JPS63116157A - Electrophotographic sensitive body - Google Patents
Electrophotographic sensitive bodyInfo
- Publication number
- JPS63116157A JPS63116157A JP26202986A JP26202986A JPS63116157A JP S63116157 A JPS63116157 A JP S63116157A JP 26202986 A JP26202986 A JP 26202986A JP 26202986 A JP26202986 A JP 26202986A JP S63116157 A JPS63116157 A JP S63116157A
- Authority
- JP
- Japan
- Prior art keywords
- general formula
- group
- carrier
- formulas
- tables
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- -1 azo compound Chemical class 0.000 claims abstract description 36
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 4
- 108091008695 photoreceptors Proteins 0.000 claims description 49
- 239000000126 substance Substances 0.000 claims description 39
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 239000010410 layer Substances 0.000 abstract description 35
- 230000035945 sensitivity Effects 0.000 abstract description 14
- 239000000463 material Substances 0.000 abstract description 12
- 239000002356 single layer Substances 0.000 abstract description 4
- 239000000758 substrate Substances 0.000 abstract description 4
- 230000006866 deterioration Effects 0.000 abstract description 3
- 125000000547 substituted alkyl group Chemical group 0.000 abstract description 2
- 150000002431 hydrogen Chemical group 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical group 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 10
- 229920005989 resin Polymers 0.000 description 10
- 239000011347 resin Substances 0.000 description 10
- 239000011230 binding agent Substances 0.000 description 9
- 229910052782 aluminium Inorganic materials 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 229920001225 polyester resin Polymers 0.000 description 4
- 239000004645 polyester resin Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-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
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 3
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 3
- 229910052980 cadmium sulfide Inorganic materials 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 229910052711 selenium Inorganic materials 0.000 description 3
- 239000011669 selenium Substances 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 206010034972 Photosensitivity reaction Diseases 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 229920006026 co-polymeric resin Polymers 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000036211 photosensitivity Effects 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 2
- 229920005668 polycarbonate resin Polymers 0.000 description 2
- 239000004431 polycarbonate resin Substances 0.000 description 2
- 229920005596 polymer binder Polymers 0.000 description 2
- 239000002491 polymer binding agent Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 229920002050 silicone resin Polymers 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 229910001369 Brass Inorganic materials 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000004419 Panlite Substances 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 229920002433 Vinyl chloride-vinyl acetate copolymer Polymers 0.000 description 1
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 description 1
- BNZSIHASOJXAMG-UHFFFAOYSA-N [NH4+].[NH4+].[NH4+].[NH4+].[NH4+].[NH4+].[NH4+].[NH4+].[NH4+].[F-].[F-].[F-].[F-].[F-].[F-].[O-]P([O-])([O-])=O Chemical compound [NH4+].[NH4+].[NH4+].[NH4+].[NH4+].[NH4+].[NH4+].[NH4+].[NH4+].[F-].[F-].[F-].[F-].[F-].[F-].[O-]P([O-])([O-])=O BNZSIHASOJXAMG-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 229920006243 acrylic copolymer Polymers 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000005263 alkylenediamine group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000001454 anthracenes Chemical class 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
- 230000004888 barrier function Effects 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 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
- 239000010951 brass Substances 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
- 239000006229 carbon black Substances 0.000 description 1
- 239000012461 cellulose resin Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000004803 chlorobenzyl group Chemical group 0.000 description 1
- HGAZMNJKRQFZKS-UHFFFAOYSA-N chloroethene;ethenyl acetate Chemical compound ClC=C.CC(=O)OC=C HGAZMNJKRQFZKS-UHFFFAOYSA-N 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 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
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000004802 cyanophenyl group Chemical group 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 125000004188 dichlorophenyl group Chemical group 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 230000005496 eutectics Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- IYWCBYFJFZCCGV-UHFFFAOYSA-N formamide;hydrate Chemical compound O.NC=O IYWCBYFJFZCCGV-UHFFFAOYSA-N 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 238000005286 illumination Methods 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
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 239000005001 laminate film Substances 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000006178 methyl benzyl group Chemical group 0.000 description 1
- KLNUTTQQHSRBIE-UHFFFAOYSA-N n-(2-chlorophenyl)-3-hydroxynaphthalene-2-carboxamide Chemical compound OC1=CC2=CC=CC=C2C=C1C(=O)NC1=CC=CC=C1Cl KLNUTTQQHSRBIE-UHFFFAOYSA-N 0.000 description 1
- FKJARBPQBIATJT-UHFFFAOYSA-N n-benzyl-n-phenylaniline Chemical class C=1C=CC=CC=1CN(C=1C=CC=CC=1)C1=CC=CC=C1 FKJARBPQBIATJT-UHFFFAOYSA-N 0.000 description 1
- GTWJETSWSUWSEJ-UHFFFAOYSA-N n-benzylaniline Chemical class C=1C=CC=CC=1CNC1=CC=CC=C1 GTWJETSWSUWSEJ-UHFFFAOYSA-N 0.000 description 1
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 150000002916 oxazoles Chemical class 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000004076 pyridyl 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
- 230000003252 repetitive effect Effects 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 150000001629 stilbenes Chemical class 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000005628 tolylene group Chemical group 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 125000006617 triphenylamine group 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
- 238000007740 vapor deposition Methods 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 125000006839 xylylene group Chemical group 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
- G03G5/0664—Dyes
- G03G5/0675—Azo dyes
- G03G5/0679—Disazo dyes
- G03G5/0681—Disazo dyes containing hetero rings in the part of the molecule between the azo-groups
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Photoreceptors In Electrophotography (AREA)
Abstract
Description
【発明の詳細な説明】
〔発明の目的〕
（産業上の利用分野）
本発明は電子写真感光体に関するものであり、更に詳し
くは、導電性支持体上にキャリア発生物質として特定の
アゾ化合物を含有せしめることにより。[Detailed Description of the Invention] [Object of the Invention] (Industrial Application Field) The present invention relates to an electrophotographic photoreceptor, and more specifically, the present invention relates to an electrophotographic photoreceptor, and more specifically, a specific azo compound is coated on a conductive support as a carrier generating substance. By making it contain.
優れた光感度、耐久性を有する新規な電子写真感光体を
提供するものである。The present invention provides a novel electrophotographic photoreceptor having excellent photosensitivity and durability.
