JP7183307B2 - COMPOSITION FOR HEAT CONDUCTIVE MATERIAL, HEAT CONDUCTIVE MATERIAL, HEAT CONDUCTIVE SHEET, DEVICE WITH HEAT CONDUCTIVE LAYER - Google Patents

Description

TECHNICAL FIELD The present invention relates to a composition for forming a thermally conductive material, a thermally conductive material, a thermally conductive sheet, and a device with a thermally conductive layer.

2. Description of the Related Art In recent years, power semiconductor devices used in various electrical equipment such as personal computers, general household appliances, and automobiles have rapidly been miniaturized. It is becoming difficult to control the heat generated from high-density power semiconductor devices due to miniaturization.
In order to deal with such problems, thermally conductive materials are used to promote heat dissipation from power semiconductor devices.
For example, in Patent Document 1, "A thermosetting adhesive containing boron nitride particles (A), an epoxy resin (B), and a phenolic resin (C) ... used to dissipate heat through an insulating resin layer ... for heat dissipation A member.(Claim 1)” is disclosed.

JP 2013-89670 A

The present inventors studied the insulating resin layer described in Patent Document 1 and found that there is room for improvement in terms of thermal conductivity.

Accordingly, an object of the present invention is to provide a composition for forming a thermally conductive material that can provide a thermally conductive material having excellent thermal conductivity.
Another object of the present invention is to provide a thermally conductive material, a thermally conductive sheet, and a device with a thermally conductive layer which are formed from the composition for forming a thermally conductive material.

As a result of intensive studies aimed at solving the above problems, the inventors of the present invention have found that the above problems can be solved by the following configuration.

[1]
A composition for forming a thermally conductive material containing a phenolic compound, an epoxy compound, and an inorganic substance,
whether the phenol compound comprises a spirophenol compound having a phenolic hydroxyl group and a spiro structure;
A composition for forming a heat conductive material, wherein the epoxy compound satisfies at least one of an epoxy group and a spiro epoxy compound having a spiro structure.
[2]
The composition for forming a thermally conductive material according to [1], which contains a spirophenol compound.
[3]
The composition for forming a heat conductive material according to [1] or [2], which contains a spirophenol compound, and the spirophenol compound is a compound represented by the general formula (1) described later.
[4]
The composition for forming a thermally conductive material according to any one of [1] to [3], which contains a spirophenol compound, and the spirophenol compound is a compound represented by the general formula (2) described below.
[5]
The composition for forming a heat conductive material according to any one of [1] to [4], wherein the spirophenol compound has a hydroxyl group content of 6.5 mmol/g or more.
[6]
The composition for forming a heat conductive material according to any one of [1] to [5], wherein the spirophenol compound has a molecular weight of 400 or less.
[7]
The composition for forming a thermally conductive material according to any one of [1] to [6], wherein the inorganic substance contains an inorganic nitride.
[8]
The composition for forming a thermally conductive material according to [7], wherein the inorganic nitride contains boron nitride.
[9]
The composition for forming a thermally conductive material according to any one of [1] to [8], further comprising the inorganic surface modifier.
[10]
The composition for forming a heat conductive material according to [9], wherein the surface modifier has a condensed ring skeleton or a triazine skeleton.
[11]
The composition for forming a thermally conductive material according to any one of [1] to [10], further comprising a curing accelerator.
[12]
A thermally conductive material obtained by curing the composition for forming a thermally conductive material according to any one of [1] to [11].
[13]
A thermally conductive sheet made of the thermally conductive material according to [12].
[14]
A device with a thermally conductive layer, comprising: a device; and a thermally conductive layer containing the thermally conductive sheet of [13] disposed on the device.

ADVANTAGE OF THE INVENTION According to this invention, the composition for thermally-conductive-material formation which can give the thermally-conductive material excellent in thermal conductivity can be provided.
Further, according to the present invention, it is possible to provide a thermally conductive material, a thermally conductive sheet, and a device with a thermally conductive layer formed from the composition for forming a thermally conductive material.

Hereinafter, the composition for forming a thermally conductive material, the thermally conductive material, the thermally conductive sheet, and the device with a thermally conductive layer of the present invention will be described in detail.
The description of the constituent elements described below may be made based on representative embodiments of the present invention, but the present invention is not limited to such embodiments.
In this specification, a numerical range represented by "-" means a range including the numerical values before and after "-" as lower and upper limits.
In the present specification, an epoxy group is a functional group also called an oxiranyl group. For example, two adjacent carbon atoms of a saturated hydrocarbon ring group are bonded by an oxo group (--O--) to form an oxirane ring. Epoxy groups also include groups such as Epoxy groups may or may not have substituents (such as methyl groups) where possible.

Moreover, in this specification, the description of "(meth)acryloyl group" means "either one or both of acryloyl group and methacryloyl group". Moreover, the description "(meth)acrylamide group" means "either one or both of an acrylamide group and a methacrylamide group".

In this specification, the acid anhydride group may be a monovalent group or a divalent group. When the acid anhydride group represents a monovalent group, substitution obtained by removing any hydrogen atom from acid anhydrides such as maleic anhydride, phthalic anhydride, pyromellitic anhydride, and trimellitic anhydride groups. Also, when the acid anhydride group represents a divalent group, it is intended to be a group represented by *--CO--O--CO--* (* represents a bonding position).

In this specification, for substituents and the like that do not specify whether they are substituted or unsubstituted, if possible, further substituents (for example, the group of substituents described below Y) may or may not be present. For example, the expression "alkyl group" means a substituted or unsubstituted alkyl group as long as the intended effect is not impaired.
In this specification, expressions such as "may" or "may" may or may not meet the conditions set as "may" or "may". intended to For example, "optionally having a substituent" also includes "optionally having no substituent".
Moreover, in the present specification, the type of substituent, the position of the substituent, and the number of substituents in the case of "optionally having a substituent" are not particularly limited. The number of substituents may be, for example, 1 or 2 or more.
Examples of substituents include monovalent nonmetallic atomic groups excluding hydrogen atoms, which can be selected from the following substituent group Y, for example.
As used herein, the halogen atom includes, for example, a chlorine atom, a fluorine atom, a bromine atom, and an iodine atom.

Substituent group Y:
Halogen atoms (-F, -Br, -Cl, -I, etc.), hydroxyl groups, amino groups, carboxylic acid groups and their conjugate base groups, carboxylic anhydride groups, cyanate ester groups, unsaturated polymerizable groups, epoxy groups, oxetanyl group, aziridinyl group, thiol group, isocyanate group, thioisocyanate group, aldehyde group, alkoxy group, aryloxy group, alkylthio group, arylthio group, alkyldithio group, aryldithio group, N-alkylamino group, N,N-dialkylamino group, N-arylamino group, N,N-diarylamino group, N-alkyl-N-arylamino 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 -aryl acylamino 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-alkyl ureido group, N',N'-dialkyl-N-arylureido group, N'-aryl-N-alkylureido group, N'-aryl-N-arylureido group, N',N'-diaryl-N-alkyl ureido group, N',N'-diaryl-N-arylureido group, N'-alkyl-N'-aryl-N-alkylureido group, N'-alkyl-N'-aryl-N-arylureido group, alkoxy carbonylamino 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-diaryl carbamoyl group, N-alkyl-N-arylcarbamoyl group, alkylsulfinyl group, arylsulfinyl group, alkylsulfonyl group, arylsulfonyl group, sulfo group (—SO ₃ H) 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-arylsulfina moyl group, sulfamoyl group, N-alkylsulfamoyl group, N,N-dialkylsulfamoyl group, N-arylsulfamoyl group, N,N-diarylsulfamoyl group, N-alkyl-N-arylsulfamoyl group famoyl group, N-acylsulfamoyl group and its conjugate base group, N-alkylsulfonylsulfamoyl group (—SO ₂ NHSO ₂ (alkyl)) and its conjugate base group, N-arylsulfonylsulfamoyl group ( —SO ₂ NHSO ₂ (aryl)) and its conjugate base group, N-alkylsulfonylcarbamoyl group (—CONHSO ₂ (alkyl)) and its conjugate base group, N-arylsulfonylcarbamoyl group (—CONHSO ₂ (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 ( —PO ₃ H ₂ ) and its conjugate base group, dialkylphosphono group (—PO ₃ (alkyl) ₂ ), diarylphosphono group (—PO ₃ (aryl) ₂ ), alkylarylphosphono group (—PO ₃ ( alkyl) (aryl)), a monoalkylphosphono group (—PO ₃ H(alkyl)) and its conjugate base group, a monoarylphosphono group (—PO ₃ H(aryl)) and its conjugate base group, a phosphonooxy group ( —OPO ₃ H ₂ ) and its conjugate base group, dialkylphosphonoxy group (—OPO ₃ (alkyl) ₂ ), diarylphosphonoxy group (—OPO ₃ (aryl) ₂ ), alkylarylphosphonoxy group (— OPO ₃ (alkyl)(aryl)), monoalkylphosphonoxy groups (—OPO ₃ H(alkyl)) and their conjugate base groups, monoarylphosphorus a nooxy group (--OPO ₃ H(aryl)) and its conjugate base group, a cyano group, a nitro group, an aryl group, an alkenyl group, an alkynyl group, and an alkyl group;
In addition, these substituents may or may not form a ring by bonding with each other or with a substituting group, if possible.

[Composition]
The composition for forming a thermally conductive material of the present invention (hereinafter also simply referred to as "composition") is a composition containing a phenol compound, an epoxy compound, and an inorganic substance.
Furthermore, the phenol compound contains a spirophenol compound having a phenolic hydroxyl group and a spiro structure,
The epoxy compound satisfies at least one of the conditions of including an epoxy group and a spiro epoxy compound having a spiro structure.
Although the mechanism by which the problems of the present invention are solved by the configuration as described above is not necessarily clear, the present inventors found that the spirophenol compound and/or spiroepoxy compound contained in the composition provides rigidity in the heat conductive material. It is speculated that the introduction of the spiro structure contributes to the improvement of the thermal conductivity of the resulting thermally conductive material.
Also, good insulation (electrical insulation) can be imparted to the thermally conductive material obtained from the composition of the present invention.
Hereinafter, the excellent thermal conductivity and/or insulating properties of the thermally conductive material is also referred to as the excellent effect of the present invention.

The components contained in the composition are described in detail below.

[Spiro compound]
The composition of the present invention comprises a phenol compound and an epoxy compound, wherein the phenol compound comprises a spirophenol compound having a phenolic hydroxyl group and a spiro structure, or the epoxy compound comprises a spiroepoxy compound having an epoxy group and a spiro structure. contains or satisfies at least one of
In other words, the composition of the present invention comprises the phenolic compound and the epoxy compound, and at least one of the phenolic compound and the epoxy compound comprises a spiro compound.
That is, the composition of the present invention contains at least one of a spirophenol compound and a spiroepoxy compound.
The composition of the present invention preferably contains at least a spirophenol compound because the effect of the present invention is more excellent.

A spiro compound is a compound having a structure in which two rings share only one atom (preferably a carbon atom).
A single atom shared by two rings is also called a spiro atom.
In the present invention, the spiro compound (spirophenol compound and/or spiroepoxy compound) preferably has a group represented by the following general formula (S1), from the viewpoint that the effects of the present invention are more excellent.

In general formula (S1), * represents a binding position.
E ^S , F ^S , G ^S , and H ^S are each independently —O—, —S—, or a group in which the atom directly bonded to I ^S is a carbon atom (—CH ₂ —, or aromatic hydrocarbon group, etc.).
Among them, E ^{2 S} and H 2 ^S are preferably —O— or groups in which the atom directly bonded to I ^{2 S} is a carbon atom.
F ^S and G ^S are preferably groups in which the atom directly bonded to I ^S is a carbon atom.
^IS represents a carbon atom that is a spiro atom.
In the spiro compound having a group represented by general formula (S1), the ring having FS ^{and GS} and the ring having ^FS and ^HS share ^IS as a spiro atom. .

[Phenolic compound]
The compositions of the invention contain a phenolic compound. A phenolic compound is a compound having at least one (preferably 2 to 10, more preferably 2 to 4, still more preferably 4) phenolic hydroxyl groups.
The phenolic compound preferably has no epoxy groups.

<Spirophenol compound>
Phenolic compounds may include spirophenol compounds.
In particular, if the epoxy compound does not contain a spiroepoxy compound, the phenolic compound necessarily contains a spirophenol compound.
When the phenol compound contains a spirophenol compound, the content of the spirophenol compound is preferably 5% by mass or more, more preferably 20% by mass or more, still more preferably 50% by mass or more, and 85% by mass of the total phenolic compound. % or more is particularly preferred. The upper limit is 100% by mass.
A spirophenol compound may be used individually by 1 type, and may use 2 or more types.

The spirophenol compound is a spiro compound and is a compound having one or more (preferably 2 to 10, more preferably 2 to 4, still more preferably 4) phenolic hydroxyl groups.

(general formula (SP))
The spirophenol compound is preferably a compound represented by the general formula (SP) from the viewpoint that the effects of the present invention are more excellent.

In general formula (SP), C represents a carbon atom which is a spiro atom.
In general formula (SP), X ^SP and Y ^SP each independently represent a divalent linking group having one or more phenolic hydroxyl groups.
Both ends of ^XSP are bonded to the same carbon atom C, respectively. Both ends of ^YSP are bonded to the same carbon atom C, respectively. In addition, the carbon atom C to which X ^SP is bonded at both ends and the carbon atom C to which Y ^SP is bonded at both ends are the same, and the compound represented by the general formula (SP) has the above carbon atom C as a spiro It is a spiro compound with atoms.

X ^SP and Y ^SP are each independently preferably a group represented by general formula (S2P).
-CR ^S1 R ^S2 -L ^S1 -L ^S2P -L ^S3 - (S2P)
The group represented by general formula (S2P) in X ^SP and the group represented by general formula (S2P) in Y ^SP may be the same or different.

In general formula (S2P), R ^S1 and R ^S2 each independently represent a hydrogen atom or a substituent.
Among them, R ^S1 and R ^S2 are preferably hydrogen atoms.

In general formula (S2P), L ^S1 represents -CR ^S3 R ^S4 -, -O-, or -S-.
R ^S3 and R ^S4 each independently represent a hydrogen atom or a substituent.
The substituents of R ^S3 and R ^S4 are each independently preferably an alkyl group or an aryl group.
The above alkyl groups may be linear or branched. The number of carbon atoms in the alkyl group is preferably 1-6.
The aryl group may be monocyclic or polycyclic. The number of carbon atoms in the aryl group is preferably 6 to 15, more preferably 6.
Among them, L ^S1 is preferably -CR ^S3 R ^S4 -, more preferably -C(CH ₃ ) ₂ -.

In general formula (S2P), L ^S2P represents a divalent linking group having a phenolic hydroxyl group.
L ^S2P is preferably an aromatic ring group having a phenolic hydroxyl group as a substituent, or -CR ^S5P R ^S6P -.

The aromatic ring group in the aromatic ring group having a phenolic hydroxyl group as a substituent may be monocyclic or polycyclic. The aromatic ring group may be either an aromatic hydrocarbon group or an aromatic heterocyclic group. The number of carbon atoms in the aromatic ring group is preferably 6 to 15, more preferably 6.
The number of phenolic hydroxyl groups that the aromatic ring group has as a substituent is 1 or more, preferably 1 to 5, more preferably 1 to 2. The aromatic ring group may have a substituent (preferably an alkyl group having 1 to 3 carbon atoms) in addition to the hydroxyl group (phenolic hydroxyl group).
The aromatic ring group having a phenolic hydroxyl group as a substituent is preferably a benzene ring group having one or two hydroxyl groups as a substituent, and 1,2-benzenediyl having one or two hydroxyl groups as a substituent. groups are more preferred.

