Composition for thermally conductive material, thermally conductive material, article, and electronic component

Abstract

A composition for a thermally conductive material is provided, the composition containing a compound represented by formula (1). In the formula, R1 to R6 each independently represent a group represented by formula (2) or an alkyl group, and at least three of R1 to R6 are groups represented by formula (2). In the formula, R11 represents an alkyl group or an alkenyl group and p is 1 or 2.

Description

Composition for thermally conductive material, thermally conductive material, article, and electronic component

[0001] The present invention relates to a composition for a thermally conductive material, a thermally conductive material, an article, and an electronic component.

[0002] In electronic components such as processors and power modules, heat is generated during operation. To protect such electronic components from heat, a means for efficiently dissipating the generated heat is required. Thermal interface materials (TIMs) are materials that are placed between a heat source and a heat sink, etc., to reduce the thermal resistance between the heat source and the heat sink and promote heat conduction from the heat source.

[0003] In recent years, organic thermally conductive materials without inorganic fillers have been investigated as TIMs for thin film structures. Specifically, as disclosed in Non-Patent Documents 1 and 2, discotic liquid crystal polymer films are known to exhibit high in-plane thermal conductivity. Such discotic liquid crystal polymer films are expected to be used as heat spreaders that diffuse heat in-plane by controlling the molecular orientation in a specific direction using a magnetic field or the like, thereby exhibiting a specifically high thermal conductivity (anisotropic thermal conductivity) in the in-plane direction of the film. Because the thermal conductivity in the thickness direction is extremely low and acts as an adiabatic, heat transfer performance to a heat sink that dissipates heat from a heat source to the outside cannot be expected.

[0004] "Highly anisotropic thermal conductivity of discotic nematic liquid crystalline films with homeotropic alignment", Dong-Gyun Kim, Yun Ho Kim, Tae Joo Shin, Eun Jung Cha, Da SomKim, Byoung Gak Kim, Youngjae Yoo, Yong Seok Kim, Mi Hye Yi and Jong ChanWonab, Chem. Commun., 2017, 53, 8227-8230"Heat Transfer Organic Materials: Robust Polymer Films with the Outstanding Thermal Conductivity Fabricated by the Photopolymerization of Uniaxially Oriented Reactive Discogens", Dong-Gue Kang, Minwook Park, Dae-Yoon Kim, Munju Goh, Namil Kim and Kwang-UnJeong, ACS Appl. Mater. Interfaces 2016, 8, 30492-30501

[0005] An object of one aspect of the present invention is to provide a composition capable of forming a novel thermally conductive material having anisotropic thermal conductivity.

[0006] The inventors discovered that by introducing cinnamic acid moieties into the triphenylene skeleton, which is the core moiety, the carbon-carbon double bonds contained in the cinnamic acid moieties react with each other to form a ring, and the molecules are fixed at positions close to the core moiety, resulting in the development of anisotropic thermal conductivity due to the highly ordered columnar structure.

[0007] The present invention includes the following aspects: [1] A composition for a thermally conductive material, comprising a compound represented by the following formula (1): In the formula, R １ ~R ６ are each independently a group represented by the following formula (2) or an alkyl group, and R １~R ６ At least three of the above are groups represented by formula (2). In the formula, R １１ represents an alkyl group or an alkenyl group, and p is 1 or 2. [2] The composition for a thermally conductive material according to [1], wherein the group represented by formula (2) is a group represented by the following formula (2-1): In the formula, p is 1 or 2, and each m independently represents an integer of 5 to 15. [3] The composition for thermally conductive materials according to [1], wherein the group represented by formula (2) is a group represented by the following formula (2-3): [In the formula, each m independently represents an integer of 5 or more and 15 or less.] [4] The composition for a thermally conductive material according to any one of [1] to [3], further containing a polymerization initiator. [5] A thermally conductive material formed from the composition for a thermally conductive material according to any one of [1] to [3]. [6] An article comprising a heat source and the thermally conductive material according to [5] in thermal contact with the heat source. [7] An electronic component comprising a semiconductor component, a heat sink, and a thermally conductive material provided between the semiconductor component and the heat sink, wherein the thermally conductive material comprises the thermally conductive material according to [5].

