resin composition

Abstract

The present invention provides a resin composition that can produce a cured product with low dielectric loss tangent, good crack resistance, and suppressed plating penetration. [Solution] A resin composition comprising (A) a compound containing one or more 2,2,6,6-tetramethylpiperidine-1-oxyl structures in its molecule, (B) an inorganic filler, (C) a maleimide resin, and (D) a vinyl resin having a specific structure.

Description

[Technical Field]

[0001] The present invention relates to a resin composition and a resin sheet, circuit board, and semiconductor device obtained using the resin composition. [Background technology]

[0002] With increasing communication speeds, insulating materials for circuit boards require insulating materials with excellent dielectric properties (low dielectric constant, low dielectric loss tangent) to reduce transmission loss when operating in high-frequency environments. To lower the dielectric loss tangent, it is effective to include a component that lowers the dielectric loss tangent in the resin composition. Radical polymerizable resins (vinyl resins) having a vinyl structure are known as components that lower the dielectric loss tangent, and for example, resin compositions containing vinyl benzyl-modified polyphenylene ether resin or methacrylic-modified polyphenylene ether resin are known (Patent Document 1). However, in resin compositions containing vinyl resin, the effects of thermal oxidative degradation due to heating during curing are significant, which can lead to problems such as an increase in dielectric constant and dielectric loss tangent, as well as a decrease in adhesion between the insulating layer and the conductive layer (copper foil). Furthermore, when inorganic fillers are combined and formulated to improve the thermal expansion coefficient and dielectric properties of the insulating layer, a problem may arise in the plating process after roughening treatment where the plated conductor penetrates into the interior of the insulating layer along the interface between the inorganic filler and the resin component near the surface of the insulating layer (hereinafter also referred to as "penetration"). With the increasing performance of electronic devices, the finer wiring of circuit boards is progressing, and the line-and-space (L / S) ratio of circuits is tending to decrease. Coupled with these technological trends, if penetration occurs, there is a concern that the circuit may short-circuit. Resin compositions containing organic radical compounds such as TEMPO have been reported to control the progression of radical polymerization in maleimide resins and the like (Patent Document 2). [Prior art documents] [Patent Documents]

[0003] Patent Document 1 Japanese Unexamined Patent Publication No. 2021-161325 Patent Document 2 International Publication No. 2020 / 158849 Summary of Invention Problem to be Solved by the Invention

[0004] An object of the present invention is to provide a resin composition with reduced dielectric loss tangent, excellent crack resistance in desmear treatment, and suppressed plating intrusion, a resin sheet using the resin composition, a circuit board comprising a cured product of the resin composition, and a semiconductor device comprising the circuit board. Means for Solving the Problem

[0005] As a result of intensive studies, the present inventors have found that the above object can be achieved by a resin composition having the following constitution, and have completed the present invention. That is, the present invention includes the following aspects.

[0006] [1] A resin composition comprising (A) a compound containing one or more 2,2,6,6-tetramethylpiperidin-1-oxyl structures in the molecule, (B) an inorganic filler, (C) a maleimide resin, and (D) a vinyl resin having a specific structure, the component (D) is (D-1) a vinyl resin containing a structural unit represented by the following formula (D1-1) and a terminal group represented by the following formula (y), (D-2) a vinyl resin containing a structural unit represented by the following formula (D2-1) and a terminal group represented by the following formula (y), and (D-3) a resin selected from the group consisting of vinyl resins containing a radically polymerizable group having a vinyl structure and an active ester moiety. [Chemical Formula] (In formula (D1-1), R1 each independently represents a divalent nitrogen-containing heteroaromatic group which may have a substituent, R 2 each independently represents a divalent organic group, X 1 each independently represents -O-, -S-, or -N(R 3 )-, R 3 represents a hydrogen atom, a monovalent hydrocarbon group having 1 to 20 carbon atoms, a monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms, or a group in which a part of the hydrocarbon group or the halogenated hydrocarbon group is substituted with at least one selected from an oxygen atom and a sulfur atom.)

Chemical Formula

Chemical Formula

Chemical Formula

Chemical Formula

Chemical Formula

[10] The resin composition according to any one of [1] to [9], wherein the group represented by Y in formula (y) contains a monovalent aromatic group containing a radical polymerizable group.

[11] The resin composition according to any one of [1] to [9], wherein the group represented by Y in formula (y) is a vinylbenzyl group.

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

[11] , wherein the content of component (B) is 60% by mass or more relative to 100% by mass of nonvolatile components in the resin composition.

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

[12] , further comprising (E) a curing accelerator.

[14] The resin composition according to

[13] , wherein component (E) is a curing accelerator selected from the group consisting of imidazole curing accelerators, benzotriazole curing accelerators, tetrazole curing accelerators, peroxide radical polymerization initiators, and azo radical polymerization initiators.

[15] The resin composition according to

[13] , wherein component (E) is an imidazole-based curing accelerator.

[16] A resin composition according to any one of [1] to

[15] , further comprising (F) a thermosetting monomer.

[17] The resin composition according to

[16] , wherein component (F) contains a cyclic structure.

[18] The resin composition according to

[16] , wherein component (F) contains one or more functional groups selected from the group consisting of vinyl groups, allyl groups, (meth)acryloyl groups, and amino groups.

[19] The resin composition according to

[16] , wherein component (F) is a benzoxazine resin.

[20] The resin composition according to [1] further comprising (G) an organic filler.

[21] The resin composition according to [1] further comprising (H) a thermoplastic resin.

[22] A resin sheet comprising a support and a resin composition layer formed on the support, wherein the resin composition layer contains the resin composition described in any one of [1] to

[21] .

[23] A circuit board comprising a cured product of any one of the resin compositions described in [1] to

[21] .

[24] A semiconductor device including the circuit board described in

[23] .

[25] A method for manufacturing a circuit board, comprising the following steps (I) to (V). (I) A step of laminating the resin sheet described in

[22] onto the inner layer substrate such that the resin composition layer of the resin sheet and the inner layer substrate are bonded together. (II) A step of curing the resin composition layer to form an insulating layer, (III) A step of forming holes in the insulating layer, (IV) A process of applying desmear treatment to the insulating layer. (V) Step of forming a conductive layer on the surface of the insulating layer after desmearing.

[26] (I) A step of laminating a resin sheet onto an inner layer substrate such that the resin composition layer of the resin sheet and the inner layer substrate are bonded together. (II) A step of curing the resin composition layer to form an insulating layer, (III) A step of forming holes in the insulating layer, (IV) A process of applying desmear treatment to the insulating layer. (V) The resin sheet according to

[22] for use in a method for manufacturing a circuit board, which includes a step of forming a conductive layer on the surface of an insulating layer after desmearing. [Effects of the Invention]

[0007] According to the present invention, it is possible to provide a resin composition in which the dielectric loss tangent is reduced, the crack resistance of the desmear treatment is good, and plating penetration is suppressed; a resin sheet using the resin composition; a circuit board containing a cured product of the resin composition; and a semiconductor device containing the circuit board. [Modes for carrying out the invention]

[0008] The present invention will be described below with reference to embodiments and examples. However, the present invention is not limited to the embodiments and examples shown below, and may be modified and implemented without departing from the scope of the claims and their equivalents.

[0009] [Explanation of terms] The embodiments described herein may be used in combination with each other, regardless of expressions such as "preferred" or "more preferred." For example, the numerical range may be described using the upper and lower limits of each range, as well as a range combining the numerical values ​​of the examples.

[0010] In this specification, "non-volatile components" as used with respect to a resin composition refers to components of the resin composition other than the organic solvents (J) described later.

[0011] In this specification, the term "may have substituents" when referring to a compound or group means, unless otherwise specified, both cases where the hydrogen atoms of the compound or group are not substituted by substituents, and cases where some or all of the hydrogen atoms of the compound or group are substituted by substituents. Furthermore, when the number of constituent atoms of a compound or group is stated, unless otherwise specified, the number of constituent atoms of substituents is not included. Furthermore, when the number of carbon atoms of a compound or group is stated, unless otherwise specified, the number of carbon atoms of substituents is not included.

[0012] In this specification, "aromatic ring" means a ring that obeys Hückel's rule, in which the number of electrons in the π-electron system on the ring is 4r+2 (where r is a natural number greater than or equal to 1), and includes monocyclic aromatic rings and fused aromatic rings formed by the fusion of two or more monocyclic aromatic rings. Unless otherwise specified, monocyclic aromatic rings are preferred as aromatic rings. Aromatic rings can be aromatic carbocyclic rings having only carbon atoms as ring constituent atoms, or aromatic heterocyclic rings having heteroatoms such as oxygen atoms, nitrogen atoms, and sulfur atoms in addition to carbon atoms as ring constituent atoms. 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, and even more preferably 6 or more, with an upper limit of preferably 24 or less, more preferably 18 or less or 14 or less, and even more preferably 10 or less.

[0013] In this specification, the term "aromatic group" refers to a group obtained by removing one or more hydrogen atoms from the aromatic ring of an aromatic compound. More specifically, a monovalent aromatic group refers to a group obtained by removing one hydrogen atom from the aromatic ring of an aromatic compound, and a divalent aromatic group refers to a group obtained by removing two hydrogen atoms from the aromatic ring of an aromatic compound. Examples of monovalent aromatic groups include optionally substituted aryl groups and optionally substituted heteroaryl groups, while examples of divalent aromatic groups include optionally substituted arylene groups and optionally substituted heteroarylene groups.

[0014] In this specification, the term "aliphatic group" refers to a group from which one or more hydrogen atoms bonded to an aliphatic carbon of an aliphatic compound have been removed. More specifically, a monovalent aliphatic group refers to a group from which one hydrogen atom bonded to an aliphatic carbon of an aliphatic compound has been removed, and a divalent aliphatic group refers to a group from which two hydrogen atoms bonded to an aliphatic carbon of an aliphatic compound have been removed. Examples of monovalent aliphatic groups include optionally substituted alkyl groups, optionally substituted cycloalkyl groups, optionally substituted alkenyl groups, and optionally substituted cycloalkenyl groups. Examples of divalent aliphatic groups include optionally substituted alkylene groups, optionally substituted cycloalkylene groups, optionally substituted alkenylene groups, and optionally substituted cycloalkenylene groups. In this specification, unless otherwise specified, the number of carbon atoms in the aliphatic group is preferably 1 or more, more preferably 2 or more, even more preferably 3 or more, 4 or more, 5 or more or 6 or more, preferably 50 or less, more preferably 40 or less, even more preferably 30 or less, 20 or less, 18 or less, 16 or less, 14 or less or 12 or less.

[0015] In this specification, the term "(meth)acryloyl group" includes acryloyl groups, methacryloyl groups, and combinations thereof. The term "(meth)acrylate compound" refers to a compound having a (meth)acryloyl group and includes acrylate compounds, methacrylate compounds, and combinations thereof. However, (meth)acrylic acid is not included in (meth)acrylate compounds. The term "(meth)acrylic acid" includes acrylic acid, methacrylic acid, and combinations thereof.

[0016] [Resin composition] The present invention provides a resin composition comprising (A) a compound containing one or more 2,2,6,6-tetramethylpiperidine-1-oxyl structures in its molecule, (B) an inorganic filler, (C) a maleimide resin, and (D) a vinyl resin having a specific structure, wherein component (D) is a resin selected from the group consisting of components (D-1), (D-2), and (D-3). The resin composition of the present invention may contain any additional components in combination with components (A) to (D). Examples of optional components include (E) curing accelerators, (F) thermosetting monomers, (G) organic fillers, (H) thermoplastic resins, (I) other additives, and (J) organic solvents. Hereinafter, a resin composition containing component (D-1) as component (D) will be referred to as the [resin composition according to the first embodiment], a resin composition containing component (D-2) will be referred to as the [resin composition according to the second embodiment], and a resin composition containing component (D-3) will be referred to as the [resin composition according to the third embodiment].

[0017] [Resin composition according to the first embodiment] The resin composition according to the first embodiment of the present invention includes (A) a compound containing one or more 2,2,6,6-tetramethylpiperidine-1-oxyl structures in its molecule, (B) an inorganic filler, (C) a maleimide resin, and (D-1) a vinyl resin containing a specific structural unit represented by formula (D1-1) and a specific end group, thereby providing a resin composition in which the dielectric loss tangent is reduced, crack resistance in desmear treatment is good, and plating penetration is suppressed. The following describes in detail each component contained in the resin composition according to the first embodiment.

[0018] <(A) Compounds containing one or more 2,2,6,6-tetramethylpiperidine-1-oxyl structures in the molecule> (A) Compounds containing one or more 2,2,6,6-tetramethylpiperidine-1-oxyl structures in their molecule (hereinafter referred to as TEMPO compounds) are usually free radicals, such as the 2,2,6,6-tetramethyl-1-piperidinyloxy free radical and radicals in which substituents are attached to its ring (piperidine ring). Radicals containing two or more 2,2,6,6-tetramethyl-1-piperidinyloxy structures linked by appropriate divalent or higher linking groups are also included in TEMPO compounds. TEMPO compounds may be used individually or in combination of two or more types. In the resin composition according to the first embodiment of the present invention, it is preferable to use a TEMPO-based compound that has a high boiling point and low volatility among TEMPO-based compounds. Examples of such TEMPO-based compounds include the group of compounds represented by the following formulas (A1) to (A7). [ka] [ka]

[0019] TEMPO compounds may be commercially available products, and examples of such commercially available products include "4-AcTEMPO" (compound represented by formula (A1)), "4-benzyloxyTEMPO" (compound represented by formula (A2)), "G-TEMPO" (compound represented by formula (A3)), "EGG-TEMPO(1)" (compound represented by formula (A4)), "EGG-TEMPO(2)" (compound represented by formula (A5)) [EGG-TEMPO is a mixture of EGG-TEMPO(1) and EGG-TEMPO(2)], "Sebacate TEMPO" (compound represented by formula (A6)), and "4-MCTEMPO" (compound represented by formula (A7)), all manufactured by Seiko Kogyo Co., Ltd.

[0020] In the resin composition according to the first embodiment, the content of component (A) in the resin composition is preferably 0.01% by mass or more, more preferably 0.015% by mass or more, even more preferably 0.02% by mass or more, 0.03% by mass or more, 0.04% by mass or more, and 0.05% by mass or more, with respect to 100% by mass of the nonvolatile component in the resin composition, preferably 0.5% by mass or less, more preferably 0.45% by mass or less, even more preferably 0.4% by mass or less, 0.3% by mass or less, and 0.2% by mass or less.

[0021] <(B) Inorganic filler> The resin composition according to this embodiment includes an inorganic filler as component (B). The inorganic filler (B) is in the form of particles of an inorganic material. The inorganic filler (B) is included in the resin composition in the form of particles and is usually included in the cured product while maintaining that particle state.

[0022] (B) Examples of inorganic fillers include silica, alumina, glass, cordierite, silicon oxide, barium sulfate, barium carbonate, talc, clay, mica powder, zinc oxide, hydrotalcite, boehmite, aluminum hydroxide, magnesium hydroxide, calcium carbonate, magnesium carbonate, magnesium oxide, boron nitride, aluminum nitride, manganese nitride, aluminum borate, strontium carbonate, strontium titanate, calcium titanate, magnesium titanate, bismuth titanate, titanium oxide, zirconium oxide, barium titanate, barium zirconate titanate, barium zirconate, calcium zirconate, zirconium phosphate, and zirconium tungstate phosphate. Among these, silica and alumina are preferred, and silica is particularly preferred. Therefore, (B) the inorganic filler preferably contains silica, and may contain only silica. Examples of silica include amorphous silica, fused silica, crystalline silica, synthetic silica, and hollow silica. Spherical silica is preferred as the silica. (B) The inorganic filler may be used alone or in combination of two or more types.

[0023] (B) Examples of commercially available inorganic fillers include "SP60-05" and "SP507-05" from Nippon Steel Chemical & Material Co., Ltd.; "YC100C", "YA050C", "YA050C-MJE", "YA010C", "SC2500SQ", "SO-C4", "SO-C2", and "SO-C1" from Admatex Co., Ltd.; "UFP-30", "DAW-03", and "FB-105FD" from Denka Co., Ltd.; "Silfil NSS-3N", "Silfil NSS-4N", and "Silfil NSS-5N" from Tokuyama Corporation; "Cellspheres" and "MGH-005" from Taiheiyo Cement Corporation; and "LHP-208" from Ube Eximo Co., Ltd.

[0024] (B) The average particle size of the inorganic filler is preferably 0.01 μm or more, more preferably 0.05 μm or more, even more preferably 0.1 μm or more, preferably 10 μm or less, more preferably 5 μm or less, even more preferably 3 μm or less, 1 μm or less, 0.8 μm or less, 0.6 μm or less, or 0.5 μm or less.

[0025] (B) The average particle size of the inorganic filler can be measured by the laser diffraction-scattering method based on Mie scattering theory. Specifically, the particle size distribution of the inorganic filler can be created on a volume basis using a laser diffraction-scattering particle size distribution analyzer, and the median diameter can be used as the average particle size. A sample can be prepared by weighing 100 mg of inorganic filler and 10 g of methyl ethyl ketone into a vial and dispersing them with ultrasound for 10 minutes. The sample can be measured using a laser diffraction-type particle size distribution analyzer with blue and red light source wavelengths, using a flow cell method to measure the volume-based particle size distribution of the inorganic filler, and the average particle size can be calculated as the median diameter from the obtained particle size distribution. An example of a laser diffraction-type particle size distribution analyzer is the "LA-960" manufactured by Horiba, Ltd.

[0026] (B) The specific surface area of ​​the inorganic filler is preferably 0.1 m². 2 / g or more, more preferably 0.5m 2 / g or more, more preferably 1m 2 / g or more, particularly preferably 3m 2 It is 1 / g or more, preferably 200m 2 Less than / g, more preferably 150m 2 / g or less, more preferably 100m 2 / g or less, 70m 2 / g or less, 50m 2 / g or less, particularly preferably 40m 2 (B) The specific surface area of ​​the inorganic filler can be measured by adsorbing nitrogen gas onto the sample surface using a specific surface area measuring device (Macsorb HM-1210, manufactured by Mountec Co., Ltd.) according to the BET method, and calculating the specific surface area using the BET multipoint method.

[0027] (B) The inorganic filler is preferably treated with a surface treatment agent from the viewpoint of improving moisture resistance and dispersibility. Examples of surface treatment agents include fluorine-containing silane coupling agents, aminosilane coupling agents, epoxysilane coupling agents, mercaptosilane coupling agents, silane coupling agents, alkoxysilanes, organosilazane compounds, titanate coupling agents, etc. One type of surface treatment agent may be used alone, or two or more types may be used in any combination.

[0028] Examples of commercially available surface treatment agents include "KBM403" (3-glycidoxypropyltrimethoxysilane), "KBM803" (3-mercaptopropyltrimethoxysilane), "KBE903" (3-aminopropyltriethoxysilane), "KBM573" (N-phenyl-3-aminopropyltrimethoxysilane), "SZ-31" (hexamethyldisilazane), "KBM103" (phenyltrimethoxysilane), "KBM-4803" (long-chain epoxy-type silane coupling agent), and "KBM-7103" (3,3,3-trifluoropropyltrimethoxysilane), all manufactured by Shin-Etsu Chemical Co., Ltd.

[0029] From the viewpoint of improving the dispersibility of the inorganic filler, the degree of surface treatment by the surface treatment agent is preferably within a specific range. Specifically, 100% by mass of the inorganic filler is preferably surface-treated with 0.2% to 5% by mass of the surface treatment agent, more preferably with 0.2% to 3% by mass of the surface treatment agent, and even more preferably with 0.3% to 2% by mass of the surface treatment agent.

[0030] The degree of surface treatment by a surface treatment agent can be evaluated by the amount of carbon per unit surface area of ​​the inorganic filler. From the viewpoint of improving the dispersibility of the inorganic filler, the amount of carbon per unit surface area of ​​the inorganic filler should be 0.02 mg / m². 2 The above is preferred, and 0.1 mg / m²2 The above is more preferable, 0.2 mg / m² 2 The above is even more preferable. On the other hand, from the viewpoint of preventing an increase in the melt viscosity of the resin composition layer, 1.0 mg / m 2 The following is preferred: 0.8 mg / m² 2 The following is more preferable: 0.5 mg / m² 2 The following are even more preferable.

[0031] (B) The amount of carbon per unit surface area of ​​the inorganic filler can be measured after cleaning the inorganic filler with a solvent (e.g., methyl ethyl ketone (MEK)) following surface treatment. Specifically, a sufficient amount of MEK as the solvent is added to the inorganic filler that has been surface-treated with a surface treatment agent, and ultrasonic cleaning is performed at 25°C for 5 minutes. After removing the supernatant and drying the solids, the amount of carbon per unit surface area of ​​the inorganic filler can be measured using a carbon analyzer. As a carbon analyzer, a Horiba "EMIA-320V" or similar can be used.

[0032] In the resin composition according to the first embodiment, the content of component (B) in the resin composition is preferably 50% by mass or more, more preferably 55% by mass or more, even more preferably 60% by mass or more, preferably 85% by mass or less, more preferably 80% by mass or less, and even more preferably 75% by mass or less, based on 100% by mass of the nonvolatile components in the resin composition, from the viewpoint of reducing the dielectric loss tangent.

[0033] (C) Maleimide resin The resin composition according to the first embodiment of the present invention contains (C) maleimide resin as component (C). The (C) maleimide resin may be used alone or in combination of two or more types.

[0034] (C) The maleimide resin may be an aromatic maleimide resin having a maleimide group directly bonded to the aromatic ring, or it may be an aliphatic maleimide resin not having a maleimide group directly bonded to the aromatic ring. (C) If the maleimide resin includes an aliphatic maleimide resin, it is preferable that the aliphatic maleimide resin includes a maleimide resin having a carbon skeleton derived from dimer acid. (C) If the maleimide resin includes an aromatic maleimide resin, it is preferable that the aromatic maleimide resin includes a maleimide resin having one or more skeletons selected from a biphenyl skeleton, an indane skeleton, and an aralkyl skeleton.

[0035] The carbon skeleton derived from dimer acid refers to a carbon skeleton obtained by removing the two terminal carboxyl groups (-COOH) of dimer acid, or a carbon skeleton obtained by replacing the two terminal carboxyl groups (-COOH) with methylene groups (-CH2-). Dimer acid is a known compound obtained by dimerizing unsaturated fatty acids (preferably those with 11 to 22 carbon atoms, more preferably those with 14 to 20 carbon atoms, and particularly preferably those with 18 carbon atoms), and its industrial production process is largely standardized in the industry. Dimer acid is readily available, especially those mainly composed of 36-carbon dimer acid obtained by dimerizing 18-carbon unsaturated fatty acids such as oleic acid and linoleic acid, which are inexpensive and readily available. In addition, dimer acid may contain arbitrary amounts of monomeric acids, trimeric acids, and other polymerized fatty acids depending on the production method, degree of purification, etc. Furthermore, although double bonds remain after the polymerization reaction of unsaturated fatty acids, in this specification, hydrogenated products obtained by further hydrogenation to reduce the degree of unsaturation are also included as dimer acid.

[0036] Maleimide resins having a carbon skeleton derived from dimer acid include maleimide resins represented by formula (C1).

[0037] [ka]

[0038] (In formula (C1), Each of the q1+1 W groups independently represents a divalent organic group consisting of five or more skeletal atoms selected from carbon atoms, nitrogen atoms (that do not form imides), oxygen atoms, and sulfur atoms, and non-skeletal atoms selected from hydrogen atoms and halogen atoms; and at least one of the q1+1 W groups represents a divalent hydrocarbon group derived from a dimer acid; Each Z independently represents a tetravalent organic group consisting of five or more skeletal atoms selected from carbon atoms, nitrogen atoms (that do not form imides), oxygen atoms, and sulfur atoms, and non-skeletal atoms selected from hydrogen atoms and halogen atoms; q1 represents 0 or an integer greater than or equal to 1.

[0039] In formula (C1), each of the q1+1 Ws independently represents a divalent organic group consisting of five or more (preferably 5 to 200, more preferably 5 to 100, and even more preferably 5 to 50) skeletal atoms selected from carbon atoms, nitrogen atoms (that do not form imides), oxygen atoms, and sulfur atoms, and non-skeletal atoms selected from hydrogen atoms and halogen atoms. At least one of the q1+1 Ws represents a divalent hydrocarbon group derived from a dimer acid.

[0040] A divalent hydrocarbon group derived from dimer acid refers to a divalent hydrocarbon group obtained by removing the two terminal carboxyl groups (-COOH) of a dimer acid, or a divalent hydrocarbon group obtained by replacing the two terminal carboxyl groups (-COOH) with methylene groups (-CH2-).

[0041] The q1+1 W atoms may have divalent organic groups other than divalent hydrocarbon groups derived from dimer acid, but when the q1+1 X atoms are considered to be 100 mol%, it is preferable that 30 mol% or more of them are divalent hydrocarbon groups derived from dimer acid, more preferably that 60 mol% or more are divalent hydrocarbon groups derived from dimer acid, even more preferably that 90 mol% or more are divalent hydrocarbon groups derived from dimer acid, and even more preferably that all of the q1+1 W atoms are divalent hydrocarbon groups derived from dimer acid.

[0042] The divalent organic groups in q1+1 W, other than the divalent hydrocarbon groups derived from the dimer acid, may be divalent organic groups without an aromatic ring, or they may be divalent organic groups having an aromatic ring.

[0043] In formula (C1), each of the q1 Z independently represents a tetravalent organic group consisting of five or more (preferably 5 to 200, more preferably 5 to 100, and even more preferably 5 to 50) skeletal atoms selected from carbon atoms, nitrogen atoms (that do not form imides), oxygen atoms, and sulfur atoms, and non-skeletal atoms selected from hydrogen atoms and halogen atoms. The tetravalent organic group represented by Z may be a tetravalent organic group without an aromatic ring, or a tetravalent organic group having an aromatic ring.

[0044] In one embodiment, the tetravalent organic group represented by Z is preferably a tetravalent group selected from the following formulas (Z1) to (Z5).

[0045] [ka]

[0046] (In formulas (Z1) to (Z5), Ring Z 11 , ring Z 21 , ring Z 22 , ring Z 31 , ring Z 32 , ring Z 33 , ring Z 41 , ring Z 42 , ring Z 43 , ring Z 44 , ring Z 51 , ring Z 52 , ring Z 53 , ring Z 54 and ring Z 55 Each of these independently represents an aromatic ring which may have substituents, or an unaromatic ring which may have substituents; Z 2a , Z 3a , Z 3b , Z 4a , Z 4b , Z 4c , Z 5a , Z5b , Z 5c and Z 5d each independently represent a single bond, -C(R C1 )2-, -O-, -CO-, -S-, -SO-, -SO2-, -CONH-, or -NHCO-; R C1 each independently represent a hydrogen atom or an alkyl group which may be substituted with a halogen atom, or two R bonded to the same carbon atom C1 are bonded together to form a non-aromatic ring which may have a substituent; the wavy line represents a bonding site; the two bonding sites on the same ring represented by the wavy lines are respectively bonding sites to two adjacent carbon atoms on the ring.)

[0047] In formulas (Z1) to (Z5), ring Z 11 , ring Z 21 , ring Z 22 , ring Z 31 , ring Z 32 , ring Z 33 , ring Z 41 , ring Z 42 , ring Z 43 , ring Z 44 , ring Z 51 , ring Z 52 , ring Z 53 , ring Z 54 and ring Z 55 each independently represent an aromatic ring which may have a substituent, or a non-aromatic ring which may have a substituent. These cyclic structures are preferably an aromatic ring which may have a substituent, more preferably a benzene ring which may have a substituent, and even more preferably a benzene ring which may be substituted with an alkyl group.

[0048] The non-aromatic ring means a ring other than an aromatic ring having aromaticity over the entire ring. The non-aromatic ring may be a non-aromatic carbocyclic ring having only carbon atoms as ring-constituting atoms, or may be a non-aromatic heterocyclic ring having, as ring-constituting atoms, a heteroatom such as an oxygen atom, a nitrogen atom, or a sulfur atom in addition to carbon atoms. The non-aromatic ring is preferably a non-aromatic carbocyclic ring. The non-aromatic ring may be a saturated ring or an unsaturated ring. The non-aromatic ring is preferably a 3 to 21-membered non-aromatic ring, more preferably a 4 to 17-membered non-aromatic ring, and even more preferably a 5 to 14-membered non-aromatic ring. Preferable specific examples of the non-aromatic ring (non-aromatic carbocyclic ring) include monocyclic non-aromatic saturated carbocyclic rings such as a cyclobutane ring, a cyclopentane ring, a cyclohexane ring, a cycloheptane ring, and a cyclooctane ring; monocyclic non-aromatic unsaturated carbocyclic rings such as a cyclobutene ring, a cyclopentene ring, a cyclohexene ring, a cycloheptene ring, a cyclooctene ring, a cyclopentadiene ring, and a cyclohexadiene ring; a bicyclo[2.2.1]heptane ring (norbornane ring), a bicyclo[4.4.0]decane ring (decalin ring), a bicyclo[5.3.0]decane ring, a bicyclo[4.3.0]nonane ring (hydrindane ring), a bicyclo[3.2.1]octane ring, a bicyclo[5.4.0]undecane ring, a bicyclo[3.3.0]octane ring, a bicyclo[3.3.1]nonane ring, a tricyclo[5.2.1.0 2,6 decane ring (tetrahydrodicyclopentadiene ring), a tricyclo[3.3.1.1 3,7 decane ring (adamantane ring), a tricyclo[6.2.1.0 2,7 undecane ring and other bicyclic or higher non-aromatic saturated carbocyclic rings; and bicyclic or higher non-aromatic unsaturated carbocyclic rings such as a bicyclo[2.2.1]hept-2-ene ring (norbornene ring), a bicyclo[2.2.2]oct-2-ene ring, and a bicyclo[4.4.0]dec-2-ene ring. The non-aromatic ring may be a non-aromatic ring partially condensed with an aromatic ring. Examples of the non-aromatic ring partially condensed with an aromatic ring include an indane ring, an indene ring, a tetralin ring, a 1,2-dihydronaphthalene ring, a 1,4-dihydronaphthalene ring, a fluorene ring, a 9,10-dihydroanthracene ring, and a 9,10-dihydrophenanthrene ring.

[0049] ring Z 11 , ring Z21 , ring Z 22 , ring Z 31 , ring Z 32 , ring Z 33 , ring Z 41 , ring Z 42 , ring Z 43 , ring Z 44 , ring Z 51 , ring Z 52 , ring Z 53 , ring Z 54 and ring Z 55 The substituents that can be present are not particularly limited, but include, for example, halogen atoms, -NO2, -CN, -COH, -OH, -SH, -NH2, -COOH, -R C , -COR C , -OR C , -SR C -SOR C , -SO2R C , -NHR C , -NR C ,-COOR C , -OCOR C -CONH2, -CONHR C ,-CONR C , -NHCOR C Examples of monovalent substituents include (where R C Each of these independently represents a monovalent hydrocarbon group.

[0050] R C The number of carbon atoms in the monovalent hydrocarbon group shown is preferably 1 to 50, more preferably 1 to 20. C The monovalent hydrocarbon group indicated by may be a monovalent saturated hydrocarbon group or a monovalent unsaturated hydrocarbon group. Also, R C The monovalent hydrocarbon group indicated by may or may not have an aromatic structure. C Examples of monovalent hydrocarbon groups represented by include alkyl groups, alkenyl groups, aryl groups, aralkyl groups, and alkylaryl groups.

[0051] Alkyl groups may be linear, branched, or cyclic. The number of carbon atoms in an alkyl group is preferably 1 to 14, more preferably 1 to 10, even more preferably 1 to 6, and particularly preferably 1 to 3. Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, sec-pentyl, neopentyl, tert-pentyl, hexyl, isohexyl, heptyl, isoheptyl, octyl, isooctyl, tert-octyl, cyclopentyl, cyclohexylmethyl, and the like.

[0052] The alkenyl group may be linear, branched, or cyclic. The number of carbon atoms in the alkenyl group is preferably 2 to 14, more preferably 2 to 10, even more preferably 2 to 6, and particularly preferably 2 to 3. Examples of alkenyl groups include vinyl group, propenyl group (allyl group, 1-propenyl group, isopropenyl group), butenyl group (1-butenyl group, clotyl group, methallyl group, isoclotyl group, etc.), pentenyl group (1-pentenyl group, etc.), hexenyl group (1-hexenyl group, etc.), heptenyl group (1-heptenyl group, etc.), octenyl group (1-octenyl group, etc.), cyclopentenyl group (2-cyclopentenyl group, etc.), cyclohexenyl group (3-cyclohexenyl group), and the like.

