TW201805322A - Polyvalent alkyne compound, method for producing the same and use thereof - Google Patents

Abstract

The present invention provides a polyvalent alkyne compound which is excellent in heat resistance, a heat convertible resin composition, a heat curing and an insulating material. The polyvalent alkyne compound represented by the following formula 1 contains the aromatic hydrocarbon atoms with a high proportion, so that the heat curing which is excellent in heat resistance is obtained by carrying out the heating curing on the heat convertible resin composition containing the polyvalent alkyne compound. In the formula 1, Ar1 is an aromatic hydrocarbon which can have 1 to 3 hydrocarbon substituent groups having 1 to 6 carbons and of which the carbon number is 6 to 30; X1 is an alkyl which has the aromatic hydrocarbon atoms of which the carbon number is 6 to 18 and of which the carbon number is 6 to 30, n is an integer of 1 to 10, A is a structure or the hydrogen represented by the formula 2, and more than 50% of the A has the structure represented by the formula 2.

Description

Polyalkyne compound and its preparation method and use

The present invention relates to a polyalkyne compound having good heat resistance, and a method for preparing the same and use thereof.

The thermosetting resin composition has properties such as fluidity before heat curing and strong properties after heat curing, and can be used as an excellent molding material. Among them, epoxy resins have the advantages of high adhesiveness, diversity, and favorable price, and therefore have been widely used in various industries as representative thermosetting resin compositions for many years.

Today, in various industries, from the viewpoint of environmental protection and the like, in order to meet these requirements, the heat resistance of the thermosetting resin composition used as a molding material must be improved. Epoxy resins that have been used as suitable thermosetting resins for molding materials in various industries until now have the following characteristics: glycidyl groups have become an important cause of reduced thermal decomposition resistance; on the other hand, if the concentration of glycidyl groups is reduced, vitrification The transition temperature is liable to decrease. Therefore, applications with high requirements that cannot be met with conventional general-purpose epoxy resins have begun to appear. The high requirements are related to the properties required for thermosetting resins, that is, the properties of good thermal decomposition resistance and high glass transition temperature. Claim. Therefore, based on the A novel thermosetting resin composition with different design ideas.

For example, in order to meet the demand for high-speed communication in recent years, various thermosetting resin compositions have been proposed (Patent Document 1, Patent Document 2). On the other hand, from the viewpoint of environmental protection, with the trend toward full electrification of automobiles, power devices have attracted attention. Since its use temperature also reaches 200 ° C or higher, it is difficult to obtain a thermosetting product having sufficient heat resistance by using a thermosetting resin composition containing an epoxy-based material containing a conventional epoxy resin as a main component.

[Prior technical literature]

[Patent Literature]

Patent Document 1: Japanese Patent Publication No. 2004-504455.

Patent Document 2: Japanese Patent Laid-Open No. 2006-265513.

Patent Literature 1 and Patent Literature 2 describe thermosetting resin compositions having an alkynyl group for the purpose of reducing the dielectric constant. However, the thermosetting resin compositions described in these patent documents all reduce the dielectric structure by reducing the aromatic structure and increasing the aliphatic structure. Constant method. Therefore, even if these thermosetting resin compositions are used, a thermosetting material having sufficiently excellent heat resistance cannot be obtained, and the aforementioned sufficiently excellent heat resistance is heat resistance to a degree that can satisfy high requirements related to heat resistance in recent years.

Therefore, an object of the present invention is to provide a polyhydric alkyne compound, a thermosetting resin composition, a thermosetting material, and an insulating material that are superior in heat resistance to conventionally used epoxy resins and are particularly suitable for use under high temperature conditions.

The present invention includes a configuration specified by the following items as a method for solving the above-mentioned problems.

[1] A polyacetylene compound represented by the formula (1).

