Epoxy resin compositions, compositions for electronic components, materials for electronic components

Abstract

To provide an epoxy resin composition having high thermal conductivity and high heat resistance and to provide a composition which provides a cured product of the epoxy resin.SOLUTION: There is provided a composition which comprises at least one of A component as an epoxy compound and B component as a curing agent in a composition comprising an epoxy compound and a curing agent. A component: a compound having two or more oxiranyls and two to five aromatic rings in which one to three hydrogens in the aromatic ring are replaced by vinyl-derived groups. B component: a compound having two or more phenolic hydroxy groups in which the hydroxy groups have an acylated group or two or more cyanate esters and two to five aromatic rings in which one to three hydrogens in the aromatic ring are replaced by vinyl-derived groups.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a composition for electronic parts that efficiently conducts heat generated inside an electronic device, and to a polymerizable compound having liquid crystal properties used therein. [Background technology]

[0002] In recent years, there has been a demand for packaging materials with high thermal conductivity to prevent the temperature of the internal semiconductors from becoming too high in semiconductor elements used in power control in hybrid and electric vehicles, CPUs for high-speed computers, etc. In other words, the ability to effectively dissipate heat generated by the semiconductor chip to the outside has become important.

[0003] One way to solve this heat dissipation problem is to contact the heat-generating area with a highly thermally conductive material (heat dissipation component) to guide the heat to the outside and dissipate it. Materials with high thermal conductivity include inorganic materials such as metals and metal oxides. However, these inorganic materials have problems with processability and insulation, making them very difficult to use alone as fillers for semiconductor packages. For this reason, efforts are underway to develop heat dissipation components with high thermal conductivity that combine these inorganic materials with resins.

[0004] Increasing the thermal conductivity of composite materials has generally been achieved by adding large amounts of inorganic fillers, such as metal fillers, to general-purpose resins such as polyethylene resin, polyamide resin, polystyrene resin, acrylic resin, and epoxy resin. However, the thermal conductivity of inorganic fillers is a substance-specific value with a set upper limit. Therefore, methods to achieve this by improving the thermal conductivity of the resin have been widely attempted. One known method for achieving this is to use an epoxy compound with liquid crystal properties.

[0005] Patent Document 1 discloses a terphenyl compound having two glycidyloxy groups. Patent Document 2 discloses a terphenyl compound having three glycidyloxy groups. However, the compounds disclosed in these patent documents do not have a liquid crystal temperature and have a high melting point of 117°C or higher. [Prior art documents] [Patent documents]

[0006] [Patent Document 1] International Publication No. 2005 / 61473 [Patent Document 2] International Publication No. 2016 / 6649 Summary of the Invention [Problem to be solved by the invention]

[0007] An object of the present invention is to provide an epoxy resin having high thermal conductivity and heat resistance, and an epoxy resin composition that provides such an epoxy resin. [Means for solving the problem]

[0008] The present inventors have discovered that a composition containing at least one of component A as an epoxy compound and component B as a curing agent, and a cured product thereof, can solve the above-mentioned problems, and have completed the present invention.

[0009] Component A: a compound having two or more oxiranyl groups and 2 to 5 aromatic rings, in which 1 to 3 hydrogen atoms of the aromatic rings have been replaced with groups derived from vinyl. Component B: A compound having two or more phenolic hydroxyl groups or two or more cyanate esters and having two to five aromatic rings, in which one to three hydrogen atoms of the aromatic rings have been replaced with groups derived from vinyl. [Effects of the Invention]

[0010] The composition itself or upon curing tends to exhibit liquid crystallinity. As a result, the cured product has high thermal conductivity and high heat resistance. Therefore, it can be suitably used as a heat dissipation material for power semiconductors and the like. DETAILED DESCRIPTION OF THE INVENTION

[0011] Hereinafter, embodiments of the present invention will be described in detail, but the present invention is not limited to the embodiments.

[0012] The present invention includes the following items.

[0013] [1] A composition containing an epoxy compound and a curing agent, the composition containing at least one of component A as an epoxy compound and component B as a curing agent. Component A: a compound having two or more oxiranyl groups and 2 to 5 aromatic rings, in which 1 to 3 hydrogen atoms of the aromatic rings have been replaced with groups derived from vinyl. Component B: A compound having two or more phenolic hydroxyl groups, groups in which the hydroxyl groups are acylated, or two or more cyanate esters, and having two to five aromatic rings, in which one to three hydrogen atoms of the aromatic rings have been replaced with groups derived from vinyl.

[0014] [2] The composition according to item [1], wherein component A or component B is a compound having a skeleton in which aromatic rings are linearly connected.

[0015] [3] The composition according to item [2], containing component A, wherein component A is a compound represented by formula (A). TIFF0007725880000001.tif32139 In formula (A), R ep are independently a group having 3 to 12 carbon atoms, including oxiranyl; X is independently a single bond, alkylene having 1 to 12 carbon atoms, -CHO-, -CH=CH-, or -C≡C-; R 1 At least one of R is a group represented by formula (1), and the other R 1 are independently hydrogen, alkyl having 1 to 5 carbon atoms, or alkoxy having 1 to 5 carbon atoms; n is an integer from 0 to 2. TIFF0007725880000002.tif2548 In formula (1), R 2are independently hydrogen or alkyl having 1 to 12 carbon atoms, and * indicates the bonding position to the aromatic ring.

[0016] [4] The composition according to item [2], containing component B, wherein component B is a compound represented by formula (BI). TIFF0007725880000003.tif32135 formula (BI), X is independently a single bond, alkylene having 1 to 12 carbon atoms, -CHO-, -CH=CH-, or -C≡C-; R 1 At least one of R is a group represented by formula (1), and the other R 1 are independently hydrogen, alkyl having 1 to 5 carbon atoms, or alkoxy having 1 to 5 carbon atoms; n is an integer from 0 to 2. TIFF0007725880000004.tif2648 In formula (1), R 2 are independently hydrogen or alkyl having 1 to 12 carbon atoms, and * indicates the bonding position to the aromatic ring.

[0017] [5] The composition according to item [2], containing component B, wherein component B is a compound represented by formula (B-II). TIFF0007725880000005.tif32145 formula (B-II), X is independently a single bond, alkylene having 1 to 12 carbon atoms, -CHO-, -CH=CH-, or -C≡C-; R 1 At least one of R is a group represented by formula (1), and the other R 1 are independently a group represented by hydrogen, alkyl having 1 to 5 carbon atoms, or alkoxy having 1 to 5 carbon atoms, R 3 are independently alkyl having 1 to 6 carbon atoms or phenyl, n is an integer from 0 to 2. TIFF0007725880000006.tif2648 In formula (1), R 2 are independently hydrogen or alkyl having 1 to 12 carbon atoms, and * indicates the bonding position to the aromatic ring.

[0018] [6] The composition according to [2], which contains component B, and component B is a compound represented by formula (B-III). TIFF0007725880000007.tif32141 formula (B-III), X is independently a single bond, alkylene having 1 to 12 carbon atoms, -CHO-, -CH=CH-, or -C≡C-; R 1 At least one of R is a group represented by formula (1), and the other R 1 are independently a group represented by hydrogen, alkyl having 1 to 5 carbon atoms, or alkoxy having 1 to 5 carbon atoms, n is an integer from 0 to 2. TIFF0007725880000008.tif2648In formula (1), R 2 are independently hydrogen or alkyl having 1 to 12 carbon atoms, and * indicates the bonding position to the aromatic ring.

[0019] [7] The composition according to item [3], wherein in the compound represented by formula (A), X is a single bond or -C≡C-.

[0020] [8] The composition according to item [4], wherein in the compound represented by formula (BI), X is a single bond or -C≡C-.

[0021] [9] The composition according to item [5], wherein in the compound represented by formula (B-II), X is a single bond or -C≡C-.

[0022]

[10] The composition according to item [6], wherein in the compound represented by formula (B-III), X is a single bond or -C≡C-.

[0023]

[11] The composition according to any one of items [1] to

[10] , further comprising a curing accelerator.

[0024]

[12] The composition according to item

[11] , further comprising an inorganic filler.

[0025]

[13] The composition according to item

[12] , wherein the inorganic filler is aluminum oxide, boron nitride, or aluminum nitride.

[0026]

[14] A cured product obtained by curing the composition according to any one of items [1] to

[13] .

[0027]

[15] A material for electronic components using the cured product of item

[14] .

[0028]

[16] A compound represented by formula (A1): TIFF0007725880000009.tif32142 formula (A1), R ep are independently a group having 3 to 12 carbon atoms, including oxiranyl; X is independently a single bond, alkylene having 1 to 12 carbon atoms, -CHO-, -CH=CH-, or -C≡C-; R 1 At least one of R is a group represented by formula (1), and the other R 1 are independently hydrogen, alkyl having 1 to 5 carbon atoms, or alkoxy having 1 to 5 carbon atoms; n is an integer from 0 to 2. TIFF0007725880000010.tif2548 In formula (1), R 2 are independently hydrogen or alkyl having 1 to 12 carbon atoms, and * indicates the bonding position to the aromatic ring.

[0029]

[17] A compound represented by formula (B1): TIFF0007725880000011.tif32135 formula (B1), X is independently a single bond, alkylene having 1 to 12 carbon atoms, -CHO-, -CH=CH-, or -C≡C-; R 1 At least one of R is a group represented by formula (1), and the other R 1 are independently hydrogen, alkyl having 1 to 5 carbon atoms, or alkoxy having 1 to 5 carbon atoms; n is an integer from 0 to 2. TIFF0007725880000012.tif2648 In formula (1), R 2 are independently hydrogen or alkyl having 1 to 12 carbon atoms, and * indicates the bonding position to the aromatic ring. However, the compound represented by formula (B1) is not a compound represented by formula (B1-1). TIFF0007725880000013.tif21113

[0030]

[18] A compound represented by formula (B2): TIFF0007725880000014.tif32143 formula (B2), X is independently a single bond, alkylene having 1 to 12 carbon atoms, -CHO-, -CH=CH-, or -C≡C-; R 1 At least one of R is a group represented by formula (1), and the other R 1 are independently hydrogen, alkyl having 1 to 5 carbon atoms, or alkoxy having 1 to 5 carbon atoms; R 3 are independently alkyl having 1 to 6 carbon atoms or phenyl, n is an integer from 0 to 2. TIFF0007725880000015.tif2648 In formula (1), R 2 are independently hydrogen or alkyl having 1 to 12 carbon atoms, and * indicates the bonding position to the aromatic ring.

