Resin composition

Abstract

Provided is a resin composition which is capable of providing a cured product having a low dielectric loss tangent, excellent adhesion strength with a conductor layer, and excellent good mechanical properties. A resin composition containing (A) a compound containing a specific structural unit and a specific terminal group, (B) a maleimide resin, (C) a phosphorus-based flame retardant, and (D) an inorganic filler.

Description

TECHNICAL FIELD

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

[0002] A cured product formed by curing the resin composition can be used as an insulating layer of a circuit board of a semiconductor device. With the recent high speed of communication, in order to reduce transmission loss when working in a high frequency environment, the insulating material of the circuit board needs an insulating material excellent in dielectric properties (low dielectric loss tangent). As the insulating material, resin described in Patent Documents 1 and 2 are known.

[0003] PRIOR ART DOCUMENTS

[0004] PATENT DOCUMENTS

[0005] Patent Document 1: International Publication No. 2022 / 210095

[0006] Patent Document 2: International Publication No. 2024 / 053282. SUMMARY

[0007] PROBLEMS TO BE SOLVED BY THE INVENTION

[0008] From the viewpoint of reducing transmission loss, sometimes a resin composition containing a large amount of a maleimide resin and an inorganic filler material is used. In addition, sometimes a flame retardant is blended in order to improve the flame retardancy of the board. However, a resin composition combining a maleimide resin, an inorganic filler material, and a flame retardant sometimes causes a problem of an increase in dielectric constant or dielectric properties due to the addition of the flame retardant. In addition, it sometimes results in a cured product poor in adhesion strength to a conductor layer or mechanical properties.

[0009] The present application is an application made in view of the problems described above, and provides: a resin composition which can bring a cured product low in dielectric loss tangent, excellent in adhesion strength to a conductor layer, and excellent in good mechanical properties (specifically, puncture strength); a resin sheet using the resin composition; a circuit board including a cured product of the resin composition; and a semiconductor device including the circuit board.

[0010] MEANS FOR SOLVING THE PROBLEMS

[0011] The present inventors made intensive studies in order to solve the problems described above. As a result, the present inventors found that a resin composition combining (A) a compound containing a specific structural unit and a specific terminal group, (B) a maleimide resin, (C) a phosphorus-based flame retardant, and (D) an inorganic filler material can solve the problems described above, and thus completed the present application.

[0012] That is, the present application includes the following.

[0013] [1] A resin composition comprising:

[0014] (A-1) a compound containing a structural unit represented by the following formula (A1-1) and a terminal group represented by the following formula (y),

[0015] (B) a maleimide resin,

[0016] (C) a phosphorus-based flame retardant, and

[0017] (D) an inorganic filler,

[0018] wherein, when a non-volatile component in the resin composition is taken as 100% by mass, the content of the (C) component is 0.1% by mass or more and 1% by mass or less,

[0019] [Chemical Formula 1]

[0020]

[0021] in formula (A1-1),

[0022] R 1 each independently represents a 2-valent nitrogen-containing heteroaromatic group which can have a substituent,

[0023] R 2 each independently represents a 2-valent organic group,

[0024] X 1 each independently represents -O-, -S-, or -N(R 3 )-,

[0025] R 3 represents a hydrogen atom, a 1-valent hydrocarbon group having 1 to 20 carbon atoms, a 1-valent 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,

[0026] [Chemical Formula 2]

[0027]

[0028] in formula (y),

[0029] Y represents a 1-valent organic group having 3 to 50 carbon atoms containing a radically polymerizable group other than a maleimide group,

[0030] the wavy line represents a bonding site.

[0031] [2] The resin composition according to [1], wherein, in formula (A1-1), 2 the group represented by R

[0032] [Chemical Formula 3]

[0033]

[0034] in formula (A1-2),

[0035] Ar 1 and Ar 2 each independently represents a divalent aromatic group which can have a substituent,

[0036] L each independently represents a single bond or a divalent linking group,

[0037] R 4 and R 5 each independently represents a single bond or an alkylene group having 1 to 4 carbon atoms,

[0038] m1 represents an integer of 0 to 5,

[0039] the wavy line represents a bonding site.

[0040] [3] The resin composition described in [2], wherein, in formula (A1-2), the group represented by L is any one of divalent groups represented by the following formulae (A1-4-1) to (A1-4-3),

[0041] [Chemical Formula 4]

[0042]

[0043] in formulae (A1-4-1) to (A1-4-3),

[0044] R A21 each 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,

[0045] R A22 each independently represents a monovalent group selected from an alkyl group having 1 to 4 carbon atoms and an aryl group having 6 to 14 carbon atoms,

[0046] m6 and m7 each independently represent an integer of 0 to 4,

[0047] the wavy line represents a bonding site.

[0048] [4] The resin composition described in any one of [1] to [3], wherein the weight average molecular weight (Mw) of the (A-1) component is 2,000 or more and 6,000 or less.

[0049] [5] The resin composition according to any one of [1] to [4], wherein the content of the (A-1) component is 5 mass% or more and 25 mass% or less, when the non-volatile component in the resin composition is taken as 100 mass%.

[0050] [6] A resin composition comprising:

[0051] (A-2) a compound containing a structural unit represented by the following formula (A2-1) and a terminal group represented by the following formula (y),

[0052] (B) a maleimide resin,

[0053] (C) a phosphorus-based flame retardant, and

[0054] (D) an inorganic filler,

[0055] wherein the content of the (C) component is 0.1 mass% or more and 1 mass% or less, when the non-volatile component in the resin composition is taken as 100 mass%,

[0056] [Chemical Formula 5]

[0057]

[0058] in formula (A2-1),

[0059] R 21 each independently represents a 2-valent nitrogen-containing heteroaromatic group which can have a substituent,

[0060] R 22 each independently represents a 2-valent aromatic hydrocarbon group which can have a substituent,

[0061] R 23 represents a hydrocarbon group having 1 to 20 carbon atoms in which one or more groups represented by the following formula (a1) are bonded,

[0062] X 2 each independently represents -O-, -S-, or -N(R 24 )-,

[0063] R 24 represents a hydrogen atom, a 1-valent hydrocarbon group having 1 to 20 carbon atoms, a 1-valent 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,

[0064] [Chemical Formula 6]

[0065] *-R 22 -X 2 -** (a1)

[0066] in formula (a1),

[0067] * indicates the site where a hydrocarbon group with 1 to 20 carbon atoms is bonded.

[0068] ** indicates the site where it bonds with other structural units contained in component (A-2).

[0069] R 22 and X 2 respectively with R in the above formula (A2-1) 22 and X 2 same,

[0070] [Chemical Formula 7]

[0071]

[0072] In formula (y),

[0073] Y represents a monovalent organic group with 3 to 50 carbon atoms containing free radical polymerizable groups other than maleimide groups.

[0074] The wavy line indicates the bonding area.

[0075] [7][6] The resin composition, wherein, in formula (A2-1) and formula (a1), R 22 The groups represented are each independently represented by the structure shown in the following formula (A2-2).

[0076] [Chemical Formula 8]

[0077]

[0078] In formula (A2-2),

[0079] * indicates that R in the above formula (A2-1) 23 The bonding site, in formula (a1), represents the site where it is bonded to a hydrocarbon group having 1 to 20 carbon atoms.

[0080] *** represents X in equation (A2-1) or equation (a1). 2 The bonding site,

[0081] R 25 This refers to alkyl groups having 1 to 10 carbon atoms, alkoxy groups having 1 to 10 carbon atoms, or cycloalkyl groups having 3 to 10 carbon atoms.

[0082] n A1 Represents integers from 0 to 2.

[0083] n A2 Represents integers from 0 to 4.

[0084] [8][7] The resin composition thereof, wherein the structure represented by formula (A2-2) is either formula (A2-3-1) or formula (A2-3-2) below.

[0085] [Chemical Formula 9]

[0086]

[0087] In equations (A2-3-1) and (A2-3-2),

[0088] R 26 Each of these can be independently represented as 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.

[0089] n A3 Represents integers from 0 to 3.

[0090] n A4 Represents integers from 0 to 2.

[0091] *、***、R 25 and n A1 respectively with *, ***, and R in the above formula (A2-2) 25 and n A1 Synonyms

[0092] The wavy line indicates the bonding area.

[0093] The resin composition described in any one of [9][6] to [8], wherein the (A-2) component further contains a structural unit represented by the following formula (A1-1),

[0094] [Chemical Formula 10]

[0095]

[0096] In formula (A1-1),

[0097] R 1 Each can be represented independently as a divalent nitrogen-containing heteroaromatic group that may have substituents.

[0098] R 2 Each can be used independently to represent a divalent organic group.

[0099] X 1 Each can be independently represented as -O-, -S-, or -N(R) 3 )-,

[0100] R 3 A group that represents a hydrogen atom, a monovalent hydrocarbon group having 1 to 20 carbon atoms, a monovalent halohydrocarbon group having 1 to 20 carbon atoms, or a group in which the hydrocarbon group or a portion thereof is substituted by at least one of oxygen and sulfur atoms.

[0101] The resin composition described in any one of

[10] [6] to [9], wherein the weight-average molecular weight (Mw) of component (A-2) is 3,000 or more and 30,000 or less.

[0102] The resin composition described in any one of

[11] [6] to

[10] , wherein, when the non-volatile component in the resin composition is set to 100% by mass, the content of component (A-2) is 5% by mass or more and 25% by mass or less.

[0103] The resin composition described in any one of

[12] [1] to

[11] , wherein the group represented by Y in formula (y) comprises: a monovalent aromatic group containing a free radical polymerizable group.

[0104] The resin composition described in any one of

[13] [1] to

[12] , wherein, in formula (y), the group represented by Y is vinyl benzyl.

[0105] The resin composition described in any one of

[14] [1] to

[13] , wherein when the non-volatile component in the resin composition is set to 100% by mass, the content of component (B) is 5% by mass or more and 25% by mass or less.

[0106] The resin composition described in any one of

[15] [1] to

[13] , wherein, when the non-volatile component in the resin composition is set to 100% by mass, the content of component (B) is 6.5% by mass or more and 21% by mass or less.

[0107] The resin composition described in any one of

[16] [1] to

[15] , wherein component (C) comprises at least one of a phosphazene compound and a compound having a phosphazene structure.

[0108] The resin composition described in any one of

[17] [1] to

[16] , wherein the content of component (C) is 0.01% by mass or more and 3% by mass or less relative to the non-volatile components of 100% by mass of the resin composition layer.

[0109] The resin composition described in any one of

[18] [1] to

[17] , wherein the content of component (C) is 0.03% by mass or more and 3.5% by mass or less relative to the resin component in 100% by mass of the resin composition.

[0110] The resin composition described in any one of

[19] [1] to

[18] , wherein the content of component (D) is 60% by mass or more relative to the non-volatile components in 100% by mass of the resin composition.

[0111] The resin composition described in any one of

[20] [1] to

[19] , wherein the resin composition further comprises (E) a thermoplastic resin.

[0112]

[21]

[20] The resin composition wherein, component (E) comprises at least one selected from polyimide resin, phenoxy resin and polystyrene resin.

[0113]

[22]

[20] The resin composition wherein the content of component (E) is 0.01% by mass or more and 5% by mass or less relative to the non-volatile components in 100% by mass of the resin composition.

[0114] The resin composition described in any one of

[23] [1] to

[22] further comprises (F) a curing accelerator.

[0115]

[24]

[23] The resin composition wherein component (F) comprises at least one of an imidazole curing accelerator and a phosphorus curing accelerator.

[0116] The resin composition of any one of

[25] [1] to

[24] , wherein the resin composition further comprises: (G) a liquid thermosetting resin, wherein it does not include a resin equivalent to maleimide resin.

[0117]

[26]

[25] The resin composition wherein component (G) contains a cyclic structure.

[0118] The resin composition described in

[27]

[25] or

[26] , wherein the (G) component contains one or more functional groups selected from vinyl, allyl, (meth)acryloyl and amino.

[0119] The resin composition described in any one of

[28]

[25] to

[27] , wherein component (G) comprises benzo[…]. Azine resin.

[0120] The resin composition described in any one of

[29]

[25] to

[28] , wherein the content of component (G) is 5% by mass or less relative to the non-volatile components in 100% by mass of the resin composition.

[0121] The resin composition described in any one of

[30]

[25] to

[29] , wherein the content of component (G) is 3% or more and 15% or less by mass relative to the resin component in 100% by mass of the resin composition.

[0122] The resin composition described in any one of

[31]

[25] to

[30] , wherein the mass ratio of component (G) to component (A-1) (component (G) / component (A-1)) is 0.01 or more and 2 or less.

[0123] The resin composition described in any one of

[32]

[25] to

[31] , wherein the mass ratio of component (G) to component (A-2) (component (G) / component (A-2)) is 0.01 or more and 2 or less.

[0124] The resin composition described in any one of

[33]

[25] to

[32] , wherein the mass ratio of component (G) to component (B) (component (G) / component (B)) is 0.01 or more and 2 or less.

[0125] The resin composition described in any one of

[34]

[25] to

[33] , wherein the mass ratio of component (G) to component (D) (component (G) / component (D)) is 0.001 or more and 0.3 or less.

[0126] The resin composition described in any one of

[35] [1] to [5] and

[12] to

[34] , wherein the mass ratio of component (A-1) to component (B) (component (A-1) / component (B)) is 0.1 or more and 5 or less.

[0127] The resin composition described in any one of

[36] [6] to

[35] , wherein the mass ratio of component (A-2) to component (B) (component (A-2) / component (B)) is 0.1 or more and 5 or less.

[0128] The resin composition described in any one of

[37] [1] to

[36] , wherein the mass ratio of component (B) to component (D) (component (B) / (D)) is 0.05 or more and 1 or less.

[0129] The resin composition described in any one of

[38] [1] to [5] and

[12] to

[37] , wherein the mass ratio of component (C) to component (A-1) (component (C) / component (A-1)) is 0.01 or more and 0.1 or less.

[0130] The resin composition described in any one of

[39] [6] to

[38] , wherein the mass ratio of component (C) to component (A-2) (component (C) / component (A-2)) is 0.01 or more and 0.1 or less.

[0131] The resin composition described in any one of

[40] [1] to

[39] , wherein the mass ratio of component (C) to component (B) (component (C) / component (B)) is 0.01 or more and 0.1 or less.

[0132] The resin composition described in any one of

[41] [1] to

[40] , wherein the mass ratio of component (C) to component (D) (component (C) / component (D)) is 0.001 or more and 0.02 or less.

[0133] The resin composition described in any one of

[42]

[25] to

[41] , wherein the mass ratio of component (C) to component (G) (component (C) / component (G)) is 0.001 or more and 0.02 or less.

[0134] The resin compositions described in

[43] [1] to

[42] are free of fluorinated resins.

[0135]

[44] A resin sheet comprising: a support and a resin composition layer formed on the support.

[0136] The resin composition layer comprises any one of the resin compositions described in [1] to

[43] .

[0137]

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

[43] .

[0138]

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

[45] .

[0139] Invention Effects

[0140] According to the present invention, the following can be provided: a resin composition that produces a cured product with low dielectric loss tangent, excellent adhesion strength to the conductor layer, and good mechanical properties (specifically, puncture strength); a resin sheet using the resin composition; a circuit board comprising the cured product of the resin composition; and a semiconductor device comprising the circuit board. Detailed Implementation

[0141] The present invention will now be described with reference to embodiments and examples. However, the present invention is not limited to the embodiments and examples shown below, and may be implemented with modifications that do not depart from the scope of the claims and their equivalents.

[0142] [Explanation of Terminology]

[0143] The solutions described in this specification can be used in combination with each other, without regard to expressions such as "preferred" or "more preferred". For example, the description of numerical ranges can use a range formed by combining the upper and lower limits of each range and the numerical values ​​of the embodiments.

[0144] In this specification, the term "non-volatile component" in relation to the resin composition refers to the component constituting the resin composition other than (I) the organic solvent described later. Furthermore, the term "resin component" in relation to the resin composition refers to the component constituting the non-volatile component of the resin composition other than (D) the inorganic filler described later.

[0145] In this specification, the term "may have substituents" used with respect to compounds or groups, unless otherwise stated, refers to 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 specifically stated, the number of constituent atoms of substituents is excluded. Similarly, when the number of carbon atoms of a compound or group is stated, unless specifically stated, the number of carbon atoms of substituents is excluded.

[0146] In this specification, "aromatic ring" refers to a ring that follows Hückel's rule and contains 4r+2 electrons (r being an integer greater than or equal to 1) in its π-electron system, including monocyclic aromatic rings and fused aromatic rings composed of two or more monocyclic aromatic rings. Unless otherwise specified, monocyclic aromatic rings are preferred. The aromatic ring can be an aromatic carbon ring having only carbon atoms as ring-forming atoms, or an aromatic heterocycle having heteroatoms such as oxygen, nitrogen, and sulfur atoms as ring-forming atoms in addition to carbon atoms. Unless otherwise specified, the number of carbon atoms in the aromatic ring is preferably 3 or more, more preferably 4 or more or 5 or more, further preferably 6 or more, and preferably 24 or less, more preferably 18 or less or 14 or less, and further preferably 10 or less.

[0147] In this specification, the term "aromatic group" refers to a group formed by removing one or more hydrogen atoms from the aromatic ring of an aromatic compound. Specifically, a monovalent aromatic group is a group formed by removing one hydrogen atom from the aromatic ring of an aromatic compound, and a divalent aromatic group is a group formed by removing two hydrogen atoms from the aromatic ring of an aromatic compound. Examples of monovalent aromatic groups include aryl groups that may have substituents and heteroaryl groups that may have substituents; examples of divalent aromatic groups include arylene groups that may have substituents and heteroarylene groups that may have substituents.

[0148] In this specification, the term "aliphatic group" refers to a group after removing one or more hydrogen atoms bonded to an aliphatic carbon of an aliphatic compound. Specifically, a monovalent aliphatic group is a group after removing one hydrogen atom bonded to an aliphatic carbon of an aliphatic compound, and a divalent aliphatic group is a group after removing two hydrogen atoms bonded to an aliphatic carbon of an aliphatic compound. Examples of monovalent aliphatic groups include: alkyl groups that may have substituents, cycloalkyl groups that may have substituents, alkenyl groups that may have substituents, and cycloalkenyl groups that may have substituents. Examples of divalent aliphatic groups include: alkylene groups that may have substituents, cycloalkylene groups that may have substituents, alkenyl groups that may have substituents, and cycloalkenyl groups that may have substituents. 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.

[0149] In this specification, the term "(meth)acryloyl" includes acryloyl, methacryloyl, and combinations thereof. Additionally, the term "(meth)acrylate compound" refers to a compound having a (meth)acryloyl group, including acrylate compounds, methacrylate compounds, and combinations thereof. However, (meth)acrylate compounds do not contain (meth)acrylic acid. It should be noted that the term "(meth)acrylic acid" includes acrylic acid, methacrylic acid, and combinations thereof.

[0150] In the following description, components (A-1) and (A-2) are sometimes collectively referred to as "component (A)". Additionally, the resin composition according to the first embodiment and the resin composition according to the second embodiment are sometimes collectively referred to as "resin composition".

[0151] [Resin Composition]

[0152] One embodiment of the present invention relates to a resin composition comprising (A) a compound containing a specific structural unit and a specific terminal group, (B) a maleimide resin, (C) a phosphorus-based flame retardant, and (D) an inorganic filler.

[0153] [The resin composition according to the first embodiment]

[0154] The resin composition according to the first embodiment of the present invention comprises: (A-1) a compound containing a first specific structural unit and a specific terminal group, (B) a maleimide resin, (C) a phosphorus-based flame retardant, and (D) an inorganic filler. By incorporating components (A-1), (B), (C), and (D) in combination into the resin composition, a cured product with low dielectric loss tangent, excellent adhesion strength to the conductor layer, and excellent mechanical properties (high puncture strength) can be obtained.

[0155] The resin composition according to the first embodiment may further contain optional components in combination with components (A-1), (B), (C), and (D). Examples of optional components include: (E) thermoplastic resin, (F) curing accelerator, (G) liquid thermosetting resin, (H) other additives, and (I) organic solvent. Hereinafter, each component contained in the resin composition according to the first embodiment will be described in detail.

[0156] <(A-1) Compounds containing a first specific structural unit and a specific terminal group>

[0157] The resin composition according to the first embodiment of the present invention comprises (A-1) a compound containing a structural unit represented by the following formula (A1-1) and a terminal group represented by the following formula (y) (a compound containing a first specific structural unit and a specific terminal group) as component (A-1). Hereinafter, the structural unit represented by formula (A1-1) is sometimes referred to as "first specific structural unit" or "structural unit (1)". Component (A-1) may be used alone or in combination of two or more.

[0158] [Chemical Formula 11]

[0159]

[0160] In formula (A1-1),

[0161] R 1 Each can be represented independently as a divalent nitrogen-containing heteroaromatic group that may have substituents.

[0162] R 2 Each can be used independently to represent a divalent organic group.

[0163] X 1 Each can be independently represented as -O-, -S-, or -N(R) 3 )-,

[0164] R 3 A group representing a hydrogen atom, a monovalent hydrocarbon group having 1 to 20 carbon atoms, a monovalent halohydrocarbon group having 1 to 20 carbon atoms, or a group in which the hydrocarbon group or part of the halohydrocarbon group is substituted by at least one selected from oxygen and sulfur atoms.

[0165] [Chemical Formula 12]

[0166]

[0167] In formula (y),

[0168] Y represents a monovalent organic group with 3 to 50 carbon atoms containing free radical polymerizable groups other than maleimide groups.

[0169] The wavy line indicates the bonding area.

[0170] In equation (A1-1), R 1 Each of these groups independently represents a divalent nitrogen-containing heteroaromatic group that may have substituents. A divalent nitrogen-containing heteroaromatic group is a group obtained by removing two hydrogens from the nitrogen-containing heteroaromatic ring of a nitrogen-containing heteroaromatic compound. Examples of nitrogen-containing heteroaromatic rings include: pyrrole ring, pyridine ring, pyrimidine ring, pyrazine ring, pyridazine ring, triazine ring, quinoline ring, isoquinoline ring, quinoxaline ring, phthalazine ring, quinazoline ring, naphthidine ring, carbazole ring, acridine ring, and phenazine ring. R 1 The group represented is preferably a divalent group consisting of a pyrimidine ring that may have substituents.

[0171] As R 1 The substituents that the group may have are not particularly limited. Examples include: halogen atoms, monovalent hydrocarbon groups with 1 to 20 carbon atoms, monovalent halohydrocarbon groups with 1 to 20 carbon atoms, groups in which the hydrocarbon group or part of the halohydrocarbon group is substituted by at least one of oxygen and sulfur atoms, nitro, cyano, amino, groups composed of amine salts, etc.

[0172] Halogen atoms that can be used as substituents include, for example, fluorine, chlorine, bromine, and iodine atoms.

[0173] The substituent is a monovalent hydrocarbon group with 1 to 20 carbon atoms, such as a monovalent aliphatic group, a monovalent aromatic group, or a combination thereof. The monovalent aliphatic group can be either a monovalent saturated aliphatic group or a monovalent unsaturated aliphatic group. The monovalent aliphatic group can be a chain hydrocarbon group, a cyclic hydrocarbon group (i.e., an alicyclic hydrocarbon group), or a combination thereof. Furthermore, the chain hydrocarbon group can be either straight-chain or branched.

[0174] Specific examples of monovalent aliphatic groups include alkyl groups. Examples of alkyl groups include: methyl, ethyl, n-propyl, 2-propyl, n-butyl, isobutyl, tert-butyl, n-pentyl, 1-ethylpropyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, pentyl, cyclopentyl, 2,2-dimethylpropyl, 1,1-dimethylpropyl, n-hexyl, cyclohexyl, 1-ethylbutyl, 2-ethylbutyl, 3-ethylbutyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentylene, 4-methylpentylene, 1,1-dimethylbutylene, 2,2-dimethylbutylene, 3,3-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,3-dimethylbutyl, n-heptyl, 1-methylhexyl, 2-methylhexyl, 3-methylhexyl. 4-Methylhexyl, 5-methylhexyl, 1-ethylpentyl, 2-ethylpentyl, 3-ethylpentyl, 1,1-dimethylpentyl, 2,2-dimethylpentyl, 3,3-dimethylpentyl, 4,4-dimethylpentyl, 1,2-dimethylpentyl, 1,3-dimethylpentyl, 1,4-dimethylpentyl, 2,3-dimethylpentyl, 2,4-dimethylpentyl, 3,4-dimethylpentyl, 2-methyl-3,3-dimethylbutyl, 1-methyl-3,3-dimethylbutyl, 1,2,3-trimethylbutyl, 1,3-dimethyl-2-pentyl, 2-isopropylbutyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 1-cyclohexylmethyl, 2-ethylcyclopentyl, 3-ethylcyclopentyl 2,3-Dimethylcyclopentyl, 2,4-Dimethylcyclopentyl, 2-Methylcyclopentylmethyl, 2-Cyclopentylethyl, 1-Cyclopentylethyl, n-Octyl, 2-Octyl, 3-Octyl, 4-Octyl, 2-Methylheptyl, 3-Methylheptyl, 4-Methylheptyl, 5-Methylheptyl, 6-Methylheptyl, 2-Ethylhexyl, 3-Ethylhexyl, 4-Ethylhexyl, 5-Ethylhexyl, 1,1-Dimethylhexyl, 2,2-Dimethylhexyl, 3,3-Dimethylhexyl, 4,4-Dimethylhexyl, 5,5-Dimethylhexyl, 1,2-Dimethylhexyl, 1,3-Dimethylhexyl, 1,4-Dimethylhexyl, 1,5-Dimethylhexyl, 2,3-Dimethylhexyl, 2,4-Dimethylhexyl, 2, 5-Dimethylhexyl, 1,1-Ethylmethylpentyl, 2,2-Ethylmethylpentyl, 3,3-Ethylmethylpentyl, 4,4-Ethylmethylpentyl, 1-Ethyl-2-methylpentyl, 1-Ethyl-3-methylpentyl, 1-Ethyl-4-methylpentyl, 2-Ethyl-1-methylpentyl, 3-Ethyl-1-methylpentyl, 4-Ethyl-1-methylpentyl, 2-Ethyl-3-methylpentyl, 2-Ethyl-4-methylpentyl, 3-Ethyl-2-methylpentyl, 4-Ethyl-3-methylpentyl, 3-Ethyl-4-methylpentyl, 4-Ethyl-3-methylpentyl, 1-(2-methylpropyl)butyl, 1-(2-methylpropyl)-2-methylbutyl, 1,1-(2-methylpropyl)ethyl, 1,1-(2-Methylpropyl)ethylpropyl, 1,1-diethylpropyl, 2,2-diethylpropyl, 1,1-ethylmethyl-2,2-dimethylpropyl, 2,2-ethylmethyl-1,1-dimethylpropyl, 2-ethyl-1,1-dimethylbutyl, 2,3-dimethylcyclohexyl, 2,3-dimethylcyclohexyl, 2,5-dimethylcyclohexyl, 2,6-dimethylcyclohexyl, 3,5-dimethylcyclohexyl, 2-methylcyclohexylmethyl, 3-methylcyclohexylmethyl, 4-methylcyclohexylmethyl, 2-ethylcyclohexyl, 3-ethylcyclohexyl, 4-ethylcyclohexylmethyl, 2-ethylcyclohexyl, 1-cyclohexylethyl, 1-cyclohexyl-2-ethylidene, nonyl, isononyl, decyl, isodecyl, undecyl, dodecyl, propargyl, etc.

[0175] Specific examples of monovalent aromatic groups include aryl groups. Examples of aryl groups include phenyl, naphthyl, anthracene, and biphenyl (-C6H4-C6H5).

[0176] Examples of "monovalent groups composed of combinations of monovalent hydrocarbon groups with 1 to 20 carbon atoms" include benzyl, 2-phenylethyl, etc.

[0177] Examples of monovalent haloalkyl groups with 1 to 20 carbon atoms that serve as substituents include groups in which some or all of the hydrogen atoms of the monovalent haloalkyl group with 1 to 20 carbon atoms are replaced by halogen atoms. The halogen atom constituting the haloalkyl group is the same as the halogen atom that serves as a substituent as described above.

[0178] The substituent is "a group in which at least one of the oxygen atom and sulfur atom is substituted, either a hydrocarbon group or a portion thereof." Examples of substituents include: a group in which a monovalent hydrocarbon group having 1 to 20 carbon atoms or a portion thereof has been substituted by a group such as -O-, -S-, -C(=O)-, -C(=O)-O-, -S(=O)-, or -S(O)2-.

[0179] The amino group that serves as a substituent can be any of the primary, secondary, and tertiary amino groups. Examples of substituents for secondary and tertiary amino groups include monovalent hydrocarbon groups having 1 to 20 carbon atoms. The situation regarding monovalent hydrocarbon groups having 1 to 20 carbon atoms is as described above.

[0180] Among the substituents formed by amine salts, examples of anions constituting the anionic sites include: Cl... - Known anions, etc.

[0181] From the perspective of the excellent polymerization reactivity in the synthesis of component (A-1), R 1The substituents that the indicated group may have are preferably halogen atoms, hydrocarbon groups with 1 to 6 carbon atoms, halogenated hydrocarbon groups with 1 to 6 carbon atoms, nitro, cyano, amino, or groups composed of amine salts, more preferably fluorine atoms, chlorine atoms, methyl, tert-butyl, phenyl, nitro, cyano, or primary amino, and even more preferably phenyl.

[0182] From the viewpoint of achieving the desired effect of the present invention, R 1 The indicated group preferably has no substituents or has phenyl groups as substituents.

[0183] For R 1 The two bonding sites in the represented group (with X) 1 The location of the bonding sites (equally bonded) is not particularly limited, but from the viewpoint of excellent polymerization reactivity in the synthesis of the (A-1) component, the meta position is preferred. In R 1 In the case where the divalent group is composed of a pyrimidine ring that may have substituents, for example, it is preferable to have a bonding site at the 4,6 carbon position of the pyrimidine ring. Furthermore, in this case, as R... 1 The bonding site of the substituent in the indicated group is preferably on the carbon at the 2-position of the pyrimidine ring.

[0184] In equation (A1-1), R 2 Each of these independently represents a divalent organic group. R 2 The represented group may contain heteroatoms such as oxygen, nitrogen, and sulfur atoms. Among them, R... 2 The represented group preferably contains the group represented by the following formula (A1-2).

[0185] [Chemical Formula 13]

[0186]

[0187] In formula (A1-2),

[0188] Ar 1 and Ar 2 Each can be represented independently as a divalent aromatic group that may have substituents.

[0189] L can independently represent a single bond or a divalent linker.

[0190] R 4 and R 5 Each can be independently represented as a single bond or an alkylene group having 1 to 4 carbon atoms.

[0191] m1 represents an integer from 0 to 5.

[0192] The wavy line indicates the bonding area.

[0193] In equation (A1-2), Ar1 and Ar 2 Each of these represents a divalent aromatic group that can have substituents. Among them, Ar... 1 and Ar 2 Preferably, it is a divalent aromatic group with 6 to 30 carbon atoms, more preferably phenylene, naphthylene, anthraceneylene or biphenylene (-C6H4-C6H4-), and even more preferably phenylene or naphthylene.

[0194] As Ar 1 and Ar 2 Possible substituents include, for example, halogen atoms, monovalent hydrocarbon groups with 1 to 20 carbon atoms, haloalkyl groups with 1 to 20 carbon atoms, alkoxy groups with 1 to 20 carbon atoms, alkylthio groups with 1 to 20 carbon atoms, nitro groups, cyano groups, carboxyl groups, sulfonyl groups, phosphonyl groups, phosphate groups, hydroxyl groups, or primary to tertiary amino groups. Regarding the halogen atom as a substituent, as described above. Preferably, a monovalent hydrocarbon group with 1 to 20 carbon atoms is preferred, and more preferably one or more substituents selected from methyl, vinyl, and allyl groups.

[0195] Ar 1 and Ar 2 The number of substituents is preferably 0 or 1 to 8, more preferably 0 or 1 to 4, and even more preferably 0, 1 or 2.

[0196] In formula (A1-2), L independently represents either a single bond or a divalent linking group. Examples of divalent linking groups represented by L include: divalent groups composed of one or more (e.g., 1 to 3000, 1 to 1000, 1 to 100, or 1 to 50) skeletal atoms selected from carbon, oxygen, nitrogen, and sulfur atoms. Examples of divalent linking groups include: alkylene, alkenylene, arylene, heteroarylene, -O-, -C(=O)-, -C(=O)-O-, -N(R 6 )-(where R 6 The group can represent hydrogen atoms, monovalent hydrocarbon groups with 1 to 20 carbon atoms or monovalent halohydrocarbon groups with 1 to 20 carbon atoms, -C(=O)-NH-, -NC(=O)N-, -S-, -S(=O)-, -S(O)2-, etc., and can be a group composed of multiple of these. Among them, L is preferably any one of single bonds, -O-, -C(=O)-, -C(=O)-O-, -S-, -S(O)2-, and divalent groups represented by the following formulas (A1-3-1) to (A1-3-4), and more preferably any one of the divalent groups represented by the following formulas (A1-4-1) to (A1-4-3).

