JPH0454226B2 - - Google Patents
Info
- Publication number
- JPH0454226B2 JPH0454226B2 JP63111250A JP11125088A JPH0454226B2 JP H0454226 B2 JPH0454226 B2 JP H0454226B2 JP 63111250 A JP63111250 A JP 63111250A JP 11125088 A JP11125088 A JP 11125088A JP H0454226 B2 JPH0454226 B2 JP H0454226B2
- Authority
- JP
- Japan
- Prior art keywords
- electrophotographic photoreceptor
- electrophotographic
- charge
- general formula
- potential
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/135—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- 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 or 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
- G03G5/0614—Amines
- G03G5/06142—Amines arylamine
- G03G5/06147—Amines arylamine alkenylarylamine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
- C07C211/56—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/58—Naphthylamines; N-substituted derivatives thereof
-
- 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 or 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
- G03G5/0614—Amines
- G03G5/06142—Amines arylamine
- G03G5/06144—Amines arylamine diamine
- G03G5/061443—Amines arylamine diamine benzidine
-
- 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 or 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
- G03G5/0614—Amines
- G03G5/06142—Amines arylamine
- G03G5/06147—Amines arylamine alkenylarylamine
- G03G5/061473—Amines arylamine alkenylarylamine plural alkenyl groups linked directly to the same aryl group
-
- 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 or 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
- G03G5/0618—Acyclic or carbocyclic compounds containing oxygen and nitrogen
-
- 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 or 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
- G03G5/0622—Heterocyclic compounds
- G03G5/0624—Heterocyclic compounds containing one hetero ring
- G03G5/0627—Heterocyclic compounds containing one hetero ring being five-membered
- G03G5/0629—Heterocyclic compounds containing one hetero ring being five-membered containing one hetero atom
-
- 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 or 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
- G03G5/0622—Heterocyclic compounds
- G03G5/0624—Heterocyclic compounds containing one hetero ring
- G03G5/0635—Heterocyclic compounds containing one hetero ring being six-membered
- G03G5/0637—Heterocyclic compounds containing one hetero ring being six-membered containing one hetero atom
-
- 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 or 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
- G03G5/0622—Heterocyclic compounds
- G03G5/0624—Heterocyclic compounds containing one hetero ring
- G03G5/0635—Heterocyclic compounds containing one hetero ring being six-membered
- G03G5/0638—Heterocyclic compounds containing one hetero ring being six-membered containing two hetero atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Photoreceptors In Electrophotography (AREA)
Description
〔産業上の利用分野〕
本発明は、電子写真感光体に関し、詳しくは改
善された電子写真特性を与える低分子の有機光導
電体を含有する電子写真感光体に関するものであ
る。
〔従来技術〕
従来、電子写真感光体で用いる光導電材料とし
て、セレン、流化カドミウム、酸化亜鉛などの無
機光導電性材料が知られている。これらの光導電
性材料は、数多くの利点、例えば暗所で適当な電
位に帯電できること、暗所で電荷の逸散が少ない
こと、あるいは光照射によつて速やかに電荷を逸
散できることなどの利点をもつている反面、各種
の欠点を有している。例えば、セレン系感光体で
