JPH04288055A - Hydrazone compound and electrophotographic photoreceptor produced by using the same - Google Patents
Hydrazone compound and electrophotographic photoreceptor produced by using the sameInfo
- Publication number
- JPH04288055A JPH04288055A JP5166291A JP5166291A JPH04288055A JP H04288055 A JPH04288055 A JP H04288055A JP 5166291 A JP5166291 A JP 5166291A JP 5166291 A JP5166291 A JP 5166291A JP H04288055 A JPH04288055 A JP H04288055A
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- compound
- compounds
- electrophotographic photoreceptor
- 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.)
- Pending
Links
- -1 Hydrazone compound Chemical class 0.000 title claims abstract description 31
- 108091008695 photoreceptors Proteins 0.000 title claims abstract description 27
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 14
- 125000003118 aryl group Chemical group 0.000 claims abstract description 13
- 239000000758 substrate Substances 0.000 claims abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
- 125000003367 polycyclic group Chemical group 0.000 claims abstract description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 5
- 125000001424 substituent group Chemical group 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 abstract description 36
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract description 10
- 230000035945 sensitivity Effects 0.000 abstract description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract description 6
- 239000002904 solvent Substances 0.000 abstract description 6
- 230000002378 acidificating effect Effects 0.000 abstract description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract description 2
- 230000003068 static effect Effects 0.000 abstract description 2
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- 239000000463 material Substances 0.000 description 45
- 239000010410 layer Substances 0.000 description 35
- 229920005989 resin Polymers 0.000 description 25
- 239000011347 resin Substances 0.000 description 25
- 239000011230 binding agent Substances 0.000 description 16
- 238000000034 method Methods 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000000921 elemental analysis Methods 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 239000002356 single layer Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 3
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- VPUGDVKSAQVFFS-UHFFFAOYSA-N coronene Chemical compound C1=C(C2=C34)C=CC3=CC=C(C=C3)C4=C4C3=CC=C(C=C3)C4=C2C3=C1 VPUGDVKSAQVFFS-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000002739 metals Chemical class 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
- GBROPGWFBFCKAG-UHFFFAOYSA-N picene Chemical compound C1=CC2=C3C=CC=CC3=CC=C2C2=C1C1=CC=CC=C1C=C2 GBROPGWFBFCKAG-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 2
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 2
- 229920005668 polycarbonate resin Polymers 0.000 description 2
- 239000004431 polycarbonate resin Substances 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 229910052711 selenium Inorganic materials 0.000 description 2
- 239000011669 selenium Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 125000000335 thiazolyl group Chemical group 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- YBQZXXMEJHZYMB-UHFFFAOYSA-N 1,2-diphenylhydrazine Chemical compound C=1C=CC=CC=1NNC1=CC=CC=C1 YBQZXXMEJHZYMB-UHFFFAOYSA-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
- JFJWVJAVVIQZRT-UHFFFAOYSA-N 2-phenyl-1,3-dihydropyrazole Chemical class C1C=CNN1C1=CC=CC=C1 JFJWVJAVVIQZRT-UHFFFAOYSA-N 0.000 description 1
- WUPHOULIZUERAE-UHFFFAOYSA-N 3-(oxolan-2-yl)propanoic acid Chemical compound OC(=O)CCC1CCCO1 WUPHOULIZUERAE-UHFFFAOYSA-N 0.000 description 1
- 229910001369 Brass Inorganic materials 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 1
- 239000004709 Chlorinated polyethylene Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000004641 Diallyl-phthalate Substances 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 235000000177 Indigofera tinctoria Nutrition 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical class N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 1
- 229920002433 Vinyl chloride-vinyl acetate copolymer Polymers 0.000 description 1
- QLNFINLXAKOTJB-UHFFFAOYSA-N [As].[Se] Chemical compound [As].[Se] QLNFINLXAKOTJB-UHFFFAOYSA-N 0.000 description 1
- 125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- HXGDTGSAIMULJN-UHFFFAOYSA-N acetnaphthylene Natural products C1=CC(C=C2)=C3C2=CC=CC3=C1 HXGDTGSAIMULJN-UHFFFAOYSA-N 0.000 description 1
- 229920006243 acrylic copolymer Polymers 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910021417 amorphous silicon Inorganic materials 0.000 description 1
- PGEHNUUBUQTUJB-UHFFFAOYSA-N anthanthrone Chemical class C1=CC=C2C(=O)C3=CC=C4C=CC=C5C(=O)C6=CC=C1C2=C6C3=C54 PGEHNUUBUQTUJB-UHFFFAOYSA-N 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
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 1
- 239000010951 brass Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 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
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 229910052980 cadmium sulfide Inorganic materials 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000005038 ethylene vinyl acetate Substances 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 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
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-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
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([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
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 150000002545 isoxazoles Chemical class 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 238000004519 manufacturing process Methods 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
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 125000004572 morpholin-3-yl group Chemical group N1C(COCC1)* 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- NLUKOHAICARXID-UHFFFAOYSA-N n,n-dimethyl-4-(1h-pyrazol-5-yl)aniline Chemical compound C1=CC(N(C)C)=CC=C1C1=CC=NN1 NLUKOHAICARXID-UHFFFAOYSA-N 0.000 description 1
- UDJWHGNSQWLKGR-UHFFFAOYSA-N n-methyl-4-[5-[4-(methylamino)phenyl]-1,3,4-oxadiazol-2-yl]aniline Chemical compound C1=CC(NC)=CC=C1C1=NN=C(C=2C=CC(NC)=CC=2)O1 UDJWHGNSQWLKGR-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 150000002916 oxazoles Chemical class 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- AXFBAIOSECPASO-UHFFFAOYSA-N pentacyclo[6.6.2.02,7.04,16.011,15]hexadeca-1(14),2(7),3,5,8(16),9,11(15),12-octaene Chemical compound C1=C(C=C23)C4=C5C3=CC=CC5=CC=C4C2=C1 AXFBAIOSECPASO-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class 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 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
- 239000004033 plastic Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920002285 poly(styrene-co-acrylonitrile) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- RQGPLDBZHMVWCH-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole Chemical class C1=NC2=CC=NC2=C1 RQGPLDBZHMVWCH-UHFFFAOYSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical class C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- FMKFBRKHHLWKDB-UHFFFAOYSA-N rubicene Chemical compound C12=CC=CC=C2C2=CC=CC3=C2C1=C1C=CC=C2C4=CC=CC=C4C3=C21 FMKFBRKHHLWKDB-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 229960005265 selenium sulfide Drugs 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction 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
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical class C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 150000004961 triphenylmethanes Chemical class 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
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Quinoline Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Photoreceptors In Electrophotography (AREA)
Abstract
Description
【0001】0001
【産業上の利用分野】本発明は、新規なヒドラゾン系化
合物とこれを用いた電子写真感光体に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel hydrazone compound and an electrophotographic photoreceptor using the same.