[0008] According to one aspect of the present invention, a composition capable of forming a novel thermally conductive material having anisotropic thermal conductivity can be provided. According to another aspect of the present invention, when a thermally conductive material in the form of a film is formed, high thermal conductivity is obtained in the thickness direction of the film, and high thermal conductivity is also obtained in the in-plane direction of the film (direction perpendicular to the thickness direction). According to another aspect of the present invention, a [2+2] cyclization reaction of the cinnamic acid moiety in the compound represented by formula (1) is utilized, thereby achieving an appropriate crosslink density in the thermally conductive material. According to another aspect of the present invention, a liquid crystal phase can be formed using a single component of the compound represented by formula (1), making it easy to predict and maintain the liquid crystal phase.

[0009] 1 is a schematic cross-sectional view showing an embodiment of an article;

[0023] FIG. 2 is a schematic cross-sectional view showing an enlarged essential part of the article shown in FIG.

[0010] A composition for a thermally conductive material according to one embodiment of the present invention (hereinafter also simply referred to as "composition") contains a compound represented by the following formula (1). In the formula, R １ ~R ６ are each independently a group represented by the following formula (2) or an alkyl group. In the formula, R １１ is an alkyl or alkenyl group, and p is 1 or 2.

[0011] R in formula (1) １ ~R ６ At least three of R are groups represented by formula (2). １ ~R ６ may be a group represented by formula (2), and R １ ~R ６ In view of the fact that the [2+2] cyclization reaction of the cinnamic acid moiety in the compound represented by formula (1) can be more easily carried out, R １ and R ２ and at least one of R ３ and R ４ and at least one of R ５ and R ６ and at least one of the above is preferably a group represented by formula (2).

[0012] R １ ~R ６ The alkyl group represented by the formula (I) may be linear or branched. The number of carbon atoms in the alkyl group may be 1 or more and 16 or less.

[0013] R in formula (2) １１ The alkyl group and alkenyl group represented by the formula (I) may be linear or branched, preferably linear. The number of carbon atoms in the alkyl group and alkenyl group may be 7 or more, 8 or more, or 9 or more, and may be 17 or less, 16 or less, or 15 or less.

[0014] From the viewpoint of improving the strength of the thermally conductive material formed from the composition and improving the intermolecular thermal conductivity due to the increased covalent bond density, R １１ is preferably an alkenyl group, and more preferably a group having a terminal carbon-carbon double bond (vinyl group). １１When p is an alkenyl group, p is preferably 2 from the viewpoint of particularly increasing the thermal conductivity of the thermal conductive material and also increasing the breaking strain.

[0015] The group represented by formula (2) is preferably a group represented by the following formula (2-1): In the formula, p is 1 or 2, and m may each independently be an integer of 5 or more, 6 or more, or 7 or more, or may be an integer of 15 or less, 14 or less, or 13 or less (the same applies to m in the following formulas (2-2) and (2-3)).

[0016] When p in formula (2-1) is 1, the compound represented by formula (2-1) is preferably a group represented by the following formula (2-2).

[0017] When p in formula (2-1) is 2, the compound represented by formula (2-1) is preferably a group represented by the following formula (2-3).

[0018] R １１ When is an alkyl group, the group represented by formula (2) may be a group represented by the following formula (2-4) or (2-5). In the formula, n may be independently an integer of 7 or more, 8 or more, or 9 or more, or may be an integer of 17 or less, 16 or less, or 15 or less.

[0019] The content of the compound represented by formula (1) may be 50% by mass or more, 60% by mass or more, 70% by mass or more, 80% by mass or more, 90% by mass or more, or 95% by mass or more, based on the total amount of the composition.

[0020] The composition may further contain a polymerization initiator, which is preferably a photopolymerization initiator that generates radicals by light.

