JPS63198068A - Electrophotographic sensitive body - Google Patents
Electrophotographic sensitive bodyInfo
- Publication number
- JPS63198068A JPS63198068A JP3122887A JP3122887A JPS63198068A JP S63198068 A JPS63198068 A JP S63198068A JP 3122887 A JP3122887 A JP 3122887A JP 3122887 A JP3122887 A JP 3122887A JP S63198068 A JPS63198068 A JP S63198068A
- Authority
- JP
- Japan
- Prior art keywords
- group
- electrophotographic photoreceptor
- atom
- titanium phthalocyanine
- charge transfer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- -1 titanium phthalocyanine compound Chemical class 0.000 claims abstract description 19
- 238000012546 transfer Methods 0.000 claims abstract description 18
- 239000010936 titanium Substances 0.000 claims abstract description 16
- 229910052719 titanium Inorganic materials 0.000 claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 14
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
- 125000005843 halogen group Chemical group 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 125000003277 amino group Chemical group 0.000 claims abstract description 5
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- 125000003118 aryl group Chemical group 0.000 claims abstract description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 3
- 108091008695 photoreceptors Proteins 0.000 claims description 31
- 239000003795 chemical substances by application Substances 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 7
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 claims description 7
- 238000002441 X-ray diffraction Methods 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 238000010586 diagram Methods 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 239000011164 primary particle Substances 0.000 claims 1
- 230000035945 sensitivity Effects 0.000 abstract description 16
- 239000000463 material Substances 0.000 abstract description 9
- 239000000758 substrate Substances 0.000 abstract description 5
- 125000003710 aryl alkyl group Chemical group 0.000 abstract description 2
- 125000004429 atom Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 34
- 229920005989 resin Polymers 0.000 description 22
- 239000011347 resin Substances 0.000 description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 238000000576 coating method Methods 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 238000007740 vapor deposition Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000004677 Nylon Substances 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 229920001778 nylon Polymers 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 239000005020 polyethylene terephthalate Substances 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 229920002433 Vinyl chloride-vinyl acetate copolymer Polymers 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 150000002484 inorganic compounds Chemical class 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- MXGLXCNJJYLFKV-UHFFFAOYSA-N 2-chloroethenoxybenzene Chemical compound ClC=COC1=CC=CC=C1 MXGLXCNJJYLFKV-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- WUPHOULIZUERAE-UHFFFAOYSA-N 3-(oxolan-2-yl)propanoic acid Chemical compound OC(=O)CCC1CCCO1 WUPHOULIZUERAE-UHFFFAOYSA-N 0.000 description 1
- 229920002799 BoPET Polymers 0.000 description 1
- 229910001369 Brass Inorganic materials 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229920008651 Crystalline Polyethylene terephthalate Polymers 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 229910001370 Se alloy Inorganic materials 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- 229910052581 Si3N4 Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000010951 brass Substances 0.000 description 1
- 229910052980 cadmium sulfide Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000002564 cardiac stress test Methods 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920002382 photo conductive polymer Polymers 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920006122 polyamide resin 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
- 229920006254 polymer film Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 239000002356 single layer 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
- 230000003068 static effect Effects 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 238000009423 ventilation Methods 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
- G03G5/0666—Dyes containing a methine or polymethine group
- G03G5/0672—Dyes containing a methine or polymethine group containing two or more methine or polymethine 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
- G03G5/0696—Phthalocyanines
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Photoreceptors In Electrophotography (AREA)
Abstract
Description
【発明の詳細な説明】
〔発明の目的〕
（産業上の利用分野）
本発明は、電子写真感光体に関し、更に詳細に言えば、
優れた露光感光特性、波長特性を有する電子写真感光体
に関する。[Detailed Description of the Invention] [Object of the Invention] (Industrial Application Field) The present invention relates to an electrophotographic photoreceptor, and more specifically,
The present invention relates to an electrophotographic photoreceptor having excellent exposure sensitivity characteristics and wavelength characteristics.
（従来の技術） 従来、電子写真感光体の感光体としては、セレン。(Conventional technology) Conventionally, selenium has been used as the photoreceptor for electrophotographic photoreceptors.
セレン合金、酸化亜鉛、硫化カドミウムおよびテルルな
どの無機光導電体を用いたものが主として使用されて来
た。近年、半導体レーザーの発展は目覚ましく、小型で
安定したレーザー発振器が安価に入手出来るようになり
、電子写真用光源として用いられ始めている。しかし、
これらの装置に短波長光を発振する半導体レーザーを用
いるのは、寿命、出力等を考えれば問題が多い、従って
、従来用いられて来た短波長領域に感度を持つ材料を半
導体レーザー用に使うには不適当であり、長波長領域（
７８０ｎｍ以上）に高感度を持つ材料を研究する必要が
生じて来た。最近は有機系の材料、特に長波長領域に感
度を持つことが期待されるフタロシアニンを使用し、こ
れを積層した積層型有機感光体の研究が盛んに行なわれ
ている。長波長領域に高感度を持つフタロシアニン（Ｐ
ｃ）系材料としては、既に、ε型銅フタロシアニン（ε
−ＣｕＰｃ）、Ｘ型無金属フタロシアニン（Ｘ−Ｒ２Ｐ
ｃ）およびτ型無金属フタロシアニン（τ−Ｈ２Ｐｃ）
が公知であるが、従来の電荷移動剤と組み合わせて形成
された電子写真感光体は。Inorganic photoconductors such as selenium alloys, zinc oxide, cadmium sulfide and tellurium have been used primarily. In recent years, the development of semiconductor lasers has been remarkable, and small and stable laser oscillators have become available at low cost and are beginning to be used as light sources for electrophotography. but,
Using semiconductor lasers that emit short wavelength light in these devices has many problems in terms of lifespan, output, etc. Therefore, materials that are sensitive to the short wavelength region that have been used in the past should be used for semiconductor lasers. It is unsuitable for long wavelength region (
It has become necessary to research materials with high sensitivity to wavelengths of 780 nm and above. Recently, research has been actively conducted on multilayer organic photoreceptors using organic materials, especially phthalocyanine, which is expected to have sensitivity in the long wavelength region. Phthalocyanine (P) has high sensitivity in the long wavelength region.