は、温度、湿度、ごみ、圧力などの要因で容易に
結晶化が進み、特に雰囲気温度が40℃を越えると
結晶化が著しくなり、帯電性の低下や画像に白い
斑点が発生するといつた欠点がある。流化カドミ
ウム系感光体は、多湿の環境下で安定した感度が
得られない。酸化亜鉛系感光体ではローズベンガ
ルに代表される増感色素による増感効果を必要と
しているが、この様な増感色素がコロナ帯電によ
る帯電劣化や露光光による光退色を生じるため長
期に亘つて安定した画像を与えることができない
欠点を有している。
一方、ポリビニルカルバゾールをはじめとする
各種の有機光導電性ポリマーが提案されて来た
が、これらのポリマーは、前述の無機系光導電材
料に較べ成膜性、軽量性などの点で優れているに
もかかわらず今日までその実用化が困難であつ
た。それは、未だ十分な成膜性が得られておら
ず、また感度、耐久性および環境変化による安定
性の点で無機系光導電材料に較べ劣つているため
であつた。また、米国特許第4150987号公報など
に開示のヒドラゾン化合物、米国特許第3837851
号公報などに記載のトリアリールピラゾリン化合
物、特開昭51−94828号公報、特開昭51−94829号
公報などに記載の９−スチリルアントラセン化合
物などの低分子の有機光導電体が提案されてい
る。この様な低分子の有機光導電体は、使用する
バインダーを適当に選択する事によつて、有機光
導電性ポリマーの分野で問題となつていた成膜性
の欠点を解消できる様になつたが、感度の点で十
分なものとは言えない。
このようなことから、近年感光層を電荷発生層
と電荷輸送層に機能分離させた積層構造体が知ら
れている。この積層構造を感光層とした電子写真
感光体は、可視光に対する感度、電荷保持力、表
面強度などの点で改善できるようになつた。この
ような電子写真感光体は、例えば米国特許第
3837851号、同第3871882号公報などに開示されて
いる。
しかし、従来の低分子の有機光導電体を電荷輸
送層に用いた電子写真感光体では、感度、特性が
必らずしも十分でなく、特に繰り返し帯電および
露光を行なつた際には明部電位と暗部電位の変動
が大きく、改善すべき点がある。
〔発明が解決しようとする問題点〕
本発明の目的は前述の欠点又は不利を解消した
電子写真感光体を提供することにある。
本発明の他の目的は、電荷発生層と電荷輸送層
に機能分離した積層型感光層における新規な電荷
輸送物質を提供することにある。
〔問題点を解決するための手段〕
本発明のかかる目的は、一般式（）で示され
るアミン化合物を含有する層を有する電子写真感
光体によつて達成される。
一般式
式中R1，R2，R3，R4，R5およびR6はメチル、
エチル、プロピル、ブチル等のアルキル基、ベン
ジル、フエネチル、ナフチルメチル等のアラルキ
ル基、またはフエニル、ビフエニル、ナフチル等
のアリール基でいずれの基も置換基を有していて
も良い。
R1，R2，R3，R4，R5およびR6に用いられる置
換基としては、フツ素、塩素、臭素、沃素のハロ
ゲン原子、メチル、エチル、プロピル、ブチル等
のアルキル基、メトキシ、エトキシ、プロポキシ
等のアルコキシ基、フエニルオキシ基、又はジメ
チルアミノ、ジエチルアミノ、ジフエニルアミ
ノ、ジトリルアミノ、ジメトキシフエニルアミ
ノ、ピペリジノ、ピペラジノ等の置換アミノ基等
が挙げられる。
以下に一般式（）で示す化合物についての代
表例を挙げる。
一般式
[Industrial Field of Application] The present invention relates to an electrophotographic photoreceptor, and more particularly to an electrophotographic photoreceptor containing a low molecular weight organic photoconductor that provides improved electrophotographic properties. [Prior Art] Conventionally, inorganic photoconductive materials such as selenium, fluidized cadmium, and zinc oxide are known as photoconductive materials used in electrophotographic photoreceptors. These photoconductive materials have a number of advantages, such as being able to be charged to an appropriate potential in the dark, having little charge dissipation in the dark, or being able to quickly dissipate the charge when irradiated with light. However, it also has various drawbacks. For example, selenium-based photoreceptors easily crystallize due to factors such as temperature, humidity, dust, and pressure. Especially when the ambient temperature exceeds 40°C, crystallization becomes significant, resulting in decreased charging performance and white spots on images. There is a drawback when this occurs. Fluidized cadmium-based photoreceptors cannot provide stable sensitivity in humid environments. Zinc oxide photoreceptors require the sensitizing effect of sensitizing dyes, such as rose bengal, but these sensitizing dyes cause charge deterioration due to corona charging and photobleaching due to exposure light, so they cannot be used for long periods of time. It has the disadvantage that it cannot provide stable images. On the other hand, various organic photoconductive polymers including polyvinylcarbazole have been proposed, but these polymers are superior in terms of film formability and lightness compared to the inorganic photoconductive materials mentioned above. However, until now it has been difficult to put it into practical use. This is because sufficient film-forming properties have not yet been obtained, and they are inferior to inorganic photoconductive materials in terms of sensitivity, durability, and stability against environmental changes. In addition, hydrazone compounds disclosed in U.S. Patent No. 4150987, etc., and U.S. Patent No. 3837851
