Resin composition, prepreg, laminate, resin film, printed wiring board, and semiconductor package

Abstract

A resin composition contains (A) one or more substances selected from the group consisting of maleimide resins having one or more N-substituted maleimide groups and derivatives thereof, and (B) compounds having a vinylbenzyl group. The component (B) contains one or more substances selected from the group consisting of (B1) compounds having one or more vinylbenzyl groups directly bonded to a carbon atom and (B2) compounds having three or more vinylbenzyl groups directly bonded to an oxygen atom. The ratio [component (B) / component (A) ] of the component (B) mass reference content to the component (A) mass reference content is 0.11 or more. A prepreg, a laminate, a resin film, a printed wiring board and a semiconductor package using the resin composition are also provided.

Description

Resin compositions, prepregs, laminates, resin films, printed wiring boards, and semiconductor packages

[0001] The present embodiment relates to a resin composition, a prepreg, a laminate, a resin film, a printed wiring board, and a semiconductor package.

[0002] In recent years, electronic devices have become smaller, lighter, and more highly functional, and semiconductor devices mounted on electronic devices have become more highly integrated. Accordingly, printed wiring boards, semiconductor packages, and the like are being required to have higher reliability than ever before. Insulating resin materials used in printed wiring boards, semiconductor packages, and the like are required to have heat resistance and mechanical properties that can withstand the manufacturing and use environments. Therefore, the application of resin compositions using thermosetting resins with excellent heat resistance and mechanical properties has been considered (see, for example, Patent Document 1).

[0003] JP 2009-1783 A

[0004] When forming a substrate for a printed wiring board or the like using a resin composition containing a thermosetting resin, the resin composition is cured by applying heat and pressure to the resin composition. In recent years, in order to realize a recycling-oriented society, there has been a demand for reducing electricity consumption, and there has been a demand for shortening the time for heating and pressurizing the resin composition (hereinafter also referred to as the "heat and pressure treatment time"). However, simply shortening the heat and pressure treatment time of the resin composition results in a problem of a significant decrease in the glass transition temperature of the cured product, possibly due to insufficient curing of the thermosetting resin. Furthermore, since the heat and pressure treatment time applied to the resin composition varies depending on the configuration of the target semiconductor package, it is desirable to achieve a stable glass transition temperature even when the heat and pressure treatment time is changed.

[0005] In view of the current situation, an object of the present embodiment is to provide a resin composition whose glass transition temperature changes little even when the heating and pressurizing treatment time is changed, and a prepreg, a laminate, a resin film, a printed wiring board, and a semiconductor package that use the resin composition.

[0006] The present inventors have conducted extensive research to solve the above-mentioned problems and have found that the problems can be solved by the following embodiments [1] to

[12] . [1] A resin composition comprising: (A) one or more compounds selected from the group consisting of maleimide resins having one or more N-substituted maleimide groups and derivatives thereof; and (B) a compound having a vinylbenzyl group, wherein the component (B) contains one or more compounds selected from the group consisting of (B1) compounds having one or more vinylbenzyl groups directly bonded to a carbon atom and (B2) compounds having three or more vinylbenzyl groups directly bonded to an oxygen atom, and wherein the ratio of the mass-based content of the component (B) to the mass-based content of the component (A) [component (B) / component (A)] is 0.11 or greater. [2] The resin composition according to the above [1], wherein the component (B) contains the component (B1). [3] The resin composition according to [2] above, wherein the component (B1) is a compound containing a fused polycyclic structure containing an aromatic ring and a non-aromatic ring. [4] The resin composition according to [3] above, wherein the fused polycyclic structure containing an aromatic ring and a non-aromatic ring is an indene ring. [5] The resin composition according to any one of [2] to [4] above, wherein the component (B1) is a compound having two or more vinylbenzyl groups directly bonded to carbon atoms. [6] The resin composition according to any one of [1] to [5] above, wherein the component (A) is one or more selected from the group consisting of aromatic maleimide resins having two or more N-substituted maleimide groups and derivatives thereof. [7] A prepreg containing the resin composition according to any one of [1] to [5] above or a semi-cured product of the resin composition. [8] A laminate having a cured product of the resin composition according to any one of [1] to [5] above and a metal foil. [9] A resin film containing the resin composition according to any one of [1] to [5] above or a semi-cured product of the resin composition.

[10] A printed wiring board having a cured product of the resin composition according to any one of [1] to [5] above.

[11] A semiconductor package having the printed wiring board according to

[10] above and a semiconductor element.

[12] A semiconductor package having a semiconductor element and a cured product of the resin composition according to any one of [1] to [5] above that encapsulates the semiconductor element.

[0007] According to the present embodiment, it is possible to provide a resin composition whose glass transition temperature changes little even when the heating and pressurizing treatment time is changed, and a prepreg, a laminate, a resin film, a printed wiring board, and a semiconductor package using the resin composition.

[0008] In this specification, a numerical range indicated using "to" indicates a range that includes the numerical values ​​before and after "to" as the minimum and maximum values, respectively. For example, a numerical range "X to Y" (X and Y are real numbers) means a numerical range that is equal to or greater than X and equal to or less than Y. In this specification, the term "X or greater" means X and a numerical value that exceeds X. In addition, the term "Y or less" in this specification means Y and a numerical value that is less than Y. The lower limit and upper limit of a numerical range described in this specification can be arbitrarily combined with the lower limit or upper limit of another numerical range. In the numerical ranges described in this specification, the lower limit or upper limit of that numerical range may be replaced with a value shown in the examples.

[0009] Unless otherwise specified, each of the components and materials exemplified in this specification may be used alone or in combination of two or more. In this specification, when a resin composition contains a plurality of substances corresponding to each component, the content of each component in the resin composition means the total amount of the plurality of substances present in the resin composition, unless otherwise specified.

[0010] In this specification, the term "solid content" refers to components other than the solvent, and components that are liquid at 25°C are also considered to be solid content.

[0011] The weight average molecular weight (Mw) in this specification refers to a value measured in terms of polystyrene by gel permeation chromatography (GPC). Specifically, the weight average molecular weight (Mw) in this specification can be measured by the method described in the examples.

[0012] In this specification, the term "semi-cured product" is synonymous with a resin composition in a B-stage state according to JIS K 6800 (2006), and the term "cured product" is synonymous with a resin composition in a C-stage state according to JIS K 6800 (2006).

[0013] The mechanism of action described in this specification is speculation and does not limit the mechanism by which the effects of this embodiment are achieved.

[0014] Any combination of the features described in this specification is also included in this embodiment.

[0015] [Resin Composition] The resin composition of the present embodiment contains: (A) one or more compounds selected from the group consisting of maleimide resins having one or more N-substituted maleimide groups and derivatives thereof; and (B) a compound having a vinylbenzyl group, wherein the component (B) contains one or more compounds selected from the group consisting of (B1) compounds having one or more vinylbenzyl groups directly bonded to a carbon atom and (B2) compounds having three or more vinylbenzyl groups directly bonded to an oxygen atom; and the ratio of the content of the component (B) by mass to the content of the component (A) by mass [component (B) / component (A)] is 0.11 or more.

