JP2007161619A - Method for production of organic compound, electronic material obtained by the same and electronic device, electrophotographic photoreceptor, and image forming device using the same - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a method for production of an organic compound of high purity in high yield by using a carbonate. <P>SOLUTION: In the method for production of an organic compound by allowing raw materials to react with each other, a carbonate having a number average particle size of 5 to 60 μm is allowed to exist in the reaction system of the reaction. <P>COPYRIGHT: (C)2007,JPO&INPIT

Description

  The present invention relates to a method for producing an organic compound, an electronic material obtained by the production method, and an electronic device, an electrophotographic photoreceptor, and an image forming apparatus using the same.

  In general, the characteristics of an electronic device are greatly influenced not only by the electronic material used but also by the manufacturing method thereof. In particular, when an organic compound is used for the electronic material, the effect is remarkable. In particular, it is known that the influence of the manufacturing method of the electronic material to be used appears strongly with respect to the electrical characteristics, stability, and durability of the electronic device. There is a point that cannot be explained only by the purity of the electronic material and the impurities in the electronic material, and an effective manufacturing method is always required for electrical characteristics.

  As one method for producing an organic compound, a method using a carbonate is known. Carbonate is a base produced from carbon dioxide, which is one of the causes of the greenhouse effect. Therefore, carbonate is a compound with a small environmental load. However, the use of carbonate is relatively limited because its reactivity and solubility in organic solvents are not sufficiently high.

For example, as a method for synthesizing an organic compound using a carbonate, a classic method represented by the Ullmann reaction is known. However, in the Ullmann reaction and the like, it is known that the product may be colored from the viewpoint of reaction rate and reaction temperature.
Further, as another example of a method for synthesizing an organic compound using a carbonate, an ether production reaction is known. In the ether formation reaction, generally, a base stronger than potassium carbonate (metal hydroxide or the like) is generally used, as represented by the Williamson reaction. However, in this case, the use of carbonate is generally used for limited use of activated sites and the like.

In addition, many examples of using carbonates in polymer synthesis and the like are known. However, it has been difficult to synthesize a polymer having a large molecular weight even if carbonate is used in polymer synthesis.
Furthermore, many alkylation reactions by using potassium carbonate and an alkylating agent in combination as a base are also known. However, such an alkyl reaction is difficult to obtain a sufficient yield and purity.

Patent Document 1 reports an example in which powdered potassium carbonate is used when alkylating imidazole. Among them, there is an example using potassium carbonate having a particle size of around 74 μm, but finer potassium carbonate has been reported to decrease the yield.
Furthermore, Patent Document 2 reports that it is preferable to use powdery potassium carbonate of 200 μm or less in the reaction between a halogen compound and an active methylene compound. However, Patent Document 2 does not show a specific example, and its effect is unknown.
In addition, an example using pulverized potassium carbonate having an average particle diameter of 60 μm or less or 50 μm or less has not been reported.

JP-A-11-171869 Japanese Patent Laid-Open No. 11-116506

  The present invention has been made in view of the above circumstances, and an object thereof is to enable an organic compound to be produced with high yield and high purity in an organic compound production method using a carbonate. It is another object of the present invention to provide an electronic material manufactured using the manufacturing method, an electronic device, an electrophotographic photosensitive member, and an image forming apparatus using the electronic material.

As a result of intensive studies to solve the above-mentioned problems, the present inventors can produce an organic compound with good yield and industrially advantageous by using a carbonate having a number average particle diameter of 60 μm or less and 5 μm or more. As a result, they have found the present invention.
That is, the gist of the present invention is a method for producing an organic compound in which a raw material is reacted to produce an organic compound, and a carbonate having a number average particle size of 60 μm or less and 5 μm or more is present in the reaction system of the reaction. It exists in the manufacturing method of the organic compound characterized by the above-mentioned (Claim 1).

At this time, the carbonate is preferably a potassium salt.
Moreover, as said organic compound, it is preferable to manufacture at least 1 sort (s) chosen from the group which consists of an amine compound, an aryl compound, an ether compound, an alkene compound, and an ester compound (Claim 3).
Furthermore, it is preferable that the carbonate has a specific surface area of 0.5 m ² / g or more.

The bulk density of the carbonate is preferably 0.25 g / mL or more and 1.1 g / mL or less (Claim 5).
Furthermore, the reaction temperature of the reaction is preferably −10 ° C. or more and 250 ° C. or less (Claim 6).
In the reaction, it is preferable to use a reaction solvent having a relative dielectric constant of 2 or more and 50 or less (Claim 7).

Another gist of the present invention resides in an electronic material produced by the method for producing an organic compound (claim 8).
Still another subject matter of the present invention lies in an electronic device using the above-mentioned electronic material (claim 9).
Still another subject matter of the present invention is an electrophotographic photosensitive member having a photosensitive layer on a conductive support, the electrophotographic photosensitive member comprising the above-described electronic material in the photosensitive layer. (Claim 10).

  Still another gist of the present invention includes the electrophotographic photosensitive member, a charging unit that charges the electrophotographic photosensitive member, an exposure unit that exposes the charged electrophotographic photosensitive member to form an electrostatic latent image, and An image forming apparatus comprising: a developing unit that develops an electrostatic latent image formed on the electrophotographic photosensitive member (claim 11).

  Still another gist of the present invention includes the electrophotographic photosensitive member, a charging unit that charges the electrophotographic photosensitive member, an exposure unit that exposes the charged electrophotographic photosensitive member to form an electrostatic latent image, and The electrophotographic photosensitive member cartridge includes at least one developing unit that develops the electrostatic latent image formed on the electrophotographic photosensitive member.

According to the method for producing an organic compound of the present invention, it is possible to produce an organic compound with high yield and high purity using a carbonate.
The electronic material of the present invention produced by the method for producing an organic compound of the present invention can exhibit high performance when used in an electronic device, an electrophotographic photoreceptor and an image forming apparatus.
Furthermore, the electronic device, electrophotographic photosensitive member, and image forming apparatus of the present invention can exhibit high performance.

  DESCRIPTION OF EMBODIMENTS Hereinafter, embodiments of the present invention will be described in detail. However, the present invention is not limited to the examples and the like described below, and may be arbitrarily modified without departing from the gist of the present invention. Is possible.

[I. Method for producing organic compound]
The method for producing an organic compound of the present invention (hereinafter, appropriately referred to as “the method of production of the present invention”) is a method for producing an organic compound in which an organic compound is produced by reacting a raw material. In the production method of the present invention, a carbonate having a number average particle size of 60 μm or less and 5 μm or more is present in the reaction system of the reaction.

[Carbonate]
The carbonate is present as a reaction accelerator in the reaction system in the production method of the present invention.
The kind of carbonate concerning this invention is arbitrary unless the effect of this invention is impaired remarkably. Accordingly, the carbonate may be any of a normal salt, a hydrogen salt (hydrogen carbonate) and a hydroxide salt, but a normal salt is preferably used.

Examples of preferred carbonates that can enhance the effects of the present invention include alkali metal salts and alkaline earth metal salts. Among these, alkali metal salts are preferable, and potassium carbonate (potassium salt) is particularly preferable.
In addition, carbonate may be used individually by 1 type and may use 2 or more types together by arbitrary combinations and a ratio.

The carbonate according to the present invention is used in the form of particles having a predetermined number average particle diameter. Specifically, the number average particle diameter of the carbonate is usually 60 μm or less, preferably 50 μm or less, more preferably 30 μm or less, and usually 5 μm or more. By setting the number average particle diameter of the carbonate within the above range, it is possible to produce an organic compound with high yield and high purity. In addition, from the viewpoint of the stability of the carbonate particles, it is preferably 10 μm or more.
The number average particle diameter can be measured by an existing method, and a microscope, SEM (scanning electron microscope), laser scattering method, or the like is selected as a measuring means. Measured by a laser scattering method to confirm that the number average particle diameter of the carbonate falls within the above range.

Moreover, the carbonate according to the present invention is not limited in specific surface area unless the effects of the present invention are significantly impaired. However, usually, the specific surface area of the carbonate, usually 0.5 m ² / g or more, preferably 0.6 m ² / g or more, more preferably 0.8 m ² / g or more, more preferably 1.0 m ² / g or more, particularly preferably 1.3 m ² / g or more. In particular, in the case of a carbonate having a number average particle size of 40 μm or more and 60 μm or less, the specific surface area of the carbonate is preferably 1.7 m ² / g or more. By setting the specific surface area of the carbonate within this range, an advantage of increasing the reactivity can be obtained.

On the other hand, if the specific surface area of the carbonate is too large, it is easy to absorb moisture, which is inconvenient to handle and may deteriorate the storage stability. Therefore, the specific surface area of the carbonate of the present invention is preferably from 2.5 m ² / g or less, more preferably 2.0 m ² / g, more preferably not more than 1.9m ² / g.

  In addition, the BET method etc. are used for the measurement of the specific surface area of carbonate. The BET method is a method in which molecules having a known adsorption occupation area are adsorbed on the surface of powder particles at the temperature of liquid nitrogen, and the specific surface area of the sample is obtained from the amount. The BET method by low-temperature low-humidity physical adsorption of an inert gas is most often used, and a method using nitrogen is simple and preferable. Here, the specific surface area is measured by the BET method using nitrogen.

  Further, the carbonate according to the present invention is not limited in its bulk density unless the effects of the present invention are significantly impaired. However, when a reaction solvent is used in the reaction, depending on the reaction solvent, if the specific gravity of the carbonate is heavier than the specific gravity of the reaction solvent, it may not be possible to perform stirring well. Therefore, it is desirable that the bulk density of the carbonate is lower than that of the reaction solvent. Specifically, the bulk density of the carbonate is usually 1.1 g / mL or less, preferably 1.0 g / mL or less, more preferably 0.9 g / mL or less.

On the other hand, if the bulk density of the carbonate is too light, the powder cake may float and stirring may not be performed satisfactorily. Therefore, the bulk density of the carbonate is usually 0.25 g / mL or more, preferably 0.8. 30 g / mL or more, more preferably 0.40 g / mL or more.
The bulk density can be measured by a method according to JIS K 6891.