R ^S5P in -CR ^S5P R ^S6P - represents a hydrogen atom or a substituent.
R ^S6P in -CR ^S5P R ^S6P - represents an aryl group having a hydroxyl group as a substituent.
The aryl group in the aryl group having a hydroxyl group as a substituent may be monocyclic or polycyclic. The number of carbon atoms in the aryl group is preferably 6 to 15, more preferably 6.
In the aryl group having a hydroxyl group as a substituent, the number of hydroxyl groups as substituents is 1 or more, preferably 1 to 5, more preferably 1 to 2. The aryl group in the aryl group having a hydroxyl group as a substituent may have a substituent other than a hydroxyl group (phenolic hydroxyl group).
The aryl group having a hydroxyl group as a substituent is preferably a hydroxyphenyl group, more preferably a 4-hydroxyphenyl group.

Among them, L ^S2P is preferably an aromatic ring group having a phenolic hydroxyl group as a substituent, more preferably a benzene ring group having one or two hydroxyl groups as a substituent, and one or two hydroxyl groups as a substituent. A 1,2-benzenediyl group having such a group is more preferable.

In general formula (S2P), L ^S3 represents a single bond, an alkylene group, -O-, or -S-.
The above alkylene group may be linear or branched, preferably linear.
The alkylene group preferably has 1 to 6 carbon atoms, more preferably 1 to 3 carbon atoms.
The alkylene group is preferably -C(CH ₃ ) ₂ - or -CH ₂ -CH ₂ -.
Among them, L ^S3 is preferably -O-.

(general formula (1))
The spirophenol compound is more preferably a compound represented by the general formula (1) because the effects of the present invention are more excellent.

In general formula (1), ns1 and ns2 each independently represent an integer of 1-4.
ns1 and ns2 are each independently preferably 1 to 2, more preferably 2.

In general formula (1), A ^S and D ^S each independently represent -CR ^Sx R ^Sy -, -O-, or -S-.
R ^Sx and R ^Sy each independently represent a hydrogen atom or a substituent.
The substituents of R ^Sx and R ^Sy are each independently preferably an alkyl group or an aryl group.
The above alkyl groups may be linear or branched. The number of carbon atoms in the alkyl group is preferably 1-6.
The aryl group may be monocyclic or polycyclic. The number of carbon atoms in the aryl group is preferably 6 to 15, more preferably 6. Examples of the substituent that the aryl group may have include a hydroxyl group.

In general formula (1), R ^SA , R ^SB , R ^SC and R ^SD each independently represent a hydrogen atom, an alkyl group or an aryl group.
The above alkyl groups may be linear or branched. The number of carbon atoms in the alkyl group is preferably 1-6.
The aryl group may be monocyclic or polycyclic. The number of carbon atoms in the aryl group is preferably 6 to 15, more preferably 6. Examples of the substituent that the aryl group may have include a hydroxyl group.

(general formula (2))
The spirophenol compound is more preferably a compound represented by the general formula (2) because the effect of the present invention is more excellent.

ns1, ns2, R ^SA , R ^SB , R ^SC and R ^SD in general formula (2) are ns1, ns2, R ^SA , R ^SB , R ^SC and R in general formula (1) Similar to ^SD .

The lower limit of the molecular weight of the spirophenol compound is preferably 200 or more, preferably 300 or more, and more preferably 350 or more, from the viewpoint that the effects of the present invention are more excellent. The upper limit is preferably 600 or less, more preferably 400 or less.

From the viewpoint that the effect of the present invention is more excellent, the lower limit of the hydroxyl group content (preferably phenolic hydroxyl group content) of the spirophenol compound is preferably 4.0 mmol/g or more, more preferably 6.5 mmol/g or more. 0 mmol/g or more is more preferable. The upper limit is preferably 25.0 mmol/g or less, more preferably 11.5 mmol/g or less.
In addition, the said hydroxyl group content intends the number of the hydroxyl groups (preferably phenolic hydroxyl groups) which 1g of phenol compounds have.
Moreover, the spirophenol compound may have an active hydrogen-containing group (such as a carboxylic acid group) capable of undergoing a polymerization reaction with an epoxy group, in addition to the hydroxyl group. The lower limit of the content of active hydrogen in the phenol compound (the total content of hydrogen atoms in hydroxyl groups, carboxylic acid groups, etc.) is preferably 4.0 mmol/g or more, more preferably 6.5 mmol/g or more, and 8.0 mmol/g. g or more is more preferable. The upper limit is preferably 25.0 mmol/g or less, more preferably 11.5 mmol/g or less.

<Other phenol compounds>
Phenolic compounds may include other phenolic compounds other than spirophenol compounds.

(general formula (P1))
As other phenol compounds, compounds represented by the general formula (P1) are preferable because the effects of the present invention are more excellent.

In general formula (P1), m1 represents an integer of 0 or more.
m1 is preferably 0 to 10, more preferably 0 to 3, still more preferably 0 or 1, and particularly preferably 1.

In general formula (P1), na and nc each independently represent an integer of 1 or more.
na and nc are each independently preferably 1-4.

In general formula (P1), R ¹ and R ⁶ each independently represent a hydrogen atom, a halogen atom, a carboxylic acid group, a boronic acid group, an aldehyde group, an alkyl group, an alkoxy group, or an alkoxycarbonyl group.
The above alkyl groups may be linear or branched. The number of carbon atoms in the alkyl group is preferably 1-10. The alkyl group may or may not have a substituent.
The alkyl group portion of the alkoxy group and the alkyl group portion of the alkoxycarbonyl group are the same as the alkyl group.
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 still more preferably a hydrogen atom.

In general formula (P1), ^R7 represents a hydrogen atom or a hydroxyl group.
When multiple R ⁷ are present, the multiple R ⁷ may be the same or different.
When a plurality of R ⁷ are present, it is also preferred that at least one R ⁷ among the plurality of R ⁷ present represents a hydroxyl group.

In general formula (P1), L ^x1 represents a single bond, —C(R ² )(R ³ )—, or —CO—, and —C(R ² )(R ³ )— or —CO— is preferable.
L ^x2 represents a single bond, -C(R ⁴ )(R ⁵ )- or -CO-, preferably -C(R ⁴ )(R ⁵ )- or -CO-.
R ² to R ⁵ each independently represent a hydrogen atom or a substituent.
The above substituents are each independently preferably a hydroxyl group, a phenyl group, a halogen atom, a carboxylic acid group, a boronic acid group, an aldehyde group, an alkyl group, an alkoxy group, or an alkoxycarbonyl group, and a hydroxyl group, a halogen atom, or a carboxylic acid group. , a boronic acid group, an aldehyde group, an alkyl group, an alkoxy group, or an alkoxycarbonyl group are more preferred.
The above alkyl groups may be linear or branched. The number of carbon atoms in the alkyl group is preferably 1-10. The alkyl group may or may not have a substituent.
The alkyl group portion of the alkoxy group and the alkyl group portion of the alkoxycarbonyl group are the same as the alkyl group.
The phenyl group may or may not have a substituent, and when it has a substituent, it preferably has 1 to 3 hydroxyl groups.
R ² to R ⁵ are each independently preferably a hydrogen atom or a hydroxyl group, more preferably a hydrogen atom.
L ^x1 and L ^x2 are each independently preferably -CH ₂ -, -CH(OH)-, -CO- or -CH(Ph)-.
Ph above represents a phenyl group which may have a substituent.
In general formula (P1), when a plurality of R ⁴ are present, the plurality of R ⁴ may be the same or different. When there are multiple R ⁵ 's, the multiple R ⁵ 's may be the same or different.

In general formula (P1), Ar ¹ and Ar ² each independently represent a benzene ring group or a naphthalene ring group.
Ar ¹ and Ar ² are each independently preferably a benzene ring group.

In general formula (P1), ^Qa represents a hydrogen atom, an alkyl group, a phenyl group, a halogen atom, a carboxylic acid group, a boronic acid group, an aldehyde group, an alkoxy group, or an alkoxycarbonyl group.
The above alkyl groups may be linear or branched. The number of carbon atoms in the alkyl group is preferably 1-10. The alkyl group may or may not have a substituent.
The alkyl group portion of the alkoxy group and the alkyl group portion of the alkoxycarbonyl group are the same as the alkyl group.
The phenyl group may or may not have a substituent.
Q ^a is preferably bonded at the para-position with respect to the hydroxyl group which the benzene ring group to which Q ^a is bonded may have.
^Qa is preferably a hydrogen atom or an alkyl group. The above alkyl group is preferably a methyl group.

In general formula (P1), when a plurality of R ⁷ , L ^x2 and/or Q ^a are present, the plurality of R ⁷ , L ^x2 and/or Q ^a may be the same or different. good too.

Other phenolic compounds include, for example, benzenepolyols such as benzenetriol, biphenylaralkyl-type phenolic resins, phenolic novolac resins, cresol novolak resins, aromatic hydrocarbon-formaldehyde resin-modified phenolic resins, dicyclopentadiene phenol addition type Resins, phenol aralkyl resins, polyhydric phenol novolac resins synthesized from polyhydric hydroxy compounds and formaldehyde, naphthol aralkyl resins, trimethylolmethane resins, tetraphenylolethane resins, naphthol novolak resins, naphthol phenol cocondensation novolac resins, naphthol Cresol cocondensed novolak resin, biphenyl-modified phenol resin, biphenyl-modified naphthol resin, aminotriazine-modified phenol resin, or alkoxy group-containing aromatic ring-modified novolac resin is also preferred.

The lower limit of the hydroxyl group content (preferably phenolic hydroxyl group content) of other phenol compounds is preferably 3.0 mmol/g or more, more preferably 7.0 mmol/g or more.
The upper limit is preferably 25.0 mmol/g or less, more preferably 20.0 mmol/g or less.
Moreover, other phenol compounds may have an active hydrogen-containing group (such as a carboxylic acid group) capable of undergoing a polymerization reaction with an epoxy group, in addition to the hydroxyl group. The lower limit of the content of active hydrogen in the phenol compound (the total content of hydrogen atoms in hydroxyl groups, carboxylic acid groups, etc.) is preferably 3.0 mmol/g or more, more preferably 7.0 mmol/g or more. The upper limit is preferably 25.0 mmol/g or less, more preferably 20.0 mmol/g or less.

The upper limit of the molecular weight of other phenol compounds is preferably 600 or less, more preferably 500 or less, still more preferably 450 or less, and particularly preferably 400 or less. 110 or more are preferable and, as for a lower limit, 300 or more are more preferable.

Other phenol compounds may be used singly or in combination of two or more.

The composition of the present invention may contain a compound having a group capable of reacting with an epoxy group (also referred to as "another active hydrogen-containing compound") as a compound other than the phenol compound.
When the composition of the present invention contains other active hydrogen-containing compounds, the mass ratio of the content of other active hydrogen-containing compounds to the content of all phenolic compounds in the composition of the present invention (other active hydrogen The content of contained compounds/content of all phenolic compounds) is preferably 0 to 1, more preferably 0 to 0.1, and even more preferably 0 to 0.05.

[Epoxy compound]
The composition of the invention contains an epoxy compound. Epoxy compounds are compounds having at least one (preferably two or more, more preferably 2 to 10) phenolic hydroxyl groups.

<Spiro epoxy compound>
Epoxy compounds may include spiroepoxy compounds.
In particular, if the phenolic compound does not contain a spirophenolic compound, the epoxy compound necessarily contains a spiroepoxy compound.
When the epoxy compound contains a spiroepoxy compound, the content of the spiroepoxy compound is preferably 5% by mass or more, more preferably 20% by mass or more, still more preferably 50% by mass or more, and 85% by mass, based on the total epoxy compound. % or more is particularly preferred. The upper limit is 100% by mass.
A spiro epoxy compound may be used individually by 1 type, and may use 2 or more types.

(general formula (SE))
The spiroepoxy compound is preferably a compound represented by the general formula (SE) from the viewpoint that the effects of the present invention are more excellent.

In general formula (SE), C represents a carbon atom which is a spiro atom.
In general formula (SE), X ^SE and Y ^SE each independently represent a divalent linking group having one or more epoxy groups.
Both ends of X ^SE are bonded to the same carbon atom C, respectively. Both ends of ^YSE are bonded to the same carbon atom C, respectively. Further, the carbon atom C to which X ^SE is bonded at both ends and the carbon atom C to which Y ^SE is bonded at both ends are the same, and the compound represented by the general formula (SE) has the above carbon atom C as a spiro It is a spiro compound with atoms.

X ^SE and Y ^SE are each independently preferably a group represented by general formula (S2E).
-CR ^S1 R ^S2 -L ^S1 -L ^S2E -L ^S3 - (S2E)
The group represented by general formula (S2E) in X ^SE and the group represented by general formula (S2E) in Y ^SE may be the same or different.
R ^S1 , R ^S2 , L ^S1 and L ^S3 in general formula (S2E) are the same as R ^S1 , R ^S2 , L ^S1 and L ^S3 in general formula (S2P) above. be.

In general formula (S2E), L ^S2E represents a divalent linking group having an epoxy group.
L ^S2E is preferably an aromatic ring group having an epoxy group-containing group as a substituent, or -CR ^S5E R ^S6E -.

The aromatic ring group in the aromatic ring group having an epoxy group-containing group as a substituent may be monocyclic or polycyclic. The aromatic ring group may be either an aromatic hydrocarbon group or an aromatic heterocyclic group. The number of carbon atoms in the aromatic ring group is preferably 6 to 15, more preferably 6.
The number of epoxy group-containing groups that the aromatic ring group has as a substituent is 1 or more, preferably 1 to 5, more preferably 1 to 2. The aromatic ring group may have a substituent (preferably an alkyl group having 1 to 3 carbon atoms) in addition to the epoxy group-containing group.
The aromatic ring group having an epoxy group-containing group as a substituent is preferably a benzene ring group having one or two epoxy group-containing groups as a substituent, and one or two epoxy group-containing groups as a substituent. A 1,2-benzenediyl group having a

The epoxy group-containing group is not limited as long as it is a group having an epoxy group, and may be the epoxy group itself.
Moreover, the epoxy group may have a substituent. As the substituent which the epoxy group may have, a linear or branched alkyl group having 1 to 6 carbon atoms is preferable.
The epoxy group-containing group is preferably a monovalent group having an epoxy group, more preferably a group represented by " ^--Leo --epoxy group". L ^eo is a single bond or a divalent linking group, an oxygen atom, an alkylene group (preferably a linear or branched alkylene group having 1 to 6 carbon atoms), or a group consisting of a combination thereof preferable.
Among them, the monovalent group having an epoxy group is preferably "--O-alkylene group-epoxy group". The alkylene group is preferably a linear or branched alkylene group having 1 to 6 carbon atoms, more preferably a methylene group.
When there are multiple epoxy group-containing groups, the epoxy group-containing groups may be the same or different.

R ^S5E in -CR ^S5E R ^S6E - represents a hydrogen atom or a substituent.
R ^S6E in -CR ^S5E R ^S6E - represents an aryl group having an epoxy group-containing group as a substituent.
The epoxy group-containing group referred to here is the same as the epoxy group-containing group described above.
The aryl group in the aryl group having an epoxy group-containing group as a substituent may be monocyclic or polycyclic. The number of carbon atoms in the aryl group is preferably 6 to 15, more preferably 6.
In the aryl group having an epoxy group-containing group as a substituent, the number of epoxy group-containing groups as substituents is 1 or more, preferably 1 to 5, more preferably 1 to 2. The aryl group in the aryl group having an epoxy group-containing group as a substituent may have a substituent other than the epoxy group-containing group.
The aryl group having an epoxy group-containing group as a substituent is preferably a phenyl group having 1 to 2 epoxy group-containing groups as a substituent, more preferably a phenyl group having an epoxy group-containing group at the para position.