【0002】0002
【従来の技術】近年、複写機、プリンター、ファクシミ
リ等の画像形成装置における電子写真感光体として、加
工性および経済性にすぐれ、機能設計の自由度が大きい
有機感光体が広く使用されている。また、電子写真感光
体を用いて複写画像を形成する場合には、カールソンプ
ロセスが広く利用されている。カールソンプロセスは、
コロナ放電により感光体を均一に帯電させる帯電工程と
、帯電した感光体に原稿像を露光し原稿像に対応した静
電潜像を形成する露光工程と、静電潜像をトナーを含有
する現像剤で現像しトナー像を形成する現像工程と、ト
ナー像を紙などの基材に転写する転写工程と、基材に転
写されたトナー像を定着させる定着工程と、転写工程後
、感光体上に残留するトナーを除去するクリーニング工
程とを含んでいる。このカールソンプロセスにおいて、
高品質の画像を形成するには、電子写真感光体が帯電特
性および感光特性に優れており、かつ露光後の残留電位
が低いことが要求される。BACKGROUND OF THE INVENTION In recent years, organic photoreceptors have been widely used as electrophotographic photoreceptors in image forming apparatuses such as copying machines, printers, facsimile machines, etc., as they are excellent in processability and economical efficiency and have a large degree of freedom in functional design. Further, when forming a copy image using an electrophotographic photoreceptor, the Carlson process is widely used. The Carlson process is
A charging process in which the photoconductor is uniformly charged by corona discharge, an exposure process in which the charged photoconductor is exposed to an original image to form an electrostatic latent image corresponding to the original image, and the electrostatic latent image is developed using toner. A developing process in which a toner image is formed by developing with a toner image, a transfer process in which the toner image is transferred to a base material such as paper, a fixing process in which the toner image transferred to the base material is fixed, and after the transfer process, a toner image is formed on the photoreceptor. and a cleaning step to remove residual toner. In this Carlson process,
In order to form high-quality images, an electrophotographic photoreceptor is required to have excellent charging characteristics and photosensitive characteristics, and to have a low residual potential after exposure.
【0003】従来より、セレンや硫化カドミウム等の無
機光導電体が電子写真感光体材料として公知であるが、
これらは毒性があり、しかも生産コストが高いという欠
点がある。そこで、これらの無機物質に代えて、種々の
有機物質を用いた、いわゆる有機電子写真感光体が提案
されている。かかる有機電子写真感光体は、露光により
電荷を発生する電荷発生材料と、発生した電荷を輸送す
る機能を有する電荷輸送材料とからなる感光層を有する
。Conventionally, inorganic photoconductors such as selenium and cadmium sulfide have been known as materials for electrophotographic photoreceptors.
These have the disadvantage of being toxic and having high production costs. Therefore, so-called organic electrophotographic photoreceptors using various organic substances in place of these inorganic substances have been proposed. Such an organic electrophotographic photoreceptor has a photosensitive layer composed of a charge-generating material that generates charges upon exposure to light, and a charge-transporting material that has a function of transporting the generated charges.
【0004】かかる有機電子写真感光体に望まれる各種
の条件を満足させるためには、これらの電荷発生材料と
電荷輸送材料との選択を適切に行う必要がある。電荷輸
送材料としては、種々の有機化合物が提案されており、
例えば特開平2−210453号公報には、感度および
帯電能にすぐれ、かつ繰り返し特性にもすぐれた感光体
を提供するべく、電荷輸送材料として下記の一般式で表
されるヒドラゾン系化合物が記載されている。[0004] In order to satisfy various conditions desired for such an organic electrophotographic photoreceptor, it is necessary to appropriately select these charge generating materials and charge transporting materials. Various organic compounds have been proposed as charge transport materials.
For example, JP-A No. 2-210453 describes a hydrazone compound represented by the following general formula as a charge transport material in order to provide a photoreceptor with excellent sensitivity, charging ability, and repeatability. ing.
【0005】[0005]
【化3】[Chemical formula 3]
【0006】(式中、R1 、R2 、Ar1 、Ar
2 、Ar3 、Ar4 およびZは上記公報に記載の
基を示す。)(In the formula, R1, R2, Ar1, Ar
2, Ar3, Ar4 and Z represent the groups described in the above publication. )
【0007】[0007]
【発明が解決しようとする課題】しかしながら、上記公
報に記載のヒドラゾン系化合物を用いた場合、感光層を
構成する結着樹脂との相溶性が低く、かつ導電性基体上
に形成した感光膜の可撓性が悪いという欠点がある。感
光膜の可撓性が悪い場合は、感光体が小径ドラムやベル
トの形態で使用される場合に感光体にクラックが生じた
り、導電性基体から剥落する等のおそれがあり、実用的
ではない。[Problems to be Solved by the Invention] However, when the hydrazone compound described in the above-mentioned publication is used, it has low compatibility with the binder resin constituting the photosensitive layer, and the hydrazone compound described in the above publication has low compatibility with the binder resin constituting the photosensitive layer. It has the disadvantage of poor flexibility. If the photoreceptor film has poor flexibility, it is not practical because there is a risk that the photoreceptor may crack or peel off from the conductive substrate when the photoreceptor is used in the form of a small-diameter drum or belt. .
【0008】本発明の目的は、かかる技術的課題を解決
し、高感度でかつ繰り返し特性に優れる共に、相溶性に
富みかつ可撓性にもすぐれたヒドラゾン系化合物とこれ
を用いた電子写真感光体を提供することである。The purpose of the present invention is to solve the above technical problems and to provide a hydrazone compound which has high sensitivity and excellent repeatability, is highly compatible and has excellent flexibility, and an electrophotographic sensitizer using the same. It's about giving your body.
