JPH0560861B2 - - Google Patents
Info
- Publication number
- JPH0560861B2 JPH0560861B2 JP25182886A JP25182886A JPH0560861B2 JP H0560861 B2 JPH0560861 B2 JP H0560861B2 JP 25182886 A JP25182886 A JP 25182886A JP 25182886 A JP25182886 A JP 25182886A JP H0560861 B2 JPH0560861 B2 JP H0560861B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- general formula
- carrier
- electrophotographic photoreceptor
- 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.)
- Expired - Lifetime
Links
- 108091008695 photoreceptors Proteins 0.000 claims description 47
- -1 azo compound Chemical group 0.000 claims description 32
- 239000000126 substance Substances 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 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
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
- 229910052717 sulfur Chemical group 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 239000010410 layer Substances 0.000 description 34
- 150000001875 compounds Chemical class 0.000 description 17
- 239000000463 material Substances 0.000 description 13
- 239000000203 mixture Substances 0.000 description 11
- 230000035945 sensitivity Effects 0.000 description 11
- 239000011230 binding agent Substances 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 229920005989 resin Polymers 0.000 description 9
- 239000011347 resin 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 5
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 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
- 238000003756 stirring Methods 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
- 229910052980 cadmium sulfide Inorganic materials 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 3
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 3
- 229910052711 selenium Inorganic materials 0.000 description 3
- 239000011669 selenium Substances 0.000 description 3
- 239000002356 single layer Substances 0.000 description 3
- 239000000758 substrate 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
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 229920006026 co-polymeric resin Polymers 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000001035 drying Methods 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
- 125000004957 naphthylene group Chemical group 0.000 description 2
- 230000036211 photosensitivity Effects 0.000 description 2
- 229920005668 polycarbonate resin Polymers 0.000 description 2
- 239000004431 polycarbonate resin Substances 0.000 description 2
- 229920000642 polymer Polymers 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
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000012546 transfer Methods 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
- 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
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 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
- 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
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 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
- 125000001309 chloro group Chemical group Cl* 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
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 125000004802 cyanophenyl group Chemical group 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
- 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
- 150000007857 hydrazones Chemical class 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
- 238000004898 kneading Methods 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
- 238000004519 manufacturing process Methods 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
- 125000001624 naphthyl 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
- 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
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 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
- 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
- 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
- 230000003595 spectral effect Effects 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 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
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 230000002194 synthesizing effect Effects 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
- 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
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 125000005023 xylyl 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
-
- 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
- G03G5/0677—Monoazo dyes
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Photoreceptors In Electrophotography (AREA)
Description
〔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ヤリア発生物
質として特定のアゾ化合物を含有せしめることに
より、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。
(従来の技術)
電子写真法は既にカールソンが米国特許第
2297691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、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。
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。
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、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。
更に硫化カドミカムにおいては衛生性の問題にも
考慮が必要である。
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、製造コストが高価となるば
かりでなく、可撓性がなく、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。
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、皮膜形成の容易性、製造の容易
性、軽量、可撓性、分光感度の多変性等の多くの
利点を有するため、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。
例えば、ポリ−N−ビニルカルバゾールと2,
4,7−トリニトロフルオレン−9−オンとから