[0197] [Chemical Formula 14]

[0198]

[0199] In equations (A1-3-1) to (A1-3-4),

[0200] R A11 Each of these groups independently represents a monovalent group selected from hydrogen atoms, alkyl groups having 1 to 12 carbon atoms, aryl groups having 6 to 14 carbon atoms, and aralkyl groups having 7 to 15 carbon atoms.

[0201] R A12 Each of these groups independently represents a monovalent group selected from halogen atoms, alkyl groups with 1 to 12 carbon atoms, alkoxy groups with 1 to 10 carbon atoms, cycloalkyl groups with 3 to 12 carbon atoms, cycloalkoxy groups with 3 to 12 carbon atoms, alkenyl groups with 2 to 10 carbon atoms, aryl groups with 6 to 14 carbon atoms, aryloxy groups with 6 to 14 carbon atoms, aralkyl groups with 7 to 15 carbon atoms, and arylalkoxy groups with 7 to 15 carbon atoms.

[0202] m2 represents an integer from 1 to 10.

[0203] m3 represents an integer from 2 to 7.

[0204] m4 and m5 independently represent integers from 0 to 4.

[0205] The wavy line indicates the bonding area.

[0206] [Chemical Formula 15]

[0207]

[0208] In equations (A1-4-1) to (A1-4-3),

[0209] R A21 Each of these groups independently represents a monovalent group selected from hydrogen atoms, alkyl groups having 1 to 4 carbon atoms, and aryl groups having 6 to 14 carbon atoms.

[0210] R A22 Each of these groups independently represents a monovalent group selected from alkyl groups having 1 to 4 carbon atoms and aryl groups having 6 to 14 carbon atoms.

[0211] m6 and m7 independently represent integers from 0 to 4.

[0212] The wavy line indicates the bonding area.

[0213] In equations (A1-3-1) to (A1-3-3), R A11 Each of these groups independently represents a monovalent group selected from hydrogen atoms, alkyl groups having 1 to 12 carbon atoms, aryl groups having 6 to 14 carbon atoms, and aralkyl groups having 7 to 15 carbon atoms. Furthermore, in formula (A1-3-4), R... A12Each of these groups independently represents a monovalent group selected from halogen atoms, alkyl groups with 1 to 12 carbon atoms, alkoxy groups with 1 to 10 carbon atoms, cycloalkyl groups with 3 to 12 carbon atoms, cycloalkoxy groups with 3 to 12 carbon atoms, alkenyl groups with 2 to 10 carbon atoms, aryl groups with 6 to 14 carbon atoms, aryloxy groups with 6 to 14 carbon atoms, aralkyl groups with 7 to 15 carbon atoms, and arylalkoxy groups with 7 to 15 carbon atoms.

[0214] As R A11 Or R A12 Alkyl groups with 1 to 12 carbon atoms can be exemplified by methyl, ethyl, propyl, butyl, etc.

[0215] As R A11 Or R A12 The aryl groups represented by carbon atoms numbering 6 to 14 include, for example, phenyl, naphthyl, anthracene, biphenyl (-C6H4-C6H5), etc.

[0216] As R A11 Or R A12 Aryl groups representing 7 to 15 carbon atoms include, for example, benzyl and phenylethyl.

[0217] As R A12 The alkoxy groups representing 1 to 10 carbon atoms include, for example: methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, heptoxy, octoxy, etc.

[0218] As R A12 Examples of cycloalkyl groups with 3 to 12 carbon atoms include cyclopropyl, cyclobutyl, cyclobutyl, cyclopentyl, and cyclohexyl.

[0219] As R A12 Examples of cycloalkoxy groups representing carbon atoms with 3 to 12 carbon atoms include cyclopropoxy, cyclobutoxy, and cyclobutoxy.

[0220] As R A12 The alkenyl groups represented by carbon atoms numbering 2 to 10 include, for example, vinyl and propenyl groups.

[0221] As R A12 The aryloxy groups that represent 6 to 14 carbon atoms include, for example, phenoxy and naphthoxy.

[0222] As R A12 The arylalkoxy groups representing 7 to 15 carbon atoms include, for example, benzyloxy and phenylethoxy.

[0223] In formula (A1-3-1), m2 represents an integer from 1 to 10, preferably an integer from 1 to 6.

[0224] In formula (A1-3-3), m3 represents an integer from 2 to 7, preferably 4 or 5.

[0225] In formula (A1-3-4), m4 and m5 independently represent integers from 0 to 4, preferably 0 or 1, and more preferably 0.

[0226] In equations (A1-4-1) to (A1-4-3), R A21 Each of these groups independently represents a monovalent group selected from hydrogen atoms, alkyl groups having 1 to 4 carbon atoms, and aryl groups having 6 to 14 carbon atoms. Additionally, R... A22 Each of the following groups independently represents a monovalent group selected from alkyl groups having 1 to 4 carbon atoms and aryl groups having 6 to 14 carbon atoms.

[0227] As R A21 Or R A22 Alkyl groups representing 1 to 4 carbon atoms include, for example, methyl, ethyl, propyl, butyl, etc.

[0228] As R A21 Or R A22 Aryl groups representing 6 to 14 carbon atoms include, for example, phenyl and naphthyl.

[0229] In formula (A1-4-3), m6 and m7 independently represent integers from 0 to 4, preferably 0 or 1, and more preferably 0.

[0230] In formula (A1-2), the divalent linker represented by L can have R 6 It represents a monovalent hydrocarbon group with 1 to 20 carbon atoms or a monovalent halohydrocarbon group with 1 to 20 carbon atoms.

[0231] As R 6 The monovalent hydrocarbon group representing 1 to 20 carbon atoms, and as R 1 The group represented may have substituents of "monovalent hydrocarbon groups with 1 to 20 carbon atoms".

[0232] As R 6 The monovalent haloalkyl group representing 1 to 20 carbon atoms, and as R 1 The group represented may have substituents of "monovalent haloalkyl groups with 1 to 20 carbon atoms".

[0233] In equation (A1-2), R 4 and R 5 Each can be independently represented by a single bond or an alkylene group having 1 to 4 carbon atoms. Examples of alkylene groups having 1 to 4 carbon atoms include: methylene, ethylene, n-propylene, isopropylene, n-butylene, and secondary butylene. Among them, R... 4 and R 5The indicated group is preferably a single bond, methylene, or ethylene.

[0234] In formula (A1-2), m1 represents an integer from 0 to 5, preferably an integer from 0 to 4, and more preferably an integer from 0 to 3.

[0235] In formula (A1-1), X 1 Each can be independently represented as -O-, -S-, or -N(R) 3 )-. Additionally, X 1 The represented group may have R 3 This refers to a group that represents a hydrogen atom, a monovalent hydrocarbon group having 1 to 20 carbon atoms, a monovalent halohydrocarbon group having 1 to 20 carbon atoms, or a group in which the hydrocarbon group or a portion thereof is substituted by at least one atom selected from oxygen and sulfur atoms. It should be noted that when there are two or more X atoms... 1 They are -N(R) 3 In the case of )-, X 1 The R represented by the group 3 They can be the same or different.

[0236] As R 3 The monovalent hydrocarbon groups representing 1 to 20 carbon atoms, and R as in formula (A1-1) 1 The group represented may have substituents of "monovalent hydrocarbon groups with 1 to 20 carbon atoms".

[0237] As R 3 The monovalent haloalkyl group representing 1 to 20 carbon atoms, and R as in formula (A1-1) 1 The group represented may have substituents of "monovalent haloalkyl groups with 1 to 20 carbon atoms".

[0238] As R 3 The phrase "the hydrocarbon group or part of the halohydrocarbon group is substituted by at least one group selected from oxygen and sulfur atoms" is related to R in formula (A1-1). 1 The group represented may have substituents, meaning that "the hydrocarbon group or part of the halohydrocarbon group is selected from at least one substituent of oxygen and sulfur atoms".

[0239] In formula (y), Y represents a monovalent organic group with 3 to 50 carbon atoms containing free radical polymerizable groups other than maleimide groups.

[0240] Examples of free radical polymerizable groups that can be represented by Y include: vinyl, 1-propenyl, allyl (2-propenyl), isopropenyl, vinylphenyl, styryl, (meth)acryloyl, fumaroyl, etc.

[0241] The group represented by Y may contain only a free radical polymerizable group, or it may contain a free radical polymerizable group separated by a divalent linker. Examples of divalent linkers include: alkylene, alkenylene, arylene, heteroarylene, -O-, -C(=O)-, -C(=O)-O-, -NH-, -C(=O)-NH-, -NC(=O)N-, -S-, -S(=O)-, -S(O)2-, etc., and can be a group composed of multiple of these. Preferably, the divalent linker is alkylene, and more preferably methylene.

[0242] In a suitable embodiment, the group represented by Y comprises a monovalent aromatic group containing a free radical polymerizable group. More preferably, the group represented by Y is a monovalent group selected from vinylphenyl, allylphenyl, isopropenylphenyl, and vinylbenzyl, and more preferably vinylbenzyl.

[0243] In a suitable embodiment, (A-1) is separated by a divalent linker and contains a group represented by Y. Preferably, the (A-1) component contains at least one of the terminal groups represented by the following formulas (A1-5-1) and (A1-5-2).

[0244] [Chemical Formula 16]

[0245]

[0246] In equations (A1-5-1) and (A1-5-2),

[0247] X A1 Indicates a single bond, -O-, -S-, or -N(R) 3 )-;

[0248] Regarding the other symbols, see above.

[0249] In equations (A1-5-1) and (A1-5-2), X A1 Indicates a single bond, -O-, -S-, or -N(R) 3 )-. About X A1 The represented group may have R 3 As mentioned above.

[0250] (A-1) Components can be synthesized using substances synthesized by known methods. (A-1) Components can be synthesized, for example, as follows: [The following text appears to be a separate, unrelated sentence: "Containing R..."] 1 The structure of the represented group is a raw material compound containing R. 2The starting material compound containing the group represented by Y, the starting material compound containing the group represented by Y, and the compound containing other structural units as needed are heated together in an organic solvent with an alkali metal or alkali metal compound (and a polymerization inhibitor as needed). Regarding the starting material compound containing the group represented by Y and the compound containing other structural units (structural units other than structural unit (1)), it is possible to heat the compound containing R... 1 The structure of the represented group in the raw material compound and the compound containing R 2 After the raw material compound representing the structure of the group is reacted, it is heated and mixed to allow it to react.

[0251] In the synthesis of component (A-1), as a component containing R 1 Examples of starting material compounds with the represented group structure 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, 2-chloro-5-iodopyrimidine, 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 Pyrimidine compounds such as 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, and 5-bromo-4-chloro-2-methylthiopyrimidine; 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 can be used alone or in combination of two or more.

[0252] In the synthesis of component (A-1), as a component containing R 2Examples of raw material compounds with the indicated group structure include: 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-dimethylbutylene)bisphenol, and 1,1-bis(4-hydroxyphenyl)propane. Nonane, bis(4-hydroxyphenyl) sulfone, 1,1-bis(4-hydroxyphenyl)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-propyl]benzene, 4,4'-cyclododecyl bisphenol, 4,4'-decyl bisphenol, 4,4'-dihydroxy-2,2',3,3',5,5'-hexamethylbiphenyl and other bisphenol compounds; "Priplast" manufactured by Croda Japan. Diol compounds such as “Priplast 1901”, “Priplast 1838”, “Priplast 3186”, “Priplast 3192”, “Priplast 3197”, and “Priplast 3199”. These compounds can be used alone or in combination of two or more.

[0253] In the synthesis of component (A-1), the starting material compounds containing the group represented by Y can be, for example, monovalent phenolic compounds such as 4-isopropenylphenol, 4-vinylphenol, 2-allylphenol, isoeugenol, and tocotrienol; monovalent amine compounds such as diallylamine; monovalent thiols such as 2-propen-1-thiol; monovalent aliphatic halides such as allyl chloride, 4-(chloromethyl)styrene, and 3-(chloromethyl)styrene; monovalent acyl halides such as acryloyl chloride, methacryloyl chloride, crotonyl chloride, and cinnamoyl chloride; and monovalent acid anhydrides such as acrylic anhydride, crotonic anhydride, and methacrylic anhydride. These compounds can be used individually or in combination of two or more.

[0254] When component (A-1) contains other structural units (structural units other than structural unit (1)), compounds derived from these other structural units may include, for example: diphenyl carbonate, thiodiphenyl carbonate, selenodiphenyl carbonate, phosgene, sulfophosgene, selenophosgene, and other compounds that derive structural units containing carbonate bonds, thiocarbonate bonds, or selenocarbonate bonds; dihydroxy compounds such as benzyl glycol and cyclohexanediethanol; phosphine oxide compounds such as bis(fluorophenyl)phenylphosphine oxide, bis(fluorophenyl)naphthylphosphine oxide, and bis(fluorophenyl)anthraylphosphine oxide; and dihalides of dicarboxylic acids such as phthaloyl dichloro, isophthaloyl dichloro, and terephthaloyl dichloro. These compounds may be used individually or in combination of two or more.

[0255] In the synthesis of component (A-1), when using compounds with hydroxyl groups, such as phenolic compounds, as raw materials, alkali metals and alkali metal compounds react with these hydroxyl-containing compounds to form alkali metal salts. 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. Alkali metal carbonates are preferred, and potassium carbonate is more preferred.

[0256] In the synthesis of component (A-1), examples of organic solvents include: tetrahydrofuran (THF), dihydrofuran (THF), and dihydrofuran (THF). Ether solvents such as alkanes, cyclopentylmethyl ethers, anisoles, phenethyl ethers, diphenyl ethers, dialkoxybenzenes, and trimekoxybenzenes; nitrogen-containing solvents such as N,N-dimethylacetamide (DMAc), N,N-dimethylformamide, N-methyl-2-pyrrolidone, and 1,3-dimethyl-2-imidazolinone; ester 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 solvents such as benzophenone, 2-heptanone, cyclohexanone, and methyl ethyl ketone; halogen solvents such as dichloromethane, 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.

[0257] In the synthesis of component (A-1), from the viewpoint of controlling the polymerization reaction and obtaining component (A-1) with the desired molecular weight, polymerization inhibitors can be used. Examples of polymerization inhibitors include quinones, hindered phenolic compounds, hindered amine compounds, and amine compounds.

[0258] Quinones that can be used as polymerization inhibitors include, for example, 2-tert-butyl-p-benzoquinone, 2,5-diphenyl-p-benzoquinone, chloroquinone, and trimethylquinone.

[0259] Hindered phenolic compounds that act as polymerization inhibitors include, for example, 1,6-hexanediol-bis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], 2,4-bis-(n-octylthio)-6-(4-hydroxy-3,5-di-tert-butylaniline)-3,5-triazine, pentaerythritol tetra[3-(3,5-tert-butyl-4-hydroxyphenyl)propionate], 2,2-thiodiethylidene bis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], and deca[[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate]. Octadecyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate, tris-(3,5-di-tert-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, 1,3,5-tris(3,5-di-tert-butyl-4-hydroxyphenylmethyl)-2,4,6-trimethylbenzene, etc. Hindered phenolic compounds used as polymerization inhibitors can be commercially available products, such as "AO-020" and "A-330" manufactured by ADEKA.

[0260] Hindered amine compounds used as polymerization inhibitors include, for example, 4-cyclohexylcarbonyloxy-2,2,6,6-tetramethylpiperidinoxy, 4-benzoyloxy-2,2,6,6-tetramethylpiperidinoxy, 2,2,6,6-tetramethyl-4-hydroxypiperidin-1-oxy, and 4,4'-[1,10-dioxo-1,10-decadiyl)bis(oxy)]bis[2,2,6,6-tetramethyl]-1-piperidinoxy. Commercially available products can be used as polymerization inhibitors, such as "ADKSTAB LA-7RD" manufactured by ADEKA and "IRGASTAB UV 10" manufactured by BASF.

[0261] Examples of amine compounds that can be used as polymerization inhibitors include phenothiazine, 3,7-diisopropylphenylphenothiazine, N,N'-diphenyl-1,4-phenylenediamine, and N,N'-di-2-naphthyl-1,4-phenylenediamine.

[0262] In the synthesis of component (A-1), R is included. 1 The structure of the represented group in the raw material compound and the compound containing R 2The reaction temperature for reacting the reactant compound with the indicated group structure is preferably 50°C or higher, more preferably 80°C or higher, preferably 300°C or lower, and even more preferably 200°C or lower. Furthermore, the reaction time is preferably 1 hour or higher, more preferably 2 hours or higher, even more preferably 3 hours or higher, preferably 100 hours or lower, even more preferably 50 hours or lower, and even more preferably 25 hours or lower.

[0263] In the synthesis of component (A-1), when R is included... 1 The structure of the represented group in the raw material compound and the compound containing R 2 When a starting compound containing the group represented by Y is reacted, and then a starting compound containing the group represented by Y (and, if necessary, compounds from which other structural units are derived) 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. Furthermore, the reaction time is preferably 1 hour or higher, more preferably 2 hours or higher, even more preferably 3 hours or higher, preferably 50 hours or lower, more preferably 25 hours or lower, and even more preferably 15 hours or lower.

[0264] The weight-average molecular weight (Mw) of component (A-1) is, for example, 100 or more, preferably 1,000 or more, more preferably 1,500 or more, and 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 (A-1) is, for example, 500,000 or less, preferably 100,000 or less, more preferably 10,000 or less, and even more preferably 6,000 or less, 5,000 or less, or 4,500 or less. The weight-average molecular weight (Mw) of component (A-1) can be determined using gel permeation chromatography (GPC) as a polystyrene conversion value.

[0265] When all structural units contained in component (A-1) are set to 100 mol%, the content of structural unit (1) in component (A-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.

[0266] In the resin composition according to the first embodiment, from the viewpoint of better exerting the desired effect of the present invention, the content of component (A-1) in the resin composition is preferably 1% by mass or more, more preferably 3% by mass or more, and even more preferably 5% by mass or more, 6% by mass or more, 7% by mass or more, 8% by mass or more, 10% by mass or more, 11% by mass or more, 12% by mass or more, or 13% by mass or more, relative to the non-volatile components in 100% by mass of the resin composition. In one embodiment, the lower limit of the content of component (A-1) in the resin composition relative to the non-volatile components in 100% by mass of the resin composition may be 14% by mass or more, 15% by mass or more, 16% by mass or more, 18% by mass or more, 20% by mass or more, or 21% by mass or more.

[0267] From the viewpoint of maximizing the desired effects of the present invention, the upper limit of the content of component (A-1) in the resin composition relative to the non-volatile components in 100% by mass of the resin composition is preferably 35% by mass or less, more preferably 30% by mass or less, and even more preferably 25% by mass or less, 23% by mass or less, 21% by mass or less, 20% by mass or less, or 18% by mass or less. In one embodiment, the upper limit of the content of component (A-1) in the resin composition relative to the non-volatile components in 100% by mass of the resin composition may be 16% by mass or less, 15% by mass or less, 14% by mass or less, 13% by mass or less, 12% by mass or less, 11% by mass or less, 10% by mass or less, 8% by mass or less, 7% by mass or less, or 6% by mass or less.

[0268] In the resin composition according to the first embodiment, from the viewpoint of better exerting the desired effect of the present invention, the content of component (A-1) in the resin composition is preferably 10% by mass or more, more preferably 15% by mass or more, and even more preferably 20% by mass or more, 25% by mass or more, 30% by mass or more, 35% by mass or more, 40% by mass or more, or 42% by mass or more, relative to the resin component in 100% by mass of the resin composition. In one embodiment, the lower limit of the content of component (A-1) in the resin composition relative to the non-volatile components in 100% by mass of the resin composition may be 45% by mass or more, 50% by mass or more, 55% by mass or more, 60% by mass or more, 71% by mass or more, or 73% by mass or more.

[0269] From the viewpoint of maximizing the desired effects of the present invention, the upper limit of the content of component (A-1) in the resin composition relative to the resin component in 100% by mass of the resin composition is preferably 85% by mass or less, more preferably 75% by mass or less, and even more preferably 73% by mass or less, 71% by mass or less, 60% by mass or less, 55% by mass or less, or 50% by mass or less. In one embodiment, the lower limit of the content of component (A-1) in the resin composition relative to the resin component in 100% by mass of the resin composition may be 45% by mass or less, 42% by mass or less, 40% by mass or less, 35% by mass or less, 30% by mass or less, 25% by mass or less, or 20% by mass or less.

[0270] <(B) Maleimide Resin>

[0271] The resin composition according to the first embodiment of the present invention includes (B) maleimide resin as component (B). The (B) maleimide resin does not contain any substance equivalent to component (A-1) described above. The (B) maleimide resin may be used alone or in combination of two or more types.

[0272] (B) The maleimide resin may be an aromatic maleimide resin having maleimide groups directly bonded to the aromatic ring, or an aliphatic maleimide resin not having maleimide groups directly bonded to the aromatic ring. When (B) the maleimide resin comprises an aliphatic maleimide resin, it is preferable that the resin comprises a maleimide resin having a carbon skeleton derived from a dimer acid. When (B) the maleimide resin comprises an aromatic maleimide resin, it is preferable that the resin comprises a maleimide resin having one or more skeletons selected from a biphenyl skeleton, an indane skeleton, and an aralkyl skeleton.

[0273] The carbon skeleton of a dimer acid refers to a carbon skeleton obtained by removing the two terminal carboxyl groups (-COOH) from the dimer acid, or by replacing the two terminal carboxyl groups (-COOH) with methylene groups (-CH2-). Dimer acids are known compounds obtained by dimerizing unsaturated fatty acids (preferably unsaturated fatty acids with 11 to 22 carbon atoms, more preferably unsaturated fatty acids with 14 to 20 carbon atoms, and particularly preferably unsaturated fatty acids with 18 carbon atoms), and their industrial manufacturing processes are basically standardized in the industry. Dimer acids that are particularly easy to obtain include those with 36 carbon atoms obtained by dimerizing inexpensive and readily available 18-carbon unsaturated fatty acids such as oleic acid and linoleic acid as the main component. In addition, depending on the manufacturing method, degree of purification, etc., dimer acids sometimes contain arbitrary amounts of monomeric acids, trimer acids, other polymeric fatty acids, etc. In addition, double bonds remain after the polymerization reaction of unsaturated fatty acids, but in this specification, hydrides that undergo further hydrogenation to reduce the degree of unsaturation are also included in dimer acids.

[0274] Examples of maleimide resins having a carbon skeleton derived from dimer acids include maleimide resins represented by the following formula (B1).

[0275] [Chemical Formula 17]

[0276]

[0277] In formula (B1),

[0278] Each of the q1+1 Ws independently represents a divalent organic group composed of five or more skeletal atoms selected from carbon atoms, nitrogen atoms (nitrogen atoms that do not form imides), oxygen atoms and sulfur atoms, as well as 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.

[0279] Each of the q1 Zs independently represents a tetravalent organic group composed of five or more skeletal atoms selected from carbon, nitrogen (nitrogen atoms that do not form imides), oxygen, and sulfur, as well as non-skeletal atoms selected from hydrogen and halogen atoms.

[0280] q1 represents an integer greater than or equal to 0.

[0281] In formula (B1), each of the q1+1 Ws independently represents a divalent organic group composed of five or more (preferably five to 200, more preferably five to 100, and even more preferably five to 50) skeletal atoms selected from carbon atoms, nitrogen atoms (nitrogen atoms that do not form imides), oxygen atoms, and sulfur atoms, as well as non-skeletal atoms selected from hydrogen atoms and halogen atoms, and at least one of the q1+1 Ws represents a divalent hydrocarbon group derived from a dimer acid.

[0282] The divalent hydrocarbon group derived from dimer acid refers to a divalent hydrocarbon group formed by removing the two terminal carboxyl groups (-COOH) of the dimer acid, or by replacing the two terminal carboxyl groups (-COOH) with methylene groups (-CH2-).

[0283] The q1+1 W may have divalent organic groups other than divalent hydrocarbon groups from dimer acids. When the q1+1 X is set to 100 mol%, it is preferable that 30 mol% or more of them are divalent hydrocarbon groups from dimer acids, more preferably 60 mol% or more are divalent hydrocarbon groups from dimer acids, even more preferably 90 mol% or more are divalent hydrocarbon groups from dimer acids, and even more preferably all of the q1+1 W are divalent hydrocarbon groups from dimer acids.

[0284] The divalent organic groups in q1+1 W, excluding the divalent hydrocarbon groups from dimer acids, can be divalent organic groups without aromatic rings or divalent organic groups with aromatic rings.

[0285] In formula (B1), each of the q1 Zs independently represents a tetravalent organic group composed 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 (nitrogen atoms that do not form imides), oxygen atoms, and sulfur atoms, as well as non-skeletal atoms selected from hydrogen atoms and halogen atoms. The tetravalent organic group represented by Z can be a tetravalent organic group without an aromatic ring or a tetravalent organic group with an aromatic ring.

[0286] In one embodiment, the tetravalent organic group represented by Z is preferably a tetravalent group selected from the following formulas (Z1) to (Z5).

[0287] [Chemical Formula 18]

[0288]

[0289] In equations (Z1) to (Z5),

[0290] 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 55Each can be used to independently represent an aromatic ring that may have substituents or a non-aromatic ring that may have substituents;

[0291] Z 2a Z 3a Z 3b Z 4a Z 4b Z 4c Z 5a Z 5b Z 5c and Z 5d Each can be used independently to represent a single bond and -C(R) B1 -2-, -O-, -CO-, -S-, -SO-, -SO2-, -CONH-, or -NHCO-;

[0292] R B1 Each R can independently represent a hydrogen atom or an alkyl group that can be substituted by a halogen atom, or two R atoms bonded to the same carbon atom. B1 They bond together to form a non-aromatic ring that can have substituents;

[0293] The wavy line indicates the bonding area;

[0294] The wavy lines represent the two bonding sites on the same ring, which are bonded to the two adjacent carbon atoms on that ring.

[0295] In equations (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 can be independently represented as an aromatic ring that may have substituents or a non-aromatic ring that may have substituents. These cyclic structures are preferably aromatic rings that may have substituents, more preferably benzene rings that may have substituents, and even more preferably benzene rings that may be alkyl-substituted.

[0296] A non-aromatic ring refers to a ring other than an aromatic ring that is aromatic as a whole. A non-aromatic ring can be a non-aromatic carbon ring with only carbon atoms as ring-forming atoms, or a non-aromatic heterocycle with heteroatoms such as oxygen, nitrogen, and sulfur atoms as ring-forming atoms in addition to carbon atoms. A non-aromatic ring is preferred. A non-aromatic ring can be a saturated ring or an unsaturated ring. A non-aromatic ring with 3 to 21 members is preferred, a non-aromatic ring with 4 to 17 members is more preferred, and a non-aromatic ring with 5 to 14 members is even more preferred. Suitable examples of non-aromatic rings (non-aromatic carbon rings) include: monocyclic non-aromatic saturated carbon rings such as cyclobutane, cyclopentane, cyclohexane, cycloheptane, and cyclooctane; monocyclic non-aromatic unsaturated carbon rings such as cyclobutene, cyclopentene, cyclohexene, cycloheptene, cyclooctene, cyclopentadiene, and cyclohexadiene; bicyclic [2.2.1]heptane (norbornene), bicyclic [4.4.0]decane (naphthane), bicyclic [5.3.0]decane, bicyclic [4.3.0]nonane (indane), bicyclic [3.2.1]octane, bicyclic [5.4.0]undecane, bicyclic [3.3.0]octane, bicyclic [3.3.1]nonane, and tricyclic [5.2.1.0]octane. 2,6 Decane ring (tetrahydrobicyclopentadiene ring), tricyclic [3.3.1.1] 3,7 Decane ring (adamantane ring), tricyclic [6.2.1.0] 2,7 Non-aromatic saturated carbon rings with a bicyclic system or higher, such as undecane rings; bicyclic [2.2.1]hept-2-ene rings (norbornene rings), bicyclic [2.2.2]oct-2-ene rings, bicyclic [4.4.0]dec-2-ene rings, and other non-aromatic unsaturated carbon rings with a bicyclic system or higher. Non-aromatic rings can be a subset of non-aromatic rings fused with aromatic rings. Examples of non-aromatic rings fused with aromatic rings include: indene rings, indene rings, tetrahydronaphthalene rings, 1,2-dihydronaphthalene rings, 1,4-dihydronaphthalene rings, fluorene rings, 9,10-dihydroanthracene rings, and 9,10-dihydrophenanthrene rings.

[0297] As a 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 55The substituents that can be present are not particularly limited, but examples include: 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 Iodine substituents (here, R) C Each alkyl group is represented independently.

[0298] R C The monovalent hydrocarbon group shown preferably has 1 to 50 carbon atoms, more preferably 1 to 20. R C The monovalent hydrocarbon group shown can be either a monovalent saturated hydrocarbon group or a monovalent unsaturated hydrocarbon group. Additionally, R... C The monovalent hydrocarbon group shown may or may not have an aromatic structure. As R C Examples of monovalent hydrocarbon groups shown include alkyl, alkenyl, aryl, aralkyl, alkylaryl, etc.

[0299] The alkyl group can be straight-chain, branched, or cyclic. The alkyl group preferably has 1 to 14 carbon atoms, more preferably 1 to 10, further 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, isohexyl, octyl, isooctyl, tert-octyl, cyclopentyl, cyclohexyl, and cyclohexylmethyl.

[0300] The alkenyl group can be any of linear, branched, or cyclic. The alkenyl group preferably has 2 to 14 carbon atoms, more preferably 2 to 10, further preferably 2 to 6, and particularly preferably 2 to 3. Examples of alkenyl groups include: vinyl, propenyl (allyl, 1-propenyl, isopropenyl), butenyl (1-butenyl, crotonyl, methylallyl, isocrotonyl, etc.), pentenyl (1-pentenyl, etc.), hexenyl (1-hexenyl, etc.), heptenyl (1-heptenyl, etc.), octenyl (1-octenyl, etc.), cyclopentenyl (2-cyclopentenyl, etc.), and cyclohexenyl (3-cyclohexenyl), etc.

[0301] The aryl group preferably has 6 to 14 carbon atoms, more preferably 6 to 10. Examples of aryl groups include phenyl, 1-naphthyl, and 2-naphthyl.

[0302] The aralkyl group can 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, phenethyl, hydrogenated cinnamyl, α-methylbenzyl, α-isopropylphenyl, 1-naphthylmethyl, 2-naphthylmethyl, etc.

[0303] The alkylaryl group can be an aryl group substituted with one or more (preferably one) alkyl groups. The alkylaryl group preferably has 7 to 15 carbon atoms, 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, 2-isopropylphenyl, etc.

[0304] 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 Each can be used independently to represent a single bond and -C(R) B1 -2-, -O-, -CO-, -S-, -SO-, -SO2-, -CONH-, or -NHCO-, preferably single bonds, -C(R B1 )2- or -O-.

[0305] R B1 Each R can independently represent a hydrogen atom or an alkyl group that can be substituted by a halogen atom, or two R atoms bonded to the same carbon atom. B1 They bond together to form a non-aromatic ring that can have substituents. Alkyl groups can bond with R... C The alkyl groups are the same. R B1 Each of the following is preferred to represent a hydrogen atom or an alkyl group that may be substituted with a halogen atom; more preferably, a hydrogen atom or a methyl group that may be substituted with a halogen atom; further preferably, a hydrogen atom, a methyl group or a trifluoromethyl group; and even more preferably, a hydrogen atom or a methyl group.

[0306] As R B1 The substituents that can be present are not particularly limited, but examples include: halogen atoms, -NO2, -CN, -COH, -OH, -SH, -NH2, -COOH, -R C -COR C -ORC -SR C -SOR C -SO2R C -NHR C -NR C -COOR C -OCOR C -CONH2, -CONHR C -CONR C -NHCOR C Isovalent substituent (R) C (As mentioned above).

[0307] In formula (B1), q1 represents an integer greater than or equal to 0, preferably an integer from 0 to 10, and more preferably 0.

[0308] Examples of aromatic maleimide resins include the maleimide resin represented by formula (B2).

[0309] [Chemical Formula 19]

[0310]

[0311] In formula (B2),

[0312] R B2 Each can be used independently to represent a hydrogen atom or an alkyl group that can be substituted with a halogen atom;

[0313] Ring B 21 Each can be represented independently as an aromatic carbon ring that may have substituents;

[0314] q2 represents an integer greater than or equal to 1;

[0315] The q2 units can be the same or different in each unit.

[0316] In equation (B2), R B2 Each can be used independently to represent a hydrogen atom or an alkyl group that can be substituted with a halogen atom. Alkyl groups can be combined with R... C The alkyl groups are the same. R B2 Each is preferably represented independently by a hydrogen atom or an alkyl group; more preferably by a hydrogen atom or a methyl group; and even more preferably by a hydrogen atom.

