JPH04118658A - Electrophotographic sensitive body - Google Patents
Electrophotographic sensitive bodyInfo
- Publication number
- JPH04118658A JPH04118658A JP17556190A JP17556190A JPH04118658A JP H04118658 A JPH04118658 A JP H04118658A JP 17556190 A JP17556190 A JP 17556190A JP 17556190 A JP17556190 A JP 17556190A JP H04118658 A JPH04118658 A JP H04118658A
- Authority
- JP
- Japan
- Prior art keywords
- group
- photoreceptor
- charge
- diaminopyrene
- compound
- 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 11
- 125000003118 aryl group Chemical group 0.000 claims abstract description 7
- 108091008695 photoreceptors Proteins 0.000 claims description 55
- -1 diaminopyrene compound Chemical class 0.000 claims description 50
- 239000000126 substance Substances 0.000 claims description 21
- 239000004480 active ingredient Substances 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 18
- BUAWIRPPAOOHKD-UHFFFAOYSA-N pyrene-1,2-diamine Chemical compound C1=CC=C2C=CC3=C(N)C(N)=CC4=CC=C1C2=C43 BUAWIRPPAOOHKD-UHFFFAOYSA-N 0.000 abstract description 2
- OWJJRQSAIMYXQJ-UHFFFAOYSA-N pyrene-1,6-diamine Chemical compound C1=C2C(N)=CC=C(C=C3)C2=C2C3=C(N)C=CC2=C1 OWJJRQSAIMYXQJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 66
- 230000032258 transport Effects 0.000 description 22
- 239000000049 pigment Substances 0.000 description 18
- 239000011230 binding agent Substances 0.000 description 16
- 150000001875 compounds Chemical class 0.000 description 14
- 239000002800 charge carrier Substances 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000000975 dye Substances 0.000 description 9
- 229920005989 resin Polymers 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 239000010419 fine particle Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- JSTHREDTMPIBEX-UHFFFAOYSA-N pyrene-2,7-diamine Chemical class C1=C(N)C=C2C=CC3=CC(N)=CC4=CC=C1C2=C43 JSTHREDTMPIBEX-UHFFFAOYSA-N 0.000 description 6
- 229910052711 selenium Inorganic materials 0.000 description 6
- 239000011669 selenium Substances 0.000 description 6
- 241000287531 Psittacidae Species 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 238000001035 drying 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
- 230000001235 sensitizing effect Effects 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction 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
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 229910052980 cadmium sulfide Inorganic materials 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000012860 organic pigment Substances 0.000 description 3
- 239000004014 plasticizer Substances 0.000 description 3
- 229920001225 polyester resin Polymers 0.000 description 3
- 239000004645 polyester resin Substances 0.000 description 3
- 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
- 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
- 239000000853 adhesive Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 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
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 239000001023 inorganic pigment Substances 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
- 239000011368 organic material Substances 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
- 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
- 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
- 125000004178 (C1-C4) alkyl 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
- 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
- UDHAWRUAECEBHC-UHFFFAOYSA-N 1-iodo-4-methylbenzene Chemical compound CC1=CC=C(I)C=C1 UDHAWRUAECEBHC-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
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)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
- 101150072353 CAPN3 gene Proteins 0.000 description 1
- 102100032539 Calpain-3 Human genes 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
- 235000000177 Indigofera tinctoria Nutrition 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- 239000004419 Panlite Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- JSQFXMIMWAKJQJ-UHFFFAOYSA-N [9-(2-carboxyphenyl)-6-(ethylamino)xanthen-3-ylidene]-diethylazanium;chloride Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(NCC)=CC=C2C=1C1=CC=CC=C1C(O)=O JSQFXMIMWAKJQJ-UHFFFAOYSA-N 0.000 description 1
- 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
- 239000012790 adhesive layer Substances 0.000 description 1
- 239000004840 adhesive resin Substances 0.000 description 1
- 229920006223 adhesive resin Polymers 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
- 125000003277 amino 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
- 125000002029 aromatic hydrocarbon 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
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
- 229960001506 brilliant green Drugs 0.000 description 1
- HXCILVUBKWANLN-UHFFFAOYSA-N brilliant green cation Chemical compound C1=CC(N(CC)CC)=CC=C1C(C=1C=CC=CC=1)=C1C=CC(=[N+](CC)CC)C=C1 HXCILVUBKWANLN-UHFFFAOYSA-N 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 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