なる感光体(米国特許第3484237)、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
47−10735号公報)などである。
また、更に光によりキヤリアを発生する物質
(キヤリア発生物質と呼ぶ)と、この発生したキ
ヤリアを輸送することのできる物質(キヤリア輸
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3791826号明
細書にはキヤリア発生層上にキヤリア輸送層を設
けた感光体が、また、米国特許第3764315号明細
書にはキヤリア発生物質をキヤリア輸送物質中に
分散せしめた感光層を持つ感光体が記載されてい
る。この種のキヤリアの発生とキヤリアの輸送と
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、すなわちキヤリア発生物質とキヤリア
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。
そして、これまで、この種の感光体において、
キヤ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。
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−
132159、特開昭57−191644、特開昭57−176055、
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、またキヤ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。
(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。
〔発明の構成〕
(問題を解決するための手段)
本発明者等は鋭意研究を行つた結果、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
有用なキヤリア発生物質であることを発見し、更
にこのキヤ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、本発明を完
成したものである。
即ち、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。
本発明の目的は、新規なキヤリア発生物質を含
有せしめることにより高感度で残留電位の少な
い、さらにキヤ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780nm以上に
分光感度を有するものについてはArレーザー、
He−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。
本発明のかかる目的は、キヤリア発生物質とし
て下記一般式〔〕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つて達成される。
一般式〔〕
(式中、R1およびR2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
フエノール性水酸基を有するカツプラー残基を表
す。Xは酸素原子または硫黄原子、Yは直接結
合、ビニレン基もしくは置換基を有していてもよ
いフエニレン基を表す。また、m,nは0または
1を表すが、m,nのうち少なくとも一方は0で
はないものとする。)
上記一般式〔〕におけるAのフエノール性水
酸基を有するカツプラー残基として好ましい具体
例は一般式〔〕ないし〔〕で示される。
一般式〔〕
一般式〔〕
一般式〔〕
一般式〔〕
一般式〔〕
(式中R3,R4およびR5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。)
次に前記一般式〔〕ないし〔〕の置換基に
ついて具体的に説明する。
R3,R4およびR5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、フエネチル基、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;フエニ
ル基、ナフチル基、アントリル基、ピレニル基な
どの未置換アリール基;トリル基、メトキシフエ
ニル基、キシリル基、メチルニトロフエニル基、
クロロフエニル基、ジクロロフエニル基、ニトロ
フエニル基、ジニトロフエニル基、クロロニトロ
フエニル基、トリフルオロメチルフエニル基、シ
アノフエニル基、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。
R1およびR2は水素原子;塩素原子、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。
またZはフエニレン基、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、クロルフエニレン基、ニトロフエニレ
ン基、メトキシフエニレン基、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、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。
次に本発明のアゾ化合物の代表例を以下にあげ
る。
前記一般式〔〕で示されるアゾ化合物は、一
般式〔〕
一般式〔〕
(R1,R2,X,Y,mおよびnは〔〕と同
様)で示されるモノアミンまたはジアミンを常法
により、ジアゾ化またはテトラゾ化し、次いで各
種カツプラーと水またはジメチルホルムアミド、
ジメチルスルホキシド、その他の有機溶媒中でア
ルカリの存在下でアツ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
塩をホウフツ化塩、塩化亜鉛複塩等の形で一旦単
離した後、カツプリングしてもよい。このジアゾ
化、カツプリング反応の際、化合物中の一部のア
ミノ基が未反応で残つ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。
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。
合成例
(例示化合物(1)の合成)
ビス〔2−(6−アミノベンゾチアゾリル)〕
29.8g(0.1モル)を濃塩酸2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。加え終わつた後、
5℃以下で1時間撹拌した後、活性炭5gを加え
10分間撹拌して濾過する。得られた濾液に六フツ
化リン酸アンモニウム250gを加えて生じた結晶
で濾過し、テトラゾニウム塩のヘキサフルオロフ
オスフエート塩を得る。この結晶をN,N−ジメ
チルホルムアミド5に溶解してテトラゾニウム
液を調製する。
次に、2−ヒドロキシ−3−(2−クロルフエ
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2に溶解した
後トリエタノールアミン60gを加え5℃以下で撹
拌しながら上記テトラゾニウム液を滴下する。滴
下後、20〜30℃で2時間撹拌した後、析出した結
晶を濾過し、N,N−ジメチルホルムアミド2
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。
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。
本発明の感光体は以上のようなキヤリア発生物
質として特定のアゾ化合物を含有し、かつ種々の
キヤ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つて種々
の特性の感光体が得られる。例えば、キヤリア輸
送物質をキヤリア発生物質と同一層中にて導電性
支持基体に設けた、通常単層型感光体と称せられ
る構成、もしくは、主としてキヤリア発生物質を
含有する第1層と、主としてキヤリア輸送物質を
含有する第2層を導電性支持基体に2積層するこ
とによつ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。
本発明で用いられるキヤリア輸送物質は、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、トリフエニルア
ミン類、ベンジルアニリン類、ジフエニルベンジ
ルアミン類、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。
本発明におけるアゾ化合物およびキヤリア輸送
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。
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イ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、本発明において好ましく用
いられる結着剤はフエノール樹脂、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、
ポリベプチド樹脂、セルロース樹脂、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、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。
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、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ヤリア発生物質を主成分と
するキヤリア発生層を設け、該層に隣接してキヤ
リア輸送物質を主成分とするキヤリア輸送層を設
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、キヤリア発生層とキヤリア輸
送層のどちらを上層にするかは帯電性を正負にど
ちらを選ぶかによつて決定される。一般に負帯電
の時はキヤリア輸送層を上層にした方が特性上有
利である。また、本発明の感光体において、キヤ
リア発生層とキヤ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、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ヤリ
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、さらにキヤ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、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つてつくることができ
る。
また、単層型感光体の場合は、同様の有機溶媒
にキヤリア発生物質、キヤ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
ことによつてつくることができる。
また、本発明に用いるキヤリア輸送物質は、結
着剤100重量部当りキヤリア輸送物質を10〜300重
量部が好ましい。ただし、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、キヤリア
発生物質、キヤリア輸送物質の結着剤に対する混
合割合によつ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。
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。
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
であつてもさしつかえない。具体的には、アルミ
ニウム、銅、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ツクあるいは導電性
粒子、例えばカーボンブラツク、錫粒子、アルミ
ニウム粒子を分散したプラスチツクなどを挙げる
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つて
も差しつかえない。
次に本発明を実施例により、更に具体的に説明
するが、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No.
