JPH01107261A - Electrophotographic sensitive body - Google Patents

Electrophotographic sensitive body

Info

Publication number
JPH01107261A
JPH01107261A JP26511387A JP26511387A JPH01107261A JP H01107261 A JPH01107261 A JP H01107261A JP 26511387 A JP26511387 A JP 26511387A JP 26511387 A JP26511387 A JP 26511387A JP H01107261 A JPH01107261 A JP H01107261A
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
JP26511387A
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 JP26511387A priority Critical patent/JPH01107261A/en
Priority to US07/257,260 priority patent/US4957837A/en
Priority to DE3835108A priority patent/DE3835108C2/en
Publication of JPH01107261A publication Critical patent/JPH01107261A/en
Pending legal-status Critical Current

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, 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
    • G03G5/0664—Dyes
    • G03G5/0666—Dyes containing a methine or polymethine group
    • G03G5/0668—Dyes containing a methine or polymethine group containing only one methine or polymethine group
    • G03G5/067—Dyes containing a methine or polymethine group containing only one methine or polymethine group containing hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/28—Halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/42—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms with nitro or nitroso radicals directly attached to ring carbon atoms
    • C07D333/44—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms with nitro or nitroso radicals directly attached to ring carbon atoms attached in position 5
    • 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, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0622—Heterocyclic compounds
    • G03G5/0624—Heterocyclic compounds containing one hetero ring
    • G03G5/0627—Heterocyclic compounds containing one hetero ring being five-membered
    • G03G5/0629—Heterocyclic compounds containing one hetero ring being five-membered containing one hetero atom
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0622—Heterocyclic compounds
    • G03G5/0644—Heterocyclic compounds containing two or more hetero rings
    • G03G5/0661—Heterocyclic compounds containing two or more hetero rings in different ring systems, each system containing at least one hetero ring

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Photoreceptors In Electrophotography (AREA)

Abstract

PURPOSE:To improve the sensitivity and repeatability of an electrophotographic sensitive material by forming a photosensitive layer contg. at least one kind of specified hydrazone compd. on an electroconductive base body. CONSTITUTION:At least one kind of hydrazone compd. expressed by the formula I is incorporated in a photosensitive layer 20 formed on an electroconductive base body 1. In the formula I, R1 is a (substituted)aryl group; each R2-R7 is H, halogen, alkyl group, alkoxy group, phenoxy group, nitro group, hydroxy group, aryl group, or styryl group; in a zero or 1. By this constitution, an electrophotographic sensitive body having high sensitivity and high repeatability is obtd.

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、新規なヒドラゾン化合
物を含有すること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, it is characterized in that a novel hydrazone compound is contained in a photosensitive layer formed on a conductive substrate. The present invention relates to an electrophotographic photoreceptor.

〔従来の技術〕[Conventional technology]

従来より電子写真用感光体（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
Ｊ　　Ｎ−ビニルカルバゾールまたはポリビニルアント
ラセンなどの有機光導電性物質、フタワシアニン化合物
あるいはビスアゾ化合物などの有機光導電性物質、また
はこれら有機光導電性物質を樹脂結着剤中に分散させた
ものなどが利用されている。Conventionally, photosensitive materials for electrophotographic photoreceptors (hereinafter also referred to as photoreceptors) include 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
J Organic photoconductive substances such as N-vinylcarbazole or polyvinylanthracene, organic photoconductive substances such as futawashyanine compounds or bisazo compounds, or dispersions of these organic photoconductive substances in resin binders are used. has been done.

また感光体には暗所で表面電荷を保持する機能。The photoreceptor also has the ability to retain surface charge in the dark.

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
らの機能をあわせ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の保持と
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
体表面上への露光による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転写、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。It is necessary to have the function of receiving light and generating a charge, as well as the function of receiving light and transporting a charge. There is a so-called laminated photoreceptor in which functionally separated layers are laminated, including a layer that contributes to charge generation, a layer that contributes to surface charge retention in the dark, and a layer that contributes to charge transport during light reception. For example, the Carlson method is applied to image formation by electrophotography using these photoreceptors. Image formation in this method involves charging the photoconductor in a dark place by corona discharge, forming electrostatic latent images such as letters and pictures on the document by exposing the surface of the charged photoconductor, and This is done by developing a latent image with toner, transferring the developed toner image to a support such as paper, and fixing it. 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−ビニルカルバゾールと２．
４．７−ドリニトロフルオレンー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（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。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。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-vinylcarbazole and 2.
4,7-dolinitrofluoren-9-one (described in U.S. Pat. No. 3,484,237), a 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). 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]

上述のように、有機材料は無機材料にない多くの長所を
持つが、しかしながら、電子写真用感光体に要求される
すべての特性を充分満足するものが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。As mentioned above, organic materials have many advantages that inorganic materials do not have, but at present, no material has yet been obtained that fully satisfies all the characteristics required of electrophotographic photoreceptors. In particular, there were problems with photosensitivity and characteristics during repeated and continuous use.

