JP2021031504A - Thermosetting resin composition, prepreg, laminated sheet, printed wiring board and module adaptive to high-speed communication - Google Patents

Abstract

To provide a thermosetting resin composition that has low thermal expansion and is not only excellent in dielectric characteristics and solder heat resistance in a high frequency band but also excellent in moisture-absorption solder heat resistance and to provide a prepreg, a laminated sheet, a printed wiring board and a module adaptive to high-speed communication, each using the thermosetting resin composition.SOLUTION: The thermosetting resin composition contains: (A) an addition reaction product of (a1) a maleimide compound having at least two N-substituted maleimide groups and (a2) an amine compound having at least two primary amino groups; (B) an acrylic elastomer; and (C) a copolymer resin containing a structural unit derived from an aromatic vinyl compound and a structural unit derived from a carboxylic acid anhydride.SELECTED DRAWING: None

Description

The present invention relates to a thermosetting resin composition, a prepreg, a laminated board, a printed wiring board, and a module compatible with high-speed communication.

With the recent trend toward miniaturization and higher performance of electronic devices, the wiring density of printed wiring boards has become more sophisticated and highly integrated, and along with this, laminated boards for printed wiring boards have become more popular. There is an increasing demand for improved reliability by improving heat resistance. In printed wiring board applications, it is required to have both excellent heat resistance and low thermal expansion.
Further, the communication module is required to process a large amount of information at high speed. Therefore, it is important to speed up signal processing and reduce transmission loss. In recent years, the demand for high-frequency modules has been increasing. Therefore, low dielectric constant and low dielectric loss tangent that enable low transmission loss in the high frequency band. Substrate materials are required.

As a laminated board for a printed wiring board, a prepreg containing a resin composition containing an epoxy resin as a main component and a glass cloth is generally cured and integrally molded.
Epoxy resin has an excellent balance of insulation, heat resistance, cost, etc., but further improvement is required to meet the recent demand for improved heat resistance due to high-density mounting of printed wiring boards and high-multilayer configurations. It becomes. Further, since the epoxy resin has a large coefficient of thermal expansion, low thermal expansion is achieved by selecting an epoxy resin having an aromatic ring and increasing the filling of an inorganic filler such as silica (see, for example, Patent Document 1). However, it is known that increasing the filling amount of the inorganic filler causes deterioration of insulation reliability due to moisture absorption, insufficient adhesion between the resin and the wiring layer, poor press molding, etc., and the filling of the inorganic filler is increased. There was a limit to the low thermal expansion by chisel. Furthermore, when an epoxy resin is used, it is difficult to obtain a cured resin product having a good relative permittivity and dielectric loss tangent (hereinafter, also referred to as dielectric properties), and as a material for high-speed communication, it has dielectric properties. Improvement was sought.

On the other hand, it is known that a modified maleimide resin obtained by modifying a maleimide compound with siloxane diamine has excellent heat resistance and low thermal expansion (see, for example, Patent Document 2). The modified maleimide resin has a low relative permittivity and a low dielectric loss tangent as compared with an epoxy resin, but has not yet achieved excellent dielectric properties in the high frequency band required in recent years.

For the purpose of improving the dielectric properties, a laminated board to which a polybutadiene resin is added as a thermoplastic elastomer has been studied. The laminated plate has excellent dielectric properties, but has drawbacks such as the prepreg having adhesiveness, low compatibility with other thermosetting resins, and a large shrinkage rate during curing. is there.
As a method for improving these, a method using a butadiene-vinyl aromatic compound copolymer has been proposed (see, for example, Patent Document 3), but vinyl is used in order to obtain sufficient compatibility with other thermosetting resins. It is necessary to increase the copolymerization ratio of the aromatic compound, and in that case, there arises a problem that the heat resistance is lowered.

Further, in recent years, with the further thinning of the printed wiring board, the problem that the package warps when the semiconductor element is mounted and packaged has become more remarkable. Warpage is considered to be one of the factors that cause poor connection between a semiconductor element and a printed wiring board, and reduction of warpage is required.
One of the factors that cause the package to warp is the difference in the coefficient of thermal expansion between the semiconductor element and the printed wiring board. In general, the coefficient of thermal expansion of a printed wiring board is larger than the coefficient of thermal expansion of a semiconductor element, and warpage occurs due to thermal history or the like when the semiconductor element is mounted. Therefore, it is required to reduce the coefficient of thermal expansion of the printed wiring board.

As a method for improving the warp, a method of reducing the coefficient of thermal expansion of the base material and the rate of curing shrinkage of the resin composition have been studied. As an example of the approach, a method of using a modified maleimide resin and a thermoplastic elastomer in combination has been proposed (see, for example, Patent Document 4). In Patent Document 4, the thermoplastic elastomer is used for the purpose of reducing the internal stress generated at the time of curing the thermosetting resin composition, which leads to the reduction of the warp of the substrate. Here, when a hydrogenated styrene-based elastomer is used as the thermoplastic elastomer, it exhibits a low relative permittivity and a low dielectric loss tangent because the polarity of the skeleton is very small. Therefore, by using the modified maleimide resin and the hydrogenated styrene-based elastomer in combination, it is possible to achieve both a low curing shrinkage rate and excellent dielectric properties (low relative permittivity and low dielectric loss tangent).

Japanese Unexamined Patent Publication No. 5-148343 International Publication No. 2012/099133 Japanese Unexamined Patent Publication No. 61-23060 Japanese Unexamined Patent Publication No. 2014-24926

However, although the thermosetting resin composition described in Patent Document 4 has no problem in general solder heat resistance, it has heat resistance under severe conditions due to the recent high-density mounting and high-multilayer configuration of printed wiring boards. That is, there is a problem that the solder heat resistance after water absorption is inferior. It is considered that this is because the compatibility between the modified maleimide resin and the thermoplastic elastomer was insufficient according to the study by the present inventors.

In view of these circumstances, the present invention provides a thermosetting resin composition having low thermal expansion property, excellent dielectric properties and solder heat resistance in a high frequency band, and also excellent water absorption solder heat resistance. An object of the present invention is to provide a prepreg, a laminated board, a printed wiring board, and a high-speed communication compatible module using the thermosetting resin composition.

As a result of intensive research to solve the above problems, the present inventors have made a thermosetting resin composition containing a specific modified maleimide resin, an acrylic elastomer, and a specific copolymer resin. If so, they have found that the above problems can be solved, and have completed the present invention.

That is, the present invention provides the following thermosetting resin composition, prepreg, laminated board, printed wiring board, and high-speed communication compatible module.
[1] (A) An addition reaction product of a maleimide compound (a1) having at least two N-substituted maleimide groups and an amine compound (a2) having at least two primary amino groups.
(B) Acrylic elastomer and
(C) A copolymer resin containing a structural unit derived from an aromatic vinyl compound and a structural unit derived from a carboxylic acid anhydride,
A thermosetting resin composition comprising.
[2] The thermosetting resin composition according to the above [1], wherein the component (a2) contains a modified siloxane having a primary amino group at the molecular terminal.
[3] The thermosetting resin composition according to the above [1] or [2], wherein the component (B) has a reactive functional group.
[4] The reactive functional group is at least one selected from the group consisting of an epoxy group, a hydroxyl group, a carboxyl group, an amino group, an amide group, an isocyanato group, an acrylic group, a methacryl group and a vinyl group. 3] The thermosetting resin composition according to the above.
[5] As the component (C), the structural unit derived from the aromatic vinyl compound is the structural unit represented by the following general formula (C-1), and the structural unit derived from the carboxylic acid anhydride is the following general formula (C-1). The thermosetting resin composition according to any one of the above [1] to [4], which contains a copolymer resin which is a structural unit represented by -2).

^{(Wherein, R C1} represents a hydrogen atom or an aliphatic hydrocarbon group having 1 to 5 carbon ^{atoms, R C2} each independently an aliphatic hydrocarbon group or a C1-5 carbon 6-20 Indicates an aromatic hydrocarbon group of. X indicates an integer of 0 to 3.)
[6] Content ratio of the structural unit represented by the general formula (C-1) to the structural unit represented by the general formula (C-2) [(C-1) / (C-2)] ( The thermosetting resin composition according to the above [5], wherein the molar ratio) is 5 to 10.
[7] The above-mentioned [1] to [6], wherein the content of the component (B) is 1 to 50 parts by mass with respect to 100 parts by mass of the resin component in the thermosetting resin composition. Thermosetting resin composition.
[8] The above-mentioned [1] to [7], wherein the content of the component (C) is 2 to 20 parts by mass with respect to 100 parts by mass of the resin component in the thermosetting resin composition. Thermosetting resin composition.
[9] The thermosetting resin composition according to any one of the above [1] to [8], which further contains (D) a curing accelerator.
[10] The thermosetting resin composition according to any one of the above [1] to [9], which further contains (E) an inorganic filler.
[11] The heat according to any one of the above [1] to [10], which further contains (F) a thermoplastic elastomer (however, the component (B) and the component (C) are excluded). Curable resin composition.
[12] A prepreg obtained by impregnating a fiber base material with the thermosetting resin composition according to any one of the above [1] to [11].
[13] A laminated board obtained by laminating and molding the prepreg according to the above [12].
[14] A printed wiring board containing the prepreg according to the above [12] or the laminated plate according to the above [13].
[15] A high-speed communication compatible module including the printed wiring board according to the above [14].