[0053] The number of carbon atoms in the aryl group is preferably 6 to 14, more preferably 6 to 10. Examples of aryl groups include phenyl, 1-naphthyl, and 2-naphthyl groups.

[0054] The aralkyl group may be an alkyl group substituted with one or more (preferably one) aryl groups. The number of carbon atoms in the aralkyl group is preferably 7 to 15, more preferably 7 to 11. Examples of aralkyl groups include benzyl group, phenethyl group, hydrocinnamyl group, α-methylbenzyl group, α-cumyl group, 1-naphthylmethyl group, and 2-naphthylmethyl group.

[0055] The alkylaryl group may be an aryl group substituted with one or more (preferably one) alkyl groups. The number of carbon atoms in the alkylaryl group is preferably 7 to 15, more preferably 7 to 11. Examples of alkylaryl groups include 4-methylphenyl, 3-methylphenyl, 2-methylphenyl, 4-ethylphenyl, 3-ethylphenyl, 2-ethylphenyl, 4-isopropylphenyl, 3-isopropylphenyl, and 2-isopropylphenyl.

[0056] In equations (Z1) to (Z5), Z 2a , Z 3a , Z 3b , Z 4a , Z 4b , Z 4c , Z 5a , Z 5b , Z 5c and Z 5d These are, independently, single bonds, -C(R C1 )2-, -O-, -CO-, -S-, -SO-, -SO2-, -CONH-, or -NHCO-, preferably a single bond, -C(R C1 It is 2- or -O-.

[0057] R C1 Each of these independently represents an alkyl group which may be substituted with a hydrogen atom or a halogen atom, or two R atoms bonded to the same carbon atom. C1 They bond together to form a non-aromatic ring which may have substituents. The alkyl group is R C It may be the same as the alkyl group in R. C1 Each of these independently preferably represents an alkyl group which may be substituted with a hydrogen atom or a halogen atom; more preferably represents a methyl group which may be substituted with a hydrogen atom or a halogen atom; even more preferably represents a hydrogen atom, a methyl group or a trifluoromethyl group; and even more preferably represents a hydrogen atom or a methyl group.

[0058] R C1The substituents that can be present are not particularly limited, but include, for example, halogen atoms, -NO2, -CN, -COH, -OH, -SH, -NH2, -COOH, -R C , -COR C , -OR C , -SR C -SOR C , -SO2R C , -NHR C , -NR C ,-COOR C , -OCOR C -CONH2, -CONHR C ,-CONR C , -NHCOR C Examples of monovalent substituents include (R C (As stated above).

[0059] In formula (C1), q1 represents 0 or an integer greater than or equal to 1, preferably an integer between 0 and 10, and more preferably 0.

[0060] Examples of aromatic maleimide resins include maleimide resins represented by formula (C2).

[0061] [ka]

[0062] (In formula (C2), Ring C A21 and ring C A22 Each of these independently represents an aromatic carbon ring which may have substituents; R A21 Each of these independently represents an alkyl group which may be substituted with a hydrogen atom or a halogen atom; q A21 Each of these independently represents a non-negative integer; q A22 represents an integer greater than or equal to 1; q A21 Units and q A22 The units may be the same or different for each unit.

[0063] In equation (C2), ring C A21 and ring C A22 Each of these independently represents an aromatic carbon ring which may have substituents. Here, ring C A21 A maleimide group bonded to it, and -C(R A21 For the group represented by )2-, the ring C A21 It is not included in the substituents that it may have. Similarly, ring C A22 -C(R A21 For the group represented by )2-, ring C A22 The substituents that it may have are not included. Aromatic carbon rings are ring Z 11 , ring Z 21 , ring Z 22 , ring Z 31 , ring Z 32 , ring Z 33 , ring Z 41 , ring Z 42 , ring Z 43 , ring Z 44 , ring Z 51 , ring Z 52 , ring Z 53 , ring Z 54 and ring Z 55 It may be the same as the aromatic carbocyclic ring described in the section on aromatic rings. Also, C A21 and ring C A22 In this context, "substituent" refers to, for example, ring Z. 11 , ring Z 21 , ring Z 22 , ring Z 31 , ring Z 32 , ring Z 33 , ring Z 41 , ring Z 42 , ring Z 43 , ring Z 44 , ring Z 51 , ring Z 52 , ring Z 53 , ring Z 54 and ring Z 55 The substituents may be the same as those that can be present in ring C. A21 and ring C A22Each of these independently preferably represents a benzene ring which may have substituents; more preferably represents a benzene ring which may be substituted with a group selected from alkyl and aryl groups; and even more preferably represents an (unsubstituted) benzene ring.

[0064] In equation (C2), R A21 Each of these independently represents an alkyl group which may be substituted with a hydrogen atom or a halogen atom. The alkyl group is R C It may be the same as the alkyl group in R. A21 Each of these independently preferably represents a hydrogen atom or an alkyl group; more preferably a hydrogen atom or a methyl group; among them, q A21 In the embodiment where R is 0, A21 It is even more preferable that it be a hydrogen atom. Also, q A21 In the configuration where is an integer greater than or equal to 1, R A21 It is even more preferable that it be a methyl group.

[0065] In equation (C2), q A21 Each of these independently represents an integer greater than or equal to 0, preferably an integer between 0 and 10, more preferably an integer between 0 and 5, even more preferably 0, 1, or 2, and even more preferably 0 or 1. In an aromatic maleimide compound represented by formula (C2), there are multiple q A21 They may be the same or different, but it is preferable that they be the same. Also, q A22 This represents an integer greater than or equal to 1, preferably an integer between 1 and 10.

[0066] Another example of an aromatic maleimide resin is the maleimide resin represented by the following formula (C3).

[0067] [ka]

[0068] (In formula (C3), R C3Each of these independently represents an alkyl group which may be substituted with a hydrogen atom or a halogen atom; Ring C 31 , ring C 32 and ring C 33 Each of these independently represents an aromatic carbon ring which may have substituents; q3 represents an integer greater than or equal to 1; q3 The units may be the same or different for each unit.

[0069] In equation (C3), R C3 Each of these independently represents an alkyl group which may be substituted with a hydrogen atom or a halogen atom. The alkyl group is R C It may be the same as the alkyl group in R. C3 Each of these is preferably a hydrogen atom or an alkyl group, more preferably a hydrogen atom or a methyl group, and even more preferably a hydrogen atom.

[0070] In equation (C3), ring C 31 , ring C 32 and ring C 33 Each of these independently represents an aromatic carbon ring which may have substituents. 31 , ring C 32 and ring C 33 The aromatic carbon ring shown is ring Z. 11 , ring Z 21 , ring Z 22 , ring Z 31 , ring Z 32 , ring Z 33 , ring Z 41 , ring Z 42 , ring Z 43 , ring Z 44 , ring Z 51 , ring Z 52 , ring Z 53 , ring Z 54 and ring Z 55 It may be the same as the aromatic carbon ring described in the section on aromatic rings. Also, ring C 31 , ring C 32 and ring C 33 In this context, "substituent" refers to, for example, ring Z. 11 , ring Z 21, ring Z 22 , ring Z 31 , ring Z 32 , ring Z 33 , ring Z 41 , ring Z 42 , ring Z 43 , ring Z 44 , ring Z 51 , ring Z 52 , ring Z 53 , ring Z 54 and ring Z 55 The substituents may be the same as those that can be present in ring C. 31 , ring C 32 and ring C 33 Each of these is preferably an optionally substituted benzene ring, more preferably an optionally substituted benzene ring with a group selected from alkyl and aryl groups, and even more preferably an unsubstituted benzene ring.

[0071] In formula (C3), q3 represents an integer greater than or equal to 1, and is preferably an integer between 1 and 10.

[0072] Another example of an aromatic maleimide resin is the maleimide resin represented by the following formula (C4).

[0073] [ka]

[0074] (In formula (C4), R C4 Each of these independently represents an alkyl group; Ring C 41 and ring C 42 Each of these independently represents an aromatic carbon ring which may have substituents; q4 represents an integer greater than or equal to 1; q4 The units may be the same or different for each unit.

[0075] In equation (C4), R C4 Each of these independently represents an alkyl group. C4It is preferable that it be a methyl group.

[0076] In equation (C4), ring C 41 Each of these independently represents an aromatic ring which may have substituents. Also, ring C 41 In this context, "substituent" refers to, for example, ring Z. 11 , ring Z 21 , ring Z 22 , ring Z 31 , ring Z 32 , ring Z 33 , ring Z 41 , ring Z 42 , ring Z 43 , ring Z 44 , ring Z 51 , ring Z 52 , ring Z 53 , ring Z 54 and ring Z 55 The substituents may be the same as those that can be present in ring C. 41 Each of these is preferably an optionally substituted benzene ring, more preferably an optionally substituted benzene ring with an alkyl group, and even more preferably an alkyl group-substituted benzene ring.

[0077] In equation (C4), ring C 42 Each of these independently represents an aromatic ring which may have substituents. Also, ring C 42 In this context, "substituent" refers to, for example, ring Z. 11 , ring Z 21 , ring Z 22 , ring Z 31 , ring Z 32 , ring Z 33 , ring Z 41 , ring Z 42 , ring Z 43 , ring Z 44 , ring Z 51 , ring Z 52 , ring Z 53 , ring Z 54 and ring Z 55 The substituents may be the same as those that can be present in ring C. 42Each of these is preferably an optionally substituted benzene ring, more preferably an optionally substituted alkyl group benzene ring, and even more preferably an unsubstituted benzene ring.

[0078] In equation (C4), q4 represents an integer greater than or equal to 1, and is preferably an integer between 1 and 20.

[0079] Another example of an aromatic maleimide resin is the maleimide resin represented by the following formula (C5-1).

[0080] [ka]

[0081] (In formula (C5-1), R C51 Each of these independently represents an alkylene group; R C52 represents a hydrogen atom or a monovalent hydrocarbon group which may have substituents; R C53 represents a hydrogen atom or a group represented by the following formula (C5-2); Ring C 51 and ring B 52 Each of these independently represents an aromatic carbon ring which may have substituents; q 51 represents an integer greater than or equal to 1; q 52 Each of these independently represents an integer greater than or equal to 1; q 51 The units may be the same or different for each unit; q 52 The units may be the same or different for each unit.

[0082] [ka]

[0083] (In formula (C5-2), The wavy line indicates a connection point; The other symbols are as described above.

[0084] In equation (C5-1), R C51 Each of these independently represents an alkylene group. C51 It is preferable that the group is a methylene group, an ethylene group, or an ethylidene group.

[0085] In equation (C5-1), R C52 Each of these independently represents a hydrogen atom or a monovalent hydrocarbon group which may have substituents. C52 Examples of monovalent hydrocarbon groups include monovalent aliphatic groups, monovalent aromatic groups, or monovalent groups consisting of combinations thereof.

[0086] In equations (C5-1) and (C5-2), ring C 51 Each of these independently represents an aromatic carbon ring which may have substituents. 51 In this context, "substituent" refers to, for example, ring Z. 11 , ring Z 21 , ring Z 22 , ring Z 31 , ring Z 32 , ring Z 33 , ring Z 41 , ring Z 42 , ring Z 43 , ring Z 44 , ring Z 51 , ring Z 52 , ring Z 53 , ring Z 54 and ring Z 55 The substituents may be the same as those that can be present in ring B. 51 Each of these is preferably an optionally substituted benzene ring, more preferably an optionally substituted benzene ring with an alkyl group, even more preferably an alkyl group-substituted benzene ring, even more preferably a benzene ring with an alkyl group substituted at one ortho position relative to the maleimide group, and still more preferably a benzene ring with an ethyl group substituted at one ortho position relative to the maleimide group.

[0087] In equation (C5-1), ring C 52 This represents an aromatic carbon ring which may have substituents. 52 In this context, "substituent" refers to, for example, ring Z. 11 , ring Z 21 , ring Z 22 , ring Z 31 , ring Z 32 , ring Z 33 , ring Z 41 , ring Z 42 , ring Z 43 , ring Z 44 , ring Z 51 , ring Z 52 , ring Z 53 , ring Z 54 and ring Z 55 The substituents may be the same as those that can be present in ring C. 52 It is preferably a benzene ring which may have substituents, and more preferably a benzene ring which may be substituted with an alkyl group.

[0088] In equation (C5-1), q 51 represents an integer greater than or equal to 1. Also, q 52 Each of these independently represents an integer of 1 or more, preferably an integer between 1 and 50, preferably an integer between 1 and 30, and more preferably an integer between 1 and 15.

[0089] The maleimide group equivalent of (C) maleimide resin is preferably 50 g / eq. or more, more preferably 100 g / eq. or more, even more preferably 150 g / eq. or more, 200 g / eq. or more, 250 g / eq. or more, or 300 g / eq. or more, with an upper limit preferably 2,000 g / eq. or less, more preferably 1,000 g / eq. or less, even more preferably 800 g / eq. or less, 600 g / eq. or less, 500 g / eq. or less, or 450 g / eq. or less. The maleimide group equivalent is the mass of (C) maleimide resin per molar equivalent of maleimide groups.

[0090] (C) The molecular weight of the maleimide resin is preferably less than 5,000, more preferably less than 3,000, even more preferably less than 2,000, less than 1,500, less than 1,200, or less than 1,000, and the lower limit is not particularly limited, but may be, for example, 300 or more, 400 or more, 500 or more, etc.

[0091] Examples of commercially available maleimide resins include dimeramine structure-containing maleimide resins such as "SLK-2600" and "SLK-6895-T90" from Shin-Etsu Chemical Co., Ltd.; dimeramine structure-containing maleimide resins such as "BMI-1500," "BMI-1700," "BMI-3000J," "BMI-689," and "BMI-2500" from Designer Molecules Inc.; aromatic maleimide resins such as "BMI-6100" from Designer Molecules Inc.; biphenyl aralkyl type maleimide resins such as "MIR-5000-60T," "MIR-3000-70MT," and "MIR-3000-70T" from Nippon Kayaku Co., Ltd.; "BMI-70" and "BMI-80" from K.I. Chemicals Co., Ltd.; and "BMI-2300" and "BMI-TMH" from Yamato Chemical Industries, Ltd. Alternatively, a maleimide resin (indane ring skeleton-containing maleimide compound) disclosed in the Japan Institute of Invention and Innovation, Technical Report No. 2020-500211 may be used as the maleimide resin.

[0092] Furthermore, the maleimide resin represented by formula (C5-1) may be synthesized by known synthesis methods, for example, or a commercially available product may be used. Examples of known synthesis methods include the method described in Synthesis Example 1 of Japanese Patent Application Publication No. 2024-102755. As the maleimide resin represented by formula (C5-1), a maleimide resin produced by the following steps (1) and (2) may also be used. Step (1): A step in which an aromatic amine compound represented by the following formula (c1) is reacted with a compound having a benzyl ether skeleton under the influence of a solid acid catalyst. Step (2): A step of condensing the intermediate amine compound produced in step (1) with maleic anhydride.

[0093] [ka]

[0094] (In formula (c1), R c1 This represents a hydrocarbon group with 1 to 18 carbon atoms; R c2 and R c3 Each of these independently represents a hydrogen atom or a hydrocarbon group having 1 to 18 carbon atoms; R c4 and R c5 Each of these independently represents either a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.

[0095] The content of (C) maleimide resin in the resin composition is not particularly limited when the non-volatile components in the resin composition are considered to be 100% by mass, but from the viewpoint of improving adhesion strength with the conductive layer, it is preferably 0.1% by mass or more, more preferably 1% by mass or more, even more preferably 2% by mass or more, 5% by mass or more, 8% by mass or more, and even more preferably 2.5% by mass or more, with an upper limit of preferably 40% by mass or less, more preferably 30% by mass or less, and even more preferably 20% by mass or less.

[0096] <(D-1) Compounds containing a first specific structural unit and a specific terminal group> The resin composition according to the first embodiment of the present invention includes a compound containing a structural unit represented by the following formula (D1-1) and an end group represented by the following formula (y) as component (D-1) (a compound containing a first specific structural unit and a specific end group). Hereinafter, the structural unit represented by formula (D1-1) may be referred to as the "first specific structural unit" or "structural unit (1)". Component (D-1) may be used alone or in combination of two or more types.

[0097] [ka]

[0098] (In formula (D1-1), R 1 Each of these independently represents a divalent nitrogen-containing heteroaromatic group which may have substituents, R 2 Each of these independently represents a divalent organic group. X 1 These are, independently, -O-, -S-, or -N(R 3 )- represents, R 3 (This represents a hydrogen atom, a monovalent hydrocarbon group having 1 to 20 carbon atoms, a monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms, or a group in which the hydrocarbon group or a portion of the halogenated hydrocarbon group is substituted with at least one atom selected from oxygen and sulfur atoms.)

[0099] [ka]

[0100] (In formula (y), Y represents a monovalent organic group with 3 to 50 carbon atoms that contains a radical polymerizable group other than a maleimide group. The wavy line indicates a connection point.

[0101] In equation (D1-1), R 1 Each of these independently represents a divalent nitrogen-containing heteroaromatic group which may have substituents. A divalent nitrogen-containing heteroaromatic group is a group obtained by removing two hydrogen atoms from the nitrogen-containing heteroaromatic ring of a nitrogen-containing heteroaromatic compound. Examples of nitrogen-containing heteroaromatic rings include pyrrole rings, pyridine rings, pyrimidine rings, pyrazine rings, pyridazine rings, triazine rings, quinoline rings, isoquinoline rings, quinoxaline rings, phthalazine rings, quinazoline rings, naphthyridine rings, carbazole rings, acridine rings, and phenazine rings. 1 The group represented is preferably a divalent group consisting of a pyrimidine ring which may have substituents.

[0102] R 1There are no particular restrictions on the substituents that the group represented by can have, but examples include halogen atoms, monovalent hydrocarbon groups having 1 to 20 carbon atoms, monovalent halogenated hydrocarbon groups having 1 to 20 carbon atoms, groups in which the hydrocarbon group or a part of the halogenated hydrocarbon group is substituted with at least one atom selected from oxygen and sulfur atoms, nitro groups, cyano groups, amino groups, groups consisting of amine salts, etc.

[0103] Examples of halogen atoms used as substituents include fluorine, chlorine, bromine, and iodine atoms.

[0104] Examples of monovalent hydrocarbon groups having 1 to 20 carbon atoms as substituents include monovalent aliphatic groups, monovalent aromatic groups, or monovalent groups consisting of combinations thereof. The monovalent aliphatic group may be either a monovalent saturated aliphatic group or a monovalent unsaturated aliphatic group. The monovalent aliphatic group may be a linear hydrocarbon group, a cyclic hydrocarbon group (i.e., an alicyclic hydrocarbon group), or a combination thereof. Furthermore, the linear hydrocarbon group may be either linear or branched.

[0105] Examples of monovalent aliphatic groups include alkyl groups. Examples of alkyl groups include methyl group, ethyl group, n-propyl group, 2-propyl group, n-butyl group, isobutyl group, t-butyl group, n-pentyl group, 1-ethylpropyl group, 1-methylbutyl group, 2-methylbutyl group, 3-methylbutyl group, amyl group, cyclopentyl group, 2,2-dimethylpropyl group, 1,1-dimethylpropyl group, n-hexyl group, cyclohexyl group, 1-ethylbutyl group, 2-ethylbutyl group, 3-ethylbutyl group, 1-methylpentyl group, 2-methylpentyl group, 3-methylpentylene group, and 4-methylpentylene group. n-heptyl group, 1,1-dimethylbutylene group, 2,2-dimethylbutylene group, 3,3-dimethylbutyl group, 1,2-dimethylbutyl group, 1,3-dimethylbutyl group, 2,3-dimethylbutyl group, n-heptyl group, 1-methylhexyl group, 2-methylhexyl group, 3-methylhexyl group, 4-methylhexyl group, 5-methylhexyl group, 1-ethylpentyl group, 2-ethylpentyl group, 3-ethylpentyl group, 1,1-dimethylpentyl group, 2,2-dimethylpentyl group, 3,3-dimethylpentyl group, 4,4-dimethylpentyl group, 1,2-dimethylbutyl Lupentyl group, 1,3-dimethylpentyl group, 1,4-dimethylpentyl group, 2,3-dimethylpentyl group, 2,4-dimethylpentyl group, 3,4-dimethylpentyl group, 2-methyl-3,3-dimethylbutyl group, 1-methyl-3,3-dimethylbutyl group, 1,2,3-trimethylbutyl group, 1,3-dimethyl-2-pentyl group, 2-isopropylbutyl group, 2-methylcyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 1-cyclohexylmethyl group, 2-ethylcyclopentyl group, 3-ethylcyclopentyl n-octyl group, 2,3-dimethylcyclopentyl group, 2,4-dimethylcyclopentyl group, 2-methylcyclopentylmethyl group, 2-cyclopentylethyl group, 1-cyclopentylethyl group, n-octyl group, 2-octyl group, 3-octyl group, 4-octyl group, 2-methylheptyl group, 3-methylheptyl group, 4-methylheptyl group, 5-methylheptyl group, 6-methylheptyl group, 2-ethylhexyl group, 3-ethylhexyl group, 4-ethylhexyl group, 5-ethylhexyl group, 1,1-dimethylhexyl group, 2,2-dimethylhexyl group, 3,3-dimethylhexyl group, 4,4-dimethylhexyl group, 5,5-dimethylhexyl group, 1,2-dimethylhexyl group, 1,3-dimethylhexyl group, 1,4-dimethylhexyl group, 1,5-dimethylhexyl group, 2,3-dimethylhexyl group, 2,4-dimethylhexyl group, 2,5-dimethylhexyl group, 1,1-ethylmethylpentyl group, 2,2-ethylmethylpentyl group, 3,3-ethylmethylpentyl group, 4,4-ethylmethylpentyl group, 1-ethyl-2-methylpentyl 1-(2-methylpropyl)butyl group, Propyl)-2-methylbutyl group, 1,1-(2-methylpropyl)ethyl group, 1,1-(2-methylpropyl)ethylpropyl group, 1,1-diethylpropyl group, 2,2-diethylpropyl group, 1,1-ethylmethyl-2,2-dimethylpropyl group, 2,2-ethylmethyl-1,1-dimethylpropyl group, 2-ethyl-1,1-dimethylbutyl group, 2,3-dimethylcyclohexyl group, 2,3-dimethylcyclohexyl group, 2,5-dimethylcyclohexyl group, 2,6-dimethyl Examples include cyclohexyl group, 3,5-dimethylcyclohexyl group, 2-methylcyclohexylmethyl group, 3-methylcyclohexylmethyl group, 4-methylcyclohexylmethyl group, 2-ethylcyclohexyl group, 3-ethylcyclohexyl group, 4-ethylcyclohexyl group, 2-cyclohexylethyl group, 1-cyclohexylethyl group, 1-cyclohexyl-2-ethylene group, nonyl group, isononyl group, decyl group, isodecyl group, undecyl group, dodecyl group, propargyl group, etc.

[0106] Specific examples of monovalent aromatic groups include aryl groups. Examples of aryl groups include phenyl groups, naphthyl groups, anthracenyl groups, and biphenyl groups (-C6H4-C6H5).

[0107] Examples of "monovalent groups consisting of combinations of these" among monovalent hydrocarbon groups having 1 to 20 carbon atoms include the benzyl group and the 2-phenylethyl group.

[0108] A monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms as a substituent includes a group in which some or all of the hydrogen atoms of the "monovalent hydrocarbon group having 1 to 20 carbon atoms" as a substituent are replaced with halogen atoms. The halogen atoms constituting the halogenated hydrocarbon group are the same as the halogen atoms as substituents described above.

[0109] Examples of substituents include groups in which a portion of the hydrocarbon group or the halogenated hydrocarbon group is substituted with at least one atom selected from oxygen and sulfur atoms.

[0110] The amino group used as a substituent may be a primary, secondary, or tertiary amino group. Examples of substituents on secondary and tertiary amino groups include monovalent hydrocarbon groups having 1 to 20 carbon atoms. Monovalent hydrocarbon groups having 1 to 20 carbon atoms are as described above.

[0111] In a group consisting of an amine salt as a substituent, the anion constituting the anionic moiety is, for example, Cl - Examples of well-known anions include the following.

[0112] R 1The substituents that the group represented by may have are, from the viewpoint of excellent polymerization reactivity in the synthesis of component (D-1), preferably a halogen atom, a hydrocarbon group having 1 to 6 carbon atoms, a halogenated hydrocarbon group having 1 to 6 carbon atoms, a nitro group, a cyano group, an amino group, or a salt of an amine, more preferably a fluorine atom, a chlorine atom, a methyl group, a tert-butyl group, a phenyl group, a nitro group, a cyano group, or a primary amino group, and even more preferably a phenyl group.

[0113] In particular, from the viewpoint of achieving the desired effects of the present invention, R 1 The group represented by is preferably without substituents or has a phenyl group as a substituent.

[0114] R 1 Two binding sites (X) in the group represented by 1 The position of the binding site (which binds to etc.) is not particularly limited, but the meta position is preferred from the viewpoint of excellent polymerization reactivity in the synthesis of component (D-1). 1 If is a divalent group consisting of a pyrimidine ring which may have substituents, for example, it is preferable to have a bonding site at the 4th and 6th carbons of the pyrimidine ring. Also, in such a case, R 1 In the group represented by , it is preferable that the substituent is located at the carbon atom at position 2 of the pyrimidine ring.

[0115] In equation (D1-1), R 2 Each of these independently represents a divalent organic group. 2 The group represented by may contain heteroatoms such as oxygen atoms, nitrogen atoms, and sulfur atoms. Among them, R 2 The group represented by preferably contains the group represented by the following formula (D1-2).

[0116] [ka]

[0117] (In formula (D1-2), Ar 1 and Ar2 Each of these independently represents a divalent aromatic group which may have substituents, Each L independently represents a single bond or a divalent linking group. R 4 and R 5 Each of these independently represents a single bond or an alkylene group with 1 to 4 carbon atoms. m1 represents an integer between 0 and 5. The wavy line indicates a connection point.

[0118] In equation (D1-2), Ar 1 and Ar 2 Each of these independently represents a divalent aromatic group which may have substituents. Among them, Ar 1 and Ar 2 Preferably, is a divalent aromatic group having 6 to 30 carbon atoms, more preferably a phenylene group, naphthylene group, anthracenylene group, or biphenylene group (-C6H4-C6H4-), and even more preferably a phenylene group or a naphthylene group.

[0119] Ar 1 and Ar 2 Examples of substituents that can be present include halogen atoms, monovalent hydrocarbon groups having 1 to 20 carbon atoms, halogenated hydrocarbon groups having 1 to 20 carbon atoms, alkoxy groups having 1 to 20 carbon atoms, alkylthio groups having 1 to 20 carbon atoms, nitro groups, cyano groups, carboxyl groups, sulfo groups, phosphono groups, phosphoric acid groups, hydroxyl groups, or primary to tertiary amino groups. The halogen atoms as substituents are as described above. Among these, monovalent hydrocarbon groups having 1 to 20 carbon atoms are preferred as substituents, and one or more substituents selected from methyl groups, vinyl groups, and allyl groups are more preferred.

[0120] Ar 1 and Ar 2 The number of substituents that may be present is preferably 0 or 1 to 8, more preferably 0 or 1 to 4, and even more preferably 0, 1 or 2.

[0121] In formula (D1-2), L independently represents a single bond or a divalent linking group. Examples of divalent linking groups represented by L include divalent groups consisting of one or more skeletal atoms selected from carbon, oxygen, nitrogen, and sulfur atoms (e.g., 1 to 3000, 1 to 1000, 1 to 100, 1 to 50). Examples of divalent linking groups include alkylene groups, alkenylene groups, arylene groups, heteroarylene groups, -O-, -C(=O)-, -C(=O)-O-, and -N(R 6 )-(wherein, R 6 L represents a hydrogen atom, a monovalent hydrocarbon group having 1 to 20 carbon atoms, or a monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms. Examples include -C(=O)-NH-, -NC(=O)N-, -S-, -S(=O)-, -S(O)2-, etc., and may also be a group formed by combining multiple of these. In particular, L is preferably a single bond, -O-, -C(=O)-, -C(=O)-O-, -S-, -S(O)2-, or a divalent group represented by the following formulas (D1-3-1) to (D1-3-4), and more preferably a divalent group represented by the following formulas (D1-4-1) to (D1-4-3).

[0122] [ka]

[0123] (In formulas (D1-3-1) to (D1-3-4), R D11 Each of these independently represents a monovalent group selected from a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, an aryl group having 6 to 14 carbon atoms, and an arylalkyl group having 7 to 15 carbon atoms. R D12 Each of these independently represents a monovalent group selected from a halogen atom, an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, a cycloalkoxy group having 3 to 12 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an aryl group having 6 to 14 carbon atoms, an aryloxy group having 6 to 14 carbon atoms, an arylalkyl group having 7 to 15 carbon atoms, and an arylalkyloxy group having 7 to 15 carbon atoms. m² represents an integer between 1 and 10. m3 represents an integer between 2 and 7. m4 and m5 each independently represent integers between 0 and 4. The wavy line indicates a connection point.

[0124] [ka]

[0125] (In formulas (D1-4-1) to (D1-4-3), R D21 Each of these independently represents a monovalent group selected from a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 14 carbon atoms. R D22 Each of these independently represents a monovalent group selected from alkyl groups with 1 to 4 carbon atoms and aryl groups with 6 to 14 carbon atoms. m6 and m7 each independently represent integers from 0 to 4. The wavy line indicates a connection point.

[0126] In equations (D1-3-1) to (D1-3-3), R D11 Each of these independently represents a monovalent group selected from a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, an aryl group having 6 to 14 carbon atoms, and an arylalkyl group having 7 to 15 carbon atoms. Also, in formula (A1-3-4), R D12 Each of these independently represents a monovalent group selected from a halogen atom, an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, a cycloalkoxy group having 3 to 12 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an aryl group having 6 to 14 carbon atoms, an aryloxy group having 6 to 14 carbon atoms, an arylalkyl group having 7 to 15 carbon atoms, and an arylalkyloxy group having 7 to 15 carbon atoms.

[0127] R D11 or R D12Examples of alkyl groups with 1 to 12 carbon atoms represented by this formula include methyl, ethyl, propyl, and butyl groups.

[0128] R D11 or R D12 Examples of aryl groups with 6 to 14 carbon atoms represented by this formula include phenyl groups, naphthyl groups, anthracenyl groups, and biphenyl groups (-C6H4-C6H5).

[0129] R D11 or R D12 Examples of arylalkyl groups having 7 to 15 carbon atoms, as represented by this formula, include the benzyl group and the phenylethyl group.

[0130] R D12 Examples of alkoxy groups with 1 to 10 carbon atoms represented by this formula include methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, heptoxy, and octoxy groups.

[0131] R D12 Examples of cycloalkyl groups having 3 to 12 carbon atoms, represented by , include cyclopropyl, cyclobutyl, cyclobutyl, cyclopentyl, and cyclohexyl groups.

[0132] R D12 Examples of cycloalkoxy groups with 3 to 12 carbon atoms represented by this formula include cyclopropyloxy group, cyclobutyloxy group, and cyclobutyloxy group.

[0133] R D12 Examples of alkenyl groups with 2 to 10 carbon atoms represented by this formula include methenyl, ethenyl, and propenyl groups.

[0134] R D12 Examples of aryloxy groups with 6 to 14 carbon atoms represented by this formula include phenyloxy groups and naphthyloxy groups.

[0135] R D12Examples of arylalkyloxy groups having 7 to 15 carbon atoms, as represented by this formula, include benzyloxy groups and phenylethyloxy groups.

[0136] In formula (D1-3-1), m2 represents an integer between 1 and 10, preferably an integer between 1 and 6.

[0137] In formula (D1-3-3), m3 represents an integer between 2 and 7, preferably 4 or 5.

[0138] In formula (D1-3-4), m4 and m5 each independently represent integers between 0 and 4, preferably 0 or 1, and more preferably 0.

