Aromatic oxycarbonyl compound

Abstract

Provided is an aromatic oxycarbonyl compound which is useful as an epoxy resin curing agent and exhibits excellent solubility.　This aromatic oxycarbonyl compound is represented by formula (1). (In the formula, XAs each independently represent a monovalent organic group containing at least one aromatic ring (a), XBs each independently represent a divalent organic group containing at least one aromatic ring (b), XCs each independently represent a divalent organic group containing at least one aromatic ring (c), and n represents an integer of at least 1, where at least one XA is a monovalent organic group represented by formula (A-1), and at least one XC is a divalent organic group represented by formula (C-1).) (In the formula, Ar represents an aromatic group, RA1s each independently represent a monovalent organic group containing at least one aromatic ring, na1 represents an integer of 1-7, and * represents a bond.) (In the formula, ArC1 represents an aromatic group and * represents a bond.)

Description

Anomalous oxycarbonyl compounds

[0001] This invention relates to aromatic oxycarbonyl compounds. Furthermore, it relates to epoxy resin curing agents, resin compositions, resin sheets, prepregs, cured products, circuit boards, semiconductor chip packages, and semiconductor devices obtained using the aromatic oxycarbonyl compounds, as well as to methods for producing aromatic oxycarbonyl compounds.

[0002] Thermosetting resins such as epoxy resins and resin compositions containing their curing agents have been widely used as materials for electronic components such as circuit boards and semiconductor chip packages because they produce cured products with excellent insulation, heat resistance, and adhesion.

[0003] On the other hand, in high-speed communications such as fifth-generation mobile communication systems (5G), transmission loss when operating in a high-frequency environment becomes a problem. Therefore, insulating materials with excellent dielectric properties (low dielectric constant, low dielectric loss tangent) are required. In addition, the amount of heat generated by electronic components tends to increase when operating in a high-frequency environment, so insulating materials used for high-speed communications also require further improvements in heat resistance.

[0004] As an insulating resin material with excellent dielectric properties and heat resistance, for example, Patent Document 1 specifically discloses an active ester compound having a diphenylphosphinyl group and a naphthoxy group at its terminal end, used as a curing agent for epoxy resins. Furthermore, Patent Document 2 discloses an active ester compound having an HCA (9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide) structure.

[0005] Chinese Patent Application Publication No. 118047935, Specification International Publication No. 2018 / 103276

[0006] Here, it is conceivable to use an epoxy resin curing agent containing phosphorus to impart flame retardancy to the insulating material. However, the inventors have found that introducing phosphorus into the epoxy resin curing agent reduces its solubility, which may prevent the proper production of an insulating layer (cured product). In particular, the inventors have confirmed that the active ester compounds described in Patent Documents 1 and 2 have poor solubility in solvents and other resins, which may prevent the proper production of an insulating layer (cured product). Furthermore, the inventors have also confirmed that improving the epoxy resin curing agent to meet the dielectric properties and heat resistance required for high-speed communication such as fifth-generation mobile communication systems (5G) reduces the solubility of the epoxy resin curing agent, which may prevent the proper production of an insulating layer (cured product).

[0007] The present invention has been made in view of the above problems, and aims to provide an aromatic oxycarbonyl compound that exhibits excellent solubility and is useful as an epoxy resin curing agent.

[0008] As a result of diligent research by the present inventors, it was confirmed that the structure of the phosphorus substituent and the structure of the terminal portion are important for the solubility of phosphorus-containing aromatic oxycarbonyl compounds. Furthermore, it was found that the above problems can be solved by using an aromatic oxycarbonyl compound having the following structure, and thus the present invention was completed.

[0009] In other words, the present invention includes the following: [1] An aromatic oxycarbonyl compound represented by the following formula (1). (In the formula, X Ａ Each independently represents a monovalent organic group containing at least one aromatic ring (a), X Ｂ Each independently represents a divalent organic group containing at least one aromatic ring (b), X Ｃ Each independently represents a divalent organic group containing at least one aromatic ring (c), and n represents an integer of 1 or more. However, at least one X Ａ However, it is a monovalent organic group represented by the following formula (A-1), and at least one X Ｃ However, it is a divalent organic group represented by the following formula (C-1). (wherein Ar represents an aromatic group, R Ａ１ each independently represents a monovalent organic group containing at least one aromatic ring, na1 represents an integer of 1 to 7, and * represents a binding site.) (wherein Ar Ｃ１ represents an aromatic group, and * represents a binding site.) [2] The aromatic oxycarbonyl compound according to [1], wherein two X in formula (1) Ａ are each a monovalent organic group represented by formula (A-1) above. [3] The aromatic oxycarbonyl compound according to [1] or [2], wherein Ar in formula (A-1) is an aromatic hydrocarbon group. [4] The aromatic oxycarbonyl compound according to any one of [1] to [3], wherein Ar in formula (A-1) is an aromatic group having 6 to 14 carbon atoms. [5] The aromatic oxycarbonyl compound according to any one of [1] to [4], wherein R in formula (A-1) Ａ１ are each independently a monovalent organic group represented by the following formula (A-2). (wherein in formula (A-2), L Ａ１ represents a single bond or an alkylene group, ring Ar Ａ１ represents an aromatic ring which may have a substituent, and * represents a binding site.) [6] The aromatic oxycarbonyl compound according to [5], wherein L in formula (A-2) Ａ１ is a single bond. [7] The aromatic oxycarbonyl compound according to [5] or [6], wherein ring Ar in formula (A-2) Ａ１ is an aromatic carbocyclic ring which may have a substituent. [8] The aromatic oxycarbonyl compound according to any one of [5] to [7], wherein ring Ar in formula (A-2) Ａ１ is an aromatic ring having 6 to 14 carbon atoms which may have a substituent. [9] The aromatic oxycarbonyl compound according to any one of [1] to [8], wherein the aromatic ring (b) is an aromatic carbocyclic ring having 6 to 14 carbon atoms which may have one or more substituents selected from a halogen atom, an alkyl group, an aryl group and an arylalkyl group.

[10] The aromatic oxycarbonyl compound according to any one of [1] to [9], wherein Ar in formula (C-1) Ｃ１ is an aromatic hydrocarbon group.

[11] In formula (C-1), Ar Ｃ１However, an aromatic oxycarbonyl compound according to any of [1] to

[10] , wherein the aromatic group has 6 to 14 carbon atoms.

[12] An aromatic oxycarbonyl compound according to any of [1] to

[11] , wherein n is an integer between 1 and 6.

[13] An aromatic oxycarbonyl compound which is a condensate of a compound represented by the following formula (X-1), a compound represented by the following formula (X-2), and a divalent aromatic carboxylic acid halide compound or a divalent aromatic carboxylic acid compound. (In the formula, Ar represents an aromatic group, and R Ａ１ Each independently represents a monovalent organic group containing at least one aromatic ring, na1 represents an integer from 1 to 7, and Ar Ｃ１ (where represents an aromatic group.)

[14] A method for producing an aromatic oxycarbonyl compound, comprising the step of reacting a compound represented by the following formula (X-1), a compound represented by the following formula (X-2), and a divalent aromatic carboxylic acid halide compound or a divalent aromatic carboxylic acid compound. (In the formula, Ar represents an aromatic group, and R Ａ１ Each independently represents a monovalent organic group containing at least one aromatic ring, na1 represents an integer from 1 to 7, and Ar Ｃ１(wherein represents an aromatic group.)

[15] An epoxy resin curing agent comprising an aromatic oxycarbonyl compound according to any one of [1] to

[13] .

[16] A resin composition comprising (A) an aromatic oxycarbonyl compound according to any one of [1] to

[13] and (B) an epoxy resin.

[17] The resin composition according to

[16] , further comprising (C) a curing accelerator.

[18] The resin composition according to

[16] or

[17] , further comprising an epoxy resin curing agent other than component (A) (hereinafter referred to as "component (D)").

[19] The resin composition according to any one of

[16] to

[18] , further comprising (E) a thermoplastic resin.

[20] The resin composition according to any one of

[16] to

[19] , further comprising (F) an inorganic filler.

[21] The resin composition according to any one of

[16] to

[20] , further comprising (I) an organic solvent.

[22] The resin composition according to any one of

[16] to

[21] , for use as an insulating layer of a circuit board.

[23] A resin composition according to any one of

[16] to

[21] for semiconductor encapsulation.

[24] A resin sheet comprising a support and a layer of the resin composition according to any one of

[16] to

[23] provided on the support.

[25] The resin sheet according to

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

[26] A prepreg obtained by impregnating a sheet-like fibrous substrate with the resin composition according to any one of

[16] to

[23] .

[27] A cured product of the resin composition according to any one of

[16] to

[23] .

[28] A circuit board comprising an insulating layer having a cured product of the resin composition according to any one of

[16] to

[23] .

[29] A semiconductor chip package comprising a encapsulation layer having a cured product of the resin composition according to any one of

[16] to

[23] .

[30] The semiconductor chip package according to

[29] , which is a fan-out type package.

[31] A semiconductor device comprising the circuit board according to

[28] .

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

[29] or

[30] .

[0010] According to the present invention, it is possible to provide an aromatic oxycarbonyl compound exhibiting excellent solubility, an epoxy resin curing agent, a resin composition, a resin sheet, a prepreg, a cured product, a circuit board, a semiconductor chip package, and a semiconductor device obtained using the aromatic oxycarbonyl compound, and a method for producing the aromatic oxycarbonyl compound.

[0011] Figure 1 shows the GPC chart of aromatic oxycarbonyl compound (1) in Example 1. Figure 2 shows the IR chart of aromatic oxycarbonyl compound (1) in Example 1. Figure 3 shows the GPC chart of aromatic oxycarbonyl compound (2) in Example 2. Figure 4 shows the IR chart of aromatic oxycarbonyl compound (2) in Example 2. Figure 5 shows the GPC chart of aromatic oxycarbonyl compound (3) in Example 3. Figure 6 shows the IR chart of aromatic oxycarbonyl compound (3) in Example 3. Figure 7 shows the GPC chart of aromatic oxycarbonyl compound (4) in Example 4. Figure 8 shows the IR chart of aromatic oxycarbonyl compound (4) in Example 4. Figure 9 shows the GPC chart of aromatic oxycarbonyl compound (5) in Example 5. Figure 10 shows the IR chart of aromatic oxycarbonyl compound (5) in Example 5. Figure 11 shows the GPC chart of aromatic oxycarbonyl compound (6) in Example 6. Figure 12 shows the IR chart of aromatic oxycarbonyl compound (6) in Example 6. Figure 13 shows the GPC chart of aromatic oxycarbonyl compound (7) in Example 7. Figure 14 shows the IR chart of aromatic oxycarbonyl compound (7) in Example 7. Figure 15 shows the GPC chart of aromatic oxycarbonyl compound (C1) in Comparative Example 1. Figure 16 shows the IR chart of aromatic oxycarbonyl compound (C1) in Comparative Example 1. Figure 17 shows the GPC chart of aromatic oxycarbonyl compound (C2) in Comparative Example 2. Figure 18 shows the IR chart of aromatic oxycarbonyl compound (C2) in Comparative Example 2.

[0012] The present invention will be described in detail below with reference to embodiments and examples. However, the present invention is not limited to the embodiments and examples listed below, and may be implemented with modifications as appropriate without departing from the scope of the claims and their equivalents.

[0013] [Explanation of Terms] In the following explanation, the notations "XX or greater and YY or less" or "XX to YY" that represent a numerical range mean a numerical range that includes the lower and upper limits, unless otherwise specified. When a numerical range is described in steps, the upper and lower limits of each numerical range can be combined in any way.

[0014] In the following explanation, "non-volatile components" refers to components of the resin composition other than the organic solvents described later. Furthermore, "resin components" refers to components of the resin composition other than the inorganic fillers described later.

[0015] In the following explanation, unless otherwise specified, "dielectric constant" refers to "relative dielectric constant."

[0016] In the following descriptions, the phrase "may have substituents" when referring to a compound or group means, unless otherwise specified, both cases where the hydrogen atoms of the compound or group are not substituted by substituents, and cases where some or all of the hydrogen atoms of the compound or group are substituted by substituents. Furthermore, when describing the number of constituent atoms or carbon atoms of the compound or group, unless otherwise specified, the number of constituent atoms or carbon atoms of substituents is not included.

[0017] In this specification, unless otherwise specified, the term "substituent" means halogen atoms, alkyl groups, alkenyl groups, alkynyl groups, alcapopolyenyl groups, cycloalkyl groups, cycloalkenyl groups, alkoxy groups, cycloalkyloxy groups, aryl groups, aryloxy groups, arylalkyl groups, arylalkoxy groups, monovalent heterocyclic groups, alkylidene groups, amino groups, silyl groups, acyl groups, acyloxy groups, (meth)acryloyl groups, carboxyl groups, sulfo groups, cyano groups, nitro groups, hydroxyl groups, mercapto groups, and oxo groups. Groups containing only carbon and hydrogen, such as alkyl groups, alkenyl groups, alkynyl groups, alcapopolyenyl groups, cycloalkyl groups, cycloalkenyl groups, aryl groups, arylalkyl groups, and alkylidene groups, are collectively referred to as "hydrocarbon groups." Groups containing unsaturated bonds, such as alkenyl groups, alkynyl groups, alcapopolyenyl groups, cycloalkenyl groups, and (meth)acryloyl groups, are collectively referred to as "unsaturated bond-containing groups." Here, "(meth)acryloyl group" refers to both the acryloyl group and the methacryloyl group.

[0018] Examples of halogen atoms that can be used as substituents include fluorine, chlorine, bromine, and iodine atoms.

[0019] The alkyl group used as a substituent may be linear or branched. The number of carbon atoms in the alkyl group is preferably 1 to 20, more preferably 1 to 14, even more preferably 1 to 12, even more preferably 1 to 6, and particularly preferably 1 to 3. Examples of the alkyl group include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, and decyl groups.

[0020] The alkenyl group used as a substituent may be linear or branched. The number of carbon atoms in the alkenyl group is preferably 2 to 20, more preferably 2 to 14, even more preferably 2 to 12, even more preferably 2 to 6, and particularly preferably 2 or 3. Examples of the alkenyl group include vinyl, allyl, 1-propenyl, butenyl, sec-butenyl, isobutenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, and decenyl groups.

[0021] The alkynyl group used as a substituent may be linear or branched. The number of carbon atoms in the alkynyl group is preferably 2 to 20, more preferably 2 to 14, even more preferably 2 to 12, even more preferably 2 to 6, and particularly preferably 2 or 3. Examples of the alkynyl group include ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl, octinyl, noninyl, and desynyl groups.

[0022] The alkapolienyl group used as a substituent may be linear or branched, and the number of double bonds is preferably 2 to 10, more preferably 2 to 6, even more preferably 2 to 4, and even more preferably 2. The number of carbon atoms in the alkapolienyl group is preferably 3 to 20, more preferably 3 to 14, even more preferably 3 to 12, and even more preferably 3 to 6.

[0023] The number of carbon atoms in the cycloalkyl group used as a substituent is preferably 3 to 20, more preferably 3 to 12, and even more preferably 3 to 6. Examples of the cycloalkyl group include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl groups.

[0024] The number of carbon atoms in the cycloalkenyl group used as a substituent is preferably 3 to 20, more preferably 3 to 12, and even more preferably 3 to 6. Examples of the cycloalkenyl group include the cyclopropenyl group, cyclobutenyl group, cyclopentenyl group, and cyclohexenyl group.

[0025] The alkoxy group used as a substituent may be linear or branched. The number of carbon atoms in the alkoxy group is preferably 1 to 20, more preferably 1 to 12, and even more preferably 1 to 6. Examples of the alkoxy group include methoxy, ethoxy, propyloxy, isopropyloxy, butoxy, sec-butoxy, isobutoxy, tert-butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, and decyloxy groups.

[0026] The number of carbon atoms in the cycloalkyloxy group used as a substituent is preferably 3 to 20, more preferably 3 to 12, and even more preferably 3 to 6. Examples of the cycloalkyloxy group include the cyclopropyloxy group, the cyclobutyloxy group, the cyclopentyloxy group, and the cyclohexyloxy group.

[0027] The aryl group used as a substituent is a group obtained by removing one hydrogen atom from the aromatic ring of an aromatic hydrocarbon. The number of carbon atoms in the aryl group used as a substituent is preferably 6 to 24, more preferably 6 to 18, even more preferably 6 to 14, and even more preferably 6 to 10. Examples of the aryl group include the phenyl group, the naphthyl group, and the anthracenyl group.

[0028] The number of carbon atoms in the aryloxy group used as a substituent is preferably 6 to 24, more preferably 6 to 18, even more preferably 6 to 14, and even more preferably 6 to 10. Examples of aryloxy groups used as substituents include phenoxy, 1-naphthyloxy, and 2-naphthyloxy groups.

[0029] The number of carbon atoms in the arylalkyl group used as a substituent is preferably 7 to 25, more preferably 7 to 19, even more preferably 7 to 15, and even more preferably 7 to 11. Examples of the arylalkyl group include phenyl-C １ ~C １２ Alkyl, naphthyl-C １ ~C １２ Alkyl groups and anthracenyl-C１ ~C １２ Alkyl groups are examples.

[0030] The number of carbon atoms in the arylalkoxy group used as a substituent is preferably 7 to 25, more preferably 7 to 19, even more preferably 7 to 15, and even more preferably 7 to 11. Examples of the arylalkoxy group include phenyl-C １ ~C １２ Alkoxy group, and naphthyl-C １ ~C １２ An example is an alkoxy group.

[0031] A monovalent heterocyclic group used as a substituent refers to a group obtained by removing one hydrogen atom from the heterocycle of a heterocyclic compound. The number of carbon atoms in the monovalent heterocyclic group is preferably 3 to 21, more preferably 3 to 15, and even more preferably 3 to 9. The monovalent heterocyclic group also includes a monovalent aromatic heterocyclic group (heteroaryl group). Examples of the monovalent heterocycle include the thienyl group, pyrrolyl group, furanyl group, furyl group, pyridyl group, pyridadinyl group, pyrimidyl group, pyrazinyl group, triazinyl group, pyrrolidyl group, piperidyl group, quinolyl group, and isoquinolyl group.

[0032] An alkylidene group used as a substituent is a group obtained by removing two hydrogen atoms from the same carbon atom of an alkane. The number of carbon atoms in the alkylidene group is preferably 1 to 20, more preferably 1 to 14, even more preferably 1 to 12, even more preferably 1 to 6, and particularly preferably 1 to 3. Examples of the alkylidene group include methylidene, ethylidene, propyridene, isopropylidene, butylidene, sec-butylidene, isobutylidene, pentylidene, hexylidene, heptylidene, octylidene, nonylidene, and desylidene.

[0033] The acyl group used as a substituent is a group represented by the formula: -C(=O)-R (wherein R is an alkyl group or an aryl group). The alkyl group represented by R may be linear or branched. Examples of the aryl group represented by R include the phenyl group, naphthyl group, and anthracenyl group. The number of carbon atoms in the acyl group is preferably 2 to 20, more preferably 2 to 13, and even more preferably 2 to 7. Examples of the acyl group include the acetyl group, propionyl group, butyryl group, isobutyryl group, pivaloyl group, and benzoyl group.

[0034] The acyloxy group used as a substituent is a group represented by the formula: -O-C(=O)-R (wherein R is an alkyl group or an aryl group). The alkyl group represented by R may be linear or branched. Examples of the aryl group represented by R include the phenyl group, the naphthyl group, and the anthracenyl group. The number of carbon atoms in the acyloxy group is preferably 2 to 20, more preferably 2 to 13, and even more preferably 2 to 7. Examples of the acyloxy group include the acetoxy group, the propionyloxy group, the butyryloxy group, the isobutyryloxy group, the pivaloyloxy group, and the benzoyloxy group.

[0035] The substituents described above may have further substituents (hereinafter sometimes referred to as "secondary substituents"). Unless otherwise specified, the same substituents described above may be used as secondary substituents.

[0036] In the following description, the term "organic group" refers to a group that includes at least one carbon atom as a skeletal atom, and may be linear, branched, or cyclic. In this specification, unless otherwise specified, the number of skeletal atoms in an organic group is preferably 1 to 3000, more preferably 1 to 1000, even more preferably 1 to 100, even more preferably 1 to 50, and particularly preferably 1 to 30 or 1 to 20. Examples of organic groups include groups consisting of one or more skeletal atoms selected from carbon atoms, oxygen atoms, nitrogen atoms, and sulfur atoms (provided that at least one carbon atom is included).

[0037] In this specification, the term "hydrocarbon group" refers to a group obtained by removing one or more hydrogen atoms from a hydrocarbon compound. More specifically, a monovalent hydrocarbon group refers to a group obtained by removing one hydrogen atom from a hydrocarbon compound, and a divalent hydrocarbon group refers to a group obtained by removing two hydrogen atoms from a hydrocarbon compound. Examples of hydrocarbon groups include aliphatic groups and aromatic groups, which will be described later, and which contain only carbon atoms and hydrogen atoms. In this specification, an aliphatic group containing only carbon atoms and hydrogen atoms is also called an "aliphatic hydrocarbon group," and an aromatic group containing only carbon atoms and hydrogen atoms is also called an "aromatic hydrocarbon group."

[0038] In this specification, the term "aliphatic group" refers to a group from which one or more hydrogen atoms bonded to an aliphatic carbon of an aliphatic compound have been removed. More specifically, a monovalent aliphatic group refers to a group from which one hydrogen atom bonded to an aliphatic carbon of an aliphatic compound has been removed, and a divalent aliphatic group refers to a group from which two hydrogen atoms bonded to an aliphatic carbon of an aliphatic compound have been removed. Examples of divalent aliphatic groups include optionally substituted alkylene groups, optionally substituted cycloalkylene groups, optionally substituted alkenylene groups, optionally substituted cycloalkenylene groups, and optionally substituted alkapolienylene groups (preferably 2 to 10, more preferably 2 to 6, even more preferably 2 to 4, and even more preferably 2 double bonds). In this specification, unless otherwise specified, the number of carbon atoms in an 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. The number of carbon atoms in substituents is not included in this number of carbon atoms.

[0039] In the following description, "aromatic ring" refers to a ring that obeys Hückel's rule, where the number of electrons in the π-electron system on the ring is 4r + 2 (where r is a natural number), and includes monocyclic aromatic rings and fused polycyclic aromatic rings formed by the fusion of two or more monocyclic aromatic rings. Monocyclic aromatic rings are preferred as aromatic rings. Aromatic rings can be aromatic carbocyclic rings having only carbon atoms as ring constituent atoms, or aromatic heterocyclic rings having heteroatoms such as oxygen, nitrogen, or sulfur atoms in addition to carbon atoms as ring constituent atoms. Aromatic carbocyclic rings are preferred as aromatic rings. The number of carbon atoms in an aromatic ring is preferably 3 or more, more preferably 4 or more or 5 or more, and even more preferably 6 or more, with an upper limit preferably 24 or less, more preferably 18 or less or 14 or less, and even more preferably 10 or less. The number of carbon atoms of substituents is not included in the number of carbon atoms.

