JPH04133064A - Electrophotographic sensitive body - Google Patents
Electrophotographic sensitive bodyInfo
- Publication number
- JPH04133064A JPH04133064A JP25590690A JP25590690A JPH04133064A JP H04133064 A JPH04133064 A JP H04133064A JP 25590690 A JP25590690 A JP 25590690A JP 25590690 A JP25590690 A JP 25590690A JP H04133064 A JPH04133064 A JP H04133064A
- Authority
- JP
- Japan
- Prior art keywords
- group
- charge
- layer
- photoreceptor
- aminopyrene
- 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
- -1 aminopyrene compound Chemical class 0.000 claims description 58
- 108091008695 photoreceptors Proteins 0.000 claims description 55
- 239000000126 substance Substances 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 239000004480 active ingredient Substances 0.000 claims description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract description 18
- 239000000463 material Substances 0.000 abstract description 17
- 239000002800 charge carrier Substances 0.000 abstract description 12
- 229910052782 aluminium Inorganic materials 0.000 abstract description 8
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract description 8
- RMMXTBMQSGEXHJ-UHFFFAOYSA-N Aminophenazone Chemical compound O=C1C(N(C)C)=C(C)N(C)N1C1=CC=CC=C1 RMMXTBMQSGEXHJ-UHFFFAOYSA-N 0.000 abstract description 4
- 239000006185 dispersion Substances 0.000 abstract description 4
- 239000000203 mixture Substances 0.000 abstract description 4
- 238000002156 mixing Methods 0.000 abstract description 3
- 229920001225 polyester resin Polymers 0.000 abstract description 3
- 239000004645 polyester resin Substances 0.000 abstract description 3
- 229920005668 polycarbonate resin Polymers 0.000 abstract description 2
- 239000004431 polycarbonate resin Substances 0.000 abstract description 2
- 238000002513 implantation Methods 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 59
- 230000032258 transport Effects 0.000 description 24
- 239000011230 binding agent Substances 0.000 description 17
- 239000000049 pigment Substances 0.000 description 16
- 239000000975 dye Substances 0.000 description 10
- 229920005989 resin Polymers 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 7
- 239000010419 fine particle Substances 0.000 description 7
- 230000001235 sensitizing effect Effects 0.000 description 7
- YZVWKHVRBDQPMQ-UHFFFAOYSA-N 1-aminopyrene Chemical class C1=C2C(N)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 YZVWKHVRBDQPMQ-UHFFFAOYSA-N 0.000 description 6
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 6
- 229910052711 selenium Inorganic materials 0.000 description 6
- 239000011669 selenium Substances 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 3
- WUPHOULIZUERAE-UHFFFAOYSA-N 3-(oxolan-2-yl)propanoic acid Chemical compound OC(=O)CCC1CCCO1 WUPHOULIZUERAE-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 229910052980 cadmium sulfide Inorganic materials 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 239000012860 organic pigment Substances 0.000 description 3
- 239000004014 plasticizer Substances 0.000 description 3
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 3
- 239000011241 protective layer Substances 0.000 description 3
- 125000001424 substituent group Chemical group 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
- QNLZIZAQLLYXTC-UHFFFAOYSA-N 1,2-dimethylnaphthalene Chemical compound C1=CC=CC2=C(C)C(C)=CC=C21 QNLZIZAQLLYXTC-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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-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
- 150000001412 amines Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 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
- 230000005496 eutectics Effects 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 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
- 229920002647 polyamide Polymers 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 229920006267 polyester film Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical class C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 230000035939 shock Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000006163 transport media 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
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- 125000005978 1-naphthyloxy group Chemical group 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000005979 2-naphthyloxy group Chemical group 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 description 1
- RHPVVNRNAHRJOQ-UHFFFAOYSA-N 4-methyl-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1NC1=CC=C(C)C=C1 RHPVVNRNAHRJOQ-UHFFFAOYSA-N 0.000 description 1
- 125000006189 4-phenyl benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- ODPXEURIXUYULR-UHFFFAOYSA-N 7-tert-butyl-1-iodopyrene Chemical compound C1=CC(I)=C2C=CC3=CC(C(C)(C)C)=CC4=CC=C1C2=C43 ODPXEURIXUYULR-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- 239000004419 Panlite Substances 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 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
- JYDZYJYYCYREGF-UHFFFAOYSA-N [Cd].[Se]=S Chemical compound [Cd].[Se]=S JYDZYJYYCYREGF-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 125000005530 alkylenedioxy group Chemical group 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
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 125000003828 azulenyl group Chemical group 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
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 125000006267 biphenyl group Chemical group 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
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 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
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 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
- 108010011222 cyclo(Arg-Pro) Proteins 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 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
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004119 disulfanediyl group Chemical group *SS* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000003480 eluent Substances 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
- 150000002148 esters Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 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
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 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
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052740 iodine Chemical group 0.000 description 1
- 239000011630 iodine Chemical group 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 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 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 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
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 229960000907 methylthioninium chloride Drugs 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical class C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 239000003921 oil Substances 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
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 229920003023 plastic Polymers 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
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 150000003071 polychlorinated biphenyls Chemical class 0.000 description 1
- 229920000647 polyepoxide 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
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 125000001725 pyrenyl group Chemical group 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
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 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
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000001016 thiazine dye Substances 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000001003 triarylmethane dye Substances 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000006617 triphenylamine group Chemical group 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 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
- 238000007738 vacuum evaporation Methods 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229940075420 xanthine Drugs 0.000 description 1
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
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 [Industrial Field of Application] The present invention relates to an electrophotographic photoreceptor, and more particularly to an electrophotographic photoreceptor containing a specific compound in its photosensitive layer.
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。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. Obtain an electrostatic latent image.
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。One of the image forming methods in which this latent image area is developed and visualized with 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. It is.
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）１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 one 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
実状である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、！２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。By the way, the reality is 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). The conditions for this are fully satisfied, but the manufacturing conditions are difficult. It also has drawbacks such as high manufacturing cost, lack of flexibility, difficulty in processing into a belt shape, and sensitivity to heat and mechanical shock, which requires careful handling.
