Aromatic oxycarbonyl compound, resin composition, resin sheet, prepreg, cured product, circuit substrate, semiconductor chip package, and semiconductor device

Abstract

Provided is an aromatic oxycarbonyl compound that when combined with an epoxy resin produces a cured product exhibiting excellent dielectric properties. The aromatic oxycarbonyl compound is represented by general formula (1-1) or general formula (1-2). (In the formula, each of XA1 and XA2 independently represents a monovalent organic group containing at least one aromatic ring (a), each XB independently represents a divalent organic group containing at least one aromatic ring (b), each XC independently represents a divalent organic group containing at least one aromatic ring (c), at least one XC represents a divalent group represented by formula (C-1), and n represents an integer of 1 or more.) (In the formula, RC1 represents a divalent organic group, each RC2 independently represents an alkyl group or a halogen atom, nc1 and nc2 each independently represent an integer of 0-6, and * represents a bond.)

Description

Aromatic oxycarbonyl compound, resin composition, resin sheet, prepreg, cured product, circuit board, semiconductor chip package, and semiconductor device

[0001] The present invention relates to an aromatic oxycarbonyl compound, and further to 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.

[0002] Resin compositions containing a thermosetting resin such as an epoxy resin and a curing agent thereof produce cured products that have excellent insulating properties, heat resistance, adhesion, etc., and have therefore been widely used as materials for electronic components such as circuit boards and semiconductor chip packages.

[0003] On the other hand, in high-speed communications such as the fifth-generation mobile communications system (5G), transmission loss becomes an issue when operating in a high-frequency environment. This requires insulating materials with excellent dielectric properties (low dielectric constant, low dielectric dissipation factor). Furthermore, the amount of heat generated by electronic components tends to increase when operating in a high-frequency environment, so insulating materials used in high-speed communications applications must also have improved heat resistance.

[0004] As an insulating resin material having excellent dielectric properties, for example, Patent Document 1 discloses an active ester resin, which is a reaction product of a divalent aromatic hydroxy compound and an aromatic diacid chloride, as a curing agent for epoxy resin.

[0005] JP 2009-235165 A

[0006] The active ester resin described in Patent Document 1 has significantly better dielectric properties than conventional phenolic curing agents, but does not achieve a satisfactory level of transmission loss required for 5G applications. Furthermore, the cured product obtained using the active ester resin may not have sufficient heat resistance.

[0007] An object of the present invention is to provide a novel aromatic oxycarbonyl compound which, when combined with an epoxy resin, gives a cured product exhibiting excellent dielectric properties and good heat resistance.

[0008] As a result of extensive investigations, the present inventors have found that the above problems can be solved by using an aromatic oxycarbonyl compound having the following structure, and have thus completed the present invention.

[0009] That is, the present invention includes the following: <1> An aromatic oxycarbonyl compound represented by the following general formula (1-1) or general formula (1-2). (In the formula, X Ａ１ and X Ａ２ each independently represents a monovalent organic group containing at least one aromatic ring (a); Ｂ each independently represents a divalent organic group containing at least one aromatic ring (b); Ｃ each independently represents a divalent organic group containing at least one aromatic ring (c), Ｃ represents a divalent group represented by the following formula (C-1), and n represents an integer of 1 or more. (In the formula, R Ｃ１ represents a divalent organic group, R Ｃ２ each independently represent a halogen atom or an alkyl group, nc1 and nc2 each independently represent an integer of 0 to 6, and * represents a bond. <2> The aromatic oxycarbonyl compound according to <1>, wherein the divalent group represented by formula (C-1) is a divalent group represented by the following formula (C-2): (In the formula, R Ｃ２ , nc1 and nc2 are the same as above, and R Ｃ３ represents a hydrogen atom or a monovalent organic group, and * represents a bond. Ｃ３ <4> The aromatic oxycarbonyl compound according to <2>, wherein R represents a hydrogen atom or a monovalent aromatic group which may have a substituent. Ｃ３represents a hydrogen atom. <5> The aromatic oxycarbonyl compound according to any one of <2> to <4>, wherein nc1 and nc2 are 0. <6> The aromatic oxycarbonyl compound according to any one of <1> to <5>, wherein the aromatic ring (a) 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. <7> The aromatic oxycarbonyl compound according to any one of <1> to <6>, 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. <8> The aromatic oxycarbonyl compound according to any one of <1> to <7>, wherein the aromatic ring (c) 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. <9> The aromatic oxycarbonyl compound according to any one of <1> to <8>, wherein n represents an integer of 1 or more and 6 or less. <10> The aromatic oxycarbonyl compound according to any one of <1> to <9>, represented by formula (1-1). <11> The aromatic oxycarbonyl compound according to any one of <1> to <9>, wherein X per molecule of the aromatic oxycarbonyl compound is Ａ１ or X Ａ２ The number of nA, X Ｂ The number of nB, X Ｃ Let nC be the number of X Ａ１ , X Ａ２ , X Ｂ and X Ｃ <12> The aromatic oxycarbonyl compound according to any one of <1> to <11>, which is a condensation reaction product of: (x1) a divalent aromatic hydroxy compound containing at least a compound represented by the following general formula (x1), (x2) a divalent aromatic carboxylic acid compound or a divalent aromatic carboxylic acid halide compound, and (x3) a monovalent aromatic hydroxy compound, or a monovalent aromatic carboxylic acid compound or a monovalent carboxylic acid halide compound: (In the formula, R Ｃ１ , R Ｃ２ , nc1 and nc2 are the same as above.) <13> A method for producing an aromatic oxycarbonyl compound, comprising: (1) a step of obtaining a divalent aromatic hydroxy compound represented by the following general formula (x1) (hereinafter referred to as "divalent aromatic hydroxy compound (x1)") by a condensation reaction between (x1a) a naphthol which may have a substituent and (x1b) an aldehyde compound; and (2) a step of condensing the obtained divalent aromatic hydroxy compound (x1), (x2) a divalent aromatic carboxylic acid compound or a divalent aromatic carboxylic acid halide compound, and (x3) a monovalent aromatic hydroxy compound, or a monovalent aromatic carboxylic acid compound or a monovalent carboxylic acid halide compound. (In the formula, R Ｃ１ represents a divalent organic group, R Ｃ２each independently represent a substituent, and nc1 and nc2 each independently represent an integer of 0 to 6.) <14> A method for producing an aromatic oxycarbonyl compound according to <13>, comprising subjecting the obtained product containing the divalent aromatic hydroxy compound (x1) to a condensation reaction between (x2) a divalent aromatic carboxylic acid compound or a divalent aromatic carboxylic acid halide compound and (x3) a monovalent aromatic hydroxy compound, or a monovalent aromatic carboxylic acid compound or a monovalent carboxylic acid halide compound, without purification or drying. <15> An epoxy resin curing agent comprising the aromatic oxycarbonyl compound according to any one of <1> to <12>. <16> A resin composition comprising the aromatic oxycarbonyl compound according to any one of <1> to <12> and an epoxy resin. <17> The resin composition according to <16>, further comprising an inorganic filler. <18> The resin composition according to <16> or <17>, further comprising an organic solvent. <19> The resin composition according to any one of <16> to <18>, which is used for an insulating layer of a circuit board. <20> The resin composition according to any one of <16> to <18>, which is used for encapsulating a semiconductor. <21> A resin sheet comprising a support and a layer of the resin composition according to any one of <16> to <20> provided on the support. <22> The resin sheet according to <21>, in which the support is a thermoplastic resin film or a metal foil. <23> A prepreg obtained by impregnating a sheet-like fiber base material with the resin composition according to any one of <16> to <20>. <24> A cured product of the resin composition according to any one of <16> to <20>. <25> A circuit board comprising an insulating layer comprising a cured product of the resin composition according to any one of <16> to <19>. <26> A semiconductor chip package comprising an encapsulating layer comprising a cured product of the resin composition according to any one of <16> to <18> and <20>. <27> The semiconductor chip package according to <26>, which is a fan-out package. <28> A semiconductor device comprising the circuit board according to <25>. <29> A semiconductor device comprising the semiconductor chip package according to <26> or <27>.

[0010] According to the present invention, there can be provided a novel aromatic oxycarbonyl compound which, when combined with an epoxy resin, gives a cured product exhibiting excellent dielectric properties and good heat resistance.

[0011] <Explanation of Terms> In this specification, the term "optionally substituted" used in reference to a compound or group means both a case where the hydrogen atoms of the compound or group are not substituted with substituents, and a case where some or all of the hydrogen atoms of the compound or group are substituted with substituents.

[0012] In this specification, unless otherwise specified, the term "substituent" refers to a halogen atom, an alkyl group, an alkenyl group, an alkynyl group, an alkapolyenyl group, a cycloalkyl group, a cycloalkenyl group, an alkoxy group, a cycloalkyloxy group, an aryl group, an aryloxy group, an arylalkyl group, an arylalkoxy group, a monovalent heterocyclic group, an alkylidene group, an amino group, a silyl group, an acyl group, an acyloxy group, a (meth)acryloyl group, a carboxy group, a sulfo group, a cyano group, a nitro group, a hydroxy group, a mercapto group, or an oxo group. Groups containing only carbon and hydrogen, such as alkyl groups, alkenyl groups, alkynyl groups, alkapolyenyl groups, cycloalkyl groups, cycloalkenyl groups, aryl groups, arylalkyl groups, and alkylidene groups, are also collectively referred to as "hydrocarbon groups." Groups having an unsaturated bond, such as alkenyl groups, alkynyl groups, alkapolyenyl groups, cycloalkenyl groups, and (meth)acryloyl groups, are also collectively referred to as "unsaturated bond-containing groups." Here, the term "(meth)acryloyl group" means both an acryloyl group and a methacryloyl group.

[0013] Examples of the halogen atom used as a substituent include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0014] The alkyl group used as a substituent may be either 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, still more preferably 1 to 6, and particularly preferably 1 to 3. Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, and a decyl group.

[0015] The alkenyl group used as a substituent may be either 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, still more preferably 2 to 6, and particularly preferably 2 or 3. Examples of the alkenyl group include a vinyl group, an allyl group, a 1-propenyl group, a butenyl group, a sec-butenyl group, an isobutenyl group, a tert-butenyl group, a pentenyl group, a hexenyl group, a heptenyl group, an octenyl group, a nonenyl group, and a decenyl group.

[0016] The alkynyl group used as a substituent may be either 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, still more preferably 2 to 6, and particularly preferably 2 or 3. Examples of the alkynyl group include an ethynyl group, a propynyl group, a butynyl group, a sec-butynyl group, an isobutynyl group, a tert-butynyl group, a pentynyl group, a hexynyl group, a heptynyl group, an octynyl group, a nonynyl group, and a decynyl group.

[0017] The alkapolyenyl group used as a substituent may be either 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 still more preferably 2. The number of carbon atoms in the alkapolyenyl group is preferably 3 to 20, more preferably 3 to 14, even more preferably 3 to 12, and still more preferably 3 to 6.

[0018] 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 a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.

[0019] 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 a cyclopropenyl group, a cyclobutenyl group, a cyclopentenyl group, and a cyclohexenyl group.

[0020] The alkoxy group used as a substituent may be either 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 a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butoxy group, a sec-butoxy group, an isobutoxy group, a tert-butoxy group, a pentyloxy group, a hexyloxy group, a heptyloxy group, an octyloxy group, a nonyloxy group, and a decyloxy group.

[0021] 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 a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group, and a cyclohexyloxy group.

[0022] The aryl group used as a substituent is a group in which one hydrogen atom on the aromatic ring has been removed from 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 a phenyl group, a naphthyl group, and an anthracenyl group.

[0023] 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 the aryloxy group used as a substituent include a phenoxy group, a 1-naphthyloxy group, and a 2-naphthyloxy group.

[0024] 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 group, naphthyl-C １ ~C １２ Alkyl groups, and anthracenyl-C １ ~C １２ Examples of suitable alkyl groups include:

[0025] 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 groups, and naphthyl-C １ ~C １２ Examples include alkoxy groups.

[0026] A monovalent heterocyclic group used as a substituent refers to a group in which one hydrogen atom has been removed 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 a thienyl group, a pyrrolyl group, a furanyl group, a furyl group, a pyridyl group, a pyridazinyl group, a pyrimidyl group, a pyrazinyl group, a triazinyl group, a pyrrolidyl group, a piperidyl group, a quinolyl group, and an isoquinolyl group.

[0027] The alkylidene group used as a substituent refers to a group in which two hydrogen atoms have been removed 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, still more preferably 1 to 6, and particularly preferably 1 to 3. Examples of the alkylidene group include a methylidene group, an ethylidene group, a propylidene group, an isopropylidene group, a butylidene group, a sec-butylidene group, an isobutylidene group, a tert-butylidene group, a pentylidene group, a hexylidene group, a heptylidene group, an octylidene group, a nonylidene group, and a decylidene group.

[0028] The acyl group used as a substituent refers to 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 either linear or branched. Examples of the aryl group represented by R include a phenyl group, a naphthyl group, and an 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 an acetyl group, a propionyl group, a butyryl group, an isobutyryl group, a pivaloyl group, and a benzoyl group.

[0029] The acyloxy group used as a substituent refers to 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 either linear or branched. Examples of the aryl group represented by R include a phenyl group, a naphthyl group, and an 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 an acetoxy group, a propionyloxy group, a butyryloxy group, an isobutyryloxy group, a pivaloyloxy group, and a benzoyloxy group.

[0030] The above-mentioned substituents may further have a substituent (hereinafter, sometimes referred to as a "secondary substituent"). Unless otherwise specified, the secondary substituent may be the same as the above-mentioned substituent.

[0031] As used herein, the term "organic group" refers to a group containing at least carbon atoms as skeletal atoms, and may be linear, branched, or cyclic. Unless otherwise specified, the number of skeletal atoms in an organic group is preferably 1 to 3,000, more preferably 1 to 1,000, even more preferably 1 to 100, still more preferably 1 to 50, and particularly preferably 1 to 30 or 1 to 20. Examples of organic groups include groups containing one or more skeletal atoms (including at least a carbon atom) selected from carbon atoms, oxygen atoms, nitrogen atoms, and sulfur atoms.

[0032] As used herein, the term "hydrocarbon group" refers to a group obtained by removing one or more hydrogen atoms from a hydrocarbon compound. 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 described below that contain only carbon atoms and hydrogen atoms. As used herein, an aliphatic group containing only carbon atoms and hydrogen atoms is also referred to as an "aliphatic hydrocarbon group," and an aromatic group containing only carbon atoms and hydrogen atoms is also referred to as an "aromatic hydrocarbon group."

[0033] As used herein, the term "aliphatic group" refers to a group obtained by removing one or more hydrogen atoms bonded to an aliphatic carbon of an aliphatic compound. Specifically, a monovalent aliphatic group refers to a group obtained by removing one hydrogen atom bonded to an aliphatic carbon of an aliphatic compound, and a divalent aliphatic group refers to a group obtained by removing two hydrogen atoms bonded to an aliphatic carbon of an aliphatic compound. 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 alkapolyenylene groups (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). 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, and is 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 a substituent is not included in this number of carbon atoms.

[0034] As used herein, the term "aromatic group" refers to a group in which one or more hydrogen atoms have been removed from the aromatic ring of an aromatic compound. Specifically, a monovalent aromatic group refers to a group in which one hydrogen atom has been removed from the aromatic ring of an aromatic compound, and a divalent aromatic group refers to a group in which two hydrogen atoms have been removed from the aromatic ring of an aromatic compound. Examples of monovalent aromatic groups include aryl groups which may have a substituent and heteroaryl groups which may have a substituent. Examples of divalent aromatic groups include arylene groups which may have a substituent and heteroarylene groups which may have a substituent. In this specification, unless otherwise specified, the number of carbon atoms in the aromatic group is preferably 3 or more, more preferably 4 or more or 5 or more, and even more preferably 6 or more, and the upper limit is 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 the substituent.

