Curable composition, thermally conductive material, thermally conductive sheet, device with thermally conductive layer, compound

Abstract

To provide a curable composition capable of forming a thermally conductive material having excellent thermal conductivity and excellent peel strength from an adherend.SOLUTION: The curable composition contains a curable compound and inorganic particles. The inorganic particles are selected from the group consisting of inorganic nitride particles and inorganic oxide particles. The curable composition satisfies the following requirement 1 or 2. Requirement 1: the inorganic particles are surface-modified with at least one selected from the group consisting of a compound having a polymer chain and two or more alkoxysilyl groups, a hydrolysate of the compound, and a hydrolysis condensate of the compound. Requirement 2: the curable composition contains at least one selected from the group consisting of the compound, a hydrolysate of the compound, and a hydrolysis condensate of the compound.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a curable composition, a thermally conductive material, a thermally conductive sheet, a device with a thermally conductive layer, and a compound. [Background technology]

[0002] Power semiconductor devices used in various electrical equipment such as personal computers, general home appliances, and automobiles have been rapidly becoming smaller in size in recent years. As the size of these devices decreases, it has become more difficult to control the heat generated by these highly dense power semiconductor devices. To address this issue, thermally conductive materials are used to promote heat dissipation from power semiconductor devices. For example, Patent Document 1 discloses a method for producing a heat-dissipating sheet (thermally conductive sheet), and also discloses a method for treating inorganic filler (inorganic particles) contained in the heat-dissipating sheet with a silane coupling agent. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] International Publication No. 2019 / 117156 Summary of the Invention [Problem to be solved by the invention]

[0004] A thermally conductive material formed using a curable composition is required to have high thermal conductivity. Furthermore, the thermally conductive material formed using the curable composition is also required to have excellent peel strength when adhered to an object (also called an "adherend", for example, metal).

[0005] The present inventors have studied the curable composition described in Patent Document 1 and have found that it is difficult to achieve both thermal conductivity and peel strength in the thermal conductive material formed using the curable composition using the silane coupling agent described in Patent Document 1.

[0006] Therefore, an object of the present invention is to provide a curable composition that can form a thermally conductive material that has excellent thermal conductivity and excellent peel strength with respect to an adherend. Another object of the present invention is to provide a thermally conductive material, a thermally conductive sheet, a device with a thermally conductive layer, and a compound related to the curable composition. [Means for solving the problem]

[0007] The present inventors have conducted extensive research to solve the above problems and have completed the present invention. That is, they have found that the above problems can be solved by the following configuration.

[0008] [1] A curable composition comprising a curable compound and inorganic particles, the inorganic particles are selected from the group consisting of inorganic nitride particles and inorganic oxide particles; A curable composition that satisfies the following requirement 1 or requirement 2: Requirement 1: The inorganic particles are surface-modified with at least one selected from the group consisting of a compound having a polymer chain and two or more alkoxysilyl groups, a hydrolyzate of the compound, and a hydrolyzed condensate of the compound. Requirement 2: The curable composition contains at least one selected from the group consisting of the compound, a hydrolyzate of the compound, and a hydrolysis condensate of the compound. [2] The curable composition according to [1], wherein the compound is a compound represented by formula (a) described below. [3] m in the formula (a) described below a The curable composition according to [2], wherein is 3 or 4. [4] The curable composition according to any one of [1] to [3], wherein the polymer chain has a repeating unit represented by formula (y) described below. [5] The curable composition according to any one of [1] to [4], wherein the polymer chain has a repeating unit having an acid anhydride group or a repeating unit having an aromatic heterocyclic group. [6] The curable composition according to any one of [1] to [5], wherein the polymer chain has a polymerizable group selected from the group consisting of an acryloyl group, a methacryloyl group, an oxiranyl group, and a vinyl group. [7] The curable composition according to any one of [1] to [6], wherein the inorganic particles are boron nitride particles or aggregates thereof. [8] The curable composition according to any one of [1] to [7], wherein the inorganic particles are aggregates of boron nitride particles. [9] The curable composition according to any one of [1] to [8], further comprising an epoxy compound.

[10] The curable composition according to any one of [1] to [9], further comprising a phenol compound.

[11] The curable composition contains an epoxy compound and a phenol compound, The curable composition according to any one of [1] to

[10] , wherein the phenol compound has 3 to 7 hydroxyl groups in the molecule.

[12] The curable composition contains an epoxy compound and a phenol compound, The curable composition according to any one of [1] to

[11] , which satisfies at least one of the requirements that the epoxy compound has a triazine skeleton and that the phenol compound has a triazine skeleton.

[13] The curable composition according to any one of [1] to

[12] , further comprising a curing accelerator.

[14] The curable composition according to

[13] , wherein the curing accelerator contains a phosphorus atom.

[15] A thermally conductive material formed by curing the curable composition according to any one of [1] to

[14] .

[16] A thermally conductive sheet made of the thermally conductive material according to

[15] .

[17] A device with a thermally conductive layer, comprising: a device; and a thermally conductive layer including the thermally conductive sheet according to

[16] , arranged so as to be in contact with the device.

[18] A compound represented by the formula (a) described below. [Effects of the Invention]

[0009] According to the present invention, it is possible to provide a curable composition that can form a thermally conductive material that has excellent thermal conductivity and excellent peel strength with respect to an adherend. The present invention also provides a thermally conductive material, a thermally conductive sheet, a device with a thermally conductive layer, and a compound related to the curable composition. DETAILED DESCRIPTION OF THE INVENTION

[0010] The present invention will be described in detail below. The following description of the components may be based on a representative embodiment of the present invention, but the present invention is not limited to such an embodiment.

[0011] The following describes the meaning of each description in this specification. In this specification, a numerical range expressed using "to" means a range that includes the numerical values ​​before and after "to" as the lower and upper limits.

[0012] In this specification, the number average molecular weight and weight average molecular weight are determined by gel permeation chromatography (GPC) in terms of polystyrene.

[0013] In this specification, "solid content" refers to the components that form the thermally conductive material and does not include solvents. The components that form the thermally conductive material may be components that undergo a reaction (polymerization) and change their chemical structure when forming the thermally conductive material. Furthermore, any component that forms the thermally conductive material is considered to be a solid content even if it is in a liquid state.

[0014] In this specification, "(meth)acrylamide" means "either one or both of acrylamide and methacrylamide." "(meth)acrylic" means "either one or both of acrylic and methacrylic."

[0015] In this specification, the acid anhydride group may be either a monovalent group or a divalent group. When the acid anhydride group is a monovalent group, examples thereof include substituents formed by removing any hydrogen atom from acid anhydrides such as maleic anhydride, phthalic anhydride, pyromellitic anhydride, and trimellitic anhydride. When the acid anhydride group is a divalent group, it means a group represented by *-CO-O-CO-* (* indicates the bonding position).

[0016] In this specification, a substituent or the like that is not specified as substituted or unsubstituted may, if possible, further have a substituent (e.g., a group of substituents Y described below) within a range that does not impair the intended effect. For example, the expression "alkyl group" means a substituted or unsubstituted alkyl group (an alkyl group that may have a substituent) within a range that does not impair the intended effect. In addition, in the present specification, when it is stated that "may have a substituent," the type, position, and number of the substituent are not particularly limited. The number of the substituents may be, for example, one or two or more. Examples of the substituent include monovalent non-metallic atomic groups excluding hydrogen atoms, and groups selected from the following substituent group Y are preferred. In this specification, examples of halogen atoms include chlorine atoms, fluorine atoms, bromine atoms, and iodine atoms.

[0017] Substituent group Y: Halogen atoms (-F, -Br, -Cl, -I, etc.), hydroxy groups, amino groups, carboxylic acid groups and their conjugate base groups, carboxylic anhydride groups, cyanate ester groups, unsaturated polymerizable groups, epoxy groups, oxetanyl groups, aziridinyl groups, thiol groups, isocyanate groups, thioisocyanate groups, aldehyde groups, alkoxy groups, aryloxy groups, alkylthio groups, arylthio groups, alkyldithio groups, aryldithio groups, N-alkylamino groups, N,N-dialkylamino groups, N-arylamino groups, N,N-diarylamino groups, N-alkyl-N-arylamino groups group, acyloxy group, carbamoyloxy group, N-alkylcarbamoyloxy group, N-arylcarbamoyloxy group, N,N-dialkylcarbamoyloxy group, N,N-diarylcarbamoyloxy group, N-alkyl-N-arylcarbamoyloxy group, alkylsulfoxy group, arylsulfoxy group, acylthio group, acylamino group, N-alkylacylamino group, N-arylacylamino group, ureido group, N'-alkylureido group, N',N'-dialkylureido group, N'-arylureido group, N',N'-diarylureido group , N'-alkyl-N'-arylureido group, N-alkylureido group, N-arylureido group, N'-alkyl-N-alkylureido group, N'-alkyl-N-arylureido group, N',N'-dialkyl-N-alkylureido group, N',N'-dialkyl-N-arylureido group, N'-aryl-N-alkylureido group, N'-aryl-N-arylureido group, N',N'-diaryl-N-alkylureido group, N',N'-diaryl-N-arylureido group, N'-alkyl-N'-aryl-N-alkylureido group , N'-alkyl-N'-aryl-N-arylureido group, alkoxycarbonylamino group, aryloxycarbonylamino group, N-alkyl-N-alkoxycarbonylamino group, N-alkyl-N-aryloxycarbonylamino group, N-aryl-N-alkoxycarbonylamino group, N-aryl-N-aryloxycarbonylamino group, formyl group, acyl group, alkoxycarbonyl group, aryloxycarbonyl group, carbamoyl group, N-alkylcarbamoyl group, N,N-dialkylcarbamoyl group, N-arylcarbamoyl group, N,N-diarylcarbamoyl group, N-alkyl-N-arylcarbamoyl group, alkylsulfinyl group, arylsulfinyl group, alkylsulfonyl group, arylsulfonyl group, sulfo group (-SO3H) and its conjugate base group, alkoxysulfonyl group, aryloxysulfonyl group, sulfinamoyl group, N-alkylsulfinamoyl group, N,N-dialkylsulfinamoyl group, N-arylsulfinamoyl group, N,N-diarylsulfinamoyl group, N-alkyl-N-arylsulfinamoyl group, sulfamoyl group, N-alkylsulfamoyl group, N,N-dialkylsulfamoyl group, N-arylsulfamoyl group, N,N-diarylsulfamoyl group, N-alkyl-N-arylsulfamoyl group, N-acylsulfamoyl group and its conjugate base group, N-alkylsulfonylsulfamoyl group (-SONHSO(alkyl)) and its conjugate base group, N-arylsulfonylsulfamoyl group (-SONHSO(aryl)) and its conjugate base group, N-alkylsulfonylcarbamoyl group (-CONHSO(alkyl)) and its conjugate base group, N-arylsulfonylcarbamoyl group (-CONHSO(aryl)) and its conjugate base group, alkoxysilyl group (-Si(Oalkyl)3), aryloxysilyl group (-Si(Oaryl)3), hydroxysilyl group (-Si(OH)3) and its conjugate base group, phosphono group (-PO3H2) and its conjugate base group, dialkylphosphono group (-PO3(alkyl) )2), diarylphosphono group (-PO3(aryl)2), alkylarylphosphono group (-PO3(alkyl)(aryl)), monoalkylphosphono group (-PO3H(alkyl)) and its conjugate base group, monoarylphosphono group (-PO3H(aryl)) and its conjugate base group, phosphonooxy group (-OPO3H2) and its conjugate base group, dialkylphosphonooxy group (-OPO3(alkyl)2), diarylphosphonooxy group (-OPO3(aryl)2), alkylarylphosphonooxy group (-OPO3(alkyl)(aryl)), monoalkylphosphonooxy group (-OPO3H(alkyl)) and its conjugate base group, monoarylphosphonooxy group (-OPO3H(aryl)) and its conjugate base group, cyano group, nitro group, aryl group, alkenyl group, alkynyl group, and alkyl group. Furthermore, each of the above groups may have further substituents (e.g., one or more of the above groups) if possible. For example, an aryl group which may have a substituent is also included as a group which can be selected from the substituent group Y. When the group selected from the substituent group Y has a carbon atom, the group has 1 to 20 carbon atoms, for example. The number of atoms other than hydrogen atoms contained in the group selected from the substituent group Y is 1 to 30, for example. Furthermore, these substituents may or may not bond to each other or to the group they substitute, if possible, to form a ring. For example, an alkyl group (or an alkyl group portion in a group containing an alkyl group as a partial structure, such as an alkoxy group) may be a cyclic alkyl group (cycloalkyl group) or an alkyl group having one or more cyclic structures as a partial structure.

[0018] <Curable composition> The curable composition of the present invention is a curable composition comprising a curable compound and inorganic particles, wherein the inorganic particles are selected from the group consisting of inorganic nitride particles and inorganic oxide particles, Meet requirement 1 or requirement 2 below. Requirement 1: The inorganic particles are surface-modified with at least one selected from the group consisting of a compound having a polymer chain and two or more alkoxysilyl groups, a hydrolyzate of the compound, and a hydrolyzed condensate of the compound. Requirement 2: The curable composition contains at least one selected from the group consisting of the compound, a hydrolyzate of the compound, and a hydrolysis condensate of the compound. Hereinafter, a compound having a polymer chain and two or more alkoxysilyl groups will also be referred to as a "specific compound," and at least one selected from the group consisting of the specific compound, a hydrolyzate of the specific compound, and a hydrolysis condensate of the specific compound will also be referred to as a "specific compound, etc."

[0019] The mechanism by which the curable composition of the present invention can form a thermally conductive material that has excellent thermal conductivity and excellent peel strength with respect to an adherend is not entirely clear, but the present inventors speculate as follows. The curable composition of the present invention satisfies the above requirement 1 or requirement 2. It is believed that the surface of the inorganic particles is likely to form bonds with the alkoxysilyl groups of the specific compound and groups generated by hydrolysis of the alkoxysilyl groups, or to have strong interactions with the groups. Therefore, when requirement 2 is met, the surface of the inorganic particles is likely to be modified by the specific compound. Furthermore, in both cases where requirement 1 and requirement 2 are met, the alkoxysilyl groups of the specific compound and the groups generated by hydrolysis of the alkoxysilyl groups are likely to be arranged close to the surface of the inorganic particles, and the polymer chains of the specific compound are likely to be arranged outward from the surface of the inorganic particles. Furthermore, it is believed that the above arrangement is easily achieved when there are two or more alkoxysilyl groups. The above-described arrangement allows the inorganic particles to be contained in the curable composition without impairing the thermal conductivity of the inorganic particles, and it is believed that the resulting thermally conductive material has excellent thermal conductivity. Furthermore, the polymer chains can enhance adhesion between the adherend (e.g., metal) and the resulting thermally conductive material, thereby reducing stress that occurs during curing. As a result, the resulting thermally conductive material is thought to have excellent peel strength.

[0020] Components that may be contained in the curable composition will be described below. The term "excellent thermal conductivity" used herein refers to a thermally conductive material formed from a curable composition having excellent thermal conductivity. The term "excellent peel strength" used herein refers to a thermally conductive material formed from a curable composition having excellent peel strength with an adherend.

[0021] [Curable compound] The curable composition of the present invention comprises a curable compound. The curable compound is a compound different from the above-mentioned specific compounds. Examples of the curable compound include a phenol compound, an epoxy compound, and a maleimide compound. It is also preferable that the curable compound does not contain a silicon atom or a group containing a silicon atom. (phenolic compounds) The phenol compound is a compound having one or more (preferably two or more, more preferably 2 to 10) phenolic hydroxyl groups. The phenol compound preferably has a triazine skeleton. The phenol compound "having a triazine skeleton" means that the phenol compound has one or more (preferably 1 to 5) triazine ring groups.

[0022] The phenol compound is preferably a compound represented by formula (Z).

[0023] [ka]

[0024] In the above formula (Z), when there are multiple groups represented by the same symbol, the multiple groups represented by the same symbol may be the same or different, unless otherwise specified.

