JP4164007B2 - Method for producing material for electrophotographic photosensitive member, material for electrophotographic photosensitive member, and electrophotographic photosensitive member using the same - Google Patents

Description

  The present invention relates to a material used for an electrophotographic photoreceptor, a manufacturing method thereof, and an electrophotographic photoreceptor using the material.

  In order to stabilize the electrical characteristics of the electrophotographic photosensitive member, high purity is required for main materials such as a charge transport material and a binder resin used in the photosensitive layer. In order to satisfy these requirements, a method for refining a crude product is usually essential when preparing these materials. For purification, there are methods such as sublimation, recrystallization, reprecipitation, and solvent washing. As an industrially used method for electrophotographic photosensitive material, adsorbent treatment is known.

  For example, as a method of purifying a crude product of a charge transport material using an adsorbent, a method of combining activated clay and activated carbon (for example, refer to Patent Document 1), a method of further purification with activated silica after purification with activated clay (for example, Patent Document 2), a method of improving purification efficiency by repeating the treatment operation twice or more using the same adsorbent (see Patent Document 3, for example), and electronic product materials are activated under high temperature conditions of 65 ° C. or higher Techniques such as a method of refining by contacting with clay (see, for example, Patent Document 4) are disclosed. In addition, it has been proposed to stabilize the electric characteristics of the electrophotographic photosensitive member by purifying the binder resin using activated clay (see, for example, Patent Document 5).

  As a material for the photosensitive layer of the electrophotographic photoreceptor, various trace components are used in addition to main materials such as a charge transport material and a binder resin. However, even if these trace components are used as is without purifying the crude product, the amount of impurities mixed in the photosensitive layer is small, and it is considered that the influence on the characteristics of the photoreceptor is extremely small. It was. Therefore, from the viewpoint of efficiency and cost reduction, these trace components are usually used as they are without purifying the crude product.

JP 60-233156 A Japanese Patent Laid-Open No. 4-310962 JP-A-7-56365 JP 2002-14478 A Japanese Patent Laid-Open No. 2001-13698

  However, although the characteristics of the photoreceptor are certainly improved by refining the charge transport material, the binder resin, etc., they are not sufficient yet, and there remains room for further improvement. In particular, under the recent demand for higher resolution, there has been a demand for an electrophotographic photosensitive member having a smaller residual potential and higher sensitivity, that is, more excellent characteristics.

  The present invention has been made in view of the above-described problems, and an object of the present invention is to provide an electrophotographic photoreceptor material capable of realizing an electrophotographic photoreceptor having a small residual potential and high sensitivity, that is, excellent characteristics, and a method for producing the same. And providing an electrophotographic photosensitive member using the material.

  As a result of intensive studies in view of the above problems, the present invention has focused on a compound having a specific structure, which is mainly used for reducing the surface energy of the photoreceptor among components other than the charge transport material and the binder resin. The inventors have found that the electrical properties of the photoreceptor are remarkably improved by using the crude product containing the compound as a photoreceptor material after contacting the adsorbent with the adsorbent, and have reached the present invention.

That is, the gist of the present invention resides in the following [1] to [ 6 ].
[1]. In an electrophotographic photosensitive member formed by forming a photosensitive layer having a layer containing at least a binder resin on a conductive support, it is contained in the layer in a range of 30 parts by weight or less with respect to 100 parts by weight of the binder resin. A method for producing an electrophotographic photoreceptor material, wherein a crude product containing a compound represented by the following general formula (1) and / or a compound represented by the following general formula (2) is brought into contact with an adsorbent. A method for producing a material for an electrophotographic photosensitive member.
(In the general formula (1), A represents a linear or branched, saturated or unsaturated aliphatic hydrocarbon group having 20 to 500 carbon atoms. X represents a divalent linking group. B represents an aromatic hydrocarbon group which may have a substituent having a formula weight of 500 or less, or a hydrogen atom, and n represents an integer of 1 to 5.)
(In the general formula (2), C represents an optionally substituted hydrocarbon group having a formula weight of 2000 or less and having 2 or more aromatic rings. Y represents a divalent linking group. (It represents a linear or branched, saturated or unsaturated aliphatic hydrocarbon group having 10 to 500 carbon atoms, and m represents an integer of 1 to 10.)
[2]. The method for producing a material for an electrophotographic photosensitive member according to [1], wherein C in the general formula (2) has a structure represented by the following formula (3).
(In Formula (3), R ¹ represents a hydrogen atom, a halogen atom, a substituted or unsubstituted aliphatic hydrocarbon group, a substituted or unsubstituted aromatic hydrocarbon group, Z represents a bonding group, and q represents Represents an integer of 1 to 10, and p represents an integer of 0 to 4.)
[ 3 ]. In a state where the the crude was dissolved in boiling 40 ° C. or more organic solvents, wherein the contacting with the adsorbent, the manufacturing method of the electrophotographic photoreceptor material [1] or [2].
[ 4 ]. [1] A material for an electrophotographic photosensitive member produced by the method for producing a material for an electrophotographic photosensitive member according to [3] .
[ 5 ]. In the electrophotographic photosensitive member having a photosensitive layer having a layer containing at least a binder resin on a conductive support, the material for electrophotographic photosensitive member of [ 4 ] in the layer is 30 parts by weight with respect to 100 parts by weight of the binder resin. An electrophotographic photosensitive member, which is contained in an amount of at most parts by weight .
[6]. 100 weight of the binder resin obtained by bringing the binder resin, the compound represented by the general formula (1) and / or the crude product containing the compound represented by the general formula (2) into contact with an adsorbent A method for producing an electrophotographic photosensitive member, comprising forming a photosensitive layer having a layer containing 30 parts by weight or less of the material for an electrophotographic photosensitive member with respect to parts on a conductive support.