In the formula (1), Ar ¹ is an aromatic hydrocarbon group having 6 to 30 carbon atoms and may have 1 to 3 carbon substituents having 1 to 6 carbon atoms; X ¹ is an aromatic hydrocarbon group having 6 to 18 carbon atoms. A hydrocarbon group having a carbon number of 6 to 30; n is an integer of 1 to 10; A is a structure represented by formula (2) or hydrogen, and 50% or more of A has a structure represented by formula (2).

In formula (2), R ¹ and R ² are a hydrogen atom or a hydrocarbon group having 1 to 6 carbon atoms.

[2] The polyalkyne compound according to [1], wherein X ¹ is represented by formula (3) or formula (4).

[3] The polyacetylene compound according to [1] or [2], wherein the melt viscosity at 150 ° C is 10 mPa. s to 500mPa. s.

[4] A method for producing a polyvalent alkyne compound as described in [1], [2], or [3] The method for producing a alkyne compound includes a reaction step of reacting a polyhydric phenol compound represented by the formula (5) with an alkyne compound represented by the formula (6).

In formula (5), Ar ¹ is an aromatic hydrocarbon group having 6 to 30 carbon atoms and may have 1 to 3 carbon substituents having 1 to 6 carbon atoms; X ¹ is an aromatic hydrocarbon group having 6 to 18 carbon atoms. A hydrocarbon group has a carbon number of 6 to 30; n is an integer of 1 to 10.

In the formula (6), R ¹ and R ² are a hydrogen atom or a hydrocarbon group having 1 to 6 carbon atoms, and Y is Cl, Br, I, or an alkoxy group having 1 to 4 carbon atoms.

[5] A thermosetting resin composition containing the polyacetylene as described in [1], [2], or [3] Compound.

[6] The thermosetting resin composition according to [5], which contains an olefin compound having two or more alkenyl groups in one molecule.

[7] The thermosetting resin composition according to [6], wherein the ene compound is a maleimide compound represented by formula (7).

In formula (7), Ar ² is a hydrocarbon group having 6 to 30 carbons, which may have 1 to 3 carbon substituents having 1 to 6 carbons; X ² is a hydrocarbon group having 1 to 6 carbons, O, S, SO ₂ Or a direct bond between Ar ² and Ar ² ; m is an integer from 1 to 10.

[8] The thermosetting resin composition according to [5], [6] or [7], which contains a curing accelerator.

[9] The thermosetting resin composition according to [8], wherein the curing accelerator is selected from the group consisting of transition metal compounds, peroxides, azo compounds, phosphines, amidines, tertiary amines, amidines, and imidazoles. One or more of the ethnic groups formed.

[10] A thermosetting product obtained by thermally curing the thermosetting resin composition according to any one of [5] to [9].

[11] An insulating material comprising the thermosetting resin composition according to any one of [5] to [9].

[12] The use of an insulating material is the use of the insulating material according to [11] as a sealing material, a substrate material, a chip bonding agent, or a solder resist.

Since the polyhydric acetylene resin of the present invention has an aromatic ring as a cross-linking group, the thermosetting resin composition containing the polyhydric acetylene resin is thermally cured to obtain a thermosetting material having excellent heat resistance.

Hereinafter, embodiments of the present invention as a polyalkyne compound, a method for producing a polyalkyne compound, a thermosetting resin composition, and a thermosetting product will be described.

(Polyyne compound)

In the polyacetylene compound of this embodiment, 50% to 100% of A in formula (1) It has a structure represented by Formula (2). In this embodiment, the formulas (1) to (7) represent the formulas (1) to (7) described in the means for solving the problem.

In formula (1), 50% or more of A bonded to Ar ¹ via an oxygen atom O is a structure represented by formula (2), thereby suppressing polyhydric alkyne caused by a hydrogen bond caused by a hydroxyl group when A is hydrogen An increase in the compound's melt viscosity. Therefore, it can be suitably used as a molding material which requires high fluidity before molding. From the viewpoint of reducing the viscosity of the polyalkyne compound, the structure represented by formula (2) in A of formula (1) is preferably 50% to 100%, more preferably 70% to 100%, and even more preferably 90% to 100%.