[0025] In formula (Z), E 1 ~E 6 each independently represents a single bond, —NH—, or —NR—. R represents a substituent, and examples of the substituent include linear or branched alkyl groups having 1 to 5 carbon atoms. E 1 ~E 6 are each independently preferably —NH— or —NR—, more preferably —NH—.

[0026] In formula (Z), B 1 represents a single bond or a (k+1)-valent organic group. B 2 represents a single bond or an l+1-valent organic group. B 3 represents a single bond or an (m+1)-valent organic group. B 4 represents a single bond or an (n+1)-valent organic group. The values ​​of k, l, m, and n in the above k+1-valent organic group, l+1-valent organic group, m+1-valent organic group, and n+1-valent organic group are the same as the values ​​of k, l, m, and n specified in formula (Z). In addition, if r is 2 or more and the values ​​of m are different, B 3 The value of m in the (m+1) valent organic group represented by 3 X to which 3 The value of m is the same as the number of

[0027] B 1 ~B 4 Examples of the organic group represented by include groups in which j hydrogen atoms have been removed from a hydrocarbon having 1 to 20 carbon atoms and which may have a heteroatom. Here, j refers to k+1, l+1, m+1, or n+1. Here, examples of the hydrocarbon before removing j hydrogen atoms include one or more hydrocarbons selected from the group consisting of an aliphatic hydrocarbon having 1 to 20 carbon atoms which may have a substituent, an aliphatic ring having 3 to 20 carbon atoms which may have a substituent, and an aromatic ring having 3 to 20 carbon atoms which may have a substituent. In addition, the one or more hydrocarbons may further include -O-, -S-, -CO-, -NR N -(R N represents a hydrogen atom or a substituent.) and -SO2- may be combined with one or more divalent linking groups selected from the group consisting of -SO2- and -SO2-. Examples of aliphatic hydrocarbons having 1 to 20 carbon atoms include methane, ethane, propane, butane, pentane, hexane, and heptane. Examples of the aliphatic ring having 3 to 20 carbon atoms include a cyclohexane ring, a cycloheptane ring, a norbornane ring, and an adamantane ring. Examples of aromatic rings having 3 to 20 carbon atoms include aromatic hydrocarbons having 6 to 20 carbon atoms and aromatic heterocycles having 3 to 20 carbon atoms. Examples of aromatic hydrocarbons having 6 to 20 carbon atoms include a benzene ring, a naphthalene ring, and an anthracene ring, and examples of aromatic heterocycles having 3 to 20 carbon atoms include a furan ring, a pyrrole ring, a thiophene ring, a pyridine ring, a thiazole ring, a carbazole ring, an indole ring, and a benzthiazole ring.

[0028] In formula (Z), k, l, m, and n each independently represent an integer of 0 or greater, provided that the sum of k, l, r×m, and n is an integer of 2 or greater, preferably an integer of 2 to 12, and more preferably an integer of 4 to 8. The value of m in "r×m" is the average value of multiple possible m's. k, l, m and n each independently represent preferably an integer of 0 to 5, and more preferably an integer of 1 or 2. For example, k is preferably an integer of 1 or greater (e.g., an integer of 1 or 2, etc.), l is preferably an integer of 1 or greater (e.g., an integer of 1 or 2, etc.), m is preferably an integer of 1 or greater (e.g., an integer of 1 or 2, etc.), and n is preferably an integer of 1 or greater (e.g., an integer of 1 or 2, etc.). Note that if k is 0, B 1 is X 1 If l is 0, then B 2 is X 2 If m is 0, then B 3 is X 3 If n is 0, then B 4 is X 4 does not have. Also, B 1 If is a single bond, k is 1. 2 If is a single bond, l is 1. 3 If is a single bond, m is 1. 4 If is a single bond, n is 1.

[0029] L represents a divalent organic group. Examples of the divalent organic group include a divalent aromatic ring group which may have a substituent, a divalent aliphatic hydrocarbon group which may have a substituent, a divalent aliphatic ring group which may have a substituent, -N(R NA)-, -CO-, and combinations thereof. NA represents an organic group. The divalent organic group exemplified above further includes -O-, -S-, -N(R N )- and combinations thereof. R N represents a substituent. N Examples of the substituent represented by include a linear or branched alkyl group having 1 to 5 carbon atoms. Furthermore, examples of the substituent that the aromatic ring group, the aliphatic hydrocarbon group, and the aliphatic ring group may have include linear or branched alkyl groups having 1 to 5 carbon atoms.

[0030] Examples of the divalent aromatic ring group include a divalent aromatic hydrocarbon group having 6 to 20 carbon atoms and a divalent aromatic heterocyclic group having 3 to 20 carbon atoms. Examples of aromatic rings constituting a divalent aromatic hydrocarbon group having 6 to 20 carbon atoms include monocyclic aromatic rings such as a benzene ring; and polycyclic aromatic ring groups such as a naphthalene ring and an anthracene ring. Examples of aromatic heterocyclic rings constituting a divalent aromatic heterocyclic group having 3 to 20 carbon atoms include monocyclic aromatic rings such as a furan ring, a pyrrole ring, a thiophene ring, a pyridine ring, and a thiazole ring; and polycyclic aromatic rings such as a benzthiazole ring, a carbazole ring, and an indole ring. The divalent aromatic ring group represented by L includes groups obtained by removing two hydrogen atoms from the above examples.

[0031] Examples of divalent aliphatic hydrocarbon groups include alkylene groups having 1 to 12 carbon atoms, and specific examples include methylene, ethylene, propylene, butylene, pentylene, hexylene, methylhexylene, and heptylene groups.

[0032] Examples of the aliphatic ring constituting the divalent aliphatic ring group include a cyclohexane ring, a cycloheptane ring, a norbornane ring, and an adamantane ring. The aliphatic cyclic group represented by L may be any of the above-listed groups in which two hydrogen atoms have been removed.

[0033] a divalent aromatic ring group which may have a substituent, a divalent aliphatic hydrocarbon group which may have a substituent, a divalent aliphatic ring group which may have a substituent, or -O-, -S-, -NR N The group combining - or -CO- may be not only a divalent linking group consisting of a combination of two or more of these, but also a divalent linking group in which two or more groups of the same type (for example, aromatic ring groups) are combined via a single bond.

[0034] In the present invention, it is preferable that both ends of L are carbon atoms, in order to obtain a thermally conductive material with better thermal conductivity. The terminal carbon atoms may be part of a cyclic structure. In addition, in the present invention, in order to obtain a thermally conductive material with better thermal conductivity, it is preferable that L in the above formula (P2) is a divalent organic group having at least one selected from the group consisting of a divalent aromatic ring group which may have a substituent, a divalent aliphatic ring group which may have a substituent, and an alkylene group having two or more carbon atoms which may have a branch, and a divalent organic group having a divalent aromatic ring group which may have a substituent is more preferable in order to obtain better thermal conductivity.

[0035] In formula (Z), r is an integer of 0 or more. r is preferably an integer of 0 to 20, and more preferably an integer of 0 to 10.

[0036] In formula (Z), X 1 ~X 4 each independently represents an aromatic ring group having a phenolic hydroxyl group. The "aromatic ring group having a phenolic hydroxyl group" may be an aromatic ring group having one or more (e.g., 1 to 4) hydroxyl groups (phenolic hydroxyl groups) directly bonded to the aromatic ring. The aromatic ring group may or may not have a substituent other than the hydroxyl group. The aromatic ring group may be monocyclic or polycyclic, and may have a heteroatom as a ring member atom. The number of ring member atoms in the aromatic ring group is preferably 5 to 15, more preferably 6 to 10, and even more preferably 6. The aromatic ring group is preferably a benzene ring group. The substituent that the aromatic ring group may have other than the hydroxyl group is preferably a substituent having 1 to 6 carbon atoms, more preferably a hydrocarbon group having 1 to 6 carbon atoms, and even more preferably a linear or branched alkyl group having 1 to 6 carbon atoms.

[0037] In formula (Z), there are k X 1 , there are l X 2 , r×m pieces of X 3 and n X's 4 At least one of the groups is preferably an aromatic ring group having a phenolic hydroxyl group and a substituent located at the ortho-position relative to the phenolic hydroxyl group. The substituent may be located at only one or both of the ortho-positions relative to the phenolic hydroxyl group. The value of m in "r×m" is the average value of multiple possible m's. Furthermore, the "substituent located at the ortho position" is preferably a substituent having 1 to 6 carbon atoms, more preferably a hydrocarbon group having 1 to 6 carbon atoms, and even more preferably a linear or branched alkyl group having 1 to 6 carbon atoms. In other words, there are (k+l+r×m+n) X 1 ~X 4 At least one (preferably 30% or more, more preferably 50% or more, even more preferably 65% ​​or more; preferably 100% or less, more preferably 90% or less, even more preferably 80% or less) of the "aromatic ring groups having a phenolic hydroxyl group" represented by any one of the above may represent an "aromatic ring group having a phenolic hydroxyl group and a substituent arranged at the ortho-position of the phenolic hydroxyl group".

[0038] X 1 ~X 4 In the aromatic ring group having a phenolic hydroxyl group represented by the formula (I), the aromatic ring group other than "an aromatic ring group having a phenolic hydroxyl group and a substituent arranged at the ortho-position of the phenolic hydroxyl group" may or may not have a substituent other than a hydroxyl group (phenolic hydroxyl group). Examples of aromatic ring groups other than "aromatic ring groups having a phenolic hydroxyl group and a substituent positioned at the ortho-position of the phenolic hydroxyl group" include hydroxyphenyl groups. There are (k+l+r×m+n) instances of X 1 ~X 4 It is also preferred that at least one (e.g., one or two) of the "aromatic ring groups having a phenolic hydroxyl group" represented by any one of the above is an aromatic ring group other than the "aromatic ring group having a phenolic hydroxyl group and a substituent arranged at the ortho-position of the phenolic hydroxyl group". X 1 ~X 4 In the aromatic ring group having a phenolic hydroxyl group represented by the formula (I), the presence of aromatic ring groups other than "an aromatic ring group having a phenolic hydroxyl group and a substituent arranged at the ortho-position of the phenolic hydroxyl group" is thought to disrupt the symmetry of the compound as a whole, lower the melting point of the compound, and improve the handleability of the semi-cured film formed from the curable composition.

[0039] The phenol compound is also preferably a compound represented by formula (Z1). The phenol compound preferably contains a compound represented by formula (Z1), and the phenol compound may be the compound represented by formula (Z1) itself. The content of the compound represented by formula (Z1) is preferably 10 to 100 mass%, more preferably 25 to 100 mass%, and even more preferably 50 to 100 mass%, based on the total mass of the phenol compound.

[0040] [ka]

[0041] In formula (Z1), r represents an integer of 0 or greater. r is preferably an integer of 0 to 20, and more preferably an integer of 0 to 10. L represents a divalent organic group. The divalent organic group represented by L in formula (Z1) is, for example, the same as the divalent organic group represented by L in formula (Z1). R Z represents a hydrogen atom or a substituent. R ZThe substituent represented by the formula (I) is preferably a substituent having 1 to 6 carbon atoms, more preferably a hydrocarbon group having 1 to 6 carbon atoms, and even more preferably a linear or branched alkyl group having 1 to 6 carbon atoms. There are (3+r) Rs in formula (Z1) Z At least one of (preferably 30% or more, more preferably 50% or more, even more preferably 65% ​​or more; preferably 90% or less, more preferably 80% or less) may represent a substituent. There are (3+r) Rs in formula (Z1) Z At least one (for example, 1 to 2) of may represent a hydrogen atom. R in formula (Z1) z (Preferably, the substituent R z ) and OH-bonded benzene ring group, z (Preferably, the substituent R z ) is also preferably present at the para position relative to the NH bonded to the benzene ring group.

[0042] The phenol compound is also preferably a compound represented by formula (Z2). The phenol compound preferably contains a compound represented by formula (Z2), and the phenol compound may be the compound represented by formula (Z2) itself. The content of the compound represented by formula (Z2) is preferably 10 to 100 mass%, more preferably 25 to 100 mass%, and even more preferably 50 to 100 mass%, based on the total mass of the phenol compound.

[0043] [ka]

[0044] In formula (Z2), R Z represents a hydrogen atom or a substituent. Two Rs Z At least one of these groups preferably represents a substituent, and both of these groups preferably represent a substituent. R ZThe substituent represented by the following formula is preferably a substituent having 1 to 6 carbon atoms, more preferably a hydrocarbon group having 1 to 6 carbon atoms, and even more preferably an alkyl group having 1 to 6 carbon atoms. The alkyl group may be linear or branched, and is preferably unsubstituted. The two R in formula (Z2) z may be the same or different.

[0045] The phenol compound is also preferably a phenol compound having 3 to 7 hydroxyl groups in the molecule. The phenol compound having 3 to 7 hydroxyl groups in the molecule includes the compound represented by formula (Z3).

[0046] [ka]

[0047] In formula (Z3), m represents an integer of 1 to 6. m is more preferably 1 to 3, and 1 is even more preferred.

[0048] In formula (Z3), n1 and n2 each independently represent an integer of 1 or more. n1 and n2 each independently represent preferably 2 to 4, and more preferably 2 or 3. The sum of n1, n2 and m is 3 to 7.

[0049] In formula (Z3), R 1 ~R 6 each independently represents a hydrogen atom, a halogen atom, a carboxylic acid group, an alkyl group, an alkoxy group, or an alkoxycarbonyl group. The halogen atom is preferably a chlorine atom, a fluorine atom, a bromine atom, or an iodine atom, and more preferably a chlorine atom. The alkyl group may be linear or branched, preferably has 1 to 10 carbon atoms, and may be unsubstituted. It may or may not have a group. The alkyl group moiety in the alkoxy group and the alkyl group moiety in the alkoxycarbonyl group are the same as the alkyl group described above. Among them, R 1 and R 6 are each independently preferably a hydrogen atom or a halogen atom, more preferably a hydrogen atom or a chlorine atom, and even more preferably a hydrogen atom. R 2 ~R 5 are each independently preferably a hydrogen atom. In addition, in formula (Z3), R 4 If there are multiple R 4 may be the same or different. 5 If there are multiple R 5 may be the same or different.

[0050] In formula (Z3), Q represents an alkyl group, a phenyl group, a halogen atom, a carboxylic acid group, an alkoxy group, or an alkoxycarbonyl group. The alkyl group may be linear or branched, preferably has 1 to 10 carbon atoms, and may or may not have a substituent. The alkyl group moiety in the alkoxy group and alkoxycarbonyl group, and the alkyl group moiety in the alkoxycarbonyl group are the same as the alkyl group. The phenyl group may or may not have a substituent. The halogen atom is preferably a chlorine atom, a fluorine atom, a bromine atom, or an iodine atom. Among these, Q is preferably an alkyl group, more preferably a methyl group. When there are a plurality of Q's in formula (Z3), the plurality of Q's may be the same or different.

[0051] Examples of the phenol compound include benzene polyols such as bisphenol A, F, S, AD, benzene diol, and benzene triol, biphenyl aralkyl phenol resins, phenol novolac resins, cresol novolac resins, aromatic hydrocarbon formaldehyde resin-modified phenol resins, dicyclopentadiene phenol addition resins, phenol aralkyl resins, polyhydric phenol novolac resins synthesized from polyhydric hydroxy compounds and formaldehyde, naphthol aralkyl resins, trimethylol methane resins, tetraphenylol ethane resins, naphthol novolac resins, naphthol phenol co-condensed novolac resins, naphthol cresol co-condensed novolac resins, biphenyl-modified phenol resins, biphenyl-modified naphthol resins, aminotriazine-modified phenol resins, and alkoxy group-containing aromatic ring-modified novolac resins.

[0052] The molecular weight of the phenol compound is preferably from 225 to 2,000, more preferably from 225 to 1,000. When the molecular weight has a molecular weight distribution, the molecular weight is a weight average molecular weight.