[0035] As used herein, the term "aromatic ring" refers to a ring conforming to Hückel's rule, in which the number of electrons contained in the π-electron system on the ring is 4p+2 (p is a natural number), and includes monocyclic aromatic rings and fused polycyclic aromatic rings in which two or more monocyclic aromatic rings are fused together. The aromatic ring may be an aromatic carbocyclic ring having only carbon atoms as ring-constituting atoms, or an aromatic heterocyclic ring having heteroatoms such as oxygen atoms, nitrogen atoms, and sulfur atoms in addition to carbon atoms as ring-constituting atoms. As used herein, unless otherwise specified, the number of carbon atoms in the aromatic ring is preferably 3 or more, more preferably 4 or more or 5 or more, and even more preferably 6 or more, and the upper limit is 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. Examples of aromatic rings include monocyclic aromatic rings such as a benzene ring, a furan ring, a thiophene ring, a pyrrole ring, a pyrazole ring, an oxazole ring, an isoxazole ring, a thiazole ring, an imidazole ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, and a pyrazine ring; and condensed polycyclic aromatic rings in which two or more monocyclic aromatic rings are condensed, such as a naphthalene ring, an anthracene ring, a phenanthrene ring, a benzofuran ring, an isobenzofuran ring, an indole ring, an isoindole ring, a benzothiophene ring, a benzimidazole ring, an indazole ring, a benzoxazole ring, a benzisoxazole ring, a benzothiazole ring, a quinoline ring, an isoquinoline ring, a quinoxaline ring, an acridine ring, a quinazoline ring, a cinnoline ring, and a phthalazine ring. In this specification, the carbon atoms constituting the aromatic ring are referred to as "aromatic carbons".

[0036] The present invention will be described in detail below with reference to preferred embodiments thereof. However, the present invention is not limited to the following embodiments and examples, and can be implemented with any modifications within the scope of the claims of the present invention and their equivalents.

[0037] [Aromatic Oxycarbonyl Compound] The aromatic oxycarbonyl compound of the present invention is characterized by being represented by the following general formula (1-1) or (1-2).

[0038] (In the formula, X Ａ１ and X Ａ２each independently represents a monovalent organic group containing at least one aromatic ring (a); Ｂ each independently represents a divalent organic group containing at least one aromatic ring (b); Ｃ each independently represents a divalent organic group containing at least one aromatic ring (c), Ｃ represents a divalent group represented by the following formula (C-1), and n represents an integer of 1 or more.

[0039] (In the formula, R Ｃ１ represents a divalent organic group, R Ｃ２ each independently represents a substituent, nc1 and nc2 each independently represent an integer of 0 to 6, and * represents a bond.

[0040] The aromatic oxycarbonyl compound of the present invention is a compound having at least X containing a divalent group represented by the above formula (C-1) (hereinafter also referred to as a "bisnaphthol skeleton"). Ｃ And, X Ｂ By containing a structural unit which is an oligomer unit of the above, when combined with an epoxy resin, a cured product exhibiting excellent dielectric properties and good heat resistance can be obtained. The present inventors have also confirmed that when combined with an epoxy resin, the aromatic oxycarbonyl compound of the present invention can produce a cured product which is excellent in smear removal during via hole formation and which can suppress the halo phenomenon. Here, the halo phenomenon refers to a phenomenon in which the insulating layer resin around a via hole deteriorates during via hole formation. Degraded areas where such halo phenomenon occurs are easily eroded by chemical solutions such as roughening solutions, causing interlayer delamination between the insulating layer and the inner layer substrate, ultimately resulting in a deterioration in electrical conductivity reliability.

[0041] The method for producing the aromatic oxycarbonyl compound of the present invention will be described later. Ｃ —OH) and a divalent aromatic carboxylic acid compound or a divalent aromatic carboxylic acid halide compound (Y—C(═O)—X Ｂ-C(=O)-Y; wherein Y represents a hydroxy group or a halogen atom), Ａ１ When a monovalent aromatic carboxylic acid compound or a monovalent aromatic carboxylic acid halide compound (X Ａ２ -C(=O)-Y; wherein Y has the same meaning as above), an aromatic oxycarbonyl compound represented by formula (1-2) is obtained.

[0042] -monovalent organic group X Ａ１ and X Ａ２ In formula (1-1), X Ａ１ Each of X independently represents a monovalent organic group containing at least one aromatic ring (a). Ａ２ each independently represents a monovalent organic group containing at least one aromatic ring (a).

[0043] X Ａ１ and X Ａ２ As described above, the aromatic ring (a) contained in the monovalent organic group represented by the formula (I) may be either a monocyclic aromatic ring or a fused polycyclic aromatic ring in which two or more monocyclic aromatic rings are fused. In addition, the aromatic ring may be either an aromatic carbon ring or an aromatic heterocycle.

[0044] From the viewpoint of providing a cured product exhibiting even better dielectric properties and heat resistance in combination with an epoxy resin, the aromatic ring (a) is preferably an aromatic carbocyclic ring. The aromatic carbocyclic ring may be either a monocyclic aromatic carbocyclic ring or a condensed polycyclic aromatic carbocyclic ring, and the number of carbon atoms therein is preferably 6 to 14, more preferably 6 to 10. Therefore, in a preferred embodiment, X Ａ１ and X Ａ２ The aromatic ring (a) contained in the monovalent organic group represented by the formula (I) is an aromatic carbon ring having 6 to 14 carbon atoms.

[0045] In order to obtain a cured product that exhibits even better dielectric properties and heat resistance in combination with an epoxy resin, X Ａ１ and X Ａ２The number of aromatic rings (a) contained in the monovalent organic group represented by X Ａ１ or X Ａ２ The number per ring is preferably 1 to 3, more preferably 1 or 2. The number of aromatic rings (a) does not include the number of aromatic rings as substituents.

[0046] The aromatic ring (a) may have a substituent, as described above, and among these, from the viewpoint of providing a cured product that exhibits both better dielectric properties and heat resistance in combination with an epoxy resin, it is preferably one or more selected from a halogen atom, a hydrocarbon group, and an alkoxy group, more preferably one or more selected from a halogen atom, an alkyl group, an aryl group, and an arylalkyl group, and even more preferably 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.

[0047] Thus, in one preferred embodiment, X Ａ１ and X Ａ２ The aromatic ring (a) contained in the monovalent organic group represented by the formula (I) is an aromatic carbon 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.

[0048] X Ａ１ and X Ａ２ The monovalent organic group represented by the formula (I) is not particularly limited as long as it contains at least one aromatic ring (a) as described above, and is a group containing at least a carbon atom as a skeletal atom, as described above. Preferably, the monovalent organic group is a monovalent group consisting of one or more (preferably 1 to 100, 1 to 50, or 1 to 30) skeletal atoms selected from carbon atoms, oxygen atoms, nitrogen atoms, and sulfur atoms. Among these, from the viewpoint of providing a cured product that exhibits both even better dielectric properties and heat resistance in combination with an epoxy resin, X Ａ１ and X Ａ２ It is particularly preferable that the monovalent organic group represented by the formula (I) contains only carbon atoms or only carbon atoms and oxygen atoms as skeletal atoms. The suitable range of the number of skeletal atoms is as described above, and among these, 6 to 30 or 10 to 30 is preferable.

[0049] In order to obtain a cured product that exhibits both good dielectric properties and good heat resistance in combination with an epoxy resin, X Ａ１ The oxygen atom bonded to X Ａ１ From the same viewpoint, it is preferable that X in the general formula (1-2) is bonded to the aromatic carbon atom of X, that is, the carbon atom constituting the aromatic ring (a). Ａ２ The oxygen atom bonded to X Ａ２ It is preferred that the aromatic carbon atom of the formula (a) is bonded to the aromatic carbon atom of the formula (a), i.e., the carbon atom constituting the aromatic ring (a).

[0050] In one preferred embodiment, X Ａ１ and X Ａ２ are each independently represented by the following formula (A-1) or (A-2).

[0051] (In the formula, R Ａ１ and R Ａ２ each independently represents a substituent, na1 represents an integer of 0 to 5, each na2 independently represents an integer of 0 to 7, and * represents a bond.

[0052] In formula (A-1), one benzene ring is clearly shown. This benzene ring is X Ａ１ and X Ａ２ corresponds to the aforementioned "aromatic ring (a)". Ａ１ and X Ａ２ is represented by formula (A-1), it is a monovalent organic group containing one benzene ring. Ａ１ Suitable examples of the substituent represented by X Ａ１ and X Ａ２ Among these, one or more selected from a halogen atom, an alkyl group, an aryl group, and an arylalkyl group are more preferred, 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 are even more preferred. na1 represents an integer of 0 to 5, and may, for example, represent an integer of 0 to 3, or 0 or 1.

[0053] In formula (A-2), one naphthalene ring is clearly shown. This naphthalene ring is X Ａ１ and X Ａ２ corresponds to the aforementioned "aromatic ring (a)". Ａ１ and X Ａ２ is represented by formula (A-2), it is a monovalent organic group containing one naphthalene ring. Ａ２ Suitable examples of the substituent represented by X Ａ１ and X Ａ２ Among these, one or more selected from a halogen atom, an alkyl group, an aryl group, and an arylalkyl group are more preferred, 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 are even more preferred. na2 represents an integer of 0 to 7, and may represent, for example, an integer of 0 to 4, an integer of 0 to 3, or 0 or 1.

[0054] In formula (1-1), two X Ａ１ may be the same or different. Ａ２ may be the same or different.

[0055] -divalent organic group X Ｂ Regardless of whether it is formula (1-1) or formula (1-2), X Ｂ each independently represents a divalent organic group containing at least one aromatic ring (b).

[0056] X Ｂ As described above, the aromatic ring (b) contained in the divalent organic group represented by the formula (I) may be either a monocyclic aromatic ring or a fused polycyclic aromatic ring. In addition, the aromatic ring may be either an aromatic carbon ring or an aromatic heterocycle.

[0057] From the viewpoint of providing a cured product that exhibits even better dielectric properties and heat resistance in combination 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 condensed polycyclic aromatic carbocyclic ring, and the number of carbon atoms therein 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 the formula (I) is an aromatic carbon ring having 6 to 14 carbon atoms.

[0058] In order to obtain a cured product that exhibits even better dielectric properties and heat resistance in combination with an epoxy resin, X Ｂ The number of aromatic rings (b) contained in the divalent organic group represented by X Ｂ The number per ring is preferably 1 to 3, more preferably 1 or 2. The number of aromatic rings (b) does not include the number of aromatic rings as substituents.

[0059] The aromatic ring (b) may have a substituent, as described above, and among these, from the viewpoint of providing a cured product that exhibits both better dielectric properties and heat resistance in combination with an epoxy resin, it is preferably one or more selected from a halogen atom, a hydrocarbon group, and an alkoxy group, more preferably one or more selected from a halogen atom, an alkyl group, an aryl group, and an arylalkyl group, and even more preferably 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.

[0060] Thus, in one preferred embodiment, X Ｂ The aromatic ring (b) contained in the monovalent organic group represented by the formula (I) is an aromatic carbon 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.

[0061] X ＢThe divalent organic group represented by the formula (I) is not particularly limited as long as it contains at least one aromatic ring (b), and as described above, it is a group containing at least a carbon atom as a skeletal atom, but preferably includes a divalent group consisting of one or more (preferably 1 to 100, 1 to 50, or 1 to 30) skeletal atoms selected from carbon atoms, oxygen atoms, nitrogen atoms, and sulfur atoms. Among these, from the viewpoint of providing a cured product that exhibits both even better dielectric properties and heat resistance in combination with an epoxy resin, X Ｂ It is particularly preferable that the divalent organic group represented by the formula (I) contains only carbon atoms or only carbon atoms and oxygen atoms as skeletal atoms. The suitable range of the number of skeletal atoms is as described above, and among these, 6 to 30 or 6 to 20 is preferable.

[0062] In order to obtain a cured product that exhibits both good dielectric properties and good heat resistance in combination with an epoxy resin, X Ｂ The two carbonyl groups bonded to X Ｂ It is preferred that the aromatic carbon atom of the aromatic ring (b) is bonded to the aromatic carbon atom of the aromatic ring (b).

[0063] In one preferred embodiment, X Ｂ are each independently (i) a divalent group obtained by removing two hydrogen atoms from an optionally substituted monocyclic aromatic carbocycle, or (ii) a divalent group obtained by removing two hydrogen atoms from an optionally substituted fused polycyclic aromatic carbocycle. In such an embodiment, the monocyclic aromatic carbocycle or the fused polycyclic aromatic carbocycle is Ｂ corresponds to the above-mentioned "aromatic ring (b)". Ｂ When is the divalent group of (i) above, X Ｂ is a divalent organic group containing one monocyclic aromatic carbocyclic ring. Ｂ When is the divalent group of (ii) above, X Ｂ is a divalent organic group containing one fused polycyclic aromatic carbocycle. Suitable examples of the substituent that the monocyclic aromatic carbocycle or the fused polycyclic aromatic carbocycle may have include X ＢAmong these, one or more selected from a halogen atom, an alkyl group, an aryl group, and an arylalkyl group are more preferred, 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 are even more preferred.

[0064] Among these, in order to obtain a cured product that exhibits even better dielectric properties and heat resistance in combination with an epoxy resin, X Ｂ The divalent organic group represented by the formula (I) is preferably the divalent group (i) above, and more preferably a divalent group obtained by removing two hydrogen atoms from an unsubstituted monocyclic aromatic carbocycle.

[0065] -divalent organic group X Ｃ Regardless of whether it is formula (1-1) or formula (1-2), X Ｃ each independently represents a divalent organic group containing at least one aromatic ring (c).

[0066] X Ｃ As described above, the aromatic ring (c) contained in the divalent organic group represented by the formula (I) may be either a monocyclic aromatic ring or a fused polycyclic aromatic ring. In addition, the aromatic ring may be either an aromatic carbocyclic ring or an aromatic heterocyclic ring.

[0067] From the viewpoint of providing a cured product exhibiting even better dielectric properties and heat resistance in combination with an epoxy resin, the aromatic ring (c) is preferably an aromatic carbocyclic ring. The aromatic carbocyclic ring may be either a monocyclic aromatic carbocyclic ring or a condensed polycyclic aromatic carbocyclic ring, and the number of carbon atoms therein is preferably 6 to 14, more preferably 6 to 10. Therefore, in a preferred embodiment, X Ｃ The aromatic ring (c) contained in the divalent organic group represented by the formula (I) is an aromatic carbon ring having 6 to 14 carbon atoms.

[0068] In order to obtain a cured product that exhibits even better dielectric properties and heat resistance in combination with an epoxy resin, X Ｃ The number of aromatic rings (c) contained in the divalent organic group represented by X ＣThe number per ring is preferably 1 to 7, more preferably 1 to 5 or 1 to 3. The number of aromatic rings (c) does not include the number of aromatic rings as substituents.

[0069] Among these, from the viewpoint of providing a cured product exhibiting even better dielectric properties and heat resistance, X Ｃ represents a divalent organic group containing two or more monocyclic aromatic carbocycles, or a divalent organic group containing at least one fused polycyclic aromatic carbocycle. Here, the number of carbon atoms per monocyclic aromatic carbocycle is as described above, but is preferably 6 (i.e., a benzene ring). The number of carbon atoms per fused polycyclic aromatic carbocycle is as described above, but is preferably 10 to 14 (e.g., a naphthalene ring, an anthracene ring), and more preferably 10.

[0070] X Ｃ Examples of the divalent organic group containing two or more monocyclic aromatic carbocycles include a divalent group obtained by removing two hydroxy groups from a bisphenol compound which may have a substituent, and a divalent group obtained by removing two hydroxy groups from a dihydroxybiphenyl compound which may have a substituent. Preferred embodiments of these will be described later with reference to formula (C-3) below.

[0071] X Ｃ Examples of the divalent organic group containing at least one fused polycyclic aromatic carbocycle, as represented by the formula (C-4), include a divalent group obtained by removing two hydroxy groups from a dihydroxynaphthalene compound which may have a substituent (see formula (C-4) below), and a divalent group obtained by removing two hydroxy groups from a bisnaphthol compound which may have a substituent (see formulas (C-1) and (C-2) below).