According to the present invention, it is possible to provide a thermosetting resin composition having low thermal expansion property, excellent dielectric properties and solder heat resistance in a high frequency band, and also excellent water absorption solder heat resistance, and the heat. It is possible to provide a prepreg, a laminated board, a printed wiring board, and a high-speed communication compatible module using a curable resin composition.

Hereinafter, one embodiment of the present invention will be described in detail, but the present invention is not limited to the following embodiments.
In the numerical range described in the present specification, the upper limit value or the lower limit value of the numerical range may be replaced with the value shown in the examples. Further, the lower limit value and the upper limit value of the numerical range are arbitrarily combined with the lower limit value and the upper limit value of the other numerical range, respectively.
Further, as for each component and material exemplified in this specification, one kind may be used alone or two or more kinds may be used in combination unless otherwise specified. In the present specification, the content of each component in the composition is the total amount of the plurality of substances present in the composition unless otherwise specified, when a plurality of substances corresponding to each component are present in the composition. Means.
Further, when the illustrated and the embodiments described as preferable are a collection of choices, any number of arbitrary choices can be extracted from the aggregate, and the extracted choices will be described elsewhere. It can also be arbitrarily combined with the mode to be used.
The present invention also includes aspects in which the items described in the present specification are arbitrarily combined.

[Thermosetting resin composition]
The thermosetting resin composition of the present invention
(A) Addition reaction product of a maleimide compound (a1) having at least two N-substituted maleimide groups and an amine compound (a2) having at least two primary amino groups [hereinafter, "(A) modified maleimide" Also called "resin"]
(B) Acrylic elastomer and
(C) A copolymer resin containing a structural unit derived from an aromatic vinyl compound and a structural unit derived from a carboxylic acid anhydride,
It is a thermosetting resin composition containing.
The thermosetting resin composition of the present invention has the above-mentioned structure, and thus has a low thermal expansion property, is excellent in dielectric properties and solder heat resistance in a high frequency band, and is also excellent in water absorption solder heat resistance. Can be provided. Further, the laminated plate obtained by using the thermosetting resin composition of the present invention has a high glass transition temperature.
In the present specification, the “high frequency band” refers to a frequency band of 5 GHz or higher, and the present invention particularly aims to improve the dielectric characteristics at 10 GHz or higher.

<(A) Modified maleimide resin>
The modified maleimide resin (A) is an addition reaction between a maleimide compound (a1) having at least two N-substituted maleimide groups and an amine compound (a2) having _{at least two primary amino groups (-NH 2).} It is a thing. Here, the "N-substituted maleimide group" means a group in which an organic group is substituted for a nitrogen atom in the maleimide group.

(Maleimide compound (a1) having at least two N-substituted maleimide groups)
The maleimide compound (a1) having at least two N-substituted maleimide groups (hereinafter, also referred to as “component (a1)”) is particularly long as it has a structure having at least two N-substituted maleimide groups. A maleimide compound having an aliphatic hydrocarbon group between any two maleimide groups of a plurality of maleimide groups (provided that no aromatic hydrocarbon group is present) [hereinafter, aliphatic hydrocarbons]. Group-containing maleimide compound] and a maleimide compound containing an aromatic hydrocarbon group between any two maleimide groups among a plurality of maleimide groups [hereinafter referred to as an aromatic hydrocarbon group-containing maleimide compound]. ] Etc. can be mentioned. Both the aliphatic hydrocarbon group-containing maleimide compound and the aromatic hydrocarbon group-containing maleimide compound may contain an ether bond. Further, the aromatic hydrocarbon group-containing maleimide compound only needs to contain an aromatic hydrocarbon group between any of two arbitrarily selected combinations of maleimide groups, and is a fat together with the aromatic hydrocarbon group. It may have a group hydrocarbon group.
As the component (a1), either an aliphatic hydrocarbon group-containing maleimide compound or an aromatic hydrocarbon group-containing maleimide compound may be used, or these may be used in combination, but they have low thermal expansion and are dielectric in a high frequency band. From the viewpoint of characteristics, solder heat resistance and water absorption solder heat resistance, an aromatic hydrocarbon group-containing maleimide is preferable.
As the component (a1), a maleimide compound having two N-substituted maleimide groups is more preferable, and a compound represented by the following general formula (a1-1) is further preferable.

^{(Wherein, X A1} is represented by the following general formula (a1-2), (a1-3), a group represented by (a1-4) or (a1-5).)

^{(Wherein, R A1} are each independently, .P1 an aliphatic hydrocarbon group having 1 to 5 carbon atoms is an integer of 0-4.)

(In the formula, ^RA2 is an aliphatic hydrocarbon group having 1 to 5 carbon atoms independently. X ^A2 is an alkylene group having 1 to 5 carbon atoms, an alkylidene group having 2 to 5 carbon atoms, and an ether group. A sulfide group, a sulfonyl group, a carbonyloxy group, a keto group, a single bond or a group represented by the following general formula (a1-3'). Q1 is independently an integer of 0 to 4).

(In the formula, ^RA3 is an aliphatic hydrocarbon group having 1 to 5 carbon atoms independently. X ^A3 is an alkylene group having 1 to 5 carbon atoms, an alkylidene group having 2 to 5 carbon atoms, and an ether group. , A sulfide group, a sulfonyl group, a carbonyloxy group, a keto group or a single bond. R1 is independently an integer of 0 to 4).

(In the formula, n1 is an integer of 1 to 10.)

^{(Wherein, R A4} each independently, .U1 an aliphatic hydrocarbon group having a hydrogen atom or a C1-5 is an integer from 1 to 8.)

In the general formula ^(a1-2), examples of the aliphatic hydrocarbon group represented by ^{R A1,} for example, a methyl group, an ethyl group, n- propyl group, an isopropyl group, n- butyl group, an isobutyl group, t- butyl group , An alkyl group having 1 to 5 carbon atoms such as an n-pentyl group and the like can be mentioned.
p1 is an integer of 0 to 4, preferably an integer of 0 to 2, more preferably 0 or 1, and even more preferably 0, from the viewpoint of availability. When p1 is an integer of 2 or more, the plurality of ^RA1s may be the same or different.

In the general formula ^(a1-3), examples of the aliphatic hydrocarbon group of 1 to 5 carbon atoms ^{which R A2 represents,} include those similar to the case of ^{R A1.}
Each of q1 is an integer of 0 to 4 independently, and from the viewpoint of availability, each of them is preferably an integer of 0 to 2, more preferably 0 or 2. When q1 is an integer of 2 or more, the plurality of ^RA2s may be the same or different from each other.
As the alkylene group having 1 to 5 carbon atoms which X ^A2 represents, for example, methylene, 1,2-dimethylene group, a 1,3-trimethylene group, 1,4-tetramethylene group, 1,5-pentamethylene group Can be mentioned.
The alkylidene group having 2 to 5 carbon atoms which X ^A2 represents, for example, ethylidene group, propylidene group, isopropylidene group, butylidene group, isobutylidene group, pentylidene group, isopentylidene group, and the like.
Among the above options, the X ^A2 is preferably an alkylene group having 1 to 5 carbon atoms and an alkylidene group having 2 to 5 carbon atoms. More preferable ones are as described above, but a methylene group and an isopropylidene group are more preferable.

In the general formula (a1-3 ^'), the aliphatic hydrocarbon group of 1 to 5 carbon atoms ^{which R A3 represents,} include those similar to the case of ^{R A2.}
Examples of the alkylene group having 1 to 5 carbon atoms and the alkylidene group having 2 to 5 carbon atoms represented by X ^A3 include the same alkylene group having 1 to 5 carbon atoms and the alkylidene group having 2 to 5 carbon atoms represented ^{by X A2.} Be done. As X ^A3 , an alkylidene group having 2 to 5 carbon atoms is preferable, and a propylidene group is more preferable.
r1 is an integer of 0 to 4 independently, and from the viewpoint of availability, each of them is preferably an integer of 0 to 2, more preferably 0 or 1, and even more preferably 0. When r1 is an integer of 2 or more, the plurality of ^RA3s may be the same or different from each other.

As described above, in the general formula ^{(a1-1), X A1} is the formula (a1-2), a group represented by (a1-3), (a1-4) or (a1-5) However, among these, the group represented by the general formula (a1-3) is preferable, and the group represented by the following general formula (a1-3-1) is more preferable.

(In the general formula ^{(a1-3-1), R A2, X} A2 and q1 are the same as those of the general formula (a1-3) can be used, and preferred ones are also the same.)

In the general formula ^(a1-5), examples of the aliphatic hydrocarbon group of 1 to 5 carbon atoms ^{which R A4} represents may be the same as those in the case of the ^{R A1} in general formula (a1-2).

