JP3496085B2 - Electrophotographic photoreceptor - Google Patents
Electrophotographic photoreceptorInfo
- Publication number
- JP3496085B2 JP3496085B2 JP26802796A JP26802796A JP3496085B2 JP 3496085 B2 JP3496085 B2 JP 3496085B2 JP 26802796 A JP26802796 A JP 26802796A JP 26802796 A JP26802796 A JP 26802796A JP 3496085 B2 JP3496085 B2 JP 3496085B2
- Authority
- JP
- Japan
- Prior art keywords
- layer
- general formula
- coating solution
- charge transport
- charge
- 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 - Fee Related
Links
Landscapes
- Photoreceptors In Electrophotography (AREA)
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、電子写真感光体に
関し、詳しくは、特定の電荷輸送材料を使用した、光感
度、印字特性、繰り返し使用特性に優れた電子写真感光
体に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an electrophotographic photosensitive member, and more particularly to an electrophotographic photosensitive member which uses a specific charge transporting material and is excellent in photosensitivity, printing characteristics and repeated use characteristics.
【０００２】[0002]
【従来の技術】有機系の電子写真感光体において、その
感度を高めるために電荷発生層と電荷輸送層を積層した
機能分離型と呼ばれる感光体が注目され実用化されてい
る。この機能分離型の感光体における静電潜像形成のメ
カニズムは、感光体を帯電した後、光照射すると、光は
電荷発生層により吸収され、光を吸収した電荷発生層は
電荷担体を発生し、この電荷担体は電荷輸送層に注入さ
れ、帯電によって生じている電界にしたがって電荷輸送
層（ないしは感光層）中を移動し、感光体表面の電荷を
中和することにより静電潜像を形成するものである。2. Description of the Related Art In an organic electrophotographic photosensitive member, a photosensitive member called a function separation type, in which a charge generating layer and a charge transporting layer are laminated in order to enhance its sensitivity, has been attracting attention and put to practical use. The mechanism of electrostatic latent image formation in this function-separated type photoconductor is that when the photoconductor is charged and then irradiated with light, the light is absorbed by the charge generation layer, and the charge generation layer absorbing the light generates charge carriers. , The charge carriers are injected into the charge transport layer, move in the charge transport layer (or photosensitive layer) according to the electric field generated by charging, and form an electrostatic latent image by neutralizing the charge on the surface of the photoreceptor. To do.
【０００３】従来から、種々の感光体材料が開発されて
いるが、これらを実用化できる優れた電子写真感光体に
するには、感度、受容電位、電位保持性、電位安定性、
残留電位、分光特性に代表される電子写真特性、耐摩耗
性等の機械的耐久性、熱、光、放電生成物等に対する化
学的安定性等、種々の特性が要求される。とりわけ、高
感度で繰り返し安定性に優れたものであることが重要で
あるが、上述したようにある程度の高感度特性は、適切
な電荷発生材料と電荷輸送材料の組合せにより達成する
ことが可能である。一方、これに加えて機械的耐久性を
合わせ持つことについての検討もなされているが、従来
から提案されている電荷発生材料と電荷輸送材料との組
合せによっては上記条件の全てを満たすものは得られて
いなかった。従って、従来から提案されている電荷発生
材料と電荷輸送材料を使用して、高感度を維持し、か
つ、繰り返し使用による安定性に優れた電子写真感光体
の完成が熱望されていた。Conventionally, various photoconductor materials have been developed, but in order to make them excellent electrophotographic photoconductors that can be put to practical use, sensitivity, receptive potential, potential holding property, potential stability,
Various characteristics such as residual potential, electrophotographic characteristics represented by spectral characteristics, mechanical durability such as abrasion resistance, chemical stability against heat, light, discharge products, etc. are required. In particular, it is important that the material has high sensitivity and excellent repeatability stability, but as described above, some high sensitivity characteristics can be achieved by a combination of an appropriate charge generation material and charge transport material. is there. On the other hand, in addition to this, studies have also been made to have mechanical durability, but depending on the combination of the charge generating material and the charge transporting material that have been conventionally proposed, it is not possible to satisfy all of the above conditions. It wasn't done. Therefore, it has been earnestly desired to complete an electrophotographic photosensitive member which maintains high sensitivity and is excellent in stability by repeated use, using the charge generating material and the charge transporting material which have been conventionally proposed.
【０００４】[0004]
【発明が解決しようとする課題】本発明の課題は、高感
度を失うことなく繰り返し使用によっても優れた安定性
を示す電子写真感光体を提供することである。SUMMARY OF THE INVENTION An object of the present invention is to provide an electrophotographic photosensitive member which exhibits excellent stability even after repeated use without losing high sensitivity.
【０００５】[0005]
【課題を解決するための手段】本発明によれば、第一
に、導電性支持体上に電荷発生材料を主成分とする電荷
発生層と少なくとも下記（２）、（４）ないし（８）で
示される化合物の組から選択される一組を含有する電荷
輸送層を積層してなることを特徴とする電子写真感光体
が提供される。
（２）一般式（Ｉ）で示される化合物と一般式（ＩＩ
Ｉ）で示される化合物
（４）一般式（Ｉ）で示される化合物と一般式（Ｖ）で
示される化合物
（５）一般式（Ｉ）で示される化合物と一般式（ＶＩ）
で示される化合物
（６）一般式（Ｉ）で示される化合物と一般式（ＶＩ
Ｉ）で示される化合物
（７）一般式（Ｉ）で示される化合物と一般式（ＶＩＩ
Ｉ）で示される化合物
（８）一般式（Ｉ）で示される化合物と一般式（ＩＸ）
で示される化合物第三に
、導電性支持体上に少なくとも電荷発生材料と下
記（２）、（４）ないし（８）で示される化合物の組か
ら選択される一組を含有する単層感光層を設けてなるこ
とを特徴とする電子写真感光体が提供される。
（２）一般式（Ｉ）で示される化合物と一般式（ＩＩ
Ｉ）で示される化合物
（４）一般式（Ｉ）で示される化合物と一般式Ｖで示さ
れる化合物
（５）一般式（Ｉ）で示される化合物と一般式（ＶＩ）
で示される化合物
（６）一般式（Ｉ）で示される化合物と一般式（ＶＩ
Ｉ）で示される化合物
（７）一般式（Ｉ）で示される化合物と一般式（ＶＩＩ
Ｉ）で示される化合物
（８）一般式（Ｉ）で示される化合物と一般式（ＩＸ）
で示される化合物According to the present invention, the first
And a charge transporting layer containing a charge generating layer containing a charge generating material as a main component and at least one set selected from the set of compounds represented by the following (2), (4) to (8) on a conductive support. Provided is an electrophotographic photosensitive member characterized by being formed by laminating layers. (2) The compound represented by the general formula (I) and the general formula (II
I) compound (4) compound represented by general formula (I) and compound (5) represented by general formula (V) compound represented by general formula (I) and general formula (VI)
The compound (6) represented by the formula (VI) and the compound represented by the general formula (VI)
Compound (7) represented by general formula (I) and compound represented by general formula (VII)
Compound (8) represented by I) and compound represented by the general formula (IX)
Thirdly, a single-layer photosensitive layer containing at least a charge generating material and one set selected from the set of compounds shown in the following (2), (4) to (8) on a conductive support. An electrophotographic photoreceptor is provided which is provided with. (2) The compound represented by the general formula (I) and the general formula ( II
Compounds represented by I) (4) General formula (I) compound with a compound represented by the general formula V represented by (5) a compound represented by the general formula (I) and formula (V I)
Compound (6) represented by the general formula ( VI)
Compounds represented by I) (7) a compound represented by the general formula (I) and formula (VII
Compounds represented by I) (8) a compound represented by the general formula (I) and the general formula (IX)
Compound shown by
【０００６】以下に本発明を詳細に説明する。本発明者
らは上記課題に関して検討を重ねた結果、感光層に上記
特定の組合せの電荷輸送材料を用いることにより、繰り
返し使用によっても画質欠陥の発生が抑制され、しかも
優れた電子写真特性をあわせもつ電子写真感光体が得ら
れることを見出し、本発明に至った。The present invention will be described in detail below. As a result of repeated studies on the above-mentioned problems, the inventors of the present invention suppress the occurrence of image quality defects even after repeated use by using the charge-transporting material in the above-mentioned specific combination in the photosensitive layer, and combine excellent electrophotographic characteristics. It was found that an electrophotographic photoreceptor having the above can be obtained, and the present invention was completed.
【０００７】図面を用いて、本発明の電子写真感光体を
説明すると、図１は、本発明における単層感光体を表わ
す断面図であり、導電性支持体１１上に、感光層１５が
設けられている。図２、図３は、本発明における積層感
光体の構成例を示す断面図であり、電荷発生材料を主成
分とする電荷発生層１７と、電荷輸送材料を主成分とす
る電荷輸送層１９とが、積層された構成をとっている。
このような単層、または積層感光体において、上述した
一般式（Ｉ）示される化合物と一般式（ＩＩ）ないし
（ＩＸ）でそれぞれ示される化合物から選択された少な
くとも１種とからなる電荷輸送材料が併用して用いられ
る。The electrophotographic photosensitive member of the present invention will be described with reference to the drawings. FIG. 1 is a sectional view showing a single-layer photosensitive member of the present invention. A photosensitive layer 15 is provided on a conductive support 11. Has been. FIG. 2 and FIG. 3 are cross-sectional views showing an example of the structure of the laminated photoreceptor according to the present invention. The charge generation layer 17 contains a charge generation material as a main component, and the charge transport layer 19 contains a charge transport material as a main component. However, it has a laminated structure.
In such a single-layer or laminated photoreceptor, a charge transport material comprising the compound represented by the general formula (I) and at least one selected from the compounds represented by the general formulas (II) to (IX). Are used in combination.
【０００８】[0008]
【発明の実施の形態】以下に発明の実施の形態について
述べる。導電性支持体１１としては、体積抵抗１０１０
Ωｃｍ以下の導電性を示すもの、例えば、アルミニウ
ム、ニッケル、クロム、ニクロム、銅、銀、金、白金な
どの金属、酸化スズ、酸化インジウムなどの金属酸化物
を、蒸着またはスパッタリングにより、フィルム状もし
くは円筒状のプラスチックもしくは紙に被覆したもの、
あるいは、アルミニウム、アルミニウム合金、ニッケ
ル、ステンレス等の板およびそれらを素管化後、切削、
超仕上げ、研磨等で表面処理した管等を使用することが
できる。BEST MODE FOR CARRYING OUT THE INVENTION Embodiments of the present invention will be described below. The conductive support 11 has a volume resistance of 10 10.
Those exhibiting conductivity of Ωcm or less, for example, a metal such as aluminum, nickel, chromium, nichrome, copper, silver, gold, platinum, or a metal oxide such as tin oxide or indium oxide by vapor deposition or sputtering into a film or Cylindrical plastic or paper coated,
Alternatively, aluminum, aluminum alloy, nickel, stainless steel plates and the like, after cutting them into a tube, cutting,
It is possible to use a tube or the like which has been surface-treated by superfinishing, polishing or the like.
