JP2867741B2 - Electrophotographic photoreceptor for liquid development - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an electrophotographic photosensitive member for liquid development, and more particularly to an electrophotographic photosensitive member for liquid development having excellent solvent resistance.

[0002]

2. Description of the Related Art Conventionally, as a photosensitive material for an electrophotographic photosensitive member (hereinafter referred to as a photosensitive member), an inorganic photoconductive material such as selenium or a selenium alloy, or an inorganic photoconductive material such as zinc oxide or cadmium sulfide is used. Those dispersed in a binder, organic photoconductive substances such as poly-N-vinylcarbazole or polyvinylanthracene, and organic photoconductive substances such as a phthalocyanine compound or a disazo compound dispersed in a resin binder, Vacuum-deposited materials are used.

A photoreceptor is required to have a function of retaining a surface charge in a dark place, a function of receiving light to generate a charge, and a function of receiving light and transporting a charge. A so-called single-layer type photoreceptor that combines these functions with a layer, and a layer that separates functions into a layer that mainly contributes to charge generation and a layer that contributes to charge retention and surface charge retention in the dark and charge transport during photoreception. There is a so-called laminated type photoreceptor in which are laminated. For image formation by electrophotography using these photoconductors, for example, the Carlson method is applied. Image formation by this method involves charging a photoreceptor by corona discharge in a dark place, forming an electrostatic latent image such as a character or picture of an original on the charged photoreceptor surface, and forming the electrostatic latent image Developing with a toner powder or a developer containing toner, and fixing the developed toner image to a support such as paper, the photoreceptor after transfer of the toner image was subjected to static elimination, removal of residual toner, light static elimination, etc. Later, it is used again.

In recent years, many applications of photoconductive organic compounds having excellent charge transporting ability to photoreceptors have been proposed due to their advantages such as flexibility, thermal stability, and film forming properties. For example, oxadiazole compounds include US Pat.
No. 7, Japanese Patent Publication No. 59-2 as a pyrazoline compound
No. 023, and Japanese Patent Publication No. Sho 5
Various charge transporting materials are known from JP-A-5-42380, JP-A-57-101844, JP-A-54-150128 and JP-A-58-180443 as stilbene compounds.

Further, since these photoconductive organic compounds are formed as an organic photoconductive layer on a conductive substrate, a polycarbonate resin, a polyester resin, a polyamide resin, a polyurethane resin, an epoxy resin, a silicon resin, and a methacrylate ester are used. Various binders are known, such as a resin in which a coalescence and a copolymer are used alone or in an appropriate combination.

[0006]

As described above, an organic material has many advantages that an inorganic material does not have, but at the same time, a material that sufficiently satisfies all the characteristics required for an electrophotographic photosensitive member can be obtained. At present, there is a problem in durability when the photosensitive member is used in a liquid developing system in which the photosensitive member is brought into contact with or immersed in a solvent. Solvents used in liquid-developing developing solutions are organic solvents such as alkanes and ketones. However, conventional binders for organic photoconductive layers are softened when they are brought into contact with or dipped in these organic solvents. However, durability such as swelling, cracking and dissolution occurred. An object of the present invention is to provide an electrophotographic photoreceptor having excellent reliability in a liquid developing system by using a substance having excellent solvent resistance for an organic photoconductive layer.

[0007]

According to the present invention, there is provided an electrophotographic photoreceptor for liquid development, comprising a charge generation layer and a charge transport layer on a conductive substrate, wherein the charge generation layer comprises a charge generation layer. The charge transport layer is a layer containing a generating substance, and is achieved by including a poly (alkane diacid 2,6-dimethoxyanthracene-9,10-diol ester) resin represented by the chemical formula (I).

[0008]

Embedded image (Here, m is an integer of 1 or more, n is 100 to 400, and the ratio of the weight average molecular weight to the number average molecular weight is 3 to 5.)

[0009]

The poly (alkane diacid 2,6-dimethoxyanthracene-9,10-diol ester) resin in the present invention is a kind of polyester resin, has a high solvent resistance, and is used in a liquid developing type developer. Since the solvent does not cause phenomena such as softening, swelling, cracking and dissolution, it is suitable as a liquid developing type electrophotographic photoconductor. In addition, the poly (alkanedioic acid 2,6-
Since dimethoxyanthracene-9,10-diol ester) resin has a dimethoxyanthracene structure in its molecular structure and has reduced crystallinity, its solvent resistance is slightly lower than that of a general polyester resin such as ethylene polyterephthalate resin. However, since it is dissolved in a very limited specific solvent, coating-type production is possible.

However, those having a number-average degree of polymerization of less than 100 are unsuitable because peeling and cracking occur due to insufficient flexibility of the coating film and severe shrinkage upon drying. This is considered to be because the degree of freedom of the molecular chain is too large. On the other hand, when the number average degree of polymerization exceeds 400, the solubility in a solvent is too low, so that it is difficult to prepare a coating solution, which is inappropriate. This is considered to be because the degree of freedom of the molecular chain is too small. For the weight average molecular weight to number average molecular weight ratio, those with a ratio less than 3 are:
Similar to those having a number-average degree of polymerization of less than 100, the coating film is insufficient in flexibility and shrinks sharply during drying, so that peeling, cracking, etc. occur, which is inappropriate.

On the other hand, if the ratio exceeds 5, the cause is not clear, but the absolute value of the residual potential at the time of producing the photoreceptor tends to be not sufficiently reduced, and is unsuitable. Further, the dimethoxyanthracene structure imparts a charge transporting capability to the resin itself, and there is no need to separately add a charge transporting substance. Therefore, there is no problem that the charge transporting substance is eluted in the developer. Thus, in the present invention, poly (alkane diacid 2,6)
-Dimethoxyanthracene-9,10-diol ester) resin is soluble in a very limited specific solvent. Although this makes it possible to prepare a coating solution, it has both solvent resistance to the liquid developing type developing solution, and a high curing temperature, long curing time, and a short service life of the thermosetting resin. The above-mentioned disadvantages have been solved, and an unconventional electrophotographic photoreceptor for liquid development has been obtained which has a resin itself having a charge transporting ability.

