JP3043792B2 - Polysilane copolymer and method for producing the same - Google Patents

Description

Description: TECHNICAL FIELD The present invention relates to a polysilane copolymer and a method for producing the same.

[Description of Prior Art]

Polysilane was reported to be insoluble in solvents [The Journal of American Chemical Society, Vol. 125, p. 2291 (1924)]. It was reported that [Journal of the American Ceramic Society, Vol. 61, pp. 504 (1978)], and has gained attention. Furthermore, studies have been made on the application of polysilanes to resists because they cause photodecomposition by ultraviolet irradiation (JP-A-60-98431 and JP-A-60-119550).

In addition, polysilane has the property of an optical semiconductor capable of transferring charges by σ-bonds in the main chain [Physical Review B, Vol. 35, p. 2818 (1987)], and is expected to be applied to electrophotographic photoreceptors. It became so. However, for application to such electronic materials, it is necessary that the polysilane compound not only has a solvent solubility and a film forming ability, but also can form a film without fine defects and can form a film with high homogeneity. . Since a fine defect is not allowed in an electronic material, a high-quality polysilane compound which has a clear substituent structure and does not cause an abnormality in film formation is required.

Polysilane is a brittle film in terms of mechanical properties because it is easy to take one-dimensional structure [Solid State Physics, Vol. 22, No. 11, p. 907 (1987)]. Since polysilane is hard and brittle, it undergoes heat shrinkage during film formation to generate cracks, is weak against bending, and has poor contact properties, and tends to cause peeling. Furthermore, if there is a contact object on the surface, it is easy to scrape and the wear resistance is poor.

There have been various reports on synthesis studies of polysilane compounds, but there are still problems in using them for electronic materials. Low-molecular-weight polysilane compounds having a structure in which all Si groups are substituted with organic groups have been reported [The Journal of American Chemical Society (Jo
urnal of American Chemical Society), Vol. 94, No. 11
No. 3806 (1972)] and JP-B-63-38033]. The former publication has a structure in which a terminal group of dimethylsilane is substituted with a methyl group, and the latter publication has a structure in which a terminal group of dimethylsilane is substituted with an alkoxy group. Also have a degree of polymerization of 2 to 6 and do not exhibit the characteristics of a polymer. In other words, because of its low molecular weight, there is no film forming ability as it is, and it is difficult to use it industrially. A high-molecular-weight polysilane compound having a structure in which all Si groups are substituted with organic groups has recently been reported [Preprints of the Society of Inorganic Polymer Research Society, 2 pages (February 9, 1989)]. However, since the reaction proceeds via a special reaction intermediate, a decrease in the synthesis yield is expected, and industrial mass production is difficult.

Also, the synthesis method of the polysilane compound is described in The Journal of Organometallic Chemistry, page 198, C27.
(1980) or The Journal of Poimer Science, Polymer Chemistry Edition, 22nd edition
Volume, pp. 159-170 (1984). However, in any of the reported synthesis methods, only the condensation reaction of the polysilane main chain is performed, and there is no mention of a terminal group.
In any of the synthesis methods, unreacted chloro groups and by-products are produced by side reactions, and it is difficult to constantly obtain a desired polysilane compound.

Examples of using the above-mentioned polysilane compounds as photoconductors have also been reported (U.S. Pat. No. 4,618,551, U.S. Pat. No. 4,772,525, JP-A-62-269964).
JP-A No. 2000-209, and the effects of unreacted chloro groups and by-products due to side reactions are presumed.

In the above-mentioned U.S. Pat.No. 4,618,551, the polysilane compound is used as an electrophotographic photoreceptor, but in a general copying machine, the applied potential may be 500 to 800 V, but an abnormally high applied potential of 1000 V is used. I have. It is considered that this is because an abnormal potential causes a defect in the electrophotographic photosensitive member due to a structural defect of polysilane, thereby eliminating a spot-like abnormal phenomenon on an image. In Japanese Patent Application Laid-Open No. 62-269964, an electrophotographic photoreceptor is prepared using the above-mentioned polysilane compound, and the photosensitivity is measured. Has no advantage over photoreceptors.

Further, in U.S. Pat.No. 4,772,525, the polysilane compound is used as an electrophotographic photosensitive member,
It has been reported that cracks easily occur in solvents.

Although the content of this description increases the molecular weight of polysilane to improve solvent resistance, it does not improve the mechanical properties inherent in polysilane, and it is not hard, brittle, poor in adhesion, and abrasion resistance. Has not been improved.

