Resin composition

Abstract

Provided is a resin composition which contributes to the low dielectric loss tangent of a cured product, in particular, a resin composition which contributes to the achievement of a cured product exhibiting a lower dielectric loss tangent even in a high-temperature (100 DEG C) environment. The resin composition contains (A) a cyclic ether compound having a four-membered ring or less, (B) a curing agent, (C) an inorganic filler, and (1D) an aluminum complex, and the component (A) contains (A1) a cyclic ether compound having a cationically polymerizable four-membered ring or less.

Description

Technical Field

[0001] This invention relates to resin compositions. Furthermore, it relates to resin sheets, prepregs, cured products, circuit boards, semiconductor chip packages, and semiconductor devices obtained using the resin compositions. Background Technology

[0002] In recent years, the demand for high-performance electronic devices such as smartphones and tablets has been increasing. Consequently, there is a growing demand for more functional insulating materials, such as those used in printed circuit boards and semiconductor chips, in these small electronic devices. As such sealing and insulating materials, materials formed by curing resin compositions are known; for example, the resin composition disclosed in Patent Document 1 can be cited as an example.

[0003] Existing technical documents

[0004] Patent documents

[0005] Patent Document 1: Japanese Patent Application Publication No. 2018-53092 Summary of the Invention

[0006] The problem that the invention aims to solve

[0007] In sealing and insulating materials, excellent dielectric properties (low dielectric constant, low dielectric loss tangent) are required to reduce transmission losses when operating in high-frequency environments. Here, the inventors have discovered that even cured materials with low dielectric loss tangents near room temperature (23°C) sometimes exhibit a significant increase in dielectric loss tangent at high temperatures (100°C).

[0008] The present invention was made in view of the above-mentioned problems, and aims to provide a resin composition that helps to achieve a low dielectric loss tangent in cured products, and in particular a resin composition that helps to achieve a cured product with a lower dielectric loss tangent even at high temperature (100°C).

[0009] Methods for solving problems

[0010] Through in-depth research, the inventors discovered that the above-mentioned problems can be solved and the present invention can be completed by using a resin composition having the following structure.

[0011] That is, the present invention includes the following contents.

[0012] [1] A resin composition comprising the following:

[0013] (A) Cyclic ether compounds with four or fewer members,

[0014] (B) Curing agent,

[0015] (C) Inorganic filler materials, and

[0016] (1D) aluminum complex,

[0017] (A) The component contains (A1) a cyclic ether compound with a four-membered ring or less that has cationic polymerization properties.

[0018] [2] A resin composition comprising the following:

[0019] (A) Cyclic ether compounds with four or fewer members,

[0020] (B) Curing agent,

[0021] (C) Inorganic filler materials,

[0022] (2D-1) Aluminum, and

[0023] (2D-2) Organic ligands with oxygen atoms as coordinating atoms,

[0024] (A) The component contains (A1) a cyclic ether compound with a four-membered ring or less that has cationic polymerization properties.

[0025] [3] The resin composition according to [1] or [2], wherein component (A) further comprises: a cyclic ether compound of less than four members other than component (A1) (hereinafter referred to as “component (A2)”).

[0026] [4] The resin composition according to any one of [1] to [3], wherein the content of the (A1) component is 0.1 to 6.0% by mass when the non-volatile component in the resin composition is set to 100% by mass.

[0027] [5] The resin composition according to any one of [1] to [4], wherein the content of component (C) is 50% by mass or more when the non-volatile component in the resin composition is set to 100% by mass.

[0028] [6] The resin composition according to any one of [1], [3] to [5], wherein the content of the (1D) component is 0.01 to 0.20% by mass when the non-volatile component in the resin composition is set to 100% by mass.

[0029] [7] The resin composition according to any one of [2] to [5], wherein the total content of the (2D-1) component and the (2D-2) component is 0.01 to 0.20% by mass when the non-volatile component in the resin composition is set to 100% by mass.

[0030] [8] The resin composition according to any one of [1] to [7], wherein the (A1) component comprises an alicyclic epoxy resin.

[0031] [9] The resin composition according to any one of [3] to [8], wherein component (A2) comprises an aromatic epoxy resin.

[0032]

[10] The resin composition according to any one of [1] to [9], wherein component (B) comprises an active ester curing agent.

[0033]

[11] The resin composition according to any one of [1] to

[10] , wherein component (C) comprises an inorganic oxide.

[0034]

[12] The resin composition according to any one of [1] to

[11] , wherein component (C) comprises silicon dioxide.

[0035]

[13] The resin composition according to any one of [1] to

[12] , wherein the average particle size of component (C) is 5.0 μm or less.

[0036]

[14] The resin composition according to any one of [1] to

[13] , wherein the specific surface area of ​​component (C) is 0.1 to 50 m². 2 / g.

[0037]

[15] The resin composition according to any one of [1], [3] to [6], [8] to

[14] , wherein the (1D) component comprises an aluminum chelate complex.

[0038]

[16] The resin composition according to any one of [1], [3] to [6], [8] to

[15] , wherein the (1D) component comprises: one or more aluminum complexes selected from aluminum complexes having an alkoxide as a ligand, aluminum complexes having a β-diketenolide as a ligand and aluminum complexes having a β-ketoester enolide as a ligand.

[0039]

[17] The resin composition according to any one of [2] to [5] and [7] to

[14] , wherein the (2D-1) component contains aluminum ions.

[0040]

[18] The resin composition according to any one of [2] to [5], [7] to

[14] ,

[17] , wherein the (2D-2) component comprises: one or more organic ligands selected from alcohols, alkoxides, β-diketones, β-diketone enolates, β-keto esters and β-keto ester enolates.

[0041]

[19] The resin composition according to any one of [1] to

[18] further comprises (E) free radical curable resin.

[0042]

[20] The resin composition according to any one of [1] to

[19] further contains (F) a curing accelerator.

[0043]

[21] The resin composition according to any one of [1] to

[20] further comprises (G) organic filler material.

[0044]

[22] The resin composition according to any one of [1] to

[21] further comprises (H) thermoplastic resin.

[0045]

[23] The resin composition according to any one of [1] to

[22] , wherein the dielectric loss tangent (Df) of the cured resin composition is 0.0050 or less when measured at 5.8 GHz and 100 °C.

[0046]

[24] The resin composition according to any one of [1] to

[23] is used as an insulating layer for a circuit board.

[0047]

[25] The resin composition according to any one of [1] to

[23] is used for semiconductor sealing.

[0048]

[26] A resin sheet comprising a support and a layer of the resin composition described in any one of [1] to

[25] disposed on the support.

[0049]

[27] The resin sheet according to

[26] , wherein the support is a thermoplastic resin film or a metal foil.

[0050]

[28] A prepreg, which is made by impregnating a sheet fiber substrate with any of the resin compositions described in any one of [1] to

[25] .

[0051] Cured products of the resin compositions described in any one of

[29] [1] to

[25] .

[0052]

[30] A circuit board comprising: an insulating layer of a cured resin composition having any one of [1] to

[24] .

[0053]

[31] A semiconductor chip package comprising: a sealing layer having a cured resin composition according to any one of [1] to

[23] and

[25] .

[0054]

[32] The semiconductor chip package described in

[31] is a fan-out type package.

[0055]

[33] A semiconductor device comprising the circuit board described in

[30] .

[0056]

[34] A semiconductor device comprising the semiconductor chip package described in

[31] or

[32] .

[0057] The effects of the invention

[0058] According to the present invention, a resin composition that contributes to the realization of a low dielectric loss tangent in cured products is provided, particularly a resin composition that contributes to the realization of a cured product with a lower dielectric loss tangent even at high temperature (100°C), and resin sheets, prepregs, cured products, circuit boards, semiconductor chip packages, and semiconductor devices obtained using the resin composition are also provided. Detailed Implementation

[0059] The following describes embodiments and examples in detail. However, the present invention is not limited to the embodiments and examples listed below, and can be modified as appropriate without departing from the scope of the patent claims and their equivalents.

[0060] [Explanation of terminology]

[0061] In the following explanation, the terms "above XX and below YY" and "XX to YY" indicating a numerical range, unless otherwise specified, mean a numerical range that includes both the lower and upper limits as endpoints. When numerical ranges are recorded in stages, the upper and lower limits of each numerical range can be arbitrarily combined.

[0062] In the following description, "non-volatile component" refers to the component other than the organic solvents described later in the text that constitutes the resin composition. Furthermore, "resin component" refers to the component other than the inorganic fillers described later in the text that constitutes the non-volatile component of the resin composition.

[0063] In the following explanation, unless otherwise specified, "dielectric constant" refers to "relative dielectric constant".

[0064] In the following description, unless otherwise stated, the phrase "may have substituents" when referring to a compound or group means either the case where the hydrogen atoms of the compound or group are not substituted by substituents, or the case where some or all of the hydrogen atoms of the compound or group are substituted by substituents. Furthermore, when the number of constituent atoms and carbon atoms of the compound or group are listed, unless otherwise specified, this number of constituent atoms and carbon atoms does not include the number of constituent atoms and carbon atoms containing substituents.

[0065] In the following description, "aromatic ring" refers to a ring that conforms to Hückel's rule that the number of electrons in the π-electron system of the ring is 4r+2 (r is a natural number), including monocyclic aromatic rings and fused aromatic rings consisting of two or more monocyclic aromatic rings. Unless otherwise specified, monocyclic aromatic rings are preferred as aromatic rings. Aromatic rings can be aromatic carbon rings with only carbon atoms as ring constituent atoms, or aromatic heterorings with heteroatoms such as oxygen, nitrogen, and sulfur atoms in addition to carbon atoms as ring constituent atoms. Unless otherwise specified, aromatic carbon rings are preferred as aromatic rings. Unless otherwise specified, the number of carbon atoms in an aromatic ring is preferably 3 or more, more preferably 4 or more or 5 or more, further preferably 6 or more, with an upper limit preferably 24 or less, more preferably 18 or less or 14 or less, and further preferably 10 or less. This number of carbon atoms does not include the number of substituents.

[0066] Examples of monocyclic aromatic rings include benzene rings, furan rings, thiophene rings, pyrrole rings, pyrazole rings, oxazole rings, isoxazole rings, furazine rings, thiazole rings, isothiazole rings, thiadiazole rings, imidazole rings, triazole rings, tetraazole rings, pyridine rings, pyridazine rings, pyrimidine rings, and pyridazine rings. Examples of fused aromatic rings consisting of two or more monocyclic aromatic rings include naphthyl rings, anthracene rings, phenanthrene rings, benzofuran rings, isobenzofuran rings, indole rings, isoindole rings, benzothiophene rings, benzimazole rings, indazole rings, benzooxazole rings, benzoisooxazole rings, benzothiazole rings, quinoline rings, isoquinoline rings, quinoxaline rings, acridine rings, quinazoline rings, cyclophosphine rings, phthalazine rings, pyridothiazole rings, benzotriazole rings, imidazole-pyridine rings, triazole-pyridine rings, and purine rings. Unless otherwise specified, benzene rings or naphthalene rings are preferred as aromatic rings, with benzene rings being more preferred.

[0067] In the following description, the combination of component (1D), component (2D-1), and component (2D-2) is sometimes referred to as "component (D)". Additionally, the resin composition of the first embodiment and the resin composition of the second embodiment are sometimes collectively referred to as "resin composition".

[0068] [Resin Composition of the First Embodiment]

[0069] The resin composition of the first embodiment of the present invention contains (A) a cyclic ether compound with a four-membered ring or less, (B) a curing agent, (C) an inorganic filler, and (1D) an aluminum complex. Component (A) includes (A1) a cyclic ether compound with a four-membered ring or less that has cationic polymerization properties. By incorporating components (A) to (1D) into the resin composition, a cured product exhibiting excellent dielectric loss tangent can be obtained even at high temperatures (100°C). That is, a resin composition that contributes to a low dielectric loss tangent in the cured product can be produced, and in particular, a resin composition that contributes to a lower dielectric loss tangent in the cured product even at high temperatures (100°C) can be produced. The reason for this is not clear, but it is presumed to be because: during the thermal curing of the resin composition, the cyclic ether compound with a four-membered ring or less that has cationic polymerization properties reacts with the hydroxyl groups on the surface of the inorganic filler (C) using the (1D) aluminum complex as a Lewis acid catalyst, and a cross-linking structure is also formed between the inorganic filler and the resin portion, thereby inhibiting the molecular motion of polymer molecules in the cured product. The inventors have also confirmed that the resin composition of the first embodiment of the present invention can also produce a cured product that exhibits excellent dielectric loss tangent, low coefficient of linear expansion, and high glass transition temperature even at room temperature (23°C). Regarding the resin composition of the first embodiment, component (A) may contain cyclic ether compounds with four or fewer members other than component (A1) (hereinafter referred to as "component (A2)"). Furthermore, the resin composition of the first embodiment may further contain optional components in combination with components (A) to (1D). Examples of optional components include, for example, (E) a free radical curable resin, (F) a curing accelerator, (G) an organic filler, (H) a thermoplastic resin, (I) an organic solvent, and (J) other additives. Hereinafter, each component contained in the resin composition of the first embodiment will be described in detail.

[0070] <(A) Cyclic ether compounds with four or fewer members>

[0071] The resin composition of the first embodiment of the present invention contains a cyclic ether compound with a four-membered ring or less in (A). Examples of cyclic ether compounds with a four-membered ring or less in (A) include epoxy resins as cyclic ether compounds with a three-membered ring and oxetane resins as cyclic ether compounds with a four-membered ring. Component (A) may be used alone or in combination of two or more. In one embodiment, the resin composition of the first embodiment preferably contains two or more components (A), more preferably three or more components (A), further preferably four or more components (A), and particularly preferably five or more components (A).

[0072] Regarding the content of component (A), from the viewpoint of significantly obtaining the effects of the present invention, when the non-volatile component in the resin composition is set to 100% by mass, it is preferably 1% by mass or more or 3% by mass or more, more preferably 5% by mass or more or 8% by mass or more, further preferably 10% by mass or more or 12% by mass or more, and particularly preferably 15% by mass or more or 18% by mass or more. In another embodiment, it may be 20% by mass or more, 22% by mass or more, 25% by mass or more, 27% by mass or more, etc. The upper limit is preferably 60% by mass or less or 55% by mass or less, more preferably 50% by mass or less or 45% by mass or less, further preferably 40% by mass or less, 38% by mass or less or 35% by mass or less, and particularly preferably 32% by mass or less, 30% by mass or less or 28% by mass or less.

[0073] Regarding the content of component (A), from the viewpoint of significantly obtaining the effects of the present invention, when the resin component in the resin composition is set to 100% by mass, it is preferably 5% by mass or more, 10% by mass or more, or 20% by mass or more, more preferably 25% by mass or more, 30% by mass or more, or 35% by mass or more, further preferably 40% by mass or more, 45% by mass or more, or 50% by mass or more, particularly preferably 55% by mass or more, 60% by mass or more, or 65% by mass or more. The upper limit is preferably 95% by mass or less or 90% by mass or less, more preferably 85% by mass or less or 80% by mass or less, further preferably 78% by mass or less or 75% by mass or less, particularly preferably 72% by mass or less, 70% by mass or less, or 68% by mass or less.

[0074] <(A1) Cyclic ether compounds with four or fewer members that exhibit cationic polymerization>

[0075] In the resin composition of the first embodiment of the present invention, component (A) comprises (A1) a cyclic ether compound with a four-membered ring or less that has cationic polymerization properties. Component (A1) may be used alone or in combination of two or more.

[0076] As component (A1), examples include epoxy resins with cationic polymerization properties and oxetane resins with cationic polymerization properties. Here, oxetane resins are considered component (A1) because they generally have cationic polymerization properties. Furthermore, epoxy resins are generally curable resins with an epoxy equivalent of 5000 g / eq. or less and containing epoxy groups. They are mainly classified as glycidyl-based epoxy resins and epoxy resins obtained through the direct oxidation of olefins. Here, glycidyl-based epoxy resins are considered component (A2) as described later, and epoxy resins obtained through the direct oxidation of olefins are considered component (A1).

[0077] As described above, examples of cationicly polymerizable epoxy resins in component (A1) include epoxy resins obtained through the direct oxidation of olefins. Among epoxy resins obtained through the direct oxidation of olefins, alicyclic epoxy resins are preferred, and alicyclic epoxy resins having a 6-membered ring are more preferred. That is, component (A1) preferably includes a cationicly polymerizable epoxy resin, more preferably an epoxy resin obtained through the direct oxidation of olefins, further preferably an alicyclic epoxy resin, and particularly preferably an alicyclic epoxy resin having a 6-membered ring. The cationicly polymerizable epoxy resin typically has 1 or more epoxy groups in its molecule, preferably 2 or more.

[0078] The number of carbon atoms in a cationicly polymerizable epoxy resin is preferably 2 to 100. The lower limit of the number of carbon atoms in a cationicly polymerizable epoxy resin, as described above, is preferably 2 or more, more preferably 3 or more, 4 or more, or 5 or more, further preferably 6 or more, or 7 or more, and particularly preferably 8 or more, or 9 or more. The upper limit of the number of carbon atoms in a cationicly polymerizable epoxy resin, as described above, is preferably 100 or less, more preferably 90 or less, 80 or less, or 70 or less, further preferably 60 or less, or 50 or less, and particularly preferably 40 or less, or 30 or less. Additionally, in one embodiment, it may be 25 or less, 20 or less, 15 or less, etc.

[0079] The molecular weight of the cationic polymerizable epoxy resin is preferably 50 to 5000. The lower limit of the molecular weight of the cationic polymerizable epoxy resin, as described above, is preferably 50 or more, more preferably 80 or more, further preferably 100 or more or 120 or more, and particularly preferably 140 or more or 160 or more. The upper limit of the molecular weight of the cationic polymerizable epoxy resin, as described above, is preferably 5000 or less, more preferably 4000 or less, 3000 or less, or 2000 or less, further preferably 1000 or less or 800 or less, and particularly preferably 600 or less or 500 or less. In one embodiment, it may be 450 or less, 400 or less, 350 or less, 300 or less, etc.

[0080] In one embodiment, the cationicly polymerizable epoxy resin preferably has a partial structure represented by formula (A-1) or a partial structure represented by formula (A-2). The cationicly polymerizable epoxy resin may have both the partial structure represented by formula (A-1) and the partial structure represented by formula (A-2). Furthermore, in the case of having both the partial structure represented by formula (A-1) and the partial structure represented by formula (A-2), the cyclohexane ring in formula (A-1) and the cyclohexane ring in formula (A-2) may be shared.

[0081]

Chemistry 1

[0082]

[0083] (In equations (A-1) and (A-2), R) a1 Indicates an alkyl group having 1 to 6 hydrogen atoms or carbon atoms. * Indicates a bonding end with other parts of the epoxy resin structure. a1 Representing integers from 0 to 11 means that the connection point with other parts of the structure is n. a1 n a2 Representing integers from 0 to 11 means that the connection point with other parts of the structure is n. a2 indivual.)

[0084] In equation (A-1), R a1 This refers to an alkyl group having 1 to 6 hydrogen atoms or carbon atoms. The alkyl group is a chain (straight-chain or branched) alkyl group or a cyclic alkyl group. The alkyl group preferably has 1 to 5 carbon atoms, more preferably 1 to 3, and even more preferably 1. Examples of chain alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, hexyl, 2-ethylhexyl, octyl, decyl, etc., with methyl, ethyl, n-propyl, or isopropyl being preferred, more preferably methyl or ethyl, and even more preferably methyl. Additionally, examples of cyclic alkyl groups include cyclopentyl, cyclohexyl, cyclooctyl, etc. Among these, R... a1 Preferably, hydrogen atoms or methyl groups are used.

[0085] In equation (A-1), n a1 Represents integers from 0 to 11. a1 The lower limit is preferably 1 or more, and more preferably 2 or more. a1 The upper limit is preferably 10 or less or 8, more preferably 6 or less or 5, and even more preferably 4 or less or 3.

[0086] In equation (A-2), n a1 Represents integers from 0 to 10. a1 The lower limit is preferably 1 or more, and more preferably 2 or more. a1 The upper limit is preferably 8 or less or 7, more preferably 6 or less or 5, and even more preferably 4 or less or 3.

[0087] Specific examples of epoxy resins with cationic polymerization properties include epoxy resins represented by the following formulas (A-3-1) to (A-3-12), preferably epoxy resins represented by formula (A-3-1), epoxy resins represented by formula (A-3-2), or epoxy resins represented by formula (A-3-3), and more preferably epoxy resins represented by formula (A-3-1).

[0088]

Chemistry 2

[0089]

[0090] (In the formula, m, n, n1, n2, and n3 each independently represent integers greater than or equal to 0.)

[0091] Commercially available epoxy resins with cationic polymerization properties include, for example, Cargill's "Limonene dioxide" (an epoxy resin represented by formula (A-3-1)); Daicel's "Cerokide 2021P" (an epoxy resin represented by formula (A-3-2)), "EHPE3150" (an epoxy resin represented by formula (A-3-3)), "Cerokide 2081" (an epoxy resin represented by formula (A-3-4)), "EPOLEAD PB4700", "EPOLEAD PB3600", "EPOLEAD AT501" (an epoxy resin represented by formula (A-3-6)), and "EPOLEAD..." GT401 (an epoxy resin represented by formula (A-3-7)), Cyclomar M100 (an epoxy resin represented by formula (A-3-8)), and Cycloki Said 2000 (an epoxy resin represented by formula (A-3-9)); DE-102 (an epoxy resin represented by formula (A-3-11)), DE-103 (an epoxy resin represented by formula (A-3-11)), and THI-DE (an epoxy resin represented by formula (A-3-12)) manufactured by ENEOS; DCPD-DE (an epoxy resin represented by formula (A-3-10)) manufactured by Nippon Materials Technology Co., Ltd.; and LDO (an epoxy resin represented by formula (A-3-1)) manufactured by SYMRISE, etc.

[0092] (A1) The number of oxetane rings in one molecule of the oxetane resin is usually one or more, preferably two or more, and may be two. In addition, one type of oxetane resin may be used alone, or two or more types may be used in combination.

[0093] The number of carbon atoms in the oxetane resin is preferably 3 to 100. The lower limit of the number of carbon atoms in the oxetane resin, as described above, is preferably 3 or more, more preferably 4 or more, 5 or more, or 6 or more, further preferably 7 or more, or 8 or more, and particularly preferably 9 or more, 10 or more, or 11 or more. The upper limit of the number of carbon atoms in the oxetane resin, as described above, is preferably 100 or less, more preferably 80 or less, 50 or less, 45 or less, 40 or less, or 35 or less, further preferably 30 or less, 25 or less, or 20 or less, and particularly preferably 18 or less, 16 or less, or 14 or less.

[0094] The molecular weight of the oxetane resin is preferably between 100 and 1000. The lower limit of the molecular weight of the oxetane resin, as described above, is preferably 100 or more, more preferably 120 or more or 140 or more, further preferably 160 or more or 180 or more, and particularly preferably 200 or more or 210 or more. The upper limit of the molecular weight of the oxetane resin, as described above, is preferably 1000 or less, more preferably 800 or less, 600 or less, 500 or less or 400 or less, further preferably 350 or less, 300 or less or 280 or less, and particularly preferably 260 or less, 240 or less or 220 or less.

[0095] The oxetane resin is preferably a liquid at 20°C. The viscosity of the oxetane resin at 20°C is preferably 0.1 mPa·s or more, more preferably 1 mPa·s or more, even more preferably 7 mPa·s or more, preferably 100 mPa·s or less, more preferably 25 mPa·s or less, and even more preferably 16 mPa·s or less. The viscosity can be measured using an E-type viscometer (e.g., Toki Sangyo Co., Ltd. "RE-80U", 1°34'×R24 cone).

[0096] Oxycyclic butane resins preferably contain aliphatic groups. Oxycyclic butane resins containing aliphatic groups are also referred to as "aliphatic oxycyclic butane resins." The aliphatic groups contained in the oxycyclic butane resin can be linear, branched, or cyclic, preferably linear or branched, and more preferably linear. Furthermore, the aliphatic groups can be saturated or unsaturated, preferably saturated. For example, the oxycyclic butane resin may contain monovalent or divalent or more aliphatic groups. The number of carbon atoms in this aliphatic group is typically 1 or more, preferably 2 or more, more preferably 8 or less, more preferably 6 or less, and even more preferably 4 or less. Preferred examples of such aliphatic groups include chain hydrocarbon groups with monovalent or divalent or more. Specific examples of these chain hydrocarbon groups include alkyl groups such as methyl, ethyl, propyl, and butyl; and alkylene groups such as methylene, ethylene, propylene, and butylene.

[0097] Examples of oxetane resins include those represented by formulas (A-4-1) to (A-4-8), with those represented by formula (A-4-3) being preferred.

[0098]

Transformation 3

[0099]

[0100] Commercially available products can be used as oxetane resins. Examples of commercially available oxetane resins include: ARON OXETANE series from Toa Synthetic Co., Ltd., namely “OXT-101” (resin of formula (A-4-1), “OXT-212” (resin of formula (A-4-2), “OXT-221” (resin of formula (A-4-3), and “OXT-121” (resin of formula (A-4-6)); and ETERNACOLL series from UBE Co., Ltd., namely “EHO” (resin of formula (A-4-1), “HBOX” (resin of formula (A-4-4), “OXMA” (resin of formula (A-4-5), “OXBP” (resin of formula (A-4-8), and “OXIPA” (resin of formula (A-4-7)).

[0101] The functional group equivalent of component (A1) is preferably 50 g / eq. to 3000 g / eq. The lower limit of the functional group equivalent of component (A1) is as described above, preferably 50 g / eq. or more, more preferably 60 g / eq. or more or 70 g / eq. or more, further preferably 80 g / eq. or more, and particularly preferably 90 g / eq. or more. The upper limit of the functional group equivalent of component (A1) is as described above, preferably 3000 g / eq. or less, more preferably 2000 g / eq. or less or 1000 g / eq. or less, further preferably 800 g / eq. or less or 500 g / eq. or less, and particularly preferably 300 g / eq. or less or 200 g / eq. or less. The functional group equivalent of component (A1) is the mass of component (A1) per 1 equivalent of functional group (epoxy or oxetyl).

[0102] Regarding the content of component (A1), when the non-volatile component in the resin composition is set to 100% by mass, from the viewpoint of significantly obtaining the effects of the present invention, it is preferably 0.01% by mass or more or 0.02% by mass or more, more preferably 0.05% by mass or more or 0.08% by mass or more, further preferably 0.1% by mass or more or 0.2% by mass or more, particularly preferably 0.5% by mass or more, 0.8% by mass or more, or 0.9% by mass or more. Regarding the upper limit, from the viewpoint of reducing the coefficient of linear expansion of the cured product and increasing the glass transition temperature of the cured product, it is preferably 20.0% by mass or less or 15.0% by mass or less, more preferably 10.0% by mass or less, 8.0% by mass or less, or 6.0% by mass or less, and further preferably 5.0% by mass or less. In one embodiment, it may be 4.0% by mass or less, 3.0% by mass or less, 2.0% by mass or less, 1.5% by mass or less, 1.2% by mass or less, etc. In one embodiment, regarding the content of component (A1), when the non-volatile component in the resin composition is set to 100% by mass, it is preferably 0.1 to 6.0% by mass.

[0103] Regarding the content of component (A1), when the resin component in the resin composition is set to 100% by mass, from the viewpoint of significantly obtaining the effects of the present invention, it is preferably 0.05% by mass or more, 0.08% by mass or more, or 0.1% by mass or more, more preferably 0.2% by mass or more, 0.5% by mass or more, or 0.8% by mass or more, further preferably 1.0% by mass or more, 1.2% by mass or more, or 1.5% by mass or more, and particularly preferably 1.8% by mass or more, 2.0% by mass or more, or 2.2% by mass or more. Regarding the upper limit, from the viewpoint of reducing the coefficient of linear expansion of the cured product and increasing the glass transition temperature of the cured product, it is preferably 40% by mass or less, more preferably 35% by mass or less, or 30% by mass or less, further preferably 25% by mass or less, or 20% by mass or less, and particularly preferably 15% by mass or less, or 12% by mass or less. Additionally, in one embodiment, it may be 10% by mass or less, 8% by mass or less, 6% by mass or less, 4% by mass or less, 3% by mass or less, or 2.5% by mass or less, etc.

[0104] Regarding the content of component (A1), from the viewpoint of significantly obtaining the effects of the present invention, when component (A) in the resin composition is set to 100% by mass, it is preferably 0.1% by mass or more or 0.2% by mass or more, more preferably 0.5% by mass or more, 0.8% by mass or more or 1.0% by mass or more, further preferably 1.5% by mass or more, 2.0% by mass or more or 2.5% by mass or more, and particularly preferably 3.0% by mass or more, 3.2% by mass or more or 3.4% by mass or more. There is no particular limitation on the upper limit, and it can be 100% by mass, or it can be 90% by mass or less, 70% by mass or less, 50% by mass or less, 40% by mass or less, 30% by mass or less, 20% by mass or less, 15% by mass or less, 10% by mass or less, 8% by mass or less, 5% by mass or less, 4% by mass or less, etc.

[0105] <Cyclic ether compounds with a ring smaller than four members other than (A1)>

[0106] In the resin composition of the first embodiment of the present invention, component (A) may include cyclic ether compounds with a four-membered ring or less other than component ((A2) component), preferably including component (A2). Component (A2) may be used alone or in combination of two or more. In one embodiment, the resin composition of the first embodiment preferably contains two or more (A2) components, more preferably three or more (A2) components, and even more preferably four or more (A2) components.

[0107] As component (A2), examples include glycidyl-based epoxy resins, with glycidyl-based epoxy resins having aromatic rings being preferred (hereinafter also referred to as "aromatic epoxy resins"). More specifically, as component (A2), examples include, for instance, bixylenol-type epoxy resins, bisphenol A-type epoxy resins, bisphenol F-type epoxy resins, bisphenol S-type epoxy resins, bisphenol AF-type epoxy resins, dicyclopentadiene-type epoxy resins, triphenol-type epoxy resins, naphthol phenolic varnish-type epoxy resins, phenol phenolic varnish-type epoxy resins, tert-butylcatechol-type epoxy resins, naphthalene-type epoxy resins, naphthol-type epoxy resins, anthracene-type epoxy resins, glycidylamine-type epoxy resins, glycidyl ester-type epoxy resins, cresol phenolic varnish-type epoxy resins, and phenolic aromatic... Alkyl epoxy resins, biphenyl epoxy resins, biphenyl aralkyl epoxy resins, linear aliphatic epoxy resins, epoxy resins with butadiene structures, heterocyclic epoxy resins, epoxy resins containing spirocyclic rings, cyclohexane epoxy resins, cyclohexane-diethanol epoxy resins, naphthalene ether epoxy resins, tris(hydroxymethyl) epoxy resins, tetraphenylethane epoxy resins, isocyanurate epoxy resins, phenol-benzylmethyllactam epoxy resins, glycerol epoxy resins, epoxy resins containing alkoxy groups, epoxy resins containing fluorene structures, halogenated epoxy resins, etc. (A2) The component preferably includes an aromatic epoxy resin, more preferably it includes one or more epoxy resins selected from bisphenol A type epoxy resin, naphthyl type epoxy resin, biphenyl type epoxy resin, bixylenol type epoxy resin, naphthyl ether type epoxy resin and dicyclopentadiene type epoxy resin, further preferably it includes one or more epoxy resins selected from bisphenol A type epoxy resin, naphthyl type epoxy resin and biphenyl type epoxy resin, even more preferably it includes one or more epoxy resins selected from naphthyl type epoxy resin and biphenyl type epoxy resin, and particularly preferably it includes naphthyl type epoxy resin and biphenyl type epoxy resin.

[0108] In one embodiment, regarding the (A2) component, from the viewpoint of significantly obtaining the effects of the present invention, it is preferable to include two or more epoxy resins selected from bisphenol A type epoxy resin, naphthalene type epoxy resin, biphenyl type epoxy resin, bixylenol type epoxy resin, naphthalene ether type epoxy resin and dicyclopentadiene type epoxy resin; more preferably, it includes three or more epoxy resins selected from the above group; and even more preferably, it includes four or more epoxy resins selected from the above group.

[0109] In one embodiment, from the viewpoint of reducing the coefficient of linear expansion of the cured product, component (A2) preferably includes one or more epoxy resins selected from bisphenol A type epoxy resin, bixylenol type epoxy resin, naphthalene ether type epoxy resin and dicyclopentadiene type epoxy resin, more preferably includes two or more epoxy resins selected from the above group, further preferably includes three or more epoxy resins selected from the above group, and particularly preferably includes four or more epoxy resins selected from the above group.

