3, 4-ethylenedioxythiophene derivative and conductive composition

Abstract

To provide a new conductive composition having high conductivity and easily soluble in an organic solvent, and to provide a 3, 4-ethylenedioxythiophene derivative for producing the conductive composition.SOLUTION: The 3, 4-ethylenedioxythiophene derivative of the present invention is characterized by having either one of two kinds of substituents having a specific structure and a siloxane bond. The conductive composition of the present invention is characterized by containing a polymer having a structural unit derived from the 3, 4-ethylenedioxythiophene derivative of the present invention in the molecule and a dopant.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a novel conductive composition and a 3,4-ethylenedioxythiophene derivative for producing the conductive composition. [Background technology]

[0002] Polythiophenes, which are composed of repeatedly bonded thiophene rings, are expected to be used as diverse electronic materials due to the breadth of their π-conjugated systems. However, conventional poly(3,4-ethylenedioxythiophene) is insoluble in water and organic solvents, limiting its uses. Furthermore, poly(3-thiophene derivatives), although soluble in organic solvents, have low electrical conductivity, making their practical application problematic.

[0003] Patent Document 1 discloses compounds represented by chemical formulas (IV) and (V) as 3-substituted thiophenes and describes a method for polymerizing them. Although the solubility of the resulting polymer in hydrocarbon organic solvents has been confirmed, there is no mention of electrical conductivity. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Japanese Patent Application Laid-Open No. 2015-30789 Summary of the Invention [Problem to be solved by the invention]

[0005] When using conductive polymers in electronic components, etc., they are required to be soluble in a variety of organic solvents and also to have high conductivity, and even the technology described in Patent Document 1 still has room for improvement.

[0006] In view of the above circumstances, an object of the present invention is to provide a novel conductive composition that has high conductivity and can be easily dissolved in an organic solvent, and a 3,4-ethylenedioxythiophene derivative for producing the conductive composition. [Means for solving the problem]

[0007] As a result of extensive research aimed at solving the above problems, the present inventors have found that introducing a substituent having a siloxane bond into 3,4-ethylenedioxythiophene is effective in increasing solubility in organic solvents.

[0008] That is, the 3,4-ethylenedioxythiophene derivative of the present invention is characterized by being represented by the following general formula (1) or (2).

[0009] [ka]

[0010] In the above general formula (1), R 1 is a linear or branched, substituted or unsubstituted alkylene group having 2 to 6 carbon atoms, and R 2 and R 3 are each a linear or branched alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkynyl group having 2 to 12 carbon atoms, or a cycloalkyl group having 3 to 12 carbon atoms, which may contain a silicon-oxygen bond and has a dialkyl group on the silicon; R 4 , R 5 and R 6 are the same or different groups each consisting of a linear or branched alkoxy group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkynyl group having 2 to 12 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, or hydrogen, and m is R 2 , R 3 is a number from 2 to 6 that represents the number of repeating units of silicon-oxygen bonds that may be the same or different groups.

[0011] [ka]

[0012] In the above general formula (2), R 7 is a linear or branched, substituted or unsubstituted alkylene group having 2 to 6 carbon atoms, and R 8 and R 9 are each a linear or branched alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkynyl group having 2 to 12 carbon atoms, or a cycloalkyl group having 3 to 12 carbon atoms, which may contain a silicon-oxygen bond and has a dialkyl group on the silicon; R 10 , R 11 and R 12 are the same or different groups each consisting of a linear or branched alkoxy group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkynyl group having 2 to 12 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, or hydrogen, and n is R 8 , R 9 is a number from 2 to 6 that represents the number of repeating units of silicon-oxygen bonds that may be the same or different groups.

[0013] The conductive composition of the present invention is characterized by containing a polymer (polymer for conductive composition) having a structural unit (repeating unit) represented by the following general formula (3) or (4) in its molecule, and a dopant.

