Unsaturated group-containing phosphate ester, thermosetting resin composition containing the same, and resin material

Abstract

The present invention addresses the problem of providing a highly heat-resistant thermosetting resin composition able to be used in a high frequency printed circuit board. Provided is a phosphoric acid ester compound having an ethylenically unsaturated bond. This compound can be added as a modifier to a thermosetting resin such as an ethylenically unsaturated bond-containing poly(phenylene ether) resin. Also provided is a thermosetting resin composition that contains this modifier and a thermosetting resin. This thermosetting resin composition has the advantage of exhibiting high heat resistance. Furthermore, it is possible to achieve excellent dielectric properties and high heat resistance, which are required of printed circuit boards for next generation communication standards.

Description

Technical Field

[0001] The present invention relates to a phosphate ester having a copolymerizable unsaturated bond. In particular, the present invention relates to an unsaturated group-containing phosphate ester useful as a modifier for printed circuit boards and the like. The present invention also relates to a resin composition that can be used for printed circuit boards corresponding to next-generation communication standards, such as 5G or 6G communication standards.

Background Art

[0002] In printed circuit boards, it has been widely practiced to use epoxy resins. Further, it has been conventionally practiced to add a phosphate ester as a flame retardant to epoxy resins.

[0003] As a flame retardant added to epoxy resins, for example, Japanese Patent Application Laid-Open No. 5-1079 (Patent Document 1) discloses resorcinol bis(2,6-xylyl) phosphate.

[0004] Further, Japanese Patent Application Laid-Open No. 2003-221415 (Patent Document 2) discloses di(substituted phenyl)-2-(meth)acryloyloxyethyl phosphate as an unsaturated group-containing phosphate ester having excellent hydrolysis resistance. This document discloses that the problem of hydrolysis resistance during emulsion polymerization or suspension polymerization is solved by this unsaturated group-containing phosphate ester.

[0005] However, the resin compositions using these additives have the drawback of having lower heat resistance compared to the resin compositions without using such additives. This problem of heat resistance has not been solved in Patent Documents 1 and 2 mentioned above. In recent years, information technology has developed by leaps and bounds, and printed circuit boards compatible with communication standards such as 5G (fifth generation) or 6G (sixth generation), known as next-generation communication standards, are in demand. In these new substrates, extremely high processing speeds, which were not previously required, are now being demanded. Also, extremely high frequencies are being used. In substrates compatible with such next-generation communication standards, when achieving high processing speeds and when using high frequencies, the dielectric properties of the substrate, particularly the dielectric tangent and transmission loss, become problems. If the dielectric properties of the substrate are not sufficient, high processing speeds cannot be achieved and high frequencies cannot be used. Therefore, substrates for next-generation communication standards require excellent dielectric properties. In particular, low dielectric tangent and low transmission loss are required.

[0006] The dielectric properties of the substrate greatly depend on the thermosetting resin composition used for the substrate. In particular, the thermosetting resin and the additives added to the resin greatly affect the dielectric tangent and transmission loss. Therefore, the thermosetting resin composition used for substrates compatible with next-generation communication standards requires excellent dielectric properties that were not required for the thermosetting resin compositions for previous printed circuit boards. It is known that the dielectric loss in a printed circuit board is proportional to the product of the square root of the relative permittivity and the dielectric tangent. In this specification, the product of the square root of the relative permittivity and the dielectric tangent is referred to as the "transmission loss contribution degree". A low transmission loss contribution degree is desired for the materials of the substrates for next-generation communication standards. This need for such excellent dielectric properties was not recognized at all during the technological development of Patent Documents 1 and 2 mentioned above.

[0007] In addition, high heat resistance is also desired for substrates for next-generation communication standards.

[0008] As a resin capable of achieving the dielectric properties and heat resistance required for a substrate for such next-generation communication standards, an acrylic-modified polyphenylene ether resin has attracted attention in place of conventional epoxy resins.

[0009] However, no thermosetting resin composition capable of solving the above-described problem of heat resistance reduction has been known. Furthermore, no thermosetting resin composition capable of manufacturing a substrate having excellent dielectric properties and high heat resistance, which is required for a substrate for next-generation communication standards as described above, has been known. In particular, no modifier suitable for adding to a resin having an ethylenically unsaturated bond such as an acrylic-modified polyphenylene ether resin has been known. For example, in Patent Document 2 above, it has been an issue to provide an unsaturated group-containing phosphate ester that is less likely to undergo hydrolysis during emulsion polymerization or suspension polymerization, and only the solution of that issue has been disclosed. Therefore, the issue of achieving excellent dielectric properties and high heat resistance has not been recognized in Patent Document 2 and has not been assumed at all. Furthermore, Patent Documents 1 and 2 above have not disclosed or suggested at all what kind of modifier is effective for adding to an acrylic-modified polyphenylene ether resin to achieve excellent dielectric properties and high heat resistance. Therefore, no thermosetting resin composition capable of manufacturing a high-frequency printed circuit board having excellent dielectric properties and high heat resistance corresponding to next-generation communication standards has been known.

Prior Art Documents

Patent Documents

[0010]

Patent Document 1

Patent Document 2

Summary of the Invention

Problems to be Solved by the Invention

[0011] The present invention aims to provide a compound that can be used as a modifier for a printed circuit board having excellent dielectric properties and high heat resistance, which are required for a substrate for the next-generation communication standard, a modifier for a printed circuit board, and a thermosetting resin composition.

Means for Solving the Problems

[0012] As a result of intensive research to solve the new problems related to the printed circuit board accompanying the above next-generation communication standard, the inventor has found that a phosphate ester compound having a specific structure solves the above problems and has completed the present invention.

[0013] Specifically, according to the present invention, for example, the following are provided.

[0014] (Item 1) A compound represented by the following formula (I):

Chemical formula

Chemical formula

[0015] (Item 2) The compound according to Item 1 above, where m is 2, or m is 1 and R 4 is C 3 ~C 12 a linear or branched alkenyl group of, Compound.

[0016] (Item 3) R 1 and R 2 are the alkyl group at the 2-position and the alkyl group at the 6-position, and R 3 is a hydrogen atom, the compound according to Item 1 or 2 above.

[0017] (Item 4) R 1 and R 2 are the methyl group at the 2-position and the methyl group at the 6-position, and R 3The compound according to item 3 above, wherein it is a hydrogen atom.

[0018] (Item 5) In the formula (I), R 4 is C 2 ~C 12 The compound according to any one of items 1 to 4 above, which is a linear or branched alkenyl group.

[0019] (Item 6) R 4 is C 3 ~C 12 The compound according to any one of items 1 to 5 above, which is a linear or branched alkenyl group.

[0020] (Item 7) In the formula (I), R 4 is the following formula (III):

Chemical formula

[0021] (Item 8) The compound according to item 7 above, wherein k is an integer of 1 or more and 10 or less.

[0022] (Item 9) The compound according to item 7 or 8 above, wherein m is 1.

