JPH01298364A - Electrophotographic sensitive body - Google Patents
Electrophotographic sensitive bodyInfo
- Publication number
- JPH01298364A JPH01298364A JP12930588A JP12930588A JPH01298364A JP H01298364 A JPH01298364 A JP H01298364A JP 12930588 A JP12930588 A JP 12930588A JP 12930588 A JP12930588 A JP 12930588A JP H01298364 A JPH01298364 A JP H01298364A
- Authority
- JP
- Japan
- Prior art keywords
- optionally substituted
- group
- trihydrazone
- charge
- 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
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
- 108091008695 photoreceptors Proteins 0.000 claims description 40
- 150000001875 compounds Chemical class 0.000 claims description 25
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 10
- 125000003107 substituted aryl group Chemical group 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 2
- 230000035945 sensitivity Effects 0.000 abstract description 14
- 125000003118 aryl group Chemical group 0.000 abstract description 4
- 238000012546 transfer Methods 0.000 abstract description 4
- 230000006866 deterioration Effects 0.000 abstract description 2
- 239000010410 layer Substances 0.000 description 42
- 239000000463 material Substances 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 239000000049 pigment Substances 0.000 description 10
- 239000011230 binding agent Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- -1 1973-5 466) Chemical class 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000010409 thin film Substances 0.000 description 6
- 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 description 5
- 239000002904 solvent Substances 0.000 description 5
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 229910010272 inorganic material Inorganic materials 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-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
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 229910052711 selenium Inorganic materials 0.000 description 3
- 239000011669 selenium Substances 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- WUPHOULIZUERAE-UHFFFAOYSA-N 3-(oxolan-2-yl)propanoic acid Chemical compound OC(=O)CCC1CCCO1 WUPHOULIZUERAE-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000007983 Tris buffer Substances 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
- 229910021417 amorphous silicon Inorganic materials 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052980 cadmium sulfide Inorganic materials 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 150000002484 inorganic compounds Chemical class 0.000 description 2
- 239000011147 inorganic material Substances 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 230000010355 oscillation Effects 0.000 description 2
- YRZZLAGRKZIJJI-UHFFFAOYSA-N oxyvanadium phthalocyanine Chemical compound [V+2]=O.C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 YRZZLAGRKZIJJI-UHFFFAOYSA-N 0.000 description 2
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920006254 polymer film Polymers 0.000 description 2
- 230000002250 progressing effect Effects 0.000 description 2
- 239000011241 protective layer Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical class C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- ZCKJLLYUQLLGPP-UHFFFAOYSA-N 1-[2-(n-phenylanilino)phenyl]ethanone Chemical compound CC(=O)C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ZCKJLLYUQLLGPP-UHFFFAOYSA-N 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 229920004313 LEXAN™ RESIN 141 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
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- 239000004695 Polyether sulfone Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 229910001370 Se alloy Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- GYMBTLRVABDEHT-UHFFFAOYSA-N chlorobenzene;dichloromethane Chemical compound ClCCl.ClC1=CC=CC=C1 GYMBTLRVABDEHT-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 229920006351 engineering plastic Polymers 0.000 description 1
- 239000003759 ester based solvent Substances 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 125000005597 hydrazone group Chemical group 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000005268 plasma chemical vapour deposition Methods 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- 150000005839 radical cations Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000003068 static effect Effects 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
- 229920001909 styrene-acrylic polymer Polymers 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 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
- 150000004961 triphenylmethanes Chemical class 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000008096 xylene Substances 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
- G03G5/0601—Acyclic or carbocyclic compounds
- G03G5/0612—Acyclic or carbocyclic compounds containing nitrogen
- G03G5/0616—Hydrazines; Hydrazones
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は電子写真感光体に関し、更に詳しくは特定のト
リヒドラゾン化合物を電荷輸送層中に含む、高感度、高
耐久性の電子写真感光体に関する。Detailed Description of the Invention [Field of Industrial Application] The present invention relates to an electrophotographic photoreceptor, and more particularly to a highly sensitive and highly durable electrophotographic photoreceptor containing a specific trihydrazone compound in its charge transport layer. Regarding.
〔従来の技術及び発明が解決しようとする課題〕近年、
電子写真方式を用いた複写機、プリンターの発展は目覚
ましく、用途に応じて様々な形態、種類の機種が開発さ
れ、それに対応してそれらに用いられる感光体も無機材
料から有機材料まで多種多様のものが開発されつつある
。[Problems to be solved by conventional techniques and inventions] In recent years,
The development of copiers and printers using electrophotography has been remarkable, with various forms and types of models being developed depending on the purpose, and correspondingly, the photoreceptors used in these machines are also made of a wide variety of materials, from inorganic to organic materials. Things are being developed.
従来、電子写真感光体としては、その感度、耐久性の面
から無機化合物が主として用いられてきた。これらの無
機化合物としては、例えば酸化亜鉛、硫化カドミウム、
セレン等を挙げることができる。しかしながら、これら
は有害物質を使用している場合が多く、その廃棄が問題
となり、公害をもたらす原因となる。また、感度の良好
なセレンを用いる場合、蒸着法等により導電性基体上に
薄膜を形成する必要があり、生産性が劣り、コストアッ
プの原因となる。近年、無公害性の無機物感光体として
アモルファスシリコンが注目され、その研究開発が進め
られている。しかしながら、これらも、感度については
優れているが、薄膜形成時において、主にプラズマＣＶ
Ｄ法を用いるため、その生産性は極めて劣っており、感
光体コスト、ランニングコストとも大きなものとなって
いる。Conventionally, inorganic compounds have been mainly used as electrophotographic photoreceptors due to their sensitivity and durability. Examples of these inorganic compounds include zinc oxide, cadmium sulfide,
Examples include selenium. However, these often use harmful substances, and their disposal becomes a problem and causes pollution. Furthermore, when selenium, which has good sensitivity, is used, it is necessary to form a thin film on a conductive substrate by a vapor deposition method or the like, resulting in poor productivity and increased costs. In recent years, amorphous silicon has attracted attention as a non-polluting inorganic photoreceptor, and its research and development is progressing. However, although these also have excellent sensitivity, they are mainly used for plasma CV when forming thin films.