[0016] In this specification, each component may be abbreviated as component (A), component (B), etc., and similar abbreviations may be used for other components.

[0017] <(A) One or More Maleimide Resins Selected from the Group Consisting of Maleimide Resins Having One or More N-Substituted Maleimide Groups and Derivatives Thereof> The resin composition of the present embodiment contains one or more maleimide resins (hereinafter also referred to as "(A) maleimide resin") selected from the group consisting of (A) maleimide resins having one or more N-substituted maleimide groups and derivatives thereof. The (A) maleimide resins may be used alone or in combination of two or more.

[0018] In the following description, a maleimide resin having one or more N-substituted maleimide groups may be referred to as a "maleimide resin (AX)" or "(AX) component." Furthermore, a derivative of a maleimide resin having one or more N-substituted maleimide groups may be referred to as a "maleimide resin derivative (AY)" or "(AY) component."

[0019] (Maleimide Resin (AX)) The maleimide resin (AX) is not particularly limited as long as it is a maleimide resin having one or more N-substituted maleimide groups. From the viewpoints of conductor adhesion and heat resistance, the maleimide resin (AX) is preferably an aromatic maleimide resin having two or more N-substituted maleimide groups, and more preferably an aromatic bismaleimide resin having two N-substituted maleimide groups.

[0020] In this specification, the term "aromatic maleimide resin" refers to a compound having an N-substituted maleimide group directly bonded to an aromatic ring. In addition, in this specification, the term "aromatic bismaleimide resin" refers to a compound having two N-substituted maleimide groups directly bonded to an aromatic ring. In addition, in this specification, the term "aromatic polymaleimide resin" refers to a compound having three or more N-substituted maleimide groups directly bonded to an aromatic ring. In addition, in this specification, the term "aliphatic maleimide resin" refers to a compound having an N-substituted maleimide group directly bonded to an aliphatic hydrocarbon.

[0021] The maleimide resin (AX) is preferably a maleimide resin represented by the following general formula (A-1).

[0022] (In the formula, X Ａ１ is a divalent organic group.

[0023] X in the above general formula (A-1) Ａ１ Examples of the divalent organic group represented by formula (A-3), (A-4), (A-5), or (A-6) below include divalent organic groups represented by formula (A-2), (A-3), (A-4), (A-5), or (A-6) below.

[0024] (In the formula, R Ａ１ is an aliphatic hydrocarbon group having 1 to 5 carbon atoms or a halogen atom.Ａ１ is an integer from 0 to 4. * represents a binding site.)

[0025] R in the above general formula (A-2) Ａ１ Examples of the aliphatic hydrocarbon group having 1 to 5 carbon atoms represented by include alkyl groups having 1 to 5 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, and n-pentyl; alkenyl groups having 2 to 5 carbon atoms; and alkynyl groups having 2 to 5 carbon atoms. The aliphatic hydrocarbon group having 1 to 5 carbon atoms may be either linear or branched. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. n Ａ１ is an integer of 2 or more, a plurality of R Ａ１ They may be the same or different.

[0026] (In the formula, R Ａ２ and R Ａ３ are each independently an aliphatic hydrocarbon group having 1 to 5 carbon atoms or a halogen atom. Ａ２ represents an alkylene group having 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 divalent organic group represented by the following general formula (A-3-1): Ａ２ and n Ａ３ are each independently an integer of 0 to 4. * represents a binding site.

[0027] R in the above general formula (A-3) Ａ２ and R Ａ３ The aliphatic hydrocarbon group having 1 to 5 carbon atoms and the halogen atom represented by R Ａ１ The same as X in the above general formula (A-3) can be mentioned. Ａ２ Examples of the alkylene group having 1 to 5 carbon atoms represented by X include a methylene group, a 1,2-dimethylene group, a 1,3-trimethylene group, a 1,4-tetramethylene group, and a 1,5-pentamethylene group. As the alkylene group having 1 to 5 carbon atoms, a methylene group is preferred. Ａ２Examples of the alkylidene group having 2 to 5 carbon atoms represented by include an ethylidene group, a propylidene group, an isopropylidene group, a butylidene group, an isobutylidene group, a pentylidene group, and an isopentylidene group. Ａ２ and n Ａ３ are each independently an integer of 0 to 4, and from the viewpoint of availability, are preferably all integers of 0 to 2. Ａ２ or n Ａ３ is an integer of 2 or more, a plurality of R Ａ２ R Ａ３ They may be the same or different from each other.

[0028] X in the above general formula (A-3) Ａ２ The divalent organic group represented by formula (A-3-1) is as follows:

[0029] (In the formula, R Ａ４ and R Ａ５ are each independently an aliphatic hydrocarbon group having 1 to 5 carbon atoms or a halogen atom. Ａ３ is an alkylene group having 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. Ａ４ and n Ａ５ are each independently an integer of 0 to 4. * represents a binding site.

[0030] R in the above general formula (A-3-1) Ａ４ and R Ａ５ The aliphatic hydrocarbon group having 1 to 5 carbon atoms and the halogen atom represented by R Ａ１ The same as X in the above general formula (A-3-1) can be mentioned. Ａ３ The alkylene group having 1 to 5 carbon atoms and the alkylidene group having 2 to 5 carbon atoms represented by the above X Ａ２ The same as those in the above general formula (A-3-1) Ａ４ and n Ａ５ are each independently an integer of 0 to 4, and from the viewpoint of availability, are preferably all integers of 0 to 2. Ａ４ or n Ａ５is an integer of 2 or more, a plurality of R Ａ４ R Ａ５ They may be the same or different from each other.

[0031] (In the formula, n Ａ６ is an integer from 0 to 10. * represents a binding site.)

[0032] (In the formula, n Ａ７ is a number from 0 to 5. * represents a binding site.)

[0033] (In the formula, R Ａ６ and R Ａ７ are each independently a hydrogen atom or an aliphatic hydrocarbon group having 1 to 5 carbon atoms. Ａ８ is an integer from 1 to 8. * represents a binding site.)

[0034] R in the above general formula (A-6) Ａ６ and R Ａ７ The aliphatic hydrocarbon group having 1 to 5 carbon atoms and the halogen atom represented by R Ａ１ The same as those in the general formula (A-6) above are included. Ａ８ is an integer of 2 or more, a plurality of R Ａ６ R Ａ７ They may be the same or different from each other.

[0035] Examples of the maleimide resin (AX) include aromatic bismaleimide resins, aromatic polymaleimide resins, and aliphatic maleimide resins. Among these, aromatic bismaleimide resins are preferred. That is, component (A) is preferably at least one selected from the group consisting of aromatic maleimide resins having two or more N-substituted maleimide groups and derivatives thereof. From the viewpoints of heat resistance, dielectric properties, and the like, preferred maleimide resins (AX) include bis(4-maleimidophenyl)methane, m-phenylene bismaleimide, 2,2-bis[4-(4-maleimidophenoxy)phenyl]propane, 4-methyl-1,3-phenylene bismaleimide, 3,3'-dimethyl-5,5'-diethyl-4,4'-diphenylmethane bismaleimide, polyphenylmethane maleimide, aromatic bismaleimide resins having an indane skeleton, and biphenylaralkyl maleimide resins.