【0009】[0009]
【課題を解決するための手段および作用】上記の目的を
達成するための本発明のヒドラゾン系化合物は、一般式
(1):[Means and effects for solving the problems] The hydrazone compound of the present invention for achieving the above object has the general formula (1):
【0010】0010
【化4】[C4]
【0011】(式中、R1 およびR2 は同一または
異なって水素原子、アルキル基、アルコキシ基、アリー
ル基またはハロゲン原子を示し、アルキル基、アルコキ
シ基およびアリール基はいずれも置換基を有していても
よい;Ar1 、Ar2 、Ar3 およびAr4 は
同一または異なってアルキル基、アリール基、縮合多環
式基または複素環基を示し、これらの基はいずれも置換
基を有していてもよく、Ar1 とAr2 およびAr
3 とAr4 と はそれぞれ環を形成してもよい;
Xはベンゼン環と共に縮合環を形成する残基を示し、置
換基を有していてもよい;mおよびnは0、1または2
を示す。但し、mおよびnは同時に0でであってはなら
ない。)で表されるものである。(In the formula, R1 and R2 are the same or different and represent a hydrogen atom, an alkyl group, an alkoxy group, an aryl group, or a halogen atom, and each of the alkyl group, alkoxy group, and aryl group has a substituent. Ar1, Ar2, Ar3 and Ar4 are the same or different and represent an alkyl group, an aryl group, a fused polycyclic group, or a heterocyclic group, and any of these groups may have a substituent, and Ar1 and Ar2 and Ar
3 and Ar4 may each form a ring;
X represents a residue that forms a condensed ring with the benzene ring, and may have a substituent; m and n are 0, 1 or 2
shows. However, m and n must not be 0 at the same time. ).
【0012】かかる本発明のヒドラゾン系化合物は電荷
輸送材料、とくにホール輸送材料として有効であり、従
来公知のヒドラゾン系化合物等の電荷輸送材料に比べて
高いホール移動度を有する。さらに、本発明のヒドラゾ
ン系化合物は結着樹脂との相溶性にもすぐれ均一な感光
層を形成できると共に、得られる感光層は可撓性にも富
んでいる。The hydrazone compound of the present invention is effective as a charge transport material, particularly a hole transport material, and has higher hole mobility than conventional charge transport materials such as hydrazone compounds. Further, the hydrazone compound of the present invention has excellent compatibility with the binder resin and can form a uniform photosensitive layer, and the resulting photosensitive layer is also highly flexible.
【0013】従って、本発明の電子写真感光体は、導電
性基体上に、上記一般式(1) で表されるヒドラゾン
系化合物を含有する感光層を設けたことを特徴とし、こ
れにより本発明の電子写真感光体は、可撓性にすぐれて
いるため、小径の感光体ドラムやベルトの形態で使用す
る場合にも感光層にクラックが発生するなどの問題を生
じさせることがなく、しかも感度および帯電能にすぐれ
、高い繰り返し特性を有する。[0013] Therefore, the electrophotographic photoreceptor of the present invention is characterized in that a photosensitive layer containing a hydrazone compound represented by the above general formula (1) is provided on a conductive substrate. The electrophotographic photoreceptor has excellent flexibility, so even when used in the form of a small-diameter photoreceptor drum or belt, it does not cause problems such as cracks in the photoreceptor layer, and has a high sensitivity. It has excellent charging ability and high repeatability.
【0014】前記アルキル基としては、例えばメチル基
、エチル基、プロピル基、イソプロピル基、ブチル基、
イソブチル基、t−ブチル基、ペンチル基、ヘキシル基
などがあげられる。アリール基としては、例えばフェニ
ル基、ナフチル基、ビフェニリル基、アントリル基、フ
ェナントリル基などがあげられる。Examples of the alkyl group include methyl group, ethyl group, propyl group, isopropyl group, butyl group,
Examples include isobutyl group, t-butyl group, pentyl group, and hexyl group. Examples of the aryl group include phenyl group, naphthyl group, biphenylyl group, anthryl group, and phenanthryl group.
【0015】アルコキシ基としては、例えばメトキシ基
、エトキシ基、イソプロポキシ基、ブトキシ基、t−ブ
トキシ基、ヘキシルオキシ基などがあげられる。ハロゲ
ン原子としては、塩素、ヨウ素、臭素、フッ素があげら
れる。縮合多環式基としては、種々の縮合多環式化合物
、例えばトリフェニレン、ピレン、クリセン、ナフタセ
ン、ピセン、ペリレン、ベンゾ〔α〕ピレン、ルビセン
、コロネン、オバレン等の残基があげられる。Examples of the alkoxy group include methoxy group, ethoxy group, isopropoxy group, butoxy group, t-butoxy group, and hexyloxy group. Examples of halogen atoms include chlorine, iodine, bromine, and fluorine. Examples of the fused polycyclic group include residues of various fused polycyclic compounds, such as triphenylene, pyrene, chrysene, naphthacene, picene, perylene, benzo[α]pyrene, rubicene, coronene, obalene, and the like.
【0016】複素環式基としては、例えばチエニル基、
ピロリル基、ピロリジニル基、オキサゾリル基、イソオ
キサゾリル基、チアゾリル基、イソチアゾリル基、イミ
ダゾリル基、2H−イミダゾリル基、ピラゾリル基、ト
リアゾリル基、テトラゾリル基、ピラニル基、ピリジル
基、ピベリジル基、ピペリジノ基、3−モルホリニル基
、モルホリノ基、チアゾリル基などがあげられる。Examples of the heterocyclic group include thienyl group,
Pyrrolyl group, pyrrolidinyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, imidazolyl group, 2H-imidazolyl group, pyrazolyl group, triazolyl group, tetrazolyl group, pyranyl group, pyridyl group, piveridyl group, piperidino group, 3-morpholinyl group group, morpholino group, thiazolyl group, etc.
【0017】また、上記基に置換してもよい置換基とし
ては、例えばハロゲン原子、アルキル等の置換基を有す
ることのあるアミノ基、水酸基、エステル化されていて
もよいカルボキシル基、シアノ基、C1 −C6 アル
キル基、C1 −C6 アルコキシ基、アリール基を有
することのあるC2 −C6 アルケニル基などがあげ
られる。置換基は2以上であってもよく、また2つの置
換基が環を形成していてもよい。Examples of substituents that may be substituted on the above groups include halogen atoms, amino groups that may have substituents such as alkyl, hydroxyl groups, carboxyl groups that may be esterified, cyano groups, Examples thereof include a C1-C6 alkyl group, a C1-C6 alkoxy group, and a C2-C6 alkenyl group that may have an aryl group. There may be two or more substituents, and two substituents may form a ring.
