JP2022059974A - Method for producing resin composition, resin composition, prepreg, laminate, multilayer printed wiring board, and semiconductor package - Google Patents

Abstract

To provide a method for producing a resin composition having high compatibility, a resin composition produced by the method, and a prepreg, a laminate, a multilayer printed wiring board and a semiconductor package each including the resin composition.SOLUTION: A method for producing a resin composition includes a step of reacting a maleimide compound (A) having at least two N-substituted maleimide groups with a silicone compound (B) having a radical-polymerizable group in an organic solvent through a radical polymerization initiator (C).SELECTED DRAWING: None

Description

The present invention relates to a method for producing a resin composition, a resin composition, a prepreg, a laminated board, a multilayer printed wiring board, and a semiconductor package.

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 the heat resistance of laminated boards for printed wiring boards has been improved to improve reliability. The demand is increasing. In particular, a semiconductor package is required to have both excellent heat resistance and low warpage.

One of the factors that cause the semiconductor package to warp is the difference in the coefficient of thermal expansion between the semiconductor element and the printed wiring board on which the semiconductor element is mounted. In general, the coefficient of thermal expansion of a printed wiring board is larger than the coefficient of thermal expansion of a semiconductor element. Warpage stress is generated. Therefore, as a method of suppressing the warp of the semiconductor package, it is necessary to reduce the coefficient of thermal expansion of the printed wiring board to reduce the difference from the coefficient of thermal expansion of the semiconductor element.

As a method for achieving both heat resistance and low thermal expansion of a printed wiring board, a silicone having at least two amino groups in a single molecular structure in a resin composition containing a maleimide compound having excellent heat resistance as a thermosetting resin. A method for blending a compound has been studied (see, for example, Patent Document 1). According to the technique of Patent Document 1, the coefficient of thermal expansion can be reduced without impairing the heat resistance.

International Publication No. 2012-099134

By the way, in mobile communication devices typified by mobile phones, their base station devices, servers, network infrastructure devices such as routers, large computers, etc., the speed and capacity of signals used are increasing year by year. Along with this, the printed wiring boards mounted on these electronic devices need to support high frequency, and the dielectric characteristics (low dielectric constant and low) in the high frequency band (for example, 10 GHz or more) that enables reduction of transmission loss. There is a demand for a substrate material having excellent dielectric loss tangent; hereinafter sometimes referred to as high frequency characteristics).

Although the resin composition described in Patent Document 1 is excellent in terms of both heat resistance and low thermal expansion, there is room for improvement in terms of the high dielectric properties required in recent years.
As a method for improving the dielectric properties while maintaining heat resistance and low thermal expansion, the polar functional groups contained in the components contained in the resin composition are converted into low polar functional groups as long as they do not significantly affect the curing system. I can think of a way to replace it. However, since the maleimide compound used for ensuring heat resistance has low compatibility with a component having low polarity, it may be separated from the component. For example, when the amino group contained in the silicone compound contained in the resin composition described in Patent Document 1 is replaced with a low-polarity functional group, the silicone compound is separated at the stage of the resin varnish or bleeds out when it is made into a cured product. Problems arise.

In view of such a situation, the present invention relates to a method for producing a resin composition having excellent compatibility, a resin composition obtained by the production method, a prepreg using the resin composition, a laminated board, a multilayer printed wiring board, and the like. The subject is to provide a semiconductor package.

As a result of diligent research to solve the above-mentioned problems, the present inventors have found that the above-mentioned problems can be solved by the following inventions, and have completed the present invention.
That is, the present invention relates to the following [1] to [13].
[1] A maleimide compound (A) having at least two N-substituted maleimide groups and a silicone compound (B) having a radically polymerizable group are reacted in an organic solvent using a radical polymerization initiator (C). A method for producing a resin composition, which comprises a step of subjecting to radical polymerization.
[2] The method for producing a resin composition according to the above [1], wherein the component (B) is a silicone compound having a vinyl group or a (meth) acryloyl group at both ends as the radically polymerizable group.
[3] The method for producing a resin composition according to the above [1] or [2], wherein the functional group equivalent of the component (B) is 300 to 3,000 g / mol.
[4] The method for producing a resin composition according to any one of the above [1] to [3], wherein the component (A) is a bismaleimide compound having an asymmetric structure.
[5] The above [1] to 30 in which the ratio of the amount of the component (A) to the component (B) used [(A) component / (B) component] (molar ratio) to be subjected to the reaction is 1 to 30. The method for producing a resin composition according to any one of [4].
[6] The method for producing a resin composition according to any one of [1] to [5] above, wherein the organic solvent is a mixed solvent of propylene glycol monomethyl ether and toluene.
[7] The method for producing a resin composition according to any one of the above [1] to [6], wherein the reaction temperature of the reaction is 70 to 140 ° C.
[8] The method for producing a resin composition according to any one of the above [1] to [7], wherein the solid content concentration of the reaction solution at the time of the reaction is 5 to 70% by mass.
[9] The resin composition obtained by the method for producing the resin composition according to any one of the above [1] to [8].
[10] A prepreg obtained by impregnating a sheet-shaped fiber reinforced base material with the resin composition according to the above [9].
[11] A laminated board containing the prepreg according to the above [10] and a metal foil.
[12] A multilayer printed wiring board comprising the prepreg according to the above [10] or the laminate according to the above [11].
[13] A semiconductor package in which a semiconductor element is mounted on the multilayer printed wiring board according to the above [12].

According to the present invention, a method for producing a resin composition having excellent compatibility, a resin composition obtained by the production method, a prepreg using the resin composition, a laminated board, a multilayer printed wiring board, and a semiconductor package are provided. Can be done.

In the present specification, the numerical range indicated by using "-" indicates a range including the numerical values before and after "-" as the minimum value and the maximum value, respectively.
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 or the upper limit value of another numerical range.
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 when a plurality of substances corresponding to each component are present in the composition, unless otherwise specified. Means.
The present invention also includes aspects in which the items described in the present specification are arbitrarily combined.

The term "phase" as used herein means that the resins are miscible with each other in nano, micro units, or in appearance, even if they are not necessarily compatible in molecular units, resulting in a transparent solution that is not turbid visually. Means that you are.

[Manufacturing method of resin composition and resin composition]
The method for producing the resin composition of the present embodiment is
Maleimide compound (A) having at least two N-substituted maleimide groups [hereinafter, may be abbreviated as "maleimide compound (A)" or "component (A)". ], And a silicone compound (B) having a radically polymerizable group [hereinafter, may be abbreviated as "silicone compound (B)" or "component (B)". ] May be abbreviated as the radical polymerization initiator (C) [hereinafter, "component (C)". ] Is a method for producing a resin composition, which comprises a step of reacting in an organic solvent.
Further, the resin composition of the present embodiment is a resin composition obtained by the method for producing the resin composition of the present embodiment.
In the following description, the step of reacting in the organic solvent may be referred to as "pre-reaction step", the reaction may be referred to as "pre-reaction", and the solution obtained in the pre-reaction step may be referred to as "resin varnish". be.

