TW202317678A - Prepreg, laminate and printed wiring board - Google Patents

Abstract

The present invention provides: a prepreg which is capable of reducing skew and transmission loss; a laminate; and a printed wiring board. The present invention provides a prepreg which is obtained by impregnating or coating a glass fiber base material with a resin composition that contains a thermosetting compound, wherein the proportion of the resin composition with respect to the total amount of the prepreg is within the range from 81% by volume to 98% by volume. The skew is able to be reduced by setting the proportion of the resin composition to 81% by volume or more. Meanwhile, if the proportion of the resin composition exceeds 98% by volume, warp after curing becomes large. After the curing, the relative dielectric constant at 10 GHz is 3.3 or less, and the dielectric loss tangent is 0.004 or less.

Description

Prepregs, laminates, and printed wiring boards

The present invention relates to a prepreg, a laminate and a printed wiring board using the prepreg.

In recent years, the speed and capacity of data communication used in information communication have been rapidly developed. Therefore, electronic equipment for information communication requires printed wiring boards corresponding to high frequencies. Insulation materials used in printed wiring boards, for example, prepregs impregnated with glass fiber or coated with resin are widely used. However, since the dielectric properties of glass fiber and resin are different, the delay time (transmission speed) of the signal is deviated due to the density of the glass fiber. As the transmission speed increases, the influence of the propagation delay time difference (SKEW) generated between the differential lines increases, and the SKEW becomes a cause of deterioration of transmission characteristics. In addition, in order to cope with high frequencies, it is also necessary to reduce transmission loss. [Prior Technical Literature] [Patent Document]

[Patent Document 1] International Publication No. 2019/230945

[Technical problem to be solved by the invention]

The present invention is based on such a problem, and an object of the present invention is to provide a prepreg, a laminate, and a printed wiring board. The prepreg system can reduce SKEW and transmission loss.

In addition, Patent Document 1 describes a prepreg for the purpose of reducing variation in delay time of signals. However, in the prepreg described in Patent Document 1, hexagonal boron nitride is interposed between the glass fiber and the conductor wiring, thereby reducing the influence of the high permittivity of the glass fiber on the impedance of the conductor wiring, thereby reducing the SKEW. , its specific composition is different from that of the present invention. [Technical means]

The present invention is as follows. [1] A prepreg impregnated or coated with a resin composition containing a thermosetting compound on a glass fiber substrate, and the ratio of the resin composition to the total amount of the prepreg is 81% by volume or more Within the range of 98 volume % or less, the relative permittivity at 10 GHz after hardening is 3.3 or less, and the dielectric loss tangent is 0.004 or less. [2] The prepreg according to [1], wherein the glass fiber base material is selected from the group consisting of E glass, D glass, S glass, T glass, Q glass, L glass, NE glass, and HME glass At least one type of glass fiber. [3] The prepreg according to [1], wherein the thermosetting compound contains terminal unsaturated group-modified polyphenylene ether. [4] The prepreg according to [3], wherein the content of the terminal unsaturated group-modified polyphenylene ether is 1 to 40 parts by mass relative to 100 parts by mass of resin solids in the resin composition. [5] The prepreg according to [1], wherein the thermosetting compound contains one or more species selected from the group consisting of maleimide compounds, cyanate compounds, epoxy compounds, and phenol compounds. [6] The prepreg according to [1], wherein the resin composition further contains a thermoplastic elastomer. [7] The prepreg according to [6], wherein the content of the thermoplastic elastomer is 1 to 45 parts by mass relative to 100 parts by mass of the resin solid content in the resin composition. [8] The prepreg according to [1], wherein the resin composition further contains a filler. [9] The prepreg according to [8], wherein the content of the filler is 50 to 1600 parts by mass relative to 100 parts by mass of the resin solid content in the resin composition. [10] A laminate comprising a cured product of the prepreg according to any one of [1] to [9]. [11] A printed wiring board having an insulating layer and a conductor layer; the insulating layer is a cured product containing the prepreg according to any one of [1] to [9]. [Effect of the invention]

According to the present invention, SKEW and transmission loss can be reduced. Therefore, it is possible to support high frequencies.

Hereinafter, an embodiment of the present invention (hereinafter referred to as "the present embodiment") will be described in detail, but the present invention is not limited thereto, and various modifications can be made without departing from the gist thereof.

[Prepreg] The prepreg of this embodiment is impregnated or coated with a resin composition containing a thermosetting compound on a glass fiber substrate. The ratio of the resin composition is within the range of 81% by volume to 98% by volume relative to the total amount of the prepreg. The reason is that by setting the ratio of the resin composition to the total amount of the prepreg to be 81% by volume or more, SKEW can be reduced and it is possible to cope with high frequencies. On the other hand, the reason is that if the ratio of the resin composition to the total amount of the prepreg exceeds 98% by volume, the warpage after curing becomes large, and it is not suitable for printed wiring boards. The ratio of the resin composition to the total amount of the prepreg is more preferably 85 volume % or more, and more preferably 86 volume % or more. Furthermore, the ratio of the resin composition to the total amount of the prepreg is more preferably 96% by volume or less, and more preferably 95% by volume or less.

The relative permittivity at 10 GHz after curing of the prepreg is 3.3 or less. The reason is that the lower the relative permittivity, the faster the signal speed can be, and it can correspond to high frequency. It is more preferable that the relative permittivity at 10 GHz after curing of the prepreg is less than 3.2. Also, the lower limit of the relative permittivity at 10 GHz after curing of the prepreg is not particularly limited, and may be, for example, 2.6 or more. In addition, the dielectric loss tangent of the prepreg after hardening at 10 GHz is 0.004 or less. The reason is that the smaller the dielectric loss tangent, the lower the transmission loss can be, and it can correspond to high frequency. The lower limit of the dielectric loss tangent of the prepreg after hardening at 10 GHz is not particularly limited, for example, it may be 0.002 or more.

This prepreg can be semi-hardened (B-staged) by, for example, impregnating or coating a glass fiber substrate with a resin composition, and then drying it at 120-220°C for about 2-15 minutes. get. The ratio of the resin composition to the total amount of the prepreg is the ratio after semi-hardening, and the resin composition also includes the cured product of the resin composition. In addition, as will be described later, the resin composition also contains a filler.

＜Glass fiber substrate＞ The glass fiber substrate, for example, preferably contains at least one glass fiber selected from the group consisting of E glass, D glass, S glass, T glass, Q glass, L glass, NE glass, and HME glass. The form of the fibrous base material is not particularly limited, and examples thereof include woven fabrics, non-woven fabrics, rovings, cut mats, surface mats, and the like. Among them, from the point of view of dimensional stability, woven fabrics that have been treated with ultra-fiber opening and pore blockage are preferred; Coupling agent etc. surface treated woven fabrics are preferred. The thickness of the glass fiber substrate is not particularly limited, for example, it may be 9 μm to 32 μm.

一般式(1)中，X係表示芳基，-(Y-О)n ₂-係表示聚苯醚部分，R ₁、R ₂、R ₃係各自獨立表示氫原子、烷基、烯基或炔基，n ₂係表示1～100之整數，n ₁係表示1～6之整數，n ₃係表示1～4之整數。 <Resin composition> (Terminal unsaturated group-modified polyphenylene ether) The resin composition may contain a terminal unsaturated group-modified polyphenylene ether as a thermosetting compound. The terminal unsaturated group-modified polyphenylene ether is represented by the general formula (1). [chemical 1]

In the general formula (1), X represents an aryl group, -(Y-О)n ₂ - represents a polyphenylene ether moiety, R ₁ , R ₂ , and R ₃ each independently represent a hydrogen atom, an alkyl group, an alkenyl group or In the alkynyl group, n ₂ represents an integer of 1-100, n ₁ represents an integer of 1-6, and n ₃ represents an integer of 1-4.

By containing terminal unsaturated group-modified polyphenylene ether, excellent low permittivity and low dielectric loss tangent properties can be obtained, and in addition, formability can be improved. The terminal unsaturated group-modified polyphenylene ether preferably has a number average molecular weight of not less than 1,000 and not more than 7,000. By setting the number average molecular weight to 7000 or less, fluidity during molding can be ensured. In addition, by setting the number average molecular weight to 1000 or more, excellent dielectric properties (low permittivity, low dielectric loss tangent) and heat resistance of the polyphenylene ether resin itself can be obtained. Wherein, in order to obtain better fluidity, heat resistance, and dielectric properties, the number average molecular weight of the terminal unsaturated group-modified polyphenylene ether may be not less than 1100 and not more than 5000. More preferably, the number average molecular weight of the terminal unsaturated group-modified polyphenylene ether is 4500 or less, and more preferably, the number average molecular weight of the terminal unsaturated group-modified polyphenylene ether is 3000 or less. The number average molecular weight is measured by gel permeation chromatography following established methods.

The terminal unsaturated group-modified polyphenylene ether preferably has a minimum melt viscosity of 50,000 Pa･s or less. By keeping the minimum melt viscosity below 50000Pa･s, fluidity can be ensured and multi-layer molding can be realized. The lower limit of the minimum melt viscosity is not particularly specified, for example, it may be 1000 Pa･s or more.

一般式(2)中，R ₄₀₁、R ₄₀₂、R ₄₀₃、R ₄₀₄係各自獨立地表示碳數6以下之烷基、芳基、鹵素原子、或氫原子。 The terminal unsaturated group-modified polyphenylene ether is preferably a polymer containing a constituent unit represented by the following general formula (2). [Chem 2]

In the general formula (2), R ₄₀₁ , R ₄₀₂ , R ₄₀₃ , and R ₄₀₄ each independently represent an alkyl group having 6 or less carbon atoms, an aryl group, a halogen atom, or a hydrogen atom.

一般式(3)中，R ₄₀₅、R ₄₀₆、R ₄₀₇、R ₄₁₁、R ₄₁₂係各自獨立地表示碳數6以下之烷基或苯基。R ₄₀₈、R ₄₀₉、R ₄₁₀係各自獨立地表示氫原子、碳數6以下之烷基或苯基。 [化4]

一般式(4)中，R ₄₁₃、R ₄₁₄、R ₄₁₅、R ₄₁₆、R ₄₁₇、R ₄₁₈、R ₄₁₉、R ₄₂₀係各自獨立地表示氫原子、碳數6以下之烷基或苯基。-A-為碳數20以下之直鏈狀、支鏈狀或環狀之二價烴基。 與一般式(1)之關係，較佳為上述一般式(2)、(3)、(4)為一般式(1)之-(Y-O)-。-(Y-O)-係具有n ₂之數量（1～100）之重複單元。 The aforementioned polymer may further contain at least one structural unit selected from the group of structural units represented by general formula (3) and general formula (4). [Chem 3]

In the general formula (3), R ₄₀₅ , R ₄₀₆ , R ₄₀₇ , R ₄₁₁ , and R ₄₁₂ each independently represent an alkyl group or phenyl group having 6 or less carbon atoms. R ₄₀₈ , R ₄₀₉ , and R ₄₁₀ each independently represent a hydrogen atom, an alkyl group having 6 or less carbon atoms, or a phenyl group. [chemical 4]

In the general formula (4), R ₄₁₃ , R ₄₁₄ , R ₄₁₅ , R ₄₁₆ , R ₄₁₇ , R ₄₁₈ , R ₄₁₉ , and R ₄₂₀ each independently represent a hydrogen atom, an alkyl group having 6 or less carbon atoms, or a phenyl group. -A- is a linear, branched or cyclic divalent hydrocarbon group having 20 or less carbon atoms. The relationship with the general formula (1) is preferably that the above-mentioned general formulas (2), (3), and (4) are -(YO)- of the general formula (1). -(YO)- is a repeating unit having a number of n ₂ (1-100).

In the general formula (1), X represents an aryl group (aromatic group), -(Y-О)n ₂ - represents a polyphenylene ether moiety, R ₁ , R ₂ , and R ₃ each independently represent a hydrogen atom, an alkane group, alkenyl or alkynyl, n ₂ represents an integer of 1-100, n ₁ represents an integer of 1-6, and n ₃ represents an integer of 1-4. Preferably, n ₁ is an integer ranging from 1 to 4, more preferably n ₁ is 1 or 2, ideally n ₁ is 1. In addition, n ₃ is preferably an integer of 1 to 3, more preferably n ₃ is 1 or 2, ideally n ₃ is 2.