【0018】また、Ar1 とAr2 および/または
Ar3 とAr4 とは一体となって環を形成してもよ
く、このような環としては例えばカルバゾールがあげら
れる。ベンゼン環と共に縮合環を形成する残基を示し置
換基を有していてもよい基:Xとしては、例えばベンゼ
ン環と共にカルバゾリル基、インドリル基、キノリル基
などを形成する炭素数が2〜3の飽和または不飽和な炭
化水素基(エチレン基、プロピレン基、ビニル基等)が
あげられる。Further, Ar1 and Ar2 and/or Ar3 and Ar4 may be combined to form a ring, and examples of such a ring include carbazole. A group that indicates a residue that forms a condensed ring with a benzene ring and may have a substituent: X is, for example, a group having 2 to 3 carbon atoms that forms a carbazolyl group, indolyl group, quinolyl group, etc. with a benzene ring. Examples include saturated or unsaturated hydrocarbon groups (ethylene group, propylene group, vinyl group, etc.).
【0019】前記一般式で表されるヒドラゾン化合物の
具体的化合物としては、以下のものを例示することがで
きる。Specific examples of the hydrazone compound represented by the above general formula include the following.
【0020】[0020]
【化5】[C5]
【0021】[0021]
【化6】[C6]
【0022】[0022]
【化7】[C7]
【0023】前記一般式(1) で表される化合物は、
例えば下記反応式にて製造することができる。
反応式:The compound represented by the general formula (1) is:
For example, it can be produced using the following reaction formula. Reaction formula:
【0024】[0024]
【化8】[Chemical formula 8]
【0025】(式中、R1 、R2 、Ar1 、Ar
2 、Ar3 、Ar4 およびXは前記と同じ、R3
はアルキル基である。)すなわち、式(a) で表さ
れるアルデヒド化合物に対して式(b) で表される化
合物を塩基(水酸化ナトリウム、水酸化カリウム等)の
存在下で反応させて、式(c) で表される中間体を得
る。反応は溶剤中にて温度10〜80℃にて行われる。
溶剤としては、例えばジメチルホルムアミド、ジメチル
スルホキシド等が使用可能である。ついで、この中間体
化合物(c) に式(d) で表されるヒドラジン系化
合物を、酢酸等を加えた酸性条件下で反応させ、本発明
の化合物(1) を得る。この反応は、室温〜80℃の
温度で上記と同様な溶媒中で反応させることができる。(In the formula, R1, R2, Ar1, Ar
2, Ar3, Ar4 and X are the same as above, R3
is an alkyl group. ) That is, by reacting an aldehyde compound represented by formula (a) with a compound represented by formula (b) in the presence of a base (sodium hydroxide, potassium hydroxide, etc.), formula (c) is obtained. The intermediate represented is obtained. The reaction is carried out in a solvent at a temperature of 10-80°C. As the solvent, for example, dimethylformamide, dimethyl sulfoxide, etc. can be used. Then, this intermediate compound (c) is reacted with a hydrazine compound represented by the formula (d) under acidic conditions with the addition of acetic acid or the like to obtain the compound (1) of the present invention. This reaction can be carried out in the same solvent as above at a temperature of room temperature to 80°C.
【0026】本発明における感光層は、前記一般式(1
) で表される化合物の1種または2種以上を含有する
。本発明における感光層には、電荷発生材料、電荷輸送
材料である前記一般式(1) で表される化合物および
結着樹脂を混合した単層型と、電荷発生層および電荷輸
送層を積層した積層型とがあるが、本発明の感光層はい
ずれにも適用可能である。The photosensitive layer in the present invention has the general formula (1
) Contains one or more compounds represented by: The photosensitive layer in the present invention includes a single-layer type in which a charge-generating material, a charge-transporting material, which is a compound represented by the general formula (1) and a binder resin, and a charge-generating layer and a charge-transporting layer are laminated. Although there is a laminated type, the photosensitive layer of the present invention can be applied to either type.
【0027】積層型の電子写真感光体を得るには、導電
性基材上に電荷発生材料を含有する電荷発生層を形成し
、この電荷発生層上に、電荷輸送材料である前記一般式
で表される化合物を含有する電荷輸送層を形成すればよ
い。また、積層順序をこれと逆にし、電荷輸送層上に電
荷発生層を設けるようにしてもよい。電荷発生材料とし
ては、従来より使用されているセレン、セレン−テルル
、セレン−ヒ素、アモルファスシリコン、ピリリウム塩
、アゾ系化合物、ジスアゾ系化合物、フタロシアニン系
化合物、アンサンスロン系化合物、ペリレン系化合物、
インジゴ系化合物、トリフェニルメタン系化合物、スレ
ン系化合物、トルイジン系化合物、ピラゾリン系化合物
、ペリレン系化合物、キナクリドン系化合物、ピロロピ
ロール系化合物等があげられる。これらの電荷発生材料
は1種または2種以上を混合して使用することができる
。In order to obtain a laminated type electrophotographic photoreceptor, a charge generation layer containing a charge generation material is formed on a conductive base material, and a charge transport material having the above general formula is formed on this charge generation layer. A charge transport layer containing the represented compound may be formed. Furthermore, the stacking order may be reversed and the charge generation layer may be provided on the charge transport layer. As charge generating materials, conventionally used selenium, selenium-tellurium, selenium-arsenic, amorphous silicon, pyrylium salts, azo compounds, disazo compounds, phthalocyanine compounds, anthanthrone compounds, perylene compounds,
Examples include indigo compounds, triphenylmethane compounds, threne compounds, toluidine compounds, pyrazoline compounds, perylene compounds, quinacridone compounds, and pyrrolopyrrole compounds. These charge generating materials can be used alone or in combination of two or more.