[0053] The hydroxyl group content of the phenol compound is preferably 2.0 mmol / g or more, more preferably 4.0 mmol / g or more, and the upper limit is preferably 25.0 mmol / g or less, more preferably 10.0 mmol / g or less. The hydroxyl group content means the number of hydroxyl groups (preferably phenolic hydroxyl groups) contained in 1 g of the phenol compound. In addition to hydroxyl groups, the phenolic compound may or may not have an active hydrogen-containing group (e.g., carboxyl group) capable of polymerizing with an epoxy compound. The lower limit of the active hydrogen content of the phenolic compound (total content of hydrogen atoms in hydroxyl groups, carboxylic acid groups, etc.) is preferably 2.0 mmol / g or more, more preferably 4.0 mmol / g or more. The upper limit is preferably 25.0 mmol / g or less, more preferably 10.0 mmol / g or less.

[0054] The curable composition of the present invention may contain, in addition to the phenol compound, a compound having a group capable of reacting with an epoxy compound (also referred to as "other active hydrogen-containing compounds"). However, in the curable composition of the present invention, the mass ratio of the content of other active hydrogen-containing compounds to the content of the phenolic compound is preferably 0 to 1, more preferably 0 to 0.1, and even more preferably 0 to 0.05.

[0055] The content of the phenol compound in the curable composition is preferably from 3 to 90 mass %, more preferably from 5 to 50 mass %, and even more preferably from 7 to 40 mass %, based on the total solid content of the curable composition. The term "solids" refers to the components that form the thermally conductive material and does not include solvents. The components that form the thermally conductive material may be components that undergo a reaction (polymerization) to change their chemical structure when forming the thermally conductive material. Furthermore, any component that forms the thermally conductive material is considered to be a solid, even if it is in liquid form.

[0056] (epoxy compounds) An epoxy compound is a compound having at least one epoxy group (oxiranyl group) in one molecule. The epoxy group is a group obtained by removing one or more hydrogen atoms (preferably one hydrogen atom) from an oxirane ring. If possible, the epoxy group may further have a substituent (for example, a linear or branched alkyl group having 1 to 5 carbon atoms).

[0057] The number of epoxy groups that the epoxy compound has is preferably 2 or more, more preferably 2 to 1,000, and even more preferably 2 to 40, in one molecule.

[0058] The molecular weight of the epoxy compound is preferably at least 150, more preferably at least 300. The upper limit is preferably at most 100,000, more preferably at most 10,000. When the molecular weight has a molecular weight distribution, the molecular weight is a weight average molecular weight. In this specification, the number average molecular weight and weight average molecular weight are weight average molecular weights determined by gel permeation chromatography (GPC) in terms of polystyrene.

[0059] The epoxy group content of the epoxy compound is preferably 2.0 to 20.0 mmol / g, more preferably 5.0 to 15.0 mmol / g. The epoxy group content means the number of epoxy groups contained in 1 g of the epoxy compound. The epoxy compound also preferably has an aromatic ring group (preferably an aromatic hydrocarbon ring group). The content of the epoxy compound having an aromatic ring group is preferably from 5 to 100 mass %, more preferably from 50 to 100 mass %, and even more preferably from 70 to 100 mass %, based on the total amount of epoxy compounds.

[0060] The epoxy compound may or may not exhibit liquid crystallinity. That is, the epoxy compound may be a liquid crystal compound, or in other words, a liquid crystal compound having an epoxy group. Examples of the epoxy compound (which may be a liquid crystalline epoxy compound) include a compound having at least a partial rod-like structure (rod-like compound) and a compound having at least a partial discotic structure (discotic compound). The rod-shaped compounds and discotic compounds will be described in detail below.

[0061] -Rod-shaped compounds- Examples of epoxy compounds that are rod-shaped compounds include azomethines, azoxys, cyanobiphenyls, cyanophenyl esters, benzoic acid esters, cyclohexanecarboxylic acid phenyl esters, cyanophenylcyclohexanes, cyano-substituted phenylpyrimidines, alkoxy-substituted phenylpyrimidines, phenyldioxanes, tolanes, and alkenylcyclohexylbenzonitriles. In addition to the low molecular weight compounds described above, high molecular weight compounds can also be used. The high molecular weight compounds are polymerized low molecular weight rod-shaped compounds having reactive groups.

[0062] The rod-shaped compound is preferably a compound represented by formula (E1).

[0063] [ka]

[0064] In formula (E1), L E1 each independently represents a single bond or a divalent linking group. L E1 is preferably a divalent linking group. The divalent linking group is preferably -O-, -S-, -CO-, -NH-, -CH=CH-, -C≡C-, -CH=N-, -N=CH-, -N=N-, an optionally substituted alkylene group, or a group consisting of a combination of two or more of these, more preferably an -O-alkylene group- or an -alkylene group-O-. The alkylene group may be linear, branched, or cyclic, but is preferably a linear alkylene group having 1 to 2 carbon atoms. Multiple Ls E1 may be the same or different.

[0065] In formula (E1), L E2 are each independently a single bond, -CH=CH-, -CO-O-, -O-CO-, -C(-CH3)=CH-, -CH=C(-CH3)-, -CH=N-, -N=CH-, -N=N-, -C≡C-, -N=N + (-O - )-, -N + (-O - )=N-, -CH=N + (-O - )-, -N + (-O - )=CH—, —CH=CH—CO—, —CO—CH=CH—, —CH=C(—CN)— or —C(—CN)=CH—. L E2 are each independently preferably a single bond, -CO-O- or -O-CO-. L E2 If there are multiple L E2may be the same or different.

[0066] In formula (E1), L E3 each independently represents a single bond, an optionally substituted 5- or 6-membered aromatic ring group, an optionally substituted 5- or 6-membered non-aromatic ring group, or a polycyclic group consisting of these rings. L E3 Examples of aromatic and non-aromatic ring groups represented by the formula (I) include optionally substituted 1,4-cyclohexanediyl, 1,4-cyclohexenediyl, 1,4-phenylene, pyrimidine-2,5-diyl, pyridine-2,5-diyl, 1,3,4-thiadiazole-2,5-diyl, 1,3,4-oxadiazole-2,5-diyl, naphthalene-2,6-diyl, naphthalene-1,5-diyl, thiophene-2,5-diyl, and pyridazine-3,6-diyl groups. In the case of the 1,4-cyclohexanediyl group, it may be either a trans or cis structural isomer, or a mixture of any proportions. The trans isomer is preferred. L E3 is preferably a single bond, a 1,4-phenylene group or a 1,4-cyclohexenediyl group. L E3 The substituents on the group represented by the formula (I) are each independently preferably an alkyl group, an alkoxy group, a halogen atom, a cyano group, a nitro group or an acetyl group, more preferably an alkyl group (preferably having 1 carbon atom). When a plurality of substituents are present, the substituents may be the same or different. L E3 If there are multiple L E3 may be the same or different.

[0067] In formula (E1), pe represents an integer of 0 or more. If pe is an integer greater than or equal to 2, there are multiple (-L E3 -L E2 -) may be the same or different. pe is preferably 0 to 2, more preferably 0 or 1, and even more preferably 0.

[0068] In formula (E1), L E4 each independently represents a substituent. The substituents are each independently preferably an alkyl group, an alkoxy group, a halogen atom, a cyano group, a nitro group or an acetyl group, more preferably an alkyl group (preferably having 1 carbon atom). Multiple Ls E4 may be the same or different. In addition, when le, which will be explained next, is an integer of 2 or more, the same (L E4 ) le There are multiple L's in E4 may be the same or different.

[0069] In formula (E1), each le independently represents an integer of 0 to 4. Each le is preferably 0 to 2. Multiple le's may be the same or different.

[0070] In addition, in the compound represented by formula (E1), two "epoxy groups -L E1 Also preferred are compounds in which one or both of the "-" groups are replaced with a diglycidylaminoalkylene group (preferably a diglycidylaminomethylene group).

[0071] The rod-like compound preferably has a biphenyl skeleton, since the resulting thermally conductive material has better thermal conductivity. In other words, the epoxy compound preferably has a biphenyl skeleton, and in this case, the epoxy compound is preferably a rod-like compound.

[0072] -Disc-shaped compounds- The discotic epoxy compound has at least a partial discotic structure. The discotic structure has at least an alicyclic ring or an aromatic ring. In particular, when the discotic structure has an aromatic ring, the discotic compound can form a columnar structure by forming a stacking structure due to intermolecular π-π interactions. Specific examples of the discotic structure include the triphenylene structure described in Angew. Chem. Int. Ed. 2012, 51, 7990-7993 or JP-A-7-306317, and the tri-substituted benzene structures described in JP-A-2007-002220 and JP-A-2010-244038.

[0073] If a discotic compound is used as the epoxy compound, a thermally conductive material with high thermal conductivity can be obtained. The reason for this is thought to be that while rod-shaped compounds can only conduct heat linearly (one-dimensionally), discotic compounds can conduct heat planarly (two-dimensionally) in the normal direction, which increases the number of heat conduction paths and improves thermal conductivity.

[0074] The discotic compound preferably has three or more epoxy groups. A cured product of a curable composition containing a discotic compound having three or more epoxy groups tends to have a high glass transition temperature and high heat resistance. The number of epoxy groups contained in the discotic compound is preferably 8 or less, more preferably 6 or less.

[0075] Examples of the discotic compound include compounds in which at least one (preferably three or more) of the terminals is an epoxy group, such as those described in C. Destrade et al., Mol. Crysr. Liq. Cryst., vol. 71, page 111 (1981); Quarterly Review of Chemistry, No. 22, edited by the Chemical Society of Japan, Chemistry of Liquid Crystals, Chapter 5, Chapter 10, Section 2 (1994); B. Kohne et al., Angew. Chem. Soc. Chem. Comm., page 1794 (1985); J. Zhang et al., J. Am. Chem. Soc., vol. 116, page 2655 (1994) and Japanese Patent No. 4592225. Examples of the discotic compound include the triphenylene structure described in Angew. Chem. Int. Ed. 2012, 51, 7990-7993 and JP-A-7-306317, and compounds in which at least one (preferably three or more) of the terminals of a trisubstituted benzene structure described in JP-A-2007-002220 and JP-A-2010-244038 is an epoxy group.

[0076] -Other epoxy compounds- In addition to the above-mentioned epoxy compounds, compounds represented by the formula (Z), (Z1), or (Z2) described in the description of the phenolic compounds in which the phenolic hydroxy group is replaced with an epoxy-containing group can also be used as the epoxy compound. The epoxy-containing group is a group that is an epoxy group itself or a monovalent group that partially contains an epoxy group. The monovalent group partially containing an epoxy group is a group having one or more (preferably 1 to 8) epoxy groups within the entire group. The monovalent group containing an epoxy group as a part thereof is "-(divalent hydrocarbon group) M1 -(-O-divalent hydrocarbon group-) M2 -epoxy group" is preferred. In the above group, M1 represents 0 or 1. M2 represents an integer of 1 or more (preferably 1 to 10). Examples of the divalent hydrocarbon group in the above group include alkylene groups (preferably having 1 to 6 carbon atoms), alkenylene groups (-CH=CH-, etc., preferably having 2 to 6 carbon atoms), alkynylene groups (-C≡C-, etc., preferably having 2 to 6 carbon atoms), arylene groups (phenylene group, etc., preferably having 6 to 15 carbon atoms), and groups formed by combining these. The divalent hydrocarbon group may or may not have a substituent, and the divalent hydrocarbon group may further have an epoxy-containing group as a substituent. The divalent hydrocarbon groups, which may be present in plurality, may be the same or different.

[0077] Other epoxy compounds include, for example, bisphenol A-type epoxy compounds, which are glycidyl ethers of bisphenol A, F, S, AD, etc., such as bisphenol A-type epoxy compounds, bisphenol F-type epoxy compounds, bisphenol S-type epoxy compounds, and bisphenol AD-type epoxy compounds; hydrogenated bisphenol A-type epoxy compounds, hydrogenated bisphenol AD-type epoxy compounds, etc.; phenol novolac-type glycidyl ethers (phenol novolac-type epoxy compounds), cresol novolac-type glycidyl ethers (cresol novolac-type epoxy compounds), bisphenol A novolac-type glycidyl ethers, etc.; dicyclopentadiene-type glycidyl ethers (dicyclopentadiene-type epoxy compounds); dihydroxypentadiene-type glycidyl ethers (dihydroxypentadiene-type epoxy compounds); polyhydroxybenzene-type glycidyl ethers (polyhydroxybenzene-type epoxy compounds) such as glycidyl ethers of dihydroxybenzenes such as resorcinol; benzenepolycarboxylic acid-type glycidyl esters (benzenepolycarboxylic acid-type epoxy compounds); trisphenolmethane-type epoxy compounds; phenoxy resins, etc.; and acrylic resins having epoxy groups on their side chains. A compound in which one or more of the glycidyl ether groups and / or glycidyl ester groups in each of the above-mentioned compounds are replaced with a diglycidylamino group or a diglycidylaminoalkylene group (such as a diglycidylaminomethylene group) may be used as the epoxy compound. Each of the above compounds may have a substituent. For example, the aromatic ring group, cycloalkane ring group, and / or alkylene group contained in each of the above compounds may have a substituent other than a glycidyl ether group, a glycidyl ester group, a diglycidylamino group, and / or a diglycidylaminoalkylene group.

[0078] The epoxy compound preferably contains at least one selected from the group consisting of polyhydroxybenzene-type glycidyl ethers, bisphenol F-type glycidyl ethers, epoxy compounds represented by formula (DN), rod-shaped compounds (preferably rod-shaped compounds having a biphenyl skeleton), discotic compounds (preferably discotic compounds having a biphenylene ring as the central ring, discotic compounds having a triazine ring as the central ring, or discotic compounds having a benzene ring as the central ring), phenol novolac-type glycidyl ethers, and phenoxy resins.

[0079] The content of the epoxy compound in the curable composition is preferably from 3 to 90 mass %, more preferably from 5 to 50 mass %, and even more preferably from 7 to 40 mass %, based on the total solid content of the curable composition.

[0080] (Maleimide compounds) A maleimide compound is a compound having one or more maleimide groups. The number of maleimide groups contained in the maleimide compound is preferably 1 to 100, more preferably 2 to 10, and even more preferably 2. The maleimide compound may be either a high molecular weight compound or a low molecular weight compound. For example, the molecular weight of the maleimide compound is preferably 100 to 3,000, more preferably 200 to 2,000, and even more preferably 300 to 1,000.

[0081] The maleimide group contained in the maleimide compound is preferably a group represented by the following formula (M).

[0082] [ka]

[0083] In formula (M), * represents a bonding position. X and Y each independently represent a hydrogen atom or a substituent. X and Y are each preferably a hydrogen atom.

[0084] The maleimide compound is also preferably a compound having one or more (preferably 1 to 10) aromatic ring groups (such as benzene ring groups). The maleimide compound is also preferably a compound having a mesogenic group. Examples of the mesogenic group include the mesogenic group represented by M in formula (XXI) and the mesogenic group represented by formula (XXII). The maleimide compound is preferably a compound represented by the following formula (1):

[0085] [ka]

[0086] In formula (1), m represents 0 or 1. m is preferably 1. n represents 0 or 1. n is preferably 1.

[0087] In formula (1), R 1 and R 2 each independently represents a hydrogen atom or a substituent. The substituent is preferably an alkyl group, which may be linear or branched and preferably has 1 to 10 carbon atoms. R when it is a substituent 1 and / or R 2 is preferably present, for example, at a position adjacent to the maleimide group on the benzene ring group. R 1 and R 2 If both are substituents, R 1 and R 2 are preferably different substituents, for example, R 1 is a methyl group and R 2 It is also preferred that is an ethyl group.

[0088] In formula (1), L 1 represents a divalent linking group. Examples of the divalent linking group include an ether group (-O-), a carbonyl group (-CO-), an ester group (-COO-), a thioether group (-S-), -SO2-, -NR- (R is a hydrogen atom or an alkyl group), a divalent aliphatic hydrocarbon group (for example, an alkylene group, a cycloalkylene group, an alkenylene group (-CH=CH-, etc.), an alkynylene group (-C≡C-, etc.)), a divalent aromatic ring group (an arylene group and a heteroarylene group), and a group formed by combining these. In formula (1), L 1 The number of carbon atoms is preferably 1 or more, more preferably 1 to 100, and even more preferably 3 to 15.