As described above, in order to use polysilane as an electronic material, many problems still remain, and a polysilane compound that can be used industrially has not yet been provided.

[Object of the invention]

An object of the present invention is to provide a polysilane copolymer composed of a silane monomer unit and an organic monomer unit, and a method for producing the same.

Another object of the present invention is to have excellent mechanical properties, toughness,
An object of the present invention is to provide a polysilane copolymer having good adhesion and excellent abrasion resistance and a method for producing the same.

Another object of the present invention is to provide a polysilane copolymer having good solvent solubility and excellent film-forming ability, and a method for producing the same.

Still another object of the present invention is to provide a polysilane copolymer useful for producing various electronic devices and medical instruments, and a method for producing the same.

[Structure and effect of the invention]

The present invention achieves the above object and provides a polysilane copolymer represented by the following general formula [I] and a method for producing the same.

(Wherein, R ₁ is an alkyl group having 1 or 2 carbon atoms, R ₂ is an alkyl group having 3 to 8 carbon atoms, cycloalkyl group, aryl group or aralkyl group, and R ₃ is an alkyl group having 1 to 4 carbon atoms. R ₄ represents an alkyl group having 1 to ₄ carbon atoms, R ₅ represents a hydrogen atom or a methyl group, and A and A ′ each represent an alkyl group having 4 to 12 carbon atoms, a cycloalkyl group, an aryl group or an aralkyl group. Or substituted silyl groups, which may be the same or different, wherein n, m and p are
It is a molar ratio indicating the ratio of the number of each monomer to the total monomer in the polymer, and n + m + p = 1, and 0
<N <1, 0 ≦ m <1, 0 <p <1. Q represents 0 or 1. The polysilane copolymer of the present invention is a copolymer obtained by condensing a silane monomer and an organic monomer, and has no toxicity.
Aromatic solvents such as toluene, benzene, xylene, halogenated solvents such as dichloromethane, dichloroethane, chloroform, carbon tetrachloride, and other tetrahydrofuran (TH
It is easily soluble in solvents such as F) and dioxane, and has excellent film-forming ability. In the present invention, the film formed from the polysilane copolymer has a uniform and uniform thickness, has excellent heat resistance, is rich in hardness and is rich in toughness.

For these reasons, the polysilane copolymer provided by the present invention can be used for manufacturing electronic devices, medical devices, and the like, and is a high-molecular-weight substance having high industrial utility.

The electronic device includes an organic photoconductor, an electric conductor, a photoresist, an optical information storage element, and the like. Examples of the medical device include artificial organs, artificial blood vessels, and blood transfusion bags.

The above-mentioned polysilane copolymer provided by the present invention can be synthesized as follows. That is, under a high-purity inert atmosphere without oxygen and moisture, a dichlorosilane monomer and a dichloroorganic monomer are brought into contact with a condensation catalyst comprising an alkali metal or magnesium to perform halogen elimination and polycondensation to synthesize an intermediate polymer. Separating the obtained polymer from unreacted monomers, and reacting the polymer with a predetermined halogenated organic reagent and a halogenated silane in the presence of a condensation catalyst composed of an alkali metal or magnesium to form an organic compound at the terminal of the polymer. It is synthesized by condensing a group and a silyl group.

In the above synthesis operation, the starting materials dichlorosilane, dichloroorganic monomer, the intermediate polymer, the halogenated organic reagent, the halogenated silane and the alkali metal or magnesium condensation catalyst are all reactive with oxygen or moisture. Because of the high polysilane copolymer content, the above-mentioned polysilane copolymer intended for the present invention cannot be obtained in an atmosphere in which oxygen or moisture exists.

Therefore, the above-described operation for obtaining the polysilane copolymer of the present invention needs to be performed in an atmosphere in which neither oxygen nor moisture exists. For this reason, it is necessary to pay attention to all of the reaction vessels and the reagents used so that neither oxygen nor moisture is present in the reaction system. For example, for a reaction container, vacuum suction and argon gas replacement are performed in a blow box so that moisture and oxygen are not adsorbed in the system. The argon gas used is
In any case, the powder is dehydrated by passing through a silica gel column in advance, and then the copper powder is passed through a column heated to 100 ° C. to be deoxygenated before use.

