JPH0434437A - Electrophotographic sensitive body - Google Patents
Electrophotographic sensitive bodyInfo
- Publication number
- JPH0434437A JPH0434437A JP14088690A JP14088690A JPH0434437A JP H0434437 A JPH0434437 A JP H0434437A JP 14088690 A JP14088690 A JP 14088690A JP 14088690 A JP14088690 A JP 14088690A JP H0434437 A JPH0434437 A JP H0434437A
- Authority
- JP
- Japan
- Prior art keywords
- group
- photoreceptor
- charge
- alkylpyrene
- layer
- 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
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 18
- 125000003118 aryl group Chemical group 0.000 claims abstract description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 3
- 108091008695 photoreceptors Proteins 0.000 claims description 52
- 239000000126 substance Substances 0.000 claims description 22
- -1 olefin compound Chemical group 0.000 claims description 20
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 2
- 150000001336 alkenes Chemical class 0.000 abstract 1
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 66
- 150000001875 compounds Chemical class 0.000 description 35
- 230000032258 transport Effects 0.000 description 24
- 239000000049 pigment Substances 0.000 description 19
- 239000011230 binding agent Substances 0.000 description 17
- 239000000463 material Substances 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 239000002800 charge carrier Substances 0.000 description 10
- 239000000975 dye Substances 0.000 description 10
- 229920005989 resin Polymers 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- 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
- 239000011248 coating agent Substances 0.000 description 6
- 238000000576 coating method Methods 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- 230000001235 sensitizing effect Effects 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
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 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
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 229910052980 cadmium sulfide Inorganic materials 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000012860 organic pigment Substances 0.000 description 3
- 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 3
- 239000004014 plasticizer Substances 0.000 description 3
- 229920001225 polyester resin Polymers 0.000 description 3
- 239000004645 polyester resin Substances 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 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
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000005496 eutectics Effects 0.000 description 2
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 2
- 150000002430 hydrocarbons Chemical group 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
- 239000012046 mixed solvent Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- 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 2
- 229920003227 poly(N-vinyl carbazole) Polymers 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
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical class C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 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
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- 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
- 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
- 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
- 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
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-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
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 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
- 238000000862 absorption spectrum Methods 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
- 125000004653 anthracenylene group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 238000005452 bending Methods 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
- 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
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 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
- 125000005584 chrysenylene group Chemical group 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
- 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
- 230000007547 defect Effects 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[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
- 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
- 229940011411 erythrosine Drugs 0.000 description 1
- 239000004174 erythrosine Substances 0.000 description 1
- 235000012732 erythrosine Nutrition 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 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
- 125000005567 fluorenylene group Chemical group 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
- 229960002143 fluorescein Drugs 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
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 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
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([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
- 239000002609 medium Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 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
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 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
- 125000005562 phenanthrylene 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
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 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
- 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
- 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
- 238000010298 pulverizing process Methods 0.000 description 1
- 125000005548 pyrenylene 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
- 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
- 230000035939 shock Effects 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
- 238000001694 spray drying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000001308 synthesis method Methods 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
- 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
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229940075420 xanthine Drugs 0.000 description 1
Landscapes
- Photoreceptors In Electrophotography (AREA)
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、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 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 electrophotography 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
実状である。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。Incidentally, the reality is that each of the above-mentioned inorganic substances has many advantages, but also has various disadvantages. For example, selenium, which is currently widely used, fully satisfies the conditions (1) to (3) above, but the manufacturing conditions are difficult, the manufacturing cost is high, it is not flexible, and it cannot be processed into a belt shape. It also has disadvantages, such as being difficult to handle and being sensitive to heat and mechanical shock, requiring 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。Cadmium sulfide and zinc oxide are used as photoreceptors by being dispersed in resin as a binder.
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。It cannot be used repeatedly as it is because of mechanical defects such as smoothness, hardness, tensile strength, and abrasion resistance.
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−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
体く特開昭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-dolinitrofluorene-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
分満足しつ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
表わされるアルキル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感光層を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 a photoreceptor for electrophotography, comprising a photosensitive layer containing as an active ingredient at least one alkylpyrene compound represented by the following general formula (I) on a conductive support. be done.