[0089] L 1 As the group, a mesogenic group is preferred. Examples of the mesogenic group include a mesogenic group represented by M in formula (XXI) and a mesogenic group represented by formula (XXII).

[0090] L 1 teeth,"* p -(L 2 -Ar) k -* q " is preferred. * q represents the bonding position on the side directly bonding to the maleimide group, and * p represents the opposite binding position. k represents an integer of 1 or more, preferably 1 to 10, and more preferably 1. L 2 is a single bond, -C(R 3 )(R 4 )-, -O- or -CO-, -C(R 3 )(R 4 )- is preferred. R 3 and R 4 each independently represents a hydrogen atom or a substituent, and is preferably an alkyl group (which may be linear or branched and has, for example, 1 to 10 carbon atoms). Ar represents an arylene group. The number of ring atoms in the arylene group is preferably 6 to 15, more preferably 6. When the arylene group has a substituent, the number of atoms is preferably 1 to 4, more preferably 1 or 2. The substituent that the arylene group may have is preferably an alkyl group (which may be linear or branched, and has, for example, 1 to 10 carbon atoms). Examples of structures that Ar can have include R 1 and R 2 and a structure that can be a benzene ring group bonded to the L 2 and when there are multiple Ar, there are multiple L 2 The Ar groups and the Ar groups present in plural may be the same or different.

[0091] In formula (1) when n is 1, R 1 and R 2 On the benzene ring group bonded to the maleimide group, 1 ) m The two groups represented by the "-maleimide group" may be positioned at the ortho position, the meta position, or the para position relative to each other. The two groups are preferably positioned at the meta position or the para position.

[0092] The compound represented by formula (1) is such that m represents 1, n represents 1, and L 1 The divalent linking group represented by the following formula preferably has 3 to 15 carbon atoms.

[0093] The maleimide compounds may be used alone or in combination of two or more. The content of the maleimide compound is preferably 0.1 to 40 mass%, more preferably 1 to 15 mass%, and even more preferably 3.5 to 8 mass%, relative to the total solid content of the curable composition, and from the viewpoint of better handleability of the semi-cured film formed from the curable composition, is further preferably 3.5 to 8 mass%. In order to obtain a thermally conductive material with better thermal conductivity and / or insulating properties, the content of the maleimide compound is preferably 6% by mass or more (for example, 6 to 12% by mass) relative to the total solid content of the curable composition. When the curable composition contains an epoxy compound, the content of the maleimide compound is, for example, 1 to 200 mass%, preferably 5 to 100 mass%, more preferably 10 to 70 mass%, and even more preferably 20 to 60 mass%, relative to the total content of the epoxy compound and the phenol compound. The content of the maleimide compound is, for example, 1 to 500% by mass, preferably 20 to 300% by mass, more preferably 50 to 200% by mass, and even more preferably 70 to 130% by mass, relative to the content of the phenol compound.

[0094] (Relationship between phenolic compounds and epoxy compounds) When the curable composition contains an epoxy compound and a phenolic compound, it is preferable that the curable composition satisfies at least one of the following requirements: the phenolic compound contains a phenolic compound having a triazine skeleton (requirement A), and the epoxy compound contains an epoxy compound having a triazine skeleton (requirement B). The curable composition may satisfy only requirement A, may satisfy only requirement B, or may satisfy both requirements A and B.

[0095] The phenol compound and epoxy compound "having a triazine skeleton" means that the compound has one or more (for example, 1 to 5) triazine ring groups. Examples of the phenol compound having a triazine skeleton include the compounds represented by the formula (Z), the compounds represented by the formula (Z1), and the compounds represented by the formula (Z2). Examples of epoxy compounds having a triazine skeleton include a compound represented by formula (Z) in which the phenolic hydroxyl group is replaced with an epoxy-containing group, a compound represented by formula (Z1) in which the phenolic hydroxyl group is replaced with an epoxy-containing group, and a compound represented by formula (Z2) in which the phenolic hydroxyl group is replaced with an epoxy-containing group.

[0096] When the phenol compound contains a phenol compound having a triazine skeleton (for example, when requirement A is satisfied), the content thereof is more than 0 mass % and not more than 100 mass %, preferably 30 to 100 mass %, more preferably 60 to 100 mass %, and even more preferably 90 to 100 mass %, based on the total mass of the phenol compounds. Note that when the curable composition contains an epoxy compound, and the epoxy compound contains an epoxy compound having a triazine skeleton (when requirement B is satisfied), it is also preferable that the content of the phenol compound having a triazine skeleton is outside the above-mentioned preferred range. When the curable composition contains an epoxy compound, and the epoxy compound contains an epoxy compound having a triazine skeleton (when requirement B is satisfied), the content thereof is more than 0% by mass and not more than 100% by mass, preferably 30 to 100% by mass, more preferably 60 to 100% by mass, and even more preferably 90 to 100% by mass, based on the total mass of the epoxy compounds. Note that when the phenol compound contains a phenol compound having a triazine skeleton (i.e., when requirement A is satisfied), the content of the epoxy compound having a triazine skeleton may be outside the above-mentioned preferred range.

[0097] When the curable composition contains an epoxy compound, it is also preferable that at least a part of the phenol compound and the epoxy compound is a compound other than a compound having a triazine skeleton. All or part of the phenol compounds may be compounds other than those having a triazine skeleton, and all or part of the epoxy compounds may be compounds other than those having a triazine skeleton. When the curable composition contains an epoxy compound, from the viewpoint of adjusting the crosslink density and further improving the effects of the present invention, the total content of the phenol compound having a triazine skeleton and the epoxy compound having a triazine skeleton is preferably more than 0 mass% and less than 100 mass%, more preferably 1 to 90 mass%, and still more preferably 5 to 80 mass%, based on the total content of all phenol compounds and all epoxy compounds.

[0098] In addition, the total content of the epoxy compound and the phenol compound in the curable composition is preferably 3 to 90 mass %, more preferably 5 to 50 mass %, and even more preferably 7 to 40 mass %, based on the total solid content of the curable composition.

[0099] The ratio of the total number of epoxy groups contained in the epoxy compound to the total number of hydroxyl groups (preferably phenolic hydroxyl groups) contained in the phenol compound (number of epoxy groups / number of hydroxyl groups) is often 0.03 to 33, preferably 0.4 to 2.5, more preferably 0.6 to 1.5, and even more preferably 0.8 to 1.3. In other words, the ratio of the contents of the phenol compound and the epoxy compound in the curable composition is preferably such that the above-mentioned "number of epoxy groups / number of phenolic hydroxyl groups" falls within the above-mentioned range.

[0100] The equivalent ratio of epoxy groups to active hydrogens in the epoxy compound (number of epoxy groups / number of active hydrogens) is often 0.03 to 33, preferably 0.4 to 2.5, more preferably 0.6 to 1.5, and even more preferably 0.8 to 1.3. The active hydrogen may be an active hydrogen derived from a phenolic hydroxyl group, or may be an active hydrogen of another active hydrogen-containing compound.

[0101] The ratio of the total number of epoxy groups contained in the epoxy compound to the total number of hydroxyl groups (preferably phenolic hydroxyl groups) contained in the phenol compound (number of epoxy groups / number of hydroxyl groups) is preferably 1.1 to 3.0, more preferably 1.2 to 2.0, and even more preferably 1.3 to 1.8. In particular, when the curable composition contains the maleimide compound, the ratio preferably falls within the above range. When the ratio is equal to or greater than a predetermined value, flexibility is introduced into the semi-cured film formed from the curable composition, improving storage stability, and the semi-cured film has good handleability even after a certain period of time has passed since its formation. When the ratio is equal to or less than a predetermined value, the heat resistance of the thermal conductive material formed from the curable composition is superior. Such an improvement effect is particularly remarkable when the curable composition contains a maleimide compound described below.

[0102] [Inorganic particles] The curable composition of the present invention comprises inorganic particles selected from the group consisting of inorganic nitride particles and inorganic oxide particles.

[0103] Examples of inorganic nitrides include boron nitride (BN), carbon nitride (CN), silicon nitride (SiN), gallium nitride (GaN), indium nitride (InN), aluminum nitride (AlN), chromium nitride (CrN), copper nitride (CuN), iron nitride (FeN), iron nitride (FeN), lanthanum nitride (LaN), lithium nitride (LiN), magnesium nitride (MgN), molybdenum nitride (MoN), niobium nitride (NbN), tantalum nitride (TaN), titanium nitride (TiN), tungsten nitride (WN), tungsten nitride (WN), yttrium nitride (YN), and zirconium nitride (ZrN). Among these, inorganic nitride particles are preferred because of their excellent thermal conductivity. Materials constituting inorganic nitride particles with excellent thermal conductivity include, for example, aluminum nitride (AlN) and boron nitride (BN), with boron nitride being preferred.

[0104] Examples of inorganic oxides include zirconium oxide (ZrO2), titanium oxide (TiO2), silicon oxide (SiO2), aluminum oxide (Al2O3), iron oxide (Fe2O3, FeO, Fe3O4), copper oxide (CuO, Cu2O), zinc oxide (ZnO), yttrium oxide (Y2O3), niobium oxide (Nb2O5), molybdenum oxide (MoO3), indium oxide (In2O3, I Examples of inorganic oxides include tin oxide (SnO), tantalum oxide (TaO), tungsten oxide (WO, WO), lead oxide (PbO, PbO), bismuth oxide (BiO), cerium oxide (CeO, CeO), antimony oxide (SbO, SbO), germanium oxide (GeO, GeO), lanthanum oxide (LaO), and ruthenium oxide (RuO). The inorganic oxide may be an oxide produced by oxidizing a metal prepared as a non-oxide under environmental conditions. Among these, inorganic oxide particles are preferred because of their excellent thermal conductivity. Materials constituting inorganic oxide particles with excellent thermal conductivity include, for example, silicon oxide (silica, SiO2) and aluminum oxide (alumina, Al2O3), with alumina being preferred.

[0105] Of these, inorganic nitride particles are preferred as the inorganic particles, and boron nitride particles are more preferred.

[0106] Inorganic particle diameter D 50 is often 10 μm or more, preferably 20 μm or more, and more preferably 30 μm or more. The upper limit is preferably 500 μm or less, more preferably 300 μm or less, even more preferably 200 μm or less, and particularly preferably 100 μm or less. In addition, D 50means the median diameter, and can be measured, for example, using a Mastersizer 2000 (manufactured by Malvern Panalytical). When commercially available inorganic particles are used, the median diameter listed in the catalog value can be used. Furthermore, the median diameter can be determined by measuring the particle diameter of 100 particles selected at random using an electron microscope (e.g., a scanning electron microscope or a transmission electron microscope), and then determining the frequency distribution. When the inorganic particles are not spherical, the median diameter can be determined by using the longest diameter of the inorganic particles as the particle diameter.

[0107] The inorganic particles may have a rice grain, sphere, cube, spindle, scale, aggregate (aggregate), or irregular shape, with aggregates being preferred. The inorganic particles are also preferably aggregates of inorganic nitride particles (more preferably boron nitride particles).

[0108] The inorganic particles are preferably surface-treated. The surface treatment means a treatment different from the surface modification with a specific compound, a hydrolyzate of a specific compound, or a hydrolysis condensate of a specific compound in requirement 1 above. By carrying out such treatment, functional groups are introduced onto the surfaces of the inorganic particles, making it easier for the inorganic particles to interact with the curable compound and / or the specific compound described below, etc., and it is believed that this results in better thermal conductivity and peel strength. Examples of surface treatments include plasma treatments (e.g., vacuum plasma treatment, atmospheric pressure plasma treatment, and aqua plasma treatment), ultraviolet irradiation treatment, corona treatment, electron beam irradiation treatment, ozone treatment, baking treatment, flame treatment, and oxidizing agent treatment. The oxidizing agent treatment may be carried out under either acidic or basic conditions (e.g., pH 12 to 14). Among these, the surface treatment is preferably an oxidizing agent treatment carried out under basic conditions.

[0109] The inorganic particles may be used alone or in combination of two or more kinds. The content of the inorganic particles is preferably 20% by mass or more, more preferably 50% by mass or more, even more preferably 60% by mass or more, and particularly preferably 70% by mass or more, based on the total solid content of the curable composition. The upper limit is preferably less than 100% by mass, more preferably 95% by mass or less, and even more preferably 85% by mass or less.

[0110] [Requirements 1 and 2] The curable composition of the present invention satisfies the following requirement 1 or requirement 2. Requirement 1: The inorganic particles are surface-modified with at least one selected from the group consisting of a specific compound (a compound having a polymer chain and two or more alkoxysilyl groups), a hydrolyzate of a specific compound, and a hydrolyzed condensate of a specific compound. Requirement 2: The curable composition contains at least one selected from the group consisting of the specific compound, a hydrolyzate of the specific compound, and a hydrolysis condensate of the specific compound. First, the specific compound (a compound having a polymer chain and two or more alkoxysilyl groups) used for the surface modification of Requirement 1 or contained in the curable composition of Requirement 2, the hydrolyzate of the specific compound, and the hydrolysis condensate of the specific compound will be described below.

[0111] (Specific compound) The specific compound is a compound having a polymer chain and two or more alkoxysilyl groups. The specific compound is not particularly limited as long as it has a polymer chain and two or more alkoxysilyl groups, but a compound represented by the following formula (a) is preferred in terms of excellent thermal conductivity and peel strength.

[0112] [ka]

[0113] In formula (a), Y a represents a polymer chain. Y aThe polymer chain represented by is not particularly limited, but examples thereof include vinyl polymers, ester polymers, ether polymers, urethane polymers, amide polymers, epoxy polymers, and silicone polymers. The polymer chain preferably contains carbon atoms in the main chain of the polymer chain. The number of carbon atoms in the main chain of the polymer chain is preferably 30% or more, more preferably 50% or more, and even more preferably 70% or more, based on the total atoms constituting the main chain of the polymer chain. The upper limit can be, and may be, 100%. The main chain refers to the relatively longest bond chain in the polymer chain.

[0114] Above Y a The polymer chain represented by the formula (1) preferably has a repeating unit represented by the following formula (y):

[0115] [ka]

[0116] In formula (y), R y1 , R y2 and R y3 each independently represents a hydrogen atom or a monovalent substituent. R y1 , R y2 and R y3 Examples of the substituent represented by include groups selected from the above-mentioned group Y of substituents, and specific examples thereof include an alkyl group having 1 to 3 carbon atoms which may further have a substituent, a halogen atom, and a hydroxy group. The alkyl group having 1 to 3 carbon atoms which may further have a substituent is preferably an unsubstituted alkyl group having 1 to 3 carbon atoms, and more preferably a methyl group. Among them, R y1 and R y2 represents a hydrogen atom, and R y3 It is preferable that represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms which may further have a substituent (preferably a methyl group).

[0117] In formula (y), L y1represents a single bond or a divalent linking group. L y1 Examples of the divalent linking group represented by include an ether group (-O-), a carbonyl group (-CO-), an ester group (-COO-), a thioether group (-S-), -SO2-, and -NR T -(R T represents a hydrogen atom, an alkyl group, or an aryl group. T -, aliphatic hydrocarbon groups which may have a divalent substituent (for example, alkylene groups, cycloalkylene groups, alkenylene groups (-CH=CH-, etc.), alkynylene groups (-C≡C-, etc.), etc.), aromatic ring groups which may have a divalent substituent (for example, arylene groups, heteroarylene groups), etc.), and groups formed by combining these. Examples of the substituents for the aliphatic hydrocarbon groups which may have a divalent substituent and the aromatic ring groups which may have a divalent substituent include groups selected from the above-mentioned substituent group Y. Among them, -O-, -S-, -COO-, -NR T -,-CONR T -, an alkylene group, a phenylene group, or a group formed by combining two or more of these is preferred. T is preferably a hydrogen atom, a methyl group, or an ethyl group. Examples of the group combining two or more of the above include -COO-alkylene group-, -COO-alkylene group-L T1 -Alkylene group-(L T1 represents any one of -O-, -COO- and -OCO-), -COO- alkylene group -L T1 -Alkylene group -S-, -COO-(CH2-CH2-O-) k (k is an integer of 1 to 10), -COO-alkylene group -OCO-, -COO-alkylene group -COO-, and -CONR T -L T2 -(L T2 represents an alkylene group or a phenylene group.