[0031]

[19] A compound represented by formula (B3): TIFF0007725880000016.tif32138 In formula (B3), X is independently a single bond, alkylene having 1 to 12 carbon atoms, -CHO-, -CH=CH-, or -C≡C-; R 1 At least one of R is a group represented by formula (1), and the other R 1 are independently hydrogen, alkyl having 1 to 5 carbon atoms, or alkoxy having 1 to 5 carbon atoms; n is an integer from 0 to 2. TIFF0007725880000017.tif2648 In formula (1), R 2 are independently hydrogen or alkyl having 1 to 12 carbon atoms, and * indicates the bonding position to the aromatic ring.

[0032]

[20] In the compound represented by formula (A1), R ep are independently a group having 3 to 12 carbon atoms including oxiranyl, X is a single bond, and R 1 One of R is a group represented by formula (1), and the other R 1 is hydrogen, and n is an integer of 0 or 1.

[0033]

[21] In the compound represented by formula (B1), X is a single bond and R 1 One of R is a group represented by formula (1), and the other R 1 is hydrogen, and n is an integer of 0 or 1.

[0034]

[22] In the compound represented by formula (B2), X is a single bond and R 1 One of R is a group represented by formula (1), and the other R 1 is hydrogen, and n is an integer of 0 or 1.

[0035]

[23] In the compound represented by formula (B3), X is a single bond and R 1 One of R is a group represented by formula (1), and the other R 1 is hydrogen, and n is an integer of 0 or 1.

[0036] The phrase "at least one hydrogen atom in the ring may be replaced by alkyl having 1 to 10 carbon atoms" means, for example, an embodiment in which at least one hydrogen atom at the 2-, 3-, 5-, and 6-positions of 1,4-phenylene is replaced by a substituent such as fluorine or methyl. "Compound (1)" means a compound represented by formula (1), and may also mean at least one compound represented by formula (1).

[0037] [Component A and Component B] As described above, the problem of the present application can be solved by using a composition containing Component A as an epoxy compound and at least one of Component B below as a curing agent.

[0038] Component A: a compound having two or more oxiranyl groups and 2 to 5 aromatic rings, in which 1 to 3 hydrogen atoms of the aromatic rings have been replaced with groups derived from vinyl. Component B: A compound having two or more phenolic hydroxyl groups or two or more cyanate esters and having two to five aromatic rings, in which one to three hydrogen atoms of the aromatic rings have been replaced with groups derived from vinyl.

[0039] The vinyl-derived group is a group in which vinyl or vinyl H is replaced with a monovalent organic group. In this case, there is no limitation on the number of vinyl substitutions, but in order to improve heat resistance, it is preferable that the vinyl is unsubstituted or monosubstituted. There is also no limitation on the substitution position of the vinyl.

[0040] The number of vinyl-derived groups in the compound of component A or component B is 1 to 3, but in order to improve the liquid crystallinity of the composition, 1 to 2 is preferred, and 1 is most preferred.

[0041] In order to further improve the heat resistance of the epoxy resin cured product, it is preferable to use a composition containing both Component A and Component B of the present invention. On the other hand, in order to adjust the physical properties of the cured product, such as adjusting the linear expansion coefficient, it is also preferable to use a composition containing either Component A or Component B of the present invention. Furthermore, for the same purpose, other known epoxy resin compositions may be added to the composition of the present invention.

[0042] In order to improve the thermal conductivity after curing, it is preferable to arrange the molecular skeleton in a highly ordered manner in the epoxy resin cured product. Therefore, it is preferable to enhance the liquid crystallinity of the epoxy resin composition or during its curing. To enhance the liquid crystallinity, it is preferable that the structure of the compound of component A or component B has a structure in which aromatic rings are linked together.

[0043] It is also preferable to impart liquid crystallinity to the compounds of components A and B themselves in order to enhance the liquid crystallinity of the epoxy resin composition or its curing state. In this case, to impart liquid crystallinity to the compound, it is preferable that the core has a structure in which aromatic rings are linearly connected and flexible substituents such as alkyl are bonded to both ends of the core. The core of a compound having liquid crystallinity refers to a structure in which aromatic rings or alicyclic rings are connected by a bonding group with a relatively fixed conformation. Examples of such bonding groups include a single bond, ethylene, oxymethylene, a double bond, or a triple bond. The above-mentioned "straight line" does not need to be strictly linear and may be bent at an angle of about 45 degrees.

[0044] For the above-mentioned compounds having liquid crystallinity, the core preferably has two to five aromatic rings in order to expand the liquid crystal temperature range. To improve the compatibility between components or to reduce material costs, it is more preferable for the core to have two to four aromatic rings. Furthermore, to satisfy both the above-mentioned liquid crystallinity and compatibility characteristics, it is most preferable for the core to have three aromatic rings.

[0045] In order to impart high thermal conductivity and heat resistance to the cured epoxy resin, the component A of the present invention is preferably a compound represented by formula (A). TIFF0007725880000018.tif32139 In formula (A), R ep are independently a group having 3 to 12 carbon atoms, including oxiranyl. X is independently a single bond, alkylene having 1 to 12 carbon atoms, -CHO-, -CH=CH-, or -C≡C-. R 1 At least one of R is a group represented by formula (1), and the other R 1 are independently hydrogen, alkyl having 1 to 5 carbon atoms, or alkoxy having 1 to 5 carbon atoms, and n is an integer of 0 to 2. TIFF0007725880000019.tif2648 In formula (1), R 2 are independently hydrogen or alkyl having 1 to 12 carbon atoms, and * indicates the bonding position to the aromatic ring.

[0046] In the structure of formula (A), X is a single bond, -(CH2)2-, -(CH2)4-, -(CH2)6-, -(CH2)8-, or -(CH2) 10 -, -(CH2) 12 Preferably, it is - or -C≡C-, more preferably a single bond, -(CH2)2-, -(CH2)4- or -C≡C-, and most preferably a single bond. Preferred examples of such formula (A) include compounds represented by formulae (A-1) to (A-11).

[0047] TIFF0007725880000020.tif211113 TIFF0007725880000021.tif192139

[0048] In formulas (A-1) to (A-11), R ep is a group having 3 to 12 carbon atoms containing oxiranyl, and R 10 and R 11 are independently hydrogen or alkyl having 1 to 6 carbon atoms, and 10 and R 11 At least one of is hydrogen.

[0049] In the above formulas (A-1) to (A-11), R ep is preferably glycidyl, and R 10 and R 11 is preferably hydrogen or alkyl having 1 to 3 carbon atoms.

[0050] It is somewhat difficult to synthesize component B, which has a structure in which flexible substituents are bonded to both ends of the core. Such compounds are unlikely to exhibit liquid crystallinity. However, when the compound of component B of the present invention is mixed with another compound having an aromatic ring, it readily interacts with the compound. Therefore, when the compound of component A or other known epoxy compounds exhibit liquid crystallinity, the liquid crystallinity of the epoxy compound is not impaired. As a result, the composition of the present invention exhibits high liquid crystallinity.

[0051] In order to impart high thermal conductivity and heat resistance to the cured epoxy resin, the component B of the present invention is preferably a compound having a structure represented by formula (BI). TIFF0007725880000022.tif32135In formula (BI), X is independently a single bond, an alkylene having 1 to 12 carbon atoms, -CHO-, -CH=CH-, or -C≡C-. R 1 At least one of R is a group represented by formula (1), and the other R 1 are independently hydrogen, alkyl having 1 to 5 carbon atoms, or alkoxy having 1 to 5 carbon atoms, and n is an integer of 0 to 2. TIFF0007725880000023.tif2648 In formula (1), R 2 are independently hydrogen or alkyl having 1 to 12 carbon atoms, and * indicates the bonding position to the aromatic ring.

[0052] Alternatively, the component B of the present invention is preferably a compound having a structure represented by formula (B-II). TIFF0007725880000024.tif32145 formula (B-II), X is independently a single bond, alkylene having 1 to 12 carbon atoms, -CHO-, -CH=CH-, or -C≡C-; R 1 At least one of R is a group represented by formula (1), and the other R 1 are independently a group represented by hydrogen, alkyl having 1 to 5 carbon atoms, or alkoxy having 1 to 5 carbon atoms, R 3 are independently alkyl having 1 to 6 carbon atoms or phenyl, n is an integer from 0 to 2.

[0053] Furthermore, the component B of the present invention is preferably a compound having a structure represented by formula (B-III). TIFF0007725880000025.tif32141In formula (B-III), X is independently a single bond, an alkylene having 1 to 12 carbon atoms, -CHO-, -CH=CH-, or -C≡C-. R 1 At least one of R is a group represented by formula (1), and the other R 1 are independently hydrogen, alkyl having 1 to 5 carbon atoms, or alkoxy having 1 to 5 carbon atoms, and n is an integer of 0 to 2.

[0054] In the compounds represented by formula (BI), formula (B-II), and formula (B-III), X is preferably a single bond, -(CH2)2-, -(CH2)4-, -(CH2)6-, -(CH2)8-, or -(CH2) 10 -, -(CH2) 12 Preferably, it is - or -C≡C-, more preferably a single bond, -(CH2)2-, -(CH2)4- or -C≡C-, and most preferably a single bond. Preferred examples of such compounds (BI), (B-II) and (B-III) include compounds represented by the following formulas (B-1) to (B-13).