Since method D is used, its productivity is extremely poor, and both the photoreceptor cost and running cost are high.
一方、有機感光体は、焼却が可能であり、無公害の利点
を有し、更に多くのものは塗工により薄膜形成が可能で
大量生産が容易である。それ故にコストが大幅に低下で
き、又、用途に応じて様々な形状に加工することができ
るという長所を有している。しかしながら、有機感光体
においては、その感度、耐久性に問題が残されており、
高感度、高耐久性の有機感光体の出現が強く望まれてい
る。On the other hand, organic photoreceptors can be incinerated and have the advantage of being non-polluting, and many of them can be coated to form thin films, making mass production easy. Therefore, it has the advantage of being able to significantly reduce costs and being able to be processed into various shapes depending on the application. However, organic photoreceptors still have problems with their sensitivity and durability.
The emergence of organic photoreceptors with high sensitivity and high durability is strongly desired.
有機感光体の感度向上の手段として様々な方法が提案さ
れているが、現在では電荷発生層と電荷輸送層とに機能
を分離した主に二層構造の機能分離型感光体が主流とな
っている。例えば、露光により電荷発生層で発生した電
荷は、電荷輸送層に注入され、電荷輸送層中を通って表
面に輸送され、表面電荷を中和することにより感光体表
面に静電潜像が形成される。機能分離型は単層型に比し
て発生した電荷が捕獲される可能性が小さくなり、各層
がそれぞれの機能を阻害されることなく、効率良く電荷
が感光体表面に輸送され得る（アメリカ特許第２８０３
５４１号）。Various methods have been proposed to improve the sensitivity of organic photoreceptors, but currently the mainstream is a functionally separated photoreceptor with a two-layer structure in which the functions are separated into a charge generation layer and a charge transport layer. There is. For example, charges generated in the charge generation layer due to exposure to light are injected into the charge transport layer, transported through the charge transport layer to the surface, and by neutralizing the surface charges, an electrostatic latent image is formed on the surface of the photoreceptor. be done. Compared to the single-layer type, the function-separated type has a smaller possibility that generated charges will be captured, and the charges can be efficiently transported to the photoreceptor surface without each layer having its own function inhibited (U.S. patent No. 2803
No. 541).
電荷発生層に用いられる有機電荷発生材としては、照射
される光のエネルギーを吸収し、効率よく電荷を発生す
る化合物が選択使用されており、例えば、アゾ系顔料（
特開昭５４−１４９６７号公報）、無金属フタロシアニ
ン顔料（特開昭６０−１４３３４６号公報）、金属フタ
ロシアニン顔料（特開昭５０−１６５３８号公報）、ス
クェアリウム塩（特開昭５３−２７０３３号公報）等を
挙げることができる。As the organic charge-generating material used in the charge-generating layer, compounds that absorb the energy of irradiated light and efficiently generate charges are selectively used, such as azo pigments (
JP-A-54-14967), metal-free phthalocyanine pigments (JP-A-60-143346), metal phthalocyanine pigments (JP-A-50-16538), squareium salts (JP-A-53-27033) Publications), etc.
電荷輸送層に用いられる電荷輸送材としては、電荷発生
層からの電荷の注入効率が大きく、更に電荷輸送層内で
電荷の移動度が大である化合物を選定する必要がある。As the charge transport material used in the charge transport layer, it is necessary to select a compound that has high charge injection efficiency from the charge generation layer and also has high charge mobility within the charge transport layer.
そのためには、イオン化ポテンシャルが小さい化合物、
ラジカルカチオンが発生しやすい化合物が選ばれ、例え
ばトリアリールアミン誘導体（特開昭５３−４７２６０
号公報）、ヒドラゾン誘導体く特開昭５７−１０１８４
４号公報）、オキサジアゾール誘導体く特公昭３４−５
４６６号公報）、ピラゾリン誘導体（特公昭５２−４１
８８号公報）、スチルベン誘導体（特開昭５８−１９８
０４３号公報）、トリフェニルメタン誘導体（特公昭４
５−５５５号公報）等が提案されている。For this purpose, compounds with small ionization potential,
Compounds that easily generate radical cations are selected, such as triarylamine derivatives (Japanese Patent Application Laid-Open No. 53-47260
Publication No.), hydrazone derivatives JP-A-57-10184
Publication No. 4), Special Publication on Oxadiazole Derivatives, 1973-5
466), pyrazoline derivatives (Japanese Patent Publication No. 52-41
No. 88), stilbene derivatives (JP-A-58-198)
No. 043), triphenylmethane derivatives (Special Publication No. 4
5-555) etc. have been proposed.
しかしながら、これらの電荷移動度は無機物に比較する
と小さいものであり、感度もまだまだ満足できないもの
であった。However, the charge mobility of these materials is small compared to that of inorganic materials, and the sensitivity is still unsatisfactory.