[0110] The resin composition of the present invention preferably includes an epoxy resin having two or more epoxy groups in one molecule as component (A2). From the viewpoint of significantly obtaining the desired effects of the present invention, the proportion of epoxy resin having two or more epoxy groups in one molecule is preferably 50% by mass or more, more preferably 60% by mass or more, and particularly preferably 70% by mass or more, relative to 100% by mass of component (A2).

[0111] Epoxy resins include those that are liquid at 20°C (hereinafter sometimes referred to as "liquid epoxy resin") and those that are solid at 20°C (hereinafter sometimes referred to as "solid epoxy resin"). Regarding the resin composition of the present invention, as component (A2), it may contain only liquid epoxy resin, only solid epoxy resin, or a combination of both. In one embodiment, the resin composition of the first embodiment of the present invention preferably contains a combination of liquid epoxy resin and solid epoxy resin as component (A2).

[0112] As a liquid epoxy resin, a liquid epoxy resin having two or more epoxy groups in one molecule is preferred.

[0113] Examples of liquid epoxy resins include, for example, glycerol-type epoxy resins, bisphenol A-type epoxy resins, bisphenol F-type epoxy resins, bisphenol AF-type epoxy resins, naphthalene-type epoxy resins, glycidyl ester-type epoxy resins, glycidylamine-type epoxy resins, phenolic varnish-type epoxy resins, cyclohexanediol-type epoxy resins, cyclic aliphatic glycidyl ethers, epoxy resins having a butadiene structure, dicyclopentadiene-type epoxy resins, epoxy resins containing an alkoxy group backbone, and epoxy resins containing a fluorene structure, with bisphenol A-type epoxy resins being preferred.

[0114] Specific examples of liquid epoxy resins include Nagasek Metex's "EX-992L", Mitsubishi Chemical's "YX7400", DIC's "HP4032", "HP4032D", and "HP4032SS" (naphthalene-type epoxy resin); Mitsubishi Chemical's "828US", "jER828EL", "828EL", "825", "Epicoet 828EL", DIC's "850S" (bisphenol A type epoxy resin); and Mitsubishi Chemical's "jER..." 807, 1750 (bisphenol F type epoxy resin); JER152 (phenolic varnish type epoxy resin) manufactured by Mitsubishi Chemical Corporation; 630, 630LSD, 604 (glycidylamine type epoxy resin) manufactured by Mitsubishi Chemical Corporation; ED-523T (glycerol type epoxy resin) manufactured by ADEKA Corporation; EP-3950L, EP-3980S (glycidylamine type epoxy resin) manufactured by ADEKA Corporation; EP-4088S, EP-4088L (EP-4088 type epoxy resin) manufactured by ADEKA Corporation. "(Dicyclopentadiene type epoxy resin); ZX-1059 (a mixture of bisphenol A type epoxy resin and bisphenol F type epoxy resin) manufactured by Nippon Steel Kemica & Matterol Co., Ltd.; EX-721 (glycidyl ester type epoxy resin) manufactured by Nagasek Metex Co., Ltd.; EX-991L (an epoxy resin containing an alkoxy backbone) manufactured by Nagasek Metex Co., Ltd.; PB-3600 manufactured by Daicel Co., Ltd.; JP-100 and JP-200 (epoxy resins with butadiene structure) manufactured by Nippon Soda Co., Ltd. The following epoxy resins are used: "ZX1658" and "ZX1658GS" (liquid 1,4-glycidylcyclohexane type epoxy resin) manufactured by Nippon Steel Kemical & Materia; "EG-280" (fluorene-containing epoxy resin) manufactured by Osaka Gas Chemical Co., Ltd.; "EX-201", "EX-321L", "EX-212L", "EX-214L", "EX-810P", "EX-991L", and "EX-121" manufactured by Nagasek Technologies Co., Ltd.; and "Shouferry CDMDG" manufactured by Resonack Co., Ltd. These can be used individually or in combination of two or more.

[0115] As a solid epoxy resin, a solid epoxy resin having two or more epoxy groups in one molecule is preferred, and an aromatic solid epoxy resin having three or more epoxy groups in one molecule is more preferred.

[0116] Examples of solid epoxy resins include xylenol-type epoxy resins, naphthalene-type epoxy resins, naphthalene-type tetrafunctional epoxy resins, naphthol phenolic varnish-type epoxy resins, cresol phenolic varnish-type epoxy resins, dicyclopentadiene-type epoxy resins, triphenol-type epoxy resins, naphthol-type epoxy resins, biphenyl-type epoxy resins, biphenyl aralkyl-type epoxy resins, naphthyl ether-type epoxy resins, anthracene-type epoxy resins, bisphenol A-type epoxy resins, bisphenol AF-type epoxy resins, phenol aralkyl-type epoxy resins, tetraphenylethane-type epoxy resins, phenol benzylformamide-type epoxy resins, and epoxy resins containing fluorene structures. Preferably, naphthalene-type epoxy resins, biphenyl-type epoxy resins, xylenol-type epoxy resins, naphthyl ether-type epoxy resins, or dicyclopentadiene-type epoxy resins are preferred, and naphthalene-type epoxy resins or biphenyl-type epoxy resins are more preferred.

[0117] Specific examples of solid epoxy resins include, for instance, DIC's "HP-4032H" and "HP-4032SS" (naphthalene-type epoxy resin); DIC's "HP-4700" and "HP-4710" (naphthalene-type tetrafunctional epoxy resin); DIC's "N-690" and "N-695" (cresol phenolic varnish type epoxy resin); DIC's "HP-7200," "HP-7200HH," "HP-7200H," and "HP-7200L" (dicyclopentadiene type epoxy resin); and DIC's "EXA-7311" and "E..." XA-7311-G3, EXA-7311-G4, EXA-7311-G4S, HP-6000, HP-6000L (naphthalene ether type epoxy resin); EPPN-502H (triphenol type epoxy resin) manufactured by Nippon Kayaku Co., Ltd.; NC7000L (naphthalene phenolic varnish type epoxy resin) manufactured by Nippon Kayaku Co., Ltd.; NC3000, NC3000L, NC3000FH, NC3100 (biphenyl type epoxy resin) manufactured by Nippon Kayaku Co., Ltd.; NC3000H (biphenyl aralkyl type epoxy resin) manufactured by Nippon Kayaku Co., Ltd. The following epoxy resins are manufactured by Nippon Steel Kemical & Materia: "ESN475V" and "ESN4100V" (naphthalene-type epoxy resin); "ESN485" (naphthol-type epoxy resin); "ESN375" (dihydroxynaphthalene-type epoxy resin); "YX4000H," "YX4000," "YX4000HK," and "YL7890" (bi-xylenol-type epoxy resin); "YL6121" (biphenyl-type epoxy resin); and "YX8800" (a type of epoxy resin). Anthracene-type epoxy resin; Mitsubishi Chemical's "YX7700" (phenolic aralkyl type epoxy resin); Osaka Gas Chemical's "PG-100" and "CG-500"; Mitsubishi Chemical's "YL7760" (bisphenol AF type epoxy resin); Mitsubishi Chemical's "YL7800" (fluorene-containing epoxy resin); Mitsubishi Chemical's "jER1010" (bisphenol A type epoxy resin); Mitsubishi Chemical's "jER1031S" (tetraphenylethane type epoxy resin); Nippon Kayaku Co., Ltd.'s "WHR991S" (phenolic benzylformamide type epoxy resin), etc. These can be used individually or in combination.

[0118] The epoxy equivalent of component (A2) is preferably 50 to 5000 g / eq. The lower limit of the epoxy equivalent, as described above, is preferably 50 g / eq. or more, more preferably 60 g / eq. or more, further preferably 80 g / eq. or more, and particularly preferably 110 g / eq. or more. The upper limit of the epoxy equivalent, as described above, is preferably 5000 g / eq. or less, more preferably 3000 g / eq. or less or 2000 g / eq. or less, further preferably 1000 g / eq. or less, and particularly preferably 500 g / eq. or less. The epoxy equivalent is the mass of epoxy resin containing 1 equivalent of epoxy groups, and can be determined according to JIS K7236.

[0119] The weight-average molecular weight (Mw) of component (A2) is preferably 100 to 5000, more preferably 250 to 3000, and even more preferably 400 to 1500. The weight-average molecular weight (Mw) of the epoxy resin can be determined by using the GPC method as a value converted from polystyrene.

[0120] When the resin composition of the first embodiment contains component (A2), regarding the content of component (A2), from the viewpoint of significantly obtaining the effects of the present invention, when the non-volatile component in the resin composition is set to 100% by mass, it is preferably 1% by mass or more, more preferably 3% by mass or more or 5% by mass or more, further preferably 8% by mass or more or 10% by mass or more, and particularly preferably 12% by mass or more or 15% by mass or more. In another embodiment, it may be 18% by mass or more, 20% by mass or more, 22% by mass or more, 25% by mass or more, etc. The upper limit is preferably 60% by mass or less or 55% by mass or less, more preferably 50% by mass or less or 45% by mass or less, further preferably 40% by mass or less or 35% by mass or less, and particularly preferably 30% by mass or less or 28% by mass or less.

[0121] When the resin composition of the first embodiment contains component (A2), regarding the content of component (A2), when the resin component in the resin composition is set to 100% by mass, it is preferably 5% by mass or more or 10% by mass or more, more preferably 15% by mass or more or 20% by mass or more, further preferably 25% by mass or more or 30% by mass or more, and particularly preferably 35% by mass or more, 40% by mass or more, or 45% by mass or more. In another embodiment, it may be 50% by mass or more, 55% by mass or more, 60% by mass or more, 62% by mass or more, etc. The upper limit is preferably 95% by mass or less or 90% by mass or less, more preferably 85% by mass or less or 80% by mass or less, further preferably 78% by mass or less, 75% by mass or less, or 72% by mass or less, and particularly preferably 70% by mass or less, 68% by mass or less, or 65% by mass or less.

[0122] When the resin composition of the first embodiment contains component (A2), regarding the content of component (A2), from the viewpoint of significantly obtaining the effects of the present invention, when component (A) in the resin composition is set to 100% by mass, it is preferably 99.9% by mass or less or 99.8% by mass or less, more preferably 99.5% by mass or less, 99.2% by mass or less or 99.0% by mass or less, further preferably 98.5% by mass or less, 98.0% by mass or less or 97.5% by mass or less, and particularly preferably 97.0% by mass or less, 96.8% by mass or less or 96.6% by mass or less. There is no particular limitation on the lower limit, which can be 0% by mass, 10% by mass or more, 30% by mass or more, 50% by mass or more, 60% by mass or more, 70% by mass or more, 80% by mass or more, 85% by mass or more, 90% by mass or more, 92% by mass or more, 95% by mass or more, 96% by mass or more, etc.

[0123] When the resin composition of the first embodiment contains component (A2), from the viewpoint of significantly obtaining the effects of the present invention, the mass ratio of component (A1) to component (A2) [(A1) component / (A2) component] is preferably 0.0001 or more or 0.0005 or more, more preferably 0.001 or more or 0.002 or more, further preferably 0.005 or more or 0.008 or more, and particularly preferably 0.01 or more, 0.02 or more, or 0.03 or more. There is no particular limitation on the upper limit, but from the viewpoint of reducing the coefficient of linear expansion of the cured product and increasing the glass transition temperature of the cured product, it is preferably 10 or less, more preferably 5 or less or 2 or less, further preferably 1 or less or 0.8 or less, and particularly preferably 0.5 or less, 0.4 or less, or 0.3 or less. In another embodiment, it may be 0.2 or less, 0.1 or less, 0.08 or less, 0.05 or less, 0.04 or less, etc.

[0124] <(B) Curing Agent>

[0125] The resin composition of the first embodiment of the present invention contains a curing agent (B). The curing agent (B) has the function of reacting with a cyclic ether compound of four members or less in (A) to cure the resin composition. The curing agent (B) can be used alone or in combination of two or more. In one embodiment, the curing agent (B) preferably includes an epoxy resin curing agent, and the curing agent (B) is more preferably an epoxy resin curing agent.

[0126] (B) The functional group equivalent of the curing agent is preferably 50 g / eq. to 3000 g / eq., more preferably 100 g / eq. to 1000 g / eq., even more preferably 100 g / eq. to 500 g / eq., and particularly preferably 100 g / eq. to 300 g / eq. The functional group equivalent is the mass of (B) curing agent per 1 equivalent of functional group.

[0127] Examples of curing agents (B) include reactive ester-based curing agents, carbodiimide-based curing agents, phenolic curing agents, acid anhydride-based curing agents, amine-based curing agents, benzoxazine-based curing agents, cyanate ester-based curing agents, and thiol-based curing agents. From the viewpoint of significantly achieving the effects of the present invention, it is preferable that the curing agent (B) comprises one or more selected from phenolic curing agents, reactive ester-based curing agents, and carbodiimide-based curing agents; more preferably, it comprises one or more selected from reactive ester-based curing agents and carbodiimide-based curing agents; and even more preferably, it comprises an reactive ester-based curing agent. In one embodiment, the curing agent (B) preferably comprises two or more selected from phenolic curing agents, reactive ester-based curing agents, and carbodiimide-based curing agents; more preferably, it comprises a phenolic curing agent, a reactive ester-based curing agent, and a carbodiimide-based curing agent.

[0128] There are no particular limitations on the active ester-based curing agent; compounds having one or more active ester groups per molecule can be used. Among these, compounds having two or more highly reactive ester groups per molecule, such as phenolic esters, thiophenolic esters, N-hydroxyamine esters, and heterocyclic hydroxyl esters, are preferred as active ester-based curing agents. This active ester compound is preferably obtained through a condensation reaction of a carboxylic acid compound and / or a thiocarboxylic acid compound with a hydroxyl compound and / or a thiol compound. Particularly from the viewpoint of improved heat resistance, active ester compounds obtained from carboxylic acid compounds and hydroxyl compounds are preferred, and active ester compounds obtained from carboxylic acid compounds and phenol compounds and / or naphthol compounds are more preferred. In one embodiment, the active ester compound may be an active ester compound obtained from a carboxylic acid compound and a phenol compound or a naphthol compound, or an active ester compound obtained from a carboxylic acid compound and a phenol compound and a naphthol compound.

[0129] Examples of carboxylic acid compounds include, for example, benzoic acid, acetic acid, succinic acid, maleic acid, itaconic acid, phthalic acid, isophthalic acid, terephthalic acid, and pyromellitic acid.

[0130] Examples of phenolic and / or naphthol compounds include, for example, hydroquinone, resorcinol, bisphenol A, bisphenol F, bisphenol S, phenolnaphthalene, methylated bisphenol A, methylated bisphenol F, methylated bisphenol S, phenol, o-cresol, m-cresol, p-cresol, catechol, α-naphthol, β-naphthol, and 1,5-dihydroxyphenol. Naphthalene, 1,6-dihydroxynaphthalene, 2,6-dihydroxynaphthalene, dihydroxybenzophenone, trihydroxybenzophenone, tetrahydroxybenzophenone, phloroglucinol, phenyl phenoxide, dicyclopentadiene-type diphenol compounds, phenolic varnish, etc. Among these, "dicyclopentadiene-type diphenol compounds" refer to diphenol compounds obtained by the condensation of two phenol molecules into one molecule of dicyclopentadiene.

[0131] Specifically, as an active ester-based curing agent, a dicyclopentadiene-type active ester-based curing agent, a naphthalene-type active ester-based curing agent containing a naphthalene structure, an active ester-based curing agent containing an acetylated form of phenolic varnish, and an active ester-based curing agent containing a benzoyl form of phenolic varnish are preferred. More preferably, at least one selected from dicyclopentadiene-type active ester-based curing agents and naphthalene-type active ester-based curing agents is preferred, and a naphthalene-type active ester-based curing agent is even more preferred. As a dicyclopentadiene-type active ester-based curing agent, an active ester-based curing agent containing a dicyclopentadiene-type diphenol structure is preferred.

[0132] Commercially available reactive ester curing agents, including those containing a dicyclopentadiene-type diphenol structure, include "EXB9451", "EXB9460", "EXB9460S", "HPC-8000L-65TM", "HPC-8000-65T", "EXB-8000H", and "EXB-8000L-65TM" (manufactured by DIC); and those containing a naphthalene structure, include "EXB-9416-70BK", "EXB-8100L-65T", "HPC-8150-62T", "EXB-8150L-65T", "EXB-8100L-65T", and "EXB-8" (D...). (Manufactured by IC Corporation); as a phosphorus-containing reactive ester curing agent, "EXB9401" (manufactured by DIC Corporation) can be listed; as a reactive ester curing agent containing acetylated phenolic varnishes, "DC808" (manufactured by Mitsubishi Chemical Corporation) can be listed; as a reactive ester curing agent containing benzoyl compounds in phenolic varnishes, "YLH1026", "YLH1030", "YLH1048" (manufactured by Mitsubishi Chemical Corporation) and "EXB-8500-65T" (manufactured by DIC Corporation) can be listed; as a reactive ester curing agent containing styrene and naphthalene structures, "PC1300-02-65T" and "PC1300-02-65MA" (manufactured by Air Weather Corporation) can be listed, etc.

[0133] Carbodiimide-based curing agents are compounds having one or more carbodiimide groups (-N=C=N-) in one molecule, and preferably compounds having two or more carbodiimide groups in one molecule. Examples of carbodiimide-based curing agents include, for example, aliphatic dicarbodiimides such as tetramethylenebis(tert-butylcarbodiimide) and cyclohexanebis(methylene-tert-butylcarbodiimide); aromatic dicarbodiimides such as phenylene-bis(xylylcarbodiimide); aliphatic polycarbodiimides such as polyhexamethylenecarbodiimide, polytrimethylhexamethylenecarbodiimide, polycyclohexylcarbodiimide, poly(methylene dicyclohexylcarbodiimide), and poly(isophoronecarbodiimide); and poly(phenylenecarbodiimide) and poly(naphthylcarbodiimide). Poly(tolylcarbodiimide), poly(methyldiisopropylphenylcarbodiimide), poly(triethylphenylcarbodiimide), poly(diethylphenylcarbodiimide), poly(triisopropylphenylcarbodiimide), poly(diisopropylphenylcarbodiimide), poly(phenylene dimethylcarbodiimide), poly(tetramethylphenylene dimethylcarbodiimide), poly(methylene diphenylcarbodiimide), poly[methylene bis(methylphenylene)carbodiimide], and other aromatic polycarbodiimides, etc., are polycarbodiimides. These can be used individually or in combination of two or more.

[0134] Commercially available products as carbodiimide-based curing agents include, for example, Carbodilight V-03 (carbodiimide equivalent: 216 g / eq.), Carbodilight V-05 (carbodiimide equivalent: 262 g / eq.), Carbodilight V-07 (carbodiimide equivalent: 200 g / eq.), and Carbodilight V-09 (carbodiimide equivalent: 200 g / eq.) manufactured by Nisshinbo Kemikal Co., Ltd.; and Stabaczoru P (carbodiimide equivalent: 302 g / eq.) manufactured by Rancus Co., Ltd.

[0135] As phenolic curing agents, curing agents having one or more, preferably two or more, hydroxyl groups (phenolic hydroxyl groups) bonded to aromatic rings such as benzene rings or naphthalene rings in one molecule can be used. From the viewpoint of heat resistance and water resistance, phenolic curing agents having a phenolic varnish structure are preferred. Furthermore, from the viewpoint of adhesion to the adhered substrate, nitrogen-containing phenolic curing agents are preferred, and phenolic curing agents containing a triazine skeleton are more preferred. Among these, from the viewpoint of highly satisfying heat resistance, water resistance, and adhesion, phenolic varnish resins containing a triazine skeleton are preferred. These can be used alone or in combination of two or more.

[0136] Specific examples of phenol-based and naphthol-based curing agents include, for instance, “MEH-7700”, “MEH-7810”, and “MEH-7851” manufactured by Meiwa Chemical Co., Ltd.; “NHN”, “CBN”, and “GPH” manufactured by Nippon Kayaku Co., Ltd.; “SN170”, “SN180”, “SN190”, “SN475”, “SN485”, “SN495”, “SN-495V”, “SN375”, and “SN395” manufactured by Nippon Steel Kemical & Materia Co., Ltd.; and “TD-2090”, “LA-7052”, “LA-7054”, “LA-1356”, “LA-3018-50P”, and “EXB-9500” manufactured by DIC Co., Ltd.

[0137] As an anhydride-based curing agent, examples include curing agents having one or more anhydride groups per molecule, preferably curing agents having two or more anhydride groups per molecule. Specific examples of anhydride-based curing agents include phthalic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, methyltetrahydrophthalic anhydride, methylhexahydrophthalic anhydride, methylnadic anhydride, hydrogenated methylnadic anhydride, trialkyltetrahydrophthalic anhydride, dodecenylsuccinic anhydride, 5-(2,5-dioxotetrahydro-3-furanyl)-3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride, trimellitic anhydride, and pyromellitic acid. Anhydrides, such as benzophenone tetracarboxylic dianhydride, biphenyl tetracarboxylic dianhydride, naphthalene tetracarboxylic dianhydride, oxydiphthalic dianhydride, 3,3'-4,4'-diphenylsulfone tetracarboxylic dianhydride, 1,3,3a,4,5,9b-hexahydro-5-(tetrahydro-2,5-dioxo-3-furanyl)-naphtho[1,2-C]furan-1,3-dione, ethylene glycol bis(triphenylamine), and styrene-maleic acid copolymer resins, etc., are polymeric anhydrides. These can be used individually or in combination of two or more.

[0138] Commercially available anhydride-based curing agents include: "HNA-100", "MH-700", "MTA-15", "DDSA", and "OSA" manufactured by Shin Nippon Rika Co., Ltd.; "YH-306" and "YH-307" manufactured by Mitsubishi Chemical Co., Ltd.; "HN-2200" and "HN-5500" manufactured by Resonack Co., Ltd.; and "EF-30", "EF-40", "EF-60", and "EF-80" manufactured by Clayvale Co., Ltd. These can be used individually or in combination of two or more.

[0139] Examples of amine-based curing agents include those having one or more, preferably two or more, amino groups in one molecule. The amino groups in the amine-based curing agent are preferably primary or secondary amino groups, more preferably primary amino groups. Examples of amine-based curing agents include aliphatic amines, polyether amines, alicyclic amines, and aromatic amines, among which aromatic amines are preferred from the viewpoint of achieving the desired effect of the present invention. Primary or secondary amines are preferred, more preferably primary amines.

[0140] Specific examples of amine-based curing agents include 4,4'-methylenebis(2,6-dimethylaniline), 4,4'-diaminodiphenylmethane, 4,4'-diaminodiphenyl sulfone, 3,3'-diaminodiphenyl sulfone, m-phenylenediamine, m-phenylenediamine, diethyltoluenediamine, 4,4'-diaminodiphenyl ether, 3,3'-dimethyl-4,4'-diaminobiphenyl, 2,2'-dimethyl-4,4'-diaminobiphenyl, 3,3'-dihydroxybenzidine, and 2,2-bis(3-amino-4-hydroxy) 2,2-bis(4-aminophenyl)propane, 3,3-dimethyl-5,5-diethyl-4,4-diphenylmethanediamine, 2,2-bis(4-aminophenyl)propane, 2,2-bis(4-(4-aminophenoxy)phenyl)propane, 1,3-bis(3-aminophenoxy)benzene, 1,3-bis(4-aminophenoxy)benzene, 1,4-bis(4-aminophenoxy)benzene, 4,4'-bis(4-aminophenoxy)biphenyl, bis(4-(4-aminophenoxy)phenyl)sulfone, bis(4-(3-aminophenoxy)phenyl)sulfone, etc. Amine-based curing agents can be commercially available, such as SEIKACURE-S from Seika Corporation, KAYABOND C-200S, KAYABOND C-100, KAYABOND AA, KAYABOND AB, and KAYABOND AS from Nippon Kayaku Co., Ltd., Epicure W from Mitsubishi Chemical Co., Ltd., and DTDA from Sumitomo Seika Co., Ltd. These can be used individually or in combination of two or more.

[0141] Specific examples of benzoxazine-based curing agents include "JBZ-OP100D" and "ODA-BOZ" manufactured by JFE Chemicals; "HFB2006M" manufactured by Showa Polymers; and "Pd" and "Fa" manufactured by Shikoku Chemical Industry Co., Ltd. These can be used individually or in combination of two or more.

[0142] Examples of cyanate ester curing agents include, for example, bisphenol A dicyanate, polyphenol cyanate, oligomeric (3-methylene-1,5-phenylene cyanate), 4,4'-methylenebis(2,6-dimethylphenyl cyanate), 4,4'-ethylene diphenyl dicyanate, hexafluorobisphenol A dicyanate, 2,2-bis(4-cyanate-phenyl)propane, 1,1-bis(4-cyanate-phenylmethane), bis(4-cyanate-3,5-dimethylphenyl)methane, 1,3-bis(4-cyanate-phenyl-1-(methylethylene))benzene, bis(4-cyanate-phenyl) sulfide, and bis(4-cyanate-phenyl) ether, as well as multifunctional cyanate ester resins derived from phenolic varnishes and cresol varnishes, and some triazine-modified prepolymers of these cyanate ester resins. Commercially available cyanate ester-based curing agents include Arxada's "PT-30", "PT-60" (phenolic varnish-type multifunctional cyanate ester resin), "ULL-950S" (multifunctional cyanate ester resin), "BA-230", and "BA-230S75" (prepolymers that have become part or all of the triazineized trimer of bisphenol A dicyanate). These can be used alone or in combination of two or more.

[0143] Examples of thiol-based curing agents include trimethylolpropane tris(3-mercaptopropionate), pentaerythritol tetra(3-mercaptobutyrate), and tris(3-mercaptopropyl)isocyanurate. These can be used individually or in combination of two or more.

[0144] Regarding the ratio of (A) a cyclic ether compound with a four-membered ring or less to (B) a curing agent, from the viewpoint of significantly obtaining the effects of the present invention, the ratio of [total number of functional groups of component (A)] to [total number of functional groups of component (B)] is preferably in the range of 1:0.01 to 1:10, more preferably 1:0.3 to 1:5, and even more preferably 1:0.5 to 1:3. Here, "total number of functional groups of component (A)" is the sum of all values ​​obtained by dividing the mass of the non-volatile components of component (A) present in the resin composition by the functional group equivalent of component (A). Similarly, "total number of functional groups of component (B)" is the sum of all values ​​obtained by dividing the mass of the non-volatile components of component (B) present in the resin composition by the functional group equivalent of component (B).

[0145] Regarding the content of component (B), from the viewpoint of significantly obtaining the effects of the present invention, when the non-volatile component in the resin composition is set to 100% by mass, it is preferably 1% by mass or more, more preferably 2% by mass or more or 3% by mass or more, further preferably 4% by mass or more or 5% by mass or more, and particularly preferably 6% by mass or more or 7% by mass or more. In another embodiment, it may be 8% by mass or more, 9% by mass or more, 10% by mass or more, 11% by mass or more, 12% by mass or more, etc. The upper limit is preferably 50% by mass or less or 45% by mass or less, more preferably 40% by mass or less or 35% by mass or less, further preferably 30% by mass or less or 25% by mass or less, and particularly preferably 20% by mass or less, 15% by mass or less or 13% by mass or less.

[0146] Regarding the content of component (B), from the viewpoint of significantly obtaining the effects of the present invention, when the resin component in the resin composition is set to 100% by mass, it is preferably 5% by mass or more or 10% by mass or more, more preferably 15% by mass or more or 18% by mass or more, further preferably 20% by mass or more or 22% by mass or more, and particularly preferably 24% by mass or more or 25% by mass or more. In one embodiment, it may be 26% by mass or more, 28% by mass or more, etc. The upper limit is preferably 80% by mass or less or 75% by mass or less, more preferably 70% by mass or less, 65% by mass or less or 60% by mass or less, further preferably 55% by mass or less, 50% by mass or less or 45% by mass or less, and particularly preferably 40% by mass or less, 35% by mass or less or 32% by mass or less.

[0147] Regarding the total content of components (A) and (B), from the viewpoint of significantly obtaining the effects of the present invention, when the non-volatile component in the resin composition is set to 100% by mass, it is preferably 2% by mass or more, more preferably 5% by mass or more or 10% by mass or more, further preferably 15% by mass or more or 20% by mass or more, and particularly preferably 22% by mass or more or 24% by mass or more. In another embodiment, it may be 25% by mass or more, 28% by mass or more, 30% by mass or more, 32% by mass or more, 34% by mass or more, 36% by mass or more, 38% by mass or more, etc. The upper limit is preferably 70% by mass or less or 65% by mass or less, more preferably 60% by mass or less or 55% by mass or less, further preferably 50% by mass or less or 48% by mass or less, and particularly preferably 45% by mass or less, 42% by mass or less, or 40% by mass or less.

[0148] Regarding the mass ratio of component (A1) to component (B) [(A1) component / (B) component], from the viewpoint of significantly obtaining the effects of the present invention, it is preferably 0.001 or more or 0.002 or more, more preferably 0.005 or more or 0.008 or more, further preferably 0.01 or more or 0.015 or more, and particularly preferably 0.02 or more, 0.05 or more, or 0.07 or more. Regarding the upper limit, from the viewpoint of reducing the coefficient of linear expansion of the cured product and increasing the glass transition temperature of the cured product, it is preferably 10 or less, more preferably 8 or less or 5 or less, further preferably 2 or less or 1 or less, and particularly preferably 0.8 or less, 0.6 or less, or 0.5 or less. Additionally, in one embodiment, it may be 0.4 or less, 0.3 or less, 0.2 or less, 0.1 or less, 0.08 or less, etc.

[0149] When the resin composition of the first embodiment contains component (A2), from the viewpoint of significantly obtaining the effects of the present invention, the mass ratio of component (B) to component (A2) [component (B) / (A2)] is preferably 0.001 or more, more preferably 0.01 or more or 0.02 or more, further preferably 0.05 or more, 0.08 or more, or 0.1 or more, and particularly preferably 0.2 or more, 0.3 or more, or 0.4 or more. The upper limit is preferably 10 or less, more preferably 8 or less or 5 or less, further preferably 2 or less or 1 or less, and particularly preferably 0.8 or less or 0.7 or less. In another embodiment, it may be 0.6 or less, 0.5 or less, etc.

[0150] Regarding the mass ratio of component (B) to component (A) [component (B) / (component (A)], from the viewpoint of significantly obtaining the effects of the present invention, it is preferably 0.001 or more or 0.005 or more, more preferably 0.01 or more or 0.02 or more, further preferably 0.05 or more or 0.08 or more, and particularly preferably 0.1 or more, 0.2 or more, or 0.3 or more. In one embodiment, it may be 0.4 or more, etc. The upper limit is preferably 10 or less or 8 or less, more preferably 5 or less or 2 or less, further preferably 1 or less or 0.8 or less, and particularly preferably 0.6 or less or 0.5 or less.

[0151] <(C) Inorganic filler materials>

[0152] The resin composition of the first embodiment of the present invention contains an inorganic filler (C). Inorganic compounds can be used as the inorganic filler (C). Examples of inorganic fillers (C) include silica, alumina, aluminosilicates, glass powder, cordierite, 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, silica or alumina is preferred, and silica is more preferred. That is, in one embodiment, component (C) preferably includes at least one selected from silica and alumina, and silica is more preferred. Examples of silica include amorphous silica, fused silica, crystalline silica, synthetic silica, and hollow silica. Furthermore, spherical silica is preferred as the shape of the silica. (C) The inorganic filler material can be used alone or in combination of two or more in any ratio.

[0153] In one embodiment, (C) the inorganic filler material preferably comprises an inorganic oxide. Examples of inorganic oxides include silicon dioxide, alumina, glass powder, zinc oxide, magnesium oxide, titanium oxide, and zirconium oxide. Silicon dioxide, alumina, or glass powder are preferred, silicon dioxide or alumina are more preferred, and silicon dioxide is even more preferred. In another embodiment, (C) the inorganic filler material may comprise alumina, or it may comprise both silicon dioxide and alumina.

[0154] Commercially available products as (C) inorganic filler materials include, for example, "SP60-05" and "SP507-05" manufactured by Nippon Steel Kemical & Materia; "YC100C", "YA050C", "YA050C-MJE", "YA010C", "SC2500SQ", "SO-C4", "SO-C2", "SO-C1", and "SC2300-SVJ" manufactured by AdMatex. SC2050-SXF, 180nmSX-C1; Denka Corporation's UFP-30, DAW-03, FB-105FD, ASFP-40, FB-5SDC; Tokuyama Corporation's Silver NSS-3N, Silver NSS-4N, Silver NSS-5N; Pacific Cement Corporation's Silver Fies, MGH-005, etc.

