JP2009080233A - Electrophotographic photoreceptor - Google Patents
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Abstract
Description
本発明は、複写機、ファクシミリ、プリンタなどの画像形成装置に使用される電子写真感光体に関する。 The present invention relates to an electrophotographic photosensitive member used in an image forming apparatus such as a copying machine, a facsimile machine, and a printer.
上記の画像形成装置では、当該装置に用いられる光源の波長領域に感度を有する種々の感光体が使用されている。その１つはセレンなどの無機材料を感光層に用いた無機感光体であり、他は有機材料を感光層に用いた有機感光体である。有機感光体は、無機感光体に比べて製造が容易であり、かつ電荷発生剤、電荷輸送剤（電子輸送剤・正孔輸送剤）、バインダ樹脂などの材料選択肢が多様で、機能設計の自由度が高いことから、近年、多く使用されるようになっている。 In the image forming apparatus described above, various photoreceptors having sensitivity in the wavelength region of the light source used in the apparatus are used. One is an inorganic photoreceptor using an inorganic material such as selenium for the photosensitive layer, and the other is an organic photoreceptor using an organic material for the photosensitive layer. Organic photoconductors are easier to manufacture than inorganic photoconductors, and have a wide range of material options such as charge generators, charge transport agents (electron transport agents / hole transport agents), binder resins, etc. Due to its high degree, it has been used in recent years.
有機感光体には、電荷発生剤を含有した電荷発生層と電荷輸送剤を含有した電荷輸送層との積層構造からなる、いわゆる積層型感光体と、電荷発生剤と電荷輸送剤とを単一層に含有させた、いわゆる単層型感光体とがある。 The organic photoconductor includes a so-called laminated photoconductor comprising a charge generating layer containing a charge generating agent and a charge transporting layer containing a charge transporting agent, and a single layer comprising a charge generating agent and a charge transporting agent. And so-called single-layer type photoreceptors.
これらの有機感光体に電荷輸送剤として含有される電子輸送剤には、一般に、３，５−ジメチル−３’，５’−ジｔ−ブチルジフェノキノンが使用される。しかしながら、この電子輸送剤を含有した感光体では十分な感度が得られない。 Generally, 3,5-dimethyl-3 ', 5'-di-t-butyldiphenoquinone is used as the electron transporting agent contained as a charge transporting agent in these organic photoreceptors. However, sufficient sensitivity cannot be obtained with a photoreceptor containing this electron transport agent.
一方、特許文献１には電子写真感光体の残留電位を低くして、光感度を向上させることができ、特に単層型の感光体として好適に使用できる化合物として、フェニルベンゾジフラノン誘導体が開示されている。しかしながら、フェニルベンゾジフラノン誘導体を使用した電子写真感光体は、いまだ光感度が不十分であるという問題があった。
本発明の課題は、高い感度を有する電子写真感光体を提供することである。 An object of the present invention is to provide an electrophotographic photoreceptor having high sensitivity.
本発明者らは、上記課題を解決すべく鋭意研究を重ねた結果、下記一般式（１）で示す特定の構造を有するイソキノリノン誘導体を電子輸送剤として使用することにより、電子写真感光体の感度を向上させることができるという新たな事実を見出し、本発明を完成するに至った。 As a result of intensive studies to solve the above-mentioned problems, the present inventors have used an isoquinolinone derivative having a specific structure represented by the following general formula (1) as an electron transport agent, whereby the sensitivity of the electrophotographic photosensitive member is improved. As a result, the present inventors have found a new fact that it can be improved.
すなわち、本発明における電子写真感光体は、導電性基体上に、少なくとも電子輸送剤、電荷発生剤およびバインダ樹脂を含有した感光層が設けられたものであって、前記電子輸送剤が、下記一般式（１）で表される化合物であることを特徴とする。 That is, the electrophotographic photosensitive member in the present invention is obtained by providing a photosensitive layer containing at least an electron transport agent, a charge generating agent and a binder resin on a conductive substrate. It is a compound represented by Formula (1), It is characterized by the above-mentioned.
［式中、Ｒは、炭素数１〜６のアルキル基、炭素数１〜６のアルコキシ基、炭素数６〜２０のアラルキル基、炭素数６〜２０のアリール基、または、炭素数３〜１０のシクロアルキル基を示す。］ [Wherein, R represents an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an aralkyl group having 6 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, or 3 to 10 carbon atoms. The cycloalkyl group of is shown. ]
本発明の電子写真感光体は、バインダ樹脂等との相溶性に優れ且つ高い電荷移動度を示す前記一般式（１）で表される化合物を電子輸送剤として使用するので、残留電位を効果的に低下させ、高い感度を得ることができると共に、良好な画像が得られるという効果がある。 The electrophotographic photoreceptor of the present invention uses the compound represented by the general formula (1), which is excellent in compatibility with a binder resin and the like and exhibits high charge mobility, as an electron transport agent, so that the residual potential is effectively reduced. In addition to being able to obtain high sensitivity, a good image can be obtained.
