resin composition

Abstract

To provide a resin composition that yields a cured product with a low coefficient of linear thermal expansion and can suppress delamination due to fracture of the cured product; a method for producing the resin composition; a resin sheet containing the resin composition; a circuit board containing a cured product of the resin composition; and a semiconductor device containing the circuit board. [Solution] A resin composition comprising (A) an epoxy resin, (B) an active ester resin containing a radical polymerizable group, and (C) a resin containing an imide bond, wherein component (A) comprises (A-1) a liquid epoxy resin having a viscosity of 100 mPa·s or more at 25°C, and component (C) comprises at least one of (C-1) a maleimide resin and (C-2) a polyimide resin, and the total amount of components (C-1) and (C-2) is 6% by mass or more and 20% by mass or less with respect to 100% by mass of the resin components in the resin composition.

Description

[Technical Field]

[0001] This invention relates to resin compositions, and more particularly to resin sheets, circuit boards, and semiconductor devices. [Background technology]

[0002] Circuit boards, such as printed wiring boards, are widely used in various electronic devices. A known manufacturing method for circuit boards involves a build-up method in which insulating layers and conductive layers are alternately stacked on an inner layer substrate. The insulating layer is formed, for example, by a cured resin composition (Patent Documents 1 and 2). Specifically, a resin composition layer containing a resin composition is formed, and this resin composition layer is cured to form an insulating layer containing a cured resin composition. [Prior art documents] [Patent Documents]

[0003] [Patent Document 1] Patent No. 6992333 [Patent Document 2] Japanese Patent Publication No. 2021-161323 [Overview of the project] [Problems that the invention aims to solve]

[0004] In recent years, the need for miniaturization of electronic devices and components has led to a demand for finer and higher-density wiring on circuit boards. As wiring becomes finer and higher-density, reducing the warping of the insulating layer becomes even more important, and from the perspective of reducing the warping of the insulating layer, a small coefficient of linear thermal expansion (CTE) is required for the cured resin composition.

[0005] Furthermore, when forming the insulating layer, a resin composition containing epoxy resin and activated ester resin may be used. When forming the insulating layer using this resin composition, curing stress may remain after the resin composition has cured. If this stress remains, the cured product is more likely to break, and delamination of the insulating layer may occur as a result of the breakdown of the cured product.

[0006] The present invention has been made in view of the above, and aims to provide a resin composition that yields a cured product with a low coefficient of linear thermal expansion and can suppress delamination due to fracture of the cured product; a method for producing the resin composition; a resin sheet containing the resin composition; a circuit board containing a cured product of the resin composition; and a semiconductor device containing the circuit board. [Means for solving the problem]

[0007] The inventors diligently studied to solve the aforementioned problems. As a result, the inventors found that a resin composition comprising (A) an epoxy resin, (B) an active ester resin containing a radical polymerizable group, and (C) a resin containing an imide bond, wherein component (A) comprises (A-1) a liquid epoxy resin having a viscosity of 100 mPa·s or more at 25°C, and component (C) comprises at least one of (C-1) a maleimide resin and (C-2) a polyimide resin, and the total amount of components (C-1) and (C-2) is 6% by mass or more and 20% by mass or less relative to 100% by mass of the resin components in the resin composition, can solve the aforementioned problems, and thus completed the present invention. In other words, the present invention includes the following:

[0008] <1> A resin composition comprising (A) an epoxy resin, (B) an active ester resin containing a radical polymerizable group, and (C) a resin containing an imide bond, (A) Component comprises (A-1) a liquid epoxy resin having a viscosity of 100 mPa·s or more at 25°C. Component (C) comprises at least one of (C-1) maleimide resin and (C-2) polyimide resin, A resin composition in which the total amount of component (C-1) and component (C-2) is 6% by mass or more and 20% by mass or less, relative to 100% by mass of the resin components in the resin composition. <2> (A) Component further comprises (A-3) an epoxy resin that is solid at 25°C. <1> The resin composition described above. <3> (A-3) The content of component (A-3) is 10% by mass or more and 50% by mass or less, relative to 100% by mass of the resin components in the resin composition. <2> The resin composition described above. <4> (A-3) The content of component is 25% by mass or more relative to 100% by mass of the resin components in the resin composition. <2> or <3> The resin composition described above. <5> The content of component (A-1) relative to 100% by mass of the resin component in the resin composition is M A1 [As mass%], the content of component (A-3) is M A3 When expressed as [mass %], the mass ratio M A3 / M A1 However, it is between 1.5 and 10. <2> ~ <4> A resin composition according to any one of the items. <6> (A-1) Component contains a liquid epoxy resin with an epoxy equivalent of 150 g / eq. or more. <1> ~ <5> A resin composition according to any one of the items. <7> (A-1) The content of component (A-1) is 3% by mass or more and 25% by mass or less, relative to 100% by mass of the resin components in the resin composition. <1> ~ <6> A resin composition according to any one of the items. <8> The content of component (A-1) is 15% by mass or less relative to 100% by mass of the resin components in the resin composition. <1> ~ <7> A resin composition according to any one of the items. <9> (B) The content of component (B) is 5% by mass or more and 40% by mass or less, relative to 100% by mass of the resin components in the resin composition. <1> ~ <8> A resin composition according to any one of the items. <10> The resin composition according to any one of <1> to <9>, wherein the component (B) contains a monovalent group represented by the following formula (B’). [Chemical formula] (In the formula (B’), Ar B1 represents a divalent aromatic group which may have a substituent; Ar B2 represents a monovalent aromatic group which may have a substituent; * represents a bonding site.) <11> The resin composition according to any one of <1> to <10>, wherein the component (B) contains at least one of an active ester compound represented by the following formula (B-i) and an active ester compound represented by the following formula (B-ii). [Chemical formula] (In the formula (B-i) and the formula (B-ii), Ar 11 each independently represents a monovalent aromatic group which may have a substituent; Ar 12 each independently represents a divalent aromatic group which may have a substituent; R 11 each independently represents a divalent group composed of a divalent aromatic group which may have a substituent, a divalent aliphatic group which may have a substituent, an oxygen atom, a sulfur atom, or a combination thereof; Ar 11 Ar 12 and R 11 at least one of them has a substituent containing a radically polymerizable group; m1, n1, m2 and n2 each independently represent an integer of 0 or more.) <12> The resin composition according to any one of <1> to <11>, wherein the component (B) contains an active ester compound containing a structure represented by the following formula (B-iv-a). [Chemical formula] (In equation (B-iv-a), Ring Ar 40 represents an aromatic ring which may have substituents; R 40 This represents a monovalent group selected from a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, and an alkenyl group having 1 to 8 carbon atoms; L represents a single bond or a divalent non-aromatic group that does not contain a tetrahydrodicyclopentadiene ring. <13> (A-1) The epoxy equivalent of component is 150 g / eq. or more and 5,000 g / eq. or less. (B) The active ester group equivalent of component is 120 g / eq. or more and 1,000 g / eq. or less. <1> ~ <12> A resin composition according to any one of the items. <14> Component (C) contains component (C-1), The content of component (C-1) is more than 30% by mass relative to the total amount of components (A-1) and (B) (100% by mass). <1> ~ <13> A resin composition according to any one of the items. <15> Component (C) contains component (C-1), (A-1) The epoxy equivalent of component is 150 g / eq. or more and 5,000 g / eq. or less. (B) The active ester group equivalent of component is 120 g / eq. or more and 1,000 g / eq. or less. (C-1) The maleimide group equivalent of component is 50 g / eq. to 2,000 g / eq. <1> ~ <14> A resin composition according to any one of the items. <16> The resin composition further comprises (D) other thermosetting resins. <1> ~ <15> A resin composition according to any one of the items. <17> (D) Other thermosetting resins include active ester resins that do not contain radical polymerizable groups, The aforementioned active ester resin that does not contain radical polymerizable groups contains an active ester compound represented by the following formula (D-2): <16> The resin composition described above. [ka] (In formula (D-2), Ar 61 Each of these independently represents a monovalent aromatic group which may have substituents; Ar 62 Each of these independently represents a divalent aromatic group which may have substituents; R 61 Each of these independently represents a divalent hydrocarbon group which may have substituents; Ar 61 Ar 62 and R 61 None of these contain radical polymerizable groups; n 61 (This represents an integer greater than or equal to 0.) <18> The resin composition further comprises (E) an inorganic filler. <1> ~ <17> A resin composition according to any one of the items. <19> The total amount of component (C-1) and component (C-2) is 2% by mass or more and 7% by mass or less relative to 100% by mass of nonvolatile components in the resin composition. <18> The resin composition described above. <20> (E) The content of component is 65% by mass or more relative to 100% by mass of nonvolatile components in the resin composition. <18> or <19> The resin composition described above. <21> (E) Component may include (E-1) a carbon-containing inorganic filler whose surface is treated with a surface treatment agent, or it may not include such a component. The carbon content of component (E-1) is 0.1% by mass or more relative to 100% by mass of the total amount of component (E-1). The carbon content of component (E-1) does not include the amount of carbon atoms that the surface treatment agent may contain. The content of component (E-1) is less than 10% by mass relative to 100% by mass of nonvolatile components in the resin composition. <18> ~ <20> A resin composition according to any one of the items. <22> Excluding resin compositions containing the compound represented by the following formula (Bv), <1> ~ <21> A resin composition according to any one of the items. [ka] (In equation (Bv), X 51 This represents a divalent group containing an aromatic ring substituted with at least one alkenyl group; Z 51 Each of these independently represents either a hydrogen atom or an acyl group having a hydrocarbon group with 1 to 20 carbon atoms; At least 1 Z 51 However, it is an acyl group having a hydrocarbon group with 1 to 20 carbon atoms. <23> Excluding resin compositions containing phenoxy resins represented by the following formula (H-1) and having a weight-average molecular weight of 10,000 to 200,000 on a polyethylene oxide basis, <1> ~ <22> A resin composition according to any one of the items. [ka] (In formula (H-1), X 81 Each of these independently represents a divalent group containing an aromatic ring substituted with at least one alkenyl group; Y 81 Each of these independently represents a hydrogen atom, an acyl group with 2 to 21 carbon atoms, or a glycidyl group; Z 81 Each of these independently represents a hydrogen atom or an acyl group with 2 to 21 carbon atoms, and all Z 81 More than 5 mole% of the composition consists of acyl groups with 2 to 21 carbon atoms; The number of carbon atoms in an acyl group includes the carbon atoms of the carbonyl group that makes up the acyl group; n 81 (This represents a repeating number, and its average value is between 15 and 500.) <24> Excluding resin compositions containing the active ester compound represented by the following formula (D-3), <1> ~ <23> A resin composition according to any one of the items. [ka] (In formula (D-3), n 71 Each of these independently represents an integer from 0 to 6; n 72 Each of these independently represents an integer from 1 to 5; n 73 Each of these independently represents an integer from 1 to 6. <25> Excluding resin compositions containing aromatic diamine compounds that contain ether bonds in their molecules, <1> ~ <24> A resin composition according to any one of the items. <26> The reaction initiation temperature, based on differential scanning calorimetry, is 100°C or higher. <1> ~ <25> A resin composition according to any one of the items. <27> If the reaction initiation temperature based on differential scanning calorimetry is T1 (°C) and the reaction opening peak temperature based on differential scanning calorimetry is T2 (°C), then the temperature difference T2-T1 is 62°C or greater. <1> ~ <26> A resin composition according to any one of the items. <28> The process includes mixing component (A), component (B), and component (C). <1> ~ <27> A method for producing the resin composition described in any one of the items. <29> The first step involves reacting component (A-1) and component (B) to obtain a reactant having a weight-average molecular weight of 10,000 to 200,000 in terms of polyethylene oxide, The second step involves mixing the reactant obtained in the first step with component (C), Excluding manufacturing methods that include, <28> A method for producing the resin composition described above. <30> A support and a resin composition layer formed on the support, The resin composition layer <1> ~ <27> A resin sheet comprising the resin composition described in any one of the items. <31> <1> ~ <27> A circuit board comprising a cured product of the resin composition described in any one of the items. <32> <31> A semiconductor device including the circuit board described above. [Effects of the Invention]

[0009] According to the present invention, it is possible to provide a resin composition that yields a cured product with a low coefficient of linear thermal expansion and can suppress delamination due to fracture of the cured product; a method for producing the resin composition; a resin sheet containing the resin composition; a circuit board containing a cured product of the resin composition; and a semiconductor device containing the circuit board. [Modes for carrying out the invention]

[0010] The present invention will be described in detail below with reference to embodiments and examples. However, the present invention is not limited to the embodiments and examples described below, and can be modified and implemented as appropriate without departing from the scope of the claims and equivalents of the present invention.

[0011] The embodiments described herein may be used in combination with each other, regardless of expressions such as "preferred" or "more preferred." For example, the numerical range may be described using the upper and lower limits of each range, as well as a range combining the numerical values ​​of the examples.

[0012] In this specification, "non-volatile components" as used in reference to a resin composition refer to components of the resin composition other than the organic solvents described later. Furthermore, "resin components" as used in reference to a resin composition refer to components of the resin composition other than the inorganic fillers described later.

[0013] [Resin composition] The resin composition of the present invention comprises (A) an epoxy resin, (B) an active ester resin containing a radical polymerizable group, and (C) a resin containing an imide bond. Furthermore, the epoxy resin (A) comprises (A-1) a liquid epoxy resin having a viscosity of 100 mPa·s or more at 25°C, and the resin containing an imide bond (C) comprises at least one of (C-1) a maleimide resin and (C-2) a polyimide resin. In addition, the resin composition is characterized in that the total amount of component (C-1) and component (C-2) is 6% by mass or more and 20% by mass or less based on 100% by mass of the resin components in the resin composition. The resin composition of the present invention yields a cured product with a low coefficient of linear thermal expansion by combining component (A) (A-1) and component (B) and component (C) (C) in specific amounts of component (C-1) and / or component (C-2). Furthermore, the resin composition of the present invention, by including components (A-1) and (B) as component (A), and specific amounts of component (C-1) and / or component (C-2) as component (C), can suppress the residual curing stress during the curing of the resin composition, thereby suppressing delamination due to fracture of the cured resin composition.

[0014] The resin composition of the present invention may further contain any components in combination with components (A-1), (B), and (C-1) and / or (C-2). Examples of optional components include (A-2) a liquid epoxy resin having a viscosity of less than 100 mPa·s at 25°C, (A-3) a solid epoxy resin at 25°C, (D) other thermosetting resins, (E) inorganic fillers, (F) curing accelerators, (G) organic fillers, (H) thermoplastic resins, (G) other additives, and (I) organic solvents. Each component contained in the resin composition will be described in detail below.

[0015] <(A) Epoxy resin> The resin composition of the present invention comprises (A) epoxy resin as component (A). (A) epoxy resin may be used alone or in combination of two or more types.

[0016] (A) As the epoxy resin, a curable resin having an epoxy group may be used. Examples of epoxy resins include bixylenol type epoxy resin, bisphenol A type epoxy resin, bisphenol C type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, bisphenol AF type epoxy resin, dicyclopentadiene type epoxy resin, trisphenol type epoxy resin, naphthol novolac type epoxy resin, phenol novolac type epoxy resin, tert-butyl-catechol type epoxy resin, naphthalene type epoxy resin, naphthol type epoxy resin, anthracene type epoxy resin, glycidylamine type epoxy resin, Examples include glycidyl ester type epoxy resins, cresol novolac type epoxy resins, phenol aralkyl type epoxy resins, biphenyl type epoxy resins, linear aliphatic epoxy resins, epoxy resins having a butadiene structure, alicyclic epoxy resins, heterocyclic epoxy resins, spiroring-containing epoxy resins, cyclohexane type epoxy resins, cyclohexanedimethanol type epoxy resins, naphthylene ether type epoxy resins, trimethylol type epoxy resins, tetraphenylethane type epoxy resins, isocyanurate type epoxy resins, and phenolphthaleimidine type epoxy resins.

[0017] (A) The epoxy resin preferably contains an epoxy resin that contains two or more epoxy groups per molecule. The proportion of epoxy resin containing two or more epoxy groups per molecule, relative to 100% by mass of epoxy resin, is preferably 50% by mass or more, more preferably 60% by mass or more, even more preferably 70% by mass or more, and is usually 100% by mass or less.

[0018] (A) The epoxy equivalent of the epoxy resin is preferably 50 g / eq. or more, more preferably 80 g / eq. or more, even more preferably 110 g / eq. or more, preferably 5,000 g / eq. or less, more preferably 3,000 g / eq. or less, even more preferably 2,000 g / eq. or less, and even more preferably 1,000 g / eq. or less. When the epoxy equivalent of the epoxy resin is within the above range, the crosslinking density of the cured resin composition can result in a cured product with sufficient crosslinking density. The epoxy equivalent is the mass of epoxy resin containing one equivalent of epoxy groups. This epoxy equivalent can be measured according to JIS K7236.

[0019] (A) The weight-average molecular weight (Mw) of the epoxy resin is preferably 100 or more, more preferably 150 or more, even more preferably 200 or more, preferably 5,000 or less, more preferably 3,000 or less, and even more preferably 1,500 or less. The weight-average molecular weight of the epoxy resin is the weight-average molecular weight on a polystyrene basis measured by gel permeation chromatography (GPC).

[0020] In the resin composition, (A) epoxy resin includes (A-1) a liquid epoxy resin having a viscosity of 100 mPa·s or more at 25°C. In the following description, "liquid epoxy resin having a viscosity of 100 mPa·s or more at 25°C" may be referred to as "high-viscosity epoxy resin".

[0021] (A-1) The high-viscosity epoxy resin is liquid at 25°C. Furthermore, this (A-1) high-viscosity epoxy resin has a viscosity within a specific range at 25°C. The specific viscosity range of (A-1) high-viscosity epoxy resin at 25°C is 100 mPa·s or more, preferably 200 mPa·s or more, more preferably 500 mPa·s or more, even more preferably 750 mPa·s or more, even more preferably 1,000 mPa·s or more, 1,500 mPa·s or more, 2,000 mPa·s or more, 3,000 mPa·s or more, or 4,000 mPa·s or more. There is no particular upper limit to the viscosity of (A-1) high-viscosity epoxy resin at 25°C, and it can be, for example, 1,000 Pa·s or less, 500 Pa·s or less, 300 Pa·s or less, or 250 Pa·s or less. (A-1) When the high-viscosity epoxy resin has a viscosity within the above-mentioned preferred range at 25°C, residual curing stress in the cured product of the resin composition can be further suppressed, and thus delamination due to fracture of the cured product can be further suppressed.

[0022] (A-1) The viscosity of epoxy resins such as high-viscosity epoxy resins can be measured using an E-type viscometer (RE-25U manufactured by Toki Sangyo, using a 1° 34' × R24 cone rotor) at a temperature of 25°C and a rotation speed of 100 rpm. If the component to be measured for viscosity cannot be measured properly at a rotation speed of 100 rpm (for example, if the measured viscosity value exceeds the upper limit of the viscosity that can be measured at a rotation speed of 100 rpm), the upper limit of the measurable viscosity can be increased by reducing the rotation speed to a constant rotation speed such as 50 rpm, 20 rpm, 10 rpm, 5 rpm, 2.5 rpm, 1 rpm, or 0.5 rpm. In such a case, the viscosity value measured at the highest rotation speed among the changed rotation speeds can be used as the viscosity at a temperature of 25°C. For example, if viscosity cannot be measured correctly under conditions of 25°C and 100 rpm, but can be measured correctly when the rotation speed is changed to 50 rpm (if the measured viscosity value is below the upper limit of viscosity measurable under conditions of 50 rpm), then the viscosity value measured at 50 rpm can be considered the viscosity of the component at 25°C. Also, for example, if viscosity cannot be measured correctly under conditions of 25°C and 100 rpm, and cannot be measured correctly even when the rotation speed is changed to 50 rpm, 20 rpm, 10 rpm, and 5 rpm, but can be measured correctly when the rotation speed is changed to 2.5 rpm (if the measured viscosity value is below the upper limit of viscosity measurable under conditions of 2.5 rpm), then the viscosity value measured at 2.5 rpm can be considered the viscosity of the component at 25°C. Here, the upper limit of viscosity measurable under specific rotation speed conditions is an inherent value that is affected by the angle and diameter of the cone rotor in the E-type viscometer.

[0023] (A-1) The high-viscosity epoxy resin may contain one epoxy group per molecule, or it may contain two or more epoxy groups.

[0024] Furthermore, (A-1) the high viscosity epoxy resin is preferably one or more epoxy resins selected from the group consisting of bisphenol A type epoxy resin, bisphenol C type epoxy resin, bisphenol F type epoxy resin, bisphenol AF type epoxy resin, naphthalene type epoxy resin, glycidyl ester type epoxy resin, glycidylamine type epoxy resin, phenol novolac type epoxy resin, alicyclic epoxy resins such as alicyclic epoxy resins having an ester skeleton, cyclohexane type epoxy resin, cyclohexanedimethanol type epoxy resin, and epoxy resins having a butadiene structure.

[0025] (A-1) Specific examples of high-viscosity epoxy resins include DIC's "HP-4032," "HP-4032-D," and "HP-4032-SS" (naphthalene-type epoxy resin); Mitsubishi Chemical's "828US," "828EL," "825," and "Epicote 828EL" (bisphenol A-type epoxy resin); Mitsubishi Chemical's "807" and "1750" (bisphenol F-type epoxy resin); Mitsubishi Chemical's "152" (phenol novolac-type epoxy resin); and Mitsubishi Chemical's "630" and "630LSD" (glycidylamine-type epoxy resin). Examples include: "ZX-1059" (a mixture of bisphenol A type epoxy resin and bisphenol F type epoxy resin) manufactured by Nippon Steel Chemical & Material Co., Ltd.; "EX-721" (glycidyl ester type epoxy resin) manufactured by Nagase ChemteX Co., Ltd.; "Celoxide 2021P" (alicyclic epoxy resin with an ester skeleton) manufactured by Daicel Corporation; "PB-3600" (epoxy resin with a butadiene structure) manufactured by Daicel Corporation; and "ZX1658" and "ZX1658GS" (liquid 1,4-glycidylcyclohexane type epoxy resin) manufactured by Nippon Steel Chemical & Material Co., Ltd. (A-1) High viscosity epoxy resins may be used individually or in combination of two or more types.

[0026] (A-1) The epoxy equivalent of the high viscosity epoxy resin is preferably 150 g / eq. or more. Therefore, in a preferred embodiment, (A-1) the high viscosity epoxy resin includes a liquid epoxy resin with an epoxy equivalent of 150 g / eq. or more. (A-1) The epoxy equivalent of the high viscosity epoxy resin is more preferably 155 g / eq. or more, even more preferably 160 g / eq. or more, and even more preferably 165 g / eq. or more. (A-1) The upper limit of the epoxy equivalent of the high viscosity epoxy resin may be 5,000 g / eq. or less, 3,000 g / eq. or less, 1,500 g / eq. or less, 1,000 g / eq. or less, or 500 g / eq. or less, etc. (A-1) When the high viscosity epoxy resin has an epoxy equivalent within the above range, the rapid curing reaction of the resin composition can be suppressed, so that the residual curing stress during curing of the resin composition can be further suppressed, and delamination due to the fracture of the cured resin composition can be further suppressed.

[0027] From the viewpoint of significantly obtaining the desired effects of the present invention, the content of component (A-1) in the resin composition is preferably 10% by mass or more, more preferably 15% by mass or more, even more preferably 20% by mass or more, preferably 50% by mass or less, more preferably 45% by mass or less, even more preferably 40% by mass or less, and even more preferably 35% by mass or less, based on 100% by mass of component (A) in the resin composition.

[0028] From the viewpoint of significantly obtaining the desired effects of the present invention, the content of component (A-1) in the resin composition is preferably 5% by mass or more, more preferably 8% by mass or more, even more preferably 10% by mass or more, preferably 30% by mass or less, more preferably 25% by mass or less, and even more preferably 20% by mass or less, based on 100% by mass of the total of components (A), (B), and (C) in the resin composition.

[0029] From the viewpoint of significantly obtaining the desired effects of the present invention, the amount of component (A-1) in the resin composition is preferably 1% by mass or more, more preferably 3% by mass or more, even more preferably 5% by mass or more, even more preferably 7% by mass or more or 8% by mass or more, preferably 25% by mass or less, more preferably 20% by mass or less, even more preferably 15% by mass or less, and even more preferably 13% by mass or less, based on 100% by mass of the resin components in the resin composition. In particular, according to the embodiment in which the content of component (A-1) relative to 100% by mass of the resin components in the resin composition is 25% by mass or more (even more preferably 3% by mass or more), a cured product with a small coefficient of linear thermal expansion is obtained, and a resin composition that can suppress delamination due to fracture of the cured product is obtained, while at the same time, the occurrence of cracks after roughening treatment in the cured product of the resin composition is particularly easily suppressed, which is preferable.

[0030] From the viewpoint of significantly obtaining the desired effects of the present invention, the content of component (A-1) in the resin composition is preferably 0.5% by mass or more, more preferably 1% by mass or more, even more preferably 2% by mass or more, preferably 10% by mass or less, more preferably 7% by mass or less, and even more preferably 5% by mass or less, based on 100% by mass of the nonvolatile components in the resin composition.

[0031] In the resin composition, (A) epoxy resin may or may not contain (A-2) a liquid epoxy resin having a viscosity of less than 100 mPa·s at 25°C as component (A-2). In the following description, from the perspective of comparison with (A-1) high viscosity epoxy resin, "liquid epoxy resin having a viscosity of less than 100 mPa·s at 25°C" may be referred to as "low viscosity epoxy resin".

[0032] The content of (A-2) low viscosity epoxy resin in the resin composition is preferably 5% by mass or less, more preferably 3% by mass or less, and even more preferably 1% by mass or less, based on 100% by mass of non-volatile components in the resin composition. Since the resin composition does not have to contain (A-2) low viscosity epoxy resin, the lower limit of the content of such (A-2) low viscosity epoxy resin is, for example, 0% by mass or more, and may be 0% by mass. From the viewpoint of significantly obtaining the desired effects of the present invention, it is preferable that the resin composition does not contain (A-2) low viscosity epoxy resin.

[0033] The content of the (A-2) low viscosity epoxy resin in the resin composition is preferably 10% by mass or less, more preferably 5% by mass or less, even more preferably 3% by mass or less, and even more preferably 1% by mass or less, based on 100% by mass of the liquid epoxy resin in the resin composition (i.e., based on 100% by mass of the total of components (A-1) and (A-2)). Since the resin composition does not have to contain the (A-2) low viscosity epoxy resin, the lower limit of the content of such (A-2) low viscosity epoxy resin is, for example, 0% by mass or more, and may be 0% by mass.

[0034] In the resin composition, (A) epoxy resin may include (A-3) a solid epoxy resin at 25°C as component (A-3). In the following description, "a solid epoxy resin at 25°C" may be referred to as "solid epoxy resin".

[0035] (A-3) The solid epoxy resin is solid at 25°C. This (A-3) solid epoxy resin preferably has two or more epoxy groups per molecule, and more preferably has three or more epoxy groups per molecule. The range of the ratio of solid epoxy resin having two or more epoxy groups per molecule to 100% by mass of (A-3) solid epoxy resin is preferably 50% by mass or more, more preferably 60% by mass or more, and even more preferably 70% by mass or more.

[0036] The epoxy equivalent of component (A-3) may, in one embodiment, be the same as the epoxy equivalent of component (A) described above. That is, the epoxy equivalent of component (A-3) is preferably 50 g / eq. or more, more preferably 80 g / eq. or more, even more preferably 110 g / eq. or more, preferably 5,000 g / eq. or less, more preferably 3,000 g / eq. or less, even more preferably 2,000 g / eq. or less, and even more preferably 1,000 g / eq. or less. In particular, the epoxy equivalent of component (A-3) is even more preferably 150 g / eq. or more, and even more preferably 500 g / eq. or less or 500 g / eq. or less. When the epoxy equivalent of component (A-3) is within the above range, the occurrence of cracks after roughening treatment in the cured product of the resin composition can be further suppressed.

[0037] (A-3) From the viewpoint of obtaining a cured product with excellent heat resistance, the solid epoxy resin preferably contains an epoxy resin that contains an aromatic ring.

[0038] (A-3) Examples of solid epoxy resins include bixylenol-type epoxy resin, naphthalene-type epoxy resin, naphthalene-type tetrafunctional epoxy resin, naphthol novolac-type epoxy resin, naphthol aralkyl-type epoxy resin, cresol novolac-type epoxy resin, dicyclopentadiene-type epoxy resin, trisphenol-type epoxy resin, naphthol-type epoxy resin, biphenyl-type epoxy resin, naphthylene ether-type epoxy resin, anthracene-type epoxy resin, bisphenol A-type epoxy resin, bisphenol AF-type epoxy resin, phenol aralkyl-type epoxy resin, tetraphenylethane-type epoxy resin, phenolphthaleimidine-type epoxy resin, and monofunctional solid epoxy resins such as glycidyl stearate.

[0039] (A-3)Specific examples of solid epoxy resins include DIC's "HP4032H" (naphthalene-type epoxy resin); DIC's "HP-4700" and "HP-4710" (naphthalene-type tetrafunctional epoxy resins); DIC's "N-690" (cresol novolac-type epoxy resin); DIC's "N-695" (cresol novolac-type epoxy resin); DIC's "HP-7200", "HP-7200HH", "HP-7200H", and "HP-7200L" (dicyclopentadiene-type epoxy resins); and DIC's "EXA-7311" "EXA-7311-G3", "EXA-7311-G4", "EXA-7311-G4S", "HP-6000", "HP-6000L" (naphthylene ether type epoxy resin); "EPPN-502H" (trisphenol type epoxy resin) manufactured by Nippon Kayaku Co., Ltd.; "NC7000L" (naphthol novolac type epoxy resin) manufactured by Nippon Kayaku Co., Ltd.; "NC3000H", "NC3000", "NC3000L", "NC3000FH", "NC3100" (biphenyl type epoxy resin) manufactured by Nippon Steel Chemical & Material Co., Ltd.; "ESN41" manufactured by Nippon Steel Chemical & Material Co., Ltd. 00V (Naphthalene-type epoxy resin); "ESN475V" and "ESN485" (Naphthol-type epoxy resin) manufactured by Nippon Steel Chemical & Material Co., Ltd.; "ESN-4100VEK75" (Naphthol aralkyl-type epoxy resin) manufactured by Nippon Steel Chemical & Material Co., Ltd.; "ESN375" (Dihydroxynaphthalene-type epoxy resin) manufactured by Nippon Steel Chemical & Material Co., Ltd.; "YX4000H", "YX4000", "YX4000HK", and "YL7890" (Bixylenol-type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "YL6121" (Bifexylenol-type epoxy resin) manufactured by Mitsubishi Chemical Corporation. Nyl epoxy resin; Mitsubishi Chemical's "YX8800" (anthracene epoxy resin); Mitsubishi Chemical's "YX7700" (phenol aralkyl epoxy resin); Osaka Gas Chemical's "PG-100" and "CG-500"; Mitsubishi Chemical's "YL7760" (bisphenol AF epoxy resin); Mitsubishi Chemical's "YL7800" (fluorene epoxy resin); Mitsubishi Chemical's "1010" (bisphenol A epoxy resin); Mitsubishi Chemical's "1031S" (tetraphenylethane epoxy resin);Examples include "WHR-991S" (phenolphthaleimidine type epoxy resin) manufactured by Nippon Kayaku Co., Ltd., and glycidyl stearate manufactured by Tokyo Chemical Industry Co., Ltd. (A-3) Solid epoxy resins may be used individually or in combination of two or more types.

[0040] When the resin composition contains (A-3) a solid epoxy resin, the content of component (A-3) in the resin composition is preferably 40% by mass or more, more preferably 50% by mass or more, even more preferably 60% by mass or more or 65% by mass or more, preferably 90% by mass or less, more preferably 85% by mass or less, and even more preferably 80% by mass or less, based on 100% by mass of component (A) in the resin composition.

[0041] When the resin composition contains (A-3) a solid epoxy resin, the content of component (A-3) in the resin composition is preferably 10% by mass or more, more preferably 20% by mass or more, even more preferably 30% by mass or more or 35% by mass, preferably 60% by mass or less, more preferably 55% by mass or less, even more preferably 50% by mass or less or 46% by mass or less, based on 100% by mass of the total of components (A), (B), and (C) in the resin composition.

[0042] When the resin composition contains (A-3) a solid epoxy resin, the content of component (A-3) in the resin composition is preferably 10% by mass or more, more preferably 20% by mass or more, even more preferably 25% by mass or more, preferably 50% by mass or less, more preferably 45% by mass or less, even more preferably 40% by mass or less, or 36% by mass or less, based on 100% by mass of the resin components in the resin composition. In particular, according to the embodiment in which the content of component (A-3) is 25% by mass or more based on 100% by mass of the resin components in the resin composition, a cured product with a small coefficient of linear thermal expansion is obtained, and a resin composition that can suppress delamination due to fracture of the cured product is obtained, while at the same time, the occurrence of cracks after roughening treatment in the cured product of the resin composition is particularly easily suppressed, making it preferable.

[0043] When the resin composition contains (A-3) a solid epoxy resin, the content of component (A-3) in the resin composition is preferably 1% by mass or more, more preferably 3% by mass or more, even more preferably 5% by mass or more or 7% by mass or more, preferably 20% by mass or less, more preferably 15% by mass or less, and even more preferably 10% by mass or less, based on 100% by mass of the nonvolatile components in the resin composition.

[0044] If the resin composition contains (A-3) a solid epoxy resin, the content of component (A-3) relative to 100% by mass of the resin component in the resin composition is M A3 [Mass %]. Also, the content of component (A-1) relative to 100% mass of the resin component in the resin composition is M A1 [Mass %]. In this case, the mass ratio of component (A-3) to component (A-1) in the resin composition ([Content of component (A-3)] / [Content of component (A-1)]) is M A3 / M A1 It can be expressed as: Mass ratio M A3 / M A1 The mass ratio M is preferably 0.1 or higher, more preferably 0.5 or higher, even more preferably 1 or higher, even more preferably 1.5 or higher, and even more preferably 2 or higher, preferably 10 or lower, more preferably 7 or lower, even more preferably 5 or lower, and even more preferably 4 or lower. A3 / M A1 In embodiments where the coefficient of linear thermal expansion is 1.5 or higher, a resin composition is obtained that yields a cured product with a small coefficient of linear thermal expansion and can suppress delamination due to fracture of the cured product, while also being particularly effective in suppressing the occurrence of cracks after roughening treatment in the cured product of the resin composition, making it preferable.

