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

Abstract

A resin composition containing (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) a compound having a vinyl benzyl group; and a prepreg, a laminate, a resin film, a printed wiring board, and a semiconductor package using the resin composition. The 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) a compound having a vinyl benzyl group. The component (B) contains one or more compounds selected from the group consisting of (B1) compounds having three or more vinyl benzyl groups bonded to oxygen atoms and (B2) compounds having one or more vinyl benzyl groups bonded to carbon atoms.

Description

Technical Field

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

[0002] The signals used in mobile communication devices represented by mobile phones, their base station devices, network infrastructure devices such as servers and routers, and electronic devices such as large computers are becoming faster and more capacitive year by year. Along with this, dielectric properties [hereinafter sometimes referred to as "high-frequency properties"] that can reduce the transmission loss of high-frequency signals, i.e., low relative dielectric constant and low dielectric loss tangent, are being required for substrate materials, semiconductor sealing materials, etc. mounted on these electronic devices.

[0003] Substrate materials, semiconductor sealing materials, etc. are required to have heat resistance that can be tolerated in the use environment. Maleimide resin, which is one type of thermosetting resin, is used in substrate materials for printed wiring boards, etc., because of its excellent heat resistance and mechanical properties (for example, Patent Document 1).

[0004] Prior art literature

[0005] Patent Literature

[0006] Patent Document 1: Japanese Patent Application Publication No. 2009-1783 Summary of the invention

[0007] Problems to be solved by the invention

[0008] However, maleimide resins contain many polar groups and thus have a problem of poor dielectric properties, and improvements have been sought.

[0009] In view of the above situation, the present embodiment aims to provide a resin composition having excellent dielectric properties, and a prepreg, a laminate, a resin film, a printed wiring board, and a semiconductor package using the resin composition.

[0010] Means for solving problems

[0011] The present inventors have studied to solve the above-mentioned problems and have found that the problems can be solved by the following embodiments [1] to

[12] .

[0012] [1] A resin composition comprising

[0013] (A) one or more selected from maleimide resins having one or more N-substituted maleimide groups and derivatives thereof; and

[0014] (B) a compound having a vinylbenzyl group,

[0015] The component (B) contains one or more selected from (B1) a compound having three or more vinylbenzyl groups bonded to an oxygen atom, and (B2) a compound having one or more vinylbenzyl groups bonded to a carbon atom.

[0016] [2] The resin composition according to [1], wherein

[0017] The component (B) contains the component (B1),

[0018] The component (B1) is a compound containing a structural unit represented by the following general formula (B-1).

[0019] [Chemical formula 1]

[0020]

[0021] [3] The resin composition according to [1], wherein

[0022] The component (B) contains the component (B2),

[0023] The component (B2) is a compound including a condensed polycyclic structure including an aromatic ring and a non-aromatic ring.

[0024] [4] The resin composition according to [3], wherein

[0025] The fused polycyclic structure including an aromatic ring and a non-aromatic ring is an indene ring.

[0026] [5] The resin composition according to any one of [1] to [4], wherein

[0027] The component (A) is an aromatic bismaleimide resin having two N-substituted maleimide groups.

[0028] [6] The resin composition according to any one of [1] to [5], wherein

[0029] The content ratio of the N-substituted maleimide group derived from the component (A) to the vinyl group derived from the component (B) [N-substituted maleimide group / vinyl group] is 0.05 to 5 on a molar basis.

[0030] [7] A prepreg comprising the resin composition according to any one of [1] to [6] above or a semi-cured product of the resin composition.

[0031] [8] A laminate comprising a cured product of the resin composition according to any one of [1] to [6] above and a metal foil.

[0032] [9] A resin film comprising the resin composition according to any one of [1] to [6] or a semi-cured product of the resin composition.

[0033]

[10] A printed wiring board comprising a cured product of the resin composition according to any one of [1] to [6].

[0034]

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

[10] and a semiconductor element.

[0035]

[12] A semiconductor package comprising a semiconductor element and a cured product of the resin composition according to any one of [1] to [6] above that seals the semiconductor element.

[0036] Effects of the Invention

[0037] According to the present embodiment, it is possible to provide a resin composition having excellent dielectric properties, and a prepreg, a laminate, a resin film, a printed wiring board, and a semiconductor package using the resin composition. DETAILED DESCRIPTION

[0038] In the present specification, a numerical range expressed by "to" means a range including the numerical values ​​described before and after "to" as the minimum value and the maximum value, respectively.

[0039] For example, a numerical range such as "X to Y" (X, Y are real numbers) refers to a numerical range greater than X and less than Y. In addition, a description such as "greater than X" in this specification refers to X and a numerical value greater than X. In addition, a description such as "less than Y" in this specification refers to Y and a numerical value less than Y.

[0040] The lower limit value and the upper limit value of the numerical range described in the present specification can be arbitrarily combined with the lower limit value or the upper limit value of other numerical ranges, respectively.

[0041] In the numerical range described in the present specification, the lower limit value or the upper limit value of the numerical range may be replaced with the value shown in the Examples.

[0042] Each component and material exemplified in the present specification may be used alone or in combination of two or more unless otherwise specified.

[0043] In the present specification, when there are plural kinds of substances corresponding to the components in the resin composition, the content of each component in the resin composition refers to the total amount of the plural kinds of substances present in the resin composition unless otherwise specified.

[0044] In this specification, "solid content" refers to non-volatile components other than volatile substances such as solvents. That is, "solid content" refers to components that remain when the resin composition is dried without volatilization, and also includes components that are liquid, syrupy, and waxy at room temperature. Here, room temperature in this specification refers to 25°C.

[0045] The weight average molecular weight (Mw) and number average molecular weight (Mn) in this specification refer to the values ​​measured by gel permeation chromatography (GPC) in terms of polystyrene. Specifically, the weight average molecular weight (Mw) and number average molecular weight (Mn) in this specification can be measured by the method described in Examples.

[0046] In the present specification, the "semi-cured product" is synonymous with the resin composition in the B-stage state in JIS K 6800 (1985), and the "cured product" is synonymous with the resin composition in the C-stage state in JIS K 6800 (1985).

[0047] The mechanism of action described in this specification is a guess and is not intended to limit the mechanism for achieving the effects of the present embodiment.

[0048] A mode in which the matters described in this specification are arbitrarily combined is also included in this embodiment.

[0049] [Resin composition]

[0050] The resin composition of this embodiment contains

[0051] (A) one or more selected from maleimide resins having one or more N-substituted maleimide groups and derivatives thereof, and

[0052] (B) Compounds having a vinylbenzyl group

[0053] A resin composition,

[0054] The component (B) contains one or more selected from (B1) a compound having three or more vinylbenzyl groups bonded to an oxygen atom, and (B2) a compound having one or more vinylbenzyl groups bonded to a carbon atom.

[0055] In addition, in this specification, each component may be abbreviated as (A) component, (B) component, etc., and the same abbreviations may be used for other components.

[0056] <(A) Maleimide-based resin>

[0057] (A) The maleimide resin is one or more selected from the group consisting of a maleimide resin having one or more N-substituted maleimide groups and a derivative of the maleimide resin.

[0058] (A) The maleimide resin may be used alone or in combination of two or more.

[0059] In addition, in the following description, the maleimide resin which has one or more N-substituted maleimide groups may be referred to as "maleimide resin (AX)" or "(AX) component".

[0060] In addition, 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 a "(AY) component".