Examples of the component (a1) include fats such as N, N'-ethylene bismaleimide, N, N'-hexamethylene bismaleimide, bis (4-maleimidecyclohexyl) methane, and 1,4-bis (maleimidemethyl) cyclohexane. Group hydrocarbon group-containing maleimide; N, N'-(1,3-phenylene) bismaleimide, N, N'-[1,3- (2-methylphenylene)] bismaleimide, N, N'-[1, 3- (4-Methylphenylene)] bismaleimide, N, N'-(1,4-phenylene) bismaleimide, bis (4-maleimidephenyl) methane, bis (3-methyl-4-maleimidephenyl) methane, 3 , 3'-Dimethyl-5,5'-diethyl-4,4'-diphenylmethane bismaleimide, bis (4-maleimidephenyl) ether, bis (4-maleimidephenyl) sulfone, bis (4-maleimidephenyl) sulfide, bis (4-Maleimide phenyl) ketone, 1,4-bis (4-maleimide phenyl) cyclohexane, 1,4-bis (maleimide methyl) cyclohexane, 1,3-bis (4-maleimide phenoxy) benzene, 1,3-bis (3-Maleimide phenoxy) benzene, bis [4- (3-maleimide phenoxy) phenyl] methane, bis [4- (4-maleimide phenoxy) phenyl] methane, 1,1-bis [4- (3-maleimide phenoxy)) Phenyl] ethane, 1,1-bis [4- (4-maleimide phenoxy) phenyl] ethane, 1,2-bis [4- (3-maleimide phenoxy) phenyl] ethane, 1,2-bis [4- (4) -Maleimide phenoxy) phenyl] ethane, 2,2-bis [4- (3-maleimide phenoxy) phenyl] propane, 2,2-bis [4- (4-maleimide phenoxy) phenyl] propane, 2,2-bis [ 4- (3-Maleimide phenoxy) phenyl] butane, 2,2-bis [4- (4-maleimide phenoxy) phenyl] butane, 2,2-bis [4- (3-maleimide phenoxy) phenyl] -1,1 , 1,3,3,3-hexafluoropropane, 2,2-bis [4- (4-maleimidephenoxy) phenyl] -1,1,1,3,3,3-hexafluoropropane, 4,4- Bis (3-maleimide phenoxy) biphenyl, 4,4-bis (4-maleimide phenoxy) biphenyl, bis [4- (3-maleimide phenoxy) phenyl] ketone, bis [4- (4-ma) Leimidephenoxy) phenyl] ketone, 2,2'-bis (4-maleimidephenyl) disulfide, bis (4-maleimidephenyl) disulfide, bis [4- (3-maleimidephenoxy) phenyl] sulfide, bis [4- (4-( 4-Maleimide phenoxy) phenyl] sulfide, bis [4- (3-maleimide phenoxy) phenyl] sulfoxide, bis [4- (4-maleimide phenoxy) phenyl] sulfoxide, bis [4- (3-maleimide phenoxy) phenyl] sulfone , Bis [4- (4-maleimide phenoxy) phenyl] sulfone, bis [4- (3-maleimide phenoxy) phenyl] ether, bis [4- (4-maleimide phenoxy) phenyl] ether, 1,4-bis [4 -(4-Maleimide phenoxy) -α, α-dimethylbenzyl] benzene, 1,3-bis [4- (4-maleimide phenoxy) -α, α-dimethylbenzyl] benzene, 1,4-bis [4- ( 3-Maleimide phenoxy) -α, α-dimethylbenzyl] benzene, 1,3-bis [4- (3-maleimide phenoxy) -α, α-dimethylbenzyl] benzene, 1,4-bis [4- (4- (4- (4-) Maleimide phenoxy) -3,5-dimethyl-α, α-dimethylbenzyl] benzene, 1,3-bis [4- (4-maleimidephenoxy) -3,5-dimethyl-α, α-dimethylbenzyl] benzene, 1 , 4-bis [4- (3-maleimide phenoxy) -3,5-dimethyl-α, α-dimethylbenzyl] benzene, 1,3-bis [4- (3-maleimide phenoxy) -3,5-dimethyl- Examples thereof include aromatic hydrocarbon group-containing maleimides such as α, α-dimethylbenzyl] benzene and polyphenylmethane maleimide. One of these may be used alone, or two or more thereof may be used in combination.
Among these, from the viewpoint of solubility in a solvent, a maleimide compound having a phenoxy group is preferable, and from the viewpoint of high reactivity and better heat resistance, bis (4-maleimidephenyl) More preferred are methane, 2,2-bis [4- (4-maleimidephenoxy) phenyl] propane.

(Amine compound having at least two primary amino groups (a2))
The amine compound (a2) having at least two primary amino groups (hereinafter, also referred to as “component (a2)”) is preferably an amine compound having two primary amino groups, and the following general formula (a2-1) is preferable. ) Is more preferable.

^{(Wherein, Y A1} is represented by the following general formula (a2-2), a group represented by (a2-3) or (a2-4).)

^{(Wherein, R A5} each independently, .P2 an aliphatic hydrocarbon group having 1 to 5 carbon atoms is an integer of 0-4.)

^{(Wherein, R A6} are each independently, ^{.Y A2} is an aliphatic hydrocarbon group having 1 to 5 carbon atoms, alkylene group of 1 to 5 carbon atoms, an alkylidene group having 2 to 5 carbon atoms, an ether group , A sulfide group, a sulfonyl group, a carbonyloxy group, a keto group, a single bond or a group represented by the following general formula (a2-3'). Q2 is independently an integer of 0 to 4).

^{(Wherein, R A7} each independently, ^{.Y A3} is an aliphatic hydrocarbon group having 1 to 5 carbon atoms, alkylene group of 1 to 5 carbon atoms, an alkylidene group having 2 to 5 carbon atoms, an ether group , A sulfide group, a sulfonyl group, a carbonyloxy group, a keto group or a single bond. S1 is an independently integer of 0 to 4).

^{(Wherein, R A8} each independently represent an alkyl group having 1 to 5 carbon atoms, ^.Z a phenyl group or substituted phenyl group ^A1 are each independently a divalent organic group .m2 is 1 It is an integer of ~ 100.)

In the general formula ^(a2-2), examples of the aliphatic hydrocarbon group represented by ^{R A5,} for example, a methyl group, an ethyl group, n- propyl group, an isopropyl group, n- butyl group, an isobutyl group, t- butyl group , An alkyl group having 1 to 5 carbon atoms such as an n-pentyl group and the like can be mentioned.
p2 is an integer of 0 to 4, and is preferably an integer of 0 to 2 from the viewpoint of availability. When p2 is an integer of 2 or more, the plurality of ^RA5s may be the same or different.

In the general formula ^(a2-3), examples of the aliphatic hydrocarbon group having 1 to 5 ^carbon atoms ^{R A6 represents,} include the same ones as for ^{R A5.}
As the alkylene group having 1 to 5 carbon atoms which Y ^A2 represents, for example, methylene, 1,2-dimethylene group, a 1,3-trimethylene group, 1,4-tetramethylene group, 1,5-pentamethylene group Can be mentioned. The alkylene group is preferably an alkylene group having 1 to 3 carbon atoms, and more preferably a methylene group, from the viewpoints of glass transition temperature, coefficient of thermal expansion, dielectric properties in a high frequency band, solder heat resistance and water-absorbing solder heat resistance. Is.
The alkylidene group having 2 to 5 carbon atoms which Y ^A2 represents, for example, ethylidene group, propylidene group, isopropylidene group, butylidene group, isobutylidene group, pentylidene group, isopentylidene group, and the like. Among these, an isopropylidene group is preferable from the viewpoints of glass transition temperature, coefficient of thermal expansion, dielectric properties in a high frequency band, solder heat resistance and water-absorbing solder heat resistance.
The Y ^A2, among the alternatives, an alkylene group having 1 to 5 carbon atoms, alkylidene group having 2 to 5 carbon atoms preferred. More preferred are as described above.
Each of q2 is an integer of 0 to 4 independently, and from the viewpoint of availability, each of them is preferably an integer of 0 to 2, more preferably 0 or 2. When q2 is an integer of 2 or more, the plurality of ^RA6s may be the same or different from each other.

In the general formula (a2-3 ^'), the aliphatic hydrocarbon group of 1 to 5 carbon atoms ^{which R A7 represents,} include the same ones as for ^{R A6.}
Y ^A3 represents an alkylene group having 1 to 5 carbon atoms, alkylidene group having 2 to 5 carbon ^atoms, alkylene group having 1 to 5 carbon atoms represented by ^{Y A2,} include the same ones as the alkylidene group having 2 to 5 carbon atoms Be done.
The Y ^A3, among the alternatives, preferably an alkylidene group having 2 to 5 carbon atoms, more preferred are as described above.
s1 is an integer of 0 to 4, and from the viewpoint of availability, all of them are preferably an integer of 0 to 2, more preferably 0 or 1, and even more preferably 0. When s1 is an integer of 2 or more, the plurality of ^RA7s may be the same or different from each other.

The general formula (a2-3') is preferably represented by the following general formula (a2-3'-1).

^(Wherein, Y ^{A3, R A7} and s1 is represented by the general formula (the same as a2-3 ') ones, and preferred ones are also the same.)

In the general formula ^(a2-4), examples of the alkyl group having 1 to 5 carbon atoms ^{which R A8} is represented, more preferably an alkyl group having 1 to 3 carbon atoms. The alkyl group R ^A8 represented, for example, a methyl group, an ethyl group, n- propyl group, an isopropyl group, n- butyl group, an isobutyl group, t- butyl group, n- pentyl group and the like, among these , Methyl group is preferred.
^{Examples of the substituent in the substituted phenyl group represented by RA8} include an alkyl group, an alkenyl group, an alkynyl group and the like, and among these, an alkyl group is preferable. Examples of the alkyl group include those similar to the alkyl group represented by ^RA8.
The divalent organic group Z ^A1 represents, for example, an alkylene group, an alkylidene group, an alkenylene group, an alkynylene group, an arylene group, -O-, or they can be cited and a divalent linking group in combination. Among these, an alkylene group, an arylene group, or a divalent linking group in which these are combined is preferable. As the alkylene group, an alkylene group having 1 to 5 carbon atoms is preferable, and an alkylene group having 1 to 3 carbon atoms is more preferable, and examples thereof include a methylene group, an ethylene group, and a propylene group. The arylene group is preferably an arylene group having 6 to 14 ring-forming carbon atoms, and examples thereof include a phenylene group and a naphthylene group.
If ^{Y A1} in the general formula (a2-1) is a group represented by the general formula (a2-4), the component (a2) is a "modified siloxane having a primary amino group at the molecular end" Is called.

