JPS63158559A - Electrophotographic sensitive body - Google Patents

Electrophotographic sensitive body

Info

Publication number
JPS63158559A
JPS63158559A JP30687886A JP30687886A JPS63158559A JP S63158559 A JPS63158559 A JP S63158559A JP 30687886 A JP30687886 A JP 30687886A JP 30687886 A JP30687886 A JP 30687886A JP S63158559 A JPS63158559 A JP S63158559A
Authority
JP
Japan
Prior art keywords
group
charge
photoreceptor
layer
weight
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
JP30687886A
Other languages
Japanese (ja)
Inventor
Masami Kuroda
昌美 黒田
Yoichi Nakamura
洋一 中村
Noboru Kosho
古庄 昇
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Fuji Electric Co Ltd
Original Assignee
Fuji Electric Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Fuji Electric Co Ltd filed Critical Fuji Electric Co Ltd
Priority to JP30687886A priority Critical patent/JPS63158559A/en
Publication of JPS63158559A publication Critical patent/JPS63158559A/en
Pending legal-status Critical Current

Links

Classifications

    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03GELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02Charge-receiving layers
    • G03G5/04Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0622Heterocyclic compounds
    • G03G5/0644Heterocyclic compounds containing two or more hetero rings
    • G03G5/0661Heterocyclic compounds containing two or more hetero rings in different ring systems, each system containing at least one hetero ring

Landscapes

  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Photoreceptors In Electrophotography (AREA)

Abstract

PURPOSE:To obtain a photosensitive body high in sensitivity and superior in characteristics resisting to repeated uses by incorporating a specified ethylenic compound in a photosensitive layer as an electric charge transfer material. CONSTITUTION:The photosensitive layer formed on an electric conductive substrate contains at least one of the ethylenic compounds represented by formula I in which each of n and m is an integer of 0-5; each of R1-R14 is H, halogen, OH, alkyl, alkoxy, allyl, carboxy, ester, aryl, cyano, nitro, amino, alkylamino, or arylamino; and R15-R16 is H, lower alkyl, or aryl, thus permitting the obtained photosensitive body to be high in sensitivity even in the case of positive and negative charging, and superior in repeated use characteristics.

Description

【発明の詳細な説明】 〔産業上の利用分野〕 本発明は電子写真用感光体に関し、詳しくは導電性基体
上に形成せしめた感光層の中に、前記一般式(I)で示
されるエチレン化合物を含有する事を特徴とする電子写
真用感光体に関する。
DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to an electrophotographic photoreceptor, and more specifically, the present invention relates to an electrophotographic photoreceptor, and more specifically, an ethylene compound represented by the general formula (I) is contained in a photosensitive layer formed on a conductive substrate. The present invention relates to an electrophotographic photoreceptor characterized by containing a compound.

〔従来の技術〕[Conventional technology]

従来より電子写真用感光体く以下感光体とも称する)の
感光材料としてはセレンまたはセレン合金などの無機光
導電性物質、酸化亜鉛あるいは硫化カドミウムなどの無
機光導電性物質を樹脂結着剤中に分散させたもの、ポI
JN−ビニールカルバゾールまたはポリビニールアント
ラセンなどの有機光導電性物質、フタロシアニン化合物
あるいはビスアゾ化合物などの有機光導電性物質または
、これら光導電性物質を樹脂納置中に分散させたものな
どが利用されている。
Conventionally, photosensitive materials for electrophotographic photoreceptors (hereinafter also referred to as photoreceptors) have been made using inorganic photoconductive substances such as selenium or selenium alloys, or inorganic photoconductive substances such as zinc oxide or cadmium sulfide in a resin binder. Dispersed, Po I
Organic photoconductive substances such as JN-vinyl carbazole or polyvinyl anthracene, organic photoconductive substances such as phthalocyanine compounds or bisazo compounds, or these photoconductive substances dispersed in resin are used. There is.

また感光体には暗所で表面電荷を保持する機能、光を受
容して電荷を発生する機能、同じく光を受容して電荷を
輸送する機能とが必要であるが、一つの層でこれらの機
能をあわ仕もったいわゆる単層型感光体と、主として電
荷発生に寄与する層と暗所での表面電荷と光受容時の電
荷輸送に寄与する層とに機能分離した層を積層したいわ
ゆる積層型感光体がある。これらの感光体を用いた電子
写真法による画像形成には、例えばカールソン方式が適
用される。゛この方式での画像形成は暗所での感光体へ
のコロナ放電による帯電、帯電された感光体表面上への
原稿の文字や絵などの静電潜像の形成、形成された静電
潜像のトナーによる現像、現像されたトナー像の紙など
の支持体への定着により行われ、トナー像転写後の感光
体は除電、残留トナーの除去、光除電などを行った後、
再使用に供される。
In addition, a photoreceptor must have the function of retaining surface charge in the dark, the function of receiving light and generating charge, and the function of receiving light and transporting charge, but these functions can be achieved in one layer. A so-called multi-layered photoreceptor is a so-called single-layer type photoreceptor with multiple functions, and a laminated layer with functionally separated layers: a layer that mainly contributes to charge generation, a layer that contributes to surface charge in the dark, and a layer that contributes to charge transport during light reception. There is a type photoreceptor. For example, the Carlson method is applied to image formation by electrophotography using these photoreceptors.゛Image formation using this method involves charging the photoconductor in a dark place by corona discharge, forming an electrostatic latent image of the original text or picture on the surface of the charged photoconductor, and This is done by developing the image with toner and fixing the developed toner image on a support such as paper, and after the toner image has been transferred, the photoreceptor is subjected to static neutralization, removal of residual toner, photostatic static elimination, etc.
Subject to reuse.

