JPS63180954A - Electrophotographic sensitive body - Google Patents
Electrophotographic sensitive bodyInfo
- Publication number
- JPS63180954A JPS63180954A JP62012967A JP1296787A JPS63180954A JP S63180954 A JPS63180954 A JP S63180954A JP 62012967 A JP62012967 A JP 62012967A JP 1296787 A JP1296787 A JP 1296787A JP S63180954 A JPS63180954 A JP S63180954A
- Authority
- JP
- Japan
- Prior art keywords
- charge
- photoreceptor
- alkyl
- photosensitive layer
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000126 substance Substances 0.000 claims abstract description 26
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 3
- 125000003118 aryl group Chemical group 0.000 claims abstract description 3
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 3
- 125000005843 halogen group Chemical group 0.000 claims abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
- 108091008695 photoreceptors Proteins 0.000 claims description 48
- -1 amino compound Chemical class 0.000 claims description 25
- 239000004480 active ingredient Substances 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 abstract description 15
- 239000002800 charge carrier Substances 0.000 abstract description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 9
- 238000004519 manufacturing process Methods 0.000 abstract description 7
- 230000001235 sensitizing effect Effects 0.000 abstract description 7
- 230000035939 shock Effects 0.000 abstract description 3
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 54
- 239000000049 pigment Substances 0.000 description 16
- 230000032258 transport Effects 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000000975 dye Substances 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 238000000034 method Methods 0.000 description 7
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 239000010419 fine particle Substances 0.000 description 6
- 229910052711 selenium Inorganic materials 0.000 description 6
- 239000011669 selenium Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- WUPHOULIZUERAE-UHFFFAOYSA-N 3-(oxolan-2-yl)propanoic acid Chemical compound OC(=O)CCC1CCCO1 WUPHOULIZUERAE-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910052980 cadmium sulfide Inorganic materials 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000012860 organic pigment Substances 0.000 description 3
- 239000004014 plasticizer Substances 0.000 description 3
- 229920001225 polyester resin Polymers 0.000 description 3
- 239000004645 polyester resin Substances 0.000 description 3
- 239000006163 transport media Substances 0.000 description 3
- QNLZIZAQLLYXTC-UHFFFAOYSA-N 1,2-dimethylnaphthalene Chemical compound C1=CC=CC2=C(C)C(C)=CC=C21 QNLZIZAQLLYXTC-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical compound O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 239000011147 inorganic material Substances 0.000 description 2
- 239000001023 inorganic pigment Substances 0.000 description 2
- SXQCTESRRZBPHJ-UHFFFAOYSA-M lissamine rhodamine Chemical compound [Na+].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=C(S([O-])(=O)=O)C=C1S([O-])(=O)=O SXQCTESRRZBPHJ-UHFFFAOYSA-M 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 2
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical class C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 2
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 2
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 2
- 229910052721 tungsten Inorganic materials 0.000 description 2
- 239000010937 tungsten Substances 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- NGQSLSMAEVWNPU-YTEMWHBBSA-N 1,2-bis[(e)-2-phenylethenyl]benzene Chemical group C=1C=CC=CC=1/C=C/C1=CC=CC=C1\C=C\C1=CC=CC=C1 NGQSLSMAEVWNPU-YTEMWHBBSA-N 0.000 description 1
- NGZUCVGMNQGGNA-UHFFFAOYSA-N 7-[5-(2-acetamidoethyl)-2-hydroxyphenyl]-3,5,6,8-tetrahydroxy-9,10-dioxoanthracene-1,2-dicarboxylic acid 7-[5-(2-amino-2-carboxyethyl)-2-hydroxyphenyl]-3,5,6,8-tetrahydroxy-9,10-dioxoanthracene-1,2-dicarboxylic acid 3,5,6,8-tetrahydroxy-7-[2-hydroxy-5-(2-hydroxyethyl)phenyl]-9,10-dioxoanthracene-1,2-dicarboxylic acid 3,6,8-trihydroxy-1-methyl-9,10-dioxoanthracene-2-carboxylic acid Chemical compound Cc1c(C(O)=O)c(O)cc2C(=O)c3cc(O)cc(O)c3C(=O)c12.OCCc1ccc(O)c(c1)-c1c(O)c(O)c2C(=O)c3cc(O)c(C(O)=O)c(C(O)=O)c3C(=O)c2c1O.CC(=O)NCCc1ccc(O)c(c1)-c1c(O)c(O)c2C(=O)c3cc(O)c(C(O)=O)c(C(O)=O)c3C(=O)c2c1O.NC(Cc1ccc(O)c(c1)-c1c(O)c(O)c2C(=O)c3cc(O)c(C(O)=O)c(C(O)=O)c3C(=O)c2c1O)C(O)=O NGZUCVGMNQGGNA-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 235000000177 Indigofera tinctoria Nutrition 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- 239000004419 Panlite Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- JSQFXMIMWAKJQJ-UHFFFAOYSA-N [9-(2-carboxyphenyl)-6-(ethylamino)xanthen-3-ylidene]-diethylazanium;chloride Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(NCC)=CC=C2C=1C1=CC=CC=C1C(O)=O JSQFXMIMWAKJQJ-UHFFFAOYSA-N 0.000 description 1
- SRKRSWKCLVMJRZ-UHFFFAOYSA-N [S-2].S.[SeH2].[Cd+2] Chemical compound [S-2].S.[SeH2].[Cd+2] SRKRSWKCLVMJRZ-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 239000004840 adhesive resin Substances 0.000 description 1
- 229920006223 adhesive resin Polymers 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 238000005452 bending Methods 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
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- MRQIXHXHHPWVIL-UHFFFAOYSA-N chembl1397023 Chemical compound OC1=CC=C2C=CC=CC2=C1N=NC1=CC=CC=C1 MRQIXHXHHPWVIL-UHFFFAOYSA-N 0.000 description 1
- VYXSBFYARXAAKO-WTKGSRSZSA-N chembl402140 Chemical compound Cl.C1=2C=C(C)C(NCC)=CC=2OC2=C\C(=N/CC)C(C)=CC2=C1C1=CC=CC=C1C(=O)OCC VYXSBFYARXAAKO-WTKGSRSZSA-N 0.000 description 1
- JPBGLQJDCUZXEF-UHFFFAOYSA-N chromenylium Chemical class [O+]1=CC=CC2=CC=CC=C21 JPBGLQJDCUZXEF-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 150000001875 compounds Chemical class 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