（従来の技術）
電子写真法は既にカールソンが米国特許第２．２９７．
６９１号に明らかにしたように、この写真法は静電現象
と光導電現象とを巧妙に組合せしたものであり、光導電
性感光体を暗所でコロナ放電等により。(Prior Art) The electrophotographic method has already been published by Carlson in US Patent No. 2.297.
As disclosed in No. 691, this photographic method is an ingenious combination of electrostatic and photoconductive phenomena, in which a photoconductive photoreceptor is exposed in the dark by corona discharge or the like.
表面を一様に帯電させた後、光導電性を利用して光像を
静電潜像に変え、これに着色した電荷粉体（トナー）を
付着させて可視像に変える画像形成法の一つである。An image forming method that uses photoconductivity to uniformly charge the surface and then convert the optical image into an electrostatic latent image, which is then converted into a visible image by attaching colored charged powder (toner) to it. There is one.
このような電子写真法における感光体に要求される基本
的な電気的および光電気的特性として、暗所において適
当な電位に帯電できること、この電位が適当な時間保持
できること、更に、光照射により速やかに電荷が逸散す
ることができることなどがあげられる。The basic electrical and photoelectric properties required of a photoreceptor in such electrophotography are that it can be charged to an appropriate potential in a dark place, that this potential can be maintained for an appropriate amount of time, and that it can be charged quickly by light irradiation. For example, the electric charge can be dissipated.
このような感光体において、従来より、無定形セレン、
硫化カドミウム、酸化亜鉛等の無機光導電性物質が広く
使用されてきた。これらの無機物質は上記条件は満足す
るが、いくつかの欠点も同時に有する。例えば硫化カド
ミウムや酸化亜鉛は結着剤としての樹脂に分散させて感
光体として用いられるが。In such photoreceptors, amorphous selenium,
Inorganic photoconductive materials such as cadmium sulfide and zinc oxide have been widely used. Although these inorganic materials satisfy the above conditions, they also have some drawbacks. For example, cadmium sulfide or zinc oxide is used as a photoreceptor by dispersing it in a resin as a binder.
平滑性、可撓性、硬度、引張り強度、耐摩擦性などの機
械的な欠点を有するため、そのままでは反復使用に耐え
ることができない。更に硫化カドミウムにおいては衛生
性の問題にも考慮が必要である。Since it has mechanical defects such as smoothness, flexibility, hardness, tensile strength, and abrasion resistance, it cannot withstand repeated use as it is. Furthermore, when using cadmium sulfide, consideration must also be given to hygiene issues.
また、無定形セレンにおいては、製法が蒸着によらなく
てはならず、！！造ココスト高価となるばかりでなく、
可撓性がな（、ベルト状に加工することが困難である他
、セレンの毒性および熱や機械的衝撃に対して鋭敏なた
め取り扱いには注意を要するなどの欠点を有する。In addition, for amorphous selenium, the manufacturing method must be based on vapor deposition! ! Not only is the manufacturing cost expensive, but
It has disadvantages such as being difficult to process into a belt shape, as well as being sensitive to heat and mechanical shock due to the toxicity of selenium, so it must be handled with care.
近年、これらの無機系感光体の欠点を排除するために、
有機系感光体の研究がすすみ、有機系感光体における。In recent years, in order to eliminate the drawbacks of these inorganic photoreceptors,
Research on organic photoreceptors is progressing, and organic photoreceptors.
皮膜形成の容易性、製造の容易性、軽量。Easy to form a film, easy to manufacture, lightweight.
可撓性１分光感度の多変性等の多くの利点を有するため
９種々の有機系感光体が提案され、実用に供されている
ものもある。Nine different organic photoreceptors have been proposed and some are in practical use because they have many advantages such as flexibility and polymorphism in spectral sensitivity.
例、ｔハ、 ｌ＋リーＮ−ビニルカルバゾールと２．４
゜７−ドリニトロフルオレンー９−オンとからなる感光
体（米国特許第３．４８４．２３７） 、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たもの
（特公昭４８−２５６５８号公報）、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４７−１０
７３５号公報）などである。Example, t, l + N-vinylcarbazole and 2.4
Photoreceptor consisting of ゜7-dolinitrofluoren-9-one (US Pat. No. 3,484,237), poly-N-vinylcarbazole sensitized with pyrylium salt dye (Japanese Patent Publication No. 48-25658) (Japanese Unexamined Patent Publication No. 47-10), a photoreceptor whose main component is a eutectic complex consisting of a dye and a resin
Publication No. 735).
また、更に光によりキャリアを発生する物質（キャリア
発生物質と呼ぶ）と、この発生したキャリアを輸送する
ことのできる物質（キャリア輸送物質と呼ぶ）とを組合
せた電子写真感光体が提案されている。例えば、米国特
許第３．７９１．８２６号明細書にはキャリア発生層上
にキャリア輸送層を設けた感光体が、また、米国特許第
３．７６４．３１５号明細書にはキャリア発生物質をキ
ャリア輸送物質中に分散せしめた感光層を持つ感光体が
記載されている。この種のキャリアの発生とキャリアの
輸送とを、それぞれ別の物質により機能を分担させるこ
とにより、すなわちキャリア発生物質とキャリア輸送物
質の組合せにより、その特性はより良好となり、有用な
感光体が提供される。Furthermore, electrophotographic photoreceptors have been proposed that combine a substance that generates carriers when exposed to light (called a carrier-generating substance) and a substance that can transport the generated carriers (called a carrier-transporting substance). . For example, U.S. Pat. No. 3.791.826 discloses a photoreceptor in which a carrier transport layer is provided on a carrier generation layer, and U.S. Pat. Photoreceptors have been described that have a photosensitive layer dispersed in a transport material. By assigning the functions of this type of carrier generation and carrier transport to separate substances, that is, by combining the carrier generation substance and the carrier transport substance, the characteristics can be improved and a useful photoreceptor can be provided. be done.
そして、これまで、この種の感光体において、キャリア
発生物質としてアゾ化合物を用いる多数の提案がなされ
てきた。Up to now, many proposals have been made for using an azo compound as a carrier generating substance in this type of photoreceptor.
