JPH0585898B2 - - Google Patents
Info
- Publication number
- JPH0585898B2 JPH0585898B2 JP59183719A JP18371984A JPH0585898B2 JP H0585898 B2 JPH0585898 B2 JP H0585898B2 JP 59183719 A JP59183719 A JP 59183719A JP 18371984 A JP18371984 A JP 18371984A JP H0585898 B2 JPH0585898 B2 JP H0585898B2
- Authority
- JP
- Japan
- Prior art keywords
- charge generation
- generation layer
- formula
- charge
- photoreceptor
- 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 - Lifetime
Links
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording-members for original recording by exposure, e.g. to light, to heat or to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
- G03G5/0601—Acyclic or carbocyclic compounds
- G03G5/0609—Acyclic or carbocyclic compounds containing oxygen
- G03G5/0611—Squaric acid
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording-members for original recording by exposure, e.g. to light, to heat or to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
- G03G5/0601—Acyclic or carbocyclic compounds
- G03G5/0612—Acyclic or carbocyclic compounds containing nitrogen
- G03G5/0614—Amines
- G03G5/06142—Amines arylamine
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording-members for original recording by exposure, e.g. to light, to heat or to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
- G03G5/0601—Acyclic or carbocyclic compounds
- G03G5/0612—Acyclic or carbocyclic compounds containing nitrogen
- G03G5/0614—Amines
- G03G5/06142—Amines arylamine
- G03G5/06144—Amines arylamine diamine
- G03G5/061443—Amines arylamine diamine benzidine
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording-members for original recording by exposure, e.g. to light, to heat or to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
- G03G5/0601—Acyclic or carbocyclic compounds
- G03G5/0618—Acyclic or carbocyclic compounds containing oxygen and nitrogen
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Photoreceptors In Electrophotography (AREA)
- Light Receiving Elements (AREA)
Description
〔産業上の利用分野〕
本発明は、機能分離型電子写真用感光体に関す
る。
〔従来技術〕
従来、電子写真用の感光体として、露光により
電荷を発生する電荷発生層と、発生した電荷を輸
送する電荷輸送層とを積層した機能分離型電子写
真用感光体の開発が行われてきている。
本発明者らはこれまでに、電荷発生材料として
スクエアリン酸誘導体を用い、電荷輸送材料とし
て後述の一般式（）で示されるジアミン化合物
を用いた二層型積層感光体に関する研究を行なつ
てきた。しかしこのような、スクエアリン酸誘導
体を主成分とする電荷発生層と、一般式（）で
示されるジアミン化合物を主成分とする電荷輸送
層とを積層した感光体は、電荷発生層と電荷輸送
層の界面における電気的バリアのために感度が十
分得られず、残留電位が生じ、さらにサイクル特
性が不安定になるという欠点を有していた。
さらに塗布方法によつては、電荷発生層上に電
荷輸送層を塗布する際、電荷輸送層の塗布溶媒に
よつて電荷発生層が侵され、電荷発生層と電荷輸
送層の均一性が乱されるため、作成した感材の画
質むらを生じるという欠点があることがわかつ
た。
〔発明の目的〕
本発明の目的は、これらの欠点を改善し、高感
度でなおかつ塗布均一性の高い安定した感光体を
提供することである。
〔発明の構成〕
本発明者らは、電荷発生層中に、前記スクエア
リン酸誘導体に対して所定量の前記ジアミン化合
物を含有させることにより、上記目的が達成され
ることを見出し、本発明を完成するに至つた。
本発明は、電荷発生層の電荷発生材料として、
一般式（）
[Industrial Field of Application] The present invention relates to a functionally separated electrophotographic photoreceptor. [Prior Art] Conventionally, as a photoreceptor for electrophotography, a functionally separated type photoreceptor for electrophotography has been developed in which a charge generation layer that generates charges upon exposure and a charge transport layer that transports the generated charges are laminated. It's getting worse. The present inventors have so far conducted research on a two-layer laminated photoreceptor using a squaric acid derivative as a charge-generating material and a diamine compound represented by the general formula () described below as a charge-transporting material. Ta. However, such a photoreceptor in which a charge generation layer mainly composed of a squaric acid derivative and a charge transport layer mainly composed of a diamine compound represented by the general formula () is laminated has a charge generation layer and a charge transport layer. Due to the electrical barrier at the layer interface, sufficient sensitivity cannot be obtained, residual potential occurs, and cycle characteristics become unstable. Furthermore, depending on the coating method, when coating the charge transport layer on the charge generation layer, the charge generation layer may be attacked by the coating solvent of the charge transport layer, and the uniformity of the charge generation layer and the charge transport layer may be disturbed. It has been found that this technique