[0036] As the maleimide resin derivative (AY), an aminomaleimide resin having a structure derived from the above-mentioned maleimide resin (AX) and a structure derived from a diamine compound is preferred. The aminomaleimide resin can be obtained, for example, by Michael addition of the maleimide resin (AX) and a diamine compound. As the diamine compound, for example, an amine compound having at least two primary amino groups in one molecule as described in JP-A-2020-200406 can be used. Among these, 4,4'-diaminodiphenylmethane, 3,3'-dimethyl-4,4'-diaminodiphenylmethane, 3,3'-diethyl-4,4'-diaminodiphenylmethane, 2,2-bis[4-(4-aminophenoxy)phenyl]propane, 4,4'-[1,3-phenylenebis(1-methylethylidene)]bisaniline, 4,4'-[1,4-phenylenebis(1-methylethylidene)]bisaniline, 3,3'-diethyl-4,4'-diaminodiphenylmethane, and silicone compounds having primary amino groups at both ends are preferred.

[0037] The content of the structure derived from the maleimide resin (AX) in the aminomaleimide resin is preferably 5 to 95 mass%, more preferably 30 to 93 mass%, and even more preferably 70 to 90 mass%. The content of the structure derived from the diamine compound in the aminomaleimide resin is preferably 5 to 95 mass%, more preferably 7 to 70 mass%, and even more preferably 10 to 30 mass%.

[0038] From the viewpoints of heat resistance, moldability, processability, conductor adhesion, and dielectric properties, the content of the maleimide resin (A) in the resin composition of the present embodiment is preferably 1 to 90 mass%, more preferably 20 to 80 mass%, even more preferably 35 to 75 mass%, and particularly preferably 50 to 70 mass%, relative to the total amount (100 mass%) of the resin components in the resin composition of the present embodiment.

[0039] Here, in this specification, the term "resin component" refers to a resin and a compound that forms a resin through a curing reaction. In the resin composition of this embodiment, for example, the components (A), (B), (C), (D), and (F) correspond to the resin components. When the resin composition of this embodiment contains, as optional components, resins or compounds that form a resin through a curing reaction other than the above components, these optional components are also included in the resin component. On the other hand, the component (E) is not included in the resin component.

[0040] The total content of the resin components in the resin composition of this embodiment is preferably 10 to 70 mass%, more preferably 15 to 50 mass%, and even more preferably 20 to 40 mass%, relative to the total solid content (100 mass%) of the resin composition of this embodiment, from the viewpoints of low thermal expansion, heat resistance, flame retardancy, and conductor adhesion.

[0041] <(B) Compound Having a Vinylbenzyl Group> The resin composition of this embodiment contains (B) a compound having a vinylbenzyl group (hereinafter also referred to as "(B) vinylbenzyl compound"). The (B) vinylbenzyl compound contains one or more compounds selected from the group consisting of (B1) compounds having one or more vinylbenzyl groups directly bonded to carbon atoms and (B2) compounds having three or more vinylbenzyl groups directly bonded to oxygen atoms. One (B) vinylbenzyl compound may be used alone, or two or more may be used in combination.

[0042] In the resin composition of this embodiment, the ratio of the mass-based content of component (B) to the mass-based content of component (A) [component (B) / component (A)] (hereinafter also referred to as the "content ratio [component (B) / component (A)]") is 0.11 or greater. When the content ratio [component (B) / component (A)] is 0.11 or greater, the resin composition of this embodiment exhibits a small change in glass transition temperature even when the heating and pressurizing treatment time is changed. Although the reason for this is unclear, it is presumed that the N-substituted maleimide group in the maleimide resin (A) and the vinylbenzyl group in the vinylbenzyl compound (B) react at a relatively low temperature to generate radicals, and that these radicals accelerate the curing reaction of the maleimide resin (A).

[0043] The content ratio [(B) component / (A) component] is preferably 0.12 or more, more preferably 0.13 or more, and even more preferably 0.14 or more, from the viewpoint of minimizing the change in glass transition temperature when the heating and pressurizing treatment time is changed. Furthermore, from the viewpoint of conductor adhesion, the content ratio [(B) component / (A) component] is preferably 50 or less, more preferably 10 or less, even more preferably 1 or less, and particularly preferably 0.3 or less. Furthermore, from the same viewpoints as above, the content ratio [(B) component / (A) component] is preferably 0.11 to 50, more preferably 0.12 to 10, even more preferably 0.13 to 1, and particularly preferably 0.14 to 0.3.

[0044] Preferred embodiments of the vinylbenzyl compound (B) will be described below.

[0045] The vinylbenzyl group contained in the (B) vinylbenzyl compound may be any of an o-vinylbenzyl group, an m-vinylbenzyl group, or a p-vinylbenzyl group, but from the viewpoint of dielectric properties, a p-vinylbenzyl group or an m-vinylbenzyl group is preferred. From the viewpoint of low dielectric dissipation factor, the content of p-vinylbenzyl groups among all vinylbenzyl groups contained in the (B) vinylbenzyl compound is preferably 10 to 100% by mass, more preferably 20 to 90% by mass, even more preferably 30 to 80% by mass, and particularly preferably 40 to 60% by mass. From the viewpoint of low dielectric dissipation factor, the content of m-vinylbenzyl groups among all vinylbenzyl groups contained in the (B) vinylbenzyl compound is preferably 10 to 100% by mass, more preferably 20 to 90% by mass, even more preferably 30 to 80% by mass, and particularly preferably 40 to 60% by mass.

[0046] ((B1) Compound Having One or More Vinylbenzyl Groups Directly Bonded to a Carbon Atom) The component (B1) is not particularly limited as long as it is a compound having one or more vinylbenzyl groups directly bonded to a carbon atom. By including the component (B1) as the vinylbenzyl compound (B), the resin composition of this embodiment tends to be able to reduce the change in glass transition temperature even when the heating and pressurizing treatment time is changed, and also tends to obtain excellent dielectric properties.

[0047] The number of vinylbenzyl groups directly bonded to carbon atoms in one molecule of component (B1) may be one or more; however, component (B1) is preferably a compound having two or more vinylbenzyl groups directly bonded to carbon atoms, more preferably a compound having two to four vinylbenzyl groups directly bonded to carbon atoms, and even more preferably a compound having two or three vinylbenzyl groups directly bonded to carbon atoms.

[0048] The weight average molecular weight (Mw) of the component (B1) is preferably 200 to 800, more preferably 250 to 750, and even more preferably 300 to 700, from the viewpoints of moldability and handleability.

[0049] The vinylbenzyl compound (B) preferably contains a component (B1), and the component (B1) is a compound containing a fused polycyclic structure containing an aromatic ring and a non-aromatic ring. Examples of the fused polycyclic structure containing an aromatic ring and a non-aromatic ring contained in the component (B1) include an indene ring, a fluorene ring, an indane ring, a phenanthrene ring, and an acenaphthylene ring. Among these, an indene ring and a fluorene ring are preferred from the viewpoint of dielectric properties.