[0317] In equation (B2), ring B 21 Each can be represented independently as an aromatic carbide ring that may have substituents. The aromatic carbide ring can be combined with a ring Z-shaped structure. 11 , Ring Z 21 , Ring Z 22 , Ring Z 31 , Ring Z 32 , Ring Z 33 , Ring Z 41 , Ring Z42 , Ring Z 43 , Ring Z 44 , Ring Z 51 , Ring Z 52 , Ring Z 53 , Ring Z 54 and Ring Z 55 The aromatic rings described in the section on aromatic rings are the same as those in the section on aromatic carbon rings. Additionally, ring B... 21 The "substituent" in the text can, for example, interact with the cyclic Z-ring. 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 They can have the same substituents. Ring B 21 Each of the following is preferred to represent a benzene ring that may have substituents; more preferably, a benzene ring that may be substituted by groups selected from alkyl and aryl groups; and even more preferably, an (unsubstituted) benzene ring.

[0318] In formula (B2), q2 represents an integer greater than or equal to 1, preferably an integer from 1 to 10.

[0319] Another example of an aromatic maleimide resin is the maleimide resin represented by the following formula (B3).

[0320] [Chemical Formula 20]

[0321]

[0322] In formula (B3),

[0323] R B3 Each can be used independently to represent a hydrogen atom or an alkyl group that can be substituted with a halogen atom;

[0324] Ring B 31 Ring B 32 and Ring B 33 Each can be represented independently as an aromatic carbon ring that may have substituents;

[0325] q3 represents an integer greater than or equal to 1;

[0326] The q3 units can be the same or different in each unit.

[0327] In formula (B3), RB3 Each can be used independently to represent a hydrogen atom or an alkyl group that can be substituted with a halogen atom. Alkyl groups can be combined with R... C The alkyl groups are the same. R B3 Each of the following 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.

[0328] In equation (B3), ring B 31 Ring B 32 and Ring B 33 Each can be represented independently as an aromatic carbon ring that may have substituents. Ring B 31 Ring B 32 and Ring B 33 The aromatic carbon ring shown can interact with 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 aromatic rings described in the section on aromatic rings are the same as those in the section on aromatic carbon rings. Additionally, ring B... 31 Ring B 32 and Ring B 33 The "substituent" in the text can, for example, interact with the cyclic Z-ring. 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 They can have the same substituents. Ring B 31 Ring B 32 and Ring B 33 Each and every one of them is preferably a benzene ring that may have substituents, more preferably a benzene ring that may be substituted by groups selected from alkyl and aryl groups, and even more preferably an (unsubstituted) benzene ring.

[0329] In formula (B3), q3 represents an integer greater than or equal to 1, preferably an integer from 1 to 10.

[0330] As another example of aromatic maleimide resins, the maleimide resin represented by the following formula (B4) can be cited.

[0331] [Chemical Formula 21]

[0332]

[0333] In equation (B4),

[0334] R B4 Each can be used independently to represent an alkyl group;

[0335] Ring B 41 and Ring B 42 Each can be represented independently as an aromatic carbon ring that may have substituents;

[0336] q4 represents an integer greater than or equal to 1;

[0337] The q4 units can be the same or different in each unit.

[0338] In equation (B4), R B4 Each alkyl group can be represented independently. R B4 Methyl is preferred.

[0339] In equation (B4), ring B 41 Each can be represented independently as an aromatic ring that may have substituents. Additionally, ring B... 41 The "substituent" in the text can, for example, interact with the cyclic Z-ring. 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 They can have the same substituents. Ring B 41 Each and every one of them is preferably a benzene ring that may have substituents, more preferably a benzene ring that may be substituted with an alkyl group, and even more preferably a benzene ring that is substituted with an alkyl group.

[0340] In equation (B4), ring B 42 Each can be represented independently as an aromatic ring that may have substituents. Additionally, ring B... 42 The "substituent" in the text can, for example, interact with the cyclic Z-ring. 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 They can have the same substituents. Ring B 42 Each and every one of them is preferably a benzene ring that may have substituents, more preferably a benzene ring that may be alkyl-substituted, and even more preferably an (unsubstituted) benzene ring.

[0341] In formula (B4), q4 represents an integer greater than or equal to 1, preferably an integer from 1 to 20.

[0342] As another example of aromatic maleimide resins, the maleimide resin represented by the following formula (B5-1) can be cited.

[0343] [Chemical Formula 22]

[0344]

[0345] In equation (B5-1),

[0346] R B51 Each can be used independently to represent an alkylene group;

[0347] R B52 Represents a hydrogen atom or a monovalent hydrocarbon group that may have substituents;

[0348] R B53 Represents a hydrogen atom or a group represented by the following formula (B5-2);

[0349] Ring B 51 and Ring B 52 Each can be represented independently as an aromatic carbon ring that may have substituents;

[0350] q 51 Represents integers greater than or equal to 1;

[0351] q 52 Each can independently represent an integer greater than 1;

[0352] q 51 Each unit can be the same or different in each unit;

[0353] q 52 Each unit can be the same or different within each unit.

[0354] [Chemical Formula 23]

[0355]

[0356] In equation (B5-2),

[0357] The wavy line indicates the bonding area;

[0358] Regarding the other symbols, see above.

[0359] In equation (B5-1), R B51 Each alkylene group is represented independently. R B51 Preferably, it is methylene, ethylene, or ethylidene.

[0360] In equation (B5-1), R B52 Each can independently represent a hydrogen atom or a monovalent hydrocarbon group that may have substituents. As R B52 The monovalent hydrocarbon groups shown can be, for example, monovalent aliphatic groups, monovalent aromatic groups, or monovalent groups composed of combinations thereof.

[0361] In equations (B5-1) and (B5-2), ring B 51 Each can be represented independently as an aromatic carbon ring that may have substituents. Ring B 51 The "substituent" in the text can, for example, interact with the cyclic Z-ring. 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 They can have the same substituents. Ring B 51 Each and every one of the following is preferred to be a benzene ring that may have substituents, more preferably a benzene ring that may be alkyl-substituted, even more preferably an alkyl-substituted benzene ring, even more preferably an alkyl-substituted benzene ring at one ortho position relative to the maleimide group, and even more preferably an ethyl-substituted benzene ring at one ortho position relative to the maleimide group.

[0362] In equation (B5-1), ring B 52 This indicates an aromatic carbon ring that can have substituents. Ring B 52 The "substituent" in the text can, for example, interact with the cyclic Z-ring. 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 They can have the same substituents. Ring B 52 Preferably, it is a benzene ring that may have substituents, and more preferably, it is a benzene ring that may be substituted with alkyl groups.

[0363] In equation (B5-1), q 51 Represents integers greater than or equal to 1. Additionally, q... 52 Each integer can be independently represented as an integer greater than 1, preferably an integer from 1 to 50, more preferably an integer from 1 to 30, and even more preferably an integer from 1 to 15.

[0364] (B) The maleimide equivalent of the 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, and the upper limit is 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 equivalent is the mass of (B) maleimide resin per molar equivalent of maleimide groups.

[0365] (B) The molecular weight of the maleimide resin is preferably less than 5,000, more preferably less than 3,000, and even more preferably less than 2,000, less than 1,500, less than 1,200 or less than 1,000. There is no particular limitation on its lower limit, for example, it can be more than 300, more than 400, more than 500, etc.

[0366] Commercially available maleimide resins include, for example, Shin-Etsu Chemical Industries Co., Ltd.'s "SLK-2600" and "SLK-6895-T90" maleimide resins containing a dimeric diamine structure; and Designer Molecules Inc.'s "BMI-1500," "BMI-1700," "BMI-3000J," "BMI-689," and "BMI-2500" maleimide resins containing a dimeric diamine structure. Aromatic maleimide resins such as "BMI-6100" manufactured by Inc.; biphenyl aryl alkyl maleimide resins such as "MIR-5000-60T", "MIR-3000-70MT", and "MIR-3000-70T" manufactured by Nippon Kayaku Co., Ltd.; "BMI-70" and "BMI-80" manufactured by KI Chemical Co., Ltd.; and "BMI-2300" and "BMI-TMH" manufactured by Daiwa Chemical Industries Co., Ltd. Additionally, maleimide resins (maleimide compounds containing an indene ring skeleton) disclosed in Japanese Inventors Association Publication No. 2020-500211 can be used as maleimide resins.

[0367] Furthermore, the maleimide resin represented by formula (B5-1) can be synthesized by known synthetic methods, or commercially available products can be used. For example, a known synthetic method can be described in Synthesis Example 1 of Japanese Patent Application Publication No. 2024-102755. Additionally, the maleimide resin represented by formula (B5-1) can also be a maleimide resin manufactured through the following steps (1) and (2).

[0368] Step (1): A step in which an aromatic amine compound represented by formula (b1) is reacted with a compound having a benzyl ether skeleton under a solid acid catalyst.

[0369] Step (2): A step of condensing the intermediate amine compound generated in step (1) with maleic anhydride.

[0370] [Chemical Formula 24]

[0371]

[0372] In equation (b1),

[0373] R b1 Hydrocarbon groups representing 1 to 18 carbon atoms;

[0374] R b2 and R b3 Each can be independently represented by a hydrogen atom or a hydrocarbon group with 1 to 18 carbon atoms;

[0375] Rb4 and R b5 Each can be independently represented by an alkyl group having 1 to 6 hydrogen atoms or carbon atoms.

[0376] In the resin composition according to the first embodiment, from the viewpoint of better exerting the desired effect of the present invention, the content of component (B) in the resin composition is preferably 1% by mass or more, more preferably 3% by mass or more, and even more preferably 5% by mass or more, 5.5% by mass or more, 6.5% by mass or more, 7% by mass or more, 8% by mass or more, 10% by mass or more, 11% by mass or more, 12% by mass or more, or 13% by mass or more, relative to the non-volatile components in 100% by mass of the resin composition. In one embodiment, the content of component (B) in the resin composition may be 14% by mass or more, 16% by mass or more, 18% by mass or more, 20% by mass or more, or 21% by mass or more, relative to the non-volatile components in 100% by mass of the resin composition.

[0377] From the viewpoint of maximizing the desired effects of the present invention, the upper limit of the content of component (B) in the resin composition relative to the non-volatile components in 100% by mass of the resin composition is preferably 35% by mass or less, more preferably 30% by mass or less, and even more preferably 25% by mass or less, 23% by mass or less, or 21% by mass or less. In one embodiment, the upper limit of the content of component (B) in the resin composition relative to the non-volatile components in 100% by mass of the resin composition may be 20% by mass or less, 18% by mass or less, 16% by mass or less, or 14% by mass or less.

[0378] In the resin composition according to the first embodiment, from the viewpoint of better exerting the desired effect of the present invention, the content of component (B) in the resin composition is preferably 10% by mass or more, more preferably 15% by mass or more, and even more preferably 20% by mass or more, 25% by mass or more, 35% by mass or more, or 40% by mass or more, relative to the resin component in 100% by mass of the resin composition. In one embodiment, the content of component (B) in the resin composition may be 48% by mass or more, 50% by mass or more, 60% by mass or more, 65% by mass or more, 70% by mass or more, 71% by mass or more, or 75% by mass or more, relative to the resin component in 100% by mass of the resin composition.

[0379] From the viewpoint of maximizing the desired effects of the present invention, the upper limit of the content of component (B) in the resin composition relative to the resin component in 100% by mass of the resin composition is preferably 85% by mass or less, more preferably 75% by mass or less, and even more preferably 71% by mass or less, 70% by mass or less, 65% by mass or less, 60% by mass or less, 50% by mass or less, or 48% by mass or less. In one embodiment, the upper limit of the content of component (B) in the resin composition relative to the resin component in 100% by mass of the resin composition may be 40% by mass or less, 35% by mass or less, 25% by mass or less, or 20% by mass or less.

[0380] Relative to the non-volatile components in 100% by mass of the resin composition, when the content of component (A-1) is set as M... A1 [mass %], set the content of component (B) as M. B When [mass %], the mass ratio of component (A-1) to component (B) (content of component (A-1) / content of component (B)) can be determined by M. A1 / M B Indicated. From the viewpoints of the heat resistance, mechanical strength, surface roughness after decontamination treatment, and adhesion to the conductor layer of the cured resin composition, the mass ratio M A1 / M B Preferably, it is 0.1 or more, more preferably 0.2 or more, and even more preferably 0.3 or more, 0.5 or more, 0.8 or more, or 1 or more. In the mass ratio M... A1 / M B When the lower limit is above the aforementioned lower limit value, the cured material with a small surface roughness (arithmetic mean roughness of the cured material surface) after the cleaning treatment is more suitable.

[0381] From the viewpoint of the mechanical strength of the cured resin composition and its adhesion to the conductor layer, the mass ratio M A1 / M B The upper limit is preferably 5 or less, more preferably 4 or less, and even more preferably 3 or less, 2 or less, or 1.5 or less.

[0382] <(C) Phosphorus-based flame retardants>

[0383] The resin composition according to the first embodiment of the present invention includes (C) a phosphorus-based flame retardant as component (C). The (C) phosphorus-based flame retardant may be used alone or in combination of two or more.

[0384] Examples of phosphorus-based flame retardants (C) include phosphazene compounds, phosphates, phosphate esters, polyphosphates, phosphonates, phosphonates, phosphonates, and phosphonates. Among these, from the viewpoint of significantly obtaining the effects of the present invention, any one of phosphazene compounds and compounds having a phosphaphenanthrene structure is more preferred as component (C).

[0385] (C) Component (C) is more preferably any one of the compounds represented by formula (C-1) and formula (C-2) below. The compound represented by formula (C-1) below includes a compound having a phosphaphenanthrene structure. The compound represented by formula (C-2) below is a phosphazene compound.

[0386] [Chemical Formula 25]

[0387]

[0388] In equation (C-1), R 1c and R 2c Each independently represents an alkyl, alkoxy, aryl, aryloxy, or cross-linking functional group, R 3c R represents a cross-linking functional group, a divalent hydrocarbon group, a monovalent hydrocarbon group, or a monovalent group composed of combinations thereof. 1c and R 2c They can bond together to form a ring.

[0389] In equation (C-2), R 11c and R 12c Each of these groups independently represents a hydrogen atom, a hydroxyl group, or an alkyl or cross-linked functional group having 1 to 6 carbon atoms. n1 represents an integer from 3 to 25, m1 represents an integer from 1 to 5, and m2 represents an integer from 0 to 5.

[0390] As an alkyl group, alkyl groups having 1 to 20 carbon atoms are preferred, alkyl groups having 1 to 15 carbon atoms are more preferred, alkyl groups having 1 to 10 carbon atoms, alkyl groups having 1 to 6 carbon atoms, or alkyl groups having 1 to 3 carbon atoms are even more preferred. This number of carbon atoms does not include the number of carbon atoms in the substituents described later. The alkyl group can be straight-chain, branched, or cyclic. Examples of alkyl groups include: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, isopropyl, sec-butyl, tert-butyl, etc. Among these, methyl and ethyl are preferred, and ethyl is more preferred.

[0391] As an alkoxy group, an alkoxy group having 1 to 20 carbon atoms is preferred, an alkoxy group having 1 to 15 carbon atoms is more preferred, and an alkoxy group having 1 to 10 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or an alkoxy group having 1 to 3 carbon atoms is even more preferred. This number of carbon atoms does not include the number of carbon atoms in the substituents described later. The alkoxy group can be linear, branched, or cyclic. Examples of alkoxy groups include: methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy, 2-butoxy, tert-butoxy, 1-pentoxy, 2-pentoxy, 3-pentoxy, 2,2-dimethylpropoxy, 2-ethylpropoxy, 3,3-dimethylpropoxy, 1,1-dimethylpropoxy, cyclopentoxy, 1-hexoxy, 2-hexoxy, 3-hexoxy, 4-methylpentoxy, etc. Among these, methoxy and ethoxy are preferred as alkoxy groups, and ethoxy is more preferred.

[0392] As an aryl group, an aryl group with 6 to 20 carbon atoms is preferred, an aryl group with 6 to 15 carbon atoms is more preferred, and an aryl group with 6 to 10 carbon atoms is even more preferred. This number of carbon atoms does not include the number of carbon atoms in the substituents described later. Examples of aryl groups include phenyl and naphthyl groups. Among these, phenyl is preferred.

[0393] As an aryloxy group, an aryloxy group having 6 to 20 carbon atoms is preferred, an aryloxy group having 6 to 15 carbon atoms is more preferred, and an aryloxy group having 6 to 10 carbon atoms is even more preferred. This number of carbon atoms does not include the number of carbon atoms of the substituents described later. Examples of aryloxy groups include phenoxy, 4-methylphenoxy, 3-methylphenoxy, 2-methylphenoxy, 2,6-dimethylphenoxy, 2,4-dimethylphenoxy, 2,3-dimethylphenoxy, 2,4,6-trimethylphenoxy, 4-isopropylphenoxy, 2-isopropylphenoxy, 3-isopropylphenoxy, 4-isobutylphenoxy, 2-isobutylphenoxy, 3-isobutylphenoxy, 4-tert-butylphenoxy, 2-tert-butylphenoxy, 3-tert-butylphenoxy, 2,6-di-tert-butylphenoxy, 2,4-di-tert-butylphenoxy, 2,3-di-tert-butylphenoxy, 2-methyl-4-tert-butylphenoxy, 2-methyl-6-tert-butylphenoxy, and 4-methyl-2-tert-butylphenoxy. Among these, phenoxy is preferred as the aryloxy group.

[0394] R 1c and R 2c The alkyl, alkoxy, aryl, and aryl groups represented may have substituents. There are no particular limitations on substituents; examples include halogen atoms, -OC atoms, etc. 1-6 Alkyl, -N(C) 1-10 Alkyl)2, C 1-10 Alkyl, C 6-10 Aryl, -NH2, -CN, -C(O)OC 1-10Alkyl groups, -COOH, -C(O)H, -NO2, etc. Additionally, substituents can be cross-linking functional groups. Here, the term "C" is used... p-q "(p and q are positive integers, satisfying p < q) indicates that the number of carbon atoms in the organic group immediately following the term is p to q. For example, "C 1-10 The term "alkyl" refers to an alkyl group having 1 to 10 carbon atoms. These substituents can bond with each other to form a ring, and the ring structure includes spirocyclic or fused rings.

[0395] The above-mentioned substituents may further have substituents (hereinafter, sometimes referred to as "secondary substituents"). As secondary substituents, the same substituents as the above-mentioned substituents may be used unless otherwise specified.

[0396] R 1c and R 2c They can bond together to form a ring. R 1c and R 2c The ring structures that can be formed include spirocyclic and fused ring structures. Examples of ring structures include groups represented by the following formula (C-1a). In formula (C-1a), * indicates the site bonded to a phosphorus atom.

[0397] [Chemical Formula 26]

[0398]

[0399] In equation (C-1), R 3c It represents a cross-linking functional group, a divalent hydrocarbon group, a monovalent hydrocarbon group, or a monovalent group composed of combinations thereof.

[0400] The monovalent hydrocarbon group preferably has 1 to 20 carbon atoms, more preferably 1 to 15 carbon atoms, and even more preferably 1 to 10 carbon atoms or 1 to 6 carbon atoms. This number of carbon atoms does not include the number of carbon atoms in the substituents. The monovalent hydrocarbon group can be any of the following: linear, branched, or cyclic. Examples of monovalent hydrocarbon groups include: monovalent aliphatic hydrocarbon groups and monovalent aromatic hydrocarbon groups, with monovalent aromatic hydrocarbon groups being preferred. The monovalent hydrocarbon group can be any of the following: monovalent saturated hydrocarbon groups and monovalent unsaturated hydrocarbon groups, with monovalent unsaturated hydrocarbon groups being preferred. Specific examples of monovalent hydrocarbon groups include: alkyl, alkenyl, aryl, etc. Regarding alkyl and aryl groups, the relationship with R in formula (B-1) is... 1 The alkyl and aryl groups represented are the same.

[0401] Examples of alkenyl groups include ethynyl, propynyl, butynyl, and pentyynyl.

[0402] A monovalent hydrocarbon group may have substituents. The substituents are related to R in formula (C-1). 1c The substituents that can be present are the same. Among them, the substituents that the monovalent hydrocarbon group can have are preferably crosslinking functional groups, and more preferably hydroxyl groups.

[0403] The divalent hydrocarbon group preferably has 1 to 20 carbon atoms, more preferably 1 to 15 carbon atoms, and even more preferably 1 to 10 or 1 to 6 carbon atoms. The divalent hydrocarbon group can be any of straight-chain, branched, or cyclic. Examples of divalent hydrocarbon groups include divalent aliphatic hydrocarbon groups and divalent aromatic hydrocarbon groups, with divalent aliphatic hydrocarbon groups being preferred. The divalent hydrocarbon group can be any of divalent saturated hydrocarbon groups and divalent unsaturated hydrocarbon groups, with divalent saturated hydrocarbon groups being preferred. Specific examples of divalent hydrocarbon groups include alkylene groups, alkenyl groups, and arylene groups.

[0404] Examples of alkylene compounds include methylene, ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene, and decylene, with methylene being preferred.

[0405] Examples of alkenyl groups include: vinylene, propenylene, butenylene, pentenylene, hexenylene, heptenylene, octenylene, nonenylene, decenylene, etc.

[0406] Examples of aryl groups include phenylene and naphthylene.

[0407] The divalent hydrocarbon group can have substituents. The substituents are related to R in formula (B-1). 1 The substituents that can be present are the same. Among them, the substituents that the divalent hydrocarbon group can have are preferably crosslinking functional groups, and more preferably hydroxyl groups.

[0408] As a monovalent group composed of combinations thereof, a monovalent group composed of a monovalent hydrocarbon group and a crosslinking functional group is preferred; a monovalent group composed of a crosslinking functional group, a monovalent hydrocarbon group and an oxygen atom is preferred; and a monovalent group composed of a divalent hydrocarbon group and a crosslinking functional group is preferred, more preferably any one of a monovalent group composed of a monovalent hydrocarbon group and a crosslinking functional group, and a monovalent group composed of a divalent hydrocarbon group and a crosslinking functional group.

[0409] Specific examples of monovalent groups formed by combinations of these can be seen in the groups represented by the following formulas (Ca) to (Cb). In these formulas, * indicates the site bonded to a phosphorus atom.

[0410] [Chemical Formula 27]

[0411]

[0412] The compound represented by formula (C-1) is preferably a compound with a phosphenanthrene structure represented by formula (C-1-1).

[0413] [Chemical Formula 28]

[0414]

[0415] In equation (C-1-1), R 21c It represents a cross-linking functional group, a divalent hydrocarbon group, a monovalent hydrocarbon group, or a monovalent group composed of combinations thereof.

[0416] In equation (C-1-1), R 31c The term represents a cross-linking functional group, a divalent hydrocarbon group, a monovalent hydrocarbon group, or a monovalent group composed of combinations thereof, and is related to R in formula (C-1). 3c same.

[0417] Examples of compounds represented by formula (C-1) include, but are not limited to, compounds (C1) to (C6) listed below. In the formula, Et represents the ethyl group.

[0418] [Chemical Formula 29]

[0419]

[0420] In equation (C-2), R 11c Crosslinking functional groups are represented independently, as described above.

[0421] In equation (C-2), R 12c Each of these can independently represent a hydrogen atom, a hydroxyl group, or an alkyl group. Alkyl groups are related to R in formula (C-1). 1c The alkyl groups represented are the same.

[0422] In formula (C-2), n1 represents an integer from 3 to 25, preferably an integer from 3 to 15, more preferably an integer from 3 to 10, and even more preferably 3.

[0423] In formula (C-2), m1 represents an integer from 1 to 5, preferably an integer from 1 to 3, and more preferably 1.

[0424] In formula (C-2), m2 represents an integer from 0 to 5, preferably an integer from 0 to 3, and more preferably 0 or 1.

[0425] Examples of compounds represented by formula (C-2) include, but are not limited to, compounds such as (C7) exemplified below.

[0426] [Chemical Formula 30]

[0427]

[0428] (C) Commercially available products may be used as ingredients. Examples of commercially available products include: "HCA-HQ-HST" manufactured by Sanko Co., Ltd.; "FP-72TP", "FP-700", and "FP-100" manufactured by Fushimi Pharmaceutical Co., Ltd.; and "V5", "V7", "API-09", "MC-2", and "MC-4" manufactured by Katayama Chemical Co., Ltd.

[0429] From the viewpoint of improving flame retardancy, when the resin component in the resin composition layer is set to 100% by mass, the phosphorus atom content is preferably 0.01% by mass or more, more preferably 0.02% by mass or more, and even more preferably 0.03% by mass or more. The upper limit is preferably 0.5% by mass or less, more preferably 0.4% by mass or less, and even more preferably 0.3% by mass or less. Here, "phosphorus atom content" refers to the concept of including the phosphorus atom content contained in components (A) to (F), excluding component (C), in addition to the phosphorus atom content contained in component (C).

[0430] In the resin composition according to the first embodiment, from the viewpoint of better exerting the desired effect of the present invention, the content of component (C) in the resin composition relative to 100% by mass of the non-volatile components of the resin composition layer is preferably 0.01% by mass or more, more preferably 0.05% by mass or more, and even more preferably 0.1% by mass or more or 0.2% by mass or more. In one embodiment, the content of component (C) in the resin composition relative to 100% by mass of the non-volatile components of the resin composition layer may be 0.3% by mass or more, 0.4% by mass or more, 0.5% by mass or more, 0.8% by mass or more, or 1% by mass or more.

[0431] From the viewpoint of maximizing the desired effect of the present invention, the upper limit of the content of component (C) in the resin composition relative to the non-volatile components in 100% by mass of the resin composition is preferably 3% by mass or less, more preferably 1.5% by mass or less, and even more preferably 1.2% by mass or less, 1% by mass or less, 0.8% by mass or less, 0.5% by mass or less, 0.4% by mass or less, and 0.3% by mass or less.

[0432] In the resin composition according to the first embodiment, from the viewpoint of achieving the desired effect of the present invention, the content of component (C) in the resin composition is preferably 0.03% by mass or more, more preferably 0.15% by mass or more, and even more preferably 0.3% by mass or more, 0.5% by mass or more, 0.7% by mass or more, or 0.9% by mass or more, relative to the resin composition in 100% by mass of the resin composition layer. In one embodiment, the content of component (C) in the resin composition may be 1.1% by mass or more, 1.3% by mass or more, 1.5% by mass or more, 2% by mass or more, 2.5% by mass or more, or 3% by mass or more, relative to the resin composition in 100% by mass of the resin composition layer.

[0433] From the viewpoint of maximizing the desired effects of the present invention, the upper limit of the content of component (C) in the resin composition relative to the resin component in 100% by mass of the resin composition is preferably 10% by mass or less, more preferably 5% by mass or less, and even more preferably less than 5% by mass, 4% by mass or less, 3.5% by mass or less, 3% by mass or less, 2.5% by mass or less, 2% by mass or less, or 1.5% by mass or less. It should be noted that, in one embodiment, the content of component (C) in the resin composition relative to the resin component in 100% by mass of the resin composition may be 1.3% by mass or less, 1.1% by mass or less, 0.9% by mass or less, 0.7% by mass or less, or 0.5% by mass or less.

[0434] Relative to the non-volatile components in 100% by mass of the resin composition, when the content of component (A-1) is set as M... A1 [mass %], set the content of component (C) as M. C When [mass %], the mass ratio of component (C) to component (A-1) (content of component (C) / content of component (A-1)) can be determined by M C / M A1 This indicates that, from the viewpoint of better achieving the desired effects of the invention, the mass ratio M... C / M A1 Preferably, it is 0.01 or higher, more preferably 0.02 or higher, and even more preferably 0.025 or higher. Mass ratio M C / M A1 The upper limit is preferably 0.1 or less, more preferably 0.08 or less, and even more preferably 0.06 or less, 0.04 or less, or 0.03 or less.

[0435] Relative to the non-volatile components in 100% by mass of the resin composition, when the content of component (B) is set as M... B [mass %], set the content of component (C) as M. C When [mass %], the mass ratio of component (C) to component (B) (content of component (C) / content of component (B)) can be determined by M. C / M B This indicates that, from the viewpoint of better achieving the desired effects of the invention, the mass ratio M... C / M B The mass ratio M is 0.01 or higher, more preferably 0.02 or higher, and even more preferably 0.025 or higher. C / M B The upper limit is preferably 0.1 or less, more preferably 0.08 or less, and even more preferably 0.06 or less, 0.04 or less, or 0.03 or less.

[0436] <(D) Inorganic filler materials>

[0437] The resin composition involved in this embodiment includes an inorganic filler as component (D). (D) The inorganic filler is particulate inorganic material. (D) The inorganic filler is contained in the resin composition in particulate form, and is typically contained in the cured product in a particulate state.

[0438] Examples of inorganic filler materials for (D) 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 suitable, and silica is particularly suitable. Therefore, the inorganic filler material for (D) preferably contains silica, but may contain only silica. Examples of silica include: amorphous silica, fused silica, crystalline silica, synthetic silica, and hollow silica. Furthermore, spherical silica is preferred as silica. (D) Inorganic filler materials can be used alone or in combination of two or more.

[0439] Commercially available products as (D) inorganic filler materials include: "SP60-05" and "SP507-05" manufactured by Nippon Steel Chemical Materials Co., Ltd.; "YC100C", "YA050C", "YA050C-MJE", "YA010C", "SC2500SQ", "SO-C4", "SO-C2", and "SO-C1" manufactured by Admatechs Co., Ltd.; "UFP-30", "DAW-03", and "FB-105FD" manufactured by DENKA Co., Ltd.; "SILFIL NSS-3N", "SILFIL NSS-4N", and "SILFIL NSS-5N" manufactured by Tokuyama Co., Ltd.; "CellSpheres" and "MGH-005" manufactured by Pacific Cement Co., Ltd.; and "LHP-208" manufactured by UBE EXSYMO Co., Ltd., etc.

[0440] (D) The average particle size of the inorganic filler material is preferably 0.01 μm or more, more preferably 0.05 μm or more, and even more preferably 0.1 μm or more. In one embodiment, the lower limit of the average particle size of the inorganic filler material may be 0.2 μm or more or 0.3 μm or more.

[0441] The upper limit of the average particle size of the inorganic filler is preferably 10 μm or less, more preferably 5 μm or less, even more preferably 3 μm or less, and even more preferably 1 μm or less, 0.7 μm or less, or 0.5 μm or less. It should be noted that the average particle size of the inorganic filler can be 0.4 μm or less or 0.3 μm or less.

[0442] (D) The average particle size of inorganic filler materials can be determined by laser diffraction / scattering based on the Mie scattering theory. Specifically, a laser diffraction-scattering particle size distribution measuring device can be used to prepare the particle size distribution of the inorganic filler material on a volume basis, and the median particle size can be used as the average particle size for measurement. The sample for testing can be prepared by weighing 100 mg of inorganic filler material and 10 g of methyl ethyl ketone into a tubular bottle and dispersing it ultrasonically for 10 minutes. For the sample to be tested, a laser diffraction-scattering particle size distribution measuring device is used, with the light source wavelength set to blue and red, and the volume-based particle size distribution of the inorganic filler material is measured in a flow cell manner. The average particle size, as the median particle size, can be calculated from the obtained particle size distribution. Examples of laser diffraction-scattering particle size distribution measuring devices include the "LA-960" manufactured by Horiba Seisakusho Co., Ltd.

[0443] (D) The specific surface area of ​​the inorganic filler material is preferably 0.1 m². 2 / g or more, preferably 0.5m 2 / g or more, further preferably 1m 2 / g or more, especially preferably 3m 2 / g or more, preferably 100m 2 / g or less, preferably 70m 2 / g or less, more preferably 50m 2 / g or less, especially preferably 40m 2 / g or less. (D) The specific surface area of ​​inorganic filler materials can be obtained by the following method: according to the BET method, using a specific surface area measuring device (Macsorb HM-1210 manufactured by Mountech), nitrogen gas is adsorbed onto the sample surface, and the specific surface area is calculated using the BET multi-point method.

[0444] From the perspective of improving moisture resistance and dispersibility, (D) inorganic filler materials are preferably treated with surface treatment agents. Examples of surface treatment agents include: fluorinated silane coupling agents, aminosilane coupling agents, epoxysilane coupling agents, mercaptosilane coupling agents, silane coupling agents, alkoxysilanes, organosilazane compounds, titanate coupling agents, etc. A single surface treatment agent can be used, or two or more can be used in any combination.

[0445] Commercially available surface treatment agents include, for example: KBM403 (3-epoxypropoxypropyltrimethoxysilane) manufactured by Shin-Etsu Chemical Industry Co., Ltd.; KBM803 (3-mercaptopropyltrimethoxysilane) manufactured by Shin-Etsu Chemical Industry Co., Ltd.; KBE903 (3-aminopropyltriethoxysilane) manufactured by Shin-Etsu Chemical Industry Co., Ltd.; KBM573 (N-phenyl-3-aminopropyltrimethoxysilane) manufactured by Shin-Etsu Chemical Industry Co., Ltd.; SZ-31 (hexamethyldisilazane) manufactured by Shin-Etsu Chemical Industry Co., Ltd.; KBM103 (phenyltrimethoxysilane) manufactured by Shin-Etsu Chemical Industry Co., Ltd.; KBM-4803 (long-chain epoxy silane coupling agent) manufactured by Shin-Etsu Chemical Industry Co., Ltd.; and KBM-7103 (3,3,3-trifluoropropyltrimethoxysilane) manufactured by Shin-Etsu Chemical Industry Co., Ltd.