<Pre-reaction process>
The pre-reaction step is a step of reacting the component (A) and the component (B) in an organic solvent using the component (C). Hereinafter, each component and various conditions used in the pre-reaction step will be described in detail.

(Maleimide compound (A))
The maleimide compound (A) is a maleimide compound having at least two N-substituted maleimide groups. In the production method of the present embodiment, the obtained resin composition has excellent heat resistance by using the maleimide compound (A).
The maleimide compound (A) may be used alone or in combination of two or more.

The maleimide compound (A) is not particularly limited as long as it is a maleimide compound having two or more N-substituted maleimide groups, but bis (4-maleimidephenyl) methane, polyphenylmethane maleimide, and bis (4-maleimidephenyl) ether. , Bis (4-maleimidephenyl) sulfone, 3,3'-dimethyl-5,5'-diethyl-4,4'-diphenylmethanebismaleimide, 4-methyl-1,3-phenylenebismaleimide, m-phenylenebismaleimide , 2,2-Bis [4- (4-maleimidephenoxy) phenyl] Aromatic maleimide compounds such as propane; 1,6-bismaleimide- (2,2,4-trimethyl) hexane, Binder-type long-chain alkyl pyrophosphate Examples thereof include aliphatic maleimide compounds such as bismaleimide. Among these, aromatic maleimide compounds are preferable, and aromatic bismaleimide compounds are more preferable, and 3,3'-dimethyl-5,5'-diethyl-4,4'are preferable from the viewpoint of adhesiveness to conductors and mechanical properties. -Diphenylmethane bismaleimide is more preferred.

As the maleimide compound (A), a compound represented by the following general formula (A1-1) is preferable.

（式中、Ｘ^ａ１は２価の有機基を示す。）

(In the formula, ^Xa1 represents a divalent organic group.)

Examples of the divalent organic group represented by ^Xa1 in the general formula (A1-1) include the following general formulas (A1-2), (A1-3), (A1-4), (A1-5) or ( Examples thereof include groups represented by A1-6).

（式中、Ｒ^ａ１は、炭素数１～５の脂肪族炭化水素基又はハロゲン原子を示す。ｎ^ａ１は、０～４の整数を示す。＊は結合部位を表す。）

(In the formula, R ^a1 represents an aliphatic hydrocarbon group or a halogen atom having 1 to 5 carbon atoms. n ^a1 represents an integer of 0 to 4. * Represents a bond site.)

Examples of the aliphatic hydrocarbon group having 1 to 5 carbon atoms indicated by ^Ra1 include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a t-butyl group, an n-pentyl group and the like. Can be mentioned. As the aliphatic hydrocarbon group, an aliphatic hydrocarbon group having 1 to 3 carbon atoms is preferable, and a methyl group is more preferable.
n ^a1 represents an integer of 0 to 4, and from the viewpoint of availability, an integer of 0 to 2 is preferable, and 0 is more preferable. When n ^a1 is an integer of 2 or more, a plurality of ^Ra1s may be the same or different from each other.

（式中、Ｒ^ａ２及びＲ^ａ３は、各々独立に、炭素数１～５の脂肪族炭化水素基又はハロゲン原子を示す。Ｘ^ａ２は炭素数１～５のアルキレン基、炭素数２～５のアルキリデン基、エーテル基、スルフィド基、スルホニル基、カルボニルオキシ基、ケト基、単結合、又は下記一般式（Ａ１－３－１）で表される２価の基を示す。ｎ^ａ２及びｎ^ａ３は、各々独立に、０～４の整数を示す。＊は結合部位を表す。）

(In the formula, R ^a2 and R ^a3 independently represent an aliphatic hydrocarbon group or a halogen atom having 1 to 5 carbon atoms. X ^a2 is an alkylene group having 1 to 5 carbon atoms and 2 to 5 carbon atoms. An alkylidene group, an ether group, a sulfide group, a sulfonyl group, a carbonyloxy group, a keto group, a single bond, or a divalent group represented by the following general formula ( ^A1-3-1 ) is shown ^. , Each independently indicates an integer from 0 to 4. * Represents the binding site.)

The description of the aliphatic hydrocarbon group having 1 to 5 carbon atoms represented by R ^a2 and Ra 3 describes the aliphatic hydrocarbon group having ^{1 to 5 carbon atoms represented by R a1 in} the above general formula (A1-2). Same as the description.
Examples of the alkylene group having 1 to 5 carbon atoms indicated by ^Xa2 include a methylene group, a 1,2-dimethylene group, a 1,3-trimethylene group, a 1,4-tetramethylene group, a 1,5-pentamethylene group and the like. Be done. As the alkylene group, an alkylene group having 1 to 3 carbon atoms is preferable, and a methylene group is more preferable.
Examples of the alkylidene group having 2 to 5 carbon atoms indicated by ^Xa2 include an ethylidene group, a propyridene group, an isopropylidene group, a butylidene group, an isobutylidene group, a pentylidene group and an isopentylidene group. As the alkylidene group, an isopropylidene group is preferable.
n ^a2 and n ^a3 indicate an integer of 0 to 4, and from the viewpoint of availability, an integer of 0 to 2 is preferable, and 0 or 2 is more preferable. When n ^a2 or ^{na 3} is an integer of 2 or more, the plurality of R ^a2s or the plurality of R ^a3s may be the same or different from each other.
The divalent group represented by the general formula (A1-3-1) represented by X ^a2 is as follows.