[0023] (Item 10) A modifier containing the compound according to any one of items 1 to 9 above.

[0024] (Item 11) A modifier for use in a thermosetting resin composition, The modifier consists of a compound represented by the following formula (I):

Chemical formula

[0025] (Item 12) A thermosetting resin composition comprising a compound according to any one of Items 1 to 9 above, or a modifier according to Item 10 or 11 above, and a thermosetting resin.

[0026] (Item 13) The thermosetting resin composition according to Item 12 above, wherein the thermosetting resin includes a thermosetting resin having an ethylenically unsaturated bond.

[0027] (Item 14) The thermosetting resin composition according to Item 12 or 13 above, wherein the thermosetting resin includes a polyphenylene ether resin modified with an ethylenically unsaturated group.

[0028] (Item 15) The thermosetting resin composition according to any one of Items 12 to 14 above, further comprising a crosslinking agent having an ethylenically unsaturated bond.

[0029] (Item 16) The thermosetting resin composition according to Item 15 above, wherein the crosslinking agent is triallyl isocyanurate.

[0030] (Item 17) The thermosetting resin composition according to any one of Items 12 to 16 above, for manufacturing an insulating layer in a printed circuit board for high frequencies.

[0031] (Item 18) A resin material obtained by curing the thermosetting resin composition according to any one of Items 12 to 17 above.

[0032] (Item 19) A printed circuit board for high frequencies comprising a conductor layer and an insulating layer, wherein the insulating layer includes the resin material according to Item 18 above.

[0033] (Item 20) A method for manufacturing a printed circuit board for high frequencies comprising a conductor layer and an insulating layer, the method including a step of curing the thermosetting resin composition according to Item 17 above to form the insulating layer. [Effect of the Invention]

[0034] According to the present invention, there are provided a compound that can be used as a modifier for a printed circuit board excellent in heat resistance, a modifier for a printed circuit board, and a thermosetting resin composition. Further, according to the present invention, there are provided a compound that can be used as a modifier for a printed circuit board having excellent dielectric properties and high heat resistance required for a substrate for the next-generation communication standard, a modifier for a printed circuit board, and a thermosetting resin composition. [Embodiments for Carrying Out the Invention]

[0035] According to the present invention, there is provided a phosphoric acid ester compound having an ethylenically unsaturated bond. Details thereof will be described below.

[0036] [Compound] The compound of the present invention is represented by the following general formula (I). [Chemical Formula] In formula (I), m is 2 or 1. That is, this compound has two R 4 groups and one phenyl group, or one R 4 group and two phenyl groups.

[0037] Among the five carbons at the 2nd to 6th positions of the benzene ring, three carbons have R 1 to R 3 present, and the remaining two carbons each have a hydrogen atom.

[0038] R 1 are each independently located at any one of the 2nd to 6th positions of the benzene ring, preferably at any one of the 2nd, 3rd, 5th, or 6th positions of the benzene ring, more preferably at any one of the 2nd or 6th positions of the benzene ring.

[0039] R 2 are each independently among the 2nd to 6th positions of the benzene ring where R 1It is located at any of the positions where it does not exist, preferably at any of the 2nd, 3rd, 5th or 6th positions of the benzene ring, more preferably at either the 2nd or 6th position of the benzene ring.

[0040] In one preferred embodiment, R 1 and R 2 are both located at any of the 2nd, 3rd, 5th or 6th positions of the benzene ring. In a more preferred embodiment, R 1 and R 2 are located at the 2nd and 6th positions of the benzene ring. In one preferred embodiment, R 1 and R 2 are the same.

[0041] R 1 are each independently a straight-chain or branched-chain alkyl group of C 1 ~C 8 In one embodiment, it is a straight-chain or branched-chain alkyl group of C 1 ~C 4 In one embodiment, R 1 is an alkyl group of C 1 ~C 2 In one embodiment, R 1 is methyl.

[0042] In this specification, "alkyl" refers to a monovalent group formed by removing one hydrogen atom from a saturated aliphatic hydrocarbon (alkane). "Alkylene" refers to a divalent group formed by further removing one hydrogen atom from alkyl. Also, in this specification, "alkenyl" refers to a structure in which one of the single bonds in alkyl becomes a double bond. That is, alkenyl has one double bond. In the description of each substituent in this specification, when the alkyl group, alkylene group or alkenyl group is branched, its carbon number is 3 or more. For example, "a straight-chain or branched-chain alkyl group of C 1 ~C 4 " means "a straight-chain alkyl group of C 1 ~C 4 or a branched-chain alkyl group of C 3 ~C4 means a branched-chain alkyl group. Also, for example, "C 2 ~C 12 linear or branched-chain alkenyl group" means "C 2 ~C 12 linear alkenyl group or C 3 ~C 12 branched-chain alkenyl group".

[0043] R 2 is each independently a linear or branched-chain alkyl group of C 1 ~C 4 . In one embodiment, it is an alkyl group of C 1 ~C 2 . In one embodiment, R 2 is methyl. R 2 may be the same as or different from R 1 .

[0044] R 3 is each independently located at any one of the three carbons among the five carbons at the 2nd to 6th positions of the benzene ring where R 1 and R 2 do not exist. R 3 is a hydrogen atom or a linear or branched-chain alkyl group of C 1 ~C 8 . In one embodiment, it is a hydrogen atom or a linear or branched-chain alkyl group of C 1 ~C 4 . In one embodiment, R 3 is hydrogen or a C 1 ~C 2 alkyl group. In one embodiment, R 3 is hydrogen or methyl. In one embodiment, R 3 is hydrogen. When R 3 is a hydrogen atom, an alkyl group exists only at two of the five carbons at the 2nd to 6th positions of the benzene ring, and hydrogen exists at the remaining three carbons.

[0045] R 4 is each independently C2 ~C 12 is a linear or branched alkenyl group, or a substituent having the structure of the following formula (II):

Chemical formula

[0046] In one embodiment, R 4 is a substituent of formula (II) only when m is 2.

[0047] R 5 are each independently a hydrogen atom or a methyl group.

[0048] R 6 is, independently of each other, a straight-chain or branched-chain alkylene of C 2 ~C 4 and, in one embodiment, is an alkylene of C 2 (-CH 2 CH 2 -).

[0049] n is an integer from 1 to 5 and, in one embodiment, is 1.

[0050] In one embodiment, R 4 is a substituent having the structure of the following formula (III):

Chemical formula

[0051] In a preferred embodiment of the present invention, m is 1 and R 4 is a substituent having the structure of formula (III). In a more preferred embodiment, k in formula (III) is 1. In a particularly preferred embodiment, m is 1, R 4 is a substituent having the structure of formula (III), k is 1, R 1 and R 2 are a methyl group at the 2-position and a methyl group at the 6-position, and R 3 is a hydrogen atom. If a compound in which m is 1 and R 4 is a substituent having the structure of formula (III) is used as a modifier, a composition excellent in both heat resistance and dielectric properties can be obtained.