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。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。例えば、ポリ−Ｎ−ビニル
カルバゾールと２．４．７〜トリニトロフルオレン−９
−オンとからなる感光体（米国特許第３４８４２３７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４８−２
５６５８号公報に記載）、有機顔料を主成分とする感光
体（特開昭４７−３７５４３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４
７−１０７３５号公報に記載）、トリフェニルアミン化
合物を色素増感してなる感光体（米国特許第３，１８０
，７３０号）、アミン誘導体を電荷輸送材料として用い
る感光体（特開昭５７−１９５２５４号公報）、ポリ−
Ｎ−ビニルカルバゾールとアミン誘導体を電荷輸送材料
として用いる感光体（特開昭５８−１１５５号公報）、
多官能第３アミン化合物なかでもベンジジン化合物を光
導電材料として用いる感光体（米国特許第３，２６５，
４９６号、特公昭３９−１１５４６号公報、特開昭５３
−２７０３３号公報）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。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. For example, poly-N-vinylcarbazole and 2.4.7-trinitrofluorene-9
-on (described in U.S. Pat. No. 3,484,237), a photoreceptor made by sensitizing poly-N-vinylcarbazole with a pyrylium salt dye (Japanese Patent Publication No. 48-2
5658), a photoreceptor whose main component is an organic pigment (described in JP-A-47-37543), a photoreceptor whose main component is a eutectic complex consisting of a dye and a resin (JP-A-47-37543), a photoreceptor whose main component is a eutectic complex consisting of a dye and a resin
No. 7-10735), a photoreceptor made by dye-sensitizing a triphenylamine compound (U.S. Pat. No. 3,180)
, No. 730), photoreceptors using amine derivatives as charge transport materials (Japanese Unexamined Patent Publication No. 195254/1983), poly-
A photoreceptor using N-vinylcarbazole and an amine derivative as a charge transport material (Japanese Patent Application Laid-Open No. 1155/1983),
A photoreceptor using a benzidine compound among polyfunctional tertiary amine compounds as a photoconductive material (U.S. Pat. No. 3,265,
No. 496, Japanese Patent Publication No. 39-11546, Japanese Unexamined Patent Publication No. 53
-27033). Although these photoreceptors have excellent properties and are considered to be of high practical value, considering the various requirements for photoreceptors in electrophotography, it is still difficult to fully meet these requirements. The reality is that we have not been able to obtain anything that satisfies us.
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
分満足しろる感光体を提供することにある。更に、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 An object of the present invention is to eliminate the various drawbacks of the conventional photoreceptors mentioned above and to provide a photoreceptor that fully satisfies 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.
本発明によれば、導電性支持体上に下記一般式（Ｉ）で
表わされるアミノピレン化合物の少なくとも１種を有効
成分として含有することを特徴とする電子写真用感光体
が提供される。According to the present invention, there is provided an electrophotographic photoreceptor characterized in that it contains at least one aminopyrene compound represented by the following general formula (I) as an active ingredient on a conductive support.
Ｈ，Ｃ′”ＣＨ。H,C′”CH.
（式中、Ｘは臭素もしくはヨウ素を表わす。）で表わさ
れるハロゲノピレン化合物と、一般式％式％
［）
（Ｒ１，Ｒ２は前記と同じ）
で表わされるアミン化合物とを反応させるかもしくは下
記式（ＩＶ）
（式中、Ｒ１，Ｒ”は置換もしくは無置換のアルキル基
又は置換もしくは無置換のアリール基を表わす、）
本発明において感光層に含有させる前記一般式（Ｉ）で
表わされるアミノピレン化合物は、例えば一般式（ｎ）
で表わされる１−アミノ−？−ｔｅｒｔ−ブチルピレン
と、一般式（Ｖ）
Ｘ−Ｒ１（ｏｒ Ｘ−Ｒ”） （Ｖ）（
Ｒ１，Ｒ”及びＸは前記と同じ）
で表わされるハロゲン化物とを反応させることにより製
造される。(wherein, X represents bromine or iodine) is reacted with an amine compound represented by the general formula % [) (R1 and R2 are the same as above) or the following formula ( IV) (In the formula, R1 and R'' represent a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.) In the present invention, the aminopyrene compound represented by the general formula (I) to be contained in the photosensitive layer is , for example, 1-amino-?-tert-butylpyrene represented by general formula (n) and general formula (V)
R1, R'' and X are the same as above).
前記−形成（１）において、Ｒ１及びＲ２がアリール基
の場合かかる具体例としてはフェニル基、ビフェニル基
、ターフェニル基等の非縮合炭素環式の芳香族基及び縮
合多環式炭化水素基もしくは複素環式芳香族炭化水素基
が挙げられる。In the above-mentioned -formation (1), when R1 and R2 are aryl groups, specific examples thereof include non-fused carbocyclic aromatic groups such as phenyl group, biphenyl group, terphenyl group, and fused polycyclic hydrocarbon groups; Examples include heterocyclic aromatic hydrocarbon groups.
この場合、縮合多環式炭化水素基としては、好ましくは
環を形成する炭素数が１８個以下のもの例えば、ペンタ
レニル基、インデニル基、ナフチル基、アズレニル基、
ヘプタレニル基、ビフェニリル基、ａｔ−インデニル基
、フルオレニル基、Ｓ−インダセニル基、アセナフチレ
ニル基、プレイアデニル基、アセナフチニル基、ツェナ
レニル基、フェナントリル基、アントリル基、フルオラ
ンテニル基、アセフェナントリレニル基、アセアントリ
レニル基、トリフェニレニル基、ピレニル基、クリセニ
ル基、及びナツタセニル基等が挙げられる。In this case, the fused polycyclic hydrocarbon group preferably has 18 or less carbon atoms forming a ring, such as a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group,
heptarenyl group, biphenylyl group, at-indenyl group, fluorenyl group, S-indacenyl group, acenaphthylenyl group, plaiadenyl group, acenaphthynyl group, zenarenyl group, phenanthryl group, anthryl group, fluoranthenyl group, acephenanthrylenyl group, Examples include aceantrylenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, and natutasenyl group.