（式中、Ｒ^ａ４及びＲ^ａ５は、各々独立に、炭素数１～５の脂肪族炭化水素基又はハロゲン原子を示す。Ｘ^ａ３は炭素数１～５のアルキレン基、炭素数２～５のアルキリデン基、エーテル基、スルフィド基、スルホニル基、カルボニルオキシ基、ケト基又は単結合を示す。ｎ^ａ４及びｎ^ａ５は、各々独立に、０～４の整数を示す。＊は結合部位を表す。）

(In the formula, R ^a4 and R ^a5 each independently represent an aliphatic hydrocarbon group or a halogen atom having 1 to 5 carbon atoms. X ^a3 is an alkylene group having 1 to 5 carbon atoms and 2 to 5 carbon atoms. It represents an alkylidene group, an ether group, a sulfide group, a sulfonyl group, a carbonyloxy group, a keto group or a single bond. N ^a4 and n ^a5 each independently represent an integer of 0 to 4. * Represents a bond site. )

The description of the aliphatic hydrocarbon group having 1 to 5 carbon atoms represented by R ^a4 and R ^a5 describes the aliphatic hydrocarbon group having 1 to 5 carbon atoms represented by R ^a1 in the above general formula (A1-2). Same as the description.
As the alkylene group having 1 to 5 carbon atoms and the alkylidene group having 2 to 5 carbon atoms represented by X ^a3 , the alkylene group having 1 to 5 carbon atoms and 2 carbon atoms represented by X ^a2 in the above general formula (A1-3). The same as the alkylidene group of ~ 5 can be mentioned.
Among the groups indicated by ^Xa3 , an alkylidene group having 2 to 5 carbon atoms is preferable, and an isopropylidene group is preferable from the viewpoints of high frequency characteristics, adhesiveness to a conductor, heat resistance, glass transition temperature, coefficient of thermal expansion and flame retardancy. More preferred.
n ^a4 and n ^a5 indicate an integer of 0 to 4, and from the viewpoint of availability, an integer of 0 to 2 is preferable, and 0 is more preferable. When n ^a4 or n ^a5 is an integer of 2 or more, the plurality of R ^a4s or the plurality of R ^a5s may be the same or different from each other.

（式中、ｎ^ａ６は、１～１０の整数を示す。＊は結合部位を表す。）

(In the formula, n ^a6 indicates an integer from 1 to 10. * Represents a binding site.)

From the viewpoint of availability, n ^a6 is preferably an integer of 1 to 5, and more preferably an integer of 1 to 3.

（式中、Ｒ^ａ６及びＲ^ａ７は、各々独立に、水素原子又は炭素数１～５の脂肪族炭化水素基を示す。ｎ^ａ７は、１～８の整数を示す。＊は結合部位を表す。）

(In the formula, R ^a6 and R ^a7 each independently represent a hydrogen atom or an aliphatic hydrocarbon group having 1 to 5 carbon atoms. n ^a7 represents an integer of 1 to 8; * represents a binding site. .)

The description of the aliphatic hydrocarbon group having 1 to 5 carbon atoms represented by R ^a6 and R ^a7 is about the aliphatic hydrocarbon group having 1 to 5 carbon atoms represented by R ^a1 in the above general formula (A1-2). Same as the description.
n ^a7 indicates an integer of 1 to 8, preferably an integer of 1 to 3, and more preferably 1.
When n ^a7 is an integer of 2 or more, the plurality of R ^a6s or the plurality of R ^a7s may be the same or different from each other.

（式中、Ｒ^ａ８及びＲ^ａ９は、各々独立に、炭素数１～１０のアルキル基、炭素数１～１０のアルキルオキシ基もしくは炭素数１～１０のアルキルチオ基、炭素数６～１０のアリール基、炭素数６～１０のアリールオキシ基もしくは炭素数６～１０のアリールチオ基、炭素数３～１０のシクロアルキル基、ハロゲン原子、ニトロ基、水酸基又はメルカプト基を示す。ｎ^ａ８及びｎ^ａ９は、各々独立に、０～４の整数を示す。ｎ^ａ８又はｎ^ａ９が２～４の整数の場合、複数のＲ^ａ８同士又は複数のＲ^ａ９同士は、それぞれ同一であっても異なっていてもよい。Ｒ^ａ１０及びＲ^ａ１１は、各々独立に、炭素数１～１０のアルキル基、炭素数１～１０のアルキルオキシ基もしくは炭素数１～１０のアルキルチオ基、炭素数６～１０のアリール基、炭素数６～１０のアリールオキシ基もしくは炭素数６～１０のアリールチオ基、炭素数３～１０のシクロアルキル基、ハロゲン原子、水酸基又はメルカプト基を示す。ｎ^ａ１０及びｎ^ａ１１は、各々独立に、０～３の整数を示す。ｎ^ａ１０又はｎ^ａ１１が２又は３の場合、複数のＲ^ａ１０同士又は複数のＲ^ａ１１同士は、それぞれ同一であっても異なっていてもよい。ｎ^ａ１２は、０．９５～１０．０の数値を示す。＊は結合部位を表す。）

(In the formula, R ^a8 and R ^a9 are independently an alkyl group having 1 to 10 carbon atoms, an alkyloxy group having 1 to 10 carbon atoms or an alkylthio group having 1 to 10 carbon atoms, and an aryl having 6 to 10 carbon atoms. A group, an aryloxy group having 6 to 10 carbon atoms or an ^arylthio group having 6 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a halogen atom, a nitro group, a hydroxyl group or a ^mercapto group. , Each independently indicates an integer of 0 to 4. When n ^a8 or n ^a9 is an integer of 2 to 4, a plurality of R ^a8s or a plurality of R ^a9s may be the same or different from each other. R ^a10 and R ^a11 are independently an alkyl group having 1 to 10 carbon atoms, an alkyloxy group having 1 to 10 carbon atoms or an alkylthio group having 1 to 10 carbon atoms, and an aryl group having 6 to 10 carbon atoms. It represents an aryloxy group having 6 to 10 carbon atoms or an ^arylthio group having 6 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a halogen atom, a hydroxyl group or a ^mercapto group. Indicates an integer from 0 to 3. When n ^a10 or ^na11 is 2 or 3, the plurality of R ^a10s or the plurality of R ^a11s may be the same or different, respectively. N ^a12 is 0. A numerical value from .95 to 10.0 is shown. * Indicates a binding site.)

The ^Xa1 in the general formula (A1-1) is any one of the general formula (A1-3), the general formula (A1-5), or the general formula (A1-6) from the viewpoint of high frequency characteristics. It is preferably a divalent group represented by, more preferably a divalent group represented by any of the following formulas (X a1-1) to (X ^a1 -3), and more preferably the following formula (X ^a1 -1). It is more preferably a divalent group represented by X ^a1-2 ).

（＊は結合部位を表す。）。

(* Represents a binding site.).

Among the maleimide compounds described above, the maleimide compound (A) is preferably a bismaleimide compound having an asymmetric structure. By using the bismaleimide compound having an asymmetric structure, the solubility in an organic solvent is improved, and a resin varnish having further excellent compatibility can be produced.

(Silicone compound (B) having a radically polymerizable group)
Since the silicone compound (B) has a radically polymerizable group having a low polarity while having a silicone skeleton that contributes to low thermal expansion, according to the production method of the present embodiment using the component (B). It is possible to achieve both low thermal expansion and excellent dielectric properties.