[0045] From the viewpoint of significantly obtaining the desired effects of the present invention, the content of component (A) in the resin composition is preferably 20% by mass or more, more preferably 30% by mass or more, even more preferably 40% by mass or more or 45% by mass or more, preferably 70% by mass or less, more preferably 65% ​​by mass or less, and even more preferably 60% by mass or less, based on 100% by mass of the total of components (A), (B), and (C) in the resin composition.

[0046] From the viewpoint of significantly obtaining the desired effects of the present invention, the content of component (A) in the resin composition is preferably 10% by mass or more, more preferably 20% by mass or more, even more preferably 30% by mass or more, preferably 60% by mass or less, more preferably 50% by mass or less, and even more preferably 46% by mass or less, based on 100% by mass of the resin components in the resin composition.

[0047] From the viewpoint of significantly obtaining the desired effects of the present invention, the content of component (A) in the resin composition is preferably 5% by mass or more, more preferably 8% by mass or more, even more preferably 10% by mass or more, preferably 30% by mass or less, more preferably 20% by mass or less, and even more preferably 15% by mass or less, based on 100% by mass of the nonvolatile components in the resin composition.

[0048] <(B) Active ester resin containing radical polymerizable groups> The resin composition of the present invention comprises an active ester resin containing a radical polymerizable group (B) as component (B). The active ester resin containing a radical polymerizable group (B) does not include any component corresponding to component (A) as described above. The active ester resin containing a radical polymerizable group (B) may be used alone or in combination of two or more types.

[0049] Component (B) contains an active ester moiety in one molecule. The active ester moiety contained in component (B) is preferably an aromatic ester skeleton. An aromatic ester skeleton represents a skeleton having an ester bond and an aromatic ring attached to one or both ends of the ester bond. Among these, an aromatic ester skeleton having aromatic rings at both ends of the ester bond is preferred. Examples of groups having such a skeleton include arylcarbonyloxy group, aryloxycarbonyl group, arylenecarbonyloxy group, aryleneoxycarbonyl group, arylcarbonyloxyarylene group, arylenecarbonyloxyarylene group, aryleneoxycarbonylarylene group, heteroarylcarbonyloxy group, heteroaryloxycarbonyl group, heteroarylenecarbonyloxy group, heteroaryleneoxycarbonyl group, heteroaryloxyarylene group, heteroaryloxy Examples include cyclocarbonylarylene groups, heteroarylenecarbonyloxyarylene groups, heteroaryleneoxycarbonylarylene groups, heteroarylcarbonyloxyheteroarylene groups, heteroaryloxycarbonylheteroarylene groups, heteroarylenecarbonyloxyheteroarylene groups, heteroaryleneoxycarbonylheteroarylene groups, heteroaryleneoxycarbonylheteroarylene groups, arylcarbonyloxyheteroarylene groups, aryloxycarbonylheteroarylene groups, arylenecarbonyloxyheteroarylene groups, and aryleneoxycarbonylheteroarylene groups. Furthermore, the number of carbon atoms in a group having such a skeleton is preferably 7 to 20, more preferably 7 to 15, and even more preferably 7 to 11.

[0050] The aryl group is preferably one having 6 to 30 carbon atoms, more preferably one having 6 to 20 carbon atoms, and even more preferably one having 6 to 10 carbon atoms. Examples of such aryl groups include phenyl, 1-methylphenyl, naphthyl, and anthracenyl groups. Here, the naphthyl group is a concept that includes both 1-naphthyl and 2-naphthyl groups.

[0051] A heteroaryl group refers to a monovalent group formed by removing one hydrogen atom from an aromatic heterocycle, which has heteroatoms such as oxygen, nitrogen, and sulfur atoms in addition to carbon atoms as ring constituent atoms. Heteroaryl groups with 3 to 30 carbon atoms are preferred, those with 4 to 20 carbon atoms are more preferred, and those with 6 to 10 carbon atoms are even more preferred. Examples of such heteroaryl groups include furyl, thienyl, pyrrolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, imidazolyl, pyridyl, pyridadinyl, pyrimidinyl, pyrazinyl, and triazinyl groups (e.g., 1,3,5-triazine-2-yl).

[0052] The arylene group is preferably one having 6 to 30 carbon atoms, more preferably one having 6 to 20 carbon atoms, and even more preferably one having 6 to 10 carbon atoms. Examples of such arylene groups include phenylene, naphthylene, anthracenylene, and biphenylene (-C6H4-C6H4-). Here, the phenylene group is a concept that includes 1,2-phenylene, 1,3-phenylene, and 1,4-phenylene groups, and the naphthylene group is a concept that includes 1,2-naphthylene, 1,3-naphthylene, 1,4-naphthylene, 1,5-naphthylene, 1,6-naphthylene, 1,7-naphthylene, and 1,8-naphthylene groups.

[0053] The heteroarylene group means a divalent group formed by removing one hydrogen atom from an aromatic heterocyclic ring having, as ring-constituting atoms, in addition to carbon atoms, heteroatoms such as oxygen atoms, nitrogen atoms, sulfur atoms, etc. As the heteroarylene group, a heteroarylene group having 3 to 30 carbon atoms is preferable, a heteroarylene group having 4 to 20 carbon atoms is more preferable, and a heteroarylene group having 6 to 10 carbon atoms is even more preferable. Examples of such heteroarylene groups include a pyrrolediyl group, a furandiyl group, a thiophenediyl group, a pyridinediyl group, a pyridazinediyl group, a pyrimidinediyl group, a pyrazinediyl group, a triazinediyl group, a piperidinediyl group, a triazolediyl group, a purinediyl group, a carbazolediyl group, a quinolinediyl group, an isoquinolinediyl group, etc.

[0054] Aromatic ester skeletons, and aromatic groups such as aryl groups, arylene groups, heteroaryl groups, and heteroarylene groups may have substituents. There is no particular limitation on the substituents. For example, halogen atoms, -OH, -O-C 1-6 alkyl group, -N(C 1-10 alkyl group)2, an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an alkynyl group having 2 to 30 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, -NH2, -CN, -C(O)O-C 1-10 alkyl group, -COOH, -C(O)H, -NO2, substituents containing a radical polymerizable group, etc. Here, the term "C p-q "(p and q are each independently positive integers and satisfy p < q.) represents that the number of carbon atoms of the organic group described immediately after this term is p to q. For example, the expression "C 1-10 [[ID=​​​The term "aromatic group" refers to a group obtained by removing one or more hydrogen atoms from the aromatic ring of an aromatic compound. More specifically, a monovalent aromatic group is a group obtained by removing one hydrogen atom from the aromatic ring of an aromatic compound, and a divalent aromatic group is a group obtained by removing two hydrogen atoms from the aromatic ring of an aromatic compound. The term "aromatic ring" refers to a ring that obeys Hückel's rule, where the number of electrons in the π-electron system on the ring is 4n+2 (where n is an integer greater than or equal to 1), and includes monocyclic aromatic rings and fused polycyclic aromatic rings formed by the fusion of two or more monocyclic aromatic rings. An aromatic ring may be an aromatic carbocyclic ring having only carbon atoms as ring constituent atoms, or it may be an aromatic heterocyclic ring having carbon atoms and non-carbon atoms (for example, heteroatoms such as oxygen atoms, nitrogen atoms, and sulfur atoms) as ring constituent atoms.

[0056] (B) The number of active ester sites contained in one molecule of component is, for example, one or more, preferably two or more.

[0057] Component (B) contains a radical polymerizable group. A radical polymerizable group is a group containing a radically polymerizable ethylenically unsaturated bond. Ethylenelycol unsaturated bonds do not include reaction-inert unsaturated bonds that constitute aromatic groups such as benzene rings.

[0058] From the viewpoint of obtaining the desired effects of the present invention more significantly, it is preferable that component (B) contains a monovalent group represented by the following formula (B'). There are no particular restrictions on the position in which component (B) contains the monovalent group represented by the following formula (B'). In a preferred embodiment, component (B) may contain a monovalent group represented by the following formula (B') as a substituent.

[0059] [ka]

[0060] (In formula (B'), Ar B1 represents a divalent aromatic group which may have substituents; Ar B2represents a monovalent aromatic group which may have substituents; * indicates a binding site.

[0061] In equation (B'), Ar B1 represents a divalent aromatic group which may have substituents. Also, in formula (B'), Ar B2 represents a monovalent aromatic group which may have substituents. Here, Ar B1 and Ar B2 The aromatic rings that make up the compound may be aromatic carbocyclic rings or aromatic heterocyclic rings. That is, Ar B1 This may be an arylene group which may have substituents, or a heteroarylene group which may have substituents. B2 This may be an aryl group which may have substituents, or a heteroaryl group which may have substituents. In particular, Ar B1 It is preferable that it is an arylene group which may have substituents. Also, Ar B2 It is preferable that is an aryl group which may have substituents. Furthermore, Ar B1 is an arylene group which may have substituents, and Ar B2 It is more preferable that the group is an aryl group which may have substituents. B1 and Ar B2 The substituents that may be present are the same as those that may be present on the aromatic ester skeleton described above.

[0062] (B) Component includes (B-1) a resin containing a substituent with a radical polymerizable group and an active ester moiety, and (B-2) a resin containing a skeleton with a radical polymerizable group and an active ester moiety.

[0063] The terminal end of component (B-1) is preferably a monovalent aromatic group. An example of a monovalent aromatic group is an aryl group, as described above. Among these, a phenyl group is preferred as the monovalent aromatic group at the terminal end of component (B-1).

[0064] Component (B-1) may have a substituent containing a radical polymerizable group and an active ester moiety, as well as any of the following groups: an aromatic group, an aliphatic group, an oxygen atom, or a combination thereof.

[0065] (B-1) The aromatic group that component may have is preferably a divalent aromatic group, more preferably an arylene group or an aralkylene group, and even more preferably an arylene group. The arylene group is as described above. As for the aralkylene group, an aralkylene group having 7 to 30 carbon atoms is preferred, an aralkylene group having 7 to 20 carbon atoms is more preferred, and an aralkylene group having 7 to 15 carbon atoms is even more preferred. Among these, the phenylene group is preferred.

[0066] (B-1) The aliphatic groups that component may have are preferably divalent aliphatic groups, more preferably divalent saturated aliphatic groups, and even more preferably alkylene groups and cycloalkylene groups. The alkylene groups are preferably alkylene groups having 1 to 10 carbon atoms, more preferably alkylene groups having 1 to 6 carbon atoms, and even more preferably alkylene groups having 1 to 3 carbon atoms. Examples of alkylene groups include methylene groups, ethylene groups, propylene groups, 1-methylmethylene groups, 1,1-dimethylmethylene groups, 1-methylethylene groups, 1,1-dimethylethylene groups, 1,2-dimethylethylene groups, butylene groups, 1-methylpropylene groups, 2-methylpropylene groups, 1,1-dimethyl-3-methylpropylene groups, pentylene groups, hexylene groups, etc., with 1,1-dimethylmethylene groups being preferred.

[0067] The cycloalkylene group is preferably a cycloalkylene group having 3 to 20 carbon atoms, more preferably a cycloalkylene group having 3 to 15 carbon atoms, and even more preferably a cycloalkylene group having 5 to 10 carbon atoms. The cycloalkylene group may have a monocyclic or polycyclic structure. Examples of cycloalkylene groups include cyclopropylene, cyclobutylene, cyclopentylene, cyclohexylene, cyclopentylene, cycloheptylene, and cycloalkylene groups represented by the following formulas (a) to (d). In formulas (a) to (d), "*" represents a bond.

[0068] [ka]

[0069] (B-1) The "groups consisting of these combinations" that component (B-1) may have are preferably divalent groups, such as groups consisting of a combination of an aliphatic group and an aromatic group, or groups consisting of a combination of an aromatic group, an aliphatic group and another aromatic group. One embodiment of these groups consisting of these combinations is a group consisting of an arylene-alkylene-arylene combination, and a group consisting of a phenylene-1,1-dimethylmethylene-phenylene combination is preferred.

[0070] The aromatic and aliphatic groups that component (B-1) may have may further have substituents. These substituents are the same as those that the aromatic ester skeleton may have.

[0071] In component (B-1), examples of radical polymerizable groups include unsaturated hydrocarbon groups such as vinyl groups, propenyl groups (allyl group, 1-propenyl group, isopropenyl group), butenyl groups (1-butenyl group, clotyl group, methallyl group, isoclotyl group, etc.), pentenyl groups (1-pentenyl group, etc.), hexenyl groups (1-hexenyl group, etc.), heptenyl groups (1-heptenyl group, etc.), octenyl groups (1-octenyl group, etc.), cyclopentenyl groups (2-cyclopentenyl group, etc.), and cyclohexenyl groups (3-cyclohexenyl group, etc.); and α,β-unsaturated carbonyl groups such as acryloyl groups, methacryloyl groups, and maleimide groups (2,5-dihydro-2,5-dioxo-1H-pyrrole-1-yl group). In particular, component (B-1) preferably contains an allyl group as a substituent containing a radical polymerizable group.

[0072] The number of radical polymerizable groups per molecule of component (B-1) is preferably 1 or more, more preferably 2 or more, preferably 10 or less, more preferably 8 or less, and even more preferably 5 or less.

[0073] The "substituent containing a radical polymerizable group" contained in component (B-1) may be a substituent on a terminal monovalent aromatic group, or it may be a substituent on an aromatic group or an aliphatic group. When component (B-1) contains the "substituent containing a radical polymerizable group" as a substituent on a terminal monovalent aromatic group, it is preferable that component (B-1) contains the "substituent containing a radical polymerizable group" as substituents on aromatic groups at both ends.

[0074] In one preferred embodiment, component (B-1) preferably contains either an active ester compound represented by the following general formula (Bi) or an active ester compound represented by the following general formula (B-ii), and more preferably contains an active ester compound represented by the general formula (Bi).

[0075] [ka]

[0076] (In formulas (Bi) and (B-ii), Ar 11 Each of these independently represents a monovalent aromatic group which may have substituents; Ar 12 Each of these independently represents a divalent aromatic group which may have substituents; R 11 Each of these independently represents a divalent aromatic group which may have substituents, a divalent aliphatic group which may have substituents, an oxygen atom, a sulfur atom, or a divalent group which is a combination thereof; Ar 11 Ar 12 , and R 11 At least one of them has a substituent containing a radical polymerizable group; m1, n1, m2, and n2 each independently represent a non-negative integer.

[0077] In equations (Bi) and (B-ii), Ar 11 Each of these independently represents a monovalent aromatic group which may have substituents. The definitions of monovalent aromatic groups are as described above. The Ar in formulas (Bi) and (B-ii) 11 They may be the same or different from each other, but it is preferable that they be the same. Also, Ar 11 The group is preferably a phenyl group, a 1-naphthyl group, or a 2-naphthyl group, with a phenyl group or a 1-naphthyl group being more preferred.

[0078] Ar 11 The substituents that it may have are the same as those that the aromatic ester skeleton may have. Among them, Ar 11 If the compound has substituents, it is preferable that the substituents contain radical polymerizable groups.

[0079] In equations (Bi) and (B-ii), Ar 12 Each of these independently represents a divalent aromatic group which may have substituents. Divalent aromatic groups are as described above. Among them, Ar 12A phenylene group is preferred, and a 1,3-phenylene group is more preferred.

[0080] Ar 12 The substituents that it may have are the same as those that the aromatic ester skeleton may have. Among them, Ar 12 It is preferable that the compound has an aralkyl group as a substituent, and more preferably a benzyl group as a substituent.

[0081] In equations (Bi) and (B-ii), R 11 Each of these independently represents a divalent aromatic group which may have substituents, a divalent aliphatic group which may have substituents, an oxygen atom, a sulfur atom, or a divalent group which is a combination thereof. The divalent aromatic group is as described above.

[0082] R 11 The divalent aliphatic group represented by is preferably a divalent saturated aliphatic group, more preferably an alkylene group or a cycloalkylene group, and even more preferably a cycloalkylene group. The alkylene group and the cycloalkylene group are as described above.

[0083] R 11 The term "divalent group consisting of these combinations" refers to a divalent group consisting of a combination of a divalent aromatic group which may have substituents, a divalent aliphatic group which may have substituents, an oxygen atom, and / or a sulfur atom. Among these, R 11Preferably, the divalent group is a combination of these (i.e., a divalent group consisting of a combination of a divalent aromatic group which may have substituents, a divalent aliphatic group which may have substituents, an oxygen atom, and / or a sulfur atom). The divalent group is preferably a combination of a divalent aromatic group which may have substituents and a divalent aliphatic group which may have substituents, and more preferably a divalent group which alternates between a plurality of divalent aromatic groups which may have substituents and a plurality of divalent aliphatic groups which may have substituents. Specific examples of the divalent group include, for example, divalent groups represented by the following formulas (B1) to (B13), with (B10) and (B11) being particularly preferred. In the formulas, b1 to b9 represent integers from 0 to 10, preferably integers from 0 to 6, and more preferably integers from 0 to 5. In formulas (B1) to (B13), "*" represents a bond, and the wavy line represents the structure obtained by the reaction of the aromatic compound, the acid halide of the aromatic compound, or the esterified product of the aromatic compound used in the synthesis of component (B-1).

[0084] [ka]

[0085] [ka]

[0086] [ka]

[0087] [ka]

[0088] [ka]

[0089] R11 The substituents that may be present are the same as those that may be present on the aromatic ester skeleton.

[0090] In formula (Bi), m1 represents an integer greater than or equal to 0, preferably an integer between 0 and 10, more preferably an integer between 0 and 8, even more preferably an integer between 0 and 6, and even more preferably 0.

[0091] In equation (Bi), n1 represents an integer greater than or equal to 0, preferably an integer between 0 and 30, more preferably an integer between 3 and 30, and even more preferably an integer between 6 and 30.

[0092] In formula (B-ii), m2 and n2 each independently represent an integer greater than or equal to 0, preferably an integer between 0 and 20, more preferably an integer between 0 and 15, even more preferably an integer between 0 and 10, and even more preferably an integer between 0 and 6.

[0093] The active ester compound represented by formula (Bi) is preferably an active ester compound represented by the following general formula (Bia).

[0094] [ka]

[0095] (In the formula (Bia), Ar 21 Each of these independently represents a monovalent aromatic group having at least an allyl group as a substituent; Ar 22 Each of these independently represents a divalent aromatic group which may have substituents; R 21 Each of these independently represents a divalent aromatic group which may have substituents, a divalent aliphatic group which may have substituents, an oxygen atom, a sulfur atom, or a divalent group which is a combination thereof; m3 and n3 each independently represent a non-negative integer.

[0096] In formula (B-i-a), Ar[[ID=u4]] 21 each independently represents a monovalent aromatic group having at least an allyl group as a substituent. The monovalent aromatic group is as described above. Ar in formula (B-i-a) 21 may be the same as or different from each other, and is preferably the same. Ar 21 is preferably any one of a phenyl group, a 1-naphthyl group, and a 2-naphthyl group, more preferably a phenyl group or a 1-naphthyl group.

[0097] Ar 21 may have a substituent other than an allyl group. The substituent is the same as the substituent that the aromatic ester skeleton may have. <0​​​​​​​​​​​​​​​​​​​​​​​​​​​

[0103] (In formula (B-iv-a), ring Ar 40 represents an aromatic ring which may have substituents; R 40 represents a monovalent group selected from a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, and an alkenyl group having 1 to 8 carbon atoms; L represents a single bond or a divalent non-aromatic group not containing a tetrahydrodicyclopentadiene ring.)

[0104] In formula (B-iv-a), ring Ar 40 represents an aromatic ring which may have substituents. The term "aromatic ring" is as described above. Ring Ar 40 may be an aromatic carbocyclic ring or an aromatic heterocyclic ring, but an aromatic carbocyclic ring is preferred. Also, as ring Ar as an aromatic carbocyclic ring 40 specific examples include, for example, a benzene ring, a biphenyl ring, a naphthalene ring, and an anthracene ring. Among them, ring Ar 40 is preferably one or more aromatic carbocyclic rings selected from a benzene ring and a naphthalene ring, and more preferably a benzene ring.

[0105] Examples of the substituent that ring Ar 40 may have include, for example, a hydrocarbon group. The range of the number of carbon atoms of the hydrocarbon group as a substituent is preferably 1 to 12. Examples of the hydrocarbon group include an alkyl group having 1 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, and an allyl group. Here, the aryl group having 6 to 12 carbon atoms also includes a group in which a hydrocarbon group as a secondary substituent is substituted on the aromatic carbocyclic ring constituting the aryl group. In such a case, the number of carbon atoms of the hydrocarbon group as a secondary substituent is for ring Ar 40The number of carbon atoms in the aryl group, which may be a substituent, is included in the number of carbon atoms. Similarly, aralkyl groups with 7 to 12 carbon atoms also include groups in which a hydrocarbon group is substituted as a secondary substituent on the aromatic carbon ring constituting the aralkyl group. In such cases, the number of carbon atoms in the hydrocarbon group as a secondary substituent is the number of carbon atoms in the ring Ar 40 The carbon atoms of the aralkyl group as a substituent that may be present are included in the carbon number.Hereinafter, when a group containing an aromatic carbocyclic ring is given as a substituent, and the upper limit of the carbon atoms of the substituent is greater than the number of aromatic carbons constituting the aromatic carbocyclic ring, the substituent also includes embodiments in which a hydrocarbon group as a secondary substituent is substituted.In such cases, the carbon atoms of the hydrocarbon group as a secondary substituent are included in the carbon number of the substituent.As an example, a tolyl group can be treated as an aryl group with 7 carbon atoms.As another example, a trimethylbenzyl group can be treated as an aralkyl group with 10 carbon atoms.

[0106] Alkyl groups having 1 to 12 carbon atoms may be linear, branched, or cyclic. Specific examples of such alkyl groups include, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, methylbutyl, n-hexyl, methylpentyl, dimethylbutyl, n-heptyl, methylhexyl, dimethylpentyl, trimethylbutyl, ethylpentyl, n-octyl, isooctyl, methylheptyl, and dimethylhexyl groups. Examples include chain alkyl groups such as trimethylpentyl group, ethylhexyl group, ethylhexyl group, n-octyl group, n-nonyl group, n-decyl group, n-dodecyl group, and n-undecyl group; and cycloalkyl groups such as cyclopentyl group, cyclohexyl group, cycloheptyl group, methylcyclohexyl group, cyclooctyl group, methylcycloheptyl group, dimethylcyclohexyl group, methylcyclohexyl group, ethylcyclohexyl group, trimethylcyclohexyl group, cyclodecyl group, and cyclododecyl group.

[0107] Examples of aryl groups having 6 to 12 carbon atoms include phenyl, tolyl, xylyl, ethylphenyl, styryl, n-propylphenyl, isopropylphenyl, mesityl, ethinylphenyl, biphenyl (-C6H4-C6H5), naphthyl, and vinylnaphthyl groups.

[0108] Examples of aralkyl groups having 7 to 12 carbon atoms include benzyl group, α-methylbenzyl group, dimethylbenzyl group, trimethylbenzyl group, naphthylmethyl group, phenethyl group, and 2-phenylisopropyl group.

[0109] Other hydrocarbon groups include, for example, polycyclic structural groups such as indanyl, dicyclopentenyl, norbornyl, and decahydronaphthyl groups.

[0110] Ring Ar 40 The number of substituents that may be present is one or two or more. Ring Ar 40 If the compound has two or more substituents, those substituents may be the same or different.

[0111] Ring Ar 40 The ring may contain only the tetrahydrodicyclopentadiene ring and the oxy group (-O-) as explicitly shown in formula (B-iv-a). The tetrahydrodicyclopentadiene ring represents the ring shown in formula (B-iv-b) below. Also, the ring Ar 40 The ring may contain only the tetrahydrodicyclopentadiene ring and the oxy group (-O-) as explicitly shown in formula (B-iv-a), as well as the substituents mentioned above. Furthermore, the ring Ar 40 It may have a binding site that attaches to a structure other than the tetrahydrodicyclopentadiene ring and the oxy group (-O-) as explicitly shown in formula (B-iv-a), and the substituents mentioned above. Therefore, the ring Ar 40 It may be bound to other structures included in component (B-iv) (i.e., structures not shown in formula (B-iv-a)).

[0112] [ka]

[0113] In equation (B-iv-a), R 40 R represents a monovalent group selected from a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, and an alkenyl group having 1 to 8 carbon atoms. 40 Examples of alkyl groups having 1 to 8 carbon atoms in this context include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, and octyl groups. 40 Examples of alkenyl groups having 1 to 8 carbon atoms include vinyl, allyl, butenyl, pentenyl, hexenyl, heptenyl, and octenyl groups. Among these, R 40 The group is preferably a monovalent group selected from a hydrogen atom and an alkyl group having 1 to 8 carbon atoms, more preferably a monovalent group selected from a hydrogen atom and a methyl group, and even more preferably a hydrogen atom.

[0114] In formula (B-iv-a), L represents a single bond or a divalent non-aromatic group that does not contain a tetrahydrodicyclopentadiene ring. The term "divalent non-aromatic group" refers to a divalent group that does not contain an aromatic ring. Such a divalent non-aromatic group is preferably a divalent aliphatic hydrocarbon group, more preferably a divalent linear aliphatic hydrocarbon group, and even more preferably a linear alkylene group. The number of carbon atoms in such a linear alkylene group is preferably 1 to 12. Among these, L is preferably a single bond or a linear alkylene group, and more preferably a single bond.

[0115] The structure represented by formula (B-iv-a) may, for example, have a binding site on a tetrahydrodicyclopentadiene ring, and at this binding site, it may bind to other structures included in component (B-iv). Therefore, the structure represented by formula (B-iv-a) may be a monovalent group having a binding site on a tetrahydrodicyclopentadiene ring. The structure represented by formula (B-iv-a) may also have, for example, a ring Ar, not just a tetrahydrodicyclopentadiene ring. 40It also has binding sites, and at these multiple binding sites, it may bind to other structures included in component (B-iv). In the latter embodiment, the structure represented by formula (B-iv-a) is a tetrahydrodicyclopentadiene ring and an Ar ring. 40 It may be a divalent or more group having a binding site.

[0116] The position of the binding site on the tetrahydrodicyclopentadiene ring, and the relationship between the tetrahydrodicyclopentadiene ring and the Ar ring. 40 Focusing on the bonding site, examples of structures represented by formula (B-iv-a) may include those represented by formulas (B-iv-c1) to (B-iv-c6) below. Here, * represents a bonding site. The structure represented by formula (B-iv-a) may be any of these.

[0117] [ka]

[0118] [ka]

[0119] [ka]

[0120] The structure represented by formula (B-iv-a) is -CH2-CR from the tetrahydrodicyclopentadiene ring. 40 =Ring Ar between CH2 units 40 It has a bulky structure. From the viewpoint of significantly obtaining the desired effects of the present invention, it is preferable that the structure represented by formula (B-iv-a) has a large molecular weight. Specifically, the molecular weight of the structure represented by formula (B-iv-a) is preferably 264 or more, more preferably 279 or more, preferably 294 or more, preferably 600 or less, more preferably 500 or less, and even more preferably 400 or less.

[0121] Component (B-iv) preferably contains an active ester compound comprising a structural unit represented by the following formula (B-iv-d).

[0122] [ka]

[0123] (In formula (B-iv-d), Ring Ar 41 Each of these independently represents an aromatic ring which may have substituents; R 41 Each of these independently represents a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms; X 40 Each of these independently represents a binding site or a monovalent group represented by the following formula (X-1), and all X 40 1 mole% to 99 mole% of the mixture consists of monovalent groups represented by formula (X-1); n 40 (This represents a repeating number, and its average value is between 0.1 and 5.)

[0124] [ka]

[0125] (In formula (X-1), * indicates a binding site; R 40 and L are, respectively, R in equation (B-iv-a). 40 (And it is synonymous with L.)

[0126] In equation (B-iv-d), the ring Ar 41 Each of these independently represents an aromatic ring which may have substituents. Ring Ar 41 The ring Ar may be an aromatic carbon ring or an aromatic heterocycle, but an aromatic carbon ring is preferred. 41 Specific examples include, for instance, benzene rings, biphenyl rings, naphthalene rings, and anthracene rings. Among these, the Ar ring... 41Each of these is preferably one or more aromatic carbon rings independently selected from a benzene ring and a naphthalene ring, with a benzene ring being more preferred.

[0127] Ring Ar 41 Examples of substituents that may be present include hydrocarbon groups. The number of carbon atoms in the hydrocarbon group is preferably in the range of 1 to 12. Examples of hydrocarbon groups include alkyl groups with 1 to 12 carbon atoms, aryl groups with 6 to 12 carbon atoms, aralkyl groups with 7 to 12 carbon atoms, and allyl groups. An example of these hydrocarbon groups is, for example, the ring Ar in formula (B-iv-a) above. 40 The same examples as those described in "Substituents that may be present" can be cited. In particular, the ring Ar 41 The substituents that may be present are preferably one or more substituents selected from a methyl group, a phenyl group, a benzyl group, an α-methylbenzyl group, and a dicyclopentenyl group, with a methyl group being more preferred.

[0128] In equation (B-iv-d), R 41 Each of these independently represents either a hydrogen atom or a hydrocarbon group with 1 to 12 carbon atoms. 41 The hydrocarbon group in this is the ring Ar 41 Examples of substituents that may be present are the same hydrocarbon groups described above. In particular, R 41 Each of these groups is preferably one or more groups selected independently from a hydrogen atom, a methyl group, a phenyl group, a benzyl group, an α-methylbenzyl group, and a dicyclopentenyl group, and more preferably one or more groups selected from a hydrogen atom and a methyl group.

[0129] In equation (B-iv-d), X 40 Each of these independently represents a binding site or a monovalent group represented by formula (X-1). 40 When represents a bonding site, that bonding site can bond to a carbonyl group of another structural unit. For example, X 40The bonding site indicated by bonds to the carbonyl group of the polyarylcarbonyl unit. Furthermore, the monovalent group represented by formula (X-1) is preferably an allyl group. Also, in formula (B-iv-d), all X 40 The range of the proportion of monovalent groups represented by formula (X-1) is, for example, 1 mol% or more, preferably 10 mol% or more, more preferably 15 mol% or more, and for example, 99 mol% or less, preferably 80 mol% or less, and more preferably 60 mol% or less. In particular, when the monovalent group represented by formula (X-1) is an allyl group, all X 40 It is preferable that the proportion of allyl groups in the mixture falls within the aforementioned range.

[0130] In equation (B-iv-d), n 40 This represents the number of repetitions, and its average value is between 0.1 and 5. Specifically, n 40 n represents 0 or a number greater than 0. 40 The range of the average value (numerical mean) is, for example, 0.1 or more, preferably 0.2 or more, more preferably 0.5 or more, even more preferably 1 or more, 1.1 or more, or 1.2 or more, and for example, 5 or less, preferably 4 or less or less than 4, more preferably 3 or less or less than 3.

[0131] Component (B-iv) is more preferably an active ester compound containing a structural unit represented by the following formula (B-iv-e).

[0132] [ka]

[0133] (In formula (B-iv-e), R 42 Each of these independently represents a hydrocarbon group having 1 to 12 carbon atoms; R 43 Each of these independently represents a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms; X 41 Each of these independently represents a binding site or a monovalent group represented by the formula (X-1), and all X 411 mole% to 99 mole% of the mixture consists of monovalent groups represented by formula (X-1); n 41 This represents a repeating number, and its average value is between 0.1 and 5; Each h represents an independent integer between 0 and 3.

[0134] In equation (B-iv-e), R 42 Each of these independently represents a hydrocarbon group having 1 to 12 carbon atoms. Examples of hydrocarbon groups having 1 to 12 carbon atoms include alkyl groups having 1 to 12 carbon atoms, aryl groups having 6 to 12 carbon atoms, aralkyl groups having 7 to 12 carbon atoms, and allyl groups. An example of these hydrocarbon groups is, for example, the ring Ar in formula (B-iv-a) above. 40 The same examples as those described in "Substituents that may be present in R" can be given. In particular, R 42 Each of these groups is preferably a hydrocarbon group selected independently from a methyl group, a phenyl group, a benzyl group, an α-methylbenzyl group, and a dicyclopentenyl group, with a methyl group being more preferred. 42 The position in which the compound is bonded to the benzene ring shown in formula (B-iv-d) may be the ortho, meta, or para position relative to the oxy group (-O-), with the ortho position being preferred.

[0135] In equation (B-iv-e), R 43 Each of these independently represents a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms, and R in formula (B-iv-d) 41 This is synonymous with R. 43 In this, the hydrocarbon group having 1 to 12 carbon atoms is the R 42 The same examples as the hydrocarbon groups with 1 to 12 carbon atoms explained earlier can be cited. Among them, R 43 The group is preferably a monovalent group selected from a hydrogen atom, a methyl group, a phenyl group, a benzyl group, an α-methylbenzyl group, and a dicyclopentenyl group, and more preferably a monovalent group selected from a hydrogen atom and a methyl group.

[0136] In equation (B-iv-e), X 41Each of these independently represents a binding site or a monovalent group represented by formula (X-1), and X in formula (B-iv-d) 40 It is synonymous with X 41 When represents a bonding site, that bonding site can bond to a carbonyl group of another structural unit. For example, X 41 The bonding site indicated by bonds to the carbonyl group of the polyarylcarbonyl unit. Also, as mentioned above, the monovalent group represented by formula (X-1) is preferably an allyl group. Furthermore, in formula (B-iv-e), all X 41 The range of the proportion of monovalent groups represented by formula (X-1) is, for example, 1 mol% or more, preferably 10 mol% or more, more preferably 15 mol% or more, and for example, 99 mol% or less, preferably 80 mol% or less, and more preferably 60 mol% or less. In particular, when the monovalent group represented by formula (X-1) is an allyl group, all X 41 It is preferable that the proportion of allyl groups in the mixture falls within the aforementioned range.