The dichlorosilane monomer and the dichloroorganic monomer, which are the starting materials, are introduced into the reaction system after performing vacuum distillation using the above-described degassed argon gas immediately before introduction into the reaction system. The halogenated organic reagent for introducing a specific organic group, the halogenated silane, and the solvent to be used are also introduced into the reaction system after being subjected to deoxygenation treatment similarly to the dichlorosilane monomer. In addition,
In the deoxidizing treatment of the solvent, the solvent is distilled under reduced pressure using the above-described deoxidized argon gas, and then further dehydrated with metallic sodium.

The above-mentioned condensation catalyst is used in the form of a wire or chip. The wire or chip is used in an oxygen-free paraffin-based solvent to prevent oxidation.

The starting material dichlorosilane monomer used in producing the polysilane copolymer represented by the general formula (I) of the present invention is a silane compound represented by the following general formula: R ₁ R ₂ SiCl ₂ or And a silane compound represented by the general formula: R ₃ R ₄ SiCl ₂ is selectively used.

The dichloro organic monomer as the other starting material has the general formula The α, α′-dichloro-xylene derivative represented by the following formula is used.

As the above-mentioned condensation catalyst, an alkali metal or magnesium which causes a condensation reaction by elimination of halogen is desirably used, and specific examples of the condensation catalyst include lithium, sodium, potassium, and magnesium. It is suitable.

The above-mentioned halogenated organic reagent is for introducing a substituent represented by A and A ', and comprises an alkyl halide compound, a cycloalkyl halide compound, an aryl halide compound and an aralkyl halide compound. A suitable compound selected from the group, i.e. the general formula: A
-X and / or general formula: A'-X (where X is Cl or Br)
And an appropriate compound in the specific examples described later is selectively used.

The above-mentioned halogenated silane is for introducing a substituent represented by A and A ', and a monohalogenated silane is used. That is, it is represented by the general formula: AX and / or the general formula: A'-X (where X is Cl or Br), and an appropriate compound in the specific examples described later is selectively used.

The general formula used in synthesizing the above-mentioned intermediate polymer: R ₁ R ₂ SiCl ₂ or a general formula: R ₃ R ₄ SiCl ₂ represented by dichlorosilane monomer and dichloro organic monomer,
When dissolved in a predetermined solvent and introduced into the reaction system, a paraffin-based nonpolar hydrocarbon solvent is desirably used as the solvent. Preferred examples of the solvent include n-hexane, n-octane, n-nonane, n-dodecane, cyclohexane and cyclooctane.

Since the resulting intermediate polymer 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 above-mentioned halogenated organic reagent. At this time, both are dissolved in the same solvent and used for the reaction. As the solvent in this case, an aromatic solvent such as benzene, toluene and xylene is preferably used.

In order to obtain the desired intermediate by condensing the above-mentioned dichlorosilane monomer and dichloroorganic monomer using the above-mentioned alkali metal or magnesium catalyst, polymerization of the intermediate polymer obtained by adjusting the reaction temperature and the reaction time is carried out. The degree can be controlled appropriately. However, the reaction temperature at that time is desirably set between 60 and 130 ° C.

One preferred embodiment of the method for producing the above-described polysilane copolymer represented by the general formula [I] of the present invention will be described below.

That is, the above-mentioned method for producing a polysilane copolymer according to the present invention comprises: (i) a step of producing an intermediate polymer; and (ii)
Introducing substituents A and A 'into the terminal of the intermediate polymer.

The step (i) is performed as follows. That is, the inside of the reaction system of the reaction vessel was completely removed of oxygen and moisture, maintained at a predetermined internal pressure controlled by argon, charged with an oxygen-free paraffin-based solvent and an oxygen-free condensation catalyst. A chlorosilane monomer and an oxygen-free dichloroorganic monomer are charged, and the whole is heated to a predetermined temperature while stirring to condense the monomer. At this time, the degree of condensation of the dichlorosilane monomer and the dichloroorganic monomer is controlled by controlling the reaction temperature and the reaction time so that an intermediate polymer having a desired degree of polymerization is produced.

In this reaction, the chloro group of the dichlorosilane monomer and the dichloroorganic monomer and the catalyst undergo a desalination reaction as shown by the following reaction formula (i), and the Si groups repeatedly condense to form a polymer. Produces a body polymer.

In a specific reaction procedure, a condensation catalyst (alkali metal or magnesium) is charged in a paraffinic solvent, and a dichlorosilane monomer and a dichloroorganic monomer are added dropwise while stirring under heating. The degree of polymerization is confirmed by sampling the reaction solution.