【０００９】次に感光層１５について説明する。説明の
都合上、先ず電荷発生層１７と電荷輸送層１９が積層さ
れた構成の場合から述べる。電荷発生層１７は、電荷発
生材料を主成分とする層である。電荷発生材料には、無
機および有機材料が用いられ、その代表として、モノア
ゾ顔料、ジスアゾ顔料、トリスアゾ顔料、ペリレン系顔
料、ペリノン系顔料、キナクリドン系顔料、キノン系縮
合多環化合物、スクアリック酸系染料、フタロシアニン
系顔料、ナフタロシアニン系顔料、アズレニウム塩系染
料、セレン、セレン−テルル、セレン−ヒ素合金、アモ
ルファス・シリコン等が挙げられる。Next, the photosensitive layer 15 will be described. For convenience of description, the case where the charge generation layer 17 and the charge transport layer 19 are stacked will be described first. The charge generation layer 17 is a layer containing a charge generation material as a main component. As the charge generation material, inorganic and organic materials are used, and representative examples thereof include monoazo pigments, disazo pigments, trisazo pigments, perylene pigments, perinone pigments, quinacridone pigments, quinone condensed polycyclic compounds, and squaric acid dyes. , Phthalocyanine pigments, naphthalocyanine pigments, azurenium salt dyes, selenium, selenium-tellurium, selenium-arsenic alloys, and amorphous silicon.
【００１０】電荷発生材料は、単独であるいは、２種以
上混合して用いられる。電荷発生層１７は、電荷発生材
料を適宜用いられるバインダー樹脂とともに、テトラヒ
ドロフラン、シクロヘキサノン、ジオキサン、２−ブタ
ノン、ジクロルエタン等の適当な溶媒を用いてボールミ
ル、アトライター、サンドミルなどにより分散し、分散
液を塗布することにより形成できる。塗布は、浸漬塗工
法やスプレーコート、ビードコート法などを用いて行な
うことができる。The charge generating materials may be used alone or in combination of two or more. The charge generation layer 17 is formed by dispersing a charge generation material with a binder resin, which is appropriately used, using a ball mill, attritor, sand mill, or the like, using a suitable solvent such as tetrahydrofuran, cyclohexanone, dioxane, 2-butanone, or dichloroethane. It can be formed by coating. The coating can be performed by using a dip coating method, a spray coating method, a bead coating method, or the like.
【００１１】適宜用いられるバインダー樹脂としては、
ポリアミド、ポリウレタン、ポリエステル、エポキシ樹
脂、ポリケトン、ポリカーボネート、シリコーン樹脂、
アクリル樹脂、ポリビニルブチラール、ポリビニルホル
マール、ポリビニルケトン、ポリスチレン、ポリアクリ
ルアミドなどが挙げられ用いられる。適宜用いられるバ
インダー樹脂の量は、電荷発生材料１重量部に対して０
〜２重量部が適当である。As the binder resin used appropriately,
Polyamide, polyurethane, polyester, epoxy resin, polyketone, polycarbonate, silicone resin,
Acrylic resin, polyvinyl butyral, polyvinyl formal, polyvinyl ketone, polystyrene, polyacrylamide and the like can be used. The amount of the binder resin used appropriately is 0 with respect to 1 part by weight of the charge generation material.
~ 2 parts by weight is suitable.
【００１２】電荷発生層１７は、また、公知の真空薄膜
作製法にても設けることができる。電荷発生層１７の膜
厚は、０．０１〜５μｍ程度が適当であり、好ましくは
０．１〜２μｍである。The charge generation layer 17 can also be provided by a known vacuum thin film forming method. The film thickness of the charge generation layer 17 is suitably about 0.01 to 5 μm, preferably 0.1 to 2 μm.
【００１３】電荷輸送層１９は、電荷輸送材料およびバ
インダー樹脂を適当な溶剤に溶解ないし分散し、これを
塗布、乾燥することにより形成できる。また、必要によ
り可塑剤やレべリング剤等を添加することもできる。The charge transport layer 19 can be formed by dissolving or dispersing a charge transport material and a binder resin in a suitable solvent, coating and drying the solution. If necessary, a plasticizer, a leveling agent, etc. may be added.
【００１４】電荷輸送材料は、上述した一般式（Ｉ）で
示される化合物と一般式（ＩＩＩ）、（Ｖ）ないし（Ｉ
Ｘ）でそれぞれ示される化合物から選択された少なくと
も１種とが混合して用いられる。これら化合物の具体例
を下記表１および表２ないし表７に挙げる。これら化合
物の混合比は、一般式（Ｉ）で示される化合物と一般式
（ＩＩＩ）、（Ｖ）ないし（ＩＸ）でそれぞれ示される
化合物から選択された少なくとも１種とが、５：９５〜
９５：５の範囲にあると良好な結果が得られる。また、
これら電荷輸送材料の使用量は、積層感光体では電荷輸
送層の全構成材料に対して１５ないし７５重量％、好ま
しくは２５ないし６５重量％である。The charge-transporting material includes the compound represented by the general formula (I) and the general formulas (III), (V) to (I ).
At least one selected from the compounds represented by X) is used in mixture. Specific examples of these compounds are shown in Table 1 and Tables 2 to 7 below. The mixing ratio of these compounds, a compound represented by the general formula (I) and the general formula
(III), at least one selected from the compounds represented by (V) to (IX) are 5: 95-
Good results are obtained in the range of 95: 5. Also,
The amount of these charge-transporting materials used is 15 to 75% by weight, preferably 25 to 65% by weight, based on the total components of the charge-transporting layer in the laminated photoreceptor.
【００１５】[0015]
【表１−（１）】 [Table 1- (1)]
【００１６】[0016]
【表１−（２）】 [Table 1- (2)]
【００１７】[0017]
【表１−（３）】 [Table 1- (3)]
【００１８】[0018]
【表１−（４）】 [Table 1- (4)]
【００１９】[0019]
【表１−（５）】 [Table 1- (5)]
【００２０】[0020]
【表１−（６）】 [Table 1- (6)]
【００２１】[0021]
【表１−（７）】 [Table 1- (7)]
【００２２】[0022]
【表１−（８）】 [Table 1- (8)]
【００２３】[0023]
【表１−（９）】 [Table 1- (9)]
【００２４】[0024]
【表２】 [Table 2]
【００２５】[0025]
【表３−（１）】 [Table 3- (1)]
【００２６】[0026]
【表３−（２）】 [Table 3- (2)]
【００２７】[0027]
【表３−（３）】 [Table 3- (3)]
【００２８】[0028]
【表３−（４）】 [Table 3- (4)]
【００２９】[0029]
【表３−（５）】 [Table 3- (5)]
【００３０】[0030]
【表３−（６）】 [Table 3- (6)]
【００３１】[0031]
【表３−（７）】 [Table 3- (7)]
【００３２】[0032]
【表３−（８）】 [Table 3- (8)]
【００３３】[0033]
【表３−（９）】 [Table 3- (9)]
【００３４】[0034]
【表４−（１）】 [Table 4- (1)]
【００３５】[0035]
【表４−（２）】 [Table 4- (2)]
【００３６】[0036]
【表５−（１）】 [Table 5- (1)]
【００３７】[0037]
【表５−（２）】 [Table 5- (2)]
【００３８】[0038]
【表５−（３）】 [Table 5- (3)]
【００３９】[0039]
【表５−（４）】 [Table 5- (4)]
【００４０】[0040]
【表６−（１）】 [Table 6- (1)]
【００４１】[0041]
【表６−（２）】 [Table 6- (2)]
【００４２】[0042]
【表７−（１）】 [Table 7- (1)]
【００４３】[0043]
【表７−（２）】 [Table 7- (2)]
【００４４】[0044]
【表７−（３）】 [Table 7- (3)]
【００４５】[0045]
【表７−（４）】 [Table 7- (4)]
【００４６】[0046]
【表７−（５）】 [Table 7- (5)]
【００４７】[0047]
【表７−（６）】 [Table 7- (6)]
【００４８】また、一般式（Ｉ）で示される化合物と一
般式（ＩＩＩ）、（Ｖ）ないし（ＩＸ）でそれぞれ示さ
れる化合物から選択された少なくとも１種とからなる電
荷輸送材料のほかに、さらに公知の電子輸送性電荷輸送
材料および／または正孔輸送性電荷輸送材料を併用して
もよい。Further, in addition to the charge transport material comprising the compound represented by the general formula (I) and at least one selected from the compounds represented by the general formulas (III), (V) to (IX), Further, a known electron transporting charge transporting material and / or hole transporting charge transporting material may be used in combination.
【００４９】電荷輸送材料とともに電荷輸送層１９に使
用されるバインダー樹脂としては、ポリスチレン、スチ
レン−アクリロニトリル共重合体、スチレン−ブタジエ
ン共重合体、スチレン−無水マレイン酸共重合体、ポリ
エステル、ポリ塩化ビニル、塩化ビニル−酢酸ビニル共
重合体、ポリ酢酸ビニル、ポリ塩化ビニリデン、ポリア
リレート、フェノキシ樹脂、ポリカーボネート、酢酸セ
ルロース樹脂、エチルセルロース樹脂、ポリビニルブチ
ラール、ポリビニルホルマール、ポリビニルトルエン、
アクリル樹脂、シリコーン樹脂、エポキシ樹脂、メラミ
ン樹脂、ウレタン樹脂、フェノール樹脂、アルキッド樹
脂等の熱可塑性、または熱硬化性樹脂が挙げられる。As the binder resin used in the charge transport layer 19 together with the charge transport material, polystyrene, styrene-acrylonitrile copolymer, styrene-butadiene copolymer, styrene-maleic anhydride copolymer, polyester, polyvinyl chloride are used. , Vinyl chloride-vinyl acetate copolymer, polyvinyl acetate, polyvinylidene chloride, polyarylate, phenoxy resin, polycarbonate, cellulose acetate resin, ethyl cellulose resin, polyvinyl butyral, polyvinyl formal, polyvinyl toluene,
Examples thereof include thermoplastic or thermosetting resins such as acrylic resins, silicone resins, epoxy resins, melamine resins, urethane resins, phenol resins, and alkyd resins.
【００５０】溶剤としては、テトラヒドロフラン、ジオ
キサン、トルエン、２−ブタノン、モノクロルベンゼ
ン、ジクロルエタン、塩化メチレンなどが用いられる。
電荷輸送層１９の厚さは、５〜１００μｍが適当であ
る。As the solvent, tetrahydrofuran, dioxane, toluene, 2-butanone, monochlorobenzene, dichloroethane, methylene chloride or the like is used.
The appropriate thickness of the charge transport layer 19 is 5 to 100 μm.
【００５１】本発明において、電荷輸送層１９中に可塑
剤やレべリング剤を添加してもよい。可塑剤としては、
ジブチルフタレート、ジオクチルフタレートなど一般の
樹脂の可塑剤として使用されているものがそのまま使用
でき、その使用量は、バインダー樹脂に対して０〜３０
重量％程度が適当である。レベリング剤としては、ジメ
チルシリコーンオイル、メチルフェニルシリコーンオイ
ルなどのシリコーンオイル類や、側鎖にパーフルオロア
ルキル基を有するポリマーあるいはオリゴマーが使用さ
れ、その使用量はバインダー樹脂に対して、０〜１重量
％が適当である。In the present invention, a plasticizer or a leveling agent may be added to the charge transport layer 19. As a plasticizer,
What is used as a plasticizer for general resins such as dibutyl phthalate and dioctyl phthalate can be used as it is, and the amount thereof is 0 to 30 relative to the binder resin.
About wt% is appropriate. As the leveling agent, silicone oils such as dimethyl silicone oil and methylphenyl silicone oil, and polymers or oligomers having a perfluoroalkyl group in the side chain are used, and the amount thereof is 0 to 1 weight with respect to the binder resin. % Is appropriate.
【００５２】次に感光層１５が単層構成の場合について
述べる。この場合に用いられる材料も多くは電荷発生材
料と電荷輸送材料よりなる機能分離型で用いられるもの
と同じものが挙げられる。Next, the case where the photosensitive layer 15 has a single layer structure will be described. Many of the materials used in this case are the same as those used in the function separation type composed of a charge generating material and a charge transporting material.