[0139] In equations (D1-4-1) to (D1-4-3), R D21 Each of these independently represents a monovalent group selected from a hydrogen atom, an alkyl group with 1 to 4 carbon atoms, and an aryl group with 6 to 14 carbon atoms. D22 Each of these independently represents a monovalent group selected from alkyl groups having 1 to 4 carbon atoms and aryl groups having 6 to 14 carbon atoms.

[0140] R D21 or R D22 Examples of alkyl groups with 1 to 4 carbon atoms represented by this formula include methyl, ethyl, propyl, and butyl groups.

[0141] R D21 or R D22 Examples of aryl groups with 6 to 14 carbon atoms represented by this formula include phenyl groups and naphthyl groups.

[0142] In formula (D1-4-3), m6 and m7 each independently represent integers between 0 and 4, preferably 0 or 1, and more preferably 0.

[0143] In formula (D1-2), the divalent linking group represented by L may have R 6This represents a hydrogen atom, a monovalent hydrocarbon group having 1 to 20 carbon atoms, or a monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms.

[0144] R 6 As a monovalent hydrocarbon group having 1 to 20 carbon atoms, R 1 This is similar to the "monovalent hydrocarbon group with 1 to 20 carbon atoms" as a substituent that the group represented by can have.

[0145] R 6 As a monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms, R 1 This is similar to the "monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms" as a substituent that the group represented by can have.

[0146] In equation (D1-2), R 4 and R 5 Each of these independently represents a single bond or an alkylene group with 1 to 4 carbon atoms. Examples of alkylene groups with 1 to 4 carbon atoms include methylene, ethylene, n-propylene, isopropylene, n-butylene, and sec-butylene groups. Among these, R 4 and R 5 The group represented is preferably a single bond, a methylene group, or an ethylene group.

[0147] In equation (D1-2), m1 represents an integer between 0 and 5, preferably between 0 and 4, and more preferably between 0 and 3.

[0148] In equation (D1-1), X 1 These are, independently, -O-, -S-, or -N(R 3 ) represents X 1 The group represented by R may have 3 X represents a hydrogen atom, a monovalent hydrocarbon group having 1 to 20 carbon atoms, a monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms, or a group in which the hydrocarbon group or a part of the halogenated hydrocarbon group is substituted with at least one atom selected from oxygen and sulfur atoms. Note that two or more X 1 However, each of them is -N(R 3)- If X 1 The group represented by has R 3 These may be the same or they may be different.

[0149] R 3 As a monovalent hydrocarbon group having 1 to 20 carbon atoms represented by formula (D1-1), R 1 This is similar to the "monovalent hydrocarbon group with 1 to 20 carbon atoms" as a substituent that the group represented by can have.

[0150] R 3 As a monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms represented by formula (D1-1), R 1 This is similar to the "monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms" as a substituent that the group represented by can have.

[0151] R 3 The "group in which a part of the hydrocarbon group or the halogenated hydrocarbon group is substituted with at least one selected from oxygen atoms and sulfur atoms" represented by formula (D1-1) is R 1 The substituents that the group represented by can have are the same as "a group in which a part of the hydrocarbon group or the halogenated hydrocarbon group is substituted with at least one selected from an oxygen atom and a sulfur atom."

[0152] In formula (y), Y represents a monovalent organic group having 3 to 50 carbon atoms that contains a radical polymerizable group other than a maleimide group.

[0153] Examples of radical polymerizable groups that the group represented by Y may possess include vinyl group, 1-propenyl group, allyl group (2-propenyl group), isopropenyl group, vinylphenyl group, styryl group, (meth)acryloyl group, fumaroyl group, and the like.

[0154] The group represented by Y may contain only radical polymerizable groups, or it may contain radical polymerizable groups via divalent linking groups. Examples of divalent linking groups include alkylene groups, alkenylene groups, arylene groups, heteroarylene groups, -O-, -C(=O)-, -C(=O)-O-, -NH-, -C(=O)-NH-, -NC(=O)N-, -S-, -S(=O)-, -S(O)2-, etc., and may also be a group formed by combining multiple of these. Among these, alkylene groups are preferred as divalent linking groups, and methylene groups are more preferred.

[0155] In one preferred embodiment, the group represented by Y contains a monovalent aromatic group containing a radical polymerizable group. More preferably, the group represented by Y is a monovalent group selected from vinylphenyl, allylphenyl, isopropenylphenyl, and vinylbenzyl groups, with vinylbenzyl being even more preferred.

[0156] In one preferred embodiment, component (D-1) contains a group represented by Y via a divalent linking group. In particular, component (D-1) preferably contains at least one of the terminal groups represented by the following formulas (D1-5-1) and (D1-5-2).

[0157] [ka]

[0158] (In formulas (D1-5-1) and (D1-5-2), X D1 These are single bonds, -O-, -S-, or -N(R) 3 )- represents; The other symbols are as described above.

[0159] In equations (D1-5-1) and (D1-5-2), X D1 These are single bonds, -O-, -S-, or -N(R) 3 ) represents X D1 The group represented by R may have 3 The details are as described above.

[0160] Component (D-1) may be synthesized by known methods. Component (D-1) may be, for example, R 1 Compounds that serve as raw materials for structures containing the group represented by R 2 The compounds that serve as raw materials for structures containing the group represented by , the compounds that serve as raw materials for structures containing the group represented by Y, and, if necessary, compounds that derive other structural units, can be synthesized by heating them together in an organic solvent with alkali metals or alkali metal compounds (and, if necessary, polymerization inhibitors). The compounds that serve as raw materials for structures containing the group represented by Y, and the compounds that derive other structural units (structural units other than structural unit (1)), are R 1 Compounds that serve as raw materials for structures containing the group represented by R 2 The compounds that serve as raw materials for a structure containing the group represented by may be reacted, and then heated, mixed, and reacted.

[0161] In the synthesis of component (D-1), R 1Examples of compounds that serve as raw materials for structures containing the group represented by include 4,6-dichloropyrimidine, 4,6-dibromopyrimidine, 2,4-dichloropyrimidine, 2,5-dichloropyrimidine, 2,5-dibromopyrimidine, 5-bromo-2-chloropyrimidine, 5-bromo-2-fluoropyrimidine, 5-bromo-2-iodopyrimidine, 2-chloro-5-fluoropyrimidine, and 2-chloro-5-iodopyrimidine. Zin, 2-phenyl-4,6-dichloropyrimidine, 2-methylthio-4,6-dichloropyrimidine, 2-methylsulfonyl-4,6-dichloropyrimidine, 5-methyl-4,6-dichloropyrimidine, 2-amino-4,6-dichloropyrimidine, 5-amino-4,6-dichloropyrimidine, 2,5-diamino-4,6-dichloropyrimidine, 4-amino-2,6-dichloropyrimidine, 5-methoxy-4, 6-Dichloropyrimidine, 5-Methoxy-2,4-Dichloropyrimidine, 2-Methyl-4,6-Dichloropyrimidine, 6-Methyl-2,4-Dichloropyrimidine, 5-Methyl-2,4-Dichloropyrimidine, 5-Nitro-2,4-Dichloropyrimidine, 4-Amino-2-Chloro-5-Fluoropyrimidine, 2-Methyl-5-Amino-4,6-Dichloropyrimidine, 5-Bromo-4-Chloro-2-Methylthiopyrimidine Examples include pyrimidine compounds such as limidine; pyridazine compounds such as 3,6-dichloropyridazine, 3,5-dichloropyridazine, and 4-methyl-3,6-dichloropyridazine; and pyrazine compounds such as 2,3-dichloropyrazine, 2,6-dichloropyrazine, 2,5-dibromopyrazine, 2,6-dibromopyrazine, 2-amino-3,5-dibromopyrazine, and 5,6-dicyano-2,3-dichloropyrazine. These compounds may be used individually or in combination of two or more.

[0162] In the synthesis of component (D-1), R 2Compounds that serve as raw materials for structures containing the group represented by include, for example, dihydroxyphenyl compounds such as hydroquinone, resorcinol, catechol, and phenylhydroquinone; 9,9-bis(4-hydroxyphenyl)fluorene, 9,9-bis(4-hydroxy-3-methylphenyl)fluorene, 9,9-bis(4-hydroxy-3-phenylphenyl)fluorene, 1,1-bis(4-hydroxyphenyl)-1-phenylethane, bis(4-hydroxyphenyl)diphenylmethane, 2,2-bis(4-hydroxyphenyl)propane, 2,2-bis(4-hydroxy-3-allylphenyl)propane, 2,2-bis(4-hydroxy-3-methylphenyl)propane, 2,2-bis(4-hydroxy-3-phenylphenyl)propane, 4,4'-(1,3-dimethylbutylidene)bisphenol, 1,1-bis(4-hydroxyphenyl)-nonane, bis(4-hydroxyphenyl)sulfone, 1,1-bis(4-hydroxyphenyl) Roxyphenyl)cyclohexane, 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane, 1,1-bis(3-methyl-4-hydroxyphenyl)-3,3,5-trimethylcyclohexane, 1,1-bis(3-cyclohexyl-4-hydroxyphenyl)-3,3,5-trimethylcyclohexane, 1,4-bis[2-(4-hydroxyphenyl)-2-propyl]benzene, 1,3-bis[2-(4-hydroxyphenyl)-2 Examples include bisphenol compounds such as -propyl]benzene, 4,4'-cyclododecylidenebisphenol, 4,4'-decylidenebisphenol, and 4,4'-dihydroxy-2,2',3,3',5,5'-hexamethylbiphenyl; and diol compounds such as "Priplast 1901," "Priplast 1838," "Priplast 3186," "Priplast 3192," "Priplast 3197," and "Priplast 3199" manufactured by Croda Japan. These compounds may be used individually or in combination of two or more.

[0163] (D-1) In the synthesis of component (D-1), examples of compounds that serve as raw materials for structures containing the group represented by Y include monovalent phenol compounds such as 4-isopropenylphenol, 4-vinylphenol, 2-allylphenol, isoeugenol, and tocotrienol; monovalent amine compounds such as diallylamine; monovalent thiol compounds such as 2-propene-1-thiol; monovalent aliphatic halides such as allyl chloride, 4-(chloromethyl)styrene, and 3-(chloromethyl)styrene; monovalent acid halides such as acrylic chloride, methacrylic chloride, crotonoyl chloride, and cinnamoyl chloride; and monovalent acid anhydrides such as acrylic anhydride, crotonic anhydride, and methacrylic anhydride. These compounds may be used individually or in combination of two or more.

[0164] If component (D-1) contains other structural units (structural units other than structural unit (1)), examples of compounds that induce such other structural units include compounds that induce structural units containing carbonate bonds, thiocarbonate bonds, or selenocarbonate bonds, such as diphenyl carbonate, diphenylthiocarbonate, diphenylselenocarbonate, phosgene, thiophosgene, and selenophosgene; dihydroxy compounds such as benzenedimethanol and cyclohexanedimethanol; phosphine oxide compounds such as bis(fluorophenyl)phenylphosphine oxide, bis(fluorophenyl)naphthylphosphine oxide, and bis(fluorophenyl)anthrylphosphine oxide; and dihalides of dicarboxylic acids such as phthalate dichloride, isophthalate dichloride, and terephthalate dichloride. These compounds may be used individually or in combination of two or more.

[0165] In the synthesis of component (D-1), when a compound having a hydroxyl group, such as a phenol compound, is used as a raw material, the alkali metal and alkali metal compound react with the compound having a hydroxyl group to form an alkali metal salt. Examples of such alkali metals and alkali metal compounds include alkali metals such as lithium, sodium, and potassium; alkali metal hydrides such as lithium hydride, sodium hydride, and potassium hydride; alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, and potassium hydroxide; alkali metal carbonates such as lithium carbonate, sodium carbonate, and potassium carbonate; and alkali metal bicarbonates such as lithium bicarbonate, sodium bicarbonate, and potassium bicarbonate. Among these, alkali metal carbonates are preferred, and potassium carbonate is more preferred.

[0166] In the synthesis of component (D-1), suitable organic solvents include, for example, ether-based solvents such as tetrahydrofuran (THF), dioxane, cyclopentyl methyl ether, anisole, phenethole, diphenyl ether, dialkoxybenzene, and trialkoxybenzene; nitrogen-containing solvents such as N,N-dimethylacetamide (DMAc), N,N-dimethylformamide, N-methyl-2-pyrrolidone, and 1,3-dimethyl-2-imidazolidinone; ester-based solvents such as γ-butyrolactone; sulfur-containing solvents such as sulfolane, dimethyl sulfoxide, diethyl sulfoxide, dimethyl sulfone, diethyl sulfone, diisopropyl sulfone, and diphenyl sulfone; ketone-based solvents such as benzophenone, 2-heptanone, cyclohexanone, and methyl ethyl ketone; halogen-based solvents such as methylene chloride, chloroform, and chlorobenzene; and aromatic hydrocarbon solvents such as benzene, toluene, and xylene. Among these, 2-heptanone, cyclohexanone, N-methyl-2-pyrrolidone, toluene, and / or xylene are preferred, and N-methyl-2-pyrrolidone, 2-heptanone, and / or cyclohexanone are more preferred.

[0167] In the synthesis of component (D-1), polymerization inhibitors may be used to control the polymerization reaction and obtain component (A-1) having the desired molecular weight. Examples of polymerization inhibitors include quinones, hindered phenol compounds, and amine compounds.

[0168] Examples of quinones used as polymerization inhibitors include p-benzoquinone, 2-t-butyl-p-benzoquinone, 2,5-diphenyl-p-benzoquinone, chloranil, and trimethylquinone.

[0169] Examples of hindered phenol compounds used as polymerization inhibitors include 1,6-hexanediol-bis[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate], 2,4-bis-(n-octylthio)-6-(4-hydroxy-3,5-di-t-butylanilino)-3,5-triazine, pentaerythritol tetrakis[3-(3,5-t-butyl-4-hydroxyphenyl)propionate], 2,2-thio-diethylenebis[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate], and octadecyl-3-(3,5-di-t-butyl Examples include (-4-hydroxyphenyl)propionate, tris-(3,5-di-t-butyl-4-hydroxybenzyl)-isocyanurate, 2,6-di-tert-butyl-p-cresol (BHT), 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione, and 1,3,5-tris(3,5-di-tert-butyl-4-hydroxyphenylmethyl)-2,4,6-trimethylbenzene. As polymerization inhibitors, commercially available hindered phenol compounds may be used, such as "AO-20" and "AO-330" manufactured by ADEKA.

[0170] Examples of amine compounds used as polymerization inhibitors include phenothiazine, 3,7-dicumylphenothiazine, N,N'-diphenyl-1,4-phenylenediamine, and N,N'-di-2-naphthyl-1,4-phenylenediamine.

[0171] In the synthesis of component (D-1), R 1 Compounds that serve as raw materials for structures containing the group represented by R 2 The reaction temperature when reacting the compounds that serve as raw materials for a structure containing the group represented by is preferably 50°C or higher, more preferably 80°C or higher, preferably 300°C or lower, and more preferably 200°C or lower. The reaction time in the reaction is preferably 1 hour or more, more preferably 2 hours or more, even more preferably 3 hours or more, preferably 100 hours or less, more preferably 50 hours or less, and even more preferably 25 hours or less.

[0172] In the synthesis of component (D-1), R 1 Compounds that serve as raw materials for structures containing the group represented by R 2 When a compound that serves as a raw material for a structure containing the group represented by is reacted, and then a compound that serves as a raw material for a structure containing the group represented by Y (and, if necessary, a compound that derives other structural units) is reacted, the reaction temperature is preferably 0°C or higher, more preferably 10°C or higher, preferably 130°C or lower, and more preferably 110°C or lower. The reaction time in this reaction is preferably 1 hour or more, more preferably 2 hours or more, even more preferably 3 hours or more, preferably 50 hours or less, more preferably 25 hours or less, and even more preferably 15 hours or less.

[0173] The weight-average molecular weight (Mw) of component (D-1) is, for example, 100 or more, preferably 1,000 or more, more preferably 1,500 or more, even more preferably 2,000 or more, 2,500 or more, or 3,000 or more. The upper limit of the weight-average molecular weight (Mw) of component (D-1) is, for example, 500,000 or less, preferably 100,000 or less, more preferably 10,000 or less, even more preferably 6,000 or less, 5,000 or less, or 4,500 or less. The weight-average molecular weight (Mw) of component (D-1) can be measured as a polystyrene equivalent value by gel permeation chromatography (GPC).

[0174] The content of structural unit (1) in component (D-1) is preferably 30 mol% or more, more preferably 50 mol% or more, even more preferably 60 mol% or more, preferably 99.5 mol% or less, more preferably 98 mol% or less, and even more preferably 95 mol% or less, when the total amount of structural units contained in component (D-1) is taken as 100 mol%.

[0175] The resin composition of the present invention may contain a combination of components (D-1), (D-2), and (D-3). The content of component (D) contained in the resin composition of the present invention is, from the viewpoint of achieving the desired effects of the present invention, preferably 3% by mass or more, more preferably 5% by mass or more, even more preferably 7% by mass or more, 10% by mass or more, preferably 28% by mass or less, more preferably 26% by mass or less, and even more preferably 24% by mass or less, based on 100% by mass of nonvolatile components in the resin composition.

[0176] The ratio of the content of component (A) to the content of component (D) in the resin composition [(A) component / (D) component] is preferably 0.001 or more, more preferably 0.0015 or more, and even more preferably 0.002 or more, from the viewpoint of achieving the desired effects of the present invention, and the upper limit of the total amount is preferably 0.05 or less, more preferably 0.03 or less, and even more preferably 0.025 or less.

[0177] The ratio of the content of component (A) in the resin composition to the total content of components (C) and (D) {component (A) / [component (C)+component (D)]} is preferably 0.0004 or more, more preferably 0.0006 or more, and even more preferably 0.0009 or more, from the viewpoint of minimizing plating penetration. The upper limit is preferably 0.015 or less, more preferably 0.013 or less, and even more preferably 0.012 or less or 0.0115 or less.

[0178] The ratio of the content of component (A) in the resin composition to the total content of components (C), (D), and (F) {(A) component / [(C) component + (D) component + (F) component]} is preferably 0.0003 or more, more preferably 0.0005 or more, and even more preferably 0.0007 or more, from the viewpoint of minimizing plating penetration. The upper limit is preferably 0.015 or less, more preferably 0.013 or less, and even more preferably 0.012 or less or 0.011 or less.

[0179] The ratio of the content of component (C) to the content of component (D) in the resin composition [(C) component / (D) component] is preferably 0.05 or higher, more preferably 0.08 or higher, and even more preferably 0.011 or higher or 0.115 or higher, from the viewpoint of reducing the dielectric loss tangent (Air, N2) while also having excellent adhesion to the substrate. The upper limit is preferably 3 or lower, more preferably 2.7 or lower, and even more preferably 2.5 or lower or 2.4 or lower.

[0180] <(E) Curing accelerator> The resin composition according to the first embodiment of the present invention may contain (E) a curing accelerator. Unless otherwise specified, the (E) curing accelerator does not include components (A) to (D) described above. The (E) curing accelerator can accelerate the curing of the resin composition. The (E) curing accelerator may be used alone or in combination of two or more types.

[0181] Examples of curing accelerators include imidazole-based curing accelerators, phosphorus-based curing accelerators, amine-based curing accelerators, guanidine-based curing accelerators, metal-based curing accelerators, and urea-based curing accelerators. In addition, thermal radical polymerization initiators such as peroxide-based radical polymerization initiators and azo-based radical polymerization initiators may be used as curing accelerators. In particular, (E) the curing accelerator preferably contains at least one of an imidazole-based curing accelerator, a phosphorus-based curing accelerator, a peroxide radical polymerization initiator, and an azo-based radical polymerization initiator, and more preferably contains an imidazole-based curing accelerator.

[0182] Examples of imidazole-based curing accelerators include 2-methylimidazole, 2-undecylimidazole, 2-heptadecylimidazole, 1,2-dimethylimidazole, 2-ethyl-4-methylimidazole, 1,2-dimethylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 2-phenyl-4-methylimidazole, 1-benzyl-2-methylimidazole, 1-benzyl-2-phenylimidazole, 1-Cyanoethyl-2-methylimidazole, 1-Cyanoethyl-2-undecylimidazole, 1-Cyanoethyl-2-ethyl-4-methylimidazole, 1-Cyanoethyl-2-phenylimidazole, 1-Cyanoethyl-2-undecylimidazolium trimellitate, 1-Cyanoethyl-2-phenylimidazolium trimellitate, 2,4-Diamino-6-[2'-methylimidazolyl-(1')]-ethyl-s-triazine, 2, 4-diamino-6-[2'-undecylimidazolyl-(1')]-ethyl-s-triazine, 2,4-diamino-6-[2'-ethyl-4'-methylimidazolyl-(1')]-ethyl-s-triazine, 2,4-diamino-6-[2'-methylimidazolyl-(1')]-ethyl-s-triazine isocyanurate adduct, 2-phenylimidazole isocyanurate adduct, 2-phenyl-4,5-dihydroxymethylimidazole, 2-F Examples include imidazole compounds such as phenyl-4-methyl-5-hydroxymethylimidazole, 2,3-dihydro-1H-pyrrolo[1,2-a]benzimidazole, 1-dodecyl-2-methyl-3-benzylimidazolium chloride, 2-methylimidazoline, and 2-phenylimidazoline, as well as adducts of imidazole compounds with epoxy resins, with 2-ethyl-4-methylimidazole and 1-benzyl-2-phenylimidazole being preferred.Commercially available imidazole-based curing accelerators may be used, for example, "P200-H50" from Mitsubishi Chemical Corporation; and "Curesol 2MZ", "2E4MZ", "Cl1Z", "Cl1Z-CN", "Cl1Z-CNS", "Cl1Z-A", "2MZ-OK", "2MA-OK", "2MA-OK-PW", "2MZA-PW", "2PHZ", "2PHZ-PW", "2P4MZ", "1B2PZ", "1B2PZ-10M" from Shikoku Chemicals, Inc.

[0183] Examples of phosphorus-based curing accelerators include phosphonium salts and phosphines. Examples of phosphonium salts include aliphatic phosphonium salts such as tetrabutylphosphonium bromide, tetrabutylphosphonium chloride, tetrabutylphosphonium acetate, tetrabutylphosphonium decanoate, tetrabutylphosphonium laurate, n-butylphosphonium tetraphenylborate, bis(tetrabutylphosphonium) pyromelitate, tetrabutylphosphonium hydrogen hexahydrophthalate, tetrabutylphosphonium 2,6-bis[(2-hydroxy-5-methylphenyl)methyl]-4-methylphenolate, and di-tert-butylmethylphosphonium tetraphenylborate; methyltriphenylphosphonium bromide, ethyltriphenylphosphonium bromide, and propyltriphenylphosphonium. Examples include bromide, butyltriphenylphosphonium bromide, benzyltriphenylphosphonium chloride, tetraphenylphosphonium bromide, p-tolyltriphenylphosphonium tetra-p-tolylborate, tetraphenylphosphonium tetraphenylborate, tetraphenylphosphonium tetra-p-tolylborate, triphenylethylphosphonium tetraphenylborate, tris(3-methylphenyl)ethylphosphonium tetraphenylborate, tris(2-methoxyphenyl)ethylphosphonium tetraphenylborate, (4-methylphenyl)triphenylphosphonium thiocyanate, tetraphenylphosphonium thiocyanate, butyltriphenylphosphonium thiocyanate, and other aromatic phosphonium salts.

[0184] Examples of phosphines include aliphatic phosphines such as tributylphosphine, tri-tert-butylphosphine, trioctylphosphine, di-tert-butyl(2-butenyl)phosphine, di-tert-butyl(3-methyl-2-butenyl)phosphine, tricyclohexylphosphine; dibutylphenylphosphine, di-tert-butylphenylphosphine, methyldiphenylphosphine, ethyldiphenylphosphine, butyldiphenylphosphine, diphenylcyclohexylphosphine, triphenylphosphine, tri-o-tolylphosphine, tri-m-tolylphosphine, tri-p-tolylphosphine, tris(4-ethylphenyl)phosphine, tris(4-propylphenyl)phosphine, tris(4-isopropylphenyl)phosphine, tris(4-butylphenyl)phosphine, tris(4-tert-butylphenyl)phosphine, tris(2,4-dimethylphenyl)phosphine, and tris(2,5-dimethylphenyl)phosphine. Tris(2,6-dimethylphenyl)phosphine, 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- Examples include aromatic phosphines such as 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; aromatic phosphine-borane complexes such as triphenylphosphine and triphenylborane; and aromatic phosphine-quinone addition products such as triphenylphosphine-p-benzoquinone addition products.

[0185] As a phosphorus-based curing accelerator, commercially available products may be used, such as "TBP-DA" manufactured by Hokko Chemical Industry Co., Ltd.

[0186] Examples of amine-based curing accelerators include trialkylamines such as triethylamine and tributylamine, 4-dimethylaminopyridine, benzyldimethylamine, 2,4,6-tris(dimethylaminomethyl)phenol, 1,8-diazabicyclo(5,4,0)-undecene, 1,8-diazabicyclo[5,4,0]undecene-7,4-dimethylaminopyridine, and 2,4,6-tris(dimethylaminomethyl)phenol, with 4-dimethylaminopyridine being preferred. Commercially available amine-based curing accelerators may also be used, such as "PN-50," "PN-23," and "MY-25" manufactured by Ajinomoto Fine Techno Co., Ltd.

[0187] 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]deca-5-ene, and 7-methyl-1,5,7-triazabicyclo[4.4.0]deca-5-ene. Examples include ro[4.4.0]deca-5-ene, 1-methyl biguanide, 1-ethyl biguanide, 1-n-butyl biguanide, 1-n-octadecyl biguanide, 1,1-dimethyl biguanide, 1,1-diethyl biguanide, 1-cyclohexyl biguanide, 1-allyl biguanide, 1-phenyl biguanide, 1-(o-tolyl) biguanide, and the like, with dicyandiamide and 1,5,7-triazabicyclo[4.4.0]deca-5-ene being preferred.

[0188] Examples of metal-based hardening 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 organocobalt complexes such as cobalt(II) acetylacetonate and cobalt(III) acetylacetonate, organocopper complexes such as copper(II) acetylacetonate, organozinc complexes such as zinc(II) acetylacetonate, organoiron complexes such as iron(III) acetylacetonate, organonickel complexes such as nickel(II) acetylacetonate, and organomanganese complexes such as manganese(II) acetylacetonate. Examples of organometallic salts include zinc octoate, tin octoate, zinc naphthenate, cobalt naphthenate, tin stearate, and zinc stearate.

[0189] Examples of urea-based curing accelerators include aliphatic dimethylureas such as 1,1-dimethylurea, 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)-1,1-dimethylurea. Aromatic dimethylureas such as toluenebisdimethylurea, 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] are examples.

[0190] Examples of benzotriazole-based curing accelerators include 1,2,3-benzotriazole, 1-[N,N-bis(2-ethylhexyl)aminomethyl]benzotriazole, carboxybenzotriazole, carboxybenzotriazole, 1-[N,N-bis(2-ethylhexyl)aminomethyl]methylbenzotriazole, 2,2'-[[(methyl-1H-benzotriazole-1-yl)methyl]imino]bisethanol, aqueous solution of 1,2,3-benzotriazole sodium salt, tolyltriazole, and the like. As a benzotriazole-based curing accelerator, commercially available products may be used, such as "BT-120" manufactured by Johoku Chemical Co., Ltd.

[0191] Examples of tetrazole-based curing accelerators include 5-benzyl-1H-tetrazole and 5-amino-1-methyltetrazole.

[0192] Examples of peroxide-based radical polymerization initiators include hydroperoxide compounds such as 1,1,3,3-tetramethylbutyl hydroperoxide; dialkylperoxide compounds such as tert-butylcumyl peroxide, di-tert-butyl peroxide, di-tert-hexyl peroxide, di-tert-amyl peroxide, dicumyl peroxide, 1,4-bis(1-tert-butylperoxy-1-methylethyl)benzene, and 2,5-dimethyl-2,5-bis(tert-butylperoxy)hexane; and dialkyl peroxide compounds such as dilauroyl peroxide, didecanoyl peroxide, dicyclohexyl peroxydicarbonate, and bis(4-tert-butylcyclohexyl) peroxydicarbonate. Examples of peroxyester compounds include tert-butyl peroxyacetate, tert-butyl peroxybenzoate, tert-butyl peroxyisopropyl monocarbonate, tert-butyl peroxy-2-ethylhexanoate, tert-butyl peroxyneodecanoate, tert-hexyl peroxyisopropyl monocarbonate, tert-butyl peroxylaurate, (1,1-dimethylpropyl)2-ethyl perhexanoate, tert-butyl 2-ethyl perhexanoate, tert-butyl 3,5,5-trimethyl perhexanoate, tert-butyl peroxy-2-ethylhexyl monocarbonate, tert-butyl peroxymaleic acid, and other peroxyester compounds. Commercial peroxide-based radical polymerization initiators may be used, such as "Perbutyl C" manufactured by NOF Corporation.

[0193] Examples of azo radical polymerization initiators include azonitrile compounds such as 2,2'-azobis(4-methoxy-2,4-dimethylvaleronitrile), 2,2'-azobis(2,4-dimethylvaleronitrile), 2,2'-azobisisobutyronitrile, 2,2'-azobis(2-methylbutyronitrile), 1,1'-azobis(cyclohexane-1-carbonitride), 1-[(1-cyano-1-methylethyl)azo]formamide, and 2-phenylazo-4-methoxy-2,4-dimethylvaleronitrile; 2,2'-azobis[2-methyl-N-[1,1-bis(hydroxymethyl)-2-hydroxyethyl]propionamide], and 2,2'-azobis[2-methyl-N-[1,1-bis(hydroxymethyl)-2-hydroxyethyl]propionamide]. Examples include azoamide compounds such as methyl)ethyl[propionamide], 2,2'-azobis[2-methyl-N-[2-(1-hydroxybutyl)]-propionamide], 2,2'-azobis[2-methyl-N-(2-hydroxyethyl)-propionamide], 2,2'-azobis(2-methylpropionamide) dihydrate, 2,2'-azobis[N-(2-propenyl)-2-methylpropionamide], 2,2'-azobis(N-butyl-2-methylpropionamide), and 2,2'-azobis(N-cyclohexyl-2-methylpropionamide); and alkylazo compounds such as 2,2'-azobis(2,4,4-trimethylpentane) and 2,2'-azobis(2-methylpropane). As an azo radical polymerization initiator, commercially available products may be used, such as "VR-110" manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.

[0194] When the resin composition according to the first embodiment contains (E) a curing accelerator, the content of component (E) in the resin composition is, for example, 0.05% by mass or more, preferably 0.07% by mass or more, more preferably 0.09% by mass or more, preferably 5% by mass or less, more preferably 2% by mass or less, and even more preferably 1% by mass or less, based on 100% by mass of the nonvolatile components in the resin composition.

[0195] <(F) Thermosetting monomer> The resin composition according to the first embodiment of the present invention may contain (F) a thermosetting monomer as an optional component. Unless otherwise specified, the (F) thermosetting monomer does not include components (A) to (E) described above. The (F) thermosetting monomer can react with heat to form bonds and harden. Therefore, by including (A) a TEMPO-based compound, (B) an inorganic filler, (C) a maleimide resin, (D-1) a compound containing a first specific structural unit and a specific end group, and preferably (E) a curing accelerator, the (F) thermosetting monomer functions as a crosslinking agent for polymer components. By curing such a resin composition, an insulating layer containing the cured product of the resin composition can be obtained. The (F) thermosetting monomer may be used alone or in combination of two or more types. (F) The thermosetting monomer may be in solid or liquid form, but it is preferable for it to be liquid at 25°C as it is easier to handle and suitable for the production of resin compositions.

[0196] (F) The thermosetting monomer preferably contains a cyclic structure from the viewpoint of better achieving the desired effects of the present invention. The cyclic structure may be either an aromatic ring or a non-aromatic ring, or it may be a structure in which an aromatic ring and a non-aromatic ring are fused. Examples of structures in which an aromatic ring and a non-aromatic ring are fused include indan rings, fluorene rings, and similar structures to these cyclic structures. The "similar structures to these cyclic structures" include structures in which substituents are bonded to an indan ring or a fluorene ring; structures in which an unsaturated bond is contained in the portion of the indan ring or fluorene ring that forms a non-aromatic ring; and so on. Examples of substituents in "structures in which substituents are bonded to an indan ring or a fluorene ring" include halogen atoms, alkyl groups, alkoxy groups, aryl groups, arylalkyl groups, silyl groups, acyl groups, acyloxy groups, carboxyl groups, sulfo groups, cyano groups, nitro groups, hydroxyl groups, mercapto groups, oxo groups, and so on.