また、帯電、露光、現像、転写、除電という一連の電子
写真プロセスにおいて、感光体は極めて苛酷な条件下に
置かれ、特にその耐オゾン性、耐摩耗性が大きな問題と
なる。Furthermore, in a series of electrophotographic processes such as charging, exposure, development, transfer, and static elimination, the photoreceptor is placed under extremely harsh conditions, and its ozone resistance and abrasion resistance are particularly problematic.
感光体に用いられる材料についても、これら耐久性が要
求される一方、結合剤や保護層についても開発が進んで
いるが、満足できるものは未だ得られていない。Durability is also required for the materials used in the photoreceptor, and while development of binders and protective layers is progressing, a satisfactory material has not yet been obtained.
本発明者らは、上記課題を解決し、高感度、高耐久性の
電子写真感光体を得るべく鋭意検討した結果、特定のト
リヒドラゾン化合物を電荷輸送層中に含む電子写真感光
体が感度、耐久性ともに優れていることを見出し、本発
明を完成するに至った。The present inventors have made intensive studies to solve the above problems and obtain an electrophotographic photoreceptor with high sensitivity and high durability. As a result, an electrophotographic photoreceptor containing a specific trihydrazone compound in the charge transport layer has high sensitivity and They discovered that it has excellent durability and completed the present invention.
即ち本発明は、導電性支持体、電荷発生層及び電荷輸送
層を必須の構成要素とする電子写真感光体において、一
般式（１）
（式中、Ｒ，、Ｒ，’、Ｒ，”は同一もしくは相異なっ
て、水素原子、置換されていてもよい直鎖又は分岐のア
ルキル基、置換されていてもよいアリール基、置換され
ていてもよいアラルキル基のいずれかを表すが、３者が
同時に水素原子となることはない。Ｒ２，Ｒ３＋ Ｒ２
’ 、 Ｒ３’ 、 Ｌ”、 Ｒ３″″は同一もしくは
相異なって、置換されていてもよい直鎖又は分岐のアル
キル基、置換されていてもよいアリール基、置換されて
いてもよいアラルキル基、置換されていてもよい複素環
基のいずれかを表すか、或いはＲ２とＲ３及び／又はＲ
２°とＲ３′ 及び／又はＲ２′″とＲ３″′がそれぞ
れ隣接する窒素原子とともに環を形成する。）
で示されるトリヒドラゾン化合物を電荷輸送層中に含む
ことを特徴とする電子写真感光体を提供するものである
。That is, the present invention provides an electrophotographic photoreceptor having a conductive support, a charge generation layer, and a charge transport layer as essential components, and is provided with the general formula (1) (wherein R,,R,',R,'' is They may be the same or different and represent any one of a hydrogen atom, an optionally substituted linear or branched alkyl group, an optionally substituted aryl group, and an optionally substituted aralkyl group; They cannot become hydrogen atoms at the same time.R2, R3+ R2
', R3', L", R3"" are the same or different and are an optionally substituted linear or branched alkyl group, an optionally substituted aryl group, an optionally substituted aralkyl group, represents any optionally substituted heterocyclic group, or R2 and R3 and/or R
2° and R3' and/or R2'' and R3'' form a ring together with the adjacent nitrogen atom. ) The present invention provides an electrophotographic photoreceptor characterized by containing a trihydrazone compound represented by the following formula in a charge transport layer.
上記一般式（１）で示されるトリヒドラゾン化合物の合
成法は特に限定されるものではなく、例えば４．４’、
４”−トリカルボニル基置換トリフェニルアミンとＮ
、Ｎ−ジ置換ヒドラジン誘導体とを縮合せしめることに
より容易に得ることができる。The method for synthesizing the trihydrazone compound represented by the above general formula (1) is not particularly limited, and for example, 4.4',
4”-tricarbonyl group-substituted triphenylamine and N
, and an N-disubstituted hydrazine derivative.
Ｎ、Ｎ−ジ置換ヒドラジン誘導体は１種のみを用い、４
．４’ 、 ４’″−トリカルボニル基置換トリフェニ
ルアミンに対し３倍モル量を反応させることもできるが
、２種以上を同時に又は添加時期を制御しながら反応さ
せることにより、１分子中に異なるヒドラゾン基を有す
るトリヒドラゾン化合物を得ることができる。Using only one type of N,N-disubstituted hydrazine derivative, 4
．． Although it is possible to react three times the molar amount of 4', 4'''-tricarbonyl group-substituted triphenylamine, by reacting two or more types at the same time or while controlling the timing of addition, it is possible to react with different amounts in one molecule. A trihydrazone compound having a hydrazone group can be obtained.
トリヒドラゾン化合物を含有する電子写真感光体として
は、特開昭５８−１３１９５４号公報に開示されたもの
があるが、そこに示されている化合物は、その原料であ
る４、４’、４”−） ＩＪホルミルトリフェニルアミ
ンの合成が容易ではなく、製造が困難である。これに対
し、本発明に用いられるトリヒドラゾン化合物は合成が
容易な上、感光体としての性能も改良されたものであり
、電子写真感光体により好適に用いることができる。As an electrophotographic photoreceptor containing a trihydrazone compound, there is one disclosed in JP-A-58-131954, and the compound shown therein is 4,4',4'', which is the raw material. -) IJ formyltriphenylamine is not easy to synthesize and is difficult to manufacture.On the other hand, the trihydrazone compound used in the present invention is easy to synthesize and has improved performance as a photoreceptor. Therefore, it can be used more suitably for electrophotographic photoreceptors.