【0028】また、電荷輸送材料である前記一般式で表
される化合物は、従来公知の他の電荷輸送材料と組み合
わせて使用することができる。従来公知の電荷輸送材料
としては、例えば2,5−ジ(4−メチルアミノフェニ
ル)−1,3,4−オキサジアゾールなどのオキサジア
ゾール系化合物、9−(4−ジエチルアミノスチリル)
アントラセン等のスチリル系化合物、ポリビニルカルバ
ゾール等のカルバゾール系化合物、1−フェニル−3−
(p−ジメチルアミノフェニル)ピラゾール等のピラゾ
リン系化合物、トリフェニルアミン系化合物、インドー
ル系化合物、オキサゾール系化合物、イソオキサゾール
系化合物、チアゾール系化合物、チアジアゾール系化合
物、イミダゾール系化合物、ピラゾール系化合物、トリ
アゾール系化合物等の含窒素環式化合物、縮合多環式化
合物が例示される。なお、ポリビニルカルバゾール等の
成膜性を有する電荷輸送材料を使用する場合には結着樹
脂は必ずしも必要ではない。[0028] Furthermore, the compound represented by the above general formula, which is a charge transporting material, can be used in combination with other conventionally known charge transporting materials. Conventionally known charge transport materials include, for example, oxadiazole compounds such as 2,5-di(4-methylaminophenyl)-1,3,4-oxadiazole, and 9-(4-diethylaminostyryl).
Styryl compounds such as anthracene, carbazole compounds such as polyvinylcarbazole, 1-phenyl-3-
Pyrazoline compounds such as (p-dimethylaminophenyl) pyrazole, triphenylamine compounds, indole compounds, oxazole compounds, isoxazole compounds, thiazole compounds, thiadiazole compounds, imidazole compounds, pyrazole compounds, triazoles Examples include nitrogen-containing cyclic compounds such as system compounds, and fused polycyclic compounds. Note that a binder resin is not necessarily required when a charge transporting material having film-forming properties such as polyvinylcarbazole is used.
【0029】前記結着樹脂としては、種々の樹脂が使用
可能であり、例えばスチレン系重合体、スチレン−ブタ
ジエン共重合体、スチレン−アクリロニトリル共重合体
、スチレン−マレイン酸共重合体、アクリル共重合体、
スチレン−アクリル酸共重合体、ポリエチレン、エチレ
ン−酢酸ビニル共重合体、塩素化ポリエチレン、ポリ塩
化ビニル、ポリプロピレン、塩化ビニル−酢酸ビニル共
重合体、ポリエステル、アルキド樹脂、ポリアミド、ポ
リウレタン、ポリカーボネート、ポリアリレート、ポリ
スルホン、ジアリルフタレート樹脂、ケトン樹脂、ホリ
ビニルブチラール樹脂、ポリエーテル樹脂等の熱可塑性
樹脂や、シリコーン樹脂、エポキシ樹脂、その他架橋性
の熱硬化性樹脂、さらにエポキシアクリレート、ウレタ
ン−アクリレートなどの光硬化性樹脂などがあげられる
。これらの結着樹脂は1種または2種以上を混合して用
いることができる。Various resins can be used as the binder resin, such as styrene polymers, styrene-butadiene copolymers, styrene-acrylonitrile copolymers, styrene-maleic acid copolymers, and acrylic copolymers. Union,
Styrene-acrylic acid copolymer, polyethylene, ethylene-vinyl acetate copolymer, chlorinated polyethylene, polyvinyl chloride, polypropylene, vinyl chloride-vinyl acetate copolymer, polyester, alkyd resin, polyamide, polyurethane, polycarbonate, polyarylate , thermoplastic resins such as polysulfone, diallyl phthalate resin, ketone resin, polyvinyl butyral resin, polyether resin, silicone resin, epoxy resin, and other crosslinkable thermosetting resins, as well as photosensitive resins such as epoxy acrylate and urethane-acrylate. Examples include curable resins. These binder resins can be used alone or in combination of two or more.
【0030】また、電荷発生材料、電荷輸送材料および
結着樹脂を溶解して塗布液をつくるための溶剤としては
、例えばメタノール、エタノール、イソプロパノール、
ブタノール等のアルコール類、n−ヘキサン、オクタン
、シクロヘキサン等の脂肪族系炭化水素、ベンゼン、ト
ルエン、キシレン等の芳香族炭化水素、ジクロロメタン
、ジクロロエタン、四塩化炭素、クロロベンゼン等のハ
ロゲン化炭化水素、ジメチルエーテル、ジエチルエーテ
ル、テトラヒドロフラン、エチレングリコールジメチル
エーテル、ジエチレングリコールジメチルエーテル等の
エーテル類、アセトン、メチルエチルケトン、シクロヘ
キサノン等のケトン類、酢酸エチル、酢酸メチル等のエ
ステル類、ジメチルホルムアルデヒド、ジメチルホルム
アミド、ジメチルスルホキシド等があげられる。
これらの溶剤は1種または2種以上を混合して用いるこ
とができる。[0030] Examples of the solvent for dissolving the charge generating material, charge transporting material and binder resin to prepare a coating solution include methanol, ethanol, isopropanol,
Alcohols such as butanol, aliphatic hydrocarbons such as n-hexane, octane, and cyclohexane, aromatic hydrocarbons such as benzene, toluene, and xylene, halogenated hydrocarbons such as dichloromethane, dichloroethane, carbon tetrachloride, and chlorobenzene, and dimethyl ether. , ethers such as diethyl ether, tetrahydrofuran, ethylene glycol dimethyl ether, and diethylene glycol dimethyl ether, ketones such as acetone, methyl ethyl ketone, and cyclohexanone, esters such as ethyl acetate and methyl acetate, dimethyl formaldehyde, dimethyl formamide, and dimethyl sulfoxide. These solvents can be used alone or in combination of two or more.
【0031】また、電荷発生層の感度を向上させるため
に、例えばターフェニル、ハロナフトキノン類、アセナ
フチレン等の公知の増感剤を上記電荷発生材料と共に使
用してもよい。さらに、電荷輸送材料や電荷発生材料の
分散性、染工性等をよくするために界面活性剤、レベリ
ング剤等を使用してもよい。上記導電性基体としては、
例えばアルミニウム、銅、スズ、白金、銀、バナジウム
、モリブデン、クロム、カドミウム、チタン、ニッケル
、パラジウム、インジウム、ステンレス鋼、真鍮等の金
属単体や、上記金属が蒸着またはラミネートされたプラ
スチック材料、ヨウ化アルミニウム、酸化スズ、酸化イ
ンジウム等で被覆されたガラス等が例示される。Further, in order to improve the sensitivity of the charge generation layer, a known sensitizer such as terphenyl, halonaphthoquinones, acenaphthylene, etc. may be used together with the above charge generation material. Furthermore, a surfactant, a leveling agent, etc. may be used to improve the dispersibility, dyeability, etc. of the charge transport material and charge generation material. As the conductive substrate,
For example, single metals such as aluminum, copper, tin, platinum, silver, vanadium, molybdenum, chromium, cadmium, titanium, nickel, palladium, indium, stainless steel, brass, plastic materials on which the above metals are vapor-deposited or laminated, and iodide. Examples include glass coated with aluminum, tin oxide, indium oxide, etc.