[0012]

1 is a sectional view showing an electrophotographic photoreceptor for liquid development according to an embodiment of the present invention, wherein 1 is a conductive substrate, 2 is an organic photoconductive layer, 3 is a charge generation layer, and 4 is a charge transport. Layer.
The conductive substrate 1 serves as an electrode of the photoreceptor and serves as a support for the other layers, and may be cylindrical, plate-like, or film-like. The material may be aluminum, stainless steel, nickel, or the like. A material obtained by performing a conductive treatment on metal, glass, resin, or the like may be used. The charge generation layer 3, which is a layer constituting the organic photoconductive layer 2, is formed by depositing and sublimating an organic photoconductive substance or applying a material in which particles of the organic photoconductive substance are dispersed in a resin. It is formed and receives light to generate a charge. In addition, it is important that the charge generation efficiency is high, and at the same time, the injected property of the generated charge into the charge transport layer 4 is important. As the charge generating substance, phthalocyanine pigments, bisazo pigments, polycyclic quinone pigments and the like are used,
A suitable substance can be selected according to the light wavelength range of the exposure light source used for image formation. Since the charge generation layer only needs to have a charge generation function, its thickness is determined by the light absorption coefficient of the charge generation substance and is generally 5 μm or less, preferably 1 μm or less. As the binder, a polycarbonate resin, a polyester resin, a polyamide resin, a polyurethane resin, an epoxy resin, a silicone resin, a polymer and a copolymer of a methacrylate ester alone or
It can be used as a resin in an appropriate combination.

The charge transport layer 4, which is a layer constituting the organic photoconductive layer 2, is a coating film made of poly (alkane diacid 2,6-dimethoxyanthracene-9,10-diol ester) resin and is used in a dark place. In this case, a charge of the photoreceptor is retained as an insulator layer, and a function of transporting charge injected from the charge generation layer during photoreception is exhibited. FIG. 2 is a sectional view showing an electrophotographic photosensitive member for liquid development according to another embodiment of the present invention. 5 is a charge transport layer comprising a polymeric charge transport agent, 6 is poly (alkane diacid 2,6-dimethoxyanthracene-).
9,10-diol ester) resin.

As the polymer charge transporting agent, polyvinyl carbazole, polysilane and the like can be used. FIG. 3 is a sectional view showing an electrophotographic photosensitive member for liquid development according to still another embodiment of the present invention. Reference numeral 7 denotes a charge transport layer composed of a low molecular charge transport agent and a resin, and reference numeral 6 denotes a charge transport layer composed of a poly (alkane diacid 2,6-dimethoxyanthracene-9,10-diol ester) resin.

Various materials such as pyrazoline compounds, hydrazone compounds and stilbene compounds are known as low molecular charge transport agents. As the resin, various materials such as a polycarbonate resin, a polyester resin, a polyamide resin, a polyurethane resin, an epoxy resin, a silicone resin, and a resin in which polymers and copolymers of methacrylic acid esters are used alone or in an appropriate combination are known.

The poly (alkane diacid 2,6-dimethoxyanthracene-9,10-diol ester) resin can be synthesized by polymerizing the corresponding reduced form of dimethoxyanthraquinone with the corresponding alkane diacid. For example, poly (2,6-dimethoxyanthracene dodecanedioate)
The 9,10-diol) resin is hydrosulfite (Wako Pure Chemical Industries, Ltd.) obtained by methoxylating anthraflavic acid (Aldrich Chemical Co., USA) with dimethyl sulfate (Wako Pure Chemical Industries, Ltd.) to obtain 2,6-dimethoxyanthraquinone. Reduced by a reducing agent such as Kogyo Kogyo Co., Ltd., and dodecane diacid dichloride (Aldrich, USA)
Chemical Co., Ltd.). Specific examples of the present invention are shown below, but the present invention is not limited to these examples.

Example 1 60 parts by weight of a metal-free phthalocyanine and 40 parts by weight of a polymethyl methacrylate resin were well mixed and dispersed with 1,000 parts by weight of tetrahydrofuran by a mixer for 3 hours to obtain a coating liquid. This coating solution was applied on an aluminum-evaporated polyester film substrate with a wire bar to form a charge generation layer having a thickness of about 0.5 μm after drying. On the thus-obtained charge generation layer, a poly (nonanedioic acid 2,6-dimethoxyanthracene-9,1) having a number average polymerization degree of 100 and a weight average molecular weight to number average molecular weight ratio of 3 was formed as a charge transport layer.
A coating solution composed of 20 parts by weight of (0-diol ester) resin and 280 parts by weight of tetrachloroethylene was applied by a wire bar, and a charge transport layer having a thickness of 20 μm after drying was formed to prepare a photoreceptor.

Example 2 Instead of a poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a number average degree of polymerization of 100, poly (nonanedioic acid 2,6) having a number average degree of polymerization of 200 was used. -Dimethoxyanthracene-9,10-diol ester) resin was prepared in the same manner as in Example 1 except that a resin was used.

Example 3 Instead of a poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a number average degree of polymerization of 100, a poly (nonanedioic acid 2,6 having a number average degree of polymerization of 300) was used. -Dimethoxyanthracene-9,10-diol ester) resin was prepared in the same manner as in Example 1 except that a resin was used.

Example 4 Instead of a poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a number average polymerization degree of 100, poly (nonanedioic acid 2,6) having a number average polymerization degree of 400 was used. -Dimethoxyanthracene-9,10-diol ester) resin was prepared in the same manner as in Example 1 except that a resin was used.

Comparative Example 1 Instead of a poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a number average polymerization degree of 100, a poly (nonanedioic acid 2,50) having a number average polymerization degree of 50 was used.
A photoconductor was prepared in the same manner as in Example 1 except that (6-dimethoxyanthracene-9,10-diol ester) resin was used.

Comparative Example 2 Instead of a poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a number average degree of polymerization of 100, poly (nonanedioic acid 2,6) having a number average degree of polymerization of 450 was used. A photoreceptor was prepared in the same manner as in Example 1 except that a resin (-dimethoxyanthracene-9,10-diol ester) was used, but poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) was used. ) A sufficient concentration could not be obtained due to poor solubility of the resin, and a film thickness of 20 μm could not be obtained.

The appearances of Examples 1 to 4 thus produced and Comparative Example 1 were compared. Table 1 shows the results.

[0024]

[Table 1]

As can be seen from Table 1, each of the examples has a good glossy appearance, but cracks occur in Comparative Example 1, and a predetermined film thickness is obtained in Comparative Example 2 as described above. Could not be obtained.

Example 5 Instead of a poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a number average degree of polymerization of 100, a poly (decaneedioic acid 2,6 having a number average degree of polymerization of 100) was used. -Dimethoxyanthracene-9,10-diol ester) resin was prepared in the same manner as in Example 1 except that a resin was used.

Example 6 Instead of a poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a number average degree of polymerization of 100, a poly (decaneedioic acid 2,6 having a number average degree of polymerization of 200) was used. -Dimethoxyanthracene-9,10-diol ester) resin was prepared in the same manner as in Example 1 except that a resin was used.

Example 7 Instead of a poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a number average degree of polymerization of 100, poly (decandioic acid 2,6 having a number average degree of polymerization of 300) was used. -Dimethoxyanthracene-9,10-diol ester) resin was prepared in the same manner as in Example 1 except that a resin was used.