は前記例中に付記した化合物No.を示し、「部」と
あるのは重量部を示す。
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調整し、上記キヤリア発
生層上に15μになるように、
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。
こうして、得られたサンプルに対して−
5.0KV、コロナギヤツプ10mm、10m/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2854Kのタングステン光源にて5.0Lux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−
680V、暗減衰率3.6%、感度2.7Lux.sec、残留電
位−12Vであつた。
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) 0.2部
酢酸エチル 14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75μのポリエステルフイルムとのラミネー
トフイ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時間置きキヤリア発生層を形成
する。ついで実施例1において、化合物(a)の代わ
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−
590V、暗減衰率6.9%、感度3.0Lux・sec、残留
電位−15Vであつた。
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(タケラツク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。
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し、
110℃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+
5.7KVとして測定したところ、最大表面帯電量
540V、暗減衰率8.9%、感度2.9Lux・sec、残留
電位−19Vであつた。
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、最大表面帯電量−700V、
暗減衰率10.3%、感度2.4Lux・sec、残留電位−
21Vであつた。
実施例 5〜16
実施例4のキヤリア発生材料、キヤリア輸送材
料を以下の表に示す材料に代えて、同様に試験し
た。
[Object of the invention] (Industrial application field) The present invention relates to an electrophotographic photoreceptor,
More specifically, the present invention provides a novel electrophotographic photoreceptor having excellent photosensitivity and durability by incorporating a specific azo compound as a carrier generating substance on a conductive support. (Prior art) Electrophotography has already been published by Carlson in the US Patent No.
As disclosed in No. 2297691, this photographic method is a clever combination of electrostatic and photoconductive phenomena, in which the surface of a photoconductive photoreceptor is uniformly charged by corona discharge etc. in a dark place. This is an image forming method in which the optical image is converted into an electrostatic latent image using photoconductivity, and colored charged powder (toner) is attached to the image to convert it into a visible image. The basic electrical and photoelectric properties required of the photoreceptor in such electrophotography are as follows:
The characteristics include being able to be charged to an appropriate potential in a dark place, being able to maintain this potential for an appropriate amount of time, and being able to quickly dissipate the charge by light irradiation. In such photoreceptors, inorganic photoconductive substances such as amorphous selenium, 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 and zinc oxide are used as photoreceptors by being dispersed in resin as a binder, but they have mechanical drawbacks such as smoothness, flexibility, hardness, tensile strength, and abrasion resistance.
As it is, it cannot withstand repeated use.