Incidentally, in the general formula (a2-1), examples of Y ^A1, a glass transition temperature, thermal expansion coefficient, dielectric properties in a high frequency band, in view of the solder heat resistance and water resistance to soldering heat, the general formula (a2-3 ) Is preferable, and the group represented by the following general formula (a2-3-1) is more preferable.

^(Wherein, Y ^{A2, R A6} and q2 are the same as those of the general formula (a2-3), and preferred ones are also the same.)

^{Y A1} in the general formula (a2-1), the glass transition temperature, thermal expansion coefficient, dielectric properties in a high frequency band, in view of the solder heat resistance and water resistance to soldering heat, the following formula (a2-i) ~ (a2 The group represented by any of −iii) is preferable, and the group represented by the following formula (a2-ii) or (a2-iii) is more preferable.

As the component (a2), a modified siloxane having a primary amino group at the molecular terminal, p-phenylenediamine, m-phenylenediamine, o-phenylenediamine, 3-methyl-1,4-diaminobenzene, 2,5-dimethyl -1,4-diaminobenzene, 4,4'-diaminodiphenylmethane, 3,3'-dimethyl-4,4'-diaminodiphenylmethane, 3,3'-diethyl-4,4'-diaminodiphenylmethane, 4,4' −Diaminodiphenyl ether, 4,4′-diaminodiphenylsulfone, 3,3′-diaminodiphenylsulfone, 4,4′-diaminodiphenylketone, benzene, 3,3′-dimethyl-4,4′-diaminobiphenyl, 2, 2'-dimethyl-4,4'-diaminobiphenyl, 3,3'-dihydroxybenzene, 2,2-bis (3-amino-4-hydroxyphenyl) propane, 3,3'-dimethyl-5,5'- Diethyl-4,4'-diphenylmethanediamine, 2,2-bis (4-aminophenyl) propane, 2,2-bis [4- (4-aminophenoxy) phenyl] propane, 1,3-bis (3-amino) Phenoxy) Benzene, 1,3-bis (4-aminophenoxy) benzene, 1,4-bis (4-aminophenoxy) benzene, 4,4'-bis (4-aminophenoxy) biphenyl, bis [4- (4) -Aminophenoxy) phenyl] sulfone, bis [4- (3-aminophenoxy) phenyl] sulfone, 9,9-bis (4-aminophenyl) fluorene and the like can be mentioned. As the component (a2), one type may be used alone, or two or more types may be used in combination.

Among these, 3,3'-diethyl-4,4'-diaminodiphenylmethane and 2,2'-bis [4- (4-aminophenoxy) phenyl] propane are preferable from the viewpoint of solder heat resistance.
Further, from the viewpoint of low thermal expansion, a modified siloxane having a primary amino group at the molecular terminal is preferable. A commercially available product may be used as the modified siloxane having a primary amino group at the molecular end, and the commercially available product is "X-22-161A" having a primary amino group at both ends (functional group equivalent 800 g / mol). ), "X-22-161B" (functional group equivalent 1,500 g / mol) (above, manufactured by Shin-Etsu Chemical Industry Co., Ltd.), "BY16-853U" (functional group equivalent 460 g / mol) (above, Toray Dow Corning) (Manufactured by Co., Ltd.), "XF42-C5379" (functional group equivalent 750 g / mol) (above, manufactured by Momentive Performance Materials Japan GK) and the like.

Further, the component (a2) preferably contains a modified siloxane having a primary amino group at the molecular end, and is a modified siloxane having a primary amino group at the molecular end, from the viewpoint of achieving both low thermal expansion and solder heat resistance. , It is more preferable to contain an amine compound other than the modified siloxane having a primary amino group at the molecular end, and the modified siloxane having a primary amino group at the molecular end and 3,3'-diethyl-4,4'-. It is more preferable to use in combination with one or more selected from the group consisting of diaminodiphenylmethane and 2,2'-bis [4- (4-aminophenoxy) phenyl] propane.
When a modified siloxane having a primary amino group at the molecular terminal and an amine compound other than the modified siloxane having a primary amino group at the molecular terminal are used in combination as the component (a2), the mass ratio [primary at the molecular terminal]. Amine compounds other than modified siloxanes having an amino group / modified siloxanes having a primary amino group at the molecular terminal] are preferably 3/97 to 90/10, more preferably 10/90 to 80/20, and 15/85 to 15/85. 60/40 is more preferable, and 15/85 to 50/50 is particularly preferable.

The modified maleimide resin (A), which is an addition reaction product of the component (a1) and the component (a2), has, for example, a structural unit represented by the following general formula (A-1).

^{(Wherein, X A1} is the same as ^{X A1} in the general formula ^{(a1-1), Y A1} is the same as ^{Y A1} in the general formula (a2-1).)

((A) Method for producing modified maleimide resin)
The modified maleimide resin (A) can be produced by subjecting the component (a1) and the component (a2) to an addition reaction.
As for the blending amount of the component (a1) and the component (a2) in the addition reaction, the equivalent of the maleimide group of the component (a1) is the equivalent of the primary amino group of the component (a2) from the viewpoint of preventing gelation and heat resistance. The range is preferably more than, and is not particularly limited, but is the ratio of the equivalent of the maleimide group of the component (a1) to the equivalent of the primary amino group of the component (a2) [(a1) component / (a2). ) Component] is preferably 2 to 15, and more preferably 3 to 10.

The reaction temperature in the addition reaction is preferably 70 to 150 ° C., more preferably 100 to 130 ° C. from the viewpoint of productivity and uniform reaction progress. The reaction time is preferably 0.1 to 10 hours, more preferably 1 to 6 hours.

The addition reaction is preferably carried out in an organic solvent. Examples of the organic solvent include alcohol solvents such as ethanol, propanol and propylene glycol monomethyl ether; ketone solvents such as methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone; ester solvents such as acetate ethyl ester; aromatic solvents such as toluene. Examples include nitrogen atom-containing solvents such as dimethylacetamide and N-methylpyrrolidone. As the organic solvent, one type may be used alone, or two or more types may be used in combination.
Among these, cyclohexanone, propylene glycol monomethyl ether, methyl cellosolve, and γ-butyrolactone are preferable from the viewpoint of solubility, and cyclohexanone and propylene glycol monomethyl are preferable from the viewpoint of low toxicity and high volatility and are unlikely to become a residual solvent. Ether is preferred.
From the viewpoint of solubility and reaction rate, the amount of the organic solvent used is preferably 25 to 1,000 parts by mass, preferably 50 to 500 parts by mass, based on 100 parts by mass of the total of the components (a1) and (a2). More preferred.

The content of the (A) modified maleimide resin in the thermosetting resin composition of the present invention is preferably 50 to 95 parts by mass and 60 to 90 parts by mass with respect to 100 parts by mass of the resin component in the thermosetting resin composition. Parts by mass are more preferable, and parts by mass of 65 to 85 are even more preferable.
Here, in the present specification, the "resin component" refers to (A) modified maleimide resin, (B) acrylic elastomer and (C) copolymer resin, and (F) thermoplastic elastomer to be contained as necessary. Is. Further, the “solid content” described later is a non-volatile content excluding volatile substances such as a solvent, and indicates a component that remains without volatilization when the resin composition is dried, and is at room temperature (25). Includes liquid, starch syrup, and wax-like substances (at about ° C).

The content of the (A) modified maleimide resin in the thermosetting resin composition of the present invention is the amount of the (A) modified maleimide resin in the thermosetting resin composition from the viewpoint of elasticity and low thermal expansion. The amount of the component (a1) of the raw material converted from is preferably 30 to 90 parts by mass with respect to 100 parts by mass of the solid content of the resin component in the thermosetting resin composition, and is preferably 50 to 85 parts by mass. Is more preferable.
Further, the content of the (A) modified maleimide resin in the thermosetting resin composition of the present invention is (A) modified in the thermosetting resin composition from the viewpoint of good low thermal expansion and copper foil adhesiveness. The amount of the component (a2) of the raw material converted from the amount of the maleimide resin is preferably 3 to 50 parts by mass with respect to 100 parts by mass of the solid content of the resin component in the thermosetting resin composition. An amount of up to 40 parts by mass is more preferable.

<(B) Acrylic elastomer>
(B) The acrylic elastomer is a polymer containing at least a structural unit derived from an acrylic ester. By blending the component (B) with the thermosetting resin composition of the present invention, the high glass transition temperature, low coefficient of thermal expansion, dielectric properties in the high frequency band, solder heat resistance and water absorption solder heat resistance are excellent. , The cured product has a low elastic modulus. By lowering the elastic modulus of the cured product, the effect of relaxing the stress generated during press molding can be obtained, and the warpage of the substrate is effectively reduced. Further, since the low elasticity has an advantage that the low thermal expansion is promoted, the warp of the substrate is further reduced.
The structural unit derived from the acrylic acid ester means a structural unit formed when the acrylic acid ester monomer is polymerized. (B) The acrylic elastomer does not contain structural units derived from a monomer other than the acrylic acid ester, and may consist of structural units derived from a plurality of different types of acrylic acid esters, or may consist of a plurality of different types. It may contain a structural unit derived from a monomer other than the acrylic acid ester together with a structural unit derived from the acrylic acid ester of.

