JPH02294654A - Electrophotographic photoreceptor having a light-receiving layer containing a polysilane compound - Google Patents

Abstract

PURPOSE:To improve sensitivity and durability by incorporating a specific polysilane compd. into the photoreceptive layer of the electrophotographic sensitive body having the photoreceptive layer on a conductive base. CONSTITUTION:The electrophotographic sensitive body has the photoreceptive layer formed by using the polysilane compd. which is expressed by formula I and has 6000 to 200000 weight average mol. wt. In the formula I, R1 denotes 1 or 2C alkyl group, R2 denotes 3 to 8C alkyl group, etc.; R3 denotes 1 to 4C alkyl group; R4 denotes 1 to 4 alkyl group; A, A' are respectively 4 to 12C alkyl group, etc.; n and m are the molar ratio indicating the respective nonomer numbers to the total monomer in the polymer where n+m=1 and 0<n<=1, 0<=m<1. The sensitivity, the durability and the stability to an environmental change are improved in this way.

Description

DETAILED DESCRIPTION OF THE INVENTION [Technical field to which the invention pertains] The present invention relates to an electrophotographic photoreceptor using an organic material. More particularly, the present invention relates to electrophotographic photoreceptors having photoreceptive layers formed using novel polysilane compounds that provide improved electrophotographic properties. [Description of the Prior Art] Various organic photoconductive polymers, including polyvinyl carbazole, have been proposed as organic photoconductive materials for use in electrophotographic photoreceptors. Although these polymers are superior in terms of film formability and light weight compared to inorganic photoconductive materials, it has been difficult to put them into practical use until now because they still have sufficient film formability. This is because they are inferior to inorganic photoconductive materials in terms of permeability, durability, and stability against environmental changes. Also, as an organic photoconductive material for electrophotographic photoreceptors, U.S. Patent No. 4,1
Hydrazone compounds are disclosed in US Pat. No. 50,987, and triarylvirazoline compounds are described in US Pat.
9-styrylanthracene compounds were proposed in JP-A No. 828 and JP-A No. 5194829, respectively.
They are of low molecular weight. However, none of these low-molecular-weight organic photoconductive materials can solve the film-forming problems that have been a problem in the field of organic photoconductive polymers by appropriately selecting the binder used. Although there are some, the sensitivity is not sufficient and it is not of practical use in obtaining a desired electrophotographic photoreceptor. For this reason, in recent years, the photosensitive layer has been changed to 1! A laminated structure with functionally separated charge generation layer and charge transport layer has been proposed.
Electrophotographic photoreceptors having this lfIta layer as a photosensitive layer can now be improved in terms of sensitivity to visible light, charge retention, surface strength, etc. Such an electrophotographic photoreceptor is disclosed in, for example, US Pat. No. 3,837,85
It is disclosed in Specification No. 1, Specification No. 3,87 1,88 2, etc. However, when conventional low-molecular organic photoconductive materials are used to create the charge transport, the organic photoconductive materials are mixed with a predetermined binder resin. For this reason, the resulting electrophotographic photoreceptor has low charge mobility due to the binder resin, and does not necessarily have sufficient sensitivity and characteristics. Polysilanes are subject to large fluctuations and lack sufficient durability. Therefore, polysilanes are attracting attention as photoconductive materials that have the potential to produce desired organic electrophotographic photoreceptors. By the way, there are reports that so-called polysilane is insoluble in solvents;
Journal of AmericanC
chemical Society) soil 25,2291pp
(1924)], it has recently been reported that polysilanes are soluble in solvents and can be formed into films. [The Journal of American Ceramic Society]
American Ceramic Society)
6 1, 504pp (1978)]. Furthermore, it has been reported that polysilane has the property of a photosemiconductor in which charge can be transferred through the σ-bond of the dome [Physical Review (Piysical Review)].
Review), B 35, 2818pp (19
8 7)). For these reasons, it is hoped that polysilane will be used in electrophotographic photoreceptors. However, in order to obtain a desired electrophotographic photoreceptor that is of practical use by using polysilane as a photoconductive material, it is necessary to use polysilane as follows. It is required that at least the following requirements are met. That is, these requirements are (i) not only to be soluble in solvent and capable of forming a film, but also to be able to form a film without minute defects and with high homogeneity; (ii)
Since minute defects are not tolerated in photoreceptors for photosensitive photography, the substituents must also have a clear structure and be of high quality so as not to cause abnormalities in film formation. Although several reports have been made regarding the synthesis of polysilane, none of the reported polysilanes is sufficient for use in electrophotographic photoreceptors. That is, low molecular weight polysilanes having a structure in which all Si groups are substituted with organic groups have been reported or proposed [The Journal of the American Chemical Society].
ican Chemical Society), Vo
l. 9 4, Ha 1 1, 3806pp(1
9 7 2 冫], Tokuko Sho 63-38033). The product described in the former publication has a structure in which the end group of dimethylsilane is replaced with a methyl group, and the product described in the latter publication has a structure in which the end group of dimethylsilane is replaced with an alkoxy group. However, the degree of polymerization is 2 to 6 in all cases,
Does not exhibit macromolecular characteristics. In other words, due to its low molecular weight, it does not have film-forming ability as it is, making it difficult to use industrially. A high molecular weight polysilane with a structure in which all St groups are substituted with organic groups has recently been reported [Nikkei Pneumateria No. 8/15 issue, page 46 (1988)], L
However, because it involves a special reaction intermediate, a decrease in the synthesis yield is expected, making industrial mass production difficult. In addition to the above report, a method for synthesizing polysilane has been reported [The Journal of Organometallic Chemistry].
(ometallic chemistry), 1
9 8 ppC27 (1980), or The Journal of Polymer Science, Polymer Chemistry
f PolymerScience, Pa! ymer
Chet*istry E+Htion), Vo
