JPH03146522A - Polysilane compound, preparation method and its use - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a new and useful polysilane compound, a method for producing the same, and a conductive material.

[Conventional technology]

Conventionally, metals have been used exclusively as materials requiring 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.

For example, in 1981, methylphenylpolysilane, a type of polysilane, was irradiated with light to obtain a compound with a crosslinked structure, and a dopant (doping agent) was added to this compound.
It has been found that a compound with high electrical conductivity can be obtained by adding . A compound such as AsF is used as the dopant, and it is disclosed that by using such a dopant, the silicon-containing compound exhibits a conductivity of about 0.53/cm (J , A+mar, Che+++, Sa
c., 103.7352-7354 (1981)).

However, in order to use the above-mentioned silicon-containing compounds as conductive materials, it is necessary to use highly toxic AsF as a dopant.
In addition, when producing silicon-containing compounds such as those mentioned above, there are problems in that it is difficult to control light irradiation and it is difficult to produce compounds with good properties with good reproducibility. Japanese Patent No. 62-59632 discloses a matrix-like polyalkylsilane that exhibits excellent conductivity without using AsF. It has been shown here that by incorporating sulfate ions as a dopant into polyalkylsilane, polyalkylsilane has an electrical conductivity of about 10-'=1O3/cm.

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

[Problem to be solved by the invention]

It is an object of the present invention to provide new and useful polysilane compounds.

Another object of the present invention is to propose a manufacturing method for easily and efficiently manufacturing the above polysilane compound.

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.

[Means to solve the problem]

The present invention relates to the following general formula [I] (wherein RL and R2 are each independently an alkyl group,
Represents a group selected from the group consisting of an aryl group and an aralkyl group, R3 and R4 each independently represent a hydrogen atom,
Alternatively, it represents a group selected from the group consisting of an alkyl group, an aryl group, an aralkyl group, and an alkoxy group, and n represents an integer of 2 or more. ), a method for producing the same, and a conductive material made of the polysilane compound.

The above general formula [! ] R1 and R2 are groups selected from the group consisting of an alkyl group, an aryl group, and an aralkyl group, and R1 and R2 may be the same or different.

Examples of the alkyl group represented by R'' and R2 include those having 1 to 6 carbon atoms, preferably 1 to 3 carbon atoms.The alkyl group may be linear or branched. Specific examples of the alkyl group include linear alkyl groups such as methyl group, ethyl group, n-propyl group, and n-butyl group; secondary alkyl groups such as isopropyl group, 5ee-butyl group, and 5ee-amyl group. group; tart-
Examples include tertiary alkyl groups such as butyl group and tart-amyl group.

The aryl group represented by R1 and R2 includes a monovalent aryl group having at least one aromatic ring. This aromatic ring may have a substituent. Specific examples of such an aryl group include a phenyl group, a naphthyl group, a tolyl group, and a xylyl group.

Furthermore, as the aralkyl group represented by R1 and R2,
Examples 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,
Examples include tolylmethyl group.

When the polysilane compound of the present invention is used as a conductive material, R1 and R2 are methyl groups and ethyl groups.

A combination of groups selected from the group consisting of a phenyl group and a benzyl group is preferred, and a combination of methyl groups and a combination of a methyl group and a phenyl group are particularly preferred.

R' and R4 in the above-mentioned -Moreka (1) are 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 R3 and R4 may be the same or different.

Examples of the alkyl group represented by R3 and R4 include those having 1 to 8 carbon atoms, preferably 1 to 6 carbon atoms. Alkyl groups may be linear or branched.8 Specific examples of such alkyl groups include linear alkyl groups such as methyl, ethyl, n-propyl, and n-butyl groups. ; Secondary alkyl group such as isopropyl group, 5ec-butyl group, 5ee-amyl group; tart
Examples include tertiary alkyl groups such as -butyl group and tart-amyl group.

The aryl group represented by R3 and R4 includes a monovalent aryl group having at least I aromatic ring. This aromatic ring may have a substituent. Specific examples of such an aryl group include a phenyl group, a naphthyl group, a tolyl group, and a xylyl group.