Simple confirmation of polymerization can be determined by volatilizing the sampling liquid to form a film. As the condensation proceeds and the polymer is formed, it becomes a white solid and precipitates from the reaction system. Here, the mixture is cooled, and the solvent containing the monomer is separated from the reaction system by decantation to obtain an intermediate polymer.

Next, the step (b) is performed. That is, the chloro group of the terminal group of the obtained intermediate polymer is desalted and condensed with a halogenated organic agent or a halogenated silane using a condensation catalyst (alkali metal or magnesium) to replace the polymer terminal group with a predetermined organic group. I do. When the terminal group is substituted with an alkoxy group, it can also be obtained by a method of dropping an intermediate polymer into alcohol, but the above method is preferable. The above reaction is represented by the following reaction formula.

Specifically, an aromatic solvent is added to and dissolved in the intermediate polymer obtained by condensation of dichlorosilane monomer and dichloroorganic monomer. Next, a condensation catalyst (alkali metal or magnesium) is added, and a halogenated organic agent is added dropwise at room temperature. At this time, a halogenated organic agent or a halogenated silane is added in an amount of 0.01 to 0.1 times the amount of the starting monomer in order to compete with the condensation reaction between the polymer terminal groups. The mixture is gradually heated, and heated and stirred at 80 to 100 ° C. for 1 hour to perform a desired reaction.

After the reaction, the mixture is cooled, and methanol is added to remove the alkali metal or magnesium of the catalyst. Next, the polysilane copolymer is extracted with toluene and purified with a silica gel column. Thus, the desired polysilane copolymer of the present invention is obtained.

Specific examples of R ₁ R ₂ SiCl ₂ and R ₃ R ₄ SiCl ₂ Note: a-2 to 16, 18, 20, 21, 23, and 24 in the following compounds
Is used for R ₁ R ₂ SiCl ₂ and a−1,2,11,17,19,22,23,25 is
Used for R ₃ R ₄ SiCl ₂ .

As the catalyst, an alkali metal is preferable.

As the alkali metal, lithium, sodium, and potassium are used. The shape is preferably a wire or a chip to increase the surface area.

Note): X, Y and Z in the above structural formulas all indicate weight units. And n is X / (X + Y + Z) or m is
Y / (X + Y + Z) and p are obtained by the formula of Z / (X + Y + Z).

〔Example〕

Hereinafter, the present invention will be described in more detail with reference to examples, but the present invention is not limited to these examples.

Example 1 A three-necked flask was prepared in a blow box in which vacuum suction and argon substitution were performed, and a reflux condenser, a thermometer, and a dropping funnel were attached thereto, and argon gas was passed through a bypass pipe of the dropping funnel. .

100 g of dehydrated dodecane and 0.3 mol of metal sodium wire were charged into the three-necked flask, and heated to 100 ° C. with stirring. Next, 0.05 mol of dichlorosilane monomer (manufactured by Chisso Corporation) (a-7) and 0.05 mol of α, α′-dichloro-p-xylene are dissolved in 30 g of dehydrated dodecane, and the prepared solution is slowly added to the reaction system. It was dropped.

After the addition, the mixture was condensed at 100 ° C. for 1 hour to precipitate a white solid. Thereafter, the mixture was cooled, decanted of dodecane, and further added with 100 g of dehydrated toluene to dissolve the white solid.
Mole was added. Next, a solution prepared by dissolving 0.01 mol of n-hexyl chloride (manufactured by Tokyo Kasei) (b-3) in 10 ml of toluene was slowly added dropwise to the reaction system with stirring, and the mixture was heated at 100 ° C. for 1 hour. Thereafter, the mixture was cooled, and 50 ml of methanol was slowly added dropwise to treat excess metal sodium. This produced a suspension layer and a toluene layer.

Next, the toluene layer was separated, concentrated under reduced pressure, and then developed and purified by silica gel column and chromatography to obtain polysilane copolymer No. 1. The yield was 45%.

The weight average molecular weight of this polysilane copolymer was 68,000 as measured by developing with THF by GPC (polystyrene as a standard).

For identification, IR produced KBr pellets and Nicolet FT-IR7
50 (manufactured by Nicolet Japan). Also, NM
R was measured by dissolving the sample in CDCl ₃ and using FT-NMR FX-90Q (manufactured by JEOL). The results are shown in Table 4.

In the polysilane copolymer obtained in the present invention, unreacted Si-Cl and dichloroorganic monomer by-product Si
There was no IR absorption attributed to -O-Si, Si-OR.