[0118] In formula (y), Z yrepresents a monovalent substituent. Examples of the monovalent substituent include groups selected from the above-mentioned substituent group Y. Z y Preferred examples of the group represented by the formula (I) include an alkyl group, an alkoxy group, an aromatic ring group, an epoxy group (oxiranyl group), a hydroxy group, a carboxy group, and an amino group. Z y The group represented by the formula (I) is preferably a polymerizable group capable of undergoing a polymerization reaction, such as an acryloyl group, a methacryloyl group, an oxiranyl group, or a vinyl group. The polymerizable group is preferably an oxiranyl group. The alkyl group in the alkyl group and alkoxy group may be linear, branched, or cyclic. The number of carbon atoms in the alkyl group and alkoxy group is not particularly limited, but is preferably 1 to 10, and more preferably 1 to 5. The aromatic ring group includes an aromatic hydrocarbon group and an aromatic heterocyclic group. Examples of the ring constituting the aromatic hydrocarbon group include a benzene ring and a naphthalene ring. Examples of rings constituting the aromatic heterocyclic group include a furan ring, a pyrrole ring, an imidazole ring, a pyrazole ring, a triazole ring, a thiophene ring, a pyridine ring, a benzimidazole ring, a benztriazole ring, and a benzthiazole ring. Of these, a benzimidazole ring, a benztriazole ring, or a benzthiazole ring is preferred. The alkyl group, the alkyl group in the alkoxy group, and the aromatic ring group may further have a monovalent substituent. Examples of the monovalent substituent include groups selected from the above-mentioned substituent group Y. The aromatic ring group is preferably an aromatic hydrocarbon group, and is preferably a benzimidazole ring, a benztriazole ring, or a benzthiazole ring in terms of excellent peel strength.

[0119] In formula (y), R y2 and Z y may be bonded to form a ring. y1 , Z y , R y2 , R in formula (y) y2and the carbon atom bonded to L in formula (y). y1 The carbon atoms to which it is bonded form a ring. R y2 and Z y A preferred embodiment in which the repeating units represented by the following formula (yy) are bonded to form a ring is a repeating unit represented by the following formula (yy): That is, it is also preferred that the repeating unit represented by the formula (y) is a repeating unit having an acid anhydride group represented by the following formula (yy):

[0120] [ka]

[0121] In formula (yy), R y1 and R y3 each independently represents a hydrogen atom or a monovalent substituent, and preferred embodiments thereof are the same as those in formula (y). When the polymer chain contains a repeating unit having an acid anhydride group represented by the formula (yy), peel strength is excellent, which is preferable.

[0122] In addition, the above Y a The polymer chain represented by the formula (I) preferably has a repeating unit having an acid anhydride group or a repeating unit having an aromatic heterocyclic group. The repeating unit having an acid anhydride group may be any repeating unit having an acid anhydride group (-CO-O-CO-) in the repeating unit, and examples thereof include repeating units having an acid anhydride group represented by the above formula (yy). The repeating unit having an aromatic heterocyclic group may have an aromatic heterocyclic group in the repeating unit, and for example, Z in formula (y) y is an aromatic heterocyclic group.

[0123] In formula (a), L a1 and L a2 each independently represents a single bond or a divalent linking group. L a1 and L a2Examples of the divalent linking group represented by include an ether group (-O-), a carbonyl group (-CO-), an ester group (-COO-), a thioether group (-S-), -SO2-, -NR- (R represents a hydrogen atom, an alkyl group, or an aryl group), a divalent aliphatic hydrocarbon group (for example, an alkylene group, a cycloalkylene group, an alkenylene group (-CH=CH-, etc.), and an alkynylene group (-C≡C-, etc.)), a divalent aromatic ring group (for example, an arylene group and a heteroarylene group), and a group formed by combining these. L a1 and L a2 is preferably a group formed by combining two or more groups selected from -CO-, -O-, -S-, and an alkylene group. a1 and L a2 Examples of the alkylene group include -CO-alkylene-, -CO-alkylene-O-alkylene-, and -CO-alkylene-S-alkylene-. The alkylene group may be either linear or branched. The alkylene group preferably has 1 to 10 carbon atoms, and more preferably 1 to 5 carbon atoms.

[0124] In formula (a), n a represents an integer of 1 or greater. n a is preferably 1 to 5, more preferably 2 to 4, and even more preferably 2 or 3.

[0125] In formula (a), m a represents an integer of 2 or greater. m a is preferably 2 to 5, more preferably 2 to 4, and further preferably 3 or 4 in terms of peel strength.

[0126] In formula (a), A a is n a +m a represents a valent linking group. n a +m a is 3 or more, preferably 3 to 10, more preferably 4 to 8, still more preferably 4 to 6, and particularly preferably 6. Aa represents n a +m a The valent linking group is not particularly limited. A a represents n a +m a The valent linking group may or may not have a cyclic structure. The cyclic structure may be an aromatic ring or an alicyclic ring. a represents n a +m a The valent linking group preferably does not have a cyclic structure. n having no cyclic structure a +m a The valence of the linking group is preferably a linking group obtained by removing hydrogen atoms from a hydroxy group of the polyol. The polyol may contain an ether bond (-O-) or an amine bond (-N<). The hydrogen atoms of the hydroxy group of the polyol may be partially or completely removed. However, the valence of the linking group should be 3 or more. Examples of linking groups derived from polyols include glycerin, trimethylolpropane, triethanolamine, erythritol, pentaerythritol, xylitol, mannitol, and dipentaerythritol. Of these, linking groups obtained by removing a hydrogen atom from a hydroxy group in trimethylolpropane, pentaerythritol, or dipentaerythritol are preferred.

[0127] In formula (a), X a represents an alkoxysilyl group. The alkoxysilyl group refers to a group represented by the following formula (x):

[0128] [ka]

[0129] In formula (x), * represents the bonding position to a specific compound. In formula (x), R x1 , R x2 and R x3each independently represents an alkoxy group, a hydroxy group, or an alkyl group, provided that R x1 , R x2 and R x3 At least one of these represents an alkoxy group. Above R x1 , R x2 and R x3 The alkyl group of the alkoxy group represented by may be linear or branched, but is preferably linear. The alkyl group of the alkoxy group may have a substituent, but is preferably an unsubstituted alkyl group. The number of carbon atoms of the alkyl group of the alkoxy group is preferably 1 to 6, more preferably 1 to 3, and even more preferably 1 or 2. That is, R x1 , R x2 and R x3 The alkoxy group represented by is preferably a methoxy group or an ethoxy group. Above R x1 , R x2 and R x3 The alkyl group represented by R may be linear or branched, but is preferably linear. x1 , R x2 and R x3 The alkyl group represented by may have a substituent, but is preferably an unsubstituted alkyl group. x1 , R x2 and R x3 The alkyl group represented by the formula (I) preferably has 1 to 6 carbon atoms, more preferably 1 to 3 carbon atoms, and even more preferably 1 or 2 carbon atoms.

[0130] X a A preferred embodiment of the alkoxysilyl group represented by R x1 , R x2 and R x3 and R x1 , R x2 and R x3 In a preferred embodiment, all of the groups are methoxy groups or ethoxy groups.

[0131] The weight average molecular weight of the specific compound is not particularly limited, but is preferably from 2,000 to 200,000, more preferably from 5,000 to 100,000, and even more preferably from 10,000 to 50,000.

[0132] (Hydrolysate of specific compounds) The alkoxysilyl group of the specific compound is easily hydrolyzed to form a silanol group (Si-OH). The hydrolyzate of the specific compound may be one in which all of the hydrolyzable groups are hydrolyzed (complete hydrolyzate) or one in which only a portion of the hydrolyzable groups are hydrolyzed (partial hydrolyzate). In other words, the hydrolyzate may be a complete hydrolyzate, a partial hydrolyzate, or a mixture thereof. The silanol group easily condenses with a hydroxy group or the like present on the surface of the inorganic particle to form a bond of --Si--O-- on the surface of the inorganic particle.

[0133] (Hydrolyzed condensation product of specific compound) The hydrolyzate of the specific compound can be a hydrolysis condensation product in which silanol groups undergo dehydration condensation between two molecules to form an -Si-O-Si- bond. Because the specific compound has two or more alkoxysilyl groups, silanol groups remain even in the hydrolysis condensation product of the specific compound, and, like the hydrolysis product of the specific compound, they easily condense with hydroxy groups, etc., on the surface of the inorganic particles to form -Si-O- bonds on the surface of the inorganic particles.

[0134] (Requirement 1: Surface modification with specific compounds, etc.) The above requirement 1 indicates that the inorganic particles are surface-modified with at least one (e.g., a specific compound) selected from the group consisting of a specific compound, a hydrolyzate of a specific compound, and a hydrolysis condensate of a specific compound. In the above requirement 1, the expression "the inorganic particles are surface-modified with a specific compound, etc." means that at least a portion of the surface of the inorganic particles is covered with the specific compound, etc. Preferably, at least a portion of the surface of the inorganic particles is covered with the specific compound, etc. via various bonds, and more preferably, at least a portion of the surface of the inorganic particles is covered via "-Si-O-" bonds. It is believed that the dispersibility of the inorganic particles in the curable composition can be improved by surface-modifying the inorganic particles with the specific compound, etc. Furthermore, since the specific compound is a compound having a polymer chain and two or more alkoxysilyl groups, even a small amount of the specific compound, etc. can sufficiently modify the surface, and therefore it is believed that the dispersibility of the inorganic particles in the curable composition can be improved without impairing the thermal conductivity of the inorganic particles. The surface modification method will be described in detail later.

[0135] In requirement 1, the ratio of the content of the specific compound etc. to the content of the inorganic particles in the curable composition is preferably 0.01 to 10 mass %, more preferably 0.02 to 5 mass %, and even more preferably 0.05 to 3 mass %.

[0136] (Requirement 2: Containment of specific compounds, etc.) The above requirement 2 indicates that the curable composition contains a specific compound, etc. By satisfying requirement 2, when the curable composition is used to form a thermally conductive material, the specific compound, etc. covers the surfaces of the inorganic particles, thereby improving the dispersibility of the inorganic particles in the thermally conductive material.

[0137] In requirement 2, the ratio of the content of the specific compound etc. to the content of the inorganic particles in the curable composition is preferably 0.01 to 10 mass %, more preferably 0.02 to 5 mass %, and even more preferably 0.05 to 3 mass %.

[0138] [Curing accelerator] The curable composition also preferably contains a curing accelerator. The curing accelerator preferably contains at least one selected from the group consisting of compounds represented by formula (P1) and compounds represented by formula (P2), and more preferably contains a compound represented by formula (P3). When optical isomers exist in the compound contained in the curing accelerator, any of the optical isomers may be used. In addition, one type of optical isomer may be used alone, or multiple optical isomers may be used in combination. When one type of optical isomer is mainly used, its optical purity (ee) is preferably 90 or more, more preferably 95 or more. Similarly, in the formulae (P1) to (P3) shown below, when optical isomers exist, any of the optical isomers may be included.

[0139] [ka]

[0140] In formula (P1), L p represents a single bond or a divalent linking group. Examples of the divalent linking group include an ether group (-O-), a carbonyl group (-CO-), an ester group (-COO-), a thioether group (-S-), -SO2-, -NR- (wherein R represents a hydrogen atom or an alkyl group), a divalent aliphatic hydrocarbon group (for example, an alkylene group, a cycloalkylene group, an alkenylene group (-CH=CH-, etc.), an alkynylene group (-C≡C-, etc.)), a divalent aromatic ring group (for example, an arylene group and a heteroarylene group), and a group formed by combining these. The divalent linking group may further have a substituent. Examples of the substituent include the substituents exemplified in the substituent group Y above. The arylene group may be monocyclic or polycyclic, and preferably has 6 to 25 carbon atoms. The arylene group is preferably a phenylene group, a naphthylene group, an anthracenylene group or a binaphthylene group, and more preferably a binaphthylene group. L p As the group, a divalent aliphatic hydrocarbon group or a divalent aromatic ring group is preferred, and an alkylene group or an arylene group is more preferred.

[0141] R p11 ~R p14 each independently represents a phenyl group which may have a substituent. Examples of the substituent include the substituents exemplified in the above-mentioned group Y of substituents, and an alkyl group is preferable, and a linear or branched alkyl group having 1 to 3 carbon atoms is more preferable.

[0142] n p represents 0 or 1. p As the number, 1 is preferred.

[0143] [ka]

[0144] In formula (P2), R p21 ~R p24 each independently represents a phenyl group which may have a substituent. Examples of the substituent include the substituents exemplified in the above-mentioned group Y of substituents, and an alkyl group is preferable, and a linear or branched alkyl group having 1 to 3 carbon atoms is more preferable.

[0145] X - represents an anion. Examples of the anion include hydroxide ion, fluoride ion, chloride ion, bromide ion, iodide ion, hexafluorophosphate ion, tetrafluoroborate ion, tetraphenylborate ion, dicyanamide ion, alkylphosphate ion (e.g., diethylphosphate ion, etc.), hydrogen sulfate ion, dihydrogenphosphate ion, hydrogenphosphate ion, sulfamate ion, perchlorate ion, benzotriazolide anion, and tetratolylborate anion (e.g., tetra-p-tolylborate anion, etc.). The anion is preferably a tetratolylborate anion.

[0146] [ka]

[0147] In formula (P3), R p31 ~R p34each independently represents a phenyl group which may have a substituent. Examples of the substituent include the substituents exemplified in the above-mentioned group Y of substituents, and an alkyl group is preferable, and a linear or branched alkyl group having 1 to 3 carbon atoms is more preferable.

[0148] The molecular weight of the curing accelerator is often 200 or more, preferably 250 or more, more preferably 400 or more, even more preferably 430 or more, and particularly preferably 600 or more. The upper limit is preferably 10,000 or less, more preferably 1,000 or less, and even more preferably 800 or less. When the molecular weight of the curing accelerator is 250 or more, the vaporization of the curing accelerator itself and / or its thermal decomposition products can be more effectively suppressed during high-temperature heat treatment, resulting in better solder heat resistance. Also, when the molecular weight of the curing accelerator is 10,000 or less, it is easy to function as a curing accelerator.

[0149] In order to obtain better effects of the present invention, the curing accelerator preferably contains a compound containing a phosphorus atom, and also preferably contains a phosphonium salt. The curing accelerator may be a compound containing a phosphorus atom or a phosphonium salt itself. When a phosphonium salt is used as the curing accelerator, the storage stability of the semi-cured film formed from the curable composition is also improved. The content of the phosphorus atom-containing compound or phosphonium salt is preferably from 10 to 100 mass %, more preferably from 50 to 100 mass %, and even more preferably from 80 to 100 mass %, based on the total mass of the curing accelerator.

[0150] The curing accelerators may be used alone or in combination of two or more. The content of the curing accelerator is preferably 0.002% by mass or more, more preferably 0.02% by mass or more, and even more preferably 0.07% by mass or more, based on the total solid content of the curable composition, and the upper limit is preferably 5% by mass or less, more preferably 2% by mass or less, and even more preferably 1% by mass or less, based on the total solid content of the curable composition. The content of the curing accelerator is preferably 0.01% by mass or more, more preferably 0.10% by mass or more, and even more preferably 0.55% by mass or more, based on the total amount of epoxy compounds. The upper limit is preferably 40% by mass or less, more preferably 12% by mass or less, even more preferably 10% by mass or less, and particularly preferably 5% by mass or less, based on the total amount of epoxy compounds.

[0151] [Ion scavenger] The curable composition may also include an ion scavenger. The ion scavenger adsorbs ionic impurities in the curable composition or in the thermally conductive material formed using the curable composition, thereby enabling the insulating properties of the thermally conductive material to be maintained better even when the curable composition or the thermally conductive material absorbs moisture. Examples of the ion scavenger include the inorganic ion scavenger and organic ion scavenger as described above. Examples of organic ion scavengers include triazine thiol compounds, triazine amine compounds, benzimidazole compounds, benztriazole compounds, aminotriazole compounds, and bisphenol reducing agents. All or part of the inorganic particles may also function as an ion scavenger.