[0052] In one embodiment of the present invention, m is 1 and R1 and R 2 is the methyl group at the 2-position and the methyl group at the 6-position, and when R 3 is a hydrogen atom, R 4 is not a vinyl group.

[0053] <Synthesis method of compound> The compound represented by formula (I) can be produced by appropriately combining processes conventionally known as methods for synthesizing phosphate esters.

[0054] In formula (I), when m = 1 and R 4 is alkenyl, the compound can be obtained, for example, by reacting the corresponding alkyl-substituted phenol, phosphorus oxychloride, and alkenyl alcohol. Specifically, for example, phosphorus oxychloride is reacted with the corresponding alkyl-substituted phenol to synthesize di(alkyl-substituted phenyl)phosphorochloridate, and then the obtained di(alkyl-substituted phenyl)phosphorochloridate is reacted with alkenyl alcohol.

[0055] In formula (I), when m = 2 and R 4 is alkenyl, the compound can be obtained, for example, by reacting phosphorus oxychloride with the corresponding alkyl-substituted phenol to synthesize mono(alkyl-substituted phenyl)phosphorodichloridate, and then reacting the obtained mono(substituted phenyl)phosphorodichloridate with alkenyl phenol.

[0056] For example, in formula (I), when m = 1 and R 4 is the substituent of formula (II), the compound can be produced by the method described in JP-A-2003-221415.

[0057] Also, in formula (I), when m = 2 and R 4 is the substituent of formula (II), the compound can be produced by applying the method described in JP-A-2003-221415. Specifically, for example, phosphorus oxychloride is reacted with the corresponding alkyl-substituted phenol to synthesize mono(alkyl-substituted phenyl)phosphorodichloridate, and then the obtained mono(substituted phenyl)phosphorodichloridate is reacted with a (meth)acrylate containing a hydroxyl group to obtain it.

[0058] In the present invention, the above compound can be used as a modifier as it is.

[0059] <Thermosetting resin composition> The thermosetting resin composition of the present invention contains a thermosetting resin and the above modifier.

[0060] <Thermosetting resin> In the thermosetting resin composition of the present invention, a conventionally known thermosetting resin can be used. In one preferred embodiment, a thermosetting resin having an ethylenically unsaturated bond is used.

[0061] In this specification, the ethylenically unsaturated bond means an aliphatic double bond or triple bond capable of undergoing radical polymerization in the presence of a radical. As groups having such unsaturated bonds, various substituents such as acryloyl group, methacryloyl group, vinyl group, allyl group, maleimide group are well known. Resins obtained by bonding these groups having unsaturated bonds to a resin become thermosetting resins having an ethylenically unsaturated bond and can thus be preferably used in the present invention.

[0062] As the thermosetting resin having an ethylenically unsaturated bond, conventionally known ones can be used. For example, polyphenylene ether resins modified with ethylenically unsaturated groups, maleimide resins, styrene resins, etc. can be used.

[0063] <Polyphenylene ether resin modified with an ethylenically unsaturated group> In one embodiment, the thermosetting resin is a polyphenylene ether resin modified with an ethylenically unsaturated group. The polyphenylene ether resin modified with an ethylenically unsaturated group is a resin in which an ethylenically unsaturated group is bonded to the terminal of the polyphenylene ether resin.

[0064] The polyphenylene ether resin modified with an ethylenically unsaturated group is represented by, for example, the following general formula A.

Chemical formula

[0065] In general formula A, an ethylenically unsaturated group is bonded to the hydrogen atom portion of the hydroxyl groups at both ends of the main chain of the polyphenylene ether. Here, in formula A, R 11 ~R 32 are each independently a hydrogen atom or a substituent. Examples of the substituent include a linear or branched alkyl group having 1 to 8 carbon atoms, a linear or branched alkenyl group having 2 to 8 carbon atoms, a linear or branched alkynyl group having 2 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, a carboxyl group, an aldehyde group, a hydroxyl group, an amino group, and the like. X, Y, and Z are each independently a single bond, a carbonyl group (>C=O), a thiocarbonyl group (>C=S), a methylene group (-CH 2 -), an ethylene group (dimethylene group) (-CH 2 -CH 2 -), an isopropenyl group (-C(CH 3 ) 2 -), a trimethylene group (-CH 2 -CH 2 -CH 2 -), or a tetramethylene group (-CH 2 -CH 2 -CH 2 -CH 2 -), etc. n 1 is preferably 1 to 100, more preferably 3 to 20. n 2 is preferably 1 to 100, more preferably 3 to 20.

[0066] In one embodiment, R 16 , R 17 , R 20 , R 21 , R 22 , R 23 , R 26 , and R 27 are hydrogen. In one embodiment, R 14 , R 15 , R 18 , R 19 , R 24 , R 25 , R 28 , and R 29 are alkyl, and in one embodiment, R 14 , R 15 , R 18 , R 19 , R 24 , R 25 , R 28 , and R 29 are methyl.

[0067] In one embodiment, X and Z are carbonyl groups (>C=O), and Y is an isopropenyl group (-C(CH 3 )) 2 -). Also, in one embodiment, X is a benzylene group (-C 6 H 4 CH 2 -), Y is an isopropenyl group (-C(CH 3 )) 2 -), and Z is a benzylene group (-CH 2 C 6 H 4 -).

[0068] In one embodiment, R 13 and R 32 are methyl. In one embodiment, R 13 and R 32 are hydrogen.

[0069] In one embodiment, R 11 , R 12 , R 30 and R 31 are hydrogen.

[0070] The molecular weight of the polyphenylene ether resin modified with an ethylenically unsaturated group is not particularly limited. For example, a number average molecular weight of 500 or more is preferable, and 1,000 or more is more preferable. Also, for example, a number average molecular weight of 10,000 or less is preferable, 7,000 or less is more preferable, and in one embodiment it is 5,000 or less. In one embodiment, it is 3,000 or less. When the molecular weight is too small, the Tg of the cured product tends to be low and the heat resistance tends to decrease. When the molecular weight is too large, the fluidity decreases, and it may be difficult to mold the cured product.

[0071] Specific preferable resins include, for example, those having the following structures.

Chemical formula

[0072] As a specific product of the resin having such a structure, for example, Noryl (registered trademark) SA9000 resin manufactured by SABIC Japan Co., Ltd. is commercially available. Also, those having the following structure can also be used as preferable resins.

Chemical formula

[0073] <Maleimide resin> In one embodiment, a maleimide resin can also be used as the thermosetting resin. Any known maleimide resin can be used. Specifically, for example, 4,4'-bismaleimidodiphenylmethane, N,N'-p-phenylenebismaleimide, N,N'-m-phenylenebismaleimide, N,N'-m-phenylenebismaleimide, bisphenol A diphenyl ether bismaleimide, 3,3'-dimethyl-5,5'-diethyl-4,4'-diphenylmethane bismaleimide, 1,6'-bismaleimide-(2,2,4-trimethyl)hexane, N,N'-(sulfonyldi-p-phenylene)dimaleimide can be mentioned.