[0014] [ka]

[0015] In the above general formula (3), R 1 is a linear or branched, substituted or unsubstituted alkylene group having 2 to 6 carbon atoms, and R 2 and R 3are each a linear or branched alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkynyl group having 2 to 12 carbon atoms, or a cycloalkyl group having 3 to 12 carbon atoms, which may contain a silicon-oxygen bond and has a dialkyl group on the silicon; R 4 , R 5 and R 6 are the same or different groups each consisting of a linear or branched alkoxy group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkynyl group having 2 to 12 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, or hydrogen, and m is R 2 , R 3 is a number from 2 to 6 that represents the number of repeating units of silicon-oxygen bonds that may be the same or different groups.

[0016] [ka]

[0017] In the above general formula (4), R 7 is a linear or branched, substituted or unsubstituted alkylene group having 2 to 6 carbon atoms, and R 8 and R 9 are each a linear or branched alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkynyl group having 2 to 12 carbon atoms, or a cycloalkyl group having 3 to 12 carbon atoms, which may contain a silicon-oxygen bond and has a dialkyl group on the silicon; R 10 , R 11 and R 12 are the same or different groups each consisting of a linear or branched alkoxy group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkynyl group having 2 to 12 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, or hydrogen, and n is R 8 , R 9 is a number from 2 to 6 that represents the number of repeating units of silicon-oxygen bonds that may be the same or different groups. [Effects of the Invention]

[0018] According to the present invention, it is possible to provide a novel conductive composition that has high conductivity and can be easily dissolved in an organic solvent, and a 3,4-ethylenedioxythiophene derivative for producing the conductive composition. DETAILED DESCRIPTION OF THE INVENTION

[0019] The 3,4-ethylenedioxythiophene derivative of the present invention is represented by the above general formula (1) or (2).

[0020] The conductive composition of the present invention contains a polymer having a structural unit represented by the above general formula (3) or (4) in the molecule.

[0021] The structural unit represented by the general formula (3) is introduced into the polymer by polymerizing the 3,4-ethylenedioxythiophene derivative represented by the general formula (1) as a monomer. 1 ~R 6 and m are R in the above general formula (1), 1 ~R 6 and m.

[0022] The structural unit represented by the general formula (4) is introduced into the polymer by polymerizing the 3,4-ethylenedioxythiophene derivative represented by the general formula (2) as a monomer. 7 ~R 12 and n are R in the above general formula (2), 7 ~R 12 and n.

[0023] The polymer contained in the conductive composition has a structural unit in which a substituent having a siloxane skeleton is introduced into a 3,4-ethylenedioxythiophene skeleton, as represented by the general formula (3) or (4), and therefore has high solubility in organic solvents, such as halogenated organic solvents such as dichloromethane and chloroform.

[0024] Moreover, the conductive composition containing the above polymer and dopant can ensure higher conductivity than the conductive composition containing the polymer described in Patent Document 1, for example.

[0025] The polymer contained in the conductive composition may have only one of the structural units represented by the general formula (3) and the structural units represented by the general formula (4) in the molecule, or may have both the structural units represented by the general formula (3) and the structural units represented by the general formula (4) in the molecule. When the polymer has both the structural units represented by the general formula (3) and the structural units represented by the general formula (4) in the molecule, there are no particular restrictions on the ratio thereof.

[0026] The polymer contained in the conductive composition may have other structural units in the molecule in addition to the structural unit represented by the general formula (3) and / or the structural unit represented by the general formula (4). Examples of such other structural units include a structural unit derived from thiophene, and a structural unit derived from 3,4-ethylenedioxythiophene or alkylated 3,4-ethylenedioxythiophene represented by the following general formula (5).

[0027] [ka]

[0028] In the above general formula (5), R 13 is hydrogen or an alkyl group having 1 to 10 carbon atoms.

[0029] That is, among the structural units represented by the general formula (5), R 13 is a structural unit derived from 3,4-ethylenedioxythiophene, and R 13 R is an alkyl group having 1 to 10 carbon atoms, which is a structural unit derived from alkylated 3,4-ethylenedioxythiophene. 13 When is an alkyl group having 1 to 10 carbon atoms, those having 1 to 4 carbon atoms, that is, alkyl groups such as methyl, ethyl, propyl and butyl groups are particularly preferred.