Further, as the aralkyl group represented by Rj and R4,
Examples 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:

Examples include benzyl group, phenethyl group, α-methylbenzyl group, and tolylmethyl group.

The alkoxy group represented by R3 and R4 has 1 to 8 carbon atoms. Preferably, 1 to 6 can be mentioned. The alkoxy group may be linear or branched; examples of such alkoxy groups include linear alkoxy groups such as methoxy, ethoxy, n-propoxy, and n-butoxy; isopropoxy; Base, 5ee
Secondary alkoxy groups such as -butoxy group and 5ec-amyloxy group; tertiary alkyl groups such as tert-butoxy group and tart-amyloxy group; and the like.

When the polysilane compound of the present invention is used as a conductive material, a combination in which R3 and R4 are selected from the group consisting of hydrogen, methyl group, ethyl group, phenyl group, benzyl group and methoxy group is preferred.

In the above-mentioned - pattern hole (1), n is an integer of 2 or more. When using the polysilane compound of the present invention as a conductive material, n
is preferably 10 or more and an average molecular weight of 2,000 to 3,000 or more.

The polysilane compound of the present invention has the following formula (II) (wherein R1 and R2 each independently represent a group selected from the group consisting of an alkyl group, an aryl group, and an aralkyl group, and R3 and R4 each independently Produced by reacting a 2,5-bis(chlorosilyl)thiophene derivative represented by 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 with an alkali metal. can do.

Specific examples of the 2,5-bis(chlorosilyl)thiophene derivative represented by the above-mentioned symbol (n) include 2,5-bis(chlorodimethylsilyl)thiophene,
2,5-bis(chloromethylethylsilyl)thiophene, 2,5-bis(chloromethylphenylsilyl)thiophene, 2,5-bis(chloromethyltolylsilyl)thiophene, 2,5-bis(chloromethylphenylsilyl)
-3-methylthiophene and the like can be mentioned.

When the polysilane compound of the present invention is used as a conductive material, 2,5-bis(chlorodimethylsilyl)thiophene or 2,5-bis(chloromethylphenyl) Preferably, silyl)thiophene is used.

Although 2,5-bis(chlorosilyl)thiophene derivatives are usually used alone, they can also be used in combination with 2Wi or more derivatives, for example, for the purpose of adjusting the conductivity of the resulting polysilane compound.

The 2,5-bis(chlorosilyl)thiophene derivative represented by the above-mentioned -Momonena (III) has, for example, a predetermined substituent (R
2,5-chenylene dimagnesium bromide synthesized from 2,5-dibromothiophene having 3,R') and magnesium is reacted with monochloro-substituted hydrosilanes having predetermined substituents (R'', R2).

After preparing 2.5-bis(substituted hydrosilyl)thiophenes, this was treated with palladium chloride (PdCQ2) in carbon tetrachloride.
), it can be produced by stirring at room temperature or under heating.

Examples of the alkali metal include metal sodium rum,
Examples include metallic lithium and metallic potassium. Among these, it is preferable to use sodium metal. These alkali metals can be used alone or in combination of two or more.

An example of the reaction between a 2.5-bis(chlorosilyl)thiophene derivative and an alkali metal is shown below.

(In the formula, R1 to R' and n are the same as above.) As shown in the above formula (Ill), in the reaction of the 2,5-bis(chlorosilyl)thiophene derivative and the alkali metal, the alkali metal is at least It is desirably used in an amount such that it reacts with the chlorine atom in the 2,5-bis(chlorosilyl)thiophene derivative.1 Usually 1.2 to 5 mol, preferably 1.2 to 5 mol per mol of the 2,5-bis(chlorosilyl)thiophene derivative. is preferably used in a range of 2 to 4 moles.

According to the reaction mechanism of the above formula [I[1], the -Momona (
The repeating unit represented by 1) can be expressed as shown below (mV), but when viewed as a polymer, they are substantially the same.

(In the formula, R1-R4 and n are the same as above.) The alkali metal is usually dispersed in a solvent inert to the alkali metal and used in the form of a dispersion. desirable.