Examples of the radically polymerizable group of the silicone compound (B) include a vinyl group, an allyl group, a propargyl group, a butenyl group, an ethynyl group, a phenylethynyl group, a maleimide group, a nadiimide group, and a (meth) acryloyl group. Saturated bond-containing group; epoxy group and the like can be mentioned. The "ethylenically unsaturated bond" means a carbon-carbon double bond capable of an addition reaction, and does not include a double bond of an aromatic ring. Among these, a vinyl group, a (meth) acryloyl group, and an epoxy group are preferable, and a vinyl group and a (meth) acryloyl group are more preferable, from the viewpoint of dielectric properties. The (meth) acryloyl group may be contained in the (meth) acryloyloxy group, in which case the silicone compound (B) has a (meth) acryloyloxy group as a radically polymerizable group. It can be said that it is a thing.
Further, in the present specification, the (meth) acryloyl group means both an acryloyl group and a methacryloyl group, and the (meth) acryloyloxy group means both an acryloyloxy group and a methacryloyloxy group. ..

The number of radically polymerizable groups contained in one molecule of the silicone compound (B) is preferably 1 or more, more preferably 2 to 4, and even more preferably 2 to 3 from the viewpoint of dielectric properties and the coefficient of thermal expansion.
The silicone compound (B) may have a radically polymerizable group at the end or a side chain, but it is preferable to have it at the end from the viewpoint of dielectric properties and reactivity, and both ends are preferable. It is more preferable to have it at both ends, and it is further preferable to have it only at both ends.
From the same viewpoint, the silicone compound (B) is preferably a silicone compound having a vinyl group, a (meth) acryloyl group or an epoxy group at one end or both ends as the radically polymerizable group, and the radically polymerizable group is preferably used. Silicone compounds having vinyl or (meth) acryloyl groups at both ends are more preferred.

The silicone compound (B) preferably contains a structural unit represented by the following general formula (B-1), and more preferably one represented by the following general formula (B-2).

（式中、Ｒ^ｂ１及びＲ^ｂ２は、各々独立に、炭素数１～５のアルキル基、フェニル基又は置換フェニル基を表す。）

(In the formula, R ^b1 and R ^b2 each independently represent an alkyl group, a phenyl group, or a substituted phenyl group having 1 to 5 carbon atoms.)

（式中、Ｒ^ｂ１及びＲ^ｂ２は、上記一般式（Ｂ－１）中のものと同じであり、Ｒ^ｂ３及びＲ^ｂ４は、各々独立に、炭素数１～５のアルキル基、フェニル基又は置換フェニル基を示す。Ｘ^ｂ１及びＸ^ｂ２は、各々独立に、２価の有機基を示し、ｎ^ｂ１は、２～１００の整数を示す。Ｙ^ｂ１及びＹ^ｂ２は、各々独立に、ラジカル重合性基を示す。）

(In the formula, R ^b1 and R ^b2 are the same as those in the above general formula (B-1), and R ^b3 and R ^b4 are each independently an alkyl group having 1 to 5 carbon atoms, a phenyl group or a group. X ^b1 and X ^b2 each independently represent a divalent organic group, n ^b1 represents an integer of 2 to 100; Y ^b1 and Y ^b2 each independently radically polymerize. Indicates a sex group.)

Examples of the alkyl group having 1 to 5 carbon atoms represented by R ^b1 to R ^b4 in the general formulas (B-1) and (B-2) include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, and an n-. Examples thereof include a butyl group, an isobutyl group, a t-butyl group, an n-pentyl group and the like. As the alkyl group, an alkyl group having 1 to 3 carbon atoms is preferable, and a methyl group is more preferable.
Examples of the substituent having the phenyl group in the substituted phenyl group represented by R ^b1 to R ^b4 include an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, an alkynyl group having 2 to 5 carbon atoms and the like. .. Examples of the alkyl group having 1 to 5 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a t-butyl group and an n-pentyl group. Examples of the alkenyl group having 2 to 5 carbon atoms include a vinyl group and an allyl group. Examples of the alkynyl group having 2 to 5 carbon atoms include an ethynyl group and a propargyl group.
Examples of the divalent organic group indicated by X ^b1 and X ^b2 include an alkylene group, an alkenylene group, an alkynylene group, an arylene group, —O— or a divalent linking group in which these are combined. Examples of the alkylene group include an alkylene group having 1 to 10 carbon atoms such as a methylene group, an ethylene group and a propylene group. Examples of the alkenylene group include an alkenylene group having 2 to 10 carbon atoms. Examples of the alkynylene group include an alkynylene group having 2 to 10 carbon atoms. Examples of the arylene group include an arylene group having 6 to 20 carbon atoms such as a phenylene group and a naphthylene group.
Among these, as X ^b1 and X ^b2 , an alkylene group and an arylene group are preferable, and an alkylene group is more preferable.
n ^b1 indicates an integer of 2 to 100, preferably an integer of 2 to 50, more preferably an integer of 3 to 40, and even more preferably an integer of 5 to 30. When n ^b1 is an integer of 2 or more, the plurality of R ^b1s or the plurality of R ^b2s may be the same or different from each other.
The radically polymerizable groups indicated by Y ^b1 and Y ^b2 are as described above.

The functional group equivalent of the silicone compound (B) is not particularly limited, but is preferably 300 to 3,000 g / mol, more preferably 400 to 2,000 g / mol, and 600 to 1 from the viewpoint of dielectric properties and a coefficient of thermal expansion. 000 g / mol is more preferable.

(Radical polymerization initiator (C))
The radical polymerization initiator (C) acts as a polymerization initiator for radical polymerization, and decomposes into an unpaired electron when exposed to energy such as light or heat.
As the component (C), one type may be used alone, or two or more types may be used in combination.

Examples of the radical polymerization initiator (C) include 1,1-di (t-butylperoxy) cyclohexane, 2,2-di (t-butylperoxy) butane, and 2,2-di (4,4-di-). Peroxyketals such as t-butylperoxycyclohexyl) propane, 1,1-di (t-amylperoxy) cyclohexane; hydroperoxides such as cumenehydroperoxide, t-butylhydroperoxide; t-butyl Alkyl peroxides such as peroxyacetate and t-amylperoxyisononanoate; t-butylcumyl peroxide, di-t-butyl peroxide, dicumyl peroxide, di-t-hexyl peroxide, 1,3 -Dialkyl peroxides such as bis (2-t-butylperoxyisopropyl) benzene, 2,5-dimethyl-2,5-bis (t-butylperoxy) hexin-3; t-butylperoxyacetate, t -Peroxyesters such as butylperoxybenzoate and t-butylperoxyisopropyl monocarbonate; peroxycarbonates such as t-butylperoxyisopropylcarbonate and polyethertetrakis (t-butylperoxycarbonate); dibenzoylper Organic peroxides such as diacyl peroxides such as oxides; 2,2'-azobisisobutyronitrile, 2,2'-azobis (2,4-dimethylvaleronitrile), 2,2'-azobis (4) An azo compound such as -methoxy-2'-dimethylvaleronitrile) can be mentioned.