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- YQGOJNYOYNNSMM-UHFFFAOYSA-N eosin Chemical compound [Na+].OC(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C(O)=C(Br)C=C21 YQGOJNYOYNNSMM-UHFFFAOYSA-N 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- IINNWAYUJNWZRM-UHFFFAOYSA-L erythrosin B Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=CC=C1C1=C2C=C(I)C(=O)C(I)=C2OC2=C(I)C([O-])=C(I)C=C21 IINNWAYUJNWZRM-UHFFFAOYSA-L 0.000 description 1
- 230000005496 eutectics Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical group C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229940097275 indigo Drugs 0.000 description 1
- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 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
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-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
- 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
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 150000003071 polychlorinated biphenyls Chemical class 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 229920001470 polyketone Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920006215 polyvinyl ketone Polymers 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 229940043267 rhodamine b Drugs 0.000 description 1
- 229940081623 rose bengal Drugs 0.000 description 1
- 229930187593 rose bengal Natural products 0.000 description 1
- AZJPTIGZZTZIDR-UHFFFAOYSA-L rose bengal Chemical compound [K+].[K+].[O-]C(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C1=C2C=C(I)C(=O)C(I)=C2OC2=C(I)C([O-])=C(I)C=C21 AZJPTIGZZTZIDR-UHFFFAOYSA-L 0.000 description 1
- STRXNPAVPKGJQR-UHFFFAOYSA-N rose bengal A Natural products O1C(=O)C(C(=CC=C2Cl)Cl)=C2C21C1=CC(I)=C(O)C(I)=C1OC1=C(I)C(O)=C(I)C=C21 STRXNPAVPKGJQR-UHFFFAOYSA-N 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- AXMCIYLNKNGNOT-UHFFFAOYSA-M sodium;3-[[4-[(4-dimethylazaniumylidenecyclohexa-2,5-dien-1-ylidene)-[4-[ethyl-[(3-sulfonatophenyl)methyl]amino]phenyl]methyl]-n-ethylanilino]methyl]benzenesulfonate Chemical compound [Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](C)C)C=2C=CC(=CC=2)N(CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 AXMCIYLNKNGNOT-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- 239000001016 thiazine dye Substances 0.000 description 1
- 239000001003 triarylmethane dye Substances 0.000 description 1
- 125000006617 triphenylamine group Chemical group 0.000 description 1
- LLWJPGAKXJBKKA-UHFFFAOYSA-N victoria blue B Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1C(C=1C=CC(=CC=1)N(C)C)=C(C=C1)C2=CC=CC=C2C1=[NH+]C1=CC=CC=C1 LLWJPGAKXJBKKA-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229940075420 xanthine Drugs 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
- G03G5/0601—Acyclic or carbocyclic compounds
- G03G5/0612—Acyclic or carbocyclic compounds containing nitrogen
- G03G5/0614—Amines
- G03G5/06142—Amines arylamine
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Photoreceptors In Electrophotography (AREA)
Abstract
Description
【発明の詳細な説明】
艮監分互
本発明は電子写真用感光体に関し、詳しくは感光層中に
特定のアミノ化合物を含有させた電子写真用感光体に関
する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to an electrophotographic photoreceptor, and more particularly to an electrophotographic photoreceptor containing a specific amino compound in its photosensitive layer.
災来１権
従来、電子写真方式において使用される感光体の光導電
性素材として用いられているものにセレン、硫化カドミ
ウム、酸化亜鉛などの無機物質がある。ここにいう「電
子写真方式」とは、一般に、光導電性の感光体をまず暗
所で、例えばコロナ放電によって帯電せしめ１次いで像
露光し、露光部のみの電荷を選択的に逸散せしめて静電
潜像を得、この潜像部を染料、顔料などの着色材と高分
子物質などの結合剤とから構成される検電微粒子（トナ
ー）で現像し可視化して画像を形成するようにした画像
形成法の一つである。Conventionally, inorganic materials such as selenium, cadmium sulfide, and zinc oxide have been used as photoconductive materials for photoreceptors used in electrophotography. The "electrophotographic method" referred to here generally means that a photoconductive photoreceptor is first charged in a dark place by, for example, corona discharge, and then imagewise exposed to light to selectively dissipate the charge only in the exposed areas. An electrostatic latent image is obtained, and this latent image area is developed and visualized using electrostatic fine particles (toner) composed of a coloring material such as a dye or pigment and a binder such as a polymeric substance to form an image. This is one of the image forming methods.
このような電子写真法において感光体に要求される基本
的な特性としては、（１）暗所で適当な電位に帯電でき
ること、（２）暗所において電荷の逸散が少ないこと、
（３）光照射によって速・ やかに電荷を逸散せしめう
ろことなどがあげられる。The basic characteristics required of a photoreceptor in such an electrophotographic method are (1) ability to be charged to an appropriate potential in a dark place, (2) less dissipation of charge in a dark place,
(3) Examples include scales that quickly dissipate charge when irradiated with light.
ところで、前記の無機物質はそれぞれが多くの長所をも
っていると同時に、さまざまな欠点をも有しているのが
事実である０例えば、現在広く用いられているセレンは
前記（１）〜（３）の条件は十分に満足するが、製造す
る条件がむずかしく、製造コストが高くなり、可撓性が
なく、ベルト状に加工することがむずかしく、熱や機械
的の衝撃に鋭敏なため取扱いに注意を要するなどの欠点
もある。硫化カドミウムや酸化亜鉛は、結合剤としての
樹脂に分散させて感光体として用いられているが、平滑
性、硬度、引張り強度、耐摩擦性などの機械的な欠点が
あるためにそのままでは反復して使用することができな
い。By the way, it is true that each of the above-mentioned inorganic substances has many advantages, but also various disadvantages.For example, selenium, which is currently widely used, has the above-mentioned (1) to (3). Although it fully satisfies the above conditions, the manufacturing conditions are difficult, the manufacturing cost is high, it is not flexible, it is difficult to process it into a belt shape, and it is sensitive to heat and mechanical shock, so it must be handled with care. There are also drawbacks such as the need for Cadmium sulfide and zinc oxide are used as photoreceptors by being dispersed in a resin as a binder, but they cannot be used as is because of mechanical drawbacks such as smoothness, hardness, tensile strength, and abrasion resistance. cannot be used.
