Thermally conductive material composition, thermally conductive material, article, and electronic component

Abstract

A composition for use in a thermally conductive material, comprising a compound represented by the following formula (1), wherein R 1 ~R 6 R is independently represented by the group or alkyl group of formula (2) below. 1 ~R 6 At least three of them are groups represented by formula (2). In formula (2), R 11 It is alkyl or alkenyl, and p is 1 or 2.

Description

Technical Field

[0001] This invention relates to a composition for thermally conductive materials, thermally conductive materials, articles, and electronic components. Background Technology

[0002] In electronic components such as processors and power modules, heat is generated during their operation. To protect these components from the effects of heat, methods are needed to effectively dissipate the generated heat. Thermally conductive materials, known as thermal interface materials (TIMs), are placed between heat sources and heat sinks to reduce the thermal resistance between them and promote heat conduction from the heat source.

[0003] In recent years, organic thermally conductive materials that do not use inorganic fillers have been studied as thermally conductive membranes (TIMs) for thin-film structures. Specifically, for example, as disclosed in Non-Patent Documents 1 and 2, discoid liquid crystal polymer films are known to exhibit high in-plane thermal conductivity. In such discoid liquid crystal polymer films, molecules are oriented in a specific direction using a magnetic field or similar means. This is intended for use as a heat spreader, where the heat spreader exhibits a particularly high thermal conductivity (anisotropic thermal conductivity) in the in-plane direction of the film, allowing heat to diffuse inwards. However, since the thermal conductivity in the thickness direction is extremely low and it functions as an insulating material, its heat transfer performance as a heat sink for dissipating heat from a heat source to the outside cannot be expected.

[0004] Previous technical documents Patent documents Non-patent document 1: "Highly anisotropic thermalconductivity of discoticnematic liquid crystalline films with homeotropic alignment", Dong-Gyun Kim, Yun Ho Kim, Tae Joo Shin, Eun Jung Cha, Da SomKim, Byoung Gak Kim, YoungjaeYoo, Yong Seok Kim, Mi Hye Yi and Jong ChanWonab, Chem. Commun., 2017, 53,8227-8230 Non-patent document 2: "Heat Transfer OrganicMaterials: Robust Polymer Filmswith the Outstanding Thermal ConductivityFabricated by thePhotopolymerization of Uniaxially Oriented Reactive Discogens", Dong-Gue Kang, Minwook Park, Dae-Yoon Kim, Munju Goh, Namil Kim and Kwang-UnJeong, ACSAppl.Mater. Interfaces 2016, 8, 30492-30501 Summary of the Invention

[0005] The technical problem to be solved by the invention One objective of this invention is to provide a composition capable of forming a novel thermally conductive material with anisotropic thermal conductivity.

[0006] means for solving technical problems The inventors have discovered that by introducing cinnamic acid sites into the triphenylene skeleton, which serves as the core, the carbon-carbon double bonds contained in the cinnamic acid sites react with each other and cyclize, and the molecules are immobilized near the core, thus exhibiting anisotropic thermal conductivity based on the high order of the columnar structure.

[0007] The present invention includes the following aspects.

[0008] [1] A composition for thermally conductive materials, comprising a compound represented by the following formula (1).

[0009] In the formula, R 1 ~R 6 R is independently represented by the group or alkyl group of formula (2) below. 1 ~R 6 At least three of them are groups represented by the following formula (2).

[0010] In the formula, R 11 It is alkyl or alkenyl, and p is 1 or 2.

[0011] [2] The composition for thermally conductive materials according to [1], wherein, The group represented by formula (2) is the same group represented by formula (2-1) below.

[0012] In the formula, p is 1 or 2, and m independently represents integers greater than 5 and less than 15.

[0013] [3] The composition for thermally conductive materials according to [1], wherein, The group represented by formula (2) is the same group represented by formula (2-3) below.

[0014] In the formula, m independently represents integers greater than 5 and less than 15.

[0015] [4] The composition for thermally conductive materials according to any one of [1] to [3] further contains a polymerization initiator.

[0016] [5] A thermally conductive material formed from any one of the thermally conductive materials described in [1] to [3] using a composition.