Example 8 Instead of a poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a number average degree of polymerization of 100, a poly (decaneedioic acid 2,6 having a number average degree of polymerization of 400) was used. -Dimethoxyanthracene-9,10-diol ester) resin was prepared in the same manner as in Example 1 except that a resin was used.

Comparative Example 3 Instead of a poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a number average degree of polymerization of 100, a poly (decaneedioic acid 2,50) having a number average degree of polymerization of 50 was used.
A photoconductor was prepared in the same manner as in Example 1 except that (6-dimethoxyanthracene-9,10-diol ester) resin was used.

COMPARATIVE EXAMPLE 4 Instead of a poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a number average degree of polymerization of 100, a poly (decaneedioic acid 2,6 having a number average degree of polymerization of 450) was used. -Dimethoxyanthracene-9,10-diol ester) was prepared in the same manner as in Example 1 except that a resin was used, but poly (decaneedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) was used. ) A sufficient concentration could not be obtained due to poor solubility of the resin, and a film thickness of 20 μm could not be obtained. The appearances of Examples 5 to 8 and Comparative Example 3 thus produced were compared. Table 2 shows the results.

[0032]

[Table 2]

As can be seen from Table 2, each of the examples has a good glossy appearance, but cracks occur in Comparative Example 3, and a predetermined film thickness is obtained in Comparative Example 4 as described above. Could not be obtained.

Example 9 Poly (undecandioic acid 2,6 having a number average degree of polymerization of 100) was used instead of the poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a number average degree of polymerization of 100. -Dimethoxyanthracene-9,10-diol ester) resin was prepared in the same manner as in Example 1 except that a resin was used.

Example 10 Instead of a poly (2,6-dimethoxyanthracene-9,10-diol ester) resin having a number average degree of polymerization of 100, poly (undecandioic acid 2,6 having a number average degree of polymerization of 200) was used. -Dimethoxyanthracene-9,10-diol ester) resin was prepared in the same manner as in Example 1 except that a resin was used.

Example 11 Poly (undecandioic acid 2,6 having a number average degree of polymerization of 300) was used instead of the poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a number average degree of polymerization of 100. -Dimethoxyanthracene-9,10-diol ester) resin was prepared in the same manner as in Example 1 except that a resin was used.

EXAMPLE 12 Instead of a poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a number average degree of polymerization of 100, poly (undecandioic acid 2,6 having a number average degree of polymerization of 400 was used. -Dimethoxyanthracene-9,10-diol ester) resin was prepared in the same manner as in Example 1 except that a resin was used.

Comparative Example 5 Poly (undecandioic acid 2,6 having a number average degree of polymerization of 50) was used instead of the poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a number average degree of polymerization of 100. -Dimethoxyanthracene-9,10-diol ester) resin was prepared in the same manner as in Example 1 except that a resin was used.

Comparative Example 6 Poly (undecandioic acid 2,6 having a number average polymerization degree of 450 was used instead of the poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a number average polymerization degree of 100. -Dimethoxyanthracene-9,10-diol ester) was prepared in the same manner as in Example 1 except that a resin was used, but poly (undecandioic acid 2,6-dimethoxyanthracene-9,10-diol ester) was used. )
Sufficient concentration cannot be obtained due to poor solubility of the resin.
m could not be obtained.

The appearances of Examples 9 to 12 and Comparative Example 5 were compared. Table 3 shows the results.

[0041]

[Table 3]

As can be seen from Table 3, all of the examples have a good glossy appearance, but cracks occur in Comparative Example 5, and in Comparative Example 6, the predetermined film thickness is obtained as described above. Could not be obtained.

Example 13 Instead of a poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a number average degree of polymerization of 100, poly (dodecandioic acid 2,6 having a number average degree of polymerization of 100) was used. -Dimethoxyanthracene-9,10-diol ester) resin was prepared in the same manner as in Example 1 except that a resin was used.

Example 14 Instead of a poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a number average degree of polymerization of 100, poly (dodecandioic acid 2,6 having a number average degree of polymerization of 200) was used. -Dimethoxyanthracene-9,10-diol ester) resin was prepared in the same manner as in Example 1 except that a resin was used.

Example 15 Instead of a poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a number average degree of polymerization of 100, a poly (dodecandioic acid 2,6 having a number average degree of polymerization of 300) was used. -Dimethoxyanthracene-9,10-diol ester) resin was prepared in the same manner as in Example 1 except that a resin was used.

Example 16 Instead of poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a number average degree of polymerization of 100, poly (dodecandioic acid 2,6 having a number average degree of polymerization of 400 was used. -Dimethoxyanthracene-9,10-diol ester) resin was prepared in the same manner as in Example 1 except that a resin was used.

Comparative Example 7 Instead of a poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a number average degree of polymerization of 100, a poly (dodecandioic acid 2,6 having a number average degree of polymerization of 50) was used. -Dimethoxyanthracene-9,10-diol ester) resin was prepared in the same manner as in Example 1 except that a resin was used.

COMPARATIVE EXAMPLE 8 Instead of a poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a number average degree of polymerization of 100, a poly (dodecandioic acid 2,6 having a number average degree of polymerization of 450) was used. A photoreceptor was prepared in the same manner as in Example 1 except that a resin was used, but poly (2,6-dimethoxyanthracene-9,10-diol ester) was used. ) Sufficient concentration cannot be obtained due to poor solubility of the resin.
Could not be obtained.

Examples 13 to 16 created in this way
And Comparative Example 7 were compared in appearance. Table 4 shows the results.

[0050]

[Table 4]

Example 17 Instead of a poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a number average degree of polymerization of 100, a poly (tridecandioic acid 2,6 having a number average degree of polymerization of 100) was used. -Dimethoxyanthracene-9,10-diol ester) resin was prepared in the same manner as in Example 1 except that a resin was used.

Example 18 Instead of a poly (nonanediacid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a number average degree of polymerization of 100, a poly (tridecandioic acid 2,6 having a number average degree of polymerization of 200) was used. -Dimethoxyanthracene-9,10-diol ester) resin was prepared in the same manner as in Example 1 except that a resin was used.

Example 19 Instead of poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a number average degree of polymerization of 100, poly (tridecandioic acid 2,6 having a number average degree of polymerization of 300) was used. -Dimethoxyanthracene-9,10-diol ester) resin was prepared in the same manner as in Example 1 except that a resin was used.

Example 20 Instead of a poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a number average degree of polymerization of 100, a poly (tridecandioic acid 2,6 having a number average degree of polymerization of 400) was used. -Dimethoxyanthracene-9,10-diol ester) resin was prepared in the same manner as in Example 1 except that a resin was used.