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、本葵明によれば、下記一般
式（Ｉ）で示されるヒドラゾ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 Aoimei provides an electrophotographic photoreceptor having a photosensitive layer containing at least one type of hydrazone compound represented by the following general formula (I).

〔式（Ｉ）中、Ｒ３は置換基を有してもよいアリール基
を表し、Ｒ２，Ｒ３，Ｒ４，Ｒ５，Ｒ１およびＲ１はそ
れぞれ水素原子、ハロゲン原子、、アルキル基。[In formula (I), R3 represents an aryl group which may have a substituent, and R2, R3, R4, R5, R1 and R1 each represent a hydrogen atom, a halogen atom, or an alkyl group.

アルコキシ基、フェノキシ基、ニトロ基、ヒドロキシ基
、アリール基、スチリル基を表し、ｎは０または１を表
す。〕 〔作用〕 前記一般式（１）で示されるヒドラゾン化合物を感光層
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、これらヒドラゾ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、このような前記一般式（Ｉ）で示される特定
のヒドラゾン化合物を電荷輸送性物質として使用するこ
とが、電子写真特性の向上に極めてを効であることを見
出し、高感度で繰り返し特性の優れた感光体を得るに至
ったのである。It represents an alkoxy group, a phenoxy group, a nitro group, a hydroxy group, an aryl group, or a styryl group, and n represents 0 or 1. ] [Function] There is no known example in which a hydrazone compound represented by the above general formula (1) is used in a photosensitive layer. In order to achieve the above objective, the present inventors conducted a number of experiments on these hydrazone compounds while conducting intensive studies on various organic materials. We have discovered that the use of a specific hydrazone compound represented by the general formula (I) as a charge transporting substance is extremely effective in improving electrophotographic properties, and we have developed a photosensitive material with high sensitivity and excellent repeatability. He finally gained a body.

〔実施例〕〔Example〕

本発明に用いられる前記一般式（１）のヒドラゾン化合
物は、通常の方法により合成することができる。すなわ
ち、必要に応じて縮合剤として少量の酸を用い、アルコ
ールなどの適当な有機溶媒中でアルデヒド類またはカル
ボニル化合物とヒドラジン類を縮合させることにより得
られる。The hydrazone compound of the general formula (1) used in the present invention can be synthesized by a conventional method. That is, it can be obtained by condensing aldehydes or carbonyl compounds with hydrazines in a suitable organic solvent such as alcohol, using a small amount of acid as a condensing agent if necessary.

こうして得られる前記一般式（１）で表されるヒドラゾ
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 hydrazone compound represented by the general formula (1) thus obtained are as follows.

化合物ＮαＩ Ｎα２ 化合物Ｎα３ Ｎα４ Ｎｏ、　５ Ｎα６ Ｎα７ Ｎα８ Ｎα１Ｏ Ｎα１１ 化合物Ｎ（Ｌ　１５ Ｎα１６ Ｎα１７ Ｎα１８ ＩＬ　１９ Ｎα２０ 化合物Ｎα２１ Ｎα２４ Ｎα２６ Ｎ［Ｌ３２ Ｎｏ、　３６ Ｎα３７ 本発明の感光体は前述のようなヒドラゾン化合物を感光
層中に含有させたものであるが、これらヒドラゾン化合
物の応用の仕方によって、第１図。Compound NαI Nα2 Compound Nα3 Nα4 No, 5 Nα6 Nα7 Nα8 Nα1O Nα11 Compound N(L 15 Nα16 Nα17 Nα18 IL 19 Nα20 Compound Nα21 Nα24 Nα26 N[L32 No, 36 Nα37 Effects of the present invention The photobody is exposed to a hydrazone compound as mentioned above. However, depending on how these hydrazone compounds are applied, FIG.