[0017] [6] An article having a heat source and a thermally conductive material described in [5] in thermal contact with the heat source.

[0018] [7] An electronic component comprising a semiconductor component, a heat sink and a thermally conductive material disposed between the semiconductor component and the heat sink, the thermally conductive material comprising the thermally conductive material described in [5].

[0019] Invention Effects 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. Furthermore, according to another aspect of the present invention, for example, when forming a film-like thermally conductive material, a high thermal conductivity can be obtained in the thickness direction of the film, and also in the in-plane direction (the direction perpendicular to the thickness direction) of the film. Furthermore, according to another aspect of the present invention, by utilizing the [2+2] cyclization reaction of the cinnamic acid site in the compound represented by formula (1), an appropriate crosslinking density can be achieved in the thermally conductive material. Furthermore, according to another aspect of the present invention, a liquid crystal phase can be formed from a single component of the compound represented by formula (1), thus making it easy to predict and maintain the liquid crystal phase. Attached Figure Description

[0020] Figure 1 This is a schematic cross-sectional view showing one embodiment of the article.

[0021] Figure 2 It is Figure 1 A schematic cross-sectional view showing the enlarged portion of the object shown. Detailed Implementation

[0022] The thermally conductive material composition (hereinafter also referred to as "the composition") according to one embodiment of the present invention contains a compound represented by the following formula (1).

[0023] In the formula, R 1 ~R 6 Each is independently represented by a group or alkyl group as shown in formula (2) below.

[0024] In the formula, R 11 It is alkyl or alkenyl, and p is 1 or 2.

[0025] In equation (1), R 1 ~R 6 At least three of them are groups represented by formula (2). They can be R 1 ~R 6 The three, four, or five groups in the formula (2) can also be R. 1 ~R 6 All groups are represented by formula (2). From the viewpoint that the [2+2] cyclization reaction of the cinnamic acid site in the compound represented by formula (1) is more likely to proceed, the number of carbon atoms R is preferred. 1 and R 2 At least one of them, R 3 and R 4 At least one of them, and R 5 and R 6 At least one of them is a group represented by formula (2).

[0026] R 1 ~R 6 The alkyl group can be straight-chain or branched. The alkyl group can have more than one carbon atom and less than 16 carbon atoms.

[0027] R in equation (2) 11 The alkyl and alkenyl groups represented can be linear or branched, preferably linear. The number of carbon atoms in the alkyl and alkenyl groups can be 7 or more, 8 or more, or 9 or more, and can be 17 or less, 16 or less, or 15 or less.

[0028] From the viewpoint that it can improve the strength of the thermally conductive material formed from the composition and can increase the intermolecular thermal conductivity through the increase of covalent bond density, R 11 Preferably, it is an alkenyl group, more preferably a group having a carbon-carbon double bond (vinyl) at the end. R 11 When the form is alkenyl, from the viewpoint that it can particularly improve the thermal conductivity of the thermally conductive material and also improve the fracture strain, p is preferably 2.

[0029] The group represented by formula (2) is preferably the group represented by formula (2-1) below.

[0030] In the formula, p is 1 or 2, and m can be an integer of 5 or more, 6 or more, or 7 or more, and can be an integer of 15 or less, 14 or less, or 13 or less (m in the following formulas (2-2) and (2-3) also has the same meaning).

[0031] When p is 1 in formula (2-1), the compound represented by formula (2-1) is preferably represented by the group represented by the following formula (2-2).

[0032] When p is 2 in formula (2-1), the compound represented by formula (2-1) is preferably represented by the group represented by the following formula (2-3).

[0033] R 11 When it is an alkyl group, the group represented by formula (2) can be the group represented by formula (2-4) or (2-5) below.

[0034] In the formula, n can be an integer greater than or equal to 7, greater than or equal to 8, or greater than or equal to 9, and can be an integer less than or equal to 17, less than or equal to 16, or less than or equal to 15.

[0035] The content of the compound represented by formula (1) is based on the total amount of the composition and can be 50% or more by mass, 60% or more by mass, 70% or more by mass, 80% or more by mass, 90% or more by mass, or 95% or more by mass.