  Moreover, there is no restriction | limiting in the usage-amount of the carbonate concerning this invention, and it is arbitrary unless the effect of this invention is impaired remarkably. For example, when the reaction is performed in a liquid phase reaction system by using a reaction solvent, the carbonate concentration in the reaction system is usually 0.1 g / mL or more, preferably 0.2 g / mL. mL or more, more preferably 0.3 g / mL or more, and usually 2 g / mL or less, preferably 1 g / mL or less, more preferably 0.8 g / mL or less. If the lower limit of this range is not reached, the reaction efficiency may deteriorate, and if it exceeds the upper limit, the stirring efficiency may deteriorate.

〔material〕
As the raw material of the organic compound of the present invention, an appropriate substance may be selected according to the product and the reaction.
Moreover, as a raw material, 1 type may be used independently and 2 or more types may be used together by arbitrary combinations and a ratio. For example, in order to obtain a product by a synthesis reaction or the like, usually two or more kinds of materials are used as raw materials. For example, in order to obtain a product by a decomposition reaction or the like, usually only one kind of raw material may be used.
Further, the amount of the raw material used may be arbitrarily set as appropriate.

〔reaction〕
What is necessary is just to set the reaction advanced in the manufacturing method of this invention according to a product and a raw material. However, in the production method of the present invention, a reaction in which the carbonate according to the present invention can be used as a reaction accelerator is performed. That is, by allowing carbonate to exist in the reaction system, a reaction in which the carbonate can act as a reaction accelerator is performed.
In this case, the reaction may be appropriately selected from various reactions such as synthesis reaction and decomposition reaction, and examples thereof include alkylation, amination, alkenylation, etherification, esterification reaction and the like. Among these, preferred forms are arylation, methylation, methoxylation, amination reaction and the like.

Specific examples include secondary amine or tertiary amine synthesis reaction by reaction of amine compound and halogen compound, amine compound synthesis reaction by reaction of amide compound and halogen compound, reaction of hydroxy group and halogen compound. Examples include ether compound synthesis reaction, ether compound synthesis reaction by reaction of hydroxy group and alkylating agent, and the like.
In the production method of the present invention, one type of reaction may be performed in the reaction system in which carbonate is present, but two or more types of reaction may be performed. However, from the viewpoint of increasing the purity of the product, it is preferable that the proceeding reaction is one type.

[Other reaction accelerators, etc.]
In the production method of the present invention, an appropriate reaction accelerator can be used in combination with the carbonate, depending on the reaction. As examples of other reaction accelerators, a palladium catalyst, a copper catalyst, a nickel catalyst, a rhodium catalyst, a zinc catalyst, and the like can be used in combination when performing an amine compound synthesis reaction and an ether compound synthesis reaction.
It is also preferable to use an appropriate ligand for improving the activity of the reaction accelerator. Examples of ligands include phosphine ligands, amine ligands, sulfur-based ligands, oxygen-based ligands, and the like.
Furthermore, you may make an additive coexist in a reaction system suitably.
In addition, the above other reaction accelerators, ligands, additives and the like may be used alone or in combination of two or more in any combination and ratio.

[Reaction temperature]
In the production method of the present invention, the reaction temperature for carrying out the reaction is arbitrary as long as the effects of the present invention are not significantly impaired. However, in practice, it is desirable that the temperature is usually −10 ° C. or higher and usually 250 ° C. or lower.

Especially, when manufacturing an amine compound, it is preferable that reaction temperature is 35 degreeC or more and 240 degrees C or less.
In addition, when producing an arylamine compound (for example, a coupling reaction between an amine compound and an aryl compound), the reaction temperature is usually 90 ° C. or higher, preferably 100 ° C. or higher, and usually 240 ° C. or lower. Preferably it is 150 degrees C or less. However, when 0-valent copper is used in combination with carbonate as another reaction accelerator, the temperature is preferably 135 ° C. or higher and 220 ° C. or lower.

Furthermore, when manufacturing an ether compound, it is preferable that reaction temperature is 30 degreeC or more and 100 degrees C or less.
Moreover, when manufacturing an aryl compound (for example, coupling reaction of an aryl compound and an aryl compound), it is preferable that reaction temperature is -5 degreeC or more and 150 degrees C or less.
Furthermore, when manufacturing an alkene compound, the reaction temperature is preferably −10 ° C. or higher and 30 ° C. or lower.

[Reaction solvent]
The reaction may be performed without a solvent, but may be performed in a reaction solvent. When a reaction solvent is used, the reaction solvent is not particularly limited as long as it is a solvent that is substantially inert to the reaction. However, as the reaction solvent, a solvent having a boiling point higher than the reaction temperature of the reaction is preferable from the standpoint of production.

  Examples of reaction solvents include aromatic hydrocarbons such as toluene and xylene; aliphatic hydrocarbons such as hexane, cyclohexane and heptane; halogenated hydrocarbons such as chlorobenzene, dichlorobenzene, chloroform and 1,2-dichloroethane; THF Ethers such as (tetrahydrofuran), diethyl ether and diisopropyl ether; ketones such as methyl ethyl ketone and methyl isobutyl ketone; alcohols such as methanol, ethanol and 2-propanol; N, N-dimethylformamide, N-methyl 2-pyrrolidone and the like Amides; sulfoxides such as dimethyl sulfoxide; nitriles such as acetonitrile.

  Furthermore, when potassium carbonate is used as the carbonate, the relative permittivity of the reaction solvent is usually 2 or more and usually 50 or less, preferably 40 or less because of the compatibility between potassium carbonate and the reaction solvent. Preferably, it is 30 or less, more preferably 20 or less. If the relative dielectric constant is below the lower limit of the above range, the reaction efficiency may be deteriorated, and if it exceeds the upper limit, the stirring efficiency may be deteriorated due to an increase in slurry viscosity.

In addition, when using a reaction solvent, the reaction solvent may be used individually by 1 type, and may use 2 or more types together by arbitrary combinations and ratios.
Furthermore, when using a reaction solvent, the usage-amount is arbitrary. However, it is usually 10 times by weight or less, preferably 5 times by weight or less, more preferably 3 times by weight or less with respect to the organic compound as the product. By making the amount used within this range, it is possible to increase the reaction yield. In addition, when the reaction is carried out without a solvent, the yield can be further increased.

[Operation during reaction]
In the production method of the present invention, the reaction is carried out at a predetermined reaction temperature in a reaction system in which raw materials and carbonates, and appropriately used reaction solvents, other reaction accelerators, ligands, additives, etc. coexist. Proceed to produce the product organic compound.
When carrying out the reaction, the order of mixing the components present in the reaction system is arbitrary, and the components may be mixed at once or in two or more portions. Furthermore, during the reaction, arbitrary operations such as stirring, degassing and refluxing may be appropriately performed.

[Product]
The production method of the present invention can be used in the production of any organic compound using a carbonate. Therefore, the product (organic compound) produced by the production method of the present invention is not particularly limited.
Examples of organic compounds suitable for production by the production method of the present invention include amine compounds, aryl compounds, ether compounds, alkene compounds, ester compounds and the like. Therefore, it is desirable to produce as a product at least one selected from the group consisting of these amine compounds, aryl compounds, ether compounds, alkene compounds, and ester compounds. In particular, the production of amine compounds and aryl compounds is highly effective when considering the performance of the final product.
Note that the amine compounds, aryl compounds, ether compounds, alkene compounds, and ester compounds described above are suitable for use as electronic materials.

〔yield〕
According to the production method of the present invention, a desired organic compound can be produced in a high yield. The specific yield varies depending on the raw material, reaction type, reaction conditions, etc., but is usually 80% or more, preferably 90% or more. The upper limit of the yield is not limited, but is theoretically 100%.

〔purity〕
According to the production method of the present invention, a desired organic compound can be produced with high purity. The specific purity varies depending on the raw material, the type of reaction, reaction conditions, and the like, but is usually 70% or more, preferably 80% or more. The upper limit of purity is not limited, but is theoretically 100%.

〔effect〕
As described above, the yield and purity of the reaction can be increased by allowing a carbonate having a predetermined number average particle diameter to be present in the reaction system.

[II. Electronic materials]
Since the organic compound produced by the production method of the present invention described above is excellent in terms of purity, it can be used as an electronic material. For example, it is suitable for use as a material for an electronic device described later.
Among them, examples of the electronic material that can be preferably manufactured by the manufacturing method of the present invention include charge transport materials having charge transport properties. Among charge transport materials, amine compounds, aryl compounds, ether compounds, alkene compounds, and ester compounds are particularly preferable, and arylamine compounds are more preferable because they exhibit particularly large effects.

When the specific example of an electronic material is given, the compound which has the structure shown below is mentioned. That is, examples of the arylamine compound include compounds having a structure represented by the following structural formula (I). Examples of the ether compound include compounds having a structure represented by the following structural formula (II). Furthermore, examples of the alkene compound include compounds having a structure represented by the following structural formula (III). Examples of the ester structure include a compound having a structure represented by the following structural formula (III) or a compound having a structure represented by the following structural formula (IV).

In the above structural formulas (I) to (IV), Ar ¹ to Ar ³ and Ar ⁵ each independently represent an aryl group which may have a substituent. Ar ⁴ represents an arylene group which may have a substituent. R ¹ to R ⁷ each independently represents a hydrogen atom, an alkyl group or an aryl group which may have a substituent, or an ester group. Ar ¹ to Ar ⁵ and R ¹ to R ⁵ may have a ring structure directly or through a linking group.

  The electronic material manufactured by the manufacturing method of the present invention as described above can exhibit high performance when used in an electronic device, an image forming apparatus, or the like.

[III. Electronic device]
The above electronic materials can be widely used as materials for electronic devices. Examples of such electronic devices include electrophotographic photoreceptors (photoconductors), electroluminescent elements, transistors, capacitors, liquid crystals, electrochromic media, recording media, and the like. Of these, it is particularly preferred to be used for an electrophotographic photosensitive member, an electroluminescent element and the like.
Hereinafter, an electrophotographic photoreceptor will be described as an example of the electronic device.

[Electrophotographic photoconductor]
The electrophotographic photoreceptor is configured to have a photosensitive layer on a conductive support. When the electronic material produced by the method for producing an organic compound of the present invention is applied to this electrophotographic photoreceptor, the electronic material is contained in the photosensitive layer.