[0074] <Styrene resin> In one embodiment, as the thermosetting resin, a corresponding styrene resin having an allyl group bonded to the side chain of polystyrene can also be used. For example, polymers having a structural unit represented by the following formula in the molecule are known and can be used in the present invention.

Chemical formula

[0075] <Other resins> In the thermosetting resin composition of the present invention, if necessary, in addition to the thermosetting resin having an ethylenically unsaturated bond, a thermosetting resin having no ethylenically unsaturated bond can also be used.

[0076] For example, an epoxy resin can be used. However, in order to fully exhibit the effects of the present invention, it is preferable to use a small amount of a thermosetting resin having no ethylenically unsaturated bond. The amount of the thermosetting resin having no ethylenically unsaturated bond is preferably 50 parts by mass or less, more preferably 30 parts by mass or less, and even more preferably 10 parts by mass or less with respect to 100 parts by mass of the thermosetting resin having an ethylenically unsaturated bond.

[0077] In the thermosetting resin composition of the present invention, if necessary, in addition to the thermosetting resin, a thermoplastic resin can also be used. However, in order to fully exhibit the effects of the present invention, it is preferable to use a small amount of the thermoplastic resin. The amount of the thermoplastic resin is preferably 50 parts by mass or less, more preferably 30 parts by mass or less, and even more preferably 10 parts by mass or less with respect to 100 parts by mass of the thermosetting resin having an ethylenically unsaturated bond. In one embodiment, the thermosetting resin composition of the present invention does not contain a thermoplastic resin.

[0078] <Crosslinking agent> The thermosetting resin composition of the present invention optionally contains a monomer compound having an ethylenically unsaturated bond as a crosslinking agent. The crosslinking agent having an ethylenically unsaturated bond copolymerizes with the thermosetting resin having an ethylenically unsaturated bond during the thermosetting reaction, and provides good physical properties to the resulting cured product.

[0079] As the crosslinking agent, monomers known as crosslinking agents for thermosetting resins having an ethylenically unsaturated bond can be used. For example, triallyl isocyanurate, triallyl cyanurate, diallyl phthalate, styrene, etc. can be used. A monomer having two or more ethylenically unsaturated bonds in one molecule is preferable, and a monomer having three or more ethylenically unsaturated bonds in one molecule is more preferable. Also, a monomer having four or less ethylenically unsaturated bonds in one molecule is preferable. In one embodiment, the crosslinking agent is a monomer having three ethylenically unsaturated bonds in the molecule.

[0080] Examples of the portion having an ethylenically unsaturated bond in the crosslinking agent include an allyl group, an acryloyl group, a methacryloyl group, etc. The allyl group is preferred. The molecular weight of the crosslinking agent is preferably 100 or more, more preferably 200 or more. The molecular weight of the crosslinking agent is preferably 700 or less, more preferably 500 or less, and even more preferably 300 or less.

[0081] The amount of the crosslinking agent used is not particularly limited. The amount of the crosslinking agent used is preferably 1 part by mass or more, more preferably 3 parts by mass or more, even more preferably 5 parts by mass or more, and particularly preferably 10 parts by mass or more with respect to 100 parts by mass of the thermosetting resin having an ethylenically unsaturated bond in the thermosetting resin composition. If necessary, it is also possible to make it 20 parts by mass or more, and it is also possible to make it 30 parts by mass or more with respect to 100 parts by mass of the thermosetting resin having an ethylenically unsaturated bond.

[0082] The amount of the crosslinking agent used is preferably 200 parts by mass or less, more preferably 150 parts by mass or less, and even more preferably 100 parts by mass or less with respect to 100 parts by mass of the thermosetting resin having an ethylenically unsaturated bond in the thermosetting resin composition. If necessary, it is also possible to make it 120 parts by mass or less, and it is also possible to make it 100 parts by mass or less with respect to 100 parts by mass of the thermosetting resin having an ethylenically unsaturated bond.

[0083] When the amount of the crosslinking agent used is too small, sufficient heat resistance may be difficult to obtain in the cured product obtained by curing the thermosetting resin composition. When the amount of the crosslinking agent used is too large, sufficient tensile strength and impact strength may not be obtained in the cured product obtained by curing the thermosetting resin composition.

[0084] Note that although the modifier compound having an ethylenically unsaturated bond can also function as a crosslinking agent, in the present invention, the modifier compound having an ethylenically unsaturated bond exhibits a remarkable effect as a modifier. Therefore, in this specification, the modifier compound having an ethylenically unsaturated bond is not included in the crosslinking agent.

[0085] <Radical generator> The thermosetting resin composition of the present invention contains a radical generator, if necessary. The radical generator may generate radicals when heated, or may generate radicals by irradiation with light (for example, visible light or ultraviolet light).

[0086] As the radical generator, any compound known as a radical polymerization initiator for a compound having an ethylenically unsaturated bond can be used. For example, peroxide-based initiators, azo-based initiators, etc. can be used.

[0087] The amount of the radical generator used is preferably 0.01 part by mass or more, more preferably 0.05 part by mass or more, still more preferably 0.1 part by mass or more, and particularly preferably 0.5 part by mass or more with respect to 100 parts by mass of the total amount of the compounds having an ethylenically unsaturated bond in the thermosetting resin composition. The amount of the radical generator used is preferably 10 parts by mass or less, more preferably 5 parts by mass or less, and still more preferably 3 parts by mass or less with respect to 100 parts by mass of the total amount of the compounds having an ethylenically unsaturated bond in the thermosetting resin composition. When the amount of the radical generator used is too small, it is likely to be difficult to sufficiently cure the thermosetting resin composition. When the amount of the radical generator used is too large, the physical properties of the cured product obtained by curing the thermosetting resin composition as a resin material may not be sufficient.

[0088] <Modifier> In the thermosetting resin composition of the present invention, the above-described phosphate ester compound having an ethylenically unsaturated bond is used as a modifier. In this specification, "modification" means improving the properties of a resin, and a "modifier" means a compound added to a resin to improve the properties of the resin. The modifier of the present invention is effective for improving the properties of a thermosetting resin, and in particular, is effective for improving the properties of a thermosetting resin having an ethylenically unsaturated bond. In one embodiment, the modifier of the present invention can improve the dielectric properties of a thermosetting resin composition. The modifier of the present invention is effective for improving either the dielectric tangent or the transmission loss of a thermosetting resin composition, and is also effective for improving both the dielectric tangent and the transmission loss. Therefore, the modifier of the present invention can be suitably used for a thermosetting resin composition for a printed circuit board. It can be preferably used particularly for a printed circuit board for high frequencies. Further, the modifier of the present invention can maintain the high heat resistance of a thermosetting resin composition.