近年、これら無機物質の欠点を排除するためにいろいろ
な有機物質を用いた電子写真用感光体が提案され、実用
に供されているものもある。In recent years, electrophotographic photoreceptors using various organic materials have been proposed in order to eliminate the drawbacks of these inorganic materials, and some of them have been put into practical use.
例えば、ポリ−Ｎ−ビニルカルバゾールと２，４゜７−
ドリニトロフルオレンー９−オンとからなる感光体（米
国特許第３，４８４，２３７号明細書に記載）、ポリ−
Ｎ−ビニルカルバゾールをピリリウム塩系色素で増感し
てなる感光体（特公昭４８−２５６５８号公報に記載）
、有機顔料を主成分とする感光体（特開昭４７−３７５
４３号公報に記載）、染料と樹脂とからなる共晶錯体を
主成分とする感光体（特開昭４７−１０７３５号公報に
記載）などである。これらの感光体は優れた特性を有し
ており実用的にも価値が高いと思われるものであるが、
電子写真法において、感光体に対するいろいろな要求を
考慮すると、まだ、これらの要求を十分に満足するもの
が得られていないのが実状である。For example, poly-N-vinylcarbazole and 2,4°7-
A photoreceptor consisting of donitrofluoren-9-one (described in U.S. Pat. No. 3,484,237), poly-
Photoreceptor made by sensitizing N-vinylcarbazole with a pyrylium salt dye (described in Japanese Patent Publication No. 48-25658)
, a photoreceptor whose main component is an organic pigment (Japanese Patent Application Laid-Open No. 47-375
43 (described in Japanese Patent Application Laid-Open No. 1987-10735), and a photoreceptor whose main component is a eutectic complex consisting of a dye and a resin (described in Japanese Patent Application Laid-open No. 10735/1983). These photoreceptors have excellent properties and are considered to be of high practical value; however,
In electrophotography, considering various requirements for photoreceptors, the reality is that no one that fully satisfies these requirements has yet been obtained.
だが、これまでに挙げた感光体は、いずれも目的により
、又は作製方法により違いはあるが、一般的にいってす
ぐれた光導電性物質を使用することによって良好な特性
が得られるものである。However, all of the photoreceptors mentioned so far differ depending on the purpose or manufacturing method, but generally speaking, good characteristics can be obtained by using excellent photoconductive materials. .
本発明者らは、多くの光導電性物質についての研究、検
討を行なった結果、下記一般式（１）で表わされるアミ
ノ化合物
（式中Ｒ″は水素原子、アルキル基、アルコキシ基、ア
リールオキシ基またはハロゲン原子を、 Ｒ２水素原子
、置換アルキル基を含むアルキル基または置換もしくは
無置換のフェニル基を、Ｒ３及びＲ４はアルキル基、ア
ラルキル基またはアリール基を表わし、Ａｒは芳香族炭
化水素を表わす、）
で表わされるアミノ化合物が電子写真用感光体の光導電
性物質として有効に働くことを見出した。更にまた、こ
のアミノ化合物は、後述から明らかなように、いろいろ
の材料と組合わされることによって予期しえない効果を
有する感光体を作成しうろことをも見出した０本発明は
こうした知見に基づいて完成されたものである。As a result of research and examination on many photoconductive substances, the present inventors discovered an amino compound represented by the following general formula (1) (wherein R'' is a hydrogen atom, an alkyl group, an alkoxy group, an aryloxy group or a halogen atom, R2 represents a hydrogen atom, an alkyl group including a substituted alkyl group, or a substituted or unsubstituted phenyl group, R3 and R4 represent an alkyl group, an aralkyl group, or an aryl group, and Ar represents an aromatic hydrocarbon. , ) has been found to work effectively as a photoconductive substance for electrophotographic photoreceptors.Furthermore, as will be clear from the description below, this amino compound can be combined with various materials. The present invention was completed based on these findings.
しかして、本発明の目的は、先に述べた従来の感光体の
もつ種々の欠点を解消し、電子写真法において要求され
る条件を十分満足しうる感光体を提供することにある０
本発明の他の目的は、製造が容易でかつ比較的安価に行
なえ、耐久性にもすぐれた電子写真用感光体を提供する
ことにある。SUMMARY OF THE INVENTION Therefore, it is an object of the present invention to provide a photoreceptor that can overcome the various drawbacks of the conventional photoreceptor described above and fully satisfy the conditions required in electrophotography.
Another object of the present invention is to provide an electrophotographic photoreceptor that is easy to manufacture, relatively inexpensive, and has excellent durability.
即ち、本発明は導電性支持体上に感光層を設けた電子写
真用感光体において、前記感光層中に上記の一般式（Ｉ
）で表わされるアミノ化合物が有効成分として含有され
ていることを特徴とするものである。That is, the present invention provides an electrophotographic photoreceptor in which a photosensitive layer is provided on a conductive support, in which the photosensitive layer has the above general formula (I
) is characterized in that it contains an amino compound represented by the following as an active ingredient.
以下に本発明を添附の図面を参照しながらさらに詳細に
説明する。第１図ないし第３図は本発明に係る感光体の
代表的な三個の断面図であり、そこに付された番号で１
は導電性支持体、２．２’、２’は感光層、３は電荷発
生物質、４は電荷搬送媒体又は電荷搬送層、５は電荷発
生層を表わしている。The present invention will be explained in more detail below with reference to the accompanying drawings. 1 to 3 are three representative cross-sectional views of the photoreceptor according to the present invention, and the numbers assigned thereto are 1.
2.2', 2' are photosensitive layers; 3 is a charge generating substance; 4 is a charge transporting medium or layer; 5 is a charge generating layer.
本発明で用いられる前記一般式（１）で示されるアミノ
化合物は特開昭５７−７３０７６号、特開昭５７−１７
８７９９号、 特開昭５７−２０５４３７号、特開昭５
７−２０７２５２号、特開昭５８−２４６９６号および
特開昭５８−６９２０２号公報に記載のスチルベン化合
物を接触水素化することにより得られる。The amino compound represented by the general formula (1) used in the present invention is disclosed in JP-A-57-73076 and JP-A-57-17.
No. 8799, JP-A-57-205437, JP-A-Sho 5
It can be obtained by catalytic hydrogenation of the stilbene compounds described in JP-A No. 7-207252, JP-A-58-24696, and JP-A-58-69202.
こうして得られる一般式（１）で表わされるアミノ化合
物の具体例を以下に例示する。Specific examples of the amino compound represented by the general formula (1) thus obtained are illustrated below.
