JPH04218533A - Silane derivative, polysilane compound, their production and use - Google Patents

Abstract

PURPOSE:To obtain a new bis(halogen-substituted thienyl)silane derivative capable of readily providing a new polysilane compound useful as an electrically conductive material due to excellent electric conductivity with good reproducibility. CONSTITUTION:A bis(5-halogen-substituted thienyl) silane derivative expressed by formula I (R and R<2> are alkyl, aryl, etc.; R<3> to R<6> are H, alkyl, etc.; X and X<2> are halogen; m is >=1), e.g. bis [(5-bromothienyl)]dimethylsilane. The aforementioned compound is obtained by reacting a compound expressed by formula II (R<7> and R<8> are H, alkoxy, etc.; X<3> and X<4> are halogen) with Mg in a solvent such as diethyl ether while cooling the reaction mixture with ice, providing a 2-halogen-substituted-5-halogen magnesium thiophene derivative, then adding a compound expressed by formula III at ordinary temperature and subsequently carrying out reaction while stirring and heating the mixture. Furthermore, the new polysilane compound is obtained by reacting the compound expressed by formula I with Mg and then polymerizing the resultant product in the presence of a transition metallic complex catalyst.

Description

[Detailed description of the invention]

0001

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to novel and useful silane derivatives and polysilane compounds, methods for their production, and conductive materials made of these polysilane compounds.

0002

2. Description of the Related Art Hitherto, metals have been used exclusively as materials requiring electrical conductivity, and organic polymer compounds have generally been treated as insulating materials. However, in recent years, it has been discovered that among organic polymer compounds that were recognized as insulating materials, those containing silicon atoms have electrical conductivity. Attempts are being made to use it as a

For example, in 1981, methylphenylpolysilane, a type of polysilane, was irradiated with light to obtain a compound with a crosslinked structure, and by adding a dopant (doping agent) to this, a compound with high electrical conductivity was created. It has been found that this can be obtained. A compound such as AsF5 is used as the dopant, and it is disclosed that by using such a dopant, the silicon-containing compound exhibits a conductivity of about 0.5 S/cm (J. Amer.Chem.Soc
．． , 103, 7352-7354 (1981)).

However, in order to use the above silicon-containing compound as a conductive material, highly toxic AsF5 must be used as a dopant. Furthermore, when producing the silicon-containing compounds as described above, there are also problems in that it is difficult to control light irradiation and it is difficult to produce compounds with good properties with good reproducibility.

[0005] Furthermore, JP-A-62-59632 discloses a matrix-like polyalkylsilane that exhibits excellent conductivity without using AsF5. It has been shown here that by incorporating sulfate ions as a dopant into polyalkylsilane, polyalkylsilane has an electrical conductivity of about 10-5 to 10 S/cm.

However, even in the conductive material made of polyalkylsilane as described above, there is still room for improvement in characteristics such as conductivity and manufacturing method.

[0007]

SUMMARY OF THE INVENTION An object of the present invention is to provide new and useful silane derivatives and polysilane compounds. Another object of the present invention is to propose a manufacturing method for easily and efficiently manufacturing the above-mentioned silane derivatives and polysilane compounds. Another object of the present invention is to provide a conductive material made of the above polysilane compound that exhibits excellent conductivity, has good reproducibility, and is easy to manufacture.

[0008]

[Means for Solving the Problems] The present invention provides the following silane derivatives and polysilane compounds, methods for producing them, and conductive materials comprising the polysilane compounds.

(1) General formula [1]

embedded image (wherein R and R2 each independently represent a group selected from the group consisting of an alkyl group, an aryl group, an aralkyl group, an alkylsilyl group, and an arylsilyl group, R3,
R4, R5 and R6 each independently represent a hydrogen atom or a group selected from the group consisting of an alkyl group, an aryl group, an aralkyl group and an alkoxy group, and X and X2
each independently represents a halogen atom, and m represents a number of 1 or more. ) A bis(5-halogen-substituted thienyl)silane derivative. (2) General formula [2]

embedded image (wherein R and R2 each independently represent a group selected from the group consisting of an alkyl group, an aryl group, an aralkyl group, an alkylsilyl group, and an arylsilyl group, R3,
R4, R5 and R6 each independently represent a hydrogen atom or a group selected from the group consisting of an alkyl group, an aryl group, an aralkyl group and an alkoxy group, and X and X2
each independently represents a halogen atom, and m represents a number of 1 or more. ) Bis(5-halogenmagnesiumthienyl)silane derivative. (3) General formula [3]

embedded image (wherein R and R2 each independently represent a group selected from the group consisting of an alkyl group, an aryl group, an aralkyl group, an alkylsilyl group, and an arylsilyl group, R3,
R4, R5 and R6 each independently represent a hydrogen atom or a group selected from the group consisting of an alkyl group, an aryl group, an aralkyl group and an alkoxy group, m represents a number of 1 or more, and n represents a number of 2 or more. show. ) A polysilane compound represented by (4) General formula [4]

(In the formula, R7 and R8 each independently represent a hydrogen atom or a group selected from the group consisting of an alkyl group, an aryl group, an aralkyl group, and an alkoxy group, and X3 and X4 each independently represent a halogen atom. 2-halogen-substituted-5- obtained by reacting the 2,5-dihalogen-substituted thiophene derivative represented by ) with magnesium.
2-2, which is obtained by reacting a halogen magnesium thiophene derivative or a 2,5-dihalogen-substituted thiophene derivative represented by the general formula [4] with a lithiation reagent.
The halogen-substituted 5-lithium thiophene derivative has the general formula [5]

embedded image (wherein R and R2 each independently represent a group selected from the group consisting of an alkyl group, an aryl group, an aralkyl group, an alkylsilyl group, and an arylsilyl group, and X5 and X6 each independently represent a halogen atom) and m is 1
Indicates the above number. ) A method for producing a bis(5-halogen-substituted thienyl)silane derivative represented by the general formula [1], which comprises reacting a dihalogen-substituted silane represented by the formula [1]. (5) Bis(5-halogenmagnesium thienyl) represented by the general formula [2], which is produced by reacting a bis(5-halogen-substituted thienyl)silane derivative represented by the general formula [1] with magnesium. A method for producing a silane derivative. (6) A bis(5-halogen magnesium thienyl) silane derivative obtained by reacting a bis(5-halogen-substituted thienyl) silane derivative represented by the general formula [1] with magnesium in the presence of a transition metal complex catalyst. A method for producing a polysilane compound represented by the general formula [3], which comprises polymerizing the polysilane compound. (7) A conductive material whose main chain is composed of a polysilane compound having a repeating unit of silanylene dithienylene unit represented by the general formula [3].