(式中、A1は置換もしくは無置換の芳香族炭化水素基
を、A2は置換もしくは無置換のアルキル基又はアリー
ル基を、A3は水素原子、置換もしくは無置換のアルキ
ル基又はアリール基を表わす。m及びnは1もしくは2
の整数であり、■+n=3である。但し閣又はnが2の
とき、A″、A3もしくはA2はそれぞれ同一でも異な
っていてもよい。)本発明において感光層に含有させる
前記一般式(1)で表わされるアルキルピレン化合物は
、例えば、一般式(II)
(式中A1.A” 、A”、m及びnは前記と同じ、)
で表わされるオレフィン化合物を還元することにより容
易に製造される。前記合成法で得られる一般式(1)で
示されるアルキルピレン化合物を更に具体的に説明する
。(In the formula, A1 represents a substituted or unsubstituted aromatic hydrocarbon group, A2 represents a substituted or unsubstituted alkyl group or aryl group, and A3 represents a hydrogen atom, a substituted or unsubstituted alkyl group, or an aryl group. m and n are 1 or 2
is an integer, and ■+n=3. However, when n is 2, A'', A3, or A2 may be the same or different, respectively.) In the present invention, the alkylpyrene compound represented by the general formula (1) to be contained in the photosensitive layer is, for example, General formula (II) (wherein A1.A", A", m and n are the same as above)
It is easily produced by reducing the olefin compound represented by The alkylpyrene compound represented by the general formula (1) obtained by the above synthesis method will be explained in more detail.
前記一般式(I)において、A1の芳香族炭化水素基と
してはフェニレン基、ビフェニレン基、ターフェニリレ
ン基等の非縮合炭素環式の芳香族炭化水素基及び縮合多
環式炭化水素基が挙げられる。In the general formula (I), examples of the aromatic hydrocarbon group of A1 include non-fused carbocyclic aromatic hydrocarbon groups and fused polycyclic hydrocarbon groups such as a phenylene group, a biphenylene group, and a terphenylylene group.
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
レニレン基、インデニレン基、ナフチレン基、アズレニ
レン基、ヘプタレニレン基、ビフェニレニレン基、aS
−インダセニレン基、フルオレニレン基、S−インダセ
ニレン基、アセナフチレニレン基、プレイアデニレン基
、アセナフテニレン基、フェナレニレン基、フエナント
リレン基、アントリレン基、フルオランテニレン基、ア
セフェナントリレニレン基、アセアントリレニレン基、
トリフェニレニレン基、ピレニレン基、クリセニレン基
、及びナフタセニレン基等が挙げられる。In this case, the fused polycyclic hydrocarbon group preferably has a ring having 18 or less carbon atoms, such as a pentalenylene group, indenylene group, naphthylene group, azulenylene group, heptarenylene group, biphenylene group, aS
- indasenylene group, fluorenylene group, S-indacenylene group, acenaphthyleneylene group, preadenylene group, acenaphthenylene group, phenalenylene group, phenanthrylene group, anthrylene group, fluoranthenylene group, acephenanthrylenylene group, aceantrylenylene group ,
Examples include triphenylene group, pyrenylene group, chrysenylene group, and naphthacenylene group.
A2及びA3がアリール基の場合、上記芳香族炭化水素
基の1価基を挙げることができる。またA1、A2及び
A3には以下に示す置換基を有することができる。When A2 and A3 are aryl groups, monovalent groups of the above-mentioned aromatic hydrocarbon groups can be mentioned. Moreover, A1, A2 and A3 can have the following substituents.
(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、02〜Cよ、とりわけ01〜C8、
さらに好ましくはC0〜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、C1〜C4のアルコキシ基、フェニ
ル基又はハロゲン原子、C2〜C4のアルキル基もしく
は01−04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、i−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−エトキシエチル基、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 02-C, especially 01-C8,
More preferred are C0 to 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 C1-C4 alkoxy group, a phenyl group or a halogen atom, a C2-C4 alkyl group or an 01-04 alkoxy group. Specifically, methyl group, ethyl group,
n-propyl group, i-propyl group, t-butyl group, S-
butyl group, n-butyl group, i-butyl group, trifluoromethyl group, 2-hydroxyethyl group, 2-cyanoethyl group, 2-ethoxyethyl group, 2-methoxyethyl group, benzyl group, 4-chlorobenzyl group, Examples include 4-methylbenzyl group, 4-methoxybenzyl group, 4-phenylbenzyl group, and the like.