[0061] (Maleimide resin (AX))

[0062] The maleimide resin (AX) is not particularly limited as long as it is a maleimide resin having one or more N-substituted maleimide groups.

[0063] 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, from the viewpoint of conductor adhesion and heat resistance.

[0064] It should be noted that in this specification, "aromatic maleimide resin" refers to a compound having an N-substituted maleimide group directly bonded to an aromatic ring. In addition, in this specification, "aromatic bismaleimide resin" refers to a compound having two N-substituted maleimide groups directly bonded to an aromatic ring. In addition, in this specification, "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, "aliphatic maleimide resin" refers to a compound having an N-substituted maleimide group directly bonded to an aliphatic hydrocarbon.

[0065] As the maleimide resin (AX), a maleimide resin represented by the following general formula (A-1) is preferred.

[0066] [Chemical formula 2]

[0067]

[0068] (Where X A1 It is a divalent organic group.

[0069] X in the above general formula (A-1) A1It is a divalent organic group.

[0070] As X in the above general formula (A-1) A1 The divalent organic group represented by the following general formula (A-2) includes, for example, a divalent organic group represented by the following general formula (A-3), a divalent organic group represented by the following general formula (A-4), a divalent organic group represented by the following general formula (A-5), a divalent organic group represented by the following general formula (A-6), a divalent organic group represented by the following general formula (A-7), etc.

[0071] [Chemical formula 3]

[0072]

[0073] (Where 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. * indicates a bonding site. )

[0074] As R in the above general formula (A-2) A1 The aliphatic hydrocarbon group having 1 to 5 carbon atoms represented by , for example, includes alkyl groups having 1 to 5 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-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 straight-chain or branched. As the aliphatic hydrocarbon group having 1 to 5 carbon atoms, an aliphatic hydrocarbon group having 1 to 3 carbon atoms is preferred, an alkyl group having 1 to 3 carbon atoms is more preferred, and a methyl group is further preferred.

[0075] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0076] In the above general formula (A-2), n A1 It is an integer of 0 to 4, preferably an integer of 0 to 2, more preferably 0 or 1, and even more preferably 0, from the viewpoint of easy availability.

[0077] n A1 When the integer is 2 or more, multiple R A1 It can be the same or different.

[0078] [Chemical formula 4]

[0079]

[0080] (Where R A2 and R A3 Each independently represents an aliphatic hydrocarbon group having 1 to 5 carbon atoms or a halogen atom. A2It is an alkylene group having 1 to 5 carbon atoms, an alkylidene group having 2 to 5 carbon atoms, an ether group, a thioether 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 Each independently represents an integer of 0 to 4. * represents a bonding site. )

[0081] As R in the above general formula (A-3) A2 and R A3 The aliphatic hydrocarbon group having 1 to 5 carbon atoms represented by , for example, includes alkyl groups having 1 to 5 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-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 straight-chain or branched. As the aliphatic hydrocarbon group having 1 to 5 carbon atoms, an aliphatic hydrocarbon group having 1 to 3 carbon atoms is preferred, an alkyl group having 1 to 3 carbon atoms is more preferred, and a methyl group and an ethyl group are further preferred.

[0082] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0083] As X in the above general formula (A-3) A2 The alkylene group having 1 to 5 carbon atoms represented by , for example, includes methylene, 1,2-ethylene, 1,3-propylene, 1,4-butylene, 1,5-pentylene, etc. As the alkylene group having 1 to 5 carbon atoms, an alkylene group having 1 to 3 carbon atoms is preferred, an alkylene group having 1 or 2 carbon atoms is more preferred, and a methylene group is further preferred.

[0084] As X in the above general formula (A-3) A2 The alkylidene group having 2 to 5 carbon atoms represented by alkylidene group includes, for example, ethylidene group, propylidene group, isopropylidene group, butylidene group, isobutylidene group, pentylidene group, isopentylidene group, etc. Among them, the alkylidene group having 2 to 4 carbon atoms is preferred, the alkylidene group having 2 or 3 carbon atoms is more preferred, and the isopropylidene group is further preferred.

[0085] In the above general formula (A-3), n A2 and n A3 Each independently represents an integer from 0 to 4.

[0086] n A2 or A3 When the integer is 2 or more, multiple R A2 Each other or multiple R A3 They may be the same as or different from each other.

[0087] X in the above general formula (A-3) A2 The divalent organic group represented by the general formula (A-3-1) is as follows.

[0088] [Chemical formula 5]

[0089]

[0090] (Where R A4 and R A5 Each independently represents an aliphatic hydrocarbon group having 1 to 5 carbon atoms or a halogen atom. A3 It is an alkylene group having 1 to 5 carbon atoms, an alkylidene group having 2 to 5 carbon atoms, an ether group, a thioether group, a sulfonyl group, a carbonyloxy group, a keto group or a single bond. A4 and n A5 Each independently represents an integer of 0 to 4. * represents a bonding site. )

[0091] As R in the above general formula (A-3-1) A4 and R A5 The aliphatic hydrocarbon group having 1 to 5 carbon atoms represented by , for example, includes alkyl groups having 1 to 5 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-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 straight-chain or branched. As the aliphatic hydrocarbon group having 1 to 5 carbon atoms, an aliphatic hydrocarbon group having 1 to 3 carbon atoms is preferred, an alkyl group having 1 to 3 carbon atoms is more preferred, and a methyl group is further preferred.

[0092] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0093] As X in the above general formula (A-3-1) A3 The alkylene group having 1 to 5 carbon atoms represented by , for example, includes methylene, 1,2-ethylene, 1,3-propylene, 1,4-butylene, 1,5-pentylene, etc. As the alkylene group having 1 to 5 carbon atoms, an alkylene group having 1 to 3 carbon atoms is preferred, an alkylene group having 1 or 2 carbon atoms is more preferred, and a methylene group is further preferred.

[0094] As X in the above general formula (A-3-1) A3 The alkylidene group having 2 to 5 carbon atoms represented by alkylidene group includes, for example, ethylidene group, propylidene group, isopropylidene group, butylidene group, isobutylidene group, pentylidene group, isopentylidene group, etc. Among them, the alkylidene group having 2 to 4 carbon atoms is preferred, the alkylidene group having 2 or 3 carbon atoms is more preferred, and the isopropylidene group is further preferred.

[0095] In the above general formula (A-3-1), n A4 and n A5 Each independently represents an integer of 0 to 4, and is preferably an integer of 0 to 2, more preferably 0 or 1, and even more preferably 0, from the viewpoint of easy availability.

[0096] n A4 or A5 When the integer is 2 or more, multiple RA4 Each other or multiple R A5 They may be the same as or different from each other.

[0097] As X in the above general formula (A-3) A2 Among the above options, preferred are an alkylene group having 1 to 5 carbon atoms, an alkylidene group having 2 to 5 carbon atoms, and a divalent organic group represented by the above general formula (A-3-1), more preferred are an alkylene group having 1 to 5 carbon atoms, and still more preferred are methylene groups.

[0098] [Chemical formula 6]

[0099]

[0100] (where n A6 is an integer from 0 to 10. * indicates a bonding site. )

[0101] In the above general formula (A-4), n A6 From the viewpoint of easy availability, an integer of 0 to 5 is preferred, an integer of 0 to 4 is more preferred, and an integer of 0 to 3 is further preferred.