(Organic solvent)
Examples of the organic solvent used in the pre-reaction step include alcohol solvents such as 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; and ethers such as tetrahydrofuran. Solvents; Fragrant solvents such as toluene, xylene, mesitylen; nitrogen atom-containing solvents such as dimethylformamide, dimethylacetamide, N-methylpyrrolidone; sulfur atom-containing solvents such as dimethylsulfoxide; ester solvents such as γ-butyrolactone, etc. Can be mentioned. One type of these organic solvents may be used alone, or two or more types may be used in combination. Among these, propylene glycol monomethyl ether and toluene are preferable, and a mixed solvent of propylene glycol monomethyl ether and toluene is more preferable from the viewpoint of enhancing compatibility.
When a mixed solvent of a mixed solvent of propylene glycol monomethyl ether and toluene is used as the organic solvent, the content ratio of propylene glycol monomethyl ether and toluene [propylene glycol monomethyl ether / toluene] (mass ratio) is not particularly limited, but each From the viewpoint of obtaining a resin varnish having excellent compatibility while suppressing precipitation of components, 50/50 to 98/2 is preferable, 70/30 to 95/5 is more preferable, and 80/20 to 92/8 is preferable. More preferred.

(Amount of each ingredient used)
The ratio of the amount of the component (A) to the component (B) used [(A) component / (B) component] (molar ratio) to be subjected to the pre-reaction of the production method of the present embodiment is not particularly limited, but compatibility. From the viewpoint of heat resistance, dielectric properties and low thermal expansion, 1 to 30 is preferable, 5 to 20 is more preferable, and 8 to 15 is even more preferable.
The mass ratio of the component (A) to the component (B) [(A) component / (B) component] in the pre-reaction of the production method of the present embodiment is not particularly limited, but is compatible, heat resistant, dielectric property and From the viewpoint of low thermal expansion, 1 to 15 is preferable, 1.5 to 10 is more preferable, and 2 to 5 is further preferable.
The amount of the component (C) used in the pre-reaction of the production method of the present embodiment is not particularly limited, but a resin varnish having excellent compatibility while suppressing gelation can be obtained with respect to 100 parts by mass of the component (A). From the viewpoint, 0.01 to 1.0 part by mass is preferable, 0.1 to 0.6 part by mass is more preferable, and 0.2 to 0.4 part by mass is further preferable.
The solid content concentration of the reaction solution in the pre-reaction of the production method of the present embodiment is not particularly limited, but is preferably 5 to 70% by mass, more preferably 15 to 65% by mass, from the viewpoint of compatibility and reaction efficiency. 35-55% by mass is more preferable.

The reaction rate of the pre-reaction of the production method of the present embodiment is not particularly limited, but is preferably 10 to 80%, more preferably 20 to 50%, and further 25 to 35% from the viewpoint of compatibility and moldability. preferable. The reaction rate of the pre-reaction means the ratio of the amount of the reacted raw material component to the total amount of the charged raw material component, and can be obtained by the method described in Examples.

(Reaction temperature and reaction time)
The reaction temperature in the pre-reaction of the production method of the present embodiment is not particularly limited, but is preferably 70 to 140 ° C., preferably 80 to 130 ° C. from the viewpoint of obtaining a resin varnish having excellent compatibility while suppressing gelation. More preferably, 100 to 120 ° C. is even more preferable.
The rate of temperature rise when each component is charged at room temperature and raised to the above reaction temperature is not particularly limited, but is preferably 0.5 to 10 ° C./min, more preferably 1 to 7 ° C./min. 2-5 ° C / min is even more preferred.
The reaction time in the pre-reaction of the production method of the present embodiment is not particularly limited, but is preferably 1 to 16 hours, more preferably 2 to 12 hours from the viewpoint of obtaining a resin varnish having excellent productivity and compatibility. More preferably 5-10 hours.

(Other conditions)
The atmosphere for performing the prereaction of the production method of the present embodiment may be an air atmosphere or an inert atmosphere. Further, if necessary, the organic solvent evaporated during the reaction may be refluxed.
The pre-reaction is preferably carried out while stirring using a known stirring device.

The resin varnish obtained by the pre-reaction has excellent compatibility and is difficult to phase-separate, so that it can be stored as it is at room temperature.
The resin varnish obtained by the above pre-reaction may be used as it is in the production of a prepreg or the like, or may be mixed with other components. In that case, the solid content concentration may be adjusted by adding or distilling off an organic solvent as needed.

<Process of blending other ingredients>
The production method of the present embodiment may further include a step of blending other components with the resin varnish obtained in the pre-reaction step.
Hereinafter, other components that can be used in the process will be described.

(Styrene-based thermoplastic elastomer (D))
In the production method of the present embodiment, the resin composition obtained by blending the styrene-based thermoplastic elastomer (D) has high frequency characteristics, moldability, adhesiveness to a conductor, solder heat resistance, glass transition temperature, and heat. It tends to have an excellent balance between expansion coefficient and flame retardancy.
As the styrene-based thermoplastic elastomer (D), one type may be used alone, or two or more types may be used in combination.

The styrene-based thermoplastic elastomer (D) may have a structural unit other than the structural unit derived from the styrene-based compound in addition to the structural unit derived from the styrene-based compound. The structural unit of the above, the structural unit derived from maleic acid, the structural unit derived from maleic anhydride and the like can be mentioned.
The structural unit derived from butadiene and the structural unit derived from isoprene are preferably hydrogenated. When hydrogenated, the structural unit derived from butadiene is a structural unit in which ethylene units and butylene units are mixed, and the structural unit derived from isoprene is a structural unit in which ethylene units and propylene units are mixed.

Examples of the styrene-based thermoplastic elastomer (D) include a hydrogenated additive of a styrene-butadiene-styrene block copolymer (SBS), a hydrogenated additive of a styrene-isoprene-styrene block copolymer (SIS), and the like. Among these, styrene-butadiene-styrene block copolymer (SBS) hydrogenated additives are preferable from the viewpoints of high frequency characteristics, adhesion to conductors, heat resistance, glass transition temperature and coefficient of thermal expansion.

The hydrogenated styrene-butadiene-styrene block copolymer (SBS) is a styrene-ethylene-butylene-styrene copolymer (SEBS) completely hydrogenated with carbon-carbon double bonds in the butadiene block. , Styrene-butadiene-butylene-styrene (SBBS) formed by partially hydrogenating the carbon-carbon double bond at the 1,2-bonding site in the butadiene block. The complete hydrogenation in SEBS is usually 90% or more, 95% or more, 99% or more, and substantially the total carbon-carbon double bond. It may be 100%. The partial hydrogenation rate in SBBS is, for example, 60 to 85% with respect to the total carbon-carbon double bond.
In SEBS, the content of the structural unit derived from styrene is not particularly limited, but is preferably 5 to 80% by mass from the viewpoint of high frequency characteristics, adhesion to conductors, heat resistance, glass transition temperature and coefficient of thermal expansion. It is more preferably from 70% by mass, still more preferably from 15 to 60% by mass.