【００５３】即ち、少なくとも電荷発生材料および一般
式（Ｉ）で示される化合物と一般式（ＩＩＩ）、（Ｖ）
ないし（ＩＸ）でそれぞれ示される化合物から選択され
た少なくとも１種とからなる電荷輸送材料を、バインダ
ー樹脂とともに適当な溶剤に溶解ないし分散し、これを
塗布、乾燥することによって形成できる。また、必要に
より可塑剤やしべリング剤等を添加することもできる。
バインダー樹脂としては、先に電荷輸送層１９で挙げた
バインダー樹脂をそのまま用いることができるほかに、
電荷発生層１７で挙げたバインダー樹脂を混合してもよ
い。That is, at least the charge generation material and the compound represented by the general formula (I) and the general formulas (III) and (V)
To (IX), a charge transporting material composed of at least one selected from the compounds represented by formulas (IX) to (IX) is dissolved or dispersed in a suitable solvent together with a binder resin, and this is applied and dried. Further, if necessary, a plasticizer, a leveling agent, etc. may be added.
As the binder resin, the binder resins mentioned above in the charge transport layer 19 can be used as they are,
The binder resins mentioned for the charge generation layer 17 may be mixed.
【００５４】ピリリウム系染料、ビスフェノールＡ系ポ
リカーボネートから形成される共晶錯体に一般式（Ｉ）
で示される化合物と一般式（ＩＩＩ）、（Ｖ）ないし
（ＩＸ）でそれぞれ示される化合物から選択された少な
くとも１種とからなる電荷輸送材料を添加した感光層も
単層感光層として用いることができる。The eutectic complex formed from pyrylium dye and bisphenol A polycarbonate is represented by the general formula (I)
And a compound represented by the general formula (III), (V) or
A photosensitive layer to which a charge transport material composed of at least one selected from the compounds represented by (IX) is added can also be used as the single-layer photosensitive layer.
【００５５】さらに、一般式（Ｉ）で示される化合物と
一般式（ＩＩＩ）、（Ｖ）ないし（ＩＸ）でそれぞれ示
される化合物から選択された少なくとも１種とからなる
電荷輸送材料およびバインダー樹脂を主成分としてな
り、電荷発生材料を有効成分として含まない単層感光層
も青色光〜紫外光に感度を有する感光体として有用であ
る。Furthermore, a charge transporting material and a binder resin each comprising a compound represented by the general formula (I) and at least one selected from compounds represented by the general formulas (III), (V) to (IX) are used. A single-layer photosensitive layer which is a main component and does not contain a charge generating material as an effective component is also useful as a photoreceptor having sensitivity to blue light to ultraviolet light.
【００５６】単層感光層における上記特定の２種類の電
荷輸送材料の混合比は、積層感光層の場合と同様、５：
９５〜９５：５の範囲が好ましく、その使用量は単層感
光層の全構成材料に対して５ないし７５重量％、好まし
くは１０〜６５重量％である。また、単層感光層の膜厚
は５〜１００μｍが適当である。The mixing ratio of the above-mentioned specific two kinds of charge transport materials in the single-layer photosensitive layer is 5: as in the case of the laminated photosensitive layer.
The range of 95 to 95: 5 is preferable, and the amount used is 5 to 75% by weight, preferably 10 to 65% by weight, based on all the constituent materials of the single-layer photosensitive layer. Further, the thickness of the single-layer photosensitive layer is appropriately 5 to 100 μm.
【００５７】本発明の電子写真感光体には、導電性支持
体１１と感光層との間に下引き層を設けることができ
る。下引き層は一般に樹脂を主成分とするが、これらの
樹脂はその上に感光層を溶剤でもって塗布することを考
えると、一般の有機溶剤に対して耐溶解性の高い樹脂で
あることが望ましい。このような樹脂としては、ポリビ
ニルアルコール、カゼイン、ポリアクリル酸ナトリウム
等の水溶性樹脂、共重合ナイロン、メトキシメチル化ナ
イロン等のアルコール可溶性樹脂、ポリウレタン、メラ
ミン樹脂、アルキッド−メラミン樹脂、エポキシ樹脂
等、三次元網目構造を形成する硬化型樹脂などが挙げら
れる。The electrophotographic photosensitive member of the present invention may be provided with an undercoat layer between the conductive support 11 and the photosensitive layer. The undercoat layer generally contains a resin as a main component, but considering that the resin is coated with a photosensitive layer on the resin, it is considered that the resin is a resin having high solubility in a general organic solvent. desirable. Examples of such resins include polyvinyl alcohol, casein, water-soluble resins such as sodium polyacrylate, copolymerized nylon, alcohol-soluble resins such as methoxymethylated nylon, polyurethane, melamine resin, alkyd-melamine resin, and epoxy resin. Examples thereof include curable resins that form a three-dimensional network structure.
【００５８】また、下引き層にはモアレ防止、残留電位
の低減等のために酸化チタン、シリカ、アルミナ、酸化
ジルコニウム、酸化スズ、酸化インジウム等で例示でき
る金属酸化物の微粉末を加えてもよい。これらの下引き
層は、前述の感光層のごとく適当な溶媒、塗工法を用い
て形成することができる。To the undercoat layer, fine powders of metal oxides such as titanium oxide, silica, alumina, zirconium oxide, tin oxide and indium oxide can be added to prevent moire and reduce residual potential. Good. These undercoat layers can be formed by using an appropriate solvent and coating method like the above-mentioned photosensitive layer.
【００５９】更に本発明の下引き層として、シランカッ
プリング剤、チタンカップリング剤、クロムカップリン
グ剤等を使用して、例えばゾル−ゲル法等により形成し
た金属酸化物層も有用である。Further, as the undercoat layer of the present invention, a metal oxide layer formed by using, for example, a sol-gel method using a silane coupling agent, a titanium coupling agent, a chromium coupling agent or the like is also useful.
【００６０】この他に、本発明の下引き層にはＡｌ２Ｏ
３を陽極酸化にて設けたものや、ポリパラキシリレン
（パリレン）等の有機物や、ＳｉＯ、ＳｎＯ２、ＴｉＯ
２、ＩＴＯ、ＣｅＯ２等の無機物を真空薄膜作製法にて
設けたものも良好に使用できる。下引き層の膜厚は０〜
５μｍが適当である。In addition, Al 2 O is used as the undercoat layer of the present invention.
3 provided by anodic oxidation, organic substances such as polyparaxylylene (parylene), SiO, SnO 2 , TiO 2 .
Those provided with an inorganic substance such as 2 , ITO or CeO 2 by a vacuum thin film forming method can also be used favorably. The thickness of the undercoat layer is 0
5 μm is suitable.
【００６１】本発明の電子写真感光体には、感光層保護
の目的で、保護層が感光層の上に設けられることもあ
る。これに使用される材料としては、ＡＢＳ樹脂、ＡＣ
Ｓ樹脂、オレフィン〜ビニルモノマー共重合体、塩素化
ポリエーテル、アリル樹脂、フェノール樹脂、ポリアセ
タール、ポリアミド、ポリアミドイミド、ポリアクリレ
ート、ポリアリルスルホン、ポリブチレン、ポリブチレ
ンテレフタレート、ポリカーボネート、ポリエーテルス
ルホン、ポリエチレン、ポリエチレンテレフタレート、
ポリイミド、アクリル樹脂、ポリメチルペンテン、ポリ
プロピレン、ポリフェニレンオキシド、ポリスルホン、
ＡＳ樹脂、ＡＢ樹脂、ＢＳ樹脂、ポリウレタン、ポリ塩
化ビニル、ポリ塩化ビニリデン、エポキシ樹脂等の樹脂
が挙げられる。In the electrophotographic photoreceptor of the present invention, a protective layer may be provided on the photosensitive layer for the purpose of protecting the photosensitive layer. Materials used for this are ABS resin, AC
S resin, olefin-vinyl monomer copolymer, chlorinated polyether, allyl resin, phenol resin, polyacetal, polyamide, polyamideimide, polyacrylate, polyallyl sulfone, polybutylene, polybutylene terephthalate, polycarbonate, polyether sulfone, polyethylene, polyethylene terephthalate,
Polyimide, acrylic resin, polymethylpentene, polypropylene, polyphenylene oxide, polysulfone,
Examples thereof include resins such as AS resin, AB resin, BS resin, polyurethane, polyvinyl chloride, polyvinylidene chloride, and epoxy resin.
【００６２】保護層にはその他、耐摩耗性を向上する目
的で、ポリテトラフルオロエチレンのようなフッ素樹
脂、シリコーン樹脂およびこれら樹脂に酸化チタン、酸
化スズ、チタン酸カリウム等の無機材料を分散したもの
等を添加することができる。保護層の形成法としては、
通常の塗布法が採用される。なお、保護層の厚さは、
０．５〜１０μｍ程度が適当である。また、以上のほか
に真空薄膜作製法にて形成したｉ−Ｃ，ａ−ＳｉＣなど
公知の材料も保護層として用いることができる。本発明
においては、感光層と保護層との間に別の中間層を設け
ることも可能である。中間層には、一般にバインダー樹
脂を主成分として用いる。これら樹脂としては、ポリア
ミド、アルコール可溶性ナイロン、水溶性ポリビニルブ
チラール、ポリビニルブチラール、ポリビニルアルコー
ルなどが挙げられる。中間層の形成法としては、前述の
ごとく通常の塗布法が採用される。なお、中間層の厚さ
は０．０５〜２μｍ程度が適当である。For the purpose of improving wear resistance, the protective layer has a fluororesin such as polytetrafluoroethylene, a silicone resin, and an inorganic material such as titanium oxide, tin oxide or potassium titanate dispersed in these resins. The thing etc. can be added. As a method of forming the protective layer,
The usual coating method is adopted. The thickness of the protective layer is
About 0.5 to 10 μm is suitable. In addition to the above, known materials such as i-C and a-SiC formed by the vacuum thin film manufacturing method can also be used as the protective layer. In the present invention, it is possible to provide another intermediate layer between the photosensitive layer and the protective layer. A binder resin is generally used as a main component in the intermediate layer. Examples of these resins include polyamide, alcohol-soluble nylon, water-soluble polyvinyl butyral, polyvinyl butyral, and polyvinyl alcohol. As a method of forming the intermediate layer, a usual coating method is adopted as described above. The thickness of the intermediate layer is preferably about 0.05 to 2 μm.
【００６３】[0063]
【実施例】次に実施例を示すが、実施例は本発明を詳し
く説明するものであり、本発明が実施例によって制約さ
れるものではない。なお、実施例中の部はすべて重量部
である。EXAMPLES Examples will be shown below, but the examples explain the present invention in detail, and the present invention is not limited to the examples. All parts in the examples are parts by weight.
【００６４】先ず電荷輸送材料として一般式（Ｉ）で示
される化合物と一般式（ＩＩＩ）で示される化合物を併
用した場合について、実施例９〜１６および比較例９〜
１６により説明する。 First, in the case where the compound represented by the general formula (I) and the compound represented by the general formula (III) are used in combination as the charge transport material, Examples 9 to 16 and Comparative Examples 9 to
This will be described with reference to 16.
【００６５】〔実施例１〕
外径７０ｍｍのアルミニウムシリンダー上に、下記組成
の下引層塗工液、電荷発生層塗工液、電荷輸送層塗工液
を順次、塗布・乾燥して各々４μｍの下引層、０．２μ
ｍの電荷発生層、２２μｍの電荷輸送層を形成し、本発
明の電子写真感光体を作製した。
Example 1 An undercoat layer coating solution, a charge generating layer coating solution, and a charge transporting layer coating solution having the following compositions were sequentially coated and dried on an aluminum cylinder having an outer diameter of 70 mm to 4 μm each. Undercoat layer, 0.2μ
A charge generation layer having a thickness of m and a charge transport layer having a thickness of 22 μm were formed to prepare an electrophotographic photoreceptor of the present invention.