- 239000003795 chemical substances by application Substances 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
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 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
- 238000005516 engineering process Methods 0.000 description 1
- YQGOJNYOYNNSMM-UHFFFAOYSA-N eosin Chemical compound [Na+].OC(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C(O)=C(Br)C=C21 YQGOJNYOYNNSMM-UHFFFAOYSA-N 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- IINNWAYUJNWZRM-UHFFFAOYSA-L erythrosin B Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=CC=C1C1=C2C=C(I)C(=O)C(I)=C2OC2=C(I)C([O-])=C(I)C=C21 IINNWAYUJNWZRM-UHFFFAOYSA-L 0.000 description 1
- 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
- 230000005496 eutectics Effects 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
- 150000004820 halides Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 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
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 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
- 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
- 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
- 238000002156 mixing Methods 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- DTPSXFMGMQOVTG-UHFFFAOYSA-N n-[4-[3-(2-aminocyclopropyl)phenoxy]-1-(benzylamino)-1-oxobutan-2-yl]benzamide Chemical compound NC1CC1C1=CC=CC(OCCC(NC(=O)C=2C=CC=CC=2)C(=O)NCC=2C=CC=CC=2)=C1 DTPSXFMGMQOVTG-UHFFFAOYSA-N 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
- 101150022123 ncl-1 gene Proteins 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
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 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
- 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
- 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
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 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
- 238000010992 reflux Methods 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
- 150000003839 salts Chemical class 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
- 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
- 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
- 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。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 refers to
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。A photoconductive photoreceptor is first charged in a dark place, for example by corona discharge, and then imagewise exposed to selectively dissipate the charge only in the exposed areas to obtain an electrostatic latent image, and this latent image area is treated with a dye. This is one of the image forming methods in which an image is formed by developing and visualizing electrostatic fine particles (toner) composed of a coloring material such as a pigment and a binder such as a polymeric substance.
このような電子写真法において感光体に要求される基本
的な特性としては、（１）暗所で適当な電位に帯電でき
ること、（２）暗所において電荷の逸散が少ないこと、
（３）光照射によって速やかに電荷を逸散せしめうろこ
となどがあげられる。The basic characteristics required of a photoreceptor in such an electrophotographic method are (1) ability to be charged to an appropriate potential in a dark place, (2) less dissipation of charge in a dark place,
(3) Examples include scales that quickly dissipate charge when irradiated with light.
ところで、前記の無機物質はそれぞれが多くの長所をも
っていると同時に、さまざまな欠点をも有しているのが
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、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、種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く特公昭４８−
２５６５８号公報に記載）、有機顔料を主成分とする感
光体（特開昭４７−３７５４３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
４７−１０７３５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３，１８
０，７３０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５
３−２７０３３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 organic materials, and some of them are in practical use. For example, a photoreceptor made of poly-N-vinylcarbazole and 2,4,7-dolinitrofluoren-9-one (US Pat. No. 3,484,237)
(described in the specification), a photoreceptor made by sensitizing poly-N-vinylcarbazole with a pyrylium salt dye.
25658), 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) -10735), a photoreceptor made by dye-sensitizing a triphenylamine compound (U.S. Patent No. 3,18
0,730), a photoreceptor using an amine derivative as a charge transporting material (JP-A-57-195254), a photoreceptor using poly-N-vinylcarbazole and an amine derivative as a charge-transporting material (JP-A-Sho 58- Publication No. 1155)
, 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 Patent Application Publication No. 1973
3-27033). 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 find anything that satisfies us.
一方、ジアミノピレン系化合物としては、Ｎ、Ｎ。On the other hand, examples of diaminopyrene compounds include N and N.
Ｎ’、Ｎ’−テトラフェニル−１，６−ジアミノピレン
化合物を用いた電子写真用感光体が特開昭５５−１４４
２５０に開示されている。しかし、上記化合物は接着樹
脂溶液に対して、難溶であり、前記、電子写真法におい
て感光体に要求される諸条件を満たす良好な感光層を形
成するには極めて、困難なものである。An electrophotographic photoreceptor using a N',N'-tetraphenyl-1,6-diaminopyrene compound was disclosed in JP-A-55-144.