COMPARATIVE EXAMPLE 9 Instead of poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a number average polymerization degree of 100, poly (tridecandioic acid 2,6 having a number average polymerization degree of 50) was used. -Dimethoxyanthracene-9,10-diol ester) resin was prepared in the same manner as in Example 1 except that a resin was used.

COMPARATIVE EXAMPLE 10 Instead of poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a number average degree of polymerization of 100, poly (tridecandioic acid 2,6 having a number average degree of polymerization of 450) was used. -Dimethoxyanthracene-9,10-diol ester) was tried in the same manner as in Example 1 except that a resin was used, but poly (tridecandioic acid 2,6-dimethoxyanthracene-9,10-diol ester) was used. )
Insufficient concentration of resin could be obtained due to poor solubility of resin.
Could not be obtained.

Examples 17 to 20 created in this way
And Comparative Example 9 were compared in appearance. Table 5 shows the results.

[0058]

[Table 5]

As can be seen from Table 5, all of the examples had a good glossy appearance, but cracks occurred in Comparative Example 9 and a predetermined film thickness was obtained in Comparative Example 10 as described above. Could not be obtained.

Example 21 Instead of poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a number average degree of polymerization of 100, poly (tetradecandioic acid 2,6 having a number average degree of polymerization of 100) was used. -Dimethoxyanthracene-9,10-diol ester) resin was prepared in the same manner as in Example 1 except that a resin was used.

Example 22 Instead of poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a number average degree of polymerization of 100, poly (tetradecandioic acid 2,6 having a number average degree of polymerization of 200) was used. -Dimethoxyanthracene-9,10-diol ester) resin was prepared in the same manner as in Example 1 except that a resin was used.

Example 23 Instead of a poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a number average degree of polymerization of 100, a poly (tetradecandioic acid 2,6 having a number average degree of polymerization of 300) was used. -Dimethoxyanthracene-9,10-diol ester) resin was prepared in the same manner as in Example 1 except that a resin was used.

Example 24 Instead of a poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a number average degree of polymerization of 100, a poly (tetradecandioic acid 2,6 having a number average degree of polymerization of 400) was used. -Dimethoxyanthracene-9,10-diol ester) resin was prepared in the same manner as in Example 1 except that a resin was used.

Comparative Example 11 Instead of a poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a number average degree of polymerization of 100, a poly (tetradecandioic acid 2,6 having a number average degree of polymerization of 50) was used. -Dimethoxyanthracene-9,10-diol ester) resin was prepared in the same manner as in Example 1 except that a resin was used.

COMPARATIVE EXAMPLE 12 Instead of a poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a number average degree of polymerization of 100, a poly (tetradecandioic acid 2,6 having a number average degree of polymerization of 450) was used. -Dimethoxyanthracene-9,10-diol ester) resin was used in the same manner as in Example 1 except that a resin was used, but poly (tetradecandioic acid 2,6) was used.
-Dimethoxyanthracene-9,10-diol ester) because of poor solubility of the resin, a sufficient concentration cannot be obtained.
A film thickness of 0 μm could not be obtained.

Examples 21 to 24 created as described above
And Comparative Example 11 were compared in appearance. Table 6 shows the results.

[0067]

[Table 6]

As can be seen from Table 6, each of the examples has a glossy and good appearance, but cracks occur in Comparative Example 11, and in Comparative Example 12, a predetermined film thickness is obtained as described above. Could not be obtained.

Example 25 Instead of a poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a number average degree of polymerization of 100, a poly (pentadecandioic acid 2,6 having a number average degree of polymerization of 100) was used. -Dimethoxyanthracene-9,10-diol ester) resin was prepared in the same manner as in Example 1 except that a resin was used.

Example 26 Instead of a poly (nonanediacid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a number average degree of polymerization of 100, poly (pentadecandioic acid 2,6 having a number average degree of polymerization of 200) was used. -Dimethoxyanthracene-9,10-diol ester) resin was prepared in the same manner as in Example 1 except that a resin was used.

Example 27 Instead of a poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a number average degree of polymerization of 100, a poly (pentadecandioic acid 2,6 having a number average degree of polymerization of 300) was used. -Dimethoxyanthracene-9,10-diol ester) resin was prepared in the same manner as in Example 1 except that a resin was used.

Example 28 Instead of a poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a number average degree of polymerization of 100, poly (pentadecandioic acid 2,6 having a number average degree of polymerization of 400 was used. -Dimethoxyanthracene-9,10-diol ester) resin was prepared in the same manner as in Example 1 except that a resin was used.

COMPARATIVE EXAMPLE 13 Instead of a poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a number average degree of polymerization of 100, poly (pentadecandioic acid 2,6 having a number average degree of polymerization of 50) was used. -Dimethoxyanthracene-9,10-diol ester) resin was prepared in the same manner as in Example 1 except that a resin was used.

COMPARATIVE EXAMPLE 14 Instead of a poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a number average degree of polymerization of 100, a poly (pentadecandioic acid 2,6 having a number average degree of polymerization of 450) was used. -Dimethoxyanthracene-9,10-diol ester) resin was used in the same manner as in Example 1 except that a resin was used, but poly (pentadecandioic acid 2,6) was used.
-Dimethoxyanthracene-9,10-diol ester) because of poor solubility of the resin, a sufficient concentration cannot be obtained.
A film thickness of 0 μm could not be obtained.

Examples 25 to 28 created in this way
And Comparative Example 13 were compared in appearance. Table 7 shows the results.

[0076]

[Table 7]

As can be seen from Table 7, all of the examples have a glossy and good appearance, but cracks occur in Comparative Example 13, and in Comparative Example 14, the predetermined film thickness is obtained as described above. Could not be obtained.

Example 29 Instead of a poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a weight average molecular weight to number average molecular weight ratio of 3, a poly (nonanediacid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a weight average molecular weight to number average molecular weight ratio of 4 was used. A photoconductor was prepared in the same manner as in Example 1, except that nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin was used.

Example 30 A poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a weight average molecular weight to number average molecular weight ratio of 3 was replaced with a poly (nonanediacid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a weight average molecular weight to number average molecular weight ratio of 5 A photoconductor was prepared in the same manner as in Example 1, except that nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin was used.

Comparative Example 15 Instead of the poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a weight average molecular weight to number average molecular weight ratio of 3, a poly (nonanediacid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a weight average molecular weight to number average molecular weight ratio of 2 was used. A photoconductor was prepared in the same manner as in Example 1, except that nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin was used.

Comparative Example 16 Instead of a poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a weight average molecular weight to number average molecular weight ratio of 3, a poly (nonanediacid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a weight average molecular weight to number average molecular weight ratio of 6 was used. A photoconductor was prepared in the same manner as in Example 1, except that nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin was used.