[0197] (F) The thermosetting monomer preferably contains a radical polymerizable group other than a maleimide group, from the viewpoint of better achieving the desired effects of the present invention. Examples of radical polymerizable groups other than a maleimide group include a vinyl group, a 1-propenyl group, an allyl group (2-propenyl group), an isopropenyl group, a vinylphenyl group, a styryl group, a (meth)acryloyl group, a fumaroyl group, and the like.

[0198] In one embodiment, the (F) thermosetting monomer may have reactive groups other than radical polymerizable groups. Examples of such reactive groups include amino groups, cyanate groups, acid anhydride groups, and mercapto groups. In one preferred embodiment, the (F) thermosetting monomer has an amino group.

[0199] (F) From the viewpoint of achieving the desired effects of the present invention, the thermosetting monomer preferably contains one or more functional groups selected from the group consisting of vinyl groups, allyl groups, (meth)acryloyl groups, and amino groups.

[0200] In one preferred embodiment, the (F) thermosetting monomer comprises a resin containing a cyclic structure and one or more functional groups selected from the group consisting of vinyl groups, 1-propenyl groups, allyl groups, (meth)acryloyl groups, and amino groups. In such an embodiment, it is more preferable that the (F) thermosetting monomer comprises a resin containing a cyclic structure and one or more functional groups selected from the group consisting of vinyl groups, allyl groups, (meth)acryloyl groups, and amino groups.

[0201] Examples of resins containing a cyclic structure and vinyl groups include resins having one or more, preferably two or more, vinyl groups directly bonded to an aromatic carbon atom. Examples of such resins include divinylbenzene (DVB), 2,4-divinyltoluene, 2,6-divinylnaphthalene, and 1,4-divinylnaphthalene. Examples of commercially available resins of this type include "MEH-8000H" and "MEH-8005" manufactured by Meiwa Kasei Co., Ltd.

[0202] The resin containing a cyclic structure and an allyl group preferably contains a cyclic structure selected from either a phenol ring or a carboxylic acid derivative containing an aromatic ring and / or a non-aromatic ring.

[0203] Examples of resins containing a phenol ring and an allyl group include cresol resins containing an allyl group, novolac-type phenol resins containing an allyl group, and cresol novolac resins containing an allyl group. Commercially available examples of such resins include "MEH-8000H" and "MEH-8005" manufactured by Meiwa Kasei Co., Ltd.

[0204] In a resin containing a carboxylic acid derivative containing an aromatic ring and / or a non-aromatic ring and an allyl group, examples of carboxylic acids containing an aromatic ring and / or a non-aromatic ring include isocyanuric acid, diphenic acid, phthalic acid, and cyclohexanedicarboxylic acid. Specific examples of resins containing a carboxylic acid derivative containing an aromatic ring and / or a non-aromatic ring and an allyl group include allyl isocyanurate, diallyl isocyanurate, triallyl isocyanurate, diallyl diphenate, allyl diphenate, orthodiallyl phthalate, metadiallyl phthalate, paradiallyl phthalate, allyl cyclohexanedicarboxylic acid, and diallyl cyclohexanedicarboxylic acid. Commercially available resins of this type include "TAIC" (triallyl isocyanurate) from Shinryo Co., Ltd.; "MDAC" (allyl resin with cyclohexanedicarboxylic acid derivative) from Osaka Soda Co., Ltd.; "DAD" (diallyl diphenate) from Nichishoku Techno Fine Chemical Co., Ltd.; and "Daiso Dap Monomer" (orthodiallyl phthalate) from Osaka Soda Co., Ltd.

[0205] In a resin containing a cyclic structure and a (meth)acryloyl group, the cyclic structure is preferably a divalent cyclic group. The divalent cyclic group may be either a divalent aromatic group or a divalent aliphatic group containing a non-aromatic ring. In particular, from the viewpoint of better achieving the desired effects of the present invention, the divalent cyclic group is more preferably a divalent aliphatic group containing a non-aromatic ring.

[0206] From the viewpoint of better achieving the desired effects of the present invention, the divalent cyclic group is preferably a ring with 3 or more members, more preferably a ring with 4 or more members, even more preferably a ring with 5 or more members, preferably a ring with 20 or fewer members, more preferably a ring with 15 or fewer members, and even more preferably a ring with 10 or fewer members. Furthermore, the divalent cyclic group may be a monocyclic or polycyclic structure.

[0207] In a divalent cyclic group, the ring skeleton may be composed of heteroatoms in addition to carbon atoms. Examples of heteroatoms include oxygen atoms, sulfur atoms, nitrogen atoms, etc., with oxygen atoms being preferred. The ring may have one heteroatom or two or more.

[0208] Specific examples of divalent cyclic groups include the following divalent groups (i) to (xi). In the following divalent groups (i) to (xi), the wavy lines indicate the bonding sites. Among these, (x) or (xi) are preferred as divalent cyclic groups.

[0209] [ka]

[0210] The divalent cyclic group may have substituents. Examples of such substituents include halogen atoms, alkyl groups, alkoxy groups, aryl groups, arylalkyl groups, silyl groups, acyl groups, acyloxy groups, carboxyl groups, sulfo groups, cyano groups, nitro groups, hydroxyl groups, mercapto groups, and oxo groups, with alkyl groups being preferred.

[0211] In a resin containing a cyclic structure and a (meth)acryloyl group, the (meth)acryloyl group may be directly bonded to the divalent cyclic group or bonded via a divalent linking group. Examples of divalent linking groups include alkylene groups, alkenylene groups, arylene groups, heteroarylene groups, -C(=O)O-, -O-, -NHC(=O)-, -NC(=O)N-, -NHC(=O)O-, -C(=O)-, -S-, -SO-, -NH-, etc., and may also be groups formed by combining multiple of these groups. Alkylene groups are preferred as divalent linking groups, and methylene groups and 1,1-dimethylethylene groups are particularly preferred.

[0212] The resin containing a cyclic structure and a (meth)acryloyl group is preferably a resin represented by the following formula (F1).

[0213] [ka]

[0214] (In formula (F1), R F1 Each of these independently represents a (meth)acryloyl group; R F2 Each of these independently represents a divalent linking group; Ring F 1 (This indicates a divalent cyclic group.)

[0215] In equation (F1), R F1 Each of these independently represents a (meth)acryloyl group, and it is preferable that they be acryloyl groups.

[0216] In equation (F1), R F2 Each of these independently represents a divalent linking group. F2 The "divalent linking group" indicated by this is the same as the divalent linking group that may have a (meth)acryloyl group attached, as described above.

[0217] In equation (F1), ring F 1 This indicates a divalent cyclic group. Ring F 1The "divalent cyclic group" indicated by is the same as the divalent cyclic group described above. Ring F 1 The substituent may have substituents, and examples of such substituents include halogen atoms, alkyl groups, alkoxy groups, aryl groups, arylalkyl groups, silyl groups, acyl groups, acyloxy groups, carboxyl groups, sulfo groups, cyano groups, nitro groups, hydroxyl groups, mercapto groups, oxo groups, and the like, with alkyl groups being preferred.

[0218] Commercially available resins containing a cyclic structure and a (meth)acryloyl group include "A-DOG" (a resin represented by formula (F2-1) below) manufactured by Shin-Nakamura Chemical Industry Co., Ltd.; "DCP-A" (a resin represented by formula (F2-2) below) manufactured by Kyoeisha Chemical Co., Ltd.; "NK Ester DCP" (a resin represented by formula (F2-3) below) manufactured by Shin-Nakamura Chemical Industry Co., Ltd.; and "KAYARAD R-684" and "KAYARAD R-604" manufactured by Nippon Kayaku Co., Ltd.

[0219] [ka]

[0220] Examples of resins containing a cyclic structure and amino groups include alicyclic amines and aromatic amines. While there are no particular restrictions on the number of amino groups in such resins, it is preferable that each molecule contains two or more amino groups. Furthermore, such resins may be primary, secondary, or tertiary amines. Specific examples of such resins include 4,4'-methylenebis(2,6-dimethylaniline), diphenyldiaminosulfone, 4,4'-diaminodiphenylmethane, 4,4'-diaminodiphenylsulfone, 3,3'-diaminodiphenylsulfone, m-phenylenediamine, m-xylylenediamine, 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 Examples include phenyl)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. Commercially available resins of this type include "Kayahard AA", "Kayahard AB", and "Kayahard AS" manufactured by Nippon Kayaku Co., Ltd., and "WA" manufactured by Mitsubishi Chemical Corporation.

[0221] In another preferred embodiment, (F) the thermosetting monomer comprises a benzoxazine resin. The benzoxazine resin in such embodiment may be a resin containing one or more, preferably two or more, benzoxazine rings in one molecule. A commercially available benzoxazine resin is "ALP-d" manufactured by Shikoku Chemicals, Inc.

[0222] As mentioned above, the (F) thermosetting monomer preferably contains a cyclic structure, but a compound with a structure that does not contain a cyclic structure may also be used as the (F) thermosetting monomer. The thermosetting monomer that does not contain a cyclic structure preferably contains one or more functional groups selected from the group consisting of vinyl groups, 1-propenyl groups, allyl groups, (meth)acryloyl groups, and amino groups, and more preferably contains a (meth)acryloyl group.

[0223] Examples of commercially available thermosetting monomers containing a (meth)acryloyl group and not containing a cyclic structure include "NPGDA," "FM-400," "THE-330," "PET-30," and "DPHA" manufactured by Nippon Kayaku Co., Ltd.

[0224] (F) The active group equivalent of the thermosetting monomer is preferably 50 g / eq. or more, more preferably 100 g / eq. or more, preferably 3,000 g / eq. or less, more preferably 1,000 g / eq. or less, even more preferably 500 g / eq. or less, and even more preferably 300 g / eq. or less. (F) The active group equivalent of the thermosetting monomer represents the mass of (F) thermosetting monomer per equivalent of active group. Furthermore, (v) the active group of the liquid thermosetting resin refers to a thermosetting functional group or structure, and examples include radical polymerizable groups such as vinyl groups and (meth)acryloyl groups; reactive groups other than radical polymerizable groups such as amino groups and cyanate groups; reactive cyclic structures such as benzoxazine rings; and so on.

[0225] In the resin composition according to the first embodiment, the content of (F) thermosetting monomer in the resin composition is preferably 1% by mass or more, more preferably 1.2% by mass or more, even more preferably 1.5% by mass or more, preferably 10% by mass or less, and more preferably 5% by mass or less, based on 100% by mass of the nonvolatile components in the resin composition, from the viewpoint of achieving the desired effects of the present invention.

[0226] <(G)Organic filler> In the resin composition according to the first embodiment, (G) organic filler may be included as an optional component. The (G) organic filler does not include components (A) to (F) described above. The (G) organic filler is usually immiscible with resin components other than the (G) organic filler and is included in the resin composition layer in the form of particles, and does not dissolve in the solvent and is included in the cured product while maintaining its particle state. Furthermore, one type of (G) organic filler may be used alone, or two or more types may be used in combination.

[0227] (G) As the organic filler, particles of organic material may be used. (G) As the organic material contained in the organic filler, rubber components are preferred. Examples of rubber components include silicone elastomers such as polydimethylsiloxane; olefin-based thermoplastic elastomers such as polybutadiene, polyisoprene, polychlorobutadiene, ethylene-vinyl acetate copolymer, styrene-butadiene copolymer, styrene-isoprene copolymer, styrene-isobutylene copolymer, acrylonitrile-butadiene copolymer, isoprene-isobutylene copolymer, isobutylene-butadiene copolymer, ethylene-propylene-diene terpolymer, ethylene-propylene-butene terpolymer; and thermoplastic elastomers such as acrylic-based thermoplastic elastomers such as propyl poly(meth)acrylate, butyl poly(meth)acrylate, cyclohexyl poly(meth)acrylate, and octyl poly(meth)acrylate. Furthermore, silicone-based rubbers such as polyorganosiloxane rubber may be mixed with the rubber component. The rubber component contained in the rubber particles has a glass transition temperature of, for example, 0°C or lower, preferably -10°C or lower, more preferably -20°C or lower, and even more preferably -30°C or lower.

[0228] (G) The organic filler may be a core-shell type rubber particle consisting of core particles containing the rubber components listed above and a shell portion formed by graft copolymerization of monomer components copolymerizable with the rubber components contained in the core particles. Here, "core-shell type" does not necessarily refer only to those in which the core particles and shell portion can be clearly distinguished, but also includes those in which the boundary between the core particles and shell portion is unclear, and the core particles do not have to be completely covered by the shell portion.

[0229] (G)Specific examples of organic fillers include, for example, "CHT" from Samsung SDI; "B602" from Techno UMG; "Paraloid EXL-2602", "Paraloid EXL-2603", "Paraloid EXL-2655", "Paraloid EXL-2311", "Paraloid-EXL2313", "Paraloid EXL-2315", "Paraloid KM-330", "Paraloid KM-336P", "Paraloid KCZ-201" from Dow Corporation; and "Metablen C-223A" and "Metablen E-9" from Mitsubishi Rayon Corporation. Examples include "01", "Metablen S-2001", "Metablen W-450A", "Metablen SRK-200", Kaneka Corporation's "Kaneace M-511", "Kaneace M-600", "Kaneace M-400", "Kaneace M-580", "Kaneace MR-01", and Aica Kogyo Co., Ltd.'s "Stafiloid AC3355", "Stafiloid AC3816", "Stafiloid AC3816N", "Stafiloid AC3832", "Stafiloid AC4030", and "Stafiloid AC3364".

[0230] (G) The content of the organic filler is preferably 0.1% by mass or more, more preferably 0.2% by mass or more, even more preferably 0.3% by mass or more, preferably 3% by mass or less, and more preferably 2% by mass or less, when the nonvolatile components in the resin composition layer are taken as 100% by mass.

[0231] <(H)Thermoplastic resin> The resin composition according to the first embodiment of the present invention may contain (H) thermoplastic resin as an optional component. Unless otherwise specified, the (H) thermoplastic resin does not include components (A) to (D) described above. The (H) thermoplastic resin may be compatible with resin components other than the (H) thermoplastic resin and be included in the resin composition. When the resin composition according to the first embodiment contains component (H), one type of (H) thermoplastic resin may be used alone, or two or more types may be used in combination.

[0232] (H) Examples of thermoplastic resins include polyimide resin, phenoxy resin, polystyrene resin, polyvinyl acetal resin, polyolefin resin, polybutadiene resin, polyamideimide resin, polyetherimide resin, polysulfone resin, polyethersulfone resin, polyphenylene ether resin, polycarbonate resin, polyetheretherketone resin, polyester resin, etc. Among these, (E) the thermoplastic resin preferably contains at least one of polyimide resin, phenoxy resin, and polystyrene resin.

[0233] Polyimide resins can be resins having an imide structure. Polyimide resins can generally be obtained by imidation reactions between diamine compounds and acid anhydrides, or between diisocyanate compounds and acid anhydrides. Specific examples of polyimide resins include, for example, linear polyimides obtained by reacting a bifunctional hydroxyl-terminated polybutadiene, a diisocyanate compound, and a tetrabasic acid anhydride (polyimide described in Japanese Patent Publication No. 2006-37083), and modified polyimides containing a polysiloxane skeleton (polyimides described in Japanese Patent Publication No. 2002-12667 and Japanese Patent Publication No. 2000-319386, etc.). Commercially available polyimide resins may also be used, for example, "Ricacoat SN20" and "Ricacoat PN20" manufactured by Shin Nippon Rika Co., Ltd. Polyimide resins may be used alone or in combination of two or more types.

[0234] In one preferred embodiment, the polyimide resin contains structural units represented by the following formula (H1) (hereinafter also referred to as "structural units (H1)"). The number of structural units (H1) contained in one molecule of polyimide resin is 1 or more, and is not particularly limited, but may be 100 or less, 50 or less, or 30 or less.

[0235] [ka]

[0236] (In formula (H1), R H1 This represents a tetravalent group represented by the following formula (H2-1), R H2 This represents a divalent group represented by the following formula (H2-2).

[0237] [ka]

[0238] (In formula (H2-1), Ar H11 Ar H12 Ar H13 and Ar H14 Each of these independently represents an aromatic ring which may have substituents, L H11 , L H12 and L H13 Each of these independently represents a divalent linking group. n H1 This represents an integer of 0 or 1 or greater, The wavy line indicates a connection point.

[0239] [ka]

[0240] (In formula (H2-2), Ar H21 Ar H22 Ar H23 and Ar H24Each of these independently represents an aromatic ring which may have substituents, L H21 , L H22 and L E23 Each of these independently represents a divalent linking group. n H2 This represents an integer greater than or equal to 1, The wavy line indicates a connection point.

[0241] In equation (H2-1), Ar H11 Ar H12 Ar H13 and Ar H14 Each of these independently represents an aromatic ring that may or may not have substituents. H11 Ar H12 Ar H13 and Ar H14 The aromatic ring represented by (hereinafter also referred to as "aromatic ring F") is preferably an aromatic ring having 6 to 100 carbon atoms, more preferably 6 to 50 carbon atoms, and even more preferably an aromatic carbon ring having 6 to 100 carbon atoms, and even more preferably 6 to 50 carbon atoms.

[0242] Ar H11 Ar H12 Ar H13 and Ar H14 Examples of aromatic rings represented by Ar include monocyclic aromatic rings such as benzene rings, furan rings, thiophene rings, pyrrole rings, pyrazole rings, oxazole rings, isoxazole rings, thiazole rings, imidazole rings, pyridine rings, pyridazine rings, pyrimidine rings, and pyrazine rings; condensed rings formed by the fusion of two or more monocyclic aromatic rings such as naphthalene rings, anthracene rings, benzofuran rings, isobenzofuran rings, indole rings, isoindole rings, benzothiophene rings, benzimidazole rings, indazole rings, benzoxazole rings, benzoisoxazole rings, benzothiazole rings, quinoline rings, isoquinoline rings, quinoxaline rings, acridine rings, quinazoline rings, sinnoline rings, and phthalazine rings; and condensed rings formed by the fusion of one or more monocyclic aromatic rings with one or more monocyclic non-aromatic rings, such as indan rings, fluorene rings, and tetraline rings. H11 Ar H12 Ar H13 and ArH14 The aromatic rings represented are preferably, independently, aromatic carbon rings having 6 to 14 carbon atoms, which may have substituents, and more preferably, benzene rings.

[0243] In equation (H2-1), Ar H11 Ar H12 Ar H13 and Ar H14 When represents an aromatic ring having substituents, the number of substituents is not limited. Examples of such substituents (hereinafter also referred to as "substituents S") include, independently of each other, halogen atoms, alkyl groups, cycloalkyl groups, alkoxy groups, cycloalkyloxy groups, aryl groups, aryloxy groups, arylalkyl groups, arylalkoxy groups, monovalent heterocyclic groups, alkylidene groups, amino groups, silyl groups, acyl groups, acyloxy groups, carboxyl groups, sulfo groups, cyano groups, nitro groups, hydroxyl groups, mercapto groups, and oxo groups.

[0244] In equation (H2-1), L H11 , L H12 and L H13 Each of these independently represents a divalent linking group. H11 , L H12 and L H13 The divalent linking group represented by is preferably a divalent group consisting of one or more skeletal atoms selected from carbon atoms, oxygen atoms, nitrogen atoms, sulfur atoms, and silicon atoms (for example, 1 to 3000, 1 to 1000, 1 to 100, and 1 to 50 atoms). Examples of divalent linking groups include -SO2-, -CO-, -COO-, -O-, -S-, -O-C6H4-O- (where -C6H4- represents a phenylene group), -O-C6H4-C(CH3)2-C6H4-O-, and -COO-(CH2). m -OCO- (where m represents an integer from 1 to 20), -COO-H2C-HC(-OC(=O)-CH3)-CH2-OCO-, alkylene group, alkenylene group, alkynylene group, arylene group, heteroarylene group, -C(=O)-, -C(=O)-O-, -NR 0 -(Here, R 0) represents a hydrogen atom and an alkyl group having 1 to 3 carbon atoms. ) and -C(=O)-NR 0 - are listed.

[0245] L H11 , L H12 and L H13 The number of carbon atoms in the alkylene group is preferably 1 to 10, more preferably 1 to 6, and even more preferably 1 to 5 or 1 to 4. H11 , L H12 and L H13 The number of carbon atoms in the alkenylene group is preferably 2 to 10, more preferably 2 to 6, and even more preferably 2 to 5. H11 , L H12 and L H13 The number of carbon atoms in the arylene group is preferably 6 to 20, more preferably 6 to 10. H11 , L H12 and L H13 The number of carbon atoms in the heteroarylene group is preferably 2 to 20, more preferably 3 to 10, 4 to 10, or 5 to 10.

[0246] L H11 , L H12 and L H13 The divalent linking group represented by preferably does not contain an aromatic ring. In one embodiment, L H11 The divalent linking group represented by and L H13 The divalent linking groups represented by are the same as L H11 The divalent linking group represented by and L E12 The divalent linking groups represented by are different from each other. In one preferred embodiment, L H11 and L H13 is -O-, L H12 is an alkylene group which may have substituents. In a more preferred embodiment, L H11 and L H13 is -O-, L H12 This is a dimethylmethylene group.

[0247] In equation (H2-1), n H1 n represents an integer of 0 or 1 or greater. In a preferred embodiment, n E1n represents an integer greater than or equal to 1. H1 The upper limit of the integer represented by is not particularly restricted, but it could be, for example, 50, 40, 30, or 20.

[0248] In the tetravalent group represented by formula (H2-1), L H11 and L H13 is -O- and L H12 It is preferable that is an alkylene group which may have substituents. Also, Ar H11 Ar H12 Ar H13 and Ar H14 However, each is independently an aromatic carbon ring having 6 to 14 carbon atoms, which may have substituents, L H11 and L H13 is -O- and L H12 It is more preferable that is an alkylene group which may have substituents. Also, Ar H11 Ar H12 Ar H13 and Ar H14 However, each is independently an aromatic carbon ring having 6 to 14 carbon atoms, which may have substituents, L H11 and L H13 is -O- and L H12 It is even more preferable that the group is a dimethylmethylene group.

[0249] In equation (H2-2), Ar H21 Ar H22 Ar H23 and Ar E24 Each of these independently represents an aromatic ring that may or may not have substituents. H21 Ar H22 Ar H23 and Ar H24 Examples of the aromatic ring represented by and the substituents that the aromatic ring may have are the same as those described above for the aromatic ring F and substituent S. Therefore, in one preferred embodiment, Ar H21 Ar H22 Ar H23 and Ar H24 Each of these is independently an aromatic carbon ring having 6 to 14 carbon atoms, which may have substituents.

[0250] In equation (H2-2), L H21 , L H22 and L H23 Each of these independently represents a divalent linking group. H21 , L H22 and L H23 An example of a divalent linking group represented by is L H11 , L H12 and L H13 This is similar to the divalent linking group represented by . Therefore, in a preferred embodiment, L H21 and L H23 is -O-, L H22 is an alkylene group which may have substituents, and in a more preferred embodiment, L H21 and L H23 is -O-, L H22 This is a dimethylmethylene group.

[0251] In equation (H2-2), n H2 n represents an integer greater than or equal to 1. In one preferred embodiment, n H2 n represents an integer greater than or equal to 2. H2 The upper limit of the integer represented by is not particularly restricted, but it could be, for example, 60, 50, 40, or 30.

[0252] In the divalent group represented by formula (H2-2), L H21 and L H23 is -O- and L H22 It is preferable that is an alkylene group which may have substituents. Also, Ar H21 Ar H22 Ar H23 and Ar H24 However, each is independently an aromatic carbon ring having 6 to 14 carbon atoms, which may have substituents, L H21 and L H23 is -O- and L H22 It is more preferable that is an alkylene group which may have substituents. Also, Ar H21 Ar H22 Ar H23 and Ar H24However, each is independently an aromatic carbon ring having 6 to 14 carbon atoms, which may have substituents, L H21 and L H23 is -O- and L H22 It is even more preferable that the group is a dimethylmethylene group.

[0253] In the tetravalent group represented by formula (H2-1) and the divalent group represented by formula (H2-2), Ar H11 Ar H12 Ar H13 and Ar H14 However, each is independently an aromatic carbon ring having 6 to 14 carbon atoms, which may have substituents, and Ar H21 Ar H22 Ar H23 and Ar H24 However, each is preferably an aromatic carbon ring having 6 to 14 carbon atoms, which may have substituents. H11 and L H13 is -O-, L H12 L is an alkylene group which may have substituents. H21 and L H23 is -O- and L H22 It is preferable that the alkylene group may have substituents.

[0254] The above structural unit (H1) can be obtained, for example, by known methods for producing polyimide resins, typically by polymerizing a monomer composition containing a tetracarboxylic dianhydride and a diamine compound to imidize it, or by polymerizing a monomer composition containing a tetracarboxylic dianhydride and a diisocyanate compound to imidize it. It is permissible for the polyimide resin to partially contain polyamic acid structures that may be formed during the imidization process.

[0255] The structural unit (H1) may be obtained, for example, by reacting 2,2-bis[4-(3,4-dicarboxyphenoxy)phenyl]propane dianhydride (a compound represented by the following formula (H3-1); hereinafter also referred to as "BPADA") with 4,4'-[1,4-phenylenebis[(1-methylethylidene)-4,1-phenyleneoxy]]bisbenzeneamine (a compound represented by the following formula (H3-2); hereinafter also referred to as "BPPAN"). That is, in one embodiment, R in the structural unit (H1) H1 It is a skeleton derived from BPADA, and R H2 This is a skeleton derived from BPPAN.

[0256] [ka]

[0257] Furthermore, the polyimide resin may also contain structural units represented by the following formula (H4) (hereinafter also referred to as "structural units (H4)"). Therefore, in one embodiment, the polyimide resin further contains structural units represented by the following formula (H4). The number of structural units (H4) contained per molecule of polyimide resin is 0 or 1 or more, and is not particularly limited, but may be 100 or less, 50 or less, or 30 or less.

[0258] [ka]

[0259] (In formula (H4), R H3 This represents a tetravalent aliphatic group which may have a substituent or a tetravalent aromatic group which may have a substituent; R H4 R represents a divalent aliphatic group which may have substituents or a divalent aromatic group which may have substituents. However, R H3 R H1 In the same case, R H4 is R H2 Unlike R H4 R H2 In the same case, RH3 is R H1 (This is different.)

[0260] In equation (H4), R H3 This represents a tetravalent aliphatic group that may have substituents or a tetravalent aromatic group that may have substituents.

[0261] R H3 The tetravalent aliphatic group represented by is a tetravalent group comprising at least carbon atoms, and preferably consisting of one or more skeletal atoms selected from carbon atoms, oxygen atoms, nitrogen atoms, sulfur atoms, and silicon atoms (e.g., 1 to 3000, 1 to 1000, 1 to 100, 1 to 50). H3 The tetravalent aliphatic group represented by R3 is more preferably a tetravalent aliphatic group having 1 to 100 carbon atoms, and even more preferably 1 to 50 carbon atoms. In formula (H4), R H3 When represents a tetravalent aliphatic group having a substituent, the examples of the substituent are the same as the examples of substituent S.

[0262] R H3 The tetravalent aromatic group represented by is preferably a tetravalent aromatic group having 6 to 100 carbon atoms, more preferably 6 to 50 carbon atoms. The aromatic group contains at least an aromatic ring. An example of an aromatic ring included in an aromatic group is Ar in formula (H2-1). H11 Ar H12 Ar H13 and Ar H14 This is the same as the example of an aromatic ring represented by . In equation (H4), R H3 When represents a tetravalent aromatic group having a substituent, the examples of the substituent are the same as the examples of substituent S.

[0263] R H3The tetravalent aromatic group represented by can be a group obtained by removing two acid anhydride groups from a tetracarboxylic dianhydride having an aromatic group that may have substituents. Specific examples of tetracarboxylic dianhydrides having an aromatic group that may have substituents include BPADA, pyromellitic dianhydride, 3,3',4,4'-biphenyltetracarboxylic dianhydride, 4,4'-oxydiphthalic anhydride, 3,3',4,4'-benzophenonetetracarboxylic dianhydride, and 3,3',4,4'-diphenylsulfonetetracarboxylic dianhydride.

[0264] In equation (H4), R H4 This represents a divalent aliphatic group or a divalent aromatic group that may have substituents.

[0265] R H4 The divalent aliphatic group represented by is a divalent group comprising at least carbon atoms, and preferably consisting of one or more skeletal atoms selected from carbon atoms, oxygen atoms, nitrogen atoms, sulfur atoms, and silicon atoms (e.g., 1 to 3000, 1 to 1000, 1 to 100, 1 to 50). In formula (H4), R H4 The divalent aliphatic group represented by is more preferably a divalent aliphatic group having 1 to 100 carbon atoms, and even more preferably 1 to 50 carbon atoms.

[0266] In equation (H4), R H4 When R represents a divalent aliphatic group having a substituent, the examples of the substituent are the same as the examples of substituent S, for example, an alkyl group having 1 to 6 carbon atoms. Therefore, in one embodiment, R H4 is a divalent aliphatic group which may have substituents, and one of the substituents is an alkyl group having 1 to 6 carbon atoms. In one embodiment, R H4 However, it is a divalent aliphatic group which may have substituents, and is a divalent group obtained by removing two amino groups from isophoronediamine.

[0267] R H4When represents a divalent aliphatic group which may have substituents, it may be a group obtained by removing two amino groups from a diamine compound having a linear aliphatic group which may have substituents, selected from 1,2-diaminoethane, 1,3-diaminopropane, 1,4-diaminobutane, 1,5-diaminopentane, 1,6-hexanediamine, 1,7-heptanediamine, 1,8-octanediamine, 1,9-nonanediamine, 1,10-decanediamine, 1,11-undecanediamine, and 1,12-dodecanediamine.

[0268] R H4 When represents a divalent aliphatic group which may have substituents, it may be a group obtained by removing two amino groups from a diamine compound having a branched aliphatic group which may have substituents, selected from 1,2-diaminopropane, 1,2-diamino-2-methylpropane, 1,3-diamino-2-methylpropane, 1,3-diamino-2,2-dimethylpropane, 1,3-diaminopentane, and 1,5-diamino-2-methylpentane.

[0269] R H4 When represents a divalent aliphatic group which may have substituents, 5-amino-1,3,3-trimethylcyclohexanemethylamine (isophorone diamine), 1,4-diaminocyclohexane, 1,3-diaminocyclohexane, 1,4-cyclohexanebis(methylamine), 1,3-cyclohexanebis(methylamine), 4,4'-diaminodicyclohexylmethane, bis(4-amino-3-methylcyclohexyl)methane, 3(4),8(9)-bis(aminomethyl)tricyclo[5.2.1.0 2,6 The group may be a diamine compound having an aliphatic group which may have substituents, selected from decane, 2,5(6)-bis(aminomethyl)bicyclo[2.2.1]heptane, 1,3-diaminoadamantane, 3,3'-diamino-1,1'-biadamantyl, and 1,6-diaminoadamantane, from which two amino groups have been removed. These diamine compounds are characterized in that their aliphatic group contains an alicyclic carbocyclic ring.

[0270] R H4The divalent aromatic group represented by is preferably a divalent aromatic group having 6 to 100 carbon atoms, more preferably 6 to 50 carbon atoms. The aromatic group includes at least an aromatic ring. Examples of aromatic rings included in the aromatic group are the same as examples of aromatic ring E. In formula (H4), R H4 When represents a divalent aromatic group having a substituent, the examples of the substituent are the same as the examples of substituent S.

[0271] R H4 However, when representing a divalent aromatic group which may have substituents, it may be a group obtained by removing two amino groups from a diamine compound having an aromatic group which may have substituents, selected from 4,4'-diaminodiphenyl ether, 1,4-phenylenediamine, and 2,2-bis[4-(4-aminophenoxy)phenyl]propane.

[0272] However, R H3 R H1 In the same case, R H4 is R H2 Unlike R H4 R H2 In the same case, R H3 is R H1 It is different. In one embodiment, R H3 is R H1 It is the same as this.