[0036] The composition may further contain a polymerization initiator. The polymerization initiator is preferably a photopolymerization initiator that generates free radicals through light.

[0037] Photopolymerization initiators can be, for example, benzoin ether photopolymerization initiators, acetophenone photopolymerization initiators, α-keto alcohol photopolymerization initiators, aromatic sulfonyl chloride photopolymerization initiators, photoactive oxime photopolymerization initiators, benzoin photopolymerization initiators, benzyl photopolymerization initiators, benzophenone photopolymerization initiators, ketal photopolymerization initiators, thioxanone photopolymerization initiators, acylphosphine oxide photopolymerization initiators, etc.

[0038] Examples of benzoin ether photopolymerization initiators include benzoin methyl ether, benzoin ethyl ether, benzoin propyl ether, benzoin isopropyl ether, benzoin isobutyl ether, 2,2-dimethoxy-1,2-diphenylethane-1-one (e.g., "Omnirad 651" manufactured by IGM Resins BV), and anisole methyl ether. Examples of acetophenone-based photopolymerization initiators include 1-hydroxycyclohexylphenyl ketone (e.g., "Omnirad 184" manufactured by IGM Resins BV), 4-phenoxydichloroacetophenone, 4-tert-butyl-dichloroacetophenone, 1-[4-(2-hydroxyethoxy)-phenyl]-2-hydroxy-2-methyl-1-propane-1-one (e.g., "Omnirad 2959" manufactured by IGM Resins BV), 2-hydroxy-2-methyl-1-phenyl-propane-1-one (e.g., "Omnirad 1173" manufactured by IGM Resins BV), methoxyacetophenone, and 2,2-dimethoxy-2-phenylacetophenone.

[0039] Examples of α-ketool photopolymerization initiators include 2-methyl-2-hydroxypropanone and 1-[4-(2-hydroxyethyl)-phenyl]-2-hydroxy-2-methylpropane-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.

[0040] Examples of benzoin-based photopolymerization initiators include benzoin, etc. Examples of benzyl-based photopolymerization initiators include benzyl, etc. Examples of benzophenone-based photopolymerization initiators include benzophenone, benzoylbenzoic acid, 3,3'-dimethyl-4-methoxybenzophenone, polyvinylbenzophenone, α-hydroxycyclohexylphenyl ketone, etc. Examples of acetal-based photopolymerization initiators include benzyl dimethyl acetal, etc. 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, dodecylthioxanthone, etc.

[0041] Examples of acylphosphine oxide photopolymerization initiators 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-methylpropane-1-yl)phosphine oxide, bis(2,6-dimethoxybenzoyl)-(1-methylpropane-1-yl)phosphine oxide, bis(2,6-dimethoxybenzoyl)-tert-butylphosphine oxide, bis(2,6-dimethoxybenzoyl)cyclohexylphosphine oxide, bis(2,6-dimethoxybenzoyl)octylphosphine oxide, and bis(2-methoxybenzoyl)cyclohexylphosphine oxide. Bis(2-methoxybenzoyl)(1-methylpropane-1-yl)phosphine oxide, Bis(2,6-diethoxybenzoyl)(2-methylpropane-1-yl)phosphine oxide, Bis(2,6-diethoxybenzoyl)(1-methylpropane-1-yl)phosphine oxide, Bis(2,6-dibutoxybenzoyl)(2-methylpropane-1-yl)phosphine oxide, Bis(2,4-dimethoxybenzoyl)(2-methylpropane-1-yl)phosphine oxide, Bis(2,4,6-trimethylbenzoyl)(2,4-dipentoxyphenyl)phosphine oxide, Bis(2,6-dimethoxybenzoyl)benzyl ... bis(2,6-dimethoxybenzoyl)-2-phenylpropylphosphine oxide, bis(2,6-dimethoxybenzoyl)-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... Phosphorus oxides include (6-trimethylbenzoyl)-2,4-di-n-butoxyphenylphosphine oxide, 2,4,6-trimethylbenzoyl diphenylphosphine oxide, bis(2,6-dimethoxybenzoyl)-2,4,4-trimethylpentylphosphine oxide, bis(2,4,6-trimethylbenzoyl)isobutylphosphine oxide, 2,6-dimethoxybenzoyl-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, and tris(2-methylbenzoyl)phosphine oxide.