[0040] Examples of monocyclic aromatic rings include benzene rings, furan rings, thiophene rings, pyrrole rings, pyrazole rings, oxazole rings, isoxazole rings, furazan rings, thiazole rings, isothiazole rings, thiadiazole rings, imidazole rings, triazole rings, tetrazole rings, pyridine rings, pyridazine rings, pyrimidine rings, pyrazine rings, and pyridazine rings. Examples of condensed polycyclic aromatic rings formed by the condensation of two or more monocyclic aromatic rings include naphthalene rings, anthracene rings, phenanthrene rings, benzofuran rings, isobenzofuran rings, indole rings, isoindole rings, benzothiophene rings, benzimidazole rings, indazole rings, benzoxazole rings, benzoisoxazole rings, benzothiazole rings, quinoline rings, isoquinoline rings, quinoxaline rings, acridine rings, quinazoline rings, sinnoline rings, phthalazine rings, pyridothiazole rings, benzotriazole rings, imidazopyridine rings, triazopyridine rings, and purine rings. Benzene rings or naphthalene rings are preferred as the aromatic rings, with benzene rings being more preferred.

[0041] In this specification, the term "aromatic group" means a group obtained by removing one or more hydrogen atoms from the aromatic ring of an aromatic compound. More specifically, a monovalent aromatic group means a group obtained by removing one hydrogen atom from the aromatic ring of an aromatic compound, and a divalent aromatic group means a group obtained by removing two hydrogen atoms from the aromatic ring of an aromatic compound. Examples of monovalent aromatic groups include optionally substituted aryl groups and optionally substituted heteroaryl groups, and examples of divalent aromatic groups include optionally substituted arylene groups and optionally substituted heteroarylene groups. In this specification, unless otherwise specified, the number of carbon atoms in an aromatic group is preferably 3 or more, more preferably 4 or more or 5 or more, and even more preferably 6 or more, with an upper limit preferably 24 or less, more preferably 18 or less or 14 or less, and even more preferably 10 or less. The number of carbon atoms does not include the number of carbon atoms of substituents.

[0042] In the following description, the "aromatic oxycarbonyl compound according to the first embodiment" and the "aromatic oxycarbonyl compound according to the second embodiment" may be collectively referred to as the "aromatic oxycarbonyl compound."

[0043] [Aromatic oxycarbonyl compound according to the first embodiment] The aromatic oxycarbonyl compound according to the first embodiment of the present invention is an aromatic oxycarbonyl compound represented by the following formula (1). (In the formula, X Ａ Each independently represents a monovalent organic group containing at least one aromatic ring (a), X Ｂ Each independently represents a divalent organic group containing at least one aromatic ring (b), X Ｃ Each independently represents a divalent organic group containing at least one aromatic ring (c), and n represents an integer of 1 or more. However, at least one X Ａ However, it is a monovalent organic group represented by the following formula (A-1), and at least one X Ｃ However, it is a divalent organic group represented by the following formula (C-1). (In the formula, Ar represents an aromatic group, and R Ａ１Each of these independently represents a monovalent organic group containing at least one aromatic ring, na1 represents an integer from 1 to 7, and * represents a bond. (In the formula, Ar Ｃ１ (where * represents an aromatic group, and * represents a bond.)

[0044] The aromatic oxycarbonyl compound according to the first embodiment of the present invention has a terminal group X Ａ At least one of the components is a monovalent organic group represented by the above formula (A-1), which improves solubility in organic solvents and other resins. Furthermore, the aromatic oxycarbonyl compound according to the first embodiment of the present invention is X Ｃ At least one of the components is a divalent organic group represented by the above formula (C-1) containing phosphorus, which can result in a cured product exhibiting excellent flame retardancy. Furthermore, the aromatic oxycarbonyl compound according to the first embodiment of the present invention, by having multiple ester bonds as shown in formula (1), can produce a cured product exhibiting excellent dielectric properties and excellent heat resistance when combined with an epoxy resin. Conventional epoxy resin curing agents containing phosphorus have found it difficult to simultaneously achieve all four: excellent flame retardancy, excellent dielectric properties, excellent heat resistance, and excellent solubility. However, the aromatic oxycarbonyl compound according to the first embodiment of the present invention can produce a cured product exhibiting excellent solubility while also exhibiting excellent flame retardancy, excellent dielectric properties, and excellent heat resistance.

[0045] An aromatic oxycarbonyl compound according to the first embodiment of the present invention is an aromatic oxycarbonyl compound represented by formula (1), and X Ａ , X Ｂ , X Ｃ Alternatively, it may be a mixture of two or more aromatic oxycarbonyl compounds with different values ​​of n.

[0046] <Monovalent organic group X Ａ > In formula (1), X Ａ Each independently represents a monovalent organic group containing at least one aromatic ring (a), and at least one X Ａ This is a monovalent organic group represented by the above formula (A-1). The two X in formula (1) ＡThese may be the same or different from each other, but it is preferable that they be the same. In one embodiment, in formula (1), the two X Ａ However, it is preferable that it be a monovalent organic group represented by the above formula (A-1).

[0047] X Ａ The aromatic ring (a) contained in may be either a monocyclic aromatic ring or a condensed polycyclic aromatic ring formed by the condensation of two or more monocyclic aromatic rings, as described above in the [Explanation of Terms] section. Also, X Ａ The aromatic ring (a) contained therein may be either an aromatic carbocyclic ring or an aromatic heterocyclic ring.

[0048] In combination with epoxy resin, X is used to produce a cured product that exhibits even better dielectric properties and heat resistance. Ａ The aromatic ring (a) contained in is preferably an aromatic carbon ring. The aromatic carbon ring may be either a monocyclic aromatic carbon ring or a fused polycyclic aromatic carbon ring, and its number of carbon atoms is preferably 6 to 14, more preferably 6 to 10. Therefore, in one preferred embodiment, X Ａ The aromatic ring (a) contained in it is an aromatic carbon ring having 6 to 14 carbon atoms.

[0049] In combination with epoxy resin, X is used to produce a cured product that exhibits even better dielectric properties and heat resistance. Ａ The number of aromatic rings (a) contained in is X Ａ Preferably, there are one or more per unit, more preferably two or more. The upper limit is preferably 10 or less, 8 or less, or 5 or less, more preferably 4 or less, and even more preferably 3 or less. In one embodiment, X Ａ The number of aromatic rings (a) contained in is X Ａ Preferably, there are 1 to 5 pieces per unit, more preferably 1 to 3 pieces, even more preferably 1 or 2 pieces, and particularly preferably 2 pieces.

[0050] X ＡThe aromatic ring (a) contained therein may have substituents. Such substituents are as described above in the [Explanation of Terms] section, but among them, from the viewpoint of obtaining a cured product that exhibits even better dielectric properties and heat resistance when combined with epoxy resin, one or more selected from halogen atoms, hydrocarbon groups and alkoxy groups is preferred, one or more selected from halogen atoms, alkyl groups, aryl groups and arylalkyl groups is more preferred, and one or more selected from fluorine atoms, alkyl groups having 1 to 6 carbon atoms, aryl groups having 6 to 10 carbon atoms and arylalkyl groups having 7 to 12 carbon atoms is even more preferred.

[0051] Therefore, in a preferred embodiment, X Ａ The aromatic ring (a) contained therein is an aromatic carbon ring having 6 to 14 carbon atoms, which may have one or more substituents selected from halogen atoms, alkyl groups, aryl groups, and arylalkyl groups.

[0052] X Ａ This is a monovalent organic group, that is, a group containing at least one carbon atom as a skeletal atom, but preferably a monovalent group consisting of one or more (preferably 1 to 100, 1 to 50, or 1 to 30) skeletal atoms selected from carbon, oxygen, nitrogen, and sulfur atoms. In particular, from the viewpoint of obtaining a cured product that exhibits even better dielectric properties and heat resistance when combined with epoxy resin, X Ａ It is particularly preferable that the skeletal atoms consist only of carbon atoms or only of carbon atoms and oxygen atoms. Furthermore, the preferred range for the number of skeletal atoms is as described above, but among these, 6 to 30 or 10 to 30 is preferred.

[0053] In combination with epoxy resin, from the viewpoint of obtaining a cured product that exhibits both good dielectric properties and good heat resistance, in the above formula (1), X Ａ The oxygen atom bonded to it is X Ａ It is preferable that it is bonded to the aromatic carbon, that is, the carbon atom constituting the aromatic ring (a) described above.

[0054] X ＡThe number of carbon atoms is preferably 5 or more, more preferably 6 or more, even more preferably 7 or more, and particularly preferably 8 or more. In one embodiment, it may be 9 or more, 10 or more, 11 or more, etc. Ａ The upper limit of the number of carbon atoms is preferably 50 or less, more preferably 45 or less, even more preferably 40 or less or 35 or less, and particularly preferably 30 or less or 25 or less. In one embodiment, it may also be 22 or less, 20 or less, 18 or less, 15 or less, etc.

[0055] X Ａ The molecular weight is preferably 80 or higher, more preferably 90 or higher, even more preferably 100 or higher, and particularly preferably 110 or higher. In one embodiment, it may be 120 or higher, 130 or higher, 140 or higher, 150 or higher, etc. Ａ The upper limit of the molecular weight is preferably 600 or less, more preferably 500 or less, even more preferably 400 or less, and particularly preferably 300 or less. In one embodiment, it may be 250 or less, 200 or less, etc.

[0056] As mentioned above, in equation (1), at least one X Ａ However, it is a monovalent organic group represented by the above formula (A-1), and two X Ａ However, it is preferable that it be a monovalent organic group represented by the above formula (A-1).

[0057] In formula (A-1), na1 represents an integer from 1 to 7. na1 is preferably 6 or less, more preferably 5 or less, even more preferably 4 or less, and particularly preferably 3 or less or 2 or less. In one embodiment, na1 may also be 1.

[0058] In formula (A-1), Ar represents an aromatic group. Ar is an na1+1 valent aromatic group. Ar may be an aromatic hydrocarbon group or an aromatic heterocyclic group, but it is preferably an aromatic hydrocarbon group. The number of carbon atoms in Ar is preferably 6 to 14, and more preferably 6 to 10. That is, in one embodiment, Ar is preferably an aromatic hydrocarbon group having 6 to 14 carbon atoms. Specific examples of Ar include an na1+1 valent group obtained by removing na1+1 hydrogen atoms from benzene, and an na1+1 valent group obtained by removing na1+1 hydrogen atoms from naphthalene.

[0059] In formula (A-1), R Ａ１ Each of these independently represents a monovalent organic group containing at least one aromatic ring.

[0060] R Ａ１ The aromatic ring contained in is the aforementioned X Ａ It is similar to the aromatic ring (a) contained in R. Ａ１ The aromatic ring contained is preferably an aromatic carbon ring having 6 to 14 carbon atoms. In one embodiment, R Ａ１ It is preferable that it is an aromatic carbon ring having 6 to 14 carbon atoms.

[0061] In one embodiment, in formula (A-1), R Ａ１ Each of these is preferably a monovalent organic group represented by the following formula (A-2). (In formula (A-2), L Ａ１ represents a single bond or an alkylene group, and ring Ar Ａ１ (where * represents an aromatic ring that may have substituents, and * represents a bond.)

[0062] In formula (A-2), L Ａ１ L represents a single bond or an alkylene group, with a single bond being preferred. Ａ１ Because it is a single bond, when combined with epoxy resin, it can produce a cured product that exhibits better heat resistance. Ａ１ The number of carbon atoms in the alkylene group is preferably 1 to 10, more preferably 1 to 5, even more preferably 1 to 3, and particularly preferably 1 or 2. Ａ１Examples of alkylene groups in L include methylene, ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene, decylene, undecylene, dodecylene, ethylidene, 1,1-propyridene, and 2,2-propyridene (dimethylmethylene). Among these, L Ａ１ As such, a single bond, a methylene group, or an ethylidene group is preferred.

[0063] In formula (A-2), ring Ar Ａ１ This represents an aromatic ring which may have substituents. Ring Ar Ａ１ This may be an aromatic carbon ring or an aromatic heterocycle having substituents, with an aromatic carbon ring having substituents being preferred. Ａ１ The number of carbon atoms in the aromatic ring is preferably 6 to 14, and more preferably 6 to 10. That is, in one embodiment, the ring Ar Ａ１ It is preferably an aromatic carbon ring having 6 to 14 carbon atoms. Ａ１ Specific examples include benzene rings and naphthalene rings.

[0064] Ring Ar Ａ１ It may have substituents. Such substituents are as described above in the [Explanation of Terms] section, but among them, from the viewpoint of obtaining a cured product that exhibits even better dielectric properties and heat resistance in combination with epoxy resin, one or more selected from halogen atoms, hydrocarbon groups and alkoxy groups is preferred, one or more selected from halogen atoms, alkyl groups, aryl groups and arylalkyl groups is more preferred, and one or more selected from fluorine atoms, alkyl groups having 1 to 6 carbon atoms, aryl groups having 6 to 10 carbon atoms and arylalkyl groups having 7 to 12 carbon atoms is even more preferred. In one embodiment, ring Ar Ａ１ It is preferable that it does not have substituents.

[0065] Monovalent organic group X ＡSpecific examples thereof include a 2-phenylphenyl group, a 4-phenylphenyl group, groups represented by the following formulas (A-1-1) to (A-1-4), and the like. Note that m in formulas (A-1-1) to (A-1-4) corresponds to na1 in formula (A-1). (In the formula, m represents an integer of 1 to 3, and * represents a bonding hand.)

[0066] <Divalent organic group X Ｂ > In formula (1), X Ｂ each independently represents a divalent organic group containing at least one aromatic ring (b). In formula (1), n+1 X Ｂ groups may be the same or different from each other, and are preferably the same as each other.

[0067] X Ｂ The aromatic ring (b) contained in the divalent organic group represented by may be either a monocyclic aromatic ring or a fused polycyclic aromatic ring, as described above in the [Description of Terms] section. Further, the aromatic ring may be either an aromatic carbocyclic ring or an aromatic heterocyclic ring.

[0068] From the viewpoint of obtaining a cured product that exhibits both further improved dielectric properties and heat resistance when combined with an epoxy resin, the aromatic ring (b) is preferably an aromatic carbocyclic ring. The aromatic carbocyclic ring may be either a monocyclic aromatic carbocyclic ring or a fused polycyclic aromatic carbocyclic ring, and the number of carbon atoms thereof is preferably 6 to 14, more preferably 6 to 10. Therefore, in a preferred embodiment, X Ｂ The aromatic ring (b) contained in the divalent organic group represented by is an aromatic carbocyclic ring having 6 to 14 carbon atoms.

[0069] From the viewpoint of obtaining a cured product that exhibits both further improved dielectric properties and heat resistance when combined with an epoxy resin, X Ｂ The number of aromatic rings (b) contained in the divalent organic group represented by per X Ｂ group is preferably 1 to 3, more preferably 1 or 2. The number of aromatic rings as a substituent is not included in the number of the aromatic rings (b).

[0070] The aromatic ring (b) may have a substituent. Such substituents are as described above in the [Description of Terms] section. Among them, from the viewpoint of obtaining a cured product that exhibits both better dielectric properties and heat resistance when combined with an epoxy resin, one or more selected from a halogen atom, a hydrocarbon group and an alkoxy group is preferable; one or more selected from a halogen atom, an alkyl group, an aryl group and an arylalkyl group is more preferable; and one or more selected from a fluorine atom, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 10 carbon atoms, and an arylalkyl group having 7 to 12 carbon atoms is even more preferable. In one embodiment, the aromatic ring (b) may have no substituent.

[0071] Therefore, in a preferred embodiment, X Ｂ The aromatic ring (b) contained in the divalent organic group represented by is an aromatic carbocyclic ring having 6 to 14 carbon atoms which may have one or more substituents selected from a halogen atom, an alkyl group, an aryl group and an arylalkyl group.

[0072] X Ｂ The divalent organic group represented by is not particularly limited as long as it contains at least one of the above aromatic rings (b). As described above, it is a group containing at least a carbon atom as a skeleton atom, and preferably a divalent group consisting of 1 or more (preferably 1 to 100, 1 to 50, 1 to 30) skeleton atoms selected from a carbon atom, an oxygen atom, a nitrogen atom, and a sulfur atom. Among others, from the viewpoint of obtaining a cured product that exhibits both better dielectric properties and heat resistance when combined with an epoxy resin, X Ｂ It is particularly preferable that the divalent organic group represented by contains only carbon atoms or only carbon atoms and oxygen atoms as skeleton atoms. Further, the preferred range of the number of skeleton atoms is as described above, and among others, it is preferably 6 to 30 or 6 to 20.

[0073] From the viewpoint of obtaining a cured product that exhibits both good dielectric properties and good heat resistance when combined with an epoxy resin, in formula (1), X Ｂ the two carbonyl groups bonded to are X ＢIt is preferable that it is bonded to the aromatic carbon, that is, the carbon atom constituting the aromatic ring (b) described above.

[0074] In a preferred embodiment, X Ｂ (i) is a divalent group obtained by removing two hydrogen atoms from a monocyclic aromatic carbon ring which may have substituents, or (ii) is a divalent group obtained by removing two hydrogen atoms from a fused polycyclic aromatic carbon ring which may have substituents. In such embodiments, the monocyclic aromatic carbon ring or the fused polycyclic aromatic carbon ring is X Ｂ This corresponds to the "aromatic ring (b)" mentioned earlier. Ｂ When is the divalent group described in (i) above, X Ｂ X is a divalent organic group containing a single monocyclic aromatic carbocyclic ring. Ｂ When is the divalent group in (ii) above, X Ｂ is a divalent organic group containing one fused polycyclic aromatic carbocycle. Preferred examples of substituents that a monocyclic aromatic carbocycle or a fused polycyclic aromatic carbocycle may have are X Ｂ As explained regarding the "aromatic ring (b)" in the above, one or more selected from halogen atoms, alkyl groups, aryl groups, and arylalkyl groups are more preferred, and one or more selected from fluorine atoms, alkyl groups having 1 to 6 carbon atoms, aryl groups having 6 to 10 carbon atoms, and arylalkyl groups having 7 to 12 carbon atoms are even more preferred.

[0075] In particular, when combined with epoxy resin, X is used to produce a cured product that exhibits even better dielectric properties and heat resistance. Ｂ The divalent organic group represented by is preferably the divalent group of (i) above, and more preferably a divalent group obtained by removing two hydrogen atoms from an unsubstituted monocyclic aromatic carbocyclic ring.

[0076] X Ｂ Specific examples include phenylene groups and naphthylene groups.

[0077] <Divalent organic group X Ｃ > In formula (1), X ＣEach independently represents a divalent organic group containing at least one aromatic ring (c), and at least one X Ｃ However, it is a divalent organic group represented by the above formula (C-1). In formula (1), n ​​X Ｃ These may be the same or different from each other. In one embodiment, in formula (1), n ​​X Ｃ Preferably, all of them are divalent organic groups represented by the above formula (C-1).

[0078] X Ｃ The aromatic ring (c) contained in the divalent organic group represented by may be either a monocyclic aromatic ring or a fused polycyclic aromatic ring, as described above in the [Explanation of Terms] section. Furthermore, the aromatic ring may be either an aromatic carbocyclic ring or an aromatic heterocyclic ring.

[0079] In combination with epoxy resin, the aromatic ring (c) is preferably an aromatic carbon ring, from the viewpoint of obtaining a cured product that exhibits even better dielectric properties and heat resistance. The aromatic carbon ring may be either a monocyclic aromatic carbon ring or a fused polycyclic aromatic carbon ring, and its number of carbon atoms is preferably 6 to 14, more preferably 6 to 10. Therefore, in one preferred embodiment, X Ｃ The aromatic ring (c) contained in the divalent organic group represented by is an aromatic carbon ring having 6 to 14 carbon atoms.

[0080] In combination with epoxy resin, X is used to produce a cured product that exhibits even better dielectric properties and heat resistance. Ｃ The number of aromatic rings (c) in the divalent organic group represented by is X Ｃ Preferably, there are 1 to 3, more preferably 1 or 2, aromatic rings per unit. The number of aromatic rings (c) does not include the number of aromatic rings acting as substituents.

[0081] The aromatic ring (c) may have substituents. Such substituents can be those described above in the [Explanation of Terms] section. Furthermore, in combination with epoxy resin, from the viewpoint of obtaining a cured product that exhibits even better dielectric properties and heat resistance, one or more selected from diarylphosphinyl groups, halogen atoms, hydrocarbon groups and alkoxy groups is preferred, one or more selected from diphenylphosphinyl groups, halogen atoms, alkyl groups, aryl groups and arylalkyl groups is more preferred, and one or more selected from diphenylphosphinyl groups, fluorine atoms, alkyl groups having 1 to 6 carbon atoms, aryl groups having 6 to 10 carbon atoms and arylalkyl groups having 7 to 12 carbon atoms is even more preferred.

[0082] Therefore, in a preferred embodiment, X Ｃ The aromatic ring (c) contained in the divalent organic group represented by is an aromatic carbon ring having 6 to 14 carbon atoms, which may have one or more substituents selected from a diphenylphosphinyl group, a halogen atom, an alkyl group, an aryl group, and an arylalkyl group.

[0083] X Ｃ The divalent organic group represented by is not particularly limited as long as it contains at least one aromatic ring (c) as described above, and as mentioned above, it is a group that contains at least one carbon atom as a skeletal atom, but preferably a divalent group consisting of one or more (preferably 1 to 100, 1 to 50, or 1 to 30) skeletal atoms selected from carbon, oxygen, nitrogen, and sulfur atoms. In particular, from the viewpoint of obtaining a cured product that exhibits even better dielectric properties and heat resistance when combined with epoxy resin, X Ｃ The divalent organic group represented by is particularly preferably composed of only carbon atoms or only carbon and oxygen atoms as its skeletal atoms. Furthermore, while the preferred range for the number of skeletal atoms is as described above, it is especially preferable that it be 6 to 30 or 6 to 20.

[0084] In combination with epoxy resin, from the viewpoint of obtaining a cured product that exhibits both good dielectric properties and good heat resistance, in formula (1), X Ｃ The two oxygen atoms bonded to it are X ＣIt is preferable that it is bonded to the aromatic carbon, that is, the carbon atom constituting the aromatic ring (c) described above.

[0085] As mentioned above, in equation (1), at least one X Ｃ However, it is a divalent organic group represented by the above formula (C-1), and n X Ｃ Preferably, all of them are divalent organic groups represented by the above formula (C-1).

[0086] In formula (C-1), Ar Ｃ１ Ar represents an aromatic group. Ｃ１ Ar is a trivalent aromatic group. Ｃ１ This may be an aromatic hydrocarbon group or an aromatic heterocyclic group, but it is preferably an aromatic hydrocarbon group. Ｃ１ The number of carbon atoms is preferably 6 to 14, and more preferably 6 to 10. That is, in one embodiment, Ar Ｃ１ It is preferably an aromatic hydrocarbon group having 6 to 14 carbon atoms. Ｃ１ Specific examples include a trivalent group obtained by removing three hydrogen atoms from benzene, and a trivalent group obtained by removing three hydrogen atoms from naphthalene.

[0087] divalent organic group X Ｃ Specific examples include the group represented by the following formula (C-1-1) and the group represented by the following formula (C-1-2). (In the formula, * represents a bond.)

[0088] <Number of repetitions n> In formula (1), n ​​represents an integer of 1 or more. Preferably, n is 20 or less or 15 or less, more preferably 12 or less or 10 or less, even more preferably 8 or less or 7 or less, and particularly preferably 6 or less, 5 or less or 4 or less. In one embodiment, it is preferable that n is an integer between 1 and 6.