例えば、アゾ化合物を感光層中に含有している感光体と
して特開昭５７−１０２６２９．特開昭５７−１３２１
５９．特開昭５７−１９１６４４．特開昭５７−１７６
０５５．特開昭５８−１４７７４６の各号公報等がすで
に公知である。しかしながらこれらのアゾ化合物は、感
度、残留電位あるいは繰り返し使用時の安定性などの特
性において必ずしも完全に満足し得るものではなく、ま
たキャリア輸送物質の選択範囲も限定されるなど電子写
真プロセスの幅広い要求を完全に満足させるものは未だ
見出されていないのが実情である。For example, as a photoreceptor containing an azo compound in the photosensitive layer, JP-A-57-102629. Japanese Patent Publication No. 57-1321
59. Japanese Patent Publication No. 57-191644. Japanese Patent Publication No. 57-176
055. Japanese Unexamined Patent Publication No. 58-147746 and the like are already known. However, these azo compounds do not necessarily fully satisfy the characteristics such as sensitivity, residual potential, or stability during repeated use, and the wide range of requirements for electrophotographic processes such as the limited selection range of carrier transport materials The reality is that nothing that completely satisfies these requirements has yet been found.
（発明が解決しようとする問題点）
本発明は感度、繰り返し特性、耐久性等に優れた特定の
アゾ化合物を含有する電子写真感光体を提供するもので
ある。(Problems to be Solved by the Invention) The present invention provides an electrophotographic photoreceptor containing a specific azo compound that is excellent in sensitivity, repeatability, durability, and the like.
（問題を解決するための手段）
本発明者等は鋭意研究を行った結果、特定の構造を有す
るアゾ化合物が、電子写真感光体の真に有用なキャリア
発生物質であることを発見し、更にこのキャリア発生物
質を用いた電子写真感光体が優れた性質を有することを
見出し１本発明を完成したものである。(Means for Solving the Problem) As a result of intensive research, the present inventors have discovered that an azo compound having a specific structure is a truly useful carrier-generating substance for electrophotographic photoreceptors. The present invention was completed by discovering that an electrophotographic photoreceptor using this carrier-generating substance has excellent properties.
即ち１本発明は優れた特性を有する電子写真感光体に関
して、新規な構造のアゾ化合物を用いて提供するもので
ある。Specifically, the present invention provides an electrophotographic photoreceptor having excellent properties using an azo compound having a novel structure.
本発明の目的は、新規なキャリア発生物質を含有せしめ
ることにより高感度で残留電位の少ない、さらにキャリ
ア発生の効率が高いため、複写速度の速い電子写真感光
体を提供することである。本発明の他の目的は、帯電露
光、現像、転写工程が繰り返して行われる反復転写式電
子写真用の感光体として用いた時、繰り返し使用による
疲労劣化が少なく、更に低温より高温、低湿度より高湿
度下における種々の過酷な環境下において、安定した特
性を維持する耐久性および耐環境性の優れた電子写真感
光体を提供することにある。また、これらの電子写真感
光体のうち７８０ ｎｍ以上に分光感度を有するものに
ついセはＡｒレーザー、 １ｅ−Ｎｅレーザー、半導
体レーザーを光源とするプリンター用の感光体としても
提供することができる。An object of the present invention is to provide an electrophotographic photoreceptor that has high sensitivity and low residual potential by containing a novel carrier-generating substance, and further has high carrier generation efficiency and thus has a high copying speed. Another object of the present invention is that when used as a photoreceptor for repetitive transfer type electrophotography in which charging exposure, development, and transfer steps are repeated, fatigue deterioration due to repeated use is small, and furthermore, the present invention is more effective than low temperatures, high temperatures, and low humidity. An object of the present invention is to provide an electrophotographic photoreceptor with excellent durability and environmental resistance that maintains stable characteristics under various harsh environments such as high humidity. Among these electrophotographic photoreceptors, those having spectral sensitivity at 780 nm or more can also be provided as photoreceptors for printers using Ar lasers, 1e-Ne lasers, and semiconductor lasers as light sources.
本発明のかかる目的は、キャリア発生物質として下記一
般式（１）または（ＩＩ）で示されるアゾ化合物の少な
くとも１種を含有する感光層を有することを特徴とする
電子写真感光体によって達成される。This object of the present invention is achieved by an electrophotographic photoreceptor characterized by having a photosensitive layer containing at least one azo compound represented by the following general formula (1) or (II) as a carrier generating substance. .
一般式（１） 一般式（ＩＩ） バ１ （式中、Ｒ１およびＲ框は水素原子、ハロゲン原子。General formula (1) General formula (II) Ba1 (In the formula, R1 and R frame are hydrogen atoms and halogen atoms.
アルキル基またはアルコキシ基を表し、Ａはフェノール
性水酸基を有するカップラー残基を表す。）上記一般式
（１）または（ＩＩ）におけるＡのフェノール性水酸基
を有するカフプラー残基として好ましい具体例は一般式
（Ｉ［Ｉ）ないし〔■〕で示される。It represents an alkyl group or an alkoxy group, and A represents a coupler residue having a phenolic hydroxyl group. ) Preferred specific examples of the cuff puller residue having a phenolic hydroxyl group as A in the above general formula (1) or (II) are shown by general formulas (I[I) to [■].
一般式（Ｉ［［］
一般式（ＩＶ）
一般式（Ｖ）
一般式（Ｖ［）
一般式〔■〕
（式中、Ｒ２，ＲうおよびＲ４は水素原子、置換もしく
は未置換のアルキル基、アラルキル基または了り−ル基
；２は置換もしくは未置換の芳香族炭化水素の２価基ま
たは窒素原子を環内に含む芳香族複素環の２価基を表す
。）
次に前記一般式（Ｉ）ないし〔■〕の置換基について具
体的に説明する。General formula (I[[] General formula (IV) General formula (V) General formula (V[) General formula [■]] (wherein, R2, R and R4 are hydrogen atoms, substituted or unsubstituted alkyl groups, Aralkyl group or Aryl group; 2 represents a substituted or unsubstituted divalent group of an aromatic hydrocarbon or a divalent group of an aromatic heterocycle containing a nitrogen atom in the ring.) Next, the general formula ( The substituents I) to [■] will be specifically explained.