[0102] [Chemical formula 7]

[0103]

[0104] (where n A7 It is a number from 0 to 5. * indicates a bonding site. )

[0105] [Chemical formula 8]

[0106]

[0107] (Where R A6 and R A7 Each independently represents a hydrogen atom or an aliphatic hydrocarbon group having 1 to 5 carbon atoms. A8 is an integer from 1 to 8. * represents a bonding site. )

[0108] As R in the above general formula (A-6) A6 and R A7 The aliphatic hydrocarbon group having 1 to 5 carbon atoms represented by , for example, includes alkyl groups having 1 to 5 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-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 straight-chain or branched.

[0109] In the above general formula (A-6), n A8 It is an integer of 1 to 8, preferably an integer of 1 to 5, more preferably an integer of 1 to 3, and further preferably 1. A8When the integer is 2 or more, multiple R A6 Each other or multiple R A7 They may be the same as or different from each other.

[0110] [Chemical formula 9]

[0111]

[0112] (Where R A8 is an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, 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, and n A9 is an integer from 0 to 3. A9 ~R A11 Each R is independently an alkyl group having 1 to 10 carbon atoms. A12 Each is independently an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, 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. A10 Each independently represents an integer from 0 to 4, and n A11 It is a value between 0.95 and 10.0.

[0113] *Indicates bonding location. )

[0114] As R in the above general formula (A-7) A8 Examples of the alkyl group having 1 to 10 carbon atoms include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, and decyl. These alkyl groups may be linear or branched.

[0115] As R A8 Examples of the alkyl group contained in the alkoxy group having 1 to 10 carbon atoms and the alkylthio group having 1 to 10 carbon atoms include the same groups as those mentioned above for the alkyl group having 1 to 10 carbon atoms.

[0116] As R A8 Examples of the aryl group having 6 to 10 carbon atoms include phenyl and naphthyl.

[0117] As R A8 Examples of the aryl group contained in the aryloxy group having 6 to 10 carbon atoms and the arylthio group having 6 to 10 carbon atoms include the same groups as those mentioned above for the aryl group having 6 to 10 carbon atoms.

[0118] As R A8 Examples of the cycloalkyl group having 3 to 10 carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl and cyclodecyl.

[0119] In the above general formula (A-7), n A9 When R is an integer from 1 to 3, A8 From the viewpoint of solvent solubility and reactivity, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or an aryl group having 6 to 10 carbon atoms is preferred, and an alkyl group having 1 to 4 carbon atoms is more preferred.

[0120] As R A9 ~R A119 The alkyl group having 1 to 10 carbon atoms represented by , for example, includes methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, decyl, etc. These alkyl groups may be straight-chain or branched. A9 ~R A119 An alkyl group having 1 to 4 carbon atoms is preferred, a methyl group or an ethyl group is more preferred, and a methyl group is further preferred.

[0121] In the above general formula (A-7), n A9 is an integer from 0 to 3, where n A9 If the value is 2 or 3, multiple R A8 They can be the same or different.

[0122] Among the above, the divalent organic group represented by the general formula (A-7) is preferably n A9 0, R A9 ~R A11 A divalent organic group which is a methyl group.

[0123] In the above general formula (A-7), a plurality of R A8 Each other, multiple R A12 Each other, multiple n A9 Each other, multiple n A10 Each of them may be the same or different. A119 If more than 1, multiple R A9 Each other, multiple R A10 Each other and multiple R A119 Each of them can be the same or different.

[0124] Regarding R in the above general formula (A-7): A12 The explanations of the alkyl group having 1 to 10 carbon atoms, the alkoxy group having 1 to 10 carbon atoms, the alkylthio group having 1 to 10 carbon atoms, the aryl group having 6 to 10 carbon atoms, the aryloxy group having 6 to 10 carbon atoms, the arylthio group having 6 to 10 carbon atoms, and the cycloalkyl group having 3 to 10 carbon atoms represented by R are the same as those for the above R. A8The same as the descriptions of the alkyl group having 1 to 10 carbon atoms, the alkoxy group having 1 to 10 carbon atoms, the alkylthio group having 1 to 10 carbon atoms, the aryl group having 6 to 10 carbon atoms, the aryloxy group having 6 to 10 carbon atoms, the arylthio group having 6 to 10 carbon atoms and the cycloalkyl group having 3 to 10 carbon atoms.

[0125] Among these, R A12 From the viewpoint of compatibility with other resins, solvent solubility, dielectric properties, adhesion to conductors and ease of production, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or an aryl group having 6 to 10 carbon atoms is preferred, and an alkyl group having 1 to 3 carbon atoms is more preferred.

[0126] In the above general formula (A-7), n A10 It is an integer of 0 to 4, preferably an integer of 0 to 3, and more preferably 0 or 2, from the viewpoint of compatibility with other resins, solvent solubility, dielectric properties, adhesion to a conductor, and ease of production.

[0127] It should be noted that by making n A10 When n is 1 or more, the benzene ring and the N-substituted maleimide group have a distorted conformation, and the solvent solubility tends to be further improved due to the inhibition of intermolecular stacking. A10 When R is greater than 1, A12 The substitution position is preferably the ortho position relative to the N-substituted maleimide group.

[0128] In the above general formula (A-7), n A11 From the viewpoint of compatibility with other resins, solvent solubility, melt viscosity, handling properties and heat resistance, it is preferably 0.98 to 8.0, more preferably 1.0 to 7.0, and even more preferably 1.1 to 6.0.

[0129] Preferred examples of the divalent organic group represented by the general formula (A-7) include a divalent organic group represented by the following general formula (A-7-1), a divalent organic group represented by the following general formula (A-7-2), a divalent organic group represented by the following general formula (A-7-3), and a divalent organic group represented by the following general formula (A-7-4).

[0130] [Chemical formula 10]

[0131]

[0132] (where n A11 Same as in the above general formula (A-7). * indicates a bonding site. )

[0133] In the maleimide resin represented by the above general formula (A-1), it is preferred that the maleimide resin has a divalent organic group represented by the above general formula (A-3) as X A1The maleimide resin preferably has a divalent organic group represented by the above general formula (A-7) as X A1 of maleimide resin.

[0134] Examples of the maleimide resin (AX) include aromatic bismaleimide resins, aromatic polymaleimide resins, aliphatic maleimide resins, and the like. Among them, aromatic bismaleimide resins are preferred.