Furthermore, with regard to cadmium sulfide, hygiene issues must also be considered. In addition, amorphous selenium must be manufactured by vapor deposition, which not only increases the manufacturing cost but also makes it difficult to process into a belt shape due to lack of flexibility, as well as the toxicity of selenium. It also has disadvantages such as being sensitive to heat and mechanical shock and requiring careful handling. In recent years, in order to eliminate the drawbacks of these inorganic photoreceptors, research into organic photoreceptors has progressed. Various organic photoreceptors have been proposed, and some are in practical use because they have many advantages such as polymorphism. For example, poly-N-vinylcarbazole and 2,
Photoreceptor consisting of 4,7-trinitrofluoren-9-one (US Patent No. 3484237), poly-N-vinylcarbazole sensitized with pyrylium salt dye (Japanese Patent Publication No. 25658/1989), dye A photoreceptor whose main component is a eutectic complex consisting of
47-10735). Furthermore, electrophotographic photoreceptors have been proposed that combine a substance that generates carriers with 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 generating layer, and U.S. Pat. No. 3,764,315 discloses a photoreceptor in which a carrier-generating material is dispersed in a carrier-transport material. Photoreceptors with layers are described. By assigning the functions of this type of carrier generation and carrier transport to different 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. Until now, in this type of photoreceptor,
A number of proposals have been made to use azo compounds as carrier generators. For example, as a photoreceptor containing an azo compound in the photosensitive layer, JP-A-57-102629 and JP-A-57-
132159, JP-A-57-191644, JP-A-57-176055,
JP-A-58-147746 and other publications are already known. However, these azo compounds have limited sensitivity,
However, it is not always possible to completely satisfy the characteristics such as residual potential or stability during repeated use, and the selection range of carrier transport materials is also limited, so that no one has yet been found that fully satisfies the wide range of requirements of the electrophotographic process. The reality is that it has not been published. (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. [Structure of the Invention] (Means for Solving the Problem) As a result of intensive research, the present inventors have found that an azo compound having a specific structure is a truly useful carrier generating substance for electrophotographic photoreceptors. They discovered that an electrophotographic photoreceptor using this carrier-generating substance has excellent properties, and completed the present invention. That is, the present invention provides an electrophotographic photoreceptor having excellent properties using an azo compound having a novel structure. 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 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, it is more effective than low temperatures, high temperatures, and low humidity. Under various harsh environments with high humidity,
An object of the present invention is to provide an electrophotographic photoreceptor that maintains stable characteristics and has excellent durability and environmental resistance. In addition, among these electrophotographic photoreceptors, those with spectral sensitivity of 780 nm or more are used with Ar laser,
It can also be provided as a photoreceptor for printers using He-Ne lasers or semiconductor lasers as light sources. 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 [] as a carrier generating substance. General formula [] (In the formula, R 1 and R 2 represent a hydrogen atom, a halogen atom, an alkyl group or an alkoxy group, A represents a coupler residue having a phenolic hydroxyl group, X is an oxygen atom or a sulfur atom, Y is a direct bond, Represents a vinylene group or a phenylene group which may have a substituent. Also, m and n represent 0 or 1, but at least one of m and n shall not be 0.) The above general formula [ Preferred specific examples of the coupler residue having a phenolic hydroxyl group in A are shown in the general formulas [] to []. General formula [] General formula [] General formula [] General formula [] General formula [] (In the formula, R 3 , R 4 and R 5 are a hydrogen atom, a substituted or unsubstituted alkyl group, an aralkyl group or an aryl group; Z is a substituted or unsubstituted divalent group of an aromatic hydrocarbon or a nitrogen atom in the ring) represents a divalent group of an aromatic heterocycle contained in the following.) Next, the substituents in the above general formulas [] to [] will be specifically explained. R 3 , R 4 and R 5 are each a hydrogen atom; unsubstituted alkyl groups such as methyl, ethyl, propyl and butyl; substituted alkyl groups such as chloromethyl, hydroxyethyl and diethylaminoethyl; benzyl , phenethyl group, cinnamyl group, naphthylmethyl group; substituted aralkyl group such as methylbenzyl group, methoxybenzyl group, chlorobenzyl group; unsubstituted aryl group such as phenyl group, naphthyl group, anthryl group, pyrenyl group Group; tolyl group, methoxyphenyl group, xylyl group, methylnitrophenyl group,
Substituted aryl groups such as chlorophenyl group, dichlorophenyl group, nitrophenyl group, dinitrophenyl group, chloronitrophenyl group, trifluoromethylphenyl group, cyanophenyl group, chloronaphthyl group, nitronaphthyl group; pyridyl group, phthalazinyl group, benzothiazolyl group and unsubstituted aromatic heterocyclic groups such as carbazolyl groups; substituted aromatic heterocyclic groups such as methylbenzothiazolyl groups and chlorocarbazolyl groups. R 1 and R 2 are 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. Z is a divalent group of an unsubstituted aromatic hydrocarbon such as a phenylene group or a naphthylene group; or a divalent group of an unsubstituted aromatic hydrocarbon such as a phenylene group or a naphthylene group; Divalent group; divalent group of unsubstituted aromatic heterocycle such as pyridinediyl group, triazolediyl group, imidazolediyl group; divalent group of substituted aromatic heterocycle such as methylpyridinediyl group, chloroquinolinediyl group . Next, typical examples of the azo compound of the present invention are listed below. The azo compound represented by the general formula [] is represented by the general formula [] General formula [] A monoamine or diamine represented by (R 1 , R 2 ,
It can be easily obtained by coupling in 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 a compound in which some of the amino groups in the compound remain unreacted is present, the electrophotographic properties will not be adversely affected. Next, a method for synthesizing representative examples of the azo compound used in the present invention will be shown. Synthesis example (Synthesis of exemplified compound (1)) Bis[2-(6-aminobenzothiazolyl)]
Disperse 29.8g (0.1 mol) in concentrated hydrochloric acid 2,
Cool to below ℃ and add 13.8g of sodium nitrite to this.