複素環式炭化水素基としては、チエニル、フリル、２−
ピリジル、４−ピリジル、３−インドリル、２−キツリ
ニル、３，４−ベンズピラニル、アクリジニル、チアゾ
リル、ベンゾチアゾロニル、９−メチルカルバゾリル、
９−エチルカルバゾリル、９−プロピルカルバゾリル、
９−フェニルカルバゾリル、９−トリルカルバゾリル、
４−ピラゾリルの多基が挙げられる、また、アリール基
は以下に示すような置換基を有するものも含まれる。Examples of the heterocyclic hydrocarbon group include thienyl, furyl, 2-
Pyridyl, 4-pyridyl, 3-indolyl, 2-chyturinyl, 3,4-benzpyranyl, acridinyl, thiazolyl, benzothiazolonyl, 9-methylcarbazolyl,
9-ethylcarbazolyl, 9-propylcarbazolyl,
9-phenylcarbazolyl, 9-tolylcarbazolyl,
Examples include 4-pyrazolyl groups, and aryl groups include those having substituents as shown below.
（１）ハロゲン原子、シアノ基、ニトロ基（２）アルキ
ル基、好ましくは、Ｃ２〜Ｃ１□とりわけ０１〜Ｃｓ、
さらに好ましくはＣ工〜Ｃ４の直鎖または分岐鎖のアル
キル基であり、これらのアルキル基はさらにフッ素子、
水酸基、シアノ基、Ｃ工〜Ｃ９のアルコキシ基、フェニ
ル基又はハロゲン原子、Ｃ工〜０４のアルキル基もしく
はＣ□〜Ｃ４のアルコキシ基で、置換されたフェニル基
を含有してもよい。具体的には、メチル基、エチル基、
ｎ−プロピル基、ｊ−プロピル基、ｔ−ブチル基、Ｓ−
ブチル基、ｎ−ブチル基、ｉ−ブチル基、トリフルオロ
メチル基、２−ヒドロキシエチル基、２−シアノエチル
基、２−ニドキシエチル基、２−メトキシエチル基、ベ
ンジル基、４−クロロベンジル基、４−メチルベンジル
基、４−メトキシベンジル基、４−フェニルベンジル基
等が挙げられる。(1) halogen atom, cyano group, nitro group (2) alkyl group, preferably C2-C1□especially 01-Cs,
More preferred are C-C4 linear or branched alkyl groups, and these alkyl groups further include a fluorine element,
It may contain a phenyl group substituted with a hydroxyl group, a cyano group, a C-C9 alkoxy group, a phenyl group or a halogen atom, a C-04 alkyl group, or a C□-C4 alkoxy group. Specifically, methyl group, ethyl group,
n-propyl group, j-propyl group, t-butyl group, S-
Butyl group, n-butyl group, i-butyl group, trifluoromethyl group, 2-hydroxyethyl group, 2-cyanoethyl group, 2-nidoxyethyl group, 2-methoxyethyl group, benzyl group, 4-chlorobenzyl group, 4 -methylbenzyl group, 4-methoxybenzyl group, 4-phenylbenzyl group, etc.
（３）アルコキシ基（−〇Ｒよ）；Ｒ１は（２）で定義
したアルキル基を表わす、具体的には、メトキシ基、エ
トキシ基、ｎ−プロポキシ基、ｉ−プロポキシ基、ｔ−
ブトキシ基、ｎ−ブトキシ基、Ｓ−ブトキシ基、ｉ−ブ
トキシ基、２−ヒドロキシエトキシ基、２−シアノエト
キシ基、ベンジルオキシ基、４−メチルベンジルオキシ
基、トリフルオロメトキシ基等が挙げられる。(3) Alkoxy group (-○R); R1 represents the alkyl group defined in (2), specifically, methoxy group, ethoxy group, n-propoxy group, i-propoxy group, t-
Examples include butoxy group, n-butoxy group, S-butoxy group, i-butoxy group, 2-hydroxyethoxy group, 2-cyanoethoxy group, benzyloxy group, 4-methylbenzyloxy group, trifluoromethoxy group, and the like.
（４）アリールオキシ基ニアリール基としてフェニル基
、ナフチル基があげられる。これは、Ｃ工〜Ｃ４のアル
コキシ基、０１〜０４のアルキル基またはハロゲン原子
を置換基として含有してもよい。具体的には、フェノキ
シ基、１−ナフチルオキシ基、２−ナフチルオキシ基、
４−メチルフェノキシ基、４−メトキシフェノキノ基、
４−クロロフェノキシ基、６−メチル−２−ナフチルオ
キシ基等が挙げられる。(4) Aryloxy group Niaryl groups include phenyl and naphthyl groups. This may contain a C-C4 alkoxy group, a 01-04 alkyl group, or a halogen atom as a substituent. Specifically, phenoxy group, 1-naphthyloxy group, 2-naphthyloxy group,
4-methylphenoxy group, 4-methoxyphenoquino group,
Examples include 4-chlorophenoxy group and 6-methyl-2-naphthyloxy group.
（５）アルキルメルカプト基（−３Ｒ□）；Ｒ工は（２
）で定義したアルキル基を表わす、具体的にはメチルチ
オ基、エチルチオ基、フェニルチオ基、ｐ−メチルフェ
ニルチオ基等が挙げられる。(5) Alkylmercapto group (-3R□); R is (2
), specific examples include a methylthio group, an ethylthio group, a phenylthio group, and a p-methylphenylthio group.