本発明の電子写真感光体は、導電性基体上に、少なくとも電子輸送剤、電荷発生剤およびバインダ樹脂を含有し、さらに必要に応じて正孔輸送剤を含有した感光層を設けたものである。この感光層には、単層型感光層と積層型感光層とがあるが、本発明には、いずれの感光層も適用可能である。
＜電子輸送剤＞
本発明において使用する電子輸送剤は、前記一般式（１）で表される化合物である。この化合物は、溶解性が高いので、バインダ樹脂等との相溶性に優れると共に、長い共役結合を有しているので、高い電荷移動度を示す。
Ｒにおけるアルキル基としては、例えばメチル、エチル、ｎ−プロピル、イソプロピル、ｎ−ブチル、イソブチル、ｓ−ブチル、ｔ−ブチル、ペンチル、イソペンチル、ネオペンチル、ヘキシルなどの炭素数１〜６のアルキル基が挙げられる。また、アルコキシ基としては、例えばメトキシ、エトキシ、ｎ−プロポキシ、イソプロポキシ、ｎ−ブトキシ、ｓ−ブトキシ、ｔ−ブトキシ、ペンチルオキシ、イソペンチルオキシ、ネオペンチルオキシ、ヘキシルオキシ等が挙げられる。
Ｒにおけるアルコキシ基としては、例えばメトキシ、エトキシ、ｎ−プロポキシ、イソプロポキシ、ｎ−ブトキシ、ｓ−ブトキシ、ｔ−ブトキシ、ペンチルオキシ、イソペンチルオキシ、ネオペンチルオキシ、ヘキシルオキシ等が挙げられる。
Ｒにおけるアラルキル基としては、例えばベンジル、α−メチルベンジル、フェネチル、スチリル、シンナミル、３−フェニルプロピル、４−フェニルブチル、５−フェニルペンチル、６−フェニルヘキシル基などが挙げられる。
Ｒにおけるアリール基としては、例えばフェニル、ナフチル、トリル、キシリル、アントリル、フェナントリル等など炭素数６〜２０のアリール基が挙げられる。前記アリール基は１〜３個の置換基を有していてもよく、置換基として、炭素数１〜６のアルキル基、炭素数１〜６のアルコキシ基などが挙げられる。
Ｒにおけるシクロアルキル基としては、例えばシクロプロピル、シクロブチル、シクロペンチル、シクロヘキシル、シクロヘプチル、シクロオクチル等が挙げられる。
一般式（１）中、炭素数１〜６のアルキル基、炭素数１〜６のアルコキシ基、炭素数６〜２０のアラルキル基、炭素数６〜２０のアリール基、または、炭素数３〜１０のシクロアルキル基は置換基を有していてもよく、置換基としては、アルキル基、アルコキシ基、ハロゲン基、カルボキシ基、エステル基、アシル基、アミノ基、アルキルアミノ基、ニトロ基、メルカプト基、アリール基などが挙げられる。
The electrophotographic photosensitive member of the present invention is obtained by providing, on a conductive substrate, a photosensitive layer containing at least an electron transporting agent, a charge generating agent and a binder resin, and further containing a hole transporting agent as necessary. . The photosensitive layer includes a single-layer type photosensitive layer and a laminated type photosensitive layer, and any photosensitive layer can be applied to the present invention.
<Electron transport agent>
The electron transport agent used in the present invention is a compound represented by the general formula (1). Since this compound has high solubility, it has excellent compatibility with a binder resin and the like, and has a long conjugated bond, and thus exhibits high charge mobility.
Examples of the alkyl group for R include alkyl groups having 1 to 6 carbon atoms such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, pentyl, isopentyl, neopentyl, hexyl and the like. Can be mentioned. Examples of the alkoxy group include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, s-butoxy, t-butoxy, pentyloxy, isopentyloxy, neopentyloxy, hexyloxy and the like.
Examples of the alkoxy group for R include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, s-butoxy, t-butoxy, pentyloxy, isopentyloxy, neopentyloxy, hexyloxy and the like.
Examples of the aralkyl group in R include benzyl, α-methylbenzyl, phenethyl, styryl, cinnamyl, 3-phenylpropyl, 4-phenylbutyl, 5-phenylpentyl, 6-phenylhexyl group and the like.
Examples of the aryl group for R include aryl groups having 6 to 20 carbon atoms such as phenyl, naphthyl, tolyl, xylyl, anthryl, phenanthryl and the like. The aryl group may have 1 to 3 substituents, and examples of the substituent include an alkyl group having 1 to 6 carbon atoms and an alkoxy group having 1 to 6 carbon atoms.
Examples of the cycloalkyl group in R include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl and the like.
In general formula (1), a C1-C6 alkyl group, a C1-C6 alkoxy group, a C6-C20 aralkyl group, a C6-C20 aryl group, or C3-C10 The cycloalkyl group may have a substituent, and examples of the substituent include an alkyl group, an alkoxy group, a halogen group, a carboxy group, an ester group, an acyl group, an amino group, an alkylamino group, a nitro group, and a mercapto group. And aryl groups.