Examples 2 to 5 In Example 1, dichlorosilane monomer and α,
Synthesis was performed in the same manner as in Example 1 except that the amount of α'-dichloro-p-xylene was changed as shown in Table 1, to obtain polysilane copolymers Nos. 2 to 5. Table 4 shows the results of the identification.

Incidentally, in the polysilane copolymer obtained in the present invention, unreacted Si-Cl, dichloro organic monomer by-product
There was no IR absorption attributed to Si-O-Si or Si-OR.

Comparative Example 1 In Example 1, 0.1 mol of dichlorosilane monomer was charged, and synthesis was performed in the same manner as in Example 1 without adding α, α′-dichloro-p-xylene to obtain polysilane D-1. Table 4 shows the results of the identification.

In addition, unreacted in the obtained polysilane copolymer
There was no IR absorption attributed to Si-Cl, Si-O-Si or Si-OR as a by-product.

Example 6 A three-necked flask was prepared in a blow box in which vacuum suction and argon substitution were performed, and a reflux condenser, a thermometer, and a dropping funnel were attached thereto, and argon gas was passed through a bypass pipe of the dropping funnel. .

100 g of dehydrated n-hexane and 0.3 mol of 1 mm square metal sodium were charged into the three-necked flask, and heated to 80 ° C. with stirring. Next, a solution prepared by dissolving 0.05 mol of dichlorosilane monomer (manufactured by Chisso Corporation) (a-13) and 0.05 mol of α, α′-dichloro-p-xylene in dehydrated n-hexane is slowly added to the reaction system. It was dropped. After the dropping, condensation polymerization was carried out at 80 ° C. for 3 hours to precipitate a white solid. Thereafter, the mixture was cooled, n-hexane was decanted, and a white solid was dissolved by further adding 100 g of dehydrated toluene, and 0.02 mol of sodium metal was added. Next, trimethylchlorosilane (Nitrogen Co., Ltd.)
A solution prepared by dissolving 0.01 mol of (b-18) in 10 ml of toluene was slowly added dropwise to the reaction system with stirring, and heated at 80 ° C. for 1 hour. Thereafter, the mixture was cooled, and 50 ml of methanol was slowly added dropwise to treat excess metal sodium. This produced a suspension layer and a toluene layer.

Next, the toluene layer was separated, concentrated under reduced pressure, and developed and purified by silica gel column and chromatography to obtain polysilane copolymer No. 6. The yield was 38% and the weight average molecular weight was 69,000. The results of the identification are shown in Table 4.

In this polysilane copolymer, unreacted Si
-Cl, dichloro organic monomer by-product Si-O-Si, Si
There was no IR absorption attributed to -OR.

Examples 7 to 10 In Example 6, the dichlorosilane monomer and α,
Synthesis was performed in the same manner as in Example 6 except that the amount of α'-dichloro-p-xylene was changed to the amount shown in Table 2, to obtain polysilane copolymers Nos. 7 to 10. Table 4 shows the results of the identification.

Incidentally, in the polysilane copolymer obtained in the present invention, unreacted Si-Cl, dichloro organic monomer by-product
There was no IR absorption attributed to Si-O-Si or Si-OR.

Comparative Example 2 In Example 6, 0.1 mol of dichlorosilane monomer was charged, and synthesis was carried out in the same manner as in Example 6 without adding α, α'-dichloro-p-xylene to obtain polysilane D-2. Table 4 shows the results of the identification.

In addition, unreacted in the obtained polysilane copolymer
There was no IR absorption attributed to Si-Cl and the by-products Si-O-Si and Si-OR.

Examples 11 to 14 Synthesis was carried out in the same manner as in Example 1 using the dichlorosilane monomer, the dichloroorganic monomer and the terminal group treating material shown in Table 3.

Table 4 shows the yield, weight average molecular weight, IR and NMR data of the synthesized polysilane copolymer.

The copolymerization ratio of the silane monomer and the dichloro organic monomer was determined from the number of protons in NMR.

Comparative Example 3 Synthesis was performed in the same manner as in Example 1 using the dichlorosilane monomer and the terminal group-treated material shown in Table 3. Table 4 shows the yield, weight average molecular weight, IR and NMR data of the synthesized polysilane. The copolymerization ratio of the silane monomer was determined from the number of protons in NMR.

Use Example 1 An example in which the polysilane copolymer of the present invention was used as a resist material is shown below.