上記一般式（１）において、Ｒ，、Ｒ，’、Ｒ，”は、
同一もしくは相異なって、水素原子、置換されていても
よい直鎖又は分岐のアルキル基、置換されていてもよい
アリール基、置換されていてもよいアラルキル基のいず
れかを表すが、３者が同時に水素原子となることはない
。製造の容易さ、得られた化合物の性能等の点から、水
素原子、炭素数１〜１０個のアルキル基、アリール基、
アラルキル基のいずれかであるものが好ましく、アルキ
ル基、アリール基、アラルキル基としては、例えばメチ
ル基、エチル基、フェニル基、ベンジル基等が例示でき
る。In the above general formula (1), R,,R,',R,'' is
They may be the same or different and represent any one of a hydrogen atom, an optionally substituted linear or branched alkyl group, an optionally substituted aryl group, and an optionally substituted aralkyl group; It cannot become a hydrogen atom at the same time. From the viewpoint of ease of production, performance of the obtained compound, etc., hydrogen atoms, alkyl groups having 1 to 10 carbon atoms, aryl groups,
An aralkyl group is preferred, and examples of the alkyl group, aryl group, and aralkyl group include a methyl group, ethyl group, phenyl group, and benzyl group.
また、一般式（１）において、Ｒ２，Ｒ５，Ｒ２’ 、
Ｒ，”。Furthermore, in general formula (1), R2, R5, R2',
R,”.
Ｒ，”、Ｒ，”は同一もしくは相異なって、置換されて
いてもよい直鎖又は分岐のアルキル基、置換されていて
もよいアリール基、置換されていてもよいアラルキル基
、置換されていてもよい複素環基のいずれかを表すか、
或いはＲ２とＲ３及び／又はＲ２°とＲ３” 及び／又
はＲ２”とＲ３″がそれぞれ隣接する窒素原子とともに
環を形成する。R, ", R," are the same or different and are an optionally substituted linear or branched alkyl group, an optionally substituted aryl group, an optionally substituted aralkyl group, a substituted represents any of the following heterocyclic groups, or
Alternatively, R2 and R3 and/or R2° and R3'' and/or R2'' and R3'' form a ring together with adjacent nitrogen atoms.
これらの中でも、炭素数１〜１２個のアルキル基、了り
−ル基、アラルキル基、複素環基のいずれかであるもの
、或いは隣接する窒素原子とともに炭素数４〜１２個の
環を形成するものが好ましい。Among these, those that are an alkyl group, an aralkyl group, an aralkyl group, or a heterocyclic group having 1 to 12 carbon atoms, or that form a ring with 4 to 12 carbon atoms together with an adjacent nitrogen atom. Preferably.
本発明に用いられるトリヒドラゾン化合物を具体的に例
示すれば、以下の式に示すものが挙げられるが、本発明
はこれらに限定されるものではない。Specific examples of trihydrazone compounds used in the present invention include those represented by the following formulas, but the present invention is not limited thereto.
凸
ｆａｌｌ・ ／・〉
（Ｉ９）
これらのトリヒドラゾン化合物は単独で又は２種以上を
組み合わせて使用することができる。Convex fall・/・> (I9) These trihydrazone compounds can be used alone or in combination of two or more types.
これらトリヒドラゾン化合物は、多くの溶剤に可溶であ
り、例えばベンゼン、トルエン、キシレン、テトラリン
、クロロベンゼン等の芳香族系溶剤；ジクロロメタン、
クロロホルム、トリクロロエチレン、テトラクロロエチ
レン等のハロゲン系溶剤；酢酸メチル、酢酸エチル、酢
酸プロピル、ギ酸メチル、ギ酸エチル等のエステル系溶
剤；アセトン、メチルエチルケトン等のケトン系溶剤；
ジエチルエーテル、ジプロビルエーテノペテトラヒドロ
フラン等のエーテル系溶剤；メタノール、エタノール、
イソプロピルアルコール等のアルコール系溶剤；ジメチ
ルホルムアミド、ジメチルアセトアミド、ジメチルスル
ホキシド等に可溶である。These trihydrazone compounds are soluble in many solvents, such as aromatic solvents such as benzene, toluene, xylene, tetralin, and chlorobenzene; dichloromethane,
Halogen solvents such as chloroform, trichloroethylene, and tetrachloroethylene; Ester solvents such as methyl acetate, ethyl acetate, propyl acetate, methyl formate, and ethyl formate; Ketone solvents such as acetone and methyl ethyl ketone;
Ether solvents such as diethyl ether and dipropylethenotetrahydrofuran; methanol, ethanol,
It is soluble in alcoholic solvents such as isopropyl alcohol; dimethylformamide, dimethylacetamide, dimethylsulfoxide, etc.
電子写真感光体を作製するにあたっては、導電性支持体
上に電荷発生層及び電荷輸送層を薄膜状に形成せしめる
。導電性支持体の基材としては、アルミニウム、ニッケ
ル等の金属、金属蒸着高分子フィルム、金属ラミネート
高分子フィルム等を用いることができ、ドラム状又はシ
ート状の形態で導電性支持体を構成する。In producing an electrophotographic photoreceptor, a charge generation layer and a charge transport layer are formed in the form of a thin film on a conductive support. As the base material of the conductive support, metals such as aluminum and nickel, metal-deposited polymer films, metal-laminated polymer films, etc. can be used, and the conductive support is formed in the form of a drum or sheet. .