The appearance and electrophotographic characteristics of Examples 1, 29 and 30 and Comparative Examples 15 and 16 prepared as described above were compared. The electrophotographic characteristics are based on the electrostatic recording paper tester "SP-
428 "(manufactured by Kawaguchi Electric Co., Ltd.) at room temperature. The photoreceptor was subjected to a corona discharge of -6.0 kV for 10 seconds in a dark place to negatively charge the surface of the photoreceptor, to measure the charged potential Vo (V), and then kept in a dark place for 2 seconds with the corona discharge stopped. Then, the surface of the photoreceptor is irradiated with laser light having a wavelength of 780 nm at 1 μJ / cm ² , and this light is irradiated for 10 minutes.
The residual potential Vr (V) when the surface of the photoconductor was irradiated for 2 seconds was measured. Table 8 shows the results.

[0083]

[Table 8]

As can be seen from Table 8, all of the examples had good glossy appearance, but in Comparative Example 15, cracks occurred. In each of the examples, good electrical characteristics were obtained, but in Comparative Example 16, the absolute value of Vr was high.

Example 31 A poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a weight average molecular weight to number average molecular weight ratio of 3 was replaced with a poly (nonanedioic acid 2,6 dimethoxyanthracene-9,10-diol ester) resin having a weight average molecular weight to number average molecular weight ratio of 3. A photoreceptor was prepared in the same manner as in Example 1, except that a decandioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin was used.

Example 32 Instead of poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a weight average molecular weight to number average molecular weight ratio of 3, poly (nonanediacid 2,6-dimethoxyanthracene-9,10-diol ester) having a weight average molecular weight to number average molecular weight ratio of 4 was used. A photoreceptor was prepared in the same manner as in Example 1, except that a decandioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin was used.

Example 33 Instead of poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a weight average molecular weight to number average molecular weight ratio of 3, poly (nonanediacid 2,6-dimethoxyanthracene-9,10-diol ester) having a weight average molecular weight to number average molecular weight ratio of 5 was used. A photoreceptor was prepared in the same manner as in Example 1, except that a decandioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin was used.

Comparative Example 17 Instead of the poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a weight average molecular weight to number average molecular weight ratio of 3, a poly (nonanediacid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a weight average molecular weight to number average molecular weight ratio of 2 was used. A photoreceptor was prepared in the same manner as in Example 1, except that a decandioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin was used.

Comparative Example 18 Instead of a poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a weight average molecular weight to number average molecular weight ratio of 3, a poly (nonanediacid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a weight average molecular weight to number average molecular weight ratio of 6 was used. A photoreceptor was prepared in the same manner as in Example 1, except that a decandioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin was used.

Examples 31 to 33 created in this way
The appearance and electrophotographic properties of Comparative Examples 17 and 18 were compared in the same manner as in Table 1. Table 9 shows the results.

[0091]

[Table 9]

As can be seen from Table 9, all of the examples had a glossy and good appearance. In Comparative Example 17, cracks occurred. In each of the examples, good electrical characteristics were obtained, but in Comparative Example 18, the absolute value of Vr was high.

Example 34 Instead of the poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a weight average molecular weight to number average molecular weight ratio of 3, a poly (nonanediacid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a weight average molecular weight to number average molecular weight ratio of 3 was used. A photoconductor was prepared in the same manner as in Example 1, except that undecandioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin was used.

Example 35 A poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a weight average molecular weight to number average molecular weight ratio of 3 was replaced with a poly (nonanediacid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a weight average molecular weight to number average molecular weight ratio of 4 A photoconductor was prepared in the same manner as in Example 1, except that undecandioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin was used.

Example 36 Instead of a poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a weight average molecular weight to number average molecular weight ratio of 3, poly (nonanediacid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a weight average molecular weight to number average molecular weight ratio of 5 was used. A photoconductor was prepared in the same manner as in Example 1, except that undecandioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin was used.

Comparative Example 19 Instead of a poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a weight average molecular weight to number average molecular weight ratio of 3, a poly (nonanediacid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a weight average molecular weight to number average molecular weight ratio of 2 was used. A photoconductor was prepared in the same manner as in Example 1, except that undecandioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin was used.

Comparative Example 20 Instead of a poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a weight average molecular weight to number average molecular weight ratio of 3, poly (nonanediacid 2,6-dimethoxyanthracene-9,10-diol ester) having a weight average molecular weight to number average molecular weight ratio of 6 was used. A photoconductor was prepared in the same manner as in Example 1, except that undecandioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin was used.

Examples 34 to 36 created in this way
The appearance and electrophotographic characteristics of Comparative Examples 19 and 20 were compared in the same manner as in Table 1. Table 10 shows the results.

[0099]

[Table 10]

As can be seen from Table 10, all of the examples had good glossy appearance, but in Comparative Example 19, cracks occurred. In each of the examples, good electrical characteristics were obtained, but in Comparative Example 20, the absolute value of Vr was high.

Example 37 Instead of a poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a weight average molecular weight to number average molecular weight ratio of 3, a poly (nonanediacid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a weight average molecular weight to number average molecular weight ratio of 3 was used. A photoconductor was prepared in the same manner as in Example 1, except that dodecanediacid 2,6-dimethoxyanthracene-9,10-diol ester) resin was used.

Example 38 Instead of a poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a weight average molecular weight to number average molecular weight ratio of 3, a poly (nonanediacid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a weight average molecular weight to number average molecular weight ratio of 4 was used. A photoconductor was prepared in the same manner as in Example 1, except that dodecanediacid 2,6-dimethoxyanthracene-9,10-diol ester) resin was used.

Example 39 In place of the poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a weight average molecular weight to number average molecular weight ratio of 3, a poly (nonanediacid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a weight average molecular weight to number average molecular weight ratio of 5 was used. A photoconductor was prepared in the same manner as in Example 1, except that dodecanediacid 2,6-dimethoxyanthracene-9,10-diol ester) resin was used.

COMPARATIVE EXAMPLE 21 Instead of a poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a weight average molecular weight to number average molecular weight ratio of 3, a poly (nonanediacid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a weight average molecular weight to number average molecular weight ratio of 2 was used. A photoconductor was prepared in the same manner as in Example 1, except that dodecanediacid 2,6-dimethoxyanthracene-9,10-diol ester) resin was used.

Comparative Example 22 Instead of a poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a weight average molecular weight to number average molecular weight ratio of 3, a poly (nonanediacid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a weight average molecular weight to number average molecular weight ratio of 6 was used. A photoconductor was prepared in the same manner as in Example 1, except that dodecanediacid 2,6-dimethoxyanthracene-9,10-diol ester) resin was used.

Embodiments 37 to 39 created in this way
The appearance and electrophotographic characteristics of Comparative Examples 21 and 22 were compared in the same manner as in Table 8. Table 11 shows the results.