When the styrene-based thermoplastic elastomer (D) is blended in the production method of the present embodiment, the blending amount thereof is not particularly limited, but from the viewpoint of high frequency characteristics and heat resistance, the total amount of the resin components is 100 parts by mass. 2 to 60 parts by mass is preferable, 6 to 40 parts by mass is more preferable, and 8 to 30 parts by mass is further preferable.
In the present embodiment, the "resin component" is defined as all components other than inorganic compounds such as inorganic fillers, flame retardants and flame retardant aids among the solid contents constituting the resin composition.
Further, the solid content in the present embodiment means a component in the resin composition other than a volatile substance such as water and a solvent described later. That is, the solid content includes liquid, starch syrup-like or wax-like substances at room temperature around 25 ° C., and does not necessarily mean that the solid content is solid.

(Inorganic filler (E))
In the production method of the present embodiment, the resin composition obtained by blending the inorganic filler (E) tends to have more excellent low thermal expansion property, high elastic modulus, heat resistance and flame retardancy. ..
As the inorganic filler (E), one type may be used alone, or two or more types may be used in combination.

Examples of the inorganic filler (E) include silica, alumina, titanium oxide, mica, verilia, barium titanate, potassium titanate, strontium titanate, calcium titanate, aluminum carbonate, magnesium hydroxide, aluminum hydroxide, and aluminum silicate. , Calcium carbonate, calcium silicate, magnesium silicate, silicon nitride, boron nitride, clay (baked clay, etc.), talc, aluminum borate, silicon carbide and the like. Among these, silica, alumina, mica, and talc are preferable, silica and alumina are more preferable, and silica is further preferable, from the viewpoint of thermal expansion coefficient, elastic modulus, heat resistance, and flame retardancy.
When the inorganic filler (E) is used, it is necessary to improve the dispersibility of the inorganic filler (E) and the adhesion between the inorganic filler (E) and the organic component in the resin composition. , Coupling agent may be used in combination.

The average particle size of the inorganic filler (E) is not particularly limited, but is preferably 0.01 to 20 μm, more preferably 0.1 to 10 μm, and even more preferably 0.2 to 1 μm.
Here, the average particle size in the present embodiment is a particle size at a point corresponding to a volume of 50% when the cumulative frequency distribution curve based on the particle size is obtained with the total volume of particles as 100%. The average particle size can be measured by a particle size distribution measuring device or the like using a laser diffraction / scattering method.

When the inorganic filler (E) is blended in the production method of the present embodiment, the blending amount thereof is not particularly limited, but the total of the resin components is 100 from the viewpoint of the coefficient of thermal expansion, elastic modulus, heat resistance and flame retardancy. With respect to parts by mass, 10 to 250 parts by mass is preferable, 50 to 200 parts by mass is more preferable, and 80 to 180 parts by mass is further preferable.

(Flame retardant (F))
In the production method of the present embodiment, the resin composition obtained by blending the flame retardant (F) tends to have more excellent flame retardancy.
One type of flame retardant (F) may be used alone, or two or more types may be used in combination.

Examples of the flame retardant (F) include an inorganic phosphorus-based flame retardant; an organic phosphorus-based flame retardant; a hydrate of aluminum hydroxide, a metal hydrate such as a hydrate of magnesium hydroxide, and the like. The metal hydroxide may also correspond to an inorganic filler, but if it is a material that can impart flame retardancy, it is classified as a flame retardant.
Examples of the inorganic phosphorus-based flame retardant include red phosphorus; ammonium phosphate such as monoammonium phosphate, diammonium phosphate, triammonium phosphate, and ammonium polyphosphate; and inorganic nitrogen-containing phosphorus compounds such as phosphoric acid amide; phosphorus. Acid; Phosphorus oxide and the like.
Examples of the organic phosphorus-based flame retardant include aromatic phosphoric acid esters, mono-substituted phosphonic acid diesters and di-substituted phosphinic acid esters; metal salts of di-substituted phosphinic acid, organic nitrogen-containing phosphorus compounds, cyclic organic phosphorus compounds and the like. Be done. Among these, aromatic phosphoric acid esters are preferable from the viewpoint of flame retardancy and high frequency characteristics.

As aromatic phosphates, 1,3-phenylenebis (di-2,6-xylenyl phosphate), 4,4'-biphenol-diphenyl phosphate, bisphenol A-diphenyl phosphate, 4,4'-biphenol- Dicresyl phosphate, bisphenol A-dicresyl phosphate, 4,4'-biphenol-di (2,6-xylenyl phosphate), bisphenol A-di (2,6-xylenyl phosphate), 4,4'- Biphenol-polyphenyl phosphate, bisphenol A-polyphenyl phosphate, 4,4'-biphenol-polycresyl phosphate, bisphenol A-polycresyl phosphate, 4,4'-biphenol-poly (2,6-xylenyl phosphate) ), Bisphenol A-poly (2,6-xylenyl phosphate) and the like. Among these, 4,4'-biphenol-di (2,6-xylenyl phosphate) is preferable from the viewpoint of high frequency characteristics, heat resistance, low thermal expansion, adhesion to a conductor, and phase separation state.

As the metal salt of disubstituted phosphinic acid, a metal salt of dialkylphosphinic acid is preferable. Here, examples of the "metal salt" include lithium salt, sodium salt, potassium salt, calcium salt, magnesium salt, aluminum salt, titanium salt, zinc salt and the like. Examples of the alkyl group contained in the dialkylphosphinic acid include an alkyl group having 1 to 10 carbon atoms.

When the flame retardant (F) is blended in the production method of the present embodiment, the blending amount thereof is not particularly limited, but from the viewpoint of flame retardancy, high frequency characteristics, moldability and adhesiveness, the total of the resin components is 100 parts by mass. On the other hand, 3 to 50 parts by mass is preferable, 5 to 45 parts by mass is more preferable, and 10 to 40 parts by mass is further preferable.

(Maleimide compound (A'))
The resin composition obtained by the production method of the present embodiment is a maleimide compound (A') having at least two N-substituted maleimide groups, in addition to the product obtained by the above pre-reaction. ') ”May be called. ] May be contained. The maleimide compound (A') may be the maleimide compound (A) that remains unreacted in the above-mentioned prereaction, or may be separately blended.