[0137] In equation (B-iv-e), n 41 This represents the number of repetitions, and its average value is between 0.1 and 5. Specifically, n 41 This represents 0 or a number greater than 0. Specifically, n 41 n in equation (B-iv-d) 40 It represents the same number, and the range of its average value is also n 40 It can be the same as n. 41 The range of the average value (numerical mean) is, for example, 0.1 or more, preferably 0.2 or more, more preferably 0.5 or more, even more preferably 1 or more, 1.1 or more, or 1.2 or more, and for example, 5 or less, preferably 4 or less or less than 4, more preferably 3 or less or less than 3.

[0138] In equation (B-iv-e), h represents an integer between 0 and 3, independently of each other. More specifically, h is R 43 This represents the number of substitutions. h is preferably 1, 2, or 3, more preferably 1 or 2, and even more preferably 2. In particular, n in formula (B-iv-e) 41If i is less than 1, i is preferably 1, 2, or 3, and more preferably 2.

[0139] The structural unit represented by formula (B-iv-d) or formula (B-iv-e) may be a polyaryloxy unit as a structural unit derived from an aromatic hydroxy compound used as a raw material for component (B-iv). From the viewpoint of significantly obtaining the desired effects of the present invention, the range of the amount of the structural unit represented by formula (B-iv-d) relative to 100 mol% of the total amount of polyaryloxy units contained in component (B-iv) is preferably 20 mol% or more, more preferably 30 mol% or more, even more preferably 50 mol% or more, and usually 100 mol% or less. From a similar viewpoint, the range of the amount of the structural unit represented by formula (B-iv-e) relative to 100 mol% of the total amount of polyaryloxy units contained in component (B-iv) is preferably 20 mol% or more, more preferably 30 mol% or more, even more preferably 50 mol% or more, and usually 100 mol% or less.

[0140] Furthermore, if component (B-iv) contains any polyaryloxy unit represented by the following formula (B-iv-f), the total amount of the structural unit represented by formula (B-iv-e) and the structural unit represented by formula (B-iv-f) is preferably 30 mol% or more, more preferably 50 mol% or more, and usually 100 mol% or less, relative to 100 mol% of the total amount of polyaryloxy units contained in component (B-iv).

[0141] [ka]

[0142] (In formula (B-iv-f), m 41 This represents a repeating number, and its average value is between 1 and 5. * indicates a binding site.

[0143] In equation (B-iv-f), m 41 This represents a repeating number, and its average value is a number between 1 and 5. Among them, m41 The average value (numerical mean) is preferably 1 or greater than 1, preferably 4 or less than 4, more preferably 3 or less than 3, and even more preferably 2 or less than 2.

[0144] Component (B-iv) may contain any polyaryloxy unit other than the structural units described above. Examples of any polyaryloxy unit include the structural unit represented by the following formula (B-iv-g).

[0145] [ka]

[0146] (In formula (B-iv-f), Ar 42a Each of these independently represents one of the following: an optionally substituted benzene ring, an optionally substituted naphthalene ring, an optionally substituted biphenyl ring, an optionally substituted binaphthyl ring, and an optionally substituted fluorene ring; Ar 42b This represents a divalent hydrocarbon group having 1 to 10 carbon atoms, or a divalent group represented by the following formula (B-iv-h); m 40 This represents a repeating number, and its average value is a number between 1 and 5; r1 is either 1 or 2, independently of each other; * indicates a binding site.

[0147] [ka]

[0148] (In formula (B-iv-h), Ar 43Each of these independently represents one of the following: an optionally substituted benzene ring, an optionally substituted naphthalene ring, an optionally substituted biphenyl ring, an optionally substituted binaphthyl ring, and an optionally substituted fluorene ring; R 44 Each of these independently represents either a hydrogen atom or a hydrocarbon group having 1 to 8 carbon atoms; y1 and y2 each represent an integer greater than or equal to 1, independently of each other; * indicates a binding site.

[0149] In equation (B-iv-g), Ar 42a Each of these independently represents one of the following: an optionally substituted benzene ring, an optionally substituted naphthalene ring, an optionally substituted biphenyl ring, and an optionally substituted fluorene ring. Substituents for these rings include alkyl groups having 1 to 10 carbon atoms, alkoxy groups having 1 to 10 carbon atoms, aryl groups having 6 to 11 carbon atoms, aralkyl groups having 7 to 12 carbon atoms, aryloxy groups having 6 to 11 carbon atoms, and aralkyloxy groups having 7 to 12 carbon atoms.

[0150] Ar 42a In the substituents that may be present, the alkyl group having 1 to 10 carbon atoms may be linear, branched, or cyclic. Examples include methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group, isopropyl group, sec-butyl group, t-butyl group, isopentyl group, neopentyl group, t-pentyl group, isohexyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, methylcyclohexyl group, cyclooctyl group, dimethylcyclohexyl group, ethylcyclohexyl group, trimethylcyclohexyl group, cyclodecyl group, and the like.

[0151] Ar 42aIn the substituents that may be present, the alkoxy group having 1 to 10 carbon atoms may be linear, branched, or cyclic. Examples include methoxy, ethoxy, n-propoxy, n-butoxy, n-pentyloxy, n-hexyloxy, n-heptyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, isopropoxy, sec-butoxy, t-butoxy, isopentyloxy, neopentyloxy, t-pentyloxy, isohexyloxy, cyclopentyloxy, cyclohexyloxy, cycloheptyloxy, methylcyclohexyloxy, cyclooctyloxy, dimethylcyclohexyloxy, ethylcyclohexyloxy, trimethylcyclohexyloxy, and cyclodecyloxy groups.

[0152] Ar 42a Examples of substituents that may be present include aryl groups having 6 to 11 carbon atoms, or aryloxy groups having 6 to 11 carbon atoms. These include phenyl, tolyl, ethylphenyl, xylyl, propylphenyl, mesityl, naphthyl, methylnaphthyl, phenoxy, tolyloxy, ethylphenoxy, xyloxy, propylphenoxy, mesityloxy, naphthyloxy, and methylnaphthyloxy groups.

[0153] Ar 42a Examples of substituents that may be present include aralkyl groups having 7 to 12 carbon atoms, or aralkyloxy groups having 7 to 12 carbon atoms. These include benzyl group, methylbenzyl group, dimethylbenzyl group, trimethylbenzyl group, phenethyl group, 1-phenylethyl group, 2-phenylisopropyl group, naphthylmethyl group, benzyloxy group, methylbenzyloxy group, dimethylbenzyloxy group, trimethylbenzyloxy group, phenethyloxy group, 1-phenylethyloxy group, 2-phenylisopropyloxy group, naphthylmethyloxy group, and the like.

[0154] Among them, Ar 42aIt is preferable that the ring is a benzene ring, a naphthalene ring, or an aromatic ring in which these rings are substituted with a substituent selected from a methyl group and a 1-phenylethyl group. Here, the substituent selected from a methyl group and a 1-phenylethyl group is called "substituent S 4 This is what happens. In other words, Ar 42a is a benzene ring, substituent S 4 A benzene ring, a naphthalene ring, and a substituent S substituted with 4 It is preferable that the naphthalene ring is substituted with one of the following:

[0155] In equation (B-iv-g), Ar 42b This represents a divalent hydrocarbon group having 1 to 10 carbon atoms, or a divalent group represented by the formula (B-iv-h). 42b This corresponds to a linking group in a novolac or aralkyl structure. 42b Examples of divalent hydrocarbon groups having 1 to 10 carbon atoms include the methylene group and the tetrahydrodicyclopentadienylene group.

[0156] In equation (B-iv-h), Ar 43 Each of these independently represents one of the following: an optionally substituted benzene ring, an optionally substituted naphthalene ring, an optionally substituted biphenyl ring, and an optionally substituted fluorene ring. 43 Each of these independently represents Ar in equation (B-iv-g). 42a It is synonymous with Ar 43 The substituents that it may have include the Ar 42a Examples of substituents that can be present include Ar 43 These are, independently, a benzene ring and a substituent S. 4 A benzene ring, a naphthalene ring, and a substituent S substituted with 4 It is preferable that the naphthalene ring is substituted with one of the following:

[0157] In equation (B-iv-h), R 44Each of these independently represents either a hydrogen atom or a hydrocarbon group with 1 to 8 carbon atoms. 44 Examples of hydrocarbon groups having 1 to 8 carbon atoms that can be represented include alkyl groups and aryl groups. 44 The range of carbon atoms in the alkyl group is preferably 1 to 6. 44 The alkyl group in R may be linear, branched, or cyclic. 44 Examples of alkyl groups in R include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, t-butyl, pentyl, hexyl, and cyclohexyl groups. Among these, branched or cyclic alkyl groups are preferred. The number of carbon atoms in a chain alkyl group is preferably 1 to 4, and the number of carbon atoms in a cyclic alkyl group is preferably 6. Among these, R 44 The alkyl group in is preferably an alkyl group selected from methyl, isopropyl, isobutyl, t-butyl, and cyclohexyl groups, and more preferably an alkyl group selected from methyl, t-butyl, and cyclohexyl groups. 44 The range of carbon atoms in the aryl group is, for example, 6 or more, preferably 8 or less, more preferably 7 or less, and even more preferably 6. 44 Each of these is preferably a monovalent group selected independently from a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, and an aryl group having 6 to 7 carbon atoms; more preferably a monovalent group selected from a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, and a phenyl group; and even more preferably a monovalent group selected from a hydrogen atom and an alkyl group having 1 to 3 carbon atoms.

[0158] In formula (B-iv-h), each y1 independently represents an integer of 1 or more, preferably an integer between 1 and 5, and more preferably 1, 2, or 3. In formula (B-iv-h), each y2 independently represents an integer of 1 or more. In one embodiment, each y2 independently is preferably 1, 2, or 3, and more preferably 1 or 2.

[0159] Examples of divalent groups represented by formula (B-iv-h) include -CH2-Ph-CH2-, -CH2-Ph-Ph-CH2-, -CH2-Ph-CH2-Ph-CH2-, -CH2-Ph-C(CH3)2-Ph-CH2-, -CH2-Ph-CH(CH3)-Ph-CH2-, -CH2-Ph-CH(C6H5)-Ph-CH2-, -CH2-Ph-Flu-Ph-CH2-, -CH2-Np-CH2-, -CH2-Np-Np-CH2-, -CH2-Np-CH2-Np-CH2-, and -CH2-Np-Flu-Np-CH2-. Here, "Ph" represents the phenylene group (-C6H4-) and "Np" represents the naphthylene group (-C6H4-). 10 H6-) represents the fluorenyl group (-C 13 The H8- group is represented by "Ph-Ph", where "Ph-Np" represents a biphenylene group and "Np-Np" represents a binaphthyl group. These aromatic rings (Ph, Np, and Flu) may further have substituents such as alkyl groups having 1 to 6 carbon atoms, alkoxy groups having 1 to 6 carbon atoms, aryl groups having 6 to 12 carbon atoms, aryloxy groups having 6 to 12 carbon atoms, aralkyl groups having 7 to 12 carbon atoms, and aralkyloxy groups having 7 to 12 carbon atoms. The sum of the carbon atoms of the substituents is preferably 6 to 50, and more preferably 6 to 20. The divalent group represented by formula (B-iv-h) is preferably a divalent group selected from -CH2-Ph-CH2-, -CH2-Ph-Ph-CH2-, and -CH2-Np-CH2-, which are unsubstituted, alkyl-substituted, alkoxy-substituted, or phenyl-substituted, and more preferably a divalent group selected from -CH2-Ph-CH2- and -CH2-Ph-Ph-CH2-, which are unsubstituted, alkyl-substituted, alkoxy-substituted, or phenyl-substituted.

[0160] In equation (B-iv-g), m 40 This represents the number of repetitions, and its average value is a number between 1 and 5. Specifically, m 40 m in equation (B-iv-e) 41 It is synonymous with m. 40The average value (numerical mean) is preferably 1 or greater than 1, preferably 4 or less than 4, more preferably 3 or less than 3, and even more preferably 2 or less than 2.

[0161] In equation (B-iv-g), r1 is independently either 1 or 2. More specifically, r1 is Ar 42a This corresponds to the number of oxy groups bonded to it.

[0162] An example of any polyaryloxy unit represented by formula (B-iv-g) is the structural unit represented by formula (B-iv-f) mentioned above.

[0163] Furthermore, an example of an arbitrary polyaryloxy unit is the structural unit represented by the following formula (B-iv-j).

[0164] [ka]

[0165] (In formula (B-iv-j), Ar 44 Each of these independently represents one of the following: an optionally substituted benzene ring, an optionally substituted naphthalene ring, an optionally substituted biphenyl ring, an optionally substituted binaphthyl ring, and an optionally substituted fluorene ring; R 45 Each of these independently represents a single bond or a divalent group selected from hydrocarbon groups having 1 to 20 carbon atoms, -CO-, -O-, -S-, -SO2-, and -C(CF3)2-; k1 represents an integer between 0 and 3; * indicates a binding site.

[0166] In equation (B-iv-j), Ar 44Each of these independently represents one of the following: an optionally substituted benzene ring, an optionally substituted naphthalene ring, an optionally substituted biphenyl ring, an optionally substituted binaphthyl ring, and an optionally substituted fluorene ring. 44 Each of these independently represents Ar in equation (B-iv-g). 42a It is synonymous with Ar 44 The substituents that it may have include the Ar 42a Examples of substituents that can be present include Ar 44 These are, independently, a benzene ring and a substituent S. 4 A benzene ring, a naphthalene ring, and a substituent S substituted with 4 It is preferable that the naphthalene ring is substituted with one of the following:

[0167] In equation (B-iv-j), R 45Each of these independently represents a single bond or a divalent group selected from hydrocarbon groups having 1 to 20 carbon atoms, -CO-, -O-, -S-, -SO2-, and -C(CF3)2-. Examples of hydrocarbon groups having 1 to 20 carbon atoms include -CH2-, -CH(CH3)-, -C2H4-, -C(CH3)2-, cyclohexylene group, methylcyclohexylene group, dimethylcyclohexylene group, methylisopropylcyclohexylene group, cyclohexylcyclohexylene group, cyclohexyllidene group, methylcyclohexyllidene group, dimethylcyclohexyllidene group, trimethylcyclohexyllidene group, tetramethylcyclohexyllidene group, ethylcyclohexyllidene group, isopropylcyclohexyllidene group, t-butylcyclohexyllidene group, phenylcyclohexyllidene group, cyclohexylcyclohexyllidene group, (methylcyclohexyl)cyclohexyllidene group, (ethyl cyclohexyl Examples include (chlorohexyl)cyclohexyllidene group, (phenylcyclohexyl)cyclohexyllidene group, cyclododecylene group, cyclopentylidene group, methylcyclopentylidene group, trimethylcyclopentylidene group, cyclooctylidene group, cyclododecyllidene group, 9H-fluorene-9,9-diyl group, bicyclo[4.4.0]decylidene group, bicyclohexanediyl group, phenylene group, xylylene group, phenylmethylene group, diphenylmethylene group, norbornylene group, adamantylene group, tetrahydrodicyclopentadienylene group, tetrahydrotricyclopentadienylene group, divalent groups having a norbornane structure, and divalent groups having a tetrahydrotricyclopentadiene structure. Among these, R 45 Each of these is preferably a single bond or a divalent group selected from -CH2-, -CH(CH3)-, -C(CH3)2-, -CO-, -O-, -S-, -SO2-, trimethylcyclohexylidene group, cyclooctylidene group, cyclododecylidene group, bicyclohexanediyl group, 9H-fluorene-9,9-diyl group, and phenylmethylene group.

[0168] In equation (B-iv-j), k1 represents an integer between 0 and 3, preferably 0 or 1.

[0169] Examples of any polyaryloxy unit represented by formula (B-iv-j) include the structural units represented by formulas (B-iv-k1) to (B-iv-k8) mentioned above.

[0170] [ka]

[0171] [ka]

[0172] [ka]

[0173] [ka]

[0174] (In formulas (B-iv-k1) to (B-iv-k8), R 46 Each of these independently represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryl group having 6 to 11 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, an aryloxy group having 6 to 11 carbon atoms, or an aralkyloxy group having 7 to 12 carbon atoms; p 40 Each of these independently represents an integer between 0 and 4; q 40 Each of these independently represents an integer from 0 to 6; * indicates a binding site; R 45 R in equation (B-iv-j) 45 (This is synonymous with...)

[0175] In equations (B-iv-k1) to (B-iv-k8), R 46Each of these independently represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryl group having 6 to 11 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, an aryloxy group having 6 to 11 carbon atoms, or an aralkyloxy group having 7 to 12 carbon atoms. 46 The group represented by formula (B-iv-g) is Ar 42a Examples of substituents that it may have include alkyl groups having 1 to 10 carbon atoms, alkoxy groups having 1 to 10 carbon atoms, aryl groups having 6 to 11 carbon atoms, aralkyl groups having 7 to 12 carbon atoms, aryloxy groups having 6 to 11 carbon atoms, and aralkyloxy groups having 7 to 12 carbon atoms.

[0176] Component (B-iv) preferably contains a group represented by the following formula (B-iv-m) at the end of its molecular chain. The group represented by formula (B-iv-m) corresponds to a monoaryloxy group. In this specification, the term "monoaryloxy group" includes a monoaralkyloxy group unless otherwise specified.

[0177] [ka]

[0178] (In formula (B-iv-m), Ar 45 Each of these independently represents one of the following: an optionally substituted benzene ring, an optionally substituted naphthalene ring, an optionally substituted biphenyl ring, an optionally substituted binaphthyl ring, and an optionally substituted fluorene ring; R 47 Each of these independently represents a single bond or a divalent group selected from -CH2-, -CH(CH3)-, -C(CH3)2-, -CO-, -O-, -S-, -SO2-, and -C(CF3)2-; R 48 represents a single bond, or a divalent group selected from -CH2-, -CH(CH3)-, -C(CH3)2-, and -C(CF3)2-; k2 represents an integer between 0 and 3; * indicates a binding site.

[0179] In equation (B-iv-m), Ar 45 Each of these independently represents one of the following: an optionally substituted benzene ring, an optionally substituted naphthalene ring, an optionally substituted biphenyl ring, an optionally substituted binaphthyl ring, and an optionally substituted fluorene ring. 45 Each of these independently represents Ar in equation (B-iv-g). 42a It is synonymous with Ar 45 The substituents that it may have include the Ar 42a Examples of substituents that can be present include Ar 45 These are, independently, a benzene ring and a substituent S. 4 A benzene ring, a naphthalene ring, and a substituent S substituted with 4 It is preferable that the naphthalene ring is substituted with one of the following:

[0180] In formula (B-iv-m), k2 represents an integer between 0 and 3, preferably 0 or 1.

[0181] An example of a group represented by formula (B-iv-m) is a monovalent group represented by a formula obtained by removing one of the oxy groups at both ends of the divalent group represented by formulas (B-iv-k1) to (B-iv-k8) above.

[0182] In one example, the amount of monoaryloxy groups such as the group represented by formula (B-iv-m) is preferably 1 mol% or more, more preferably 10 mol% or more, and even more preferably 20 mol% or more, and usually less than 100 mol%, relative to the total amount of aromatic hydroxy compounds used as raw materials for component (B-iv).

[0183] Component (B-iv) preferably further includes a structural unit represented by the following formula (B-iv-n). The structural unit represented by formula (B-iv-n) may be a polyarylcarbonyl unit as a structural unit derived from aromatic polycarboxylic acids and / or aromatic polycarboxylic acid halides as raw materials for component (B-iv). In component (B-iv), the oxy group of the polyaryloxy unit and the carbonyl group of the polyarylcarbonyl unit may be bonded to form an active ester group.

[0184] [ka]

[0185] (In formula (B-iv-n), Ar 46 Each of these independently represents one of the following: an optionally substituted benzene ring, an optionally substituted naphthalene ring, an optionally substituted biphenyl ring, and an optionally substituted fluorene ring; R 49 Each of these independently represents a single bond or a divalent group selected from hydrocarbon groups having 1 to 20 carbon atoms, -CO-, -O-, -S-, -SO2-, and -C(CF3)2-; k3 represents an integer between 0 and 3; * indicates a binding site.

[0186] In equation (B-iv-n), Ar 46 Each of these independently represents one of the following: an optionally substituted benzene ring, an optionally substituted naphthalene ring, an optionally substituted biphenyl ring, and an optionally substituted fluorene ring. 46 Each of these independently represents Ar in equation (B-iv-g). 42a It is synonymous with Ar 46 The substituents that it may have include the Ar 42a Examples of substituents that can be present include Ar 46 These are, independently, a benzene ring and a substituent S. 4A benzene ring, a naphthalene ring, and a substituent S substituted with 4 It is preferable that the naphthalene ring is substituted with one of the following:

[0187] In equation (B-iv-n), R 49 Each of these independently represents a single bond or a divalent group selected from hydrocarbon groups with 1 to 20 carbon atoms, -CO-, -O-, -S-, -SO2-, and -C(CF3)2-. 49 The hydrocarbon groups with 1 to 20 carbon atoms that can be represented are R in formula (B-iv-j). 45 It is synonymous with [the above].

[0188] In formula (B-iv-n), k3 represents an integer between 0 and 3, preferably 0 or 1.

[0189] An example of a structural unit represented by formula (B-iv-n) is a structural unit represented by formulas (B-iv-k1) to (B-iv-k8) above, in which the oxy groups at both ends of the divalent group are both replaced with carbonyl groups.

[0190] Component (B-iv) can be produced, for example, by a manufacturing method that includes a step of reacting an aromatic hydroxy compound with an aromatic carboxylic acid and / or an aromatic carboxylic acid halide. The aromatic hydroxy compound may include aromatic polyhydric hydroxy compounds and aromatic monohydroxy compounds. The aromatic carboxylic acid may also include aromatic polyhydric carboxylic acids and aromatic monocarboxylic acids. Furthermore, the aromatic carboxylic acid halide may include halides of aromatic polyhydric carboxylic acids and halides of aromatic monocarboxylic acids. The reaction may be carried out in the presence of an alkaline catalyst such as sodium hydroxide or potassium hydroxide. To give a specific example, component (B-iv), which contains the structural unit represented by formula (B-iv-a), can be produced by a manufacturing method that includes reacting an aromatic hydroxy compound represented by the following formula (B-iv-o) with an aromatic carboxylic acid and / or an aromatic carboxylic acid halide.

[0191] [ka]

[0192] (In formula (B-iv-o), X 42 Each of these independently represents a hydrogen atom or a monovalent group represented by formula (X-1), and all X 42 1 mole% to 99 mole% of the mixture consists of monovalent groups represented by formula (X-1); R 42 , R 43 , n 41 and h are R in equation (B-iv-d), respectively. 42 , R 43 , n 41 (And is synonymous with h.)

[0193] In equation (B-iv-o), X 42 Each of these independently represents a hydrogen atom or a monovalent group represented by formula (X-1). Furthermore, as mentioned above, the monovalent group represented by formula (X-1) is preferably an allyl group. Also, in formula (B-iv-o), all X 42 The range of the proportion of monovalent groups represented by formula (X-1) is, for example, 1 mol% or more, preferably 10 mol% or more, more preferably 15 mol% or more, and for example, 99 mol% or less, preferably 80 mol% or less, and more preferably 60 mol% or less. In particular, when the monovalent group represented by formula (X-1) is an allyl group, all X 42 It is preferable that the proportion of allyl groups in the mixture falls within the aforementioned range.

[0194] The aromatic hydroxy compound represented by formula (B-iv-o) can be produced by a method comprising the steps of: reacting a phenolic compound such as cresol, phenylphenol, benzylphenol, xylenol, diphenylphenol, or dibenzylphenol with dicyclopentadiene in the presence of a Lewis acid catalyst to obtain the aromatic hydroxy compound represented by formula (B-iv-p); and allylating 1 mol% to 99 mol% of the hydroxyl groups of the aromatic hydroxy compound represented by formula (B-iv-p) with an allylating agent such as an allyl halide or allyl acetate.

[0195] [ka]

[0196] (In formula (B-iv-p), u represents the repeating number, and its average value is a number between 0.1 and 5; R 42 and h are R in equation (B-iv-e), respectively. 42 (And is synonymous with h.)

[0197] In equation (B-iv-p), u represents a repeating number, and its mean value is between 0.1 and 5. Specifically, u represents 0 or a number greater than 0. The range of the mean value (number mean) of u is, for example, 0.1 or greater, preferably 0.2 or greater, more preferably 0.5 or greater, even more preferably 1 or greater, 1.1 or greater, or 1.2 or greater, and for example, 5 or less, preferably 4 or less or less than 4, more preferably 3 or less or less than 3.

[0198] The aromatic hydroxy compound used in the method for producing component (B-iv) may include an aromatic hydroxy compound represented by the following formula (B-iv-q). When the aromatic hydroxy compound represented by the following formula (B-iv-q) is used, component (B-iv) containing the structural unit represented by the above formula (B-iv-g) is obtained.

[0199] [ka]

[0200] (In formula (B-iv-q), Ar 42a Ar 42b , m 40 and r1 are, respectively, Ar in equation (B-iv-g) 42a Ar 42b , m 40 (And is synonymous with r1.)

[0201] Examples of aromatic hydroxy compounds represented by formula (B-iv-q) include, for example, phenol novolac resins (e.g., "Shonol BRG-555" manufactured by Aica Kogyo Co., Ltd.), cresol novolac resins (e.g., "DC-5" manufactured by Nippon Steel Chemical & Material Co., Ltd.), xylenol novolac resins, biphenol novolac resins, aromatically modified phenol novolac resins, naphthol novolac resins, and other novolac resins. Other examples of aromatic hydroxy compounds represented by formula (B-iv-q) include: reaction products of phenols and dicyclopentadiene (dicyclopentadiene-type phenol resins); reaction products of naphthols and dicyclopentadiene (dicyclopentadiene-type naphthol resins); reaction products of phenols and terpenes (terpene-type phenol resins); reaction products of naphthols and terpenes (terpene-type naphthol resins); condensates of phenols and / or naphthols and xylylene glycol (e.g., "SN-160", "SN-395", and "SN-485" from Nippon Steel Chemical & Material Co., Ltd.); condensates of phenols and / or naphthols and isopropenylacetophenone; reaction products of phenols and / or naphthols and divinylbenzene; condensates of phenols and / or naphthols and biphenyl-based crosslinking agents (e.g., "MEH-7851" from UBE Corporation).

[0202] The aromatic hydroxy compound used in the method for producing component (B-iv) may include an aromatic hydroxy compound represented by the following formula (B-iv-r). When the aromatic hydroxy compound represented by the following formula (B-iv-r) is used, component (B-iv) containing the structural unit represented by the above formula (B-iv-h) is obtained.

[0203] [ka]

[0204] (In formula (B-iv-r), Ar 44 , R 45 and k1 are, respectively, Ar in equation (B-iv-j) 44 , R 45 (And it is synonymous with k1.)

[0205] Examples of aromatic hydroxy compounds represented by formula (B-iv-r) include dihydroxybenzenes such as catechol, resorcinol, methylresorcinol, hydroquinone, monomethylhydroquinone, dimethylhydroquinone, trimethylhydroquinone, mono-t-butylhydroquinone, and di-t-butylhydroquinone; naphthalenediols such as naphthalenediol, methylnaphthalenediol, and methylmethoxynaphthalenediol; biphenols such as biphenol, dimethylbiphenol, and tetramethylbiphenol; and bisphenols such as bisphenol A, bisphenol F, bisphenol C, bisphenol K, bisphenol Z, bisphenol S, tetramethylbisphenol A, tetramethylbisphenol F, tetramethylbisphenol S, tetramethylbisphenol Z, dihydroxydiphenyl sulfide, 4,4'-thiobis(3-methyl-6-t-butylphenol), bisphenol fluorene, biscresol fluorene, and 9,9-bis(3,5-dimethyl-4-hydroxyphenyl)-9H-fluorene.

[0206] In the method for producing component (B-iv), a monohydroxy compound may be used. Examples of monohydroxy compounds that can be used in the method for producing component (B-iv) include the monohydroxy compound represented by the following formula (B-iv-s). When the monohydroxy compound represented by the following formula (B-iv-s) is used, component (A1) containing the group represented by the above formula (B-iv-m) is obtained.

[0207] [ka]

[0208] (In formula (B-iv-s), Ar 45 , R 47 , R 48 and k2 are, respectively, Ar in the above formula (B-iv-m) 45 , R 47 , R 48 (And it is synonymous with k2.)

[0209] Examples of monohydroxy compounds represented by formula (B-iv-s) include phenol, o-cresol, m-cresol, p-cresol, 3,5-xylenol, o-phenylphenol, p-phenylphenol, 2-benzylphenol, 4-benzylphenol, 4-(α-cumyl)phenol, octylphenol, α-naphthol, β-naphthol, benzyl alcohol, tolylmethanol, dimethylbenzyl alcohol, biphenylmethanol, benzylbenzyl alcohol, naphthylmethanol, and the like.

[0210] Examples of aromatic carboxylic acids that can be used in the production method of component (B-iv) include those represented by the following formula (B-iv-t). Examples of aromatic carboxylic acid halides that can be used in the production method of component (B-iv) include halogenated aromatic carboxylic acids represented by the following formula (B-iv-t). When these aromatic carboxylic acids and / or aromatic carboxylic acid halides are used, component (B-iv) containing the structural unit represented by the above formula (B-iv-n) is obtained.

[0211] [ka]

[0212] (In formula (B-iv-t), Ar 46 , R 49 and k3 are, respectively, Ar in equation (B-iv-n). 46 , R 49(And it is synonymous with k3.)

[0213] Examples of aromatic carboxylic acids represented by formula (B-iv-n) include phthalic acid, isophthalic acid, terephthalic acid, 1,4-naphthalenedicarboxylic acid, 2,3-naphthalenedicarboxylic acid, 2,6-naphthalenedicarboxylic acid, 1,6-naphthalenedicarboxylic acid, 2,7-naphthalenedicarboxylic acid, 4,4-biphenyldicarboxylic acid, 4,4'-methylenebisbenzoic acid, 4,4'-carbonylbisbenzoic acid, and 4,4'-isopropylidenedibenzoic acid.

[0214] In the method for producing component (B-iv), aromatic monocarboxylic acids and / or halides thereof may be used. Examples of aromatic monocarboxylic acids that can be used in the method for producing component (B-iv) include aromatic monocarboxylic acids represented by the following formula (B-iv-u). Examples of aromatic monocarboxylic acid halides that can be used in the method for producing component (B-iv) include halides of aromatic monocarboxylic acids represented by the following formula (B-iv-u).

[0215] [ka]

[0216] (In equation (B-iv-u), Ar 47 Each of these independently represents one of the following: an optionally substituted benzene ring, an optionally substituted naphthalene ring, an optionally substituted biphenyl ring, an optionally substituted binaphthyl ring, and an optionally substituted fluorene ring; R 50 Each of these independently represents a single bond or a divalent group selected from -CH2-, -CH(CH3)-, -C(CH3)2-, -CO-, -O-, -S-, -SO2-, and -C(CF3)2-; k4 represents an integer between 0 and 3.

[0217] In equation (B-iv-u), Ar47 Each of these independently represents one of the following: an optionally substituted benzene ring, an optionally substituted naphthalene ring, an optionally substituted biphenyl ring, and an optionally substituted fluorene ring. 47 Each of these independently represents Ar in equation (B-iv-g). 42a It is synonymous with Ar 46 The substituents that it may have include the Ar 42a Examples of substituents that can be present include Ar 47 These are, independently, a benzene ring and a substituent S. 4 A benzene ring, a naphthalene ring, and a substituent S substituted with 4 It is preferable that the naphthalene ring is substituted with one of the following:

[0218] In equation (B-iv-u), R 50 Each of these independently represents a single bond or a divalent group selected from hydrocarbon groups with 1 to 20 carbon atoms, -CO-, -O-, -S-, -SO2-, and -C(CF3)2-. 50 The hydrocarbon groups with 1 to 20 carbon atoms that can be represented are R in formula (B-iv-j). 45 It is synonymous with [the above].

[0219] In equation (B-iv-u), k3 represents an integer between 0 and 3, preferably 0 or 1.

[0220] Examples of aromatic monocarboxylic acids represented by formula (B-iv-u) include benzoic acid, 1-naphthalenecarboxylic acid, 2-naphthalenecarboxylic acid, and biphenylcarboxylic acid.

[0221] Specific examples of component (B-1) include compounds represented by the following formulas (B-1-i) to (B-1-xiii). Furthermore, specific examples of component (B-1) include compounds described in paragraphs 0068 to 0071 of International Publication No. 2018 / 235424, and compounds described in paragraphs 0113 to 0115 of International Publication No. 2018 / 235425. Compounds represented by formulas (B-1-v) to (B-1-xiii) correspond to component (B-iv) mentioned above. However, component (B-1) is not limited to these specific examples. In the formulas, a represents an integer from 0 to 6; s represents an integer greater than or equal to 0; r represents an integer from 1 to 10; and n and m represent integers greater than or equal to 0.

[0222] [ka]

[0223] [ka]

[0224] [ka]

[0225] [ka]

[0226] [ka]

[0227] [ka]

[0228] [ka]

[0229] Component (B-1) may be synthesized by known methods. Component (B-1) can be synthesized, for example, by the method described in International Publication No. 2018 / 235424 or International Publication No. 2018 / 235425. Component (B-1) can also be synthesized, for example, by the method described in Japanese Patent Publication No. 2025-34122. In one example, component (B-iv) as component (B-1) can be synthesized by the method for producing component (B-iv) described above.