X ¹ in Formula (1) is preferably a structure represented by Formula (3) or Formula (4). By increasing the proportion of an aromatic ring such as a benzene ring contained in the polyhydric alkyne compound, the glass transition temperature and thermal decomposition resistance of the thermosetting product obtained by curing the thermosetting resin composition containing the polyalkyne compound can be improved. In the description of the present invention, if the glass transition temperature and thermal decomposition resistance of a thermosetting material are high, and it is suitable for use under high temperature conditions, it is referred to as "high heat resistance".

By reducing the melt viscosity of the polyalkyne compound, the melt viscosity of the thermosetting resin composition containing the polyalkyne compound also becomes low. Thereby, the fluidity | liquidity of the thermosetting resin composition at the time of shaping | molding becomes favorable, and a thermosetting body can be shape | molded using various shaping | molding methods. From the viewpoint of improving the operability of transfer molding or injection molding that requires high fluidity for the molding material, the polyacetylene compound used as the molding material has a better melt viscosity at 150 ° C. 10mPa. s to 500mPa. s, more preferably 10mPa. s to 250mPa. s, more preferably 10 mPa. s to 150mPa. s. The melt viscosity refers to a value measured using an ICI (Investment Casting Institute) cone plate viscometer (manufactured by MST Engineering Co., Ltd.).

(Manufacturing method of polyacetylene compound)

The polyhydric alkyne compound of this embodiment has a reaction step of reacting a polyhydric phenol compound represented by the formula (5) with an alkyne compound represented by the formula (6). From the viewpoint of obtaining a polyhydric alkyne compound having a low viscosity with the use of the minimum alkyne compound, the ratio of the hydroxyl equivalent of the polyhydric phenol compound to the halogen equivalent of the alkyne compound, that is, the hydroxyl equivalent / halogen equivalent is preferably 1 / 0.5 To 1/5, more preferably 1 / 0.8 to 1/3, and still more preferably 1/1 to 1 / 1.5.

In the aforementioned reaction step, a general-purpose solvent such as acetone or methyl ethyl ketone can be used as a solvent used when the polyhydric phenol compound and the alkyne compound are reacted. The amount of the solvent used in the reaction step is not particularly limited. The preferred temperature for the reaction step varies depending on the type of solvent used. From the viewpoint of maintaining the triple bond of the alkyne compound, it is preferably 40 ° C to 150 ° C, more preferably 50 ° C to 120 ° C, and It is preferably 60 ° C to 80 ° C.

In the aforementioned reaction step, a basic component may be contained in the aforementioned reaction solvent. As Examples of the basic component include sodium hydroxide, potassium hydroxide, anhydrous potassium carbonate, pyridine, triethylamine, and imidazole.

(Thermosetting resin composition)

This invention can also be implemented as a thermosetting resin composition containing the said polyhydric alkyne compound. From the viewpoint of improving the moldability (low melt viscosity, high fluidity) at the time of curing the thermosetting resin composition and improving the heat resistance of the thermosetting thermosetting product, the content of the polyvalent acetylene compound is less than Out of 100 parts by mass of the thermosetting resin composition, 2 to 80 parts by mass is preferred, 5 to 50 parts by mass is more preferred, and 8 to 30 parts by mass is still more preferred.

A multi-bond monomer having a structure different from that of a polyhydric alkyne compound can be blended in a thermosetting resin composition containing a polybasic alkyne compound. Accordingly, a plurality of characteristics derived from other types of monomers can be imparted to a thermosetting product obtained by thermally curing a thermosetting resin composition without impairing the originally high heat resistance performance of the polyacetylene compound. Depending on the type of the multiple-bond-type monomer, a hydroxyl group represented by A in formula (1) as hydrogen may play an important role in the polymerization reaction. For example, when the thermosetting resin composition contains epoxy resin as another kind of monomer, the hydroxyl group in the polyalkyne compound represented by formula (1) functions as an epoxy resin curing agent. Therefore, from this point of view, that is, from the viewpoint of imparting a plurality of characteristics to the thermosetting material, it can be said that it is preferable that A in the formula (1) does not have all the structure represented by the formula (2), but also includes A A hydroxyl group in a hydrogen structure.