[0055] TIFF0007725880000026.tif250104 TIFF0007725880000027.tif229131

[0056] In formulas (B-1) to (B-13), R 12 are independently a hydroxyl group, a group in which the hydroxyl group is acylated, or a cyanato group; R 10 and R 11 are independently hydrogen or alkyl having 1 to 6 carbon atoms, and 10 and R 11 At least one of is hydrogen.

[0057] In the above formulas (B-1) to (B-13), R 10 and R 11 is preferably hydrogen or alkyl having 1 to 3 carbon atoms.

[0058] The desired properties can be obtained by using one or more of the compounds of component A or component B in the composition of the present invention. Furthermore, other known epoxy compounds or curing agents can be used in combination as long as they do not impair the liquid crystallinity of the composition. When these components are used in combination, there are no particular restrictions on the content of the compound of component A or component B. However, to achieve the effects of the present invention, the content of component A or component B is preferably 30% by weight to 100% by weight, and more preferably 50% by weight to 100% by weight, based on the total amount of the epoxy compound or curing agent, respectively.

[0059] [Epoxy compounds other than component A] As such an epoxy compound, liquid crystalline epoxy compounds represented by formulas (LC-1) to (LC-12) can be preferably used.

[0060] TIFF0007725880000028.tif201113 TIFF0007725880000029.tif74125

[0061] As the other epoxy compounds, non-liquid crystal epoxy compounds represented by formulas (o-1) to (o-15) are preferably used.

[0062] TIFF0007725880000030.tif170104

[0063] In formula (o-6), Z 10 is a single bond, -CH2-, -O-, -S-, -CH(CH3)-, -C(CH3)2-, -SO2-, or -C(CF3)2-.

[0064] TIFF0007725880000031.tif203109

[0065] In formula (o-7) and formula (o-8), Z 11 is >CH- or >CCH3-.

[0066] TIFF0007725880000032.tif140105

[0067] As the other epoxy compounds, resins made of compounds represented by formulae (o-20) to (o-24) are also preferably used.

[0068] TIFF0007725880000033.tif81170

[0069] In formula (o-20), Z 12 and Z 13 is independently a single bond, -CH2-, -O-, -S-, -CH(CH3)-, -C(CH3)2-, -SO2-, or -C(CF3)2-, and n21 is an integer of 1 or more and 5,000 or less. In formula (o-21) and formula (o-22), n21 is an integer of 1 or more and 5000 or less. n22 and n23 are independently 0 or 1, and when n21 is 2 or more, it may be different for each repeat. R 10 and R 11 is 1,4-phenylene, 4,4'-biphenylene, or cyclopentadienylene. In addition, hydrogen on the aromatic ring in these formulas (o-20) to (o-22) may be replaced with methyl.

[0070] TIFF0007725880000034.tif104109

[0071] In formula (o-23) and formula (o-24), Z 14 is independently a single bond, —CH(CH3)—, or —C(CH3)2—, and n21 is an integer of 1 or more and 5000 or less. In addition, hydrogen on the aromatic ring in formula (o-23) and formula (o-24) may be replaced by methyl.

[0072] The content of such known epoxy compounds in the composition of the present invention is not particularly limited, so long as the composition or its cured product exhibits the desired properties. That is, they can be used in an amount of 0.1 to 70% by weight based on the total weight of the epoxy compounds. In this case, to exhibit the effects of the present invention, the amount is preferably 0.1 to 60% by weight, more preferably 0.1 to 55% by weight, and most preferably 0.1 to 50% by weight.

[0073] [Other hardeners] The curing agent that can be used in combination with the composition of the present invention other than component B may be any known compound such as a phenol, phenol ester, cyanate ester, amine, carboxylic acid, carboxylic acid ester, acid anhydride, or thiol. In this case, it is preferable to use a phenol-based or cyanate ester-based curing agent in order to suppress curing of the composition at room temperature and improve storage stability.

[0074] The phenol-based curing agent is preferably at least one compound represented by the following formulas (p-1) to (p-6), since it does not significantly impair the liquid crystallinity of the composition and is easily available.

[0075] TIFF0007725880000035.tif42115 TIFF0007725880000036.tif56148 TIFF0007725880000037.tif10297

[0076] In formula (p-1), n31 is an integer of 2 or more and 4 or less; Ring B is benzene, naphthalene, anthracene, fluorene, or 9,9-diphenylfluorene, and in these rings B, at least one hydrogen may be replaced by alkyl having 1 to 3 carbon atoms or alkoxy having 1 to 3 carbon atoms. In formula (p-2), n32 and n33 independently represent integers of 1 to 3; Z 30 is a single bond, alkylene having 1 to 10 carbon atoms, -CH(CH3)-, -C(CH3)2-, -C(CF3)2-, -O-, -S-, or -SO2-, At least one hydrogen atom on the benzene ring may be replaced by alkyl having 1 to 3 carbon atoms. In formula (p-3) and formula (p-4), n34 is an integer of 1 or more and 5000 or less, n35 and n36 are independently 0 or 1, and when n34 is 2 or more, it may be different for each repetition. In formula (p-4), R 10 and R 11is 1,4-phenylene, 4,4'-biphenylene, cyclopentadienylene, In formula (p-5), n34 is an integer of 1 or more and 5000 or less, In formula (p-6), n34 is an integer of 1 or more and 5000 or less, Z 31 is independently a single bond, —CH(CH3)—, or —C(CH3)2—, and n34 is an integer of 1 or more and 5000 or less. In addition, hydrogen on the aromatic ring in formulas (p-3) to (p-6) may be replaced with methyl.

[0077] The amine-based curing agent is preferably at least one compound represented by the following formula (a-1) or (a-2), since it does not significantly impair the liquid crystallinity of the composition and is easily available. E 1 -Z-(LZ)nE 1 (a-1) L 1 -ZE (a-2)

[0078] In formulas (a-1) and (a-2), Z is independently a single bond, -O-, -NH-, -S-, -SO2-, -CO2-, or alkylene having 1 to 12 carbon atoms; In formula (a-1), E 1 are independently amino, alkylamino having 1 to 10 carbon atoms, hydroxyl group, or carboxy, and at least one E is amino or alkylamino having 1 to 10 carbon atoms; L is independently a single bond, cyclohexylene, phenylene, or naphthalene, and at least one hydrogen atom in these rings may be replaced by an alkyl group having 1 to 10 carbon atoms; n is an integer of 0 to 7. In formula (2-2), L 1 is hydrogen, cyclohexyl, phenyl, or naphthyl, and at least one hydrogen atom in these rings may be replaced by an alkyl group having 1 to 10 carbon atoms; E is amino or alkylamino having 1 to 10 carbon atoms.

[0079] Such compounds represented by formula (a-1) include aliphatic polyamines having 2 to 12 carbon atoms, such as ethylenediamine, trimethylenediamine, tetramethylenediamine, hexamethylenediamine, diethylenetriamine, triethylenetetramine, p-xylenediamine, and m-xylenediamine; p-phenylenediamine, N-methyl-p-phenylenediamine, N-ethyl-p-phenylenediamine, N-propyl-p-phenylenediamine, N-butyl-p-phenylenediamine, 2,5-diaminotoluene, m-phenylenediamine, N-methyl-m-phenylenediamine, N-ethyl-m-phenylenediamine, N-propyl-m-phenylenediamine, and N-butyl-m-phenylenediamine. Examples of suitable amines include aromatic polyamines such as 2,4-diaminotoluene, 2,6-diaminotoluene, o-phenylenediamine, 1,5-diaminonaphthalene, 4,4'-diaminodiphenylmethane, 4,4'-diaminodiphenylethane, 4,4'-diaminodiphenylpropane, 4,4'-diaminodiphenylether, 1,1-bis(4-aminophenyl)cyclohexane, 4,4'-diaminodiphenylsulfone, bis(4-aminophenyl)phenylmethane, m-tolidine, and o-tolidine; and alicyclic polyamines such as 1,4-cyclohexyldiamine, 1,3-cyclohexyldiamine, 1,2-cyclohexyldiamine, and 1,3-bis(aminomethyl)cyclohexane.

[0080] Among these, p-phenylenediamine, N-methyl-p-phenylenediamine, N-ethyl-p-phenylenediamine, N-propyl-p-phenylenediamine, N-butyl-p-phenylenediamine, 2,5-diaminotoluene, m-phenylenediamine, N-methyl-m-phenylenediamine, N-ethyl-m-phenylenediamine, N-propyl-m-phenylenediamine, N-butyl-m-phenylenediamine, 2,4-diaminotoluene, 2,6-diaminotoluene, 4,4'-diaminodiphenylmethane, 4,4'-diaminodiphenylethane, 4,4'-diaminodiphenylpropane, 4,4'-diaminodiphenyl ether, and 4,4'-diaminodiphenyl sulfone are particularly preferred because they have good compatibility when made into a composition and excellent storage stability.

[0081] Examples of the compound represented by formula (a-2) include aliphatic amines having 2 to 12 carbon atoms, such as n-propylamine, n-butylamine, n-pentylamine, n-hexylamine, n-octylamine, and n-dodecylamine; aromatic amines, such as aniline, o-toluidine, m-toluidine, p-toluidine, 2,3-dimethylaniline, 2,4-dimethylaniline, 2,6-dimethylaniline, 2,4,6-trimethylaniline, 2-ethylaniline, 1-naphthylamine, and 1-amino-2-methylnaphthalene; and alicyclic amines, such as cyclohexylamine and 2-methylcyclohexylamine. Among these, aniline, o-toluidine, m-toluidine, p-toluidine, 2,3-dimethylaniline, 2,4-dimethylaniline, 2,6-dimethylaniline, 2,4,6-trimethylaniline, and 2-ethylaniline are particularly preferred due to their good compatibility when formed into a composition and excellent storage stability.