As the aryl group of X in the general formula (1), an aromatic hydrocarbon group can be used. Specifically, a group in which n ₃ hydrogen atoms are removed from a ring structure selected from a benzene ring structure, a biphenyl structure, an indene ring structure, and a naphthalene ring structure (for example, phenyl, biphenyl , indenyl, and naphthyl), preferably biphenyl. Here, the aryl group may also include the above-mentioned aryl group such as a diphenyl ether group bonded with an oxygen atom, or a diphenyl ketone group bonded with a carbonyl group, or a 2,2-diphenyl group bonded through an alkylene group. Phenylpropanyl, etc. In addition, the aryl group may also be substituted by general substituents such as an alkyl group (preferably an alkyl group having 1 to 6 carbon atoms, especially a methyl group), an alkenyl group, an alkynyl group or a halogen atom. However, since the aforementioned "aryl group" is substituted on the polyphenylene ether moiety through an oxygen atom, the limit of the number of substituents generally depends on the number of polyphenylene ether moieties.

一般式(5)中，X為芳基（芳香族基），-(Y-О)n ₂-係個別表示聚苯醚部分，n ₂係個別表示1～100之整數。-(Y-О)n ₂-及n ₂，係與一般式(1)中代表相同意義。亦可包含複數種n ₂不同之化合物。 The terminal unsaturated group-modified polyphenylene ether is particularly preferably a compound represented by a structure represented by the following general formula (5). [chemical 5]

In the general formula (5), X is an aryl group (aromatic group), -(Y-О)n ₂ - represents a polyphenylene ether moiety individually, and n ₂ represents an integer of 1-100 individually. -(Y-О)n ₂ - and n ₂ represent the same meanings as in general formula (1). A plurality of compounds having different n ₂ may also be included.

[化7]

一般式(7)中，R ₄₂₁、R ₄₂₂、R ₄₂₃、R ₄₂₄係各自獨立地表示氫原子或甲基。-B-為碳數20以下之直鏈狀、支鏈狀或環狀之二價烴基。 [化8]

一般式(8)中，-B-為碳數20以下之直鏈狀、支鏈狀或環狀之二價烴基。 [化9]

[化10]

X in general formula (1) and general formula (5) is preferably general formula (6), general formula (7), or general formula (8); general formula (1) and general formula (5) - ( Y-О)n ₂ - is more preferably a structure in which general formula (9) or general formula (10) is arranged, or a structure in which general formula (9) and general formula (10) are randomly arranged. [chemical 6]

[chemical 7]

In the general formula (7), R ₄₂₁ , R ₄₂₂ , R ₄₂₃ , and R ₄₂₄ each independently represent a hydrogen atom or a methyl group. -B- is a linear, branched or cyclic divalent hydrocarbon group having 20 or less carbon atoms. [chemical 8]

In the general formula (8), -B- is a linear, branched or cyclic divalent hydrocarbon group having 20 or less carbon atoms. [chemical 9]

[chemical 10]

There is no particular limitation on the production method of terminal unsaturated group-modified polyphenylene ether having a structure represented by general formula (5). For example, bifunctional phenolic compound and monofunctional phenolic compound can be obtained by oxidative coupling The terminal phenolic hydroxyl group of the phenylene ether oligomer is produced by performing vinylbenzyl etherification. In addition, such a terminal unsaturated group-modified polyphenylene ether can use a commercial item, for example, OPE-2St1200 and OPE-2st2200 by Mitsubishi Gas Chemical Co., Ltd. can be used suitably.

The content of the terminal unsaturated group-modified polyphenylene ether in the resin composition, when contained, is preferably at least 1 part by mass, more preferably at least 5 parts by mass, based on 100 parts by mass of the resin solid content of the resin composition , and more preferably at least 10 parts by mass, further preferably at least 15 parts by mass, and still more preferably at least 20 parts by mass. In addition, the upper limit of the content is preferably 70 parts by mass or less, more preferably 65 parts by mass or less, and may be 60 parts by mass or less. By falling within such a range, low permittivity, low dielectric loss tangent, and good formability tend to be effectively achieved. The resin composition may contain only one type of terminal unsaturated group-modified polyphenylene ether, or may contain two or more types. When two or more kinds are included, the total amount is preferably within the above-mentioned range.

In addition, the "resin solid content in the resin composition" in the present invention refers to the resin composition in which fillers, hardening accelerators, and additives have been removed, unless otherwise specified, and the resin solid content is 100 parts by mass. , means that the total amount of components in the resin composition excluding fillers, hardening accelerators, and additives is 100 parts by mass.

(maleimide compound) The resin composition may contain a maleimide compound as a thermosetting compound. Maleimide compounds, as long as they have one or more (preferably 2 to 12, more preferably 2 to 6, more preferably 2 to 4, still more preferably 2 or 3 in the molecule, still more preferably The maleimide-based compound of 2) is preferable, and is not particularly limited. Specific examples thereof include N-phenylmaleimide, N-hydroxyphenylmaleimide, bis(4-maleimidephenyl)methane, 4,4'-diphenyl Methyl methane bismaleimide, bis(3,5-dimethyl-4-maleimidephenyl)methane, bis(3,5-diethyl-4-maleimidephenyl) ) methane, phenylmethanemaleimide, o-phthalamide maleimide, m-phthalamide maleimide, terephthalamide Citraconimide, terephthalimide, 2,2-bis(4-(4-maleimidephenoxy)-phenyl)propane, 3,3'-diethyl- 5,5'-Dimethyl-4,4'-diphenylmethane bismaleimide, 4-methyl-1,3-phenylene bismaleimide, 1,6-bismaleimide Laimide-(2,2,4-trimethyl)hexane, 4,4'-diphenyl ether bismaleimide, 4,4'-diphenylene bismaleimide, 1 ,3-bis(3-maleimidephenoxy)benzene, 1,3-bis(4-maleimidephenoxy)benzene, 4,4'-diphenylmethane biscitraconyl imine, 2,2-bis[4-(4-citraconimidephenoxy)phenyl]propane, bis(3,5-dimethyl-4-citraconimidephenyl)methane, Bis(3-ethyl-5-methyl-4-citraconamide phenyl)methane, bis(3,5-diethyl-4-citraconamide phenyl)methane, in the general formula ( 11), maleimide compounds represented by general formula (12), general formula (13), general formula (14), general formula (15), and general formula (16), etc.

一般式(11)中，R ₅₁、R ₅₂係各自獨立地表示氫原子或甲基，較佳為氫原子。此外，一般式(11)中，n ₄係表示1以上之整數，n ₄之上限值通常為10，從對有機溶劑之溶解性之觀點而言，n ₄之上限值較佳為7，更佳為5。一般式(11)所表示之化合物，亦可包含n ₄為不同之2種以上之化合物。 [chemical 11]

In the general formula (11), R ₅₁ and R ₅₂ each independently represent a hydrogen atom or a methyl group, preferably a hydrogen atom. In addition, in the general formula (11), n ₄ represents an integer of 1 or more, and the upper limit of n ₄ is usually 10, and from the viewpoint of solubility in organic solvents, the upper limit of n ₄ is preferably 7 , more preferably 5. The compound represented by the general formula (11) may include two or more compounds in which n ₄ is different.

一般式(12)中，R ₆₀₁、R ₆₀₂、R ₆₀₃、R ₆₀₄、R ₆₀₅、R ₆₀₆、R ₆₀₇、R ₆₀₈、R ₆₀₉、R ₆₁₀、R ₆₁₁、R ₆₁₂係各自獨立地表示氫原子、碳數1～8之烷基（例如，甲基、乙基、正丙基、異丙基、正丁基、異丁基、三級丁基、正戊基等）、或苯基。此等之中，較佳為選自氫原子、甲基、及苯基所成群之基團，更佳為氫原子及甲基中之一者，又更佳為氫原子。 此外，一般式(12)中，n ₅為1≦n ₅≦10之整數。從溶劑溶解性進一步更優良之觀點而言，n ₅較佳為4以下，更佳為3以下，又更佳為2以下。一般式(12)所表示之化合物，亦可包含n ₅為不同之2種以上之化合物。 [chemical 12]

In the general formula (12), R ₆₀₁ , R ₆₀₂ , R ₆₀₃ , R ₆₀₄ , R ₆₀₅ , R ₆₀₆ , R ₆₀₇ , R ₆₀₈ , R ₆₀₉ , R ₆₁₀ , R ₆₁₁ , and R ₆₁₂ each independently represent a hydrogen atom, Alkyl having 1 to 8 carbons (for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tertiary butyl, n-pentyl, etc.), or phenyl. Among them, a group selected from a hydrogen atom, a methyl group, and a phenyl group is preferable, one of a hydrogen atom and a methyl group is more preferable, and a hydrogen atom is still more preferable. In addition, in general formula (12), n ₅ is an integer of 1≦n ₅ ≦10. From the viewpoint of further excellent solvent solubility, n ₅ is preferably 4 or less, more preferably 3 or less, still more preferably 2 or less. The compound represented by the general formula (12) may include two or more compounds in which n ₅ is different.

一般式(13)中，R ₇₁、R ₇₂、R ₇₃、R ₇₄係各自獨立地表示氫原子、甲基或乙基，R ₈₁、R ₈₂係各自獨立地表示氫原子或甲基。從低電容率性及低介電損耗角正切性進一步更優良之觀點而言，R ₇₁、R ₇₂、R ₇₃、R ₇₄較佳為甲基或乙基。如此之化合物，例如，可列舉3,3'-二乙基-5,5'-二甲基-4,4'-二苯基甲烷雙馬來醯亞胺。 [chemical 13]

In the general formula (13), R ₇₁ , R ₇₂ , R ₇₃ , and R ₇₄ each independently represent a hydrogen atom, a methyl group or an ethyl group, and R ₈₁ and R ₈₂ each independently represent a hydrogen atom or a methyl group. R ₇₁ , R ₇₂ , R ₇₃ , and R ₇₄ are preferably methyl groups or ethyl groups from the viewpoint of further excellent low permittivity and low dielectric loss tangent properties. Such a compound includes, for example, 3,3'-diethyl-5,5'-dimethyl-4,4'-diphenylmethanebismaleimide.

一般式(14)中，R ₉₁、R ₉₂係各自獨立地表示氫原子、甲基或乙基。從低電容率性及低介電損耗角正切性進一步更優良之觀點而言，R ₉₁、R ₉₂較佳為甲基。如此之化合物，例如，可列舉2,2-雙(4-(4-馬來醯亞胺苯氧基)-苯基)丙烷。 [chemical 14]

In the general formula (14), R ₉₁ and R ₉₂ each independently represent a hydrogen atom, a methyl group or an ethyl group. R ₉₁ and R ₉₂ are preferably methyl groups from the standpoint of further excellent low permittivity and low dielectric loss tangent properties. Such a compound includes, for example, 2,2-bis(4-(4-maleimidophenoxy)-phenyl)propane.

一般式(15)中，n ₆係表示1以上之整數。一般式(15)所表示之化合物，亦可包含n ₆為不同之2種以上之化合物。 [chemical 15]

In the general formula (15), n ₆ represents an integer of 1 or more. The compound represented by the general formula (15) may include two or more compounds in which n ₆ is different.

一般式(16)中，R ^M1、R ^M2、R ^M3、及R ^M4係個別獨立地表示氫原子或有機基。R ^M5及R ^M6係個別獨立地表示氫原子或烷基。Ar ^M係表示二價之芳香族基。A係4～6元環之脂環基。R ^M7及R ^M8係個別獨立地為烷基。mx係1或2，lx係0或1。R ^M9及R ^M10係個別獨立地表示氫原子或烷基。R ^M11、R ^M12、R ^M13、及R ^M14係個別獨立地表示氫原子或有機基。nx係表示1以上20以下之整數。一般式(16)所表示之化合物，亦可包含nx為不同之2種以上之化合物。 [chemical 16]

In general formula (16), R ^M1 , R ^M2 , R ^M3 , and R ^M4 each independently represent a hydrogen atom or an organic group. R ^M5 and R ^M6 each independently represent a hydrogen atom or an alkyl group. Ar ^M represents a divalent aromatic group. A is an alicyclic group with 4-6 membered rings. R ^M7 and R ^M8 are each independently an alkyl group. mx is 1 or 2, lx is 0 or 1. R ^M9 and R ^M10 each independently represent a hydrogen atom or an alkyl group. R ^M11 , R ^M12 , R ^M13 , and R ^M14 each independently represent a hydrogen atom or an organic group. nx represents an integer ranging from 1 to 20. The compound represented by the general formula (16) may include two or more compounds in which nx is different.