[0230] In component (B-2), an example of a skeleton containing a radical polymerizable group is the butadiene skeleton. The butadiene skeleton represents the carbon skeleton contained in the butenediyl group. Here, the butenediyl group includes the 2-butene-1,4-diyl group and the 3-butene-1,2-diyl group (i.e., the vinylethylene group). The aforementioned 2-butene-1,4-diyl group may be in the cis or trans form. Hereinafter, a structure containing the butadiene skeleton may be appropriately referred to as the "butadiene structure". This butadiene structure includes the aforementioned 2-butene-1,4-diyl group and the 3-butene-1,2-diyl group, as well as groups in which the hydrogen atoms contained in these groups are substituted with substituents. Examples of substituents include halogen atoms; saturated aliphatic hydrocarbon groups such as alkyl groups and cycloalkyl groups; aromatic hydrocarbon groups such as aryl groups; hydrocarbon oxy groups such as alkoxy groups, cycloalkyloxy groups, and aryloxy groups.

[0231] Preferred examples of butadiene structures include those represented by the following formulas (B14) to (B15).

[0232] [ka]

[0233] (In equations (B14) and (B15), R b Each of these independently represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms; * represents a bonding site.

[0234] In equations (B14) and (B15), R b Each of these independently represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms. b The atom is preferably a hydrogen atom or a halogen atom, and more preferably a hydrogen atom.

[0235] In one embodiment, component (B-2) preferably includes a butadiene structure represented by formula (B14) as a structure having a butadiene skeleton. In such a preferred embodiment, component (B-2) may include only a butadiene structure represented by formula (B14) as a structure having a butadiene skeleton, or it may include a combination of a butadiene structure represented by formula (B14) and a butadiene structure represented by formula (B15).

[0236] In one embodiment, the number of butadiene structures contained in one molecule of component (B-2) is, for example, one or more, preferably two or more. In particular, it is more preferable that component (B-2) contains a polybutadiene structure in which two or more butadiene structures are bonded to each other.

[0237] The component (B-2) containing the butadiene skeleton is preferably an active ester compound represented by the following formula (B-iii).

[0238] [ka]

[0239] (In formula (B-iii), Ar 1 Each of these independently represents a monovalent aromatic group which may have substituents; Ar 2 Each of these independently represents a divalent aromatic group which may have substituents; R 1 Each of these independently represents a divalent aliphatic group which may have substituents; R 2 Each of these independently represents a butadiene structure; m4 and n4 each independently represent a non-negative integer.

[0240] In equation (B-iii), Ar 1 Each of these independently represents a monovalent aromatic group which may have substituents, and Ar in formula (Bi) 11 This is similar to the monovalent aromatic group represented by . In particular, Ar 1 A 1-methylphenyl group is preferred.

[0241] In equation (B-iii), Ar 2 Each of these independently represents a divalent aromatic group which may have substituents, and Ar in formula (Bi) 12 This is similar to the divalent aromatic group represented by .

[0242] In equation (B-iii), R 1 Each of these independently represents a divalent aliphatic group which may have substituents. 1 The divalent aliphatic group represented by may be linear, branched, or cyclic. 1 The number of carbon atoms in the divalent aliphatic group represented by is preferably 1 to 12, more preferably 1 to 6, and even more preferably 1 to 4. The number of carbon atoms in substituents is not included in this number. Examples of divalent aliphatic groups include alkylene groups and alkenylene groups.

[0243] R 1 The alkylene group represented by may be linear, branched, or cyclic. Specific examples of alkylene groups are as described above.

[0244] R 1 The alkenylene group represented by may be linear, branched, or cyclic. Examples of alkenylene groups include etenylene, propenylene, butenylene, pentenylene, hexenylene, cyclopropenylene, cyclobutenylene, cyclopentenylene, cyclohexenylene, norborneylene, and the like.

[0245] In equation (B-iii), R 2 Each of these independently represents a butadiene structure. The butadiene structure is as described above.

[0246] In formula (B-iii), m4 represents an integer greater than or equal to 0, preferably an integer between 0 and 10, more preferably an integer between 0 and 8, and even more preferably an integer between 0 and 6. Each n4 independently represents an integer greater than or equal to 0, preferably an integer greater than or equal to 1, more preferably an integer greater than or equal to 3, and even more preferably an integer greater than or equal to 6. The upper limit of n4 is preferably an integer less than or equal to 50, more preferably an integer less than or equal to 40, and even more preferably an integer less than or equal to 30.

[0247] Ar 1 A monovalent aromatic group represented by Ar 2 A divalent aromatic group represented by R 1 Each of the divalent aliphatic groups represented by may have substituents. These substituents are the same as those that may be present on the aromatic ester skeleton.

[0248] A specific example of the active ester compound represented by formula (B-iii) is the active ester compound represented by formula (B-iii-a) below. However, the component (B-2) is not limited to this specific example. Ar in formula (B-iii-a) 1 m4 and n4 are, respectively, Ar in equation (B-iii) 1 This is the same as m4 and n4.

[0249] [ka]

[0250] Component (B) preferably contains either component (B-1) or component (B-2). Therefore, component (B) preferably contains one or more active ester compounds selected from the active ester compounds represented by formula (Bi), the active ester compounds represented by formula (B-ii), the active ester compounds represented by formula (B-iv), and the active ester compounds represented by formula (B-iii). It is more preferable to contain one or more active ester compounds selected from the active ester compounds represented by formula (Bi), the active ester compounds represented by formula (B-ii), and the active ester compounds represented by formula (B-iv), and it is even more preferable to contain at least one of the active ester compounds represented by formula (Bi) and the active ester compounds represented by formula (B-ii).

[0251] In one embodiment, component (B) may or may not contain an active ester compound represented by the following formula (Bv). Hereinafter, the active ester compound represented by the following formula (Bv) may be referred to as "the compound represented by formula (Bv)" or "component (B-3)".

[0252] [ka]

[0253] (In equation (Bv), X 51 This represents a divalent group containing an aromatic ring substituted with at least one alkenyl group; Z 51 Each of these independently represents either a hydrogen atom or an acyl group having a hydrocarbon group with 1 to 20 carbon atoms; At least 1 Z 51 However, it is an acyl group having a hydrocarbon group with 1 to 20 carbon atoms.

[0254] In equation (Bv), X 51 X represents a divalent group containing an aromatic ring substituted with at least one alkenyl group. 51An aromatic ring contained in which at least one alkenyl group is substituted is sometimes called an "aromatic ring Bv". There is no particular limit to the number of alkenyl group substitutions in an aromatic ring Bv. In addition, an aromatic ring Bv may have further substituents other than alkenyl groups, as long as at least one alkenyl group is substituted. Examples of substituents other than alkenyl groups that an aromatic ring Bv may have include alkyl groups having 1 to 12 carbon atoms, alkoxy groups having 1 to 12 carbon atoms, aryl groups having 6 to 12 carbon atoms, and so on.

[0255] Examples of alkenyl groups that can be found in the aromatic ring Bv include alkenyl groups with 3 to 12 carbon atoms.

[0256] In equation (Bv), X 51 It may further contain components other than the aromatic ring Bv, insofar as it contains the aromatic ring Bv and forms a divalent group. In one embodiment, X 51 It consists of a group made up of an aromatic ring Bv and other divalent groups X 52 It may also contain other divalent groups X 52 There are no particular restrictions. X 52 This may be, for example, a divalent aromatic group which may have substituents other than an alkenyl group, a divalent aliphatic group which may have substituents, an oxygen atom (-O-), a sulfur atom (-S-), a carbonyl group (-CO-), a sulfinyl group (-SO-), a sulfonyl group (-SO2-), or a divalent group consisting of a combination thereof.

[0257] In equation (Bv), Z 51 Each of these independently represents either a hydrogen atom or an acyl group having a hydrocarbon group with 1 to 20 carbon atoms. Also, in formula (Bv), there is at least one Z. 51 However, it is an acyl group having a hydrocarbon group with 1 to 20 carbon atoms. 51 The acyl group possessed by can be a monovalent group in which a monovalent hydrocarbon group such as an alkyl group, aryl group, or aralkyl group is bonded to a carbonyl group (-CO-). 51The acyl group possessed by is preferably a monovalent group in which an alkyl group having 1 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, or an aralkyl group having 7 to 13 carbon atoms is bonded to the carbonyl group (-CO-). Also, Z 51 The number of carbon atoms in the acyl group is preferably 2 to 8. Here, the number of carbon atoms in the acyl group includes the carbon atoms of the carbonyl group that constitutes the acyl group. 51 The acyl group present is more preferably an acetyl group, a propanoyl group, a butanoyl group, a benzoyl group, or a methylbenzoyl group, with acetyl or benzoyl groups being even more preferred.

[0258] From the viewpoint of significantly obtaining the desired effects of the present invention, the content of component (B-3) in the resin composition is preferably 5% by mass or less, more preferably 3% by mass or less, and even more preferably 1% by mass or less, based on 100% by mass of nonvolatile components in the resin composition. The lower limit of the content of component (B-3) may be 0% by mass or greater than 0% by mass. In particular, from the viewpoint of obtaining the desired effects of the present invention more significantly, the lower limit of the content of component (B-3) is more preferably closer to 0% by mass, and even more preferably 0% by mass. That is, in one preferred embodiment, the resin composition of the present invention does not contain the compound represented by formula (Bv). In other words, in one preferred embodiment, the resin composition of the present invention excludes resin compositions containing the compound represented by formula (Bv).

[0259] The equivalent amount of the active ester group of component (B) is preferably 120 g / eq. or more, more preferably 150 g / eq. or more, even more preferably 200 g / eq. or more, 220 g / eq. or more, 240 g / eq. or more, or 250 g / eq. or more, and preferably 1,000 g / eq. or less, more preferably 600 g / eq. or less, and even more preferably 450 g / eq. or less. Here, the equivalent amount of the active ester group represents the mass of the active ester compound per equivalent of the active ester group.

[0260] From the viewpoint of significantly obtaining the desired effects of the present invention, in the resin composition of the present invention, (A-1) The epoxy equivalent of the high-viscosity epoxy resin is 150 g / eq. or more and 5,000 g / eq. or less. (B) The amount of active ester group equivalent in the active ester resin containing radical polymerizable groups is preferably 120 g / eq. to 1,000 g / eq.

[0261] The weight-average molecular weight (Mw) of component (B) is preferably 150 or more, more preferably 200 or more, even more preferably 250 or more, 450 or more, 500 or more, or 600 or more, preferably 3,000 or less, more preferably 2,000 or less, even more preferably 1,500 or less, or 1,000 or less. The weight-average molecular weight (Mw) of component (B) is the weight-average molecular weight on a polystyrene basis measured by gel permeation chromatography (GPC).

[0262] The ratio of component (A) to component (B) is the ratio of [total number of active ester groups of component (B)] / [total number of epoxy groups of component (A)], which is preferably 0.01 or more, more preferably 0.1 or more, even more preferably 0.3 or more, preferably 5 or less, more preferably 3 or less, and even more preferably 1 or less. Here, "total number of active ester groups of component (B)" is the value obtained by dividing the mass of each component (B) present in the resin composition by the equivalent amount of active ester groups of each component (B), and summing up all of these values. Also, "total number of epoxy groups of component (A)" is the value obtained by dividing the mass of each component (A) present in the resin composition by the equivalent amount of epoxy of each component (A), and summing up all of these values.

[0263] From the viewpoint of significantly obtaining the desired effects of the present invention, the content of component (B) in the resin composition is preferably 10% by mass or more, more preferably 15% by mass or more, even more preferably 20% by mass or more, preferably 50% by mass or less, more preferably 40% by mass or less, and even more preferably 35% by mass or less, based on 100% by mass of the total of components (A), (B), and (C) in the resin composition.

[0264] From the viewpoint of significantly obtaining the desired effects of the present invention, the content of component (B) in the resin composition is preferably 5% by mass or more, more preferably 10% by mass or more, even more preferably 15% by mass or more, preferably 40% by mass or less, more preferably 35% by mass or less, and even more preferably 30% by mass or less, based on 100% by mass of the resin components in the resin composition.

[0265] From the viewpoint of significantly obtaining the desired effects of the present invention, the content of component (B) in the resin composition is preferably 1% by mass or more, more preferably 3% by mass or more, even more preferably 5% by mass or more, preferably 20% by mass or less, more preferably 15% by mass or less, even more preferably 10% by mass or less, or 8% by mass or less, based on 100% by mass of the nonvolatile components in the resin composition.

[0266] The content of component (B) relative to 100% by mass of the resin component in the resin composition is M B When expressed as [mass %], the mass ratio of component (B) to component (A-1) in the resin composition ([content of component (B)] / [content of component (A-1)]) is M B / M A1 It can be expressed as: Mass ratio M B / M A1 From the viewpoint of significantly obtaining the desired effects of the present invention, the value is preferably 0.1 or higher, more preferably 0.5 or higher, even more preferably 1 or higher, even more preferably 1.5 or higher, preferably 10 or lower, more preferably 5 or lower, and even more preferably 3 or lower.

[0267] The content of component (A) relative to 100% by mass of the resin component in the resin composition is M A When expressed as [mass%], the mass ratio of component (B) to component (A) in the resin composition ([content of component (B)] / [content of component (A)]) is M B / M A It can be expressed as: Mass ratio M B / M AFrom the viewpoint of significantly obtaining the desired effects of the present invention, the value is preferably 0.01 or higher, more preferably 0.1 or higher, even more preferably 0.3 or higher, even more preferably 0.4 or higher, preferably 5 or lower, more preferably 3 or lower, even more preferably 1 or lower, and even more preferably 0.8 or lower.

[0268] <(C) Resin containing imide bonds> The resin composition of the present invention includes a resin containing an (C) imide bond as component (C). The resin containing the (C) imide bond does not include those corresponding to components (A) and (B) described above. The resin containing the (C) imide bond may be used alone or in combination of two or more types.

[0269] In the resin composition of the present invention, component (C) comprises at least one of (C-1) maleimide resin and (C-2) polyimide resin. Component (C) may consist only of (C-1) maleimide resin, only of (C-2) polyimide resin, or a combination of (C-1) maleimide resin and (C-2) polyimide resin. When the resin composition of the present invention contains only (C-1) maleimide resin as component (C), "total amount of (C-1) component and (C-2) component" should be read as "content of (C-1) component" when applying the invention. Furthermore, when the resin composition of the present invention contains only (C-2) polyimide resin as component (C), "total amount of (C-1) component and (C-2) component" should be read as "content of (C-2) component" when applying the invention.

[0270] In the resin composition of the present invention, the total amount of component (C-1) and component (C-2) is 6% by mass or more and 20% by mass or less based on 100% by mass of the resin components in the resin composition. The total amount is preferably 7% by mass or more, more preferably 8% by mass or more, preferably 19% by mass or less, and more preferably 18% by mass or less. When the total amount of component (C-1) and component (C-2) is within the above range, it is possible to obtain a cured product with a small coefficient of linear thermal expansion, which can suppress delamination due to fracture of the cured product, and can also obtain a cured product that exhibits excellent mechanical strength (e.g., puncture strength). Furthermore, when the total amount of component (C-1) and component (C-2) is within the above preferred range, it is possible to obtain a cured product with a small coefficient of linear thermal expansion, which can suppress delamination due to fracture of the cured product, and can also obtain a cured product that can suppress the occurrence of cracks after roughening treatment.

[0271] From the viewpoint of significantly obtaining the desired effects of the present invention, the total amount of component (C-1) and component (C-2) in the resin composition is preferably 5% by mass or more, more preferably 8% by mass or more, even more preferably 10% by mass or more or 12% by mass or more, preferably 40% by mass or less, more preferably 30% by mass or less, and even more preferably 25% by mass or less, based on 100% by mass of the total amount of components (A), (B), and (C) in the resin composition.

[0272] From the viewpoint of significantly obtaining the desired effects of the present invention, the total amount of component (C-1) and component (C-2) in the resin composition is preferably 0.1% by mass or more, more preferably 1% by mass or more, even more preferably 2% by mass or more, preferably 15% by mass or less, more preferably 10% by mass or less, and even more preferably 7% by mass or less, based on 100% by mass of the nonvolatile components in the resin composition.

[0273] The total amount of component (C-1) and component (C-2) relative to 100% by mass of the resin component in the resin composition is M CWhen expressed as [mass %], the mass ratio of components (C-1) and (C-2) to component (A-1) in the resin composition ([total amount of components (C-1) and (C-2)] / [content of component (A-1)]) is M C / M A1 It can be expressed as: Mass ratio M C / M A1 From the viewpoint of significantly obtaining the desired effects of the present invention, the value is preferably 0.1 or higher, more preferably 0.5 or higher, even more preferably 0.8 or higher, preferably 3 or lower, more preferably 2 or lower, and even more preferably 1.6 or lower.

[0274] Furthermore, the mass ratio of components (C-1) and (C-2) to component (A) in the resin composition ([total amount of components (C-1) and (C-2)] / [content of component (A)]) is M C / M A It can be expressed as: Mass ratio M C / M A From the viewpoint of significantly obtaining the desired effects of the present invention, the value is preferably 0.1 or higher, more preferably 0.15 or higher, even more preferably 0.2 or higher, preferably 0.6 or lower, more preferably 0.5 or lower, and even more preferably 0.45 or lower.

[0275] Furthermore, the mass ratio of components (C-1) and (C-2) to component (B) in the resin composition ([total amount of components (C-1) and (C-2)] / [content of component (B)]) is M C / M B It can be expressed as: Mass ratio M C / M A1 From the viewpoint of significantly obtaining the desired effects of the present invention, the value is preferably 0.1 or higher, more preferably 0.2 or higher, even more preferably 0.3 or higher, preferably 1.3 or lower, more preferably 1.2 or lower, and even more preferably 1.1 or lower.

[0276] When the resin composition of the present invention contains (C-1) maleimide resin, from the viewpoint of significantly obtaining the desired effects of the present invention, the content of component (C-1) is preferably 20% by mass or more, more preferably 30% by mass or more or more, even more preferably 31% by mass or more, even more preferably 32% by mass or more or 33% by mass or more, and preferably 100% by mass or less, more preferably 80% by mass or less, even more preferably 70% by mass or less, and even more preferably 60% by mass or less.

[0277] (C-1) The maleimide resin may be an aromatic maleimide resin having maleimide groups directly bonded to an aromatic ring, or an aliphatic maleimide resin not having maleimide groups directly bonded to an aromatic ring. If the (C-1) maleimide resin includes an aliphatic maleimide resin, it is preferable that the aliphatic maleimide resin includes a maleimide resin having a carbon skeleton derived from dimer acid. If the (C-1) maleimide resin includes an aromatic maleimide resin, it is preferable that the aromatic maleimide resin includes a maleimide resin having one or more skeletons selected from a biphenyl skeleton, an indane skeleton, and an aralkyl skeleton.

[0278] The carbon skeleton derived from dimer acid refers to a carbon skeleton obtained by removing the two terminal carboxyl groups (-COOH) of dimer acid, or a carbon skeleton obtained by replacing the two terminal carboxyl groups (-COOH) with methylene groups (-CH2-). Dimer acid is a known compound obtained by dimerizing unsaturated fatty acids (preferably those with 11 to 22 carbon atoms, more preferably those with 14 to 20 carbon atoms, and even more preferably those with 18 carbon atoms), and its industrial production process is largely standardized in the industry. Dimer acid is readily available, particularly those mainly composed of dimer acid with 36 carbon atoms obtained by dimerizing unsaturated fatty acids with 18 carbon atoms, such as oleic acid and linoleic acid, which are inexpensive and readily available. In addition, dimer acid may contain arbitrary amounts of monomeric acids, trimeric acids, and other polymerized fatty acids, depending on the production method, degree of purification, etc. Furthermore, although double bonds remain after the polymerization reaction of unsaturated fatty acids, in this specification, hydrogenated products obtained by further hydrogenation to reduce the degree of unsaturation are also included as dimer acid.

[0279] Maleimide resins having a carbon skeleton derived from dimer acid include maleimide resins represented by the following formula (C1-1).

[0280] [ka]

[0281] (In formula (C1-1), Each of the q1+1 X independently represents a divalent organic group consisting of five or more skeletal atoms selected from carbon atoms, nitrogen atoms (that do not form imides), oxygen atoms, and sulfur atoms, and non-skeletal atoms selected from hydrogen atoms and halogen atoms, and at least one of the q1+1 X represents a divalent hydrocarbon group derived from a dimer acid; Each qY independently represents a tetravalent organic group consisting of five or more skeletal atoms selected from carbon atoms, nitrogen atoms (that do not form imides), oxygen atoms, and sulfur atoms, and non-skeletal atoms selected from hydrogen atoms and halogen atoms; q1 represents a non-negative integer.

[0282] In formula (C1-1), each of the q1+1 X independently represents a divalent organic group consisting of five or more (preferably 5 to 200, more preferably 5 to 100, and even more preferably 5 to 50) skeletal atoms selected from carbon atoms, nitrogen atoms (that do not form imides), oxygen atoms, and sulfur atoms, and non-skeletal atoms selected from hydrogen atoms and halogen atoms. At least one of the q1+1 X represents a divalent hydrocarbon group derived from a dimer acid.

[0283] A divalent hydrocarbon group derived from dimer acid refers to a divalent hydrocarbon group obtained by removing the two terminal carboxyl groups (-COOH) of a dimer acid, or a divalent hydrocarbon group obtained by replacing the two terminal carboxyl groups (-COOH) with methylene groups (-CH2-).

[0284] The divalent organic groups in q1+1 X, other than the divalent hydrocarbon groups derived from the dimer acid, may be divalent organic groups without an aromatic ring, or they may be divalent organic groups having an aromatic ring.

[0285] In formula (C1-1), each q1 Y independently represents a tetravalent organic group consisting of five or more (preferably 5 to 200, more preferably 5 to 100, and even more preferably 5 to 50) skeletal atoms selected from carbon atoms, nitrogen atoms (that do not form imides), oxygen atoms, and sulfur atoms, and non-skeletal atoms selected from hydrogen atoms and halogen atoms. The tetravalent organic group represented by Y may be a tetravalent organic group without an aromatic ring, or a tetravalent organic group having an aromatic ring.

[0286] In one embodiment, the tetravalent organic group represented by Y is preferably a tetravalent group selected from the following formulas (Y1) to (Y5).

[0287] [ka]

[0288] (In formulas (Y1) to (Y5), Ring Y 11 , ring Y 21 , ring Y 22 , ring Y 31 , ring Y 32 , ring Y 33 , ring Y 41 , ring Y 42 , ring Y 43 , ring Y 44 , ring Y 51 , ring Y 52 , ring Y 53 , ring Y 54 and ring Y 55 Each of these independently represents an aromatic ring which may have substituents, or an unaromatic ring which may have substituents; Y 2a , Y 3a , Y 3b , Y 4a , Y 4b , Y 4c , Y 5a , Y 5b , Y 5c and Y 5d These are, independently, single bonds, -C(R C11 ) represents -2-, -O-, -CO-, -S-, -SO-, -SO2-, -CONH-, or -NHCO-; R C11 Each independently represents an alkyl group which may be substituted with a hydrogen atom or a halogen atom, or two R atoms bonded to the same carbon atom. C11 They bond together to form a non-aromatic ring which may have substituents; * indicates a binding site; The two bonding sites on the same ring, represented by *, are bonding sites with two adjacent carbon atoms on that ring.

[0289] In equations (Y1) to (Y5), ring Y 11 , ring Y 21 , ring Y 22 , ring Y 31 , ring Y 32 , ring Y 33 , ring Y 41 , ring Y 42 , ring Y 43 , ring Y 44 , ring Y51 , ring Y 52 , ring Y 53 , ring Y 54 and ring Y 55 Each of these independently represents an optionally substituted aromatic ring or an optionally substituted non-aromatic ring. These cyclic structures are preferably optionally substituted aromatic rings, more preferably optionally substituted benzene rings, and even more preferably alkyl-substituted benzene rings.

[0290] A non-aromatic ring refers to a ring other than an aromatic ring, which has aromaticity throughout the entire ring. A non-aromatic ring may be a non-aromatic carbon ring, which consists only of carbon atoms, or a non-aromatic heteroring, which has heteroatoms such as oxygen, nitrogen, or sulfur atoms in addition to carbon atoms. Non-aromatic carbon rings are preferred. Non-aromatic rings may be saturated or unsaturated rings. Non-aromatic rings are preferably 3 to 21 membered, more preferably 4 to 17 membered, and even more preferably 5 to 14 membered. Suitable examples of non-aromatic rings (non-aromatic carbon rings) include monocyclic non-aromatic saturated carbon rings such as cyclobutane rings, cyclopentane rings, cyclohexane rings, cycloheptane rings, and cyclooctane rings; monocyclic non-aromatic unsaturated carbon rings such as cyclobutene rings, cyclopentene rings, cyclohexene rings, cycloheptene rings, cyclooctene rings, cyclopentadiene rings, and cyclohexadiene rings; bicyclo[2.2.1]heptane rings (norbornane rings), bicyclo[4.4.0]decane rings (decalin rings), bicyclo[5.3.0]decane rings, bicyclo[4.3.0]nonane rings (hydrindane rings), bicyclo[3.2.1]octane rings, bicyclo[5.4.0]undecane rings, bicyclo[3.3.0]octane rings, bicyclo[3.3.1]nonane rings, and tricyclo[5.2.1.0 2,6 ] Decane ring (tetrahydrodicyclopentadiene ring), tricyclo[3.3.1.1 3,7 ] Decane ring (adamantane ring), tricyclo[6.2.1.0 2,7Examples include bicyclic or multicyclic non-aromatic saturated carbocyclic rings such as undecane rings; bicyclic or multicyclic non-aromatic unsaturated carbocyclic rings such as bicyclo[2.2.1]hepta-2-ene rings (norbornene rings), bicyclo[2.2.2]octa-2-ene rings, and bicyclo[4.4.0]deca-2-ene rings; etc. The non-aromatic ring may be a non-aromatic ring in which an aromatic ring is partially fused. Examples of non-aromatic rings in which an aromatic ring is partially fused include indane rings, indene rings, tetralin rings, 1,2-dihydronaphthalene rings, 1,4-dihydronaphthalene rings, fluorene rings, 9,10-dihydroanthracene rings, and 9,10-dihydrophenanthrene rings.

[0291] Ring Y 11 , ring Y 21 , ring Y 22 , ring Y 31 , ring Y 32 , ring Y 33 , ring Y 41 , ring Y 42 , ring Y 43 , ring Y 44 , ring Y 51 , ring Y 52 , ring Y 53 , ring Y 54 and ring Y 55 The substituents that can be present are not particularly limited, but include, for example, halogen atoms, -NO2, -CN, -COH, -OH, -SH, -NH2, -COOH, -R C , -COR C , -OR C , -SR C -SOR C , -SO2R C , -NHR C , -NR C ,-COOR C , -OCOR C -CONH2, -CONHR C ,-CONR C , -NHCOR C Examples of monovalent substituents include (where R C Each of these independently represents a monovalent hydrocarbon group.

[0292] R CThe number of carbon atoms in the monovalent hydrocarbon group represented by is preferably 1 to 50, more preferably 1 to 20. C The monovalent hydrocarbon group represented by may be a monovalent saturated hydrocarbon group or a monovalent unsaturated hydrocarbon group. Also, R C The monovalent hydrocarbon group represented by may or may not have an aromatic structure. C Examples of monovalent hydrocarbon groups represented by include alkyl groups, alkenyl groups, aryl groups, aralkyl groups, and alkylaryl groups.

[0293] The alkyl group may be linear, branched, or cyclic. The number of carbon atoms in the alkyl group is preferably 1 to 14, more preferably 1 to 10, even more preferably 1 to 6, and even more preferably 1 to 3. Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, sec-pentyl, neopentyl, tert-pentyl, hexyl, isohexyl, heptyl, isoheptyl, octyl, isooctyl, tert-octyl, cyclopentyl, cyclohexylmethyl, and the like.

[0294] The alkenyl group may be linear, branched, or cyclic. The number of carbon atoms in the alkenyl group is preferably 2 to 14, more preferably 2 to 10, even more preferably 2 to 6, and even more preferably 2 to 3. Examples of alkenyl groups include vinyl group, propenyl group (allyl group, 1-propenyl group, isopropenyl group), butenyl group (1-butenyl group, clotyl group, methallyl group, isoclotyl group, etc.), pentenyl group (1-pentenyl group, etc.), hexenyl group (1-hexenyl group, etc.), heptenyl group (1-heptenyl group, etc.), octenyl group (1-octenyl group, etc.), cyclopentenyl group (2-cyclopentenyl group, etc.), cyclohexenyl group (3-cyclohexenyl group), and the like.

[0295] The number of carbon atoms in the aryl group is preferably 6 to 14, more preferably 6 to 10. Examples of aryl groups include phenyl, 1-naphthyl, and 2-naphthyl groups.

[0296] The aralkyl group may be an alkyl group substituted with one or more (preferably one) aryl groups. The number of carbon atoms in the aralkyl group is preferably 7 to 15, more preferably 7 to 11. Examples of aralkyl groups include benzyl group, phenethyl group, hydrocinnamyl group, α-methylbenzyl group, α-cumyl group, 1-naphthylmethyl group, and 2-naphthylmethyl group.

[0297] The alkylaryl group may be an aryl group substituted with one or more (preferably one) alkyl groups. The number of carbon atoms in the alkylaryl group is preferably 7 to 15, more preferably 7 to 11. Examples of alkylaryl groups include 4-methylphenyl, 3-methylphenyl, 2-methylphenyl, 4-ethylphenyl, 3-ethylphenyl, 2-ethylphenyl, 4-isopropylphenyl, 3-isopropylphenyl, and 2-isopropylphenyl.

[0298] In equations (Y1) to (Y5), Y 2a , Y 3a , Y 3b , Y 4a , Y 4b , Y 4c , Y 5a , Y 5b , Y 5c and Y 5d These are, independently, single bonds, -C(R C11 )2-, -O-, -CO-, -S-, -SO-, -SO2-, -CONH-, or -NHCO-, preferably a single bond, -C(R C11 It is 2- or -O-.

[0299] R C11 Each of these independently represents an alkyl group which may be substituted with a hydrogen atom or a halogen atom, or two R atoms bonded to the same carbon atom.C11 They bond together to form a non-aromatic ring which may have substituents. The alkyl group is R C It may be the same as the alkyl group in R. C11 Each of these independently preferably represents an alkyl group which may be substituted with a hydrogen atom or a halogen atom; more preferably represents a methyl group which may be substituted with a hydrogen atom or a halogen atom; even more preferably represents a hydrogen atom, a methyl group or a trifluoromethyl group; and even more preferably represents a hydrogen atom or a methyl group.

[0300] R C11 The substituents that can be present are not particularly limited, but include, for example, halogen atoms, -NO2, -CN, -COH, -OH, -SH, -NH2, -COOH, -R C , -COR C , -OR C , -SR C -SOR C , -SO2R C , -NHR C , -NR C ,-COOR C , -OCOR C -CONH2, -CONHR C ,-CONR C , -NHCOR C Examples of monovalent substituents include (R C (As stated above).

[0301] In equation (C1-1), q1 represents an integer greater than or equal to 0, preferably an integer between 0 and 10, and more preferably 0.

[0302] Examples of aromatic maleimide resins include maleimide resins represented by formula (C1-2).

[0303] [ka]

[0304] (In formula (C1-2), RC12 Each of these independently represents an alkyl group which may be substituted with a hydrogen atom or a halogen atom; Ring C 21 and ring C 22 Each of these independently represents an aromatic carbon ring which may have substituents; q 21 represents an integer greater than or equal to 1; q 22 Each of these independently represents a non-negative integer; q 21 Units and q 22 The units may be the same or different for each unit.

[0305] In equation (C1-2), R C12 Each of these independently represents an alkyl group which may be substituted with a hydrogen atom or a halogen atom. The alkyl group is R C It may be the same as the alkyl group in R. C12 Each of these independently preferably represents a hydrogen atom or an alkyl group; more preferably, a hydrogen atom or a methyl group. Among these, q 22 In the embodiment where R is 0, C12 More preferably, q represents a hydrogen atom. 22 In the configuration where is an integer greater than or equal to 1, R C12 It is more preferably a methyl group.

[0306] In equation (C1-2), ring C 21 and ring C 22 Each of these independently represents an aromatic carbon ring, which may have substituents. The aromatic carbon ring is a ring Y. 11 , ring Y 21 , ring Y 22 , ring Y 31 , ring Y 32 , ring Y 33 , ring Y 41 , ring Y 42 , ring Y 43 , ring Y 44 , ring Y 51 , ring Y 52 , ring Y 53 , ring Y 54 and ring Y55 It may be the same as the aromatic carbon ring described in the section on aromatic rings. Also, ring C 21 and ring C 22 In this context, "substituent" refers to, for example, a ring Y. 11 , ring Y 21 , ring Y 22 , ring Y 31 , ring Y 32 , ring Y 33 , ring Y 41 , ring Y 42 , ring Y 43 , ring Y 44 , ring Y 51 , ring Y 52 , ring Y 53 , ring Y 54 and ring Y 55 The substituents may be the same as those that can be present in ring C. 21 and ring C 22 Each of these independently preferably represents a benzene ring which may have substituents; more preferably represents a benzene ring which may be substituted with a group selected from alkyl and aryl groups; and even more preferably represents an (unsubstituted) benzene ring.

[0307] In equation (C1-2), q 21 represents an integer greater than or equal to 1, preferably an integer between 1 and 10. Also, q 22 Each of these independently represents an integer greater than or equal to 0, preferably an integer between 0 and 10, more preferably an integer between 0 and 5, even more preferably 0, 1, or 2, and even more preferably 0 or 1. In the aromatic maleimide resin represented by formula (C1-2), there may be multiple q 22 They may be the same as each other or they may be different, but it is preferable that they be the same as each other.

[0308] Another example of an aromatic maleimide resin is a maleimide resin represented by the following formula (C1-3).

[0309] [ka]

[0310] (In formula (C1-3), R C13 Each of these independently represents an alkyl group which may be substituted with a hydrogen atom or a halogen atom; Ring C 31 , ring C 32 and ring C 33 Each of these independently represents an aromatic carbon ring which may have substituents; q3 represents an integer greater than or equal to 1; q3 The units may be the same or different for each unit.