近年、可とう性、熱安定性、膜形成性などの利点により
、有機材料を用いた電子写真用感光体が実用化されてき
ている。例えば、ポリ−N−ビニールカルバゾールと2
.4.1−zニトロフルオレン−9−オンとからなる感
光体(米国特許第3484237号明細書に記載)、有
機顔料を主成分とする感光体く特開昭47−37543
号公報に記載)、染料と樹脂とからなる共晶錯体を主成
分とする感光体(特開昭47−10735号公報に記載
)などである。
In recent years, electrophotographic photoreceptors using organic materials have been put into practical use due to their advantages such as flexibility, thermal stability, and film-forming properties. For example, poly-N-vinyl carbazole and 2
.. 4. Photoreceptor consisting of 1-z nitrofluoren-9-one (described in U.S. Pat. No. 3,484,237), photoreceptor containing organic pigment as a main component JP-A-47-37543
(described in Japanese Unexamined Patent Publication No. 10735/1983), and a photoreceptor whose main component is a eutectic complex consisting of a dye and a resin (described in Japanese Patent Application Laid-Open No. 10735/1983).

さらに、新規ヒドラゾン化合物も数多く実用化されてい
る。
Furthermore, many new hydrazone compounds have also been put into practical use.

〔発明が解決しようとする問題点〕[Problem that the invention seeks to solve]

しかしながら、有機材料は無機材料にない多くの長所を
持つが、電子写真用感光体に要求されるすべての特性を
充分に満足するものはまだ得られていないのが現状であ
り、特に光感度および繰り返し連続使用時の特性に問題
があった。
However, although organic materials have many advantages that inorganic materials do not have, it is currently not possible to obtain a material that satisfactorily satisfies all the characteristics required of an electrophotographic photoreceptor, especially in terms of photosensitivity and There were problems with the characteristics when used repeatedly and continuously.

本発明は、上述の点に鑑みてなされたものであって、感
光層に電荷輸送性物質として今まで用いられたことのな
い新しい有機材料を用いることにより、高感度で繰り返
し特性の優れた複写機用およびプリンタ用の電子写真用
感光体を提供することを目的とする。
The present invention has been made in view of the above points, and by using a new organic material that has never been used as a charge transporting substance in the photosensitive layer, copying with high sensitivity and excellent repeatability can be achieved. The purpose of the present invention is to provide electrophotographic photoreceptors for machines and printers.

〔問題点を解決するための手段〕[Means for solving problems]

上記目的を達成するために、本発明によれば、下記一般
式(I)で示されるエチレン化合物のうちの少なくとも
一種類を含む感光層を有する電子写真用感光体とする。
In order to achieve the above object, the present invention provides an electrophotographic photoreceptor having a photosensitive layer containing at least one type of ethylene compound represented by the following general formula (I).

(式(I)中、n、mはそれぞれ0〜5の整数、R3−
R1はそれぞれ水素原子、ハロゲン原子、ヒドロキン基
、アルキル基、アルコキシ基、アリル基。
(In formula (I), n and m are each integers of 0 to 5, R3-
R1 is a hydrogen atom, a halogen atom, a hydroquine group, an alkyl group, an alkoxy group, or an allyl group, respectively.

カルボキンル基、エステル基、アリール基、シアノ基、
ニトロ基、アミノ基、アルキルアミノ基。
Carboquine group, ester group, aryl group, cyano group,
Nitro group, amino group, alkylamino group.

またはアリールアミノ基を表す。RIS、 R16は水
素原子、低級アルキル基、またはアリール基を表す。) 〔作用〕 本発明に用いられる前記一般式(I)のエチレン化合物
は、その合成法については文献に述べられている。しか
しながら、これらエチレン化合物を感光層に用いた例は
知られていない。本発明者らは、前記目的を達成するた
めに各種有機材料について鋭意検討を進めるなかで、こ
れらエチレン化合物について数多くの実験を行った結果
、その技術的解明はまだ充分なされてはいないが、この
よ11前記一般式(I)で示されるエチレン化合物を電
荷輸送性物質として感光層に用いることにより、高感度
で繰り返し特性の優れた感光体が得られることを見出し
たのである。
Or represents an arylamino group. RIS, R16 represents a hydrogen atom, a lower alkyl group, or an aryl group. ) [Function] The synthesis method of the ethylene compound of the general formula (I) used in the present invention is described in the literature. However, there are no known examples of using these ethylene compounds in photosensitive layers. In order to achieve the above objective, the present inventors conducted numerous experiments on these ethylene compounds while conducting intensive studies on various organic materials. It has been discovered that by using the ethylene compound represented by the general formula (I) in the photosensitive layer as a charge transporting substance, a photoreceptor with high sensitivity and excellent repeatability can be obtained.

