JPH028251A - Purification of polycyclic quinone pigment by sublimation and photoreceptor for electrophotography containing the same pigment - Google Patents
Purification of polycyclic quinone pigment by sublimation and photoreceptor for electrophotography containing the same pigmentInfo
- Publication number
- JPH028251A JPH028251A JP16018788A JP16018788A JPH028251A JP H028251 A JPH028251 A JP H028251A JP 16018788 A JP16018788 A JP 16018788A JP 16018788 A JP16018788 A JP 16018788A JP H028251 A JPH028251 A JP H028251A
- Authority
- JP
- Japan
- Prior art keywords
- group
- sublimation
- pigment
- polycyclic quinone
- substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 title claims abstract description 67
- 239000000049 pigment Substances 0.000 title claims abstract description 56
- 238000000859 sublimation Methods 0.000 title claims abstract description 39
- 230000008022 sublimation Effects 0.000 title claims abstract description 39
- 125000003367 polycyclic group Chemical group 0.000 title claims abstract description 32
- 108091008695 photoreceptors Proteins 0.000 title claims abstract description 22
- 238000000746 purification Methods 0.000 title claims abstract description 16
- 239000002994 raw material Substances 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims description 16
- 230000035945 sensitivity Effects 0.000 abstract description 12
- 238000011084 recovery Methods 0.000 abstract description 7
- 230000003595 spectral effect Effects 0.000 abstract description 6
- 239000010410 layer Substances 0.000 description 53
- 125000003118 aryl group Chemical group 0.000 description 24
- 125000000217 alkyl group Chemical group 0.000 description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 13
- 239000000126 substance Substances 0.000 description 11
- 125000005843 halogen group Chemical group 0.000 description 10
- 125000003545 alkoxy group Chemical group 0.000 description 9
- 125000003710 aryl alkyl group Chemical group 0.000 description 8
- 239000011230 binding agent Substances 0.000 description 7
- 125000003277 amino group Chemical group 0.000 description 6
- 125000000623 heterocyclic group Chemical group 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- -1 polycyclic quinone compound Chemical class 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZTWQZJLUUZHJGS-UHFFFAOYSA-N Vat Yellow 4 Chemical compound C12=CC=CC=C2C(=O)C2=CC=C3C4=CC=CC=C4C(=O)C4=C3C2=C1C=C4 ZTWQZJLUUZHJGS-UHFFFAOYSA-N 0.000 description 3
- 239000012790 adhesive layer Substances 0.000 description 3
- 230000004888 barrier function Effects 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 229920000180 alkyd Polymers 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 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 2
- 125000000732 arylene group Chemical group 0.000 description 2
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000002612 dispersion medium Substances 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 229910002804 graphite Inorganic materials 0.000 description 2
- 239000010439 graphite Substances 0.000 description 2
- 229920006158 high molecular weight polymer Polymers 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 2
- LLBIOIRWAYBCKK-UHFFFAOYSA-N pyranthrene-8,16-dione Chemical compound C12=CC=CC=C2C(=O)C2=CC=C3C=C4C5=CC=CC=C5C(=O)C5=C4C4=C3C2=C1C=C4C=C5 LLBIOIRWAYBCKK-UHFFFAOYSA-N 0.000 description 2
- 150000003219 pyrazolines Chemical class 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- KNKRKFALVUDBJE-UHFFFAOYSA-N 1,2-dichloropropane Chemical compound CC(Cl)CCl KNKRKFALVUDBJE-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
- WPMHMYHJGDAHKX-UHFFFAOYSA-N 1-ethenylpyrene Chemical compound C1=C2C(C=C)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 WPMHMYHJGDAHKX-UHFFFAOYSA-N 0.000 description 1
- BIEFDNUEROKZRA-UHFFFAOYSA-N 2-(2-phenylethenyl)aniline Chemical class NC1=CC=CC=C1C=CC1=CC=CC=C1 BIEFDNUEROKZRA-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 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
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 108010023321 Factor VII Proteins 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004419 Panlite Substances 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 229920002433 Vinyl chloride-vinyl acetate copolymer Polymers 0.000 description 1
- NFGODEMQGQNUKK-UHFFFAOYSA-M [6-(diethylamino)-9-(2-octadecoxycarbonylphenyl)xanthen-3-ylidene]-diethylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCCOC(=O)C1=CC=CC=C1C1=C2C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C21 NFGODEMQGQNUKK-UHFFFAOYSA-M 0.000 description 1
- 125000000641 acridinyl group Chemical class C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- KCNKJCHARANTIP-SNAWJCMRSA-N allyl-{4-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-but-2-enyl}-methyl-amine Chemical compound C=1OC2=CC(OC/C=C/CN(CC=C)C)=CC=C2C=1C1=CC=C(Br)C=C1 KCNKJCHARANTIP-SNAWJCMRSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 description 1
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 1
- 229940027998 antiseptic and disinfectant acridine derivative Drugs 0.000 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 238000007611 bar coating method Methods 0.000 description 1
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000002800 charge carrier Substances 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- QJNYIFMVIUOUSU-UHFFFAOYSA-N chloroethene;ethenyl acetate;furan-2,5-dione Chemical compound ClC=C.CC(=O)OC=C.O=C1OC(=O)C=C1 QJNYIFMVIUOUSU-UHFFFAOYSA-N 0.000 description 1
- 229920006026 co-polymeric resin Polymers 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 150000001907 coumarones Chemical class 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000007606 doctor blade method Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 150000002461 imidazolidines 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
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 229940102253 isopropanolamine Drugs 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 150000007978 oxazole derivatives Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000001791 phenazinyl group Chemical class C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- WPPDXAHGCGPUPK-UHFFFAOYSA-N red 2 Chemical compound C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=2C=3C4=CC=C5C6=CC=C7C8=C(C=9C=CC=CC=9)C9=CC=CC=C9C(C=9C=CC=CC=9)=C8C8=CC=C(C6=C87)C(C=35)=CC=2)C4=C1C1=CC=CC=C1 WPPDXAHGCGPUPK-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 150000007979 thiazole derivatives Chemical class 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Photoreceptors In Electrophotography (AREA)
Abstract
Description
【発明の詳細な説明】
[産業上の利用分野]
本発明は多環午ノン系顔料の昇華精製方法、並びに多環
キノン系顔料を含む電子写真感光体に関するものである
。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a sublimation purification method for a polycyclic quinone pigment, and an electrophotographic photoreceptor containing the polycyclic quinone pigment.