[0311] In equation (C1-3), R C13 Each of these independently represents an alkyl group which may be substituted with a hydrogen atom or a halogen atom. The alkyl group is R C It may be the same as the alkyl group in R. C13 Each of these is preferably a hydrogen atom or an alkyl group, more preferably a hydrogen atom or a methyl group, and even more preferably a hydrogen atom.

[0312] In equation (C1-3), ring C 31 , ring C 32 and ring C 33 Each of these independently represents an aromatic carbon ring which may have substituents. 31 , ring C 32 and ring C 33 The aromatic carbon ring shown is ring Y. 11 , ring Y 21 , ring Y 22 , ring Y 31 , ring Y 32 , ring Y 33 , ring Y 41 , ring Y 42 , ring Y 43 , ring Y 44 , ring Y 51 , ring Y 52 , ring Y 53 , ring Y 54 and ring Y 55 It may be the same as the aromatic carbon ring described in the section on aromatic rings. Also, ring C 31 , ring C 32 and ring C 33In this context, "substituent" refers to, for example, a ring Y. 11 , ring Y 21 , ring Y 22 , ring Y 31 , ring Y 32 , ring Y 33 , ring Y 41 , ring Y 42 , ring Y 43 , ring Y 44 , ring Y 51 , ring Y 52 , ring Y 53 , ring Y 54 and ring Y 55 The substituents may be the same as those that can be present in ring C. 31 , ring C 32 and ring C 33 Each of these is preferably an optionally substituted benzene ring, more preferably an optionally substituted benzene ring with a group selected from alkyl and aryl groups, and even more preferably an unsubstituted benzene ring.

[0313] In equation (C1-3), q3 represents an integer greater than or equal to 1, and is preferably an integer between 1 and 10.

[0314] Another example of an aromatic maleimide resin is a maleimide resin represented by the following formula (C1-4).

[0315] [ka]

[0316] (In formula (C1-4), R C14 Each of these independently represents an alkyl group; Ring C 41 and ring C 42 Each of these independently represents an aromatic carbon ring which may have substituents; q4 represents an integer greater than or equal to 1; q4 The units may be the same or different for each unit.

[0317] In equation (C1-4), RC14 Each of these independently represents an alkyl group. C14 It is preferable that it be a methyl group.

[0318] In equation (C1-4), ring C 41 Each of these independently represents an aromatic ring which may have substituents. Also, ring C 41 In this context, "substituent" refers to, for example, a ring Y. 11 , ring Y 21 , ring Y 22 , ring Y 31 , ring Y 32 , ring Y 33 , ring Y 41 , ring Y 42 , ring Y 43 , ring Y 44 , ring Y 51 , ring Y 52 , ring Y 53 , ring Y 54 and ring Y 55 The substituents may be the same as those that can be present in ring C. 41 Each of these is preferably an optionally substituted benzene ring, more preferably an optionally substituted benzene ring with an alkyl group, and even more preferably an alkyl group-substituted benzene ring.

[0319] In equation (C1-4), ring C 42 Each of these independently represents an aromatic ring which may have substituents. Also, ring C 42 In this context, "substituent" refers to, for example, a ring Y. 11 , ring Y 21 , ring Y 22 , ring Y 31 , ring Y 32 , ring Y 33 , ring Y 41 , ring Y 42 , ring Y 43 , ring Y 44 , ring Y 51 , ring Y 52 , ring Y 53 , ring Y 54 and ring Y 55 The substituents may be the same as those that can be present in ring C. 42Each of these is preferably an optionally substituted benzene ring, more preferably an optionally substituted alkyl group benzene ring, and even more preferably an unsubstituted benzene ring.

[0320] In equation (C1-4), q4 represents an integer greater than or equal to 1, and is preferably an integer between 1 and 20.

[0321] Another example of an aromatic maleimide resin is the maleimide resin represented by the following formula (C1-5-1).

[0322] [ka]

[0323] (In formula (C1-5-1), R C15 Each of these independently represents an alkylene group; R C16 Each of these independently represents an alkyl group; Z 1 represents a hydrogen atom or a group represented by the following formula (C1-5-2); Z 2 represents a hydrogen atom or a group represented by the following formula (C1-5-3); q 51 This represents an integer greater than or equal to 1, q 51 The units may be the same or different for each unit.

[0324] [ka]

[0325] (In formulas (C1-5-2) and (C1-5-3), R S1 Each of these independently represents a hydrocarbon group having 1 to 18 carbon atoms; s1 represents an integer between 0 and 5; * indicates a binding site; The other symbols are as described above.

[0326] In equations (C1-5-1) and (C1-5-2), R C15 Each of these independently represents an alkylene group. C15 The group is preferably a methylene group, an ethylene group, or an ethylidene group, and more preferably an ethylidene group.

[0327] In equations (C1-5-1) and (C1-5-3), R C16 Each of these independently represents an alkyl group. C16 It is preferable that it be an ethyl group.

[0328] In equation (C1-5-2), R S1 Each of these independently represents a hydrocarbon group with 1 to 18 carbon atoms. S1 It is preferably an alkyl group, and more preferably an ethyl group.

[0329] In equation (C1-5-1), q 51 represents an integer greater than or equal to 1. In formula (C1-5-2), s1 represents an integer between 0 and 5. s1 is preferably 4 or less, more preferably 3 or less, even more preferably 2 or less, and even more preferably 1 or less. In a preferred embodiment, s1 may be 0 or 1.

[0330] Yet another example of an aromatic maleimide resin is a maleimide resin containing the structural unit of the following formula (C1-6-1).

[0331] [ka]

[0332] (in formula (C1-6-1) R C17 Each of these independently represents an alkylene group; L C1 Each of these independently represents a single bond or -O-; R C18 Each of these independently represents an alkyl group; Z 3 This represents the group represented by the following formula (C1-6-2); R S2 and R S3 Each of these independently represents a hydrocarbon group having 1 to 18 carbon atoms; q 61 Each of these independently represents a non-negative integer; q 61 The units may be the same or different for each unit; q 62 Each of these independently represents a non-negative integer; q 62 The units may be the same or different for each unit; q 63 Each of these independently represents a non-negative integer; q 63 The units may be the same or different for each unit; s2 and s3 independently represent 0, 1, or 2, satisfying the relationship 0 ≤ s2 + s3 ≤ 2; Each of s4 independently represents an integer between 0 and 4.

[0333] [ka]

[0334] (In formula (C1-6-2), R S4 Each of these independently represents a hydrocarbon group having 1 to 18 carbon atoms; q 64 Each of these independently represents a non-negative integer; q 64 The units may be the same or different for each unit; Each of s5 independently represents an integer from 0 to 5; * indicates a binding site; The other symbols are as described above.

[0335] In equations (C1-6-1) and (C1-6-2), R C17 Each of these independently represents an alkylene group. C17 The group is preferably a methylene group, an ethylene group, or an ethylidene group, and more preferably a methylene group.

[0336] In equation (C1-6-1), R C18 Each of these independently represents an alkyl group. B62 It is preferable that it be an ethyl group.

[0337] In equation (C1-6-1), R S2 and R S3 Each of these independently represents a hydrocarbon group with 1 to 18 carbon atoms. S2 and R S3 It is preferably an alkyl group, and more preferably a methyl group.

[0338] In equation (C1-6-2), R S4 Each of these independently represents a hydrocarbon group with 1 to 18 carbon atoms. S4 It is preferably an alkyl group, and more preferably a methyl group.

[0339] In equation (C1-6-1), s2 and s3 independently represent 0, 1, or 2, and s2 and s3 satisfy the relationship 0 ≤ s2 + s3 ≤ 2.

[0340] In formula (C1-6-1), each s4 independently represents an integer from 0 to 4. s4 is preferably 3 or less, more preferably 2 or less, and even more preferably 1 or less. In a preferred embodiment, s4 may be 0 or 1.

[0341] In formula (C1-6-2), s5 independently represents an integer from 0 to 5. s5 is preferably 4 or less, more preferably 3 or less, even more preferably 2 or less, and even more preferably 1 or less. In a preferred embodiment, s5 may be 0 or 1.

[0342] The maleimide group equivalent of (C-1) maleimide resin is preferably 50 g / eq. or more, more preferably 100 g / eq. or more, even more preferably 150 g / eq. or more, 200 g / eq. or more, 250 g / eq. or more, or 300 g / eq. or more, with an upper limit preferably 2,000 g / eq. or less, more preferably 1,000 g / eq. or less, even more preferably 800 g / eq. or less, 600 g / eq. or less, 500 g / eq. or less, or 450 g / eq. or less. The maleimide group equivalent is the mass of (C-1) maleimide resin per molar equivalent of maleimide groups.

[0343] (C-1) The molecular weight of the maleimide resin is preferably less than 5,000, more preferably less than 3,000, even more preferably less than 2,000, less than 1,500, less than 1,200, or less than 1,000, and the lower limit is not particularly limited, but may be, for example, 300 or more, 400 or more, 500 or more, etc.

[0344] Commercially available maleimide resins include, for example, dimer amine structure-containing maleimide resins such as "SLK-2600," "SLK-2700-T50," and "SLK-6895-T90" from Shin-Etsu Chemical Co., Ltd.; and dimer amine structure-containing maleimide resins such as "BMI-1500," "BMI-1700," "BMI-3000," "BMI-3000J," "BMI-689," and "BMI-2500" from Designer Molecules Inc. Examples include aromatic maleimide resins such as "BMI-6100" manufactured by Inc.; biphenyl aralkyl maleimide resins such as "MIR-5000-60T", "MIR-3000-70MT", and "MIR-3000-70T" manufactured by Nippon Kayaku Co., Ltd.; "BMI-70" and "BMI-80" manufactured by K.I. Chemicals Co., Ltd.; and "BMI-2300" and "BMI-TMH" manufactured by Yamato Chemical Industries, Ltd. In addition, maleimide resins (indane ring skeleton-containing maleimide compounds) disclosed in the Japan Institute of Invention and Innovation, Technical Report No. 2020-500211 may also be used as maleimide resins.

[0345] Furthermore, the maleimide resin represented by formula (C1-5-1) may be synthesized by known synthesis methods, for example, or a commercially available product may be used. Examples of known synthesis methods include the method described in Synthesis Example 1 of Japanese Patent Application Publication No. 2024-102755.

[0346] Furthermore, as the maleimide resin containing the structural unit represented by formula (C1-6-1), for example, a maleimide resin produced by the following steps (1) and (2) may be used. Step (1): A step of reacting an aromatic amine compound represented by the following formula (c1) with a compound having a benzyl ether skeleton under a solid acid catalyst. Step (2): A step of condensing the intermediate amine compound produced in step (1) with maleic anhydride.

[0347] [ka]

[0348] (In formula (c1), R c1 This represents a hydrocarbon group with 1 to 18 carbon atoms; R c2 and R c3 Each of these independently represents a hydrogen atom or a hydrocarbon group having 1 to 18 carbon atoms; R c4 and R c5 Each of these independently represents either a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.

[0349] (C-2) Polyimide resins can generally be obtained by imidation reactions between diamine compounds and acid anhydrides, or between diisocyanate compounds and acid anhydrides. Specific examples of polyimide resins include, for example, linear polyimides obtained by reacting a bifunctional hydroxyl-terminated polybutadiene, a diisocyanate compound, and a tetrabasic acid anhydride (polyimide described in Japanese Patent Publication No. 2006-37083), and modified polyimides containing a polysiloxane skeleton (polyimides described in Japanese Patent Publication No. 2002-12667 and Japanese Patent Publication No. 2000-319386, etc.). Commercially available polyimide resins may also be used, such as "PIAD200" from Arakawa Chemical Co., Ltd., "SLK-6100" from Shin-Etsu Chemical Co., Ltd., and "Ricacoat SN20" and "Ricacoat PN20" from Shin-Nippon Rika Co., Ltd. Polyimide resin may be used alone or in combination of two or more types.

[0350] In one preferred embodiment, the polyimide resin contains structural units represented by the following formula (C2-1) (hereinafter also referred to as "structural units (C2-1)"). The number of structural units (C2-1) contained in one molecule of polyimide resin is 1 or more, and is not particularly limited, but may be 100 or less, 50 or less, or 30 or less.

[0351] [ka]

[0352] (In formula (C2-1), RC21 This represents a tetravalent group represented by the following formula (C2-2-1); R C22 This represents a divalent group represented by the following formula (C2-2-2).

[0353] [ka]

[0354] (In formula (C2-2-1), Ar C21 Ar C22 Ar C23 and Ar C24 Each of these independently represents an aromatic ring which may have substituents; L C21 , L C22 and L C23 Each of these independently represents a divalent linking group; n C21 represents a non-negative integer; * indicates a binding site.

[0355] [ka]

[0356] (In formula (C2-2-2), Ar C25 Ar C26 Ar C27 and Ar C28 Each of these independently represents an aromatic ring which may have substituents; L C24 , L C25 and L C26 Each of these independently represents a divalent linking group; n C22 represents an integer greater than or equal to 1; * indicates a binding site.

[0357] In equation (C2-2-1), Ar C21 Ar C22 Ar C23 and Ar C24Each of these independently represents an aromatic ring that may or may not have substituents. C21 Ar C22 Ar C23 and Ar C24 The aromatic ring represented by (hereinafter also referred to as "aromatic ring C") is preferably an aromatic ring having 6 to 100 carbon atoms, more preferably 6 to 50 carbon atoms, and even more preferably an aromatic carbon ring having 6 to 100 carbon atoms, and even more preferably 6 to 50 carbon atoms.

[0358] Ar C21 Ar C22 Ar C23 and Ar C24 Examples of aromatic rings represented by Ar include monocyclic aromatic rings such as benzene rings, furan rings, thiophene rings, pyrrole rings, pyrazole rings, oxazole rings, isoxazole rings, thiazole rings, imidazole rings, pyridine rings, pyridazine rings, pyrimidine rings, and pyrazine rings; condensed rings formed by the fusion of two or more monocyclic aromatic rings such as naphthalene rings, anthracene rings, benzofuran rings, isobenzofuran rings, indole rings, isoindole rings, benzothiophene rings, benzimidazole rings, indazole rings, benzoxazole rings, benzoisoxazole rings, benzothiazole rings, quinoline rings, isoquinoline rings, quinoxaline rings, acridine rings, quinazoline rings, sinnoline rings, and phthalazine rings; and condensed rings formed by the fusion of one or more monocyclic aromatic rings with one or more monocyclic non-aromatic rings such as indan rings, fluorene rings, and tetraline rings. C21 Ar C22 Ar C23 and Ar C24 The aromatic rings represented are preferably, independently, aromatic carbon rings having 6 to 14 carbon atoms, which may have substituents, and more preferably, benzene rings.

[0359] In equation (C2-2-1), Ar C21 Ar C22 Ar C23 and Ar C24When represents an aromatic ring having substituents, the number of substituents is not limited. Examples of such substituents (hereinafter also referred to as "substituents S") include, independently of each other, halogen atoms, alkyl groups, cycloalkyl groups, alkoxy groups, cycloalkyloxy groups, aryl groups, aryloxy groups, arylalkyl groups, arylalkoxy groups, monovalent heterocyclic groups, alkylidene groups, amino groups, silyl groups, acyl groups, acyloxy groups, carboxyl groups, sulfo groups, cyano groups, nitro groups, hydroxyl groups, mercapto groups, and oxo groups.

[0360] In equation (C2-2-1), L C21 , L C22 and L C23 Each of these independently represents a divalent linking group. C21 , L C22 and L C23 The divalent linking group represented by is preferably a divalent group consisting of one or more skeletal atoms selected from carbon atoms, oxygen atoms, nitrogen atoms, sulfur atoms, and silicon atoms (for example, 1 to 3000, 1 to 1000, 1 to 100, and 1 to 50 atoms). Examples of divalent linking groups include -SO2-, -CO-, -COO-, -O-, -S-, -O-C6H4-O- (where -C6H4- represents a phenylene group), -O-C6H4-C(CH3)2-C6H4-O-, and -COO-(CH2). r -OCO- (where r represents an integer from 1 to 20), -COO-H2C-HC(-OC(=O)-CH3)-CH2-OCO-, alkylene group, alkenylene group, alkynylene group, arylene group, heteroarylene group, -NR 0 -(Here, R 0 ) represents a hydrogen atom and an alkyl group having 1 to 3 carbon atoms. ) and -C(=O)-NR 0 - are listed.

[0361] L C21 , L C22 and L C23 The number of carbon atoms in the alkylene group is preferably 1 to 10, more preferably 1 to 6, and even more preferably 1 to 5 or 1 to 4. C21 , L C22 and L C23The number of carbon atoms in the alkenylene group is preferably 2 to 10, more preferably 2 to 6, and even more preferably 2 to 5. C21 , L C22 and L C23 The number of carbon atoms in the arylene group is preferably 6 to 20, more preferably 6 to 10. C21 , L C22 and L C23 The number of carbon atoms in the heteroarylene group is preferably 2 to 20, more preferably 3 to 10, 4 to 10, or 5 to 10.

[0362] L C21 , L C22 and L C23 The divalent linking group represented by preferably does not contain an aromatic ring. In one embodiment, L C21 The divalent linking group and L C23 The divalent linking groups represented by are the same as L C21 The divalent linking group and L C22 The divalent linking groups represented by are different from each other. In one preferred embodiment, L C21 and L C23 is -O-, L C22 is an alkylene group which may have substituents. In a more preferred embodiment, L C21 and L C23 is -O-, L C22 This is a dimethylmethylene group.

[0363] In equation (C2-2-1), n C21 n represents an integer greater than or equal to 0. In a preferred embodiment, n C21 n represents an integer greater than or equal to 1. C21 The upper limit of the integer represented by is not particularly restricted, but it could be, for example, 50, 40, 30, or 20.

[0364] In the tetravalent group represented by formula (C2-2-1), L C21 and L C23 is -O- and L C22 It is preferable that is an alkylene group which may have substituents. Also, Ar C21 ArC22 Ar C23 and Ar C24 However, each is independently an aromatic carbon ring having 6 to 14 carbon atoms, which may have substituents, L C21 and L C23 is -O- and L C22 It is more preferable that is an alkylene group which may have substituents. Also, Ar C21 Ar C22 Ar C23 and Ar C24 However, each is independently an aromatic carbon ring having 6 to 14 carbon atoms, which may have substituents, L C21 and L C23 is -O- and L C22 It is even more preferable that the group is a dimethylmethylene group.

[0365] In equation (C2-2-2), Ar C25 Ar C26 Ar C27 and Ar C28 Each of these independently represents an aromatic ring that may or may not have substituents. C25 Ar C26 Ar C27 and Ar C28 Examples of the aromatic ring represented by and the substituents that the aromatic ring may have are the same as those described above for the aromatic ring C and substituent S. Therefore, in one preferred embodiment, Ar C25 Ar C26 Ar C27 and Ar C28 Each of these is independently an aromatic carbon ring having 6 to 14 carbon atoms, which may have substituents.

[0366] In equation (C2-2-2), L C24 , L C25 and L C26 Each of these independently represents a divalent linking group. C24 , L C25 and L C26 An example of a divalent linking group represented by is L C21 , L C22 and L C23This is similar to the divalent linking group represented by . Therefore, in a preferred embodiment, L C24 and L C26 is -O-, L C25 is an alkylene group which may have substituents, and in a more preferred embodiment, L C24 and L C26 is -O-, L C25 This is a dimethylmethylene group.

[0367] In equation (C2-2-2), n C22 n represents an integer greater than or equal to 1. In one preferred embodiment, n C22 n represents an integer greater than or equal to 2. C22 The upper limit of the integer represented by is not particularly restricted, but it could be, for example, 60, 50, 40, or 30.

[0368] In the divalent group represented by formula (C2-2-2), L C24 and L C26 is -O- and L C25 It is preferable that is an alkylene group which may have substituents. Also, Ar C25 Ar C26 Ar C27 and Ar C28 However, each is independently an aromatic carbon ring having 6 to 14 carbon atoms, which may have substituents, L C24 and L C26 is -O- and L C25 It is more preferable that is an alkylene group which may have substituents. Also, Ar C25 Ar C26 Ar C27 and Ar C28 However, each is independently an aromatic carbon ring having 6 to 14 carbon atoms, which may have substituents, L C24 and L C26 is -O- and L C25 It is even more preferable that the group is a dimethylmethylene group.

[0369] In the tetravalent group represented by formula (C2-2-1) and the divalent group represented by formula (C2-2-2), Ar C21 ArC22 Ar C23 and Ar C24 However, each is independently an aromatic carbon ring having 6 to 14 carbon atoms, which may have substituents, and Ar C25 Ar C26 Ar C27 and Ar C28 However, each is preferably an aromatic carbon ring having 6 to 14 carbon atoms, which may have substituents. C21 and L C23 is -O-, L C22 L is an alkylene group which may have substituents. C24 and L C26 is -O- and L C25 It is preferable that the alkylene group may have substituents.

[0370] The above structural unit (C2-1) can be obtained, for example, by known methods for producing polyimide resins, typically by polymerizing a monomer composition containing a tetracarboxylic dianhydride and a diamine compound to imidize it, or by polymerizing a monomer composition containing a tetracarboxylic dianhydride and a diisocyanate compound to imidize it. It is acceptable for the polyimide resin to partially contain polyamic acid structures that may be formed during the imidization process.

[0371] The structural unit (C2-1) may be obtained, for example, by reacting 2,2-bis[4-(3,4-dicarboxyphenoxy)phenyl]propane dianhydride (a compound represented by the following formula (C2-3-1); hereinafter also referred to as "BPADA") with 4,4'-[1,4-phenylenebis[(1-methylethylidene)-4,1-phenyleneoxy]]bisbenzeneamine (a compound represented by the following formula (C2-3-2); hereinafter also referred to as "BPPAN"). That is, in one embodiment, the R in the structural unit (C2-1) C21 It is a skeleton derived from BPADA, and R C22 This is a skeleton derived from BPPAN.

[0372] [ka]

[0373] Furthermore, the polyimide resin may also contain structural units represented by the following formula (C2-4) (hereinafter also referred to as "structural units (C2-4)"). Therefore, in one embodiment, the polyimide resin further contains structural units represented by the following formula (C2-4). The number of structural units (C2-4) contained in one molecule of polyimide resin is 0 or more and is not particularly limited, but can be 100 or less, 50 or less, or 30 or less.

[0374] [ka]

[0375] (In formula (C2-4), R C23 This represents a tetravalent aliphatic group which may have a substituent or a tetravalent aromatic group which may have a substituent; R C24 R represents a divalent aliphatic group which may have substituents or a divalent aromatic group which may have substituents. However, R C23 R C21 In the same case, R C24 is R C22 Unlike R C24 R C22 In the same case, R C23 is R C21 (This is different.)

[0376] In equation (C2-4), R C23 This represents a tetravalent aliphatic group that may have substituents or a tetravalent aromatic group that may have substituents.

[0377] R C23 The tetravalent aliphatic group represented by is a tetravalent group comprising at least carbon atoms, and preferably consisting of one or more skeletal atoms selected from carbon atoms, oxygen atoms, nitrogen atoms, sulfur atoms, and silicon atoms (e.g., 1 to 3000, 1 to 1000, 1 to 100, 1 to 50). C23The tetravalent aliphatic group represented by is more preferably a tetravalent aliphatic group having 1 to 100 carbon atoms, and even more preferably 1 to 50 carbon atoms. In formula (C2-4), R C23 When represents a tetravalent aliphatic group having a substituent, the examples of the substituent are the same as the examples of substituent S.

[0378] R C23 The tetravalent aromatic group represented by is preferably a tetravalent aromatic group having 6 to 100 carbon atoms, more preferably 6 to 50 carbon atoms. The aromatic group contains at least an aromatic ring. An example of an aromatic ring contained in an aromatic group is Ar in formula (C2-2-1). C21 Ar C22 Ar C23 and Ar C24 This is the same as the example of an aromatic ring represented by . In equation (C2-4), R C23 When represents a tetravalent aromatic group having a substituent, the examples of the substituent are the same as the examples of substituent S.

[0379] R C23 Examples of tetravalent aromatic groups represented by include groups obtained by removing two acid anhydride groups from a tetracarboxylic dianhydride having an aromatic group that may have substituents. Specific examples of tetracarboxylic dianhydrides having an aromatic group that may have substituents include BPADA, pyromellitic dianhydride, 3,3',4,4'-biphenyltetracarboxylic dianhydride, 4,4'-oxydiphthalic anhydride, 3,3',4,4'-benzophenonetetracarboxylic dianhydride, and 3,3',4,4'-diphenylsulfonetetracarboxylic dianhydride.

[0380] In equation (C2-4), R C24 This represents a divalent aliphatic group or a divalent aromatic group that may have substituents.

[0381] R C24The divalent aliphatic group represented by is a divalent group comprising at least carbon atoms, and preferably consisting of one or more skeletal atoms selected from carbon atoms, oxygen atoms, nitrogen atoms, sulfur atoms, and silicon atoms (e.g., 1 to 3000, 1 to 1000, 1 to 100, 1 to 50). In formula (C2-4), R C24 The divalent aliphatic group represented by is more preferably a divalent aliphatic group having 1 to 100 carbon atoms, and even more preferably 1 to 50 carbon atoms.

[0382] In equation (C2-4), R C24 When R represents a divalent aliphatic group having a substituent, the examples of the substituent are the same as the examples of substituent S, for example, alkyl groups having 1 to 6 carbon atoms. Therefore, in one embodiment, R C24 is a divalent aliphatic group which may have substituents, and one of the substituents is an alkyl group having 1 to 6 carbon atoms. In one embodiment, R C24 However, it is a divalent aliphatic group which may have substituents, and is a divalent group obtained by removing two amino groups from isophoronediamine.

[0383] R C24 When represents a divalent aliphatic group which may have substituents, it may be a group obtained by removing two amino groups from a diamine compound having a linear aliphatic group which may have substituents, selected from 1,2-diaminoethane, 1,3-diaminopropane, 1,4-diaminobutane, 1,5-diaminopentane, 1,6-hexanediamine, 1,7-heptanediamine, 1,8-octanediamine, 1,9-nonanediamine, 1,10-decanediamine, 1,11-undecanediamine, and 1,12-dodecanediamine.

[0384] R C24When represents a divalent aliphatic group which may have substituents, it may be a group obtained by removing two amino groups from a diamine compound having a branched aliphatic group which may have substituents, selected from 1,2-diaminopropane, 1,2-diamino-2-methylpropane, 1,3-diamino-2-methylpropane, 1,3-diamino-2,2-dimethylpropane, 1,3-diaminopentane, and 1,5-diamino-2-methylpentane.

[0385] R C24 When represents a divalent aliphatic group which may have substituents, 5-amino-1,3,3-trimethylcyclohexanemethylamine (isophorone diamine), 1,4-diaminocyclohexane, 1,3-diaminocyclohexane, 1,4-cyclohexanebis(methylamine), 1,3-cyclohexanebis(methylamine), 4,4'-diaminodicyclohexylmethane, bis(4-amino-3-methylcyclohexyl)methane, 3(4),8(9)-bis(aminomethyl)tricyclo[5.2.1.0 2,6 The group may be a diamine compound having an aliphatic group which may have substituents, selected from decane, 2,5(6)-bis(aminomethyl)bicyclo[2.2.1]heptane, 1,3-diaminoadamantane, 3,3'-diamino-1,1'-biadamantyl, and 1,6-diaminoadamantane, from which two amino groups have been removed. These diamine compounds are characterized in that their aliphatic group contains an alicyclic carbocyclic ring.

[0386] R C24 The divalent aromatic group represented by is preferably a divalent aromatic group having 6 to 100 carbon atoms, more preferably 6 to 50 carbon atoms. The aromatic group contains at least an aromatic ring. Examples of aromatic rings included in the aromatic group are the same as examples of aromatic ring C. In formula (C2-4), R C24 When represents a divalent aromatic group having a substituent, the examples of the substituent are the same as the examples of substituent S.

[0387] R C24However, when representing a divalent aromatic group which may have substituents, it may be a group obtained by removing two amino groups from a diamine compound having an aromatic group which may have substituents, selected from 4,4'-diaminodiphenyl ether, 1,4-phenylenediamine, and 2,2-bis[4-(4-aminophenoxy)phenyl]propane.

[0388] However, R C23 R C21 In the same case, R C24 is R C22 Unlike R C24 R C22 In the same case, R C23 is R C21 It is different. In one embodiment, R C23 is R C21 It is the same as this.

[0389] The structural unit (C2-4) described above can be obtained, for example, by a known method for producing polyimide resins. The structural unit (C2-4) can be obtained, for example, by reacting BPADA with isophorone diamine. That is, the R in such structural unit (C2-4) C23 In one embodiment, this is a skeleton derived from BPADA, and R C24 This is a skeleton derived from isophorone diamine. C23 R C21 If it is the same as R C23 and R C21 In one embodiment, this is a skeleton derived from BPADA.

[0390] The content of structural units (C2-1) in the polyimide resin is preferably 5% by mass or more, more preferably 10% by mass or more, and even more preferably 20% by mass or more, 30% by mass or more, or 40% by mass or more. The upper limit of this content can be, for example, 98% by mass or less, 95% by mass or less, 90% by mass or less, or 85% by mass or less. Here, the content of structural units (C2-1) (mass percentage) can be calculated from the proportion of the amount (parts by mass) of each material used in the synthesis of the polyimide resin. Alternatively, the molecular weight of the polyimide resin and the formula weight of structural units (C2-1) may be specified, and the content may be calculated as the ratio of the formula weight of structural units (C2-1) to the molecular weight. When the polyimide resin is a polymer, it is preferable that the content of structural units (C2-1) estimated from the degree of polymerization falls within the above range.

[0391] The content of structural unit (C2-4) in the polyimide resin may be 0% by mass (i.e., no structural unit (C2-4)), and there is no upper limit as long as it does not hinder the effects of the present invention. If the polyimide resin further contains structural unit (C2-4), the content of structural unit (C2-4) in the polyimide resin may be, for example, 1% by mass or more, 5% by mass or more, 10% by mass or more, 20% by mass or more, or 30% by mass or more, 95% by mass or less, 90% by mass or less, 80% by mass or less, 70% by mass or less, or 60% by mass or less. Here, the content of structural unit (C2-4) is calculated in the same way as the content of structural unit (C2-1).

[0392] The terminal structure of the polyimide resin is not particularly limited. For example, the terminal structure of the polyimide resin may be an acid anhydride group, a carboxyl group, or an amino group derived from its raw material compound (e.g., an acid such as BPADA, or an amine compound such as BPPAN).

[0393] In one preferred embodiment, the polyimide resin contains end groups represented by the following formula (C2-5). In such an embodiment, when the polyimide resin contains two or more end groups represented by the formula (C2-5), these two or more end groups may be the same or different, but it is preferable that they be the same.

[0394] [ka]

[0395] (In formula (C2-5), (i)R C25 and R C26 They combine to form a non-aromatic ring containing an ethylenically unsaturated bond, which may be substituted with a monovalent hydrocarbon group, or (ii)R C25 and R C26 Each of these independently consists of a hydrogen atom, a monovalent hydrocarbon group, or =C(R C27 ) represents 2, and R C25 and R C26 At least one of them is a monovalent hydrocarbon group containing an ethylenically unsaturated bond, or =C(R C27 )2; R C27 Each of these independently represents either a hydrogen atom or an alkyl group having 1 to 10 carbon atoms; * indicates a binding site.

[0396] In the first embodiment (i) of the terminal group represented by formula (C2-5), R C25 and R C26 These combine to form a non-aromatic ring containing an ethylenically unsaturated bond, which may be substituted with a monovalent hydrocarbon group. The ethylenically unsaturated bond and the non-aromatic ring are as described above. C25 and R C26 The non-aromatic ring formed may be a non-aromatic carbon ring or a non-aromatic heterocycle. Non-aromatic carbon rings and non-aromatic heterocycles are as described above.

[0397] Examples of monovalent hydrocarbon groups as substituents include alkyl groups, alkenyl groups, aryl groups, aralkyl groups, alkylaryl groups, alkylaralkyl groups, alkenylaryl groups, and alkenylaralkyl groups. Alkyl groups, alkenyl groups, aryl groups, aralkyl groups, and alkylaryl groups are as described above.

[0398] An alkylaralkyl group refers to an aralkyl group in which an aromatic carbon atom is substituted with one or more (preferably one) alkyl groups. Unless otherwise specified, alkylaralkyl groups with 8 to 16 carbon atoms are preferred, and alkylaralkyl groups with 8 to 12 carbon atoms are more preferred. Examples of alkylaralkyl groups include 4-methylbenzyl group, 3-methylbenzyl group, 2-methylbenzyl group, 4-ethylbenzyl group, 3-ethylbenzyl group, 2-ethylbenzyl group, 4-isopropylbenzyl group, 3-isopropylbenzyl group, and 2-isopropylbenzyl group.

[0399] An alkenylaryl group refers to an aryl group substituted with one or more (preferably one) alkenyl groups. Unless otherwise specified, alkenylaryl groups having 8 to 15 carbon atoms are preferred, and alkenylaryl groups having 8 to 11 carbon atoms are more preferred. Examples of alkenylaryl groups include 4-vinylphenyl, 3-vinylphenyl, 2-vinylphenyl, 4-isopropenylphenyl, 3-isopropenylphenyl, and 2-isopropenylphenyl.

[0400] An alkenyl aralkyl group refers to an aralkyl group in which an aromatic carbon atom is substituted with one or more (preferably one) alkenyl groups. Unless otherwise specified, alkenyl aralkyl groups with 9 to 16 carbon atoms are preferred, and alkyl aralkyl groups with 9 to 12 carbon atoms are more preferred. Examples of alkenyl aralkyl groups include 4-vinylbenzyl, 3-vinylbenzyl, 2-vinylbenzyl, 4-isopropenylbenzyl, 3-isopropenylbenzyl, and 2-isopropenylbenzyl groups.

[0401] Specific examples of non-aromatic carbocyclic rings containing ethylenically unsaturated bonds and which may be substituted with monovalent hydrocarbon groups include monocyclic non-aromatic carbocyclic rings such as cyclobutene rings, cyclopentene rings, cyclohexene rings, cycloheptene rings, and cyclooctene rings; bicyclic non-aromatic carbocyclic rings such as bicyclo[2.2.1]hepta-2-ene rings (norbornene rings), bicyclo[2.2.2]octa-2-ene rings, and bicyclo[4.4.0]deca-2-ene rings; and tricyclo[5.2.1.0 2,6 Examples include non-aromatic tricyclic carbon rings such as deca-3-ene rings.