250. However, the above-mentioned compound is poorly soluble in the adhesive resin solution, and it is extremely difficult to form a good photosensitive layer that satisfies the various conditions required for the photoreceptor in the electrophotographic method described above.
本発明の目的は、先に述べた従来の感光体のもつ種々の
欠点を解消し、電子写真法において要求される条件を十
分満足しうる感光体を提供することにある。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 provide a photoreceptor that can overcome the various drawbacks of the conventional photoreceptors mentioned above and fully satisfy the conditions required in electrophotography. Another object of the present invention is to provide an electrophotographic photoreceptor that is easy to manufacture, relatively inexpensive, and has excellent durability.
本発明によれば、導電性支持体上に下記一般式（１）で
表わされるジ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 diaminopyrene compound represented by the following general formula (1) on a conductive support. be done.
（式中、Ｒ１及びＲ２は、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し、各々同一でも異なってい
てもよい。ただし、１，６−ジアミノ化合物を除く。）
本発明において、感光層に含有させる前記一般式（１）
で表わされるジアミノピレン化合物は例えばＲ１＝Ｒ”
の場合
下式（ＩＩ）
で表わされるジアミノピレンと、
一般式（ｎｕ）
Ｘ−Ｒ” （ｏｒ Ｒ２）
（ｎｌ）（Ｒ１、Ｒ２は前記と同じ。Ｘはハロゲン
を表わす）で表わされるハロゲン化物とを反応させるか
、もしくは、一般式（ＩＶ）
（Ｘはハロゲンを表わす。(In the formula, R1 and R2 represent substituted or unsubstituted alkyl groups or aryl groups, and may be the same or different. However, excluding 1,6-diamino compounds.) In the present invention, in the photosensitive layer, The general formula (1) to be contained
For example, the diaminopyrene compound represented by R1=R"
In the case of diaminopyrene represented by the following formula (II) and the general formula (nu)
(nl) (R1 and R2 are the same as above. X represents a halogen) or react with a halide represented by the general formula (IV) (X represents a halogen).
で表わされるジハロゲンピレン誘導体と、一般式（Ｖ）
（Ｒ”、Ｒ２は前記と同じ）
で表わされるアミン誘導体を反応させることにより容易
に製造される。It is easily produced by reacting a dihalogenpyrene derivative represented by the formula (V) with an amine derivative represented by the general formula (V) (R" and R2 are the same as above).
前記一般式（１）において、Ｒ１、Ｒ２がアリール基の
場合の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
式炭化水素基が挙げられる。In the general formula (1), specific examples when R1 and R2 are aryl groups include non-fused carbocyclic aromatic groups such as phenyl group, biphenyl group, and terphenyl group, and fused polycyclic hydrocarbon groups. Can be mentioned.
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、ビフエニレニル基、ａＳ−インダセニ
ル基、フルオレニル基、Ｓ−インデニル基、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、アセフエナントリレニル基、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, biphenylenyl group, aS-indacenyl group, fluorenyl group, S-indenyl 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.
また、上記芳香族炭化水素基は以下に示すような置換基
を有するものも含まれる。Further, the above-mentioned aromatic hydrocarbon 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、０２〜０１□とりわけＣ工〜Ｃ８、
さらに好ましくはＣ□−０４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〜Ｃ４のアルコキシ基、フェニ
ル基又はハロゲン原子、Ｃ１〜Ｃ４のアルキル基もしく
はＣ工〜Ｃ，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。(1) Halogen atom, cyano group, nitro group (2) Alkyl group, preferably 02-01□ Especially C-C8,
More preferably, it is a C□-04 linear or branched alkyl group, 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-C4 alkoxy group, a phenyl group, or a halogen atom, a C1-C4 alkyl group, or a C-C4 alkoxy group. Specifically, methyl group, ethyl group,
n-propyl group, i-propyl group, t-butyl group, S-
Butyl group, n-butyl group.
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。i-butyl group, trifluoromethyl group, 2-hydroxyethyl group, 2-cyanoethyl group, 2-ethoxyethyl group, 2-methoxyethyl group, benzyl group, 4-chlorobenzyl group, 4-methylbenzyl group, 4- Examples include methoxybenzyl group and 4-phenylbenzyl group.