一般式（１）の合成方法を、下記化学反応式（１）に基づいて説明する。 A synthesis method of the general formula (1) will be described based on the following chemical reaction formula (1).
化合物（Ａ）の塩化メチレン溶液に、酢酸クロライト゛を加えて攪拌し、化合物（Ａ）の塩（Ａ´）を形成する。次いでそこにトリフルオロメタンスルホン酸を滴下し、室温で１〜５時間撹拌する。 Chlorite acetate is added to a methylene chloride solution of the compound (A) and stirred to form a salt (A ′) of the compound (A). Subsequently, trifluoromethanesulfonic acid is dripped there and it stirs at room temperature for 1 to 5 hours.
反応後、有機層から得られた残渣をカラムクロマトグラフィーで精製することで化合物（１）を得ることができる。 After the reaction, the compound (1) can be obtained by purifying the residue obtained from the organic layer by column chromatography.
（式中、Ｒは上記と同様である。）
本発明では、上記一般式（１）で表される化合物に加えて、公知の他の電子輸送剤を併用することもできる。これら他の電子輸送剤としては、例えばジフェノキノン誘導体、ベンゾキノン誘導体、ナフトキノン誘導体、アントラキノン誘導体、マロノニトリル誘導体、チオピラン誘導体、チオキサントン誘導体（２,４,８−トリニトロチオキサントン等）、フルオレノン誘導体（３,４,５,７−テトラニトロ−９−フルオレノン誘導体等）、アントラセン誘導体、アクリジン誘導体、ジニトロベンゼン、ジニトロアントラセン、ジニトロアクリジン、無水コハク酸誘導体、無水マレイン酸誘導体、ジブロモ無水マレイン酸誘導体等の、電子受容性を有する化合物が挙げられる。
＜電荷発生剤＞
前記電荷発生剤としては、例えば無金属フタロシアニン、ヒドロキシガリウムフタロシアニン、クロロガリウムフタロシアニン、α−チタニルフタロシアニン、Ｙ−チタニルフタロシアニン、Ｖ−ヒドロキシガリウムフタロシアニンなどのフタロシアニン系顔料、ペリレン系顔料、ビスアゾ顔料、ジオケトピロロピロール顔料、無金属ナフタロシアニン顔料、金属ナフタロシアニン顔料、スクアライン顔料、トリスアゾ顔料、インジゴ顔料、アズレニウム顔料、シアニン顔料、ピリリウム顔料、アンサンスロン顔料、トリフェニルメタン系顔料、スレン顔料、トルイジン系顔料、ピラゾリン系顔料、キナクリドン系顔料といった有機光導電体、セレン、セレン−テルル、セレン−ヒ素、硫化カドミニウム、アモルファスシリコンといった無機光導電材料などが挙げられる。中でも無金属フタロシアニン、クロロガリウムフタロシアニン、α−チタニルフタロシアニン、Ｙ−チタニルフタロシアニン、Ｖ−ヒドロキシガリウムフタロシアニンが好ましい。これらの電荷発生剤は単独でまたは２種以上をブレンドして用いてもよい。
＜バインダ樹脂＞
前記バインダ樹脂としては、例えばスチレン系重合体、スチレン−ブタジエン共重合体、スチレン−アクリロニトリル共重合体、スチレン−マレイン酸共重合体、アクリル系重合体、スチレン−アクリル系共重合体、ポリエチレン、エチレン−酢酸ビニル共重合体、塩素化ポリエチレン、ポリ塩化ビニル、ポリプロピレン、塩化ビニル−酢酸ビニル共重合体、ポリエステル、ポリアミド、ポリカーボネート、ポリアリレート、ポリスルホン、ジアリルフタレート樹脂、ケトン樹脂、ポリビニルブチラール樹脂、ポリエーテル樹脂等の熱可塑性樹脂や、シリコーン樹脂、エポキシ樹脂、フェノール樹脂、尿素樹脂、メラミン樹脂、不飽和ポリエステル、アルキッド樹脂、ポリウレタン、その他架橋性の熱硬化性樹脂、さらにエポキシ−アクリレート、ウレタン−アクリレート等の光硬化性樹脂等が挙げられる。これらはそれぞれ単独で使用できるほか、２種以上をブレンドすることもできる。
＜正孔輸送剤＞
さらに、本発明では正孔輸送剤を感光層に含有させてもよい。特に単層型感光体では、感光層中に正孔輸送剤および電子輸送剤が含有される。前記正孔輸送剤としては、例えばＮ，Ｎ，Ｎ’，Ｎ’−テトラフェニルベンジジン誘導体、Ｎ，Ｎ，Ｎ’，Ｎ’−テトラフェニルフェニレンジアミン誘導体、Ｎ，Ｎ，Ｎ’，Ｎ’−テトラフェニルナフチレンジアミン誘導体、Ｎ，Ｎ，Ｎ’，Ｎ’−テトラフェニルフェナントリレンジアミン誘導体、２，５−ジ（４−メチルアミノフェニル）−１，３，４−オキサジアゾールなどのオキサジアゾール系化合物、９−（４−ジエチルアミノスチリル）アントラセンなどのスチリル系化合物、ポリビニルカルバゾールなどのカルバゾール系化合物、有機ポリシラン化合物、１−フェニル−３−（ｐ−ジメチルアミノフェニル）ピラゾリンなどのピラゾリン系化合物、ヒドラゾン系化合物、インドール系化合物、オキサゾール系化合物、イソオキサゾール系化合物、チアゾール系化合物、チアジゾール系化合物、イミダゾール系化合物、ピラゾール系化合物、トリアゾール系化合物等の含窒素環式化合物や、縮合多環式化合物が挙げられる。
＜感光層＞
（単層型）
本発明における単層型感光層は、上記した電子輸送剤、電荷発生剤、バインダ樹脂を同一層に含有した単一の感光層で構成されるものである。この単層型感光層は、層構成が簡単で生産性に優れており、層を形成する際の被膜欠陥を抑制でき、層間の界面が少なく光学的特性を向上できるという利点がある。なお、電荷輸送剤には電子輸送剤と正孔輸送剤とがあり、上記したように、特に単層型感光体においては、電子輸送剤と正孔輸送剤とを併用するのが好ましい。
(In the formula, R is the same as above.)