電荷発生層は、電荷発生材及び必要に応じて結合剤、添
加剤よりなり、蒸着法、プラズマＣＶＤ法、塗工法等の
方法で作製することができる。The charge generation layer is made of a charge generation material and, if necessary, a binder and additives, and can be produced by a method such as a vapor deposition method, a plasma CVD method, or a coating method.
電荷発生材としては特に限定されることはなく、照射さ
れる特定の波長の光を吸収し、効率よく電荷を発生し得
るものなら有機材料、無機材料のいずれも好適に使用す
ることができる。The charge generating material is not particularly limited, and any organic or inorganic material can be suitably used as long as it absorbs irradiated light of a specific wavelength and can efficiently generate charges.
有機電荷発生材としては、例えばペリレン顔料、多環牛
ノン系顔料、無金属フタロシアニン顔料、金属フタロシ
アニン顔料、ビスアゾ顔料、トリスアゾ顔料、チアピリ
リウム塩、スクェアリウム塩、アズレニウム顔料等があ
げられ、これらは主として結合剤中に分散せしめ、塗工
により電荷発生層を形成することができる。無機電荷発
生材としては、セレン、セレン合金、硫化カドミウム、
酸化亜鉛、アモルファスシリコン等があげられる。Examples of organic charge generating materials include perylene pigments, polycyclic bovine pigments, metal-free phthalocyanine pigments, metal phthalocyanine pigments, bisazo pigments, trisazo pigments, thiapyrylium salts, squareium salts, azulenium pigments, etc. A charge generation layer can be formed by dispersing it in a binder and coating it. Inorganic charge generating materials include selenium, selenium alloys, cadmium sulfide,
Examples include zinc oxide and amorphous silicon.
形成された電荷発生層の膜厚は０．１乃至２．０μｍが
好ましく、さらに好ましくは０．２乃至１．０μｍであ
る。The thickness of the formed charge generation layer is preferably 0.1 to 2.0 μm, more preferably 0.2 to 1.0 μm.
次に該電荷発生層の上部に一般式（１）で示されるトリ
ヒドラゾン化合物を含む電荷輸送層を薄膜状に形成せし
める。薄膜形成法としては主に塗工法が用いられ、一般
式（１）で示されるトリヒドラゾン化合物を必要に応じ
て結合剤とともに溶剤に溶解し、電荷発生層上に塗工せ
しめ、その後乾燥させればよい。用いられる溶剤として
は、上記トリヒドラゾン化合物及び必要に応じて用いら
れる結合剤が溶解し、かつ電荷発生層が溶解しない溶剤
なら、特に限定されることはない。Next, a charge transport layer containing a trihydrazone compound represented by the general formula (1) is formed in the form of a thin film on top of the charge generation layer. A coating method is mainly used to form a thin film, in which a trihydrazone compound represented by the general formula (1) is dissolved in a solvent together with a binder if necessary, coated on the charge generation layer, and then dried. Bye. The solvent to be used is not particularly limited as long as it dissolves the trihydrazone compound and the optional binder and does not dissolve the charge generation layer.
必要に応じて用いられる結合剤は、絶縁性樹脂なら特に
限定されることはな（、例えばポリカーボネート、ボリ
アリレート、ポリエステノベポリアミド等の縮合系重合
体；ポリエチレン、ポリスチレン、スチレン−アクリル
共重合体、ポリアクリレート、ポリメタクリレート、ポ
リビニルブチラール、ポリアクリロニトリル、ポリアク
リルアミド、アクリロニトリル−ブタジェン共重合体、
ポリ塩化ビニル等の付加重合体；ポリスルホン、ポリエ
ーテルスルホン、シリコン樹脂等が適宜用いられ、１種
もしくは２種以上のものを混合して用いることができる
。The binder used as necessary is not particularly limited as long as it is an insulating resin (e.g., condensation polymers such as polycarbonate, polyarylate, polyesternovepolyamide; polyethylene, polystyrene, styrene-acrylic copolymer, etc.). Polyacrylate, polymethacrylate, polyvinyl butyral, polyacrylonitrile, polyacrylamide, acrylonitrile-butadiene copolymer,
Addition polymers such as polyvinyl chloride; polysulfone, polyethersulfone, silicone resin, etc. are used as appropriate, and one type or a mixture of two or more types can be used.
上記結合剤の使用量は一般式（１）で示されるトリヒド
ラゾン化合物に対して０．１乃至３重量比であり、好ま
しくは０．１乃至２重量比である。The amount of the binder used is 0.1 to 3 weight ratio, preferably 0.1 to 2 weight ratio with respect to the trihydrazone compound represented by general formula (1).
結合剤の量がこれよりも大であると、電荷輸送層におけ
る電荷輸送材濃度が小さくなり、感度が悪くなる。If the amount of binder is greater than this, the concentration of the charge transport material in the charge transport layer will be low, resulting in poor sensitivity.
また、本発明においては、必要に応じて前記のような公
知の電荷輸送材を組み合わせて用いることも可能である
。Further, in the present invention, it is also possible to use a combination of known charge transport materials as described above, if necessary.
電荷輸送層の塗工手段は限定されることはなく、例エバ
バーコーター、カレンダーコーター、グラビアコーター
、ブレードコーター、スピンコーター、デイツプコータ
ー等を適宜使用することができる。The means for coating the charge transport layer is not limited, and examples of suitable methods include an Evervar coater, a calendar coater, a gravure coater, a blade coater, a spin coater, a dip coater, and the like.