【0032】導電性基体はシート状、ドラム状などのい
ずれであってもよく、基体自体が導電性を有するか、あ
るいは基体の表面が導電性を有していればよい。また、
基体は、使用に際して、充分な機械的強度を有するもの
が好ましい。積層型電子写真感光体において、電荷発生
層を構成する電荷発生材料と結着樹脂とは種々の割合で
使用することができるが、結着樹脂100部(重量部、
以下同じ)に対して、電荷発生材料5〜500部、とく
に10〜250部の割合で用いるのが好ましい。The conductive substrate may be in the form of a sheet or a drum, as long as the substrate itself is conductive or the surface of the substrate is conductive. Also,
The substrate preferably has sufficient mechanical strength during use. In the laminated electrophotographic photoreceptor, the charge generation material and the binder resin constituting the charge generation layer can be used in various ratios, but 100 parts of the binder resin (parts by weight,
It is preferable to use 5 to 500 parts, particularly 10 to 250 parts, of the charge generating material (the same applies hereinafter).
【0033】また、電荷発生層は、適宜の膜厚を有して
いてもよいが、0.01〜5μm、とくに0.1〜3μ
m程度に形成されるのが好ましい。電荷輸送層を構成す
る上記一般式(1) で表される化合物(電荷輸送材料
)と前記結着樹脂とは種々の割合で使用することができ
るが、光照射により電荷発生層で生じた電荷が容易に輸
送できるように、結着樹脂100部に対して、上記一般
式で表される化合物を10〜500部、とくに25〜2
00部の割合で用いるのが好ましい。[0033] The charge generation layer may have an appropriate thickness, but it may have a thickness of 0.01 to 5 μm, particularly 0.1 to 3 μm.
It is preferable that the diameter is about m. The compound represented by the above general formula (1) (charge transport material) constituting the charge transport layer and the binder resin can be used in various ratios, but the charge generated in the charge generation layer by light irradiation can be 10 to 500 parts, especially 25 to 2 parts, of the compound represented by the above general formula is added to 100 parts of the binder resin so that it can be easily transported.
Preferably, it is used in a proportion of 0.00 parts.
【0034】また、電荷輸送層は、2〜100μm、と
くに5〜30μm程度に形成されるのが好ましい。単層
型の電子写真感光体においては、結着樹脂100部に対
して電荷発生材料は2〜20部、とくに3〜15部、上
記一般式で表される化合物(電荷輸送材料)は40〜2
00部、とくに50〜150部であるのが適当である。
また、単層型の感光層の厚さは10〜50μm、とくに
15〜30μm程度であるのが好ましい。Further, the charge transport layer is preferably formed to have a thickness of about 2 to 100 μm, particularly about 5 to 30 μm. In a single-layer type electrophotographic photoreceptor, the amount of the charge generating material is 2 to 20 parts, especially 3 to 15 parts, and the amount of the compound represented by the above general formula (charge transporting material) is 40 to 40 parts per 100 parts of the binder resin. 2
00 parts, especially 50 to 150 parts is suitable. Further, the thickness of the single-layer type photosensitive layer is preferably about 10 to 50 μm, particularly about 15 to 30 μm.
【0035】電荷発生層および電荷輸送層を含む感光層
を塗布手段により形成する場合には、電荷発生材料また
は電荷輸送材料と結着樹脂とを、従来公知の方法、例え
ばロールミル、ボールミル、アトライタ、ペイントシェ
ーカー、超音波分散器等を用いて塗布液を調製する。When a photosensitive layer including a charge generating layer and a charge transporting layer is formed by a coating method, the charge generating material or the charge transporting material and the binder resin are coated by a conventionally known method such as a roll mill, a ball mill, an attritor, or a binder resin. Prepare the coating solution using a paint shaker, ultrasonic disperser, etc.
【0036】[0036]
【実施例】以下、実施例および比較例をあげて本発明を
詳細に説明する。
実施例1
<上記式(5) で表される化合物の合成>下記式(1
7)で表されるアルデヒド化合物27.7gに対して、
下記式(18)で表される化合物27.1gを水酸化ナ
トリウムの存在下、ジメチルホルムアミド中にて50℃
で4時間反応させた。[Examples] The present invention will be explained in detail below with reference to Examples and Comparative Examples. Example 1 <Synthesis of the compound represented by the above formula (5)> The following formula (1
For 27.7 g of the aldehyde compound represented by 7),
27.1 g of the compound represented by the following formula (18) was heated at 50°C in dimethylformamide in the presence of sodium hydroxide.
The mixture was allowed to react for 4 hours.
【0037】[0037]
【化9】[Chemical formula 9]
【0038】生成物を常法により単離・精製したのち、
ジフェニルヒドラジン(C6 H5)2 N−NH2
の10gと酸性下、エチルアルコール中にて室温で攪拌
しながら反応させ、上式(5) で表される化合物を得
た。
元素分析値:C45H40N4 として計算値(%)
C84.87 H6.33 N8.80実
測値(%) C85.01 H6.30
N8.69適当な出発原料を用いて実施例1と同様にし
て各化合物を製造した。得られた各化合物は以下のとお
りである。
実施例2
<式(6) で表される化合物>
元素分析値:C46H41N3 として計算値(%)
C86.89 H6.50 N6.61実
測値(%) C86.79 H6.52
N6.69実施例3
<式(8) で表される化合物>
元素分析値:C49H39N3 として計算値(%)
C88.17 H6.20 N6.63実
測値(%) C88.06 H6.25
N6.69実施例4
<式(9) で表される化合物>
元素分析値:C51H31N3 として計算値(%)
C88.79 H5.11 N6.09実
測値(%) C88.85 H5.07
N6.06実施例5
<式(10)で表される化合物>
元素分析値:C48H40N3 として計算値(%)
C87.90 H5.69 N6.41実
測値(%) C87.98 H5.67
N6.35実施例6
<式(11)で表される化合物>
元素分析値:C43H35N3 として計算値(%)
C86.98 H5.94 N7.08実
測値(%) C87.07 H5.90
N7.03実施例7
<式(15)で表される化合物>
元素分析値:C51H41N3 O2 として計算値(
%) C84.15 H5.68 N5.