In the present invention, in addition to the compound represented by the general formula (1), other known electron transport agents can be used in combination. Examples of these other electron transporting agents include diphenoquinone derivatives, benzoquinone derivatives, naphthoquinone derivatives, anthraquinone derivatives, malononitrile derivatives, thiopyran derivatives, thioxanthone derivatives (2,4,8-trinitrothioxanthone, etc.), fluorenone derivatives (3,4,4, etc.). 5,7-tetranitro-9-fluorenone derivatives), anthracene derivatives, acridine derivatives, dinitrobenzene, dinitroanthracene, dinitroacridine, succinic anhydride derivatives, maleic anhydride derivatives, dibromomaleic anhydride derivatives, etc. The compound which has is mentioned.
<Charge generator>
Examples of the charge generator include phthalocyanine pigments such as metal-free phthalocyanine, hydroxygallium phthalocyanine, chlorogallium phthalocyanine, α-titanyl phthalocyanine, Y-titanyl phthalocyanine, and V-hydroxygallium phthalocyanine, perylene pigments, bisazo pigments, diketo Pyrrolopyrrole pigment, metal-free naphthalocyanine pigment, metal naphthalocyanine pigment, squaraine pigment, trisazo pigment, indigo pigment, azulenium pigment, cyanine pigment, pyrylium pigment, ansanthrone pigment, triphenylmethane pigment, selenium pigment, toluidine pigment , Organic photoconductors such as pyrazoline pigments and quinacridone pigments, inorganic materials such as selenium, selenium-tellurium, selenium-arsenic, cadmium sulfide, and amorphous silicon Such as a conductive material. Of these, metal-free phthalocyanine, chlorogallium phthalocyanine, α-titanyl phthalocyanine, Y-titanyl phthalocyanine, and V-hydroxygallium phthalocyanine are preferable. These charge generating agents may be used alone or in combination of two or more.
<Binder resin>
Examples of the binder resin include a styrene polymer, a styrene-butadiene copolymer, a styrene-acrylonitrile copolymer, a styrene-maleic acid copolymer, an acrylic polymer, a styrene-acrylic copolymer, polyethylene, and ethylene. -Vinyl acetate copolymer, chlorinated polyethylene, polyvinyl chloride, polypropylene, vinyl chloride-vinyl acetate copolymer, polyester, polyamide, polycarbonate, polyarylate, polysulfone, diallyl phthalate resin, ketone resin, polyvinyl butyral resin, polyether Thermoplastic resins such as resins, silicone resins, epoxy resins, phenol resins, urea resins, melamine resins, unsaturated polyesters, alkyd resins, polyurethanes, other crosslinkable thermosetting resins, and epoxy-acrylic resins. DOO, urethane - photocurable resin such as acrylate. These can be used alone or in combination of two or more.