このようにして形成される電荷輸送層の膜厚は１０乃至
５０μｍが好ましく、更に好ましくは１０乃至３０μｍ
である。膜厚が５０μｍよりも大であると、電荷の輸送
により多くの時間を要するようになり、また、電荷が捕
獲される確率も大となり、感度低下の原因となる。一方
、１０μｍより小であると、機械的強度が低下し、感光
体の寿命が短いものとなり好ましくない。The thickness of the charge transport layer formed in this way is preferably 10 to 50 μm, more preferably 10 to 30 μm.
It is. If the film thickness is greater than 50 μm, it will take more time to transport the charges, and the probability that the charges will be captured will also increase, causing a decrease in sensitivity. On the other hand, if it is smaller than 10 μm, the mechanical strength will decrease and the life of the photoreceptor will be shortened, which is not preferable.
以上の如くにして一般式（１）で示されるトリヒドラゾ
ン化合物を電荷輸送層に含む電子写真感光体を作製する
ことができるが、本発明ではさらに導電性支持体と電荷
発生層の間に必要に応じて下引き層、接着層、バリヤー
層等を設けることもでき、これらの層には、例えばポリ
ビニルブチラーノペフェノール樹脂、ポリアミド樹脂等
が用いられる。また、感光体表面に表面保護層を設ける
こともできる。As described above, an electrophotographic photoreceptor containing a trihydrazone compound represented by the general formula (1) in the charge transport layer can be produced. An undercoat layer, adhesive layer, barrier layer, etc. may be provided depending on the requirements, and these layers may be made of, for example, polyvinyl butyranopephenol resin, polyamide resin, or the like. Furthermore, a surface protective layer can also be provided on the surface of the photoreceptor.
こうして得られた電子写真感光体の使用に際しては、ま
ず感光体表面をコロナ帯電器等により負に帯電せしめる
。帯電後、露光されることにより電荷発生層内で電荷が
発生し、正電荷が電荷輸送層に注入され、これが電荷輸
送層中を通って表面にまで輸送され、表面の負電荷が中
和される。一方、露光されなかった部分には負電荷が残
り、これが静電潜像を形成する。この部分にトナーが付
着し、それが紙等の上に転写され定着される。When using the electrophotographic photoreceptor thus obtained, first the surface of the photoreceptor is negatively charged using a corona charger or the like. After being charged, charges are generated in the charge generation layer by exposure to light, and positive charges are injected into the charge transport layer, which are transported through the charge transport layer to the surface, neutralizing the negative charges on the surface. Ru. On the other hand, negative charges remain in the unexposed areas, which form an electrostatic latent image. Toner adheres to this area, and is transferred and fixed onto paper or the like.
また、本発明においては、導電性支持体上に、まず電荷
輸送層を設け、その上に電荷発生層を設けて電子写真感
光体を作製することも可能である。この場合には、まず
感光体表面を正に帯電せしめ、露光後、発生した負電荷
は感光体の表面電荷を中和し、正電荷は電荷輸送層を通
って導電性支持体に輸送されることになる。Further, in the present invention, it is also possible to produce an electrophotographic photoreceptor by first providing a charge transport layer on a conductive support and then providing a charge generation layer thereon. In this case, the surface of the photoreceptor is first positively charged, and after exposure, the generated negative charges neutralize the surface charges of the photoreceptor, and the positive charges are transported to the conductive support through the charge transport layer. It turns out.
以下、実施例により本発明を具体的に説明するが、本発
明はこれら実施例に限定されるものではない。EXAMPLES Hereinafter, the present invention will be specifically explained with reference to Examples, but the present invention is not limited to these Examples.
合成例
４．４°、４” −） ＩＪアセチルトリフェニルアミ
ン−撹拌装置、温度計、冷却管のついた脱水管を備えつ
けた１１三ツロフラスコに４，４°、４”−トリアセチ
ルトリフェニルアミン３．７ｇ（１０ミリモル）、Ｎ、
Ｎ−ジフェニルヒドラジン塩酸塩６．６ｇ（３０ミリモ
ル）、ｐ−）ルエンスルホン酸０．１ｇを入れ、ベンゼ
ン５００ｒｄに溶解させた。その後加熱還流を１２時間
行ったところ、縮合水が約０．５ｍｌ留出した。反応混
合物を室温にまで冷却した後、飽和炭酸水素ナトリウム
水溶液１１で２回、水で１回洗浄した。ベンゼン溶液を
無水硫酸す）ＩＪウムで乾燥した後、ベンゼンを留去し
、残った固体をヘキサン／酢酸エチル（４／１）より再
結晶させ、４．４’ 、 ４”−トリアセチルトリフェ
ニルアミン−トリス（Ｎ、Ｎ ”フェニルヒドラゾン
） ７．４ｇ （収率８５％）を得た。Synthesis Example 4.4°, 4”-) IJ acetyltriphenylamine - 4.4°, 4”-triacetyltriphenylamine in a 11 three-tube flask equipped with a stirrer, a thermometer, and a dehydration tube with a condenser. 3.7 g (10 mmol), N,
6.6 g (30 mmol) of N-diphenylhydrazine hydrochloride and 0.1 g of p-)luenesulfonic acid were added and dissolved in 500 rd benzene. Thereafter, the mixture was heated under reflux for 12 hours, and about 0.5 ml of condensed water was distilled out. After the reaction mixture was cooled to room temperature, it was washed twice with saturated aqueous sodium bicarbonate solution 11 and once with water. After drying the benzene solution over anhydrous sulfuric acid, the benzene was distilled off and the remaining solid was recrystallized from hexane/ethyl acetate (4/1) to give 4.4', 4''-triacetyltriphenyl. 7.4 g (85% yield) of amine-tris(N,N'' phenylhydrazone) was obtained.