[0021] The photopolymerization initiator may be, for example, a benzoin ether-based photopolymerization initiator, an acetophenone-based photopolymerization initiator, an α-ketol-based photopolymerization initiator, an aromatic sulfonyl chloride-based photopolymerization initiator, a photoactive oxime-based photopolymerization initiator, a benzoin-based photopolymerization initiator, a benzyl-based photopolymerization initiator, a benzophenone-based photopolymerization initiator, a ketal-based photopolymerization initiator, a thioxanthone-based photopolymerization initiator, or an acylphosphine oxide-based photopolymerization initiator.

[0022] Examples of the benzoin ether photopolymerization initiator include benzoin methyl ether, benzoin ethyl ether, benzoin propyl ether, benzoin isopropyl ether, benzoin isobutyl ether, 2,2-dimethoxy-1,2-diphenylethan-1-one (for example, "Omnirad 651" manufactured by IGM Resins BV), and anisole methyl ether. Examples of the acetophenone-based photopolymerization initiator include 1-hydroxycyclohexyl phenyl ketone (e.g., "Omnirad 184" manufactured by IGM Resins BV), 4-phenoxydichloroacetophenone, 4-t-butyl-dichloroacetophenone, 1-[4-(2-hydroxyethoxy)-phenyl]-2-hydroxy-2-methyl-1-propan-1-one (e.g., "Omnirad 2959" manufactured by IGM Resins BV), 2-hydroxy-2-methyl-1-phenyl-propan-1-one (e.g., "Omnirad 1173" manufactured by IGM Resins BV), methoxyacetophenone, and 2,2-dimethoxy-2-phenylacetophenone.

[0023] Examples of α-ketol photopolymerization initiators include 2-methyl-2-hydroxypropiophenone and 1-[4-(2-hydroxyethyl)-phenyl]-2-hydroxy-2-methylpropan-1-one. Examples of aromatic sulfonyl chloride photopolymerization initiators include 2-naphthalenesulfonyl chloride. Examples of photoactive oxime photopolymerization initiators include 1-phenyl-1,1-propanedione-2-(o-ethoxycarbonyl)-oxime.

[0024] Examples of benzoin-based photopolymerization initiators include benzoin. Examples of benzyl-based photopolymerization initiators include benzil. Examples of benzophenone-based photopolymerization initiators include benzophenone, benzoylbenzoic acid, 3,3'-dimethyl-4-methoxybenzophenone, polyvinyl benzophenone, and α-hydroxycyclohexyl phenyl ketone. Examples of ketal-based photopolymerization initiators include benzil dimethyl ketal. Examples of thioxanthone-based photopolymerization initiators include thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, 2,4-dimethylthioxanthone, isopropylthioxanthone, 2,4-dichlorothioxanthone, 2,4-diethylthioxanthone, isopropylthioxanthone, 2,4-diisopropylthioxanthone, and dodecylthioxanthone.