[0446] From the viewpoint of improving the dispersibility of inorganic filler materials, the degree of surface treatment by surface treatment agent is preferably limited to a specified range. Specifically, 100% by mass of inorganic filler material is preferably surface treated with 0.2% to 5% by mass of surface treatment agent, more preferably with 0.2% to 3% by mass of surface treatment agent, and even more preferably with 0.3% to 2% by mass of surface treatment agent.

[0447] The degree of surface treatment by the surface treatment agent can be evaluated by the carbon content per unit surface area of ​​the inorganic filler. From the viewpoint of improving the dispersibility of the inorganic filler, the carbon content per unit surface area of ​​the inorganic filler is preferably 0.02 mg / m². 2 More preferably 0.1 mg / m 2 The above is further optimized to 0.2 mg / m². 2 That's all. On the other hand, from the viewpoint of preventing an increase in the melt viscosity of the resin composition layer, 1.0 mg / m³ is preferred. 2 Below, 0.8 mg / m² is more preferred. 2 The following is a further preferred dosage: 0.5 mg / m² 2 the following.

[0448] The carbon content per unit surface area of ​​the inorganic filler material (D) can be determined after washing the surface-treated inorganic filler material with a solvent (e.g., methyl ethyl ketone (MEK)). Specifically, a sufficient amount of MEK as a solvent is added to the surface-treated inorganic filler material, and ultrasonic washing is performed at 25°C for 5 minutes. After removing the supernatant and drying the solid components, the carbon content per unit surface area of ​​the inorganic filler material can be determined using a carbon analyzer. A carbon analyzer such as the "EMIA-320V" manufactured by Horiba Seisakusho Co., Ltd. can be used.

[0449] (D) The inorganic filler material may include (D1) hollow inorganic filler material as component (D1), and may also include (D2) solid inorganic filler material as component (D2). In this specification, (D1) hollow inorganic filler material refers to an inorganic filler material having pores within the particles. Conversely, in this specification, (D2) solid inorganic filler material refers to an inorganic filler material that substantially does not have voids or pores, including cases where voids are unavoidably incorporated during the manufacture of solid inorganic filler material. In the resin composition of the present invention, (D) inorganic filler material may consist only of (D1) hollow inorganic filler material, may consist only of (D2) solid inorganic filler material, or may consist of a combination of (D1) hollow inorganic filler material and (D2) solid inorganic filler material in any ratio.

[0450] (D1) Hollow inorganic filler materials have pores inside the particles. (D1) Hollow inorganic filler materials can be single hollow particles with only one pore inside the particle, or multi-hollow particles with two or more pores inside the particle, or a mixture of single hollow particles and multi-hollow particles. (D1) Hollow inorganic filler materials can be used alone, or two or more can be combined in any ratio.

[0451] The average porosity P (volume %) of the hollow inorganic filler material (D1) is, for example, 30 vol% or more, preferably 40 vol% or more, more preferably 45 vol% or more, and even more preferably 50 vol% or more. In one embodiment, the lower limit of the average porosity P of the hollow inorganic filler material (D1) may be 55 vol% or more, 60 vol% or more, 65 vol% or more, 70 vol% or more, 75 vol% or more, or 80 vol% or more. The upper limit of the average porosity P of the hollow inorganic filler material (D1) is preferably 95 vol% or less, more preferably 90 vol% or less, and even more preferably 85 vol% or less.

[0452] The average porosity P (volume %) of inorganic filler materials is defined as the volume ratio of the total volume of one or more pores present inside the particles to the volume of the entire particle relative to its outer surface (total pore volume / particle volume), for example, using the measured value D of the actual density (apparent density) of the inorganic filler material. M (g / cm 3 The theoretical value D of the material density of the inorganic filler material. T (g / cm 3 ), which can be calculated using the following formula (I).

[0453] [Mathematical Expression 1]

[0454]

[0455] The actual density (apparent density) of inorganic filler materials can be measured, for example, using a true density measuring device. Examples of true density measuring devices include the ULTRAPYCNOMETER 1000 manufactured by QUANTACHROME. Nitrogen gas can be used as the measuring gas, for example.

[0456] As the material for the hollow inorganic filler in (D1), the same inorganic compound as the material for the inorganic filler in (D) can be used. Alternatively, an inorganic composite oxide can be used as the material for the hollow inorganic filler in (D1). An inorganic composite oxide is an oxide containing two or more atoms selected from metal atoms and half-metal atoms. As such an inorganic composite oxide, an oxide containing silicon and a combination of one or more atoms selected from metal atoms and half-metal atoms other than silicon is preferred. Examples of metal atoms combined with silicon include: aluminum, lead, nickel, cobalt, copper, zinc, zirconium, iron, lithium, magnesium, barium, potassium, calcium, titanium, boron, sodium, etc., with aluminum being preferred. Therefore, as an inorganic composite oxide, an oxide containing silicon and aluminum is preferred, and aluminum silicate is more preferred.

[0457] (D1) Hollow inorganic filler materials can be commercially available or manufactured by known or similar methods. A method for manufacturing hollow silica, as an example of (D1) hollow inorganic filler materials, can be, for example, by a method comprising the following steps: preparing an aqueous solution containing a pore-forming substance and an alkaline compound; mixing and stirring the aqueous solution with an alkoxysilane to precipitate silica particles; removing the pore-forming substance from the silica particles to obtain a hollow silica precursor; and calcining the hollow silica precursor.

[0458] (D1) The surface of the hollow inorganic filler material can be heat-treated. There are no particular limitations on the conditions for surface heat treatment. From the viewpoint of suppressing fracture (cracking) caused by collision between particles, the treatment temperature is, for example, in the range of 50°C to 100°C, preferably 70°C to 80°C, and the treatment time is, for example, in the range of 0.5 hours to 3 hours, preferably 1 hour to 3 hours.

[0459] As described above, (D2) solid inorganic filler material is an inorganic filler material that is substantially free of voids or pores. The average porosity P (volume%) of (D2) solid inorganic filler material can, for example, be less than 0.5 volume%. The average porosity P (volume%) of (D2) solid inorganic filler material can be calculated by the above formula (I).

[0460] In the resin composition according to the first embodiment, from the viewpoint of better exerting the desired effect of the present invention, the content of component (D) in the resin composition is preferably 50% by mass or more, more preferably 60% by mass or more, and even more preferably 65% ​​by mass or more, relative to the non-volatile components in 100% by mass of the resin composition. In one embodiment, the content of component (D) in the resin composition may be 68% by mass or more, 70% by mass or more, 71% by mass or more, or 72% by mass or more, relative to the non-volatile components in 100% by mass of the resin composition. From the viewpoint of better exerting the desired effect of the present invention, the upper limit of the content of component (D) in the resin composition is preferably 90% by mass or less, more preferably 85% by mass or less, and even more preferably 80% by mass or less or 75% by mass or less, relative to the non-volatile components in 100% by mass of the resin composition. Alternatively, it may be 72% by mass or less, 71% by mass or less, 70% by mass or less, 68% by mass or less, or 65% by mass or less.

[0461] Relative to the non-volatile components in 100% by mass of the resin composition, when the content of component (B) is set as M... B [mass %], set the content of component (D) as M. D When [mass %], the mass ratio of component (B) to component (D) (content of component (B) / content of component (D)) can be obtained from M. B / M D Indicated. From the viewpoint of the heat resistance, mechanical strength, and adhesion to the conductor layer of the cured resin composition, the mass ratio M B / M D Preferably, it is 0.05 or more, more preferably 0.08 or more, and even more preferably 0.12 or more, 0.15 or more, 0.18 or more, 0.2 or more, 0.23 or more, or 0.25 or more. In one embodiment, the mass ratio M B / M D The lower limit can be above 0.26, above 0.28, above 0.30, above 0.32, above 0.34, above 0.36, above 0.38, or above 0.40.

[0462] From the viewpoint of the heat resistance of the cured resin composition and the surface roughness after cleaning treatment, the mass ratio M B / M D The upper limit is preferably 1 or less, more preferably 0.7 or less, and even more preferably 0.5 or less or 0.4 or less. In one embodiment, the mass ratio M B / M DThe upper limit can be below 0.38, below 0.36, below 0.34, below 0.32, below 0.30, below 0.28, below 0.26, below 0.25, below 0.23, or below 0.2.

[0463] Relative to the non-volatile components in 100% by mass of the resin composition, when the content of component (C) is set as M C [mass %], set the content of component (D) as M. D When [mass %], the mass ratio of component (C) to component (D) (content of component (C) / content of component (D)) can be determined by M. C / M D This indicates that, from the viewpoint of better achieving the desired effects of the invention, the mass ratio M... C / M D The lower limit is preferably 0.001 or more, more preferably 0.002 or more, and even more preferably 0.003 or more, 0.004 or more, or 0.005 or more.

[0464] mass ratio M C / M D The upper limit is preferably 0.02 or less, more preferably 0.015 or less, and even more preferably 0.01 or less, 0.008 or less, or 0.007 or less.

[0465] <(E) Thermoplastic Resins>

[0466] The resin composition according to the first embodiment of the present invention may include (E) thermoplastic resin as an optional component. Unless otherwise stated, the thermoplastic resin as component (E) does not include substances equivalent to components (A-1) to (D) described above. The thermoplastic resin (E) may be compatible with resin components other than thermoplastic resin (E) and may be included in the resin composition. When the resin composition according to the first embodiment includes component (E), one type of thermoplastic resin (E) may be used alone, or two or more types may be used in combination.

[0467] Examples of thermoplastic resins (E) include: polyimide resins, phenoxy resins, polystyrene resins, polyvinyl acetal resins, polyolefin resins, polybutadiene resins, polyamide-imide resins, polyether-imide resins, polysulfone resins, polyethersulfone resins, polyphenylene ether resins, polycarbonate resins, polyetheretherketone resins, polyester resins, etc. Preferably, the thermoplastic resin (E) includes at least one selected from polyimide resins, phenoxy resins, and polystyrene resins.

[0468] Polyimide resins can be resins having an imide structure. Polyimide resins are generally obtained through an imidization reaction of a diamine compound with an acid anhydride, or an imidization reaction of a diisocyanate compound with an acid anhydride. Specific examples of polyimide resins include linear polyimides (the polyimide described in Japanese Patent Application Publication No. 2006-37083) obtained by reacting difunctional hydroxyl-terminated polybutadiene, a diisocyanate compound, and a tetrabasic acid anhydride, and modified polyimides such as polyimides containing a polysiloxane backbone (the polyimides described in Japanese Patent Application Publication Nos. 2002-12667 and 2000-319386, etc.). Commercially available polyimide resins can also be used, such as "RIKACOAT SN20" and "RIKACOAT PN20" manufactured by Shin Nippon Rika Co., Ltd. Polyimide resins can be used alone or in combination of two or more.

[0469] In a suitable embodiment, the polyimide resin comprises a structural unit represented by the following formula (E1) (hereinafter also referred to as "structural unit (E1)"). The number of structural units (E1) contained in each molecule of polyimide resin is 1 or more, without particular limitation, and may be 100 or less, 50 or less, or 30 or less.

[0470] [Chemical Formula 31]

[0471]

[0472] In formula (E1),

[0473] R E1 This represents the tetravalent group represented by the following formula (E2-1).

[0474] R E2 This represents the divalent group represented by the following formula (E2-2).

[0475] [Chemical Formula 32]

[0476]

[0477] In equation (E2-1),

[0478] Ar E11 Ar E12 Ar E13 and Ar E14 Each aromatic ring, which may have substituents, is represented independently.

[0479] L E11 L E12 and L E13 Each of these groups represents a divalent linker independently.

[0480] nE1 Represents integers greater than or equal to 0.

[0481] The wavy line indicates the bonding area.

[0482] [Chemical Formula 33]

[0483]

[0484] In equation (E2-2),

[0485] Ar E21 Ar E22 Ar E23 and Ar E24 Each aromatic ring, which may have substituents, is represented independently.

[0486] L E21 L E22 and L E23 Each of these independently represents a divalent linker group.

[0487] n E2 Represents integers greater than or equal to 1.

[0488] The wavy line indicates the bonding area.

[0489] In equation (E2-1), Ar E11 Ar E12 Ar E13 and Ar E14 Each aromatic ring can be represented independently as having substituents. Ar E11 Ar E12 Ar E13 and Ar E14 The aromatic ring represented (hereinafter also referred to as "aromatic ring F") is preferably an aromatic ring with 6 to 100 carbon atoms, more preferably an aromatic ring with 6 to 50 carbon atoms, and even more preferably an aromatic carbon ring with 6 to 100 carbon atoms, and even more preferably an aromatic carbon ring with 6 to 50 carbon atoms.

[0490] As Ar E11 Ar E12 Ar E13 and Ar E14 Examples of aromatic rings represented include: benzene rings, furan rings, thiophene rings, pyrrole rings, and pyrazole rings. azole ring, iso- Monocyclic aromatic rings such as azole rings, thiazole rings, imidazole rings, pyridine rings, pyridazine rings, pyrimidine rings, and pyrazine rings; naphthalene rings, anthracene rings, benzofuran rings, isobenzofuran rings, indole rings, isoindole rings, benzothiophene rings, benzimidazole rings, indazole rings, and benzo[…]. azole ring, benzyl isocyanate Fused rings are those formed by the fusion of two or more monocyclic aromatic rings, such as azole rings, benzothiazole rings, quinoline rings, isoquinoline rings, quinoxaline rings, acridine rings, quinazoline rings, cyclophosphine rings, and phthalazine rings; fused rings are those formed by the fusion of one or more monocyclic non-aromatic rings onto one or more monocyclic aromatic rings, such as indanthium rings, fluorene rings, and tetrahydronaphthalene rings. E11 Ar E12 Ar E13 and Ar E14 The aromatic rings represented are each preferably aromatic carbon rings with 6 to 14 carbon atoms that may have substituents, and more preferably benzene rings.

[0491] In equation (E2-1), in Ar E11 Ar E12 Ar E13 and Ar E14 In the case of an aromatic ring having substituents, the number of substituents is not limited. Such substituents (hereinafter also referred to as "substituent S") can be independently categorized as follows: halogen atom, alkyl, cycloalkyl, alkoxy, cycloalkoxy, aryl, aryloxy, aralkyl, arylalkoxy, monovalent heterocyclic group, alkylene group, amino, silyl, acyl, acyloxy, carboxyl, sulfonyl, cyano, nitro, hydroxyl, mercapto, and oxo.

[0492] In equation (E2-1), L E11 L E12 and L E13 Each represents a divalent linker independently. L F11 L F12 and L F13 The divalent linking group is preferably a divalent group composed of one or more (e.g., 1 to 3000, 1 to 1000, 1 to 100, or 1 to 50) skeletal atoms selected from carbon, oxygen, nitrogen, sulfur, and silicon atoms. Examples of divalent linking groups include: -SO2-, -CO-, -COO-, -O-, -S-, -O-C6H4-O- (where -C6H4- represents phenylene), -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, alkenylene, ynylene, arylene, heteroarylene, -C(=O)-, -C(=O)-O-, -NR 0 -(Here, R) 0 (representing hydrogen atoms, alkyl groups with 1 to 3 carbon atoms) and -C(=O)-NR 0 -

[0493] As LE11 L E12 and L E13 The alkylene group preferably has 1 to 10 carbon atoms, more preferably 1 to 6, and even more preferably 1 to 5 or 1 to 4. As L E11 L E12 and L F13 The number of carbon atoms in the alkenyl group is preferably 2 to 10, more preferably 2 to 6, and even more preferably 2 to 5. As L E11 L E12 and L E13 The arylene group preferably has 6 to 20 carbon atoms, more preferably 6 to 10. As L E11 L E12 and L E13 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.

[0494] L E11 L E12 and L E13 The divalent linker group represented preferably does not contain an aromatic ring. In one embodiment, L E11 The divalent linking group and L are represented E13 The divalent linking groups represented are identical to each other, L E11 The divalent linking group and L are represented E12 The divalent linking groups represented are different from each other. In a suitable embodiment, L E11 and L E13 It is -O-, and L E12 It is an alkylene group that may have substituents. In a more suitable embodiment, L E11 and L E13 It is -O-, and L E12 It is a dimethylmethylene group.

[0495] In equation (E2-1), n E1 Represents an integer greater than or equal to 0. In a suitable implementation, n E1 Represents an integer greater than or equal to 1. For n... E1 There is no particular limit to the upper limit of the integer represented; for example, it can be set to 50, 40, 30, or 20.

[0496] Of the four valent groups represented by formula (E2-1), L is preferred. E11 and L E13 It is -O-, and L E12 It can be an alkylene group that may have substituents. Furthermore, Ar is more preferred. E11 Ar E12 Ar E13 and Ar E14Each is an aromatic carbon ring with 6 to 14 carbon atoms that can have substituents, L E11 and L E13 It is -O-, and L E12 It is an alkylene group that can have substituents. Furthermore, Ar is preferred. E11 Ar E12 Ar E13 and Ar E14 Each is an aromatic carbon ring with 6 to 14 carbon atoms that can have substituents, L E11 and L E13 It is -O-, and L E12 It is a dimethylmethylene group.

[0497] In equation (E2-2), Ar E21 Ar E22 Ar E23 and Ar E24 Each aromatic ring can be represented independently as having substituents. Ar E21 Ar E22 Ar E23 and Ar E24 The examples of the aromatic ring and the substituents that the aromatic ring may have are the same as those of the aromatic ring F and substituent S described above. Therefore, in a suitable embodiment, Ar E21 Ar E22 Ar E23 and Ar E24 Each is an aromatic carbon ring with 6 to 14 carbon atoms that can have substituents.

[0498] In equation (E2-2), L E21 L E22 and L E23 Each represents a divalent linker independently. L E21 L E22 and L E23 Examples of divalent linking groups represented are similar to L. E11 L E12 and L E13 The divalent linking group represented is the same. Therefore, in a suitable embodiment, L E21 and L F23 For -O-, L E22 In a more suitable embodiment, L is an alkylene group that may have substituents. E21 and L E23 For -O-, L E22 It is a dimethylmethylene group.

[0499] In equation (E2-2), n E2 Represents an integer greater than or equal to 1. In a suitable implementation, n E2Represents integers greater than or equal to 2. For n... E2 There is no particular limit to the upper limit of the integer represented; for example, it can be set to 60, 50, 40, or 30.

[0500] Of the divalent groups represented by formula (E2-2), L is preferred. E21 and L E23 It is -O-, and L E22 It can be an alkylene group that may have substituents. Furthermore, Ar is more preferred. E21 Ar E22 Ar E23 and Ar F24 Each is an aromatic carbon ring with 6 to 14 carbon atoms that can have substituents, L E21 and L E23 It is -O-, and L E22 It is an alkylene group that can have substituents. Furthermore, Ar is preferred. E21 Ar E22 Ar E23 and Ar F24 Each is an aromatic carbon ring with 6 to 14 carbon atoms that can have substituents, L E21 and L E23 It is -O-, and L E22 It is a dimethylmethylene group.

[0501] Of the tetravalent group represented by formula (E2-1) and the divalent group represented by formula (E2-2), Ar is preferred. E11 Ar E12 Ar E13 and Ar E14 Each is an aromatic carbon ring with 6 to 14 carbon atoms that can have substituents, and Ar E21 Ar E22 Ar E23 and Ar E24 Each is an aromatic carbon ring with 6 to 14 carbon atoms, which may each have substituents. Furthermore, L is preferred. E11 and L E13 For -O-, L E12 For alkylene groups that may have substituents, L E21 and L E23 It is -O-, and L E22 It is an alkylene group that may have substituents.

[0502] The aforementioned structural unit (E1) can be obtained, for example, by a known method for manufacturing polyimide resins, typically by polymerizing a monomer composition containing a tetracarboxylic dianhydride and a diamine compound to imide, or by polymerizing a monomer composition containing a tetracarboxylic dianhydride and a diisocyanate compound to imide. It should be noted that polyimide resins may contain a portion of polyamic acid structures that can be generated during the imideation process.

[0503] The structural unit (E1) can be obtained, for example, by reacting 2,2-bis[4-(3,4-dicarboxyphenoxy)phenyl]propane dianhydride (the compound represented by formula (E3-1) below; hereinafter also referred to as "BPADA") with 4,4'-[1,4-phenylenebis[(1-methylethoxy)-4,1-phenyleneoxy]]bisaniline (the compound represented by formula (E3-2) below; hereinafter also referred to as "BPPAN"). That is, in one embodiment, R in the structural unit (E1) E1 The skeleton is from BPADA, and R E2 The skeleton is derived from BPPAN.

[0504] [Chemical Formula 34]

[0505]

[0506] Furthermore, the polyimide resin may further comprise structural units represented by the following formula (E4) (hereinafter also referred to as "structural units (E4)"). Therefore, in one embodiment, the polyimide resin further comprises structural units represented by the following formula (E4). The number of structural units (E4) contained in each molecule of polyimide resin is 0 or more, without particular limitation, and may be set to 100 or less, 50 or less, or 30 or less.

[0507] [Chemical Formula 35]

[0508]

[0509] In formula (E4),

[0510] R E3 This indicates a tetravalent aliphatic group that may have substituents or a tetravalent aromatic group that may have substituents;

[0511] R E4 This indicates a divalent aliphatic group that may have substituents or a divalent aromatic group that may have substituents. Wherein, in R... E3 With R E1 Under the same conditions, R E4 With R E2 Different, in R E4 With R E2 Under the same conditions, R E3With R E1 different.

[0512] In equation (E4), R E3 This indicates a tetravalent aliphatic group that may have substituents or a tetravalent aromatic group that may have substituents.

[0513] R E3 The tetravalent aliphatic group represented contains at least a carbon atom, and is preferably a tetravalent group composed of one or more (e.g., 1 to 3000, 1 to 1000, 1 to 100, or 1 to 50) skeletal atoms selected from carbon, oxygen, nitrogen, sulfur, and silicon atoms. R E3 The tetravalent aliphatic group represented is more preferably a tetravalent aliphatic group with 1 to 100 carbon atoms, and more preferably 1 to 50 carbon atoms. In formula (E4), in R E3 In the case of a tetravalent aliphatic group having a substituent, the examples of the substituent are the same as the examples of the substituent S.

[0514] R E3 The tetravalent aromatic group represented is preferably a tetravalent aromatic group with 6 to 100 carbon atoms, more preferably 6 to 50 carbon atoms. The aromatic group contains at least an aromatic ring. Examples of aromatic rings contained in the aromatic group are Ar in formula (E2-1). E11 Ar E12 Ar E13 and Ar E14 The examples of aromatic rings represented are the same. In equation (E4), in R... E3 In the case of a tetravalent aromatic group having a substituent, the examples of the substituent are the same as the examples of the substituent S.

[0515] As R E3 The tetravalent aromatic group represented can be exemplified by the group obtained by removing two 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'-benzophenone tetracarboxylic dianhydride, and 3,3',4,4'-diphenylsulfone tetracarboxylic dianhydride.

[0516] In equation (E4), R E4 This indicates a divalent aliphatic group that may have substituents or a divalent aromatic group that may have substituents.

[0517] R E4The divalent aliphatic group represented here contains at least a carbon atom, and is preferably a divalent group composed of one or more (e.g., 1 to 3000, 1 to 1000, 1 to 100, or 1 to 50) skeletal atoms selected from carbon, oxygen, nitrogen, sulfur, and silicon atoms. In formula (F4), R E4 The divalent aliphatic group represented is more preferably a divalent aliphatic group with 1 to 100 carbon atoms, and even more preferably 1 to 50 carbon atoms.

[0518] In equation (E4), in R E4 When representing a divalent aliphatic group with a substituent, examples of such substituent are the same as examples of substituent S, for example, alkyl groups having 1 to 6 carbon atoms. Therefore, in one embodiment, R... F4 It is a divalent aliphatic group that can have substituents, one of which is an alkyl group having 1 to 6 carbon atoms. Additionally, in one embodiment, R... E4 It is a divalent aliphatic group that may have substituents, and is a divalent group obtained by removing two amino groups from isophorone diamine.

[0519] In R E4 In the case of a divalent aliphatic group that may have substituents, it can be a group obtained by removing two amino groups from a diamine compound having a straight-chain aliphatic group that 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.

[0520] In R E4 In the case of a divalent aliphatic group that may have substituents, it may be a group obtained by removing two amino groups from a diamine compound 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 that has a branched aliphatic group that may have substituents.

[0521] In R E4 In the case of a divalent aliphatic group that may have substituents, it may be selected from 5-amino-1,3,3-trimethylcyclohexanemethylamine (isophorone diamine), 1,4-diaminocyclohexane, 1,3-diaminocyclohexane, 1,4-cyclohexane bis(methylamine), 1,3-cyclohexane bis(methylamine), 4,4'-diaminodicyclohexylmethane, bis(4-amino-3-methylcyclohexyl)methane, 3(4),8(9)-bis(aminomethyl)tricyclo[5.2.1.0] 2,6[2.2.1]Heptane, 1,3-diaminoadamantane, 3,3'-diamino-1,1'-diadamantane, and 1,6-diaminoadamantane are diamine compounds having aliphatic groups that may have substituents, after removing two amino groups. These diamine compounds are characterized in that their aliphatic groups contain alicyclic carbocyclic rings.

[0522] R E4 The divalent aromatic group represented is preferably a divalent aromatic group with 6 to 100 carbon atoms, more preferably 6 to 50 carbon atoms. The aromatic group contains at least an aromatic ring. Examples of aromatic rings contained in the aromatic group are the same as those of aromatic ring E. In formula (E4), in R... E4 In the case of a divalent aromatic group having a substituent, the examples of the substituent are the same as the examples of the substituent S.

[0523] In R E4 In the case of a divalent aromatic group that may have substituents, it may be a group obtained by removing two amino groups from a diamine compound having an aromatic group that may have substituents, selected from 4,4'-diaminodiphenyl ether, 1,4-phenylenediamine, and 2,2-bis[4-(4-aminophenoxy)phenyl]propane.

[0524] Among them, in R E3 With R E1 Under the same conditions, R E4 With R E2 Different, in R E4 With R E2 Under the same conditions, R E3 With R E1 Different. In one implementation, R E3 With R E1 same.

[0525] The aforementioned structural unit (E4) can be obtained, for example, according to known methods for manufacturing polyimide resins. Structural unit (E4) can be obtained, for example, by reacting BPADA with isophorone diamine. That is, in one embodiment, R in the structural unit (E4) E3 The skeleton is from BPADA, and R E4 The backbone is derived from isophorone diamine. In R E3 With R E1 In the same case, in one implementation, R E3 and R E1 The skeleton is from BPADA.

[0526] There are no particular limitations on the end structure of polyimide resins. For example, the end structure of polyimide resins can be an anhydride group, carboxyl group, or amino group derived from its raw material compounds (e.g., acids such as BPADA, amine compounds such as BPPAN).

[0527] The glass transition temperature (Tg) of the 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, and it can be set to 300°C or lower, etc. The glass transition temperature (Tg) of the polyimide resin can be determined by thermomechanical analysis (TMA).

[0528] The content of structural unit (E1) 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 percentage 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 percentage (mass percentage) of the structural unit (E1) can be calculated based on the proportion of each material added (parts by mass) in the synthesis of the polyimide resin. Alternatively, the molecular weight of the polyimide resin and the formula weight of the structural unit (E1) can be specified as the ratio of the formula weight of the structural unit (E1) to the molecular weight. When the polyimide resin is a polymer, the content percentage of the structural unit (E1) estimated from the degree of polymerization is preferably within the aforementioned range.

[0529] The content of the structural unit (E4) in the polyimide resin can be 0% by mass (i.e., without structural unit (E4)), and there is no upper limit to this as long as it does not inhibit the effect of the present invention. When the polyimide resin is a resin that further contains the structural unit (F4), the content of the structural unit (E4) in the polyimide resin can be, for example, set to 1% or more by mass, 5% or more by mass, 10% or more by mass, 20% or more by mass, or 30% or more by mass, and 95% or less by mass, 90% or less by mass, 80% or less by mass, 70% or less by mass, or 60% or less by mass. Here, the content of the structural unit (E4) is calculated in the same way as the content of the structural unit (E1).

[0530] 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, further 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 converted from polystyrene as determined by gel permeation chromatography (GPC).

[0531] Examples of phenoxy resins include those having one or more skeletons selected from the following: bisphenol A skeleton, bisphenol F skeleton, bisphenol S skeleton, bisphenol acetophenone skeleton, phenolic varnish skeleton, biphenyl skeleton, fluorene skeleton, dicyclopentadiene skeleton, norbornene skeleton, naphthalene skeleton, anthracene skeleton, adamantane skeleton, terpene skeleton, and trimethylcyclohexane skeleton. The terminal group of the phenoxy resin can be any functional group such as a phenolic hydroxyl group or a phenoxy group. Specific examples of phenoxy resins include: Mitsubishi Chemical's "1256" and "4250" (both phenoxy resins containing a bisphenol A backbone); Mitsubishi Chemical's "YX8100" (phenoxy resin containing a bisphenol S backbone); Mitsubishi Chemical's "YX6954" (phenoxy resin containing a bisphenol acetophenone backbone); Nippon Steel Chemical Materials Co., Ltd.'s "FX280" and "FX293"; and Mitsubishi Chemical's "YL7500BH30," "YX6954BH30," "YX7553," "YX7553BH30," "YL7769BH30," "YL6794," "YL7213," "YL7290," "YL7482," "YL7891BH30," and "YX7891T30," etc. Phenoxy resins can be used alone or in combination of two or more types.

[0532] Specific examples of polystyrene resins include: Asahi Kasei Corporation's "H1041", "Tuftec H1043", "Tuftec P2000", "Tuftec MP10" (hydrogenated styrene-based thermoplastic elastomer), "Tuftec N503M" (carboxyl-modified styrene-based elastomer), "Tuftec N501" (amino-modified styrene-based elastomer), and "Tuftec M1913" (anhydride-modified styrene-based elastomer); Daicel Corporation's "EPOFRIENDAT 501" and "CT310" (epoxidized styrene-butadiene thermoplastic elastomer); and Kuraray Corporation's "SEPTON HG252" (hydroxyl-modified styrene-based elastomer) and "SEPTON S8104" (unmodified styrene-based elastomer). Polystyrene resins can be used alone or in combination of two or more types.

[0533] Examples of polyvinyl acetal resins include polyvinyl formal resin and polyvinyl butyral resin, with polyvinyl butyral resin being preferred. Specific examples of polyvinyl acetal resins include the S-LEC BH series, BX series (e.g., BX-5Z), KS series (e.g., KS-1), BL series, and BM series manufactured by Sekisui Chemicals Co., Ltd. A single polyvinyl acetal resin can be used alone, or two or more can be used in combination.

[0534] Examples of polyolefin resins include: low-density polyethylene, ultra-low-density polyethylene, high-density polyethylene, ethylene-vinyl acetate copolymer, ethylene-ethyl acrylate copolymer, ethylene-methyl acrylate copolymer, and other ethylene-based copolymers; polyolefin polymers such as polypropylene and ethylene-propylene block copolymers. A single polyolefin resin can be used alone, or two or more can be used in combination.

[0535] Examples of polybutadiene resins include: resins containing a hydrogenated polybutadiene backbone, hydroxyl-containing polybutadiene resins, phenolic hydroxyl-containing polybutadiene resins, carboxyl-containing polybutadiene resins, acid anhydride-containing polybutadiene resins, epoxy-containing polybutadiene resins, isocyanate-containing polybutadiene resins, urethane-containing polybutadiene resins, and polyphenylene ether-polybutadiene resins. Polybutadiene resins can be used alone or in combination of two or more types.

[0536] Specific examples of polyamide-imide resins include "VYLOMAX HR11NN" and "VYLOMAX HR16NN" manufactured by Toyobo Co., Ltd. Other examples include modified polyamide-imide resins such as "KS9100" and "KS9300" (polyamide-imide containing a polysiloxane backbone) manufactured by Resonac Co., Ltd. Polyamide-imide resins can be used alone or in combination of two or more types.

[0537] Specific examples of polysulfone resins include polysulfones "P1700" and "P3500" manufactured by Solvay Advanced Polymers. Polysulfone resins can be used alone or in combination of two or more types.

[0538] 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 Co., Ltd. Specific examples of polyetherimide resins include "ULTEM" manufactured by GE Co., Ltd.

[0539] Examples of polycarbonate resins include: hydroxyl-containing carbonate resins, phenolic hydroxyl-containing carbonate resins, carboxyl-containing carbonate resins, anhydride-containing carbonate resins, isocyanate-containing carbonate resins, and urethane-containing carbonate resins. Specific examples of polycarbonate resins include: "FPC0220" manufactured by Mitsubishi Gas Chemical Co., Ltd.; "T6002" and "T6001" (polycarbonate diol) manufactured by Asahi Kasei Corporation; and "C-1090," "C-2090," and "C-3090" (polycarbonate diol) manufactured by Kuraray Co., Ltd. Polycarbonate resins can be used alone or in combination of two or more types.

[0540] Specific examples of polyetheretherketone resins include "SUMIPLOYK" manufactured by Sumitomo Chemical Co., Ltd.