子、（２）で定義したアルキル基、又はアリール基を表
わし、アリール基としては２例えばフェニル基、ビフェ
ニリル基又はナフチル基が挙げられ、これらはＣ□−０
４のアルコキシ基、０１−０４のアルキル基、又はハロ
ゲン原子を置換基として含有してもよい。Ｒ２とＲ□は
共同で環を形成しても良い。またアリール基上の炭素原
子と共同で環を形成してもよい。）
具体的には、アミノ基、ジエチルアミノ基、Ｎ−メチル
ーＮ−フェニルアミノ基、Ｎ、Ｎ−ジフェニルアミノ基
、Ｎ、Ｎ−ジ（Ｐ−トリール）アミノ基、ジベンジルア
ミノ基、ピペリジノ基、モルホリノ基、ユロリジル基等
が挙げられる。represents an alkyl group or an aryl group as defined in (2), and examples of the aryl group include a phenyl group, a biphenylyl group, or a naphthyl group, and these are C□-0
It may contain an alkoxy group of 4, an alkyl group of 01-04, or a halogen atom as a substituent. R2 and R□ may jointly form a ring. Further, a ring may be formed in collaboration with the carbon atom on the aryl group. ) Specifically, amino group, diethylamino group, N-methyl-N-phenylamino group, N,N-diphenylamino group, N,N-di(P-tolyl)amino group, dibenzylamino group, piperidino group, Examples include morpholino group and urolidyl group.
（７）メチレンジオキシ基、又はメチレンジチオ基等の
アルキレンジオキシ基又はアルキレンジチオ基、等が挙
げられる。(7) Examples include methylene dioxy groups, alkylene dioxy groups such as methylene dithio groups, and alkylene dithio groups.
また、一般式（Ｉ）において、Ｒ１およびＲ２がアルキ
ル基の場合、かかる具体例としては、アリール基で説明
した（２）アルキル基の具体例と同じである。Further, in the general formula (I), when R1 and R2 are alkyl groups, specific examples thereof are the same as (2) specific examples of alkyl groups explained for aryl groups.
以下、一般式（Ｉ）で表わされるアミノピレン化合物の
代表例を示す。Representative examples of the aminopyrene compound represented by the general formula (I) are shown below.
Ｒ” Ｒ”
＼ ／
Ｈ３Ｃ／
＼ＣＨ３
本発明の感光体は、上記のようなアミノピレン０化合物
の１種又は２種以上を感光Ｍ２（２′、２″、２″又は
２１／Ｌｌ）に含有させたものであるが、これらアミノ
ピレン化合物の応用の仕方によって第１図、第２図、第
３図、第４図あるいは第５図に示したごとくに用いるこ
とができる。R"R" \ / H3C / \CH3 The photoreceptor of the present invention contains one or more of the above-mentioned aminopyrene 0 compounds in the photoreceptor M2 (2', 2'', 2'' or 21/Ll). However, depending on the application of these aminopyrene compounds, they can be used as shown in FIG. 1, FIG. 2, FIG. 3, FIG. 4, or FIG. 5.
第１図における感光体は導電性支持体１上にアミノピレ
ン化合物、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。ここでのアミノピレ
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アミノピレン化合物を介し
て行なわれる。しかしながら、アミノピレン化合物は光
の可視領域において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 photoreceptor shown in FIG. 1 has a photosensitive layer 2 comprising an aminopyrene compound, a sensitizing dye, and a binder (binder resin) on a conductive support 1. The photoreceptor shown in FIG. The aminopyrene compound here acts as a photoconductive substance, and the generation and transfer of charge carriers necessary for light attenuation take place via the aminopyrene compound. However, aminopyrene compounds have almost no absorption in the visible region of light, so
For the purpose of forming an image using visible light, it is necessary to sensitize by adding a sensitizing dye that absorbs in the visible region.
第２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をアミノピレン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。ここでのアミノピレン化合物は結合剤（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当している。そして、
この感光体にあっては電荷発生物質とアミノピレン化合
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。The photoreceptor shown in FIG. 2 has a photosensitive layer 2' provided on a conductive support 1, in which a charge generating substance 3 is dispersed in a charge transporting medium 4 made of an aminopyrene compound and a binder. The aminopyrene compound here forms a charge transport medium together with the binder (or binder and plasticizer);
On the other hand, a charge generating substance 3 (a charge generating substance such as an inorganic or organic pigment) generates charge carriers. In this case, the charge transport medium 4 is mainly responsible for receiving charge carriers generated by the charge generating substance 3 and transporting them. and,
The basic condition for this photoreceptor is that the absorption wavelength regions of the charge generating substance and the aminopyrene 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.
一般式（Ｉ）で表わされるアミツノピレン化合物は可視
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物質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 amitunopyrene compound represented by the general formula (I) has almost no absorption in the visible region, and generally absorbs light in the visible region and is particularly effective as a charge transport material when combined with a charge generating substance 3 that generates charge carriers. 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／！Ｆ５と、アミノピレン
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。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Ｍ４（主としてアミノ
ピレン化合物が働く）で行なわれる。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。The photoreceptor shown in FIG. 3 generates charges mainly based on a charge generating substance 3 on a conductive support 1. A photosensitive layer 2' consisting of a laminated layer of F5 and a charge transport layer 4 containing an aminopyrene compound is provided. 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. In this case, the generation of charge carriers necessary for light attenuation is carried out in the charge generation substance 3,
Further, charge carriers are transported by a charge transport M4 (mainly acted by an aminopyrene compound). This mechanism is similar to the explanation given for the photoreceptor shown in FIG.
第４図における感光体は第３図の電荷発生層５とアミノ
ピレン化合物を含有する電荷搬送層４の積層順を逆にし
たものであり、その電荷担体の発生及び搬送の機構は上
記の説明と同様にできる。この場合機械的強度を考慮し
第５図の様に電荷発生層５の上に保護層６を設けること
もできる。The photoreceptor in FIG. 4 is obtained by reversing the stacking order of the charge generation layer 5 and the charge transport layer 4 containing an aminopyrene compound in FIG. 3, and the mechanism of charge carrier generation and transport is the same as the above explanation. You can do the same. In this case, in consideration of mechanical strength, a protective layer 6 may be provided on the charge generation layer 5 as 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ピレン化
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 aminopyrene compounds are dissolved in a solution containing a binder, and then a sensitizing agent 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.