本発明感光体は、上記のようなアミノ化合物の１種又は
２種以上を感光層２（２′又は２＃に含有させたもので
あるが、これらアミノ化合物の応用の仕方によって第１
図、第２図あるいは第３図に示したごとくに用いること
ができる。The photoreceptor of the present invention contains one or more of the above-mentioned amino compounds in the photosensitive layer 2 (2' or 2#).
It can be used as shown in FIG. 2 or 3.
第１図における感光体は導電性支持体１上にアミノ化合
物、増感染料および結合剤（結着樹脂）よりなる感光層
２が設けられたものである。The photoreceptor shown in FIG. 1 has a photosensitive layer 2 comprising an amino compound, a sensitizing dye, and a binder (binder resin) on a conductive support 1. The photoreceptor shown in FIG.
ここでのアミノ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アミノ化合物
を介して行なわれる。しかしながら、アミノ化合物は光
の可視領域においてはほとんど吸収を有していないので
、可視光で画像を形成する目的のためには可視領域に吸
収を有する増感染料を添加して増感する必要がある。The amino compound here acts as a photoconductive substance, and the generation and transfer of charge carriers necessary for light attenuation take place via the amino compound. However, amino compounds have almost no absorption in the visible region of light, so in order to form images with visible light, it is necessary to sensitize them by adding a sensitizing dye that absorbs in the visible region. be.
第２図におれる感光体は、導電性支持体１上に電荷発生
層３をアミノ化合物と結合剤とからなる電荷搬送媒体４
の中に分散せしめた感光層２′が設けられたものである
。 ここでのアミノ化合物は結合剤（又は、結合剤及び
可塑剤）とともに電荷搬送媒体を形成し、一方、電荷発
生物質３（無機又は有機顔料のような電荷発生物質）が
電荷担体を発生する。この場合、電荷搬送媒体４は主と
して電荷発生物質３が発生する電荷担体を受入れ、これ
を搬送する作用を担肖している。そして、この感光体に
あっては電荷発生層とアミノ化合物とが、たがいに、主
として可視領域において吸収波長領域が重ならないとい
うのが基１本的条件である。これは、電荷発生物質３に
電荷担体を効率よく発生させるためには電荷発生物質表
面まで、光を透過させる必要があるからである。一般式
（Ｉ）で表わされるアミノ化合物は可視領域にほとんど
吸収がなく、一般に可視領域の光線を吸収し、電荷担体
を発生する電荷発生層３と組合わせた場合、特に有効に
電荷搬送物質として働くのがその特長である。The photoreceptor shown in FIG. 2 has a charge generation layer 3 on a conductive support 1 and a charge transport medium 4 made of an amino compound and a binder.
A photosensitive layer 2' is provided dispersed in the photosensitive layer 2'. The amino compound here together with the binder (or binder and plasticizer) forms the charge transport medium, while the charge generating substance 3 (charge generating substance such as an inorganic or organic pigment) generates the charge carriers. In this case, the charge transport medium 4 mainly has the function of receiving charge carriers generated by the charge generating substance 3 and transporting them. The basic condition for this photoreceptor is that the absorption wavelength regions of the charge generation layer and the amino compound do not overlap each other, mainly in the visible region. This is because in order to efficiently generate charge carriers in the charge generation material 3, it is necessary to transmit light to the surface of the charge generation material. The amino compound represented by the general formula (I) has almost no absorption in the visible region, and generally absorbs light in the visible region, and when combined with the charge generation layer 3 that generates charge carriers, it is particularly effective as a charge transport material. Its feature is that it works.
第３図における感光体は、導電性支持体１上に電荷発生
物質３を主体とする電荷発生層５と、アミノ化合物を含
有する電荷搬送層４との積層からなる感光層２′が設け
られたものである。In the photoreceptor shown in FIG. 3, a photosensitive layer 2' consisting of a laminated layer of a charge generation layer 5 mainly composed of a charge generation substance 3 and a charge transport layer 4 containing an amino compound is provided on a conductive support 1. It is something that
この感光体では、電荷搬送層４を透過した光が電荷発生
層５に到達し、その領域で電荷担体の発生が起こり、一
方、電荷搬送層４は電荷担体の注入を受け、その搬送を
行なうもので、光減衰に必要な電荷担体の発生は、電荷
発生物質３で行なわれ、また電荷担体の搬送は、電荷搬
送層４（主としてアミノ化合物が働く）で行なわれる。In this photoreceptor, light transmitted through the charge transport layer 4 reaches the charge generation layer 5, and charge carriers are generated in that region, while the charge transport layer 4 receives charge carriers and transports them. The charge carriers necessary for light attenuation are generated by the charge generation substance 3, and the charge carriers are transported by the charge transport layer 4 (in which an amino compound mainly acts).
こうした機構は第２図に示した感光体においてした説明
と同様である。This mechanism is similar to the explanation given for the photoreceptor shown in FIG.
実際に本発明感光体を作製するには、第１図に示した感
光体であれば、結合剤を溶かした溶液にアミノ化合物の
１種又は２種以上を溶解し、更にこれに増感染料を加え
た液をつくり、これを導電性支持体１上に塗布し乾燥し
て感光層２を形成すればよい。In order to actually produce the photoreceptor of the present invention, in the case of the photoreceptor shown in FIG. 1, one or more amino compounds are dissolved in a solution containing a binder, and then a sensitizing agent is added The photosensitive layer 2 may be formed by preparing a liquid containing the above ingredients, applying it onto the conductive support 1, and drying it.
感光層２の厚さは３〜５０μｍ、好ましくは５〜２０μ
ｍが適当である。感光層２に占めるアミノ化合物の量は
３０〜７０重量％、好ましくは約５０重量％であり、ま
た、感光層２に占める増感染料の量は０．１〜５重量％
、好ましくは０．５〜３重量％である。増感染料として
は、ブリリアントグリーン、ビクトリアブルーＢ、メチ
ルバイオレット、クリスタルバイオレット、アシッドバ
イオレット６Ｂのようなトリアリールメタン染料、ロー
ダミンＢ、ローダミン６Ｇ、ローダミンＧエキストラ、
エオシンＳ、エリトロシン、ローズベンガル、フルオレ
セインのようなキサンチン染料、メチレンブルーのよう
なチアジン染料、シアニンのようなシアニン染料、２，
６−ジフェニル−４−（Ｎ、Ｎ−ジメチルアミノフェニ
ル）チアピリリウムバークロレート、ベンゾピリリウム
塩（特公昭４８−２５６５８号公報に記載）などのピリ
リウム染料などが挙げられる。なお、これらの増感染料
は単独で用いられてもｈ種以上が併用されてもよい。The thickness of the photosensitive layer 2 is 3 to 50 μm, preferably 5 to 20 μm.
m is appropriate. The amount of the amino compound in the photosensitive layer 2 is 30 to 70% by weight, preferably about 50% by weight, and the amount of the sensitizing dye in the photosensitive layer 2 is 0.1 to 5% by weight.