〔実施例〕〔Example〕

本発明に用いる前記一般式(I)で表されるエチレン化
合物の具体例を例示すると次の通りである。
Specific examples of the ethylene compound represented by the general formula (I) used in the present invention are as follows.

化合物 化合物 化合物Nα23 Nα24 No、25 No、26 No、27 No、28 化合物Nα29 Nα3O Nα31 Nα32 Nα34 本発明の感光体は前述のエチレン化合物を感光層中に含
有させたものであるが、これらエチレン化合物の応用の
仕方によって、第1図、第2図、あるいは第3図に示し
たごとくに用いることができる。
Compound Compound Compound Nα23 Nα24 No, 25 No, 26 No, 27 No, 28 Compound Nα29 Nα3O Nα31 Nα32 Nα34 The photoreceptor of the present invention contains the above-mentioned ethylene compound in the photosensitive layer. Depending on the application, it can be used as shown in FIG. 1, FIG. 2, or FIG. 3.

第1図〜第3図は本発明の感光体のそれぞれ異なる実施
例の概念的断面図、1は導電性基体、20゜21、22
は感光層、3は電荷発生質、4は電荷発生層、5は電荷
輸送性物質、6は電荷輸送層、7は被覆層である。
1 to 3 are conceptual cross-sectional views of different embodiments of the photoreceptor of the present invention, 1 is a conductive substrate, 20° 21, 22
3 is a photosensitive layer, 3 is a charge-generating material, 4 is a charge-generating layer, 5 is a charge-transporting material, 6 is a charge-transporting layer, and 7 is a coating layer.

第1図は、導電性基体l上に電荷発生物質3と電荷輸送
性物質5であるエチレン化合物を枝(脂バインダー結着
剤中に分散した感光層20(通常単層型感光体と称せら
れる構成)が設けられたものである。
FIG. 1 shows a photosensitive layer 20 (usually called a single-layer photoreceptor) in which a charge-generating substance 3 and an ethylene compound as a charge-transporting substance 5 are dispersed in a fat binder binder on a conductive substrate l. configuration) is provided.

第2図は、導電性基体1上に電荷発生物質3を主体とす
る電荷発生層4と、電荷輸送性物質5であるエチレン化
合物を含有する電荷輸送層6との積層からなる感光層2
1(通常積層型感光体と称せられる構成)が設けられた
ものである。
FIG. 2 shows a photosensitive layer 2 formed by laminating a charge generation layer 4 mainly containing a charge generation substance 3 and a charge transport layer 6 containing an ethylene compound as a charge transport substance 5 on a conductive substrate 1.
1 (a configuration commonly referred to as a laminated photoreceptor).

第3図は、第2図の逆の層構成のものである。FIG. 3 shows an inverse layer configuration to that in FIG.

この場合、電荷発生層4を保護するために被覆層7が設
けられるのが一般的である。
In this case, a covering layer 7 is generally provided to protect the charge generation layer 4.

第2図および第3図に示す二種類の1構成とする理由と
して、感光体は正帯電方式または負帯電方式で用いられ
るが、負帯電方式として第2図の層構成が通常用いられ
る。第2図の層構成で正帯電方式で用いようとしても、
これに適合する電荷輸送性物質が見つかっていないのが
現状であり、したがって、正帯電方式の感光体として本
発明者らがすでに提案したように、第3図に示す層構成
が有効なものとして挙げられるのである。
The reason for the two types of configurations shown in FIGS. 2 and 3 is that the photoreceptor is used in a positive charging system or a negative charging system, and the layer configuration shown in FIG. 2 is usually used in the negative charging system. Even if you try to use the positive charging method with the layer configuration shown in Figure 2,
At present, no charge-transporting substance has been found that meets this requirement. Therefore, as the present inventors have already proposed, the layer structure shown in Figure 3 is considered to be effective as a positive charging type photoreceptor. It can be mentioned.

第1図の感光体は、電荷発生物質を電荷輸送性物質およ
び樹脂バインダーを溶解した溶液中に分散せしめ、この
分散液を導電性基体上に塗布することによって作製でき
る。
The photoreceptor shown in FIG. 1 can be produced by dispersing a charge generating substance in a solution containing a charge transporting substance and a resin binder, and applying this dispersion onto a conductive substrate.