（３）アルコキシ基（−０Ｒ１）；Ｒ，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、０１〜Ｃ。(4) Aryloxy group Niaryl groups include phenyl and naphthyl groups. This is 01-C.
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。may contain an alkoxy group of 01 to 04, or a halogen atom as a substituent. Specifically, phenoxy group, 1-naphthyloxy group, 2-naphthyloxy group, 4-methylphenoxy group, 4-methoxyphenoquino group, 4-chlorophenoxy group, 6-methyl-2-naphthyloxy group, etc. Can be mentioned.
（５）アルキルメルカプト基（−５Ｒよ）；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 (-5R); 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
，のアルコキシ基、０１〜Ｃ４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Ｒ１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;
, an alkoxy group of 01 to C4, or a halogen atom as a substituent. R2 and R1 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、Ｒ１又はＲ２がアルキル基の具体例としては、た
とえば前記（２）の項で説明したアルキル基と同様なも
のが挙げられる。Further, specific examples of an alkyl group for R1 or R2 include the same alkyl groups as explained in the above (2).
以下、一般式（１）で表わされるジアミノピレン化合物
の代表例を示す。Representative examples of the diaminopyrene compound represented by the general formula (1) are shown below.
一０Ｉ４ら２ 化合物歯 置換位置− １，３− 一−Ｌ−一 −ｃ２Ｈ９ −ＯＩ２−Ｃ’ （１・ −−」を−一 Ｃ２Ｈｓ −ＣＨ，−０） −ＣＨ２−◎ 一心 １．３− １．３− １．３− １．３− 一〇缶３ （トＨ５ （（ト ００鴎Ｈ５ 一〇へ （トＨ５ 一〇偽 −Ｑ−Ｑ−ｃ、Ｈ。10I4 et al.2 Compound tooth Substitution position- 1,3- 1-L-1 -c2H9 -OI2-C' (1・ --"-1 C2Hs -CH, -0) -CH2-◎ single-mindedness 1.3- 1.3- 1.3- 1.3- 10 cans 3 (G H5 ((to 00 seagull H5 To 10 (G H5 10 false -Q-Q-c, H.
化合物＆
置換位置−
一計−
ｍ−」巳−一
１．３−
１．３−
ＧＣＱ
Ｆ
Ｑ−ＣＱ
−Ｃ＞Ｆ
１．３−
１．３−
−Ｇ−Ｏ）−０１，−Ｇ−Ｏ）−ｃ！（−（８）昧５−
００鵡Ｈ５
１，８−
１，８−
１，８−
一〇
−Ｏ１，−Ｑ
−Ｃ２Ｈ。Compound & Substitution position - total - m-" 1.3- 1.3- GCQ F Q-CQ -C>F 1.3- 1.3- -G-O)-01, -G- O)-c! (-(8) maj5-
00 Parrot H5 1,8- 1,8- 1,8- 10-O1,-Q -C2H.
一〇喰・ １．８− −Ｑ−Ｃ）Ｉ。10 yen・ 1.8- -Q-C)I.
−０−汎 化合物歯 置換位置− 一計− ◇００Ｉ３ −ｏ−ＯＣＨ３ 一〇心□ −０１）−Ｃ＞ＣＩ（。-0-pan compound teeth Substitution position − A sum- ◇00I3 -o-OCH3 10 hearts□ -01) -C>CI(.
−ｏ−Ｃ４Ｈ９を ｍ−」巳−一 一〇 一〇幌 −ＧＣ＞ＣＨ− ０福１ 詞 １．４− −か （ト。-o-C4H9 m-” Mi-ichi 10 Ipporo -GC>CH- 0 fortune 1 words 1.4- - or (to.
謔 １．４− １．４− １．４− （ト・ −ｑ鴎Ｈ７ｎ （ド ◇ −ＧＣ−Ｈ，− 化合物＆ 置換位置−Ｒ１ ３９１，４−−Ｃ−叫 ４０ ２．７− −〇 ４１ ２．７− −◎倶 一０幌 一◎ −か −ｏ−ｏＣＨ３ 一◎偽Ｈ５ （鵡 −Ｃ＞ＯＣＨ。Song 1.4- 1.4- 1.4- (to· -q Uh H7n (Do ◇ -GC-H,- Compound & Substitution position -R1 391,4--C-scream 40 2.7- - - 41 2.7- -◎〶 10 hood One◎ - Or -o-oCH3 1◎Fake H5 (Parrot -C>OCH.