Therefore, the reaction between the 2,5-bis(chlorosilyl)thiophene derivative and the alkali metal is generally carried out as a liquid phase reaction using a solvent. As mentioned above, as a solvent,
It is desirable to use a solvent that has no reactivity to alkali metals, is inert, and is also inert to the 2,5-bis(chlorosilyl)thiophene derivative as a raw material. Specific examples of such solvents include aromatic hydrocarbon solvents such as benzene, toluene, and xylene; saturated hydrocarbon solvents such as n-decane; unsaturated hydrocarbon solvents; and ether solvents. I can give it to you.

In particular, aromatic hydrocarbon solvents such as toluene, benzene, and xylene or saturated hydrocarbon solvents such as n-decane are preferably used. These solvents can be used alone or in combination of two or more.

The reaction is preferably carried out at a reaction temperature of usually -20°C to 180°C, preferably 0 to 150°C, and the polymerization reaction can be carried out under reduced pressure or increased pressure, and the reaction pressure is not limited. However, usually under reduced pressure or 60kg/cd-
G, preferably in the range of 0 to 30 kg/aJ-G, particularly preferably in the range of 0 to 5 kg/cd-G. The reaction time is appropriately set in consideration of reaction temperature, reaction pressure, etc. 1 Usually 5 minutes. ~100 hours, preferably 1 to 10 hours.

The reaction can also be carried out while irradiating ultrathermal waves.

In this case, the reaction temperature is usually -20 to 100°C, preferably 0 to 50°C, the reaction time is usually 5 minutes to 50 hours, preferably 1 to 20 hours, and the reaction pressure is usually 0 to 30 kg/d-
6, preferably 0 to 5 kg/dG.

Further, the 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 produced in this way.

The repeating unit is represented by the formula (1) above, and the terminal group is the raw material used and the formula (nl)
It has something derived from the reaction of

After the reaction is completed, a polysilane compound can be obtained by hydrolyzing the alkali metal, followed by extraction with a solvent such as chloroform or benzene, followed by reprecipitation by adding an alcohol such as ethanol or impropatol.

In this way, the above-mentioned formula (
The polysilane compound represented by I) usually has a conductivity σ of 10−”S/c+o or less, but by adding a dopant, the conductivity σ usually increases from 0.01 to 10S/C1
It will be about 1. 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.

By adding a dopant, the polysilane compound of the present invention exhibits better conductivity. 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 1, for example, SO, AsF, SbF,
.

5bCQ5, etc. Among these, SbF is preferable.These dopants alone,
Moreover, two or more types can be used in combination.

The method of adding a dopant to a polysilane compound is not particularly limited. For example, a method of molding a polysilane compound into an arbitrary shape, such as a film shape, and then applying a dopant to this molded product, or a method of adding a dopant to a polysilane compound and then adding a dopant to Various methods can be employed, such as a method of forming into a shape.

The molding method and the shape of the molded body at this time are not particularly limited, and depend on the shape of the intended conductive material.

It can be formed into any shape such as a film or a line 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, for example, by utilizing the optical functionality of the silicon-silicon bond.

〔Effect of the invention〕

According to the present invention, a novel and useful polysilane compound having a repeating unit represented by the above formula (1) can be obtained. Such a polysilane compound can be easily and efficiently produced by reacting the 2,5-bis(chlorosilyl)thiophene derivative represented by the formula [■] with an alkali metal.

Further, according to the present invention, a conductive material exhibiting excellent conductivity can be easily obtained with good reproducibility.

〔Example〕

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 (1) Synthesis of 2.5-bis(chlorodimethylsilyl)thiophene Tetrahydrofuran (THF) and benzene 1:1
In 40mfl of mixed solvent, 4.2mM (0,0281mol) of 2,5-dibromothiophene and 1.6mM of magnesium
Tog of dimethylchlorosilane (0,106 mol) was added to 2,5-chenylene dimagnesium bromide synthesized from g (0,0694 mol) and stirred at room temperature for 10 hours, followed by hydrolysis. Furthermore, the oil layer was separated, dried, and then distilled under reduced pressure to obtain 4.0 g (yield: 71%) of 2.5-bis(dimethylsilyl)thiophene. The boiling point of this compound is 100° C./16 mmHg, and the results of instrumental analysis are shown below.