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。It can be used as shown in FIG. 2 or 3.

第１図、第２図および第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で、１は導電性基体、２
０．２１．２２は感光層、３は電荷発生物質、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, 2, and 3 are conceptual cross-sectional views of different embodiments of the photoreceptor of the present invention, in which 1 is a conductive substrate, 2 is a conductive substrate, and 2 is a conductive substrate.
0.21.22 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であるヒドラゾン化合物を樹脂バインダー（結
着剤）中に分散した感光層２０（通常積層型感光体と称
せられる構成）が設けられた〕のである。FIG. 1 shows a photosensitive layer 20 (commonly called a laminated photoreceptor) in which a charge generating substance 3 and a hydrazone compound as a charge transporting substance 5 are dispersed in a resin binder on a conductive substrate l. ) was established].

第２図は、導電性基体ｌ上に電荷発生物質３を三体とす
る電荷発生層４と、電荷輸送性物質５でるるヒドラゾン
化合物を含有する電荷輸送層６と〕積層からなる感光層
２１（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。この構成の感光体は通常負帯電方式で用
いられる。FIG. 2 shows a photosensitive layer 21 consisting of a stack of a charge-generating layer 4 having three charge-generating substances 3 on a conductive substrate l, and a charge-transporting layer 6 containing a hydrazone compound containing a charge-transporting substance 5. (a configuration commonly referred to as a laminated photoreceptor). A photoreceptor having this configuration is normally used in a negative charging system.

第３図は、第２図の逆の層構成のものであり、通常正帯
電方式で用いられる。この場合には、電荷発生層４を保
護するためにさらに被覆層７を設けるのが一般的である
。FIG. 3 shows a layer structure opposite to that in FIG. 2, and is normally used in a positive charging system. In this case, it is common to further provide a coating layer 7 to protect the charge generation layer 4.

このように、積層型感光体として二種類の層構成をとる
理由としては、第２図の層構成の感光体を正帯電方式で
用いようとしても、これに適合する電荷輸送性物質は現
在まだ見つかっていないためである。現段階では、積層
型感光体で正帯電方式を適用する場合には、第３図に示
した層構成の感光体とすることが必要なのである。The reason why the laminated photoreceptor has two types of layer configurations is that even if a photoreceptor with the layer configuration shown in Figure 2 is used in a positive charging system, there is currently no charge transporting material that is compatible with this. This is because it has not been found. At present, when applying a positive charging method to a laminated type photoreceptor, it is necessary to use a photoreceptor having the layer structure shown in FIG.

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
、その上に電荷輸送性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 a 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−１乾燥し、さらに被覆層を形成するこ
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, and further forming a coating layer.

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、シアニン、スクアリリウム。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. Examples of the charge generating substance include phthalocyanine compounds such as metal-free phthalocyanine and titanyl phthalocyanine, various azo, quinone, and indigo pigments, or cyanine and squarylium.

アズレニウム、ピリリウム化合物などの染料や、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１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。Dyes such as azulenium and pyrylium compounds, selenium or selenium compounds, and the like are used, and a suitable substance can be selected depending on the light wave range of the exposure light source used for image formation. 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.

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て使用することが可能である。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−最大（Ｉ）で示されるヒドラゾン化合物を
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体などを用いることがで
きる。The charge transport layer 6 is a coating film in which a hydrazone compound represented by (I) above as an organic charge transport substance is dispersed in a resin binder, and serves as an insulating layer in a dark place to retain the charge of the photoreceptor. During light reception, it functions to transport charges injected from the charge generation layer. As a 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
消滅させ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、　Ｓ
ｉｎ□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
定されることはなく５ｉ０２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 to neutralize and eliminate the surface charges by injecting the generated charges. As the coating material, organic insulating film-forming materials such as polyester and polyamide can be used. In addition, these organic materials and glass resin, S
It is also possible to use a mixture of inorganic materials such as in□ and materials that reduce electrical resistance such as metals and metal oxides. The coating material is not limited to organic insulating film forming materials, but may also be formed using inorganic materials such as 5i02, metals, metal oxides, etc. by methods such as vapor deposition and sputtering. As mentioned above, it is desirable that the coating material be as transparent as possible in the wavelength region where the charge generating substance absorbs maximum light.