一〇鵡Ｈ５ ２，７− −ｏ−ｏ−Ｃ２Ｈ６ −Ｇ−Ｃ’ｌ。10 parrot H5 2,7- -o-o-C2H6 -G-C'l.
４．９− り 化合物＆ 一計一 −Ｑ−ＣＩ（。4.9- the law of nature Compound& One total -Q-CI(.
−ｏ−Ｃ４Ｈ９ｔ −０◎鵡Ｈ５ ｍ−」巳−一 −Ｃ＞ＣＨ。-o-C4H9t -0◎Parrot H5 m-” Mi-ichi -C>CH.
−Ｑ−（，１（、を 一００鵡Ｈ５ ４，９− １，２− １，２− Ｕち −０）−ＣＨ２−◎ −ｃ２１（。-Q-(,1(, 100 parrot H5 4,9- 1,2- 1,2- Uchi -0)-CH2-◎ -c21(.
一島一〇
−０）−ＣＨ，−〇
−（，２Ｈ３
一〇
１．２−
■、２−
一０偶 −か
（（ト −◎（１３
化金物＆
領
置換位置−
１，２−
一計一
ｏｃＨ３
−Ｏ）−ＯＣＨ３
本発明の感光体は、上記のようなジアミノピレン化合物
の１種又は２種以上を感光層２ （２’ 、 ２”、
２”又は２１１１１）に含有させたものであるが、これ
らジ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。One island 〇-0) -CH, -〇-(,2H3 101.2- Total of ocH3 -O)-OCH3 The photoreceptor of the present invention contains one or more of the above-mentioned diaminopyrene compounds in the photosensitive layer 2 (2', 2'',
2" or 21111), but depending on how these diaminopyrene compounds are applied,
It can be used as shown in FIGS. 2, 3, 4, or 5.
第１図における感光体は導電性支持体１上にジアミノピ
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。The photoreceptor shown in FIG. 1 has a photosensitive layer 2 comprising a diaminopyrene compound, a sensitizing dye, and a binder (binder resin) on a conductive support 1. The photoreceptor shown in FIG.
ここでのジ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ジア
ミノピレン化合物を介して行なわれる。しかしながら、
ジ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 diaminopyrene compound here acts as a photoconductive substance, and the generation and transfer of charge carriers necessary for light attenuation take place via the diaminopyrene compound. however,
Since the diaminopyrene compound has almost no absorption in the visible region of light, in order to form an image with visible light, it is necessary to sensitize it by adding a sensitizing dye that has absorption 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をジ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。ここでのジ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ジアミノピレ
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。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 a diaminopyrene compound and a binder. . The diaminopyrene 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 diaminopyrene 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（Ｉ）で表わされるジアミノ
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。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 diaminopyrene compound represented by the general formula (I) has almost no absorption in the visible region, generally absorbs light in the visible region, and is particularly effective as a charge transport material when combined with the 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、ジアミノピレン化
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、電荷搬送層４（主としてジアミノ
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 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 a diaminopyrene 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 a diaminopyrene 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［５とジアミ
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。The photoreceptor in FIG. 4 is obtained by reversing the stacking order of the charge carrier generation [5] and the charge transport layer 4 containing the diaminopyrene compound in FIG. 3, and the mechanism of charge carrier generation and transport is as explained above. You can do it similarly.
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ジアミノピレン
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. 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３〜５０μ璽、好ましくは５〜２０μｍ
が適当である。感光層２に占めるオレフィン化合物の量
は３０−７０重量％、好ましくは約５０重量％であり。The thickness of the photosensitive layer is 3 to 50 μm, preferably 5 to 20 μm.
is appropriate. The amount of the olefin compound in the photosensitive layer 2 is 30-70% by weight, preferably about 50% by weight.