77実測値(%) C84.09 H5.71
N5.80実施例8
<式(16)で表される化合物>
元素分析値:C50H39N3 として計算値(%)
C88.07 H5.77 N6.16実
測値(%) C88.05 H5.72
N6.23実施例9〜13および比較例1,2(積層型
感光層)電荷発生材料2部、ポリビニルブチラール樹脂
(積水化学工業社製の「S−lecBM−5)」1部、
テトラヒドロフラン120部を、ジルコニアビーズ(2
mm径) を用いたペイントシェーカーにて2 時間分
散させた。得られた分散液をアルミニウムシート上にワ
イヤーバーを用いて塗工し、100℃で1時間乾燥し、
0.5μmの電荷発生層を得た。使用した電荷発生材料
は表1および表2に示した。これらの表において、電荷
発生材料A,BおよびCはそれぞれ下記式(A),(B
)および(C)で表される化合物を意味している。After the product is isolated and purified by conventional methods,
Diphenylhydrazine (C6 H5)2 N-NH2
The compound was reacted with 10 g of the above compound in ethyl alcohol under acidic conditions at room temperature with stirring to obtain a compound represented by the above formula (5). Elemental analysis value: Calculated value (%) as C45H40N4
C84.87 H6.33 N8.80 actual value (%) C85.01 H6.30
N8.69 Each compound was produced in the same manner as in Example 1 using appropriate starting materials. The obtained compounds are as follows. Example 2 <Compound represented by formula (6)> Elemental analysis value: Calculated value (%) as C46H41N3
C86.89 H6.50 N6.61 actual value (%) C86.79 H6.52
N6.69 Example 3 <Compound represented by formula (8)> Elemental analysis value: Calculated value (%) as C49H39N3
C88.17 H6.20 N6.63 actual value (%) C88.06 H6.25
N6.69 Example 4 <Compound represented by formula (9)> Elemental analysis value: Calculated value (%) as C51H31N3
C88.79 H5.11 N6.09 actual value (%) C88.85 H5.07
N6.06 Example 5 <Compound represented by formula (10)> Elemental analysis value: Calculated value (%) as C48H40N3
C87.90 H5.69 N6.41 actual value (%) C87.98 H5.67
N6.35 Example 6 <Compound represented by formula (11)> Elemental analysis value: Calculated value (%) as C43H35N3
C86.98 H5.94 N7.08 actual value (%) C87.07 H5.90
N7.03 Example 7 <Compound represented by formula (15)> Elemental analysis value: Calculated value as C51H41N3 O2 (
%) C84.15 H5.68 N5.
77 Actual value (%) C84.09 H5.71
N5.80 Example 8 <Compound represented by formula (16)> Elemental analysis value: Calculated value (%) as C50H39N3
C88.07 H5.77 N6.16 actual value (%) C88.05 H5.72
N6.23 Examples 9 to 13 and Comparative Examples 1 and 2 (laminated photosensitive layer) 2 parts of charge generating material, 1 part of polyvinyl butyral resin ("S-lecBM-5" manufactured by Sekisui Chemical Co., Ltd.),
120 parts of tetrahydrofuran was mixed with zirconia beads (2
The mixture was dispersed for 2 hours using a paint shaker (mm diameter). The resulting dispersion was applied onto an aluminum sheet using a wire bar, dried at 100°C for 1 hour,
A charge generation layer of 0.5 μm was obtained. The charge generating materials used are shown in Tables 1 and 2. In these tables, charge generating materials A, B and C have the following formulas (A) and (B
) and (C).
【0039】[0039]
【化10】[Chemical formula 10]
【0040】この電荷発生層上に電荷輸送材料1部、ポ
リカーボネート樹脂(三菱瓦斯化学社製の「Z−300
」)1部をトルエン9部に溶解した溶液をワイヤーバー
にて塗工し、100℃で1時間乾燥し、22μmの電荷
輸送層を得た。実施例9〜13で使用した電荷輸送材料
は、表1および表2において前述の具体例で示した化合
物の番号で示した。また、比較例1〜2で使用した電荷
輸送材料I〜IIはそれぞれ下記式(I)〜(II)で
表される化合物を意味している。[0040] On this charge generation layer, 1 part of a charge transport material and a polycarbonate resin ("Z-300" manufactured by Mitsubishi Gas Chemical Co., Ltd.
A solution prepared by dissolving 1 part of '') in 9 parts of toluene was applied using a wire bar and dried at 100°C for 1 hour to obtain a charge transport layer of 22 μm. The charge transport materials used in Examples 9 to 13 are shown in Tables 1 and 2 by the compound numbers shown in the specific examples above. Further, charge transport materials I and II used in Comparative Examples 1 and 2 refer to compounds represented by the following formulas (I) to (II), respectively.
【0041】[0041]
【化11】[Chemical formula 11]
【0042】実施例14〜16および比較例3,4(単
層型感光層)
電荷発生剤1部およびテトラヒドロフラン60部を、ジ
ルコニアビーズ(2mm径) を用いたペイントシェー
カーにて2 時間分散させた。得られた分散液に、固形
分が20重量%のポリカーボネート樹脂(三菱瓦斯化学
社製の「Z−300」)のテトラヒドロフラン溶液50
部および電荷輸送材料10部を加え、さらに1時間分散
を続けた。得られた分散液をアルミニウムシート上にワ
イヤーバーを用いて塗工し、100℃で1時間乾燥し、
20μmの感光層を得た。使用した電荷発生材料および
電荷輸送材料は、表1および表2において、前記実施例
と同様にそれぞれの化学構造式に付した番号で表した。Examples 14 to 16 and Comparative Examples 3 and 4 (single-layer photosensitive layer) 1 part of a charge generating agent and 60 parts of tetrahydrofuran were dispersed for 2 hours in a paint shaker using zirconia beads (2 mm diameter). . 50% of a tetrahydrofuran solution of polycarbonate resin ("Z-300" manufactured by Mitsubishi Gas Chemical Co., Ltd.) with a solid content of 20% by weight was added to the obtained dispersion.