  According to the present invention, a crude product containing a compound having a specific structure used mainly for reducing the surface energy of a photoreceptor is used as a material for an electrophotographic photoreceptor after being brought into contact with an adsorbent. An electrophotographic photoreceptor having a small residual potential and high sensitivity, that is, having excellent characteristics is realized.

  Hereinafter, embodiments of the present invention will be described, but the present invention is not limited to the following descriptions, and various modifications can be made within the scope of the gist of the present invention.

[1. Electrophotographic photosensitive material]
The material for an electrophotographic photoreceptor of the present invention (hereinafter abbreviated as “the material of the present invention” as appropriate) is produced by bringing a crude product containing a compound having a specific structure into contact with an adsorbent. .

<Active ingredient compounds>
In the production of the material of the present invention, as a raw material, a compound represented by the following general formula (1) and / or a compound represented by the following general formula (2) (hereinafter, these compounds are collectively referred to as appropriate) A crude product containing “active compound” is used. These active ingredient compounds are mainly used in electrophotographic photoreceptors for the purpose of lowering the surface energy of the photoreceptor, and the present inventors have applied Japanese Patent Application Nos. 2002-055861 and 2003-102211. These compounds point out their effectiveness in each specification.

  In general formula (1), A represents a linear or branched, saturated or unsaturated aliphatic hydrocarbon group. The degree of branching and unsaturation of the fatty chain is not particularly limited, but it is preferably not so much, particularly preferably completely saturated. The carbon number of A is usually 20 or more, preferably 30 or more, more preferably 40 or more, and usually 500 or less, preferably 300 or less.

X represents a divalent linking group. The type is not particularly limited, but those having 6 or less atoms are preferable. Specific examples include ether groups (divalent oxygen atom groups), thioether groups (divalent sulfur atom groups), sulfonyl groups, sulfone groups, salphenyl groups, carbonyl groups, ester groups, thioester groups, and divalent phosphorus. Examples include an acid ester group, a methylene group, and an ethylene group. Among these, an ether group (—O—), a thioether group (—S—), a methylene group (—CH ₂ —), or a carbonyl group (—C (═O) —) is preferable from the viewpoint of ease of synthesis. .

  B represents a monovalent aromatic hydrocarbon group or a hydrogen atom. Specific examples of the monovalent aromatic hydrocarbon group include a phenyl group, a naphthyl group, an anthryl group, and a phenanthryl group. The aromatic hydrocarbon group may further have a substituent. Specific examples of the substituent include alkyl groups such as methyl group, ethyl group, butyl group, hexyl group and undecane group; alkenyl groups such as allyl group and isopropenyl group; aryl groups such as phenyl group and naphthyl group; methoxy group Alkoxy group such as ethoxy group, propoxy group; phenoxy group; arylalkoxy group such as benzyloxy group and phenethyloxy group; halogen atom such as chloro atom and bromo atom; hydroxy group; acyl group; benzoyl group; Dialkylamino groups such as amino group and diethylamino group; arylalkylamino groups such as dibenzylamino group and benzyl-ethylamino; diarylamino groups such as diphenylamino group and di-p-tolylamino group; chloromethyl group and bromopropyl group Haloalkyl groups such as It is. Among these, as a substituent, a phenyl group or a diarylamino group is preferable. When B is an aromatic hydrocarbon group, the formula weight, if it has a substituent, is the value of the entire B including the substituent, usually 500 or less, preferably 400 or less, more preferably 300 or less. .

  n represents an integer of 1 to 5. Especially, the integer of 1-4 is preferable and the integer of 1-3 is more preferable. When n is 2 or more, the plurality of Xs and the plurality of Bs may be the same or different from each other.

In general formula (2), C represents an optionally substituted hydrocarbon group having two or more aromatic rings. If the formula amount of C is large, the affinity with the photosensitive layer component is improved, which is advantageous. However, if it is too large, the effect of lowering the surface energy becomes relatively small, and the use necessary to obtain a sufficient effect. The amount of the formula C is disadvantageous because the amount is increased, and when it has a substituent, the formula amount of C is generally 2000 or less, preferably 1500 or less, in terms of the value of the entire hydrocarbon group including the substituent. Preferably it is 1000 or less, and is 125 or more normally, Preferably it is 150 or more, More preferably, it is the range of 200 or more.

Preferable examples of C include a group having a structure represented by the following formula (3).

In formula (3), q represents an integer of 1 to 10. Z is a linking group and takes a valence corresponding to the number of q. For q = 1, Z is not present, comprises one or more aromatic rings in any of the R ^1. When q is 2 or more, the plurality of R ¹ and the plurality of p may be the same as or different from each other. R ¹ represents a hydrogen atom, a halogen atom, a substituted or unsubstituted aliphatic hydrocarbon group, or a substituted or unsubstituted aromatic hydrocarbon group. p represents an integer of 0 to 4. When p is 2 or more, the plurality of R ¹ may be the same as or different from each other. Further, a plurality of R ¹ may be bonded to each other to form a ring structure. As Z, for example, an alkylene group such as a methylene group, an ethylene group, or a propylene group; an arylene group such as a phenylene group or a naphthalene group, or a combination thereof can be used. These may have a substituent, and an ether group, a thioether group, a sulfonyl group, a sulfone group, a salphenyl group, a carbonyl group, an ester group, a carbonate ester group, a thioester group, a phosphate ester group, etc. in Z You may have. Moreover, Z does not exist and aromatic rings may couple | bond together directly.