[0541] Examples of polyester resins include: polyethylene terephthalate resin, polyethylene naphthalate resin, polybutylene terephthalate resin, polybutylene naphthalate resin, polypropylene terephthalate resin, polypropylene naphthalate resin, and polycyclohexanediol terephthalate resin. A single polyester resin can be used alone, or two or more can be used in combination.

[0542] When the resin composition according to the first embodiment includes a thermoplastic resin other than a polyimide resin, the weight-average molecular weight (Mw) of the thermoplastic resin other than the polyimide resin is preferably 5,000 or more, more preferably 8,000 or more, further 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 further preferably 80,000 or less, or 60,000 or less. The weight-average molecular weight of the thermoplastic resin other than the polyimide resin is the weight-average molecular weight of polystyrene as determined by gel permeation chromatography (GPC).

[0543] When the resin composition according to the first embodiment contains (E) thermoplastic resin, the content of component (E) in the resin composition relative to the non-volatile components in 100% by mass of the resin composition is, for example, 0.01% by mass or more, preferably 0.1% by mass or more, more preferably 0.5% by mass or more, and even more preferably 0.9% by mass or more. In one embodiment, the lower limit of the content of component (E) in the resin composition relative to the non-volatile components in 100% by mass of the resin composition may be 1% by mass or more.

[0544] The upper limit of the content of component (E) in the resin composition relative to the non-volatile components in 100% by mass of the resin composition is preferably 10% by mass or less, more preferably 5% by mass or less, and even more preferably 3% by mass or less or 2% by mass or less. In one embodiment, the upper limit of the content of component (E) in the resin composition relative to the non-volatile components in 100% by mass of the resin composition may be 1.5% by mass or less, 1.2% by mass or less, or 1% by mass or less.

[0545] When the resin composition according to the first embodiment contains (E) thermoplastic resin, the content of component (E) in the resin composition is, for example, 0.05% by mass or more, preferably 0.5% by mass or more, more preferably 2.5% by mass or more, and even more preferably 3% by mass or more, relative to the resin component in 100% by mass of the resin composition. In one embodiment, the lower limit of the content of component (E) in the resin composition relative to the resin component in 100% by mass of the resin composition may be 3.2% by mass or more.

[0546] The upper limit of the content of component (E) in the resin composition relative to the resin component in 100% by mass is preferably 15% by mass or less, more preferably 10% by mass or less, and even more preferably 5% by mass or less or 4% by mass or less. In one embodiment, the upper limit of the content of component (E) in the resin composition relative to the resin component in 100% by mass may be 3.6% by mass or less, 3.4% by mass or less, or 3.2% by mass or less.

[0547] <(F) Curing Accelerator>

[0548] The resin composition according to the first embodiment of the present invention may include (F) a curing accelerator as an optional component. Unless otherwise stated, the (F) curing accelerator, as component (F), does not include substances equivalent to components (A-1) to (E) described above. The (F) curing accelerator can promote the curing of the resin composition. One type of (F) curing accelerator may be used alone, or two or more may be used in combination.

[0549] 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. Additionally, thermal free radical polymerization initiators such as peroxide-based free radical polymerization initiators and azo-based free radical polymerization initiators can be used as curing accelerators. Preferably, the curing accelerator (F) includes at least one of imidazole-based curing accelerators, phosphorus-based curing accelerators, peroxide-based free radical polymerization initiators, and azo-based free radical polymerization initiators; more preferably, it includes at least one of imidazole-based curing accelerators and phosphorus-based curing accelerators.

[0550] Examples of imidazole-based curing accelerators include: 2-methylimidazolium, 2-undecylimidazolium, 2-heptadecylimidazolium, 1,2-dimethylimidazolium, 2-ethyl-4-methylimidazolium, 1,2-dimethylimidazolium, 2-ethyl-4-methylimidazolium, 2-phenylimidazolium, 2-phenyl-4-methylimidazolium, 1-benzyl-2-methylimidazolium, 1-benzyl-2-phenylimidazolium, 1-cyanoethyl-2-methylimidazolium, 1-cyanoethyl-2-undecylimidazolium, 1-cyanoethyl-2-ethyl-4-methylimidazolium, 1-cyanoethyl-2-phenylimidazolium, 1-cyanoethyl-2-undecylimidazolium trimellitate, 1-cyanoethyl-2-phenylimidazolium trimellitate, 2,4-diamino-6-[2'-methylimidazolyl-(1')]-ethyl-triazine ... -[2'-undecylimidazolyl-(1')]-ethyl-triazine, 2,4-diamino-6-[2'-ethyl-4'-methylimidazolyl-(1')]-ethyl-triazine, 2,4-diamino-6-[2'-methylimidazolyl-(1')]-ethyl-triazine isocyanuric acid adduct, 2-phenylimidazolyl isocyanuric acid adduct, 2-phenyl-4,5-dihydroxymethylimidazolium, 2-phenyl-4-methyl-5-hydroxymethylimidazolium, 2,3-dihydro-1H-pyrrolo[1,2-a]benzimidazole, 1-dodecyl-2-methyl-3-benzylimidazolium chloride, 2-methylimidazoline, 2-phenylimidazoline and other imidazole compounds and adducts of imidazole compounds with epoxy resins, preferably 2-ethyl-4-methylimidazolium, 2-phenyl-4-methylimidazolium, and 1-benzyl-2-phenylimidazolium. As imidazole-based curing accelerators, commercially available products can be used, such as: "P200-H50" manufactured by Mitsubishi Chemical Corporation; "CUREZOL 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", etc. manufactured by Shikoku Chemical Industry Co., Ltd.

[0551] Examples of phosphorus-based curing accelerators include phosphonium salts and phosphine. Examples of phosphonium salts include: tetrabutylphosphonium bromide, tetrabutylphosphonium chloride, tetrabutylphosphonium acetate, tetrabutylphosphonium decanoate, tetrabutylphosphonium laurate, n-butylphosphonium tetraphenylborate, bis(tetrabutylphosphonium)pyromellitic phthalate, tetrabutylphosphonium hexahydrophthalate, tetrabutylphosphonium 2,6-bis[(2-hydroxy-5-methylphenyl)methyl]-4-methylphenol, di-tert-butylmethylphosphonium tetraphenylborate, and other aliphatic phosphonium salts; methyltriphenylphosphonium bromide... Aromatic phosphonium salts, including ethyltriphenylphosphonium bromide, propyltriphenylphosphonium bromide, butyltriphenylphosphonium bromide, benzyltriphenylphosphonium chloride, tetraphenylphosphonium bromide, p-tolyltriphenylphosphonium tetra-tolylborate, tetraphenylphosphonium tetraphenylborate, tetraphenylphosphonium tetra-tolylborate, triphenylethylphosphonium tetraphenylborate, tri(3-methylphenyl)ethylphosphonium tetraphenylborate, tri(2-methoxyphenyl)ethylphosphonium tetraphenylborate, (4-methylphenyl)triphenylphosphonium thiocyanate, tetraphenylphosphonium thiocyanate, and butyltriphenylphosphonium thiocyanate.

[0552] Examples of phosphine species include: tributylphosphine, tri-tert-butylphosphine, trioctylphosphine, di-tert-butyl(2-butenyl)phosphine, di-tert-butyl(3-methyl-2-butenyl)phosphine, tricyclohexylphosphine, etc.; aliphatic phosphines such as dibutylphenylphosphine, di-tert-butylphenylphosphine, methyl diphenylphosphine, ethyl diphenylphosphine, butyl diphenylphosphine, diphenylcyclohexylphosphine, triphenylphosphine, tri-o-tolylphosphine, tri-m-tolylphosphine, tri-p-tolylphosphine, tri(4-ethylphenyl)phosphine, tri(4-propylphenyl)phosphine, tri(4-isopropylphenyl)phosphine, tri(4-butylphenyl)phosphine, tri(4-tert-butylphenyl)phosphine, tri(2,4-dimethylphenyl)phosphine, tri(2,5-dimethylphenyl)phosphine, tri(2,6-dimethylphenyl)phosphine, etc. Aromatic phosphines such as (3,5-dimethylphenyl)phosphine, tris(2,4,6-trimethylphenyl)phosphine, tris(2,6-dimethyl-4-ethoxyphenyl)phosphine, tris(2-methoxyphenyl)phosphine, tris(4-methoxyphenyl)phosphine, tris(4-ethoxyphenyl)phosphine, tris(4-tert-butoxyphenyl)phosphine, diphenyl-2-pyridylphosphine, 1,2-bis(diphenylphosphino)ethane, 1,3-bis(diphenylphosphino)propane, 1,4-bis(diphenylphosphino)butane, 1,2-bis(diphenylphosphino)acetylene, and 2,2'-bis(diphenylphosphino)diphenyl ether; aromatic phosphine-borane complexes such as triphenylphosphine-triphenylborane; and aromatic phosphine-quinone addition reactants such as triphenylphosphine-p-benzoquinone addition reactants.

[0553] As a phosphorus-based curing accelerator, commercially available products can be used, such as "TBP-DA" manufactured by Beixing Chemical Industry Co., Ltd.

[0554] 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 can be used, such as "PN-50", "PN-23", and "MY-25" manufactured by Ajinomoto Fine-Techno.

[0555] Examples of guanidine-based curing accelerators include: dicyandiamide, 1-methylguanidine, 1-ethylguanidine, 1-cyclohexylguanidine, 1-phenylguanidine, 1-o-tolylguanidine, dimethylguanidine, diphenylguanidine, trimethylguanidine, tetramethylguanidine, pentamethylguanidine, 1,5,7-triazabicyclo[4.4.0]dec-5-ene, 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene, 1-methylbiguanidine, 1-ethylbiguanidine, 1-n-butylbiguanidine, 1-n-octadecylbiguanidine, 1,1-dimethylbiguanidine, 1,1-diethylbiguanidine, 1-cyclohexylbiguanidine, 1-allylbiguanidine, 1-phenylbiguanidine, 1-o-tolylbiguanidine, etc., with dicyandiamide and 1,5,7-triazabicyclo[4.4.0]dec-5-ene being preferred.

[0556] Examples of metal-based curing accelerators include organometallic complexes or organometallic salts of metals such as cobalt, copper, zinc, iron, nickel, manganese, and tin. Specific examples of organometallic complexes include organocobalt complexes such as cobalt(II) and cobalt(III) acetylacetone, organocopper complexes such as copper(II) acetylacetone, organozinc complexes such as zinc(II) acetylacetone, organoiron complexes such as iron(III) acetylacetone, organonickel complexes such as nickel(II) acetylacetone, and organomanganese complexes such as manganese(II) acetylacetone. Examples of organometallic salts include zinc octoate, tin octoate, zinc naphthenate, cobalt naphthenate, tin stearate, and zinc stearate.

[0557] Examples of urea-based curing accelerators include: 1,1-dimethylurea; aliphatic dimethylureas such as 1,1,3-trimethylurea, 3-ethyl-1,1-dimethylurea, 3-cyclohexyl-1,1-dimethylurea, and 3-cyclooctyl-1,1-dimethylurea; and 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 include 1-dimethylurea, 3-(4-isopropylphenyl)-1,1-dimethylurea, 3-(4-methoxyphenyl)-1,1-dimethylurea, 3-(4-nitrophenyl)-1,1-dimethylurea, 3-[4-(4-methoxyphenoxy)phenyl]-1,1-dimethylurea, 3-[4-(4-chlorophenoxy)phenyl]-1,1-dimethylurea, 3-[3-(trifluoromethyl)phenyl]-1,1-dimethylurea, N,N-(1,4-phenylene)bis(N',N'-dimethylurea), and N,N-(4-methyl-1,3-phenylene)bis(N',N'-dimethylurea)[toluenebisdimethylurea], etc.

[0558] Examples of peroxide-based free radical polymerization initiators include: hydrogen peroxide compounds such as 1,1,3,3-tetramethylbutyl hydroperoxide; dialkyl peroxide compounds such as tert-butyl cumene peroxide, di-tert-butyl peroxide, di-tert-hexyl peroxide, di-tert-pentyl peroxide, dicumyl peroxide, 1,4-bis(1-tert-butylperoxy-1-methylethyl)benzene, and 2,5-dimethyl-2,5-bis(tert-butylperoxy)hexane; and dilauroyl peroxide, didecanoyl peroxide, dicyclohexyl peroxide, and dicyclohexyl peroxide. (4-tert-butylcyclohexyl) ester and other peroxide diacyl compounds; peroxide ester compounds such as tert-butyl peracetate, tert-butyl peroxybenzoate, tert-butyl peroxyisopropyl monocarbonate, tert-butyl peroxy-2-ethylhexanoate, tert-butyl peroxyneodecanate, tert-hexyl peroxyisopropyl monocarbonate, tert-butyl peroxylaurate, 1,1-dimethylpropyl 2-ethylperoxyhexanoate, tert-butyl 2-ethylperoxyhexanoate, tert-butyl 3,5,5-trimethylperoxyhexanoate, tert-butyl peroxy-2-ethylhexyl monocarbonate, and tert-butyl peroxymaleate.

[0559] Examples of azo radical polymerization initiators include: 2,2'-azobis(4-methoxy-2,4-dimethylpentanonitrile), 2,2'-azobis(2,4-dimethylpentanonitrile), 2,2'-azobisisobutyronitrile, 2,2'-azobis(2-methylbutyronitrile), 1,1'-azobis(cyclohexane-1-carboxynitrile), 1-[(1-cyano-1-methylethyl)azo]formamide, 2-phenylazo-4-methoxy-2,4-dimethylpentanonitrile, and other azo nitrile compounds; 2,2'-azobis[2-methyl-N-[1,1-bis(hydroxymethyl)-2-hydroxyethyl]propionamide], ... Azoamide compounds such as [(hydroxymethyl)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), 2,2'-azobis(N-cyclohexyl-2-methylpropionamide); alkyl azo compounds such as 2,2'-azobis(2,4,4-trimethylpentane) and 2,2'-azobis(2-methylpropane).

[0560] When the resin composition according to the first embodiment contains a (F) curing accelerator, the content of the (F) component in the resin composition relative to the non-volatile components in 100% by mass of the resin composition is, for example, 0.01% by mass or more, 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 5% by mass or less, more preferably 1% by mass or less, even more preferably 0.5% by mass or less or 0.4% by mass or less.

[0561] When the resin composition according to the first embodiment contains a curing accelerator (F), the content of the (F) component in the resin composition is, for example, 0.05% by mass or more, preferably 0.5% by mass or more, more preferably 1.0% by mass or more, further preferably 1.2% by mass or more, preferably 10% by mass or less, more preferably 5% by mass or less, and further preferably 3% by mass or less, 2% by mass or less, or 1.3% by mass or less.

[0562] In a particularly suitable embodiment, when the total of components (A) and (B) is set to 100% by mass, the content of component (F) is preferably 0.1% by mass or more, more preferably 0.5% by mass or more, even more preferably 1% by mass or more, preferably 5% by mass or less, more preferably 3% by mass or less, and even more preferably 2% by mass or less.

[0563] <(G) Liquid thermosetting resin>

[0564] The resin composition according to the first embodiment of the present invention may optionally include (G) liquid thermosetting resin as component (G). Unless otherwise stated, the liquid thermosetting resin as component (G) does not include substances equivalent to components (A-1) to (C) described above. The (G) liquid thermosetting resin is liquid at 25°C. In addition, the (G) liquid thermosetting resin can form bonds and cure through a thermal reaction. Therefore, by curing the resin composition comprising (A-1) a compound containing a first specific structural unit and a specific terminal group, (B) maleimide resin, (C) a phosphorus flame retardant, (D) an inorganic filler, and (G) liquid thermosetting resin, an insulating layer comprising the cured resin composition can be obtained. The (G) liquid thermosetting resin may be used alone or in combination of two or more.

[0565] From the viewpoint of maximizing the desired effects of the present invention, (G) the liquid thermosetting resin preferably contains a cyclic structure. This cyclic structure can be any of an aromatic ring or a non-aromatic ring, or a structure formed by the fusion of aromatic and non-aromatic rings. Examples of structures formed by the fusion of aromatic and non-aromatic rings include indimonic rings, fluorene rings, and similar structures. Regarding the "similar structures," examples include structures formed by bonding substituents to an indimonic or fluorene ring; structures in which the portion forming the non-aromatic ring in the indimonic or fluorene ring contains unsaturated bonds. Examples of substituents in the "structure formed by bonding substituents to an indimonic or fluorene ring" include, for example, halogen atoms, alkyl groups, alkoxy groups, aryl groups, aralkyl groups, silyl groups, acyl groups, acyloxy groups, carboxyl groups, sulfonyl groups, cyano groups, nitro groups, hydroxyl groups, mercapto groups, oxo groups, etc.

[0566] From the viewpoint of maximizing the desired effects of the present invention, (G) the liquid thermosetting resin preferably contains free radical polymerizable groups other than maleimide groups. Examples of free radical polymerizable groups other than maleimide groups include: vinyl, 1-propenyl, allyl (2-propenyl), isopropenyl, vinylphenyl, styrene, (meth)acryloyl, fumaroyl, etc.

[0567] In one embodiment, the (G) liquid thermosetting resin may have reactive groups other than free radical polymerizable groups. Examples of such reactive groups include amino, cyanate, anhydride, and mercapto groups. In a suitable embodiment, the (G) liquid thermosetting resin has an amino group.

[0568] From the viewpoint of maximizing the desired effects of the present invention, (G) the liquid thermosetting resin preferably contains one or more functional groups selected from vinyl, allyl, (meth)acryloyl and amino.

[0569] In a suitable embodiment, the (G) liquid thermosetting resin comprises a cyclic structure and a resin with one or more functional groups selected from vinyl, 1-propenyl, allyl, (meth)acryloyl, and amino. More preferably, the (G) liquid thermosetting resin comprises a cyclic structure and a resin with one or more functional groups selected from vinyl, allyl, (meth)acryloyl, and amino.

[0570] Examples of resins containing cyclic structures and vinyl groups include resins having one or more, preferably two or more, vinyl groups directly bonded to aromatic carbon atoms. Examples of such resins include divinylbenzene, 2,4-divinyltoluene, 2,6-divinylnaphthalene, and 1,4-divinylnaphthalene.

[0571] Resins containing cyclic structures and allyl groups preferably contain any cyclic structure selected from phenolic rings and carboxylic acid derivatives containing aromatic and / or non-aromatic rings.

[0572] Examples of resins containing phenolic rings and allyl groups include: cresol resins containing allyl groups, phenolic varnish-type phenolic resins containing allyl groups, and cresol phenolic varnish resins containing allyl groups. Commercially available examples of such resins include "MEH-8000H" and "MEH-8005" manufactured by Meiwa Kasei Corporation.

[0573] In resins containing carboxylic acid derivatives with aromatic and / or non-aromatic rings and allyl groups, examples of carboxylic acids containing aromatic and / or non-aromatic rings include isocyanuric acid, biphenyl phthalic acid, phthalic acid, and cyclohexanedicarboxylic acid. Specific examples of resins containing carboxylic acid derivatives with aromatic and / or non-aromatic rings and allyl groups include allyl isocyanurate, diallyl isocyanurate, triallyl isocyanurate, diallyl biphenyl phthalate, allyl biphenyl phthalate, o-diallyl phthalate, m-diallyl phthalate, p-diallyl phthalate, allyl cyclohexanedicarboxylate, and diallyl cyclohexanedicarboxylate. Commercially available examples of the aforementioned resins include: TAIC (traceryl isocyanurate) manufactured by Nippon Kasei Corporation; MDAC (allyl resin with cyclohexanedicarboxylic acid derivative) manufactured by Osaka Soda Corporation; DAD (diallyl biphenyl ester) manufactured by Nisshoku Techno Fine Chemical Co., Ltd.; and DAISO DAP Monomer (o-diallyl phthalate) manufactured by Osaka Soda Corporation.

[0574] In resins containing a cyclic structure and a (meth)acryloyl group, the cyclic structure is preferably a divalent cyclic group. The divalent cyclic group can be either a divalent aromatic group or a divalent aliphatic group containing a non-aromatic ring. 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.

[0575] From the viewpoint of maximizing the desired effects of the present invention, the divalent cyclic group is preferably a 3-membered ring or more, more preferably a 4-membered ring or more, even more preferably a 5-membered ring or more, preferably a 20-membered ring or less, more preferably a 15-membered ring or less, and even more preferably a 10-membered ring or less. Furthermore, the divalent cyclic group can be a monocyclic structure or a polycyclic structure.

[0576] Regarding the ring in the divalent cyclic group, in addition to carbon atoms, the ring skeleton can also be composed of heteroatoms. 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 heteroatoms.

[0577] Specific examples of divalent cyclic groups include the divalent groups (i) to (xi) described below. In the divalent groups (i) to (xi) described below, the wavy line indicates the bonding site. Among these, (x) or (xi) is preferred as the divalent cyclic group.

[0578] [Chemical Formula 36]

[0579]

[0580] The divalent cyclic group may have substituents. Examples of such substituents include: halogen atoms, alkyl groups, alkoxy groups, aryl groups, aralkyl groups, silyl groups, acyl groups, acyloxy groups, carboxyl groups, sulfonyl groups, cyano groups, nitro groups, hydroxyl groups, mercapto groups, oxo groups, etc., with alkyl groups being preferred.

[0581] In resins containing a cyclic structure and a (meth)acryloyl group, the (meth)acryloyl group can be directly bonded to the divalent cyclic group or bonded through a divalent linking group. Examples of divalent linking groups include: alkylene, alkenylene, arylene, heteroarylene, -C(=O)O-, -O-, -NHC(=O)-, -NC(=O)N-, -NHC(=O)O-, -C(=O)-, -S-, -SO-, -NH-, etc., and can be groups composed of multiple of these. Alkylene groups are preferred as divalent linking groups, with methylene and 1,1-dimethylethylene being particularly preferred.

[0582] Resins containing a cyclic structure and (meth)acryloyl groups are preferably resins represented by the following formula (G1).

[0583] [Chemical Formula 37]

[0584]

[0585] In formula (G1),

[0586] R G1 Each group represents (meth)acryloyl group independently;

[0587] R G2 Each can be used independently to represent a divalent linker;

[0588] Ring D 1 It represents a divalent cyclic group.

[0589] In equation (G1), R G1 Each group represents (meth)acryloyl group independently, preferably acryloyl group.

[0590] In equation (G1), R G2 Each of these represents a divalent linker independently. Regarding R... G2 The “divalent linking group” shown is the same as the divalent linking group that can bond to the (meth)acryloyl group mentioned above.

[0591] In equation (G1), ring D 1 This indicates a divalent cyclic group. Regarding ring G... 1 The "divalent cyclic group" shown is the same as the divalent cyclic group mentioned above. Cycle G 1 It may have substituents, and examples of such substituents include: halogen atoms, alkyl, alkoxy, aryl, aralkyl, silyl, acyl, acyloxy, carboxyl, sulfonyl, cyano, nitro, hydroxyl, mercapto, oxo, etc., with alkyl being preferred.

[0592] Commercially available resins containing cyclic structures and (meth)acryloyl groups include: "A-DOG" (reinforced by formula (G2-1) below) manufactured by Shin-Nakamura Chemical Industry Co., Ltd.; "DCP-A" (reinforced by formula (G2-2) below) manufactured by Kyoeisha Chemical Co., Ltd.; "NK ester DCP" (reinforced by formula (G2-3) below) manufactured by Shin-Nakamura Chemical Industry Co., Ltd.; and "KAYARAD R-684" and "KAYARAD R-604" manufactured by Nippon Kayaku Co., Ltd.

[0593] [Chemical Formula 38]

[0594]

[0595] Examples of resins containing cyclic structures and amino groups include alicyclic amines and aromatic amines. The number of amino groups in the resin is not particularly limited, but it is preferable that one molecule contains two or more amino groups. Furthermore, the resin can be any of primary, secondary, and tertiary amines. Specific examples of such resins include: 4,4'-methylenebis(2,6-dimethylaniline), diphenyl diamino sulfone, 4,4'-diaminodiphenylmethane, 4,4'-diaminodiphenyl sulfone, 3,3'-diaminodiphenyl sulfone, m-phenylenediamine, m-phenylenediamine, diethyltoluenediamine, 4,4'-diaminodiphenyl ether, 3,3'-dimethyl-4,4'-diaminobiphenyl, 2,2'-dimethyl-4,4'-diaminobiphenyl, 3,3'-dihydroxybenzidine, 2,2-bis(3-amino- 4-Hydroxyphenyl)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 products of the aforementioned resins include: "KAYAHARDA-A", "KAYAHARDA-B", and "KAYAHARDA-S" manufactured by Nippon Kayaku Co., Ltd.; and "WA" manufactured by Mitsubishi Chemical Co., Ltd.

[0596] In another suitable embodiment, (G) the liquid thermosetting resin comprises benzo[a] Azine resin. As described in the embodiments, benzo[a]benzyl ... Azine resins can be used that contain one or more, preferably two or more, benzo[a] groups within one molecule. Resins with aziridine rings. As benzo[a] Commercially available azine resins include "ALP-d" manufactured by Shikoku Chemical Industry Co., Ltd.

[0597] As described above, the (G) liquid thermosetting resin preferably contains a cyclic structure, but a liquid thermosetting resin without a cyclic structure may also be used as the (G) thermosetting resin. The liquid thermosetting resin without a cyclic structure preferably contains one or more functional groups selected from vinyl, 1-propenyl, allyl, (meth)acryloyl and amino, and more preferably contains (meth)acryloyl.

[0598] Commercially available resins containing (meth)acryloyl groups and without cyclic structures include Nippon Kayaku Co., Ltd.'s "NPGDA", "FM-400", "THE-330", "PET-30", and "DPHA".

[0599] (G) The active group equivalent of the liquid thermosetting resin 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, further preferably 500 g / eq. or less, and even more preferably 300 g / eq. or less. The active group equivalent of the liquid thermosetting resin (G) indicates the mass of (G) liquid thermosetting resin per 1 equivalent of active group. Furthermore, (v) the active group of the liquid thermosetting resin refers to a thermosetting functional group or structure, such as: free radical polymerizable groups like vinyl or (meth)acryloyl groups; reactive groups other than free radical polymerizable groups like amino or cyanate groups; benzo[…]. Reactive cyclic structures such as azin rings.

[0600] In the resin composition according to the first embodiment, from the viewpoint of better exerting the desired effect of the present invention, the content of component (G) in the resin composition is preferably 0.1% by mass or more, more preferably 0.5% by mass or more, further preferably 0.9% by mass or more, 1% by mass or more, 1.2% by mass or more, or 1.5% by mass or more, preferably 15% by mass or less, more preferably 10% by mass or less, 8% by mass or less, or 6% by mass or less, and further preferably 5% by mass or less, 4% by mass or less, 3% by mass or less, 2.5% by mass or less, or 2% by mass or less.

[0601] In the resin composition according to the first embodiment, from the viewpoint of better exerting the desired effect of the present invention, the content of component (G) in the resin composition is preferably 1% by mass or more, more preferably 2% by mass or more, further preferably 3% by mass or more, 4% by mass or more, 5% by mass or more, or 6% by mass or more, preferably 30% by mass or less, more preferably 25% by mass or less, further preferably 20% by mass or less, 15% by mass or less, 10% by mass or less, 8% by mass or less, or 7% by mass or less.

[0602] Relative to the non-volatile components in 100% by mass of the resin composition, when the content of component (G) is set as M... G When [mass %], the mass ratio of component (G) to component (A-1) (content of component (G) / content of component (A-1)) can be obtained from M G / M A1 This indicates that, from the viewpoint of producing cured products exhibiting excellent mechanical strength, the mass ratio M... G / M A1Preferably, it is 0.01 or more, more preferably 0.03 or more, and even more preferably 0.05 or more, 0.1 or more, 0.11 or more, 0.12 or more, or 0.13 or more. Furthermore, from the viewpoint of the heat resistance of the cured resin composition and the surface roughness after cleaning treatment, the mass ratio M... G / M A1 The upper limit is preferably 2 or less, more preferably 1 or less, and even more preferably 0.5 or less, 0.3 or less, 0.2 or less, or 0.15 or less. In the mass ratio M G / M A1 When the upper limit is below the aforementioned upper limit value, the resin composition produces a cured product with low surface roughness after roughening treatment, and is therefore more suitable.

[0603] Compared to the non-volatile components in 100% by mass of the resin composition, when the content of component (G) is M G When [mass %], the mass ratio of component (G) to component (B) (content of component (G) / content of component (B)) can be determined by M G / M B Indicated. From the viewpoint of the mechanical strength of the cured resin composition, the mass ratio M G / M B Preferably, it is 0.01 or more, more preferably 0.03 or more, and even more preferably 0.05 or more, 0.1 or more, 0.11 or more, 0.12 or more, or 1.13 or more. Furthermore, from the viewpoint of the heat resistance of the cured resin composition and the surface roughness after cleaning treatment, the mass ratio M... G / M B The upper limit is preferably 2 or less, more preferably 1 or less, and even more preferably 0.5 or less, 0.3 or less, 0.2 or less, or 0.15 or less.

[0604] Relative to the non-volatile components in 100% by mass of the resin composition, when the content of component (G) is set as M... G When [mass %], the mass ratio of component (G) to component (D) (content of component (G) / content of component (D)) can be obtained from M G / M D Indicated. From the viewpoint of the mechanical strength of the cured resin composition, the mass ratio M G / M D Preferably, it is 0.001 or more, more preferably 0.005 or more, and even more preferably 0.01 or more or 0.02 or more.

[0605] Furthermore, from the viewpoint of the heat resistance of the cured resin composition and the surface roughness after cleaning treatment, the mass ratio M G / M DThe upper limit is preferably 0.3 or less, more preferably 0.2 or less, and even more preferably 0.1 or less, 0.08 or less, or 0.05 or less.

[0606] Relative to the non-volatile components in 100% by mass of the resin composition, when the content of component (G) is set as M... G When [mass %], the mass ratio of component (C) to component (G) (content of component (C) / content of component (G)) can be determined by M. C / M G This indicates that, from the viewpoint of better achieving the desired effects of the invention, the mass ratio M... C / M G Preferably, it is 0.01 or more, more preferably 0.05 or more, and even more preferably 0.1 or more or 0.15 or more.

[0607] In addition, the mass ratio M C / M G The upper limit is preferably 1 or less, more preferably 0.8 or less, and even more preferably 0.6 or less, 0.4 or less, or 0.3 or less.

[0608] <(H) Other Additives>

[0609] The resin composition according to the first embodiment of the present invention may further include (H) other additives as optional components, in combination with the above-described components (A-1) to (G). The (H) other additives do not include substances equivalent to the above-described components (A-1) to (G).

[0610] Other additives (H) include, for example: solid thermosetting resins; organic fillers such as rubber granules; organometallic compounds such as organocopper compounds and organozinc compounds; colorants such as phthalocyanine blue, phthalocyanine green, iodine green, diazo yellow, crystal violet, titanium dioxide, and carbon black; polymerization inhibitors such as hydroquinone, catechol, pyrogallol, and phenothiazine; homogenizing agents such as organosilicon-based homogenizers and acrylic polymer-based homogenizers; thickeners such as Benton and montmorillonite; defoamers such as organosilicon-based defoamers, acrylic defoamers, fluorinated defoamers, and vinyl resin-based defoamers; and ultraviolet absorbers such as benzotriazole-based ultraviolet absorbers. Adhesives include: ureasilane and other adhesion enhancers; triazole-based, tetraazole-based, and triazine-based adhesion enhancers; hindered phenolic antioxidants; stilbene derivatives and other fluorescent whitening agents; fluorinated surfactants and organosilicon surfactants; nitrogen-based flame retardants (e.g., melamine sulfate), halogen-based flame retardants, and inorganic flame retardants (e.g., antimony trioxide); borate ester stabilizers, titanate ester stabilizers, aluminate ester stabilizers, zirconate ester stabilizers, isocyanate stabilizers, carboxylic acid stabilizers, and carboxylic anhydride stabilizers. (H) Other additives may be used individually or in combination of two or more. When the resin composition according to the first embodiment contains (H) other additives, the content of (H) components in the resin composition can be determined according to the required characteristics of the resin composition. Furthermore, the components (A-1) to (G) described above may have the following functions: organic filler, organometallic compound, colorant, polymerization inhibitor, homogenizer, thickener, defoamer, ultraviolet absorber, adhesion enhancer, adhesion promoter, antioxidant, fluorescent whitening agent, surfactant, flame retardant, dispersant, stabilizer, etc. In this case, the components are considered as each of the components (A-1) to (G) described above, rather than component (H). It should be noted that the resin composition involved in the first embodiment is not particularly limited, and generally, fluororesin as component (H) is not included. That is, substances containing fluororesin can be removed from the resin composition involved in the first embodiment.

[0611] <(I) Organic Solvents>

[0612] In the resin composition according to the first embodiment of the present invention, (I) an organic solvent may be further included as an optional volatile component in combination with the non-volatile components (A-1) to (H) 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; and solvents such as tetrahydropyran, tetrahydrofuran, and 1,4-di(2-dihydropyran). Ether solvents such as alkanes, diethyl ethers, diisopropyl ethers, dibutyl ethers, diphenyl ethers, and anisole; alcohol solvents such as methanol, ethanol, propanol, butanol, and ethylene glycol; 2-ethoxyethyl acetate, propylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, and carbitol acetate. Ether ester solvents such as acetate, γ-butyrolactone, and methyl methoxypropionate; 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. (I) Organic solvents may be used alone or in combination of two or more.