(0.2 mol) little by little. After adding
After stirring for 1 hour at 5℃ or below, 5g of activated carbon was added.
Stir for 10 minutes and filter. 250 g of ammonium hexafluorophosphate is added to the obtained filtrate and filtered through the resulting crystals to obtain a hexafluorophosphate salt of a tetrazonium salt. This crystal is dissolved in N,N-dimethylformamide 5 to prepare a tetrazonium solution. Next, 60 g (0.2 mol) of 2-hydroxy-3-(2-chlorophenylcarbamoyl)-naphthalene
After dissolving 2 in N,N-dimethylformamide, 60 g of triethanolamine was added, and the above tetrazonium solution was added dropwise while stirring at 5° C. or lower. After the dropwise addition, the precipitated crystals were filtered after stirring at 20 to 30°C for 2 hours, and N,N-dimethylformamide 2
After washing with acetone and water and drying, 53 g of compound (1) is obtained. These compounds may be used alone or in combination of two or more. 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. A photoreceptor with the following characteristics can be obtained. For example, a structure in which a carrier transport material is provided on a conductive support substrate in the same layer as a carrier generating material, which is usually referred to as a single-layer photoreceptor, or a structure in which a first layer containing mainly a carrier generating material and a first layer containing mainly a carrier It can be used in a configuration commonly referred to as a laminated photoreceptor, which is formed by laminating two second layers containing a transport substance on a conductive support substrate. The selection of these structures is appropriately selected depending on the polarity of the photoreceptor used. Carrier transport substances used in the present invention include, for example, hydrazones, pyrazolines, diarylalkanes, alkylene diamines, triphenylamines, benzylanilines, diphenylbenzylamines, triarylalkanes, oxadiazoles, Various compounds include, but are not limited to, oxazoles, stilbenes, and anthracenes. A more specific example is as follows. 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 the photosensitive layer. The binder preferably used in the present invention is
Highly electrically insulating film-forming polymer,
Or it is a copolymer. Among such polymers and copolymers, binders preferably used in the present invention include phenol resins, polyester resins, vinyl acetate resins, polycarbonate resins,
Polypeptide resin, cellulose resin, polyurethane resin, polyvinylpyrrolidone, polyethylene oxide, polyvinyl chloride resin, starch, polyvinyl alcohol, acrylic copolymer resin, vinyl chloride vinyl acetate copolymer resin, methacrylic copolymer resin, silicone resin, Examples include polyacrylonitrile copolymer resin, polyacrylamide, polyvinyl butyral, polyvinyl carbazole, polyvinylidene chloride resin, silicone resin, and the like. These polymeric binders may be used alone or in combination.
Although more than one type of binder can be used as a mixture, the binder that can be used in the present invention is not limited to these.