感光層の厚さは３〜５０μｍ、好ましくは５〜２０ｐｍ
が適当である。感光層２に占めるアミノピレン化合物の
量は３０〜７０重量％、好ましくは約５０重量２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４ｇ−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２種以上が併用されても
よい。The thickness of the photosensitive layer is 3 to 50 μm, preferably 5 to 20 pm.
is appropriate. The amount of the aminopyrene compound in the photosensitive layer 2 is 30 to 70% by weight, preferably about 50% by weight2, and the amount of the sensitizing dye in the photosensitive layer 2 is 0.1 to 5% by weight, preferably 0.5% by weight. It is 5 to 3% by weight. As the sensitizing agent, Brilliant Green, Victoria Blue B,
triarylmethane dyes such as methyl violet, crystal violet, acid violet 6B,
Rhodamine B, Rhodamine 6G, Rhodamine G Extra, Eosin S, Erythrosin, Rose Bengal, xanthine dyes such as fluorescein, thiazine dyes such as methylene blue, cyanine dyes such as cyanine,
Examples include pyrylium dyes such as 2,6-diphenyl-4-(N,N-dimethylaminophenyl)thiapyrylium verchlorate and benzopyrylium salt (described in Japanese Patent Publication No. 4G-25658). Note that these sensitizing agents may be used alone or in combination of two 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種以上のアミノピレン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。In addition, 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 aminopyrene 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Ｍ２’の厚さは３〜５０μｍ、好ましくは５〜２０
μ濡が適当である。感光層２′に占めるアミノピレン化
合物の魚体１０〜９５重量２、好ましくは３０〜９０重
量％であり、また、感光Ｎ２’に占める電荷発生物質３
の量は０．１〜５０重量％、好ましくは１〜２ＯＮ量Ｘ
である。The thickness of photosensitive M2' is 3 to 50 μm, preferably 5 to 20 μm.
μ wet is appropriate. The aminopyrene compound accounts for 10 to 95% by weight2, preferably 30 to 90% by weight of the aminopyrene compound in the photosensitive layer 2', and the charge generating substance accounts for 3% in the photosensitive layer 2'.
The amount of is 0.1 to 50% by weight, preferably 1 to 2ON amount
It is.
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ＣＩ ２
１１８０）、シーアイピグメントレッド４１ （ＣＩ
２１２００）、シーアイアシッドレッド５２（ＣＩ ４
５１００）、シーアイベーシックレッド３（ＣＩ４５２
１０）、カルバゾール骨格を有するアゾ顔料（特開昭５
３−９５０３３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５３４３３４４５号公報）
、トリフェニルアミン骨格を有するアゾ顔料（特開昭５
３−１３２３４７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
格を有するアブ顔料（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
５４−１７７３３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（Ｃ
Ｉ ７４１００）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（ＣＩ ７３４１０）、シー
アイバットダイ（ＣＩ ７３０３０）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Ｉｆり、イン
ダンスレンスカーレットＲ（バイエル社製）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
。Examples of the charge generating substance 3 include inorganic pigments such as selenium, selenium-tellurium, cadmium sulfide, cadmium-selenium sulfide, and α-silicon, and examples of organic pigments include CI Pigment Blue 25 (Color Index CI 2).
1180), CI Pigment Red 41 (CI
21200), Sea Eye Acid Red 52 (CI 4
5100), CI Basic Red 3 (CI452)
10), an azo pigment having a carbazole skeleton (Japanese Patent Application Laid-Open No.
3-95033), an azo pigment having a distyrylbenzene skeleton (Japanese Unexamined Patent Publication No. 53433445)
, an azo pigment having a triphenylamine skeleton (Japanese Unexamined Patent Publication No. 5
3-132347), an azo pigment having a dibenzothiophene skeleton (described in JP-A-54-21728), an azo pigment having an oxadiazole skeleton (described in JP-A-54-12742), Abu pigments having a fluorenone skeleton (described in JP-A-54-22834), azo pigments having a bisstilbene skeleton (described in JP-A-54-17733), azo pigments having a distyryloxadiazole skeleton (described in JP-A-54-17733), Japanese Patent Publication No. 54-2129
Azo pigments such as C.I. Pigment Blue 16 (C
Phthalocyanine pigments such as C.I. Butt Brown 5 (CI 73410) and C.I. Butt Dye (CI 73030); ), etc. These charge generating substances may be used alone or in combination of two or more types.
更に、第３図に示した感光体は作製するには、導電性支
持体１以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
適当な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種以上のアミノピレン化合物と結合剤
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 one or more conductive supports, or fine particles 3 of a charge generating substance are deposited in a suitable solvent in which a binder is dissolved if necessary. The charge generation layer 5 is formed by coating the dispersion and drying it, and if necessary, performing surface finishing and film thickness adjustment by methods such as puff polishing, and then forming the charge generation layer 5 on which one or more of the The charge transport layer 4 may be formed by applying a solution containing two or more aminopyrene compounds and a binder and drying the solution. 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２閾以下
であり、電荷搬送層４の厚さは３〜５０よ、好ましくは
５〜２０癖が適当である。電荷発生層５が電荷発生層物
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ＦｆＩ５に
占める割合は１０〜９５重量２、好ましくは５０〜９０
重量ｘ程度である。また、電荷搬送層４に占める化合物
の量は１０〜９５重量２、好ましくは３０〜９０重量％
である。第４図に示した感光体を作成するには、導電性
支持体１上にアミノピレン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を形成したのち、
二の電荷搬送層の上に電荷発生層物質の微粒子を、必要
によって結合剤を溶解した溶媒中に分散した分散液をス
プレー塗工等の方法で塗布乾燥して電荷発生層５を形成
すればよい。電荷発生層あるいは電荷搬送層の量比は第
３図で説明した内容と同様である。このようにして得ら
れた感光体の電荷発生Ｎ５の上に更に適当な樹脂溶液を
スプレー塗工等の方法により保護／Ｗ６を形成すること
により第５図に示す感光体を作成できる。ここで用いる
樹脂としては、後記する結合剤が使用できる。The thickness of the charge generation layer 5 is 5 μm or less, preferably 2 thresholds or less, and the thickness of the charge transport layer 4 is suitably 3 to 50 μm, preferably 5 to 20 μm. If the charge generation layer 5 is of a type in which fine particles 3 of the charge generation layer material are dispersed in a binder, the proportion of the fine particles 3 of the charge generation material to the charge generation FfI5 is 10 to 95% by weight2, preferably 50-90
The weight is approximately x. The amount of the compound in the charge transport layer 4 is 10 to 95% by weight2, preferably 30 to 90% by weight.