[0025] Examples of the acylphosphine oxide photopolymerization initiator include bis(2,6-dimethoxybenzoyl)phenylphosphine oxide, bis(2,6-dimethoxybenzoyl)(2,4,4-trimethylpentyl)phosphine oxide, bis(2,6-dimethoxybenzoyl)-n-butylphosphine oxide, bis(2,6-dimethoxybenzoyl)-(2-methylpropan-1-yl)phosphine oxide, bis(2,6-dimethoxybenzoyl)-(1-methylpropan-1-yl)phosphine oxide, and bis(2,6-dimethoxybenzoyl)-n-butylphosphine oxide. benzoyl)-t-butylphosphine oxide, bis(2,6-dimethoxybenzoyl)cyclohexylphosphine oxide, bis(2,6-dimethoxybenzoyl)octylphosphine oxide, bis(2-methoxybenzoyl)(2-methylpropan-1-yl)phosphine oxide, bis(2-methoxybenzoyl)(1-methylpropan-1-yl)phosphine oxide, bis(2,6-diethoxybenzoyl)(2-methylpropan-1-yl)phosphine oxide, bis(2,6-diethoxybenzoyl)(1-methyl bis(2,6-dibutoxybenzoyl)(2-methylpropan-1-yl)phosphine oxide, bis(2,4-dimethoxybenzoyl)(2-methylpropan-1-yl)phosphine oxide, bis(2,4,6-trimethylbenzoyl)(2,4-dipentoxyphenyl)phosphine oxide, bis(2,6-dimethoxybenzoyl)benzylphosphine oxide, bis(2,6-dimethoxybenzoyl)-2-phenylpropylphosphine oxide, bis(2,6-dimethoxy benzoyl)-2-phenylethylphosphine oxide, 2,6-dimethoxybenzoylbenzylbutylphosphine oxide, 2,6-dimethoxybenzoylbenzyloctylphosphine oxide, bis(2,4,6-trimethylbenzoyl)-2,5-diisopropylphenylphosphine oxide, bis(2,4,6-trimethylbenzoyl)-2-methylphenylphosphine oxide, bis(2,4,6-trimethylbenzoyl)-4-methylphenylphosphine oxide, bis(2,4,6-trimethylbenzoyl)-2,5-Diethylphenylphosphine oxide, bis(2,4,6-trimethylbenzoyl)-2,3,5,6-tetramethylphenylphosphine oxide, bis(2,4,6-trimethylbenzoyl)-2,4-di-n-butoxyphenylphosphine oxide, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, bis(2,6-dimethoxybenzoyl)-2,4,4-trimethylpentylphosphine oxide, bis(2,4,6-trimethylbenzoyl)iso butylphosphine oxide, 2,6-dimethythoxybenzoyl-2,4,6-trimethylbenzoyl-n-butylphosphine oxide, bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, bis(2,4,6-trimethylbenzoyl)-2,4-dibutoxyphenylphosphine oxide, 1,10-bis[bis(2,4,6-trimethylbenzoyl)phosphine oxide]decane, tri(2-methylbenzoyl)phosphine oxide, etc.

[0026] The content of the polymerization initiator may be 0.01 parts by mass or more, 0.1 parts by mass or more, or 1 part by mass or more, and may be 10 parts by mass or less, 5 parts by mass or less, or 3 parts by mass or less, relative to 100 parts by mass of the content of the compound represented by Formula (1).

[0027] The composition may further contain a thiol compound from the viewpoint of sufficiently promoting the crosslinking reaction when curing the composition and increasing the strength of the resulting cured product (thermal conductive material). The thiol compound has high activity and can sufficiently promote the crosslinking reaction, particularly when used in combination with the above-mentioned polymerization initiator. The thiol compound may be a monothiol compound having one thiol group or a dithiol compound having two thiol groups, and from the viewpoint of more suitably promoting the crosslinking reaction, it may be a dithiol compound.

[0028] The dithiol compound may be an alkanedithiol. The number of carbon atoms in the alkanedithiol may be 2 or more and 10 or less. Examples of alkanedithiols include 1,2-ethanedithiol, 1,3-propanedithiol, 1,4-butanedithiol, 2,3-butanedithiol, 1,5-pentanedithiol, 1,6-hexanedithiol, 1,8-octanedithiol, and 1,10-decanedithiol.

[0029] The molar ratio of the content of the thiol compound to the content of the polymerization initiator (thiol compound / polymerization initiator) is preferably in the range of 1 or more and 30 or less.

[0030] The composition may further contain an organic solvent. The organic solvent is not particularly limited as long as it can dissolve the compound represented by formula (1), and examples thereof include chloroform, dichloroethane, toluene, acetone, methyl ethyl ketone, methyl isobutyl ketone, ethyl acetate, propyl acetate, and butyl acetate. These organic solvents may be used alone or in combination of two or more.

[0031] The composition may be liquid at 25°C under atmospheric pressure. This allows it to be suitably applied to the surfaces of heat source components, heat dissipation components, etc., and even if the surface to be coated has irregularities, it can be applied so as to smooth out the irregularities. The composition may be solid at 25°C under atmospheric pressure, and in this case, it is preferable that it becomes liquid upon heating (for example, at 50°C or higher).

