JPH0545908A - Electrophotographic organic sensitive body - Google Patents

Electrophotographic organic sensitive body

Info

Publication number
JPH0545908A
JPH0545908A JP3207899A JP20789991A JPH0545908A JP H0545908 A JPH0545908 A JP H0545908A JP 3207899 A JP3207899 A JP 3207899A JP 20789991 A JP20789991 A JP 20789991A JP H0545908 A JPH0545908 A JP H0545908A
Authority
JP
Japan
Prior art keywords
charge generating
agent
potential
examples
organic
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
JP3207899A
Other languages
Japanese (ja)
Inventor
Hideo Nakamori
英雄 中森
Masafumi Tanaka
雅史 田中
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.)
Kyocera Mita Industrial Co Ltd
Original Assignee
Mita Industrial 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 Mita Industrial Co Ltd filed Critical Mita Industrial Co Ltd
Priority to JP3207899A priority Critical patent/JPH0545908A/en
Publication of JPH0545908A publication Critical patent/JPH0545908A/en
Pending legal-status Critical Current

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  • Photoreceptors In Electrophotography (AREA)

Abstract

PURPOSE:To provide the single layer dispersion type electrophotographic organic sensitive body restrained in residual potential to a low level and superior in sensitivity. CONSTITUTION:The electrophotographic organic sensitive body is provided on a conductive substrate 1 with an organic photosensitive layer 2 made of a composition comprising a charge generating material CG, a positive hole transfer material HT, and a benzoquinone derivative as an electron transfer material ET having a reduction potential of -0.8 to -1.3V, each dispersed into a resin medium.

Description

【発明の詳細な説明】Detailed Description of the Invention

【0001】[0001]

【産業上の利用分野】本発明は、複写機、レーザープリ
ンター等に有用な電子写真用有機感光体に関するもの
で、より詳細には感度や残留電位の改善された電子写真
用有機感光体に関する。
BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an electrophotographic organic photoreceptor useful for copying machines, laser printers and the like, and more particularly to an electrophotographic organic photoreceptor having improved sensitivity and residual potential.

【0002】[0002]

【従来の技術】デジタル光学系を用いた電子写真複写に
は、通常700nm以上の波長を有する光源が使用され
ている。この波長領域に感度を有する感光体として、有
機感光体(OPC)、アモルファスシリコン(α−S
i)、一部のセレン感光体等が知られているが、感度、
コスト等の総合的見地から、この分野ではOPCを使用
するケースが多い。
2. Description of the Related Art In electrophotographic copying using a digital optical system, a light source having a wavelength of 700 nm or more is usually used. Organic photoconductors (OPC), amorphous silicon (α-S) are used as photoconductors having sensitivity in this wavelength region.
i), some selenium photoreceptors are known, but the sensitivity,
From a comprehensive viewpoint of cost and the like, OPC is often used in this field.

【0003】有機感光体としては、電荷発生層(CG
L)と電荷輸送層(CTL)とを積層した所謂機能分離
型の有機感光体、即ち積層型の感光体が多いが、電荷輸
送物質の媒質中に電荷発生物質を分散させた単層分散型
の有機感光体も既に知られている。この種の感光体の電
荷輸送物質としては、キャリヤ移動度の高いものが要求
されているが、キャリヤ移動度の高い電荷輸送剤は殆ど
が正孔輸送性であるため、実用に供せられているものは
負帯電型の有機感光体に限られている。しかしながら、
負帯電型の有機感光体では、負極性コロナ放電を利用す
るためオゾンの発生量が多く、環境を汚染する、感光体
を劣化する等の問題があり、これを防止するため、オゾ
ンを発生させない格別の帯電システムや、生成オゾンを
分解するシステム、装置内のオゾンを排気するシステム
等、格別のシステムを必要とし、プロセスやシステムが
複雑化するという欠点がある。また、積層型感光体では
感光層の二度塗りが必要であったり、感光体層に電荷発
生層と電荷輸送層との界面が存在するため、干渉縞が発
生しやすいという光学上の問題がある。
As an organic photoreceptor, a charge generation layer (CG
L) and a charge transport layer (CTL) are stacked, so-called function-separated type organic photoconductors, that is, multi-layered photoconductors are often used, but a single layer dispersion type in which a charge generation substance is dispersed in a medium of a charge transport substance. The organic photoconductor of is also already known. As a charge transport material for this type of photoconductor, one having a high carrier mobility is required, but most of the charge transport agents having a high carrier mobility have a hole transporting property, so that they are practically used. What is present is limited to negatively charged organic photoconductors. However,
Negatively charged organic photoconductors use a negative corona discharge to generate a large amount of ozone, which causes problems such as environmental pollution and photodegradation. To prevent this, do not generate ozone. A special charging system, a system for decomposing generated ozone, a system for exhausting ozone in the apparatus, and the like are required, and there is a drawback that the process and the system are complicated. In addition, in the case of a laminated type photoreceptor, there is an optical problem that interference fringes are likely to occur because the photosensitive layer needs to be coated twice or the interface between the charge generation layer and the charge transport layer is present in the photoreceptor layer. is there.

【0004】単層分散型の有機感光体として特開昭59
−174849号公報には、ペリレン系顔料、PVK等
の光導電性ポリマー及び光導電性ポリマーに対して光学
増感作用を及ぼさない電子受容性物質の三成分を必須成
分として含む感光層を用いることが提案されている。ま
た、電子輸送能を有する電荷輸送物質の数少ない例とし
て、特開平1−206349号公報には、ジフェノキノ
ン構造を有する化合物が電子写真感光体用電荷輸送剤と
して提案されている。
As a single-layer dispersion type organic photoreceptor, JP-A-59 / 1984
JP-A-174849 discloses the use of a photosensitive layer containing, as essential components, three components of a perylene pigment, a photoconductive polymer such as PVK, and an electron-accepting substance that does not exert an optical sensitizing action on the photoconductive polymer. Is proposed. Further, as a few examples of charge transporting substances having electron transporting ability, JP-A-1-206349 proposes a compound having a diphenoquinone structure as a charge transporting agent for an electrophotographic photoreceptor.

【0005】[0005]

【発明が解決しようとする問題】前者の先行技術は、電
荷発生剤に対するアクセプターとして電子受容体を配合
するものであり、電子受容体の配合により確かに感度は
増大するが、この感光体では電子輸送が生じないため、
残留電位が未だ高いという問題がある。
In the former prior art, an electron acceptor is blended as an acceptor for a charge generating agent, and the sensitivity is certainly increased by blending the electron acceptor. Because no transportation occurs,
There is a problem that the residual potential is still high.