[0089] The amount of the modifier used is not particularly limited. The amount of the modifier used is preferably 1 part by mass or more, more preferably 3 parts by mass or more, still more preferably 5 parts by mass or more, and particularly preferably 10 parts by mass or more with respect to 100 parts by mass of the thermosetting resin having an ethylenically unsaturated bond in the thermosetting resin composition. If necessary, it is also possible to use 20 parts by mass or more, or 30 parts by mass or more with respect to 100 parts by mass of the thermosetting resin having an ethylenically unsaturated bond.

[0090] The amount of the modifier used is preferably 50 parts by mass or less, more preferably 40 parts by mass or less, and still more preferably 30 parts by mass or less with respect to 100 parts by mass of the thermosetting resin having an ethylenically unsaturated bond in the thermosetting resin composition. If necessary, it is also possible to use 20 parts by mass or less, or 10 parts by mass or less with respect to 100 parts by mass of the thermosetting resin having an ethylenically unsaturated bond. When the amount of the modifier used is too small or too large, sufficient physical properties may not be obtained in the cured product obtained by curing the thermosetting resin composition.

[0091] <Reinforcing material> In the thermosetting resin composition of the present invention, a reinforcing material can be used as needed.

[0092] As the reinforcing material, any known material as a reinforcing material for thermosetting resins can be used. For example, fibrous reinforcing materials conventionally used as reinforcing materials for epoxy resins can be used. Specifically, for example, glass fibers can be used.

[0093] The reinforcing material may be one that can be uniformly mixed in the thermosetting resin composition, or one that cannot be mixed. Examples of the reinforcing material that can be uniformly mixed in the thermosetting resin composition include short glass fibers, and examples of the reinforcing material that cannot be uniformly mixed in the thermosetting resin composition include long glass fibers.

[0094] For example, a glass fiber in the form of a sheet or mat can be impregnated with the thermosetting resin composition and used as a molding material in the form of a so-called prepreg.

[0095] The amount of the reinforcing material used is not particularly limited. Specifically, for example, based on 100 parts by mass of the total amount of the thermosetting resin, crosslinking agent, radical generator, and modifier in the thermosetting resin composition, the amount of the reinforcing material can be 1 part by mass or more, 10 parts by mass or more, 30 parts by mass or more, or 50 parts by mass or more. Also, based on 100 parts by mass of the total amount of the thermosetting resin, crosslinking agent, radical generator, and modifier in the thermosetting resin composition, the amount of the reinforcing material can be 300 parts by mass or less, 200 parts by mass or less, 150 parts by mass or less, or 100 parts by mass or less.

[0096] <Other additives> In the thermosetting resin composition of the present invention, various additives other than the above-mentioned modifier and reinforcing material can be further blended within a range that does not affect the effects of the present invention, according to the properties desired for the resin composition. For example, known flame retardants, flame retardant aids, ultraviolet absorbers, antioxidants, light stabilizers, colorants (e.g., dyes or pigments), surface modifiers, antibacterial agents, insect repellants, antistatic agents, fillers (e.g., inorganic fillers), etc. can be added.

[0097] There are no particular limitations on the types and amounts of these additives, and commonly used additives can be used within the range of normal usage amounts. Specifically, for example, for each of these additives, it is possible to use 0.01 part by mass or more, 0.1 part by mass or more, or 1 part by mass or more with respect to 100 parts by mass of the thermosetting resin, and it is possible to use 20 parts by mass or less, 10 parts by mass or less, or 5 parts by mass or less.

[0098] However, additives such as the above-mentioned colorants, ultraviolet absorbers, hydrolysis inhibitors, fillers, etc. are not necessarily required in the thermosetting resin composition of the present invention. It is sufficient to use the thermosetting resin composition in the minimum necessary amount based on the performance required for the product manufactured from the target thermosetting resin.

[0099] <Method for preparing the composition> The operations of mixing and stirring in the preparation of the thermosetting resin composition can be carried out using conventional stirring devices, such as various mills, Henschel mixers (FM mixers), etc. As long as various components can be uniformly mixed, the order of addition does not matter. All components can be put into the stirring device at once for mixing and stirring. For example, a procedure can be adopted in which materials other than the radical generator are mixed first, and then the radical generator is mixed later.

[0100] <Thermosetting reaction> In the thermosetting resin composition of the present invention, the curing reaction can be carried out by a conventionally known method. For example, if heat is applied to a radical generator or light is irradiated to generate radicals, the generated radicals cause a polymerization reaction of the ethylenically unsaturated bonds of the thermosetting resin to obtain a cured product of the resin. Further, if a crosslinking agent is contained in the thermosetting resin composition, a polymerization reaction occurs between the ethylenically unsaturated bond of the thermosetting resin and the ethylenically unsaturated bond of the crosslinking agent to obtain a cured product of the resin. Further, since the compound and the modifier of the present invention also have an ethylenically unsaturated group, a polymerization reaction of the compound and the modifier of the present invention occurs due to radicals.

[0101] The conditions for curing the thermosetting resin composition are appropriately selected according to the type and amount of the radical generator used. For example, if a radical generator that decomposes relatively rapidly at room temperature to generate radicals is used, room temperature may be used. When a radical generator that cannot be decomposed rapidly unless at a high temperature is used, a high temperature is used. Specifically, the temperature when curing the thermosetting resin composition can be, for example, 80°C or higher, or 100°C or higher, and can also be, for example, 250°C or lower, or 230°C or lower. Further, the heating time can be, for example, 1 minute or longer or 3 minutes or longer, and can also be, for example, 120 minutes or shorter or 90 minutes or shorter.

[0102] When a curing reaction is carried out in the thermosetting resin composition of the present invention, it is considered that a copolymer containing a residue of a thermosetting resin having an ethylenically unsaturated bond and a residue of the compound or modifier of the present invention is formed. Further, when a curing reaction is carried out by including a crosslinking agent in the thermosetting resin composition of the present invention, it is considered that a copolymer containing a residue of a thermosetting resin having an ethylenically unsaturated bond, a residue of the compound or modifier of the present invention, and a residue of the crosslinking agent is formed. Since the dielectric properties and heat resistance of the copolymer thus formed are excellent, it is understood that the substrate produced using the thermosetting resin composition of the present invention has excellent dielectric properties and heat resistance. The cured product obtained by carrying out a curing reaction in the thermosetting resin composition of the present invention has excellent dielectric properties and heat resistance, and thus can be preferably used as a material for manufacturing a printed circuit board. In the present specification, the "resin material" refers to a cured product obtained by carrying out a curing reaction in a thermosetting resin composition and is a material that can be used for various applications. In addition, in the chemical structure of the resin in the cured product, it is presumed that a radical polymerization reaction occurs at the ethylenically unsaturated bond portion in the molecules of each component in the thermosetting resin composition, resulting in a structure in which a plurality of molecules are bonded. However, it is difficult to precisely specify the chemical structure. In particular, when there are multiple types of molecules having ethylenically unsaturated bonds, both homopolymerization and copolymerization may occur, so it is difficult to precisely specify the chemical structure of the product. Even if it is theoretically possible, it requires a great deal of cost and time and is not practical. Therefore, the composition of the thermosetting resin composition before the curing reaction is specified, and the cured product obtained by curing the composition is described by the so-called product-by-process expression.