Among them, L ^S2E is preferably an aromatic ring group having an epoxy group-containing group as a substituent, more preferably a benzene ring group having one or two epoxy group-containing groups as a substituent, and one or two substituents. A 1,2-benzenediyl group having one epoxy group-containing group is more preferred.

(general formula (1E))
The spiroepoxy compound is more preferably a compound represented by the general formula (1E) from the viewpoint that the effects of the present invention are more excellent.

ns1, ns2, AS, ^DS , ^RSA , ^RSB , ^RSC , and ^RSD in general formula (1E ⁾ are ns1 , ns2, A ^S , D ^S , R ^SA , R ^SB , R ^SC , and R ^SD , respectively.
In general formula (1E), ^REP represents an epoxy group-containing group.
The epoxy group-containing group of ^REP is the same as the epoxy group-containing group mentioned in the explanation of general formula (SE).
A plurality of ^REPs may be the same or different.

(general formula (2E))
The spiroepoxy compound is more preferably a compound represented by the general formula (2E) from the viewpoint that the effects of the present invention are more excellent.

ns1, ns2, R ^SA , R ^SB , R ^SC and R ^SD in general formula (2E) are ns1, ns2, R ^SA , The same is true for R ^SB , R ^SC and R ^SD respectively.
^REP in general formula (2E) is the same as ^REP in general formula (1E).

The lower limit of the molecular weight of the spiroepoxy compound is preferably 300 or more, preferably 400 or more, and more preferably 450 or more, from the viewpoint that the effects of the present invention are more excellent. The upper limit is preferably 700 or less, more preferably 550 or less.

The lower limit of the epoxy group content of the spiroepoxy compound is preferably 2.0 mmol/g or more, more preferably 3.5 mmol/g or more, and still more preferably 4.0 mmol/g or more, from the viewpoint that the effect of the present invention is more excellent. . The upper limit is preferably 20.0 mmol/g or less, more preferably 10.0 mmol/g or less.
In addition, the said epoxy group content intends the number of epoxy groups which 1g of epoxy compounds have.

<Other epoxy compounds>
Epoxy compounds may include other epoxy compounds other than spiroepoxy compounds.
Other epoxy compounds are compounds having at least one epoxy group (oxiranyl group) in one molecule. Epoxy groups may be substituted or unsubstituted where possible.
The number of epoxy groups possessed by other epoxy compounds is preferably 2 or more, more preferably 2 to 40, still more preferably 2 to 10, and particularly preferably 2, in one molecule.
Other epoxy compounds preferably have a molecular weight of 150 to 10,000, more preferably 150 to 2,000.

The epoxy group content of other epoxy compounds is preferably 2.0 to 20.0 mmol/g, more preferably 5.0 to 15.0 mmol/g.
In addition, the said epoxy group content intends the number of epoxy groups which 1g of epoxy compounds have.
The epoxy compound may be liquid at normal temperature (23° C.).

Other epoxy compounds may or may not exhibit liquid crystallinity.
That is, other epoxy compounds may be liquid crystal compounds. In other words, it may be a liquid crystal compound having an epoxy group.
Other epoxy compounds (which may be other liquid crystalline epoxy compounds) include, for example, a compound at least partially containing a rod-like structure (rod-like compound), and a compound disc containing at least partially a discotic structure compound.
The rod-like compound and discotic compound are described in detail below.

<Rod-shaped compound>
Other epoxy compounds that are rod-like compounds include azomethines, azoxys, cyanobiphenyls, cyanophenyl esters, benzoic acid esters, cyclohexanecarboxylic acid phenyl esters, cyanophenylcyclohexanes, cyano-substituted phenylpyrimidines, alkoxy Substituted phenylpyrimidines, phenyldioxanes, tolans, and alkenylcyclohexylbenzonitriles. Not only low-molecular-weight compounds as described above, but also high-molecular-weight compounds can be used. The polymer compound is a polymer compound in which a rod-shaped compound having a low-molecular-weight reactive group is polymerized.
Preferred rod-shaped compounds include rod-shaped compounds represented by the following general formula (XXI).
General formula (XXI): Q ¹ -L ¹¹¹ -A ¹¹¹ -L ¹¹³ -ML ¹¹⁴ -A ¹¹² -L ¹¹² -Q ²

In general formula (XXI), Q ¹ and Q ² are each independently an epoxy group, and L ¹¹¹ , L ¹¹² , L ¹¹³ and L ¹¹⁴ each independently represent a single bond or a divalent linking group. . A ¹¹¹ and A ¹¹² each independently represent a divalent linking group (spacer group) having 1 to 20 carbon atoms. M represents a mesogenic group.
The epoxy groups of Q ¹ and Q ² may or may not have a substituent.

In general formula (XXI), L ¹¹¹ , L ¹¹² , L ¹¹³ and L ¹¹⁴ each independently represent a single bond or a divalent linking group.
The divalent linking groups represented by L ¹¹¹ , L ¹¹² , L ¹¹³ and L ¹¹⁴ are each independently -O-, -S-, -CO-, -NR ¹¹² - and -CO-O -, -O-CO-O-, -CO-NR ¹¹² -, -NR ¹¹² -CO-, -O-CO-, -CH ₂ -O-, -O-CH ₂ -, -O-CO-NR It is preferably a divalent linking group selected from the group consisting of ^112- , -NR ¹¹² -CO-O- and -NR ¹¹² -CO-NR ^112- . R ¹¹² above is an alkyl group having 1 to 7 carbon atoms or a hydrogen atom.
Among them, L ¹¹³ and L ¹¹⁴ are each independently preferably -O-.
L ¹¹¹ and L ¹¹² are each independently preferably a single bond.

In general formula (XXI), A ¹¹¹ and A ¹¹² each independently represent a divalent linking group having 1 to 20 carbon atoms.
The divalent linking group may contain non-adjacent heteroatoms such as oxygen and sulfur atoms. Among them, an alkylene group, an alkenylene group, or an alkynylene group having 1 to 12 carbon atoms is preferable. The above alkylene group, alkenylene group, or alkynylene group may or may not have an ester group.
The divalent linking group is preferably linear, and the divalent linking group may or may not have a substituent. Examples of substituents include halogen atoms (fluorine, chlorine and bromine atoms), cyano groups, methyl groups and ethyl groups.
Among them, A ¹¹¹ and A ¹¹² are each independently preferably an alkylene group having 1 to 12 carbon atoms, more preferably a methylene group.

In general formula (XXI), M represents a mesogenic group, and examples of the mesogenic group include known mesogenic groups. Among them, a group represented by the following general formula (XXII) is preferable.
general formula (XXII): -(W ¹ -L ¹¹⁵ ) _n -W ² -

In formula (XXII), W ¹ and W ² each independently represent a divalent cyclic alkylene group, a divalent cyclic alkenylene group, an arylene group, or a divalent heterocyclic group. L ¹¹⁵ represents a single bond or a divalent linking group. n represents an integer of 1-4.

Examples of W ¹ and W ² include 1,4-cyclohexenediyl, 1,4-cyclohexanediyl, 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. In the case of 1,4-cyclohexanediyl, it may be either trans- or cis-structural isomers, or may be a mixture of any ratio. Among them, the trans form is preferred.
W ¹ and W ² may each have a substituent. Examples of substituents include groups exemplified in the above-described substituent group Y, more specifically, halogen atoms (fluorine atom, chlorine atom, bromine atom, and iodine atom), cyano group, carbon 1 to 10 alkyl groups (e.g., methyl group, ethyl group, and propyl group), alkoxy groups with 1 to 10 carbon atoms (e.g., methoxy group, ethoxy group, etc.), 1 to 10 carbon atoms acyl group (e.g., formyl group, acetyl group, etc.), alkoxycarbonyl group having 1 to 10 carbon atoms (e.g., methoxycarbonyl group, ethoxycarbonyl group, etc.), acyloxy group having 1 to 10 carbon atoms (e.g., acetyloxy group, propionyloxy group, etc.), nitro group, trifluoromethyl group, difluoromethyl group and the like.
When there are multiple ^W1 's, the multiple ^W1 's may be the same or different.

In general formula (XXII), ^L115 represents a single bond or a divalent linking group. Specific examples of the divalent linking group represented by L ¹¹⁵ include the divalent linking groups represented by L ¹¹¹ to L ¹¹⁴ described above, for example, -CO-O-, -O-CO- , —CH ₂ —O—, and —O—CH ₂ —.
When multiple L ¹¹⁵ are present, the multiple L ¹¹⁵ may be the same or different.

Preferred basic skeletons of the mesogenic group represented by the above general formula (XXII) are exemplified below. In the mesogenic group, these skeletons may be substituted with a substituent.

Among the skeletons described above, a biphenyl skeleton is preferable because the obtained thermally conductive material has more excellent thermal conductivity.
Incidentally, the compound represented by the general formula (XXI) can be synthesized by referring to the method described in JP-A-11-513019 (WO97/00600).
The rod-shaped compound may be a monomer having a mesogenic group as described in JP-A-11-323162 and JP-A-4118691.

The rod-shaped compound is also preferably a compound represented by general formula (E1).

In general formula (E1), each L ^E1 independently represents a single bond or a divalent linking group.
Among them, L ^E1 is preferably a divalent linking group.
Divalent linking groups are -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 is preferred, and -O-alkylene group- or -alkylene group -O- is more preferred.
The alkylene group may be linear, branched, or cyclic, but a linear alkylene group having 1 to 2 carbon atoms is preferred.
Multiple L ^E1 may be the same or different.

In general formula (E1), L ^E2 is each independently a single bond, -CH=CH-, -CO-O-, -O-CO-, -C(-CH ₃ )=CH-, -CH= C(-CH ₃ )-, -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 represents (-CN)- or -C(-CN)=CH-.
Among them, each L ^E2 is preferably independently a single bond, —CO—O—, or —O—CO—.
When a plurality of ^LE2 are present, the plurality of ^LE2 may be the same or different.

In general formula (E1), L ^E3 is each independently a single bond, or an optionally substituted 5- or 6-membered aromatic ring group or a 5- or 6-membered ring or a polycyclic group consisting of these rings.
Examples of the aromatic ring group and non-aromatic ring group represented by L ^E3 include optionally substituted 1,4-cyclohexanediyl group, 1,4-cyclohexenediyl group, 1,4 -phenylene group, pyrimidine-2,5-diyl group, pyridine-2,5-diyl group, 1,3,4-thiadiazole-2,5-diyl group, 1,3,4-oxadiazole-2,5 -diyl group, naphthalene-2,6-diyl group, naphthalene-1,5-diyl group, thiophene-2,5-diyl group, and pyridazine-3,6-diyl group. In the case of a 1,4-cyclohexanediyl group, it may be either a trans or cis structural isomer, or a mixture of any ratio. Among them, the trans form is preferred.
Among them, L ^E3 is preferably a single bond, a 1,4-phenylene group, or a 1,4-cyclohexenediyl group.
The substituents possessed by the group represented by L ^E3 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). preferable.
In addition, when a plurality of substituents are present, the substituents may be the same or different.
When there are a plurality of ^LE3s , the plurality of ^LE3s may be the same or different.

In general formula (E1), pe represents an integer of 0 or more.
When pe is an integer of 2 or more, a plurality of (-L ^E3 -L ^E2 -) may be the same or different.
Among them, pe is preferably 0 to 2, more preferably 0 or 1, and still more preferably 0.

In general 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, and more preferably an alkyl group (preferably having 1 carbon atom).
A plurality of ^LE4 may be the same or different. Further, when le, which will be described below, is an integer of 2 or more, multiple ^LE4s present in the same (L ^E4 ) _le may be the same or different.

In general formula (E1), each le independently represents an integer of 0 to 4.
Among them, each le is preferably independently 0 to 2.
A plurality of le's may be the same or different.

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

<Disk-shaped compound>
Other epoxy compounds that are discotic compounds have an at least partially discotic structure.
The discotic structure has at least an alicyclic or aromatic ring. In particular, when the discotic structure has an aromatic ring, the discotic compound can form a columnar structure through the formation of a stacking structure due to intermolecular π-π interaction.
As a disk-shaped structure, specifically, Angew. Chem. Int. Ed. 2012, 51, 7990-7993 or the triphenylene structure described in JP-A-7-306317, and the trisubstituted benzene structure described in JP-A-2007-2220 and JP-A-2010-244038.

If a discotic compound is used as another epoxy compound, a thermally conductive material exhibiting high thermal conductivity can be obtained. The reason for this is that while the rod-shaped compound can only conduct heat linearly (one-dimensionally), the discotic compound can conduct heat two-dimensionally in the normal direction. It is thought that the thermal conductivity is improved.

The discotic compound preferably has three or more epoxy groups. A cured product of a 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 possessed by the discotic compound is preferably 8 or less, more preferably 6 or less.

Specific examples of discotic compounds include C.I. Destrade et al. , Mol. Crysr. Liq. Cryst. , vol. 71, page 111 (1981); edited by The Chemical Society of Japan, Quarterly Kagaku Sosetsu, No. 22, Liquid Crystal Chemistry, Chapter 5, Chapter 10 Section 2 (1994); Kohne et al. , Angew. Chem. Soc. Chem. Comm. , page 1794 (1985); Zhang et al. , J. Am. Chem. Soc. , vol. 116, page 2655 (1994), and compounds having at least one terminal (preferably three or more) of epoxy groups in the compounds described in Japanese Patent No. 4,592,225.
As the discotic compound, Angew. Chem. Int. Ed. 2012, 51, 7990-7993, and JP-A-7-306317, in a triphenylene structure having a triphenylene as a central ring, at least one (preferably 3 or more, more preferably 3 to 6) at the end ) as an epoxy group, and in a 3-substituted benzene structure with a benzene ring as the central ring as described in JP-A-2007-2220 and JP-A-2010-244038. Examples thereof include compounds having at least one epoxy group (preferably at least 3, more preferably 3).

Other epoxy compounds other than those described above include, for example, epoxy compounds represented by general formula (DN).

In general formula (DN), n ^DN represents an integer of 0 or more, preferably 0 to 5, more preferably 1.
R ^DN represents a single bond or a divalent linking group. The divalent linking group includes -O-, -O-CO-, -CO-O-, -S-, an alkylene group (having preferably 1 to 10 carbon atoms), an arylene group (having a carbon number of 6 to 20 are preferred.) or a group consisting of a combination thereof, more preferably an alkylene group, and more preferably a methylene group.

Other epoxy compounds include compounds in which the epoxy group is ring-condensed. Examples of such compounds include 3,4:8,9-diepoxybicyclo[4.3.0]nonane and the like.

Other epoxy compounds include, for example, bisphenol A-type epoxy compounds, bisphenol F-type epoxy compounds, bisphenol S-type epoxy compounds, and bisphenol AD-type epoxy compounds, which are glycidyl ethers of bisphenol A, F, S, and AD. etc.; hydrogenated bisphenol A-type epoxy compound, hydrogenated bisphenol AD-type epoxy compound, etc.; A novolac type glycidyl ether, etc.; dicyclopentadiene type glycidyl ether (dicyclopentadiene type epoxy compound); dihydroxypentadiene type glycidyl ether (dihydroxypentadiene type epoxy compound); polyhydroxybenzene type glycidyl ether (1,3- polyhydroxybenzene-type epoxy compounds such as phenylene bis(glycidyl ether); benzenepolycarboxylic acid-type glycidyl esters (benzenepolycarboxylic acid-type epoxy compounds); and trisphenolmethane-type epoxy compounds.

Other epoxy compounds may be used individually by 1 type, and may use 2 or more types.