The acrylic acid ester is not particularly limited, but for example, methyl acrylate, ethyl acrylate, propyl acrylate, isopropyl acrylate, butyl acrylate, isobutyl acrylate, t-butyl acrylate, acrylic acid. Examples thereof include pentyl, hexyl acrylate, cyclohexyl acrylate, octyl acrylate, decyl acrylate, lauryl acrylate, and benzyl acrylate.
Examples of the monomer other than the acrylic acid ester include vinyl-based monomers such as acrylonitrile, acrylamide, acrylic acid, methacrylic acid, methacrylic acid ester, styrene, ethylene, propylene, and butadiene (however, needless to say, acrylic). Acid ester is not included.) (B) The acrylic elastomer may contain structural units derived from two or more different types of monomers other than acrylic acid esters.

(B) The acrylic elastomer may have a reactive functional group, and preferably has a reactive functional group. Examples of the reactive functional group include an epoxy group, a hydroxyl group, a carboxyl group, an amino group, an amide group, an isocyanato group, an acrylic group, a methacryl group, a vinyl group and the like, and at least one selected from the group consisting of these groups. It is preferably a seed. By having these reactive functional groups at at least one of the molecular terminal and the molecular chain, the compatibility with the (A) modified maleimide resin is improved, and it is generated at the time of curing of the thermosetting resin composition of the present invention. The internal stress can be reduced more effectively, and as a result, the warpage of the substrate can be significantly reduced. In particular, an epoxy group, a hydroxyl group, a carboxyl group, an amino group and an amide group are preferable from the viewpoint of adhesion to a metal foil, and an epoxy group, a hydroxyl group and an amide group are more preferable from the viewpoint of heat resistance and insulation reliability. Groups and amide groups are more preferred.

The weight average molecular weight (Mw) of the acrylic elastomer (B) is not particularly limited, but is preferably 10,000 to 2,000,000, more preferably 50,000 to 1,200,000, and 100. 000 to 900,000 is more preferable, and 300,000 to 900,000 is particularly preferable. When the weight average molecular weight (Mw) is at least the lower limit value, low elasticity tends to be maintained, while when it is at least the upper limit value, compatibility and fluidity tend to be good.
In this specification, the weight average molecular weight (Mw) is measured by gel permeation chromatography (GPC) and converted by a calibration curve prepared using standard polystyrene.

The blending amount of the acrylic elastomer (B) is 100 parts by mass in total of the resin components of the thermosetting resin composition from the viewpoint of enhancing the compatibility with the component (A) and lowering the elastic ratio of the cured product. 1 to 50 parts by mass is preferable, 2 to 30 parts by mass is more preferable, 3 to 25 parts by mass is further preferable, 3 to 15 parts by mass may be used, and 15 to 25 parts by mass is used. You may.

<(C) Copolymerized resin>
The (C) copolymer resin is a copolymer resin containing a structural unit derived from an aromatic vinyl compound and a structural unit derived from a carboxylic acid anhydride.
By containing the (C) copolymer resin, the thermosetting resin composition of the present invention has an effect of being particularly excellent in solder heat resistance after water absorption. The reason for this effect is not clear, but it is thought to be as follows.
Conventionally, a method of adding a thermoplastic elastomer to a modified maleimide resin has been used for the purpose of improving the dielectric property. However, since the thermoplastic elastomer has a significantly different skeleton structure from the modified maleimide resin, they are compatible with each other. It was in a difficult state. Therefore, if the modified maleimide resin and the thermoplastic elastomer are simply blended, there is a problem in heat resistance under severe conditions required in recent years (for example, after moisture absorption treatment with a pressure cooker).
The (C) copolymer resin contained in the thermosetting resin composition of the present invention contains a structural unit derived from an aromatic vinyl compound and a structural unit derived from a carboxylic acid anhydride, and is derived from an aromatic vinyl compound. The structural unit is excellent in compatibility with (B) acrylic elastomer, and the structural unit derived from carboxylic acid anhydride is excellent in compatibility with (A) modified maleimide resin. Therefore, the (C) copolymer resin functions as a compatibilizer between the (A) modified maleimide resin and the (B) acrylic elastomer, whereby the (A) modified maleimide resin and the (B) acrylic elastomer can be combined. It is considered that the compatibility was improved and the heat resistance of the solder after water absorption was improved. Furthermore, since the (C) copolymer resin itself also has excellent dielectric properties, it is considered that excellent solder heat resistance could be imparted without impairing the dielectric properties.

As the structural unit derived from the aromatic vinyl compound of the (C) copolymer resin, the structural unit represented by the following general formula (C-1) is preferable. The structural unit derived from the carboxylic acid anhydride of the component (C) is represented by the following general formula (C-2) having a structure similar to that of a maleimide group from the viewpoint of compatibility with the modified maleimide resin (A). The structural unit to be used (that is, the structural unit derived from maleic anhydride) is preferable.

^{(Wherein, R C1} represents a hydrogen atom or an aliphatic hydrocarbon group having 1 to 5 carbon ^{atoms, R C2} each independently an aliphatic hydrocarbon group or a C1-5 carbon 6-20 Indicates an aromatic hydrocarbon group of. X indicates an integer of 0 to 3.)

Examples of the aliphatic hydrocarbon group having 1 to 5 carbon atoms represented by R ^C1 and ^{R C2,} for example, a methyl group, an ethyl group, n- propyl group, an isopropyl group, n- butyl group, an isobutyl group, t- butyl group, Examples thereof include an n-pentyl group. Among these, an aliphatic hydrocarbon group having 1 to 3 carbon atoms is preferable, and a methyl group and an ethyl group are more preferable, from the viewpoint of adhesiveness to the copper foil and dielectric properties in the high frequency band.
The aromatic hydrocarbon group having 6 to 20 carbon atoms R ^C2 represents, for example, a phenyl group, a naphthyl group, an anthryl group, etc. biphenylyl group.
As the structural unit represented by the general formula (C-1), the structural unit represented by the following ^{formula (C-1') in which RC1} is a hydrogen atom and x is 0 is preferable.

(C) Content ratio of the structural unit represented by the general formula (C-1) and the structural unit represented by the general formula (C-2) in the copolymer resin [(C-1) / (C) -2)] (molar ratio) is preferably 2 to 12, more preferably 5 to 10. When the content ratio is 2 or more, the effect of improving the dielectric property and the heat resistance in the high frequency band tends to be sufficient, and when the content ratio is 12 or less, the compatibility tends to be good. Further, when [(C-1) / (C-2)] (molar ratio) is 5 to 10, in addition to having good substrate properties, it is excellent in compatibility with (B) thermoplastic elastomer. Since the content of the structural unit derived from styrene is in a preferable range, the compatibility between the (A) modified maleimide resin and the (B) thermoplastic elastomer is further improved, and the powder removal property of the prepreg is also improved.
The total content of the structural unit represented by the general formula (C-1) and the structural unit represented by the general formula (C-2) in the (C) copolymer resin is preferably 50% by mass or more. 70% by mass or more is more preferable, 90% by mass or more is further preferable, and substantially 100% by mass is particularly preferable.

The copolymerized resin (C) can be produced by copolymerizing an aromatic vinyl compound and a carboxylic acid anhydride.
Examples of the aromatic vinyl compound include styrene, 1-methylstyrene, vinyltoluene and the like. One of these may be used alone, or two or more thereof may be used in combination.
Further, in addition to the aromatic vinyl compound and the carboxylic acid anhydride, various polymerizable components may be copolymerized. Examples of various polymerizable components include vinyl compounds such as ethylene, propylene and butadiene.

As the (C) copolymer resin, a commercially available product can also be used, and as the commercially available product, "SMA (registered trademark) EF30" (styrene / maleic anhydride (molar ratio) = 3, Mw = 9,500), "SMA (registered trademark) EF40" (styrene / maleic anhydride (molar ratio) = 4, Mw = 11,000), "SMA (registered trademark) EF60" (styrene / maleic anhydride (molar ratio) = 6, Mw = 11,500), "SMA (registered trademark) EF80" (styrene / maleic anhydride (molar ratio) = 8, Mw = 14,400) (all manufactured by Sartmer) and the like. Among these, "SMA (registered trademark) EF60" and "SMA-EF80" are preferable.

The content of the (C) copolymer resin in the thermosetting resin composition is preferably 2 to 20 parts by mass and 3 to 15 parts by mass with respect to 100 parts by mass of the resin component in the thermosetting resin composition. More preferably, 6 to 13 parts by mass is further preferable. When the content of the (C) copolymer resin is 2 parts by mass or more, the effect of reducing the dielectric constant is sufficiently obtained, and when it is 20 parts by mass or less, the dispersibility of the (C) copolymer resin is excellent. Excellent heat resistance and peel strength.

<(D) Curing accelerator>
The thermosetting resin composition of the present invention may further contain (D) a curing accelerator from the viewpoint of accelerating the curing reaction.
(D) Examples of the curing accelerator include organic phosphorus compounds such as triphenylphosphine; imidazoles and derivatives thereof; nitrogen-containing compounds such as secondary amines, tertiary amines and quaternary ammonium salts; Dicumyl peroxide, 2,5-dimethyl-2,5-bis (t-butylperoxy) -3-hexine, 2,5-dimethyl-2,5-bis (t-butylperoxy) hexane, α, Organic peroxides such as α'-bis (t-butylperoxy) diisopropylbenzene; organic metal salts such as zinc naphthenate, cobalt naphthenate, tin octylate, cobalt octylate and the like can be mentioned. (D) As the curing accelerator, one type may be used alone, or two or more types may be used in combination.
When the thermosetting resin composition of the present invention contains (D) a curing accelerator, the content thereof is 0.1 to 5 parts by mass with respect to 100 parts by mass of the resin component in the thermosetting resin composition. Is preferable, and 0.3 to 2.0 parts by mass is more preferable.