<Hole transport agent>
Furthermore, in the present invention, a hole transport agent may be contained in the photosensitive layer. In particular, in a single layer type photoreceptor, a hole transport agent and an electron transport agent are contained in the photosensitive layer. Examples of the hole transport agent include N, N, N ′, N′-tetraphenylbenzidine derivatives, N, N, N ′, N′-tetraphenylphenylenediamine derivatives, N, N, N ′, N′— Tetraphenylnaphthylene diamine derivatives, N, N, N ′, N′-tetraphenylphenanthrylenediamine derivatives, oxa such as 2,5-di (4-methylaminophenyl) -1,3,4-oxadiazole Pyrazoline compounds such as diazole compounds, styryl compounds such as 9- (4-diethylaminostyryl) anthracene, carbazole compounds such as polyvinyl carbazole, organic polysilane compounds, 1-phenyl-3- (p-dimethylaminophenyl) pyrazoline Compounds, hydrazone compounds, indole compounds, oxazole compounds, isoxazole compounds Things, thiazole compounds, Chiajizoru compounds, imidazole compounds, pyrazole compounds, and nitrogen-containing cyclic compounds such as triazole compounds, and condensed polycyclic compounds.
<Photosensitive layer>
(Single layer type)
The single-layer type photosensitive layer in the present invention is composed of a single photosensitive layer containing the above-described electron transport agent, charge generating agent, and binder resin in the same layer. This single-layer type photosensitive layer has an advantage that it has a simple layer structure and is excellent in productivity, can suppress film defects when forming the layer, and can improve optical characteristics with few interfaces between layers. The charge transport agent includes an electron transport agent and a hole transport agent, and as described above, it is preferable to use the electron transport agent and the hole transport agent in combination, particularly in a single layer type photoreceptor.
前記単層型感光層の膜厚は５〜１００μｍ、好ましくは１０〜５０μｍである。単層型感光層においては、バインダ樹脂１００質量部に対して電荷発生剤を０．１〜５０質量部、好ましくは０．５〜３０質量部の割合で、電子輸送剤を５〜１００質量部、好ましくは１０〜８０質量部の割合でそれぞれ含有させるのがよい。また、正孔輸送剤を含有させる場合は、バインダ樹脂１００質量部に対して５〜５００質量部、好ましくは２５〜２００質量部の割合で含有させるのがよい。
（積層型）
一方、積層型感光層は、導電性基体上に電荷輸送剤を含有する電荷輸送層と、電荷発生剤を含有する電荷発生層とを積層することで構成される。また、電荷発生剤と共に電荷輸送剤を含有させた光導電層を、電荷輸送層、電荷発生層と組み合わせてもよい。積層型感光層は、上記電荷発生層、電荷輸送層などの形成順序と、両層に含有させる電荷輸送剤の種類（電子輸送剤・正孔輸送剤）によって種々の組み合わせが考えられるが、本発明においては、電荷輸送層および光導電層の少なくとも1つに、電子輸送剤として一般式（１）で表される化合物を含有させる必要がある。なお、積層型感光体は、電荷発生や電荷輸送といった機能を各層に分離しているので、構成材料の無駄が少なく、感度を向上させ易いという利点を有する。
The film thickness of the single layer type photosensitive layer is 5 to 100 μm, preferably 10 to 50 μm. In the single-layer type photosensitive layer, the charge generating agent is 0.1 to 50 parts by weight, preferably 0.5 to 30 parts by weight, and the electron transport agent is 5 to 100 parts by weight with respect to 100 parts by weight of the binder resin. , Preferably 10 to 80 parts by mass, respectively. Moreover, when it contains a hole transport agent, it is good to make it contain in the ratio of 5-500 mass parts with respect to 100 mass parts of binder resin, Preferably it is 25-200 mass parts.
(Laminated type)
On the other hand, the laminated photosensitive layer is constituted by laminating a charge transport layer containing a charge transport agent and a charge generation layer containing a charge generator on a conductive substrate. Further, a photoconductive layer containing a charge transporting agent together with a charge generating agent may be combined with a charge transporting layer and a charge generating layer. There are various combinations of the layered photosensitive layer depending on the order of formation of the charge generation layer, the charge transport layer, etc., and the type of the charge transport agent (electron transport agent / hole transport agent) contained in both layers. In the invention, it is necessary that at least one of the charge transport layer and the photoconductive layer contains a compound represented by the general formula (1) as an electron transport agent. In addition, since the laminated photoconductor separates functions such as charge generation and charge transport in each layer, there is an advantage that constituent materials are not wasted and sensitivity is easily improved.
前記電荷発生層の膜厚は０．０１〜５μｍ、好ましくは０．１〜３μｍであり、電荷輸送層の膜厚は２〜１００μｍ、好ましくは５〜５０μｍである。積層型感光層のうち電荷発生層においては、バインダ樹脂１００質量部に対して電荷発生剤を５〜１０００質量部、好ましくは３０〜５００質量部の割合で含有させるのがよい。また、電荷輸送層においては、バインダ樹脂１００質量部に対して電子輸送剤を１〜２５０質量部、好ましくは５〜１５０質量部の割合で含有させるのがよい。また、電子輸送剤と正孔輸送剤を併用する場合は、その総量がバインダ樹脂１００質量部に対して１０〜５００質量部、好ましくは３０〜２００質量部の割合で含有させるのがよい。 The charge generation layer has a thickness of 0.01 to 5 μm, preferably 0.1 to 3 μm, and the charge transport layer has a thickness of 2 to 100 μm, preferably 5 to 50 μm. In the charge generating layer of the laminated photosensitive layer, the charge generating agent is preferably contained in an amount of 5 to 1000 parts by weight, preferably 30 to 500 parts by weight, based on 100 parts by weight of the binder resin. In the charge transport layer, the electron transport agent may be contained in an amount of 1 to 250 parts by mass, preferably 5 to 150 parts by mass with respect to 100 parts by mass of the binder resin. Moreover, when using together an electron transport agent and a hole transport agent, the total amount is 10-500 mass parts with respect to 100 mass parts of binder resin, Preferably it is good to make it contain in the ratio of 30-200 mass parts.