[0273] The structural unit (H4) described above can be obtained, for example, by a known method for producing polyimide resins. The structural unit (H4) can be obtained, for example, by reacting BPADA with isophorone diamine. That is, the R in such structural unit (H4) H3 In one embodiment, this is a skeleton derived from BPADA, and R H4 This is a skeleton derived from isophorone diamine. H3 R H1 If it is the same as R H3 and R H1 In one embodiment, this is a skeleton derived from BPADA.

[0274] The terminal structure of the polyimide resin is not particularly limited. For example, the terminal structure of the polyimide resin may be an acid anhydride group, a carboxyl group, or an amino group derived from its raw material compound (e.g., an acid such as BPADA, or an amine compound such as BPPAN).

[0275] The glass transition temperature Tg (°C) of polyimide resin is preferably 140°C or higher, more preferably 145°C or higher, and even more preferably 150°C or higher, 160°C or higher, or 170°C or higher. There is no particular upper limit, but it can be 300°C or lower. The glass transition temperature Tg (°C) of polyimide resin can be measured by thermomechanical analysis (TMA).

[0276] The content of structural units (H1) in the polyimide resin is preferably 5% by mass or more, more preferably 10% by mass or more, and even more preferably 20% by mass or more, 30% by mass or more, or 40% by mass or more. The upper limit of this content can be, for example, 98% by mass or less, 95% by mass or less, 90% by mass or less, or 85% by mass or less. Here, the content of structural units (H1) (mass percentage) can be calculated from the proportion of the amount (parts by mass) of each material used in the synthesis of the polyimide resin. Alternatively, the molecular weight of the polyimide resin and the formula weight of the structural units (H1) may be specified, and the content of structural units (H1) may be calculated as the ratio of the formula weight of structural units (H1) to the molecular weight. When the polyimide resin is a polymer, it is preferable that the content of structural units (H1) estimated from the degree of polymerization falls within the above range.

[0277] The content of structural units (H4) in the polyimide resin may be 0% by mass (i.e., no structural units (H4) are included), and there is no upper limit as long as it does not hinder the effects of the present invention. If the polyimide resin further contains structural units (H4), the content of structural units (H4) in the polyimide resin may be, for example, 1% by mass or more, 5% by mass or more, 10% by mass or more, 20% by mass or more, or 30% by mass or more, 95% by mass or less, 90% by mass or less, 80% by mass or less, 70% by mass or less, or 60% by mass or less. Here, the content of structural units (H4) is calculated in the same way as the content of structural units (H1).

[0278] The weight-average molecular weight (Mw) of the polyimide resin is preferably 1,000 or more, preferably 200,000 or less, more preferably 150,000 or less or 100,000 or less, even more preferably 80,000 or less or 60,000 or less, and even more preferably 40,000 or less or 30,000 or less. In one embodiment, the upper limit of the weight-average molecular weight (Mw) of the polyimide resin may be 5,000 or less or 3,000 or less. The weight-average molecular weight of the polyimide resin is the weight-average molecular weight in terms of polystyrene, measured by gel permeation chromatography (GPC).

[0279] Examples of phenoxy resins include phenoxy resins having one or more skeletons selected from the group consisting of bisphenol A skeleton, bisphenol F skeleton, bisphenol S skeleton, bisphenolacetophenone skeleton, novolac skeleton, biphenyl skeleton, fluorene skeleton, dicyclopentadiene skeleton, norbornene skeleton, naphthalene skeleton, anthracene skeleton, adamantane skeleton, terpene skeleton, and trimethylcyclohexane skeleton. The terminal end of the phenoxy resin may be any functional group such as a phenolic hydroxyl group or an epoxy group. Specific examples of phenoxy resins include "1256" and "4250" (both phenoxy resins containing a bisphenol A skeleton) manufactured by Mitsubishi Chemical Corporation; "YX8100" (phenoxy resin containing a bisphenol S skeleton) manufactured by Mitsubishi Chemical Corporation; "YX6954" (phenoxy resin containing a bisphenol acetophenone skeleton) manufactured by Mitsubishi Chemical Corporation; "FX280" and "FX293" manufactured by Nippon Steel Chemical & Material Co., Ltd.; and "YL7500BH30", "YX6954BH30", "YX7553", "YX7553BH30", "YL7769BH30", "YL6794", "YL7213", "YL7290", "YL7482", "YL7891BH30", and "YX7891T30" manufactured by Mitsubishi Chemical Corporation. Phenoxy resins may be used individually or in combination of two or more types.

[0280] Specific examples of polystyrene resins include Asahi Kasei's "H1041," "ToughTec H1043," "ToughTec P2000," and "ToughTec MP10" (hydrogenated styrene thermoplastic elastomers), "ToughTec N503M" (modified styrene elastomer containing carboxyl groups), "ToughTec N501" (modified styrene elastomer containing amino groups), and "ToughTec M1913" (modified styrene elastomer containing acid anhydride groups); Daicel's "Epofriend AT501" and "CT310" (epoxidized styrene-butadiene thermoplastic elastomers); and Kuraray's "Septon HG252" (modified styrene elastomer containing hydroxyl groups) and "Septon S8104" (unmodified styrene elastomer). Polystyrene resins may be used individually or in combination of two or more types.

[0281] 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 S-Rec BH series, BX series (e.g., BX-5Z), KS series (e.g., KS-1), BL series, BM series, etc., manufactured by Sekisui Chemical Co., Ltd. Polyvinyl acetal resins may be used individually or in combination of two or more types.

[0282] Examples of polyolefin resins include ethylene-based copolymer resins such as low-density polyethylene, ultra-low-density polyethylene, high-density polyethylene, ethylene-vinyl acetate copolymer, ethylene-ethyl acrylate copolymer, and ethylene-methyl acrylate copolymer; and polyolefin polymers such as polypropylene and ethylene-propylene block copolymer. Polyolefin resins may be used individually or in combination of two or more types.

[0283] Examples of polybutadiene resins include hydrogenated polybutadiene backbone-containing resins, hydroxyl group-containing polybutadiene resins, phenolic hydroxyl group-containing polybutadiene resins, carboxyl group-containing polybutadiene resins, acid anhydride group-containing polybutadiene resins, epoxy group-containing polybutadiene resins, isocyanate group-containing polybutadiene resins, urethane group-containing polybutadiene resins, polyphenylene ether resins, and polybutadiene resins. Polybutadiene resins may be used individually or in combination of two or more types.

[0284] Specific examples of polyamide-imide resins include "Viromax HR11NN" and "Viromax HR16NN" manufactured by Toyobo Co., Ltd. Other specific examples of polyamide-imide resins include modified polyamide-imides such as "KS9100" and "KS9300" (polysiloxane skeleton-containing polyamide-imide) manufactured by Resonaq Corporation. Polyamide-imide resins may be used individually or in combination of two or more types.

[0285] Specific examples of polysulfone resins include Solvay Advanced Polymers' polysulfones "P1700" and "P3500." Polysulfone resins may be used individually or in combination of two or more types.

[0286] Specific examples of polyethersulfone resins include "PES5003P" manufactured by Sumitomo Chemical Co., Ltd. Specific examples of polyphenylene ether resins include "NORYL SA90" manufactured by SABIC Corporation. Specific examples of polyetherimide resins include "Ultem" manufactured by GE Corporation.

[0287] Examples of polycarbonate resins include hydroxyl group-containing carbonate resins, phenolic hydroxyl group-containing carbonate resins, carboxyl group-containing carbonate resins, acid anhydride group-containing carbonate resins, isocyanate group-containing carbonate resins, and urethane group-containing carbonate resins. Specific examples of polycarbonate resins include "FPC0220" from Mitsubishi Gas Chemical Co., Ltd., "T6002" and "T6001" (polycarbonate diols) from Asahi Kasei Corporation, and "C-1090," "C-2090," and "C-3090" (polycarbonate diols) from Kuraray Co., Ltd. Polycarbonate resins may be used individually or in combination of two or more types.

[0288] Specific examples of polyetherketone resins include "Sumiproi K" manufactured by Sumitomo Chemical Co., Ltd.

[0289] Examples of polyester resins include polyethylene terephthalate resin, polyethylene naphthalate resin, polybutylene terephthalate resin, polybutylene naphthalate resin, polytrimethylene terephthalate resin, polytrimethylene naphthalate resin, and polycyclohexanedimethyl terephthalate resin. Polyester resins may be used individually or in combination of two or more types.

[0290] If the resin composition according to the first embodiment contains a thermoplastic resin other than polyimide resin, the weight-average molecular weight (Mw) of the thermoplastic resin other than polyimide resin is preferably 5,000 or more, more preferably 8,000 or more, even more preferably 10,000 or more, 15,000 or more, or 20,000 or more, preferably 200,000 or less, more preferably 150,000 or less, or 100,000 or less, and even more preferably 80,000 or less, or 60,000 or less. The weight-average molecular weight of the thermoplastic resin other than polyimide resin is the weight-average molecular weight in terms of polystyrene, measured by gel permeation chromatography (GPC).

[0291] When the resin composition according to the first embodiment contains a thermoplastic resin (H), the content of component (H) in the resin composition is, for example, 0.01% by mass or more, preferably 0.05% by mass or more, more preferably 0.1% by mass or more, even more preferably 0.2% by mass or more, preferably 5% by mass or less, more preferably 3% by mass or less, and even more preferably 2% by mass or less, based on 100% by mass of the nonvolatile components in the resin composition.

[0292] <(I) Other additives> The resin composition according to the first embodiment of the present invention may further contain, in combination with the components (A) to (H) described above, (I) other additives as optional components. The (I) other additives do not include those corresponding to the components (A) to (H) described above.

[0293] (I) Other additives include, for example, epoxy resins; organometallic compounds such as organocopper compounds and organozinc compounds; colorants such as phthalocyanine blue, phthalocyanine green, iodine green, diazo yellow, crystal violet, titanium dioxide, and carbon black; leveling agents such as silicone-based leveling agents and acrylic polymer-based leveling agents; thickeners such as bentonite and montmorillonite; defoaming agents such as silicone-based defoaming agents, acrylic-based defoaming agents, fluorine-based defoaming agents, and vinyl resin-based defoaming agents; and benzotriazole-based ultraviolet light. Examples of additives include UV absorbers such as absorbents; adhesion improvers such as urea silane; antioxidants such as hindered phenol antioxidants; fluorescent whitening agents such as stilbene derivatives; surfactants such as fluorine-based surfactants and silicone-based surfactants; flame retardants such as nitrogen-based flame retardants (e.g., melamine sulfate), halogen-based flame retardants, and inorganic flame retardants (e.g., antimony trioxide); and stabilizers such as borate-based stabilizers, titanate-based stabilizers, aluminate-based stabilizers, zirconate-based stabilizers, isocyanate-based stabilizers, carboxylic acid-based stabilizers, and carboxylic acid anhydride-based stabilizers. (I) Other additives may be used individually or in combination of two or more types. When the resin composition according to the first embodiment contains (I) other additives, the content of component (I) in the resin composition may be determined according to the properties required for the resin composition. Furthermore, the components (A) to (H) described above may have functions such as organic fillers, organometallic compounds, colorants, polymerization inhibitors, leveling agents, thickeners, defoamers, ultraviolet absorbers, adhesion enhancers, adhesion-improving agents, antioxidants, fluorescent whitening agents, surfactants, flame retardants, dispersants, and stabilizers. In that case, such components shall be considered as components (A) to (H) described above, rather than as component (I).

[0294] <(J) Organic Solvents> The resin composition according to the first embodiment of the present invention may further contain an organic solvent (J) as an optional volatile component in combination with the non-volatile components such as components (A) to (I) described above. Examples of organic solvents include ketone solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone; ester solvents such as methyl acetate, ethyl acetate, butyl acetate, isobutyl acetate, isoamyl acetate, methyl propionate, ethyl propionate, and γ-butyrolactone; ether solvents such as tetrahydropyran, tetrahydrofuran, 1,4-dioxane, diethyl ether, diisopropyl ether, dibutyl ether, diphenyl ether, and anisole; alcohol solvents such as methanol, ethanol, propanol, butanol, and ethylene glycol; and 2-ethoxyethyl acetate, propylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, ethyl diglycol acetate, γ-butyrolactone, and methoxypropionate. Examples include ether ester solvents such as tyl; ester alcohol solvents such as methyl lactate, ethyl lactate, and methyl 2-hydroxyisobutyrate; ether alcohol solvents such as 2-methoxypropanol, 2-methoxyethanol, 2-ethoxyethanol, propylene glycol monomethyl ether, and diethylene glycol monobutyl ether (butyl carbitol); amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methyl-2-pyrrolidone; sulfoxide solvents such as dimethyl sulfoxide; nitrile solvents such as acetonitrile and propionitrile; aliphatic hydrocarbon solvents such as hexane, cyclopentane, cyclohexane, and methylcyclohexane; and aromatic hydrocarbon solvents such as benzene, toluene, xylene, ethylbenzene, and trimethylbenzene. (J) Organic solvents may be used individually or in combination of two or more types.

[0295] If the resin composition according to the first embodiment contains (J) an organic solvent, the content of component (J) in the resin composition may be, for example, 60% by mass or less, 40% by mass or less, 30% by mass or less, 25% by mass or less, or 20% by mass or less, based on 100% by mass of all components of the resin composition. Alternatively, the content of organic solvent (J) in the resin composition may be 0% by mass.

[0296] [Resin composition according to the second embodiment] The resin composition according to the second embodiment of the present invention includes (A) a TEMPO-based compound, (B) an inorganic filler, (C) a maleimide resin, and (D-2) a vinyl resin containing a specific structural unit represented by formula (D2-1) and a specific end group, thereby providing a resin composition in which the dielectric loss tangent is reduced, the crack resistance in desmear treatment is good, and plating penetration is suppressed.

[0297] The resin composition according to the second embodiment may contain any additional components in combination with components (A), (B), (C), and (D-2). Examples of optional components include (E) curing accelerators, (F) thermosetting monomers, (G) organic fillers, (H) thermoplastic resins, (I) other additives, and (J) organic solvents. The components included in the resin composition according to the second embodiment will be described in detail below.

[0298] The components (A) to (C) and (E) to (J) included in the resin composition according to the second embodiment may be the same as the components (A) to (C) and (E) to (J) included in the resin composition according to the first embodiment. The range of content of components (A) to (C) and (E) to (J) in the second embodiment may be the same as the range of content described for the resin composition according to the first embodiment. Each of the components (A) to (C) and (E) to (J) may be used individually or in combination of two or more types.

[0299] Note that (B) Maleimide resin does not include components corresponding to (D-2) described later. (E) Curing accelerator does not include components (A) to (D-2) and components (F) to (H) mentioned above unless otherwise specified. (H) Thermoplastic resin does not include components (A) to (G) unless otherwise specified.

[0300] <(D-2) Compounds containing a second specific structural unit and a specific terminal group> The resin composition according to the second embodiment of the present invention includes a compound containing a structural unit represented by the following formula (D2-1) and an end group represented by the following formula (y) as component (D-2) (a compound containing a second specific structural unit and a specific end group). Hereinafter, the structural unit represented by formula (D2-1) may be referred to as the "second specific structural unit" or "structural unit (2)". Component (D-2) may be used alone or in combination of two or more types.

[0301] [ka]

[0302] (In formula (D2-1), R 21 Each of these independently represents a divalent nitrogen-containing heteroaromatic group which may have substituents, R 22 Each of these independently represents a divalent aromatic hydrocarbon group which may have substituents, R 23 This represents a hydrocarbon group having 1 to 20 carbon atoms, to which one or more groups represented by the following formula (d1) are bonded. X 2 These are, independently, -O-, -S-, or -N(R 24 )- represents, R 24 (This represents a hydrogen atom, a monovalent hydrocarbon group having 1 to 20 carbon atoms, a monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms, or a group in which the hydrocarbon group or a portion of the halogenated hydrocarbon group is substituted with at least one atom selected from oxygen and sulfur atoms.)

[0303] [ka]

[0304] (In formula (d1), * indicates a bonding site with a hydrocarbon group having 1 to 20 carbon atoms. ** indicates the binding site with other structural units contained in component (D-2), R 22 and X 2 These are, respectively, R in the above formula (D2-1). 22 and X 2 It is similar to this.

[0305] [ka]

[0306] (In formula (y), Y represents a monovalent organic group with 3 to 50 carbon atoms that contains a radical polymerizable group other than a maleimide group. The wavy line indicates a connection point.

[0307] In equation (D2-1), R 21 Each of these independently represents a divalent nitrogen-containing heteroaromatic group which may have substituents. 21 An example of a "divalent nitrogen-containing heteroaromatic group which may have substituents" represented by is R in formula (D1-1). 1 This is equivalent to the "divalent nitrogen-containing heteroaromatic group which may have substituents" represented by . Therefore, R 21 It is preferable that this is a divalent group consisting of a pyrimidine ring which may have substituents.

[0308] R 21 The substituents that the group represented by can have include, for example, R in formula (D1-1). 1 This is similar to the substituents that the group represented by can have.

[0309] R 21The substituents that the group represented by may have are, from the viewpoint of excellent polymerization reactivity in the synthesis of component (D-1), preferably a halogen atom, a hydrocarbon group having 1 to 6 carbon atoms, a halogenated hydrocarbon group having 1 to 6 carbon atoms, a nitro group, a cyano group, an amino group, or a salt of an amine, more preferably a fluorine atom, a chlorine atom, a methyl group, a tert-butyl group, a phenyl group, a nitro group, a cyano group, or a primary amino group, and even more preferably a phenyl group.

[0310] In particular, from the viewpoint of achieving the desired effects of the present invention, R 21 The group represented by is preferably without substituents or has a phenyl group as a substituent, and more preferably has a phenyl group as a substituent.

[0311] R 21 Two binding sites (X) in the group represented by 2 The position of the binding site (which binds to etc.) is not particularly limited, but the meta position is preferred from the viewpoint of excellent polymerization reactivity in the synthesis of component (D-2). 21 If is a divalent group consisting of a pyrimidine ring which may have substituents, for example, it is preferable to have a bonding site at the 4th and 6th carbons of the pyrimidine ring. Also, in such a case, R 21 In the group represented by , it is preferable that the substituent is located at the carbon atom at position 2 of the pyrimidine ring.

[0312] In equations (D2-1) and (d1), R 22 Each of these independently represents a divalent aromatic hydrocarbon group which may have substituents. A specific example of a divalent aromatic hydrocarbon group is the arylene group. Examples of arylene groups include phenylene, naphthylene, anthrylene, and biphenylene (-C6H4-C6H4-).

[0313] R 22 The substituents that the group represented by can have include, for example, R in formula (D1-1). 1 This is similar to the substituents that the group represented by can have.

[0314] R 22 The groups represented by preferably have a structure that is independently represented by the following formula (D2-2).

[0315] [ka]

[0316] (In formula (D2-2), * represents R in the above formula (D2-1). 23 This represents the bonding site with a hydrocarbon group having 1 to 20 carbon atoms, and in formula (d1), it represents the bonding site with a hydrocarbon group having 1 to 20 carbon atoms; *** is X in formula (D2-1) or formula (d1) above. 2 This represents the connection site; R 25 This represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or a cycloalkyl group having 3 to 10 carbon atoms; n D1 This represents an integer between 0 and 2; n D2 (This represents an integer between 0 and 4.)

[0317] In equation (D2-2), R 25 This represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or a cycloalkyl group having 3 to 10 carbon atoms.

[0318] R 25 Examples of alkyl groups having 1 to 10 carbon atoms include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, and n-pentyl groups.

[0319] R 25 Examples of alkoxy groups having 1 to 10 carbon atoms in this context include methoxy, ethoxy, n-propoxy, isopropoxy, butoxy, pentoxy, hexoxy, heptoxy, and octoxy groups.

[0320] R 25 Examples of cycloalkyl groups having 3 to 10 carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl groups.

[0321] In equation (D2-2), n D1 This represents an integer between 0 and 2, preferably 0 or 1.

[0322] In equation (D2-2), n D2 This represents an integer between 0 and 4, preferably between 1 and 3.

[0323] The structure represented by formula (D2-2) is preferably the same as formula (D2-3-1) or formula (D2-3-2).

[0324] [ka]

[0325] (In formulas (D2-3-1) and (D2-3-2), R 26 Each of these independently represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or a cycloalkyl group having 3 to 10 carbon atoms; n D3 This represents an integer between 0 and 3; n D4 This represents an integer between 0 and 2; *, ***, R 25 , and n D1 These correspond to *, ***, and R in the above formula (D2-2), respectively. 25 and n D1 It is similar to this.

[0326] In equations (D2-3-1) and (D2-3-2), R 26 Each of these independently represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or a cycloalkyl group having 3 to 10 carbon atoms. 26An example of the "alkyl group having 1 to 10 carbon atoms, alkoxy group having 1 to 10 carbon atoms, or cycloalkyl group having 3 to 10 carbon atoms" represented by is R in formula (D2-2). 25 This is equivalent to the "alkyl group having 1 to 10 carbon atoms, alkoxy group having 1 to 10 carbon atoms, or cycloalkyl group having 3 to 10 carbon atoms" represented by [the symbol].

[0327] In equation (D2-3-1), n D3 This represents an integer between 0 and 3, preferably between 0 and 2.

[0328] In equation (D2-3-2), n D4 This represents an integer between 0 and 2, preferably 0 or 1.

[0329] In equation (D2-1), R 23 R represents a hydrocarbon group having 1 to 20 carbon atoms to which one or more groups represented by formula (d1) are bonded, 23 The structure of the "hydrocarbon group having 1 to 20 carbon atoms" in this context is not particularly limited and may be any of the following: a structure consisting of an aliphatic group, a structure consisting of an aromatic group, or a structure consisting of a combination of an aliphatic group and an aromatic group. Furthermore, the aliphatic group may be a linear hydrocarbon group, a cyclic hydrocarbon group (i.e., an alicyclic hydrocarbon group), or a combination thereof. In addition, the linear hydrocarbon group may be either linear or branched.

[0330] R 23 In the group represented by formula (d1), if the part remaining after removing the group represented by formula (d1) is D, then in the structural unit represented by formula (D2-1), -R 22 -R 23 -R 22 The substructure represented by - can be expressed by the following formula (D2-4). That is, the structural unit represented by formula (D2-1) has a branched structure.

[0331] [ka]

[0332] (In formula (D2-4), D is R in equation (D2-1) 23 This represents the part obtained by removing the group represented by formula (d1) from the group represented by ; n D5 represents an integer greater than or equal to 1; The other symbols are as described above.

[0333] In equation (D2-4), D is R in equation (D2-1). 23 This represents the portion obtained by removing the group represented by formula (d1) from the group represented by . The branched structure represented by formula (D2-4) is preferably formed by the tertiary or quaternary carbon of the group represented by D.

[0334] In equations (D2-1) and (d1), X 2 These are, independently, -O-, -S-, or -N(R 24 ) represents X 2 The group represented by R may have 24 X represents a hydrogen atom, a monovalent hydrocarbon group having 1 to 20 carbon atoms, a monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms, or a group in which the hydrocarbon group or a part of the halogenated hydrocarbon group is substituted with at least one atom selected from oxygen and sulfur atoms. Note that two or more X 2 However, each of them is -N(R 24 )- If X 2 The group represented by has R 24 These may be the same or they may be different.

[0335] R 24 As a monovalent hydrocarbon group having 1 to 20 carbon atoms represented by formula (D1-1), R 1 This is similar to the "monovalent hydrocarbon group with 1 to 20 carbon atoms" as a substituent that the group represented by can have.

[0336] R 24 As a monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms represented by formula (D1-1), R 1 This is similar to the "monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms" as a substituent that the group represented by can have.

[0337] R 24 The "group in which a part of the hydrocarbon group or the halogenated hydrocarbon group is substituted with at least one selected from oxygen atoms and sulfur atoms" represented by formula (D1-1) is R 1 The substituents that the group represented by can have are the same as "a group in which a part of the hydrocarbon group or the halogenated hydrocarbon group is substituted with at least one selected from an oxygen atom and a sulfur atom."

[0338] Among them, R 24 From the viewpoint of excellent polymerization reactivity in the synthesis of component (D-2), it is preferable that this is a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms.

[0339] In formula (d1), ** represents a bonding site with another structural unit contained in component (D-2). Here, the other structural unit may be another structural unit represented by formula (D2-1) (hereinafter sometimes referred to as "structural unit (2')"), or it may be structural unit (1) (a structural unit represented by formula (D1-1)), other structural units (structural units other than structural unit (2) and structural unit (1)), or terminal groups represented by formula (y). Note that when ** in structural unit (2) bonds with structural unit (2'), ** in structural unit (2) is R in structural unit (2'). 21 The group represented by the X in the structural unit (2') is bonded to the X 2 It does not combine with it.

[0340] Component (D-2) preferably further contains structural unit (1) contained in component (D-1) in addition to structural unit (2). That is, in a preferred embodiment, component (D-2) further contains structural unit represented by the following formula (D1-1).

[0341] [ka]

[0342] (In formula (D1-1), R 1Each of these independently represents a divalent nitrogen-containing heteroaromatic group which may have substituents; R 2 Each of these independently represents a divalent organic group; X 1 These are, independently, -O-, -S-, or -N(R 3 )- represents; R 3 (This represents a hydrogen atom, a monovalent hydrocarbon group having 1 to 20 carbon atoms, a monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms, or a group in which the hydrocarbon group or a portion of the halogenated hydrocarbon group is substituted with at least one atom selected from oxygen and sulfur atoms.)

[0343] The structural unit (structural unit (1)) represented by formula (D1-1) is as described in the section on component (D-1) above.

[0344] In formula (y), Y represents a monovalent organic group having 3 to 50 carbon atoms that contains a radical polymerizable group other than a maleimide group. The group represented by Y in component (D-2) is the same as the group represented by Y in component (D-1). Therefore, in component (D-2), the group represented by Y preferably contains a monovalent aromatic group that contains a radical polymerizable group, more preferably a monovalent group selected from vinylphenyl, allylphenyl, isopropenylphenyl, and vinylbenzyl groups, and even more preferably vinylbenzyl.

[0345] If the group represented by Y is bonded to structural unit (2) in component (D-2), for example, then the group represented by Y is bonded to X in structural unit (2). 2 It bonds with the group represented by and R in structural unit (2) 21 It does not bond with X. Also, when the group represented by Y bonds with structural unit (1) in component (D-2), for example, the group represented by Y bonds with X in structural unit (1). 1 The group represented by the R in structural unit (1) is bonded to the R 1 It does not combine with it.

[0346] Component (D-2) may be synthesized by known methods. Component (D-2) may be, for example, R 21 Compounds that serve as raw materials for structures containing the group represented by R 22 -R 23 -R 22 Compounds that serve as raw materials for structures containing the group represented by , and compounds that serve as raw materials for structures containing the group represented by Y (and, if necessary, compounds that serve as raw materials for structural unit (1) and / or compounds that derive other structural units (structural units other than structural unit (2) and structural unit (1))) can be synthesized by heating them together with alkali metals or alkali metal compounds (and, if necessary, polymerization inhibitors) in an organic solvent. Compounds that serve as raw materials for structures containing the group represented by Y (and, if necessary, compounds that serve as raw materials for structural unit (1) and compounds that derive other structural units) are R 21 Compounds that serve as raw materials for structures containing the group represented by R 22 -R 23 -R 22 The compounds that serve as raw materials for a structure containing the group represented by may be reacted, and then heated, mixed, and reacted.

[0347] In the synthesis of component (D-2), R 21 Examples of compounds that serve as raw materials for structures containing the group represented by include, for example, the R used in the synthesis of component (D-1). 1 These compounds are similar to the raw materials for structures containing the group represented by . These compounds may be used individually or in combination of two or more.

[0348] In the synthesis of component (D-2), R 22 -R 23 -R 22 Examples of compounds that can serve as raw materials for structures containing the group represented by the formula (D2-5) below include the compounds represented by the formula (D2-5). The compounds represented by formula (D2-5) may be used individually or in combination of two or more.

[0349] [ka]

[0350] (In formula (D2-5), D' is n D6 Represents a hydrocarbon group with 1 to 20 carbon atoms in its valence; R 27 Each of these independently represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or a cycloalkyl group having 3 to 10 carbon atoms; n D6 This represents integers from 2 to 4; n D7 Each of these independently represents an integer from 1 to 5; n D8 Each of these independently represents an integer from 0 to 4, and 1 ≤ n D7 +n D8 (≤ 5.)

[0351] The compound represented by formula (D2-5) is preferably the compound represented by the following formula (D2-6-1) or formula (D2-6-2).

[0352] [ka]

[0353] (In equations (D2-6-1) and (D2-6-2), D', R 27 and n D6 These are D' and R in the above formula (D2-5), respectively. 27 and n D6 It is similar to this.

[0354] Specific examples of compounds represented by formula (D2-5) include, for example, the compounds shown in the following formula.

[0355] [ka]

[0356] In the synthesis of component (D-2), the compounds used as raw materials for the structure containing the group represented by Y are, for example, the same as the compounds used as raw materials for the structure containing the group represented by Y in the synthesis of component (D-1). These compounds may be used individually or in combination of two or more.

[0357] (D-2) If component contains structural unit (1), R in structural unit (1) 2 The compounds that serve as raw materials for structures containing the group represented by are as described in the section on the synthesis of component (D-1). These compounds may be used individually or in combination of two or more.

[0358] (D-2) If component contains other structural units (structural units other than structural unit (2) and structural unit (1)), examples of compounds that induce such other structural units include compounds that induce structural units containing carbonate bonds, thiocarbonate bonds, or selenocarbonate bonds, such as diphenyl carbonate, diphenylthiocarbonate, diphenylselenocarbonate, phosgene, thiophosgene, and selenophosgene; dihydroxy compounds such as benzenedimethanol and cyclohexanedimethanol; phosphine oxide compounds such as bis(fluorophenyl)phenylphosphine oxide, bis(fluorophenyl)naphthylphosphine oxide, and bis(fluorophenyl)anthrylphosphine oxide; and dihalides of dicarboxylic acids such as phthalate dichloride, isophthalate dichloride, and terephthalate dichloride. These compounds may be used individually or in combination of two or more.

[0359] In the synthesis of component (D-2), the alkali metal and alkali metal compound are the same as those used in the synthesis of component (D-1), for example. Therefore, the alkali metal and alkali metal compound used in the synthesis of component (D-2) are preferably alkali metal carbonates, and more preferably potassium carbonates.

[0360] In the synthesis of component (D-2), the organic solvent is, for example, the same as the organic solvent used in the synthesis of component (D-1). Therefore, the organic solvent used in the synthesis of component (D-2) is preferably 2-heptanone, cyclohexanone, N-methyl-2-pyrrolidone, toluene, and / or xylene, and more preferably N-methyl-2-pyrrolidone, 2-heptanone, and / or cyclohexanone.

[0361] In the synthesis of component (D-2), a polymerization inhibitor may be used to control the polymerization reaction and obtain component (D-2) having the desired molecular weight. The polymerization inhibitor used is the same as that used in the synthesis of component (D-1).

[0362] In the synthesis of component (D-2), R 21 Compounds that serve as raw materials for structures containing the group represented by R 22 -R 23 -R 22 The reaction temperature when reacting a compound that serves as a raw material for a structure containing the group represented by (and, if necessary, a compound that serves as a raw material for structural unit (1), and / or a compound that derives other structural units) is preferably 50°C or higher, more preferably 80°C or higher, preferably 300°C or lower, and more preferably 200°C or lower. The reaction time in the reaction is preferably 1 hour or more, more preferably 2 hours or more, even more preferably 3 hours or more, preferably 100 hours or less, more preferably 50 hours or less, and even more preferably 24 hours or less.

[0363] In the synthesis of component (D-2), R 21 Compounds that serve as raw materials for structures containing the group represented by R 22 -R 23 -R 22When a compound that serves as a raw material for a structure containing the group represented by is reacted, and then a compound that serves as a raw material for a structure containing the group represented by Y (and, if necessary, a compound that serves as a raw material for structural unit (1) and / or a compound that derives other structural units) is reacted, the reaction temperature is preferably 0°C or higher, more preferably 10°C or higher, preferably 130°C or lower, and more preferably 110°C or lower. The reaction time in this reaction is preferably 1 hour or more, more preferably 2 hours or more, even more preferably 3 hours or more, preferably 48 hours or less, more preferably 24 hours or less, and even more preferably 10 hours or less.