[0030] In the polymer contained in the conductive composition, when the total structural units (total repeating units) of the polymer are taken as 100 mol%, the ratio of the structural units represented by the general formula (3) and the structural units represented by the general formula (4) [when only one of the structural units represented by the general formula (3) and the structural units represented by the general formula (4) is contained, this is the ratio, and when both are contained, this is the total ratio of these. The same applies below.] is preferably 5 mol / % or more, more preferably 20 mol / % or more, from the viewpoint of maintaining good solubility in organic solvents. Therefore, when the polymer contains other structural units in addition to the structural units represented by the general formula (3) and / or the structural units represented by the general formula (4), the ratio of the other structural units is desirably within a range such that the ratio of the structural units represented by the general formula (3) and the structural units represented by the general formula (4) in the polymer satisfies the above value.

[0031] The polymer contained in the conductive composition may have only the structural unit represented by the general formula (3) and / or the structural unit represented by the general formula (4). Therefore, when the total structural units of the polymer are taken as 100 mol%, the upper limit of the proportion of the structural unit represented by the general formula (3) and the structural unit represented by the general formula (4) is 100 mol%.

[0032] The polymer contained in the conductive composition has 3 or more and 200 or less repeats of the structural unit represented by the general formula (3) and / or the structural unit represented by the general formula (4).

[0033] Examples of dopants contained in the conductive composition include aromatic sulfonic acids such as benzenesulfonic acid or derivatives thereof, naphthalenesulfonic acid or derivatives thereof, and anthraquinonesulfonic acid or derivatives thereof; sulfosuccinic acid or esters thereof; and polymeric sulfonic acids.

[0034] Examples of benzenesulfonic acid derivatives in benzenesulfonic acid or its derivatives include toluenesulfonic acid, ethylbenzenesulfonic acid, propylbenzenesulfonic acid, butylbenzenesulfonic acid, dodecylbenzenesulfonic acid, methoxybenzenesulfonic acid, ethoxybenzenesulfonic acid, propoxybenzenesulfonic acid, butoxybenzenesulfonic acid, phenolsulfonic acid, cresolsulfonic acid, and benzenedisulfonic acid. Examples of naphthalenesulfonic acid derivatives in naphthalenesulfonic acid or its derivatives include naphthalenedisulfonic acid, naphthalenetrisulfonic acid, methylnaphthalenesulfonic acid, ethylnaphthalenesulfonic acid, propylnaphthalenesulfonic acid, and butylnaphthalenesulfonic acid. Examples of anthraquinonesulfonic acid derivatives in anthraquinonesulfonic acid or its derivatives include anthraquinonedisulfonic acid and anthraquinonetrisulfonic acid. These aromatic sulfonic acids have a molecular weight of 450 or less, and among them, toluenesulfonic acid, methoxybenzenesulfonic acid, phenolsulfonic acid, naphthalenesulfonic acid, and naphthalenetrisulfonic acid are particularly preferred.

[0035] Examples of sulfosuccinic acid or its esters include sulfosuccinic acid, lauryl sulfosuccinic acid, dioctyl sulfosuccinic acid, etc. Among these, dioctyl sulfosuccinic acid is particularly preferred.

[0036] Examples of polymeric sulfonic acids include polystyrene sulfonic acid, sulfonated polyester, phenolsulfonic acid novolac resin, etc. These polymeric sulfonic acids preferably have a weight average molecular weight of 5,000 or more.

[0037] The content of the dopant in the conductive composition may be any amount that can ensure the desired conductivity, and may be, for example, any amount that is contained in the conductive composition when the conductive composition is produced in such a manner that the ratio of the monomer to the dopant is satisfied as explained in the method for producing the conductive composition described below (the method for polymerizing the above polymer).