As a c) type material, ε-type copper phthalocyanine (ε
-CuPc), X-type metal-free phthalocyanine (X-R2P
c) and τ-type metal-free phthalocyanine (τ-H2Pc)
is known, but electrophotographic photoreceptors formed in combination with conventional charge transfer agents.
感度、繰り返し使用時の安定性およびフォトメモリー性
等に問題があり、実際に使用する場合充分とは言えない
レベルであった。There were problems with sensitivity, stability during repeated use, photomemory properties, etc., and the level was not sufficient for actual use.
（発明が解決しようとする問題点）
本発明の目的は、優れた露光感度特性、７８０ｎｍ以上
の長波長領域に高感度、繰り返し使用時に安定で、フォ
トメモリー性の良好である電子写真感光体を得ることに
ある。(Problems to be Solved by the Invention) An object of the present invention is to provide an electrophotographic photoreceptor that has excellent exposure sensitivity characteristics, high sensitivity in the long wavelength region of 780 nm or more, is stable during repeated use, and has good photomemory properties. It's about getting.
（問題点を解決するための手段および作用）上記の目的
は、導電性支持体上に、電荷発生剤として一般式（１）
で示されるチタンフタロシアニン系化合物を使用し、電
荷移動剤として一般式（ｎ）で示される化合物を使用す
ることを特徴とする本発明の電子写真感光体により達成
される。(Means and effects for solving the problem) The above object is to apply a compound of the general formula (1) as a charge generating agent on a conductive support.
This is achieved by the electrophotographic photoreceptor of the present invention, which is characterized in that it uses a titanium phthalocyanine compound represented by the formula (n) and a compound represented by the general formula (n) as a charge transfer agent.
本発明で使用するチタンフタロシアニン系化合物は、モ
ーザーおよびトーマスの「フタロシアニン化合物Ｊ （
Ｍｏ５ｅｒ ａｎｄ Ｔｈｏｎ＋ａｓ ”Ｐｈｔｈａｌ
ｏｃｙａｎｉｎｅ Ｃｏｍｐ。The titanium phthalocyanine compound used in the present invention is ``phthalocyanine compound J'' by Moser and Thomas.
Mo5er and Thon+as ”Phthal
ocyanine Comp.
ｕｎｄｓ’ ）記載の方法、ＵＳＰ３８２５４２２号、
特開昭５９−４９５４４号、特開昭５９−１６６９５９
号、特開昭６１−１０９０５６号、特開昭６１−１７１
７７１号、特開昭６１−２１７０５０号および特開昭６
１−２３９２４８号公報記載の方法やその他の公知方法
により製着されたものでも良い、チタンフタロシアニン
系化合物は、一般式〔Ｉ〕で表されるが、フタロシアニ
ンの中心核にチタニウムが配位したものであれば、いず
れの結晶状態、を換基を有していても良い、また、Ｘ線
回折図は置換基の種類や数により影響を受けず、結晶状
態により差異（式中＋Ｒ１はハロゲン原子、酸素原子、
アルコキシ基を表し、ＲオＩ Ｒｓ ｌ Ｒ４およびＲ
３は、水素原子、ハロゲン原子、アルキル基、アルコキ
シ基。unds'), USP No. 3,825,422,
JP-A-59-49544, JP-A-59-166959
No., JP-A-61-109056, JP-A-61-171
No. 771, JP-A-61-217050 and JP-A-6
The titanium phthalocyanine compound, which may be produced by the method described in Publication No. 1-239248 or other known methods, is represented by the general formula [I], and is a compound in which titanium is coordinated to the central core of phthalocyanine. If so, any crystal state may have a substituent. In addition, the X-ray diffraction pattern is not affected by the type or number of substituents, and differs depending on the crystal state (in the formula, +R1 is a halogen atom). , oxygen atom,
Represents an alkoxy group, R o I Rs l R4 and R
3 is a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group.