[従来技術]
電子写真感光体は一般に電子写真複写機、プリンター等
に広く用いられているが、その用途に応じて電子写真感
光体に要求される特性も異なるものである。例えば電子
写真複写機、特に事務用複写機においては、黒ならびに
青系統の原稿の複写画像再現性と共に赤色画像(例えば
赤色の印かんの文字、アンダーラインなど)の複写画像
再現性が重要視される。これらの複写画像再現性を達成
するためには、450ni 〜600nm (長くて
620nm )に電子写真感光体の分光感度を充分布し
ていることが望まれる。電子写真感光体の分光感度が6
60rvや700nl付近までのびると上記の赤色画像
の複写再現性が劣り、事務用複写機としては好ましくな
い。このため、通常のアゾ系顔料、特にジスアゾ系顔料
やトリスアゾ系顔料を電荷発生物質として用いた電子写
真感光体では、分光感度が700nm付近までのびるの
で、620〜630nm以上の波長の光をフィルターで
カットし、赤色感度を低下させて使用している。しかし
、このようなフィルターを用いると赤色感度のみでなく
、短波長感度も低下し、全体的に感度が低下してしまう
という欠点を有する。さらに、このようなアゾ系顔料を
電荷発生物質として用いた場合、その電化輸送能の低さ
から電荷発生層の膜厚を0.1〜0.3μm程度の薄膜
で形成する必要があり、このような?l膜を一般的な製
造方法である浸漬塗布法によって塗布すると、段ムラ、
液ダレ、凝集などの塗布欠陥を生じやすく、収率低下、
コストアップにつながっていた。[Prior Art] Electrophotographic photoreceptors are generally widely used in electrophotographic copying machines, printers, etc., but the characteristics required of the electrophotographic photoreceptors differ depending on the use. For example, in electrophotographic copying machines, especially office copying machines, importance is placed on the reproducibility of red images (for example, red stamp characters, underlines, etc.) as well as the reproducibility of black and blue originals. Ru. In order to achieve these types of copy image reproducibility, it is desirable that the spectral sensitivity of the electrophotographic photoreceptor be well distributed in the range of 450 ni to 600 nm (620 nm at the longest). The spectral sensitivity of the electrophotographic photoreceptor is 6
If it extends to around 60 rv or 700 nl, the reproduction reproducibility of the above-mentioned red image will be poor, making it undesirable for office copying machines. For this reason, in electrophotographic photoreceptors that use ordinary azo pigments, especially disazo pigments and trisazo pigments, as charge-generating substances, the spectral sensitivity extends to around 700 nm, so light with wavelengths of 620 to 630 nm or more can be filtered out. It is cut and used with lower red sensitivity. However, when such a filter is used, not only the red sensitivity but also the short wavelength sensitivity decreases, resulting in a disadvantage that the overall sensitivity decreases. Furthermore, when such an azo pigment is used as a charge generating substance, it is necessary to form a charge generating layer with a thin film thickness of approximately 0.1 to 0.3 μm due to its low charge transport ability. like? When the film is applied using the dip coating method, which is a common manufacturing method, unevenness and
Coating defects such as dripping and agglomeration are likely to occur, resulting in lower yields and
This led to an increase in costs.
また、複写画像再現性の良好な顔料としては多環キノン
系顔料が知られている(特開昭57−67933号参照
)。多環キノン系顔料は450nlll〜570nn+
の領域に対して感度が高くzこのため赤色画像の複写再
現性が優れており、さらにアゾ系化合物やフタロシアニ
ン系化合物に比べ感度、帯電電位、残留電位などについ
ての繰り返し特性が著しく安定であるという特徴を有す
る。Furthermore, polycyclic quinone pigments are known as pigments with good copy image reproducibility (see JP-A-57-67933). Polycyclic quinone pigments are 450nllll to 570nn+
It has high sensitivity in the region of Has characteristics.
[発明が解決しようとする問題点]
ところで、ここに用いられる多環キノン系顔料は、市販
されているままのもの、独自に合成したもの、等が殆ど
である。しかしながら、斯かる多環キノン系顔料を電子
写真感光体の構成に用いた時には次のような問題がある
。[Problems to be Solved by the Invention] By the way, most of the polycyclic quinone pigments used here are those that are commercially available or those that have been independently synthesized. However, when such polycyclic quinone pigments are used in the construction of electrophotographic photoreceptors, the following problems arise.
すなわち上記のような多環キノン系顔料には、副生成物
、界面活性剤、無機塩類等の不純物が含まれているため
、生成した荷電キャリアがトラップされ、反復して多数
回の複写操作を行なった場合に残留電位が累積的に大き
くなり複写画像にカブリが発生するようになる。In other words, since the polycyclic quinone pigments mentioned above contain impurities such as by-products, surfactants, and inorganic salts, the generated charge carriers are trapped and cannot be repeatedly copied many times. If this is done, the residual potential will accumulate and fog will occur on the copied image.
この問題を解決するための方法どじで、多環キノン系顔
料が昇華性を有するという性質を利用して、昇華生成さ
れた多環キノン系顔料を用いる方法が、例えば特開昭5
7−67934号公報に記載されている。ところが従来
の昇華精製法では、必ずしも、精製時に昇華精製品の粉
体が飛散して回収率を上げることができなかったり、ま
た不純物が十分に除去されておらず純度を上げることが
できなかったので、電子写真特性において満足のいく結
果が得られなかった。In order to solve this problem, there is a method of using polycyclic quinone pigments produced by sublimation, taking advantage of the property that polycyclic quinone pigments have sublimation properties, for example, in Japanese Patent Application Laid-Open No.
It is described in Japanese Patent No. 7-67934. However, with conventional sublimation purification methods, it is not always possible to increase the recovery rate because the powder of the sublimation purified product scatters during purification, or impurities are not sufficiently removed and it is not possible to increase the purity. Therefore, satisfactory results in terms of electrophotographic properties could not be obtained.
このため、多環キノン系顔料を電荷発生物質として用い
た実際上充分良好な特性を有する電子写真感光体が今ま
で望まれていた。For this reason, there has been a desire for an electrophotographic photoreceptor that uses a polycyclic quinone pigment as a charge generating substance and has sufficiently good characteristics in practice.
本発明は上記従来の問題点に鑑みなされたものであり、
第1に純度の高い多環キノン系顔料を効率良く得るため
の昇華精製方法を提供すること、第2に電子写真複写機
、プリンター等に適した分光感度特性を有しかつ電子写
真特性の優れた電子写真感光体を提供することを目的と
する。The present invention has been made in view of the above conventional problems,
Firstly, it provides a sublimation purification method for efficiently obtaining a highly pure polycyclic quinone pigment, and secondly, it has spectral sensitivity characteristics suitable for electrophotographic copying machines, printers, etc., and has excellent electrophotographic characteristics. The purpose of the present invention is to provide an electrophotographic photoreceptor that has the following characteristics.