R and R2 in the general formulas [1] to [3]
is a group selected from the group consisting of an alkyl group, an aryl group, an aralkyl group, an alkylsilyl group, and an arylsilyl group, and R and R2 may be the same or different.

R and R2 in the general formulas [1] to [3]
The alkyl group represented by usually has 1 to 6 carbon atoms,
Preferably, 1 to 3 can be mentioned. The alkyl group may be linear or branched. Specifically, such alkyl groups include linear alkyl groups such as methyl group, ethyl group, n-propyl group, and n-butyl group; isopropyl group, sec-butyl group, sec-
Secondary alkyl group such as amyl group; tert-butyl group, t
Examples include tertiary alkyl groups such as ert-amyl groups.

R and R2 in the general formulas [1] to [3]
Examples of the aryl group represented by the above include monovalent aryl groups having at least one aromatic ring. This aromatic ring may have a substituent. Specific examples of such aryl groups include phenyl, naphthyl, tolyl, and xylyl groups.

R and R2 in the general formulas [1] to [3]
Examples of the aralkyl group represented by the above include monovalent aralkyl groups in which an aliphatic hydrocarbon is substituted with at least one aromatic ring. This aromatic ring may have a substituent. Specific examples of such aralkyl groups include benzyl group, phenethyl group, α-methylbenzyl group, and tolylmethyl group.

R and R2 in the general formulas [1] to [3]
Examples of the alkylsilyl group represented by the formula include monovalent alkylsilyl groups having at least one alkyl group. This alkyl group has 1 to 1 carbon atoms.
8, preferably 1 to 6. The alkyl group may be linear or branched. Specific examples of such alkylsilyl groups include linear alkylsilyl groups such as methylsilyl group, ethylsilyl group, n-propylsilyl group, and n-butylsilyl group; isopropylsilyl group, sec-butylsilyl group,
Secondary alkylsilyl group such as sec-amylsilyl group; t
Examples include tertiary alkylsilyl groups such as ert-butylsilyl group and tert-amylsilyl group.

R and R2 in the above general formulas [1] to [3]
Examples of the arylsilyl group represented by include monovalent arylsilyl groups having at least one aromatic ring. This aromatic ring may have a substituent. Specific examples of such arylsilyl groups include:
Examples include phenylsilyl group, naphthylsilyl group, tolylsilyl group, and xylylsilyl group.

When the polysilane compound of the present invention represented by the general formula [3] is used as a conductive material, R and R2 are a methyl group, an ethyl group, a phenyl group, a benzyl group, a methylsilyl group, an ethylsilyl group, and a phenylsilyl group. A combination of groups selected from the group consisting of groups is preferred;
Particularly preferred are combinations of methyl groups, combinations of methyl groups and phenyl groups, and combinations of methyl groups and trimethylsilyl groups.

R3 to R6 in the general formulas [1] to [3] are hydrogen atoms, or groups selected from the group consisting of alkyl groups, aryl groups, aralkyl groups, and alkoxy groups, and R3 to R6 may be the same or the same. May be different.

The alkyl groups represented by R3 to R6 in the above general formulas [1] to [3] usually have 1 to 8 carbon atoms, preferably 1 to 6 carbon atoms. The alkyl group may be linear or branched. Specific examples of such alkyl groups include linear alkyl groups such as methyl, ethyl, n-propyl, and n-butyl groups; alkyl group; tert-butyl group, te
Examples include tertiary alkyl groups such as rt-amyl group.

The aryl groups represented by R3 to R6 in the general formulas [1] to [3] include monovalent aryl groups having at least one aromatic ring. This aromatic ring may have a substituent. Specific examples of such aryl groups include phenyl groups,
Examples include naphthyl group, tolyl group, and xylyl group.

The aralkyl groups represented by R3 to R6 in the general formulas [1] to [3] include monovalent aralkyl groups in which an aliphatic hydrocarbon is substituted with at least one aromatic ring. This aromatic ring may have a substituent. Specific examples of such aralkyl groups include benzyl group, phenethyl group, α-methylbenzyl group, and tolylmethyl group.

The alkoxy groups represented by R3 to R6 in the general formulas [1] to [3] usually have 1 to 8 carbon atoms,
Preferably, 1 to 6 can be mentioned. The alkoxy group may be linear or branched. Specific examples of such alkoxy groups include linear alkoxy groups such as methoxy, ethoxy, n-propoxy, and n-butoxy; isopropoxy, sec-butoxy, and sec-amyloxy groups; Secondary alkoxy groups; examples include tertiary alkoxy groups such as tert-butoxy and tert-amyloxy groups.

When the polysilane compound of the present invention represented by the general formula [3] is used as a conductive material, R3
~R6 is a hydrogen atom, a methyl group, an ethyl group, a phenyl group,
A combination selected from the group consisting of benzyl group and methoxy group is preferred.

In the general formula [3], m is a number of 1 or more, and n is a number of 2 or more. When the polysilane compound of the present invention is used as a conductive material, it is desirable that m is 1 or more, n is 10 or more, and the average molecular weight is 1000 or more, preferably 3000 or more.

The halogen atoms represented by X and X2 in the general formulas [1] and [2] include fluorine, chlorine,
Examples include bromine and iodine. The general formula [
1] or the bis(5-halogen-substituted thienyl)silane derivative represented by the general formula [2].
5-halogen magnesium thienyl) silane derivative,
When used as a raw material for producing a polysilane compound represented by the general formula [3], X and X2 are preferably chlorine or bromine.