The outline of the electrophotographic photosensitive member is as follows. That is, the photosensitive layer of the electrophotographic photosensitive member is provided on the conductive support, and if it has an undercoat layer, it is provided on the undercoat layer (that is, on the conductive support via the undercoat layer). .
As the type of the photosensitive layer, it may be formed as a vapor-deposited film. Usually, however, a type (single-layer type) photosensitive material in which the charge generation material and the charge transport material are present in the same layer and dispersed in the binder resin. Layer: a type having a multilayer structure in which a charge generation material is dispersed in a binder resin and a charge transport layer in which a charge transport material is dispersed in a binder resin (multilayer type). Or a functional separation type) photosensitive layer. A photoreceptor having a single layer type photosensitive layer is a so-called single layer type photoreceptor, and a photoreceptor having a laminated type photosensitive layer is a so-called laminated type photoreceptor (or a function separation type photoreceptor). Any photosensitive layer may be used. Further, an overcoat layer (protective layer) may be provided on the photosensitive layer for the purpose of improving the chargeability and improving the wear resistance.

  Further, as the laminated photosensitive layer, a charge generating layer and a charge transport layer are laminated in this order from the conductive support side, and a charge transport layer and a charge generation layer are laminated in this order. There are reverse laminated type photosensitive layers, and any of them can be adopted. However, among these, a normal lamination type photosensitive layer that can exhibit the most balanced photoconductivity is preferable.

[Conductive support]
There are no particular restrictions on the conductive support used for the photoreceptor, but for example, a metal material such as aluminum, aluminum alloy, stainless steel, copper, nickel, etc .; conductive powder mixed with metal, carbon, tin oxide, etc. A resin material, glass, paper, or the like obtained by depositing or coating a conductive material such as aluminum, nickel, or ITO (indium tin oxide) on the surface thereof is mainly used. Moreover, these may be used individually by 1 type and may use 2 or more types together by arbitrary combinations and a ratio. As the form, for example, a drum shape, a sheet shape, a belt shape or the like is used. Further, a conductive material having an appropriate resistance value may be coated on a conductive support made of a metal material in order to control conductivity and surface properties or to cover defects.

Moreover, when using metal materials, such as an aluminum alloy, as an electroconductive support body, you may use, after giving an anodic oxide film. Although there is no restriction | limiting in the formation method of an anodized film, For example, an anodized film can be formed by anodizing in acidic baths, such as chromic acid, a sulfuric acid, an oxalic acid, boric acid, sulfamic acid. Among these, anodizing treatment in sulfuric acid gives better results. In the case of anodic oxidation in sulfuric acid, the sulfuric acid concentration is 100 to 300 g / L, the dissolved aluminum concentration is 2 to 15 g / L, the liquid temperature is 15 to 30 ° C., the electrolysis voltage is 10 to 20 V, and the current density is 0.5 to Although it is preferable to set within the range of ² A / dm ² , it is not limited to the above conditions.

  Furthermore, it is preferable to perform a sealing treatment on the anodic oxide film thus formed. The sealing treatment may be carried out by a known method. For example, it is immersed in an aqueous solution containing nickel fluoride as a main component, or immersed in an aqueous solution containing nickel acetate as a main component. It is preferable that high temperature sealing treatment is performed.

  The concentration of the nickel fluoride aqueous solution used in the case of the low-temperature sealing treatment can be appropriately selected, but more preferable results are obtained when it is used in the range of 3 to 6 g / L. In order to smoothly proceed with the low-temperature sealing treatment, the treatment temperature is usually 25 ° C. or higher, preferably 30 ° C. or higher, and usually 40 ° C. or lower, preferably 35 ° C. or lower. Furthermore, the pH of the aqueous nickel fluoride solution used during the low-temperature sealing treatment is usually 4.5 or higher, preferably 5.5 or higher, and usually 6.5 or lower, preferably 6.0 or lower. . As the pH adjuster, oxalic acid, boric acid, formic acid, acetic acid, sodium hydroxide, sodium acetate, aqueous ammonia and the like can be used. Moreover, it is preferable to process in the range for 1-3 minutes per 1 micrometer of film thickness of the film for the processing time of the low temperature sealing treatment. In order to further improve the physical properties of the film, for example, cobalt fluoride, cobalt acetate, nickel sulfate, a surfactant or the like may be contained in the nickel fluoride aqueous solution. Moreover, after immersion, it is washed with water and dried to finish the low temperature sealing treatment.

On the other hand, as the sealing agent in the case of the high-temperature sealing treatment, for example, an aqueous metal salt solution such as nickel acetate, cobalt acetate, lead acetate, nickel acetate-cobalt, and barium nitrate can be used. Of these, nickel acetate is particularly preferred.
When using nickel acetate aqueous solution, it is preferable to use the concentration within a range of 5 to 20 g / L. The treatment temperature is usually 80 ° C. or higher, preferably 90 ° C. or higher, and usually 100 ° C. or lower, preferably 98 ° C. or lower. Furthermore, it is preferable to process the pH of nickel acetate aqueous solution in the range of 5.0-6.0. Here, as the pH adjuster, for example, ammonia water, sodium acetate, or the like can be used. The treatment time is usually 10 minutes or longer, preferably 20 minutes or longer. In this case, sodium acetate, an organic carboxylic acid, an anionic or nonionic surfactant may be contained in the nickel acetate aqueous solution in order to improve the film properties. Moreover, after immersion, it is washed with water and dried to finish the high temperature sealing treatment.

  Further, when the average film thickness of the anodized film is thick, it is desirable to perform the sealing treatment under strong sealing conditions by increasing the concentration of the sealing liquid and performing the treatment at a high temperature for a long time. Therefore, when the average film thickness of the anodized film is thick, productivity may be deteriorated and surface defects such as spots, dirt, and dusting are likely to occur on the surface of the film. From such a point, it is preferable that the average film thickness of the anodic oxide coating is usually 20 μm or less, particularly 7 μm or less.

  The support surface may be smooth, or may be roughened by using a special cutting method or polishing. Further, it may be roughened by mixing particles having an appropriate particle diameter with the material constituting the support. In order to reduce the cost, it is possible to use the drawing tube as it is without cutting. In particular, when using a non-cutting aluminum support such as drawing, impact processing, and ironing, the processing eliminates dirt and foreign matter deposits on the surface, small scratches, etc., and a uniform and clean support is obtained. This is preferable.

[Undercoat layer]
An undercoat layer may be provided between the conductive support and the photosensitive layer described later for improving adhesion and blocking properties. As the undercoat layer, a resin, a resin in which particles such as metal oxide (usually inorganic particles) are dispersed, or the like is used.

  Examples of metal oxide particles used for the undercoat layer include metal oxide particles containing one metal element such as titanium oxide, aluminum oxide, silicon oxide, zirconium oxide, zinc oxide, iron oxide, calcium titanate, titanium Examples thereof include metal oxide particles containing a plurality of metal elements such as strontium acid and barium titanate. One kind of these particles may be used alone, or a plurality of kinds of particles may be mixed and used.

  Among these metal oxide particles, titanium oxide and aluminum oxide are preferable, and titanium oxide is particularly preferable. The surface of the titanium oxide particles may be treated with an inorganic substance such as tin oxide, aluminum oxide, antimony oxide, zirconium oxide, or silicon oxide, or an organic substance such as stearic acid, polyol, or silicone. As the crystal form of the titanium oxide particles, any of rutile, anatase, brookite, and amorphous can be used. In addition, the titanium oxide particles may have only one crystal type, or two or more crystal types may be included in any combination and ratio.

  In addition, various particle diameters of the metal oxide particles can be used. Among them, the average primary particle diameter is usually 1 nm or more, preferably 10 nm, from the viewpoint of electrical characteristics and the stability of the coating liquid for forming the undercoat layer. As described above, it is usually 100 nm or less, preferably 50 nm or less.

  The undercoat layer is preferably formed in a state where the metal oxide particles are dispersed in the binder resin. The binder resin used for the undercoat layer is epoxy resin, polyethylene resin, polypropylene resin, acrylic resin, methacrylic resin, polyamide resin, vinyl chloride resin, vinyl acetate resin, phenol resin, polycarbonate resin, polyurethane resin, polyimide resin, chloride Vinylidene resin, polyvinyl acetal resin, vinyl chloride-vinyl acetate copolymer, polyvinyl alcohol resin, polyurethane resin, polyacrylic acid resin, polyacrylamide resin, polyvinyl pyrrolidone resin, polyvinyl pyridine resin, water-soluble polyester resin, cellulose such as nitrocellulose Ester resin, cellulose ether resin, casein, gelatin, polyglutamic acid, starch, starch acetate, amino starch, zirconium chelate compound, zirconium Organozirconium compounds such as alkoxide compounds, titanyl chelate compounds, organic titanyl compounds such as titanyl alkoxide compound, a known binder resin such as a silane coupling agent and the like. These may be used individually by 1 type, or may use 2 or more types together by arbitrary combinations and a ratio. Moreover, you may use with the hardening | curing form with the hardening | curing agent. Among these, alcohol-soluble copolymerized polyamides, modified polyamides, and the like are preferable because they exhibit good dispersibility and coatability.

Further, the use ratio of the particles to the binder resin used for the undercoat layer can be arbitrarily selected, but is usually 10% by weight or more and 500% by weight or less from the viewpoint of dispersion stability and coatability. It is preferable to use in a range.
Further, the thickness of the undercoat layer can be arbitrarily selected, but is usually preferably in the range of 0.1 μm or more and 20 μm or less from the viewpoint of improving the photoreceptor characteristics and applicability.
Moreover, you may make an undercoat layer contain an additive suitably. For example, a known antioxidant or the like may be mixed in the undercoat layer. Furthermore, for the purpose of preventing image defects, pigment particles, resin particles, and the like may be contained and used.

(Photosensitive layer)
The photosensitive layer formed on the conductive support may have a single layer structure in which the charge generation material and the charge transport material are present in the same layer and dispersed in the binder resin. It may have a laminated structure in which the charge generation layer in which the generation material is dispersed in the binder and the charge transport layer in which the charge transport material is dispersed in the binder resin are functionally separated.