[0038] Next, the 3,4-ethylenedioxythiophene derivative of the present invention and a method for producing a conductive composition will be described. Hereinafter, the 3,4-ethylenedioxythiophene derivative of the present invention, i.e., the 3,4-ethylenedioxythiophene derivative represented by the general formula (1) above and the 3,4-ethylenedioxythiophene derivative represented by the general formula (2) above, may be collectively referred to as "Si-EDOT." Hereinafter, the polymer having a structural unit represented by the general formula (3) above in the molecule and the polymer having a structural unit represented by the general formula (4) above in the molecule, which constitute the conductive composition of the present invention, may be collectively referred to as "P(Si-EDOT)."

[0039] The present inventors have investigated methods for obtaining the 3,4-ethylenedioxythiophene derivative of the present invention by introducing a substituent having a siloxane bond into the 3,4-ethylenedioxythiophene skeleton, and as a result have found the following synthesis method.

[0040] The siloxane bond-containing substituent in the 3,4-ethylenedioxythiophene derivative is introduced by reacting a hydrosilane with a 3,4-ethylenedioxythiophene precursor, a synthetic intermediate having a terminal carbon-carbon double bond (hydrosilylation), to form a carbon-silicon bond. The hydrosilane used for hydrosilylation is a hydrosilane having a siloxane bond, and the siloxane bond may be linear, branched, cyclic, or via a carbon atom. The structure of the substituent other than the siloxane bond may be a linear or branched alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkynyl group having 2 to 12 carbon atoms, or a cycloalkyl group having 3 to 12 carbon atoms, or a group composed of the same or different groups consisting of hydrogen. The hydrocarbon substituent other than the siloxane bond is preferably a saturated chain hydrocarbon group or an alkoxy group having 1 to 12 carbon atoms.

[0041] Examples of methods for polymerizing the polymer that constitutes the conductive composition include a method of polymerizing a monohalogenated 3,4-ethylenedioxythiophene derivative of the present invention in the presence of a polar aprotic organic solvent and at least one catalyst composed of a nickel catalyst, a palladium catalyst, and an organometallic amide; a method of polymerizing a dihalogenated 3,4-ethylenedioxythiophene derivative of the present invention in the presence of a Grignard reagent; and a method of polymerizing the 3,4-ethylenedioxythiophene derivative of the present invention by mixing it with an oxidizing agent such as organic iron(III) sulfonate or persulfate.

[0042] The conductive composition of the present invention can be produced by carrying out the above-exemplified polymerization in the presence of the above-exemplified dopant, thereby performing doping simultaneously with polymer synthesis. When producing the conductive composition of the present invention in this manner, the mixing ratio of the 3,4-ethylenedioxythiophene derivative of the present invention to the dopant is preferably 1:0.1 to 1:10 by mass. Alternatively, the conductive composition of the present invention can be produced by doping the polymer obtained by the above-exemplified polymerization by contacting it with a solution containing the above-exemplified dopant using a known method. When producing the conductive composition of the present invention in this manner, it is preferable to contact the obtained polymer with a solution containing the dopant at a concentration of 0.1 to 70% by mass.

[0043] The conductive composition of the present invention has excellent solubility in organic solvents and relatively high conductivity, and therefore can be used in a wide range of applications, such as antistatic agents, transparent electrode materials, electrolytes for electrolytic capacitors, etc. Furthermore, the 3,4-ethylenedioxythiophene derivative of the present invention can form the conductive composition of the present invention. [Example]

[0044] The present invention will be described in detail below based on examples, but the present invention is not limited to these examples.

[0045] Example 1 Synthesis of Si-EDOT In a 100 mL two-necked eggplant flask with a reflux tube, 3,4-dimethoxythiophene (1.44 g, 0.01 mmol, Tokyo Chemical Industry), 3-allyloxy-1,2-propanediol (1.45 g, 0.011 mol), and 0.01 g of p-toluenesulfonic acid were mixed in 50 mL of toluene and heated with stirring at 95 °C for 2 hours. Saturated sodium hydrogen carbonate aqueous solution was added to the reaction solution thus obtained to neutralize it, and it was transferred to a separatory funnel to extract the organic layer. The obtained organic layer was washed with saturated sodium hydrogen carbonate aqueous solution, water, and saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The obtained liquid was purified by silica gel column chromatography (solvent: hexane), and then concentrated and vacuum dried to obtain 1.6 g of the compound represented by the following formula (6) (yield 75%).