[0107]

[Table 11]

As can be seen from Table 11, all of the examples had a good glossy appearance, but in Comparative Example 21, cracks occurred. In each of the examples, good electrical characteristics were obtained, but in Comparative Example 22, the absolute value of Vr was high.

Example 40 In place of the poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a weight average molecular weight to number average molecular weight ratio of 3, a poly (nonanediacid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a weight average molecular weight to number average molecular weight ratio of 3 was used. A photoconductor was prepared in the same manner as in Example 1, except that 2,6-dimethoxyanthracene-9,10-diol tridecandioate) resin was used.

Example 41 Instead of a poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a weight average molecular weight to number average molecular weight ratio of 3, a poly (nonanediacid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a weight average molecular weight to number average molecular weight ratio of 4 was used. A photoconductor was prepared in the same manner as in Example 1, except that 2,6-dimethoxyanthracene-9,10-diol tridecandioate) resin was used.

Example 42 A poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a weight average molecular weight to number average molecular weight ratio of 3 was replaced by a poly (nonanediacid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a weight average molecular weight to number average molecular weight ratio of 5 A photoconductor was prepared in the same manner as in Example 1, except that 2,6-dimethoxyanthracene-9,10-diol tridecandioate) resin was used.

Comparative Example 23 Instead of a poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a weight average molecular weight to number average molecular weight ratio of 3, a poly (nonanediacid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a weight average molecular weight to number average molecular weight ratio of 2 was used. A photoconductor was prepared in the same manner as in Example 1, except that 2,6-dimethoxyanthracene-9,10-diol tridecandioate) resin was used.

Comparative Example 24 Instead of the poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a weight average molecular weight to number average molecular weight ratio of 3, a poly (nonanediacid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a weight average molecular weight to number average molecular weight ratio of 6 was used. A photoconductor was prepared in the same manner as in Example 1, except that 2,6-dimethoxyanthracene-9,10-diol tridecandioate) resin was used.

Embodiments 40 to 42 created in this way
The appearance and electrophotographic characteristics of Comparative Examples 23 and 24 were compared in the same manner as in Table 8. Table 12 shows the results.

[0115]

[Table 12]

As can be seen from Table 12, all of the Examples had good glossy appearance, but Comparative Example 23 had cracks. In each of the examples, the electrical characteristics were good, but in Comparative Example 24, the absolute value of Vr was high.

Example 43 In place of the poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a weight average molecular weight to number average molecular weight ratio of 3, poly (nonanediacid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a weight average molecular weight to number average molecular weight ratio of 3 was used. A photoconductor was prepared in the same manner as in Example 1, except that 2,6-dimethoxyanthracene-9,10-diol ester (tetradecandioic acid) resin was used.

Example 44 Instead of a poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a weight average molecular weight to number average molecular weight ratio of 3, a poly (nonanediacid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a weight average molecular weight to number average molecular weight ratio of 4 was prepared. A photoconductor was prepared in the same manner as in Example 1, except that 2,6-dimethoxyanthracene-9,10-diol ester (tetradecandioic acid) resin was used.

Example 45 In place of the poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a weight average molecular weight to number average molecular weight ratio of 3, a poly (nonanediacid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a weight average molecular weight to number average molecular weight ratio of 5 was used. A photoconductor was prepared in the same manner as in Example 1, except that 2,6-dimethoxyanthracene-9,10-diol ester (tetradecandioic acid) resin was used.

Comparative Example 25 Instead of a poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a weight average molecular weight to number average molecular weight ratio of 3, poly (nonanediacid 2,6-dimethoxyanthracene-9,10-diol ester) having a weight average molecular weight to number average molecular weight ratio of 2 was used. A photoconductor was prepared in the same manner as in Example 1, except that 2,6-dimethoxyanthracene-9,10-diol ester (tetradecandioic acid) resin was used.

Comparative Example 26 Instead of a poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a weight average molecular weight to number average molecular weight ratio of 3, a poly (nonanediacid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a weight average molecular weight to number average molecular weight ratio of 6 was used. A photoconductor was prepared in the same manner as in Example 1, except that 2,6-dimethoxyanthracene-9,10-diol ester (tetradecandioic acid) resin was used.

Embodiments 43 to 45 created in this way
The appearance and electrophotographic properties of Comparative Examples 25 and 26 were compared in the same manner as in Table 8. Table 13 shows the results.

[0123]

[Table 13]

As can be seen from Table 13, all of the examples had a good glossy appearance, but in Comparative Example 25, cracks occurred. In each of the examples, good electrical characteristics were obtained, but in Comparative Example 26, the absolute value of Vr was high.

Example 46 Instead of a poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a weight average molecular weight to number average molecular weight ratio of 3, a poly (nonanediacid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a weight average molecular weight to number average molecular weight ratio of 3 was used. A photoconductor was prepared in the same manner as in Example 1, except that pentadecandioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin was used.

Example 47 Instead of a poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a weight average molecular weight to number average molecular weight ratio of 3, a poly (nonanediacid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a weight average molecular weight to number average molecular weight ratio of 4 was used. A photoconductor was prepared in the same manner as in Example 1, except that pentadecandioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin was used.

Example 48 Instead of a poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a weight average molecular weight to number average molecular weight ratio of 3, a poly (nonanediacid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a weight average molecular weight to number average molecular weight ratio of 5 was used. A photoconductor was prepared in the same manner as in Example 1, except that pentadecandioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin was used.

Comparative Example 27 Instead of the poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a weight average molecular weight to number average molecular weight ratio of 3, a poly (nonanediacid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a weight average molecular weight to number average molecular weight ratio of 2 was used. A photoconductor was prepared in the same manner as in Example 1, except that pentadecandioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin was used.

Comparative Example 28 Instead of a poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a weight average molecular weight to number average molecular weight ratio of 3, a poly (nonanediacid 2,6-dimethoxyanthracene-9,10-diol ester) resin having a weight average molecular weight to number average molecular weight ratio of 6 was used. A photoconductor was prepared in the same manner as in Example 1, except that pentadecandioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin was used.

Embodiments 46 to 48 created in this way
The appearance and electrophotographic characteristics of Comparative Examples 27 and 28 were compared in the same manner as in Table 8. Table 14 shows the results.

[0131]

[Table 14]

As can be seen from Table 14, all of the examples had good glossy appearance, but in Comparative Example 27, cracks occurred. In each of the examples, the electrical characteristics were good, but in Comparative Example 28, the absolute value of Vr was high.

Example 49 Poly (nonanedioic acid 2,6-dimethoxyanthracene)
Instead of 9,10-diol ester) resin, poly (2,6-dimethoxyanthracene-9,1 decandioate) is used.
A photoconductor was prepared in the same manner as in Example 1, except that a (0-diol ester) resin was used.