【化１７】 [Chemical 17]
【００６６】〔比較例１〕
実施例１の電荷輸送層塗工液を下記組成のものに変えた
以外は実施例１と同様にして比較例の電子写真感光体を
作製した。
Comparative Example 1 An electrophotographic photoreceptor of Comparative Example was prepared in the same manner as in Example 1 except that the coating solution for the charge transport layer in Example 1 was changed to the one having the following composition.
【００６７】〔実施例２〕
アルミニウムシリンダー表面を陽極酸化処理した後、封
孔処理を行った。この上に、下記電荷発生層塗工液、電
荷輸送層塗工液を順次塗布・乾燥して各々０．２μｍの
電荷発生層、２０μｍの電荷輸送層を形成し本発明の電
子写真感光体を作製した。
Example 2 The surface of an aluminum cylinder was anodized and then sealed. The following charge generating layer coating liquid and charge transporting layer coating liquid are successively applied and dried to form a charge generating layer of 0.2 μm and a charge transporting layer of 20 μm, respectively. It was made.
【化１８】 [Chemical 18]
【００６８】〔比較例２〕
実施例２の電荷輸送層塗工液において、化合物ＮＯ．Ｉ
ＩＩ−１６の化合物を添加しないこと以外は実施例２と
同様にして比較例の電子写真感光体を作製した。[Comparative Example 2 ] In the charge transport layer coating liquid of Example 2 , the compound NO. I
An electrophotographic photoreceptor of Comparative Example was produced in the same manner as in Example 2 except that the compound of II-16 was not added.
【００６９】〔実施例３〕
アルミニウムシリンダー上に、下記組成の下引層塗工
液、下記組成の電荷発生層塗工液、下記組成の電荷輸送
層塗工液を、順次塗布・乾燥して各々２μｍの下引層、
０．２μｍの電荷発生層、２μｍの電荷輸送層を形成
し、本発明の電子写真感光体を作製した。
Example 3 An undercoat layer coating solution having the following composition, a charge generating layer coating solution having the following composition, and a charge transport layer coating solution having the following composition were sequentially applied and dried on an aluminum cylinder. 2 μm each undercoat layer,
A charge generation layer having a thickness of 0.2 μm and a charge transport layer having a thickness of 2 μm were formed to prepare an electrophotographic photoreceptor of the present invention.
【化１９】 [Chemical 19]
【００７０】〔比較例３〕
実施例３の電荷輸送層塗工液を下記組成のものにした以
外は実施例３と同様にして比較例の電子写真感光体を作
製した。
Comparative Example 3 An electrophotographic photosensitive member of Comparative Example was prepared in the same manner as in Example 3 except that the coating solution for the charge transport layer of Example 3 had the following composition.
【００７１】〔実施例４〕
実施例１の電荷輸送層塗工液を下記組成のものにした以
外は実施例１と同様にして本発明の電子写真感光体を作
製した。
Example 4 An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 1 except that the coating solution for the charge transport layer of Example 1 had the following composition.
【００７２】〔比較例４〕
実施例４の電荷輸送層塗工液を下記組成のものにした以
外は実施例４と同様にして比較例の電子写真感光体を作
製した。
Comparative Example 4 An electrophotographic photoreceptor of Comparative Example was prepared in the same manner as in Example 4 , except that the coating solution for charge transport layer of Example 4 had the following composition.
【００７３】〔実施例５〕
実施例２の電荷輸送層塗工液を下記組成のものにした以
外は実施例２と同様にして本発明の電子写真感光体を作
製した。
Example 5 An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 2 except that the coating solution for the charge transport layer of Example 2 had the following composition.
【００７４】〔比較例５〕
実施例５の電荷輸送層塗工液を下記組成のものにした以
外は実施例５と同様にして比較例の電子写真感光体を作
製した。
Comparative Example 5 An electrophotographic photosensitive member of Comparative Example was prepared in the same manner as in Example 5 , except that the coating solution for charge transport layer of Example 5 had the following composition.
【００７５】〔実施例６〕
実施例３の電荷輸送層塗工液を下記組成のものにした以
外は実施例３と同様にして本発明の電子写真感光体を作
製した。
Example 6 An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 3 except that the coating solution for charge transport layer in Example 3 had the following composition.
【００７６】〔比較例６〕
実施例６の電荷輸送層塗工液において、化合物ＮＯ．Ｉ
−１２の化合物を添加しないこと以外は実施例６と同様
にして比較例の電子写真感光体を作製した。[Comparative Example 6 ] In the charge transport layer coating liquid of Example 6 , the compound NO. I
An electrophotographic photoreceptor of Comparative Example was produced in the same manner as in Example 6 except that the compound of −12 was not added.
【００７７】〔実施例７〕
アルミニウムシリンダー上に、下記組成の共晶錯体光導
電層塗工液を塗布・乾燥し、厚さ２５μｍの共晶錯体光
導電層を形成し本発明の電子写真感光体を作製した。
Example 7 An eutectic complex photoconductive layer coating solution having the following composition was applied onto an aluminum cylinder and dried to form a eutectic complex photoconductive layer having a thickness of 25 μm. The body was made.
【００７８】〔比較例７〕
実施例７の電荷輸送層塗工液において、化合物ＮＯ．Ｉ
ＩＩ−２の化合物を添加しないこと以外は実施例７と同
様にして比較例の電子写真感光体を作製した。[Comparative Example 7 ] In the charge transport layer coating liquid of Example 7 , the compound NO. I
An electrophotographic photoreceptor of Comparative Example was produced in the same manner as in Example 7 except that the compound of II-2 was not added.
【００７９】〔実施例８〕
アルミニウムシリンダー上に、下記組成の感光層塗工液
を塗布・乾燥し、厚さ２３μｍの単層感光層を形成し本
発明の電子写真感光体を作製した。
Example 8 A photosensitive layer coating solution having the following composition was applied onto an aluminum cylinder and dried to form a single-layer photosensitive layer having a thickness of 23 μm to prepare an electrophotographic photoreceptor of the present invention.
【化２０】 [Chemical 20]
【００８０】〔比較例８〕
アルミニウムシリンダー上に、下記組成の感光層塗工液
を塗布・乾燥し、厚さ２３μｍの単層感光層を形成し比
較例の電子写真感光体を作製した。
Comparative Example 8 A photosensitive layer coating liquid having the following composition was applied onto an aluminum cylinder and dried to form a single-layer photosensitive layer having a thickness of 23 μm, to prepare an electrophotographic photosensitive member of Comparative Example.
【００８１】実施例１〜８および比較例１〜８で得られ
た各感光体について、次に示す方法で感光体特性を測定
した。結果を表８に示す。[0081] For each of the photoreceptors obtained in Examples 1-8 and Comparative Examples 1-8, the photosensitive member properties were measured by the following method. The results are shown in Table 8 .
【００８２】以上の実施例及び比較例の各感光体を特開
昭６０−１００１６７号公報に開示されてい る評価装置
を用いて次のような測定を行なった。コロナ放電電圧−
６．０ｋＶ（または＋５．６ｋＶ）で帯電２０秒後の電
位Ｖｍ（Ｖ）、暗減衰２０秒後の電位Ｖｏ（Ｖ）、強度
６ｌｕｘの白色光による露光２０秒後の残留電位ＶＲ
（Ｖ）、更に電位Ｖｏを１／２に減衰させるのに必要な
露光量Ｅ１／２［ｌｕｘ・ｓｅｃ］を測定した。電位保
持率＝Ｖｏ／Ｖｍと定義する。また、各感光体をリコー
製複写機ＦＴ−３３００（ないしは感光体を正帯電でき
るように改造したもの）に搭載して連続３万枚の複写を
行い、異常画像の有無を目視により判定した。また、複
写試験終了後の各感光体は、上記と同じ方法で感光体特
性を測定した。 Each of the photoconductors of the above Examples and Comparative Examples was disclosed
That it has been disclosed in Japanese Sho 60-100167 evaluation device
The following measurements were performed using the. Corona discharge voltage −
Charging at 6.0 kV (or +5.6 kV), charging after 20 seconds
Vm (V), potential Vo (V) after 20 seconds of dark decay, intensity
Residual potential VR after 20 seconds of exposure with 6 lux of white light
(V), necessary to further attenuate the potential Vo by half
The exposure amount E1 / 2 [lux · sec] was measured. Potential
Proportion is defined as Vo / Vm. In addition, each photoconductor is
Copier FT-3300 (or photoconductor can be positively charged)
It has been modified so that it can be used to copy 30,000 consecutive copies.
Then, the presence or absence of an abnormal image was visually determined. In addition,
After the copying test, each photoconductor is treated in the same way as above.
The sex was measured.
【００８３】[0083]
【表８】 [Table 8]
【００８４】次に電荷輸送材料として一般式Ｉで示され
る化合物と一般式Ｖで示される化合物を併用した場合に
ついて、実施例９から１６および比較例９から１６によ
り説明する。Next, the case where the compound represented by the general formula I and the compound represented by the general formula V are used in combination as the charge transport material will be described with reference to Examples 9 to 16 and Comparative Examples 9 to 16 .
【００８５】〔実施例９〕
外径７０ｍｍのアルミニウムシリンダー上に下記組成の
下引層塗工液、電荷発生層塗工液、電荷輸送層塗工液を
順次、塗布・乾燥して各々４μｍの下引層、０．２μｍ
の電荷発生層、２２μｍの電荷輸送層を形成し、本発明
の電子写真感光体を作製した。
Example 9 An undercoat layer coating solution, a charge generating layer coating solution, and a charge transport layer coating solution having the following compositions were sequentially coated and dried on an aluminum cylinder having an outer diameter of 70 mm to a thickness of 4 μm. Subbing layer, 0.2 μm
The charge generation layer and the charge transport layer having a thickness of 22 μm were formed to prepare the electrophotographic photoreceptor of the present invention.
【化１３】 [Chemical 13]
【００８６】〔比較例９〕
実施例９の電荷輸送層塗工液を下記組成のものに変えた
以外は実施例９と同様にして比較例の電子写真感光体を
作製した。
Comparative Example 9 An electrophotographic photosensitive member of Comparative Example was prepared in the same manner as in Example 9 except that the coating solution for the charge transport layer of Example 9 was changed to the composition shown below.
【００８７】〔実施例１０〕
アルミニウムシリンダー表面を陽極酸化処理した後、封
孔処理を行った。この上に、下記電荷発生層塗工液、電
荷輸送層塗工液を順次塗布・乾燥して各々０．２μｍの
電荷発生層、２０μｍの電荷輸送層を形成し本発明の電
子写真感光体を作製した。
Example 10 The surface of an aluminum cylinder was anodized and then sealed. The following charge generating layer coating liquid and charge transporting layer coating liquid are successively applied and dried to form a charge generating layer of 0.2 μm and a charge transporting layer of 20 μm, respectively. It was made.
【化１４】 [Chemical 14]
【００８８】〔比較例１０〕
実施例１０の電荷輸送層塗工液において、化合物ＮＯ．
Ｖ−２５の化合物を添加しないこと以外は実施例１０と
同様にして比較例の電子写真感光体を作製した。Comparative Example 10 In the charge transport layer coating liquid of Example 10 , the compound NO.
An electrophotographic photoreceptor of Comparative Example was produced in the same manner as in Example 10 except that the compound of V-25 was not added.