(Charge generation layer)
The charge generation layer of the multilayer photoconductor contains a charge generation material and usually contains a binder resin and other components used as necessary.
Such a charge generation layer is usually prepared by dispersing a charge generation substance in a solution obtained by dissolving a binder resin (binder resin) in an organic solvent, and applying this onto a conductive support, It is formed by binding fine particles of a charge generation material and various binder resins.

  Any known charge generating substance can be used, and examples thereof include selenium and its alloys, cadmium sulfide, other inorganic photoconductive materials, and organic photoconductive materials such as organic pigments. Of these, organic photoconductive materials are preferred, and organic pigments are particularly preferred. Specific examples of organic pigments include phthalocyanine pigments (phthalocyanine compounds), azo pigments, perylene pigments, quinacridone pigments, polycyclic quinone pigments, indigo pigments, benzimidazole pigments, pyrylium pigments, thiapyrylium pigments, squalene pigments, dithioketo. Examples include pyrrolopyrrole pigments and anthanthrone pigments.

Among the organic pigments exemplified above, the charge generating substance is particularly preferably a phthalocyanine pigment or an azo pigment, more preferably a phthalocyanine pigment, and particularly preferably an oxytitanium phthalocyanine pigment.
The oxytitanium phthalocyanine pigment can be used in various crystal forms as well as in an amorphous form. Among them, oxytitanium phthalocyanine characterized by showing a clear peak at a Bragg angle (2θ ± 0.2 °) of 27.1 ° or 27.3 ° in a powder X-ray diffraction spectrum using CuKα as a radiation source is It has a very high charge generation efficiency, and can be more suitably used as a charge generation material.
In addition, a charge generation material may be used individually by 1 type, and may use 2 or more types together by arbitrary combinations and a ratio.

  Moreover, there is no restriction | limiting in binder resin used for an electric charge generation layer, Arbitrary resin can be used. Specific examples thereof include polyvinyl butyral resins, polyvinyl formal resins, polyvinyl acetal resins such as partially acetalized polyvinyl butyral resins in which a part of butyral is modified with formal or acetal, polyarylate resins, polycarbonate resins, polyester resins, Modified ether polyester resin, phenoxy resin, polyvinyl chloride resin, polyvinylidene chloride resin, polyvinyl acetate resin, polystyrene resin, acrylic resin, methacrylic resin, polyacrylamide resin, polyamide resin, polyvinyl pyridine resin, cellulose resin, polyurethane resin , Epoxy resin, silicone resin, polyvinyl alcohol resin, polyvinyl pyrrolidone resin, casein, vinyl chloride-vinyl acetate copolymer, hydroxy-modified vinyl chloride -Vinyl acetate copolymer, carboxyl-modified vinyl chloride-vinyl acetate copolymer, vinyl chloride-vinyl acetate copolymer such as vinyl chloride-vinyl acetate-maleic anhydride copolymer, styrene-butadiene copolymer, chloride Insulating resins such as vinylidene-acrylonitrile copolymers, styrene-alkyd resins, silicon-alkyd resins, phenol-formaldehyde resins, and organic photoconductive polymers such as poly-N-vinylcarbazole, polyvinylanthracene, and polyvinylperylene. However, it is not limited to these polymers. In addition, these binder resins may be used individually by 1 type, or may mix and use 2 or more types by arbitrary combinations and a ratio.

  There is no particular limitation on the solvent and dispersion medium used for preparing the coating liquid by dissolving the binder resin, and any solvent and dispersion medium can be used. Specific examples thereof include saturated aliphatic solvents such as pentane, hexane, octane and nonane; aromatic solvents such as toluene, xylene and anisole; halogenated aromatic solvents such as chlorobenzene, dichlorobenzene and chloronaphthalene; Amide solvents such as dimethylformamide and N-methyl-2-pyrrolidone; Alcohol solvents such as methanol, ethanol, isopropanol, n-butanol and benzyl alcohol; Aliphatic polyhydric alcohols such as glycerin and polyethylene glycol; Acetone and cyclohexanone Chain and cyclic ketone solvents such as methyl ethyl ketone; ester solvents such as methyl formate, ethyl acetate, n-butyl acetate; halogenated hydrocarbon solvents such as methylene chloride, chloroform, 1,2-dichloroethane; diethyl ether , Chain and cyclic ether solvents such as methoxyethane, tetrahydrofuran, 1,4-dioxane, methyl cellosolve, ethyl cellosolve; aprotic polar solvents such as acetonitrile, dimethyl sulfoxide, sulfolane, hexamethylphosphate triamide; n -Nitrogen-containing compounds such as butylamine, isopropanolamine, diethylamine, triethanolamine, ethylenediamine, triethylenediamine, triethylamine; mineral oil such as ligroin; water and the like. Among these, those that do not dissolve the above-described undercoat layer are preferably used. Moreover, these may be used individually by 1 type and may use 2 or more types together by arbitrary combinations and a ratio.

Further, in the charge generation layer, the blending ratio (weight) of the binder resin and the charge generation material is not limited, but the charge generation material is usually 10 parts by weight or more, preferably 30 parts with respect to 100 parts by weight of the binder resin. It is usually not less than 1000 parts by weight, preferably not more than 500 parts by weight. If the ratio of the charge generation material is too high, the stability of the coating solution may decrease due to aggregation of the charge generation material, while if too low, the sensitivity as a photoreceptor may decrease. It is preferable to use in the said range.
The thickness of the charge generation layer is not limited, but is usually 0.1 μm or more, preferably 0.15 μm or more, and usually 4 μm or less, preferably 0.6 μm or less.

In addition, the charge generation layer has well-known antioxidants, plasticizers, UV absorbers, electron suction to improve film formability, flexibility, coating properties, stain resistance, gas resistance, light resistance, etc. Additives such as an organic compound, a leveling agent, and a visible light shading agent may be contained. Moreover, you may make the photosensitive layer contain various additives, such as a leveling agent for improving applicability | paintability, antioxidant, and a sensitizer as needed. Examples of the antioxidant include hindered phenol compounds and hindered amine compounds. Examples of dyes and pigments include various pigment compounds and azo compounds. Examples of surfactants include silicone oil and fluorine-based oil.
In addition, as a method for dispersing the charge generation material, a known dispersion method such as a ball mill dispersion method, an attritor dispersion method, or a sand mill dispersion method can be used. At this time, it is effective to make the particles finer to a particle size of 0.5 μm or less, preferably 0.3 μm or less, more preferably 0.15 μm or less.

(Charge transport material)
The charge transport layer of the multilayer photoconductor contains a charge transport material and usually contains a binder resin and other components used as necessary. Specifically, such a charge transport layer is prepared by, for example, dissolving or dispersing a charge transport material and a binder resin in a solvent (solvent, dispersion medium) to prepare a coating solution, which is used as a layered photosensitive layer. It can be obtained by coating and drying on the charge generation layer in the case of coating, or on the conductive support in the case of the reverse lamination type photosensitive layer (on the undercoating layer in the case of providing the undercoating layer).

  The charge transport material is not particularly limited, and any material can be used. Examples of known charge transport materials include aromatic nitro compounds such as 2,4,7-trinitrofluorenone, cyano compounds such as tetracyanoquinodimethane, electron withdrawing materials such as quinone compounds such as diphenoquinone, and carbazole derivatives. , Indole derivatives, imidazole derivatives, oxazole derivatives, pyrazole derivatives, thiadiazole derivatives, heterocyclic compounds such as benzofuran derivatives, aniline derivatives, hydrazone derivatives, aromatic amine derivatives, stilbene derivatives, butadiene derivatives, enamine derivatives and multiple types of these compounds Or an electron donating substance such as a polymer having a group composed of these compounds in the main chain or side chain. Among these, carbazole derivatives, aromatic amine derivatives, stilbene derivatives, butadiene derivatives, enamine derivatives, and those obtained by bonding a plurality of these compounds are preferable. Any one of these charge transport materials may be used alone, or two or more thereof may be used in any combination and ratio.

  Moreover, there is no restriction | limiting in binder resin used for an electric charge transport layer, Arbitrary things can be used. For example, the same materials as those exemplified as the binder resin for the charge generation layer can be used. However, preferably, a polycarbonate resin, a polyarylate resin, and a polyester resin are used, and more preferably, a polycarbonate resin and a polyarylate resin are used.

  The ratio of the binder resin and the charge transport material used in the charge transport layer is usually 20 parts by weight or more of the charge transport material with respect to 100 parts by weight of the binder resin, and 30 parts by weight from the viewpoint of reducing the residual potential. The above is preferable, and 40 parts by weight or more is more preferable from the viewpoint of stability and charge mobility during repeated use. On the other hand, it is usually 150 parts by weight or less from the viewpoint of thermal stability of the photosensitive layer, preferably 120 parts by weight or less from the viewpoint of compatibility between the charge transport material and the binder resin, and 100 parts by weight from the viewpoint of printing durability. Part or less is more preferable, and from the viewpoint of scratch resistance, 80 parts by weight or less is particularly preferable.

The film thickness of the charge transport layer is also arbitrary, but it is usually used in the range of 5 μm to 50 μm, preferably 10 μm to 45 μm from the viewpoint of long life and image stability, and 10 μm to 30 μm from the viewpoint of high resolution. More preferred.
Further, the charge transport layer may contain an additive. Examples of the additive include those similar to those of the charge generation layer.

[Single-layer type photosensitive layer]
In addition to the charge generation material and the charge transport material, the photosensitive layer of the single-layer photoconductor is formed using a binder resin in order to ensure film strength, in the same manner as the charge transport layer of the multilayer photoconductor. Specifically, usually, a charge generation material, a charge transport material, and various binder resins are dissolved or dispersed in a solvent or a dispersion medium to prepare a coating solution, and on the photoreceptor substrate (when an undercoat layer is provided) It can be obtained by coating and drying on the undercoat layer.