[0072] The aromatic ring (c) may have a substituent, as described above, and among these, from the viewpoint of providing a cured product that exhibits both better dielectric properties and heat resistance in combination with an epoxy resin, preferred is one or more selected from a halogen atom, a hydrocarbon group, and an alkoxy group, more preferred is one or more selected from a halogen atom, an alkyl group, an aryl group, and an arylalkyl group, and even more preferred is 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.

[0073] The aromatic oxycarbonyl compound of the present invention comprises at least one X Ｃ represents a divalent group represented by the following formula (C-1): As a result, the aromatic oxycarbonyl compound of the present invention, when combined with an epoxy resin, can provide a cured product that exhibits both good dielectric properties and heat resistance.

[0074] (In the formula, R Ｃ１ represents a divalent organic group, R Ｃ２ each independently represents a substituent, nc1 and nc2 each independently represent an integer of 0 to 6, and * represents a bond.

[0075] In formula (C-1), two naphthalene rings are clearly shown. These two naphthalene rings are X Ｃ That is, X represented by formula (C-1) corresponds to the above-mentioned "aromatic ring (c)". Ｃ is a divalent organic group containing at least two naphthalene rings.

[0076] In formula (C-1), R Ｃ１ represents a divalent organic group. Ｃ１As described above, the divalent organic group represented by R is a group containing at least a carbon atom as a skeletal atom, and preferably includes a divalent group consisting of one or more (preferably 1 to 30, 1 to 20, or 1 to 10) skeletal atoms selected from carbon, oxygen, nitrogen, and sulfur atoms. Among these, from the viewpoint of providing a cured product that exhibits even better dielectric properties and heat resistance in combination with an epoxy resin, R Ｃ１ The divalent organic group represented by R is a divalent hydrocarbon group having 1 to 10 carbon atoms which may have a substituent. Ｃ１ The total number of carbon atoms in the divalent organic group represented by the formula (I) is preferably 1 to 20, more preferably 1 to 15, and even more preferably 1 to 13, 1 to 10, or 1 to 8.

[0077] R Ｃ１ Examples of the divalent hydrocarbon group in include a divalent aliphatic hydrocarbon group and a divalent aromatic hydrocarbon group, such as an alkylene group, a cycloalkylene group, an alkenylene group, a cycloalkenylene group, an alkapolyenylene group (the number of double bonds is preferably 2 to 10, more preferably 2 to 6, even more preferably 2 to 4, and still more preferably 2), an arylene group, and the like. Of these, an alkylene group, a cycloalkylene group, an alkenylene group, a cycloalkenylene group, or an arylene group is preferred, an alkylene group, a cycloalkylene group, or an arylene group is more preferred, and an alkylene group is even more preferred.

[0078] R Ｃ１ The alkylene group in may be either linear or branched, and the number of carbon atoms is more preferably 1 to 6, and even more preferably 1 to 4 or 1 to 3. The number of carbon atoms does not include the number of carbon atoms of the substituent. Examples of the alkylene group include a methylene group, an ethylene group, a propylene group, a butylene group, a pentylene group, and a hexylene group.

[0079] R Ｃ１The number of carbon atoms in the cycloalkylene group in the formula (I) is more preferably 3 to 10, 4 to 10, or 6 to 10. The number of carbon atoms in the substituent is not included in this number of carbon atoms. Examples of the cycloalkylene group include a cyclopropylene group, a cyclobutylene group, a cyclopentylene group, a cyclohexylene group, a decahydronaphthalene group, a norbornanylene group, a dicyclopentanylene group, and an adamantanylene group.

[0080] R Ｃ１ The number of carbon atoms in the arylene group in the formula (I) is more preferably 6 to 10. The number of carbon atoms in the substituent is not included in this number of carbon atoms. Examples of the arylene group include a phenylene group, a naphthylene group, and an indandiyl group.

[0081] R Ｃ１ The substituents that the divalent hydrocarbon group in the formula (I) may have are as described above. Among these, the substituent is preferably one or more selected from alkyl groups and aryl groups, and more preferably one or more selected from alkyl groups having 1 to 6 carbon atoms and aryl groups having 6 to 10 carbon atoms. As described above, these substituents may have a secondary substituent, and the secondary substituent is preferably one or more selected from alkyl groups and aryl groups, and more preferably one or more selected from alkyl groups having 1 to 6 carbon atoms and aryl groups having 6 to 10 carbon atoms.

[0082] In formula (C-1), R Ｃ２ Suitable examples of the substituent represented by X Ｃ In particular, from the viewpoint of providing a cured product that exhibits both even better dielectric properties and heat resistance in combination with an epoxy resin, one or more selected from a halogen atom, a hydrocarbon group, and an alkoxy group are preferred, one or more selected from a halogen atom, an alkyl group, an aryl group, and an arylalkyl group are more preferred, a halogen atom or an alkyl group is even more preferred, and a fluorine atom or an alkyl group having 1 to 6 carbon atoms is even more preferred.

[0083] In formula (C-1), nc1 and nc2 each independently represent an integer of 0 to 6, for example, an integer of 0 to 4, an integer of 0 to 3, or 0 or 1.

[0084] In formula (C-1), the bond * may extend from the 1- or 2-carbon of the naphthalene ring as indicated. However, from the viewpoint of providing a cured product that exhibits even better dielectric properties and heat resistance in combination with an epoxy resin, it is preferable that the bond * extend from the 2-carbon of the naphthalene ring as indicated.

[0085] In formula (C-1), R Ｃ１ may be bonded to the ortho-position or the para-position relative to the bond *, and in particular, the bond * is bonded to the 2-carbon atom of the naphthalene ring, and R Ｃ１ is preferably bonded to the 1-position carbon of the naphthalene ring, which is in the ortho position relative to the bond *, since this allows the effects of the present invention to be more effectively enjoyed.

[0086] In a particularly preferred embodiment from the viewpoint of providing a cured product that exhibits even better dielectric properties and heat resistance in combination with an epoxy resin, the divalent group represented by formula (C-1) is a divalent group represented by the following formula (C-2):

[0087] (In the formula, R Ｃ２ , nc1 and nc2 are the same as above, and R Ｃ３ represents a hydrogen atom or a monovalent organic group, and * represents a bond.

[0088] In formula (C-2), R Ｃ２ , nc1 and nc2 are the same as above, and the preferred types and ranges thereof are also as described above for formula (C-1). In particular, from the viewpoint of particularly favorably enjoying the effects of the present invention, nc1 and nc2 are preferably 0.

[0089] In formula (C-2), R Ｃ３ represents a hydrogen atom or a monovalent organic group. Ｃ３As described above, the monovalent organic group represented by R is a group containing at least a carbon atom as a skeletal atom, and preferably includes a monovalent group consisting of one or more (preferably 1 to 30, 1 to 20, or 1 to 15) skeletal atoms selected from carbon, oxygen, nitrogen, and sulfur atoms. Among these, from the viewpoint of providing a cured product that exhibits even better dielectric properties and heat resistance in combination with an epoxy resin, R Ｃ３ The monovalent organic group represented by R is preferably a monovalent aliphatic group which may have a substituent or a monovalent aromatic group which may have a substituent, more preferably a monovalent aromatic group which may have a substituent, more preferably an aryl group which may have a substituent, and even more preferably an aryl group having 6 to 10 carbon atoms which may have a substituent. Ｃ３ The substituents that the monovalent organic group represented by the formula (I) may have are as described above, but from the viewpoint of being able to enjoy the effects of the present invention more, one or more selected from alkyl groups and aryl groups are preferred, and one or more selected from alkyl groups having 1 to 6 carbon atoms and aryl groups having 6 to 10 carbon atoms are more preferred. Therefore, in a preferred embodiment, R Ｃ３ represents a hydrogen atom or a monovalent aromatic group which may have a substituent, and more preferably represents a hydrogen atom.

[0090] In order to obtain a cured product that exhibits excellent dielectric properties and heat resistance in combination with an epoxy resin, at least one X Ｃ is preferably a divalent group represented by any one of the following formulas (C-2-1) to (C-2-8), and particularly preferably X Ｃ is particularly preferably a divalent group represented by formula (C-2-1) from the viewpoint of achieving the most advantageous effects of the present invention.

[0091]

[0092] As described above, the aromatic oxycarbonyl compound of the present invention has at least one X Ｃ represents a divalent group represented by the above formula (C-1), other divalent organic groups may be substituted by X ＣSuch other divalent organic groups are as described above, but among them, from the viewpoint of being able to further enjoy the effects of the present invention in combination with the divalent group represented by formula (C-1), a divalent group represented by the following formula (C-3) or formula (C-4) is preferred.

[0093] (In the formula, R Ｃ４ represents a single bond or a divalent linking group selected from the group consisting of a divalent hydrocarbon group having 1 to 10 carbon atoms which may have a substituent, an oxygen atom, a sulfonyl group, a carbonyl group, a carbonate group, and combinations thereof; R Ｃ５ and R Ｃ６ each independently represents a substituent; nc3, nc4, and nc5 each independently represent an integer of 0 to 4; and * represents a bond.

[0094] In formula (C-3), two benzene rings are clearly shown. These two benzene rings are X Ｃ That is, X represented by formula (C-3) corresponds to the above-mentioned "aromatic ring (c)". Ｃ is a divalent organic group containing at least two benzene rings. Ｃ５ Suitable examples of the substituent represented by X Ｃ Among these, one or more selected from a halogen atom, an alkyl group, an aryl group, and an arylalkyl group are more preferred, 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 are even more preferred.

[0095] In formula (C-3), nc3 and nc4 each independently represent an integer of 0 to 4, preferably 0 to 3, more preferably 0 to 2, and even more preferably 0 or 1.

[0096] In formula (C-3), R Ｃ４ represents a single bond or a divalent linking group selected from the group consisting of a divalent hydrocarbon group having 1 to 10 carbon atoms which may have a substituent, an oxygen atom, a sulfonyl group, a carbonyl group, a carbonate group, and combinations thereof. Ｃ４The divalent linking group represented by the formula (I) preferably has 1 to 30 carbon atoms, more preferably 1 to 20 or 1 to 15 carbon atoms.

[0097] R Ｃ４ The divalent hydrocarbon group in R, including its preferred examples, Ｃ１ Among them, an alkylene group having 1 to 6 carbon atoms which may have a substituent, a cycloalkylene group having 6 to 10 carbon atoms which may have a substituent, or an arylene group having 6 to 10 carbon atoms which may have a substituent is preferred. １ ~C ６ Alkylene-C ６ ~C １０ Arylene-C １ ~C ６ Alkylene group, C １ ~C ６ Alkylene-C ６ ~C １０ Arylene-C ６ ~C １０ Arylene-C １ ~C ６ In the case of a divalent group formed by a combination of these, the alkylene group or arylene group may have a suitable range of carbon atoms, and the divalent group may have a substituent, as described above. Suitable examples of the substituent are also shown in R Ｃ１ The same applies to the divalent hydrocarbon group in the above formula.

[0098] In view of being able to enjoy the effects of the present invention more effectively in combination with the divalent group represented by formula (C-1), X represented by formula (C-3) is particularly preferred. Ｃ An example is shown below.

[0099] In one preferred embodiment, in formula (C-3), R Ｃ４ represents a single bond, or a divalent group selected from an alkylene group having 1 to 6 carbon atoms which may have a substituent, a cycloalkylene group having 6 to 10 carbon atoms which may have a substituent, an arylene group having 6 to 10 carbon atoms which may have a substituent, or a combination thereof; R Ｃ５each independently represents a halogen atom, an alkyl group, an aryl group, or an arylalkyl group; nc3 and nc4 each independently represent 0 or 1.

[0100] In a more preferred embodiment, in formula (C-3), R Ｃ４ represents a single bond, an alkylene group having 1 to 3 carbon atoms which may have a substituent, or a cycloalkylene group having 6 to 10 carbon atoms which may have a substituent, R Ｃ５ each independently represents a fluorine atom, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 10 carbon atoms, or an arylalkyl group having 7 to 12 carbon atoms; and nc3 and nc4 each independently represent 0 or 1.

[0101] In formula (C-4), one naphthalene ring is clearly shown. This one naphthalene ring is X Ｃ That is, X represented by formula (C-4) corresponds to the above-mentioned "aromatic ring (c)". Ｃ is a divalent organic group containing one naphthalene ring. Ｃ６ Suitable examples of the substituent represented by X Ｃ Among these, one or more selected from a halogen atom, an alkyl group, an aryl group, and an arylalkyl group are more preferred, 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 are even more preferred.

[0102] In formula (C-4), each nc5 independently represents an integer of 0 to 4, preferably 0 to 3, and more preferably 0 to 2.

[0103] From the viewpoint of being able to enjoy the effects of the present invention more effectively in combination with the divalent group represented by formula (C-1), X represented by formula (C-4) is particularly preferred. Ｃ An example is shown below.

[0104] In one preferred embodiment, in formula (C-4), R Ｃ６each independently represents a halogen atom, an alkyl group, an aryl group, or an arylalkyl group; and each nc5 independently represents an integer of 0 to 4.

[0105] In a more preferred embodiment, in formula (C-4), R Ｃ６ each independently represents a fluorine atom, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 10 carbon atoms, or an arylalkyl group having 7 to 12 carbon atoms; and each nc5 independently represents an integer of 0 to 4.

[0106] Regardless of whether it is the general formula (1-1) or the general formula (1-2), n represents an integer of 1 or more. As described above, the aromatic oxycarbonyl compound of the present invention is an aromatic oxycarbonyl compound having X at least one group containing a divalent group represented by formula (C-1). Ｃ And, X Ｂ By containing a structural unit which is an oligomer unit of the above, when combined with an epoxy resin, a cured product can be obtained which exhibits excellent dielectric properties and good heat resistance. Furthermore, a cured product can be obtained which is excellent in smear removal during via hole formation and can suppress the haloing phenomenon. From the viewpoint of further enjoying the effects of the present invention, the upper limit of n is preferably 10 or less or 8 or less, more preferably 6 or less. Therefore, in a preferred embodiment, n represents an integer of 1 to 6.

[0107] From the viewpoint of being able to enjoy the effects of the present invention more effectively, the X per molecule of the aromatic oxycarbonyl compound of the present invention is Ｃ is the number of divalent groups represented by formula (C-1), and nC1 is the number of divalent groups represented by formula (C-1), the ratio of nC1 to nC [nC1 / nC] is preferably 0.2 or more, more preferably 0.3 or more or 0.4 or more, and even more preferably 0.5 or more, 0.6 or more, 0.7 or more, or 0.8 or more. The upper limit of this ratio is not particularly limited, and may be 1 (i.e., when all X Ｃ may be a divalent group represented by formula (C-1)) may be 0.95 or less, 0.9 or less, etc.

[0108] From the viewpoint of being able to enjoy the effects of the present invention even more, it is preferable that X per molecule of the aromatic oxycarbonyl compound of the present invention Ｃis the number of divalent groups represented by formula (C-2), and nC2 is the number of divalent groups represented by formula (C-2), the ratio of nC2 to nC [nC2 / nC] is preferably 0.2 or more, more preferably 0.3 or more or 0.4 or more, and even more preferably 0.5 or more, 0.6 or more, 0.7 or more, or 0.8 or more. The upper limit of this ratio is not particularly limited, and may be 1 (i.e., when all X Ｃ may be a divalent group represented by formula (C-2)) may be 0.95 or less, 0.9 or less, etc.

[0109] From the viewpoint of being able to enjoy the effects of the present invention more effectively, the X per molecule of the aromatic oxycarbonyl compound of the present invention is Ａ１ or X Ａ２ The number of nA, X Ｂ The number of nB, X Ｃ Let nC be the number of X Ａ１ , X Ａ２ , X Ｂ and X Ｃ When the number of groups containing a fused polycyclic aromatic ring is n', the ratio of n' to the total of nA, nB, and nC [n' / (nA+nB+nC)] is preferably greater than 0.2, more preferably 0.3 or greater, 0.4 or greater, or 0.5 or greater, and even more preferably greater than 0.5, 0.52 or greater, or 0.53 or greater. The upper limit of this ratio is not particularly limited and may be 1, but may also be, for example, 0.9 or less, 0.8 or less, or less than 0.8.