[0103] <Molded article> The thermosetting resin composition of the present invention can be molded by any method known as a molding method for thermosetting resins. By using a molding machine, a mold, etc. according to the desired molded product, the desired molded product can be easily obtained. For example, by a method such as a heating press, it is possible to perform molding and the curing reaction of the thermosetting resin to obtain the desired molded product. In the thermosetting resin composition, the step of performing the curing reaction and the step of molding into the desired shape may be performed simultaneously or separately. The cured product obtained by performing the curing reaction first may be molded, or the curing reaction may be performed after performing the molding step first.

[0104] The obtained molded product has excellent dielectric properties and has the advantage that the decrease in heat resistance due to the addition of the modifier is small.

[0105] <Printed circuit board> By curing the thermosetting resin composition containing the above-described thermosetting resin and modifier, a substrate usable for a printed circuit board can be obtained. A printed circuit board usually has a conductor layer and an insulating layer. The modifier and the thermosetting resin composition of the present invention can be used to form the insulating layer of the printed circuit board.

[0106] In this specification, the high frequency is not particularly limited, but is preferably 100 MHz or more, in one embodiment is 1 GHz or more, and in another embodiment is 10 GHz or more. Further, the high frequency may be, for example, 100 GHz or less, or 50 GHz or less. In this specification, a printed circuit board for high frequencies means a printed circuit board in which such a high frequency is used.

[0107] In a printed circuit board for high frequencies, high heat resistance is required. If a substrate is manufactured using the thermosetting resin of the present invention, excellent heat resistance can be achieved. Further, if a substrate is manufactured using the thermosetting resin of the present invention, excellent dielectric properties and heat resistance can be achieved, so it can be suitably used for a printed circuit board for high frequencies.

Examples

[0108] The present invention will be described more specifically by the following examples, but the present invention is not limited to the following examples.

[0109] (Raw materials) In the following synthesis examples, the following compounds were used as raw materials. · Phosphorus oxychloride (manufactured by Tokyo Chemical Industry Co., Ltd.) · 2,6-Dimethylphenol (manufactured by Tokyo Chemical Industry Co., Ltd.) · Triethylamine (manufactured by Tokyo Chemical Industry Co., Ltd.) · Allyl alcohol (manufactured by Tokyo Chemical Industry Co., Ltd.)

[0110] (Synthesis Example 1A) Synthesis of Monoxilyl Phosphorodichloridate (MXPC) A 2-liter four-necked flask equipped with a stirrer, a thermometer, and a hydrochloric acid recovery device (a condenser connected to a water scrubber) was charged with 1500 g of phosphorus oxychloride, 611 g of 2,6-dimethylphenol, and 1.2 g of magnesium chloride as a catalyst.

[0111] While stirring the obtained mixed solution, the temperature was gradually raised to 110°C over about 3 hours for reaction, and the generated hydrogen chloride (hydrochloric acid gas) was recovered with a water scrubber. Then, the pressure in the flask was gradually reduced to 12 kPa at 120°C to remove unreacted phosphorus oxychloride, phenol, and by-produced hydrogen chloride, and 1200 g of a reaction mixture mainly composed of monophenyl phosphorodichloridate having the following structural formula was obtained. Also, the chlorine content of the reaction mixture was 28.3% by mass. [Chemical formula]

[0112] (Synthesis Example 1B) Compound (1) A 0.5-liter four-necked flask equipped with a stirrer, a thermometer, a dropping funnel, and a condenser was charged with 34.8 g of allyl alcohol, 60.7 g of triethylamine as a hydrogen halide scavenger, 7.3 g of 4-dimethylaminopyridine as a catalyst, and 200 g of toluene as a solvent. The dropping funnel was also charged with 71.7 g of monoxilyl phosphorodichloridate obtained in Synthesis Example 1.

[0113] While stirring the mixed solution in the four-necked flask, the temperature was adjusted to 20 °C, and while maintaining the same temperature (20 °C), the monoxilyl phosphorodichloridate in the dropping funnel was added dropwise over 1 hour. After completion of the dropwise addition, the mixture was stirred at the same temperature for 2 hours to obtain a reaction product. The obtained reaction product was washed with dilute hydrochloric acid and water, neutralized and washed with sodium carbonate and water, heated to 50 °C, reduced in pressure to 2 kPa to distill off water, toluene, and low-boiling components, and cooled to room temperature to obtain 76.2 g of a yellow liquid. The results of NMR measurement were as follows. 1 H-NMR spectrum (400 MHz, CDCl 3 , δ ppm): 7.00 (3H, m), 5.92 (2H, m), 5.35 (2H, d), 5.23 (2H, d), 4.61 (4H, m), 2.36 (6H, m) 31 P-NMR spectrum (400 MHz, CDCl 3 , δ ppm): -0.1, -5.1, -10.3 Also, the phosphorus atom content determined according to ASTM D1091 was 10.70%. From the above analysis results, it was confirmed that this product contained 86.7% of the substance of the following structural formula.

[0114]

Chemical formula

[0115] (Synthesis Example 2) Compound (2) Compound (2) was obtained according to the procedure described in JP-A-2003-221415, paragraphs 0050 to 0052.

Chemical formula

[0116] (Compound (3)) As Compound (3), commercially available resorcinol bis(2,6-xylyl) phosphate (manufactured by Daihachi Chemical Industry Co., Ltd., trade name: PX-200) was used. [Chemical formula]

[0117] (Synthesis Example 3 (Compound (4)) The following formula: [Chemical formula] The compound of was synthesized by the following procedure.

[0118] (Synthesis Example 4A) Synthesis of Dixylyl Phosphorodichloridate (DXPC) A 2-liter four-necked flask equipped with a stirrer, a thermometer, and a hydrochloric acid recovery device (a condenser connected to a water scrubber) was charged with 767 g of phosphorus oxychloride, 1200 g of 2,6-dimethylphenol, 140 g of xylene as a solvent, and 6.2 g of magnesium chloride as a catalyst.

[0119] While stirring the obtained mixed solution, the temperature was gradually raised to 160 °C over about 3 hours to cause a reaction, and the generated hydrogen chloride (hydrochloric acid gas) was recovered with a water scrubber. Then, the pressure inside the flask was gradually reduced to 20 kPa at the same temperature to remove xylene, unreacted phosphorus oxychloride, 2,6-dimethylphenol, and by-produced hydrogen chloride, and 1700 g of a reaction mixture mainly composed of dixylyl phosphorochloridate represented by the following structural formula was obtained. The chlorine content of the reaction mixture was 10.9% by mass. [Chemical formula]

[0120] (Synthesis Example 4B) Compound (4) A 2-liter four-necked flask equipped with a stirrer, a thermometer, a dropping funnel, and a condenser was charged with 487.1 g of dicyxilyl phosphorodichloridate obtained in Synthesis Example A, 151.8 g of triethylamine as a hydrogen halide scavenger, 18.3 g of 4-dimethylaminopyridine as a catalyst, and 500 g of toluene as a solvent. Further, the dropping funnel was charged with 87.1 g of allyl alcohol.