In the single-layer type photosensitive layer, the types of the charge transport material and the binder resin, and the use ratio thereof are the same as those described for the charge transport layer of the multilayer photoreceptor.
In the single-layer type photosensitive layer, a charge generating material is further dispersed in the charge transport medium comprising the charge transport material and the binder resin. As the charge generation material, the same materials as those described for the charge generation layer of the multilayer photoreceptor can be used. However, in the case of a photosensitive layer of a single layer type photoreceptor, it is desirable to sufficiently reduce the particle size of the charge generating material. Specifically, the range is usually 1 μm or less, preferably 0.5 μm or less.

Further, if the amount of the charge generating material dispersed in the single-layer type photosensitive layer is too small, sufficient sensitivity may not be obtained, and if it is too large, the chargeability may be lowered or the sensitivity may be lowered. Therefore, in the single layer type photoreceptor, the content of the charge generating substance is usually 0.1% by weight or more, preferably 1% by weight or more, and usually 50% by weight or less, preferably 20% by weight or less. .
Further, the film thickness of the photosensitive layer of the single layer type photoreceptor is usually 5 μm or more, preferably 10 μm or more, and usually 100 μm or less, preferably 50 μm or less.
Further, the single layer type photosensitive layer may contain an additive. Examples of the additive include those similar to those of the charge generation layer.

[Other layers]
Further, other layers than the above-described charge generation layer, charge transport layer, and single-layer type photosensitive layer may be further provided.
For example, a protective layer may be provided on the outermost surface layer of the photosensitive member for the purpose of preventing the photosensitive layer from being worn out or preventing or reducing the deterioration of the photosensitive layer due to a discharge substance generated from a charger or the like.

  The protective layer can be formed by containing a conductive material in an appropriate binder resin. Further, the protective layer may be formed using a copolymer using a compound having a charge transporting ability such as a triphenylamine skeleton as described in JP-A-9-190004 and JP-A-10-252377. it can. Examples of the conductive material include aromatic amino compounds such as TPD (N, N′-diphenyl-N, N′-bis- (m-tolyl) benzidine), antimony oxide, indium oxide, tin oxide, titanium oxide, and tin oxide. -Metal oxides such as antimony oxide, aluminum oxide, and zinc oxide can be used, but are not limited thereto.

  The binder resin used for the protective layer is not limited, but examples thereof include polyamide resin, polyurethane resin, polyester resin, epoxy resin, polyketone resin, polycarbonate resin, polyvinyl ketone resin, polystyrene resin, polyacrylamide resin, and siloxane resin. Known resins can be used. Also, a copolymer of a skeleton having a charge transporting ability such as a triphenylamine skeleton as described in JP-A-9-190004 and JP-A-10-252377 and the above resin can be used.

The protective layer is preferably configured to have an electric resistance of 10 ⁹ Ω · cm to 10 ¹⁴ Ω · cm. When the electric resistance is higher than the upper limit of the above range, the residual potential increases, and an image formed using the photoconductor may be an image with much fog. On the other hand, when the value is lower than the lower limit of the above range, there is a possibility that the image formed using the photoconductor may be blurred or the resolution may be lowered. However, the protective layer is configured so as not to substantially prevent transmission of light irradiated for image exposure.

  In addition, fluorine resin, silicone resin, polyethylene resin, polystyrene resin, etc. are used for the surface layer for the purpose of reducing frictional resistance and abrasion on the surface of the photoconductor and increasing the transfer efficiency of the toner from the photoconductor to the transfer belt and paper. May be included. Moreover, the particle | grains which consist of these resin, and the particle | grains of an inorganic compound may be included.

[Example of specific layer forming method]
Each layer constituting the photoconductor is formed by sequentially applying a coating solution containing the material constituting each layer on the support using a known coating method and repeating the coating and drying process for each layer. Is done.

  In the case of a photosensitive layer of a single layer type photoreceptor and a charge transport layer of a laminated type photoreceptor, the coating liquid for layer formation has a solid content concentration of usually 5% by weight or more, preferably 10% by weight or more, Further, it is usually 40% by weight or less, preferably 35% by weight or less. Further, the viscosity of the coating solution is usually in the range of 10 mPa · s or more, preferably 50 mPa · s or more, usually 500 mPa · s or less, preferably 400 mPa · s or less.

  On the other hand, in the case of a charge generating layer of a laminated photoreceptor, the coating solution for forming a layer has a solid concentration of usually 0.1% by weight or more, preferably 1% by weight or more, and usually 15% by weight or less. Preferably, it is 10% by weight or less. The viscosity of the coating solution is usually 0.01 mPa · s or higher, preferably 0.1 mPa · s or higher, usually 20 mPa · s or lower, preferably 10 mPa · s or lower.

There is no restriction | limiting in the coating method of a coating liquid. Examples include dip coating, spray coating, spinner coating, bead coating, wire bar coating, blade coating, roller coating, air knife coating, curtain coating, etc. It is also possible to use a coating method.
There is no restriction | limiting also in the drying method of a coating liquid. However, it is preferable to dry by heating in the temperature range of 30 to 200 ° C. for 1 minute to 2 hours with no wind or ventilation after finger touch drying at room temperature. Further, the heating temperature may be constant or may be changed while drying.

[Applicable parts of electronic materials]
As described above, electronic materials manufactured by the manufacturing method of the present invention often have unique electrical properties. Therefore, in the photoreceptor using the electronic material, the electronic material is preferably contained in a photosensitive layer (single-layer type photosensitive layer, charge generation layer, charge transport layer). Therefore, in the production method of the present invention, it is preferable to produce the above-described charge generation material, charge transport material, binder or additive. When the photosensitive layer has a laminated structure, the electronic material may be contained in either the charge generation layer or the charge transport layer, but is more preferably contained in the charge transport layer as a charge transport material. .

An electrophotographic photosensitive member using an electronic material using the method for producing an organic compound of the present invention as described above is particularly excellent in initial electricity, fast in mobility, and excellent in repeated durability.
In addition, other electronic devices using the electronic material are also expected to exhibit excellent performance.

[IV. Image forming apparatus]
Next, an embodiment of an image forming apparatus using the electrophotographic photosensitive member of the present invention (an image forming apparatus of the present invention) will be described with reference to FIG. However, the embodiment is not limited to the following description, and can be arbitrarily modified without departing from the gist of the present invention.

As shown in FIG. 1, the image forming apparatus includes an electrophotographic photosensitive member 1, a charging device (charging unit) 2, an exposure device (exposure unit) 3, and a developing device (developing unit) 4. Accordingly, a transfer device (transfer portion) 5, a cleaning device (cleaning portion) 6, and a fixing device (fixing portion) 7 are provided.
The electrophotographic photosensitive member 1 is not particularly limited as long as it is the above-described electrophotographic photosensitive member. In FIG. 1, as an example, a drum-shaped photosensitive member in which the above-described photosensitive layer is formed on the surface of a cylindrical conductive support. Showing the body. A charging device 2, an exposure device 3, a developing device 4, a transfer device 5, and a cleaning device 6 are arranged along the outer peripheral surface of the electrophotographic photoreceptor 1.

  The charging device 2 charges the electrophotographic photosensitive member 1 and uniformly charges the surface of the electrophotographic photosensitive member 1 to a predetermined potential. Examples of the charging device include a corona charging device such as a corotron and a scorotron, a direct charging device (contact type charging device) that charges a direct charging member to which a voltage is applied by contacting the photosensitive member surface, and a contact type charging device such as a charging brush. Often used. Examples of direct charging means include contact chargers such as charging rollers and charging brushes. In FIG. 1, a roller-type charging device (charging roller) is shown as an example of the charging device 2.

  As the direct charging means, either charging with air discharge or injection charging without air discharge is possible. It is also possible to adopt an NC roller charging method in which charging is performed in a state where a photosensitive sheet and a charging roller are kept in non-contact at a stable charging distance by winding a resin sheet or the like around the charging roller. Moreover, as a voltage applied at the time of charging, it is possible to use only a direct current voltage or to superimpose alternating current on direct current.

  The type of the exposure apparatus 3 is not particularly limited as long as it can expose the electrophotographic photoreceptor 1 to form an electrostatic latent image on the photosensitive surface of the electrophotographic photoreceptor 1. Specific examples include halogen lamps, fluorescent lamps, lasers such as semiconductor lasers and He—Ne lasers, and LEDs (light emitting diodes). Further, exposure may be performed by a photoreceptor internal exposure method. As the digital electrophotographic system, it is preferable to use a laser, an LED, an optical shutter array, or the like. The light used for the exposure is arbitrary. For example, the exposure may be performed using monochromatic light with a wavelength of 780 nm, monochromatic light with a wavelength slightly shorter than 600 nm to 700 nm, or monochromatic light with a short wavelength of 380 nm to 500 nm. .

  The developing device 4 is not particularly limited as long as the electrostatic latent image formed on the electrophotographic photosensitive member 1 can be developed. Cascade development, one-component insulating toner development, one-component conductive toner development, two-component magnetic brush development Any apparatus such as a dry development system such as a wet development system or the like can be used. In FIG. 1, the developing device 4 includes a developing tank 41, an agitator 42, a supply roller 43, a developing roller 44, and a regulating member 45, and has a configuration in which toner T is stored inside the developing tank 41. .

  Further, a replenishing device (not shown) for replenishing the toner T may be attached to the developing device 4 as necessary. The replenishing device is configured to be able to replenish toner T from a container such as a bottle or a cartridge. The development method may be either a contact method or a non-contact method. As the toner to be used, in addition to the pulverized toner, chemical toners such as suspension granulation, suspension polymerization, and emulsion polymerization aggregation method can be used. In particular, in the case of chemical toners, those having a small particle diameter of about 4 to 8 μm are usually used, and those having a shape that is close to a sphere, or those that are out of a potato or rugby ball shape can also be used. . The polymerized toner is excellent in charging uniformity and transferability and is suitably used for high image quality.

  The supply roller 43 is formed from a conductive sponge or the like. The developing roller 44 is made of a metal roll such as iron, stainless steel, aluminum, or nickel, or a resin roll obtained by coating such a metal roll with a silicon resin, a urethane resin, a fluorine resin, or the like. The surface of the developing roller 44 may be smoothed or roughened as necessary.