Bis(5-
Specific examples of halogen-substituted thienyl)silane derivatives include bis(5-halogen-substituted thienyl)dimethylsilane, bis(5-halogen-substituted thienyl)methylethylsilane, and bis(5-halogen-substituted thienyl)silane, where m is 1. Methylphenylsilane, bis(5-halogen-substituted thienyl)methyltolylsilane, bis(5-halogen-substituted-4-methylthienyl)methylphenylsilane, bis(5-halogen-substituted thienyl)methyltrimethylsilylsilane, etc., where m is 2. 1,2-bis(5
-halogen-substituted thienyl)tetramethyldisilane, 1,
2-bis(5-halogen-substituted thienyl)dimethyldiethyldisilane, 1,2-bis(5-halogen-substituted thienyl)dimethyldiphenyldisilane, 1,2-bis(5-halogen-substituted thienyl)dimethylditolyldisilane, 1,
2-bis(5-halogen-substituted-3-methylthienyl)dimethyldiphenyldisilane, etc., where m is 3 or more, 1,3-bis(5-halogen-substituted thienyl)hexamethyltrisilane, 1,3-bis( 5-halogen substituted thienyl)triethyltrimethyltrisilane, 1,3-bis(5-halogen substituted thienyl)trimethyltriphenyltrisilane, 1,3-bis(5-halogen substituted thienyl)trimethyltri(tolyl)trisilane, 1, Examples include 3-bis(5-halogen-substituted-4-methylthienyl)trimethyltriphenyltrisilane. Examples of the halogen in these compounds include bromine and chlorine.

Bis(5-
The halogen-substituted thienyl)silane derivative is obtained by reacting, for example, the 2,5-dihalogen-substituted thiophene derivative represented by the general formula [4] with magnesium.
It can be produced by reacting a halogen-substituted 5-halogen magnesium thiophene derivative with a dihalogen-substituted silane represented by the general formula [5]. As another method, a 2-halogen-substituted-5-lithium thiophene derivative obtained by reacting a 2,5-dihalogen-substituted thiophene derivative represented by the general formula [4] with a lithiation reagent is added to a 2-halogen-substituted-5-lithium thiophene derivative represented by the general formula [4]. It can also be produced by reacting dihalogen-substituted silanes represented by [5]. Examples of the lithiation reagent include organic lithium compounds such as butyllithium.

Bis(5-
A preferred method for producing the halogen-substituted thienyl)silane derivative is to react the 2,5-dihalogen-substituted thiophene derivative represented by the general formula [4] with magnesium in a solvent such as diethyl ether under ice cooling. An example of a method is to synthesize a -halogen-substituted-5-halogen magnesium thiophene derivative, then add a dihalogen-substituted silane represented by the general formula [5] at room temperature, and then react with stirring while heating. can.

Another preferable production method is to cool the 2,5-dihalogen-substituted thiophene derivative represented by the general formula [4], dropwise add a hexane solution of tert-butyllithium, and then stir at room temperature. A 2-halogen-substituted-5-lithium thiophene derivative is synthesized by reacting while stirring, and then a dihalogen-substituted silane represented by the general formula [5] is added at room temperature, and the reaction is carried out while stirring while heating. I can give you a method. In either production method, after the reaction is completed, the target bis(5-halogen-substituted thienyl)silane A derivative is obtained.

As the alkyl group, aryl group, aralkyl group or alkoxy group represented by R7 and R8 in the above general formula [4], the same groups as in the above general formula [1] can be mentioned. Also, R and R2 in the general formula [5]
Examples of the alkyl group, aryl group, aralkyl group, alkylsilyl group, or arylsilyl group represented by are the same as those in the general formula [1] above. X3~
Examples of the halogen atom for X6 include fluorine, chlorine, bromine, and iodine.

Bis(5-
The halogen magnesium thienyl) silane derivative can be produced, for example, by reacting the bis(5-halogen substituted thienyl) silane derivative represented by the general formula [1] with magnesium. In this reaction, it is preferable to use magnesium in an amount such that it reacts with at least the halogen atom in the bis(5-halogen-substituted thienyl)silane derivative [1];
It is desirable to use it in an amount of 0.8 to 1.2 mol, preferably 0.9 to 1.1 mol, per 1 mol of the halogen-substituted thienyl)silane derivative [1].

The reaction between the bis(5-halogen-substituted thienyl)silane derivative [1] and magnesium is usually carried out as a liquid phase reaction using a solvent. As a solvent, it has no reactivity towards magnesium and is inert.
It is preferable to use a solvent that is also inert to the bis(5-halogen-substituted thienyl)silane derivative [1] as a raw material. Furthermore, it is preferable to use a solvent that is also inert to the transition metal complex catalyst described below. Examples of such solvents include aromatic hydrocarbon solvents, saturated hydrocarbon solvents, unsaturated hydrocarbon solvents, and ether solvents. Among these, tetrahydrofuran, diethyl ether, dibutyl ether, dioxane,
Ether solvents such as 2-methoxyethyl ether are preferred, and tetrahydrofuran is particularly preferred. These solvents can be used alone or in combination of two or more.

[0032] The reaction temperature is usually -20 to 100°C.
, preferably at a temperature in the range of 0 to 50°C. The reaction can also be carried out under reduced pressure or increased pressure.
The reaction pressure is not limited, but is usually reduced pressure to 60 kg/
cm2·G, preferably 0 to 30 kg/cm2·G. The reaction time is appropriately set in consideration of reaction temperature, reaction pressure, etc., and is usually 5 minutes to 100 hours, preferably 1 to 20 hours. Further, the reaction is usually preferably carried out under an inert atmosphere. As the inert atmosphere, for example, argon or nitrogen atmosphere is used.

Bis(5-halogen-substituted thienyl)silane derivative [1] and bis(5-halogen-substituted thienyl)silane derivative [1] obtained as described above.
-Halogen magnesium thienyl) silane derivative [2]
is used as a raw material or intermediate for producing the polysilane compound represented by the general formula [3].

[0034] The polysilane compound represented by the general formula [3] is, for example, a bis(
Bis(5-halogenmagnesiumthienyl)silane derivative [2] obtained by reacting a 5-halogen-substituted thienyl)silane derivative with magnesium can be produced by polymerizing it in the presence of a transition metal complex catalyst.

When the polysilane compound of the present invention is used as a conductive material, bis(5-halogen-substituted thienyl)
As the silane derivative [1], particularly bis(5-bromothienyl)dimethylsilane, bis(5-bromothienyl)
Methylphenylsilane, bis(5-bromothienyl)methyltrimethylsilane, 1,2-bis(5-bromothienyl)tetramethyldisilane, 1,2-bis(5-bromothienyl)dimethyldiphenyldisilane or 1,3
-Bis(5-bromothienyl)hexamethylsilane is preferably used.

[0036] The bis(5-halogen-substituted thienyl)silane derivative [1] is usually used alone, but two or more types may be combined for the purpose of, for example, adjusting the conductivity of the resulting polysilane compound. It can also be used.