Ｒ２，Ｒ３およびＲ４はそれぞれ水素原子；メチル基、
エチル基、プロピル基、ブチル基などの未置換アルキル
基；クロロメチル基、ヒドロキシエチル基、ジエチルア
ミノエチル基などの置換アルキル基；ベンジル基、フェ
ネチル基、シンナミル基、ナフチルメチル基などの未置
換アラルキル基；メチルベンジル基、メトキシベンジル
基、クロロベンジル基などの置換アラルキル基；フェニ
ル基、ナフチル基。R2, R3 and R4 are each hydrogen atom; methyl group,
Unsubstituted alkyl groups such as ethyl, propyl, and butyl; substituted alkyl groups such as chloromethyl, hydroxyethyl, and diethylaminoethyl; unsubstituted aralkyl groups such as benzyl, phenethyl, cinnamyl, and naphthylmethyl ; Substituted aralkyl groups such as methylbenzyl group, methoxybenzyl group, chlorobenzyl group; phenyl group, naphthyl group.
アントリル基、ピレニル基などの未置換子り−ル基；ト
リル基、メトキシフェニル基、キシリル基、メチルニト
ロフェニル基、クロロフェニル基、ジクロロフェニル基
、ニトロフェニル基、ジニトロフェニル基、クロロニト
ロフェニル基、トリフルオロメチルフェニル基、シアノ
フェニル基、クロロナフチル基ニトロナフチル基などの
置換アリール基；ピリジル基、フタラジニル基、ベンゾ
チアゾリル基、カルバゾリル基などの未置換芳香族複素
環基；メチルベンゾチアゾリル基、クロロカルバゾリル
基などの置換芳香族複素環基である。Unsubstituted ryl groups such as anthryl group and pyrenyl group; tolyl group, methoxyphenyl group, xylyl group, methylnitrophenyl group, chlorophenyl group, dichlorophenyl group, nitrophenyl group, dinitrophenyl group, chloronitrophenyl group, Substituted aryl groups such as fluoromethylphenyl group, cyanophenyl group, chloronaphthyl group, nitronaphthyl group; Unsubstituted aromatic heterocyclic groups such as pyridyl group, phthalazinyl group, benzothiazolyl group, carbazolyl group; methylbenzothiazolyl group, chloro It is a substituted aromatic heterocyclic group such as a carbazolyl group.
Ｒ／は水素原子；塩素源子、臭素原子などのハロゲン原
子；メチル基、エチル基、プロピル基などのアルキル基
；メトキシ基、エトキシ基、プロポキシ基などのアルコ
キシ基である。R/ is a hydrogen atom; a halogen atom such as a chlorine atom or a bromine atom; an alkyl group such as a methyl group, an ethyl group, or a propyl group; an alkoxy group such as a methoxy group, an ethoxy group, or a propoxy group.
またＺはフェニレン基、ナフチレン基などの未置換芳香
族炭化水素の２価基；トリレン基、キシリレン基、クロ
ルフェニレン基、ニトロフェニレン基。Further, Z is a divalent group of an unsubstituted aromatic hydrocarbon such as a phenylene group or a naphthylene group; a tolylene group, a xylylene group, a chlorphenylene group, or a nitrophenylene group.
メトキシフェニレン基、メチルナフチレン基などの置換
芳香族炭化水素の２価基；ピリジンジイル基。Divalent groups of substituted aromatic hydrocarbons such as methoxyphenylene group and methylnaphthylene group; pyridinediyl group.
トリアゾールジイル基、イミダゾールジイル基などの未
置換芳香族複素環の２価基；メチルピリジンジイル基、
クロルキノリンジイル基などの置換芳香族複素環の２価
基である。Unsubstituted aromatic heterocyclic divalent groups such as triazolediyl group and imidazolediyl group; methylpyridinediyl group,
It is a divalent group of a substituted aromatic heterocycle such as a chloroquinolinediyl group.
次に本発明のアゾ化合物の代表例を以下にあげる。Next, typical examples of the azo compound of the present invention are listed below.
前記一般式（１）で示されるアゾ化合物は、一般式〔■
〕または（ＩＸ）
一般式〔■〕
一般式（ＩＸ）
（Ｒ，は（Ｉ）またはＣＩ［］と同様）で示されるジア
ミンを常法により、ジアゾ化またはテトラゾ化し。The azo compound represented by the general formula (1) is represented by the general formula [■
] or (IX) General formula [■] A diamine represented by general formula (IX) (R, is the same as (I) or CI []) is diazotized or tetrazotized by a conventional method.
次いで各種カップラーと水またはジメチルホルムアミ−
、ジメチルスルホキシド、その他の有機溶媒中でアルカ
リの存在下でカップリングすることにより容易に得るこ
とができる。また、モノアミンまたはジアミンのジアゾ
ニウム塩またはテトラゾニウム塩をホウフッ化塩、塩化
亜鉛複塩等の形で一旦単離した後、カップリングしても
よい。このジアゾ化、カップリング反応の際、化合物中
の一部のアミノ基が未反応で残っている化合物が混在し
ていても電子写真特性に悪影響を及ぼすことはない。Next, various couplers and water or dimethylformamide
, dimethyl sulfoxide, or other organic solvent in the presence of an alkali. Alternatively, a diazonium salt or a tetrazonium salt of a monoamine or diamine may be isolated in the form of a borofluoride salt, zinc chloride double salt, etc., and then coupled. During this diazotization and coupling reaction, even if some of the amino groups in the compound remain unreacted, the electrophotographic properties will not be adversely affected.
次に本発明で用いられるアゾ化合物の代表例について、
その合成法を示°す。Next, regarding representative examples of azo compounds used in the present invention,
The synthesis method is shown below.
合成例（例示化合物（１）の合成）
下記の式〔ｘ〕で示されるアミン化合物４４．２ ｇ式
（Ｘ）
（０，１モル）を濃塩酸２β中に分散し、５℃以下に冷
却し、これに亜硝酸ナトリウム１３．８ｇ（０，２モル
）を少しづつ加える。加え終わった後、５℃以下で１時
間攪拌した後、活性炭５ｇを加え１０分間攪拌して濾過
する。得られた濾液に六フフ化リン酸アンモニウム２５
０ｇを加えて生じた結晶で濾過し。Synthesis Example (Synthesis of Exemplary Compound (1)) 44.2 g of the amine compound represented by the following formula [x] (0.1 mol) of formula (X) was dispersed in concentrated hydrochloric acid 2β and cooled to 5°C or below. Then, 13.8 g (0.2 mol) of sodium nitrite was added little by little. After the addition is complete, the mixture is stirred at 5° C. or lower for 1 hour, then 5 g of activated carbon is added, stirred for 10 minutes, and filtered. 25 ammonium hexafluoride phosphate was added to the obtained filtrate.