(Curing accelerator)

The said thermosetting resin composition may further contain a hardening accelerator. Examples of the curing agent include transition metal compounds, peroxides, azo compounds, phosphines, amidines, tertiary amines, amidines, and imidazoles. They can be used alone or in combination. Examples of the transition metal compound include cobalt (III) acetoacetone, tetrakis (triphenylphosphine) palladium (0), and tris (triphenylphosphine) rhodium (I) chloride. Examples of the peroxide include: Out: benzamidine peroxide, dicumyl peroxide; examples of azo compounds include azobisisobutyronitrile; examples of phosphines include triphenylphosphine, tris (methylphenyl) ) Phosphine, tributylphosphine, tricyclohexylphosphine; Examples of fluorenes include triphenylphosphonium phenate, tetraphenylphosphonium tetraphenylborate, tetraphenylphosphonium tetranaphthalate borate; as tertiary amines Examples include tributylamine, dimethylbenzylamine, diazabicycloundecene, 1,4-diazabicyclo [2.2.2] octane; examples of hydrazones include diaza Bicycloundecene; Examples of imidazoles include 2-methylimidazole, 2,4-dimethylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 2-phenyl- 4-methylimidazole and the like.

(Other resin components)

The thermosetting resin composition of this embodiment may contain other resin components other than the said polyhydric alkyne compound. Examples of other resin components include epoxy compounds and olefin compounds having two or more alkenyl groups in one molecule. Examples of the olefin compound include a maleimide compound represented by the formula (7).

The thermosetting resin composition contains a resin other than the polyhydric alkyne compound described above. In the case of scoring, from the viewpoint of imparting a high heat resistance derived from a polyhydric acetylene compound to a thermosetting product obtained by heat curing, the content of a resin component other than the polyhydric acetylene compound is preferably 100 parts by mass of the polyhydric acetylene compound. 5 to 75 parts by mass, more preferably 8 to 50 parts by mass, and even more preferably 10 to 25 parts by mass.

(Other ingredients)

To the thermosetting resin composition of this embodiment, an inorganic filler, a coupling agent, a release agent, a colorant, a flame retardant, a low-stress agent, and the like are added as necessary. Moreover, they can also be used after reacting in advance.

Examples of the inorganic filler include amorphous silicon dioxide, crystalline silicon dioxide, alumina, glass, calcium silicate, magnesite, clay, talc, mica, magnesium oxide, barium sulfate, and the like. Preferred are amorphous silicon dioxide, crystalline silicon dioxide, and barium sulfate. Furthermore, when it is desired to maintain the excellent moldability and increase the blending amount of the inorganic filler, it is preferable to use a spherical inorganic filler having a wide particle size distribution that can be finely packed.

Examples of the coupling agent include silane coupling agents such as mercaptosilane, vinyl silane, amino silane, and epoxy silane, and titanium coupling agents. Examples of the release agent include carnauba wax. , Paraffin, and the like; examples of the colorant include carbon black and the like. Examples of flame retardants include phosphorus compounds and metal hydroxides. Examples of low-stress agents include silicone rubber, modified nitrile rubber, and modified butadiene. Rubber, modified silicone oil, etc.

As a general method when the thermosetting resin composition of the present embodiment is prepared as a molding material, the following method can be mentioned: for example, after mixing each raw material in a predetermined ratio with a stirrer, kneading with a heat roller or kneader or the like is applied. It is processed, further cooled and solidified, and then pulverized into an appropriate size, and if necessary, is tabletized. The thus-obtained molding material can be used to seal a semiconductor, for example, using low-pressure transfer molding or the like, thereby manufacturing a semiconductor device. The curing of the epoxy resin composition can be performed, for example, in a temperature range of 100 ° C to 250 ° C.