(3)アルコキシ基(−0R1);R工は(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 (-0R1); R 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〜C4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 C-C4 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(−sRt);R1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 (-sRt); R1 is (2
) represents an alkyl group defined in Specific examples include methylthio group, ethylthio group, phenylthio group, and 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、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01〜C
1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。R□とR2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
−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;
It may contain an alkoxy group of 1, an alkyl group of 01-04, or a halogen atom as a substituent. R□ and R2 may jointly form a ring, or may jointly form a ring 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 , a morpholino group, a eurolidyl group, and the like.
(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1等が挙
げられる。(7) Examples include alkylene dioxy groups and alkylene dithio groups such as methylene dioxy groups and methylene dithio groups.
また、A2及びA:lがアルキル基の場合、アルキル基
としては(2)の項で説明し゛たアルキル基が使用され
る。Further, when A2 and A:l are alkyl groups, the alkyl groups described in section (2) are used as the alkyl groups.
以下、一般式(1)で表わされるアルキルピレン化合物
の代表例を示す。Representative examples of the alkylpyrene compound represented by the general formula (1) are shown below.
(1) Fl、n=2
本発明の感光体は、上記のようなアルキルピレン化合物
の1種又は2種以上を感光層2(2’、2”、2’又は
2tr/7)に含有させたものであるが、これらアルキ
ル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。(1) Fl, n=2 The photoreceptor of the present invention contains one or more of the above alkylpyrene compounds in the photosensitive layer 2 (2', 2", 2' or 2tr/7). However, depending on how these alkylpyrene compounds are applied, the results shown in Figures 1, 2,
It can be used as shown in FIGS. 3, 4 or 5.
第1図における感光体は導電性支持体1上に化合物、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。ここでのアルキルピレン化合物は
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ルキルピレン化合物を介して行なわ
れる。しかしながら、アルキル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 a compound, a sensitizing dye, and a binder (binder resin) on a conductive support 1. The photoreceptor shown in FIG. The alkylpyrene compound here acts as a photoconductive substance, and the generation and transfer of charge carriers necessary for light attenuation take place via the alkylpyrene compound. However, alkylpyrene 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図における感光体は、導電性支持体1上に電荷発生
物質3をアルキル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。ここでのアルキル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ルキルピレ
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。The photosensitive member 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 alkylpyrene compound and a binder. . The alkylpyrene compound here is a binder (
or binders and plasticizers) form the charge transport medium, while the charge generating substance 3 (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. In this photoreceptor, the basic condition is that the absorption wavelength regions of the charge generating substance and the alkylpyrene compound do not overlap each other, mainly in the visible region.
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(1)で表わされるアルキル
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。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 alkylpyrene compound represented by the general formula (1) 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 material 3 that generates charge carriers. Its feature is that it works as a.
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、アルキルピレン化
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、電荷搬送層4(主としてアルキル
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 in FIG. 3 has a photosensitive layer 2 consisting of a conductive support 1, a charge generation layer 5 mainly composed of a charge generation substance 3, and a charge transport layer 4 containing an alkylpyrene 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. The charge carriers necessary for light attenuation are generated by a charge generation substance 3, and the charge carriers are transported by a charge transport layer 4 (mainly composed of an alkylpyrene 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とアルキ
ル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。The photoreceptor in FIG. 4 is obtained by reversing the layering order of the charge generation layer 5 and the charge transport layer 4 containing an alkylpyrene compound in FIG. 3, and the mechanism of charge carrier generation and transport is as explained above. You can do the same thing.
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。In this case, considering mechanical strength, the charge generation layer 5 is
A protective layer 6 can also be provided thereon.
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ルキルピレン
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 Figure 1, one or more alkylpyrene compounds are dissolved in a solution containing a binder, and this is further added The photosensitive layer 2 may be formed by preparing a liquid containing the photosensitive material, coating it on the conductive support 1, and drying it.
感光層の厚さは3〜50μm、好ましくは5〜20μ冨
が適当である。感光層2に占めるアルキルピレン化合物
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2種以上が併用されてもよ
い。The appropriate thickness of the photosensitive layer is 3 to 50 .mu.m, preferably 5 to 20 .mu.m thick. The amount of the alkylpyrene 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.