第2図の感光体は、導電性基体上に電荷発生物質を真空
蒸着するか、あるいは電荷発生物質の粒子を溶剤または
樹脂バインダー中に分散して得た分散液を塗布、乾燥し
、その上に電荷輸送物質および樹脂バインダーを溶解し
た溶液を塗布、乾燥することにより作製できる。
The photoreceptor shown in Figure 2 is produced by vacuum-depositing a charge-generating substance on a conductive substrate, or by coating and drying a dispersion obtained by dispersing particles of a charge-generating substance in a solvent or resin binder, and then It can be produced by applying a solution containing a charge transporting substance and a resin binder to the surface of the substrate and drying the solution.

第3図の感光体は、電荷輸送性物質および樹脂バインダ
ーを溶解した溶液を導電性基体上に塗布、乾燥し、その
上に電荷発生物質を真空蒸着するか、あるいは電荷発生
物質の粒子を溶剤または樹脂バインダー中に分散して得
た分散液を塗布、乾燥することにより作製できる。
The photoreceptor shown in Figure 3 is produced by coating a conductive substrate with a solution containing a charge-transporting substance and a resin binder and drying it, and then vacuum-depositing a charge-generating substance thereon, or by depositing particles of the charge-generating substance in a solvent. Alternatively, it can be produced by coating and drying a dispersion obtained by dispersing in a resin binder.

導電性基体1は感光体の電極としての役目と同時に他の
各層の支持体となっており、円筒状、板状、フィルム状
のいずれでも良く、材質的にはアルミニウム、ステンレ
ス鋼、ニッケルなどの金属、あるいはガラス、樹脂など
の上に導電処理をほどこしたものでも良い。
The conductive substrate 1 serves as an electrode for the photoreceptor and at the same time serves as a support for the other layers, and may be cylindrical, plate-shaped, or film-shaped, and may be made of aluminum, stainless steel, nickel, etc. It may also be made of metal, glass, resin, or the like, which has been subjected to conductive treatment.

電荷発生層4は、前記したように電荷発生物質3の粒子
を樹脂バインダー中に分散させた材料を塗布するか、あ
るいは、真空蒸着などの方法により形成され、光を受容
して電荷を発生する。また、その電荷発生効率が高いこ
とと同時に発生した電荷の電荷輸送層6および被覆層7
への注入性が重要で、電場依存性が少なく低電場でも注
入の良いことが望ましい。電荷発生物質としては、無金
属フタロシアニン、チタニルフタロシアニンなどのフタ
ロシアニン化合物、各種アゾ、キノン、インジゴ顔料あ
るいは、セレンまたはセレン化合物などが用いられ、画
像形成に使用される露光光源の光波長領域に応じて好適
な物質を選ぶことができる。電荷発生層は電荷発生機能
を有すればよいので、その膜厚は電荷発生物質の光吸収
係数より決まり一般的には5μm以下であり、好適には
1μm以下である。電荷発生層は電荷発生物質を主体と
してこれに電荷輸送性物質などを添加して使用すること
も可能である。樹脂バインダーとしては、ポリカーボネ
ート、ポリエステル、ポリアミド、ポリウレタン、エポ
キシ、シリコン樹脂、メタクリル酸エステルの重合体お
よび共重合体などを適宜組み合わせして使用することが
可能である。
The charge generation layer 4 is formed by applying a material in which particles of the charge generation substance 3 are dispersed in a resin binder as described above, or by a method such as vacuum deposition, and generates charges by receiving light. . In addition, the charge transport layer 6 and the coating layer 7 for the generated charges at the same time have a high charge generation efficiency.
It is important to have good injection properties even in low electric fields with little dependence on electric fields. As the charge generating substance, phthalocyanine compounds such as metal-free phthalocyanine and titanyl phthalocyanine, various azo, quinone, and indigo pigments, or selenium or selenium compounds are used, depending on the light wavelength range of the exposure light source used for image formation. A suitable material can be selected. Since the charge generation layer only needs to have a charge generation function, its thickness is determined by the light absorption coefficient of the charge generation substance and is generally 5 μm or less, preferably 1 μm or less. The charge generation layer is mainly composed of a charge generation substance, and a charge transporting substance can also be added thereto. As the resin binder, polycarbonate, polyester, polyamide, polyurethane, epoxy, silicone resin, polymers and copolymers of methacrylic acid ester, etc. can be used in appropriate combinations.

電荷輸送層6は樹脂バインダー中に有機電荷輸送性物質
として前記一般式(I)で示されるエチレン化合物を分
散させた塗膜であり、暗所では絶縁体層として感光体の
電荷を保持し、光受容時には電荷発生層から注入される
電荷を輸送する機能を発揮する。樹脂バインダーとして
は、ポリカーボネート、ポリエステル、ポリアミド、ポ
リウレタン、エポキシ、シリコン樹脂、メタクリル酸エ
ステルの重合体および共重合第などを用いることができ
る。
The charge transport layer 6 is a coating film in which an ethylene compound represented by the general formula (I) as an organic charge transport substance is dispersed in a resin binder, and serves as an insulating layer in the dark to retain the charge on the photoreceptor. During light reception, it functions to transport charges injected from the charge generation layer. As the resin binder, polycarbonate, polyester, polyamide, polyurethane, epoxy, silicone resin, methacrylic acid ester polymers and copolymers, etc. can be used.