[問題を解決するための手段]
本発明の昇華精製方法は昇華時の真空度6×10’To
rr以下、かつ、昇華時の原料温度350〜410℃で
多環キノン系顔料を昇華精製することを特徴としている
。また本発明の電子写真感光体は、かかる方法により昇
華精製された多環キノン系顔料を感光層に含有すること
を特徴としている。[Means for solving the problem] The sublimation purification method of the present invention uses a vacuum degree of 6×10'To during sublimation.
It is characterized in that polycyclic quinone pigments are purified by sublimation at a temperature below rr and at a raw material temperature of 350 to 410°C during sublimation. Further, the electrophotographic photoreceptor of the present invention is characterized in that the photosensitive layer contains a polycyclic quinone pigment purified by sublimation by such a method.
本発明に係る多環キノン系顔料の昇華M製方法について
述べる。第1図は本発明の昇華精製方法を実施するため
に用いられる具体的な装置の一例を示す断面図である。The method for producing M by sublimation of polycyclic quinone pigments according to the present invention will be described. FIG. 1 is a sectional view showing an example of a specific apparatus used to carry out the sublimation purification method of the present invention.
本発明に用いられる昇華精製装置は第1図に示されてい
るように真空装置(1)の内部に回収板(2)、昇華ボ
ート(3)及びヒータ(5)を有してなる。ここでいう
昇華ボート(3)とは原料(4)を入れて蒸発させるた
めのものであり、例えばグラファイト等でできている。As shown in FIG. 1, the sublimation purification apparatus used in the present invention includes a recovery plate (2), a sublimation boat (3), and a heater (5) inside a vacuum apparatus (1). The sublimation boat (3) mentioned here is for putting the raw material (4) in and evaporating it, and is made of, for example, graphite.
回収板(2)は昇華ボートを置いた台(7)にネジ等で
取り付けられており、昇華精製後はとりはずして精製顔
料を回収することができるようになっている。真空装置
(1)には真空度モニター(6)が取り付けられており
、真空度を調節できるようになっている。ヒーター(5
)は原料(4)の上部の位置に取りつけられており、原
料(4)を所定の温度範囲となるように加熱する。The recovery plate (2) is attached with screws or the like to the stand (7) on which the sublimation boat is placed, and can be removed after sublimation purification to recover the purified pigment. A vacuum level monitor (6) is attached to the vacuum device (1) so that the vacuum level can be adjusted. Heater (5
) is attached above the raw material (4) and heats the raw material (4) to a predetermined temperature range.
また、上記の昇華精製装置において昇華ボート(3)に
は、原料を覆うような形で網が設置されていることが好
ましく、更に好ましくは、その網が30〜400メツシ
ユの網であることである。Further, in the above-mentioned sublimation purification apparatus, it is preferable that a net is installed in the sublimation boat (3) so as to cover the raw material, and more preferably, the net has a mesh size of 30 to 400. be.
かかる構成の装置を用いて、昇華時の原料温度350〜
410℃、かつ、昇華時の真空度6X10−4T or
r以下という条件で、多環キノン系顔料の昇華精製を行
なうことにより、純度の高い多環キノン系顔料を高収率
で得ることができる。Using an apparatus with such a configuration, the raw material temperature during sublimation is 350~
410℃ and degree of vacuum during sublimation 6X10-4T or
By performing sublimation purification of a polycyclic quinone pigment under the condition of r or less, a highly pure polycyclic quinone pigment can be obtained in high yield.
本発明に用いられる多環キノン系顔料としては下記−数
式[A]で示されるアントアントロン系顔料、下記−数
式[8コで示されるジベンズピレンキノン系顔料及び下
記−数式[CIで示されるピラントロン系顔料から選ば
れる少なくとも一種を挙げることができる。Examples of the polycyclic quinone pigments used in the present invention include an anthrone pigment represented by the following formula [A], a dibenzpyrenequinone pigment represented by the following formula [8], and a dibenzpyrene quinone pigment represented by the following formula [CI]. At least one selected from pyranthrone pigments can be mentioned.
一般式[A]
一般式[B]
式中、Xはハロゲン原子、ニトロ基、シアムLアシル基
又はカルボキシル基を表わし、nは0〜4の整数を表わ
し、mは0〜6の整数を表わす。General formula [A] General formula [B] In the formula, X represents a halogen atom, a nitro group, a cyam L acyl group, or a carboxyl group, n represents an integer of 0 to 4, and m represents an integer of 0 to 6. .
−数式[A]で示されるアンドアントロン系顔料の具体
的化合物を挙げると次の通りである。- Specific compounds of the andanthrone pigment represented by formula [A] are as follows.
−数式[CI
[Al1
[A21
[A91
[A3]
[A4]
[A10]
[A5]
[Ac1
[A11]
[A71
[A8]
一般式[81で示されるジベンズピレンキノン系顔料の
具体的化合物例を挙げると次の通りである。-Specific compound examples of dibenzpyrenequinone pigments represented by formula [CI [Al1 [A21 [A91] [A3] [A4] [A10] [A5] [Ac1 [A11] [A71 [A8] General formula [81] The following are examples.
[B1】 [B51 ○ [B2〕 [B11 [B3] [B71 [B41 [B81 [B11 [C1] 一般式[C] で示されるピラントロン系顔料の [C2〕 具体的化合物例を挙げると次の通りである。[B1] [B51 ○ [B2] [B11 [B3] [B71 [B41 [B81 [B11 [C1] General formula [C] of the pyranthrone pigment shown in [C2] Specific examples of compounds are as follows.
[C31
[C4]
[C7]
[C51
[C81
[C61
【C9]
以上の如き多環キノン系顔料は公知の方法により合成す
ることができるが、市販品として入手することもできる
。[C31 [C4] [C7] [C51 [C81 [C61] [C9] The polycyclic quinone pigments described above can be synthesized by known methods, but can also be obtained as commercial products.
電子写真感光体の構成は種々の形態が知られているが、
本発明の電子写真感光体はそれらのいずれの形態をもと
り得る。Various configurations of electrophotographic photoreceptors are known, but
The electrophotographic photoreceptor of the present invention can take any of these forms.