[0050] From the viewpoint of dielectric properties, the indene ring-containing component (B1) is preferably a compound represented by the following general formula (B1-1).

[0051] (In the formula, R Ｂ１ are each independently a vinylbenzyl group, and n Ｂ１ is an integer from 1 to 3.

[0052] The compound represented by the general formula (B1-1) may be any of a compound having one vinylbenzyl group, a compound having two vinylbenzyl groups, and a compound having three vinylbenzyl groups, or a mixture thereof. When the compound is a mixture, the average number of vinylbenzyl groups per molecule of the compound represented by the general formula (B1-1) is preferably 1.4 to 2.8, more preferably 1.6 to 2.7, and even more preferably 1.8 to 2.6.

[0053] From the viewpoint of dielectric properties, the component (B1) containing a fluorene ring is preferably a compound represented by the following general formula (B1-2).

[0054] (In the formula, X Ｂ１ is an alkylene group having 1 to 10 carbon atoms, and R Ｂ２ is a hydrogen atom or a vinylbenzyl group.

[0055] X in the above general formula (B1-2) Ｂ１ Examples of the alkylene group having 1 to 10 carbon atoms represented by 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 a 1,6-hexamethylene group.

[0056] (B2) Compound Having Three or More Vinylbenzyl Groups Directly Bonded to Oxygen Atoms) The component (B2) is not particularly limited as long as it is a compound having three or more vinylbenzyl groups directly bonded to oxygen atoms. By including the component (B2) as the vinylbenzyl compound (B), the resin composition of the present embodiment tends to be able to reduce the change in glass transition temperature even when the heating and pressurizing treatment time is changed, and also tends to be able to improve the dielectric properties and curability.

[0057] The vinylbenzyl compound (B) contains a component (B2), and the component (B2) is preferably a compound represented by the following general formula (B2-1) from the viewpoints of curability, moldability, and handleability.

[0058] (In the formula, X Ｂ２ are each independently a divalent hydrocarbon group, and n Ｂ２ is an integer from 1 to 5.

[0059] X in the above general formula (B2-1) Ｂ２ Examples of the divalent hydrocarbon group represented by include alkylene groups having 1 to 5 carbon atoms, alkylidene groups having 2 to 5 carbon atoms, divalent alicyclic hydrocarbon groups having 5 to 12 carbon atoms, arylene groups having 6 to 12 carbon atoms, and divalent groups combining these. Examples of the alkylene groups having 1 to 5 carbon atoms include methylene, 1,2-dimethylene, 1,3-trimethylene, 1,4-tetramethylene, and 1,5-pentamethylene. Examples of the alkylidene groups having 2 to 5 carbon atoms include ethylidene, propylidene, isopropylidene, butylidene, isobutylidene, pentylidene, and isopentylidene groups. Examples of divalent alicyclic hydrocarbon groups having 5 to 12 carbon atoms include divalent groups generated by losing two hydrogen atoms bonded to two different carbon atoms from an alicyclic hydrocarbon compound such as norbornane, decalin, bicycloundecane, saturated dicyclopentadiene, etc. Examples of arylene groups having 6 to 12 carbon atoms include a phenylene group, a naphthylene group, and a biphenylene group.

[0060] X Ｂ２is preferably a group formed by combining an alkylene group having 1 to 5 carbon atoms with an arylene group having 6 to 12 carbon atoms, and more preferably a divalent group represented by the following general formula (B2-2-1):

[0061] (In the formula, X Ｂ３ are each independently an alkylene group having 1 to 5 carbon atoms, and Ar Ｂ１ is an arylene group having 6 to 12 carbon atoms. * represents a bonding site.

[0062] X Ｂ３ The alkylene group having 1 to 5 carbon atoms represented by the above X Ｂ２ Among the above, a methylene group is preferred. Ｂ１ The arylene group having 6 to 12 carbon atoms represented by the above X Ｂ２ Among those mentioned above, a phenylene group and a biphenylene group are preferred. The phenylene group is preferably a 1,4-phenylene group, and the biphenylene group is preferably a 4,4'-biphenylene group.

[0063] n in the above general formula (B2-1) Ｂ２ is an integer of 1 to 50, preferably an integer of 1 to 30, and more preferably an integer of 1 to 20.

[0064] The (B) vinylbenzyl compound may be a commercially available product, or may be synthesized by a known method. Examples of methods for synthesizing the (B) vinylbenzyl compound include reacting a base compound into which a vinylbenzyl group is to be introduced with a styrene having a halogenated methyl group in the presence of a basic compound. Examples of the base compound include compounds having a phenolic hydroxyl group; and compounds having a fused polycyclic structure containing an aromatic ring and a non-aromatic ring, such as fluorene, indene, indane, phenanthrene, and acenaphthylene. Examples of styrenes having a halogenated methyl group include o-chloromethylstyrene, m-chloromethylstyrene, p-chloromethylstyrene, and mixtures thereof. Examples of basic compounds include alkali metal hydroxides and alkali metal alkoxides. A phase transfer catalyst may be used during the reaction. Examples of the phase transfer catalyst include tetrabutylammonium bromide. The reaction is preferably carried out under heating and stirring, and the resulting product may be purified, as necessary, by known methods such as concentration, reprecipitation, and washing.

[0065] From the viewpoint of dielectric properties, the total content of one or more selected from the group consisting of the component (B1) and the component (B2) in the vinylbenzyl compound (B) is preferably 80 to 100 mass%, more preferably 90 to 100 mass%, and even more preferably 95 to 100 mass%, based on the total amount of the vinylbenzyl compound (B).

[0066] The content of the (B) vinylbenzyl compound in the resin composition of this embodiment is preferably 1 to 80 mass%, more preferably 3 to 50 mass%, even more preferably 6 to 35 mass%, and particularly preferably 8 to 20 mass%, relative to the total amount (100 mass%) of the resin components in the resin composition of this embodiment. When the content of the (B) vinylbenzyl compound is equal to or greater than the above-mentioned lower limit, the resin composition of this embodiment tends to exhibit smaller changes in glass transition temperature even when the heating and pressurizing treatment time is changed. Furthermore, when the content of the (B) vinylbenzyl compound is equal to or less than the above-mentioned upper limit, the conductor adhesion tends to be more improved.

[0067] <(C) Epoxy Resin> The resin composition of the present embodiment preferably further contains (C) an epoxy resin. The (C) epoxy resin may be used alone or in combination of two or more.

[0068] Examples of the epoxy resin (C) include bisphenol-type epoxy resins such as bisphenol A-type epoxy resins, bisphenol F-type epoxy resins, and bisphenol S-type epoxy resins; novolac-type epoxy resins such as bisphenol A novolac-type epoxy resins, bisphenol F novolac-type epoxy resins, phenol novolac-type epoxy resins, cresol novolac-type epoxy resins, biphenyl novolac-type epoxy resins, and naphthol novolac-type epoxy resins; aralkyl-type epoxy resins such as phenol aralkyl-type epoxy resins, biphenyl aralkyl-type epoxy resins, and naphthol aralkyl-type epoxy resins; stilbene-type epoxy resins; naphthylene ether-type epoxy resins; biphenyl-type epoxy resins; dihydroanthracene-type epoxy resins; epoxy resins containing a saturated dicyclopentadiene skeleton; cyclohexanedimethanol-type epoxy resins; spiro ring-containing epoxy resins; heterocyclic epoxy resins; alicyclic epoxy resins; aliphatic linear epoxy resins; and rubber-modified epoxy resins. When the resin composition of the present embodiment contains an epoxy resin (C), the content of the epoxy resin (C) is preferably 1 to 25 mass %, more preferably 5 to 20 mass %, and even more preferably 8 to 15 mass %, relative to the total amount (100 mass %) of resin components in the resin composition of the present embodiment, from the viewpoints of heat resistance, moldability, processability, conductor adhesion, and dielectric properties.