has the disadvantage of causing unevenness in the image quality of the photosensitive material produced. [Object of the Invention] An object of the present invention is to improve these drawbacks and provide a stable photoreceptor with high sensitivity and high coating uniformity. [Structure of the Invention] The present inventors have discovered that the above object can be achieved by containing a predetermined amount of the diamine compound relative to the squaric acid derivative in the charge generation layer, and have accomplished the present invention. It was completed. In the present invention, as a charge generation material of a charge generation layer,
General formula ()
【化】
（式中Ｙは、水素原子、水酸基またはメチル
基、R1，R2は独立して、メチル基、エチル基、
[Chemical formula] (In the formula, Y is a hydrogen atom, a hydroxyl group, or a methyl group, and R 1 and R 2 are independently a methyl group, an ethyl group,
【式】または[expression] or
【式】
を示し、R3は水素原子、水酸基、ハロゲン原子
またはアルキル基を示す。）
で表されるスクエアリン酸誘導体を用イ、電荷輸
送層の電荷輸送材料として、一般式（）[Formula] is shown, and R 3 represents a hydrogen atom, a hydroxyl group, a halogen atom, or an alkyl group. ) A squaric acid derivative represented by the general formula () is used as the charge transport material of the charge transport layer.
以下に実施例により本発明を説明する。 実施例 １ 下記構造式 The present invention will be explained below with reference to Examples. Example 1 Structural formula below
【化】
で示されるスクエアリン酸誘導体、すなわち２，
４−ビス−（２−メチル−４−ジエチルアミノ−
フエニル）−１，３−シクロブタジエン−ジイリ
ウム−１，３−ジオレート１重量部にポリエステ
ル樹脂（デユポン製、アドヘツシブ49000）１重
量部、テトラヒドロフラン10重量部を加え、ボー
ルミルで４時間粉砕、混合した分散液中に、Ｎ，
N′−ジフエニル、Ｎ，N′−ビス−（３−メチルフ
エニル）−〔１，1′−ビフエニル〕−４，4′−ジア
ミン１重量部を溶解した塗布液を、スプレーコー
ターを用いて、アルミニウムを蒸着したポリエス
テルフイルム〔東レ製、メタルミー（登録商標）〕
上に塗布し、80℃で４時間乾燥させ、膜厚1.5μの
電荷発生層を作成した。
この電荷発生層上に、Ｎ，N′−ジフエニル−
Ｎ，N′−ビス−（３−メチルフエニル）−〔１，
1′−ビフエニル〕−４，4′−ジアミン１重量部、
ポリカーボネート樹脂〔帝人製、パンライト（登
録商標）〕１重量部、テトラヒドロフラン10重量
部からなる均一溶液をスプレーコーターを用いて
塗布し、70℃で16時間乾燥させて厚さ23μの感光
体を得た。
また比較のために上記の感光体において、電荷
発生層中に上記ジアミン化合物を添加しない以外
は全く同じ処法により作成した感光体を得た。
次に静電複写紙試験装置（川口電気製、エレク
トロスタテイツク・ペーパー・アナライザー
SP428）を用いて、−6KVのコロナ放電を施して
負帯電させた後、１秒間暗所放置し、続いてタン
グステンランプを用い、表面の照度が10ルツクス
になるように感光層に光照射を施し、その表面電
位が暗所放置後の表面電位VDの1/2になる露光量
Ｅ1/2を求めた。その結果を添付図面に示す。
添付図面は、感光体の、露光時間に対する表面
電位の変化を示しており、この図面からE1/2は次
のように求められた。Squaric acid derivatives represented by [C], i.e. 2,
4-bis-(2-methyl-4-diethylamino-
To 1 part by weight of phenyl)-1,3-cyclobutadiene-diylium-1,3-diolate, 1 part by weight of polyester resin (manufactured by Dupont, Adhesive 49000) and 10 parts by weight of tetrahydrofuran were added, and the mixture was ground and mixed in a ball mill for 4 hours to obtain a dispersion. In the liquid, N,
A coating solution containing 1 part by weight of N'-diphenyl, N,N'-bis-(3-methylphenyl)-[1,1'-biphenyl]-4,4'-diamine was applied to the aluminum using a spray coater. Polyester film deposited with [Metal Me (registered trademark), manufactured by Toray Industries]
It was coated on top and dried at 80°C for 4 hours to form a charge generation layer with a thickness of 1.5μ. On this charge generation layer, N,N'-diphenyl-
N,N'-bis-(3-methylphenyl)-[1,
1 part by weight of 1'-biphenyl]-4,4'-diamine,
A homogeneous solution consisting of 1 part by weight of polycarbonate resin [manufactured by Teijin, Panlite (registered trademark)] and 10 parts by weight of tetrahydrofuran was applied using a spray coater and dried at 70°C for 16 hours to obtain a photoreceptor with a thickness of 23 μm. Ta. For comparison, a photoreceptor was prepared using the same process as above except that the diamine compound was not added to the charge generation layer. Next, electrostatic copying paper testing equipment (Kawaguchi Electric, Electrostatic Paper Analyzer)
SP428), the photosensitive layer is negatively charged by applying corona discharge of -6KV, left in a dark place for 1 second, and then the photosensitive layer is irradiated with light using a tungsten lamp so that the surface illuminance is 10 lux. The exposure amount E1/2 was determined so that the surface potential would be 1/2 of the surface potential V D after being left in the dark. The results are shown in the attached drawings. The attached drawing shows the change in surface potential of the photoreceptor with respect to exposure time, and from this drawing E 1/2 was determined as follows.