In addition, the hydrocarbon group of C in the general formula (2) may have, or the aliphatic hydrocarbon group / aromatic hydrocarbon group of R ¹ in the formula (3) may have. The substituent is not particularly limited as long as it does not fall within the spirit of the present invention. Specific examples of the substituent include alkyl groups such as methyl group, ethyl group, butyl group, hexyl group and undecane group; alkenyl groups such as allyl group and isopropenyl group; aryl groups such as phenyl group and naphthyl group; methoxy group Alkoxy group such as ethoxy group, propoxy group; phenoxy group; arylalkoxy group such as benzyloxy group and phenethyloxy group; halogen atom such as chloro atom and bromo atom; hydroxy group; acyl group; benzoyl group; Dialkylamino groups such as amino group and diethylamino group; arylalkylamino groups such as dibenzylamino group and benzyl-ethylamino; diarylamino groups such as diphenylamino group and di-p-tolylamino group; chloromethyl group and bromopropyl group Haloalkyl groups such as It is.

  In general formula (2), Y represents a divalent linking group. The type is not particularly limited, but those having 6 or less atoms are preferable. Specific examples include ether groups (divalent oxygen atom groups), thioether groups (divalent sulfur atom groups), sulfonyl groups, sulfone groups, salphenyl groups, carbonyl groups, ester groups, thioester groups, and divalent phosphorus. Examples include an acid ester group, a methylene group, and an ethylene group. Among these, an ether group (—O—) or an ester group (—COO—) is preferable from the viewpoint of ease of synthesis. Although the ester group (—COO—) is asymmetrical, it may be in any direction as will be described later. Which orientation is preferred depends on the type of compound and the ease of synthesis. Y is preferably bonded to the aromatic ring portion of C, but it is preferable that two or more Y are not bonded simultaneously to one aromatic ring of C.

  D represents a linear or branched, saturated or unsaturated aliphatic hydrocarbon group. The degree of branching of the fatty chain is not particularly limited, but is preferably not so much in order to effectively reduce the surface energy. Specifically, it is preferable that the number of branches is 3 or less, and it is particularly preferable that the branched chain is a straight chain having no branches or a branched chain having 1 branch. Unsaturated bonds can be present but are preferably all saturated. As for the carbon number of D, the compatibility with the photosensitive layer tends to be improved when the carbon number is small, while the effect of lowering the surface energy tends to be slightly smaller, and conversely when the carbon number is large. While the surface energy reduction effect tends to increase, the compatibility with the photosensitive layer and the stability and compatibility of the coating solution when forming the photosensitive layer tend to deteriorate. Specifically, the carbon number of D is usually 10 or more, preferably 18 or more, more preferably 23 or more, and usually 500 or less, preferably 100 or less, and more preferably 50 or less.

  m represents an integer of 1 to 10. Especially, the integer of 2-10 is preferable and the integer of 2-4 is still more preferable. When m is 2 or more, the plurality of Y and the plurality of D may all be the same or different from each other.

  X in the general formula (1) and Y in the general formula (2) are left-right asymmetric groups such as ester groups, thioester groups, and divalent phosphate ester groups (hereinafter referred to as “ester groups and the like”). In the case, the difference in right and left direction of the ester group etc. in the general formula (1) and the general formula (2), that is, A (or C) is bonded to either of the ester groups, etc., and B (or D) is bonded to which Depending on the type, the types of the compounds of the general formula (1) and the general formula (2) are different. In the present invention, any compound that satisfies the general formula (1) or the general formula (2) can be used as the active ingredient compound regardless of the right and left directions of the ester group and the like.

  Preferable examples of the compound represented by the general formula (1) include compounds shown in the following Tables 1 to 3. Of course, the compound of General formula (1) is not limited to these compounds. Moreover, in Tables 1-3, only the part corresponding to A, X, B of the compound shown by General formula (1) was described.

  Preferable examples of the compound represented by the general formula (2) include compounds shown in the following Tables 4 to 8. Of course, the compound of General formula (2) is not limited to these compounds. Moreover, in Tables 4-8, only the part corresponded to C, Y, D of the compound shown by General formula (2) was described. Among Y in Tables 4 to 8, the left and right orientations of the ester groups are different, but C is bonded to the left side and D is bonded to the right side with respect to the ester groups arranged as shown in the table.

  When these active ingredient compounds are contained in the photosensitive layer of the electrophotographic photoreceptor, any one of them may be contained alone, or two or more thereof may be contained in any combination. In addition, when two or more active ingredient compounds are contained, only two or more compounds belonging to any one of the general formula (1) and the general formula (2) may be contained and belong to the general formula (1). You may contain together 1 type, or 2 or more types of compounds, and 1 type or 2 or more types of compounds which belong to General formula (2).

  The above-mentioned active ingredient compound is, for example, an ester of an aromatic carboxylic acid and an aliphatic alcohol that reacts an aromatic compound having a phenolic hydroxyl group with a partially brominated aliphatic compound under alkaline conditions. It is possible to synthesize by a technique such as By such a synthesis method, a crude product containing the above-mentioned active ingredient compound is actually obtained.

<Significance of contacting crude product with adsorbent>
When the active ingredient compound is used for the photoreceptor, the preferred amount is relatively small as described later. Specifically, taking the charge transporting layer of a normal laminated type photoreceptor as an example, the main components are a charge transporting material and a binder resin, and the active component compound is contained as one of the other minor components. Become.

  Conventionally, charge transport materials and binder resins, which are the main components, have been refined, but other trace components have little effect on improving photoreceptor characteristics compared to the time and cost of purification. From the viewpoint of efficiency and cost reduction, it is customary to use the crude product as it is without purification.

  On the other hand, the present invention is characterized in that the crude product containing the above-mentioned active ingredient compound is used as a material for an electrophotographic photosensitive member after it is brought into contact with an adsorbent. As a result, a remarkable improvement effect of the photoreceptor characteristics that cannot be expected from the viewpoint of purification of a trace component is realized.