【００８９】〔実施例１１〕
アルミニウムシリンダー上に下記組成の下引層塗工液、
下記組成の電荷発生層塗工液、下記組成の電荷輸送層塗
工液を、順次塗布・乾燥して各々２μｍの下引層、０．
２μｍの電荷発生層、２μｍの電荷輸送層を形成し、本
発明の電子写真感光体を作製した。
Example 11 A subbing layer coating solution having the following composition on an aluminum cylinder,
A charge generation layer coating solution having the following composition and a charge transport layer coating solution having the following composition were sequentially applied and dried to form an undercoat layer of 2 μm each.
A 2 μm charge generation layer and a 2 μm charge transport layer were formed to prepare an electrophotographic photoreceptor of the present invention.
【化１５】 [Chemical 15]
【００９０】〔比較例１１〕
実施例１１の電荷輸送層塗工液を下記組成のものにした
以外は実施例２７と同様にして比較例の電子写真感光体
を作製した。
Comparative Example 11 An electrophotographic photoreceptor of Comparative Example was prepared in the same manner as in Example 27, except that the coating solution for charge transport layer of Example 11 had the following composition.
【００９１】〔実施例１２〕
実施例９の電荷輸送層塗工液を下記組成のものにした以
外は実施例９と同様にして本発明の電子写真感光体を作
製した。
Example 12 An electrophotographic photosensitive member of the present invention was prepared in the same manner as in Example 9 except that the coating solution for charge transport layer in Example 9 had the following composition.
【００９２】〔比較例１２〕
実施例１２の電荷輸送層塗工液を下記組成のものにした
以外は実施例１２と同様にして比較例の電子写真感光体
を作製した。
Comparative Example 12 An electrophotographic photoreceptor of Comparative Example was prepared in the same manner as in Example 12 except that the coating solution for charge transport layer of Example 12 had the following composition.
【００９３】〔実施例１３〕
実施例１０の電荷輸送層塗工液を下記組成のものにした
以外は実施例１０と同様にして本発明の電子写真感光体
を作製した。
Example 13 An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 10 except that the coating solution for charge transport layer of Example 10 had the following composition.
【００９４】〔比較例１３〕
実施例１３の電荷輸送層塗工液を下記組成のものにした
以外は実施例１３と同様にして比較例の電子写真感光体
を作製した。
Comparative Example 13 An electrophotographic photoreceptor of Comparative Example was prepared in the same manner as in Example 13 except that the coating solution for charge transport layer of Example 13 had the following composition.
【００９５】〔実施例１４〕
実施例１１の電荷輸送層塗工液を下記組成のものにした
以外は実施例１１と同様にして本発明の電子写真感光体
を作製した。
Example 14 An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 11 except that the coating solution for charge transport layer of Example 11 had the following composition.
【００９６】〔比較例１４〕
実施例１４の電荷輸送層塗工液において、化合物ＮＯ．
Ｉ−７５の化合物を添加しないこと以外は実施例１４と
同様にして比較例の電子写真感光体を作製した。[Comparative Example 14 ] In the charge transport layer coating liquid of Example 14 , the compound NO.
An electrophotographic photoreceptor of Comparative Example was produced in the same manner as in Example 14 except that the compound of I-75 was not added.
【００９７】〔実施例１５〕
アルミニウムシリンダー上に下記組成の共晶錯体光導電
層塗工液を塗布・乾燥し、厚さ２５μｍの共晶錯体光導
電層を形成し本発明の電子写真感光体を作製した。
Example 15 An electrophotographic photosensitive member of the present invention was prepared by coating a eutectic complex photoconductive layer coating solution having the following composition on an aluminum cylinder and drying it to form a eutectic complex photoconductive layer having a thickness of 25 μm. Was produced.
【００９８】〔比較例１５〕
実施例１５の電荷輸送層塗工液において、化合物ＮＯ．
Ｖ−４６の化合物を添加しないこと以外は実施例１５と
同様にして比較例の電子写真感光体を作製した。Comparative Example 15 In the charge transport layer coating liquid of Example 15 , the compound NO.
An electrophotographic photoreceptor of Comparative Example was produced in the same manner as in Example 15 except that the compound of V-46 was not added.
【００９９】〔実施例１６〕
アルミニウムシリンダー上に下記組成の感光層塗工液を
塗布・乾燥し、厚さ２３μｍの単層感光層を形成し本発
明の電子写真感光体を作製した。
Example 16 An electrophotographic photosensitive member of the present invention was prepared by coating a photosensitive layer coating solution having the following composition on an aluminum cylinder and drying it to form a single-layer photosensitive layer having a thickness of 23 μm.
【化１６】 [Chemical 16]
【０１００】〔比較例１６〕
アルミニウムシリンダー上に下記組成の感光層塗工液を
塗布・乾燥し、厚さ２３μｍの単層感光層を形成し比較
例の電子写真感光体を作製した。〔感光層塗工液〕
[Comparative Example 16 ] A photosensitive layer coating liquid having the following composition was applied onto an aluminum cylinder and dried to form a single-layer photosensitive layer having a thickness of 23 µm, to prepare an electrophotographic photosensitive member of Comparative Example. [Photosensitive layer coating liquid]
【０１０１】上記実施例９〜１６および比較例９〜１６
で得られた各感光体について上記と同様の方法で感光体
特性を測定した。結果を表９に示す。Examples 9 to 16 and Comparative Examples 9 to 16 above
With respect to each of the photoconductors obtained in 1., the photoconductor characteristics were measured by the same method as described above. The results are shown in Table 9 .
【０１０２】[0102]
【表９】 [Table 9]
【０１０３】次に電荷輸送材料として一般式（Ｉ）で示
される化合物と一般式（ＶＩ）で示される化合物を併用
した場合について、実施例１７〜２４および比較例１７
〜２４により説明する。Next, when the compound represented by the general formula (I) and the compound represented by the general formula (VI) were used together as the charge transport material, Examples 17 to 24 and Comparative Example 17 were used.
~ 24 will be described.
【０１０４】〔実施例１７〕
外径７０ｍｍのアルミニウムシリンダー上に下記組成の
下引層塗工液、電荷発生層塗工液、電荷輸送層塗工液を
順次、塗布・乾燥して各々４μｍの下引層、０．２μｍ
の電荷発生層、２２μｍの電荷輸送層を形成し、本発明
の電子写真感光体を作製した。
Example 17 An undercoat layer coating solution, a charge generation layer coating solution, and a charge transport layer coating solution having the following compositions were sequentially coated and dried on an aluminum cylinder having an outer diameter of 70 mm to obtain a coating solution of 4 μm each. Subbing layer, 0.2 μm
The charge generation layer and the charge transport layer having a thickness of 22 μm were formed to prepare the electrophotographic photoreceptor of the present invention.
【化２１】 [Chemical 21]
【０１０５】〔比較例１７〕
実施例１７の電荷輸送層塗工液を下記組成のものに変え
た以外は実施例１７と同様にして比較例の電子写真感光
体を作製した。
Comparative Example 17 An electrophotographic photosensitive member of Comparative Example was prepared in the same manner as in Example 17 , except that the coating solution for charge transport layer of Example 17 was changed to the composition shown below.
【０１０６】〔実施例１８〕
アルミニウムシリンダー表面を陽極酸化処理した後、封
孔処理を行った。この上に、下記電荷発生層塗工液、電
荷輸送層塗工液を順次塗布・乾燥して各々０．２μｍの
電荷発生層、２０μｍの電荷輸送層を形成し本発明の電
子写真感光体を作製した。
Example 18 The surface of an aluminum cylinder was anodized and then sealed. The following charge generating layer coating liquid and charge transporting layer coating liquid are successively applied and dried to form a charge generating layer of 0.2 μm and a charge transporting layer of 20 μm, respectively. It was made.
【化２２】 [Chemical formula 22]
【０１０７】〔比較例１８〕
実施例１８の電荷輸送層塗工液において、化合物ＮＯ．
ＶＩ−９の化合物を添加しないこと以外は実施例１８と
同様にして比較例の電子写真感光体を作製した。[Comparative Example 18 ] In the charge transport layer coating solution of Example 18 , the compound NO.
An electrophotographic photoreceptor of Comparative Example was prepared in the same manner as in Example 18 except that the compound of VI-9 was not added.
【０１０８】〔実施例１９〕
アルミニウムシリンダー上に下記組成の下引層塗工液、
下記組成の電荷発生層塗工液、下記組成の電荷輸送層塗
工液を、順次塗布・乾燥して各々２μｍの下引層、０．
２μｍの電荷発生層、２μｍの電荷輸送層を形成し、本
発明の電子写真感光体を作製した。
Example 19 A subbing layer coating solution having the following composition on an aluminum cylinder,
A charge generation layer coating solution having the following composition and a charge transport layer coating solution having the following composition were sequentially applied and dried to form an undercoat layer of 2 μm each.
A 2 μm charge generation layer and a 2 μm charge transport layer were formed to prepare an electrophotographic photoreceptor of the present invention.
【化２３】 [Chemical formula 23]
【０１０９】〔比較例１９〕
実施例１９の電荷輸送層塗工液を下記組成のものにした
以外は実施例１９と同様にして比較例の電子写真感光体
を作製した。
Comparative Example 19 An electrophotographic photosensitive member of Comparative Example was prepared in the same manner as in Example 19 except that the coating solution for the charge transport layer of Example 19 had the following composition.
【０１１０】〔実施例２０〕
実施例１７の電荷輸送層塗工液を下記組成のものにした
以外は実施例１７と同様にして本発明の電子写真感光体
を作製した。
Example 20 An electrophotographic photosensitive member of the present invention was produced in the same manner as in Example 17, except that the coating solution for charge transport layer in Example 17 had the following composition.
【０１１１】〔比較例２０〕
実施例２０の電荷輸送層塗工液を下記組成のものにした
以外は実施例２０と同様にして比較例の電子写真感光体
を作製した。
Comparative Example 20 An electrophotographic photosensitive member of Comparative Example was prepared in the same manner as in Example 20 except that the coating solution for the charge transport layer of Example 20 had the following composition.
【０１１２】〔実施例２１〕
実施例１８の電荷輸送層塗工液を下記組成のものにした
以外は実施例１８と同様にして本発明の電子写真感光体
を作製した。
Example 21 An electrophotographic photosensitive member of the present invention was produced in the same manner as in Example 18 except that the coating solution for the charge transport layer of Example 18 had the following composition.
【０１１３】〔比較例２１〕
実施例２１の電荷輸送層塗工液を下記組成のものにした
以外は実施例２１と同様にして比較例の電子写真感光体
を作製した。
Comparative Example 21 An electrophotographic photosensitive member of Comparative Example was prepared in the same manner as in Example 21 except that the coating solution for the charge transport layer of Example 21 had the following composition.
【０１１４】〔実施例２２〕
実施例１９の電荷輸送層塗工液を下記組成のものにした
以外は実施例１９と同様にして本発明の電子写真感光体
を作製した。
Example 22 An electrophotographic photosensitive member of the present invention was produced in the same manner as in Example 19 except that the coating solution for charge transport layer of Example 19 had the following composition.
【０１１５】〔比較例２２〕
実施例２２の電荷輸送層塗工液において、化合物ＮＯ．
Ｉ−７８の化合物を添加しないこと以外は実施例２２と
同様にして比較例の電子写真感光体を作製した。[Comparative Example 22 ] In the charge transport layer coating liquid of Example 22 , the compound NO.
An electrophotographic photoreceptor of Comparative Example was produced in the same manner as in Example 22 except that the compound of I-78 was not added.