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、ベンゾビリリウ
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 amount of the sensitizing dye in the photosensitive layer 2 is 0.1-5% by weight, preferably 0.5-3% by weight. The sensitizers include triarylmethane dyes such as brilliant green, Victoria blue B, methyl violet, crystal violet, acid violet 6B, rhodamine B, rhodamine 6G, rhodamine G extra, eosin S, erythrosin, rose bengal, and fluorescein. xanthine dyes such as, thiazine dyes such as methylene blue, cyanine dyes such as cyanine, 2
, 6-diphenyl-4-(N,N-dimethylaminophenyl)thiapyrylium verchlorate, benzobyrylium salt (described in Japanese Patent Publication No. 48-25658), and other pyrylium dyes. 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種以上のジ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 diaminopyrene 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３〜５０μし好ましくは５〜２０μ
−が適当である。感光層２′に占めるジアミノピレン化
合物の量は１０〜９５重量％、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２、好ましくは１〜２０重量％
である。The thickness of the photosensitive layer 2' is 3 to 50μ, preferably 5 to 20μ.
- is appropriate. The amount of the diaminopyrene compound in the photosensitive layer 2' is 10 to 95% by weight, preferably 30 to 90% by weight, and the amount of the charge generating substance 3 in the photosensitive layer 2' is 10 to 95% by weight, preferably 30 to 90% by weight.
The amount of is 0.1 to 50% by weight2, preferably 1 to 20% by weight.
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 （ＣＩ４５
２１０）、カルバゾール骨格を有するアゾ顔料（特開昭
５３−９５０３３号公報に記載）、ジスチリルベンゼン
骨格を有するアゾ顔料（特開昭５３−１３３４４５号公
報）、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５４−２１
２９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
（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、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 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 (CI45
210), azo pigments having a carbazole skeleton (described in JP-A-53-95033), azo pigments having a distyrylbenzene skeleton (JP-A-53-133445), azo pigments having a triphenylamine skeleton ( (described in JP-A-53-132347), azo pigments with a dibenzothiophene skeleton (described in JP-A-54-21728), azo pigments with an oxadiazole skeleton (described in JP-A-54-12742), ), azo pigments having a fluorenone skeleton (described in JP-A No. 54-22834), azo pigments having a bisstilbene skeleton (described in JP-A-54-17733), and distyryloxadiazole skeletons. Azo pigment (JP-A-54-21
29), an azo pigment having a distyrylcarbazole skeleton (described in JP-A-54-14967)
Azo pigments such as C.I. Pigment Blue 16
(CI 74100), e.g. Sea Eye Butt Brown 5 (CI 73410),
Examples include indigo pigments such as CI Bat Dye (CI 73030), and perylene pigments such as Argo Scarlet B (manufactured by Bayer) and Indance Scarlet R (manufactured by Bayer). 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種以上のジ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 diaminopyrene 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５μＩ以下、好ましくは２牌以下
であり、電荷搬送層４の厚さは３〜５０癖、好ましくは
５〜２０声が適当である。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上にジ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、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 μI or less, preferably 2 μI or less, and the thickness of the charge transport layer 4 is suitably 3 to 50 microns, preferably 5 to 20 microns. 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 a diaminopyrene 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
リ−Ｎ−ビニルカルバゾール、ポリアクリルアミドのよ
うなビニル重合体などが用いられるが、絶縁性でかつ接
着性のある樹脂はすべて使用できる。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 a 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 with 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.
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.
〔一般式（１）の化合物の合成〕
（化合物覧２５の合成例）
１．８−ジアミノピレン０．７０ｇ、４−ヨードトルエ
ン２０．９３ｇ、炭酸カリウム２．４９ｇ及び銅粉０．
１９ｇを窒素気流下、共沸脱水しながら２０９℃で５時
間撹拌した。[Synthesis of compound of general formula (1)] (Synthesis example of compound list 25) 1.8-diaminopyrene 0.70 g, 4-iodotoluene 20.93 g, potassium carbonate 2.49 g, and copper powder 0.
19 g was stirred at 209° C. for 5 hours under a nitrogen stream while performing azeotropic dehydration.
室温まで放冷した後セライトを用いて濾過し、濾液にク
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（１：３）混合溶媒〕し、エタノール／
〜、〜ジメチルホルムアミド混合溶媒から再結晶して、
黄緑色針状結晶を得た。After cooling to room temperature, the mixture was filtered through Celite, chloroform was added to the filtrate, the chloroform layer was washed with water, and then dried over magnesium sulfate and further concentrated under reduced pressure to obtain a dark brown oil. This was treated with a silica gel column [eluent: toluene/n-hexane (1:3) mixed solvent], and ethanol/
～、～Recrystallized from dimethylformamide mixed solvent,
Yellow-green needle-shaped crystals were obtained.