[0155] Regarding the average particle size of the inorganic filler (C), from the viewpoint of increasing the glass transition temperature of the cured material, it is preferably 10.0 μm or less, more preferably 5.0 μm or less, further preferably 2.0 μm or less, even more preferably 1.0 μm or less, and particularly preferably 0.7 μm or less or 0.6 μm or less. There is no particular limitation on the lower limit of the average particle size of the inorganic filler (C), but it is preferably 0.01 μm or more, more preferably 0.05 μm or more, further preferably 0.1 μm or more, and particularly preferably 0.15 μm or more or 0.2 μm or more. The average particle size of the inorganic filler (C) can be determined by laser diffraction and scattering based on the Mie scattering theory. Specifically, the particle size distribution of the inorganic filler can be established using a laser diffraction and scattering particle size distribution measuring device, with the median diameter as the average particle size, and then measured. For the sample to be measured, a product can be prepared by weighing 100 mg of inorganic filler and 10 g of methyl ethyl ketone into a vial and dispersing it ultrasonically for 10 minutes. The wavelength of the light source used in the laser diffraction particle size distribution measuring device can be set to cyan or red, and the measurement can be performed using a flow cell method. Examples of laser diffraction particle size distribution measuring devices include, for example, the "LA-960" manufactured by Horiba Corporation.

[0156] Regarding the specific surface area of ​​the (C) inorganic filler material, from the viewpoint of using the (1D) aluminum complex as a Lewis acid catalyst and adjusting the number of hydroxyl groups on the surface of the (C) inorganic filler material that reacts with the (A1) component, 0.1 m² is preferred. 2 / g or more, preferably 0.5m 2 / g or more, further preferably 1m 2 / g or more or 3m 2 / g or more. (C) The upper limit of the specific surface area of ​​the inorganic filler material is preferably 100m². 2 / g or less, preferably 70m 2 / g or less, more preferably 50m 2 / g or less, especially preferably 40m 2 / g or less, 35m 2 / g or less or 30m 2 / g or less. In one embodiment, the specific surface area of ​​the inorganic filler material (C) is preferably 0.1 to 50 m². 2 / g. Regarding the specific surface area of ​​inorganic filler materials, it can be calculated using the BET method by using a specific surface area measuring device (Macsorb HM-1210 manufactured by Macsorb Corporation) to adsorb nitrogen gas onto the sample surface and then using the BET multi-point method.

[0157] (C) The inorganic filler material is preferably surface-treated with a surface treatment agent. Surface treatment improves the moisture resistance and dispersibility of the (C) inorganic filler material. Furthermore, it allows the (1D) aluminum complex to act as a Lewis acid catalyst and adjusts the number of hydroxyl groups on the surface of the (C) inorganic filler material reacting with the (A1) component. In one embodiment, the surface-treated inorganic filler material can be used in combination with the untreated inorganic filler material. When the surface-treated inorganic filler material is used in combination with the untreated inorganic filler material, the difference between the dielectric loss tangent (Df) at high temperature (100°C) and at room temperature (23°C) (temperature dependence of the dielectric loss tangent) can be reduced.

[0158] As surface treatment agents, examples include vinyl silane coupling agents such as vinyltrimethoxysilane and vinyltriethoxysilane; epoxy silane coupling agents such as 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, and 3-glycidoxypropyltriethoxysilane; and styrene-based silane coupling agents such as p-styrenetrimethoxysilane; 3- Methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, 3-methacryloxypropyltriethoxysilane and other methacrylyl-based silane coupling agents; acrylyl-based silane coupling agents such as 3-acryloxypropyltrimethoxysilane; N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane, N-(2-aminoethyl)-3-aminopropyltrimethoxysilane, 3-aminopropyltrimethoxysilane Amino silane coupling agents such as tri(trimethoxysilylpropyl)isocyanurate and tri(trimethoxysilylpropyl)isocyanurate; ureoyl silane coupling agents such as tri(trimethoxysilylpropyl)isocyanurate and tri(ureopropyltrialkoxysilane); ureoyl silane coupling agents such as 3-aminopropyltriethoxysilane, 3-triethoxysilyl-N-(1,3-dimethylbutylene)propylamine, N-phenyl-3-aminopropyltrimethoxysilane, N-phenyl-8-aminooctyltrimethoxysilane, and N-(vinylbenzyl)-2-aminoethyl-3-aminopropyltrimethoxysilane; isocyanurate silane coupling agents such as tri(trimethoxysilylpropyl)isocyanurate; ureoyl silane coupling agents such as 3-ureopropyltrialkoxysilane. 3-Mercaptopropylmethyldimethoxysilane, 3-mercaptopropyltrimethoxysilane, and other mercapto-based silane coupling agents; 3-isocyanate-based silane coupling agents such as propyltriethoxysilane; 3-trimethoxysilylpropylsuccinic anhydride and other anhydride-based silane coupling agents; bis(triethoxysilylpropyl)tetrasulfide and other thioether-based silane coupling agents; other silane coupling agents, non-silane coupling-alkoxysilane compounds such as methyltrimethoxysilane and phenyltrimethoxysilane, organosilazane compounds, titanate-based coupling agents, etc. Furthermore, the surface treatment agent can be used alone or in combination of two or more in any ratio. In one embodiment, (C) the inorganic filler material is preferably surface-treated with an amino-based silane coupling agent, more preferably with N-phenyl-3-aminopropyltrimethoxysilane.

[0159] Regarding the degree of surface treatment using the surface treatment agent, from the viewpoint of improving the dispersibility of the inorganic filler material and from the viewpoint of using the (1D) aluminum complex as a Lewis acid catalyst to adjust the number of hydroxyl groups on the surface of the (C) inorganic filler material that reacts with the (A1) component, it is preferable to control it within a specified range. Specifically, it is preferable to surface treat 100 parts by mass of the inorganic filler material with 0.2 parts by mass to 5 parts by mass of the surface treatment agent, more preferably with 0.2 parts by mass to 3 parts by mass, and even more preferably with 0.3 parts by mass to 2 parts by mass.

[0160] The degree of surface treatment using surface treatment agents can be evaluated by the carbon content per unit surface area of ​​the inorganic filler. From the viewpoint of improving the dispersibility of the inorganic filler, a carbon content of 0.02 mg / m² per unit surface area is preferred. 2 More preferably 0.1 mg / m 2 The above is further optimized to 0.2 mg / m². 2 The above. The preferred upper limit is 1 mg / m³. 2 Below, 0.8 mg / m² is more preferred. 2 The following is a further preferred dosage: 0.5 mg / m² 2 the following.

[0161] Regarding the carbon content per unit surface area of ​​(C) inorganic filler materials, it can be determined by cleaning the surface-treated inorganic filler material with a solvent (e.g., methyl ethyl ketone (MEK)). Specifically, a sufficient amount of MEK is added to the inorganic filler material that has been surface-treated with a surface treatment agent, and the material is ultrasonically cleaned at 25°C for 5 minutes. After removing the supernatant and drying the solid components, the carbon content per unit surface area of ​​the inorganic filler material can be determined using a carbon analyzer. A carbon analyzer such as the "EMIA-320V" manufactured by Horiba Manufacturing Co., Ltd. can be used.

[0162] Regarding the content of component (C), when the non-volatile component in the resin composition is set to 100% by mass, from the viewpoints of significantly obtaining the effects of the present invention, further reducing the dielectric loss tangent of the cured product at room temperature (23°C) and high temperature (100°C), and reducing the coefficient of linear expansion of the cured product, it is preferably 10% by mass or more or 20% by mass or more, more preferably 30% by mass or more or 35% by mass or more, further preferably 40% by mass or more or 45% by mass or more, and particularly preferably 50% by mass or more or 55% by mass or more. The upper limit is preferably 95% by mass or less, more preferably 90% by mass or less, further preferably 85% by mass or less, and particularly preferably 80% by mass or less or 75% by mass or less. In addition, in one embodiment, it may be 70% by mass or less, 65% by mass or less, 60% by mass or less, etc.

[0163] Regarding the total content of components (A), (B), and (C), when the non-volatile component in the resin composition is set to 100% by mass, from the viewpoint of significantly obtaining the effects of the present invention, it is preferably 30% by mass or more or 40% by mass or more, more preferably 50% by mass or more or 60% by mass or more, further preferably 70% by mass or more, 80% by mass or more or 85% by mass or more, and particularly preferably 90% by mass or more, 95% by mass or more or 97% by mass or more. In one embodiment, it may be 98% by mass or more, 98.5% by mass or more, etc. The upper limit is preferably 99.9% by mass or less, more preferably 99.8% by mass or less, further preferably 99.5% by mass or less, and particularly preferably 99.2% by mass or less.

[0164] Regarding the mass ratio of component (A1) to component (C) [(A1) component / (C) component], from the viewpoint of significantly obtaining the effects of the present invention, it is preferably 0.0001 or more, more preferably 0.0002 or more or 0.0005 or more, further preferably 0.0008 or more or 0.001 or more, and particularly preferably 0.002 or more or 0.003 or more. Alternatively, in one embodiment, it may be 0.005 or more, 0.007 or more, 0.008 or more, 0.01 or more, 0.012 or more, 0.015 or more, etc. Regarding the upper limit, from the viewpoint of reducing the coefficient of linear expansion of the cured product, increasing the glass transition temperature of the cured product, and further reducing the dielectric loss tangent of the cured product at room temperature (23°C) and high temperature (100°C), it is preferably 1 or less, more preferably 0.8 or less, further preferably 0.5 or less or 0.2 or less, and particularly preferably 0.15 or less or 0.1 or less. In another embodiment, the value may be 0.08 or less, 0.05 or less, 0.04 or less, 0.03 or less, 0.02 or less, etc.

[0165] When the resin composition of the first embodiment contains component (A2), from the viewpoint of significantly obtaining the effects of the present invention, the mass ratio of component (A2) to component (C) [(A2) component / (C) component] is preferably 0.001 or more or 0.005 or more, more preferably 0.01 or more or 0.02 or more, further preferably 0.05 or more or 0.1 or more, and particularly preferably 0.15 or more or 0.2 or more. In another embodiment, it may be 0.25 or more, 0.3 or more, 0.35 or more, 0.4 or more, etc. The upper limit is preferably 20 or less or 10 or less, more preferably 8 or less or 5 or less, further preferably 2 or less or 1 or less, and particularly preferably 0.8 or less, 0.6 or less or 0.5 or less.

[0166] Regarding the mass ratio of component (B) to component (C) [component (B) / (C)], from the viewpoint of significantly obtaining the effects of the present invention, it is preferably 0.001 or more or 0.002 or more, more preferably 0.005 or more or 0.008 or more, further preferably 0.01 or more or 0.02 or more, and particularly preferably 0.05 or more, 0.08 or more, or 0.10 or more. Alternatively, in one embodiment, it may be 0.12 or more, 0.15 or more, 0.18 or more, 0.20 or more, etc. Regarding the upper limit, from the viewpoint of further reducing the dielectric loss tangent of the cured material at room temperature (23°C) and high temperature (100°C), and from the viewpoint of reducing the coefficient of linear expansion of the cured material, it is preferably 20 or less or 10 or less, more preferably 8 or less, 5 or less, or 2 or less, further preferably 1 or less, 0.8 or less, or 0.5 or less, and particularly preferably 0.4 or less, 0.3 or less, or 0.25 or less.

[0167] <(1D)aluminum complex>

[0168] The resin composition of the first embodiment of the present invention contains (1D) aluminum complexes. The (1D) aluminum complexes have a structure in which one or more ligands are coordinated to trivalent aluminum ions. The (1D) aluminum complexes can be used alone or in combination of two or more.

[0169] Examples of ligands for (1D) aluminum complexes include alcohols, alkoxides, phenols, phenol salts, β-diketones, β-diketone enolates, β-keto esters, β-keto ester enolates, carboxylic acids, carboxylic acid ions, water, hydroxide ions, oxygen atoms, ammonia, amines, and cyanide ions. Ligands preferably selected from alcohols, alkoxides, β-diketones, β-diketone enolates, β-keto esters, and β-keto ester enolates are preferred. Ligands more preferably selected from β-diketones, β-diketone enolates, β-keto esters, and β-keto ester enolates are even more preferred. That is, the (1D) component preferably includes one or more aluminum complexes selected from aluminum complexes having alkoxides as ligands, aluminum complexes having β-diketone enolates as ligands, and aluminum complexes having β-keto ester enolates as ligands.

[0170] (1D) aluminum complexes may have two or more different ligands. In one embodiment, the (1D) component preferably has one or more ligands selected from alcohols, alkoxides, β-diketones, β-diketone enolates, β-keto esters and β-keto ester enolates, and more preferably has two or more ligands selected from the above group.

[0171] The alcohol used as a ligand is preferably an alcohol with 1 to 20 carbon atoms. The lower limit for the number of carbon atoms in the alcohol is more preferably 2 or more, and even more preferably 3 or more. The lower limit for the number of carbon atoms in the alcohol is preferably 18 or less or 16 or less, more preferably 14 or less or 12 or less, even more preferably 10 or less or 8 or less, and particularly preferably 6 or less or 4 or less. Examples of alcohols include, for example, methanol, ethanol, n-propanol, isopropanol, n-butanol, sec-butanol, isobutanol, tert-butanol, pentanol, hexanol, etc., with ethanol, isopropanol, or sec-butanol being preferred, and isopropanol or sec-butanol being more preferred.

[0172] The alkoxide, as a ligand, is an anion formed by the removal of a hydrogen ion from the hydroxyl group of an alcohol. The number of carbon atoms in the alkoxide is preferably 1 to 20. The lower limit of the number of carbon atoms in the alkoxide is more preferably 2 or more, and even more preferably 3 or more. The lower limit of the number of carbon atoms in the alkoxide is more preferably 18 or less, 16 or less, 14 or less, or 12 or less, even more preferably 10 or less, or 8 or less, and particularly preferably 6 or less, or 4 or less. Examples of alkoxides include ethanol salts, ethanol salts, n-propanol salts, isopropanol salts, n-butanol salts, sec-butanol salts, isobutanol salts, tert-butanol salts, pentanol salts, and hexanol salts, with ethanol salts, isopropanol salts, or sec-butanol salts being preferred, and isopropanol salts or sec-butanol salts being more preferred.

[0173] The β-diketone used as a ligand is preferably a β-diketone with 5 to 20 carbon atoms. That is, the lower limit of the number of carbon atoms in the β-diketone is preferably 5 or more. The upper limit of the number of carbon atoms in the β-diketone, as described above, is preferably 20 or less, more preferably 18 or less, 16 or less, or 14 or less, even more preferably 12 or less, or 10 or less, and particularly preferably 8 or less, or 6 or less. In one embodiment, the number of carbon atoms in the β-diketone is preferably 5.

[0174] In one embodiment, the β-diketone is preferably a compound represented by the following formula (1d-1).

[0175]

Chemistry 4

[0176]

[0177] (In equation (1d-1), R) d1 and R d2 Each can independently represent an alkyl group with 1 to 10 carbon atoms, or an aryl group with 1 to 10 carbon atoms, which may have halogen atoms as substituents. R d3 (This refers to a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 1 to 10 carbon atoms.)

[0178] In equation (1d-1), R d1 and R d2 Each can independently represent an alkyl group with 1 to 10 carbon atoms, or an aryl group with 1 to 10 carbon atoms, which may have halogen atoms as substituents. R d1and R d2 They can be the same or different.

[0179] As R d1 and R d2 The alkyl group may have halogen atoms as substituents, including alkyl groups with halogen atoms as substituents and alkyl groups without halogen atoms as substituents, with alkyl groups without halogen atoms as substituents being preferred. Hereinafter, "alkyl group without halogen atoms as substituents" will be simply referred to as "alkyl". The alkyl group is a chain (straight-chain or branched) alkyl group or a cyclic alkyl group. The number of carbon atoms in the alkyl group is preferably 1 to 10, more preferably 1 to 5, further preferably 1 to 3, and particularly preferably 1. Examples of chain alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, hexyl, 2-ethylhexyl, octyl, decyl, etc., with methyl, ethyl, n-propyl, or isopropyl being preferred, more preferably methyl or ethyl, and further preferably methyl. Additionally, examples of cyclic alkyl groups include cyclopentyl, cyclohexyl, cyclooctyl, etc.

[0180] Regarding the halogen atom that serves as a substituent, examples include fluorine atom, chlorine atom, bromine atom, and iodine atom, with fluorine atom, chlorine atom, or bromine atom being preferred, fluorine atom or chlorine atom being more preferred, and fluorine atom being even more preferred.

[0181] Regarding alkyl groups having halogen atoms as substituents, among the preferred embodiments of the alkyl groups described above, those in which some or all of the hydrogen atoms are replaced with halogen atoms are preferred. Examples of alkyl groups having halogen atoms as substituents include trifluoromethyl, pentafluoroethyl, and trichloromethyl, with trifluoromethyl being preferred.

[0182] R d1 and R d2 The aryl group in [the compound name] is a group formed by removing a hydrogen atom from an aromatic ring in an aromatic compound. As R [the group name], [the aryl group name] is a group formed by removing a hydrogen atom from an aromatic ring in an aromatic compound. d1 and R d2 The aryl group of the substituent preferably has 1 to 10 carbon atoms, more preferably 3 to 10, even more preferably 5 to 10, and particularly preferably 6 to 10. Examples of aryl groups include phenyl, naphthyl, thiophene, pyrrole, furanyl, furanyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, pyrrolidinyl, piperidinyl, quinolinyl, isoquinolinyl, etc., with phenyl, naphthyl, furanyl, or thiophene being preferred, more preferably phenyl, furanyl, or thiophene, and even more preferably phenyl.

[0183] Of these, R d1 and R d2 Methyl, trifluoromethyl, or phenyl are preferred, with methyl being more preferred.

[0184] In equation (1d-1), R d3R represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms that may have halogen atoms as substituents, or an aryl group having 1 to 10 carbon atoms. d3 The preferred scheme of alkyl groups in R d1 and R d2 The alkyl groups are the same. R d3 The preferred scheme of aryl group and R d1 and R d2 The aryl groups are the same in these. Among them, R d3 Hydrogen atoms or methyl groups are preferred, with hydrogen atoms being more preferred.

[0185] Specific examples of β-diketones include acetylacetone, benzoylacetone, dibenzoylmethane, 2-furoylbenzoylmethane, trifluoroacetylacetone, 2-furoyltrifluoroacetone, and 2-furoyltrifluoroacetone, with acetylacetone being preferred.

[0186] The β-diketenolide, as a ligand, is an anion generated by the dissociation of the hydrogen ion at the α-position of the β-diketone. The number of carbon atoms in the β-diketenolide is preferably 5 to 20. That is, the lower limit of the number of carbon atoms in the β-diketenolide is preferably 5 or more. The upper limit of the number of carbon atoms in the β-diketenolide, as described above, is preferably 20 or less, more preferably 18 or less, 16 or less, or 14 or less, further preferably 12 or less, or 10 or less, and particularly preferably 8 or less, or 6 or less. In one embodiment, the number of carbon atoms in the β-diketenolide is preferably 5.

[0187] In one embodiment, the β-diketenolide is preferably an anion represented by the following formula (1d-2).

[0188]

Transformation 5

[0189]

[0190] (In equation (1d-2), R) d1 and R d2 Each can independently represent an alkyl group having 1 to 10 carbon atoms as substituents, or an aryl group having 1 to 10 carbon atoms as substituents. R d3 (This refers to a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 1 to 10 carbon atoms.)

[0191] In equation (1d-2), R d1 and R d2 Each independently represents an alkyl group with 1 to 10 carbon atoms, or an aryl group with 1 to 10 carbon atoms, which may have halogen atoms as substituents, and R in formula (1d-1)d1 and R d2 same.

[0192] In equation (1d-2), R d3 Represents a hydrogen atom, an alkyl group with 1 to 10 carbon atoms that may have halogen atoms as substituents, or an aryl group with 1 to 10 carbon atoms, and R in formula (1d-1). d3 same.

[0193] Generally, β-diketenolides are known to have resonance structures represented by formula (1d-2-1) and formula (1d-2-2), with negative charge delocalization, and are therefore sometimes represented as in formula (1d-2-3). In this specification, when one of the resonance structures is described as in formula (1d-2), it also implies negative charge delocalization of the β-diketenolide. That is, formula (1d-2) and formula (1d-2-3) represent the same structure and electronic state.

[0194]

Transformation 6

[0195]

[0196]

Transformation 7

[0197]

[0198] Specific examples of β-diketenolides include anions represented by the formulas (1d-2-4) to (1d-2-10), with anions represented by formula (1d-2-4) being preferred.

[0199]

Transformation 8

[0200]

[0201] The β-keto ester used as a ligand is preferably a β-keto ester with 5 to 20 carbon atoms. The upper limit of the number of carbon atoms in the β-keto ester, as described above, is preferably 20 or less, more preferably 18 or less, 16 or less, or 14 or less, further preferably 12 or less, or 10 or less, and particularly preferably 8 or less, or 7 or less. The lower limit of the number of carbon atoms in the β-keto ester, as described above, is preferably 5 or more, more preferably 6 or more. In one embodiment, the number of carbon atoms in the β-keto ester is preferably 6.

[0202] In one embodiment, the β-keto ester is preferably a compound represented by the following formula (1d-3).

[0203]

Chemistry 9

[0204]

[0205] (In equation (1d-3), R)d4 and R d5 Each can independently represent an alkyl group with 1 to 10 carbon atoms, or an aryl group with 1 to 10 carbon atoms, which may have halogen atoms as substituents. R d6 (This refers to a hydrogen atom, an alkyl group with 1 to 10 carbon atoms that may have halogen atoms as substituents, or an aryl group with 1 to 10 carbon atoms.)

[0206] In equation (1d-3), R d4 and R d5 Each can independently represent an alkyl group with 1 to 10 carbon atoms, or an aryl group with 1 to 10 carbon atoms, which may have halogen atoms as substituents. R d4 and R d5 They can be the same or different.

[0207] As R d4 and R d5 The alkyl group may have halogen atoms as substituents, including alkyl groups with halogen atoms as substituents and alkyl groups without halogen atoms as substituents, with alkyl groups without halogen atoms as substituents being preferred. The alkyl group is a chain (straight-chain or branched) alkyl group or a cyclic alkyl group. The number of carbon atoms in the alkyl group is preferably 1 to 10, more preferably 1 to 5, further preferably 1 to 3, and particularly preferably 1 or 2. Examples of chain alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, hexyl, 2-ethylhexyl, octyl, decyl, etc., with methyl, ethyl, n-propyl, isopropyl, or n-butyl being preferred, and methyl or ethyl being more preferred. In addition, examples of cyclic alkyl groups include cyclopentyl, cyclohexyl, cyclooctyl, etc.

[0208] Regarding the halogen atom that serves as a substituent, examples include fluorine atom, chlorine atom, bromine atom, and iodine atom, with fluorine atom, chlorine atom, or bromine atom being preferred, fluorine atom or chlorine atom being more preferred, and fluorine atom being even more preferred.

[0209] Regarding alkyl groups having halogen atoms as substituents, among the preferred embodiments of the alkyl groups described above, those in which some or all of the hydrogen atoms are replaced with halogen atoms are preferred. Examples of alkyl groups having halogen atoms as substituents include trifluoromethyl, pentafluoroethyl, and trichloromethyl, with trifluoromethyl being preferred.

[0210] R d4 and R d5 The aryl group in R is a group formed by removing a hydrogen atom from an aromatic ring in an aromatic compound. d4 and R d5The aryl group, which serves as a substituent, preferably has 1 to 10 carbon atoms, more preferably 3 to 10, even more preferably 5 to 10, and particularly preferably 6 to 10. Examples of aryl groups include phenyl, naphthyl, thiophene, pyrrole, furanyl, furanyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, pyrrolidinyl, piperidinyl, quinolinyl, and isoquinolinyl, with phenyl, naphthyl, furanyl, or thiophene being preferred, more preferably phenyl, furanyl, or thiophene, and even more preferably phenyl.

[0211] Of these, R d4 Preferably methyl, ethyl, n-propyl, or n-butyl, more preferably ethyl. d5 Methyl, trifluoromethyl, or phenyl are preferred, with methyl being more preferred.

[0212] In equation (1d-3), R d6 Represents a hydrogen atom, an alkyl group with 1 to 10 carbon atoms that may have halogen atoms as substituents, or an aryl group with 1 to 10 carbon atoms, and R in formula (1d-1). d3 same.

[0213] Specific examples of β-keto esters include, for example, methyl acetoacetate, ethyl acetoacetate, n-propyl acetoacetate, n-butyl acetoacetate, and compounds represented by the following formulas (1d-3-1) to (1d-3-8), with ethyl acetoacetate being preferred.

[0214]

Chemistry 10

[0215]

[0216] The β-keto ester enolide, serving as a ligand, is an anion generated by the dissociation of the hydrogen ion at the α-position of the β-keto ester. The β-keto ester preferably has 5 to 20 carbon atoms. The upper limit of the carbon number of the β-keto ester enolide, as described above, is preferably 20 or less, more preferably 18 or less, 16 or less, or 14 or less, even more preferably 12 or less, or 10 or less, and particularly preferably 8 or less, or 7 or less. The lower limit of the carbon number of the β-keto ester enolide, as described above, is preferably 5 or more, more preferably 6 or more. In one embodiment, the β-keto ester enolide preferably has 6 carbon atoms.

[0217] In one embodiment, the β-keto ester enolide is preferably an anion represented by the following formula (1d-4).

[0218]

Chemistry 11

[0219]

[0220] (In equation (1d-4), R) d4 and R d5Each can independently represent an alkyl group with 1 to 10 carbon atoms, or an aryl group with 1 to 10 carbon atoms, which may have halogen atoms as substituents. R d6 (This refers to a hydrogen atom, an alkyl group with 1 to 10 carbon atoms that may have halogen atoms as substituents, or an aryl group with 1 to 10 carbon atoms.)

[0221] In equation (1d-4), R d4 and R d5 Each can independently represent an alkyl group with 1 to 10 carbon atoms, or an aryl group with 1 to 10 carbon atoms, which may have halogen atoms as substituents, and R in formula (1d-3) d4 and R d5 same.

[0222] In equation (1d-4), R d6 Represents a hydrogen atom, an alkyl group with 1 to 10 carbon atoms that may have halogen atoms as substituents, or an aryl group with 1 to 10 carbon atoms, and R in formula (1d-1). d3 same.

[0223] Generally, β-keto ester enolates are known to have resonance structures represented by formula (1d-4-1) and formula (1d-4-2), with negative charge delocalization, and are therefore sometimes represented as in formula (1d-4-3). In this specification, when one of the resonance structures is described as in formula (1d-4), it also implies negative charge delocalization of the β-keto ester enol. That is, formula (1d-4) and formula (1d-4-3) represent the same structure and electronic state.

[0224]

Chemistry 12

[0225]

[0226]

Chemistry 13

[0227]

[0228] Specific examples of β-keto ester enolates include, for example, methyl acetoacetate, ethyl acetoacetate, n-propyl acetoacetate, n-butyl acetoacetate, anions represented by the following formulas (1d-4-4) to (1d-4-11), etc., with ethyl acetoacetate being preferred.

[0229]

Chemistry 14

[0230]

[0231] The carboxylic acid used as a ligand is preferably a carboxylic acid with 1 to 40 carbon atoms. The lower limit of the number of carbon atoms in the carboxylic acid is as described above, preferably 1 or more, more preferably 2 or 3 or more, further preferably 4 or 5 or more, and particularly preferably 6 or 7 or more. The upper limit of the number of carbon atoms in the carboxylic acid is as described above, preferably 40 or less, more preferably 36 or less, 32 or less, or 28 or less, further preferably 26 or less, or 24 or less, and particularly preferably 22 or less, or 20 or less. Examples of carboxylic acids include formic acid, acetic acid, propionic acid, butyric acid, valeric acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, lauric acid, palmitic acid, stearic acid, etc., with octanoic acid or stearic acid being preferred.

[0232] The carboxylic acid ion, as a ligand, is an anion generated by the dissociation of hydrogen ions from the carboxyl group of a carboxylic acid. The number of carbon atoms in the carboxylic acid ion is preferably 1 to 40. The lower limit of the number of carbon atoms in the carboxylic acid ion, as described above, is preferably 1 or more, more preferably 2 or 3 or more, further preferably 4 or 5 or more, and particularly preferably 6 or 7 or more. The upper limit of the number of carbon atoms in the carboxylic acid ion, as described above, is preferably 40 or less, more preferably 36 or less, 32 or less, or 28 or less, further preferably 26 or less or 24 or less, and particularly preferably 22 or less or 20 or less. Examples of carboxylic acid ions include, for example, formic acid ions, acetate ions, propionic acid ions, butyrate ions, valerate ions, hexanoate ions, heptanoate ions, octanoate ions, nonanoate ions, decanoate ions, laurate ions, palmitic acid ions, stearate ions, etc., with octanoate ions or stearate ions being preferred.

[0233] In one embodiment, the (1D) aluminum complex preferably comprises an aluminum chelate complex. By using a bidentate or more ligand in the ligand described above, the (1D) component can be an aluminum chelate complex. The ligand of the aluminum chelate complex preferably comprises a bidentate ligand. Examples of bidentate ligands include β-diketones, β-diketone enolates, β-keto esters, and β-keto ester enolates.

[0234] The (1D) aluminum complex can be a mononuclear aluminum complex containing one aluminum ion per molecule, or a polynuclear aluminum complex containing two or more aluminum ions per molecule. In one embodiment, the (1D) component preferably comprises a mononuclear aluminum complex.

[0235] (1D) The coordination number of the aluminum complex is preferably 1 to 12. Wherein, if one of the bidentate ligands coordinates, the coordination number is considered to be 2. The lower limit of the coordination number, as described above, is preferably 1 or more, more preferably 2 or more, further preferably 3 or more, and may be 4 or more, or 5 or more. The upper limit of the coordination number, as described above, is preferably 12 or less, more preferably 10 or less, further preferably 8 or less, and particularly preferably 7 or less. In one embodiment, the coordination number of the aluminum complex is preferably 6.

[0236] The number of ligands in the (1D) aluminum complex is preferably 1 to 12. Where one of the bidentate ligands coordinates, the number of ligands is considered to be 1. The lower limit of the number of ligands is as described above, preferably 1 or more, more preferably 2 or more, and even more preferably 3 or more. The upper limit of the number of ligands is as described above, preferably 12 or less, more preferably 10 or less or 8 or less, even more preferably 6 or less, and particularly preferably 5 or less or 4 or less. In one embodiment, the number of ligands in the (1D) aluminum complex is preferably 3.

[0237] The molecular weight of the (1D) aluminum complex is preferably 100 to 2000. The lower limit of the molecular weight of the (1D) aluminum complex, as described above, is preferably 100 or more, more preferably 120 or more or 140 or more, further preferably 160 or more or 180 or more, and particularly preferably 200 or more or 210 or more. The upper limit, as described above, is preferably 2000 or less, more preferably 1500 or less, 1000 or less or 900 or less, further preferably 800 or less, 700 or less or 600 or less, and particularly preferably 500 or less, 450 or less or 400 or less.

[0238] Specific examples of (1D) aluminum complexes include triisopropoxyaluminum (an aluminum complex represented by formula (1d-5-1)), diisopropoxyaluminum monosec-butoxy (an aluminum complex represented by formula (1d-5-2)), trisec-butoxyaluminum (an aluminum complex represented by formula (1d-5-3)), triethoxyaluminum (an aluminum complex represented by formula (1d-5-4)), ethyl acetoacetate diisopropoxyaluminum (an aluminum complex represented by formula (1d-5-5)), tri(ethyl acetoacetate)aluminum (an aluminum complex represented by formula (1d-5-6)), and alkyl acetoacetate diisopropoxyaluminum (an aluminum complex represented by formula (1d-5-6)). Aluminum complexes, such as those represented by formula (-7), monoacetylacetone bis(ethyl acetoacetate)aluminum (aluminum complex represented by formula (1d-5-8)), tri(acetylacetone)aluminum (aluminum complex represented by formula (1d-5-9)), cyclic isopropoxyaluminum oxide (aluminum complex represented by formula (1d-5-10)), cyclic aluminum stearate oxide (aluminum complex represented by formula (1d-5-11)), and cyclic aluminum octoate oxide (aluminum complex represented by formula (1d-5-12)), are preferred, with monoacetylacetone bis(ethyl acetoacetate)aluminum or diisopropoxyaluminum monosec-butyrate being more preferred. The above-mentioned aluminum complexes may exist in the resin composition in a partially dissociated state of the ligand.

[0239]

Chemistry 15

[0240]

[0241] (In equation (1d-5-7), R) d0 (Indicates an alkyl group.)