了り−ル基、アリールオキシ基、ニトロ基、シアノ基、
水酸基、ベンジルオキシ基、アミノ基等の置換基を表し
、ｊは１または２の整数、 ｋ、 ｌ、 ｍおよ“″
。〜４′）整数を表１・ゝ 〔１コ電荷移動剤
は、一般式（ＩＩ）で示される化合物である。Aryl group, aryloxy group, nitro group, cyano group,
Represents a substituent such as a hydroxyl group, a benzyloxy group, an amino group, j is an integer of 1 or 2, k, l, m and ""
. ~4') Integers are shown in Table 1. [1] The charge transfer agent is a compound represented by the general formula (II).
（式中＋ Ｒｈ＋ Ｒｔｌ ＲｓおよびＲ１は、水素原
子。(In the formula, + Rh + Rtl Rs and R1 are hydrogen atoms.
アルキル基、アラルキル基、アリル基、アルコキシ基、
またはＲ８とＲｔ、ＲｓとＲ９とが結合する窒素原子と
共に環式アミノ基を形成する残基を表す。）感光体は、
導電性基板上に、下引き層、電荷発生層、電荷移動層の
順に積層されたものが、高感度であるため望ましいが、
下引き層、電荷移動層、電荷発生層の順で積層されたも
の、下引き層上に電荷発生剤と電荷移動剤とを適当な樹
脂で分散して単層塗布されたものでも良い。Alkyl group, aralkyl group, allyl group, alkoxy group,
Alternatively, it represents a residue that forms a cyclic amino group together with the nitrogen atom to which R8 and Rt or Rs and R9 are bonded. ) The photoreceptor is
A structure in which an undercoat layer, a charge generation layer, and a charge transfer layer are laminated in this order on a conductive substrate is desirable because of its high sensitivity.
It may be one in which an undercoat layer, a charge transfer layer, and a charge generation layer are laminated in this order, or one in which a charge generation agent and a charge transfer agent are dispersed in a suitable resin and coated in a single layer on the undercoat layer.
また、必要に応じて下引き層を除いたもの、樹脂または
無機化合物で最上層にオーバーコート層を設けたもので
も良い。Alternatively, the undercoat layer may be removed or an overcoat layer made of a resin or an inorganic compound may be provided as the uppermost layer, if necessary.
電荷発生層は、蒸着法または分散塗工法により形成され
る。The charge generation layer is formed by a vapor deposition method or a dispersion coating method.
蒸着は、４００℃〜６００℃の温度範囲で１０−ｓ〜１
０−”Ｔｏｒｒの真空下で行われる。分散塗工は、樹脂
なしで、あるいは接着性向上などの目的で、適当な樹脂
溶液中にチタンフタロシアニン系化合物を分散した塗液
を使用して行われる。塗工は、スピンコーター、アプリ
ケーター、浸漬コーターおよびスプレーコーター等の装
置を用いて行い、乾燥は、望ましくは加熱乾燥で４０〜
２００℃、１０分〜６時間の範囲で静止または送風条件
下で行なう。乾燥後膜厚は０．０１から５ミクロン、望
ましくは０．１から１ミクロンになるように塗工される
。Vapor deposition was performed for 10-s to 1 at a temperature range of 400°C to 600°C.
It is carried out under a vacuum of 0-'' Torr. Dispersion coating is carried out without a resin or by using a coating liquid in which a titanium phthalocyanine compound is dispersed in a suitable resin solution for the purpose of improving adhesion. Coating is performed using equipment such as a spin coater, applicator, dip coater, and spray coater, and drying is preferably performed by heating for 40 to 40 minutes.
The test is carried out at 200° C. for 10 minutes to 6 hours under stationary or ventilation conditions. After drying, the film is coated to a thickness of 0.01 to 5 microns, preferably 0.1 to 1 micron.
電荷発生層を塗工によって形成する際に用いうるバイン
ダーとしては広範な絶縁性樹脂から選択でき。The binder that can be used when forming the charge generation layer by coating can be selected from a wide variety of insulating resins.
ポリ−Ｎ−ビニルカルバゾール、ポリビニルアントラセ
ンやポリビニルピレンなどの有機光導電性ポリマーも使
用出来る。好ましくは、ポリビニルブチラール、ポリエ
ステル、ポリカーボネート、ポリメチルメタクリレート
、アクリル、シリコン、ウレタン、エポキシ、フェノキ
シ、塩化ビニル、塩化ビニル−酢酸ビニル共重合体等の
樹脂が使用されるが。Organic photoconductive polymers such as poly-N-vinylcarbazole, polyvinylanthracene and polyvinylpyrene can also be used. Preferably, resins such as polyvinyl butyral, polyester, polycarbonate, polymethyl methacrylate, acrylic, silicone, urethane, epoxy, phenoxy, vinyl chloride, and vinyl chloride-vinyl acetate copolymer are used.
絶縁性樹脂であれば、いずれのものでも良い。電荷発生
層中に含有する樹脂は、電荷発生剤に対して。Any insulating resin may be used. The resin contained in the charge generation layer is different from the charge generation agent.
１００重量％以下、好ましくは４０重量％以下が適して
いる。また、これらの樹脂は、１種または２種以上組み
合わせても良く、必要に応じて、熱硬化性樹脂を架橋す
る目的でイソシアネート、メラミン樹脂などの架橋用樹
脂を添加して使用することも可能である。A content of 100% by weight or less, preferably 40% by weight or less is suitable. In addition, these resins may be used alone or in combination of two or more, and if necessary, it is also possible to add a crosslinking resin such as isocyanate or melamine resin for the purpose of crosslinking the thermosetting resin. It is.