[0089] When the aromatic oxycarbonyl compound according to the first embodiment of the present invention is a mixture of aromatic oxycarbonyl compound lipids represented by the above formula (1) with different values ​​of n, the average value of n is preferably 1 to 20. The upper limit of the average value of n is more preferably 15 or less, 12 or less, or 10 or less, even more preferably 8 or less, or 7 or less, and particularly preferably 6 or less, 5 or less, or 4 or less.

[0090] <Specific Examples of Aromatic Oxycarbonyl Compounds> Specific examples of the aromatic oxycarbonyl compounds of the present invention represented by formula (1) include the compounds represented by the following formulas (1a), (4a), (5a), (6a), (7a), (7a-2), and (8a). (In the formula, m represents an integer between 1 and 3.)

[0091] [Aromatic oxycarbonyl compound according to the second embodiment of the present invention] The aromatic oxycarbonyl compound according to the second embodiment of the present invention is a condensate of a compound represented by the following formula (X-1), a compound represented by the following formula (X-2), and a divalent aromatic carboxylic acid halide compound or a divalent aromatic carboxylic acid compound. (In the formula, Ar represents an aromatic group, and R Ａ１ Each independently represents a monovalent organic group containing at least one aromatic ring, na1 represents an integer from 1 to 7, and Ar Ｃ１ (This represents an aromatic group.)

[0092] The aromatic oxycarbonyl compound according to the second embodiment of the present invention has a structure derived from the compound represented by formula (X-1) above, thereby improving its solubility in organic solvents and other resins. Furthermore, the aromatic oxycarbonyl compound according to the second embodiment of the present invention has a structure derived from the compound represented by formula (X-2) above, which contains phosphorus, thereby providing a cured product exhibiting excellent flame retardancy. Moreover, since the aromatic oxycarbonyl compound according to the second embodiment of the present invention is a condensate of the compound represented by formula (X-1), the compound represented by formula (X-2), and a divalent aromatic carboxylic acid halide compound or a divalent aromatic carboxylic acid compound, it has multiple ester bonds, and in combination with epoxy resins, it can provide a cured product exhibiting excellent dielectric properties and excellent heat resistance. Conventional epoxy resin curing agents containing phosphorus have found it difficult to simultaneously achieve excellent flame retardancy, excellent dielectric properties, excellent heat resistance, and excellent solubility. However, the aromatic oxycarbonyl compound according to the second embodiment of the present invention can provide a cured product that exhibits excellent solubility while also exhibiting excellent flame retardancy, excellent dielectric properties, and excellent heat resistance.

[0093] The aromatic oxycarbonyl compound according to the second embodiment of the present invention may be two or more compounds represented by formula (X-1), two or more compounds represented by formula (X-2), two or more divalent aromatic carboxylic acid halide compounds, or condensates of divalent aromatic carboxylic acid compounds.

[0094] <Aromatic group Ar> In formula (X-1), Ar represents an aromatic group and is the same as Ar in formula (A-1).

[0095] <Monovalent organic group R Ａ１ > In formula (X-1), R Ａ１ Each of these independently represents a monovalent organic group containing at least one aromatic ring, and R in formula (A-1) Ａ１ It is the same as this.

[0096] <Number of substitutions na1> In equation (X-1), na1 represents an integer from 1 to 7, and is the same as na1 in equation (A-1).

[0097] <Specific examples of compounds represented by formula (X-1)> Specific examples of compounds represented by formula (X-1) include 2-phenylphenol, 4-phenylphenol, and compounds represented by the following formulas (X-1-1) to (X-1-4). In formulas (X-1-1) to (X-1-4), m corresponds to na1 in formula (X-1). (In the formula, m represents an integer between 1 and 3.)

[0098] Examples of commercially available compounds represented by formula (X-1) include styrene-phenol "SP-F" (manufactured by Sankosha, the compound represented by formula (X-1-1) above). "SP-F" is a mixture in which the compound with m=1 in formula (X-1-1) is 75.3%, the compound with m=2 is 23.3%, and the compound with m=3 is 0.6%. That is, when "SP-F" is used as the compound represented by formula (X-1), aromatic oxycarbonyl compounds with na1 of 1 to 3 in formula (A-1) can be obtained.

[0099] <Aromatic group Ar Ｃ１ > In formula (X-2), Ar Ｃ１ represents an aromatic group, and in formula (C-1) Ar Ｃ１ It is the same as this.

[0100] <Specific examples of compounds represented by formula (X-2)> Specific examples of compounds represented by formula (X-2) include the compound represented by the following formula (X-2-1) and the compound represented by the following formula (X-2-2).

[0101] <Divalent Aromatic Carboxylic Acid Halide Compound or Divalent Aromatic Carboxylic Acid Compound> The divalent aromatic carboxylic acid halide compound or divalent aromatic carboxylic acid compound relating to the aromatic oxycarbonyl compound of the second embodiment of the present invention is preferably a compound represented by the following formula (X-3). (In formula (X-3), X Ｂ (where (b) represents a divalent organic group containing at least one aromatic ring, and Y represents a halogen atom or a hydroxyl group.)

[0102] In formula (X-3), X ＢX represents a divalent organic group containing at least one aromatic ring (b), and X in formula (1) Ｂ It is the same as this.

[0103] In formula (X-3), Y represents a halogen atom or a hydroxyl group. Examples of halogen atoms include fluorine, chlorine, bromine, and iodine atoms, with chlorine, bromine, or iodine atoms being more preferred, chlorine or bromine atoms being even more preferred, and chlorine atoms being particularly preferred. In one embodiment, Y is preferably a halogen atom, and more preferably a chlorine atom.

[0104] Specific examples of divalent aromatic carboxylic acid halide compounds or divalent aromatic carboxylic acid compounds include isophthalic acid chloride, terephthalic acid chloride, isophthalic acid, and terephthalic acid.

[0105] [Characteristics of Aromatic Oxycarbonyl Compounds] In the aromatic oxycarbonyl compounds of the present invention, the equivalent amount of the aromatic ring oxycarbonyl group (active ester group equivalent) is preferably 180 g / eq. or more, more preferably 190 g / eq. or more, even more preferably 200 g / eq. or more, and 210 g / eq. or more. The upper limit is preferably 1,000 g / eq. or less, more preferably 800 g / eq. or less, even more preferably 700 g / eq. or less, particularly preferably 600 g / eq. or less, 500 g / eq. or less, 400 g / eq. or less, or 300 g / eq. or less.

[0106] The number-average molecular weight (Mn) of the aromatic oxycarbonyl compound of the present invention is preferably 5,000 or less, more preferably 4,000 or less, and even more preferably 3,500 or less or 3,000 or less, from the viewpoint of using it as a curing agent for epoxy resins in a resin composition. The lower limit of Mn is not particularly limited and can be, for example, 400 or more, 450 or more, 500 or more, etc. The Mn of the aromatic oxycarbonyl compound of the present invention can be measured as a polystyrene equivalent value by gel permeation chromatography (GPC).

[0107] In one embodiment, the aromatic oxycarbonyl compound of the present invention exhibits excellent solubility in organic solvents. As described in the <Solvent Solubility Evaluation> section below, when the aromatic oxycarbonyl compound is stirred and mixed with toluene, MEK (methyl ethyl ketone), or cyclohexanone at room temperature, it is preferably soluble at a solid content of 10% by mass or more, and more preferably soluble at a solid content of 40% by mass or more.

[0108] In one embodiment, the aromatic oxycarbonyl compound of the present invention exhibits excellent solubility in other resins. As described in the <Resin Solubility Evaluation> section below, when the aromatic oxycarbonyl compound is melt-mixed with a bisphenol A type liquid epoxy resin or a biphenyl aralkyl type epoxy resin at 150°C, it is preferably soluble at 10% by mass or more of the aromatic oxycarbonyl compound, and more preferably soluble at 40% by mass or more of the aromatic oxycarbonyl compound. Furthermore, when the mixture melted and mixed at 150°C is cooled to room temperature, it is preferably soluble (no precipitation) at 10% by mass or more of the aromatic oxycarbonyl compound, and more preferably soluble (no precipitation) at 40% by mass or more of the aromatic oxycarbonyl compound.

[0109] [Method for Producing Aromatic Oxycarbonyl Compounds] The method for producing aromatic oxycarbonyl compounds of the present invention includes a step of reacting a compound represented by formula (X-1) above with a compound represented by formula (X-2) above with a divalent aromatic carboxylic acid halide compound or a divalent aromatic carboxylic acid compound. The product according to the method for producing aromatic oxycarbonyl compounds of the present invention is preferably the aromatic oxycarbonyl compound of the present invention as described in the [Aromatic Oxycarbonyl Compound According to the First Embodiment] section or the [Aromatic Oxycarbonyl Compound According to the Second Embodiment] section.

[0110] <Raw Materials> The raw materials for the method of producing the aromatic oxycarbonyl compound of the present invention are the same as the compound represented by formula (X-1), the compound represented by formula (X-2), the divalent aromatic carboxylic acid halide compound, or the divalent aromatic carboxylic acid compound described in the section [Aromatic Oxycarbonyl Compound According to the Second Embodiment].

[0111] <Reaction Conditions> The reaction may proceed in a solvent-free system without the use of a solvent, or in an organic solvent system using an organic solvent. Examples of organic solvents that can be used in the reaction include ketone solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone; acetic acid ester solvents such as ethyl acetate, butyl acetate, cellosolve acetate, propylene glycol monomethyl ether acetate, and carbitol acetate; carbitol solvents such as cellosolve and butyl carbitol; aromatic hydrocarbon solvents such as toluene and xylene; and amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methyl-2-pyrrolidone. Organic solvents may be used individually or in combination of two or more.

[0112] A base may be used in the reaction. Examples of bases include alkali metal hydroxides such as sodium hydroxide (caustic soda) and potassium hydroxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; alkali metal bicarbonates such as sodium bicarbonate and potassium bicarbonate; and tertiary amines such as triethylamine, pyridine, and N,N-dimethyl-4-aminopyridine (DMAP). Alkali metal hydroxides or tertiary amines are preferred as bases, with tertiary amines being more preferred. Sodium hydroxide (caustic soda) is preferred as the alkali metal hydroxide. Triethylamine is preferred as the tertiary amine. A single base may be used, or two or more bases may be used in combination.

[0113] In the reaction, condensing agents and interlayer transfer catalysts may also be used. Any conventionally known catalysts that can be used in esterification reactions may be used.

[0114] The reaction temperature is not particularly limited as long as the condensation reaction proceeds, and may be in the range of 0 to 80°C, for example. The reaction time in step (i) is also not particularly limited as long as the structure of the desired aromatic oxycarbonyl compound is achieved, and may be in the range of 30 minutes to 8 hours, for example.

[0115] After the reaction, the resulting aromatic oxycarbonyl compound may be purified. For example, after the reaction, purification steps such as washing with water or microfiltration may be performed to remove by-product salts and excess starting materials from the system. Specifically, after the reaction, the amount of water necessary to dissolve the by-product salts is added, and the aqueous layer is discarded after standing liquid-liquid separation. If necessary, an acid is added to neutralize, and washing with water is repeated. After that, the aromatic oxycarbonyl compound can be obtained by purification to remove impurities through a dehydration step using chemicals or azeotropy, followed by distillation removal of the organic solvent if necessary. The organic solvent may be used as an organic solvent in the resin composition without completely removing it.

[0116] [Epoxy Resin Curing Agent] The aromatic oxycarbonyl compound of the present invention exhibits excellent solubility in other resins such as epoxy resins and organic solvents, and when combined with epoxy resins, it can produce a cured product that exhibits excellent flame retardancy, excellent dielectric properties, and good heat resistance, thereby achieving the flame retardancy, low transmission loss, and heat resistance required for 5G applications. Therefore, in one preferred embodiment, the aromatic oxycarbonyl compound of the present invention can be suitably used as an epoxy resin curing agent.

[0117] [Resin Composition] A resin composition can be produced using the aromatic oxycarbonyl compound of the present invention. The present invention also provides such a resin composition.

[0118] The resin composition of the present invention contains (A) the aromatic oxycarbonyl compound of the present invention and (B) an epoxy resin. The aromatic oxycarbonyl compound contained in the resin composition is as described in the sections [Aromatic Oxycarbonyl Compound According to the First Embodiment] and [Aromatic Oxycarbonyl Compound According to the Second Embodiment].

[0119] The resin composition of the present invention may further contain any optional components. Optional components include (C) curing accelerators, epoxy resin curing agents other than component (A) (hereinafter referred to as "component (D)"), (E) thermoplastic resins, (F) inorganic fillers, (G) thermosetting resins other than epoxy resins, (H) radical polymerizable resins, (I) organic solvents, (J) other additives, and the like. Each component included in the resin composition will be described in detail below.

[0120] <(A) Aromatic oxycarbonyl compound of the present invention> The resin composition of the present invention contains (A) the aromatic oxycarbonyl compound of the present invention. (A) The aromatic oxycarbonyl compound of the present invention may be used alone or in combination of two or more types.

[0121] The content of (A) the aromatic oxycarbonyl compound of the present invention in the resin composition is preferably 10% by mass or more, more preferably 20% by mass or more or 30% by mass or more, and even more preferably 40% by mass or more or 45% by mass or more, when the resin component in the resin composition is considered to be 100% by mass, from the viewpoint of obtaining a cured product exhibiting excellent dielectric properties and heat resistance. The upper limit of the content is preferably 90% by mass or less, more preferably 85% by mass or less, even more preferably 80% by mass or less, and particularly preferably 75% by mass or less, 70% by mass or less, 65% by mass or less, 60% by mass or less or 55% by mass or less, from the viewpoint of obtaining a cured product exhibiting excellent dielectric properties and heat resistance. Since the aromatic oxycarbonyl compound of the present invention has high solubility in epoxy resin, even if the content is high as described above, the aromatic oxycarbonyl compound and epoxy resin melt together, and a suitable cured product can be produced.

[0122] The content of (A) the aromatic oxycarbonyl compound of the present invention in the resin composition is preferably 1% by mass or more, more preferably 2% by mass or more, even more preferably 3% by mass or more, and particularly preferably 5% by mass or more or 7% by mass or more, when the nonvolatile components in the resin composition are considered to be 100% by mass, from the viewpoint of obtaining a cured product exhibiting excellent dielectric properties and heat resistance. The upper limit of the content is preferably 90% by mass or less, more preferably 85% by mass or less, even more preferably 80% by mass or less, and particularly preferably 75% by mass or less, from the viewpoint of obtaining a cured product exhibiting excellent dielectric properties and heat resistance. In one embodiment, it may be 70% by mass or less, 60% by mass or less, 50% by mass or less, 40% by mass or less, 30% by mass or less, 20% by mass or less, etc.

[0123] <(B) Epoxy Resin> The resin composition of the present invention contains (B) epoxy resin. The epoxy resin is a curable resin having epoxy groups and an epoxy equivalent of 5,000 g / eq. or less. (B) epoxy resin may be used alone or in combination of two or more types. The type of (B) epoxy resin is not particularly limited as long as it has one or more (preferably two or more) epoxy groups in one molecule. (B) Examples of epoxy resins include bixylenol-type epoxy resin, bisphenol-type epoxy resin (bisphenol A-type epoxy resin, bisphenol F-type epoxy resin, bisphenol S-type epoxy resin, bisphenol AF-type epoxy resin, bisphenol C-type epoxy resin, etc.), dicyclopentadiene-type epoxy resin, trisphenol-type epoxy resin, naphthol novolac-type epoxy resin, phenol novolac-type epoxy resin, tert-butyl-catechol-type epoxy resin, naphthalene-type epoxy resin, naphthol-type epoxy resin, anthracene-type epoxy resin, glycidylamine-type epoxy resin, glycidyl ester-type epoxy resin, cresol novolac-type epoxy resin, phenol aralkyl-type epoxy resin, biphenyl-type epoxy resin, biphenyl Examples include ylaralkyl epoxy resins, linear aliphatic epoxy resins, epoxy resins having a butadiene structure, alicyclic epoxy resins, heterocyclic epoxy resins, spiroring-containing epoxy resins, cyclohexane-type epoxy resins, cyclohexanedimethanol-type epoxy resins, naphthylene ether-type epoxy resins, trimethylol-type epoxy resins, tetraphenylethane-type epoxy resins, isocyanurate-type epoxy resins, phenolphthaleimidine-type epoxy resins, glycyrrhizol-type epoxy resins, alkylene oxy skeleton-containing epoxy resins, fluorene structure-containing epoxy resins, halogenated epoxy resins, etc. Bisphenol-type epoxy resins or biphenylaralkyl-type epoxy resins are preferred, and bisphenol A-type epoxy resins or biphenylaralkyl-type epoxy resins are more preferred. (B) The epoxy resin may be used alone or in combination of two or more types.

[0124] The resin composition of the present invention preferably contains an epoxy resin having two or more epoxy groups in one molecule as component (B). From the viewpoint of significantly obtaining the desired effects of the present invention, the ratio of the epoxy resin having two or more epoxy groups in one molecule to 100% by mass of epoxy resin (B) is preferably 50% by mass or more, more preferably 60% by mass or more, and particularly preferably 70% by mass or more.

[0125] (B) Epoxy resins include epoxy resins that are liquid at 20°C (hereinafter sometimes referred to as "liquid epoxy resins") and epoxy resins that are solid at 20°C (hereinafter sometimes referred to as "solid epoxy resins"). The resin composition of the present invention may contain only liquid epoxy resin as component (B), only solid epoxy resin, or a combination of liquid epoxy resin and solid epoxy resin. In one embodiment, the resin composition of the present invention preferably contains a combination of liquid epoxy resin and solid epoxy resin.

[0126] As the liquid epoxy resin, a liquid epoxy resin having two or more epoxy groups in one molecule is preferred.

[0127] Examples of liquid epoxy resins include glycirol-type epoxy resins, bisphenol-type epoxy resins (bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol AF type epoxy resin, bisphenol C type epoxy resin, etc.), naphthalene-type epoxy resins, glycidyl ester-type epoxy resins, glycidylamine-type epoxy resins, phenol novolac-type epoxy resins, alicyclic epoxy resins having an ester skeleton, cyclohexanedimethanol-type epoxy resins, cyclic aliphatic glycidyl ethers, epoxy resins having a butadiene structure, dicyclopentadiene-type epoxy resins, alkylene oxy-backbone-containing epoxy resins, and fluorene-containing epoxy resins. Bisphenol-type epoxy resins are preferred, and bisphenol A type epoxy resins are more preferred.

[0128] Specific examples of liquid epoxy resins include "EX-992L" from Nagase ChemteX, "YX7400" from Mitsubishi Chemical Corporation, "HP4032", "HP4032D", and "HP4032SS" from DIC Corporation (naphthalene-type epoxy resin); "828US", "jER828EL", "828EL", "825", and "Epicoat 828EL" from Mitsubishi Chemical Corporation, and "850-S" from DIC Corporation (bisphenol A-type epoxy resin); and "jER" from Mitsubishi Chemical Corporation. 807, 1750 (Bisphenol F type epoxy resin); Mitsubishi Chemical's "jER152" (Phenol novolac type epoxy resin); Mitsubishi Chemical's "630", "630LSD", "604" (Glycidylamine type epoxy resin); ADEKA's "ED-523T" (Glysilol type epoxy resin); ADEKA's "EP-3950L", "EP-3980S" (Glycidylamine type epoxy resin); ADEKA's "EP-40 88S (dicyclopentadiene type epoxy resin); ZX-1059 (a mixture of bisphenol A type epoxy resin and bisphenol F type epoxy resin) manufactured by Nippon Steel Chemical & Material Co., Ltd.; EX-721 (glycidyl ester type epoxy resin) manufactured by Nagase ChemteX Co., Ltd.; EX-991L (alkylene oxy skeleton-containing epoxy resin) manufactured by Nagase ChemteX Co., Ltd.; Celoxide 2021P (alicyclic epoxy resin with an ester skeleton) manufactured by Daicel Corporation. Examples include: resins such as "PB-3600" from Daicel Corporation, "JP-100" and "JP-200" from Nippon Soda Co., Ltd. (epoxy resins having a butadiene structure); "ZX1658" and "ZX1658GS" from Nippon Steel Chemical & Material Co., Ltd. (liquid 1,4-glycidylcyclohexane type epoxy resins); "EG-280" from Osaka Gas Chemical Co., Ltd. (fluorene structure-containing epoxy resin); and "EX-201" from Nagase ChemteX Corporation (resorcinol type epoxy resin). These may be used individually or in combination of two or more types.

[0129] As the solid epoxy resin, a solid epoxy resin having two or more epoxy groups per molecule is preferred, and an aromatic solid epoxy resin having three or more epoxy groups per molecule is more preferred.

[0130] Examples of solid epoxy resins include bixylenol-type epoxy resins, naphthalene-type epoxy resins, naphthalene-type tetrafunctional epoxy resins, naphthol novolac-type epoxy resins, cresol novolac-type epoxy resins, dicyclopentadiene-type epoxy resins, trisphenol-type epoxy resins, naphthol-type epoxy resins, biphenyl-type epoxy resins, biphenyl aralkyl-type epoxy resins, naphthylene ether-type epoxy resins, anthracene-type epoxy resins, bisphenol-type epoxy resins (bisphenol A-type epoxy resins, bisphenol AF-type epoxy resins, etc.), phenol aralkyl-type epoxy resins, tetraphenylethane-type epoxy resins, phenolphthalein-type epoxy resins, and fluorene-structure-containing epoxy resins, with biphenyl aralkyl-type epoxy resins being preferred.

[0131] Specific examples of solid epoxy resins include, for example, DIC's "HP4032H" (naphthalene-type epoxy resin); DIC's "HP-4700" and "HP-4710" (naphthalene-type tetrafunctional epoxy resins); DIC's "N-690" and "N-695" (cresol novolac-type epoxy resins); DIC's "HP-7200," "HP-7200HH," "HP-7200H," and "HP-7200L" (dicyclopentadiene-type epoxy resins); DIC's "EXA-7311," "EXA-7311-G3," and "EXA-731 "1-G4", "EXA-7311-G4S", "HP-6000", "HP-6000L" (naphthylene ether type epoxy resin); "EPPN-502H" (trisphenol type epoxy resin) manufactured by Nippon Kayaku Co., Ltd.; "NC7000L" (naphthol novolac type epoxy resin) manufactured by Nippon Kayaku Co., Ltd.; "NC-3000", "NC-3000L", "NC-3000FH", "NC-3100", "NC-3000H" (biphenyl aralkyl type epoxy resin) manufactured by Nippon Kayaku Co., Ltd.; "ESN475V", "ESN41" manufactured by Nippon Steel Chemical & Material Co., Ltd. 00V (naphthalene-type epoxy resin); ESN485 (naphthol-type epoxy resin) manufactured by Nippon Steel Chemical & Material Co., Ltd.; ESN375 (dihydroxynaphthalene-type epoxy resin) manufactured by Nippon Steel Chemical & Material Co., Ltd.; YX4000H, YX4000, YX4000HK, YL7890 (bixylenol-type epoxy resin) manufactured by Mitsubishi Chemical Corporation; YL6121 (biphenyl-type epoxy resin) manufactured by Mitsubishi Chemical Corporation; YX8800 (anthracene-type epoxy resin) manufactured by Mitsubishi Chemical Corporation; YX77 Examples include "00" (phenol aralkyl type epoxy resin); "PG-100" and "CG-500" manufactured by Osaka Gas Chemical Co., Ltd.; "YL7760" (bisphenol AF type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "YL7800" (fluorene structure-containing epoxy resin) manufactured by Mitsubishi Chemical Corporation; "jER1010" (bisphenol A type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "jER1031S" (tetraphenylethane type epoxy resin) manufactured by Mitsubishi Chemical Corporation; and "WHR991S" (phenolphthaleinidine type epoxy resin) manufactured by Nippon Kayaku Co., Ltd.These can be used individually or in combination of two or more types.