% by weight, preferably 0.5-3% by weight. Brilliant Green and Victoria Blue B are used as sensitizers.
, triarylmethane dyes such as methyl violet, crystal violet, acid violet 6B, xanthine dyes such as Rhodamine B, Rhodamine 6G, Rhodamine G Extra, Eosin S, erythrosine, rose bengal, fluorescein, thiazine dyes such as methylene blue, Cyanine dyes such as cyanine, pyrylium dyes such as 2,6-diphenyl-4-(N,N-dimethylaminophenyl)thiapyrylium verchlorate, benzopyrylium salts (described in Japanese Patent Publication No. 48-25658), etc. can be mentioned. 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種以上のアルキル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l上に塗布し乾燥して感光層2′を形成すれ
ばよい。Furthermore, 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 alkylpyrene compounds and a binder, and these are dispersed on a conductive support. The photosensitive layer 2' may be formed by coating the photosensitive layer 2' on the body 1 and drying it.
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′に占めるアルキルピレン
化合物の量は10〜95重量で、好ましくは30〜90
重量%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。The thickness of the photosensitive layer 2' is 3 to 50 μm, preferably 5 to 20 μm.
μm is appropriate. The amount of the alkylpyrene compound in the photosensitive layer 2' is 10 to 95% by weight, preferably 30 to 90% by weight.
% 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.
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53−133445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
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54−212
9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1例えばシーアイピグメントブルー16(
CI 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。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), azo pigments having a distyrylbenzene skeleton (Japanese Unexamined Patent Publication No. 53-133445), azo pigments having a triphenylamine skeleton (described in Unexamined Japanese Patent Application No. 53-132347), dibenzo Azo pigments having a thiophene skeleton (described in JP-A-54-21728), azo pigments having an oxadiazole skeleton (
(described in JP-A-54-12742), azo pigments having a fluorenone skeleton (described in JP-A-54-22834), azo pigments having a bisstilbene skeleton (described in JP-A-54-17733) , an azo pigment having a distyryloxadiazole skeleton (JP-A-54-212
9), azo pigments having a distyrylcarbazole skeleton (described in JP-A-54-14967), and azo pigments 1, such as C.I. Pigment Blue 16 (described in JP-A-54-14967)
Phthalocyanine pigments such as CI 74100), indigo pigments such as CI Butt Brown 5 (CI 73410) and CI Butt Dye (CI 73030).
アルゴスカーレットB(バイエル社製)、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 include perylene pigments such as Argo Scarlet B (manufactured by Bayer AG) and Indance Scarlet R (manufactured by Bayer AG). Note that 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種以上のアルキル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 types of alkylpyrene 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声以下
であり、電荷搬送層4の厚さは3〜50声、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の電荷発生層5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に占める化合物の量
は10〜95重量%、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上にアルキル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、こ
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層5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層6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 tones or less, and the thickness of the charge transport layer 4 is suitably 3 to 50 tones, preferably 5 to 20 tones. 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 in the charge generation layer 5 is preferably 10 to 95% by weight. is about 50 to 90% by weight. Further, the amount of the compound in the charge transport layer 4 is 10 to 95% by weight, preferably 30 to 90% by weight. To produce the photoreceptor shown in FIG. 4, a solution containing an alkylpyrene 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 may be formed by applying a dispersion of fine particles of the charge generation layer material in a solvent in which a binder is dissolved, if necessary, on the transport layer by a method such as spray coating and drying. The amount ratio of the charge generation layer or charge transport layer is the third
The contents are the same as those explained in the figure. A protective layer 6 is further formed on the charge generation layer 5 of the photoreceptor thus obtained by spray coating or the like with a suitable resin solution, thereby producing the photoreceptor shown in FIG. 5. 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
ツー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。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, potu-N-vinylcarbazole, and polyacrylamide are used, but the insulating properties Any resin that is large and adhesive 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、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, 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. 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.
〔実施1例〕 以下、実施例により本発明を説明する。なお。[Example 1] The present invention will be explained below with reference to Examples. In addition.
下記実施例において部はすべて重量部である。In the following examples, all parts are by weight.