[0135] Specific examples of the maleimide resin (AX) include N,N'-ethylenebismaleimide, N,N'-hexamethylenebismaleimide, N,N'-(1,3-phenylene)bismaleimide, N,N'-[1,3-(2-methylphenylene)]bismaleimide, N,N'-[1,3-(4-methylphenylene)]bismaleimide, N,N'-(1,4-phenylene)bismaleimide, bis(4-maleimidophenyl)methane, bis(3-methyl-4-maleimidophenyl)methane, 3,3'-dimethyl-5,5'-diethyl-4,4'-diphenylmethanebismaleimide, bis(4-maleimidophenyl)ether, bis(4-maleimidophenyl)sulfone, bis(4-maleimidophenyl)sulfide, bis(4-maleimidophenyl)ketone, bis(4-maleimidocyclohexyl)methane, 1,4-bis(4-maleimidophenyl)cyclohexane, 1,4-bis(maleimidomethyl)cyclohexane, 1,4-bis(maleimidomethyl)benzene, 1,3-bis(4-maleimidophenoxy)benzene, 1,3-bis(3-maleimidophenoxy)benzene, bis[4-(3-maleimidophenoxy)phenyl]methane, bis[4-(4-maleimidophenoxy)phenyl]methane, 1,1-bis[4-(3-maleimidophenoxy)phenyl]ethane, 1,1-bis[4-(4-maleimidophenoxy)phenyl]ethane, 1,2-bis[4-(3-maleimidophenoxy)phenyl]ethane 1,2-bis[4-(4-maleimidophenoxy)phenyl]ethane, 2,2-bis[4-(3-maleimidophenoxy)phenyl]propane, 2,2-bis[4-(4-maleimidophenoxy)phenyl]propane, 2,2-bis[4-(3-maleimidophenoxy)phenyl]butane, 2,2-bis[4-(4-maleimidophenoxy)phenyl]butane, 2,2-bis[4-(3-maleimidophenoxy)phenyl]-1,1,1,3,3,3-hexafluoropropane, 2,2-bis[4-(4-maleimidophenoxy)phenyl]-1,1,1,3,3,3-hexafluoropropane, 4,4-bis(3-maleimidophenoxy)biphenyl, 4,4- Bis(4-maleimidophenoxy)biphenyl, bis[4-(3-maleimidophenoxy)phenyl]ketone, bis[4-(4-maleimidophenoxy)phenyl]ketone, bis(4-maleimidophenyl)disulfide, bis[4-(3-maleimidophenoxy)phenyl]sulfide, bis[4-(4-maleimidophenoxy)phenyl]sulfide, bis[4-(3-maleimidophenoxy)phenyl]sulfoxide, bis[4-(4-maleimidophenoxy)phenyl]sulfoxide, bis[4-(3-maleimidophenoxy)phenyl]sulfone, bis[4-(4-maleimidophenoxy)phenyl]sulfone, bis[4-(3-maleimidophenoxy)phenyl]ether, bis[4-(4-maleimidophenoxy)phenyl]ether, 1,4-bis[4-(4-maleimidophenoxy)-α,α-dimethylbenzyl]benzene, 1,3-bis[4-(4-maleimidophenoxy)-α,α-dimethylbenzyl]benzene, 1,4-bis[4-(3-maleimidophenoxy)-α,α-dimethylbenzyl]benzene, 1,3-bis[4-(3-maleimidophenoxy)-α,α-dimethylbenzyl]benzene, 1,4-bis[4-(4-maleimidophenoxy)-3,5-dimethyl-α,α-dimethylbenzyl] benzene, 1,3-bis[4-(4-maleimide phenoxy)-3,5-dimethyl-α,α-dimethylbenzyl]benzene, 1,4-bis[4-(3-maleimide phenoxy)-3,5-dimethyl-α,α-dimethylbenzyl]benzene, 1,3-bis[4-(3-maleimide phenoxy)-3,5-dimethyl-α,α-dimethylbenzyl]benzene, polyphenylmethane maleimide, aromatic bismaleimide resins having an indane skeleton, biphenyl aralkyl type maleimide resins, etc. Among them, bis(4-maleimide phenyl)methane and aromatic bismaleimide resins having an indane skeleton are preferred.

[0136] (Maleimide resin derivative (AY))

[0137] As the maleimide resin derivative (AY), an aminomaleimide resin containing a structural unit derived from the maleimide resin (AX) and a structural unit derived from a diamine compound is preferred.

[0138] Examples of the structural unit derived from the maleimide resin (AX) contained in the aminomaleimide resin include structural units formed by Michael addition reaction between at least one N-substituted maleimide group contained in the maleimide resin (AX) and an amino group contained in a diamine compound.

[0139] The structural unit derived from the maleimide resin (AX) contained in the aminomaleimide resin may be a single type or two or more types.

[0140] Examples of the structural unit derived from the diamine compound contained in the aminomaleimide resin include a structural unit obtained by Michael addition reaction of one or both of the two amino groups contained in the diamine compound and the N-substituted maleimide group contained in the maleimide resin (AX).

[0141] The structural unit derived from the diamine compound contained in the aminomaleimide resin may be a single type or two or more types.

[0142] Examples of the diamine compound include 4,4'-diaminodiphenylmethane, 3,3'-dimethyl-4,4'-diaminodiphenylmethane, 3,3'-diethyl-4,4'-diaminodiphenylmethane, 4,4'-diaminodiphenyl ether, 4,4'-diaminodiphenyl sulfone, 3,3'-diaminodiphenyl sulfone, 4,4'-diaminodiphenyl ketone, 4,4'-diaminobiphenyl, 3,3'-diaminodiphenyl sulfone, methyl-4,4'-diaminobiphenyl, 2,2'-dimethyl-4,4'-diaminobiphenyl, 3,3'-dihydroxybenzidine, 2,2-bis(3-amino-4-hydroxyphenyl)propane, 3,3'-dimethyl-5,5'-diethyl-4,4'-diaminodiphenylmethane, 2,2-bis(4-aminophenyl)propane, 2,2-bis[4-(4-aminophenoxy)phenyl]propane, 1,3-bis (3-aminophenoxy)benzene, 1,3-bis(4-aminophenoxy)benzene, 1,4-bis(4-aminophenoxy)benzene, 4,4'-bis(4-aminophenoxy)biphenyl, 1,3-bis[1-[4-(4-aminophenoxy)phenyl]-1-methylethyl]benzene, 1,4-bis[1-[4-(4-aminophenoxy)phenyl]-1-methylethyl]benzene, 4,4'-[1,3-phenylenebis(1- Aromatic diamine compounds such as bis(4-(4-aminophenoxy)phenyl)sulfone, bis(4-(3-aminophenoxy)phenyl)sulfone and 9,9-bis(4-aminophenyl)fluorene; and organosilicon compounds having two primary amino groups.

[0143] In addition, in this specification, an "aromatic diamine compound" means a compound which has two amino groups directly bonded to an aromatic ring.

[0144] ((A) Content of maleimide resin)

[0145] The content of the (A) maleimide resin in the resin composition of the present embodiment is not particularly limited, but is preferably 10 to 90% by mass, more preferably 15 to 85% by mass, and further preferably 20 to 80% by mass, relative to the total amount (100% by mass) of the resin components in the resin composition of the present embodiment.

[0146] When the content of the maleimide resin (A) is above the lower limit, the heat resistance, formability, processability and conductor adhesion tend to be improved. In addition, when the content of the maleimide resin (A) is below the upper limit, the dielectric properties tend to be improved.

[0147] Here, the "resin component" in this specification refers to a resin and a compound that forms a resin by a curing reaction.

[0148] For example, in the resin composition of the present embodiment, the (A) component and the (B) component correspond to the resin component.

[0149] When the resin composition of the present embodiment contains a resin or a compound that forms a resin by a curing reaction as an arbitrary component in addition to the above-mentioned components, these arbitrary components are also included in the resin component.

[0150] <(B) Compounds Having a Vinylbenzyl Group>

[0151] The (B) compound having a vinylbenzyl group (hereinafter also referred to as "(B) vinylbenzyl compound") contains one or more selected from (B1) a compound having three or more vinylbenzyl groups bonded to oxygen atoms, and (B2) a compound having one or more vinylbenzyl groups bonded to carbon atoms.

[0152] The vinyl group as a reactive group of the vinylbenzyl compound (B) has a lower polarity than the N-substituted maleimide group of the component (A). Therefore, the resin composition of the present embodiment containing the vinylbenzyl compound (B) can express excellent dielectric properties.