1 part and 10 parts of charge transport material were added and dispersion continued for an additional hour. The resulting dispersion was applied onto an aluminum sheet using a wire bar, dried at 100°C for 1 hour,
A 20 μm photosensitive layer was obtained. The charge generating materials and charge transporting materials used are shown in Tables 1 and 2 by numbers attached to their respective chemical structural formulas, as in the above examples.
【0043】(評価試験)各実施例および比較例で得た
感光体の表面電位、半減露光量(E1/2 )および残
留電位を評価試験機(川口電気社製の「EPA8100
」)にて測定した。測定条件は以下の通りである。
光強度:50ルクス
露光強度:1/15秒
表面電位:(±)700V付近となるように流れ込み電
流値を調整した。(Evaluation test) The surface potential, half-decreased exposure (E1/2) and residual potential of the photoreceptor obtained in each example and comparative example were measured using an evaluation tester ("EPA8100" manufactured by Kawaguchi Electric Co., Ltd.).
”). The measurement conditions are as follows. Light intensity: 50 lux Exposure intensity: 1/15 seconds Surface potential: The inflow current value was adjusted so as to be around (±)700V.
【0044】光源:タングステンランプ除電:200ル
クス
残留電位測定:露光開始後0.2秒後に測定開始した。
実施例9〜16の試験結果を表1に、比較例1〜4の試
験結果を表2にそれぞれ示す。Light source: Tungsten lamp Static elimination: 200 lux Residual potential measurement: Measurement was started 0.2 seconds after the start of exposure. The test results of Examples 9 to 16 are shown in Table 1, and the test results of Comparative Examples 1 to 4 are shown in Table 2.
【0045】[0045]
【表1】[Table 1]
【0046】[0046]
【表2】[Table 2]
【0047】これらの試験結果から、各実施例の感光層
は表面電位については、従来の感光体(比較例)とほと
んど差はない反面、半減露光量および残留電位において
すぐれており、感度が著しく改善されていることがわか
る。From these test results, the photosensitive layers of each example showed almost no difference in surface potential from the conventional photoconductor (comparative example), but were superior in half-life exposure and residual potential, and the sensitivity was significantly lower. You can see that it has been improved.
【0048】[0048]
【発明の効果】以上のように本発明のヒドラゾン系化合
物を用いた電子写真感光体は、帯電能および感度にすぐ
れているほか、ヒドラゾン系化合物が結着樹脂との相溶
性にも富んでいるため、均一な感光層を得ることができ
、さらに可撓性にも富んでいるという効果がある。[Effects of the Invention] As described above, the electrophotographic photoreceptor using the hydrazone compound of the present invention has excellent charging ability and sensitivity, and the hydrazone compound also has high compatibility with the binder resin. Therefore, it is possible to obtain a uniform photosensitive layer, and it also has the advantage of being highly flexible.
Claims (2)
原子、アルキル基、アルコキシ基、アリール基またはハ
ロゲン原子を示し、アルキル基、アルコキシ基およびア
リール基はいずれも置換基を有していてもよい;Ar1
、Ar2 、Ar3 およびAr4 は同一または異
なってアルキル基、アリール基、縮合多環式基または複
素環基を示し、これらの基はいずれも置換基を有してい
てもよく、Ar1 とAr2 およびAr3 とAr4
とはそれぞれ環を形成してもよい;Xはベンゼン環と
共に縮合環を形成する残基を示し、置換基を有していて
もよい;mおよびnは0、1または2を示す。但し、m
およびnは同時に0であってはならない。)で表される
ヒドラゾン系化合物。Claim 1: General formula (1): [Formula 1] (wherein R1 and R2 are the same or different and represent a hydrogen atom, an alkyl group, an alkoxy group, an aryl group, or a halogen atom; Any of the aryl groups may have a substituent; Ar1
, Ar2, Ar3 and Ar4 are the same or different and represent an alkyl group, an aryl group, a fused polycyclic group or a heterocyclic group, and any of these groups may have a substituent, and Ar1, Ar2 and Ar3 and Ar4
may each form a ring; X represents a residue that forms a condensed ring with the benzene ring, and may have a substituent; m and n represent 0, 1 or 2; However, m
and n must not be 0 at the same time. ) A hydrazone compound represented by
されるヒドラゾン系化合物を含有する感光層を設けたこ
とを特徴とする電子写真感光体。 【化2】 (式中、R1 およびR2 は同一または異なって水素
原子、アルキル基、アルコキシ基、アリール基またはハ
ロゲン原子を示し、アルキル基、アルコキシ基およびア
リール基はいずれも置換基を有していてもよい;Ar1
、Ar2 、Ar3 およびAr4 は同一または異
なってアルキル基、アリール基、縮合多環式基または複
素環基を示し、これらの基はいずれも置換基を有してい
てもよく、Ar1 とAr2 およびAr3 とAr4
とはそれぞれ環を形成してもよい;Xはベンゼン環と
共に縮合環を形成する残基を示し、置換基を有していて
もよい;mおよびnは0または1を示す。但し、mおよ
びnは同時に0でであってはならない。)2. An electrophotographic photoreceptor characterized in that a photosensitive layer containing a hydrazone compound represented by the following general formula (1) is provided on a conductive substrate. [Formula 2] (In the formula, R1 and R2 are the same or different and represent a hydrogen atom, an alkyl group, an alkoxy group, an aryl group, or a halogen atom, and each of the alkyl group, alkoxy group, and aryl group has a substituent. May be; Ar1
, Ar2, Ar3 and Ar4 are the same or different and represent an alkyl group, an aryl group, a fused polycyclic group or a heterocyclic group, and any of these groups may have a substituent, and Ar1, Ar2 and Ar3 and Ar4
may each form a ring; X represents a residue that forms a condensed ring with the benzene ring, and may have a substituent; m and n represent 0 or 1; However, m and n must not be 0 at the same time. )
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP5166291A JPH04288055A (en) | 1991-03-15 | 1991-03-15 | Hydrazone compound and electrophotographic photoreceptor produced by using the same |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP5166291A JPH04288055A (en) | 1991-03-15 | 1991-03-15 | Hydrazone compound and electrophotographic photoreceptor produced by using the same |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH04288055A true JPH04288055A (en) | 1992-10-13 |
Family
ID=12893092
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP5166291A Pending JPH04288055A (en) | 1991-03-15 | 1991-03-15 | Hydrazone compound and electrophotographic photoreceptor produced by using the same |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH04288055A (en) |
-
1991
- 1991-03-15 JP JP5166291A patent/JPH04288055A/en active Pending
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