〔一般式(1)の化合物の合成〕
(化合物Nα8の合成例)
1−(4−N、N−ジフェニルアミノスチリル)ピレン
2゜00gをテトラヒドロフラン20mQに溶かし、こ
れに5%パラジウム−炭素0.40gを加え、室温、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
終了後セライトを用いてろ過し、減圧濃縮して、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(1:2)混合溶媒コし、エタノール
/酢酸エチル混合溶媒から再結晶して無色柱状結晶の下
記式で示される。l−[2−(4−N、N−ジフェニル
アミノフェニル)エチル]ピレン1.71g(収率85
.1%)を得た。融点は121.5〜122.5℃であ
った。[Synthesis of compound of general formula (1)] (Synthesis example of compound Nα8) 2.00 g of 1-(4-N,N-diphenylaminostyryl)pyrene was dissolved in 20 mQ of tetrahydrofuran, and 5% palladium-carbon was added to the solution. 40 g was added, and hydrogenation was carried out in a large shaking hydrogenation apparatus at room temperature and 1 atm hydrogen pressure. After the hydrogenation was completed, the mixture was filtered through Celite and concentrated under reduced pressure to obtain an oily substance. This was treated with a silica gel column [eluent: toluene/n-hexane (1:2) mixed solvent] and then recrystallized from an ethanol/ethyl acetate mixed solvent to give colorless columnar crystals as shown by the following formula. l-[2-(4-N,N-diphenylaminophenyl)ethyl]pyrene 1.71 g (yield 85
.. 1%). The melting point was 121.5-122.5°C.
元素分析値(%)
CHN
実測値 91.17 5,64 2.90こ
の化合物の赤外線吸収スペクトル(KBr錠剤法)には
、出発原料であるオレフィン化合物における960cm
−”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 (%) CHN Actual value 91.17 5,64 2.90 The infrared absorption spectrum (KBr tablet method) of this compound shows a 960 cm
-" absorption based on the C-H out-of-plane bending vibration of the transolefin was observed to disappear.
なお、他のアルキルピレン化合物も前記と同様に合成し
た。Note that other alkylpyrene 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、ポリエステ
ル樹脂(バイロン200、■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, CI 21180) as a charge generating substance, 1260 parts of a 2% tetrahydrofuran solution of polyester resin (Vylon 200, manufactured by Toyobo Co., Ltd.) and 3700 parts of tetrahydrofuran were ground and mixed in a ball mill. The obtained 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 having a thickness of about 1 μm.
一方、電荷搬送物質としては化合物具体例Nα11のア
ルキルピレン化合物2部、ポリカーボネート樹脂(パン
ライトに1300、■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120℃で5分間乾燥して厚さ約2
0μm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 an alkylpyrene compound of Compound Specific Example Nα11, 2 parts of polycarbonate resin (Panlite 1300, manufactured by Teijin), and 16 parts of tetrahydrofuran were mixed and dissolved to form a solution, and this was mixed and dissolved to form a solution. Apply on the generation layer using a doctor blade and apply at 80%
℃ for 2 minutes, then dried at 120℃ for 5 minutes to a thickness of approx.
A photoreceptor Nα1 was prepared by forming a charge transport layer with a thickness of 0 μm.
実施例2〜33
電荷発生物質および電荷搬送物質(アルキルピレン化合
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Nα2−33を作成した。Examples 2 to 33 Photoreceptors Nα2-33 were prepared in exactly the same manner as in Example 1, except that the charge generating substance and the charge transporting substance (alkylpyrene compound) were replaced with those shown in Table 1.
実施例34
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Nα11のアルキルピレン化合物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10μ■
の電荷搬送層を形成せしめて、本発明の感光体Nα34
を得た。Example 34 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 alkylpyrene compound of Nα11, a 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 10μ■
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
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ルキルピレン化合物
NQIIを用いた以外は実施例34とまったく同様にし
て感光体Nα35を作成した。Example 35 Same as Example 34, except that a perylene pigment was used instead of selenium to form the charge generation layer (however, the thickness was about 0.6 μm), and an alkylpyrene compound NQII was used as the charge transport material. A photoreceptor Nα35 was prepared in the same manner.