[0153] The component (B) may be used alone or in combination of two or more.

[0154] The vinylbenzyl group of the component (B) may be any of an o-vinylbenzyl group, a m-vinylbenzyl group, and a p-vinylbenzyl group, but is preferably a p-vinylbenzyl group from the viewpoint of dielectric properties.

[0155] The content of the vinylbenzyl groups in all the vinylbenzyl groups in the component (B) is not particularly limited, but is preferably 10 to 100 mass %, more preferably 15 to 95 mass %, further preferably 20 to 90 mass %, and particularly preferably 25 to 85 mass % from the viewpoint of low dielectric loss tangent.

[0156] ((B1) Compound having 3 or more vinylbenzyl groups bonded to oxygen atoms)

[0157] The component (B1) is not particularly limited as long as it is a compound having three or more vinylbenzyl groups directly bonded to an oxygen atom.

[0158] The resin composition of the present embodiment contains the component (B1) as the component (B), thereby obtaining excellent dielectric properties and improving curability.

[0159] The number of vinylbenzyl groups bonded to oxygen atoms in the component (B1) per molecule is 3 or more, but is preferably 50 or less, and more preferably 30 or less, from the viewpoint of solvent solubility.

[0160] The weight average molecular weight (Mw) of the component (B1) is not particularly limited, but is preferably 300 to 50,000, more preferably 500 to 30,000, and even more preferably 1,000 to 10,000 from the viewpoint of moldability and handling properties.

[0161] The component (B) contains the component (B1), and the component (B1) is preferably a compound containing a structural unit represented by the following general formula (B1-1) from the viewpoints of curability, moldability, and handleability.

[0162] [Chemical formula 11]

[0163]

[0164] It is preferred that all the vinylbenzyl groups bonded to oxygen atoms in the component (B1) are groups contained in the structural unit represented by the above-mentioned general formula (B1-1).

[0165] The component (B1) containing the structural unit represented by the above general formula (B1-1) is preferably a compound represented by the following general formula (B1-2).

[0166] [Chemical formula 12]

[0167]

[0168] (Where X B1 Each independently is a divalent hydrocarbon group, n B1 is an integer from 1 to 5.)

[0169] As X in the above general formula (B1-2) B1 Examples of the divalent hydrocarbon group represented by include an alkylene group having 1 to 5 carbon atoms, an alkylidene group having 2 to 5 carbon atoms, a divalent alicyclic hydrocarbon group having 5 to 12 carbon atoms, an arylene group having 6 to 12 carbon atoms, and a divalent group composed of a combination of these.

[0170] Examples of the alkylene group having 1 to 5 carbon atoms include a methylene group, an ethylene group, a propylene group, a propylene group, a butylene group, and a pentylene group.

[0171] Examples of the alkylidene group having 2 to 5 carbon atoms include ethylidene, propylidene, isopropylidene, butylidene, isobutylidene, pentylidene and isopentylidene.

[0172] Examples of the divalent alicyclic hydrocarbon group 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, and saturated dicyclopentadiene.

[0173] Examples of the arylene group having 6 to 12 carbon atoms include a phenylene group, a naphthylene group, and a biphenylene group.

[0174] X B1 It is preferably a group formed by combining an alkylene group having 1 to 5 carbon atoms and an arylene group having 6 to 12 carbon atoms, and more preferably a divalent group represented by the following general formula (B1-2-1).

[0175] [Chemical formula 13]

[0176] *-X B2 -Ar B1 -X B2 -* (B1-2-1)

[0177] (Where X B2 are each independently an alkylene group having 1 to 5 carbon atoms, Ar B1 It is an arylene group having 6 to 12 carbon atoms. * indicates a bonding site. )

[0178] X B2 The alkylene group having 1 to 5 carbon atoms represented by the present invention is preferably a methylene group among the groups exemplified above.

[0179] Ar B1 The arylene group having 6 to 12 carbon atoms represented by is preferably phenylene or biphenylene among the above-mentioned groups. In addition, the phenylene group is preferably 1,4-phenylene, and the biphenylene group is preferably 4,4'-biphenylene.

[0180] In the above general formula (B1-2), n B1 It is an integer of 1-50, preferably an integer of 1-30, and more preferably an integer of 1-20.

[0181] ((B2) Compounds having one or more vinylbenzyl groups bonded to a carbon atom)

[0182] The component (B2) is not particularly limited as long as it is a compound having one or more vinylbenzyl groups directly bonded to a carbon atom.

[0183] The resin composition of the present embodiment can obtain particularly excellent dielectric properties by containing the component (B2) as the component (B).

[0184] The number of vinylbenzyl groups bonded to carbon atoms in the component (B2) may be one or more in one molecule, but is preferably 2 to 4, and more preferably 2 or 3.

[0185] The weight average molecular weight (Mw) of the component (B2) is not particularly limited, but is preferably 200 to 800, more preferably 250 to 750, and even more preferably 300 to 700 from the viewpoint of moldability and handleability.

[0186] The component (B) contains the component (B2), and the component (B2) is preferably a compound containing a condensed polycyclic structure containing an aromatic ring and a non-aromatic ring.

[0187] Examples of the fused polycyclic structure including an aromatic ring and a non-aromatic ring of the component (B2) include a fluorene ring, an indene ring, an indane ring, a phenanthrene ring, an acenaphthene ring, etc. Among them, a fluorene ring and an indene ring are preferred from the viewpoint of dielectric properties.

[0188] As the component (B2) containing a fluorene ring, a compound represented by the following general formula (B2-1) is preferred from the viewpoint of dielectric properties.

[0189] [Chemical formula 141

[0190]

[0191] (Where X B3 is an alkylene group having 1 to 10 carbon atoms, R B1 is a hydrogen atom or a vinylbenzyl group. )

[0192] As X in the above general formula (B2-1) B3 Examples of the alkylene group having 1 to 10 carbon atoms include methylene, 1,2-ethylene, 1,3-propylene, 1,4-butylene, 1,5-pentylene, and 1,6-hexylene.

[0193] As the component (B2) containing an indene ring, a compound represented by the following general formula (B2-2) is preferred from the viewpoint of dielectric properties.

[0194] [Chemical formula 15]

[0195]

[0196] (Where R B2 Each is independently a vinylbenzyl group, n b2 is an integer from 1 to 3.)

[0197] The compound represented by the general formula (B2-2) 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. In the case of a mixture, the average number of vinylbenzyl groups per molecule of the compound represented by the general formula (B2-2) is preferably 1.4 to 2.8, more preferably 1.6 to 2.7, and even more preferably 1.8 to 2.6.

[0198] As the component (B), a commercially available product may be used, or a product synthesized by a known method may be used.

[0199] As a method for synthesizing component (B), for example, a method of reacting a base compound into which a vinylbenzyl group is introduced with styrene having a halomethyl group in the presence of a basic compound can be cited. Examples of the base compound include compounds having a phenolic hydroxyl group; compounds having a condensed polycyclic structure including an aromatic ring such as fluorene, indene, indane, phenanthrene, acenaphthene, and the like and a non-aromatic ring; and the like.

[0200] Examples of the styrene having a halomethyl group include o-chloromethylstyrene, m-chloromethylstyrene, p-chloromethylstyrene, and mixtures thereof.

[0201] Examples of the basic compound include alkali metal hydroxides and alkali metal alkoxides.