感光層には、前記した成分のほかに、画像形成に悪影響を与えない範囲で、種々の添加剤を配合することができる。このような添加剤としては、例えば酸化防止剤、ラジカル捕捉剤、一重項クエンチャー、紫外線吸収剤などの劣化防止剤、軟化剤、可塑剤、表面改質剤、増量剤、増粘剤、分散安定剤、ワックス、アクセプター、ドナーなどが挙げられる。また、感度を向上させるために、例えばテルフェニル、ハロナフトキノン類、アセナフチレン等の公知の増感剤を電荷発生剤と併用してもよい。
＜導電性基体＞
導電性基体としては、導電性を有する各種の材料が使用可能であり、例えば鉄、アルミニウム、銅、スズ、白金、銀、バナジウム、モリブデン、クロム、カドミウム、チタン、ニッケル、パラジウム、インジウム、ステンレス鋼、真鍮などの金属単体、上記金属が蒸着もしくはラミネートされたプラスチック材料、カーボンブラック等の導電性微粒子が分散されたプラスチック材料、さらにヨウ化アルミニウム、酸化スズ、酸化インジウムなどで被覆されたガラスなどが挙げられる。導電性基体と感光層との間には、感光体の特性を阻害しない範囲でバリア層が形成されていてもよい。また、感光層の表面には保護層が形成されていてもよい。
In addition to the components described above, various additives can be blended in the photosensitive layer within a range that does not adversely affect image formation. Examples of such additives include antioxidants, radical scavengers, singlet quenchers, deterioration inhibitors such as UV absorbers, softeners, plasticizers, surface modifiers, extenders, thickeners, dispersions. Stabilizers, waxes, acceptors, donors and the like can be mentioned. In order to improve sensitivity, for example, known sensitizers such as terphenyl, halonaphthoquinones, and acenaphthylene may be used in combination with the charge generator.
<Conductive substrate>
As the conductive substrate, various conductive materials can be used. For example, iron, aluminum, copper, tin, platinum, silver, vanadium, molybdenum, chromium, cadmium, titanium, nickel, palladium, indium, stainless steel Metal materials such as brass, plastic materials on which the above metals are deposited or laminated, plastic materials in which conductive fine particles such as carbon black are dispersed, and glass coated with aluminum iodide, tin oxide, indium oxide, etc. Can be mentioned. A barrier layer may be formed between the conductive substrate and the photosensitive layer as long as the characteristics of the photoreceptor are not impaired. A protective layer may be formed on the surface of the photosensitive layer.
導電性基体は、使用する画像形成装置の構造に合わせてドラム状、シート状などの形態で使用される。この導電性基体は充分な機械的強度を有しているのが好ましい。単層型の感光層を形成するには、電子輸送剤、電荷発生剤およびバインダ樹脂、さらに必要に応じて正孔輸送剤や他の添加剤を適当な溶媒と共に、ロールミル、ボールミル、アトライタ、ペイントシェーカー、超音波分散機などを用いて混合して分散液を調製し、この分散液を導電性基体上に公知の手段で塗布して乾燥させればよい。また、積層型感光体の電荷発生層および電荷輸送層を形成するには、電荷発生剤、電荷輸送剤を適当なバインダ樹脂および溶媒と共に上記と同一の方法で分散液を調製し、これを公知の手段により塗布して乾燥させればよい。 The conductive substrate is used in the form of a drum or a sheet according to the structure of the image forming apparatus to be used. The conductive substrate preferably has sufficient mechanical strength. In order to form a single-layer type photosensitive layer, an electron transport agent, a charge generator and a binder resin, and optionally a hole transport agent and other additives together with an appropriate solvent, a roll mill, a ball mill, an attritor, a paint What is necessary is just to prepare a dispersion by mixing using a shaker, an ultrasonic disperser, etc., apply this dispersion on a conductive substrate by a known means, and dry it. In order to form the charge generating layer and the charge transport layer of the multilayer photoreceptor, a dispersion is prepared by the same method as described above together with the charge generator and the charge transport agent together with an appropriate binder resin and solvent, and this is publicly known. What is necessary is just to apply | coat and dry by the means of.