[0402] Specific examples of non-aromatic heterocycles containing ethylenically unsaturated bonds and which may be substituted with monovalent hydrocarbon groups include bicyclic non-aromatic heterocycles such as the 7-oxabicyclo[2.2.1]hepta-2-ene ring.

[0403] In the first embodiment (i) of the terminal group represented by formula (C2-5), R C25 and R C26 However, it is preferable to form a 5-18 member non-aromatic ring containing an ethylenically unsaturated bond, which may be substituted with a group selected from alkyl groups, alkenyl groups, aryl groups, aralkyl groups, alkylaryl groups, alkylaralkyl groups, alkenylaryl groups, and alkenylaralkyl groups; R C25 and R C26 However, it is more preferable to form a 5-14 member non-aromatic ring containing an ethylenically unsaturated bond, which may be substituted with an alkyl group; R C25 and R C26 However, it is even more preferable to form a cyclohexene ring which may be substituted with an alkyl group, a bicyclo[2.2.1]hepta-2-ene ring which may be substituted with an alkyl group, a bicyclo[2.2.2]octa-2-ene ring which may be substituted with an alkyl group, or a 7-oxabicyclo[2.2.1]hepta-2-ene ring which may be substituted with an alkyl group.

[0404] In the second embodiment (ii) of the terminal group represented by formula (C2-5), R C25 and R C26each independently represents a hydrogen atom or a monovalent hydrocarbon group, and R C25 and R C26 at least one of which is a monovalent hydrocarbon group containing an ethylenically unsaturated bond. The ethylenically unsaturated bond is as described above. Also, the monovalent hydrocarbon groups represented by R C25 and R C26 are the same as the "monovalent hydrocarbon group as a substituent" described above.

[0405] In the second embodiment (ii) of the end group represented by the formula (C2-5), R C25 and R C26 each independently represents a hydrogen atom, an alkyl group, an alkenyl group, an aryl group, an aralkyl group, an alkylaryl group, an alkylaralkyl group, an alkenylaryl group, or an alkenylaralkyl group, and at least one of R C25 and R C26 is preferably an alkenyl group, an alkenylaryl group, or an alkenylaralkyl group; R C25 and R C26 each independently represents a hydrogen atom or an alkenyl group, and it is more preferable that at least one of R C25 and R C26 is an alkenyl group; it is even more preferable that R C25 is an alkenyl group and R C26 is a hydrogen atom. The alkyl group, alkenyl group, aryl group, aralkyl group, and alkylaryl group are as described above.

[0406] The end group represented by the formula (C2-5) is preferably any of the end groups represented by the following formulas (C2-6-1) to (C2-6-8), and more preferably any of the end groups represented by the formula (C2-6-1), the formula (C2-6-2), the formula (C2-6-6), and the formula (C2-6-8).

[0407]

Chemical formula

[0408] (In formulas (C2-6-1) to (C2-6-8), R C27 Each of these independently represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms; X c represents -O-, -CH2-, or -CH2CH2-; * indicates a binding site.

[0409] The terminal group represented by formula (C2-5) is more preferably one of the terminal groups represented by the following formulas (C2-7-1) to (C2-7-12).

[0410] [ka]

[0411] The weight-average molecular weight (Mw) of the polyimide resin is preferably 1,000 or more, preferably 200,000 or less, more preferably 150,000 or less or 100,000 or less, even more preferably 80,000 or less or 60,000 or less, and even more preferably 40,000 or less or 30,000 or less. The weight-average molecular weight of the polyimide resin is the weight-average molecular weight in terms of polystyrene, measured by gel permeation chromatography (GPC).

[0412] From the viewpoint of significantly obtaining the desired effects of the present invention, in the resin composition of the present invention, (C) component contains (C-1) maleimide resin, (A-1) The epoxy equivalent of the high viscosity epoxy resin is 150 g / eq. or more and 5,000 g / eq. or less. (B) The active ester group equivalent of the active ester resin containing radical polymerizable groups is 120 g / eq. or more and 1,000 g / eq. or less. (C-1) The maleimide group equivalent of the maleimide resin is preferably 50 g / eq. to 2,000 g / eq.

[0413] <(D) Other thermosetting resins> The resin composition of the present invention may contain (D) other thermosetting resins as an optional component. The (D) other thermosetting resins do not include those corresponding to components (A) to (C) described above. The (D) other thermosetting resins may be used individually or in combination of two or more types.

[0414] (D) Examples of other thermosetting resins include phenol resins, activated ester resins that do not contain radical polymerizable groups, carbodiimide resins, cyanate ester resins, benzoxazine resins, acid anhydride resins, amine resins, and thiol resins. When the resin composition contains (D) other thermosetting resins, (D) other thermosetting resins preferably contain at least one thermosetting resin selected from the group consisting of phenol resins, activated ester resins that do not contain radical polymerizable groups, and carbodiimide resins, more preferably contain at least one of phenol resins and activated ester resins that do not contain radical polymerizable groups, and even more preferably contain phenol resins.

[0415] As the phenolic resin, a resin having one or more, preferably two or more, hydroxyl groups (phenolic hydroxyl groups) bonded to aromatic rings such as benzene rings and naphthalene rings per molecule can be used. When combined with an epoxy resin, the phenolic resin can react with the epoxy resin to cure the resin composition, and is therefore sometimes called a "phenolic curing agent." From the viewpoint of heat resistance and water resistance, a phenolic resin having a novolac structure is preferred. Furthermore, from the viewpoint of adhesion, a nitrogen-containing phenolic resin is preferred, and a triazine skeleton-containing phenolic resin is more preferred. Among these, a triazine skeleton-containing phenol novolac resin is preferred from the viewpoint of highly satisfying heat resistance, water resistance, and adhesion. The phenolic resin may be used alone or in combination of two or more types.

[0416] Specific examples of phenolic resins include "MEH-7700", "MEH-7810", "MEH-7851", and "MEH-8000H" from Meiwa Kasei Co., Ltd.; "NHN", "CBN", and "GPH" from Nippon Kayaku Co., Ltd.; and "SN-170", "SN-180", "SN-190", "SN-475", "SN-485", "SN-495", "SN-495V", and "SN-3" from Nippon Steel Chemical & Material Co., Ltd. Examples include "75", "SN-395", "TD-2090", "TD-2090-60M", "LA-7052", "LA-7054", "LA-1356", "LA-3018", "LA-3018-50P", "LA-1356", "TD2090", "TD-2090-60M", and "GDP-6115L", "GDP-6115H", and "ELPC75" from Gun-ei Chemical Co., Ltd.

[0417] As active ester resins that do not contain radical polymerizable groups, compounds having two or more highly reactive ester groups in one molecule, such as phenol esters, thiophenol esters, N-hydroxyamine esters, and esters of heterocyclic hydroxy compounds, are generally preferred. Active ester resins can react with epoxy resins to cure the resin composition when combined with epoxy resins, and are therefore sometimes called "active ester curing agents." Active ester resins that do not contain radical polymerizable groups are preferably obtained by the condensation reaction of carboxylic acid compounds and / or thiocarboxylic acid compounds with hydroxy compounds and / or thiol compounds. Furthermore, active ester resins obtained from carboxylic acid compounds and hydroxy compounds are preferred, and active ester resins obtained from carboxylic acid compounds and phenol compounds and / or naphthol compounds are more preferred. Examples of carboxylic acid compounds include benzoic acid, acetic acid, succinic acid, maleic acid, itaconic acid, phthalic acid, isophthalic acid, terephthalic acid, and pyromellitic acid. Examples of phenol compounds or naphthol compounds include hydroquinone, resorcinol, bisphenol A, bisphenol F, bisphenol S, phenolphthalein, methylated bisphenol A, methylated bisphenol F, methylated bisphenol S, phenol, o-cresol, m-cresol, p-cresol, catechol, α-naphthol, β-naphthol, 1,5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 2,6-dihydroxynaphthalene, dihydroxybenzophenone, trihydroxybenzophenone, tetrahydroxybenzophenone, phloroglucin, benzenetriol, dicyclopentadiene-type diphenol compounds, and phenol novolac. Here, "dicyclopentadiene-type diphenol compound" refers to a diphenol compound obtained by condensing two molecules of phenol with one molecule of dicyclopentadiene. Active ester resins that do not contain radical polymerizable groups may be used individually or in combination of two or more types.

[0418] Specifically, as the active ester resin not containing a radically polymerizable group, it is preferably at least one selected from a dicyclopentadiene-type active ester resin, a naphthalene-type active ester resin containing a naphthalene structure, an active ester resin containing an acetylated product of phenol novolak, and an active ester resin containing a benzoylated product of phenol novolak. Among them, it is more preferably at least one selected from a dicyclopentadiene-type active ester resin and a naphthalene-type active ester resin. As the dicyclopentadiene-type active ester resin, an active ester resin containing a dicyclopentadiene-type diphenol structure is preferable.

[0419] From the viewpoint of more significantly obtaining the desired effects of the present invention, the component (D) preferably contains a monovalent group represented by the following formula (D’). There is no particular limitation on the position where the component (D) contains a monovalent group represented by the following formula (D’). In a preferred embodiment, the component (D) may contain a monovalent group represented by the following formula (D’) as a substituent.

[0420]

Chemical formula

[0421] (In the formula (D’), Ar D1 represents a divalent aromatic group which may have a substituent; Ar D2 represents a monovalent aromatic group which may have a substituent; Ar D1 and Ar D2 do not contain a radically polymerizable group in any of them; * represents a bonding site.)

[0422] In the formula (D’), Ar D1 represents a divalent aromatic group which may have a substituent. Also, in the formula (D’), Ar D2 represents a monovalent aromatic group which may have a substituent. Here, Ar D1 and Ar D2The aromatic rings that make up the compound may be aromatic carbocyclic rings or aromatic heterocyclic rings. That is, Ar D1 This may be an arylene group which may have substituents, or a heteroarylene group which may have substituents. D2 This may be an aryl group which may have substituents, or a heteroaryl group which may have substituents. In particular, Ar D1 It is preferable that it is an arylene group which may have substituents. Also, Ar D2 It is preferable that is an aryl group which may have substituents. Furthermore, Ar D1 is an arylene group which may have substituents, and Ar D2 It is more preferable that the group is an aryl group which may have substituents. D1 and Ar D2 The substituents that may be present are the same as those that may be present on the aromatic ester skeleton described above.

[0423] As mentioned earlier, Ar D1 and Ar D2 Each of these may have a substituent, but Ar D1 and Ar D2 None of these contain radical polymerizable groups. D1 and Ar D2 The substituents that each of them may have include, for example, halogen atoms, hydroxyl groups, and -OC groups. 1-6 Alkyl, -N(C 1-10 Alkyl groups)2, alkyl groups with 1 to 20 carbon atoms, aryl groups with 6 to 10 carbon atoms, aralkyl groups with 7 to 10 carbon atoms, amino groups, cyano groups, -C(O)OC 1-10 Examples include alkyl groups, carboxyl groups, formyl groups, and nitro groups.

[0424] In cured resin compositions, from the viewpoint of further suppressing the occurrence of cracks after roughening treatment, it is preferable that the active ester resin, which does not contain radical polymerizable groups, contains an active ester compound represented by the following formula (D-1).

[0425] [ka]

[0426] (In formula (D-1), Ar 51 Each of these independently represents a monovalent aromatic group which may have substituents; Ar 52 Each of these independently represents a divalent aromatic group which may have substituents; Ar 53 Each of these independently represents a divalent aromatic group containing a fused ring structure, which may have substituents; R 51 Each of these independently represents a divalent hydrocarbon group which may have substituents; Ar 51 Ar 52 Ar 53 and R 51 None of these contain radical polymerizable groups; n 51 (This represents an integer greater than or equal to 0.)

[0427] In equation (D-1), Ar 51 Each of these independently represents a monovalent aromatic group which may have substituents. 51 The number of carbon atoms in the monovalent aromatic group represented by is preferably 6 to 30, more preferably 6 to 20, and even more preferably 6 to 10. This number of carbon atoms does not include the number of carbon atoms in substituents. 51 Examples of monovalent aromatic groups represented by include, for example, aryl groups and heteroaryl groups. 51 The monovalent aromatic group represented by is preferably an aryl group, more preferably a naphthyl group, even more preferably a 1-naphthyl group or a 2-naphthyl group, and even more preferably a 1-naphthyl group.

[0428] In equation (D-1), Ar 52 Each of these independently represents a divalent aromatic group which may have substituents. 52The number of carbon atoms in the divalent aromatic group represented by is preferably 6 to 24, more preferably 6 to 18, and even more preferably 6 to 14. 52 Examples of divalent aromatic groups represented by include, for example, arylene groups and heteroarylene groups. 52 The divalent aromatic groups represented by are, independently, preferably arylene groups, more preferably phenylene groups, and even more preferably 1,3-phenylene groups.

[0429] In equation (D-1), Ar 53 Each of these independently represents a divalent aromatic group containing a fused ring structure. Also, Ar 53 It may have substituents. 53 The number of carbon atoms in the divalent aromatic group containing the fused ring structure represented by is preferably 6 or more, more preferably 7 or more, even more preferably 8 or more, preferably 24 or less, more preferably 18 or less, and even more preferably 14 or less. 53 Examples of divalent aromatic groups containing a fused ring structure, as represented by , include arylene groups containing a fused ring structure and heteroarylene groups containing a fused ring structure.

[0430] Examples of arylene groups containing a fused ring structure include naphthylene groups such as 1,2-naphthylene, 1,3-naphthylene, 1,4-naphthylene, 1,5-naphthylene, 1,6-naphthylene, 1,7-naphthylene, and 1,8-naphthylene; anthracenylene groups; phenanthrendyl groups; and the like.

[0431] Examples of heteroarylene groups containing a fused ring structure include carbazole diyl groups, quinoline diyl groups, and isoquinoline diyl groups.

[0432] Among them, Ar 53 The divalent aromatic groups containing a fused ring structure represented by are preferably arylene groups containing a fused ring structure, and more preferably naphthylene groups.

[0433] In equation (D-1), R51 Each of these independently represents a divalent hydrocarbon group which may have substituents. 51 Examples of divalent hydrocarbon groups represented by include divalent aromatic hydrocarbon groups, divalent saturated aliphatic hydrocarbon groups, or divalent groups consisting of a combination of a divalent aromatic hydrocarbon group and a divalent saturated aliphatic hydrocarbon group.

[0434] R 51 Examples of divalent aromatic hydrocarbon groups that can be represented include the arylene group. Also, R 51 Examples of divalent saturated aliphatic hydrocarbon groups that can be represented include alkylene groups and cycloalkylene groups. 51 Specific examples of alkylene groups and cycloalkylene groups that can be represented include those described above in the sections on alkylene groups and cycloalkylene groups that component (B-1) may have.

[0435] R 51 Examples of divalent groups that can be represented by a combination of a divalent aromatic hydrocarbon group and a divalent saturated aliphatic hydrocarbon group include alkylene-arylene groups, alkylene-arylene-alkylene groups, arylene-alkylene-arylene groups, and so on.

[0436] Among them, R 51 Each of these groups is preferably a divalent group consisting of a combination of a divalent aromatic hydrocarbon group and a divalent saturated aliphatic hydrocarbon group, more preferably an alkylene-arylene-alkylene group, even more preferably a methylene-phenylene-methylene group, and even more preferably a methylene-1,4-phenylene-methylene group.

[0437] As mentioned earlier, Ar 51 Ar 52 Ar 53 and R 51 Each of these may have a substituent, but Ar 51 Ar 52 Ar 53 and R 51 None of these contain radical polymerizable groups. 51, Ar 52 , Ar 53 and R 51 Examples of the substituents that Ar, Ar, and R may each have include, for example, a halogen atom, a hydroxyl group, -O-C 1-6 alkyl group, -N(C 1-10 alkyl group)2, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, an amino group, a cyano group, -C(O)O-C 1-10 alkyl group, a carboxy group, a formyl group, a nitro group, and the like.

[0438] In formula (D-1), n 51 represents an integer of 0 or more. n 51 is preferably 1 or more, more preferably 2 or more, preferably 15 or less, more preferably 10 or less, and even more preferably 8 or less.

[0439] The active ester compound represented by formula (D-1) is preferably an active ester compound represented by the following formula (D-2).

[0440] [Chemical formula]

[0441] (In formula (D-2), Ar 61 each independently represents a monovalent aromatic group which may have a substituent; Ar 62 each independently represents a divalent aromatic group which may have a substituent; R 61 each independently represents a divalent hydrocarbon group which may have a substituent; Ar 61 , Ar 62 and R 61 do not contain a radical polymerizable group in any of them; n 61 represents an integer of 0 or more.)

[0442] In formula (D-2), Ar 61Each of these independently represents a monovalent aromatic group which may have substituents. 61 The range and preferred embodiments thereof are the Ar in formula (D-1). 51 It is the same as above. Also, in equation (D-2), Ar 62 Each of these independently represents a divalent aromatic group which may have substituents. 62 The range and preferred embodiments thereof are the Ar in formula (D-1). 52 It is the same as above. Also, in equation (D-2), R 61 Each of these independently represents a divalent hydrocarbon group which may have substituents. 61 The range and preferred embodiments thereof are R in formula (D-1) 51 It is similar to the above. Also, in equation (D-2), n 61 n represents a non-negative integer. 61 The range and preferred embodiments thereof are given by n in formula (D-1). 51 It is similar to that.

[0443] As mentioned earlier, Ar 61 Ar 62 and R 61 Each of these may have a substituent, but Ar 61 Ar 62 and R 61 None of these contain radical polymerizable groups. 61 Ar 62 and R 61 The substituents that each of them may have are, for example, Ar in formula (D-1). 51 Ar 52 Ar 53 and R 51 These are similar to the substituents that each of them may have.

[0444] A specific example of an active ester compound represented by formula (D-1) is the active ester compound represented by the following formula (Da). In formula (Da), n d This represents an integer greater than or equal to 0, and is preferably an integer between 0 and 6.

[0445] [ka]

[0446] Active ester resins that do not contain radical polymerizable groups may or may not contain the active ester compound represented by the following formula (D-3). Hereinafter, the active ester compound represented by the following formula (D-3) may be referred to as "component (D-3)".

[0447] [ka]

[0448] (In formula (D-3), n 71 Each of these independently represents an integer from 0 to 6; n 72 Each of these independently represents an integer from 1 to 5; n 73 Each of these independently represents an integer from 1 to 6.

[0449] From the viewpoint of significantly obtaining the desired effects of the present invention, the content of component (D-3) in the resin composition is preferably 5% by mass or less, more preferably 3% by mass or less, and even more preferably 1% by mass or less, based on 100% by mass of nonvolatile components in the resin composition. The lower limit of the content of component (D-3) may be 0% by mass or greater than 0% by mass. In particular, from the viewpoint of obtaining the desired effects of the present invention more significantly, the lower limit of the content of component (D-3) is more preferably closer to 0% by mass, and even more preferably 0% by mass. That is, in one preferred embodiment, the resin composition of the present invention does not contain the active ester compound represented by formula (D-3). In other words, in one preferred embodiment, the resin composition of the present invention excludes resin compositions containing the active ester compound represented by formula (D-3).

[0450] Examples of commercially available active ester resins that do not contain radical polymerizable groups include, for example, active ester resins containing a dicyclopentadiene-type diphenol structure such as "EXB9451", "EXB9460", "EXB9460S", "EXB-8000L", "EXB-8000L-65M", "EXB-8000L-65TM", "HPC-8000L-65TM", "HPC-8000L-65T", "HPC-8000", "HPC-8000-65T", and "EXB-8000H" (manufactured by DIC Corporation); and active ester resins containing a naphthalene structure such as "EXB-8100L-65T", "EXB-8150-60T", and "E Examples include "XB-8150-62T", "EXB-9416-70BK", "HPC-8150-62T", "EXB-8" (manufactured by DIC Corporation); "EXB9401" (manufactured by DIC Corporation) as a phosphorus-containing active ester resin; "DC808" (manufactured by Mitsubishi Chemical Corporation) as an active ester resin that is an acetylated phenol novolac; "YLH1026", "YLH1030", "YLH1048" (manufactured by Mitsubishi Chemical Corporation) as active ester resins that are benzoylated phenol novolacs; and "PC1300-02-65MA" (manufactured by Air Water Corporation) as an active ester resin containing a styryl group and a naphthalene structure.

[0451] As the carbodiimide resin, a resin having one or more, preferably two or more, carbodiimide structures in one molecule can be used. Carbodiimide resins can react with epoxy resins when combined with epoxy resins to cure the resin composition, and are therefore sometimes called "carbodiimide-based curing agents." Specific examples of carbodiimide resins include aliphatic biscarbodiimides (e.g., tetramethylene-bis(t-butylcarbodiimide), cyclohexanebis(methylene-t-butylcarbodiimide), etc.), aromatic biscarbodiimides (e.g., phenylene-bis(xylylcarbodiimide), etc.), and other biscarbodiimides; aliphatic polycarbodiimides (e.g., polyhexamethylenecarbodiimide, polytrimethylhexamethylenecarbodiimide, polycyclohexylenecarbodiimide, poly(methylenebiscyclohexylenecarbodiimide), poly(isophoronecarbodiimide), etc.), aromatic polycarbodiimides Polycarbodiimides such as poly(phenylenecarbodiimide), poly(naphthylenecarbodiimide), poly(trylenecarbodiimide), poly(methyldiisopropylphenylenecarbodiimide), poly(triethylphenylenecarbodiimide), poly(diethylphenylenecarbodiimide), poly(triisopropylphenylenecarbodiimide), poly(diisopropylphenylenecarbodiimide), poly(xylylenecarbodiimide), poly(tetramethylxylylenecarbodiimide), poly(methylenediphenylenecarbodiimide), poly[methylenebis(methylphenylene)carbodiimide], etc.) are examples. Examples of commercially available carbodiimide resins include "Carbodilite V-02B," "Carbodilite V-03," "Carbodilite V-04K," "Carbodilite V-05," "Carbodilite V-07," and "Carbodilite V-09" from Nisshinbo Chemical Co., Ltd.; and "Stavaxol P," "Stavaxol P400," and "Hycazil 510" from Lanxess Corporation. Carbodiimide resins may be used individually or in combination of two or more types.

[0452] (D) Other thermosetting resins may or may not contain aromatic diamine compounds containing ether bonds in their molecules as amine resins. Hereinafter, aromatic diamine compounds containing ether bonds in their molecules may be referred to as "component (D-4)".

[0453] Specific examples of component (D-4) include, for example, 1,3-bis(4-aminophenoxybenzene), 2,2-bis[4-(4-aminophenoxy)phenyl]propane, and 4,4'-diaminodiphenyl ether.

[0454] From the viewpoint of significantly obtaining the desired effects of the present invention, the content of component (D-4) in the resin composition is preferably 5% by mass or less, more preferably 3% by mass or less, and even more preferably 1% by mass or less, based on 100% by mass of nonvolatile components in the resin composition. The lower limit of the content of component (D-4) may be 0% by mass or greater than 0% by mass. In particular, from the viewpoint of obtaining the desired effects of the present invention more significantly, the lower limit of the content of component (D-4) is more preferably closer to 0% by mass, and even more preferably 0% by mass. That is, in a preferred embodiment, the resin composition of the present invention does not contain aromatic diamine compounds containing ether bonds in the molecule. In other words, in a preferred embodiment, the resin composition of the present invention excludes resin compositions containing aromatic diamine compounds containing ether bonds in the molecule.

[0455] The active group equivalent of component (D) is preferably 50 g / eq. or more, more preferably 100 g / eq. or more, preferably 3,000 g / eq. or less, more preferably 1,000 g / eq. or less, even more preferably 500 g / eq. or less, and even more preferably 300 g / eq. or less. The active group equivalent of component (D) is the mass of component (D) per equivalent of active group. Furthermore, the active group of component (D) represents a group that can react with the epoxy group of the epoxy resin, and varies depending on the type of component (D). For example, the active group of phenolic resin is a phenolic hydroxyl group. Also, for example, the active group equivalent of phenolic resin represents the phenolic hydroxyl group equivalent, and represents the mass of resin per equivalent of phenolic hydroxyl group.

[0456] The weight-average molecular weight (Mw) of component (D) is preferably 100 or more, more preferably 250 or more, even more preferably 400 or more, preferably 5,000 or less, more preferably 3,000 or less, and even more preferably 1,500 or less. The weight-average molecular weight of component (D) is the weight-average molecular weight on a polystyrene basis measured by gel permeation chromatography (GPC).

[0457] If the resin composition contains component (D), and component (D) contains an active ester resin that does not contain radical polymerizable groups, the ratio of components (A), (B), and (D) is ([total number of active ester groups in component (B)] + [total number of active ester groups in component (D)]) / [total number of epoxy groups in component (A)], preferably 0.01 or more, more preferably 0.1 or more, even more preferably 0.5 or more, preferably 10 or less, more preferably 5 or less, and even more preferably 3 or less. Here, the "total number of active ester groups in component (B)" and the "total number of epoxy groups in component (A)" are as described above. Furthermore, the "total number of active ester groups in component (D)" is the value obtained by dividing the mass of each component (D) (active ester resin that does not contain radical polymerizable groups) present in the resin composition by the equivalent amount of active ester groups of each component (D), and summing up all those values.

[0458] When the resin composition contains component (D), the ratio of components (A), (B), and (D) is ([total number of active ester groups of component (B)] + [total number of active groups of component (D)]) / [total number of epoxy groups of component (A)], preferably 0.01 or more, more preferably 0.1 or more, even more preferably 0.3 or more, preferably 10 or less, more preferably 5 or less, and even more preferably 3 or less. Here, the "total number of active ester groups of component (B)" and the "total number of epoxy groups of component (A)" are as described above. Furthermore, the "total number of active groups of component (D)" is the value obtained by dividing the mass of each component (D) present in the resin composition by the equivalent amount of active groups of each component (D), and summing up all those values.

[0459] If the resin composition contains (D) other thermosetting resins, the content of component (D) in the resin composition is preferably 1% by mass or more, more preferably 3% by mass or more, even more preferably 4.5% by mass or more, preferably 40% by mass or less, more preferably 35% by mass or less, even more preferably 30% by mass or less, or 27% by mass or less, based on 100% by mass of the resin components in the resin composition.

[0460] If the resin composition contains (D) other thermosetting resins, the content of component (D) in the resin composition is preferably 0.1% by mass or more, more preferably 0.5% by mass or more, even more preferably 1% by mass or more, preferably 20% by mass or less, more preferably 15% by mass or less, and even more preferably 10% by mass or less, based on 100% by mass of the nonvolatile components in the resin composition.

[0461] <(E) Inorganic filler> The resin composition of the present invention may contain (E) an inorganic filler as an optional component. The (E) inorganic filler as a component may be included in the resin composition in particulate form. The (E) inorganic filler may also be included in the cured product while maintaining its particulate form. The (E) inorganic filler may be used alone or in combination of two or more types.

[0462] Inorganic compounds can be used as materials for inorganic fillers. Examples of inorganic filler materials include silica, alumina, glass, cordierite, silicon oxide, barium sulfate, barium carbonate, talc, clay, mica powder, zinc oxide, hydrotalcite, boehmite, aluminum hydroxide, magnesium hydroxide, calcium carbonate, magnesium carbonate, magnesium oxide, boron nitride, aluminum nitride, manganese nitride, aluminum borate, strontium carbonate, strontium titanate, calcium titanate, magnesium titanate, bismuth titanate, titanium oxide, zirconium oxide, barium titanate, barium zirconate titanate, barium zirconate, calcium zirconate, zirconium phosphate, and zirconium tungstate phosphate. Among these, at least one inorganic compound selected from silica and alumina is preferred, with silica being particularly preferred. Examples of silica include amorphous silica, fused silica, crystalline silica, synthetic silica, and hollow silica. Spherical silica is also preferred as silica.

[0463] Examples of commercially available inorganic fillers include "SP60-05" and "SP507-05" from Nippon Steel Chemical & Material Co., Ltd.; "YC100C", "YA050C", "YA050C-MJE", "YA010C", "SC2500SQ", "SO-C4", "SO-C2", and "SO-C1" from Admatex Co., Ltd.; "UFP-30", "DAW-03", and "FB-105FD" from Denka Co., Ltd.; "Silfil NSS-3N", "Silfil NSS-4N", and "Silfil NSS-5N" from Tokuyama Corporation; "Cellspheres" and "MGH-005" from Taiheiyo Cement Corporation; and "Highpresica FH" from Ube Eximo Co., Ltd.

[0464] The average particle size of the inorganic filler is not particularly limited, but is preferably 1 μm or less, more preferably 0.7 μm or less, and even more preferably 0.5 μm or less. The lower limit of the average particle size is not particularly limited, but is preferably 0.01 μm or more, more preferably 0.03 μm or more, and even more preferably 0.05 μm or more. The average particle size of the inorganic filler can be measured by the laser diffraction-scattering method based on Mie scattering theory. Specifically, the particle size distribution of the inorganic filler can be created on a volume basis using a laser diffraction-scattering particle size distribution analyzer, and the average particle size can be measured by taking the median diameter as the average particle size. A sample can be used in which 100 mg of inorganic filler and 10 g of methyl ethyl ketone are weighed into a vial and dispersed using ultrasound for 10 minutes. The sample was measured using a laser diffraction-scattering particle size distribution analyzer with blue and red light source wavelengths, and the volume-based particle size distribution of the inorganic filler was measured using a flow cell method. The average particle size was calculated as the median diameter from the obtained particle size distribution. Examples of laser diffraction particle size distribution analyzers include the "LA-960" manufactured by Horiba, Ltd.

[0465] The specific surface area of ​​the inorganic filler is not particularly limited, but is preferably 0.1 m². 2 / g or more, more preferably 0.5m 2 / g or more, more preferably 1m 2 / g or more, 3m 2 / g or more or 5m 2 The specific surface area is 100 m² or more. The upper limit of the specific surface area is not particularly limited, but is preferably 100 m². 2 / g or less, more preferably 80m 2 / g or less, more preferably 60mg 2 / g or less, 50m 2 / g or less or 40m 2 The value is less than / g. The specific surface area of ​​the inorganic filler is obtained by adsorbing nitrogen gas onto the sample surface using a specific surface area measuring device (Macsorb HM-1210, manufactured by Mountec Co., Ltd.) according to the BET method, and then calculating the specific surface area using the BET multipoint method.

[0466] It is preferable that the inorganic filler is surface-treated with an appropriate surface treatment agent. Surface treatment can improve the moisture resistance and dispersibility of the inorganic filler. Examples of surface treatment agents include silane coupling agents such as vinyl-based silane coupling agents, epoxy-based silane coupling agents, styryl-based silane coupling agents, (meth)acrylic-based silane coupling agents, amino-based silane coupling agents, isocyanurate-based silane coupling agents, ureido-based silane coupling agents, mercapto-based silane coupling agents, isocyanate-based silane coupling agents, and acid anhydride-based silane coupling agents; non-silane coupling alkoxysilane compounds such as methyltrimethoxysilane and phenyltrimethoxysilane; and silazane compounds. The surface treatment agent may be used alone or in combination of two or more types.

[0467] Examples of commercially available surface treatment agents include "KBM403" (3-glycidoxypropyltrimethoxysilane), "KBM803" (3-mercaptopropyltrimethoxysilane), "KBE903" (3-aminopropyltriethoxysilane), "KBM573" (N-phenyl-3-aminopropyltrimethoxysilane), and "SZ-31" (hexamethyldisilazane), all manufactured by Shin-Etsu Chemical Co., Ltd.

[0468] From the viewpoint of improving the dispersibility of the inorganic filler, the degree of surface treatment by the surface treatment agent is preferably within a predetermined range. Specifically, it is preferable that 100% by mass of the inorganic filler is surface-treated with 0.2% to 5% by mass of the surface treatment agent.

[0469] The degree of surface treatment by a surface treatment agent can be evaluated by the amount of carbon per unit surface area of ​​the inorganic filler. From the viewpoint of improving the dispersibility of the inorganic filler, the amount of carbon per unit surface area of ​​the inorganic filler should be 0.02 mg / m². 2 The above is preferred, and 0.1 mg / m² 2 The above is more preferable, 0.2 mg / m² 2The above is even more preferable. On the other hand, the upper limit of the amount of carbon per unit surface area of ​​the inorganic filler is 1 mg / m², from the viewpoint of preventing an increase in the melt viscosity of the resin composition and the melt viscosity in sheet form. 2 The following is preferred: 0.8 mg / m² 2 The following is more preferable: 0.5 mg / m² 2 The following is even more preferable. The amount of carbon per unit surface area of ​​the inorganic filler can be measured after washing the inorganic filler with a solvent (e.g., methyl ethyl ketone (MEK)) after surface treatment. Specifically, a sufficient amount of MEK as the solvent is added to the inorganic filler that has been surface-treated with a surface treatment agent, and ultrasonic cleaning is performed at 25°C for 5 minutes. After removing the supernatant and drying the solids, the amount of carbon per unit surface area of ​​the inorganic filler can be measured using a carbon analyzer. As a carbon analyzer, the "EMIA-320V" manufactured by Horiba, Ltd. can be used.

[0470] (E) The inorganic filler may or may not contain (E-1) carbon-containing inorganic filler as component (E-1). Here, the range of carbon content of (E-1) carbon-containing inorganic filler is, for example, 0.1% by mass or more, preferably 0.2% by mass or more, more preferably 0.3% by mass or more, even more preferably 0.4% by mass or more, preferably 5% by mass or less, more preferably 3% by mass or less, and even more preferably 1% by mass or less, based on 100% by mass of the total amount of (E-1) carbon-containing inorganic filler. Note that the carbon content of (E-1) carbon-containing inorganic filler does not include the amount of carbon atoms that can be contained in a surface treatment agent that can be applied to the surface of component (E-1). Therefore, for example, the "carbon content" of (E-1) carbon-containing inorganic filler that has been surface-treated with a surface treatment agent containing carbon atoms does not include the amount of carbon atoms in the surface treatment agent.