l. 22 159-I70pp (see 1984)
．． However, all of the reported synthesis methods involve only the condensation reaction of the polysilane main chain, and there is no mention of terminal groups. In any synthesis method, unreacted chloro groups and byproducts are produced due to side reactions, making it difficult to consistently obtain the desired polysilane compound. There are some examples of using the above-mentioned polysilane as a photoconductor (U.S. Pat. No. 4,618,551;
772525, JP-A No. 62-269964), it is thought that this is due to the influence of unreacted chlorine groups and by-products due to side reactions. That is, according to U.S. Pat. No. 4,618,551, the polysilane compound described above is applied to an electrophotographic photoreceptor, and image formation using the electrophotographic photoreceptor is performed using a general copying machine based on the absolute value of the surface potential. Although the value may be between 500 and 800■, the surface potential has an abnormally large absolute value, i.e. -t
This is done in ooov. This eliminates the problem of defects in the electrophotographic photoreceptor due to structural defects in polysilane at a potential with a normal absolute value, resulting in spot-like abnormal phenomena in the resulting image. This is thought to be to ensure that Furthermore, according to Japanese Patent Application Laid-Open No. 62-269964, an electrophotographic photoreceptor was prepared using the above-mentioned polysilane compound and its photosensitivity was measured, but the photosensitivity was slow and It is understood that this material has no advantages over known selenium photoreceptors and mesophotoreceptors. As mentioned above, conventional polysilanes still have many problems when used in electronic materials, and cannot be used industrially. (Object of the Invention) The main object of the present invention is to provide an electrophotographic photoreceptor that satisfies various requirements for an electrophotographic photoreceptor and has a photoreceptive layer made of an organic photoconductive material. Another object of the present invention is to provide an electrophotographic photoreceptor having a photoreceptor layer formed using a specific polysilane compound with a novel use and particularly excellent in sensitivity and durability. Still another object of the present invention is to provide an electrophotographic photoreceptor having a light-receiving layer formed using a novel specific polysilane compound that has good solubility in a solvent and excellent film-forming ability. [Configuration and Effects of the Invention] The present invention achieves the above-mentioned objects, and the electrophotographic photoreceptor provided by the present invention has the following general formula (+
), and the weight average molecular weight is 6,000 to 20,000.
It is characterized by having a photoreceptive layer formed using a polysilane compound of 0. R + R s person - ESi publication - "-ichimo Sto→ko"18'...C
0R g R a [However, in the formula, R is an alkyl group having 1 or 2 carbon atoms/R
! is an alkyl group having 3 to 8 carbon atoms, a cycloalkyl group,
Ryoryl group or aralkyl group, R3 represents an alkyl group having 1 to 4 carbon atoms, R4 represents an alkyl group having 1 to 4 carbon atoms, A and A' each represent an alkyl group having 4 to 12 carbon atoms, cyclo It is an alkyl group, an aryl group, or an aralkyl group, and both may be the same or different. n and m are the molar ratios indicating the proportion of each heptanomer number to the total monomers in the polymer, n+m=l
So, O<n≦1, 0≦m<1. ] The following describes how the polysilane compound represented by the general formula (1) used in the present invention is objectively distinguishable from known polysilane compounds. That is, conventionally known polysilane compounds are obtained by, as described above, using a dichlorosilane monomer as a starting material, removing halogen from the monomer using an Na catalyst, and polymerizing it. Most of them have a halogen residue at the end. When such conventional polysilane compounds containing halogen residues are used as constituent materials for the light-receptor of electrophotographic photoreceptors, the resulting electrophotographic photoreceptor has the following problems. Therefore, it is of no practical value. That is, in an electrophotographic photoreceptor having a photoreceptive layer composed of the conventional polysilane compound, when an image is formed using the photoreceptor, the halogen residue acts as a trap for charge transfer, reducing the residual potential. This results in Further, when repeatedly charging and exposing to light, the residual potential increases and the bright area potential increases accordingly, resulting in poor durability. In addition to these problems, there are also other problems. That is, when the halogen residue of the conventional polysilane compound containing halogen residues constituting the photoreceptor is CIl5, when moisture is present, the CI group reacts with the moisture to form hydrogen chloride gas (HC1). This causes corrosion of the conductive portion of the electrophotographic photoreceptor substrate that is in contact with the photoreceptive layer, resulting in poor conductivity and resulting in image defects. On the other hand, the polysilane compound used in the present invention is represented by the above monocatalytic formula (1) and has a weight average molecular weight of 6,000 to 20
0,0 0 0 and does not have a halogen group, does not involve side reactions like the conventional polysilane compounds mentioned above, is easily soluble in organic solvents, and completely dissolves without turbidity. It is characterized by differentiating matters, such as being able to realize the following properties, having excellent film forming ability, and making the resulting film transparent without local defects. The present inventors have developed a polysilane compound having no halogen residue and having a weight average molecular weight of 6,000 to 200,000, which is represented by the above-mentioned general formula (1) and is suitable for electrophotographic photoreceptors. We investigated through experiments whether it is suitable as a constituent material for the photoreceptive layer. The results revealed the following. That is, the following was found out about the polysilane compound itself. (i) It is stable with no side reactions in the usage environment; (ii) it is easily soluble in existing solvents and can be completely dissolved without turbidity; and (iii)
) It has an excellent film forming ability: (iv) The resulting film is transparent without any local defects; and (v) It has an excellent charge transport ability, and extremely fast charge mobility is observed. .