It is. To create the photoreceptor shown in FIG. 4, a solution containing an aminopyrene compound and a binder is applied onto the conductive support 1 and dried to form the charge transport layer 4.
The charge generation layer 5 is formed by coating fine particles of the charge generation layer material on the second charge transport layer by a method such as spray coating with a dispersion of the charge generation layer material dispersed in a solvent in which a binder is dissolved if necessary. good. The amount ratio of the charge generation layer or the charge transport layer is the same as that explained with reference to FIG. A photoreceptor shown in FIG. 5 can be prepared by forming a protective layer W6 on the charge-generating N5 of the photoreceptor thus obtained by spray coating or the like with a suitable resin solution. As the resin used here, the binder described later can be used.
なお、これらのいずれの感光体製造においては導電性支
持体１に、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。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、維縁性でかつ接
着性のある樹脂はすべて使用できる。In the production of any of these photoreceptors, the conductive support 1 is made of a metal plate or metal foil such as aluminum, a plastic film on which metal such as aluminum is vapor-deposited,
Alternatively, paper that has been subjected to conductive treatment may be used. Also,
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 resin that is adhesive and has adhesive properties can be used.
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。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、必要に応して接着層又はバリヤｍ
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、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。Furthermore, the photoreceptor obtained as described above may have an adhesive layer or barrier layer between the conductive support and the photosensitive layer, if necessary.
can be provided. Materials used for these layers include polyamide, nitrocellulose, aluminum oxide, etc., 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。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 and exposed, then developed and, if necessary, transferred to paper or the like. The photoreceptor of the present invention has excellent advantages such as high sensitivity and flexibility.
以下、実施例により本発明を説明する。なお、下記実施
例において部はすべて重量部である。The present invention will be explained below with reference to Examples. In addition, in the following examples, all parts are parts by weight.
〔−形成（１）の化合物の合成〕
（化合物Ｎａ９の合成例）
７−ｔｅｒｔ−ブチル−１−ヨードピレン１ 、７６ｇ
（４、５８ｍｍｏＱ）、 ４．４’−ジメチルジフェ
ニルアミン１．８１ｇ（９，１６ｍｍ。[-Synthesis of compound of formation (1)] (Synthesis example of compound Na9) 7-tert-butyl-1-iodopyrene 1, 76 g
(4,58mmoQ), 4,4'-dimethyldiphenylamine 1.81g (9,16mm.
Ｑ、）、炭酸カリウム１．２７ｇ（９，１６ｍｍｏＱ）
及び銅粉０．２９ｇにニトロベンゼン２０ｍＱを加え窒
素気流下、エステル管で共沸脱水しながら、２０８℃で
２時間撹拌した。Q,), potassium carbonate 1.27g (9,16mmoQ)
Then, 20 mQ of nitrobenzene was added to 0.29 g of copper powder, and the mixture was stirred at 208°C for 2 hours under a nitrogen stream while being azeotropically dehydrated using an ester tube.
室温まで放冷した後、セライトを用いて濾過し。After cooling to room temperature, it was filtered using Celite.
濾液を減圧濃縮し、残渣にクロロホルムを加え、クロロ
ホルム層を水洗し、次いで硫酸マグネシウムで乾燥し、
更に減圧濃縮して暗褐色の油状物を得た。これをシリカ
ゲルカラム処理（溶離液；トルエン／ｎ−ヘキサン（１
：４）混合溶媒）し、エタノール／酢酸エチル混合溶媒
から再結晶して、黄色板状晶の下式で示される化合物Ｎ
Ｇ９の７−ｔｅｒｔ−ブチル−１−Ｎ。The filtrate was concentrated under reduced pressure, chloroform was added to the residue, the chloroform layer was washed with water, and then dried over magnesium sulfate.
Further concentration under reduced pressure gave a dark brown oil. This was treated with a silica gel column (eluent: toluene/n-hexane (1
:4) mixed solvent) and recrystallized from an ethanol/ethyl acetate mixed solvent to form yellow plate-like crystals of the compound N represented by the formula below.
7-tert-butyl-1-N of G9.
Ｎ−ビス（４−メチルフェニル）アミノピレン１．４０
ｇ（収率６７．７％） ヲ得た。融点ハ１９６．０−１
９７．０°Ｃであった。N-bis(4-methylphenyl)aminopyrene 1.40
g (yield 67.7%) was obtained. Melting point 196.0-1
The temperature was 97.0°C.
元素分析値はＣ３４Ｈ３１Ｎとして下記の通りであった
。The elemental analysis value was as follows as C34H31N.
０％ Ｈ％ Ｎ％
実測値 ９０．１９ ６．８３ ３．０８計算値 ９０
，０２ ６．８９ ３．０９Ｈ，Ｃ′ ゝＣＨ。0% H% N% Actual value 90.19 6.83 3.08 Calculated value 90
,02 6.89 3.09H,C' ゝCH.
なお、他のアミノピレン化合物も前記と同様に合成した
。Note that other aminopyrene compounds were also synthesized in the same manner as above.
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、ＣＩ ２１１８０）７６部、ポＩＪ ｘ
ステル樹脂（バイロン２００．■東洋紡績製）の２ｚ
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, CI 21180) as a charge generating substance, PoIJ x
2z of Stell resin (Byron 200.■ Manufactured by Toyobo)
1,260 parts of the tetrahydrofuran solution and 3,700 parts of tetrahydrofuran were pulverized and mixed in a ball mill, and the resulting dispersion was applied onto the aluminum surface of a conductive support made of a polyester base coated with aluminum using a doctor blade, and air-dried. A charge generation layer having a thickness of about 1 μm was formed.