実施例１
バナジルフタロシアニン５ｇ１ブチラール樹脂（エスレ
ック８Ｍ−２、漬水化学■ｍ）５ｇをシクロへキサノン
９０ｍｊ’に溶解し、ボールミル中で２４時間混練した
。得られた分散液をアルミ板上にバーコーターにて乾燥
後の膜厚が０．５μｍとなるように塗布し、乾燥させ、
電荷発生層を形成した。Example 1 5 g of vanadyl phthalocyanine and 5 g of butyral resin (S-LEC 8M-2, Tsukisui Kagaku ■m) were dissolved in 90 mj' of cyclohexanone and kneaded in a ball mill for 24 hours. The obtained dispersion was applied onto an aluminum plate using a bar coater so that the film thickness after drying was 0.5 μm, and dried.
A charge generation layer was formed.
次に合成例により得た４、４°、４”−トリアセチルト
リフェニルアミン−トリス（Ｎ、 Ｎ−ジフェニルヒド
ラゾン）５ｇ１ポリカーボネート樹脂（レキサン１４１
−１１１ 、エンジニアリングプラスチックス■製）５
ｇを塩化メチレン９０ｍｔ’に溶解し、これを先に形成
した電荷発生層上にブレードコーターにて乾燥後の膜厚
が２５μｍになるように塗布して乾燥させ、電荷輸送層
を形成した。Next, 5 g of 4,4°,4”-triacetyltriphenylamine-tris (N, N-diphenylhydrazone) obtained in the synthesis example, 1 polycarbonate resin (Lexan 141
-111, manufactured by Engineering Plastics) 5
g was dissolved in 90 mt' of methylene chloride, and this was applied onto the previously formed charge generation layer using a blade coater so that the film thickness after drying would be 25 μm and dried to form a charge transport layer.
このようにして作製した電子写真感光体を■川口電機製
作所製静電複写紙試験装置５Ｐ−４２８を用いて−５，
５ｋＶのコロナ電圧で帯電させたところ、初期表面電位
Ｖ。は−７３０ｖであった。暗所にて５秒放置後の表面
電位ｖ５は一７２０ｖとなった。The electrophotographic photoreceptor thus produced was tested using an electrostatic copying paper tester 5P-428 manufactured by Kawaguchi Electric Seisakusho.
When charged with a corona voltage of 5 kV, the initial surface potential was V. was -730v. After being left in the dark for 5 seconds, the surface potential v5 was -720V.
次いで、発振波長７８０ｎｍの半導体レーザーを照射し
、半減露光ＭｔＥ、ｙ□を求めたところ０．５μＪ／ｃ
ｍ ２であり、残留電位Ｖ、は−８，２ｖであった。Next, a semiconductor laser with an oscillation wavelength of 780 nm was irradiated, and the half-exposure MtE,y□ was determined to be 0.5 μJ/c.
m2, and the residual potential V was -8.2v.
次に、５０００回上記操作を繰り返した後、ｖｏ。Next, after repeating the above operation 5000 times, vo.
ＶＳ＋ Ｅｌ／２． ＶＲを測定したところ、それぞれ
−７２０Ｖ、 −７１５Ｖ、 ０，５μＪ／ｃｍ２．
−３，３Ｖであり、感光体としての性能は殆ど衰えて
おらず、高い耐久性を示すことがわかった。VS+ El/2. When VR was measured, they were -720V, -715V, and 0.5μJ/cm2, respectively.
-3.3V, and it was found that the performance as a photoreceptor had hardly deteriorated and exhibited high durability.
実施例２〜５
電荷輸送材として、それぞれ表−１に示した化合物を用
いる以外は、実施例１と同様にして感光体を作製し、性
能評価を行った。その結果を表−１に示した。Examples 2 to 5 Photoreceptors were produced in the same manner as in Example 1, except that the compounds shown in Table 1 were used as charge transport materials, and performance evaluation was performed. The results are shown in Table-1.
表−１
実施例６
実施例１において、バナジルフタロシアニンの代わりに
Ｘ型無金属フタロシアニンを用いる以外は全く同様にし
て感光体を作製し、性能評価を行った。Table 1 Example 6 A photoreceptor was produced in exactly the same manner as in Example 1 except that X-type metal-free phthalocyanine was used instead of vanadyl phthalocyanine, and performance evaluation was performed.
初期表面電位Ｖ。は−７１０ｖであり、暗所にて５秒放
置後の表面電位ｖ５は一７０５ｖとなった。発振波長７
８０ｎｍの半導体レーザーを照射したときの半減露光量
Ｅ、／２は０．６μＪ／ｃｍ２であり、残留電位ＶＲは
−１２，ＯＶ テアツタ。Initial surface potential V. was -710v, and the surface potential v5 after being left in the dark for 5 seconds was -705v. Oscillation wavelength 7
When irradiated with a semiconductor laser of 80 nm, the half-decreased exposure amount E, /2 is 0.6 μJ/cm2, and the residual potential VR is -12, OV.
また、５０００回上記操作を繰り返した後のＶ。。Also, V after repeating the above operation 5000 times. .