【表】
この表から明らかなように、電荷発生層に電荷
輸送材料を添加した場合には、添加しない場合に
くらべ感度の大幅な向上が認められた。
また感光体の断面を電子顕微鏡により観察した
ところ、電荷輸送材料を電荷発生層中に添加した
場合には添加しない場合にくらべて、電荷発生層
と電荷輸送層との界面にむらのない均一な構造が
得られていることが示された。
この様に構成された感光体は、比較例のものと
比べて感度の向上、くり返し特性の安定性がはか
れ、さらに均一な画質を得ることができた。
実施例 ２〜４
実施例１において、２，４−ビス−（２−メチ
ル−４−ジエチルアミノ−フエニル）−１，３−
シクロブタジエン−ジイリウム−１，３−ジオレ
ートの代りに、下記の構造式で示されるスクエア
リン酸誘導体を用いたほかは、全く同様の操作を
行い、電子写真用感光体を作成した。いずれも、
比較例のものとくらべて、感度が高く、くり返し
特性が安定しており、均一な画質のコピーを得る
ことができた。[Table] As is clear from this table, when a charge transport material was added to the charge generation layer, the sensitivity was significantly improved compared to when it was not added. Furthermore, when the cross section of the photoreceptor was observed using an electron microscope, it was found that when a charge transport material was added to the charge generation layer, the interface between the charge generation layer and the charge transport layer was uniform and uniform, compared to when it was not added. It was shown that the structure was obtained. The photoreceptor constructed in this way had improved sensitivity and stability in repeatability compared to the comparative example, and was able to obtain more uniform image quality. Examples 2-4 In Example 1, 2,4-bis-(2-methyl-4-diethylamino-phenyl)-1,3-
An electrophotographic photoreceptor was prepared in exactly the same manner except that a squaric acid derivative represented by the following structural formula was used in place of cyclobutadiene-diylium-1,3-diolate. both,
Compared to the comparative example, the sensitivity was higher, the repeatability was more stable, and copies with uniform image quality could be obtained.
【化】[ka]
【化】[ka]
本発明によれば、感度が高く、くり返し特性が
安定しており、画質むらを生じない安定した電子
写真用感光体が提供される。
According to the present invention, there is provided a stable electrophotographic photoreceptor that has high sensitivity, stable repeatability, and does not cause unevenness in image quality.
添付図面は、感光体の、露光時間に対する表面
電位の変化を示すグラフである。
The accompanying drawing is a graph showing changes in surface potential of a photoreceptor with respect to exposure time.