[0471] The carbon content of (E-1) carbon-containing inorganic fillers can be measured by X-ray fluorescence analysis and solid-state NMR. For information on X-ray fluorescence analysis, see, for example, Kyushu University Central Analysis Center "Center News" vol.40 No.1, 2021 (published July 5, 2021). However, as mentioned above, the carbon content of (E-1) carbon-containing inorganic fillers does not include the amount of carbon atoms that the surface treatment agent may contain. Therefore, it is desirable to measure the carbon content of (E-1) carbon-containing inorganic fillers before surface treatment. For surface-treated (E-1) carbon-containing inorganic fillers, the amount of carbon atoms can be measured by, for example, performing chemical treatment with a strong acid and a strong base to dissolve the surface treatment agent together with the outermost layer of inorganic filler particles, and then performing the measurement.

[0472] (E-1) Carbon-containing inorganic fillers are typically particles that mainly contain inorganic compounds as materials for inorganic fillers. Therefore, (E-1) carbon-containing inorganic fillers may contain the above-mentioned inorganic compounds in combination with carbon. Among the above-mentioned inorganic compounds, silica is preferred from the viewpoint of exhibiting the desired effects of the present invention. Therefore, silica particles containing a specific range of carbon are preferred as (E-1) carbon-containing inorganic fillers. The amount of silica contained in the silica particles is preferably 60% by mass or more, more preferably 70% by mass or more, even more preferably 80% by mass or more, and even more preferably 90% by mass or more. The amount of silica can be measured by X-ray fluorescence analysis.

[0473] The method for producing the carbon-containing inorganic filler described above (E-1) is not particularly limited. From the viewpoint of energy saving, cost saving, and environmental protection, it is preferable to produce the carbon-containing inorganic filler (E-1) from plant materials. For example, plants of the Equisetaceae and Poaceae families may have the property of absorbing and accumulating silicon components from the soil. Therefore, silica can be produced as combustion ash by burning these plants (Japanese Patent Publication No. 6389349). Hereinafter, silica produced from plant materials in this way may be referred to as "biomass silica". Since biomass silica usually contains carbon, it can be used as a carbon-containing inorganic filler (E-1). In addition, commercially available carbon-containing inorganic fillers (E-1) may also be used. An example of a commercially available carbon-containing inorganic filler (E-1) is "Ethical Silica" (biomass silica produced from rice husks) manufactured by MIT.

[0474] From the viewpoint of significantly obtaining the desired effects of the present invention, the content of component (E-1) in the resin composition is preferably less than 10% by mass, more preferably 5% by mass or less, even more preferably 3% by mass or less, and even more preferably 1% by mass or less, based on 100% by mass of nonvolatile components in the resin composition. The lower limit of the content of component (E-1) may be 0% by mass or greater than 0% by mass. In particular, from the viewpoint of obtaining the desired effects of the present invention more significantly, the lower limit of the content of component (E-1) is more preferable as it approaches 0% by mass, and even more preferable to be 0% by mass. That is, in one preferred embodiment, the resin composition of the present invention does not contain (E-1) carbon-containing inorganic filler. In other words, in one preferred embodiment, the resin composition of the present invention excludes resin compositions containing (E-1) carbon-containing inorganic filler.

[0475] If the resin composition contains (E) an inorganic filler, the content of component (E) in the resin composition is preferably 40% by mass or more, more preferably 50% by mass or more, even more preferably 60% by mass or more, preferably 90% by mass or less, more preferably 80% by mass or less, even more preferably 75% by mass or less or 73% by mass or less, based on 100% by mass of the nonvolatile components in the resin composition.

[0476] <(F) Curing accelerator> The resin composition of the present invention may optionally contain (F) a curing accelerator. Unless otherwise specified, the curing accelerator as component (F) does not include components (A) to (E) described above. The curing accelerator (F) has the function of a catalyst for the reaction of thermosetting resins such as (A) epoxy resins and (B) activated ester resins containing radical polymerizable groups, and can therefore accelerate the curing of the resin composition. The curing accelerator (F) may be used alone or in combination of two or more types.

[0477] Examples of curing accelerators include imidazole-based curing accelerators, phosphorus-based curing accelerators, amine-based curing accelerators, guanidine-based curing accelerators, metal-based curing accelerators, and urea-based curing accelerators. When the resin composition contains (F) a curing accelerator, it is preferable that (F) a curing accelerator contains an imidazole-based curing accelerator.

[0478] Examples of imidazole-based curing accelerators include 2-methylimidazole, 2-undecylimidazole, 2-heptadecylimidazole, 1,2-dimethylimidazole, 2-ethyl-4-methylimidazole, 1,2-dimethylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 2-phenyl-4-methylimidazole, 1-benzyl-2-methylimidazole, and 1-benzyl-2-methylimidazole. Phenylimidazole, 1-cyanoethyl-2-methylimidazole, 1-cyanoethyl-2-undecylimidazole, 1-cyanoethyl-2-ethyl-4-methylimidazole, 1-cyanoethyl-2-phenylimidazole, 1-cyanoethyl-2-undecylimidazolium trimellitate, 1-cyanoethyl-2-phenylimidazolium trimellitate, 2,4-diamino-6-[2'-methylimidazolyl-( 1')-ethyl-s-triazine, 2,4-diamino-6-[2'-undecylimidazolyl-(1')]-ethyl-s-triazine, 2,4-diamino-6-[2'-ethyl-4'-methylimidazolyl-(1')]-ethyl-s-triazine, 2,4-diamino-6-[2'-methylimidazolyl-(1')]-ethyl-s-triazine isocyanurate adduct, 2-phenylimidazole isocyanurate adduct, 2 Examples include imidazole compounds such as phenyl-4,5-dihydroxymethylimidazole, 2-phenyl-4-methyl-5-hydroxymethylimidazole, 2,3-dihydro-1H-pyrrolo[1,2-a]benzimidazole, 1-dodecyl-2-methyl-3-benzylimidazolium chloride, 2-methylimidazoline, and 2-phenylimidazoline, as well as adducts of these imidazole compounds with epoxy resins. Among these, the imidazole-based curing accelerator is preferably at least one imidazole compound selected from 2-ethyl-4-methylimidazole and 1-benzyl-2-phenylimidazole.Commercial imidazole-based curing accelerators may be used, for example, "P200-H50" from Mitsubishi Chemical Corporation; and "Curesol 2MZ", "2E4MZ", "Cl1Z", "Cl1Z-CN", "Cl1Z-CNS", "Cl1Z-A", "2MZ-OK", "2MA-OK", "2MA-OK-PW", "2MZA-PW", "2PHZ", "2PHZ-PW", "2P4MZ", "1B2PZ", and "1B2PZ-10M" from Shikoku Chemicals, Inc.

[0479] If the resin composition contains a curing accelerator (F), the content of component (F) in the resin composition is preferably 0.1% by mass or more, more preferably 0.3% by mass or more, even more preferably 0.5% by mass or more or 0.6% by mass or more, preferably 5% by mass or less, more preferably 3% by mass or less, even more preferably 1% by mass or less or 0.9% by mass or less, based on 100% by mass of the resin components in the resin composition.

[0480] If the resin composition contains a curing accelerator (F), the content of component (F) in the resin composition is preferably 0.01% by mass or more, more preferably 0.1% by mass or more, even more preferably 0.2% by mass or more, preferably 1% by mass or less, more preferably 0.5% by mass or less, and even more preferably 0.3% by mass or less, based on 100% by mass of the nonvolatile components in the resin composition.

[0481] <(G)Organic filler> The resin composition of the present invention may contain (G) an organic filler as an optional component. Unless otherwise specified, the (G) organic filler does not include components (A) to (F) described above. The (G) organic filler may be included in the resin composition in a granular state and is not miscible with resin components other than the (G) organic filler. Furthermore, the (G) organic filler may be included in the cured product while maintaining its granular form. The (G) organic filler may be used alone or in combination of two or more types.

[0482] (G) Examples of organic fillers include rubber particles, polyamide fine particles, silicone particles, and core-shell type particles. When the resin composition contains (G) organic fillers, it is preferable that (G) organic fillers contain rubber particles.

[0483] Examples of rubber components included in rubber particles include olefin-based thermoplastic elastomers such as polybutadiene, polyisoprene, polychlorobutadiene, ethylene-vinyl acetate copolymer, styrene-butadiene copolymer, styrene-isoprene copolymer, styrene-isobutylene copolymer, acrylonitrile-butadiene copolymer, isoprene-isobutylene copolymer, isobutylene-butadiene copolymer, ethylene-propylene-diene terpolymer, and ethylene-propylene-butene terpolymer; and acrylic-based thermoplastic elastomers such as propyl poly(meth)acrylate, butyl poly(meth)acrylate, cyclohexyl poly(meth)acrylate, and octyl poly(meth)acrylate. Preferably, the rubber component included in the rubber particles is an olefin-based thermoplastic elastomer, and more preferably, a styrene-butadiene copolymer. Furthermore, silicone-based rubbers such as polyorganosiloxane rubber may be mixed into the rubber component included in the rubber particles. The rubber component contained in the rubber particles has a glass transition temperature of, for example, 0°C or lower, preferably -10°C or lower, more preferably -20°C or lower, and even more preferably -30°C or lower.

[0484] Commercially available rubber particles may be used, such as "EXL2655" from Dow Chemical Japan, or "AC3401N" and "AC3816N" from Aica Kogyo Co., Ltd.

[0485] If the resin composition contains (G) an organic filler, the content of component (G) in the resin composition is preferably 0.1% by mass or more, more preferably 1% by mass or more, even more preferably 2% by mass or more, preferably 10% by mass or less, more preferably 7% by mass or less, even more preferably 5% by mass or less or 4% by mass or less, based on 100% by mass of the resin components in the resin composition.

[0486] If the resin composition contains (G) an organic filler, the content of component (G) in the resin composition is preferably 0.1% by mass or more, more preferably 0.5% by mass or more, even more preferably 0.8% by mass or more, preferably 5% by mass or less, more preferably 3% by mass or less, and even more preferably 1% by mass or less, based on 100% by mass of the nonvolatile components in the resin composition.

[0487] <(H)Thermoplastic resin> The resin composition of the present invention may contain (H) thermoplastic resin as an optional component. Unless otherwise specified, the (H) thermoplastic resin as component (H) does not include components (A) to (G) described above. The (H) thermoplastic resin may be compatible with resin components other than the (H) thermoplastic resin and be included in the resin composition. The (H) thermoplastic resin may be used alone or in combination of two or more types.

[0488] Examples of (H) thermoplastic resins include phenoxy resin, polystyrene resin, polyvinyl acetal resin, polyolefin resin, polybutadiene resin, polyamide-imide resin, polyetherimide resin, polysulfone resin, polyethersulfone resin, polyphenylene ether resin, polycarbonate resin, polyetheretherketone resin, polyester resin, etc. When the resin composition contains (H) thermoplastic resin, it is preferable that (H) thermoplastic resin contains phenoxy resin.

[0489] Examples of phenoxy resins include phenoxy resins having one or more skeletons selected from the group consisting of bisphenol A skeleton, bisphenol F skeleton, bisphenol S skeleton, bisphenolacetophenone skeleton, novolac skeleton, biphenyl skeleton, fluorene skeleton, dicyclopentadiene skeleton, norbornene skeleton, naphthalene skeleton, anthracene skeleton, adamantane skeleton, terpene skeleton, and trimethylcyclohexane skeleton. The terminal end of the phenoxy resin may be any functional group such as a phenolic hydroxyl group or an epoxy group. Specific examples of phenoxy resins include "1256" and "4250" (both phenoxy resins containing a bisphenol A skeleton) manufactured by Mitsubishi Chemical Corporation; "YX8100" (phenoxy resin containing a bisphenol S skeleton) manufactured by Mitsubishi Chemical Corporation; "YX6954" (phenoxy resin containing a bisphenol acetophenone skeleton) manufactured by Mitsubishi Chemical Corporation; "FX280" and "FX293" manufactured by Nippon Steel Chemical & Material Co., Ltd.; and "YL7500BH30", "YX6954BH30", "YX7553", "YX7553BH30", "YL7769BH30", "YL6794", "YL7213", "YL7290", "YL7482", "YL7891BH30", and "YX7891T30" manufactured by Mitsubishi Chemical Corporation. Phenoxy resins may be used individually or in combination of two or more types.

[0490] The phenoxy resin may or may not contain a phenoxy resin represented by the following formula (H-1) with a weight-average molecular weight of 10,000 to 20,000. Hereinafter, the phenoxy resin represented by the following formula (H-1) with a weight-average molecular weight of 10,000 to 20,000 may be referred to as "component (H-1)".

[0491] [ka]

[0492] (In formula (H-1), X 81 Each of these independently represents a divalent group containing an aromatic ring substituted with at least one alkenyl group; Y 81 Each of these independently represents a hydrogen atom, an acyl group with 2 to 21 carbon atoms, or a glycidyl group; Z 81 Each of these independently represents a hydrogen atom or an acyl group with 2 to 21 carbon atoms, and all Z 81 More than 5 mole% of the composition consists of acyl groups with 2 to 21 carbon atoms; n 81 (This represents a repeating number, and its average value is between 15 and 500.)

[0493] In equation (H-1), X 81 Each of these independently represents a divalent group containing an aromatic ring substituted with at least one alkenyl group. 81 The aromatic ring contained therein, which is substituted with at least one alkenyl group, is, for example, X in formula (Bv) above. 51 This is similar to the aromatic ring Bv containing the divalent group represented by . As mentioned above, the aromatic ring Bv may have further substituents other than alkenyl groups, as long as at least one alkenyl group is substituted. Examples of substituents other than alkenyl groups that the aromatic ring Bv may have include alkyl groups having 1 to 12 carbon atoms, alkoxy groups having 1 to 12 carbon atoms, aryl groups having 6 to 12 carbon atoms, etc. Examples of alkenyl groups that the aromatic ring Bv may have include alkenyl groups having 3 to 12 carbon atoms.

[0494] In equation (H-1), X 81 It may further contain components other than the aromatic ring Bv, insofar as it contains the aromatic ring Bv and forms a divalent group. In one embodiment, X 81 It consists of a group made up of an aromatic ring Bv and other divalent groups X 82 It may also contain other divalent groups X 82 For example, X in the above equation (Bv) 51 The divalent group represented by "X" may contain "other divalent groups X 82 It is similar to the above.

[0495] In equation (H-1), Y81 Each of these independently represents a hydrogen atom, an acyl group with 2 to 21 carbon atoms, or a glycidyl group. Here, Y 81 The number of carbon atoms in an acyl group that can be represented includes the carbon atoms of the carbonyl group that constitutes the acyl group.

[0496] Y 51 The acyl group having 2 to 21 carbon atoms that can be represented by this can be a monovalent group in which a monovalent hydrocarbon group such as an alkyl group, aryl group, or aralkyl group is bonded to a carbonyl group (-CO-). 51 The acyl group having 2 to 21 carbon atoms that can be represented is preferably a monovalent group in which an alkyl group having 1 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, or an aralkyl group having 7 to 13 carbon atoms is bonded to the carbonyl group (-CO-), more preferably an acetyl group, a propanoyl group, a butanoyl group, a benzoyl group, or a methylbenzoyl group, and even more preferably an acetyl group or a benzoyl group.

[0497] In equation (H-1), Z 81 Each of these independently represents either a hydrogen atom or an acyl group with 2 to 21 carbon atoms. Here, Z 81 The number of carbon atoms in an acyl group that can be represented is Y 81 Similar to the number of carbon atoms in the acyl group that can be represented, this includes the carbon atoms of the carbonyl group that constitutes the acyl group. 81 The acyl groups with 2 to 21 carbon atoms that can be represented are, for example, the above-mentioned Y 81 This is similar to the acyl group with 2 to 21 carbon atoms that can be represented.

[0498] Furthermore, in equation (H-1), all Z 81 The proportion of "acyl groups with 2 to 21 carbon atoms" is in the range of 5 mol% or more, preferably 10 mol% or more, more preferably 20 mol% or more, even more preferably 50 mol% or more, and even more preferably 70 mol% or more. 81The upper limit of the proportion of "acyl groups with 2 to 21 carbon atoms" in the mixture may be 100 mol%, or it may be less than 100 mol% (for example, 97 mol% or less, 96 mol% or less, or 95 mol% or less, etc.).

[0499] In equation (H-1), n 81 n represents a repeating number, and its average value is a number between 15 and 500. 81 The average value (numerical mean) is preferably 17 or more and 400 or less, and more preferably 20 or more and 300 or less. 81 The value can be calculated using the number-average molecular weight (Mn) in terms of polyethylene oxide, measured by gel permeation chromatography (GPC).

[0500] The weight-average molecular weight (Mw) of component (H-1) is preferably 15,000 to 150,000, more preferably 20,000 to 100,000, and even more preferably 20,000 to 50,000.

[0501] Note that the weight-average molecular weight (Mw) of component (H-1) is the weight-average molecular weight in terms of polyethylene oxide, measured by gel permeation chromatography (GPC), and may differ from the weight-average molecular weight of the thermoplastic resin (H) in terms of polystyrene, which will be described later. Specifically, in the measurement procedure for the weight-average molecular weight (Mw) of component (H-1), a high-speed GPC instrument "HLC8320GPC" manufactured by Tosoh Corporation is used, equipped with columns (for example, "TSKgel SuperH-H", "SuperH2000", "SuperHM-H", etc., manufactured by Tosoh Corporation) in series, and the column temperature is set to 40°C. In addition, tetrahydrofuran (THF) is used as the eluent at a flow rate of 1 mL / min, and a differential refractive index detector is used. For the measurement sample, 0.1 g of the solid content to be measured is dissolved in 10 mL of THF, filtered through a 0.45 μm microfilter, and 20 μL of this sample can be used. The weight-average molecular weight (Mw) is calculated by converting from a calibration curve obtained from standard polyethylene oxides (for example, "SE-2", "SE-5", "SE-8", "SE-15", "SE-30", "SE-70", and "SE-150" manufactured by Tosoh Corporation). For data processing of the measurement of the weight-average molecular weight (Mw) of component (H-1), Tosoh Corporation's dedicated GPC analysis program, "GPC8020 Model II Version 6.00", can be used.

[0502] From the viewpoint of significantly obtaining the desired effects of the present invention, the content of component (H-1) in the resin composition is preferably 5% by mass or less, more preferably 3% by mass or less, and even more preferably 1% by mass or less, based on 100% by mass of nonvolatile components in the resin composition. The lower limit of the content of component (H-1) may be 0% by mass or greater than 0% by mass. In particular, from the viewpoint of obtaining the desired effects of the present invention more significantly, the lower limit of the content of component (H-1) is more preferably closer to 0% by mass, and even more preferably 0% by mass. That is, in a preferred embodiment, the resin composition of the present invention does not contain a phenoxy resin represented by formula (H-1) and having a weight-average molecular weight of 10,000 to 20,000 (wherein the weight-average molecular weight of the phenoxy resin is the weight-average molecular weight on a polyethylene oxide basis). In other words, in one preferred embodiment, the resin composition of the present invention excludes resin compositions containing a phenoxy resin represented by formula (H-1) and having a weight-average molecular weight of 10,000 to 20,000 (wherein the weight-average molecular weight of the phenoxy resin is the weight-average molecular weight on a polyethylene oxide basis).

[0503] (H) The weight-average molecular weight (Mw) of the thermoplastic resin is preferably 5,000 or more, more preferably 8,000 or more, even more preferably 10,000 or more, 15,000 or more, or 20,000 or more, preferably 200,000 or less, more preferably 150,000 or less, or 100,000 or less, even more preferably 80,000 or less, or 60,000 or less. (H) The weight-average molecular weight of the thermoplastic resin is the weight-average molecular weight on a polystyrene basis measured by gel permeation chromatography (GPC).

[0504] When the resin composition contains a thermoplastic resin (H), the content of component (H) in the resin composition is preferably 0.1% by mass or more, more preferably 0.3% by mass or more, even more preferably 0.5% by mass or more or 0.7% by mass or more, preferably 5% by mass or less, more preferably 3% by mass or less, and even more preferably 1% by mass or less, based on 100% by mass of the resin components in the resin composition.

[0505] When the resin composition contains a thermoplastic resin (H), the content of component (H) in the resin composition is preferably 0.01% by mass or more, more preferably 0.1% by mass or more, even more preferably 0.2% by mass or more, preferably 1% by mass or less, more preferably 0.5% by mass or less, and even more preferably 0.3% by mass or less, based on 100% by mass of the nonvolatile components in the resin composition.

[0506] <(I) Other additives> The resin composition of the present invention may further contain, in combination with components (A) to (H) described above, any other additive (I). This other additive (I) as component (I) does not include any of the components (A) to (H) described above.

[0507] (I) Other additives include, for example, radical polymerization initiators such as peroxide-based radical polymerization initiators and azo-based radical polymerization initiators; organometallic compounds such as organocopper compounds and organozinc compounds; colorants such as phthalocyanine blue, phthalocyanine green, iodine green, diazo yellow, crystal violet, titanium dioxide, and carbon black; polymerization inhibitors such as hydroquinone, catechol, pyrogallol, and phenothiazine; leveling agents such as silicone-based leveling agents and acrylic polymer-based leveling agents; thickeners such as bentonite and montmorillonite; defoamers such as silicone-based defoamers, acrylic-based defoamers, fluorine-based defoamers, and vinyl resin-based defoamers; ultraviolet absorbers such as benzotriazole-based ultraviolet absorbers; and urea. Examples include adhesion improvers such as silanes; adhesion ferrants such as triazole-based adhesion ferrants, tetrazole-based adhesion ferrants, and triazine-based adhesion ferrants; antioxidants such as hindered phenol-based antioxidants; fluorescent whitening agents such as stilbene derivatives; surfactants such as fluorine-based surfactants and silicone-based surfactants; flame retardants such as phosphorus-based flame retardants (e.g., phosphate ester compounds, phosphazene compounds, phosphinic acid compounds, red phosphorus), nitrogen-based flame retardants (e.g., melamine sulfate), halogen-based flame retardants, and inorganic flame retardants (e.g., antimony trioxide); stabilizers such as borate-based stabilizers, titanate-based stabilizers, aluminate-based stabilizers, zirconate-based stabilizers, isocyanate-based stabilizers, carboxylic acid-based stabilizers, and carboxylic acid anhydride-based stabilizers; and so on. (I) Other additives may be used individually or in combination of two or more types. When the resin composition contains (I) other additives, the content of component (I) in the resin composition may be determined according to the properties required for the resin composition. Furthermore, components (A) to (H) described above may have functions such as radical polymerization initiators, organometallic compounds, colorants, polymerization inhibitors, leveling agents, thickeners, defoamers, ultraviolet absorbers, adhesion enhancers, adhesion imparters, antioxidants, fluorescent whitening agents, surfactants, flame retardants, dispersants, and stabilizers. In such cases, such components shall be considered as components (A) to (H) described above, rather than as component (I).

[0508] <(J) Organic Solvents> The resin composition of the present invention may further contain an optional volatile component, (J) an organic solvent, in combination with the non-volatile components such as components (A) to (I) described above. Examples of organic solvents include: ketone solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone; ester solvents such as methyl acetate, ethyl acetate, butyl acetate, isobutyl acetate, isoamyl acetate, methyl propionate, ethyl propionate, and γ-butyrolactone; ether solvents such as tetrahydropyran, tetrahydrofuran, 1,4-dioxane, diethyl ether, diisopropyl ether, dibutyl ether, diphenyl ether, and anisole; alcohol solvents such as methanol, ethanol, propanol, butanol, and ethylene glycol; and 2-ethoxyethyl acetate, propylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, ethyl diglycol acetate, γ-butyrolactone, and methyl methoxypropionate. Examples include ether ester solvents such as methyl lactate, ethyl lactate, and methyl 2-hydroxyisobutyrate; ether alcohol solvents such as 2-methoxypropanol, 2-methoxyethanol, 2-ethoxyethanol, propylene glycol monomethyl ether, and diethylene glycol monobutyl ether (butyl carbitol); amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methyl-2-pyrrolidone; sulfoxide solvents such as dimethyl sulfoxide; nitrile solvents such as acetonitrile and propionitrile; aliphatic hydrocarbon solvents such as hexane, cyclopentane, cyclohexane, and methylcyclohexane; and aromatic hydrocarbon solvents such as benzene, toluene, xylene, ethylbenzene, and trimethylbenzene. (J) Organic solvents may be used individually or in combination of two or more types.

[0509] If the resin composition contains (J) an organic solvent, the content of component (J) in the resin composition may be, for example, 60% by mass or less, 40% by mass or less, 30% by mass or less, 20% by mass or less, or 15% by mass or less, based on 100% by mass of all components of the resin composition. Alternatively, the content of (J) an organic solvent in the resin composition may be 0% by mass.

[0510] [Method for producing resin composition] The resin composition of the present invention can be produced, for example, by mixing components that may be included in the resin composition. Therefore, the resin composition can be produced by a production method that includes the step of mixing (A) an epoxy resin, (B) an active ester resin containing a radical polymerizable group, and (C) a resin containing an imide bond. This production method may also include the step of mixing any components such as components (D) to (J). Components (A) to (J) may be mixed partially or entirely at the same time, or they may be mixed sequentially. Furthermore, this production method may, if necessary, include kneading or stirring (mixing) the resin composition using kneading means such as a three-roll mill, ball mill, bead mill, or sand mill, or stirring means such as a super mixer, planetary mixer, or high-speed rotary mixer.

[0511] The method for producing the resin composition of the present invention is not particularly limited and may include a first step of reacting component (A-1) and component (B) to obtain a reactant having a weight-average molecular weight of 10,000 to 200,000, and a second step of mixing the obtained reactant with component (C), or it may not include the above first and second steps. In other words, embodiments including the above first and second steps can be excluded from the method for producing the resin composition of the present invention.

[0512] Note that the weight-average molecular weight (Mw) of the reactant obtained by reacting component (A-1) and component (B) is the weight-average molecular weight in terms of polyethylene oxide measured by gel permeation chromatography (GPC), and may differ from the weight-average molecular weight in terms of polystyrene. Specifically, in the measurement procedure for the weight-average molecular weight (Mw) of the reactant obtained by reacting component (A-1) and component (B), a high-speed GPC instrument "HLC8320GPC" manufactured by Tosoh Corporation is used, equipped with a column (for example, "TSKgel SuperH-H", "SuperH2000", "SuperHM-H", "SuperHM-H", etc. manufactured by Tosoh Corporation) in series, and the column temperature is set to 40°C. In addition, tetrahydrofuran (THF) is used as the eluent at a flow rate of 1 mL / min, and a differential refractive index detector is used. For the measurement sample, 0.1 g of the solid content to be measured is dissolved in 10 mL of THF, filtered through a 0.45 μm microfilter, and 20 μL of this sample can be used. The weight-average molecular weight (Mw) is calculated by converting from a calibration curve obtained using standard polyethylene oxides (for example, "SE-2", "SE-5", "SE-8", "SE-15", "SE-30", "SE-70", and "SE-150" manufactured by Tosoh Corporation). For data processing of the weight-average molecular weight (Mw) of the reactant obtained by reacting component (A-1) and component (B), Tosoh Corporation's dedicated GPC analysis program, "GPC8020 Model II Version 6.00", can be used.

[0513] [Properties of resin compositions] The resin composition of the present invention comprises (A) an epoxy resin, (B) an active ester resin containing a radical polymerizable group, and (C) a resin containing an imide bond (and optionally (D) other thermosetting resins, (E) inorganic fillers, (F) curing accelerators, (G) organic fillers, (H) thermoplastic resins, (I) other additives, and (J) organic solvents). Furthermore, the epoxy resin (A) includes (A-1) a liquid epoxy resin having a viscosity of 100 mPa·s or more at 25°C, and the resin containing an imide bond (C) includes at least one of (C-1) a maleimide resin and (C-2) a polyimide resin. In addition, the resin composition is characterized in that the total amount of component (C-1) and component (C-2) is 6% by mass or more and 20% by mass or less based on 100% by mass of the resin components in the resin composition. Such a resin composition can produce a cured product with a low coefficient of linear thermal expansion. Furthermore, since such resin compositions can suppress the residual curing stress during curing, they can suppress delamination due to the fracture of the cured resin composition.

[0514] The resin composition of the present invention is characterized by producing a cured product with a low coefficient of linear thermal expansion. Therefore, when an insulating layer is formed using the resin composition of the present invention, warping of the insulating layer can be reduced. For example, as described in the section "Test Example 1: Measurement of the Coefficient of Linear Thermal Expansion (CTE) of the Cured Product" below, when thermomechanical analysis is performed on a cured product obtained by curing a resin composition with a thickness of 40 μm using the tensile load method, the average coefficient of linear thermal expansion from 25°C to 150°C is preferably less than 35 ppm / °C, more preferably 30 ppm / °C or less, and even more preferably 25 ppm / °C or less. The lower limit of the average coefficient of linear thermal expansion that can be measured under such conditions is not particularly limited, but may be 1 ppm / °C or more, 2 ppm / °C or more, 3 ppm / °C or more, etc.

[0515] The resin composition of the present invention can suppress the residual curing stress during the curing of the resin composition. Therefore, when an insulating layer is formed using the resin composition of the present invention, delamination due to the fracture of the cured resin composition can be suppressed. For example, as described in the section "Test Example 5: Evaluation of Delamination of Cured Resin Composition" below, layers made of cured resin composition are formed on both sides of an inner layer substrate in which equilateral triangular copper pads with sides of 1 mm are formed in a grid pattern at 500 μm intervals. Next, via holes are formed in the layer made of cured material and a roughening treatment is performed. In two copper pads after the roughening treatment (a total of 6 vertices of the equilateral triangle), the delamination rate (%) of the layer made of cured material can be preferably 33% or less, more preferably 17% or less, and even more preferably 0%.

[0516] The resin composition of the present invention can yield a cured product exhibiting excellent mechanical strength. Therefore, the cured product of the resin composition of the present invention can have high rigidity and toughness. For example, when a 1 mm diameter needle is pierced into an evaluation cured product obtained by curing the resin composition of the present invention at 190°C for 90 minutes at a curing condition of 50 mm / min, the strength at the time of fracture of the evaluation cured product pierced by the needle (piercing strength) is preferably 0.7 N or more, more preferably 0.9 N or more, even more preferably 1 N or more, 1.1 N or more, 1.2 N or more, 1.3 N or more, 1.4 N or more, 1.5 N or more, or 1.6 N or more. The upper limit of the piercing strength is preferably higher, for example, it may be 10 N or less. The piercing strength can be measured according to the method described in the section "<Test Example 2: Stab Test of Cured Product>" described later.

[0517] As described above, the resin composition of the present invention can suppress the residual curing stress during the curing of the resin composition. Therefore, the resin composition of the present invention may have the characteristic of being able to suppress a rapid curing reaction during the curing of the resin composition. For example, as described in the section <Test Example 3: Evaluation of Reactivity> below, differential scanning calorimetry is performed using 10 mg of the resin composition of the present invention at a heating rate of 5 °C / min in a temperature range of 25 °C to 300 °C. In such measurement, the reaction initiation temperature based on differential scanning calorimetry is preferably 95 °C or higher, more preferably 100 °C or higher, 105 °C or higher, or 110 °C or higher. The upper limit of the reaction initiation temperature can be, for example, 150 °C or lower. When the reaction initiation temperature is within the above range, the rapid curing reaction can be further suppressed, and thus delamination due to the fracture of the cured resin composition can be further suppressed.

[0518] Furthermore, in the differential scanning calorimetry described above, if the reaction start temperature based on differential scanning calorimetry is T1 (°C) and the reaction peak temperature based on differential scanning calorimetry is T2 (°C), then the temperature difference T2-T1 is preferably 62°C or higher, more preferably 64°C or higher, and even more preferably 65°C or higher or 70°C or higher. The upper limit of the temperature difference T2-T1 can be, for example, 150°C or lower. When the temperature difference T2-T1 is within the above preferred range, residual stress during curing can be further suppressed, and thus delamination due to fracture of the cured resin composition can be further suppressed. In addition, when the temperature difference T2-T1 is within the above preferred range, delamination due to fracture of the cured resin composition can be further suppressed, and the occurrence of cracks after roughening treatment in the cured resin composition can be suppressed.

[0519] The reaction start temperature and the reaction peak temperature, and the difference between the start temperature and the reaction peak temperature, can be adjusted, for example, by the composition of the resin composition. Specifically, this can be adjusted by combining components (A-1) and (B) as component (A), and specific amounts of component (C-1) and / or component (C-2) as component (C).

[0520] The resin composition of the present invention can produce a cured product that can suppress the occurrence of cracks after roughening treatment. Therefore, when an insulating layer is formed using the resin composition of the present invention, an insulating layer with excellent crack resistance can be obtained. For example, as described in the section "Test Example 4: Evaluation of Crack Resistance" below, layers made of the cured resin composition are formed on both sides of an inner layer substrate in which circular copper pads with a diameter of 350 μm are formed in a grid pattern at 400 μm intervals so that the residual copper ratio is 60%. Next, the layers made of the cured product are subjected to roughening treatment. When 100 copper pad portions are observed after roughening treatment, the number of cracks that occur in the layers made of the cured product is preferably 10 or less, more preferably 5 or less, and even more preferably 0.

[0521] [Uses of resin compositions] As described above, the resin composition of the present invention yields a cured product with a low coefficient of linear thermal expansion, and can suppress delamination due to the fracture of the cured product. Therefore, the resin composition of the present invention can be suitably used as a resin composition for forming an insulating layer of a printed wiring board (resin composition for the insulating layer of a printed wiring board), and can be suitably used as a resin composition for forming an interlayer insulating layer of a printed wiring board (resin composition for the interlayer insulating layer of a printed wiring board). The resin composition of the present invention can also be suitably used when the printed wiring board is a circuit board with embedded components. The resin composition of the present invention can also be suitably used as a resin composition for forming an insulating layer of a redistribution substrate for a semiconductor package (resin composition for the insulating layer of a redistribution substrate). In this invention, printed wiring boards and redistribution substrates are collectively referred to as "circuit boards," and therefore the resin composition of the present invention can be suitably used for the insulating layer of a circuit board.