[0364] The weight-average molecular weight (Mw) of component (D-2) is, for example, 100 or more, preferably 1,000 or more, more preferably 2,000 or more, and even more preferably 3,000 or more. The upper limit of the weight-average molecular weight (Mw) of component (D-1) is, for example, 500,000 or less, preferably 100,000 or less, more preferably 50,000 or less, and even more preferably 30,000 or less or 20,000 or less. The weight-average molecular weight (Mw) of component (D-2) can be measured as a polystyrene equivalent value by gel permeation chromatography (GPC).

[0365] The content of structural unit (2) in component (D-2) is preferably 5 mol% or more, more preferably 10 mol% or more, even more preferably 20 mol% or more, preferably 95 mol% or less, more preferably 90 mol% or less, and even more preferably 80 mol% or less, when the total amount of structural units contained in component (D-2) is taken as 100 mol%.

[0366] If component (D-2) contains structural unit (1), the content of structural unit (1) in component (D-2) is preferably 5 mol% or more, more preferably 10 mol% or more, even more preferably 20 mol% or more, preferably 95 mol% or less, more preferably 90 mol% or less, and even more preferably 80 mol% or less, when the total amount of structural units contained in component (D-2) is taken as 100 mol%.

[0367] [Resin composition according to the third embodiment] The resin composition according to the third embodiment of the present invention includes (A) a TEMPO-based compound, (B) an inorganic filler, (C) a maleimide resin, and (D-3) a vinyl resin containing a radical polymerizable group having a vinyl structure and an active ester moiety. This provides a resin composition in which the dielectric loss tangent is reduced, crack resistance in desmear treatment is good, and plating penetration is suppressed.

[0368] The resin composition according to the third embodiment may contain any additional components in combination with components (A), (B), (C), and (D-3). Examples of optional components include (E) a curing accelerator, (F) a thermosetting monomer, (G) an organic filler, (H) a thermoplastic resin, (I) other additives, and (J) an organic solvent. The components included in the resin composition according to the third embodiment will be described in detail below.

[0369] The components (A) to (C) and (E) to (J) included in the resin composition according to the third embodiment may be the same as the components (A) to (C) and (E) to (J) included in the resin composition according to the first embodiment. The range of content of components (A) to (C) and (E) to (J) in the third embodiment may be the same as the range of content described for the resin composition according to the first embodiment. Each of the components (A) to (C) and (E) to (J) may be used individually or in combination of two or more types.

[0370] Note that (C) Miamide resin does not include components corresponding to (D-3). Unless otherwise specified, (E) curing accelerator does not include components (A) to (D-3) and components (F) to (H) mentioned above. Unless otherwise specified, (H) thermoplastic resin does not include components (A) to (G).

[0371] <(D-3) Vinyl resin containing a radical polymerizable group with a vinyl structure and an active ester moiety> The resin composition according to the third embodiment of the present invention includes a vinyl resin containing a radical polymerizable group having a vinyl structure and an active ester moiety as component (D-3). Hereinafter, the structure of component (D-3) may be referred to as the "third specific structure". Component (D-3) may be used alone or in combination of two or more types.

[0372] Component (D-3) contains an active ester moiety in one molecule. The active ester moiety contained in component (D-3) is preferably an aromatic ester skeleton. An aromatic ester skeleton represents a skeleton having an ester bond and an aromatic ring attached to one or both ends of the ester bond. Among these, an aromatic ester skeleton having aromatic rings at both ends of the ester bond is preferred. Examples of groups having such a skeleton include arylcarbonyloxy group, aryloxycarbonyl group, arylenecarbonyloxy group, aryleneoxycarbonyl group, arylcarbonyloxyarylene group, arylenecarbonyloxyarylene group, aryleneoxycarbonylarylene group, heteroarylcarbonyloxy group, heteroaryloxycarbonyl group, heteroarylenecarbonyloxy group, heteroaryleneoxycarbonyl group, heteroaryloxyarylene group, heteroaryloxy Examples include cyclocarbonylarylene groups, heteroarylenecarbonyloxyarylene groups, heteroaryleneoxycarbonylarylene groups, heteroarylcarbonyloxyheteroarylene groups, heteroaryloxycarbonylheteroarylene groups, heteroarylenecarbonyloxyheteroarylene groups, heteroaryleneoxycarbonylheteroarylene groups, heteroaryleneoxycarbonylheteroarylene groups, arylcarbonyloxyheteroarylene groups, aryloxycarbonylheteroarylene groups, arylenecarbonyloxyheteroarylene groups, and aryleneoxycarbonylheteroarylene groups. Furthermore, the number of carbon atoms in a group having such a skeleton is preferably 7 to 20, more preferably 7 to 15, and even more preferably 7 to 11.

[0373] The aryl group is preferably one having 6 to 30 carbon atoms, more preferably one having 6 to 20 carbon atoms, and even more preferably one having 6 to 10 carbon atoms. Examples of such aryl groups include phenyl, 1-methylphenyl, naphthyl, and anthracenyl groups. Here, the naphthyl group is a concept that includes both 1-naphthyl and 2-naphthyl groups.

[0374] A heteroaryl group refers to a monovalent group formed by removing one hydrogen atom from an aromatic heterocycle, which has heteroatoms such as oxygen, nitrogen, and sulfur atoms in addition to carbon atoms as ring constituent atoms. Heteroaryl groups with 3 to 30 carbon atoms are preferred, those with 4 to 20 carbon atoms are more preferred, and those with 6 to 10 carbon atoms are even more preferred. Examples of such heteroaryl groups include furyl, thienyl, pyrrolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, imidazolyl, pyridyl, pyridadinyl, pyrimidinyl, pyrazinyl, and triazinyl groups (e.g., 1,3,5-triazine-2-yl).

[0375] The arylene group is preferably one having 6 to 30 carbon atoms, more preferably one having 6 to 20 carbon atoms, and even more preferably one having 6 to 10 carbon atoms. Examples of such arylene groups include phenylene, naphthylene, anthracenylene, and biphenylene (-C6H4-C6H4-). Here, the phenylene group is a concept that includes 1,2-phenylene, 1,3-phenylene, and 1,4-phenylene groups, and the naphthylene group is a concept that includes 1,2-naphthylene, 1,3-naphthylene, 1,4-naphthylene, 1,5-naphthylene, 1,6-naphthylene, 1,7-naphthylene, and 1,8-naphthylene groups.

[0376] The heteroarylene group refers to a divalent group formed by removing one hydrogen atom from an aromatic heterocycle having, as ring-constituting atoms, in addition to carbon atoms, heteroatoms such as oxygen atom, nitrogen atom, and sulfur atom. As the heteroarylene group, a heteroarylene group having 3 to 30 carbon atoms is preferred, a heteroarylene group having 4 to 20 carbon atoms is more preferred, and a heteroarylene group having 6 to 10 carbon atoms is even more preferred. Examples of such a heteroarylene group include a pyrrolediyl group, a furandiyl group, a thiophenediyl group, a pyridinediyl group, a pyridazinediyl group, a pyrimidinediyl group, a pyrazinediyl group, a triazinediyl group, a piperidinediyl group, a triazolediyl group, a purinediyl group, a carbazolediyl group, a quinolinediyl group, an isoquinolinediyl group, and the like.

[0377] The aromatic ester skeleton, and aromatic groups such as an aryl group, an arylene group, a heteroaryl group, and a heteroarylene group may each have a substituent. The substituent is not particularly limited, and examples thereof include a halogen atom, -OH, -O-C 1-6 alkyl group, -N(C 1-10 alkyl group)2, an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an alkynyl group having 2 to 30 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, -NH2, -CN, -C(O)O-C 1-10 alkyl group, -COOH, -C(O)H, -NO2, a substituent containing a radical polymerizable group, and the like. Here, "C p-q " (p and q are each independently a positive integer and satisfy p<q) refers to that the number of carbon atoms of the organic group described immediately after this term is from p to q. For example, the expression "C 1-10 alkyl group" refers to an alkyl group having 1 to 10 carbon atoms. These substituents may be bonded to each other to form a ring, and the ring structure also includes a spiro ring and a fused ring. Details of the substituent containing a radical polymerizable group will be described later.

[0378] The term "aromatic group" refers to a group obtained by removing one or more hydrogen atoms from the aromatic ring of an aromatic compound. More specifically, a monovalent aromatic group is a group obtained by removing one hydrogen atom from the aromatic ring of an aromatic compound, and a divalent aromatic group is a group obtained by removing two hydrogen atoms from the aromatic ring of an aromatic compound. The term "aromatic ring" refers to a ring that obeys Hückel's rule, where the number of electrons in the π-electron system on the ring is 4n+2 (where n is a natural number), and includes monocyclic aromatic rings and fused polycyclic aromatic rings formed by the fusion of two or more monocyclic aromatic rings. Aromatic rings can be carbocyclic rings or heterocyclic rings having heteroatoms such as oxygen, nitrogen, or sulfur atoms.

[0379] The number of active ester sites contained in one molecule of component (D-3) is, for example, one or more, preferably two or more.

[0380] Component (D-3) contains a radical polymerizable group. A radical polymerizable group is a group containing a radically polymerizable ethylenically unsaturated bond. Ethylenelycol unsaturated bonds do not include reaction-inert unsaturated bonds that constitute aromatic groups such as benzene rings.

[0381] (D-3) Component includes resins containing a substituent with a radical polymerizable group (D-3-1) and an active ester moiety, and resins containing a skeleton with a radical polymerizable group (D-3-2) and an active ester moiety.

[0382] The terminal end of component (D-3-1) is preferably a monovalent aromatic group. An example of a monovalent aromatic group is an aryl group, as described above. Among these, a phenyl group is preferred as the monovalent aromatic group at the terminal end of component (B-1).

[0383] Component (D-3-1) may have a substituent containing a radical polymerizable group having a vinyl structure, an active ester moiety, and any of the following groups: an aromatic group, an aliphatic group, an oxygen atom, or a combination thereof.

[0384] (D-3-1) The aromatic group that component may have is preferably a divalent aromatic group, more preferably an arylene group or an aralkylene group, and even more preferably an arylene group. The arylene group is as described above. As for the aralkylene group, an aralkylene group having 7 to 30 carbon atoms is preferred, an aralkylene group having 7 to 20 carbon atoms is more preferred, and an aralkylene group having 7 to 15 carbon atoms is even more preferred. Among these, the phenylene group is preferred.

[0385] (D-3-1) The aliphatic groups that component may have are preferably divalent aliphatic groups, more preferably divalent saturated aliphatic groups, and even more preferably alkylene groups and cycloalkylene groups. The alkylene groups are preferably alkylene groups having 1 to 10 carbon atoms, more preferably alkylene groups having 1 to 6 carbon atoms, and even more preferably alkylene groups having 1 to 3 carbon atoms. Examples of alkylene groups include methylene groups, ethylene groups, propylene groups, 1-methylmethylene groups, 1,1-dimethylmethylene groups, 1-methylethylene groups, 1,1-dimethylethylene groups, 1,2-dimethylethylene groups, butylene groups, 1-methylpropylene groups, 2-methylpropylene groups, 1,1-dimethyl-3-methylpropylene groups, pentylene groups, hexylene groups, etc., with 1,1-dimethylmethylene groups being preferred.

[0386] The cycloalkylene group is preferably a cycloalkylene group having 3 to 20 carbon atoms, more preferably a cycloalkylene group having 3 to 15 carbon atoms, and even more preferably a cycloalkylene group having 5 to 10 carbon atoms. The cycloalkylene group may have a monocyclic or polycyclic structure. Examples of cycloalkylene groups include cyclopropylene, cyclobutylene, cyclopentylene, cyclohexylene, cyclopentylene, cycloheptylene, and cycloalkylene groups represented by the following formulas (a) to (d). In formulas (a) to (d), "*" represents a bond.

[0387] [ka]

[0388] (D-3-1) The "groups consisting of these combinations" that the component may have are preferably divalent groups, such as groups consisting of a combination of an aliphatic group and an aromatic group, or groups consisting of a combination of an aromatic group, an aliphatic group and an aromatic group. One embodiment of these groups consisting of these combinations is a group consisting of an arylene-alkylene-arylene combination, and a group consisting of a phenylene-1,1-dimethylmethylene-phenylene combination is preferred.

[0389] The aromatic and aliphatic groups that component (D-3-1) may have may further have substituents. These substituents are the same as those that the aromatic ester skeleton may have.

[0390] In component (D-3-1), examples of radical polymerizable groups having a vinyl structure include unsaturated hydrocarbon groups such as vinyl groups, propenyl groups (allyl group, 1-propenyl group, isopropenyl group), butenyl groups (1-butenyl group, clotyl group, methallyl group, isoclotyl group, etc.), pentenyl groups (1-pentenyl group, etc.), hexenyl groups (1-hexenyl group, etc.), heptenyl groups (1-heptenyl group, etc.), octenyl groups (1-octenyl group, etc.), cyclopentenyl groups (2-cyclopentenyl group, etc.), and cyclohexenyl groups (3-cyclohexenyl group, etc.); and α,β-unsaturated carbonyl groups such as acryloyl groups, methacryloyl groups, and maleimide groups (2,5-dihydro-2,5-dioxo-1H-pyrrole-1-yl group). In particular, component (D-3-1) preferably contains an allyl group as a substituent containing a radical polymerizable group having a vinyl structure.

[0391] The number of radical polymerizable groups having a vinyl structure per molecule of component (D-3-1) is preferably 1 or more, more preferably 2 or more, preferably 10 or less, more preferably 8 or less, and even more preferably 5 or less.

[0392] The "substituent containing a radical polymerizable group having a vinyl structure" contained in component (D-3-1) may be a substituent on a terminal monovalent aromatic group, or it may be a substituent on an aromatic group or an aliphatic group. When component (D-3-1) contains the "substituent containing a radical polymerizable group having a vinyl structure" as a substituent on a terminal monovalent aromatic group, it is preferable that component (D-3-1) contains the "substituent containing a radical polymerizable group having a vinyl structure" as substituents on aromatic groups at both ends.

[0393] Component (D-3-1) preferably contains either a vinyl resin represented by the following general formula (D-3-i) or a vinyl resin represented by the following general formula (D-3-ii), and more preferably contains a vinyl resin represented by the general formula (D-3-i).

[0394] [ka]

[0395] (In equations (D-3-i) and (D-3-ii), Ar 11 Each of these independently represents a monovalent aromatic group which may have substituents; Ar 12 Each of these independently represents a divalent aromatic group which may have substituents; R 11 Each of these independently represents a divalent aromatic group which may have substituents, a divalent aliphatic group which may have substituents, an oxygen atom, a sulfur atom, or a divalent group which is a combination thereof; Ar 11 Ar 12 , and R 11 At least one of them has a substituent containing a radical polymerizable group having a vinyl structure; m1, n1, m2, and n2 each independently represent an integer of 0 or greater than or equal to 1.

[0396] In equations (D-3-i) and (D-3-ii), Ar 11Each of these independently represents a monovalent aromatic group which may have substituents. The definitions of monovalent aromatic groups are as described above. In formulas (D-3-i) and (D-3-ii), Ar 11 They may be the same or different from each other, but it is preferable that they be the same. Also, Ar 11 The group is preferably a phenyl group, a 1-naphthyl group, or a 2-naphthyl group, with a phenyl group or a 1-naphthyl group being more preferred.

[0397] Ar 11 The substituents that it may have are the same as those that the aromatic ester skeleton may have. Among them, Ar 11 If the compound has substituents, it is preferable that the substituents contain radical polymerizable groups having a vinyl structure.

[0398] In equations (D-3-i) and (D-3-ii), Ar 12 Each of these independently represents a divalent aromatic group which may have substituents. Divalent aromatic groups are as described above. Among them, Ar 12 A phenylene group is preferred, and a 1,3-phenylene group is more preferred.

[0399] Ar 12 The substituents that it may have are the same as those that the aromatic ester skeleton may have. Among them, Ar 12 It is preferable that the compound has an aralkyl group as a substituent, and more preferably a benzyl group as a substituent.

[0400] In equations (D-3-i) and (D-3-ii), R 11 Each of these independently represents a divalent aromatic group which may have substituents, a divalent aliphatic group which may have substituents, an oxygen atom, a sulfur atom, or a divalent group which is a combination thereof. The divalent aromatic group is as described above.

[0401] R 11The divalent aliphatic group represented by is preferably a divalent saturated aliphatic group, more preferably an alkylene group or a cycloalkylene group, and even more preferably a cycloalkylene group. The alkylene group and the cycloalkylene group are as described above.

[0402] R 11 The term "divalent group consisting of these combinations" refers to a divalent group consisting of a combination of a divalent aromatic group which may have substituents, a divalent aliphatic group which may have substituents, an oxygen atom, and / or a sulfur atom. Among these, R 11 Preferably, the divalent group is a combination of these (i.e., a divalent group consisting of a combination of a divalent aromatic group which may have substituents, a divalent aliphatic group which may have substituents, an oxygen atom, and / or a sulfur atom). The divalent group is preferably a combination of a divalent aromatic group which may have substituents and a divalent aliphatic group which may have substituents, and more preferably a divalent group which alternates between a plurality of divalent aromatic groups which may have substituents and a plurality of divalent aliphatic groups which may have substituents. Specific examples of the above divalent group include the divalent groups (D-3-1) to (D-3-13) below, of which (D-3-10) and (D-3-11) are preferred. In the formula, d1 to d9 represent integers from 0 to 10, preferably integers from 0 to 6, and more preferably integers from 0 to 5. In formulas (D-3-1) to (D-3-13), "*" represents a bond, and the wavy line represents the structure obtained by the reaction of the aromatic compound, the acid halide of the aromatic compound, or the esterified product of the aromatic compound used in the synthesis of component (D-3-1).

[0403] [ka]

[0404] [ka]

[0405] R 11 The substituents that may be present are the same as those that may be present on the aromatic ester skeleton.

[0406] In formula (D-3-i), m1 represents 0 or an integer greater than or equal to 1, preferably an integer between 0 and 10, more preferably an integer between 0 and 8, even more preferably an integer between 0 and 6, and even more preferably 0.

[0407] In formula (D-3-i), n1 represents 0 or an integer greater than or equal to 1, preferably an integer between 0 and 30, more preferably an integer between 3 and 30, and even more preferably an integer between 6 and 30.

[0408] In formula (D-3-ii), m2 and n2 each independently represent an integer of 0 or 1 or more, preferably an integer between 0 and 20, more preferably an integer between 0 and 15, even more preferably an integer between 0 and 10, and even more preferably an integer between 0 and 6.

[0409] The vinyl resin represented by formula (D-3-i) is preferably the vinyl resin represented by the following general formula (D-3-ia).

[0410] [ka]

[0411] (In formula (D-3-ia), Ar 21 Each of these independently represents a monovalent aromatic group having at least an allyl group as a substituent; Ar 22 Each of these independently represents a divalent aromatic group which may have substituents; R 21 Each of these independently represents a divalent aromatic group which may have substituents, a divalent aliphatic group which may have substituents, an oxygen atom, a sulfur atom, or a divalent group which is a combination thereof; m3 and n3 each independently represent an integer of 0 or greater than or equal to 1.

[0412] In equation (D-3-ia), Ar 21 Each of these independently represents a monovalent aromatic group having at least an allyl group as a substituent. Monovalent aromatic groups are as described above. In formula (D-3-ia), Ar 21 They may be the same or different from each other, but it is preferable that they be the same. 21 The group is preferably a phenyl group, a 1-naphthyl group, or a 2-naphthyl group, with a phenyl group or a 1-naphthyl group being more preferred.

[0413] Ar 21 The compound may have substituents other than the allyl group. These substituents are the same as those that may be present on the aromatic ester skeleton.

[0414] In equation (D-3-ia), Ar 22 Each of these independently represents a divalent aromatic group which may have substituents, and in formula (D-3-i) Ar 12 It is similar to that.

[0415] In equation (D-3-ia), R 21 Each independently represents a divalent aromatic group which may have substituents, a divalent aliphatic group which may have substituents, an oxygen atom, a sulfur atom, or a divalent group which is a combination thereof, and R in formula (D-3-i) 11 It is similar to that.

[0416] In equation (D-3-ia), m3 represents an integer of 0 or greater than or equal to 1, and is the same as m1 in equation (D-3-i). Also, in equation (D-3-ia), n3 represents an integer of 0 or greater than or equal to 1, and is the same as n1 in equation (D-3-i).

[0417] Specific examples of component (D-3-1) include the following compounds (D-3i) to (D-3iv). Furthermore, specific examples of component (D-3-1) include the compounds described in paragraphs 0068 to 0071 of International Publication No. 2018 / 235424 and paragraphs 0113 to 0115 of International Publication No. 2018 / 235425. However, component (D-3-1) is not limited to these specific examples. In the formula, a represents an integer from 0 to 6; s represents an integer of 0 or greater than or equal to 1; r represents an integer from 1 to 10; and n and m represent an integer of 0 or greater than or equal to 1.

[0418] [ka]

[0419] Component (D-3-1) may be synthesized by known methods. Component (D-3-1) can be synthesized, for example, by the method described in International Publication No. 2018 / 235424 or International Publication No. 2018 / 235425.

[0420] In component (D-3-2), the butadiene skeleton is an example of a skeleton containing a radical polymerizable group having a vinyl structure. The butadiene skeleton represents the carbon skeleton contained in the butenediyl group. Here, the butenediyl group includes the 2-butene-1,4-diyl group and the 3-butene-1,2-diyl group (i.e., the vinylethylene group). The aforementioned 2-butene-1,4-diyl group may be in the cis or trans form. Hereinafter, a structure containing the butadiene skeleton may be appropriately referred to as the "butadiene structure". This butadiene structure includes the aforementioned 2-butene-1,4-diyl group and the 3-butene-1,2-diyl group, as well as groups in which the hydrogen atoms contained in these groups are substituted with substituents. Examples of substituents include halogen atoms; saturated aliphatic hydrocarbon groups such as alkyl groups and cycloalkyl groups; aromatic hydrocarbon groups such as aryl groups; hydrocarbon oxy groups such as alkoxy groups, cycloalkyloxy groups, and aryloxy groups.

[0421] Preferred examples of butadiene structures include those represented by the following formulas (D-3-14) to (D-3-15).

[0422] [ka]

[0423] (In equations (D-3-14) and (D-3-15), R b Each of these independently represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms; * represents a bonding site.

[0424] In equations (D-3-14) and (D-3-15), R b Each of these independently represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms. Rb is preferably a hydrogen atom or a halogen atom, and more preferably a hydrogen atom.

[0425] Component (D-3-2) preferably includes a butadiene structure represented by formula (D-3-14) as a structure having a butadiene skeleton. In such preferred embodiments, component (D-3-2) may include only the butadiene structure represented by formula (D-3-14) as a structure having a butadiene skeleton, or it may include a combination of the butadiene structure represented by formula (D-3-14) and the butadiene structure represented by formula (D-3-15).

[0426] The number of butadiene structures contained in one molecule of component (D-3-2) is, for example, one or more, preferably two or more. In particular, it is more preferable that component (D-3-2) contains a polybutadiene structure in which two or more butadiene structures are bonded to each other.

[0427] Component (D-3-2) is preferably a vinyl resin represented by the following formula (D-3-iii).

[0428] [ka]

[0429] (In formula (D-3-iii), Ar 1 Each of these independently represents a monovalent aromatic group which may have substituents; Ar 2 Each of these independently represents a divalent aromatic group which may have substituents; R 1 Each of these independently represents a divalent aliphatic group which may have substituents; R 2 Each of these independently represents a butadiene structure; m4 and n4 each independently represent an integer of 0 or greater than or equal to 1.

[0430] In equation (D-3-iii), Ar 1 Each of these independently represents a monovalent aromatic group which may have substituents, and in formula (D-3-i) Ar 11 This is similar to the monovalent aromatic group represented by . In particular, Ar 1 A 1-methylphenyl group is preferred.

[0431] In equation (D-3-iii), Ar 2 Each of these independently represents a divalent aromatic group which may have substituents, and in formula (D-3-i) Ar 12 This is similar to the divalent aromatic group represented by .

[0432] In equation (D-3-iii), R 1 Each of these independently represents a divalent aliphatic group which may have substituents. 1 The divalent aliphatic group represented by may be linear, branched, or cyclic. 1 The number of carbon atoms in the divalent aliphatic group represented by is preferably 1 to 12, more preferably 1 to 6, and even more preferably 1 to 4. The number of carbon atoms in substituents is not included in this number. Examples of divalent aliphatic groups include alkylene groups and alkenylene groups.

[0433] R 1The alkylene group represented by may be linear, branched, or cyclic. Specific examples of alkylene groups are as described above.

[0434] R 1 The alkenylene group represented by may be linear, branched, or cyclic. Examples of alkenylene groups include etenylene, propenylene, butenylene, pentenylene, hexenylene, cyclopropenylene, cyclobutenylene, cyclopentenylene, cyclohexenylene, norborneylene, and the like.

[0435] In equation (D-3-iii), R 2 Each of these independently represents a butadiene structure. The butadiene structure is as described above.

[0436] In formula (D-3-iii), m4 represents an integer of 0 or greater than or equal to 1, preferably an integer between 0 and 10, more preferably an integer between 0 and 8, and even more preferably an integer between 0 and 6. Each n4 independently represents an integer of 0 or greater than or equal to 1, preferably an integer of 1 or greater, more preferably an integer of 3 or greater, and even more preferably an integer of 6 or greater. The upper limit of n4 is preferably an integer of 50 or less, more preferably an integer of 40 or less, and even more preferably an integer of 30 or less.

[0437] Ar 1 A monovalent aromatic group represented by Ar 2 A divalent aromatic group represented by R 1 Each of the divalent aliphatic groups represented by may have substituents. These substituents are the same as those that may be present on the aromatic ester skeleton.

[0438] A specific example of the vinyl resin represented by formula (D-3-iii) is the vinyl resin represented by the following formula (D-3-iii-a). However, the component (D-3-2) is not limited to this specific example. Ar in formula (D-3-iii-a) 1 m4 and n4 are, respectively, Ar in equation (D-3-iii). 1This is the same as m4 and n4.

[0439] [ka]

[0440] Component (D-3) preferably contains either component (D-3-1) or component (D-3-2). Therefore, component (D-3) preferably contains one or more vinyl resins selected from the group consisting of vinyl resins represented by formula (D-3-i), vinyl resins represented by formula (D-3-ii), and vinyl resins represented by formula (D-3-iii), more preferably contains at least one of vinyl resins represented by formula (D-3-i) and vinyl resins represented by formula (D-3-iii), and even more preferably contains vinyl resins represented by formula (D-3-i).

[0441] The weight-average molecular weight (Mw) of component (D-3) is preferably 150 or more, more preferably 200 or more, even more preferably 250 or more, preferably 3,000 or less, more preferably 2,000 or less, and even more preferably 1,500 or less. The weight-average molecular weight (Mw) of component (B) is the weight-average molecular weight on a polystyrene basis measured by gel permeation chromatography (GPC).

[0442] [Method for producing resin composition] The resin composition of the present invention can be manufactured, for example, by mixing components that may be included in the resin composition. Therefore, the resin composition can be manufactured by a manufacturing method that includes the step of mixing (A) a TEMPO-based compound, (B) an inorganic filler, (C) a maleimide resin, and (D) a vinyl resin having a specific structure. This manufacturing method may also include the step of mixing any components such as components (E) to (J). Components (A) to (J) may be mixed partially or entirely at the same time, or sequentially. Furthermore, this manufacturing method may, if necessary, include kneading or stirring (mixing) the resin composition using kneading means such as a three-roll mill, ball mill, bead mill, or sand mill, or stirring means such as a super mixer, planetary mixer, or high-speed rotary mixer.

[0443] [Properties of resin compositions and their cured products] The resin composition of the present invention comprises (A) a TEMPO-based compound, (B) an inorganic filler, (C) a maleimide resin, and (D) a vinyl resin having a specific structure, wherein component (D) is a resin selected from the group consisting of components (D-1), (D-2), and (D-3). The resin composition of the present invention, in combination with components (A) to (D), further optionally includes (E) a curing accelerator, (F) a thermosetting monomer, (G) an organic filler, (H) a thermoplastic resin, (I) other additives, (J) an organic solvent, etc., thereby reducing the dielectric loss tangent, providing a resin composition with good crack resistance in desmear treatment and suppressed plating penetration. Furthermore, an insulating layer can be formed by the cured product of this resin composition. Normally, heat is applied when a resin composition is cured, so among the components contained in the resin composition, volatile components such as (I) organic solvents may volatilize due to the heat during curing. Therefore, the cured product obtained by curing the resin composition may contain non-volatile components such as components (A) to (I) or their reaction products.

[0444] The cured product of the resin composition of the present invention can have a low dielectric loss tangent Df. When the resin composition of the present invention is heat-cured in air, for example at 200°C for 90 minutes, the dielectric loss tangent Df of the cured product is preferably 0.0025 or less, more preferably 0.0023 or less, and even more preferably 0.0021 or less. There is no particular lower limit to the dielectric loss tangent Df, and it may be, for example, 0.0010 or more. The dielectric loss tangent Df when cured in air can be measured according to the method described in the section "<Test Example 1: Measurement of Dielectric Properties (Dielectric Constant, Dielectric Loss Tangent) (Curing in an Atmospheric Atmosphere)>" described later.

[0445] When the cured resin composition of the present invention is heat-cured under a nitrogen atmosphere (N2), for example at 200°C for 90 minutes, it is less susceptible to oxidation than when heat-cured under air, resulting in a further reduction in dielectric loss tangent. In one example, the dielectric loss tangent Df of the cured product is preferably 0.0020 or less, more preferably 0.0019 or less, and even more preferably 0.0018 or less. There is no particular lower limit to the dielectric loss tangent Df, and it can be, for example, 0.0010 or more. The dielectric loss tangent Df when cured under a nitrogen atmosphere can be measured according to the method described in the section "<Test Example 2: Measurement of Dielectric Properties (Dielectric Constant, Dielectric Loss Tangent) (Curing under a Nitrogen Atmosphere)>" described later.

[0446] The ratio of the dielectric loss tangent (Air) when cured in air to the dielectric loss tangent (N2) when cured in a nitrogen atmosphere (N2) [dielectric loss tangent (N2) / dielectric loss tangent (Air)] is preferably less than 1, more preferably 0.95 or less, and even more preferably 0.9 or less. The dielectric loss tangent (N2) / dielectric loss tangent (Air) can be calculated by measuring according to the method described in the section "<Test Example 3: Calculation of Dielectric Loss Tangent (N2 / Air)>" below.

[0447] A cured product of the resin composition of the present invention, for example, cured at 100°C for 30 minutes followed by 190°C for 30 minutes, exhibits the property of suppressing the occurrence of cracks after desmearing (roughening treatment). Therefore, it provides an insulating layer with excellent crack resistance. Specifically, when 100 copper pads of a circuit board are observed after fabrication and desmearing, the number of cracks may preferably be 10 or more and less than 20, more preferably less than 10. Crack resistance can be evaluated according to the method described in the section <Test Example 4: Evaluation of Crack Resistance> described later.

[0448] The resin composition of the present invention is characterized by producing a cured product with good adhesion strength (plating peel strength) to the plated conductor layer. Therefore, when an insulating layer is formed using the resin composition of the present invention, an insulating layer with good peel strength to the plated conductor layer can be obtained. The peel strength between the resin composition and the plated conductor layer is preferably 0.3 kgf / cm or more, more preferably 0.35 kgf / cm or more, and even more preferably 0.4 kgf / cm or more. The upper limit of the peel strength is preferably higher, and may be, for example, 2 kgf / cm or less. The peel strength can be measured according to the method described in the section "<Test Example 5: Evaluation of Substrate Adhesion>" described later.

[0449] An insulating layer made using the resin composition of the present invention has the characteristic of suppressing penetration during the plating process. For example, when tested under the <Electroless Copper Plating Penetration Test Conditions> described below, the penetration depth of the electroless copper plating is preferably 1.2 μm or less, more preferably 1.0 μm or less, even more preferably less than 1.0 μm, 0.95 μm or less, 0.90 μm or less, or 0.85 μm or less. More detailed conditions for the <Plating Penetration Test Conditions> are described in the <Test Example 6: Evaluation of Plating Penetration> section below.