[0042] The content of the polymerization initiator relative to the content of the compound represented by formula (1) in 100 parts by mass can be more than 0.01 parts by mass, more than 0.1 parts by mass, or more than 1 part by mass, and can be less than 10 parts by mass, less than 5 parts by mass, or less than 3 parts by mass.

[0043] From the viewpoint of ensuring sufficient cross-linking reaction during curing of the composition and improving the strength of the resulting cured material (thermal conductive material), the composition may further contain a thiol compound. Thiol compounds are highly reactive, especially when used in conjunction with the aforementioned polymerization initiator, enabling sufficient cross-linking reaction. The thiol compound can be a monothiol compound having one thiol group or a dithiol compound having two thiol groups; from the viewpoint of more suitable cross-linking reaction, a dithiol compound is preferred.

[0044] Dithiol compounds can be alkane dithiols. The number of carbon atoms in alkane dithiols can be more than 2 or less than 10. Examples of alkane dithiols 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.

[0045] The molar ratio of the content of thiol compound to the content of polymerization initiator (thiol compound / polymerization initiator) is preferably in the range of 1 or more and 30 or less.

[0046] The composition may further contain an organic solvent. There are no particular limitations on the organic solvent, as long as it can dissolve the compound represented by formula (1), and examples include chloroform, dichloroethane, toluene, acetone, methyl ethyl ketone, methyl isobutyl ketone, ethyl acetate, propyl acetate, butyl acetate, etc. These organic solvents may be used alone or in combination of two or more.

[0047] The composition can be in a liquid state at atmospheric pressure and 25°C. Therefore, it can be suitably coated onto the surface of parts that serve as heat sources, heat dissipation parts, etc., and can smooth out any unevenness on the coating surface. The composition can also be in a solid state at atmospheric pressure and 25°C; in this case, it is preferable to make it liquid by heating (e.g., above 50°C).

[0048] The above composition is formed by the [2+2] cyclization reaction of the carbon-carbon double bonds at the cinnamic acid site in the compound represented by formula (1) (R in formula (2)). 11When the alkenyl group is used, the carbon-carbon double bonds contained in the alkenyl group are polymerized together to form a curable composition. Since the cured product of the above composition has anisotropic thermal conductivity, it is suitable as a composition for forming anisotropic thermally conductive materials.

[0049] The article described in this embodiment includes a heat source and a thermally conductive material (heat dissipation material) that comes into thermal contact with the heat source. Hereinafter, as a more specific example of this article, an electronic component will be used for illustration. Figure 1 This is a schematic cross-sectional view showing one embodiment of an electronic component. Figure 2 It is Figure 1 An enlarged schematic cross-sectional view of the main part of the electronic component shown.

[0050] Figure 1 The electronic component 1 shown includes a semiconductor component 21 as a heat source, a heat sink 22 as a heat dissipation part, and a thermally conductive material (heat dissipation material) 11 disposed between the semiconductor component 21 and the heat sink 22.

[0051] In this electronic component 1, such as Figure 2 As shown, the surfaces of the semiconductor component 21 and the heat sink 22 that contact the thermally conductive material 11 each have minute irregularities. The thermally conductive material 11 comprises a first thermally conductive material 11a and a second thermally conductive material 11b. The first thermally conductive material 11a can be a conventionally known thermally conductive material, such as a thermally conductive material in which filler (thermally conductive filler) is dispersed in a resin. The second thermally conductive material (also called a primer) 11b can be a thermally conductive material formed from a composition of the aforementioned thermally conductive materials. This reduces the thermal resistance between the semiconductor component 21 and the heat sink 22.

[0052] Specifically, if only a first thermally conductive material 11a containing filler is used as the thermally conductive material, the resin component in the first thermally conductive material 11a becomes laterally distributed in the plane, resulting in increased thermal resistance. Therefore, even if the recesses on 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 aforementioned thermally conductive material composition (for example, a cured product of the thermally conductive material composition). Even without the use of filler, it can achieve high thermal conductivity due to molecular alignment in the thickness direction. Therefore, even if the surface of the second thermally conductive material 11b is not smooth, heat can be effectively transferred from the surfaces of the semiconductor component 21 and the heat sink 22. Therefore, by including both 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.