  The developing roller 44 is disposed between the electrophotographic photoreceptor 1 and the supply roller 43 and is in contact with the electrophotographic photoreceptor 1 and the supply roller 43, respectively. The supply roller 43 and the developing roller 44 are rotated by a rotation drive mechanism (not shown). The supply roller 43 carries the stored toner T and supplies it to the developing roller 44. The developing roller 44 carries the toner T supplied by the supply roller 43 and contacts the surface of the electrophotographic photosensitive member 1.

The regulating member 45 is formed of a resin blade such as silicon resin or urethane resin, a metal blade such as stainless steel, aluminum, copper, brass, phosphor bronze, or a blade obtained by coating such a metal blade with resin. The regulating member 45 contacts the developing roller 44 and is pressed against the developing roller 44 side with a predetermined force by a spring or the like (a general blade linear pressure is 5 to 500 g / cm). If necessary, the regulating member 45 may be provided with a function of imparting charging to the toner T by frictional charging with the toner T.
The agitator 42 is rotated by a rotation driving mechanism, and agitates the toner T and conveys the toner T to the supply roller 43 side. A plurality of agitators 42 may be provided with different blade shapes and sizes.

  The type of the transfer device 5 is not particularly limited, and an apparatus using an arbitrary system such as an electrostatic transfer method such as corona transfer, roller transfer, or belt transfer, a pressure transfer method, or an adhesive transfer method can be used. . Here, it is assumed that the transfer device 5 includes a transfer charger, a transfer roller, a transfer belt, and the like disposed so as to face the electrophotographic photoreceptor 1. The transfer device 5 applies a predetermined voltage value (transfer voltage) having a polarity opposite to the charging potential of the toner T, and transfers the toner image formed on the electrophotographic photosensitive member 1 to a recording paper (paper, medium) P. Is. The present invention exhibits a greater effect when the transfer voltage is large.

  There is no restriction | limiting in particular about the cleaning apparatus 6, Arbitrary cleaning apparatuses, such as a brush cleaner, a magnetic brush cleaner, an electrostatic brush cleaner, a magnetic roller cleaner, a blade cleaner, can be used. The cleaning device 6 is for scraping off residual toner adhering to the photoreceptor 1 with a cleaning member and collecting the residual toner. However, when there is little or almost no toner remaining on the surface of the photoreceptor, the cleaning device 6 may be omitted.

  The fixing device 7 includes an upper fixing member (fixing roller) 71 and a lower fixing member (fixing roller) 72, and a heating device 73 is provided inside the fixing member 71 or 72. FIG. 1 shows an example in which a heating device 73 is provided inside the upper fixing member 71. As the upper and lower fixing members 71 and 72, known heat fixing members such as a fixing roll in which a metal base tube such as stainless steel or aluminum is coated with silicon rubber, a fixing roll coated with a fluororesin, or a fixing sheet are used. be able to. Further, each of the fixing members 71 and 72 may be configured to supply a release agent such as silicone oil in order to improve releasability, or may be configured to forcibly apply pressure to each other by a spring or the like.

When the toner transferred onto the recording paper P passes between the upper fixing member 71 and the lower fixing member 72 heated to a predetermined temperature, the toner is heated to a molten state and cooled after passing through the recording paper. Toner is fixed on P.
There is no particular limitation on the type of the fixing device, and fixing by any method such as the one used here, heat roller fixing, flash fixing, oven fixing, pressure fixing, IH fixing, belt fixing, IHF fixing, etc. A device can be provided. Note that these fixing methods may be used alone or in combination with a plurality of fixing methods.

In the electrophotographic apparatus configured as described above, an image is recorded as follows.
That is, first, the surface (photosensitive surface) of the photoreceptor 1 is charged to a predetermined potential (for example, −600 V) by the charging device 2. At this time, charging may be performed by a DC voltage, or charging may be performed by superimposing an AC voltage on the DC voltage.
Subsequently, the photosensitive surface of the charged photoreceptor 1 is exposed by the exposure device 3 according to the image to be recorded, and an electrostatic latent image is formed on the photosensitive surface. The developing device 4 develops the electrostatic latent image formed on the photosensitive surface of the photoreceptor 1.

The developing device 4 thins the toner T supplied by the supply roller 43 with a regulating member (developing blade) 45 and has a predetermined polarity (here, the same polarity as the charging potential of the photosensitive member 1) and the negative polarity. ), And conveyed while being carried on the developing roller 44 to be brought into contact with the surface of the photoreceptor 1.
When the charged toner T carried on the developing roller 44 comes into contact with the surface of the photoreceptor 1, a toner image corresponding to the electrostatic latent image is formed on the photosensitive surface of the photoreceptor 1. The toner image is transferred onto the recording paper P by the transfer device 5. Thereafter, the toner remaining on the photosensitive surface of the photoreceptor 1 without being transferred is removed by the cleaning device 6.
After the transfer of the toner image onto the recording paper P, the final image is obtained by passing the fixing device 7 and thermally fixing the toner image onto the recording paper P.

  In addition to the above-described configuration, the image forming apparatus may have a configuration capable of performing, for example, a static elimination process. The neutralization step is a step of neutralizing the electrophotographic photosensitive member by exposing the electrophotographic photosensitive member, and a fluorescent lamp, an LED, or the like is used as the neutralizing device. In addition, the light used in the static elimination process is often light having an exposure energy that is at least three times that of the exposure light.

  The image forming apparatus may be further modified. For example, the image forming apparatus may be configured to perform a pre-exposure process, an auxiliary charging process, or the like, or may be configured to perform offset printing. A full-color tandem system configuration using toner may be used.

  The electrophotographic photosensitive member 1 is combined with one or more of the charging device 2, the exposure device 3, the developing device 4, the transfer device 5, the cleaning device 6, and the fixing device 7 to form an integrated cartridge ( The electrophotographic photosensitive member cartridge may be configured to be detachable from a main body of an electrophotographic apparatus such as a copying machine or a laser beam printer. For example, at least one of the exposure unit 3, the developing unit 4, the transfer unit 5, and the cleaning unit 6 can be integrally supported together with the drum-shaped photoconductor 1 to form a cartridge. In this case, for example, when the electrophotographic photosensitive member 1 and other members are deteriorated, the electrophotographic photosensitive member cartridge is removed from the main body of the image forming apparatus, and another new electrophotographic photosensitive member cartridge is mounted on the main body of the image forming apparatus. This facilitates maintenance and management of the image forming apparatus.

  When an electronic material manufactured by the method for manufacturing an organic compound of the present invention as described above is used, the image forming apparatus is excellent in image characteristics (particularly memory characteristics), and particularly excellent in repetition characteristics. It also excels in changes in image characteristics due to environmental fluctuations. In addition, since it is excellent in fine line reproduction, it is also effective in combination with a polymerized toner.

EXAMPLES Hereinafter, the present invention will be specifically described with reference to examples. However, the present invention is not limited to the following examples, and may be arbitrarily modified and implemented without departing from the gist of the present invention. it can.
In the following description, Et represents an ethyl group, and Ph represents a phenyl group. “Parts” represents “parts by weight” unless otherwise specified. “HPLC” represents “high performance liquid chromatography” unless otherwise specified.

[Production of 4-methoxydiphenylamine]
[Example 1A]
37 g of 4-hydroxydiphenylamine and 50 g of iodinated methane were dissolved in 150 mL of methyl ethyl ketone. To this solution, 70 g of potassium carbonate (FG ground product manufactured by Asahi Glass: number average particle size 55 μm, specific surface area 1.8 m ² / g, bulk density 0.44 g / mL) is added, and the temperature is raised to 75 ° C. for reaction. As a result, it took 24 hours to complete the reaction.
To this, 100 mL of water and 200 mL of toluene were added for liquid separation, and the organic layer was washed 3 times with 100 mL of water. Then, after drying an organic layer with 20 g of magnesium sulfate, the solvent was distilled off. The residue was distilled under reduced pressure to obtain 35 g of 4-methoxydiphenylamine (yield 88%, HPLC purity 97%).

[Example 1B]
37 g of 4-hydroxydiphenylamine and 50 g of iodinated methane were dissolved in 150 mL of methyl ethyl ketone. To this solution, 100 g of potassium carbonate (FG-R10 manufactured by Asahi Glass: number average particle diameter 11 μm, specific surface area 2.0 m ² / g, bulk density 0.29 g / mL) was added and refluxed to react. It took two days to finish.
To this, 100 mL of water and 200 mL of toluene were added for liquid separation, and the organic layer was washed 3 times with 100 mL of water. Then, after drying an organic layer with 20 g of magnesium sulfate, the solvent was distilled off. The residue was distilled under reduced pressure to obtain 30 g of 4-methoxydiphenylamine (yield 83%, HPLC purity 98%).

[Comparative Example 1A]
37 g of 4-hydroxydiphenylamine and 50 g of iodinated methane were dissolved in 150 mL of methyl ethyl ketone. To this solution, 69 g of potassium carbonate (Asahi Glass F: number average particle size 480 μm, specific surface area 0.22 m ² / g, bulk density 1.3 g / mL) was added and reacted under reflux. It took 3 days.
To this, 100 mL of water and 200 mL of toluene were added for liquid separation, and the organic layer was washed 3 times with 100 mL of water. Then, after drying an organic layer with 20 g of magnesium sulfate, the solvent was distilled off. The residue was analyzed by HPLC and ¹ H-NMR. As a result, 5% of the raw material 4-hydroxydiphenylamine remained, and 4-hydroxy-N-methyldiphenylamine was the maximum component (60%). -Methoxydiphenylamine was present in only a small amount (17%). In addition, many components that could not be identified were observed.

[Comparative Example 1B]
37 g of 4-hydroxydiphenylamine and 50 g of iodinated methane were dissolved in 150 mL of methyl ethyl ketone. To this solution, 69 g of potassium carbonate (Kanto Chemical deer grade: number average particle size 0.8 mm) was added and reacted for 7 days under reflux.
To this, 100 mL of water and 200 mL of toluene were added for liquid separation, and the organic layer was washed 3 times with 100 mL of water. Then, after drying an organic layer with 20 g of magnesium sulfate, the solvent was distilled off. The residue was analyzed by HPLC and ¹ H-NMR. As a result, 5% of the raw material 4-hydroxydiphenylamine remained, and 4-hydroxy-N-methyldiphenylamine was the maximum component (80%). -Methoxydiphenylamine was present only in trace amounts (2%). Moreover, many components which cannot be identified more than Comparative Example 1A were recognized.