[0152] The ion scavenger may be used alone or in combination of two or more. When the curable composition contains an ion scavenger, the content of the ion scavenger (inorganic ion scavenger and / or organic ion scavenger) is preferably 0.01 to 10 mass%, more preferably 0.1 to 20 mass%, and even more preferably 0.2 to 10 mass%, based on the total solid content of the curable composition. When the ion scavenger contains an inorganic ion scavenger, part or all of the ion scavenger may simultaneously fall under the category of inorganic substances.

[0153] [Other ingredients] The curable composition may contain other components in addition to the above components. The other ingredients will be described below.

[0154] (acid anhydride) The curable composition may include an acid anhydride. An acid anhydride is a compound having one or more acid anhydride groups (groups represented by —CO—O—CO—). However, the acid anhydride is a compound different from the above-mentioned specific compounds.

[0155] The number of acid anhydride groups in the acid anhydride is 1 or more, preferably 2 or more, and more preferably 3 or more. The upper limit of the number is, for example, 1,000 or less. The molecular weight of the acid anhydride (weight average molecular weight when there is a molecular weight distribution) is preferably at least 100, more preferably at least 2,000, and even more preferably at least 6,000. The upper limit of the molecular weight is preferably at most 100,000, more preferably at most 30,000, and even more preferably at most 17,000. The acid anhydride may be a low molecular weight compound or a high molecular weight compound. Examples of acid anhydrides that are low molecular weight compounds include maleic anhydride, phthalic anhydride, pyromellitic anhydride, and trimellitic anhydride. In the acid anhydride polymer compound, the acid anhydride group may be incorporated into the main chain or may be present in a side chain. For example, when the polymer compound has a repeating unit based on maleic acid, the acid anhydride group contained in the repeating unit is considered to be incorporated into the main chain.

[0156] The acid anhydrides may be used alone or in combination of two or more. The content of the acid anhydride is preferably from 0.01 to 40 mass %, more preferably from 0.1 to 10 mass %, and even more preferably from 0.6 to 5 mass %, based on the total solid content of the curable composition. The content of the acid anhydride is preferably from 0.1 to 100% by mass, more preferably from 1 to 70% by mass, and even more preferably from 5 to 60% by mass, based on the total content of the epoxy compound and the phenol compound.

[0157] [solvent] The curable composition may further comprise a solvent. The solvent is preferably an organic solvent, such as cyclopentanone, cyclohexanone, ethyl acetate, methyl ethyl ketone, dichloromethane, and tetrahydrofuran. When the curable composition contains a solvent, the content of the solvent is preferably an amount that makes the solid content concentration of the curable composition 20 to 90 mass %, more ... The content of the solvent is preferably from 10 to 80 mass %, more preferably from 15 to 70 mass %, and even more preferably from 20 to 50 mass %, based on the total mass of the curable composition.

[0158] <Method for producing curable composition> The curable composition can be produced by a known method, for example, by mixing the components that can be contained in the curable composition described above. When mixing, the components may be mixed all at once or sequentially. Among these, a preferred method for producing a curable composition that satisfies the above requirement 1 will be described below.

[0159] A preferred method for producing a curable composition that satisfies the above requirement 1 includes a production method that includes a step of modifying the surfaces of inorganic particles with the above specific compound or the like (surface modification step). The above-mentioned production method preferably further includes a step of surface-treating inorganic particles to obtain modified inorganic particles (modification step). When the above-mentioned modification step is included, the modification step is preferably carried out before the surface modification step. That is, the surface modification step is preferably carried out on the surface of the above-mentioned modified inorganic particles. Therefore, a preferred method for producing a curable composition that satisfies requirement 1 is a method of mixing the surface-modified inorganic particles with the other components that can be contained in the curable composition described above. Each step will be described below.

[0160] [Denaturation process] The modification step is a step of surface-treating inorganic particles to obtain modified inorganic particles. The modification step is not particularly limited, and examples thereof include the above-mentioned surface treatments. Among them, a step of performing a treatment to oxidize the surfaces of inorganic particles is preferred, and a step of contacting inorganic particles with an oxidizing agent in an aqueous solution to obtain modified inorganic particles is more preferred.

[0161] The inorganic particles to be subjected to the modification step are preferably boron nitride particles or aggregates thereof, more preferably aggregates of boron nitride particles. Therefore, the resulting modified inorganic particles are preferably modified boron nitride particles or particles obtained by modifying aggregates of boron nitride particles, more preferably particles obtained by modifying aggregates of boron nitride particles.

[0162] The aqueous solution is preferably an alkaline aqueous solution. The pH of the alkaline aqueous solution is often 8 or higher, preferably 12 or higher, more preferably greater than 12, even more preferably 13 or higher, and particularly preferably greater than 13. The upper limit is preferably 14 or lower. The pH of the aqueous solution refers to the pH of the aqueous solution in a state in which the aqueous solution contains inorganic particles and the oxidizing agent. In other words, the aqueous solution contains an alkaline compound, water, inorganic particles, and an oxidizing agent as necessary.

[0163] The time for which the inorganic particles are brought into contact with the oxidizing agent in the aqueous solution is preferably from 0.1 to 24 hours, more preferably from 0.5 to 10 hours, and even more preferably from 1.5 to 6 hours. The temperature of the aqueous solution when the inorganic particles and the oxidizing agent are brought into contact with each other is preferably 1 to 95°C, more preferably 25 to 80°C, and even more preferably 45 to 65°C.

[0164] As a method for contacting the inorganic particles with the oxidizing agent in the aqueous solution, for example, a method for contacting them in a mixed liquid can be mentioned. Specifically, the inorganic particles, the specific compound, etc. are brought into contact with each other in a mixed liquid containing water and / or an organic solvent.

[0165] Examples of organic solvents include methanol, ethanol, 2-propanol, acetonitrile, cyclopentanone, cyclohexanone, ethyl acetate, methyl ethyl ketone, dichloromethane, and tetrahydrofuran. The organic solvent may be used alone or in combination of two or more kinds.

[0166] Examples of methods for contacting the inorganic particles with the oxidizing agent include a method in which the inorganic particles and the oxidizing agent are contacted while being stirred using a mechanical stirrer such as a Three-One Motor or a magnetic stirrer, and a method in which the inorganic particles are contacted while being circulated in a cartridge filled with the inorganic particles using a pump or the like.

[0167] It is preferable that after the inorganic particles are brought into contact with the oxidizing agent in the aqueous solution, the resulting modified inorganic particles are taken out from the aqueous solution. The modified inorganic particles can be extracted from the aqueous solution by, for example, filtering the aqueous solution and separating out the modified inorganic particles as a residue. It is also preferable to wash the extracted modified inorganic particles with water and / or an organic solvent, etc. It is also preferable to dry the washed inorganic particles in an oven, etc.

[0168] The content of water in the aqueous solution is preferably 20 to 99% by mass, more preferably 50 to 95% by mass, and even more preferably 65 to 90% by mass, based on the total mass of the aqueous solution.

[0169] (oxidizing agent) Examples of oxidizing agents used in the modification step include persulfates such as sodium persulfate, potassium persulfate, and ammonium persulfate; nitrates such as cerium ammonium nitrate, sodium nitrate, and ammonium nitrate; peroxides such as hydrogen peroxide and tert-butyl hydroperoxide; transition metal compounds such as divalent copper compounds and manganese compounds; hypervalent iodine compounds such as potassium periodate and sodium periodate; quinone compounds such as benzoquinone, naphthoquinone, anthraquinone, and chloranil; and salts of halogen oxoacids such as sodium hypochlorite and sodium chlorite. Preferably, the oxidizing agent comprises a persulfate, and more preferably is a persulfate. In addition, a catalyst may be used in addition to the oxidizing agent to assist the action of the oxidizing agent. Examples of the catalyst include divalent iron compounds (e.g., FeSO4) and trivalent iron compounds. The oxidizing agent and / or catalyst may be a hydrate.

[0170] The standard oxidation-reduction potential of the oxidizing agent is preferably 0.30 V or higher, more preferably 1.50 V or higher, and even more preferably 1.70 V or higher. The upper limit is preferably 4.00 V or lower, more preferably 2.50 V or lower. The standard oxidation-reduction potential is a value based on the standard hydrogen electrode.

[0171] The oxidizing agents may be used alone or in combination of two or more. The content of the oxidizing agent in the aqueous solution is preferably 0.05 to 20 parts by mass, more preferably 0.1 to 20 parts by mass, and even more preferably 1 to 20 parts by mass, relative to 100 parts by mass of water in the aqueous solution.

[0172] The catalyst may be used alone or in combination of two or more. When the aqueous solution contains a catalyst, the content of the catalyst is preferably 0.005 to 2 parts by mass, more preferably 0.01 to 2 parts by mass, and even more preferably 0.1 to 2 parts by mass, per 100 parts by mass of water in the aqueous solution.

[0173] (alkali compounds) The aqueous solution preferably contains an alkaline compound in addition to the above components in order to adjust the pH of the aqueous solution. Examples of the alkaline compound include inorganic bases such as alkali metal hydroxides (for example, sodium hydroxide, etc.) and alkaline earth metal hydroxides; and organic bases. The content of the alkaline compound in the aqueous solution may be an amount that appropriately adjusts the pH of the aqueous solution to a desired value, and may be, for example, 0.1 to 10 parts by mass per 100 parts by mass of water in the aqueous solution.

[0174] [Surface modification process] The surface modification step is a step of modifying the surfaces of inorganic particles with the above-mentioned specific compound or the like. In the surface modification step, it is preferable to bring inorganic particles into contact with a specific compound, etc. The method for bringing inorganic particles into contact with the specific compound, etc. may be the same as that in the modification step. The solution used when bringing inorganic particles into contact with the specific compound, etc. may contain a surface modifier other than the specific compound, etc. (for example, a silane coupling agent and a metal coupling agent). The specific compound to be brought into contact with the inorganic particles is preferably a hydrolysate of the specific compound or a hydrolysis condensate of the specific compound. That is, the specific compound is preferably subjected to a hydrolysis treatment before being brought into contact with the inorganic particles.

[0175] (hydrolysis treatment) The hydrolysis treatment is a treatment for hydrolyzing the specific compound. By the hydrolysis treatment, the alkoxysilyl groups of the specific compound are hydrolyzed to generate silanol groups, which can form bonds with the surfaces of the inorganic particles.

[0176] The hydrolysis method is not particularly limited as long as the conditions are such that the alkoxy group is hydrolyzed. Specifically, it is preferable to use an acidic solution (for example, an aqueous solution of hydrochloric acid and acetic acid, etc.) The acidic solution may contain an organic solvent.

[0177] The method for mixing the components that can be contained in the curable composition is not particularly limited, and known methods can be used. The mixing device used for mixing is preferably a submerged disperser, and examples include agitators such as a planetary centrifugal mixer and a high-speed rotary shear type agitator, a colloid mill, a roll mill, a high-pressure injection type disperser, an ultrasonic disperser, a bead mill, and a homogenizer. One type of mixing device may be used alone, or two or more types may be used in combination. Degassing treatment may be performed before, after, and / or simultaneously with mixing.

[0178] <Method for curing the curable composition> The curable composition of the present invention is preferably a composition for forming a thermally conductive material. The curable composition of the present invention is cured to obtain a thermally conductive material. The curable composition is preferably cured by a thermal curing reaction. The heating temperature during the thermosetting reaction is not particularly limited and may be appropriately selected within the range of, for example, 50 to 250° C. Furthermore, when carrying out the thermosetting reaction, heat treatments at different temperatures may be carried out multiple times. The curing treatment is preferably carried out on a curable composition in the form of a film or sheet. Specifically, for example, the curable composition may be applied to form a film, and then the curing reaction may be carried out. When performing the curing treatment, it is preferable to apply the curable composition to a substrate to form a coating film and then cure it. In this case, the coating film formed on the substrate may be brought into contact with another substrate before the curing treatment. The cured product (thermal conductive material) obtained after curing may or may not be separated from one or both of the substrates. Alternatively, when performing the curing treatment, the curable composition may be applied to separate substrates to form coating films on each substrate, and the curing treatment may be performed while the resulting coating films are in contact with each other. The cured product (thermal conductive material) obtained after curing may or may not be separated from one or both of the substrates.

[0179] The curing treatment may be terminated when the curable composition is in a semi-cured state, or after the curable composition is in a semi-cured state, further curing treatment may be carried out to complete the curing. The curing treatment for bringing the curable composition into a semi-cured state (also referred to as "semi-curing treatment") and the curing treatment for completing the curing (also referred to as "main curing treatment") may be carried out in separate steps.

[0180] For example, in the semi-curing treatment, a curable composition is applied to a substrate to form a coating film, and the coating film on the substrate may then be heated without pressure to form a semi-cured thermal conductive material (also referred to as a "semi-cured film" or "semi-cured sheet"). Alternatively, the coating film on the substrate may be heated while also being pressed to form a semi-cured film. When press processing is performed, the press processing may be performed before, after, or during the heating process. Press processing in the semi-curing treatment may make it easier to adjust the film thickness of the resulting semi-cured film and / or reduce the amount of voids in the semi-cured film. The semi-curing treatment may be carried out in a state where coating films formed on different substrates are laminated together, or may be carried out without laminating the coating films together. The semi-curing treatment may be carried out in a state where the coating film formed from the curable composition is further in contact with a material other than the coating film.

[0181] The resulting semi-cured film may be used as a heat conductive material as is, or may be further subjected to a main curing treatment and then used as a completely cured heat conductive material. In the main curing treatment, the semi-cured film may be heated as is without pressure, or may be heated after or while being pressed. In this case, the main curing treatment may be performed in a state where separate semi-cured films are stacked on top of each other, or may be performed without stacking the semi-cured films on top of each other. The main curing treatment may be carried out in a state where the semi-cured film is placed in contact with a device or the like in which it is used. It is also preferable that the main curing treatment adheres the device to the thermally conductive material of the present invention.

[0182] There are no limitations on the press used for press working that may be carried out during the hardening treatment in the semi-hardening treatment and / or the full hardening treatment, and for example, a flat press or a roll press may be used. When using a roll press, for example, it is preferable to sandwich a coated substrate obtained by forming a coating film on a substrate between a pair of opposing rolls, and apply pressure in the film thickness direction of the coated substrate while rotating the pair of rolls to pass the coated substrate. The coated substrate may have a substrate on only one side of the coating film, or may have a substrate on both sides of the coating film. The coated substrate may be passed through the roll press once or multiple times. During the hardening treatment in the semi-hardening treatment and / or the full hardening treatment, either one of the treatment by platen pressing and the treatment by roll pressing may be carried out, or both may be carried out.

[0183] For information on the production of thermally conductive materials, including curing reactions, please also refer to "High Thermal Conductivity Composite Materials" (CMC Publishing, written by Takezawa Yoshitaka).

[0184] The shape of the thermally conductive material is not particularly limited, and it can be molded into various shapes depending on the application. A typical shape of the molded thermally conductive material is, for example, a sheet shape. That is, the thermally conductive material obtained using the curable composition of the present invention is preferably a thermally conductive sheet. Furthermore, the thermal conductivity of the thermally conductive material obtained using the curable composition of the present invention is preferably isotropic rather than anisotropic.

[0185] The thermally conductive material is preferably insulating (electrically insulating), in other words, the curable composition of the present invention is preferably a thermally conductive insulating composition. For example, the volume resistivity of a thermal conductive material at 23°C and 65% relative humidity is 10 10 Ω·cm or more is preferable, and 10 12 Ω·cm or more is preferable, and 10 14 More preferably, the resistivity is 10 Ω·cm or more. 18 Ω·cm or less is preferable.