Phenol novolak resin (AZ-
B50J: Shipley Co.) was formed to a thickness of 2 μm by spin coating, and heated at 150 ° C. for 30 minutes. Next, 5 parts by weight of the polysilane copolymer No. 1 obtained in Example 1 was used,
0.5 parts by weight of p-hydroquinone was dissolved in toluene and applied by spin coating to form a 0.3 μm-thick polysilane layer, which was baked at 90 ° C. for 30 minutes to prepare a composite resist layer.

This is passed through a quartz mask with a line width of 0.2 μm and 0.5 μm
Ultraviolet light was irradiated for 30 seconds using a 0 W xenon-mercury lamp. It was immersed in a mixed solvent of toluene-isopropyl alcohol (weight ratio 1: 5) for 30 seconds, developed, and rinsed with isopropyl alcohol to obtain a positive resist pattern having a line width of 0.2 μm and 0.5 μm. Subsequently, oxygen plasma etching was performed, and the lower organic layer was dry-etched to form a 0.2 μm line width and 0.5 μm line width resist pattern having an aspect ratio of 2 or more.

The film forming ability of this polysilane copolymer and the development of the resist pattern were evaluated, and the results are shown in Table 5. Further, the adhesiveness of the composite resist layer was evaluated. With respect to the composite resist layer on which the above-mentioned polysilane layer is formed, 11 cutting streaks are formed every 1 mm, and 11 cutting streaks are similarly formed vertically to form 100 base lines. Cellophane tape (manufactured by Nichiban) was adhered to the base, and the number of bases that were not peeled off and peeled was counted to obtain a measured value.

Use Examples 2 to 17 The polysilane copolymers used in Use Example 1 were Nos. 2 to
14, and a resist pattern was formed and evaluated in exactly the same manner except that D-1 to D-3 were replaced. The results are shown in Table 5.

[Summary of Effects of the Invention] As described above, the polysilane copolymer of the present invention is:
It is synthesized by subjecting a dichlorosilane monomer and a dichloroorganic monomer to halogen desorption and condensation polymerization, and further desalting and condensing the terminal group of the polysilane copolymer with a halogenated organic group and an alkali metal. Yes, excellent in solubility and film forming ability.

Continuation of the front page (72) Inventor Hisami Tanaka 3-30-2 Shimomaruko, Ota-ku, Tokyo Canon Inc. (56) References JP-A-60-12545 (JP, A) JP-A-60-61744 ( JP, A) JP-A-2-212522 (JP, A) (58) Fields investigated (Int. Cl. ⁷ , DB name) C08G 77/60

Claims (4)

(57) [Claims] 1. A polysilane copolymer represented by the general formula [I]. Wherein R ₁ is an alkyl group having 1 or 2 carbon atoms, R ₂ is an alkyl group having 3 to 8 carbon atoms, a cycloalkyl group, an aryl group or an aralkyl group, and R ₃ is an alkyl group having 1 to 4 carbon atoms. R ₄ represents an alkyl group having 1 to ₄ carbon atoms, and R ₅ represents a hydrogen atom or a methyl group. A and A 'each represent an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group or a substituted silyl group having 4 to 12 carbon atoms, which may be the same or different. n, m, and p are molar ratios indicating the ratio of the number of each monomer to the total monomers in the polymer, and n + m + p = 1, and 0 <
n <1, 0 ≦ m <1, 0 <p <1. Q represents 0 or 1. ] 2. A dichlorosilane monomer and a dichloroorganic monomer represented by the following general formula (1) are brought into contact with a condensation catalyst comprising an alkali metal or magnesium in a high-purity inert atmosphere free of oxygen and moisture. Halogen elimination and polycondensation are performed to synthesize an intermediate polymer, the obtained polymer is separated from unreacted monomers, and the polymer is converted into a halogenated compound represented by the following general formula (2) or (3). An organic reagent is reacted in the presence of a condensation catalyst comprising an alkali metal or magnesium to condense an organic group to the terminal of the polymer, and is represented by the general formula [I] according to claim (1). A method for producing a polysilane copolymer. [Wherein, Q represents 0 or 1. A and A 'each represent an alkyl group having 4 to 12 carbon atoms, a cycloalkyl group, an aryl group, an aralkyl group or a substituted silyl group, which may be the same or different. X is a chlorine atom or a bromine atom. ] 3. The polysilane copolymer represented by the general formula [I] according to claim 1, which is obtained by the production method according to claim 2. 4. A resist material comprising the polysilane copolymer represented by the general formula [I] according to claim 1, obtained by the production method according to claim 2.