【０１１６】〔実施例２３〕
アルミニウムシリンダー上に下記組成の共晶錯体光導電
層塗工液を塗布・乾燥し、厚さ２５μｍの共晶錯体光導
電層を形成し本発明の電子写真感光体を作製した。
Example 23 An eutectic complex photoconductive layer coating solution having the following composition was applied onto an aluminum cylinder and dried to form a eutectic complex photoconductive layer having a thickness of 25 μm. Was produced.
【０１１７】〔比較例２３〕
実施例２３の電荷輸送層塗工液において、化合物ＮＯ．
ＶＩ−５９の化合物を添加しないこと以外は実施例２３
と同様にして比較例の電子写真感光体を作製した。[Comparative Example 23 ] In the charge transport layer coating liquid of Example 23 , the compound NO.
Example 23 except that the compound of VI-59 was not added.
An electrophotographic photoreceptor of Comparative Example was produced in the same manner as in.
【０１１８】〔実施例２４〕
アルミニウムシリンダー上に下記組成の感光層塗工液を
塗布・乾燥し、厚さ２３μｍの単層感光層を形成し本発
明の電子写真感光体を作製した。
Example 24 An electrophotographic photosensitive member of the present invention was prepared by applying a photosensitive layer coating solution having the following composition on an aluminum cylinder and drying it to form a single-layer photosensitive layer having a thickness of 23 μm.
【化２４】 [Chemical formula 24]
【０１１９】〔比較例２４〕
アルミニウムシリンダー上に下記組成の感光層塗工液を
塗布・乾燥し、厚さ２３μｍの単層感光層を形成し比較
例の電子写真感光体を作製した。
[Comparative Example 24 ] A photosensitive layer coating liquid having the following composition was applied onto an aluminum cylinder and dried to form a single-layer photosensitive layer having a thickness of 23 µm, to prepare an electrophotographic photosensitive member of Comparative Example.
【０１２０】上記実施例１７〜２４および比較例１７〜
２４で得られた各感光体について上記と同様の方法で感
光体特性を測定した。結果を表１０に示す。[0120] The above Examples 17 to 24 and Comparative Examples 17 to
With respect to each of the photoconductors obtained in 24 , the photoconductor characteristics were measured by the same method as described above. The results are shown in Table 10 .
【０１２１】[0121]
【表１０】 [Table 10]
【０１２２】次に電荷輸送材料として一般式（Ｉ）で示
される化合物と一般式（ＶＩＩ）で示される化合物を併
用した場合について、実施例２５〜３２および比較例２
５〜３２により説明する。Next, Examples 25 to 32 and Comparative Example 2 in the case where the compound represented by the general formula (I) and the compound represented by the general formula (VII) were used in combination as the charge transporting material.
5 to 32 will be described.
【０１２３】〔実施例２５〕
外径７０ｍｍのアルミニウムシリンダー上に下記組成の
下引層塗工液、電荷発生層塗工液、電荷輸送層塗工液を
順次、塗布・乾燥して各々４μｍの下引層、０．２μｍ
の電荷発生層、２２μｍの電荷輸送層を形成し、本発明
の電子写真感光体を作製した。
Example 25 An undercoat layer coating solution, a charge generating layer coating solution, and a charge transporting layer coating solution having the following compositions were sequentially applied and dried on an aluminum cylinder having an outer diameter of 70 mm to obtain a coating solution of 4 μm each. Subbing layer, 0.2 μm
The charge generation layer and the charge transport layer having a thickness of 22 μm were formed to prepare the electrophotographic photoreceptor of the present invention.
【化１７】 [Chemical 17]
【０１２４】〔比較例２５〕
実施例２５の電荷輸送層塗工液を下記組成のものに変え
た以外は実施例２５と同様にして比較例の電子写真感光
体を作製した。
Comparative Example 25 An electrophotographic photosensitive member of Comparative Example was prepared in the same manner as in Example 25 , except that the coating solution for charge transport layer in Example 25 was changed to the composition shown below.
【０１２５】〔実施例２６〕
アルミニウムシリンダー表面を陽極酸化処理した後、封
孔処理を行った。この上に、下記電荷発生層塗工液、電
荷輸送層塗工液を順次塗布・乾燥して各々０．２μｍの
電荷発生層、２０μｍの電荷輸送層を形成し本発明の電
子写真感光体を作製した。
Example 26 The surface of an aluminum cylinder was anodized and then sealed. The following charge generating layer coating liquid and charge transporting layer coating liquid are successively applied and dried to form a charge generating layer of 0.2 μm and a charge transporting layer of 20 μm, respectively. It was made.
【化１８】 [Chemical 18]
【０１２６】〔比較例２６〕
実施例２６の電荷輸送層塗工液において、化合物ＮＯ．
ＶＩＩ−１５の化合物を添加しないこと以外は実施例２
６と同様にして比較例の電子写真感光体を作製した。[Comparative Example 26 ] [0126] In the charge transport layer coating liquid of Example 26 , the compound NO.
Example 2 except that no compound of VII-15 was added.
An electrophotographic photoreceptor of Comparative Example was produced in the same manner as in No. 6 .
【０１２７】〔実施例２７〕
アルミニウムシリンダー上に下記組成の下引層塗工液、
下記組成の電荷発生層塗工液、下記組成の電荷輸送層塗
工液を、順次塗布・乾燥して各々２μｍの下引層、０．
２μｍの電荷発生層、２μｍの電荷輸送層を形成し、本
発明の電子写真感光体を作製した。
Example 27 An undercoat layer coating solution having the following composition on an aluminum cylinder,
A charge generation layer coating solution having the following composition and a charge transport layer coating solution having the following composition were sequentially applied and dried to form an undercoat layer of 2 μm each.
A 2 μm charge generation layer and a 2 μm charge transport layer were formed to prepare an electrophotographic photoreceptor of the present invention.
【化１９】 [Chemical 19]
【０１２８】〔比較例２７〕
実施例２７の電荷輸送層塗工液を下記組成のものにした
以外は実施例２７と同様にして比較例の電子写真感光体
を作製した。
Comparative Example 27 An electrophotographic photoreceptor of Comparative Example was prepared in the same manner as in Example 27 except that the coating solution for charge transport layer of Example 27 had the following composition.
【０１２９】〔実施例２８〕
実施例２５の電荷輸送層塗工液を下記組成のものにした
以外は実施例２５と同様にして本発明の電子写真感光体
を作製した。
Example 28 An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 25 except that the coating solution for charge transport layer of Example 25 had the following composition.
【０１３０】〔比較例２８〕
実施例２８の電荷輸送層塗工液を下記組成のものにした
以外は実施例２８と同様にして比較例の電子写真感光体
を作製した。
Comparative Example 28 An electrophotographic photoreceptor of Comparative Example was prepared in the same manner as in Example 28 except that the coating solution for charge transport layer of Example 28 had the following composition.
【０１３１】〔実施例２９〕
実施例２６の電荷輸送層塗工液を下記組成のものにした
以外は実施例２６と同様にして本発明の電子写真感光体
を作製した。
Example 29 An electrophotographic photosensitive member of the present invention was produced in the same manner as in Example 26 , except that the coating solution for charge transport layer of Example 26 had the following composition.
【０１３２】〔比較例２９〕
実施例２９の電荷輸送層塗工液を下記組成のものにした
以外は実施例２９と同様にして比較例の電子写真感光体
を作製した。
Comparative Example 29 An electrophotographic photosensitive member of Comparative Example was prepared in the same manner as in Example 29 , except that the coating solution for charge transport layer of Example 29 had the following composition.
【０１３３】〔実施例３０〕
実施例２７の電荷輸送層塗工液を下記組成のものにした
以外は実施例２７と同様にして本発明の電子写真感光体
を作製した。
Example 30 An electrophotographic photosensitive member of the present invention was produced in the same manner as in Example 27 except that the coating solution for charge transport layer of Example 27 had the following composition.
【０１３４】〔比較例３０〕
実施例３０の電荷輸送層塗工液において、化合物ＮＯ．
Ｉ−１２の化合物を添加しないこと以外は実施例３０と
同様にして比較例の電子写真感光体を作製した。[Comparative Example 30 ] In the charge transport layer coating liquid of Example 30 , the compound NO.
An electrophotographic photoreceptor of Comparative Example was produced in the same manner as in Example 30 except that the compound of I-12 was not added.
【０１３５】〔実施例３１〕
アルミニウムシリンダー上に下記組成の共晶錯体光導電
層塗工液を塗布・乾燥し、厚さ２５μｍの共晶錯体光導
電層を形成し本発明の電子写真感光体を作製した。
Example 31 An eutectic complex photoconductive layer coating solution having the following composition was applied onto an aluminum cylinder and dried to form a eutectic complex photoconductive layer having a thickness of 25 μm. Was produced.
【０１３６】〔比較例３１〕
実施例３１の電荷輸送層塗工液において、化合物ＮＯ．
ＶＩＩ−１７の化合物を添加しないこと以外は実施例３
１と同様にして比較例の電子写真感光体を作製した。[Comparative Example 31 ] In the charge transport layer coating liquid of Example 31 , the compound NO.
Example 3 except that no compound of VII-17 was added.
An electrophotographic photoreceptor of Comparative Example was produced in the same manner as in 1 .
【０１３７】〔実施例３２〕
アルミニウムシリンダー上に下記組成の感光層塗工液を
塗布・乾燥し、厚さ２３μｍの単層感光層を形成し本発
明の電子写真感光体を作製した。
Example 32 An electrophotographic photosensitive member of the present invention was prepared by coating a photosensitive layer coating liquid having the following composition on an aluminum cylinder and drying it to form a single-layer photosensitive layer having a thickness of 23 μm.
【化２０】 [Chemical 20]
【０１３８】〔比較例３２〕
アルミニウムシリンダー上に下記組成の感光層塗工液を
塗布・乾燥し、厚さ２３μｍの単層感光層を形成し比較
例の電子写真感光体を作製した。
[Comparative Example 32 ] A photosensitive layer coating solution having the following composition was applied onto an aluminum cylinder and dried to form a single-layer photosensitive layer having a thickness of 23 μm to prepare an electrophotographic photosensitive member of Comparative Example.
【０１３９】上記実施例２５〜３２および比較例２５〜
３２で得られた各感光体について前記と同様の方法で感
光体特性を測定した。結果を表１１に示す。Examples 25 to 32 and Comparative Example 25 to
With respect to each of the photoconductors obtained in No. 32 , the photoconductor characteristics were measured by the same method as described above. The results are shown in Table 11.
【０１４０】[0140]
【表１１】 [Table 11]
【０１４１】次に電荷輸送材料として一般式（Ｉ）で示
される化合物と一般式（ＶＩＩＩ）で示される化合物を
併用した場合について、実施例３３〜４０および比較例
３３〜４０により説明する。Next, in the case where the compound represented by the general formula (I) and the compound represented by the general formula (VIII) were used in combination as the charge transport material, Examples 33 to 40 and Comparative Examples were carried out.
33 to 40 will be described.
【０１４２】〔実施例３３〕
外径７０ｍｍのアルミニウムシリンダー上に下記組成の
下引層塗工液、電荷発生層塗工液、電荷輸送層塗工液を
順次、塗布・乾燥して各々４μｍの下引層、０．２μｍ
の電荷発生層、２２μｍの電荷輸送層を形成し、本発明
の電子写真感光体を作製した。
Example 33 An undercoat layer coating solution, a charge generating layer coating solution, and a charge transporting layer coating solution having the following compositions were sequentially applied and dried on an aluminum cylinder having an outer diameter of 70 mm to obtain a coating solution of 4 μm each. Subbing layer, 0.2 μm
The charge generation layer and the charge transport layer having a thickness of 22 μm were formed to prepare the electrophotographic photoreceptor of the present invention.