[0121] While stirring the mixed solution in the four-necked flask, the temperature was adjusted to 20 °C, and while maintaining the same temperature (20 °C), the allyl alcohol in the dropping funnel was added dropwise over 1 hour and 30 minutes. After completion of the dropping, the mixture was stirred at the same temperature for 8 hours to obtain a reaction product. The obtained reaction product was washed with dilute hydrochloric acid and water, neutralized and washed with sodium carbonate and water, heated to 50 °C, reduced in pressure to 2 kPa to distill off water, toluene, and low-boiling components, and cooled to room temperature to obtain 508.6 g of a yellow liquid.

[0122] The results of NMR measurement were as follows. 1 H-NMR spectrum (400 MHz, CDCl 3 , δ ppm): 7.00 (6H, m), 5.78 (1H, m), 5.24 (1H, d), 5.14 (1H, d), 4.61 (2H, m), 2.32 (12H, m) 31 P-NMR spectrum (400 MHz, CDCl 3 , δ ppm): -10.3, -15.8, -24.4

[0123] Also, the phosphorus atom content determined according to ASTM D1091 was 8.90%. From the above analysis results, it was confirmed that this product contained 97.2% of the substance of the following structural formula.

Chemical formula

[0124] <Experiment A> (Examples 1A and 2A and Comparative Examples 1A and 2A) The experiments of Example 1A, Example 2A, Comparative Example 1A, and Comparative Example 2A were conducted as follows.

[0125] (Lamination Plate Molding and Physical Property Evaluation) In the examples, the following compounds were used as raw materials. · Resin: Methacrylic-modified polyphenylene ether resin (SA-9000 manufactured by SABIC, a polyphenylene ether resin whose ends are modified with methacrylic acid, two terminal methacryloyl groups) · Crosslinking agent: Triallyl isocyanurate (manufactured by Tokyo Chemical Industry Co., Ltd.) · Radical initiator: 1,3-bis(t-butylperoxyisopropyl)benzene (Perbutyl P manufactured by NOF Corporation)

[0126] (Preparation and Physical Property Evaluation of Resin Composition) A thermosetting resin composition was prepared by blending various components at the ratios shown in Table 1, and 1.3 g of the resin composition was impregnated into 2.0 g of a glass cloth with a basis weight of 100 g / m 2 and dried at room temperature for 10 minutes and in a 120°C oven for 3 minutes to obtain a prepreg. Next, 8 sheets of this prepreg were stacked, sandwiched between stainless steel mirror plates, and cured at a temperature of 210°C and a press pressure of 3 MPa for 60 minutes using a hot press to obtain a sample of the laminated plate.

[0127] (Test Method) Glass transition temperature: According to JIS K 7244, using a dynamic viscoelasticity measuring device manufactured by Hitachi High-Technologies Corporation, in bending mode, under a nitrogen atmosphere, at a measurement frequency of 10 Hz and a heating rate of 5°C / min, it was determined from the loss factor (tanδ).

[0128]

Table 1

[0129] The glass transition temperatures in Example 1A and Example 2A were higher than those in Comparative Example 2A, and it was confirmed that the decrease in the glass transition temperature due to the addition of the modifier was small. From this, it was confirmed that the decrease in heat resistance due to the addition of the modifier was small.

[0130] <Experiment B> The experiments of Example 1B, Example 2B and Example 3, and Comparative Example 1B and Comparative Example 2B were conducted as follows in a facility different from the facility where Experiment A was conducted.

[0131] (Example 1B and 2B, and Comparative Example 1B and 2B) The same experiments as in Example 1B and 2A, and Comparative Example 1A and 2A were conducted again. The results are shown in Table 2 below.

Table 2

[0132] The glass transition temperatures in Example 1B and Example 2B were higher than those in Comparative Example 2B, and it was confirmed that the decrease in the glass transition temperature due to the addition of the modifier was small. From this, it was confirmed that the decrease in heat resistance due to the addition of the modifier was small.

[0133] (Example 3 and Comparative Example 1B - 2B) (Laminated Plate Molding and Physical Property Evaluation) In Example 3, the following compounds were used as raw materials. · Resin: Methacrylic acid-modified polyphenylene ether resin (SA-9000 manufactured by SABIC, a polyphenylene ether resin modified with methacrylic acid at the ends, with two terminal methacryloyl groups) · Crosslinking agent: Triallyl isocyanurate (manufactured by Tokyo Chemical Industry Co., Ltd.) · Radical initiator: 1,3-bis(t-butylperoxyisopropyl)benzene (Perbutyl P manufactured by NOF Corporation)

[0134] (Preparation of Resin Composition and Physical Property Evaluation) In Example 3, a thermosetting resin composition was prepared by blending various components at the ratios shown in Table 3, and samples of laminated plates were obtained in the same manner as in Comparative Example 1A and 2A.

[0135] (Test Method) (1) Glass transition temperature: In Example 3, measurements were carried out in the same manner as in Comparative Examples 1A and 2A. The results are shown in Table 3. For Comparative Examples 1B and 2B, the measurement results of the glass transition temperatures of Comparative Examples 1B and 2B described in Table 2 are shown in Table 3 again. (2) Dielectric tangent: The dielectric tangent was measured in the samples of Example 3 and the samples of Comparative Examples 1B and 2B above. Specifically, in accordance with IEC62810, using a PNA network analyzer manufactured by Keysight Technologies Co., Ltd. and a cavity resonator manufactured by Kanto Electronic Application Development Co., Ltd., the dielectric tangent (tanδ) at a frequency of 10 GHz was obtained by the cavity resonator perturbation method. In the table, the addition amounts are in parts by mass respectively.

[0136]

Table 3

[0137] (3) Transmission loss contribution: The transmission loss contribution was determined in the samples of Example 3 and the samples of Comparative Example 1B. Specifically, when measuring the above dielectric tangent (tanδ), the relative permittivity (εr) was further determined. From the obtained values of the dielectric tangent (tanδ) and the relative permittivity (εr), the transmission loss contribution was determined based on the following formula (A).

Equation

[0138]

Table 4

[0139] The glass transition temperature in Example 3 was higher than that in Comparative Example 2B, and it was confirmed that the decrease in the glass transition temperature due to the addition of the modifier was small. Also, in Example 3, excellent dielectric properties were confirmed. That is, it was confirmed that the dielectric tangent and the transmission loss contribution degree were lower than those in Comparative Example 1B, and the dielectric properties were excellent. Therefore, it is understood that the transmission efficiency of the electrical signal is high. From this, in Example 3, it was confirmed that high heat resistance was maintained in the cured product and the decrease in heat resistance due to the addition of the modifier was small.