[0202] A phase transfer catalyst may be used in the above reaction. Examples of the phase transfer catalyst include tetrabutylammonium bromide.

[0203] The reaction is preferably carried out under heating and stirring, and the obtained product can be purified by a known method such as concentration, reprecipitation, washing, etc. as necessary.

[0204] The total content of one or more selected from the components (B1) and (B2) in the component (B) is not particularly limited, but is preferably 80 to 100% by mass, more preferably 90 to 100% by mass, and even more preferably 95 to 100% by mass based on the total amount of the component (B), from the viewpoint of dielectric properties.

[0205] ((B) Content of vinyl benzyl compound)

[0206] The content of the (B) vinylbenzyl compound in the resin composition of the present embodiment is not particularly limited, but is preferably 10 to 90% by mass, more preferably 15 to 85% by mass, and even more preferably 20 to 80% by mass, relative to the total amount (100% by mass) of the resin components in the resin composition of the present embodiment.

[0207] When the content of the vinylbenzyl compound (B) is at least the above lower limit, the dielectric properties tend to be more favorable. When the content of the vinylbenzyl compound (B) is at most the above upper limit, the conductor adhesion tends to be more favorable.

[0208] The content ratio of the N-substituted maleimide group derived from the component (A) to the vinyl group derived from the component (B) [N-substituted maleimide group / vinyl group] in the resin composition of the present embodiment is not particularly limited, but is preferably 0.05 to 5, more preferably 0.10 to 3, and even more preferably 0.15 to 1.2 on a molar basis from the viewpoint of dielectric properties, curability, formability and conductor adhesion.

[0209] In addition, the content ratio [N-substituted maleimide group / vinyl group] may be 1.0 or less, 0.6 or less, 0.4 or less, or 0.3 or less on a molar basis from the viewpoint of dielectric properties.

[0210] <Other ingredients>

[0211] The resin composition of the present embodiment may contain other components other than the above-mentioned components as necessary, or may not contain them.

[0212] Examples of other components include elastomers, inorganic fillers, curing accelerators, organic solvents, and other additives.

[0213] The other components may be used alone or in combination of two or more.

[0214] (Elastomer)

[0215] Examples of the elastomer include styrene-based elastomers, olefin-based elastomers, urethane-based elastomers, polyester-based elastomers, polyamide-based elastomers, acrylic elastomers, silicone-based elastomers, and derivatives thereof.

[0216] (Inorganic filler)

[0217] Examples of the inorganic filler include silicon dioxide, aluminum oxide, titanium oxide, mica, beryllium oxide, 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, and silicon carbide.

[0218] (Curing accelerator)

[0219] Examples of the curing accelerator include acidic catalysts such as p-toluenesulfonic acid; amine compounds such as triethylamine, pyridine, and tributylamine; imidazole compounds such as methylimidazole and phenylimidazole; isocyanate-masked imidazole compounds such as an addition reaction product of hexamethylene diisocyanate resin and 2-ethyl-4-methylimidazole; tertiary amine compounds; quaternary ammonium compounds; phosphorus compounds such as triphenylphosphine; organic peroxides such as diisopropyl peroxide, 2,5-dimethyl-2,5-bis(tert-butylperoxy)hex-3-yne, 2,5-dimethyl-2,5-bis(tert-butylperoxy)hexane, tert-butylperoxyisopropyl monocarbonate, and α,α'-bis(tert-butylperoxy)diisopropylbenzene; and carboxylates of manganese, cobalt, zinc, and the like.

[0220] (Organic Solvent)

[0221] Examples of the organic solvent 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; ether solvents such as tetrahydrofuran; aromatic hydrocarbon solvents such as toluene, xylene, and mesitylene; nitrogen atom-containing solvents such as dimethylformamide, dimethylacetamide, and N-methylpyrrolidone; sulfur atom-containing solvents such as dimethyl sulfoxide; ester solvents such as γ-butyrolactone, and the like.

[0222] (Other additives)

[0223] Examples of other additives include flame retardants, antioxidants, heat stabilizers, antistatic agents, ultraviolet absorbers, pigments, colorants, lubricants, and the like.

[0224] <Method for producing resin composition>

[0225] The resin composition of the present embodiment can be manufactured by mixing (A) component, (B component, other components used in combination as needed, etc. in a known method. At this time, each component can be dissolved or dispersed while stirring. The conditions such as mixing order, temperature, time, etc. are not particularly limited and can be arbitrarily set according to the type of raw materials, etc.

[0226] <Relative dielectric constant (Dk) of cured product>

[0227] The relative dielectric constant (Dk) of the cured product of the resin composition of the present embodiment at 10 GHz is not particularly limited, but is preferably 3.0 or less, more preferably 2.8 or less, and further preferably 2.7 or less. The smaller the relative dielectric constant (Dk), the more preferred it is. Although its lower limit is not particularly limited, it can be, for example, 2.3 or more, or 2.4 or more, in consideration of the balance with other physical properties.

[0228] The relative dielectric constant (Dk) is a value obtained by a cavity resonator perturbation method, and more specifically, a value measured by the method described in Examples.

[0229] <Dielectric loss tangent of cured product (Df)>

[0230] The dielectric loss tangent (Df) of the cured product of the resin composition of the present embodiment at 10 GHz is not particularly limited, but is preferably 0.0080 or less, more preferably 0.0070 or less, and further preferably 0.0060 or less. The smaller the dielectric loss tangent (Df), the more preferred it is. Although the lower limit is not particularly limited, it may be, for example, 0.0010 or more, or 0.0015 or more, in consideration of the balance with other physical properties.

[0231] The dielectric loss tangent (Df) is a value obtained by a cavity resonator perturbation method, and more specifically, is a value measured by the method described in Examples.

[0232] [Prepreg]

[0233] The prepreg of the present embodiment is a prepreg containing the resin composition of the present embodiment or a semi-cured product of the above-mentioned resin composition.

[0234] The prepreg of the present embodiment is, for example, a prepreg containing the resin composition of the present embodiment or a semi-cured product of the above-mentioned resin composition and a sheet-like fiber base material.

[0235] As the sheet-like fiber base material contained in the prepreg of the present embodiment, for example, a known sheet-like fiber base material that can be used for various laminated plates for electrical insulating materials can be used.

[0236] Examples of the material of the sheet-like 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 sheet-like fiber substrates have shapes such as woven fabrics, nonwoven fabrics, rovings, chopped strand mats, and surface mats.

[0237] The prepreg of the present embodiment can be produced by, for example, impregnating or applying the resin composition of the present embodiment to a sheet-like fiber base material, followed by heating and drying to bring the sheet-like fiber base material into a B-stage.

[0238] The temperature and time of heat drying are not particularly limited, but can be set to, for example, 50 to 200° C. and 1 to 30 minutes from the viewpoint of productivity and appropriately B-stage the resin composition of the present embodiment.

[0239] The solid content concentration of the resin composition in the prepreg of the present embodiment is not particularly limited, but 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 of easily obtaining better formability when forming a laminate.

[0240] [Resin film]

[0241] The resin film of the present embodiment is a resin film containing the resin composition of the present embodiment or a semi-cured product of the above-mentioned resin composition.

[0242] The resin film of the present embodiment can be produced by, for example, applying the resin composition of the present embodiment containing an organic solvent, that is, a resin varnish, to a support and then heating and drying the same.

[0243] Examples of the support include plastic films, metal foils, and release papers.