[0032] The above-mentioned composition is a compound represented by formula (1) in which the carbon-carbon double bonds of the cinnamic acid moieties are subjected to a [2+2] cyclization reaction (R １１ is an alkenyl group, the carbon-carbon double bonds contained in the alkenyl group are also polymerized together. A cured product of the above-mentioned composition has anisotropic thermal conductivity, and is therefore suitable for use as a composition for forming a thermally conductive material (with anisotropic thermal conductivity).

[0033] The article according to this embodiment includes a heat source and a heat conductive material (heat dissipation material) in thermal contact with the heat source. Hereinafter, an electronic component will be described as a more specific example of the article. Fig. 1 is a schematic cross-sectional view showing one embodiment of the electronic component. Fig. 2 is a schematic cross-sectional view showing an enlarged view of a main portion of the electronic component shown in Fig. 1.

[0034] The electronic component 1 shown in FIG. 1 includes a semiconductor component 21 as a heat source, a heat sink 22 as a heat dissipation section, and a thermally conductive material (heat dissipation material) 11 provided between the semiconductor component 21 and the heat sink 22.

[0035] In this electronic component 1, as shown in FIG. 2 , the surfaces of the semiconductor component 21 and the heat sink 22 that contact the thermal conductive material 11 each have a minute unevenness. The thermal conductive material 11 includes a first thermal conductive material 11a and a second thermal conductive material 11b. The first thermal conductive material 11a may be a conventionally known thermal conductive material, for example, a thermal conductive material in which a filler (thermally conductive filler) is dispersed in a resin. The second thermal conductive material (also called a primer) 11b may be a thermal conductive material formed from the above-described thermal conductive material composition. This reduces the thermal resistance between the semiconductor component 21 and the heat sink 22.

[0036] Specifically, if only the first thermally conductive material 11a containing a filler is used as the thermally conductive material, the resin component in the first thermally conductive material 11a will lie flat in-plane, increasing the thermal resistance. Therefore, even if recesses in the surfaces of the semiconductor component 21 and the heat sink 22 are filled, the interfacial thermal resistance between them cannot be sufficiently reduced. In contrast, the thermally conductive material 11 according to this embodiment includes a second thermally conductive material 11b in addition to the first thermally conductive material 11a. This second thermally conductive material 11b is formed using the thermally conductive material composition described above (e.g., a cured product of the thermally conductive material composition). This second thermally conductive material 11b exhibits high thermal conductivity due to molecular alignment in the thickness direction without the use of a filler, allowing efficient heat transfer from the surfaces of the semiconductor component 21 and the heat sink 22 even if the surfaces of the second thermally conductive material 11b are not smooth. Therefore, by including the first thermally conductive material 11a and the second thermally conductive material 11b, the interfacial thermal resistance between the semiconductor component 21 and the heat sink 22 can be reduced.

[0037] In the electronic component 1 described in FIG. 1 , the thermally conductive material 11 is arranged so as to be in direct contact with the semiconductor component 21 and the heat sink 22, but the thermally conductive material 11 only needs to be in thermal contact with the heat source, and in another embodiment, the thermally conductive material 11 may be arranged so as to be in contact with the heat source (semiconductor component) via another member.

[0038] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples.

[0039] Example 1 Synthesis of Compound (1A) A compound represented by the above formula (1), in which R １ ~R ６ is a group represented by the following formula (2a), In formula (2a), m is 7.