[0242] Examples of commercially available products of the (1D) aluminum complex include "AIPD" and "PADM" manufactured by Kawaken Facility Co., Ltd. , "AMD", "ASBD", "アルミキニウムエトキサイド", "ALCH", "S-75P", "ALC "H-TR", "アルミキレートM", "アルミキレートD", "アルミキレートA", "アルミキレートA" ( a)", "アルゴマー", "アルゴマーS", "アルゴマー800AF", "アルゴマー1000SF", etc.

[0243] Regarding the content of component (1D), from the viewpoint of significantly obtaining the effects of the present invention, when the non-volatile component in the resin composition is set to 100% by mass, it is preferably 0.0001% by mass or more or 0.0005% by mass or more, more preferably 0.001% by mass or more or 0.002% by mass or more, further preferably 0.005% by mass or more or 0.008% by mass or more, and particularly preferably 0.01% by mass or more, 0.015% by mass or more, or 0.017% by mass or more. In addition, in one embodiment, it may be 0.02% by mass or more, 0.025% by mass or more, 0.03% by mass or more, 0.035% by mass or more, etc. The upper limit is preferably 2.00% by mass or less or 1.00% by mass or less, more preferably 0.80% by mass or less or 0.50% by mass or less, further preferably 0.20% by mass or less, 0.15% by mass or less, 0.10% by mass or less or 0.08% by mass or less, particularly preferably 0.07% by mass or less, 0.06% by mass or less, 0.05% by mass or less or 0.04% by mass or less. In one embodiment, regarding the content of the (1D) component, when the non-volatile component in the resin composition is set to 100% by mass, it is preferably 0.01 to 0.20% by mass, more preferably 0.01 to 0.15% by mass.

[0244] Regarding the content of component (1D), from the viewpoint of significantly obtaining the effects of the present invention, when the resin component in the resin composition is set to 100% by mass, it is preferably 0.001% by mass or more or 0.002% by mass or more, more preferably 0.005% by mass or more or 0.008% by mass or more, further preferably 0.01% by mass or more or 0.02% by mass or more, particularly preferably 0.05% by mass or more, 0.06% by mass or more, or 0.08% by mass or more. The upper limit is preferably 10% by mass or less or 8% by mass or less, more preferably 5% by mass or less or 2% by mass or less, further preferably 1% by mass or less, 0.8% by mass or less or 0.5% by mass or less, particularly preferably 0.2% by mass or less, 0.18% by mass or less, 0.15% by mass or less, 0.12% by mass or less, or 0.1% by mass or less.

[0245] In the resin composition of the first embodiment, considering the total content of components (A), (B), (C), and (1D), when the non-volatile components in the resin composition are set to 100% by mass, from the viewpoint of significantly obtaining the effects of the present invention, it is preferably 30% by mass or more or 40% by mass or more, more preferably 50% by mass or more or 60% by mass or more, further preferably 70% by mass or more, 80% by mass or more or 85% by mass or more, and particularly preferably 90% by mass or more, 95% by mass or more or 97% by mass or more. In another embodiment, it may be 98% by mass or more, 98.5% by mass or more, etc. The upper limit may be 100% by mass, and it may be 99.9% by mass or less, 99.8% by mass or less, 99.5% by mass or less, 99.2% by mass or less, etc.

[0246] Regarding the mass ratio of (1D) component to (A1) component [(1D) component / (A1) component], from the viewpoints of achieving the effects of the present invention, reducing the coefficient of linear expansion of the cured product, and increasing the glass transition temperature of the cured product, it is preferably 0.0001 or more or 0.0002 or more, more preferably 0.0005 or more or 0.0008 or more, further preferably 0.001 or more or 0.002 or more, and particularly preferably 0.005 or more, 0.006 or more, or 0.007 or more. In one embodiment, it may be 0.01 or more, 0.02 or more, 0.03 or more, etc. The upper limit is preferably 5 or less or 2 or less, more preferably 1 or less or 0.8 or less, further preferably 0.5 or less or 0.2 or less, and particularly preferably 0.1 or less, 0.08 or less, 0.06 or less, 0.05 or less, or 0.04 or less.

[0247] In the case where the resin composition of the first embodiment contains component (A2), from the viewpoint of significantly obtaining the effects of the present invention, the mass ratio of component (1D) to component (A2) [(1D) component / (A2) component] is preferably 1×10⁻⁶. -5 Above or 2×10 -5 The above is preferred, with 5×10 being more ideal. -5 Above or 8×10 -5 The above is further preferred to be 1×10 -4 Above, 2×10 -4 Above or 5×10 -4 The above is particularly preferred, with 8×10 -4 Above, 1×10 -3 or above 1.2×10 -3 The above. The upper limit is preferably below 1 or 5 × 10. -1 Hereinafter, 1×10 is more preferred. -1Below or 8×10 -2 The following is a further preferred option: 5×10 -2 Below, 2×10 -2 Below or 1×10 -2 The following is particularly preferred: 8×10 -3 Below, 5×10 -3 Below, 2×10 -3 Below, 1.8×10 -3 Below or 1.5×10 -3 the following.

[0248] From the viewpoint of significantly obtaining the effects of the present invention, the mass ratio of (1D) component to (A) component [(1D) component / (A) component] is preferably 1×10⁻⁶. -5 Above or 2×10 -5 The above is preferred, with 5×10 being more ideal. -5 Above, 8×10 -5 Above or 1×10 -4 The above is further preferred to be 2×10 -4 Above, 5×10 -4 Above or 8×10 -4 The above is particularly preferred, with 1×10 -3 Above, 1.1×10 -3 or above 1.2×10 -3 The above. The upper limit is preferably below 1 or 5 × 10. -1 Hereinafter, 1×10 is more preferred. -1 Below, 8×10 -2 Below or 5×10 -2 The following is a further preferred option: 2×10 -2 Below, 1×10 -2 Below or 8×10 -3 The following is particularly preferred: 5×10 -3 Below, 3×10 -3 Below, 2×10 -3 Below, 1.8×10 -3 Below or 1.5×10 -3 the following.

[0249] Regarding the mass ratio of component (1D) to component (B) [(1D) component / (B) component], from the viewpoint of significantly obtaining the effects of the present invention, 1×10⁻⁶ is preferred. -5 Above or 5×10 -5 The above is preferred to be 1×10 -4 Above or 2×10 -4 The above is further optimized to be 5×10 -4 Above or 8×10 -4The above is particularly preferred, with 1×10 -3 Above, 2×10 -3 Above or 2.5×10 -3 The above. The upper limit is preferably below 1 or 5 × 10. -1 Hereinafter, 1×10 is more preferred. -1 Below, 8×10 -2 Below or 5×10 -2 The following is a further preferred option: 2×10 -2 Below, 1×10 -2 Below or 8×10 -3 The following is particularly preferred: 6×10 -3 Below, 5×10 -3 Below, 4×10 -3 Below or 3×10 -3 the following.

[0250] Regarding the mass ratio of (1D) component to (C) component [(1D) component / (C) component], from the viewpoint of significantly obtaining the effects of the present invention, 1×10⁻⁶ is preferred. -5 The above is preferred, specifically 2×10 -5 Above or 5×10 -5 The above is further optimized to 8×10 -5 Above or 1×10 -4 The above is particularly preferred, with 2×10 -4 Above or 3×10 -4 That's all. Alternatively, in one embodiment, it can be 4 × 10. -4 Above, 5×10 -4 Above, 6×10 -4 The above, etc. Regarding the upper limit, from the viewpoint of further reducing the dielectric loss tangent of the cured material at room temperature (23°C) and high temperature (100°C) and from the viewpoint of reducing the linear expansion coefficient of the cured material, 1×10⁻⁶ is preferred. -1 Below or 8×10 -2 The following is more preferably 5×10 -2 Below or 2×10 -2 Hereinafter, 1×10 is further preferred. -2 Below, 8×10 -3 Below or 5×10 -3 The following is particularly preferred: 2×10 -3 Below, 1×10 -3 Below, 9×10 -4 Below, 8×10 -4 Below or 7×10 -4 the following.

[0251] <(E) Free Radical Curing Resins>

[0252] The resin composition of the first embodiment of the present invention may optionally contain an (E) radical curable resin. The (E) radical curable resin may be used alone or in combination of two or more. By containing an (E) radical curable resin in the resin composition, the difference between the dielectric loss tangent (Df) at high temperature (100°C) and at room temperature (23°C) (temperature dependence of the dielectric loss tangent) can be reduced, and the glass transition temperature (Tg) of the cured product can be increased.

[0253] (E) Free radical curable resins may have olefinically unsaturated bonds. For example, (E) free radical curable resins may have unsaturated hydrocarbon groups such as vinyl, allyl, 3-cyclohexenyl, 3-cyclopentenyl, p-vinylphenyl, m-vinylphenyl, o-vinylphenyl; and free radical polymerizable groups such as α,β-unsaturated carbonyl groups such as acryloyl, methacryloyl, and maleimide (2,5-dihydro-2,5-dioxo-1H-pyrrole-1-yl). It is preferable to have unsaturated hydrocarbon groups or α,β-unsaturated carbonyl groups, and more preferably α,β-unsaturated carbonyl groups. Furthermore, (E) free radical curable resins preferably have two or more free radical polymerizable groups.

[0254] Examples of (E) radical-curable resins include (meth)acrylic acid-based radical-curable resins, styrene-based radical-curable resins, allyl-based radical-curable resins, and maleimide-based radical-curable resins. Styrene-based or maleimide-based radical-curable resins are preferred, and maleimide-based radical-curable resins are more preferred. The term "(meth)acrylic acid-based radical-curable resin" refers to a resin containing acryloyl or methacryloyl groups. By including a maleimide-based radical-curable resin in the resin composition, the difference between the dielectric loss tangent (Df) at high temperature (100°C) and at room temperature (23°C) can be reduced (the temperature dependence of the dielectric loss tangent). In addition, by including a styrene-based free radical curable resin in the resin composition, it is possible to further reduce the dielectric loss tangent of the cured product at room temperature (23°C) and high temperature (100°C), reduce the coefficient of linear expansion of the cured product, and increase the glass transition temperature of the cured product.

[0255] In the case of (meth)acrylic acid-based free radical curable resins, for example, it is a compound having one or more, preferably two or more, acryloyl groups and / or methacryloyl groups. Examples of low molecular weight (molecular weight less than 1000) aliphatic (meth)acrylate compounds, such as cyclohexane-1,4-diethanol di(meth)acrylate, cyclohexane-1,3-diethanol di(meth)acrylate, tricyclodecanediethanol di(meth)acrylate, neopentyl glycol di(meth)acrylate, 1,4-butanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,8-octanediol di(meth)acrylate, 1,9-nonanediol di(meth)acrylate, 1,10-decanediol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, trimethylolethane tri(meth)acrylate, glycerol tri(meth)acrylate, and pentaerythritol tetra(meth)acrylate; dioxanediol di(meth)acrylate, 3,6-dioxane-1,8-octanediol di(meth)acrylate, etc. Low molecular weight (molecular weight less than 1000) ether-containing (meth)acrylate compounds such as diol di(meth)acrylate, 3,6,9-trioxaundecane-1,11-diol di(meth)acrylate, polyethylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, 9,9-bis[4-(2-acryloyloxyethoxy)phenyl]fluorene, ethoxylated bisphenol A di(meth)acrylate, propoxylated bisphenol A di(meth)acrylate, etc.; low molecular weight (molecular weight less than 1000) isocyanurate-containing (meth)acrylate compounds such as tri(3-hydroxypropyl)isocyanurate tri(meth)acrylate, tri(2-hydroxyethyl)isocyanurate tri(meth)acrylate, ethoxylated isocyanuric acid tri(meth)acrylate, etc.; high molecular weight (molecular weight greater than 1000) acrylate compounds such as (meth)acrylate-modified polyphenylene ether resin, etc. Among these, as a (meth)acrylic acid-based free radical curable resin, a low molecular weight (molecular weight less than 1000) ether-containing (meth)acrylic acid ester compound is preferred, dioxanediol di(meth)acrylic acid ester is more preferred, and dioxanediol diacrylate is even more preferred.

[0256] Commercially available (meth)acrylic acid-based free radical curing resins include, for example, "A-DOG" (dioxanediol diacrylate) manufactured by Shin-Nakamura Chemical Industry Co., Ltd., "DCP-A" (tricyclodecanediethanol diacrylate) and "DCP" (tricyclodecanediethanol dimethacrylate) manufactured by Kyoeisha Chemical Co., Ltd., "KAYARAD R-684" (tricyclodecanediethanol diacrylate) and "KAYARAD R-604" (dioxanediol diacrylate) manufactured by Nippon Kayaku Co., Ltd., and "SA-9000" and "SA-9000-111" (methacrylic acid modified polyphenylene ether) manufactured by SABIC.

[0257] Styrene-based free radical curable resins are, for example, compounds having one or more, preferably two or more, vinyl groups directly bonded to aromatic carbon atoms. Examples of styrene-based free radical curable resins include low molecular weight (molecular weight less than 1000) styrene compounds such as divinylbenzene, 2,4-divinyltoluene, 2,6-divinylnaphthalene, 1,4-divinylnaphthalene, 4,4'-divinylbiphenyl, 1,2-bis(4-vinylphenyl)ethane, 2,2-bis(4-vinylphenyl)propane, and bis(4-vinylphenyl) ether; and high molecular weight (molecular weight 1000 or more) styrene compounds such as vinylbenzyl-modified polyphenylene ether resin and styrene-divinylbenzene copolymer. Among these, high molecular weight (molecular weight 1000 or more) styrene-based free radical curable resins are preferred, and vinylbenzyl-modified polyphenylene ether resins are more preferred.

[0258] Commercially available styrene-based free radical curable resins include, for example, "ODV-XET(X03)", "ODV-XET(X04)", and "ODV-XET(X05)" (styrene-divinylbenzene copolymer) manufactured by Nippon Steel Kemica & Materia, and "OPE-2St", "OPE-2St 1200", and "OPE-2St 2200" (vinyl benzyl modified polyphenylene ether resin) manufactured by Mitsubishi Gas Chemical Co., Ltd.

[0259] Allyl-based free radical curable resins are, for example, compounds having one or more, preferably two or more, allyl groups. Examples of allyl-based free radical curable resins include, for instance, allyl ester compounds of aromatic carboxylic acids such as diallyl biphenylate, triallyl trimellitate, diallyl phthalate, diallyl isophthalate, diallyl terephthalate, diallyl 2,6-naphthalenedicarboxylate, and diallyl 2,3-naphthalenedicarboxylate; allyl isocyanurate compounds such as 1,3,5-triallyl isocyanurate and 1,3-diallyl-5-glycidyl isocyanurate; and 2,2-bis[3-allyl-4-(glycidyl)-5 ... Aromatic allyl compounds containing epoxy, such as [[3-allyl-4-(3,4-dihydro-2H-1,3-benzoxazine-3-yl)phenyl]methane; aromatic allyl compounds containing benzoxazine, such as bis[3-allyl-4-(3,4-dihydro-2H-1,3-benzoxazine-3-yl)phenyl]methane; aromatic allyl compounds containing ether, such as 1,3,5-triallyl ether benzene; allyl silane compounds, such as diallyl diphenylsilane; and resins represented by the following formula (E-1) obtained by reacting o-allylphenol, dicyclopentadiene-phenol copolymer resin, and isophthaloyl chloride.

[0260]

Chemistry 16

[0261]

[0262] (In formula (E-1), the wavy line represents the structure obtained by the addition polymerization of isophthaloyl chloride and phenol with resin and / or o-allylphenol.)

[0263] Among these, allyl-based free radical curable resins are preferably aromatic carboxylic acid allyl ester compounds or resins represented by the above formula (E-1), and more preferably diallyl biphenyl ester or resins represented by the above formula (E-1).

[0264] Commercially available allyl-based free radical curable resins include, for example, "TAIC" (1,3,5-triallyl isocyanurate) manufactured by Nippon Chemical Co., Ltd., "DAD" (diallyl biphenyl dicarboxylate) manufactured by Nippon Technofenkemica Co., Ltd., "TRIAM-705" (triallyl trimellitate) manufactured by Fujifilm and Koujun Pharmaceutical Co., Ltd., and "DAND" (2,3-naphthalene) manufactured by Nippon Technofenkemica Co., Ltd. Diallyl dicarboxylate, ALP-d (bis[3-allyl-4-(3,4-dihydro-2H-1,3-benzoxazin-3-yl)phenyl]methane) manufactured by Shikoku Chemical Industries, RE-810NM (2,2-bis[3-allyl-4-(glycidoxy)phenyl]propane) manufactured by Nippon Kayaku Co., Ltd., DA-MGIC (1,3-diallyl-5-glycidyl isocyanurate) manufactured by Shikoku Chemical Industries, etc.

[0265] Maleimide-based free radical curable resins are, for example, compounds having one or more, preferably two or more, maleimide groups. Maleimide-based free radical curable resins can be aliphatic maleimide compounds containing an aliphatic amine skeleton, or aromatic maleimide compounds containing an aromatic amine skeleton. Commercially available maleimide-based free radical curable resins include, for example, Shin-Etsu Chemical Industry Co., Ltd.'s "SLK-2600", Designer Molecules Inc.'s "BMI-1500", "BMI-1700", "BMI-3000J", "BMI-689", and "BMI-2500" (maleimide resin containing a dimer diamine structure), Designer Molecules Inc.'s "BMI-6100" (aromatic maleimide resin), Nippon Kayaku Co., Ltd.'s "MIR-5000-60T" and "MIR-3000-70MT" (biphenyl aryl phenolic varnish type maleimide resin), Kei Ii Kasei Co., Ltd.'s "BMI-70" and "BMI-80", and Daiwa Kasei Corporation's "BMI-2300" and "BMI-TMH". Alternatively, the maleimide-based free radical curing resin disclosed in Patent Application Publication No. 2020-500211 (a maleimide resin containing an indane ring skeleton) can be used. Among these, maleimide resins containing a dimer diamine structure or biphenyl alkylphenol varnish-type maleimide resins are preferred as maleimide-based free radical curing resins.

[0266] (E) The olefin unsaturated bond equivalent of the free radical curable resin is preferably 20–3000 g / eq., more preferably 50–2500 g / eq., further preferably 70–2000 g / eq., and particularly preferably 90–1500 g / eq. The olefin unsaturated bond equivalent indicates the mass of the free radical curable resin per olefin unsaturated bond equivalent.

[0267] (E) The weight-average molecular weight (Mw) of the free radical curable resin is preferably 40,000 or less, more preferably 10,000 or less, even more preferably 5,000 or less, and particularly preferably 3,000 or less. There is no particular limitation on the lower limit, for example, it can be 150 or more.

[0268] When the resin composition of the first embodiment contains component (E), regarding the content of component (E), from the viewpoint of significantly obtaining the effects of the present invention, when the non-volatile component in the resin composition is set to 100% by mass, it is preferably 0.01% by mass or more or 0.02% by mass or more, more preferably 0.05% by mass or more, 0.08% by mass or more or 0.1% by mass or more, further preferably 0.2% by mass or more, 0.5% by mass or more or 0.8% by mass or more, and particularly preferably 1% by mass or more, 1.2% by mass or more or 1.4% by mass or more. The upper limit is preferably 20% by mass or less or 18% by mass or less, more preferably 15% by mass or less, 12% by mass or less or 10% by mass or less, further preferably 8% by mass or less, 5% by mass or less or 4% by mass or less, and particularly preferably 3% by mass or less, 2% by mass or less or 1.8% by mass or less.

[0269] When the resin composition of the first embodiment contains component (E), regarding the content of component (E), from the viewpoint of significantly obtaining the effects of the present invention, when the resin component in the resin composition is set to 100% by mass, it is preferably 0.02% by mass or more, 0.05% by mass or more, or 0.1% by mass or more, more preferably 0.2% by mass or more, 0.5% by mass or more, or 0.8% by mass or more, further preferably 1% by mass or more, 1.5% by mass or more, or 2% by mass or more, particularly preferably 2.5% by mass or more, 3% by mass or more, or 3.5% by mass or more. The upper limit is preferably 30% by mass or less or 25% by mass or less, more preferably 20% by mass or less, 15% by mass or less, or 10% by mass or less, further preferably 9% by mass or less, 8% by mass or less, or 7% by mass or less, particularly preferably 6% by mass or less, 5% by mass or less, or 4.5% by mass or less.

[0270] When the resin composition of the first embodiment contains component (E), the mass ratio of component (E) to component (A1) [(E) component / (A1) component] is preferably 0.01 or more, 0.02 or more, or 0.05 or more, more preferably 0.08 or more, 0.1 or more, or 0.2 or more, even more preferably 0.5 or more, 0.8 or more, or 1 or more, and particularly preferably 1.2 or more, 1.4 or more, or 1.6 or more, in terms of the mass ratio of component (E) to component (A1) [(E) component / (A1) component], from the viewpoints of significantly obtaining the effects of the present invention, reducing the coefficient of linear expansion of the cured product, and increasing the glass transition temperature of the cured product. The upper limit is preferably 100 or less or 80 or less, more preferably 50 or less, 20 or less, or 10 or less, even more preferably 8 or less, 5 or less, or 4 or less, and particularly preferably 3 or less, 2 or less, or 1.8 or less.

[0271] When the resin composition of the first embodiment contains component (A2) and component (E), from the viewpoint of significantly obtaining the effects of the present invention, the mass ratio of component (E) to component (A2) [(E) component / (A2) component] is preferably 0.0001 or more or 0.0005 or more, more preferably 0.001 or more, 0.002 or more or 0.005 or more, further preferably 0.008 or more, 0.01 or more or 0.02 or more, and particularly preferably 0.03 or more, 0.04 or more or 0.05 or more. The upper limit is preferably 5 or less or 2 or less, more preferably 1 or less or 0.8 or less, further preferably 0.5 or less, 0.2 or less or 0.1 or less, and particularly preferably 0.09 or less, 0.08 or less or 0.07 or less.

[0272] When the resin composition of the first embodiment contains component (E), from the viewpoint of significantly obtaining the effects of the present invention, the mass ratio of component (E) to component (A) [component (E) / component (A)] is preferably 0.0001 or more or 0.0005 or more, more preferably 0.001 or more, 0.002 or more or 0.005 or more, further preferably 0.008 or more, 0.01 or more or 0.02 or more, and particularly preferably 0.03 or more, 0.04 or more or 0.05 or more. The upper limit is preferably 5 or less or 2 or less, more preferably 1 or less or 0.8 or less, further preferably 0.5 or less, 0.2 or less or 0.1 or less, and particularly preferably 0.09 or less, 0.08 or less or 0.07 or less.

[0273] When the resin composition of the first embodiment contains component (E), from the viewpoint of significantly obtaining the effects of the present invention, the mass ratio of component (E) to component (B) [(E) component / (B) component] is preferably 0.001 or more, more preferably 0.005 or more, 0.008 or more, or 0.01 or more, further preferably 0.02 or more, 0.05 or more, or 0.08 or more, and particularly preferably 0.1 or more, 0.12 or more, or 0.14 or more. The upper limit is preferably 10 or less, 8 or less, or 5 or less, more preferably 2 or less, 1 or less, or 0.8 or less, further preferably 0.6 or less, 0.5 or less, or 0.4 or less, and particularly preferably 0.3 or less, 0.2 or less, or 0.18 or less.

[0274] When the resin composition of the first embodiment contains component (E), from the viewpoint of significantly obtaining the effects of the present invention, the mass ratio of component (E) to component (C) [component (E) / component (C)] is preferably 0.0001 or more, 0.0002 or more, or 0.0005 or more, more preferably 0.0008 or more, 0.001 or more, or 0.002 or more, even more preferably 0.005 or more, 0.008 or more, or 0.01 or more, and particularly preferably 0.015 or more, 0.02 or more, or 0.025 or more. In terms of the upper limit, from the viewpoint of further reducing the dielectric loss tangent of the cured material at room temperature (23°C) and high temperature (100°C) and from the viewpoint of reducing the linear expansion coefficient of the cured material, it is preferable to be 2 or less or 1 or less, more preferably 0.8 or less, 0.5 or less or 0.2 or less, even more preferably 0.1 or less, 0.08 or less or 0.06 or less, and particularly preferably 0.05 or less, 0.04 or less or 0.03 or less.

[0275] When the resin composition of the first embodiment contains component (E), from the viewpoint of significantly obtaining the effects of the present invention, the mass ratio of component (1D) to component (E) [(1D) component / (E) component] is preferably 0.0001 or more or 0.0005 or more, more preferably 0.001 or more or 0.002 or more, further preferably 0.005 or more, 0.008 or more or 0.01 or more, and particularly preferably 0.015 or more, 0.018 or more or 0.02 or more. The upper limit is preferably 2 or less or 1 or less, more preferably 0.8 or less, 0.5 or less or 0.2 or less, further preferably 0.1 or less, 0.08 or less or 0.06 or less, and particularly preferably 0.05 or less, 0.04 or less, 0.035 or less, 0.03 or less or 0.025 or less.

[0276] <(F) Curing Accelerator>

[0277] Regarding the resin composition of the first embodiment of the present invention, as an optional component, it may contain a curing accelerator (F), preferably a curing accelerator (F). The curing accelerator (F) functions as a curing catalyst that promotes the curing of cyclic ether compounds of four members or less (A) and / or curing agents (B).

[0278] Examples of (F) curing accelerators include phosphorus-based curing accelerators, urea-based curing accelerators, guanidine-based curing accelerators, imidazole-based curing accelerators, metal-based curing accelerators, and amine-based curing accelerators. A single (F) curing accelerator may be used, or two or more may be used in combination. Preferably, the (F) curing accelerator includes an amine-based curing accelerator or an imidazole-based curing accelerator, and more preferably, an amine-based curing accelerator.

[0279] Examples of amine-based curing accelerators include trialkylamines such as triethylamine and tributylamine; pyridines such as 4-dimethylaminopyridine; benzyl dimethylamine, 2,4,6-tris(dimethylaminomethyl)phenol, and 1,8-diazabicyclo(5,4,0)-undecene, with pyridines being preferred, and 4-dimethylaminopyridine being more preferred. These can be used individually or in combination of two or more.

[0280] As an amine-based curing accelerator, commercially available products can be used, such as "MY-25" manufactured by Ajinomoto Fintech Co., Ltd., and "DMAP" manufactured by Hiroei Chemical Co., Ltd.

[0281] Examples of phosphorus-based curing accelerators include, for instance, tetrabutylphosphonium bromide, tetrabutylphosphonium chloride, tetrabutylphosphonium acetate, tetrabutylphosphonium decanoate, tetrabutylphosphonium laurate, bis(tetrabutylphosphonium)pyromellitic phthalate, tetrabutylphosphonium hydrogen hexahydrophthalate, tetrabutylphosphonium 2,6-bis[(2-hydroxy-5-methylphenyl)methyl]-4-methylphenolate, and di-tert-butylmethylphosphonium tetraphenylborate, as well as aliphatic phosphonium salts such as methyltriphenylphosphonium bromide, ethyltriphenylphosphonium bromide, propyltriphenylphosphonium bromide, butyltriphenylphosphonium bromide, benzyltriphenylphosphonium chloride, tetraphenylphosphonium bromide, and p-tolyltriphenylphosphonium bromide. Aromatic phosphonium salts such as phosphonium tetra-p-tolylborate, tetraphenylphosphonium tetraphenylborate, tetraphenylphosphonium tetrap-tolylborate, triphenylethylphosphonium tetraphenylborate, tri(3-methylphenyl)ethylphosphonium tetraphenylborate, tri(2-methoxyphenyl)ethylphosphonium tetraphenylborate, (4-methylphenyl)triphenylphosphonium thiocyanate, tetraphenylphosphonium thiocyanate, and butyltriphenylphosphonium thiocyanate; aromatic phosphine-borane complexes such as triphenylphosphine-triphenylborane; aromatic phosphine-quinone addition reactants such as triphenylphosphine-p-benzoquinone addition reactants; tributylphosphine, tri-tert-butylphosphine, trioctylphosphine, and di-tert-butyl(2- Aliphatic phosphines such as butylene(3-methyl-2-butenyl)phosphine, di-tert-butyl(3-methyl-2-butenyl)phosphine, and tricyclohexylphosphine; dibutylphenylphosphine, di-tert-butylphenylphosphine, methyldiphenylphosphine, ethyldiphenylphosphine, butyldiphenylphosphine, diphenylcyclohexylphosphine, triphenylphosphine, tri-o-tolylphosphine, tri-m-tolylphosphine, tri-p-tolylphosphine, tri(4-ethylphenyl)phosphine, tri(4-propylphenyl)phosphine, tri(4-isopropylphenyl)phosphine, tri(4-butylphenyl)phosphine, tri(4-tert-butylphenyl)phosphine, tri(2,4-dimethylphenyl)phosphine, tri(2,5-dimethylphenyl)phosphine, tri(2,6-dimethylphenyl)phosphine, etc. Aromatic phosphines include tris(3,5-dimethylphenyl)phosphine, tris(2,4,6-trimethylphenyl)phosphine, tris(2,6-dimethyl-4-ethoxyphenyl)phosphine, tris(2-methoxyphenyl)phosphine, tris(4-methoxyphenyl)phosphine, tris(4-ethoxyphenyl)phosphine, tris(4-tert-butoxyphenyl)phosphine, diphenyl-2-pyridylphosphine, 1,2-bis(diphenylphosphino)ethane, 1,3-bis(diphenylphosphino)propane, 1,4-bis(diphenylphosphino)butane, 1,2-bis(diphenylphosphino)acetylene, and 2,2'-bis(diphenylphosphino)diphenyl ether. These can be used alone or in combination of two or more.

[0282] Examples of urea-based curing accelerators include, for instance, 1,1-dimethylurea; aliphatic dimethylureas such as 1,1,3-trimethylurea, 3-ethyl-1,1-dimethylurea, 3-cyclohexyl-1,1-dimethylurea, and 3-cyclooctyl-1,1-dimethylurea; 3-phenyl-1,1-dimethylurea, 3-(4-chlorophenyl)-1,1-dimethylurea, 3-(3,4-dichlorophenyl)-1,1-dimethylurea, 3-(3-chloro-4-methylphenyl)-1,1-dimethylurea, 3-(2-methylphenyl)-1,1-dimethylurea, 3-(4-methylphenyl)-1,1-dimethylurea, and 3-(3,4-dimethylphenyl)-1... Aromatic dimethylureas include 1-dimethylurea, 3-(4-isopropylphenyl)-1,1-dimethylurea, 3-(4-methoxyphenyl)-1,1-dimethylurea, 3-(4-nitrophenyl)-1,1-dimethylurea, 3-[4-(4-methoxyphenoxy)phenyl]-1,1-dimethylurea, 3-[4-(4-chlorophenoxy)phenyl]-1,1-dimethylurea, 3-[3-(trifluoromethyl)phenyl]-1,1-dimethylurea, N,N-(1,4-phenylene)bis(N',N'-dimethylurea), and N,N-(4-methyl-1,3-phenylene)bis(N',N'-dimethylurea)[toluenebisdimethylurea], etc. These can be used alone or in combination of two or more.

[0283] Examples of guanidine-based curing accelerators include dicyandiamide, 1-methylguanidine, 1-ethylguanidine, 1-cyclohexylguanidine, 1-phenylguanidine, 1-(o-tolyl)guanidine, dimethylguanidine, diphenylguanidine, trimethylguanidine, tetramethylguanidine, pentamethylguanidine, 1,5,7-triazabicyclo[4.4.0]dec-5-ene, 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene, 1-methylbiguanidine, 1-ethylbiguanidine, 1-n-butylbiguanidine, 1-n-octadecylbiguanidine, 1,1-dimethylbiguanidine, 1,1-diethylbiguanidine, 1-cyclohexylbiguanidine, 1-allylbiguanidine, 1-phenylbiguanidine, and 1-(o-tolyl)biguanidine. These can be used individually or in combination of two or more.