通常は、第2図〜第7図の形態である。第2図及び第3
図では、導電性支持体8上に前述の多環キノン系顔料を
含有する電荷発生層9と、後述する電荷輸送物質を主成
分として含有する電荷輸送層10との積層体より成る感
光層11を設けており、第2図と第3図では、電荷発生
B9と電荷輸送層10の積層順が異なる。第4図及び第
5図に示すようにこの感光層11は、導電性支持体上に
、接着層、バリア層などの中間層12を介して設けても
よい。このように感光層11を二層構成としたときに最
も優れた電子写真特性を有する感光体が得られる。また
本発明においては、第6図および第7因に示すように前
記多環キノン系顔料を電荷輸送物質を含有する層13中
に分散せしめて成る感光層11を導電性支持体8上に直
接、あるいは中間層12を介して設けてもよい。また本
発明においては、最外層として保r!1層を設けてもよ
い。Usually, the configuration is as shown in FIGS. 2 to 7. Figures 2 and 3
In the figure, a photosensitive layer 11 consisting of a laminate of a charge generation layer 9 containing the above-mentioned polycyclic quinone pigment on a conductive support 8 and a charge transport layer 10 containing as a main component a charge transport substance to be described later. 2 and 3, the stacking order of the charge generation B9 and the charge transport layer 10 is different. As shown in FIGS. 4 and 5, this photosensitive layer 11 may be provided on a conductive support with an intermediate layer 12 such as an adhesive layer or a barrier layer interposed therebetween. When the photosensitive layer 11 has a two-layer structure in this manner, a photoreceptor having the most excellent electrophotographic properties can be obtained. Further, in the present invention, as shown in FIG. 6 and factor 7, a photosensitive layer 11 formed by dispersing the polycyclic quinone pigment in a layer 13 containing a charge transport substance is directly deposited on the conductive support 8. Alternatively, it may be provided via the intermediate layer 12. In addition, in the present invention, the outermost layer contains r! One layer may be provided.
二層構成の感光層11を構成する電荷発生層9は導電性
支持体8、もしくは電荷輸送層10上に直接、あるいは
必要に応じて接着層もしくはバリヤ層などの中間層12
を設けた上に例えば次の方法によって形成することがで
きる。The charge generation layer 9 constituting the two-layer photosensitive layer 11 is applied directly to the conductive support 8 or the charge transport layer 10, or if necessary, to an intermediate layer 12 such as an adhesive layer or a barrier layer.
It can be formed, for example, by the following method.
M−1)多環キノン系顔料を適当な溶媒に溶解した溶液
を、あるいは必要に応じてバインダー樹脂を加え混合溶
解した溶液を塗布する方法。M-1) A method of applying a solution in which a polycyclic quinone pigment is dissolved in a suitable solvent, or a solution in which a binder resin is added and mixed as necessary.
M−2)多環キノン系化合物をボールミル、ホモミキサ
等によって分散媒中で微細粒子(好ましくは粒径5μm
以下、更に好ましくは1μm以下)とし、必要に応じて
バインダー樹脂を加え混合分散した分散液を塗布する方
法。M-2) The polycyclic quinone compound is pulverized into fine particles (preferably with a particle size of 5 μm) in a dispersion medium using a ball mill, homomixer, etc.
(hereinafter, more preferably 1 μm or less), and a method in which a binder resin is added and mixed and dispersed as necessary, and a dispersion is applied.
また、この多環キノン系顔料は他の電荷発生物質と併用
して電荷発生層を形成してもよい。Further, this polycyclic quinone pigment may be used in combination with other charge generating substances to form a charge generating layer.
電荷発生層の形成に使用される溶媒あるいは分散媒とし
ては、n−ブチルアミン、ジエチルアミン、エチレンジ
アミン、イソプロパツールアミン、トリエタノールアミ
ン、トリエチレンジアミン、N、N−ジメチルホルムア
ミド、アセトン、メチルエチルケトン、シクロヘキサノ
ン、ベンゼン、トルエン、キシレン、クロロホルム、1
.2−ジクロロエタン、1.2−ジクロロプロパン、1
゜1.2−トリクロロエタン、1,1.1−トリクロロ
エタン、トリクロロエチレン、テトラクロロエタン、ジ
クロロメタン、テトラヒドロフラン、ジオキサン、メタ
ノール、エタノール、イソプロパツール、酢酸エチル、
酢酸ブチル、ジメチルスルホキシド、メチルセロソルブ
等が挙げられる。Examples of the solvent or dispersion medium used for forming the charge generation layer include n-butylamine, diethylamine, ethylenediamine, isopropanolamine, triethanolamine, triethylenediamine, N,N-dimethylformamide, acetone, methylethylketone, cyclohexanone, and benzene. , toluene, xylene, chloroform, 1
.. 2-dichloroethane, 1,2-dichloropropane, 1
゜1.2-trichloroethane, 1,1.1-trichloroethane, trichloroethylene, tetrachloroethane, dichloromethane, tetrahydrofuran, dioxane, methanol, ethanol, isopropanol, ethyl acetate,
Examples include butyl acetate, dimethyl sulfoxide, methyl cellosolve, and the like.
また、電荷輸送層は上記電荷発生層と同様にして形成す
ることができる。Further, the charge transport layer can be formed in the same manner as the charge generation layer described above.
電荷発生層あるいは電荷輸送層の形成に用いられるバイ
ンダー樹脂は任意のものを用いることができるが、疎水
性で、かつy、電率が高く、電気絶縁性のフィルム形成
性高分子重合体を用いるのが好ましい。このような高分
子重合体としては、例えば次のものを挙げることができ
るが、これらに限定されるものではない。Any binder resin can be used to form the charge generation layer or the charge transport layer, but a film-forming polymer that is hydrophobic, has high electric conductivity, and is electrically insulating is used. is preferable. Examples of such high molecular weight polymers include, but are not limited to, the following.
P−1)ポリカーボネート
P−2)ポリエステル
P−3)メタクリル酸
P−4)アクリル樹脂
P−5)ポリ塩化ビニル
P−6)ポリ塩化ビニリデン
P−7)ポリスチレン
P−8)ポリビニルアセテート
P−9)スチレン−ブタジェン共重合体p −io)塩
化ビニリデン−アクリロニトリル共重合体
p −11)塩化ビニル−酢酸ビニル共重合体p−12
)塩化ビニル−酢酸ビニル−無水マレイン酸共重合体
p −13)シリコン樹脂
p −14)シリコン−アルキッド樹脂p−15)フェ
ノールホルムアルデヒド樹脂P −16)スチレン−ア
ルキッド樹脂p −17)ポリ−N−ビニルカルバゾー
ルp − 18)ポリビニルブチラール
p − 19)ポリビニルフォルマールこれらのバイン
ダー樹脂は、単独であるいは2種以上の混合物として用
いることができる。P-1) Polycarbonate P-2) Polyester P-3) Methacrylic acid P-4) Acrylic resin P-5) Polyvinyl chloride P-6) Polyvinylidene chloride P-7) Polystyrene P-8) Polyvinyl acetate P-9 ) Styrene-butadiene copolymer p -io) Vinylidene chloride-acrylonitrile copolymer p-11) Vinyl chloride-vinyl acetate copolymer p-12
) Vinyl chloride-vinyl acetate-maleic anhydride copolymer p-13) Silicone resin p-14) Silicone-alkyd resin p-15) Phenol formaldehyde resin P-16) Styrene-alkyd resin p-17) Poly-N- Vinyl carbazole p-18) Polyvinyl butyral p-19) Polyvinyl formal These binder resins can be used alone or as a mixture of two or more.