[0132] (B) The epoxy equivalent of the epoxy resin is preferably 50 to 5,000 g / eq. The lower limit of the epoxy equivalent is preferably 50 g / eq. or more, more preferably 60 g / eq. or more, even more preferably 80 g / eq. or more, and particularly preferably 110 g / eq. or more, as mentioned above. The upper limit of the epoxy equivalent is preferably 5,000 g / eq. or less, more preferably 3,000 g / eq. or less, even more preferably 2,000 g / eq. or less, even more preferably 1,000 g / eq. or less, and particularly preferably 500 g / eq. or less. The epoxy equivalent is the mass of epoxy resin containing one equivalent of epoxy groups and can be measured according to JIS K7236.

[0133] (B) The weight-average molecular weight (Mw) of the epoxy resin is preferably 100 to 5,000, more preferably 250 to 3,000, and even more preferably 400 to 1,500. The weight-average molecular weight (Mw) of the epoxy resin can be measured as a polystyrene equivalent by the GPC method.

[0134] From the viewpoint of obtaining a cured product exhibiting excellent dielectric properties and heat resistance, the content of (B) epoxy resin in the resin composition is preferably 5% by mass or more, more preferably 10% by mass or more, even more preferably 15% by mass or more or 20% by mass or more, and particularly preferably 25% by mass or more, 30% by mass or more, 35% by mass or more or 40% by mass or more, when the total resin component in the resin composition is considered to be 100% by mass. The upper limit of the content is preferably 80% by mass or less or 75% by mass or less, more preferably 70% by mass or less or 65% by mass or less, and even more preferably 60% by mass or less or 55% by mass or less, from the viewpoint of obtaining a cured product exhibiting excellent dielectric properties and heat resistance.

[0135] From the viewpoint of obtaining a cured product exhibiting excellent dielectric properties and heat resistance, the content of (B) epoxy resin in the resin composition is preferably 1% by mass or more, more preferably 3% by mass or more, even more preferably 5% by mass or more, and particularly preferably 8% by mass or more or 10% by mass or more, when the nonvolatile components in the resin composition are considered to be 100% by mass. The upper limit of the content is preferably 80% by mass or less or 75% by mass or less, more preferably 70% by mass or less or 65% by mass or less, even more preferably 60% by mass or less or 55% by mass or less, and particularly preferably 50% by mass or less, 45% by mass or less or 40% by mass or less, from the viewpoint of obtaining a cured product exhibiting excellent dielectric properties and heat resistance. In one embodiment, it may be 35% by mass or less, 30% by mass or less, 25% by mass or less, 20% by mass or less, etc.

[0136] The total content of (A) the aromatic oxycarbonyl compound of the present invention and (B) the epoxy resin in the resin composition is preferably 50% by mass or more or 60% by mass or more, more preferably 70% by mass or more or 75% by mass or more, even more preferably 80% by mass or more or 85% by mass or more, and particularly preferably 90% by mass or more, 95% by mass or more or 99% by mass or more, when the resin component in the resin composition is considered as 100% by mass, from the viewpoint of obtaining a cured product exhibiting excellent dielectric properties and heat resistance. The upper limit of the content is not particularly limited and may be determined according to the properties required of the resin composition, for example, it may be 100% by mass or 99.9% by mass or less.

[0137] The total content of (A) the aromatic oxycarbonyl compound of the present invention and (B) the epoxy resin in the resin composition is preferably 2% by mass or more, more preferably 5% by mass or more, even more preferably 8% by mass or more or 10% by mass or more, and particularly preferably 12% by mass or more or 15% by mass or more, when the nonvolatile components in the resin composition are considered to be 100% by mass, from the viewpoint of obtaining a cured product that exhibits excellent dielectric properties and heat resistance. The upper limit of the content is not particularly limited and may be determined according to the properties required of the resin composition, but for example it may be 100% by mass, 99.9% by mass or less, 99% by mass or less, 90% by mass or less, 80% by mass or less, 70% by mass or less, 60% by mass or less, 50% by mass or less, 40% by mass or less, 30% by mass or less, 20% by mass or less, etc.

[0138] In the resin composition of the present invention, the mass ratio [component (A) / component (B)] of the aromatic oxycarbonyl compound of the present invention to (B) epoxy resin is preferably 0.1 or more, more preferably 0.3 or more or 0.4 or more, even more preferably 0.5 or more, 0.6 or more or 0.7 or more. The upper limit of the mass ratio [component (A) / component (B)] is preferably 10 or less, more preferably 8 or less, even more preferably 5 or less, particularly preferably 3 or less, 2.5 or less, 2.0 or less, 1.8 or less, 1.5 or less or 1.2 or less.

[0139] <(C) Curing Accelerator> The resin composition of the present invention may further contain (C) a curing accelerator as an optional component, and it is preferable to contain (C) a curing accelerator. (C) The curing accelerator has the function of a curing catalyst that accelerates the curing of (A) the aromatic oxycarbonyl compound of the present invention and (B) the epoxy resin.

[0140] (C) Examples of curing accelerators include phosphorus-based curing accelerators, urea-based curing accelerators, guanidine-based curing accelerators, imidazole-based curing accelerators, metal-based curing accelerators, amine-based curing accelerators, etc. (C) The curing accelerator preferably contains an amine-based curing accelerator. (C) The curing accelerator may be used alone or in combination of two or more types.

[0141] Examples of amine-based curing accelerators include trialkylamines such as triethylamine and tributylamine, pyridines such as 4-dimethylaminopyridine, benzyldimethylamine, 2,4,6-tris(dimethylaminomethyl)phenol, and 1,8-diazabicyclo(5,4,0)-undecene, with pyridines being preferred and 4-dimethylaminopyridine being more preferred. These may be used individually or in combination of two or more.

[0142] As amine-based curing accelerators, commercially available products may be used, such as "MY-25" manufactured by Ajinomoto Fine Techno Co., Ltd. and "DMAP" manufactured by Koei Chemical Industry Co., Ltd.

[0143] Examples of phosphorus-based curing accelerators include aliphatic phosphonium salts such as tetrabutylphosphonium bromide, tetrabutylphosphonium chloride, tetrabutylphosphonium acetate, tetrabutylphosphonium decanoate, tetrabutylphosphonium laurate, bis(tetrabutylphosphonium) pyromelitate, tetrabutylphosphonium hydrogen hexahydrophthalate, tetrabutylphosphonium 2,6-bis[(2-hydroxy-5-methylphenyl)methyl]-4-methylphenolate, di-tert-butylmethylphosphonium tetraphenylborate; methyltriphenylphosphonium bromide, ethyltriphenylphosphonium bromide, propyltriphenylphosphonium bromide, butyltriphenylphosphonium bromide, benzyltriphenylphosphonium chloride, tetraphenylphosphonium bromide, p-tolyltriphenylphosphonium tetra-p-tolylborate, tetraphenylphosphonium bromide, and tetraphenylphosphonium bromide. Aromatic phosphonium salts such as tetraphenylborate, tetraphenylphosphonium tetra-p-tolylborate, triphenylethylphosphonium tetraphenylborate, tris(3-methylphenyl)ethylphosphonium tetraphenylborate, tris(2-methoxyphenyl)ethylphosphonium tetraphenylborate, (4-methylphenyl)triphenylphosphonium thiocyanate, tetraphenylphosphonium thiocyanate, and butyltriphenylphosphonium thiocyanate; aromatic phosphine-borane complexes such as triphenylphosphine and triphenylborane; aromatic phosphine-quinone addition products such as triphenylphosphine-p-benzoquinone addition products; aliphatic phosphines such as tributylphosphine, tri-tert-butylphosphine, trioctylphosphine, di-tert-butyl(2-butenyl)phosphine, di-tert-butyl(3-methyl-2-butenyl)phosphine, and tricyclohexylphosphine;Dibutylphenylphosphine, di-tert-butylphenylphosphine, methyldiphenylphosphine, ethyldiphenylphosphine, butyldiphenylphosphine, diphenylcyclohexylphosphine, triphenylphosphine, tri-o-tolylphosphine, tri-m-tolylphosphine, tri-p-tolylphosphine, tris(4-ethylphenyl)phosphine, tris(4-propylphenyl)phosphine, tris(4-isopropylphenyl)phosphine, tris(4-butylphenyl)phosphine, tris(4-tert-butylphenyl)phosphine, tris(2,4-dimethylphenyl)phosphine, tris(2,5-dimethylphenyl)phosphine, tris(2,6-dimethylphenyl)phosphine Examples include aromatic phosphines such as tris(3,5-dimethylphenyl)phosphine, tris(2,4,6-trimethylphenyl)phosphine, tris(2,6-dimethyl-4-ethoxyphenyl)phosphine, tris(2-methoxyphenyl)phosphine, tris(4-methoxyphenyl)phosphine, tris(4-ethoxyphenyl)phosphine, tris(4-tert-butoxyphenyl)phosphine, diphenyl-2-pyridylphosphine, 1,2-bis(diphenylphosphino)ethane, 1,3-bis(diphenylphosphino)propane, 1,4-bis(diphenylphosphino)butane, 1,2-bis(diphenylphosphino)acetylene, and 2,2'-bis(diphenylphosphino)diphenyl ether. These may be used individually or in combination of two or more.

[0144] Examples of urea-based curing accelerators include aliphatic dimethylureas such as 1,1-dimethylurea, 1,1,3-trimethylurea, 3-ethyl-1,1-dimethylurea, 3-cyclohexyl-1,1-dimethylurea, and 3-cyclooctyl-1,1-dimethylurea; 3-phenyl-1,1-dimethylurea, 3-(4-chlorophenyl)-1,1-dimethylurea, 3-(3,4-dichlorophenyl)-1,1-dimethylurea, 3-(3-chloro-4-methylphenyl)-1,1-dimethylurea, 3-(2-methylphenyl)-1,1-dimethylurea, 3-(4-methylphenyl)-1,1-dimethylurea, and 3-(3,4-dimethylphenyl)-1,1-dimethylurea. Aromatic dimethylureas such as toluene urea, 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), N,N-(4-methyl-1,3-phenylene)bis(N',N'-dimethylurea) [toluenebisdimethylurea], etc. These may be used individually or in combination of two or more.

[0145] Examples of guanidine-based curing accelerators include dicyandiamide, 1-methylguanidine, 1-ethylguanidine, 1-cyclohexylguanidine, 1-phenylguanidine, 1-(o-tolyl)guanidine, dimethylguanidine, diphenylguanidine, trimethylguanidine, tetramethylguanidine, pentamethylguanidine, 1,5,7-triazabicyclo[4.4.0]deca-5-ene, 7-methyl-1,5,7-triazabicyclo[4.4.0]deca-5-ene, 1-methylbiguanide, 1-ethylbiguanide, 1-n-butylbiguanide, 1-n-octadecylbiguanide, 1,1-dimethylbiguanide, 1,1-diethylbiguanide, 1-cyclohexylbiguanide, 1-allylbiguanide, 1-phenylbiguanide, and 1-(o-tolyl)biguanide. These may be used individually or in combination of two or more types.

[0146] Examples of imidazole-based curing accelerators include 2-methylimidazole, 2-undecylimidazole, 2-heptadecylimidazole, 1,2-dimethylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 2-phenyl-4-methylimidazole, 1-benzyl-2-methylimidazole, 1-benzyl-2-phenylimidazole, 1-cyanoethyl-2-methylimidazole, 1-cyanoethyl-2-undecylimidazole, 1-cyanoethyl-2-ethyl-4-methylimidazole, 1-cyanoethyl-2-phenylimidazole, 1-cyanoethyl-2-undecylimidazolium trimellitate, 1-cyanoethyl-2-phenylimidazolium trimellitate, and 2,4-diamino-6-[2'-methylimidazolyl-(1')]-ethyl-s-triazine 2,4-diamino-6-[2'-undecylimidazolyl-(1')]-ethyl-s-triazine, 2,4-diamino-6-[2'-ethyl-4'-methylimidazolyl-(1')]-ethyl-s-triazine, 2,4-diamino-6-[2'-methylimidazolyl-(1')]-ethyl-s-triazine isocyanurate adduct, 2-phenylimidazole isocyanurate adduct, 2-phenyl- Examples include imidazole compounds such as 4,5-dihydroxymethylimidazole, 2-phenyl-4-methyl-5-hydroxymethylimidazole, 2,3-dihydro-1H-pyrrolo[1,2-a]benzimidazole, 1-dodecyl-2-methyl-3-benzylimidazolium chloride, 2-methylimidazoline, and 2-phenylimidazoline, as well as adducts of imidazole compounds with epoxy resins.

[0147] Examples of commercially available imidazole-based curing accelerators include "1B2PZ", "2E4MZ", "2MZA-PW", "2MZ-OK", "2MA-OK", "2MA-OK-PW", "2P4MZ", "2PHZ", "2PHZ-PW", "Cl1Z", "Cl1Z-CN", "Cl1Z-CNS", and "C11Z-A" from Shikoku Chemicals Corporation; and "P200-H50" from Mitsubishi Chemical Corporation. These may be used individually or in combination of two or more types.

[0148] Examples of metal-based hardening accelerators include organometallic complexes or organometallic salts of metals such as cobalt, copper, zinc, iron, nickel, manganese, and tin. Specific examples of organometallic complexes include organocobalt complexes such as cobalt(II) acetylacetonate and cobalt(III) acetylacetonate, organocopper complexes such as copper(II) acetylacetonate, organozinc complexes such as zinc(II) acetylacetonate, organoiron complexes such as iron(III) acetylacetonate, organonickel complexes such as nickel(II) acetylacetonate, and organomanganese complexes such as manganese(II) acetylacetonate. Examples of organometallic salts include zinc octoate, tin octoate, zinc naphthenate, cobalt naphthenate, tin stearate, and zinc stearate. These may be used individually or in combination of two or more.

[0149] When the resin composition of the present invention contains (C) a curing accelerator, the content of (C) the curing accelerator in the resin composition may be determined according to the properties required for the resin composition, but when the resin components in the resin composition are taken as 100% by mass, it is preferably 10% by mass or less, more preferably 5% by mass or less, even more preferably 1% by mass or less, and particularly preferably 0.7% by mass or less. The lower limit is preferably 0.001% by mass or more, more preferably 0.01% by mass or more or 0.05% by mass or more, and even more preferably 0.1% by mass or more or 0.2% by mass or more.

[0150] When the resin composition of the present invention contains (C) a curing accelerator, the content of (C) the curing accelerator in the resin composition may be determined according to the properties required for the resin composition, but when the nonvolatile components in the resin composition are taken as 100% by mass, it is preferably 5% by mass or less, more preferably 1% by mass or less, even more preferably 0.5% by mass or less, and particularly preferably 0.1% by mass or less. The lower limit is preferably 0.0001% by mass or more, more preferably 0.001% by mass or more, even more preferably 0.01% by mass or more, and particularly preferably 0.02% by mass or more.

[0151] <Epoxy resin curing agents other than component (A)> The resin composition of the present invention may further contain an epoxy resin curing agent other than component (A) (component (D)) as an optional component. Component (D) may be used alone or in combination of two or more types.

[0152] Examples of epoxy resin curing agents other than component (A) include active ester curing agents other than component (A), phenol curing agents, carbodiimide curing agents, acid anhydride curing agents, amine curing agents, benzoxazine curing agents, cyanate ester curing agents, thiol curing agents, and the like.

[0153] As active ester curing agents other than component (A), compounds that do not fall under component (A) and have one or more oxycarbonyl groups (active ester groups) in one molecule can be used. Among these, as active ester curing agents other than component (A), compounds having two or more highly reactive ester groups in one molecule, such as phenol esters, thiophenol esters, N-hydroxyamine esters, and esters of heterocyclic hydroxy compounds, are preferred. The active ester curing agent is preferably obtained by a condensation reaction between a carboxylic acid compound and / or a thiocarboxylic acid compound and a hydroxy compound and / or a thiol compound. In particular, from the viewpoint of improving heat resistance, an active ester curing agent obtained from a carboxylic acid compound and a hydroxy compound is preferred, and an active ester curing agent obtained from a carboxylic acid compound and a phenol compound and / or a naphthol compound is more preferred. In one embodiment, the active ester curing agent may be an active ester curing agent obtained from a carboxylic acid compound and a phenol compound or a naphthol compound, or an active ester curing agent obtained from a carboxylic acid compound and a phenol compound and a naphthol compound.

[0154] Examples of carboxylic acid compounds include benzoic acid, acetic acid, succinic acid, maleic acid, itaconic acid, phthalic acid, isophthalic acid, terephthalic acid, pyromellitic acid, and dimer acid.

[0155] Examples of phenol compounds or naphthol compounds include hydroquinone, resorcinol, bisphenol A, bisphenol F, bisphenol S, phenolphthalein, methylated bisphenol A, methylated bisphenol F, methylated bisphenol S, phenol, o-cresol, m-cresol, p-cresol, phenylphenol, catechol, α-naphthol, β-naphthol, 1,5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 2,6-dihydroxynaphthalene, dihydroxybenzophenone, trihydroxybenzophenone, tetrahydroxybenzophenone, phloroglucin, benzenetriol, dicyclopentadiene-type diphenol compounds, phenol novolac, and dimerol. Here, "dicyclopentadiene-type diphenol compound" refers to a diphenol compound obtained by the condensation of two phenol molecules with one dicyclopentadiene molecule.

[0156] (A) Examples of preferred active ester curing agents other than component (A) include active ester resins containing a dicyclopentadiene-type diphenol structure (hereinafter also referred to as "dicyclopentadiene-type active ester resin"), active ester resins containing a naphthalene structure, phosphorus-containing active ester resins, active ester resins containing acetylated phenol novolacs, active ester resins containing benzoylated phenol novolacs, and active ester resins containing a butadiene structure. Among these, active ester resins containing a naphthalene structure, active ester resins containing a dicyclopentadiene-type diphenol structure, or active ester resins containing a butadiene structure are preferred, active ester resins containing a naphthalene structure or active ester resins containing a dicyclopentadiene-type diphenol structure are more preferred, and active ester resins containing a dicyclopentadiene-type diphenol structure are even more preferred. "Dicyclopentadiene-type diphenol structure" refers to a divalent structural unit consisting of phenylene-dicyclopentylene-phenylene.

[0157] Other specific examples of active ester curing agents other than component (A) include active ester compounds having a dimer acid skeleton and / or a dimer ol skeleton in their molecules. The resin composition of the present invention may or may not contain an active ester compound having a dimer acid skeleton and / or a dimer ol skeleton in its molecule as an active ester curing agent other than component (A). That is, in one embodiment, the present invention can exclude resin compositions containing an active ester compound having a dimer acid skeleton and / or a dimer ol skeleton in its molecule.

[0158] The equivalent amount of oxycarbonyl groups (active ester group equivalent, functional group equivalent) of the active ester-based curing agent other than component (A) is preferably 180 g / eq. or more, 190 g / eq. or more, 200 g / eq. or more, or 210 g / eq. or more. The upper limit of the equivalent amount of oxycarbonyl groups (active ester group equivalent, functional group equivalent) can be, for example, 1,000 g / eq. or less, 750 g / eq. or less, 700 g / eq. or less, 600 g / eq. or less, 500 g / eq. or less, 400 g / eq. or less, or 300 g / eq. or less. Therefore, in one embodiment, the equivalent amount of oxycarbonyl groups (active ester group equivalent, functional group equivalent) of the active ester-based curing agent other than component (A) is 180 to 1,000 g / eq., 190 to 750 g / eq. It may be 200-700 g / eq., 200-600 g / eq., 200-500 g / eq., 200-400 g / eq., or 210-300 g / eq.

[0159] (A) Commercially available active ester curing agents other than component include: Active ester resins containing a dicyclopentadiene-type diphenol structure such as "EXB9451", "EXB9460", "EXB9460S", "HPC-8000-65T", "EXB-8000H", "HPC-8000L-65MT", and "EXB-8000L-65TM" (manufactured by DIC Corporation); and naphthalene-type active ester resins containing a naphthalene structure such as "EXB-9416-70BK", "EXB-8100L-65T", "EXB-8150L-65T", "HPC-8150-62T", and "EXB-8100L-65T". Examples include "EXB-8" (manufactured by DIC Corporation), "PC1300-02-65T", and "PC1300-02-65MA" (manufactured by Air Water Corporation); "EXB-9401" (manufactured by DIC Corporation) as a phosphorus-containing active ester resin; "DC808" (manufactured by Mitsubishi Chemical Corporation) as an active ester resin containing an acetylated phenol novolac; and "YLH1026" (manufactured by Mitsubishi Chemical Corporation), "YLH1030" (manufactured by Mitsubishi Chemical Corporation), "YLH1048" (manufactured by Mitsubishi Chemical Corporation), and "EXB-8500-65T" (manufactured by DIC Corporation) as active ester resins that are benzoylated phenol novolacs.

[0160] As a phenolic curing agent, a curing agent having one or more, preferably two or more, hydroxyl groups (phenolic hydroxyl groups) bonded to aromatic rings such as benzene rings and naphthalene rings per molecule may be used. From the viewpoint of heat resistance and water resistance, a phenolic curing agent having a novolac structure is preferred. Furthermore, from the viewpoint of adhesion to the adherend, a nitrogen-containing phenolic curing agent is preferred, and a triazine skeleton-containing phenolic curing agent is more preferred. Among these, a triazine skeleton-containing phenol novolac resin is preferred from the viewpoint of highly satisfying heat resistance, water resistance, and adhesion.

[0161] Specific examples of phenolic curing agents include, for example, UBE's "MEH-7700", "MEH-7810", "MEH-7851", "MEH-7600", "MEH-7851", and "MEH-8000H"; Nippon Kayaku's "NHN", "CBN", "GPH", "GPH-65", and "GPH-103"; and Nippon Steel Chemical & Material's "SN-170" and "SN-1 Examples include "80", "SN-190", "SN-475", "SN-485", "SN-495", "SN-375", "SN-395"; and DIC Corporation's "LA-7052", "LA-7054", "LA-3018", "LA-3018-50P", "LA-1356", "TD-2090", "TD2131", "TD-2090-60M", "KA-1160", etc. These may be used individually or in combination of two or more types.