In the composition of the present invention, when the phenol compound contains a spirophenol compound and the epoxy compound contains a spiroepoxy compound, for example, the content of the spirophenol compound is 50% by mass or more based on the total phenol compounds, and , the content of the spiroepoxy compound may be less than 5% by mass based on the total epoxy compound. Further, for example, the content of the spirophenol compound may be less than 5% by mass with respect to all phenol compounds, and the content of the spiroepoxy compound may be 50% by mass or more with respect to all epoxy compounds.

The ratio of the content of epoxy compounds to the content of phenolic compounds in the composition is such that the equivalent ratio of epoxy groups of all epoxy compounds to hydroxyl groups of all phenolic compounds (number of epoxy groups/number of hydroxyl groups) is 30. /70 to 70/30 is preferred, 40/60 to 60/40 is more preferred, and 45/55 to 55/45 is even more preferred.
In addition, the ratio of the content of all epoxy compounds to the content of all phenolic compounds in the composition is the equivalent ratio (epoxy group / number of active hydrogen) is preferably 30/70 to 70/30, more preferably 40/60 to 60/40, and even more preferably 45/55 to 55/45. .
In the composition of the present invention, the equivalent ratio of the total number of epoxy groups in the solid content to the total number of hydroxyl groups (preferably phenolic hydroxyl groups) in the solid content (number of epoxy groups/number of hydroxyl groups) number) is preferably 30/70 to 70/30, more preferably 40/60 to 60/40, even more preferably 45/55 to 55/45.
In the composition of the present invention, the equivalent ratio of the total number of epoxy groups in the solid content to the total number of active hydrogens in the solid content (number of epoxy groups/number of active hydrogens) is 30. /70 to 70/30 is preferred, 40/60 to 60/40 is more preferred, and 45/55 to 55/45 is even more preferred.
In addition, solid content intends the component which forms a thermally-conductive material, and a solvent is not included. The component forming the thermally conductive material referred to here may be a component that reacts (polymerizes) to change its chemical structure when forming the thermally conductive material. In addition, as long as it is a component that forms a thermally conductive material, it is regarded as a solid content even if its property is liquid.

Further, the total content of the epoxy compound and the phenol compound in the composition is preferably 5 to 90% by mass, more preferably 10 to 50% by mass, and 15 to 40% by mass, based on the total solid content of the composition. is more preferred.

[Inorganic matter]
The composition includes inorganic matter.
As the inorganic substance, any inorganic substance conventionally used as an inorganic filler for thermally conductive materials may be used. As the inorganic substance, an inorganic nitride or an inorganic oxide is preferable from the viewpoint of better thermal conductivity and insulating properties of the thermally conductive material.

The shape of the inorganic substance is not particularly limited, and may be particulate, film-like, or plate-like. Examples of the shape of the particulate inorganic material include rice grain, spherical, cubic, spindle, scale, aggregate, and irregular shapes.

Examples of inorganic oxides include zirconium oxide (ZrO ₂ ), titanium oxide (TiO ₂ ), silicon oxide (SiO ₂ ), aluminum oxide (Al ₂ O ₃ ), iron oxide (Fe ₂ O ₃ , FeO, Fe ₃ O ₄ ), copper oxides (CuO, Cu ₂ O), zinc oxide (ZnO), yttrium oxide (Y ₂ O ₃ ), niobium oxide (Nb ₂ O ₅ ), molybdenum oxide (MoO ₃ ), indium oxide (In ₂ O ₃ , In ₂ O), tin oxide (SnO ₂ ), tantalum oxide (Ta ₂ O ₅ ), tungsten oxide (WO ₃ , W ₂ O ₅ ), lead oxide (PbO, PbO ₂ ), bismuth oxide (Bi ₂ O ₃ ), cerium oxide (CeO ₂ , Ce ₂ O ₃ ), antimony oxide (Sb ₂ O ₃ , Sb ₂ O ₅ ), germanium oxide (GeO ₂ , GeO), lanthanum oxide (La ₂ O ₃ ), and Ruthenium oxide (RuO ₂ ) and the like are included.
Only one kind of the above inorganic oxides may be used, or two or more kinds thereof may be used.
The inorganic oxide is preferably titanium oxide, aluminum oxide, or zinc oxide, more preferably aluminum oxide.
The inorganic oxide may be an oxide produced by oxidizing a metal prepared as a non-oxide in the environment or the like.

Examples of inorganic nitrides include boron nitride (BN), carbon nitride ( _C3N4 ), silicon nitride ( _Si3N4 ), gallium nitride ( _GaN ), indium nitride (InN), aluminum nitride ( _AlN ), Chromium nitride ( _Cr2N ), copper nitride (Cu3N), iron nitride ( _Fe4N ), iron nitride ( _Fe3N ) _, lanthanum nitride (LaN), lithium nitride ( _Li3N ), magnesium nitride (Mg _{3N 2} ), molybdenum nitride (Mo ₂ N), niobium nitride (NbN), tantalum nitride (TaN), titanium nitride (TiN), tungsten nitride (W ₂ N), tungsten nitride (WN ₂ ), yttrium nitride (YN ), and zirconium nitride (ZrN).
Only one kind of the above inorganic nitrides may be used, or two or more kinds thereof may be used.
The inorganic nitride preferably contains aluminum atoms, boron atoms, or silicon atoms, more preferably aluminum nitride, boron nitride, or silicon nitride, more preferably aluminum nitride or boron nitride, It is particularly preferred to contain boron nitride.

Although the size of the inorganic substance is not particularly limited, the average particle size of the inorganic substance is preferably 500 μm or less, more preferably 300 μm or less, and even more preferably 200 μm or less, in terms of better dispersibility of the inorganic matter. Although the lower limit is not particularly limited, it is preferably 10 nm or more, more preferably 100 nm or more, in terms of handleability.
As for the average particle diameter of the inorganic substance, the catalog value is adopted when using a commercially available product. If there is no catalog value, the method for measuring the average particle size is to use an electron microscope to randomly select 100 inorganic substances, measure the particle size (major axis) of each inorganic substance, and calculate the find the average.

Only one kind of inorganic substance may be used, or two or more kinds thereof may be used.
From the viewpoint that the effect of the present invention is more excellent, the inorganic substance preferably contains at least one of an inorganic nitride and an inorganic oxide, more preferably contains at least an inorganic nitride, and both an inorganic nitride and an inorganic oxide. It is further preferred to include
From the viewpoint that the effect of the present invention is more excellent, the inorganic nitride preferably contains at least one of boron nitride and aluminum nitride, and more preferably contains at least boron nitride.
The content of the inorganic nitride (preferably boron nitride and/or aluminum nitride) in the inorganic substance is preferably 10 to 100% by mass, more preferably 40 to 100% by mass, based on the total mass of the inorganic substance.
Aluminum oxide is preferable as the inorganic oxide.
The composition more preferably contains at least inorganic particles having an average particle size of 20 μm or more (preferably 40 μm or more), in order to improve the thermal conductivity of the heat conductive material.

From the viewpoint that the effect of the present invention is more excellent, the content of inorganic substances in the composition is preferably 40 to 95% by mass, more preferably 50 to 95% by mass, and 60 to 95% by mass, based on the total solid content of the composition. % by mass is more preferred.

[Surface modifier]
The composition of the present invention may further contain a surface modifier from the viewpoint of improving the thermal conductivity of the thermally conductive material.
A surface modifier is a component that modifies the surface of the above-mentioned inorganic substance.
As used herein, "surface modification" means a state in which an organic substance is adsorbed on at least a part of the surface of an inorganic substance. The form of adsorption is not particularly limited as long as it is in a bound state. In other words, the surface modification includes a state in which an organic group obtained by desorption of a part of the organic substance is bonded to the surface of the inorganic substance. The bond may be any bond such as covalent bond, coordinate bond, ionic bond, hydrogen bond, van der Waals bond, and metallic bond. The surface modification may be such as to form a monomolecular film on at least part of the surface. Monolayers are monolayer films formed by chemisorption of organic molecules and are known as Self-Assembled MonoLayers (SAMs). In addition, in this specification, the surface modification may be only a part of the surface of the inorganic substance, or may be the whole surface. As used herein, the term “surface-modified inorganic substance” means an inorganic substance whose surface has been modified with a surface modifier, that is, a substance in which an organic substance is adsorbed on the surface of the inorganic substance.
That is, in the composition of the present invention, the inorganic substance may constitute a surface-modified inorganic substance (preferably a surface-modified inorganic nitride and/or a surface-modified inorganic oxide) in cooperation with a surface modifier.
The surface modifier and the phenolic compound and epoxy compound described above are preferably different compounds.

As the surface modifier, conventionally known surface modifiers such as carboxylic acids such as long-chain alkyl fatty acids, organic phosphonic acids, organic phosphoric acid esters, and organic silane molecules (silane coupling agents) can be used. In addition, for example, surface modifiers described in JP-A-2009-502529, JP-A-2001-192500, and JP-A-4694929 may be used.

In addition, the composition preferably contains a compound having a condensed ring skeleton or a triazine skeleton as a surface modifier (preferably when the inorganic substance contains an inorganic nitride (such as boron nitride and/or aluminum nitride)).
The condensed ring skeleton is preferably a condensed ring skeleton between aromatic rings.
Such a surface modifier (preferably surface modifier A and/or surface modifier B described later) is preferably used as a surface modifier for inorganic nitrides.

<Surface modifier A>
As the surface modifier, for example, surface modifier A described below is preferable. In addition, the surface modifier A is a surface modifier having a condensed ring skeleton.
The surface modifier A satisfies the following conditions 1 and 2.
- Condition 1: It has a functional group (hereinafter also referred to as "specific functional group A") selected from the functional group group P shown below.

(Functional group group P)
Boronic acid group (-B(OH) ₂ ), aldehyde group (-CHO), isocyanate group (-N=C=O), isothiocyanate group (-N=C=S), cyanate group (-O-CN) , acyl azide group, succinimide group, sulfonyl chloride group (—SO ₂ Cl), carboxylic acid chloride group (—COCl), onium group, carbonate group (—O—CO—O—), aryl halide group, carbodiimide group ( -N=C=N-), an acid anhydride group (-CO-O-CO-, or monovalent acid anhydrides such as maleic anhydride, phthalic anhydride, pyromellitic anhydride, and trimellitic anhydride group), carboxylic acid group (—COOH), phosphonic acid group (—PO(OH) ₂ ), phosphinic acid group (—HPO(OH)), phosphoric acid group (—OP(=O)(OH) ₂ ), Phosphate ester group (-OP(=O)(OR ^B ) ₂ ), sulfonic acid group (-SO ₃ H), halogenated alkyl group, nitrile group (-CN), nitro group (-NO ₂ ), ester group (-CO-O- or -O-CO-), carbonyl group (-CO-), imide ester group (-C(=NR _C )-O- or -OC(=NR _C )-), alkoxy Silyl group, acryl group (-OCOCH ₂ =CH ₂ ), methacryl group (-OCOCH(CH ₃ )=CH ₂ ), oxetanyl group, vinyl group (-CH=CH ₂ ), alkynyl group (one hydrogen atom from alkyne) (e.g., ethynyl group, prop-2-yn-1-yl group, etc.), maleimide group, thiol group (-SH), hydroxyl group (-OH), halogen atom (F atom, Cl atom, Br atom, and I atom), and a functional group selected from the group consisting of an amino group.

The acylazido group intends a group represented by the structure below. Note that * in the formula represents a bonding position. The counter anion (Z ⁻ ) of the acylazide group is not particularly limited, and examples thereof include halogen ions.

The above succinimide group, oxetanyl group, and maleimide group each represent a group formed by removing one hydrogen atom at an arbitrary position from the compound represented by the following formula.

Further, the onium group means a group having an onium salt structure. An onium salt is a compound that is formed by coordinating a compound with an electron pair that does not participate in a chemical bond with another cationic form of the compound through the electron pair. Onium salts typically contain a cation and an anion.
The onium salt structure is not particularly limited, but examples include an ammonium salt structure, a pyridinium salt structure, an imidazolium salt structure, a pyrrolidinium salt structure, a piperidinium salt structure, a triethylenediamine salt structure, a phosphonium salt structure, a sulfonium salt structure, and a thiopyrylium salt structure. etc. The type of the counter anion is not particularly limited, and known anions are used. The valence of the anion is also not particularly limited, and examples thereof include 1 to 3 valences, preferably 1 to 2 valences.
As the onium group, among others, a group having an ammonium salt structure represented by the following general formula (A1) is preferable.

In general formula (A1), R ^1A to R ^3A each independently represent a hydrogen atom or an alkyl group (both linear, branched and cyclic). The number of carbon atoms in the alkyl group is, for example, 1-10, preferably 1-6, more preferably 1-3. M ⁻ represents an anion.
* represents a binding position. In addition, the alkyl group may further have a substituent (for example, substituent group Y).

The aryl halide group is not particularly limited as long as it is an aromatic ring group substituted with one or more halogen atoms. The aromatic ring group may have either a monocyclic structure or a polycyclic structure, but is preferably a phenyl group. Moreover, the halogen atom includes a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and a fluorine atom is preferable. In addition, the aryl halide group may further have a substituent (for example, substituent group Y).

Specific examples of the aryl halide group include a fluorophenyl group, a perfluorophenyl group, a chlorophenyl group, a bromophenyl group, an iodophenyl group, and the like.

The phosphate ester group is not particularly limited as long as it is a group represented by —OP(=O)(OR ^B ) ₂ . Examples of ^RB include a hydrogen atom and a monovalent organic group. However, at least one of ^RB represents a monovalent organic group. Monovalent organic groups include, for example, alkyl groups (both linear, branched and cyclic) and aryl groups. The number of carbon atoms in the alkyl group is, for example, 1-10, preferably 1-6, more preferably 1-3. In addition, the alkyl group may further have a substituent (for example, substituent group Y). Moreover, the aryl group is not particularly limited, but examples thereof include a phenyl group and a pyrenyl group.

Although the above-mentioned halogenated alkyl group is not particularly limited, examples thereof include groups in which an alkyl group having 1 to 10 carbon atoms is substituted with one or more halogen atoms. The number of carbon atoms in the alkyl group (both linear, branched and cyclic) is preferably 1-6, more preferably 1-3. A halogen atom includes a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and a fluorine atom, a chlorine atom, or a bromine atom is preferable. In addition, the halogenated alkyl group may further have a substituent (for example, substituent group Y).

The imidoester group is not particularly limited as long as it is a group represented by -C(=NR ^C )-O- or -OC(=NR ^C )-. Examples of R 2 ^C include a hydrogen atom and an alkyl group (both linear, branched and cyclic). The number of carbon atoms in the alkyl group is, for example, 1-10, preferably 1-6, more preferably 1-3. In addition, the alkyl group may further have a substituent (for example, substituent group Y).
The imidoester group may have an onium salt structure in which an electron pair that does not participate in the chemical bond of the imine nitrogen is coordinated with another cation (for example, a hydrogen ion).

Although the alkoxysilyl group is not particularly limited, examples thereof include groups represented by the following general formula (A2).

General formula (A2): *-Si(OR ^D ) ₃
In general formula (A2), ^RD each independently represents an alkyl group (including both linear, branched and cyclic). * represents a binding position.
The alkyl group represented by R ^D includes, for example, an alkyl group having 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms, more preferably 1 to 3 carbon atoms.
Specific examples include a trimethoxysilyl group and a triethoxysilyl group.
In addition, the alkyl group may further have a substituent (for example, substituent group Y).

The amino group is not particularly limited and may be primary, secondary or tertiary. Specifically, -N(R ^E ) ₂ (each R ^E is independently a hydrogen atom or an alkyl group (including linear, branched and cyclic)). The number of carbon atoms in the alkyl group is, for example, 1-10, preferably 1-6, more preferably 1-3. In addition, the alkyl group may further have a substituent (for example, substituent group Y).