0g was added and filtered through the crystals formed.
テトラゾニウム塩のへキサフルオロフォスフェート塩を
得る。この結晶をＮ、Ｎ−ジメチルホルムアミド５Ｉｔ
に熔解してテトラゾニウム液を調製する。The hexafluorophosphate salt of the tetrazonium salt is obtained. This crystal was converted into N,N-dimethylformamide 5It.
Prepare a tetrazonium solution by dissolving it in
次に、２−ヒドロキシ−３−（２−クロルフェニルカル
バモイル）−ナフタレン６０ｇ（０，２モル）をＮ、Ｎ
−ジメチルホルムアミド２１に溶解した後トリエタノー
ルアミン６０ｇを加え５℃以下で攪拌しながら上記テト
ラゾニウム液を滴下する。滴下後。Next, 60 g (0.2 mol) of 2-hydroxy-3-(2-chlorophenylcarbamoyl)-naphthalene was added to N,N
- After dissolving in dimethylformamide 21, 60 g of triethanolamine is added and the above tetrazonium solution is added dropwise while stirring at 5° C. or lower. After dripping.
２０〜３０℃で２時間攪拌した後、析出した結晶を濾過
し、Ｎ、Ｎ−ジメチルホルムアミド２βでフリカケ洗浄
し、さらにアセトンおよび水で洗浄し乾燥して化合物（
１）５３ｇが得られる。After stirring at 20-30°C for 2 hours, the precipitated crystals were filtered, washed with N,N-dimethylformamide 2β, further washed with acetone and water, and dried to obtain the compound (
1) 53g is obtained.
これらの化合物は１種または２種以上を組合せて用いる
こともできる。These compounds may be used alone or in combination of two or more.
本発明の感光体は以上のようなキャリア発生物質として
特定のアゾ化合物を含有し、かつ種々のキャリア輸送物
質を含有するものであるが、これらの特定のアゾ化合物
の応用の仕方によって種々の特性の感光体が得られる。The photoreceptor of the present invention contains a specific azo compound as a carrier generating substance as described above, and also contains various carrier transport substances, but it has various characteristics depending on how these specific azo compounds are applied. A photoreceptor of 100% is obtained.
例えば、キャリア輸送物質をキャリア発生物質と同一層
中にて導電性支持基体に設けた１通常単層型感光体と称
せられる構成、もしくは、主としてキャリア発生物質を
含有する第１層と。For example, a structure usually referred to as a single-layer photoreceptor in which a carrier transport material is provided on a conductive support substrate in the same layer as a carrier-generating material, or a first layer mainly containing a carrier-generating material.
主としてキャリア輸送物質を含有する第２層を導電性支
持基体に２積層することによってなされる通常積層型感
光体と称せられる構成にて使用することができる。これ
らの構成の選択は感光体の使用する極性により、適宜選
ばれる。It can be used in a configuration commonly referred to as a laminated type photoreceptor, which is made by laminating two second layers mainly containing a carrier transporting substance on a conductive support substrate. These configurations are appropriately selected depending on the polarity of the photoreceptor used.
本発明で用いられるキャリア輸送物質は２例えばヒドラ
ゾン類、ピラゾリン類、ジアリールアルカン類、アルキ
レンジアミン類、トリフェニルアミン類。Carrier transport substances used in the present invention include hydrazones, pyrazolines, diarylalkanes, alkylene diamines, and triphenylamines.
ベンジルアニリン類、ジフェニルベンジルアミン類。Benzylanilines, diphenylbenzylamines.
トリアリールアルカン類、オキサジアゾール類、オキサ
ゾール類、スチルベン類、アントラセン類など各種の化
合物であるがこれらに限られるものではない。さらに具
体的に例をあげると次のようなものである。Various compounds include, but are not limited to, triarylalkanes, oxadiazoles, oxazoles, stilbenes, and anthracenes. A more specific example is as follows.
２Ｈ５
本発明におけるアゾ化合物およびキャリア輸送物質はそ
れ自身では皮膜形成能を有しない為、感光層として形成
せしめるには結着剤樹脂を用いる。2H5 Since the azo compound and carrier transport substance in the present invention do not have film-forming ability by themselves, a binder resin is used to form them as a photosensitive layer.
本発明において好ましく用いられる結着剤は、高い電気
絶縁性のフィルム形成性高分子重合体、あるいは共重合
体である。このような高分子重合体、共重合体であり１
本発明において好ましく用いられる結着剤はフェノール
樹脂、ポリエステル樹脂、酢酸ビニル樹脂、ポリカーボ
ネート樹脂、ポリペプチド樹脂、セルロース系樹脂、ポ
リウレタン樹脂、ポリビニルピロリドン、ポリエチレン
オキサイド、ポリ塩化ビニル樹脂、でん粉類、ポリビニ
ルアルコール。The binder preferably used in the present invention is a highly electrically insulating film-forming polymer or copolymer. These high molecular weight polymers and copolymers are 1
Binders preferably used in the present invention include phenolic resin, polyester resin, vinyl acetate resin, polycarbonate resin, polypeptide resin, cellulose resin, polyurethane resin, polyvinylpyrrolidone, polyethylene oxide, polyvinyl chloride resin, starch, and polyvinyl alcohol. .
アクリル系共重合体樹脂、塩化ビニル酢酸ビニル共重合
樹脂、メタクリル系共重合樹脂、シリコーン樹脂、ポリ
アクリロニトリル系共重合樹脂、ポリアクリルアミド、
ポリビニルブチラール、ポリビニルカルバゾール、ポリ
塩化ビニリデン樹脂、シリコーン樹脂等が挙げられる。Acrylic copolymer resin, vinyl chloride vinyl acetate copolymer resin, methacrylic copolymer resin, silicone resin, polyacrylonitrile copolymer resin, polyacrylamide,
Examples include polyvinyl butyral, polyvinyl carbazole, polyvinylidene chloride resin, and silicone resin.