(Other optional ingredients)
Further, the production method of the present embodiment further comprises a resin material other than the above-mentioned components, an organic solvent, a coupling agent, an antioxidant, a heat stabilizer, and an antistatic agent, if necessary, as long as the effects of the present invention are not impaired. One or more selected from the group consisting of agents, UV absorbers, pigments, colorants and lubricants [hereinafter, may be abbreviated as "other optional components". ] May be blended. For each of these components, one type may be used alone, or two or more types may be used in combination. Moreover, the production method of this embodiment may not contain these components.
When the above-mentioned other optional components are blended in the production method of the present embodiment, the blending amount of each is not particularly limited, but is, for example, 0.01 parts by mass or more with respect to 100 parts by mass of the total of the resin components. It may be 0.1 part by mass or more, 10 parts by mass or less, 5 parts by mass or less, or 1 part by mass or less.

[Prepreg]
The prepreg of the present embodiment contains the resin composition of the present embodiment and a sheet-shaped fiber reinforced base material.
The prepreg can be formed by using the resin composition of the present embodiment and the sheet-shaped fiber reinforced base material. For example, the resin composition of the present embodiment is impregnated or coated on the sheet-shaped fiber reinforced base material. The resin composition can be produced by heating and drying the resin composition at a temperature of 80 to 200 ° C. for 1 to 30 minutes in a drying furnace to semi-cure the resin composition (B-stage).
The solid content derived from the resin composition in the prepreg of the present embodiment is not particularly limited, but is preferably 30 to 90% by mass, more preferably 35 to 80% by mass, still more preferably 40 to 70% by mass, and 45. ~ 60% by mass is particularly preferable. When the solid content concentration is within the above range, better formability tends to be obtained when the laminated board is formed.

As the sheet-shaped fiber reinforced base material of the prepreg, known ones used for laminated boards for various electric insulating materials are used. Examples of the material of the sheet-shaped fiber reinforcing base material include inorganic fibers such as E glass, D glass, S glass and Q glass; organic fibers such as polyimide, polyester and tetrafluoroethylene; and a mixture thereof. These sheet-shaped fiber reinforced base materials have shapes such as woven fabrics, non-woven fabrics, robinks, chopped strand mats, and surfaced mats. Further, the thickness of the sheet-shaped fiber reinforced base material is not particularly limited, and for example, one having a thickness of 0.02 to 0.5 mm can be used. Further, from the viewpoints of impregnation property of the resin composition, heat resistance when made into a laminated board, hygroscopicity and processability, those surface-treated with a coupling agent or the like, those subjected to mechanically opening treatment, etc. are used. Can be used.

The following hot melt method or solvent method can be adopted as a method for impregnating or coating the sheet-shaped fiber reinforced base material with the resin composition.
The hot melt method is a method in which the resin composition does not contain an organic solvent, and (1) is once coated on coated paper having good peelability from the resin composition and then laminated on a sheet-like fiber reinforced base material. Alternatively, (2) it is a method of directly coating the sheet-shaped fiber reinforced base material with a die coater.
On the other hand, in the solvent method, the resin composition contains an organic solvent, the sheet-shaped fiber reinforced base material is immersed in the obtained resin composition, the resin composition is impregnated into the sheet-shaped fiber reinforced base material, and then the sheet-shaped fiber reinforced base material is impregnated. It is a method of drying.

[Laminate board]
The laminated board of this embodiment is a laminated board containing the prepreg of this embodiment and a metal foil.
In the laminated board of the present embodiment, the metal foil is arranged on one side or both sides of one prepreg of the present embodiment, or the metal foil is arranged on one side or both sides of a stack of two or more prepregs of the present embodiment. Next, a laminated plate can be obtained by heat-press molding. A laminated board having a metal foil is sometimes referred to as a metal-clad laminated board.
The metal of the metal foil is not particularly limited as long as it is used for electrical insulating materials, but from the viewpoint of conductivity, copper, gold, silver, nickel, platinum, molybdenum, ruthenium, aluminum, tungsten, iron, and titanium. , Chromium, or an alloy containing one or more of these metal elements, preferably copper and aluminum, and more preferably copper.
The conditions for heat-press molding are not particularly limited, and for example, the temperature can be 100 to 300 ° C., the pressure can be 0.2 to 10.0 MPa, and the time can be 0.1 to 5 hours. .. Further, for heat pressure molding, a method of maintaining a vacuum state for 0.5 to 5 hours using a vacuum press or the like can be adopted.

[Multilayer printed wiring board]
The multilayer printed wiring board of the present embodiment contains the prepreg of the present embodiment or the laminated board of the present embodiment. The multilayer printed wiring board of the present embodiment uses the prepreg or the laminated plate of the present embodiment, and is subjected to circuit forming processing and multi-layer bonding processing by drilling, metal plating, etching of metal leaf, etc. by a known method. It can be manufactured by doing.

[Semiconductor package]
The semiconductor package of the present embodiment is formed by mounting a semiconductor element on the multilayer printed wiring board of the present embodiment.
In the semiconductor package of the present embodiment, for example, a semiconductor element such as a semiconductor chip or a memory is mounted at a predetermined position on the multilayer printed wiring board of the present embodiment by a known method, and the semiconductor element is sealed with a sealing resin or the like. Can be manufactured by

Although the preferred embodiments of the present invention have been described above, these are examples for explaining the present invention, and the scope of the present invention is not limited to these embodiments. The present invention can be carried out in various embodiments different from the above embodiments without departing from the gist thereof.

Hereinafter, the present invention will be specifically described with reference to examples. However, the present invention is not limited to the following examples.

[Measurement method of reaction rate of pre-reaction]
In each example, the reaction rate of the pre-reaction is the peak area (corresponding to the reaction product) with a retention time of less than 10 minutes when gel permeation chromatography (GPC) is measured using the solution after the reaction as a measurement sample. Using the peak area derived from the component, it was determined as (peak area with a holding time of less than 10 minutes) × 100 / ((peak area with a holding time of less than 10 minutes) + (peak area derived from a raw material component)).
The measurement conditions of GPC are shown below.
Device:
HLP-8320GPC [manufactured by Tosoh Corporation]
Detector: HLC-8320GPC built-in RI detector / UV-8320 [manufactured by Tosoh Corporation]
Column: Guard column; TSKgel guardcollect SuperMP (HZ) -N; TSKgel SuperMultipore HZ-Mx2 (all manufactured by Tosoh Corporation, product name)
Column size: 4.6 x 20 mm (guard column), 7.8 x 300 mm (column)
Eluent: Tetrahydrofuran Sample concentration: 2 mg / 5 mL
Injection volume: 10 μL
Flow rate: 0.35 mL / min Measurement temperature: 35 ° C