, preferably 0.5 to 3% by weight. As sensitizers, triarylmethane dyes such as brilliant green, Victoria blue B, methyl violet, crystal violet, acid violet 6B, rhodamine B, rhodamine 6G, rhodamine G extra,
Xanthine dyes such as eosin S, erythrosin, rose bengal, fluorescein, thiazine dyes such as methylene blue, cyanine dyes such as cyanine, 2,
Examples include pyrylium dyes such as 6-diphenyl-4-(N,N-dimethylaminophenyl)thiapyrylium verchlorate and benzopyrylium salt (described in Japanese Patent Publication No. 48-25658). Incidentally, these sensitizing agents may be used alone or in combination of H types or more.
また、第２図に示した感光体を作製するには、１種又は
２種以上のアミノ化合物と結合剤とを溶解した溶液に電
荷発生物質３の微粒子を分散せしめ、これを導電性支持
体１上に塗布し乾燥して感光層２′を形成すればよい。Further, in order to produce the photoreceptor shown in FIG. 2, fine particles of the charge generating substance 3 are dispersed in a solution containing one or more kinds of amino compounds and a binder, and the fine particles are dispersed on a conductive support. 1 and dried to form a photosensitive layer 2'.
感光層２′の厚さは３〜５０μｍ、好ましくは５〜２０
μｍが適当である。感光層２′に占めるアミノ化合物の
量は１０〜９５重量部％であり、また、感光層２′に占
める電荷発生物質３の量は０．１〜５０重量％好ましく
は１〜２０重量％である。電荷発生物質３としては、例
えばセレン、セレン−テルル、硫化カドミウム、硫化カ
ドミウム−セレンα−シリコンなどの無機顔料、有機顔
料としては例えばシーアイピグメントブルー２５（カラ
ーインデックスＣｌ２１１８０）、シーアイピグメント
レッド４１（カラーインデックスＣｌ２１２００）、シ
ーアイアシッドレッド５２ （ＣＩ４５１００）、シー
アイベーシックレッド３ （（Ｊ４５２１０）、カルバ
−ゾル骨格を有するアゾ顔料（特開昭５３−９５０３３
号公報に記載）、 ジスチリルベンゼン骨格を有するア
ゾ顔料（特開昭５３−１３３４４５号公報に記載）、ト
リフェニルアミン骨格を有するアゾ顔料（特開昭５３−
１３２３４７号公報に記載）、ジベンゾチオフェン骨格
を有するアゾ顔料（特開昭５４−２１７２８号公報に記
載）、オキサジアゾール骨格を有するアゾ顔料（特開昭
５４−１２７４２号公報に記載）、フルオレノン骨格を
有するアゾ顔料（特開昭５４−２２８３４号公報に記載
）、 ビススチルベン骨格を有するアゾ顔料（特開昭５
４−１７７３３号公報に記載）、ジスチリルオキサジア
ゾール骨格を有するアゾ顔料（特開昭５４−２１２９号
公報に記載）、 ジスチリルカルバゾール骨格を有する
アゾ顔料（特開昭５４−１４９６７号公報に記載）など
のアゾ顔料、例えばシーアイピグメントブルー１６ （
ＣＩ７４１００）などのフタロシアニン系顔料、例えば
シーアイバットブラウン５ （ＣＩ７３４１０）、 シ
ーアイバットダイ（ＣＩ７３０３０）などのインジゴ系
顔料、アルゴスカーレットＢ（バイエル社製）、イシダ
ンスレンスカーレットＲ（バイエル社！ｉりなどのペリ
レン系顔料などが挙げられる。なお、これらの電荷発生
物質は単独で用いられても２種以上が併用されてもよい
。The thickness of the photosensitive layer 2' is 3 to 50 μm, preferably 5 to 20 μm.
μm is appropriate. The amount of the amino compound in the photosensitive layer 2' is 10 to 95 parts by weight, and the amount of the charge generating substance 3 in the photosensitive layer 2' is 0.1 to 50% by weight, preferably 1 to 20% by weight. be. Examples of the charge generating substance 3 include inorganic pigments such as selenium, selenium-tellurium, cadmium sulfide, cadmium sulfide-selenium α-silicon, and organic pigments such as C.I. Pigment Blue 25 (color index Cl21180) and C.I. Pigment Red 41 (color index Cl21200), C.I. Acid Red 52 (CI45100), C.I. Basic Red 3 ((J45210)), azo pigment having a carbazole skeleton (JP-A-53-95033)
Azo pigments having a distyrylbenzene skeleton (described in JP-A-53-133445), azo pigments having a triphenylamine skeleton (described in JP-A-53-133445),
132347), azo pigments having a dibenzothiophene skeleton (described in JP-A-54-21728), azo pigments having an oxadiazole skeleton (described in JP-A-54-12742), fluorenone skeletons (described in JP-A-54-22834), an azo pigment with a bisstilbene skeleton (described in JP-A-54-22834),
4-17733), azo pigments having a distyryloxadiazole skeleton (described in JP-A-54-2129), azo pigments having a distyrylcarbazole skeleton (described in JP-A-54-14967), azo pigments such as C.I. Pigment Blue 16 (
Phthalocyanine pigments such as CI74100), indigo pigments such as C.I. Butt Brown 5 (CI73410) and C.I. Butt Dye (CI73030), Argo Scarlet B (manufactured by Bayer AG), Isidane Stren Scarlet R (manufactured by Bayer AG), etc. These charge generating substances may be used alone or in combination of two or more types.