1H nuclear magnetic resonance spectrum (measured in CC124 solvent.

δppm) 0.39 (d, 12H, J=4Hz, CH35i)
;5.55(sept, 2H, J=4Hz, H5
i) ;8.31(s, 2H, ring proto
ns) Infrared absorption spectrum v 5i-41; 2130 cm-1 Mass spectrum tile 200 (M”) Elemental analysis (as C, H engineering, SSi) Actual value C,
47,64: H, 8,00 calculated value C, 47,94;
H,8,05 The 2,5-bis(dimethylsilyl)thiophene obtained above was stirred at room temperature for 20 hours in carbon tetrachloride in the presence of a catalytic amount of palladium chloride.0 Then, after distilling off the carbon tetrachloride , the residual liquid was distilled under reduced pressure to obtain 2,5-bis(
chlorodimethylsilyl)thiophene 4.7g (yield 66
%) was obtained. The boiling point of this compound is 125℃/15mmH
g, and the results of the instrumental analysis are shown below.

1H nuclear magnetic resonance spectrum (measured in CCQ4 solvent, δ
ppm) 0.70 (s, 12H, CH, SL); 7.23
(s, 241. ring protons) 13C
Nuclear magnetic resonance spectrum (measured in CDCjli solvent, δ
pp-) 3.3.136.7.143.5 Mass spectrum tale 26g (M”) Elemental analysis (as C, H14CQ, SSi) Actual value
C, 35, 45; H, 5, 20 calculated value C, 35, 6
8: Polymerization of H,5,24(n)2,5-bis(chlorodimethylsilyl)thiophene. 1.1 g of sodium (0,04
78 mol) was added, stirred to disperse, and 4.7 g of 2,
5-bis(chlorodimethylsilyl)thiophene (0,0
175 mol) was added. After stirring at 130°C for 10 hours, the mixture was hydrolyzed, extracted with chloroform, dried, the solvent was distilled off, and reprecipitated in benzene/ethanol.
2 g of polymer was obtained. As a result of measuring the molecular weight using GPC, the weight average molecular weight (Mw) was 17000,
The melting point was 155-161° C. The results of zero-instrument analysis are shown below.

1H nuclear magnetic resonance spectrum (cocn, measured in solvent,
δppm) 0.34 (s, 1211. CH, SL); 7.1
4(s, 2H, ring protons) C nuclear magnetic resonance spectrum (CDfjl, measured in solvent, δp
pm) -2,5,135,6,143,9 Practical Example 2 (1) Synthesis of 2,5-bis(chloromethylphenylsilyl)thiophene 2,5-dibromothiophene 4.2-(0 ,0281 mole> and red sea bream, sium 1,6
15 g (0,0958 mol) of chloromethylphenylsilane was added to 2,5-chenylene dimagnesium bromide synthesized from g (0,0694 mol), and the mixture was heated and stirred at 50° C. for 3 hours. After hydrolysis and extraction with hexane, it was dried over anhydrous magnesium sulfate, the solvent was distilled off, and 7.9 g of 2,5-bis(methylphenylsilyl)thiophene was obtained by distillation under reduced pressure (yield: 84%). ), the boiling point of this compound is 125-128°C 10.2 mmHg,
The results of the instrumental analysis are shown below.

1H nuclear magnetic resonance spectrum (measured in CCQ4 solvent, δ
ppm) 0.64 (d, 6) 1. J=4Hz, (Jl, S
i) ;5.01(sept, 2H, J=4Hz,
HSi); 7.04-7.64 (m, 12Hyr
ing protons) Infrared absorption spectrum vSi-) 1: 2130cm-1 Mass spectrum + a/e 324 (M”) Elemental analysis CCt*Hx.SSi) Actual measurement value C,
66,57; H, 6,18 calculated value C, 66,21;
H,6,21 The 2,5-bis(methylphenylsilyl)thiophene obtained above was treated in the same manner as in Example 1 to obtain 7.2 g of 2,5-bis(chloromethylphenylsilyl)thiophene. (yield 75%), the boiling point of this compound was 190°C/Q, 8 mmHg, and the results of one-instrument analysis are shown below.