[0162] Examples of carbodiimide-based curing agents include curing agents having one or more, preferably two or more, carbodiimide structures in one molecule, such as aliphatic biscarbodiimides such as tetramethylene-bis(t-butylcarbodiimide) and cyclohexanebis(methylene-t-butylcarbodiimide); biscarbodiimides such as aromatic biscarbodiimides such as phenylene-bis(xylylcarbodiimide); and aliphatic polycarbodiimides such as polyhexamethylenecarbodiimide, polytrimethylhexamethylenecarbodiimide, polycyclohexylenecarbodiimide, poly(methylenebiscyclohexylenecarbodiimide), and poly(isophoronecarbodiimide). Examples of polycarbodiimides include poly(phenylenecarbodiimide), poly(naphthylenecarbodiimide), poly(trylenecarbodiimide), poly(methyldiisopropylphenylenecarbodiimide), poly(triethylphenylenecarbodiimide), poly(diethylphenylenecarbodiimide), poly(triisopropylphenylenecarbodiimide), poly(diisopropylphenylenecarbodiimide), poly(xylylenecarbodiimide), poly(tetramethylxylylenecarbodiimide), poly(methylenediphenylenecarbodiimide), and aromatic polycarbodiimides such as poly[methylenebis(methylphenylene)carbodiimide]; and others. These may be used individually or in combination of two or more types.

[0163] Examples of commercially available carbodiimide-based curing agents include "Carbodilite V-02B," "Carbodilite V-03," "Carbodilite V-04K," "Carbodilite V-07," and "Carbodilite V-09" from Nisshinbo Chemical Co., Ltd., and "Stavaxol P," "Stavaxol P400," and "Hycazil 510" from Lanxess Corporation. These may be used individually or in combination of two or more types.

[0164] Examples of acid anhydride-based curing agents include curing agents having one or more acid anhydride groups in one molecule, and curing agents having two or more acid anhydride groups in one molecule are preferred. Specific examples of acid anhydride-based curing agents include phthalic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, methyltetrahydrophthalic anhydride, methylhexahydrophthalic anhydride, methylnadic anhydride, hydrogenated methylnadic anhydride, trialkyltetrahydrophthalic anhydride, dodecenyl succinic anhydride, 5-(2,5-dioxotetrahydro-3-furanyl)-3-methyl-3-cyclohexen-1,2-dicarboxylic acid anhydride, trimellitic anhydride, pyromellitic anhydride, and bensophenone tetracarboxylic acid di Examples include anhydrides, biphenyltetracarboxylic acid dianhydride, naphthalenetetracarboxylic acid dianhydride, oxydiphthalic acid dianhydride, 3,3'-4,4'-diphenylsulfontetracarboxylic acid dianhydride, 1,3,3a,4,5,9b-hexahydro-5-(tetrahydro-2,5-dioxo-3-furanyl)-naphtho[1,2-C]furan-1,3-dione, ethylene glycol bis(anhydrotrimellitate), and polymer-type acid anhydrides such as styrene-maleic acid resin obtained by copolymerizing styrene and maleic acid. These may be used individually or in combination of two or more types.

[0165] Commercially available acid anhydride-based curing agents include "HNA-100," "MH-700," "MTA-15," "DDSA," and "OSA" from Shin Nippon Rika Co., Ltd.; "YH-306" and "YH-307" from Mitsubishi Chemical Corporation; "HN-2200" and "HN-5500" from Resona Co., Ltd.; and "EF-30," "EF-40," "EF-60," and "EF-80" from Clay Valley Corporation. These may be used individually or in combination of two or more types.

[0166] Examples of amine-based curing agents include curing agents having one or more, preferably two or more, amino groups in one molecule. The amino groups in the amine-based curing agent are preferably primary or secondary amino groups, with primary amino groups being more preferred. Examples of amine-based curing agents include aliphatic amines, polyetheramines, alicyclic amines, aromatic amines, and the like, among which aromatic amines are preferred from the viewpoint of achieving the desired effects of the present invention. The amine-based curing agent is preferably a primary or secondary amine, with primary amines being more preferred.

[0167] Specific examples of amine-based curing agents include 4,4'-methylenebis(2,6-dimethylaniline), 4,4'-diaminodiphenylmethane, 4,4'-diaminodiphenylsulfone, 3,3'-diaminodiphenylsulfone, m-phenylenediamine, m-xylylenediamine, diethyltoluenediamine, 4,4'-diaminodiphenyl ether, 3,3'-dimethyl-4,4'-diaminobiphenyl, 2,2'-dimethyl-4,4'-diaminobiphenyl, 3,3'-dihydroxybenzidine, and 2,2-bis(3-amino-4-hydroxyphenyl) Examples include propane, 3,3-dimethyl-5,5-diethyl-4,4-diphenylmethanediamine, 2,2-bis(4-aminophenyl)propane, 2,2-bis(4-(4-aminophenoxy)phenyl)propane, 1,3-bis(3-aminophenoxy)benzene, 1,3-bis(4-aminophenoxy)benzene, 1,4-bis(4-aminophenoxy)benzene, 4,4'-bis(4-aminophenoxy)biphenyl, bis(4-(4-aminophenoxy)phenyl)sulfone, bis(4-(3-aminophenoxy)phenyl)sulfone, etc. Amine-based curing agents may be commercially available products, such as "SEIKACURE-S" from Seika Corporation, "KAYABOND C-200S," "KAYABOND C-100," "Kayahard A-A," "Kayahard A-B," and "Kayahard A-S" from Nippon Kayaku Co., Ltd., "Epicure W" from Mitsubishi Chemical Corporation, and "DTDA" from Sumitomo Seika Co., Ltd. These may be used individually or in combination of two or more types.

[0168] Specific examples of benzoxazine-based curing agents include "JBZ-OP100D" and "ODA-BOZ" from JFE Chemical Co., Ltd.; "HFB2006M" from Showa Polymer Co., Ltd.; and "P-d" and "F-a" from Shikoku Chemicals Co., Ltd. These may be used individually or in combination of two or more types.

[0169] Examples of cyanate ester curing agents include bifunctional cyanate resins such as bisphenol A dicyanate, polyphenol cyanate (oligo(3-methylene-1,5-phenylene cyanate)), 4,4'-methylenebis(2,6-dimethylphenyl cyanate), 4,4'-ethylidene diphenyl dicyanate, hexafluorobisphenol A dicyanate, 2,2-bis(4-cyanate)phenylpropane, 1,1-bis(4-cyanatephenylmethane), bis(4-cyanate-3,5-dimethylphenyl)methane, 1,3-bis(4-cyanatephenyl-1-(methylethylidene))benzene, bis(4-cyanatephenyl) thioether, and bis(4-cyanatephenyl) ether; polyfunctional cyanate resins derived from phenol novolacs and cresol novolacs; and prepolymers in which these cyanate resins are partially triazined. Specific examples of cyanate ester curing agents include "PT30" and "PT60" (both phenol novolac type polyfunctional cyanate ester resins) manufactured by arxada, "BA230" and "BA230S75" (prepolymers in which part or all of bisphenol A dicyanate is triazined and trimerized). These may be used individually or in combination of two or more types.

[0170] Examples of thiol-based curing agents include trimethylolpropane tris(3-mercaptopropionate), pentaerythritol tetrakis(3-mercaptobutyrate), and tris(3-mercaptopropyl) isocyanurate. These may be used individually or in combination of two or more types.

[0171] When the resin composition of the present invention contains component (D), the content of component (D) in the resin composition may be determined according to the properties required for the resin composition. However, when the total resin component in the resin composition is taken as 100% by mass, the content is preferably 40% by mass or less, more preferably 20% by mass or less, and even more preferably 10% by mass or less. The lower limit can be 0.01% by mass or more, 0.05% by mass or more, 0.1% by mass or more, etc.

[0172] In the present invention, "component (A)" and "active ester curing agents other than component (A)" are collectively referred to simply as "active ester curing agents." The resin composition of the present invention may contain one active ester curing agent, or it may contain two or more active ester curing agents. In one embodiment, the resin composition of the present invention contains one active ester curing agent. That is, in one embodiment, the present invention can exclude resin compositions containing two or more active ester curing agents.

[0173] The preferred and possible ranges for the content of the active ester-based curing agent in the resin composition are the same as the preferred and possible ranges for the content of (A) the aromatic oxycarbonyl compound of the present invention in the resin composition described above.

[0174] The preferred and possible ranges for the content of the epoxy resin curing agent in the resin composition (total content of component (A) and component (D)) are the same as the preferred and possible ranges for the content of (A) the aromatic oxycarbonyl compound of the present invention in the resin composition described above.

[0175] <(E) Thermoplastic resin> The resin composition of the present invention may further contain (E) thermoplastic resin as an optional component.

[0176] Examples of thermoplastic resins include phenoxy resin, polyvinyl acetal resin, polyolefin resin, polybutadiene resin, polyimide resin, polyamideimide resin, polyetherimide resin, polysulfone resin, polyethersulfone resin, polyphenylene ether resin, polycarbonate resin, polyetheretherketone resin, and polyester resin. Among these, phenoxy resin is preferred from the viewpoint of significantly obtaining the effects of the present invention. The phenoxy resin described herein is a component other than epoxy resin. Furthermore, thermoplastic resins may be used individually or in combination of two or more types.

[0177] Examples of phenoxy resins include phenoxy resins having one or more skeletons selected from the group consisting of bisphenol A skeleton, bisphenol F skeleton, bisphenol S skeleton, bisphenolacetophenone skeleton, novolac skeleton, biphenyl skeleton, fluorene skeleton, dicyclopentadiene skeleton, norbornene skeleton, naphthalene skeleton, anthracene skeleton, adamantane skeleton, terpene skeleton, and trimethylcyclohexane skeleton. The terminal end of the phenoxy resin may be any functional group such as a phenolic hydroxyl group or an epoxy group.

[0178] Specific examples of phenoxy resins include "1256" and "4250" (both phenoxy resins containing a bisphenol A skeleton) manufactured by Mitsubishi Chemical Corporation; "YX8100" (phenoxy resin containing a bisphenol S skeleton) manufactured by Mitsubishi Chemical Corporation; "YX6954" (phenoxy resin containing a bisphenol acetophenone skeleton) manufactured by Mitsubishi Chemical Corporation; "FX280" and "FX293" manufactured by Nippon Steel Chemical & Material Co., Ltd.; and "YL6954BH30", "YL7500BH30", "YX6954BH30", "YX7553", "YX7553BH30", "YL7769BH30", "YL6794", "YL7213", "YL7290", "YL7482", and "YL7891BH30" manufactured by Mitsubishi Chemical Corporation.

[0179] Examples of polyvinyl acetal resins include polyvinyl formal resin and polyvinyl butyral resin, with polyvinyl butyral resin being preferred. Specific examples of polyvinyl acetal resins include S-Rec BH series, BX series (e.g., BX-5Z), KS series (e.g., KS-1), BL series, and BM series manufactured by Sekisui Chemical Co., Ltd.

[0180] Examples of polyolefin resins include ethylene-based copolymer resins such as low-density polyethylene, ultra-low-density polyethylene, high-density polyethylene, ethylene-vinyl acetate copolymer, ethylene-ethyl acrylate copolymer, and ethylene-methyl acrylate copolymer; and polyolefin polymers such as polypropylene and ethylene-propylene block copolymer.

[0181] Specific examples of polyimide resins include "Ricacoat SN20" and "Ricacoat PN20" manufactured by Shin Nippon Rika Co., Ltd.

[0182] Specific examples of polyamide-imide resins include "Viromax HR11NN" and "Viromax HR16NN" manufactured by Toyobo Co., Ltd. Other specific examples of polyamide-imide resins include modified polyamide-imides such as "KS9100" and "KS9300" (polysiloxane skeleton-containing polyamide-imide) manufactured by Resonaq Corporation.

[0183] Specific examples of polyethersulfone resins include "PES5003P" manufactured by Sumitomo Chemical Co., Ltd.

[0184] Specific examples of polysulfone resins include Solvay Advanced Polymers' polysulfones "P1700" and "P3500".

[0185] Examples of polyester resins include polyethylene terephthalate resin, polyethylene naphthalate resin, polybutylene terephthalate resin, polybutylene naphthalate resin, polytrimethylene terephthalate resin, polytrimethylene naphthalate resin, and polycyclohexanedimethyl terephthalate resin.

[0186] The weight-average molecular weight (Mw) of the thermoplastic resin is preferably 8,000 or more, more preferably 10,000 or more, particularly preferably 20,000 or more, preferably 70,000 or less, more preferably 60,000 or less, and particularly preferably 50,000 or less, from the viewpoint of significantly obtaining the effects of the present invention.

[0187] When the resin composition of the present invention contains (E) thermoplastic resin, the content of (E) thermoplastic resin in the resin composition may be determined according to the properties required for the resin composition, but when the resin components in the resin composition are taken as 100% by mass, it is preferably 0.1% by mass or more, 1% by mass or more, or 2% by mass or more, more preferably 3% by mass or more, or 4% by mass or more, and even more preferably 5% by mass or more. The upper limit is preferably 30% by mass or less, or 20% by mass or less, more preferably 15% by mass or less, or 10% by mass or less, and even more preferably 9% by mass or less.

[0188] When the resin composition of the present invention contains (E) thermoplastic resin, the content of (E) thermoplastic resin in the resin composition may be determined according to the properties required for the resin composition, but when the nonvolatile components in the resin composition are taken as 100% by mass, it is preferably 0.01% by mass or more, 0.1% by mass or more, or 0.2% by mass or more, more preferably 0.5% by mass or more, or 0.8% by mass or more, and even more preferably 1% by mass or more. The upper limit is preferably 10% by mass or less, or 8% by mass or less, more preferably 6% by mass or less, 5% by mass or less, or 4% by mass or less, and even more preferably 3% by mass or less, 2% by mass or less, or 1.5% by mass or less.

[0189] <(F) Inorganic Filler> The resin composition of the present invention may further contain (F) an inorganic filler as an optional component. By including (F) an inorganic filler, the dielectric loss tangent of the cured product can be further reduced.

[0190] (F) Inorganic compounds can be used as the material for the inorganic filler. (F) Examples of inorganic fillers include silica, alumina, aluminosilicate, 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 is preferred. Examples of silica include amorphous silica, fused silica, crystalline silica, synthetic silica, and hollow silica. Spherical silica is preferred as the shape of the silica. (F) The inorganic filler may be used alone or in combination of two or more types in any ratio.

[0191] (F) Examples of commercially available inorganic fillers include "SP60-05" and "SP507-05" from Nippon Steel Chemical & Material Co., Ltd.; "YC100C", "YA050C", "YA050C-MJE", "YA010C", "SC2500SQ", "SO-C4", "SO-C2", "SO-C1", "SC2300-SVJ", "SC2050-SXF", and "180nmSX-C1" from Admatex Co., Ltd.; "UFP-30", "DAW-03", and "FB-105FD" from Denka Co., Ltd.; "Silfil NSS-3N", "Silfil NSS-4N", and "Silfil NSS-5N" from Tokuyama Corporation; and "Cellspheres" and "MGH-005" from Taiheiyo Cement Corporation.

[0192] (F) The average particle size of the inorganic filler is preferably 10 μm or less, more preferably 5 μm or less, even more preferably 2 μm or less, even more preferably 1 μm or less, and particularly preferably 0.7 μm or less or 0.5 μm or less, from the viewpoint of making the surface of the cured product (insulating layer) low roughness and facilitating the formation of fine wiring. (F) The lower limit of the average particle size of the inorganic filler is not particularly limited, but is preferably 0.01 μm or more, more preferably 0.05 μm or more, even more preferably 0.1 μm or more, and particularly preferably 0.15 μm or more or 0.2 μm or more. (F) The average particle size of the inorganic filler can be measured by the laser diffraction and scattering method based on Mie scattering theory. Specifically, the particle size distribution of the inorganic filler can be created on a volume basis using a laser diffraction scattering particle size distribution analyzer, and the average particle size can be measured by taking the median diameter as the average particle size. A sample can be used in which 100 mg of inorganic filler and 10 g of methyl ethyl ketone are weighed into a vial and dispersed using ultrasound for 10 minutes. The laser diffraction particle size distribution analyzer can use blue or red light wavelengths and can perform measurements using a flow cell method. Examples of laser diffraction particle size distribution analyzers include the "LA-960" manufactured by Horiba, Ltd.

[0193] (F) The specific surface area of ​​the inorganic filler is not particularly limited, but is preferably 0.1 m². ２ / g or more, more preferably 0.5m ２ / g or more, more preferably 1m ２ / g or more or 3m ２ (F) The upper limit of the specific surface area of ​​the inorganic filler is not particularly limited, but preferably 100 m². ２ / g or less, more preferably 70m ２ / g or less, more preferably 50m ２ / g or less, particularly preferably 40m ２ / g or less or 30m ２ The value is less than or equal to / g. The specific surface area of ​​the inorganic filler can be calculated using the BET method by adsorbing nitrogen gas onto the sample surface using a specific surface area measuring device (Macsorb HM-1210, manufactured by Mountec Co., Ltd.) and then using the BET multipoint method.

[0194] (F) The inorganic filler is preferably surface-treated with a surface treatment agent. Surface treatment can improve the moisture resistance and dispersibility of the inorganic filler (F). Examples of surface treatment agents include vinyl-based silane coupling agents such as vinyltrimethoxysilane and vinyltriethoxysilane; epoxy-based silane coupling agents such as 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, and 3-glycidoxypropyltriethoxysilane; and styryl-based silane coupling agents such as p-styryltrimethoxysilane. Coupling agents; methacryl-based silane coupling agents such as 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, and 3-methacryloxypropyltriethoxysilane; acrylic-based silane coupling agents such as 3-acryloxypropyltrimethoxysilane; N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane, N-(2-aminoethyl)-3-aminopropyltrimethoxysilane, 3-amino Amino-based silane coupling agents such as propyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-triethoxysilyl-N-(1,3-dimethylbutylidene)propylamine, N-phenyl-3-aminopropyltrimethoxysilane, N-phenyl-8-aminooctyltrimethoxysilane, N-(vinylbenzyl)-2-aminoethyl-3-aminopropyltrimethoxysilane; isocyanurate-based silane coupling agents such as tris(trimethoxysilylpropyl)isocyanurate; 3 -Ureidopropyltrialkoxysilane and other ureidopropyl silane coupling agents; mercaptopropyl silane coupling agents such as 3-mercaptopropylmethyldimethoxysilane and 3-mercaptopropyltrimethoxysilane; isocyanate silane coupling agents such as 3-isocyanatetopropyltriethoxysilane; acid anhydride silane coupling agents such as 3-trimethoxysilylpropyl succinic anhydride; sulfide silane coupling agents such as bis(triethoxysilylpropyl)tetrasulfide;Examples include silane coupling agents such as methyltrimethoxysilane and phenyltrimethoxysilane, non-silane coupling alkoxysilane compounds, organosilazane compounds, and titanate coupling agents. Furthermore, the surface treatment agent may be used alone or in combination of two or more in any ratio. In one embodiment, (F) the inorganic filler is preferably surface-treated with an amino-based silane coupling agent, and more preferably with N-phenyl-3-aminopropyltrimethoxysilane.

[0195] If the resin composition of the present invention contains (F) an inorganic filler, the content of (F) the inorganic filler is preferably 5% by mass or more or 10% by mass or more, more preferably 20% by mass or more, 30% by mass or more or 40% by mass or more, even more preferably 50% by mass or more, 60% by mass or more, 70% by mass or more or 80% by mass or more, when the nonvolatile components of the resin composition are taken as 100% by mass. The upper limit is preferably 95% by mass or less, more preferably 90% by mass or less, even more preferably 88% by mass or less, and particularly preferably 86% by mass or less.

[0196] <(G) Thermosetting resins other than epoxy resins> The resin composition of the present invention may further contain (G) thermosetting resins other than epoxy resins as an optional component. The other thermosetting resins may be known resins used when forming the insulating layer of circuit boards and the sealing layer of semiconductor chip packages, and examples include benzocyclobutene resin, epoxy acrylate resin, urethane acrylate resin, urethane resin, cyanate resin, polyimide resin, benzoxazine resin, unsaturated polyester resin, melamine resin, and the like.

[0197] If the resin composition of the present invention contains a thermosetting resin other than (G) epoxy resin, the content of component (G) may be appropriately determined within a range that does not impede the effects of the present invention, but when the total resin component in the resin composition is taken as 100% by mass, it is preferably 40% by mass or less, 30% by mass or less, 25% by mass or less, 20% by mass or less, 15% by mass or less, or 10% by mass or less. The lower limit of the content is not particularly limited, and for example, it may be 0.1% by mass or more, 0.5% by mass or more, 1% by mass or more, etc.

[0198] <(H) Radical Polymerizable Resin> The resin composition of the present invention may further contain (H) radical polymerizable resin as an optional component. Component (H) may be used alone or in combination of two or more.

[0199] The type of radical polymerizable resin is not particularly limited, as long as it has one or more (preferably two or more) radical polymerizable unsaturated groups per molecule. Examples of radical polymerizable resins include resins having one or more radical polymerizable unsaturated groups selected from maleimide groups, vinyl groups, allyl groups, styryl groups, vinylphenyl groups, acryloyl groups, methacryloyl groups, fumaroyl groups, and maleoil groups. In particular, from the viewpoint of producing a cured product with outstanding dielectric and mechanical properties, it is preferable to further include one or more radical polymerizable resins selected from maleimide resins, (meth)acrylic resins, and styryl resins. Here, "maleimide resin" means a resin having maleimide groups. "(meth)acrylic resin" means a resin having acryloyl groups or methacryloyl groups. "Styryl resin" means a resin having styryl groups or vinylphenyl groups. Radical polymerizable resins may be used alone or in combination of two or more types.

[0200] The type of maleimide resin is not particularly limited, as long as it has one or more (preferably two or more) maleimide groups (2,5-dihydro-2,5-dioxo-1H-pyrrole-1-yl groups) per molecule. Examples of maleimide resins include: maleimide resins containing a 36-carbon aliphatic skeleton derived from dimeramine, such as "BMI-3000J", "BMI-5000", "BMI-1400", "BMI-1500", "BMI-1700", and "BMI-689" (all manufactured by Designer Molecules Inc.); maleimide resins containing an indan skeleton, as described in the Japan Institute of Invention and Innovation Publication No. 2020-500211; maleimide resins containing an aromatic ring skeleton directly bonded to the nitrogen atom of the maleimide group, such as "MIR-3000-70MT" (manufactured by Nippon Kayaku Co., Ltd.), "BMI-4000" (manufactured by Yamato Kasei Co., Ltd.), and "BMI-80" (manufactured by Kei-I Kasei Co., Ltd.); and others.

[0201] The type of (meth)acrylic resin is not particularly limited as long as it has one or more (preferably two or more) (meth)acryloyl groups in one molecule, and may be a monomer or oligomer. Here, the term "(meth)acryloyl group" is a general term for acryloyl groups and methacryloyl groups. Examples of (meth)acrylic resins include "A-DOG" (manufactured by Shin-Nakamura Chemical Industry Co., Ltd.), "DCP-A" (manufactured by Kyoeisha Chemical Co., Ltd.), "NPDGA", "FM-400", "R-687", "THE-330", "PET-30", and "DPHA" (all manufactured by Nippon Kayaku Co., Ltd.).

[0202] The type of styryl resin is not particularly limited as long as it has one or more (preferably two or more) styryl groups or vinylphenyl groups in one molecule, and may be a monomer or oligomer. Examples of styryl resins include "OPE-2St", "OPE-2St 1200", and "OPE-2St 2200" (all manufactured by Mitsubishi Gas Chemical Co., Ltd.).