  The reason why the characteristics of the photoreceptor are remarkably improved by using the material brought into contact with the adsorbent is not certain, but some change occurs in the material due to the contact treatment with the adsorbent, resulting in the electrical characteristics of the photoreceptor. This is considered to be because a material with less influence is realized. Although it is unclear what kind of change will occur specifically, for example, among the components contained in the crude product, a component that has a particularly adverse effect on the electrical characteristics of the electrophotographic photoreceptor, for example, a source of residual potential It is conceivable that impurities and the like are efficiently removed by the adsorbent and the material is effectively purified, and that these components are detoxified by the adsorbent. In addition, as an impurity which becomes a generation source of a residual potential, alcohol, amines, etc. which were mixed at the time of manufacture of the crude product of an active ingredient compound can be considered.

<Method of contacting with adsorbent>
The method for bringing the crude product into contact with the adsorbent is not particularly limited, and various methods can be used, but the following method is preferably used from the viewpoint of operability and the like. First, a crude product containing the above-mentioned active ingredient compound is dissolved in an organic solvent. This solution and an adsorbent described later are mixed and usually stirred for several seconds or more, preferably 10 minutes or more, and then the adsorbent is separated by filtration. In this case, the adsorbent may be added and mixed in a container containing the crude product solution, or the crude product solution may be poured and mixed into the container containing the adsorbent. Moreover, the whole quantity may be contacted at once, and it may be divided and contacted several times. The adsorbent may be used in a dry state, but may be used after the adsorbent is moistened with an organic solvent in order to prevent dust scattering. Alternatively, in consideration of operability, it is also possible to use a technique of filling a pipe, a column, a filtration device or the like with an adsorbent and pouring a solution in which a crude product is dissolved.

  The solvent for dissolving the crude product is not particularly limited as long as it can dissolve the crude product, but an aliphatic hydrocarbon solvent or an aromatic hydrocarbon solvent is preferable. Preferable specific examples include aromatic hydrocarbon solvents such as benzene, toluene, o-xylene, m-xylene, p-xylene, o-cymene, m-cymene, p-cymene, mesitylene, anisole, ethylxylene, ethyl. Toluene, ethylanisole, methylnaphthalene, diphenylmethane and the like, and aliphatic hydrocarbon solvents include n-hexane, n-heptane, n-octane, n-decane, n-dodecane, 2,3-dimethylhexane, Examples include 2-methylheptane, 2-methylhexane, 3-methylhexane, and cyclohexane. The said solvent may be used as a single solvent, and may be used as a mixed solvent by mixing with arbitrary combinations.

  The temperature at the time of performing the contact treatment with the adsorbent is not particularly limited as long as it is not higher than the boiling point of the solvent to be used and not lower than the freezing point, and may be appropriately selected according to the type of the solvent to be used. In this case, it is preferable to treat at a relatively low temperature. Generally, it is usually 80 ° C. or lower, preferably 60 ° C. or lower, and usually 0 ° C. or higher, preferably 5 ° C. or higher, more preferably 10 ° C. or higher.

  If the amount of the adsorbent is too large, a decrease in purification yield due to poor filterability or the like can be considered. Therefore, the value of (adsorbent weight) / (crude product weight) is preferably 1 or less, more preferably 0. .5 or less. On the other hand, if the amount is too small, the purification efficiency decreases, so it is usually 0.01 or more, preferably 0.05 or more.

<Adsorbent>
The adsorbent used in the production of the material of the present invention is not particularly limited, but representative examples include silica gel, alumina, montmorillonite, activated clay, activated carbon and the like. Among these, activated clay and activated carbon are preferable. The reason for this is that activated clay is particularly excellent in detoxifying components that adversely affect the electrical properties of the electrophotographic photoreceptor, and activated carbon is a porous particle that is particularly useful in the purification of impurities. It is because it demonstrates excellent ability.

  As the activity of the adsorbent, if the activity is too high, the adverse effect on the substance to be purified will increase, while if the activity is too low, the purification efficiency will decrease. is there. Examples of such adsorbents include activated alumina, activated silica gel, acidic clay, activated clay, activated carbon, and the like, but from the viewpoint of production cost, activated carbon or activated clay is preferable, and the efficiency of contact treatment and operability during production. In view of this aspect, activated clay is more preferable than activated carbon. Examples of the activated carbon include those obtained by treating palm husk, charcoal, lignite, peat, and the like with a chemical packing method, and those treated with an activating material such as zinc chloride and steam are particularly preferable. The activated clay is obtained by adding various activation treatments to raw clay minerals such as acid clay, and as the activation treatment, treatments using various acids are usually performed. The type of acid used for the activation treatment is not particularly limited, but from the viewpoint of treatment effect and cost, treatment with an inorganic acid is preferred, and treatment with sulfuric acid or the like is particularly preferred.

  In addition, if these adsorbents remove excessive water, the activity of the adsorbent becomes too high and adversely affects the substance to be purified. Therefore, the water content of the adsorbent is usually 3% by weight. Above, more preferably 5% by weight or more. On the other hand, if the water content is too high, the activity of the adsorbent decreases, so the water content of the adsorbent is usually 15% by weight or less, and preferably 12% by weight or less from the viewpoint of increasing purification efficiency.

The surface area of the adsorbent is preferably larger from the viewpoint of increasing the adsorption capacity, and is usually 50 m ² / g or more, preferably 100 m ² / g or more, more preferably 150 m ² / g or more. The upper limit is not particularly limited, but is usually 400 m ² / g or less.

  The shape of the adsorbent is not particularly limited, but is preferably granular when handling properties at the time of manufacture are taken into consideration. The particle size is usually in the range of 5 mesh or more and 500 mesh or less in consideration of filterability at the time of production. Among these, considering the filtration performance, 5 mesh or more and 30 mesh or less are preferable, and considering the adsorption efficiency, 50 mesh or more and 500 mesh or less are preferable.