[Manufacturing of resin varnish]
Example 1
(Manufacturing of resin varnish A)
In a reaction vessel with a mass of 5 liters that can be heated and cooled with a thermometer, a stirrer, and a water content meter with a reflux cooling tube, as the component (A), 3,3'-dimethyl-5,5'-diethyl-4. , 4'-Diphenylmethane bismaleimide 100 parts by mass, (B) Polydimethylsiloxane having a methacryloyloxy group at both ends (manufactured by Shin-Etsu Chemical Industry Co., Ltd., trade name "X-22-164A", methacryloyloxy group Functional group equivalent 860 g / mol) 39 parts by mass (0.1 mol with respect to 1.0 mol of component (A)), α, α'-di (t-butylperoxy) diisopropylbenzene as component (C) 0.3 parts by mass, 557 parts by mass of a mixed solvent of propylene glycol monomethyl ether and toluene (propylene glycol monomethyl ether / toluene = 90/10 (mass ratio)) was charged (solid content concentration 20% by mass), and the temperature rise rate was 3 ° C. The temperature was raised at / min and reacted at 115 ° C. for 6 hours to obtain a resin varnish A (solid content concentration: 25% by mass). When the reaction rate of the pre-reaction was measured by the above method, it was 32%.
Here, the unreacted component (A) is contained in the resin composition as a maleimide compound (A') as it is.

Examples 2-5
(Manufacturing of resin varnishes B to E)
Resin varnishes B to E were obtained in the same manner as in Example 1 except that various conditions were changed as shown in Table 1.

Comparative Example 1
(Manufacturing of resin varnish F)
Each component was charged into a reaction vessel having a volume of 5 liters capable of heating and cooling equipped with a thermometer, a stirrer, and a water meter with a reflux condenser, having the same composition as in Example 1. Next, the reaction solution was heated at a temperature rising rate of 3 ° C./min, and after confirming that the solid content was dissolved and the phase became uniform at 65 ° C., the reaction solution was cooled to room temperature (25 ° C.) to make a resin varnish. I got F.

[Evaluation of compatibility; time until phase separation]
Each resin varnish was allowed to stand at room temperature (25 ° C.), and the time until separation into two or more phases was measured. The results are shown in Table 1.

＊１：（Ａ）成分１００質量部に対する配合量（質量部）を意味する。

* 1: (A) means the blending amount (parts by mass) with respect to 100 parts by mass of the component.

From Table 1, it can be seen that the resin varnishes A to E of Examples 1 to 5 produced by the production method of the present embodiment have a long time until phase separation and are excellent in compatibility. On the other hand, it can be seen that the resin varnish F of Comparative Example 1 in which the reaction time was 0 hour rapidly undergoes phase separation and is inferior in compatibility.

[Manufacturing of resin plate]
Example 6, Comparative Example 2
Next, using the resin varnish A produced in Example 1 and the resin varnish F produced in Comparative Example 1, a resin plate was produced by the following procedure.
First, each resin varnish was concentrated at 123 ° C. for 1 hour to adjust the solid content concentration to 50% by mass and the reaction rate of the component (A) to 38%.
Next, the resin varnish is applied to a PET film having a thickness of 50 μm (manufactured by Teijin Limited, trade name: G2-50), and then heated and dried at 120 ° C. for 25 minutes to obtain a resin film in a B stage state. Made. After peeling this resin film from the PET film, it was crushed into a resin powder, and the resin powder was put into a Teflon (registered trademark) sheet punched into a size of 1 mm in thickness × 50 mm in length × 30 mm in width. Subsequently, a low profile copper foil (manufactured by Furukawa Electric Co., Ltd., trade name: BF-ANP18) having a thickness of 18 μm was placed above and below it so that the S surface was in contact with the charged resin powder, and the temperature was 230 ° C. The resin composition was cured by heat and pressure molding under the conditions of a pressure of 2.0 MPa and a time of 90 minutes. A resin plate having a thickness of 1 mm was produced by peeling a copper foil from the obtained resin plate with a copper foil.

[Evaluation of compatibility; presence or absence of bleeding]
The presence or absence of bleeding was confirmed by visually observing the surface of the resin plate obtained above. The results are shown in Table 2.

[Evaluation of dielectric properties; measurement of permittivity and dielectric loss tangent]
Using the above resin plate as a measurement sample, the permittivity (Dk) and the dielectric loss tangent (Df) were measured in the 10 GHz band according to the cavity resonator perturbation method. The results are shown in Table 2.

As is clear from the results shown in Table 2, the resin plate obtained in Example 6 produced by using the resin varnish A of the present embodiment did not show bleeding, and had a good dielectric constant and dielectric loss tangent. showed that. On the other hand, the resin plate obtained in Comparative Example 2 produced by using the resin varnish F in which the component (A) and the component (B) were not pre-reacted caused bleeding, and the dielectric property could not be evaluated. rice field.

Since the resin composition of the present invention exhibits excellent dielectric properties in a high frequency band of 10 GHz or higher, prepregs, laminated boards, multilayer printed wiring boards, semiconductor packages, etc. obtained by using the resin composition can be used. Is suitable for electronic component applications that handle high frequency signals.

Claims (13)

A step of reacting a maleimide compound (A) having at least two N-substituted maleimide groups and a silicone compound (B) having a radically polymerizable group in an organic solvent using a radical polymerization initiator (C). A method for producing a resin composition, which comprises. The method for producing a resin composition according to claim 1, wherein the component (B) is a silicone compound having a vinyl group or a (meth) acryloyl group at both ends as the radically polymerizable group. The method for producing a resin composition according to claim 1 or 2, wherein the functional group equivalent of the component (B) is 300 to 3,000 g / mol. The method for producing a resin composition according to any one of claims 1 to 3, wherein the component (A) is a bismaleimide compound having an asymmetric structure. Any of claims 1 to 4, wherein the ratio of the amount of the component (A) to the component (B) used [(A) component / (B) component] (molar ratio) to be subjected to the reaction is 1 to 30. The method for producing a resin composition according to item 1. The method for producing a resin composition according to any one of claims 1 to 5, wherein the organic solvent is a mixed solvent of propylene glycol monomethyl ether and toluene. The method for producing a resin composition according to any one of claims 1 to 6, wherein the reaction temperature of the reaction is 70 to 140 ° C. The method for producing a resin composition according to any one of claims 1 to 7, wherein the solid content concentration of the reaction solution at the time of the reaction is 5 to 70% by mass. A resin composition obtained by the method for producing a resin composition according to any one of claims 1 to 8. A prepreg containing the resin composition according to claim 9 and a sheet-shaped fiber reinforced base material. A laminated board containing the prepreg according to claim 10 and a metal foil. A multilayer printed wiring board comprising the prepreg according to claim 10 or the laminated board according to claim 11. A semiconductor package in which a semiconductor element is mounted on the multilayer printed wiring board according to claim 12.