Examples of the thermosetting product obtained by curing the thermosetting resin composition of the present embodiment include a resin film that is cured by heating the thermosetting resin composition as a varnish, or a thermosetting product that is cured by heating a prepreg. In the varnish, a general-purpose solvent such as acetone or methyl ethyl ketone can be used as a solvent for the resin component, and the amount of the solvent to be blended is not particularly limited.

The prepreg refers to a semi-cured state in which a thermosetting resin composition is made into a varnish, immersed in a substrate, and heated or dried. As a base material, glass cloth, carbon fiber, etc. can be used.

The thermosetting material of this embodiment can be used as an insulating material. The insulating material can be used as a sealing material (underfill material), a substrate material, a chip bonding agent, and a solder resist. The sealing material is a material that prevents a component constituting a circuit board from coming into contact with outside air by sealing a gap.

[Example]

Hereinafter, examples and comparative examples of the present invention will be described. Each embodiment illustrates the technical scope of the present invention according to specific examples, and does not limit the technical scope in specific disclosure. In the following description, unless otherwise specified, "part" means "mass part", "%" means "mass%", and the temperature of the liquid in each step means room temperature (about 25 ° C).

[Example 1]

79.1 g of a phenol aralkyl resin having a structure represented by formula (3) ("HE100C-30" manufactured by Air Water Corporation, 176 g / eq of hydroxyl equivalent), 76.3 g of anhydrous potassium carbonate, 65.7 g of propargyl bromide, and acetone 460 g was charged into a 1 L autoclave, and it was kept for 15 hours while stirring at 90 ° C. After cooling, the acetone solution was recovered by filtration, and the acetone was removed at 90 ° C and 30 Torr to obtain 89.4 g of monomer A, that is, X ¹ in the formula (1) is represented by a polyvalent alkyne compound of the formula (3).

The melt viscosity at 150 ° C was measured with an ICI cone-plate viscometer (manufactured by MST Engineering Co., Ltd.), and the result was 143 mPa. s. In addition, the hydroxyl equivalent calculated by the acetylation back-titration method was 2962 g / eq, and the propargylation rate (A in the formula (1) has the formula (2) The calculated ratio of the structure shown) was 93%. That is, the following monomer A was obtained, that is, a polyhydric alkyne compound having a structure represented by Formula (2) in which 93% of A in the polyalkyne compound represented by Formula (1) was obtained.

[Example 2]

94.6 g of a phenol biphenylaralkyl resin having a structure represented by the formula (3) ("HE200C-10" manufactured by Air Water Co., Ltd., hydroxy equivalent 206 g / eq), 76.3 g of anhydrous potassium carbonate, and propargyl 65.7 g of bromine and 460 g of acetone were put into a 1-L autoclave, and kept for 15 hours while stirring at 90 ° C. After cooling, the acetone solution was recovered by filtration, and the acetone was removed at 90 ° C. and 30 Torr to obtain 106.9 g of monomer B, that is, X ¹ in the formula (1) is represented by a polyvalent alkyne compound of the formula (4).

Using an ICI cone-plate viscometer to measure its melt viscosity at 150 ° C, the result was 33 mPa. s. In addition, the hydroxyl equivalent calculated by the acetylation back titration method was 3592 g / eq, and the calculation result of the propargylation rate was 93%. That is, a monomer B, that is, a polyhydric alkyne compound having a structure represented by Formula (2) in which 93% of A in the polyalkyne compound represented by Formula (1) was obtained.

