisakusho SP428).
After charging by corona discharge for 20 seconds before and after, leave it in a dark place for 20 seconds and measure the surface potential at that time.
600V, then irradiate the photoreceptor surface with tungsten lamp light so that the illumination intensity is 10 lux, find the time (seconds) until the surface potential reaches 300V, and find the exposure sensitivity E1/2 (lux, seconds). Calculated. The results will be described later. This photoreceptor (1) is used in an electrophotographic copying machine (product name NP-).
3525 (manufactured by Canon Inc.) to copy a document, the image was blurry even after 10,000 copies.
High-resolution, high-quality images with no fog were obtained. Examples 2 to 11 Electrophotographic photoreceptors were prepared in exactly the same manner as in Example 1, except that the charge carrier generating substances (examples described later) and indoline compounds were replaced with the combinations described later. These are referred to as photoreceptors (2) to (11). As in Example 1, the exposure sensitivity E1/2 (lux,
seconds) was measured. The results will be described later. Further, original copies were made using the photoreceptors (2) to (11) using an electrophotographic copying machine in the same manner as in Example 1. No blur or fog on the image even after 10,000 sheets of durability.
High resolution and high quality images were obtained. Charge carrier generating material used in Examples 2 to 11
【表】
比較例 １
インドリン化合物を下記の化合物に代えた他は
実施例１と同様にして電子写真感光体を作成し、
これを感光体(12)とする。
実施例１と同様に露光感度Ｅ1/2（ルツクス、
秒）を測定した。結果を後記する。
さらに感光体(12)を実施例１と同様に電子写真複
写機にて原稿の複写を行なつたところ、2000枚耐
久後には画像上ボケが発生し、高解像度の画像は
得られなくなつた。
比較例 ２
インドリン化合物を下記の化合物を代えた他は
実施例１と同様にして電子写真感光体を作成し、
これを感光体(13)とする。
実施例１と同様に露光感度Ｅ1/2（ルツクス、
秒）を測定した。結果を後記する。
さらに感光体(13)を実施例１と同様に電子写真複
写機にて原稿の複写を行なつたところ、1000枚耐
久後には画像上ボケ、カブリが発生し、高解像度
の画像は得られなくなつた。
以下に上記実施例１〜11および比較例１〜２に
おいて測定した測定結果を示す。[Table] Comparative Example 1 An electrophotographic photoreceptor was prepared in the same manner as in Example 1 except that the indoline compound was replaced with the following compound.
This will be referred to as a photoreceptor (12). As in Example 1, the exposure sensitivity E1/2 (lux,
seconds) was measured. The results will be described later. Furthermore, when the photoreceptor (12) was used to copy an original using an electrophotographic copying machine in the same manner as in Example 1, blurring occurred on the image after 2,000 copies, and high-resolution images could no longer be obtained. . Comparative Example 2 An electrophotographic photoreceptor was prepared in the same manner as in Example 1 except that the indoline compound was replaced with the following compound,
This is referred to as a photoreceptor (13). As in Example 1, the exposure sensitivity E1/2 (lux,
seconds) was measured. The results will be described later. Furthermore, when the photoreceptor (13) was used to copy an original using an electrophotographic copying machine in the same manner as in Example 1, blurring and fogging occurred on the image after 1000 copies, and high-resolution images could not be obtained. Summer. The measurement results measured in Examples 1 to 11 and Comparative Examples 1 to 2 are shown below.
【表】
［発明の効果］
以上詳細に説明したように本発明の電子写真感
光体は、特定のインドリン化合物を感光層に含有
せしめたことにより、感度が非常に高く、さらに
驚くべきことに繰り返し耐久した後でも画像上ボ
ケ、カブリのない高解像度で高画質の画像を得る
ことができる。[Table] [Effects of the Invention] As explained in detail above, the electrophotographic photoreceptor of the present invention has extremely high sensitivity due to the inclusion of a specific indoline compound in the photosensitive layer. Even after durability, it is possible to obtain high-resolution, high-quality images without blur or fog.
第１図は本発明電子写真感光体の構成を示す部
分断面図、第２図および第３図はそれぞれ本発明
電子写真感光体の他の構成を示す部分断面図であ
る。
符号１は導電性支持体、２，２′および２″は感
光層、３は電荷担体発生物質、４は電荷移動層、
５は電荷担体発生層を示す。
FIG. 1 is a partial sectional view showing the structure of the electrophotographic photoreceptor of the present invention, and FIGS. 2 and 3 are partial sectional views showing other structures of the electrophotographic photoreceptor of the invention. 1 is a conductive support, 2, 2' and 2'' are photosensitive layers, 3 is a charge carrier generating material, 4 is a charge transport layer,
5 represents a charge carrier generation layer.
Claims (1)
ンドリン化合物を含有する感光層を設けたことを
特徴とする電子写真感光体。 一般式 式中、Ａは水素原子、脂肪族炭化水素基、置換
基を有してもよい芳香族炭化水素基または芳香族
複素環基を示し、R1，R2，R3，R4，R5およびR6
はそれぞれ独立に水素原子、ハロゲン原子、ニト
ロ基、置換基を有してもよいアルキル基、アラル
キル基あるいはアリール基を示し、また、R5と
R6は環を形成してもよい。[Scope of Claims] 1. An electrophotographic photoreceptor comprising a photosensitive layer containing an indoline compound represented by the following general formula on a conductive support. general formula In the formula, A represents a hydrogen atom, an aliphatic hydrocarbon group, an aromatic hydrocarbon group which may have a substituent, or an aromatic heterocyclic group, R 1 , R 2 , R 3 , R 4 , R 5 and R6
each independently represents a hydrogen atom, a halogen atom, a nitro group, an alkyl group that may have a substituent, an aralkyl group, or an aryl group, and R 5 and
R 6 may form a ring.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5288087A JPS63220159A (en) | 1987-03-10 | 1987-03-10 | Electrophotographic sensitive body |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5288087A JPS63220159A (en) | 1987-03-10 | 1987-03-10 | Electrophotographic sensitive body |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63220159A JPS63220159A (en) | 1988-09-13 |
| JPH0516020B2 true JPH0516020B2 (en) | 1993-03-03 |
Family
ID=12927195
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5288087A Granted JPS63220159A (en) | 1987-03-10 | 1987-03-10 | Electrophotographic sensitive body |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63220159A (en) |
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Also Published As
| Publication number | Publication date |
|---|---|
| JPS63220159A (en) | 1988-09-13 |
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