[0053] Figure 1In the electronic component 1 described herein, the thermally conductive material 11 is configured to be in direct contact with the semiconductor component 21 and the heat sink 22. However, the thermally conductive material 11 only needs to be in thermal contact with the heat source. In another embodiment, it can be configured to be in contact with the heat source (semiconductor component) via other components.

[0054] Example The present invention will now be described in more detail with reference to embodiments. However, the present invention is not limited to these embodiments.

[0055] (Example 1) (Synthesis of compound (1A)) Following the steps above, R, represented by equation (1) and defined in equation (1), was synthesized. 1 ~R 6 Compound (1A) is a group represented by the following formula (2a).

[0056] In equation (2a), m is 7.

[0057] Under a nitrogen atmosphere, 2.6 mmol of 4-(non-9-enoxy)cinnamic acid was dissolved in 15 mL of dichloromethane and cooled to 0 °C. Oxalyl chloride (1.5 mL) and dimethylformamide (0.3 mL) were added, and the mixture was stirred at 35 °C for 4 hours. The reaction solution was concentrated under reduced pressure, and 10 mL of dry tetrahydrofuran was added to the residue to obtain a solution. 0.089 mmol of 2,3,6,7,10,11-hexahydroxytriphenylene, 0.51 mmol of 4-dimethylaminopyridine, and 2.5 mL of dry pyridine were added to 40 mL of dry tetrahydrofuran, and the mixture was cooled to 0 °C before adding the above solution. The reaction solution was refluxed for 19 hours, allowed to cool naturally, and filtered. The filtrate was concentrated, the residue was dissolved in chloroform, and washed with an aqueous solution of copper sulfate. The organic layer was dried with anhydrous sodium sulfate and then concentrated under reduced pressure. The crude product was purified using silica gel column chromatography to obtain compound (1A) (0.027 mmol).

[0058] (The fabrication of thermally conductive materials) The solution (composition for thermal conductive material) obtained by dissolving compound (1A) (2 mg) in 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 kept at 130°C for 1 hour, it was irradiated with ultraviolet light using 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.

[0059] (Example 2) (Synthesis of compound (1B) or (1C)) Following the same steps as compound (1A), compounds represented by formula (1) and R in formula (1) were synthesized. 1 ~R 6 Compounds (1B) or (1C) that have groups represented by formulas (2b) or (2c) below.

[0060] In equations (2b) and (2c), n is 10, 12, or 14.

[0061] (The fabrication of thermally conductive materials) A solution (composition for thermally conductive materials) obtained 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, it was irradiated with ultraviolet light using 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.

[0062] (Example 3) (Synthesis of compound (1D)) The following steps were used to synthesize R, which is represented by the above equation (1) and contains R in equation (1). 1 ~R 6 Compound (1D) is a group represented by the following formula (2d).

[0063] In equation (2d), m is 7.

[0064] Under a nitrogen atmosphere, 1.0 mmol of 3,4-bis(nonyl-9-enoxy)cinnamic acid was dissolved in 15 mL of dichloromethane and cooled to 0 °C. Oxygenyl chloride (2.0 mL) and dimethylformamide (0.3 mL) were added, and the mixture was stirred at 35 °C for 1.5 h. The reaction solution was concentrated under reduced pressure, and 10 mL of dry tetrahydrofuran was added to the residue to obtain a solution. 0.083 mmol of 2,3,6,7,10,11-hexahydroxytriphenylene (0.083 mmol), 0.42 mmol of 4-dimethylaminopyridine, and 2.5 mL of dry pyridine were added to 40 mL of dry tetrahydrofuran, and the mixture was cooled to 0 °C before adding the above solution. The reaction solution was heated under reflux for 24 h, allowed to cool naturally, and then filtered. The filtrate was concentrated, the residue was dissolved in chloroform, and washed with an aqueous solution of copper sulfate. The organic layer was dried with anhydrous sodium sulfate and then concentrated under reduced pressure. The crude product was purified using silica gel column chromatography to obtain compound (1D) (0.041 mmol).