更に、第３図に示した感光体を作製するには、導電性支
持体１上に電荷発生物質を真空蒸着するか或いは、電荷
発生物質の微粒子３を必要によって結合剤を溶解した適
当に溶媒中に分散した分散液を塗布し乾燥するかして、
更に必要であればパフ研磨などの方法によって表面仕上
げ、膜厚調整などを行なって電荷発生層５を形成し、こ
の上に１種又は２種以上のアミノ化合物と結合剤とを溶
解した溶液を塗布し乾燥して電荷搬送層４を形成すれば
よい。なお、ここで電荷発生層５の形成に用いられる電
荷発生物質は前記の感光層２′の説明においてしたのと
同じものである。Furthermore, in order to produce the photoreceptor shown in FIG. 3, a charge-generating substance is vacuum-deposited on a conductive support 1, or fine particles 3 of a charge-generating substance are deposited in a suitable solvent in which a binder is dissolved if necessary. Apply the dispersion liquid dispersed inside and dry it,
Furthermore, if necessary, surface finishing and film thickness adjustment are performed by a method such as puff polishing to form a charge generation layer 5, and a solution containing one or more amino compounds and a binder is applied thereon. The charge transport layer 4 may be formed by coating and drying. The charge generating material used to form the charge generating layer 5 is the same as that used in the description of the photosensitive layer 2'.
電荷発生層５の厚さは５μｍ以下好ましくは２μｍ以下
であり、電荷搬送Ｎ４の厚さは３〜５０μｍ好ましくは
５〜２０μｍが適当である。電荷発生層５が電荷発生物
質の微粒子３を結合剤中に分散させたタイプのものにあ
っては、電荷発生物質の微粒子３の電荷発生Ｎｊ５に占
める割合は１０〜９５重量％、好ましくは５０〜９０重
量％程度である。また、電荷搬送層４に占めるアミノ化
合物の量は１０〜９５重量％、好ましくは３０〜９０重
量％である。The thickness of the charge generation layer 5 is 5 μm or less, preferably 2 μm or less, and the thickness of the charge transport layer N4 is suitably 3 to 50 μm, preferably 5 to 20 μm. When the charge generation layer 5 is of a type in which charge generation substance fine particles 3 are dispersed in a binder, the proportion of the charge generation substance fine particles 3 in the charge generation Nj5 is 10 to 95% by weight, preferably 50% by weight. It is about 90% by weight. Further, the amount of the amino compound in the charge transport layer 4 is 10 to 95% by weight, preferably 30 to 90% by weight.
なお、これらいずれの感光体製造においても導電性支持
体１としては、アルミニウムなどの金属板又は金属箔、
アルミニウムなどの金属を蒸着したプラスチックフィル
ム、あるいは、導電処理を施した紙などが用いられる。In any of these photoconductor productions, the conductive support 1 may be a metal plate or metal foil such as aluminum,
A plastic film coated with a metal such as aluminum, or paper treated with conductivity is used.
また、結合剤としては、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、ポリカーボネ
ートなどの縮合樹脂や、ポリビニルケトン、ポリスチレ
ン、ポリ−Ｎ−ビニルカルバゾール、ポリアクリルアミ
ドのようなビニル重合体などが用いられるが、絶縁性で
かつ接着性のある樹脂はすべて使用できる。必要により
可塑剤が結合剤に加えられてるが、そうした可塑剤とし
てはハロゲン化パラフィン、ポリ塩化ビフェニル、ジメ
チルナフタリン、ジブチルフタレートなどが例示できる
。As the binder, condensation resins such as polyamide, polyurethane, polyester, epoxy resin, polyketone, and polycarbonate, and vinyl polymers such as polyvinyl ketone, polystyrene, poly-N-vinylcarbazole, and polyacrylamide are used. , any insulating and adhesive resin can be used. If necessary, a plasticizer is added to the binder, and examples of such plasticizers include halogenated paraffins, polychlorinated biphenyls, dimethylnaphthalene, and dibutyl phthalate.
更に、以上のようにして得られる感光体には、導電性支
持体と感光層の間に、必要に応じて接着層又はバリヤ層
を設けることができる。これらの層に用いられる材料と
しては、ポリアミド。Furthermore, in the photoreceptor obtained as described above, an adhesive layer or a barrier layer can be provided between the conductive support and the photosensitive layer, if necessary. The material used for these layers is polyamide.
ニトロセルロース、酸化アルミニウムなどであり、また
膜厚は１μｍ以下が好ましい。Nitrocellulose, aluminum oxide, etc. are used, and the film thickness is preferably 1 μm or less.
本発明の感光体を用いて複写を行なうには、感光面に帯
電、露光を施した後、現像を行ない、必要によって、紙
などへ転写を行なう１本発明の感光体は感度が高く、ま
た可撓性に富むなどの優れた利点を有している。To make a copy using the photoreceptor of the present invention, the photoreceptor surface is charged, exposed, developed, and if necessary, transferred to paper or the like.The photoreceptor of the present invention has high sensitivity, and It has excellent advantages such as high flexibility.
以下に実施例を示す、下記実施例において部はすべて重
量部である。Examples are shown below, in which all parts are by weight.
製造例
４−Ｎ、Ｎ−ジフェニルアミノスチルベン１０．４２ｇ
をジオキサン１００ｍ ｆｔに溶かし、これに５％パラ
ジウム−炭素１．０４ ｇを加え、２５℃水素圧１気圧
で振どう大水素化装置で水素化した。水素化終了後セラ
イトと共にろ過し、ジオキサンを減圧上留去し、無色油
状物を得た。これをシリカゲル−トルエンでカラムクロ
マト処理し。Production Example 4-N,N-diphenylaminostilbene 10.42g
was dissolved in 100 m ft of dioxane, 1.04 g of 5% palladium-carbon was added thereto, and the mixture was hydrogenated at 25° C. and a hydrogen pressure of 1 atm in a large-scale hydrogenation apparatus under shaking. After the hydrogenation was completed, the mixture was filtered with Celite, and dioxane was distilled off under reduced pressure to obtain a colorless oil. This was subjected to column chromatography using silica gel and toluene.
無色語調液体の
４−フェネチルトリフェニルアミン
（化合物Ｎα６） ９．０３ｇ （収率８６％）を得た
。9.03 g (yield: 86%) of 4-phenethyltriphenylamine (compound Nα6) as a colorless liquid was obtained.
元素分析値（％）
ＨＮ
実測値 ８９．２７ ６．６１ ４．０２赤外吸収スペ
クトル（ＫＢｒ錠剤法）では９６５ａ＋１−１のトラン
スオレフィンのＣ−Ｈ面外変角振動に基づく吸収の消失
が認められた。Elemental analysis value (%) HN Actual value 89.27 6.61 4.02 In the infrared absorption spectrum (KBr tablet method), disappearance of absorption based on C-H out-of-plane bending vibration of 965a+1-1 transolefin was observed. It was done.