以上のようにして形成される電荷発生層において、多環
キノン系顔料とバインダーとの重量比は好ましくは10
0:O〜1000である。電荷発生物質の含有割合がこ
れより少ないと光感度が低く、残留電位の増加を招き、
またこれより多いと暗減衰及び受容電位が低下する。In the charge generation layer formed as described above, the weight ratio of the polycyclic quinone pigment to the binder is preferably 10.
0:0 to 1000. If the content of the charge generating substance is less than this, the photosensitivity will be low and the residual potential will increase.
Moreover, if the amount is more than this, dark decay and acceptance potential decrease.
形成される電荷発生層の膜厚は、好ましくは0、01
〜10μmである。The thickness of the charge generation layer to be formed is preferably 0.01.
~10 μm.
また、前記のようにして形成される電荷輸送層において
、電荷輸送物質は電荷輸送層中のバインダー樹脂100
重量部当り20〜200重凹部が好ましく、特に好まし
くは30〜150fi ffi部である。Further, in the charge transport layer formed as described above, the charge transport material is the binder resin 100 in the charge transport layer.
It is preferably 20 to 200 parts by weight, particularly preferably 30 to 150 parts by weight.
また、形成される電荷輸送層の厚さは、好ましくは5〜
50μm1特に好ましくは5〜30μmである。Further, the thickness of the charge transport layer to be formed is preferably 5 to 5.
50 μm, particularly preferably 5 to 30 μm.
本発明で使用する電荷輸送物質は、カルバゾール誘導体
、オキサゾール誘導体、オキサジアゾール誘導体、チア
ゾール誘導体、チアジアゾール誘導体、トリアゾール誘
導体、イミダゾール誘導体、イミダシロン誘導体、イミ
ダゾリジン誘導体、ビスイミダゾリジン誘導体、スチリ
ル化合物、ヒドラゾン化合物、ピラゾリン誘導体、オキ
サシロン誘導体、ベンゾチアゾール誘導体、ベンズイミ
ダゾール誘導体、キナゾリン誘導体、ベンゾフラン誘導
体、アクリジン誘導体、フェナジン誘導体、アミノスチ
ルベン誘導体、トリアリールアミン誘導体、フェニレン
ジアミン誘導体、スチルベン誘導体、ポリ−N−ビニル
カルバゾール、ポリ−1−ビニルピレン、ポリ−9−ご
ニルアントラセン等から選ばれた一種又は二種以上であ
ってよい。The charge transport substances used in the present invention include carbazole derivatives, oxazole derivatives, oxadiazole derivatives, thiazole derivatives, thiadiazole derivatives, triazole derivatives, imidazole derivatives, imidasilone derivatives, imidazolidine derivatives, bisimidazolidine derivatives, styryl compounds, and hydrazone compounds. , pyrazoline derivatives, oxacilone derivatives, benzothiazole derivatives, benzimidazole derivatives, quinazoline derivatives, benzofuran derivatives, acridine derivatives, phenazine derivatives, aminostilbene derivatives, triarylamine derivatives, phenylenediamine derivatives, stilbene derivatives, poly-N-vinylcarbazole, It may be one or more selected from poly-1-vinylpyrene, poly-9-nylanthracene, and the like.
かかる電荷輸送物質の具体的化合物例は特願昭61−1
95881号明細書に記載されている。以下にその一般
式を掲げる。Specific examples of such charge-transporting substances are disclosed in Japanese Patent Application No. 61-1.
No. 95881. The general formula is listed below.
電荷輸送物質とし℃の次の一般式[I]又は[I[]の
スチリル化合物が使用可能である。As a charge transport material, a styryl compound having the following general formula [I] or [I[] can be used.
一般式[工1:
(但、この一般式中、
R’ R2:i!置換若くは未置換のアルキル基、ア
リール基を表わし、置換基としてはアルキル基、アルコ
キシ基、置換アミノ基、水酸基、ハロゲン原子、アリー
ル基を用いる。General formula [Equation 1: (However, in this general formula, R' R2: i! represents a substituted or unsubstituted alkyl group or aryl group, and substituents include an alkyl group, an alkoxy group, a substituted amino group, a hydroxyl group, A halogen atom and an aryl group are used.
Ar’、Ar2:置換若しくは未置換のアリール基を表
わし、置換基としてはアルキル基、アルコキシ基、置換
アミLL水酸基、ハロゲン原子、アリール基を用いる。Ar', Ar2: represents a substituted or unsubstituted aryl group, and as a substituent, an alkyl group, an alkoxy group, a substituted AMI LL hydroxyl group, a halogen atom, or an aryl group is used.
R3R4:il置換若くは未置換のアリール基、水素原
子を表わし、置換基としてはアルキル基、アルコキシ基
、置換アミLL水酸基、ハロゲン原子、アリール基を用
いる。)
一般式[■]:
(但、この一般式中、
R5:置換若しくは未置換のアリール基、R6:水素原
子、ハロゲン原子、置換若しくは未置換のアルキル基、
アルコキシ基、アミン基、置換アミLL水M基、
R7、置換若しくは未置換のアリール基、置換若しくは
未置換の複素環基を表わす。)また、電荷輸送物質とし
て次の一般式[1]、[IV ]、[IVa ]、[I
Vb ] 又1.t [V] (7)ヒドラゾン化合物
も使用可能である
一般式[■]:
(但、この一般式中、
R8及びR9:それぞれ水素原子又はハロゲン原子、
RIO及びR11:それぞれ置換若しくは未置換のアリ
ール基、
Ar3 :@換若しくは未置換のアリーレン基を表わす
。)
一般式[■]:
(但、この一般式中、
R12:M換若しくは未置換のアリール基、置換若しく
は未置換のカルバゾリル基、又は置換若しくは未置換の
複素環基を表し、
R13R14及びR15:水素原子、アルキル基、置換
若しくは未置換のアリール基、又は置換若しくは未置換
のアラルキル基を表す。)
一般式[IVa]:
R”
(但、この一般式中、
R16:メチル基、エチル基、2−ヒドロキシエチル基
又は2−クロルエチル基、
R17:メチル基、エチル基、ベンジル基又はフェニル
基、
R18:メチル基、エチル基、ベンジル基又はフェニル
基を示す。)
一般式[IVbl
(但、この一般式中、R+9は置換若しくは未置換のナ
フチル基;R20は置換若しくは未置換のアルキル基、
アラルキル基又はアリールB 、 R2Fは水素原子、
アルキル基又はアルコキシB 、 R22及びR23は
置換若しくは未置換のアル4;ル基、アラルキル基又は
アリール基からなる互いに同一の若しくは異なる基を示
ず。)
一般式[V]:
(但、この−数式中、
R24:@換若しくは未置換のアリール基又は置換若し
くは未置換の複素環基、
R25:水素原子、置換若しくは未置換のアルキル基又
は置換若しくは未置換のアリール基、Q:水素原子、ハ
ロゲン原子、アルキル基、置換アミノ基、アルコキシ基
又はシアノ基、S:O又は1の整数を表す。)
また、電荷輸送物質として、次の一般式[VI]のピラ
ゾリン化合物も使用可能である。R3R4: il represents a substituted or unsubstituted aryl group or a hydrogen atom, and as a substituent, an alkyl group, an alkoxy group, a substituted amino LL hydroxyl group, a halogen atom, or an aryl group is used. ) General formula [■]: (However, in this general formula, R5: substituted or unsubstituted aryl group, R6: hydrogen atom, halogen atom, substituted or unsubstituted alkyl group,