[0284] Examples of imidazole-based curing accelerators include 2-methylimidazolium, 2-undecylimidazolium, 2-heptadecylimidazolium, 1,2-dimethylimidazolium, 2-ethyl-4-methylimidazolium, 2-phenylimidazolium, 2-phenyl-4-methylimidazolium, 1-benzyl-2-methylimidazolium, 1-benzyl-2-phenylimidazolium, 1-cyanoethyl-2-methylimidazolium, 1-cyanoethyl-2-undecylimidazolium, 1-cyanoethyl-2-ethyl-4-methylimidazolium, 1-cyanoethyl-2-phenylimidazolium, 1-cyanoethyl-2-undecylimidazolium trimellitate, 1-cyanoethyl-2-phenylimidazolium trimellitate, 2,4-diamino-6-[2'-methylimidazolyl-(1')]-ethyl-triazine, and 2,4-diamino-6-[2'-methylimidazolyl-(1')]-ethyl-triazine. -[2'-undecylimidazolyl-(1')]-ethyl-triazine, 2,4-diamino-6-[2'-ethyl-4'-methylimidazolyl-(1')]-ethyl-triazine, 2,4-diamino-6-[2'-methylimidazolyl-(1')]-ethyl-triazine isocyanuric acid adduct, 2-phenylimidazolyl isocyanuric acid adduct, 2-phenyl-4,5-dihydroxymethylimidazolium, 2-phenyl-4-methyl-5-hydroxymethylimidazolium, 2,3-dihydro-1H-pyrrolo[1,2-a]benzimidazole, 1-dodecyl-2-methyl-3-benzylimidazolium chloride, 2-methylimidazoline, 2-phenylimidazoline and other imidazole compounds and adducts of imidazole compounds with epoxy resins, preferably 1-benzyl-2-phenylimidazolium.

[0285] Commercially available imidazole-based curing accelerators include, for example, those manufactured by Shikoku Chemical Industry Co., Ltd. such as "1B2PZ", "2E4MZ", "2MZA-PW", "2MZ-OK", "2MA-OK", "2MA-OK-PW", "2P4MZ", "2PHZ", "2PHZ-PW", "Cl 1Z", "Cl 1Z-CN", "Cl 1Z-CNS", and "C11Z-A"; and "P200-H50" manufactured by Mitsubishi Chemical Co., Ltd. These can be used individually or in combination of two or more.

[0286] Examples of metal-based curing accelerators include organometallic complexes or organometallic salts of metals such as cobalt, copper, zinc, iron, nickel, manganese, and tin. Specific examples of organometallic complexes include cobalt(II) acetylacetone, cobalt(III) acetylacetone, copper(II) acetylacetone, zinc(II) acetylacetone, iron(III) acetylacetone, nickel(II) acetylacetone, and manganese(II) acetylacetone. Examples of organometallic salts include zinc octoate, tin octoate, zinc naphthenate, cobalt naphthenate, tin stearate, and zinc stearate. These can be used individually or in combination of two or more.

[0287] When the resin composition of the first embodiment contains component (F), regarding the content of component (F), from the viewpoint of significantly obtaining the effects of the present invention, when the non-volatile component in the resin composition is set to 100% by mass, it is preferably 0.001% by mass or more or 0.002% by mass or more, more preferably 0.005% by mass or more or 0.008% by mass or more, further preferably 0.01% by mass or more, 0.02% by mass or more or 0.05% by mass or more, particularly preferably 0.06% by mass or more, 0.08% by mass or more or 0.09% by mass or more. The upper limit is preferably 10% by mass or less or 8% by mass or less, more preferably 5% by mass or less, 2% by mass or less or 1% by mass or less, further preferably 0.8% by mass or less, 0.5% by mass or less or 0.4% by mass or less, particularly preferably 0.3% by mass or less, 0.2% by mass or less or 0.15% by mass or less.

[0288] When the resin composition of the first embodiment contains component (F), regarding the content of component (F), from the viewpoint of significantly obtaining the effects of the present invention, when the resin component in the resin composition is set to 100% by mass, it is preferably 0.002% by mass or more, 0.005% by mass or more, or 0.008% by mass or more, more preferably 0.01% by mass or more, 0.02% by mass or more, or 0.05% by mass or more, further preferably 0.08% by mass or more, 0.1% by mass or more, or 0.12% by mass or more, particularly preferably 0.15% by mass or more, 0.2% by mass or more, or 0.22% by mass or more. The upper limit is preferably 20% by mass or less, 10% by mass or less, or 8% by mass or less, more preferably 5% by mass or less, 2% by mass or less, or 1% by mass or less, further preferably 0.8% by mass or less, 0.6% by mass or less, or 0.5% by mass or less, particularly preferably 0.4% by mass or less, 0.3% by mass or less, or 0.25% by mass or less.

[0289] When the resin composition of the first embodiment contains component (F), the mass ratio of component (F) to component (A1) [(F) component / (A1) component] is preferably 0.001 or more, more preferably 0.002 or more or 0.005 or more, further preferably 0.008 or more or 0.01 or more, and particularly preferably 0.015 or more or 0.02 or more, in one embodiment, it may be 0.03 or more, 0.05 or more, 0.08 or more, 0.09 or more, etc. The upper limit is preferably 5 or less, more preferably 2 or less or 1 or less, further preferably 0.8 or less or 0.6 or less, and particularly preferably 0.5 or less or 0.45 or less, etc. In another embodiment, it may be 0.4 or less, 0.3 or less, 0.2 or less, 0.15 or less, etc.

[0290] In the case where the resin composition of the first embodiment contains component (A2) and component (F), from the viewpoint of significantly obtaining the effects of the present invention, the mass ratio of component (F) to component (A2) [component (F) / (A2)] is preferably 1×10⁻⁶. -5 Above or 5×10 -5 The above is preferred to be 1×10 -4 Above or 2×10 -4 The above is further optimized to be 5×10 -4 Above or 8×10 -4 The above is particularly preferred, with 1×10 -3 Above, 2×10 -3 Above or 3×10 -3 The above. The upper limit is preferably below 1 or 5 × 10. -1 Hereinafter, 1×10 is more preferred. -1 Below or 8×10 -2 The following is a further preferred option: 5×10 -2 Below or 2×10 -2 The following is particularly preferred: 1×10 -2 Below, 8×10 -3 Below or 7×10 -3 The following. Additionally, in one embodiment, it can be 6 × 10. -3 Below, 5×10 -3 Below, 4×10 -3 The following, etc.

[0291] In the case where the resin composition of the first embodiment contains component (F), from the viewpoint of significantly obtaining the effects of the present invention, the mass ratio of component (F) to component (A) [component (F) / component (A)] is preferably 1×10⁻⁶.-5 Above or 5×10 -5 The above is preferred to be 1×10 -4 Above or 2×10 -4 The above is further optimized to be 5×10 -4 Above or 8×10 -4 The above is particularly preferred, with 1×10 -3 Above, 2×10 -3 Above or 3×10 -3 The above. The upper limit is preferably below 1 or 5 × 10. -1 Hereinafter, 1×10 is more preferred. -1 Below or 8×10 -2 The following is a further preferred option: 5×10 -2 Below, 2×10 -2 Below or 1×10 -2 The following is particularly preferred: 8×10 -3 Below, 5×10 -3 Below or 4×10 -3 the following.

[0292] In the case where the resin composition of the first embodiment contains component (F), from the viewpoint of significantly obtaining the effects of the present invention, the mass ratio of component (F) to component (B) [component (F) / component (B)] is preferably 1×10⁻⁶. -5 Above or 5×10 -5 The above is preferred to be 1×10 -4 Above, 2×10 -4 Above or 5×10 -4 The above is further optimized to 8×10 -4 Above, 1×10 -3 Above or 2×10 -3 The above is particularly preferred, with 3×10 -3 Above, 5×10 -3 Above or 7×10 -3 Above. Preferably, it is 1 or less or 8 × 10. -1 The following is more preferably 5×10 -1 Below or 2×10 -1 Hereinafter, 1×10 is further preferred. -1 Below or 8×10 -2 The following is particularly preferred: 5×10 -2 Below, 2×10 -2 Below or 1.5×10 -2 The following. Additionally, in one embodiment, it can be 1×10. -2 Below, 9×10 -3 Below, 8×10 -3 The following, etc.

[0293] In the case where the resin composition of the first embodiment contains component (F), from the viewpoint of significantly obtaining the effects of the present invention, the mass ratio of component (F) to component (C) [component (F) / component (C)] is preferably 1×10⁻⁶. -5 Above or 2×10 -5 The above is preferred, with 5×10 being more ideal. -4 Above or 8×10 -5 The above is further preferred to be 1×10 -4 Above or 2×10 -4 The above is particularly preferred, with 5×10 -4 Above or 8×10 -4 That's all. Additionally, in one embodiment, it can be 9×10. -4 Above, 1×10 -3 Above, 1.2×10 -3 Above, 1.5×10 -3 The above, etc. Regarding the upper limit, from the viewpoint of further reducing the dielectric loss tangent of the cured material at room temperature (23°C) and high temperature (100°C), and from the viewpoint of reducing the linear expansion coefficient of the cured material, it is preferable to have 1 or less and 5 × 10⁻⁶. -1 Below or 1×10 -1 The following is more preferably 8×10 -2 Below, 5×10 -2 Below or 2×10 -2 Hereinafter, 1×10 is further preferred. -2 Below, 8×10 -3 Below or 5×10 -3 The following is particularly preferred: 3×10 -3 Below, 2×10 -3 Below or 1.8×10 -3 the following.

[0294] When the resin composition of the first embodiment contains component (F), from the viewpoint of significantly obtaining the effects of the present invention, the mass ratio of component (1D) to component (F) [(1D) component / (F) component] is preferably 0.001 or more, more preferably 0.01 or more or 0.02 or more, further preferably 0.05 or more or 0.08 or more, and particularly preferably 0.1 or more or 0.15 or more. In another embodiment, it may be 0.2 or more, 0.3 or more, 0.35 or more, etc. The upper limit is preferably 50 or less or 20 or less, more preferably 10 or less or 8 or less, further preferably 5 or less, 2 or less or 1 or less, and particularly preferably 0.8 or less, 0.7 or less, 0.6 or less, 0.5 or less or 0.4 or less.

[0295] When the resin composition of the first embodiment contains component (E) and component (F), from the viewpoint of significantly obtaining the effects of the present invention, the mass ratio of component (F) to component (E) [component (F) / (E)] is preferably 0.0001 or more or 0.0005 or more, more preferably 0.001 or more, 0.002 or more or 0.005 or more, further preferably 0.008 or more, 0.01 or more or 0.02 or more, and particularly preferably 0.03 or more, 0.04 or more or 0.05 or more. The upper limit is preferably 5 or less or 2 or less, more preferably 1 or less or 0.8 or less, further preferably 0.5 or less, 0.2 or less or 0.1 or less, and particularly preferably 0.09 or less, 0.08 or less or 0.07 or less.

[0296] <(G) Organic filler materials>

[0297] The resin composition of the first embodiment of the present invention may optionally contain an organic filler (G). The organic filler (G) may be used alone or in combination of two or more. Furthermore, the resin composition of the first embodiment preferably contains at least one of the organic filler (G) and the thermoplastic resin (H) described later.

[0298] (G) The organic filler material exists in the resin composition in a particulate form. Examples of (G) organic filler materials include rubber particles, polyamide microparticles, silicone particles, core-shell particles, etc. In this invention, from the viewpoint of significantly obtaining the desired effects of the invention, the (G) organic filler material preferably includes either rubber particles or core-shell particles, more preferably rubber particles, and even more preferably core-shell rubber particles.

[0299] Examples of rubber components contained in rubber particles include olefin-based thermoplastic elastomers such as polybutadiene, polyisoprene, polychloroprene, 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 poly(meth)acrylate, poly(meth)acrylate, poly(cyclohexyl methacrylate), and poly(octyl methacrylate), with acrylic-based thermoplastic elastomers being preferred. Rubber particles containing acrylic-based thermoplastic elastomers as rubber components are called "acrylic-based rubber particles." Core-shell particles containing acrylic-based thermoplastic elastomers as rubber components are called "acrylic-based core-shell particles." Core-shell rubber particles containing acrylic thermoplastic elastomers as rubber components are referred to as "acrylic core-shell rubber particles". That is, (G) the organic filler material preferably contains either acrylic rubber particles or acrylic core-shell particles, more preferably acrylic rubber particles, and even more preferably acrylic core-shell rubber particles. Furthermore, silicone rubbers such as polysiloxane rubber can be mixed into the rubber component. The rubber component contained in the rubber particles preferably has a glass transition temperature of 0°C or below, more preferably -10°C or below, even more preferably -20°C or below, and particularly preferably -30°C or below.

[0300] Commercially available products can be used as rubber particles, such as "EXL2655" manufactured by Ikudo Chemical Nippon Co., Ltd., and "Staffiroid AC3401N" and "Staffiroid AC3816N" manufactured by Iika Kogyo Co., Ltd. "Staffiroid AC3816N" is also equivalent to core-shell rubber particles.

[0301] Core-shell particles are particle-shaped organic filler materials having a core containing the rubber components listed above and a shell covering it with one or more layers. In one embodiment, core-shell particles are preferably particle-shaped organic filler materials consisting of a core containing the rubber components listed above and a shell covering it with one or more layers. Furthermore, core-shell particles are preferably core-shell graft copolymer particles having a core containing the rubber components listed above and a shell having a shell composed of monomers that can copolymerize with the rubber components contained in the core particles. In another embodiment, core-shell particles are more preferably core-shell graft copolymer particles consisting of a core containing the rubber components listed above and a shell composed of monomers that can copolymerize with the rubber components contained in the core particles. The term "core-shell" here does not necessarily mean that the core and shell can be clearly distinguished; it also includes cases where the boundary between the core and shell is unclear, and the core may not be completely covered by the shell.

[0302] The rubber component preferably contains 40% by mass or more in the core-shell graft copolymer particles, more preferably 50% by mass or more, and even more preferably 60% by mass or more. There is no particular upper limit to the content of the rubber component in the core-shell graft copolymer particles, but from the viewpoint of sufficiently covering the core particles with the shell, it is preferably 95% by mass or less, or 90% by mass or less.

[0303] As monomeric components forming the shell portion of core-shell graft copolymer particles, examples include (meth)acrylates such as methyl methacrylate, ethyl methacrylate, butyl methacrylate, cyclohexyl methacrylate, octyl methacrylate, and glycidyl methacrylate; (meth)acrylic acid; N-substituted maleimides such as N-methylmaleimide and N-phenylmaleimide; maleimides; α,β-unsaturated carboxylic acids such as maleic acid and itaconic acid; aromatic vinyl compounds such as styrene, 4-vinyltoluene, and α-methylstyrene; and (meth)acrylonitrile, with (meth)acrylates being preferred and methyl methacrylate being more preferred.

[0304] Commercially available products as core-shell graft copolymer particles include, for example, "CHT" manufactured by Samson SDI; "B602" manufactured by Techno UMG; and "Pararoide EXL2602", "Pararoide EXL2603", "Pararoide EXL2655", "Pararoide EXL2311", "Pararoide EXL2313", "Pararoide EXL2315", "Pararoide KM330", and "Pararoide EXL2602" manufactured by Michi Chemical Nippon Co., Ltd. "ロイドKM336P", "パラロイドKCZ201"; "メタブレンC-223A", "メ" manufactured by Mitsubishi Chemical Corporation "メタブレンE-901", "メタブレンS-2001", "メタブレンW-450A", "メタブレンSRK- 200"; "Kunka M-511", "Kunka M-600", and "Kunka M-400" manufactured by Kaneka Corporation , "カネエースM-580", "カネエースMR-01", etc. These can be used individually or in combination of 2 or more types.

[0305] The average particle size (average primary particle size) of the core-shell graft copolymer particles is not particularly limited, but is preferably 20 nm or more, more preferably 50 nm or more, further preferably 80 nm or more, and particularly preferably 100 nm or more. The upper limit is preferably 5000 nm or less, more preferably 2000 nm or less, further preferably 1000 nm or less, and particularly preferably 500 nm or less. The average particle size (average primary particle size) of the core-shell graft copolymer particles can be measured using a zeta potential particle size distribution measuring device or the like.

[0306] When the resin composition of the first embodiment contains component (G), regarding the content of component (G), from the viewpoint of significantly obtaining the effects of the present invention, when the non-volatile component in the resin composition is set to 100% by mass, it is preferably 0.001% by mass or more or 0.005% by mass or more, more preferably 0.01% by mass or more or 0.02% by mass or more, further preferably 0.05% by mass or more, 0.08% by mass or more or 0.1% by mass or more, and particularly preferably 0.2% by mass or more, 0.5% by mass or more or 0.7% by mass or more. The upper limit is preferably 20% by mass or less or 15% by mass or less, more preferably 10% by mass or less, 8% by mass or less or 6% by mass or less, further preferably 5% by mass or less, 4% by mass or less or 3% by mass or less, and particularly preferably 2% by mass or less, 1.5% by mass or less or 1% by mass or less.

[0307] When the resin composition of the first embodiment contains component (G), regarding the content of component (G), from the viewpoint of significantly obtaining the effects of the present invention, when the resin component in the resin composition is set to 100% by mass, it is preferably 0.01% by mass or more, 0.02% by mass or more, or 0.05% by mass or more, more preferably 0.08% by mass or more, 0.1% by mass or more, or 0.2% by mass or more, further preferably 0.5% by mass or more, 0.8% by mass or more, or 1% by mass or more, particularly preferably 1.5% by mass or more, 2% by mass or more, or 2.5% by mass or more. The upper limit is preferably 30% by mass or less or 25% by mass or less, more preferably 20% by mass or less or 15% by mass or less, further preferably 10% by mass or less, 8% by mass or less, or 6% by mass or less, particularly preferably 5% by mass or less, 4% by mass or less, or 3% by mass or less.

[0308] When the resin composition of the first embodiment contains component (G), the mass ratio of component (G) to component (A1) [(G) component / (A1) component] is preferably 0.01 or more, more preferably 0.05 or more or 0.08 or more, and even more preferably 0.1 or more or 0.2 or more, particularly preferably 0.5 or more, 0.8 or more, or 0.9 or more, from the viewpoints of significantly obtaining the effects of the present invention, reducing the coefficient of linear expansion of the cured product, and increasing the glass transition temperature of the cured product. The upper limit is preferably 100 or less or 80 or less, more preferably 50 or less or 20 or less, even more preferably 10 or less, 8 or less, or 5 or less, and particularly preferably 2 or less, 1.5 or less, or 1.2 or less, in terms of the mass ratio of component (G) to component (A1) [(G) component / (A1) component]

[0309] When the resin composition of the first embodiment contains components (A2) and (G), from the viewpoint of significantly obtaining the effects of the present invention, the mass ratio of component (G) to component (A2) [(G) component / (A2) component] is preferably 0.0001 or more or 0.0005 or more, more preferably 0.001 or more or 0.002 or more, further preferably 0.005 or more, 0.008 or more or 0.01 or more, and particularly preferably 0.02 or more, 0.03 or more or 0.04 or more. The upper limit is preferably 5 or less or 2 or less, more preferably 1 or less or 0.8 or less, further preferably 0.5 or less, 0.2 or less or 0.1 or less, and particularly preferably 0.08 or less, 0.06 or less or 0.05 or less.

[0310] When the resin composition of the first embodiment contains component (G), from the viewpoint of significantly obtaining the effects of the present invention, the mass ratio of component (G) to component (A) [(G) component / (A) component] is preferably 0.0001 or more or 0.0005 or more, more preferably 0.001 or more or 0.002 or more, further preferably 0.005 or more, 0.008 or more or 0.01 or more, and particularly preferably 0.02 or more, 0.03 or more or 0.04 or more. The upper limit is preferably 5 or less or 2 or less, more preferably 1 or less or 0.8 or less, further preferably 0.5 or less, 0.2 or less or 0.1 or less, and particularly preferably 0.08 or less, 0.06 or less or 0.05 or less.

[0311] When the resin composition of the first embodiment contains component (G), from the viewpoint of significantly obtaining the effects of the present invention, the mass ratio of component (G) to component (B) [(G) component / (B) component] is preferably 0.001 or more, more preferably 0.005 or more or 0.008 or more, further preferably 0.01 or more, 0.02 or more, or 0.04 or more, and particularly preferably 0.05 or more, 0.07 or more, or 0.08 or more. The upper limit is preferably 10 or less or 8 or less, more preferably 5 or less or 2 or less, further preferably 1 or less, 0.8 or less, or 0.5 or less, and particularly preferably 0.3 or less, 0.2 or less, or 0.1 or less.

[0312] When the resin composition of the first embodiment contains component (G), from the viewpoint of significantly obtaining the effects of the present invention, the mass ratio of component (G) to component (C) [(G) component / (C) component] is preferably 0.0001 or more or 0.0002 or more, more preferably 0.0005 or more or 0.0008 or more, further preferably 0.001 or more or 0.002 or more, and particularly preferably 0.005 or more, 0.008 or more or 0.01 or more. Regarding the upper limit, from the viewpoint of further reducing the dielectric loss tangent of the cured product at room temperature (23°C) and high temperature (100°C), and from the viewpoint of reducing the coefficient of linear expansion of the cured product, it is preferably 1 or less, 0.8 or less or 0.5 or less, more preferably 0.2 or less, 0.1 or less or 0.08 or less, further preferably 0.06 or less, 0.05 or less or 0.04 or less, and particularly preferably 0.03 or less, 0.02 or less or 0.015 or less.

[0313] When the resin composition of the first embodiment contains component (G), from the viewpoint of significantly obtaining the effects of the present invention, the mass ratio of component (1D) to component (G) [(1D) component / (G) component] is preferably 0.0001 or more or 0.0005 or more, more preferably 0.001 or more or 0.002 or more, further preferably 0.005 or more, 0.008 or more or 0.01 or more, and particularly preferably 0.02 or more, 0.03 or more or 0.04 or more. The upper limit is preferably 5 or less or 2 or less, more preferably 1 or less or 0.8 or less, further preferably 0.5 or less, 0.2 or less or 0.1 or less, and particularly preferably 0.08 or less, 0.07 or less or 0.06 or less.

[0314] When the resin composition of the first embodiment contains component (F) and component (G), from the viewpoint of significantly obtaining the effects of the present invention, the mass ratio of component (F) to component (G) [component (F) / component (G)] is preferably 0.001 or more or 0.002 or more, more preferably 0.005 or more, 0.008 or more or 0.01 or more, further preferably 0.02 or more, 0.05 or more or 0.08 or more, and particularly preferably 0.1 or more, 0.15 or more or 0.18 or more. The upper limit is preferably 20 or less or 10 or less, more preferably 8 or less or 5 or less, further preferably 2 or less, 1 or less or 0.8 or less, and particularly preferably 0.5 or less, 0.4 or less or 0.3 or less.

[0315] <(H) Thermoplastic Resin>

[0316] The resin composition of the first embodiment of the present invention may optionally contain a (H) thermoplastic resin. The (H) thermoplastic resin may be used alone or in combination of two or more. Furthermore, the resin composition of the first embodiment preferably contains at least one of the (G) organic filler material and the (H) thermoplastic resin described above.

[0317] Examples of thermoplastic resins include phenoxy resins, polyvinyl acetal resins, polyolefin resins, polybutadiene resins, polyimide resins, polyamide-imide resins, polyether-imide resins, polysulfone resins, polyethersulfone resins, polyphenylene ether resins, polycarbonate resins, polyetheretherketone resins, and polyester resins. Among these, phenoxy resins are preferred from the viewpoint of significantly obtaining the effects of the present invention. The phenoxy resins described herein are components other than those equivalent to epoxy resins. Furthermore, a single thermoplastic resin may be used, or two or more may be used in combination.

[0318] Examples of phenoxy resins include those having one or more skeletons selected from the following: bisphenol A skeleton, bisphenol F skeleton, bisphenol S skeleton, bisphenol acetophenone skeleton, phenolic varnish skeleton, biphenyl skeleton, fluorene skeleton, dicyclopentadiene skeleton, norbornene skeleton, naphthalene skeleton, anthracene skeleton, adamantane skeleton, terpene skeleton, and trimethylcyclohexane skeleton. The terminal group of the phenoxy resin can be any functional group such as a phenolic hydroxyl group or an epoxy group.

[0319] Specific examples of phenoxy resins include Mitsubishi Chemical's "1256" and "4250" (both phenoxy resins containing a bisphenol A backbone); Mitsubishi Chemical's "YX8100" (a phenoxy resin containing a bisphenol S backbone); Mitsubishi Chemical's "YX6954" (a phenoxy resin containing a bisphenol acetophenone backbone); Nippon Steel Kemica & Materia's "FX280" and "FX293"; and Mitsubishi Chemical's "YL6954BH30", "YL7500BH30", "YX6954BH30", "YX7553", "YX7553BH30", "YL7769BH30", "YL6794", "YL7213", "YL7290", "YL7482", and "YL7891BH30", etc.

[0320] Examples of polyvinyl acetal resins include polyvinyl formal resin and polyvinyl butyral resin, with polyvinyl butyral resin being preferred. Specific examples of polyvinyl acetal resins include the E-Lex BH series, BX series (e.g., BX-5Z), KS series (e.g., KS-1), BL series, and BM series manufactured by Sekisui Chemicals Co., Ltd.

[0321] Examples of polyolefin resins include, for instance, low-density polyethylene, ultra-low-density polyethylene, high-density polyethylene, ethylene-vinyl acetate copolymer, ethylene-ethyl acrylate copolymer, ethylene-methyl acrylate copolymer, and other ethylene-based copolymers; as well as polyolefin polymers such as polypropylene and ethylene-propylene block copolymers.

[0322] Specific examples of polyimide resins include "Rikakoto SN20" and "Rikakoto PN20" manufactured by Shin Nippon Rikka Co., Ltd.

[0323] Specific examples of polyamide-imide resins include "Viromax HR11NN" and "Viromax HR16NN" manufactured by Toyobo Co., Ltd. Specific examples of polyamide-imide resins include modified polyamide-imides such as "KS9100" and "KS9300" (polyamide-imide containing a polysiloxane backbone) manufactured by Resonack Co., Ltd.

[0324] Specific examples of polyethersulfone resins include "PES5003P" manufactured by Sumitomo Chemical Co., Ltd.

[0325] Specific examples of polysulfone resins include polysulfones such as "P1700" and "P3500" manufactured by Solbey Advanto Polymers Co., Ltd.

[0326] Examples of polyester resins include polyethylene terephthalate resin, polyethylene naphthalate resin, polybutylene terephthalate resin, polybutylene naphthalate resin, 1,3-propanediol terephthalate resin, 1,3-propanediol naphthalate resin, and polycyclohexanediol terephthalate resin.

[0327] Regarding the weight-average molecular weight (Mw) of the thermoplastic resin, from the viewpoint of significantly obtaining the effects of the present invention, it is preferably 8,000 or more, more preferably 10,000 or more, particularly preferably 20,000 or more, preferably 70,000 or less, more preferably 60,000 or less, and particularly preferably 50,000 or less.

[0328] When the resin composition of the first embodiment contains component (H), regarding the content of component (H), from the viewpoint of significantly obtaining the effects of the present invention, when the non-volatile component in the resin composition is set to 100% by mass, it is preferably 0.005% by mass, 0.01% by mass or more, or 0.02% by mass or more, more preferably 0.05% by mass or more, or 0.08% by mass or more, further preferably 0.1% by mass or more, or 0.2% by mass or more, particularly preferably 0.5% by mass or more, 0.8% by mass or more, or 1% by mass or more. The upper limit is preferably 20% by mass or less or 15% by mass or less, more preferably 10% by mass or less, 8% by mass or less, or 6% by mass or less, further preferably 5% by mass or less, 4% by mass or less, or 3% by mass or less, particularly preferably 2% by mass or less, 1.5% by mass or less, or 1.2% by mass or less.

[0329] When the resin composition of the first embodiment contains component (H), regarding the content of component (H), from the viewpoint of significantly obtaining the effects of the present invention, when the resin component in the resin composition is set to 100% by mass, it is preferably 0.01% by mass or more, 0.02% by mass or more, or 0.05% by mass or more, more preferably 0.08% by mass or more, 0.1% by mass or more, or 0.2% by mass or more, further preferably 0.5% by mass or more, 0.8% by mass or more, or 1% by mass or more, particularly preferably 1.5% by mass or more, 2% by mass or more, or 2.5% by mass or more. The upper limit is preferably 30% by mass or less or 25% by mass or less, more preferably 20% by mass or less or 15% by mass or less, further preferably 10% by mass or less, 8% by mass or less, or 6% by mass or less, particularly preferably 5% by mass or less, 4% by mass or less, or 3% by mass or less.

[0330] When the resin composition of the first embodiment contains the (H) component, the mass ratio of the (H) component to the (Al) component [(H) component / (Al) component] is preferably 0.001 or more or 0.005 or more, more preferably 0.01 or more or 0.02 or more, further preferably 0.05 or more or 0.08 or more, and particularly preferably 0.1 or more, 0.15 or more, or 0.2 or more, in one embodiment, it may be 0.3 or more, 0.4 or more, 0.5 or more, 0.6 or more, 0.7 or more, 0.8 or more, 0.9 or more, 1 or more, 1.1 or more, etc. The upper limit is preferably 100 or less, 80 or less, or 50 or less, more preferably 20 or less, 10 or less, or 8 or less, further preferably 5 or less, 4 or less, or 3 or less, and particularly preferably 2 or less, 1.5 or less, or 1.3 or less.

[0331] When the resin composition of the first embodiment contains both (A2) and (H) components, from the viewpoint of significantly obtaining the effects of the present invention, the mass ratio of (H) component to (A2) component [(H) component / (A2) component] is preferably 0.0001 or more or 0.0005 or more, more preferably 0.001 or more or 0.002 or more, further preferably 0.005 or more, 0.008 or more or 0.01 or more, and particularly preferably 0.02 or more, 0.03 or more or 0.04 or more. The upper limit is preferably 5 or less or 2 or less, more preferably 1 or less or 0.8 or less, further preferably 0.5 or less, 0.2 or less or 0.1 or less, and particularly preferably 0.08 or less, 0.06 or less or 0.055 or less. In one embodiment, it may be 0.05 or less, 0.045 or less, etc.

[0332] When the resin composition of the first embodiment contains component (H), from the viewpoint of significantly obtaining the effects of the present invention, the mass ratio of component (H) to component (A) [(H) component / (A) component] is preferably 0.0001 or more or 0.0005 or more, more preferably 0.001 or more or 0.002 or more, further preferably 0.005 or more, 0.008 or more or 0.01 or more, and particularly preferably 0.02 or more, 0.03 or more or 0.04 or more. The upper limit is preferably 5 or less or 2 or less, more preferably 1 or less or 0.8 or less, further preferably 0.5 or less, 0.2 or less or 0.1 or less, and particularly preferably 0.08 or less, 0.06 or less or 0.05 or less.

[0333] When the resin composition of the first embodiment contains component (H), from the viewpoint of significantly obtaining the effects of the present invention, the mass ratio of component (H) to component (B) [(H) component / (B) component] is preferably 0.001 or more, more preferably 0.005 or more or 0.008 or more, further preferably 0.01 or more, 0.02 or more, or 0.04 or more, and particularly preferably 0.05 or more, 0.07 or more, 0.08 or more, or 0.09 or more. The upper limit is preferably 10 or less or 8 or less, more preferably 5 or less or 2 or less, further preferably 1 or less, 0.8 or less, or 0.5 or less, and particularly preferably 0.3 or less, 0.2 or less, or 0.15 or less. In one embodiment, it may be 0.1 or less, etc.

[0334] When the resin composition of the first embodiment contains the (H) component, from the viewpoint of significantly obtaining the effects of the present invention, the mass ratio of the (H) component to the (C) component [(H) component / (C) component] is preferably 0.0001 or more or 0.0002 or more, more preferably 0.0005 or more or 0.0008 or more, further preferably 0.001 or more or 0.002 or more, and particularly preferably 0.005 or more, 0.008 or more, or 0.01 or more. In another embodiment, it may be 0.012 or more, 0.015 or more, 0.018 or more, etc. In terms of the upper limit, from the viewpoint of further reducing the dielectric loss tangent of the cured material at room temperature (23°C) and high temperature (100°C) and from the viewpoint of reducing the linear expansion coefficient of the cured material, it is preferable to be 1 or less, 0.8 or less, or 0.5 or less, more preferably 0.2 or less, 0.1 or less, or 0.08 or less, even more preferably 0.06 or less, 0.05 or less, or 0.04 or less, and particularly preferably 0.03 or less, or 0.02 or less.

[0335] When the resin composition of the first embodiment contains the (H) component, from the viewpoint of significantly obtaining the effects of the present invention, the mass ratio of the (1D) component to the (H) component [(1D) component / (H) component] is preferably 0.0001 or more or 0.0005 or more, more preferably 0.001 or more or 0.002 or more, further preferably 0.005 or more, 0.008 or more or 0.01 or more, and particularly preferably 0.02 or more, 0.025 or more or 0.03 or more. The upper limit is preferably 5 or less or 2 or less, more preferably 1 or less or 0.8 or less, further preferably 0.5 or less, 0.2 or less or 0.1 or less, and particularly preferably 0.08 or less, 0.06 or less, 0.05 or less or 0.04 or less.