As the transition metal complex catalyst, for example, a nickel complex used in a cross-coupling reaction between a Grignard reagent and an organic halide can be used, and specifically, dichloro(2,2'-bipyridine) nickel can be used. , dichlorobis(triphenylphosphine)nickel, dichloro(1,2-bisdiphenylphosphinoethane)nickel, and dichloro(1,2-bisdimethylphosphinoethane)nickel. Further examples include nickel bipyridyl chloride, nickel chloride (diphenylphosphinoethane), palladium chloride and palladium acetate. Among these, dichloro(2,2'-bipyridine)nickel or nickel chloride (diphenylphosphinoethane) is preferably used.

The transition metal complex catalyst is used in an amount of 1× per mole of bis(5-halogen-substituted thienyl)silane derivative [1].
10-4 to 1 x 10-2 mol, preferably 2 x 10-4
It is desirable to use it in a range of 1 x 10-3 mol. One type of transition metal complex catalyst can be used alone, or
A mixture of two or more types can also be used.

Examples of reactions related to the production of the polysilane compound of the present invention are shown below.

embedded image (In the formula, R to R6, m and n are the same as in the general formula [3] above.)

According to the reaction mechanism of the above general formula [6],
The polysilane compound represented by the general formula [3] can be represented by the following general formula [7] or [8], which are substantially the same when viewed as a polymer.

[0041]

[Chemical formula 18]

embedded image (In the formula, R to R6, m and n are the same as in the above general formula [3]. p and q are numbers satisfying p+q=m.)

The polysilane compound of the present invention can be prepared by, for example, producing the bis(5-halogen-substituted thienyl)silane derivative [1] and magnesium in the same manner as the method for producing the bis(5-halogenmagneusimthienyl)silane derivative [2]. The bis(5-halogenmagnesiumthienyl)silane derivative [2] can be produced by adding the transition metal complex catalyst to the reaction solution and polymerizing it without separating the bis(5-halogenmagnesiumthienyl)silane derivative [2] from the reaction solution.

[0043] In the polymerization reaction, the reaction temperature is usually -20 to -25
It is desirable to carry out at 0°C, preferably in the range of 0 to 230°C. Further, the polymerization reaction can be carried out under reduced pressure or increased pressure, and the reaction pressure is not limited, but it is usually reduced pressure to 6°C.
0 kg/cm2・G, preferably 0 to 30 kg/cm2
-G, particularly preferably in the range of 0 to 5 kg/cm2.G. The reaction time is appropriately set in consideration of the reaction temperature, reaction pressure, etc., and is usually 5 minutes to 150 hours, preferably 1 to 100 hours.

[0044] The polymerization reaction can also be carried out while irradiating with ultrasonic waves. In this case, the reaction temperature is usually -20 to 250℃
, preferably 0 to 230°C, reaction time usually 5 minutes to 50
time, preferably 1 to 20 hours, reaction pressure usually 0 to 3
0 kg/cm2・G, preferably 0 to 5 kg/cm2・
G is preferable. Further, the polymerization reaction is usually preferably carried out under an inert atmosphere. As the inert atmosphere, for example, argon or nitrogen atmosphere is used.

The polysilane compound thus produced has repeating units represented by the above general formula [3], and terminal groups derived from the raw materials used and the reaction of the above general formula [6]. has. The terminal group is thought to be hydrogen or halogen, but many are uncertain.

After the reaction is completed, a polysilane compound can be obtained by distilling off the solvent and adding chloroform and a solvent such as ethanol or isopropanol for reprecipitation.

In this way, the polysilane compound represented by the general formula [3] obtained by the present invention usually has a conductivity σ of 10 −8 S/cm or less, but by adding a dopant, the conductivity can be increased. σ is usually 0.01 to 5
It will be about 0S/cm. Therefore, the polysilane compound of the present invention can be used as a conductive material.

The reason why the polysilane compound of the present invention exhibits electrical conductivity is not clear, but it is presumed that it is because it has both a silicon-silicon bond and a thiophene ring.

The polysilane compound of the present invention exhibits better electrical conductivity by adding a dopant. Therefore, when the polysilane compound of the present invention is used as a conductive material, it is generally used with the addition of an appropriate dopant. The dopant is not particularly limited, and conventionally known halogens; Lewis acids; electron-withdrawing compounds such as transition metal halides; and electron-donating compounds such as alkali metals can be used. Specific dopants include, for example, I2, SO3, AsF.
5, SbF5, SbCl5, etc. Among these, SbF5 is preferred. These dopants can be used alone or in combination of two or more.

The method of adding a dopant to a polysilane compound is not particularly limited, and examples include a method of molding a polysilane compound into an arbitrary shape, such as a film shape, and then applying a dopant to the molded product, a method of adding a dopant to the molded product, and a method of adding a dopant to the molded product. Various methods can be employed, such as a method in which a dopant is added to a polysilane compound and then molded into an arbitrary shape. The molding method and the shape of the molded body at this time are not particularly limited, and depending on the shape of the intended conductive material, it can be molded into any shape such as a film shape or a linear shape by a known method.

The polysilane compound of the present invention can be used not only as a conductive material as described above, but also as a photosensitive material by utilizing the optical functionality of the silicon-silicon bond or the silicon-aromatic carbon bond. be able to.

[0052]

As described above, according to the present invention, there are provided a novel and useful silane derivative represented by the general formula [1], a new and useful silane derivative represented by the general formula [2], and a novel and useful silane derivative represented by the general formula [2]. A novel and useful polysilane compound represented by formula [3] is obtained. The silane derivative represented by the general formula [1] is a 2-halogen-substituted-5- silane derivative obtained by reacting the 2,5-dihalogen-substituted thiophene derivative represented by the general formula [4] with magnesium or a lithiation reagent. It can be easily and efficiently produced by reacting a halogen magnesium thiophene derivative or a 2-halogen-substituted-5-lithium thiophene derivative with a dihalogen-substituted silane represented by the general formula [5]. The silane derivative represented by the general formula [2] is a bis(
It can be easily and efficiently produced by reacting a 5-halogen-substituted thienyl)silane derivative with magnesium. The polysilane compound represented by the general formula [3] is a bis(5) compound represented by the general formula [1].
- A bis(5-halogenmagnesiumthienyl)silane derivative obtained by reacting a halogen-substituted thienyl)silane derivative with magnesium can be easily and efficiently produced by polymerizing it in the presence of a transition metal complex catalyst. can. Further, according to the present invention, a conductive material exhibiting excellent conductivity can be easily obtained with good reproducibility.