  The particle size of the above adsorbent is defined as follows. That is, when a screening test specified in JIS Z 8815 (General Rules for Screening Tests) is performed using a test sieve specified in JIS Z 8801 (test sieves), the following formula (1) and Of the sieves having a cumulative sieve lower percentage Q (%) defined by the formula (2) of 85% or more, the sieve opening value (mesh) having the smallest opening is used as the particle size of the adsorbent. .

[Equation 1]
R = (m / T) × 100 (1)
Where R: percentage on the sieve (%), m: mass (g) of the sample (adsorbent) on the sieve, and T: mass (g) of the recovered sample (adsorbent).
[Equation 2]
Q = 100−ΣR (2)
However, ΣR represents the percentage (%) on the total sieve.

  The average diameter of the adsorption holes of the adsorbent is usually in the range of 10 angstroms or more, preferably 10 angstroms or more, and usually 100 angstroms or less, preferably 70 angstroms or less.

[2. Electrophotographic photoreceptor]
The electrophotographic photoreceptor of the present invention is characterized by having a photosensitive layer on a conductive support and containing the above-described material of the present invention in the photosensitive layer.

<Support>
As the conductive support, for example, a drum made of a metal material such as aluminum, aluminum alloy, stainless steel, copper, or nickel, and a conductive layer such as aluminum, copper, palladium, tin oxide, or indium oxide is provided on the surface. In addition, an insulating support such as a polyester film, paper, or the like formed into a sheet, belt, drum, or roll, or a material obtained by kneading conductive fine particles such as carbon or copper powder in plastic or paper is used.

In the case of using an aluminum drum, the material used is, for example, an extruded or drawn tube of aluminum alloy such as 3000 series, 5000 series, 6000 series, etc., which is regulated by JIS, or a machined product thereof. The maximum surface roughness R _max is preferably 2.5 μm or less.

  A known blocking layer, which is usually used, may be provided between the conductive support and the photosensitive layer. Examples of the blocking layer include inorganic layers such as aluminum anodized film, aluminum oxide and aluminum hydroxide, organic layers such as polyvinyl alcohol, casein, polyvinyl pyrrolidone, polyacrylic acid, celluloses, gelatin, starch, polyurethane, polyimide and polyamide. Is used.

  In the case of using an aluminum anodic oxide coating, the film thickness is preferably in the range of usually 1 μm or more and 10 μm or less, for example. In order to enhance the blocking function, it is desirable to be sealed with nickel acetate or the like.

  When the organic layer is used as a barrier layer, a metal oxide such as titania, alumina, silica and zirconium oxide, or a metal fine powder such as copper, silver and aluminum may be used alone or mixed and dispersed. The particle size of these fine powders can be selected as appropriate. For example, it is preferable to use a primary particle size of several tens of nm to several μm, and they may be used in combination.

  The film thickness of these barrier layers can be appropriately set, but it is usually 0.05 μm or more, preferably 0.1 μm or more, and usually 20 μm or less, preferably 10 μm or less.

<Photosensitive layer>
The type of the photosensitive layer formed on the conductive support includes a single layer type in which the charge generation material and the charge transport material are present in the same layer and dispersed in the binder resin, and the charge generation material in the binder resin. The charge generation layer and the charge transport layer in which the charge transport material is dispersed in a binder resin may be used.

  In addition, as the laminated photosensitive layer, a charge generation 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, but a forward laminated type photosensitive layer capable of exhibiting the most balanced photoconductivity is preferable.

  Furthermore, as the outermost surface layer, various conventionally known functional layers such as an overcoat layer mainly composed of a thermoplastic or thermosetting polymer may be provided.

<Charge generation layer>
In the case of a laminated photosensitive layer, examples of the charge generation material used in the charge generation layer include azo pigments, phthalocyanine pigments, perylene pigments, quinacridone pigments, polycyclic quinone pigments, indigo pigments, benzimidazole pigments, pyrylium salts, thiapyrylium salts, Examples include squalium salt.

  For the charge generation layer, these charge generation materials are, for example, polyester resin, polyvinyl acetate, polyacrylate ester, polymethacrylate ester, polyester, polycarbonate, polyvinyl acetoacetal, polyvinyl propional, polyvinyl butyral, phenoxy resin, epoxy resin. In addition, it is used in the form of a dispersion layer bound with various binder resins such as urethane resin, cellulose ester, and cellulose ether. In this case, the charge generation material is used in a range of usually 30 to 500 parts by weight with respect to 100 parts by weight of the binder resin. The film thickness of the charge generation layer is usually 0.1 μm or more, preferably 0.15 μm or more, and usually 2 μm or less, preferably 0.8 μm or less.

  In addition, the charge generation layer may contain various components such as a leveling agent, an antioxidant, and a sensitizer for improving coating properties, as necessary. Further, it may be formed as a vapor-deposited film of a charge generation material.

<Charge transport layer>
The charge transport layer may be formed of a binder resin having a charge transport function alone, but a structure in which a charge transport material is dispersed in the binder resin is more desirable.
Examples of the binder resin used in the charge transport layer include vinyl polymers such as polymethyl methacrylate, polystyrene, and polyvinyl chloride, and copolymers thereof, polycarbonate, polyester, polyester carbonate, polysulfone, polyimide, phenoxy, epoxy, and silicon. Resin etc. are mentioned. These partially crosslinked cured products can also be used.

  Examples of the charge transport material include polycyclic aromatic compounds such as pyrene and anthracene, heterocyclic compounds such as carbazole, indole, oxazole, thiazole, pyrazoline, oxathiazole, thiadiazole, and triazole, p-diethylaminobenzaldehyde-N, N-diphenyl Hydrazone compounds such as hydrazone, N-methylcarbazole-3-carbaldehyde-N, N-diphenylhydrazone, and 5- (4- (di-p-tolylamino) benzylidene) -5H-dibenzo (a, d) cycloheptene. Styryl compounds, triarylamine compounds such as p-tolyltolylamine, benzidine compounds such as N, N, N, N-tetraphenylbenzidine, butadiene compounds, and tris such as di- (p-ditolylaminophenyl) methane Phenylmethane Such compounds.