実施例１
電荷発生物質としてダイアンブルー（シーアイピグメン
トブルー２５、Ｃｌ２１１８０）７６部、ポリエステル
樹脂（バイロン２００．ｔｅｌ東洋紡績製）の２％テト
ラヒドロフラン溶液１２６０部およびテトラヒドロフラ
ン３７００部をボールミル中で粉砕混合し、得られた分
散液をアルミニウム蒸着したポリエステルベースよりな
る導電性支持体のアルミニウム面上にドクターブレード
を用いて塗布し、自然乾燥して厚さ約１μｍの電荷発生
層を形成した。Example 1 76 parts of Diane Blue (CI Pigment Blue 25, Cl21180) as a charge generating substance, 1260 parts of a 2% tetrahydrofuran solution of polyester resin (Vylon 200.tel manufactured by Toyobo Co., Ltd.) and 3700 parts of tetrahydrofuran were ground and mixed in a ball mill. The resulting dispersion was applied using a doctor blade onto the aluminum surface of a conductive support made of a polyester base coated with aluminum vapor, and air-dried to form a charge generation layer with a thickness of about 1 μm.
一方、電荷搬送物質としてＮα７のアミノ化合物２部、
ポリカーボネート樹脂（パンライトに１３００、■帝人
製）２部およびテトラヒドロフラン１６部を混合溶解し
て溶液とした後、これを前記電荷発生層上にドクターブ
レードを用いて塗布し、８０℃で２分間、ついで１０５
℃で５分間乾燥して厚さ約２０μｍの電荷搬送層を形成
せしめて感光体Ｎα１を作成した。On the other hand, 2 parts of an amino compound of Nα7 as a charge transport substance,
After mixing and dissolving 2 parts of polycarbonate resin (Panlite 1300, manufactured by Teijin) and 16 parts of tetrahydrofuran to form a solution, this was applied onto the charge generation layer using a doctor blade and heated at 80°C for 2 minutes. Then 105
A charge transport layer having a thickness of about 20 μm was formed by drying at ℃ for 5 minutes to prepare a photoreceptor Nα1.
実施例２〜２７
電荷発生物質および電荷搬送物質（アミノ化合物）を表
−１に示したものに代えた以外は実施例１とまったく同
様にして感光体＆２〜２７を作成した。Examples 2 to 27 Photoreceptors &2 to 27 were prepared in exactly the same manner as in Example 1, except that the charge generating substance and the charge transport substance (amino compound) were replaced with those shown in Table 1.
（以下余白）
表−１
実施例２８
厚さ約３００μｍのアルミニウム板上に、セレンを厚さ
約１μｍに真空蒸着して電荷発生層を形成せしめた。次
いでＮα７のアミノ化合物２部、ポリエステル樹脂（デ
ュポン社製ポリエステルアドヒーシブ４９０００） ３
部およびテトラヒドロフラン４５部を混合、溶解して電
荷搬送層形成液をつくり、これを上記の電荷発生層（セ
レン蒸着層）上にドクターブレードを用いて塗布し、自
然乾燥した後、減圧下で乾燥して厚さ約１０μｍの電荷
搬送層を形成せしめて、本発明の感光体Ｎα２８を得た
。(Margin below) Table 1 Example 28 A charge generation layer was formed by vacuum evaporating selenium to a thickness of about 1 μm on an aluminum plate having a thickness of about 300 μm. Next, 2 parts of an amino compound of Nα7, 3 parts of polyester resin (Polyester Adhesive 49000 manufactured by DuPont)
A charge transport layer forming liquid was prepared by mixing and dissolving 1 part and 45 parts of tetrahydrofuran, and this was applied onto the above charge generation layer (selenium vapor deposited layer) using a doctor blade, air dried, and then dried under reduced pressure. A charge transport layer having a thickness of about 10 μm was formed in this manner to obtain a photoreceptor Nα28 of the present invention.
実施例２９
セレンの代りにペリレン系顔料
を用いて電荷発生層（但し、厚さは約０．３μｍ）を形
成し、またアミノ化合物をＮα７の代りにＮｎ’ ６の
ものを用いた以外は実施例２８とまったく同様にして感
光体Ｎα２９を作成した。Example 29 The same procedure was carried out except that a perylene pigment was used instead of selenium to form the charge generation layer (however, the thickness was about 0.3 μm), and an amino compound of Nn'6 was used instead of Nα7. A photoreceptor Nα29 was prepared in exactly the same manner as in Example 28.
実施例３０
ダイアンブルー（実施例１で用いたものと同じ）１部に
テトラヒドロフラン１５８部を加えた混合物をボールミ
ル中で粉砕、混合した後、これにＮα７のアミノ化合物
１２部、ポリエステル樹脂（デュポン社製ポリエステル
アドヒーシブ４９０００）１８部を加えて、さらに混合
して得た感光層形成液を、アルミニウム蒸着ポリエステ
ルフィルム上にドクターブレードを用いて塗布し、１０
０℃で３０分間乾燥して厚さ約１６μｍの感光層を形成
せしめて、本発明の感光体＆３０を作成した。Example 30 A mixture of 1 part of Diane Blue (same as that used in Example 1) and 158 parts of tetrahydrofuran was ground and mixed in a ball mill, and then mixed with 12 parts of an amino compound of Nα7 and a polyester resin (Dupont Co., Ltd.). The photosensitive layer forming liquid obtained by adding 18 parts of Polyester Adhesive 49000) and further mixing was applied onto an aluminum vapor-deposited polyester film using a doctor blade.
A photoreceptor &30 of the present invention was prepared by drying at 0° C. for 30 minutes to form a photosensitive layer with a thickness of about 16 μm.
かくしてつくられた感光体＆１〜３０について、市販の
静電複写紙試験装置（ＫＫ川用電機製作所製ＳＰ４２ｇ
型）を用いて−６に■又は＋６ＫＶ（７１：１０す放電
を２０秒間行なって帯電せしめた後、２０秒間暗所に放
置し、その時の表面電位Ｖｐｏ（ボルト）を測定し、つ
いでタングステンランプ光を、感光体表面の照度が２０
ルツクスになるよう照射してその表面電位がＶＰＯの１
７２になる迄の時間（秒）を求め、露光量Ｅ １／２（
ルックシス・秒）を算出した。その結果を表−２に示す
。The photoreceptors &1 to 30 thus produced were tested using a commercially available electrostatic copying paper tester (SP42g manufactured by KK Kawayo Denki Seisakusho).