R ^M1 , R ^M2 , R ^M3 , and R ^M4 in the general formula (16) each independently represent a hydrogen atom or an organic group. The organic group here is preferably an alkyl group, more preferably an alkyl group having 1 to 12 carbons, more preferably an alkyl group having 1 to 6 carbons, and more preferably methyl, ethyl, propyl, or butyl. group, particularly preferably methyl. R ^M1 and R ^M3 are each independently preferably an alkyl group, and R ^M2 and R ^M4 are preferably a hydrogen atom. R ^M5 and R ^M6 each independently represent a hydrogen atom or an alkyl group, preferably an alkyl group. The alkyl group here is preferably an alkyl group having 1 to 12 carbons, more preferably an alkyl group having 1 to 6 carbons, and more preferably methyl, ethyl, propyl, or butyl, and particularly preferably methyl. Ar ^M represents a divalent aromatic group, preferably a phenylene group, a naphthalene diyl group, a phenanthrene diyl group, and an anthracenediyl group, more preferably a phenylene group, and even more preferably a m-phenylene group. Ar ^M may also have a substituent, and the substituent is preferably an alkyl group, more preferably an alkyl group with 1 to 12 carbons, more preferably an alkyl group with 1 to 6 carbons, and more preferably a methyl group or an ethyl group , propyl, butyl, particularly preferably methyl. Among them, Ar ^M is preferably unsubstituted. A is a 4-6 membered alicyclic group, more preferably a 5-membered alicyclic group (preferably a group combined with a benzene ring to form an indane ring). R ^M7 and R ^M8 are each independently an alkyl group, preferably an alkyl group having 1 to 6 carbon atoms, more preferably an alkyl group having 1 to 3 carbon atoms, particularly preferably a methyl group. mx is 1 or 2, preferably 2. lx is 0 or 1, preferably 1. R ^M9 and R ^M10 each independently represent a hydrogen atom or an alkyl group, preferably an alkyl group. The alkyl group here is preferably an alkyl group having 1 to 12 carbons, more preferably an alkyl group having 1 to 6 carbons, and more preferably methyl, ethyl, propyl, or butyl, and particularly preferably methyl. R ^M11 , R ^M12 , R ^M13 and R ^M14 each independently represent a hydrogen atom or an organic group. The organic group here is preferably an alkyl group, more preferably an alkyl group having 1 to 12 carbons, more preferably an alkyl group having 1 to 6 carbons, and more preferably methyl, ethyl, propyl, or butyl. group, particularly preferably methyl. R ^M12 and R ^M13 are each independently preferably an alkyl group, and R ^M11 and R ^M14 are preferably a hydrogen atom. nx represents an integer ranging from 1 to 20.

一般式(17)中，R ^M21、R ^M22、R ^M23、及R ^M24係個別獨立地表示氫原子或有機基。R ^M25及R ^M26係個別獨立地表示氫原子或烷基。R ^M27、R ^M28、R ^M29、及R ^M30係個別獨立地表示氫原子或有機基。R ^M31及R ^M32係個別獨立地表示氫原子或烷基。R ^M33、R ^M34、R ^M35、及R ^M36係個別獨立地表示氫原子或有機基。R ^M37、R ^M38、R ^M39係個別獨立地表示氫原子或烷基。nx係表示1以上20以下之整數。 The compound represented by the general formula (16) is preferably a compound represented by the following general formula (17). [chemical 17]

In the general formula (17), R ^M21 , R ^M22 , R ^M23 , and R ^M24 each independently represent a hydrogen atom or an organic group. R ^M25 and R ^M26 each independently represent a hydrogen atom or an alkyl group. R ^M27 , R ^M28 , R ^M29 , and R ^M30 each independently represent a hydrogen atom or an organic group. R ^M31 and R ^M32 each independently represent a hydrogen atom or an alkyl group. R ^M33 , R ^M34 , R ^M35 , and R ^M36 each independently represent a hydrogen atom or an organic group. R ^M37 , R ^M38 , and R ^M39 each independently represent a hydrogen atom or an alkyl group. nx represents an integer ranging from 1 to 20.

In general formula (17), R ^M21 , R ^M22 , R ^M23 and R ^M24 each independently represent a hydrogen atom or an organic group. The organic group here is preferably an alkyl group, more preferably an alkyl group having 1 to 12 carbons, more preferably an alkyl group having 1 to 6 carbons, and more preferably methyl, ethyl, propyl, or butyl. group, particularly preferably methyl. R ^M21 and R ^M23 are preferably alkyl groups, and R ^M22 and R ^M24 are preferably hydrogen atoms. R ^M25 and R ^M26 each independently represent a hydrogen atom or an alkyl group, preferably an alkyl group. The alkyl group here is preferably an alkyl group having 1 to 12 carbons, more preferably an alkyl group having 1 to 6 carbons, and more preferably methyl, ethyl, propyl, or butyl, and particularly preferably methyl. R ^M27 , R ^M28 , R ^M29 and R ^M30 each independently represent a hydrogen atom or an organic group, preferably a hydrogen atom. The organic group here is preferably an alkyl group, more preferably an alkyl group having 1 to 12 carbons, more preferably an alkyl group having 1 to 6 carbons, and more preferably methyl, ethyl, propyl, or butyl. group, particularly preferably methyl. R ^M31 and R ^M32 each independently represent a hydrogen atom or an alkyl group, preferably an alkyl group. The alkyl group here is preferably an alkyl group having 1 to 12 carbons, more preferably an alkyl group having 1 to 6 carbons, and more preferably methyl, ethyl, propyl, or butyl, and particularly preferably methyl. R ^M33 , R ^M34 , R ^M35 and R ^M36 each independently represent a hydrogen atom or an organic group. The organic group here is preferably an alkyl group, more preferably an alkyl group having 1 to 12 carbons, more preferably an alkyl group having 1 to 6 carbons, and more preferably methyl, ethyl, propyl, or butyl. group, particularly preferably methyl. R ^M33 and R ^M36 are preferably hydrogen atoms, and R ^M34 and R ^M35 are preferably alkyl groups. R ^M37 , R ^M38 , and R ^M39 each independently represent a hydrogen atom or an alkyl group, preferably an alkyl group. The alkyl group here is preferably an alkyl group having 1 to 12 carbons, more preferably an alkyl group having 1 to 6 carbons, and more preferably methyl, ethyl, propyl, or butyl, and particularly preferably methyl. nx represents an integer ranging from 1 to 20.

一般式(18)中，nx係表示1以上20以下之整數。 The compound represented by the general formula (17) is preferably a compound of the following general formula (18). [chemical 18]

In the general formula (18), nx represents an integer of 1 to 20.

The molecular weight of the compound represented by the general formula (16) is preferably at least 500, more preferably at least 600, and still more preferably at least 700. There exists a tendency for a dielectric characteristic and low water absorption to be improved more by making molecular weight more than the said lower limit. In addition, the molecular weight of the compound represented by general formula (16) is preferably 10000 or less, more preferably 9000 or less, still more preferably 7000 or less, still more preferably 5000 or less, still more preferably 4000 or less. There exists a tendency for heat resistance and handleability to be improved more by making molecular weight below the said upper limit.

Among them, the maleimide compound preferably includes at least one compound represented by general formulas (11), (12), (13), (14), (15) and (16). The reason is that low thermal expansion and heat resistance can be improved. Commercially available maleimide compounds can also be used. For example, the maleimide compound represented by the general formula (11) can suitably use "BMI-2300" manufactured by Daiwa Chemical Industry Co., Ltd., and the general formula (12) The maleimide compound represented can suitably use "MIR-3000" manufactured by Nippon Kayaku Co., Ltd., and the maleimide compound represented by the general formula (13) can suitably use K･I Kasei Co., Ltd. "BMI-70", the maleimide compound represented by the general formula (14), can suitably use the maleimide compound represented by the general formula (15) "BMI-80" manufactured by K･I Chemical Co., Ltd. The compound can suitably use "MIR-5000" manufactured by Nippon Kayaku Co., Ltd., and the maleimide compound represented by the general formula (16) can suitably use "X9-450" and "X9-470" manufactured by DIC Corporation. "NE-X-9470S".

The content of the maleimide compound in the resin composition can be appropriately set in accordance with desired properties, and is not particularly limited. When contained, the content of the maleimide compound is preferably at least 1 part by mass, more preferably at least 5 parts by mass, and still more preferably at least 100 parts by mass of the resin solid content in the resin composition. More than 10 parts by mass. The upper limit is preferably at most 90 parts by mass, more preferably at most 60 parts by mass, still more preferably at most 50 parts by mass, and may be at most 40 parts by mass. By falling within such a range, high heat resistance and low water absorption tend to be more effectively exhibited. Maleimide compounds may be used alone or in combination of two or more. In the case of using two or more kinds, the total amount is preferably within the above-mentioned range.

(cyanate compound) The resin composition may contain a cyanate compound as a thermosetting compound. Cyanate compounds, as long as they have one or more (preferably 2 to 12, more preferably 2 to 6, more preferably 2 to 4, still more preferably 2 or 3, and more preferably 2 or 3 in the molecule) More preferably, the resin having an aromatic moiety substituted with a cyanoxy group (cyanate group) in 2) is not particularly limited. As a cyanate compound, the compound represented by general formula (19) is mentioned, for example.

一般式(19)中，Ar ₁、Ar ₂係各自獨立地表示可具有取代基之伸苯基、可具有取代基之伸萘基或可具有取代基之聯伸苯基。R ₁₀₁、R ₁₀₂係各自獨立地選自氫原子、可具有取代基之碳數1～6之烷基、可具有取代基之碳數6～12之芳基、可具有取代基之碳數1～4之烷氧基、可具有與碳數1～6之烷基及碳數6～12之芳基鍵結之取代基之芳烷基、或可具有與碳數1～6之烷基及碳數6～12之芳基鍵結之取代基之烷芳基中之任一種。n ₇₁係表示鍵結於Ar ₁之氰氧基之數量，且為1～3之整數。n ₇₂係表示鍵結於Ar ₂之氰氧基之數量，且為1～3之整數。 n ₇₃係表示鍵結於Ar ₁之R ₁₀₁之數量，Ar ₁為伸苯基時係4-n ₇₁、為伸萘基時係6-n ₇₁、為聯伸苯基時係8-n ₇₁。n ₇₄係表示鍵結於Ar ₂之R ₁₀₂之數量，Ar ₂為伸苯基時係4-n ₇₂、為伸萘基時係6-n ₇₂、為聯伸苯基時係8-n ₇₂。n ₈係表示平均重複數量，且為0～50之整數。氰酸酯化合物，亦可為n ₈不同之化合物之混合物。Z係各自獨立地選自單鍵、碳數1～50之二價之有機基（氫原子亦可被雜原子取代）、氮數1～10之二價之有機基（-N-R-N-等）、羰基（-CO-）、羧基（-C(=O)O-）、二氧化羰基（-OC(=O)O-）、磺醯基（-SO ₂-）、及二價之硫原子或二價之氧原子中之任一種。 [chemical 19]

In the general formula (19), Ar ₁ and Ar ₂ each independently represent a phenylene group which may have a substituent, a naphthylene group which may have a substituent, or a biphenylene group which may have a substituent. R ₁₀₁ and R ₁₀₂ are each independently selected from a hydrogen atom, an alkyl group with 1 to 6 carbon atoms that may have a substituent, an aryl group with 6 to 12 carbon atoms that may have a substituent, and an aryl group with 1 to 2 carbon atoms that may have a substituent. An alkoxy group with ∼4, an aralkyl group that may have a substituent bonded to an alkyl group with 1 to 6 carbons and an aryl group with 6 to 12 carbons, or an aralkyl group that may have an alkyl group with 1 to 6 carbons and an aryl group with 6 to 12 carbons Any of the alkaryl groups of substituents bonded to an aryl group having 6 to 12 carbon atoms. n ₇₁ represents the number of cyanoxy groups bonded to Ar ₁ and is an integer of 1-3. n ₇₂ represents the number of cyanoxy groups bonded to Ar ₂ and is an integer of 1-3. n ₇₃ represents the number of R ₁₀₁ bonded to Ar ₁ , when Ar ₁ is phenylene, it is 4-n ₇₁ , when it is naphthylylene, it is 6-n ₇₁ , when it is biphenylene, it is 8-n ₇₁ . n ₇₄ represents the number of R ₁₀₂ bonded to Ar ₂ , Ar ₂ is 4-n ₇₂ when it is phenylene, 6-n ₇₂ when it is naphthyl, and 8-n ₇₂ when it is biphenylene . n ₈ represents the average number of repetitions, and is an integer of 0-50. The cyanate compound may also be a mixture of n ₈ different compounds. Z is each independently selected from a single bond, a divalent organic group with 1 to 50 carbons (hydrogen atoms can also be replaced by heteroatoms), a divalent organic group with 1 to 10 nitrogens (-NRN-, etc.), Carbonyl (-CO-), carboxyl (-C(=O)O-), carbonyl dioxide (-OC(=O)O-), sulfonyl (-SO ₂ -), and divalent sulfur atoms or Any of divalent oxygen atoms.