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Ｎα１で示され
るヒドラゾン化合物１００重量部をポリエステル樹脂（
商品名バイロン２００：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（Ａ　ｌ　−Ｐ　Ｅ　Ｔ　’
）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、第１図に示し
た構成の感光体を作製した。Example 1 A polyester resin (
A coating solution was prepared by kneading 100 parts by weight of Vylon 200 (trade name: manufactured by Toyobo) and a tetrahydrofuran (THF) solvent for 3 hours in a mixer, and then a coating solution was prepared using an aluminum vapor-deposited polyester film (A l -P ET ') as a conductive substrate.
), a photosensitive layer was formed by coating using a wire bar method so that the film thickness after drying would be 15 μm, thereby producing a photoreceptor having the structure shown in FIG. 1.

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、二つ
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
タロシアニンと作用小片としてテフロンピースを内蔵し
た非磁性罐体をおいて粉砕するＬ　Ｉ　ＭＭ　Ａ　Ｃ（
Ｌｉｎｅａｒ　Ｉｎｄｕｃｔｉｏｎ　Ｍｏｔｏｒ　Ｍｉ
ｘ−ｉｎｇ　ａｎｄ　Ｃｒａｓｈｉｎｇ　：富士電機部
）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ＤＭＦとを分離濾過し、乾燥して無金属フ
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 a non-magnetic case containing α-type metal-free phthalocyanine and a Teflon piece as a working piece is placed between two linear motors placed opposite each other to crush it. L I MM A C (
Linear Induction Motor Mi
X-ing and Crashing (Fuji Electric Department) treatment was performed 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 treated for metal-free phthalocyanine.

次に、前記化合物Ｎα２で示されるヒドラゾン化合物１
００重量部をテトラヒドロフラン（ＴＨＦ）７００重量
部に溶かした液とポリメタクリル酸メチルポリマー（Ｐ
ＭＭＡ　：東京化成製）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法にて塗
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）５
０重量部、ＰＭＭＡ５０重量部を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
ー法にて塗布し、乾燥後の膜厚が１μｍになるように電
荷発生層を形成し、第３図に示した構成に対応する感光
体を作製した。ただし、本発明に直接関与しない被覆層
は設けなかった。Next, a hydrazone compound 1 represented by the above compound Nα2
00 parts by weight dissolved in 700 parts by weight of tetrahydrofuran (THF) and polymethyl methacrylate polymer (P
MMA: manufactured by Tokyo Kasei Co., Ltd.) 100 parts by weight to 700 parts by weight of toluene
A coating solution prepared by mixing parts by weight of the solution was coated onto an aluminum-deposited polyester film substrate by a wire bar method to form a charge transport layer so that the film thickness after drying was 15 μm. 50 parts by weight of the above-treated metal-free phthalocyanine and a polyester resin (trade name: Vylon 200 manufactured by Toyobo Co., Ltd.) 5
0 parts by weight, 50 parts by weight of PMMA with THF solvent
A coating solution was prepared by kneading with a time mixer, and applied using a wire bar method to form a charge generation layer with a film thickness of 1 μm after drying. The body was created. However, a coating layer not directly related to the present invention was not provided.

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Ｎ１１３で示されるヒドラゾン化合物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、その他は実施例１と同様にして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, hydrazone compound 1 represented by compound N113
00 parts by weight, polyester resin (trade name Byron 200
A photosensitive layer was formed in the same manner as in Example 1 except that 50 parts by weight of PMMA and 50 parts by weight of PMMA were used to form a photosensitive layer 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プル−を用い、その他は実施例
１と同様にして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, except that a chlorodiapolymer, which is a bisazo pigment as disclosed in JP-A No. 47-37543, was used instead of the metal-free phthalocyanine. A photoreceptor was prepared.

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Ｖ、（ボルト）は暗所で＋６：　Ｏｋ
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
ｄ（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）を求め半減衰露光量ＥＩ７２（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Ｖｒ（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の単色光を用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（７８０ｎｍ）を照射して
半減衰露光量（μＪ／ｃａｔ）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 V (volts) of the photoreceptor is +6 in the dark: OK
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.
Measure d (volts), and then irradiate the surface of the photoreceptor with white light with an illuminance of 2 lux to find the time (seconds) it takes for V to be halved, and find the half-attenuation exposure amount EI72 (lux seconds). did. Further, the surface potential when white light with an illuminance of 2 lux was irradiated for 10 seconds was defined as the residual potential Vr (volt). In addition, when a phthalocyanine compound is used as a charge generating substance, high sensitivity with long wavelength light can be expected.
Electrophotographic properties using nm monochromatic light were also measured at the same time. That is, measurements are made in the same manner up to Vd, then 1 μW monochromatic light (780 nm) is irradiated instead of white light to determine the half-attenuation exposure amount (μJ/cat), 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の感光
体は半減衰露光量、残留電位ともに差異はなく、表面電
位でも良好な特性を示している。Table 1 As seen in Table 1, the photoreceptors of Examples 1, 2, and 3°4 had no difference in half-attenuation exposure or residual potential, and exhibited good characteristics in terms of surface potential.