Low-molecular organic photoconductors have been proposed, such as triarylpyrazoline compounds described in JP-A-51-94828, 9-styrylanthracene compounds described in JP-A-51-94829, etc. ing. By appropriately selecting the binder used, such low-molecular-weight organic photoconductors can overcome the drawbacks of film-forming properties that have been a problem in the field of organic photoconductive polymers. However, it cannot be said to be sufficient in terms of sensitivity. For this reason, in recent years, laminated structures have been known in which the photosensitive layer is functionally separated into a charge generation layer and a charge transport layer. Electrophotographic photoreceptors using this laminated structure as a photosensitive layer can now be improved in terms of sensitivity to visible light, charge retention, surface strength, and the like. Such an electrophotographic photoreceptor is disclosed in, for example, US Pat.
It is disclosed in Publication No. 3837851, Publication No. 3871882, etc. However, electrophotographic photoreceptors that use conventional low-molecular organic photoconductors in the charge transport layer do not always have sufficient sensitivity and characteristics, especially when repeatedly charged and exposed. There are large fluctuations in the part potential and dark part potential, and there are points that need improvement. [Problems to be Solved by the Invention] An object of the present invention is to provide an electrophotographic photoreceptor that eliminates the above-mentioned drawbacks or disadvantages. Another object of the present invention is to provide a novel charge transport material in a laminated photosensitive layer in which a charge generation layer and a charge transport layer are functionally separated. [Means for Solving the Problems] This object of the present invention is achieved by an electrophotographic photoreceptor having a layer containing an amine compound represented by the general formula (). general formula In the formula, R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are methyl,
Any of the alkyl groups such as ethyl, propyl and butyl, aralkyl groups such as benzyl, phenethyl and naphthylmethyl, and aryl groups such as phenyl, biphenyl and naphthyl may have a substituent. Substituents used for R 1 , R 2 , R 3 , R 4 , R 5 and R 6 include halogen atoms such as fluorine, chlorine, bromine and iodine, alkyl groups such as methyl, ethyl, propyl and butyl, methoxy , ethoxy, propoxy, and other alkoxy groups, phenyloxy groups, and substituted amino groups such as dimethylamino, diethylamino, diphenylamino, ditolylamino, dimethoxyphenylamino, piperidino, and piperazino. Representative examples of compounds represented by the general formula () are listed below. general formula
【表】【table】
【表】
上記アミン化合物の合成は、一般的にアミン
[Table] The synthesis of the above amine compounds is generally carried out using amines.