It represents an alkoxy group, an amine group, a substituted amine LL water M group, R7, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group. ) In addition, the following general formulas [1], [IV], [IVa], [I
Vb ] Also 1. t [V] (7) A hydrazone compound can also be used General formula [■]: (However, in this general formula, R8 and R9: each a hydrogen atom or a halogen atom, RIO and R11: each a substituted or unsubstituted aryl group, Ar3: @represents a substituted or unsubstituted arylene group.) General formula [■]: (However, in this general formula, R12: M-substituted or unsubstituted aryl group, substituted or unsubstituted carbazolyl group, or Represents a substituted or unsubstituted heterocyclic group, R13R14 and R15: represents a hydrogen atom, an alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aralkyl group.) General formula [IVa]: R'' ( However, in this general formula, R16: methyl group, ethyl group, 2-hydroxyethyl group, or 2-chloroethyl group, R17: methyl group, ethyl group, benzyl group, or phenyl group, R18: methyl group, ethyl group, benzyl group or a phenyl group.) General formula [IVbl (However, in this general formula, R+9 is a substituted or unsubstituted naphthyl group; R20 is a substituted or unsubstituted alkyl group,
Aralkyl group or aryl B, R2F is a hydrogen atom,
The alkyl group or alkoxy B, R22 and R23 do not represent the same or different groups consisting of a substituted or unsubstituted alkyl group, aralkyl group or aryl group. ) General formula [V]: (However, in this formula, R24: @substituted or unsubstituted aryl group or substituted or unsubstituted heterocyclic group, R25: hydrogen atom, substituted or unsubstituted alkyl group, or substituted or unsubstituted heterocyclic group) (Unsubstituted aryl group, Q: hydrogen atom, halogen atom, alkyl group, substituted amino group, alkoxy group, or cyano group, S: O or an integer of 1) In addition, as a charge transport substance, the following general formula [ Pyrazoline compounds of VI] can also be used.
−数式[VI]:
(但、この−数式中、
ffi:O又は1、
R26及びR27:m+i若しくは未置換のアリール基
、
R28:置換若しくは未置換のアリール基、若しくは複
素環基、
R29及びR30:水素原子、炭素原子数1〜4のアル
キル基、又は置換若しくは未置換のアリール基若しくは
アラルキル基(但、R29及びR30は共に水素原子で
あることはなく、また前記lがOのときはR29は水素
原子ではない。)コ更に、次の一般式[VI]のアミン
誘導体も電荷輸送物質として使用できる。- Formula [VI]: (However, in this - formula, ffi: O or 1, R26 and R27: m+i or unsubstituted aryl group, R28: substituted or unsubstituted aryl group, or heterocyclic group, R29 and R30 : Hydrogen atom, alkyl group having 1 to 4 carbon atoms, or substituted or unsubstituted aryl group or aralkyl group (However, both R29 and R30 are not hydrogen atoms, and when the above l is O, R29 is not a hydrogen atom.) Furthermore, an amine derivative of the following general formula [VI] can also be used as a charge transport material.
一般式[V[]:
(但、この−数式中、
Ar4.Ar5:置換若しくは未置換のフェニル基を表
し、置換基としてはハロゲン原子、アルキル基、アルケ
ニル基、ニトロ基、アルコキシ基を用いる。General formula [V[]: (However, in this formula, Ar4.Ar5 represents a substituted or unsubstituted phenyl group, and a halogen atom, an alkyl group, an alkenyl group, a nitro group, or an alkoxy group is used as a substituent.
Ar6 :置換若しくは未置換のフェニル基、ナフチル
基、アントリル基、フルオレニル基、複素環基を表し、
置換基としてはアルキル基、アルコキシ基、ハロゲン原
子、水酸基、アリールオキシ基、アリール基、アミムL
ニトロ基、ピペリジノ基、モルホリノ基、ナフチル基、
アンスリル基及び置換アミノ基を用いる。但、置換アミ
ノ基の置換基としてアシル基、アルキル基、アリール基
、アラルキル基を用いる。)
更に、次の一般式[■]の化合物も電荷輸送物質として
使用できる。Ar6: represents a substituted or unsubstituted phenyl group, naphthyl group, anthryl group, fluorenyl group, heterocyclic group,
Substituents include alkyl groups, alkoxy groups, halogen atoms, hydroxyl groups, aryloxy groups, aryl groups, amimu L
Nitro group, piperidino group, morpholino group, naphthyl group,
Anthryl groups and substituted amino groups are used. However, an acyl group, an alkyl group, an aryl group, or an aralkyl group is used as a substituent for the substituted amino group. ) Furthermore, a compound of the following general formula [■] can also be used as a charge transport material.
一般式[■]:
(但、この−数式中、
A r 7 :置換又は未置換のアリーレン基を表し
、R31、R32、R33及びR34;置換若しくは未
置換のアルキル基、置換若しくは未置換のアリール基、
又は置換若しくは未置換のアラルキル基を表す。)
更に、次の一般式[IX]の化合物−b電荷輸送物質と
して使用できる。General formula [■]: (However, in this formula, A r 7 represents a substituted or unsubstituted arylene group, R31, R32, R33 and R34; substituted or unsubstituted alkyl group, substituted or unsubstituted aryl basis,
Or represents a substituted or unsubstituted aralkyl group. ) Furthermore, compound-b of the following general formula [IX] can be used as a charge transport substance.