前記分散液を調製するための溶媒としては、例えばメタノール、エタノール、イソプロパノール、ブタノールなどのアルコール類、ｎ−ヘキサン、オクタン、シクロヘキサンなどの脂肪族炭化水素、ベンゼン、トルエン、キシレンなどの芳香族炭化水素、ジクロロメタン、ジクロロエタン、四塩化炭素、クロロベンゼンなどのハロゲン化炭化水素、ジメチルエーテル、ジエチルエーテル、テトラヒドロフラン、エチレングリコールジメチルエーテル、ジエチレングリコールジメチルエーテル、ジオキサン、ジオキソランなどのエーテル類、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、酢酸エチル、酢酸メチルなどのエステル類、ジメチルホルムアルデヒド、ジメチルホルムアミド、ジメチルスルホキシドなどが挙げられる。これらの溶媒は単独で使用するほか、２種以上を混合して用いてもよい。さらに、電荷発生剤および電荷輸送剤の分散性、感光体表面の平滑性を良くするために、界面活性剤、レベリング剤などを使用してもよい。 Examples of the solvent for preparing the dispersion include alcohols such as methanol, ethanol, isopropanol and butanol, aliphatic hydrocarbons such as n-hexane, octane and cyclohexane, and aromatic hydrocarbons such as benzene, toluene and xylene. , Halogenated hydrocarbons such as dichloromethane, dichloroethane, carbon tetrachloride and chlorobenzene, ethers such as dimethyl ether, diethyl ether, tetrahydrofuran, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, dioxane and dioxolane, ketones such as acetone, methyl ethyl ketone and cyclohexanone, acetic acid Examples include esters such as ethyl and methyl acetate, dimethylformaldehyde, dimethylformamide, and dimethyl sulfoxide. That. These solvents may be used alone or in combination of two or more. Further, in order to improve the dispersibility of the charge generating agent and the charge transport agent and the smoothness of the surface of the photoreceptor, a surfactant, a leveling agent and the like may be used.
次に実施例および比較例を挙げて本発明の電子写真感光体を説明するが、本発明は以下の実施例のみに限定されるものではない。 Next, the electrophotographic photoreceptor of the present invention will be described with reference to examples and comparative examples, but the present invention is not limited to the following examples.
以下、実施例および比較例を挙げて本発明を詳細に説明する。 Hereinafter, the present invention will be described in detail with reference to Examples and Comparative Examples.
実施例で使用した電子輸送剤は、以下の３種類である。 The following three types of electron transport agents were used in the examples.
（合成例１）
化合物（１-１）の合成方法を、上記化学反応式（１-１）に基づいて説明する。
(Synthesis Example 1)
A synthesis method of the compound (1-1) will be described based on the chemical reaction formula (1-1).
化合物（Ａ−１）（０．３ｇ、１ｍｍｏｌ）の塩化メチレン溶液に、酢酸クロライド（０．０８ｇ、１ｍｍｏｌ）を加えて２時間撹拌した。次いでそこにトリフルオロメタンスルホン酸（０．９ｇ、６ｍｍｏｌ）を滴下し、室温で３時間撹拌した。反応後、反応液を氷水に注いでクロロホルムで抽出し、有機層を留去してから残渣をカラムクロマトグラフィーで精製し、化合物（１−１）を０．１９ｇ得た。収率６５％ Acetic acid chloride (0.08 g, 1 mmol) was added to a methylene chloride solution of compound (A-1) (0.3 g, 1 mmol) and stirred for 2 hours. Next, trifluoromethanesulfonic acid (0.9 g, 6 mmol) was added dropwise thereto, and the mixture was stirred at room temperature for 3 hours. After the reaction, the reaction solution was poured into ice water and extracted with chloroform, the organic layer was distilled off, and the residue was purified by column chromatography to obtain 0.19 g of compound (1-1). Yield 65%
（合成例２）
合成例１において化合物（Ａ−１）０．３ｇを下記化合物（Ａ−２）０．３５ｇに変えた以外は、合成例１と同様に行い、化合物（１−２）を０．２１ｇ得た。（収率６０％）
(Synthesis Example 2)
Except having changed 0.3g of compound (A-1) into 0.35g of the following compound (A-2) in the synthesis example 1, it carried out similarly to the synthesis example 1, and obtained 0.21g of compounds (1-2). . (Yield 60%)
（合成例３）
合成例１において化合物（Ａ−１）０．３ｇを下記化合物（Ａ−３）に変えた以外は、合成例１と同様に行い、化合物（１−３）を０．１９ｇ得た。（収率６２％）
(Synthesis Example 3)
Except having changed 0.3 g of compounds (A-1) into the following compound (A-3) in the synthesis example 1, it carried out similarly to the synthesis example 1, and obtained 0.19g of compounds (1-3). (Yield 62%)
比較例で使用した電子輸送剤、実施例および比較例で使用した電荷発生剤、バインダ樹脂および正孔輸送剤は以下の通りである。
＜比較例で使用した電子輸送剤＞
The electron transport agent used in the comparative examples, the charge generating agent, the binder resin and the hole transport agent used in the examples and comparative examples are as follows.