[0040] Under a nitrogen atmosphere, 4-(non-9-enyloxy)cinnamic acid (2.6 mmol) was dissolved in dichloromethane (15 mL) and cooled to 0°C. To this was added oxalyl chloride (1.5 mL) and dimethylformamide (0.3 mL), and the mixture was stirred at 35°C for 4 hours. The reaction mixture was concentrated under reduced pressure, and dry tetrahydrofuran (10 mL) was added to the residue to obtain a solution. 2,3,6,7,10,11-hexahydroxytriphenylene (0.089 mmol), 4-dimethylaminopyridine (0.51 mmol), and dry pyridine (2.5 mL) were added to dry tetrahydrofuran (40 mL), and the mixture was cooled to 0°C, after which the above solution was added. The reaction mixture was heated to reflux for 19 hours, allowed to cool, and filtered. The filtrate was concentrated, and the residue was dissolved in chloroform and washed with an aqueous copper sulfate solution. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resulting crude product was purified by silica gel column chromatography to obtain compound (1A) (0.027 mmol).

[0041] (Preparation of Thermally Conductive Material) A solution (thermal conductive material composition) prepared by dissolving compound (1A) (2 mg) in a 1,2-dichloroethane solution (15 μL) containing 1,8-octanedithiol (0.2 M) and 2,2-dimethoxy-2-phenylacetophenone (0.02 M) was dropped onto a glass substrate and air-dried. After being held at 130°C for 1 hour, it was irradiated with ultraviolet light from a high-pressure mercury lamp for 24 hours. Finally, the glass substrate was immersed in hot water to peel off the film (thermal conductive material) used for measuring thermal conductivity.

[0042] (Example 2) (Synthesis of Compound (1B) or (1C)) A compound represented by the above formula (1), in which R in formula (1) is a methyl group, was synthesized by the same procedure as for compound (1A) according to T. Hirose et al., Journal of Polymer Science Part A, 2019, 57, 605-612. １ ~R ６ Compounds (1B) and (1C) in which is a group represented by the following formula (2b) or (2c), respectively, were synthesized. In formula (2b) and formula (2c), n is 10, 12 or 14.

[0043] (Preparation of Thermally Conductive Material) A solution (thermally conductive material composition) prepared by dissolving Compound (1B) or (1C) in chloroform was dropped onto a glass substrate and air-dried. After being kept at 100°C for 1 hour, the substrate was irradiated with ultraviolet light from a high-pressure mercury lamp for 24 hours. Finally, the film was peeled off in water to obtain a film (thermally conductive material) for measuring thermal conductivity.

[0044] (Example 3) (Synthesis of Compound (1D)) A compound represented by the above formula (1), in which R １ ~R ６ is a group represented by the following formula (2d), In formula (2d), m is 7.

[0045] Under a nitrogen atmosphere, 3,4-bis(non-9-enyloxy)cinnamic acid (1.0 mmol) was dissolved in dichloromethane (15 mL) and cooled to 0°C. To this solution, oxalyl chloride (2.0 mL) and dimethylformamide (0.3 mL) were added, and the mixture was stirred at 35°C for 1.5 hours. The reaction mixture was concentrated under reduced pressure, and dry tetrahydrofuran (10 mL) was added to the residue to obtain a solution. 2,3,6,7,10,11-hexahydroxytriphenylene (0.083 mmol), 4-dimethylaminopyridine (0.42 mmol), and dry pyridine (2.5 mL) were added to dry tetrahydrofuran (40 mL), and the mixture was cooled to 0°C, after which the above solution was added. The reaction mixture was heated to reflux for 24 hours, allowed to cool, and filtered. The filtrate was concentrated, and the residue was dissolved in chloroform and washed with an aqueous copper sulfate solution. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resulting crude product was purified by silica gel column chromatography to obtain compound (1D) (0.041 mmol).

[0046] (Preparation of Thermally Conductive Material) A solution (thermal conductive material composition) prepared by dissolving compound (1D) (2 mg) in a 1,2-dichloroethane solution (15 μL) containing 1,8-octanedithiol (0.3 M) and 2,2-dimethoxy-2-phenylacetophenone (0.03 M) was dropped onto a glass substrate and air-dried. After being held at 130°C for 1 hour, it was irradiated with ultraviolet light from a high-pressure mercury lamp for 24 hours. Finally, the glass substrate was immersed in methanol to peel off the film (thermal conductive material) used for measuring thermal conductivity.