被覆層7は暗所ではコロナ放電の電荷を受容して保持す
る機能を有しており、かつ電荷発生層が感応する光を透
過する性能を有し、露光時に光を透過し、電荷発生層に
到達させ、発生した電荷の注入を受けて表面電荷を中和
消滅されることが必要である。被覆材料としては、ポリ
エステル、ポリアミドなどの有機絶縁性皮膜形成材料が
適用できる。また、これら有機材料とガラス樹脂、Si
O□などの無機材料さらには金属、金属酸化物などの電
気抵抗を低減せしめる材料とを混合して用いることもで
きる。被覆材料としては有機絶縁性皮膜形成材料に限定
されることはな(Si02などの無機材料さらには金属
、金属酸化物などを蒸着、スパッタリングなどの方法に
より形成することも可能である。被覆材料は前述の通り
電荷発生物質の光の吸収極大の波長領域においてできる
だけ透明であることが望ましい。
The coating layer 7 has the function of receiving and retaining the charge of corona discharge in a dark place, and has the ability to transmit the light to which the charge generation layer is sensitive, and transmits the light upon exposure, and the charge generation layer It is necessary for the surface charge to be neutralized and annihilated by the injection of the generated charge. As the coating material, organic insulating film-forming materials such as polyester and polyamide can be used. In addition, these organic materials, glass resin, Si
It is also possible to use a mixture of inorganic materials such as O□ and materials that reduce electrical resistance such as metals and metal oxides. The coating material is not limited to organic insulating film forming materials (inorganic materials such as Si02, metals, metal oxides, etc. can also be formed by methods such as vapor deposition and sputtering.The coating material is As described above, it is desirable that the charge generating material be as transparent as possible in the wavelength region where the light absorption is maximum.

被覆層自体の膜厚は被覆層の配合組成にも依存するが、
繰り返し連続使用したとき残留電位が増大するなどの悪
影響が出ない範囲で任意に設定できる。
The thickness of the coating layer itself depends on the composition of the coating layer, but
It can be set arbitrarily within a range that does not cause adverse effects such as an increase in residual potential when used repeatedly and continuously.

以下、本発明の具体的な実施例について説明する。Hereinafter, specific examples of the present invention will be described.

実施例1 ボールミルで150時間粉砕した無金属フタロシアニン
(東京化成製)50重量部と前記化合物No、 1で示
されるエチレン化合物100重量部をポリエステル樹脂
(バイロン:東洋紡製)100重量部とテトラヒドロフ
ラン(THF)溶剤とともに3時間混合機により混練し
て塗布液を調整し、導電性基体であるアルミ蒸着ポリエ
ステルフィルム(^β−PET)上に、ワイヤーバー法
にて塗布して、乾燥後の膜厚が15μmになるように感
光層を形成して感光体を作製した。
Example 1 50 parts by weight of metal-free phthalocyanine (manufactured by Tokyo Kasei Co., Ltd.) ground for 150 hours in a ball mill and 100 parts by weight of the ethylene compound represented by Compound No. ) A coating solution was prepared by kneading it with a solvent in a mixer for 3 hours, and it was applied onto a conductive substrate, aluminum-deposited polyester film (^β-PET), using a wire bar method, and the film thickness after drying was determined. A photoreceptor was prepared by forming a photosensitive layer to have a thickness of 15 μm.

実施例2 まず、α型無金属フタロシアニンを出発原料とし、2つ
のリニアモーターを対向して配置した間にα型無金属フ
タロンアニンと作用小片としてテフロンピースを内蔵し
た非磁性縮体をおいて粉砕するL I MMA C(L
inear 1ndction Motor M+x−
ing and Crashing :富士電機製)処
理を20分間行い微粉末化した。この微粉末化された試
料1重量部とDMF (N、N−ジメチルホルムアミド
)溶剤50重量部とを超音波分散処理を行った。その後
、試料とD M Fとを分離濾過し、乾燥して無金嘱フ
タロシアニンの処理を行った。
Example 2 First, α-type metal-free phthalocyanine is used as a starting material, and while two linear motors are placed facing each other, α-type metal-free phthalocyanine and a non-magnetic condensed body containing a Teflon piece as a working piece are placed and pulverized. L I MMA C(L
inear 1ndction Motor M+x-
ing and crushing (manufactured by Fuji Electric) for 20 minutes to form a fine powder. 1 part by weight of this finely powdered sample and 50 parts by weight of DMF (N,N-dimethylformamide) solvent were subjected to ultrasonic dispersion treatment. Thereafter, the sample and DMF were separated and filtered, dried, and processed into gold-free phthalocyanine.