[0336] When the resin composition of the first embodiment contains both component (E) and component (H), from the viewpoint of significantly obtaining the effects of the present invention, the mass ratio of component (H) to component (E) [(H) component / (E) component] is preferably 0.001 or more or 0.005 or more, more preferably 0.01 or more, 0.02 or more or 0.05 or more, further preferably 0.08 or more, 0.1 or more or 0.2 or more, and particularly preferably 0.4 or more, 0.5 or more or 0.6 or more. The upper limit is preferably 50 or less or 30 or less, more preferably 20 or less, 10 or less or 8 or less, further preferably 5 or less, 3 or less or 2 or less, and particularly preferably 1 or less, 0.9 or less or 0.8 or less.

[0337] When the resin composition of the first embodiment contains both component (F) and component (H), from the viewpoint of significantly obtaining the effects of the present invention, the mass ratio of component (F) to component (H) [(F) component / (H) component] is preferably 0.0001 or more, 0.0005 or more, or 0.001 or more, more preferably 0.002 or more, 0.005 or more, or 0.008 or more, further preferably 0.01 or more, 0.02 or more, or 0.03 or more, and particularly preferably 0.05 or more, 0.06 or more, or 0.08 or more. The upper limit is preferably 10 or less or 8 or less, more preferably 5 or less or 2 or less, further preferably 1 or less, 0.8 or less, or 0.5 or less, and particularly preferably 0.2 or less, 0.1 or less, or 0.09 or less.

[0338] <(I) Organic Solvents>

[0339] The resin composition of the first embodiment of the present invention may optionally contain (I) an organic solvent, preferably (I) an organic solvent. By containing (I) an organic solvent in the resin composition, a resin composition varnish with a suitable viscosity can be obtained. One (I) organic solvent may be used alone, or two or more may be used in combination.

[0340] As an organic solvent (I), examples include organic solvents composed of atoms selected from carbon atoms, oxygen atoms, nitrogen atoms, phosphorus atoms, sulfur atoms, halogen atoms, and hydrogen atoms. From a safety point of view, the organic solvent (I) is preferably an organic solvent composed of atoms selected from carbon atoms, oxygen atoms, and hydrogen atoms, and more preferably an organic solvent composed of carbon atoms, oxygen atoms, and hydrogen atoms.

[0341] Examples of organic solvents (I) include glycol-based organic solvents, glycol ether-based organic solvents, glycol ether ester-based organic solvents, ketone-based organic solvents, ester-based organic solvents, ether-based organic solvents, alcohol-based organic solvents, aliphatic hydrocarbon-based organic solvents, aromatic organic solvents, nitrogen-based organic solvents, sulfur-based organic solvents, and halogen-based organic solvents. Examples of nitrogen-based organic solvents include amide-based organic solvents, urea-based organic solvents, and nitrile-based organic solvents. From a safety perspective, ester-based organic solvents, ketone-based organic solvents, glycol-based organic solvents, glycol ether-based organic solvents, glycol ether ester-based organic solvents, alcohol-based organic solvents, or aromatic organic solvents are preferred as (I) organic solvents; ester-based organic solvents, glycol ether-based organic solvents, ketone-based organic solvents, alcohol-based organic solvents, or aromatic organic solvents are more preferred; glycol ether-based organic solvents, ketone-based organic solvents, alcohol-based organic solvents, or aromatic organic solvents are even more preferred; and ketone-based organic solvents are particularly preferred.

[0342] Examples of diol-based organic solvents include ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, and 1,3-propanediol.

[0343] Examples of glycol ether-based organic solvents include, for instance, ethylene glycol monomethyl ether (also known as methyl cellosolve), ethylene glycol monoethyl ether (also known as cellosolve), ethylene glycol monopropyl ether (also known as propyl cellosolve), ethylene glycol monobutyl ether (also known as butyl cellosolve), ethylene glycol monoisobutyl ether (also known as isobutyl cellosolve), ethylene glycol monotert-butyl ether (also known as tert-butyl cellosolve), and ethylene glycol monohexyl ether; diethylene glycol monomethyl ether (also known as methyl carbitol), diethylene glycol monoethyl ether (also known as... Carbitols include carbitol, diethylene glycol monopropyl ether (also known as propyl carbitol), diethylene glycol monobutyl ether (DB) (also known as butyl carbitol), etc.; propylene glycol monomethyl ether (PGM, also known as 1-methoxy-2-propanol), propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, etc.; dipropylene glycol ethers such as dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol monopropyl ether, dipropylene glycol monobutyl ether, etc., preferably propylene glycol ethers, more preferably propylene glycol monomethyl ether.

[0344] Examples of glycol ether ester-based organic solvents include, for example, ethylene glycol monomethyl ether acetate (also known as methyl cellosolve acetate), ethylene glycol monoethyl ether acetate (also known as cellosolve acetate), ethylene glycol monobutyl ether acetate (also known as butyl cellosolve acetate), etc.; carbitol esters such as diethylene glycol monoethyl ether acetate (EDGAc) (also known as carbitol acetate) and diethylene glycol monobutyl ether acetate (also known as butyl carbitol acetate); propylene glycol ether esters such as propylene glycol monomethyl ether acetate (PGMEAc) and propylene glycol monoethyl ether acetate; and dipropylene glycol ether esters such as dipropylene glycol monomethyl ether acetate, etc., with carbitol esters being preferred, and diethylene glycol monoethyl ether acetate being more preferred.

[0345] Examples of ketone-based organic solvents include, for example, aliphatic acyclic ketones such as acetone, methyl ethyl ketone (MEK), diethyl ketone, 2-pentanone, methyl isobutyl ketone, 2-hexanone, 2-heptanone (MAK), and diisobutyl ketone; aliphatic cyclic ketones such as cyclopentanone, cyclohexanone (Anone), and 2-methylcyclohexanone; and aromatic ketones such as acetophenone, with methyl ethyl ketone (MEK) or cyclohexanone being preferred. The lower limit of the number of carbon atoms in the ketone-based organic solvent is preferably 2 or more, more preferably 3 or more, and even more preferably 4 or more. The upper limit of the number of carbon atoms in the ketone-based organic solvent is preferably 10 or less, more preferably 8 or less, and even more preferably 6 or less.

[0346] Ester-based organic solvents are organic solvents with ester structures that are not comparable to those of glycol ether ester-based organic solvents. Examples include fatty acid alkyl esters such as methyl acetate, ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, isobutyl acetate, sec-butyl acetate, tert-butyl acetate, n-pentyl acetate, isopentyl acetate, ethyl propionate, propyl propionate, and isopropyl propionate; hydroxy acid alkyl esters such as methyl lactate, ethyl lactate, and butyl lactate; keto acid alkyl esters such as methyl acetoacetate and ethyl acetoacetate; lactones such as γ-butyrolactone and α-acetyl-γ-butyrolactone; and aromatic esters such as methyl benzoate and ethyl benzoate. Lactones are preferred as ester-based organic solvents. Furthermore, the number of carbon atoms in ester-based organic solvents is preferably 3 to 9.

[0347] Ether-based organic solvents are organic solvents with ether structures that are not equivalent to those of glycol ether-based and glycol ether ester-based organic solvents. Examples include aliphatic acyclic ethers such as dimethyl ether, diethyl ether, methyl ethyl ether, diisopropyl ether, dibutyl ether, methyl tert-butyl ether, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, and triethylene glycol dimethyl ether; aliphatic cyclic ethers such as tetrahydrofuran, 1,4-dioxane, and 1,3-dioxolane; and aromatic ethers such as anisole and phenethyl ether. The preferred number of carbon atoms in ether-based organic solvents is 2 to 9.

[0348] Alcohol-based organic solvents are organic solvents with alcohol structures that are not comparable to those of glycol-based and glycol ether-based organic solvents. Examples include aliphatic noncyclic alcohols such as methanol, ethanol, n-propanol, 2-propanol (also known as isopropanol), n-butanol, isobutanol, sec-butanol, tert-butanol, n-pentanol, isopentanol, sec-pentanol, tert-pentanol, neopentanol, n-hexanol, n-heptanol, isoheptanol, n-octanol, and 2-ethylhexanol; aliphatic cyclic alcohols such as cyclohexanol; and aromatic alcohols such as benzyl alcohol and phenethyl alcohol. Aliphatic noncyclic alcohols are preferred, and 2-propanol is more preferred.

[0349] Examples of aliphatic hydrocarbon organic solvents include n-pentane, n-hexane, 2-methylpentane (also known as isohexane), n-heptane, n-octane, cyclopentane, cyclohexane, methylcyclohexane, ethylcyclohexane, and decahydronaphthalene. The number of carbon atoms in aliphatic hydrocarbon organic solvents is preferably 5 to 10.

[0350] Examples of aromatic organic solvents include benzene, toluene, o-xylene, m-xylene, p-xylene, and ethylbenzene. 6-8 Aromatic hydrocarbons; 1,2,3-trimethylbenzene, 1,3,5-trimethylbenzene (also known as mesitylene), 1,2,4-trimethylbenzene, 4-ethyltoluene, 3-ethyltoluene, 2-ethyltoluene, etc. C9 aromatic hydrocarbons; 1,2-diethylbenzene, 1,3-diethylbenzene, 1,4-diethylbenzene, 3-ethyl-o-xylene, 4-ethyl-o-xylene, 2-ethyl-p-xylene, 1,2,3,5-tetramethylbenzene, tetrahydronaphthalene, etc. 10 Aromatic hydrocarbons; aromatic heterocyclic compounds such as pyridine, furan, and thiophene, with toluene being preferred. The number of carbon atoms in the aromatic organic solvent is preferably 6 to 10.

[0351] Examples of amide-based organic solvents include, for example, aliphatic acyclic amides such as N,N-dimethylacetamide and N,N-dimethylformamide; lactams such as N-methyl-2-pyrrolidone and N-cyclohexyl-2-pyrrolidone; and phosphoroamides such as hexamethylphosphoramide. The preferred number of carbon atoms in amide-based organic solvents is 2 to 10.

[0352] Examples of urea-based organic solvents include tetramethylurea and 1,3-dimethyl-2-imidazolinone.

[0353] Examples of nitrile organic solvents include acetonitrile, propionitrile, and benzonitrile. The preferred number of carbon atoms in nitrile organic solvents is 2 to 10.

[0354] Examples of sulfur-based organic solvents include, for example, dimethyl sulfoxide.

[0355] Examples of halogenated organic solvents include chloroform, dichloromethane, carbon tetrachloride, and 1,2-dichloroethane. The preferred number of carbon atoms in halogenated organic solvents is 1 to 10.

[0356] Among these, as (I) organic solvents, γ-butyrolactone, methyl ethyl ketone (MEK), cyclopentanone, cyclohexanone, propylene glycol, diethylene glycol monoethyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, 2-propanol or toluene are preferred, methyl ethyl ketone (MEK), cyclohexanone, diethylene glycol monoethyl ether acetate, γ-butyrolactone, propylene glycol monomethyl ether, 2-propanol or toluene are even more preferred, methyl ethyl ketone (MEK), cyclohexanone, propylene glycol monomethyl ether, 2-propanol or toluene are even more preferred, and methyl ethyl ketone (MEK) or cyclohexanone are particularly preferred.

[0357] When the resin composition of the first embodiment of the present invention contains (I) organic solvent, in terms of the content of component (I), when all components in the resin composition are set to 100% by mass, it is preferably 1% by mass or more or 3% by mass or more, more preferably 5% by mass or more or 8% by mass or more, further preferably 10% by mass or more or 12% by mass or more, particularly preferably 15% by mass or more or 18% by mass or more. The upper limit is preferably 50% by mass or less, more preferably 45% by mass or less or 40% by mass or less, further preferably 35% by mass or less or 30% by mass or less, particularly preferably 25% by mass or less or 22% by mass or less.

[0358] <(J) Other Additives>

[0359] Regarding the resin composition of the first embodiment of the present invention, other additives may be included as optional components without hindering the purpose of the present invention. Examples of such additives include, for instance, peroxide-based free radical polymerization initiators, azo-based free radical polymerization initiators, and other free radical polymerization initiators; organometallic compounds such as organocopper compounds, organozinc compounds, and organocobalt 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 organosilicon-based and acrylic polymer-based leveling agents; thickeners such as bentonite and montmorillonite; defoamers such as organosilicon-based, acrylic-based, fluorine-based, and vinyl resin-based defoamers; ultraviolet absorbers such as benzotriazole-based ultraviolet absorbers; adhesion enhancers such as ureasilanes; and triazole-based and tetraazole-based adhesion enhancers. This includes binding agents such as binding agents and triazine-based binding agents; antioxidants such as hindered phenolic antioxidants; fluorescent whitening agents such as stilbene derivatives; surfactants such as fluorine-based and organosilicon-based surfactants; flame retardants such as phosphorus-based (e.g., phosphate ester compounds, phosphazene compounds, phosphonic acid compounds, red phosphorus), nitrogen-based (e.g., melamine sulfate), halogen-based, and inorganic (e.g., antimony trioxide); dispersants such as phosphate ester-based, polyoxyethylene-based, acetylene-based, organosilicon-based, anionic, and cationic dispersants; and stabilizers such as borate ester-based, titanate ester-based, aluminate ester-based, zirconate ester-based, isocyanate-based, carboxylic acid-based, and carboxylic anhydride-based stabilizers. The content of this additive can be determined according to the required properties of the resin composition. Furthermore, the components (A) to (I) above may function as free radical polymerization initiators, organometallic compounds, colorants, polymerization inhibitors, thickeners, defoamers, ultraviolet absorbers, adhesion enhancers, adhesion promoters, antioxidants, fluorescent whitening agents, flame retardants, dispersants, stabilizers, etc. In this case, the component is not component (J), but is considered as a component of components (A) to (I).

[0360] [Resin Composition of the Second Embodiment]

[0361] The resin composition of the second embodiment of the present invention contains (A) a cyclic ether compound with a four-membered ring or less, (B) a curing agent, (C) an inorganic filler, (2D-1) aluminum, and (2D-2) an organic ligand having an oxygen atom as a coordinating atom. Component (A) contains (A1) a cyclic ether compound with a four-membered ring or less that has cationic polymerization properties. By including components (A) to (2D-2) in the resin composition, a cured product exhibiting excellent dielectric loss tangent can be obtained even at high temperatures (100°C). That is, a resin composition that contributes to a low dielectric loss tangent in the cured product can be produced, particularly a resin composition that contributes to a cured product exhibiting an even lower dielectric loss tangent even at high temperatures (100°C). The reason for this is not clear, but it is speculated as follows. It is believed that (2D-1) aluminum and (2D-2) an organic ligand having an oxygen atom as a coordinating atom form an aluminum complex in the resin composition. Furthermore, it is speculated that during the thermosetting of the resin composition, the cyclic ether compound (A1) with a four-membered ring or smaller that has cationic polymerization properties reacts with the hydroxyl groups on the surface of the inorganic filler (C) using the aluminum complex as a Lewis acid catalyst, forming a cross-linked structure between the inorganic filler and the resin portion. This suppresses the molecular motion of polymer molecules in the cured product, thus exhibiting excellent dielectric loss tangent even at high temperatures (100°C). The inventors have also confirmed that the resin composition of the second embodiment of the present invention also exhibits excellent dielectric loss tangent at room temperature (23°C), resulting in a cured product with a low coefficient of linear expansion and a high glass transition temperature. The resin composition of the second embodiment, as component (A), may contain a cyclic ether compound (hereinafter referred to as "component (A2)") other than component (A1). In addition, the resin composition of the second embodiment may further contain optional components in combination with components (A) to (2D-2). Optional components may include, for example, (E) a free radical curable resin, (F) a curing accelerator, (G) an organic filler, (H) a thermoplastic resin, (I) an organic solvent, and (J) other additives. Hereinafter, the components contained in the resin composition of the second embodiment will be described.

[0362] <(A) Cyclic ether compounds with four or fewer members>

[0363] The resin composition of the second embodiment of the present invention contains a cyclic ether compound with a four-membered ring or less (A). The cyclic ether compound with a four-membered ring or less (A) in the second embodiment is the same as the cyclic ether compound with a four-membered ring or less (A) in the first embodiment.

[0364] <(A1) Cyclic ether compounds with four or fewer members that exhibit cationic polymerization>

[0365] In the resin composition of the second embodiment of the present invention, component (A) comprises a cyclic ether compound (A1) having a four-membered ring or less with cationic polymerization properties. The cyclic ether compound (A1) having a four-membered ring or less with cationic polymerization properties according to the second embodiment is the same as the cyclic ether compound (A1) having a four-membered ring or less with cationic polymerization properties according to the first embodiment.

[0366] <Cyclic ether compounds with a ring smaller than four members other than (A1)>

[0367] In the resin composition of the second embodiment of the present invention, component (A) may include a cyclic ether compound with a four-membered ring or less other than component ((A2)), preferably including component (A2). The component (A2) in the second embodiment is the same as the component (A2) in the first embodiment.

[0368] <(B) Curing Agent>

[0369] The resin composition of the second embodiment of the present invention contains (B) a curing agent. The (B) curing agent involved in the second embodiment is the same as the (B) curing agent involved in the first embodiment.

[0370] <(C) Inorganic filler materials>

[0371] The resin composition of the second embodiment of the present invention contains (C) inorganic filler. The (C) inorganic filler in the second embodiment is the same as the (C) inorganic filler in the first embodiment.

[0372] <(2D-1)Aluminum>

[0373] The resin composition of the second embodiment of the present invention contains (2D-1) aluminum. In the present invention, when simply referred to as "aluminum," it includes elements, compounds, and ions having aluminum atoms. However, when equivalent to the (C) inorganic filler material, it is excluded from the (2D-1) component. The (2D-1) component is preferably aluminum ions, more preferably trivalent aluminum ions, and even more preferably aluminum complexes. In another embodiment, the (2D-1) component may be ionic aluminum, trivalent aluminum, mononuclear aluminum, etc. That is, the (2D-1) component preferably contains aluminum ions, more preferably trivalent aluminum ions, and even more preferably aluminum complexes. In another embodiment, the (2D-1) component may contain ionic aluminum, trivalent aluminum, mononuclear aluminum, etc. When the (2D-1) component contains aluminum complexes, the preferred embodiment of the aluminum complex involved in the (2D-1) component is the same as the preferred embodiment of the aluminum complex involved in the (1D) component.

[0374] Other specific examples of (2D-1) components include aluminum glycinate, aluminum potassium sulfate, aluminum ammonium sulfate, aluminum formate, aluminum sulfate, and aluminum phosphate.

[0375] Regarding the content of component (2D-1), from the viewpoint of significantly obtaining the effects of the present invention, based on the non-volatile components in the resin composition, it is preferably 0.1 ppm or more by mass or 0.5 ppm or more by mass, more preferably 1 ppm or more by mass or 2 ppm or more by mass, further preferably 5 ppm or more by mass or 8 ppm or more by mass, and particularly preferably 10 ppm or more by mass, 11 ppm or more by mass, or 12 ppm or more by mass. In one embodiment, it may be 15 ppm or more by mass, 18 ppm or more by mass, 20 ppm or more by mass, 22 ppm or more by mass, 24 ppm or more by mass, etc. The upper limit is preferably 2000 ppm or less by mass, 1500 ppm or less by mass, or 1000 ppm or less by mass, more preferably 800 ppm or less by mass, 500 ppm or less by mass, or 200 ppm or less by mass, further preferably 100 ppm or less by mass, 80 ppm or less by mass, or 60 ppm or less by mass, and particularly preferably 50 ppm or less by mass, 40 ppm or less by mass, 35 ppm or less by mass, or 30 ppm or less by mass. When (2D-1) is an aluminum complex, the above content refers to the content of aluminum ions, excluding the content of ligands. Similarly, when (2D-1) is a compound containing aluminum, the above content refers to the content of aluminum, excluding the content of other elements from that compound.

[0376] Regarding the content of component (2D-1), based on the resin component in the resin composition, from the viewpoint of significantly obtaining the effects of the present invention, it is preferably 0.2 ppm or more by mass or 0.5 ppm or more by mass, more preferably 1 ppm or more by mass, 2 ppm or more by mass or 5 ppm or more by mass, further preferably 8 ppm or more by mass, 10 ppm or more by mass or 15 ppm or more by mass, and particularly preferably 20 ppm or more by mass, 25 ppm or more by mass or 30 ppm or more by mass. In one embodiment, it may be 40 ppm or more by mass, 45 ppm or more by mass, 50 ppm or more by mass, 55 ppm or more by mass, 60 ppm or more by mass, etc. The upper limit is preferably 5000 ppm or less by mass, 3000 ppm or less by mass, or 2000 ppm or less by mass, more preferably 1000 ppm or less by mass, 800 ppm or less by mass, or 600 ppm or less by mass, further preferably 500 ppm or less by mass, 400 ppm or less by mass, or 350 ppm or less by mass, and particularly preferably 300 ppm or less by mass, 250 ppm or less by mass, 200 ppm or less by mass, or 180 ppm or less by mass. In another embodiment, the content may be 160 ppm or less by mass, 140 ppm or less by mass, 120 ppm or less by mass, 100 ppm or less by mass, 90 ppm or less by mass, 80 ppm or less by mass, 70 ppm or less by mass, etc. When the (2D-1) component is an aluminum complex, the above content refers to the content of aluminum ions and does not include the content of ligands. Similarly, when the (2D-1) component is a compound containing aluminum, the above content refers to the content of aluminum and does not include the content of other elements from the compound.

[0377] <(2D-2) Organic ligands with oxygen atoms as coordinating atoms>

[0378] The resin composition of the second embodiment of the present invention contains (2D-2) organic ligands having oxygen atoms as coordinating atoms. The (2D-2) component may be used alone or in combination of two or more.

[0379] Examples of organic ligands with oxygen atoms as coordinating atoms in (2D-2) include alcohols, alkoxides, phenols, phenol salts, β-diketones, β-diketenolides, β-keto esters, β-keto ester enolides, carboxylic acids, and carboxylic acid ions. In one embodiment, the (2D-2) component preferably includes one or more organic ligands selected from alcohols, alkoxides, β-diketones, β-diketenolides, β-keto esters, and β-keto ester enolides, and more preferably includes one or more organic ligands selected from β-diketones, β-diketenolides, β-keto esters, and β-keto ester enolides.

[0380] The alcohol involved in component (2D-2) is the same alcohol that is the ligand of component (1D).

[0381] The alkoxide involved in component (2D-2) is the same as the alkoxide that is the ligand of component (1D).

[0382] The β-diketone involved in component (2D-2) is the same as the β-diketone that is the ligand of component (1D).

[0383] The β-diketenyl alcohol involved in component (2D-2) is the same as the β-diketenyl alcohol that is the ligand of component (1D).

[0384] The β-keto esters involved in the (2D-2) component are the same as those that are ligands of the (1D) component.

[0385] The β-keto ester enolide involved in component (2D-2) is the same as the β-keto ester enolide that is the ligand of component (1D).

[0386] The carboxylic acid involved in component (2D-2) is the same carboxylic acid that is the ligand of component (1D).

[0387] The carboxylic acid ion involved in the (2D-2) component is the same as the carboxylic acid ion of the ligand that is the (1D) component.

[0388] Regarding the (2D-2) component, it can form a complex with the aforementioned (2D-1) aluminum in the resin composition. Alternatively, in another embodiment, the (2D-2) component is preferably included in the resin composition as a different component from the aforementioned (2D-1).

[0389] Commercially available reagents can be used as the (2D-2) component. Alternatively, the resin composition can contain aluminum complexes as specific examples of the (1D) component described above, or ligands that dissociate in the resin composition can be used as the (2D-2) component.

[0390] Regarding the content of component (2D-2), from the viewpoint of significantly obtaining the effects of the present invention, when the non-volatile component in the resin composition is set to 100% by mass, it is preferably 0.0001% by mass or more or 0.0005% by mass or more, more preferably 0.001% by mass or more or 0.002% by mass or more, further preferably 0.005% by mass or more or 0.008% by mass or more, and particularly preferably 0.01% by mass or more, 0.015% by mass or more, or 0.016% by mass or more. In addition, in one embodiment, it may be 0.02% by mass or more, 0.025% by mass or more, 0.03% by mass or more, 0.032% by mass or more, etc. The upper limit is preferably 2.00% by mass or less or 1.00% by mass, more preferably 0.80% by mass or less or 0.50% by mass, further preferably 0.20% by mass or less, 0.10% by mass or less or 0.08% by mass, and particularly preferably 0.07% by mass or less, 0.06% by mass or less, 0.05% by mass or less, 0.045% by mass or less, 0.04% by mass or less or 0.035% by mass.

[0391] Regarding the content of component (2D-2), from the viewpoint of significantly obtaining the effects of the present invention, when the resin component in the resin composition is set to 100% by mass, it is preferably 0.001% by mass or more or 0.002% by mass or more, more preferably 0.005% by mass or more or 0.008% by mass or more, further preferably 0.01% by mass or more or 0.02% by mass or more, particularly preferably 0.05% by mass or more, 0.06% by mass or more, or 0.08% by mass or more. The upper limit is preferably 10% by mass or less or 8% by mass or less, more preferably 5% by mass or less or 2% by mass or less, further preferably 1% by mass or less, 0.8% by mass or less or 0.5% by mass or less, particularly preferably 0.2% by mass or less, 0.18% by mass or less, 0.15% by mass or less, 0.13% by mass or less, or 0.1% by mass or less.

[0392] Regarding the total content of components (2D-1) and (2D-2), when the non-volatile component in the resin composition is set to 100% by mass, from the viewpoint of significantly obtaining the effects of the present invention, it is preferably 0.0001% by mass or more or 0.0005% by mass or more, more preferably 0.001% by mass or more or 0.002% by mass or more, further preferably 0.005% by mass or more or 0.008% by mass or more, and particularly preferably 0.01% by mass or more, 0.015% by mass or more, or 0.017% by mass or more. Additionally, in one embodiment, it may be 0.02% by mass or more, 0.025% by mass or more, 0.03% by mass or more, 0.035% by mass or more, etc. The upper limit is preferably 2.00% by mass or less or 1.00% by mass or less, more preferably 0.80% by mass or less or 0.50% by mass or less, further preferably 0.20% by mass or less, 0.15% by mass or less, 0.10% by mass or less or 0.08% by mass or less, particularly preferably 0.07% by mass or less, 0.06% by mass or less, 0.05% by mass or less or 0.04% by mass or less. In one embodiment, when the total content of the (2D-1) component and the (2D-2) component is set to 100% by mass, the non-volatile component in the resin composition is preferably 0.01 to 0.20% by mass, more preferably 0.01 to 0.15% by mass.

[0393] Regarding the total content of components (2D-1) and (2D-2), when the resin content in the resin composition is set to 100% by mass, from the viewpoint of significantly obtaining the effects of the present invention, it is preferably 0.001% by mass or more or 0.002% by mass or more, more preferably 0.005% by mass or more or 0.008% by mass or more, further preferably 0.01% by mass or more or 0.02% by mass or more, particularly preferably 0.05% by mass or more, 0.06% by mass or more, or 0.08% by mass or more. The upper limit is preferably 10% by mass or less or 8% by mass or less, more preferably 5% by mass or less or 2% by mass or less, further preferably 1% by mass or less, 0.8% by mass or less or 0.5% by mass or less, particularly preferably 0.2% by mass or less, 0.18% by mass or less, 0.15% by mass or less, 0.12% by mass or less, or 0.1% by mass or less.

[0394] <(E) Free Radical Curing Resins>

[0395] The resin composition of the second embodiment of the present invention may optionally contain an (E) radical-curable resin. The (E) radical-curable resin involved in the second embodiment is the same as the (E) radical-curable resin involved in the first embodiment.

[0396] <(F) Curing Accelerator>

[0397] The resin composition of the second embodiment of the present invention may optionally contain a (F) curing accelerator, preferably a (F) curing accelerator. The (F) curing accelerator involved in the second embodiment is the same as the (F) curing accelerator involved in the first embodiment.

[0398] <(G) Organic filler materials>

[0399] The resin composition of the second embodiment of the present invention may optionally contain an organic filler (G). Preferably, the resin composition of the second embodiment contains at least one of the organic filler (G) and the thermoplastic resin described later (H). The organic filler (G) involved in the second embodiment is the same as the organic filler (G) involved in the first embodiment.

[0400] <(H) Thermoplastic Resin>

[0401] The resin composition of the second embodiment of the present invention may optionally contain a (H) thermoplastic resin. The resin composition of the second embodiment preferably contains at least one of the (G) organic filler and the (H) thermoplastic resin described above. The (H) thermoplastic resin involved in the second embodiment is the same as the (H) thermoplastic resin involved in the first embodiment.

[0402] <(I) Organic Solvents>

[0403] The resin composition of the second embodiment of the present invention may optionally contain (I) an organic solvent, preferably (I) an organic solvent. The (I) organic solvent involved in the second embodiment is the same as the (I) organic solvent involved in the first embodiment.

[0404] <(J) Other Additives>

[0405] Regarding the resin composition of the second embodiment of the present invention, it may further contain (J) other additives as optional components, without hindering the purpose of the present invention. The (J) other additives involved in the second embodiment are the same as those involved in the first embodiment.

[0406] <Content of each component in the resin composition of the second embodiment>

[0407] In the resin composition of the second embodiment, considering the total content of components (A), (B), (C), (2D-1), and (2D-2), when the non-volatile components in the resin composition are set to 100% by mass, from the viewpoint of significantly obtaining the effects of the present invention, it is preferably 30% by mass or more or 40% by mass or more, more preferably 50% by mass or more or 60% by mass or more, further preferably 70% by mass or more, 80% by mass or more or 85% by mass or more, and particularly preferably 90% by mass or more, 95% by mass or more or 97% by mass or more. In another embodiment, it may be 98% by mass or more, 98.5% by mass or more, etc. The upper limit may be 100% by mass, and it may be 99.9% by mass or less, 99.8% by mass or less, 99.5% by mass or less, 99.2% by mass or less, etc.

[0408] Regarding the mass ratio of (2D-1) component to (Al) component [(2D-1) component / (Al) component], from the viewpoints of significantly obtaining the effects of the present invention, reducing the coefficient of linear expansion of the cured product, and increasing the glass transition temperature of the cured product, a mass ratio of 1×10⁻⁶ is preferred. -5 Above or 2×10 -5 The above is preferred, with 5×10 being more ideal. -5 Above or 8×10 -5 The above is further preferred to be 1×10 -4 Above or 2×10 -4 The above is particularly preferred, with 5×10 -4 Above or 7×10 -4 That's all. Additionally, in one embodiment, it can be 8 × 10. -4 Above, 1×10 -3 Above, 2×10 -3 Above, 2.5×10 -3 The above, etc. The upper limit is preferably below 1 or 8 × 10. -1 The following is more preferably 5×10 -1 Below or 2×10 -1 Hereinafter, 1×10 is further preferred. -1 Below or 8×10 -2 The following is particularly preferred: 5×10 -2 Below or 2×10 -2 The following. Additionally, in one embodiment, it can be 1×10. -2 Below, 8×10 -3 Below, 5×10 -3 Below, 4×10 -3 Below, 3×10 -3 The following, etc.

[0409] In the case where the resin composition of the second embodiment contains component (A2), from the viewpoint of significantly obtaining the effects of the present invention, the mass ratio of component (2D-1) to component (A2) [(2D-1) component / (A2) component] is preferably 1×10⁻⁶. -6 Above or 2×10 -6 The above is preferred, with 5×10 being more ideal. -6 Above or 8×10 -6 The above is further preferred to be 1×10 -5 Above or 2×10 -5 The above is particularly preferred, with 5×10 -5 Above, 8×10 -5 Above or 9×10 -5 That's all. The upper limit is preferably 1×10. -1 Below, 8×10 -2 Below or 5×10 -2 The following is more preferably 2×10 -2 Below, 1×10 -2 Below or 8×10 -3 The following is a further preferred option: 5×10 -3 Below, 2×10 -3 Below or 1×10 -3 The following is particularly preferred: 8×10 -4 Below, 5×10 -4 Below or 3×10 -4 The following. Additionally, in one embodiment, it can be 3 × 10. -4 Below, 2×10 -4 Below, 1.5×10 -4 Below, 1×10 -4 The following, etc.