ｖＳ＋ Ｅｌ／２． Ｖｉハ、それぞれ−７００Ｖ、
−６８０Ｖ、 ０．６μＪ／ｃｍ２． −１２．５Ｖ
であり、感光体としての性能は殆ど衰えておらず、高い
耐久性を示した。vS+ El/2. Viha, -700V each,
-680V, 0.6μJ/cm2. -12.5V
The performance as a photoreceptor showed almost no decline and showed high durability.
比較例
実施例１において、式（２）で示されるトリヒドラゾン
化合物の代わりに、次式で示されるヒドラゾン化合物を
用いる以外は、全く同様にして感光体を作製し、評価を
行った。Comparative Example A photoreceptor was prepared and evaluated in exactly the same manner as in Example 1, except that a hydrazone compound represented by the following formula was used instead of the trihydrazone compound represented by formula (2).
露光前の表面電位はＶ。＝−７７０Ｖ、 ｖｓ＝−７５
０ｖであり、前述の実施例１〜５と差は見られなかった
が、εＩ／２ ＝２．１ ｔ−ｔＪ／ｃｍ”であり、半
減露光量が悪いものであった。また、残留電位もＶＲ＝
−３２Ｖと大きな値を示した。The surface potential before exposure is V. =-770V, vs=-75
0 V, and no difference was observed from the above-mentioned Examples 1 to 5, but εI/2 = 2.1 t-tJ/cm'', which was a poor half-decreased exposure amount. Also VR=
It showed a large value of -32V.
本発明におけるトリヒドラゾン化合物を電荷輸送層中に
含むことを特徴とする電子写真感光体は、初期電位が安
定し、暗減衰が小さく、感度が高いものである。また、
繰り返しによる劣化が小さく、耐久性にも優れたもので
ある。The electrophotographic photoreceptor of the present invention, which is characterized by containing a trihydrazone compound in its charge transport layer, has a stable initial potential, small dark decay, and high sensitivity. Also,
It shows little deterioration due to repeated use and has excellent durability.
出願人代理人 古 谷 馨Applicant's agent Kaoru Furutani
Claims (1)
構成要素とする電子写真感光体において、一般式（１） ▲数式、化学式、表等があります▼（１） （式中、Ｒ＿１、Ｒ＿１’、Ｒ＿１”は同一もしくは相
異なって、水素原子、置換されていてもよい直鎖又は分
岐のアルキル基、置換されていてもよいアリール基、置
換されていてもよいアラルキル基のいずれかを表すが、
３者が同時に水素原子となることはない。Ｒ＿２、Ｒ＿
３、Ｒ＿２’、Ｒ＿３’、Ｒ＿２”、Ｒ＿３”は同一も
しくは相異なって、置換されていてもよい直鎖又は分岐
のアルキル基、置換されていてもよいアリール基、置換
されていてもよいアラルキル基、置換されていてもよい
複素環基のいずれかを表すか、或いはＲ＿２とＲ＿３及
び／又はＲ＿２’とＲ＿３’及び／又はＲ＿２”とＲ＿
３”がそれぞれ隣接する窒素原子とともに環を形成する
。） で示されるトリヒドラゾン化合物を電荷輸送層中に含む
ことを特徴とする電子写真感光体。[Scope of Claims] 1. In an electrophotographic photoreceptor having a conductive support, a charge generation layer, and a charge transport layer as essential components, general formula (1) ▲Mathematical formula, chemical formula, table, etc.▼(1) (In the formula, R_1, R_1', R_1'' are the same or different and each represents a hydrogen atom, an optionally substituted linear or branched alkyl group, an optionally substituted aryl group, an optionally substituted Represents any aralkyl group,
All three cannot become hydrogen atoms at the same time. R_2, R_
3. R_2', R_3', R_2'', and R_3'' are the same or different and are an optionally substituted linear or branched alkyl group, an optionally substituted aryl group, an optionally substituted aralkyl group group, an optionally substituted heterocyclic group, or R_2 and R_3 and/or R_2' and R_3' and/or R_2'' and R_
3'' forms a ring together with adjacent nitrogen atoms.) An electrophotographic photoreceptor comprising a trihydrazone compound represented by:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12930588A JPH01298364A (en) | 1988-05-26 | 1988-05-26 | Electrophotographic sensitive body |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12930588A JPH01298364A (en) | 1988-05-26 | 1988-05-26 | Electrophotographic sensitive body |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH01298364A true JPH01298364A (en) | 1989-12-01 |
Family
ID=15006278
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12930588A Pending JPH01298364A (en) | 1988-05-26 | 1988-05-26 | Electrophotographic sensitive body |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01298364A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5246808A (en) * | 1991-03-19 | 1993-09-21 | Mita Industrial Co., Ltd. | Hydrazone compound and photosensitive material using said compound |
| CN105294540A (en) * | 2015-11-25 | 2016-02-03 | 齐鲁工业大学 | Novel Schiff base compound taking triphenylamine as center and preparation of novel Schiff base compound |
-
1988
- 1988-05-26 JP JP12930588A patent/JPH01298364A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5246808A (en) * | 1991-03-19 | 1993-09-21 | Mita Industrial Co., Ltd. | Hydrazone compound and photosensitive material using said compound |
| CN105294540A (en) * | 2015-11-25 | 2016-02-03 | 齐鲁工业大学 | Novel Schiff base compound taking triphenylamine as center and preparation of novel Schiff base compound |
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