この結晶をエタノール中還流撹拌し、濾過をして。The crystals were stirred under reflux in ethanol and filtered.
黄緑色粉末の下式で示されるＮ、〜、Ｎ′、Ｎ′−テト
ラキス（４−メチルフェニル）−１，８−ジアミノピレ
ン（化合物＆２５）０．９２ｇ（収率５１．７％）を得
た。融点は２８０℃以上であった。0.92 g (yield 51.7%) of N, ~, N', N'-tetrakis(4-methylphenyl)-1,8-diaminopyrene (compound &25) represented by the following formula as a yellow-green powder was obtained. Ta. The melting point was 280°C or higher.
ｔｌ、Ｌ
元素分析値はＣ４４Ｈ３，Ｎよとして下記の通Ｃ石
Ｈ％
実測値 ８９．１０ ６．０５
計算値 ８９．１５ ６．１２
りであった。tl, L The elemental analysis value is C44H3,N as shown below.
H% Actual value: 89.10 6.05 Calculated value: 89.15 6.12
Ｎ％
４．６０
４．７３
なお、他のジアミノピレン化合物も前記と同様に合成し
た。N% 4.60 4.73 Other diaminopyrene 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１μ履の電荷発生層
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 resulting dispersion was applied using a doctor blade onto the aluminum surface of a conductive support made of a polyester base coated with aluminum vapor, and air-dried to form a charge generating layer with a thickness of about 1 μm.
一方、電荷搬送物質としては化合物具体例Ｎα４のジア
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Ｘ１３００．■今人製）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２０
μｍの電荷搬送層を形成せしめて感光体Ｎ＋１１を作成
した。On the other hand, as a charge transport substance, 2 parts of a diaminopyrene compound of compound example Nα4, 2 parts of a polycarbonate resin (Panlite Apply on the generation layer using a doctor blade and heat at 80℃.
for 2 minutes, then dried at 120℃ for 5 minutes to a thickness of approximately 20℃.
A photoreceptor N+11 was prepared by forming a charge transport layer of .mu.m.
実施例２〜３３
電荷発生物質および電荷搬送物質（ジアミノピレン化合
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Ｎα２〜３３を作製した。Examples 2 to 33 Photoreceptors Nα2 to 33 were produced in exactly the same manner as in Example 1, except that the charge generating substance and the charge transporting substance (diaminopyrene compound) were replaced with those shown in Table 1.
実施例３４
厚さ約３００μ園のアルミニウム板上にセレンを厚さ約
１μｌに真空蒸着して電荷発生層を形成せしめた。次い
で化合物＆４のジ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４９０
００）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。Example 34 Selenium was vacuum deposited to a thickness of about 1 μl on an aluminum plate having a thickness of about 300 μm to form a charge generation layer. Next, 2 parts of the diaminopyrene compound of Compound &4, polyester resin (Polyester Adhesive 490 manufactured by DuPont)
00) and 45 parts of tetrahydrofuran were mixed and dissolved to prepare a charge transport layer forming liquid, which was applied onto the above charge generation layer (selenium vapor deposited layer) using a doctor blade and air-dried.
減圧下で乾燥して厚さ約１０μ朧の電荷搬送層を形成せ
しめて、本発明の感光体Ｎα３４を得た。A charge transport layer having a thickness of about 10 μm was formed by drying under reduced pressure to obtain a photoreceptor Nα34 of the present invention.
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ジアミノピレン化合物
Ｎｎ４を用いた以外は実施例３４とまったく同様にして
感光体＆３５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 a diaminopyrene compound Nn4 was used as the charge transport material. Photoconductor &35 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、これに化合物＆４のジアミノ
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 the diaminopyrene compound of Compound &4 and a polyester resin were added to the mixture. (Polyester Adhesive 49000 manufactured by DuPont) was added and further mixed to obtain a photosensitive layer forming liquid, which was then applied onto an aluminum-deposited polyester film using a doctor blade, and dried at 100°C for 30 minutes. Thickness approximately 16μm
A photoreceptor Nα36 of the present invention was prepared by forming a photoreceptor layer.