<(E) Inorganic filler>
The thermosetting resin composition of the present invention may further contain (E) an inorganic filler.
Examples of the inorganic filler (E) include silica, alumina, titanium oxide, mica, barium titanate, strontium titanate, aluminum carbonate, magnesium hydroxide, aluminum hydroxide, silicon carbonate silicon nitride, boron nitride, talc, and carbonic acid. Examples thereof include silicon, quartz powder, and glass such as short glass fiber, fine glass powder, and hollow glass. As the glass, for example, E glass, T glass, D glass and the like are preferably mentioned. (E) As the inorganic filler, one type may be used alone, or two or more types may be used in combination.
Among these, silica is preferable from the viewpoint of dielectric properties, heat resistance and low thermal expansion in the high frequency band. Examples of silica include precipitated silica manufactured by a wet method and having a high water content, and dry silica manufactured by a dry method and containing almost no bound water, etc. Further, the dry silica further depends on the difference in the manufacturing method. , Crushed silica, fumed silica, fused spherical silica and the like. Among these, fused spherical silica is preferable from the viewpoint of low thermal expansion and fluidity when filled in a resin.

The average particle size of the inorganic filler (E) is preferably 0.1 to 10 μm, more preferably 0.3 to 8 μm, further preferably 0.3 to 3 μm, and particularly preferably 0.3 to 1.2 μm. When the average particle size is 0.1 μm or more, the fluidity when the resin is highly filled can be kept good, and when the average particle size is 10 μm or less, the mixing probability of coarse particles is reduced, and defects caused by coarse particles are deteriorated. Occurrence can be suppressed. Here, the average particle size is the particle size of a point corresponding to a volume of 50% when the cumulative frequency distribution curve by the particle size is obtained with the total volume of the particles as 100%, and the laser diffraction scattering method is used. It is a value measured by the particle size distribution measuring device.
The inorganic filler (E) may be surface-treated with a coupling agent. The method of surface treatment with a coupling agent may be a method of surface-treating the (E) inorganic filler before compounding by a dry method or a wet method, and the surface-untreated (E) inorganic filler may be treated with another method. A so-called integral blend treatment method may be used in which a silane coupling agent is added to the composition after blending with the components to obtain a composition.
Examples of the coupling agent include a silane-based coupling agent, a titanate-based coupling agent, a silicone oligomer and the like.

When the thermosetting resin composition of the present invention contains (E) an inorganic filler, the content thereof is preferably 10 to 300 parts by mass with respect to 100 parts by mass of the resin component in the thermosetting resin composition. , 50-250 parts by mass is more preferable. When the content of the inorganic filler (E) is within the above range, the moldability and low thermal expansion property are good.

When the thermosetting resin composition of the present invention contains (E) an inorganic filler, it is treated with a disperser such as a three-roll roll, a bead mill, or a nanomizer, if necessary, to obtain the (E) inorganic filler. It is preferable to improve the dispersibility.

<(F) Thermoplastic Elastomer>
In the thermosetting resin composition of the present invention, (F) a thermoplastic elastomer (however, the component (B) and the component (C) are excluded; hereinafter, also referred to as “component (F)”) may be used. .. The component (F) is not particularly limited and may be appropriately selected from conventionally known thermoplastic elastomers.
Examples of the (F) thermoplastic elastomer include styrene-based thermoplastic elastomers (however, the component (C) is excluded), olefin-based thermoplastic elastomers, urethane-based thermoplastic elastomers, polyester-based thermoplastic elastomers, and polyamide-based heat. Examples thereof include plastic elastomers, silicone-based thermoplastic elastomers, and derivatives thereof. As the component (F), one type may be used alone, or two or more types may be used in combination.

Further, as the (F) thermoplastic elastomer, one having a reactive functional group can be used. Examples of the reactive functional group include an epoxy group, a hydroxyl group, a carboxy group, an amino group, an amide group, an isocyanato group, an acrylic group, a methacryl group and a vinyl group. By having these reactive functional groups at at least one of the molecular terminal and the molecular chain, the compatibility is improved and the heat resistance of the substrate can be improved.
Among these reactive functional groups, it is more preferable to have a carboxy group, an amino group, and a hydroxyl group from the viewpoint of adhesion to the metal foil and from the viewpoint of heat resistance and insulation reliability.

Further, from the viewpoint of (A) compatibility with the modified maleimide resin, (F) the thermoplastic elastomer is preferably a styrene-butadiene copolymer or a styrene-isoprene copolymer, and from the viewpoint of dielectric properties in the high frequency band, these are used. A hydrogenated styrene-based thermoplastic elastomer such as a hydrogenated styrene-butadiene copolymer and a hydrogenated styrene-isoprene copolymer in which the double-bonded portion of the copolymer is hydrogenated is more preferable.
Further, the content of the structural unit derived from styrene in the hydrogenated styrene-based thermoplastic elastomer (hereinafter, also referred to as “styrene amount”) is preferably 20 to 60% by mass, more preferably 25 to 55% by mass, and 25. -40% by mass is more preferable. (F) Moisture absorption by using a hydrogenated styrene-based thermoplastic elastomer such as a hydrogenated styrene-butadiene copolymer and a hydrogenated styrene-isoprene copolymer having a styrene content of 20 to 60% by mass as the thermoplastic elastomer. In addition to improving heat resistance, it is possible to achieve a resin in which the appearance of the prepreg after coating is excellent and the amount of prepreg powder falling off is small. When the amount of styrene is 60% by mass or less, the base material properties (coefficient of thermal expansion, dielectric properties in the high frequency band, heat resistance) are good, and the appearance of the prepreg after coating tends to be less likely to be cracked. .. It is considered that this is due to the fact that the stacking aggregation of styrene is suppressed and the flexibility of the resin is excellent. When the amount of styrene is 20% by mass or more, the substrate properties (coefficient of thermal expansion, dielectric properties in the high frequency band, heat resistance) are good, and in addition, (A) modified maleimide resin and (F) thermoplastic elastomer It has excellent compatibility, the amount of resin powder falling off is small, and it tends to be easy to handle. This is because the maleimide group contained in the (A) modified maleimide resin has a structure similar to that of styrene as compared with butadiene, isoprene, etc., and therefore, (F) when the amount of styrene in the thermoplastic elastomer is 20% by mass or more. (A) It is considered that this is due to the excellent compatibility between the modified maleimide resin and the styrene-based skeleton.

Commercially available products may be used as the styrene-based thermoplastic elastomer, and examples of the commercially available products include "Tough Tech (registered trademark) H1051", "Tough Tech (registered trademark) H1053", "Tough Tech (registered trademark) M1911", and "Tough Tech (registered trademark) M1911". Examples thereof include "Tough Tech (registered trademark) M1913" (all manufactured by Asahi Kasei Chemicals Co., Ltd.), "Septon (registered trademark) 2002", and "Septon (registered trademark) HG252" (manufactured by Kuraray Co., Ltd.).

When the thermosetting resin composition contains (F) a thermoplastic elastomer, the content thereof is preferably 2 to 20 parts by mass with respect to 100 parts by mass of the resin component in the thermosetting resin composition, and 4 to 15 parts by mass. Parts by mass are more preferred. When the content of the (F) thermoplastic elastomer is 2 parts by mass or more, the effect of reducing the dielectric constant can be sufficiently obtained, and when it is 20 parts by mass or less, the (F) thermoplastic elastomer is compatible with each other in the resin. It disperses well and has excellent heat resistance and peel strength.

<Other ingredients>
The modified maleimide resin (A) of the present invention is a thermosetting resin and has good thermosetting properties by itself. However, if necessary, it can be used in combination with other thermosetting resins to provide adhesiveness, mechanical strength, etc. Can be improved.
The thermosetting resin to be used in combination is not particularly limited, and examples thereof include epoxy resin, phenol resin, cyanate resin, isocyanate resin, benzoxazine resin, allyl resin, dicyclopentadiene resin, silicone resin, and triazine resin. May be used alone or in combination of two or more. Among these, cyanate resin and benzoxazine resin are preferable from the viewpoint of moldability and electrical insulation.
Further, although good adhesiveness can be obtained by containing an epoxy resin, the content thereof is preferably 2% by mass or less in the solid content of the thermosetting resin composition. By setting the content of the epoxy resin to 2% by mass or less, the dielectric properties and storage stability in the high frequency band can be improved.

Further, the thermosetting resin composition of the present invention optionally contains a known organic filler, flame retardant, ultraviolet absorber, antioxidant, photopolymerization initiator, fluorescent whitening agent, adhesiveness improver and the like. May be.
Examples of the organic filler include a resin filler composed of at least one selected from polyethylene, polypropylene, polystyrene, polyphenylene ether resin, silicone resin, tetrafluoroethylene resin and the like; and a resin filler having a core-shell structure.
Examples of the flame retardant include aromatic phosphoric acid ester compounds, phosphazene compounds, phosphinic acid esters, metal salts of phosphinic acid compounds, red phosphorus, 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide. Phosphazene flame retardants and their derivatives; nitrogen flame retardants such as guanidine sulfamate, melamine sulfate, melamine polyphosphate, melamine cyanurate; halogen-containing flame retardants containing bromine, chlorine, etc .; inorganic such as antimony trioxide Examples include flame retardants.
Examples of the ultraviolet absorber include benzotriazole-based ultraviolet absorbers and the like.
Examples of the antioxidant include a hindered phenol-based antioxidant, a hindered amine-based antioxidant and the like.
Examples of the photopolymerization initiator include benzophenones, benzyl ketals, thioxanthone-based photopolymerization initiators, and the like.
Examples of the fluorescent whitening agent include a fluorescent whitening agent of a stilbene derivative.
Examples of the adhesiveness improving agent include urea compounds such as ureasilane and the coupling agent.