[0110] In the aromatic oxycarbonyl compound of the present invention, the equivalent weight of the aromatic ring oxycarbonyl group (active ester group equivalent weight) is preferably 180 g / eq. or more, more preferably 190 g / eq. or more, and even more preferably 200 g / eq. or more, or 210 g / eq. or more. The upper limit of the equivalent weight of the aromatic ring oxycarbonyl group can be, for example, 1000 g / eq. or less, 750 g / eq. or less, 700 g / eq. or less, 600 g / eq. or less, or 500 g / eq. or less.

[0111] From the viewpoint of use as a curing agent for an epoxy resin in a resin composition, 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. The lower limit of Mn is not particularly limited as long as the compound has the desired structure containing the divalent group represented by formula (C-1) above, and may be, for example, 400 or more, 500 or more, or 600 or more. The Mn of the aromatic oxycarbonyl compound of the present invention can be measured as a polystyrene-equivalent value by gel permeation chromatography (GPC). The preferred range of Mn is based on the value measured according to the method described in the section (GPC measurement conditions) below.

[0112] From the viewpoint of providing a cured product that exhibits exceptionally good dielectric properties and heat resistance in combination with an epoxy resin, the aromatic oxycarbonyl compound of the present invention is preferably a compound represented by general formula (1-1).

[0113] Examples of compounds represented by general formula (1-1) that are particularly suitable in combination with an epoxy resin from the viewpoint of providing a cured product that exhibits both exceptionally good dielectric properties and heat resistance are shown below.

[0114] In a particularly preferred embodiment, in general formula (1-1), X Ａ１ are each independently a monovalent group represented by the above formula (A-1) or (A-2) (R Ａ１ , R Ａ２ , na1, and na2 are the same as above, including preferred embodiments and ranges; Ｂ each independently represents a divalent group obtained by removing two hydrogen atoms from a monocyclic aromatic carbocyclic ring which may have one or more substituents selected from a halogen atom, an alkyl group, an aryl group, and an arylalkyl group; X Ｃ each independently represents a divalent organic group containing two or more monocyclic aromatic carbocyclic rings, or a divalent organic group containing at least one fused polycyclic aromatic carbocyclic ring, Ｃ is a divalent group represented by the above formula (C-2) (R Ｃ２ , R Ｃ３, nc1 and nc2 are the same as above, including preferred embodiments and ranges; and n represents an integer of 1 or more and 6 or less.

[0115] In an even more preferred embodiment, in the general formula (1-1), X Ａ１ are each independently a monovalent group represented by the above formula (A-1) or (A-2) (wherein R Ａ１ is at least one 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; R Ａ２ represents one 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, na1 is 0 or 1, and na2 is 0 or 1; Ｂ represents a divalent group formed by removing two hydrogen atoms from an unsubstituted monocyclic aromatic carbocyclic ring; X Ｃ each independently represent a divalent organic group containing two or more benzene rings (preferably a divalent group obtained by removing two hydroxy groups from a bisphenol compound which may have one or more substituents selected from a halogen atom, an alkyl group, an aryl group, and an arylalkyl group, or a divalent group obtained by removing two hydroxy groups from a dihydroxybiphenyl compound which may have one or more substituents selected from a halogen atom, an alkyl group, an aryl group, and an arylalkyl group), or a divalent organic group containing at least one naphthalene ring (preferably a divalent group obtained by removing two hydroxy groups from a dihydroxynaphthalene compound which may have one or more substituents selected from a halogen atom, an alkyl group, an aryl group, and an arylalkyl group, or a divalent group obtained by removing two hydroxy groups from a bisnaphthol compound which may have one or more substituents selected from a halogen atom, an alkyl group, an aryl group, and an arylalkyl group), Ｃ is a divalent group represented by the above formula (C-2) (wherein R Ｃ３represents a hydrogen atom or a monovalent aromatic group which may have one or more substituents selected from an alkyl group having 1 to 6 carbon atoms and an aryl group having 6 to 10 carbon atoms, and nc1 and nc2 are 0; and n represents an integer of 1 or more and 6 or less.

[0116] An example of the synthesis procedure for the aromatic oxycarbonyl compound of the present invention will be shown below.

[0117] In one embodiment, the aromatic oxycarbonyl compound of the present invention is a condensation reaction product of: (x1) a divalent aromatic hydroxy compound containing at least a compound represented by the following general formula (x1); (x2) a divalent aromatic carboxylic acid compound or a divalent aromatic carboxylic acid halide compound; and (x3) a monovalent aromatic hydroxy compound, or a monovalent aromatic carboxylic acid compound or a monovalent carboxylic acid halide compound.

[0118] (In the formula, R Ｃ１ , R Ｃ２ , nc1 and nc2 are the same as above.)

[0119] -(x1) Divalent Aromatic Hydroxy Compound- The component (x1) is a divalent aromatic hydroxy compound containing at least a compound represented by the above general formula (x1). By using the component (x1), an aromatic oxycarbonyl compound containing a bisnaphthol skeleton can be synthesized.

[0120] In synthesizing a suitable aromatic oxycarbonyl compound containing a bisnaphthol skeleton represented by formula (C-2), a divalent aromatic hydroxy compound containing at least a compound represented by the following general formula (x1-1) may be used as the component (x1):

[0121] (In the formula, R Ｃ２ , R Ｃ３ , nc1 and nc2 are the same as above.)

[0122] The compound represented by the general formula (x1) is an addition condensation reaction product of (x1a) an optionally substituted naphthol and (x1b) an aldehyde compound.

[0123] Therefore, in one embodiment, the method for producing an aromatic oxycarbonyl compound of the present invention includes: (1) a step of obtaining a divalent aromatic hydroxy compound represented by general formula (x1) by a condensation reaction between (x1a) an optionally substituted naphthol and (x1b) an aldehyde compound; and (2) a step of condensing the obtained divalent aromatic hydroxy compound, (x2) a divalent aromatic carboxylic acid compound or a divalent aromatic carboxylic acid halide compound, and (x3) a monovalent aromatic hydroxy compound, or a monovalent aromatic carboxylic acid compound or a monovalent carboxylic acid halide compound.

[0124] The naphthol (x1a) which may have a substituent is, for example, a naphthol having a substituent such as X in the target aromatic oxycarbonyl compound. Ｃ Any naphthol compound may be used to achieve the structure: Ｃ Suitable examples of the naphthol compound are as described above. For example, the naphthol compound may be a naphthol compound represented by the formula (C-2) described above. Ｃ Optionally substituted 2-naphthol can be used as the compound that provides the structure of X represented by formula (C-2) in which nc1 and nc2 are 0. Ｃ Unsubstituted 2-naphthol may be used as the compound that results in the structure of R Ｃ２ is an alkyl group, and nC1 and nC2 are 1. Ｃ To obtain the above structure, a monoalkyl-substituted 2-naphthol may be used.

[0125] The aldehyde compound (x1b) is a compound selected from the group consisting of X in the target aromatic oxycarbonyl compound and X Ｃ Any aldehyde compound may be used to achieve the structure of Ｃ１ is an alkylene group which may have a substituent; Ｃ As a compound that provides the structure of the formula (C-2-1), an alkyl aldehyde compound that may have a substituent may be used. Ｃ Formaldehyde may be used as a compound that provides the structure of X represented by the above formula (C-2-2).Ｃ Benzaldehyde may be used as the compound that provides the structure of X represented by the above formula (C-2-3). Ｃ 4-phenyl-benzaldehyde may be used as the compound that provides the structure of X represented by the above formula (C-2-4). Ｃ 4-methyl-benzaldehyde may be used as the compound that provides the structure of X represented by the above formula (C-2-5). Ｃ 4-propyl-benzaldehyde may be used as the compound that provides the structure of X represented by the above formula (C-2-6). Ｃ 1,4,6-trimethyl-benzaldehyde may be used as the compound that provides the structure of X represented by the above formula (C-2-7). Ｃ 1-Naphthaldehyde may be used as the compound that provides the structure of X represented by the above formula (C-2-8). Ｃ 2-Naphthaldehyde may be used as the compound that provides the structure shown below.

[0126] A compound represented by general formula (x1) (hereinafter also referred to as "divalent aromatic hydroxy compound (x1)") can be synthesized by an addition condensation reaction between the component (x1a) and the component (x1b). Depending on whether the component (x1a) used is a 1-naphthol compound or a 2-naphthol compound, R in the divalent aromatic hydroxy compound (x1) can be Ｃ１ That is, when a 2-naphthol compound is used, the bonding position of R Ｃ１ is bonded to the 1-carbon atom of the naphthalene ring (and thus the structure represented by formula (C-2)). Ｃ１ is bonded to the 2-position carbon and / or the 4-position carbon of the naphthalene ring, and in this case, the divalent aromatic hydroxy compound (x1) can be oligomerized. Ｃ has a structure represented by formula (C-2), and it is preferable to use a compound represented by formula (x1-1) as the divalent aromatic hydroxy compound (x1). Therefore, it is more preferable to use a 2-naphthol compound as the component (x1a).

[0127] The hydroxyl equivalent of the divalent aromatic hydroxy compound (x1) thus synthesized is preferably 400 g / eq. or less, more preferably 350 g / eq. or less, 300 g / eq. or less, 250 g / eq. or less, 240 g / eq. or less, 220 g / eq. or less, or 200 g / eq. or less. The lower limit of the hydroxyl equivalent can be, for example, 150 g / eq. or more.

[0128] After the reaction, the divalent aromatic hydroxy compound (x1) may be purified and dried. For example, after the condensation reaction, purification treatments such as water washing and microfiltration may be performed to remove by-product salts and excess starting materials from the system. Specifically, the (x1) component precipitated after the condensation reaction may be filtered, washed multiple times with water or an organic solvent such as toluene, and then subjected to a purification treatment of filtering again. The component (x1) may then be subjected to a drying treatment in which the water or organic solvent such as toluene is removed to obtain the component (x1) as a solid. However, the present inventors have found that, from the viewpoint of realizing an aromatic oxycarbonyl compound that, when combined with an epoxy resin, provides a cured product exhibiting both even better dielectric properties and heat resistance, it is preferable to subject a product containing the divalent aromatic hydroxy compound (x1) obtained by the addition condensation reaction of the components (x1a) and (x1b) to a condensation reaction with the components (x2) and (x3) without subjecting it to the above-mentioned purification and drying treatments. This is presumably because purification and drying oxidize the divalent aromatic hydroxy compound (x1), deteriorating the structure and physical properties of the resulting divalent aromatic hydroxy compound (x1) and, ultimately, the aromatic oxycarbonyl compound. In a preferred embodiment, a product containing the divalent aromatic hydroxy compound (x1) obtained by subjecting an optionally substituted naphthol (x1a) and an aldehyde compound (x1b) to an addition condensation reaction in the presence of an organic solvent is subjected to a condensation reaction with components (x2) and (x3) without purification or drying (i.e., in liquid form). The type of organic solvent may be the same as that described below for the condensation reaction of components (x1), (x2), and (x3).

[0129] The component (x1) may contain other divalent aromatic hydroxy compounds, as long as it contains at least the compound represented by the general formula (x1). Ｃ Any other divalent aromatic hydroxy compound may be used to achieve the structure of X represented by the above formula (C-3). Ｃ Examples of compounds that can provide the structure include biphenyl compounds and various bisphenol compounds. Examples of bisphenol compounds include bisphenol A, bisphenol F, bisphenol AF, bisphenol AP, bisphenol B, bisphenol BP, bisphenol C, and bisphenol M. Examples of divalent aromatic hydroxy compounds include X represented by the above-mentioned formula (C-4). Ｃ Examples of compounds that can produce the structure shown above include diols in which two hydroxy groups are bonded to the carbon atoms on the naphthalene ring (e.g., 2,7-naphthalenediol, 1,4-naphthalenediol, 1,5-naphthalenediol, 1,6-naphthalenediol, and 2,6-naphthalenediol). These divalent aromatic hydroxy compounds can be used to produce the desired aromatic oxycarbonyl compound with X Ｃ However, when it has a substituent, a divalent aromatic hydroxy compound having the substituent may be used.

[0130] —(x2) Divalent Aromatic Carboxylic Acid (Halide) Compound— The component (x2) is a divalent aromatic carboxylic acid compound or a divalent aromatic carboxylic acid halide compound, and is represented by the following formula (x2).

[0131] (In the formula, X Ｂ is the same as above, and Y represents a hydroxy group or a halogen atom.

[0132] The component (x2) is X in the target aromatic oxycarbonyl compound. Ｂ Any divalent aromatic carboxylic acid (halide) compound may be used depending on X Ｂ Suitable examples of X in the target aromatic oxycarbonyl compound are as described above. ＢWhen is a phenylene group which may have a substituent, isophthalic acid (chloride) which may have a substituent or terephthalic acid (chloride) which may have a substituent may be used.

[0133] —(x3) Monovalent Aromatic Hydroxy Compound or Monovalent Aromatic Carboxylic Acid (Halide) Compound— The component (x3) is a monovalent aromatic hydroxy compound represented by the following formula (x3-1), or a monovalent aromatic carboxylic acid compound or a monovalent aromatic carboxylic acid halide compound represented by the following formula (x3-2).

[0134] (In the formula, X Ａ１ , X Ａ２ and Y are the same as above.)

[0135] When producing an aromatic oxycarbonyl compound represented by formula (1-1), a monovalent aromatic hydroxy compound (x3-1) may be reacted with a combination of components (x1) and (x2).

[0136] The component (x3-1) is X in the target aromatic oxycarbonyl compound. Ａ１ Any aromatic monool may be used depending on X Ａ１ Suitable examples of the aromatic monool are as described above. For example, the aromatic monool may be a compound selected from the group consisting of X in the target aromatic oxycarbonyl compound, Ａ１ When X is an optionally substituted naphthyl group, an optionally substituted naphthol may be used. Ａ１ When is an optionally substituted phenyl group, an optionally substituted phenol may be used.

[0137] When producing an aromatic oxycarbonyl compound represented by formula (1-2), a monovalent aromatic carboxylic acid compound or a monovalent aromatic carboxylic acid halide compound (x3-2) may be reacted with a combination of the components (x1) and (x2).

[0138] The component (x3-2) is X in the target aromatic oxycarbonyl compound. Ａ２Any aromatic monocarboxylic acid (halide) compound may be used depending on the X Ａ２ Suitable examples of the aromatic monocarboxylic acid (halide) compound are as described above. For example, the aromatic monocarboxylic acid (halide) compound may be a compound selected from the group consisting of X in the target aromatic oxycarbonyl compound, Ａ２ When X is an optionally substituted naphthyl group, an optionally substituted naphthalenecarboxylic acid (halide) may be used. Ａ２ When is an optionally substituted phenyl group, an optionally substituted benzoic acid (halide) may be used.

[0139] In the condensation reaction of the components (x1), (x2), and (x3), condensation (esterification) proceeds between the components (x1) and (x2). In addition, when the component (x3-1) is used as the component (x3), condensation also occurs between the component (x3) and the component (x2). In addition, when the component (x3-2) is used as the component (x3), condensation also occurs between the component (x3) and the component (x1). In such a reaction, by changing the conditions such as the ratio of the amounts of each component, the degree of condensation between the components (x1) and (x2) can be adjusted, and the structure (repeating number n) of the resulting aromatic oxycarbonyl compound can be controlled.

[0140] The condensation reaction may be carried out in a solvent-free system without using a solvent, or in an organic solvent system using an organic solvent. Examples of organic solvents used in the condensation reaction include ketone-based solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone; acetate-based solvents such as ethyl acetate, butyl acetate, cellosolve acetate, propylene glycol monomethyl ether acetate, and carbitol acetate; carbitol-based solvents such as cellosolve and butyl carbitol; aromatic hydrocarbon solvents such as toluene and xylene; and amide-based solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methyl-2-pyrrolidone. The organic solvents may be used alone or in combination of two or more.