The number of the specific functional groups A in the surface modifier A is not particularly limited as long as it is 1 or more. Moreover, although the upper limit is not specifically limited, 15 or less is preferable. Among them, 1 to 8 are preferable, 1 to 3 are more preferable, and 1 or 2 is even more preferable in terms of better dispersibility of the surface-modified inorganic nitride.

- Condition 2: It has a condensed ring structure containing two or more rings selected from the group consisting of aromatic hydrocarbon rings and aromatic heterocycles.

Although the aromatic hydrocarbon ring is not particularly limited, examples thereof include a 5-membered or more monocyclic aromatic hydrocarbon ring. Although the upper limit of the number of ring members is not particularly limited, it is often 10 or less. The aromatic hydrocarbon ring is preferably a 5- or 6-membered monocyclic aromatic hydrocarbon ring.
Examples of aromatic hydrocarbon rings include cyclopentadienyl rings and benzene rings.

The aromatic heterocyclic ring is not particularly limited, but includes, for example, a 5-membered or more monocyclic aromatic hydrocarbon ring. Although the upper limit of the number of ring members is not particularly limited, it is often 10 or less. As the aromatic heterocycle, for example, a 5- or 6-membered monocyclic aromatic heterocycle is preferred.
Examples of aromatic heterocyclic rings include thiophene ring, thiazole ring, imidazole ring, pyridine ring, pyridazine ring, pyrimidine ring, pyrazine ring, and triazine ring.

The condensed structure is not particularly limited as long as it is a condensed ring structure containing two or more rings selected from the group consisting of aromatic hydrocarbon rings and aromatic heterocycles. A condensed ring structure containing two or more group hydrocarbon rings is preferred, a condensed ring structure containing two or more benzene rings is more preferred, and a condensed ring structure containing three or more benzene rings is even more preferred. Although the upper limit of the number of aromatic hydrocarbon rings and aromatic heterocyclic rings contained in the condensed structure is not particularly limited, it is often 10 or less, for example.
Specific examples of condensed ring structures containing two or more aromatic hydrocarbon rings include biphenylene, indacene, acenaphthylene, fluorene, phenalene, phenanthrene, anthracene, fluoranthene, acephenanthrylene, aceanthrylene, pyrene, chrysene, and tetracene. , pleiadene, picene, perylene, pentaphene, pentacene, tetraphenylene, hexaphene, and triphenylene. A condensed structure comprising two or more condensed rings is more preferable, a condensed structure comprising three or more benzene rings is more preferable, and a condensed structure composed of pyrene or perylene is particularly preferable.

The surface modifier A is preferably a compound represented by the general formula (V1), more preferably a compound represented by the general formula (V2), in terms of further improving dispersibility.
The compound represented by the general formula (V1) and the compound represented by the general formula (V2) are described below.
(Compound represented by general formula (V1))

In general formula (V1), X represents an n-valent organic group having a condensed ring structure containing two or more rings selected from the group consisting of aromatic hydrocarbon rings and aromatic heterocyclic rings.

X above represents an n-valent organic group (n is an integer of 1 or more). n is not particularly limited as long as it is an integer of 1 or more. Although the upper limit is not particularly limited, it is preferably an integer of 15 or less. Among them, 1 to 8 are preferable, 1 to 3 are more preferable, and 1 or 2 is even more preferable in terms of better dispersibility of the surface-modified inorganic nitride.

Examples of the condensed ring structure containing two or more rings selected from the group consisting of aromatic hydrocarbon rings and aromatic heterocycles in X include the structures described above, and preferred embodiments are also the same.

The n-valent organic group represented by X is not particularly limited as long as it has a condensed ring structure containing two or more rings selected from the group consisting of aromatic hydrocarbon rings and aromatic heterocycles. It is preferably a group formed by extracting n hydrogen atoms from a condensed ring containing two or more rings selected from the group consisting of aromatic hydrocarbon rings and aromatic heterocycles, from the viewpoint of better effects of the invention. .
The condensed structure may further have a substituent (for example, substituent group Y) in addition to the specific functional group A.

Y above is a monovalent group represented by the following general formula (B1), a monovalent group represented by the following general formula (B2), or a monovalent group represented by the following general formula (B4). Alternatively, when n represents an integer of 2 or more, it represents a divalent group represented by the following general formula (B3) in which a plurality of Y are bonded.
In other words, when n is 1, Y is a monovalent group represented by the following general formula (B1), a monovalent group represented by the following general formula (B2), or the following general formula represents a monovalent group represented by (B4);
When n represents an integer of 2 or more, Y is a monovalent group represented by the following general formula (B1), a monovalent group represented by the following general formula (B2), or the following general formula It represents a monovalent group represented by (B4), or represents a divalent group represented by the following general formula (B3) in which a plurality of Y are bonded. In addition, when n is 2 or more, multiple Y may be the same or different.
When Y represents a divalent group represented by general formula (B3) below, the compound represented by general formula (V1) is represented by general formula (V3) below.

In general formula (V3), X has the same definition as X in general formula (V1) described above. L ³ has the same meaning as L ³ in general formula (B3) described later.

General formula (B1): * ¹ -L ¹ -P ¹
In general formula (B1), ^L1 represents a single bond or a divalent linking group.
The divalent linking group is not particularly limited, but examples include -O-, -S-, -NR ^F - (R ^F represents a hydrogen atom or an alkyl group), divalent hydrocarbon groups (e.g. , an alkylene group, an alkenylene group (e.g. -CH=CH-), an alkynylene group (e.g. -C≡C-), and an arylene group), a divalent organic group (carbonate group ( -O-CO-O-), carbodiimide group (-N=C=N-), acid anhydride group (-CO-O-CO-), ester group (-CO-O- or -O-CO-) , a carbonyl group (-CO-), an imide ester group (-C(=NR ^C )-O- or -O-C(=NR ^C )-)), or a combination thereof.
Examples of the combined groups include -(divalent hydrocarbon group)-X ¹¹¹ -, -X ¹¹¹ -(divalent hydrocarbon group)-, -(divalent hydrocarbon group)-X ¹¹¹ - (Divalent hydrocarbon group)-, -X ¹¹¹ -(Divalent hydrocarbon group) -X ¹¹¹ -(Divalent hydrocarbon group)-, or -(Divalent hydrocarbon group)-X ¹¹¹ -(divalent hydrocarbon group) -X ¹¹¹ - and the like. -X ¹¹¹ - is -O-, -S-, -NR ^F -, a divalent organic group in the functional group P described above, or a group combining these. The total number of carbon atoms in the combined group is, for example, 1-20, preferably 1-12.

P ¹ is a monovalent organic group (boronic acid group (-B(OH) ₂ ), aldehyde group (-CHO), isocyanate group (-N=C=O), iso thiocyanate group (-N=C=S), cyanate group (-O-CN), acylazide group, succinimide group, sulfonyl chloride group (-SO ₂ Cl), carboxylic acid chloride group (-COCl), onium group, Aryl halide group, acid anhydride group (maleic anhydride, phthalic anhydride, pyromellitic anhydride, and monovalent acid anhydride groups such as trimellitic anhydride), carboxylic acid group (-COOH) , phosphonic acid group (-PO(OH) ₂ ), phosphinic acid group (-HPO(OH)), phosphate group (-OP(=O)(OH) ₂ ), phosphate ester group (-OP(=O ) (OR ^B ) ₂ ), sulfonic acid group (--SO ₃ H), halogenated alkyl group, nitrile group (--CN), nitro group (--NO ₂ ), alkoxysilyl group, acryl group (--OCOCH ₂ =CH ₂ ), a methacryl group (--OCOCH(CH ₃ )=CH ₂ ), an oxetanyl group, a vinyl group (--CH=CH ₂ ), an alkynyl group (a group obtained by removing one hydrogen atom from an alkyne. For example, an ethynyl group, and prop-2-yn-1-yl group, etc.), maleimide group, thiol group (-SH), hydroxyl group (-OH), halogen atom (F atom, Cl atom, Br atom, and I atom)) represents
* ¹ represents the bonding position with the above X.

General formula (B2): * ² -L ² -P ²
In general formula (B2), L ² is a divalent organic group (carbonate group (-O-CO-O-), carbodiimide group (-N=C=N-), acid anhydride group (-CO-O-CO-), ester group (-CO-O- or -O-CO-), carbonyl group (-CO-), or imide ester group (-C (=NR ^C )- represents a divalent linking group including O— or —OC(=NR ^C )—)).
Examples of L ² include a divalent organic group in the functional group group P described above, or a divalent organic group in the functional group group P described above, —O—, —S—, and —NR ^F - (R ^F represents a hydrogen atom or an alkyl group.), and a divalent hydrocarbon group (e.g., an alkylene group, an alkenylene group (e.g., -CH=CH-), an alkynylene group (e.g., -C≡ C-) and a linking group selected from the group consisting of arylene group).
Examples of the combined group include -(divalent hydrocarbon group) -X ¹¹² -. -X ¹¹² - is a divalent organic group in the functional group group P described above, or a divalent organic group in the functional group group P described above, and -O-, -S-, and -NR It is a group in combination with a divalent group selected from ^F- . The total number of carbon atoms in the combined group is, for example, 1-20, preferably 1-12.

^P2 above represents a monovalent organic group. The monovalent organic group represented by ^P2 is not particularly limited, and examples thereof include an alkyl group. The number of carbon atoms in the alkyl group is, for example, 1-10, preferably 1-6, more preferably 1-3.
* ² represents the bonding position with X above.

General formula (B3): * ³¹ -L ³ -* ³²
In general formula (B3), L ³ is a divalent organic group (carbonate group (-O-CO-O-), carbodiimide group (-N=C=N-), acid anhydride group (-CO-O-CO-), ester group (-CO-O- or -O-CO-), carbonyl group (-CO-), or imidoester group (-C (=NR ^C )- represents a divalent linking group including O— or —OC(=NR ^C )—)).
Examples of L ³ include a divalent organic group in the functional group group P described above, or a divalent organic group in the functional group group P described above, —O—, —S—, and —NR ^F - (R ^F represents a hydrogen atom or an alkyl group.), and a divalent hydrocarbon group (e.g., an alkylene group, an alkenylene group (e.g., -CH=CH-), an alkynylene group (e.g., -C≡ C-) and a linking group selected from the group consisting of arylene group).
Examples of the combined groups include -(divalent hydrocarbon group)-X ¹¹³ -(divalent hydrocarbon group)-, -(divalent hydrocarbon group)-X ¹¹³ -, -X ¹¹³ - (Divalent hydrocarbon group)-, and -X ¹¹³ - (divalent hydrocarbon group) -X ¹¹³ - and the like. -X ¹¹³ - is a divalent organic group in the functional group group P described above, or a divalent organic group in the functional group group P described above, and -O-, -S-, and -NR It is a group in combination with a divalent group selected from ^F- . The total number of carbon atoms in the combined group is, for example, 1-20, preferably 1-12.
* ³¹ and * ³² represent the bonding positions with X above. That is, L ³ above forms a ring together with two different carbon atoms on the condensed ring structure represented by X above.

General formula (B4):

In general formula (B4), L ⁴ represents an m ¹¹ + monovalent linking group.
^m11 represents an integer of 2 or more. Although the upper limit of m ¹¹ is not particularly limited, it is, for example, 100 or less, preferably 30 or less, more preferably 20 or less, and even more preferably 15 or less. Although the lower limit of ^m11 is not particularly limited, it is preferably 4 or more.
The linking group represented by L ⁴ is not particularly limited, and examples thereof include an m ¹¹ + monovalent aromatic hydrocarbon ring and a group represented by the following general formula (M1).

In general formula (M1) above, X ²²¹ and X ²²² each independently represent a single bond or a divalent linking group. The divalent linking group represented by X ²²¹ and X ²²² has the same meaning as the divalent linking group represented by L ¹ in general formula (B1) described above.
E ²²¹ represents a substituent. Examples of the substituent represented by E ²²¹ include the groups exemplified for the substituent group Y.
m ²²¹ represents an integer of 2-5. As ^m221 , 2 or 3 is preferable.
m ²²² represents an integer of 0-3.
However, m ²²¹ +m ²²² represents an integer of 2-5.
* ⁴¹ represents the bonding position with X above.
* ⁴² represents the binding position with ^P4 above.

Among the groups represented by the above general formula (M1), groups represented by the following general formula (M2) are preferred.

In general formula (M2) above, X ²²³ , X ²²⁴ and X ²²⁵ each independently represent a single bond or a divalent linking group. The divalent linking group represented by X ²²³ , X ²²⁴ and X ²²⁵ is synonymous with the divalent linking group represented by L ¹ in general formula (B1) described above.
E ²²² and E ²²³ each independently represent a substituent. Examples of substituents represented by E ²²² and E ²²³ include the groups exemplified in Substituent Group Y.
m ²²³ represents an integer of 1-5. Among them, ^m223 is preferably 2 or 3.
m ²²⁴ represents an integer of 0-3.
m ²²⁵ represents an integer from 0 to 4.
m ²²⁶ represents an integer of 2-5. Among them, ^m226 is preferably 2 or 3.
However, m ²²⁴ +m ²²⁶ represents an integer of 2-5. Also, m ²²³ +m ²²⁵ represents an integer of 1-5.
* ⁴¹ represents the bonding position with X above.
* ⁴² represents the binding position with ^P4 above.

P ⁴ above has the same meaning as P ¹ in general formula (B1) above.
* ⁴ represents the bonding position with X above.

(Compound represented by general formula (V2))

In general formula (V2), X ¹¹ represents an n ¹¹ +n ¹² -valent organic group having a condensed ring structure containing two or more rings selected from the group consisting of aromatic hydrocarbon rings and aromatic heterocyclic rings.
X ¹¹ above represents an n ¹¹ +n ¹² -valent organic group (n ¹¹ and n ¹² are each independently an integer of 1 or more). n ¹¹ and n ¹² are each independently an integer of 1 or more and are not particularly limited. Although the upper limit of n ¹¹ +n ¹² is not particularly limited, it is preferably an integer of 15 or less. Among them, 2 to 8 are preferable, 2 to 3 are more preferable, and 2 is even more preferable in terms of better dispersibility of the surface-modified inorganic material.

Examples of the condensed ring structure containing two or more rings selected from the group consisting of an aromatic hydrocarbon ring and an aromatic heterocyclic ring in X ¹¹ include the structures described above, and preferred embodiments are also the same.

The n ¹¹ + n ^12- valent organic group represented by X ¹¹ is particularly limited as long as it has a condensed ring structure containing two or more rings selected from the group consisting of aromatic hydrocarbon rings and aromatic heterocycles. formed by abstracting n ¹¹ +n ¹² hydrogen atoms from a condensed ring containing two or more rings selected from the group consisting of aromatic hydrocarbon rings and aromatic heterocyclic rings, although the effect of the present invention is more excellent. is preferably a group.
The condensed structure may further have a substituent (for example, substituent group Y) in addition to Y ¹¹ and Y ¹² .

Y ¹¹ above includes a functional group selected from the following functional group group Q. Among the functional groups listed in the functional group group P described above, the functional groups listed in the functional group group Q below correspond to groups that tend to have excellent adsorptivity to inorganic substances (particularly inorganic nitrides).
Moreover, the above Y ¹² includes a functional group selected from the following functional group group R. Among the functional groups included in the functional group group P described above, the functional groups included in the functional group group R below correspond to groups having a function of facilitating curing of the composition.