[Production of N- (4-isopropylphenyl) N, N-diphenylamine]
[Example 2]
16.9 g of diphenylamine and 30 g of 4-iodocumene were dissolved in 50 mL of nitrobenzene. To this solution, 25 g of potassium carbonate (Asahi Glass pulverized product: number average particle size 26 μm, specific surface area 0.6 m ² / g, bulk density 0.66 g / mL) and metal copper powder 5 g were added, and the temperature was raised to 210 ° C. And reacted for 9 hours.
To this, 200 mL of water and 200 mL of toluene were added for liquid separation, and the organic layer was washed 3 times with 100 mL of water. Then, after drying an organic layer with 20 g of magnesium sulfate, the solvent was distilled off. The residue was distilled under reduced pressure to obtain 24.5 g of N- (4-isopropylphenyl) N, N-diphenylamine (yield 85%, HPLC purity 96%).

[Comparative Example 2]
16.9 g of diphenylamine and 30 g of 4-iodocumene were dissolved in 50 mL of nitrobenzene. To this solution was added 25 g of potassium carbonate (Kanto Chemical deer grade: number average particle size 0.8 mm) and 5 g of copper metal powder, and the temperature was raised to 210 ° C. and reacted for 2 days.
To this, 200 mL of water and 200 mL of toluene were added for liquid separation, and the organic layer was washed 3 times with 100 mL of water. Then, after drying an organic layer with 20 g of magnesium sulfate, the solvent was distilled off. The residue was distilled under reduced pressure to obtain 22 g of N- (4-isopropylphenyl) N, N-diphenylamine (yield 77%, HPLC purity 95%).

[Production of N, N, N-tris (p-tolyl) amine]
Example 3
10.7 g of p-toluidine, 30 g of p-iodotoluene, 25 g of potassium carbonate (Asahi Glass pulverized product: number average particle size 26 μm, specific surface area 0.6 m ² / g, bulk density 0.66 g / mL), and metallic copper The powder 5g was added in the four necked flask, it heated up to 210 degreeC, and was made to react for 9 hours.
To this, 200 mL of water and 200 mL of toluene were added for liquid separation, and the organic layer was washed with 100 mL of water three times. Then, after drying an organic layer with 20 g of magnesium sulfate, the solvent was distilled off. The residue was distilled under reduced pressure and then purified by flash chromatography (mobile phase: toluene, stationary phase: silica gel 50 g) to obtain 25 g of N, N, N-tris (p-tolyl) amine (yield 87%). HPLC purity 99%).

[Comparative Example 3A]
10.7 g of p-toluidine, 30 g of p-iodotoluene, 25 g of potassium carbonate (Kanto Chemical deer grade: number average particle size 0.8 mm), and 5 g of metallic copper powder are added to a four-necked flask at 210 ° C. The temperature was raised to 9 hours and reacted for 9 hours.
To this, 200 mL of water and 200 mL of toluene were added for liquid separation, and the organic layer was washed with 100 mL of water three times. Then, after drying an organic layer with 20 g of magnesium sulfate, the solvent was distilled off. The residue was distilled under reduced pressure and then purified by flash chromatography (mobile phase: toluene, stationary phase: silica gel 50 g) to obtain 23 g of N, N, N-tris (p-tolyl) amine (yield 80%). HPLC purity 98%).

[Comparative Example 3B]
10.7 g of p-toluidine, 30 g of p-iodotoluene, 25 g of potassium carbonate (FG manufactured by Asahi Glass: number average particle size 0.29 mm, specific surface area 1.3 m ² / g, bulk density 0.9 g / mL), and metal 5 g of copper powder was added to the four-necked flask, heated to 210 ° C., and allowed to react for 8 hours.
To this, 200 mL of water and 200 mL of toluene were added for liquid separation, and the organic layer was washed with 100 mL of water three times. Then, after drying an organic layer with 20 g of magnesium sulfate, the solvent was distilled off. The residue was distilled under reduced pressure and then purified by flash chromatography (mobile phase: toluene, stationary phase: silica gel 50 g) to obtain 23 g of N, N, N-tris (p-tolyl) amine (yield 83%). HPLC purity 98%).

[Production of Ph—CH═CH—CO ₂ Et]
Example 4
(EtO) ₂ P (O) —CH ₂ —CO ₂ Et 0.11 g, benzaldehyde 0.05 g, anthracene 0.10 g (in-system reference), potassium carbonate (FG-F10 manufactured by Asahi Glass: number average particle diameter 11 μm, 1.5 g of a specific surface area of 0.5 m ² / g and a bulk density of 0.61 g / mL is added to a solution of 5 mL of tetrahydrofuran (hereinafter referred to as “THF” where appropriate) containing 0.1 mL of water), and ultrasonic waves are applied for 20 minutes. I took it. When the reaction conversion rate was confirmed by HPLC, the reaction conversion rate (Ph—CH═CH—CO ₂ Et yield) was found to be 85%.

[Comparative Example 4]
(EtO) ₂ P (O) —CH ₂ —CO ₂ Et 0.11 g, benzaldehyde 0.05 g, anthracene 0.10 g (in-system reference), potassium carbonate (Kanto Chemicals deer grade: number average particle size 0. 8 mm) 1.5 g was added to a solution of 5 mL of THF (containing 0.1 mL of water), and ultrasonic waves were applied for 20 minutes. When the reaction was checked by HPLC, the reaction conversion rate (Ph—CH═CH—CO ₂ Et yield) was found to be 40%.

[Production of ethyl triphenylacetate]
Example 5
Potassium carbonate (FG-F20 manufactured by Asahi Glass: number average particle size 19 μm, specific surface area 0.5 m ^{2 /} g) 0.76 g, ethyl iodide 1.6 mL, hexamethylphosphoric triamide (hereinafter referred to as “HMPA” as appropriate) When 1.44 g of triphenylacetic acid was added to a 15 mL mixture and reacted at room temperature, it took 20 hours to complete the reaction.
The reaction mixture was poured into 50 mL of water and extracted twice with 40 mL of ether, and then the ether solution was washed with water. Thereafter, the organic layer was dried with 2 g of sodium sulfate, and then the solvent was distilled off. The residue was washed with hexane to obtain 1.5 g (yield 94%) of the target ethyl triphenylacetate (HPLC purity 99%).

[Comparative Example 5]
When 1.44 g of triphenylacetic acid was added to a mixture of 0.76 g of potassium carbonate (special grade manufactured by Kanto Chemical Co., Ltd .: number average particle size 0.6 mm), 1.6 mL of ethyl iodide and 15 mL of HMPA, the reaction was completed at room temperature. It took 36 hours.
The reaction mixture was poured into 50 mL of water and extracted twice with 40 mL of ether, and then the ether solution was washed with water. Thereafter, the organic layer was dried with 2 g of sodium sulfate, and then the solvent was distilled off. The residue was washed with hexane to obtain 1.4 g (yield 88%) of the target ethyl triphenylacetate (HPLC purity 98%).

[Production of p-acetotoluidine]
Example 6
In a 200 mL four-necked flask equipped with a stirrer and a thermometer at room temperature, 14.9 g (0.10 mol) of p-acetotoluidine, 25.7 g (0.15 mol) of p-bromotoluene, copper iodide (I 1.9 g (0.01 mol), potassium carbonate (FG-R20 manufactured by Asahi Glass: number average particle size 20 μm, specific surface area 1.9 m ² / g, bulk density 0.33 g / mL) 20.7 g (0.15 mol) Were sequentially added and stirred for 10 minutes while flowing nitrogen into the system. Then, it heated to 180 degreeC, and it was made to react by continuing heating at the temperature for 32 hours.
After completion of the reaction, the reaction mixture was cooled to 70 ° C., 100 mL of toluene was added, and the solid content was separated by filtration. When the residual amount of p-acetotoluidine in the filtrate was quantified by HPLC, the reaction conversion rate was 95%.

[Comparative Example 6A]
In a 200 mL four-necked flask equipped with a stirrer and a thermometer at room temperature, 14.9 g (0.10 mol) of p-acetotoluidine, 25.7 g (0.15 mol) of p-bromotoluene, copper iodide (I ) 1.9 g (0.01 mol) and potassium carbonate (special grade manufactured by Kanto Chemical Co., Ltd .: number average particle size 0.6 mm) 20.7 g (0.15 mol) were sequentially added, followed by stirring for 10 minutes while flowing nitrogen into the system. . Then, it heated to 180 degreeC, and it was made to react by continuing heating at the temperature for 45 hours.
After completion of the reaction, the mixture was cooled to 70 ° C., 100 mL of toluene was added, and the solid content was separated by filtration. When the residual amount of p-acetotoluidine in the filtrate was quantified by HPLC, the reaction conversion rate was 85%.

[Comparative Example 6B]
In a 200 mL four-necked flask equipped with a stirrer and a thermometer at room temperature, 14.9 g (0.10 mol) of p-acetotoluidine, 25.7 g (0.15 mol) of p-bromotoluene, copper iodide (I 1.9 g (0.01 mol), potassium carbonate (FG manufactured by Asahi Glass: number average particle size 0.29 mm, specific surface area 1.3 m ² / g, bulk density 0.9 g / mL) 20.7 g (0.15 mol) Were sequentially added and stirred for 10 minutes while flowing nitrogen into the system. Then, it heated to 180 degreeC and continued heating at the temperature for 35 hours, and was made to react.
After completion of the reaction, the reaction mixture was cooled to 70 ° C., 100 mL of toluene was added, and the solid content was separated by filtration. When the residual amount of p-acetotoluidine in the filtrate was quantified by HPLC, the reaction conversion rate was 89%.