[0450] <Uses of resin compositions> The resin composition of the present invention can be used for forming insulating layers, and is particularly preferred for forming insulating layers on circuit boards. The resin composition may also be used for manufacturing resin sheets. Typically, insulating layers are formed using these resin sheets. The resin composition may also be used for other applications, such as solder resist, underfill material, die bonding material, hole-filling resin, sealing resin, and component embedding resin.

[0451] <Resin sheet> A resin sheet according to one embodiment of the present invention comprises a support and a resin composition layer formed on the support. The resin composition layer contains the above-described resin composition, and preferably contains only the above-described resin composition.

[0452] From the viewpoint of thinning, the thickness of the resin composition layer of the resin sheet is preferably 200 μm or less, more preferably 150 μm or less, and even more preferably 100 μm or less. The lower limit of the thickness of the resin composition layer may be, for example, 1 μm or more, 3 μm or more, 5 μm or more, etc.

[0453] Examples of support materials include plastic film, metal foil, and release paper, with plastic film and metal foil being preferred.

[0454] When using a plastic film as a support, examples of plastic materials include polyesters such as polyethylene terephthalate (hereinafter sometimes abbreviated as "PET") and polyethylene naphthalate (hereinafter sometimes abbreviated as "PEN"), polycarbonate (hereinafter sometimes abbreviated as "PC"), acrylics such as polymethyl methacrylate (PMMA), cyclic polyolefins, triacetylcellulose (TAC), polyether sulfide (PES), polyether ketones, and polyimides. Among these, polyethylene terephthalate and polyethylene naphthalate are preferred, and inexpensive polyethylene terephthalate is particularly preferred.

[0455] When using metal foil as a support, examples of metal foil include copper foil and aluminum foil, with copper foil being preferred. As for copper foil, foil made of single-metal copper may be used, or foil made of an alloy of copper with another metal (for example, tin, chromium, silver, magnesium, nickel, zirconium, silicon, titanium, etc.) may be used.

[0456] The support may have surface treatments such as matte finish, corona treatment, or antistatic treatment applied to the surface that bonds with the resin composition layer.

[0457] As the support, a support with a release layer may be used, which has a release layer on the surface that is bonded to the resin composition layer. Examples of release agents used in the release layer of the support with a release layer include one or more release agents selected from the group consisting of alkyd-based release agents, polyolefin-based release agents, urethane-based release agents, and silicone-based release agents. Commercially available products may be used as the support with a release layer, for example, PET films having a release layer mainly composed of a silicone-based release agent or an alkyd resin-based release agent, such as "PET501010", "SK-1", "AL-5", and "AL-7" from Lintec Corporation; "Lumirror T60" from Toray Industries, Inc.; "Purex" from Teijin Ltd.; and "Unipeel" from Unitika Corporation.

[0458] The thickness of the support is not particularly limited, but is preferably 1 μm or more, more preferably 5 μm or more, even more preferably 10 μm or more, preferably 75 μm or less, more preferably 60 μm or less, and even more preferably 50 μm or less. When using a support with a release layer, it is preferable that the overall thickness of the support with the release layer is within the above range.

[0459] When using metal foil as a support, a metal foil with a support substrate, which is formed by laminating a peelable support substrate onto a thin metal foil, may be used. In one embodiment, the metal foil with a support substrate includes a support substrate, a release layer provided on the support substrate, and a metal foil provided on the release layer. When using metal foil with a support substrate as a support, the resin composition layer is provided on the metal foil.

[0460] In a metal foil with a support substrate, the material of the support substrate is not particularly limited, but examples include copper foil, aluminum foil, stainless steel foil, titanium foil, copper alloy foil, etc. When copper foil is used as the support substrate, it may be electrolytic copper foil or rolled copper foil. Furthermore, the release layer is not particularly limited as long as it can be used to peel the metal foil from the support substrate, and examples include an alloy layer of elements selected from the group consisting of Cr, Ni, Co, Fe, Mo, Ti, W, and P; an organic coating, etc.

[0461] In a metal foil with a support substrate, the material of the metal foil is preferably, for example, copper foil or copper alloy foil.

[0462] In a metal foil with a support substrate, the thickness of the support substrate is not particularly limited, but is preferably in the range of 10 μm to 150 μm, and more preferably in the range of 10 μm to 100 μm. The thickness of the metal foil may be, for example, in the range of 0.1 μm to 10 μm.

[0463] The resin sheet may include any components as needed. For example, the resin sheet may include a protective film to protect the resin composition layer. The protective film is usually provided on the side of the resin composition layer that is not bonded to the support (i.e., the side opposite to the support). The thickness of the protective film is not particularly limited, but is, for example, 1 μm to 40 μm. When a protective film is provided, the adhesion of dust and scratches to the surface of the resin composition layer can be suppressed.

[0464] A resin sheet can be manufactured, for example, by a method that includes forming a resin composition layer on a support. Specifically, a resin sheet may be manufactured by applying a resin varnish as a resin composition onto a support and then drying it to form a resin composition layer.

[0465] The resin composition can be applied using a coating device such as a die coater. Drying can be carried out by drying methods such as heating or hot air blowing. The drying conditions are not particularly limited, but the solvent content in the resin composition layer is usually 10% by mass or less, preferably 5% by mass or less. Although this may vary depending on the boiling point of the solvent, for example, when using a resin composition containing 30% to 60% by mass of solvent, the resin composition layer can be formed by drying at 50°C to 150°C for 3 to 10 minutes.

[0466] The manufactured resin sheets can be stored by rolling them up. If the resin sheets have a protective film, they can usually be used after removing the protective film.

[0467] <Circuit board> A circuit board according to one embodiment of the present invention includes a cured product of the resin composition described above. Typically, a circuit board has a cured product layer, and this cured product layer includes a cured product of the resin composition. The cured product layer may contain only a cured product of the resin composition. The cured product layer can be used as an insulating layer, such as an interlayer insulating layer. The thickness of the cured product layer is not particularly limited and can be, for example, in the same range as the thickness of the resin composition layer of a resin sheet. Furthermore, the cured product layer can usually have properties similar to those of the cured product of the resin composition described above.

[0468] Preferably, the circuit board comprises an inner layer substrate, and the cured material layer is provided on this inner layer substrate as an insulating layer. The circuit board may also comprise a conductive layer. For example, a conductive layer may be provided on the insulating layer. An example of a preferred method for manufacturing a circuit board will be described below.

[0469] A preferred example of a method for manufacturing a circuit board is: Step (I) of forming a resin composition layer on an inner layer substrate, (II) A step of curing the resin composition layer and Includes.

[0470] An "internal layer substrate" is a material that serves as the base for a circuit board, and examples include glass epoxy substrates, metal substrates, polyester substrates, polyimide substrates, BT resin substrates, thermosetting polyphenylene ether substrates, etc. An internal layer substrate may have a conductive layer on one or both sides. The conductive layer on the internal layer substrate may be patterned. Circuit wiring can be formed using a patterned conductive layer. An internal layer substrate with conductive layers formed on one or both sides is sometimes called an "internal layer circuit board." Intermediate products on which an insulating layer and / or a conductive layer is further formed during the manufacturing of a circuit board are also included in the term "internal layer substrate." An internal layer substrate with embedded components may also be used.

[0471] From the viewpoint of taking advantage of the benefit of suppressing the formation of large particles due to the precipitation of components in the resin varnish, it is preferable that the minimum line-and-space (L / S) of the circuit wiring on the circuit board to which the resin composition according to the above embodiment is applied is small. Unless otherwise specified, "line" refers to the wiring width of the circuit wiring, and "space" refers to the spacing between wirings. The range of the minimum line-and-space ratio is preferably 10 μm / 10 μm or less, more preferably 5 μm / 5 μm or less, even more preferably 3 μm / 3 μm or less, preferably 0.1 μm / 0.1 μm or more, more preferably 0.5 μm / 0.5 μm or more, and even more preferably 1 μm / 1 μm or more. The wiring pitch of the circuit wiring is preferably 20 μm or less, more preferably 10 μm or less, even more preferably 6 μm or less, preferably 0.2 μm or more, more preferably 1 μm or more, and even more preferably 2 μm or more. The line-and-space (L / S) and wiring pitch may be uniform or non-uniform throughout the entire conductor layer.

[0472] The formation of a resin composition layer on an inner layer substrate may be carried out by a formation method that includes, for example, applying a resin composition such as a resin varnish to the inner layer substrate and drying it as necessary, but it is preferable to use a resin sheet. The method for forming a resin composition layer using a resin sheet usually involves laminating the resin sheet and the inner layer substrate. The lamination of the resin sheet and the inner layer substrate is carried out so that the resin composition layer of the resin sheet and the inner layer substrate are joined. This lamination may be carried out, for example, by heating and pressing the resin sheet to the inner layer substrate from the support side. Examples of a member for heating and pressing the resin sheet to the inner layer substrate (hereinafter also referred to as the "heat-pressing member") include a heated metal plate (such as a SUS end plate) or a metal roll (such as a SUS roll). It is preferable to press the resin sheet via an elastic material such as heat-resistant rubber so that the resin sheet can sufficiently follow the surface irregularities of the inner layer substrate, rather than pressing the heat-pressing member directly onto the resin sheet.

[0473] Lamination of the inner layer substrate and the resin sheet may be carried out by a vacuum lamination method. In the vacuum lamination method, the heat-pressure temperature is preferably in the range of 60°C to 160°C, more preferably in the range of 80°C to 140°C, the heat-pressure pressure is preferably in the range of 0.098 MPa to 1.77 MPa, more preferably in the range of 0.29 MPa to 1.47 MPa, and the heat-pressure time is preferably in the range of 20 seconds to 400 seconds, more preferably in the range of 30 seconds to 300 seconds. Lamination is preferably carried out under reduced pressure conditions of 26.7 hPa or less.

[0474] Lamination may be performed using a commercially available vacuum laminator. Examples of commercially available vacuum laminators include vacuum pressure laminators manufactured by Meiki Seisakusho Co., Ltd., vacuum applicators manufactured by Nikko Materials Co., Ltd., and batch-type vacuum pressure laminators.

[0475] The method for manufacturing a circuit board may include, after lamination, a smoothing treatment of the resin sheet by pressing a heat-pressure bonding member from the support side under normal pressure (atmospheric pressure). The pressing conditions for the smoothing treatment may be the same as the conditions for the heat-pressure bonding of the lamination. The smoothing treatment can be performed using a commercially available laminator. Lamination and smoothing may be performed continuously using the commercially available vacuum laminator.

[0476] The method for manufacturing a circuit board according to this example includes a step (II) in which a resin composition layer is cured after step (I). By curing the resin composition layer in step (II), an insulating layer can be formed as a cured product layer containing the cured resin composition.

[0477] The resin composition layer is usually cured by thermal curing. The thermal curing conditions for the resin composition layer may vary depending on the type of resin composition. For example, the curing temperature is preferably 120°C to 240°C, more preferably 150°C to 220°C, and even more preferably 170°C to 210°C. The curing time may be preferably 5 minutes to 120 minutes, more preferably 10 minutes to 100 minutes, and even more preferably 15 minutes to 100 minutes.

[0478] The method for manufacturing a circuit board may include preheating the resin composition layer at a temperature lower than the curing temperature before the resin composition layer is heat-cured. For example, prior to heat-curing the resin composition layer, the resin composition layer may be preheated at a temperature of typically 50°C to 150°C, preferably 60°C to 140°C, more preferably 70°C to 130°C for typically 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. Preheating is usually performed after step (I). Also, if a smoothing process is performed after lamination of the inner layer substrate and the resin sheet, preheating may usually be performed after the smoothing process.

[0479] When a resin sheet is used, the method for manufacturing the circuit board may include a step of peeling off the support of the resin sheet after lamination of the inner layer substrate and the resin sheet. The peeling off of the support may be performed between step (I) and step (II), or after step (II). Furthermore, if the method for manufacturing the circuit board includes a step of forming holes in the insulating layer (III), a step of roughening the insulating layer (IV), and a step of forming a conductor layer (V), as described later, the peeling off of the support may be performed between step (II) and step (III), between step (III) and step (IV), or between step (IV) and step (V).

[0480] The method for manufacturing a circuit board may include a step (III) after step (II) in which holes such as via holes and through holes are formed in the insulating layer. The method for forming the holes can be selected according to factors such as the composition of the resin composition used to form the insulating layer. For example, holes may be formed by processing methods such as drilling, laser processing, and plasma processing, with laser processing being preferred. For example, holes may be formed by irradiating the insulating layer with laser light after peeling off the support, or by irradiating the insulating layer with laser light through the support. The dimensions and shape of the holes may be appropriately determined according to the design of the circuit board.

[0481] A method for manufacturing a circuit board may include a step (IV) of roughening the insulating layer. The roughening treatment can roughen the surface of the insulating layer. Furthermore, the roughening treatment can remove smear (resin residue) from the insulating layer. For this reason, this roughening treatment is sometimes called "desmear treatment". For example, if holes are formed in step (III), smear may be formed inside those holes, so it is preferable to perform the roughening treatment in step (IV) after step (III) to remove the aforementioned smear.

[0482] The procedure and conditions for the roughening treatment are not particularly limited, and known procedures and conditions commonly used when forming the insulating layer of a circuit board can be employed. For example, the roughening treatment may be carried out by a wet method in which the insulating layer is subjected to a dry method such as plasma, a swelling treatment with a swelling solution, an oxidation treatment with an oxidizing agent, and a neutralization treatment with a neutralizing solution in that order.

[0483] Examples of swelling solutions used for roughening treatment include alkaline solutions and surfactant solutions, with alkaline solutions being preferred. Sodium hydroxide solution and potassium hydroxide solution are more preferred as the alkaline solution. Examples of commercially available swelling solutions include "Swelling Dip Securigant P" and "Swelling Dip Securigant SBU" manufactured by Atotec Japan. Swelling treatment with a swelling solution can be carried out, for example, by immersing the insulating layer in a swelling solution at 30°C to 90°C for 1 to 20 minutes. From the viewpoint of suppressing the swelling of the resin of the insulating layer to an appropriate level, it is preferable to immerse the insulating layer in a swelling solution at 40°C to 80°C for 5 to 15 minutes.

[0484] Examples of oxidizing agents used in the roughening treatment include alkaline permanganate solutions obtained by dissolving potassium permanganate or sodium permanganate in an aqueous solution of sodium hydroxide. The oxidation treatment with an oxidizing agent such as an alkaline permanganate solution is preferably carried out by immersing the insulating layer in an oxidizing agent solution heated to 60°C to 100°C for 10 to 30 minutes. Furthermore, the concentration of permanganate in the alkaline permanganate solution is preferably 5% to 10% by mass. Examples of commercially available oxidizing agents include alkaline permanganate solutions such as "Concentrate Compact CP" and "Dosing Solution Securigans P" manufactured by Atotec Japan.

[0485] As the neutralizing solution used for roughening treatment, an acidic aqueous solution is preferred, and a commercially available example is "Reduction Solution Securigant P" manufactured by Attec Japan. Neutralization treatment with a neutralizing solution can be carried out by immersing the treated surface, which has been oxidized with an oxidizing agent, in a neutralizing solution at 30°C to 80°C for 5 to 30 minutes. From the viewpoint of workability, it is preferable to immerse the object that has been oxidized with an oxidizing agent in a neutralizing solution at 40°C to 70°C for 5 to 20 minutes.

[0486] Examples of dry desmear treatments include desmear treatment using plasma. In desmear treatment using plasma, the insulating layer is treated with plasma generated by introducing gas into a plasma generator to remove smear formed in the pores. There are no particular restrictions on the method of generating the plasma, and examples include microwave plasma generated by microwaves, high-frequency plasma generated by high-frequency, atmospheric pressure plasma generated under atmospheric pressure, and vacuum plasma generated under vacuum, with vacuum plasma generated under vacuum being preferred.

[0487] The gas species used in the dry desmear treatment (the gas species used to create plasma) is not particularly limited as long as it can remove the smear in the pores. For example, it is preferable to use a gas containing fluorine atoms, or a gas containing either N2 or O2. Examples of gases containing fluorine atoms include F2, CF4, C2F6, and SF6. In this case, in addition to a gas containing fluorine atoms, N2, or O2, other gases such as Ar may also be included. In particular, from the viewpoint of improving smear removal performance, it is preferable that the gas species contains a gas containing fluorine atoms, or any of N2 or O2, more preferably a gas containing a gas containing fluorine atoms and O2, even more preferably a mixed gas containing O2 and at least one of N2 and CF4, and especially preferably a mixed gas containing O2 and CF4.

[0488] When a mixed gas is used as the gas species, the mixing ratio (gas containing either N2 or O2 / other gas: unit is sccm) is preferably 1 / 0.01 to 1 / 100, more preferably 1 / 0.5 to 1 / 10, and even more preferably 1 / 1 to 1 / 5, from the viewpoint of improving smear removal performance.

[0489] The duration of the dry desmear treatment is not particularly limited, but is preferably 30 seconds or more, more preferably 60 seconds or more, 90 seconds or more, or 120 seconds or more. The upper limit of the duration of the dry desmear treatment is preferably 10 minutes or less, and more preferably 5 minutes or less, from the viewpoint of easily achieving an insulating layer with low surface roughness after the desmear treatment.

[0490] Dry desmearing can be performed using commercially available dry desmearing equipment. Among commercially available dry desmearing equipment, examples suitable for circuit board manufacturing include the plasma dry etching equipment from Oxford Instruments, the microwave plasma equipment from Nissin, and the atmospheric pressure plasma etching equipment from Sekisui Chemical Co., Ltd.

[0491] The method for manufacturing a circuit board may include a step (V) of forming a conductive layer on an insulating layer. If the method for manufacturing a circuit board includes step (III) or (IV), the step of forming the conductive layer (V) is usually preferably performed after steps (III) and (IV).

[0492] The conductive material used in the conductive layer is not particularly limited. In a preferred embodiment, the conductive layer contains one or more metals selected from the group consisting of gold, platinum, palladium, silver, copper, aluminum, cobalt, chromium, zinc, nickel, titanium, tungsten, iron, tin, and indium. The conductive layer may be a single-metal layer or an alloy layer. Examples of alloy layers include layers formed from alloys of two or more metals selected from the above group (e.g., nickel-chromium alloy, copper-nickel alloy, and copper-titanium alloy). Among these, single-metal layers of chromium, nickel, titanium, aluminum, zinc, gold, palladium, silver, or copper, or alloy layers of nickel-chromium alloy, copper-nickel alloy, or copper-titanium alloy are preferred from the viewpoint of versatility in conductive layer formation, cost, and ease of patterning, more preferred are single-metal layers of chromium, nickel, titanium, aluminum, zinc, gold, palladium, silver, or copper, more preferred are single-metal layers of chromium, nickel, titanium, aluminum, zinc, gold, palladium, silver, or copper, and even more preferred are single-metal layers of nickel-chromium alloy, with single-metal layers of copper being even more preferred.

[0493] The conductive layer may have a single-layer structure, or it may have a multi-layer structure including two or more single-metal layers or alloy layers made of different types of metals or alloys. When the conductive layer has a multi-layer structure, the layer in contact with the insulating layer is preferably a single-metal layer of chromium, zinc, or titanium, or an alloy layer of nickel-chromium alloy.

[0494] The thickness of the conductor layer depends on the design of the circuit board, but is preferably 3 μm to 35 μm, and more preferably 5 μm to 30 μm.

[0495] The conductor layer may be formed by plating. For example, a conductor layer having a desired wiring pattern can be formed by plating the surface of the insulating layer using conventionally known techniques such as the semi-additive method or the fully additive method. From the viewpoint of ease of manufacture, the semi-additive method is preferred. An example of forming the conductor layer by the semi-additive method is shown below.

[0496] First, an electroless plating layer (plating seed layer) is formed on the surface of the insulating layer by electroless plating. Next, a mask pattern is formed on the formed electroless plating layer, exposing a portion of the electroless plating layer corresponding to the desired wiring pattern. After forming an electroplating layer on the exposed electroless plating layer by electroplating, the mask pattern is removed. Subsequently, the unnecessary electroless plating layer can be removed by etching to form a conductor layer having the desired wiring pattern.

[0497] As another example, the conductor layer may be formed using metal foil. When forming the conductor layer using metal foil, step (V) is preferably performed between steps (I) and (II). For example, after step (I), the support is removed and the metal foil is laminated onto the surface of the exposed resin composition layer. The lamination of the resin composition layer and the metal foil may be carried out by a vacuum lamination method. The lamination conditions may be the same as those described for step (I). Next, step (II) is performed to form an insulating layer. Subsequently, using the metal foil on the insulating layer, a conductor layer having a desired wiring pattern can be formed by known techniques such as the subtractive method or the modified semi-additive method. The metal foil can be manufactured by known methods such as the electrolytic method or the rolling method. Examples of commercially available metal foils include HLP foil and JXUT-III foil from JX Metals, and 3EC-III foil and TP-III foil from Mitsui Mining & Smelting Co., Ltd.

[0498] When a conductive layer is formed on an insulating layer, the method for manufacturing the circuit board may include annealing after the formation of the conductive layer. Annealing can improve the adhesion between the insulating layer and the conductive layer. Annealing can be performed, for example, by heating at 150°C to 210°C for 20 to 180 minutes.

[0499] In another embodiment, the conductive layer may be formed by sputtering. When forming the conductive layer by sputtering, typically a conductive seed layer is formed on the insulating layer by sputtering, and then a conductive sputtered layer is formed on the conductive seed layer by further sputtering. Alternatively, the surface of the insulating layer may be cleaned by reverse sputtering before forming the conductive seed layer by sputtering. Preferred gases for reverse sputtering are Ar gas, O2 gas, and N2 gas. If the conductive seed layer is Cu and Cu alloy, Ar gas, O2 gas, or a mixture of Ar and O2 gas is preferred. If the conductive seed layer is Ti, Ar gas, N2 gas, or a mixture of Ar and N2 gas is preferred. Furthermore, if the seed layer is Cr and Cr alloy (such as nichrome), Ar gas, O2 gas, or a mixture of Ar and O2 gas is preferred. Sputtering can be performed using various sputtering devices such as magnetron sputtering and mirrortron sputtering. Examples of metals used to form the conductive seed layer include Cr, Ni, Ti, and nichrome. Cr and Ti are particularly preferred. The thickness of the conductive seed layer is preferably 5 nm or more, more preferably 10 nm or more, preferably 1000 nm or less, and more preferably 500 nm or less. Examples of metals that form the conductive sputtered layer include Cu, Pt, Au, Pd, etc. Cu is particularly preferred. The thickness of the conductive sputtered layer is preferably 50 nm or more, more preferably 100 nm or more, preferably 3000 nm or less, and more preferably 1000 nm or less.

[0500] In the method for manufacturing a circuit board, each of the above-described steps may be performed only once or repeated two or more times. For example, steps (I) to (V) may be repeatedly performed to form a circuit board having a multilayer structure, such as a multilayer printed wiring board, which comprises multiple insulating layers and conductive layers.

[0501] The method for manufacturing a circuit board may include any additional steps in addition to the steps described above. For example, the method for manufacturing a circuit board may include a step of providing a semiconductor chip so as to be bonded to a conductor layer. Specifically, when manufacturing a circuit board for a semiconductor chip package that includes a semiconductor chip, the method for manufacturing the circuit board may include a step of providing the semiconductor chip. The conditions for providing the semiconductor chip can be appropriate conditions that allow the terminal electrodes of the semiconductor chip and the conductor layer formed on the insulating layer to be conductively connected. For example, conditions used in flip-chip mounting may be used. The semiconductor chip may also be bonded via an insulating adhesive or by reflow soldering. Furthermore, if necessary, the provided semiconductor chip may be filled with mold underfill material. The method for manufacturing a circuit board may also include, for example, a step of forming a sealing layer, a step of forming a solder resist layer, and a step of dicing the manufactured circuit board into individual pieces.

[0502] Examples of circuit boards include printed circuit boards and semiconductor chip packages. Examples of semiconductor chip packages include FC-CSP, MIS-BGA packages, ETS-BGA packages, fan-out type WLP (Wafer Level Package), fan-in type WLP, fan-out type PLP (Panel Level Package), and fan-in type PLP. In these semiconductor chip packages, it is preferable to form a rewiring layer as an insulating layer using a cured product obtained by curing the above-mentioned resin composition. However, the circuit boards are not limited to those exemplified herein.

[0503] <Semiconductor device> The aforementioned circuit board can be used in the manufacture of semiconductor devices. The semiconductor device comprises the aforementioned circuit board. Examples of semiconductor devices include various types of semiconductor devices used in electrical products (e.g., computers, mobile phones, smartphones, tablet devices, wearable devices, digital cameras, medical equipment, and televisions, etc.) and vehicles (e.g., motorcycles, automobiles, trains, ships, and aircraft, etc.). [Examples]

[0504] The present invention will be specifically described below with reference to examples. However, the present invention is not limited to the following examples. In the following explanation, "parts" and "%" refer to "parts by mass" and "% by mass," respectively, unless otherwise specified. Unless otherwise specified, the temperature and pressure conditions were room temperature (23°C) and atmospheric pressure (1 atm). <Synthesis Example 1: Synthesis of Maleimide Resin C-1> A MEK solution (62% by mass of non-volatile components) of maleimide resin C-1, represented by the following formula and synthesized by the method described in Synthesis Example 1 of the Japan Institute of Invention and Innovation, Technical Report No. 2020-500211, was prepared. The Mw / Mn ratio of this maleimide resin C-1 was 1.81, and the value of t'' in the following formula was 1.47 (mainly 1, 2, or 3).

[0505] [ka]

[0506] <Synthesis Example 2: Synthesis of Maleimide Resin C-2> (I) Synthesis of intermediate amine compound C'-2 In a flask equipped with a thermometer, condenser, Dean-Stark trap, and stirrer, 242.4 g (2.0 mol) of 2-ethylaniline, 242 g of xylene, and 80 g of activated clay were charged. The mixture was heated to 130°C while stirring and held for 30 minutes. Then, 272.0 g of DVB-810 (a mixture of divinylbenzene / ethylstyrene (divinylbenzene / ethylstyrene = 81 / 19 (mol)%), manufactured by Nippon Steel Chemical & Material) was added dropwise over 2 hours, and the mixture was allowed to react for 1 hour. After that, the mixture was heated to 190°C over 6 hours and held for 10 hours. After holding, the mixture was air-cooled to 100°C, diluted with 300 g of toluene, the activated clay was removed by filtration, and the solvent and other low molecular weight substances such as unreacted materials were removed under reduced pressure to obtain the intermediate amine compound C'-2. The amine equivalent of the intermediate amine compound C'-2 was 214 g / equivalent.

[0507] (II) Synthesis of maleimide resin C-2 (maleimidization) A 2L flask equipped with a thermometer, condenser, Dean-Stark trap, and stirrer was charged with 117.7g (1.2mol) maleic anhydride and 700g toluene, and stirred at room temperature. Next, a mixed solution of 214g (1 equivalent) of the intermediate amine compound C'-2 and 175g of dimethylformamide was added dropwise over 1 hour, and the mixture was allowed to react for 2 hours. 37.1g of p-toluenesulfonic acid monohydrate was added to the reaction solution, and the mixture was heated to 115°C. The azeotropic formation of water and toluene under reflux was cooled and separated, and only toluene was returned to the system for dehydration over 5 hours. After air cooling to room temperature, the mixture was neutralized with 49% NaOH. Subsequently, toluene and water were removed by vacuum distillation at 60°C, and 600g of MEK (methyl ethyl ketone) was added to the DMF solution remaining in the flask. The solution was heated to 60°C, and the salts in the solution were removed by three separatory treatments with 200g of deionized water. Sodium sulfate was added, and after drying, the reaction product was concentrated under reduced pressure and vacuum-dried at 80°C to obtain maleimide resin C-2.

[0508] <Synthesis Example 3: Synthesis of Maleimide Resin C-3> (I) Synthesis of intermediate amine compound C'-3 In a flask equipped with a thermometer, condenser, Dean-Stark trap, and stirrer, 400 g (3.3 mol) of 2-ethylaniline, 127 g of a compound having a benzyl ether skeleton (Fudo Co., Ltd. "Nikanol L"), 193 g of toluene, and 53 g of activated clay were charged. The mixture was heated to 120°C while stirring and held for 30 minutes. Then, the temperature was raised to 150°C and held for 3 hours. After holding, the temperature was raised to 200°C over 30 minutes and held for 10 hours. After holding, the mixture was diluted with 193 g of toluene, the activated clay was removed by filtration, and the solvent and low molecular weight substances such as unreacted materials were removed by distillation under reduced pressure to obtain intermediate amine compound B'-3. The amine equivalent of intermediate amine compound C'-3 was 209 g / eq.

[0509] (II) Synthesis of maleimide resin C-3 (maleimidization) A 2L flask equipped with a thermometer, condenser, Dean-Stark trap, and stirrer was charged with 73.2g (126mol, 1.3 equivalents) of maleic anhydride and 461g of toluene, and stirred at room temperature. Next, a mixed solution of 209g (1 equivalent) of the intermediate amine compound C'-3 and 57.7g of dimethylformamide was added dropwise over 1 hour, and the reaction was allowed to proceed for 2 hours. 9.72g of p-toluenesulfonic acid monohydrate was added to the reaction mixture, and the mixture was heated under reflux. The azeotropic formation of water and toluene was cooled and separated. After heating to 115°C and cooling the azeotropic formation of water and toluene under reflux, only the toluene was returned to the system and the dehydration reaction was carried out for 5 hours. After air cooling to room temperature, the brown solution was concentrated under reduced pressure and dissolved in 600 g of ethyl acetate. The mixture was washed three times with 200 g of deionized water and three times with 150 g of 2% by mass sodium bicarbonate aqueous solution. Sodium sulfate was added, the mixture was dried, and the reaction product was concentrated under reduced pressure. The resulting product was vacuum-dried at 80°C for 4 hours to obtain a product containing maleimide resin C-3 (a solution with 62% by mass of nonvolatile components). In the following formula, n was composed of 1, 2, or 3, and n1' was 1.

[0510] [ka]

[0511] <Synthesis Example 4: Synthesis of Vinyl Resin D1> In a flask equipped with a stirring device, 2,2-bis(4-hydroxy-3-methylphenyl)propane (64.09 g), 4,6-dichloro-2-phenylpyrimidine (41.43 g), and potassium carbonate (46.65 g) were weighed in, and N-methyl-2-pyrrolidone (113.92 g) was added. The mixture was reacted at 130°C for 6 hours under a nitrogen atmosphere. After the reaction, the container was cooled to 10°C, chloromethylstyrene (27.95 g) was added dropwise, and the mixture was reacted at 65°C for 6 hours.

[0512] The reaction solution was diluted by adding N-methyl-2-pyrrolidone (258.1 g). The salt was removed from the diluted reaction solution by filtration. The solution from which the salt had been removed was added to methanol (4960 g). The precipitated solid was filtered off, washed with a small amount of methanol, and recovered by filtering again. The recovered solid was dried under reduced pressure at 80°C for 12 hours using a vacuum dryer to obtain vinyl resin D1 represented by the following formula (yield 100.40 g, yield 92%). The weight-average molecular weight (Mw) of vinyl resin D1 was 3,300. Vinyl resin D1 is the vinyl resin corresponding to component (D-1). In the following formula, nd1 was between 0 and 5.

[0513] [ka]

[0514] <Synthesis Example 5: Synthesis of Vinyl Resin D2> The synthesis was carried out in the same procedure as in Synthesis Example 4, except that the raw materials and alkali metal compounds used were changed to 2,2-bis(4-hydroxy-3-methylphenyl)propane (64.09 g), 4,6-dichloro-2-phenylpyrimidine (31.08 g), 4,6-dichloropyrimidine (6.86 g), potassium carbonate (46.65 g), and chloromethylstyrene (22.01 g). By this operation, vinyl resin D2 represented by the following formula was obtained (93.06 g, yield 89%). The weight-average molecular weight (Mw) of vinyl resin D-2 was 3,100. Vinyl resin D2 is the vinyl resin corresponding to component (D-1). In the following formula, nd2 was between 0 and 5. md2 was between 0 and 5.

[0515] [ka]

[0516] <Synthesis Example 6: Synthesis of Vinyl Resin D3> In a flask equipped with a stirring device, 1,1-bis(4-hydroxy-3-methylphenyl)-3,3,5-trimethylcyclohexane (33.85 g), 4,6-dichloro-2-phenylpyrimidine (16.66 g), and potassium carbonate (18.66 g) were weighed in, and N-methyl-2-pyrrolidone (42.50 g) was added. The mixture was reacted at 100°C for 6 hours under a nitrogen atmosphere. After the reaction, the container was cooled to 10°C, and chloromethylstyrene (8.680 g) was added dropwise, followed by reaction at 100°C for 4 hours.