[0047] Comparative Example 1 A polyimide film "Kapton 500H / V" (thickness: 125 μm) manufactured by DuPont-Toray Co., Ltd. was used as it was.

[0048] Comparative Example 2 3 g of the mesogenic epoxy resin prepolymer (epoxy equivalent: 329 g / eq) described in Japanese Patent No. 6635201 was used, and an equivalent amount of diaminodiphenyl sulfone was used as a curing agent. The mixture was thermally cured at 170°C for 1 hour, and the cured product was taken out and cut into a film having a thickness of 300 µm.

[0049] (Measurement of Thermal Conductivity) The thermal conductivity of each film in the Examples and Comparative Examples was calculated by measuring the thermal diffusivity in the thickness direction and in-plane direction of the film using an ai-Phase mobile M3 type 1 (thickness direction of the film) and an M10 type 2 (in-plane direction of the film) manufactured by ai-Phase Corporation, which are capable of TWA (temperature wave thermal analysis) measurement based on ISO 22007, and multiplying the result by the density and specific heat. The results are shown in Table 1.

[0050]

[0051] As can be seen from Table 1, the thermal conductive materials of Examples 1 to 3 formed from compositions containing the compound represented by formula (1) exhibited anisotropic thermal conductivity. The thermal conductive materials of Examples 1 to 3 exhibited higher thermal conductivity in the thickness direction as well as in the in-plane direction compared to the thermal conductive materials of Comparative Examples 1 and 2. Furthermore, the thermal conductive material of Example 1 was superior in strength compared to the thermal conductive material of Example 2, and maintained its shape even when the film was peeled off.

[0052] (Measurement of Breaking Strain and Tensile Modulus of Elasticity) The breaking strain and tensile modulus of elasticity of the thermal conductive materials of Examples 1 and 3 were measured at 25°C using a tensile tester ("Autograph EZ-TEST EZ-S" manufactured by Shimadzu Corporation). The results are shown in Table 2. In the measurement, the thermal conductive material having a shape of 0.05 mm (thickness) x 5 mm (width) x 25 mm (length) was measured in accordance with JIS K7161 under the conditions of a chuck distance of 20 mm and a tensile speed of 5 mm / min. The tensile modulus of elasticity Et was calculated based on the values ​​of strain at two specified points using the following formula: Et=(σ ２ -σ １ ) / (ε ２ -ε １ ) Et: tensile modulus (MPa) σ １ : strain ε １ Stress (MPa) at = 0.0005 (0.05%) σ ２ : strain ε ２ = Stress (MPa) at 0.0025 (0.25%)

[0053]

[0054] 1...electronic component, 11...thermal conductive material, 11a...first thermal conductive material, 11b...second thermal conductive material (primer), 21...semiconductor component, 22...heat sink

Claims

1. A composition for a thermal conductive material comprising a compound represented by the following formula (1): [In the formula, R １ ~R ６ are each independently a group represented by the following formula (2) or an alkyl group, R １ ~R ６ At least three of the above are groups represented by formula (2). In the formula, R １１ is an alkyl group or an alkenyl group, and p is 1 or 2.

2. The composition for thermal conductive materials according to claim 1, wherein the group represented by formula (2) is a group represented by the following formula (2-1): [In the formula, p is 1 or 2, and each m independently represents an integer of 5 to 15.] 3. The composition for thermal conductive materials according to claim 1, wherein the group represented by the formula (2) is a group represented by the following formula (2-3): [In the formula, each m independently represents an integer of 5 to 15.] 4. The composition for thermal conductive materials according to any one of claims 1 to 3, further comprising a polymerization initiator.

5. A thermally conductive material formed from the thermally conductive material composition according to claim 4.

6. An article comprising: a heat source; and the thermally conductive material of claim 5 in thermal contact with said heat source.

7. An electronic component comprising: a semiconductor component; a heat sink; and a thermally conductive material provided between the semiconductor component and the heat sink, the thermally conductive material including the thermally conductive material according to claim 5.

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