The alkyl group of R ₁₀₁ and R ₁₀₂ in general formula (19) may have a linear structure, a branched structure, or a cyclic structure (cycloalkyl, etc.). In addition, the hydrogen atoms in the alkyl groups of general formula (19) and the aryl groups of R ₁₀₁ and R ₁₀₂ can also pass through halogen atoms such as fluorine atoms and chlorine atoms; alkoxy groups such as methoxy and phenoxy; Cyano and other substitutions. Specific examples of the alkyl group include methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tertiary butyl, n-pentyl, 1-ethylpropyl, 2,2-di Methylpropyl, cyclopentyl, hexyl, cyclohexyl, trifluoromethyl, etc. Specific examples of the aryl group include phenyl, xylyl, 2,4,6-trimethylphenyl (mesityl), naphthyl, phenoxyphenyl, ethylphenyl, o-fluorophenyl, m-fluorobenzene base, p-fluorophenyl, dichlorophenyl, dicyanophenyl, trifluorophenyl, methoxyphenyl, o-tolyl, m-tolyl, p-tolyl, etc. Specific examples of the alkoxy group include methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy and the like.

Specific examples of the divalent organic group of Z in the general formula (19) include methylene, ethylene, trimethylene, cyclopentyl, cyclohexyl, trimethylcyclohexyl, biphenylene Methyl, dimethylmethylene-phenylene-dimethylmethylene, fluorene diyl, phthalidediyl, etc. The hydrogen atom in the divalent organic group may also be substituted by a halogen atom such as a fluorine atom or a chlorine atom; an alkoxy group such as a methoxy group or a phenoxy group; or a cyano group. The divalent organic group having 1 to 10 nitrogens in Z in the general formula (19) includes an imine group, a polyimide group, and the like.

In addition, Z in the general formula (19) may include a structure represented by the general formula (20) or the general formula (21).

一般式(20)中，Ar ₃係選自伸苯基、伸萘基、及聯伸苯基之任一種。R ₁₀₃、R ₁₀₄、R ₁₀₇、R ₁₀₈係各自獨立地選自氫原子、碳數1～6之烷基、碳數6～12之芳基、以及經三氟甲基及酚性羥基之至少一個取代之芳基中之任一種。R ₁₀₅、R ₁₀₆係各自獨立地選自氫原子、碳數1～6之烷基、碳數6～12之芳基、碳數1～4之烷氧基及羥基之任一種。n ₉係表示0～5之整數，惟氰酸酯化合物，亦可為具有n ₉為不同之基團之化合物之混合物。 [chemical 20]

In the general formula (20), Ar ₃ is any one selected from phenylene, naphthylene, and biphenylene. R ₁₀₃ , R ₁₀₄ , R ₁₀₇ , and R ₁₀₈ are each independently selected from a hydrogen atom, an alkyl group with 1 to 6 carbons, an aryl group with 6 to 12 carbons, and at least Any of a substituted aryl group. R ₁₀₅ and R ₁₀₆ are each independently selected from a hydrogen atom, an alkyl group having 1 to 6 carbons, an aryl group having 6 to 12 carbons, an alkoxy group having 1 to 4 carbons, and a hydroxyl group. n ₉ represents an integer of 0 to 5, but the cyanate compound may also be a mixture of compounds having n ₉ different groups.

一般式(21)中，Ar ₄係選自伸苯基、伸萘基或聯伸苯基之任一種。R ₁₀₉、R ₁₁₀係各自獨立地選自氫原子、碳數1～6之烷基、碳數6～12之芳基、苄基、碳數1～4之烷氧基、以及經羥基、三氟甲基及氰氧基之至少一個取代之芳基中之任一種。n ₁₀係表示0～5之整數，惟氰酸酯化合物，亦可為具有n ₁₀為不同之基團之化合物之混合物。 [chem 21]

In the general formula (21), Ar ₄ is selected from any one of phenylene, naphthylene or biphenylene. R ₁₀₉ and R ₁₁₀ are each independently selected from a hydrogen atom, an alkyl group with 1 to 6 carbons, an aryl group with 6 to 12 carbons, a benzyl group, an alkoxy group with 1 to 4 carbons, and a hydroxyl, tri Any one of at least one substituted aryl group of fluoromethyl group and cyanooxy group. n ₁₀ represents an integer of 0 to 5, but the cyanate compound may also be a mixture of compounds having n ₁₀ as different groups.

Furthermore, Z in the general formula (19) includes a divalent group represented by the following formula.

式中，n ₁₁係表示4～7之整數。R ₁₁₁、R ₁₁₂係各自獨立地表示氫原子或碳數1～6之烷基。 [chem 22]

In the formula, _n11 represents an integer of 4-7. R ₁₁₁ and R ₁₁₂ each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbons.

Specific examples of Ar ₃ in general formula (20) and Ar ₄ in general formula (21) include 1,4-phenylene, 1,3-phenylene, 4,4'-biphenylene, 2 ,4'-biphenylene, 2,2'-biphenylene, 2,3'-biphenylene, 3,3'-biphenylene, 3,4'-biphenylene, 2 ,6-naphthyl, 1,5-naphthyl, 1,6-naphthyl, 1,8-naphthyl, 1,3-naphthyl, 1,4-naphthyl, etc. The alkyl and aryl groups in R ₁₀₃ to R ₁₀₈ in general formula (20) and R ₁₀₉ and R ₁₁₀ in general formula (21) are the same as those described in general formula (19).

The cyanate compound represented by the general formula (19) includes, for example, phenol novolac type cyanate compound, naphthol aralkyl type cyanate compound, biphenyl aralkyl type cyanate compound, naphthyl ether Type cyanate compound, xylene resin type cyanate compound, adamantane skeleton type cyanate compound, bisphenol A type cyanate compound, diallyl bisphenol A type cyanate compound, naphthol arane Cyanate compounds, etc.

Specific examples of the cyanate compound represented by the general formula (19) include: cyanooxybenzene, 1-cyanooxy-2-methylbenzene, 1-cyanooxy-3-methylbenzene, 1-cyanooxybenzene, Cyanooxy-4-methylbenzene, 1-cyanooxy-2-methoxybenzene, 1-cyanooxy-3-methoxybenzene, 1-cyanooxy-4-methoxybenzene, 1 -cyanooxy-2,3-dimethylbenzene, 1-cyanooxy-2,4-dimethylbenzene, 1-cyanooxy-2,5-dimethylbenzene, 1-cyanooxy- 2,6-Dimethylbenzene, 1-cyanooxy-3,4-dimethylbenzene, 1-cyanooxy-3,5-dimethylbenzene, cyanooxyethylbenzene, cyanooxybutyl phenylbenzene, cyanooxyoctylbenzene, cyanoxynonylbenzene, 2-(4-cyanophenyl)-2-phenylpropane (cyanate ester of 4-α-cumylphenol), 1-cyanooxy -4-cyclohexylbenzene, 1-cyanooxy-4-vinylbenzene, 1-cyanooxy-2-chlorobenzene, 1-cyanooxy-3-chlorobenzene, 1-cyanooxy-2,6 -Dichlorobenzene, 1-cyanooxy-2-methyl-3-chlorobenzene, cyanooxynitrobenzene, 1-cyanooxy-4-nitro-2-ethylbenzene, 1-cyanooxy -2-Methoxy-4-allylbenzene (cyanate ester of eugenol), methyl(4-cyanooxyphenyl) sulfide, 1-cyanooxy-3-trifluoromethylbenzene, 4-Cyanooxybiphenyl, 1-Cyanooxy-2-Acetylbenzene, 1-Cyanooxy-4-Acetylbenzene, 4-Cyanooxybenzaldehyde, Methyl 4-Cyanooxybenzoate, Phenyl 4-cyanooxybenzoate, 1-cyanooxy-4-acetamidobenzene, 4-cyanooxybenzophenone, 1-cyanooxy-2,6-di-tert-butyl Benzene, 1,2-dicyanoxybenzene, 1,3-dicyanoxybenzene, 1,4-dicyanoxybenzene, 1,4-dicyanoxy-2-tertiary butylbenzene, 1 ,4-Dicyanooxy-2,4-dimethylbenzene, 1,4-dicyanooxy-2,3,4-trimethylbenzene, 1,3-dicyanooxy-2,4, 6-trimethylbenzene, 1,3-dicyanooxy-5-toluene, 1-cyanooxynaphthalene, 2-cyanooxynaphthalene, 1-cyanooxy-4-methoxynaphthalene, 2-cyano Oxy-6-methylnaphthalene, 2-cyanooxy-7-methoxynaphthalene, 2,2'-dicyanooxy-1,1'-binaphthalene, 1,3-dicyanooxynaphthalene, 1,4-Dicyanoxynaphthalene, 1,5-Dicyanoxynaphthalene, 1,6-Dicyanoxynaphthalene, 1,7-Dicyanoxynaphthalene, 2,3-Dicyanoxynaphthalene, 2,6-dicyanoxynaphthalene, 2,7-dicyanoxynaphthalene, 2,2'-dicyanoxybiphenyl, 4,4'-dicyanoxybiphenyl, 4,4'-bis Cyanooxyoctafluorobiphenyl, 2,4'-dicyanoxydiphenylmethane, 4,4'-dicyanoxydiphenylmethane, bis(4-cyanooxy-3,5-dimethylbenzene ) methane, 1,1-bis(4-cyanooxyphenyl)ethane, 1,1-bis(4-cyanooxyphenyl)propane, 2,2-bis(4-cyanooxyphenyl) Propane, 2,2-bis(3-allyl-4-cyanooxyphenyl)propane, 2,2-bis(4-cyanooxy-3-methylphenyl)propane, 2,2-bis (2-cyanooxy-5-biphenyl)propane, 2,2-bis(4-cyanooxyphenyl)hexafluoropropane, 2,2-bis(4-cyanooxy-3,5-bis Methylphenyl)propane, 1,1-bis(4-cyanooxyphenyl)butane, 1,1-bis(4-cyanooxyphenyl)isobutane, 1,1-bis(4- Cyanooxyphenyl)pentane, 1,1-bis(4-cyanoxyphenyl)-3-methylbutane, 1,1-bis(4-cyanoxyphenyl)-2-methyl Butane, 1,1-bis(4-cyanophenyl)-2,2-dimethylpropane, 2,2-bis(4-cyanophenyl)butane, 2,2-bis( 4-cyanooxyphenyl) pentane, 2,2-bis(4-cyanooxyphenyl)hexane, 2,2-bis(4-cyanooxyphenyl)-3-methylbutane, 2,2-bis(4-cyanooxyphenyl)-4-methylpentane, 2,2-bis(4-cyanooxyphenyl)-3,3-dimethylbutane, 3,3 -bis(4-cyanooxyphenyl)hexane, 3,3-bis(4-cyanooxyphenyl)heptane, 3,3-bis(4-cyanooxyphenyl)octane, 3, 3-bis(4-cyanooxyphenyl)-2-methylpentane, 3,3-bis(4-cyanooxyphenyl)-2-methylhexane, 3,3-bis(4- cyanooxyphenyl)-2,2-dimethylpentane, 4,4-bis(4-cyanooxyphenyl)-3-methylheptane, 3,3-bis(4-cyanooxy Phenyl)-2-methylheptane, 3,3-bis(4-cyanooxyphenyl)-2,2-dimethylhexane, 3,3-bis(4-cyanooxyphenyl) -2,4-Dimethylhexane, 3,3-bis(4-cyanooxyphenyl)-2,2,4-trimethylpentane, 2,2-bis(4-cyanooxyphenyl) base)-1,1,1,3,3,3-hexafluoropropane, bis(4-cyanooxyphenyl)phenylmethane, 1,1-bis(4-cyanooxyphenyl)-1- Phenylethane, bis(4-cyanooxyphenyl)biphenylmethane, 1,1-bis(4-cyanooxyphenyl)cyclopentane, 1,1-bis(4-cyanooxyphenyl) ) cyclohexane, 2,2-bis(4-cyanooxy-3-isopropylphenyl)propane, 1,1-bis(3-cyclohexyl-4-cyanooxyphenyl)cyclohexane, Bis(4-cyanooxyphenyl)diphenylmethane, bis(4-cyanooxyphenyl)-2,2-dichloroethylene, 1,3-bis[2-(4-cyanooxyphenyl) )-2-propyl]benzene, 1,4-bis[2-(4-cyanooxyphenyl)-2-propyl]benzene, 1,1-bis(4-cyanooxyphenyl)-3 ,3,5-trimethylcyclohexane, 4-[bis(4-cyanooxyphenyl)methyl]biphenyl, 4,4-dicyanooxybenzophenone, 1,3-bis( 4-cyanoxyphenyl)-2-propen-1-one, bis(4-cyanoxyphenyl) ether, bis(4-cyanoxyphenyl) sulfide, bis(4-cyanoxyphenyl) base) phenyl, 4-cyanooxyphenyl 4-cyanobenzoate (4-cyanooxyphenyl-4-cyanooxybenzoate), bis-(4-cyanooxyphenyl) Carbonate, 1,3-bis(4-cyanooxyphenyl)adamantane, 1,3-bis(4-cyanooxyphenyl)-5,7-dimethyladamantane, 3,3-bis (4-cyanooxyphenyl)isobenzofuran-1(3H)-one (cyanate ester of phenolphthalein), 3,3-bis(4-cyanooxy-3-methylphenyl)isobenzofuran Furan-1(3H)-one (cyanate ester of o-cresolphthalein), 9,9-bis(4-cyanooxyphenyl)fluorene, 9,9-bis(4-cyanooxy-3-methyl Phenyl)fluorene, 9,9-bis(2-cyanooxy-5-biphenyl)fluorene, tris(4-cyanooxyphenyl)methane, 1,1,1-tris(4-cyanooxy) Phenyl)ethane, 1,1,3-tris(4-cyanophenyl)propane, α,α,α'-tris(4-cyanophenyl)-1-ethyl-4-iso Propylbenzene, 1,1,2,2-tetrakis(4-cyanophenyl)ethane, tetrakis(4-cyanophenyl)methane, 2,4,6-tris(N-methyl- 4-cyanooxyanilino)-1,3,5-triazine, 2,4-bis(N-methyl-4-cyanooxyanilino)-6-(N-methylanilino)-1 ,3,5-triazine, bis(N-4-cyanooxy-2-methylphenyl)-4,4'-oxydiphthalimide, bis(N-3-cyanooxy Base-4-methylphenyl)-4,4'-oxydiphthalimide, bis(N-4-cyanooxyphenyl)-4,4'-oxydiphthalimide Imide, bis(N-4-cyanooxy-2-methylphenyl)-4,4'-(hexafluoroisopropylidene)diphthalimide, tris(3,5- Dimethyl-4-cyanooxybenzyl)isocyanurate, 2-phenyl-3,3-bis(4-cyanooxyphenyl)benzyl carboxamide, 2-(4-methyl Phenyl)-3,3-bis(4-cyanooxyphenyl)benzyl carboxamide, 2-phenyl-3,3-bis(4-cyanooxy-3-methylphenyl)benzyl carboxamide Lactam, 1-methyl-3,3-bis(4-cyanooxyphenyl)indolin-2-one, 2-phenyl-3,3-bis(4-cyanooxyphenyl) Indolin-2-one, phenol novolac resin or cresol novolak resin (by conventional methods, formaldehyde compounds such as formalin or polyoxymethylene and phenol, alkyl-substituted phenol or halogen-substituted phenol in acidic solution), trisphenol novolak resin (reacting hydroxybenzaldehyde and phenol in the presence of an acidic catalyst), fluorene novolak resin (reacting fluorenone compound and 9,9-bis(hydroxyaryl) fluorene In the presence of an acidic catalyst, the reactant), phenol aralkyl resin, cresol aralkyl resin, naphthol aralkyl resin or biphenyl aralkyl resin (by a known method, will be Ar ₅ -( CH ₂ Z') ₂ Reaction of bishalogenated methyl _compounds with phenolic compounds _under acidic catalyst or without catalyst _; Reaction of a bis(hydroxymethyl) compound represented by Ar ₅ -(CH ₂ OH) ₂ with a phenolic compound in the presence of an acidic catalyst; or polycondensation of an aromatic aldehyde compound, an aralkyl compound, or a phenolic compound ), phenol-modified xylene formaldehyde resin (by the known method, the xylene formaldehyde resin and the phenolic compound are reacted in the presence of an acidic catalyst), modified naphthalene formaldehyde resin (by the known method, the naphthalene Formaldehyde resin and hydroxyl-substituted aromatic compound react in the presence of acidic catalyst), phenol-modified dicyclopentadiene resin, phenol resin with polynaphthylene ether structure (by known method , dehydration condensation of a polyvalent hydroxynaphthalene compound having two or more phenolic hydroxyl groups in one molecule in the presence of a basic catalyst), etc., which are cyanated by the same method as above, but There are no particular restrictions. These cyanate compounds may be used alone or in combination of two or more.