また、７８０ｎｍの長波長光に対しても、フタロシアニ
ン化合物を電荷発生物質とした実施例１，２゜３の感光
体は優れた電子写真特性を示している。Further, even for long wavelength light of 780 nm, the photoreceptors of Examples 1, 2 and 3 in which a phthalocyanine compound was used as a charge generating substance exhibited excellent electrophotographic properties.

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Ｎα４で示されるヒドラゾン化合物１００重量部をテ
トラヒドロフラン（ＴＨＦ）７００重量部に溶かしだ液
とポリメタクリル酸メチルポリマー（ＰＭＭＡ　：東京
化成製）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ワイヤーバー法にて塗布
し、乾燥後の膜厚が２０μｍになるように電荷輸送層を
形成し、第２図に示した構成の感光体を作製した。この
感光体に−６，０ｋＶのコロナ帯電を０．２秒間行い電
子写真特性を測定したとコロ、　Ｖ、＝−６５０Ｖ、　
　Ｖ、＝−８０Ｖ、　　Ｅｌ／２＝４．８ルツクス・秒
と良好な結果が得られた。Example 5 Selenium was deposited to a thickness of 1 on a 500 μm thick aluminum plate.
．． A charge generation layer is formed by vacuum evaporation to a thickness of 5 μm, and then 100 parts by weight of a hydrazone compound represented by compound Nα4 is dissolved in 700 parts by weight of tetrahydrofuran (THF) and a polymethyl methacrylate polymer (PMMA: manufactured by Tokyo Kasei) is added. A coating solution prepared by mixing 100 parts by weight of toluene with 700 parts by weight of toluene was applied using a wire bar method to form a charge transport layer so that the film thickness after drying was 20 μm. A photoreceptor having the configuration shown in the figure was manufactured. This photoreceptor was corona charged at -6.0 kV for 0.2 seconds and its electrophotographic characteristics were measured. Coro, V, = -650 V.
Good results were obtained with V=-80V and El/2=4.8 lux·sec.

実施例６ 実施例１で処理さ、れた熱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重量部を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Ｎα５で示されるヒド
ラゾン化合物１００重蛍部、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ＴＨＦ７００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た。Example 6 50 parts by weight of the thermometallic phthalocyanine treated in Example 1, 50 parts by weight of polyester resin (trade name Byron 200 manufactured by Toyobo), and 50 parts by weight of PMMA were kneaded with a THF solvent in a mixer for 3 hours and applied. The solution was prepared 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 a hydrazone compound represented by compound Nα5, 100 parts by weight of polycarbonate resin (Panlite L-1250), and 0.1 parts by weight of silicone oil were mixed with 700 parts by weight of THF and 700 parts by weight of toluene to generate a charge. A charge transport layer was formed by coating the layer to a thickness of about 15 μm.

このようにして得られた感光体を実施例５と同様にして
、−６，０ｋＶのコロナ帯電を０．２秒間行い電子写真
特性を測定したとコロ、Ｖ　−＝−６８０Ｖ、　Ｅ　ｌ
／２＝５．９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 electrophotographic properties were measured.
/2=5.9 lux·sec, which was a good result.

実施例７ 化合物Ｎα６〜Ｎα４０それぞれについて実施例４と同
様にして感光層を形成して感光体とし、「５Ｐ−４２８
Ｊを用いて半減衰露光量を測定した結果を第２表に示す
。Example 7 A photoreceptor was formed by forming a photosensitive layer for each of the compounds Nα6 to Nα40 in the same manner as in Example 4.
Table 2 shows the results of measuring the half-attenuation exposure using J.