Further, in the photoreceptor of the present invention, a carrier generation layer containing a carrier-generating substance as a main component is provided on the conductive support via an intermediate layer if necessary, and adjacent to the carrier-generating layer, the carrier-generating layer mainly contains a carrier transport substance. A laminated structure including a carrier transport layer may also be used. In addition, in the case of such a laminated structure, which of the carrier generation layer and the carrier transport layer is to be the upper layer is determined by choosing 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. In addition, when the photoreceptor of the present invention has a laminated structure consisting of separate layers of a carrier generation layer and a carrier transport layer, the photosensitive layer is placed directly on the conductive support or, if necessary, with an adhesive layer or barrier layer. After forming an intermediate layer such as a carrier-generating material, micronize the carrier-generating substance in a dispersion solvent using a ball mill, attritor, etc., and applying a dispersion obtained by mixing and dispersing it with a polymer binder as necessary, further carrier-generating material is applied. It can be prepared by applying a solution of the transport material and the polymeric binder dissolved in an organic solvent such as dioxane, dichloromethane, dichloroethane, tetrahydrofuran, or the like. In the case of a single-layer 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 made by Further, the carrier transport material used in the present invention preferably contains 10 to 300 parts by weight per 100 parts by weight of the binder. 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 and 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
A thickness of 50 microns or less, preferably about 7 to 30 microns, is suitable from the viewpoint of film flexibility. The photosensitive layer can also be coated with a layer that serves as a protective layer, if necessary. 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, metals such as aluminum, copper, stainless steel, and brass, plastics on which aluminum, indium oxide, tin oxide, etc. are vapor-deposited or laminated, and conductive particles such as carbon black, tin particles, and aluminum particles dispersed therein are used. can be mentioned. Moreover, the shape may be sheet-like, cylindrical, or other. Next, the present invention will be explained in more detail with reference to Examples, but the present invention is not limited to the following Examples. In the examples below, compound No.
indicates the compound number added in the above example, and "parts" indicates parts by weight. Example 1 Compound (1) 0.4 parts Polyester resin (Vylon 200) 0.5 parts 1,2-dichloroethane 9.5 parts The above composition was dispersed 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, dried for 1 hour in an oven uniformly heated to 100°C, and charged. Forms a generation layer. Next, a solution having the following composition was prepared, and a composition consisting of 0.3 parts of compound (a), 0.4 parts of polyester resin (Vylon 200), and 2.6 parts of dichloroethane was coated on the carrier generating layer to a thickness of 15 μm using a wire bar. , 80
A laminated photoreceptor was prepared by drying for 30 minutes in an oven uniformly heated to .degree. Thus, for the sample obtained -
A corona discharge is applied at 5.0KV, a corona gap of 10mm, and a charging speed of 10m/min, and after 10 seconds after the discharge stops, it is exposed to a 2854K tungsten light source at an illuminance of 5.0Lux. 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 has a maximum surface charge of -
680V, dark decay rate 3.6%, sensitivity 2.7Lux.sec, residual potential -12V. Example 2 Compound (5) 0.4 parts Acrylic resin (Dianal HR113) 0.2 parts Vinyl chloride-vinyl acetate resin (VMCH) 0.2 parts Ethyl acetate 14 parts The above composition was dispersed in a vibratory mill for 2 hours,
The resulting photoconductive composition was coated on a laminate film of 5μ thick aluminum foil and 75μ polyester film with a wire bar to a dry film thickness of 0.5μ, and heated uniformly to 130°C. The mixture was left in a heated oven for 1 hour to form a carrier generation layer. Next, in Example 1, a laminated photoreceptor was prepared and tested in the same manner as in Example 1 using compound (b) in place of compound (a), and the maximum surface charge amount -
The voltage was 590V, dark decay rate 6.9%, sensitivity 3.0Lux·sec, and residual potential -15V. Example 3 Compound (8) 1 part Compound (d) 2.5 parts Acrylic polyol (Takerak A-702) 3.6 parts Epoxy resin (Epon 1007) 0.5 parts Methyl ethyl ketone 1.2 parts Cellosolve acetate 1.2 parts The above composition was milled in a magnetic ball mill for 48 hours. A photoconductive composition is obtained by kneading for a time. Next, this composition was coated on an 80μ aluminum plate using a wire bar so that the dry film thickness was 8μ.