[0141] A base may be used in the condensation reaction. Examples of the base include alkali metal hydroxides such as sodium hydroxide (caustic soda) and potassium hydroxide; and tertiary amines such as triethylamine, pyridine, and N,N-dimethyl-4-aminopyridine (DMAP). The base may be used alone or in combination of two or more.

[0142] In the condensation reaction, a condensing agent and a phase transfer catalyst may be used, and any known condensing agent or phase transfer catalyst that can be used in an esterification reaction may be used.

[0143] The reaction temperature in the condensation reaction is not particularly limited as long as the condensation reaction proceeds, and may be, for example, in the range of 0 to 80° C. The reaction time in the condensation reaction is not particularly limited as long as the desired structure of the aromatic oxycarbonyl compound is achieved, and may be, for example, in the range of 30 minutes to 8 hours.

[0144] The aromatic oxycarbonyl compound may be purified after the condensation reaction. For example, after the condensation reaction, a purification step such as washing with water or microfiltration may be carried out to remove by-product salts and excess starting materials from the system. Specifically, after the condensation reaction, an amount of water necessary to dissolve the by-product salts is added, and the mixture is allowed to stand and separated, and the aqueous layer is discarded. If necessary, an acid is further added for neutralization, and water washing is repeated. Thereafter, the mixture is subjected to a dehydration step using a chemical or azeotropic method, and then subjected to microfiltration to remove impurities and purify. If necessary, the organic solvent is removed by distillation to obtain the aromatic oxycarbonyl compound. The organic solvent may also be used as a solvent for the resin composition as is, without completely removing the organic solvent.

[0145] The aromatic oxycarbonyl compound of the present invention, when combined with an epoxy resin, can provide a cured product exhibiting both excellent dielectric properties and good heat resistance, thereby achieving the low transmission loss and heat resistance required for 5G applications. The present inventors have also confirmed that the aromatic oxycarbonyl compound of the present invention, when combined with an epoxy resin, can provide a cured product that is excellent in smear removal during via hole formation and can suppress the halo phenomenon. Therefore, in a preferred embodiment, the aromatic oxycarbonyl compound of the present invention can be suitably used as an epoxy resin curing agent.

[0146] [Resin Composition] A resin composition can be produced using the aromatic oxycarbonyl compound of the present invention, and the present invention also provides such a resin composition.

[0147] The resin composition of the present invention comprises an aromatic oxycarbonyl compound and an epoxy resin, and the aromatic oxycarbonyl compound is the aromatic oxycarbonyl compound of the present invention, i.e., the above-described X having at least a bisnaphthol skeleton. Ｃ And, X Ｂ The present invention is characterized in that the aromatic oxycarbonyl compound contains a structural unit which is an oligomer unit of

[0148] X Ａ , X Ｂ , X Ｃ The details of the aromatic oxycarbonyl compound, including the preferred structure and the preferred range of the oxycarbonyl group equivalent, are as explained above in the section [Aromatic oxycarbonyl compound].

[0149] In the resin composition of the present invention, the type of epoxy resin is not particularly limited as long as it has one or more (preferably two or more) epoxy groups per molecule. Examples of epoxy resins include bisphenol A type epoxy resins, bisphenol F type epoxy resins, bisphenol S type epoxy resins, bisphenol AF type epoxy resins, phenol novolac type epoxy resins, tert-butyl-catechol type epoxy resins, naphthol type epoxy resins, naphthalene type epoxy resins, naphthylene ether type epoxy resins, glycidylamine type epoxy resins, glycidyl ester type epoxy resins, cresol novolac type epoxy resins, biphenyl type epoxy resins, phenol aralkyl type epoxy resins, biphenyl aralkyl type epoxy resins, fluorene skeleton type epoxy resins, dicyclopentadiene type epoxy resins, anthracene type epoxy resins, linear aliphatic epoxy resins, epoxy resins having a butadiene structure, alicyclic epoxy resins, heterocyclic epoxy resins, spiro ring-containing epoxy resins, cyclohexanedimethanol type epoxy resins, trimethylol type epoxy resins, and halogenated epoxy resins. The resin composition of the present invention, which contains a specific aromatic oxycarbonyl compound, can provide a cured product exhibiting both excellent dielectric properties and good heat resistance, regardless of the type of epoxy resin. In addition, in the resin composition of the present invention, the epoxy resin may be used alone or in combination of two or more types.

[0150] Epoxy resins can be classified into epoxy resins that are liquid at a temperature of 20°C (hereinafter referred to as "liquid epoxy resins") and epoxy resins that are solid at a temperature of 20°C (hereinafter referred to as "solid epoxy resins"). The resin composition of the present invention may contain only liquid epoxy resins as epoxy resins, only solid epoxy resins, or a combination of liquid and solid epoxy resins. When a combination of liquid and solid epoxy resins is contained, the blending ratio (liquid:solid) may be in the range of 20:1 to 1:20 (preferably 10:1 to 1:10, more preferably 3:1 to 1:3) by mass.

[0151] The epoxy group equivalent of the epoxy resin is preferably 50 g / eq. to 2000 g / eq., more preferably 60 g / eq. to 1000 g / eq., and even more preferably 80 g / eq. to 500 g / eq. The epoxy group equivalent is the mass of the epoxy resin containing one equivalent of epoxy groups, and can be measured in accordance with JIS K7236.

[0152] 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 Mw of the epoxy resin can be measured by the GPC method as a polystyrene-equivalent value.

[0153] In the resin composition of the present invention, the mass ratio of the aromatic oxycarbonyl compound to the epoxy resin (aromatic oxycarbonyl compound / epoxy resin) may be preferably 0.8 or more, more preferably 0.9 or more, and even more preferably 0.92 or more, 0.94 or more, or 0.95 or more. The upper limit of this mass ratio may be, for example, 2 or less, 1.9 or less, or 1.8 or less. Therefore, in one embodiment, the mass ratio of the aromatic oxycarbonyl compound to the epoxy resin is 0.8 to 2.

[0154] In the resin composition of the present invention, the total content of the aromatic oxycarbonyl compound and the epoxy resin is preferably 50% by mass or more, more preferably 60% by mass or more, and even more preferably 70% by mass or more, 75% by mass or more, or 80% by mass or more, based on 100% by mass of the resin components in the resin composition, from the viewpoint of providing a cured product exhibiting both excellent dielectric properties and good heat resistance. The upper limit of this total content is not particularly limited, but may be, for example, 98% by mass or less, 96% by mass or less, or 95% by mass or less.

[0155] In the present invention, the term "resin component" in relation to the resin composition refers to the non-volatile components constituting the resin composition excluding the inorganic filler described below.

[0156] The resin composition of the present invention may further contain a thermosetting resin other than an epoxy resin (hereinafter also referred to as "other thermosetting resins"). Examples of the other thermosetting resin include known resins used in forming insulating layers of circuit boards and sealing layers of semiconductor chip packages, such as benzocyclobutene resins, epoxy acrylate resins, urethane acrylate resins, urethane resins, cyanate resins, polyimide resins, benzoxazine resins, unsaturated polyester resins, and melamine resins.

[0157] The resin composition of the present invention may further contain a radically polymerizable resin. The type of radically polymerizable resin is not particularly limited as long as it has one or more (preferably two or more) radically polymerizable unsaturated groups per molecule, and known resins used in forming insulating layers of circuit boards and sealing layers of semiconductor chip packages may be used. Examples of radically polymerizable resins include resins having one or more radically polymerizable unsaturated groups selected from maleimide groups, vinyl groups, allyl groups, styryl groups, vinylphenyl groups, acryloyl groups, methacryloyl groups, fumaroyl groups, and maleoyl groups. In particular, from the viewpoint of being able to produce a cured product with exceptionally excellent dielectric properties in combination with the aromatic oxycarbonyl compound of the present invention, the radically polymerizable resin preferably contains one or more selected from maleimide resins, (meth)acrylic resins, and styryl resins.

[0158] 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-pyrrol-1-yl groups) in one molecule. Examples of maleimide resins include maleimide resins containing an aliphatic skeleton having 36 carbon atoms derived from dimer diamine, 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 indane skeleton, as described in the Japan Institute of Invention and Innovation Disclosure Technical Bulletin No. 2020-500211; and 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 Daiwa Kasei Co., Ltd.), and "BMI-80" (manufactured by Keiai Kasei Co., Ltd.).

[0159] The (meth)acrylic resin is not particularly limited in type, and may be a monomer or oligomer, as long as it has one or more (preferably two or more) (meth)acryloyl groups in one molecule. Here, the term "(meth)acryloyl group" is a general term for acryloyl groups and methacryloyl groups. Examples of methacrylic resins include (meth)acrylic resins such as "A-DOG" (manufactured by Shin-Nakamura Chemical 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.).

[0160] The styryl resin is not particularly limited in type, and may be a monomer or oligomer, as long as it has one or more (preferably two or more) styryl groups or vinylphenyl groups in one molecule. Examples of the styryl resin include styryl resins such as "OPE-2St," "OPE-2St 1200," and "OPE-2St 2200" (all manufactured by Mitsubishi Gas Chemical Company, Inc.).

[0161] When the resin composition of the present invention further contains the above-mentioned other thermosetting resins and / or radically polymerizable resins, the content thereof may be appropriately determined within a range that does not impair the effects of the present invention, and when the resin component in the resin composition is taken as 100% by mass, it may be preferably less than 40% by mass, less than 30% by mass, less than 25% by mass, less than 20% by mass, less than 15% by mass, or less than 10% by mass. 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, etc.

[0162] The resin composition of the present invention may further contain an inorganic filler, which can further reduce the linear thermal expansion coefficient and the dielectric loss tangent.

[0163] Examples of inorganic fillers include silica, alumina, barium sulfate, talc, clay, mica powder, aluminum hydroxide, magnesium hydroxide, calcium carbonate, magnesium carbonate, magnesium oxide, boron nitride, aluminum borate, barium titanate, strontium titanate, calcium titanate, magnesium titanate, bismuth titanate, titanium oxide, barium zirconate, and calcium zirconate. Among these, silica is preferred. Examples of silica include amorphous silica, fused silica, crystalline silica, synthetic silica, and hollow silica. Furthermore, spherical silica is preferred. The inorganic fillers may be used alone or in combination of two or more.

[0164] Examples of commercially available inorganic fillers include "SP60-05" and "SP507-05" manufactured by Nippon Steel Chemical & Material Co., Ltd.; "YC100C", "YA050C", "YA050C-MJE", "YA010C", "SC2500SQ", "SO-C4", "SO-C2", and "SO-C1" manufactured by Admatechs Co., Ltd.; "UFP-30", "DAW-03", and "FB-105FD" manufactured by Denka Co., Ltd.; "Silfil NSS-3N", "Silfil NSS-4N", and "Silfil NSS-5N" manufactured by Tokuyama Corporation; and "CellSpheres" and "MGH-005" manufactured by Taiheiyo Cement Corporation.

[0165] The average particle size of the inorganic filler is preferably 5 μm or less, more preferably 3 μm or less, even more preferably 2 μm or less, 1 μm or less, or 0.7 μm or less, from the viewpoint of reducing the surface roughness of the cured product (insulating layer) and facilitating the formation of fine wiring. The lower limit of the average particle size is not particularly limited, but is preferably 0.01 μm or more, more preferably 0.05 μm or more, even more preferably 0.07 μm or more, 0.1 μm or more, or 0.2 μm or more. The average particle size of the inorganic filler can be measured by a laser diffraction / scattering method based on Mie scattering theory. Specifically, the particle size distribution of the inorganic filler is created on a volume basis using a laser diffraction / scattering particle size distribution analyzer, and the median diameter is used as the average particle size. A measurement sample can be prepared by weighing 100 mg of inorganic filler and 10 g of methyl ethyl ketone into a vial and dispersing it ultrasonically for 10 minutes. The measurement sample was measured using a laser diffraction particle size distribution analyzer, with blue and red light source wavelengths used and a flow cell system to measure the volumetric particle size distribution of the inorganic filler, and the average particle size was calculated as the median diameter from the obtained particle size distribution. An example of a laser diffraction particle size distribution analyzer is the "LA-960" manufactured by Horiba, Ltd.

[0166] The inorganic filler is preferably one that has been surface-treated with a surface treatment agent such as an aminosilane coupling agent, a ureidosilane coupling agent, an epoxysilane coupling agent, a mercaptosilane coupling agent, a vinylsilane coupling agent, a styrylsilane coupling agent, an acrylatesilane coupling agent, an isocyanatesilane coupling agent, a sulfidesilane coupling agent, an organosilazane compound, or a titanate coupling agent to improve its moisture resistance and dispersibility.

[0167] When the resin composition of the present invention contains an inorganic filler, the content of the inorganic filler in the resin composition may be determined depending on the properties required of the resin composition, but when the non-volatile components in the resin composition are taken as 100 mass%, it is, for example, 5 mass% or more, 10 mass% or more, preferably 30 mass% or more, more preferably 40 mass% or more, and even more preferably 50 mass% or more. The upper limit of the content of the inorganic filler is not particularly limited, but can be, for example, 95 mass% or less, 90 mass% or less, etc.

[0168] The resin composition of the present invention may further contain an epoxy resin curing agent other than the aromatic oxycarbonyl compound (hereinafter also referred to as "other epoxy resin curing agent").

[0169] Other epoxy resin hardeners include "TD2090" and "TD2131" (manufactured by DIC Corporation), "MEH-7600", "MEH-7851", and "MEH-8000H" (manufactured by Meiwa Kasei Co., Ltd.), "NHN", "CBN", "GPH-65", and "GPH-103" (manufactured by Nippon Kayaku Co., Ltd.), "SN170", "SN180", "SN190", "SN475", "SN485", "SN495", "SN375", and "SN395" (manufactured by Nippon Steel Chemical & Material Co., Ltd.), "LA7052", and "LA70 phenol-based curing agents such as "54," "LA3018," and "LA1356" (manufactured by DIC Corporation); benzoxazine-based curing agents such as "Fa" and "P-d" (manufactured by Shikoku Chemicals Corporation) and "HFB2006M" (manufactured by Showa Polymer Co., Ltd.); acid anhydride-based curing agents such as methylhexahydrophthalic anhydride, methyl nadic anhydride, and hydrogenated methyl nadic anhydride; cyanate ester-based curing agents such as PT30, PT60, and BA230S75 (manufactured by Arxada); and benzoxazine-based curing agents.

[0170] When the resin composition of the present invention contains another epoxy resin curing agent, the content of the other epoxy resin curing agent in the resin composition may be determined depending on the properties required of the resin composition. When the resin component in the resin composition is taken as 100% by mass, the content is preferably 30% by mass or less, more preferably 20% by mass or less, and even more preferably 10% by mass or less, and the lower limit can be 0.01% by mass or more, 0.05% by mass or more, 0.1% by mass or more, etc.

[0171] The resin composition of the present invention may further contain a curing accelerator, which allows for efficient adjustment of the curing time and curing temperature.

[0172] Examples of the curing accelerator include organic phosphine compounds such as "TPP", "TPP-K", "TPP-S", and "TPTP-S" (manufactured by Hokko Chemical Industry Co., Ltd.); imidazole compounds such as "Curesol 2MZ", "2E4MZ", "Cl1Z", "Cl1Z-CN", "Cl1Z-CNS", "Cl1Z-A", "2MZ-OK", "2MA-OK", and "2PHZ" (manufactured by Shikoku Chemical Industry Co., Ltd.); amine adduct compounds such as Novacure (manufactured by Asahi Kasei Corporation) and Fujicure (manufactured by Fuji Chemical Industry Co., Ltd.); amine compounds such as 1,8-diazabicyclo[5,4,0]undecene-7,4-dimethylaminopyridine, benzyldimethylamine, 2,4,6-tris(dimethylaminomethyl)phenol, and 4-dimethylaminopyridine; and organometallic complexes or organometallic salts of cobalt, copper, zinc, iron, nickel, manganese, tin, and the like.