【式】と[Formula] and
【式】
とを当モル、ウルマン反応させ、中間体一般式
（）
を単離し、中間体（）と
[Formula] is subjected to an equimolar Ullmann reaction, and the intermediate general formula () is obtained. Isolate the intermediate () and
以下、本発明を実施例に従つて説明する。
実施例 １
β型銅フタロシアニン（商品名Lionol Blue
NCB Toner 東洋インキ製造(株)製の）を水、エ
タノールおよびベンゼン中で順次還流後、濾過し
て精製した顔料7g；ポリエステル「商品名：ポ
リエステルアドヒーシブ49000（固形分20％）デユ
ポン社製」14g；トルエン35g；ジオキサン35gを
混合し、ボールミルで６時間分散することによつ
て塗工液を調製した。この塗工液をアルミニウム
シート上に乾燥膜厚が0.5μmとなる様にマイヤー
バーで塗布して電荷発生層を形成した。
次に、電荷輸送物質として前記例示化合物−
１を7gとポリカーボネート樹脂（商品名パンラ
イトＫ−1300帝人化成(株)製）7gとをテトラヒド
ロフラン35gとクロロベンゼン35gの混合溶媒中
に攪拌溶解させて得た溶液を先の電荷発生層の上
に、マイヤーバーで乾燥膜厚が16μmとなる様に
塗工して、二層構造からなる感光層をもつ電子写
真感光体を製造した。
この様にして製造した電子写真感光体を川口電
機(株)製静電複写紙試験装置Model−SP−428を用
いてスタチツク方式で−5KVでコロナ帯電し、
暗所で１秒間保持した後、照度2.5uxで露光し
帯電特性を調べた。
帯電特性としては、表面電位V0と１秒間暗減
衰させた時の電位V1を1/2に減衰するに必要な露
光量Ｅ1/2を測定した。
さらに、繰り返し使用した時の明部電位と暗部
電位の変動を測定するために、本実施例で製造し
た電子写真感光体をキヤノン(株)製PPC複写機NP
−150Zの感光ドラム用シリンダーに貼り付けて、
同機で50000枚複写を行ない、初期と50000枚複写
後の明部電位VL及び暗部電位VDの変動を測定し
た。
また前記例示化合物の代りに下記構造式
のアミン化合物を用いて全く同様の操作によ
り、比較試料−１及び−２を製造し、同様に測定
した。
この結果を次に示す。
Hereinafter, the present invention will be explained according to examples. Example 1 β-type copper phthalocyanine (trade name: Lionol Blue)
NCB Toner (manufactured by Toyo Ink Mfg. Co., Ltd.) 7g of pigment purified by refluxing it in water, ethanol and benzene sequentially and filtering it; Polyester "Product name: Polyester Adhesive 49000 (solid content 20%)" Manufactured by Dupont A coating solution was prepared by mixing 14 g of "14 g", 35 g of toluene, and 35 g of dioxane, and dispersing the mixture in a ball mill for 6 hours. This coating solution was applied onto an aluminum sheet using a Mayer bar to a dry film thickness of 0.5 μm to form a charge generation layer. Next, the above-mentioned exemplified compound -
1 and 7 g of polycarbonate resin (trade name: Panlite K-1300, manufactured by Teijin Kasei Ltd.) were stirred and dissolved in a mixed solvent of 35 g of tetrahydrofuran and 35 g of chlorobenzene, and a solution obtained was placed on the charge generation layer. An electrophotographic photoreceptor having a photosensitive layer having a two-layer structure was manufactured by coating the film with a Mayer bar to a dry film thickness of 16 μm. The electrophotographic photoreceptor produced in this manner was statically charged with corona at -5 KV using an electrostatic copying paper tester Model-SP-428 manufactured by Kawaguchi Electric Co., Ltd.
After holding it in a dark place for 1 second, it was exposed to light at an illuminance of 2.5ux to examine the charging characteristics. As for charging characteristics, the surface potential V 0 and the exposure amount E 1/2 required to attenuate the potential V 1 by 1/2 when dark decaying for 1 second were measured. Furthermore, in order to measure the fluctuations in bright area potential and dark area potential during repeated use, the electrophotographic photoreceptor manufactured in this example was used in a PPC copier NP manufactured by Canon Inc.
Attach it to the -150Z photosensitive drum cylinder,
The same machine made 50,000 copies, and the fluctuations in the bright area potential V L and the dark area potential V D were measured at the initial stage and after 50,000 copies were made. In addition, the following structural formula can be used instead of the above-mentioned exemplified compounds. Comparative samples -1 and -2 were prepared using the same amine compound and measured in the same manner. The results are shown below.