Example 50 Poly (nonanedioic acid 2,6-dimethoxyanthracene)
Instead of 9,10-diol ester) resin, poly (undecandioic acid 2,6-dimethoxyanthracene)
A photoreceptor was prepared in the same manner as in Example 1 except that (9,10-diol ester) resin was used.

Example 51 Poly (nonanedioic acid 2,6-dimethoxyanthracene)
Instead of 9,10-diol ester resin, poly (2,6-dimethoxyanthracene-9,
Example 1 except that a 10-diol ester) resin was used.
A photoreceptor was prepared in the same manner as described above.

Example 52 Poly (nonanedioic acid 2,6-dimethoxyanthracene)
Instead of 9,10-diol ester) resin, poly (2,6-dimethoxyanthracene tridecanedioate)
A photoreceptor was prepared in the same manner as in Example 1 except that (9,10-diol ester) resin was used.

Example 53 Poly (nonanedioic acid 2,6-dimethoxyanthracene)
Instead of 9,10-diol ester) resin, poly (2,6-dimethoxyanthracene tetradecandioate)
A photoreceptor was prepared in the same manner as in Example 1 except that (9,10-diol ester) resin was used.

Example 54 Poly (nonanedioic acid 2,6-dimethoxyanthracene)
Instead of 9,10-diol ester) resin, poly (pentadecandioic acid 2,6-dimethoxyanthracene-
A photoreceptor was prepared in the same manner as in Example 1 except that (9,10-diol ester) resin was used.

Comparative Example 29 A charge generation layer was formed in the same manner as in Example 1. On the charge generation layer thus obtained, 1-phenyl-3- (p-diethylaminostyryl) -5- (p
-Diethylaminophenyl) -2-pyrazolin (ASP
P) 10 parts by weight, polycarbonate resin (Panlite C)
-1400: manufactured by Teijin Chemicals Ltd.) A coating solution consisting of 10 parts by weight of dichloromethane and 280 parts by weight of dichloromethane was applied by a wire bar, and a charge transport layer having a thickness of 20 μm after drying was formed to prepare a photoconductor. The electrophotographic characteristics of the thus-prepared Examples 1 and 49 to 54 and Comparative Example 29 were measured in the same manner as in Table 8. Table 15 shows the results.

[0140]

[Table 15]

As can be seen from Table 15, all of the examples and comparative examples exhibited good characteristics in which the charge potential was high and the light portion potential was low. Next, these samples were subjected to IsoparL (EXXON C), which is one of the components of a liquid developing type developer.
(HEMICAL JAPAN) for 24 hours, and then dried. The appearance was observed and the electrophotographic characteristics were measured in the same manner as in Table 8. Table 16 shows the results.

[0142]

[Table 16]

As can be seen from Table 16, the examples were all good without any change in appearance and retaining the electrophotographic properties before immersion, but the comparative examples had cracks.

The same samples as in Examples 1 and 49 to 54 and Comparative Example 29 were newly prepared, and Examples 55 to 61 were prepared.
Table 17 shows the results of measuring the electrophotographic characteristics of Comparative Example 30 in the same manner as in Table 8.

[0145]

[Table 17]

As can be seen from Table 17, both Examples and Comparative Examples had good characteristics with a high potential and a low bright portion potential.

Next, these samples were immersed in methyl ethyl ketone (manufactured by Wako Pure Chemical Industries, Ltd.), which is one of the components of a liquid developing type developer, for 24 hours, dried, and observed for appearance and in the same manner as in Table 8. Photographic properties were measured. Table 18 shows the results.
Shown in

[0148]

[Table 18]

As can be seen from Table 18, the examples were all good without any change in appearance and retaining the electrophotographic properties before immersion, but the comparative examples were whitened.

Example 62 A charge generation layer was formed in the same manner as in Example 1. On the thus-obtained charge generating layer, a coating liquid composed of 15 parts by weight of poly (methylphenylsilane), which is a polymer charge transporting agent, and 85 parts by weight of toluene was applied as a charge transporting layer using a wire bar. A charge transport layer having a thickness of 15 μm after drying was formed. On the thus obtained charge transport layer, a poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin 10 was further provided as a charge transport layer.
A coating liquid consisting of 290 parts by weight of tetrachloroethylene was applied by a wire bar, and a charge transport layer having a thickness of 5 μm after drying was formed to prepare a photoreceptor. Here, poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-
The ratio of the weight average molecular weight to the number average molecular weight of the diol ester) resin is 3, and the number average polymerization degree n is 100. Hereinafter, the same molecular weight ratio and n are used until reaching Example 75.

Example 63 Poly (nonanedioic acid 2,6-dimethoxyanthracene)
Instead of 9,10-diol ester) resin, poly (2,6-dimethoxyanthracene-9,1 decandioate) is used.
Example 62 except that a (0-diol ester) resin was used.
A photoreceptor was prepared in the same manner as described above.

Example 64 Poly (nonanedioic acid 2,6-dimethoxyanthracene)
Instead of 9,10-diol ester) resin, poly (undecandioic acid 2,6-dimethoxyanthracene)
A photoconductor was prepared in the same manner as in Example 62, except that (9,10-diol ester) resin was used.

Example 65 Poly (nonanedioic acid 2,6-dimethoxyanthracene)
Instead of 9,10-diol ester resin, poly (2,6-dimethoxyanthracene-9,
Example 6 except that a 10-diol ester) resin was used.
A photoconductor was prepared in the same manner as in No. 2.

Example 66 Poly (nonanedioic acid 2,6-dimethoxyanthracene)
Instead of 9,10-diol ester) resin, poly (2,6-dimethoxyanthracene tridecanedioate)
A photoconductor was prepared in the same manner as in Example 62, except that (9,10-diol ester) resin was used.

Example 67 Poly (nonanedioic acid 2,6-dimethoxyanthracene)
Instead of 9,10-diol ester) resin, poly (2,6-dimethoxyanthracene tetradecandioate)
A photoconductor was prepared in the same manner as in Example 62, except that (9,10-diol ester) resin was used.

Example 68 Poly (2,6-dimethoxyanthracene nonanedioate)
Instead of 9,10-diol ester) resin, poly (pentadecandioic acid 2,6-dimethoxyanthracene-
A photoconductor was prepared in the same manner as in Example 62, except that (9,10-diol ester) resin was used.

Comparative Example 31 A charge generation layer was formed in the same manner as in Example 1. On the thus-obtained charge generating layer, a coating liquid composed of 15 parts by weight of poly (methylphenylsilane), which is a polymer charge transporting agent, and 85 parts by weight of toluene was applied as a charge transporting layer using a wire bar. A charge transporting layer having a thickness of 20 μm after drying was formed to prepare a photoreceptor.

The electrophotographic characteristics of Examples 62 to 68 and Comparative Example 31 were measured in the same manner as in Table 8. The results are shown in Table 19.