[0186] <Uses of thermal conductive materials> The thermally conductive material obtained using the curable composition of the present invention can be used as a heat dissipation material such as a heat dissipation sheet, and can be used for heat dissipation purposes in various devices. More specifically, a device with a thermally conductive layer can be produced by disposing a thermally conductive layer containing the thermally conductive material of the present invention on the device, and the heat generated from the device can be efficiently dissipated by the thermally conductive layer. The thermally conductive layer may be a thermally conductive layer containing a thermally conductive multilayer sheet, which will be described later. The thermally conductive material obtained using the curable composition of the present invention has sufficient thermal conductivity and high heat resistance, and is therefore suitable for heat dissipation applications in power semiconductor devices used in various electrical equipment such as personal computers, general home appliances, and automobiles. Furthermore, since the thermally conductive material obtained using the curable composition of the present invention has sufficient thermal conductivity even in a semi-cured state, it can be used as a heat dissipation material to be placed in areas where it is difficult for light for photocuring to reach, such as gaps between components of various devices.In addition, since it has excellent adhesive properties, it can also be used as a thermally conductive adhesive.

[0187] The thermally conductive material obtained using the curable composition of the present invention may be used in combination with a component other than a component formed from the curable composition. For example, a thermally conductive material (such as a thermally conductive sheet) may be combined with a support (adherend) other than the layer formed from the curable composition. Examples of the support (adherend) include plastic materials, metal materials, and glass. Examples of the plastic materials include polyesters such as polyethylene terephthalate (PET), polycarbonate, acrylic resins, epoxy resins, polyurethanes, polyamides, polyolefins, cellulose derivatives, and silicones. Examples of the metal materials include copper and aluminum. The support (adherend) is also preferably in the form of a sheet. The thickness of the sheet-like thermally conductive material (thermally conductive sheet) is preferably 100 to 300 μm, more preferably 150 to 250 μm.

[0188] Furthermore, an adhesive layer and / or a pressure-sensitive adhesive layer may be combined with the thermally conductive material (preferably a thermally conductive sheet). By joining the thermally conductive material to an object to which heat should be transferred, such as a device, via such an adhesive layer and / or pressure-sensitive adhesive layer, a stronger bond between the thermally conductive material and the object can be achieved. The thermally conductive material formed from the curable composition of the present invention also has good adhesion to the adhesive layer and pressure-sensitive adhesive layer, and peeling at the interface between the thermally conductive material and the adhesive layer or pressure-sensitive adhesive layer can be suppressed. For example, a thermally conductive multilayer sheet may be produced which has a thermally conductive sheet and an adhesive layer or pressure-sensitive adhesive layer provided on one or both sides of the thermally conductive sheet. One or both sides of the thermally conductive sheet may be provided with either an adhesive layer or a pressure-sensitive adhesive layer, or both. An adhesive layer may be provided on one side of the thermally conductive sheet, and a pressure-sensitive adhesive layer may be provided on the other side. Furthermore, an adhesive layer and / or a pressure-sensitive adhesive layer may be provided partially or entirely on one or both sides of the thermally conductive sheet. As described above, in the present invention, the thermally conductive material such as the thermally conductive sheet may be in a semi-cured state (semi-cured film), and the thermally conductive sheet in the thermally conductive multilayer sheet may be in a semi-cured state. The adhesive layer in the thermally conductive multilayer sheet may be in a cured, semi-cured, or uncured state. [Example]

[0189] The present invention will be described in more detail below with reference to examples. The materials, amounts used, ratios, treatment details, treatment procedures, etc. shown in the following examples can be changed as appropriate without departing from the spirit of the present invention. Therefore, the scope of the present invention should not be construed as being limited by the following examples.

[0190] <Preparation of Curable Composition> The components shown in the table below were mixed to obtain a curable composition. More specifically, in Example 1, cyclopentanone, a phenol compound, an epoxy compound, a maleimide compound, and a curing accelerator were mixed in the amounts shown in the table below, in that order, and then the inorganic particles BN1 were added. The resulting mixture was treated for 5 minutes in a planetary centrifugal mixer (THINKY Corporation, Awatori Rentaro ARE-310) to obtain the curable composition used in Example 1. For the other examples and comparative examples, curable compositions were obtained in the same manner. Each component used in preparing the curable composition will be described below.

[0191] [Phenol compounds] The average value of n in A-3 is 1.

[0192] [ka]

[0193] [Epoxy compounds] The weight average molecular weight of B-8 is 3000, and the average value of n of B-9 is 10. * indicates a bonding position.

[0194] [ka]

[0195] [Maleimide compounds] E-1: MIR-3000-70MT, the average value of n for E-1 is 1, manufactured by Nippon Kayaku Co., Ltd. E-2: BMI-70, manufactured by Keiai Kasei Co., Ltd.

[0196] [ka]

[0197] [Curing accelerator] C-1: Tetraphenylphosphonium tetra-p-tolylborate (TPP-MK, manufactured by Hokko Chemical Co., Ltd.) C-2: (S)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl

[0198] [Synthesis of specific compounds] The specific compounds used in Example 1 were synthesized according to the following procedure, where * indicates the bond position.

[0199] [ka] JPEG0007794622000019.jpg3177

[0200] Dipentaerythritol hexakis(3-mercaptopropionate) (Fujifilm Wako Pure Chemical Industries, 14.5 g) and a silane coupling agent (KBE-1003, Shin-Etsu Chemical Co., Ltd., 10.5 g) were dissolved in cyclopentanone (60 mL) to prepare a precursor solution. V-601 (Fujifilm Wako Pure Chemical Industries, 32 mg) was added to the solution, and the mixture was stirred for 2 hours at 80°C under a nitrogen atmosphere. Further V-601 (Fujifilm Wako Pure Chemical Industries, 32 mg) was then added, and the mixture was stirred for 2 hours at 90°C under a nitrogen atmosphere. After confirming the disappearance of the silane coupling agent by NMR, cyclopentanone was added to adjust the concentration, yielding a 30% cyclopentanone solution of the intermediate (the compound in the middle part of the above chemical formula) (intermediate solution). Next, the above intermediate solution (3.0 g), 2-methoxyethyl methacrylate (Tokyo Chemical Industry Co., Ltd., 14.1 g, corresponding to the monomer), and V-601 (Fujifilm Wako Pure Chemical Industries, Ltd., 68 mg) were dissolved in cyclopentanone (16.6 mL) to prepare a reaction solution. The above reaction solution was added dropwise to cyclopentanone (8.4 mL) over 2.5 hours while maintaining the temperature at 80°C under a nitrogen atmosphere. After the addition was completed, the mixture was stirred for 2.5 hours. After that, V-601 (Fujifilm Wako Pure Chemical Industries, Ltd., 68 mg) was added, and the mixture was heated to 90°C and stirred for an additional 2 hours. Using the above procedure, a 35% cyclopentanone solution of the specific compound was obtained. In the above formula, m = 3 for the specific compound used in Example 1, and the average number of alkoxysilyl groups per molecule of the specific compound was 3. The monomer equivalent of the specific compound means the amount of monomer when the intermediate is taken as 1 equivalent, and the monomer equivalent of the specific compound used in Example 1 was 150 equivalents. That is, 150 molecules of monomer were used per molecule of the intermediate. The specific compounds used in each Example and Comparative Example were synthesized using the same procedure. The specific compounds used in each Example and Comparative Example were synthesized using the monomers shown in the table below instead of 2-methoxyethyl methacrylate. When multiple monomers were used, they were mixed in the mass ratios shown in the table below.

[0201] In the tables below, the column for "central structure" for specific compounds shows the structures shown below: In the formulas below, * indicates the bonding position.

[0202] [ka]

[0203] In the tables below, the abbreviations in the columns "Monomer 1," "Monomer 2," and "Monomer 3" for specific compounds represent the structures shown below. When using the monomers represented by "BBEM" and "BPEM" below, the specific compounds were synthesized and then dehalogenated by the action of diazabicycloundecene. That is, when using the monomers represented by "BBEM" and "BPEM," the specific compounds synthesized had a methacryloyl group and an acryloyl group in the polymer chain, respectively.

[0204] [ka] JPEG0007794622000022.jpg84137

[0205] [Inorganic particles] Modified particles X1 to X12 were produced using the following particles X1 to X5 through the following modification step. Note that in the tables below, when there is simply "particle X1," it means that the following particle X1 was used, not the modified particle.

[0206] (Particle X) Particle X1: PTX-60, boron nitride agglomerates, particle size D 50 : 60 μm, manufactured by Momentive Particle X2: HP-40, boron nitride agglomerates, particle size D 50 : 40 μm, manufactured by Mizushima Ferroalloy Co., Ltd. Particle X3: PCTL5MHF, boron nitride agglomerates, particle size D 50 : 80 μm, Saint-Gobain Particle X4: PT-110, flake boron nitride, particle size D 50 : 45μm, Momentive Particle X5: SGPS, boron nitride agglomerates, particle size D 50 : 12 μm, manufactured by Denka Particle X6: AA-3, spherical aluminum oxide, particle size D 50 : 3 μm, manufactured by Sumitomo Chemical Co., Ltd. Particle X7: AA-18, spherical aluminum oxide, particle size D 50 : 18 μm, manufactured by Sumitomo Chemical Co., Ltd.

[0207] (Modified particle X) Modified particles X1: Modified boron nitride produced by the following production method 1 Modified particles X2: Modified boron nitride produced by the production method 2 described below Modified particle X3: Modified boron nitride produced by the manufacturing method 3 shown below Modified particle X4: Modified boron nitride produced by the manufacturing method 4 shown below Modified particle X5: Modified boron nitride produced by the production method 5 shown below Modified particle X6: Modified boron nitride produced by the production method 6 shown below Modified particle X7: Modified boron nitride produced by the production method 7 shown below Modified particle X8: Modified boron nitride produced by the production method 8 shown below Modified particle X9: Modified boron nitride produced by the production method 9 shown below Modified particle X10: Modified boron nitride produced by the production method 10 shown below Modified particle X11: Modified boron nitride produced by the production method 11 shown below Modified particle X12: Modified boron nitride produced by the production method 12 shown below

[0208] -Manufacturing method 1- Boron nitride (particles X1, 50 g) was added to aqueous NaOH (40 g NaOH / 400 mL water) and stirred. Sodium persulfate solution (9.6 g sodium persulfate / 100 mL water) was then added to the NaOH solution, and the NaOH solution was heated to 50°C and stirred for an additional 3 hours (modification step). A Three-One Motor (manufactured by Shinto Scientific Co., Ltd.) was used for stirring at 150 rpm. After the NaOH water was cooled to room temperature, the boron nitride in the NaOH water was filtered off and washed with water (500 mL) and acetonitrile (250 mL) to obtain modified particles X1.

[0209] -Manufacturing method 2- Boron nitride (particles X1, 50 g) was added to water (400 mL) and stirred to obtain a mixed solution. 30% by mass of hydrogen peroxide solution (30 mL) was further added to the mixed solution, and the mixed solution was then heated to 50°C and stirred for an additional 3 hours. Stirring was performed at 150 rpm using a Three-One Motor (manufactured by Shinto Scientific Co., Ltd.). After the mixture was cooled to room temperature, the boron nitride in the mixture was filtered off and washed with water (500 mL) and acetonitrile (250 mL) to obtain modified particles X2.

[0210] -Manufacturing method 3- Modified particles X3 were obtained in the same manner as in Production Method 1, except that the NaOH water in Production Method 1 was changed to (NaOH: 0.02 g / water: 400 mL). In Production Method 3, the pH of the liquid (aqueous solution) obtained by mixing NaOH water (NaOH: 0.02 g / water: 400 mL), boron nitride (50 g), and sodium persulfate water (sodium persulfate: 9.6 g / water: 100 mL) was 11.

[0211] -Manufacturing method 4- Boron nitride (particles X1, 50 g) was heated at 1,000° C. for 1 hour in an oxidizing atmosphere to obtain modified particles X4.

[0212] -Manufacturing method 5- Boron nitride (particles X2, 15 g) was subjected to vacuum plasma treatment (gas type: O2, pressure: 30 Pa, output: 500 W) using a plasma cleaner PDC210 (Yamato Scientific Co., Ltd.). The boron nitride to be treated was stirred every 5 minutes of vacuum plasma treatment, and the vacuum plasma treatment was continued until the total treatment time reached 30 minutes, yielding modified particles X5.

[0213] -Manufacturing method 6- Modified particles X6 were obtained in the same manner as in Production Method 1, except that boron nitride (particles X1, 50 g) was changed to boron nitride (particles X2, 50 g).

[0214] -Manufacturing method 7- Boron nitride (particles X2, 50 g) was added to water (400 mL) and stirred to obtain a mixed solution. Sodium hypochlorite water (sodium hypochlorite pentahydrate: 48 g / water: 100 mL) was further added to the mixed solution, and the mixed solution was then heated to 50°C and stirred for an additional 3 hours. Stirring was performed at 150 rpm using a Three-One Motor (manufactured by Shinto Scientific Co., Ltd.). After the mixture was cooled to room temperature, the boron nitride in the mixture was filtered off and washed with water (500 mL) and acetonitrile (250 mL) to obtain modified particles X7.

[0215] -Manufacturing method 8- Boron nitride (particles X2, 50 g) was heated at 1000° C. for 1 hour to obtain modified particles X8.

[0216] -Manufacturing method 9- Boron nitride (particles X2, 50 g) was heated at 900° C. for 4 hours to obtain modified particles X9.

[0217] -Manufacturing method 10- Modified particles X10 were obtained in the same manner as in Production Method 1, except that boron nitride (particles X1, 50 g) was changed to boron nitride (particles X3, 50 g).

[0218] -Manufacturing method 11- Modified particles X11 were obtained in the same manner as in Production Method 1, except that boron nitride (particles X1, 50 g) was changed to boron nitride (particles X4, 50 g).

[0219] -Manufacturing method 12- Modified particles X12 were obtained in the same manner as in Production Method 1, except that boron nitride (particles X1, 50 g) was changed to boron nitride (particles X5, 50 g).

[0220] (Surface modification with specific compounds) The inorganic particles BN1 used in Example 1 were obtained by the following procedure. Note that the following procedure corresponds to addition method "A" in the table below, and the inorganic particles obtained by the following procedure are inorganic particles that satisfy the above-mentioned requirement 1. Isopropyl alcohol (3.3 g), distilled water (1.2 g), and acetic acid (0.3 g) were added to the cyclopentanone solution of the specific compound (solid content 35% by mass, 4.5 g) obtained by the above procedure, and the mixture was stirred at room temperature for 1 hour to obtain a hydrolyzed solution of the specific compound. Next, the modified particles X1 (200 g) were added to acetonitrile (400 mL), and the hydrolysis solution of the specific compound was added and stirred for 1 hour. The boron nitride in the acetonitrile was filtered, washed with acetonitrile (40 mL), and dried in an oven at 40 °C to obtain inorganic particles BN1. In Example 1, the inorganic particles BN1 obtained by the above procedure were added in the amount shown in the table relative to the total solid content of the curable composition to prepare a curable composition.

[0221] The inorganic particles used in other examples were obtained by the same procedure as those corresponding to addition method "A" in the tables below. That is, the notation "BN2" or the like in the "Type" column of inorganic particles indicates that inorganic particles obtained according to the above method were used in combination with the particles and specific compounds shown in the tables below. The type of inorganic particles used in Example 108, "(BN1 / AL1)," indicates that the curable composition was prepared by adding the inorganic particles BN1 and the inorganic particles AL1 obtained by using particles X6 instead of modified particles X1 in the above method in the amounts shown in the table relative to the total solids of the curable composition. The type of inorganic particles used in Example 109, "(AL2 / AL1)," indicates that the curable composition was prepared by adding the inorganic particles AL2 obtained by using particles X7 instead of modified particles X1 in the above method and the inorganic particles AL1 in the amounts shown in the table relative to the total solids of the curable composition. The inorganic particles (BN45) used in Examples 114 to 117 were surface-modified using the above procedure, but with the specific compound and X-12-967C (3-trimethoxysilylpropylsuccinic anhydride, manufactured by Shin-Etsu Silicones Co., Ltd.) instead of the specific compound, so that the total content was the same as in the above procedure. The mass ratio of the content of X-12-967C to the specific compound was adjusted to 1. The inorganic particles (BN47) used in Comparative Example 2 were surface-modified in the same manner as above, except that KBM-403 (3-glycidoxypropyltrimethoxysilane, manufactured by Shin-Etsu Silicones Co., Ltd.) was used instead of the specific compound. On the other hand, in the tables below, when the column for "addition method" is "B," the curable composition was prepared without the surface modification by separately adding the inorganic particles and the specific compound so that the total solid content was the amount shown in the table. The ratio of the inorganic particles to the specific compound was adjusted to the mass ratio used for the surface modification. The inorganic particles (BN46) used in Comparative Example 1 were not subjected to the above-mentioned surface modification, and no specific compound was added in the preparation of the curable composition.