(Functional group group Q)
Boronic acid group (-B(OH) ₂ ), aldehyde group (-CHO), isocyanate group (-N=C=O), isothiocyanate group (-N=C=S), cyanate group (-O-CN) , acyl azide group, succinimide group, sulfonyl chloride group (—SO ₂ Cl), carboxylic acid chloride group (—COCl), onium group, carbonate group (—O—CO—O—), aryl halide group, carbodiimide group ( -N=C=N-), an acid anhydride group (-CO-O-CO-, or monovalent acid anhydrides such as maleic anhydride, phthalic anhydride, pyromellitic anhydride, and trimellitic anhydride group), phosphonic acid group (-PO(OH) ₂ ), phosphinic acid group (-HPO(OH)), phosphate group (-OP(=O)(OH) ₂ ), phosphate ester group (-OP( =O) (OR ^B ) ₂ ), sulfonic acid group (-SO ₃ H), halogenated alkyl group, nitrile group (-CN), nitro group (-NO ₂ ), ester group (-CO-O- or - O—CO—), carbonyl group (—CO—), imidoester group (—C(=NR _C )—O— or —O—C(=NR _C )—), and halogen atom (fluorine atom, chlorine atom , a bromine atom, and an iodine atom).

(Functional group group R)
carboxylic acid group (-COOH), alkoxysilyl group, acrylic group (-OCOCH ₂ =CH ₂ ), methacrylic group (-OCOCH(CH ₃ )=CH ₂ ), oxetanyl group, vinyl group (-CH=CH ₂ ), Alkynyl group (group obtained by removing one hydrogen atom from alkyne. For example, ethynyl group and prop-2-yn-1-yl group are included.), maleimide group, thiol group (-SH), hydroxyl group (- OH), and functional groups selected from the group consisting of amino groups.

In the general formula (V2), the above Y ¹¹ specifically represents a monovalent group represented by the following general formula (C1) or a monovalent group represented by the following general formula (C2), or , n ¹¹ represents an integer of 2 or more, it represents a divalent group represented by the following general formula (C3) in which a plurality of Y ¹¹ are bonded.
In other words, when n ¹¹ is 1, Y ¹¹ above represents a monovalent group represented by the following general formula (C1) or a monovalent group represented by the following general formula (C2). When n ¹¹ represents an integer of 2 or more, does Y ¹¹ represent a monovalent group represented by the following general formula (C1) or a monovalent group represented by the following general formula (C2)? , or a divalent group represented by the following general formula (C3) in which a plurality of Y ¹¹ are bonded. In addition, when n ¹¹ is 2 or more, the plurality of Y ¹¹ may be the same or different.

When Y ¹¹ above represents a divalent group represented by general formula (C3) below, the compound represented by general formula (V2) is represented by general formula (V4) below.

X ¹¹ , Y ¹² and n ¹² in general formula (V4) are synonymous with X ¹¹ , Y ¹² and n ¹² in general formula (V2) described above. ^M3 has the same meaning as ^M3 in general formula (C3) described later.

General formula (C1): * ¹ -M ¹ -Q ¹
In general formula (C1), ^M1 represents a single bond or a divalent linking group. The divalent linking group represented by M ¹ has the same definition as L ¹ described above, and preferred embodiments are also the same.
The above Q ¹ is a monovalent organic group (boronic acid group (-B(OH) ₂ ), aldehyde group (-CHO), isocyanate group (-N=C=O), iso thiocyanate group (-N=C=S), cyanate group (-O-CN), acylazide group, succinimide group, sulfonyl chloride group (-SO ₂ Cl), carboxylic acid chloride group (-COCl), onium group, Aryl halide group, acid anhydride group (maleic anhydride, phthalic anhydride, pyromellitic anhydride, and monovalent acid anhydride groups such as trimellitic anhydride.), phosphonic acid group (-PO ( OH) ₂ ), phosphinic acid group (-HPO(OH)), phosphate group (-OP(=O)(OH) ₂ ), phosphate ester group (-OP(=O)(OR ^B ) ₂ ), sulfonic acid group (--SO ₃ H), halogenated alkyl group, nitrile group (--CN), nitro group (--NO ₂ ), or halogen atom (fluorine atom, chlorine atom, bromine atom and iodine atom)) show. * ¹ represents the bonding position with X ¹¹ above.

General formula (C2): * ² -M ² -Q ²
In general formula (B2), M ² has the same definition as L ² described above, and preferred embodiments are also the same. ^Q2 above represents a monovalent organic group. The monovalent linking group represented by Q ² has the same meaning as P ² described above, and preferred embodiments are also the same. * ² represents the bonding position with ^X11 above.

General formula (C3): * ³¹ -M ³ -* ³²
In general formula (B3), ^M3 has the same definition as ^L3 described above, and preferred embodiments are also the same. * ³¹ and * ³² represent the bonding positions with ^X11 above. That is, ^M3 above forms a ring together with two different carbon atoms on the condensed ring structure represented by ^X11 above.

Y ¹² above represents a monovalent group represented by the following general formula (D1) or a monovalent group represented by the following general formula (D2).
General formula (D1): * ¹ -W ¹ -R ¹
In general formula (D1), ^W1 represents a single bond or a divalent linking group. R ¹ represents a carboxylic acid group, an alkoxysilyl group, an acrylic group, a methacrylic group, an oxetanyl group, a vinyl group, an alkynyl group, a maleimide group, a thiol group, a hydroxyl group, or an amino group. * ¹ represents the bonding position with X ¹¹ above. R ¹ above represents a functional group listed in the functional group group R described above.
The divalent linking group represented by W ¹ has the same meaning as L ¹ described above, and preferred embodiments are also the same.
* ¹ represents the bonding position with X ¹¹ above.

General formula (D2):

In general formula (D2), W ² represents an m ²¹ + monovalent linking group.
^m21 represents an integer of 2 or more. Although the upper limit of ^m21 is not particularly limited, it is, for example, 100 or less, preferably 30 or less, more preferably 20 or less, and even more preferably 15 or less. Although the lower limit of ^m21 is not particularly limited, it is preferably 4 or more.
^R2 represents a carboxylic acid group, an alkoxysilyl group, an acrylic group, a methacrylic group, an oxetanyl group, a vinyl group, an alkynyl group, a maleimide group, a thiol group, a hydroxyl group, or an amino group. R ² above represents a functional group listed in the functional group group R described above.
The m ²¹ +1-valent linking group represented by W ² has the same meaning as L ⁴ described above, and preferred embodiments are also the same.
* ² represents the bonding position with ^X11 above.

The molecular weight of the surface modifier A is, for example, 150 or more, preferably 200 or more from the viewpoint of better dispersibility of the surface-modified inorganic nitride, and preferably 2,000 or less from the viewpoint of solubility. 000 or less is more preferable.

<Surface modifier B>
Also, the surface modifier is preferably the surface modifier B described below.
Surface modifier B is a compound represented by the following general formula (W1).

In general formula (W1), X represents a benzene ring group or a heterocyclic group which may have a substituent. That is, X represents an optionally substituted benzene ring group or an optionally substituted heterocyclic group.
Examples of the heterocyclic group include, but are not limited to, aliphatic heterocyclic groups and aromatic heterocyclic groups. The aliphatic heterocyclic group includes a 5-membered ring group, a 6-membered ring group, a 7-membered ring group, and condensed ring groups thereof. Moreover, the aromatic heterocyclic group includes a 5-membered ring group, a 6-membered ring group, a 7-membered ring group, or a condensed ring group thereof.
The condensed ring group may contain a ring group other than a heterocyclic group such as a benzene ring group.
Specific examples of the aliphatic heterocyclic group include, but are not particularly limited to, an oxolane ring group, an oxane ring group, a piperidine ring group, a piperazine ring group, and the like.

The heteroatom contained in the aromatic heterocyclic group includes, for example, a nitrogen atom, an oxygen atom, and a sulfur atom. The number of carbon atoms in the aromatic heterocyclic group is not particularly limited, but preferably 3-20.
Specific examples of the aromatic heterocyclic group are not particularly limited, but a furan ring group, a thiophene ring group, a pyrrole ring group, an oxazole ring group, an isoxazole ring group, an oxadiazole ring group, a thiazole ring group, and an isothiazole ring. group, thiadiazole ring group, imidazole ring group, pyrazole ring group, triazole ring group, furazane ring group, tetrazole ring group, pyridine ring group, pyridazine ring group, pyrimidine ring group, pyrazine ring group, triazine ring group, tetrazine ring group, benzofuran ring group, isobenzofuran ring group, benzothiophene ring group, indole ring group, indoline ring group, isoindole ring group, benzoxazole ring group, benzothiazole ring group, indazole ring group, benzimidazole ring group, quinoline ring group, isoquinoline ring group, cinnoline ring group, phthalazine ring group, quinazoline ring group, quinoxaline ring group, dibenzofuran ring group, dibenzothiophene ring group, carbazole ring group, acridine ring group, phenanthridine ring group, phenanthroline ring group, phenazine ring group , a naphthyridine ring group, a purine ring group, and a pteridine ring group.
The heterocyclic group represented by X is preferably an aromatic heterocyclic group.
Among them, X is preferably a benzene ring group or a triazine ring group, more preferably a triazine ring group.
When X has a substituent, the substituent preferably contains a specific functional group B described later.
In general formula (W1), n represents an integer of 3 to 6, and n groups represented by [-(L ¹ ) _m -Z] are bonded to X.

In general formula (W1), the group represented by [-(L ¹ ) _m -Z] is a group directly bonded to X.
L ¹ , which may be present in plurality, is each independently an optionally substituted arylene group, an ester group (-CO-O- or -O-CO-), an ether group (-O-), a thioester group ( -SO-O- or -O-SO-), thioether group (-S-), carbonyl group (-CO-), -NR ^N -, azo group (-N=N-), or represents an unsaturated hydrocarbon group.
R 3 ^N represents a hydrogen atom or an optionally substituted organic group having 1 to 10 carbon atoms.

The arylene group represented by L ₁ preferably has 6 to 20 carbon atoms, more preferably 6 to 10 carbon atoms, and still more preferably 6 carbon atoms. Among them, the arylene group is preferably a phenylene group.
When the above arylene group is a phenylene group, there are particular restrictions on the position where it bonds to adjacent groups (two groups out of X, L ₁ and Z, including the case where both groups are L ₁ ). may be bonded at any of the ortho-, meta-, and para-positions, preferably at the para-position. The arylene group may or may not have a substituent, preferably not. When the arylene group has a substituent, the substituent preferably contains a specific functional group B described later.
When L ₁ is an ester group, the carbon atoms in the ester group are preferably on the X side. When _L1 is a thioester group, the sulfur atom in the thioester group is preferably on the X side.
The unsaturated hydrocarbon group represented by L ₁ may be linear or branched, and may have a cyclic structure. The number of carbon atoms in the unsaturated hydrocarbon group is preferably 2-10, more preferably 2-5, still more preferably 2-3, and particularly preferably 2. However, the number of carbon atoms does not include the number of carbon atoms contained in the substituents that the unsaturated hydrocarbon group may have. The unsaturated bond of the unsaturated hydrocarbon group may be a double bond (-C=C-) or a triple bond (-C≡C-). The unsaturated hydrocarbon group may or may not have a substituent, preferably not. When the unsaturated hydrocarbon group has a substituent, the substituent preferably contains the specific functional group B.
When R ^N of —NR ^N — represented by L ₁ is an optionally substituted organic group having 1 to 10 carbon atoms, R ^N is optionally substituted carbon number It is preferably an alkyl group of 1 to 10 carbon atoms, preferably an optionally substituted alkyl group of 1 to 5 carbon atoms, an optionally substituted alkyl group of 1 to 3 carbon atoms is preferably a group. The alkyl group may be linear or branched, and may have a cyclic structure. ^RN is preferably a hydrogen atom.

m represents an integer of 0 or more. m is preferably an integer of 0 to 10, more preferably an integer of 0 to 5, still more preferably an integer of 0 to 2, and particularly preferably an integer of 1 to 2.
When m is 0, Z is directly bonded to X.
When m is 1, L ¹ is an optionally substituted arylene group, an ester group, an ether group, a thioester group, a thioether group, a carbonyl group, —NR ^N —, an azo group, or a substituent is preferably an unsaturated hydrocarbon group which may have a substituent, an arylene group which may have a substituent, an ester group, an ether group, a carbonyl group, or an unsaturated hydrocarbon group which may have a substituent and more preferably an ester group, an ether group, a carbonyl group, or an optionally substituted unsaturated hydrocarbon group.
When m is 2, [-(L ¹ ) _m -Z] is [-L ¹ -L ¹ -Z], and L ¹ bonded to X is an optionally substituted arylene group is preferred. In this case, L ¹ bonded to Z is an ester group, an ether group, a thioester group, a thioether group, a carbonyl group, —NR ^N —, an azo group, or an unsaturated hydrocarbon group which may have a substituent. is preferred, and an ester group or an optionally substituted unsaturated hydrocarbon group is more preferred.
When m is greater than 2, a plurality of L ^1s present in [-(L ¹ ) _m -Z] may be the same or different, but the L ^1s bonded to each other are preferably different.

—(L ¹ ) _m — in general formula (W1) is preferably a group represented by general formula (Lq). That is, the group represented by [-(L ¹ ) _m -Z] is preferably the group represented by [-L ^a -Z].
general formula (Lq) -L ^a -

L ^a is a single bond, -O-, -CO-, -COO-, phenylene group, -C=C-, -C≡C-, -phenylene group -COO-, or -phenylene group -C≡C - represents.

Z represents an aryl group or a heterocyclic group which may have a substituent. That is, Z represents an optionally substituted aryl group or an optionally substituted heterocyclic group.
The aryl group represented by Z preferably has 6 to 20 carbon atoms, more preferably 6 to 14 carbon atoms, and still more preferably 6 carbon atoms. Aryl groups include, for example, a phenyl group, a naphthyl group, an anthracenyl group, and the like.
As the heterocyclic group represented by Z, the same heterocyclic group that the above-mentioned X can be can be exemplified. Also, the heterocyclic group represented by Z preferably exhibits aromaticity.
Among them, Z is preferably an aryl group, more preferably a phenyl group or an anthracenyl group, and even more preferably a phenyl group.
Z preferably has a substituent, and more preferably the substituent contains a specific functional group B described later. The number of substituents that one Z has is preferably 0 to 5, more preferably 0 to 2, even more preferably 1 to 2.
It is preferable that at least one of the plurality of Zs has a substituent containing the specific functional group B.
The surface modifier B preferably has a total of 1 or more, more preferably 2 or more, and still more preferably 3 or more specific functional groups B contained in the plural substituents of Z.
The upper limit of the total number of specific functional groups B contained in a plurality of Z substituents of the surface modifier B is not particularly limited, but is preferably 15 or less, more preferably 10 or less, and even more preferably 8 or less.

As described above, n represents an integer of 3 to 6 in general formula (W1). Each group of a plurality of [-(L ¹ ) _m -Z] may be the same or different.
That is, in the general formula (W1), a plurality of m may be the same or different, and when a plurality of L ¹ are present, a plurality of L ¹ may be the same or different, and a plurality of Z are the same. but can be different.
It is also preferable that all of the multiple m's are the same. Moreover, it is preferable that each of the multiple m's represents an integer of 1 or more, and preferably represents an integer of 2 or more.
Plural [-(L ¹ ) _m -Z] preferably have the same configuration except for the substituent of Z, and preferably have the same configuration including the substituent of Z. .
n is preferably 3 or 6.
If a group that can be both (L ¹ ) _m and Z exists in [-(L ¹ ) _m -Z], then that group is (L ¹ ) _m . For example, when [-(L ¹ ) _m -Z] is [-benzene ring group-benzene ring group-halogen atom], the left benzene ring group is (L ¹ ) _m and not Z. More specifically, in the above case, "m = 1, L ¹ is a phenylene group (arylene group), and Z is a phenyl group (aryl group) having a halogen atom as a substituent", and "m = 0 and Z is not a phenyl group (aryl group) having an aryl halide group as a substituent.