[0522] The resin composition of the present invention can be used in a wide range of applications where a resin composition is required, such as sheet-like laminated materials like resin sheets and prepregs, solder resists, underfill materials, die bonding materials, hole-filling resins, sealing resins, and component embedding resins.

[0523] [Sheet-like laminated materials (resin sheets, prepregs)] The resin composition of the present invention can be used as is, or it may be used in the form of a sheet-like laminated material containing the resin composition.

[0524] Since the resin composition of the present invention can exhibit good flexibility before curing, the following resin sheets and prepregs are preferred as sheet-like laminated materials.

[0525] In one embodiment, the resin sheet comprises a support and a layer of a resin composition provided on the support (hereinafter simply referred to as the "resin composition layer"), wherein the resin composition layer is formed from the resin composition of the present invention.

[0526] The optimal thickness of the resin composition layer varies depending on the application and may be determined appropriately according to the application. For example, from the viewpoint of thinning printed circuit boards and semiconductor packages, the thickness of the resin composition layer is preferably 100 μm or less, 80 μm or less, 60 μm or less, 50 μm or less, 40 μm or less, or 30 μm or less. The lower limit of the thickness of the resin composition layer is not particularly limited, but can usually be 1 μm or more, 5 μm or more, etc.

[0527] Examples of support materials include thermoplastic resin films, metal foils, and release paper, with thermoplastic resin films and metal foils being preferred. Therefore, in one preferred embodiment, the support material is a thermoplastic resin film or a metal foil.

[0528] When using a thermoplastic resin film as a support, examples of thermoplastic resins include polyester resins such as polyethylene terephthalate (PET) and polyethylene naphthalate (PEN); polycarbonate (PC); acrylic resins such as polymethyl methacrylate (PMMA); cyclic polyolefins; triacetylcellulose (TAC); polyether sulfide (PES); polyether ketones; and polyimides. Among these, polyester resins are preferred, polyethylene terephthalate or polyethylene naphthalate are more preferred, and inexpensive polyethylene terephthalate is particularly preferred.

[0529] When using metal foil as a support, examples of metal foil include copper foil and aluminum foil, with copper foil being preferred. As for copper foil, foil made of single-metal copper may be used, or foil made of an alloy of copper with another metal (for example, tin, chromium, silver, magnesium, nickel, zirconium, silicon, titanium, etc.) may be used.

[0530] The support may have a matte finish, corona treatment, or antistatic treatment applied to the surface that bonds with the resin composition layer. Alternatively, a support with a release layer may be used, which has a release layer on the surface that bonds with the resin composition layer. Examples of release agents used in the release layer of the support with a release layer include one or more release agents selected from the group consisting of alkyd resins, polyolefin resins, urethane resins, and silicone resins. Examples of commercially available release agents include "SK-1", "AL-5", and "AL-7" from Lintec Corporation. Furthermore, commercially available support with a release layer may also be used, for example, "Purex" from Toyobo Co., Ltd. and "Unipeel" from Unitika Corporation, which are PET films having a release layer mainly composed of alkyd resin-based release agents or polyolefin resin-based release agents.

[0531] The thickness of the support is not particularly limited, but is preferably in the range of 5 μm to 75 μm, and more preferably in the range of 10 μm to 60 μm. When using a support with a release layer, it is preferable that the overall thickness of the support with the release layer is within the above range.

[0532] When using metal foil as a support, a metal foil with a support substrate, which is formed by laminating a peelable support substrate onto a thin metal foil, may be used. In one embodiment, the metal foil with a support substrate includes a support substrate, a release layer provided on the support substrate, and a metal foil provided on the release layer. When using metal foil with a support substrate as a support, the resin composition layer is provided on the metal foil.

[0533] In a metal foil with a support substrate, the material of the support substrate is not particularly limited, but examples include copper foil, aluminum foil, stainless steel foil, titanium foil, copper alloy foil, etc. When copper foil is used as the support substrate, it may be electrolytic copper foil or rolled copper foil. Furthermore, the release layer is not particularly limited as long as it can be used to peel the metal foil from the support substrate, and examples include an alloy layer of elements selected from the group consisting of Cr, Ni, Co, Fe, Mo, Ti, W, and P; an organic coating, etc.

[0534] In a metal foil with a support substrate, the material of the metal foil is preferably, for example, copper foil or copper alloy foil.

[0535] In a metal foil with a support substrate, the thickness of the support substrate is not particularly limited, but is preferably in the range of 10 μm to 150 μm, and more preferably in the range of 10 μm to 100 μm. The thickness of the metal foil may be, for example, in the range of 0.1 μm to 10 μm.

[0536] In one embodiment, the resin sheet may further include any additional layer as needed. Such an additional layer may be, for example, a protective film provided on the side of the resin composition layer that is not bonded to the support (i.e., the side opposite to the support). The thickness of the protective film is not particularly limited, but is, for example, 1 μm to 75 μm, preferably 1 μm to 40 μm. By laminating the protective film, the adhesion of dust and other debris to the surface of the resin composition layer and scratches can be suppressed.

[0537] Resin sheets can be manufactured, for example, by using a liquid resin composition as is, or by preparing a resin varnish by dissolving the resin composition in an organic solvent, applying the prepared resin varnish onto a support using a die coater or the like, and then drying it to form a resin composition layer.

[0538] Examples of organic solvents include those similar to those described as components of the resin composition. Organic solvents may be used individually or in combination of two or more.

[0539] During the manufacture of the resin sheet, drying may be carried out by known methods such as heating or hot air blowing. The drying conditions are not particularly limited, but the drying should be carried out so that the content of the organic solvent in the resin composition layer is 10% by mass or less, preferably 5% by mass or less. Although it also depends on the boiling point of the organic solvent in the resin composition or resin varnish, for example, when using a resin composition or resin varnish containing 30% to 60% by mass of organic solvent, the resin composition layer can be formed by drying at 50°C to 150°C for 3 to 10 minutes.

[0540] Resin sheets can be stored by rolling them up. If the resin sheet has a protective film, it can be used after removing the protective film.

[0541] In one embodiment, the prepreg is formed by impregnating a sheet-like fibrous substrate with the resin composition of the present invention.

[0542] The sheet-like fibrous substrate used in the prepreg is not particularly limited, and commonly used prepreg substrates such as glass cloth, aramid nonwoven fabric, and liquid crystal polymer nonwoven fabric can be used. From the viewpoint of thinning printed circuit boards and semiconductor packages, the thickness of the sheet-like fibrous substrate is preferably 50 μm or less, more preferably 40 μm or less, even more preferably 30 μm or less, and even more preferably 20 μm or less. The lower limit of the thickness of the sheet-like fibrous substrate is not particularly limited and may be, for example, 10 μm or more.

[0543] Prepregs can be manufactured by known methods such as the hot melt method and the solvent method.

[0544] The thickness of the prepreg can be within the same range as the resin composition layer in the resin sheet described above.

[0545] The sheet-like laminated material of the present invention can be suitably used to form an insulating layer of a printed circuit board (for the insulating layer of a printed circuit board), and more suitably used to form an interlayer insulating layer of a printed circuit board (for the interlayer insulating layer of a printed circuit board). The sheet-like laminated material of the present invention can also be suitably used to form an insulating layer of a redistribution substrate for a semiconductor package (for the insulating layer of a redistribution substrate). In other words, the sheet-like laminated material of the present invention can be suitably used as an insulating layer for a circuit board.

[0546] [Circuit board] An insulating layer of a circuit board can be formed using the resin composition of the present invention. The present invention also provides such a circuit board, that is, a circuit board including an insulating layer made of a cured product of the resin composition of the present invention.

[0547] <Printed wiring board> In one embodiment, the circuit board of the present invention is a printed wiring board.

[0548] Printed circuit boards can be manufactured, for example, using the above-mentioned resin sheet by a method including the following steps (I) and (II). (I) A process of laminating a resin sheet onto an inner layer substrate such that the resin composition layer of the resin sheet is bonded to the inner layer substrate. (II) A step of curing (e.g., thermal curing) the resin composition layer to form an insulating layer.

[0549] -Process (I)- The "internal layer substrate" used in process (I) is a material that serves as the substrate for a printed wiring board, and examples include glass epoxy substrates, metal substrates, polyester substrates, polyimide substrates, BT resin substrates, thermosetting polyphenylene ether substrates, etc. The substrate may also have a conductive layer on one or both sides, and this conductive layer may be patterned. An internal layer substrate in which a conductive layer (circuit) is formed on one or both sides of the substrate is sometimes called an "internal layer circuit board." Furthermore, an intermediate product on which an insulating layer and / or a conductive layer is to be formed during the manufacturing of a printed wiring board is also included in the "internal layer substrate" as defined in this invention. If the printed wiring board is a circuit board with embedded components, an internal layer substrate with embedded components may be used.

[0550] Lamination of resin sheets can be performed, for example, by heating and pressing the resin sheets onto the inner layer substrate from the support side. Examples of the heating and pressing member used to heat and press the resin sheets onto the inner layer substrate (hereinafter also referred to as the "heating and pressing member") include a heated metal plate (such as a SUS end plate) or a metal roll (such as a SUS roll). The heating and pressing member may be pressed directly onto the resin sheet, or it may be pressed via an elastic material such as heat-resistant rubber so that the resin sheet can adequately follow the surface irregularities of the inner layer substrate.

[0551] The lamination of the resin sheets may be carried out by a vacuum lamination method. In the vacuum lamination method, the heat-pressing temperature is preferably in the range of 60°C to 160°C, more preferably in the range of 80°C to 140°C, the heat-pressing pressure is preferably in the range of 0.098 MPa to 1.77 MPa, more preferably in the range of 0.29 MPa to 1.47 MPa, and the heat-pressing time is preferably in the range of 20 seconds to 400 seconds, more preferably in the range of 30 seconds to 300 seconds. Lamination may preferably be carried out under reduced pressure conditions of 26.7 hPa or less.

[0552] Lamination of resin sheets can be performed using a commercially available vacuum laminator. Examples of commercially available vacuum laminators include vacuum pressure laminators manufactured by Meiki Seisakusho Co., Ltd., vacuum applicators manufactured by Nikko Materials Co., Ltd., and batch-type vacuum pressure laminators.

[0553] After lamination of the resin sheets, the laminated resin sheets may be smoothed by pressing a heat-sealing member from the support side under normal pressure (atmospheric pressure). The pressing conditions for the smoothing process can be the same as the heat-sealing conditions for lamination. The smoothing process can be performed using a commercially available laminator. Lamination and smoothing may be performed continuously using the commercially available vacuum laminator mentioned above.

[0554] The support may be removed between steps (I) and (II), or after step (II). If a metal foil is used as the support, the conductive layer may be formed using the metal foil without peeling off the support. If a metal foil with a support substrate is used as the support, the support substrate (and release layer) should be peeled off. Then, the conductive layer can be formed using the metal foil.

[0555] -Process (II)- In step (II), the resin composition layer is cured (e.g., by thermal curing) to form an insulating layer made of the cured resin composition. The curing conditions for the resin composition layer are not particularly limited, and conditions commonly used when forming an insulating layer for a printed circuit board may be used.

[0556] For example, the thermal curing conditions for the resin composition layer vary depending on the type of resin composition, but in one embodiment, the curing temperature is preferably 140°C to 250°C, more preferably 150°C to 240°C, and even more preferably 180°C to 230°C. The curing time can be preferably 5 minutes to 240 minutes, more preferably 10 minutes to 150 minutes, and even more preferably 15 minutes to 120 minutes.

[0557] Prior to thermal curing the resin composition layer, the resin composition layer may be preheated at a temperature lower than the curing temperature. For example, prior to thermal curing the resin composition layer, it may be preheated at a temperature of 50°C to 140°C, preferably 60°C to 135°C, more preferably 70°C to 130°C for 5 minutes or more, preferably 5 minutes to 150 minutes, more preferably 15 minutes to 120 minutes, and even more preferably 15 minutes to 100 minutes.

[0558] In manufacturing printed circuit boards, the following steps may be further performed: (III) drilling holes in the insulating layer, (IV) roughening the insulating layer, and (V) forming the conductor layer. These steps (III) through (V) may be carried out according to various methods known to those skilled in the art that are used in the manufacture of printed circuit boards. If the support is removed after step (II), the removal of the support may be carried out between steps (II) and (III), between steps (III) and (IV), or between steps (IV) and (V). Furthermore, if necessary, the formation of the insulating layer and the conductor layer in steps (I) through (V) may be repeated to form a multilayer circuit board.

[0559] In other embodiments, the printed circuit board of the present invention can be manufactured using the prepreg described above. The method for manufacturing a printed circuit board using a prepreg is basically the same as the method for using a resin sheet.

[0560] -Process (III)- Step (III) is a step of drilling holes in the insulating layer, thereby forming holes such as via holes and through holes in the insulating layer. Step (III) may be carried out using, for example, a drill, laser, plasma, etc., depending on the composition of the resin composition used to form the insulating layer. The dimensions and shape of the holes may be appropriately determined according to the design of the printed circuit board.

[0561] -Process (IV)- Step (IV) is a process for roughening the insulating layer. Typically, smear removal (desmear) is also performed in this step (IV). The procedure and conditions for the roughening process are not particularly limited, and known procedures and conditions commonly used when forming the insulating layer of a printed circuit board can be adopted. For example, the insulating layer can be roughened by performing swelling treatment with a swelling solution, roughening treatment with an oxidizing agent, and neutralization treatment with a neutralizing solution in this order.

[0562] The swelling solution used for the roughening treatment is not particularly limited, but examples include alkaline solutions and surfactant solutions, and is preferably an alkaline solution, with sodium hydroxide solution and potassium hydroxide solution being more preferred. Examples of commercially available swelling solutions include "Swelling Dip Securigant P" and "Swelling Dip Securigant SBU" manufactured by Atotec Japan. The swelling treatment with the swelling solution is not particularly limited, but can be carried out, for example, by immersing the insulating layer in a swelling solution at 30°C to 90°C for 1 to 20 minutes. From the viewpoint of suppressing the swelling of the resin of the insulating layer to an appropriate level, it is preferable to immerse the insulating layer in a swelling solution at 40°C to 80°C for 5 to 15 minutes.

[0563] The oxidizing agent used for the roughening treatment is not particularly limited, but examples include an alkaline permanganate solution obtained by dissolving potassium permanganate or sodium permanganate in an aqueous solution of sodium hydroxide. The roughening treatment with an oxidizing agent such as an alkaline permanganate solution is preferably carried out by immersing the insulating layer in an oxidizing agent solution heated to 60°C to 100°C for 10 to 30 minutes. Furthermore, the concentration of permanganate in the alkaline permanganate solution is preferably 5% to 10% by mass. Examples of commercially available oxidizing agents include alkaline permanganate solutions such as "Concentrate Compact CP" and "Dosing Solution Securigant P" manufactured by Attec Japan.

[0564] Furthermore, an acidic aqueous solution is preferred as the neutralizing solution used for the roughening treatment. A commercially available example is "Reduction Solution Securigant P" manufactured by Attec Japan. The treatment with the neutralizing solution can be carried out by immersing the treated surface, which has been roughened with an oxidizing agent, in a neutralizing solution at 30°C to 80°C for 5 to 30 minutes. From the standpoint of workability, etc., it is preferable to immerse the object that has been roughened with an oxidizing agent in a neutralizing solution at 40°C to 70°C for 5 to 20 minutes.

[0565] -Process (V)- Step (V) is a step of forming a conductive layer, in which a conductive layer is formed on an insulating layer. The conductive material used for the conductive layer is not particularly limited. In a preferred embodiment, the conductive layer contains one or more metals selected from the group consisting of gold, platinum, palladium, silver, copper, aluminum, cobalt, chromium, zinc, nickel, titanium, tungsten, iron, tin, and indium. The conductive layer may be a single-metal layer or an alloy layer, and examples of alloy layers include layers formed from alloys of two or more metals selected from the above group (e.g., nickel-chromium alloy, copper-nickel alloy, and copper-titanium alloy). In particular, from the viewpoint of versatility in conductor layer formation, cost, and ease of patterning, single metal layers of chromium, nickel, titanium, aluminum, zinc, gold, palladium, silver, or copper, or alloy layers of nickel-chromium alloy, copper-nickel alloy, or copper-titanium alloy are preferred, single metal layers of chromium, nickel, titanium, aluminum, zinc, gold, palladium, silver, or copper, or alloy layers of nickel-chromium alloy are more preferred, and single metal layers of copper are even more preferred.

[0566] The conductive layer may be a single-layer structure, or it may be a multi-layer structure in which two or more single-metal layers or alloy layers made of different types of metals or alloys are laminated. When the conductive layer is a multi-layer structure, the layer in contact with the insulating layer is preferably a single-metal layer of chromium, zinc, or titanium, or an alloy layer of nickel-chromium alloy.

[0567] The thickness of the conductor layer depends on the desired printed circuit board design, but is generally 3 μm to 35 μm, preferably 5 μm to 30 μm.

[0568] In one embodiment, the conductor layer may be formed by plating. From the viewpoint of easily forming fine wiring, it is preferable to form it by a semi-additive method. An example of forming the conductor layer by a semi-additive method is shown below.

[0569] First, a plating seed layer is formed on the surface of the insulating layer by electroless plating. Next, a mask pattern is formed on the formed plating seed layer, exposing a portion of the plating seed layer corresponding to the desired wiring pattern. After forming a metal layer on the exposed plating seed layer by electroplating, the mask pattern is removed. Subsequently, the unnecessary plating seed layer can be removed by etching or other means to form a conductor layer having the desired wiring pattern.

[0570] In other embodiments, the conductor layer may be formed using metal foil. When forming the conductor layer using metal foil, step (V) is preferably performed between steps (I) and (II). For example, after step (I), the support is removed and the metal foil is laminated onto the surface of the exposed resin composition layer. The lamination of the resin composition layer and the metal foil may be carried out by a vacuum lamination method. The lamination conditions may be the same as those described for step (I). Next, step (II) is performed to form an insulating layer. Subsequently, the metal foil on the insulating layer can be used to form a conductor layer having a desired wiring pattern by conventional known techniques such as the modified semi-additive method.

[0571] Metal foils can be manufactured by known methods such as electrolysis and rolling. Examples of commercially available metal foils include HLP foil and JXUT-III foil manufactured by JX Nippon Oil & Metals Corporation, and 3EC-III foil and TP-III foil manufactured by Mitsui Mining & Smelting Co., Ltd.

[0572] Alternatively, as mentioned above, if a metal foil or a metal foil with a support substrate is used as the support for the resin sheet, the conductive layer may be formed using the metal foil.

[0573] <Semiconductor package redistribution substrate> In one embodiment, the circuit board of the present invention is a redistribution substrate (redistribution layer) for a semiconductor package. The following description will be based on the manufacturing method of the semiconductor package.

[0574] The semiconductor package includes an insulating layer made of a cured product of the resin composition of the present invention as an insulating layer of the redistribution substrate. The semiconductor package may also include a sealing layer made of a cured product of the resin composition of the present invention.

[0575] A semiconductor package can be manufactured, for example, using the resin composition and resin sheet of the present invention by a method including the following steps (1) to (6). The resin composition and resin sheet of the present invention may be used to form the redistribution layer (insulating layer for forming a redistribution substrate) in step (5) or the sealing layer in step (3). An example of forming a redistribution layer and a sealing layer using the resin composition and resin sheet is shown below, but the techniques for forming redistribution layers and sealing layers of semiconductor packages are well known, and those skilled in the art can manufacture semiconductor packages using the resin composition and resin sheet of the present invention in accordance with known techniques. (1) A step of laminating a temporary fixing film onto the substrate, (2) A step of temporarily fixing the semiconductor chip onto a temporary fixing film, (3) A step of forming a sealing layer on a semiconductor chip, (4) Steps to peel off the substrate and temporary fixing film from the semiconductor chip, (5) A step of forming a rewiring layer as an insulating layer on the surface from which the substrate and temporary fixing film of the semiconductor chip have been peeled off, and (6) Step of forming a redistribution layer as a conductor layer on the redistribution formation layer.

[0576] -Process (1)- The material used for the substrate is not particularly limited. Examples of substrates include semiconductor wafers such as silicon wafers; glass wafers; glass substrates; metal substrates such as copper, titanium, stainless steel, and cold-rolled steel sheets (SPCC); substrates made by impregnating glass fibers with epoxy resin and heat-curing treatment (e.g., FR-4 substrates); and substrates made of bismaleimidotriazine resin (BT resin).

[0577] The temporary fixing film can be peeled off from the semiconductor chip in step (4) described later, and the material is not particularly limited as long as it can temporarily fix the semiconductor chip. A commercially available temporary fixing film can be used. Examples of commercially available products include Riva Alpha manufactured by Nitto Denko Corporation.

[0578] -Process (2)- Temporary fixing of semiconductor chips can be performed using known devices such as flip-chip bonders and die bonders. The layout and number of semiconductor chips can be appropriately set according to the shape and size of the temporary fixing film, the number of semiconductor packages to be produced, etc. For example, they can be temporarily fixed in a matrix arrangement with multiple rows and multiple columns.

[0579] -Process (3)- The resin composition layer of the resin sheet of the present invention is laminated onto a semiconductor chip, or the resin composition of the present invention is applied onto a semiconductor chip and cured (e.g., by heat curing) to form a sealing layer.

[0580] For example, lamination of resin sheets can be performed by removing the protective film from the resin sheet and then heat-pressing the resin sheet onto the semiconductor chip from the support side. Examples of the heat-pressing member used to heat-press the resin sheet onto the semiconductor chip (hereinafter also referred to as the "heat-pressing member") include a heated metal plate (such as a SUS end plate) or a metal roll (such as a SUS roll). It is preferable to press the heat-pressing member onto the resin sheet via an elastic material such as heat-resistant rubber, rather than pressing the resin sheet directly onto the resin sheet, so that the resin sheet can adequately follow the surface irregularities of the semiconductor chip. Lamination of the semiconductor chip and the resin sheet may also be carried out by a vacuum lamination method, and the lamination conditions are the same as those described in relation to the manufacturing method of printed circuit boards, and the preferred range is also the same.

[0581] After lamination of the resin sheets, the resin composition is heat-cured to form a sealing layer. The heat-curing conditions are the same as those described in relation to the manufacturing method of printed circuit boards.

[0582] The resin sheet support may be peeled off after the resin sheet has been laminated onto the semiconductor chip and heat-cured, or the support may be peeled off before the resin sheet has been laminated onto the semiconductor chip.

[0583] When applying the resin composition of the present invention to form a sealing layer, the application conditions are the same as those for forming the resin composition layer described in relation to the resin sheet of the present invention, and the preferred range is also the same.

[0584] -Process (4)- The method for peeling off the substrate and the temporary fixing film can be appropriately changed depending on the material of the temporary fixing film, etc. Examples include a method of peeling off the temporary fixing film by heating and foaming (or expanding) it, and a method of peeling off the temporary fixing film by irradiating it with ultraviolet light from the substrate side to reduce the adhesive strength of the temporary fixing film.

[0585] In the method of peeling off a temporary fixing film by heating and foaming (or expanding) it, the heating conditions are typically 100°C to 250°C for 1 to 90 seconds, or 5 to 15 minutes. In the method of peeling off a temporary fixing film by irradiating it with ultraviolet light from the substrate side to reduce its adhesive strength, the amount of ultraviolet light irradiated is typically 10 mJ / cm². 2 ~1000 mJ / cm 2 That is the case.

[0586] -Process (5)- The present invention provides a resin composition and resin sheet used to form a rewiring layer (an insulating layer for a rewiring substrate).

[0587] After forming the redistribution layer, via holes may be formed in the redistribution layer to interlayer connect the semiconductor chip with the conductor layer described later. The via holes may be formed by known methods depending on the material of the redistribution layer.

[0588] -Process (6)- The formation of the conductor layer on the rewiring layer may be carried out in the same manner as in step (V) described in relation to the manufacturing method of a printed circuit board. Alternatively, steps (5) and (6) may be repeated to alternately stack the conductor layer (rewiring layer) and the rewiring layer (insulating layer) (build-up).

[0589] In manufacturing a semiconductor package, the following steps may be further performed: (7) forming a solder resist layer on a conductor layer (redistribution layer), (8) forming bumps, and (9) dicing multiple semiconductor packages into individual semiconductor packages to form individual pieces. These steps may be carried out in accordance with various methods known to those skilled in the art that are used in the manufacture of semiconductor packages.

[0590] In semiconductor packages manufactured using the resin composition and resin sheet of the present invention, it is not a matter of whether the package is a fan-in type or a fan-out type package. In one embodiment, the semiconductor package of the present invention is a fan-out type package. The resin composition and resin sheet of the present invention can be applied to fan-out type panel-level packages (FOPLPs) and fan-out type wafer-level packages (FOWLPs), regardless of whether they are fan-out type panel-level packages (FOPLPs) or fan-out type wafer-level packages (FOWLPs). In one embodiment, the semiconductor package of the present invention is a fan-out type panel-level package (FOPLP) or a fan-out type wafer-level package (FOWLP).

[0591] [Semiconductor device] The semiconductor device of the present invention includes a layer made of a cured product of the resin composition of the present invention. The semiconductor device of the present invention can be manufactured using the circuit board of the present invention.

[0592] Examples of semiconductor devices include various types of semiconductor devices used in electrical products (e.g., computers, mobile phones, digital cameras, and televisions) and vehicles (e.g., motorcycles, automobiles, trains, ships, and aircraft). [Examp...

Claims

1. A resin composition comprising (A) an epoxy resin, (B) an active ester resin containing a radical polymerizable group, and (C) a resin containing an imide bond, (A) Component comprises (A-1) a liquid epoxy resin having a viscosity of 100 mPa·s or more at 25°C. Component (C) comprises at least one of (C-1) maleimide resin and (C-2) polyimide resin, A resin composition in which the total amount of component (C-1) and component (C-2) is 6% by mass or more and 20% by mass or less, relative to 100% by mass of the resin components in the resin composition.

2. The resin composition according to claim 1, wherein component (A) further comprises (A-3) an epoxy resin that is solid at 25°C.

3. The resin composition according to claim 2, wherein the content of component (A-3) is 10% by mass or more and 50% by mass or less, based on 100% by mass of the resin components in the resin composition.

4. The resin composition according to claim 2, wherein the content of component (A-3) is 25% by mass or more based on 100% by mass of the resin components in the resin composition.

5. The content of component (A-1) relative to 100% by mass of the resin component in the resin composition is M Ａ１ [As mass%], the content of component (A-3) is M Ａ３ When expressed as [mass %], the mass ratio M Ａ３ / M Ａ１ The resin composition according to claim 2, wherein the ratio is 1.5 or more and 10 or less.

6. The resin composition according to claim 1, wherein component (A-1) contains a liquid epoxy resin with an epoxy equivalent of 150 g / eq. or more.

7. The resin composition according to claim 1, wherein the content of component (A-1) is 3% by mass or more and 25% by mass or less, based on 100% by mass of the resin components in the resin composition.

8. The resin composition according to claim 1, wherein the content of component (A-1) is 15% by mass or less based on 100% by mass of the resin components in the resin composition.

9. The resin composition according to claim 1, wherein the content of component (B) is 5% by mass or more and 40% by mass or less, based on 100% by mass of the resin components in the resin composition.

10. The resin composition according to claim 1, wherein component (B) contains a monovalent group represented by the following formula (B'). 【Chemistry 1】 (In formula (B'), Ar Ｂ１ represents a divalent aromatic group which may have substituents; Ar Ｂ２ represents a monovalent aromatic group which may have substituents; * indicates a connection site.

11. The resin composition according to claim 1, wherein component (B) comprises at least one of an active ester compound represented by the following formula (B-i) and an active ester compound represented by the following formula (B-ii). 【Chemistry 2】 (In equations (B-i) and (B-ii), Ar １１ Each of these independently represents a monovalent aromatic group which may have substituents; Ar １２ Each of these independently represents a divalent aromatic group which may have substituents; R １１ each independently represents a divalent aromatic group which may have a substituent, a divalent aliphatic group which may have a substituent, an oxygen atom, a sulfur atom, or a divalent group composed of a combination thereof; Ar １１ Ar １２ , and R １１ At least one of them has a substituent containing a radical polymerizable group; m1, n1, m2, and n2 each independently represent a non-negative integer.

12. The resin composition according to claim 1, wherein component (B) contains an active ester compound having a structure represented by the following formula (B-iv-a). 【Transformation 3】 (In equation (B-iv-a), Ring Ar ４０ represents an aromatic ring which may have substituents; R ４０ This represents a monovalent group selected from a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, and an alkenyl group having 1 to 8 carbon atoms; L represents a single bond or a divalent non-aromatic group that does not contain a tetrahydrodicyclopentadiene ring.

13. (A-1) The epoxy equivalent of component is 150 g / eq. to 5,000 g / eq., The resin composition according to claim 1, wherein the active ester group equivalent of component (B) is 120 g / eq. or more and 1,000 g / eq. or less.

14. Component (C) contains component (C-1), The resin composition according to claim 1, wherein the content of component (C-1) is more than 30% by mass with respect to 100% by mass of the total amount of components (A-1) and (B).

15. Component (C) contains component (C-1), (A-1) The epoxy equivalent of component is 150 g / eq. to 5,000 g / eq., (B) The active ester group equivalent of component is 120 g / eq. or more and 1,000 g / eq. or less. The resin composition according to claim 1, wherein the maleimide group equivalent of component (C-1) is 50 g / eq. to 2,000 g / eq.

16. The resin composition according to claim 1, wherein the resin composition further comprises (D) other thermosetting resins.

17. (D) Other thermosetting resins include active ester resins that do not contain radical polymerizable groups, The resin composition according to claim 16, wherein the activated ester resin that does not contain the radical polymerizable group comprises an activated ester compound represented by the following formula (D-2). 【Chemistry 4】 (In formula (D-2), Ar ６１ Each of these independently represents a monovalent aromatic group which may have substituents; Ar ６２ Each of these independently represents a divalent aromatic group which may have substituents; R ６１ Each of these independently represents a divalent hydrocarbon group which may have substituents; Ar ６１ Ar ６２ and R ６１ None of these contain radical polymerizable groups; n ６１ (This represents a non-negative integer.)

18. The resin composition according to claim 1, further comprising (E) an inorganic filler.

19. The resin composition according to claim 18, wherein the total amount of component (C-1) and component (C-2) is 2% by mass or more and 7% by mass or less, based on 100% by mass of nonvolatile components in the resin composition.

20. The resin composition according to claim 18, wherein the content of component (E) is 65% by mass or more relative to 100% by mass of nonvolatile components in the resin composition.

21. (E) Component may include (E-1) a carbon-containing inorganic filler whose surface is treated with a surface treatment agent, or it may not include such a component. The carbon content of component (E-1) is 0.1% by mass or more relative to 100% by mass of the total amount of component (E-1). The carbon content of component (E-1) does not include the amount of carbon atoms that the surface treatment agent may contain. The resin composition according to claim 18, wherein the content of component (E-1) is less than 10% by mass relative to 100% by mass of nonvolatile components in the resin composition.

22. The resin composition according to claim 1, excluding the resin composition containing a compound represented by the following formula (B-v). 【Transformation 5】 (In equation (B-v), X ５１ This represents a divalent group containing an aromatic ring substituted with at least one alkenyl group; Z ５１ Each of these independently represents a hydrogen atom or an acyl group having a hydrocarbon group with 1 to 20 carbon atoms; At least 1 Z ５１ However, it is an acyl group having a hydrocarbon group with 1 to 20 carbon atoms.

23. The resin composition according to claim 1, excluding a resin composition containing a phenoxy resin represented by the following formula (H-1) and having a weight-average molecular weight on a polyethylene oxide basis of 10,000 to 200,000. 【Transformation 6】 (In formula (H-1), X ８１ Each of these independently represents a divalent group containing an aromatic ring substituted with at least one alkenyl group; Y ５１ Each of these independently represents a hydrogen atom, an acyl group with 2 to 21 carbon atoms, or a glycidyl group; Z ８１ Each of these independently represents a hydrogen atom or an acyl group with 2 to 21 carbon atoms, and all Z ８１ More than 5 mol% of the mixture consists of acyl groups with 2 to 21 carbon atoms; The number of carbon atoms in an acyl group includes the carbon atoms of the carbonyl group that makes up the acyl group; n ８１ (This represents a repeating number, and its average value is between 15 and 500.)

24. The resin composition according to claim 1, excluding the resin composition containing an active ester compound represented by the following formula (D-3). 【Transformation 7】 (In formula (D-3), n ７１ Each of these independently represents an integer from 0 to 6; n ７２ Each of these independently represents an integer from 1 to 5; n ７３ Each of these independently represents an integer from 1 to 6.

25. The resin composition according to claim 1, excluding the resin composition comprising an aromatic diamine compound containing an ether bond in the molecule.

26. The resin composition according to claim 1, wherein the reaction initiation temperature based on differential scanning calorimetry is 100°C or higher.

27. The reaction initiation temperature T is determined based on differential scanning calorimetry. １ (°C) is used, and the reaction peak temperature based on differential scanning calorimetry is T ２ If we consider the temperature in degrees Celsius, then the temperature difference T is... ２ -T １ The resin composition according to claim 1, wherein the temperature is 62°C or higher.

28. The process includes a step of mixing component (A), component (B), and component (C). A method for producing the resin composition according to any one of claims 1 to 27.

29. The first step involves reacting component (A-1) and component (B) to obtain a reactant having a weight-average molecular weight of 10,000 to 200,000 in terms of polyethylene oxide, The second step involves mixing the reactant obtained in the first step with component (C), A method for producing the resin composition according to claim 28, excluding a manufacturing method that includes the above.

30. A support and a resin composition layer formed on the support, A resin sheet in which the resin composition layer comprises the resin composition according to any one of claims 1 to 27.

31. A circuit board comprising a cured product of the resin composition according to any one of claims 1 to 27.

32. A semiconductor device comprising the circuit board described in claim 31.

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