[0082] Preferred carboxy-containing curing agents include phthalic acid, terephthalic acid, isophthalic acid, 1,4-naphthalenedicarboxylic acid, 2,3-naphthalenedicarboxylic acid, 2,6-naphthalenedicarboxylic acid, 2,2'-biphenyldicarboxylic acid, 4,4'-biphenyldicarboxylic acid, and benzophenone-4,4'-dicarboxylic acid.

[0083] The content of such known curing agents in the composition of the present invention is not particularly limited, so long as the composition or its cured product exhibits the desired properties. That is, they can be used in an amount of 0.1 to 70% by weight based on the total weight of the curing agent. In this case, to exhibit the effects of the present invention, the amount is preferably 0.1 to 60% by weight, more preferably 0.1 to 55% by weight, and most preferably 0.1 to 50% by weight.

[0084] In the composition of the present invention, there is no particular limitation on the ratio of the epoxy compound containing component A to the curing agent containing component B. In this case, to efficiently promote the reaction and improve heat resistance, it is preferable that the reactive groups of the epoxy compound and the curing agent are equivalent. For example, in the case of epoxy:phenol, the ratio is 1:1, and in the case of epoxy:amine, the ratio is 2:1.

[0085] [Curing accelerator] The composition of the present invention contains an epoxy compound (Component A) or a curing agent (Component B). To improve heat resistance, the composition of the present invention preferably further contains a curing accelerator. Examples of such curing accelerators include imidazole-based curing accelerators such as 2-ethyl-4-methyl-1H-imidazole, 2-phenyl-4-methyl-1H-imidazole, 1,2-dimethylimidazole, 2-undecylimidazole, 1-benzyl-2-methylimidazole, 1-cyanoethyl-2-undecylimidazole, and 1-cyanoethyl-2-ethyl-4-methylimidazole; phosphorus-based curing accelerators such as triphenylphosphine; amine-based curing accelerators such as 2,4,6-tris(dimethylaminomethyl)phenol, triethylenediamine, benzyldimethylamine, 2-(dimethylaminomethyl)phenol, 1,8-diazabicyclo[5.4.0]undec-7-ene, and 4-dimethylaminopyridine; and tetraalkylammonium salts. Among these curing accelerators, it is preferable to use imidazole-based curing accelerators because they have a curing temperature of 200° C. or less and have high curability.

[0086] The concentration of the curing accelerator in the composition of the present invention is preferably 0.1 wt % or more, more preferably 0.5 wt % or more, based on the weight of the polymerizable compound of the present invention, in order to efficiently promote the reaction and improve heat resistance, and is preferably 5 wt % or less, more preferably 3 wt % or less, based on the weight of the polymerizable compound of the present invention, in order to avoid deterioration of reliability due to sublimation of the curing accelerator.

[0087] [Inorganic filler] The composition for electronic devices of the present invention may contain an inorganic filler. The inorganic filler contained in the composition for electronic components may be a highly thermally conductive filler, such as a nitride, such as aluminum nitride, boron nitride, or silicon nitride. Diamond, graphite, silicon carbide, silicon, beryllia, magnesium oxide, aluminum oxide, zinc oxide, silicon oxide, copper oxide, titanium oxide, cerium oxide, yttrium oxide, tin oxide, holminium oxide, bismuth oxide, cobalt oxide, calcium oxide, aluminum nitride, boron nitride, silicon nitride, magnesium hydroxide, aluminum hydroxide, gold, silver, copper, platinum, iron, tin, lead, nickel, aluminum, magnesium, tungsten, molybdenum, or stainless steel. Boron nitride, aluminum nitride, or aluminum oxide is preferred. Boron nitride and aluminum nitride are preferred because they have very high thermal conductivity in the planar direction, a low dielectric constant, and high insulating properties. Hexagonal boron nitride (h-BN) and aluminum nitride are particularly preferred.

[0088] The shape of the inorganic filler may be spherical, amorphous, fibrous, rod-like, cylindrical, plate-like, tetrapod-like, etc. The type, shape, size, and amount of the inorganic filler may be appropriately selected depending on the purpose. For example, when a cured product (electronic component material) formed from the composition for electronic components requires insulation, the inorganic filler may be conductive as long as the desired insulation is maintained.

[0089] The average particle size of the inorganic filler is preferably, for example, 0.1 to 200 μm, and more preferably 1 to 100 μm. A particle size of 0.1 μm or more provides good thermal conductivity, while a particle size of 200 μm or less allows for a high filling rate. In this specification, the average particle size is based on particle size distribution measured using a laser diffraction / scattering method. That is, using analysis based on the Fraunhofer diffraction theory and the Mie scattering theory, a powder is divided into two particles at a certain particle size by a wet method, and the diameter at which the larger and smaller particles are equal in volume (based on volume) is defined as the median diameter.

[0090] When used in a heat dissipation member, for example, the amount of inorganic filler added is preferably 20 to 95% by weight, more preferably 50 to 95% by weight, based on the total amount of nonvolatile matter in the composition for electronic components. A content of 20% by weight or more is preferred because thermal conductivity increases. A content of 95% by weight or less is preferred because the heat dissipation member does not become brittle.

[0091] The inorganic filler may be used unmodified. Alternatively, its surface may be treated with a coupling agent. For example, boron nitride (h-BN) may be treated with a silane coupling agent. Since boron nitride particles have no reactive groups on their surface, the silane coupling agent bonds only to their periphery. Boron nitride treated with a coupling agent can form bonds with polymerizable compounds in compositions for electronic components, and this bond is thought to contribute to thermal conductivity. Therefore, coupling agents that react with oxiranyl, oxetanyl, or groups possessed by curing agents are preferred. For example, amine-based or oxiranyl- or oxetanyl-containing coupling agents are preferred. Specific examples include Sila-Ace S310, S320, S330, S360, S510, and S530 manufactured by JNC Corporation.

[0092] The inorganic filler may be treated with a coupling agent and then surface-modified with a compound having a polymerizable group (polymerizable compound) such as epoxy. For example, boron nitride (h-BN) treated with a silane coupling agent is surface-modified with a polymerizable compound. If the boron nitride surface-modified with a polymerizable compound can form a bond with the polymerizable compound or curing agent in the composition for electronic components, this bond is thought to contribute to thermal conductivity. For example, the polymerizable compound may be the polymerizable compound of the present invention represented by formula (1), or other polymerizable compounds.

[0093] [Other components] Other components that can be contained in the composition of the present invention are not particularly limited, and examples thereof include a polymerizable compound having a polymerizable group other than epoxy, a non-polymerizable compound, a polymerization initiator, and a solvent.

[0094] The polymerizable compound having a polymerizable group other than epoxy is not particularly limited as long as it does not deteriorate the properties of the electronic material of the present invention, and any known polymerizable compound can be used. Among them, compounds that undergo radical polymerization, such as acrylic compounds and styrene-based compounds, can be preferably used, and these compounds that have liquid crystallinity can be more preferably used. Examples of polymerization initiators include thermal polymerization initiators, photocationic polymerization initiators, and photoanionic polymerization initiators. Examples of thermal cationic polymerization initiators include sulfonium salts, boron trifluoride-amine complexes, dicyanazide, organic acid hydrazides, and toluenesulfonic acid esters. Known examples of photocationic initiators include sulfonium salts, iodonium salts, and nonionic initiators. Known examples of photoanionic initiators include oximes, carbamates, guanidinium carboxylates, and nifedipine.

[0095] When the composition of the present invention contains a compound capable of undergoing radical polymerization, such as an acrylic compound or a styrene-based compound, a radical polymerization initiator may be used.

[0096] The composition of the present invention may contain a solvent. Polymerization of the composition may be carried out in a solvent or without a solvent. Preferred solvents include, for example, 1,4-dioxane, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether acetate, propylene glycol monomethyl ether acetate, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monobutyl ether, 3-methoxy-3-methyl-1-butanol, dipropylene glycol methyl ether, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, ethylene glycol diethyl ether, and diethylene glycol diethyl ether. Examples of suitable solvents include propylene glycol dimethyl ether, N-methyl-2-pyrrolidone, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, methyl 3-methoxypropionate, ethyl 3-ethoxypropionate, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether propionate, diethyl carbonate, ethyl methyl carbonate, γ-butyrolactone, methyl lactate, ethyl lactate, butyl lactate, 2-ethylhexanol, 1-propanol, isobutyl alcohol, n-butanol, 2-pentanone, methyl isobutyl ketone, diisobutyl ketone, cyclopentanone, cyclohexanone, diacetone alcohol, and ethylene glycol. These solvents may be used alone or in combination.

[0097] Since the composition of the present invention has high polymerizability, a stabilizer may be added to facilitate handling. Known stabilizers can be used without limitation. Examples of such stabilizers include hydroquinone, 4-ethoxyphenol, and 3,5-di-t-butyl-4-hydroxytoluene (BHT).

[0098] Furthermore, additives (such as oxides) may be added to adjust the viscosity or color of the composition for electronic devices. Examples include titanium oxide for whitening, carbon black for blackening, and silica fine powder for viscosity adjustment. Furthermore, to further increase mechanical strength, inorganic fibers such as glass or carbon fiber, their cloths, or synthetic fibers such as polyvinyl formal, polyvinyl butyral, polyester, polyamide, or polyimide, or supramolecules may be added.

[0099] [Electronic component materials] The material for electronic components of the present invention is obtained by curing the composition for electronic components according to the second embodiment and molding the cured product according to the intended use. For example, the material for electronic components can be used as a heat dissipation member.

[0100] The material for electronic components is a polymer obtained by polymerizing (curing) the composition of the present invention. This polymer has high thermal conductivity and excellent chemical stability, heat resistance, hardness, and mechanical strength. The mechanical strength includes Young's modulus, tensile strength, tear strength, flexural strength, flexural modulus, and impact strength.