Moreover, the surface modifier B represented by the general formula (W1) preferably has four or more benzene ring groups. For example, surface modifier B preferably has the structure of triphenylbenzene.
It is also preferable that the surface modifier B represented by general formula (W1) has a total of four or more benzene ring groups and triazine ring groups. In this case, for example, it is also preferred that X is a triazine ring group.

(Specific functional group B)
The surface modifier B preferably has one or more specific functional groups B, more preferably two or more.
The specific functional group B includes a boronic acid group, an aldehyde group, a hydroxyl group, a carboxylic acid group, an isocyanate group, an isothiocyanate group, a cyanate group, an acylazide group, a succinimide group, a sulfonyl chloride group, a carboxylic acid chloride group, an onium group, Carbonate group, aryl halide group, carbodiimide group, acid anhydride group (monovalent acid anhydride group), phosphonic acid group, phosphinic acid group, phosphoric acid group, phosphate ester group, sulfonic acid group, halogen atom, halogenation from alkyl groups, nitrile groups, nitro groups, imidoester groups, alkoxycarbonyl groups, alkoxysilyl groups, acryloyl groups, methacryloyl groups, oxetanyl groups, vinyl groups, alkynyl groups, maleimide groups, thiol groups, amino groups, and silyl groups It is a group selected from the group consisting of
Among them, the specific functional group B is preferably a hydroxyl group, an amino group, an acid anhydride group, a thiol group, a carboxylic acid group, an acryloyl group, a methacryloyl group, or a vinyl group.

Incidentally, the above hydroxyl group intends a group in which an —OH group is directly bonded to a carbon atom. For example, a --OH group present in a form included in a carboxylic acid group (--COOH) is not a hydroxyl group.
The alkoxycarbonyl group is not particularly limited as long as it is a group represented by —CO—OR ^f . The above R ^f represents an alkyl group (both linear, branched and cyclic).
The number of carbon atoms in the alkyl group represented by R ^f is, for example, 1 to 10, preferably 1 to 6, more preferably 1 to 3.
Moreover, among the specific functional groups B, the functional groups that overlap with the specific functional groups A are as described with respect to the specific functional groups A.

When the surface modifier B has a plurality of specific functional groups B, the plurality of specific functional groups B may be the same or different.
The position where the specific functional group B exists is not particularly limited. For example, the specific functional group B may be included in the substituents of X in the general formula (W1), and is an arylene group or an unsaturated hydrocarbon group. It may be included in the substituent of L ¹ in the case, and may be included in the substituent of Z.
In addition, the specific functional group B may be combined with a group other than the specific functional group B to form one substituent.
Further, a plurality of specific functional groups B may be contained in one substituent.

As the substituent containing the specific functional group B, a group represented by general formula (Rx), a group represented by general formula (Ry), or a group represented by general formula (Rz) is preferable.

general formula (Rx) -Lx ¹ -Qx
general formula (Ry)-Ly ¹ -Qy
general formula (Rz) -Lz ¹ -Sz-(Lz ² -Qz) _s

In general formula (Rx), Lx ¹ represents a single bond or a divalent linking group.
Although the divalent linking group is not particularly limited, for example, -O-, -CO-, -NH-, any one selected from the group consisting of divalent hydrocarbon groups, or a combination of two or more represents a valence linking group.
The divalent hydrocarbon group may further have a substituent (for example, the groups exemplified in Substituent Group Y).
Examples of the divalent hydrocarbon group include an alkylene group, an alkenylene group (e.g. -CH=CH-), an alkynylene group (e.g. -C≡C-), and an arylene group (e.g. phenylene group). mentioned. The alkylene group may be linear, branched, or cyclic, but is preferably linear. The number of carbon atoms is preferably 1-10, more preferably 1-6, and even more preferably 1-4.
Lx ¹ includes a single bond, -AL-, -O-, -O-CO-, -O-AL-, -AL-CO-, -O-AL-O-, -O-CO-AL-, -CO-O-AL-, -AL-NH-CO-, -O-AL-O-AL-, -CO-O-AL-O-, or -O-AL-O-Ar- is preferred.
AL represents an alkylene group having 1 to 10 carbon atoms (preferably 1 to 6 carbon atoms, more preferably 1 to 4 carbon atoms).
Ar above represents an arylene group having 6 to 20 carbon atoms (preferably a phenylene group). When Lx ¹ is "-O-AL-O-Ar-", Ar in "-O-AL-O-Ar-" bonds with Qx.
Qx represents a monovalent specific functional group B; Specifically, aldehyde group, hydroxyl group, carboxylic acid group, isocyanate group, isothiocyanate group, cyanate group, acylazide group, succinimide group, sulfonyl chloride group, carboxylic acid chloride group, onium group, aryl halide group, phosphonic acid group, phosphinic acid group, phosphoric acid group, sulfonic acid group, phosphate group, halogen atom, acid anhydride group, halogenated alkyl group, nitrile group, nitro group, alkoxycarbonyl group, alkoxysilyl group, acryloyl group, methacryloyl groups, oxetanyl groups, vinyl groups, alkynyl groups, maleimide groups, thiol groups, amino groups, epoxy groups, and silyl groups.

In general formula (Ry), Ly ¹ represents a divalent linking group containing a carbodiimide group, a carbonate group, or an imidoester group. The divalent linking group represented by Ly ¹ may contain a carbodiimide group, a carbonate group, or an imidoester group, and may be combined with other linking groups. Other linking groups include alkylene groups. For example, Ly ¹ may be an -alkylene group-Ly ³ -alkylene group-. Ly ³ represents a carbodiimide group, a carbonate group, or an imidoester group.
Qy above represents a monovalent organic group. The monovalent organic group represented by Qy is not particularly limited, and examples thereof include an alkyl group. The number of carbon atoms in the alkyl group is, for example, 1-10, preferably 1-6, more preferably 1-3.

In general formula (Rz), s represents an integer of 2-3. s is preferably 2.

Lz ¹ represents a group that can be represented by the above Lx ¹ , and preferred conditions are also the same.

Multiple Lz ^2s each independently represent a single bond or a divalent linking group.
Although the divalent linking group is not particularly limited, for example, any one or a combination of two or more selected from the group consisting of -O-, -CO-, -NH-, and divalent hydrocarbon groups represents a divalent linking group.
The divalent hydrocarbon group may further have a substituent (for example, the groups exemplified in Substituent Group Y).
Examples of the divalent hydrocarbon group include an alkylene group, an alkenylene group (e.g. -CH=CH-), an alkynylene group (e.g. -C≡C-), and an arylene group (e.g. phenylene group). mentioned. The alkylene group may be linear, branched, or cyclic, but is preferably linear. The number of carbon atoms is preferably 1-10, more preferably 1-6, and even more preferably 1-4.
Lz ² is a single bond, -AL-, -O-, -O-CO-, -O-AL-, -AL-CO-, -O-AL-O-, -O-CO-AL-, -CO-O-AL-, -AL-NH-CO-, -O-AL-O-AL-, -CO-O-AL-O-, -O-AL-O-Ar-, or -O -Ar- is preferred.
AL represents an alkylene group having 1 to 10 carbon atoms (preferably 1 to 6 carbon atoms, more preferably 1 to 4 carbon atoms).
Ar above represents an arylene group having 6 to 20 carbon atoms (preferably a phenylene group).

Sz represents a (s+1)-valent linking group.
Sz is preferably an (s+1)-valent aromatic ring group. The aromatic ring group may be either an aromatic hydrocarbon ring group or an aromatic heterocyclic ring group, preferably a benzene ring group or a triazine ring group.

Qz represents a monovalent specific functional group B;
Plural Qz's each independently represent a group that can be represented by the above Qx, and preferred conditions are also the same.

(Compound represented by general formula (W2))
Surface modifier B is preferably a compound represented by the following general formula (W2).

In general formula (W2), the definitions of La ^and Z are as described above. Plural L ^a 's may be the same or different. A plurality of Z's may be the same or different.

Each T independently represents -CR ^a = or -N=. R ^a represents a hydrogen atom, a monovalent specific functional group B, or -L ^a -Z. The definitions of ^La and Z are as described above.
For example, when all T are -CR ^a = and all R ^a are -L ^a -Z, the compound represented by general formula (W2) is represented by six -L ^a -Z has a group that is
Further, when all Ts are -N=, the compound represented by general formula (W2) has a triazine ring.

(Compound represented by general formula (W3))
As the compound represented by general formula (W2), a compound represented by general formula (W3) is preferable.

In general formula (W3), the definition of ^La is as described above. Plural L ^a 's may be the same or different.
Each Ar independently represents an aryl group. A preferred embodiment of the aryl group includes an aryl group represented by Z.
Each R ^b independently represents a substituent containing the specific functional group B. The definition of the specific functional group B is as described above. Moreover, as the substituent containing the specific functional group B, a group represented by the general formula (Rx), a group represented by the general formula (Ry), or a group represented by the general formula (Rz) is preferable.
p each independently represents an integer of 0 to 5; p is preferably 0-2. Among the three p's in general formula (W3), Aspect 1 in which two p's are 0 and one p is 1, or Aspect 2 in which all three p's are 1 is preferred.

In general formula (W3), each T ¹ independently represents -CR ^c = or -N=. R ^c represents a hydrogen atom, a monovalent specific functional group B, or -L ^a -Ar-(R ^b ) _p . The definitions of L ^a , Ar, R ^b and p are as described above.

The molecular weight of the surface modifier B is preferably 300 or more, more preferably 350 or more, from the viewpoint of better dispersibility of the surface-modified inorganic nitride. Moreover, the molecular weight of the surface modifier B is preferably 3000 or less, more preferably 2000 or less, from the viewpoint of excellent solubility.
Surface modifier B can be synthesized according to a known method.

<Other surface modifiers>
The composition also preferably contains an organosilane molecule (preferably a compound having an alkoxysilyl group) as a surface modifier (preferably when the inorganic material contains an inorganic oxide such as aluminum oxide). The organosilane molecules include surface modifier A, surface modifier B, and other surface modifiers that do not fall under any of these.
The other surface modifiers mentioned above are preferably used as surface modifiers for inorganic oxides, and more preferably used as surface modifiers for aluminum oxide.
Examples of organic silane molecules that are other surface modifiers include 3-aminopropyltriethoxysilane, 3-(2-aminoethyl)aminopropyltriethoxysilane, 3-aminopropyltrimethoxysilane, 3-(2 -aminoethyl)aminopropyltrimethoxysilane, N-phenyl-3-aminopropyltrimethoxysilane, 3-mercaptotriethoxysilane, and 3-ureidopropyltriethoxysilane.

One type of surface modifier may be used alone, or two or more types may be used.
When the composition contains a surface modifier, the content of the surface modifier is preferably 0.01 to 10% by mass, more preferably 0.10 to 5% by mass, based on the total inorganic matter.
The content of the inorganic nitride surface modifier (preferably surface modifier A and surface modifier B) is 0.01 to 10 with respect to all inorganic nitrides (preferably boron nitride and/or aluminum nitride) % by mass is preferred, and 0.10 to 5% by mass is more preferred.
The content of the organic silane molecule as the surface modifier (preferably the organic silane molecule as another surface modifier) is preferably 0.01 to 10% by mass with respect to the total inorganic oxide (preferably aluminum oxide). , 0.10 to 5 mass % is more preferred.

[Curing accelerator]
The composition may further contain a curing accelerator.
The type of curing accelerator is not limited, and examples thereof include triphenylphosphine, boron trifluoride amine complex, and compounds described in paragraph 0052 of JP-A-2012-67225. In addition, 2-methylimidazole (trade name; 2MZ), 2-undecylimidazole (trade name; C11-Z), 2-heptadecylimidazole (trade name; C17Z), 1,2-dimethylimidazole (trade name) ; 1.2DMZ), 2-ethyl-4-methylimidazole (trade name; 2E4MZ), 2-phenylimidazole (trade name; 2PZ), 2-phenyl-4-methylimidazole (trade name; 2P4MZ), 1-benzyl -2-methylimidazole (trade name; 1B2MZ), 1-benzyl-2-phenylimidazole (trade name; 1B2PZ), 1-cyanoethyl-2-methylimidazole (trade name; 2MZ-CN), 1-cyanoethyl-2- undecylimidazole (trade name; C11Z-CN), 1-cyanoethyl-2-phenylimidazolium trimellitate (trade name; 2PZCNS-PW), 2,4-diamino-6-[2'-methylimidazolyl-(1 ')]-ethyl-s-triazine (trade name; 2MZ-A), 2,4-diamino-6-[2'-undecylimidazolyl-(1')]-ethyl-s-triazine (trade name; C11Z -A), 2,4-diamino-6-[2′-ethyl-4′-methylimidazolyl-(1′)]-ethyl-s-triazine (trade name; 2E4MZ-A), 2,4-diamino- 6-[2′-methylimidazolyl-(1′)]-ethyl-s-triazineisocyanuric acid adduct (trade name; 2MA-OK), 2-phenyl-4,5-dihydroxymethylimidazole (trade name; 2PHZ- PW), 2-phenyl-4-methyl-5-hydroxymethylimidazole (trade name; 2P4MHZ-PW), and 1-cyanoethyl-2-phenylimidazole (trade name; 2PZ-CN) and other imidazole curing accelerators etc. (both manufactured by Shikoku Kasei Co., Ltd.).
A single curing accelerator may be used alone, or two or more curing accelerators may be used.
The content of the curing accelerator is preferably 0.01 to 10% by mass, more preferably 0.10 to 5% by mass, based on the total epoxy compound.

[Dispersant]
The composition may further contain a dispersing agent.
When the composition contains a dispersant, the dispersibility of the inorganic material in the composition containing the epoxy compound and the phenolic compound is improved, and superior thermal conductivity and adhesion can be achieved.

The dispersant can be appropriately selected from commonly used dispersants. For example, DISPERBYK-106 (manufactured by BYK-Chemie GmbH), DISPERBYK-111 (manufactured by BYK-Chemie GmbH), ED-113 (manufactured by Kusumoto Kasei Co., Ltd.), Ajisper PN-411 (manufactured by Ajinomoto Fine Techno), and REB122- 4 (manufactured by Hitachi Chemical Co., Ltd.) and the like.
A dispersant may be used individually by 1 type, and may use 2 or more types.
The content of the dispersant is preferably 0.01 to 10% by mass, more preferably 0.1 to 5% by mass, based on the total inorganic matter.

〔solvent〕
The composition may further contain a solvent.
The type of solvent is not particularly limited, and an organic solvent is preferred. Examples of organic solvents include cyclopentanone, cyclohexanone, ethyl acetate, methyl ethyl ketone, dichloromethane, and tetrahydrofuran.
When the composition contains a solvent, the content of the solvent is preferably an amount that makes the solid content concentration of the composition 20 to 90% by mass, more preferably 30 to 85% by mass, and 40 to 85% by mass. is more preferable, and an amount of 50 to 80% by mass is particularly preferable.

[Method for producing composition]
A method for producing the composition is not particularly limited, and a known method can be employed. For example, the composition can be produced by mixing the various components described above. When mixing, various components may be mixed together or may be mixed sequentially.
There is no particular limitation on the method of mixing the components, and known methods can be used. The mixing device used for mixing is preferably a submerged disperser. and a homogenizer. One type of mixing device may be used alone, or two or more types may be used. Degassing may be performed before, after and/or at the same time as mixing.