[0173] When the resin composition of the present invention contains a curing accelerator, the content of the curing accelerator in the resin composition may be determined depending on the properties required of the resin composition, but when the resin component in the resin composition is taken as 100% by mass, it is preferably 10% by mass or less, more preferably 5% by mass or less, and even more preferably 1% by mass or less, and the lower limit may be 0.001% by mass or more, 0.01% by mass or more, 0.05% by mass or more, etc.

[0174] The resin composition of the present invention may further contain any additives. Examples of such additives include organic fillers such as rubber particles; radical polymerization initiators such as peroxide radical polymerization initiators and azo radical polymerization initiators; thermoplastic resins such as phenoxy resins, polyvinyl acetal resins, polysulfone resins, polyethersulfone resins, polyphenylene ether resins, polyetheretherketone resins, and polyester resins; organometallic compounds such as organic copper compounds, organic zinc compounds, and organic cobalt compounds; colorants such as phthalocyanine blue, phthalocyanine green, iodine green, diazo yellow, crystal violet, titanium oxide, and carbon black; polymerization inhibitors such as hydroquinone, catechol, pyrogallol, and phenothiazine; leveling agents such as silicone leveling agents and acrylic polymer leveling agents; thickeners such as bentone and montmorillonite; antifoaming agents such as silicone antifoaming agents, acrylic antifoaming agents, fluorine-based antifoaming agents, and vinyl resin antifoaming agents; benzotriazole. 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 depending on the properties required for the resin composition.

[0175] The resin composition of the present invention may further contain an organic solvent as a volatile component. Examples of the organic solvent include ketone solvents such as acetone, methyl ethyl ketone (MEK), methyl isobutyl ketone, and cyclohexanone; ester solvents such as methyl acetate, ethyl acetate, butyl acetate, isobutyl acetate, isoamyl acetate, methyl propionate, ethyl propionate, and γ-butyrolactone; ether solvents such as tetrahydropyran, tetrahydrofuran, 1,4-dioxane, diethyl ether, diisopropyl ether, dibutyl ether, and diphenyl ether; alcohol solvents such as methanol, ethanol, propanol, butanol, and ethylene glycol; 2-ethoxyethyl acetate, propylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, ethyl diglycol acetate, γ-butyrolactone, and methoxypropionic acid. ether ester solvents such as methyl lactate; ester alcohol solvents such as methyl lactate, ethyl lactate, and methyl 2-hydroxyisobutyrate; ether alcohol solvents such as 2-methoxypropanol, 2-methoxyethanol, 2-ethoxyethanol, propylene glycol monomethyl ether, and diethylene glycol monobutyl ether (butyl carbitol); amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methyl-2-pyrrolidone; sulfoxide solvents such as dimethyl sulfoxide; nitrile solvents such as acetonitrile and propionitrile; aliphatic hydrocarbon solvents such as hexane, cyclopentane, cyclohexane, and methylcyclohexane; and aromatic hydrocarbon solvents such as benzene, toluene, xylene, ethylbenzene, and trimethylbenzene. The organic solvent may be used alone or in combination of two or more.

[0176] When the resin composition of the present invention contains an organic solvent, the content of the organic solvent in the resin composition may be determined depending on the properties required of the resin composition, and when all components in the resin composition are taken as 100% by mass, the content may 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.

[0177] The resin composition of the present invention can be prepared by appropriately mixing the necessary components among the above-mentioned components, and kneading or mixing them as needed using a kneading means such as a three-roll mill, a ball mill, a bead mill, or a sand mill, or a stirring means such as a super mixer or a planetary mixer.

[0178] The resin composition of the present invention, which contains a specific aromatic oxycarbonyl compound in combination with an epoxy resin, can provide a cured product that exhibits both excellent dielectric properties and good heat resistance.

[0179] In one embodiment, the cured product of the resin composition of the present invention is characterized by a low dielectric constant (Dk). For example, when measured at 5.8 GHz and 23°C as described in the "Dielectric Properties" section below, the dielectric constant (Dk) of the cured product of the resin composition of the present invention may be preferably 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.

[0180] In one embodiment, the cured product of the resin composition of the present invention is characterized by a low dielectric dissipation factor (Df). For example, when measured at 5.8 GHz and 23°C as described in the "Dielectric Properties" section below, the dielectric dissipation factor (Df) of the cured product of the resin composition of the present invention may be preferably 0.01 or less, 0.008 or less, 0.006 or less, 0.005 or less, 0.004 or less, 0.0035 or less, 0.0034 or less, 0.0032 or less, 0.003 or less, 0.0028 or less, or 0.0027 or less.

[0181] In one embodiment, the cured product of the resin composition of the present invention is characterized by high heat resistance. For example, when measured using a dynamic viscoelasticity measuring device under the conditions of a load of 200 mN and a heating rate of 2°C / min as described in the "Heat Resistance" section below, the glass transition temperature (Tg) may be preferably 130°C or higher, 140°C or higher, 145°C or higher, 150°C or higher, 155°C or higher, or 160°C or higher.

[0182] As described above, the resin composition of the present invention can produce a cured product exhibiting both excellent dielectric properties and good heat resistance, thereby achieving the 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 an insulating layer of a 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 an interlayer insulating layer of a printed wiring board). The resin composition of the present invention can also be suitably used when the printed wiring board is a circuit board with built-in components. The resin composition of the present invention can also be suitably used as a resin composition for a rewiring formation layer (resin composition for a rewiring formation layer) as an insulating layer for forming a rewiring layer in a semiconductor chip package, i.e., for forming an insulating layer of a rewiring substrate of a semiconductor chip package (insulating layer of a rewiring substrate). In the present invention, printed wiring boards and rewiring substrates are collectively referred to as "circuit boards," and therefore the resin composition of the present invention can be suitably used for an insulating layer of a circuit board.

[0183] The resin composition of the present invention can also be suitably used as a resin composition for encapsulating a semiconductor chip in a semiconductor chip package (a resin composition for encapsulating a semiconductor).

[0184] The resin composition of the present invention can also be used in a wide range of applications requiring a resin composition, such as sheet-like laminate materials such as resin sheets and prepregs, solder resists, underfill materials, die bonding materials, hole filling resins, and component embedding resins.

[0185] [Sheet-like Laminated Material (Resin Sheet, Prepreg)] The resin composition of the present invention can be used as it is, but may also be used in the form of a sheet-like laminated material containing the resin composition.

[0186] As the sheet-like laminate material, the following resin sheets and prepregs are preferred.

[0187] In one embodiment, the resin sheet includes a support and a layer of a resin composition (hereinafter simply referred to as a "resin composition layer") provided on the support, and is characterized in that the resin composition layer is formed from the resin composition of the present invention.

[0188] The thickness of the resin composition layer varies depending on the application, and may be appropriately determined depending on the application. For example, from the viewpoint of thinning printed wiring 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.

[0189] Examples of the support include a thermoplastic resin film, a metal foil, and a release paper, and a thermoplastic resin film or a metal foil is preferred. Therefore, in a preferred embodiment, the support is a thermoplastic resin film or a metal foil.

[0190] When a thermoplastic resin film is used as the support, examples of the thermoplastic resin include polyesters such as polyethylene terephthalate (PET) and polyethylene naphthalate (PEN), acrylics such as polycarbonate (PC) and polymethyl methacrylate (PMMA), cyclic polyolefins, triacetyl cellulose (TAC), polyether sulfide (PES), polyether ketone, polyimide, etc. Among these, polyethylene terephthalate and polyethylene naphthalate are preferred, and inexpensive polyethylene terephthalate is particularly preferred.

[0191] When a metal foil is used as the support, examples of the metal foil include copper foil and aluminum foil, with copper foil being preferred. The copper foil may be a foil made of a single metal, such as copper, or a foil made of an alloy of copper and another metal (e.g., tin, chromium, silver, magnesium, nickel, zirconium, silicon, titanium, etc.).

[0192] The support may be subjected to a matte treatment, a corona treatment, or an antistatic treatment on the surface that will be bonded to the resin composition layer. Alternatively, a support with a release layer, which has a release layer on the surface that will be bonded to the resin composition layer, may be used as the support. Examples of the release agent 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. Commercially available products may be used as the support with a release layer. Examples include "SK-1," "AL-5," and "AL-7" manufactured by Lintec Corporation, "Lumirror T60" manufactured by Toray Industries, Inc., "Purex" manufactured by Teijin Limited, and "Uni-Peel" manufactured by Unitika Ltd., which are PET films having a release layer primarily composed of an alkyd resin-based release agent.

[0193] 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 a support with a release layer is used, it is preferable that the thickness of the entire support with a release layer is in the above range.

[0194] When a metal foil is used as the support, a metal foil with a support substrate may be used, which is a thin metal foil with a peelable support substrate attached thereto. 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 a metal foil with a support substrate is used as the support, the resin composition layer is provided on the metal foil.

[0195] In the metal foil with a supporting substrate, the material of the supporting substrate is not particularly limited, and examples thereof include copper foil, aluminum foil, stainless steel foil, titanium foil, copper alloy foil, etc. When copper foil is used as the supporting substrate, it may be electrolytic copper foil or rolled copper foil. Furthermore, the release layer is not particularly limited as long as it can release the metal foil from the supporting substrate, and examples thereof include an alloy layer of an element selected from the group consisting of Cr, Ni, Co, Fe, Mo, Ti, W, and P; an organic coating, etc.

[0196] In the metal foil with a supporting substrate, the material of the metal foil is preferably, for example, copper foil or copper alloy foil.

[0197] In the metal foil with a supporting substrate, the thickness of the supporting substrate is not particularly limited, but is preferably in the range of 10 μm to 150 μm, 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.

[0198] In one embodiment, the resin sheet may further include an optional layer as needed. Examples of such optional layers include a protective film provided on the surface of the resin composition layer that is not bonded to the support (i.e., the surface opposite 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, adhesion of dust and the like to the surface of the resin composition layer and scratches can be suppressed.

[0199] The resin sheet can be produced, for example, by preparing a liquid resin composition as is or a resin varnish by dissolving the resin composition in an organic solvent, applying this onto a support using a die coater or the like, and then drying to form a resin composition layer.

[0200] The organic solvent may be the same as the organic solvent described as a component of the resin composition. The organic solvent may be used alone or in combination of two or more.

[0201] Drying may be carried out by known methods such as heating or hot air blowing. Drying conditions are not particularly limited, but drying is carried out so that the content of organic solvent in the resin composition layer becomes 10% by mass or less, preferably 5% by mass or less. Although this varies depending on the boiling point of the organic solvent in the resin composition or resin varnish, for example, when a resin composition or resin varnish containing 10% by mass to 60% by mass of organic solvent is used, the resin composition layer can be formed by drying at 50°C to 150°C for 3 to 10 minutes.

[0202] The resin sheet can be stored in a rolled state. When the resin sheet has a protective film, it can be used by peeling off the protective film.

[0203] In one embodiment, the prepreg is formed by impregnating a sheet-like fiber substrate with the resin composition of the present invention.

[0204] The sheet-like fiber 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 wiring boards and semiconductor chip packages, the thickness of the sheet-like fiber 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 fiber substrate is not particularly limited. It is usually 10 μm or more.

[0205] The prepreg can be produced by a known method such as a hot melt method or a solvent method.

[0206] The thickness of the prepreg may be in the same range as that of the resin composition layer in the resin sheet described above.

[0207] The sheet-like laminate material of the present invention can be suitably used to form an insulating layer of a printed wiring board (for an insulating layer of a printed wiring board), and more suitably used to form an interlayer insulating layer of a printed wiring board (for an interlayer insulating layer of a printed wiring board). The sheet-like laminate material of the present invention can also be suitably used to form an insulating layer of a rewiring board for a semiconductor chip package (for an insulating layer of a rewiring board). That is, the sheet-like laminate material of the present invention can be suitably used as an insulating layer for a circuit board. The sheet-like laminate material of the present invention can also be suitably used to encapsulate a semiconductor chip (for semiconductor encapsulation).

[0208] [Circuit Board] The resin composition of the present invention can be used to form an insulating layer for a circuit board. The present invention also provides such a circuit board, i.e., a circuit board including an insulating layer made of a cured product of the resin composition of the present invention.

[0209] <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 made of a cured product of the resin composition of the present invention.

[0210] The printed wiring board can be produced, for example, by using the above-mentioned resin sheet by a method including the following steps (I) and (II): (I) a step of laminating the resin sheet on an inner layer substrate so that the resin composition layer of the resin sheet is bonded to the inner layer substrate; and (II) a step of thermally curing the resin composition layer to form an insulating layer.

[0211] The "inner layer substrate" used in step (I) is a member that will become the substrate of a printed wiring board, and examples thereof include glass epoxy substrates, metal substrates, polyester substrates, polyimide substrates, BT resin substrates, and thermosetting polyphenylene ether substrates. The substrate may have a conductor layer on one or both sides, and this conductor layer may be patterned. An inner layer substrate having a conductor layer (circuit) formed on one or both sides of the substrate is sometimes referred to as an "inner layer circuit board." Furthermore, intermediate products on which an insulating layer and / or a conductor layer is to be further formed during the production of a printed wiring board are also included in the "inner layer substrate" of the present invention. When the printed wiring board is a circuit board with built-in components, an inner layer substrate with built-in components may be used.

[0212] The lamination of the inner layer substrate and the resin sheet can be carried out, for example, by thermocompression bonding the resin sheet to the inner layer substrate from the support side. Examples of a member for thermocompression bonding the resin sheet to the inner layer substrate (hereinafter also referred to as a "thermocompression bonding member") include a heated metal plate (such as a SUS panel) or a metal roll (such as a SUS roll). The thermocompression bonding member may be pressed directly onto the resin sheet, or may be pressed via an elastic material such as heat-resistant rubber so that the resin sheet can sufficiently conform to the surface irregularities of the inner layer substrate.

[0213] The 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 thermocompression temperature is preferably in the range of 60°C to 160°C, more preferably 80°C to 140°C, the thermocompression pressure is preferably in the range of 0.098 MPa to 1.77 MPa, more preferably 0.29 MPa to 1.47 MPa, and the thermocompression time is preferably in the range of 20 seconds to 400 seconds, more preferably 30 seconds to 300 seconds. The lamination may be carried out under reduced pressure conditions, preferably a pressure of 26.7 hPa or less.

[0214] The lamination can be performed using a commercially available vacuum laminator, such as a vacuum pressure laminator manufactured by Meiki Seisakusho Co., Ltd., a vacuum applicator manufactured by Nikko Materials Co., Ltd., or a batch-type vacuum pressure laminator.

[0215] After lamination, the laminated resin sheets may be smoothed under normal pressure (atmospheric pressure), for example, by pressing a thermocompression member from the support side. The pressing conditions for the smoothing treatment may be the same as the thermocompression conditions for lamination. The smoothing treatment may be performed using a commercially available laminator. Note that lamination and smoothing treatment may be performed consecutively using the commercially available vacuum laminator.

[0216] The support may be removed between step (I) and step (II), or may be removed after step (II). When a metal foil is used as the support, the conductor layer may be formed using the metal foil without peeling off the support. When a metal foil with a supporting substrate is used as the support, the supporting substrate (and the release layer) may be peeled off. Then, the conductor layer can be formed using the metal foil.

[0217] In step (II), the resin composition layer is thermally cured to form an insulating layer made of a cured product of the resin composition. The curing conditions for the resin composition layer are not particularly limited, and conditions typically employed for forming insulating layers for printed wiring boards may be used.

[0218] For example, the heat 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 is preferably 5 minutes to 240 minutes, more preferably 10 minutes to 150 minutes, and even more preferably 15 minutes to 120 minutes.

[0219] Before thermally curing the resin composition layer, the resin composition layer may be preheated at a temperature lower than the curing temperature. For example, prior to thermally 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.

[0220] When manufacturing a printed wiring board, the following steps may be further performed: (III) drilling holes in the insulating layer; (IV) roughening the insulating layer; and (V) forming a conductor layer. These steps (III) to (V) may be performed according to various methods known to those skilled in the art for use in manufacturing printed wiring boards. When the support is removed after step (II), the support may be removed 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 wiring board.

[0221] In another embodiment, the printed wiring board of the present invention can be produced using the above-mentioned prepreg. The production method is basically the same as when a resin sheet is used.