1!1 nuclear magnetic resonance spectrum (measured in CCQ4 solvent.

δppm) 0.94 (s, 6Hy CH35l) Near, 20-
7.87 (m, 12H, ring proton
s) "3C nuclear magnetic resonance spectrum (measured in CDCQ3 solvent.

δppm) 2.1.128.2.130, 9.133.8.137
．． 1.138.0゜142.5 Elemental analysis (as Cza) lx * cflzssiz) Actual value C, 66,57; H, 6, 18 Calculated value C, 66
,61: H,6,21(II) Polymerization of 2,5-bis(chloromethylphenylsilyl)thiophene 0.6 g of sodium (0,02
60 mol), stir to disperse, and then
Bis(chloromethylphenylsilyl)thiophene 3.0
g (0,00763 mol) was added. The mixture was stirred at room temperature for 10 hours while being irradiated with ultrasonic waves. After hydrolysis, reprecipitation was performed once each with chloroform/ethanol and chloroform/isopropanol to obtain 1.79 g of polymer. The melting point of this polymer was 68 to 74°C, and the weight average molecular weight (My) obtained by GPC was 58,000.The results of zero-instrument analysis are shown below.

1H nuclear magnetic resonance spectrum (CDCjl, measured in solvent, δppm) 0.65 (s, 6H+ CH, SL) near, 12-
7.34 (a, 12H, ring protons)
13C nuclear magnetic resonance spectrum (CDCQ, measured in solvent.

δpp+m) -3,3,127,8,129,1,L34.7.13
5.8.137.5゜142.0 Elemental analysis CC1*H1aSSi@) Actual measurement value C,
67,28; H, 5,68 calculated value C, 67,02;
H,5,62 Example 3 (1) 2,5-bis(chloromethyltolylsilyl>
Synthesis of thiophene T) 2,5-dibromothiophene in IF 50-4.
20 (0,0281 mol) and magnesium 1.6 g (0
, 0694 mol) and chloromethyltolylsilane 15
g (0,0880 mol) and stirred at 50° C. for 3 hours. After hydrolysis, it was extracted with hexane and dried over anhydrous magnesium sulfate. The solvent was distilled off and 2,
7.4 g of 5-bis(methyltolylsilyl)thiophene was obtained (yield 75%). The boiling point of this compound is 185℃10
．． 9mm)! g, and the results of one-instrument analysis are shown below.

1H nuclear magnetic resonance spectrum (measured in CCQ4 solvent, δ
pp seal) 0.63 (d, 6) 1. J=4Hz, C)+3sl)
;2.30(s, 6H,P-Me) ;4.96(q
, 2)1. J=4Hz, HSi) ;7.05(
d, 48. J=20Hz, tolyL ring
protons); 7.19 (d, 4H, J=70
Hz, tolyl ring protons);
7.19(s, 2)1. thiophene ri
ng protons) Infrared absorption spectrum v 5i-II; 2130 cm-'Mass spectrum tale 352 (M'') Elemental analysis (as CZ.H,,5Si2) Actual value C,
68,02: H,6,79 calculated value C,68,12:
H,6,86 The 2,5-bis(methyltolylsilyl)thiophene obtained above was treated in the same manner as in Example 1 to give 2,
5-bis(chloromethyltolylsilyl)thiophene6.
4 g (yield 72%) was obtained. The boiling point of this compound is 1
The temperature was 90°C and 10.3+omHg, and the results of instrumental analysis are shown below.

1H nuclear magnetic resonance spectrum (measured in CCQ4 solvent, δ
ppm) 0.93 (s, 6H, CH35i); 2.35 (s
, 6H,P-Me) ;7.17(d, 4H,J=
18) 1z, tolyl ring protons
) ;7.26(d, 4H, J=18Hz, tol
yl ring protons) ;7.30(s,
2H, thiophene ring proton
s) 13C nuclear magnetic resonance spectrum (measured in CDCQ3 solvent, δppm) 2.2.21.6.129.0.130.5.133.
9.137.8°141.1.142.7 Mass spectrum m/e 420 (M”) Elemental analysis (as C2oH22C2,5Si2) Actual value C,56,92; H,5,17 Calculated value C,57,
00; H,5,26(II) 0.5 g of sodium (0,02
17 mol) was added, stirred to disperse, and 3.2 g of 2,
5-bis(chloromethyltolylsilyl)thiophene (0
,00759 mol) of benzene 4+mQ solution was added.