[0244] The temperature and time of heat drying are not particularly limited, but can be set to 50 to 200° C. and 1 to 30 minutes from the viewpoint of productivity and making the resin composition of the present embodiment appropriately B-staged.

[0245] The resin film of the present embodiment is preferably used to form an insulating layer when a printed wiring board is produced.

[0246] [Laminated board]

[0247] The laminated plate of the present embodiment is a laminated plate including a cured product of the resin composition of the present embodiment and a metal foil.

[0248] In addition, the laminated plate having a metal foil is sometimes also referred to as a metal-clad laminated plate.

[0249] The metal of the metal foil is not particularly limited, and examples thereof include copper, gold, silver, nickel, platinum, molybdenum, ruthenium, aluminum, tungsten, iron, titanium, chromium, and alloys containing one or more of these metal elements.

[0250] The laminated plate of the present embodiment can be produced, for example, by placing a metal foil on one or both surfaces of the prepreg of the present embodiment and then performing heat and pressure molding.

[0251] Usually, the prepreg after B-stage is cured by this heat and pressure molding, thereby obtaining the laminated plate of the present embodiment.

[0252] In the case of heat and pressure molding, only one prepreg may be used, or two or more prepregs may be stacked.

[0253] For the heat and pressure molding, for example, a multi-stage press, a multi-stage vacuum press, a continuous molding machine, an autoclave molding machine, etc. can be used.

[0254] The conditions for the heat-press molding are not particularly limited, and for example, the conditions may be a temperature of 100 to 300° C., a time of 10 to 300 minutes, and a pressure of 1.5 to 5 MPa.

[0255] [Printed circuit board]

[0256] The printed wiring board of the present embodiment is a printed wiring board having a cured product of the resin composition of the present embodiment.

[0257] The printed wiring board of this embodiment can be manufactured by forming a conductor circuit on one or more of the cured product of the prepreg of this embodiment, the cured product of the resin film of this embodiment, and the laminate using a known method. In addition, a multilayer printed wiring board can also be manufactured by further performing a multilayer bonding process as required. The conductor circuit can be formed by appropriately performing a hole opening process, a metal plating process, an etching of a metal foil, etc.

[0258] [Semiconductor package]

[0259] 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.

[0260] The semiconductor package according to the first aspect of the present embodiment can be manufactured by, for example, mounting a semiconductor element, a memory, and the like on a printed wiring board according to the present embodiment using a known method.

[0261] A semiconductor package according to a second aspect of the present embodiment is a semiconductor package including a semiconductor element and a cured product of the resin composition according to the present embodiment that seals the semiconductor element.

[0262] The semiconductor package of the second aspect of the present embodiment can be produced, for example, by a method in which at least a part of a semiconductor element mounted on a printed wiring board is covered with the resin composition of the present embodiment and the resin composition is cured.

[0263] Example

[0264] Hereinafter, the present embodiment will be described in detail with reference to examples, but the present embodiment is not limited to the following examples.

[0265] In addition, in each example, the weight average molecular weight (Mw) and the number average molecular weight (Mn) were measured by the following procedures.

[0266] (Method for measuring weight average molecular weight (Mw) and number average molecular weight (Mn))

[0267] The weight average molecular weight (Mw) and the number average molecular weight (Mn) are converted by gel permeation chromatography (GPC) from a calibration curve using standard polystyrene. The calibration curve is approximated by a cubic formula using standard polystyrene: TSK standard POLYSTYRENE (model: A-2500, A-5000, F-20, F-80) [manufactured by Tosoh Corporation, trade name]. The measurement conditions of GPC are shown below.

[0268] Device: High-speed GPC device HLC-8320GPC

[0269] Detector: UV-8320 ultraviolet absorption detector [manufactured by Tosoh Corporation]

[0270] Column: Guard column: TSK gel guardcolumn Super (HZ)-M + column: TSK gel Super MultiporeHZ-M (2 pieces), Reference column: TSK gel Super H-RC (2 pieces) (both manufactured by Tosoh Corporation, trade names)

[0271] Column size: 4.6×20mm (guard column), 4.6×150mm (column), 6.0×150mm (reference column)

[0272] Eluent: Tetrahydrofuran

[0273] Sample concentration: 10mg / 1mL

[0274] Injection volume: 20μL or 2μL

[0275] Flow rate: 0.35mL / min

[0276] Measurement temperature: 40℃

[0277] [Production of Vinylbenzyl Compounds]

[0278] Production Examples 1 to 3

[0279] (Production of Vinylbenzyl Compounds 1 to 3)

[0280] Into a 500 mL reaction container equipped with a stirrer, a thermometer, a reflux tube and an air pump, the base compound, chloromethylstyrene, a phase transfer catalyst, pure water, a polymerization inhibitor and a solvent in the amounts listed in Table 1 were placed, and the mixture was heated and stirred at 40° C. while blowing air at a flow rate of 50 ml / min.

[0281] Next, while maintaining the temperature at 70°C, the amount of basic compound shown in Table 1 was added dropwise over 20 minutes, and the mixture was stirred at 70°C for 4 hours. It should be noted that air was continuously blown in during the reaction. After cooling to room temperature (25°C) and neutralizing with a 10% aqueous hydrochloric acid solution, the organic layer was washed three times with pure water. Thereafter, the organic layer was precipitated in methanol to obtain the target vinylbenzyl compounds 1 to 3. Vinylbenzyl compounds 1 to 3 were confirmed to have the following structure by infrared absorption (IR) spectral analysis, which is equivalent to component (B1): a structure in which substantially all of the phenolic hydroxyl groups of the base compound are replaced by vinylbenzyl ether groups.

[0282] Production Examples 4 to 5

[0283] (Production of Vinylbenzyl Compounds 4 and 5)

[0284] Into a 500 mL reaction container equipped with a stirrer, a thermometer, a reflux tube and a nitrogen inlet, the base compound, chloromethylstyrene, a phase transfer catalyst, a polymerization inhibitor and a solvent in the amounts listed in Table 1 were placed, and the mixture was heated and stirred at 40° C. while nitrogen was blown in at a flow rate of 50 ml / min.

[0285] Next, the amount of basic compound shown in Table 1 was added dropwise over 20 minutes, and the mixture was stirred at 60°C for 9 hours. It should be noted that nitrogen was continuously blown in during the reaction. After cooling to room temperature (25°C) and neutralizing with a 10% aqueous hydrochloric acid solution, the mixture was washed twice with pure water, toluene was removed by vacuum distillation, and the obtained viscous liquid was washed with methanol, and then vacuum dried to obtain vinylbenzyl compounds 4 and 5. Vinylbenzyl compounds 4 and 5 were obtained by 1 H-NMR analysis confirmed that the compound had the following structure, which was equivalent to component (B2): a structure in which substantially all of the two hydrogen atoms directly bonded to the carbon atom at position 1 of the indene represented by the following formula (B2-3) were replaced by vinylbenzyl groups. In addition, GPC analysis showed that vinylbenzyl compounds 4 and 5 were a mixture of a vinylbenzyl compound having two vinylbenzyl groups introduced and a vinylbenzyl compound having three vinylbenzyl groups introduced.

[0286] [Chemical formula 161

[0287]

[0288] Table 1 shows the weight average molecular weights (Mw) of vinylbenzyl compounds 1 to 5.

[0289] [Table 1]

[0290] Table 1

[0291]

[0292] The details of the compounds described in Table 1 are as follows.