[0046]

Chemical formula

[0047] To a mixture of 0.8356 g of the obtained compound and 0.6427 g of pentamethyldisiloxane, 4.5 mg of a 2 mass% concentration xylene solution of a platinum catalyst was added, and the reaction was carried out at 60 °C for 5 hours. After distilling off the excess pentamethyldisiloxane from the obtained reaction product under reduced pressure, the residue was purified using size exclusion chromatography with chloroform as an eluent, and then this eluent was distilled off under reduced pressure using a rotary evaporator to obtain 1.252 g of a product (Si-EDOT) (yield 88%). The structure of the obtained product was such that in the above general formula (1), R 1 was a trimethylene group, R 2 , R 3 , R 4 , R 5 and R 6 were all methyl groups and m = 1.

[0048] Example 2 Production of conductive composition <Synthesis of P(Si-EDOT)>[ 0.5718 g of the product obtained in Example 1 was dissolved in 15 mL of chloroform, to which 0.5652 g of N-bromosuccinimide was added, followed by stirring at room temperature for 30 minutes. The resulting reaction mixture was added to 20 mL of water, and the organic and aqueous layers were separated. The aqueous layer was extracted twice with 20 mL of chloroform. All organic layers were dried over anhydrous sodium sulfate, and the solvent was concentrated to obtain a crude product. This crude product was purified by silica gel column chromatography using hexane as an eluent, yielding 0.6861 g of the dibrominated product (yield 88%).

[0049] 154.6 mg of the dibrominated product synthesized by the above method was dissolved in 0.3 mL of tetrahydrofuran in a glove box. 0.23 mL of a 1.3 M solution of isopropylmagnesium chloride in tetrahydrofuran was added and the mixture was allowed to react at 60 °C for 1 hour. Next, 0.1 mL of a solution containing 3.8 mg of nickel acetylacetonate and 6.7 mg of 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene dissolved in 0.5 mL of tetrahydrofuran and stirred in the glove box for 2 hours was added. The reaction solution was then placed in the glove box and allowed to react at room temperature for 24 hours under an argon atmosphere. The resulting reaction mixture was poured into 1 M aqueous hydrochloric acid to precipitate a solid. The residue was then filtered under suction, washed with methanol and hexane, and dried under reduced pressure to yield 68.8 mg of the polymerization product [P(Si-EDOT)] (64% yield).

[0050] <P(Si-EDOT)のドーピング> 30 mg of the resulting polymerization reaction product [P(Si-EDOT)] was added to 6 mL of chloroform and stirred until complete dissolution was confirmed. 0.2 mL of this solution was applied to a 1 x 1 cm glass substrate. The substrate was then dried under reduced pressure at room temperature for 6 hours. The glass substrate was then immersed in a solution of 56.5 mg of p-toluenesulfonic acid in 30 mL of water for 1 hour, removed, and air-dried for 3 hours. This doped the polymerization reaction product with p-toluenesulfonic acid, resulting in a conductive composition formed as a thin film on the glass substrate.

[0051] When the film thickness of the thin film on the glass substrate was measured using a laser microscope, it was 13 μm. Also, when the conductivity of this thin film was measured using a Loresta, it was 775 S / cm.

[0052] Comparative Example 1 <Synthesis of Si-thiophene> According to the procedures of Examples 1 to 4 of JP-A-2015-30789, the compound (Si-thiophene) represented by the following formula (7) was obtained.

[0053]

Chemical formula

[0054] <Synthesis of P(Si-thiophene)> Using the above compound (Si-thiophene) as a starting material, according to the procedure of Example 5 of JP-A-2015-30789, the compound [P(Si-thiophene)] composed of the structural unit represented by the following formula (8) was obtained.