When the polysilane compound was applied to the photoreceptive layer of an electrophotographic photoreceptor, the following was found. In other words, it becomes an electrophotographic photoreceptor that has high sensitivity and produces high-quality images without defects: (b) There is no generation of troughs or bulges, and the residual potential during exposure is extremely small: {C} Excellent charge When the polysilane compound is used in combination with a charge generating substance, it is possible to provide an electrophotographic photoreceptor with excellent electrophotographic properties. As described above, the present invention is based on the general formula (1
), and the weight average molecular weight is 6,000 to 2
A polysilane compound having no halogen residue of 0 0,0 0 0 is suitable as a constituent material of a photoreceptive layer of an electrophotographic photoreceptor, and the photoreceptor layer is formed using a polysilane compound. It was discovered and completed that the photoreceptor for electrophotography has the various advantages mentioned above. used in the present invention,
It is represented by the above general formula (1) and has a weight average molecular weight of 6,0
The polysilane compound having a molecular weight of 0 to 20,000 is
It has no chlorine group or side reaction-generating group, and all St groups are substituted with a specific m group that does not have oxygen,
Non-toxic, aromatic solvents such as toluene, benzene, xylene, etc., dichloromethane, dichloroethane, chloroform, carbon tetrachloride, etc., and other solvents such as tetrahydrofuran (THF), dioxane, etc. It is easily soluble in solvents and has excellent film-forming ability. The film formed using the polysilane compound is homogeneous, has a uniform thickness, has excellent heat resistance, is rich in hardness, and is rich in toughness. As mentioned above, the polysilane compound represented by the general formula (+) used in the present invention has a weight average molecular weight of 6,000 to 200,000, but its solubility in a solvent is From the viewpoint of film-forming ability, those with a weight average molecular weight of s, o o
o to 120,000, and the optimal one has a weight average molecular weight of 10,000 to 80,00.
0 0. Regarding the weight average molecular weight,
Those with a value of 6,000 or less do not exhibit the characteristics of polymers and have no film-forming ability. Also, 200,00
If it is 0 or more, it has poor solubility in solvents, making it difficult to form the desired film. Further, in the above-mentioned polysilane compound represented by the above-mentioned general formula (+) used in the present invention, when particularly strong toughness is desired for the film to be formed, the terminal @ groups A and A' are
The group is preferably selected from the group consisting of an alkyl group having 5 to 12 carbon atoms, a cycloalkyl group having 5 to 12 carbon atoms, an aryl group, and an aralkyl group. In this case, the most preferred polysilane compound used in the present invention is one in which the terminal groups A and A' are groups selected from an alkyl group having 5 to 12 carbon atoms and a cycloalkyl group having 5 to 12 carbon atoms. It is. The above polysilane compound used in the present invention can be synthesized as follows. That is, under a high-purity inert atmosphere free of oxygen and moisture, a dichlorosilane monomer is brought into contact with a condensation catalyst made of an alkali metal to perform halogen elimination and condensation polymerization to synthesize an intermediate polymer. The intermediate polymer is separated from unreacted monomers, and the intermediate polymer is reacted with a specified halogenated organic reagent in the presence of a condensation catalyst made of an alkali metal to condense the existing organic groups at the ends of the polymer. It will be done. In the above synthesis operation, the dichlorosilane monomer as the starting material, the intermediate polymer, the halogenated organic reagent, and the alkali metal condensation catalyst are all highly reactive with oxygen and moisture. Under the existing atmosphere, the desired polysilane compound mentioned above cannot be obtained. Therefore, the above-mentioned operation for obtaining the above-mentioned polysilane compound used in the present invention needs to be carried out in an atmosphere in which neither oxygen nor moisture is present. Therefore, care must be taken regarding the reaction container and all reagents used to avoid the presence of either oxygen or moisture in the reaction system. For example, for the reaction vessel, perform vacuum suction and argon gas replacement in a blow box to prevent moisture and oxygen from adsorbing into the system. In any case, the argon gas used is dehydrated by passing it through a silica gel force column in advance, and then passing the copper powder through a column heated to 100°C to deoxidize it before use. The dichlorosilane monomer, which is the starting material, is introduced into the reaction system after being distilled under reduced pressure using the above-mentioned argon gas, which has been deoxygenated immediately before introduction into the reaction system.
The halogenated organic reagent and the solvent used for introducing a specific organic group are also deoxidized in the same manner as the dichlorosilane monomer before being introduced into the reaction system.
Note that the solvent is deoxidized by distilling it under reduced pressure using the deoxygenated argon gas described above, and then further dehydrating it with metallic sodium. The above condensation catalyst is used in the form of wires or chips, and the wires or chips are formed in an oxygen-free paraffinic solvent to prevent oxidation. The dichlorosilane monomer as a starting material used in producing the polysilane compound represented by the above general formula (+) used in the present invention has the general formula:
A silane compound represented by R IR t S i C It t or this and the general formula: R, R. A silane compound represented by SiCI is selectively used. The above-mentioned condensation catalyst is preferably an alkali metal capable of causing a condensation reaction by eliminating halogen, and specific examples of the alkali metal include lithium, sodium, and potassium, with lithium and sodium being preferred. The above-mentioned halogenated backbone reagent is for introducing substituents represented by A and A', and is used to introduce substituents represented by A and A', from halogenated alkyl compounds, halogenated cycloalkyl compounds, halogenated aryl compounds, and halogenated aralkyl compounds. A suitable compound selected from the group consisting of formula 1a:
A-X and/or general formula iA'-X (however, Xl; tC
1 or Br), and appropriate compounds from the specific examples described below are selectively used. General formula used when synthesizing the above intermediate polymer: R+RtSiClx or this and general formula: R s
The dichlorosilane monomer represented by R a S I C 1 z is dissolved in a predetermined solvent and introduced into the reaction system, and a paraffinic non-polar hydrocarbon solvent is preferably used as the solvent. ．． Preferred examples of the solvent include n-hexane, n-octane, n-nonane, n-
Examples include dodecane, cyclohexane and cyclooctane. Since the intermediate polymer produced is insoluble in these solvents, it is convenient to separate the intermediate polymer from unreacted dichlorosilane monomer. The separated intermediate polymer is then reacted with the halogenated organic reagent mentioned above, in which case both are dissolved in the same solvent and subjected to the reaction. In this case, aromatic solvents such as benzene, toluene, and xylene are preferably used as the solvent. When condensing the above-mentioned dichlorosilane monomer using the above-mentioned alkali metal catalyst to obtain a desired intermediate, the degree of polymerization of the resulting intermediate polymer can be controlled as appropriate by adjusting the reaction temperature and reaction time. ．． However, it is desirable to set the reaction temperature at this time between 60°C and 130°C. A desirable embodiment of the method for producing the above-mentioned polysilane compound represented by the above-mentioned general formula (1) used in the present invention described above will be described below. That is, the method for producing the above-mentioned polysilane compound used in the present invention consists of (i) a step of producing an intermediate polymer, and (ii) a step of introducing substituents A and A' at the terminals of the intermediate polymer. ．． The step (i) above is performed as follows. That is, the reaction system in the reaction vessel is completely free of oxygen and moisture and is controlled by argon to maintain a predetermined internal pressure, an oxygen-free paraffin solvent and an oxygen-free condensation catalyst are added, and then an oxygen-free dichloromethane is added. Add silane monomer,
The monomers are condensed by heating the whole to a predetermined temperature while stirring. At this time, the degree of condensation of the dichlorosilane monomer is controlled by adjusting the reaction temperature and reaction time so that an intermediate polymer having a desired degree of polymerization is produced. In this reaction, as shown in reaction formula (i) below, the chloro group of the dichlorosilane monomer and the catalyst cause a desalting reaction, and the Si groups repeat condensation to form a polymer, producing an intermediate polymer. do. Catalyst nR+Rz SrCI,+mR3Ra sic7! ，
→RI Rs C I -ES iEto 『117 Sif C J...
・ (i) t Rz R4 The specific reaction procedure at this point is to prepare a catalyst (alkali metal) in a paraffinic solvent,
Add the dichlorosilane monomer dropwise while stirring under heating. The degree of polymerization is determined by sampling the reaction solution. Polymerization can be easily confirmed by pumping the sample liquid and checking whether a film can be formed. As the condensation progresses and a polymer is formed, it becomes a white solid that precipitates out of the reaction system. After cooling, the solvent containing the heptamer is separated from the reaction system by decantation to obtain an intermediate polymer. Next, the step (bl) described above is carried out. That is, the chlorine group at the end group of the obtained intermediate polymer is subjected to desalting condensation using a halogenated active agent and a condensation catalyst (alkali metal) to convert the end group of the polymer to a predetermined state. Substitution with an organic group. The reaction at this time is represented by the following reaction formula (ii). R+ R3 I C1 -←S toner 1--1-÷Sl-}-T- Cj
lR, Rt A -ES i issue 1r-110S i-+1-A'
・=(ii)R! R a Specifically, an aromatic solvent is added to an intermediate polymer obtained by condensation of a dichlorosilane monomer to dissolve it. Next, a condensation catalyst (alkali metal) is added, and a halogenated W agent is added dropwise at room temperature. At this time, in order to compete with the condensation reaction between the polymer end groups, the halogenated organic agent is added at a rate of 0.00% relative to the starting monomer. Ol~O. Add 1x excess of it. Gradually heat and stir at 80°C to 100°C for 1 hour to carry out the desired reaction. After the reaction is complete, cool and add methanol to remove the alkali metal of the catalyst. Next, the polysilane compound produced is extracted with toluene and purified using a silica gel ram. The desired polysilane compound used in the present invention is thus obtained.