[0222] Step (III) is a step of drilling holes in the insulating layer, thereby forming holes such as via holes and through holes in the insulating layer. Step (III) may be performed using, for example, a drill, a laser, plasma, or the like, depending on the composition of the resin composition used to form the insulating layer. The dimensions and shape of the holes may be determined appropriately depending on the design of the printed wiring board.

[0223] Step (IV) is a step of roughening the insulating layer. Usually, in this step (IV), smear removal (desmear) is also performed. The procedure and conditions of the roughening treatment are not particularly limited, and known procedures and conditions that are usually used when forming an insulating layer of a printed wiring board can be adopted. For example, the insulating layer can be roughened by performing a swelling treatment with a swelling liquid, a roughening treatment with an oxidizing agent, and a neutralization treatment with a neutralizing liquid in this order.

[0224] The swelling liquid used in the roughening treatment is not particularly limited, but examples thereof include alkaline solutions and surfactant solutions, and is preferably an alkaline solution, with sodium hydroxide solution and potassium hydroxide solution being more preferred. Commercially available swelling liquids include "Swelling Dip Securigance P" and "Swelling Dip Securigance SBU" manufactured by Atotech Japan. The swelling treatment using a swelling liquid is not particularly limited, but can be carried out by, for example, immersing the insulating layer in a swelling liquid at 30°C to 90°C for 1 to 20 minutes. From the viewpoint of suppressing swelling of the resin in the insulating layer to an appropriate level, it is preferable to immerse the insulating layer in a swelling liquid at 40°C to 80°C for 5 to 15 minutes.

[0225] The oxidizing agent used in the roughening treatment is not particularly limited, but examples thereof include alkaline permanganate solutions prepared by dissolving potassium permanganate or sodium permanganate in an aqueous solution of sodium hydroxide. Roughening treatment using 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. The concentration of permanganate in the alkaline permanganate solution is preferably 5% by mass to 10% by mass. Commercially available oxidizing agents include alkaline permanganate solutions such as "Concentrate Compact CP" and "Dosing Solution Securigance P" manufactured by Atotech Japan.

[0226] The neutralizing solution used in the roughening treatment is preferably an acidic aqueous solution, and a commercially available product such as "Reduction Solution Securigant P" manufactured by Atotech Japan is an example.

[0227] The treatment with the neutralizing solution can be carried out by immersing the surface that has been roughened with an oxidizing agent in a neutralizing solution at 30° C. to 80° C. for 5 to 30 minutes. From the viewpoint of workability, etc., a method in which the object that has been roughened with an oxidizing agent is immersed in a neutralizing solution at 40° C. to 70° C. for 5 to 20 minutes is preferred.

[0228] Step (V) is a step of forming a conductor layer, and the conductor layer is formed on the insulating layer. The conductor material used for the conductor layer is not particularly limited. In a preferred embodiment, the conductor 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 conductor layer may be a single metal layer or an alloy layer. Examples of the alloy layer include layers formed from alloys of two or more metals selected from the above group (e.g., nickel-chromium alloys, copper-nickel alloys, and copper-titanium alloys). Among these, from the viewpoints of versatility in forming the conductor layer, cost, ease of patterning, etc., a single metal layer of chromium, nickel, titanium, aluminum, zinc, gold, palladium, silver, or copper, or an alloy layer of a nickel-chromium alloy, a copper-nickel alloy, or a copper-titanium alloy is preferred, a single metal layer of chromium, nickel, titanium, aluminum, zinc, gold, palladium, silver, or copper, or an alloy layer of a nickel-chromium alloy is more preferred, and a single metal layer of copper is even more preferred.

[0229] The conductor layer may have a single layer structure or a multi-layer structure in which two or more single metal layers or alloy layers made of different types of metals or alloys are stacked. When the conductor layer has a multi-layer structure, the layer in contact with the insulating layer is preferably a single metal layer of chromium, zinc, or titanium, or an alloy layer of a nickel-chromium alloy.

[0230] The thickness of the conductor layer depends on the desired design of the printed wiring board, but is generally 3 μm to 35 μm, preferably 5 μm to 30 μm.

[0231] 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 a conventionally known technique such as a semi-additive method or a full-additive method. From the viewpoint of ease of production, it is preferable to form the conductor layer by a semi-additive method. An example of forming the conductor layer by a semi-additive method will be described below.

[0232] First, a plating seed layer is formed on the surface of an 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 a metal layer is formed on the exposed plating seed layer by electrolytic plating, the mask pattern is removed. Thereafter, unnecessary plating seed layer is removed by etching or the like, thereby forming a conductor layer having the desired wiring pattern.

[0233] In another embodiment, the conductor layer may be formed using a metal foil. When a metal foil is used to form the conductor layer, it is preferable that step (V) be performed between step (I) and step (II). For example, after step (I), the support is removed, and a metal foil is laminated on the exposed surface of the resin composition layer. The lamination of the resin composition layer and the metal foil may be performed 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. Thereafter, a conductor layer having a desired wiring pattern can be formed using the metal foil on the insulating layer by a conventional known technique such as a subtractive method or a modified semi-additive method.

[0234] The metal foil can be produced by a known method such as an electrolytic method, a rolling method, etc. Examples of commercially available metal foils include HLP foil and JXUT-III foil manufactured by JX Nippon Mining & Smelting Corporation, and 3EC-III foil and TP-III foil manufactured by Mitsui Mining & Smelting Co., Ltd.

[0235] Alternatively, when a metal foil or a metal foil with a supporting substrate is used as the support for the resin sheet, the conductor layer may be formed using the metal foil, as described above.

[0236] <Rewiring Substrate for Semiconductor Chip Package> In one embodiment, the circuit board of the present invention is a rewiring substrate for a semiconductor chip package. Hereinafter, a method for manufacturing the semiconductor chip package will be described.

[0237] [Semiconductor Chip Package] 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. As described above, the semiconductor chip package of the present invention may also include an insulating layer (rewiring formation layer) of a rewiring substrate made of a cured product of the resin composition of the present invention.

[0238] A semiconductor chip package can be manufactured, for example, by a method including the following steps (1) to (6) using the resin composition and resin sheet of the present invention. The resin composition and resin sheet of the present invention can be used to form the sealing layer in step (3) or the rewiring formation layer in step (5). An example of forming a sealing layer or a rewiring formation layer using a resin composition or a resin sheet will be shown below. However, techniques for forming sealing layers and rewiring formation layers for semiconductor chip packages are known, and those skilled in the art can manufacture a semiconductor package using the resin composition and resin sheet of the present invention according to known techniques. (1) A step of laminating a temporary fixing film on a substrate; (2) A step of temporarily fixing a semiconductor chip on the temporary fixing film; (3) A step of forming a sealing layer on the semiconductor chip; (4) A step of peeling the substrate and the temporary fixing film from the semiconductor chip; (5) A step of forming a rewiring formation layer as an insulating layer on the surface of the semiconductor chip from which the substrate and the temporary fixing film have been peeled; and (6) A step of forming a rewiring layer as a conductor layer on the rewiring formation layer.

[0239] -Step (1)- The material used for the substrate is not particularly limited. Examples of the substrate include a silicon wafer, a glass wafer, a glass substrate, a metal substrate such as copper, titanium, stainless steel, or cold-rolled steel plate (SPCC), a substrate in which glass fiber is impregnated with an epoxy resin or the like and subjected to a thermosetting treatment (e.g., an FR-4 substrate), and a substrate made of bismaleimide triazine resin (BT resin).

[0240] The material of the temporary fixing film is not particularly limited as long as it can be peeled off from the semiconductor chip in step (4) and can temporarily fix the semiconductor chip. Commercially available products can be used as the temporary fixing film. Examples of commercially available products include Riva Alpha manufactured by Nitto Denko Corporation.

[0241] -Step (2)- The semiconductor chips can be temporarily fixed using known devices such as a flip chip bonder, a die bonder, etc. The layout and number of semiconductor chips to be arranged can be set appropriately depending on the shape and size of the temporary fixing film, the number of semiconductor packages to be produced, etc. For example, the semiconductor chips can be temporarily fixed by arranging them in a matrix of multiple rows and multiple columns.

[0242] -Step (3)- A resin composition layer of the resin sheet of the present invention is laminated on a semiconductor chip, or the resin composition of the present invention is applied to a semiconductor chip and cured (for example, thermally cured) to form a sealing layer.

[0243] 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 thermocompressing the resin sheet to the semiconductor chip from the support side. Examples of a member for thermocompressing the resin sheet to the semiconductor chip (hereinafter also referred to as a "thermocompression member") include a heated metal plate (such as a SUS panel) or a metal roll (such as a SUS roll). It is preferable to press the thermocompression member not directly onto the resin sheet, but via an elastic material such as heat-resistant rubber, so that the resin sheet can adequately conform to the surface irregularities of the semiconductor chip. The semiconductor chip and the resin sheet can also be laminated by a vacuum lamination method, and the lamination conditions and preferred ranges are the same as those described in connection with the method for manufacturing a printed wiring board.

[0244] After lamination, the resin composition is thermally cured to form the sealing layer under the same conditions as those described in relation to the method for producing a printed wiring board.

[0245] The support of the resin sheet may be peeled off after the resin sheet is laminated on the semiconductor chip and thermally cured, or the support may be peeled off before the resin sheet is laminated on the semiconductor chip.

[0246] When forming a sealing layer by applying the resin composition of the present invention, the application conditions are the same as the application conditions when forming the resin composition layer described in relation to the resin sheet of the present invention, and the preferred ranges are also the same.

[0247] -Step (4)- The method for peeling off the substrate and the temporary fixing film can be changed as appropriate depending on the material of the temporary fixing film, etc., and examples thereof include a method in which the temporary fixing film is heated and foamed (or expanded) to peel off, and a method in which ultraviolet light is irradiated from the substrate side to reduce the adhesive strength of the temporary fixing film and then peel it off.

[0248] In the method of heating and foaming (or expanding) the temporary fixing film to peel it off, the heating conditions are usually 100 to 250°C for 1 to 90 seconds or 5 to 15 minutes. In the method of irradiating ultraviolet light from the substrate side to reduce the adhesive strength of the temporary fixing film to peel it off, the irradiation dose of ultraviolet light is usually 10 mJ / cm. ２ ~1000mJ / cm ２ is.

[0249] Step (5)—The material for forming the rewiring formation layer (insulating layer) is not particularly limited as long as it has insulating properties when the rewiring formation layer (insulating layer) is formed, and from the viewpoint of ease of manufacturing the semiconductor chip package, ultraviolet-curable resins and thermosetting resins are preferred. The rewiring formation layer may be formed using the resin composition or resin sheet of the present invention.

[0250] After forming the redistribution layer, via holes may be formed in the redistribution layer to connect the semiconductor chip to a conductor layer (described later). The via holes may be formed by a known method depending on the material of the redistribution layer.

[0251] Step (6)—The formation of a conductor layer on the rewiring formation layer may be carried out in the same manner as step (V) described in relation to the method for producing a printed wiring board. Steps (5) and (6) may be repeated to alternately stack (build up) conductor layers (rewiring layers) and rewiring formation layers (insulating layers).

[0252] The manufacturing of the semiconductor chip package may further include steps of (7) forming a solder resist layer on the conductor layer (rewiring layer), (8) forming bumps, and (9) dicing the plurality of semiconductor chip packages into individual semiconductor chip packages. These steps may be performed according to various methods known to those skilled in the art for use in manufacturing semiconductor chip packages.

[0253] By forming an encapsulating layer and a rewiring formation layer using the resin composition and resin sheet of the present invention, which provide a cured product exhibiting excellent dielectric properties, a semiconductor chip package with extremely low transmission loss can be realized, regardless of whether the semiconductor package is a fan-in package or a fan-out package. In one embodiment, the semiconductor chip package of the present invention is a fan-out package. The resin composition and resin sheet of the present invention can be applied to both fan-out panel level packages (FO-PLPs) and fan-out wafer level packages (FO-WLPs). In one embodiment, the semiconductor package of the present invention is a fan-out panel level package (FOPLP). In another embodiment, the semiconductor package of the present invention is a fan-out wafer level package (FOWLP).

[0254] [Semiconductor Device] The semiconductor device of the present invention includes a layer made of a cured product of the resin composition of the present invention, and includes the circuit board or semiconductor chip package of the present invention.

[0255] Examples of semiconductor devices include various semiconductor devices used in electrical appliances (for example, computers, mobile phones, digital cameras, and televisions) and vehicles (for example, motorcycles, automobiles, trains, ships, and aircraft).

[0256] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples.

[0257] Example 1 Synthesis of aromatic oxycarbonyl compound (1) (1-1) Synthesis of 1,1'-methylenedi-2-naphthol (1x)

[0258] A four-necked round flask equipped with a stirrer, thermometer, and condenser was charged with 489.6 g (3.40 mol, reagent) of 2-naphthol, 2700 g of distilled water, and 37% aqueous formaldehyde solution (1.70 mol, reagent), and the mixture was heated to 80°C with stirring to form a suspension. 27.98 g (0.34 mol, reagent) of 49% aqueous sodium hydroxide solution was added dropwise over 30 minutes while maintaining the temperature at 80°C, and the mixture was then allowed to react at 80°C for 2 hours. An appropriate amount of hydrochloric acid was added to the resulting reaction solution to neutralize it, and the mixture was then filtered to obtain a precipitated solid. The resulting solid was washed twice with distilled water and then dried in an oven at 120°C under vacuum to obtain 460 g of a solid.

[0259] The hydroxyl equivalent of this solid was measured according to the following measurement method, and a value of 150 g / eq. (theoretical value 150 g / eq.) was obtained. Furthermore, the mass spectrum (negative ion mode) of this solid was measured according to the following measurement method, and a spectral peak at m / z = 299 was detected. Furthermore, measurements were performed by gel permeation chromatography (GPC) and infrared spectroscopy (IR) under the GPC measurement conditions and IR measurement conditions described below. From these analytical data, it was confirmed that the obtained solid was 1,1'-methylenedi-2-naphthol (1x) (hereinafter also referred to as "bisnaphthol (1x)") having the desired molecular structure, i.e., the above structure.

[0260] (Method for measuring hydroxyl group equivalent) According to JIS-K0070, the hydroxyl groups in 1,1'-methylenedi-2-naphthol were acetylated with acetic anhydride-pyridine, followed by hydrolysis, and the remaining acetic acid was back-titrated to quantify the hydroxyl group equivalent.

[0261] (Mass Spectrometry Conditions) A sample was diluted with THF to 1 mg / mL, and LC / MS was measured under the following conditions. HPLC: ACQUITY UPLC (Nihon Waters) MS: SQ Detector 2 (Nihon Waters) Column: ACQUITY UPLC BEH C8 1.7 μm, 2.1 mm × 50 mm (Nihon Waters) Mobile phase A: 2 mmol 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 (electrospray ionization) positive or negative Ion polarity: Positive detection mode or negative detection mode Desolvation gas flow rate: 700 L / hr, 250°C Cone gas: 70 L / hr Ion source heater: 150°C

[0262] (GPC measurement conditions) Measuring apparatus: "HLC-8420GPC" manufactured by Tosoh Corporation Column: Guard column "HXL-L" manufactured by Tosoh Corporation + "TSK-GEL Super HZ2000" manufactured by Tosoh Corporation + "TSK-GEL Super HZ2000" manufactured by Tosoh Corporation + "TSK-GEL Super HZ3000" manufactured by Tosoh Corporation + "TSK-GEL Super HZ4000" manufactured by Tosoh Corporation Detector: RI (differential refractometer) Data processing: "GPC workstation EcoSEC-WorkStation" manufactured by Tosoh Corporation 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", the following monodisperse polystyrene with a known molecular weight was used. TSKgel F-10, F-4, F-1, A-5000, A-1000, A-500 (manufactured by Tosoh Corporation) Sample: 10 μl of a tetrahydrofuran solution containing 0.2% by mass of resin solids filtered through a microfilter

[0263] (IR measurement conditions) Measurement device: "FT / IR-4600" manufactured by JASCO Corporation

[0264] (1-2) Esterification reaction: synthesis of aromatic oxycarbonyl compound (1)

[0265] A four-necked round flask equipped with a stirrer, thermometer, and condenser was charged with 72.00 g (0.24 mol) of bisnaphthol (1x) obtained in the above step (1-1), 97.44 g (0.48 mol, reagent) of isophthalic acid chloride, 69.12 g (0.48 mol, reagent) of 1-naphthol, 2.39 g of tetrabutylammonium bromide (reagent), and 350 g of toluene (reagent), in a composition ratio such that the n value in the theoretical structure shown in formula (1a) above was 1.0 and the active ester group equivalent was 212 g / eq., and the mixture was stirred while blowing in nitrogen gas to completely dissolve the mixture. At 30°C, 156.7 g (0.98 mol) of a 25% aqueous solution of caustic soda was added dropwise over 2 hours, while taking care to avoid heat generation, so that the temperature would ultimately rise to 60°C. After further stirring at 60°C for 2 hours, 100 g of distilled water was added and the mixture was allowed to stand for 20 minutes, and the lower by-product brine layer was discarded. The mixture was washed twice with the same amount of distilled water and purified, and then heated for azeotropic dehydration. The resulting solution was microfiltered to remove impurities, and toluene was distilled under reduced pressure at a maximum temperature of 200°C to obtain 181 g of solid matter.