これらの高分子バインダーは、単独あるいは２種以上混
合して用いられるが１本発明に使用できる結着剤は、こ
れらに限定されるものではない。更に本発明の感光体は
導電性支持体上に必要に応じて中間層を介してキャリア
発生物質を主成分とするキャリア発生層を設け、該層に
隣接してキャリア輸送物質を主成分とするキャリア輸送
層を設けた積層構成としてもよい、また、このような積
層構成にした場合。These polymer binders may be used alone or in combination of two or more, but the binders that can be used in the present invention are not limited to these. Further, in the photoreceptor of the present invention, a carrier generation layer containing a carrier generation substance as a main component is provided on the conductive support via an intermediate layer if necessary, and adjacent to the carrier generation layer the main component is a carrier transporting substance. A laminated structure including a carrier transport layer may also be used, and such a laminated structure may be used.
キャリア発生層とキャリア輸送層のどちらを上層にする
かは帯電性を正負にどちらを選ぶかによって決定される
。一般に負帯電の時はキャリア輸送層を上層にした方が
特性上有利である。また１本発明の感光体において、キ
ャリア発生層とキャリア輸送層のそれぞれの別個の層か
らなる積層構成とする場合。Which of the carrier generation layer and the carrier transport layer is to be used as the upper layer is determined depending on whether the chargeability is positive or negative. Generally, when negatively charged, it is advantageous in terms of characteristics to have a carrier transport layer as an upper layer. Further, in the photoreceptor of the present invention, there is a case where the photoreceptor has a laminated structure consisting of a carrier generation layer and a carrier transport layer, each of which is a separate layer.
感光層は導電性支持体上に直接あるいは必要に応じて接
着層あるいはバリアー層などの中間層を設けた上にキャ
リア発生物質をボールミル、アトライター等で分散溶媒
中にて微細化し、必要に応じて高分子バインダーと混合
分散して得られる分散液を塗布した後、さらにキャリア
輸送物質と高分子バインダーとをジオキサン、ジクロル
メタン、ジクロルエタン。The photosensitive layer is formed directly on the conductive support, or on top of an intermediate layer such as an adhesive layer or barrier layer provided as necessary, a carrier-generating substance is micronized in a dispersion solvent using a ball mill, an attritor, etc., as necessary. After coating the dispersion obtained by mixing and dispersing with a polymeric binder, the carrier transport substance and the polymeric binder are further mixed with dioxane, dichloromethane, or dichloroethane.
テトラヒドロフラン等の有機溶媒に溶解した溶液を塗布
することによってつくることができる。It can be produced by coating a solution dissolved in an organic solvent such as tetrahydrofuran.
また、単層型感光体の場合は、同様の有機溶媒にキャリ
ア発生物質、キャリア輸送物質および高分子バインダー
を加えて、ボールミル、アトライター等で分散した塗液
を導電性支持体に塗布することによってつくることがで
きる。In the case of a single-layer type photoreceptor, a carrier-generating substance, a carrier-transporting substance, and a polymer binder are added to the same organic solvent, and a coating liquid is dispersed using a ball mill, an attritor, etc., and then applied to the conductive support. It can be created by
また２本発明に用いるキャリア輸送物質は、結着剤１０
０重量部当りキャリア輸送物質を１０〜３００重量部が
好ましい。ただし１本発明はこの範囲のみに制限される
ものではない。また、感光層の厚さは、要求される光感
度や耐久性および、キャリア発生物質、キャリア輸送物
質の結着剤に対する混合側・ 合によって決定される
が単層型、積層型、何れにしても、支持導電性基体上の
感光層の厚さは５０ミクロン以下好ましくは７〜３０ミ
クロンぐらいが皮膜の可撓性の点からしても適当である
。In addition, the carrier transport substance used in the present invention is a binder 10
10 to 300 parts by weight of carrier transport material per 0 part by weight is preferred. However, the present invention is not limited only to this range. The thickness of the photosensitive layer is determined by the required photosensitivity and durability, as well as the mixing ratio of the carrier-generating substance and the carrier-transporting substance to the binder. Also, the thickness of the photosensitive layer on the supporting conductive substrate is preferably 50 microns or less, preferably about 7 to 30 microns, from the viewpoint of the flexibility of the film.
また、感光層には必要に応じて、保護層として役立つ層
を被覆することもできる。The photosensitive layer can also be coated with a layer that serves as a protective layer, if necessary.
本発明の電子写真感光体に用いる支持体としては導電性
が付与されていれば何れのものでも良く、従来用いられ
ているいずれのタイプの導電層であってもさしつかえな
い。具体的には、アルミニウム、銅。The support used in the electrophotographic photoreceptor of the present invention may be any support as long as it is endowed with conductivity, and any type of conductive layer conventionally used may be used. Specifically, aluminum and copper.
ステンレス、真鍮などの金属、アルミニウム、酸化イン
ジウムや酸化錫などを蒸着またはラミネートしたプラス
チックあるいは導電性粒子１例えばカーボンブラック、
！！粒子、アルミニウム粒子を分散したプラスチックな
どを挙げることができる。また、その型状については、
シート状あるいはシリンダー状その他のものであっても
差しつかえない。Metals such as stainless steel and brass, aluminum, plastics on which indium oxide, tin oxide, etc. are vapor-deposited or laminated, or conductive particles 1 For example, carbon black,
! ! Examples include plastic particles and aluminum particles dispersed therein. Also, regarding its shape,
It may be sheet-shaped, cylindrical or other.
次に本発明を実施例により、更に具体的に説明するが２
本発明は以下の実施例に限定されるものではない。以下
、実施例において例中の化合物磁は前記例中に付記した
化合物磁を示し、「部」とあるのは重量部を示す。Next, the present invention will be explained in more detail with reference to Examples.
The present invention is not limited to the following examples. Hereinafter, in the examples, the compound magnet in the example refers to the compound magnet added in the above example, and "parts" indicate parts by weight.