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Nα11のアルキルピ
レン化合物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、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 that used in Example 1) and 158 parts of tetrahydrofuran was ground and mixed in a ball mill, and then 12 parts of an alkylpyrene compound of Nα11 and a polyester resin ( A photosensitive layer forming solution obtained by adding 18 parts of Polyester Adhesive 49000 (manufactured by DuPont) and further mixing was applied onto an aluminum-deposited polyester film using a doctor blade, and dried at 100°C for 30 minutes to form a thick film. A photoreceptor Nα36 of the present invention was prepared by forming a photoreceptor layer having a thickness of approximately 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
電荷搬送層を形成した。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−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:CM−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0.5Rの保護層を形成せしめて感光体NQ3
7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 with 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 DEG C. for 10 minutes to form a charge generation layer having a thickness of about 0.2 mm. Furthermore, a methanol/n-butanol solution of polyamide resin (trade name: CM-8000, manufactured by Toshi) was spray coated on top of this charge generation layer and dried at 120°C for 30 minutes to protect the layer to a thickness of about 0.5R. Photoreceptor NQ3 by forming a layer
7 was created.
かくしてつくられた感光体N(11〜37について、市
販の静電複写紙試験装置(KK川日日電機製作所製5P
428型を用いて一6KV又は+6KVのコロナ放電を
20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1
72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。Photoreceptors N (11 to 37) thus produced were tested using a commercially available electrostatic copying paper tester (KK Kawahi Nichi Denki Seisakusho 5P).
After electrifying the photoreceptor by performing corona discharge of 16KV or +6KV for 20 seconds using Model 428, the surface potential Vpo (volts) at that time was measured after being left in a dark place for 20 seconds. Surface illuminance is 4.5
lux so that the surface potential is 1 of Vpo.
The time (seconds) until the temperature reached 72 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
帯電せしめた後、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, after each of the above-mentioned photoreceptors 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 5・・・電荷発生層 6・・・保護層Table-2 5... Charge generation layer 6...Protective layer
Claims (1)
るオレフィン化合物の少なくとも1種を有効成分として
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。 ▲数式、化学式、表等があります▼( I ) (式中、A^1は置換もしくは無置換の芳香族炭化水素
基を、A^2は置換もしくは無置換のアルキル基又はア
リール基を、A^3は水素原子、置換もしくは無置換の
アルキル基又はアリール基を表わす。m及びnは1もし
くは2の整数であり、m+n=3である。但しm又はn
が2のとき、A^1、A^3もしくはA^2はそれぞれ
同一でも異なっていてもよい。)(1) A photoreceptor for electrophotography, comprising a photosensitive layer containing at least one olefin 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, A^1 is a substituted or unsubstituted aromatic hydrocarbon group, A^2 is a substituted or unsubstituted alkyl group or aryl group, A ^3 represents a hydrogen atom, a substituted or unsubstituted alkyl group, or an aryl group.m and n are integers of 1 or 2, and m+n=3.However, m or n
When is 2, A^1, A^3, or A^2 may be the same or different. )
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2140886A JP3054657B2 (en) | 1990-05-30 | 1990-05-30 | Electrophotographic photoreceptor |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2140886A JP3054657B2 (en) | 1990-05-30 | 1990-05-30 | Electrophotographic photoreceptor |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH0434437A true JPH0434437A (en) | 1992-02-05 |
JP3054657B2 JP3054657B2 (en) | 2000-06-19 |
Family
ID=15279068
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2140886A Expired - Fee Related JP3054657B2 (en) | 1990-05-30 | 1990-05-30 | Electrophotographic photoreceptor |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP3054657B2 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2012027072A (en) * | 2010-07-20 | 2012-02-09 | Ricoh Co Ltd | Electrophotographic photoreceptor, and electrophotographic method, electrophotographic device and process cartridge using the same |
-
1990
- 1990-05-30 JP JP2140886A patent/JP3054657B2/en not_active Expired - Fee Related
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2012027072A (en) * | 2010-07-20 | 2012-02-09 | Ricoh Co Ltd | Electrophotographic photoreceptor, and electrophotographic method, electrophotographic device and process cartridge using the same |
Also Published As
Publication number | Publication date |
---|---|
JP3054657B2 (en) | 2000-06-19 |
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