The thermosetting resin composition of the present invention may be a thermosetting resin composition (so-called varnish) containing an organic solvent for use in the production of prepregs and the like.
Examples of the organic solvent include alcohol solvents such as methanol, ethanol, propanol, butanol, methyl cellosolve, butyl cellosolve and propylene glycol monomethyl ether; ketone solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone; butyl acetate and propylene. Ester-based solvents such as glycol monomethyl ether acetate; Ether-based solvents such as tetrahydrofuran; Aromatic solvents such as toluene, xylene and mesitylene; Nitrogen atom-containing solvents such as dimethylformamide, dimethylacetamide and N-methylpyrrolidone; Examples include a sulfur atom-containing solvent. These organic solvents may be used alone or in combination of two or more.
Among these, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, methyl cellosolve, propylene glycol monomethyl ether, and toluene are preferable from the viewpoint of solubility, and methyl isobutyl ketone, cyclohexanone, propylene glycol monomethyl ether, and toluene are selected from the viewpoint of low toxicity. More preferred.
The solid content concentration of the varnish is preferably 40 to 90% by mass, more preferably 50 to 80% by mass. When the solid content concentration of the varnish is within the above range, the coatability can be kept good and a prepreg having an appropriate amount of the resin composition adhered can be obtained.

[Prepreg]
The prepreg of the present invention is obtained by impregnating a fiber base material with the thermosetting resin composition of the present invention.
The prepreg of the present invention can be produced by impregnating a fiber base material with the thermosetting resin composition of the present invention and semi-curing (B-stage) by heat drying or the like.
As the fiber base material, well-known materials used for various laminated boards for electrical insulating materials can be used. Examples of the material include inorganic fibers such as E glass, S glass, low dielectric glass, and Q glass; organic fibers such as low dielectric glass polyimide, polyester, and tetrafluoroethylene; and mixtures thereof.

These fiber base materials have shapes such as woven fabrics, non-woven fabrics, robinks, chopped strand mats, and surfaced mats, and the materials and shapes are selected according to the intended use, performance, and the like of the molded product. The seeds may be used alone, or two or more materials and two or more shapes may be combined as required. The thickness of the fiber base material is not particularly limited, but for example, a fiber base material of about 0.03 to 0.5 mm can be used. As these fiber base materials, those surface-treated with a silane coupling agent or the like or those subjected to mechanical opening treatment are preferable from the viewpoints of heat resistance, moisture resistance, processability and the like.

The prepreg of the present invention is, for example, a fiber base material so that the amount of the thermosetting resin composition adhered to the fiber base material (the content of the thermosetting resin composition in the prepreg) is 20 to 90% by mass. After impregnating with, it is usually obtained by heating and drying at a temperature of 100 to 200 ° C. for 1 to 30 minutes and semi-curing (B-stage).

[Laminated board]
The laminated board of the present invention is formed by laminating and molding the prepreg of the present invention.
The laminated board of the present invention can be manufactured by preparing one or 2 to 20 prepregs of the present invention and laminating and molding them in a configuration in which metal foils are arranged on one side or both sides thereof. The metal foil is not particularly limited as long as it is used for an electric insulating material, and examples thereof include copper foil, tin foil, tin-lead alloy (solder) foil, nickel foil, and the like, and among these, copper foil is preferable.
For the molding conditions when manufacturing the laminated board, for example, the method of the laminated board for electric insulating material and the multi-layer board can be applied, and a multi-stage press, a multi-stage vacuum press, continuous molding, an autoclave molding machine, etc. It can be molded in the range of ° C., pressure 0.2 to 10 MPa, and heating time 0.1 to 5 hours. Further, the prepreg of the present invention and the wiring board for the inner layer can be combined and laminated to produce a laminated plate.

[Printed wiring board, high-speed communication compatible module]
The printed wiring board of the present invention comprises the prepreg or laminated board of the present invention.
The printed wiring board of the present invention can be manufactured, for example, by forming a circuit on the surface of the laminated board of the present invention. The circuit forming method is not particularly limited, and for example, a known circuit forming method such as a subtractive method or a semi-additive method can be used. Further, a circuit may be formed on the surface of the laminated board of the present invention, and a plurality of the circuit-formed laminated boards may be laminated via the prepreg of the present invention and heat-pressed to form multiple layers. After that, a multi-layer printed wiring board can be manufactured through the formation of through holes or blind via holes by drilling or laser processing and the formation of interlayer wiring by plating or conductive paste. In the present invention, the printed wiring board includes a multilayer printed wiring board.
Further, the present invention also provides a high-speed communication compatible module including the printed wiring board of the present invention. The high-speed communication compatible module of the present invention is particularly suitable for applications such as wireless communication devices and network infrastructure devices that utilize signals in the high frequency range and have a large amount of information communication and high speed.

Next, the present invention will be described in more detail with reference to the following examples, but these examples do not limit the present invention.
The copper-clad laminates obtained in each example were evaluated as follows.

[Evaluation item]
(1) Glass transition temperature (Tg)
A 5 mm square evaluation substrate from which the copper foil was removed was produced by immersing the copper-clad laminates produced in each example in a copper etching solution, and a TMA test device (manufactured by TA Instruments, trade name: Q400) was produced. ) Was used for thermomechanical analysis by the compression method. After the evaluation substrate was mounted on the apparatus in the X direction, the measurement was carried out twice in succession under the measurement conditions of a load of 5 g and a heating rate of 10 ° C./min. The points indicated by the intersections of the different tangents of the thermal expansion curves in the second measurement were obtained and used as the glass transition temperature (Tg).

(2) Coefficient of thermal expansion By immersing the copper-clad laminates produced in each example in a copper etching solution, a 5 mm square evaluation substrate from which the copper foil was removed was produced, and a TMA test device (TA Instruments Co., Ltd.) was produced. A thermomechanical analysis was performed by a compression method using a product, trade name: Q400). After the evaluation substrate was mounted on the apparatus in the X direction, the measurement was carried out twice in succession under the measurement conditions of a load of 5 g and a heating rate of 10 ° C./min. The average coefficient of thermal expansion from 30 ° C. to 100 ° C. in the second measurement was calculated and used as the value of the coefficient of thermal expansion.

(3) Measurement of flexural modulus A 50 mm × 25 mm evaluation substrate from which the copper foil was removed was prepared by immersing the copper-clad laminate prepared in each example in a copper etching solution, and 5 ton tencilon manufactured by Orientec Co., Ltd. Was measured under the conditions of a crosshead speed of 1 mm / min and an interspan distance of 20 mm.

(4) Dielectric characteristics in the high frequency band (relative permittivity and dielectric loss tangent)
A 100 mm × 2 mm evaluation substrate from which the copper foil was removed was prepared by immersing the copper-clad laminate prepared in each example in a copper etching solution, and a cavity resonator device (manufactured by Kanto Electronics Applied Development Co., Ltd.) was used. The relative permittivity and dielectric loss tangent at a frequency of 10 GHz were measured.

(5) Solder heat resistance (solder heat resistance with copper)
An evaluation substrate was prepared by cutting out the copper-clad laminate prepared in each example to a size of 25 mm square, and the evaluation substrate was floated in a solder bath at a temperature of 288 ° C. for a maximum of 60 minutes while observing the appearance. , The time (unit: minutes) until the swelling occurred was measured. The evaluation results are shown in Table 1 as ">60" in which no swelling was confirmed after floating for 60 minutes.

(6) Water-absorbing solder heat resistance (soldering heat resistance with water-absorbing half copper)
The copper-clad laminates produced in each example are cut to a size of 50 mm square, leaving copper on only one surface, and immersing the other surface in a copper etching solution to remove copper on the entire surface to remove half of the 50 mm square. An evaluation substrate with copper was produced. The evaluation substrate with half-copper after being treated in a pressure cooker test (PCT) device (manufactured by Hirayama Seisakusho Co., Ltd.) (condition: 121 ° C., 2.2 atm) for 5 hours is immersed in a solder bath at 288 ° C. for 20 seconds. After that, the heat resistance of the solder with water-absorbing half-copper was evaluated by visually observing the appearance. As for the evaluation result, the one in which no swelling was confirmed was designated as "A", and the one in which swelling was confirmed was designated as "C".

Production Example 1: [Production of Modified Maleimide Resin (A-1)]
In a reaction vessel with a volume of 2 liters that can be heated and cooled with a thermometer, a stirrer and a moisture meter with a reflux condenser, both-terminal diamine-modified siloxane (manufactured by Shinetsu Chemical Industry Co., Ltd., trade name: X-22-161A) ) 15.9 g, 3,3'-diethyl-4,4'-diaminodiphenylmethane 28.6 g, bis (4-maleimidephenyl) methane 280.5 g, and propylene glycol monomethyl ether 200.0 g. The reaction was carried out for 5 hours while refluxing at 126 ° C. to obtain a solution of modified maleimide resin (A-1).