+ (2A-X or A-X+A'-X)
Eleven? RS: Clt and RJa SiCl Note: Among the following compounds, a-2 to 16, 18.2
0.21, 23.24 are used for R+Rz SICI g, a-1+2. lI. l7, 19, 22.23.
25 is RJ4 SiCl! Used for. (013) zsic 1 1 a-1 ((Oli)tclDtsicj!! a-22 ((Oh)ic)zsicj!t A-X and A'-X's (013) tcIIcll,C 1 Oh(Oft)4cj! CI13 (011) sir a et al. (a'Z) lJr b-14 b-15 As the catalyst, an alkali metal is preferred.

Lithium, sodium, and potassium are used as alkali metals. It is preferable to use a wire-like or chip-like shape to increase the surface area. C2115 cH3 Ql3 (Clh) s-4: Si +T-(OIJ
sol*c-18 01(Oh)t Qls Q'l3 Ctl (Cth) z CIlffi 01z 01i Note) 2. Both X and Y in the above structural formula represent polymerized units of halogen. Then, n can be found from the calculation formulas: The electrophotographic photoreceptor of the present invention basically comprises: an electrically conductive support, and the above-mentioned polysilane compound provided on the support (i.e., the above-mentioned C-1 to C-1). and a photoreceptive layer containing a polysilane compound selected from C-43. (In addition, the "photoreceptive layer" in the present invention
generally refers to a layer provided on a conductive support.
) The photoreceptive layer may be composed of a single layer or may be composed of a plurality of functionally separated layers. A typical example of the electrophotographic photoreceptor of the present invention in which the photoreceptive layer is a single layer is shown schematically in FIG. In FIG. 1, 101 is a conductive support, and 102 is a photoreceptive layer containing the above-mentioned polysilane compound. In this case, the photoreceptive layer 102 is made of the above-mentioned polysilane compound [i.e.
This is a so-called photosensitive layer containing a substance that causes charge transport (charge transport substance 'l>) and a substance that causes charge generation (hereinafter referred to as "charge generation substance").First
The electrophotographic photoreceptor of the type shown in the figure has an undercoat layer (see the figure) which has a barrier function and an adhesive function between the conductive support and the photosensitive layer (photoreceptive layer 102), if necessary. (not shown), and may also have a surface protective layer on the photosensitive layer (photoreceptive layer 102) to protect the calendar. It may have a layer (not shown). In the case of the electrophotographic photoreceptor of the form shown in FIG. The ratio (charge generating substance: charge transporting substance) is preferably 1.
:100 to 1:1, more preferably 1:20 to 1
; Both substances are contained in a ratio of 3:3, and the layer thickness is preferably 4 to 30 μm, more preferably 7 to 20 μm. As the above-mentioned charge generating substance, there are 8! A charge generating substance or a known inorganic charge generating substance can be selectively used. Examples of these organic charge-generating substances include azo # pigments, phthalocyanine pigments, anthoanthro pigments, quinone pigments, biratron #1 pigments, indigo IIfft4, quinacridone pigments, and biryllium dyes. Also, no a
Examples of @-carrying substances include selenium, selenium-tellurium, and selenium-arsenic. The photosensitive layer (ie, photoreceptive layer I02) of the electrophotographic photoreceptor of the type shown in FIG. 1 can be formed, for example, as follows. That is, first, a suspension is prepared by dispersing a predetermined amount of the above-mentioned electrostatic generating substance in a suitable melt, and a predetermined amount of the polysilane compound (the above-mentioned C-t to C-t) is added to the resulting suspension. A coating liquid is prepared by dissolving a polysilane compound selected from C-43. The obtained t-liquid is coated on the surface of a conductive support by an appropriate coating means in an amount such that the layer thickness after drying falls within the above-mentioned predetermined thickness range, and the formed liquid coat is coated by a known means. Dry and solidify. The solvent used at this time includes benzene,
Aromatic solvents such as toluene and xylene; halogen solvents such as dichloromethane, dichloroethane, and chloroform;
In addition to these, tetrahydrofuran, dioxane, etc. can be mentioned. Examples of the coating method include a wire bar method, a dipping method, a doctor plate method, a spray method, a roll method, a bead method, and a spin coating method. When the above-mentioned subbing layer is provided on the electrophotographic photoreceptor shown in FIG. 1, its NyL is preferably 4 to 30.
It is desirable that the thickness be 7 to 20 μm, more preferably 7 to 20 μm. S sublayer is casein, polyvinyl alcohol, diF
Cellulose, bolyamide (nylon 6, nylon 6G)
, nylon 610, copolymerized nylon, alkoxymethylated nylon, etc.), polyurethane, and aluminum oxide.
To form the undercoat layer, if the material for the undercoat layer to be used is soluble in a solvent, prepare a coating liquid by dissolving it in an appropriate solvent, or if the material is insoluble in the solvent. In the case of a photosensitive layer, a coating liquid is prepared by dispersing the resin in a binder resin solution, and the resulting coating liquid is applied to the surface of the conductive support 101 in the same manner as in the case of forming the photosensitive layer described above. This is done by coating to form a liquid coat, which is then dried and solidified. Further, when the above-mentioned surface protective layer is provided on an electrophotographic photoreceptor of the type shown in FIG.
The range is 1 to 5 μm. The surface protective layer is composed of a resin such as polycarbonate A, polycarbonate Z, polyarylate, polyester, or polymethyl acrylate. Note that the surface protective layer may contain additives such as resistance adjusting agents and deterioration inhibitors. The surface protective layer is formed by dissolving the resin in a suitable solvent to prepare a coating liquid, and using the obtained coating liquid in the same manner as in the case of forming the photosensitive layer described above. This is done by coating the surface of a photosensitive layer to form a liquid coat, which is then dried and solidified. When the above-mentioned resistance modifier or anti-deterioration agent is contained in the surface protective layer, the formed surface protective layer contains such additives by uniformly dispersing such additives in the coating liquid for the above-mentioned surface protective layer. This is where it is contained. When the electrophotographic photoreceptor of the present invention has a photoreceptive layer composed of a plurality of functionally separated layers, it typically has the form shown in FIG. 2 or FIG. 3. That is,
The electrophotographic photoreceptor of the present invention having the form shown in FIG. 2 is provided on a conductive support 201! A charge generating layer 202 containing a charge generating substance and a charge generating layer 203 containing the above-mentioned polysilane compound are laminated in this order from the support 201 side, and as shown in FIG. The electrophotographic photoreceptor of the present invention has a charge transport layer 302 containing the above-mentioned polysilane compound and a charge generation layer 303 containing a charge generation substance on a g-conducting support 301. It is made by stacking layers in this order from the side.

The electrophotographic photoreceptor of the present invention in the form shown in FIGS. 2 and 3 is similar to the electrophotographic photoreceptor in the form shown in FIG. (not shown) and/or surface protection (not shown). That is, the undercoat layer is provided between the conductive support 201 and the trt1 generation layer 202 in the case of the electrophotographic photoreceptor of the form shown in FIG. In the case of a photoconductor, a conductive support 301 and a charge transport layer 30
2. Regarding the surface protective layer,
In the case of the electrophotographic photoreceptor shown in FIG. 2, it is provided on the charge transport layer 203, and in the case of the electrophotographic photoreceptor shown in FIG. Second
? of the form shown in Figures and Figure 3? ! In an electrophotographic photoreceptor having a charge generation layer (202 or 303) and a charge transport layer (203 or 302), the layer thickness of both layers is determined so that the electrophotographic photoreceptor exhibits desired electrophotographic properties. is one of the important requirements. That is, in the case of the electrophotographic photoreceptor shown in FIG. 2, the charge generation layer 202 preferably has a thickness of 0. The layer thickness of the charge transport layer 203 is from 4 to 30 μm, more preferably from 7 to 20 μm.
It is desirable to set it to llW.