【表】
この結果からも本発明になる化合物は高感度で
あり、かつ耐久安定性にも優れた感光体を形成す
ることが判る。
実施例 ２〜９
この各実施例においては、前記実施例１で用い
た電荷輸送物質として例示化合物−１の代りに
例示した化合物２，３，４，６，９，10，12，14
を用い、かつ電荷発生物質として例示−（21）
の顔料を用いたほかは、実施例１と同様の方法に
よつて電子写真感光体を製造した。
各感光体の電子写真特性を実施例１と同様の方
法によつて測定した。その結果を次に示す。[Table] This result also shows that the compounds of the present invention form photoreceptors with high sensitivity and excellent durability and stability. Examples 2 to 9 In each of these Examples, Compounds 2, 3, 4, 6, 9, 10, 12, 14 were used instead of Exemplified Compound-1 as the charge transport substance used in Example 1.
and as an example of a charge generating substance - (21)
An electrophotographic photoreceptor was produced in the same manner as in Example 1, except that the following pigment was used. The electrophotographic properties of each photoreceptor were measured in the same manner as in Example 1. The results are shown below.
本発明の電子写真感光体は、特定のヒドラゾン
化合物を電荷輸送物質として使用することによ
り、高感度、高耐久（繰り返し使用による電位変
動が著しく少ない）で、しかも電子写真利用分野
の広範囲に適用できるという顕著な効果を奏する
ものである。
By using a specific hydrazone compound as a charge transport material, the electrophotographic photoreceptor of the present invention has high sensitivity and durability (significantly less potential fluctuation due to repeated use), and can be applied to a wide range of electrophotographic fields. This has a remarkable effect.
Claims (1)
する層を有することを特徴とする電子写真感光
体。 一般式 〔ただし、式中R1，R2，R3，R4，R5およびR6
は置換基を有していても良いアルキル基、アラル
キル基またはアリール基を示す。〕[Scope of Claims] 1. An electrophotographic photoreceptor comprising a layer containing an amine compound represented by the general formula (). general formula [However, in the formula R 1 , R 2 , R 3 , R 4 , R 5 and R 6
represents an alkyl group, an aralkyl group, or an aryl group that may have a substituent. ]
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63111250A JPH01281453A (en) | 1988-05-07 | 1988-05-07 | Electrophotographic sensitive body |
| US07/345,236 US4920022A (en) | 1988-05-07 | 1989-05-01 | Electrophotographic photosensitive member comprising aryl amine charge transport material |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63111250A JPH01281453A (en) | 1988-05-07 | 1988-05-07 | Electrophotographic sensitive body |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01281453A JPH01281453A (en) | 1989-11-13 |
| JPH0454226B2 true JPH0454226B2 (en) | 1992-08-28 |
Family
ID=14556411
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63111250A Granted JPH01281453A (en) | 1988-05-07 | 1988-05-07 | Electrophotographic sensitive body |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01281453A (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2940502B2 (en) * | 1996-02-28 | 1999-08-25 | 日本電気株式会社 | Electrophotographic photoreceptor |
| JP4111406B2 (en) * | 1997-02-27 | 2008-07-02 | エルジー．フィリップス エルシーデー カンパニー，リミテッド | EL device and photoconductive imaging member |
| JP4153076B2 (en) * | 1998-03-05 | 2008-09-17 | 富士フイルム株式会社 | Aromatic tertiary amine compounds having benzazepine structure |
| CN102414176A (en) * | 2009-08-27 | 2012-04-11 | 三菱化学株式会社 | Monoamine compound, charge transport material, composition for charge transport film, organic electroluminescence element, organic EL display device, and organic EL lighting |
-
1988
- 1988-05-07 JP JP63111250A patent/JPH01281453A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH01281453A (en) | 1989-11-13 |
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