【化１３】 [Chemical 13]
【０１４３】〔比較例３３〕
実施例３３の電荷輸送層塗工液を下記組成のものに変え
た以外は実施例３３と同様にして比較例の電子写真感光
体を作製した。
Comparative Example 33 An electrophotographic photosensitive member of Comparative Example was prepared in the same manner as in Example 33 except that the coating solution for the charge transport layer of Example 33 was changed to the composition shown below.
【０１４４】〔実施例３４〕
アルミニウムシリンダー表面を陽極酸化処理した後、封
孔処理を行った。この上に、下記電荷発生層塗工液、電
荷輸送層塗工液を順次塗布・乾燥して各々０．２μｍの
電荷発生層、２０μｍの電荷輸送層を形成し本発明の電
子写真感光体を作製した。
Example 34 The surface of an aluminum cylinder was anodized and then sealed. The following charge generating layer coating liquid and charge transporting layer coating liquid are successively applied and dried to form a charge generating layer of 0.2 μm and a charge transporting layer of 20 μm, respectively. It was made.
【化１４】 [Chemical 14]
【０１４５】〔比較例３４〕
実施例３４の電荷輸送層塗工液において、化合物ＮＯ．
ＶＩＩＩ−３１の化合物を添加しないこと以外は実施例
３４と同様にして比較例の電子写真感光体を作製した。[Comparative Example 34 ] In the charge transport layer coating liquid of Example 34 , the compound NO.
Example except that no compound of VIII-31 was added
An electrophotographic photoreceptor of Comparative Example was produced in the same manner as in 34 .
【０１４６】〔実施例３５〕
アルミニウムシリンダー上に下記組成の下引層塗工液、
下記組成の電荷発生層塗工液、下記組成の電荷輸送層塗
工液を、順次塗布・乾燥して各々２μｍの下引層、０．
２μｍの電荷発生層、２μｍの電荷輸送層を形成し、本
発明の電子写真感光体を作製した。
Example 35 An undercoat layer coating solution having the following composition on an aluminum cylinder,
A charge generation layer coating solution having the following composition and a charge transport layer coating solution having the following composition were sequentially applied and dried to form an undercoat layer of 2 μm each.
A 2 μm charge generation layer and a 2 μm charge transport layer were formed to prepare an electrophotographic photoreceptor of the present invention.
【化１５】 [Chemical 15]
【０１４７】〔比較例３５〕
実施例３５の電荷輸送層塗工液を下記組成のものにした
以外は実施例３５と同様にして比較例の電子写真感光体
を作製した。
Comparative Example 35 An electrophotographic photosensitive member of Comparative Example was prepared in the same manner as in Example 35 except that the coating solution for charge transport layer of Example 35 had the following composition.
【０１４８】〔実施例３６〕
実施例３３の電荷輸送層塗工液を下記組成のものにした
以外は実施例３３と同様にして本発明の電子写真感光体
を作製した。
Example 36 An electrophotographic photosensitive member of the present invention was produced in the same manner as in Example 33 except that the coating solution for the charge transport layer of Example 33 had the following composition.
【０１４９】〔比較例３６〕
実施例３６の電荷輸送層塗工液を下記組成のものにした
以外は実施例３６と同様にして比較例の電子写真感光体
を作製した。
Comparative Example 36 An electrophotographic photosensitive member of Comparative Example was prepared in the same manner as in Example 36 , except that the coating solution for charge transport layer of Example 36 had the following composition.
【０１５０】〔実施例３７〕
実施例３４の電荷輸送層塗工液を下記組成のものにした
以外は実施例３４と同様にして本発明の電子写真感光体
を作製した。
Example 37 An electrophotographic photosensitive member of the present invention was produced in the same manner as in Example 34 except that the coating solution for charge transport layer of Example 34 had the following composition.
【０１５１】〔比較例３７〕
実施例３７の電荷輸送層塗工液を下記組成のものにした
以外は実施例３７と同様にして比較例の電子写真感光体
を作製した。
Comparative Example 37 An electrophotographic photosensitive member of Comparative Example was prepared in the same manner as in Example 37 except that the coating solution for the charge transport layer of Example 37 had the following composition.
【０１５２】〔実施例３８〕
実施例３５の電荷輸送層塗工液を下記組成のものにした
以外は実施例３５と同様にして本発明の電子写真感光体
を作製した。
Example 38 An electrophotographic photosensitive member of the present invention was produced in the same manner as in Example 35 except that the coating solution for charge transport layer of Example 35 had the following composition.
【０１５３】〔比較例３８〕
実施例３８の電荷輸送層塗工液において、化合物ＮＯ．
Ｉ−７５の化合物を添加しないこと以外は実施例３８と
同様にして比較例の電子写真感光体を作製した。[Comparative Example 38 ] In the charge transport layer coating solution of Example 38 , the compound NO.
An electrophotographic photoreceptor of Comparative Example was produced in the same manner as in Example 38 except that the compound of I-75 was not added.
【０１５４】〔実施例３９〕
アルミニウムシリンダー上に下記組成の共晶錯体光導電
層塗工液を塗布・乾燥し、厚さ２５μｍの共晶錯体光導
電層を形成し本発明の電子写真感光体を作製した。
Example 39 An eutectic complex photoconductive layer coating solution having the following composition was applied onto an aluminum cylinder and dried to form a eutectic complex photoconductive layer having a thickness of 25 μm. Was produced.
【０１５５】〔比較例３９〕
実施例３９の電荷輸送層塗工液において、化合物ＮＯ．
ＶＩＩＩ−２７の化合物を添加しないこと以外は実施例
３９と同様にして比較例の電子写真感光体を作製した。[Comparative Example 39 ] In the charge transport layer coating liquid of Example 39 , the compound NO.
Example except that no compound of VIII-27 was added
An electrophotographic photoreceptor of Comparative Example was produced in the same manner as in 39 .
【０１５６】〔実施例４０〕
アルミニウムシリンダー上に下記組成の感光層塗工液を
塗布・乾燥し、厚さ２３μｍの単層感光層を形成し本発
明の電子写真感光体を作製した。
Example 40 An aluminum cylinder was coated with a photosensitive layer coating liquid having the following composition and dried to form a single-layer photosensitive layer having a thickness of 23 μm to prepare an electrophotographic photosensitive member of the present invention.
【化１６】 [Chemical 16]
【０１５７】〔比較例４０〕
アルミニウムシリンダー上に下記組成の感光層塗工液を
塗布・乾燥し、厚さ２３μｍの単層感光層を形成し比較
例の電子写真感光体を作製した。
Comparative Example 40 An aluminum cylinder was coated with a photosensitive layer coating solution having the following composition and dried to form a single-layer photosensitive layer having a thickness of 23 μm to prepare an electrophotographic photoreceptor of Comparative Example.
【０１５８】上記実施例３３〜４０および比較例３３〜
４０で得られた各感光体について前記と同様の方法で感
光体特性を測定した。結果を表１２に示す。Examples 33 to 40 and Comparative Example 33 to
With respect to each of the photoconductors obtained in No. 40 , the photoconductor characteristics were measured by the same method as described above. The results are shown in Table 12.
【０１５９】[0159]
【表１２】 [Table 12]
【０１６０】次に電荷輸送材料として一般式（Ｉ）で示
される化合物と一般式（ＩＸ）で示される化合物を併用
した場合について、実施例４１〜４８および比較例４１
〜４８により説明する。Next, in the case where the compound represented by the general formula (I) and the compound represented by the general formula (IX) were used in combination as the charge transport material, Examples 41 to 48 and Comparative Example 41 were used.
~ 48 .
【０１６１】〔実施例４１〕
外径７０ｍｍのアルミニウムシリンダー上に下記組成の
下引層塗工液、電荷発生層塗工液、電荷輸送層塗工液を
順次、塗布・乾燥して各々４μｍの下引層、０．２μｍ
の電荷発生層、２２μｍの電荷輸送層を形成し、本発明
の電子写真感光体を作製した。
Example 41 An undercoat layer coating solution, a charge generation layer coating solution, and a charge transport layer coating solution having the following compositions were sequentially applied and dried on an aluminum cylinder having an outer diameter of 70 mm to form a coating solution of 4 μm each. Subbing layer, 0.2 μm
The charge generation layer and the charge transport layer having a thickness of 22 μm were formed to prepare the electrophotographic photoreceptor of the present invention.
【化２１】 [Chemical 21]
【０１６２】〔比較例４１〕
実施例４１の電荷輸送層塗工液を下記組成のものに変え
た以外は実施例４１と同様にして比較例の電子写真感光
体を作製した。
Comparative Example 41 An electrophotographic photosensitive member of Comparative Example was prepared in the same manner as in Example 41 except that the coating solution for the charge transport layer in Example 41 was changed to the composition shown below.
【０１６３】〔実施例４２〕
アルミニウムシリンダー表面を陽極酸化処理した後、封
孔処理を行った。この上に、下記電荷発生層塗工液、電
荷輸送層塗工液を順次塗布・乾燥して各々０．２μｍの
電荷発生層、２０μｍの電荷輸送層を形成し本発明の電
子写真感光体を作製した。
Example 42 The surface of an aluminum cylinder was anodized and then sealed. The following charge generating layer coating liquid and charge transporting layer coating liquid are successively applied and dried to form a charge generating layer of 0.2 μm and a charge transporting layer of 20 μm, respectively. It was made.
【化２２】 [Chemical formula 22]
【０１６４】〔比較例４２〕
実施例４２の電荷輸送層塗工液において、化合物ＮＯ．
ＩＸ−４の化合物を添加しないこと以外は実施例４２と
同様にして比較例の電子写真感光体を作製した。[Comparative Example 42 ] In the charge transport layer coating liquid of Example 42 , the compound NO.
An electrophotographic photoreceptor of Comparative Example was produced in the same manner as in Example 42 except that the compound of IX-4 was not added.
【０１６５】〔実施例４３〕
アルミニウムシリンダー上に下記組成の下引層塗工液、
下記組成の電荷発生層塗工液、下記組成の電荷輸送層塗
工液を、順次塗布・乾燥して各々２μｍの下引層、０．
２μｍの電荷発生層、２μｍの電荷輸送層を形成し、本
発明の電子写真感光体を作製した。
Example 43 An undercoat layer coating solution having the following composition on an aluminum cylinder,
A charge generation layer coating solution having the following composition and a charge transport layer coating solution having the following composition were sequentially applied and dried to form an undercoat layer of 2 μm each.
A 2 μm charge generation layer and a 2 μm charge transport layer were formed to prepare an electrophotographic photoreceptor of the present invention.
【化２３】 [Chemical formula 23]
【０１６６】〔比較例４３〕
実施例４３の電荷輸送層塗工液を下記組成のものにした
以外は実施例４３と同様にして比較例の電子写真感光体
を作製した。
Comparative Example 43 An electrophotographic photosensitive member of Comparative Example was prepared in the same manner as in Example 43 except that the coating solution for the charge transport layer of Example 43 had the following composition.
【０１６７】〔実施例４４〕
実施例４１の電荷輸送層塗工液を下記組成のものにした
以外は実施例４１と同様にして本発明の電子写真感光体
を作製した。
Example 44 An electrophotographic photosensitive member of the present invention was produced in the same manner as in Example 41 except that the coating solution for charge transport layer of Example 41 had the following composition.
【０１６８】〔比較例４４〕
実施例４４の電荷輸送層塗工液を下記組成のものにした
以外は実施例４４と同様にして比較例の電子写真感光体
を作製した。
Comparative Example 44 An electrophotographic photoreceptor of Comparative Example was prepared in the same manner as in Example 44 except that the coating solution for charge transport layer of Example 44 had the following composition.