使用する溶剤は、樹脂の種類により異なり、後述する電
荷移動層や下引き層に、悪影響を及ぼさないものが選択
される。具体的にはベンゼン、キシレン。The solvent to be used varies depending on the type of resin, and a solvent is selected that does not adversely affect the charge transfer layer and undercoat layer, which will be described later. Specifically benzene and xylene.
リグロイン、モノクロルベンゼン、ジクロルベンゼンな
どの芳香族炭化水素、アセトン、メチルエチルケトン、
シクロヘキサノンなどのケトン類、メタノール、エタノ
ール、イソプロパツールなどのアルコール類、酢酸エチ
ル、メチルセロソルブ、などのエステル類、四塩化炭素
、クロロホルム、ジクロルメタン、ジクロルエタン、ト
リクロルエチレンなどの脂肪族ハロゲン化炭化水素類、
テトラヒドロフラン、ジオキサン、エチレングリコール
モノメチルエーテルなどのエーテル類、Ｎ、Ｎ−ジメチ
ルホルムアミド、Ｎ、Ｎ−ジメチルアセトアミドなどの
アミド類、およびジメチルスルホキシドなどのスルホキ
シド類が用いられる。Aromatic hydrocarbons such as ligroin, monochlorobenzene, dichlorobenzene, acetone, methyl ethyl ketone,
Ketones such as cyclohexanone, alcohols such as methanol, ethanol, and isopropanol, esters such as ethyl acetate and methyl cellosolve, and aliphatic halogenated hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, dichloroethane, and trichlorethylene. ,
Ethers such as tetrahydrofuran, dioxane and ethylene glycol monomethyl ether, amides such as N,N-dimethylformamide and N,N-dimethylacetamide, and sulfoxides such as dimethylsulfoxide are used.
電荷移動層は、電荷移動剤を単体または結着剤樹脂と共
に適切な溶剤に溶解分散して塗工形成される。The charge transfer layer is formed by coating and dispersing a charge transfer agent alone or together with a binder resin in an appropriate solvent.
電荷移動剤は、一般式（ｎ）で示される化合物を使用す
る。電荷移動層に用いられる樹脂は、電荷発生層で使用
される樹脂として挙げたものの中から選択される。塗工
は、スピンコーター、アプリケーター。As the charge transfer agent, a compound represented by general formula (n) is used. The resin used in the charge transport layer is selected from those listed as resins used in the charge generation layer. Coating is done using a spin coater or applicator.
浸漬コーターおよびスプレーコーター等の装置を用いて
行い、乾燥後の膜厚は、５から５０μｍ、望ましくは、
１０〜２０μｍが良い。It is carried out using a device such as a dip coater or a spray coater, and the film thickness after drying is 5 to 50 μm, preferably,
The thickness is preferably 10 to 20 μm.
樹脂と一般式（ＩＩ）の化合物との配合割合は、樹脂１
００重量部当たり、一般式（ＩＩ）の化合物を１０〜５
００重量部とすることが好ましい。また、これらの樹脂
は、１種または２種以上組み合わせて用いても良い。The blending ratio of the resin and the compound of general formula (II) is as follows: resin 1
10 to 5 parts of the compound of general formula (II) per 00 parts by weight
It is preferable to set it as 00 parts by weight. Further, these resins may be used alone or in combination of two or more.
また１本発明の電荷移動層を形成させる際に使用する溶
剤は多数の有用な有機溶剤を包含している。Furthermore, the solvent used in forming the charge transport layer of the present invention includes many useful organic solvents.
例えば、ベンゼン、トルエン、キシレン、クロルベンゼ
ン、ナフタリンなどの芳香族炭化水素類、アセトン２−
ブタノンなどのケトン類、塩化メチレン。For example, aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene, naphthalene, acetone 2-
Ketones such as butanone, methylene chloride.
塩化エチレン、クロロホルムなどのハロゲン化脂肪族炭
化水素類、テトラヒドロフラン、１．４−ジオキサン、
エチルエーテルなどの環状、もしくは直鎖状のエーテル
類など、あるいはこれらの混合溶剤を挙げることが出来
る。Halogenated aliphatic hydrocarbons such as ethylene chloride and chloroform, tetrahydrofuran, 1,4-dioxane,
Examples include cyclic or linear ethers such as ethyl ether, and mixed solvents thereof.
これらの各層に加えて、帯電安定性や接着性向上の目的
で、下引き層を導電性基板上に設けることが出来る。下
引き層としては、ナイロン、共重合ナイロン、アルコキ
シメチル化ナイロンなどのポリアミド樹脂、カゼイン、
ポリビニルアルコール、ゼラチン、ポリビニルブチラー
ル等の樹脂、酸化アルミニウムなどの無機化合物、およ
び導電性基板自身を酸化処理などにより絶縁性付与した
ものがある。また。In addition to these layers, an undercoat layer can be provided on the conductive substrate for the purpose of improving charging stability and adhesion. For the undercoat layer, polyamide resins such as nylon, copolymerized nylon, alkoxymethylated nylon, casein,
There are resins such as polyvinyl alcohol, gelatin, and polyvinyl butyral, inorganic compounds such as aluminum oxide, and conductive substrates that have been given insulation properties by oxidation treatment or the like. Also.