Chemical formula

[0055] 30 mg of the obtained polymerization reaction product [P(Si-thiophene)] was added to 6 mL of chloroform and stirred. After confirming that it was completely dissolved, except using the solution obtained here, in the same manner as in Example 2, p-toluenesulfonic acid was doped into the above polymerization reaction product [P(Si-thiophene)] to obtain a conductive composition formed in a thin film state on a glass substrate.

[0056] When the film thickness and conductivity of the conductive composition formed in a thin film state on the glass substrate were measured, the film thickness was 10 μm and the conductivity was 1.8×10 -4 S / cm.

[0057] Comparative Example 3 <Synthesis of PEDOT> 0.5 g of 3,4-ethylenedioxythiophene was added to 25 g of a 2% by weight solution of iron p-toluenesulfonate in ethanol, and the mixture was allowed to react at room temperature for 1 hour. The residue obtained by suction filtration was then washed with methanol and hexane, and then dried under reduced pressure to obtain 0.47 g of the polymerization product (PEDOT) (yield 93%).

[0058] 30 mg of the resulting polymerization reaction product (PEDOT) was added to 6 mL of chloroform and stirred, but it was confirmed that it was hardly dissolved.

Claims

1. A 3,4-ethylenedioxythiophene derivative characterized by being represented by the following general formula (1) or (2): 【Chemistry 1】 [In the above general formula (1), R １ is a linear or branched, substituted or unsubstituted alkylene group having 2 to 6 carbon atoms, and R ２ and R ３ are each a linear or branched alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkynyl group having 2 to 12 carbon atoms, or a cycloalkyl group having 3 to 12 carbon atoms, which may contain a silicon-oxygen bond and has a dialkyl group on the silicon; R ４ , R ５ and R ６ are the same or different groups each consisting of a linear or branched alkoxy group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkynyl group having 2 to 12 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, or hydrogen, and m is R ２ , R ３ are the same or different groups and are a number from 2 to 6 representing the number of repeating silicon-oxygen bond units. 【Chemistry 2】 [In the above general formula (2), R ７ is a linear or branched, substituted or unsubstituted alkylene group having 2 to 6 carbon atoms, and R ８ and R ９ are each a linear or branched alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkynyl group having 2 to 12 carbon atoms, or a cycloalkyl group having 3 to 12 carbon atoms, which may contain a silicon-oxygen bond and has a dialkyl group on the silicon; R １０ , R １１ and R １２ are the same or different groups each consisting of a linear or branched alkoxy group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkynyl group having 2 to 12 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, or hydrogen, and n is R ８ , R ９ are the same or different groups and are a number from 2 to 6 representing the number of repeating silicon-oxygen bond units.

2. A conductive composition comprising a polymer having a structural unit represented by the following general formula (3) or (4) in the molecule, and a dopant: 【Transformation 3】 [In the above general formula (3), R １ is a linear or branched, substituted or unsubstituted alkylene group having 2 to 6 carbon atoms, and R ２ and R ３ are each a linear or branched alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkynyl group having 2 to 12 carbon atoms, or a cycloalkyl group having 3 to 12 carbon atoms, which may contain a silicon-oxygen bond and has a dialkyl group on the silicon; R ４ , R ５ and R ６ are the same or different groups each consisting of a linear or branched alkoxy group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkynyl group having 2 to 12 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, or hydrogen, and m is R ２ , R ３ are the same or different groups and are a number from 2 to 6 representing the number of repeating silicon-oxygen bond units. 【Chemistry 4】 [In the above general formula (4), R ７ is a linear or branched, substituted or unsubstituted alkylene group having 2 to 6 carbon atoms, and R ８ and R ９ are each a linear or branched alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkynyl group having 2 to 12 carbon atoms, or a cycloalkyl group having 3 to 12 carbon atoms, which may contain a silicon-oxygen bond and has a dialkyl group on the silicon; R １０ , R １１ and R １２ are the same or different groups each consisting of a linear or branched alkoxy group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkynyl group having 2 to 12 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, or hydrogen, and n is R ８ , R ９ are the same or different groups and are a number from 2 to 6 representing the number of repeating silicon-oxygen bond units.

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