The mixture was stirred at room temperature and irradiated with ultrasonic waves for 10 hours. After hydrolysis and extraction with chloroform, it was dried over anhydrous magnesium sulfate, the solvent was distilled off, and the remaining liquid was reprecipitated twice with chloroform/ethanol to obtain 1.2 g of polymer (yield: 46%).
). The melting point of this polymer was 86-92°C, and the weight average molecular weight (axis) measured by GPC was 62,000.

The results of the instrumental analysis are shown below.

1H nuclear magnetic resonance spectrum (measured in CDCQ3 solvent,
δpp ugly) 0.69 (s, 6H, C) I, Si); 2.29 (
s, 6H, P-Me); 6.72-7.55(m
, IOH, ring protons) 13G nuclear magnetic resonance spectrum (CDCI2. Measured in solvent, δpp
+m) -3,1,21,5,128,7,132,3,132
,4,134,9゜137.4.138.9.142.
1 Example 4 Polymer obtained in Example 1 (polydisilanylentidine, R1 and R2 in the general formula (1) are methyl groups)
1 mg to 1:1 of 0.1-dichloroethane and toluene
was dissolved in a mixed solvent of Using this solution, a film with a thickness of 20 OA was formed on an insulating substrate using a spin code solution.

After doping this film by supplying SbF in a gas phase, the conductivity of the film was measured. The conductivity was evaluated by applying a voltage to the membrane and measuring the flowing WL current and voltage using a four-probe method. As a result, the conductivity σ of this film was 5.473/am.

Example 5 1 mg of the polymer obtained in Example 2 (polydisilanilentinidine, in the general formula (1), R1 is a methyl group and R2 is a phenyl group) was dissolved in 0.1 vR of dichloroethane. Using this solution, a film with a thickness of 6100 nm was formed on an M-edge substrate using a spin code solution.

After doping this film by supplying SbF 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 σ
was 2,33 S/cm.

Example 6 The polymer IB obtained in Example 3 (polydisilanilentinidine, in the general formula (I), R1 is a methyl group and R2 is a tolyl group) was dissolved in 0.1 mQ of dichloroethane. This solution was used to coat an insulating substrate with a spin code solution for 27 minutes.
A film with a thickness of 0.000 people was formed.

After doping this film by supplying SbF 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 σ
was 0.01870m.

Claims (3)

[Claims] (1) The following general formula [I] ▲There are mathematical formulas, chemical formulas, tables, etc.▼... [I] (In the formula, R^1 and R^2 are each independently from the group consisting of an alkyl group, an aryl group, and an aralkyl group. R^3 and R^4 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;
n represents an integer of 2 or more. ) A polysilane compound represented by (2) The following general formula [II] ▲ Numerical formulas, chemical formulas, tables, etc. are included ▼... [II] (In the formula, R^1 and R^2 are each independently from the group consisting of an alkyl group, an aryl group, and an aralkyl group. R^3 and R^4 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. The following general formula [I] is characterized by reacting a bis(chlorosilyl)thiophene derivative with an alkali metal. ▲There are mathematical formulas, chemical formulas, tables, etc.▼...[I] (In the formula, R^1 and R ^2 each independently represents a group selected from the group consisting of an alkyl group, an aryl group, and an aralkyl group, and R^3 and R^4 each independently represent a hydrogen atom, or an alkyl group, an aryl group, an aralkyl group, and an alkoxy group. Indicates a group selected from the group consisting of
n represents an integer of 2 or more. ) A method for producing a polysilane compound represented by (3) The following general formula▲ Numerical formula, chemical formula, table, etc.▼ (In the formula, R^1 and R^2 each independently represent a group selected from the group consisting of an alkyl group, an aryl group, and an aralkyl group, and R ^3 and R^4 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,
n represents an integer of 2 or more. ) A conductive material comprising a polysilane compound having disilanylentienylene represented by the following as a repeating unit.