[0410] Regarding the mass ratio of component (2D-1) to component (A) [(2D-1) component / (A) component], from the viewpoint of significantly obtaining the effects of the present invention, 1×10⁻⁶ is preferred. -6 Above or 2×10 -6 The above is preferred, with 5×10 being more ideal. -6 Above or 8×10 -6 The above is further preferred to be 1×10 -5 Above or 2×10 -5 The above is particularly preferred, with 5×10 -5 Above, 8×10 -5 Above or 9×10 -5 That's all. The upper limit is preferably 1×10. -1 Below, 8×10 -2 Below or 5×10 -2 The following is more preferably 2×10-2 Below, 1×10 -2 Below or 8×10 -3 The following is a further preferred option: 5×10 -3 Below, 2×10 -3 Below or 1×10 -3 The following is particularly preferred: 8×10 -4 Below, 5×10 -4 Below or 3×10 -4 The following. Additionally, in one embodiment, it can be 3 × 10. -4 Below, 2×10 -4 Below, 1.5×10 -4 Below, 1×10 -4 The following, etc.

[0411] From the viewpoint of significantly obtaining the effects of the present invention, the mass ratio of component (2D-1) to component (B) [(2D-1) component / (B) component] is preferably 1×10⁻⁶. -6 Above, 2×10 -6 Above or 5×10 -6 The above is preferred, specifically 8×10 -6 Above, 1×10 -5 Above or 2×10 -5 The above is further optimized to be 5×10 -5 Above, 8×10 -5 Above or 1×10 -4 The above is particularly preferred, with 1.5 × 10⁻⁶ being the optimal value. -4 Above, 1.8×10 -4 Above or 2×10 -4 That's all. The upper limit is preferably 1×10. -1 Below or 8×10 -2 The following is more preferably 5×10 -2 Below, 2×10 -2 Below or 1×10 -2 The following is a further preferred option: 8×10 -3 Below, 5×10 -3 Below or 2×10 -3 The following is particularly preferred: 1×10 -3 Below, 8×10 -4 Below or 6×10 -4 The following. Additionally, in one embodiment, it can be 6 × 10. -4 Below, 5×10 -4 Below, 4×10 -4 Below, 3×10 -4 The following, etc.

[0412] Regarding the mass ratio of component (2D-1) to component (C) [(2D-1) component / (C) component], from the viewpoint of significantly obtaining the effects of the present invention, 1×10⁻⁶ is preferred. -7 Above, 2×10 -7 Above or 5×10 -7 The above is preferred, specifically 8×10 -7 Above, 1×10 -6 Above or 2×10 -6 The above is further optimized to be 5×10 -6 Above, 8×10 -6 Above or 1×10 -5 The above is particularly preferred, with 1.5 × 10⁻⁶ being the optimal value. -5 Above, 2×10 -5 Above or 2.5×10 -5 That's all. Additionally, in one embodiment, it can be 3 × 10. -5 Above, 4×10 -5 The above is preferred. The upper limit is preferably 1×10. -2 Below or 8×10 -3 The following is more preferably 5×10 -3 Below, 2×10 -3 Below or 1×10 -3 The following is a further preferred option: 8×10 -4 Below, 5×10 -4 Below or 2×10 -4 The following is particularly preferred: 1×10 -4 Below, 8×10 -5 Below, 6×10 -5 Below or 5×10 -5 the following.

[0413] In the case where the resin composition of the second embodiment contains component (E), from the viewpoint of significantly obtaining the effects of the present invention, the mass ratio of component (2D-1) to component (E) [(2D-1) component / (E) component] is preferably 1×10⁻⁶. -5 Above or 2×10 -5 The above is preferred, with 5×10 being more ideal. -5 Above, 8×10 -5 Above or 1×10 -4 The above is further preferred to be 2×10 -4 Above, 5×10 -4 Above or 8×10 -4 The above is particularly preferred, with 1×10 -3 Above, 1.2×10 -3 or above 1.4×10 -3 The above. The upper limit is preferably below 1 or 5 × 10.-1 Hereinafter, 1×10 is more preferred. -1 Below or 8×10 -2 The following is a further preferred option: 5×10 -2 Below, 2×10 -2 Below or 1×10 -2 The following is particularly preferred: 8×10 -3 Below, 5×10 -3 Below, 3×10 -3 Below or 2×10 -3 the following.

[0414] In the case where the resin composition of the second embodiment contains component (F), from the viewpoint of significantly obtaining the effects of the present invention, the mass ratio of component (2D-1) to component (F) [(2D-1) component / (F) component] is preferably 0.0001 or more, more preferably 0.0005 or more or 0.0008 or more, further preferably 0.001 or more, 0.002 or more, or 0.005 or more, and particularly preferably 0.008 or more, 0.01 or more, or 0.015 or more. In another embodiment, it may be 0.02 or more, 0.022 or more, 0.025 or more, etc. The upper limit is preferably 5 or less or 2 or less, more preferably 1 or less or 0.8 or less, further preferably 0.5 or less, 0.2 or less or 0.1 or less, and particularly preferably 0.08 or less, 0.05 or less, 0.04 or less, or 0.03 or less.

[0415] In the case where the resin composition of the second embodiment contains component (G), from the viewpoint of significantly obtaining the effects of the present invention, the mass ratio of component (2D-1) to component (G) [(2D-1) component / (G) component] is preferably 5 × 10⁻⁶. -5 Above or 8×10 -5 The above is preferred to be 1×10 -4 Above, 2×10 -4 Above or 5×10 -4 The above is further optimized to 8×10 -4 Above, 1×10 -3 Above or 2×10 -3 The above is particularly preferred, with 3×10 -3 Above, 4×10 -3 Above or 5×10 -3 The above. The upper limit is preferably below 1 or 8 × 10. -1 The following is more preferably 5×10 -1 Below, 2×10 -1 Below or 1×10 -1 The following is a further preferred option: 8×10 -2Below, 5×10 -2 Below or 2×10 -2 The following is particularly preferred: 1×10 -2 Below, 8×10 -3 Below or 7×10 -3 the following.

[0416] In the case where the resin composition of the second embodiment contains the (H) component, from the viewpoint of significantly obtaining the effects of the present invention, the mass ratio of the (2D-1) component to the (H) component [(2D-1) component / (H) component] is preferably 1×10⁻⁶. -5 Above or 2×10 -5 The above is preferred, with 5×10 being more ideal. -5 Above, 8×10 -5 Above or 1×10 -4 The above is further preferred to be 2×10 -4 Above, 5×10 -4 Above or 8×10 -4 The above is particularly preferred, with 1×10 -3 Above, 1.5×10 -3 Above or 2×10 -3 The above. The upper limit is preferably below 1 or 5 × 10. -1 Hereinafter, 1×10 is more preferred. -1 Below, 8×10 -2 Below or 5×10 -2 The following is a further preferred option: 2×10 -2 Below, 1×10 -2 Below or 8×10 -3 The following is particularly preferred: 5×10 -3 Below, 4×10 -3 Below or 3×10 -3 the following.

[0417] Regarding the mass ratio of (2D-2) component to (A1) component [(2D-2) component / (A1) component], from the viewpoints of significantly obtaining the effects of the present invention, reducing the coefficient of linear expansion of the cured product, and increasing the glass transition temperature of the cured product, it is preferably 0.0001 or more or 0.0002 or more, more preferably 0.0005 or more or 0.0008 or more, further preferably 0.001 or more or 0.002 or more, and particularly preferably 0.005 or more, 0.006 or more, or 0.007 or more. In one embodiment, it may be 0.01 or more, 0.02 or more, 0.03 or more, etc. The upper limit is preferably 5 or less or 2 or less, more preferably 1 or less or 0.8 or less, further preferably 0.5 or less or 0.2 or less, and particularly preferably 0.1 or less, 0.08 or less, 0.06 or less, 0.05 or less, or 0.04 or less.

[0418] In the case where the resin composition of the second embodiment contains component (A2), from the viewpoint of significantly obtaining the effects of the present invention, the mass ratio of component (2D-2) to component (A2) [(2D-2) component / (A2) component] is preferably 1×10⁻⁶. -5 Above or 2×10 -5 The above is preferred, with 5×10 being more ideal. -5 Above or 8×10 -5 The above is further preferred to be 1×10 -4 Above, 2×10 -4 Above or 5×10 -4 The above is particularly preferred, with 8×10 -4 Above, 1×10 -3 or above 1.2×10 -3 The above. The upper limit is preferably below 1 or 5 × 10. -1 Hereinafter, 1×10 is more preferred. -1 Below or 8×10 -2 The following is a further preferred option: 5×10 -2 Below, 2×10 -2 Below or 1×10 -2 The following is particularly preferred: 8×10 -3 Below, 5×10 -3 Below, 2×10 -3 Below, 1.8×10 -3 Below or 1.5×10 -3 the following.

[0419] Regarding the mass ratio of component (2D-2) to component (A) [(2D-2) component / (A) component], from the viewpoint of significantly obtaining the effects of the present invention, 1×10⁻⁶ is preferred. -5 Above or 2×10-5 The above is preferred, with 5×10 being more ideal. -5 Above, 8×10 -5 Above or 1×10 -4 The above is further preferred to be 2×10 -4 Above, 5×10 -4 Above or 8×10 -4 The above is particularly preferred, with 1×10 -3 Above, 1.1×10 -3 or above 1.2×10 -3 The above. The upper limit is preferably below 1 or 5 × 10. -1 Hereinafter, 1×10 is more preferred. -1 Below, 8×10 -2 Below or 5×10 -2 The following is a further preferred option: 2×10 -2 Below, 1×10 -2 Below or 8×10 -3 The following is particularly preferred: 5×10 -3 Below, 3×10 -3 Below, 2×10 -3 Below, 1.8×10 -3 Below or 1.5×10 -3 the following.

[0420] Regarding the mass ratio of component (2D-2) to component (B) [(2D-2) component / (B) component], from the viewpoint of significantly obtaining the effects of the present invention, 1×10⁻⁶ is preferred. -5 Above or 5×10 -5 The above is preferred to be 1×10 -4 Above or 2×10 -4 The above is further optimized to be 5×10 -4 Above or 8×10 -4 The above is particularly preferred, with 1×10 -3 Above, 2×10 -3 Above or 2.5×10 -3 The above. The upper limit is preferably below 1 or 5 × 10. -1 Hereinafter, 1×10 is more preferred. -1 Below, 8×10 -2 Below or 5×10 -2 The following is a further preferred option: 2×10 -2 Below, 1×10 -2 Below or 8×10 -3 The following is particularly preferred: 6×10 -3 Below, 5×10 -3 Below, 4×10 -3 Below or 3×10-3 the following.

[0421] Regarding the mass ratio of (2D-2) component to (C) component [(2D-2) component / (C) component], from the viewpoint of significantly obtaining the effects of the present invention, 1×10⁻⁶ is preferred. -5 The above is preferred, specifically 2×10 -5 Above or 5×10 -5 The above is further optimized to 8×10 -5 Above or 1×10 -4 The above is particularly preferred, with 2×10 -4 Above or 3×10 -4 That's all. Additionally, in one embodiment, it can be 4 × 10. -4 Above, 5×10 -4 Above, 6×10 -4 The above is preferred. The upper limit is preferably 1×10. -1 Below or 8×10 -2 The following is more preferably 5×10 -2 Below or 2×10 -2 Hereinafter, 1×10 is further preferred. -2 Below, 8×10 -3 Below or 5×10 -3 The following is particularly preferred: 2×10 -3 Below, 1×10 -3 Below, 9×10 -4 Below, 8×10 -4 Below, 7×10 -4 Below or 6×10 -4 the following.

[0422] When the resin composition of the second embodiment contains component (E), from the viewpoint of significantly obtaining the effects of the present invention, the mass ratio of component (2D-2) to component (E) [(2D-2) component / (E) component] is preferably 0.0001 or more, 0.0002 or more, or 0.0005 or more, more preferably 0.0008 or more, 0.001 or more, or 0.002 or more, further preferably 0.005 or more, 0.008 or more, or 0.01 or more, and particularly preferably 0.015 or more, or 0.018 or more. The upper limit is preferably 2 or less, or 1 or less, more preferably 0.8 or less, 0.5 or less, or 0.2 or less, further preferably 0.1 or less, 0.08 or less, or 0.06 or less, and particularly preferably 0.05 or less, 0.04 or less, 0.03 or less, or 0.025 or less.

[0423] In the case where the resin composition of the second embodiment contains component (F), from the viewpoint of significantly obtaining the effects of the present invention, the mass ratio of component (2D-2) to component (F) [(2D-2) component / (F) component] is preferably 0.001 or more, more preferably 0.01 or more or 0.02 or more, further preferably 0.05 or more or 0.08 or more, and particularly preferably 0.1 or more or 0.15 or more. In another embodiment, it may be 0.2 or more, 0.3 or more, 0.32 or more, etc. The upper limit is preferably 50 or less or 20 or less, more preferably 10 or less or 8 or less, further preferably 5 or less, 2 or less or 1 or less, and particularly preferably 0.8 or less, 0.7 or less, 0.6 or less, 0.5 or less or 0.4 or less.

[0424] When the resin composition of the second embodiment contains component (G), from the viewpoint of significantly obtaining the effects of the present invention, the mass ratio of component (2D-2) to component (G) [(2D-2) component / (G) component] is preferably 0.0001 or more or 0.0005 or more, more preferably 0.001 or more or 0.002 or more, further preferably 0.005 or more, 0.008 or more or 0.01 or more, and particularly preferably 0.02 or more, 0.03 or more or 0.04 or more. The upper limit is preferably 5 or less or 2 or less, more preferably 1 or less or 0.8 or less, further preferably 0.5 or less, 0.2 or less or 0.1 or less, and particularly preferably 0.08 or less, 0.07 or less, 0.06 or less or 0.05 or less.

[0425] When the resin composition of the second embodiment contains the (H) component, from the viewpoint of significantly obtaining the effects of the present invention, the mass ratio of the (2D-2) component to the (H) component [(2D-2) component / (H) component] is preferably 0.0001 or more or 0.0005 or more, more preferably 0.001 or more or 0.002 or more, further preferably 0.005 or more, 0.008 or more or 0.01 or more, and particularly preferably 0.02 or more or 0.025 or more. The upper limit is preferably 5 or less or 2 or less, more preferably 1 or less or 0.8 or less, further preferably 0.5 or less, 0.2 or less or 0.1 or less, and particularly preferably 0.08 or less, 0.06 or less, 0.05 or less, 0.04 or less or 0.03 or less.

[0426] [Method for manufacturing the resin composition]

[0427] The resin composition of the present invention can be prepared by appropriately mixing the necessary components from components (A) to (J) above, and by mixing or blending using mixing means such as a three-roll mill, ball mill, bead mill, sand mill, or stirring means such as a super mixer, planetary mixer, or high-speed rotary mixer, as needed. As a component of the resin composition of the present invention, when using a product diluted with a solvent, a solid resin obtained by removing the solvent can be used, or the product diluted with a solvent can be used directly. The solvent portion can be used as (I) an organic solvent.

[0428] In one embodiment, the method for manufacturing the resin composition of the present invention comprises:

[0429] (i) The process of preparing a resin composition containing component (A2), (B) a curing agent, and (C) an inorganic filler, and

[0430] (ii) The process of mixing the resin composition of step (i), (A1) a cyclic ether compound with a four-membered ring or less that has cationic polymerization properties, i.e., component (D).

[0431] In step (i), a resin composition containing component (A2), curing agent, and inorganic filler is prepared. Hereinafter, the resin composition of step (i) will also be referred to as "resin composition (i)". Resin composition (i) may contain optional components such as (E) free radical curing resin, (F) curing accelerator, (G) organic filler, (H) thermoplastic resin, (I) organic solvent, and (J) other additives. For example, resin composition (i) can be prepared by mixing components (A2), (B), (C), and (D) to (J).

[0432] In step (ii), the resin composition (resin composition (i)) from step (i) is mixed with (A1) a cyclic ether compound with a four-membered ring or less that has cationic polymerization properties, and component (D). Hereinafter, the resin composition obtained in step (ii) will also be referred to as "resin composition (ii)". Resin composition (ii) is equivalent to the resin composition of the first embodiment of the present invention and the resin composition of the second embodiment of the present invention.

[0433] The resin composition (ii) manufactured as described above reduces the dielectric loss tangent of the cured product, particularly the dielectric loss tangent at high temperatures (100°C), compared to the reference resin composition (i). That is, according to the method for manufacturing the resin composition of the present invention, the dielectric loss tangent of the cured resin composition can be relatively reduced, particularly the dielectric loss tangent at high temperatures (100°C).

[0434] Methods to reduce the dielectric loss tangent

[0435] The method for reducing the dielectric loss tangent of the present invention includes the following steps: mixing other components constituting the resin composition, (A1) a cyclic ether compound having a four-membered ring or less with cationic polymerization properties, and (D) component.

[0436] Other components constituting the resin composition may include, for example, component (A2), (B) curing agent, (C) inorganic filler, (E) free radical curable resin, (F) curing accelerator, (G) organic filler, (H) thermoplastic resin, (I) organic solvent, and (J) other additives. There are no restrictions on the order or method of mixing the other components constituting the resin composition, (A1) cyclic ether compounds with a four-membered ring or less exhibiting cationic polymerization, and component (D). Regarding the resin composition after mixing components (A1) and (D), compared to the resin composition before mixing components (A1) and (D), the dielectric loss tangent of the cured product, particularly at high temperatures (100°C), is reduced. That is, according to the method for reducing the dielectric loss tangent of the present invention, the dielectric loss tangent of the cured resin composition can be relatively reduced, particularly at high temperatures (100°C).

[0437] In one embodiment, the method for reducing the dielectric loss tangent of the present invention preferably includes:

[0438] (I) The process of preparing the resin composition; and

[0439] (II) A process of mixing the resin composition of step (I), (A1) a cyclic ether compound with a four-membered ring or less that has cationic polymerization properties, and (D) component.

[0440] In step (I), a resin composition is prepared. Hereinafter, the resin composition of step (I) will also be referred to as "resin composition (I)". There are no particular limitations on the resin composition (I), but it is preferable to contain one or more components selected from (A2), (B) curing agent, and (C) inorganic filler, more preferably to contain two or more components selected from the above group, and even more preferably to contain (A2), (B) curing agent, and (C) inorganic filler. In addition, the resin composition step (I) may contain (E) free radical curable resin, (F) curing accelerator, (G) organic filler, (H) thermoplastic resin, (I) organic solvent, (J) other additives, etc. As for the resin composition (I), it can be prepared by, for example, mixing components (A2), (B), (C), and (D) to (J).

[0441] In step (II), the resin composition (resin composition (I)) from step (I) is mixed with (A1) a cyclic ether compound with a four-membered ring or less that has cationic polymerization properties, and component (D). Hereinafter, the resin composition obtained in step (II) will also be referred to as "resin composition (II)".

[0442] Regarding the aforementioned resin composition (II), compared to the reference resin composition (I), the dielectric loss tangent of the cured product, particularly the dielectric loss tangent at high temperature (100°C), is reduced. That is, according to the method for reducing the dielectric loss tangent of the present invention, the dielectric loss tangent of the cured resin composition can be relatively reduced, particularly the dielectric loss tangent at high temperature (100°C).

[0443] [Properties and uses of the resin composition]

[0444] In one embodiment, the cured resin composition of the present invention has the following characteristic: a low dielectric loss tangent (Df) at room temperature (23°C). For example, when measured at 5.8 GHz and 23°C as described in the section "(3) Measurement of Dielectric Loss Tangent (Dielectric Properties)" below, the dielectric loss tangent (Df) of the cured resin composition of the present invention is preferably 0.0100 or less or 0.0080 or less, more preferably 0.0060 or less or 0.0050 or less, even more preferably 0.0044 or less or 0.0040 or less, and particularly preferably 0.0035 or less or 0.0030 or less. There is no particular limitation on the lower limit, and it can be 0.0001 or more or 0.0010 or more, etc.

[0445] In one embodiment, the cured product of the resin composition of the present invention has the following characteristics:

[0446] Even at high temperatures (100°C), the dielectric loss tangent (Df) remains low. For example, as described in section "(3) Measurement of Dielectric Loss Tangent (Dielectric Properties)" below, when measured at 5.8 GHz and 100°C, the dielectric loss tangent (Df) of the cured resin composition of the present invention is preferably 0.0100 or less or 0.0080 or less, more preferably 0.0060 or less or 0.0055 or less, even more preferably 0.0050 or less, 0.0048 or less or 0.0046 or less, and particularly preferably 0.0044 or less, 0.0040 or less or 0.0035 or less. There is no particular limitation on the lower limit, and it can be 0.0001 or more or 0.0010 or more, etc.

[0447] In one embodiment, the cured product of the resin composition of the present invention has the following characteristics:

[0448] The difference between the dielectric loss tangent (Df) at high temperature (100°C) and at room temperature (23°C) is small. This means that the temperature dependence of the dielectric loss tangent (Df) is small. When measured at 5.8 GHz, 23°C and 100°C as described in the section "(3) Measurement of Dielectric Loss Tangent (Dielectric Properties)" below, the difference between the dielectric loss tangent (Df) at high temperature (100°C) and at room temperature (23°C) is preferably 0.0030 or less or 0.0025 or less, more preferably 0.0020 or less, 0.0015 or less or 0.0012 or less, even more preferably 0.0010 or less, 0.0009 or less or 0.0008 or less, and particularly preferably 0.0007 or less, 0.0006 or less or 0.0005 or less. There is no specific limitation on the lower limit; it can be above 0.00001 or above 0.0001, etc.

[0449] In one embodiment, the cured resin composition of the present invention has the following characteristic: a high glass transition temperature (Tg). For example, as described in the section "(4) Determination of linear thermal expansion coefficient (CTE) and glass transition temperature (Tg)" below, when the glass transition temperature (Tg) is measured using a thermomechanical analysis apparatus with a tensile loading method (tension weight method), the glass transition temperature (Tg) of the cured resin composition of the present invention is preferably 120°C or higher or 125°C or higher, more preferably 130°C or higher or 135°C or higher, further preferably 140°C or higher, 145°C or higher or 150°C or higher, and particularly preferably 152°C or higher, 154°C or higher or 156°C or higher. There is no particular limitation on the upper limit, and it can be 400°C or lower, 300°C or lower, etc.

[0450] In one embodiment, the cured resin composition of the present invention has the following characteristic: a low coefficient of linear thermal expansion (CTE). For example, when measured using a thermomechanical analysis apparatus and by a tensile loading method as described in section "(4) Determination of Coefficient of Linear Thermal Expansion (CTE) and Glass Transition Temperature (Tg)" below, the coefficient of linear thermal expansion (CTE) of the cured resin composition of the present invention is preferably 70 ppm / ℃ or less, 60 ppm / ℃ or less, or 55 ppm / ℃ or less, more preferably 50 ppm / ℃ or less, 45 ppm / ℃ or less, or 42 ppm / ℃ or less, further preferably 40 ppm / ℃ or less, 38 ppm / ℃ or less, or 35 ppm / ℃ or less, particularly preferably 32 ppm / ℃ or less, 30 ppm / ℃ or less, or 28 ppm / ℃ or less. There is no particular limitation on the lower limit, and it may be 1 ppm / ℃ or more, or 10 ppm / ℃ or more, etc.

[0451] In one embodiment, the present invention can be implemented by adding (A1) a cyclic ether compound with a four-membered ring or less having cationic polymerization properties and component (D) to a base resin composition containing (A) a cyclic ether compound with a four-membered ring or less, (B) a curing agent, and (C) an inorganic filler, thereby manufacturing the resin composition of the present invention. In this case, compared with the base resin composition, the resin composition of the present invention reduces the dielectric loss tangent of the cured product, particularly the dielectric loss tangent at high temperatures (100°C). That is, the present invention can provide a technique for relatively reducing the dielectric loss tangent of the cured resin composition, particularly a technique for relatively reducing the dielectric loss tangent at high temperatures (100°C).

[0452] As described above, the resin composition of the present invention can produce a cured product exhibiting excellent dielectric loss tangent even at high temperatures (100°C). Therefore, the resin composition of the present invention is preferably used as a resin composition for forming an insulating layer of a printed wiring board (resin composition for insulating layer of printed wiring board), and more preferably as a resin composition for forming an interlayer insulating layer of a printed wiring board (resin composition for interlayer insulating layer of printed wiring board). The resin composition of the present invention is also preferably used when the printed wiring board is a component-integrated circuit board. In addition, the resin composition of the present invention can also be preferably used in semiconductor chip packaging as a resin composition for forming a rewiring layer (resin composition for rewiring layer), that is, as an insulating layer for forming a rewiring substrate of a semiconductor chip package (insulating layer for rewiring substrate). It should be noted that in the present invention, printed wiring boards and rewiring substrates can be collectively referred to as "circuit boards," therefore, the resin composition of the present invention is preferably used as an insulating layer of circuit boards.

[0453] Regarding the resin composition of the present invention, it is also preferred to use it as a resin composition for sealing semiconductor chips (resin composition for semiconductor sealing) in semiconductor chip packaging.

[0454] The resin composition of the present invention can be used in a wide range of applications requiring resin compositions, such as resin sheets, sheet laminates such as prepregs, solder resists, underfill materials, chip bonding materials, hole-filling resins, and component embedding resins.

[0455] [Sheet-like laminated materials (resin sheets, prepregs)]

[0456] The resin composition of the present invention can be used directly or in the form of a sheet-like laminate containing the resin composition.

[0457] As sheet-like laminated materials, resin sheets and prepregs as shown below are preferred.

[0458] In one embodiment, the resin sheet is characterized by comprising a support and a layer of resin composition disposed on the support (hereinafter referred to as the "resin composition layer"), the resin composition layer being formed from the resin composition of the present invention.

[0459] The thickness of the resin composition layer varies depending on the application and can be appropriately determined according to the application. For example, from the viewpoint of thinning printed circuit boards and semiconductor chip packaging, the thickness of the resin composition layer is preferably 200 μm or less, more preferably 150 μm or less, 120 μm or less, 100 μm or less, 80 μm or less, 60 μm or less, or 50 μm or less. There is no particular limitation on the lower limit of the thickness of the resin composition layer, and it can generally be 1 μm or more, 5 μm or more, etc.

[0460] Examples of supports include thermoplastic resin films, metal foils, and release paper, with thermoplastic resin films and metal foils being preferred. Therefore, in a preferred embodiment, the support is a thermoplastic resin film or a metal foil.

[0461] When using a thermoplastic resin film as a support, examples of thermoplastic resins include polyesters such as polyethylene terephthalate (PET) and polyethylene naphthalate (PEN), acrylic resins such as polycarbonate (PC) and polymethyl methacrylate (PMMA), cyclic polyolefins, cellulose triacetate (TAC), polyether sulfide (PES), polyetherketone, and polyimide. Among these, polyethylene terephthalate and polyethylene naphthalate are preferred, and inexpensive polyethylene terephthalate is particularly preferred.

[0462] When using metal foil as a support, examples of metal foils include copper foil and aluminum foil, with copper foil being preferred. As copper foil, foils containing a single metal such as copper can be used, or foils containing alloys of copper with other metals (e.g., tin, chromium, silver, magnesium, nickel, zirconium, silicon, titanium, etc.). Furthermore, in one embodiment, as copper foil, foils composed of a single metal such as copper can be used, or foils composed of alloys of copper with other metals (e.g., tin, chromium, silver, magnesium, nickel, zirconium, silicon, titanium, etc.).

[0463] Regarding the support body, the surface bonded to the resin composition layer can be treated with matte finish, corona treatment, or antistatic treatment. Furthermore, a support body with a release layer on the surface bonded to the resin composition layer can be used. The release agent used in the release layer of the support body with the release layer can be, for example, selected from one or more release agents chosen from alkyd resins, polyolefin resins, urethane resins, and silicone resins. Commercially available release agents include "SK-1," "AL-5," and "AL-7" manufactured by Linkect Co., Ltd. Additionally, commercially available products can be used as the support body with the release layer; for example, PET films having a release layer with an alkyd resin-based release agent as the main component can be represented by "Lumira T60" manufactured by Toray Industries, Ltd., "Purex" manufactured by Teijin Corporation, and "Unipul" manufactured by Unichica Co., Ltd.

[0464] There is no particular limitation on the thickness of the support body, but a range of 5 μm to 75 μm is preferred, and a range of 10 μm to 60 μm is more preferred. It should be noted that when using a support body with a release layer, the overall thickness of the support body with the release layer is preferably within the above-mentioned range.

[0465] When a metal foil is used as a support, a metal foil with a peelable support substrate can be used, in which a thin metal foil is bonded to the support substrate. In one embodiment, the metal foil with a support substrate includes a support substrate, a release layer disposed on the support substrate, and a metal foil disposed on the release layer. When a metal foil with a support substrate is used as a support, a resin composition layer is disposed on the metal foil.

[0466] In metal foils with a support substrate, there are no particular limitations on the material of the support substrate; examples include copper foil, aluminum foil, stainless steel foil, titanium foil, and copper alloy foil. When copper foil is used as the support substrate, it can be electrolytic copper foil or rolled copper foil. Furthermore, regarding the release layer, there are no particular limitations as long as the metal foil can be peeled off from the support substrate; examples include alloy layers selected from elements such as Cr, Ni, Co, Fe, Mo, Ti, W, and P; and organic films.

[0467] In metal foils with a supporting substrate, the preferred material for the metal foil is, for example, copper foil or copper alloy foil.

[0468] In metal foils with a supporting substrate, the thickness of the supporting 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. Additionally, the thickness of the metal foil can, for example, be in the range of 0.1 μm to 10 μm.

[0469] In one embodiment, the resin sheet may further include optional layers as needed. Examples of such optional layers include, for instance, a protective film disposed 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, and is, for example, 1 μm to 40 μm. By laminating the protective films, it is possible to suppress the adhesion of debris and scratches on the surface of the resin composition layer.

[0470] In the case of resin sheets, for example, they can be manufactured by directly applying a liquid resin composition or a resin composition varnish prepared by dissolving the resin composition in an organic solvent onto a support using a molding coater or the like, and then drying it to form a resin composition layer.

[0471] As organic solvents, the same organic solvents described as components of the resin composition in the <(G) Organic Solvents> section can be listed. One organic solvent may be used alone, or two or more may be used in combination.

[0472] Drying can be carried out using known methods such as heating or hot air spraying. There are no particular limitations on the drying conditions; drying is generally carried out when the content of organic solvent in the resin composition layer is 10% by mass or less, preferably 5% by mass or less. Depending 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 10% to 60% by mass of organic solvent, a resin composition layer can be formed by drying at 50°C to 150°C for 3 to 10 minutes.

[0473] Resin sheets can be rolled up and stored. When the resin sheet has a protective film, it can be used by peeling off the protective film.

[0474] In one embodiment, the prepreg is formed by impregnating a sheet fiber substrate with the resin composition of the present invention.

[0475] There are no particular limitations on the sheet fiber substrate used in the prepreg; commonly used sheet fiber 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 chip packaging, the thickness of the sheet fiber substrate is preferably 50 μm or less, more preferably 40 μm or less, further preferably 30 μm or less, and particularly preferably 20 μm or less. There is no particular limitation on the lower limit of the thickness of the sheet fiber substrate. It is usually 10 μm or more.

[0476] Prepregs can be manufactured using known methods such as hot-melt and solvent methods.

[0477] The thickness of the prepreg can be the same range as that of the resin composition layer in the resin sheet described above.

[0478] The sheet-like laminate material of the present invention is preferably used to form an insulating layer for a printed wiring board (for insulating layers of printed wiring boards), and more preferably to form an interlayer insulating layer for a printed wiring board (for interlayer insulating layers of printed wiring boards). The sheet-like laminate material of the present invention is also preferably used to form an insulating layer for a rewiring substrate of a semiconductor chip package (for insulating layers of a rewiring substrate). That is, the sheet-like laminate material of the present invention is preferably used as an insulating layer for a circuit board. The sheet-like laminate material of the present invention is also preferably used to seal semiconductor chips (for semiconductor sealing).

[0479] [Circuit board]

[0480] The resin composition of the present invention can be used to form an insulating layer of a circuit board. The present invention also provides such a circuit board, namely a circuit board comprising an insulating layer having a cured form of the resin composition of the present invention. In one embodiment, the circuit board of the present invention is preferably a circuit board comprising an insulating layer formed of a cured form of the resin composition of the present invention.

[0481] Printed Wiring Board

[0482] In one embodiment, the circuit board of the present invention is a printed wiring board. The printed wiring board of the present invention includes an insulating layer having a cured form of the resin composition of the present invention. In one embodiment, the printed wiring board of the present invention preferably includes an insulating layer composed of a cured form of the resin composition of the present invention.

[0483] Printed wiring boards can be manufactured, for example, using the resin sheet described above, by a method comprising the steps described in (I) and (II) below.

[0484] (I) A process of laminating resin sheets onto an inner substrate such that the resin composition layer of the resin sheets is bonded to the inner substrate.