【０１６９】〔実施例４５〕
実施例４２の電荷輸送層塗工液を下記組成のものにした
以外は実施例４２と同様にして本発明の電子写真感光体
を作製した。
[Example 45 ] An electrophotographic photosensitive member of the present invention was produced in the same manner as in Example 42 except that the coating solution for the charge transport layer of Example 42 had the following composition.
【０１７０】〔比較例４５〕
実施例４５の電荷輸送層塗工液を下記組成のものにした
以外は実施例４５と同様にして比較例の電子写真感光体
を作製した。
Comparative Example 45 An electrophotographic photosensitive member of Comparative Example was prepared in the same manner as in Example 45 , except that the coating solution for charge transport layer of Example 45 had the following composition.
【０１７１】〔実施例４６〕
実施例４３電荷輸送層塗工液を下記組成のものにした以
外は実施例４３と同様にして本発明の電子写真感光体を
作製した。
[Example 46 ] Example 43 An electrophotographic photosensitive member of the present invention was produced in the same manner as in Example 43 except that the coating solution for the charge transport layer had the following composition.
【０１７２】〔比較例４６〕
実施例４６の電荷輸送層塗工液において、化合物ＮＯ．
Ｉ−７８の化合物を添加しないこと以外は実施例４６と
同様にして比較例の電子写真感光体を作製した。[Comparative Example 46 ] In the charge transport layer coating solution of Example 46 , the compound NO.
An electrophotographic photoreceptor of Comparative Example was produced in the same manner as in Example 46 except that the compound of I-78 was not added.
【０１７３】〔実施例４７〕
アルミニウムシリンダー上に下記組成の共晶錯体光導電
層塗工液を塗布・乾燥し、厚さ２５μｍの共晶錯体光導
電層を形成し本発明の電子写真感光体を作製した。
Example 47 An eutectic complex photoconductive layer coating composition having the following composition was applied onto an aluminum cylinder and dried to form a eutectic complex photoconductive layer having a thickness of 25 μm. Was produced.
【０１７４】〔比較例４７〕
実施例４７の電荷輸送層塗工液において、化合物ＮＯ．
ＩＸ−３６の化合物を添加しないこと以外は実施例４７
と同様にして比較例の電子写真感光体を作製した。[Comparative Example 47 ] In the charge transport layer coating solution of Example 47 , the compound NO.
Example 47 except that no compound of IX-36 was added.
An electrophotographic photoreceptor of Comparative Example was produced in the same manner as in.
【０１７５】〔実施例４８〕
アルミニウムシリンダー上に下記組成の感光層塗工液を
塗布・乾燥し、厚さ２３μｍの単層感光層を形成し本発
明の電子写真感光体を作製した。
Example 48 An electrophotographic photosensitive member of the present invention was prepared by applying a photosensitive layer coating solution having the following composition on an aluminum cylinder and drying it to form a single-layer photosensitive layer having a thickness of 23 μm.
【化２４】 [Chemical formula 24]
【０１７６】〔比較例４８〕
アルミニウムシリンダー上に下記組成の感光層塗工液を
塗布・乾燥し、厚さ２３μｍの単層感光層を形成し比較
例の電子写真感光体を作製した。
[Comparative Example 48 ] A photosensitive layer coating solution having the following composition was applied onto an aluminum cylinder and dried to form a single-layer photosensitive layer having a thickness of 23 µm to prepare an electrophotographic photosensitive member of Comparative Example.
【０１７７】上記実施例４１〜４８および比較例４１〜
４８で得られた各感光体について上記と同様の方法で感
光体特性を測定した。結果を表１３に示す。Examples 41 to 48 and Comparative Examples 41 to
With respect to each photoconductor obtained in No. 48 , the photoconductor characteristics were measured by the same method as described above. The results are shown in Table 13 .
【０１７８】[0178]
【表１３】 [Table 13]
【０１７９】[0179]
【発明の効果】以上のように、本発明によれば、感光層
に電荷輸送材料して上記特定の２種類の化合物を用いる
ことにより高感度を維持しながら繰り返し使用によって
も優れた安定性を有する電子写真感光体が得られる。As described above, according to the present invention, by using the above-mentioned two kinds of compounds as the charge transport material in the photosensitive layer, high sensitivity can be maintained and excellent stability can be obtained even after repeated use. An electrophotographic photosensitive member having the same can be obtained.
【図１】本発明か係る単層感光体の説明図である。FIG. 1 is an explanatory diagram of a single-layer photoconductor according to the present invention.
【図２】本発明か係る積層感光体の説明図である。FIG. 2 is an explanatory diagram of a laminated photoreceptor according to the present invention.
【図３】本発明か係る積層感光体の説明図である。FIG. 3 is an explanatory diagram of a laminated photoreceptor according to the present invention.
１１ 導電性支持体 １５ 単層感光層 １７ 電荷発生層 １９ 電荷輸送層 11 Conductive support 15 Single-layer photosensitive layer 17 Charge generation layer 19 Charge transport layer
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.7 識別記号 ＦＩ Ｇ０３Ｇ 5/06 ３１５ Ｇ０３Ｇ 5/06 ３１５Ａ ３１５Ｃ ３１６ ３１６Ｂ ３１９ ３１９ ３２０ ３２０ (72)発明者 増汐 淳子 東京都大田区中馬込１丁目３番６号 株 式会社リコー内 (56)参考文献 特開 昭63−213851（ＪＰ，Ａ) 特開 平７−230176（ＪＰ，Ａ) 特開 平７−168372（ＪＰ，Ａ) 特開 平７−92705（ＪＰ，Ａ) 特開 平６−75411（ＪＰ，Ａ) 特開 平４−122948（ＪＰ，Ａ) 特開 平４−118658（ＪＰ，Ａ) 特開 平３−273258（ＪＰ，Ａ) 特開 平３−259266（ＪＰ，Ａ) 特開 平３−235957（ＪＰ，Ａ) 特開 平３−7946（ＪＰ，Ａ) 特開 平２−93653（ＪＰ，Ａ) 特開 平１−150144（ＪＰ，Ａ) (58)調査した分野(Int.Cl.7，ＤＢ名) G03G 5/00 ─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. 7 Identification code FI G03G 5/06 315 G03G 5/06 315A 315C 316 316B 319 319 320 320 (72) Inventor Atsuko Masashio Nakamagome, Ota-ku, Tokyo 1 3-6, Ricoh Co., Ltd. (56) Reference JP 63-213851 (JP, A) JP 7-230176 (JP, A) JP 7-168372 (JP, A) JP JP-A-7-92705 (JP, A) JP-A-6-75411 (JP, A) JP-A-4-122948 (JP, A) JP-A-4-118658 (JP, A) JP-A-3-273258 (JP , A) JP 3-259266 (JP, A) JP 3-235957 (JP, A) JP 3-7946 (JP, A) JP 2-93653 (JP, A) JP 1-150144 (JP, A) (58) minutes surveyed (Int.Cl. 7, DB name) G03G 5/00
Claims (2)
とする電荷発生層と少なくとも下記（２）、（４）ない
し（８）で示される化合物の組から選択される一組を含
有する電荷輸送層を積層してなることを特徴とする電子
写真感光体。 （２）下記一般式（Ｉ）で示される化合物と下記一般式
（ＩＩＩ）で示される化合物 （４）下記一般式（Ｉ）で示される化合物と下記一般式
（Ｖ）で示される化合物 （５）下記一般式（Ｉ）で示される化合物と下記一般式
（ＶＩ）で示される化合物 （６）下記一般式（Ｉ）で示される化合物と下記一般式
（ＶＩＩ）で示される化合物 （７）下記一般式（Ｉ）で示される化合物と下記一般式
（ＶＩＩＩ）で示される化合物 （８）下記一般式（Ｉ）で示される化合物と下記一般式
（ＩＸ）で示される化合物 【化１】 【化３】 【化５】 【化６】 【化７】 【化８】 【化９】 【化１０】 【化１１】 【化１２】 1. A conductive support containing a charge generation layer containing a charge generation material as a main component and at least one set selected from the set of compounds represented by the following (2), (4) to (8). An electrophotographic photoreceptor comprising a laminated charge transporting layer. (2) the following compounds of general formula (I) with a compound represented by the following general formula (III) (4) compounds represented by the compound represented by the following general formula (I) and the following general formula (V) (5 ) following the compound represented by formula (I) with a compound represented by the following general formula (VI) (6) compounds represented by the compound represented by the following general formula (I) and the following general formula (VII) (7) below compounds of general formula with a compound represented by the following general formula represented by (I) (VIII) (8 ) a compound represented by the following general formula (I) and the following general formula (IX) compound embedded image represented by [Chemical 3] [Chemical 5] [Chemical 6] [Chemical 7] [Chemical 8] [Chemical 9] [Chemical 10] [Chemical 11] [Chemical 12]
料と下記（２）、（４）ないし（８）で示される化合物
の組から選択される一組を含有する単層感光層を設けて
なることを特徴とする電子写真感光体。 （２）前記一般式（Ｉ）で示される化合物と前記一般式
（ＩＩＩ）で示される化合物 （４）前記一般式（Ｉ）で示される化合物と前記一般式
（Ｖ）で示される化合物 （５）前記一般式（Ｉ）で示される化合物と前記一般式
（ＶＩ）で示される化合物 （６）前記一般式（Ｉ）で示される化合物と前記一般式
（ＶＩＩ）で示される化合物 （７）前記一般式（Ｉ）で示される化合物と前記一般式
（ＶＩＩＩ）で示される化合物 （８）前記一般式（Ｉ）で示される化合物と前記一般式
（ＩＸ）で示される化合物2. A single-layer photosensitive layer containing at least a charge-generating material and one set selected from the group consisting of compounds represented by the following (2), (4) to (8) is provided on a conductive support. An electrophotographic photosensitive member characterized in that (2) the formula wherein the compound of formula (I) the general formula (III) compound represented by (4) the formula the formula with a compound of formula (I) (V) Compound (5 ) formula (formula with a compound represented by I) (VI) compound represented by (6) the formula (wherein the compound represented by I) the general formula (VII) a compound represented by (7) the compound represented by the general formula compound represented by the compounds represented by (I) the general formula (VIII) (8) the formula with a compound represented by the general formula (I) (IX)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP26802796A JP3496085B2 (en) | 1996-09-18 | 1996-09-18 | Electrophotographic photoreceptor |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP26802796A JP3496085B2 (en) | 1996-09-18 | 1996-09-18 | Electrophotographic photoreceptor |
Related Child Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003196827A Division JP3768495B2 (en) | 2003-07-14 | 2003-07-14 | Electrophotographic photoreceptor |
| JP2003196829A Division JP3721177B2 (en) | 2003-07-14 | 2003-07-14 | Electrophotographic photoreceptor |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH1090924A JPH1090924A (en) | 1998-04-10 |
| JP3496085B2 true JP3496085B2 (en) | 2004-02-09 |
Family
ID=17452878
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP26802796A Expired - Fee Related JP3496085B2 (en) | 1996-09-18 | 1996-09-18 | Electrophotographic photoreceptor |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3496085B2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7964327B2 (en) * | 2006-06-13 | 2011-06-21 | Ricoh Company Ltd. | Electrophotographic photoreceptor and method of preparing the photoreceptor, and image forming apparatus, image forming method and process cartridge using the photoreceptor |
-
1996
- 1996-09-18 JP JP26802796A patent/JP3496085B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH1090924A (en) | 1998-04-10 |
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