In the case of the electrophotographic photoreceptor of the form shown in FIG. 3, the charge transport layer 302 is preferably 4 to 30 μm thick, more preferably 7 to 20 μm thick. and the charge generation N303 is preferably 1 to 15 μm, more preferably 3 to 1 μm.
It is desirable to have a layer thickness of 0 μm. Further, when a subbing layer is provided on the electrophotographic photoreceptor shown in FIG. 2 or 3, the layer I7 preferably has 4 to 3
0 μm, more preferably 7 to 20 μm. Similarly, when a surface protective layer is provided, the layer thickness is preferably 0.
It is 1 to 5 μm. Charge generation layer 202 or 303
As the charge-generating substance contained in the charge-generating substance, a known charge-generating substance or a known inorganic charge-generating substance can be used. Such an organic? Specific examples of Ii-generating substances include azo pigments, phthasilocyanine pigments, anthoanthrone pigments, quinone pigments, pyranthrone pigments, indigo pigments, quinacridone pigments, and biryllium pigments. Similarly, specific examples of inorganic charge-generating substances include selenium, selenium-tellurium, selenium-arsenic, and the like. ! The charge-generating layer 202 or 303 can be formed by depositing the above-mentioned charge-generating substance by a known method or by the method described above! It can be formed by preparing a coating liquid containing a charge-generating substance, applying the coating liquid, and drying and solidifying the coating liquid. Of these two methods, the latter method is more preferable. That is, according to the latter method, charge generators are formed! @Distribution in the desired state into the generation layer can be easily achieved. The specific content of the latter method is to prepare a coating liquid in which the charge generating substance is uniformly dispersed by using a suitable dispersion medium and introducing the charge generating substance into a suitable solvent together with the dispersion medium. Apply liquid coat 1
. The charge generation layer 202 or 303 is formed by drying and solidifying the liquid coat. Desirable examples of the decomposition medium include so-called binder resins such as insulating resins and organic photoconductive polymers. Specific examples of such binder resins include polyvinyl butyral, polyvinyl benzal, polyarylate, polycarbonate, polyester, phenoxy resin,
Examples include cellulose resin, acrylic resin, polyurethane, etc. In addition to these, if necessary,
The above-mentioned polysilane compounds used in the present invention can also be used as the dispersion medium. In either case, the amount of the dispersion medium used is determined by the content (weight ratio) in the finally formed charge generation layer (202 or 203).
The content is preferably 80% by weight or less, more preferably 40% by weight or less.

Further, as the solvent, a solvent that dissolves the above-mentioned binder resin and allows the above-mentioned charge generating material to be uniformly dispersed in the dissolved binder resin is selectively used. Specific examples of such solvents include, for example, ethers such as tetrahydrofuran and 1,4-dioxane; ketones such as nclohexanone and methyl ethyl ketone; Amides such as N-dimethylformamide; Esters such as methyl acetate and ethyl acetate; Aromatics such as toluene, xylene, and chlorobenzene; Alcohols such as methanol, ethanol, and 2-brobanol; Chloroform, methylene chloride, and dichloroethylene. , carbon tetrachloride, aliphatic halogenated hydrocarbons such as trichloroethylene, etc. Any known appropriate coating method can be used to form a liquid coat by applying the above-mentioned coating liquid. Such coating methods include wire bar coating method, dipping method, Dr.Frede method, spray method, roll method, bead method, spin coating method, etc. In addition, the formed charge generation layer (20
A dry solidification method that does not cause any damage to 2 or 303) can be adopted. The charge transport layer 203 or 302 containing the polysilane compound described above can be formed by the same method as in the case of forming the charge generation layer (202 or 303) described above. That is, the charge transport layer preferably contains a polysilane compound selected from the above-mentioned c-i to C-43 in a proportion of 5 to 30% of the solvent.
It can be formed by dissolving it in a solvent in an amount of % by weight, more preferably IO to 20% by weight, applying this to form a liquid coat, and drying and solidifying the liquid coat. Examples of the solvent include aromatic solvents such as benzene, toluene, and xylene, halogen solvents such as dichloromethane, dichloroethane, and chloroform, and in addition to these solvents, tetrahydrofuran, dioxane, and the like.
Application of the coating liquid and drying and solidification of the liquid coat can be performed in the same manner as in the formation of the charge generation layer (202 or 303). The electrophotographic photoreceptor of the form shown in FIG.
When an undercoat layer and/or a surface protective layer are provided in the electrophotographic photoreceptor of the form shown in the figure, both of these layers are similar to those described for the electrophotographic photoreceptor shown in FIG. It can be formed using a method. The electroconductive support (10 i.201.30
Let me explain 1). First of all, regarding the shape, cylindrical,
It can be of any shape, such as a belt or a plate. Next, regarding the constituent materials, the entire structure may be electrically conductive, or the base may be an insulating material and the surface on which the light-receiving layer is provided may be electrically conductive. Specific examples of the former include metal members such as aluminum, copper, and zinc, and alloys such as aluminum alloys and stainless steel. In the latter case, the above-described metal coating is formed on the surface of a plastic base member made of polyethylene, polypropylene, polyvinyl chloride, polyethylene terephthalate, acrylic resin, etc. by a known vacuum deposition method, or the plastic base member A member whose surface is coated with conductive particles such as titanium oxide, tin oxide, carbon black, and silver using an appropriate binder resin, and an impregnated base member such as paper or plastic is impregnated with the conductive particles. You can list the parts that have been removed. In addition to these members, a member obtained by coating the surface of a suitable metal heath member with the above-mentioned conductive particles using a suitable binder resin can also be used as the above-mentioned conductive support. In addition, in any of the electrophotographic photoreceptors shown in FIGS. 1 to 3 described above, when forming the next constituent layer on the previously formed horizontal layer, the solvent used may be different from the one formed earlier. It is important to select and use a solvent that does not dissolve the constituent layers. The electrophotographic photoreceptor of the present invention described above is applicable not only to various electrophotographic copying machines, but also to laser beam printers, CRT printers, LED printers, liquid crystal printers, laser engravings, and the like.