[0203] If the resin composition of the present invention contains a (H) radical polymerizable resin, the content of component (H) may be appropriately determined within a range that does not impede the effects of the present invention. When the total resin component in the resin composition is taken as 100% by mass, it is preferably 40% by mass or less, 30% by mass or less, 25% by mass or less, 20% by mass or less, 15% by mass or less, or 10% by mass or less. The lower limit of the content is not particularly limited and may be, for example, 0.1% by mass or more, 0.5% by mass or more, 1% by mass or more.

[0204] <(I) Organic Solvents> The resin composition of the present invention may further contain (I) organic solvents as an optional component. By incorporating (I) organic solvents into the resin composition, a resin composition varnish with appropriate viscosity can be obtained. In the present invention, "resin composition varnish" refers to a resin composition containing (I) organic solvents. That is, "resin composition varnish" is encompassed within "resin composition". (I) organic solvents may be used alone or in combination of two or more types.

[0205] Examples of component (I) include glycol-based organic solvents, glycol ether-based organic solvents, glycol ether ester-based organic solvents, ketone-based organic solvents, ester-based organic solvents, ether-based organic solvents, alcohol-based organic solvents, aliphatic hydrocarbon-based organic solvents, aromatic organic solvents, nitrogen-based organic solvents, sulfur-based organic solvents, halogen-based organic solvents, etc. Examples of nitrogen-based organic solvents include amide-based organic solvents, urea-based organic solvents, nitrile-based organic solvents, etc. From the viewpoint of safety, component (I) is preferably an ester-based organic solvent, a ketone-based organic solvent, a glycol-based organic solvent, a glycol ether-based organic solvent, or a glycol ether ester-based organic solvent, more preferably an ester-based organic solvent or a ketone-based organic solvent, and particularly preferably a ketone-based organic solvent.

[0206] Examples of glycol-based organic solvents include ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, and trimethylene glycol.

[0207] Examples of glycol ether-based organic solvents include cellosolves such as ethylene glycol monomethyl ether (also known as methyl cellosolve), ethylene glycol monoethyl ether (also known as cellosolve), ethylene glycol monopropyl ether (also known as propyl cellosolve), ethylene glycol monobutyl ether (also known as butyl cellosolve), ethylene glycol monoisobutyl ether (also known as isobutyl cellosolve), ethylene glycol mono-tert-butyl ether (also known as tert-butyl cellosolve), and ethylene glycol monohexyl ether; diethylene glycol monomethyl ether (also known as methyl carbitol), diethylene glycol monoethyl ether ( Examples include carbitols such as diethylene glycol monopropyl ether (also known as carbitol), diethylene glycol monobutyl ether (DB) (also known as butyl carbitol); propylene glycol ethers such as propylene glycol monomethyl ether (PGM), propylene glycol monoethyl ether, propylene glycol monopropyl ether, and propylene glycol monobutyl ether; and dipropylene glycol ethers such as dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol monopropyl ether, and dipropylene glycol monobutyl ether.

[0208] Examples of glycol ether ester organic solvents include cellosolve esters such as ethylene glycol monomethyl ether acetate (also known as methyl cellosolve acetate), ethylene glycol monoethyl ether acetate (also known as cellosolve acetate), and ethylene glycol monobutyl ether acetate (also known as butyl cellosolve acetate); carbitol esters such as diethylene glycol monoethyl ether acetate (EDGAc) (also known as carbitol acetate) and diethylene glycol monobutyl ether acetate (also known as butyl carbitol acetate); propylene glycol ether esters such as propylene glycol monomethyl ether acetate (PGMEAc) and propylene glycol monoethyl ether acetate; and dipropylene glycol ether esters such as dipropylene glycol monomethyl ether acetate.

[0209] Examples of ketone-based organic solvents include aliphatic acyclic ketones such as acetone, methyl ethyl ketone (MEK), diethyl ketone, 2-pentanone, methyl isobutyl ketone, 2-hexanone, 2-heptanone (MAK), and diisobutyl ketone; aliphatic cyclic ketones such as cyclopentanone, cyclohexanone (Anone), and 2-methylcyclohexanone; and aromatic ketones such as acetophenone. Methyl ethyl ketone (MEK) or cyclohexanone are preferred. The lower limit of the number of carbon atoms in the ketone-based organic solvent is preferably 2 or more, more preferably 3 or more, and still more preferably 4 or more. The upper limit of the number of carbon atoms in the ketone-based organic solvent is preferably 10 or less, more preferably 8 or less, and still more preferably 6 or less.

[0210] Ester-based organic solvents are organic solvents having an ester structure that do not fall under the category of glycol ether ester-based organic solvents. Examples include fatty acid alkyl esters such as methyl acetate, ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, isobutyl acetate, sec-butyl acetate, tert-butyl acetate, n-pentyl acetate, isopentyl acetate, ethyl propionate, propyl propionate, and isopropyl propionate; alkyl hydroxy acid esters such as methyl lactate, ethyl lactate, and butyl lactate; alkyl keto acid esters such as methyl acetoacetate and ethyl acetoacetate; lactones such as γ-butyrolactone and α-acetyl-γ-butyrolactone; and aromatic esters such as methyl benzoate and ethyl benzoate. Lactones are preferred as ester-based organic solvents. Furthermore, the number of carbon atoms in the ester-based organic solvent is preferably 3 to 9.

[0211] Ether-based organic solvents are organic solvents having an ether structure that do not fall under glycol ether-based organic solvents or glycol ether ester-based organic solvents. Examples include aliphatic acyclic ethers such as dimethyl ether, diethyl ether, methyl ethyl ether, diisopropyl ether, dibutyl ether, methyl tert-butyl ether, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, and triethylene glycol dimethyl ether; aliphatic cyclic ethers such as tetrahydrofuran, 1,4-dioxane, and 1,3-dioxolane; and aromatic ethers such as anisole and phenethole. The number of carbon atoms in ether-based organic solvents is preferably 2 to 9.

[0212] Alcohol-based organic solvents are organic solvents having an alcohol structure that do not fall under the category of glycol-based organic solvents or glycol ether-based organic solvents. Examples include aliphatic acyclic alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butyl alcohol, isobutyl alcohol, sec-butyl alcohol, tert-butyl alcohol, n-pentyl alcohol, isopentyl alcohol, sec-pentyl alcohol, tert-pentyl alcohol, neopentyl alcohol, n-hexyl alcohol, n-heptyl alcohol, isoheptyl alcohol, n-octyl alcohol, and 2-ethylhexyl alcohol; aliphatic cyclic alcohols such as cyclohexanol; and aromatic alcohols such as benzyl alcohol and phenethyl alcohol.

[0213] Examples of aliphatic hydrocarbon organic solvents include n-pentane, n-hexane, 2-methylpentane (also known as isohexane), n-heptane, n-octane, cyclopentane, cyclohexane, methylcyclohexane, ethylcyclohexane, and decalin. The aliphatic hydrocarbon organic solvent preferably has 5 to 10 carbon atoms.

[0214] Examples of aromatic organic solvents include benzene, toluene, o-xylene, m-xylene, p-xylene, ethylbenzene, etc. ６－８ Aromatic hydrocarbons; such as 1,2,3-trimethylbenzene, 1,3,5-trimethylbenzene (also known as mesitylene), 1,2,4-trimethylbenzene, 4-ethyltoluene, 3-ethyltoluene, 2-ethyltoluene, etc. ９ Aromatic hydrocarbons; such as 1,2-diethylbenzene, 1,3-diethylbenzene, 1,4-diethylbenzene, 3-ethyl-o-xylene, 4-ethyl-o-xylene, 2-ethyl-p-xylene, 1,2,3,5-tetramethylbenzene, tetralin, etc. １０ Aromatic hydrocarbons include aromatic heterocyclic compounds such as pyridine, furan, and thiophene. The aromatic organic solvent preferably has 6 to 10 carbon atoms.

[0215] Examples of amide-based organic solvents include aliphatic acyclic amides such as N,N-dimethylacetamide and N,N-dimethylformamide; lactams such as N-methyl-2-pyrrolidone and N-cyclohexyl-2-pyrrolidone; and phosphate amides such as hexamethylphosphoramide. The number of carbon atoms in the amide-based organic solvent is preferably 2 to 10.

[0216] Examples of urea-based organic solvents include tetramethylurea and 1,3-dimethyl-2-imidazolinone.

[0217] Examples of nitrile-based organic solvents include acetonitrile, propionitrile, and benzonitrile. The number of carbon atoms in the nitrile-based organic solvent is preferably 2 to 10.

[0218] Examples of sulfur-based organic solvents include dimethyl sulfoxide.

[0219] Examples of halogenated organic solvents include chloroform, methylene chloride, carbon tetrachloride, and 1,2-dichloroethane. The halogenated organic solvent preferably has 1 to 10 carbon atoms.

[0220] Among these, γ-butyrolactone, methyl ethyl ketone (MEK), cyclopentanone, cyclohexanone, propylene glycol, or propylene glycol monomethyl ether acetate are preferred, methyl ethyl ketone (MEK), cyclohexanone, or γ-butyrolactone are more preferred, and methyl ethyl ketone (MEK) or cyclohexanone are even more preferred.

[0221] When the resin composition of the present invention contains (I) an organic solvent, the content of (I) the organic solvent in the resin composition may be determined according to the required properties and viscosity of the resin composition. However, when the total components in the resin composition are considered as 100% by mass, the content can be, for example, 60% by mass or less, 40% by mass or less, 30% by mass or less, 20% by mass or less, 15% by mass or less, etc. The lower limit can be 0.1% by mass or more, 1% by mass or more, etc. Because the aromatic oxycarbonyl compound of the present invention has excellent solubility in organic solvents, it can be dissolved in organic solvents even when the amount of organic solvent is small.

[0222] <(J) Other Additives> The resin composition of the present invention may further contain (J) other additives. Examples of such additives include: organic fillers such as rubber particles; radical polymerization initiators such as peroxide-based radical polymerization initiators and azo-based radical polymerization initiators; organometallic compounds such as organocopper compounds, organozinc compounds, and organocalt compounds; colorants such as phthalocyanine blue, phthalocyanine green, iodine green, diazo yellow, crystal violet, titanium dioxide, and carbon black; polymerization inhibitors such as hydroquinone, catechol, pyrogallol, and phenothiazine; leveling agents such as silicone-based leveling agents and acrylic polymer-based leveling agents; thickeners such as bentonite and montmorillonite; defoaming agents such as silicone-based defoaming agents, acrylic-based defoaming agents, fluorine-based defoaming agents, and vinyl resin-based defoaming agents; ultraviolet absorbers such as benzotriazole-based ultraviolet absorbers; adhesion improvers such as urea silane; and triazole-based adhesion fertilizers. Adhesion-enhancing agents such as tetrazole-based adhesion enhancers and triazine-based adhesion enhancers; antioxidants such as hindered phenol-based antioxidants; fluorescent whitening agents such as stilbene derivatives; surfactants such as fluorine-based surfactants and silicone-based surfactants; flame retardants such as phosphorus-based flame retardants (e.g., phosphate ester compounds, phosphazene compounds, phosphinic acid compounds, red phosphorus), nitrogen-based flame retardants (e.g., melamine sulfate), halogen-based flame retardants, and inorganic flame retardants (e.g., antimony trioxide); dispersants such as phosphate ester-based dispersants, polyoxyalkylene-based dispersants, acetylene-based dispersants, silicone-based dispersants, anionic dispersants, and cationic dispersants; and stabilizers such as borate-based stabilizers, titanate-based stabilizers, aluminate-based stabilizers, zirconate-based stabilizers, isocyanate-based stabilizers, carboxylic acid-based stabilizers, and carboxylic acid anhydride-based stabilizers. The content of such additives may be determined according to the properties required of the resin composition. Furthermore, components (A) to (I) may have functions such as organic fillers, radical polymerization initiators, organometallic compounds, colorants, polymerization inhibitors, thickeners, defoamers, ultraviolet absorbers, adhesion enhancers, adhesion-improving agents, antioxidants, fluorescent whitening agents, flame retardants, dispersants, and stabilizers. In that case, such components shall be considered as components (A) to (I), rather than component (J).

[0223] The resin composition of the present invention can be prepared by appropriately mixing the necessary components from the above components (A) to (J), and by kneading or mixing them using a kneading means such as a three-roll mill, ball mill, bead mill, or sand mill, or a stirring means such as a super mixer or planetary mixer, as needed.

[0224] <Physical Properties and Applications of the Resin Composition> In one embodiment, the cured product of the resin composition of the present invention exhibits a low relative permittivity (Dk). For example, as described in the [Dielectric Properties] section below, when measured at 5.8 GHz and 23°C, the relative permittivity (Dk) of the cured product of the resin composition of the present invention may be 3.5 or less, 3.4 or less, 3.3 or less, 3.2 or less, 3.1 or less, 3.0 or less, or 2.9 or less. The lower limit is not particularly limited, but may be 1.0 or more, 1.1 or more, 1.5 or more, etc.

[0225] In one embodiment, the cured product of the resin composition of the present invention exhibits a low dielectric loss tangent (Df). For example, as described in the [Dielectric Properties] section below, when measured at 5.8 GHz and 23°C, the dielectric loss tangent (Df) of the cured product of the resin composition of the present invention may be 0.01 or less, 0.008 or less, or 0.006 or less. The lower limit is not particularly limited, but may be 0.0001 or more or 0.001 or more, etc.

[0226] In one embodiment, the cured product of the resin composition of the present invention exhibits high heat resistance. For example, as described in the [Heat Resistance] section below, when measured using a dynamic viscoelasticity measuring device under measurement conditions of a load of 200 mN and a heating rate of 2°C / min, the glass transition temperature (Tg) can be 120°C or higher, 130°C or higher, 140°C or higher, 145°C or higher, 150°C or higher, or 155°C or higher. The upper limit is not particularly limited, but it can be 400°C or lower, 300°C or lower, etc.

[0227] In one embodiment, the cured product of the resin composition of the present invention exhibits high flame retardancy. For example, when a flame retardancy test is conducted in accordance with the UL94 standard, the flame retardancy is preferably "V-1", more preferably "V-0", or better.

[0228] As described above, the resin composition of the present invention can produce a cured product exhibiting excellent flame retardancy, excellent dielectric properties, and heat resistance, achieving the flame retardancy, low transmission loss, and heat resistance required for 5G applications. Therefore, the resin composition of the present invention can be suitably used as a resin composition for forming an insulating layer of a printed wiring board (resin composition for insulating layer of printed wiring board), and more suitably used as a resin composition for forming an interlayer insulating layer of a printed wiring board (resin composition for interlayer insulating layer of printed wiring board). The resin composition of the present invention can also be suitably used when the printed wiring board is a circuit board with embedded components. The resin composition of the present invention can also be suitably used in semiconductor chip packages as a resin composition for a redistribution forming layer as an insulating layer for forming a redistribution layer (resin composition for redistribution forming layer), that is, for forming an insulating layer of a redistribution substrate of a semiconductor chip package (for insulating layer of redistribution substrate). In the present invention, printed wiring boards and redistribution substrates are collectively referred to as "circuit boards," and therefore the resin composition of the present invention can be suitably used as an insulating layer for circuit boards.

[0229] The resin composition of the present invention can also be suitably used as a resin composition for encapsulating semiconductor chips in semiconductor chip packages (resin composition for semiconductor encapsulation).

[0230] The resin composition of the present invention can be used in a wide range of applications where a resin composition is required, such as sheet-like laminated materials like resin sheets and prepregs, solder resists, underfill materials, die bonding materials, hole-filling resins, and component-embedding resins.

[0231] [Sheet-like laminated material (resin sheet, prepreg)] The resin composition of the present invention can be used as is, but it may also be used in the form of a sheet-like laminated material containing the resin composition.

[0232] As sheet-like laminated materials, the following resin sheets and prepregs are preferred.

[0233] In one embodiment, the resin sheet comprises a support and a layer of a resin composition provided on the support (hereinafter simply referred to as the "resin composition layer"), wherein the resin composition layer is formed from the resin composition of the present invention.

[0234] The optimal thickness of the resin composition layer varies depending on the application and may be determined appropriately according to the application. For example, from the viewpoint of thinning printed circuit boards and semiconductor chip packages, the thickness of the resin composition layer is preferably 200 μm or less, more preferably 150 μm or less, 120 μm or less, 100 μm or less, 80 μm or less, 60 μm or less, or 50 μm or less. The lower limit of the thickness of the resin composition layer is not particularly limited, but can usually be 1 μm or more, 5 μm or more, etc.

[0235] Examples of support materials include thermoplastic resin films, metal foils, and release paper, with thermoplastic resin films and metal foils being preferred. Therefore, in one preferred embodiment, the support material is a thermoplastic resin film or a metal foil.

[0236] When using a thermoplastic resin film as a support, examples of thermoplastic resins include polyesters such as polyethylene terephthalate (PET) and polyethylene naphthalate (PEN), acrylics such as polycarbonate (PC) and polymethyl methacrylate (PMMA), cyclic polyolefins, triacetylcellulose (TAC), polyether sulfide (PES), polyether ketones, and polyimides. Among these, polyethylene terephthalate and polyethylene naphthalate are preferred, and inexpensive polyethylene terephthalate is particularly preferred.

[0237] When using a metal foil as a support, examples of metal foils include copper foil and aluminum foil, with copper foil being preferred. As for the copper foil, a foil containing a single metal of copper may be used, or a foil containing an alloy of copper with another metal (for example, tin, chromium, silver, magnesium, nickel, zirconium, silicon, titanium, etc.) may be used. In one embodiment, as the copper foil, a foil made of a single metal of copper may be used, or a foil made of an alloy of copper with another metal (for example, tin, chromium, silver, magnesium, nickel, zirconium, silicon, titanium, etc.) may be used.

[0238] The support may have a matte finish, corona treatment, or antistatic treatment applied to the surface that joins with the resin composition layer. Alternatively, a support with a release layer may be used, which has a release layer on the surface that joins with the resin composition layer. Examples of release agents used in the release layer of the support with a release layer include one or more release agents selected from the group consisting of alkyd resins, polyolefin resins, urethane resins, and silicone resins. Examples of commercially available release agents include "SK-1", "AL-5", and "AL-7" from Lintec Corporation. Furthermore, commercially available support with a release layer may also be used, for example, "Purex" from Toyobo Co., Ltd. and "Unipeel" from Unitika Corporation, which are PET films having a release layer mainly composed of an alkyd resin-based release agent or a polyolefin resin-based release agent.

[0239] The thickness of the support is not particularly limited, but is preferably in the range of 5 μm to 75 μm, and more preferably in the range of 10 μm to 60 μm. When using a support with a release layer, it is preferable that the overall thickness of the support with the release layer is within the above range.

[0240] When using metal foil as a support, a metal foil with a support substrate, which is formed by laminating a peelable support substrate onto a thin metal foil, may be used. In one embodiment, the metal foil with a support substrate includes a support substrate, a release layer provided on the support substrate, and a metal foil provided on the release layer. When using metal foil with a support substrate as a support, the resin composition layer is provided on the metal foil.

[0241] In a metal foil with a support substrate, the material of the support substrate is not particularly limited, but examples include copper foil, aluminum foil, stainless steel foil, titanium foil, copper alloy foil, etc. When copper foil is used as the support substrate, it may be electrolytic copper foil or rolled copper foil. Furthermore, the release layer is not particularly limited as long as it can be peeled off the metal foil from the support substrate, and examples include an alloy layer of elements selected from the group consisting of Cr, Ni, Co, Fe, Mo, Ti, W, and P; an organic coating, etc.

[0242] In a metal foil with a support substrate, the material of the metal foil is preferably, for example, copper foil or copper alloy foil.

[0243] In a metal foil with a support substrate, the thickness of the support substrate is not particularly limited, but is preferably in the range of 10 μm to 150 μm, and more preferably in the range of 10 μm to 100 μm. The thickness of the metal foil may be, for example, in the range of 0.1 μm to 10 μm.

[0244] In one embodiment, the resin sheet may further include any additional layer as needed. Such an additional layer may be, for example, a protective film provided on the side of the resin composition layer that is not bonded to the support (i.e., the side opposite to the support). The thickness of the protective film is not particularly limited, but is, for example, 1 μm to 40 μm. By laminating the protective film, the adhesion of dust and other debris to the surface of the resin composition layer and scratches can be suppressed.

[0245] A resin sheet can be manufactured, for example, by preparing a resin composition varnish by using a liquid resin composition as is or by dissolving the resin composition in an organic solvent, applying this varnish to a support using a die coater or the like, and then drying it to form a resin composition layer.

[0246] Examples of organic solvents include those similar to those described as components of the resin composition in section (I) Organic Solvents. Organic solvents may be used individually or in combination of two or more.

[0247] Drying may be carried out by known methods such as heating or blowing hot air. The drying conditions are not particularly limited, but the resin composition layer should be dried so that the content of the organic solvent in the resin composition layer is 10% by mass or less, preferably 5% by mass or less. Depending on the boiling point of the organic solvent in the resin composition or resin varnish, for example, when using a resin composition or resin varnish containing 10% to 60% by mass of organic solvent, the resin composition layer can be formed by drying at 50°C to 150°C for 3 to 10 minutes.

[0248] The resin sheet can be stored by rolling it up. If the resin sheet has a protective film, it can be used after removing the protective film.

[0249] In one embodiment, the prepreg is formed by impregnating a sheet-like fibrous substrate with the resin composition of the present invention.

[0250] The sheet-like fibrous substrate used for the prepreg is not particularly limited, and commonly used prepreg substrates such as glass cloth, aramid nonwoven fabric, and liquid crystal polymer nonwoven fabric can be used. From the viewpoint of thinning printed circuit boards and semiconductor chip packages, the thickness of the sheet-like fibrous substrate is preferably 50 μm or less, more preferably 40 μm or less, even more preferably 30 μm or less, and particularly preferably 20 μm or less. The lower limit of the thickness of the sheet-like fibrous substrate is not particularly limited, but is usually 10 μm or more.

[0251] Prepregs can be manufactured by known methods such as the hot melt method and the solvent method.

[0252] The thickness of the prepreg can be within the same range as the resin composition layer in the resin sheet described above.

[0253] The sheet-like laminated material of the present invention can be suitably used to form an insulating layer of a printed circuit board (for insulating layers of printed circuit boards), and more suitably used to form an interlayer insulating layer of a printed circuit board (for interlayer insulating layers of printed circuit boards). The sheet-like laminated material of the present invention can also be suitably used to form an insulating layer of a redistribution substrate for a semiconductor chip package (for insulating layers of a redistribution substrate). In other words, the sheet-like laminated material of the present invention can be suitably used as an insulating layer for a circuit board. The sheet-like laminated material of the present invention can also be suitably used to encapsulate a semiconductor chip (for semiconductor encapsulation).

[0254] [Circuit board] An insulating layer of a circuit board can be formed using the resin composition of the present invention. The present invention also provides such a circuit board, that is, a circuit board including an insulating layer having a cured product of the resin composition of the present invention. In one embodiment, it is preferable that the circuit board of the present invention is a circuit board including an insulating layer made of a cured product of the resin composition of the present invention.

[0255] <Printed Wiring Board> In one embodiment, the circuit board of the present invention is a printed wiring board. The printed wiring board of the present invention includes an insulating layer having a cured product of the resin composition of the present invention. In one embodiment, it is preferable that the printed wiring board of the present invention includes an insulating layer made of a cured product of the resin composition of the present invention.