[0101] The composition of the present invention is a thermosetting resin. A thermosetting resin is cured by heating a raw material composition to polymerize the monomers contained in the composition and further three-dimensionally crosslink the monomers. The heating temperature is preferably within a temperature range in which the composition of the present invention exhibits a liquid crystal phase. Furthermore, the composition of the present invention may have an increased liquid crystal temperature range as the curing proceeds to a certain extent. In such cases, the composition may be cured within the increased liquid crystal temperature range.

[0102] The curing temperature may be constant or may be increased or decreased stepwise. In the latter case, the initial curing temperature is preferably a temperature at which the composition or its cured product exhibits a liquid crystal phase in order to improve the heat dissipation characteristics of the material. Furthermore, heating at a temperature higher than the initial curing temperature is preferred in order to improve heat resistance. When curing is performed stepwise at different temperatures, it is preferred to use multiple heating devices set at constant but different temperatures to shorten the production time of the cured product.

[0103] The thermosetting temperature for thermal polymerization is in the range of 20°C to 350°C, preferably 20°C to 250°C, and more preferably 50°C to 200°C. The curing time is in the range of 5 seconds to 10 hours, preferably 1 minute to 8 hours, and more preferably 5 minutes to 5 hours. After polymerization, slow cooling is preferred to suppress stress distortion, etc. Furthermore, reheating may be performed to relieve distortion, etc.

[0104] A crosslinking agent may be added to further crosslink the polymer. This allows a polymer (cured product) with excellent chemical resistance and heat resistance to be obtained. Any known crosslinking agent can be used without limitation, and examples thereof include trimethylolpropane tris(3-mercaptopropionate).

[0105] The material for electronic components of the present invention can be used in the form of a sheet, film, thin film, fiber, molded product, or the like. Films and thin films are preferred. Films and thin films can be obtained by polymerizing a composition for electronic components in a state where the composition is applied to a substrate or sandwiched between substrates. Alternatively, the composition can be obtained by applying a solvent-containing composition for electronic components to a substrate and then removing the solvent. Furthermore, films can be obtained by press molding of a polymer. In this specification, the thickness of a sheet is 1 mm or more, the thickness of a film is 5 μm or more, preferably 10 to 900 μm, and more preferably 20 to 800 μm, and the thickness of a thin film is less than 5 μm. The thickness may be appropriately changed depending on the application.

[0106] The material for electronic components of the present invention has excellent properties such as high thermal conductivity, chemical stability, heat resistance, hardness, and mechanical strength, and is therefore useful for heat sink plates, heat sink sheets, heat sink films, heat sink coatings, heat sink adhesives, heat sink molded products, etc.

[0107] Although the use of the material for electronic components formed from the polymerizable compound of the present invention as a heat dissipation material has been described above, the use of the material for electronic components is not limited to a heat dissipation material. For example, the material for electronic components may be used as a sealing material or an adhesive material.

[0108] [Method of manufacturing a composition for electronic components] The composition for electronic components refers to the heat dissipation material, which is the composition of the present invention, and may contain an inorganic filler to enhance thermal conductivity, regardless of whether the inorganic filler is subjected to a coupling treatment. As a production example of the composition for electronic components, a production method in which the inorganic filler is subjected to a coupling treatment will be described. A known method can be used for the coupling treatment.

[0109] As an example, first, inorganic filler particles and a coupling agent are added to a solvent. The mixture is stirred using a stirrer or similar device and then left to stand. After the solvent has dried, the mixture is heated under vacuum conditions using a vacuum dryer or similar device. The solvent is added to the inorganic filler particles, and the particles are pulverized using ultrasonic treatment. The solution is separated and purified using a centrifuge. After discarding the supernatant, the solvent is added and the same procedure is repeated several times. The purified inorganic filler particles are then dried using an oven.

[0110] Next, the coupling-treated inorganic filler particles and the polymerizable compound are mixed using an agate mortar or the like, and then kneaded using a two-axis roll or the like. After that, the mixture is separated and purified by ultrasonic treatment and centrifugation.

[0111] An amine-based curing agent is then added, and the mixture is mixed using an agate mortar or the like, followed by kneading using a two-screw roll or the like, to obtain a solvent-free composition for electronic components.

[0112] [Method of manufacturing materials for electronic components] As an example, a method for producing a film as a material for electronic components using a solvent-free composition for electronic components will be described.

[0113] The solvent-free composition for electronic devices is sandwiched between heating plates using a compression molding machine and molded by compression molding. The polymerizable compound is polymerized at a predetermined temperature and time to form a polymer. Post-curing may be performed for an appropriate time and temperature. The pressure during compression molding is 50 to 500 kgf / cm. 2 is preferable, and more preferably 70 to 250 kgf / cm 2 Generally, higher pressure is preferable during curing. However, it is best to apply an appropriate pressure, adjusting it depending on the fluidity of the mold and the desired physical properties (such as which direction of thermal conductivity is most important).

[0114] The composition for electronic components can be easily handled by partially curing it (semi-curing it). For example, the semi-cured composition can be formed into a sheet, cut into a desired shape, and placed between suitable components for bonding.

[0115] A method for producing a film as a material for electronic components using a solvent-containing composition for electronic components will be described.

[0116] The composition for electronic components is applied to a substrate, and the solvent is dried and removed to form a coating layer with a uniform thickness. Examples of the coating method include spin coating, roll coating, caten coating, flow coating, printing, microgravure coating, gravure coating, wire bar coating, slit coating, dip coating, spray coating, and meniscus coating.

[0117] The solvent can be removed by drying, for example, air drying at room temperature, drying on a hot plate, drying in a drying oven, blowing warm or hot air, etc. The conditions for solvent removal are not particularly limited, and drying may be carried out until the solvent is mostly removed and the coating layer loses its fluidity.

[0118] [Electronic Components] An example of an electronic component is an electronic device having a heat-generating portion. When the material for electronic components of the present invention is used as a heat dissipation member, the heat dissipation member is placed on the electronic device so as to contact the heat-generating portion. The heat dissipation member may be in the form of a heat dissipation plate, a heat dissipation sheet, a heat dissipation film, a heat dissipation adhesive, a heat dissipation molded product, or the like. In this way, the heat dissipation member dissipates heat generated in the electronic device, preventing heat-related breakdowns and extending the life of electronic devices incorporating the electronic device.

[0119] Semiconductor elements are an example of an electronic device. Heat dissipation materials have high thermal conductivity, as well as high heat resistance and insulation. Therefore, they are particularly effective for insulated gate bipolar transistors (IGBTs), which require a more efficient heat dissipation mechanism due to their high power consumption. IGBTs are a type of semiconductor element, a bipolar transistor with a MOSFET built into the gate, and are used for power control. Electronic devices equipped with IGBTs include the main conversion element of high-power inverters, uninterruptible power supplies, variable voltage and variable frequency control devices for AC motors, control devices for railway vehicles, electric transportation equipment such as hybrid cars and electric cars, and induction cookers.

[0120] [Method for synthesizing compounds represented by formula (A1), formula (B1), and formula (B2)] The compounds represented by formula (A1), formula (B1), and formula (B2) can be synthesized by combining known methods in organic synthetic chemistry. Methods for introducing desired polymerizable groups and ring structures into starting materials are described in, for example, Houben-Weyl, Methods of Organic Chemistry, Georg Thieme Verlag, Stuttgart; Organic Syntheses, John Wiley & Sons, Inc.; Organic Reactions, John Wiley & Sons, Inc.; Comprehensive Organic Synthesis, Pergamon Press; and New Experimental Chemistry Lectures (Maruzen). Reference may also be made to Japanese Patent Application Laid-Open No. 2006-265527. Some of these methods are also disclosed in the Examples. [Example]

[0121] The present invention will be described in detail below using examples. However, the present invention is not limited to the contents described in the examples. Unless otherwise specified, measurements were carried out at 23°C.

[0122] [Measuring the phase transition temperature of compounds and identifying liquid crystal phases] Measurements were performed using a polarizing microscope (Nikon) equipped with a hot stage (Mettler Toledo) and a differential scanning calorimeter (Perkin Elmer, Diamond DSC). Polarizing microscope measurements were performed under crossed Nicols. The heating rate for both measurements was 3°C / min. C indicates crystal, S indicates smectic phase, N indicates nematic phase, I indicates isotropic liquid, and () indicates monotropic liquid crystal phase.

[0123] [NMR measurement] NMR was measured using a VARIAN NMR SYSTEM manufactured by VARIAN. 1The magnetic field strength for H NMR measurements was 500 MHz, and the sample was dissolved in a deuterated solvent such as CDCl3. Measurements were performed at room temperature. The number of accumulations was 8. The internal standard was tetramethylsilane. In the NMR symbols, s means singlet, d means doublet, t means triplet, m means multiplet, and br means broad.

[0124] [Confirmation of liquid crystal properties of the composition] The composition was sandwiched between glass plates, melted, and then rapidly cooled to ensure uniform adhesion between the plates. The resulting sample was heated to 200°C at a heating rate of 5°C / min and then rapidly cooled to room temperature. The sample was observed under crossed Nicols using the polarizing microscope described above. The magnifications of the eyepiece and objective lens were 10x10. If light leakage due to scattering was observed in 50% or more of the observation area, the composition was determined to have liquid crystallinity. Alternatively, if the composition gave a vertically aligned cured product, a dark field was observed under the microscope. Therefore, light leakage caused by tilting the sample under crossed Nicols was visually confirmed.

[0125] [Evaluation of heat resistance by measuring the glass transition temperature (Tg)] Measurement was performed using a Rigaku Thermo Plus EVO2 DSC-8231 high-sensitivity DSC-type differential scanning calorimeter. The composition placed in an aluminum pan was heated to 150°C at a heating rate of 10°C / min and maintained at that temperature for 30 minutes. It was then cooled to 40°C at a heating rate of 10°C / min and heated again to 200°C at a heating rate of 10°C / min. The glass transition temperature was determined from the DSC curve obtained during the second heating process.