  The ratio of the binder resin to these charge transport materials is usually 30 parts by weight or more, preferably 40 parts by weight or more, and usually 200 parts by weight or less, preferably 150 parts by weight or less, based on 100 parts by weight of the binder resin. Used in range.

  In addition, the charge transport layer may contain various additives such as antioxidants such as hindered phenols and hindered amines, ultraviolet absorbers, sensitizers, leveling agents, and electron withdrawing substances as necessary. The thickness of the charge transport layer is usually 10 μm or more, and usually 60 μm or less, preferably 45 μm or less.

<Single layer type photosensitive layer>
When the photosensitive member has a single-layer type photosensitive layer, the charge generation material is dispersed in a matrix mainly composed of the binder resin and the charge transport material having the above-described mixing ratio. In this case, the particle diameter needs to be sufficiently small, and is preferably 1 μm or less, more preferably 0.5 μm or less.

  If the amount of the charge generating material dispersed in the photosensitive layer is too small, sufficient sensitivity cannot be obtained, and if it is too large, there are adverse effects such as a decrease in chargeability and a decrease in sensitivity. % Or more, more preferably 10% by weight or more, preferably 50% by weight or less, more preferably 45% by weight or less. The film thickness of the photosensitive layer is usually in the range of 5 μm or more, preferably 10 μm or more, and usually 50 μm or less, preferably 45 μm or less.

  Also in the case of a single-layer type photosensitive layer, a known plasticizer for improving film formability, flexibility, mechanical strength, etc., an inhibitor for suppressing residual potential, and an improvement in dispersion stability. A dispersion aid, a leveling agent for improving coating properties, a surfactant, silicone oil, fluorine oil and other components may be contained.

<Layer formation method>
Each layer of the photoreceptor is formed by sequentially applying and forming a coating solution obtained by dissolving or dispersing a substance contained in the layer in a solvent using a known method such as a dip coating method, a spray coating method, or a ring coating method. Is done.

<Contains electrophotographic photosensitive material>
The material of the present invention is contained in the photosensitive layer of the electrophotographic photoreceptor, and specifically, it is preferably used for the outermost surface layer. The outermost surface layer varies depending on the layer type of the photosensitive layer, but the photosensitive layer is a single layer type photoconductor, the charge transport layer is a normal layer type photoconductor, and the charge layer is a reverse layer type photoconductor. In the case of a photoreceptor having a generation layer and an overcoat layer, the overcoat layer is indicated. Of course, it may be contained not only in the outermost surface layer but also in one or more other layers.

  The amount of the material of the present invention varies depending on the layer type of the photosensitive layer and the layer to be contained, but when it is contained in the charge transporting layer of the forward lamination type photosensitive layer, it is based on 100 parts by weight of the binder resin of the charge transporting layer. Usually 0.01 parts by weight or more, preferably 0.1 parts by weight or more, more preferably 0.3 parts by weight or more, and usually 30 parts by weight or less, preferably 20 parts by weight or less, more preferably 20 parts by weight. Use within the following range. Also when contained in the photosensitive layer of the dispersion type photosensitive layer, it is used in the same ratio with respect to the binder resin of the photosensitive layer. On the other hand, in a photoreceptor having an overcoat layer, when it is contained in the overcoat layer, it is usually used in a range of 0.1 to 50 parts by weight with respect to 100 parts by weight of the resin component of the overcoat layer. Is preferred.

[3. Image forming apparatus]
Next, an embodiment of an image forming apparatus using the electrophotographic photosensitive member 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 2, an exposure device 3, and a developing device 4, and further, a transfer device 5, a cleaning device 6 and a fixing device as necessary. A device 7 is provided.

  The electrophotographic photoreceptor 1 is not particularly limited as long as it is the above-described electrophotographic photoreceptor of the present invention, but in FIG. 1, as an example, a drum in which the above-described photosensitive layer is formed on the surface of a cylindrical conductive support. The photoconductor is shown. A charging device 2, an exposure device 3, a developing device 4, a transfer device 5, and a cleaning device 6 are disposed along the outer peripheral surface of the electrophotographic photosensitive member 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. In FIG. 1, a roller-type charging device (charging roller) is shown as an example of the charging device 2, but other corona charging devices such as corotron and scorotron, and contact-type charging devices such as charging brushes are often used.

  In many cases, the electrophotographic photosensitive member 1 and the charging device 2 are designed to be removable from the main body of the image forming apparatus as a cartridge including both of them (hereinafter, appropriately referred to as a photosensitive cartridge). For example, when the electrophotographic photoreceptor 1 or the charging device 2 deteriorates, the photoreceptor cartridge can be removed from the image forming apparatus main body, and another new photosensitive cartridge can be mounted on the image forming apparatus main body. ing. Also, the toner described later is often stored in the toner cartridge and designed to be removable from the main body of the image forming apparatus. When the toner in the used toner cartridge runs out, this toner cartridge is removed. It can be removed from the main body of the image forming apparatus and another new toner cartridge can be mounted. Further, a cartridge equipped with all of the electrophotographic photosensitive member 1, the charging device 2, and the toner may be used.

  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, LEDs, and the like. Further, exposure may be performed by a photoreceptor internal exposure method. 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 type of the developing device 4 is not particularly limited, and an arbitrary device such as a dry development method such as cascade development, one-component conductive toner development, two-component magnetic brush development, or a wet development method 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 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 restricting 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 toner T is arbitrary, and in addition to the powdery toner, a polymerized toner using a suspension polymerization method, an emulsion polymerization method, or the like can be used. In particular, when a polymerized toner is used, a toner having a small particle diameter of about 4 to 8 μm is preferable, and the toner particles are used in various shapes ranging from a nearly spherical shape to a shape outside the spherical shape on the potato. be able to. The polymerized toner is excellent in charging uniformity and transferability and is suitably used for high image quality.