[0256] A printed circuit board can be manufactured, for example, using the above-mentioned resin sheet by a method including the following steps (I) and (II): (I) Laminating the resin sheet onto an inner layer substrate such that the resin composition layer of the resin sheet is bonded to the inner layer substrate; (II) Heat curing the resin composition layer to form an insulating layer.

[0257] In step (I), a resin sheet is laminated onto the inner layer substrate such that the resin composition layer of the resin sheet is bonded to the inner layer substrate. The "inner layer substrate" used in step (I) is a material that will become the substrate of a printed wiring board, and examples include glass epoxy substrates, metal substrates, polyester substrates, polyimide substrates, BT resin substrates, thermosetting polyphenylene ether substrates, etc. The substrate may also have a conductive layer on one or both sides, and this conductive layer may be patterned. An inner layer substrate in which a conductive layer (circuit) is formed on one or both sides of the substrate is sometimes called an "inner layer circuit board". Furthermore, an intermediate product on which an insulating layer and / or a conductive layer is to be formed when manufacturing a printed wiring board is also included in the "inner layer substrate" as defined in this invention. If the printed wiring board is a circuit board with embedded components, an inner layer substrate with embedded components may be used.

[0258] The lamination of the inner layer substrate and the resin sheet can be performed, for example, by heating and pressing the resin sheet onto the inner layer substrate from the support side. Examples of the heating and pressing member used to heat and press the resin sheet onto the inner layer substrate (hereinafter also referred to as the "heat pressing member") include a heated metal plate (such as a SUS end plate) or a metal roll (such as a SUS roll). The heating and pressing member may be pressed directly onto the resin sheet, or it may be pressed via an elastic material such as heat-resistant rubber so that the resin sheet can adequately follow the surface irregularities of the inner layer substrate.

[0259] Lamination of the inner layer substrate and the resin sheet may be carried out by a vacuum lamination method. In the vacuum lamination method, the heat-pressure temperature is preferably in the range of 60°C to 160°C, more preferably in the range of 80°C to 140°C, the heat-pressure pressure is preferably in the range of 0.098 MPa to 1.77 MPa, more preferably in the range of 0.29 MPa to 1.47 MPa, and the heat-pressure time is preferably in the range of 10 seconds to 400 seconds, more preferably in the range of 20 seconds to 300 seconds. Lamination may preferably be carried out under reduced pressure conditions of 26.7 hPa or less.

[0260] Lamination can be performed using a commercially available vacuum laminator. Examples of commercially available vacuum laminators include vacuum pressure laminators manufactured by Meiki Seisakusho Co., Ltd., vacuum applicators manufactured by Nikko Materials Co., Ltd., and batch-type vacuum pressure laminators.

[0261] After lamination, the laminated resin sheets may be smoothed by pressing a heat-sealing member from the support side under normal pressure (atmospheric pressure). The pressing conditions for the smoothing process can be the same as the heat-sealing conditions for lamination. The smoothing process can be performed using a commercially available laminator. Lamination and smoothing may be performed continuously using the commercially available vacuum laminator mentioned above.

[0262] The support may be removed between steps (I) and (II), or after step (II). If a metal foil is used as the support, the conductive layer may be formed using the metal foil without peeling off the support. If a metal foil with a support substrate is used as the support, the support substrate (and release layer) should be peeled off. Then, the conductive layer can be formed using the metal foil.

[0263] In step (II), the resin composition layer is heat-cured to form an insulating layer having a cured resin composition. In one embodiment, it is preferable in step (II) to heat-cur the resin composition layer to form an insulating layer consisting of a cured resin composition. The curing conditions for the resin composition layer are not particularly limited, and conditions commonly used when forming an insulating layer for a printed circuit board may be used.

[0264] For example, the thermal curing conditions for the resin composition layer vary depending on the type of resin composition, but in one embodiment, the curing temperature is preferably 120°C to 250°C, more preferably 150°C to 240°C, and even more preferably 180°C to 230°C. The curing time can be preferably 5 minutes to 240 minutes, more preferably 10 minutes to 150 minutes, and even more preferably 15 minutes to 120 minutes.

[0265] Prior to thermal curing the resin composition layer, the resin composition layer may be preheated at a temperature lower than the curing temperature. For example, prior to thermal curing the resin composition layer, the resin composition layer may be preheated at a temperature of 50°C to 120°C, preferably 60°C to 115°C, more preferably 70°C to 110°C for 5 minutes or more, preferably 5 minutes to 150 minutes, more preferably 15 minutes to 120 minutes, and even more preferably 15 minutes to 100 minutes.

[0266] In manufacturing printed circuit boards, the following steps may be further performed: (III) drilling holes in the insulating layer, (IV) roughening the insulating layer, and (V) forming the conductor layer. These steps (III) to (V) may be carried out according to various methods known to those skilled in the art that are used in the manufacture of printed circuit boards. If the support is removed after step (II), the removal of the support may be carried out between steps (II) and (III), between steps (III) and (IV), or between steps (IV) and (V). Furthermore, if necessary, the formation of the insulating layer and the conductor layer in steps (I) to (V) may be repeated to form a multilayer circuit board.

[0267] In other embodiments, the printed circuit board of the present invention can be manufactured using the prepreg described above. The manufacturing method is basically the same as when a resin sheet is used.

[0268] Step (III) is a process of drilling holes in the insulating layer, thereby forming holes such as via holes and through holes in the insulating layer. Step (III) may be carried out using, for example, a drill, laser, plasma, etc., depending on the composition of the resin composition used to form the insulating layer. The dimensions and shape of the holes may be appropriately determined according to the design of the printed circuit board.

[0269] Step (IV) is a process for roughening the insulating layer. Typically, smear removal (desmear) is also performed in this step (IV). The procedure and conditions for the roughening process are not particularly limited, and known procedures and conditions commonly used when forming the insulating layer of a printed circuit board can be adopted. For example, the insulating layer can be roughened by performing swelling treatment with a swelling solution, roughening treatment with an oxidizing agent, and neutralization treatment with a neutralizing solution in this order.

[0270] The swelling solution used for the roughening treatment is not particularly limited, but examples include alkaline solutions and surfactant solutions, and is preferably an alkaline solution, with sodium hydroxide solution and potassium hydroxide solution being more preferred. Examples of commercially available swelling solutions include "Swelling Dip Securigans P" and "Swelling Dip Securigans SBU" manufactured by Atotec Japan. The swelling treatment with the swelling solution is not particularly limited, but can be carried out, for example, by immersing the insulating layer in a swelling solution at 30°C to 90°C for 1 to 20 minutes. From the viewpoint of suppressing the swelling of the resin of the insulating layer to an appropriate level, it is preferable to immerse the insulating layer in a swelling solution at 40°C to 80°C for 5 to 15 minutes.

[0271] The oxidizing agent used for the roughening treatment is not particularly limited, but examples include an alkaline permanganate solution obtained by dissolving potassium permanganate or sodium permanganate in an aqueous solution of sodium hydroxide. The roughening treatment with an oxidizing agent such as an alkaline permanganate solution is preferably carried out by immersing the insulating layer in an oxidizing agent solution heated to 60°C to 100°C for 10 to 30 minutes. Furthermore, the concentration of permanganate in the alkaline permanganate solution is preferably 5% to 10% by mass. Examples of commercially available oxidizing agents include alkaline permanganate solutions such as "Concentrate Compact CP," "Concentrate Compact P," and "Dosing Solution Securigans P" manufactured by Attec Japan.

[0272] Furthermore, an acidic aqueous solution is preferred as the neutralizing solution used in the roughening treatment. Examples of commercially available products include "Reduction Solution Securigant P" manufactured by Attec Japan Co., Ltd.

[0273] The neutralization treatment can be carried out by immersing the treated surface, which has been roughened with an oxidizing agent, in a neutralization solution at 30°C to 80°C for 5 to 30 minutes. From the viewpoint of workability, it is preferable to immerse the object that has been roughened with an oxidizing agent in a neutralization solution at 40°C to 70°C for 5 to 20 minutes.

[0274] Step (V) is a step of forming a conductive layer, in which a conductive layer is formed on an insulating layer. The conductive material used for the conductive layer is not particularly limited. In a preferred embodiment, the conductive layer contains one or more metals selected from the group consisting of gold, platinum, palladium, silver, copper, aluminum, cobalt, chromium, zinc, nickel, titanium, tungsten, iron, tin, and indium. The conductive layer may be a single-metal layer or an alloy layer, and examples of alloy layers include layers formed from alloys of two or more metals selected from the above group (e.g., nickel-chromium alloy, copper-nickel alloy, and copper-titanium alloy). In particular, from the viewpoint of versatility in conductor layer formation, cost, and ease of patterning, single metal layers of chromium, nickel, titanium, aluminum, zinc, gold, palladium, silver, or copper, or alloy layers of nickel-chromium alloy, copper-nickel alloy, or copper-titanium alloy are preferred, single metal layers of chromium, nickel, titanium, aluminum, zinc, gold, palladium, silver, or copper, or alloy layers of nickel-chromium alloy are more preferred, and single metal layers of copper are even more preferred.

[0275] The conductive layer may be a single layer or a multilayer structure in which two or more single-metal layers or alloy layers containing different types of metals or alloys are laminated. In one embodiment, the conductive layer may be a single layer or a multilayer structure in which two or more single-metal layers or alloy layers made of different types of metals or alloys are laminated. When the conductive layer is a multilayer structure, the layer in contact with the insulating layer is preferably a single-metal layer of chromium, zinc, or titanium, or an alloy layer of nickel-chromium alloy.

[0276] The thickness of the conductor layer depends on the desired printed circuit board design, but is generally 3 μm to 35 μm, preferably 5 μm to 30 μm.

[0277] In one embodiment, the conductor layer may be formed by plating. For example, a conductor layer having a desired wiring pattern can be formed by plating the surface of the insulating layer using conventionally known techniques such as the semi-additive method or the fully additive method. From the viewpoint of ease of manufacture, it is preferable to form it by the semi-additive method. An example of forming the conductor layer by the semi-additive method is shown below.

[0278] First, a plating seed layer is formed on the surface of the insulating layer by electroless plating. Next, a mask pattern is formed on the formed plating seed layer, exposing a portion of the plating seed layer corresponding to the desired wiring pattern. After forming a metal layer on the exposed plating seed layer by electroplating, the mask pattern is removed. Then, the unnecessary plating seed layer can be removed by etching or other means to form a conductor layer having the desired wiring pattern.

[0279] In other embodiments, the conductor layer may be formed using metal foil. When forming the conductor layer using metal foil, step (V) is preferably performed between steps (I) and (II). For example, after step (I), the support is removed and the metal foil is laminated onto the surface of the exposed resin composition layer. The lamination of the resin composition layer and the metal foil may be carried out by a vacuum lamination method. The lamination conditions may be the same as those described for step (I). Next, step (II) is performed to form an insulating layer. Subsequently, the metal foil on the insulating layer can be used to form a conductor layer having a desired wiring pattern by conventional known techniques such as the subtractive method or the modified semi-additive method.

[0280] Metal foils can be manufactured by known methods such as electrolysis and rolling. Examples of commercially available metal foils include "HLP foil" and "JXUT-III foil" from JX Metals Corporation, and "3EC-III foil" and "TP-III foil" from Mitsui Mining & Smelting Co., Ltd.

[0281] Alternatively, as mentioned above, if a metal foil or a metal foil with a support substrate is used as the support for the resin sheet, the conductive layer may be formed using the metal foil.

[0282] <Redistribution board for semiconductor chip packages> In one embodiment, the circuit board of the present invention is a redistribution board for semiconductor chip packages. The following description will be based on the manufacturing method of the semiconductor chip package.

[0283] [Semiconductor Chip Package] The semiconductor chip package of the present invention includes a sealing layer having a cured product of the resin composition of the present invention. In one embodiment, it is preferable that the semiconductor chip package of the present invention includes a sealing layer made of a cured product of the resin composition of the present invention. The semiconductor chip package of the present invention may also include an insulating layer (redistribution forming layer) of a redistribution substrate having a cured product of the resin composition of the present invention, as described above. In one embodiment, the semiconductor chip package of the present invention may also include an insulating layer (redistribution forming layer) of a redistribution substrate making of a cured product of the resin composition of the present invention, as described above.

[0284] A semiconductor chip package can be manufactured, for example, using the resin composition and resin sheet of the present invention by a method including the following steps (1) to (6). The resin composition and resin sheet of the present invention may be used to form the sealing layer in step (3) or the redistribution layer in step (5). An example of forming a sealing layer and a redistribution layer using the resin composition and resin sheet is shown below, but the techniques for forming sealing layers and redistribution layers of semiconductor chip packages are well known, and those skilled in the art can manufacture a semiconductor chip package using the resin composition and resin sheet of the present invention in accordance with known techniques. (1) A step of laminating a temporary fixing film onto a substrate, (2) A step of temporarily fixing a semiconductor chip onto the temporary fixing film, (3) A step of forming a sealing layer on the semiconductor chip, (4) A step of peeling the substrate and temporary fixing film from the semiconductor chip, (5) A step of forming a redistribution layer as an insulating layer on the surface of the semiconductor chip from which the substrate and temporary fixing film have been peeled, and (6) A step of forming a redistribution layer as a conductive layer on the redistribution layer

[0285] <Step (1)> The material used for the substrate is not particularly limited. Examples of substrates include silicon wafers; glass wafers; glass substrates; metal substrates such as copper, titanium, stainless steel, and cold-rolled steel sheets (SPCC); substrates made by impregnating glass fibers with epoxy resin and heat-curing treatment (e.g., FR-4 substrates); and bismaleimidotriazine resin (BT resin) substrates. In one embodiment, the bismaleimidotriazine resin (BT resin) substrate is a substrate made of bismaleimidotriazine resin (BT resin).

[0286] The temporary fixing film is not limited in material as long as it can be peeled off from the semiconductor chip in step (4) and temporarily fix the semiconductor chip. Commercially available temporary fixing films can be used. Examples of commercially available products include Riva Alpha manufactured by Nitto Denko Corporation.

[0287] <Step (2)> Temporary fixing of semiconductor chips can be performed using known equipment such as a flip-chip bonder or die bonder. The layout and number of semiconductor chips can be appropriately set according to the shape and size of the temporary fixing film, the number of semiconductor chip packages to be produced, etc. For example, they can be temporarily fixed in a matrix arrangement of multiple rows and multiple columns.

[0288] <Step (3)> The resin composition layer of the resin sheet of the present invention is laminated onto a semiconductor chip, or the resin composition of the present invention is applied onto a semiconductor chip and cured (e.g., by heat curing) to form a sealing layer.

[0289] For example, lamination of a semiconductor chip and a resin sheet can be performed by removing the protective film from the resin sheet and then heating and pressing the resin sheet onto the semiconductor chip from the support side. Examples of the heating and pressing member used to heat and press the resin sheet onto the semiconductor chip (hereinafter also referred to as the "heating and pressing member") include a heated metal plate (such as a SUS end plate) or a metal roll (such as a SUS roll). It is preferable to press the resin sheet via an elastic material such as heat-resistant rubber, rather than directly pressing the heating and pressing member onto the resin sheet, so that the resin sheet can adequately follow the surface irregularities of the semiconductor chip. Lamination of the semiconductor chip and the resin sheet may also be carried out by a vacuum lamination method, and the lamination conditions are the same as those described in relation to the manufacturing method of printed circuit boards, and the preferred range is also the same.

[0290] After lamination, the resin composition is heat-cured to form a sealing layer. The heat-curing conditions are the same as those described in relation to the manufacturing method of printed circuit boards.

[0291] The resin sheet support may be peeled off after the resin sheet has been laminated onto the semiconductor chip and heat-cured, or the support may be peeled off before the resin sheet has been laminated onto the semiconductor chip.

[0292] When applying the resin composition of the present invention to form a sealing layer, the application conditions are the same as those for forming the resin composition layer described in relation to the resin sheet of the present invention, and the preferred ranges are also the same.

[0293] <Step (4)> The method for peeling off the substrate and the temporary fixing film can be appropriately changed depending on the material of the temporary fixing film, etc. Examples include a method of peeling off the temporary fixing film by heating and foaming (or expanding) it, and a method of peeling off the temporary fixing film by irradiating it with ultraviolet light from the substrate side to reduce the adhesive strength of the temporary fixing film.

[0294] In a method of peeling off a temporary fixing film by heating and foaming (or expanding) it, the heating conditions are typically 100 to 250°C for 1 to 90 seconds or 5 to 15 minutes. Furthermore, in a method of peeling off a temporary fixing film by irradiating it with ultraviolet light from the substrate side to reduce its adhesive strength, the amount of ultraviolet light irradiated is typically 10 mJ / cm². ２ ~1000mJ / cm２ That is the case.

[0295] <Step (5)> The material used to form the redistribution layer (insulating layer) is not particularly limited as long as it has insulating properties when the redistribution layer (insulating layer) is formed. From the viewpoint of ease of manufacturing semiconductor chip packages, UV-curable resins and thermosetting resins are preferred. The redistribution layer may also be formed using the resin composition or resin sheet of the present invention.

[0296] After forming the redistribution layer, via holes may be formed in the redistribution layer to interlayer connect the semiconductor chip with the conductor layer described later. The via holes may be formed by known methods depending on the material of the redistribution layer.

[0297] <Step (6)> The formation of the conductor layer on the rewiring layer may be carried out in the same manner as in step (V) described in relation to the manufacturing method of a printed circuit board. Alternatively, steps (5) and (6) may be repeated to alternately stack the conductor layer (rewiring layer) and the rewiring layer (insulating layer) (build-up).

[0298] In manufacturing a semiconductor chip package, the following steps may be further performed: (7) forming a solder resist layer on a conductor layer (redistribution layer); (8) forming bumps; and (9) dicing multiple semiconductor chip packages into individual semiconductor chip packages. These steps may be carried out in accordance with various methods known to those skilled in the art for the manufacture of semiconductor chip packages.

[0299] By forming a sealing layer and a redistribution layer using the resin composition and resin sheet of the present invention, which yield a cured product exhibiting excellent dielectric properties, it is possible to realize a semiconductor chip package with extremely low transmission loss, regardless of whether the semiconductor chip package is a fan-in type package or a fan-out type package. In one embodiment, the semiconductor chip package of the present invention is a fan-out type package. The resin composition and resin sheet of the present invention can be applied to fan-out type panel-level packages (FO-PLP) and fan-out type wafer-level packages (FO-WLP). In one embodiment, the semiconductor chip package of the present invention is a fan-out type panel-level package (FOPLP). In another embodiment, the semiconductor chip package of the present invention is a fan-out type wafer-level package (FOWLP).

[0300] [Semiconductor Device] The semiconductor device of the present invention includes a layer having a cured product of the resin composition of the present invention, and includes a circuit board or semiconductor chip package of the present invention. In one embodiment, the semiconductor device of the present invention preferably includes a layer made of a cured product of the resin composition of the present invention.

[0301] Examples of semiconductor devices include various types of semiconductor devices used in electrical products (e.g., computers, mobile phones, digital cameras, and televisions) and vehicles (e.g., motorcycles, automobiles, trains, ships, and aircraft).

[0302] The present invention will be described in more detail below using examples, but the present invention is not limited to these examples. In the following description, unless otherwise specified, "parts" and "%" mean "parts by mass" and "% by mass," respectively.

[0303] <Example 1: Synthesis of Aromatic Oxycarbonyl Compound (1)>

[0304] In a four-necked round-bottom flask equipped with a stirrer, thermometer, and condenser, 31.03 g (0.1 mol, manufactured by Tokyo Chemical Industry Co., Ltd.) of 2,5-dihydroxyphenyl(diphenyl)phosphine oxide, 40.60 g (0.2 mol, manufactured by Tokyo Chemical Industry Co., Ltd.) of isophthalic acid chloride, 34.04 g (0.2 mol, manufactured by Tokyo Chemical Industry Co., Ltd.) of 2-phenylphenol, and 246 g of toluene were charged in a composition ratio such that n=1 and the active ester group equivalent is 228 g / eq. in the theoretical structure shown in formula (1a) above. The mixture was stirred and dissolved while blowing in nitrogen gas. While cooling the solution to a temperature of 30°C or lower, 42.50 g (0.42 mol, manufactured by Junsei Chemical Co., Ltd.) of triethylamine was added dropwise over 1 hour. The reaction solution was then heated to 60°C and stirred at 60°C for 6 hours.

[0305] Subsequently, 82 g of distilled water was added and the mixture was allowed to stand before separation, and the lower layer of by-product amine salt solution was discarded. The upper layer was then purified by washing twice with the same amount of distilled water, and then heated to perform azeotropic dehydration. The resulting solution was microfiltered to remove impurities, and then toluene was distilled under reduced pressure at a maximum temperature of 200°C to obtain 75.32 g of solids.

[0306] From the GPC and IR analysis results, it was confirmed that the obtained solid material has the target molecular structure, i.e., the structure of a phosphorus-containing aromatic oxycarbonyl compound relating to the theoretical structure shown in formula (1a) above. The obtained aromatic oxycarbonyl compound is referred to as "aromatic oxycarbonyl compound (1)". Figure 1 shows the GPC analysis results of aromatic oxycarbonyl compound (1), and Figure 2 shows the IR analysis results of aromatic oxycarbonyl compound (1).

[0307] (GPC measurement conditions) Measurement device: Tosoh Corporation "HLC-8420GPC" Column: Tosoh Corporation Guard column "HXL-L" + Tosoh Corporation "TSK-GEL SuperHZ2000" + Tosoh Corporation "TSK-GEL SuperHZ2000" + Tosoh Corporation "TSK-GEL SuperHZ3000" + Tosoh Corporation "TSK-GEL SuperHZ4000" Detector: RI (differential refractometer) Data processing: Tosoh Corporation "GPC workstation EcoSEC-WorkStation" Column temperature: 40°C Developing solvent: Tetrahydrofuran Flow rate: 0.35 mL / min Standard: In accordance with the measurement manual for the "GPC workstation EcoSEC-WorkStation" mentioned above, the following monodisperse polystyrene with known molecular weight was used. TSKgel A-500, A-1000, A-2500, A-5000, F-1, F-2, F-4, F-10, F-40, F-80 (manufactured by Tosoh Corporation) Sample: 10 μL of tetrahydrofuran solution (0.5% by mass in terms of resin solids) filtered through a microfilter.

[0308] (IR measurement conditions) Measurement device: JASCO Corporation "FT / IR-4600"

[0309] <Example 2: Synthesis of Aromatic Oxycarbonyl Compound (2)>

[0310] In a four-necked round-bottom flask equipped with a stirrer, thermometer, and condenser, 62.06 g (0.2 mol, manufactured by Tokyo Chemical Industry Co., Ltd.) of 2,5-dihydroxyphenyl(diphenyl)phosphine oxide, 60.91 g (0.3 mol, manufactured by Tokyo Chemical Industry Co., Ltd.) of isophthalic acid chloride, 34.04 g (0.2 mol, manufactured by Tokyo Chemical Industry Co., Ltd.) of 2-phenylphenol, and 366 g of toluene were charged in a composition ratio such that, in the theoretical structure shown in formula (2a) above, n=2 and the equivalent amount of active ester groups is 225 g / eq., and the mixture was stirred and dissolved while blowing in nitrogen gas. While cooling the solution to a temperature of 30°C or lower, 63.75 g (0.63 mol, manufactured by Junsei Chemical Co., Ltd.) of triethylamine was added dropwise over 1 hour, and then the reaction solution was heated to 60°C and stirred at 60°C for 6 hours.