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：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０．５ｊｌＩ５の保護層を形成せしめて感光
体Ｎα３７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 heated to 100°C.
The charge generating layer was dried 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 form a protective layer with a thickness of about 0.5jlI5. A photoreceptor Nα37 was prepared by forming layers.
かくしてつくられた感光体ＮＣＬ１〜３７について、市
販の静電複写紙試験装置（にに川口電機製作所製５Ｐ４
２８型）を用いて一６ＫＶ又は＋６にＶ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
／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。Photoconductors NCL1 to NCL37 thus produced were tested using a commercially available electrostatic copying paper tester (5P4 manufactured by Nini Kawaguchi Electric Seisakusho).
After electrifying the battery by applying a corona discharge of -6 KV or +6 V for 20 seconds using a 28-type battery, it was left in a dark place for 20 seconds, the surface potential Vpo (volts) at that time was measured, and then a tungsten lamp was turned on. , the illuminance of the photoreceptor surface is 4.5
lux so that the surface potential is 1 of Vpo.
/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
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
〔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こ
と、熱や機械的の衝撃に対する強度が大で、しかも安価
に製造することができる。Table 2 [Effects] The photoreceptor of the present invention not only has excellent photosensitive properties, but also has high strength against thermal and mechanical impact, 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。1 to 5 are cross-sectional views enlarged in the thickness direction of an electrophotographic photoreceptor according to the present invention.
Claims (1)
るジ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、Ｒ＾１及びＲ＾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表わし、各々同一でも異なっ
ていてもよい。ただし、１、６−ジアミノピレン化合物
を除く）(1) An electrophotographic photoreceptor comprising, on a conductive support, a photosensitive layer containing as an active ingredient at least one diaminopyrene compound represented by the following general formula (I). ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) (In the formula, R^1 and R^2 represent substituted or unsubstituted alkyl groups or aryl groups, and may be the same or different. However, (excluding 1,6-diaminopyrene compounds)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2175561A JP3030441B2 (en) | 1990-05-30 | 1990-07-02 | Electrophotographic photoreceptor |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14088790 | 1990-05-30 | ||
| JP2-140887 | 1990-05-30 | ||
| JP2175561A JP3030441B2 (en) | 1990-05-30 | 1990-07-02 | Electrophotographic photoreceptor |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH04118658A true JPH04118658A (en) | 1992-04-20 |
| JP3030441B2 JP3030441B2 (en) | 2000-04-10 |
Family
ID=26473268
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2175561A Expired - Fee Related JP3030441B2 (en) | 1990-05-30 | 1990-07-02 | Electrophotographic photoreceptor |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3030441B2 (en) |
Cited By (5)
| 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 |
| JPH1088122A (en) * | 1996-09-12 | 1998-04-07 | Sony Corp | Organic electroluminescent element |
| WO2004083162A1 (en) * | 2003-03-20 | 2004-09-30 | Idemitsu Kosan Co. Ltd. | Aromatic amine derivative and organic electroluminescent element made with the same |
| JP2011154276A (en) * | 2010-01-28 | 2011-08-11 | Ricoh Co Ltd | Electrophotographic photoreceptor, and electrophotographic method, electrophotographic device and process cartridge using the electrophotographic photoreceptor |
| 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
- 1990-07-02 JP JP2175561A patent/JP3030441B2/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 |
| JPH1088122A (en) * | 1996-09-12 | 1998-04-07 | Sony Corp | Organic electroluminescent element |
| WO2004083162A1 (en) * | 2003-03-20 | 2004-09-30 | Idemitsu Kosan Co. Ltd. | Aromatic amine derivative and organic electroluminescent element made with the same |
| EP1604974A1 (en) | 2003-03-20 | 2005-12-14 | 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 |
| 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 |
| JP2011154276A (en) * | 2010-01-28 | 2011-08-11 | Ricoh Co Ltd | Electrophotographic photoreceptor, and electrophotographic method, electrophotographic device and process cartridge using the electrophotographic photoreceptor |
Also Published As
| Publication number | Publication date |
|---|---|
| JP3030441B2 (en) | 2000-04-10 |
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