Among them, phenol novolak type cyanate compounds, naphthol arane type cyanate compounds, naphthyl ether type cyanate compounds, bisphenol A type cyanate compounds, bisphenol M type cyanate compounds are preferable. 1. A diallyl bisphenol type cyanate compound, particularly preferably a naphthol arane type cyanate compound. The cured product of the resin composition using these cyanate ester compounds has excellent characteristics such as low dielectric properties (low permittivity, low dielectric loss tangent).

The content of the cyanate compound in the resin composition can be appropriately set in accordance with desired properties, and is not particularly limited. Specifically, the content of the cyanate compound, when contained, is preferably at least 0.1 part by mass, more preferably at least 0.5 part by mass, more preferably at least 0.5 part by mass, relative to 100 parts by mass of resin solids in the resin composition It may be 1 mass part or more, 3 mass parts or more, 5 mass parts or more. In addition, the upper limit of the content is preferably 90 parts by mass or less, more preferably 80 parts by mass or less, more preferably less than 70 parts by mass, still more preferably 60 parts by mass or less, and may be 50 parts by mass Less than or equal to 40 parts by mass. By falling within such a range, more excellent low permittivity properties and low dielectric loss tangent properties can be imparted. A cyanate compound may be used only by 1 type, and may use 2 or more types. When using two or more, the total amount is preferably within the above range.

(epoxy resin) The resin composition may contain an epoxy resin as a thermosetting compound. Epoxy resins, as long as they have one or more (preferably 2 to 12, more preferably 2 to 6, more preferably 2 to 4, still more preferably 2 or 3, still more preferably 2) The epoxy compound or resin is not particularly limited, for example, bisphenol A type epoxy resin, bisphenol E type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin Resin, phenol novolac epoxy resin, bisphenol A novolac epoxy resin, glycidyl ester epoxy resin, aralkyl novolak epoxy resin, biphenyl arane epoxy resin, naphthyl ether Type epoxy resin, cresol novolak type epoxy resin, multifunctional phenol type epoxy resin, naphthalene type epoxy resin, anthracene type epoxy resin, naphthalene skeleton modified novolak type epoxy resin, phenol arane type ring Oxygen resin, naphthol arane type epoxy resin, dicyclopentadiene type epoxy resin, biphenyl type epoxy resin, alicyclic epoxy resin, polyol type epoxy resin, phosphorus epoxy resin, shrinkage Glycerylamine, glycidyl ester, compounds obtained by epoxidizing double bonds of butadiene, compounds obtained by reacting hydroxyl-containing silicone resins with epichlorohydrin, etc. These epoxy resins may be used alone or in combination of two or more. Among them, from the viewpoint of further improving flame retardancy and heat resistance, biphenyl arane type epoxy resins, naphthyl ether type epoxy resins, polyfunctional phenol type epoxy resins, naphthalene type epoxy resin.

(phenolic resin) The resin composition may contain a phenol resin as a thermosetting compound. Phenolic resins, as long as they have one or more (preferably 2-12, more preferably 2-6, more preferably 2-4, still more preferably 2 or 3, still more preferably 2) in one molecule ) of the phenolic hydroxyl group or resin is not particularly limited, for example, bisphenol A type phenol resin, bisphenol E type phenol resin, bisphenol F type phenol resin, bisphenol S type phenol resin, phenol novolac Resin, bisphenol A novolak type phenol resin, glycidyl ester type phenol resin, aralkyl novolac phenol resin, biphenyl aralkyl type phenol resin, cresol novolak type phenol resin, multifunctional phenol resin, naphthol resin, Naphthol novolak resins, multifunctional naphthol resins, anthracene-type phenol resins, naphthalene-skeleton-modified novolac-type phenol resins, phenol-aralkyl-type phenol resins, naphthol-aralkyl-type phenol resins, dicyclopentadiene-type phenol resins , biphenyl phenol resins, alicyclic phenol resins, polyol phenol resins, phosphorus-containing phenol resins, etc. These phenolic resins may be used alone or in combination of two or more. Among these, at least one selected from the group consisting of biphenyl aralkyl phenol resins, naphthol aralkyl phenol resins, and phosphorus-containing phenol resins is preferable from the viewpoint of further improving flame resistance.

(thermoplastic elastomer) The resin composition may contain a thermoplastic elastomer. Thermoplastic elastomers containing styrene monomer units. By containing styrene monomer units, the solubility of the thermoplastic elastomer resin composition is improved. Styrene monomers, examples: styrene, α-methylstyrene, p-methylstyrene, divinylbenzene (vinylstyrene), N,N-dimethyl-p-aminoethylstyrene , N,N-diethyl-p-aminoethylstyrene, etc. Among them, styrene, α-methylstyrene, p-methylstyrene are preferable from the viewpoint of availability and productivity. styrene. Among these, styrene is particularly preferred. The content of the styrene monomer unit (styrene ratio) of the above-mentioned thermoplastic elastomer is preferably in the range of 10 to 50% by mass of all monomer units, more preferably in the range of 13 to 45% by mass, still more preferably The range of 15 to 40% by mass. When the content of the styrene monomer unit is 50% by mass or less, the adhesiveness and adhesiveness to the substrate and the like will become more favorable. Moreover, when it is 10 mass % or more, since it can suppress an increase in adhesion, a residual paste or a stop mark (stop mark) will hardly generate|occur|produce, and since it exists in the tendency for the easy peelability of an adhesive surface to become favorable, it is preferable. Thermoplastic elastomers may contain only one type of styrene monomer unit, or may contain two or more types. When two or more of them are included, the total amount is preferably within the above-mentioned range. For the measurement method of the content of the styrene monomer unit in the thermoplastic elastomer of this embodiment, reference may be made to the records in International Publication No. 2017/126469, and the content is included in this specification. The same applies to conjugated diene monomer units and the like described later.

The above-mentioned thermoplastic elastomer contains conjugated diene monomer units. By containing the conjugated diene monomer unit, the solubility of the thermoplastic elastomer resin composition is improved. The conjugated diene monomer is not particularly limited as long as it is a diene having a pair of conjugated double bonds. Conjugated diene monomers, for example, 1,3-butadiene, 2-methyl-1,3-butadiene (isoprene), 2,3-dimethyl-1,3- butadiene, 1,3-pentadiene, 2-methyl-1,3-pentadiene, 1,3-hexadiene, and chlorophyllene, preferably 1,3-butadiene, and Isoprene, more preferably 1,3-butadiene. The thermoplastic elastomer may contain only one kind of conjugated diene monomer unit, or may contain two or more kinds.

In the above thermoplastic elastomer, the mass ratio of styrene monomer unit to conjugated diene monomer unit is preferably in the range of styrene monomer unit/conjugated diene monomer unit = 5/95 to 80/20 , more preferably in the range of 7/93 to 77/23, more preferably in the range of 10/90 to 70/30. When the mass ratio of the aforementioned styrene monomer unit to the conjugated diene monomer unit is in the range of 5/95 to 80/20, it is possible to suppress the increase in adhesion and maintain a high degree of adhesive force, and the ease of peeling of the adhesive surfaces becomes better. good.

The above-mentioned thermoplastic elastomer may contain other monomer units in addition to the styrene monomer unit and the conjugated diene monomer unit, or may not contain other monomer units. Other monomer units include aromatic vinyl compound units other than styrene monomer units, and the like. In the above-mentioned thermoplastic elastomer, the total of the styrene monomer unit and the conjugated diene monomer unit is preferably at least 90% by mass of all the monomer units, more preferably at least 95% by mass, still more preferably at least 97% by mass. Above, more preferably 99% by mass or more. As mentioned above, in a thermoplastic elastomer, a styrene monomer unit and a conjugated diene monomer unit may contain only one kind individually, and may contain two or more types individually. When two or more of them are included, the total amount is preferably within the above-mentioned range.

The thermoplastic elastomer used in this embodiment can be a block polymer or a random polymer. In addition, the conjugated diene monomer unit may be a hydrogenated elastomer that is hydrogenated, may be a non-hydrogenated elastomer that is not hydrogenated, or may be a partially hydrogenated elastomer that has been partially hydrogenated.

Examples of commercially available thermoplastic elastomers used in this embodiment include SEPTON (registered trademark) 2104 manufactured by Kuraray Co., Ltd., DYNARON (registered trademark) 9901P and TR2250 manufactured by JSR Co., Ltd., and the like.