暗所で＋５．　ＱｋＶ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
減衰露光量Ｅ１／２（ルックス・秒）を示した。+5 in the dark. The half-attenuation exposure amount E1/2 (lux seconds) is shown when QkV corona discharge is performed for 10 seconds to positively charge the sample and white light with an illuminance of 2 lux is irradiated.

第　　２　　表　　（その１） 第　　２　　表　　（その２） 第　　２　　表　　（その３） 第２表に見られるように、前記ヒドラゾン化合物Ｎｏ、
　６〜Ｎα４０を用いた感光体についても、半減衰露光
量Ｅ　＋　／　２　＋すなわち感度は良好であった。Table 2 (Part 1) Table 2 (Part 2) Table 2 (Part 3) As seen in Table 2, the hydrazone compound No.
The half-attenuation exposure amount E + /2 +, that is, the sensitivity was also good for the photoreceptors using Nα6 to Nα40.

〔発明の効果〕〔Effect of the invention〕

本発明によれば、導電性基体上に電荷輸送性物質として
前記−最大（Ｉ）で示されるヒドラゾン化合物を用いる
こととしたため、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ことができ
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、−例をあげるとフタロシア
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
導体レーザプリンタ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。According to the present invention, since a hydrazone compound represented by -maximum (I) is used as a charge transporting substance on a conductive substrate, a photosensitive material with high sensitivity and excellent repeatability even in positive and negative charging can be obtained. You can get a body. In addition, a suitable charge-generating substance can be selected depending on the type of exposure light source; for example, by using phthalocyanine compounds and certain bisazo compounds, a photoreceptor that can be used in semiconductor laser printers can be obtained. be able to. 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】 第１図、第２図および第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。 １　導電性基体、３−　　電荷発生物質、４−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。 第　１　図 第　２　図 第３図BRIEF DESCRIPTION OF THE DRAWINGS FIGS. 1, 2, and 3 are conceptual sectional views showing different embodiments of the photoreceptor of the present invention. Reference Signs List 1 conductive substrate, 3- charge generating substance, 4- charge generating layer, 5 charge transporting substance, 6 charge transporting layer, 7 coating layer, 20.21.22 photosensitive layer. Figure 1 Figure 2 Figure 3

Claims (1)

【特許請求の範囲】 １）下記一般式（ I ）で示されるヒドラゾン化合物の
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、Ｒ＿１は置換基を有してもよいアリー
ル基を表し、Ｒ＿２、Ｒ＿３、Ｒ＿４、Ｒ＿５、Ｒ＿６
およびＲ＿７はそれぞれ水素原子、ハロゲン原子、アル
キル基、アルコキシ基、フェノキシ基、ニトロ基、ヒド
ロキシ基、アリール基、スチリル基を表し、ｎは０また
は１を表す。〕[Scope of Claims] 1) An electrophotographic photoreceptor comprising a photosensitive layer containing at least one hydrazone compound represented by the following general formula (I). ▲There are mathematical formulas, chemical formulas, tables, etc.▼...(I) [In formula (I), R_1 represents an aryl group that may have a substituent, R_2, R_3, R_4, R_5, R_6
and R_7 each represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a phenoxy group, a nitro group, a hydroxy group, an aryl group, or a styryl group, and n represents 0 or 1. ]
JP26511387A 1987-10-15 1987-10-20 Electrophotographic sensitive body Pending JPH01107261A (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
JP26511387A JPH01107261A (en) 1987-10-20 1987-10-20 Electrophotographic sensitive body
US07/257,260 US4957837A (en) 1987-10-15 1988-10-13 Photosensitive member for electrophotography containing hydrazone in charge transport layer
DE3835108A DE3835108C2 (en) 1987-10-15 1988-10-14 Electrophotographic recording material

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP26511387A JPH01107261A (en) 1987-10-20 1987-10-20 Electrophotographic sensitive body

Publications (1)

Publication Number Publication Date
JPH01107261A true JPH01107261A (en) 1989-04-25

Family

ID=17412792

Family Applications (1)

Application Number Title Priority Date Filing Date
JP26511387A Pending JPH01107261A (en) 1987-10-15 1987-10-20 Electrophotographic sensitive body

Country Status (1)

Country Link
JP (1) JPH01107261A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH03278061A (en) * 1990-03-08 1991-12-09 Fuji Electric Co Ltd Electrophotographic sensitive body

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH03278061A (en) * 1990-03-08 1991-12-09 Fuji Electric Co Ltd Electrophotographic sensitive body

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