[Comparative Example 6C]
In a 200 mL four-necked flask equipped with a stirrer and a thermometer at room temperature, 14.9 g (0.10 mol) of p-acetotoluidine, 25.7 g (0.15 mol) of p-bromotoluene, copper iodide (I ) 1.9 g (0.01 mol) and potassium carbonate (FG-F20 manufactured by Asahi Glass Co., Ltd. was pulverized for 30 minutes in the presence of glass beads with a paint shaker: number average particle size 2 μm) were added successively, and nitrogen was allowed to flow through the system. Stir for minutes. Then, it heated to 180 degreeC, and it was made to react by continuing heating at the temperature for 32 hours.
After completion of the reaction, the reaction mixture was cooled to 70 ° C., 100 mL of toluene was added, and the solid content was separated by filtration. When the residual amount of p-acetotoluidine in the filtrate was quantified by HPLC, the reaction conversion rate was 90%.

[Production of poly (ether sulfone)]
Example 7
In 40 mL of dimethylacetamide, 5.2 g of N, N′-bis (4-hydroxyphenyl) -N, N′-diphenyl-4,4′-biphenyl-diamine and 2.5 g of bis (4-fluorophenyl) sulfone were added. A poly (ether sulfone) was obtained by a condensation reaction at 140 ° C. for 3 hours in the presence of potassium carbonate (FG-F20 manufactured by Asahi Glass: number average particle size 20 μm, specific surface area 0.5 m ² / g) (20 mmol).
The polymer had a weight average molecular weight (Mw) of 3.0 × 10 ⁴ and a number average molecular weight (Mn) of 8.8 × 10 ³ . The molecular weight is measured by GPC in THF (polystyrene standard).

  Using this polymer, a device was produced in the same manner as in Example 8 of JP-A-9-188756, and it was confirmed that it worked effectively as an electroluminescent element.

[Comparative Example 7]
In 40 mL of dimethylacetamide, 5.2 g of N, N′-bis (4-hydroxyphenyl) -N, N′-diphenyl-4,4′-biphenyl-diamine and 2.5 g of bis (4-fluorophenyl) sulfone were added. A poly (ether sulfone) was obtained by condensation reaction at 140 ° C. for 3 hours in the presence of potassium carbonate (special grade manufactured by Kanto Chemical for 10 minutes in a mortar: number average particle size 0.3 mm) (20 mmol) (20 mmol). .
The polymer had a weight average molecular weight (Mw) of 1.5 × 10 ⁴ and a number average molecular weight (Mn) of 6.0 × 10 ³ . The molecular weight is measured by GPC in THF (polystyrene standard).

(Image formation test)
[Example D1]
The surface of a cylinder made of an aluminum alloy having an outer diameter of 30 mm, a length of 351 mm, and a wall thickness of 1.0 mm, which is mirror-finished, is anodized and then sealed with a sealing agent mainly composed of nickel acetate. By performing the treatment, an anodic oxide film of about 6 μm was formed.

  Further, 20 parts of Y-type oxytitanium phthalocyanine and 280 parts of 1,2-dimethoxyethane were mixed as a charge generating substance, and pulverized with a sand grind mill for 2 hours for atomization dispersion treatment. Subsequently, 253 parts of 1,2-dimethoxyethane, polyvinyl butyral (manufactured by Denki Kagaku Kogyo Co., Ltd., trade name “Denkabutyral” # 6000C), and 4-methoxy-4-methyl-2 were added to this micronized processing solution. A dispersion was prepared by mixing a binder solution obtained by dissolving pentanone in 85 parts of a mixture and 230 parts of 1,2-dimethoxyethane.

An anodized aluminum cylinder was dip coated on this dispersion, and a charge generation layer was prepared so that the film thickness after drying was 0.3 μm (bulk density 0.3 g / m ² ).
Next, 60 parts of the compound produced in Example 3 as a charge transport material, 100 parts of a polycarbonate (PC1; viscosity average molecular weight of about 30000) having a structure represented by the following formula (a) as a binder unit as a binder resin, 8 parts of an antioxidant having a structure represented by the formula (b), 0.05 part of silicone oil (trade name: KF96, Shin-Etsu Chemical Co., Ltd.) as a leveling agent, THF / toluene (weight ratio 8 / 2) Photosensitive drum A (photosensitive member) having a laminated type photosensitive layer by dip-coating the liquid dissolved in 640 parts of the mixed solvent on the above-described charge generation layer so that the film thickness after drying becomes 18 μm. Got.

  The produced photoreceptor drum A is mounted on an electrophotographic characteristic evaluation apparatus (basic and applied electrophotographic technology, edited by the Electrophotographic Society, Corona, pages 404 to 405) prepared according to the standard of the Electrophotographic Society. The electrical characteristics were evaluated by the charging (minus polarity), exposure, potential measurement, and static elimination cycle.

Irradiation energy (half-exposure exposure) when the surface potential becomes -350 V by charging the photosensitive member so that the initial surface potential is -700 V and irradiating the light of the halogen lamp with a monochromatic light of 780 nm with an interference filter. Energy) was measured as sensitivity (E1 / 2) (μJ / cm ² ). Further, the post-exposure surface potential (VL1) after 100 ms when the exposure light was irradiated at an intensity of 1.0 μJ / cm ² was measured (−V).

Furthermore, a positive polarity corotron charger was installed for the purpose of simulating the transfer between the potential measurement and the charge removal in the above process. The drum was rotated at a speed of 1 cycle / s, the static elimination light was turned off, and the negative and positive charging cycles were repeated 4000 times. Thereafter, the static elimination light was turned on again, and the post-exposure surface potential (VL2) was measured in the same manner as VL1 (−V). Here, negative charging was performed under the condition that the initial surface potential was charged to −700 V with a scorotron, and positive charging was performed with corotron charging at a constant output of 7 kV.
By measuring ΔVL = VL2−VL1, the magnitude of the influence of repeated positive charging on the electrophotographic photoreceptor characteristics was evaluated. The results are shown in Table 8.

  Further, the electrophotographic photosensitive member A was mounted on a cyan drum cartridge of a commercially available tandem type color printer (Microline 3050c manufactured by Oki Data Co., Ltd.) compatible with A3 printing, and mounted on the printer. First, under the conditions of a temperature of 35 ° C. and a humidity of 80%, the printing media type was set to OHP, and 100 sheets of cyan images were printed on the A4 version OHP film MC502 manufactured by Mitsubishi Chemical Media Corporation by vertical feeding. Next, a solid cyan image was printed on A3 paper, and image evaluation was performed. OHP passage area for solid images printed on A3 paper (the part where the photoconductor is damaged by transfer through the OHP sheet) and non-passage area for OHP (the part where the photoconductor is damaged by direct transfer) When the density difference was confirmed, the density difference was only slightly confirmed visually.

[Comparative Example D1]
In Example D1, electrical characteristics and image characteristics were evaluated in the same manner as in Example D1, except that the compound produced in Comparative Example 3A was used instead of the charge transport agent used. The results of electrical characteristics are shown in Table 1.
In the image characteristics, the OHP passing area of the solid image printed on the A3 paper (the portion where the photoconductor was damaged by the transfer through the OHP sheet) and the non-OHP passing area (the photoconductor was damaged by the direct transfer). When the density difference of the received part) was confirmed, the density difference was clearly recognized visually.

[Summary]
From the result of said Example and comparative example, according to the manufacturing method of the organic compound of this invention, it was confirmed that an organic compound can be manufactured with high yield and high purity using carbonate.
In addition, when an organic compound obtained by the method for producing an organic compound of the present invention is used as an electronic material, and the electrophotographic photoreceptor and the image forming apparatus are configured using the electronic material, an electrophotographic photoreceptor having high performance. In addition, it was confirmed that an image forming apparatus can be obtained.

  The present invention can be used in any industrial field, and is particularly suitable for an industrial field in which an image forming apparatus is used.

1 is a schematic diagram illustrating a main configuration of an embodiment of an image forming apparatus of the present invention.

Explanation of symbols

1 Electrophotographic photoreceptor 2 Charging device (charging roller)
DESCRIPTION OF SYMBOLS 3 Exposure apparatus 4 Developing apparatus 5 Transfer apparatus 6 Cleaning apparatus 7 Fixing apparatus 41 Developing tank 42 Agitator 43 Supply roller 44 Developing roller 45 Control member 71 Upper fixing member (fixing roller)
72 Lower fixing member (fixing roller)
73 Heating device T Toner P Recording paper

Claims (12)

An organic compound production method for producing an organic compound by reacting a raw material,
A method for producing an organic compound, wherein a carbonate having a number average particle diameter of 60 μm or less and 5 μm or more is present in the reaction system of the reaction. The method for producing an organic compound according to claim 1, wherein the carbonate is a potassium salt. 3. The production of the organic compound according to claim 1, wherein at least one selected from the group consisting of an amine compound, an aryl compound, an ether compound, an alkene compound, and an ester compound is produced as the organic compound. Method. The specific surface area of the said carbonate is 0.5 m < ² > / g or more, The manufacturing method of the organic compound as described in any one of Claims 1-3 characterized by the above-mentioned. The method for producing an organic compound according to any one of claims 1 to 4, wherein the carbonate has a bulk density of 0.25 g / mL or more and 1.1 g / mL or less. The reaction temperature of the said reaction is -10 degreeC or more and 250 degrees C or less, The manufacturing method of the organic compound as described in any one of Claims 1-5 characterized by the above-mentioned. The method for producing an organic compound according to claim 1, wherein a reaction solvent having a relative dielectric constant of 2 or more and 50 or less is used in the reaction. An electronic material produced by the method for producing an organic compound according to claim 1. An electronic device using the electronic material according to claim 8. An electrophotographic photosensitive member having a photosensitive layer on a conductive support,
An electrophotographic photosensitive member comprising the electronic material according to claim 8 in the photosensitive layer. The electrophotographic photosensitive member according to claim 10,
A charging unit for charging the electrophotographic photosensitive member;
Exposing the charged electrophotographic photoreceptor to form an electrostatic latent image; and
An image forming apparatus comprising: a developing unit that develops an electrostatic latent image formed on the electrophotographic photosensitive member. The electrophotographic photosensitive member according to claim 10,
A charging unit for charging the electrophotographic photosensitive member, an exposure unit for exposing the charged electrophotographic photosensitive member to form an electrostatic latent image, and developing the electrostatic latent image formed on the electrophotographic photosensitive member An electrophotographic photosensitive member cartridge comprising at least one of the developing units.

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