When the resin composition contains a thermoplastic elastomer, the content thereof is preferably at least 1 part by mass, more preferably at least 3 parts by mass, and more preferably at least 5 parts by mass, with respect to 100 parts by mass of the resin solid content. More preferably, it is 8 mass parts or more, and it is still more preferable that it is 10 mass parts or more. There exists a tendency for a low dielectric characteristic to be further improved by being more than the said lower limit. In addition, the upper limit of the thermoplastic elastomer content is preferably not more than 45 parts by mass, more preferably not more than 40 parts by mass, and more preferably not more than 35 parts by mass, with respect to 100 parts by mass of the resin solid content. More preferably, it is 32 mass parts or less, Still more preferably, it is 28 mass parts or less. There exists a tendency for heat resistance to be improved more by being below the said upper limit. The resin composition may contain only one type of thermoplastic elastomer, or may contain two or more types. When two or more of them are included, the total amount is preferably within the above-mentioned range.

(Filler) The resin composition may also contain a filler in order to improve low permittivity and low dielectric loss tangent. As the filler, known materials can be used as appropriate, and the type is not particularly limited, and those generally used in the field can be used as appropriate. Specifically, silicas such as natural silica, fused silica, synthetic silica, amorphous silica, aerosil, and hollow silica; white carbon , titanium dioxide, zinc oxide, magnesium oxide, zirconia, boron nitride, agglomerated boron nitride, silicon nitride, aluminum nitride, barium sulfate, aluminum hydroxide, aluminum hydroxide heat-treated products (heat-treated aluminum hydroxide, Metal hydrates such as boehmite and magnesium hydroxide; molybdenum compounds such as molybdenum oxide or zinc molybdate; zinc borate, zinc stannate, alumina, clay, kaolin, talc, calcined clay , calcined kaolin, calcined talc, mica, E-glass, A-glass, NE-glass, C-glass, L-glass, D-glass, S-glass, M-glass G20, glass short fiber (including E glass, In addition to inorganic fillers such as T glass, D glass, S glass, Q glass, etc.), insulating glass, spherical glass, etc., styrene type, butadiene type, acrylic type Such as rubber powder; core-shell rubber powder, silicone resin powder, silicone rubber powder, silicon composite powder and other organic fillers. These fillers may be used alone or in combination of two or more. Among these, one or more kinds selected from the group consisting of silica, aluminum hydroxide, boehmite, magnesium oxide, and magnesium hydroxide are suitable. By using these fillers, properties such as thermal expansion characteristics, dimensional stability, and flame retardancy of the resin composition are improved.

The content of the filler in the resin composition can be appropriately set according to the desired characteristics, and is not particularly limited. When it is contained, it is preferably 50 parts by mass relative to 100 parts by mass of the resin solid content in the resin composition. servings or more. The upper limit is preferably at most 1600 parts by mass, more preferably at most 500 parts by mass, and particularly preferably at most 300 parts by mass. Alternatively, the filler may be 75 to 250 parts by mass, or may be 100 to 200 parts by mass. By making content of a filler into this range, the moldability of a resin composition becomes favorable. The resin composition may contain only one kind of filler, or may contain two or more kinds. When two or more of them are included, the total amount is preferably within the above-mentioned range.

Moreover, when using a filler, it is preferable to use together at least 1 sort(s) selected from the group of a silane coupling agent and a wetting and dispersing agent. As the silane coupling agent, those generally used for surface treatment of inorganic substances can be suitably used, and the type is not particularly limited. Specifically, aminosilane series such as γ-aminopropyltriethoxysilane and N-β-(aminoethyl)-γ-aminopropyltrimethoxysilane; γ-cyclo Oxypropoxypropyltrimethoxysilane, β-(3,4-epoxycyclohexyl)ethyltrimethoxysilane and other epoxysilane series; γ-methacryloxypropyltrimethoxysilane, Vinyl-tris(β-methoxyethoxy)silane and other vinyl silane series; N-β-(N-vinylbenzylaminoethyl)-γ-aminopropyltrimethoxysilane salt Cationic silanes such as acid salts, phenyl silanes, etc. Silane coupling agents can be used alone or in combination of two or more. In addition, as a wetting and dispersing agent, those generally used for paints can be suitably used, and the type is not particularly limited. It is preferable to use a wetting and dispersing agent with a copolymer base. Specific examples include: Disperbyk-110, 111, 161, 180, 2009, 2152, BYK-W996, BYK-W9010, BYK manufactured by BYK Chemical Co., Ltd. -W903, BYK-W940, etc. Wetting and dispersing agents can be used alone or in combination of two or more.

The content of the silane coupling agent is not particularly limited, but may be about 1 to 5 parts by mass relative to 100 parts by mass of the resin solid content in the resin composition. The content of the dispersant (particularly a wetting and dispersing agent) is not particularly limited, but may be, for example, about 0.5 to 5 parts by mass relative to 100 parts by mass of the resin solid content in the resin composition.

(styrene oligomer) The resin composition may contain styrene oligomers. The styrene oligomer of this embodiment is formed by polymerizing at least one selected from the group consisting of styrene, styrene derivatives, and vinyl toluene, and has a number average molecular weight of 178-1600, an average aromatic A non-branched compound with a ring number of 2 to 14, a total amount of 2 to 14 aromatic rings of 50% by mass or more, and a boiling point of 300°C or higher. By containing styrene oligomers, low permittivity and low dielectric loss tangent properties can be improved. Also, the "styrene oligomer" used in this embodiment is different from the above-mentioned "thermoplastic elastomer".

Styrene oligomers, for example, styrene polymers, vinyltoluene polymers, α-methylstyrene polymers, vinyltoluene-α-methylstyrene polymers, styrene-α-styrene polymer etc. As the styrene polymer, commercially available products can be used, for example, Piccolastic A5 (manufactured by Eastman Chemical Co., Ltd.), Piccolastic A-75 (manufactured by Eastman Chemical Co., Ltd.), Piccotex 75 (manufactured by Eastman Chemical Co., Ltd.), FTR-8100 (manufactured by Mitsui Chemicals Co., Ltd. Corporation), FTR-8120 (Mitsui Chemicals Co., Ltd.). In addition, examples of vinyltoluene-α-methylstyrene polymers include Piccotex LC (manufactured by Eastman Chemical Co., Ltd.). In addition, examples of the α-methylstyrene polymer include Kristalex 3070 (manufactured by Eastman Chemical Co., Ltd.), Kristalex 3085 (manufactured by Eastman Chemical Co., Ltd.), Kristalex (3100), Kristalex 5140 (manufactured by Eastman Chemical Co., Ltd.), FMR-0100 (manufactured by Mitsui Chemicals Co., Ltd. ), FMR-0150 (manufactured by Mitsui Chemicals Co., Ltd.). In addition, examples of the styrene-α-styrene polymer include FTR-2120 (manufactured by Mitsui Chemicals Co., Ltd.). These styrene oligomers may be used alone or in combination of two or more.

The content of styrene oligomers in the resin composition, when contained, is relative to 100 parts by mass of the resin solid content of the resin composition, from the perspective of low permittivity, low dielectric loss tangent and chemical resistance. From a viewpoint, it is preferably 1 to 30 parts by mass, particularly preferably 5 to 20 parts by mass, and may be 15 parts by mass or less. The resin composition may contain only one type of styrene oligomer, or may contain two or more types. When two or more of them are included, the total amount is preferably within the above-mentioned range.

(flame retardant) The resin composition may contain a flame retardant in order to improve flame resistance. Flame retardant, known ones can be used, for example, can enumerate: brominated epoxy resin, brominated polycarbonate, brominated polystyrene, brominated styrene, brominated phthalimide, tetra Bromobisphenol A, pentabromobenzyl (meth)acrylate, pentabromotoluene, tribromophenol, hexabromobenzene, decabromodiphenyl ether, bis-1,2-pentabromophenylethane, chlorinated polyphenylene Halogen-based flame retardants such as ethylene and chlorinated paraffin; red phosphorus, tricresyl phosphate, triphenyl phosphate, cresyl diphenyl phosphate, tricresyl phosphate, trialkyl phosphate, dialkyl phosphate, Tris(chloroethyl) phosphate, phosphazene, 1,3-phenylene bis(2,6-xylyl phosphate), 10-(2,5-dihydroxyphenyl)-10H-9-oxy Phosphorus-based flame retardants such as hetero-10-phenanthrene-10-phosphate phosphate; inorganic flame retardants such as aluminum hydroxide, magnesium hydroxide, some boehmite, boehmite, zinc borate, antimony trioxide, etc. ; Silicon-based flame retardants for silicone rubber, silicone resin, etc. These flame retardants may be used alone or in combination of two or more. Among them, phosphorus-based flame retardants are preferred, and especially 1,3-phenylene bis(2,6-xylyl phosphate) is preferred because it hardly impairs low dielectric properties. The phosphorus content in the resin composition is preferably 0.1% by mass to 5% by mass.

The content of the flame retardant, when contained, is preferably at least 1 part by mass, more preferably at least 5 parts by mass, based on 100 parts by mass of the resin solid content in the resin composition. In addition, the upper limit of the content is preferably 30 parts by mass or less, more preferably 20 parts by mass or less, and may be 15 parts by mass or less. As the flame retardant, only one kind may be used, or two or more kinds may be used. When two or more are used, the total amount is preferably within the above range.

(other ingredients) Furthermore, the resin composition may contain polyphenylene ether compounds, oxetane resins, benzoxazine compounds, unsaturated polyphenylene ethers, etc. Thermoplastic elastomers containing styrene monomer units (hereinafter referred to as "other thermoplastic elastomers"), hardening accelerators, organic solvents, etc. By using these in combination, desired characteristics such as low dielectric properties can be improved. In the resin composition, the total amount of polyphenylene ether compounds other than the above-mentioned polyphenylene ether compound and the above-mentioned other thermoplastic elastomers is preferably 3% by mass or less, more preferably 1% by mass or less, of the resin solid content. With such a configuration, the effects of the present invention can be exhibited more effectively.

(oxetane resin) Oxetane resins are not particularly limited, for example, oxetane, alkyl oxetane (for example, 2-methyl oxetane, 2,2-dimethyl oxetane, 3-methyloxetane, 3,3-dimethyloxetane, etc.), 3-methyl-3-methoxymethyloxetane, 3 ,3-bis(trifluoromethyl)perfluorooxetane, 2-chloromethyloxetane, 3,3-bis(chloromethyl)oxetane, biphenyl-type oxetane Cyclobutane, OXT-101 (product of Toagosei Co., Ltd.), OXT-121 (product of Toagosei Co., Ltd.), etc. These oxetane resins may be used alone or in combination of two or more.

(Benzoxazine compound) The benzoxazine compound is not particularly limited as long as it is a compound having two or more dihydrobenzoxazine rings in one molecule, for example, bisphenol A type benzoxazine BA-BXZ (Konishi Chemical Co., Ltd. Co., Ltd.), bisphenol F-type benzoxazine BF-BXZ (product of Konishi Chemical Co., Ltd.), bisphenol S-type benzoxazine BS-BXZ (product of Konishi Chemical Co., Ltd.), etc. These benzoxazine compounds may be used alone or in combination of two or more.

(other thermoplastic elastomers) Other thermoplastic elastomers refer to elastomers other than the aforementioned thermoplastic elastomers. Other thermoplastic elastomers include, for example, those selected from polyisoprene, polybutadiene, butyl rubber, ethylene propylene rubber, fluororubber, silicone rubber, their hydrogenated compounds, and their alkyl compounds. At least one of the group. Among them, the one selected from the group consisting of polyisoprene, polybutadiene, butyl rubber, and ethylene propylene rubber is more preferable from the viewpoint of better compatibility with polyphenylene ether compounds. at least one.