[0069] <(D) Phenolic Resin> The resin composition of the present embodiment preferably further contains (D) a phenolic resin. The (D) phenolic resin may be used alone or in combination of two or more.

[0070] Examples of the (D) phenolic resin include novolac-type phenolic resins such as phenol novolac resin and cresol novolac resin; naphthalene-type phenolic resin, high-ortho novolac phenolic resin, terpene-modified phenolic resin, terpene phenol-modified phenolic resin, aralkyl-type phenolic resin, dicyclopentadiene-type phenolic resin, salicylaldehyde-type phenolic resin, benzaldehyde-type phenolic resin, etc. When the resin composition of this embodiment contains the (D) phenolic resin, the content of the (D) phenolic resin is preferably 3 to 30% by mass, more preferably 8 to 25% by mass, and even more preferably 12 to 20% by mass relative to the total amount (100% by mass) of the resin components in the resin composition of this embodiment, from the viewpoints of heat resistance, moldability, processability, conductor adhesion, and dielectric properties.

[0071] <(E) Inorganic Filler> The resin composition of this embodiment preferably further contains an inorganic filler (E). By containing the inorganic filler (E), the resin composition of this embodiment tends to have better low thermal expansion properties and heat resistance. One type of (E) inorganic filler may be used alone, or two or more types may be used in combination.

[0072] (E) inorganic filler can be enumerated as follows: silica, alumina, titanium oxide, mica, beryllia, barium titanate, potassium titanate, strontium titanate, calcium titanate, aluminum carbonate, magnesium hydroxide, aluminum hydroxide, aluminum silicate, calcium carbonate, calcium silicate, magnesium silicate, silicon nitride, boron nitride, clay, talc, aluminum borate, silicon carbide etc.Among these, from the viewpoint of low thermal expansion, heat resistance and flame retardancy, silica, alumina, mica, talc are preferred, silica, alumina are more preferred, and silica is even more preferred.As silica, from the viewpoint of dispersibility and moldability, fused silica is preferred.

[0073] (E) Average particle diameter of inorganic filler (D ５０From the viewpoint of dispersibility of the inorganic filler (E) and fine wiring properties, the average particle diameter (D) of the inorganic filler (E) is preferably 0.1 to 10 μm, more preferably 0.2 to 1 μm, and even more preferably 0.3 to 0.8 μm. ５０ The average particle size of the inorganic filler (E) can be measured, for example, by a particle size distribution analyzer using a laser diffraction scattering method.

[0074] The shape of the (E) inorganic filler may be, for example, spherical or crushed, with spherical being preferred. The (E) inorganic filler may be surface-treated with a surface treatment agent such as a silane coupling agent in order to improve dispersibility and adhesion to organic components.

[0075] When the resin composition of this embodiment contains an inorganic filler (E), the content of the inorganic filler (E) is preferably 20 to 95% by mass, more preferably 40 to 90% by mass, and even more preferably 60 to 80% by mass, based on the total solids content (100% by mass) of the resin composition. When the content of the inorganic filler (E) is equal to or greater than the above-mentioned lower limit, low thermal expansion and heat resistance tend to be more favorable. On the other hand, when the content of the inorganic filler (E) is equal to or less than the above-mentioned upper limit, moldability and conductor adhesion tend to be more favorable.

[0076] <(F) Curing Accelerator> The resin composition of this embodiment preferably further contains a (F) curing accelerator. By containing the (F) curing accelerator, the resin composition of this embodiment tends to have improved curability and better dielectric properties, heat resistance, and conductor adhesion. One type of (F) curing accelerator may be used alone, or two or more types may be used in combination.

[0077] Examples of the (F) curing accelerator include acidic catalysts such as p-toluenesulfonic acid; amine compounds such as triethylamine, tributylamine, pyridine, and dicyandiamide; imidazole compounds such as methylimidazole, phenylimidazole, 2-undecylimidazole, 1-cyanoethyl-2-phenylimidazole, and 1-cyanoethyl-2-phenylimidazolium trimellitate; isocyanate-masked imidazole compounds such as the addition reaction product of hexamethylene diisocyanate resin and 2-ethyl-4-methylimidazole; quaternary ammonium compounds; and phosphorus compounds such as triphenylphosphine and quaternary phosphonium compounds which are addition reaction products of p-benzoquinone and tri-n-butylphosphine. peroxides such as dicumyl peroxide, 2,5-dimethyl-2,5-bis(t-butylperoxy)hexyne-3, 2,5-dimethyl-2,5-bis(t-butylperoxy)hexane, t-butylperoxyisopropyl monocarbonate, and α,α'-bis(t-butylperoxy)diisopropylbenzene; inorganic peroxides such as potassium persulfate, sodium persulfate, and ammonium persulfate; azo compounds such as 2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), and 2,2'-azobis(4-methoxy-2'-dimethylvaleronitrile); carboxylates of manganese, cobalt, zinc, and the like; and acidic catalysts such as p-toluenesulfonic acid. Among these, isocyanate-masked imidazole compounds are preferred from the viewpoints of curing acceleration effect and storage stability.

[0078] When the resin composition of this embodiment contains a (F) curing accelerator, the content of the (F) curing accelerator is preferably 0.01 to 10 parts by mass, more preferably 0.1 to 7 parts by mass, and even more preferably 0.2 to 5 parts by mass, per 100 parts by mass of the (A) thermosetting resin. When the content of the (F) curing accelerator is equal to or greater than the above-mentioned lower limit, a sufficient curing acceleration effect tends to be easily obtained. Furthermore, when the content of the (F) curing accelerator is equal to or less than the above-mentioned upper limit, storage stability tends to be more easily improved.

[0079] <Other Optional Components> The resin composition of the present embodiment may further contain other optional components, such as resin materials other than the above components, flame retardants, antioxidants, heat stabilizers, antistatic agents, UV absorbers, pigments, colorants, lubricants, silane coupling agents, organic solvents, and other additives, as needed. Each of the other optional components may be used alone, or two or more may be used in combination. The content of the above optional components in the resin composition of the present embodiment is not particularly limited, and they may be used as needed within a range that does not impair the effects of the present embodiment. Furthermore, the resin composition of the present embodiment may not contain the above optional components, depending on the desired performance.