[0053]

EXAMPLES Next, the present invention will be explained with reference to Examples, but the present invention is not limited to these Examples in any way.

Example 1 {Synthesis of bis[2-(5-bromothienyl)]dimethylsilane} 20 ml of ether was placed in a 50 ml eggplant-shaped flask.
and 10.0 g (41.3 m
mol) was added. This was cooled to -80℃ and ter
t-Butyllithium-hexane solution (1.7M) 25.
0 ml (42.5 mmol) was added dropwise over 1 hour, and the temperature was slowly returned to room temperature. After stirring for an additional 12 hours at room temperature, 2.6 g (20.0 m
mol) was added dropwise, and the mixture was refluxed for 3 hours.

After hydrolysis, the oil layer was separated, washed with water, extracted with hexane, and the oil layers were combined and dried over anhydrous magnesium sulfate. Thereafter, the solvent was distilled off, vacuum distillation (0.1°C/0.1mmHg) was performed, and further purification was performed using a column (silica gel, hexane).
bromothienyl)]dimethylsilane 5.5g (14.4
mmol, yield 72%). The boiling point of this compound is 1
The temperature was 15° C./0.1 mmHg, and the results of instrumental analysis are shown below.

1H nuclear magnetic resonance spectrum (measured in CDCl3 solvent, δppm) 0.49 (s, 6H, Si
CH3), 6.94(d,2H,ring
protons, J=4Hz), 6.
99 (d, 2H, ring protons, J=4
Hz) 13C nuclear magnetic resonance spectrum (measured in CDCl3 solvent, δppm) -0.6,118
．． 2,131.4,135.9,139.6 Mass spectrum m/e: 380 (M+) Elemental analysis (as C10H10Si1S2Br2)
Actual value C: 31.24, H: 2.70
Calculated value C: 31.43, H: 2.64

Example 2 {Polymerization of bis[2-(5-bromothienyl)]dimethylsilane} The bottom of a Pyrex tube with a branched length of 15 cm and an inner diameter of 10 mm was sealed, and a micro rotor and a magnesium 24.
3 mg (1.0 mmol) was added and heated under vacuum to dry. Then add 2 ml of tetrahydrofuran and 1,1-
Bis[2-(5-bromothienyl)]dimethylsilane 3
82 mg (1.0 mmol) was added and heated to 50°C to prepare a Grignard reagent. After cooling, 6.9 mg (0.013 mmol, 1.3 mol) of nickel dichloride (1,2-bisdiphenylphosphinoethane) was extracted from the branch.
%), the tube was degassed and sealed, and heated at 230°C for 100 hours.

After completion of the reaction, hydrolysis was carried out, extraction with chloroform, insoluble components were filtered, reprecipitation was carried out with chloroform/ethanol, and 175 mg (0.79 m
mol units) of poly[(dimethylsilylene)
-2,2'-bithienylene] was obtained in a yield of 79%. The melting point of this polymer is 168-172°C/0.1 mmHg, and the weight average molecular weight (Mw) obtained by GPC
was 7,800. The results of the instrumental analysis are shown below.

1H nuclear magnetic resonance spectrum (measured in CDCl3 solvent, δppm) 0.63 (s, 6H, Si
CH3), 7.20(s,4H,ring
protons) 13C nuclear magnetic resonance spectrum (measured in CDCl3 solvent, δppm) -
2.7, 125.4, 133.9, 134.4, 140
．． 8 Elemental analysis [as (C10H10Si1S2)n] Actual value C: 53.00, H:
4.45 Calculated value C: 53.06,
H:4.45

Example 3 {Synthesis of bis[2-(5-bromothienyl)]methylphenylsilane} Ether 2 was placed in a 50 ml eggplant-shaped flask.
0 ml and 10.0 g of 2,5-dibromothiophene (41
．． 3 mmol) was added. Cool this to -80℃,
tert-butyllithium-hexane solution (1.7M)
25.0 ml (42.5 mmol) was dropped over 1 hour,
The temperature was then slowly returned to room temperature. After stirring for a further 12 hours at room temperature, 3.8 g of dichloromethylphenylsilane
(20.0 mmol) was added dropwise and refluxed for 3 hours.

After hydrolysis, the oil layer was separated, washed with water, extracted with hexane, and the oil layers were combined and dried over anhydrous magnesium sulfate. Thereafter, the solvent was distilled off, vacuum distillation (155°C/0.1 mmHg) was performed, and further purification was performed using a column (silica gel, hexane).
bromothienyl)] methylphenylsilane 4.2g (9
．． 5 mmol, yield 47%). The boiling point of this compound is 155° C./0.1 mmHg, and the results of instrumental analysis are shown below.

1H nuclear magnetic resonance spectrum (measured in CDCl3 solvent, δppm) 0.84 (s, 2H, Si
CH3), 7.04(d,2H,Thie
nyl ring protons, J=4Hz)
, 7.11(d,2H,Thienyl
ring protons, J=4Hz), 7.34-7.57(m, 5H, Phen
yl ring protons) 13C nuclear magnetic resonance spectrum (measured in CDCl3 solvent, δppm) -1.6,119.0,
128.2, 130.4, 131.5, 1
34.1, 134.6, 137.5, 137.7 Mass spectrum m/e: 422 (M+) Elemental analysis (as C15H12Si1S2Br2)
Actual measurement value C: 40.66, H: 2.
90 Calculated value C: 40.55, H:
2.72

Example 4 {Polymerization of bis[2-(5-bromothienyl)]methylphenylsilane} The bottom of a Pyrex tube with a branched length of 15 cm and an inner diameter of 10 mm was sealed, and a micro rotor and 24.3 mg of magnesium ( 1.0 mmol) and heated and dried under vacuum. Then add 2 ml of tetrahydrofuran and 1
, 444 mg (1.0 mmol) of 1-bis[2-(5-bromothienyl)]methylphenylsilane were added, and 50
A Grignard reagent was prepared by heating to . After cooling, 6.9 mg (0.013 mmol) of nickel dichloride (1,2-bisdiphenylphosphinoethane) was extracted from the branch.
1.3 mol%), degassed and sealed the tube, and heated at 230℃ for 50 minutes.
heated for an hour.