[Method of curing composition]
The thermally conductive material of the present invention is obtained by curing the composition of the present invention.
A method for curing the composition is not particularly limited, but a thermosetting reaction is preferred.
The heating temperature during the thermosetting reaction is not particularly limited. For example, the temperature may be appropriately selected within the range of 50 to 250°C. Moreover, when performing a thermosetting reaction, heat treatment at different temperatures may be performed a plurality of times.
The curing treatment is preferably carried out on the composition in the form of a film or sheet. Specifically, for example, the composition may be applied to form a film, followed by a curing reaction.
When the curing treatment is performed, it is preferable to apply the composition on the substrate to form a coating film and then cure the composition. 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.
In addition, when performing the curing treatment, the composition may be applied on separate substrates to form coating films, respectively, and the curing treatment may be performed in a state in which the obtained coating films are brought into 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.
Pressing may be performed during the hardening treatment. The press used for pressing is not limited, and for example, a flat plate press or a roll press may be used.
When using a roll press, for example, a substrate with a coating film obtained by forming a coating film on the substrate is sandwiched between a pair of rolls facing each other, and the pair of rolls is sandwiched. It is preferable to apply pressure in the film thickness direction of the substrate with the coating film while rotating to pass the substrate with the coating film. The base material with the coating film may have the base material on only one side of the coating film, or may have the base material on both sides of the coating film. The coated substrate may be passed through the roll press only once or may be passed multiple times.
Either one or both of the treatment by flat press and the treatment by roll press may be carried out.

Moreover, the curing treatment may be terminated when the composition is in a semi-cured state. After the semi-cured thermally conductive material of the present invention is placed in contact with a device or the like to be used, curing may be further advanced by heating or the like to be fully cured. It is also preferable that the device and the thermally conductive material of the present invention are adhered by heating or the like during the final curing.
For the preparation of thermally conductive materials including curing reactions, reference can be made to "Highly Thermally Conductive Composite Materials" (by Yoshitaka Takezawa, published by CMC Publishing).

There are no particular restrictions on the shape of the heat-conducting material, and it can be molded into various shapes depending on the application. A typical shape of the molded thermally conductive material includes, for example, a sheet shape.
That is, the thermally conductive material of the present invention is also preferably a thermally conductive sheet.
Also, the thermal conductivity of the thermally conductive material of the present invention is preferably isotropic rather than anisotropic.

Preferably, the thermally conductive material is insulating (electrically insulating). In other words, the compositions of the present invention are preferably thermally conductive insulating compositions.
For example, the volume resistivity of the heat conductive material at 23° C. and 65% relative humidity is preferably 10 ¹⁰ Ω·cm or more, more preferably 10 ¹² Ω·cm or more, and still more preferably 10 ¹⁴ Ω·cm or more. Although the upper limit is not particularly limited, it is usually 10 ¹⁸ Ω·cm or less.

[Applications of thermally conductive materials]
The thermally conductive material 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 of various devices. More specifically, a heat conductive layer containing the heat conductive material of the present invention is arranged on a device to produce a device with a heat conductive layer, and heat generated from the device can be efficiently radiated by the heat conductive layer.
Since the thermally conductive material of the present invention has sufficient thermal conductivity and high heat resistance, it is used in power semiconductor devices used in various electrical equipment such as personal computers, general home appliances, and automobiles. Suitable for heat dissipation applications.
Furthermore, since the thermally conductive material of the present invention has sufficient thermal conductivity even in a semi-cured state, it can be used in areas where light for photocuring is difficult to reach, such as gaps between members of various devices. It can also be used as a heat dissipating material to be placed. Moreover, since it is excellent in adhesiveness, it can be used as an adhesive having thermal conductivity.

The thermally conductive material of the present invention may be used in combination with members other than members formed from the present composition.
For example, a sheet-like thermally conductive material (thermally-conductive sheet) may be combined with a sheet-like support other than the layer formed from the present composition.
Sheet-like supports include plastic films, metal films, and glass plates. Examples of plastic film materials include polyesters such as polyethylene terephthalate (PET), polycarbonates, acrylic resins, epoxy resins, polyurethanes, polyamides, polyolefins, cellulose derivatives, and silicones. Metal films include copper films.
The film thickness of the sheet-like thermally conductive material (thermally conductive sheet) is preferably 100 to 300 μm, more preferably 150 to 250 μm.

The present invention will be described in more detail based on examples below. The materials, amounts used, proportions, processing details, processing procedures, etc. shown in the following examples can be changed as appropriate without departing from the gist of the present invention. Therefore, the scope of the present invention should not be construed as limited by the examples shown below.

[Preparation and Evaluation of Composition]
[Various components]
Various components used in Examples and Comparative Examples are shown below.
<Phenol compound>
Phenolic compounds used in Examples and Comparative Examples are shown below.

<Epoxy compound>
The epoxy compounds used in Examples and Comparative Examples are shown below.
B-5 below is a mixture of two types of epoxy compounds (trade name: Epotato ZX-1059, manufactured by Tohto Kasei Co., Ltd.).

<Inorganic matter>
Inorganic substances used in Examples and Comparative Examples are shown below.
“PTX-60”: aggregated boron nitride (average particle size: 60 μm, manufactured by Momentive)
“PT-110”: Tabular boron nitride (average particle size: 45 μm, manufactured by Momentive)
"AA-3": aluminum oxide (average particle size: 3 μm, manufactured by Sumitomo Chemical)
"AA-04": aluminum oxide (average particle size: 0.4 μm, manufactured by Sumitomo Chemical)
“S-50”: aluminum nitride (average particle size: 55 μm, manufactured by MARUWA)
“HP40 MF100”: aggregated boron nitride (average particle size: 40 μm, made by Mizushima ferroalloy)

<Curing accelerator>
The curing accelerators used in Examples and Comparative Examples are shown below.
"TPP": triphenylphosphine "2PZ-CN": 1-cyanoethyl-2-phenylimidazole (manufactured by Shikoku Kasei Kogyo)
"2PHZ-PW": 2-phenyl-4,5-dihydroxymethylimidazole (manufactured by Shikoku Chemical Industry)

<Solvent>
Cyclopentanone was used as solvent.

<Dispersant>
DISPERBYK-106 (a polymer salt having an acidic group) was used as a dispersant.

<Surface treatment agent for aluminum oxide (organosilane molecule)>
The following compounds were used as surface modifiers for aluminum oxide.

<Surface Modifier for Inorganic Nitride>
Inorganic nitride surface modifiers used in Examples and Comparative Examples are shown below.

[Preparation of composition]
A curing liquid was prepared by blending the epoxy compound and the phenol compound in the combinations shown in Table 1 below in an equivalent amount (an amount that makes the number of epoxy groups of the epoxy compound equal to the number of hydroxyl groups of the phenol compound).
After the curing liquid, solvent, dispersant, surface modifier (aluminum oxide surface modifier, inorganic nitride surface modifier) and curing accelerator were mixed in this order, an inorganic material was added. The resulting mixture was processed for 5 minutes in a rotation-revolution mixer (Awatori Mixer ARE-310, manufactured by THINKY) to obtain a composition (composition for forming a heat conductive material) of each example or comparative example.

Here, the amount of solvent added was such that the solid content concentration of the composition was 50 to 80% by mass.
The solid content concentration of the composition was adjusted for each composition within the above range so that the viscosities of the compositions were approximately the same.
The amount of the curing accelerator added was such that the content of the curing accelerator in the composition was 1% by mass with respect to the content of the epoxy compound. Table 1 shows the types of curing accelerators used.
The amount of inorganic substances added (total of all inorganic substances) was such that the content of inorganic substances in the composition became the value (% by mass) shown in Table 1 with respect to the total solid content of the composition.
In addition, the inorganic substances were mixed and used so that the content ratio (mass ratio) of each inorganic substance satisfies the relationship shown in Table 1.
The amount of the dispersant added was such that the content of the dispersant in the composition was 0.2% by mass with respect to the content of the inorganic substance.
The amount of the surface modifier for aluminum oxide to be added is such that the content of the surface modifier for aluminum oxide in the composition is 0.2 with respect to the content of aluminum oxide (total content of AA-3 and AA04). The amount was set to be the mass %. When the composition does not contain aluminum oxide, no surface modifier for aluminum oxide is used.
When the inorganic nitride surface modifier is used, the amount of the inorganic nitride surface modifier added is such that the content of the inorganic nitride surface modifier in the composition is equal to the content of the inorganic nitride (PTX-60 , PT-110, HP-40, MF100, and S-50), the amount was 0.3% by mass.

[evaluation]
<Thermal conductivity>
Using an applicator, the prepared composition is uniformly applied on the release surface of a release-treated polyester film (NP-100A manufactured by Panac, film thickness 100 μm), and left at 120 ° C. for 5 minutes to form a coating film. got
Two such polyester films with a coating film are prepared, and the two polyester films with a coating film are laminated to each other on the coating film surfaces, and then hot pressed under air (hot plate temperature 65 ° C., pressure 12 MPa, 1 minutes) to obtain a semi-cured film. The resulting semi-cured film is hot-pressed in air (hot plate temperature 160° C., pressure 12 MPa for 20 minutes, and then under normal pressure 180° C. for 90 minutes) to cure the coating film and form a resin sheet. got The polyester films on both sides of the resin sheet were peeled off to obtain a thermally conductive sheet with an average thickness of 200 µm.

Thermal conductivity evaluation was performed using each thermally conductive sheet obtained using each composition. Thermal conductivity was measured by the following method, and thermal conductivity was evaluated according to the following criteria.

(Measurement of thermal conductivity (W/m·k))
(1) Using "LFA467" manufactured by NETZSCH, the thermal diffusivity in the thickness direction of the thermally conductive sheet was measured by the laser flash method.
(2) Using a balance "XS204" manufactured by Mettler Toledo, the specific gravity of the thermally conductive sheet was measured by the Archimedes method (using the "solid specific gravity measurement kit").
(3) Using "DSC320/6200" manufactured by Seiko Instruments Inc., the specific heat of the thermally conductive sheet at 25°C was determined under the condition of temperature increase of 10°C/min.
(4) The obtained thermal diffusivity was multiplied by the specific gravity and the specific heat to calculate the thermal conductivity of the thermally conductive sheet.

(Evaluation criteria)
The measured thermal conductivity was classified according to the following criteria, and the thermal conductivity was evaluated.
"A+": 15 W/m·K or more "A": 10 W/m·K or more and less than 15 W/m·K "B": 8 W/m·K or more and less than 10 W/m·K "C": 5 W/m·K or more K or more and less than 8 W/m·K “D”: Less than 5 W/m·K The results are shown in Table 1.

<Insulation>
The volume resistance value at 23° C. and 65% relative humidity of the thermally conductive sheet produced in the same manner as in the above evaluation of “thermal conductivity” was measured using Hiresta MCP-HT450 type (manufactured by Mitsubishi Chemical Analytech Co., Ltd.). It was measured.

(Evaluation criteria)
The measured thermally conductive sheet volume resistance value was classified according to the following criteria, and the insulating properties were evaluated.
"A": 10 ¹⁴ Ω·cm or more "B": 10 ¹² Ω·cm or more and less than 10 ¹⁴ Ω·cm "C": 10 ¹⁰ Ω·cm or more and less than 10 ¹² Ω·cm "D": 10 ¹⁰ Ω·cm less than cm

[result]
Table 1 is shown below.
In Table 1, the "Structure" column in the "Phenol compound" column shows the structure of the phenol compound used. "S1" means that the phenol compound is a compound represented by general formula (1). "S" means that the phenol compound is a spirophenol compound other than the compound represented by general formula (1). "-" means that the phenolic compound is not a spirophenolic compound.
The "structure" column in the "epoxy compound" column shows the structure of the epoxy compound used. "S1" means that the epoxy compound is a compound represented by general formula (1E). "-" means that the epoxy compound is not a spiroepoxy compound.
The column of "number of functional groups" indicates the hydroxyl group content (mmol/g) of the phenol compound used.
The column of "type of surface modifier" indicates whether or not an inorganic nitride surface modifier is used, and the type of the inorganic nitride surface modifier used when the inorganic nitride surface modifier is used.

From the results shown in the table, it was confirmed that a thermally conductive material having excellent thermal conductivity can be obtained by using the composition of the present invention. Moreover, it was confirmed that the thermally conductive material is also excellent in insulating properties.

It has been confirmed that the thermal conductivity of the resulting thermally conductive material is superior when the composition contains boron nitride.
(Comparison between Example 2 and Example 22, etc.)

It has been confirmed that when the spirophenol compound is a compound represented by the general formula (1), the thermal conductivity and/or insulation properties of the obtained thermally conductive material are superior.
(Examples 212 to 307, comparison with other examples, etc.)

It has been confirmed that when the molecular weight of the spirophenol compound is 400 or less, the resulting thermally conductive material has more excellent insulating properties.
(Example using phenolic compound A-3 and comparison with examples using phenolic compounds A-1, A-2, and A-4 (example using compound represented by general formula (1) comparison) etc.)

It was confirmed that when the hydroxyl group content of the spirophenol compound is 6.5 mmol/g or more, the thermal conductivity and/or insulating properties of the obtained thermally conductive material are more excellent.
(Examples using phenolic compounds A-2, A-3, A-4 and comparison with examples using phenolic compound A-1 (Examples using the compound represented by the general formula (1) Comparison between each other), comparison between examples using phenol compound A-6 and examples using phenol compound A-5 (implementation using a spirophenol compound other than the compound represented by the general formula (1) comparison between examples), etc.)

It was confirmed that when a compound having a condensed ring skeleton or a triazine skeleton is used as the surface modifier, the thermal conductivity of the resulting thermally conductive material is more excellent (Examples 1, 5 to 8, 10 to 12, 14 to 19 results, etc.).

Claims (11)

A composition for forming a thermally conductive material containing a phenolic compound, an epoxy compound, and an inorganic substance,
The phenol compound comprises a spirophenol compound having a phenolic hydroxyl group and a spiro structure,
The epoxy compound satisfies at least one of an epoxy group and a spiro epoxy compound having a spiro structure,
The phenol compound contains a spirophenol compound represented by the general formula (1),
A composition for forming a heat conductive material , wherein the spirophenol compound has a hydroxyl group content of 10.8 mmol/g or more .

In general formula (1), ns1 and ns2 each independently represent an integer of 1-4.
A ^S and D ^S each independently represent -CR ^Sx R ^Sy -, -O-, or -S-.
R ^Sx and R ^Sy each independently represent a hydrogen atom or a substituent.
R ^SA , R ^SB , R ^SC and R ^SD each independently represent a hydrogen atom, an alkyl group or an aryl group. 2. The composition for forming a thermally conductive material according to claim 1 , comprising said spirophenol compound, said spirophenol compound being a compound represented by general formula (2).

In general formula (2), ns1 and ns2 each independently represent an integer of 1-4.
R ^SA , R ^SB , R ^SC and R ^SD each independently represent a hydrogen atom, an alkyl group or an aryl group. 3. The composition for forming a thermally conductive material according to claim 1 , wherein the spirophenol compound has a molecular weight of 400 or less. The composition for forming a thermally conductive material according to any one of claims 1 to 3 , wherein the inorganic substance includes an inorganic nitride. 5. The composition for forming a thermally conductive material according to claim 4 , wherein said inorganic nitride comprises boron nitride. The composition for forming a thermally conductive material according to any one of claims 1 to 5 , further comprising the inorganic surface modifier. 7. The composition for forming a thermally conductive material according to claim 6 , wherein said surface modifier has a condensed ring skeleton or a triazine skeleton. The composition for forming a thermally conductive material according to any one of claims 1 to 7 , further comprising a curing accelerator. A thermally conductive material obtained by curing the composition for forming a thermally conductive material according to any one of claims 1 to 8 . A thermally conductive sheet made of the thermally conductive material according to claim 9 . A device with a thermally conductive layer, comprising: a device; and a thermally conductive layer comprising the thermally conductive sheet according to claim 10 disposed on the device.