Production Example 2: [Production of modified maleimide resin (A-2)]
Both-terminal diamine-modified siloxane (manufactured by Shin-Etsu Chemical Industry Co., Ltd., trade name: X-22-161B) was placed in a reaction vessel with a volume of 2 liters capable of heating and cooling equipped with a thermometer, a stirrer and a moisture meter with a reflux condenser. ) 14.4 g, 2,2'-bis [4- (4-aminophenoxy) phenyl] propane 56.9 g, bis (4-maleimidephenyl) methane 253.7 g, and propylene glycol monomethyl ether 200.0 g. , And reacted at 126 ° C. for 5 hours to obtain a solution of the modified maleimide resin (A-2).

Production Example 3: [Production of Modified Maleimide Resin (A-3)]
A reaction vessel with a volume of 2 liters that can be heated and cooled with a thermometer, a stirrer and a moisture meter with a reflux condenser, and a diamine-modified siloxane at both ends (manufactured by Shinetsu Chemical Industry Co., Ltd., trade name: X-22-161B ) 15.6 g, 3,3'-diethyl-4,4'-diaminodiphenylmethane 21.8 g, 2,2-bis [4- (4-maleimidephenoxy) phenyl] propane 274.2 g, and propylene glycol monomethyl. 200.0 g of ether was added and reacted at 120 ° C. for 4 hours to obtain a solution of modified maleimide resin (A-3).

Production Example 4: [Production of Modified Maleimide Resin (A-4)]
Both-terminal diamine-modified siloxane (manufactured by Shin-Etsu Chemical Industry Co., Ltd., trade name: X-22-161A) was placed in a reaction vessel with a volume of 2 liters capable of heating and cooling equipped with a thermometer, a stirrer and a moisture meter with a reflux condenser. ) 16.6 g, 2,2'-bis [4- (4-aminophenoxy) phenyl] propane 25.5 g, and 2,2-bis [4- (4-maleimide phenoxy) phenyl] propane 292.6 g. , 200.0 g of propylene glycol monomethyl ether was added, and the mixture was reacted at 126 ° C. for 6 hours to obtain a solution of modified maleimide resin (A-4).

<Examples 1 to 8 and Comparative Examples 1 to 5>
The composition was blended and mixed according to the blending ratio shown in Table 1 (the numerical value in the table is the mass part of the solid content, and in the case of a solution or dispersion, the solid content equivalent amount), and methyl ethyl ketone and toluene were added to the solvent. A varnish having a solid content concentration of 65% by mass was prepared using a mixed solvent.
Next, this varnish was impregnated and coated on an E glass cloth (manufactured by Nitto Boseki Co., Ltd.) having a thickness of 0.1 mm and dried by heating at 160 ° C. for 5 minutes to obtain a prepreg having a resin content of 46% by mass.
Four of these prepregs were stacked, 12 μm electrolytic copper foils were placed one above the other, and pressed at a pressure of 2.5 MPa and a temperature of 200 ° C. for 90 minutes to obtain a copper-clad laminate. Table 1 shows the evaluation results of the obtained copper-clad laminate.

Each component used in the formulation is shown below.

[(A) Modified maleimide resin]
Modified maleimide resin (A-1): Modified maleimide resin (A-1) prepared in Production Example 1.
Modified Maleimide Resin (A-2): Modified Maleimide Resin (A-2) Prepared in Production Example 2
Modified Maleimide Resin (A-3): Modified Maleimide Resin (A-3) Prepared in Production Example 3
Modified Maleimide Resin (A-4): Modified Maleimide Resin (A-4) Prepared in Production Example 4

[(B) Acrylic elastomer]
(B-1) Weight average molecular weight 850,000, epoxy group-containing acrylic polymer [manufactured by Nagase ChemteX Corporation; trade name: SG-P3]
(B-2) Acrylic polymer containing 350,000 weight average molecular weight, epoxy group and amide group [manufactured by Nagase ChemteX Corporation; trade name: SG-80H]

[(C) Copolymer resin containing a structural unit derived from an aromatic vinyl compound and a structural unit derived from a carboxylic acid anhydride]
SMA-EF80: Copolymer of styrene and maleic anhydride (styrene / maleic anhydride (molar ratio) = 8) (manufactured by Sartmer)

[(D) Curing accelerator]
-Curing accelerator 1: tetraphenylphosphonium tetra-p-tolylbolate-Curing accelerator 2: α, α'-bis (t-butylperoxy) diisopropylbenzene-Curing accelerator 3: 2-ethyl-4-methylimidazole Curing Accelerator 4: 2,4-Diamino-6- [2'-Ethyl-4'-Methylimidazolyl- (1')]-Ethyl-s-Triazine

[(E) Inorganic filler]
-Silica: Spherical fused silica surface-treated with phenylaminosilane (average particle size: 0.5 μm)

[(F) Thermoplastic Elastomer]
-Hydrogenated styrene-based thermoplastic elastomer: Septon (registered trademark) 2002 (hydrogenated styrene-isoprene copolymer, styrene content: 30% by mass) (manufactured by Kuraray Co., Ltd.)

As is clear from Table 1, the copper-clad laminates produced in Examples 1 to 8 have a high glass transition temperature, a low coefficient of thermal expansion, a low flexural modulus, and have excellent dielectric properties and solder heat resistance in a high frequency band. Excellent, and also excellent in water absorption solder heat resistance.
On the other hand, in Comparative Example 1 in which the (B) acrylic elastomer and the (C) copolymer resin were not blended, the low thermal expansion property and the dielectric property in the high frequency band were inferior. (C) In Comparative Examples 2 and 3 in which the copolymer resin was not blended, the glass transition temperature was high, the coefficient of thermal expansion was low, the flexural modulus was low, and the dielectric properties in the high frequency band (however, only Comparative Example 2). And the solder heat resistance was good, but the water absorption solder heat resistance was insufficient. In Comparative Examples 4 and 5 in which (B) an acrylic elastomer was not blended, the low thermal expansion property was inferior. In particular, in particular, Comparative Example in which (F) a thermoplastic elastomer was blended instead of (B) not blending an acrylic elastomer. In No. 4, the dielectric property in the high frequency band was good, but in Comparative Example 5 in which (B) the acrylic elastomer was not blended and (F) the thermoplastic elastomer was not blended, the dielectric property in the high frequency band also deteriorated. did.
Further, in Example 4 in which (B) an acrylic elastomer was used, in contrast to Comparative Example 4 in which (B) an acrylic elastomer was not contained but a large amount of styrene-based thermoplastic elastomer was contained. The flexural modulus can be significantly reduced, the flexibility is excellent, the stress generated during press molding is reduced, and low thermal expansion is promoted, so that the warp of the substrate is reduced.

The laminated board obtained by using the thermosetting resin composition of the present invention has low thermal expansion and high glass transition temperature, is excellent in dielectric properties and solder heat resistance in a high frequency band, and is also excellent in water absorption solder heat resistance. Therefore, it is useful for a printed wiring board, particularly a printed wiring board for a module compatible with high-speed communication.

Claims (15)

(A) An addition reaction product of a maleimide compound (a1) having at least two N-substituted maleimide groups and an amine compound (a2) having at least two primary amino groups.
(B) Acrylic elastomer and
(C) A copolymer resin containing a structural unit derived from an aromatic vinyl compound and a structural unit derived from a carboxylic acid anhydride,
A thermosetting resin composition comprising. The thermosetting resin composition according to claim 1, wherein the component (a2) contains a modified siloxane having a primary amino group at the molecular terminal. The thermosetting resin composition according to claim 1 or 2, wherein the component (B) has a reactive functional group. The third aspect of claim 3, wherein the reactive functional group is at least one selected from the group consisting of an epoxy group, a hydroxyl group, a carboxyl group, an amino group, an amide group, an isocyanato group, an acrylic group, a methacryl group and a vinyl group. Thermocurable resin composition. As the component (C), the structural unit derived from the aromatic vinyl compound is the structural unit represented by the following general formula (C-1), and the structural unit derived from the carboxylic acid anhydride is the following general formula (C-2). The thermosetting resin composition according to any one of claims 1 to 4, which contains a copolymer resin which is a structural unit represented by.

^{(Wherein, R C1} represents a hydrogen atom or an aliphatic hydrocarbon group having 1 to 5 carbon ^{atoms, R C2} each independently an aliphatic hydrocarbon group or a C1-5 carbon 6-20 Indicates an aromatic hydrocarbon group of. X indicates an integer of 0 to 3.) Content ratio of the structural unit represented by the general formula (C-1) to the structural unit represented by the general formula (C-2) [(C-1) / (C-2)] (molar ratio) The thermosetting resin composition according to claim 5, wherein the ratio is 5 to 10. The thermosetting according to any one of claims 1 to 6, wherein the content of the component (B) is 1 to 50 parts by mass with respect to 100 parts by mass of the resin component in the thermosetting resin composition. Resin composition. The thermosetting according to any one of claims 1 to 7, wherein the content of the component (C) is 2 to 20 parts by mass with respect to 100 parts by mass of the resin component in the thermosetting resin composition. Resin composition. The thermosetting resin composition according to any one of claims 1 to 8, further comprising (D) a curing accelerator. The thermosetting resin composition according to any one of claims 1 to 9, further comprising (E) an inorganic filler. The thermosetting resin composition according to any one of claims 1 to 10, further comprising (F) a thermoplastic elastomer (however, the component (B) and the component (C) are excluded). Stuff. A prepreg obtained by impregnating a fiber base material with the thermosetting resin composition according to any one of claims 1 to 11. A laminated board obtained by laminating and molding the prepreg according to claim 12. A printed wiring board comprising the prepreg according to claim 12 or the laminated board according to claim 13. A high-speed communication compatible module including the printed wiring board according to claim 14.