酸化亜鉛や酸化チタンなどの金属酸化物やカーボンブラ
ンク、炭化ケイ素および窒化ケイ素などの導電性および
誘電性粒子を樹脂中に含有させて下引き層の導電性を調
整することも出来る。膜厚は０．０１から５０μｍ、望
ましくは０．１から１μｍが良い。The conductivity of the undercoat layer can also be adjusted by incorporating conductive and dielectric particles such as metal oxides such as zinc oxide and titanium oxide, carbon blanks, silicon carbide and silicon nitride into the resin. The film thickness is preferably 0.01 to 50 μm, preferably 0.1 to 1 μm.
本発明の電子写真感光体に用いる支持体としては。The support used in the electrophotographic photoreceptor of the present invention includes:
導電性が付与されていれば何れのものでも良く、従来使
われている何れのタイプの導電層であってもさしつかえ
ない。具体的には、アルミニウム、銅、ステンレス、鉄
、真ちゅう、スズおよびニッケルなどの金属や、それら
金属を用いて紙、プラスチック。Any material may be used as long as it is imparted with electrical conductivity, and any type of electrically conductive layer conventionally used may be used. Specifically, metals such as aluminum, copper, stainless steel, iron, brass, tin, and nickel, as well as paper and plastics using these metals.
ポリエチレンテレフタレートＣＰＥＴ）などの高分子フ
ィルム上に蒸着またはラミネート等の処理を行い、導電
性を持たせた物であっても良い。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。The material may be made conductive by performing a process such as vapor deposition or lamination on a polymer film such as polyethylene terephthalate (CPET). Also, its shape can be sheet-like or cylinder-like.
その他のものであっても差しつかえない。Other items are also acceptable.
プリンター用のデジタル光源として、ＬＥＤも実用化さ
れている。LEDs have also been put into practical use as digital light sources for printers.
可視光領域のＬＥＤも使われているが、一般に実用化さ
れているものは、６５０部ｍ以上、標準的には６６０部
ｍの発振波長を持っている。当該電子写真感光体は、６
５０部ｍ前後に分光悪魔ビークを持つため、ＬＥＤ用材
料としても有効である。LEDs in the visible light range are also used, but those that are generally put into practical use have an oscillation wavelength of 650 parts m or more, typically 660 parts m. The electrophotographic photoreceptor is 6
Since it has a spectral devil's peak around 50 parts m, it is also effective as a material for LEDs.
以下９本発明の実施例について具体的に説明する。Hereinafter, nine embodiments of the present invention will be specifically described.
例中で部とは重量部を示す。In the examples, parts refer to parts by weight.
実施例１〜２１
共重合ナイロン（東し製アミランＣＭ−８０００）１０
部をエタノール１９０部とともにボールミルで３時間混
合し、溶解させた塗液を、ポリエチレンテレフタレート
（ＰＥＴ）フィルム上にアルミニウムを蒸着したシート
上に、ワイヤーバーで塗布した後、１００℃で１時間乾
燥させて膜厚０．５ミクロンの下引き層を持つシートを
得た。Examples 1 to 21 Copolymerized nylon (Amiran CM-8000 manufactured by Toshi) 10
was mixed with 190 parts of ethanol in a ball mill for 3 hours, and the dissolved coating liquid was applied with a wire bar onto a sheet of polyethylene terephthalate (PET) film with aluminum vapor-deposited, and then dried at 100°C for 1 hour. A sheet having a subbing layer with a thickness of 0.5 microns was obtained.
次に、第１表に示すチタンフタロシアニン系化合物の例
示化合物を電荷発生剤として使用した。Next, exemplified titanium phthalocyanine compounds shown in Table 1 were used as charge generating agents.
第１表
表２表
第１表に示す、チタンフタロシアニン系化合物のＸ線回
折図（ａ）〜（ｇ）は、第１図に載げたものであり、結
晶パターンは化学式によるものではない。The X-ray diffraction patterns (a) to (g) of titanium phthalocyanine compounds shown in Table 1 and Table 2 are shown in FIG. 1, and the crystal patterns are not based on chemical formulas.
本実施例１〜２１のチタンフタロシアニン系化合物２部
をジオキサン９７部に塩ビー酢ビ共重合樹脂１部（ユニ
オンカーバイド社製ＶＭＣＨ）を溶解した樹脂液ととも
にボールミルで２時間分散した。Two parts of the titanium phthalocyanine compounds of Examples 1 to 21 were dispersed in a ball mill for 2 hours together with a resin solution prepared by dissolving 1 part of vinyl chloride-vinyl acetate copolymer resin (VMCH manufactured by Union Carbide) in 97 parts of dioxane.
この分散液を下引き層上に塗布し、１００℃で１時間乾
燥した後、０．２μｍの電荷発生層を形成する。This dispersion is applied onto the undercoat layer and dried at 100° C. for 1 hour to form a charge generation layer of 0.2 μm.