実施例１
化合物（１”） ０
．４部ポリエステル樹脂（バイロン２００）
０．５部１．２−ジクロロエタン
９．５部以上の組成物を振動型ミルにて２時間分散し、
得られた光導電性組成物を８０μのアルミニウム板上に
乾燥膜厚が０．５μになる様にワイヤーバーにてコート
し、１００℃に均一に加熱されたオーブン中にて１時間
乾燥させて電荷発生層を形成する。ついで以下の組成の
溶液を関整し、上記キャリア発生層上に１５μになるよ
うに。Example 1 Compound (1”) 0
．． 4-part polyester resin (Byron 200)
0.5 parts 1,2-dichloroethane
Dispersing 9.5 parts or more of the composition in a vibratory mill for 2 hours,
The resulting photoconductive composition was coated on an 80μ aluminum plate with a wire bar to a dry film thickness of 0.5μ, and dried for 1 hour in an oven uniformly heated to 100°C. Form a charge generation layer. Next, a solution having the following composition was prepared so that the layer had a thickness of 15 μm on the carrier generation layer.
化合物（ａ） ０．３
部ポリエステル樹脂（バイロン２００） ０．
４部ジクロロエタン ２．
６部からなる組成物をワイヤーバーにてコートし、８０
℃に均一に加熱されたオーブン中にて３０分間乾燥して
積層型感光体を作成した。Compound (a) 0.3
Polyester resin (Vylon 200) 0.
4 parts dichloroethane 2.
A composition consisting of 6 parts was coated with a wire bar and 80
A laminated photoreceptor was prepared by drying for 30 minutes in an oven uniformly heated to .degree.
こうして、得られたサンプルに対して−５，ＯＫＶ。-5, OKV for the sample thus obtained.
コロナギャップ１０ ｎｕ、 １０ ｍ／ｍｉｎの帯
電スピードでコロナ放電を与え、放電停止後、１０秒後
に２８５４にのタングステン光源にて５． ＯＬｕにの
照度で露光する。この時の露光直前の電位が５０％低下
するのに要した光の照射量を感度とした。この様にして
測定したサンプルは最大表面帯電量−６３０Ｖ。Corona discharge was applied with a corona gap of 10 nu and a charging speed of 10 m/min, and 10 seconds after the discharge stopped, a tungsten light source of 2854 was used. Expose to OLu at an illumination intensity. The amount of light irradiation required for the potential immediately before exposure to decrease by 50% at this time was defined as the sensitivity. The sample measured in this way had a maximum surface charge of -630V.
暗減衰率４．１％、感度’１．６ Ｌｕｘ、ｓｅｃ ＋
残留電位−１５■であった。Dark decay rate 4.1%, sensitivity '1.6 Lux, sec +
The residual potential was -15 ■.
実施例２
化合物（５） ０．４
部アクリル樹脂（ダイヤナールＨＲ１１３） ０．
２部塩化ビニル−酢酸ビニル樹脂（ＶＭＣＨ） ０
．２ｆＢ酢酸エチル １
４部以上の組成物を振動型ミルにて２時間分散し、得ら
れた光導電性組成物を厚さ５μのアルミニウム箔と７５
μのポリエステルフィルムとのラミネートフィルム上に
乾燥膜厚が０．５μになる様にワイヤーバーにてコート
し、１３０℃に均一に加熱されたオーブン中にて１時間
置きキャリア発生層を形成する。Example 2 Compound (5) 0.4
Part acrylic resin (Dianal HR113) 0.
2 parts vinyl chloride-vinyl acetate resin (VMCH) 0
．． 2fB ethyl acetate 1
4 parts or more of the composition was dispersed in a vibrating mill for 2 hours, and the resulting photoconductive composition was coated with a 5 μm thick aluminum foil and 75 μm thick.
A carrier-generating layer is formed by coating the laminate film with a polyester film of 0.5 μm using a wire bar so that the dry film thickness becomes 0.5 μm, and leaving it in an oven uniformly heated to 130° C. for 1 hour.
ついで実施例１において、化合物（ａ）の代りに（ｂ）
を用いて、実施例１と同様に積層型感光体を作成して試
験したところ、最大表面帯電量−６１０Ｖ。Then, in Example 1, compound (b) was substituted for compound (a).
When a laminated photoreceptor was prepared and tested in the same manner as in Example 1, the maximum surface charge amount was -610V.
暗減衰率５．８％、感度２．９ Ｌｕｘ−ｓｅｃ ＋
残留電位−１３Ｖであった。Dark decay rate 5.8%, sensitivity 2.9 Lux-sec +
The residual potential was -13V.
実施例３
化合物（８） １部化
合物（ｄ） ２．５部
アクリルポリオール（タケラックＡ〜７０２）３．６部
エポキシ樹脂（エポン１００７） ０．５
部メチルエチルケトン １．２
部セロソルブアセテート１．２部
以上の組成物を磁性ボールミルにて４８時間練肉を行い
光導電性組成物を得る。Example 3 Compound (8) 1 part Compound (d) 2.5 parts Acrylic polyol (Takelac A-702) 3.6 parts Epoxy resin (Epon 1007) 0.5 parts
Part methyl ethyl ketone 1.2
A composition containing 1.2 parts or more of cellosolve acetate is milled in a magnetic ball mill for 48 hours to obtain a photoconductive composition.
次にこの組成物を８０μのアルミ板上に乾燥膜厚が８μ
になるようにワイヤーバーにてコートシ、１１０°Ｃに
均一に加熱されたオーブン中に１時間置き単層型感光体
とした。こうして、得られたサンプルに対して、実施例
１に従い、コロナ放電＋５．７ Ｋ Ｖとして測定した
ところ、最大表面帯電量５６０Ｖ。Next, this composition was placed on an 80μ aluminum plate to a dry film thickness of 8μ.
The sample was coated with a wire bar so that the photoreceptor was coated with a wire bar, and placed in an oven uniformly heated to 110° C. for 1 hour to obtain a single-layer photoreceptor. According to Example 1, the obtained sample was measured as a corona discharge of +5.7 KV, and the maximum surface charge amount was 560V.
暗減衰率９．１％、感度２．４ Ｌｕｘ−ｓｅｃ 、
残留電位−１２Ｖであった。Dark decay rate 9.1%, sensitivity 2.4 Lux-sec,
The residual potential was -12V.