  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 that are disposed 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.

  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.

  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. Each of the upper and lower fixing members 71 and 72 includes a fixing roll in which a metal base tube such as stainless steel or aluminum is coated with silicon rubber, a fixing roll in which Teflon (registered trademark) resin is coated, and a fixing sheet. A member can be used. 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.
The type of the fixing device is not particularly limited, and a fixing device of any type such as heat roller fixing, flash fixing, oven fixing, pressure fixing, etc. can be provided including those used here.

  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. This 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.

  EXAMPLES Hereinafter, although an Example demonstrates this invention further in detail, this invention is not restrict | limited to a following example, unless it deviates from the summary.

<Synthesis Example 1>
A reaction vessel was charged with 150 g of hydrogenated polybutadiene polyol (1) having an repeating structure represented by the following formula (I) (1) (trade name: Polytail H, manufactured by Mitsubishi Chemical Corporation) and 300 ml of toluene. It melted by heating at 70 ° C. To this was added dropwise 9.7 g of phosphorus tribromide over 20 minutes, 150 ml of water was added to what was heated and stirred at 70 ° C. for 1 hour, neutralized with an aqueous sodium carbonate solution, and released into 2 L of methanol. . The precipitate was filtered off and washed with methanol to obtain 151 g of hydrogenated polybutadiene bromide.

  140 g of the bromide, 25 g of parahydroxyphenyl-diphenylamine, 9.6 g of tetrabutylammonium bromide, and 375 ml of tetrahydrofuran were charged, and 8.2 g of potassium hydroxide was added over 30 minutes while heating and refluxing tetrahydrofuran. After heating and refluxing with stirring for 5 hours, the reaction solution was discharged into a water-methanol (1/4) mixture, and the resulting precipitate was collected by filtration, and further washed with a water-methanol (1/4) mixture. By hang-washing, 146 g of a crude product containing a compound having a structure represented by the following formula (II) was obtained.

<Example 1>
(Manufacture of materials)
The crude product containing the compound of the above formula (II) was dissolved in 900 ml of toluene, 35 g of activated clay was added, and the mixture was heated and stirred at 70 ° C. for 30 minutes. After the activated clay was filtered off, 35 g of activated clay was added again, followed by filtration at 70 ° C. for 30 minutes, and the treated toluene solution was released into methanol. The produced precipitate was collected by filtration to obtain 143 g of a white solid. This is referred to as an electrophotographic photosensitive material of Example 1.

(Create photoconductor)
10 parts of oxotitanium phthalocyanine showing a clear peak at a diffraction angle 2θ ± 0.2 ° of 27.3 ° in a powder X-ray diffraction pattern by CuKα ray, polyvinyl butyral (manufactured by Denki Kagaku Kogyo Co., Ltd., trade name: # 6000C) 5 parts of 1,2 dimethoxyethane was added and pulverized and dispersed in a sand grind mill. The dispersion thus obtained was applied on a polyethylene terephthalate film having aluminum deposited on the surface so as to have a film thickness of 0.3 μm to provide a charge generation layer.

  Next, on this film, 50 parts of a hole transporting compound having a structure represented by the following formula (III), 100 parts of a binder resin having a structure represented by the following formula (IV), and the electrophotographic photoreceptor of Example 1 A solution prepared by dissolving 5 parts of the material and 0.03 part of silicone oil as a leveling agent in a mixed solvent of toluene and tetrahydrofuran was applied, air-dried, dried at 125 ° C. for 20 minutes, and the film thickness after drying was 20 μm. A charge transport layer was provided so that This is referred to as an electrophotographic photosensitive member of Example 1.

(Measurement of electrical characteristics)
The electrophotographic photosensitive member of Example 1 was mounted on a photosensitive member characteristic evaluation apparatus installed in an environmental test room at a temperature of 25 ° C. and a relative humidity of 50%. After charging the surface potential of the photoreceptor to −700 V, irradiation with 780 nm light was performed while changing the irradiation intensity, and the surface potential after 100 milliseconds was measured. Table 9 shows the residual potential (Vr, unit V) and half-exposure amount (E / 2, unit μJ / cm ² ) at that time.

<Comparative Example 1>
The electrophotographic photoreceptor was prepared in the same procedure as in Example 1 except that the crude product containing the compound of formula (II) obtained in Synthesis Example 1 was used as it was as a material for an electrophotographic photoreceptor without purification. It was prepared (this is the electrophotographic photosensitive member of Comparative Example 1), and the electrical characteristics were measured. The results are shown in Table 9.

<Synthesis Example 2>
200 g of a mixture of branched primary alcohols having 32, 34, and 36 carbon atoms (trade name NJECOAL C32-36, manufactured by Shin Nippon Rika Co., Ltd.) and 400 ml of toluene were charged into a reactor equipped with a thermometer and a reflux condenser. 55 g of phosphorous tribromide was added dropwise while stirring at a temperature of ° C. After reacting for 1 hour, an aqueous sodium carbonate solution was added for neutralization, and the entire amount was released into 3 l of methanol, and the resulting precipitate was collected by filtration to obtain 98 g of a branched alkyl bromide having 32 to 36 carbon atoms.

  Next, 20.5 g of tetramethylbisphenol F represented by the following structural formula (hereinafter referred to as “TmBPF” as appropriate), 15.5 g of tetrabutylammonium bromide, 13.5 g of potassium hydroxide, and 250 ml of tetrahydrofuran were added to a thermometer. The reactor was charged with a reflux condenser and heated to 60 ° C. with stirring. To this, 98 g of branched alkyl bromide having 32 to 36 carbon atoms was added and reacted under reflux for 6 hours. To this reaction solution, 300 ml of toluene was added and washed with water three times. The organic phase was reprecipitated with 3 l of methanol to obtain 101 g of a pale yellow crude TmBPF branched alkyl 2-adduct.