【0006】一方後者の先行技術で用いるジフェノキノ
ン誘導体は結着剤樹脂との相溶性も良く、良好な電子輸
送能を示すと言われているが、このジフェノキノン誘導
体を電荷輸送体として用いた積層感光体では、未だ残留
電位が高く、実用面での感度が十分でないという欠点が
ある。
On the other hand, the latter diphenoquinone derivative used in the prior art has a good compatibility with the binder resin and is said to exhibit a good electron transporting ability. The diphenoquinone derivative is used as a charge transporting layered photosensitive material. The body has a drawback that the residual potential is still high and the sensitivity in practical use is not sufficient.

【0007】一方、感光体の帯電極性について言えば、
正帯電或いは更に負帯電との両方に用いることができれ
ば、感光体の応用範囲を更に広げることができ、前述し
た種々の欠点を解消し得る点で著しく有利である。ま
た、有機感光体を単層の分散型で使用できれば感光体の
製造を容易にし、被膜欠陥の発生を防止し、光学的特性
を向上させる上でも、多くの利点が達成される。
On the other hand, regarding the charging polarity of the photoconductor,
If it can be used for both positive charging and negative charging, the range of application of the photoconductor can be further widened, and it is extremely advantageous in that various drawbacks described above can be eliminated. Further, if the organic photoreceptor can be used in a single layer dispersion type, many advantages are achieved in terms of facilitating the production of the photoreceptor, preventing the occurrence of coating defects, and improving the optical characteristics.

【0008】本発明者等は、電子輸送剤として、還元電
位が−0.8V〜−1.3Vのベンゾキノン誘導体を選
択し、これを正孔輸送剤と組合せ、電荷発生剤と共に樹
脂媒質中に分散させて、単層分散型有機感光体とする
と、感光体の残留電位を低下させ、感度を向上させ得る
ことを見出した。
The inventors of the present invention selected a benzoquinone derivative having a reduction potential of -0.8 V to -1.3 V as an electron transfer agent, combined it with a hole transfer agent, and put it in a resin medium together with a charge generating agent. It has been found that, when dispersed into a single-layer dispersion type organic photoconductor, the residual potential of the photoconductor can be lowered and the sensitivity can be improved.

【0009】本発明の目的は、単層分散型で、残留電位
が低いレベルに抑制され、しかも優れた感度を示す電子
写真用有機感光体を提供するにある。本発明の他の目的
は、正帯電或いは両帯電が可能で、特にデジタル電子写
真の用途に有用な有機感光体を提供するにある。
An object of the present invention is to provide an organic photoconductor for electrophotography, which is of a single-layer dispersion type and has a residual potential suppressed to a low level and excellent sensitivity. Another object of the present invention is to provide an organic photoreceptor which can be positively charged or both charged and which is particularly useful for digital electrophotography.

【0010】[0010]

【問題点を解決するための手段】本発明によれば、導電
性基体上に有機感光層を設けた電子写真用有機感光体に
おいて、有機感光層が樹脂媒質中に分散された電荷発生
剤、正孔輸送剤および電子輸送剤としての還元電位が−
0.8V〜−1.3Vのベンゾキノン誘導体から成る組
成物である有機感光体が提供される。本発明に用いる有
機感光体は、前記「化1」で表わされるものが好まし
い。また、本発明に用いる電荷発生剤は、5.3乃至
5.6eVのイオン化ポテンシャルを有するもの、特に
X型無金属フタロシアニンであることが好ましく、更に
正孔輸送剤はこれとマッチしたもの、即ち5.3乃至
5.6eVのイオン化ポテンシャルを有するもの、特に
アルキル置換トリフェニルジアミン誘導体であることが
好ましい。
According to the present invention, in an electrophotographic organic photoreceptor having an organic photosensitive layer on a conductive substrate, a charge generating agent in which the organic photosensitive layer is dispersed in a resin medium, The reduction potential as a hole transfer material and an electron transfer material is −
Provided is an organophotoreceptor, which is a composition comprising a 0.8V to -1.3V benzoquinone derivative. The organic photoconductor used in the present invention is preferably the one represented by the above-mentioned "Chemical formula 1". Further, the charge generating agent used in the present invention is preferably one having an ionization potential of 5.3 to 5.6 eV, particularly X-type metal-free phthalocyanine, and the hole transporting agent which matches this, A compound having an ionization potential of 5.3 to 5.6 eV, particularly an alkyl-substituted triphenyldiamine derivative is preferable.

【0011】[0011]

【作用】本発明によれば、電子輸送剤として還元電位
(その測定は後述する実施例記載の方法による)が−
0.8V〜−1.3Vのベンゾキノン誘導体を選択し、
これを正孔輸送剤と組合せ、電荷発生剤と共に樹脂煤質
中に分散させて、単層分散型有機感光体とすると、感光
体の残留電位を低下させ、感度を向上させることができ
る。
According to the present invention, the electron transfer agent has a reduction potential (measurement is carried out by the method described in Examples below).
Select a benzoquinone derivative of 0.8V to -1.3V,
When this is combined with a hole transport material and dispersed in a resin soot together with a charge generating agent to form a single-layer dispersion type organic photoreceptor, the residual potential of the photoreceptor can be lowered and the sensitivity can be improved.

【0012】本発明者等の研究によると、ベンゾキノン
誘導体の還元電位と感光体の電位コントラスト(未露光
部の電位と露光部の残留電位との差で、感度と残留電位
との両方が影響する)との間には一定の関係があり、還
元電位が一定の範囲のベンゾキノン誘導体は、上記各成
分との組合せで感光体の電位コントラストを顕著に向上
せしめることが判明した。
According to the research conducted by the present inventors, both the reduction potential of the benzoquinone derivative and the potential contrast of the photoconductor (the difference between the potential of the unexposed portion and the residual potential of the exposed portion affect both the sensitivity and the residual potential). It has been found that a benzoquinone derivative having a constant reduction potential in a certain range can remarkably improve the potential contrast of the photoconductor in combination with each of the above components.

【0013】図1は、電荷発生剤、正孔輸送剤及び種々
のベンゾキノン誘導体を一定の量比で樹脂中に含む単層
分散型有機感光体(詳細は後述する実施例参照)につい
て、ベンゾキノン誘導体の還元電位と感光体の電位コン
トラストとの関係をプロットしたものであり、還元電位
が本発明の範囲にあるベンゾキノン誘導体を選択するこ
とにより、電位コントラストの顕著な向上、即ち感度の
増大と残留電位の低減とが可能となることが了解され
る。
FIG. 1 shows a benzoquinone derivative of a single-layer dispersion type organic photoconductor containing a charge generating agent, a hole transporting agent, and various benzoquinone derivatives in a resin in a fixed amount ratio (for details, refer to Examples described later). Is a plot of the relationship between the reduction potential and the potential contrast of the photoconductor. By selecting a benzoquinone derivative having a reduction potential within the range of the present invention, the potential contrast is remarkably improved, that is, the sensitivity and the residual potential are increased. It is understood that the reduction of

【0014】本発明に用いるベンゾキノン誘導体は電子
受容性物質として公知のものであるが、前記範囲の還元
電位を有するベンゾキノン誘導体が電子輸送を行うとい
う事実は本発明によって始めて見出されたものである。
The benzoquinone derivative used in the present invention is known as an electron-accepting substance, but the fact that a benzoquinone derivative having a reduction potential in the above range carries out electron transport was first discovered by the present invention. ..