実施例４
実施例１において、化合物（１）の代りに（３）を用い
、ポリエステル樹脂（バイロン２００）の代りに、ポリ
カーボネート樹脂（パンライトＬ−１２５０）を用いて
、実施例１と同様に、積層型感光体を作成した。こうし
て得られたサンプルを実施例１と同様に測定したところ
、最大表面帯電！−６８０■、暗減衰率１０．８％、感
度２．８ Ｌｕｘ−ｓｅｃ 、残留電位−１９Ｖであ
った。Example 4 The same procedure as in Example 1 was carried out, except that compound (3) was used instead of compound (1) and polycarbonate resin (Panlite L-1250) was used instead of polyester resin (Vylon 200). , a laminated photoreceptor was created. When the sample thus obtained was measured in the same manner as in Example 1, the maximum surface charge was found! -680■, dark decay rate 10.8%, sensitivity 2.8 Lux-sec, and residual potential -19V.
実施例５〜１６
実施例４のキャリア発生材料、キャリア輸送材料を以下
の表に示す材料に代えて、同様に試験した。Examples 5 to 16 The carrier-generating material and carrier-transporting material of Example 4 were replaced with the materials shown in the table below, and tests were conducted in the same manner.
本発明は以上のような構成よりなり、その使用に際し、
正帯電、および負帯電においても高感度にして、また、
繰り返しによる感光体の劣化も少な（。The present invention has the above configuration, and when using it,
High sensitivity even in positive and negative charging, and
There is little deterioration of the photoreceptor due to repeated use.
また実用上において、低温から高温度まで、また低湿度
から高湿度下までにおける帯電保持力、感度変化におけ
る環境性、耐久性の優れた特徴を有する。In addition, in practical use, it has excellent characteristics such as charge retention ability from low to high temperatures and from low humidity to high humidity, environmental friendliness with respect to sensitivity changes, and durability.
表table
Claims (1)
で示されるアゾ化合物の少なくとも１種を含有する感光
層を有することを特徴とする電子写真感光体。 一般式〔 I 〕 ▲数式、化学式、表等があります▼ 一般式〔II〕 ▲数式、化学式、表等があります▼ （式中、Ｒ＿１は水素原子、ハロゲン原子、アルキル基
またはアルコキシ基を表し、Ａはフェノール性水酸基を
有するカップラー残基を表す。） ２、上記一般式〔 I 〕または〔II〕のＡが下記の一般
式〔III〕〜〔VII〕で表わされる特許請求の範囲第１項
記載の電子写真感光体。 一般式〔III〕 ▲数式、化学式、表等があります▼ 一般式〔IV〕 ▲数式、化学式、表等があります▼ 一般式〔Ｖ〕 ▲数式、化学式、表等があります▼ 一般式〔VI〕 ▲数式、化学式、表等があります▼ 一般式〔VII〕 ▲数式、化学式、表等があります▼ （式中、Ｒ＿２、Ｒ＿３およびＲ＿４は水素原子、置換
もしくは未置換のアルキル基、アラルキル基またはアリ
ール基；Ｚは置換もしくは未置換の芳香族炭化水素の２
価基または窒素原子を環内に含む芳香族複素環の２価基
を表す。） ３、前記感光層がキャリア輸送物質とキャリア発生物質
とを含有し、当該キャリア発生物質が前記一般式〔 I
〕または〔II〕で表されるアゾ化合物である特許請求の
範囲第１項記載の電子写真感光体。 ４、前記感光層が前記一般式〔 I 〕または〔II〕で表
されるアゾ化合物であるキャリア発生物質を含有するキ
ャリア発生層とキャリア輸送物質を含有するキャリア輸
送層との積層体で構成されている特許請求の範囲第１項
記載の電子写真感光体。[Claims] 1. The following general formula [I] or [II] is formed on a conductive support.
An electrophotographic photoreceptor comprising a photosensitive layer containing at least one azo compound represented by the following. General formula [I] ▲There are mathematical formulas, chemical formulas, tables, etc.▼ General formula [II] ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, R_1 represents a hydrogen atom, a halogen atom, an alkyl group, or an alkoxy group, A represents a coupler residue having a phenolic hydroxyl group.) 2. Claim 1, in which A in the above general formula [I] or [II] is represented by the following general formulas [III] to [VII]. The electrophotographic photoreceptor described above. General formula [III] ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ General formula [IV] ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ General formula [V] ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ General formula [VI] ▲There are mathematical formulas, chemical formulas, tables, etc.▼ General formula [VII] ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, R_2, R_3, and R_4 are hydrogen atoms, substituted or unsubstituted alkyl groups, aralkyl groups, or aryl Group; Z is substituted or unsubstituted aromatic hydrocarbon 2
Represents a valent group or a divalent group of an aromatic heterocycle containing a nitrogen atom in the ring. ) 3. The photosensitive layer contains a carrier transporting substance and a carrier generating substance, and the carrier generating substance has the above general formula [I
The electrophotographic photoreceptor according to claim 1, which is an azo compound represented by ] or [II]. 4. The photosensitive layer is composed of a laminate of a carrier generation layer containing a carrier generation substance which is an azo compound represented by the general formula [I] or [II] and a carrier transport layer containing a carrier transport substance. An electrophotographic photoreceptor according to claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP26202986A JPS63116157A (en) | 1986-11-05 | 1986-11-05 | Electrophotographic sensitive body |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP26202986A JPS63116157A (en) | 1986-11-05 | 1986-11-05 | Electrophotographic sensitive body |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63116157A true JPS63116157A (en) | 1988-05-20 |
| JPH0560862B2 JPH0560862B2 (en) | 1993-09-03 |
Family
ID=17370035
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP26202986A Granted JPS63116157A (en) | 1986-11-05 | 1986-11-05 | Electrophotographic sensitive body |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63116157A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005075738A (en) * | 2003-08-28 | 2005-03-24 | Mitsui Chemicals Inc | Naphthalenecarboxylic acid derivative and electrophotographic photoreceptor and electrophotographic apparatus using the same compound |
-
1986
- 1986-11-05 JP JP26202986A patent/JPS63116157A/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005075738A (en) * | 2003-08-28 | 2005-03-24 | Mitsui Chemicals Inc | Naphthalenecarboxylic acid derivative and electrophotographic photoreceptor and electrophotographic apparatus using the same compound |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0560862B2 (en) | 1993-09-03 |
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