[0126] [Measurement of thermal conductivity] Samples consisting of resin only: NETZSCH LFA467 HyperFlash was used to measure the thermal diffusivity (α, m 2 The thermal diffusivity was measured in the in-plane direction and thickness direction of the sample. The specific heat (c, J / (Kg)) and density (ρ, g / m 3 ) and the thermal conductivity (W / (Km)) was calculated according to the following formula. κ=αxcxρ The specific heat was measured using a DSC-type high-sensitivity differential scanning calorimeter Thermo Plus EVO2 DSC-8231 manufactured by Rigaku Corp. The specific gravity was measured using a specific gravity scale type hydrometer DME-220 manufactured by Shinko Denshi Co., Ltd. Filler-containing samples: The thermal diffusivity in the thickness direction of the samples was measured using an ai-Phase Mobile 1u thermal diffusivity measuring device manufactured by ai-Phase Corporation. The specific heat and density of the samples were also measured in the same manner as above. From these values, the thermal conductivity was calculated in the same manner as above.

[0127] [Epoxy compounds and curing agents] As the epoxy compound represented by formula (A), the compounds represented by the following formulas (A-1-1), (A-7-1), (A-7-2) and (A-10-1) were used in the examples. These compounds were synthesized as described below. In addition, an epoxy compound represented by YX4000H (manufactured by Mitsubishi Chemical Corporation) was used as an epoxy compound other than component A. Furthermore, epoxy compounds represented by the following formula (LC-6) and compound (LC-10) were also used. These compounds were synthesized according to Japanese Patent Application No. 2021-083058. The curing agent represented by formula (BI) was the compound represented by the following formula (B-1-1), formula (B-1-2), formula (B-1-3), formula (B-1-4), formula (B-9-1), formula (B-9-2), and formula (B-12-1). In addition, the curing agent other than component B was DHTP-M (manufactured by Honshu Chemical Industry Co., Ltd.), a curing agent described in JP 2015-209529 A.

[0128] TIFF0007725880000038.tif24116 TIFF0007725880000039.tif24134 TIFF0007725880000040.tif28133 TIFF0007725880000041.tif20157 TIFF0007725880000042.tif20104 TIFF0007725880000043.tif28116 TIFF0007725880000044.tif2596 TIFF0007725880000045.tif20102 TIFF0007725880000046.tif21111 TIFF0007725880000047.tif28111 TIFF0007725880000048.tif21135 TIFF0007725880000049.tif28138 TIFF0007725880000050.tif27141 TIFF0007725880000051.tif22117

[0129] [Commercially available hardeners] As amine-based curing agents, 1,3-phenylenediamine (PDA) and 3,5-dimethylaniline (DMA) were manufactured by Tokyo Chemical Industry Co., Ltd. and used as they were without purification. As a phenol-based curing agent, 4,4'-dihydroxybiphenyl (BPOH) was used as they were without purification.

[0130] [Curing accelerator] Curesol 2PZ-PW (manufactured by Shikoku Chemicals Corporation), an imidazole-based curing accelerator, was used as is without purification.

[0131] [Reference example 1] Synthesis of the compound represented by formula (B-9-1) TIFF0007725880000052.tif24169In the above formula, THPO is tetrahydro-2H-pyran-2-yloxy, and PPTS represents pyridinium p-toluenesulfonate.

[0132] A mixture of 1.00 g (3.81 mmol) of 2,5-dibromostyrene, 1.86 g (8.38 mmol) of 4-(Tetrahydro-2H-pyran-2-yloxy)phenylboronic acid, 0.220 g (0.190 mmol) of tetrakistriphenylphosphine palladium(0), and 1.62 g (15.3 mmol) of Na2CO3 was refluxed in 20 ml of dimethoxyethane under a nitrogen atmosphere for 3 hours. 2,5-Dibromostyrene was synthesized according to the procedure described in Journal of the American Chemical Society, vol. 134, p. 16131 (2012). After the reaction was complete, the reaction solution was cooled, and 60 ml each of purified water and toluene were added. The organic layer was separated, washed twice with the same amount of purified water, and dried over anhydrous MgSO4. After filtration and distillation of the solvent under reduced pressure, the resulting product was purified by column chromatography (silica gel, toluene / ethyl acetate=10 / 1) to obtain 1.26 g (72% yield) of compound (B-9-1-a).

[0133] A mixture of 1.57 g (3.43 mmol) of compound (B-9-1-a) and 346 mg (1.38 mmol) of pyridinium p-toluenesulfonate was stirred at room temperature for 2 days in a tetrahydrofuran (THF) / methanol (10 ml / 10 ml) mixed solvent. Ethyl acetate (30 ml) and purified water (30 ml) were added, and the mixture was separated. The organic layer was washed with purified water (20 ml) and then dried over anhydrous MgSO4. After filtration and distillation under reduced pressure, the resulting product was purified by recrystallization (ethanol / toluene) to obtain compound (B-9-1). Yield: 833 mg (84%).

[0134] Melting point (℃): 191-194. 1H-NMR(ppm,CDCl3);7.77(d,1H,J=2.50Hz),7.56-7.54(m,2H),7.49(dd,1H,J=8.00,2.50Hz),7.32(d,1H,J=8.00Hz),7.28-7. 25(m,2H),6.95-6.88(m,4H),6.80-6.75(m,1H),5.76(dd,1H,J=17.50,1.50Hz),5.23(dd,1H,J=11.0,1.00Hz),4.82(brs,2H)

[0135] [Example 1] Synthesis of the compound represented by formula (A-7-1) TIFF0007725880000053.tif1967 A mixture of 1.00 g (3.47 mmol) of the compound represented by formula (B-9-1), 4.73 g (34.5 mmol) of epibromohydrin, and 1.92 g (13.9 mmol) of K2CO3 was refluxed in 10 ml of methyl ethyl ketone for 10 hours. After cooling, toluene (30 ml) and purified water (30 ml) were added to the reaction mixture, and the mixture was separated. The organic layer was washed with purified water (20 ml) and then dried over anhydrous MgSO4. After filtration and evaporation of the solvent under reduced pressure, the resulting product was purified by column chromatography (toluene:ethyl acetate = 10:1) to obtain compound (A-7-1). Yield: 1.03 g (74%). Phase transition point (℃): C·130.6·I 1 H-NMR(ppm,CDCl3);7.79(d,1H,J=2.00Hz),7.59-7.57(m,2H),7.49(dd,1H,J =8.00,2.00Hz),7.33-7.29(m,3H),7.03-7.95(m,4H),6.78-6.72(m,1H),5.7 5(dd,1H,J=17.50,1.50Hz),5.22(dd,1H,J=10.5,1.00Hz),4.29-4.25(m,2H) ,4.03-3.99(m,2H),3.40-3.38(m,2H),2.94-2.91(m,2H),2.79-2.77(m,2H).

[0136] [Example 2] Synthesis of compound represented by formula (B-9-2) TIFF0007725880000054.tif25169In the above formula, THPO and PPTS have the same meanings as above.

[0137] The compound represented by formula (B-9-2-a) was synthesized in the same manner as in Example 1, except that 1,4-dibromo-2-isopropenylbenzene was used instead of 2,5-dibromostyrene. The raw material, 1,4-dibromo-2-isopropenylbenzene, was synthesized according to DE2431144. The resulting product was purified by column chromatography (silica gel, toluene) to obtain compound (B-9-2-a). The yield was 67%.

[0138] Compound (B-9-2-a) was used to remove THP in the same manner as in Reference Example 1. The resulting product was purified by recrystallization (ethyl acetate / heptane) to obtain compound (B-9-2). Yield: 90%.

[0139] Melting point (℃): 140.5 1 H-NMR(ppm, CDCl3);7.55-7.52(m,2H),7.50-7.48(m,1H),7.60(d,1H,J=2.00Hz),7.36-7.31(m,3H),6.93-6.90(m ,2H),6.87-6.84(m,2H),5.11(dd,1H,J=1.50,1.50Hz),5.07(brs,1H),4.84(brs,1H),4.80(brs,1H),1.70(s,3H).

[0140] [Example 3] Synthesis of compound represented by formula (A-7-2) The compound represented by formula (B-9-2) was synthesized in the same manner as in Example 1. The resulting product was purified by column chromatography (toluene: ethyl acetate = 40:1) to obtain compound (A-7-2). Yield: 85%.

[0141] Phase transition point (℃): C·131.9·I 1H-NMR(ppm, CDCl3);7.59-7.56(m,2H),7.51-7.49(m,2H),7.47(d,1H,J=2.00Hz ),7.40-7.38(m,2H),7.33(d,2H,J=8.00Hz),7.02-6.99(m,2H),6.95-6.92(m,2H ),5.11(dd,1H,J=1.50,1.50Hz),5.07(brs,1H),4.29-4.25(m,2H),4.04-3.99(m ,2H),3.41-3.38(m,2H),2.94(t,2H,J=4.50Hz),2.80-2.78(m,2H),1.70(s,3H).

[0142] [Example 4] Synthesis of compound represented by formula (B-12-1) TIFF0007725880000056.tif67168 In the above formula, Tf is trifluoromethanesulfonyl, and THP and PPTS have the same meanings as above.

[0143] To a solution of 2.00 g (9.34 mmol) of 3-formyl-4,4'-dihydroxybiphenyl and 6.6 mL of pyridine in 20 mL of methylene chloride, 3.4 mL (20.7 mmol) of trifluoromethanesulfonic anhydride was added at room temperature or below. The reaction mixture was stirred overnight, poured into 50 mL of purified water, and extracted with 50 mL of toluene. The organic layer was washed with dilute hydrochloric acid, purified water, and aqueous sodium bicarbonate (50 mL each) and then dried over anhydrous magnesium sulfate. The organic layer was filtered, the solvent was removed under reduced pressure, and the resulting product was purified by column chromatography (toluene) to obtain compound (B-12-1-a). Yield: 3.66 g (82%). In the above reaction, 3-formyl-4,4'-dihydroxybiphenyl was synthesized according to the method described in Journal of Medicinal Chemistry, vol. 52, p. 858 (2009).