[0613] When the resin composition according to the first embodiment contains organic solvent (I), the content of component (I) in the resin composition may be, for example, 60% or less, 40% or less, 30% or less, 25% or less, or 20% or less, relative to 100% by mass of all components of the resin composition. Alternatively, the content of organic solvent (I) in the resin composition may be 0% by mass.

[0614] [The resin composition according to the second embodiment]

[0615] The resin composition according to the second embodiment of the present invention comprises: (A-2) a compound containing a second specific structural unit and a specific terminal group, (B) a maleimide resin, (C) a phosphorus-based flame retardant, and (D) an inorganic filler. By combining components (A-2), (B), (C), and (D) in the resin composition, a cured product with low dielectric loss tangent, excellent adhesion strength to the conductor layer, and excellent mechanical properties (specifically, puncture strength) can be obtained.

[0616] The resin composition according to the second embodiment may further contain optional components in combination with components (A-2), (B), (C), and (D). Examples of optional components include: (E) thermoplastic resin, (F) curing accelerator, (G) liquid thermosetting resin, (H) other additives, and (I) organic solvent. Hereinafter, each component contained in the resin composition according to the second embodiment will be described in detail.

[0617] <(A-2) Compounds containing a second specific structural unit and a specific terminal group>

[0618] The resin composition according to the second embodiment of the present invention comprises a compound containing a structural unit represented by the following formula (A2-1) and a terminal group represented by the following formula (y) (a compound containing a second specific structural unit and a specific terminal group) as component (A-2). Hereinafter, the structural unit represented by formula (A2-1) is sometimes referred to as "second specific structural unit" or "structural unit (2)". Component (A-2) may be used alone or in combination of two or more.

[0619] [Chemical Formula 39]

[0620]

[0621] In formula (A2-1),

[0622] R 21 Each can be represented independently as a divalent nitrogen-containing heteroaromatic group that may have substituents.

[0623] R 22 Each can be independently represented as a divalent aromatic hydrocarbon group that may have substituents.

[0624] R 23 This refers to a hydrocarbon group having 1 to 20 carbon atoms bonded to one or more groups represented by the following formula (a1).

[0625] X 2 Each can be independently represented as -O-, -S-, or -N(R) 24 )-,

[0626] R 24 A group that represents a hydrogen atom, a monovalent hydrocarbon group having 1 to 20 carbon atoms, a monovalent halohydrocarbon group having 1 to 20 carbon atoms, or a group in which the hydrocarbon group or a portion thereof is substituted by at least one of oxygen and sulfur atoms.

[0627] [Chemical Formula 40]

[0628] *-R 22 -X 2 -** (a1)

[0629] In equation (a1),

[0630] * indicates the site where a hydrocarbon group with 1 to 20 carbon atoms is bonded.

[0631] ** indicates the site where it bonds with other structural units contained in component (A-2).

[0632] R 22 and X 2 respectively with R in the above formula (A2-1) 22 and X 2same.

[0633] [Chemical Formula 41]

[0634]

[0635] In formula (y),

[0636] Y represents a monovalent organic group with 3 to 50 carbon atoms containing free radical polymerizable groups other than maleimide groups.

[0637] The wavy line indicates the bonding area.

[0638] In equation (A2-1), R 21 Each of these groups independently represents a divalent nitrogen-containing heteroaromatic group that may have substituents. R in formula (A2-1) 21 The example of "a divalent nitrogen-containing heteroaromatic group that may have substituents" is the same as R in formula (A1-1). 1 The same applies to "divalent nitrogen-containing heteroaromatic groups that may have substituents". Therefore, R 21 Preferably, it is a divalent group composed of a pyrimidine ring that may have substituents.

[0639] As R 21 The group represented may have substituents, such as R in formula (A1-1). 1 The substituents that the group represented may have are also the same.

[0640] From the perspective of the excellent polymerization reactivity in the synthesis of component (A-1), R 21 The substituents that the indicated group may have are preferably halogen atoms, hydrocarbon groups with 1 to 6 carbon atoms, halohydrocarbon groups with 1 to 6 carbon atoms, nitro, cyano, amino, or groups composed of amine salts, more preferably fluorine atoms, chlorine atoms, methyl, tert-butyl, phenyl, nitro, cyano, or primary amino, and even more preferably phenyl.

[0641] From the viewpoint of achieving the desired effect of the present invention, R 21 The indicated group preferably has no substituents or has phenyl as a substituent, more preferably has phenyl as a substituent.

[0642] For R 21 The two bonding sites in the represented group (with X) 2 The location of the bonding sites (equally bonded) is not particularly limited, but from the viewpoint of excellent polymerization reactivity in the synthesis of component (A-2), the meta position is preferred. In R 21 In the case where the divalent group is composed of a pyrimidine ring that may have substituents, for example, it is preferable to have a bonding site on the carbons at the 4 and 6 positions of the pyrimidine ring. Furthermore, in this case, as R... 21The bonding site of the substituent in the indicated group is preferably on the carbon at the 2-position of the pyrimidine ring.

[0643] In equations (A2-1) and (a1), R 22 Each can be independently represented as a divalent aromatic hydrocarbon group that may have substituents. Specific examples of divalent aromatic hydrocarbon groups include: arylene. Examples of arylene groups include: phenylene, naphthylene, anthracene, biphenylene (-C6H4-C6H4-), etc.

[0644] As R 22 The group represented may have substituents, such as R in formula (A1-1). 1 The substituents that the group represented may have are also the same.

[0645] R 22 Each of the represented groups is preferably represented by the structure shown in the following formula (A2-2).

[0646] [Chemical Formula 42]

[0647]

[0648] In formula (A2-2),

[0649] * indicates that R in the above formula (A2-1) 23 The bonding site, in formula (a1), represents the site where it is bonded to a hydrocarbon group having 1 to 20 carbon atoms;

[0650] *** represents X in equation (A2-1) or equation (a1). 2 The bonding site;

[0651] R 25 It refers to 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;

[0652] n A1 Represents integers from 0 to 2;

[0653] n A2 Represents integers from 0 to 4.

[0654] In equation (A2-2), R 25 It refers to 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.

[0655] As R 25 Alkyl groups having 1 to 10 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, etc.

[0656] As R25 Alkoxy groups with 1 to 10 carbon atoms include, for example: methoxy, ethoxy, n-propoxy, isopropoxy, butoxy, pentoxy, hexoxy, heptoxy, octoxy, etc.

[0657] As R 25 Cycloalkyl groups having 3 to 10 carbon atoms include, for example, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

[0658] In equation (A2-2), n A1 It represents an integer from 0 to 2, preferably 0 or 1.

[0659] In equation (A2-2), n A2 It represents an integer from 0 to 4, preferably an integer from 1 to 3.

[0660] The structure represented by formula (A2-2) is preferably the following formula (A2-3-1) or the following formula (A2-3-2).

[0661] [Chemical Formula 43]

[0662]

[0663] In equations (A2-3-1) and (A2-3-2),

[0664] R 26 Each can be independently represented as 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;

[0665] n A3 Represents integers from 0 to 3;

[0666] n A4 Represents integers from 0 to 2;

[0667] *、***、R 25 and n A1 respectively with *, ***, and R in the above formula (A2-2) 25 and n A1 same.

[0668] In equations (A2-3-1) and (A2-3-2), R 26 Each of the following can be independently represented: 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. R 26 The examples of "alkyl groups having 1 to 10 carbon atoms, alkoxy groups having 1 to 10 carbon atoms, or cycloalkyl groups having 3 to 10 carbon atoms" are the same as R in formula (A2-2). 25 The same applies to "alkyl groups having 1 to 10 carbon atoms, alkoxy groups having 1 to 10 carbon atoms, or cycloalkyl groups having 3 to 10 carbon atoms".

[0669] In equation (A2-3-1), n A3 It represents an integer from 0 to 3, preferably an integer from 0 to 2.

[0670] In equation (A2-3-2), n A4 It represents an integer from 0 to 2, preferably 0 or 1.

[0671] In equation (A2-1), R 23 This refers to a hydrocarbon group with 1 to 20 carbon atoms bonded to one or more groups represented by formula (a1). For R 23 The structure of the "hydrocarbon group with 1 to 20 carbon atoms" is not particularly limited; it can be any structure composed of aliphatic groups, aromatic groups, or a combination of aliphatic and aromatic groups. Furthermore, the aliphatic group can be a chain hydrocarbon group, a cyclic hydrocarbon group (i.e., an alicyclic hydrocarbon group), or a combination thereof. Moreover, the chain hydrocarbon group can be either straight-chain or branched.

[0672] R 23 In the groups represented, when the portion of the group represented by formula (a1) is removed and set to A, in the structural unit represented by formula (A2-1), -R 22 -R 23 -R 22 - The partial structure can be represented by the following equation (A2-4). That is, the structural unit represented by equation (A2-1) has a branched structure.

[0673] [Chemical Formula 44]

[0674]

[0675] In formula (A2-4),

[0676] A represents R in equation (A2-1) 23 Remove the portion of the group represented by formula (a1) from the group represented;

[0677] n A5 Represents integers greater than or equal to 1;

[0678] Regarding the other symbols, see above.

[0679] In equation (A2-4), A represents R from equation (A2-1). 23 The portion of the group represented by formula (a1) is removed from the group represented. The branched structure represented by formula (A2-4) is preferably formed by the tertiary or quaternary carbon of the group represented by A.

[0680] In equations (A2-1) and (a1), X 2Each can be independently represented as -O-, -S-, or -N(R) 24 )-. Additionally, X 2 The represented group may have R 24 This refers to a group that represents a hydrogen atom, a monovalent hydrocarbon group having 1 to 20 carbon atoms, a monovalent halohydrocarbon group having 1 to 20 carbon atoms, or a group in which the hydrocarbon group or a portion thereof is substituted by at least one atom selected from oxygen and sulfur atoms. It should be noted that when there are two or more X atoms... 2 They are -N(R) 24 In the case of )-, X 2 The R represented by the group 24 They can be the same or different.

[0681] As R 24 The monovalent hydrocarbon groups representing 1 to 20 carbon atoms, and R as in formula (A1-1) 1 The group represented may have substituents of "monovalent hydrocarbon groups with 1 to 20 carbon atoms".

[0682] As R 24 The monovalent haloalkyl group representing 1 to 20 carbon atoms, and R as in formula (A1-1) 1 The group represented may have substituents of "monovalent haloalkyl groups with 1 to 20 carbon atoms".

[0683] As R 24 The phrase "the hydrocarbon group or part of the halohydrocarbon group is substituted by at least one group selected from oxygen and sulfur atoms" is related to R in formula (A1-1). 1 The group represented may have substituents, meaning that "the hydrocarbon group or part of the halohydrocarbon group is selected from at least one substituent of oxygen and sulfur atoms".

[0684] Among them, from the perspective of the excellent polymerization reactivity in the synthesis of component (A-2), R 24 Preferably, it contains hydrogen atoms or hydrocarbon groups with 1 to 10 carbon atoms.

[0685] In formula (a1), ** represents the site where it bonds to other structural units contained in component (A-2). Here, other structural units can be other structural units represented by formula (A2-1) (hereinafter also referred to as "structural unit (2')"), or structural unit (1) described later (the structural unit represented by formula (A1-1), other structural units (structural units other than structural units (2) and (1)), or terminal groups represented by formula (y). It should be noted that when the ** in structural unit (2) bonds to structural unit (2'), the ** in structural unit (2) bonds to the R in structural unit (2'). 21The indicated group is bonded, but not to X in the structural unit (2'). 2 Bonding.

[0686] In addition to structural unit (2), component (A-2) preferably further contains structural unit (1) contained in component (A-1). That is, in a suitable embodiment, component (A-2) further contains structural unit represented by the following formula (A1-1).

[0687] [Chemical Formula 45]

[0688]

[0689] In formula (A1-1),

[0690] R 1 Each can be independently represented as a divalent nitrogen-containing heteroaromatic group that may have substituents;

[0691] R 2 Each can be used independently to represent a divalent organic group;

[0692] X 1 Each can be independently represented as -O-, -S-, or -N(R) 3 )-;

[0693] R 3 A group that represents a hydrogen atom, a monovalent hydrocarbon group having 1 to 20 carbon atoms, a monovalent halohydrocarbon group having 1 to 20 carbon atoms, or a group in which the hydrocarbon group or a portion thereof is substituted by at least one of oxygen and sulfur atoms.

[0694] Regarding the structural unit (structural unit (1)) represented by formula (A1-1), it is as explained in the items of the above (A-1) components.

[0695] In formula (y), Y represents a monovalent organic group with 3 to 50 carbon atoms containing a free radical polymerizable group other than a maleimide group. The group represented by Y in component (A-2) is the same as the group represented by Y in component (A-1). Therefore, in component (A-2), the group represented by Y preferably includes: a monovalent aromatic group containing a free radical polymerizable group, more preferably a monovalent group selected from vinylphenyl, allylphenyl, isopropenylphenyl and vinylbenzyl, and even more preferably vinylbenzyl.

[0696] When the group represented by Y is bonded to structural unit (2) in component (A-2), the group represented by Y is bonded to X in structural unit (2). 2 The indicated group is bonded, but not to R in structural unit (2). 21Bonding. Furthermore, in the case where the group represented by Y is bonded, for example, to structural unit (1) in component (A-2), the group represented by Y is bonded to X in structural unit (1). 1 The groups represented are bonded, but not to R in structural unit (1). 1 Bonding.

[0697] (A-2) Components can be synthesized using known methods. (A-2) Components can be synthesized, for example, as follows: [The following text appears to be a separate, unrelated sentence: "Containing R..."] 21 The structure of the represented group is a raw material compound containing R. 22 -R 23 -R 22 The starting material compound containing the group represented by Y, and the starting material compound containing the group represented by Y (and the starting material compound containing the required structural unit (1) and / or the compound deriving other structural units (structural units other than structural units (2) and (1))) are heated in an organic solvent together with an alkali metal or alkali metal compound (and the required polymerization inhibitor). Regarding the starting material compound containing the group represented by Y (the starting material compound containing the required structural unit (1) and the compound deriving other structural units), when the starting material containing R... 21 The structure of the represented group in the raw material compound and the compound containing R 22 -R 23 -R 22 After the raw material compound representing the structure of the group is reacted, it is heated and mixed to allow it to react.

[0698] In the synthesis of component (A-2), as a component containing R 21 The structure of the represented group is a starting material compound, for example, one containing R used in the synthesis of component (A-1). 1 The raw material compounds with the represented groups have the same structure. These compounds can be used alone or in combination of two or more.

[0699] In the synthesis of component (A-2), as a component containing R 22 -R 23 -R 22 The starting material compounds with the represented group structure can be exemplified by, for example, compounds represented by the following formula (A2-5). Compounds represented by formula (A2-5) can be used alone or in combination of two or more.

[0700] [Chemical Formula 46]

[0701]

[0702] In formula (A2-5),

[0703] A' represents nA6 Hydrocarbon groups with 1 to 20 carbon atoms;

[0704] R 27 Each can be independently represented as 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;

[0705] n A6 Represents integers from 2 to 4;

[0706] n A7 Each can independently represent an integer from 1 to 5;

[0707] n A8 Each of the integers from 0 to 4 can be represented independently, where 1 ≤ n. A7 +n A8 ≤5.

[0708] The compound represented by formula (A2-5) is preferably the compound represented by formula (A2-6-1) or formula (A2-6-2) below.

[0709] [Chemical Formula 47]

[0710]

[0711] In equations (A2-6-1) and (A2-6-2), A' and R 27 and n A6 respectively with A' and R in the above formula (A2-5) 27 and n A6 same.

[0712] As a specific example of the compounds represented by formula (A2-5), the following compounds can be cited:

[0713] [Chemical Formula 48]

[0714]

[0715] In the synthesis of component (A-2), the starting compound containing the group represented by Y is, for example, the same starting compound containing the group represented by Y used in the synthesis of component (A-1). These compounds may be used individually or in combination of two or more.

[0716] In the case where component (A-2) contains structural unit (1), R is included as structural unit (1). 2 The starting material compounds with the indicated groups are as described in the synthesis of component (A-1). One compound may be used alone, or two or more may be used in combination.

[0717] When component (A-2) contains other structural units (structural units other than structural units (2) and (1), compounds derived from these other structural units may include, for example: diphenyl carbonate, thiodiphenyl carbonate, selenodiphenyl carbonate, phosgene, sulfophosgene, selenophosgene, etc., which are compounds that derive structural units containing carbonate bonds, thiocarbonate bonds, or selenocarbonate bonds; dihydroxy compounds such as benzyl glycol and cyclohexanediethanol; phosphine oxide compounds such as bis(fluorophenyl)phenylphosphine oxide, bis(fluorophenyl)naphthylphosphine oxide, bis(fluorophenyl)anthraylphosphine oxide; and dihalides of dicarboxylic acids such as phthaloyl dichloro, isophthaloyl dichloro, and terephthaloyl dichloro. These compounds may be used individually or in combination of two or more.

[0718] In the synthesis of component (A-2), the alkali metal and alkali metal compound are the same as those used in the synthesis of component (A-1). Therefore, the alkali metal and alkali metal compound used in the synthesis of component (A-2) is preferably an alkali metal carbonate, more preferably potassium carbonate.

[0719] In the synthesis of component (A-2), the organic solvent used is, for example, the same organic solvent used in the synthesis of component (A-1). Therefore, the organic solvent used to synthesize component (A-2) is preferably 2-heptanone, cyclohexanone, N-methyl-2-pyrrolidone, toluene and / or xylene, more preferably N-methyl-2-pyrrolidone, 2-heptanone and / or cyclohexanone.

[0720] In the synthesis of component (A-2), from the viewpoint of controlling the polymerization reaction and obtaining component (A-2) with the desired molecular weight, a polymerization inhibitor can be used. The polymerization inhibitor used is the same as that used in the synthesis of component (A-1).

[0721] In the synthesis of component (A-2), R is included. 21 The structure of the represented group in the raw material compound and the compound containing R 22 -R 23 -R 22 The reaction temperature for reacting the starting compound with the indicated group structure (and the starting compound of the required structural unit (1) and / or compounds deriving 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. Furthermore, the reaction time is preferably 1 hour or higher, more preferably 2 hours or higher, further preferably 3 hours or higher, preferably 100 hours or lower, more preferably 50 hours or lower, and even more preferably 24 hours or lower.

[0722] In the synthesis of component (A-2), when R is included... 21 The structure of the represented group in the raw material compound and the compound containing R22 -R 23 -R 22 After reacting the starting compound with the structure represented by the group Y, and then reacting the starting compound with the structure represented by the group Y (and the starting compound with the required structural unit (1) and / or the compound deriving other structural units), 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. Furthermore, the reaction time is preferably 1 hour or higher, more preferably 2 hours or higher, further preferably 3 hours or higher, preferably 48 hours or lower, more preferably 24 hours or lower, and even more preferably 10 hours or lower.

[0723] The weight-average molecular weight (Mw) of component (A-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 (A-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 (A-2) can be determined as a polystyrene equivalent using gel permeation chromatography (GPC).

[0724] When all structural units contained in component (A-2) are set to 100 mol%, the content of structural unit (2) in component (A-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.

[0725] When component (A-2) contains structural unit (1), and when all structural units contained in component (A-2) are set to 100 mol%, the content of structural unit (1) in component (A-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.

[0726] In the resin composition according to the second embodiment, from the viewpoint of better exerting the desired effect of the present invention, the content of component (A-2) in the resin composition is preferably 1% by mass or more, more preferably 3% by mass or more, and even more preferably 5% by mass or more, 6% by mass or more, 7% by mass or more, 8% by mass or more, 10% by mass or more, 11% by mass or more, 12% by mass or more, or 13% by mass or more, relative to the non-volatile components in 100% by mass of the resin composition. In one embodiment, the lower limit of the content of component (A-2) in the resin composition relative to the non-volatile components in 100% by mass of the resin composition may be 14% by mass or more, 15% by mass or more, 16% by mass or more, 18% by mass or more, 20% by mass or more, or 21% by mass or more.

[0727] From the viewpoint of maximizing the desired effects of the present invention, the upper limit of the content of component (A-2) in the resin composition relative to the non-volatile components in 100% by mass of the resin composition is preferably 35% by mass or less, more preferably 30% by mass or less, and even more preferably 25% by mass or less, 23% by mass or less, 21% by mass or less, 20% by mass or less, or 18% by mass or less. In one embodiment, the upper limit of the content of component (A-2) in the resin composition relative to the non-volatile components in 100% by mass of the resin composition may be 16% by mass or less, 15% by mass or less, 14% by mass or less, 13% by mass or less, 12% by mass or less, 11% by mass or less, 10% by mass or less, 8% by mass or less, 7% by mass or less, or 6% by mass or less.

[0728] In the resin composition according to the second embodiment, from the viewpoint of better exerting the desired effect of the present invention, the content of component (A-2) in the resin composition is preferably 10% by mass or more, more preferably 15% by mass or more, and even more preferably 20% by mass or more, 25% by mass or more, 30% by mass or more, 35% by mass or more, 40% by mass or more, or 42% by mass or more, relative to the resin component in 100% by mass of the resin composition. In one embodiment, the content of component (A-2) in the resin composition may be 45% by mass or more, 50% by mass or more, 55% by mass or more, 60% by mass or more, 68% by mass or more, or 70% by mass or more, relative to the resin component in 100% by mass of the resin composition.

[0729] From the viewpoint of maximizing the desired effects of the present invention, the upper limit of the content of component (A-2) in the resin composition relative to the resin component in 100% by mass of the resin composition is preferably 85% by mass or less, more preferably 75% by mass or less, and even more preferably 70% by mass or less, or 68% by mass or less, 60% by mass or less, 55% by mass or less, or 50% by mass or less. In one embodiment, the upper limit of the content of component (A-2) in the resin composition relative to the resin component in 100% by mass of the resin composition may be 45% by mass or less, 42% by mass or less, 40% by mass or less, 35% by mass or less, 30% by mass or less, 25% by mass or less, or 20% by mass or less.

[0730] In addition to components (A-2), the resin composition according to the second embodiment of the present invention also includes (B) maleimide resin, (C) phosphorus-based flame retardant, and (D) inorganic filler. The resin composition according to the second embodiment of the present invention may also include (E) thermoplastic resin, (F) curing accelerator, (G) liquid thermosetting resin, (H) other additives, and (I) organic solvent. Components (B) to (I) in the resin composition according to the second embodiment may be the same as those in the resin composition according to the first embodiment. The content range of components (B) to (I) in the second embodiment may be the same as the content range described in the resin composition according to the first embodiment. Components (B) to (I) may be used individually or in combination of two or more.

[0731] The range of the mass ratio of component (A-2) to other components in the resin composition according to the second embodiment of the present invention is the same as the range of the mass ratio of component (A-1) to other components in the resin composition according to the first embodiment of the present invention.

[0732] In one example, regarding the range of the mass ratio of component (A-2) to component (B) in the resin composition according to the second embodiment of the present invention (content of component (A-2) / content of component (B)), it can be applied by replacing "component (A-1)" with "component (A-2)" within the range of the mass ratio of component (A-1) to component (B) in the resin composition according to the first embodiment of the present invention.

[0733] Specifically, relative to the non-volatile components in 100% by mass of the resin composition, when the content of component (A-2) is set as M... A2 [mass %], set the content of component (B) as M. BWhen [mass %], the mass ratio of component (A-2) to component (B) (content of component (A-2) / content of component (B)) can be determined by M. A2 / M B This indicates that, from the viewpoint of a cured product that can provide exceptionally strong adhesion to the conductor layer, as well as excellent mechanical strength and heat resistance, the quality ratio of M... A2 / M B Preferably, it is 0.1 or more, more preferably 0.2 or more, and even more preferably 0.3 or more, 0.5 or more, 0.8 or more, or 1 or more. In the mass ratio M... A2 / M B When the lower limit is above the aforementioned lower limit value, a resin composition that produces a cured product with low surface roughness after roughening treatment can be obtained, and is therefore more suitable. From the viewpoint that it can produce a cured product with particularly excellent adhesion strength to the conductor layer and also a cured product with excellent mechanical strength, the quality ratio M A2 / M B The upper limit is preferably 5 or less, more preferably 4 or less, and even more preferably 3 or less, 2 or less, or 1.5 or less.

[0734] Regarding the range of the mass ratio (content of (C) component / content of (A-2) component) of the resin composition according to the second embodiment of the present invention, it can be applied by replacing "(A-1) component" with "(A-2) component" within the range of the mass ratio (content of (C) component / content of (A-1) component) of the resin composition according to the first embodiment of the present invention.

[0735] Specifically, relative to the non-volatile components in 100% by mass of the resin composition, when the content of component (A-2) is set as M... A2 [mass %], set the content of component (C) as M. C When [mass %], the mass ratio of component (C) to component (A-2) (content of component (C) / content of component (A-2)) can be determined by M C / M A2 This indicates that, from the viewpoint of better achieving the desired effects of the invention, the mass ratio M... C / M A2 Preferably, it is 0.01 or higher, more preferably 0.02 or higher, and even more preferably 0.025 or higher. Mass ratio M C / M A2 The upper limit is preferably 0.1 or less, more preferably 0.08 or less, and even more preferably 0.06 or less, 0.04 or less, or 0.03 or less.

[0736] Regarding the range of the mass ratio (content of (G) component / content of (A-2) component) of the resin composition according to the second embodiment of the present invention, it can be applied by replacing "(A-1) component" with "(A-2) component" within the range of the mass ratio (content of (G) component / content of (A-1) component) of the resin composition according to the first embodiment of the present invention.

[0737] Specifically, relative to the non-volatile components in 100% by mass of the resin composition, when the content of component (G) is set as M... G When [mass %], the mass ratio of component (G) to component (A-2) (content of component (G) / content of component (A-2)) can be determined by M G / M A2 This indicates that, from the viewpoint of producing cured products exhibiting excellent mechanical strength, the mass ratio M... G / M A2 Preferably, it is 0.01 or more, more preferably 0.03 or more, and even more preferably 0.05 or more, 0.1 or more, 0.11 or more, 0.12 or more, or 0.13 or more. Furthermore, from the viewpoint of the heat resistance of the cured resin composition and the surface roughness after cleaning treatment, the mass ratio M... G / M A2 The upper limit is preferably 2 or less, more preferably 1 or less, and even more preferably 0.5 or less, 0.3 or less, 0.2 or less, or 0.15 or less. In the mass ratio M G / M A1 When the upper limit is below the aforementioned upper limit value, the resin composition produces a cured product with low surface roughness after roughening treatment, and is therefore more suitable.

[0738] It should be noted that (B) maleimide resin does not contain substances equivalent to components (A-2) above. Unless otherwise stated, (E) thermoplastic resin does not contain substances equivalent to components (A-2) to (D) above. Unless otherwise stated, (F) curing accelerator does not contain substances equivalent to components (A-2) to (E) above.

[0739] Furthermore, in both the first and second embodiments, the resin composition may or may not contain epoxy resin. From the viewpoint of maximizing the desired effect of the present invention, the content of epoxy resin in the resin composition is preferably 3% by mass or less, more preferably 2% by mass or less, and even more preferably 1% by mass or less, 0.5% by mass or less, 0.3% by mass or less, 0.1% by mass or less, or 0.05% by mass or less, with the lower limit being 0% by mass.

[0740] Furthermore, from the viewpoint of maximizing the desired effect of the present invention, whether in the first embodiment or the second embodiment, when the total content of component (B) and epoxy resin is set to 100% by mass, the content of phosphorus-based flame retardant (C) in the resin composition is preferably 1% by mass or more, more preferably 2% by mass or more, even more preferably 2.5% by mass or more, and preferably 10% by mass or less, more preferably 8% by mass or less, even more preferably 6% by mass or less, 4% by mass or less, or 3% by mass or less.

[0741] Furthermore, from the viewpoint of maximizing the desired effects of the present invention, in both the first and second embodiments, when the total content of components (A-1), (A-2), (B), (E), (G), and epoxy resin is set to 100% by mass, the content of phosphorus-based flame retardant (C) in the resin composition is preferably 0.03% by mass or more, more preferably 0.15% by mass or more, further preferably 0.3% by mass or more, 0.5% by mass or more, 0.7% by mass or more, or 0.9% by mass or more, preferably 10% by mass or less, more preferably 5% by mass or less, and even more preferably less than 5% by mass, 4% by mass or less, 3.5% by mass or less, 3% by mass or less, 2.5% by mass or less, 2% by mass or less, or 1.5% by mass or less.

[0742] [Method for manufacturing the resin composition]

[0743] The resin composition of the present invention can be manufactured, for example, by mixing components that may be contained in the resin composition. Therefore, the resin composition can be manufactured by a manufacturing method comprising the steps of mixing (A) a compound containing specific structural units and specific terminal groups, (B) a maleimide resin, (C) a phosphorus-based flame retardant, and (D) an inorganic filler. This manufacturing method may also include the step of mixing optional components such as components (E) to (I). Components (A) to (I) may be mixed simultaneously or sequentially. Additionally, as needed, the manufacturing method may include mixing or stirring the resin composition using a mixing apparatus such as a three-roll mill, ball mill, bead mill, sand mill, or a stirring apparatus such as a super mixer, planetary mixer, or high-speed rotary mixer.

[0744] [Properties of the resin composition and its cured product]

[0745] The resin composition of the present invention comprises: (A) a compound containing specific structural units and specific terminal groups, (B) a maleimide resin, (C) a phosphorus-based flame retardant, and (D) an inorganic filler, and, as needed, (E) a thermoplastic resin, (F) a curing accelerator, (G) a liquid thermosetting resin, (H) other additives, and (I) an organic solvent. Therefore, it can produce a cured product with low dielectric loss tangent, excellent adhesion strength to the conductor layer, and excellent mechanical properties (specifically, high puncture strength). Furthermore, an insulating layer can be formed by this cured product. Generally, since heat is applied during the curing of the resin composition, volatile components such as (I) the organic solvent contained in the resin composition can evaporate due to the heat during curing. Therefore, the cured product obtained by curing the resin composition may contain non-volatile components such as (A) to (H) or their reaction products.

[0746] The cured resin composition of the present invention can have excellent dielectric properties, specifically, it can have a low dielectric loss tangent Df. In one example, the dielectric loss tangent Df of the cured product is preferably 0.0032 or less, more preferably 0.0030 or less, and even more preferably 0.0028 or less. There is no particular limitation on the lower limit of the dielectric loss tangent Df, for example, it can be 0.0010 or more.

[0747] The resin composition of the present invention is characterized by producing a cured product with good adhesion strength (electroplated peel strength) to the electroplated 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 electroplated conductor layer can be obtained. The peel strength to the electroplated 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, 0.45 kgf / cm or more, or 0.5 kgf / cm or more. A higher upper limit for the peel strength is preferable; for example, it can be 2 kgf / cm or less. The peel strength can be measured according to the method described in the section "Test Example 2: Determination of Arithmetic Mean Roughness and Peel Strength to Electroplated Conductor Layer" described later.

[0748] From the viewpoint of improving the adhesion between the resin composition and the electroplated conductor layer, the arithmetic mean roughness (roughness, Ra) of the cured resin composition of the present invention is preferably 30 nm or more, more preferably 35 nm or more, and even more preferably 40 nm or more. The upper limit is preferably 500 nm or less, more preferably 400 nm or less, and even more preferably 300 nm or less. The arithmetic mean roughness (roughness, Ra) can be measured according to the method described in the section "Experimental Example 2: Determination of Arithmetic Mean Roughness and Peel Strength to Electroplated Conductor Layer" described later.

[0749] The resin composition of the present invention can produce cured products exhibiting excellent mechanical properties. Therefore, the cured products of the resin composition of the present invention can have high rigidity and toughness. For example, for an evaluation cured product obtained by curing the resin composition of the present invention at 190°C for 90 minutes, when punctured with a needle of 1 mm diameter at a speed of 50 mm / min, the strength at break (puncture strength) of the evaluation cured product punctured by the needle is preferably 0.9 N or more, more preferably 1 N or more, and even more preferably 1.2 N or more. The higher the upper limit of the puncture strength, the better; for example, it can be 10 N or less. The puncture strength can be determined according to the method described in the <Test Example 3: Stab Test> section below.

[0750] The resin composition of the present invention can produce cured products with high glass transition temperatures. Therefore, the resin composition of the present invention can produce cured products with excellent heat resistance. For example, as described in the section "Experimental Example 4: Determination of Glass Transition Temperature Tg" below, when the measurement is performed using a thermomechanical analysis apparatus, the glass transition temperature (Tg) of the cured resin composition is preferably 130°C or higher, more preferably 140°C or higher, and even more preferably 150°C or higher. There is no particular limitation on the upper limit of the glass transition temperature (Tg) of the cured resin composition; it can be set to 400°C or lower, 300°C or lower, etc.

[0751] The cured resin compositions of the present invention generally exhibit excellent crack resistance. For example, when an insulating layer is formed from the cured material using the method described in Example 5. Evaluation of Crack Resistance (described later), and its crack resistance is evaluated, the number of cracks can be reduced to 10 or less.