After completion of the reaction, hydrolysis was carried out, extraction with chloroform, insoluble components were filtered, reprecipitation was carried out with chloroform/ethanol, and 280 mg (0.99 m
mol units) of poly[(methylphenylsilylene)-2,2'-bithienylene] was obtained in a yield of 99%. The melting point of this polymer is 148-155℃/0.1mmH
g, and the weight average molecular weight (M
w) was 30,000. The results of the instrumental analysis are shown below.

1H nuclear magnetic resonance spectrum (measured in CDCl3 solvent, δppm) 0.87 (s, 3H, Si
CH3), 7.18-7.61 (m, 9H
, ring protons) 13C nuclear magnetic resonance spectrum (measured in CDCl3 solvent, δppm)
-1.4, 125.6, 130.1, 134.
7,134.9, 135.0, 137.8
, 143.9 Elemental analysis [(C15H12Si1S2
) as n] Actual measurement value C: 63.24,
H: 4.38 Calculated value C: 63.3
3, H: 4.25

Example 5 {Synthesis of 1,1-bis[2-(5-bromothienyl)]tetramethyldisilane} 20 ml of ether and 5.4 g of 2,5-dibromothiophene were placed in a 50 ml eggplant-shaped flask.
(22.3 mmol) was added. This was cooled to -80°C, and a tert-butyllithium-hexane solution (1.
7M) was added dropwise over 1 hour, and the temperature was slowly returned to room temperature. After further stirring at room temperature for 12 hours, 2.1 g (11.2 mmol) of 1,1-dichlorotetramethyldisilane was added dropwise, and the mixture was refluxed for 3 hours.

After hydrolysis, the oil layer was separated, washed with water, and the aqueous layer was extracted with hexane. Thereafter, the oil layers were combined and dried over anhydrous magnesium sulfate, and the solvent was distilled off. Subsequently, the 1,1-
3.7 g (8.4 mmol, yield 75%) of bis[2-(5-bromothienyl)]tetramethyldisilane was obtained. The results of the instrumental analysis are shown below.

1H nuclear magnetic resonance spectrum (measured in CDCl3 solvent, δppm) 0.20 (s, 9H, Si
CH3), 0.63(s,3H,SiCH
3), 7.02(d,2H,ring
protons, J=4Hz), 7.11
(d, 2H, ring protons, J=4Hz
) 13C nuclear magnetic resonance spectrum (measured in CDCl3 solvent, δppm) -3.1, -2.2,
117.8, 131.5, 136.0, 138.7
Mass spectrum m/e: 423 (M+-CH3) Elemental analysis (as C12H16Si2S2Br2)
Actual value C: 32.70, H: 3.66
Calculated value C: 32.73, H: 3.66

Example 6 {Polymerization of 1,1-bis[2-(5-bromothienyl)]tetramethyldisilane} Branch length 15 cm, inner diameter 10
The bottom of a mm Pyrex tube was sealed, a micro rotor and 24.3 mg (1.0 mmol) of magnesium were put therein, and the tube was heated and dried under vacuum. Then tetrahydrofuran 2
ml and 440 mg (1.0 mmol) of 1,1-bis[2-(5-bromothienyl)]tetramethyldisilane were added and heated to 50°C to prepare a Grignard reagent. After cooling, 6.9 mg (0.013 m
mol, 1.3 mol%), degassed and sealed the tube, and
It was heated at ℃ for 100 hours.

After completion of the reaction, hydrolysis was carried out, extraction with chloroform, insoluble components were filtered, reprecipitation was carried out with chloroform/ethanol, and 216 mg (0.77 m
mol units) of poly[(methyltrimethylsilylsilylene)-2,2'-bithienylene] with a yield of 77.
Obtained in %. The melting point of this polymer is 102-107℃/0
．． The weight average molecular weight (Mw) obtained by GPC was 11,000. The results of the instrumental analysis are shown below.

1H nuclear magnetic resonance spectrum (measured in CDCl3 solvent, δppm) 0.20 (s, 9H, Si
(CH3)3), 0.67(s,3H,S
iCH3), 7.17(d,2H,rin
g protons J=3.0Hz),
7.26 (d, 2H, ring protons
J=3.0Hz) 13C nuclear magnetic resonance spectrum (measured in CDCl3 solvent, δppm) -
2.9, -2.2, 125.4, 135.7, 136.
3,143.2

Example 7 Poly[(dimethylsilylene)]-2 obtained in Example 2
, 2'-bithienylene (R and R2 in the above general formula [3] are methyl groups, R3, R4, R5 and R6 are hydrogen atoms, m is 1) was dissolved in 0.1 ml of dichloromethane solvent. Using this solution, a film with a thickness of 1300 Å was formed on an insulating substrate by spin coating. After doping this film by supplying SbF5 in a gas phase, the conductivity of the film was measured. Conductivity was evaluated by applying a voltage to the membrane and measuring the flowing current and voltage using the four-probe method. As a result, the conductivity of this film was 1.2S
/cm.

Example 8 Poly[(methylphenylsilylene] obtained in Example 4)
-2,2'-bithienylene (R in the above general formula [3] is a methyl group, R2 is a phenyl group, R3, R4, R5 and R6 are hydrogen atoms, m is 1) in 0.1 ml of dichloromethane solvent. Dissolved. Using this solution, a film with a thickness of 1620 Å was formed on an insulating substrate by spin coating. After doping this film by supplying SbF5 in a vapor phase, the conductivity of the film was measured in the same manner as in Example 7. As a result, the conductivity of this film was 0.038 S/cm.

Example 9 Poly[(methyltrimethylsilylsilylene)]-2,2'-bithienylene obtained in Example 6 (the general formula [3
] R is trimethylsilyl group, R2 is methyl group, R3
, R4, R5 and R6 are hydrogen atoms, and m is 1) 1 mg was dissolved in 0.1 ml of dichloromethane solvent. Using this solution, a layer of 2000 Å was coated on an insulating substrate by spin coating.
A film with a thickness of . After doping this film by supplying SbF6 in the vapor phase, the conductivity of the film was measured in the same manner as in Example 7. As a result, the conductivity of this film was 0.001.
It was 3S/cm.

Example 10 {Synthesis of 1,2-bis(5-bromothienyl)tetramethyldisilane} In 30 ml of diethyl ether under ice cooling, 2
, 5-dibromothiophene (5.0 ml) and 1.07 g (0.044 mol) of magnesium were added with 4.15 g (0.022 g of 1,2-dichlorotetramethyldisilane) at room temperature. mole)
was added dropwise, and the mixture was stirred under reflux for 3 hours.