<Electron transport agent used in comparative example>
＜電荷発生剤＞ <Charge generator>
＜バインダ樹脂＞ <Binder resin>
＜正孔輸送剤＞ <Hole transport agent>
［実施例１〜６］
［比較例１〜２］
＜電子写真感光体の作製＞
上記の電子輸送剤、電荷発生剤、バインダ樹脂および正孔輸送剤を表１に示す組み合わせで用いた。すなわち、溶媒であるテトラヒドロフラン８００質量部に対して、バインダ樹脂（Ｒｅｓｉｎ−１：粘度平均分子量５０，０００のビスフェノールＺ型ポリカーボネート樹脂）１００重量部、正孔輸送剤（Ｈ−１）５０重量部、表１に示す電荷発生剤（Ｘ−Ｈ2ＰｃまたはＹ−ＴｉＯＰｃ）３重量部、および表１に示す電子輸送剤（１−１〜１−３、ＥＴ−１）５０重量部を添加した。この混合物を超音波分散機で１時間混合分散して、単層型感光層用の分散液を作製した。ついで、得られた分散液を導電性基材（アルミニウム素管）上にディップコート法にて塗布し、１００℃で３０分間で熱風乾燥して、膜厚３０μｍの単層型感光層を有する電子写真感光体を得た。
[Examples 1 to 6]
[Comparative Examples 1-2]
<Production of electrophotographic photoreceptor>
The combinations shown in Table 1 were used for the electron transport agent, charge generator, binder resin, and hole transport agent. That is, 100 parts by weight of a binder resin (Resin-1: bisphenol Z-type polycarbonate resin having a viscosity average molecular weight of 50,000), 50 parts by weight of a hole transporting agent (H-1) with respect to 800 parts by weight of tetrahydrofuran as a solvent. 3 parts by weight of a charge generator (X—H 2 Pc or Y—TiOPc) shown in Table 1 and 50 parts by weight of an electron transport agent (1-1 to 1-3, ET-1) shown in Table 1 were added. This mixture was mixed and dispersed with an ultrasonic disperser for 1 hour to prepare a dispersion for a single-layer type photosensitive layer. Next, the obtained dispersion is applied on a conductive substrate (aluminum tube) by dip coating, dried with hot air at 100 ° C. for 30 minutes, and an electron having a single-layer type photosensitive layer having a thickness of 30 μm. A photographic photoreceptor was obtained.
次に、上記で得られた電子写真感光体の感度特性を以下のようにして評価した。すなわち、電子写真感光体について、ドラム感度試験機（ＧＥＮＴＥＣ社製）を用いて、７００Ｖになるように帯電させ、ついでハロゲンランプの光からバンドパスフィルターを用いて取り出した波長７８０ｎｍの単色光（半値幅：２０ｎｍ、光量：１．５μＪ／ｃｍ2）を露光［照射時間：０．０８秒（８０ｍｓｅｃ）］した。そして、露光開始から０．３３秒（３３０ｍｓｅｃ）経過した時点での表面電位（残留電位）を測定し、それを感度とした。結果を表１に示す。 Next, the sensitivity characteristics of the electrophotographic photosensitive member obtained above were evaluated as follows. That is, the electrophotographic photosensitive member is charged to 700 V using a drum sensitivity tester (manufactured by GENTEC), and then monochromatic light having a wavelength of 780 nm extracted from the light of the halogen lamp using a bandpass filter (half-color) Value width: 20 nm, light quantity: 1.5 μJ / cm 2 ) was exposed [irradiation time: 0.08 seconds (80 msec)]. Then, the surface potential (residual potential) at the time when 0.33 seconds (330 msec) had elapsed from the start of exposure was measured and used as sensitivity. The results are shown in Table 1.
表１から、電子輸送剤として、一般式（１）で表される化合物を用いた実施例１〜４の電子写真感光体は、比較例の電子写真感光体に比べて高い感度を有していることがわかる。 From Table 1, the electrophotographic photoreceptors of Examples 1 to 4 using the compound represented by the general formula (1) as the electron transport agent have higher sensitivity than the electrophotographic photoreceptor of the comparative example. I understand that.
Claims (1)
前記電子輸送剤が、下記一般式（１）で表される化合物であることを特徴とする電子写真感光体。
［式中、Ｒは、炭素数１〜６のアルキル基、炭素数１〜６のアルコキシ基、炭素数６〜２０のアラルキル基、炭素数６〜２０のアリール基、または、炭素数３〜１０のシクロアルキル基を示す。］ An electrophotographic photosensitive member in which a photosensitive layer containing at least an electron transport agent, a charge generator and a binder resin is provided on a conductive substrate,
The electrophotographic photoreceptor, wherein the electron transfer agent is a compound represented by the following general formula (1).
[Wherein, R represents an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an aralkyl group having 6 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, or 3 to 10 carbon atoms. The cycloalkyl group of is shown. ]
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