次に、前記化合物No、 1で示されるエチレン化合物
100重量部をテトラヒドロフラン(TH’F)700
リ !置部に溶かした液とポリメタタル酸メチルポリマー(
PMMA:東京化成)100重量部をトルエン700重
量部に溶かした液とを混合してできた塗液をアルミ蒸着
ポリエステルフィルム基体上にワイヤーバーにて塗布し
、乾燥後の膜厚が15μmになるように電荷輸送層を形
成した。このようにして得られた電荷輸送層上に上記の
処理をされた無金属フタロシアニン50重量部、ポリエ
ステル樹脂(商品名バイロン200:東洋紡製)50重
量部、PMMA50重量部とTHF溶剤とともに3時間
混合機により混練して塗布液を調整し、ワイヤーバーに
て塗布し、乾燥後の膜厚が1μmになるように電荷発生
層を形成し感光体を作製した。
Next, 100 parts by weight of the ethylene compound represented by Compound No. 1 was added to 700 parts by weight of tetrahydrofuran (TH'F).
Ri! The solution and polymethyl metatalate polymer (
A coating solution prepared by mixing 100 parts by weight of PMMA (Tokyo Kasei) dissolved in 700 parts by weight of toluene is applied onto an aluminum-deposited polyester film substrate using a wire bar, and the film thickness after drying becomes 15 μm. A charge transport layer was formed in this manner. On the thus obtained charge transport layer, 50 parts by weight of the above-treated metal-free phthalocyanine, 50 parts by weight of polyester resin (trade name: Vylon 200, manufactured by Toyobo Co., Ltd.), 50 parts by weight of PMMA and THF solvent were mixed for 3 hours. A coating solution was prepared by kneading with a machine, and applied with a wire bar to form a charge generation layer such that the film thickness after drying was 1 μm, thereby producing a photoreceptor.

実施例3 実施例1の感光層の組成を、無金属フタロシアニン50
重量部、化合物N(L 1で示されるエチレン化合物1
00重量部、ポリエステル樹脂(商品名バイロン200
:東洋紡製)50重量部、PMMA50重量部とに変更
して実施例1と同様に感光層を形成し感光体を作製した
Example 3 The composition of the photosensitive layer of Example 1 was changed to 50% metal-free phthalocyanine.
Parts by weight, compound N (ethylene compound 1 represented by L 1
00 parts by weight, polyester resin (trade name Byron 200
: manufactured by Toyobo) and 50 parts by weight of PMMA, a photosensitive layer was formed in the same manner as in Example 1, and a photoreceptor was produced.

実施例4 実施例3において、無金属フタロシアニンに変えて例え
ば特開昭47−37543に示されるようなビスアゾ顔
料であるクロログイアンブル−を用い実施例1と同様に
感光層を形成し感光体を作製した。
Example 4 In Example 3, a photosensitive layer was formed in the same manner as in Example 1 using chlorodiambre, which is a bisazo pigment as disclosed in JP-A-47-37543, instead of metal-free phthalocyanine, and a photoreceptor was formed. Created.

このようにして得られた感光体の電子写真特性を川口電
機製静電記録紙試験装置r S P−428Jを用いて
測定した。
The electrophotographic properties of the photoreceptor thus obtained were measured using an electrostatic recording paper tester RSP-428J manufactured by Kawaguchi Electric.

感光体の表面電位VS (ボルト)は暗所で+6.0k
Vのコロナ放電を10秒間行って感光体表面を正帯電せ
しめたときの初期の表面電位であり、続いてコロナ放電
を中止した状態で2秒間暗所保持したときの表面電位V
バボルト)を測定し、さらに続いて感光体表面に照度2
ルツクスの白色光を照射してV−が半分になるまでの時
間(秒)を求め半減衰露光fiE+/*(ルックス・秒
)とした。また、照度2ルツクスの白色光を10秒間照
射したときの表面電位を残留電位V、(ボルト)とした
。また、フタロシアニン化合物を電荷発生物質とした場
合、長波長光での高感度が期待できるので、波長780
nmの単色光をもちいたときの電子写真特性も同時に測
定した。すなわち、Vd までは同様に測定し、次に白
色光の替わりに1μWの単色光(7800m)を照射し
て半減衰露光量(μJ/am)を求め、また、この光を
10秒間感光体表面に照射したときの残留電位V、(ボ
ルト)を測定した。測定結果を第1表に示す。
The surface potential VS (volts) of the photoreceptor is +6.0k in the dark.
This is the initial surface potential when corona discharge of V is performed for 10 seconds to positively charge the surface of the photoreceptor, and then the surface potential is V when held in the dark for 2 seconds with corona discharge stopped.
Babolt), and then the illuminance 2 on the surface of the photoreceptor.
The time (seconds) required for V- to be halved after irradiation with lux white light was determined and was defined as half-attenuation exposure fiE+/* (lux seconds). Further, the surface potential when white light with an illuminance of 2 lux was irradiated for 10 seconds was defined as the residual potential V (volt). In addition, when a phthalocyanine compound is used as a charge generating substance, high sensitivity with long wavelength light can be expected.
At the same time, electrophotographic properties were measured using monochromatic light of nm wavelength. That is, measurements are made in the same manner up to Vd, then 1 μW monochromatic light (7800 m) is irradiated instead of white light to determine the half-attenuation exposure amount (μJ/am), and this light is applied to the photoreceptor surface for 10 seconds. The residual potential V, (volt) was measured when irradiated with . The measurement results are shown in Table 1.