After cooling, the oil layer was separated by hydrolysis, washed with water, the aqueous layer was extracted with hexane, the oil layers were combined, dried over anhydrous magnesium sulfate, the solvent was distilled off, and the mixture was distilled under reduced pressure. 3.5 g (0.0795 mol, yield 36%) of 1,2-bis(5-bromothienyl)tetramethyldisilane was obtained. The boiling point of this compound is 125° C./0.1 mmHg, and the results of instrumental analysis are shown below.

1H nuclear magnetic resonance spectrum (measured in CCl4 solvent, δppm) 0.39 (s, 12H, CH
3Si), 6.82(d,2H,ring
protons, J=12Hz), 6
．． 89 (d, 2H, ring protons, J=
12Hz) 13C nuclear magnetic resonance spectrum (CD
Measured in Cl3 solvent, δppm) -2.9
6,117.0,131.4,135.0,140.6
Mass spectrum m/e: 438 (M+) Elemental analysis (as C12H16Br2S2Si2)
Actual value C: 32.70, H: 3.
66 Calculated value C: 32.73, H:
3.66

Example 11 [Polymerization of 1,2-bis(5-bromothienyl)tetramethyldisilane] In 10 ml of tetrahydrofuran at room temperature,
3.5 g (0.0795 mol) of 1,2-bis(5-bromothienyl)tetramethyldisilane and 0.0 g of magnesium.
12.3 mg (bipyridine complex) of NiCl2 (bipyridine complex) was added to the Grignard reagent synthesized from 193 g (0.0795 mol).
0.0000436 mol) and stirred at room temperature for 15 hours. After distilling off tetrahydrofuran, reprecipitation was performed using chloroform/ethanol to obtain 0.25 g (yield: 11%) of poly[(tetramethyldisilanylene)dithienylene]. The melting point of this polymer was 300° C. or higher, and the weight average molecular weight (Mw) obtained by GPC was 9,050. The results of the instrumental analysis are shown below.

1H nuclear magnetic resonance spectrum (measured in CCl4 solvent, δppm) 0.42 (br s, 12
H, CH3Si), 7.25(br s
, 4H, ring protons) 13C nuclear magnetic resonance spectrum (measured in CDCl3 solvent, δp
pm) -2.82, 125.2, 135.
4,137.4,142.7

Example 12 Poly[(tetramethyldisilanylene) obtained in Example 11
dithienylene] (R and R2 in the above general formula [3] are methyl groups, R3, R4, R5 and R6 are hydrogen atoms, m
2) 1 mg was dissolved in 0.1 ml of a 1:1 mixed solvent of dichloroethane and toluene. Using this solution, a film with a thickness of 2100 Å was formed on an insulating substrate by spin coating. After doping this film by supplying SbF5 in a vapor phase, the conductivity of the film was measured in the same manner as in Example 7. As a result, the conductivity σ of this film was 1.89 S/cm.

Example 13 {Synthesis of 1,3-bis[2-(5-bromothienyl)]hexamethyltrisilane} 20 ml of ether and 2,5-dibromothiophene 11.
1 g (45.5 mmol) was added. This was cooled to -80°C, and the tert-butyllithium-hexane solution (
27.0 ml (45.9 mmol) of 1.7 M) was added dropwise over 1 hour, and the temperature was slowly returned to room temperature. 1 more
After stirring at room temperature for 2 hours, 5.6 g (22.9 mmol) of 1,3-dichlorohexamethyltrisilane was added dropwise.
It was refluxed for 3 hours.

After hydrolysis, the oil layer was separated, washed with water, and the aqueous layer was extracted with hexane. The oil layers were combined and dried over anhydrous magnesium sulfate, and then the solvent was distilled off. After that, vacuum distillation (140℃/0.1mmHg) was performed, and further purification was performed using an open column (silica gel, hexane).
2.6 g (5.2 mmol, yield 23%) of bis[2-(5-bromothienyl)]hexamethyltrisilane was obtained. The boiling point of this compound is 140° C./0.1 mmHg, and the results of instrumental analysis are shown below.

1H nuclear magnetic resonance spectrum (measured in CDCl3 solvent, δppm) 0.17 (s, 6H, Si
Si(CH3)2Si), 0.35(s,
12H, (CH3)2SiSi(CH3)2),
6.87 (d, 2H, ring proton
s, J=4Hz), 7.09(d, 2H,
ring protons, J=4Hz) 13C
Nuclear magnetic resonance spectrum (measured in CDCl3 solvent, δp
pm) -2.1, -1.4, 116.6,
131.3, 134.5, 141.8 Mass spectrum m/e: 496 (M+) Elemental analysis (as C14H22Si3S2Br2)
Actual value C: 33.69, H: 4.
41 Calculated value C: 33.73, H:
4.45

Example 14 {Polymerization of 1,3-bis[2-(5-bromothienyl)]hexamethyltrisilane} Branch length 15 cm, inner diameter 1
The bottom of a 0 mm Pyrex tube was sealed, a micro rotator and 24.3 mg (1.0 mmol) of magnesium were placed therein, and the tube was heated and dried under vacuum. Then add 2 ml of tetrahydrofuran and 1,3-bis[2-(5-bromothienyl)]
Hexamethyltrisilane 498mg (1.0mmol)
was added and heated to 50°C to prepare a Grignard reagent. After cooling, 6.9 mg (0.01
3 mmol, 1.3 mol%), degassed and sealed the tube,
It was heated at 30°C for 100 hours.

After completion of the reaction, hydrolysis was performed, extraction with chloroform, insoluble components were filtered, and reprecipitation was performed with chloroform/ethanol to obtain 55 mg (0.16 mmol).
lunits) poly[(hexamethyltrisilanylene)-2,2'-bithienylene] was obtained in a yield of 16%. The melting point of this polymer was 74 to 78°C, and the weight average molecular weight (Mw) obtained by GPC was 10,500. The results of the instrumental analysis are shown below.