【0015】本発明の電子写真用有機感光体における電
荷像生成原理を説明する図2において、導電性基体1上
には、単層分散型の有機感光体層2が設けられており、
この有機感光体層2には電荷発生剤CG、ベンゾキノン
誘導体から成る電子輸送剤ET及び正孔輸送剤HTが分
散している。露光に先立った帯電工程により、有機感光
体層2の表面には正(+)に帯電されており、導電性基
体表面には負電荷(−)が誘導されている。この状態で
光線(hν)を照射すると、電荷発生剤CGには電荷が
発生し、電子は電子輸送剤ETに注入され、有機感光体
層2の表面に移動して、正電荷(+)を打ち消す。一
方、正孔(+)は正孔輸送剤HTに注入されて、途中で
トラップされることなく、導電性基体1の表面に移動し
て負電荷(−)により打ち消される。以上により、電荷
像が生成する。
Referring to FIG. 2 for explaining the principle of charge image generation in the electrophotographic organic photoreceptor of the present invention, a monolayer-dispersed organic photoreceptor layer 2 is provided on a conductive substrate 1.
In this organic photoreceptor layer 2, a charge generating agent CG, an electron transfer agent ET composed of a benzoquinone derivative and a hole transfer agent HT are dispersed. By the charging process prior to the exposure, the surface of the organic photoconductor layer 2 is positively (+) charged and the surface of the conductive substrate is negatively charged (-). When a light ray (hν) is irradiated in this state, an electric charge is generated in the charge generation agent CG, electrons are injected into the electron transfer agent ET, move to the surface of the organic photoconductor layer 2, and a positive charge (+) is generated. Cancel. On the other hand, the holes (+) are injected into the hole transport material HT, move to the surface of the conductive substrate 1 without being trapped in the middle, and are canceled by the negative charge (−). As described above, the charge image is generated.

【0016】本発明で電子輸送剤ETとして還元電位が
−0.8V〜−1.3Vのベンゾキノン誘導体を使用す
るのは、このものが電子輸送性に優れていることに基づ
くものであり、これは分子骨格の両端末に電子受容性に
優れたキノン系酸素原子が結合しており、また分子鎖全
体にわたって共役二重結合があって、構造内の電子の移
動が容易で、しかも電子の授受が容易に行われることに
関係しているものと思われる。更に、還元電位が−0.
8V〜−1.3Vの範囲を外れると電荷発生剤で発生し
た電子(キャリヤ)の注入が困難であるのに対して、還
元電位が−0.8V〜−1.3Vの誘導体では電子の注
入が容易に行われるものと認められる。
The reason why the benzoquinone derivative having a reduction potential of -0.8 V to -1.3 V is used as the electron transporting agent ET in the present invention is that this is excellent in electron transporting property. Is a quinone-based oxygen atom with excellent electron-accepting properties bound to both terminals of the molecular skeleton, and also has a conjugated double bond throughout the molecular chain, which facilitates the transfer of electrons within the structure and the transfer of electrons. Seems to be related to being done easily. Furthermore, the reduction potential is −0.
If it is out of the range of 8V to -1.3V, it is difficult to inject the electrons (carriers) generated by the charge generating agent, whereas in the derivative having the reduction potential of -0.8V to -1.3V, the injection of electrons is difficult. It is recognized that

【0017】一方、電荷輸送剤として、正孔輸送剤HT
と電子輸送剤ETとが共存する系では、両者の間の相互
作用、一層具体的には電荷移動錯体の形成に注意する必
要がある。両者の間にこのような錯体が形成されると、
正孔と電子との間に再結合が生じ、全体として電荷の移
動度が低下する。正孔輸送剤HTのイオン化ポテンシャ
ルが本発明の範囲よりも小さい場合には、電子輸送剤E
Tとの間に錯体を形成する傾向が大きくなり、電子−正
孔の再結合が生じるために、見掛の量子収率が低下し、
感度の低下に結びつくものと思われる。
On the other hand, as a charge transport material, a hole transport material HT
In a system in which the and the electron transfer agent ET coexist, it is necessary to pay attention to the interaction between the two and more specifically to the formation of the charge transfer complex. When such a complex is formed between the two,
Recombination occurs between holes and electrons, and the charge mobility as a whole decreases. When the ionization potential of the hole transfer material HT is smaller than the range of the present invention, the electron transfer material E
Since the tendency to form a complex with T increases and electron-hole recombination occurs, the apparent quantum yield decreases,
It is thought to lead to a decrease in sensitivity.

【0018】本発明では、電子輸送剤として「化1」の
ベンゾキノン誘導体を用いることが特に望ましい。第一
に、電子供与性置換基の導入はこの誘導体の電子親和力
を本発明の範囲内とする作用をもたらす。因みに電子吸
引性基を導入したハロゲン置換ベンゾキノン誘導体の還
元電位は−0.6乃至−0.2Vのオーダーである。第
二に、ベンゾキノンは、感光層形成に用いる溶媒に対す
る溶解性が低く、感光層媒質となる樹脂に対しても相溶
性が低いという問題があるが、このベンゾキノン類に対
してアルキル基電子供与性置換基を導入し、好適にはこ
の導入の仕方を非対称のものとすることにより、溶媒に
対する溶解性や、樹脂媒質に対する相溶性を向上させ
て、高濃度の電子輸送剤を分散させることにより、電子
輸送性を向上させることができる。第三にベンゾキノン
類に置換基、特に崇高な置換基を導入することにより、
この誘導体に立体障害性が付与され、正孔輸送剤HTと
の間の錯体形成傾向が抑制され、感度を向上させること
ができる。
In the present invention, it is particularly desirable to use the benzoquinone derivative of "Chemical Formula 1" as the electron transfer agent. First, the introduction of an electron-donating substituent brings about the effect of keeping the electron affinity of this derivative within the scope of the present invention. Incidentally, the reduction potential of the halogen-substituted benzoquinone derivative having an electron-withdrawing group introduced is on the order of -0.6 to -0.2V. Secondly, benzoquinone has a problem that it has a low solubility in a solvent used for forming a photosensitive layer and a low compatibility with a resin as a photosensitive layer medium. By introducing a substituent, preferably by making the method of introduction asymmetric, by improving the solubility in a solvent and the compatibility with a resin medium, by dispersing a high concentration of the electron transfer agent, The electron transport property can be improved. Thirdly, by introducing a substituent, especially a sublime substituent, into benzoquinones,
Steric hindrance is imparted to this derivative, the tendency of complex formation with the hole transport material HT is suppressed, and sensitivity can be improved.

【0019】本発明において、電荷発生剤として、イオ
ン化ポテンシャルが5.3乃至5.6eV、特に、5.
32乃至5.38eVのものを用いるが、残留電位の抑
制、感度の向上の点で望ましく、また正孔輸送剤として
も上記電荷発生剤とバランスしたイオン化ポテンシャル
を有するものが好ましい。即ち、電荷発生剤CGから正
孔輸送剤HTへの電荷の注入のし易さは、電荷発生剤C
G、正孔輸送剤HTのイオン化ポテンシャルと密接に関
連しており、CGやHTのイオン化ポテンシャルが本発
明範囲よりも大きい場合には、電荷発生剤CGから正孔
輸送剤HTへの電荷の注入の程度が低くなるか、或いは
正孔輸送剤HT間での正孔の授受の程度が低くなるため
感度の低下が生じるものと認められる。
In the present invention, the charge generating agent has an ionization potential of 5.3 to 5.6 eV, particularly 5.
A compound having a dose of 32 to 5.38 eV is used, but it is preferable in terms of suppressing the residual potential and improving the sensitivity, and as the hole transferring material, a material having an ionization potential balanced with the charge generating agent is preferable. That is, the ease with which the charge is injected from the charge generating agent CG to the hole transporting agent HT depends on the charge generating agent C.
G, which is closely related to the ionization potential of the hole transfer material HT, and when the ionization potential of CG or HT is larger than the range of the present invention, injection of charges from the charge generation material CG to the hole transfer material HT. It is recognized that the sensitivity is lowered due to the decrease in the number of holes or the degree of transfer of holes between the hole transport materials HT.

【0020】[0020]

【発明の好適態様】本発明に用いる電子輸送物質は、還
元電位が−0.8V〜−1.3Vの範囲にあるベンゾキ
ノン誘導体で、特に前記「化1」で表わされるものであ
る。「化1」において、電子供与性基としてはメチル
基、エチル基、プロピル基、ブチル基等のアルキル基;
フェニル基、トリル基、クミル基等のアリール基;メト
キシ基、エトキシ基、プロポキシ基等のアルコキシ基;
ジメチルアミノ基、ジエチルアミノ基等のアミノ基;等
を挙げることができるが、例示したものに限定されな
い。
BEST MODE FOR CARRYING OUT THE INVENTION The electron transporting material used in the present invention is a benzoquinone derivative having a reduction potential in the range of -0.8 V to -1.3 V, and is particularly one represented by the above "Chemical formula 1". In "Chemical formula 1," the electron-donating group is an alkyl group such as a methyl group, an ethyl group, a propyl group, and a butyl group;
Aryl groups such as phenyl group, tolyl group, cumyl group; alkoxy groups such as methoxy group, ethoxy group, propoxy group;
Examples thereof include amino groups such as dimethylamino group and diethylamino group; however, the present invention is not limited thereto.

【0021】置換基の数は1個以上、好ましくは2乃至
4個であり、R1 及びR2 の2個が置換基であるもの、
R1 及びR3 の2個が置換基であるもの、R1 及びR4
の2個が置換基であるもの、R1 ,R2 及びR3 の3個
が置換基であるもの、R1 ,R2 ,R3 及びR4 の全て
が置換基であるものが挙げられる。
The number of substituents is 1 or more, preferably 2 to 4, and two of R1 and R2 are substituents,
Two of R1 and R3 being substituents, R1 and R4
2 are the substituents, three of R1, R2 and R3 are the substituents, and all of R1, R2, R3 and R4 are the substituents.

【0022】好適な誘導体の例は次の通りである。 2,6−ジメチル−p−ベンゾキノン 2,6−ジtert−ブチル−p−ベンゾキノン 1−メチル−p−ベンゾキノン 1−メトキシ−p−ベンゾキノン p−ベンゾキノン テトラメチル−p−ベンゾキノンExamples of suitable derivatives are: 2,6-Dimethyl-p-benzoquinone 2,6-ditert-butyl-p-benzoquinone 1-methyl-p-benzoquinone 1-methoxy-p-benzoquinone p-benzoquinone tetramethyl-p-benzoquinone

【0023】正孔輸送剤としては、前述した条件を満足
する限り、任意の正孔輸送物質が使用され、例えばオキ
サジアゾール系化合物、スチリル化合物、カルバゾール
系化合物、有機ポリシラン化合物、ピラゾリン化合物、
ヒドラゾン化合物、トリフェニルアミン系化合物、イン
ドール系化合物、オキサゾール系化合物、イソオキサゾ
ール系化合物、チアゾール系化合物、チアジアゾール系
化合物、イミダゾール系化合物、ピラゾール系化合物、
トリアゾール系化合物等の含窒素還式化合物、縮合多還
式化合物の内、イオン化ポテンシャルが5.3乃至5.
6eVのものが使用される。また、電界強度3×10
- 5 V/cmで10- 6 Vcm以上の移動度を有するも
のが特によい。
As the hole-transporting agent, any hole-transporting substance can be used as long as the above-mentioned conditions are satisfied. Examples thereof include oxadiazole compounds, styryl compounds, carbazole compounds, organic polysilane compounds, pyrazoline compounds,
Hydrazone compounds, triphenylamine compounds, indole compounds, oxazole compounds, isoxazole compounds, thiazole compounds, thiadiazole compounds, imidazole compounds, pyrazole compounds,
Of the nitrogen-containing reduction-type compounds such as triazole-based compounds and the condensed poly-reduction-type compounds, the ionization potential is 5.3 to 5.
A 6 eV one is used. In addition, the electric field strength 3 × 10
- at 5 V / cm 10 - particularly good those having 6 Vcm or more mobility.

【0024】好適な正孔輸送剤は、これに限定されない
が、1,1−ビス(p−ジエチルアミノフェニル)−
4,4ジフェニル−1,3−ブタジエン、N,N′−ビ
ス(o,p−ジメチルフェニル)−N,N′−ジフェニ
ルベンジジン、3,3′−ジメチル−N,N,N′,
N′−テトラキス−4−メチルフェニル(1,1′−ビ
フェニル)−4,4′−ジアミン、N−エチル−3−カ
ルバゾリルアルデヒド−N,N′−ジフェニルヒドラゾ
ン、4−[N,N−ビス(p−トルイル)アミノ]−β
−フェニルスチルベン等である。
Suitable hole transport agents include, but are not limited to, 1,1-bis (p-diethylaminophenyl)-
4,4 diphenyl-1,3-butadiene, N, N'-bis (o, p-dimethylphenyl) -N, N'-diphenylbenzidine, 3,3'-dimethyl-N, N, N ',
N'-tetrakis-4-methylphenyl (1,1'-biphenyl) -4,4'-diamine, N-ethyl-3-carbazolylaldehyde-N, N'-diphenylhydrazone, 4- [N, N -Bis (p-toluyl) amino] -β
-Phenylstilbene and the like.

【0025】電荷発生剤としては、例えば、セレン、セ
レン−テルル、アモルファスシリコン、ピリリウム塩、
アゾ系顔料、ジスアゾ系顔料、アンサンスロン系顔料、
フタロシアニン系顔料、インジコ系顔料、スレン系顔
料、トルイジン系顔料、ピラゾリン系顔料、ペリレン系
顔料、キナクリドン系顔料等が例示され、所望の領域に
吸収波長域を有するよう、一種または二種以上混合して
用いられる。イオン化ポテンシャルが5.3乃至5.6
の範囲にあるものが好適であり、特に好適なものとし
て、次のものが例示される。X型メタルフリーフタロシ
アニン、オキソチタニルフタロシアニン。
Examples of the charge generating agent include selenium, selenium-tellurium, amorphous silicon, pyrylium salt,
Azo pigments, disazo pigments, ansanthuron pigments,
Examples include phthalocyanine pigments, indico pigments, slene pigments, toluidine pigments, pyrazoline pigments, perylene pigments, quinacridone pigments, etc. Used. Ionization potential is 5.3 to 5.6
The following are exemplified as particularly preferable ones. X-type metal-free phthalocyanine, oxotitanyl phthalocyanine.

【0026】また、上記の各剤を分散させる樹脂媒質と
しては、種々の樹脂が使用でき、例えば、スチレン系重
合体、アクリル系重合体、スチレン−アクリル系重合
体、エチレン−酢酸ビニル共重合体、ポリプロピレン、
アイオノマー等のオレフィン系重合体、ポリ塩化ビニ
ル、塩化ビニル−酢酸ビニル共重合体、ポリエステル、
アルキッド樹脂、ポリアミド、ポリウレタン、エポキシ
樹脂、ポリカーボネート、ポリアリレート、ポリスルホ
ン、ジアリルフタレート樹脂、シリコーン樹脂、ケトン
樹脂、ポリビニルブチラール樹脂、ポリエーテル樹脂、
フェノール樹脂や、エポキシアクリレート等の光硬化型
樹脂等、各種の重合体が例示できる。これらの結着樹脂
は、一種または二種以上混合して用いることもできる。
好適な樹脂は、スチレン系重合体、アクリル系重合体、
スチレン−アクリル系重合体、ポリエステル、アルキッ
ド樹脂、ポリカーボネート、ポリアリレート等である。
Various resins can be used as the resin medium in which the above-mentioned respective agents are dispersed. For example, a styrene-based polymer, an acrylic-based polymer, a styrene-acrylic-based polymer, an ethylene-vinyl acetate copolymer. ,polypropylene,
Olefin-based polymers such as ionomers, polyvinyl chloride, vinyl chloride-vinyl acetate copolymers, polyesters,
Alkyd resin, polyamide, polyurethane, epoxy resin, polycarbonate, polyarylate, polysulfone, diallyl phthalate resin, silicone resin, ketone resin, polyvinyl butyral resin, polyether resin,
Examples include various polymers such as a phenol resin and a photocurable resin such as epoxy acrylate. These binder resins may be used alone or in combination of two or more.
Suitable resins include styrene polymers, acrylic polymers,
Examples thereof include styrene-acrylic polymer, polyester, alkyd resin, polycarbonate, polyarylate and the like.

【0027】本発明の感光体において、電荷発生剤は固
形分当たり0.1乃至5重量%、特に0.25乃至2.
5重量%の量で感光層中に含有されるのがよく、またベ
ンゾキノン誘導体(ET)は、固形分当たり5乃至50
重量%、特に10乃至40重量%、一方正孔輸送剤(H
T)は、固形分当たり5乃至50重量%、特に10乃至
40重量%で夫々感光層中に含有されるのがよい。更に
ET:HTの重量比は1:9乃至9:1、特に2:8乃
至8:2の範囲にあるのが最もよい。
In the photoreceptor of the present invention, the charge generating agent is 0.1 to 5% by weight, preferably 0.25 to 2.
The benzoquinone derivative (ET) may be contained in the photosensitive layer in an amount of 5% by weight, and the benzoquinone derivative (ET) may be contained in an amount of 5 to 50% by solid content.
% By weight, especially 10 to 40% by weight, while the hole transporting agent (H
T) is preferably contained in the photosensitive layer in an amount of 5 to 50% by weight, particularly 10 to 40% by weight, based on the solid content. Further, the ET: HT weight ratio is best in the range of 1: 9 to 9: 1, especially 2: 8 to 8: 2.

【0028】本発明の感光体形成用組成物には、電子写
真学的特性に悪影響を及ぼさない範囲で、それ自体公知
の種々の配合剤、例えば酸化防止剤、ラジカル補捉剤、
一重項クエンチャー、UV吸収剤、軟化剤、表面改質
剤、消泡剤、増量剤、増粘剤、分散安定剤、ワックス、
アクセプター、ドナー等を配合させることができる。
The composition for forming a photoreceptor of the present invention contains various compounding agents known per se, such as an antioxidant and a radical scavenger, as long as the electrophotographic properties are not adversely affected.
Singlet quencher, UV absorber, softener, surface modifier, defoamer, extender, thickener, dispersion stabilizer, wax,
An acceptor, a donor, etc. can be blended.

【0029】本発明によれば、全固形分当たり0.1乃
至50重量%の立体障害性フェノール系酸化防止剤を配
合すると、電子写真学的特性に悪影響を与えることな
く、感光層の耐久性を顕著に向上させ得ることがわかっ
た。適当な酸化防止剤は次の通りである。2,6−ジt
−ブチル−p−クレゾール;
According to the present invention, when the sterically hindered phenolic antioxidant is added in an amount of 0.1 to 50% by weight based on the total solid content, the durability of the photosensitive layer is not adversely affected without adversely affecting the electrophotographic characteristics. It has been found that can be significantly improved. Suitable antioxidants are as follows: 2,6-di t
-Butyl-p-cresol;

【0030】[0030]

【化2】 [Chemical 2]

【0031】[0031]

【化3】 [Chemical 3]

【0032】[0032]

【化4】 [Chemical 4]

【0033】[0033]

【化5】 [Chemical 5]

【0034】[0034]

【化6】 [Chemical 6]

【0035】[0035]

【化7】 [Chemical 7]

【0036】[0036]

【化8】 [Chemical 8]

【0037】塗布液を形成するのに使用する溶剤として
は、種々の有機溶剤が使用でき、メタノール、エタノー
ル、イソプロパノール、ブタノール等のアルコール類、
n−ヘキサン、オクタン、シクロヘキサン等の脂肪族系
炭化水素、ベンゼン、トルエン、キシレン等の芳香族炭
化水素、ジクロロメタン、ジクロロエタン、四塩化炭
素、クロロベンゼン等のハロゲン化炭化水素、ジメチル
エーテル、ジエチルエーテル、テトラヒドロフラン、エ
チレングリコールジメチルエーテル、ジエチレングリコ
ールジメチルエーテル等のエーテル類、アセトン、メチ
ルエチルケトン、シクロヘキサノン等のケトン類、酢酸
エチル、酢酸メチル等のエステル類、ジメチルホルムア
ミド、ジメチルスルホキシド等、種々の溶剤が例示さ
れ、一種または二種以上混合して用いられる。塗布液の
固形分濃度は一般に5乃至50%とするのがよい。
As the solvent used for forming the coating liquid, various organic solvents can be used, and alcohols such as methanol, ethanol, isopropanol and butanol,
Aliphatic hydrocarbons such as n-hexane, octane and cyclohexane, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as dichloromethane, dichloroethane, carbon tetrachloride and chlorobenzene, dimethyl ether, diethyl ether, tetrahydrofuran, Ethylene glycol dimethyl ether, ethers such as diethylene glycol dimethyl ether, acetone, methyl ethyl ketone, ketones such as cyclohexanone, ethyl acetate, esters such as methyl acetate, dimethylformamide, dimethylsulfoxide, etc., various solvents are exemplified, and one or more kinds Used as a mixture. Generally, the solid content concentration of the coating liquid is preferably 5 to 50%.

【0038】導電性基板としては、導電性を有する種々
の材料が使用でき、例えば、アルミニウム、銅、錫、白
金、金、銀、バナジウム、モリブデン、クロム、カドミ
ウム、チタン、ニッケル、インジウム、ステンレス綱、
真鍮等の金属単体や、上記金属が蒸着またはラミネート
されたプラスチック材料、ヨウ化アルミニウム、酸化
錫、酸化インジウム等で被覆されたガラス等が例示され
る。
As the conductive substrate, various conductive materials can be used. For example, aluminum, copper, tin, platinum, gold, silver, vanadium, molybdenum, chromium, cadmium, titanium, nickel, indium, stainless steel. ,
Examples include simple metals such as brass, plastic materials in which the above metals are vapor-deposited or laminated, and glass covered with aluminum iodide, tin oxide, indium oxide, or the like.

【0039】本発明の感光体では、単層分散型の感光体
であり、干渉縞等の発生がないことから、通常のアルミ
ニウム素管、特に膜厚が1乃至50μmとなるようにア
ルマイト処理を施した素管を用い得ることも利点の一つ
である。尚、塗布液を形成するには、電荷発生材料等と
結着樹脂等を、従来公知の方法、例えば、ロールミル、
ボールミル、アトライタ、ペイントシェイカーあるいは
超音波分散器等を用いて調製し、従来公知の塗布手段に
より塗布、乾燥すればよい。感光層の厚みは、特に制限
されないが、一般に5乃至100μm、特に10乃至5
0μmの範囲になることが望ましい。
The photoconductor of the present invention is a monolayer dispersion type photoconductor, and since it does not generate interference fringes or the like, it is alumite-treated so that the thickness of the ordinary aluminum tube is 1 to 50 μm. One of the advantages is that the applied blank tube can be used. Incidentally, in order to form the coating liquid, a charge generating material and the like and a binder resin and the like are prepared by a conventionally known method such as a roll mill,
It may be prepared by using a ball mill, an attritor, a paint shaker, an ultrasonic disperser, or the like, coated by a conventionally known coating means, and dried. The thickness of the photosensitive layer is not particularly limited, but is generally 5 to 100 μm, and particularly 10 to 5
It is desirable to be in the range of 0 μm.

【0040】[0040]

【実施例】以下に、実施例に基づき、本発明をより詳細
に説明する。 電荷発生剤 I:X型フリーメタルフタロシアニン(Ip=5.38
eV) II:オキソチタニルフタロシアニン(Ip=5.32e
V) III :1,4−ジチオケト−3,6−ジフェニル−ピロ
ロ−[3,4−C]ピロロピロール(Ip=5.46e
V) IV:N,N−ビス(3,5−ジメチルフェニル)−ペリ
レン−3,4,9,10−テトラカルボキシルジイミド
(Ip=5.60eV) 正孔輸送剤 4Me−TPD 6Me−TPD 電子輸送剤 a:テトラクロロ−p−ベンゾキノン (還元電位
−0.30V) b:テトラブロモ−p−ベンゾキノン (還元電位
−0.30V) c:2,5−ジクロロ−p−ベンゾキノン(還元電位
−0.51V) d:2,6−ジクロロ−p−ベンゾキノン(還元電位
−0.51V) e:p−ベンゾキノン (還元電位
−0.81V) f:テトラメチル−p−ベンゾキノン (還元電位
−1.20V) g:2,6−ジタ−シャルブチル−p−ベンゾキノン
(還元電位 −1.30V)
EXAMPLES The present invention will be described in more detail based on the following examples. Charge Generating Agent I: X-type Free Metal Phthalocyanine (Ip = 5.38)
eV) II: oxotitanyl phthalocyanine (Ip = 5.32e)
V) III: 1,4-dithioketo-3,6-diphenyl-pyrrolo- [3,4-C] pyrrolopyrrole (Ip = 5.46e
V) IV: N, N-bis (3,5-dimethylphenyl) -perylene-3,4,9,10-tetracarboxyldiimide (Ip = 5.60 eV) hole transport agent 4Me-TPD 6Me-TPD electron transport Agent a: tetrachloro-p-benzoquinone (reduction potential
-0.30 V) b: tetrabromo-p-benzoquinone (reduction potential
-0.30 V) c: 2,5-dichloro-p-benzoquinone (reduction potential
-0.51V) d: 2,6-dichloro-p-benzoquinone (reduction potential
-0.51V) e: p-benzoquinone (reduction potential
-0.81V) f: tetramethyl-p-benzoquinone (reduction potential
-1.20 V) g: 2,6-di-tert-butyl-p-benzoquinone (reduction potential -1.30 V)

【0041】還元電位測定方法 測定溶液として、電解質(過塩素酸tert−ブチルア
ンモニウム)0.1mol、測定物(各電子輸送剤)
0.1mol、溶剤(ジクロロメタン)1リットルを調合し
て、3電極式〔作用電極・グラッシーカーボン電極、対
極・白金電極、参照電極・銀−硝酸銀電極(0.1mo
l/リットル AgNO3 −アセトニトリル溶液)〕のサイ
クリックボルターメトリーにて測定を行ない、得られた
測定データーにより酸化還元電位を求めた。
Method for measuring reduction potential As a measuring solution, 0.1 mol of electrolyte (tert-butylammonium perchlorate), a substance to be measured (each electron transfer agent)
0.1 mol and 1 liter of solvent (dichloromethane) were mixed to prepare a three-electrode type [working electrode / glassy carbon electrode, counter electrode / platinum electrode, reference electrode / silver-silver nitrate electrode (0.1 mo
1 / L AgNO 3 -acetonitrile solution)] was measured by cyclic voltammetry, and the redox potential was determined from the obtained measurement data.

【0042】実施例1〜3、比較例1〜4 電荷発生剤として、表1に示す化合物1重量部、正孔輸
送剤として表1に示す化合物70重量部、電子輸送剤と
して表1に示すベンゾキノン誘導体30重量部、バイン
ダーとしてのポリカーボネイト100重量部及び溶剤と
しての所定量のジクロロメタンをボールミルで混合分散
し単層型感光層塗布液を調製し、この調製液をアルミニ
ウム箔上にワイヤーバーにて塗布した後、60℃で60
分間熱風乾燥することにより膜厚15〜20μmの単層
型電子写真用感光体を作製した。
Examples 1 to 3 and Comparative Examples 1 to 4 1 part by weight of the compound shown in Table 1 as a charge generating agent, 70 parts by weight of the compound shown in Table 1 as a hole transferring material, and Table 1 as an electron transferring material. 30 parts by weight of a benzoquinone derivative, 100 parts by weight of polycarbonate as a binder and a predetermined amount of dichloromethane as a solvent were mixed and dispersed by a ball mill to prepare a single layer type photosensitive layer coating solution, and the prepared solution was coated on an aluminum foil with a wire bar. After coating, 60 at 60 ℃
A single-layer type electrophotographic photoreceptor having a film thickness of 15 to 20 μm was produced by drying with hot air for a minute.

【0043】比較例5 電子輸送剤を加えずに実施例1〜3と同様に感光体を作
製した。
Comparative Example 5 A photoconductor was prepared in the same manner as in Examples 1 to 3 without adding an electron transfer agent.

【0044】実施例4〜5、比較例6 実施例1〜3及び比較例5で得られた電子写真用感光体
を負帯電にて評価を行った。
Examples 4 to 5 and Comparative Example 6 The electrophotographic photoconductors obtained in Examples 1 to 3 and Comparative Example 5 were evaluated by negative charging.

【0045】実施例6〜9 電荷発生剤を5重量部とした以外は実施例1〜3と同様
にして感光体を作製した。
Examples 6 to 9 Photoreceptors were prepared in the same manner as in Examples 1 to 3 except that the charge generating agent was 5 parts by weight.

【0046】実施例10〜12 電荷発生剤を10重量部とした以外は実施例1〜3と同
様にして感光体を作製した。
Examples 10 to 12 Photosensitive members were prepared in the same manner as in Examples 1 to 3 except that the charge generating agent was changed to 10 parts by weight.

【0047】実施例13〜15 正孔輸送剤を10重量部とした以外は実施例1〜3と同
様にして感光体を作製した。
Examples 13 to 15 Photoreceptors were prepared in the same manner as in Examples 1 to 3 except that 10 parts by weight of the hole transfer material was used.

【0048】実施例16〜18 正孔輸送剤を80重量部とした以外は実施例1〜3と同
様にして感光体を作製した。
Examples 16 to 18 Photosensitive members were prepared in the same manner as in Examples 1 to 3 except that the amount of the hole transfer material was 80 parts by weight.

【0049】実施例19〜21 電子輸送剤を10重量部とした以外は実施例1〜3と同
様にして感光体を作製した。
Examples 19 to 21 Photoreceptors were prepared in the same manner as in Examples 1 to 3 except that the electron transfer agent was changed to 10 parts by weight.

【0050】実施例22〜24 電子輸送剤を50重量部とした以外は実施例1〜3と同
様にして感光体を作製した。
Examples 22 to 24 Photoreceptors were prepared in the same manner as in Examples 1 to 3 except that 50 parts by weight of the electron transfer agent was used.

【0051】実施例25〜27 感光体膜厚を10μmとした以外は実施例1〜3と同様
にして感光体を作製した。
Examples 25 to 27 Photosensitive members were prepared in the same manner as in Examples 1 to 3 except that the film thickness of the photosensitive member was 10 μm.

【0052】実施例28〜30 感光体膜厚を30μmとした以外は実施例1〜3と同様
にして感光体を作製した。
Examples 28 to 30 Photosensitive members were prepared in the same manner as in Examples 1 to 3 except that the film thickness of the photosensitive member was 30 μm.

【0053】実施例31〜33 正孔輸送剤を表2に示す化合物に変えること以外は実施
例1〜3と同様にして感光体を作製した。
Examples 31 to 33 Photoreceptors were prepared in the same manner as in Examples 1 to 3 except that the compounds shown in Table 2 were used instead of the hole transfer agent.

【0054】実施例34〜42 電荷発生剤を表2に示す化合物に変えること以外は実施
例1〜3と同様にして感光体を作製した。
Examples 34 to 42 Photoreceptors were prepared in the same manner as in Examples 1 to 3 except that the compounds shown in Table 2 were used as the charge generating agent.

【0055】電子写真感光体の評価 静電複写試験装置(川口電気社製、EPA−8100)
を用いて、各実施例で得られた感光体に印加電圧を加
え、正または負に帯電させ、光源として白色ハロゲン光
を用いて電子写真特性を測定し、その結果を表1及び表
2に示した。表中のV1は電圧を印加して感光体を帯電
させたときの感光体の初期表面電位を示し、また、V2
は露光開始後1秒経過後の表面電位を残留電位として測
定したものであり、コントラスト電位は、V1とV2の
差である。
Evaluation of Electrophotographic Photosensitive Member Electrostatic copying tester (EPA-8100, manufactured by Kawaguchi Electric Co., Ltd.)
By applying an applied voltage to the photoconductor obtained in each of the examples to charge it positively or negatively, and the electrophotographic characteristics were measured using white halogen light as a light source. The results are shown in Tables 1 and 2. Indicated. V1 in the table indicates the initial surface potential of the photoconductor when the photoconductor is charged by applying a voltage, and V2
Is measured as the residual potential after 1 second has elapsed from the start of exposure, and the contrast potential is the difference between V1 and V2.

【0056】[0056]

【表1】 [Table 1]

【0057】[0057]

【表2】 [Table 2]

【0058】表1及び表2より明らかなように電子輸送
剤として還元電位が−0.8V〜−1.8Vの範囲のベ
ンゾキノン誘導体を含有した本発明の電子写真感光体
は、残留電位の低下したものであった。これに対して、
還元電位が−0.8V〜−1.8Vの範囲を外れたベン
ゾキノン誘導体を含有した比較例1〜4の電子写真感光
体及びベンゾキノン誘導体を含有しない比較例5〜6の
電子写真感光体は、残留電位の上昇したものであった。
As is clear from Tables 1 and 2, the electrophotographic photoreceptor of the present invention containing a benzoquinone derivative having a reduction potential in the range of -0.8 V to -1.8 V as an electron transfer agent has a reduced residual potential. It was something that was done. On the contrary,
The electrophotographic photoreceptors of Comparative Examples 1 to 4 containing a benzoquinone derivative having a reduction potential outside the range of −0.8 V to −1.8 V and the electrophotographic photoreceptors of Comparative Examples 5 to 6 not containing a benzoquinone derivative, The residual potential was increased.

【0059】[0059]

【発明の効果】本発明によれば、電子輸送剤として還元
電位が−0.8V〜−1.3Vのベンゾキノン誘導体を
選択し、これを正孔輸送剤と組合せ、電荷発生剤と共に
樹脂媒質中に分散させて、単層分散型有機感光体とする
ことにより、感光体の残留電位を低下させ、感度を向上
させることができた。この感光体は正帯電及び両帯電の
用途に使用でき、特にデジタル電子写真の用途に有用で
ある。
According to the present invention, a benzoquinone derivative having a reduction potential of -0.8 V to -1.3 V is selected as an electron transfer agent, and this is combined with a hole transfer agent, and is combined with a charge generating agent in a resin medium. It was possible to lower the residual potential of the photoconductor and improve the sensitivity by dispersing it into a single layer dispersion type organic photoconductor. This photoreceptor can be used for positive charging and dual charging, and is particularly useful for digital electrophotography.

【図面の簡単な説明】[Brief description of drawings]

【図1】 電荷発生剤、正孔輸送剤及び種々のベンゾキ
ノン類を一定の量比で含んだ単層分散型有機感光体のベ
ンゾキノン類の還元電位と残留電位コントラストとの関
係をプロットした図
FIG. 1 is a graph plotting the relationship between the reduction potential of benzoquinones and the residual potential contrast of a monolayer dispersion type organic photoconductor containing a charge generating agent, a hole transporting agent and various benzoquinones in a fixed amount ratio.

【図2】 本発明の電子写真用有機感光体を示す図FIG. 2 is a diagram showing an organic photoconductor for electrophotography of the present invention.

【符号の説明】[Explanation of symbols]

1 導電性基体 2 有機感光体層 CG 電荷発生剤 HT 正孔輸送剤 ET 電子輸送剤 1 Conductive Substrate 2 Organic Photoreceptor Layer CG Charge Generating Agent HT Hole Transporting Agent ET Electron Transporting Agent

───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.5 識別記号 庁内整理番号 FI 技術表示箇所 G03G 5/06 372 8305−2H ─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. 5 Identification code Office reference number FI technical display location G03G 5/06 372 8305-2H

Claims (7)

【特許請求の範囲】[Claims] 【請求項1】 導電性基体上に有機感光層を設けた電子
写真用有機感光体において、有機感光層が樹脂媒質中に
分散された電荷発生剤、正孔輸送剤および電子輸送剤と
しての還元電位が−0.8〜−1.3Vのベンゾキノン
誘導体から成る組成物である有機感光体。
1. An organic photoreceptor for electrophotography comprising an organic photosensitive layer on a conductive substrate, wherein the organic photosensitive layer is dispersed in a resin medium as a charge generating agent, a hole transfer agent and an electron transfer agent. An organophotoreceptor which is a composition comprising a benzoquinone derivative having a potential of -0.8 to -1.3V.
【請求項2】 ベンゾキノン誘導体が式 【化1】 式中、R1,R2,R3及びR4は少なくとも1個がアルキ
ル基、アルコキシ基またはアミノ基等の電子供与性基で
あるという条件下に水素原子または電子供与性基である
で表わされる化合物である請求項1記載の有機感光体。
2. A benzoquinone derivative is represented by the formula: In the formula, R1, R2, R3 and R4 are compounds represented by hydrogen atom or electron donating group under the condition that at least one is electron donating group such as alkyl group, alkoxy group or amino group. The organic photoreceptor according to claim 1.
【請求項3】 電荷発生剤が5.3乃至5.6eVのイ
オン化ポテンシャルを有する電荷発生剤である請求項1
記載の有機感光体。
3. The charge generating agent is a charge generating agent having an ionization potential of 5.3 to 5.6 eV.
The organic photoreceptor described.
【請求項4】 電荷発生剤がX型無金属フタロシアニン
である請求項1記載の有機感光体。
4. The organophotoreceptor according to claim 1, wherein the charge generating agent is an X-type metal-free phthalocyanine.
【請求項5】 正孔輸送剤が5.3乃至5.6eVのイ
オン化ポテンシャルを有する正孔輸送剤である請求項1
記載の有機感光体。
5. The hole transferring material is a hole transferring material having an ionization potential of 5.3 to 5.6 eV.
The organic photoreceptor described.
【請求項6】 正孔輸送剤がアルキル置換トリフェニル
ジアミン誘導体である、請求項1記載の有機感光体。
6. The organophotoreceptor according to claim 1, wherein the hole transporting agent is an alkyl-substituted triphenyldiamine derivative.
【請求項7】 結着樹脂に対し電荷発生剤が1.0乃至
10重量%、正孔輸送剤が10乃至80重量%及び電子
輸送剤が10乃至40重量%の量で夫々存在する請求項
1記載の有機感光体。
7. The charge generating agent is present in an amount of 1.0 to 10% by weight, the hole transfer agent is in an amount of 10 to 80% by weight, and the electron transfer agent is in an amount of 10 to 40% by weight, based on the binder resin. 1. The organic photoreceptor according to 1.
JP3207899A 1991-08-20 1991-08-20 Electrophotographic organic sensitive body Pending JPH0545908A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP3207899A JPH0545908A (en) 1991-08-20 1991-08-20 Electrophotographic organic sensitive body

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP3207899A JPH0545908A (en) 1991-08-20 1991-08-20 Electrophotographic organic sensitive body

Publications (1)

Publication Number Publication Date
JPH0545908A true JPH0545908A (en) 1993-02-26

Family

ID=16547421

Family Applications (1)

Application Number Title Priority Date Filing Date
JP3207899A Pending JPH0545908A (en) 1991-08-20 1991-08-20 Electrophotographic organic sensitive body

Country Status (1)

Country Link
JP (1) JPH0545908A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH08248656A (en) * 1995-03-08 1996-09-27 Mita Ind Co Ltd Electrophotographic photosensitive material
JP2012208231A (en) * 2011-03-29 2012-10-25 Kyocera Document Solutions Inc Positively-charged single-layered electrophotographic photoreceptor, and image forming apparatus

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH08248656A (en) * 1995-03-08 1996-09-27 Mita Ind Co Ltd Electrophotographic photosensitive material
JP2012208231A (en) * 2011-03-29 2012-10-25 Kyocera Document Solutions Inc Positively-charged single-layered electrophotographic photoreceptor, and image forming apparatus

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