[0080] The resin composition of this embodiment may contain an organic solvent from the viewpoint of handleability. Examples of organic solvents include alcohol-based solvents such as ethanol, propanol, butanol, methyl cellosolve, butyl cellosolve, and propylene glycol monomethyl ether; ketone-based solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone; ether-based solvents such as tetrahydrofuran; aromatic hydrocarbon-based solvents such as toluene, xylene, and mesitylene; nitrogen-containing solvents such as dimethylformamide, dimethylacetamide, and N-methylpyrrolidone; sulfur-containing solvents such as dimethyl sulfoxide; and ester-based solvents such as γ-butyrolactone. Among these, from the viewpoint of solubility, alcohol-based solvents, ketone-based solvents, nitrogen-containing solvents, and aromatic hydrocarbon-based solvents are preferred, ketone-based solvents are more preferred, and methyl ethyl ketone is even more preferred.

[0081] <Method for producing resin composition> The resin composition of this embodiment can be produced by mixing the components by a known method. At this time, the components may be dissolved or dispersed while stirring. The conditions such as the mixing order, temperature, and time are not particularly limited and may be set as desired depending on the types of raw materials, etc.

[0082] <Physical Properties of Resin Composition> (Rate of Change in Glass Transition Temperature with Heat and Pressure Treatment Time) In the resin composition of this embodiment, the rate of change in glass transition temperature with heat and pressure treatment time, measured under the following conditions, is preferably −20% to +20%, more preferably −15% to +15%, even more preferably −12% to +12%, still more preferably −10% to +10%, still more preferably −8% to +8%, still more preferably −7% to +7%, still more preferably −6% to +6%, and particularly preferably −5% to +5%. <Method for Measuring Rate of Change in Glass Transition Temperature with Heat and Pressure Treatment Time> A resin composition and a glass cloth (glass type: T-glass, basis weight: 114 g / m) were mixed. ２ Seven 0.1 mm thick prepregs containing a glass cloth thickness of 0.098 mm were stacked and subjected to a heating and pressurizing treatment at a temperature of 240°C and a pressure of 3.0 MPa for 100 minutes or 40 minutes, to obtain a laminate (100) produced with a heating and pressurizing treatment time of 100 minutes, and a laminate (40) produced with a heating and pressurizing treatment time of 40 minutes. The obtained laminate (40) and laminate (100) were cut into 4 mm x 30 mm pieces in the plane direction and dried at 105°C for 1 hour to obtain test specimens. Using the test specimens as the measurement subject, dynamic viscoelasticity measurements were performed using a dynamic viscoelasticity measuring device under conditions of a heating rate of 5°C / min, a frequency of 10 Hz, and a measurement temperature range of 40 to 400°C. The temperature at which tanδ reaches a maximum value in the obtained temperature-loss tangent (tanδ) curve was taken as the glass transition temperature (Tg). The glass transition temperature change rate with heating and pressure treatment time is calculated from the glass transition temperature Tg(100) of the laminate (100) and the glass transition temperature Tg(40) of the laminate (40) by the following formula (1): Glass transition temperature change rate with heating and pressure treatment time (%) = [Tg(100) - Tg(40)] x 100 / Tg(100) (1) A more detailed method for measuring the glass transition temperature change rate with heating and pressure treatment time is as described in the Examples. Note that "T glass" in this embodiment refers to SiO ２ (64-66% by mass), Al ２ O ３ (24 to 26 mass %), MgO (9 to 11 mass %).

[0083] <Glass Transition Temperature of Laminate (40)> When the resin composition of this embodiment is formed into the laminate (40) of the above-mentioned "Method for Measuring the Rate of Change in Glass Transition Temperature with Heat and Pressure Treatment Time", the glass transition temperature Tg(40) of the laminate (40) is preferably 200 to 400°C, more preferably 240 to 370°C, even more preferably 255 to 360°C, and particularly preferably 260 to 350°C, from the viewpoints of heat resistance and ease of production.

[0084] <Thermal expansion coefficient of laminate (40)> When the resin composition of this embodiment is formed into the laminate (40) of the above-mentioned "Method for measuring the rate of change in glass transition temperature with heating and pressure treatment time", the thermal expansion coefficient of the laminate (40) is preferably 4.5 to 25.0 ppm / °C, more preferably 5.0 to 20.0 ppm / °C, even more preferably 5.5 to 13.0 ppm / °C, and particularly preferably 6.0 to 11.0 ppm / °C, from the viewpoint of low thermal expansion and ease of production. The thermal expansion coefficient of the laminate (40) can be measured by the method described in the examples.

[0085] <Bending Modulus of Laminate (40)> When the resin composition of this embodiment is formed into the laminate (40) of the above-mentioned "Method for Measuring the Rate of Change in Glass Transition Temperature with Heat and Pressure Treatment Time", the bending modulus of the laminate (40) is preferably 25 to 50 GPa, more preferably 30 to 45 GPa, even more preferably 33 to 42 GPa, and particularly preferably 34 to 40 GPa, from the viewpoints of mechanical strength and ease of manufacture. The bending modulus of the laminate (40) can be measured by the method described in the examples.

[0086] [Prepreg] The prepreg of the present embodiment is a prepreg containing the resin composition of the present embodiment or a semi-cured product of the resin composition. The prepreg of the present embodiment contains, for example, the resin composition of the present embodiment or a semi-cured product of the resin composition and a fiber base material.

[0087] The fiber substrate contained in the prepreg of this embodiment can be, for example, a known fiber substrate used in various laminates for electrical insulating materials. Examples of the material for the fiber substrate include inorganic fibers such as E-glass, D-glass, S-glass, and Q-glass; organic fibers such as polyimide, polyester, and tetrafluoroethylene; and mixtures thereof. These fiber substrates have shapes such as woven fabric, nonwoven fabric, roving, chopped strand mat, and surfacing mat. The fiber substrate is preferably in the form of a sheet.

[0088] The prepreg of this embodiment can be produced, for example, by impregnating or applying the resin composition of this embodiment to a fiber substrate and then heating and drying it to B-stage. The temperature and time for heating and drying can be, for example, 50 to 200°C and 1 to 30 minutes, from the viewpoints of productivity and appropriately B-staging the resin composition of this embodiment.

[0089] The content of the resin composition in the prepreg of the present embodiment is preferably 20 to 90% by mass, more preferably 25 to 80% by mass, and even more preferably 30 to 75% by mass, from the viewpoint that good moldability is easily obtained when the prepreg is made into a laminate.

[0090] The thickness of the prepreg of this embodiment is preferably 0.01 to 0.5 mm, more preferably 0.02 to 0.3 mm, and even more preferably 0.05 to 0.2 mm, from the viewpoint of moldability and enabling high-density wiring.

[0091] [Resin Film] The resin film of this embodiment is a resin film containing the resin composition of this embodiment or a semi-cured product of the resin composition. The resin film of this embodiment can be produced, for example, by applying the resin composition of this embodiment containing an organic solvent to a support and then heating and drying it. Examples of the support include plastic film, metal foil, and release paper. The temperature and time for heating and drying can be 50 to 200°C and 1 to 30 minutes, from the viewpoints of productivity and appropriately B-staging the resin composition of this embodiment. The resin film of this embodiment is preferably used to form an insulating layer when producing a printed wiring board.