第  1  表 第1表に見られるように、実施例1.2.3.4は半減
衰露光量、残留電位ともに良好であった。
Table 1 As seen in Table 1, Examples 1.2.3.4 had good half-attenuation exposure and residual potential.

実施例5 厚さ500μmのアルミニウム板上に、セレンを厚さ1
.5μmに真空蒸着し電荷発生層を形成し、次に、化合
物に2で示されるエチレン化合物100重量部をテトラ
ヒドロフラン(THF)7圓重景部に溶かした液とポリ
メタク莱し酸メチルポリマー(PMMA:東京化成)1
00重量部をトルエン700重量部に溶かした液とを混
合してできた塗液をワイヤーバーにて塗布し、乾燥後の
膜厚が20μmになるように電荷輸送層を形成した。こ
の感光体に−6,OkVのコロナ帯電を0.2秒間行い
、実施例4に準じて特性ヲ?1lll 定L タト、:
、 ロ、V、=−810V、 Vr=−70V。
Example 5 Selenium was deposited to a thickness of 1 on a 500 μm thick aluminum plate.
.. A charge generating layer was formed by vacuum deposition to a thickness of 5 μm, and then a solution prepared by dissolving 100 parts by weight of an ethylene compound represented by 2 in 7 μm of tetrahydrofuran (THF) and polymethyl methacrylate polymer (PMMA: Tokyo Kasei) 1
00 parts by weight dissolved in 700 parts by weight of toluene was applied using a wire bar to form a charge transport layer such that the film thickness after drying was 20 μm. This photoreceptor was corona charged at -6, OkV for 0.2 seconds, and the characteristics were determined according to Example 4. 1llll Constant L Tato:
, V, = -810V, Vr = -70V.

E 、、2 =3.9ルツクス・秒と良好な結果が得ら
れた。
A good result was obtained with E,,2=3.9 lux·sec.

実施例6 実施例1で処理された無金属フタロシアニン50重量部
、ポリエステル樹脂(商品名バイロン200:東洋紡製
)50重量部、PMMA50重量部とTHF溶剤ととも
に3時間混合機により混練して塗布液を調整し、アルミ
ニウム支持体上に約1μmになるように塗布し、電荷発
生層を形成した。次に、化合物Nα3で示されるエチレ
ン化合物100重量部、ポリカーボネート樹脂(パンラ
イトL −1250) 100重量部、シリコンオイル
0.1重量部をT HF700重量部とトルエン700
重量部で混合し、電荷発生層の上に約15μmとなるよ
うに塗布し、電荷輸送層を形成し感光体を作製した。
Example 6 50 parts by weight of the metal-free phthalocyanine treated in Example 1, 50 parts by weight of polyester resin (trade name Byron 200 manufactured by Toyobo), 50 parts by weight of PMMA and THF solvent were kneaded in a mixer for 3 hours to form a coating solution. The mixture was adjusted and coated on an aluminum support to a thickness of about 1 μm to form a charge generation layer. Next, 100 parts by weight of an ethylene compound represented by compound Nα3, 100 parts by weight of polycarbonate resin (Panlite L-1250), and 0.1 part by weight of silicone oil were mixed with 700 parts by weight of THF and 700 parts by weight of toluene.
The components were mixed in parts by weight and coated on the charge generation layer to a thickness of about 15 μm to form a charge transport layer to produce a photoreceptor.

このようにして得られた感光体に実施例5と同様にして
、−6,0kVのコロナ帯電を0.2秒間行い、特性を
測定したところ、V、 =−850V、 E l/2 
=4.1ルツクス・秒と良好な結果が得られた。
The thus obtained photoreceptor was corona charged at -6.0 kV for 0.2 seconds in the same manner as in Example 5, and its characteristics were measured. V, = -850 V, E l/2
= 4.1 lux·sec, a good result was obtained.

実施例7 化合物Nα4〜35それぞれについて実施例4と同様、
感光層を形成し感光体を作製しr S P−428Jを
用いて特性を測定した結果を第2表に示す。
Example 7 Same as Example 4 for each of compounds Nα4 to 35,
A photoreceptor was prepared by forming a photosensitive layer, and its characteristics were measured using rSP-428J. The results are shown in Table 2.

暗所で+6.0kVのコロナ放電を10秒間行い正帯電
せしめ、照度2ルツクスの白色光を照射した場合の半減
衰露光IE1/2(ルックス・秒)で示した。
A corona discharge of +6.0 kV was performed for 10 seconds in a dark place to positively charge the sample, and the half-attenuation exposure IE1/2 (lux seconds) was shown when white light with an illuminance of 2 lux was irradiated.