[Production Examples of Polysilane Compounds Used in the Present Invention] Below, specific production methods for the polysilane compounds used in the present invention will be explained with reference to production examples, and the usefulness of the polysilane compounds will also be explained. In addition, in the production examples and comparative production examples described below, the presence or absence of Cl groups is first confirmed for the product, and if the presence of CI groups is confirmed, its quantification is performed, and its abundance is determined in the product. It is expressed as the number of millimeters per 1000 grams. Further, the obtained product was checked by FTiR and/or UV spectrum to determine whether it was a polysilane compound having a main chain consisting of a long horizontal Si--Si bond. Furthermore, in conjunction with this, the presence or absence of bonding of substituents in the side chains was confirmed by examining by FT-IR and/or by examining protons in the substituents by FTNMR. Based on the results obtained above, the structure of the synthesized product was determined. The above-mentioned confirmation of the presence or absence of CI groups in the product is performed using fluorescence xi
Analyzer (fully automatic fluorescence X'ilA analyzer system 30
80 F (manufactured by Rigaku Denki Kogyo Co., Ltd.).
At that time, trimethylchlorosilane (manufactured by Chisso Co., Ltd.) was prepared as a standard sample, and 1.5.10.50,
Keyaki TL solutions were prepared by diluting each of them 100 times, and each standard solution was applied to the fluorescent X-ray analyzer to measure the amount of CI group, and a calibration curve was determined based on the obtained results.
On the other hand, for the product to be tested, a test sample was prepared by dissolving 1 gram of the product in dehydrated toluene to a total volume of 10μ, which was measured using the fluorescent X-ray analyzer, and the measurement results were obtained. The amount of Cl groups was determined by comparing it with the above inspection line. For measurement by FT-IH, a KBr pellet of the test sample is prepared, and this is coated with NicoeL FT-1 1775.
0 (manufactured by Nikolay Japan). Also, FT-NMI? For measurement, the test sample is dissolved in CDCi and subjected to FT-NMR.
The measurement was carried out by setting it on FX-90 (manufactured by JEOL Ltd.). In addition, in the Uv spectrum, if the polysilane compound is a low-molecular one, the spectrum will be closer to the short wavelength side, and if it is a polymer, the spectrum will be closer to the long wavelength side. Bride Chemistry (Pure & App
Lied Chemistry) 5↓, ms. pp.
1041-1050 (1982). 1
1l1L Prepare a three-necked flask in a Blowbo 7x that has been vacuum suctioned and replaced with argon, attach a Refranox condenser, temperature needle, and dropping funnel to it, and supply argon gas from the bypass pipe of the dropping funnel. I passed it. 100 g of dehydrated dodecane and 0.3 mol of wire-shaped sodium metal were placed in this three-necked flask and heated to 100° C. with stirring. Next, dichlorosilane monomer
(manufactured by Chisso ■) (a-7) 0.1 mol of dehydrated dodecane 3
The prepared solution was slowly added dropwise to the reaction system. After the dropwise addition, a white solid was precipitated by condensation polymerization at 100°C for 1 hour. After that, it is cooled, the dodecane is decanted, and then 10% of dehydrated toluene is added.
The white solid was dissolved by adding 0 grams and 0.01 mole of sodium metal was added. Next, a solution prepared by dissolving 0.01 mol of n-hexyl chloride (manufactured by Tokyo Kasei) (b3) in toluene 1 O + w1 was slowly added to the reaction system while stirring, and the mixture was heated at 100°C. It was heated for 1 hour. After cooling, 50 m7 of methanol was slowly added dropwise to remove excess metal sodium. This produced a suspended layer and a toluene layer. Next, the toluene layer was separated, concentrated under reduced pressure, and purified by development using a silica gel column and chromatography to obtain a product with a yield of 65%. For this product, 01
When measured using the group content measurement method, no CI groups were found (i.e., 0 in 1000 grams of sample).
．． 00 mmol equivalent》. In addition, the weight average molecular weight of this product was determined by GPC method.
When measured by HF development, it was found to be 75,000 (using boristyrene as a standard).The product was subjected to FT-IRaW determination using the above-mentioned method, and then FT-NMR measurement. , Si-Cl bond, Si-
It was found that there were no 0-St bonds or S I -0-R bonds, and the product was found to be a polysilane compound having the structure of C-1 described above. The above results are shown in Table 4. ufii A Nitro flask was prepared in a Brovo Nox that had been vacuum-suctioned and replaced with argon, and a reflux condenser, temperature needle, and dropping funnel were attached to it, and argon gas was passed through the bypass pipe of the dropping funnel. In this three-necked flask, 100 grams of dehydrated dodecane and 1
0.3 mol of 1 square of metallic lithium was charged and heated to 100°C with stirring. Next, a solution prepared by dissolving 0.1 mole of dichlorosilane monomer (Ha-7 manufactured by Chisso ■) in 30 grams of dehydrated dodecane was slowly added dropwise to the reaction system. After the dropwise addition, a white solid was precipitated by condensation polymerization at 100°C for 2 hours. After cooling, the dodecane was decanted and 100 grams of dehydrated toluene was added to dissolve the white solid, and 0.02 mole of metallic lithium was added. Next, chlorhenzene (manufactured by Tokyo Kasei) (b-5) 0
．． A solution prepared by dissolving 0.02 mol in 10 liters of toluene was slowly added dropwise to the reaction system with stirring, and heated at 100° C. for 1 hour. After this, in order to cool down and process excess metallic lithium, use 50 liters of methanol! was slowly dripped. This produced a suspended layer and a toluene layer. Next, after dividing the toluene layer and excavating it under reduced pressure, it was developed using a silica gel column and chromatography to produce T#.
Polysilane compound 112 (tji formula: C-3) was obtained. The yield was 72%, and the weight average molecular weight was 92.0
It was 0 0. The results are shown in Table 4. Breaking Procedure 1 - Prepare a three-necked flask in a blow box that has been vacuum-suctioned and replaced with argon, attach a reflux condenser, thermometer, and dropping funnel to it, and supply argon gas from the bypass pipe of the dropping funnel. passed through. 100 grams of dehydrated n-hexane and 0.3 mol of 1 square meter of metallic sodium were charged into this three-necked flask, and heated to 80° C. with stirring. Next, 0.1 mol of dichlorosilane monomer (manufactured by Chisso ■) (a-7) was dehydrated n-
A solution prepared by dissolving it in hexane was slowly added dropwise to the reaction system. After the dropwise addition, a white solid was precipitated by condensation polymerization at 80°C for 3 hours. After this, the white solid was melted by cooling, performing n-hexane'lctecantation, and adding 100 grams of dehydrated toluene.
0.01 mol of metallic sodium was added. Next, a solution prepared by dissolving 0.0 l of penzyl chloride (manufactured by Tokyo Kasei) (b-12) in lO-1 of tonolene was slowly added dropwise to the reaction system with stirring, and the mixture was heated to 80°C. It was heated for 1 hour. After cooling, 50 liters of methanol was slowly added dropwise to remove excess metal sodium. This produced a suspended layer and a toluene layer. Next, the toluene layer was separated, concentrated under reduced pressure, and purified by development using a silica gel column and chromatography to obtain a polysilane compound Nn3 (structural formula: C4). Yield is 6
1%, and the weight average molecular weight was 47,000. The results are shown in Table 4. In addition, in this polysilane compound, unreacted Si-CI and by-product Si-
There was no IR absorption attributed to 0-Si or SiO-R. Polysilane compound No. 4 (Structure 2: C-6) and polysilane compound were synthesized in the same manner as in Example 3 using the dichlorosilane monomer and end group treatment agent shown in Table 1. Disease 5
(Structural formula: C-2) in yields of 60% and 62%, respectively. t. In addition, in this polysilane compound, unreacted Si-CI, by-product Si-0-S
There was no IR absorption assigned to i, S t -0-R. The identification results are summarized in Table 4. Comparison 1] ■ Condensate dichlorosilane monomer (manufactured by Chinoso ■) (a-7) in the same manner as in Example 3, and synthesize f A polysilane compound +kXD-1 having the structural formula shown in Table 4 was obtained.
The yield was 60%, and the weight average molecular weight was 46,000. The results are shown in Table 4. In addition, in this polysilane compound, unreacted Si-Cj! is present in the terminal group. , an IR absorption attributed to the by-product Si-0-R was observed. Polymerization was carried out in the same manner as in Example 3, using dichlorosilane monomers shown in Table 2 and varying the reaction times as shown in Table 2. In addition, the compounds shown in Table 2 were used as end group treatment agents. The synthesized product was purified in the same manner as in Production Example 3, thus producing polysilane compounds 6-I shown in Table 4.
O-t-obtained. The yield and weight average molecular weight of each polysilane compound obtained were as shown in Table 4. In addition, in any polysilane compound, unreacted S i-C
j! , by-product Si-0-Si. Si-0-R {+
Polysilanes shown in Table 4 were synthesized in exactly the same manner as in Production Example 6, except that the reaction time of the dichlorosilane monomer in Main Production Example 6 was changed to 10 minutes. Compound D-2 was obtained.