[0752] The cured product obtained by curing the resin composition layer containing the resin composition of the present invention exhibits excellent flame retardant properties. Therefore, the cured product provides an insulating layer with excellent flame retardant properties. Regarding flame retardancy, a flame retardancy test according to the UL94 standard is performed, preferably "V-1", more preferably "V-0" or better. The evaluation of flame retardancy can be determined according to the method described in the "Test Example 6: Evaluation of Flame Retardancy" section of the examples described later.

[0753] <Uses of Resin Compositions>

[0754] The resin composition described in this embodiment can be used for forming insulating layers, and is particularly preferred for forming insulating layers on circuit boards. Additionally, the resin composition can be used to manufacture resin sheets. Typically, insulating layers are formed using these resin sheets. Furthermore, the resin composition can be used for other applications, such as solder resists, underfill materials, chip bonding materials, via-filling resins, sealing resins, and component embedding resins.

[0755] <Resin Sheets>

[0756] One embodiment of the present invention relates to a resin sheet comprising: a support and a resin composition layer formed on the support. The resin composition layer comprises the above-described resin composition, preferably comprising only the above-described resin composition.

[0757] From the viewpoint of thinness, the thickness of the resin composition layer in 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 can be, for example, 1 μm or more, 3 μm or more, 5 μm or more, etc.

[0758] Examples of supports include: plastic film, metal foil, and release paper, with plastic film and metal foil being preferred.

[0759] When using a plastic film as a support, examples of plastic materials include: polyesters such as polyethylene terephthalate (PET) and polyethylene naphthalate (PEN); acrylics such as polycarbonate (PC); methyl methacrylate (PMMA); cyclic polyolefins; triacetyl cellulose (TAC); polyether sulfide (PES); polyether ketone; and polyimide. Among these, polyethylene terephthalate and polyethylene naphthalate are preferred, with inexpensive polyethylene terephthalate being particularly preferred.

[0760] When using metal foil as a support, examples of metal foils include copper foil and aluminum foil, with copper foil being preferred. As copper foil, foil containing a single metal such as copper can be used, or foil containing an alloy of copper with other metals (e.g., tin, chromium, silver, magnesium, nickel, zirconium, silicon, titanium, etc.) can be used.

[0761] For the support, surface treatments such as matte treatment, corona treatment, and antistatic treatment can also be applied to the surface that bonds with the resin composition layer.

[0762] As a support, a support with a release layer can be used on the surface that bonds to the resin composition layer. Examples of release agents used in the release layer of the support with a release layer include, for example, one or more release agents selected from alkyd release agents, polyolefin release agents, urethane release agents, and silicone release agents. Commercially available products can be used as supports with release layers, such as PET films having a release layer primarily composed of a silicone release agent or an alkyd resin release agent, such as LINTEC's "PET501010", "SK-1", "AL-5", and "AL-7"; Toray's "Lumirror T60"; Teijin's "Purex"; and UNITIKA's "Unipeel".

[0763] There is no particular limitation on the thickness of the support, but it 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.

[0764] When using a metal foil as a support, a metal foil with a peelable support substrate can be used, obtained by bonding a thin metal foil to a peelable support substrate. In one embodiment, the metal foil with a support substrate includes: a support substrate, a release layer disposed on the support substrate, and a metal foil disposed on the release layer. When using a metal foil with a support substrate as a support, a resin composition layer is disposed on the metal foil.

[0765] In metal foils with a supporting substrate, the material of the supporting substrate is not particularly limited; examples include copper foil, aluminum foil, stainless steel foil, titanium foil, and copper alloy foil. When using copper foil as the supporting substrate, it can be electrolytic copper foil or rolled copper foil. Furthermore, the release layer is not particularly limited as long as it can peel the metal foil off the supporting substrate; examples include alloy layers selected from elements such as Cr, Ni, Co, Fe, Mo, Ti, W, and P; and organic films.

[0766] In metal foils with a supporting substrate, the preferred material for the metal foil is, for example, copper foil or copper alloy foil.

[0767] In metal foils with a supporting substrate, the thickness of the supporting substrate is not particularly limited, but is preferably in the range of 10 μm to 150 μm, and more preferably in the range of 10 μm to 100 μm. Alternatively, the thickness of the metal foil can be set, for example, in the range of 0.1 μm to 10 μm.

[0768] Depending on the requirements, the resin sheet may also have optional components. For example, the resin sheet may also have a protective film that protects the resin composition layer. The protective film is usually provided on the side of the resin composition layer that is not in contact with the support (i.e., the side opposite to the support). There is no particular limitation on the thickness of the protective film, for example, it is 1 μm to 40 μm. With the protective film, dust can be prevented from adhering to the surface of the resin composition layer or causing damage to the surface of the resin composition layer.

[0769] Resin sheets can be manufactured, for example, by a method comprising forming a resin composition layer on a support. As a specific example, a resin varnish, which is a resin composition, is applied to a support and further dried to form a resin composition layer, thereby producing a resin sheet.

[0770] The resin composition can be coated using a coating apparatus such as a die coater. Drying can be performed, for example, by heating or blowing hot air. There are no particular limitations on the drying conditions; drying is generally carried out when the solvent content in the resin composition layer is typically 10% by mass or less, preferably 5% by mass or less. Although this varies depending on the boiling point of the solvent, for example, when using a resin composition containing 30% to 60% by mass of solvent, a resin composition layer can be formed by drying at 50°C to 150°C for 3 to 10 minutes.

[0771] The manufactured resin sheets can be wound into rolls for storage. When the resin sheet has a protective film, it can usually be used by peeling off the protective film.

[0772] <Circuit Board>

[0773] One embodiment of the present invention relates to a circuit board comprising a cured form of the aforementioned resin composition. Typically, the circuit board includes a cured layer comprising a cured form of the resin composition. The cured layer may contain only a cured form of the resin composition. The cured layer may be used, for example, as an insulating layer such as an interlayer insulating layer. There is no particular limitation on the thickness of the cured layer; for example, it may be within the same range as the thickness of the resin composition layer on the resin sheet. Furthermore, the cured layer typically has the same properties as the cured form of the aforementioned resin composition.

[0774] Preferably, the circuit board includes an inner substrate on which the cured layer, serving as an insulating layer, is provided. Additionally, the circuit board may include a conductor layer. For example, a conductor layer may be provided on the insulating layer. Hereinafter, examples of preferred methods for manufacturing the circuit board will be described.

[0775] The preferred embodiment involves a method for manufacturing a circuit board, including:

[0776] Step (I) involves forming a resin composition layer on an inner substrate; and

[0777] Step (II) cures the resin composition layer.

[0778] An "inner layer substrate" is a component that serves as the base material for a circuit board. Examples include glass epoxy boards, metal substrates, polyester substrates, polyimide substrates, BT resin substrates, and thermosetting polyphenylene ether substrates. Furthermore, the inner layer substrate may have conductive layers on one or both sides. The conductive layers of the inner layer substrate may also be patterned. Circuit wiring can be formed based on the patterned conductive layers. Sometimes, an inner layer substrate with conductive layers formed on one or both sides of the substrate is referred to as an "inner layer circuit board." Additionally, intermediate components to be further formed with insulating and / or conductive layers during the manufacture of a circuit board are also included in the term "inner layer substrate." Furthermore, inner layer substrates with built-in components may also be used.

[0779] From the viewpoint of effectively utilizing the advantage of suppressing the formation of large particles due to the leaching of components from the resin varnish, it is preferable that the circuit board using the resin composition described in the above embodiments has a small minimum line width and line spacing (L / S) for the circuit wiring. Unless otherwise stated, "line width" refers to the width of the circuit wiring, and "line spacing" refers to the width of the spacing between the wirings. The minimum line width / line spacing ratio is preferably 10 μm / 10 μm or less, more preferably 5 μm / 5 μm or less, further 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 further preferably 1 μm / 1 μm or more. In addition, the wiring spacing is preferably 20 μm or less, more preferably 10 μm or less, further preferably 6 μm or less, preferably 0.2 μm or more, more preferably 1 μm or more, and further preferably 2 μm or more. The line width and line spacing (L / S) and the wiring spacing can be uniform or non-uniform throughout the entire conductor layer.

[0780] Forming a resin composition layer on an inner substrate can be performed, for example, by a method that includes coating the inner substrate with a resin composition such as a resin varnish and drying it as needed, but it is preferable to use a resin sheet. The method for forming a resin composition layer using a resin sheet typically involves laminating the resin sheet to the inner substrate. The lamination of the resin sheet to the inner substrate can be performed by bonding the resin composition layer of the resin sheet to the inner substrate. This lamination can be performed, for example, by heating and pressing the resin sheet onto the inner substrate from the support side. Examples of components for heating and pressing the resin sheet onto the inner substrate (hereinafter also referred to as "heat-pressing components") include, for example, heated metal plates (SUS end plates, etc.) or metal rollers (SUS rollers). It should be noted that it is preferable not to press the heat-pressing component directly onto the resin sheet, but rather to press it through an elastic material such as heat-resistant rubber, so that the resin sheet fully follows the surface irregularities of the inner substrate.

[0781] The lamination of the inner substrate and the resin sheet can be performed using vacuum lamination. In vacuum lamination, the heating and pressing temperature is preferably in the range of 60°C to 160°C, more preferably 80°C to 140°C; the heating and pressing pressure is preferably in the range of 0.098 MPa to 1.77 MPa, more preferably 0.29 MPa to 1.47 MPa; and the heating and pressing time is preferably in the range of 20 seconds to 400 seconds, more preferably 30 seconds to 300 seconds. Lamination can preferably be performed under reduced pressure conditions of 26.7 hPa or less.

[0782] Lamination can be performed using commercially available vacuum laminators. 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 intermittent vacuum pressure laminators.

[0783] A method for manufacturing a circuit board may include: after lamination, pressing a heated bonding member under normal pressure (atmospheric pressure), for example from the support side, to smooth the resin sheet. The pressing conditions for the smoothing treatment may be set to the same conditions as the heated bonding conditions for the lamination described above. The smoothing treatment may be performed using a commercially available laminator. Lamination and smoothing treatment may be performed continuously using the aforementioned commercially available vacuum laminator.

[0784] The method for manufacturing the circuit board involved in this example includes a step (II) after step (I) to cure the resin composition layer. By curing the resin composition layer in step (II), an insulating layer can be formed as a cured layer containing the resin composition.

[0785] The curing of the resin composition layer is typically performed by heat curing. The heat curing conditions of the resin composition layer can 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. Furthermore, the curing time is preferably 5 minutes to 120 minutes, more preferably 10 minutes to 100 minutes, and even more preferably 15 minutes to 100 minutes.

[0786] The method for manufacturing a circuit board may include preheating the resin composition layer at a temperature lower than the curing temperature before thermally curing it. For example, before thermally curing the resin composition layer, it may typically be preheated at a temperature of 50°C to 150°C, preferably 60°C to 140°C, more preferably 70°C to 130°C, for at least 5 minutes, 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). Additionally, when a smoothing treatment is performed after the inner layer substrate and the resin sheet are laminated, preheating is usually performed after the smoothing treatment.

[0787] When using a resin sheet, the method for manufacturing a circuit board may include a step of peeling off a support for the resin sheet after the inner layer substrate and the resin sheet are laminated. The peeling off of the support may be performed between steps (I) and (II), or after step (II). Furthermore, as described later, when the method for manufacturing a circuit board includes a step (III) of forming holes in an insulating layer, a step (IV) of roughening the insulating layer, and a step (V) of forming a conductor layer, the peeling off of the support may be performed between steps (II) and (III), between steps (III) and (IV), or between steps (IV) and (V).

[0788] The manufacturing method of the circuit board may include a step (III) after step (II) of forming holes such as vias and through-holes on the insulating layer. The method of forming the holes may be selected based on 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 a laser after the support is peeled off, or holes may be formed by irradiating the insulating layer with a laser through the support. The size and shape of the holes may be appropriately determined according to the design of the circuit board.

[0789] A method for manufacturing a circuit board may include a step (IV) of roughening an insulating layer. The roughening process roughens the surface of the insulating layer. Furthermore, the roughening process removes contaminants (resin residue) from the insulating layer. Therefore, this roughening process is sometimes referred to as a "decontamination treatment." For example, if a hole is formed in step (III), contaminants may form within the hole; therefore, it is preferable to perform the roughening process (IV) after step (III) to remove the contaminants.

[0790] There are no particular limitations on the steps and conditions of the roughening treatment; known steps and conditions commonly used in forming the insulating layer of a circuit board can be adopted. For example, a wet method can be used, such as a dry method with plasma, to sequentially perform a swelling treatment based on a swelling solution, an oxidation treatment based on an oxidant, and a neutralization treatment based on a neutralization solution on the insulating layer, in order to perform the roughening treatment.

[0791] 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. Commercially available swelling solutions include, for example, "Swelling Dip Securiganth P" and "Swelling Dip Securiganth SBU" manufactured by Atotech Japan. Swelling treatment based on the swelling solution can be performed, 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 in the insulating layer to a suitable level, it is preferable to immerse the insulating layer in a swelling solution at 40°C to 80°C for 5 to 15 minutes.

[0792] Examples of oxidants used for roughening treatment include alkaline permanganate solutions obtained by dissolving potassium permanganate or sodium permanganate in an aqueous solution of sodium hydroxide. Oxidation treatment based on alkaline permanganate solutions or similar oxidants is preferably performed by immersing the insulating layer in an oxidant solution heated to 60°C to 100°C for 10 to 30 minutes. Furthermore, the concentration of permanganate in the alkaline permanganate solution is preferably 5% to 10% by mass. Commercially available oxidants include, for example, alkaline permanganate solutions such as "Concentrate Compact CP" and "Dosing Solution Securiganth P" manufactured by Atotech Japan.

[0793] As the neutralizing solution for the roughening treatment, an acidic aqueous solution is preferred. Commercially available products include, for example, "Reduction Solution Securiganth P" manufactured by Atotech Japan. Neutralization treatment based on the neutralizing solution can be performed by immersing the treated surface, which has undergone oxidative treatment based on an oxidant, in a neutralizing solution at 30°C to 80°C for 5 to 30 minutes. From an operational point of view, it is preferable to immerse the object that has undergone oxidative treatment in a neutralizing solution at 40°C to 70°C for 5 to 20 minutes.

[0794] Examples of dry decontamination treatments include plasma-based decontamination treatments. Regarding plasma-based decontamination treatments, plasma generated by introducing gas into a plasma generator is used to treat the insulating layer, thereby removing contaminants generated within the holes. There are no particular limitations on the method of plasma generation; examples include microwave plasma (generated by microwaves), high-frequency plasma (using high frequencies), atmospheric pressure plasma (generated at atmospheric pressure), and vacuum plasma (generated in a vacuum), with vacuum plasma (generated in a vacuum) being preferred.

[0795] The type of gas used in dry decontamination treatment (the type of gas used in plasma treatment) is not particularly limited as long as it can remove contaminants from the orifice. For example, a gas containing fluorine atoms or a gas containing either N2 or O2 is preferred. Examples of gases containing fluorine atoms include F2, CF4, C2F6, and SF6. In this case, in addition to a gas containing fluorine atoms, any one of N2 and O2, other gases such as Ar may also be included. From the viewpoint of improving contaminant removal performance, a gas containing fluorine atoms or any one of N2 and O2 is preferred, a gas containing fluorine atoms and O2 is more preferred, a mixture of O2 and at least one of N2 and CF4 is even more preferred, and a mixture of O2 and CF4 is particularly preferred.

[0796] When using a mixed gas as the gas type, from the viewpoint of improving contamination removal, the mixing ratio (containing either N2 or O2 / other gas: in 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.

[0797] There is no particular limitation on the time for dry cleaning, but it is preferably 30 seconds or more, more preferably 60 seconds or more, 90 seconds or more, or 120 seconds or more. From the viewpoint that it is easy to achieve an insulating layer with low surface roughness after cleaning, the upper limit of the dry cleaning time is preferably 10 minutes or less, more preferably 5 minutes or less.

[0798] Dry cleaning can be performed using commercially available dry cleaning equipment. Examples of commercially available dry cleaning equipment suitable for circuit board manufacturing include: plasma dry etching equipment manufactured by Oxford Instruments, microwave plasma equipment manufactured by NISSHIN, and atmospheric pressure plasma etching equipment manufactured by Sekisui Chemicals.

[0799] A method for manufacturing a circuit board may include a step (V) of forming a conductor layer on an insulating layer. In cases where the method for manufacturing a circuit board includes step (III) or (IV), the step (V) of forming the conductor layer is generally preferably performed after steps (III) and (IV).

[0800] There are no particular limitations on the conductor material used for the conductor layer. In a suitable embodiment, the conductor layer comprises one or more metals selected from gold, platinum, palladium, silver, copper, aluminum, cobalt, chromium, zinc, nickel, titanium, tungsten, iron, tin, and indium. The conductor layer can be a single metal layer or an alloy layer. Examples of alloy layers include layers formed from alloys of two or more metals selected from the above (e.g., nickel-chromium alloys, copper-nickel alloys, and copper-titanium alloys). From the viewpoints of versatility in conductor layer formation, cost, and ease of patterning, single metal layers of chromium, nickel, titanium, aluminum, zinc, gold, palladium, silver, or copper, or alloy layers of nickel-chromium alloys, copper-nickel alloys, or copper-titanium alloys, are preferred. Single metal layers of chromium, nickel, titanium, aluminum, zinc, gold, palladium, silver, or copper, or alloy layers of nickel-chromium alloys, are more preferred. Single metal layers of copper are even more preferred.

[0801] The conductor layer can have a single-layer structure or a multi-layer structure comprising two or more single-metal layers or alloy layers containing different types of metals or alloys. In the case of a multi-layer conductor layer, it is preferable that the layer in contact with the insulating layer is a single-metal layer of chromium, zinc, or titanium, or an alloy layer of nickel-chromium alloy.

[0802] The thickness of the conductor layer depends on the design of the circuit board, and is preferably 3μm to 35μm, more preferably 5μm to 30μm.

[0803] The conductor layer can be formed by electroplating. For example, a conductor layer with a desired wiring pattern can be formed by electroplating the surface of the insulating layer using conventional techniques such as semi-additive and fully additive methods. From the viewpoint of ease of manufacturing, the semi-additive method is preferred. An example of forming a conductor layer using the semi-additive method is shown below.

[0804] First, an electroless plating layer (electroplating 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. Then, the unwanted electroless plating layer is removed by etching, forming a conductor layer with the desired wiring pattern.

[0805] As another example, the conductor layer can be formed using metal foil. When forming the conductor layer using metal foil, step (V) is suitable to be performed between steps (I) and (II). For example, after step (I), the support is removed, and metal foil is laminated onto the surface of the exposed resin composition layer. The lamination of the resin composition layer and the metal foil can be performed by vacuum lamination. The lamination conditions can be the same as those described for step (I). Next, step (II) is performed to form an insulating layer. Then, using the metal foil on the insulating layer, a conductor layer with the desired wiring pattern can be formed using known techniques such as subtractive processing or modified semi-additive processing. Metal foil can be manufactured, for example, by known methods such as electrolysis or rolling. Commercially available metal foils include, for example, HLP foil and JXUT-III foil manufactured by JX Metals Corporation; and 3EC-III foil and TP-III foil manufactured by Mitsui Mining & Metals Corporation.

[0806] When a conductor layer is formed on an insulating layer, the method for manufacturing a circuit board may include annealing the conductor layer after its formation. Annealing can improve the adhesion between the insulating layer and the conductor layer. Annealing can be performed, for example, by heating at 150°C to 210°C for 20 to 180 minutes.

[0807] In another embodiment, the conductor layer can be formed by sputtering. When forming the conductor layer by sputtering, typically, a conductor seed layer is formed on the insulating layer by sputtering, and then a conductor sputtered layer is formed on the conductor seed layer by sputtering. Furthermore, before forming the conductor seed layer by sputtering, the surface of the insulating layer can be cleaned by backsputtering. Ar, O2, and N2 gases are preferred as backsputtering gases. When the conductor seed layer is Cu and a Cu alloy, Ar, O2, or a mixture of Ar and O2 gases are preferred. When the conductor seed layer is Ti, Ar, N2, or a mixture of Ar and N2 gases are preferred. Moreover, when the seed layer is Cr and a Cr alloy (nickel-chromium alloy, etc.), Ar, O2, or a mixture of Ar and O2 gases are preferred. Sputtering can be performed using various sputtering apparatuses such as magnetron sputtering and MirrorTron sputtering. Examples of metals forming the conductor seed layer include Cr, Ni, Ti, and nickel-chromium alloys. Cr and Ti are particularly preferred. The thickness of the conductor seed layer is preferably 5 nm or more, more preferably 10 nm or more, more preferably 1000 nm or less, and even more preferably 500 nm or less. Examples of metals forming the conductor sputtering layer include Cu, Pt, Au, and Pd. Cu is particularly preferred. The thickness of the conductor sputtering layer is preferably 50 nm or more, more preferably 100 nm or more, more preferably 3000 nm or less, and even more preferably 1000 nm or less.

[0808] In the method for manufacturing circuit boards, each of the above-mentioned processes may be performed only once or may be repeated two or more times. For example, processes (I) to (V) may be repeatedly performed to form a circuit board with a multilayer structure, such as a multilayer printed wiring board having multiple insulating layers and conductor layers.

[0809] The method for manufacturing a circuit board may further include optional steps in combination with the steps described above. For example, the method for manufacturing a circuit board may include a step of setting a semiconductor chip in a manner that bonds it to a conductor layer. As a specific example, in the case of manufacturing a circuit board for a semiconductor chip package containing a semiconductor chip, the method for manufacturing the circuit board may include a step of setting the semiconductor chip. The conditions for setting the semiconductor chip may employ appropriate conditions that enable conductive connection between the terminal electrodes of the semiconductor chip and the conductor layer formed on the insulating layer. For example, the conditions used in flip chip mounting may be employed. In addition, the semiconductor chip may be bonded via an insulating adhesive or by reflow soldering. Moreover, if necessary, the set semiconductor chip may be filled with a molding underfill material. Furthermore, the method for manufacturing a circuit board may include, for example, a step of forming a sealing layer; a step of forming a solder resist layer; and a step of cutting the manufactured circuit board into single pieces.

[0810] Examples of circuit boards include printed wiring boards and semiconductor chip packages. Examples of semiconductor chip packages include FC-CSP, MIS-BGA packages, ETS-BGA packages, fan-out WLP (Wafer Level Package), fan-in WLP, fan-out PLP (Panel Level Package), and fan-in PLP. In these semiconductor chip packages, it is preferable to use a cured product formed by curing the aforementioned resin composition to form a rewiring layer as an insulating layer. However, the circuit board is not limited to the substrate in this example.

[0811] Semiconductor Devices

[0812] The circuit board described above can be used to manufacture semiconductor devices. Semiconductor devices include the aforementioned circuit board. Examples of semiconductor devices include various semiconductor devices for use in electronic products (e.g., computers, mobile phones, smartphones, tablets, wearable devices, digital cameras, medical devices, and televisions) and vehicles (e.g., motorcycles, automobiles, electric trains, ships, and airplanes).

[0813] Example

[0814] The present invention will now be specifically described with reference to the embodiments shown below. However, the present invention is not limited to the embodiments described below.

[0815] In the following description, unless otherwise specified, "parts" and "%" refer to "parts by mass" and "% by mass," respectively. Additionally, unless otherwise specified, the temperature and pressure conditions are room temperature (23°C) and atmospheric pressure (1 atm).

[0816] <Synthetic Example 1: Synthesis of Compound A-1 containing a specific structural unit and a specific terminal group>

[0817] 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 into a flask equipped with a stirrer. N-methyl-2-pyrrolidone (113.92 g) was added, and the mixture was reacted at 130 °C for 6 hours under a nitrogen atmosphere. After the reaction, chloromethylstyrene (27.95 g) was added dropwise while the container was cooled to 10 °C, and the mixture was reacted at 65 °C for 6 hours.

[0818] N-methyl-2-pyrrolidone (258.1 g) was added to the resulting reaction solution to dilute it. Salts were removed from the diluted reaction solution by filtration. The desalted solution was then added to methanol (4960 g). The precipitated solid was filtered off, washed with a small amount of methanol, filtered again, and recovered. The recovered solid was dried under reduced pressure at 80 °C for 12 hours using a vacuum dryer, thereby obtaining compound A-1 (yield 100.40 g, 92%) represented by the following formula. The weight-average molecular weight (Mw) of compound A-1 is 3,300. Compound A-1 corresponds to the composition described above (A-1). In the following formula, n a1 The range is 0 to 5.

[0819] [Chemical Formula 49]

[0820]

[0821] <Synthetic Example 2: Synthesis of Compound A-2 containing a specific structural unit and a specific terminal group>

[0822] The starting materials and alkali metal compound 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), but the synthesis was carried out according to the same steps as in Synthesis Example 1. Through this operation, compound A-2 (93.06 g, yield 89%), represented by the following formula, was obtained. The weight-average molecular weight (Mw) of compound A-2 was 3,100. Compound A-2 is equivalent to the composition of (A-1) described above. In the following formula, n a21 n is 0 to 5.a22 The range is 0 to 5.

[0823] [Chemical Formula 50]

[0824]

[0825] <Synthetic Example 3: Synthesis of Compound A-3 containing a specific structural unit and a specific terminal group>

[0826] 33.85 g of 1,1-bis(4-hydroxy-3-methylphenyl)-3,3,5-trimethylcyclohexane, 16.66 g of 4,6-dichloro-2-phenylpyrimidine, and 18.66 g of potassium carbonate were weighed into a flask equipped with a stirrer. 42.50 g of N-methyl-2-pyrrolidone was added, and the mixture was reacted at 100 °C for 6 hours under a nitrogen atmosphere. After the reaction, 8.680 g of chloromethylstyrene was added dropwise to the container while it was cooled to 10 °C, and the mixture was then reacted at 100 °C for 4 hours.

[0827] N-methyl-2-pyrrolidone (42.50 g) was added to the resulting reaction solution to dilute it. Salts were removed from the diluted reaction solution by filtration. The desalted solution was then added to methanol (6900 g). The precipitated solid was filtered off, washed with a small amount of methanol, filtered again, and recovered. The recovered solid was dried under reduced pressure at 60 °C for 12 hours using a vacuum dryer, thereby obtaining compound A-3 (yield 44.10 g, 90%) represented by the following formula. The weight-average molecular weight (Mw) of compound A-3 is 3,400. Compound A-3 is equivalent to the composition described above (A-1). In the following formula, n a3 The range is 0 to 5.

[0828] [Chemical Formula 51]

[0829]

[0830] <Synthetic Example 4: Synthesis of Compound A-4 containing a specific structural unit and a specific terminal group>

[0831] The starting materials and alkali metal compounds 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), and the synthesis was carried out according to the same procedure as in Synthesis Example 3. Through this operation, compound A-4, represented by the following formula (a-4), was obtained (yield 89.30 g, 90%). The weight-average molecular weight (Mw) of compound A-4 was 4,000. Compound A-4 is equivalent to the composition described in (A-1) above. In the following formula, n a4 The range is 0 to 5.

[0832] [Chemical Formula 52]

[0833]

[0834] In equation (a-4), R X It represents the divalent group represented by formula (X-1) or the divalent group represented by formula (X-2).

[0835] [Chemical Formula 53]

[0836]

[0837] In equations (X-1) and (X-2), the wavy line represents the bonding site.

[0838] <Synthetic Example 5: Synthesis of Compound A-5 containing a specific structural unit and a specific terminal group>

[0839] The starting materials and alkali metal compounds were changed to 2,2-bis(4-hydroxy-3-methylphenyl)propane (51.27 g), 4,4'-(2-hydroxybenzyl)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), and the synthesis was carried out according to the same steps as in Synthesis Example 1. Through this operation, compound A-5 (108.17 g, 89% yield) having the structural units represented by the following formulas (a-5-1) and (a-5-2) was obtained. Compound A-5 contains a vinylbenzyl group at the end. The weight-average molecular weight (Mw) of compound A-5 is 4,200. Compound A-5 corresponds to the composition described in (A-2) above.

[0840] [Chemical Formula 54]

[0841]

[0842] In equations (a-5-1) and (a-5-2), ★ indicates a bond with any ★★.

[0843] <Synthetic Example 6: Synthesis of Compound A-6 containing a specific structural unit and a specific terminal group>

[0844] The starting materials and alkali metal compounds 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), and the synthesis was carried out according to the same procedure as in Synthesis Example 1. Through this operation, compound A-6 (110.00 g, 92% yield) having the structural units represented by formulas (a-6-1) and (a-6-2) was obtained. Compound A-6 contains a vinylbenzyl group at the end. The weight-average molecular weight (Mw) of compound A-6 is 4,100. Compound A-6 corresponds to the composition described in (A-2) above.

[0845] [Chemical Formula 55]

[0846]

[0847] In equations (a-6-1) and (a-6-2), ★ indicates a bond with any ★★.

[0848] <Synthetic Example 7: Synthesis of Compound A-7 containing a specific structural unit and a specific terminal group>

[0849] The starting materials and alkali metal compounds 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)tetra(2-methylphenol) (31.63 g), 4,6-dichloro-2-phenylpyrimidine (41.43 g), potassium carbonate (55.98 g), and chloromethylstyrene (49.15 g), and the synthesis was carried out according to the same procedure as in Synthesis Example 1. By this operation, compound A-7 (133.27 g, 88% yield) having the structural units represented by formulas (a-7-1) and (a-7-2) was obtained. The weight-average molecular weight (Mw) of compound A-7 was 17,900. Compound A-7 corresponds to the composition described in (A-2) above.

[0850] [Chemical Formula 56]

[0851]

[0852] In equations (a-7-1) and (a-7-2), ★ indicates a bond with any ★★.

[0853] <Synthetic Example 8: Synthesis of Compound A-8 containing a specific structural unit but lacking a specific terminal group>

[0854] 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane (18.60 g), 4,6-dichloro-2-phenylpyrimidine (13.70 g) and potassium carbonate (11.40 g) were measured into a flask equipped with a stirrer, and N-methyl-2-pyrrolidone (75 g) was added. The mixture was reacted at 130 °C for 6 hours under a nitrogen atmosphere.

[0855] N-methyl-2-pyrrolidone (368 g) was added to the resulting reaction solution to dilute it. Salts were removed from the diluted reaction solution by filtration. The desalted solution was then added to methanol (9100 g). The precipitated solid was filtered off, washed with a small amount of methanol, filtered again, and recovered. The recovered solid was dried under reduced pressure at 120 °C for 12 hours using a vacuum dryer, thereby obtaining compound A-8 (20.5 g, 90% yield) having the structural unit represented by the following formula. Compound A-8 contains a phenolic hydroxyl group at the terminal. The weight-average molecular weight (Mw) of compound A-8 is 187,000. Compound A-8 is neither equivalent to component (A-1) nor component (A-2) described above. In the following formula, n a8 It is above 0.

[0856] [Chemical Formula 57]

[0857]

[0858] <Synthetic Example 9: Synthesis of Maleimide Resin B-1>

[0859] A MEK solution (62% by mass) of maleimide resin (Mw / Mn = 1.81, t” = 1.47 (mainly 1, 2 or 3)) synthesized using the method described in Synthesis Example 1 of Japan Invention Association Publication No. 2020-500211 was prepared. This maleimide resin B-1 has the structure represented by the following formula.

[0860] [Chemical Formula 58]

[0861]

[0862] <Synthetic Example 10: Synthesis of Maleimide Resin B-2>

[0863] (I) Synthesis of intermediate amine compound B'-2

[0864] 2-Ethylaniline (242.4 g, 2.0 mol), xylene (242 g), and activated clay (80 g) were added to a flask equipped with a thermometer, cooling tube, Dean-Stark separator, and stirrer. The mixture was heated to 130 °C while stirring and maintained for 30 minutes. Then, DVB-810 (a mixture of divinylbenzene / ethylstyrene (divinylbenzene / ethylstyrene = 81 / 19 (mol)%), manufactured by JITIC Chemical Materials) (272.0 g) was added dropwise over 2 hours, and the reaction was carried out directly for 1 hour. Afterward, the temperature was raised to 190 °C over 6 hours and maintained for 10 hours. Following the reaction, the mixture was cooled to 100 °C in air, diluted with 300 g of toluene, and the activated clay was removed by filtration. The solvent and unreacted low molecular weight substances were then distilled off under reduced pressure to obtain the intermediate amine compound B'-2. The amine equivalent of intermediate amine compound B'-2 was 214 g / eq.