次に電荷移動剤として、一般式（ｎ）の化合物の例示化
合物（Ｉｆ−ａ） １部、ポリカーボネート樹脂（奇
人化成■製パンライ）Ｌ−１２５０）１部を塩化メチレ
ン８部で混合溶解した。この液を電荷発生層上に塗布し
、５０℃で１時間乾燥した後、１５μの電荷移動層を形
成して電子写真感光体を得た。Next, as a charge transfer agent, 1 part of exemplified compound (If-a) of the compound of general formula (n) and 1 part of polycarbonate resin (Panrai L-1250, manufactured by Kijin Kasei Corporation) were mixed and dissolved in 8 parts of methylene chloride. This liquid was applied onto the charge generation layer and dried at 50° C. for 1 hour, after which a 15 μm charge transfer layer was formed to obtain an electrophotographic photoreceptor.
（ｘ−北） 感光体の電子写真特性は、下記の方法で測定した。(x-north) The electrophotographic properties of the photoreceptor were measured by the following method.
静電複写紙試験装置５Ｐ−４２８（川口電機層）により
、スタティックモード２．コロナ帯電は−５゜２ＫＶで
２表面電位および５１ｕｘの白色光を照射して、帯電量
が１／２および１１５まで減少する時間から白色光半減
露光量悪魔（Ｅｌ／２およびＥ１１５）を調べた。また
、繰り返し特性の評価は、−５゜２ＫＶ、コロナ線速度
１２０ ｗ／ｓｅｃの条件で帯電。Static mode 2. For corona charging, 2 surface potential at -5°2KV and white light of 51ux were irradiated, and the white light half-reduction exposure amount (El/2 and E115) was investigated from the time when the charge amount decreased to 1/2 and 115. . In addition, the repetition characteristics were evaluated under the conditions of -5°2 KV and a corona linear velocity of 120 w/sec.
２秒間暗所に放置、５１ｕｘで３秒間露光の順で繰り返
し、初期表面電位（Ｖ６）、２秒間暗所に放置後の電位
（ｖｚ）、 ５１ｕｘで３秒間露光後の残留電位（Ｖ
Ｆ６）、感度（Ｅｌ／２．Ｅ１１５）の変化を測定した
。The initial surface potential (V6), the potential after being left in the dark for 2 seconds (vz), and the residual potential (V) after being exposed for 3 seconds at 51ux are the initial surface potential (V6).
F6), and changes in sensitivity (El/2.E115) were measured.
フォトメモリー性（ＰＭ）は１本怒光体を６００１ｕｘ
の白色光下で３分間放置した後に、暗所に１分間放置し
て、再び同一条件で静電特性を測定する。Photo memory (PM) is 6001ux for one angry light body.
After being left under white light for 3 minutes, it was left in a dark place for 1 minute, and the electrostatic properties were measured again under the same conditions.
そこで、６００１ｕｘ照射前の感光体の帯電電位と照射
後の帯電電位の変化を、フォトメモリー（ＰＭ）とした
、従って、フォトメモリー（ＰＭ）は次式で示される。Therefore, the change in the charged potential of the photoreceptor before 6001 ux irradiation and the charged potential after irradiation was defined as photomemory (PM). Therefore, photomemory (PM) is expressed by the following equation.
ＰＭ−強照度（６００１ｕｘ ）露光前の表面電位−強
照度露光後の表面電位
第２表
第２表＜ＨＡき）
第２表（続き）
第２表に示した結果より９本実施例により得られた電子
写真感光体は、感度が優れ、残留電位も少なく、１００
００回の繰り返し試験後も、初期の特性とほとんど変わ
らない極めて良好な結果が得られた。また、フォトメモ
リー（ＰＭ）も小さく、照射光に対して安定な感光体で
あることがわかる。PM - Surface potential before exposure to strong illuminance (6001ux) - Surface potential after exposure to strong illuminance The electrophotographic photoreceptor has excellent sensitivity, low residual potential, and 100
Even after repeated testing 00 times, very good results were obtained with almost no change in the initial characteristics. Furthermore, the photomemory (PM) is small, and it is understood that the photoreceptor is stable against irradiation light.
実施例２２〜２８
第３表に示したチタンフタロシアニン系化合物の例示化
合物を使い蒸着法で電荷発生層を形成した。チタンフタ
ロシアニン系化合物１０部を１０−’Ｔｏｒｒの真空条
件下で４５０℃に加熱昇華させ、冷却した基板上に析出
させて９．５部の結晶を得た。実施例１〜２１と同条件
で形成した下引き層を有するＰＥＴフィルム上に、１０
”’Ｔｏｒｒの真空条件下、５５０℃で０．１５μｍの
膜厚の電荷発生層を得た。その上に、実施例１〜２１と
同条件で電荷移動層を作成し、電子写真特性を測定した
。Examples 22 to 28 Charge generation layers were formed by vapor deposition using the titanium phthalocyanine compounds listed in Table 3. 10 parts of a titanium phthalocyanine compound was heated and sublimated at 450° C. under a vacuum condition of 10-' Torr, and deposited on a cooled substrate to obtain 9.5 parts of crystals. On a PET film having an undercoat layer formed under the same conditions as Examples 1 to 21, 10
A charge generation layer with a film thickness of 0.15 μm was obtained at 550° C. under a vacuum condition of “’ Torr.A charge transfer layer was formed thereon under the same conditions as in Examples 1 to 21, and the electrophotographic properties were measured. did.