[Example 3]

The monomer A, which is a polyhydric alkyne compound, and cobalt (III) acetoacetone, which is a curing accelerator, are blended at a ratio shown in Table 1 to homogeneously mix and disperse, thereby obtaining a melt viscosity at 150 ° C (using an ICI cone plate Viscometer for measurement) was 144mPa. s thermosetting resin group Resin composition. This was heated at 180 ° C. for 6 hours, and then heated at 230 ° C. for 6 hours to perform thermal curing to prepare a test sample as a thermosetting product of the thermosetting resin composition of the present invention. Using the test sample, the glass transition temperature and the 5% weight reduction temperature were measured, and the heat resistance of the thermosetting product was evaluated. The results are shown in Table 1.

[Example 4]

The monomer B, which is a polyacetylene compound, and cobalt (III) acetoacetone, which is a curing accelerator, are blended in a ratio shown in Table 1 to homogeneously mix and disperse, thereby obtaining a melt viscosity at 150 ° C. (using an ICI cone plate Viscometer for measurement) 33mPa. Resin composition of thermosetting resin composition. Using the points described in Example 3, this was prepared and evaluated as a test sample of a thermosetting resin as a thermosetting resin composition. The results are shown in Table 1.

[Example 5]

Blend monomer B as a polyhydric alkyne compound, 4,4'-diphenylmethane bismaleimide as a maleimide compound, and triphenylphosphine as a curing accelerator in a ratio shown in Table 1. The mixture was homogeneously mixed and dispersed to obtain a melt viscosity (measured with an ICI cone-plate viscometer) at 150 ° C of 40 mPa. s' resin composition. Using the points described in Example 3, this was prepared and evaluated as a test sample of a thermosetting resin as a thermosetting resin composition. The results are shown in Table 1.

[Example 6]

Using only monomer B, that is, the melt viscosity at 150 ° C (measured with an ICI cone-plate viscometer) was 33 mPa. The polyacetylene of s was prepared and evaluated as the test sample of the thermosetting resin composition of a thermosetting resin composition by the point described in Example 3. The results are shown in Table 1.

[Comparative Example 1]

The epoxy resin represented by the following formula (8) ("NC3000" manufactured by Nippon Kayaku Co., Ltd., with an epoxy equivalent of 275 g / eq) and the curing agent (AIR represented by the following formula (9) were blended at a ratio shown in Table 1. WATER company manufactured "HE200C-10" with a hydroxyl equivalent of 206 g / eq) and triphenylphosphine, which were homogeneously mixed and dispersed, thereby obtaining a melt viscosity (measured with an ICI cone-plate viscometer) at 150 ° C of 148 mPa. s' resin composition. Hereinafter, a test sample as a thermosetting material of an epoxy resin composition (thermosetting resin composition) was prepared and evaluated in the same manner as in Example 3. The evaluation results are shown in Table 2.

In the formula (8), G represents a glycidyl group, and m represents a natural number of 1 to 10.

[Formula (9)]

In Formula (9), n represents a natural number of 1 to 10.

(Evaluation method)

(1) Glass transition temperature

Using a TMA (Thermomechanical Analyzer), a test sample of a thermosetting resin composition as a thermosetting resin composition was heated under a nitrogen atmosphere at a temperature increase rate of 10 ° C./minute, and the inflection point of the linear expansion curve was used as the glass transition. temperature.

(2) 5% weight reduction temperature

Using a TGA (Thermogravimetric Analyzer; thermogravimetric analyzer), a test sample of a thermosetting resin composition as a thermosetting resin composition was heated at a temperature increase rate of 10 ° C./minute in a nitrogen atmosphere, and the temperature at which the initial weight was reduced by 5% was measured. Temperature reduction as 5% weight.

The polyalkyne compounds of Examples 1 and 2 have lower melt viscosity than known epoxy-based materials. Therefore, it is useful as a raw material for a molding material that requires high fluidity.

The thermosetting resins of Examples 3 to 6 obtained by thermosetting the thermosetting resin composition containing the thermosetting monomer of the polyvalent alkyne compound of the present invention and the thermosetting resin composition containing the epoxy resin are thermosetting. Compared with the obtained thermosetting product of Comparative Example 1, both had a higher glass transition temperature and a 5% mass reduction temperature, and had higher heat resistance. Therefore, the present invention can be suitably used for applications requiring high heat resistance.