Claims (1)
（） 【化】 （式中Ｙは、水素原子、水酸基またはメチル
基、R1，R2は独立して、メチル基、エチル基、
【式】または【式】 を示し、R3は水素原子、水酸基、ハロゲン原子
またはアルキル基を示す。） で表されるスクエアリン酸誘導体を用い、電荷輸
送層の電荷輸送材料として、一般式（） 【化】 （式中Ｘはメチル基またはハロゲン原子を示
す。）で表されるジアミン化合物を用いる機能分
離型電子写真用感光体において、電荷発生層中
に、前記スクエアリン酸誘導体100重量部に対し、
前記ジアミン化合物10〜100重量部を含有させた
ことを特徴とする電子写真用感光体。[Claims] 1. As a charge generation material of the charge generation layer, a compound of the general formula () [Chemical formula] (wherein Y is a hydrogen atom, a hydroxyl group or a methyl group, R 1 and R 2 independently represent a methyl group, ethyl group,
[Formula] or [Formula], and R 3 represents a hydrogen atom, a hydroxyl group, a halogen atom, or an alkyl group. ) A diamine compound represented by the general formula () [C] (wherein X represents a methyl group or a halogen atom) is used as the charge transport material of the charge transport layer. In the functionally separated electrophotographic photoreceptor, the charge generation layer contains, for 100 parts by weight of the squaric acid derivative,
An electrophotographic photoreceptor comprising 10 to 100 parts by weight of the diamine compound.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59183719A JPS6162038A (en) | 1984-09-04 | 1984-09-04 | Electrophotografic sensitive body |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59183719A JPS6162038A (en) | 1984-09-04 | 1984-09-04 | Electrophotografic sensitive body |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6162038A JPS6162038A (en) | 1986-03-29 |
| JPH0585898B2 true JPH0585898B2 (en) | 1993-12-09 |
Family
ID=16140757
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59183719A Granted JPS6162038A (en) | 1984-09-04 | 1984-09-04 | Electrophotografic sensitive body |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6162038A (en) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2569519B2 (en) * | 1987-01-09 | 1997-01-08 | 富士ゼロックス株式会社 | Electrophotographic photoreceptor |
| JPH01261653A (en) * | 1988-04-12 | 1989-10-18 | Konica Corp | Electrophotographic sensitive body |
| JP2518974B2 (en) * | 1991-03-29 | 1996-07-31 | 三田工業株式会社 | Benzidine derivative and photoconductor using the same |
| US6376694B1 (en) | 1998-07-09 | 2002-04-23 | Chisso Corporation | Silole derivatives and organic electroluminescent element containing the same |
| US6042980A (en) * | 1998-07-21 | 2000-03-28 | Lexmark Internatonal, Inc. | Photoconductor with charge generation binder blend |
| US6902832B2 (en) | 2000-07-07 | 2005-06-07 | Chisso Corporation | Charge-transporting material containing diazapentacene derivative, luminescent material, and organic electroluminescent element employing these |
| US6617053B2 (en) | 2000-08-04 | 2003-09-09 | Chisso Corporation | Organic electroluminescent device containing dithiafulvene derivative |
| EP1186605B1 (en) | 2000-09-07 | 2003-04-16 | Chisso Corporation | Organic electroluminescent device comprising dipyridylthiophene derivative |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57144558A (en) * | 1981-03-02 | 1982-09-07 | Fuji Xerox Co Ltd | Electrophotographic receptor |
| US4521621A (en) * | 1983-12-05 | 1985-06-04 | Xerox Corporation | Novel squarine systems |
-
1984
- 1984-09-04 JP JP59183719A patent/JPS6162038A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6162038A (en) | 1986-03-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2990307B2 (en) | Electrophotographic photoreceptor | |
| JPH0585898B2 (en) | ||
| JPH07168377A (en) | Electrophotographic photoreceptor | |
| JP2823885B2 (en) | Function-separated organic electrophotographic photoreceptor | |
| JPH0221576B2 (en) | ||
| JPH04119360A (en) | Electrophotographic sensitive body | |
| JPS6313179B2 (en) | ||
| JPH03216662A (en) | Electrophotographic sensitive body | |
| JPS5936255A (en) | Electrophotographic photoreceptor | |
| KR940001485B1 (en) | Organic laminated electrophotographic photosensitive member and manufacturing method thereof | |
| JPH07160022A (en) | Electrophotographic photoreceptor | |
| JPH0456866A (en) | Electrophotographic photosensitive body | |
| JP2834101B2 (en) | Electrophotographic photoreceptor and electrophotographic apparatus | |
| JPH04172360A (en) | Electrophotographic sensitive body | |
| JPH0815879A (en) | Electrophotographic photoreceptor | |
| JP3094603B2 (en) | Electrophotographic photoreceptor | |
| JPH0213963A (en) | Electrophotographic sensitive body | |
| JPH043169A (en) | Electrophotographic sensitive body | |
| JPH01314248A (en) | Electrophotographic sensitive body | |
| JPH03282555A (en) | Electrophotographic sensitive body | |
| JPH01314251A (en) | Electrophotographic sensitive body | |
| JPH0756368A (en) | Electrophotographic photoconductor | |
| JPH06230592A (en) | Electrophotogtaphic sensitive body | |
| JPH03109555A (en) | Electrophotographic sensitive body | |
| JPH01152464A (en) | Electrophotographic sensitive body |