[0144] 2.00 g (4.18 mmol) of compound (B-12-1-a) was reacted with 4-(Tetrahydro-2H-pyran-2-yloxy)phenylboronic Acid in the same manner as in Reference Example 1. The resulting product was purified by column chromatography (silica gel, toluene) to obtain compound (B-12-1-b). Yield: 1.45 g (65%).

[0145] A solution of 294 mg (2.62 mmol) of t-BuOK in 10 ml of THF was added to a solution of 868 mg (2.43 mmol) of methyltriphenylphosphonium bromide in 10 ml of THF at temperatures below 0°C. After stirring at 0°C for 30 minutes, the mixture was cooled to -20°C, and 1.00 g (1.87 mmol) of compound (B-12-1-b) was added. After stirring at room temperature for 2 hours, the mixture was poured into 50 ml of purified water and extracted with 50 ml of toluene. The organic layer was washed with 50 ml of purified water and then dried over anhydrous magnesium sulfate. The organic layer was filtered, the solvent was evaporated under reduced pressure, and the resulting product was purified by column chromatography (toluene) to obtain compound (B-12-1-c). Yield: 857 mg (86%).

[0146] Using 850 mg (1.60 mmol) of compound (B-12-1-c), compound (B-12-1) was synthesized in the same manner as in Reference Example 1. The product was purified by recrystallization (ethanol / toluene) to obtain compound (B-12-1). Yield: 512 mg (88%).

[0147] Melting point: 250°C or higher 1 H-NMR(ppm,CDCl3);7.87(d,1H,J=1.50Hz),7.73-7.70(m,2H),7.66-7.62(m,2H),7.58(dd,1H,J=7.50,2.00Hz),7.57-7.54(m,2H),7.37(d,1H, J=8.00Hz),7.30-7.27(m,2H),6.95-6.89(m,4H),6.79(dd,1H,J=17.0,11.0Hz),5.79(d,1H,J=17.0Hz),5.26(d,1H,J=11.5Hz),4.80(brs,2H).

[0148] [Example 5] Synthesis of compound represented by formula (A-10-1) TIFF0007725880000057.tif2164 It was synthesized from the compound represented by formula (B-12-1) in the same manner as in Example 1. Yield: 78%.

[0149] Phase transition temperature (℃): C 169.2 S > 300 I 1 H-NMR(ppm,CDCl3);7.87(d,1H,J=1.50Hz),7.73-7.70(m,2H),7.66-7.64(m,2H),7 .61-7.57(m,3H),7.37(d,1H,J=8.00Hz),7.34-7.32(m,2H),7.05-6.98(m,4H),6.79 (dd,1H,J=17.0,11.0Hz),5.79(d,1H,J=17.0Hz),5.25(d,1H,J=11.0Hz),4.31-4.27 (m,2H),4.05-4.01(m,2H),3.43-3.38(m,2H),2.96-2.93(m,2H),2.81-2.79(m,2H).

[0150] [Example 6] Synthesis of compound represented by formula (B-1-1) A mixture of 2.00 g (9.34 mmol) of 3-formyl-4,4'-dihydroxybiphenyl, 4.7 g (56 mmol) of 3,4-dihydro-2H-pyran, and 0.47 g (1.9 mmol) of PPTS was stirred overnight at room temperature in 20 mL of CHCl. 30 mL of saturated aqueous sodium bicarbonate was added to the reaction mixture, and the organic layer was separated. The organic layer was dried over anhydrous magnesium sulfate and then filtered. The solvent was removed under reduced pressure, and the resulting product was purified by column chromatography (toluene:ethyl acetate = 10:1) to obtain compound (B-1-1-a). Yield: 244 mg (7.9%).

[0151] Compound (B-1-1-a) was converted to compound (B-1-1-b) in the same manner as in Example 5. The crude product was purified by column chromatography (heptane:toluene=1:1→toluene). Yield: 86%.

[0152] Compound (B-1-1-b) was converted to compound (B-1-1) in the same manner as in Example 5. The crude product was purified by column chromatography (toluene:ethyl acetate=2:1). Yield: 100%.

[0153] Melting point (℃): 138.0-145.7. 1 H-NMR(ppm,CDCl3);7.54(d,1H,J=2.50Hz),7.44-7.41(AA'BB',2H),7.31(dd,1H,J=8.00,2.50Hz),6.97(dd,1H,J=17.50,10.50 Hz),6.91-6.87(AA'BB',2H),6.85(d,1H,J=8.50Hz),5.80(d,1H,J=18.00Hz),5.41(d,1H,J=11.00Hz),4.99(s,1H),4.76(s,1H).

[0154] [Example 7] Synthesis of the compound represented by formula (A-1-1) A mixture of 320 mg (1.51 mmol) of the compound represented by formula (B-1-1), 4.18 g (30.2 mmol) of epibromohydrin, and 1.25 g (9.05 mmol) of KCO was refluxed in 10 ml of DMF for 2 hours. After cooling, ethyl acetate (40 ml) and purified water (40 ml) were added to the reaction mixture, and the mixture was separated. The organic layer was washed with saturated brine (40 ml) and then dried over anhydrous MgSO. After filtration and evaporation of the solvent under reduced pressure, the resulting product was purified by column chromatography (toluene:ethyl acetate = 9:1) to obtain compound (A-1-1). Yield: 440 mg (90%). Melting point (℃): 60.0-77.1. 1H-NMR(ppm,CDCl3);7.65(d,1H,J=2.00Hz),7.50-7.47(m,2H),7.39(dd,1H,J=8.5 0,2.50Hz),7.11(dd,1H,J=18.0,11.0Hz),7.00-6.97(m,2H),6.92(d,1H,J=8.50Hz ),5.82(dd,1H,J=17.50,1.50Hz),5.32(dd,1H,J=11.0,1.50Hz),4.30-4.25(m,2H ),4.05-3.99(m,2H),3.42-3.37(m,2H),2.93(t,2H,J=4.50Hz),2.80-2.78(m,2H).

[0155] [Example 8] Synthesis of compound represented by formula (B-1-2) TIFF0007725880000060.tif1978 1.00 g (4.71 mmol) of compound (B-1-1) and 0.96 g (12.1 mmol) of pyridine were dissolved in 20 mL of CHCl solvent, and 1.16 g (11.4 mmol) of acetic anhydride was added at room temperature. The reaction mixture was stirred overnight. 20 mL of purified water was added to the reaction mixture, and the organic layer was separated. The organic layer was washed twice with 10 mL of purified water and then dried over anhydrous magnesium sulfate. After filtration, the solvent was removed under reduced pressure. The resulting product was purified by column chromatography (toluene:ethyl acetate = 10:1) to obtain compound (B-1-2). Yield: 1.21 g (87%).

[0156] Melting point (℃): 95.0-98.1. 1 H-NMR(ppm,CDCl3);7.72(d,1H,J=2.00Hz),7.60-7.56(AA'BB',2H),7.45(dd,1H,J=9.00,2.50Hz),7.18-7.15( AA'BB',2H),7.12(d,1H,J=8.00Hz),6.79(dd,1H,J=17.5,11.0Hz),5.82(d,1H,J=18.0Hz),5.38(d,1H,J=10Hz) 2.36(s,3H),2.34(s,3H).

[0157] [Example 9] Synthesis of compound represented by formula (B-1-3) TIFF0007725880000061.tif3075 To a solution of 3.00 g (14.1 mmol) of compound (B-1-1) and 3.5 ml (43.4 mmol) of triethylamine in 30 ml of CHCl, a solution of 2.7 ml (30.9 mmol) of propionic acid chloride in 10 ml of CHCl was added at 10°C or below. The reaction mixture was stirred at room temperature for 7 hours, after which 70 ml of toluene and 50 ml of purified water were added. The organic layer was separated and washed three times with purified water. After drying over anhydrous magnesium sulfate, it was filtered and the solvent was removed under reduced pressure. The resulting product was purified by column chromatography (toluene → toluene:ethyl acetate = 10:1) to obtain compound (B-1-3). Yield: 4.26 g (93%). Compound (B-1-3) was a liquid at room temperature.

[0158] 1 H-NMR(ppm,CDCl3);7.72(d,1H,J=2.50Hz),7.58-7.55(AA'BB',2H),7.46(dd,1H,J=9.00,2.50Hz),7.17-7.15(AA'BB',2H),7.11(d ,1H,J=9.00Hz),6.78(dd,1H,J=17.0,10.5Hz),5.81(d,1H,J=17.5Hz),5.37(d,1H,J=11.5Hz),2.68-2.60(m,4H),1.33-1.27(m,6H).

[0159] [Example 10] Synthesis of compound represented by formula (B-1-4) TIFF0007725880000062.tif2069 To a solution of 526 mg (4.96 mmol) of cyanogen bromide in 3 mL of diethyl ether, a solution of 500 mg (2.36 mmol) of compound (B-1-1) and 0.7 mL of triethylamine in diethyl ether was added over 15 minutes at -30°C. After stirring at room temperature for 1.5 hours, ethyl acetate (40 mL) and purified water (40 mL) were added to the reaction mixture, and the organic layer was separated. The organic layer was washed once with saturated brine (40 mL) and then dried over anhydrous magnesium sulfate. After filtration, the solvent was removed under reduced pressure, and the resulting product was purified by recrystallization (toluene:ethanol = 4:1) to obtain compound (B-1-4). Yield: 300 mg (49%).