[0293] (Basic Compound)

[0294] ·J-DPP-115: Phenolic resin having a dicyclopentadiene skeleton, manufactured by JFE Chemical Corporation, hydroxyl equivalent 177 to 182 g / eq

[0295] ·MEHC-7851SS: Biphenyl aralkyl phenolic resin, manufactured by Meiwa Chemicals Co., Ltd., weight average molecular weight (Mw) 1,000, number average molecular weight (Mn) 700, hydroxyl equivalent 201 to 220 g / eq

[0296] ·MEHC-7851M: Biphenyl aralkyl phenolic resin, manufactured by Meiwa Chemicals Co., Ltd., weight average molecular weight (Mw) 1,500, number average molecular weight (Mn) 900, hydroxyl equivalent 201 to 220 g / eq

[0297] (Chloromethylstyrene)

[0298] ·CMS: manufactured by Changzhou Wujin Linchuan Chemical Co., Ltd., a mixture of ortho and para forms, ortho form content is 17% by mass, para form content is 83% by mass

[0299] · CMS-P: manufactured by AGC Seimi Chemical Co., Ltd., a mixture of meta-form and para-form, meta-form content 50% by mass, para-form content 50% by mass

[0300] (Phase transfer catalyst)

[0301] ·Tetrabutylphosphonium bromide: manufactured by Kanto Chemical Co., Ltd.

[0302] ·Tetra-n-butylammonium bromide: manufactured by Kanto Chemical Co., Ltd.

[0303] (Basic Compounds)

[0304] Sodium hydroxide: manufactured by Kanto Chemical Co., Ltd., 48 mass % aqueous solution

[0305] [Manufacturing of resin composition]

[0306] Examples 1 to 6, Comparative Examples 1 to 2

[0307] The components listed in Table 2 were mixed in a powder state or mixed with toluene and methyl ethyl ketone in the amounts listed in Table 2, and stirred and mixed at 25° C. to prepare a resin composition having a solid content concentration of about 60% by mass. It should be noted that the unit of the amount of each component in Table 2 is parts by mass, and in the case of a solution, it indicates the parts by mass converted to the solid content.

[0308] The resin composition obtained in each example was applied to a PET film (manufactured by Teijin Co., Ltd., trade name: G2000) with a thickness of 38 μm, and then heated and dried at 140°C for 5 minutes to prepare a resin film in a B-stage state. After the resin film was peeled off from the PET film, it was crushed to obtain a resin powder. Next, the above-mentioned resin powder was put on a Teflon (registered trademark) sheet die-cut to a size of 1 mm thick × 50 mm long × 30 mm wide, and a low-profile copper foil with a thickness of 18 μm (manufactured by Mitsui Mining and Smelting Co., Ltd., trade name: SI-VSP) was arranged on the upper and lower sides thereof in a state where the S surface was in contact with the put-in resin powder. Then, vacuum heating and pressure molding was performed under the conditions of a temperature of 150°C, a pressure of 1.5 to 2.0 MPa, and a time of 120 minutes, and then heating molding was performed under the conditions of a temperature of 180°C and 300 minutes to cure the resin composition. Thereafter, the copper foil on both sides was peeled off to obtain a resin plate (thickness of the resin plate: 1 mm).

[0309] [Evaluation method and measurement method]

[0310] The resin plates obtained in the above-mentioned Examples and Comparative Examples were used to perform various measurements and evaluations according to the following methods.

[0311] (Evaluation of Formability)

[0312] The appearance of the resin plate obtained in each example was visually observed and evaluated based on the following criteria.

[0313] A: The surface of the resin sheet has no gaps and can be cut.

[0314] C: There are gaps on the surface of the resin plate and it cannot be cut.

[0315] (Measurement method of relative dielectric constant (Dk) and dielectric loss tangent (Df))

[0316] The resin plate obtained in each example was cut to make a test piece of 1 mm × 50 mm. Then, based on the cavity resonator perturbation method, the relative dielectric constant (Dk) and dielectric loss tangent (Df) of the above test piece were measured at an atmosphere temperature of 25 ° C and a 10 GHz frequency band. However, the resin composition of Comparative Example 1 has poor formability and cannot make a test piece for measuring the relative dielectric constant (Dk) and dielectric loss tangent (Df), so it is determined to be "unable to measure".

[0317] [Table 2]

[0318] Table 2

[0319]

[0320] It should be noted that the materials in Table 2 are as follows.

[0321] [(A) ingredient]

[0322] Maleimide resin 1: bis(4-maleimidophenyl)methane

[0323] Maleimide resin 2: Aromatic bismaleimide resin containing indane ring

[0324] [(B) ingredient]

[0325] · Vinylbenzyl compounds 1 to 5: Vinylbenzyl compounds 1 to 5 obtained in Production Examples 1 to 5

[0326] From the results shown in Table 2, it can be seen that the resin compositions of Examples 1 to 6 of the present embodiment all have good moldability, low relative dielectric constant (Dk) and dielectric loss tangent (Df), and excellent dielectric properties.

[0327] On the other hand, the resin composition of Comparative Example 1 not containing the component (B) was inferior in moldability. In addition, the resin composition of Comparative Example 2 not containing the component (B) was inferior in dielectric properties.

[0328] In particular, by comparing Examples 2 to 6 and Comparative Example 2, which use the same component (A), it can be seen that the dielectric loss tangent (Df) of the resin compositions of Examples 2 to 6 is significantly reduced compared to the resin composition of Comparative Example 2, and the amount of reduction significantly exceeds the range that can be predicted from the amount of component (B) added.

[0329] Industrial Applicability

[0330] The resin composition of the present embodiment is excellent in dielectric properties, and thus prepregs, laminates, printed wiring boards, semiconductor packages, and the like obtained using the resin composition are particularly suitable for use in electronic components that process high-frequency signals.

Claims

1. A resin composition comprising (A) one or more selected from maleimide resins having one or more N-substituted maleimide groups and derivatives thereof; and (B) a compound having a vinylbenzyl group, The component (B) contains one or more selected from (B1) a compound having three or more vinylbenzyl groups bonded to an oxygen atom, and (B2) a compound having one or more vinylbenzyl groups bonded to a carbon atom.

2. The resin composition according to claim 1, in, The component (B) contains the component (B1), The component (B1) is a compound comprising a structural unit represented by the following general formula (B-1):

3. The resin composition according to claim 1, in, The component (B) contains the component (B2), The component (B2) is a compound including a condensed polycyclic structure including an aromatic ring and a non-aromatic ring.

4. The resin composition according to claim 3, in, The fused polycyclic structure including an aromatic ring and a non-aromatic ring is an indene ring.

5. The resin composition according to any one of claims 1 to 4, in, The component (A) is an aromatic bismaleimide resin having two N-substituted maleimide groups.

6. The resin composition according to any one of claims 1 to 4, in, The content ratio of the N-substituted maleimide group derived from the component (A) to the vinyl group derived from the component (B), that is, N-substituted maleimide group / vinyl group, is 0.05 to 5 on a molar basis. 7 . A prepreg comprising the resin composition according to claim 1 or a semi-cured product of the resin composition. 8 . A laminate comprising a cured product of the resin composition according to claim 1 and a metal foil. 9 . A resin film comprising the resin composition according to claim 1 or a semi-cured product of the resin composition. 10 . A printed wiring board comprising a cured product of the resin composition according to claim 1 .

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 claim 1 that seals the semiconductor element.

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