[0311] Subsequently, 122 g of distilled water was added and the mixture was allowed to stand before separation, and the lower layer of by-product amine salt solution was discarded. The upper layer was then purified by washing twice with the same amount of distilled water, and then heated to azeotropic dehydration. The resulting solution was microfiltered to remove impurities, and then toluene was distilled under reduced pressure at a maximum temperature of 200°C to obtain 107 g of solids.

[0312] From the GPC and IR analysis results, it was confirmed that the obtained solid material has the target molecular structure, i.e., the structure of a phosphorus-containing aromatic oxycarbonyl compound relating to the theoretical structure shown in formula (2a) above. The obtained aromatic oxycarbonyl compound is referred to as "aromatic oxycarbonyl compound (2)". Figure 3 shows the GPC analysis results of aromatic oxycarbonyl compound (2), and Figure 4 shows the IR analysis results of aromatic oxycarbonyl compound (2).

[0313] <Example 3: Synthesis of Aromatic Oxycarbonyl Compound (3)>

[0314] In a four-necked round-bottom flask equipped with a stirrer, thermometer, and condenser, 62.06 g (0.2 mol, manufactured by Tokyo Chemical Industry Co., Ltd.) of 2,5-dihydroxyphenyl(diphenyl)phosphine oxide, 50.76 g (0.25 mol, manufactured by Tokyo Chemical Industry Co., Ltd.) of isophthalic acid chloride, 17.02 g (0.1 mol, manufactured by Tokyo Chemical Industry Co., Ltd.) of 2-phenylphenol, and 303 g of toluene were charged in a composition ratio such that, in the theoretical structure shown in formula (3a) above, n=4 and the equivalent amount of active ester groups is 223 g / eq., and the mixture was stirred and dissolved while blowing in nitrogen gas. While cooling the solution to a temperature of 30°C or lower, 53.12 g (0.525 mol, manufactured by Junsei Chemical Co., Ltd.) of triethylamine was added dropwise over 1 hour, and then the reaction solution was heated to 60°C and stirred at 60°C for 6 hours.

[0315] Subsequently, 101 g of distilled water was added and the mixture was allowed to stand before separation, and the lower layer of by-product amine salt solution was discarded. The upper layer was then purified by washing twice with the addition of the same amount of distilled water, and then heated to perform azeotropic dehydration. The resulting solution was microfiltered to remove impurities, and then toluene was distilled under reduced pressure at a maximum temperature of 200°C to obtain 90 g of solids.

[0316] From the GPC and IR analysis results, it was confirmed that the obtained solid material has the target molecular structure, i.e., the structure of a phosphorus-containing aromatic oxycarbonyl compound relating to the theoretical structure shown in formula (3a) above. The obtained aromatic oxycarbonyl compound is referred to as "aromatic oxycarbonyl compound (3)". Figure 5 shows the GPC analysis results of aromatic oxycarbonyl compound (3), and Figure 6 shows the IR analysis results of aromatic oxycarbonyl compound (3).

[0317] <Example 4: Synthesis of Aromatic Oxycarbonyl Compound (4)>

[0318] In the theoretical structure shown in formula (4a) above, n=1 and the composition ratio such that the equivalent amount of the active ester group is 228 g / eq., 71 g of solid was obtained in the same manner as in Example 1, except that 34.04 g (0.2 mol, manufactured by Tokyo Chemical Industry Co., Ltd.) of 4-phenylphenol was used instead of 34.04 g (0.2 mol, manufactured by Tokyo Chemical Industry Co., Ltd.) in Example 1.

[0319] From the GPC and IR analysis results, it was confirmed that the obtained solid material has the target molecular structure, i.e., the structure of a phosphorus-containing aromatic oxycarbonyl compound relating to the theoretical structure shown in formula (4a) above. The obtained aromatic oxycarbonyl compound is referred to as "aromatic oxycarbonyl compound (4)". Figure 7 shows the GPC analysis results of aromatic oxycarbonyl compound (4), and Figure 8 shows the IR analysis results of aromatic oxycarbonyl compound (4).

[0320] <Example 5: Synthesis of Aromatic Oxycarbonyl Compound (5)>

[0321] In the theoretical structure shown in formula (5a) above, n=1, and the composition ratio such that the equivalent of the active ester group is 252 g / eq., 79 g of solid was obtained in the same manner as in Example 1, except that 43.48 g of styrene-modified phenol "SP-F" (hydroxyl value 258 mg KOH / g, manufactured by Sanko Co., Ltd.) was used instead of 34.04 g of 2-phenylphenol (0.2 mol, manufactured by Tokyo Chemical Industry Co., Ltd.).

[0322] From the GPC and IR analysis results, it was confirmed that the obtained solid material has the target molecular structure, i.e., the structure of a phosphorus-containing aromatic oxycarbonyl compound relating to the theoretical structure shown in formula (5a) above. The obtained aromatic oxycarbonyl compound is referred to as "aromatic oxycarbonyl compound (5)". Figure 9 shows the GPC analysis results of aromatic oxycarbonyl compound (5), and Figure 10 shows the IR analysis results of aromatic oxycarbonyl compound (5).

[0323] <Example 6: Synthesis of Aromatic Oxycarbonyl Compound (6)> <<Synthesis of Aromatic Monohydroxy Compound (1)>>

[0324] In a 1-liter four-necked round-bottom flask equipped with a stirrer, thermometer, and condenser, 144.0 g (1.0 mol, manufactured by Tokyo Chemical Industry Co., Ltd.), 104.0 g (1.0 mol, manufactured by Tokyo Chemical Industry Co., Ltd.), 2.5 g (manufactured by Tokyo Chemical Industry Co., Ltd.) of p-toluenesulfonic acid monohydrate as an acid catalyst, and 250 g of toluene as a reaction solvent were charged in a composition ratio such that the m value in the theoretical structural formula is 1.0 in the theoretical structure described above. The mixture was then heated to 100°C while taking care to avoid exothermic reaction. The reaction was then carried out at 100°C for 4 hours. Next, the temperature was lowered to 60°C, and 250 g of toluene, 300 g of distilled water, and an appropriate amount of 48% sodium hydroxide aqueous solution for neutralization were added and separated by standing, and the lower by-product saline layer was discarded. The upper layer was then purified by washing twice with the addition of the same amount of distilled water, and then heated to perform azeotropic dehydration. The obtained solution was microfiltered to remove impurities, and then toluene was removed by vacuum distillation at a maximum temperature of 120°C to obtain 232 g of solids.

[0325] The hydroxyl group equivalent of the solid was measured according to the measurement method described below, and a value of 244 g / eq. (theoretical value 248 g / eq.) was obtained. Furthermore, in the mass spectrum (negative ion mode) obtained according to the measurement method described below, spectral peaks corresponding to m=0 isomer (m / z=144), m=1 isomer (m / z=248), and m=2 isomer (m / z=352) were detected. From these analytical data, it was confirmed that the obtained solid had the target molecular structure, i.e., the structure of aromatic monohydroxy compound (1) related to the theoretical structure described above.

[0326] (Method for measuring hydroxyl group equivalent) In accordance with JIS-K0070, the hydroxyl groups in the aromatic monohydroxy compound were acetylated with acetic anhydride and pyridine, followed by hydrolysis, and the hydroxyl group equivalent was quantified by back titration of the remaining acetic acid.

[0327] (Mass Spectrum Measurement Conditions) The sample was diluted to 1 mg / mL with THF, and LC / MS was measured under the following conditions. HPLC: ACQUITY UPLC (Waters Japan Ltd.) MS: SQ Detector 2 (Waters Japan Ltd.) Column: ACQUITY UPLC BEH C8 1.7 μm, 2.1 mm × 50 mm (Waters Japan Ltd.) Mobile phase A: 2 mmol / L ammonium acetate aqueous solution Mobile phase B: 2-propanol / THF (80:20) Mobile phase mixing time and mixing ratio (A%): 0 min (50%) → 5 min (5%) → 12 min (5%) → 12.1 min (50%) → 14 min (50%) Flow rate: 0.25 mL / min Analysis time: 14 min Column temperature: 40°C Ion mode: ESI (Electron Spray Ionization) Negative ion polarity: Positive detection mode or Negative detection mode Solvent removal gas flow rate: 700 L / hr, 250°C Cone gas: 70 L / hr Ion source heater: 150°C

[0328] <<Synthesis of Aromatic Oxycarbonyl Compounds (6)>>

[0329] In the theoretical structure shown in formula (6a) above, n=1 and the equivalent of the active ester group is 267 g / eq., and in the same manner as in Example 1, 49.66 g (0.2 mol) of aromatic monohydroxy compound (1) was used instead of 34.04 g (0.2 mol, manufactured by Tokyo Chemical Industry Co., Ltd.) to obtain 84 g of solid matter.

[0330] From the GPC and IR analysis results, it was confirmed that the obtained solid material has the target molecular structure, i.e., the structure of a phosphorus-containing aromatic oxycarbonyl compound relating to the theoretical structure shown in formula (6a) above. The obtained aromatic oxycarbonyl compound is referred to as "aromatic oxycarbonyl compound (6)". Figure 11 shows the GPC analysis results of aromatic oxycarbonyl compound (6), and Figure 12 shows the IR analysis results of aromatic oxycarbonyl compound (6).

[0331] <Example 7: Synthesis of Aromatic Oxycarbonyl Compound (7)> ​​<<Synthesis of Aromatic Monohydroxy Compound (2)>>

[0332] In the theoretical structure shown in the above formula, 270 g of solids was obtained in the same manner as the synthesis of aromatic monohydroxy compound (1) in Example 6, except that 176.6 g (1.0 mol, manufactured by Tokyo Chemical Industry Co., Ltd.) was used instead of 104.0 g (1.0 mol, manufactured by Tokyo Chemical Industry Co., Ltd.) in the synthesis of aromatic monohydroxy compound (1) in Example 6, to obtain a composition ratio such that the m value is 1.0.

[0333] The hydroxyl group equivalent of the solid was 282 g / eq. (theoretical value 284 g / eq.), and in the mass spectrum (negative ion mode), spectral peaks corresponding to m=0 isomer (m / z=144), m=1 isomer (m / z=284), and m=2 isomer (m / z=424) were detected. From these analytical data, it was confirmed that the obtained solid had the target molecular structure, i.e., the structure of aromatic monohydroxy compound (2) related to the theoretical structure described above.

[0334] <<Synthesis of Aromatic Oxycarbonyl Compounds (7)>>

[0335] In the theoretical structure shown in formula (7a) above, n=1 and the equivalent of the active ester group is 284 g / eq., and in the same manner as in Example 1, 56.87 g (0.2 mol) of aromatic monohydroxy compound (2) was used instead of 34.04 g (0.2 mol, manufactured by Tokyo Chemical Industry Co., Ltd.) to obtain a composition ratio such that n=1 and the equivalent of the active ester group is 284 g / eq., to obtain a solid of 91 g in the same manner as in Example 1.

[0336] From the GPC and IR analysis results, it was confirmed that the obtained solid material has the target molecular structure, i.e., the structure of a phosphorus-containing aromatic oxycarbonyl compound relating to the theoretical structure shown in formula (7a) above. The obtained aromatic oxycarbonyl compound is referred to as "aromatic oxycarbonyl compound (7)". Figure 13 shows the GPC analysis results of aromatic oxycarbonyl compound (7), and Figure 14 shows the IR analysis results of aromatic oxycarbonyl compound (7).

[0337] <Comparative Example 1: Synthesis of Aromatic Oxycarbonyl Compounds (C1)>

[0338] In the theoretical structure shown in formula (1c) above, n=2 and the active ester group equivalent is 217 g / eq. In Example 2, 102 g of solid was obtained in the same manner as in Example 2, except that 28.83 g (0.2 mol) of 1-naphthol was used instead of 34.04 g (0.2 mol, manufactured by Tokyo Chemical Industry Co., Ltd.) in the composition ratio such that n=2 and the active ester group equivalent is 217 g / eq.

[0339] From the GPC and IR analysis results, it was confirmed that the obtained solid material has the target molecular structure, i.e., the structure of a phosphorus-containing aromatic oxycarbonyl compound relating to the theoretical structure shown in formula (1c) above. The obtained aromatic oxycarbonyl compound is referred to as "aromatic oxycarbonyl compound (C1)". Figure 15 shows the GPC analysis results of aromatic oxycarbonyl compound (C1), and Figure 16 shows the IR analysis results of aromatic oxycarbonyl compound (C1).

[0340] <Comparative Example 2: Synthesis of Aromatic Oxycarbonyl Compounds (C2)>

[0341] In the theoretical structure shown in formula (2c) above, n=2 and the equivalent amount of the active ester group is 221 g / eq., in Example 2, 105 g of solid was obtained in the same manner as in Example 2, except that 64.85 g (0.2 mol, Sanko Co., Ltd.) of HCA-HQ (10-(2,5-dihydroxyphenyl)-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide) was used instead of 62.06 g (0.2 mol, Tokyo Chemical Industry Co., Ltd.) and 28.83 g (0.2 mol) of 1-naphthol was used instead of 34.04 g (0.2 mol, Tokyo Chemical Industry Co., Ltd.).

[0342] From the GPC and IR analysis results, it was confirmed that the obtained solid material has the target molecular structure, i.e., the structure of a phosphorus-containing aromatic oxycarbonyl compound relating to the theoretical structure shown in formula (2c) above. The obtained aromatic oxycarbonyl compound is referred to as "aromatic oxycarbonyl compound (C2)". Figure 17 shows the GPC analysis results of aromatic oxycarbonyl compound (C2), and Figure 18 shows the IR analysis results of aromatic oxycarbonyl compound (C2).

[0343] [Evaluation of Solvent Solubility and Resin Solubility] <Solvent Solubility Evaluation> Synthesized aromatic oxycarbonyl compounds (1) to (7), (C1) and (C2) were stirred and mixed with toluene, MEK (methyl ethyl ketone), or cyclohexanone, respectively, at room temperature, and solubility was visually confirmed. The results are shown in Table 1. ○: Soluble at 40% by mass or more of solids △: Soluble at 10% by mass or more and less than 40% by mass of solids ×: Insoluble or soluble at less than 10% by mass of solids

[0344] <Resin Solubility Evaluation> Synthesized aromatic oxycarbonyl compounds (1) to (7), (C1) and (C2) were melt-mixed at 150°C with either bisphenol A type liquid epoxy resin (DIC Corporation "850-S", epoxy equivalent 183 g / eq.) or biphenyl aralkyl type epoxy resin (Nippon Kayaku Co., Ltd. "NC-3000", epoxy equivalent 275 g / eq.). The solubility of the aromatic oxycarbonyl compounds at 150°C and after cooling to room temperature (presence or absence of precipitation) was visually confirmed. The results are shown in Table 1.

[0345] <<Evaluation Criteria for Solubility When Melted and Mixed at 150°C>> ○: Soluble at 40% by mass or more of aromatic oxycarbonyl compounds △: Soluble at 10% by mass or more but less than 40% by mass of aromatic oxycarbonyl compounds ×: Insoluble or soluble at less than 10% by mass of aromatic oxycarbonyl compounds

[0346] <<Evaluation Criteria for Solubility (Precipitation) When Cooled to Room Temperature>> ○: Soluble at 40% by mass or more of the aromatic oxycarbonyl compound (no precipitation) △: Soluble at 10% by mass or more and less than 40% by mass of the aromatic oxycarbonyl compound (no precipitation) ×: Insoluble (precipitation occurs), or soluble at less than 10% by mass of the aromatic oxycarbonyl compound (no precipitation)

[0347] <Examples 8-14 and Comparative Examples 3 and 4> (1) Preparation of Resin Compositions The aromatic oxycarbonyl compounds (1) to (7), (C1) and (C2) synthesized in the compositions shown in Table 2, bisphenol A type liquid epoxy resin (DIC Corporation "850-S", epoxy equivalent 183 g / eq.), and biphenyl aralkyl type epoxy resin (Nippon Kayaku Co., Ltd. "NC-3000", epoxy equivalent 275 g / eq.) were melt-mixed at 150°C. Then, 4-dimethylaminopyridine (Koei Chemical Industry Co., Ltd. "DMAP") was mixed in to prepare the resin composition.

[0348] (2) Manufacturing of the cured product The prepared resin composition was filled into a mold (100 mm x 100 mm x 0.5 mm) coated with a release agent, and heated and cured at 150°C for 10 minutes to obtain a cured product. The cured product was removed from the mold, and the cured product was further heated and cured at 200°C for 3 hours to produce a sheet-like cured product. In Comparative Example 3, the resin composition did not melt and precipitated due to the aromatic oxycarbonyl compound (C1), so it was not possible to produce a cured product.

[0349] (3) Evaluation of the cured products The sheet-like cured products produced in Examples 8 to 14 were evaluated according to the following procedure. The results are shown in Table 2.

[0350] [Dielectric Properties] The sheet-like cured material was cut into test pieces of a predetermined size, and the dielectric constant and dielectric loss tangent of the cured resin composition were measured using the cavity resonance perturbation method with an analytical instrument (Agilent Technologies HP8362B) at a measurement frequency of 5.8 GHz and a measurement temperature of 23°C. Measurements were performed on five test pieces for each cured material (n=5), and the average value was calculated.

[0351] [Heat Resistance] The sheet-like cured material was cut into test pieces of a predetermined size, and the glass transition temperature (Tg) was measured using a dynamic viscoelasticity measuring device (EXSTAR6000, manufactured by SII Nanotechnology Co., Ltd.) under measurement conditions of a load of 200 mN and a heating rate of 2°C / min.

[0352] As shown in Table 1, the aromatic oxycarbonyl compounds of the present invention exhibited excellent solubility in organic solvents and other resins. Furthermore, as shown in Table 2, when the aromatic oxycarbonyl compounds of the present invention were used as a component of a resin composition, the compounds exhibited excellent solubility, allowing for the production of cured products, which showed excellent heat resistance and dielectric properties. In addition, when the aromatic oxycarbonyl compounds of the present invention containing phosphorus were used as a component of a resin composition, the cured products exhibited excellent flame retardancy.

Claims

1. An aromatic oxycarbonyl compound represented by the following formula (1). (In the formula, X Ａ Each independently represents a monovalent organic group containing at least one aromatic ring (a), X Ｂ Each independently represents a divalent organic group containing at least one aromatic ring (b), X Ｃ Each independently represents a divalent organic group containing at least one aromatic ring (c), and n represents an integer of 1 or more. However, at least one X Ａ However, it is a monovalent organic group represented by the following formula (A-1), and at least one X Ｃ However, it is a divalent organic group represented by the following formula (C-1). (In the formula, Ar represents an aromatic group, and R Ａ１ Each of these independently represents a monovalent organic group containing at least one aromatic ring, na1 represents an integer from 1 to 7, and * represents a bond. (In the formula, Ar Ｃ１ (where * represents an aromatic group, and * represents a bond.) 2. In equation (1), the two X Ａ The aromatic oxycarbonyl compound according to claim 1, wherein the group is a monovalent organic group represented by the above formula (A-1).

3. The aromatic oxycarbonyl compound according to claim 1, wherein Ar in formula (A-1) is an aromatic hydrocarbon group.

4. The aromatic oxycarbonyl compound according to claim 1, wherein in formula (A-1), Ar is an aromatic group having 6 to 14 carbon atoms.

5. In formula (A-1), R Ａ１ are each independently a monovalent organic group represented by the following formula (A-2), the aromatic oxycarbonyl compound according to claim 1. (In formula (A-2), L Ａ１ represents a single bond or an alkylene group, and ring Ar Ａ１ represents an optionally substituted aromatic ring, and * represents a binding site.) 6. In formula (A-2), L Ａ１ The aromatic oxycarbonyl compound according to claim 5, wherein the bond is a single bond.

7. In formula (A-2), ring Ar Ａ１ The aromatic oxycarbonyl compound according to claim 5, wherein the aromatic carbon ring may have substituents.

8. In formula (A-2), ring Ar Ａ１ The aromatic oxycarbonyl compound according to claim 5, wherein the aromatic ring has 6 to 14 carbon atoms and may have substituents.

9. The aromatic oxycarbonyl compound according to claim 1, wherein the aromatic ring (b) is an aromatic carbocyclic ring having 6 to 14 carbon atoms, which may have one or more substituents selected from halogen atoms, alkyl groups, aryl groups, and arylalkyl groups.

10. In formula (C-1), Ar Ｃ１ The aromatic oxycarbonyl compound according to claim 1, wherein the aromatic hydrocarbon group is an aromatic hydrocarbon group.

11. In formula (C-1), Ar Ｃ１ The aromatic oxycarbonyl compound according to claim 1, wherein the aromatic group has 6 to 14 carbon atoms.

12. The aromatic oxycarbonyl compound according to claim 1, wherein n is an integer between 1 and 6.

13. An aromatic oxycarbonyl compound which is a condensate of a compound represented by the following formula (X-1), a compound represented by the following formula (X-2), and a divalent aromatic carboxylic acid halide compound or a divalent aromatic carboxylic acid compound. (In the formula, Ar represents an aromatic group, and R Ａ１ Each independently represents a monovalent organic group containing at least one aromatic ring, na1 represents an integer from 1 to 7, and Ar Ｃ１ (This represents an aromatic group.) 14. A method for producing an aromatic oxycarbonyl compound, comprising the step of reacting a compound represented by the following formula (X-1), a compound represented by the following formula (X-2), and a divalent aromatic carboxylic acid halide compound or a divalent aromatic carboxylic acid compound. (In the formula, Ar represents an aromatic group, and R Ａ１ Each independently represents a monovalent organic group containing at least one aromatic ring, na1 represents an integer from 1 to 7, and Ar Ｃ１ (This represents an aromatic group.) 15. An epoxy resin curing agent comprising an aromatic oxycarbonyl compound according to any one of claims 1 to 13.

16. A resin composition comprising (A) an aromatic oxycarbonyl compound according to any one of claims 1 to 13, and (B) an epoxy resin.

17. The resin composition according to claim 16, further comprising (C) a curing accelerator.

18. The resin composition according to claim 16, further comprising an epoxy resin curing agent other than component (A) (hereinafter referred to as "component (D)").

19. The resin composition according to claim 16, further comprising (E) a thermoplastic resin.

20. The resin composition according to claim 16, further comprising (F) an inorganic filler.

21. The resin composition according to claim 16, further comprising (I) an organic solvent.

22. The resin composition according to claim 16, for use as an insulating layer for a circuit board.

23. The resin composition according to claim 16, for use in semiconductor encapsulation.

24. A resin sheet comprising a support and a layer of the resin composition according to claim 16 provided on the support.

25. The resin sheet according to claim 24, wherein the support is a thermoplastic resin film or a metal foil.

26. A prepreg comprising a sheet-like fibrous substrate impregnated with the resin composition described in claim 16.

27. A cured product of the resin composition according to claim 16.

28. A circuit board comprising an insulating layer having a cured product of the resin composition described in claim 16.

29. A semiconductor chip package comprising a sealing layer having a cured product of the resin composition described in claim 16.

30. The semiconductor chip package according to claim 29, which is a fan-out type package.

31. A semiconductor device comprising the circuit board described in claim 28.

32. A semiconductor device comprising the semiconductor chip package described in claim 29.

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