(hardening accelerator) The resin composition may also contain a curing accelerator for appropriately adjusting the curing rate. Hardening accelerators include those commonly used as hardening accelerators such as maleimide compounds and epoxy resins, including organic metal salts (for example, zinc octoate, zinc naphthenate, cobalt naphthenate, cycloalkanoate, etc.) Copper alkanoate, iron acetylacetonate, nickel octoate, manganese octoate, etc.), phenolic compounds (such as phenol, xylenol, cresol, resorcinol, catechol, octylphenol, nonylphenol, etc.) , alcohols (for example, 1-butanol, 2-ethylhexanol, etc.), imidazoles (for example, 2-methylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 1- Cyanoethyl-2-phenylimidazole, 1-cyanoethyl-2-ethyl-4-methylimidazole, 2-phenyl-4,5-dihydroxymethylimidazole, 2-phenyl-4-methanol -5-hydroxymethylimidazole, etc.) and derivatives of these imidazole carboxylic acids or adducts of their anhydrides, amines (such as dicyanoamide, benzyldimethylamine, 4-methyl-N,N-dimethylbenzylamine, etc.), phosphorus compounds (such as phosphine-based compounds, phosphine oxide-based compounds, phosphonium salt-based compounds, diphosphine-based compounds, etc.), epoxy-imidazole addition compounds, peroxides (e.g., benzoyl peroxide, p-chlorobenzoyl peroxide, di-tertiary butyl peroxide, diisopropyl peroxycarbonate, di-2-ethyl peroxycarbonate hexyl ester, etc.), azo compounds (for example, azobisisobutyronitrile, etc.). The hardening accelerators may be used alone or in combination of two or more. The content of the hardening accelerator is usually about 0.005 to 10 parts by mass relative to 100 parts by mass of the resin solid content in the resin composition.

The resin composition may contain various high molecular compounds such as thermosetting resins, thermoplastic resins, and oligomers thereof, and various additives other than the above-mentioned components. Additives include: ultraviolet absorbers, antioxidants, photopolymerization initiators, fluorescent whitening agents, photosensitizers, dyes, pigments, thickeners, flow regulators, lubricants, defoamers, dispersants, homogenizers, Dye, gloss agent, polymerization inhibitor, etc. These additives may be used alone or in combination of two or more.

＜Organic solvent＞ The prepreg may also contain organic solvents. In this case, the resin composition of this embodiment is a form (solution or varnish) in which at least a part, preferably all, of the above-mentioned various resin components are dissolved or compatible in an organic solvent. The organic solvent is not particularly limited as long as it is a polar organic solvent or non-polar organic solvent that can dissolve or dissolve at least a part of the above-mentioned various resin components, preferably all; polar organic solvents, for example, can enumerate: ketones (for example, acetone, methyl ethyl ketone, methyl isobutyl ketone, etc.), celluloids (e.g., propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, etc.), esters (e.g., ethyl lactate, methyl acetate, ethyl acetate , butyl acetate, isoamyl acetate, ethyl lactate, methyl methoxypropionate, methyl hydroxyisobutyrate, etc.), amides (for example, dimethoxyacetamide, dimethylformamide amines, etc.); non-polar organic solvents, aromatic hydrocarbons (for example, toluene, xylene, etc.) can be mentioned. These organic solvents may be used alone or in combination of two or more.

[use] The prepreg of this embodiment can be suitably used as an insulating layer of a printed wiring board.

[Laminated board] A laminated board is one that heats and presses a laminate including one or more prepregs of this embodiment to harden the prepreg, and is formed by including the prepreg of this embodiment The layer includes the cured product of the prepreg of this embodiment. The forming method and forming conditions of the laminate are not particularly limited, and general methods and conditions can be used. For example, a multistage press machine, a multistage vacuum press machine, a continuous molding machine, an autoclave molding machine, etc. can be used for molding. In molding (lamination molding), the temperature is generally 100°C to 300°C, the pressure is 2kgf/cm ² to 100kgf/cm ² , and the heating time is in the range of 0.05 to 5 hours. Furthermore, post-hardening may also be performed at the temperature of 150 degreeC - 300 degreeC as needed. Especially in the case of using a multi-stage pressing machine, from the viewpoint of sufficiently accelerating the hardening of the prepreg, the temperature is preferably 200°C to 250°C, the pressure is 10kgf/cm ² to 40kgf/cm ² , and the heating time is 80 minutes to 130 minutes, more preferably a temperature of 215°C to 235°C, a pressure of 25kgf/cm ² to 35kgf/cm ² , and a heating time of 90 minutes to 120 minutes.

[Printed Wiring Board] The printed wiring board has an insulating layer and a conductive layer, and the insulating layer includes a layer formed of the prepreg of this embodiment, that is, a cured product of the prepreg of this embodiment. Such a printed wiring board can be manufactured according to a conventional method, and the manufacturing method is not particularly limited. Hereinafter, an example of the manufacturing method of a printed wiring board is shown. First, a metal foil-clad laminate such as a copper-clad laminate in which one or more prepregs are stacked and metal foil is arranged on one or both sides is prepared. Next, an etching process is applied to the surface of the metal foil-clad laminate to form an inner layer circuit to produce an inner layer substrate. On the surface of the inner layer circuit of the inner layer substrate, if necessary, perform surface treatment in order to improve the bonding strength, and then overlap the above-mentioned prepreg on the surface of the inner layer circuit by the required number, and further laminate the metal for the outer layer circuit on the outside. foil, and heat and press to integrally form. In this manner, a multilayer laminate in which an insulating layer made of a cured prepreg is formed between the inner layer circuit and the metal foil for the outer layer circuit is manufactured. Next, after processing the hole for a through hole or a via hole on the multi-layer laminate, a plated layer is formed on the wall of the hole to conduct the inner layer circuit and the metal foil for the outer layer circuit. Metal-coated film, and further etched on the metal foil for the outer circuit to form the outer circuit, so as to manufacture the printed wiring board.

Thus, according to the present embodiment, since the ratio of the resin composition, the relative permittivity, and the dielectric loss tangent are adjusted, SKEW and transmission loss can be reduced, and the signal speed can be increased. Accordingly, it is possible to cope with high frequencies. [Example]

(Synthesis Example 1) Synthesis of Naphthol Aralkyl Cyanate Compound (SNCN) 300 g (OH group conversion: 1.28 mol) of 1-Naphthol Aralkyl Resin (manufactured by Nippon Steel & Sumikin Chemical Co., Ltd.) and triethylamine 194.6 g (1.92 mol) (1.5 mol relative to 1 mol of hydroxyl groups) was dissolved in 1800 g of dichloromethane, and this was used as solution 1. Stir 125.9g (2.05mol) of cyanogen chloride (1.6mol to 1mol of hydroxyl), 293.8g of dichloromethane, 194.5g (1.92mol) of 36% hydrochloric acid (1.5mol to 1mol of hydroxyl), and 1205.9g of water Solution 1 was injected over 30 minutes while maintaining the liquid temperature at -2°C to -0.5°C. After the injection of solution 1 was completed, after stirring at the same temperature for 30 minutes, a solution (solution 2) in which 65 g (solution 2) of triethylamine (0.5 mol per 1 mol of hydroxyl group) was dissolved in 65 g of methylene chloride was injected over 10 minutes. After solution 2 was injected, it was stirred at the same temperature for 30 minutes to complete the reaction. Then the reaction solution was left standing to separate the organic phase and the aqueous phase. The obtained organic phase was washed 5 times with 1300 g of water. The electrical conductivity of the wastewater washed with water for the fifth time was 5 μS/cm, and it was confirmed that the removable ionic compounds were sufficiently removed by washing with water. The organic phase washed with water was concentrated under reduced pressure, and finally concentrated to dryness at 90° C. for 1 hour to obtain 331 g of the target naphthol arane-type cyanate compound (SNCN) (orange sticky substance). The weight average molecular weight Mw of the obtained SNCN was 600. In addition, the IR spectrum of SNCN showed absorption at 2250 cm ^-1 (cyanate group), and did not show absorption at hydroxyl group.

(Example 1) As the resin solid component of the resin composition, prepare: in general formula (11), R ₅₁ and R ₅₂ are hydrogen atoms, and n ₄ is a maleimide compound (BMI-2300 , Daiwa Chemical Industry Co., Ltd.) 15 parts by mass; 35 parts by mass of the cyanate compound (SNCN) obtained in Synthesis Example 1; in general formula (5), polymerization X is general formula (6), -(YO) n ₂ - Terminally unsaturated group-modified polyphenylene ether composed of structural units of general formula (9) (OPE-2St1200, manufactured by Mitsubishi Gas Chemical Co., Ltd., number average molecular weight: 1187, vinyl equivalent: 590g/eq.) 10 parts by mass; as the second component of terminal unsaturated group-modified polyphenylene ether, in general formula (5), polymerization X is general formula (6), -(YO)n ₂ - is the structure of general formula (9) 10 parts by mass of terminal unsaturated group-modified polyphenylene ether (OPE-2St2200, manufactured by Mitsubishi Gas Chemical Co., Ltd., number average molecular weight: 2200, vinyl equivalent: 1100 g/eq.); styrene-isoprene - 10 parts by mass of styrene elastomer (SEPTON 2104, manufactured by Kuraray Co., Ltd., styrene ratio: 65%); 20 parts by mass of α-methylstyrene polymer (Kristalex 3085, manufactured by Eastman Chemical Co., Ltd.). 100 parts by mass of this resin solid content and 150 parts by mass of spherical silica (SC2050-MB, manufactured by Admatechs Co., Ltd., average particle diameter: 0.5 μm) as a filler were mixed and diluted with methyl ethyl ketone as an organic solvent to obtain a varnish. This varnish was dip-coated on low-dielectric glass cloth with a thickness of 32 μm as a glass fiber substrate, and heated and dried at 165° C. for 5 minutes using a dryer (pressure-resistant explosion-proof steam dryer, manufactured by Takasugi Seisakusho Co., Ltd.) to obtain prepreg. The ratio of the resin composition (resin solid content + filler in Example 1) to the total amount of the prepreg was 87.6% by volume.

(Example 2) In addition to using low-dielectric glass cloth with a thickness of 19 μm as the glass fiber substrate, and the ratio of the resin composition (resin solid content + filler in Example 2) to the total amount of the prepreg is 92.1% by volume, other A prepreg was produced in the same manner as in Example 1.

(Example 3) In addition to using low-dielectric glass cloth with a thickness of 14 μm as the glass fiber substrate, and the ratio of the resin composition (resin solid content + filler in Example 3) to the total amount of the prepreg is 95.1% by volume, other A prepreg was produced in the same manner as in Example 1.

(Example 4) As the resin solid component of the resin composition, prepare: 40 parts by mass of a maleimide compound (MIR-5000, manufactured by Nippon Kayaku Co., Ltd.) shown in the general formula (15); the general formula ( In 5), the polymerization X is a _terminal unsaturated group modified polyphenylene ether (OPE-2St2200, Mitsubishi Gas Chemical Co., Ltd. Made by the company, number average molecular weight 2200, vinyl equivalent: 1100 g/eq.) 35 parts by mass; styrene-butadiene block copolymer (TR2250, manufactured by JSR Co., Ltd., styrene ratio: 52%) 25 parts by mass. The resin solid components were mixed and diluted with methyl ethyl ketone as an organic solvent to obtain a varnish. This varnish was dip-coated on low-dielectric glass cloth with a thickness of 14 μm as a glass fiber substrate, and heated and dried at 165° C. for 3 minutes using a dryer (pressure-resistant explosion-proof steam dryer, manufactured by Takasugi Seisakusho Co., Ltd.) to obtain prepreg. The ratio of the resin composition (resin solid content in Example 4) to the total amount of the prepreg was 95.1% by volume.

(Example 5) In addition to using low-dielectric glass cloth with a thickness of 9 μm as the glass fiber substrate, and the ratio of the resin composition (resin solid content + filler in Example 5) to the total amount of the prepreg is 96.7% by volume, other A prepreg was produced in the same manner as in Example 4.

(Example 6) As the resin solid component of the resin composition, prepare: in the general formula (11), R ₅₁ and R ₅₂ are hydrogen atoms, and n ₄ is a maleimide compound (BMI-2300 , Daiwa Chemical Industry Co., Ltd.) 10 parts by mass; 30 parts by mass of the cyanate compound (SNCN) obtained in Synthesis Example 1; in general formula (5), polymerization X is general formula (6), -(YO) n ₂ - 60 parts by mass of polyphenylene ether compound (OPE-2St1200, manufactured by Mitsubishi Gas Chemical Co., Ltd., number average molecular weight: 1187, vinyl equivalent: 590 g/eq.) composed of structural units of general formula (9). 100 parts by mass of the resin solid content, 100 parts by mass of spherical silica (SC2050-MB, manufactured by Admatechs Co., Ltd., average particle size 0.5 μm) as a filler, and 0.1 part by mass of zinc octylate as a hardening accelerator were mixed, and Dilute it with methyl ethyl ketone as an organic solvent to obtain a varnish. This varnish was dip-coated on low-dielectric glass cloth with a thickness of 32 μm as a glass fiber substrate, and heated and dried at 165° C. for 5 minutes using a dryer (pressure-resistant explosion-proof steam dryer, manufactured by Takasugi Seisakusho Co., Ltd.) to obtain prepreg. The ratio of the resin composition (resin solid content + filler + hardening accelerator in Example 6) to the total amount of the prepreg was 87.6% by volume.