[0159]

[Table 19]

As can be seen from Table 19, in both of the examples and comparative examples, the charge potential was high, the bright portion potential was low, and good characteristics were obtained. Next, these samples were subjected to IsoparL (EXXON C), which is one of the components of a liquid developing type developer.
(HEMICAL JAPAN) for 24 hours, dried, observed for appearance, and measured for electrophotographic properties in the same manner as in Table 8. The results are shown in Table 20.

[0161]

[Table 20]

As can be seen from Table 20, the examples were all good without any change in appearance and retaining the electrophotographic properties before immersion, but the comparative examples had cracks.

Example 69 A charge generation layer was formed in the same manner as in Example 1. On the charge generation layer thus obtained, 1-phenyl-3- (p-diethylaminostyryl) -5- (p
-Diethylaminophenyl) -2-pyrazolin (ASP
P) 10 parts by weight, polycarbonate resin (Panlite C)
-1400: manufactured by Teijin Chemicals Ltd.) A coating solution consisting of 10 parts by weight and 280 parts by weight of dichloromethane was applied using a wire bar to form a charge transport layer having a thickness of 15 μm after drying.
A coating liquid comprising 10 parts by weight of a poly (nonanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin and 290 parts by weight of tetrachloroethylene as a charge transporting layer on the charge transporting layer thus obtained. Was applied with a wire bar, and a charge transport layer having a thickness of 5 μm after drying was formed to prepare a photoreceptor.

Example 70 Poly (nonanedioic acid 2,6-dimethoxyanthracene)
Instead of 9,10-diol ester) resin, poly (2,6-dimethoxyanthracene-9,1 decandioate) is used.
Example 69 except that a (0-diol ester) resin was used.
A photoreceptor was prepared in the same manner as described above.

Example 71 Poly (nonanedioic acid 2,6-dimethoxyanthracene)
Instead of 9,10-diol ester) resin, poly (undecandioic acid 2,6-dimethoxyanthracene)
A photoconductor was prepared in the same manner as in Example 69 except that a (9,10-diol ester) resin was used.

Example 72 Poly (nonanedioic acid 2,6-dimethoxyanthracene)
Instead of 9,10-diol ester resin, poly (2,6-dimethoxyanthracene-9,
Example 6 except that a 10-diol ester) resin was used.
A photoconductor was prepared in the same manner as in No. 9.

Example 73 Poly (nonanedioic acid 2,6-dimethoxyanthracene)
Instead of 9,10-diol ester) resin, poly (2,6-dimethoxyanthracene tridecanedioate)
A photoconductor was prepared in the same manner as in Example 69 except that a (9,10-diol ester) resin was used.

Example 74 Poly (nonanedioic acid 2,6-dimethoxyanthracene)
Instead of 9,10-diol ester) resin, poly (2,6-dimethoxyanthracene tetradecandioate)
A photoconductor was prepared in the same manner as in Example 69 except that a (9,10-diol ester) resin was used.

Example 75 Poly (nonanedioic acid 2,6-dimethoxyanthracene)
Instead of 9,10-diol ester) resin, poly (pentadecandioic acid 2,6-dimethoxyanthracene-
A photoconductor was prepared in the same manner as in Example 69 except that a (9,10-diol ester) resin was used.

The electrophotographic characteristics of Examples 69 to 75 and Comparative Example 29 were measured in the same manner as in Table 8. The results are shown in Table 21.

[0171]

[Table 21]

As can be seen from Table 21, all of the examples had good characteristics in which the charge potential was high and the light portion potential was low. Next, the samples of Examples 69 to 75 and Comparative Example 29 were subjected to Isop, which is one of the components of a liquid developing system developer.
ar L (EXXON CHEMICAL JAPAN
Immersion for 24 hours, dried, and observed for appearance and measured for electrophotographic properties in the same manner as in Table 8. Table 22 shows the results.
Shown in

[0173]

[Table 22]

As can be seen from Table 22, in each of the examples, there was no change in appearance and the electrophotographic properties before immersion were maintained, and the results were good.

[0175]

According to the present invention, a charge generation layer and a charge transport layer are provided on a conductive substrate, the charge generation layer is a layer containing a charge generation substance, and the charge transport layer is represented by the chemical formula (I). The organic photoconductive layer is excellent in solvent resistance because of containing the indicated poly (alkane diacid 2,6-dimethoxyanthracene-9,10-diol ester) resin, and has excellent reliability in liquid developing method for liquid developing electrophotography. A photoreceptor is obtained.

[Brief description of the drawings]

FIG. 1 is a sectional view showing an electrophotographic photosensitive member for liquid development according to an embodiment of the present invention.

FIG. 2 is a sectional view showing an electrophotographic photosensitive member for liquid development according to another embodiment of the present invention.

FIG. 3 is a sectional view showing an electrophotographic photosensitive member for liquid development according to still another embodiment of the present invention.

[Explanation of symbols]

 REFERENCE SIGNS LIST 1 conductive substrate 2 organic photoconductive layer 3 charge generation layer 4 charge transport layer 5 charge transport layer 6 charge transport layer 7 charge transport layer

Claims (7)

(57) [Claims] A charge generating layer and a charge transporting layer are provided on a conductive substrate, wherein the charge generating layer is a layer containing a charge generating substance, and the charge transporting layer is a poly (alkanediamine) represented by the chemical formula (I). An electrophotographic photoreceptor for liquid development, comprising an (acid 2,6-dimethoxyanthracene-9,10-diol ester) resin. Embedded image (Here, m is an integer of 1 or more, n is 100 to 400, and the ratio of the weight average molecular weight to the number average molecular weight is 3 to 5.) 2. The electrophotographic photosensitive member for liquid development according to claim 1, wherein the charge transport layer is the outermost layer. 3. The electrophotographic photoconductor for liquid development according to claim 1, wherein the charge transport layer comprises a plurality of layers. 4. The electrophotographic photoreceptor for liquid development according to claim 3, wherein the outermost layer of the charge transporting layer is a poly (alkane diacid 2,6-dimethoxyanthracene-9,10-diol) represented by the formula (I). An electrophotographic photoreceptor for liquid development, comprising an ester) resin. 5. The electrophotographic photosensitive member for liquid development according to claim 3, wherein the inner layer of the charge transport layer contains a polymer charge transport material. 6. An electrophotographic photoconductor for liquid development according to claim 3, wherein the inner layer of the charge transport layer contains a low molecular charge transport material. 7. The electrophotographic photoreceptor for liquid development according to claim 1, wherein m of the poly (alkanedioic acid 2,6-dimethoxyanthracene-9,10-diol ester) resin represented by the chemical formula (I) is 7 13. An electrophotographic photosensitive member for liquid development, wherein