[0065] (The fabrication of thermally conductive materials) The solution (composition for thermal conductive material) obtained by dissolving compound (1D) (2 mg) in 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 kept at 130°C for 1 hour, it was irradiated with ultraviolet light using 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.

[0066] (Comparative Example 1) The polyimide film "Kapton 500H / V" (125μm thick) manufactured directly by TORAY DUPONT KK is used.

[0067] (Comparative Example 2) Using 3g of the mesocrystalline epoxy resin prepolymer (epoxy equivalent 329g / eq) described in Patent No. 6635201, and using diaminodiphenyl sulfone as the curing agent equivalent, the mixture was heat-cured at 170°C for 1 hour. The cured product was then removed and cut into a film with a thickness of 300μm for use.

[0068] (Determination of thermal conductivity) The thermal conductivity of each membrane in the examples and comparative examples was calculated as follows: using ai-phase Co.'s ai-Phase mobile M3 type1 (thickness direction) and M10 type2 (in-plane direction) membranes, which can be measured using the TWA (Temperature Wave Thermal Analysis) method based on ISO22007, the thermal diffusivity in the thickness direction and in-plane direction of the membrane was measured, and then multiplied by the density and specific heat for calculation. The results are shown in Table 1.

[0069] [Table 1]

[0070] As shown in Table 1, the thermally conductive materials of Examples 1-3, formed from compositions containing the compound represented by formula (1), exhibit anisotropic thermal conductivity. Compared to the thermally conductive materials of Comparative Examples 1 and 2, the thermally conductive materials of Examples 1-3 exhibit high thermal conductivity in the thickness direction and also high thermal conductivity in the in-plane direction. Furthermore, the thermally conductive material of Example 1 also exhibits superior strength compared to the thermally conductive material of Example 2, maintaining its shape even after the film is peeled off.

[0071] (Determination of fracture strain and tensile modulus of elasticity) For the thermally conductive materials of Examples 1 and 3, the fracture strain and tensile modulus at 25°C were measured using a tensile testing machine (Autograph EZ-TEST EZ-S manufactured by Shimadzu Corporation). The results are shown in Table 2. During the measurement, for thermally conductive materials with a shape of 0.05 mm (thickness) × 5 mm (width) × 25 mm (length), the measurements were performed according to JIS K7161, with a clamping distance of 20 mm and a tensile speed of 5 mm / min. The tensile modulus Et was calculated from the specified strain values ​​at two points using the following formula: Et=(σ2-σ1) / (ε2-ε1) Et: Tensile modulus of elasticity (MPa) σ1: Stress (MPa) at strain ε1 = 0.0005 (0.05%) σ2: Stress (MPa) at strain ε2 = 0.0025 (0.25%) [Table 2]

[0072] [Symbol Explanation] 1-Electronic components, 11-Thermal conductive materials, 11a-First thermal conductive material, 11b-Second thermal conductive material (undercoat), 21-Semiconductor components, 22-Heat sink.

Claims

1. A composition for use as a thermally conductive material, comprising a compound represented by the following formula (1), In the formula, R 1 ~R 6 R is independently represented by the group or alkyl group of formula (2) below. 1 ~R 6 At least three of them are groups represented by the formula (2). In the formula, R 11 It is alkyl or alkenyl, and p is 1 or 2.

2. The composition for thermally conductive materials according to claim 1, wherein, The group represented by formula (2) is the group represented by formula (2-1) below. In the formula, p is 1 or 2, and m independently represents integers greater than 5 and less than 15.

3. The composition for thermally conductive materials according to claim 1, wherein, The group represented by formula (2) is the group represented by formula (2-3) below. In the formula, m independently represents integers greater than 5 and less than 15.

4. The composition for thermally conductive materials according to any one of claims 1 to 3, further comprising a polymerization initiator.

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

6. An item that possesses: Heat source; and The thermally conductive material of claim 5 is in thermal contact with the heat source.

7. An electronic component comprising: Semiconductor components; Heat sink; and A thermally conductive material is disposed between the semiconductor component and the heat sink. The thermally conductive material comprises the thermally conductive material according to claim 5.

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