一方、電荷搬送物質としては化合物具体例ＮＱＩのアミ
ノピレン化合物２部、ポリカーボネート樹脂（パンライ
トに１３００．■奇人製）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１２０°Ｃで５分間乾燥して厚さ約２０
μｍ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, as a charge transport substance, 2 parts of the aminopyrene compound of specific example NQI, 2 parts of polycarbonate resin (Panlite 1300.■ manufactured by Kijin), and 16 parts of tetrahydrofuran were mixed and dissolved to form a solution, which was then used to generate the charge. The layer was coated with a doctor blade and dried at 80°C for 2 minutes and then at 120°C for 5 minutes to a thickness of approx.
A photoreceptor Nα1 was prepared by forming a charge transport layer with a thickness of μm.
実施例２〜３３
電荷発生物質および電荷搬送物質（アミノピレン化合物
）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Ｎα２〜３１を作成した。Examples 2 to 33 Photoreceptors Nα2 to 31 were prepared in exactly the same manner as in Example 1, except that the charge generating substance and the charge transporting substance (aminopyrene compound) were replaced with those shown in Table 1.
さ約１μｌに真空蒸着して電荷発生層を形成せしめた。A charge generation layer was formed by vacuum evaporation in an amount of about 1 μl.
次いでＮＱ９のアミノピレン化合物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４９００
０）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Ｎα３４
を得た。Next, 2 parts of NQ9 aminopyrene compound, polyester resin (Polyester Adhesive 4900 manufactured by DuPont)
0) 3 parts and 45 parts of tetrahydrofuran are mixed and dissolved to prepare a charge transport layer forming liquid, and this is applied onto the above charge generation layer (selenium vapor deposited layer) using a doctor blade, air dried, and then heated under reduced pressure. Dry at the bottom to a thickness of about 10 μm
photoreceptor Nα34 of the present invention by forming a charge transport layer of
I got it.
実施例３５
セレンの代りにペリレン系顔料
実施例３４
厚さ約３００μｍのアルミニウム板上にセレンを厚を用
いて電荷発生層（但し、厚さは約０．６μｍ）を形成し
た、かつ電荷搬送物質としてアミノピレン化合物＆９を
用いた以外は実施例３４とまったく同様にして感光体Ｎ
α３５を作成した。Example 35 Perylene pigment instead of selenium Example 34 A charge-generating layer (however, the thickness is about 0.6 μm) was formed using selenium on an aluminum plate with a thickness of about 300 μm, and a charge transport material Photoreceptor N was prepared in exactly the same manner as in Example 34, except that aminopyrene compound &9 was used as
I created α35.
実施例３６
ダイアンプル−（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、これにアミノピレン化合物Ｎ
α９１２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、
１００℃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Ｎα３６を作成した。Example 36 A mixture of 1 part of diampoule (same as used in Example 1) and 158 parts of tetrahydrofuran was ground and mixed in a ball mill, and then aminopyrene compound N was added to the mixture.
A photosensitive layer forming liquid obtained by adding 12 parts of α9 and 18 parts of a polyester resin (Polyester Adhesive 49000 manufactured by DuPont) and further mixing was applied onto an aluminum vapor-deposited polyester film using a doctor blade,
A photoreceptor Nα36 of the present invention was prepared by drying at 100° C. for 30 minutes to form a photosensitive layer with a thickness of about 16 μm.
実施例３７
アルミニウム蒸着したポリエステルフィルム基板上に、
実施例１で用いた電荷搬送層塗工液を実施例１と同様に
してブレード塗工し、ついで乾燥して厚さ約２０μｍの
電荷搬送１を形成した。ビスアゾ顔料（Ｐ−２） １３
．５部、ポリビニルブチラール（商品名：ＸＹＨＬユニ
オンカーバイトプラスチック社製）５．４部、ＴＨＦ
６８０部及びエチルセロソルブ１０２０部をボールミル
中で粉砕混合した後、エチルセロソルブ１７００部を加
え攪拌混合して電荷発生層用塗工液を得た。この塗工液
を上記の電荷搬送層の上にスプレー塗工し、１００℃で
１０分間乾燥して厚さ約０．２癖の電荷発生層を形成し
た。さらにこの電荷発生層の上にポリアミド樹脂（商品
名：Ｃ阿−８０００、東し製）のメタノール／ｎ−ブタ
ノール溶液をスプレー塗工し１２０℃で３０分間乾燥し
て厚さ約０．５μ０の保護層を形成せしめて感光体Ｎα
３７を作成した。Example 37 On a polyester film substrate coated with aluminum,
The charge transport layer coating solution used in Example 1 was applied with a blade in the same manner as in Example 1, and then dried to form a charge transport layer 1 having a thickness of about 20 μm. Bisazo pigment (P-2) 13
．． 5 parts, polyvinyl butyral (product name: XYHL Union Carbide Plastics Co., Ltd.) 5.4 parts, THF
After pulverizing and mixing 680 parts of ethyl cellosolve and 1020 parts of ethyl cellosolve in a ball mill, 1700 parts of ethyl cellosolve was added and mixed with stirring to obtain a charge generation layer coating liquid. This coating solution was spray coated onto the above charge transport layer and dried at 100°C for 10 minutes to form a charge generation layer having a thickness of about 0.2 cm. Furthermore, a methanol/n-butanol solution of polyamide resin (trade name: C-A-8000, manufactured by Toshi) was spray-coated on top of this charge-generating layer, and dried at 120°C for 30 minutes to a thickness of about 0.5μ0. A protective layer is formed on the photoreceptor Nα.
37 was created.