It was placed in an oven uniformly heated to 110° C. for 1 hour to form a single-layer photoreceptor. According to Example 1, corona discharge +
Maximum surface charge when measured at 5.7KV
The voltage was 540V, dark decay rate 8.9%, sensitivity 2.9Lux·sec, and residual potential -19V. Example 4 In Example 1, compound (3) was used instead of compound (1), and instead of polyester resin (Vylon 200),
A laminated photoreceptor was prepared in the same manner as in Example 1 using polycarbonate resin (Panlite L-1250). When the sample thus obtained was measured in the same manner as in Example 1, the maximum surface charge amount was -700V,
Dark decay rate 10.3%, sensitivity 2.4Lux・sec, residual potential -
It was 21V. Examples 5 to 16 The same tests were conducted except that the carrier generation material and carrier transport material of Example 4 were replaced with the materials shown in the table below.
【表】【table】
本発明は以上のような構成よりなり、その使用
に際に、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
なく、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。
The present invention has the above-mentioned structure, and when used, it has high sensitivity in both positive and negative charging, and there is little deterioration of the photoreceptor due to repeated use. It has excellent characteristics such as charge retention ability from low humidity to high humidity, environmental friendliness with respect to sensitivity changes, and durability.
Claims (1)
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〔〕 (式中、R1およびR2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
フエノール性水酸基を有するカツプラー残基を表
す。Xは酸素原子または硫黄原子、Yは直接結合
もしくはビニレン基を表す。また、m,nは0ま
たは1を表すが、m,nのうち少なくとも一方は
0ではないものとする。) 2 上記一般式〔〕のXがイオウ原子である特
許請求の範囲第1項記載の電子写真感光体。 3 上記一般式〔〕のAが下記の一般式〔〕
〜〔〕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〔〕 一般式〔〕 一般式〔〕 一般式〔〕 一般式〔〕 (式中R3,R4およびR5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。) 4 前記感光層がキヤリア輸送物質とキヤリア発
生物質とを含有し、当該キヤリア発生物質が前記
一般式〔〕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。 5 前記感光層が前記一般式〔〕で表されるア
ゾ化合物であるキヤリア発生物質を含有するキヤ
リア発生層とキヤリア輸送物質を含有するキヤリ
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。[Scope of Claims] 1. An electrophotographic photoreceptor comprising a photosensitive layer containing at least one azo compound represented by the following general formula [] on a conductive support. General formula [] (In the formula, R 1 and R 2 represent a hydrogen atom, a halogen atom, an alkyl group, or an alkoxy group, A represents a coupler residue having a phenolic hydroxyl group, X is an oxygen atom or a sulfur atom, and Y is a direct bond or Represents a vinylene group. Also, m and n represent 0 or 1, but at least one of m and n shall not be 0.) 2 In the patent claim in which X in the above general formula [] is a sulfur atom. The electrophotographic photoreceptor according to scope 1. 3 A in the above general formula [] is the following general formula []
An electrophotographic photoreceptor according to claim 1, which is represented by ~ [ ]. General formula [] General formula [] General formula [] General formula [] General formula [] (In the formula, R 3 , R 4 and R 5 are a hydrogen atom, a substituted or unsubstituted alkyl group, an aralkyl group or an aryl group; Z is a substituted or unsubstituted divalent group of an aromatic hydrocarbon or a nitrogen atom in the ring) 4. A patent in which the photosensitive layer contains a carrier transporting substance and a carrier generating substance, and the carrier generating substance is an azo compound represented by the general formula []. An electrophotographic photoreceptor according to claim 1. 5 Claims in which the photosensitive layer is constituted by a laminate of a carrier generating layer containing a carrier generating substance which is an azo compound represented by the general formula [] and a carrier transporting layer containing a carrier transporting substance. 2. The electrophotographic photoreceptor according to item 1.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP25182886A JPS63106758A (en) | 1986-10-24 | 1986-10-24 | Electrophotographic sensitive body |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP25182886A JPS63106758A (en) | 1986-10-24 | 1986-10-24 | Electrophotographic sensitive body |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS63106758A JPS63106758A (en) | 1988-05-11 |
JPH0560861B2 true JPH0560861B2 (en) | 1993-09-03 |
Family
ID=17228525
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP25182886A Granted JPS63106758A (en) | 1986-10-24 | 1986-10-24 | Electrophotographic sensitive body |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS63106758A (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2006111961A (en) * | 2004-09-17 | 2006-04-27 | Nippon Seiki Co Ltd | Vapor deposition source system |
-
1986
- 1986-10-24 JP JP25182886A patent/JPS63106758A/en active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS63106758A (en) | 1988-05-11 |
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