[0160] Melting point (℃): 157 (decomposition) 1 H-NMR(ppm, CDCl3);7.72(d,1H,J=2.50Hz),7.66-7.62(AA'BB',2H),7.57(d,1H,J=8.50Hz),7.52(dd,1H,J=8. 5,2.5Hz)7.43-7.40(AA'BB',2H),6.91(dd,1H,J=17.5,11.0Hz),5.91(d,1H,J=18.0Hz),5.54(d,1H,J=11Hz).

[0161] [Example 11] Preparation of compositions and measurement of glass transition temperature (Tg) 29.30 mg (0.1016 mmol) of the compound represented by formula (B-9-1), 36.09 mg (0.1018 mmol) of YX4000H as an epoxy compound, and 0.89 mg of 2PZ-PW as a curing accelerator were mixed, and THF (1 ml) was added to completely dissolve the mixture. The solvent was removed under vacuum to obtain composition 11. 26.7 mg of this composition was weighed, and the glass transition temperature was measured, which was >200 °C.

[0162] [Comparative Example 1] Except for changing the compound represented by formula (B-9-1) to DHTP-M, composition ref1 was obtained in the same manner as in Example 11. 25.4 mg of this composition was weighed, and the glass transition temperature was measured, which was 115°C.

[0163] [Examples 12 to 17 and Comparative Example 2] Compositions 12 to 17 and ref2 shown in Table 1 were prepared in the same manner as in Example 11, and Tg was measured. Example 11 and Comparative Example 1 are listed again in Table 1. The values in parentheses for Example 16 in the table are the molar ratios of each curing agent relative to the total curing agent. Table 1. Glass transition temperature (Tg) of the composition TIFF0007725880000063.tif57114

[0164] Comparison of the above examples with the comparative examples reveals that the composition according to the present technology has a high glass transition point and high heat resistance.

[0165] [Example 18] 0.500 g (1.249 mmol) of the compound represented by formula (A-7-1) synthesized in Example 2 and 0.0675 g (0.625 mmol) of PDA were placed in a sample bottle, and tetrahydrofuran (5 mml) was added to dissolve the solids. This solution was vacuum dried at room temperature for 2 hours to obtain a composition of the present invention (Composition 18) as a viscous liquid. When this composition was observed under a polarizing microscope on a hot plate, light leakage due to scattering was observed over almost the entire observation area. The glass transition temperature of this sample was also measured and found to be above 200°C.

[0166] [Example 19] 0.500 g (1.249 mmol) of the compound represented by formula (A-7-1) synthesized in Example 2, 0.0545 g (0.504 mmol) of PDA, and 0.0303 g (0.250 mmol) of DMA were placed in a sample bottle, and tetrahydrofuran (5 mml) was added to dissolve the solids. This solution was vacuum dried at room temperature for 2 hours to obtain a composition of the present invention (Composition 19) as a viscous liquid. When this composition was observed under a polarizing microscope on a hot plate, light leakage due to scattering was observed over almost the entire observation area. The glass transition temperature of this sample was also measured and found to be above 200°C.

[0167] [Example 20] The liquid crystallinity and alignment of Compositions 15 to 17 prepared in Examples 15 to 17 were confirmed. As a result, it was confirmed that the compositions had liquid crystallinity and were cured in a vertically aligned state for all cured products.

[0168] Comparative Example 3 The liquid crystallinity of composition ref. 2 prepared in Comparative Example 2 was confirmed. Microscopic observation revealed that the cured product contained a mixture of regions that were considered to be crystalline and regions that were considered to be amorphous. When this cured product sample was measured at various temperatures, it was confirmed that in the region that was considered to be amorphous, there were parts that exhibited liquid crystallinity at temperatures of 110°C or higher. This suggests that in composition ref. 2, the curing agent was not compatible with the epoxy compound, and therefore curing was insufficient.

[0169] A comparison between Example 20 and Comparative Example 3 reveals that the composition of the present invention has high compatibility.

[0170] [Example 21] Measurement of thermal conductivity of cured material prepared from composition 11 Composition 11 was placed in a 2.4 cm diameter aluminum container and held on a hot plate heated to 150°C for 120 minutes, after which a circular piece 1.5 mm thick was removed. The thermal conductivity of this cured product (Cured Product 11) was 0.73 W / m K and 0.30 W / m K in the in-plane and thickness directions of the sample, respectively.

[0171] [Example 22] to [Example 29] The thermal conductivity of compositions 12 to 19 in Table 2 was measured using the same method as in Example 21. The values in parentheses for Examples 26 and 28 in the table indicate the molar ratio of each curing agent to the total curing agent. Example 21 is also shown here again.

[0172] Table 2. Liquid crystallinity and thermal conductivity of the composition TIFF0007725880000064.tif73145

[0173] [Example 30] Preparation of filler-containing samples 0.100 g of Composition 11 and 0.9000 g of boron nitride particles (PolarTherm PTX-25, manufactured by Momentive Performance Materials Japan, Inc.) were weighed out and mixed thoroughly, sandwiched between stainless steel plates, and held for 45 minutes at 20 MPa in a compression molding machine (IMC-19EC, manufactured by Imoto Machinery Co., Ltd.) heated to 150°C. A square piece with a thickness of 768 μm was then extracted as a heat dissipation component. The thermal conductivity of this sample (filler-containing Sample 11) was 8.9 W / m K.

[0174] [Example 31] to [Example 38] Filled compositions 12 to 19 were molded in the same manner as in Example 30 above, except that compositions 12 to 19 were used instead of composition 11. The thermal conductivity of these samples was measured, and the results are shown in Table 3. Example 30 is also listed in the table.

[0175] Table 3. Thermal conductivity of filled samples TIFF0007725880000065.tif62142

[0176] [Example 39] and [Example 40] 0.1 g of Composition 15 or Composition 16 and 0.90 g of aluminum oxide particles (DAW-10 manufactured by Denka) were weighed out and mixed well, and the mixture was subjected to the same procedure as in Example 30 to prepare Filler-containing Sample 15. AO and 16 AO The thermal conductivity was measured and the results are shown in Table 4.

[0177] Table 4. Thermal conductivity of filled samples2 TIFF0007725880000066.tif26140 As noted above, the compositions of the present invention are found to provide high thermal conductivity. [Industrial Applicability]

[0178] The technology of the present invention can be suitably used for packaging materials for semiconductor devices, and can also be used as an alternative to other epoxy resins, such as adhesives.

Claims

1. In a composition containing an epoxy compound and a curing agent, A composition containing at least one of component A as an epoxy compound and component B as a curing agent. Component A: A compound having two oxiranyl groups and two to four aromatic rings, in which one to three hydrogen atoms of the aromatic rings are replaced by groups derived from vinyl, and which is represented by formula (A). In formula (A), R ｅｐ are independently a group having 3 to 12 carbon atoms including oxiranyl, X is independently a single bond, —CH ２ -O-, -CH=CH-, or -C≡C-; R １ At least one of R is a group represented by formula (1), and the other R １ are independently hydrogen, alkyl having 1 to 5 carbon atoms, or alkoxy having 1 to 5 carbon atoms; n is an integer from 0 to 2. In formula (1), R ２ are independently hydrogen or alkyl having 1 to 12 carbon atoms, and * indicates the bonding position to the aromatic ring. Component B: A compound having two phenolic hydroxyl groups, groups in which the hydroxyl groups are acylated, or two cyanate esters, and having two to four aromatic rings, in which one to three hydrogen atoms on the aromatic rings have been replaced with groups derived from vinyl, represented by formula (BI), formula (B-II), or formula (B-III). In formula (BI), X is independently a single bond, —CH ２ -O-, -CH=CH-, or -C≡C-; R １ At least one of R is a group represented by formula (1) (excluding 1-propenyl), and the other R １ are independently hydrogen, alkyl having 1 to 5 carbon atoms, or alkoxy having 1 to 5 carbon atoms; n is an integer from 0 to 2. In formula (1), R ２ are independently hydrogen or alkyl having 1 to 12 carbon atoms, and * indicates the bonding position to the aromatic ring. In formula (B-II), X is independently a single bond, —CH ２ -O-, -CH=CH-, or -C≡C-; R １ At least one of R is a group represented by formula (1), and the other R １ are independently a group represented by hydrogen, alkyl having 1 to 5 carbon atoms, or alkoxy having 1 to 5 carbon atoms, R ３ are independently alkyl having 1 to 6 carbon atoms or phenyl, n is an integer from 0 to 2. In formula (1), R ２ are independently hydrogen or alkyl having 1 to 12 carbon atoms, and * indicates the bonding position to the aromatic ring. In formula (B-III), X is independently a single bond, —CH ２ -O-, -CH=CH-, or -C≡C-; R １ At least one of R is a group represented by formula (1), and the other R １ are independently a group represented by hydrogen, alkyl having 1 to 5 carbon atoms, or alkoxy having 1 to 5 carbon atoms, n is an integer from 0 to 2. In formula (1), R ２ are independently hydrogen or alkyl having 1 to 12 carbon atoms, and * indicates the bonding position to the aromatic ring.

2. The composition according to claim 1, wherein in the compound represented by formula (A), X is a single bond or -C≡C-.

3. The composition according to claim 1, wherein in the compound represented by formula (BI), X is a single bond or —C≡C—.

4. The composition according to claim 1, wherein in the compound represented by formula (B-II), X is a single bond or —C≡C—.

5. The composition according to claim 1, wherein in the compound represented by formula (B-III), X is a single bond or —C≡C—.

6. The composition of claim 1 further comprising a cure accelerator.

7. The composition of claim 6 further comprising an inorganic filler.

8. The composition of claim 7, wherein the inorganic filler is aluminum oxide, boron nitride, or aluminum nitride.

9. A cured product obtained by curing the composition according to any one of claims 1 to 8.

10. A material for electronic parts, which uses the cured product of claim 9.

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