一般式[IX]:
(但、この−数式中、R35、R36、R37及びR3
8は、それぞれ水素原子、置換若しくは未置換のアルギ
ル基、シクロアルキル基、アルケニル基、アリール基、
ベンジル基又はアラルキル基、R39及びR411は、
それぞれ水素原子、置換若しくは未置換の炭素原子数1
〜40のアルキル基、シクロアルキル基、アルケニル基
、シクロアルケニル基、アリール基又はアラルギルI(
fl、1.R”とR40とが共同して炭素原子数3〜1
0の飽和若しくは不飽和の炭化水素環を形成してもよい
。)R4+、R42、R43及びR44は、それぞれ水
素原子、ハロゲン原子、ヒドロキシル基、置換若しくは
未置換のアルギル基、シクロアルキル基、アルケニル基
、アリール基、アラルキル基、アルコキシ基、アミノ基
、アルキルアミノ基又はアリールアミノ基である。]
本発明の電子写真感光体に用いられる導電性支18体ど
しては、合金を含めた金属板、金属ドラムまたは導電性
ポリマー、酸化インジウム等の導電性化合物や合金を含
めたアルミニウム、パラジウム、金等の金nR層を塗布
、蒸着あるいはラミネートして、導電性化された紙、プ
ラスチックフィルム等が挙げられる。接着層あるいはバ
リヤ層などの中間層としては、前記バインダー樹脂とし
て用いられる高分子重合体のほか、ポリビニルアルコー
ル、エチルセルロ−ス
ロース
ニウムなどが用いられる。General formula [IX]: (However, in this formula, R35, R36, R37 and R3
8 is a hydrogen atom, a substituted or unsubstituted argyl group, a cycloalkyl group, an alkenyl group, an aryl group,
Benzyl group or aralkyl group, R39 and R411,
1 hydrogen atom, substituted or unsubstituted carbon atom, respectively
~40 alkyl, cycloalkyl, alkenyl, cycloalkenyl, aryl or aralgyl I (
fl, 1. R'' and R40 jointly have 3 to 1 carbon atoms
0 saturated or unsaturated hydrocarbon rings may be formed. ) R4+, R42, R43 and R44 are each a hydrogen atom, a halogen atom, a hydroxyl group, a substituted or unsubstituted argyl group, a cycloalkyl group, an alkenyl group, an aryl group, an aralkyl group, an alkoxy group, an amino group, an alkylamino group Or it is an arylamino group. ] The 18 conductive supports used in the electrophotographic photoreceptor of the present invention include metal plates including alloys, metal drums, conductive polymers, conductive compounds such as indium oxide, aluminum including alloys, palladium, etc. Examples include paper, plastic film, etc., made conductive by coating, vapor depositing, or laminating a gold nR layer such as gold. As an intermediate layer such as an adhesive layer or a barrier layer, in addition to the high molecular weight polymer used as the binder resin, polyvinyl alcohol, ethyl cellulose, and the like can be used.
[実施例]
次に実施例によって本発明を説明するが、これらによっ
て本発明が限定されるものではない。[Example] Next, the present invention will be explained with reference to Examples, but the present invention is not limited by these.
市販の多環キノン系顔料である4,10−ジブロムアン
トアントロン(Monolite Red 2 YI
C1社製 C. I 、 No.59300 ) L
第1 図ノ真空装置内に配置したグラファイト製の昇華
ボートに充填し、表−1に示した原料温度および真空度
で5分間昇華せしめ、昇華ボートの15cm上方に配置
した回収板上に沈着させ精製顔料試料No.1〜N0.
20を得た。4,10-dibromanthanthrone (Monolite Red 2 YI) is a commercially available polycyclic quinone pigment.
Manufactured by C1 company C. I, No. 59300) L
Fig. 1 Filled into a graphite sublimation boat placed in the vacuum device shown in Figure 1, sublimated for 5 minutes at the raw material temperature and vacuum degree shown in Table 1, and deposited on a collection plate placed 15 cm above the sublimation boat. Purified pigment sample No. 1~N0.
I got 20.
精製顔料試料N0.1〜No.20の重層を測定し、仕
込量に対する回収率を求めた。この結果は表−1に示す
。Purified pigment samples No. 1 to No. 20 layers were measured and the recovery rate relative to the amount charged was determined. The results are shown in Table-1.
次にかくして得られた精製顔料試料N0.1〜No.2
0の3gを1,2−ジクロロエタン10(hQ中に加え
て48時間ボールミルにより分散を行なって電荷発生層
形成用塗布液を得た。次にアルミニウムをポリエチレン
テレフタレートフィルムにラミネートした導電性支持体
上に厚さ0.1μmの塩化ビニル−酢酸ビニル−無水マ
レイン酸共重合体樹脂より成る中間層を設け、前記電荷
発生層形成用塗布液をワイヤーバー塗布法により前記中
間層上に塗布して厚さ1ミクロンの電荷発生層を形成し
た。Next, the thus obtained purified pigment samples No. 1 to No. 2
3 g of 0 was added to 1,2-dichloroethane 10 (hQ) and dispersed in a ball mill for 48 hours to obtain a coating solution for forming a charge generation layer. Next, a coating solution for forming a charge generation layer was obtained. An intermediate layer made of a vinyl chloride-vinyl acetate-maleic anhydride copolymer resin having a thickness of 0.1 μm is provided on the substrate, and the charge generation layer forming coating liquid is applied onto the intermediate layer by a wire bar coating method to obtain a thickness of 0.1 μm. A charge generation layer having a thickness of 1 micron was formed.
一方、4−メチル−4” −(p−クロロスチリル〉ト
リフェニルアミン10oと2.4.6−ドリニトロー1
−クロルベンゼン0. 0111とポリカーボネート樹
脂「パンライトl−1250J (量大化成社製)
1 3Q トtr 1 、 2−シフCJ)Ltエタ>
1001flの溶剤中に溶解せしめ、ここに得られた
電荷輸送層をドクターブレード塗布法により前記電荷発
生層上に塗布し、温度80℃で1時間乾燥させて厚さ1
4μmの電荷輸送層を形成し、電子写真感光体試F4N
o.1〜20(感光体試料No.は精製顔料試料No.
と一致している)を作製した。On the other hand, 4-methyl-4''-(p-chlorostyryl>triphenylamine 10o and 2,4,6-dolinitro 1
-Chlorbenzene 0. 0111 and polycarbonate resin “Panlite l-1250J (manufactured by Ryotaikasei Co., Ltd.)”
1 3Q tr 1, 2-Schiff CJ) Lt eta>
The charge transport layer obtained was dissolved in 1001 fl of a solvent, and the resulting charge transport layer was applied onto the charge generation layer using a doctor blade coating method, and dried at a temperature of 80° C. for 1 hour to form a layer with a thickness of 1.
A charge transport layer of 4 μm was formed, and an electrophotographic photoreceptor sample F4N was formed.
o. 1 to 20 (Photoreceptor sample No. is purified pigment sample No.
) was created.
このようにして得られた電子写真感光体をエレクトロメ
ーターr S P − 428型」 (川口?i機製作
所製)に装着し、帯電器放電極に対する印加電圧を一6
KVとして5秒間帯電操作を行ない、この帯電操作直後
における感光層表面の帯i!電位V。The electrophotographic photoreceptor thus obtained was mounted on an electrometer RSP-428 type (manufactured by Kawaguchi-i Kiki Seisakusho), and the voltage applied to the charger discharge electrode was set to 16.