<Example 2>
(Manufacture of materials)
After passing a solution obtained by dissolving a crude TmBPF branched alkyl diadduct in a mixed solvent of toluene and hexane through a column filled with silica gel, the solvent is once distilled off, and further dissolved in 200 ml of toluene, and activated clay 12. After adding 5 g and stirring at 60 ° C. for 30 minutes, the activated clay was removed by filtration. Further, similarly, treatment with activated clay (12.5 g) once, activated carbon (2.5 g) once and activated clay (12.5 g) twice is performed, and the solvent is distilled off to purify a colorless viscous liquid. 39 g of product was obtained. This is referred to as an electrophotographic photoreceptor material of Example 2.

(Create photoconductor)
On the same aluminum vapor-deposited polyethylene terephthalate film as in Example 1, a charge generation layer was provided according to the same procedure as in Example 1. Subsequently, on this film, 60 parts of the hole transporting compound of the above formula (III), 100 parts of the binder resin having the structure shown in the following formula (V), 10 parts of the compound prepared in Example 2, and silicone as the leveling agent A solution prepared by dissolving 0.03 part of oil in a mixed solvent of toluene and tetrahydrofuran was applied, air-dried, and then dried at 125 ° C. for 20 minutes, and a charge transport layer was provided so that the film thickness after drying was 20 μm. . This is the electrophotographic photoreceptor of Example 2.

  The electrophotographic photoreceptor of Example 2 was measured for electrical characteristics according to the same procedure as in Example 1. The results are shown in Table 10.

<Comparative example 2>
An electrophotographic photosensitive member was prepared in the same procedure as in Example 2 except that the crude TmBPF branched alkyl 2-adduct obtained in Synthesis Example 2 was used as it was as a material for an electrophotographic photosensitive member without purification (this is the same). And the electrophotographic photosensitive member of Comparative Example 2), and the electrical characteristics were measured. The results are shown in Table 10.

  As is clear from the results of Tables 9 and 10, the electrophotographic photoreceptors of Examples 1 and 2 that were used after the crude product containing a compound having a specific structure was purified with an adsorbent, the composition was used as it was. Compared with the electrophotographic photoreceptors of Comparative Examples 1 and 2 used as the above, the residual potential is small and the sensitivity is high.

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

Explanation of symbols

1 Photoconductor 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 (paper, medium)

Claims (6)

In an electrophotographic photosensitive member formed by forming a photosensitive layer having a layer containing at least a binder resin on a conductive support, it is contained in the layer in a range of 30 parts by weight or less with respect to 100 parts by weight of the binder resin. A method for producing a material for an electrophotographic photoreceptor,
A material for an electrophotographic photosensitive member, characterized by contacting a compound represented by the following general formula (1) and / or a crude product containing a compound represented by the following general formula (2) with an adsorbent: Production method.
(In the general formula (1), A represents a linear or branched, saturated or unsaturated aliphatic hydrocarbon group having 20 to 500 carbon atoms. X represents a divalent linking group. B represents an aromatic hydrocarbon group which may have a substituent having a formula weight of 500 or less, or a hydrogen atom, and n represents an integer of 1 to 5.)
(In general formula (2), C represents an optionally substituted hydrocarbon group having a formula weight of 2000 or less and having two or more aromatic rings. Y represents a divalent linking group. D Represents a linear or branched, saturated or unsaturated aliphatic hydrocarbon group having 10 to 500 carbon atoms, and m represents an integer of 1 to 10.) 2. The method for producing a material for an electrophotographic photosensitive member according to claim 1, wherein C in the general formula (2) has a structure represented by the following formula (3).
(In formula (3), R ¹ Represents a hydrogen atom, a halogen atom, a substituted or unsubstituted aliphatic hydrocarbon group, a substituted or unsubstituted aromatic hydrocarbon group, Z represents a linking group, q represents an integer of 1 to 10, p Represents an integer of 0 to 4. ) The method for producing a material for an electrophotographic photosensitive member according to claim 1 , wherein the crude product is brought into contact with the adsorbent in a state where the crude product is dissolved in an organic solvent having a boiling point of 40 ° C. or higher. An electrophotographic photoconductor material produced by the method for producing an electrophotographic photoconductor material according to any one of claims 1 to 3 . An electrophotographic photosensitive member formed by laminating a photosensitive layer having a layer containing at least a binder resin on an electroconductive support, according to claim 4 wherein the binder resin 100 parts by weight of an electrophotographic photoreceptor material described in the layer An electrophotographic photosensitive member, which is contained in an amount of 30 parts by weight or less based on the above .   100 weight of the binder resin obtained by contacting a binder resin and a crude product containing a compound represented by the following general formula (1) and / or a compound represented by the following general formula (2) with an adsorbent A method for producing an electrophotographic photosensitive member, comprising forming a photosensitive layer having a layer containing 30 parts by weight or less of the material for an electrophotographic photosensitive member with respect to parts on a conductive support.
(In the general formula (1), A represents a linear or branched, saturated or unsaturated aliphatic hydrocarbon group having 20 to 500 carbon atoms. X represents a divalent linking group. B represents an aromatic hydrocarbon group which may have a substituent having a formula weight of 500 or less, or a hydrogen atom, and n represents an integer of 1 to 5.)
(In general formula (2), C represents an optionally substituted hydrocarbon group having a formula weight of 2000 or less and having two or more aromatic rings. Y represents a divalent linking group. D Represents a linear or branched, saturated or unsaturated aliphatic hydrocarbon group having 10 to 500 carbon atoms, and m represents an integer of 1 to 10.)