[0222] The amount of solvent added to each curable composition was set so that the solid content concentration of each curable composition would be 50 to 80% by mass. The solid content concentration of each curable composition was adjusted within the above range for each curable composition so that the viscosity of each curable composition would be approximately the same. The amounts added were adjusted so that the total content of the epoxy compound and the phenolic compound was the amount shown in the "Total Amount (% by mass)" column in the table relative to the total solids content of the curable composition, and the epoxy compound and the phenolic compound were equivalent (the amount in which the number of epoxy groups in the epoxy compound is equal to the number of hydroxyl groups in the phenolic compound). Furthermore, when two compounds are listed in the "Phenol Compound" and "Epoxy Compound" columns (e.g., "B-1 / B-3"), this means that two types of compounds were used, and the numbers in parentheses in each column (e.g., "1 / 1") represent the mass ratio of the two compounds. In the curable composition, the amounts of the maleimide compound, the curing accelerator, and the inorganic particles BN1 to BN47 were adjusted to the amounts (mass %) shown in parentheses in each column of the table, relative to the total solid content of the curable composition.

[0223] <Evaluation> [Preparation of semi-cured sheet (semi-cured film)] Using an applicator with a micrometer, the prepared curable composition was uniformly applied onto the release surface of a release-treated PET film (PET756501, manufactured by Lintec Corporation, film thickness 75 μm), and then dried at 120°C for 4 minutes to produce a semi-cured sheet (semi-cured film).

[0224] [Making a thermal conductive sheet] The surface of the obtained semi-cured sheet opposite the PET film was covered with a release-treated PET film and heat-pressed in air (heat plate temperature 180°C, pressure 20 MPa for 5 minutes). This was then heat-treated at 180°C for 90 minutes under normal pressure to obtain a resin sheet. The PET films on both sides of the resin sheet were peeled off to obtain a thermally conductive sheet (thermal conductive material) with an average thickness of 120 μm.

[0225] [Evaluation of thermal conductivity] (1) The thermal diffusivity of the thermal conductive sheet in the thickness direction was measured using the laser flash method using the NETZSCH LFA467. (2) Using a Mettler-Toledo balance "XS204," the specific gravity of the thermal conductive sheet was measured using the Archimedes method ("Solid Specific Gravity Measurement Kit"). (3) Using a Seiko Instruments DSC320 / 6200, the specific heat of the thermally conductive sheet at 25°C was measured under a temperature increase rate of 10°C / min. (4) The thermal conductivity of the thermal conductive sheet was calculated by multiplying the obtained thermal diffusivity by the specific gravity and specific heat. The thermal conductivity of the thermally conductive sheet was classified according to the following criteria, and the thermal conductivity of the thermally conductive sheet obtained using the curable composition of each Example or Comparative Example was evaluated. A: 18W / mK or more B: 15W / mK or more and less than 18W / mK C: 12W / mK or more and less than 15W / mK D: Less than 12W / mK

[0226] [Copper foil peel strength (adhesion)] The PET film was peeled off from the resulting semi-cured sheet, and the resulting semi-cured sheet was cut into 20 mm × 60 mm strips and sandwiched between an adherend: electrolytic copper foil (20 mm × 100 mm, 35 μm thick) and an aluminum plate (30 mm × 60 mm, 1 mm thick). The resulting laminate was heat-pressed in air (heat plate temperature 180°C, pressure 20 MPa for 5 minutes, followed by heat plate temperature 180°C, normal pressure for 90 minutes) to obtain an aluminum base substrate with copper foil in which the thermally conductive sheet and adherend were integrated. The copper foil peel strength of the obtained copper foil-attached aluminum base substrate was measured using a digital force gauge (ZTS-200N, manufactured by Imada Co., Ltd.) and a 90° peel test jig (P90-200N-BB, manufactured by Imada Co., Ltd.) according to the method for measuring peel strength under normal conditions described in JIS C 6481. In the peel strength test, the copper foil was peeled at an angle of 90° to the copper foil-attached aluminum base substrate at a peel rate of 50 mm / min. The obtained copper foil peel strength was classified and evaluated according to the following criteria. AA:6N / cm or more A: 5N / cm or more but less than 6N / cm B: 4N / cm or more and less than 5N / cm C: 3N / cm or more and less than 4N / cm D: Less than 3N / cm

[0227] [Evaluation of solder heat resistance] After peeling the PET film from the obtained semi-cured sheet, the sheet was sandwiched between a 2 mm thick copper substrate and 0.15 mm thick copper foil, and then heat-pressed in air (heat plate temperature 180°C, pressure 20 MPa, 5 minutes) to obtain a laminate with a "copper substrate-thermal conductive sheet-copper foil" configuration. The 0.15 mm copper foil in the laminate was etched into a circular shape with a diameter of 2 cm, and the laminate was used as a sample for solder heat resistance testing with a configuration of "copper substrate - thermally conductive sheet - circular copper foil with a diameter of 2 cm." The sample was subjected to a heat treatment of heating at 300°C for 5 minutes and then cooling to room temperature (25°C) 1 to 3 times. After that, a circular copper foil with a diameter of 2 cm was peeled off from the sample that had been heat treated 1 to 3 times. The state of failure of the peeled samples was visually inspected, and if cohesive failure of the thermal conductive sheet occurred over the entire peeled surface, the sample was deemed to have passed. If interfacial peeling occurred over part or the entire surface between the copper substrate and thermal conductive sheet and / or between the thermal conductive sheet and the 2 cm diameter circular copper foil, the sample was deemed to have failed. Based on the relationship between the number of heat treatments and whether the sheet was passed or failed, the solder heat resistance of the thermal conductive sheet was evaluated according to the following classification. A: Passed the heat treatment three times. B: The product passed the heat treatment twice, but failed after three times. C: Passed the heat treatment once, but failed it twice. D: Failed after one heat treatment.

[0228] <Result> The evaluation results are shown in Tables 1-1 to 1-5. In the table, if the column for the specific compound addition method is "A," this indicates that the inorganic particles were surface-modified by the method described above (surface modification with a specific compound), and the above requirement 1 is met. On the other hand, if the column for the addition method is "B," this indicates that the curable composition was prepared by adding the inorganic particles and the specific compound separately, without performing the above surface modification. If the column for the addition method is "B," the above requirement 2 is met. In the table, the "number of branches" in the specific compound column indicates the number of bonds in the central structure of the specific compound, and in the above formula (a), n a +m a Corresponds to. In the table, the "number of alkoxysilyl groups" in the specific compound column indicates the number of alkoxysilyl groups in one molecule of the specific compound, and in the above formula (a), m a Corresponds to.

[0229] [Table 1]

[0230] [Table 2]

[0231] [Table 3]

[0232] [Table 4]

[0233] [Table 5]

[0234] The results in Tables 1-1 to 1-5 confirm that the curable composition of the present invention exhibits the desired effects. Comparison of Examples 16 to 19 with other Examples confirmed that when the specific compound contains a repeating unit having an acid anhydride group or a repeating unit having an aromatic heterocyclic group in the polymer chain, the peel strength is superior. Comparison of Examples 25 and 28 to 30 with Examples 1 and 24 confirmed that when the number of alkoxysilyl groups in the specific compound was 3 or 4, the peel strength was superior. Comparison of Example 42 with Example 1 confirmed that when the inorganic particles were surface-modified with a specific compound, the thermal conductivity and peel strength were superior. Comparison of Examples 42 and 43 with Examples 1 and 42 confirmed that when the inorganic particles were modified inorganic particles, the thermal conductivity and peel strength were superior. From a comparison between Example 107 and Example 1, it was confirmed that when the curable composition contained a maleimide compound, the thermal conductivity and solder heat resistance were superior. Comparison of Examples 53, 64, 75, 86 and 97 with other Examples confirmed that when the epoxy compound has an aromatic ring, one or more of thermal conductivity, peel strength and solder heat resistance are excellent. Comparison of Examples 108 and 109 with Example 1 confirmed that when the inorganic particles were boron nitride particles or aggregates thereof, excellent thermal conductivity was achieved.

Claims

1. A curable composition comprising a curable compound and inorganic particles, the inorganic particles are selected from the group consisting of inorganic nitride particles and inorganic oxide particles; A curable composition that satisfies the following requirement 1 or requirement 2: Requirement 1: The inorganic particles are surface-modified with at least one selected from the group consisting of a compound having a polymer chain and two or more alkoxysilyl groups, a hydrolyzate of the compound, and a hydrolysis condensate of the compound. Requirement 2: The curable composition contains at least one selected from the group consisting of the compound, a hydrolyzate of the compound, and a hydrolysis condensate of the compound. The compound having a polymer chain and two or more alkoxysilyl groups is a compound represented by formula (a). 【Chemistry 1】 In formula (a), Y ａ represents a polymer chain. The polymer chain has a repeating unit having an acid anhydride group or a repeating unit having an aromatic heterocyclic group. In formula (a), L ａ１ and L ａ２ each independently represents a single bond or a divalent linking group. In formula (a), A ａ is n ａ +m ａ The linking group represents a linking group obtained by removing a hydrogen atom from a hydroxy group of a polyol selected from trimethylolpropane, triethanolamine, erythritol, pentaerythritol, xylitol, mannitol, and dipentaerythritol. In formula (a), X ａ represents an alkoxysilyl group. In formula (a), n ａ represents an integer of 1 or more. In formula (a), m ａ represents an integer of 2 or more.

2. A curable composition comprising a curable compound and inorganic particles, the inorganic particles are selected from the group consisting of inorganic nitride particles and inorganic oxide particles; A curable composition that satisfies the following requirement 1 or requirement 2: Requirement 1: The inorganic particles are surface-modified with at least one selected from the group consisting of a compound having a polymer chain and two or more alkoxysilyl groups, a hydrolyzate of the compound, and a hydrolysis condensate of the compound. Requirement 2: The curable composition contains at least one selected from the group consisting of the compound, a hydrolyzate of the compound, and a hydrolysis condensate of the compound. The compound having a polymer chain and two or more alkoxysilyl groups is a compound represented by formula (a). 【Chemistry 2】 In formula (a), Y a represents a polymer chain. In formula (a), L a1 and L a2 each independently represent a single bond or a divalent linking group. In formula (a), A a represents a linking group having a valence of n a +m a , and the linking group represents a group represented by Z-1, a group represented by Z-2, or a group represented by Z-3. In formula (a), X a represents an alkoxysilyl group. In formula (a), n a represents an integer of 1 or more. In formula (a), m a represents an integer of 2 or more. 【Transformation 3】

3. The linking group is a group represented by Z-1, Said m ａ The curable composition according to claim 2 , wherein is 3 or 4.

4. The curable composition according to any one of claims 1 to 3, wherein the polymer chain has a repeating unit having an acid anhydride group or a repeating unit having an aromatic heterocyclic group.

5. The curable composition according to any one of claims 1 to 4, further comprising an epoxy compound.

6. The curable composition according to any one of claims 1 to 5, further comprising a phenolic compound.

7. the curable composition comprises an epoxy compound and a phenolic compound, The curable composition according to any one of claims 1 to 6, wherein the phenol compound has 3 to 7 hydroxyl groups in the molecule.

8. the curable composition comprises an epoxy compound and a phenolic compound, The curable composition according to any one of claims 1 to 7, which satisfies at least one of the following requirements: the epoxy compound has a triazine skeleton; and the phenol compound has a triazine skeleton.

9. A curable composition comprising a curable compound and inorganic particles, the inorganic particles are selected from the group consisting of inorganic nitride particles and inorganic oxide particles; Meet requirement 1 or requirement 2 below, the curable composition comprises an epoxy compound and a phenolic compound, A curable composition that satisfies at least one of the following requirements: the epoxy compound has a triazine skeleton; and the phenol compound has a triazine skeleton. Requirement 1: The inorganic particles are surface-modified with at least one selected from the group consisting of a compound having a polymer chain and two or more alkoxysilyl groups, a hydrolyzate of the compound, and a hydrolysis condensate of the compound. Requirement 2: The curable composition contains at least one selected from the group consisting of the compound, a hydrolyzate of the compound, and a hydrolysis condensate of the compound. The compound having a polymer chain and two or more alkoxysilyl groups is a compound represented by formula (a). 【Chemistry 4】 In formula (a), Y a represents a polymer chain. In formula (a), L a1 and L a2 each independently represent a single bond or a divalent linking group. In formula (a), A a represents a linking group having a valency of n a +m a , which is formed by removing a hydrogen atom from a hydroxy group of a polyol selected from trimethylolpropane, triethanolamine, erythritol, pentaerythritol, xylitol, mannitol, and dipentaerythritol. In formula (a), X a represents an alkoxysilyl group. In formula (a), n a represents an integer of 1 or more. In formula (a), m a represents an integer of 2 or more.

10. The curable composition according to claim 9, wherein the phenol compound has 3 to 7 hydroxyl groups in the molecule.

11. The curable composition according to any one of claims 1 to 10, wherein the polymer chain has a repeating unit represented by the following formula (y): 【Transformation 5】 In formula (y), R ｙ１ , R ｙ２ and R ｙ３ each independently represents a hydrogen atom or a monovalent substituent. In formula (y), L ｙ１ represents a single bond or a divalent linking group. In formula (y), Z ｙ represents a monovalent substituent. In formula (y), R ｙ２ and Z ｙ may be bonded to form a ring.

12. The curable composition according to any one of claims 1 to 11, wherein the polymer chain has a polymerizable group selected from the group consisting of an acryloyl group, a methacryloyl group, an oxiranyl group, and a vinyl group.

13. The curable composition according to any one of claims 1 to 12, wherein the inorganic particles are boron nitride particles or aggregates thereof.

14. The curable composition according to any one of claims 1 to 13, wherein the inorganic particles are aggregates of boron nitride particles.

15. The curable composition according to any one of claims 1 to 14, further comprising a curing accelerator.

16. The curable composition of claim 15, wherein the cure accelerator comprises a phosphorus atom.

17. A thermally conductive material formed by curing the curable composition according to any one of claims 1 to 16.

18. A thermally conductive sheet comprising the thermally conductive material according to claim 17.

19. A device with a thermally conductive layer, comprising: a device; and a thermally conductive layer including the thermally conductive sheet according to claim 18, which is placed in contact with the device.

20. A compound represented by the following formula (a): 【Transformation 6】 In formula (a), Y ａ represents a polymer chain. The polymer chain has a repeating unit having an acid anhydride group or a repeating unit having an aromatic heterocyclic group. In formula (a), L ａ１ and L ａ２ each independently represents a single bond or a divalent linking group. In formula (a), A ａ is n ａ +m ａ The linking group represents a linking group obtained by removing a hydrogen atom from a hydroxy group of a polyol selected from trimethylolpropane, triethanolamine, erythritol, pentaerythritol, xylitol, mannitol, and dipentaerythritol. In formula (a), X ａ represents an alkoxysilyl group. In formula (a), n ａ represents an integer of 1 or more. In formula (a), m ａ represents an integer of 2 or more.

21. A compound represented by the following formula (a): 【Transformation 7】 In formula (a), Y a represents a polymer chain. In formula (a), L a1 and L a2 each independently represent a single bond or a divalent linking group. In formula (a), A a represents a linking group having a valence of n a +m a , and the linking group represents a group represented by Z-1, a group represented by Z-2, or a group represented by Z-3. In formula (a), X a represents an alkoxysilyl group. In formula (a), n a represents an integer of 1 or more. In formula (a), m a represents an integer of 2 or more. 【Transformation 8】

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