かくしてつくられた感光体Ｎａｌ〜３７について、市販
の静電複写紙試験装置（ＫＫ川口電機製作所製５Ｐ４２
８型）を用いて一６ＫＶ又は＋６ＫＶのコロナ放電を２
０秒間行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４．５ル
ツクスになるよう照射してその表面電位がＶｐｏの１７
２になる迄の時間（秒）を求め、露光量Ｅ１／２（ルッ
クス・秒）を算出した。その結果を表−２に示す。The photoreceptor Nal~37 thus produced was tested using a commercially available electrostatic copying paper tester (5P42 manufactured by KK Kawaguchi Electric Seisakusho).
8) to generate a corona discharge of -6KV or +6KV.
After charging for 0 seconds, leave it in a dark place for 20 seconds.
Measure the surface potential Vpo (volts) at that time, then irradiate the photoreceptor surface with tungsten lamp light so that the illumination intensity is 4.5 lux, and the surface potential will be 17% of Vpo.
The time (seconds) until the value reached 2 was determined, and the exposure amount E1/2 (lux/second) 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
ＩＦ電せしめた後、原図を介して光照射を行って静電潜
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, each of the photoreceptors described above is subjected to IF electrophotography using a commercially available electrophotographic copying machine, and then light is irradiated through the original image to form an electrostatic latent image, which is developed using a dry developer. When the resulting 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
〔効 果〕
本発明の感光体は感光特性に優れていることは勿論の二
と、熱や機械的の衝撃に対する強度が犬で、しかも安価
に製造することができる。Table 2 [Effects] The photoreceptor of the present invention not only has excellent photosensitivity, but also has excellent resistance to thermal and mechanical shocks, and can be manufactured at low cost.
第１図〜第５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。
・導電性支持体
２ 、２＋ 、 ２ｕ、 ２＃、 ｔ）ｒｒｒｒ感光層
特許出願人 株式会社 リ コ1 to 5 are cross-sectional views enlarged in the thickness direction of an electrophotographic photoreceptor according to the present invention.・Conductive support 2, 2+, 2u, 2#, t)rrrr Photosensitive layer Patent applicant Rico Co., Ltd.
Claims (1)
るアミノピレン化合物の少なくとも１種を有効成分とし
て含有することを特徴とする電子写真用感光体。 ▲数式、化学式、表等があります▼（ I ） （式中、Ｒ＾１、Ｒ＾２は置換もしくは無置換のアルキ
ル基又は置換もしくは無置換のアリール基を表わす。）(1) An electrophotographic photoreceptor comprising at least one aminopyrene compound represented by the following general formula (I) as an active ingredient on a conductive support. ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (I) (In the formula, R^1 and R^2 represent a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2255906A JP3054659B2 (en) | 1990-09-25 | 1990-09-25 | Electrophotographic photoreceptor |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2255906A JP3054659B2 (en) | 1990-09-25 | 1990-09-25 | Electrophotographic photoreceptor |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH04133064A true JPH04133064A (en) | 1992-05-07 |
| JP3054659B2 JP3054659B2 (en) | 2000-06-19 |
Family
ID=17285216
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2255906A Expired - Fee Related JP3054659B2 (en) | 1990-09-25 | 1990-09-25 | Electrophotographic photoreceptor |
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| Country | Link |
|---|---|
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5495049A (en) * | 1993-03-22 | 1996-02-27 | Fuji Xerox Co., Ltd. | Triarylamine compounds useful in electrophotographic photoreceptors |
| US5604065A (en) * | 1994-09-14 | 1997-02-18 | Ricoh Company, Ltd. | Electrophotographic photoconductor and triphenylamine compound for use therein |
| US5856596A (en) * | 1994-02-23 | 1999-01-05 | Fuji Xerox Co., Ltd. | Process for preparing mono-iodinated aromatic compound |
| WO2004083162A1 (en) * | 2003-03-20 | 2004-09-30 | Idemitsu Kosan Co. Ltd. | Aromatic amine derivative and organic electroluminescent element made with the same |
| US7138555B2 (en) | 2004-04-20 | 2006-11-21 | Xerox Corporation | Process for preparing iodoaromatic compounds and using the same |
| US8709613B2 (en) | 2004-05-12 | 2014-04-29 | Idemitsu Kosan Co., Ltd. | Aromatic amine derivative, organic electroluminescent element employing the same, and process for producing aromatic amine derivative |
-
1990
- 1990-09-25 JP JP2255906A patent/JP3054659B2/en not_active Expired - Fee Related
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5495049A (en) * | 1993-03-22 | 1996-02-27 | Fuji Xerox Co., Ltd. | Triarylamine compounds useful in electrophotographic photoreceptors |
| US5587263A (en) * | 1993-03-22 | 1996-12-24 | Fuji Xerox Co., Ltd. | Electrophotographic photoreceptor using triarylamine compounds |
| US5856596A (en) * | 1994-02-23 | 1999-01-05 | Fuji Xerox Co., Ltd. | Process for preparing mono-iodinated aromatic compound |
| US5604065A (en) * | 1994-09-14 | 1997-02-18 | Ricoh Company, Ltd. | Electrophotographic photoconductor and triphenylamine compound for use therein |
| WO2004083162A1 (en) * | 2003-03-20 | 2004-09-30 | Idemitsu Kosan Co. Ltd. | Aromatic amine derivative and organic electroluminescent element made with the same |
| CN102516090A (en) * | 2003-03-20 | 2012-06-27 | 出光兴产株式会社 | Aromatic amine derivative and organic electroluminescent element using the same |
| US8592051B2 (en) | 2003-03-20 | 2013-11-26 | Idemitsu Kosan Co., Ltd. | Aromatic amine derivative and organic electroluminescent element made with the same |
| US7138555B2 (en) | 2004-04-20 | 2006-11-21 | Xerox Corporation | Process for preparing iodoaromatic compounds and using the same |
| US8709613B2 (en) | 2004-05-12 | 2014-04-29 | Idemitsu Kosan Co., Ltd. | Aromatic amine derivative, organic electroluminescent element employing the same, and process for producing aromatic amine derivative |
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| Publication number | Publication date |
|---|---|
| JP3054659B2 (en) | 2000-06-19 |
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