[0140] From the results of the above Experiments A and B, it was confirmed that high heat resistance can be achieved according to the modifier of the present invention. Also, from the results of the above Experiment B, it was confirmed that excellent dielectric properties and high heat resistance can be achieved simultaneously by using the modifier of the preferred embodiment.

Industrial Applicability

[0141] According to the present invention, there are provided a modifier for a printed circuit board having excellent heat resistance and a thermosetting resin composition. According to the present invention, there are provided a modifier and a thermosetting resin composition particularly suitable for a high-frequency printed circuit board corresponding to the next-generation communication standard. According to the modifier and the thermosetting resin composition of the present invention, there is provided a printed circuit board having high transmission efficiency of electrical signals and excellent heat resistance.

[0142] As described above, the present invention has been exemplified using the preferred embodiments of the present invention, but the present invention should not be construed as being limited to these embodiments. It is understood that the scope of the present invention should be construed only by the claims. Those skilled in the art will understand that an equivalent range can be implemented based on the description of the present invention and common technical knowledge from the description of the specific preferred embodiments of the present invention. It is understood that the patents, patent applications, and documents cited in this specification should be incorporated by reference in their entirety as if the content were specifically described in this specification.

Claims

1. A compound represented by the following formula (I): 【Chemical 1】 In formula (I), m is 2 or 1, R １ is independently located at any one of the 2nd to 6th positions of the benzene ring and is a linear or branched alkyl group of C １ to C ４ ; R ２ is, independently of each other, located at any one of the 2nd to 6th positions of the benzene ring and is a linear or branched alkyl group of C １ to C ４ , which may be the same as or different from R １ and R ３ is independently located at any one of the 2nd to 6th positions of the benzene ring, and is a hydrogen atom, or a linear or branched alkyl group of C １ to C ４ ; R １ may be the same as or different from R ２ may be the same as or different from R, Of the 2nd to 6th positions of the benzene ring, for the two carbons where R １ ~R ３ do not exist, hydrogen atoms exist respectively, When m is 2, R ４ is, independently of one another, C ２ to C １２ linear or branched alkenyl group, or the following formula (II): [Chemical 2] is a substituent having the structure of, In formula (II), R ５ is, independently of one another, a hydrogen atom or a methyl group, R ６ is, independently of one another, C ２ to C ４ linear or branched alkylene, n is an integer from 1 to 5, and When m is 1, R ４ is a linear or branched alkenyl group of C ２ to C １２ and is a linear or branched alkenyl group, However, in formula (I), when m is 1, R1 is a methyl group located at the 2-position of the benzene ring, R2 is a methyl group located at the 6-position of the benzene ring, R3 is a hydrogen atom, and R4 is a vinyl group; and in formula (I), when m is 2, R1 is a methyl group located at the 2-position of the benzene ring, R2 is a methyl group located at the 4-position of the benzene ring, R3 is a hydrogen atom, R4 is a substituent having the structure of formula (II), R5 is a methyl group, R6 is an ethylene group, and n is 1. Excluding these compounds, Compound.

2. The compound according to claim 1, wherein m is 2, or where m is 1 and R ４ is C ３ -C １２ to C, a straight-chain or branched-chain alkenyl group, a compound.

3. R １ and R ２ are the alkyl group at the 2-position and the alkyl group at the 6-position, and R ３ is a hydrogen atom, the compound according to claim 1 or 2.

4. R １ and R ２ are the methyl group at the 2-position and the methyl group at the 6-position, and R ３ is a hydrogen atom, the compound according to claim 3.

5. In the formula (I), R ４ is C ２ to C １２ a linear or branched alkenyl group, and the compound according to claim 1.

6. R ４ is C ３ to C １２ The compound according to any one of claims 1 to 5, which is a linear or branched alkenyl group of C

7. In the formula (I), R ４ is the following formula (III): 【Chemical Formula 3】 is an alkenyl group having the structure of, Here, in the above formula (III), k is an integer from 0 to 10, The compound according to claim 5 or 6.

8. The compound according to claim 7, wherein k is an integer from 1 to 10.

9. The compound according to claim 7 or 8, wherein m is 1.

10. A modifier comprising the compound according to any one of claims 1 to 9.

11. A modifier for use in a thermosetting resin composition, wherein The modifier consists of a compound represented by the following formula (I): 【Chemical 11】 In formula (I), m is 2 or 1, R １ is independently located at any one of the 2nd to 6th positions of the benzene ring and is a linear or branched alkyl group of C １ to C ４ and R ２ is independently located at any one of the 2nd to 6th positions of the benzene ring and is a linear or branched alkyl group of C １ to C ４ , which may be the same as or different from R １ ​ R ３ is independently located at any one of the 2nd to 6th positions of the benzene ring, and is a hydrogen atom or a linear or branched alkyl group of C １ to C ８ , may be the same as or different from R １ , may be the same as or different from R ２ , and may be the same as or different from R Of the 2nd to 6th positions of the benzene ring, for the two carbons where R １ ~R ３ do not exist, hydrogen atoms exist respectively, and R ４ is, independently of one another, a linear or branched alkenyl group of C ２ to C １２ or, R ４ is, independently of one another, the following formula (II): 【Chemical 12】 is a substituent having the structure of, In formula (II), R ５ each independently represents a hydrogen atom or a methyl group, R ６ is, independently of each other, C ２ to C ４ linear or branched alkylene, and n is an integer from 1 to 5, Modifier.

12. A thermosetting resin composition comprising the compound according to any one of claims 1 to 9 or the modifier according to claim 10 or 11, and a thermosetting resin.

13. The thermosetting resin composition according to claim 12, wherein the thermosetting resin comprises a thermosetting resin having an ethylenically unsaturated bond.

14. The thermosetting resin composition according to claim 12 or 13, wherein the thermosetting resin comprises a polyphenylene ether resin modified with an ethylenically unsaturated group.

15. The thermosetting resin composition according to any one of claims 12 to 14, further comprising a crosslinking agent having an ethylenically unsaturated bond.

16. The thermosetting resin composition according to claim 15, wherein the crosslinking agent is triallyl isocyanurate.

17. The thermosetting resin composition according to any one of claims 12 to 16, for manufacturing an insulating layer in a high-frequency printed circuit board.

18. A resin material obtained by curing the thermosetting resin composition according to any one of claims 12 to 17.

19. A high-frequency printed circuit board including a conductor layer and an insulating layer, wherein the insulating layer contains the resin material according to claim 18.

20. A method for manufacturing a high-frequency printed circuit board including a conductor layer and an insulating layer, the method including a step of curing the thermosetting resin composition according to claim 17 to form the insulating layer.

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