Charging operation was performed for 5 seconds as KV, and the band i! on the surface of the photosensitive layer immediately after this charging operation was performed. Potential V.
(V)と、この帯電を終了した後5秒後の値■1から初
期値Voに対する暗減衰の暗減衰率(DD)と、その後
の光照射により帯電電位が500Vがら50Vまで減衰
するのに必要な照射光IEr( lux − see
)とを測定した。その結果を表−1表−1かられかるよ
うに、本発明の試料は精製顔料の回収率も良く、さらに
暗減衰、感度等の電子写真特性も良い値を示している。(V), the value 5 seconds after this charging is finished, the dark decay rate (DD) of dark decay from 1 to the initial value Vo, and the charge potential attenuating from 500V to 50V due to subsequent light irradiation. Necessary irradiation light IEr (lux-see
) was measured. The results are shown in Table 1. As can be seen from Table 1, the samples of the present invention have a good recovery rate of purified pigment and also exhibit good electrophotographic properties such as dark decay and sensitivity.
これに対し、比較の試料では、純度の高い精製顔料を効
率良く得ることができず、さらに電子写真特性の結果も
満足のいくものではない。On the other hand, in the comparative samples, it was not possible to efficiently obtain purified pigments with high purity, and the results of electrophotographic properties were also not satisfactory.
[発明の効果コ
以上詳細に述べたように、本発明により電子写真複写機
、プリンター等に適した分光感度特性を有し、かつ電子
写真特性の優れた電子写真感光体を提供することができ
た。また、そのために必要とされる純度の高い多環キノ
ン系顔料を効率良く得るための昇華精製方法についての
検討もなされ、浪好な結果が得られた。[Effects of the Invention] As described in detail above, the present invention makes it possible to provide an electrophotographic photoreceptor that has spectral sensitivity characteristics suitable for electrophotographic copying machines, printers, etc., and has excellent electrophotographic characteristics. Ta. In addition, a sublimation purification method for efficiently obtaining the highly pure polycyclic quinone pigments required for this purpose was investigated, and favorable results were obtained.
第1図は本発明に係る昇華精製方法を実施するために用
いられる具体的な装置の一例を示す断面図である。
第2図〜第7図は、それぞれ本発明の感光体の構成例に
ついて示す断面図である。
1・・・真空装置 2・・・回収板3・・・昇華ボ
ート 4・・・原料
5・・・ヒーター 6・・・真空度モニター7・・
・台 8・・・導電性支持体9・・・電荷発
生層 10・・・電荷輸送層11・・・感光層 1
2・・・中間層13・・・電荷輸送物質を特徴するFIG. 1 is a sectional view showing an example of a specific apparatus used to carry out the sublimation purification method according to the present invention. FIGS. 2 to 7 are cross-sectional views respectively showing structural examples of the photoreceptor of the present invention. 1... Vacuum device 2... Recovery plate 3... Sublimation boat 4... Raw material 5... Heater 6... Vacuum level monitor 7...
- Stand 8... Conductive support 9... Charge generation layer 10... Charge transport layer 11... Photosensitive layer 1
2... Intermediate layer 13... Features a charge transport material
Claims (2)
昇華時の原料温度を350〜410℃とし、かつ、昇華
時の真空度を6×10^−^4Torr以下とすること
を特徴とする多環キノン系顔料の昇華精製方法。(1) In a method for sublimation purification of polycyclic quinone pigments,
A sublimation purification method for polycyclic quinone pigments, characterized in that the raw material temperature during sublimation is 350 to 410°C, and the degree of vacuum during sublimation is 6 x 10^-^4 Torr or less.
時の真空度6×10^−^4Torr以下で昇華精製さ
れた多環キノン系顔料を感光層に含有することを特徴と
する多環キノン系顔料を含有する電子写真感光体。(2) A polycyclic quinone pigment characterized in that the photosensitive layer contains a polycyclic quinone pigment purified by sublimation at a raw material temperature of 350 to 410°C during sublimation and a vacuum level of 6 x 10^-^4 Torr or less during sublimation. An electrophotographic photoreceptor containing a ring quinone pigment.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP16018788A JPH028251A (en) | 1988-06-28 | 1988-06-28 | Purification of polycyclic quinone pigment by sublimation and photoreceptor for electrophotography containing the same pigment |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP16018788A JPH028251A (en) | 1988-06-28 | 1988-06-28 | Purification of polycyclic quinone pigment by sublimation and photoreceptor for electrophotography containing the same pigment |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH028251A true JPH028251A (en) | 1990-01-11 |
Family
ID=15709703
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP16018788A Pending JPH028251A (en) | 1988-06-28 | 1988-06-28 | Purification of polycyclic quinone pigment by sublimation and photoreceptor for electrophotography containing the same pigment |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH028251A (en) |
Cited By (6)
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JPH04162046A (en) * | 1990-10-26 | 1992-06-05 | Fuji Xerox Co Ltd | Electrophotographic photosensitive body |
US5678229A (en) * | 1994-08-15 | 1997-10-14 | Nec Corporation | Battery-powered accessory for radio data communication of a data processing apparatus |
US5754588A (en) * | 1994-08-15 | 1998-05-19 | Nec Corporation | Radio modem |
EP1403237A1 (en) * | 2001-07-05 | 2004-03-31 | Asahi Glass Company Ltd. | Device and method for refining solid material |
JP2009025346A (en) * | 2007-07-17 | 2009-02-05 | Konica Minolta Business Technologies Inc | Organic photoreceptor and image forming apparatus |
JP2010244562A (en) * | 2010-06-01 | 2010-10-28 | Fujitsu Ltd | System using input-output interface device |
-
1988
- 1988-06-28 JP JP16018788A patent/JPH028251A/en active Pending
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH04162046A (en) * | 1990-10-26 | 1992-06-05 | Fuji Xerox Co Ltd | Electrophotographic photosensitive body |
US5678229A (en) * | 1994-08-15 | 1997-10-14 | Nec Corporation | Battery-powered accessory for radio data communication of a data processing apparatus |
US5754588A (en) * | 1994-08-15 | 1998-05-19 | Nec Corporation | Radio modem |
EP1403237A1 (en) * | 2001-07-05 | 2004-03-31 | Asahi Glass Company Ltd. | Device and method for refining solid material |
EP1403237A4 (en) * | 2001-07-05 | 2004-09-08 | Asahi Glass Co Ltd | Device and method for refining solid material |
JP2009025346A (en) * | 2007-07-17 | 2009-02-05 | Konica Minolta Business Technologies Inc | Organic photoreceptor and image forming apparatus |
JP2010244562A (en) * | 2010-06-01 | 2010-10-28 | Fujitsu Ltd | System using input-output interface device |
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