(comparative example 1) In addition to using low-dielectric glass cloth with a thickness of 80 μm as the glass fiber substrate, and the ratio of the resin composition (resin solid content + filler in Comparative Example 1) to the total amount of the prepreg is 69.3% by volume, other A prepreg was produced in the same manner as in Example 1.

(comparative example 2) In addition to using low-dielectric glass cloth with a thickness of 49 μm as the glass fiber substrate, and the ratio of the resin composition (resin solid content + filler in Comparative Example 2) to the total amount of the prepreg is 78.8% by volume, other A prepreg was produced in the same manner as in Example 1.

(comparative example 3) In addition to using low-dielectric glass cloth with a thickness of 43 μm as the glass fiber substrate, and the ratio of the resin composition (resin solid content + filler in Comparative Example 3) to the total amount of the prepreg is 80.9% by volume, other A prepreg was produced in the same manner as in Example 1.

(comparative example 4) The same varnish as in Example 1 was coated on one side of a 12 μm thick copper foil (3EC-M3-VLP, manufactured by Mitsui Metal Mining Co., Ltd.) with a bar coater to obtain a copper-attached resin sheet. Using a dryer (pressure-resistant explosion-proof steam dryer, manufactured by Takasugi Seisakusho Co., Ltd.), heat and dry the obtained copper-attached resin sheet at 130°C for 5 minutes to obtain a semi-hardened copper-attached resin sheet with a resin thickness of 25 μm . The ratio of the resin composition (resin solid content+filler in Comparative Example 4) to the total amount of the resin sheet was 100% by volume.

(comparative example 5) The same varnish as in Example 4 was coated on one side of a 12 μm thick copper foil (3EC-M3-VLP, manufactured by Mitsui Metal Mining Co., Ltd.) with a bar coater to obtain a copper-attached resin sheet. Using a dryer (pressure-resistant explosion-proof steam dryer, manufactured by Takasugi Seisakusho Co., Ltd.), heat and dry the obtained copper-attached resin sheet at 130°C for 5 minutes to obtain a semi-hardened copper-attached resin sheet with a resin thickness of 25 μm . The ratio of the resin composition (resin solid content in Comparative Example 5) to the total amount of the resin sheet was 100% by volume.

(comparative example 6) As the resin solid content of the resin composition, prepare: 65 parts by mass of the cyanate compound (SNCN) obtained in Synthesis Example 1; : 320 g/eq., manufactured by Nippon Kayaku Co., Ltd.) 30 parts by mass; naphthalene skeleton type epoxy resin (HP-4032D, epoxy group equivalent: 140 g/eq., manufactured by DIC Corporation) 5 parts by mass. 100 parts by mass of the resin solid content, 100 parts by mass of spherical silica (SC2050-MB, manufactured by Admatechs Co., Ltd., average particle size 0.5 μm) as a filler, and 0.1 part by mass of zinc octylate as a hardening accelerator were mixed, and Dilute it with methyl ethyl ketone as an organic solvent to obtain a varnish. This varnish was dip-coated on E-glass cloth with a thickness of 32 μm as a glass fiber substrate, and heated and dried at 165° C. for 4 minutes using a dryer (pressure-resistant explosion-proof steam dryer, manufactured by Takasugi Seisakusho Co., Ltd.) to obtain a prepreg. body. The ratio of the resin composition (resin solid content + filler + hardening accelerator in Comparative Example 6) to the total amount of the prepreg was 87.6% by volume.

(Preparation of samples for evaluation) For the prepregs obtained in Examples 1-6 and Comparative Examples 1-3, 6, one or four sheets were stacked according to each Example and each Comparative Example, and copper foil was arranged on both sides (3EC-M3-VLP, manufactured by Mitsui Metal Mining Co., Ltd., thickness 12 μm), vacuum pressing (thermal hardening) was performed at a pressure of 30 kgf/cm ² and a temperature of 210°C for 150 minutes to obtain a layer formed of a prepreg. Copper clad laminates with a thickness of 0.1mm and 0.4mm. In addition, for the semi-cured copper-attached resin sheets obtained in Comparative Examples 4 and 5, two semi-cured copper-attached resin sheets were heated and laminated in a manner that the resin surfaces were in contact, and then the copper foil was peeled off, and the operation was further repeated for 1 Heat and laminate the upper and lower semi-hardened copper-attached resin sheets in a manner of contacting the resin surface one time or seven times, and peel off the copper foil to obtain a semi-hardened resin layer with a thickness of 0.1mm and 0.4mm on the two-layered copper foil The resin sheet. The semi-cured resin sheet with a resin layer thickness of 0.1mm and 0.4mm was vacuum-pressed at a pressure of 30 kgf/cm ² and a temperature of 210°C for 150 minutes to obtain a copper-clad foil with a resin layer thickness of 0.1mm and 0.4mm Laminate.

(Evaluation of Relative Permittivity Dk and Dielectric Loss Tangent Df) Using samples of copper clad laminates with a thickness of 0.4mm obtained by etching to remove the copper foil of each example and each comparative example, by the perturbation method cavity resonator (product of Agilent Technologies, Agilent8722ES) , Determination of relative permittivity and dielectric loss tangent at 10GHz. The obtained results are shown in Table 1, Table 2, and Fig. 1 .

(SKEW's evaluation) Only one side of the 0.1mm-thick copper-clad laminate obtained in each example and each comparative example was etched to form 15 microstrip lines with a circuit length of 10cm. Measure the transmission speed of 15 conductor wiring (resistance 50Ω) from 10GHz to 20GHz, and obtain SKEW (propagation delay time difference) from the difference between the maximum value and the minimum value. The obtained results are shown in Table 1, Table 2, and Fig. 2 .

(Evaluation of Transmission Loss) Only one side of the 0.1mm-thick copper-clad laminate obtained in each example and each comparative example was etched, and a wiring board with a microstrip line with a circuit length of 10cm was formed, and the transmission characteristics were evaluated. Use the network analyzer N5227B manufactured by Keysight Technology to transmit high-frequency signals, and measure the transmission loss at 20GHz. The obtained results are shown in Table 1 and Table 2.

(Warping Evaluation) The upper and lower copper foils of the copper-clad laminates with a thickness of 0.1 mm obtained in each example and each comparative example were processed by a laser processing machine, and predetermined holes were formed by electroless copper plating. Next, the wiring pattern is etched to form a conductive layer to obtain a panel of the substrate (size: 500mm×400mm). Next, measure the total amount of warping at four corners of the panel with a metal ruler, and use the average value as "warping". The obtained results are shown in Table 1, Table 2, and Fig. 3 .

[Table 1] Example 1 Example 2 Example 3 Example 4 Example 5 Example 6 resin composition Maleimide compound BMI-2300 15 15 15 - - 10 MIR-5000 - - - 40 40 - Cyanate compound SNCN 35 35 35 - - 30 Terminal unsaturated group modified polyphenylene ether compound OPE-2St1200 10 10 10 - - 60 OPE-2St2200 10 10 10 35 35 Phenol Biphenyl Arane Type Epoxy Resin NC-3000-FH - - - - - - Naphthalene skeleton type epoxy resin HP-4032D - - - - - - Styrene-isoprene-styrene elastomer SEPTON2104 10 10 10 - - - Styrene-butadiene block copolymer TR2250 - - - 25 25 - α-Methylstyrene Polymer Kristalex 20 20 20 - - - Spherical silica SC2500MB 150 150 150 - - 100 Zinc octanoate - - - - - 0.1 glass cloth Thickness (μm) 32 19 14 14 9 32 type Low dielectric glass Low dielectric glass Low dielectric glass Low dielectric glass Low dielectric glass Low dielectric glass Ratio of resin composition volume% 87.6 92.1 95.1 95.1 96.7 87.6 Relative permittivity Dk 3.1 3.0 3.0 2.6 2.6 3.3 Dielectric loss tangent Df 0.002 0.002 0.002 0.002 0.002 0.004 SKEW(10GHz~20GHz) nsec 6.9×10 ^-4 5.3×10 ^-4 7.2×10 ^-4 7.0×10 ^-4 5.5×10 ^-4 6.9×10 ^-4 Transmission loss 20GHz dB/cm 0.25 0.25 0.25 0.23 0.23 0.32 warping mm 1.0 0.5 2.8 10.0 17.0 1.0

[Table 2] Comparative example 1 Comparative example 2 Comparative example 3 Comparative example 4 Comparative Example 5 Comparative example 6 resin composition Maleimide compound BMI-2300 15 15 15 15 - - MIR-5000 - - - - 40 - Cyanate compound SNCN 35 35 35 68 - 65 Terminal unsaturated group modified polyphenylene ether compound OPE-2St1200 10 10 10 10 - - OPE-2St2200 10 10 10 10 35 - Phenol Biphenyl Arane Type Epoxy Resin NC-3000-FH - - - - - 30 Naphthalene skeleton type epoxy resin HP-4032D - - - - - 5 Styrene-isoprene-styrene elastomer SEPTON2104 10 10 10 10 - - Styrene-butadiene block copolymer TR2250 - - - - 25 - α-Methylstyrene Polymer Kristalex 20 20 20 20 - - Spherical silica SC2500MB 150 150 150 150 - 100 Zinc octanoate - - - - - 0.1 glass cloth Thickness (μm) 80 49 43 - - 32 type Low dielectric glass Low dielectric glass Low dielectric glass - - E glass Ratio of resin composition volume% 69.3 78.8 80.9 100 100 87.6 Relative permittivity Dk 3.3 3.2 3.2 2.9 2.5 3.4 Dielectric loss tangent Df 0.002 0.002 0.002 0.002 0.002 0.010 SKEW(10GHz~20GHz) nsec 1.1×10 ^-3 8.6×10 ^-4 8.7×10 ^-4 6.5×10 ^-4 7.0×10 ^-4 7.3×10 ^-4 Transmission loss 20GHz dB/cm 0.28 0.26 0.28 0.25 0.23 0.48 warping mm 0.8 0.5 1.0 31.5 74.0 1.5

As shown in Tables 1 and 2 and Figures 1 to 3, it is clear that when the ratio of the resin composition to the total amount of the prepreg is 81% by volume or more, the SKEW can be reduced and the relative permittivity can be reduced. In addition, it was found that warpage can be sufficiently reduced when the ratio of the resin composition to the total amount of the prepreg is 98% by volume or less. That is, it was found that the ratio of the resin composition to the total amount of the prepreg is preferably in the range of 81% by volume or more and 98% by volume or less.

In addition, according to this embodiment, the relative permittivity of the prepreg at 10 GHz after curing can be made 3.3 or less, and the dielectric loss tangent of the prepreg after curing at 10 GHz can be made 0.004 or less.

none

[Fig. 1] is a graph showing the relationship between the ratio of the resin composition and the relative permittivity. [Fig. 2] is a graph showing the relationship between the ratio of the resin composition and SKEW. [Fig. 3] is a graph showing the relationship between the ratio of the resin composition and the warpage.

Claims (11)

A prepreg, which is impregnated or coated with a resin composition containing a thermosetting compound on a glass fiber substrate, and which is Relative to the total amount of the prepreg, the ratio of the resin composition is within the range of 81% by volume to 98% by volume, The relative permittivity at 10 GHz after hardening is 3.3 or less, and the dielectric loss tangent is 0.004 or less. The prepreg according to claim 1, wherein the glass fiber base material is selected from the group consisting of E glass, D glass, S glass, T glass, Q glass, L glass, NE glass, and HME glass At least one type of glass fiber. The prepreg according to claim 1, wherein the thermosetting compound contains terminal unsaturated group-modified polyphenylene ether. The prepreg according to claim 3, wherein the content of the terminally unsaturated group-modified polyphenylene ether is 1-70 parts by mass relative to 100 parts by mass of resin solids in the resin composition. The prepreg according to claim 1, wherein the thermosetting compound contains one or more species selected from the group consisting of maleimide compounds, cyanate compounds, epoxy compounds, and phenol compounds. The prepreg according to claim 1, wherein the resin composition further contains a thermoplastic elastomer. The prepreg according to claim 6, wherein the content of the thermoplastic elastomer is 1 to 45 parts by mass relative to 100 parts by mass of the resin solid content in the resin composition. The prepreg according to claim 1, wherein the resin composition further contains a filler. The prepreg according to Claim 8, wherein the content of the filler is 50 to 1600 parts by mass relative to 100 parts by mass of the resin solid content in the resin composition. A laminate comprising a cured product of the prepreg according to any one of Claims 1 to 9. A printed wiring board having an insulating layer and a conductor layer; the insulating layer is a cured product containing the prepreg according to any one of claims 1 to 9.

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