1H nuclear magnetic resonance spectrum (measured in CDCl3 solvent, δppm) 0.16 (s, 6H, Si
Si(CH3)2Si), 0.35(s,
12H, Si(CH3)2SiSi(CH3)2),
6.99(d,2H,ring prot
ons, J=3.3Hz), 7.19(d
, 2H, ring protons, J=3.3Hz
) 13C nuclear magnetic resonance spectrum (measured in CDCl3 solvent, δppm) -6.7, -2.0,
125.1 (2C), 134.9, 142.6 Elemental analysis (as C14H22Si3S2) Actual value C: 48.49, H: 6.58
Calculated value C: 49.65, H: 6.55

00
87] Example 15 Poly[(hexamethyltrisilanylene)]-2,2'-bithienylene obtained in Example 14 (the general formula [3]
R and R2 are methyl groups, R3, R4, R5 and R6 are hydrogen atoms, and m is 3) 1 mg was dissolved in 0.1 ml of dichloromethane solvent. Using this solution, a film with a thickness of 2000 Å was formed on an insulating substrate by spin coating. After doping this film by supplying SbF5 in a vapor phase, the conductivity of the film was measured in the same manner as in Example 7. As a result, the conductivity of this film was 1.31 S/cm.

Claims (7)

[Claims] Claim 1: General formula [1] [Formula 1] (wherein R and R2 each independently represent a group selected from the group consisting of an alkyl group, an aryl group, an aralkyl group, an alkylsilyl group, and an arylsilyl group) ,R3,
R4, R5 and R6 each independently represent a hydrogen atom or a group selected from the group consisting of an alkyl group, an aryl group, an aralkyl group and an alkoxy group, and X and X2
each independently represents a halogen atom, and m represents a number of 1 or more. ) A bis(5-halogen-substituted thienyl)silane derivative. [Claim 2] General formula [2] [Formula 2] (wherein R and R2 each independently represent a group selected from the group consisting of an alkyl group, an aryl group, an aralkyl group, an alkylsilyl group, and an arylsilyl group) ,R3,
R4, R5 and R6 each independently represent a hydrogen atom or a group selected from the group consisting of an alkyl group, an aryl group, an aralkyl group and an alkoxy group, and X and X2
each independently represents a halogen atom, and m represents a number of 1 or more. ) Bis(5-halogenmagnesiumthienyl)silane derivative. [Claim 3] General formula [3] [Formula 3] (wherein R and R2 each independently represent a group selected from the group consisting of an alkyl group, an aryl group, an aralkyl group, an alkylsilyl group, and an arylsilyl group) ,R3,
R4, R5 and R6 each independently represent a hydrogen atom or a group selected from the group consisting of an alkyl group, an aryl group, an aralkyl group and an alkoxy group, m represents a number of 1 or more, and n represents a number of 2 or more. show. ) A polysilane compound represented by [Claim 4] General formula [4] [Formula 4] (wherein R7 and R8 each independently represent a hydrogen atom or a group selected from the group consisting of an alkyl group, an aryl group, an aralkyl group, and an alkoxy group, 2-halogen-substituted-5- obtained by reacting a 2,5-dihalogen-substituted thiophene derivative represented by (X3 and X4 each independently represent a halogen atom) with magnesium.
2-2, which is obtained by reacting a halogen magnesium thiophene derivative or a 2,5-dihalogen-substituted thiophene derivative represented by the general formula [4] with a lithiation reagent.
The halogen-substituted 5-lithium thiophene derivative has the general formula [5] [Chemical formula 5] (wherein R and R2 are each independently selected from the group consisting of an alkyl group, an aryl group, an aralkyl group, an alkylsilyl group, and an arylsilyl group). represents a selected group, X5 and X6 each independently represent a halogen atom, m is 1
Indicates the above number. General formula [1] [Chemical formula 6] characterized by reacting dihalogen-substituted silanes represented by Represents a group selected from the group consisting of silyl groups, R3,
R4, R5 and R6 each independently represent a hydrogen atom or a group selected from the group consisting of an alkyl group, an aryl group, an aralkyl group and an alkoxy group, and X and X2
each independently represents a halogen atom, and m represents a number of 1 or more. ) A method for producing a bis(5-halogen-substituted thienyl)silane derivative. [Claim 5] General formula [1] [Formula 7] (wherein R and R2 each independently represent a group selected from the group consisting of an alkyl group, an aryl group, an aralkyl group, an alkylsilyl group, and an arylsilyl group) ,R3,
R4, R5 and R6 each independently represent a hydrogen atom or a group selected from the group consisting of an alkyl group, an aryl group, an aralkyl group and an alkoxy group, and X and X2
each independently represents a halogen atom, and m represents a number of 1 or more. General formula [2] characterized by reacting a bis(5-halogen-substituted thienyl)silane derivative represented by , represents a group selected from the group consisting of an aralkyl group, an alkylsilyl group and an arylsilyl group, R3,
R4, R5 and R6 each independently represent a hydrogen atom or a group selected from the group consisting of an alkyl group, an aryl group, an aralkyl group and an alkoxy group, and X and X2
each independently represents a halogen atom, and m represents a number of 1 or more. ) A method for producing a bis(5-halogenmagnesiumthienyl)silane derivative. [Claim 6] General formula [1] [Chemical formula 9] (wherein R and R2 each independently represent a group selected from the group consisting of an alkyl group, an aryl group, an aralkyl group, an alkylsilyl group, and an arylsilyl group) ,R3,
R4, R5 and R6 each independently represent a hydrogen atom or a group selected from the group consisting of an alkyl group, an aryl group, an aralkyl group and an alkoxy group, and X and X2
each independently represents a halogen atom, and m represents a number of 1 or more. ) A bis(5-halogen magnesium thienyl) silane derivative obtained by reacting a bis(5-halogen-substituted thienyl) silane derivative represented by ) with magnesium is polymerized in the presence of a transition metal complex catalyst. General formula [3] [Formula 10] (wherein R and R2 each independently represent a group selected from the group consisting of an alkyl group, an aryl group, an aralkyl group, an alkylsilyl group, and an arylsilyl group, R3,
R4, R5 and R6 each independently represent a hydrogen atom or a group selected from the group consisting of an alkyl group, an aryl group, an aralkyl group and an alkoxy group, m represents a number of 1 or more, and n represents a number of 2 or more. show. ) A method for producing a polysilane compound represented by 7. The main chain has the general formula [3] [Chemical formula 11] (wherein R and R2 are each independently selected from the group consisting of an alkyl group, an aryl group, an aralkyl group, an alkylsilyl group, and an arylsilyl group) R3,
R4, R5 and R6 each independently represent a hydrogen atom or a group selected from the group consisting of an alkyl group, an aryl group, an aralkyl group and an alkoxy group, m represents a number of 1 or more, and n represents a number of 2 or more. show. ) A conductive material comprising a polysilane compound having repeating units of silanylene dithienylene units.