[0865] (II) Synthesis of maleimide resin B-2 (maleimidization)

[0866] Maleic anhydride (117.7 g, 1.2 mol) and toluene (700 g) were added to a 2 L flask equipped with a thermometer, cooling tube, Dean-Stark separator, and stirrer, and stirred at room temperature. Next, a mixed solution of intermediate amine compound B'-2 (214 g, 1 equivalent) and dimethylformamide (175 g) was added dropwise over 1 hour, followed by a reaction time of 2 hours. p-Toluenesulfonic acid monohydrate (37.1 g) was added to the reaction mixture, and the mixture was heated to 115 °C. After cooling and separating the azeotropic water and toluene under reflux, only toluene was returned to the system for a dehydration reaction over 5 hours. After cooling to room temperature with air, the mixture was neutralized with 49% NaOH. Then, toluene and water were removed by vacuum distillation at 60 °C, and MEK (methyl ethyl ketone) (600 g) was added to the remaining DMF solution in the flask. The solution was heated to 60°C and then subjected to three separate-liquid treatments with ion-exchanged water (200g) to remove salts. Sodium sulfate was then added and the solution dried under reduced pressure. The resulting reactants were then vacuum-dried at 80°C to obtain maleimide resin B-2.

[0867] <Synthetic Example 11: Synthesis of Maleimide Resin B-3>

[0868] (I) Synthesis of intermediate amine compound B'-3

[0869] 400 g (3.3 mol) of 2-ethylaniline, 127 g of a compound with a benzyl ether skeleton ("NIKANOL L" manufactured by Fudow), 193 g of toluene, and 53 g of activated clay were added to a flask equipped with a thermometer, cooling tube, Dean-Stark separator, and stirrer. The mixture was heated to 120 °C while stirring and held for 30 minutes. Then, the temperature was increased to 150 °C and held for 3 hours. After holding, the temperature was increased to 200 °C over 30 minutes and held for 10 hours. After holding, the mixture was diluted with toluene (193 g), and the activated clay was separated by filtration. The filtrate was distilled off by heating under reduced pressure to remove the solvent and excess 2-ethylaniline, yielding the intermediate amine compound B'-3. The amine equivalent of intermediate amine compound B'-3 was 209 g / eq.

[0870] (II) Synthesis of maleimide resin B-3 (maleimidization)

[0871] Maleic anhydride (73.2 g, 126 mol, 1.3 equivalents) and toluene (461 g) were added to a 2 L flask equipped with a thermometer, cooling tube, Dean-Stark separator, and stirrer, and stirred at room temperature. Next, a mixed solution of intermediate amine compound B'-2 (209 g, 1 equivalent) and dimethylformamide (57.7 g) was added dropwise over 1 hour, followed by a reaction time of 2 hours. Then, p-toluenesulfonic acid monohydrate (9.72 g) was added to the reaction mixture. The reaction mixture was heated, and the azeotropic water and toluene were cooled and separated under reflux. The mixture was then heated to 115 °C, and the azeotropic water and toluene were cooled and separated under reflux, with only toluene returned to the system for a dehydration reaction over 5 hours. After cooling the air to room temperature, the solution was concentrated under reduced pressure to dissolve the brown solution in ethyl acetate (600 g). The solution was washed three times with ion-exchanged water (200 g) and three times with a 2% sodium bicarbonate aqueous solution (150 g). Sodium sulfate was added and the solution was dried. The solution was then concentrated under reduced pressure. The resulting reactants were dried under vacuum at 80 °C for 4 hours to obtain a product containing maleimide resin B-3 (a solution of 62% by mass of non-volatile components).

[0872] <Synthesis Example 12: Synthesis of Polyimide Resin E>

[0873] In a solvent, N,N-dimethylacetamide (DMAc) (400 g), 2,2-bis[4-(3,4-dicarboxyphenoxy)phenyl]propane dianhydride (BPADA) (46.5 g), 4,4'-[1,4-phenylenebis[(1-methylethoxy)-4,1-phenyleneoxy]]bisphenylamine (BPPAN) (37.8 g), dimeric diamine ("PRIAMINE 1075" manufactured by Croda Japan) (12.8 g), 5-norbornene-2,3-dicarboxylic anhydride (1.9 g), and toluene (40 g) were mixed. The resulting monomer composition was stirred at room temperature and atmospheric pressure for 3 hours to allow it to react. This yielded a solution of polyamic acid.

[0874] Next, the polyamic acid solution was heated to approximately 160°C, and the condensed water was azeotropically removed with toluene under a nitrogen stream. It was confirmed that a specified amount of water accumulated in the moisture metering receiver and that no water flow was observed. After confirmation, the reaction solution was further heated and stirred at 200°C for 1 hour. It was then cooled. This yielded a varnish containing terminal olefin-modified polyimide resin E (20% by mass of non-volatile components).

[0875] <Examples 1-53, Comparative Examples 1-8: Preparation of Resin Compositions>

[0876] Each component was weighed according to the mass proportions listed in Tables 1 and 2 below, and uniformly dispersed using a high-speed rotary mixer to obtain a varnish-like resin composition. Details of each component listed in Tables 1 and 2 are as follows.

[0877] (A) Compounds containing specific structural units and specific terminal groups:

[0878] Synthesis Example 1: Compound A-1 obtained in Synthesis Example 1

[0879] Synthesis Example 2: Compound A-2 obtained in Synthesis Example 2

[0880] Synthesis Example 3: Compound A-3 obtained in Synthesis Example 3

[0881] Synthesis Example 4: Compound A-4 obtained in Synthesis Example 4

[0882] Synthesis Example 5: Compound A-5 obtained in Synthesis Example 5

[0883] Synthesis Example 6: Compound A-6 obtained in Synthesis Example 6

[0884] Synthesis Example 7: Compound A-7 obtained in Synthesis Example 7

[0885] (A') Compounds containing specific terminal groups but not specific structural units:

[0886] “OPE-2St”: Vinyl benzyl modified polyphenylene ether, manufactured by Mitsubishi Gas Chemical Co., Ltd., a toluene solution with 65% by weight of non-volatile components.

[0887] (A”) Compounds containing a specific structural unit but not a specific terminal group:

[0888] Synthesis Example 8: Compound A-8 obtained in Synthesis Example 8

[0889] (B) Maleimide resin:

[0890] “MIR-3000-70MT”: Aromatic maleimide resin, manufactured by Nippon Kayaku Co., Ltd., a 70% by weight MEK-toluene mixed solution containing non-volatile components.

[0891] “MIR-5000-60T”: Aromatic maleimide resin, manufactured by Nippon Kayaku Co., Ltd., a toluene solution containing 60% by weight of non-volatile components.

[0892] Synthesis Example 9: Maleimide resin B-1 obtained in Synthesis Example 9, MEK solution with 62% by mass of non-volatile components.

[0893] Synthesis Example 10: Maleimide resin B-2 obtained in Synthesis Example 10

[0894] Synthesis Example 11: A solution of maleimide resin B-3 obtained in Synthesis Example 11, containing 62% by mass of non-volatile components.

[0895] "BMI-689": Aliphatic maleimide resin, manufactured by Desinger Molecules Inc., containing an N-alkyl bismaleimide backbone derived from a dimeric diamine.

[0896] "BMI-1500": Aliphatic maleimide resin, manufactured by Desinger Molecules Inc., containing an N-alkyl bismaleimide backbone derived from dimeric diamine.

[0897] (C) Flame retardant:

[0898] "FP-72TP": Phosphorus content 14.4% by mass, manufactured by Fushimi Pharmaceutical Co., Ltd.

[0899] The following formula represents cyclic phosphazene compounds:

[0900] [Chemical Formula 59]

[0901]

[0902] "FP-700": Phosphorus content 12.7% by mass, manufactured by Fushimi Pharmaceutical Co., Ltd.

[0903] "FP-100": Phosphorus content 13.4% by mass, manufactured by Fushimi Pharmaceutical Co., Ltd.

[0904] "PQ-60": Phosphorus content 11% by mass, manufactured by Jin Yi Chemical Company.

[0905] "PX-200": Phosphorus content 9% by mass, manufactured by Daiba Chemical Industry Co., Ltd.

[0906] "SR-3000": Phosphorus content 7% by mass, manufactured by Daiba Chemical Industry Co., Ltd.

[0907] "BO-1001": Phosphorus content 1.8% by mass, manufactured by Nippon Soda Co., Ltd.

[0908] "VP-1": Phosphorus content 7.5wt%, manufactured by Shikoku Chemical Industry Co., Ltd.

[0909] The following formula represents the compound:

[0910] [Chemical Formula 60]

[0911]

[0912] "HCA-HQ-HST": Phosphorus content 10% by mass, manufactured by Sanguang Company.

[0913] (D) Inorganic filler materials:

[0914] “Inorganic filler material 1”: Spherical solid silica (SO-C2 manufactured by Admatechs, with an average particle size of 0.5 μm and a specific surface area of ​​5.8 m²). 2 / g) Material obtained by surface treatment with an amine-based silane coupling agent ("KBM573" manufactured by Shin-Etsu Chemical Co., Ltd.)

[0915] “Inorganic Filler Material 2”: A material obtained by surface treatment of spherical hollow silica particles (“LHP-208” manufactured by UBE EXSYMO, with an average particle size of 0.5 μm and an average porosity of 50% by volume) with an amine silane coupling agent (“KBM-573” manufactured by Shin-Etsu Chemical Co., Ltd.)

[0916] “Inorganic Filler Material 3”: A material obtained by surface treatment of spherical hollow aluminum silicate particles (“MGH-005” manufactured by Pacific Cement Corporation, with an average particle size of 1.6 μm and an average porosity of 80% by volume) with an amine silane coupling agent (“KBM-573” manufactured by Shin-Etsu Chemical Industry Co., Ltd.)

[0917] "Inorganic filler material 4": Spherical solid silica particles (DENKA's "UFP-30", average particle size 0.3μm, specific surface area 30.7m²). 2 / g) The material obtained by surface treatment with an amine-based silane coupling agent ("KBM-573" manufactured by Shin-Etsu Chemical Industry Co., Ltd.)

[0918] (E) Thermoplastic resins:

[0919] "Synthesis Example 12": A solution of polyimide resin E obtained in Synthesis Example 12, containing 20% ​​by mass of non-volatile components.

[0920] "P2000": Hydrogenated styrene-based thermoplastic elastomer, manufactured by Asahi Kasei Corporation.

[0921] “YX7891T30”: Phenoxy resin, manufactured by Mitsubishi Chemical Corporation, a toluene solution containing 30% by weight of non-volatile components.

[0922] (F) Curing accelerator:

[0923] "1B2PZ": Imidazole-based curing accelerator (1-benzyl-2-phenylimidazolium), manufactured by Shikoku Chemical Industry Co., Ltd.

[0924] "2P4MZ": Imidazole-based curing accelerator (2-phenyl-4-methylimidazole), manufactured by Shikoku Chemical Industry Co., Ltd.

[0925] "2E4MZ": Imidazole-based curing accelerator (2-ethyl-4-methylimidazole), manufactured by Shikoku Chemical Industry Co., Ltd.

[0926] Luperox DTA: Peroxide-based free radical polymerization initiator (di-tert-amyl peroxide), manufactured by ARKEMAYoshitomi Ltd.

[0927] (G) Liquid thermosetting resin

[0928] “ALP-d”: bis[3-allyl-4-(3,4-dihydro-2H-1,3-benzo[]] [Zinaz-3-yl)phenyl]methane, manufactured by Shikoku Chemical Industry Co., Ltd.

[0929] "TAIC": Triallyl isocyanurate, manufactured by Nippon Chemical Co., Ltd.

[0930] "DCP": Tricyclodecanedimethylethanol dimethacrylate, manufactured by Shin-Nakamura Chemical Industry Co., Ltd.

[0931] "WA": Modified aromatic amine, manufactured by Mitsubishi Chemical Corporation.

[0932] <Preparation of Resin Sheet A>

[0933] As a support, a polyethylene terephthalate film (Lumirror R80 manufactured by Toray Industries, 38 μm thick, softening point 130°C) that had been molded with an alkyd resin-based release agent (AL-5 manufactured by LINTEC) was prepared.

[0934] Using a die coater, the resin compositions obtained in the examples and comparative examples were uniformly coated onto the support to make the thickness of the dried resin composition layer 40 μm, and dried at 70°C to 90°C for 3 minutes, thereby forming a resin composition layer on the support.

[0935] Next, on the surface of the resin composition layer that is not bonded to the support, the rough surface of a polypropylene film (ALFAN MA-411 manufactured by Oji F-Tex, 15 μm thick) serving as a protective film is laminated. Thus, a resin sheet A is obtained, consisting of a support, a resin composition layer, and a protective film arranged sequentially.

[0936] <Experimental Example 1: Determination of the Dielectric Loss Tangent>

[0937] The protective film was peeled off from the resin sheet obtained above, and the resin composition layer was heat-cured at 200°C for 90 minutes. The support was then peeled off. The resulting cured material was cut into test pieces with a width of 2 mm and a length of 80 mm as evaluation pieces.

[0938] For each test piece A, the dielectric loss tangent was measured using the HP8362B manufactured by Agilent Technologies via the cavity resonator perturbation method at a measurement frequency of 5.8 GHz and a measurement temperature of 23 °C. Measurements were performed on three test pieces, and the average value was calculated.

[0939] <Experimental Example 2: Determination of Arithmetic Mean Roughness and Peel Strength of Electroplated Conductor Layer>

[0940] (2-1) Preparation of inner layer substrate

[0941] Using a micro-etching agent (MEC's ​​"CZ8101"), the copper surface of the glass cloth substrate epoxy resin double-sided copper-clad laminate (copper foil thickness 18μm, substrate thickness 0.8mm, Panasonic's "R1515A") with inner layer circuitry was roughened by etching 1μm on both sides.

[0942] (2-2) Lamination of resin sheets

[0943] The protective film was peeled off from the resin sheet obtained in Example 1, exposing the resin composition layer. Using an intermittent vacuum pressure laminator (Nikko-Materials, 2-stage laminator "CVP700"), the resin sheet was laminated onto both sides of the inner layer substrate with the resin composition layer in contact with the inner layer substrate. The lamination was performed by depressurizing for 30 seconds to adjust the pressure to below 13 hPa, followed by pressing for 30 seconds at 100°C and 0.74 MPa. Then, a hot press was performed for 60 seconds at 100°C and 0.5 MPa. Through this operation, a laminate A was obtained, consisting of a support / resin composition layer / inner layer substrate / resin composition layer / support.

[0944] (2-3) Thermosetting of the resin composition layer

[0945] The laminate A was placed in an oven at 100°C and heated for 30 minutes, then transferred to an oven at 190°C and heated for another 30 minutes. This process thermally cured the resin composition layer, forming an insulating layer. Afterward, the support was peeled off from the laminate A, yielding a cured substrate A with a layer structure consisting of an insulating layer / inner substrate / insulating layer.

[0946] (2-4) Roughening treatment

[0947] The cured substrate A underwent a decontamination treatment as a roughening process. As a decontamination treatment, the following wet decontamination treatment was performed.

[0948] (Wet cleaning treatment)

[0949] The resulting cured substrate A was immersed in a swelling solution (Swelling Dip Securiganth P, manufactured by Atotech Japan, an aqueous solution of diethylene glycol monobutyl ether and sodium hydroxide) at 60°C for 5 minutes. Next, it was immersed in an oxidizing agent solution (Concentrate Compact CP, manufactured by Atotech Japan, an aqueous solution of approximately 6% potassium permanganate and approximately 4% sodium hydroxide) at 80°C for 15 minutes. Next, it was immersed in a neutralizing solution (Reduction Solution Securiganth P, an aqueous solution of sulfuric acid, manufactured by Atotech Japan) at 40°C for 5 minutes. Finally, it was dried at 80°C for 15 minutes. This substrate was designated "Evaluation Substrate B".

[0950] (2-5) Formation of the conductor layer

[0951] A conductor layer was formed on the roughened surface of the insulating layer of evaluation substrate B using a semi-additive method. Specifically, evaluation substrate B was immersed in an electroless plating solution containing PdCl2 at 40°C for 5 minutes, followed by immersion in an electroless copper plating solution at 25°C for 20 minutes. Next, after annealing at 150°C for 30 minutes, a resist was formed, and a pattern was etched. Then, copper sulfate electroplating was performed to form a conductor layer with a thickness of 30 μm, followed by annealing at 200°C for 90 minutes. The resulting substrate is referred to as "evaluation substrate C".

[0952] (2-6) Determination of arithmetic mean roughness (Ra)

[0953] For evaluating substrate B, a non-contact surface roughness meter (Veeco Instruments "WYKO NT3300") was used. Ra was calculated using VSI contact mode and a 50x lens, with the measurement range set to 121μm × 92μm. The average value of 10 randomly selected points was then used as the measured value.

[0954] <Determination of peel strength of electroplated conductor layer>

[0955] The peel strength between the insulation layer and the conductor layer was measured according to the Japanese Industrial Standard (JIS C6481). Specifically, a rectangular incision with a width of 10 mm and a length of 100 mm was cut into the conductor layer of the evaluation substrate C. One end was peeled off, and the substrate was held in the clamps of a tensile testing machine. The load (kgf / cm) at which 35 mm was peeled vertically at a speed of 50 mm / min was measured at room temperature, and the peel strength was determined. A tensile testing machine (TSE Corporation "AC-50C-SL") was used for the measurement.

[0956] <Experimental Example 3: Stab Test>

[0957] (3-1) Evaluation of the preparation of cured products

[0958] On the untreated side of a PET film treated with release agent on one side (LINTEC's "501010", 50μm thick, 240mm square), a double-sided copper-clad laminate of glass cloth substrate (Panasonic's "R5715ES", 0.7mm thick, 255mm square) is overlapped, and the four sides are fixed with polyimide adhesive tape (10mm wide) (hereinafter, sometimes referred to as "fixing the PET film").

[0959] Using an applicator, the resin compositions obtained in the examples and comparative examples were applied to the demolding surface of the above-mentioned "fixed PET film" so that the thickness of the dried resin composition layer was 40 μm, and dried at 70°C to 100°C for 3 minutes to obtain a resin sheet.

[0960] Next, the obtained resin sheet was placed in an oven at 200°C and heated for 90 minutes to heat-cure the resin composition layer. Then, after peeling the polyimide adhesive tape from the heat-cured resin sheet, the glass cloth substrate epoxy resin double-sided copper-clad laminate was removed, and then the PET film ("501010" manufactured by LINTEC) was peeled off, resulting in a sheet-like cured product. The obtained cured product was referred to as the "evaluation cured product".

[0961] (3-2) Stab test of cured material

[0962] The cured material for evaluation was cut into test pieces with each side approximately 30 mm in diameter. Puncture resistance tests were performed using a universal testing machine (AND Corporation, "Tensiron RTC1250A"). After mounting the test piece on the device, a needle with a load of 50 N and a diameter of 1 mm was brought into contact with the test piece at a speed of 50 mm / min, and the maximum point load at fracture was measured.

[0963] <Experimental Example 4: Determination of Glass Transition Temperature Tg>

[0964] The cured material obtained in (3-1) above was cut into test pieces approximately 5 mm wide and 15 mm long. Thermomechanical analysis was performed using a Thermo Plus TMA8310 thermomechanical analyzer (RIGAKU Corporation) via tensile loading. Specifically, after mounting the test pieces on the thermomechanical analyzer, two consecutive measurements were taken under a 1 g load and a heating rate of 5 °C / min (the first measurement was taken at 200 °C, and the second at 260 °C). The glass transition temperature Tg (°C) was then calculated based on the results of the second measurement.

[0965] <Experimental Example 5: Evaluation of Crack Resistance>

[0966] (1) Preparation of substrate

[0967] As the inner layer substrate, a core material ("E705GR" manufactured by Hitachi Chemical Industries Co., Ltd., with a diameter of 350μm and a residual copper content of 60% (copper thickness of 35μm) forming a grid pattern with 400μm intervals was prepared.

[0968] (2) Lamination of resin sheets

[0969] Using an intermittent vacuum pressure laminator (Nikko-Materials' CVP700, a two-stage laminator), the resin sheet obtained in (3-1) above (resin composition layer thickness: 40 μm) was laminated onto both sides of the inner layer substrate in a manner that bonded the resin composition layer to the inner layer substrate. The lamination was performed by depressurizing for 30 seconds to adjust the air pressure to below 13 hPa, followed by pressing for 30 seconds at 100°C and a pressure of 0.74 MPa.

[0970] (3) Thermosetting of the resin composition layer

[0971] Next, the inner layer substrate with the resin sheets stacked was placed in an oven at 100°C and heated for 30 minutes, then transferred to an oven at 190°C and heated for another 30 minutes to thermally cure the resin composition layer, forming an insulating layer. Afterward, the support was peeled off, yielding a cured substrate D with an insulating layer / inner layer substrate / insulating layer structure.

[0972] (4) Roughening treatment

[0973] The cured substrate D underwent a decontamination treatment as a roughening process. As a decontamination treatment, the following wet decontamination treatment was performed.

[0974] (Wet cleaning treatment)

[0975] The cured substrate D was immersed in a swelling solution (Swelling Dip Securiganth P, manufactured by Atotech Japan, an aqueous solution of diethylene glycol monobutyl ether and sodium hydroxide) at 60°C for 5 minutes. Next, the cured substrate D was immersed in an oxidizing agent solution (Concentrate Compact CP, manufactured by Atotech Japan, an aqueous solution of approximately 6% potassium permanganate and approximately 4% sodium hydroxide) at 80°C for 15 minutes. Then, the cured substrate D was immersed in a neutralizing solution (Reduction Solution Securiganth P, an aqueous solution of sulfuric acid, manufactured by Atotech Japan) at 40°C for 5 minutes. Afterward, it was dried at 80°C for 15 minutes. This substrate was designated as "Evaluation Substrate E".

[0976] (5) Crack evaluation

[0977] Observe the copper pad portion of 100 roughened evaluation substrates E to confirm whether there are cracks in the resin composition layer, and evaluate the crack resistance according to the following criteria.

[0978] “○”: There are fewer than 10 cracks.

[0979] "×": More than 10 cracks.

[0980] <Example 6: Evaluation of Flame Retardancy>

[0981] (1) Preparation of substrate

[0982] The copper foil etched sample (0.2 mm thick, halogen-free core) of the copper-clad laminate (“679FG”, manufactured by Resonac) was heated in an oven at 190°C for 30 minutes and then cooled to room temperature.

[0983] (2) Lamination of resin sheets

[0984] In the cooled copper foil etching, resin sheet A (resin composition layer thickness: 80 μm) obtained in the examples and comparative examples was laminated onto both sides of the substrate using an intermittent vacuum pressure laminator (Nikko-Materials' CVP700 two-stage laminator), with the resin composition layer bonded to the substrate. The lamination was performed by depressurizing for 30 seconds to bring the pressure below 13 hPa, followed by pressing for 30 seconds at 100°C and a pressure of 0.74 MPa.

[0985] (3) Curing of resin sheet A

[0986] The PET film is peeled off from the laminated resin sheet A, and the resin composition layer is thermocured by heating at 200°C for 90 minutes. This yields a substrate A with an insulating layer / inner substrate / insulating layer structure, containing a cured resin composition layer (an insulating layer with a thickness of 80 μm).

[0987] (4) Pretreatment of substrate A

[0988] The obtained substrate A was cut into pieces with a width of 12.7 mm and a length of 127 mm. The cut surfaces were then ground with sandpaper (#1200) and then with sandpaper (#2800). This yielded a substrate for flame retardancy testing.

[0989] (5) Evaluation of flame retardancy

[0990] The obtained flame retardancy test substrates were subjected to flame retardancy tests (fire resistance tests) according to UL 94 standards. The results of the flame retardancy test were as follows: if no burning residue remained after 10 seconds of exposure to a flame, the substrate was rated as "×" indicating poor fire resistance; if burning residue remained after 10 seconds of exposure to a flame, it was rated as either "V0" or "V1" according to the UL 94 standard, indicating good flame retardancy.

[0991] [Table 1]

[0992] ...

Claims

1. A resin composition comprising: (A-1) a compound containing a structural unit represented by the following formula (Al-1) and a terminal group represented by the following formula (y), (B) a maleimide resin, (C) a phosphorus-based flame retardant, and (D) an inorganic filler, wherein, the content of the (C) component is 0.1 mass% or more and 1 mass% or less when the non-volatile components in the resin composition are taken as 100 mass%, in the formula (Al-1), R 1 each independently represents a divalent nitrogen-containing heteroaromatic group which can 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 a oxygen atom and a sulfur atom, in the formula (y), Y represents a monovalent organic group having 3 to 50 carbon atoms containing a radical-polymerizable group other than a maleimide group, the wavy line represents a bonding site.

2. The resin composition of claim 1, wherein, In formula (A1-1), R 2 The group represented by the formula (A1-2) is represented by the following formula (A1-2-1) or (A1-2-2). in the formula (Al-2), Ar 1 and Ar 2 each independently represents a divalent aromatic group which can have a substituent, L each independently represents a single bond or a divalent linking group, R 4 and R 5 each independently represents a single bond or an alkylene group having 1 to 4 carbon atoms, m1 represents an integer of 0 to 5, the wavy line represents a bonding site.

3. The resin composition of claim 2, wherein, in the formula (Al-2), the group represented by L is any one of the divalent groups represented by the following formulas (Al-4-1) to (Al-4-3), in the formulas (Al-4-1) to (Al-4-3), R A21 each 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 A22 each independently represents a monovalent group selected from an alkyl group having 1 to 4 carbon atoms and an aryl group having 6 to 14 carbon atoms, m6 and m7 each independently represent an integer of 0 to 4, the wavy line represents a bonding site.

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

5. The resin composition of claim 1, wherein, the content of the (Al-1) component is 5 mass% or more and 25 mass% or less when the non-volatile components in the resin composition are taken as 100 mass%.

6. A resin composition comprising: (A-2) a compound containing a structural unit represented by the following formula (A2-1) and a terminal group represented by the following formula (y), (B) a maleimide resin, (C) a phosphorus-based flame retardant, and (D) an inorganic filler, wherein the content of the (C) component is 0.1 mass% or more and 1 mass% or less when the non-volatile components in the resin composition are taken as 100 mass%, in the formula (A2-1), R 21 each independently represents a divalent nitrogen-containing heteroaromatic group which can have a substituent, R 22 each independently represents a divalent aromatic hydrocarbon group which can have a substituent, R 23 represents a hydrocarbon group having 1 to 20 carbon atoms in which one or more groups represented by the following formula (al) are bonded, X 2 represents independently for each occurrence -O-, -S- or -N(R 24 )-, R 24 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 a oxygen atom and a sulfur atom, in the formula (a1), * represents a site bonded to a hydrocarbon having 1 to 20 carbon atoms, ** represents a site bonded to other structural units contained in the (A-2) component, R 22 and X 2 respectively, in said formula (A2-1) 22 and X 2 likewise, in the formula (y), Y represents a monovalent organic group having 3 to 50 carbon atoms containing a radical-polymerizable group other than a maleimide group, the wavy line represents a bonding site.

7. The resin composition of claim 6, wherein, In formula (A2-1) and formula (a1), R 22 each of the groups represented is independently a structure represented by the following formula (A2-2), in the formula (A2-2), * indicates the site of bonding to R 23 R1in the formula (a1) indicates the site of bonding to a hydrocarbon group having 1 to 20 carbon atoms, *** indicates the position of bonding with X in said formula (A2-1) or said formula (a1) 2 the site of bonding, R 25 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 A1 represents an integer of 0 to 2, n A2 represents an integer of 0 to 4.

8. The resin composition of claim 7, wherein, the structure represented by the formula (A2-2) is the following formula (A2-3-1) or the following formula (A2-3-2), in the formulas (A2-3-1) and (A2-3-2), R 26 each 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 A3 represents an integer of 0 to 3, n A4 represents an integer of 0 to 2, *, ***, R 25 and n A1 are synonymous with *, ***, R 25 and n A1 in said formula (A2-2), respectively, the wavy line represents a bonding site.

9. The resin composition of claim 6, wherein, the (A-2) component further contains a structural unit represented by the following formula (Al-1), in the formula (Al-1), R 1 each independently represents a divalent nitrogen-containing heteroaromatic group which can have a substituent, R 2 each independently represents a divalent organic group, X 1 represents independently for each occurrence -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 a oxygen atom and a sulfur atom.

10. The resin composition of claim 6, wherein, the weight average molecular weight (Mw) of the (A-2) component is 3,000 or more and 30,000 or less.

11. The resin composition of claim 6, wherein, the content of the (A-2) component is 5 mass% or more and 25 mass% or less when the non-volatile components in the resin composition are taken as 100 mass%.

12. The resin composition of claim 1 or 6, wherein, in the formula (y), the group represented by Y contains a monovalent aromatic group containing a radical-polymerizable group.

13. The resin composition of claim 1 or 6, wherein, in the formula (y), the group represented by Y is a vinylbenzyl group.

14. The resin composition of claim 1 or 6, wherein, the content of the (B) component is 5 mass% or more and 25 mass% or less when the non-volatile components in the resin composition are taken as 100 mass%.

15. The resin composition of claim 1 or 6, wherein, The content of the (B) component is 6.5% by mass or more and 21% by mass or less, based on 100% by mass of the nonvolatile components in the resin composition.

16. The resin composition of claim 1 or 6, wherein, The (C) component contains at least one of a phosphazene compound and a compound having a phosphine ring structure.

17. The resin composition of claim 1 or 6, wherein, The content of the (C) component is 0.01% by mass or more and 3% by mass or less, based on 100% by mass of the nonvolatile components of the resin composition layer.

18. The resin composition of claim 1 or 6, wherein, The content of the (C) component is 0.03% by mass or more and 3.5% by mass or less, based on 100% by mass of the resin components in the resin composition.

19. The resin composition of claim 1 or 6, wherein, The content of the (D) component is 60% by mass or more, based on 100% by mass of the nonvolatile components in the resin composition.

20. The resin composition of claim 1 or 6, wherein, The resin composition further contains an (E) thermoplastic resin.

21. The resin composition of claim 20, wherein, The (E) component contains at least one of a polyimide resin, a phenoxy resin, and a polystyrene resin.

22. The resin composition of claim 20, wherein, The content of the (E) component is 0.01% by mass or more and 5% by mass or less, based on 100% by mass of the nonvolatile components in the resin composition.

23. The resin composition of claim 1 or 6, wherein, The resin composition further contains an (F) curing accelerator.

24. The resin composition of claim 23, wherein, The (F) component contains at least one of an imidazole-based curing accelerator and a phosphorus-based curing accelerator.

25. The resin composition of claim 1 or 6, wherein, The resin composition further contains a (G) liquid thermosetting resin, wherein a resin corresponding to a maleimide resin is excluded.

26. The resin composition of claim 25, wherein, The (G) component contains a cyclic structure.

27. The resin composition of claim 25, wherein, The (G) component contains one or more functional groups selected from a vinyl group, an allyl group, a (meth)acryloyl group, and an amino group.

28. The resin composition of claim 25, wherein, The (G) component contains a benzoxazine resin.

29. The resin composition of claim 24, wherein, The content of the (G) component is 5% by mass or less, based on 100% by mass of the nonvolatile components in the resin composition.

30. The resin composition of claim 25, wherein, The content of the (G) component is 3% by mass or more and 15% by mass or less, based on 100% by mass of the resin components in the resin composition.

31. The resin composition of claim 25, wherein, The mass ratio of the (G) component to the (A-1) component, that is, (G) component / (A-1) component, is 0.01 or more and 2 or less.

32. The resin composition of claim 25, wherein, The mass ratio of the (G) component to the (A-2) component, that is, (G) component / (A-2) component, is 0.01 or more and 2 or less.

33. The resin composition of claim 25, wherein, The mass ratio of the (G) component to the (B) component, that is, (G) component / (B) component, is 0.01 or more and 2 or less.

34. The resin composition of claim 25, wherein, The mass ratio of the (G) component to the (D) component, that is, (G) component / (D) component, is 0.001 or more and 0.3 or less.

35. The resin composition of claim 1, wherein, The mass ratio of the (A-1) component to the (B) component, that is, (A-1) component / (B) component, is 0.1 or more and 5 or less.

36. The resin composition of claim 6, wherein, The mass ratio of the (A-2) component to the (B) component, that is, (A-2) component / (B) component, is 0.1 or more and 5 or less.

37. The resin composition of claim 1 or 6, wherein, The mass ratio of the (B) component to the (D) component, that is, (B) component / (D) component, is 0.05 or more and 1 or less.

38. The resin composition of claim 1, wherein, The mass ratio of the (C) component to the (A-1) component, that is, (C) component / (A-1) component, is 0.01 or more and 0.1 or less.

39. The resin composition of claim 6, wherein, The mass ratio of the (C) component to the (A-2) component, that is, (C) component / (A-2) component, is 0.01 or more and 0.1 or less.

40. The resin composition of claim 1 or 6, wherein, The mass ratio of the (C) component to the (B) component, that is, (C) component / (B) component, is 0.01 or more and 0.1 or less.

41. The resin composition of claim 1 or 6, wherein, The mass ratio of the (C) component to the (D) component, i.e., (C) component / (D) component, is 0.001 or more and 0.02 or less.

42. The resin composition of claim 25, wherein, The mass ratio of the (C) component to the (G) component, i.e., (C) component / (G) component, is 0.001 or more and 0.02 or less.

43. The resin composition of claim 1 or 6, which does not contain a fluororesin.

44. A resin sheet comprising: a support and a resin composition layer formed on the support, wherein The resin composition layer contains the resin composition of claim 1 or 6.

45. A circuit substrate comprising a cured product of the resin composition of claim 1 or 6.

46. A semiconductor device comprising the circuit substrate of claim 45.

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