[0517] The reaction solution was diluted by adding N-methyl-2-pyrrolidone (42.50 g). The salt was removed from the diluted reaction solution by filtration. The salt-free solution was added to methanol (6900 g). The precipitated solid was filtered off, washed with a small amount of methanol, and recovered by filtering again. The recovered solid was dried under reduced pressure at 60°C for 12 hours using a vacuum dryer to obtain vinyl resin D3 represented by the following formula (yield 44.10 g, yield 90%). The weight-average molecular weight (Mw) of compound D3 was 3,400. Vinyl resin D3 is the vinyl resin corresponding to component (D-1). In the following formula, nd3 was between 0 and 5.

[0518] [ka]

[0519] <Synthesis Example 7: Synthesis of Vinyl Resin D4> The synthesis was carried out in the same procedure as in Synthesis Example 6, except that the raw materials and alkali metal compounds used were changed to 2,2-bis(4-hydroxy-3-methylphenyl)propane (25.63 g), 9,9-bis(4-hydroxy-3-methylphenyl)fluorene (37.84 g), 4,6-dichloro-2-phenylpyrimidine (33.31 g), chloromethylstyrene (17.36 g), potassium carbonate (37.31 g), and N-methyl-2-pyrrolidone (181.4 g). By this operation, vinyl resin D4 represented by the following formula was obtained (yield 89.30 g, yield 90%). The weight-average molecular weight (Mw) of vinyl resin D4 was 4,000. In the following formula, nd4 was between 0 and 5.

[0520] [ka]

[0521] (In the formula, R X This indicates a divalent group represented by the following formula (X-1) or a divalent group represented by the following formula (X-2). In formulas (X-1) and (X-2), the dashed line indicates the bonding site. Vinyl resin D4 is a vinyl resin corresponding to component (D-1).

[0522] [ka]

[0523] <Synthesis Example 8: Synthesis of Vinyl Resin D5> The synthesis was carried out in the same procedure as in Synthesis Example 4, except that the raw materials and alkali metal compounds used were changed to 2,2-bis(4-hydroxy-3-methylphenyl)propane (51.27 g), 4,4'-(2-hydroxybenzylidene)bis(2,3,6-trimethylphenol) (18.78 g), 4,6-dichloro-2-phenylpyrimidine (41.43 g), potassium carbonate (51.31 g), and chloromethylstyrene (38.55 g). By this operation, vinyl resin D5 having structural units represented by the following formulas (d5-1) and (d5-2) was obtained (yield 108.17 g, yield 89%). Vinyl resin D5 contains vinylbenzyl groups at its termini. The weight-average molecular weight (Mw) of vinyl resin D5 was 4,200. Vinyl resin D5 is the vinyl resin corresponding to component (D-2).

[0524] [ka]

[0525] (In equations (d5-1) and (d5-2), ◆ indicates that it is combined with any of ◆◆.)

[0526] <Synthesis Example 9: Synthesis of Vinyl Resin D6> The synthesis was carried out in the same procedure as in Synthesis Example 4, except that the raw materials and alkali metal compounds used were changed to 2,2-bis(4-hydroxy-3-methylphenyl)propane (57.68 g), 1,1,1-tris(2-methyl-4-hydroxy-5-tert-butylphenyl)butane (13.62 g), 4,6-dichloro-2-phenylpyrimidine (41.43 g), potassium carbonate (48.98 g), and chloromethylstyrene (33.25 g). By this operation, vinyl resin D6 having structural units represented by the following formulas (d6-1) and (d6-2) was obtained (yield 110.00 g, yield 92%). Vinyl resin D6 contains vinylbenzyl groups at its termini. The weight-average molecular weight (Mw) of vinyl resin D6 was 4,100. Vinyl resin D6 is the vinyl resin corresponding to component (D-2).

[0527] [ka]

[0528] (In equations (d6-1) and (d6-2), ◆ indicates that it is combined with any of ◆◆.)

[0529] <Synthesis Example 10: Synthesis of Vinyl Resin D7> The synthesis was carried out in the same procedure as in Synthesis Example 4, except that the raw materials and alkali metal compounds used were changed to 2,2-bis(4-hydroxy-3-methylphenyl)propane (51.27 g), 4,4',4'',4'''-(propane-2,2-diylbis(cyclohexane-4,1,1-triyl)tetrakis(2-methylphenol) (31.63 g), 4,6-dichloro-2-phenylpyrimidine (41.43 g), potassium carbonate (55.98 g), and chloromethylstyrene (49.15 g). By this operation, vinyl resin D7 having structural units represented by the following formulas (d7-1) and (d7-2) was obtained (yield 133.27 g, yield 88%). The weight-average molecular weight (Mw) of vinyl resin D7 was 17,900. Vinyl resin D7 is the vinyl resin corresponding to component (D-2).

[0530] [ka]

[0531] (In equations (d7-1) and (d7-2), ◆ indicates that it is combined with any of ◆◆.)

[0532] <Synthesis Example 11. Thermoplastic Resin: Synthesis of Polyimide Resin H> A monomer composition was obtained by mixing 46.5 g of 2,2-bis[4-(3,4-dicarboxyphenoxy)phenyl]propane dianhydride (BPADA), 37.8 g of 4,4'-[1,4-phenylenebis[(1-methylethylidene)-4,1-phenyleneoxy]]bisbenzeneamine (BPPAN), 12.8 g of dimeramine (PRIAMINE1075, manufactured by Croda Japan), 1.9 g of 5-norbornene-2,3-dicarboxylic acid anhydride, and 40 g of toluene as a solvent in 400 g of N,N-dimethylacetamide (DMAc) as a solvent. The mixture was stirred and reacted at room temperature and atmospheric pressure for 3 hours. This yielded a polyamic acid solution.

[0533] Next, the polyamic acid solution was heated, and while maintaining the temperature at approximately 160°C, the condensed water was azeotropically removed with toluene under a nitrogen stream. It was confirmed that a predetermined amount of water had accumulated in the moisture meter and that no further water leakage was observed. After confirmation, the reaction solution was further heated and stirred at 200°C for 1 hour. After that, it was cooled. This yielded a varnish containing terminally olefin-modified polyimide resin H (20% by mass of non-volatile components).

[0534] [Examples 1-40, Comparative Examples 1-2] <Preparation of resin composition> Each component was weighed in the mass parts listed in Tables 1 and 2 and uniformly dispersed using a high-speed rotary mixer to obtain a resin composition (resin varnish).

[0535] <Manufacturing of resin sheets> As a support, we prepared a polyethylene terephthalate film (Toray Industries, Ltd.'s "Lumirror R80," 38 μm thick, softening point 130°C) that had been treated with an alkyd resin-based release agent (Lintec Corporation's "AL-5"). On the support, the resin compositions obtained in Examples 1 to 40 and Comparative Examples 1 to 2 were uniformly applied using a die coater so that the thickness of the dried resin composition layer was 40 μm, and the resin composition layer was formed on the support by drying at 90°C for 3 minutes. Next, a rough surface of a polypropylene film (Alfan MA-411, manufactured by Oji F-Tex Co., Ltd., 15 μm thick) was laminated as a protective film to the side of the resin composition layer that was not bonded to the support. This resulted in a resin sheet having the support, resin composition layer, and protective film in that order.

[0536] <Test Example 1: Measurement of Dielectric Properties (Dielectric Constant, Dielectric Loss Tangent) (Curing under Air Atmosphere)> The protective film was peeled off the resin sheets prepared in Examples 1-40 and Comparative Examples 1-2, and the resin composition layer was heat-cured by heating at 200°C for 90 minutes in an air atmosphere. The support was then peeled off. The resulting cured material was cut into pieces 2 mm wide and 80 mm long to be used as test specimens for evaluation. For each test specimen, the dielectric constant and dielectric loss tangent were measured using the cavity resonance perturbation method with an Agilent Technologies HP8362B at a measurement frequency of 5.8 GHz and a measurement temperature of 23°C. Measurements were performed on three test specimens, and the average values ​​were calculated. In the table, the dielectric loss tangent of the obtained cured material is indicated as Dielectric Loss Tangent (Air).

[0537] <Test Example 2: Measurement of Dielectric Properties (Dielectric Constant, Dielectric Loss Tangent) (Curing under Nitrogen Atmosphere)> The protective film was peeled off the resin sheets prepared in the examples and comparative examples, and the resin composition layer was heat-cured by heating at 200°C for 90 minutes under a nitrogen atmosphere. The support was then peeled off. The resulting cured material was cut into pieces 2 mm wide and 80 mm long to be used as test specimens for evaluation. For each test specimen, the dielectric constant and dielectric loss tangent were measured using the cavity resonance perturbation method with an Agilent Technologies HP8362B at a measurement frequency of 5.8 GHz and a measurement temperature of 23°C. Measurements were performed on three test specimens, and the average values ​​were calculated. In the table, the dielectric loss tangent of the obtained cured material is shown as dielectric loss tangent (N2).

[0538] <Test Example 3: Calculation of Dielectric Loss Tangent (N2 / Air)> From the dielectric loss tangent values ​​obtained in Test Example 2 and Test Example 1, the dielectric loss tangent (Air) and dielectric loss tangent (N2) were used to calculate the relative dielectric loss tangent (N2 / Air) = dielectric loss tangent (N2) / dielectric loss tangent (Air).

[0539] <Test Example 4: Evaluation of Crack Resistance> (1) Preparation of the substrate for crack evaluation For crack evaluation, a core material (Resonac Corporation's "E705GR", 400 μm thick) was used, which consisted of a thermally setting resin and an inorganic filler impregnated adhesive sheet with a lattice pattern of circular copper pads (35 μm thick) with a diameter of 350 μm and a copper thickness of 35 μm, spaced 400 μm apart, to achieve a copper content of 60%.

[0540] (2) Lamination of resin sheets Using a batch-type vacuum pressure laminator (Nikko Materials Co., Ltd. 2-stage build-up laminator "CVP700"), resin sheets obtained in the examples and comparative examples (resin composition layer thickness: 30 μm) were laminated to both sides of the crack evaluation substrate so that the resin composition layer was bonded to the crack evaluation substrate. Lamination was performed by reducing the pressure to 13 hPa or less for 30 seconds, and then pressing at 100°C and a pressure of 0.74 MPa for 30 seconds.

[0541] (3) Thermocuring of the resin composition layer Subsequently, the crack evaluation substrate laminated with a resin sheet was placed in a 100°C oven and heated for 30 minutes, then transferred to a 190°C oven and heated for another 30 minutes to heat-cur the resin composition layer and form an insulating layer. After that, the support was peeled off to obtain a cured substrate A having an insulating layer, an inner layer substrate, and another insulating layer in that order.

[0542] (4) Roughening treatment A desmear treatment was performed on the cured substrate A as a roughening treatment. The following wet desmear treatment was carried out. (Wet desmear treatment) Cured substrate A was immersed in a swelling solution (Atotec Japan's "Swelling Dip Securigant P," an aqueous solution of diethylene glycol monobutyl ether and sodium hydroxide) at 60°C for 5 minutes, then immersed in an oxidizing agent solution (Atotec Japan's "Concentrate Compact CP," an aqueous solution with approximately 6% potassium permanganate and approximately 4% sodium hydroxide) at 80°C for 15 minutes, then immersed in a neutralizing solution (Atotec Japan's "Reduction Solution Securigant P," an aqueous sulfuric acid solution) at 40°C for 5 minutes, and finally dried at 80°C for 15 minutes. This substrate is referred to as "Evaluation Substrate A."

[0543] (5) Crack evaluation One hundred copper pads from evaluation substrates obtained after roughening were observed to check for cracks in the resin composition layer, and evaluated according to the following criteria. ○: Fewer than 10 cracks △: 10 to less than 20 cracks ×: More than 20 cracks

[0544] <Test Example 5: Evaluation of Substrate Adhesion> (1) Lamination of resin sheet A onto the inner layer substrate As the inner layer substrate, a glass cloth substrate epoxy resin double-sided copper-clad laminate with copper foil on the surface (copper foil thickness 18 μm, substrate thickness 0.8 mm, Panasonic "R1515A") was prepared. The copper foil on this surface was roughened by etching with a micro-etching agent (MEC "CZ8101") to a copper etching amount of 1 μm. The resin sheet A obtained above was laminated on both sides of the inner layer substrate using a batch-type vacuum pressure laminator (Nikko Materials Co., Ltd., 2-stage build-up laminator "CVP700") so that the resin composition layer of resin sheet A was in contact with the inner layer substrate. Lamination was performed by reducing the pressure to 13 hPa or less for 30 seconds, followed by pressing at a temperature of 100°C and a pressure of 0.74 MPa for 30 seconds. Next, the laminated resin sheet A was heat-pressed at atmospheric pressure, 100°C, and a pressure of 0.5 MPa for 60 seconds to smooth it out. After that, the support was peeled off to obtain an "intermediate multilayer body I" containing a resin composition layer / inner substrate / resin composition layer in that order.

[0545] (2) Lamination of copper foil A copper foil with a glossy surface (35 μm thick, manufactured by Mitsui Mining & Smelting Co., Ltd., "3EC-III") was prepared. The glossy surface of this copper foil was roughened by etching with a micro-etching agent (manufactured by MEC Corporation, "CZ8401") to a copper etching depth of 0.1 μm. The copper foil obtained in this way is called "roughened copper foil". This roughened copper foil was laminated on both sides of the intermediate multilayer I such that the roughened surface of the roughened copper foil was bonded to the resin composition layer of the intermediate multilayer I. This lamination was carried out under the same conditions as the lamination of resin sheet A to the inner substrate described above. As a result, an "intermediate multilayer II" was obtained, containing roughened copper foil / resin composition layer / inner substrate / resin composition layer / roughened copper foil in this order.

[0546] (3) Thermocuring of the resin composition layer The obtained intermediate multilayer II was placed in a 100°C oven and heated for 30 minutes, then transferred to a 190°C oven and heated for another 30 minutes. Next, the intermediate multilayer II was removed from the oven and left in a room temperature atmosphere, and then placed in a 200°C oven and heated for an additional 90 minutes. This caused the resin composition layer to heat-cur, resulting in an "evaluation substrate" containing, in this order, roughened copper foil / insulating layer as a cured product of the resin composition layer / inner layer substrate / insulating layer as a cured product of the resin composition layer / roughened copper foil. In this evaluation substrate, the roughened copper foil corresponds to the conductive layer.

[0547] (4) Measurement of adhesion strength with the conductor layer (CZ copper peel strength) Using the obtained evaluation substrate, the peel strength between the roughened copper foil and the insulating layer was measured. This peel strength measurement was performed in accordance with JIS C6481. Specifically, the peel strength was measured by the following procedure. A rectangular section measuring 10 mm wide and 100 mm long was cut into the roughened copper foil of the evaluation substrate. One end of this rectangular section was peeled off and grasped with a gripper (TSE Corporation's Autocom type testing machine "AC-50C-SL"). A 35 mm section of this rectangular area was peeled vertically, and the load (kgf / cm) during this peeling was measured as the peel strength. The above peeling was performed at a speed of 50 mm / min at room temperature.

[0548] <Test Example 6: Evaluation of Plating Penetration> (1) Preparation of the inner layer substrate As the inner layer substrate, a glass cloth substrate epoxy resin double-sided copper-clad laminate (copper foil thickness 18 μm, substrate thickness 0.8 mm, Panasonic "R1515A") on which the inner layer circuit was formed was etched to a thickness of 1 μm on both sides with a micro-etching agent (MEC "CZ8101") to roughen the copper surface.

[0549] (2) Lamination of resin sheets The protective film was peeled off the resin sheet to expose the resin composition layer. Using a batch-type vacuum pressure laminator (Nikko Materials Co., Ltd., 2-stage build-up laminator "CVP700"), the resin composition layer was laminated to both sides of the inner layer substrate so that it was in contact with the inner layer substrate. Lamination was performed by reducing the pressure to 13 hPa or less by depressurizing for 30 seconds, and then pressing at 100°C and a pressure of 0.74 MPa for 30 seconds. Subsequently, a heat press was performed at 100°C and a pressure of 0.5 MPa for 60 seconds.

[0550] (3) Thermocuring of the resin composition layer Subsequently, the inner layer substrate laminated with a resin sheet was placed in a 100°C oven and heated for 30 minutes, then transferred to a 190°C oven and heated for another 30 minutes to heat-cur the resin composition layer and form an insulating layer. After that, the support was peeled off to obtain a cured substrate B having the insulating layer, inner layer substrate, and insulating layer in that order.

[0551] (4) Roughening treatment Desmear treatment was performed on the cured substrate B as a roughening treatment. The following wet desmear treatment was performed (wet desmear treatment). Cured substrate B was immersed in a swelling solution (Atotec Japan's "Swelling Dip Securigant P," an aqueous solution of diethylene glycol monobutyl ether and sodium hydroxide) at 60°C for 5 minutes, then immersed in an oxidizing agent solution (Atotec Japan's "Concentrate Compact CP," an aqueous solution with approximately 6% potassium permanganate and approximately 4% sodium hydroxide) at 80°C for 15 minutes, then immersed in a neutralizing solution (Atotec Japan's "Reduction Solution Securigant P," an aqueous sulfuric acid solution) at 40°C for 5 minutes, and finally dried at 80°C for 15 minutes. This substrate is referred to as "Evaluation Substrate B."

[0552] (5) Formation of electroless plating layer An electroless plating layer was formed on the roughened surface of the insulating layer according to the semi-additive method. Specifically, the substrate after roughening was immersed in an electroless plating solution containing PdCl2 at 40°C for 5 minutes, and then immersed in an electroless copper plating solution at 25°C for 20 minutes. Next, it was annealed by heating at 150°C for 30 minutes. The thickness of the formed electroless copper plating layer was 1 μm.

[0553] (6) Preparation of cross-sectional samples A scanning electron microscope (SMI3050SE focused ion beam / scanning ion microscope manufactured by SII Nanotechnology Inc.) was used to observe the cross-sectional sample and obtain an SEM image of the cross-section of the hardened body in a direction perpendicular to the first main surface.

[0554] (7) Evaluation of plating penetration The SEM image of the interface between the copper plating layer and the resin composition layer in the resin composition layer with a copper plating layer laminated on its upper surface, obtained in (6), was observed at a magnification of 3700x. During observation, the resin composition layer with the copper plating layer laminated on its upper surface was positioned with the copper plating layer on top and the resin composition layer on the bottom, and the interface between the copper plating layer and the resin composition layer was horizontal. In the obtained microscope image with a width of 24 μm, line L1 was defined as a line that is in contact with the uppermost resin composition layer in the microscope image and parallel to the interface between the copper plating layer and the resin composition layer. In the obtained microscope image with a width of 24 μm, line L2 was defined as a line that is in contact with the lowermost copper plating in the microscope image and parallel to the interface between the copper plating layer and the resin composition layer. The distance between line L1 and line L2 was defined as the plating penetration depth. Note that the smaller the plating penetration depth, the more effectively short circuits between wiring can be suppressed.

[0555] The compounds used in the examples and comparative examples are as follows: <(A) Ingredient: TEMPO> • 4-BenzoyloxyTEMPO: An organic free radical represented by the following formula (manufactured by Seiko Chemical Co., Ltd.) [ka] • BisTEMPO sebacate: An organic free radical represented by the following formula (manufactured by Seiko Chemical Co., Ltd.) [ka] • 4-MCTEMPO: An organic free radical represented by the following formula (manufactured by Seiko Chemical Co., Ltd.) [ka]

[0556] <(B) Component: Inorganic filler> • SO-C2: Spherical silica (manufactured by Admatex, average particle size 0.5 μm, specific surface area 5.8 m²) 2 ( / g) is surface-treated with a silane coupling agent (Shin-Etsu Chemical Co., Ltd. "KBM-573") before use. • SO-C4: Spherical silica (manufactured by Admatex, average particle size 1.0 μm, specific surface area 5.8 m²) 2 ( / g) is surface-treated with a silane coupling agent (Shin-Etsu Chemical Co., Ltd. "KBM-573") before use. • LHP-208: Spherical hollow silica (manufactured by Ube Eximo Co., Ltd., average particle size 0.5 μm, porosity 50 vol%) is surface-treated with a silane coupling agent (Shin-Etsu Chemical Co., Ltd. "KBM-573") and used. • MGH-005: Hollow aluminosilicate particles (average particle size 1.6 μm, porosity 80% by volume, manufactured by Taiheiyo Cement Corporation) are surface-treated with a silane coupling agent (Shin-Etsu Chemical Co., Ltd. "KBM-573"). ·UFP-30: Spherical silica (manufactured by Denka, average particle size 0.3μm, specific surface area 30m 2 ( / g) is surface-treated with a silane coupling agent (Shin-Etsu Chemical Co., Ltd. "KBM-573") before use.

[0557] <(C) Component: Maleimide resin> • MIR-3000-70MT: Aromatic maleimide resin (manufactured by Nippon Kayaku Co., Ltd., MEK / toluene mixed solution with 70% non-volatile component content) • MIR-5000-60T: Aromatic maleimide resin (manufactured by Nippon Kayaku Co., Ltd., toluene mixed solution with 60% non-volatile components) (A) Compounds containing specific structural units and specific terminal groups • "Synthesis Example 1": Maleimide resin C-1 obtained in Synthesis Example 1 • "Synthesis Example 2": Maleimide resin C-2 obtained in Synthesis Example 2 • "Synthesis Example 3": Maleimide resin C-3 obtained in Synthesis Example 3 • BMI689: Aliphatic maleimide resin (manufactured by Designer Molecules, an N-alkyl bismaleimide with a dimer amine-derived skeleton) • BMI1500: Aliphatic maleimide resin (manufactured by Designer Molecules, an N-alkyl bismaleimide with a dimer amine-derived skeleton)

[0558] <(D) Component: Vinyl resin> "Synthesis Example 4": Vinyl resin D1 obtained in Synthesis Example 4 "Synthesis Example 5": Vinyl resin D2 obtained in Synthesis Example 5 "Synthesis Example 6": Vinyl resin D3 obtained in Synthesis Example 6 "Synthesis Example 7": Vinyl resin D4 obtained in Synthesis Example 7 "Synthesis Example 8": Vinyl resin D5 obtained in Synthesis Example 8 "Synthesis Example 9": Vinyl resin D6 obtained in Synthesis Example 9 "Synthesis Example 10": Vinyl resin D7 obtained in Synthesis Example 10 "Vinyl Resin D8": A toluene solution of vinyl resin D8 represented by the following formula (70% by mass of non-volatile content). The active ester group equivalent of vinyl resin D8 is 248 g / eq. In the following formula, nd8 and md8 are 0 or greater. Vinyl resin D8 is the vinyl resin corresponding to component (D-3). [ka] • SA9000-111: Methacrylic-modified polyphenylene ether resin (manufactured by SABIC)

[0559] <(E) Ingredient: Curing accelerator> • 1B2PZ: Imidazole-based curing accelerator (manufactured by Shikoku Chemicals Co., Ltd.) • BT-120: Benzotriazole-based curing accelerator (manufactured by Johoku Chemical Co., Ltd.) • 5-Benzyl-1H-tetrazole: Tetrazole-based curing accelerator • Perbutyl C: Peroxide-based initiator (manufactured by NOF Corporation) • VR-110: Azo-based initiator (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.)

[0560] <(F) Component: Thermosetting monomer> • DCP: Tricyclodecane dimethanol dimethacrylate (manufactured by Shin-Nakamura Chemical Industry Co., Ltd.) • DAD: Diallyl diphenate (Nisshoku Techno Fine Chemical) ALP-d: Bis[3-allyl-4-(3,4-dihydro-2H-1,3-benzoxazine-3-yl)phenyl]methane, manufactured by Shikoku Chemicals Co., Ltd. • L-DAIC: Manufactured by Shikoku Chemicals Co., Ltd. DVB: Divinylbenzene

[0561] <(G) Component: Organic filler> • EXL-2655: Core shell rubber (manufactured by Dow Chemical)

[0562] <(H) component: thermoplastic resin> • "Synthesis Example 11": A solution of polyimide resin H obtained in Synthesis Example 11 and 20% by mass of non-volatile components. • YX7891T30: Phenoxy resin (manufactured by Mitsubishi Chemical Corporation, toluene solution with 30% by mass of non-volatile content)

[0563] The results obtained from test examples 1 to 6 are shown in Tables 1, 2, and 3.

[0564] [Table 1]

[0565] [Table 2]

[0566] [Table 3]

Claims

1. (A) Compounds containing one or more 2,2,6,6-tetramethylpiperidine-1-oxyl structures in the molecule (B) inorganic filler, (C) Maleimide resin, and (D) Contains vinyl resin having a specific structure, (D) Component is (D-1) A vinyl resin containing a structural unit represented by the following formula (D1-1) and an end group represented by the following formula (y), (D-2) A vinyl resin containing a structural unit represented by the following formula (D2-1) and an end group represented by the following formula (y), And, (D-3) A resin composition comprising a resin selected from the group consisting of vinyl resins containing a radical polymerizable group having a vinyl structure and an active ester moiety. 【Chemistry 1】 (In formula (D1-1), R １ Each of these independently represents a divalent nitrogen-containing heteroaromatic group which may have substituents, R ２ Each of these independently represents a divalent organic group. X １ These are independently -O-, -S-, or -N(R) ３ ) represents, R ３ (This represents a hydrogen atom, a monovalent hydrocarbon group having 1 to 20 carbon atoms, a monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms, or a group in which the hydrocarbon group or a part of the halogenated hydrocarbon group is substituted with at least one atom selected from oxygen and sulfur atoms.) 【Chemistry 2】 (In formula (y), Y represents a monovalent organic group with 3 to 50 carbon atoms containing a vinyl structure, other than a maleimide group, and the wavy line indicates a bonding site. 【Transformation 3】 (In formula (D2-1), R ２１ Each of these independently represents a divalent nitrogen-containing heteroaromatic group which may have substituents, R ２２ Each of these independently represents a divalent aromatic hydrocarbon group which may have substituents, R ２３ This represents a hydrocarbon group having 1 to 20 carbon atoms, to which one or more groups represented by the following formula (d1) are bonded. X ２ each independently represents -O-, -S-, or -N(R ２４ )-, R ２４ (This represents a hydrogen atom, a monovalent hydrocarbon group having 1 to 20 carbon atoms, a monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms, or a group in which the hydrocarbon group or a part of the halogenated hydrocarbon group is substituted with at least one atom selected from oxygen and sulfur atoms.) 【Chemistry 4】 (In formula (d1), * indicates a bonding site with a hydrocarbon group having 1 to 20 carbon atoms. ** indicates the bonding site with other structural units contained in component (D), R ２２ and X ２ These are, respectively, R in the above formula (D2-1). ２２ and X ２ (It is similar to this.)

2. In equation (D1-1), R ２ The resin composition according to claim 1, wherein the group represented by contains a group represented by the following formula (D1-2). 【Transformation 5】 (In formula (D1-2), Ar １ and Ar ２ Each of these independently represents a divalent aromatic group which may have substituents, Each L independently represents a single bond or a divalent linking group. R ４ and R ５ Each of these independently represents a single bond or an alkylene group with 1 to 4 carbon atoms. m1 represents an integer from 0 to 5. The wavy line indicates a connection point.

3. The resin composition according to claim 2, wherein in formula (D1-2), the group represented by L is any of the divalent groups represented by the following formulas (D1-4-1) to (D1-4-3). 【Transformation 6】 (In formulas (D1-4-1) to (D1-4-3), R Ｄ２１ Each of these independently represents a monovalent group selected from a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 14 carbon atoms. R Ｄ２２ Each of these independently represents a monovalent group selected from alkyl groups having 1 to 4 carbon atoms and aryl groups having 6 to 14 carbon atoms. m6 and m7 each independently represent integers from 0 to 4. The wavy line indicates a connection point.

4. The resin composition according to claim 1, wherein the weight-average molecular weight (Mw) of component (D-1) is 2,000 or more and 6,000 or less.

5. In equations (D2-1) and (d1), R ２２ The resin composition according to claim 1, wherein each of the groups represented by the following formula (D2-2) independently has a structure represented by the following formula. 【Transformation 7】 (In formula (D2-2), * is R in the above formula (D2-1) ２３ This represents the bonding site with a hydrocarbon group having 1 to 20 carbon atoms, *** is X in formula (D2-1) or formula (d1) ２ This represents the connection site, R ２５ This represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or a cycloalkyl group having 3 to 10 carbon atoms. n Ｄ１ This represents an integer between 0 and 2, n Ｄ２ (This represents an integer between 0 and 4.)

6. The resin composition according to claim 5, wherein the structure represented by formula (D2-2) is the following formula (D2-3-1) or the following formula (D2-3-2). 【Transformation 8】 (In formulas (D2-3-1) and (D2-3-2), R ２６ Each of these independently represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or a cycloalkyl group having 3 to 10 carbon atoms. n Ｄ３ This represents an integer from 0 to 3, n Ｄ４ This represents an integer between 0 and 2, *, ***, R ２５ , and n Ｄ１ These are *, ***, and R in the above formula (D2-2), respectively. ２５ and n Ｄ１ It is synonymous with, The wavy line indicates a connection point.

7. The resin composition according to claim 1, wherein component (D-2) further contains a structural unit represented by formula (D1-1).

8. The resin composition according to claim 1, wherein the weight-average molecular weight (Mw) of component (D-2) is 3,000 or more and 30,000 or less.

9. The resin composition according to claim 1, wherein the content of component (D) is 5% by mass or more and 25% by mass or less, when the nonvolatile components in the resin composition are taken as 100% by mass.

10. The resin composition according to claim 1, wherein in formula (y), the group represented by Y contains a monovalent aromatic group containing a radical polymerizable group.

11. The resin composition according to claim 1, wherein in formula (y), the group represented by Y is a vinylbenzyl group.

12. The resin composition according to claim 1, wherein the content of component (B) is 60% by mass or more relative to 100% by mass of the nonvolatile components in the resin composition.

13. The resin composition according to claim 1, further comprising (E) a curing accelerator.

14. The resin composition according to claim 13, wherein component (E) is a curing accelerator selected from the group consisting of imidazole-based curing accelerators, benzotriazole-based curing accelerators, tetrazole-based curing accelerators, peroxide-based radical polymerization initiators, and azo-based radical polymerization initiators.

15. The resin composition according to claim 13, wherein component (E) is an imidazole-based curing accelerator.

16. The resin composition according to claim 1, further comprising (F) a thermosetting monomer.

17. The resin composition according to claim 16, wherein component (F) contains a cyclic structure.

18. The resin composition according to claim 16, wherein component (F) contains one or more functional groups selected from the group consisting of vinyl groups, allyl groups, (meth)acryloyl groups, and amino groups.

19. The resin composition according to claim 16, wherein component (F) comprises a benzoxazine resin.

20. The resin composition according to claim 1, further comprising (G) an organic filler.

21. The resin composition according to claim 1, further comprising (H) a thermoplastic resin.

22. A resin sheet comprising a support and a resin composition layer formed on the support, wherein the resin composition layer contains the resin composition according to any one of claims 1 to 21.

23. A circuit board comprising a cured product of the resin composition according to any one of claims 1 to 21.

24. A semiconductor device comprising the circuit board described in claim 23.

25. A method for manufacturing a circuit board, comprising the following steps (I) to (V). (I) A step of laminating the resin sheet described in claim 22 onto an inner layer substrate such that the resin composition layer of the resin sheet and the inner layer substrate are bonded together. (II) A step of curing the resin composition layer to form an insulating layer, (III) A step of forming holes in the insulating layer, (IV) Process of applying desmear treatment to the insulating layer, (V) Step of forming a conductive layer on the surface of the insulating layer after desmear treatment.

26. (I) A step of laminating a resin sheet onto an inner layer substrate such that the resin composition layer of the resin sheet and the inner layer substrate are bonded together. (II) A step of curing the resin composition layer to form an insulating layer, (III) A step of forming holes in the insulating layer, (IV) Process of applying desmear treatment to the insulating layer, (V) The resin sheet according to claim 22 for use in a method for manufacturing a circuit board, which includes a step of forming a conductive layer on the surface of an insulating layer after desmearing.

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