The yield and weight average molecular weight of the polysilane compound obtained were as shown in Table 4. In addition, the obtained polysilane compound contains unreacted Si-CI and by-product S.
i-0-S i. There was no R absorption assigned to Si-0-R. Production Examples 11 to 14 Synthesis was carried out in the same manner as in Example 1 using the dichlorosilane monomers and end group treatment agents shown in Table 3 to obtain polysilane compounds Nhl1 to ml4 shown in Table 4. The yield and weight average molecular weight of each polysilane compound obtained were as shown in Table 4. Prepare a three-necked flask in a blowfuchs that has undergone main vacuum suction and argon replacement, and attach a reflux condenser, thermometer, and dropping funnel to it, and gas the argon gas from the bypass pipe of the dropping funnel. passed through. Dehydrated dodecane 1. 00 grams and 0.3 mol of wire metal sodium were added and heated to 100°C with stirring. Next, a solution prepared by dissolving 0.1 mole of dichlorosilane monomer (manufactured by Chisso Ql) in 30 grams of dehydrated L'decane was slowly dropped into the reaction system. After the dropwise addition, a white solid was precipitated by condensation polymerization at 100°C for 1 hour. After that, 50ml of methanol was used to cool and remove excess metal sodium.
j! was slowly dripped. Next, the white solid was collected by filtration and washed repeatedly with n-hexane and methanol.
I got 3. This polysilane compound contains toluene, chloroform, TH
It was insoluble in organic solvents such as F. The results were as shown in Table 4.

．． fL comparison next twist ↓ Place a three-necked flask in a blowbonox that has been vacuum suctioned and replaced with argon, attach a reflux condenser, thermometer, and dripping CI-}, and supply argon from the bypass pipe of the dropping funnel. Passed the gas. 100 grams of dehydrated dodecane and 0.3 mole of wire-shaped sodium metal were placed in this three-necked flask and heated to 100° C. with stirring. Next, a solution prepared by dissolving 0.1 mole of diphenyl dichlorosilane monomer (manufactured by Chinoso 11) in 30 grams of dehydrated dodecane was slowly dropped into the reaction system. After the dropwise addition, a white solid was precipitated by condensation polymerization at 100° C. for 1 hour.

After this, it is cooled and the excess metal sodium is disposed of.
50 ml of methanol was slowly added dropwise, and then the white solid was collected by filtration and washed again with n-hexane and methanol to obtain polysilane compound D-4 shown in Table 4.

This vorisolane compound was insoluble in organic solvents such as toluene, chloroform, and THF. The results are shown in Table 4. Table 1 [Example] The electrophotographic photoreceptor having a photoreceptive layer containing the polysilane compound of the present invention will be further explained below with reference to Examples. It is not limited in any way. An electrophotographic photoreceptor of the type shown in Part 2 of the above article was prepared. 5 with the size of IOCIIXIOCI1 as the support 201
An aluminum substrate with a thickness of 0 μm was used. First, a charge is generated II2 on the surface of the aluminum substrate as follows.
02 was formed. That is, a coating liquid for charge generation 11202 was prepared by dispersing 10 parts by weight of chloraluminum phthalocyanine and 5 parts by weight of polyvinylbunaral in 90 parts of methyl ethyl ketone, and the resulting coating liquid was dispersed in a ball mill. The film thickness after drying is 0 on the surface of the aluminum substrate.
．． A charge generating layer 202 with a thickness of 0.3 μm is formed by coating with a wire bar in an amount of 3 μm to form a liquid coat and drying.
was formed. Next, 20% by weight of the polysilane compound obtained in Production Example (ml of polysilane compound shown in Table 4) was dissolved in 80% by weight toluene to form charge transport layer 2.
A coating liquid for 03 was prepared.The obtained coating liquid was applied to the surface of the previously formed charge generation layer 202 using a wire bar in an amount such that the film thickness after drying would be IO μm to form a liquid coat.
It was dried to form a transport layer 203 with a thickness of IO μm, and a photoreceptor for electrophotography (V: Thl) was applied. The obtained electrophotographic photoreceptor samples were evaluated from various viewpoints. That is, the electrophotographic photoreceptor sample was corona charged at -5 KV using an electrostatic copying paper tester ModθI SP-428 manufactured by Kawaguchi Denki ■, and then charged at -5 KV in a dark place.
After holding the sample for 2 seconds, it was exposed to light at an illuminance of 2.5 lux to examine its photosensitivity, and then further exposed to strong light (illuminance: 20 lux/second) to eliminate static electricity. Regarding the charging characteristics, the potential after ti seconds of the corona band (V,)
The exposure amount (El/2) required to attenuate the voltage to 172 was measured. Also, the residual potential VXt after strong exposure was measured, and the initial residual potential was V'! I set it to L. Furthermore, the electronic magawa spectrophotometer sample was transferred to Canon K.K. K. Made by P
Paste it on the photoreceptor tram cylinder of the PC copy fiNP-1502 and attach it to the photosensitive tram cylinder. I set it on a Ji photocopier, made copies, and evaluated the initial images. Next, 500 copies were made in succession, and the images after 500 copies were evaluated. Next, the electrophotographic photoreceptor sample on the photoreceptor drum cylinder after copying the 500 sheets is taken out from the copying machine, removed from the photoreceptor drum cylinder, and the sample is removed from the photoreceptor drum cylinder. Test equipment Model SP
-428, check the charging characteristics, and residual potential (Vs
The variation amount (ΔV sL) of L) was measured. The evaluation results obtained are as shown in Table 5. Each polysilane compound obtained in Production Example 2.3.4 and 5 (polysilane compound IF!2.3 shown in Table 4)
．． Four types of electrophotographic photoreceptors of the type shown in FIG. ). Each photoreceptor sample obtained was evaluated in the same manner as in Example 1. The evaluation results obtained are as shown in Table 5. Figure 2 shows the same procedure as in Example I except that the polysilane compound obtained in Comparative Production Example 1 (polysilane compound NID-1 shown in Table 4) was used as the material for forming the charge transport layer. A type of electrophotographic photoreceptor was manufactured (sample floor E-1).
．． The obtained photoreceptor samples were evaluated in the same manner as in Example 1, and the evaluation results are shown in Table 5.

Examples of manufacturing Susashikan Tamajitoe 6, 7, 8. Example 1 was carried out in the same manner as in Example 1, except that the polysilane compounds obtained in Examples 9 and IO (polysilane compounds N16, 7.8.9 and 10 shown in Table 4) were used as the material for forming the charge transport layer. An electrophotographic photoreceptor of the type shown in FIG. 2 was manufactured with a 4F@neck (trial t1 Arashi 6 to 10).

Each photoreceptor sample obtained was evaluated in the same manner as in Example 1. The evaluation results obtained are as shown in Table 5.