第３表
第４表
第４表の結果より、蒸着法で得られた電荷発生層を有す
る電子写真感光体においても、一般式（Ｉｆ）で示され
る電荷移動剤と組み合わせることにより、極めて良好な
結果が得られた。また、フォトメモリー（ＰＭ）も小さ
く、照射光に対して安定な感光体であることがわかる。From the results shown in Table 3 and Table 4, even in electrophotographic photoreceptors having charge generation layers obtained by vapor deposition, by combining with the charge transfer agent represented by the general formula (If), extremely good results can be obtained. The results were obtained. Furthermore, the photomemory (PM) is small, and it is understood that the photoreceptor is stable against irradiation light.
比較例１〜４
実施例１〜２８で用いた２例示化合物（Ｉｆ−ａ）に代
えて、第５表に示す電荷移動剤を使用し、第５表に示す
条件の他は、実施例１〜２８と同条件で感光体を作成し
。Comparative Examples 1 to 4 In place of the two exemplified compounds (If-a) used in Examples 1 to 28, charge transfer agents shown in Table 5 were used, and except for the conditions shown in Table 5, Example 1 A photoreceptor was prepared under the same conditions as in ~28.
電子写真特性を比較した。結果を第６表に示す。The electrophotographic properties were compared. The results are shown in Table 6.
第５表
第６表
比較例１〜４の結果を実施例と比較すると、残留電位が
高（、感度も劣り、繰り返しでの安定性も不足している
。また、フォトメモリーも大きく光照射により表面電位
が大きく低下している。Comparing the results of Comparative Examples 1 to 4 in Table 5 and Table 6 with the Examples, it is found that the residual potential is high (the sensitivity is poor, and the stability with repeated use is insufficient. Also, the photomemory is large and is affected by light irradiation. The surface potential has decreased significantly.
フォトメモリーとは、電子写真感光体に強い光を照射し
た場合、その後の帯電、露光プロセスで生ずる怒光体表
面の保持電位が、光照射以前に比べて大きく変動してし
まう現象である。その光の強度によっては、一時的な場
合もあり、永久に回復しない場合もある。従って、フォ
トメモリー性が小さいと感光体の取り扱い時に、照射光
や自然光にさらしても帯電性が安定しているために、実
際に複写機およびプリンター等で使用する場合、掻めて
安定した電子写真特性が得られる。それにより画像的に
も安定した良質の画像が得られる利点がある。Photomemory is a phenomenon in which when an electrophotographic photoreceptor is irradiated with strong light, the potential held on the surface of the photoreceptor during the subsequent charging and exposure processes fluctuates significantly compared to before the light irradiation. Depending on the intensity of the light, it may be temporary or may not recover permanently. Therefore, when handling the photoreceptor, if the photomemory property is small, the charging property will be stable even when exposed to irradiation light or natural light, so when actually used in copiers and printers, it is necessary to Photographic properties are obtained. This has the advantage that a stable and high quality image can be obtained.
本発明の電子写真感光体は、高感度、繰り返し使用時に
安定であり、フォトメモリー性が良好であるばかりでな
く、安定した良質の画像を得ることが出来た。The electrophotographic photoreceptor of the present invention not only has high sensitivity, is stable upon repeated use, and has good photomemory properties, but also can produce stable and high-quality images.
（発明の効果）
本発明により高感度および繰り返し使用時に安定であり
、フォトメモリー性の良好な、安定した良質の画像を提
供する電子写真感光体が得られた。(Effects of the Invention) According to the present invention, an electrophotographic photoreceptor that has high sensitivity, is stable during repeated use, has good photomemory properties, and provides stable, high-quality images was obtained.
第１図は、実施例１〜２８および比較例１〜４で使用し
たチタンフタロシアニン系化合物のＸ線回折図である。FIG. 1 is an X-ray diffraction diagram of the titanium phthalocyanine compounds used in Examples 1 to 28 and Comparative Examples 1 to 4.