[0092] [Laminate] The laminate of the present embodiment is a laminate having a cured product of the resin composition of the present embodiment and a metal foil. Note that a laminate having a metal foil is sometimes called a metal-clad laminate.

[0093] Examples of metals for the metal foil include copper, gold, silver, nickel, platinum, molybdenum, ruthenium, aluminum, tungsten, iron, titanium, chromium, and alloys containing one or more of these metal elements.

[0094] The laminate of this embodiment can be produced, for example, by placing a metal foil on one or both sides of the prepreg of this embodiment and then subjecting it to a heat-pressure treatment. Typically, this heat-pressure treatment hardens the B-staged prepreg to obtain the laminate of this embodiment. When performing the heat-pressure treatment, only one prepreg may be used, or two or more prepregs may be laminated together. The heat-pressure treatment can be performed using, for example, a multi-stage press, a multi-stage vacuum press, a continuous molding machine, an autoclave molding machine, or the like. The heat-pressure treatment can be performed under conditions of, for example, a temperature of 100 to 300°C, a time of 10 to 300 minutes, and a pressure of 1.5 to 5 MPa.

[0095] [Printed Wiring Board] The printed wiring board of this embodiment is a printed wiring board having a cured product of the resin composition of this embodiment. The printed wiring board of this embodiment can be produced, for example, by forming a conductor circuit on one or more materials selected from the group consisting of a cured product of the prepreg of this embodiment, a cured product of the resin film of this embodiment, and a laminate of this embodiment by a known method. Furthermore, if necessary, a multilayer printed wiring board can also be produced by further performing a multilayer adhesive process. The conductor circuit can be formed, for example, by appropriately performing a drilling process, a metal plating process, etching of a metal foil, or the like.

[0096] [Semiconductor Package] A semiconductor package according to a first aspect of the present embodiment is a semiconductor package including the printed wiring board according to the present embodiment and a semiconductor element. The semiconductor package according to the first aspect of the present embodiment can be manufactured, for example, by mounting the semiconductor element, memory, etc. on the printed wiring board according to the present embodiment by a known method.

[0097] A semiconductor package according to a second aspect of the present embodiment includes a semiconductor element and a cured product of the resin composition according to the present embodiment that encapsulates the semiconductor element. The semiconductor package according to the second aspect of the present embodiment can be produced, for example, by covering at least a portion of a semiconductor element mounted on a printed wiring board with the resin composition according to the present embodiment and curing the resin composition.

[0098] The present embodiment will be specifically described below with reference to examples, although the present embodiment is not limited to the following examples.

[0099] In each example, the weight average molecular weight (Mw) was measured by the following procedure. (Method for measuring weight average molecular weight (Mw)) The weight average molecular weight (Mw) was calculated by gel permeation chromatography (GPC) from a calibration curve using standard polystyrene. The calibration curve was approximated by a cubic equation using standard polystyrene: TSKstandard POLYSTYRENE (Types: A-2500, A-5000, F-20, F-80) [manufactured by Tosoh Corporation, trade name]. The GPC measurement conditions are shown below. Apparatus: High-speed GPC apparatus HLC-8320GPC Detector: Ultraviolet absorption detector UV-8320 [manufactured by Tosoh Corporation] Column: Guard column: TSKgel guard column Super (HZ)-M + Column: TSKgel SuperMultipore HZ-M (2 columns), Reference column: TSKgel Super H-RC (2 columns) (all manufactured by Tosoh Corporation, trade names) Column size: 4.6 x 20 mm (guard column), 4.6 x 150 mm (column), 6.0 x 150 mm (reference column) Eluent: Tetrahydrofuran Sample concentration: 10 mg / 1 mL Injection volume: 20 μL or 2 μL Flow rate: 0.35 mL / min Measurement temperature: 40°C

[0100] [Production of Aminomaleimide Resin] Production Example 1 A 2 L reactor capable of heating and cooling, equipped with a thermometer, a stirrer, and a water content monitor with a reflux condenser, was charged with 100 g of a diamine-modified siloxane at both ends (manufactured by Shin-Etsu Chemical Co., Ltd., product name: X-22-161A, a silicone compound having primary amino groups at both ends, functional group equivalent of the amino group: 800 g / mol), 450 g of 2,2-bis[4-(4-maleimidophenoxy)phenyl]propane, and 550 g of propylene glycol monomethyl ether, and the mixture was reacted at 120°C for 3 hours to produce a solution containing an aminomaleimide resin. The weight-average molecular weight (Mw) of the resulting aminomaleimide resin was 2,500.

[0101] [Production of Vinylbenzyl Compound] Production Example 2 A 500 mL reaction vessel equipped with a stirrer, thermometer, reflux condenser, and nitrogen inlet was charged with 35.6 g of indene as a base compound, 101.2 g of chloromethylstyrene (AGC Seimi Chemical Co., Ltd., a mixture of m- and p-isomers, m- and p-contents of 50% by mass), 7.1 g of tetra-n-butylammonium bromide as a phase transfer catalyst, 0.1 g of phenothiazine as a polymerization inhibitor, and 77.6 g of toluene as a solvent. The mixture was heated and stirred at 40°C while blowing in nitrogen at a flow rate of 50 mL / min. Next, a 48% by mass aqueous solution of 46.5 g of sodium hydroxide as a basic compound was added dropwise over 20 minutes, and the mixture was further stirred at 60°C for 9 hours. Nitrogen blowing was continued during the reaction. The mixture was then cooled to room temperature (25°C), neutralized with a 10% aqueous hydrochloric acid solution, and washed twice with pure water. Next, toluene was distilled off under reduced pressure, and the resulting viscous liquid was washed with methanol and then dried under vacuum to obtain vinylbenzyl compound 1. １ H-NMR analysis confirmed that the compound had a structure in which substantially all of the two hydrogen atoms directly bonded to the carbon atom at position 1 of indene represented by the following formula (B1-3) had been substituted with vinylbenzyl groups, and that it corresponded to component (B1). GPC analysis confirmed that vinylbenzyl compound 1 was a mixture of one having two vinylbenzyl groups and one having three vinylbenzyl groups, and that the weight-average molecular weight (Mw) was 500.

[0102]

[0103] [Production of Resin Composition] Examples 1 to 9 and Comparative Examples 1 to 3 Each component shown in Table 1 was mixed in powder form or mixed with methyl ethyl ketone in the amounts shown in Table 1, and the mixture was stirred and mixed at 25° C. to prepare a varnish-like resin composition (solid content concentration: approximately 60% by mass). In Table 1, the unit of the amount of each component is parts by mass, and in the case of a solution, it means parts by mass converted into solid content.

[0104] [Production of prepreg] The varnish-like resin composition obtained above was applied to a glass cloth (manufactured by Nitto Boseki Co., Ltd., trade name "T2118", thickness 0.098 mm, basis weight 114 g / m２ A prepreg was obtained by impregnating a glass (glass type: T glass) with the resin composition and drying it by heating at 110° C. for 3 minutes. The thickness of the obtained prepreg was 0.1 mm, and the content of the resin composition in the prepreg was 48.5% by mass.