After charging by performing a -6 or +6 KV (71:10) discharge for 20 seconds using a tungsten lamp, leave it in a dark place for 20 seconds, measure the surface potential Vpo (volt) at that time, and then use a tungsten lamp. The illuminance of the light on the surface of the photoreceptor is 20
lux so that the surface potential is 1 of VPO.
Find the time (seconds) it takes to reach 72, and calculate the exposure amount E 1/2 (
luxis seconds) was calculated. The results are shown in Table-2.
また、以上の各感光体を市販の電子写真複写機を用いて
帯電せしめた後、原図を介して光照射を行なって静電潜
像を形成せしめ、乾式現像剤を用いて現像し、得られた
画像（トナー画像）を普通紙上に静電転写し、定着した
ところ、鮮明な転写画像が得られた。現像剤として湿式
現像剤を用いた場合も同様に鮮明な転写画像が得られた
。In addition, after each of the photoreceptors described above is charged using a commercially available electrophotographic copying machine, light is irradiated through the original image to form an electrostatic latent image, and the image is developed using a dry developer. When the image (toner image) was electrostatically transferred onto plain paper and fixed, a clear transferred image was obtained. A similarly clear transferred image was obtained when a wet developer was used as the developer.
表−２
以上の実施例かられかるように、本発明の感光体は感光
特性に優れていることは勿論のこと、熱や機械的の衝撃
に対する強度が大で、しかも安価に製造することができ
る。Table 2 As can be seen from the examples above, the photoreceptor of the present invention not only has excellent photosensitive characteristics, but also has high strength against thermal and mechanical shocks, and can be manufactured at low cost. can.
第１図、第２図および第３図は本発明にかかわる電子写
真感光体の厚さ方向に拡大した断面図である。
１・・・導電性支持体
２．２’、２’・・・感光層
３・・・電荷発生物質
４・・・電荷搬送媒体又は電荷搬送層
５・・・電荷発生層
崩１図
飛２図
篤３図
昭和６２年特許願第１２９６７号
２、発明の名称
電子写真用感光体
３、 補正をする者
事件との関係 特許出願人
東京都大田区中馬込１丁目３番６号
（６７４）株式会社リ コ −
代表者 浜 １） 広
４、代現人
東京都千代田区麹町４丁目５番地（〒１０２）５、補正
の対象
補正の内容
明細書第１１〜１２頁のアミノ化合物Ｎα６６〜７７し
こ」
に訂正する。
以上1, 2, and 3 are cross-sectional views enlarged in the thickness direction of an electrophotographic photoreceptor according to the present invention. 1... Conductive support 2. 2', 2'... Photosensitive layer 3... Charge generating substance 4... Charge transporting medium or charge transporting layer 5... Charge generating layer breakdown 1 Figure 2 Figure Atsushi 3, 1986 Patent Application No. 12967 2, Name of the invention: Electrophotographic photoreceptor 3, Relationship with the person making the amendment: Patent applicant: 1-3-6 Nakamagome, Ota-ku, Tokyo (674) Ricoh Co., Ltd. - Representative Hama 1) Hiro 4, Daigenjin 4-5 Kojimachi, Chiyoda-ku, Tokyo (102) 5 Amino compound Nα66-77 on pages 11-12 of the statement of contents of the amendment that is the subject of the amendment "Shiko" is corrected. that's all
Claims (1)
アミノ化合物 ▲数式、化学式、表等があります▼（ I ） （式中Ｒ＾１は水素原子、アルキル基、アルコキシ基、
アリールオキシ基またはハロゲン原子を、Ｒ＾２水素原
子、置換アルキル基を含むアルキル基または置換もしく
は無置換のフェニル基を、Ｒ＾３及びＲ＾４はアルキル
基、アラルキル基またはアリール基を表わし、Ａｒは芳
香族炭化水素を表わす。） の少くとも１つを有効成分として含有する感光層を有す
ることを特徴とする電子写真用感光体。[Claims] 1. An amino compound represented by the following general formula (I) on a conductive support ▲ There are numerical formulas, chemical formulas, tables, etc. ▼ (I) (wherein R^1 is a hydrogen atom, an alkyl group , alkoxy group,
an aryloxy group or a halogen atom; R^2 represents a hydrogen atom, an alkyl group including a substituted alkyl group, or a substituted or unsubstituted phenyl group; R^3 and R^4 represent an alkyl group, an aralkyl group, or an aryl group; Ar represents an aromatic hydrocarbon. 1.) An electrophotographic photoreceptor comprising a photosensitive layer containing at least one of the following as an active ingredient.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62012967A JPH0833663B2 (en) | 1987-01-21 | 1987-01-21 | Electrophotographic photoreceptor |
| US07/259,555 US4931350A (en) | 1987-01-20 | 1988-10-18 | Electrophotographic photoconductor having an arylalkylenearylamino photoconductor |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62012967A JPH0833663B2 (en) | 1987-01-21 | 1987-01-21 | Electrophotographic photoreceptor |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63180954A true JPS63180954A (en) | 1988-07-26 |
| JPH0833663B2 JPH0833663B2 (en) | 1996-03-29 |
Family
ID=11820012
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62012967A Expired - Lifetime JPH0833663B2 (en) | 1987-01-20 | 1987-01-21 | Electrophotographic photoreceptor |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0833663B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5102759A (en) * | 1989-12-01 | 1992-04-07 | Mitsubishi Kasei Corporation | Electrophotographic photoreceptor |
| US5298661A (en) * | 1988-10-20 | 1994-03-29 | Ricoh Company, Ltd. | Charge transporting materials and electrophotographic photoconductors using the same |
-
1987
- 1987-01-21 JP JP62012967A patent/JPH0833663B2/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5298661A (en) * | 1988-10-20 | 1994-03-29 | Ricoh Company, Ltd. | Charge transporting materials and electrophotographic photoconductors using the same |
| US5102759A (en) * | 1989-12-01 | 1992-04-07 | Mitsubishi Kasei Corporation | Electrophotographic photoreceptor |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0833663B2 (en) | 1996-03-29 |
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| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |