JP5582390B2 - Electrophotographic photosensitive member, electrophotographic method, electrophotographic apparatus, and process cartridge for electrophotographic apparatus - Google Patents

Description

The present invention relates to an electrophotographic photosensitive member containing at least one specific pyromellitic diimide-isoindole dimer derivative in the photosensitive layer, and an electrophotographic method, an electrophotographic apparatus using the electrophotographic photosensitive member, The present invention relates to an electrophotographic process cartridge.

In recent years, there has been a remarkable development in information processing system machines using electrophotography.
In particular, laser printers and digital copying machines that convert information into digital signals and record information with light have significantly improved print quality and reliability. Furthermore, they have been applied to laser printers or digital copiers capable of full-color printing by merging with high-speed technology. From such a background, it is particularly important to achieve both high image quality and high durability as a required photoreceptor function.

  As photoconductors used in these electrophotographic laser printers, digital copiers, etc., those using organic photosensitive materials (OPC) are generally widely used for reasons such as cost, productivity and non-pollution. Applied. The layer structure of the OPC photoreceptor is roughly divided into a single layer type and a function separation type laminated structure. The first practical OPC, the PVK-TNF charge transfer complex type photoreceptor, was the former single layer type.

On the other hand, in 1968, Hayashi and Regensburger independently invented a PVK / a-Se laminated photoreceptor, and later in 1977 by Melz et al. And in 1978 Schlosser called an organic pigment dispersion layer and an organic low molecular dispersion polymer layer. A multi-layer photoconductor in which all photosensitive layers are made of organic materials has been announced. These are functionally separated from the concept of a charge generation layer (CGL) that absorbs light and generates charges, and a charge transport layer (CTL) that injects and transports charges generated by CGL and neutralizes surface charges. Also called a mold-laminated photoconductor.
However, organic photoconductors have larger film scraping due to repeated use than inorganic ones. If the photoconductive layer is further scraped off, the surface of the photoconductor is deteriorated due to a decrease in charge potential, photosensitivity, or scratches on the surface of the photoconductor. There is a strong tendency to promote dirt, image density reduction or image quality degradation. Therefore, the wear resistance of organic photoreceptors has been cited as a major problem. Further, in recent years, with the increase in the speed of an electrophotographic apparatus or the reduction in the diameter of the photoreceptor accompanying the downsizing of the apparatus, it has become a more important issue to improve the durability of the photoreceptor.

As a method for improving the abrasion resistance of the photosensitive member, a method of imparting lubricity to the photosensitive layer, curing the photosensitive layer, containing a filler, or a low molecular charge transport material (CTM) molecular dispersed polymer layer Instead of this, a method using a polymer charge transport material is widely known.
However, a new problem arises when the abrasion of the photosensitive layer is suppressed by these methods.
That is, ozone, NOx, and other oxidizing substances that are repeatedly used on the surface of the photosensitive layer and adsorbed by the surrounding environment are adsorbed. Depending on the repeated use and use environment, the resistance of the outermost surface is lowered, and image flow (image blur), etc. Known to cause problems. Conventionally, the problem has been avoided to some extent by removing the blur generating material little by little together with the photosensitive layer.

However, as described above, in order to meet the recent demand for higher resolution and higher durability, a new method has to be applied.
One method of reducing these effects is to mount a heater on the photoreceptor, which is a major obstacle to downsizing the apparatus and reducing power consumption. Additives such as antioxidants are also effective means, but mere additives are those that do not have photoconductivity. Therefore, addition of a large amount to the photosensitive layer can reduce the sensitivity and increase the residual potential. It will imitate the problem of photographic characteristics.

As described above, electrophotographic photoconductors with high wear resistance or reduced shaving due to the process design around the photoconductor avoid the effects on image quality such as image blurring and reduced resolution as side effects. Thus, it has been difficult to achieve both high durability and high image quality. This is because a higher resistance is suitable for suppressing the occurrence of image blur, and a lower resistance is suitable for suppressing the increase in residual potential. It is difficult to solve.
Most of the electrophotographic photoreceptors in practical use are function-separated type electrophotographic photoreceptors in which a charge generation layer and a charge transport layer are laminated on a conductive substrate, and charge transport materials contained in the charge transport layer are as follows. A hole transport material is used. These are used exclusively for negatively charged electrophotographic processes.

In addition, a highly reliable charging method in the electrophotographic process is based on corona discharge, and this method is adopted in most copying machines and printers.
However, as is well known, the negative corona discharge is unstable compared to the positive polarity, and for this reason, a scorotron charging method is adopted, which is a factor in increasing costs. The negative corona discharge is accompanied by a larger amount of ozone, a substance that causes chemical damage. Therefore, it is generated during the long-term oxidative degradation of the binder resin and charge transfer material due to ozone generated during charging, and is generated during charging. As a result, accumulation of ionic compounds such as nitrogen oxide ions, sulfur oxide ions, ammonium ions, etc. on the surface of the photoconductor causes a decrease in image quality, which is a problem. For this reason, ozone filters are often used in negatively charged copying machines and printers in order to prevent ozone from being discharged to the outside, which also increases the cost of the apparatus. Also, a large amount of ozone is a problem of environmental pollution.

In order to solve these problems, development of a positively charged electrophotographic photosensitive member is underway.
If the positive charging method is used, the generation amount of ozone, nitrogen oxide ions, etc. is suppressed, and the use of a two-component developer that is widely used at present makes the electrophotographic photosensitive member positively charged. A stable image with little environmental fluctuation can be obtained. From this aspect, a positively charged electrophotographic photosensitive member is desirable.
However, positively charged single-layer and reverse-layer photoconductors have a charge generating material that is very sensitive to oxidizing substances such as ozone and nitrogen oxide ions in the vicinity of the surface. For example, there is a drawback that the characteristic fluctuation due to the exhaust gas from a blue heater or a car is large.

  On the other hand, in the case of a high-speed copying process, it is preferable to use a negative charging type rather than a positive charging type as described above. The reason for this is that most organic materials exhibiting a high charge mobility that does not hinder high-speed copying processes, etc. are currently limited to hole transport materials having only the property of hole transfer. This is because, in a forward layered electrophotographic photosensitive member in which a charge transporting layer formed using a hole transporting material is arranged on the surface side, the charging property is limited to negative charging on the principle of operation.

  As described above, regarding the charging polarity, if the electrophotographic photosensitive member can be used in both positive and negative polarities, the application range of the photosensitive member can be further expanded, and the cost can be reduced by reducing the number of photosensitive members. This is advantageous for speeding up.

  Under such circumstances, an electrophotographic photosensitive member capable of being charged in both polarities is disclosed in Japanese Patent No. 2732697 of Patent Document 1, but the diphenoquinone derivative of the electron transport material used here has a slight charge mobility. For this reason, the photoconductor sensitivity characteristics are not sufficient when considering high speed and downsizing of copying machines and printers, and there is a disadvantage that image blur is caused by repeated use.

  Japanese Patent Application Laid-Open No. 2000-231204 of Patent Document 2 discloses an aromatic compound having a dialkylamino group as an acid scavenger on a photoreceptor. This compound is effective for image quality after repeated use. However, since the charge transport ability is low, it is difficult to meet demands for high sensitivity and high speed, and there is a limit in the amount of addition.

Furthermore, stilbene compounds having a dialkylamino group disclosed in JP-A-60-196768 of Patent Document 3 and Japanese Patent No. 2884353 of Patent Document 4 are also effective against image blur due to oxidation-resistant gas. [Non-Patent Document 1 (Itami et al., Konica Technical Report, Vol. 13, p. 37, 2000)].
However, since this has a dialkylamino group that is a substituent of a strong mesomeric effect (+ M effect) at the resonance site of the triarylamine structure that is a charge transport site, the overall ionization potential value becomes abnormally small. Therefore, the charge retention ability of the photosensitive layer used alone as a hole transporting material is remarkably deteriorated from the beginning or by repeated use. Even when mixed with substances, the ionization potential values of the above stilbene compounds are much smaller than those, so the stilbene compounds become hole trap sites for mobile charges, resulting in an electrophotographic photosensitive member with significantly low sensitivity and a large residual potential. End up.

Japanese Patent Application Laid-Open No. 2004-258253 of Patent Document 5 proposes a photoconductor that includes a stilbene compound and a specific diamine compound, can be used repeatedly without causing a decrease in sensitivity, and has improved environmental resistance to acid gas and the like. Has been.
However, it is not yet sufficient to realize downsizing of the apparatus accompanying high-speed printing or reduction in the diameter of the photoreceptor.

On the other hand, in the pyromellitic acid diimide-isoindole dimer derivative, the synthesis method of 1,3-diphenyl-2-phthalimidoisoindole is a non-patent document 2 of DW Jones, Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic. Chemistry, 21, 2728 (1972), but it is not suggested to be used for an electrophotographic photoreceptor.

An object of the present invention is to provide an electrophotographic photosensitive material that has high durability even for repeated use over a long period of time, suppresses image deterioration due to image density reduction or image blurring, and stably obtains high-quality images. To provide a body.
In addition, it is possible to obtain photoconductors that are charged to either positive or negative polarity, and by using these photoconductors, it is not necessary to replace the photoconductors, and it is possible to reduce the size of the apparatus due to high-speed printing or reduction in the diameter of the photoconductor. Another object of the present invention is to provide an electrophotographic method, an electrophotographic apparatus, and an electrophotographic process cartridge that can be realized and can stably obtain a high-quality image even in repeated use.

The said subject is solved by (1)-(19) in this invention.
(1) “An electrophotographic photoreceptor having at least a photosensitive layer provided on a conductive support, wherein the photosensitive layer contains a pyromellitic acid diimide-isoindole dimer derivative represented by the following general formula (1): An electrophotographic photosensitive member characterized by comprising:

［式中、Ｒ１、Ｒ２、Ｒ３、Ｒ４、Ｒ５、Ｒ６、Ｒ７は水素原子、置換もしくは無置換のアルキル基、アルコキシ基、置換もしくは無置換の芳香族炭化水素基、ハロゲン原子、ニトロ基を表わし、それぞれ同一でも異なっていてもよい。また、ｉ、ｊは１〜４の整数を、ｋ、ｌ、ｍ、ｎは１〜５の整数を、ｏは１または２の整数を表わす。］」、
（２）「正および負のいずれの極性にも帯電することを特徴とする前記第（１）項記載の電子写真感光体。」、
（３）「前記感光層は、電荷輸送物質をさらに含むものであることを特徴とする前記第（１）項又は第（２）項記載の電子写真感光体。」、
（４）「前記電荷輸送物質が下記一般式（２）で表わされる誘導体であることを特徴とする前記第（３）項に記載の電子写真感光体。

[Wherein R1, R2, R3, R4, R5, R6, R7 represent a hydrogen atom, a substituted or unsubstituted alkyl group, an alkoxy group, a substituted or unsubstituted aromatic hydrocarbon group, a halogen atom, or a nitro group. These may be the same or different. I and j are integers of 1 to 4, k, l, m, and n are integers of 1 to 5, and o is an integer of 1 or 2. ] ",
(2) “The electrophotographic photosensitive member according to the item (1), which is charged to both positive and negative polarities”.
(3) "The electrophotographic photosensitive member according to (1) or (2) above, wherein the photosensitive layer further contains a charge transport material",
(4) The electrophotographic photosensitive member according to item (3), wherein the charge transport material is a derivative represented by the following general formula (2).

［式中、Ｘは単結合もしくはビニレン基を表わし、Ｒ４は水素原子、置換もしくは無置換のアルキル基、または置換もしくは無置換の芳香族炭化水素基を表わし、Ａｒ１は置換もしくは無置換の芳香族炭化水素基を表わし、Ｒ５は水素原子、置換もしくは無置換のアルキル基、あるいは置換もしくは無置換の芳香族炭化水素基を表わし、Ａｒ１とＲ５は共同で環を形成してもよい。Ａは一般式（３）、一般式（４）、９−アントリル基または置換もしくは無置換のカルバゾリル基を表わす。

[Wherein, X represents a single bond or a vinylene group, R 4 represents a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aromatic hydrocarbon group, and Ar 1 represents a substituted or unsubstituted aromatic group. Represents a hydrocarbon group, R5 represents a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aromatic hydrocarbon group, and Ar1 and R5 may form a ring together. A represents general formula (3), general formula (4), a 9-anthryl group, or a substituted or unsubstituted carbazolyl group.

（ここでＲ６は水素原子、アルキル基、アルコキシ基、ハロゲン原子または一般式（５）を表わす。）

(Here, R6 represents a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, or general formula (5).)

（ただし、Ｒ７およびＲ８は置換もしくは無置換のアルキル基、置換もしくは無置換の芳香族炭化水素基を示し、Ｒ７およびＲ８は同じでも異なっていてもよく、環を形成してもよい）を表わし、ｍは１〜３の整数を表わし、２以上のときＲ６は同一でも異なってもよい。］」、
（５）「前記電荷輸送物質が下記一般式（６）で表わされる誘導体であることを特徴とする前記第（３）項に記載の電子写真感光体。

Wherein R7 and R8 represent a substituted or unsubstituted alkyl group or a substituted or unsubstituted aromatic hydrocarbon group, and R7 and R8 may be the same or different and may form a ring. , M represents an integer of 1 to 3, and when it is 2 or more, R6 may be the same or different. ] ",
(5) The electrophotographic photosensitive member according to item (3), wherein the charge transport material is a derivative represented by the following general formula (6).

［式中、Ｒ９、Ｒ１１およびＲ１２は水素原子、アミノ基、アルコキシ基、チオアルコキシ基、アリールオキシ基、メチレンジオキシ基、置換もしくは無置換のアルキル基、ハロゲン原子または置換もしくは無置換の芳香族炭化水素基を、Ｒ１０は水素原子、アルコキシ基、置換もしくは無置換のアルキル基またはハロゲン原子を表わす。また、ｋ、ｌ、ｍおよびｎは１、２、３または４の整数であり、それぞれが２、３または４の整数のときは、前記Ｒ９、Ｒ１０、Ｒ１１およびＲ１２は同じでも異なっていてもよい。］」、
（６）「前記電荷輸送物質が下記一般式（７）で表わされる誘導体であることを特徴とする前記第（３）項に記載の電子写真感光体。

[Wherein R9, R11 and R12 are a hydrogen atom, an amino group, an alkoxy group, a thioalkoxy group, an aryloxy group, a methylenedioxy group, a substituted or unsubstituted alkyl group, a halogen atom or a substituted or unsubstituted aromatic group. In the hydrocarbon group, R10 represents a hydrogen atom, an alkoxy group, a substituted or unsubstituted alkyl group or a halogen atom. K, l, m and n are integers of 1, 2, 3 or 4, and when each is an integer of 2, 3 or 4, R9, R10, R11 and R12 may be the same or different. Good. ] ",
(6) The electrophotographic photosensitive member according to item (3), wherein the charge transport material is a derivative represented by the following general formula (7).

［式中、Ｘは単結合もしくはビニレン基を表わし、Ｒ１３、Ｒ１４は水素原子、置換もしくは無置換のアルキル基または置換もしくは無置換の芳香族炭化水素基を表わし、Ａｒ３は置換もしくは無置換の芳香族炭化水素基を表わし、Ａｒ３とＲ１３は共同で環を形成してもよい。Ａｒ２は下記一般式（８）または一般式（９）を表わす。

[Wherein, X represents a single bond or a vinylene group, R13 and R14 represent a hydrogen atom, a substituted or unsubstituted alkyl group or a substituted or unsubstituted aromatic hydrocarbon group, and Ar3 represents a substituted or unsubstituted aromatic group. Represents a group hydrocarbon group, Ar 3 and R 13 may form a ring together. Ar2 represents the following general formula (8) or general formula (9).

（ここでＲ６は水素原子、アルキル基、アルコキシ基、ハロゲン原子を表わし、ｍは１〜３の整数を表わし、２以上のときＲ６は同一でも異なってもよい。またＲ７は置換もしくは無置換のアルキル基、または置換もしくは無置換の芳香族炭化水素基を表わす。）］」、
（７）「前記電荷輸送物質が下記一般式（１０）で表わされる誘導体であることを特徴とする前記第（３）項に記載の電子写真感光体。

(Here, R6 represents a hydrogen atom, an alkyl group, an alkoxy group, or a halogen atom, m represents an integer of 1 to 3, and when R2 is 2 or more, R6 may be the same or different. R7 may be substituted or unsubstituted. Represents an alkyl group or a substituted or unsubstituted aromatic hydrocarbon group.
(7) The electrophotographic photosensitive member according to item (3), wherein the charge transport material is a derivative represented by the following general formula (10).

［式中、Ｘは単結合もしくはビニレン基を表わし、Ｒ１５、Ｒ１６は水素原子、置換もしくは無置換のアルキル基または置換もしくは無置換の芳香族炭化水素基を表わし、Ａｒ４は置換もしくは無置換の２価の芳香族炭化水素基を表わし、Ａは一般式（３）、一般式（４）、９−アントリル基または置換もしくは無置換のカルバゾリル基を表わす。

[Wherein, X represents a single bond or a vinylene group, R15 and R16 represent a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aromatic hydrocarbon group, and Ar4 represents a substituted or unsubstituted 2 group. Represents a divalent aromatic hydrocarbon group, and A represents a general formula (3), a general formula (4), a 9-anthryl group, or a substituted or unsubstituted carbazolyl group.

（ここでＲ６は水素原子、アルキル基、アルコキシ基、ハロゲン原子または一般式（５）を表わす。）

(Here, R6 represents a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, or general formula (5).)

（ただし、Ｒ７およびＲ８は置換もしくは無置換のアルキル基、置換もしくは無置換の芳香族炭化水素基を示し、Ｒ７およびＲ８は同じでも異なっていてもよく、環を形成してもよい）を表わし、ｍは１〜３の整数を表わし、２以上のときＲは同一でも異なってもよい。］」、
（８）「前記電荷輸送物質が下記一般式（１４）で表わされる誘導体であることを特徴とする前記第（３）項に記載の電子写真感光体。

Wherein R7 and R8 represent a substituted or unsubstituted alkyl group or a substituted or unsubstituted aromatic hydrocarbon group, and R7 and R8 may be the same or different and may form a ring. , M represents an integer of 1 to 3, and when 2 or more, R may be the same or different. ] ",
(8) The electrophotographic photosensitive member according to item (3), wherein the charge transport material is a derivative represented by the following general formula (14).

（式中、Ｒ１７、Ｒ１８は水素原子、置換もしくは無置換のアルキル基、置換もしくは無置換の芳香族炭化水素基を表わし、それぞれ同じでも異なっていてもよい。）」、
（９）「前記電荷輸送物質が下記一般式（１５）で表わされる誘導体であることを特徴とする前記第（３）項に記載の電子写真感光体。

(Wherein R17 and R18 represent a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aromatic hydrocarbon group, which may be the same or different from each other). "
(9) The electrophotographic photosensitive member according to item (3), wherein the charge transport material is a derivative represented by the following general formula (15).

〔式中、Ｒ１９は置換基を有してもよいアルキル基、または置換基を有してもよいアリール基を示し、Ｒ２０は置換基を有してもよいアルキル基、置換基を有してもよい芳香族炭化水素基、または下記式一般式（１６）で表わされる基を示す。

[Wherein R19 represents an alkyl group which may have a substituent or an aryl group which may have a substituent, and R20 has an alkyl group which may have a substituent or a substituent. Or a group represented by the following general formula (16):

（式中、Ｒ２１は、置換基を有してもよいアルキル基、または置換基を有してもよいアリール基を示す。）」、
（１０）「前記電荷輸送物質が下記一般式（１７）で表わされる誘導体であることを特徴とする前記第（３）項に記載の電子写真感光体。

(Wherein R21 represents an alkyl group which may have a substituent, or an aryl group which may have a substituent).
(10) The electrophotographic photosensitive member according to item (3), wherein the charge transport material is a derivative represented by the following general formula (17).

（式中Ｒ２２、Ｒ２３は水素原子、置換もしくは無置換のアルキル基、置換もしくは無置換の芳香族炭化水素基を表わし、それぞれ同じでも異なっていてもよい。）」、
（１１）「前記電荷輸送物質が下記一般式（１８）で表わされる誘導体であることを特徴とする前記第（３）項に記載の電子写真感光体。

(Wherein R22 and R23 represent a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aromatic hydrocarbon group, which may be the same or different from each other).
(11) The electrophotographic photosensitive member according to item (3), wherein the charge transport material is a derivative represented by the following general formula (18).

（式中、Ｒ２４、Ｒ２５は水素原子、置換もしくは無置換のアルキル基、置換もしくは無置換の芳香族炭化水素基を表わし、それぞれ同じでも異なっていてもよい。）」、
（１２）「前記感光層は、少なくとも電荷発生層、電荷輸送層を順次積層したものであることを特徴とする前記第（１）項乃至第（１１）項のいずれかに記載の電子写真感光体。」、
（１３）「前記感光層は、少なくとも電荷輸送層、電荷発生層を順次積層したものであることを特徴とする前記第（１）項乃至第（１１）項のいずれかに記載の電子写真感光体。」、
（１４）「前記感光層は、単層型の感光層であることを特徴とする前記第（１）項乃至第（１３）項のいずれかに記載の電子写真感光体。」、
（１５）「電子写真感光体に、少なくとも帯電、画像露光、現像、転写が繰り返し行なわれる電子写真方法であって、該電子写真感光体は前記第（１）項乃至第（１４）項のいずれかに記載の電子写真感光体であることを特徴とする電子写真方法。」、
（１６）「電子写真感光体に、少なくとも帯電、画像露光、現像、転写を繰り返し行ない、かつ画像露光の際にはＬＤあるいはＬＥＤ等によって感光体上に静電潜像の書き込みが行なわれる、デジタル方式の電子写真方法であって、該電子写真感光体は前記第（１）項乃至第（１４）項のいずれかに記載の電子写真感光体であることを特徴とする電子写真方法。」、
（１７）「少なくとも帯電手段、画像露光手段、現像手段、転写手段および電子写真感光体を具備してなる電子写真装置であって、該電子写真感光体は前記第（１）項乃至第（１４）項のいずれかに記載の電子写真感光体であることを特徴とする電子写真装置。」、
（１８）「少なくとも帯電手段、画像露光手段、現像手段、転写手段および電子写真感光体を具備してなる電子写真装置であって、画像露光手段にＬＤあるいはＬＥＤ等を使用することによって感光体上に静電潜像の書き込みが行なわれる、デジタル方式の電子写真装置であって、該電子写真感光体は前記第（１）項乃至第（１４）項のいずれかに記載の電子写真感光体であることを特徴とする電子写真装置。」、
（１９）「少なくとも電子写真感光体を具備してなる電子写真装置用プロセスカートリッジであって、該電子写真感光体は前記第（１）項乃至第（１４）項のいずれかに記載の電子写真感光体であることを特徴とする電子写真装置用プロセスカートリッジ。」。

(Wherein R24 and R25 each represents a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aromatic hydrocarbon group, which may be the same or different from each other). "
(12) "The electrophotographic photosensitive member according to any one of items (1) to (11), wherein the photosensitive layer is formed by sequentially laminating at least a charge generation layer and a charge transport layer. body.",
(13) The electrophotographic photosensitive member according to any one of items (1) to (11), wherein the photosensitive layer is a layer in which at least a charge transport layer and a charge generation layer are sequentially laminated. body.",
(14) "The electrophotographic photosensitive member according to any one of (1) to (13) above, wherein the photosensitive layer is a single-layer type photosensitive layer".
(15) “An electrophotographic method in which at least charging, image exposure, development, and transfer are repeatedly performed on an electrophotographic photosensitive member, wherein the electrophotographic photosensitive member is any one of items (1) to (14). An electrophotographic method characterized by being an electrophotographic photosensitive member according to any one of the above.
(16) “At least charging, image exposure, development, and transfer are repeatedly performed on the electrophotographic photosensitive member, and at the time of image exposure, an electrostatic latent image is written on the photosensitive member by an LD or LED. An electrophotographic method according to claim 1, wherein the electrophotographic photosensitive member is the electrophotographic photosensitive member according to any one of the items (1) to (14).
(17) “An electrophotographic apparatus comprising at least a charging means, an image exposing means, a developing means, a transferring means, and an electrophotographic photosensitive member, wherein the electrophotographic photosensitive member is the items (1) to (14). An electrophotographic photosensitive member according to any one of the above items).
(18) “An electrophotographic apparatus comprising at least a charging unit, an image exposing unit, a developing unit, a transferring unit, and an electrophotographic photosensitive member, wherein an LD or LED is used as the image exposing unit. A digital electrophotographic apparatus in which an electrostatic latent image is written, wherein the electrophotographic photosensitive member is the electrophotographic photosensitive member according to any one of (1) to (14). An electrophotographic apparatus characterized by being. ",
(19) “A process cartridge for an electrophotographic apparatus comprising at least an electrophotographic photosensitive member, wherein the electrophotographic photosensitive member is any one of the items (1) to (14)”. A process cartridge for an electrophotographic apparatus, characterized by being a photoreceptor. "

According to the present invention, by containing the pyromellitic acid diimide-isoindole dimer derivative represented by the general formula (1), the environmental resistance to repeated use and oxidizing gas is greatly reduced without causing a decrease in sensitivity. Therefore, it has become possible to obtain a photoreceptor having high durability and high resolution image quality over a long period of time.
According to the present invention, it is possible to achieve both high durability and high image quality of an electrophotographic photosensitive member, a high-quality image can be stably obtained over a long period of time, and furthermore, an electrophotographic photosensitive member that can handle bipolar charging, and An electrophotographic method, an electrophotographic apparatus, and a process cartridge for an electrophotographic apparatus using the same are provided.

1 is a cross-sectional view illustrating an electrophotographic photosensitive member of the present invention. 1 is a cross-sectional view illustrating an electrophotographic photosensitive member of the present invention. 1 is a cross-sectional view illustrating an electrophotographic photosensitive member of the present invention. 1 is a cross-sectional view illustrating an electrophotographic photosensitive member of the present invention. 1 is a cross-sectional view illustrating an electrophotographic photosensitive member of the present invention. 1 is a cross-sectional view illustrating an electrophotographic photosensitive member of the present invention. It is the schematic for demonstrating the electrophotographic process and electrophotographic apparatus of this invention. 3 is another example of an electrophotographic process according to the present invention. FIG. 3 is a schematic view for explaining an electrophotographic process cartridge according to the present invention. It is a figure showing the powder XD spectrum of oxotitanium phthalocyanine. It is a chart which shows the IR absorption spectrum of the pyromellitic acid diimide-isoindole dimer derivative (exemplary compound No. 12) in this invention.

As a result of investigations, the present inventors have made the photosensitive layer contain at least one pyromellitic diimide-isoindole dimer derivative represented by the following general formula (1), thereby causing blurring of the oxidizing gas or the like. It has been found that a photoreceptor capable of solving problems such as image blur (image flow) due to the generated substance and capable of dealing with bipolar charging can be obtained.

［式中、Ｒ１、Ｒ２、Ｒ３およびＲ４は水素原子、置換もしくは無置換のアルキル基、置換もしくは無置換の芳香族炭化水素基、ハロゲン原子、ニトロ基を表わし、それぞれ同一でも異なっていてもよい。また、ｋは１〜４の整数を、ｌは１〜５の整数を表わす。］

[Wherein R1, R2, R3 and R4 represent a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aromatic hydrocarbon group, a halogen atom or a nitro group, which may be the same or different. . K represents an integer of 1 to 4, and l represents an integer of 1 to 5. ]

The reason why the pyromellitic acid diimide-isoindole dimer derivative in the present invention is effective for maintaining the image quality by repeated use is not clear at present, but the amino group contained in the chemical structure is a strongly basic group. Therefore, an electrical neutralizing effect on the oxidizing gas which is considered to be a causative substance of image blur is estimated.
In addition, the pyromellitic acid diimide-isoindole dimer derivative in the present invention has higher sensitivity and repeat stability when used in combination with other charge transport materials.

In addition, since the pyromellitic acid diimide-isoindole dimer derivative in the present invention is an ambipolar transporting substance, the photoconductor using it is an electron that can handle bipolar charging regardless of the type of layer structure and mixing of the transporting substance. A photographic photoreceptor can also be obtained.
Therefore, by satisfying the following constituent requirements, it is possible to achieve both high durability and high image quality, and an electrophotographic photosensitive member capable of bipolar charging that can stably obtain high-quality images even after repeated use. In addition, an electrophotographic method, an electrophotographic apparatus, and an electrophotographic process cartridge capable of stably obtaining a high-quality image even in repeated use have been provided.

Hereinafter, the electrophotographic photosensitive member of the present invention, the electrophotographic method using the same, the electrophotographic apparatus, and the electrophotographic process cartridge will be described in detail.
First, the details of the pyromellitic diimide-isoindole dimer derivative represented by the following general formula (1) to be contained in the photosensitive layer in the present invention will be described.

［式中、Ｒ１、Ｒ２、Ｒ３およびＲ４は水素原子、置換もしくは無置換のアルキル基、置換もしくは無置換の芳香族炭化水素基、ハロゲン原子、ニトロ基を表わし、それぞれ同一でも異なっていてもよい。また、ｋ及びｌは１〜４の整数を、ｍ及びｎは１〜５の整数を表わす。］

[Wherein R1, R2, R3 and R4 represent a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aromatic hydrocarbon group, a halogen atom or a nitro group, which may be the same or different. . K and l represent an integer of 1 to 4, and m and n represent an integer of 1 to 5. ]

The method for producing the pyromellitic acid diimide-isoindole dimer derivative represented by the general formula (1) can be obtained by applying the production method described in Patent Document 1.
Specifically, regarding a method for producing a symmetrical pyromellitic diimide-isoindole dimer derivative, 2 equivalents of N-amino-2,7-diphenylisoindole derivative and pyromellitic dianhydride derivative are reacted. Can be obtained.
Moreover, about the manufacturing method of asymmetrical pyromellitic diimide-isoindole dimer derivative, it is 1st step; 1 equivalent of N-amino-2,7-diphenylisoindole derivative and pyromellitic dianhydride derivative By reacting in the second step; by removing only one of them substituted with N-amino-2,7-diphenylisoindole derivative and reacting with another N-amino-2,7-diphenylisoindole derivative The pyromellitic acid diimide-isoindole dimer derivative represented by the general formula (1) can be produced.

  The solvent is not particularly limited, and examples thereof include benzene, toluene, xylene, chloronaphthalene, acetic acid, pyridine, methylpyridine, N, N-dimethylformamide, N, N-dimethylacetamide, carbon tetrachloride and the like. The reaction temperature is preferably 100 ° C. or higher.

Specific examples of the alkyl group in the description of the general formula (1) include a methyl group, an ethyl group, a propyl group, a butyl group, a hexyl group, and an undecanyl group.
In addition, aromatic hydrocarbon groups include aromatic ring groups such as benzene, biphenyl, naphthalene, anthracene, fluorene, and pyrene, and aromatic heterocyclic groups such as pyridine, quinoline, thiophene, furan, oxazole, oxadiazole, and carbazole. A halogen atom includes a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
Examples of these substituents include those exemplified in the specific examples of the alkyl group, alkoxy groups such as a methoxy group, an ethoxy group, a propoxy group, and a butoxy group, or the halogen atom, dialkylamino group, diphenylamino group, and the like. Examples thereof include a nitro group, the aromatic hydrocarbon group, and a heterocyclic group such as pyrrolidine, piperidine and piperazine.

  Preferred examples of general formula (1) are given below. However, the present invention is not limited to these compounds.

Next, the layer structure of the electrophotographic photosensitive member will be described.
FIG. 1 is a sectional view showing an electrophotographic photosensitive member of the present invention, and a photosensitive layer (33) mainly composed of a charge generating material and a charge transporting material is provided on a conductive support (31). .

  In FIG. 2, a charge generation layer (35) mainly composed of a charge generation material and a charge transport layer (37) mainly composed of a charge transport material are laminated on a conductive support (31). It has a configuration.

In FIG. 3, a photosensitive layer (33) mainly composed of a charge generation material and a charge transport material is provided on a conductive support (31), and a protective layer (39) is further provided on the surface of the photosensitive layer. . In this case, the pyromellitic acid diimide-isoindole dimer derivative of the present invention may be contained in the protective layer (39).

FIG. 4 shows a structure in which a charge generation layer (35) mainly composed of a charge generation material and a charge transport layer (37) mainly composed of a charge transport material are laminated on a conductive support (31). Further, a protective layer (39) is provided on the charge transport layer. In this case, the pyromellitic acid diimide-isoindole dimer derivative of the present invention may be contained in the protective layer (39).

  FIG. 5 shows a structure in which a charge transport layer (37) mainly composed of a charge transport material and a charge generation layer (35) mainly composed of a charge generation material are laminated on a conductive support (31). I'm taking it.

In FIG. 6, a charge transport layer (37) mainly composed of a charge transport material and a charge generation layer (35) mainly composed of a charge generation material are laminated on a conductive support (31). The protective layer (39) is further provided on the charge generation layer. In this case, the pyromellitic acid diimide-isoindole dimer derivative of the present invention may be contained in the protective layer (39).

As the conductive support (31), a material having a volume resistance of 10 ¹⁰ Ω · cm or less, for example, a metal such as aluminum, nickel, chromium, nichrome, copper, gold, silver, platinum, tin oxide, oxidation Metal oxide such as indium by vapor deposition or sputtering, film or cylindrical plastic, paper coated, or aluminum, aluminum alloy, nickel, stainless steel plates, etc. and methods such as extrusion and drawing After forming the tube, it is possible to use a tube subjected to surface treatment such as cutting, superfinishing or polishing. Further, an endless nickel belt and an endless stainless steel belt disclosed in Japanese Patent Application Laid-Open No. 52-36016 can be used as the conductive support (31).

In addition, the conductive support dispersed in a suitable binder resin and coated on the support can also be used as the conductive support (31) of the present invention.
Examples of the conductive powder include carbon black, acetylene black, metal powder such as aluminum, nickel, iron, nichrome, copper, zinc and silver, or metal oxide powder such as conductive tin oxide and ITO. It is done.
The binder resin used at the same time is polystyrene, styrene-acrylonitrile copolymer, styrene-butadiene copolymer, styrene-maleic anhydride copolymer, polyester, polyvinyl chloride, vinyl chloride-vinyl acetate copolymer. , Polyvinyl acetate, polyvinylidene chloride, polyarylate resin, phenoxy resin, polycarbonate, cellulose acetate resin, ethyl cellulose resin, polyvinyl butyral, polyvinyl formal, polyvinyl toluene, poly-N-vinylcarbazole, acrylic resin, silicone resin, epoxy resin, Examples thereof include thermoplastic, thermosetting resins, and photocurable resins such as melamine resin, urethane resin, phenol resin, and alkyd resin. Such a conductive layer can be provided by dispersing and coating these conductive powder and binder resin in a suitable solvent such as tetrahydrofuran, dichloromethane, methyl ethyl ketone, and toluene.
Furthermore, it is electrically conductive by a heat-shrinkable tube in which the conductive powder is contained in a material such as polyvinyl chloride, polypropylene, polyester, polystyrene, polyvinylidene chloride, polyethylene, chlorinated rubber, Teflon (registered trademark) on a suitable cylindrical substrate. Those provided with a conductive layer can also be used favorably as the conductive support (31) of the present invention.

  Next, the photosensitive layer will be described. The photosensitive layer may be a single layer or a laminate. For convenience of explanation, the photosensitive layer is first described from the case where it is composed of a charge generation layer (35) and a charge transport layer (37).

  The charge generation layer (35) is a layer mainly composed of a charge generation material. A known charge generation material can be used for the charge generation layer (35), and representative examples thereof include CI Pigment Blue 25 (Color Index CI 21180), CI Pigment Red 41 (CI 21200), and CI Acid Red 52. (CI 45100), CI Basic Red 3 (CI 45210), azo pigments having a carbazole skeleton (described in JP-A-53-95033), azo pigments having a distyrylbenzene skeleton (JP-A-53-133445) ), An azo pigment having a triphenylamine skeleton (described in JP-A-53-132347), an azo pigment having a dibenzothiophene skeleton (described in JP-A-54-21728), an azo pigment having an oxadiazole skeleton Pigment (Japanese Patent Laid-Open No. 54-12742) Description), an azo pigment having a fluorenone skeleton (described in JP-A-54-22834), an azo pigment having a bis-stilbene skeleton (described in JP-A-54-17733), and a distyryloxadiazole skeleton Azo pigments such as azo pigments (described in JP-A No. 54-2129), azo pigments having a distyrylcarbazole skeleton (described in JP-A No. 54-14967), and azo pigments having a benzanthrone skeleton. For example, CI Pigment Blue 16 (CI 74100), Y-type oxotitanium phthalocyanine (Japanese Unexamined Patent Publication No. 64-17066), A (β) -type oxotitanium phthalocyanine, B (α) -type oxotitanium phthalocyanine, I-type oxotitanium phthalocyanine (Described in JP-A-11-21466), type II chlorogallium phthalocyanine (Iijima et al., The 67th Annual Meeting of the Chemical Society of Japan, 1B4, 04 (1994)), type V hydroxygallium phthalocyanine (Damon et al., The Chemical Society of Japan) 67th Spring Annual Meeting, 1B4, 05 (1994)), phthalocyanine pigments such as X-type metal-free phthalocyanine (U.S. Pat. No. 3,816,118), C-Ibat Brown 5 (CI 73410), C-Ibat Dye (CI) 7330) etc. And perylene pigments such as Argo Scarlet B (manufactured by Bayer) and Insence Scarlet R (manufactured by Bayer). In addition, these materials may be used alone or in combination of two or more.

  In the charge generation layer (35), the charge generation material is dispersed in a suitable solvent together with a binder resin if necessary using a ball mill, attritor, sand mill, ultrasonic wave, etc., and this is applied onto the conductive support. And formed by drying.

As the binder resin used for the charge generation layer (35) as necessary, polyamide, polyurethane, epoxy resin, polyketone, polycarbonate, silicone resin, acrylic resin, polyvinyl butyral, polyvinyl formal, polyvinyl ketone, polystyrene, polysulfone, poly -N-vinylcarbazole, polyacrylamide, polyvinyl benzal, polyester, phenoxy resin, vinyl chloride-vinyl acetate copolymer, polyvinyl acetate, polyphenylene oxide, polyamide, polyvinyl pyridine, cellulosic resin, casein, polyvinyl alcohol, polyvinyl pyrrolidone Etc.
The amount of the binder resin is suitably 0 to 500 parts by weight, preferably 10 to 300 parts by weight with respect to 100 parts by weight of the charge generating material. The binder resin may be added before or after dispersion.

  Examples of the solvent used here include isopropanol, acetone, methyl ethyl ketone, cyclohexanone, tetrahydrofuran, dioxane, ethyl cellosolve, ethyl acetate, methyl acetate, dichloromethane, dichloroethane, monochlorobenzene, cyclohexane, toluene, xylene, and ligroin. In particular, ketone solvents, ester solvents, and ether solvents are preferably used. These may be used alone or in combination of two or more.

  The charge generation layer (35) is mainly composed of a charge generation material, a solvent, and a binder resin, and includes any additive such as a sensitizer, a dispersant, a surfactant, and silicone oil. It may be.

As a coating method for the coating solution, a dip coating method, spray coating, beat coating, nozzle coating, spinner coating, ring coating, or the like can be used.
The film thickness of the charge generation layer (35) is suitably about 0.01 to 5 μm, preferably 0.1 to 2 μm.

  The charge transport layer (37) is a layer mainly composed of a charge transport material. The charge transport material is divided into a hole transport material, an electron transport material, and a polymer charge transport material, which will be described below.

  Examples of hole transport materials include poly-N-carbazole and derivatives thereof, poly-γ-carbazolylethyl glutamate and derivatives thereof, pyrene-formaldehyde condensates and derivatives thereof, polyvinylpyrene, polyvinylphenanthrene, oxazole derivatives, imidazole There are derivatives, triphenylamine derivatives, and compounds represented by the following general formulas (111) to (136).

（式中、Ｒ２６はメチル基、エチル基、２−ヒドロキシエチル基または２−クロルエチル基を表わし、Ｒ２９はメチル基、エチル基、ベンジル基またはフェニル基を表わし、Ｒ２８は水素原子、塩素原子、臭素原子、炭素数１〜４のアルキル基、炭素数１〜４のアルコキシ基、ジアルキルアミノ基またはニトロ基を表わす。）

(Wherein R26 represents a methyl group, an ethyl group, a 2-hydroxyethyl group or a 2-chloroethyl group, R29 represents a methyl group, an ethyl group, a benzyl group or a phenyl group, R28 represents a hydrogen atom, a chlorine atom, a bromine group) Represents an atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a dialkylamino group, or a nitro group.)

  Examples of the compound represented by the general formula (111) include 9-ethylcarbazole-3-carbaldehyde 1-methyl-1-phenylhydrazone, 9-ethylcarbazole-3-carbaldehyde 1-benzyl-1-phenylhydrazone, 9-ethylcarbazole-3-carbaldehyde 1, 1-diphenylhydrazone, etc.

（式中、Ａｒ５はナフタレン環、アントラセン環、ピレン環及びそれらの置換体あるいはピリジン環、フラン環、チオフェン環を表わし、Ｒ３０はアルキル基、フェニル基またはベンジル基を表わす。）

(In the formula, Ar5 represents a naphthalene ring, an anthracene ring, a pyrene ring or a substituted product thereof, or a pyridine ring, a furan ring, or a thiophene ring, and R30 represents an alkyl group, a phenyl group, or a benzyl group.)

  Examples of the compound represented by the general formula (112) include 4-diethylaminostyryl-β-carbaldehyde 1-methyl-1-phenylhydrazone, 4-methoxynaphthalene-1-carbaldehyde 1-benzyl-1-phenylhydrazone, and the like. There is.

（式中、Ｒ３１はアルキル基、ベンジル基、フェニル基またはナフチル基を表わし、Ｒ３２は水素原子、炭素数１〜３のアルキル基、炭素数１〜３のアルコキシ基、ジアルキルアミノ基、ジアラルキルアミノ基またはジアリールアミノ基を表わし、ｎは１〜４の整数を表わし、ｎが２以上のときはＲ３２は同じでも異なっていてもよい。Ｒ３３は水素原子またはメトキシ基を表わす。）

(In the formula, R31 represents an alkyl group, a benzyl group, a phenyl group or a naphthyl group, and R32 represents a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, a dialkylamino group, a diaralkylamino group. Represents a group or a diarylamino group, n represents an integer of 1 to 4, and when n is 2 or more, R32 may be the same or different, and R33 represents a hydrogen atom or a methoxy group.)

  Examples of the compound represented by the general formula (113) include 4-methoxybenzaldehyde 1-methyl-1-phenylhydrazone, 2,4-dimethoxybenzaldehyde 1-benzyl-1-phenylhydrazone, 4-diethylaminobenzaldehyde 1,1- Examples include diphenylhydrazone, 4-methoxybenzaldehyde 1- (4-methoxy) phenylhydrazone, 4-diphenylaminobenzaldehyde 1-benzyl-1-phenylhydrazone, 4-dibenzylaminobenzaldehyde 1, 1-diphenylhydrazone.

（式中、Ｒ３４は炭素数１〜１１のアルキル基、置換もしくは無置換のフェニル基または複素環基を表わし、Ｒ３５、Ｒ３６はそれぞれ同一でも異なっていてもよく、水素原子、炭素数１〜４のアルキル基、ヒドロキシアルキル基、クロルアルキル基または置換もしくは無置換のアラルキル基を表わし、また、Ｒ３５とＲ３６は互いに結合し窒素を含む複素環を形成していてもよい。Ｒ３７は同一でも異なっていてもよく、水素原子、炭素数１〜４のアルキル基、アルコキシ基またはハロゲン原子を表わす。）

(In the formula, R34 represents an alkyl group having 1 to 11 carbon atoms, a substituted or unsubstituted phenyl group or a heterocyclic group, and R35 and R36 may be the same as or different from each other. And an alkyl group, a hydroxyalkyl group, a chloroalkyl group, or a substituted or unsubstituted aralkyl group, and R35 and R36 may be bonded to each other to form a nitrogen-containing heterocyclic ring. And represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group or a halogen atom.)

  Examples of the compound represented by the general formula (114) include 1,1-bis (4-dibenzylaminophenyl) propane, tris (4-diethylaminophenyl) methane, and 1,1-bis (4-dibenzylaminophenyl). ) Propane, 2,2′-dimethyl-4,4′-bis (diethylamino) -triphenylmethane, and the like.

（式中、Ｒ３８は水素原子またはハロゲン原子を表わし、Ａｒ６は置換もしくは無置換のフェニル基、ナフチル基、アントリル基またはカルバゾリル基を表わす。）

(In the formula, R38 represents a hydrogen atom or a halogen atom, and Ar6 represents a substituted or unsubstituted phenyl group, naphthyl group, anthryl group or carbazolyl group.)

  Examples of the compound represented by the general formula (115) include 9- (4-diethylaminostyryl) anthracene and 9-bromo-10- (4-diethylaminostyryl) anthracene.

（式中、Ｒ３９は水素原子、ハロゲン原子、シアノ基、炭素数１〜４のアルコキシ基または炭素数１〜４のアルキル基を表わし、Ａｒ７は下記一般式（１１７）、一般式（１１８）の基を表わす。）

(In the formula, R39 represents a hydrogen atom, a halogen atom, a cyano group, an alkoxy group having 1 to 4 carbon atoms or an alkyl group having 1 to 4 carbon atoms, and Ar7 represents one of the following general formulas (117) and (118). Represents a group.)

（式中、Ｒ４０は炭素数１〜４のアルキル基を表わす。）

(In the formula, R40 represents an alkyl group having 1 to 4 carbon atoms.)

（式中、Ｒ４１は水素原子、ハロゲン原子、炭素数１〜４のアルキル基、炭素数１〜４のアルコキシ基またはジアルキルアミノ基を表わし、ｎは１または２であって、ｎが２のとき、Ｒ４１は同一でも異なっていてもよく、Ｒ４２、Ｒ４３は水素原子、炭素数１〜４の置換もしくは無置換のアルキル基または置換もしくは無置換のベンジル基を表わす。）

(In the formula, R41 represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a dialkylamino group, and n is 1 or 2, where n is 2. R41 may be the same or different, and R42 and R43 each represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted benzyl group.)

  Examples of the compound represented by the general formula (116) include 9- (4-dimethylaminobenzylidene) fluorene and 3- (9-fluorenylidene) -9-ethylcarbazole.

（式中、Ｒ４４はカルバゾリル基、ピリジル基、チエニル基、インドリル基、フリル基あるいはそれぞれ置換もしくは非置換のフェニル基、スチリル基、ナフチル基、またはアントリル基であって、これらの置換基がジアルキルアミノ基、アルキル基、アルコキシ基、カルボキシ基またはそのエステル、ハロゲン原子、シアノ基、アラルキルアミノ基、Ｎ−アルキル−Ｎ−アラルキルアミノ基、アミノ基、ニトロ基及びアセチルアミノ基からなる群から選ばれた基を表わす。）

Wherein R44 is a carbazolyl group, a pyridyl group, a thienyl group, an indolyl group, a furyl group, or a substituted or unsubstituted phenyl group, a styryl group, a naphthyl group, or an anthryl group, and these substituents are dialkylamino Group, alkyl group, alkoxy group, carboxy group or ester thereof, halogen atom, cyano group, aralkylamino group, N-alkyl-N-aralkylamino group, amino group, nitro group, and acetylamino group Represents a group.)

  Examples of the compound represented by the general formula (119) include 1,2-bis (4-diethylaminostyryl) benzene and 1,2-bis (2,4-dimethoxystyryl) benzene.

（式中、Ｒ４１は低級アルキル基、置換もしくは無置換のフェニル基、またはベンジル基を表わし、Ｒ４２、Ｒ４３は水素原子、低級アルキル基、低級アルコキシ基、ハロゲン原子、ニトロ基、アミノ基あるいは低級アルキル基またはベンジル基で置換されたアミノ基を表わし、ｎは１または２の整数を表わす。）

(In the formula, R41 represents a lower alkyl group, a substituted or unsubstituted phenyl group, or a benzyl group, and R42 and R43 represent a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom, a nitro group, an amino group, or a lower alkyl group. Represents an amino group substituted with a group or a benzyl group, and n represents an integer of 1 or 2.)

  Examples of the compound represented by the general formula (120) include 3-styryl-9-ethylcarbazole and 3- (4-methoxystyryl) -9-ethylcarbazole.

（式中、Ｒ４４は水素原子、アルキル基、アルコキシ基またはハロゲン原子を表わし、Ｒ４５およびＲ４６は置換もしくは無置換のアリール基を表わし、Ｒ４７は水素原子、低級アルキル基または置換もしくは無置換のフェニル基を表わし、また、Ａｒ８は置換もしくは無置換のフェニル基またはナフチル基を表わす。）

(Wherein R44 represents a hydrogen atom, an alkyl group, an alkoxy group or a halogen atom, R45 and R46 represent a substituted or unsubstituted aryl group, and R47 represents a hydrogen atom, a lower alkyl group or a substituted or unsubstituted phenyl group. Ar8 represents a substituted or unsubstituted phenyl group or naphthyl group.)

  Examples of the compound represented by the general formula (121) include 4-diphenylaminostilbene, 4-dibenzylaminostilbene, 4-ditolylaminostilbene, 1- (4-diphenylaminostyryl) naphthalene, 1- (4- And diphenylaminostyryl) naphthalene.

（式中、ｎは０または１の整数、Ｒ４８は水素原子、アルキル基または置換もしくは無置換のフェニル基を表わし、Ａｒ９は置換もしくは未置換のアリール基を表わし、Ｒ４９は置換アルキル基を含むアルキル基、あるいは置換もしくは無置換のアリール基を表わし、Ａ２は下記一般式（３）、一般式（４）の基、９−アントリル基または置換もしくは無置換のカルバゾリル基を表わす。）

(In the formula, n represents an integer of 0 or 1, R48 represents a hydrogen atom, an alkyl group or a substituted or unsubstituted phenyl group, Ar9 represents a substituted or unsubstituted aryl group, and R49 represents an alkyl containing a substituted alkyl group. Represents a group, or a substituted or unsubstituted aryl group, and A2 represents a group of the following general formula (3), general formula (4), 9-anthryl group or substituted or unsubstituted carbazolyl group.

（ここでＲ６は水素原子、アルキル基、アルコキシ基、ハロゲン原子または一般式（５）のアリール置換アミノ基を表わす。）

(Here, R6 represents a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom or an aryl-substituted amino group of the general formula (5).)

（ただし、Ｒ７およびＲ８は置換もしくは無置換のアルキル基、置換もしくは無置換の芳香族炭化水素基を示し、Ｒ７およびＲ８は同じでも異なっていてもよく、環を形成してもよい）

(However, R7 and R8 represent a substituted or unsubstituted alkyl group or a substituted or unsubstituted aromatic hydrocarbon group, and R7 and R8 may be the same or different and may form a ring)

  Examples of the compound represented by the general formula (122) include 4'-diphenylamino-α-phenylstilbene and 4'-bis (4-methylphenyl) amino-α-phenylstilbene.

（式中、Ｒ５０、Ｒ５１およびＲ５２は水素原子、低級アルキル基、低級アルコキシ基、ハロゲン原子またはジアルキルアミノ基を表わし、ｎは０または１を表わす。）

(Wherein R50, R51 and R52 represent a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a dialkylamino group, and n represents 0 or 1)

  Examples of the compound represented by the general formula (123) include 1-phenyl-3- (4-diethylaminostyryl) -5- (4-diethylaminophenyl) pyrazoline.

（式中、Ｒ５３およびＲ５４は置換アルキル基を含むアルキル基、または置換もしくは未置換のアリール基を表わし、Ａは置換アミノ基、置換もしくは未置換のアリール基またはアリル基を表わす。）

(Wherein R53 and R54 represent an alkyl group containing a substituted alkyl group, or a substituted or unsubstituted aryl group, and A represents a substituted amino group, a substituted or unsubstituted aryl group, or an allyl group.)

  Examples of the compound represented by the general formula (124) include 2,5-bis (4-diethylaminophenyl) -1,3,4-oxadiazole, 2-N, N-diphenylamino-5- (4- And diethyl (aminophenyl) -1,3,4-oxadiazole and 2- (4-dimethylaminophenyl) -5- (4-diethylaminophenyl) -1,3,4-oxadiazole.

（式中、Ｘは水素原子、低級アルキル基またはハロゲン原子を表わし、Ｒ５５は置換アルキル基を含むアルキル基、または置換もしくは無置換のアリール基を表わし、Ａは置換アミノ基または置換もしくは無置換のアリール基を表わす。）

Wherein X represents a hydrogen atom, a lower alkyl group or a halogen atom, R55 represents an alkyl group containing a substituted alkyl group, or a substituted or unsubstituted aryl group, and A represents a substituted amino group or a substituted or unsubstituted group. Represents an aryl group.)

  Examples of the compound represented by the general formula (125) include 2-N, N-diphenylamino-5- (N-ethylcarbazol-3-yl) -1,3,4-oxadiazole, 2- (4 -Diethylaminophenyl) -5- (N-ethylcarbazol-3-yl) -1,3,4-oxadiazole.

（式中、Ｒ５６は低級アルキル基、低級アルコキシ基またはハロゲン原子を表わし、Ｒ５７、Ｒ５８は同じでも異なっていてもよく、水素原子、低級アルキル基、低級アルコキシ基またはハロゲン原子を表わし、ｌ、ｍ、ｎは０〜４の整数を表わす。）

(In the formula, R56 represents a lower alkyl group, a lower alkoxy group or a halogen atom, R57 and R58 may be the same or different, and each represents a hydrogen atom, a lower alkyl group, a lower alkoxy group or a halogen atom; N represents an integer of 0 to 4.)

  Examples of the benzidine compound represented by the general formula (126) include N, N′-diphenyl-N, N′-bis (3-methylphenyl)-[1,1′-biphenyl] -4,4′-diamine. 3,3′-dimethyl-N, N, N ′, N′-tetrakis (4-methylphenyl)-[1,1′-biphenyl] -4,4′-diamine.

（式中、Ｒ５９、Ｒ６１およびＲ６２は水素原子、アミノ基、アルコキシ基、チオアルコキシ基、アリールオキシ基、メチレンジオキシ基、置換もしくは無置換のアルキル基、ハロゲン原子または置換もしくは無置換のアリール基を、Ｒ６０は水素原子、アルコキシ基、置換もしくは無置換のアルキル基またはハロゲン原子を表わす。ただし、Ｒ５９、Ｒ６０、Ｒ６１およびＲ６２はすべて水素原子である場合は除く。また、ｋ、ｌ、ｍおよびｎは１、２、３または４の整数であり、それぞれが２、３または４の整数のときは、前記Ｒ５９、Ｒ６０、Ｒ６１およびＲ６２は同じでも異なっていてもよい。）

Wherein R59, R61 and R62 are a hydrogen atom, amino group, alkoxy group, thioalkoxy group, aryloxy group, methylenedioxy group, substituted or unsubstituted alkyl group, halogen atom or substituted or unsubstituted aryl group R60 represents a hydrogen atom, an alkoxy group, a substituted or unsubstituted alkyl group or a halogen atom, except that R59, R60, R61 and R62 are all hydrogen atoms, and k, l, m and n is an integer of 1, 2, 3 or 4, and when each is an integer of 2, 3 or 4, the R59, R60, R61 and R62 may be the same or different.)

  Examples of the biphenylamine compound represented by the general formula (127) include 4′-methoxy-N, N-diphenyl- [1,1′-biphenyl] -4-amine, 4′-methyl-N, N-bis. (4-methylphenyl)-[1,1′-biphenyl] -4-amine, 4′-methoxy-N, N-bis (4-methylphenyl)-[1,1′-biphenyl] -4-amine, N, N-bis (3,4-dimethylphenyl)-[1,1′-biphenyl] -4-amine and the like.

（式中、Ａｒ１０は置換基を有してもよい炭素数１８個以下の縮合多環式炭化水素基を表わし、また、Ｒ６３およびＲ６４は水素原子、ハロゲン原子、置換もしくは無置換のアルキル基、アルコキシ基、置換もしくは無置換のフェニル基を表わし、それぞれ同じでも異なっていてもよい。ｎは１もしくは２の整数を表わす。）

(In the formula, Ar10 represents an optionally substituted condensed polycyclic hydrocarbon group having 18 or less carbon atoms, and R63 and R64 each represents a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, Represents an alkoxy group or a substituted or unsubstituted phenyl group, which may be the same or different, and n represents an integer of 1 or 2.)

  Examples of the triarylamine compound represented by the general formula (128) include N, N-diphenyl-pyrene-1-amine, N, N-di-p-tolyl-pyren-1-amine, and N, N-di. -P-tolyl-1-naphthylamine, N, N-di (p-tolyl) -1-phenanthrylamine, 9,9-dimethyl-2- (di-p-tolylamino) fluorene, N, N, N ' , N′-tetrakis (4-methylphenyl) -phenanthrene-9,10-diamine, N, N, N ′, N′-tetrakis (3-methylphenyl) -m-phenylenediamine, and the like.

（式中、Ａｒ１１は置換もしくは無置換の芳香族炭化水素基を表わし、Ａは一般式（１３０）の基を表わす。）

(In the formula, Ar11 represents a substituted or unsubstituted aromatic hydrocarbon group, and A represents a group of the general formula (130).)

（ただし、Ａｒ１２は置換もしくは無置換の芳香族炭化水素基を表わし、Ｒ６５およびＲ６６は置換もしくは無置換のアルキル基、または置換もしくは無置換のアリール基である。）

(However, Ar12 represents a substituted or unsubstituted aromatic hydrocarbon group, and R65 and R66 are a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.)

  Examples of the diolefin aromatic compound represented by the general formula (129) include 1,4-bis (4-diphenylaminostyryl) benzene and 1,4-bis [4-di (p-tolyl) aminostyryl] benzene. and so on.

（式中、Ａｒ１２は置換もしくは無置換の芳香族炭化水素基を、Ｒ６７は水素原子、置換もしくは無置換のアルキル基、または置換もしくは無置換のアリール基を表わす。ｎは０または１、ｍは１または２であって、ｎ＝０、ｍ＝１の場合、Ａｒ１２とＲ６７は共同で環を形成してもよい。）

(In the formula, Ar12 represents a substituted or unsubstituted aromatic hydrocarbon group, R67 represents a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. N is 0 or 1, and m is When 1 or 2 and n = 0 and m = 1, Ar12 and R67 may form a ring together.)

  Examples of the styrylpyrene compound represented by the general formula (131) include 1- (4-diphenylaminostyryl) pyrene and 1- (N, N-di-p-tolyl-4-aminostyryl) pyrene.

  Examples of the electron transport material include chloroanil, bromoanil, tetracyanoethylene, tetracyanoquinodimethane, 2,4,7-trinitro-9-fluorenone, 2,4,5,7-tetranitro-9-fluorenone, 2,4,5,7-tetranitroxanthone, 2,4,8-trinitrothioxanthone, 2,6,8-trinitro-indeno4H-indeno [1,2-b] thiophen-4-one, 1,3 , 7-trinitrodibenzothiophene-5,5-dioxide and the like, and the electron transport materials listed in the following general formulas (132), (133), (134) and (135) are preferably used. be able to. These charge transport materials may be used alone or in combination of two or more.

（式中、Ｒ６８、Ｒ６９およびＲ７０は水素原子、ハロゲン原子、置換もしくは無置換のアルキル基、アルコキシ基、置換もしくは無置換のフェニル基を表わし、それぞれ同じでも異なっていてもよい。）

(In the formula, R68, R69 and R70 represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, an alkoxy group, or a substituted or unsubstituted phenyl group, which may be the same or different.)

（式中、Ｒ７１、Ｒ７２は水素原子、置換もしくは無置換のアルキル基、置換もしくは無置換のフェニル基を表わし、それぞれ同じでも異なっていてもよい。）

(In the formula, R71 and R72 each represents a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted phenyl group, which may be the same or different.)

（式中Ｒ７３、Ｒ７４およびＲ７５は水素原子、ハロゲン原子、置換もしくは無置換のアルキル基、アルコキシ基、置換もしくは無置換のフェニル基を表わし、それぞれ同じでも異なっていてもよい。）

(Wherein R73, R74 and R75 each represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, an alkoxy group or a substituted or unsubstituted phenyl group, and may be the same or different.)

（式中、Ｒ７６は置換基を有してもよいアルキル基、または置換基を有してもよいアリール基を示し、Ｒ７７は置換基を有してもよいアルキル基、置換基を有してもよいアリール基、または下記式一般式（３６）で表わされる基を示す。）

(In the formula, R76 represents an alkyl group which may have a substituent or an aryl group which may have a substituent, and R77 has an alkyl group which may have a substituent or a substituent. Or a group represented by the following formula (36):

（式中、Ｒ７８は、置換基を有してもよいアルキル基、または置換基を有してもよいアリール基を示す。）

(In the formula, R78 represents an alkyl group which may have a substituent, or an aryl group which may have a substituent.)

  As the binder resin, polystyrene, styrene-acrylonitrile copolymer, styrene-butadiene copolymer, styrene-maleic anhydride copolymer, polyester, polyvinyl chloride, vinyl chloride-vinyl acetate copolymer, polyvinyl acetate, Polyvinylidene chloride, polyarylate resin, phenoxy resin, polycarbonate, cellulose acetate resin, ethyl cellulose resin, polyvinyl butyral, polyvinyl formal, polyvinyl toluene, poly-N-vinyl carbazole, acrylic resin, silicone resin, epoxy resin, melamine resin, urethane resin And thermoplastic or thermosetting resins such as phenol resins and alkyd resins.

When the charge transport material and the naphthalimide-isoindole derivative of the present invention are mixed and contained in the charge transport layer, the total amount is 20 to 300 parts by weight, preferably 40 to 150 parts by weight with respect to 100 parts by weight of the binder resin. Part by weight is appropriate.
The thickness of the charge transport layer is preferably 25 μm or less from the viewpoint of resolution and responsiveness. Regarding the lower limit, although it differs depending on the system to be used (particularly the charging potential), it is preferably 5 μm or more.

The amount of the naphthalimide-isoindole derivative of the present invention is preferably 0.01 wt% to 150 wt% with respect to the charge transport material. If the amount is too small, the resistance to the oxidizing gas is insufficient. If the amount is too large, the residual potential increases greatly due to repeated use.
As the solvent used here, tetrahydrofuran, dioxane, toluene, dichloromethane, monochlorobenzene, dichloroethane, cyclohexanone, methyl ethyl ketone, acetone or the like is used. The charge transport materials may be used alone or in combination of two or more.

As the antioxidant that can be used in the present invention, a general antioxidant described later can be used, and (c) hydroquinone-based compounds and (f) hindered amine-based compounds are particularly effective.
However, the antioxidant used here is used for the alteration protection of the naphthalimide-isoindole derivative used in the present invention, unlike the purpose described later.
For this reason, these antioxidants are preferably contained in the coating solution in the step prior to containing the naphthalimide-isoindole derivative of the present invention. On the other hand, a sufficient effect can be exhibited at 0.1 to 200 wt%.

  For the charge transport layer, a polymer charge transport material having a function as a charge transport material and a function as a binder resin is also preferably used. The charge transport layer composed of these polymer charge transport materials is excellent in wear resistance. As the polymer charge transport material, known materials can be used, and in particular, a polycarbonate containing a triarylamine structure in the main chain and / or side chain is preferably used. Among these, polymer charge transport materials represented by the structural formulas (I) to (XIII) are preferably used. These are illustrated below and specific examples are shown.

（式中、Ｒ７９、Ｒ８０、Ｒ８１はそれぞれ独立して置換もしくは無置換のアルキル基又はハロゲン原子、Ｒ８１は水素原子又は置換もしくは無置換のアルキル基、Ｒ８２、Ｒ８３は置換もしくは無置換のアリール基、ｏ、ｐ、ｑはそれぞれ独立して０〜４の整数、ｋ、ｊは組成を表わし、０．１≦ｋ≦１、０≦ｊ≦０．９、ｎは繰り返し単位数を表わし５〜５０００の整数である。Ｘは脂肪族の２価基、環状脂肪族の２価基、または下記構造式（ＩＩ）で表わされる２価基を表わす。）

Wherein R79, R80 and R81 are each independently a substituted or unsubstituted alkyl group or halogen atom, R81 is a hydrogen atom or a substituted or unsubstituted alkyl group, R82 and R83 are substituted or unsubstituted aryl groups, o, p and q are each independently an integer of 0 to 4, k and j represent the composition, 0.1 ≦ k ≦ 1, 0 ≦ j ≦ 0.9, and n represents the number of repeating units of 5 to 5000. X represents an aliphatic divalent group, a cycloaliphatic divalent group, or a divalent group represented by the following structural formula (II).

（式中、Ｒ８４、Ｒ８５は各々独立して置換もしくは無置換のアルキル基、アリール基またはハロゲン原子を表わす。ｌ、ｍは０〜４の整数、Ｙは単結合、炭素原子数１〜１２の直鎖状、分岐状もしくは環状のアルキレン基、−Ｏ−、−Ｓ−、−ＳＯ−、−ＳＯ２−、−ＣＯ−、−ＣＯ−Ｏ−Ｚ−Ｏ−ＣＯ−（式中Ｚは脂肪族の２価基を表わす。）または、下記構造式（ＩＩＩ）を表わす。）

(Wherein R84 and R85 each independently represents a substituted or unsubstituted alkyl group, aryl group or halogen atom. L and m are integers of 0 to 4, Y is a single bond, and has 1 to 12 carbon atoms. Linear, branched or cyclic alkylene group, —O—, —S—, —SO—, —SO 2 —, —CO—, —CO—O—Z—O—CO— (wherein Z is aliphatic) Or the following structural formula (III) :)

（式中、ａは１〜２０の整数、ｂは１〜２０００の整数、Ｒ８６、Ｒ８７は置換または無置換のアルキル基又はアリール基を表わす。）を表わす。ここで、Ｒ８６とＲ８７は、それぞれ同一でも異なってもよい。）

(Wherein, a represents an integer of 1 to 20, b represents an integer of 1 to 2000, and R86 and R87 represent a substituted or unsubstituted alkyl group or an aryl group). Here, R86 and R87 may be the same or different. )

（式中、Ｒ８８、Ｒ８９は置換もしくは無置換のアリール基、Ａｒ１３、Ａｒ１４、Ａｒ１５は同一あるいは異なるアリレン基を表わす。Ｘ、ｋ、ｊおよびｎは、上記構造式（Ｉ）式の場合と同じである。）

(In the formula, R88 and R89 are substituted or unsubstituted aryl groups, Ar13, Ar14 and Ar15 are the same or different arylene groups. X, k, j and n are the same as in the structural formula (I) above. .)

（式中、Ｒ９０、Ｒ９１は置換もしくは無置換のアリール基、Ａｒ１６、Ａｒ１７、Ａｒ１８は同一あるいは異なるアリレン基を表わす。Ｘ、ｋ、ｊおよびｎは、上記構造式（Ｉ）式の場合と同じである。）

(In the formula, R90 and R91 are substituted or unsubstituted aryl groups, Ar16, Ar17 and Ar18 are the same or different arylene groups. X, k, j and n are the same as those in the structural formula (I) above. .)

（式中、Ｒ９２、Ｒ９３は置換もしくは無置換のアリール基、Ａｒ１９、Ａｒ２０、Ａｒ２１は同一あるいは異なるアリレン基、ｐは１〜５の整数を表わす。Ｘ、ｋ、ｊおよびｎは、上記構造式（Ｉ）式の場合と同じである。）

(Wherein R92 and R93 are substituted or unsubstituted aryl groups, Ar19, Ar20 and Ar21 are the same or different arylene groups, p represents an integer of 1 to 5. X, k, j and n are the structural formulas shown above. (Same as in formula (I).)

（式中、Ｒ９４、Ｒ９５は置換もしくは無置換のアリール基、Ａｒ２２、Ａｒ２３、Ａｒ２４は同一あるいは異なるアリレン基、Ｘ１、Ｘ２は置換もしくは無置換のエチレン基、又は置換もしくは無置換のビニレン基を表わす。Ｘ、ｋ、ｊおよびｎは、上記構造式（Ｉ）式の場合と同じである。）

Wherein R94 and R95 are substituted or unsubstituted aryl groups, Ar22, Ar23 and Ar24 are the same or different arylene groups, X1 and X2 are substituted or unsubstituted ethylene groups, or substituted or unsubstituted vinylene groups. X, k, j and n are the same as those in the above formula (I).)

（式中、Ｒ９６、Ｒ９７、Ｒ９８、Ｒ９９は置換もしくは無置換のアリール基、Ａｒ２５、Ａｒ２６、Ａｒ２７、Ａｒ２８は同一あるいは異なるアリレン基、Ｙ１、Ｙ２、Ｙ３は単結合、置換もしくは無置換のアルキレン基、置換もしくは無置換のシクロアルキレン基、置換もしくは無置換のアルキレンエーテル基、酸素原子、硫黄原子、ビニレン基を表わし同一であっても異なってもよい。Ｘ、ｋ、ｊおよびｎは、上記構造式（Ｉ）式の場合と同じである。）

(Wherein R96, R97, R98 and R99 are substituted or unsubstituted aryl groups, Ar25, Ar26, Ar27 and Ar28 are the same or different arylene groups, Y1, Y2 and Y3 are single bonds, substituted or unsubstituted alkylene groups. Represents a substituted or unsubstituted cycloalkylene group, a substituted or unsubstituted alkylene ether group, an oxygen atom, a sulfur atom, or a vinylene group, which may be the same or different, and X, k, j, and n each have the above structure; (Same as in the case of the formula (I).)

（式中、Ｒ１００、Ｒ１０１は水素原子、置換もしくは無置換のアリール基を表わし、Ｒ１００とＲ１０１は環を形成していてもよい。Ａｒ２９、Ａｒ３０、Ａｒ３１は同一あるいは異なるアリレン基を表わす。Ｘ、ｋ、ｊおよびｎは、上記構造式（Ｉ）式の場合と同じである。）

(Wherein R100 and R101 each represent a hydrogen atom or a substituted or unsubstituted aryl group, and R100 and R101 may form a ring. Ar29, Ar30 and Ar31 each represent the same or different arylene group; X, k, j, and n are the same as those in the above formula (I).)

（式中、Ｒ１０２は置換もしくは無置換のアリール基、Ａｒ３２、Ａｒ３３、Ａｒ３４、Ａｒ３５は同一あるいは異なるアリレン基を表わす。Ｘ、ｋ、ｊおよびｎは、上記構造式（Ｉ）式の場合と同じである。）

(In the formula, R102 represents a substituted or unsubstituted aryl group, Ar32, Ar33, Ar34, and Ar35 represent the same or different arylene groups. X, k, j, and n are the same as those in the above structural formula (I). .)

（式中、Ｒ１０３、Ｒ１０４、Ｒ１０５、Ｒ１０６は置換もしくは無置換のアリール基、Ａｒ３６、Ａｒ３７、Ａｒ３８、Ａｒ３９、Ａｒ４０は同一あるいは又は異なるアリレン基を表わす。Ｘ、ｋ、ｊおよびｎは、上記構造式（Ｉ）式の場合と同じである。）

(Wherein R103, R104, R105, and R106 represent a substituted or unsubstituted aryl group, Ar36, Ar37, Ar38, Ar39, and Ar40 represent the same or different arylene groups. X, k, j, and n represent the above structures. (Same as in the case of the formula (I).)

（式中、Ｒ１０７、Ｒ１０８は置換もしくは無置換のアリール基、Ａｒ４１、Ａｒ４２、Ａｒ４３は同一あるいは異なるアリレン基を表わす。Ｘ、ｋ、ｊおよびｎは、上記構造式（Ｉ）式の場合と同じである。）

(Wherein R107 and R108 are substituted or unsubstituted aryl groups, Ar41, Ar42 and Ar43 are the same or different arylene groups. X, k, j and n are the same as those in the structural formula (I) above. .)

（式中、Ａｒ４４、Ａｒ４５、Ａｒ４６、Ａｒ４７およびＡｒ４８は置換もしくは無置換の芳香環基、Ｚは芳香環基または−Ａｒ４９−Ｚａ−Ａｒ４９−を表わし、Ａｒ４９は置換もしくは無置換の芳香環基、ＺａはＯ、Ｓまたはアルキレン基、Ｒ１０９およびＲ１１０は直鎖又は分岐鎖のアルキレン基を表わす。ｍは０または１を表わす。ｋ、ｊ、ｎ及びＸは前式と同じである。）

(In the formula, Ar44, Ar45, Ar46, Ar47 and Ar48 represent a substituted or unsubstituted aromatic ring group, Z represents an aromatic ring group or -Ar49-Za-Ar49-, Ar49 represents a substituted or unsubstituted aromatic ring group, Za represents O, S or an alkylene group, R109 and R110 each represents a linear or branched alkylene group, m represents 0 or 1, and k, j, n and X are the same as in the previous formula.)

The charge transport layer (37) can be formed by dissolving or dispersing the charge transport material alone or in a binder resin and an appropriate solvent, and applying and drying the solution on the charge generation layer.
Further, if necessary, two or more kinds of plasticizers, leveling agents, antioxidants and the like can be added.
As a coating method of the coating liquid obtained as described above, conventional coating methods such as dip coating, spray coating, beat coating, nozzle coating, spinner coating, ring coating, and the like can be used.

Next, the case where the photosensitive layer has a single layer configuration (33) will be described.
A photoreceptor in which the above-described charge generating material is dispersed in a binder resin can be used. The photosensitive layer can be formed by dissolving or dispersing a charge generating substance, a charge transporting substance, and a binder resin in a suitable solvent, and applying and drying them.
Moreover, a plasticizer, a leveling agent, antioxidant, etc. can also be added as needed.

  As the binder resin, in addition to the binder resin previously mentioned in the charge transport layer (37), the binder resin mentioned in the charge generation layer (35) may be mixed and used. Of course, the polymer charge transport materials mentioned above can also be used favorably. The amount of the charge generating material with respect to 100 parts by weight of the binder resin is preferably 5 to 40 parts by weight, and the amount of the charge transporting material is preferably 0 to 190 parts by weight, and more preferably 50 to 150 parts by weight. The photosensitive layer is formed by dip coating, spray coating, bead coating, a coating solution in which a charge generating material and a binder resin are dispersed together with a charge transporting material using a solvent such as tetrahydrofuran, dioxane, dichloroethane, and cyclohexane. It can be formed by coating with a ring coat or the like. The film thickness of the photosensitive layer is suitably about 5 to 25 μm.

In the photoreceptor of the present invention, an undercoat layer can be provided between the conductive support (31) and the photosensitive layer.
In general, the undercoat layer is mainly composed of a resin. However, considering that the photosensitive layer is coated with a solvent on these resins, the resin may be a resin having high solvent resistance with respect to a general organic solvent. desirable.
Examples of such resins include water-soluble resins such as polyvinyl alcohol, casein, and sodium polyacrylate, alcohol-soluble resins such as copolymer nylon and methoxymethylated nylon, polyurethane, melamine resin, phenol resin, alkyd-melamine resin, and epoxy. Examples thereof include a curable resin that forms a three-dimensional network structure such as a resin.
Further, a metal oxide fine powder pigment exemplified by titanium oxide, silica, alumina, zirconium oxide, tin oxide, indium oxide and the like may be added to the undercoat layer in order to prevent moire and reduce residual potential.

These undercoat layers can be formed using an appropriate solvent and a coating method like the above-mentioned photosensitive layer.
Furthermore, a silane coupling agent, a titanium coupling agent, a chromium coupling agent, or the like can be used as the undercoat layer of the present invention.
In addition, in the undercoat layer of the present invention, Al ₂ O ₃ is provided by anodization, organic substances such as polyparaxylylene (parylene), SiO ₂ , SnO ₂ , TiO ₂ , ITO, CeO ₂ A material provided with an inorganic material such as a vacuum thin film can also be used favorably. In addition, known ones can be used. The thickness of the undercoat layer is suitably from 0 to 5 μm.

In the photoreceptor of the present invention, a protective layer (39) may be provided on the photosensitive layer for the purpose of protecting the photosensitive layer.
Materials used for the protective layer (39) include ABS resin, ACS resin, olefin-vinyl monomer copolymer, chlorinated polyether, aryl resin, phenol resin, polyacetal, polyamide, polyamideimide, polyacrylate, polyallylsulfone. , Polybutylene, polybutylene terephthalate, polycarbonate, polyethersulfone, polyethylene, polyethylene terephthalate, polyimide, acrylic resin, polymethylbenten, polypropylene, polyphenylene oxide, polysulfone, polystyrene, polyarylate, AS resin, butadiene-styrene copolymer, polyurethane , Resins such as polyvinyl chloride, polyvinylidene chloride, and epoxy resin. From the viewpoint of filler dispersibility, residual potential, and coating film defects, polycarbonate or polyarylate is particularly effective and useful.

A filler material is added to the protective layer of the photoreceptor for the purpose of improving the wear resistance.
As the solvent used, all solvents used in the charge transport layer (37) such as tetrahydrofuran, dioxane, toluene, dichloromethane, monochlorobenzene, dichloroethane, cyclohexanone, methyl ethyl ketone, acetone and the like can be used.
However, a solvent having a high viscosity is preferable at the time of dispersion, but a solvent having high volatility is preferable at the time of coating. When there is no solvent satisfying these conditions, it is possible to use a mixture of two or more solvents having respective physical properties, which may have a great effect on filler dispersibility and residual potential. .

Further, the pyromellitic acid diimide-isoindole dimer derivative of the present invention may be contained in the protective layer. Furthermore, the addition of the low molecular charge transport material or the polymer charge transport material mentioned in the charge transport layer (37) is effective and useful for reducing the residual potential and improving the image quality.

  As a method for forming the protective layer, conventional methods such as dip coating, spray coating, beat coating, nozzle coating, spinner coating, ring coating, etc. can be used. preferable.

In the photoreceptor of the present invention, an intermediate layer can be provided between the photosensitive layer and the protective layer.
In the intermediate layer, a binder resin is generally used as a main component.
Examples of these resins include polyamide, alcohol-soluble nylon, water-soluble polyvinyl butyral, polyvinyl butyral, and polyvinyl alcohol. As a method for forming the intermediate layer, a generally used coating method as described above is employed. In addition, about 0.05-2 micrometers is suitable for the thickness of an intermediate | middle layer.

In the present invention, in order to improve environmental resistance, in order to prevent a decrease in sensitivity and an increase in residual potential, oxidation is performed on each layer such as a charge generation layer, a charge transport layer, an undercoat layer, a protective layer, and an intermediate layer. Inhibitors, plasticizers, lubricants, UV absorbers and leveling agents can be added.
Representative materials of these compounds are described below.
Examples of the antioxidant that can be added to each layer include, but are not limited to, the following.

(A) Phenolic compounds 2,6-di-t-butyl-p-cresol, butylated hydroxyanisole, 2,6-di-t-butyl-4-ethylphenol, n-octadecyl -3- (4'-hydroxy-3 ', 5'-di-tert-butylphenol), 2,2'-methylene-bis- (4-methyl-6-tert-butylphenol), 2,2'- Methylene-bis- (4-ethyl-6-tert-butylphenol), 4,4′-thiobis- (3-methyl-6-tert-butylphenol), 4,4′-butylidenebis- (3-methyl) -6-tert-butylphenol), 1,1,3-tris- (2-methyl-4-hydroxy-5-tert-butylphenyl) butane, 1,3,5-trimethyl-2,4,6- Tris (3,5-di-tert-butyl-4-hydroxybenzyl) benzene, te Lakis- [methylene-3- (3 ′, 5′-di-t-butyl-4′-hydroxyphenyl) propionate] methane, bis [3,3′-bis (4′-hydroxy-3′-t) -Butylphenyl) butyric acid] cricol ester, tocopherols and the like.

(B) Paraphenylenediamines N-phenyl-N′-isopropyl-p-phenylenediamine, N, N′-di-sec-butyl-p-phenylenediamine, N-phenyl-N-sec-butyl-p-phenylene Diamine, N, N′-di-isopropyl-p-phenylenediamine, N, N′-dimethyl-N, N′-di-t-butyl-p-phenylenediamine and the like.

(C) Hydroquinones 2,5-di-t-octylhydroquinone, 2,6-didodecylhydroquinone, 2-dodecylhydroquinone, 2-dodecyl-5-chlorohydroquinone, 2-t-octyl-5-methylhydroquinone, 2 -(2-octadecenyl) -5-methylhydroquinone and the like.

(D) Organic sulfur compounds Dilauryl-3,3′-thiodipropionate, distearyl-3,3′-thiodipropionate, ditetradecyl-3,3′-thiodipropionate, and the like.

(E) Organic phosphorus compounds Triphenylphosphine, tri (nonylphenyl) phosphine, tri (dinonylphenyl) phosphine, tricresylphosphine, tri (2,4-dibutylphenoxy) phosphine and the like.

  Examples of the plasticizer that can be added to each layer include, but are not limited to, the following.

(A) Phosphate ester plasticizer Triphenyl phosphate, tricresyl phosphate, trioctyl phosphate, octyl diphenyl phosphate, trichloroethyl phosphate, cresyl diphenyl phosphate, tributyl phosphate, tri-2-ethylhexyl phosphate, Triphenyl phosphate etc.

(B) Phthalate ester plasticizers Dimethyl phthalate, diethyl phthalate, diisobutyl phthalate, dibutyl phthalate, diheptyl phthalate, di-2-ethylhexyl phthalate, diisooctyl phthalate, di-n-octyl phthalate, phthalate Dinonyl acid, diisononyl phthalate, diisodecyl phthalate, diundecyl phthalate, ditridecyl phthalate, dicyclohexyl phthalate, butyl benzyl phthalate, butyl lauryl phthalate, methyl oleyl phthalate, octyl decyl phthalate, dibutyl fumarate, dioctyl fumarate Such.

(C) Aromatic carboxylic acid ester plasticizers Trioctyl trimellitic acid, tri-n-octyl trimellitic acid, octyl oxybenzoate, and the like.

(D) Aliphatic dibasic ester plasticizer dibutyl adipate, di-n-hexyl adipate, di-2-ethylhexyl adipate, di-n-octyl adipate, adipic acid n-octyl-n-decyl , Diisodecyl adipate, dicapryl adipate, di-2-ethylhexyl azelate, dimethyl sebacate, diethyl sebacate, dibutyl sebacate, di-n-octyl sebacate, di-2-ethylhexyl sebacate, di-2 sebacate -Ethoxyethyl, dioctyl succinate, diisodecyl succinate, dioctyl tetrahydrophthalate, di-n-octyl tetrahydrophthalate and the like.

(E) Fatty acid ester derivatives butyl oleate, glycerin monooleate, methyl acetylricinoleate, pentaerythritol ester, dipentaerythritol hexaester, triacetin, tributyrin and the like.

(F) Oxyacid ester plasticizers Methyl acetyl ricinoleate, butyl acetyl ricinoleate, butyl phthalyl butyl glycolate, tributyl acetyl citrate and the like.

(G) Epoxy plasticizer Epoxidized soybean oil, epoxidized linseed oil, butyl epoxy stearate, decyl epoxy stearate, octyl epoxy stearate, benzyl epoxy stearate, dioctyl epoxy hexahydrophthalate, didecyl epoxy hexahydrophthalate, etc. .

(H) Dihydric alcohol ester plasticizers such as diethylene glycol dibenzoate and triethylene glycol di-2-ethylbutyrate.

(I) Chlorinated plasticizer Chlorinated paraffin, chlorinated diphenyl, chlorinated fatty acid methyl, methoxychlorinated fatty acid methyl and the like.

(J) Polyester plasticizer Polypropylene adipate, polypropylene sebacate, polyester, acetylated polyester and the like.

(K) Sulfonic acid derivatives p-toluenesulfonamide, o-toluenesulfonamide, p-toluenesulfoneethylamide, o-toluenesulfoneethylamide, toluenesulfone-N-ethylamide, p-toluenesulfone-N-cyclohexylamide and the like.

(L) Citric acid derivatives Triethyl citrate, triethyl acetylcitrate, tributyl citrate, tributyl acetylcitrate, tri-2-ethylhexyl acetylcitrate, acetylcitrate-n-octyldecyl, and the like.

(M) Others Terphenyl, partially hydrogenated terphenyl, camphor, 2-nitrodiphenyl, dinonylnaphthalene, methyl abietate and the like.

  Examples of the lubricant that can be added to each layer include, but are not limited to, the following.

(A) Hydrocarbon compounds Liquid paraffin, paraffin wax, microwax, low-polymerized polyethylene and the like.

(B) Fatty acid compounds Lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, behenic acid and the like.

(C) Fatty acid amide compounds Stearylamide, palmitylamide, oleinamide, methylenebisstearamide, ethylenebisstearamide and the like.

(D) Ester compounds Lower alcohol esters of fatty acids, polyhydric alcohol esters of fatty acids, fatty acid polyglycol esters, and the like.

(E) Alcohol compounds Cetyl alcohol, stearyl alcohol, ethylene glycol, polyethylene glycol, polyglycerol and the like.

(F) Metal soap Lead stearate, cadmium stearate, barium stearate, calcium stearate, zinc stearate, magnesium stearate and the like.

(G) Natural wax Carnauba wax, candelilla wax, beeswax, whale wax, ivotaro, montan wax and the like.

(H) Others Silicone compounds, fluorine compounds, etc.

  Examples of the ultraviolet absorber that can be added to each layer include, but are not limited to, the following.

(A) Benzophenone series 2-hydroxybenzophenone, 2,4-dihydroxybenzophenone, 2,2 ′, 4-trihydroxybenzophenone, 2,2 ′, 4,4′-tetrahydroxybenzophenone, 2,2′-dihydroxy-4- Such as methoxybenzophenone.

(B) Salsylate type Phenyl salsylate, 2,4-di-t-butylphenyl-3,5-di-t-butyl-4-hydroxybenzoate, and the like.

(C) Benzotriazole series (2′-hydroxyphenyl) benzotriazole, (2′-hydroxy5′-methylphenyl) benzotriazole, (2′-hydroxy5′-methylphenyl) benzotriazole, (2′-hydroxy3) '-Tert-butyl-5'-methylphenyl) 5-chlorobenzotriazole

(D) Cyanoacrylate-based ethyl-2-cyano-3,3-diphenyl acrylate, methyl 2-carbomethoxy-3- (paramethoxy) acrylate, and the like.

(E) Quencher (metal complex)
Nickel (2,2′thiobis (4-t-octyl) phenolate) normal butylamine, nickel dibutyldithiocarbamate, nickel dibutyldithiocarbamate, cobalt dicyclohexyldithiophosphate and the like.

(F) HALS (hindered amine)
Bis (2,2,6,6-tetramethyl-4-piperidyl) sebacate, bis (1,2,2,6,6-pentamethyl-4-piperidyl) sebacate, 1- [2- [3- (3 5-di-t-butyl-4-hydroxyphenyl) propionyloxy] ethyl] -4- [3- (3,5-di-t-butyl-4-hydroxyphenyl) propionyloxy] -2,2,6 6-tetramethylpyridine, 8-benzyl-7,7,9,9-tetramethyl-3-octyl-1,3,8-triazaspiro [4,5] undecane-2,4-dione, 4-benzoyloxy- 2,2,6,6-tetramethylpiperidine and the like.

  Next, the electrophotographic method and the electrophotographic apparatus of the present invention will be described in detail with reference to the drawings.

FIG. 7 is a schematic view for explaining the electrophotographic process and the electrophotographic apparatus of the present invention, and the following examples also belong to the category of the present invention.
In FIG. 7, the photoconductor (1) has a drum shape, but it may be a sheet or an endless belt. A charging charger (3), a pre-transfer charger (7), a transfer charger (10), a separation charger (11), and a pre-cleaning charger (13) include a corotron, a scorotron, a solid state charger, and charging. A roller or the like is used, and all known means can be used.
As the transfer means, the above charger can be generally used. However, as shown in the figure, a combination of a transfer charger and a separation charger is effective.
Further, light sources such as an image exposure unit (5) and a charge removal lamp (2) include fluorescent lamps, tungsten lamps, halogen lamps, mercury lamps, sodium lamps, light emitting diodes (LEDs), semiconductor lasers (LD), and electroluminescence (EL). ) And other luminescent materials can be used. Various types of filters such as a sharp cut filter, a band pass filter, a near infrared cut filter, a dichroic filter, an interference filter, and a color temperature conversion filter can be used to irradiate only light in a desired wavelength range.
In addition to the steps shown in FIG. 7, the light source and the like are provided with a transfer step, a static elimination step, a cleaning step, a pre-exposure step and the like using light irradiation together, so that the photosensitive member is irradiated with light.
The toner developed on the photoconductor (1) by the developing unit (6) is transferred to the transfer paper (9), but not all is transferred and remains on the photoconductor (1). Toner is also produced. Such toner is removed from the photoreceptor by the fur brush (14) and the blade (15). Cleaning may be performed only with a cleaning brush, and a known brush such as a fur brush or a mag fur brush is used as the cleaning brush.
When the electrophotographic photosensitive member is positively (negatively) charged and image exposure is performed, a positive (negative) electrostatic latent image is formed on the surface of the photosensitive member. A positive image can be obtained by developing this with negative (positive) toner (electrodetection fine particles), and a negative image can be obtained by developing with positive (negative) toner. A known method is applied to the developing unit, and a known method is also used for the charge eliminating unit.

  FIG. 8 shows another example of the electrophotographic process according to the present invention. The photosensitive member (21) has at least a photosensitive layer and is driven by driving rollers (22a) and (22b), and is charged by a charging charger (23), image exposure by a light source (24), development (not shown), transfer. Transfer using the charger (25), exposure before cleaning using the light source (26), cleaning using the brush (27), and static elimination using the light source (28) are repeated. In FIG. 8, the photoconductor (21) (of course, the support is translucent in this case) is irradiated with pre-cleaning exposure light from the support side.

The above illustrated electrophotographic process is illustrative of an embodiment of the present invention, and of course other embodiments are possible.
For example, in FIG. 8, the pre-cleaning exposure is performed from the support side, but this may be performed from the photosensitive layer side, or image exposure and neutralization light irradiation may be performed from the support side.

  On the other hand, the light irradiation process is illustrated as image exposure, pre-cleaning exposure, and static elimination exposure. In addition, a pre-transfer exposure, a pre-exposure of image exposure, and other known light irradiation processes are provided to light the photosensitive member. Irradiation can also be performed.

The image forming means as described above may be fixedly incorporated in a copying apparatus, a facsimile, or a printer, but may be incorporated in these apparatuses in the form of a process cartridge. A process cartridge is a single device (part) that contains a photosensitive member and includes a charging unit, an exposure unit, a developing unit, a transfer unit, a cleaning unit, and a charge eliminating unit.
There are many shapes and the like of the process cartridge, but a general example is shown in FIG. The photoreceptor (16) has at least a photosensitive layer on a conductive support.

[Production example]
(Production Example of Exemplified Compound No. 12)
1-amino-2,7-diphenyl-4,5-dimethylisoindole 5.25 g (16.8 mmol), pyromellitic dianhydride 1.74 g (8 mmol), N, N-dimethylformamide (dehydrated) 100 ml, And 4 ml of acetic acid were added to the flask and heated to reflux for 4 hours. After cooling, the solvent was distilled off under reduced pressure. The residue was dissolved in toluene and purified by silica gel chromatography. Further, recrystallization was performed with a methanol / toluene mixed solvent to obtain 1.21 g of a pyromellitic acid diimide derivative (yield 18.7%) as black-green plate crystals. The melting point was 250 ° C. or higher.
FIG. 11 shows the IR spectrum.

  EXAMPLES Hereinafter, although an Example is given and this invention is demonstrated, this invention is not restrict | limited by an Example. All parts are parts by weight.

An undercoat layer coating solution, a charge generation layer coating solution, and a charge transport layer coating solution having the following composition are sequentially applied onto an aluminum cylinder by dip coating and dried to obtain a 3.5 μm undercoat layer, 0. A 2 μm charge generation layer and a 23 μm charge transport layer were formed (photosensitive member No. 1).
◎ Undercoat layer coating liquid / titanium dioxide powder (Ishihara Sangyo, Tybak CR-EL): 400 parts / Melamine resin (Dainippon Ink, Super Becamine G821-60): 65 parts / Alkyd resin (Dainippon Ink) Manufactured by Beckolite M6401-50): 120 parts, 2-butanone: 400 parts, charge generation layer coating solution, fluorenone-based bisazo pigment having the following structure: 12 parts, polyvinyl butyral (manufactured by Union Carbide, XYHL): 5 parts 2-butanone: 200 parts, cyclohexanone: 400 parts

Charge transport layer coating solution / polycarbonate resin (Z Polyca, manufactured by Teijin Chemicals): 10 parts 12 pyromellitic acid diimide-isoindole dimer derivatives: 10 parts Tetrahydrofuran: 100 parts

Ricoh's imagio MF2200 remodeling machine, in which the electrophotographic photosensitive member produced as described above is mounted on an electrophotographic process cartridge, the charging method is a positive charging corona charging method, and the image exposure light source is a 655 nm semiconductor laser (LD). After setting the dark part potential to 800 (V), a repeated test corresponding to printing a total of 100,000 sheets was continuously performed. At that time, the initial portion and the bright portion potential (V) and the image after the repeated test were evaluated.
In addition, for image blur (dot resolution), ten consecutive dot images with a pixel density of 600 dpi × 600 dpi and an image density of 5% are printed out, and the dot shape is observed with a stereomicroscope. The evaluation was divided into five levels (5 is excellent and 1 is inferior).

(Dot image evaluation criteria)
5: The outline is clear and good.
4: Very slight blurring of outline is observed, but good.
3: Substantially blurred outline is observed, but substantially good.
2: Blurred outlines are observed, which may be a problem depending on the type of image.
1: The dot image cannot be identified.
The results are shown in Table 2.

In Example 1, Exemplified Compound No. No. 12 pyromellitic acid diimide-isoindole dimer derivative was prepared by way of Example Compound No. The electrophotographic photosensitive member No. 1 was changed in the same manner as in Example 1 except that the derivative was changed to the derivative No. 1. 2 was prepared and evaluated.
The results are also shown in Table 2.

In Example 1, Exemplified Compound No. No. 12 pyromellitic acid diimide-isoindole dimer derivative was exemplified as Compound No. Except for the change to the derivative of No. 3, the electrophotographic photoreceptor No. 3 was made and evaluated.
The results are also shown in Table 2.

In Example 1, Exemplified Compound No. No. 12 pyromellitic acid diimide-isoindole dimer derivative was exemplified as Compound No. Except that the derivative was changed to the derivative of No. 5, the same procedure as in Example 1 was carried out. 4 was prepared and evaluated.
The results are also shown in Table 2.

In Example 1, Exemplified Compound No. No. 12 pyromellitic acid diimide-isoindole dimer derivative was exemplified as Compound No. Except for the change to the derivative of No. 7, the electrophotographic photoreceptor No. 5 was prepared and evaluated.
The results are also shown in Table 2.

In Example 1, Exemplified Compound No. No. 12 pyromellitic acid diimide-isoindole dimer derivative was exemplified as Compound No. Except that the derivative was changed to the derivative of No. 9, the same procedure as in Example 1 was carried out. 6 was prepared and evaluated.
The results are also shown in Table 2.

In Example 1, Exemplified Compound No. No. 12 pyromellitic acid diimide-isoindole dimer derivative was exemplified as Compound No. Except for the change to the derivative of No. 11, the electrophotographic photoreceptor No. 7 was made and evaluated.
The results are also shown in Table 2.

In Example 1, Exemplified Compound No. No. 12 pyromellitic acid diimide-isoindole dimer derivative was exemplified as Compound No. Except that the derivative was changed to the derivative No. 13, the same procedure as in Example 1 was carried out. 8 was prepared and evaluated.
The results are also shown in Table 2.

In Example 1, Exemplified Compound No. No. 12 pyromellitic acid diimide-isoindole dimer derivative was exemplified as Compound No. Except that the derivative was changed to the derivative of No. 15, the same procedure as in Example 1 was carried out. 9 was made and evaluated.
The results are also shown in Table 2.

In Example 1, Exemplified Compound No. No. 12 pyromellitic acid diimide-isoindole dimer derivative was exemplified as Compound No. Except for the change to the derivative of No. 17, the electrophotographic photoreceptor No. 10 were made and evaluated.
The results are also shown in Table 2.

In Example 1, Exemplified Compound No. No. 12 pyromellitic acid diimide-isoindole dimer derivative was exemplified as Compound No. Except for the change to the derivative of No. 21, the same procedure as in Example 1 was carried out. 11 was made and evaluated.
The results are also shown in Table 2.

In Example 1, Exemplified Compound No. No. 12 pyromellitic acid diimide-isoindole dimer derivative was exemplified as Compound No. Except for the change to the derivative of No. 23, the same procedure as in Example 1 was repeated except that the electrophotographic photoreceptor No. 12 were made and evaluated.
The results are also shown in Table 2.

In Example 1, Exemplified Compound No. No. 12 pyromellitic acid diimide-isoindole dimer derivative was exemplified as Compound No. Except that the derivative was changed to the derivative of No. 25, the same procedure as in Example 1 was carried out. 13 was made and evaluated.
The results are also shown in Table 2.

In Example 1, Exemplified Compound No. No. 12 pyromellitic acid diimide-isoindole dimer derivative was exemplified as Compound No. Except for the change to the derivative of No. 27, the electrophotographic photoreceptor No. 14 was made and evaluated.
The results are also shown in Table 2.

In Example 1, Exemplified Compound No. No. 12 pyromellitic acid diimide-isoindole dimer derivative was exemplified as Compound No. Except for the change to the derivative of No. 29, the same procedure as in Example 1 was carried out, except that the electrophotographic photoreceptor No. 15 was made and evaluated.
The results are also shown in Table 2.

Except that the charge transport layer coating solution in Example 1 was changed to the one having the following composition, the same procedure as in Example 1 was carried out. 16 was produced.
The evaluation was performed in the same manner as in Example 1 except that the charging method was changed to a negatively charged corona discharge (scorotron method). The results are shown in Table 3.

Charge transport layer coating solution / polycarbonate resin (Z Polyca, manufactured by Teijin Chemicals): 10 parts Pyromellitic acid diimide-isoindole dimer derivative of Exemplified Compound 12: 1 part Charge transport material (CTM-1) having the following structural formula ): 9 parts Tetrahydrofuran: 100 parts

In Example 16, Exemplified Compound No. 1 Instead of the 12 pyromellitic acid diimide-isoindole dimer derivative, Exemplified Compound No. 1 except that the pyromellitic acid diimide-isoindole dimer derivative of No. 1 was used. 17 was produced.
The results are also shown in Table 3.

In Example 16, Exemplified Compound No. 1 Instead of the 12 pyromellitic acid diimide-isoindole dimer derivative, Exemplified Compound No. 3 except that the pyromellitic acid diimide-isoindole dimer derivative of No. 3 was used. 18 was produced.
The results are also shown in Table 3.

In Example 16, Exemplified Compound No. 1 Instead of the 12 pyromellitic acid diimide-isoindole dimer derivative, Exemplified Compound No. 5 except that the pyromellitic acid diimide-isoindole dimer derivative of No. 5 was used. 19 was produced.
The results are also shown in Table 3.

In Example 16, Exemplified Compound No. 1 Instead of the 12 pyromellitic acid diimide-isoindole dimer derivative, Exemplified Compound No. Except that the pyromellitic diimide-isoindole dimer derivative of No. 7 was used, the same procedure as in Example 16 was carried out. 20 was produced.
The results are also shown in Table 3.

In Example 16, Exemplified Compound No. 1 Instead of the 12 pyromellitic acid diimide-isoindole dimer derivative, Exemplified Compound No. Except that the pyromellitic acid diimide-isoindole dimer derivative of No. 9 was used, the same procedure as in Example 16 was carried out. 21 was produced.
The results are also shown in Table 3.

In Example 16, Exemplified Compound No. 1 Instead of the 12 pyromellitic acid diimide-isoindole dimer derivative, Exemplified Compound No. Except that the pyromellitic acid diimide-isoindole dimer derivative of No. 11 was used, the same procedure as in Example 16 was carried out. 22 was produced.
The results are also shown in Table 3.

In Example 16, Exemplified Compound No. 1 Instead of the 12 pyromellitic acid diimide-isoindole dimer derivative, Exemplified Compound No. Except for using the pyromellitic acid diimide-isoindole dimer derivative of No. 13 in the same manner as in Example 16, the electrophotographic photoreceptor No. 23 was produced.
The results are also shown in Table 3.

In Example 16, Exemplified Compound No. 1 Instead of the 12 pyromellitic acid diimide-isoindole dimer derivative, Exemplified Compound No. Except for using the pyromellitic acid diimide-isoindole dimer derivative of No. 15 in the same manner as in Example 16, the electrophotographic photoreceptor No. 24 was produced.
The results are also shown in Table 3.

In Example 16, Exemplified Compound No. 1 Instead of the 12 pyromellitic acid diimide-isoindole dimer derivative, Exemplified Compound No. Except for using the pyromellitic acid diimide-isoindole dimer derivative of No. 17 in the same manner as in Example 16, the electrophotographic photoreceptor No. 25 was produced.
The results are also shown in Table 3.

In Example 16, Exemplified Compound No. 1 Instead of the 12 pyromellitic acid diimide-isoindole dimer derivative, Exemplified Compound No. Except for using the pyromellitic acid diimide-isoindole dimer derivative of No. 21 in the same manner as in Example 16, the electrophotographic photoreceptor No. 26 was produced.
The results are also shown in Table 3.

In Example 16, Exemplified Compound No. 1 Instead of the 12 pyromellitic acid diimide-isoindole dimer derivative, Exemplified Compound No. Except for using the pyromellitic acid diimide-isoindole dimer derivative of No. 23, the same procedure as in Example 16 was carried out. 27 was produced.
The results are also shown in Table 3.

In Example 16, Exemplified Compound No. 1 Instead of the 12 pyromellitic acid diimide-isoindole dimer derivative, Exemplified Compound No. Except that the pyromellitic acid diimide-isoindole dimer derivative of 25 was used, the same procedure as in Example 16 was carried out. 28 was produced.
The results are also shown in Table 3.

In Example 16, Exemplified Compound No. 1 Instead of the 12 pyromellitic acid diimide-isoindole dimer derivative, Exemplified Compound No. Except that the pyromellitic acid diimide-isoindole dimer derivative of No. 27 was used, the same procedure as in Example 16 was carried out. 29 was produced.
The results are also shown in Table 3.

In Example 16, Exemplified Compound No. 1 Instead of the 12 pyromellitic acid diimide-isoindole dimer derivative, Exemplified Compound No. Except that the pyromellitic acid diimide-isoindole dimer derivative of No. 29 was used, the same procedure as in Example 16 was carried out. 30 was produced.
The results are also shown in Table 3.

The pyromellitic acid diimide-isoindole dimer derivative and the charge transport material no. An electrophotographic photoreceptor 31 was prepared and evaluated in the same manner as in Example 16 except that the amount of 1 was changed to the following amount.
The results are also shown in Table 4.
-Exemplified Compound No. 1 pyromellitic acid diimide-isoindole dimer derivative: 1 part Charge transport material (CTM-1): 7 parts

The pyromellitic acid diimide-isoindole dimer derivative contained therein is exemplified as Compound No. An electrophotographic photosensitive member 32 was produced and evaluated in the same manner as in Example 31 except that the number was changed to 16.
The results are also shown in Table 4.

The pyromellitic acid diimide-isoindole dimer derivative contained therein is exemplified as Compound No. An electrophotographic photosensitive member 33 was produced and evaluated in the same manner as in Example 31 except that it was changed to 20.
The results are also shown in Table 4.

The pyromellitic acid diimide-isoindole dimer derivative contained therein is exemplified as Compound No. An electrophotographic photoreceptor 32 was produced and evaluated in the same manner as in Example 31 except that the number was changed to 30.
The results are also shown in Table 4.

In Example 31, the electrophotographic photosensitive member No. 1 was changed in the same manner as in Example 31 except that the charge transport material (CTM-1) was changed to the following charge transport material (CTM-2). 35 was made and evaluated.
The results are also shown in Table 5.

In Example 32, the electrophotographic photosensitive member No. 1 was changed in the same manner as in Example 32 except that the charge transport material (CTM-1) was changed to the charge transport material (CTM-2). 36 was made and evaluated.
The results are also shown in Table 5.

In Example 33, the electrophotographic photosensitive member No. 1 was changed in the same manner as in Example 33 except that the charge transport material (CTM-1) was changed to the charge transport material (CTM-2). 37 was made and evaluated.
The results are also shown in Table 5.

In Example 34, except that the charge transport material (CTM-1) was changed to the charge transport material (CTM-2), in the same manner as in Example 34, the electrophotographic photoreceptor No. 38 was made and evaluated.
The results are also shown in Table 5.

In Example 31, except that the charge transport material (CTM-1) was changed to the following charge transport material (CTM-3), the same procedure as in Example 31 was carried out. 39 was made and evaluated.
The results are also shown in Table 6.

In Example 32, except that the charge transport material (CTM-1) was changed to the charge transport material (CTM-3), the same procedure as in Example 32 was performed, except that the electrophotographic photoreceptor No. 40 was made and evaluated.
The results are also shown in Table 6.

In Example 33, except that the charge transport material (CTM-1) was changed to the charge transport material (CTM-3), the same procedure as in Example 33 was carried out. 41 was made and evaluated.
The results are also shown in Table 6.

In Example 34, except that the charge transport material (CTM-1) was changed to the charge transport material (CTM-3), the same procedure as in Example 34 was performed, except that the electrophotographic photoreceptor No. 42 was made and evaluated.
The results are also shown in Table 6.

  In Example 31, an electrophotographic photoreceptor 43 was prepared and evaluated in the same manner as in Example 31 except that the charge transport material (CTM-1) was changed to the following charge transport material (CTM-4). The results are also shown in Table 7.

  In Example 32, an electrophotographic photosensitive member 44 was prepared and evaluated in the same manner as in Example 32 except that the charge transport material (CTM-1) was changed to the charge transport material (CTM-4). The results are also shown in Table 7.

  In Example 33, an electrophotographic photoreceptor 45 was prepared and evaluated in the same manner as in Example 33 except that the charge transport material (CTM-1) was changed to the charge transport material (CTM-4). The results are also shown in Table 7.

  In Example 34, an electrophotographic photoreceptor 46 was prepared and evaluated in the same manner as in Example 34 except that the charge transport material (CTM-1) was changed to the charge transport material (CTM-4). The results are also shown in Table 7.

An electrophotographic photoreceptor 47 was prepared and evaluated in the same manner as in Example 16 except that the charge generation layer coating solution and the charge transport layer coating solution were changed to the following.
The results are also shown in Table 8.

<Manufacture of oxotitanium phthalocyanine>
In the same manner as in Synthesis Example 4 described in JP-A No. 2001-019871, 29.2 g of 1,3-diiminoisoindoline and 200 ml of sulfolane are mixed, and 20.4 g of titanium tetrabutoxide is added dropwise under a nitrogen stream. After completion of the dropwise addition, the temperature was gradually raised to 180 ° C., and the reaction was carried out by stirring for 5 hours while maintaining the reaction temperature between 170 ° C. and 180 ° C. After completion of the reaction, the mixture was allowed to cool, and then the precipitate was filtered, washed with chloroform until the powder turned blue, then washed several times with methanol, further washed several times with hot water at 80 ° C., and dried. Crude titanyl phthalocyanine was obtained. Dissolve the crude titanyl phthalocyanine in 20 times the amount of concentrated sulfuric acid, add dropwise to 100 times the amount of ice water with stirring, filter the precipitated crystals, and then repeat washing with water until the washing solution becomes neutral, wet cake of titanyl phthalocyanine pigment Got. The X-ray diffraction spectrum of the dried cake is shown in FIG. 2 g of the obtained wet cake was put into 20 g of carbon disulfide and stirred for 4 hours. 100 g of methanol was added thereto, and the mixture was stirred for 1 hour, then filtered and dried to obtain oxotitanium phthalocyanine crystal powder.

Charge generation layer coating solution ・ Oxotitanium phthalocyanine having powder XD spectrum shown in FIG. 10: 8 parts Polyvinyl butyral (BX-1): 5 parts 2-butanone: 400 parts ◎ Charge transport layer coating liquid, polycarbonate Resin (Z Polyca): 10 parts 7 pyromellitic acid diimide-isoindole dimer derivative: 1 part Charge transport material (CTM-1) having the following structural formula: 7 parts Toluene: 70 parts

The pyromellitic acid diimide-isoindole dimer derivative in Example 47 was converted to the exemplified compound No. The electrophotographic photoreceptor 48 was produced and evaluated in the same manner except that the number was changed to 30.
The results are also shown in Table 8.

  A photosensitive layer coating solution having the following composition was applied on an aluminum cylinder having a diameter of 100 mm and dried to form a 30 μm single layer photosensitive layer to obtain an electrophotographic photosensitive member. (Photoreceptor No. 49)

[Coating solution for photosensitive layer]
X-type metal-free phthalocyanine (FastogenBlue 8120B: manufactured by Dainippon Ink & Chemicals): 2 parts Charge transport material represented by the following structural formula (CTM-2): 30 parts Pyromellitic acid diimide-isoindole dimer derivative No. 1: 20 parts Bisphenol Z polycarbonate (Panlite TS-2050, manufactured by Teijin Chemicals): 50 parts Tetrahydrofuran: 500 parts

The produced electrophotographic photosensitive member is positively charged with a remodeled imagio Neo 752 made by Ricoh using a corona charging method (scorotron type) as a charging method and a semiconductor laser (LD) having an image exposure light source of 780 nm. After setting to (V), a repeated test equivalent to printing a total of 100,000 sheets was continuously performed. At that time, the initial portion and the bright portion potential (V) image after the repeated test were evaluated. Further, the light potential after the repeated test was also measured. Further, image blur (dot resolution) was evaluated in the same manner as in Example 1.
The evaluation results are shown in Table 9.

The pyromellitic acid diimide-isoindole dimer derivative of Example 49 No. 1 The electrophotographic photosensitive member 50 of the present invention was prepared and evaluated in the same manner except that it was replaced with 16.
Table 9 shows the evaluation results.

The pyromellitic acid diimide-isoindole dimer derivative of Example 49 No. 1 The electrophotographic photosensitive member 51 of the present invention was prepared and evaluated in the same manner except that it was replaced with 20.
Table 9 shows the evaluation results.

The pyromellitic acid diimide-isoindole dimer derivative of Example 49 No. 1 The electrophotographic photosensitive member 52 of the present invention was prepared and evaluated in the same manner except that it was replaced with 30.
Table 9 shows the evaluation results.

The same photosensitive layer coating solution as in Example 49 was applied onto an aluminum cylinder with a diameter of 30 mm and dried to form a 30 μm single-layer photosensitive layer to obtain an electrophotographic photosensitive member (photosensitive member No. 53). ).
Further, the photoreceptor was evaluated in the same manner as in Example 16.
The results are shown in Table 10.

The pyromellitic acid diimide-isoindole dimer derivative No. 53 of Example 53 No. 1 The electrophotographic photosensitive member 54 of the present invention was prepared and evaluated in the same manner except that it was replaced with 16.
The results are shown in Table 10.

The pyromellitic acid diimide-isoindole dimer derivative No. 53 of Example 53 No. 1 The electrophotographic photosensitive member 55 of the present invention was prepared and evaluated in the same manner except that it was replaced with the one of 20.
The results are shown in Table 10.

The pyromellitic acid diimide-isoindole dimer derivative No. 53 of Example 53 No. 1 The electrophotographic photosensitive member 56 of the present invention was prepared and evaluated in the same manner except that it was replaced with 30.
The results are shown in Table 10.

A 20 μm charge transport layer and a 0.1 μm charge generation layer are formed by sequentially applying and drying a charge transport layer coating liquid and a charge generation layer coating liquid having the following composition on an aluminum cylinder having a diameter of 30 mm. Then, an electrophotographic photosensitive member was produced (photosensitive member No. 57) and evaluated in the same manner as in Example 53.
The evaluation results are shown in Table 11.

[Composition of coating solution for charge transport layer]
Bisphenol A polycarbonate (Panlite C-1400, manufactured by Teijin Chemicals): 10 parts Toluene: 100 parts Pyromellitic acid diimide-isoindole dimer derivative No. 1:10 parts [composition of charge generation layer coating solution]
・ Polyvinyl butyral (XYHL, manufactured by UCC): 0.5 part ・ Cyclohexanone: 200 parts ・ Methyl ethyl ketone: 80 parts ・ X-type metal-free phthalocyanine (FastogenBlue 8120B: manufactured by Dainippon Ink and Chemicals): 2 parts

The pyromellitic acid diimide-isoindole dimer derivative No. No. 1 The electrophotographic photosensitive member 58 of the present invention was prepared and evaluated in the same manner except that it was replaced with 16.
The evaluation results are shown in Table 11.

The pyromellitic acid diimide-isoindole dimer derivative No. No. 1 The electrophotographic photosensitive member 59 of the present invention was prepared and evaluated in the same manner except that it was replaced with 20.
The evaluation results are shown in Table 11.

The pyromellitic acid diimide-isoindole dimer derivative No. No. 1 The electrophotographic photosensitive member 60 of the present invention was prepared and evaluated in the same manner except that it was replaced with 30.
The evaluation results are shown in Table 11.

Evaluation was carried out in the same manner except that the charging system in Example 1 was replaced with a negatively charged corona discharge (scorotron system).
The results are shown in Table 12.

In Example 61, Exemplified Compound No. No. 12 pyromellitic acid diimide-isoindole dimer derivative was exemplified as Compound No. Evaluation was conducted in the same manner as in Example 61 except that the derivative was changed to 1 derivative.
The results are also shown in Table 12.

In Example 61, Exemplified Compound No. No. 12 pyromellitic acid diimide-isoindole dimer derivative was exemplified as Compound No. Evaluation was conducted in the same manner as in Example 61 except that the derivative was changed to the derivative of 3.
The results are also shown in Table 12.

In Example 61, Exemplified Compound No. No. 12 pyromellitic acid diimide-isoindole dimer derivative was exemplified as Compound No. Evaluation was conducted in the same manner as in Example 61 except that the derivative was changed to the derivative of No. 5.
The results are also shown in Table 12.

In Example 61, Exemplified Compound No. No. 12 pyromellitic acid diimide-isoindole dimer derivative was exemplified as Compound No. Evaluation was conducted in the same manner as in Example 61 except that the derivative was changed to the derivative of No. 7.
The results are also shown in Table 12.

In Example 61, Exemplified Compound No. No. 12 pyromellitic acid diimide-isoindole dimer derivative was exemplified as Compound No. Evaluation was conducted in the same manner as in Example 61 except that the derivative was changed to 9 derivative.
The results are also shown in Table 12.

In Example 61, Exemplified Compound No. No. 12 pyromellitic acid diimide-isoindole dimer derivative was exemplified as Compound No. Evaluation was conducted in the same manner as in Example 61 except that the derivative was changed to 11 derivatives.
The results are also shown in Table 12.

In Example 61, Exemplified Compound No. No. 12 pyromellitic acid diimide-isoindole dimer derivative was exemplified as Compound No. Evaluation was conducted in the same manner as in Example 61 except that the derivative was changed to 13 derivatives.
The results are also shown in Table 12.

In Example 61, Exemplified Compound No. No. 12 pyromellitic acid diimide-isoindole dimer derivative was exemplified as Compound No. Evaluation was conducted in the same manner as in Example 61 except that the derivative was changed to 15 derivatives.
The results are also shown in Table 12.

In Example 61, Exemplified Compound No. No. 12 pyromellitic acid diimide-isoindole dimer derivative was exemplified as Compound No. Evaluation was conducted in the same manner as in Example 61 except that the derivative was changed to 17 derivative.
The results are also shown in Table 12.

In Example 61, Exemplified Compound No. No. 12 pyromellitic acid diimide-isoindole dimer derivative was exemplified as Compound No. Evaluation was conducted in the same manner as in Example 61 except that the derivative was changed to 21.
The results are also shown in Table 12.

In Example 61, Exemplified Compound No. No. 12 pyromellitic acid diimide-isoindole dimer derivative was exemplified as Compound No. Evaluation was conducted in the same manner as in Example 61 except that the derivative was changed to 23.
The results are also shown in Table 12.

In Example 61, Exemplified Compound No. No. 12 pyromellitic acid diimide-isoindole dimer derivative was exemplified as Compound No. Evaluation was conducted in the same manner as in Example 61 except that the derivative was changed to 25.
The results are also shown in Table 12.

In Example 61, Exemplified Compound No. No. 12 pyromellitic acid diimide-isoindole dimer derivative was exemplified as Compound No. Evaluation was conducted in the same manner as in Example 61 except that the derivative was changed to 29.
The results are also shown in Table 12.

In Example 61, Exemplified Compound No. No. 12 pyromellitic acid diimide-isoindole dimer derivative was exemplified as Compound No. Evaluation was conducted in the same manner as in Example 61 except that the derivative was changed to 33.
The results are also shown in Table 12.

Except that the charge transport layer coating solution in Example 16 was changed to the one having the following composition, the same procedure as in Example 16 was carried out. 61 was produced.
The evaluation was performed in the same manner except that the charging system in Example 16 was replaced with a positively charged corona discharge (scorotron system).
The results are also shown in Table 13.

Charge transport layer coating solution / polycarbonate resin (Z Polyca, manufactured by Teijin Chemicals): 10 parts Pyromellitic acid diimide-isoindole dimer derivative of Exemplified Compound 8: 1 part Charge transport material (CTM-5) having the following structural formula ): 9 parts Tetrahydrofuran: 100 parts

Except that the charge transporting material in Example 76 was changed to a charge transporting material (CTM-6) having the following structural formula, the same procedure as in Example 76 was followed. 62 was produced.
All evaluations were made in the same manner as in Example 61.
The results are also shown in Table 13.

Except that the charge transport material (CTM-5) in Example 76 was changed to a charge transport material (CTM-7) having the following structural formula, the same procedure as in Example 76 was followed to obtain an electrophotographic photoreceptor No. 63 was produced.
All evaluations were made in the same manner as in Example 61.
The results are also shown in Table 13.

Except that the charge transport material (CTM-5) in Example 76 was changed to a charge transport material (CTM-8) having the following structural formula, the same procedure as in Example 76 was followed to obtain an electrophotographic photoreceptor No. 64 was produced.
All evaluations were made in the same manner as in Example 61.
The results are also shown in Table 13.

[Comparative Example 1]
In Example 1, pyromellitic acid diimide-isoindole dimer derivative no. Except for changing the benzoquinone derivative (CTM-8) to the following benzoquinone derivative (CTM-8), the same procedure as in Example 1 was followed. 1 was made and evaluated. The results are shown in Table 14.

[Comparative Example 2]
In Example 16, comparison was made in the same manner as in Example 16 except that the pyromellitic acid diimide-isoindole dimer derivative was not added to the charge transport layer forming coating solution and the weight of the charge transport material was 10 parts. Electrophotographic photoreceptor No. 2 was prepared and evaluated. The results are shown in Table 14.

[Comparative Example 3]
In Example 35, except that the pyromellitic acid diimide-isoindole dimer derivative was changed to the following tetraphenylmethane compound (CTM-9) (described in JP-A No. 2000-231204), all were the same as in Example 35, Comparative electrophotographic photoreceptor No. 3 was made and evaluated.
The results are shown in Table 14.

[Comparative Example 4]
In Example 47, except that the pyromellitic acid diimide-isoindole dimer derivative was changed to the following polyaryl ring amine (CTM-10), the same procedure as in Example 47 was carried out. 4 was prepared and evaluated. The results are shown in Table 14.

[Comparative Example 5]
In Example 49, pyromellitic acid diimide-isoindole dimer derivative no. Comparative electrophotographic photosensitive member No. 1 was prepared in the same manner as in Example 49 except that 1 and 20 parts were changed to the following electron transport material (CTM-11). 5 was prepared and evaluated in the same manner. The results are shown in Table 14.
-Charge transport material represented by the following structural formula: 18 parts

-Charge transport material represented by the following structural formula (CTM-12): 2 parts

[Comparative Example 6]
In Example 49, pyromellitic acid diimide-isoindole dimer derivative no. Comparative electrophotographic photosensitive member No. 1 was prepared in the same manner as in Example 49 except that 1 and 20 parts were changed to the following electron transport materials. 6 was prepared and evaluated in the same manner. The results are shown in Table 14.
-Charge transport material represented by the following structural formula (CTM-13): 20 parts

[Comparative Example 7]
In Example 57, pyromellitic acid diimide-isoindole dimer derivative no. Comparative electrophotographic photosensitive member No. 1 was prepared in the same manner as in Example 57 except that 1 and 10 parts were used as the following electron transport materials. 7 was prepared and evaluated in the same manner. The results are shown in Table 14.
-Charge transport material represented by the following structural formula (CTM-11): 9 parts

・下記構造式で表わされる電荷輸送物質（ＣＴＭ−１２）：１部

-Charge transport material represented by the following structural formula (CTM-12): 1 part

From the above evaluation results, it was confirmed that the bright part potential increase was small even after printing 100,000 sheets, and that the photoconductor containing the pyromellitic acid diimide-isoindole dimer derivative of the present invention can stably obtain a high-quality image. It was.
On the other hand, the comparative photoconductors 1, 3, and 4 have a very high bright portion potential from the beginning, causing a decrease in image density and a decrease in resolution, and the gradation is significantly decreased after printing 100,000 sheets. Image discrimination was impossible.
Further, from the evaluation results of Tables 2 and 10, the photoreceptor of the present invention can obtain a good image even in the positive charging system, and the image quality is good even after printing 100,000 sheets, and the image blur (dot resolution) evaluation result. Was also good.
Further, although the comparative photoconductors 2, 5, 6, and 7 have a relatively small increase in the bright portion potential, the resolution decrease due to repeated use is large as compared with the photoconductor of the present invention.

Further, the electrophotographic photoreceptor 1 of the present invention was left in a desiccator adjusted to a nitrogen oxide (NOx) gas concentration of 50 ppm for 4 days, and image evaluation was performed before and after.
The results are shown in Table 15.

Similarly, the electrophotographic photosensitive member 17 of the present invention was left in a desiccator adjusted to a nitrogen oxide (NOx) gas concentration of 50 ppm for 4 days, and image evaluation was performed before and after.
The results are shown in Table 15.

Similarly, the electrophotographic photoreceptor 33 of the present invention was left in a desiccator adjusted to a nitrogen oxide (NOx) gas concentration of 50 ppm for 4 days, and image evaluation was performed before and after.
The results are shown in Table 15.

Similarly, the electrophotographic photoreceptor 37 of the present invention was left for 4 days in a desiccator adjusted to a nitrogen oxide (NOx) gas concentration of 50 ppm, and image evaluation was performed before and after.
The results are shown in Table 15.

Similarly, the electrophotographic photoreceptor 48 of the present invention was left for 4 days in a desiccator adjusted to a nitrogen oxide (NOx) gas concentration of 50 ppm, and image evaluation was performed before and after.
The results are shown in Table 15.

Similarly, the electrophotographic photosensitive member 49 of the present invention was left in a desiccator adjusted to a nitrogen oxide (NOx) gas concentration of 50 ppm for 4 days, and image evaluation was performed before and after.
The results are shown in Table 15.

Similarly, the electrophotographic photoreceptor 59 of the present invention was left in a desiccator adjusted to a nitrogen oxide (NOx) gas concentration of 50 ppm for 4 days, and image evaluation was performed before and after.
The results are shown in Table 15.

[Comparative Example 8]
Similarly, the comparative photoconductor 2 was left in a desiccator adjusted to a nitrogen oxide (NOx) gas concentration of 50 ppm for 4 days to perform image evaluation before and after.
The results are shown in Table 15.

From the evaluation results of Table 15, it can be seen that the resistance to oxidizing gas, that is, the suppression of reduction in resolution, is greatly improved by incorporating the pyromellitic diimide-isoindole dimer derivative of the present invention into the photoreceptor.
On the other hand, the comparative photoconductor 2 has good initial image quality, but it can be seen that the resolution is significantly reduced by the oxidizing gas.

DESCRIPTION OF SYMBOLS 1 Photoconductor 2 Static elimination lamp 3 Charger charger 4 Eraser 5 Image exposure part 6 Developing unit 7 Charger before transfer 8 Registration roller 9 Transfer paper 10 Transfer charger 11 Separation charger 12 Separation nail 13 Charger before cleaning 14 Fur brush 15 Cleaning blade 16 Photoconductor 17 Charging Charger 18 Cleaning Brush 19 Image Exposure Unit 20 Developing Roller 21 Photoconductor 22a Drive Roller 22b Drive Roller 23 Charger Charger 24 Image Exposure Source 25 Transfer Charger 26 Pre-Cleaning Exposure 27 Cleaning Brush 28 Static Electricity Light Source 31 Conductive Support 33 Photosensitive Layer 35 charge generation layer 37 charge transport layer 39 protective layer

Japanese Patent No. 2732697 JP 2000-231204 A JP-A-60-196768 Japanese Patent No. 2884353 JP 2004-258253 A

(Itami et al., Konica Technical Report, 13, 37, 2000) D. W. Jones, Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry, 21, 2728 (1972)

Claims (19)

An electrophotographic photoreceptor having at least a photosensitive layer on a conductive support, wherein the photosensitive layer contains a pyromellitic acid diimide-isoindole dimer derivative represented by the following general formula (1). An electrophotographic photosensitive member characterized by the above.

[Wherein R1, R2, R3, R4, R5, R6, R7 represent a hydrogen atom, a substituted or unsubstituted alkyl group, an alkoxy group, a substituted or unsubstituted aromatic hydrocarbon group, a halogen atom, or a nitro group. These may be the same or different. I and j are integers of 1 to 4, k, l, m, and n are integers of 1 to 5, and o is an integer of 1 or 2.   2. The electrophotographic photosensitive member according to claim 1, wherein the electrophotographic photosensitive member is charged to both positive and negative polarities.   The electrophotographic photosensitive member according to claim 1, wherein the photosensitive layer further contains a charge transport material. The electrophotographic photosensitive member according to claim 3, wherein the charge transport material is a derivative represented by the following general formula (2).

[Wherein, X represents a single bond or a vinylene group, R 4 represents a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aromatic hydrocarbon group, and Ar 1 represents a substituted or unsubstituted aromatic group. Represents a hydrocarbon group, R5 represents a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aromatic hydrocarbon group, and Ar1 and R5 may form a ring together. A represents general formula (3), general formula (4), a 9-anthryl group, or a substituted or unsubstituted carbazolyl group.

(Here, R6 represents a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, or general formula (5).)

Wherein R7 and R8 represent a substituted or unsubstituted alkyl group or a substituted or unsubstituted aromatic hydrocarbon group, and R7 and R8 may be the same or different and may form a ring. , M represents an integer of 1 to 3, and when it is 2 or more, R6 may be the same or different. ] The electrophotographic photosensitive member according to claim 3, wherein the charge transport material is a derivative represented by the following general formula (6).

[Wherein R9, R11 and R12 are a hydrogen atom, an amino group, an alkoxy group, a thioalkoxy group, an aryloxy group, a methylenedioxy group, a substituted or unsubstituted alkyl group, a halogen atom or a substituted or unsubstituted aromatic group. In the hydrocarbon group, R10 represents a hydrogen atom, an alkoxy group, a substituted or unsubstituted alkyl group or a halogen atom. K, l, m and n are integers of 1, 2, 3 or 4, and when each is an integer of 2, 3 or 4, R9, R10, R11 and R12 may be the same or different. Good. ] The electrophotographic photosensitive member according to claim 3, wherein the charge transport material is a derivative represented by the following general formula (7).

[Wherein, X represents a single bond or a vinylene group, R13 and R14 represent a hydrogen atom, a substituted or unsubstituted alkyl group or a substituted or unsubstituted aromatic hydrocarbon group, and Ar3 represents a substituted or unsubstituted aromatic group. Represents a group hydrocarbon group, Ar 3 and R 13 may form a ring together. Ar2 represents the following general formula (8) or general formula (9).

(Here, R6 represents a hydrogen atom, an alkyl group, an alkoxy group, or a halogen atom, m represents an integer of 1 to 3, and when R2 is 2 or more, R6 may be the same or different. R7 may be substituted or unsubstituted. Represents an alkyl group or a substituted or unsubstituted aromatic hydrocarbon group.]] The electrophotographic photosensitive member according to claim 3, wherein the charge transport material is a derivative represented by the following general formula (10).

[Wherein, X represents a single bond or a vinylene group, R15 and R16 represent a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aromatic hydrocarbon group, and Ar4 represents a substituted or unsubstituted 2 group. Represents a divalent aromatic hydrocarbon group, and A represents a general formula (3), a general formula (4), a 9-anthryl group, or a substituted or unsubstituted carbazolyl group.

(Here, R6 represents a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, or general formula (5).)

Wherein R7 and R8 represent a substituted or unsubstituted alkyl group or a substituted or unsubstituted aromatic hydrocarbon group, and R7 and R8 may be the same or different and may form a ring. , M represents an integer of 1 to 3, and when 2 or more, R may be the same or different. ] 4. The electrophotographic photosensitive member according to claim 3, wherein the charge transport material is a derivative represented by the following general formula (14).

(In the formula, R17 and R18 represent a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aromatic hydrocarbon group, which may be the same or different.) 4. The electrophotographic photoreceptor according to claim 3, wherein the charge transport material is a derivative represented by the following general formula (15).

[Wherein R19 represents an alkyl group which may have a substituent or an aryl group which may have a substituent, and R20 has an alkyl group which may have a substituent or a substituent. Or a group represented by the following general formula (16):

(In the formula, R21 represents an alkyl group which may have a substituent or an aryl group which may have a substituent.) 4. The electrophotographic photoreceptor according to claim 3, wherein the charge transport material is a derivative represented by the following general formula (17).

(Wherein R22 and R23 each represent a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aromatic hydrocarbon group, which may be the same or different.) The electrophotographic photosensitive member according to claim 3, wherein the charge transport material is a derivative represented by the following general formula (18).

(In the formula, R24 and R25 each represents a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aromatic hydrocarbon group, which may be the same or different.)   The electrophotographic photosensitive member according to claim 1, wherein the photosensitive layer is formed by sequentially laminating at least a charge generation layer and a charge transport layer.   The electrophotographic photosensitive member according to claim 1, wherein the photosensitive layer is formed by sequentially laminating at least a charge transport layer and a charge generation layer.   The electrophotographic photosensitive member according to claim 1, wherein the photosensitive layer is a single-layer type photosensitive layer.   An electrophotographic method in which at least charging, image exposure, development, and transfer are repeatedly performed on an electrophotographic photosensitive member, wherein the electrophotographic photosensitive member is the electrophotographic photosensitive member according to any one of claims 1 to 14. An electrophotographic method characterized by the above.   Digital electrophotography in which at least charging, image exposure, development, and transfer are repeated on the electrophotographic photosensitive member, and an electrostatic latent image is written on the photosensitive member by an LD or LED during image exposure. 15. An electrophotographic method, wherein the electrophotographic photosensitive member is the electrophotographic photosensitive member according to any one of claims 1 to 14.   15. An electrophotographic apparatus comprising at least a charging means, an image exposure means, a developing means, a transfer means, and an electrophotographic photosensitive member, wherein the electrophotographic photosensitive member is an electrophotographic photosensitive member according to any one of claims 1 to 14. An electrophotographic apparatus characterized by being a body.   An electrophotographic apparatus comprising at least a charging unit, an image exposing unit, a developing unit, a transferring unit, and an electrophotographic photosensitive member, wherein an electrostatic latent image is formed on the photosensitive member by using an LD or an LED as the image exposing unit. 15. A digital electrophotographic apparatus in which an image is written, wherein the electrophotographic photoreceptor is the electrophotographic photoreceptor according to any one of claims 1 to 14.   An electrophotographic photosensitive member comprising at least an electrophotographic photosensitive member, wherein the electrophotographic photosensitive member is the electrophotographic photosensitive member according to any one of claims 1 to 14. Process cartridge for equipment.

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