[0105] [Production of Copper-Clad Laminate] Seven sheets of the prepreg obtained above were stacked, and 12 μm thick copper foil (manufactured by Mitsui Kinzoku Co., Ltd., product name "3EC-M3-VLP-12", roughened surface Rz: 3.0 μm) was placed on top and bottom of them so that the roughened surface was in contact with the prepreg. This laminate was heated and pressurized at a temperature of 240° C. and a pressure of 3.0 MPa for 100 minutes or 40 minutes to produce a copper-clad laminate (thickness: 0.7 mm).

[0106] [Evaluation and Measurement Methods] Using the copper-clad laminates prepared in each example, measurements and evaluations were carried out according to the following methods. The results are shown in Table 1.

[0107] (Method for Measuring Glass Transition Temperature and Method for Calculating the Rate of Change in Glass Transition Temperature with Heating and Pressurizing Treatment Time) The copper foil on both sides of the copper-clad laminates prepared in each example was removed by etching to obtain laminates. Among the laminates from which the copper foil was removed, those prepared using a 40-minute heating and pressurizing treatment time were designated "Laminate (40)," and those prepared using a 100-minute heating and pressurizing treatment time were designated "Laminate (100)." Each of the laminates obtained above was cut into 4 mm x 30 mm pieces in the plane direction and dried at 105°C for 1 hour to prepare test specimens. Using the test specimens as the measurement subject, dynamic viscoelasticity measurements were performed using a dynamic viscoelasticity measuring device (manufactured by UBM, product name "Rheogel-E4000") under conditions of a heating rate of 5°C / min, a frequency of 10 Hz, and a measurement temperature range of 40 to 400°C. The temperature at which tanδ reached its maximum value in the obtained temperature-loss tangent (tanδ) curve was designated the glass transition temperature (Tg). In addition, the change rate of the glass transition temperature with the heating and pressure treatment time was calculated from the glass transition temperature Tg(100) of the laminate (100) and the glass transition temperature Tg(40) of the laminate (40) using the following formula (1): Change rate of the glass transition temperature with the heating and pressure treatment time (%) = [Tg(100) - Tg(40)] x 100 / Tg(100) (1)

[0108] (Method for measuring thermal expansion coefficient) The laminate (40) and the laminate (100) were each cut into 5 mm squares and dried at 105 ° C. for 1 hour to prepare test specimens. The test specimens were attached to a thermomechanical measuring apparatus (TMA) (manufactured by TA Instruments Japan Co., Ltd., product name "TMA450") in a direction to detect displacement in the thickness direction of the laminate, and subjected to two consecutive thermomechanical analyses using a compression method under conditions of a load of 0.01 N and a temperature rise rate of 10 ° C. / min, with the first measurement temperature range being 25 to 260 ° C. and the second measurement temperature range being -20 to 300 ° C. The average thermal expansion coefficient from 30 to 260 ° C. in the second measurement was taken as the thermal expansion coefficient.

[0109] (Method for measuring flexural modulus) The laminate (40) and the laminate (100) were cut into a size of 20 mm × 50 mm in the plane direction and dried at 105 ° C. for 1 hour to prepare test specimens. The flexural modulus of the test specimens was measured at room temperature (25 ° C.) using a 5t Tensilon (manufactured by Orientec Co., Ltd., product name "RTC-1350A") at a crosshead speed of 1 mm / min and a support distance of 20 mm.

[0110]

[0111] The details of each material in Table 1 are as follows: [Component (A)] Maleimide resin 1: 2,2-bis[4-(4-maleimidophenoxy)phenyl]propane Maleimide resin 2: aminomaleimide resin obtained in Production Example 1 Maleimide resin 3: polyphenylmethane maleimide (manufactured by Daiwa Chemical Industry Co., Ltd., trade name "BMI-2300") Maleimide resin 4: 3,3'-dimethyl-5,5'-diethyl-4,4'-diphenylmethane bismaleimide Maleimide resin 5: bis(4-maleimidophenyl)methane Maleimide resin 6: biphenylaralkyl maleimide (manufactured by Nippon Kayakuhin Co., Ltd., "MIR-3000")

[0112] [Component (B)] Vinylbenzyl compound 1: Vinylbenzyl compound 1 obtained in Production Example 2 Vinylbenzyl compound 2: A mixture of a compound having two vinylbenzyl groups directly bonded to an indene ring and a vinylbenzyl compound having three vinylbenzyl groups directly bonded to an indene ring (corresponding to component (B1)) Vinylbenzyl compound 3: A mixture of a compound having two vinylbenzyl groups directly bonded to an indene ring and a vinylbenzyl compound having three vinylbenzyl groups directly bonded to an indene ring (corresponding to component (B1))

[0113] [Component (C)] Epoxy resin: Product name "HP-9540" manufactured by DIC Corporation

[0114] [Component (D)] Phenolic resin: Benzoxazine P-d, manufactured by Shikoku Chemicals Corporation

[0115] [Component (E)] Inorganic filler: spherical fused silica, average particle diameter (D ５０ ): 0.5 μm

[0116] [Component (F)] Curing accelerator: isocyanate masked imidazole (manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd., product name "G-8009L")

[0117] The results shown in Table 1 show that the resin compositions of Examples 1 to 9 of this embodiment have a small rate of change in glass transition temperature depending on the heating and pressurizing treatment time.

Claims

1. A resin composition comprising: (A) one or more components selected from the group consisting of maleimide resins and derivatives thereof having one or more N-substituted maleimide groups; and (B) a compound having a vinylbenzyl group, wherein the component (B) contains one or more components selected from the group consisting of (B1) compounds having one or more vinylbenzyl groups directly bonded to carbon atoms and (B2) compounds having three or more vinylbenzyl groups directly bonded to oxygen atoms, and the ratio of the content of the component (B) by mass to the content of the component (A) by mass [component (B) / component (A)] is 0.11 or more.

2. The resin composition according to claim 1, wherein the component (B) contains the component (B1).

3. The resin composition according to claim 2, wherein the component (B1) is a compound containing a condensed polycyclic structure containing an aromatic ring and a non-aromatic ring.

4. The resin composition according to claim 3, wherein the condensed polycyclic structure containing an aromatic ring and a non-aromatic ring is an indene ring.

5. The resin composition according to claim 2, wherein the component (B1) is a compound having two or more vinylbenzyl groups directly bonded to carbon atoms.

6. The resin composition according to any one of claims 1 to 5, wherein the component (A) is at least one selected from the group consisting of aromatic maleimide resins having two or more N-substituted maleimide groups and derivatives thereof.

7. A prepreg containing the resin composition according to any one of claims 1 to 5 or a semi-cured product of said resin composition.

8. A laminate comprising a cured product of the resin composition according to any one of claims 1 to 5 and a metal foil.

9. A resin film comprising the resin composition according to any one of claims 1 to 5 or a semi-cured product of said resin composition.

10. A printed wiring board having a cured product of the resin composition according to any one of claims 1 to 5.

11. A semiconductor package comprising the printed wiring board according to claim 10 and a semiconductor element.

12. A semiconductor package comprising a semiconductor element and a cured product of the resin composition according to any one of claims 1 to 5 that encapsulates the semiconductor element.