第2表に見られるように、化合物Nα4〜35を用いた
感光体にふいても良好な半減衰露光量が得られることが
判る。
As seen in Table 2, it can be seen that a good half-attenuation exposure amount can be obtained even when the photoreceptor using compounds Nα4-35 is wiped.

第 2 表(その1) 第 2 表(その2) 〔発明の効果〕 本発明によれば、導電性基体上に設ける感光層の電荷輸
送性物質として前記一般式(I)で示されるエチレン化
合物を用いる事としたため、正帯電および負帯電におい
ても高感度でしかも繰り返し特性の優れた感光体を得る
事ができる。また、電荷発生物質は露光光源の種類に対
応して好適な物質を選ぶことができ、−例をあげると7
タロンアニン化合物およびある種のビスアゾ化合物を用
いれば半導体レーザブリンク−に使用可能な感光体を得
ることができる。さらに、必要に応じて表面に被覆層を
設置して耐久性を向上することが可能である。
Table 2 (Part 1) Table 2 (Part 2) [Effects of the Invention] According to the present invention, the ethylene compound represented by the above general formula (I) is used as a charge transporting substance in the photosensitive layer provided on the conductive substrate. By using the photoreceptor, it is possible to obtain a photoreceptor with high sensitivity and excellent repeatability even in positive and negative charging. In addition, a suitable charge-generating substance can be selected depending on the type of exposure light source; for example, 7
By using talonanine compounds and certain bisazo compounds, it is possible to obtain photoreceptors that can be used for semiconductor laser blinking. Furthermore, if necessary, it is possible to provide a coating layer on the surface to improve durability.

【図面の簡単な説明】[Brief explanation of the drawing]

第1.2.3図は本発明の感光体のそれぞれ異なる実施
例を示す概念的断面図である。 ■ 導電性基体、3 電荷発生物質、・1 電荷発生層
、5 電荷輸送性物質、6 電荷輸送層、7 被覆層、
20.21.22  感光層。
1.2.3 are conceptual sectional views showing different embodiments of the photoreceptor of the present invention. ■ Conductive substrate, 3 charge-generating substance, 1 charge-generating layer, 5 charge-transporting substance, 6 charge-transporting layer, 7 coating layer,
20.21.22 Photosensitive layer.

Claims (1)

【特許請求の範囲】 1)下記一般式( I )で示されるエチレン化合物のう
ちの少なくとも一種類を含む感光層を有することを特徴
とする電子写真用感光体。 ▲数式、化学式、表等があります▼・・・( I ) (式( I )中、n、mはそれぞれ0〜5の整数、R_
1〜R_1_4はそれぞれ水素原子、ハロゲン原子、ヒ
ドロキシ基、アルキル基、アルコキシ基、アリル基、カ
ルボキシル基、エステル基、アリール基、シアノ基、ニ
トロ基、アミノ基、アルキルアミノ基、またはアリール
アミノ基を表す。R_1_5、R_1_6は水素原子、
低級アルキル基、またはアリール基を表す。)
[Scope of Claims] 1) An electrophotographic photoreceptor characterized by having a photosensitive layer containing at least one kind of ethylene compound represented by the following general formula (I). ▲There are mathematical formulas, chemical formulas, tables, etc.▼...(I) (In formula (I), n and m are each integers from 0 to 5, R_
1 to R_1_4 each represent a hydrogen atom, a halogen atom, a hydroxy group, an alkyl group, an alkoxy group, an allyl group, a carboxyl group, an ester group, an aryl group, a cyano group, a nitro group, an amino group, an alkylamino group, or an arylamino group. represent. R_1_5 and R_1_6 are hydrogen atoms,
Represents a lower alkyl group or an aryl group. )
JP30687886A 1986-12-23 1986-12-23 Electrophotographic sensitive body Pending JPS63158559A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP30687886A JPS63158559A (en) 1986-12-23 1986-12-23 Electrophotographic sensitive body

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP30687886A JPS63158559A (en) 1986-12-23 1986-12-23 Electrophotographic sensitive body

Publications (1)

Publication Number Publication Date
JPS63158559A true JPS63158559A (en) 1988-07-01

Family

ID=17962334

Family Applications (1)

Application Number Title Priority Date Filing Date
JP30687886A Pending JPS63158559A (en) 1986-12-23 1986-12-23 Electrophotographic sensitive body

Country Status (1)

Country Link
JP (1) JPS63158559A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0466094A2 (en) * 1990-07-10 1992-01-15 Canon Kabushiki Kaisha Electrophotographic photosensitive member

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0466094A2 (en) * 1990-07-10 1992-01-15 Canon Kabushiki Kaisha Electrophotographic photosensitive member
EP0757292A1 (en) * 1990-07-10 1997-02-05 Canon Kabushiki Kaisha Electrophotographic photosensitive member

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