Claims (1)
使用してなる電子写真感光体において、電荷発生剤が一
般式〔 I 〕で示されるチタンフタロシアニン系化合物
であり電荷移動剤が一般式〔II〕で示される化合物であ
ることを特徴とする電子写真感光体。 ▲数式、化学式、表等があります▼〔 I 〕 （式中、Ｒ＿１はハロゲン原子、酸素原子、アルコキシ
基を表し、Ｒ＿２、Ｒ＿３、Ｒ＿４およびＲ＿５は、水
素原子、ハロゲン原子、アルキル基、アルコキシ基、ア
リール基、アリールオキシ基、ニトロ基、シアノ基、水
酸基、ベンジルオキシ基、アミノ基等の置換基を表し、
ｊは１または２の整数、ｋ、ｌ、ｍおよびｎは０〜４の
整数を表す。） ［II］▲数式、化学式、表等があります▼ （式中、Ｒ＿６、Ｒ＿７、Ｒ＿８およびＲ＿９は、水素
原子、アルキル基、アラルキル基、アリル基、アルコキ
シ基、またはＲ＿６、Ｒ＿７、Ｒ＿８とＲ＿９とが結合
する窒素原子と共に環式アミノ基を形成する残基を表す
。） ２、Ｘ線回折図において強いピークを示さない非結晶性
であり、一次粒子径が０．２μｍ以下であるチタンフタ
ロシアニン系化合物を用いてなることを特徴とする特許
請求の範囲第１項記載の電子写真感光体。） ３、Ｘ線回折図においてブラッグ角度（２θ±０．２°
）の下記（ａ）、（ｂ）、（ｃ）、（ｄ）もしくは（ｅ
）に示す位置に強いピークを示す、チタンフタロシアニ
ン系化合物の少なくとも１種を用いてなることを特徴と
する特許請求の範囲第１項記載の電子写真感光体。 （ａ）７．５°、２２．４°、２４．４°、２５．４°
、２６．２°、２７．２°および２８．６° （ｂ）７．５°、２２．４°、２４．４°、２５．４°
、２７．２°および２８．６° （ｃ）７．５°、２２．４°、２４．４°、２５．４°
、２６．２°および２８．６° （ｄ）７．５°、２２．４°、２４．４°、２５．４°
および２８．６° （ｅ）６．９°、１５．５°および２３．４° （ｆ）１３．１°、２０．６°、２６．２°、２６．５
°および２７．０° ４、導電性支持体上に無機物または有機物の下引き層を
有する特許請求の範囲第１〜３項記載の電子写真感光体
。[Claims] 1. An electrophotographic photoreceptor comprising a charge generating agent and a charge transfer agent on a conductive support, wherein the charge generating agent is a titanium phthalocyanine compound represented by the general formula [I]. An electrophotographic photoreceptor, wherein the charge transfer agent is a compound represented by the general formula [II]. ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [I] (In the formula, R_1 represents a halogen atom, an oxygen atom, or an alkoxy group, and R_2, R_3, R_4, and R_5 represent a hydrogen atom, a halogen atom, an alkyl group, or an alkoxy group. , represents a substituent such as an aryl group, an aryloxy group, a nitro group, a cyano group, a hydroxyl group, a benzyloxy group, an amino group,
j is an integer of 1 or 2, and k, l, m and n are integers of 0 to 4. ) [II] ▲ Numerical formulas, chemical formulas, tables, etc. represents a residue that forms a cyclic amino group with the nitrogen atom to which it is bonded.) 2. Titanium phthalocyanine that is non-crystalline and does not show strong peaks in an X-ray diffraction diagram, and has a primary particle size of 0.2 μm or less. 2. The electrophotographic photoreceptor according to claim 1, characterized in that the electrophotographic photoreceptor is formed using a compound based on the electrophotographic method. ) 3. Bragg angle (2θ±0.2°
) below (a), (b), (c), (d) or (e
2. The electrophotographic photoreceptor according to claim 1, wherein the electrophotographic photoreceptor is made of at least one titanium phthalocyanine compound that exhibits a strong peak at the position shown in (a). (a) 7.5°, 22.4°, 24.4°, 25.4°
, 26.2°, 27.2° and 28.6° (b) 7.5°, 22.4°, 24.4°, 25.4°
, 27.2° and 28.6° (c) 7.5°, 22.4°, 24.4°, 25.4°
, 26.2° and 28.6° (d) 7.5°, 22.4°, 24.4°, 25.4°
and 28.6° (e) 6.9°, 15.5° and 23.4° (f) 13.1°, 20.6°, 26.2°, 26.5
4. The electrophotographic photoreceptor according to claims 1 to 3, which has an inorganic or organic subbing layer on a conductive support.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3122887A JPS63198068A (en) | 1987-02-13 | 1987-02-13 | Electrophotographic sensitive body |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3122887A JPS63198068A (en) | 1987-02-13 | 1987-02-13 | Electrophotographic sensitive body |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS63198068A true JPS63198068A (en) | 1988-08-16 |
Family
ID=12325557
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3122887A Pending JPS63198068A (en) | 1987-02-13 | 1987-02-13 | Electrophotographic sensitive body |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63198068A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01131544A (en) * | 1987-08-21 | 1989-05-24 | Konica Corp | Production of negative silver halide photographic emulsion |
| JPH01261652A (en) * | 1988-04-12 | 1989-10-18 | Konica Corp | Electrophotographic sensitive body |
| US5079119A (en) * | 1989-02-23 | 1992-01-07 | Konica Corporation | Photoreceptor |
| JP2008174753A (en) * | 2008-02-14 | 2008-07-31 | Mitsubishi Chemicals Corp | Titanylphthalocyanine compound and electrophotographic photoreceptor using the same |
-
1987
- 1987-02-13 JP JP3122887A patent/JPS63198068A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01131544A (en) * | 1987-08-21 | 1989-05-24 | Konica Corp | Production of negative silver halide photographic emulsion |
| JPH01261652A (en) * | 1988-04-12 | 1989-10-18 | Konica Corp | Electrophotographic sensitive body |
| US5079119A (en) * | 1989-02-23 | 1992-01-07 | Konica Corporation | Photoreceptor |
| JP2008174753A (en) * | 2008-02-14 | 2008-07-31 | Mitsubishi Chemicals Corp | Titanylphthalocyanine compound and electrophotographic photoreceptor using the same |
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