Comparison coin-1 Photoreceptor for electrophotography of the type shown in Figure 2 (sample pigeon E-2
) The process up to the formation of the charge generation layer 202 was carried out in the same manner as in Example 1. Next, the polysilane compound obtained in Comparative Production Example 2 (polysilane compound 1bD-2 shown in Table 4) was dissolved in toluene to prepare a coating liquid for forming the charge transport layer 203, and this coating liquid was first formed. charge generation N
When a liquid coat was formed by coating the surface of No. 202 in an amount to give a film thickness of 10 μm after drying and drying, cracks appeared and an angry photoreceptor could not be obtained. Four types of electrophotographic photoreceptors of the type shown in Figure 2 were prepared (Samples Arashi 11 to 14). As the support 201, an aluminum b.
A coating liquid was prepared by dispersing 10 parts by weight of the diazo pigment represented by +) and 5 parts by weight of polybutylbutyral in 90 parts by weight of methyl ethyl ketone, and the coating liquid was applied to the surface of the aluminum substrate so that the film thickness was 0 after drying. A liquid coat was formed by applying an amount of 0.2 μm using a wire coater, and was dried to form a charge generating layer 1202 having a thickness of 0.2 μm. Regarding the charge transport layer 203, the polysilane compound used was changed for each sample. That is, each of the polysilane compounds obtained in Production Examples 1l to 14 (polysilane compounds lhll to l4 shown in Table 4) was used. The charge transport layer 203 of each sample was formed using these polysilane compounds in the same manner as in Example 1. Each of the photoreceptor test grains subjected to #4 was evaluated using the same evaluation method as in Example 1. The evaluation results obtained are as shown in Table 5. Each of the polysilane compounds obtained in Comparative Production Examples 3 and 4 (polysilane compounds of lhD-3 and &D-4 shown in Table 4) was subjected to N.I. r@ Two types of electrophotographic photoreceptors (sample Koji E-3 and sample E-14) were prepared in the same manner as in Example 1 except that material r1 was used for forming the transport layer. However, both mD-3 and lhD-4 polysilane compounds were insoluble in the specified 8iUA medium, and the desired photoreceptor could not be obtained. ``Husband Aiming'' j22 LL Insert 5 photoreceptors for electrophotography in the evening and eve shown in Figure 2!゛目Y袈L7tac jA: t. : iKi 15 to 19).
As the support 201, 5 with a size of 10csX10cm
An aluminum substrate with a thickness of 0 μm was used. Charge generation layer 2
For the formation of No. 02, a coating liquid was prepared by dispersing 10 parts by weight of a diazo pigment represented by the following structural formula (II) and 1 part of polycarbonate 51i in 90 parts by weight of tetrahydrofuran using a ball mill. A liquid coat was formed on the surface of an aluminum substrate using a wire bar to form a film thickness of 0.3 μm after drying, and then dried to form a charge generation layer 202 with a thickness of 0.3 μm. Regarding charge transport H203, the polysilane compound used was changed for each sample. That is, each of the polysilane compounds obtained in Production Examples 1 to 5 (polysilane compounds Ilkll to 5 shown in Table 4) was used. The charge transport layer 203 of each sample was formed using these polysilane compounds in the same manner as in Example 1. Each photoreceptor sample obtained was evaluated using the same evaluation method as in Example 1. The evaluation results obtained were as shown in No. 5 Jl. Electrophotographic photoreceptor of the type shown in Figure 3 (sample positive 20)
An aluminum substrate with a size of 10 cm×I ocs and a thickness of 5 μm was used as the support 301. First, a charge transport layer 302 was formed on the surface of the aluminum substrate. That is, the polysilane compound obtained in Production Example 1 (polysilane compound positive 1 shown in Table 4) was 20! ffffi part 8
A coating liquid for forming the electrical transport layer 302 is prepared by dissolving it in 0 parts of toluene, and the obtained coating liquid is applied to the surface of the aluminum substrate using a wire bar with a 1tA thickness of 10 μm after dry explosion. to form a liquid coat and dry it for 10 days.
A charge transport layer 302 with a thickness of 1 um was formed. Then the following ('
) tlla 5 parts by weight of dipromanthanthrone (manufactured by Hoechst) represented by formula (III) and 11.0 parts by weight of the above-mentioned polysilane compound Nl were dispersed in 85 parts by weight of toluene by a ball mill to form a charge generation layer 303. A coating liquid was prepared and the resulting coating liquid was applied to the previously formed coating liquid. cargo fta
A liquid coat is formed on the surface of the feeding layer 302 by using a wire bar in an amount that will give a film thickness of 3 μm after drying, and is dried to form a liquid coat.
A charge generation layer 303 with a thickness of μm was formed to obtain an electrophotographic photoreceptor (sample 20). The obtained electrophotographic photoreceptor sample was evaluated using the evaluation method in Example 1. The evaluation results obtained are as shown in Table 5. Example 3 was prepared in the same manner as in Example 20, except that the material for forming charge transport 111302 was the polysilane compound obtained in Comparative Production Example 1 (polysilane compound NID-1 shown in Table 4).
Electrophotographic photoreceptor of the type shown in the figure (sample ll & 1.
E-5) was produced. The obtained electrophotographic photoreceptor sample was evaluated using the same evaluation method as in Example 1.
The evaluation results obtained are as shown in Table 5. In Example 20, polysilane compound-1 was replaced with the polysilane compound NID described above in forming the charge generation layer 303.
An electrophotographic photoreceptor (trial 14mE-6) was produced in the same manner as in Example 20, except that -1 was used instead. The obtained electrophotographic photoreceptor sample was evaluated using the same evaluation method as in Example 1. The evaluation results obtained are as shown in Table 5. Electrophotographic photoreceptor of the type shown in Fig.
2 1) was created. As the support 101, lOcmX
An aluminum substrate with a size of 5 μm and a thickness of 5 μm was used. Photosensitive J! 1102 It was formed like Haggi.
That is, 51i parts of berylene represented by the following structural formula (1'/) (trade name Ninovopermlade BL, manufactured by Hoechst) and the polysilane compound obtained in Production Example 14 (the polysilane compound shown in Table 4) -14) 1 part of 20t to 7 parts of toluene
A coating liquid was prepared by dispersing it in a ball mill in 5 parts by weight. The obtained coating liquid was applied to the surface of the aluminum substrate using a wire bar in an amount such that the thickness after drying would be 12 μm, to form a liquid coat, and the liquid coat was dried to form a photosensitive layer 102 having a thickness of 12 μm. In this way, an electrophotographic photoreceptor (Sample-21) was obtained. The obtained electrophotographic photoreceptor sample was evaluated using the same evaluation method as in Example 1.

The evaluation results obtained are as shown in Table 5. ,b Mosquito Killing J1 In Example 2l, an electrophotographic photoreceptor (trial i4NQB-7
) was obtained. The obtained electrophotographic photoreceptor sample was evaluated using the same evaluation method as in Example 1. The evaluation results obtained were as shown in Table 5.

[Brief explanation of drawings]

FIG. 1 is a schematic cross-sectional view of an electrophotographic photoreceptor having a single-layer photoreceptor layer according to the present invention. FIGS. 2 and 3 are schematic cross-sectional views of an electrophotographic photoreceptor in which the light-receiving layer provided by the present invention is composed of a plurality of layers, respectively. In the figure, 101.201.301... conductive support, 102.
...Photosensitive layer, 202.303...Charge generation layer, 203.302...Charge transport layer.

Claims (2)

[Claims] (1) An electrophotographic photoreceptor having a photoreceptive layer on a conductive support, wherein the photoreceptor layer contains a polysilane compound represented by the general formula (I) and having a weight average molecular weight of 6,000 to 200,000. A photoreceptor for electrophotography characterized by the following. ▲There are mathematical formulas, chemical formulas, tables, etc.▼...(I) [However, in the formula, R_1 is an alkyl group with 1 or 2 carbon atoms,
R_2 represents an alkyl group having 3 to 8 carbon atoms, a cycloalkyl group, an aryl group, or an aralkyl group, R_1 represents an alkyl group having 1 to 4 carbon atoms, and R_4 represents an alkyl group having 1 to 4 carbon atoms. A and A' are each an alkyl group, a cycloalkyl group, an aryl group, or an aralkyl group having 4 to 12 carbon atoms, and they may be the same or different, and n and m are the total amount in the polymer. It is a molar ratio indicating the ratio of the number of each monomer to the monomer, and n
+m=1, 0<n≦1, 0≦m<1. ] (2) In general formula (I), A and A' have 5 carbon atoms
An electrophotographic photoreceptor comprising the polysilane compound according to claim 1, which is represented by 1 to 12 alkyl groups or cycloalkyl groups.