[Industrial availability]

By using the polyacetylene compound of the present invention, a heat-cured material having high heat resistance can be provided. Therefore, the polyalkyne compound can be used in applications such as insulating materials that require high insulation properties. Various uses such as solder resist. At the same time, it is possible to achieve both the multifunctionalization of monomers that have been difficult to solve during the high heat resistance of conventional epoxy resin curing agents and the high flow during molding.

In addition, the present invention can also easily introduce a phenolic hydroxyl group to make it function as an epoxy resin curing agent. It can be used not only as a novel material with higher heat resistance than conventional epoxy-based materials, but also can be combined with existing materials. Use of epoxy-based materials as a mean Material, that is, a raw material having a moderate heat resistance.

Claims (12)

A polyalkyne compound represented by formula (1):

In the formula (1), Ar ¹ is an aromatic hydrocarbon group having 6 to 30 carbon atoms and may have 1 to 3 carbon substituents having 1 to 6 carbon atoms; X ¹ is an aromatic hydrocarbon group having 6 to 18 carbon atoms. A hydrocarbon group having a carbon number of 6 to 30; n is an integer of 1 to 10; A is a structure represented by formula (2) or hydrogen, and 50% or more of A has a structure represented by formula (2);

In formula (2), R ¹ and R ² are a hydrogen atom or a hydrocarbon group having 1 to 6 carbon atoms. The polyalkyne compound according to claim 1, wherein X ¹ is represented by formula (3) or formula (4):

The polyalkyne compound as described in claim 1 or 2, wherein the melt viscosity at 150 ° C is 10 mPa. s to 500mPa. s. A method for producing a polyhydric alkyne compound, which is the method for producing a polyhydric alkyne compound according to claim 1, 2 or 3, which comprises a polyhydric phenol compound represented by formula (5) and an alkyne compound represented by formula (6) Reaction steps for the reaction:

In formula (5), Ar ¹ is an aromatic hydrocarbon group having 6 to 30 carbon atoms and may have 1 to 3 carbon substituents having 1 to 6 carbon atoms; X ¹ is an aromatic hydrocarbon group having 6 to 18 carbon atoms. A hydrocarbon group having a carbon number of 6 to 30; n is an integer from 1 to 10;

In the formula (6), R ¹ and R ² are a hydrogen atom or a hydrocarbon group having 1 to 6 carbon atoms, and Y is Cl, Br, I, or an alkoxy group having 1 to 4 carbon atoms. A thermosetting resin composition containing a polyhydric alkyne compound according to claim 1, 2 or 3. The thermosetting resin composition according to claim 5, which contains an olefin compound having two or more alkenyl groups in one molecule. The thermosetting resin composition according to claim 6, wherein the olefinic compound is a maleimide compound represented by formula (7):

In the formula (7), Ar ² is an aromatic hydrocarbon group having 6 to 30 carbon atoms and may have a hydrocarbon substituent having 1 to 3 carbon atoms having 1 to 6 carbon atoms; X ² is a hydrocarbon group having 1 to 6 carbon atoms, O, and S , SO ₂ or Ar ² is a direct bond to Ar ² ; m is an integer from 1 to 10. The thermosetting resin composition according to claim 5, 6, or 7, which contains a curing accelerator. The thermosetting resin composition according to claim 8, wherein the curing accelerator is selected from the group consisting of transition metal compounds, peroxides, azo compounds, phosphines, amidines, tertiary amines, amidines, and imidazoles. One or more of the ethnic groups. A thermosetting product is obtained by thermally curing the thermosetting resin composition according to any one of claims 5 to 9. An insulating material comprising the thermosetting resin composition according to any one of claims 5 to 9. The use of an insulating material is the use of the insulating material according to claim 11 as a sealing material, a substrate material, a die bonding agent, or a solder resist.