[0485] (II) The process of heat-curing the resin composition layer to form an insulating layer

[0486] In step (I), resin sheets are laminated onto the inner layer substrate to bond the resin composition layer of the resin sheets to the inner layer substrate. The "inner layer substrate" used in step (I) is a component that becomes the substrate of a printed wiring board; examples include glass epoxy boards, metal substrates, polyester substrates, polyimide substrates, BT resin substrates, and thermosetting polyphenylene ether substrates. Furthermore, this substrate may have a conductor layer on one or both sides, and this conductor layer can be patterned. An inner layer substrate with a conductor layer (circuit) formed on one or both sides of the substrate is sometimes called an "inner layer circuit board." Additionally, intermediate components for which an insulating layer and / or a conductor layer should be formed during the manufacture of the printed wiring board are also included in the "inner layer substrate" as described in this invention. In the case where the printed wiring board is a component-integrated circuit board, an inner layer substrate for integrating the component can be used.

[0487] Regarding the lamination of the inner substrate and the resin sheet, for example, it can be performed by heating and pressing the resin sheet and the inner substrate from the support side. As a component for heating and pressing the resin sheet and the inner substrate (hereinafter also referred to as a "heat-pressing component"), examples include heated metal plates (such as SUS mirror panels) or metal rollers (SUS rollers). It can be explained that the heat-pressing component can be directly pressed onto the resin sheet, or pressure can be applied through an elastic material such as heat-resistant rubber so that the resin sheet fully follows the surface irregularities of the inner substrate.

[0488] The lamination of the inner substrate and the resin sheet can be performed by vacuum lamination. In vacuum lamination, the heating and 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 heating and 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 heating and pressing time is preferably in the range of 10 seconds to 400 seconds, more preferably in the range of 20 seconds to 300 seconds. Lamination is preferably performed under reduced pressure conditions below 26.7 hPa.

[0489] Lamination can be performed using commercially available vacuum laminators. Examples of commercially available vacuum laminators include the vacuum pressurized laminator manufactured by Meiki Seisakusho Co., Ltd., the vacuum booster manufactured by Nikko-materials Co., Ltd., and the intermittent vacuum pressurized laminator.

[0490] After lamination, the laminated resin sheets can be smoothed by applying pressure to the heated pressing members under normal pressure (atmospheric pressure), for example, from the support side. The pressure conditions for smoothing can be set to the same conditions as the heated pressing conditions for lamination described above. The smoothing process can be performed using a commercially available laminator. It should be noted that lamination and smoothing can be performed continuously using the aforementioned commercially available vacuum laminator.

[0491] The support can be removed between steps (I) and (II), or after step (II). It should be noted that if a metal foil is used as the support, the conductor layer can be formed using the metal foil without peeling off the support. Furthermore, if a metal foil with a support substrate is used as the support, only the support substrate (and release layer) needs to be peeled off. Moreover, the conductor layer can be formed using the metal foil.

[0492] In step (II), the resin composition layer is thermally cured to form an insulating layer having the cured resin composition. In one embodiment, it is preferable to thermally cure the resin composition layer in step (II) to form an insulating layer composed of the cured resin composition. There are no particular limitations on the curing conditions of the resin composition layer, and conditions typically used when forming the insulating layer of a printed wiring board can be used.

[0493] For example, the thermosetting conditions of the resin composition layer vary depending on the type of resin composition, etc. In one embodiment, the curing temperature is preferably 120°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 set to 5 minutes to 240 minutes, more preferably 10 minutes to 150 minutes, and even more preferably 15 minutes to 120 minutes.

[0494] Before heat curing the resin composition layer, the resin composition layer may be preheated at a temperature lower than the curing temperature. For example, before heat curing the resin composition layer, it may be preheated at a temperature of 50°C to 120°C, preferably 60°C to 115°C, more preferably 70°C to 110°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.

[0495] In manufacturing a printed wiring board, steps (III) of drilling holes in the insulating layer, (IV) of roughening the insulating layer, and (V) of forming the conductor layer can be further performed. These steps (III) to (V) can be performed according to various methods known to those skilled in the art and used in the manufacture of printed wiring boards. It should be noted that if the support is removed after step (II), the removal of the support can be performed between steps (II) and (II I), between steps (III) and (IV), or between steps (IV) and (V). Furthermore, as needed, the formation of the insulating and conductor layers in steps (I) to (V) can be repeated to form a multilayer wiring board.

[0496] In another embodiment, the printed wiring board of the present invention can be manufactured using the prepreg described above. The manufacturing method is essentially the same as that used with resin sheets.

[0497] Step (III) is the drilling process for the insulating layer, thereby forming through holes, through-holes, and other holes in the insulating layer. Step (III) can be performed using, for example, a drill bit, laser, plasma, or other methods, depending on the composition of the resin composition used in the formation of the insulating layer. The size and shape of the holes can be appropriately determined according to the design of the printed circuit board.

[0498] Step (IV) is the process of roughening the insulation layer. Typically, stain removal is also performed in this step (IV). There are no particular limitations on the steps or conditions of the roughening process; commonly used and known steps and conditions can be used when forming the insulation layer of the printed circuit board. For example, the insulation layer can be roughened sequentially by performing a swelling treatment using a swelling solution, a roughening treatment using an oxidizing agent, and a neutralization treatment using a neutralizing solution.

[0499] The swelling solution used for roughening treatment is not particularly limited, and examples include alkaline solutions and surfactant solutions. An alkaline solution is preferred, and sodium hydroxide solution or potassium hydroxide solution is more preferred. Commercially available swelling solutions include, for example, "Swelling Disc Securitization P" and "Swelling Disc Securitization SBU" manufactured by Attec Japan Co., Ltd. The swelling treatment using a swelling solution is not particularly limited; for example, it can be performed 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 in the insulating layer to a moderate level, it is preferable to immerse the insulating layer in a swelling solution at 40°C to 80°C for 5 to 15 minutes.

[0500] The oxidant used for roughening is not particularly limited; for example, an alkaline permanganate solution in which potassium permanganate or sodium permanganate is dissolved in an aqueous solution of sodium hydroxide can be cited. For roughening treatment using an oxidant such as an alkaline permanganate solution, it is preferable to immerse the insulating layer in an oxidant 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 "Contronic CP" and "Contronic CP" manufactured by Atotron Corporation. Alkaline permanganic acid solutions such as "コンセントレート·コンパクトP" and "ドージングソリューション·セキュリガンスP".

[0501] In addition, an acidic aqueous solution is preferred as the neutralizing liquid used for roughening treatment. As a commercially available product, examples include "Reducing Solution Sequential P" manufactured by Attic Japan Co., Ltd.

[0502] Regarding the treatment using a neutralizing solution, it can be performed by immersing the surface roughened with an oxidant in a neutralizing solution at 30°C to 80°C for 5 to 30 minutes. From the perspective of workability, it is preferable to immerse the roughened object with an oxidant in a neutralizing solution at 40°C to 70°C for 5 to 20 minutes.

[0503] Step (V) is the step of forming a conductor layer, which is formed on the insulating layer. There are no particular limitations on the conductor material used in the conductor layer. In a preferred embodiment, the conductor layer comprises one or more metals selected from gold, platinum, palladium, silver, copper, aluminum, cobalt, chromium, zinc, nickel, titanium, tungsten, iron, tin, and indium. The conductor layer can be a single metal layer or an alloy layer. Examples of alloy layers include layers formed from alloys of two or more metals selected from the above group (e.g., nickel-chromium alloys, copper-nickel alloys, and copper-titanium alloys). From the viewpoint of versatility, cost, and ease of patterning in conductor layer formation, single metal layers of chromium, nickel, titanium, aluminum, zinc, gold, palladium, silver, or copper, or alloy layers of nickel-chromium alloys, copper-nickel alloys, or copper-titanium alloys, are preferred. Single metal layers of chromium, nickel, titanium, aluminum, zinc, gold, palladium, silver, or copper, or alloy layers of nickel-chromium alloys, are more preferred. A single metal layer of copper is even more preferred.

[0504] The conductor layer can be a single-layer structure or a multilayer structure consisting of two or more single-metal layers or alloy layers of different types of metals or alloys. In one embodiment, the conductor layer can be a single-layer structure or a multilayer structure consisting of two or more single-metal layers or alloy layers of different types of metals or alloys. When the conductor layer is a multilayer structure, it is preferable that the layer in contact with the insulating layer is a single-metal layer of chromium, zinc, or titanium, or an alloy layer of nickel-chromium alloy.

[0505] The thickness of the conductor layer depends on the design of the required printed wiring board, and is generally 3μm to 35μm, preferably 5μm to 30μm.

[0506] In one embodiment, the conductor layer can be formed by plating. For example, conventionally known techniques such as semi-additive and fully additive methods can be used to plate the surface of the insulating layer to form a conductor layer with the desired wiring pattern. From the viewpoint of ease of manufacturing, the semi-additive method is preferred. Hereinafter, an example of forming the conductor layer using the semi-additive method is shown.

[0507] First, a plating seed layer is formed on the surface of the insulating layer by chemical plating. Second, a mask pattern is formed on the formed plating seed layer, corresponding to the desired wiring pattern, exposing a portion of the plating seed layer. After a metal layer is formed on the exposed plating seed layer by electroplating, the mask pattern is removed. Then, the unwanted plating seed layer is removed by etching or the like, thus forming a conductor layer with the desired wiring pattern.

[0508] In another embodiment, the conductor layer can be formed using metal foil. When using metal foil to form the conductor layer, step (V) is preferably performed between steps (I) and (II). For example, after step (I), the support is removed, and metal foil is laminated onto the surface of the exposed resin composition layer. The lamination of the resin composition layer and the metal foil can be performed using vacuum lamination. The lamination conditions can be the same as those described for step (I). Next, step (II) is performed to form an insulating layer. Then, using the metal foil on the insulating layer, a conductor layer with the desired wiring pattern can be formed using existing known techniques such as subtractive processing or modified semi-additive processing.

[0509] Metal foils can be manufactured using known methods such as electrolysis and rolling. Commercially available metal foils include, for example, "HLP foil" and "JXUT-III foil" manufactured by JX Metals Corporation, and "3EC-III foil" and "TP-III foil" manufactured by Mitsui Metals & Mining Corporation.

[0510] Alternatively, as a support for the resin sheet, the metal foil can be used to form a conductor layer when a metal foil with a supporting substrate is used, as described above.

[0511] <Rewiring substrate for semiconductor chip packaging>

[0512] In one embodiment, the circuit board of the present invention is a rewiring board for semiconductor chip packaging. Hereinafter, a method for manufacturing semiconductor chip packaging will be described.

[0513] [Semiconductor chip packaging]

[0514] The semiconductor chip package of the present invention includes a sealing layer having a cured form of the resin composition of the present invention. In one embodiment, the semiconductor chip package of the present invention preferably includes a sealing layer formed of a cured form of the resin composition of the present invention. The semiconductor chip package of the present invention may further include, as described above, an insulating layer (rewiring layer) of a rewiring substrate having a cured form of the resin composition of the present invention. The semiconductor chip package of the present invention may further include an insulating layer (rewiring layer) of a rewiring substrate formed of a cured form of the resin composition of the present invention.

[0515] In the case of semiconductor chip packaging, for example, the resin composition and resin sheet of the present invention can be used to manufacture the package by a method comprising the steps (1) to (6) described below. The resin composition and resin sheet of the present invention can be used to form the sealing layer of step (3) or the rewiring layer of step (5). Hereinafter, an example of forming the sealing layer and rewiring layer using the resin composition and resin sheet is shown; however, the techniques for forming the sealing layer and rewiring layer of a semiconductor chip package are well known, and those skilled in the art can use the resin composition and resin sheet of the present invention to manufacture a semiconductor package according to known techniques.

[0516] (1) The process of temporarily fixing the film in the substrate lamination,

[0517] (2) The process of temporarily fixing the semiconductor chip on a temporary fixing film.

[0518] (3) The process of forming a sealing layer on a semiconductor chip.

[0519] (4) The process of peeling the substrate and temporary fixing film from the semiconductor chip.

[0520] (5) The process of forming a rewiring layer as an insulating layer on the surface of a semiconductor chip where the substrate and temporary fixing film are peeled off, and

[0521] (6) The process of forming a rewiring layer as a conductor layer on the rewiring forming layer.

[0522] <Process (1)>

[0523] There are no particular limitations on the materials used as substrates. Examples of substrates include silicon wafers; glass wafers; glass substrates; metal substrates such as copper, titanium, stainless steel, and cold-rolled steel sheet (SPCC); substrates impregnated with epoxy resin or the like in glass fibers and heat-cured (e.g., FR-4 substrates); and bismaleimide triazine resin (BT resin) substrates. In one embodiment, the maleimide triazine resin (BT resin) substrate is a substrate made of bismaleimide triazine resin (BT resin).

[0524] Regarding the temporary fixing film, there are no particular limitations on the material, as long as it can be peeled off from the semiconductor chip in process (4) and temporarily fixed at the same time. Commercially available products can be used for the temporary fixing film. Examples of commercially available products include Rivaalfa manufactured by Nitto Denko Corporation.

[0525] <Process (2)>

[0526] Temporary bonding of semiconductor chips can be performed using known devices such as flip-chip bonding machines and chip bonding machines. Regarding the configuration design and number of semiconductor chips, the configuration can be appropriately set according to the shape and size of the temporary bonding film, the production quantity of the target semiconductor package, etc. For example, it can be integrated into a multi-row, multi-column matrix for temporary bonding.

[0527] <Process (3)>

[0528] A sealing layer is formed by laminating the resin composition layer of the resin sheet of the present invention onto a semiconductor chip, or by coating and curing (e.g., thermosetting) the resin composition of the present invention onto a semiconductor chip.

[0529] For example, the lamination of a semiconductor chip and a resin sheet can be performed by removing the protective film from the resin sheet and then heating and pressing the resin sheet onto the semiconductor chip from the support side. As a component for heating and pressing the resin sheet onto the semiconductor chip (hereinafter also referred to as a "heat-pressing component"), examples include heated metal plates (such as SUS mirror panels) or metal rollers (SUS rollers). It should be noted that it is preferable not to directly press the resin sheet onto the heat-pressing component, but rather to press it through an elastic material such as heat-resistant rubber so that the resin sheet fully conforms to the surface irregularities of the semiconductor chip. The lamination of the semiconductor chip and the resin sheet can be carried out by vacuum lamination, 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.

[0530] After lamination, the resin composition is thermosetting to form a sealing layer. The thermosetting conditions are the same as those described in relation to the manufacturing method of the printed wiring board.

[0531] Regarding the support for the resin sheet, the resin sheet can be laminated on the semiconductor chip and then peeled off after thermosetting, or the support can be peeled off before the resin sheet is laminated on the semiconductor chip.

[0532] When a sealing layer is formed by coating the resin composition of the present invention, the coating conditions are the same as those described in relation to the resin sheet of the present invention for forming a resin composition layer, and the preferred range is also the same.

[0533] <Process (4)>

[0534] Regarding the method of peeling the substrate and the temporary fixing film, it can be appropriately changed according to the material of the temporary fixing film. For example, methods such as heating, foaming (or expanding) the temporary fixing film to peel it off, and irradiating the substrate side with ultraviolet light to reduce the adhesive force of the temporary fixing film to peel it off, can be listed.

[0535] In methods that peel off a temporary fixing film by heating, foaming (or expanding), the heating conditions are typically 100–250°C for 1–90 seconds or 5–15 minutes. Conversely, in methods that peel off a temporary fixing film by irradiating it with ultraviolet light from the substrate side to reduce its adhesive strength, the ultraviolet radiation dose is typically 10 mJ / cm². 2 ~1000mJ / cm 2 .

[0536] <Process (5)>

[0537] Regarding the materials used to form the rewiring layer (insulating layer), there are no particular limitations as long as they possess insulating properties during the formation of the rewiring layer (insulating layer). From the viewpoint of ease of manufacturing semiconductor chip packages, ultraviolet-curable resins and thermosetting resins are preferred. The resin compositions and resin sheets of the present invention can be used to form the rewiring layer.

[0538] After the rewiring layer is formed, vias can be formed in the rewiring layer to enable interlayer connections between the semiconductor chip and the conductor layer described later. The vias can be formed using known methods depending on the material of the rewiring layer.

[0539] <Process (6)>

[0540] Regarding the formation of the conductor layer on the rewiring forming layer, it can be performed in the same manner as step (V) described in relation to the manufacturing method of the printed wiring board. It should be noted that steps (5) and (6) can be performed repeatedly to alternately stack (assemble) the conductor layer (rewiring layer) and the rewiring forming layer (insulating layer).

[0541] In the manufacture of semiconductor chip packages, the following steps may be performed: (7) forming a solder mask layer on the conductor layer (rewiring layer); (8) forming bumps; and (9) dicing multiple semiconductor chip packages into individual semiconductor chip packages for chip-to-chip processing. These steps may be performed according to various methods known to those skilled in the art and used in the manufacture of semiconductor chip packages.

[0542] By using the resin composition and resin sheet of the present invention, which produce a cured product exhibiting excellent dielectric properties, to form a sealing layer and a rewiring layer, a semiconductor chip package with extremely low transmission loss can be achieved regardless of whether the semiconductor package is a fan-in or fan-out package. In one embodiment, the semiconductor chip package of the present invention is a fan-out package. The resin composition and resin sheet of the present invention can be used for both fan-out panel-level package (FO-PLP) and fan-out wafer-level package (FO-WLP). In one embodiment, the semiconductor package of the present invention is a fan-out panel-level package (FOPLP). In another embodiment, the semiconductor package of the present invention is a fan-out wafer-level package (FOWLP).

[0543] [Semiconductor Devices]

[0544] The semiconductor device of the present invention comprises a layer having a cured form of the resin composition of the present invention, and includes a circuit board or semiconductor chip package of the present invention. In one embodiment, the semiconductor device of the present invention preferably comprises a layer formed of a cured form of the resin composition of the present invention.

[0545] As semiconductor devices, various semiconductor devices supplied to electrical products (such as computers, mobile phones, digital cameras and televisions) and transportation vehicles (such as motorcycles, automobiles, trams, ships and aircraft) can be listed.

[0546] Example

[0547] The present invention will be described in more detail below using examples, but the present invention is not limited to these examples. It should be noted that, unless otherwise expressly stated, "parts" and "%" refer to "parts by mass" and "% by mass," respectively.

[0548] <Preparation of Resin Composition (Resin Varnish)>

[0549] Each component was weighed according to the mass fractions listed in Tables 1 and 2, and uniformly dispersed using a high-speed rotary mixer to obtain a resin composition (resin varnish). Specifically, among the components listed in Tables 1 and 2, firstly, components (A2), (B), (C), (E), (F), (G), (H), and (I) were mixed to prepare resin composition (i). Secondly, resin composition (i), component (A1), and component (D) were mixed to obtain resin composition (ii).

[0550] [Table 1]

[0551] Table 1

[0552]

[0553] [Table 2]

[0554] Table 2

[0555]

[0556] The details of each component recorded in Tables 1 and 2 are as follows.

[0557] (A1)Ingredients

[0558] • Limonene dioxide: Cationic polymeric epoxy resin (functional group equivalent 96 g / eq., manufactured by Cargill).

[0559]

Chemistry 17

[0560]

[0561] •Cerokise 2021P: Cationic polymeric epoxy resin (functional group equivalent 120g / eq., manufactured by Daicel Corporation)

[0562] [Chemistry 18]

[0563]

[0564] EHPE3150: Cationic polymeric epoxy resin (functional group equivalent 180 g / eq., manufactured by Daicel Corporation)

[0565]

Chemistry 19

[0566]

[0567] (In the formula, n1, n2, and n3 each independently represent integers greater than or equal to 0.)

[0568] • OXT-221: Cationic polymerizable oxetane resin (functional group equivalent 107 g / eq., manufactured by Toa Synthetic Co., Ltd.)

[0569]

Chemistry 20

[0570]

[0571] (A2) Ingredients

[0572] ·828EL: Bisphenol A type epoxy resin (epoxy equivalent 180g / eq., manufactured by Mitsubishi Chemical Corporation)

[0573] HP-4032SS: Naphthalene-type epoxy resin (epoxy equivalent 144g / eq. manufactured by DIC).

[0574] NC3000L: Biphenyl-type epoxy resin (epoxy equivalent 269 g / eq., manufactured by Nippon Kayaku Co., Ltd.)

[0575] YX4000HK: Bis(xylenol) type epoxy resin (epoxy equivalent 185 g / eq., manufactured by Mitsubishi Chemical Corporation)

[0576] • ESN475V: Naphthalene-type epoxy resin (epoxy equivalent 332 g / eq., manufactured by Nippon Steel Kemical & Materia Co., Ltd.)

[0577] HP-6000: Naphthalene ether type epoxy resin (epoxy equivalent 250g / eq., manufactured by DIC).

[0578] HP-7200HH: Dicyclopentadiene type epoxy resin (epoxy equivalent 283g / eq., manufactured by DIC).

[0579] (B) Ingredients

[0580] HPC-8000-65T: An active ester-based curing agent containing a dicyclopentadiene-type diphenol structure (functional group equivalent 223 g / eq., toluene solution with 65% by mass of non-volatile components, manufactured by DIC).

[0581] HPC-8150-62T: Naphthalene-type reactive ester curing agent (functional group equivalent 223 g / eq., toluene solution with 62% by mass of non-volatile components, manufactured by DIC Company)

[0582] LA-3018-50P: A phenolic curing agent containing a triazine skeleton (phenolic varnish resin containing a triazine skeleton) (a propylene glycol monomethyl ether (1-methoxy-2-propanol) solution with a functional group equivalent of 151 g / eq. and a non-volatile component percentage of 50% by mass, manufactured by DIC).

[0583] V-03: Carbodiimide-based curing agent (toluene solution with a functional group equivalent of 216 g / eq. and a non-volatile component content of 50% by mass, manufactured by Nisshinbo Kemikal Co., Ltd.)

[0584] (C) Components

[0585] • SO-C2 (with surface treatment): Spherical silica (average particle size 0.5 μm, specific surface area 5.8 m²) surface-treated with an amine-based silane coupling agent (N-phenyl-3-aminopropyltrimethoxysilane, Shin-Etsu Chemical Industry Co., Ltd. "KBM-573") 2 / g, Made by Atomtec Co., Ltd.)

[0586] SO-C2: Spherical silica (average particle size 0.5 μm, specific surface area 5.8 m²) 2 / g, Made by Atomtec Co., Ltd.)

[0587] •ASFP-40: Spherical alumina (average particle size 0.4 μm, specific surface area 6.3 m²) surface-treated with an amine-based silane coupling agent (N-phenyl-3-aminopropyltrimethoxysilane, Shin-Etsu Chemical Industry Co., Ltd. "KBM-573") 2 / g, Made by Denka Corporation)

[0588] UFP-30: Spherical silica (average particle size 0.3 μm, specific surface area 30.7 m²) surface-treated with an amine-based silane coupling agent (N-phenyl-3-aminopropyltrimethoxysilane, Shin-Etsu Chemical Industry Co., Ltd. "KBM-573") 2 / g, Made by Denka Corporation)

[0589] • FB-5SDC: Spherical silica (average particle size 4.1 μm, specific surface area 2.1 m²) surface-treated with amine-based silane coupling agent (N-phenyl-3-aminopropyltrimethoxysilane, Shin-Etsu Chemical Industry Co., Ltd. "KBM-573") 2 / g, Made by Denka Corporation)

[0590] (D) Components

[0591] • Aluminum chelate D: Monoacetylacetone bis(ethyl acetoacetate)aluminum (76% by mass of non-volatile component in 2-propanol solution, manufactured by Kawaken Fin Chemical Co., Ltd.)

[0592] ·AMD: Aluminum diisopropoxymono-sec-butoxide (アルミニウムジイソプロピレートモノsec-ブチレート) (manufactured by Kawayan Chemical Co., Ltd.)

[0593] (E) Components

[0594] MIR-3000-70MT: Biphenyl arylphenolic varnish type maleimide resin (MEK / toluene mixed solution with 70% by mass of non-volatile components, manufactured by Nippon Kayaku Co., Ltd.)

[0595] • BMI-1500: A polyimide resin containing a dimerized diamine structure with maleimide groups at the ends (manufactured by Designer Molecules Inc.)

[0596] • OPE-2St 2200: Vinyl benzyl modified polyphenylene ether resin (toluene solution with 65% by mass of non-volatile components, manufactured by Mitsubishi Gas Chemical Co., Ltd.)

[0597] (F)Ingredients

[0598] • DMAP: Amine-based curing accelerator (4-dimethylaminopyridine, manufactured by Tokyo Chemical Industry Co., Ltd.)

[0599] ·1B2PZ: Imidazole-based curing accelerator (1-benzyl-2-phenylimidazolium, manufactured by Shikoku Chemical Industry Co., Ltd.)

[0600] (G) component

[0601] • Staphiroide AC3816N: Acrylic core-shell rubber particles (manufactured by Iika Industrial Co., Ltd.)

[0602] (H) component

[0603] YX7553BH30: Phenoxy resin (a 1:1 solution of MEK and cyclohexanone with a non-volatile content of 30% by mass, manufactured by Mitsubishi Chemical Corporation)

[0604] <Characteristic Evaluation>

[0605] (1) Fabrication of resin sheets with a resin composition layer thickness of 40 μm

[0606] As a support, a polyethylene terephthalate film (38 μm thick) treated with an alkyd resin release agent (Lintec "AL-5") was prepared. The resin composition (resin varnish) obtained in the examples and comparative examples was uniformly applied onto the release layer of this support so that the thickness of the dried resin composition layer was 40 μm. The resin composition was then dried at 80°C to 100°C (average 90°C) for 2 minutes to obtain a resin sheet comprising the support and the resin composition layer.

[0607] (2) Preparation of cured resin composition layer

[0608] The prepared resin sheet was cured in an oven at 190°C for 90 minutes. The support was peeled off by removing the resin sheet from the oven, yielding a cured resin composition layer.

[0609] (3) Determination of dielectric loss tangent (dielectric properties)

[0610] The cured resin composition layer was cut into 80mm and 2mm pieces. The dielectric loss tangent (Df value) was measured using an Agilent Technologies HP8362B instrument at a measurement frequency of 5.8 GHz and measurement temperatures of 23°C and 100°C. Measurements were performed on two test pieces, and the average value was calculated. The results were evaluated according to the following criteria. Furthermore, the difference between the dielectric loss tangent at 100°C and 23°C was calculated.

[0611] • Dielectric loss tangent measured at 23°C

[0612] ○: Dielectric loss tangent (23℃) is below 0.0044.

[0613] ×: Dielectric loss tangent (23℃) is greater than 0.0044.

[0614] • Dielectric loss tangent measured at 100℃

[0615] ○: Dielectric loss tangent (100℃) is below 0.0050°.

[0616] ×: Dielectric loss tangent (100℃) is greater than 0.0050.

[0617] • The difference between the dielectric loss tangent measured at 100℃ and the dielectric loss tangent measured at 23℃

[0618] ○: The difference in dielectric loss tangent (100℃-23℃) is below 0.0009.

[0619] ×: The difference in dielectric loss tangent (100℃-23℃) is greater than 0.0009.

[0620] (4) Determination of linear thermal expansion coefficient (CTE) and glass transition temperature (Tg)

[0621] The cured resin composition layer was cut into test pieces approximately 15 mm in length and 5 mm in width. Thermomechanical analysis was performed using a thermomechanical analysis apparatus (Thermo Plus TMA8310, manufactured by Rigaku Corporation) using the tensile loading method. Specifically, the test pieces were mounted on the apparatus and measured twice consecutively under a load of 1 g and a heating rate of 5 °C / min. The first measurement was heated to 200 °C, and the second to 260 °C. In the second measurement, the average linear thermal expansion coefficient (CTE) and glass transition temperature (Tg) in the planar direction from 25 °C to 150 °C were calculated.

[0622] As shown in Tables 1 and 2, in Examples 1 to 17, which contain a cyclic ether compound with a four-membered ring or less (A), a curing agent, an inorganic filler, and component (D) as specified in this application, and whose component (A) includes a cyclic ether compound with a four-membered ring or less that has cationic polymerization properties (A1), cured products exhibiting excellent dielectric loss tangents can be obtained even at high temperatures (100°C). However, in Comparative Example 1 (without component (D)) and Comparative Example 2 (without component (A1)), the dielectric loss tangent values ​​at high temperatures (100°C) are high and not satisfactory.

Claims

1. A resin composition, which is a resin composition containing: (A) a cyclic ether compound having four or fewer rings, (B) a curing agent, (C) an inorganic filler, and (ID) an aluminum complex. (A) The component (A) contains (Al) a cyclic ether compound having cationic polymerizability.

2. A resin composition, which is a resin composition containing: (A) a cyclic ether compound having four or fewer rings, (B) a curing agent, (C) an inorganic filler, (2D-1) aluminum, and (2D-2) an organic ligand having an oxygen atom as a coordinating atom. (A) The component (A) contains (Al) a cyclic ether compound having cationic polymerizability. (A) The component (A) further contains a component (A2) which is a cyclic ether compound having four or fewer rings other than the component (Al). wherein, The content of the component (Al) is 0.1 to 6.0 mass% when the nonvolatile components in the resin composition are taken as 100 mass%. The content of the component (C) is 50 mass% or more when the nonvolatile components in the resin composition are taken as 100 mass%. The content of the component (ID) is 0.01 to 0.20 mass% when the nonvolatile components in the resin composition are taken as 100 mass%. The total of the content of the component (2D-1) and the component (2D-2) is 0.01 to 0.20 mass% when the nonvolatile components in the resin composition are taken as 100 mass%. The component (Al) contains an alicyclic epoxy resin. The component (A2) contains an aromatic epoxy resin. The component (B) contains an active ester-based curing agent. wherein The component (C) contains an inorganic oxide.

3. The resin composition according to claim 1 or 2, wherein, The component (C) contains silica.

4. The resin composition according to claim 1 or 2, wherein, The average particle diameter of the component (C) is 5.0 μm or less.

5. The resin composition according to claim 1 or 2, wherein, The component (ID) contains an aluminum chelate complex.

6. The resin composition according to claim 1, wherein, The component (ID) contains one or more kinds of aluminum complexes selected from the group consisting of an aluminum complex having an alkoxide as a ligand, an aluminum complex having a β-diketone enolate as a ligand, and an aluminum complex having a β-ketoate enolate as a ligand.

7. The resin composition according to claim 2, wherein, The component (2D-1) contains an aluminum ion.

8. The resin composition according to claim 1 or 2, wherein, The component (2D-2) contains one or more kinds of organic ligands selected from the group consisting of an alcohol, an alkoxide, a β-diketone, a β-diketone enolate, a β-ketoate, and a β-ketoate enolate.

9. The resin composition according to claim 3, wherein, 19. The resin composition according to claim 1 or 2, further containing (E) a radical-curable resin.

10. The resin composition according to claim 1 or 2, wherein, 20. The resin composition according to claim 1 or 2, further containing (F) a curing accelerator.

11. The resin composition according to claim 1 or 2, wherein, 21. The resin composition according to claim 1 or 2, further containing (G) an organic filler.

12. The resin composition according to claim 1 or 2, wherein, 22. The resin composition according to claim 1 or 2, further containing (H) a thermoplastic resin.

13. The resin composition according to claim 1 or 2, wherein, The cured product of the resin composition has a dielectric loss tangent (Df) of 0.0050 or less when measured at 5.8 GHz and 100°C.

14. The resin composition according to claim 1 or 2, wherein, (C) the specific surface area of the component is 0.1 to 50 m 2 / g.

15. The resin composition according to claim 1, wherein, 24. The resin composition according to claim 1 or 2, which is used for an insulating layer of a circuit substrate.

16. The resin composition according to claim 1, wherein, 25. The resin composition according to claim 1 or 2, which is used for semiconductor sealing.

17. The resin composition according to claim 2, wherein, ​ 18. The resin composition according to claim 2, wherein, ​ ​ ​ ​ ​ 23. The resin composition according to claim 1 or 2, wherein, ​ ​ ​ 26. A resin sheet comprising: a support body, and a layer of the resin composition according to claim 1 or 2 provided on the support body.

27. The resinous sheet of claim 26, wherein, The support body is a thermoplastic resin film or a metal foil.

28. A prepreg produced by impregnating a sheet-like fibrous base material with the resin composition according to claim 1 or 2.

29. A cured product of the resin composition according to claim 1 or 2.

30. A circuit substrate comprising: an insulating layer having a cured product of the resin composition according to claim 1 or 2.

31. A semiconductor chip package comprising: a sealing layer having a cured product of the resin composition according to claim 1 or 2.

32. The semiconductor chip package according to claim 31, which is a Fan-Out type package.

33. A semiconductor device comprising the circuit substrate according to claim 30.

34. A semiconductor device comprising the semiconductor chip package according to claim 31.

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