[0266] The mass spectrum of the obtained solid was measured, and spectral peaks of m / z = 849 corresponding to the n=1 protonated product and m / z = 1279 corresponding to the n=2 protonated product were detected. Furthermore, GPC and IR analysis results confirmed that the obtained solid had the desired molecular structure, i.e., the structure of an aromatic oxycarbonyl compound containing a bisnaphthol skeleton according to the theoretical structure shown in formula (1a) above. The obtained aromatic oxycarbonyl compound is referred to as "aromatic oxycarbonyl compound (1)."

[0267] Example 2: Synthesis of aromatic oxycarbonyl compound (2)

[0268] A four-necked round flask equipped with a stirrer, thermometer, and condenser was charged with 69.12 g (0.48 mol, reagent) of 2-naphthol, 400 g of toluene, and 3.92 g (0.05 mol, reagent) of 49% aqueous sodium hydroxide solution, and the mixture was heated to 50°C to dissolve the components. 19.46 g (0.24 mol, reagent) of 37% aqueous formaldehyde solution was added dropwise over 30 minutes while maintaining the temperature at 50°C, and the mixture was then allowed to react at 80°C for 2 hours. The resulting reaction solution was neutralized by adding an appropriate amount of hydrochloric acid, and then heated to remove toluene and water by distillation until no more water was distilled off. Azeotropic dehydration was then performed to completely remove water. The product was then subjected to a condensation reaction in its liquid form without purification or drying. That is, the product was treated to obtain a product having an n value of 1.0 in the theoretical structure shown in formula (1a) above, and an active ester group equivalent of 212 g / eq. 97.44 g (0.48 mol, reagent) of isophthalic acid chloride, 69.12 g (0.48 mol, reagent) of 1-naphthol, 2.39 g (reagent) of tetrabutylammonium bromide, and 100 g of toluene (reagent) were charged in a composition ratio such that the following was achieved: 97.44 g (0.48 mol, reagent), 69.12 g (0.48 mol, reagent) of 1-naphthol, 2.39 g (reagent) of tetrabutylammonium bromide, and 100 g of toluene (reagent) were added, and the mixture was stirred while blowing in nitrogen gas to completely dissolve the mixture. At 30°C, 156.7 g (0.98 mol) of 25% aqueous caustic soda solution was added dropwise over a period of 2 hours, while paying attention to heat generation, so that the temperature would ultimately rise to 60°C. After that, stirring was continued for another 2 hours at 60°C, and then 100 g of distilled water was added and the mixture was allowed to stand for liquid separation, and the lower by-product brine layer was discarded. The same amount of distilled water was added and the mixture was washed and purified twice, after which it was heated and azeotropically dehydrated. The resulting solution was microfiltered to remove impurities, and then toluene was distilled under reduced pressure at a maximum temperature of 200°C, yielding 185 g of solids.

[0269] The mass spectrum of the obtained solid was measured, and spectral peaks of m / z = 849 corresponding to the n=1 protonated product and m / z = 1279 corresponding to the n=2 protonated product were detected. Furthermore, the results of GPC and IR analysis confirmed that the obtained solid had the desired molecular structure, i.e., the structure of an aromatic oxycarbonyl compound containing a bisphthol skeleton according to the theoretical structure shown in formula (1a) above. The obtained aromatic oxycarbonyl compound is referred to as "aromatic oxycarbonyl compound (2)."

[0270] Example 3: Synthesis of aromatic oxycarbonyl compound (3)

[0271] A four-necked round flask equipped with a stirrer, thermometer, dropping funnel, and nitrogen gas inlet was charged with 72.00 g (0.24 mol) of the bisnaphthol (1x), 73.08 g (0.36 mol, reagent) of isophthalic acid chloride, 34.56 g (0.24 mol, reagent) of 1-naphthol, 2.87 g of tetrabutylammonium bromide (reagent), and 350 g of toluene (reagent), in a composition ratio such that the n value in the theoretical structure shown in formula (2a) above was 2.0 and the active ester group equivalent was 213 g / eq. The mixture was stirred while blowing in nitrogen gas to completely dissolve the mixture. At 30°C, 115.2 g (0.72 mol) of a 25% aqueous solution of caustic soda was added dropwise over 2 hours, while taking care to avoid heat generation, so that the temperature would ultimately rise to 60°C. After further stirring at 60°C for 2 hours, 100 g of distilled water was added and the mixture was allowed to stand for 20 minutes, and the lower by-product brine layer was discarded. The same amount of distilled water was added twice for water washing and purification, and then the mixture was heated for azeotropic dehydration. The resulting solution was microfiltered to remove impurities, and toluene was distilled under reduced pressure at a maximum temperature of 200°C to obtain 139 g of solid matter.

[0272] The mass spectrum of the obtained solid was measured, and spectral peaks of m / z = 849 corresponding to the n=1 protonated product and m / z = 1279 corresponding to the n=2 protonated product were detected. Furthermore, GPC and IR analysis confirmed that the obtained solid had the desired molecular structure, i.e., the structure of an aromatic oxycarbonyl compound containing a bisnaphthol skeleton according to the theoretical structure shown in formula (2a) above. The obtained aromatic oxycarbonyl compound is referred to as "aromatic oxycarbonyl compound (3)."

[0273] Example 4: Synthesis of aromatic oxycarbonyl compound (4)

[0274] An operation was carried out in the same manner as in Example 1, except that in step (1-2) of Example 1, 81.60 g (0.48 mol, reagent) of 2-phenylphenol was used instead of 69.12 g (0.48 mol, reagent) of 1-naphthol, to obtain 195 g of a solid.

[0275] The mass spectrum of the obtained solid was measured, and spectral peaks of m / z = 902 corresponding to the n=1 protonated product and m / z = 1331 corresponding to the n=2 protonated product were detected. Furthermore, GPC and IR analysis results confirmed that the obtained solid had the desired molecular structure, i.e., the structure of an aromatic oxycarbonyl compound containing a bisnaphthol skeleton according to the theoretical structure shown in formula (3a) above. The obtained aromatic oxycarbonyl compound is referred to as "aromatic oxycarbonyl compound (4)."

[0276] Example 5: Synthesis of aromatic oxycarbonyl compound (5)

[0277] The same procedure as in Example 2 was repeated except that 81.60 g (0.48 mol, reagent) of 2-phenylphenol was used instead of 69.12 g (0.48 mol, reagent) of 1-naphthol, to obtain 199 g of a solid.

[0278] The mass spectrum of the obtained solid was measured, and spectral peaks of m / z = 902 corresponding to the n=1 protonated product and m / z = 1331 corresponding to the n=2 protonated product were detected. Furthermore, GPC and IR analysis confirmed that the obtained solid had the desired molecular structure, i.e., the structure of an aromatic oxycarbonyl compound containing a bisnaphthol skeleton according to the theoretical structure shown in formula (3a) above. The obtained aromatic oxycarbonyl compound is referred to as "aromatic oxycarbonyl compound (5)."

[0279] Example 6: Synthesis of aromatic oxycarbonyl compound (6)

[0280] The same procedure as in Example 3 was repeated except that 40.80 g (0.24 mol, reagent) of 2-phenylphenol was used instead of 34.56 g (0.24 mol, reagent) of 1-naphthol, to obtain 145 g of a solid.

[0281] The mass spectrum of the obtained solid was measured, and m / z=902 corresponding to the n=1 protonated product and m / z=1331 corresponding to the n=2 protonated product were detected. Furthermore, GPC and IR analysis results confirmed that the obtained solid had the desired molecular structure, i.e., the structure of an aromatic oxycarbonyl compound containing a bisnaphthol skeleton according to the theoretical structure shown in formula (4a) above. The obtained aromatic oxycarbonyl compound is referred to as "aromatic oxycarbonyl compound (6)."

[0282] Example 7 Synthesis of aromatic oxycarbonyl compound (7) (7-1) Synthesis of reaction product (2x) of 1-naphthol and formaldehyde 410 g of a solid was obtained in the same manner as in Example 1, except that 489.6 g (3.40 mol, reagent) of 1-naphthol was used instead of 489.6 g (3.40 mol, reagent) of 2-naphthol in step (1-1) of Example 1. GPC analysis confirmed that the obtained solid contained a plurality of oligomer components.

[0283] (7-2) Esterification reaction: synthesis of aromatic oxycarbonyl compound (7) 185 g of a solid was obtained in the same manner as in Example 1, except that 72.00 g (0.24 mol) of the bisnaphthol (1x) was replaced with 72.00 g (2x) of the reaction product of 1-naphthol and formaldehyde in step (1-2) of Example 1. The obtained solid, i.e., an aromatic oxycarbonyl compound containing an oligomerized bisnaphthol skeleton, is referred to as "aromatic oxycarbonyl compound (7)."

[0284] Example 8: Synthesis of aromatic oxycarbonyl compound (8) (8-1) Synthesis of reaction product (3x) of 1-naphthol and formaldehyde

[0285] A four-necked round flask equipped with a stirrer, a thermometer, and a condenser was charged with 200 g of the reaction product (2x) of 1-naphthol and formaldehyde obtained in step (7-1) of Example 7 and 600 g of toluene, and the mixture was heated under reflux to perform recrystallization. The obtained solid was washed twice with toluene and then dried in a vacuum oven at 120°C for 2 hours, yielding 150 g of a solid.

[0286] The hydroxyl equivalent of this solid was measured according to the above-mentioned measurement method, and a value of 151 g / eq. (theoretical value: 150 g / eq.) was obtained. The mass spectrum (negative ion mode) of this solid was measured, and a spectral peak at m / z = 299 was detected. Furthermore, measurements were carried out by GPC and IR. From these analytical data, it was confirmed that the obtained solid was bisnaphthol (3x) having the above structure, obtained by removing oligomer components from the reaction product (2x) of 1-naphthol and formaldehyde.

[0287] (8-2) Esterification reaction: synthesis of aromatic oxycarbonyl compound (8)

[0288] The same procedure as in Example 1 was repeated, except that in step (1-2) of Example 1, 72.00 g (0.24 mol) of bisnaphthol (3x) was used instead of 72.00 g (0.24 mol) of bisnaphthol (1x), to obtain 183 g of a solid.

[0289] The mass spectrum of the obtained solid was measured, and spectral peaks of m / z = 849 corresponding to the n=1 protonated product and m / z = 1279 corresponding to the n=2 protonated product were detected. Furthermore, GPC and IR analysis results confirmed that the obtained solid had the desired molecular structure, i.e., the structure of an aromatic oxycarbonyl compound containing a bisnaphthol skeleton according to the theoretical structure shown in formula (6a) above. The obtained aromatic oxycarbonyl compound is referred to as "aromatic oxycarbonyl compound (8)."

[0290] Example 9: Synthesis of aromatic oxycarbonyl compound (9)

[0291] A four-necked round flask equipped with a stirrer, thermometer, and condenser was charged with 120.00 g (0.40 mol) of the bisnaphthol (1x), 40.60 g (0.20 mol, reagent), 56.24 g (0.40 mol, reagent), 2.17 g (reagent) of tetrabutylammonium bromide, and 350 g (reagent) of toluene, in a composition ratio such that the n value in the theoretical structure shown in formula (7a) above was 1.0 and the active ester group equivalent was 235 g / eq. The mixture was stirred while blowing in nitrogen gas to completely dissolve the mixture. At 30°C, 128.0 g (0.80 mol) of a 25% aqueous solution of caustic soda was added dropwise over 2 hours, while taking care to avoid heat generation, so that the temperature would ultimately rise to 60°C. After further stirring at 60°C for 2 hours, 100 g of distilled water was added and the mixture was allowed to stand for 20 minutes, and the lower by-product brine layer was discarded. The same amount of distilled water was added twice for water washing and purification, and then the mixture was heated for azeotropic dehydration. The resulting solution was microfiltered to remove impurities, and toluene was distilled under reduced pressure at a maximum temperature of 200°C to obtain 158 g of solids.

[0292] The mass spectrum of the obtained solid was measured, and spectral peaks of m / z = 939 corresponding to the n=1 protonated product and m / z = 1370 corresponding to the n=2 protonated product were detected. Furthermore, GPC and IR analysis confirmed that the obtained solid had the desired molecular structure, i.e., the structure of an aromatic oxycarbonyl compound containing a bisnaphthol skeleton according to the theoretical structure shown in formula (7a) above. The obtained aromatic oxycarbonyl compound is referred to as "aromatic oxycarbonyl compound (9)."

[0293] Example 10: Synthesis of aromatic oxycarbonyl compound (10)

[0294] A four-necked round flask equipped with a stirrer, thermometer, and condenser was charged with 120.00 g (0.40 mol) of the bisnaphthol (1x), 40.60 g (0.20 mol, reagent) of isophthalic acid chloride, 76.25 g (0.40 mol, reagent) of 1-naphthoyl chloride, 2.37 g of tetrabutylammonium bromide (reagent), and 360 g of toluene (reagent), in a composition ratio such that the n value in the theoretical structure shown in formula (8a) above was 1.0 and the active ester group equivalent was 260 g / eq. The mixture was stirred while blowing in nitrogen gas to completely dissolve the mixture. At 30°C, 128.0 g (0.80 mol) of a 25% aqueous solution of caustic soda was added dropwise over a period of 2 hours, while taking care to avoid heat generation, so that the temperature would ultimately rise to 60°C. After further stirring at 60°C for 2 hours, 100 g of distilled water was added and the mixture was allowed to stand for 20 minutes, and the lower by-product brine layer was discarded. The mixture was washed twice with the same amount of distilled water and purified, and then heated for azeotropic dehydration. The resulting solution was microfiltered to remove impurities, and toluene was distilled under reduced pressure at a maximum temperature of 200°C to obtain 168 g of solid matter.

[0295] The mass spectrum of the obtained solid was measured, and spectral peaks of m / z = 1039 corresponding to the n=1 protonated product and m / z = 1470 corresponding to the n=2 protonated product were detected. Furthermore, GPC and IR analysis results confirmed that the obtained solid had the desired molecular structure, i.e., the structure of aromatic oxycarbonyl compound (10) containing a bisnaphthol skeleton according to the theoretical structure shown in formula (8a) above. The obtained aromatic oxycarbonyl compound is referred to as "aromatic oxycarbonyl compound (10)."

[0296] Example 11: Synthesis of aromatic oxycarbonyl compound (11)

[0297] A four-necked round flask equipped with a stirrer, thermometer, dropping funnel, and nitrogen gas inlet was charged with 108.00 g (0.35 mol) of the bisnaphthol (1x), 81.20 g (0.40 mol, reagent) of isophthalic acid chloride, 14.40 g (0.10 mol, reagent) of 1-naphthol, 2.04 g of tetrabutylammonium bromide (reagent), and 350 g of toluene (reagent), in a composition ratio such that the n value in the theoretical structure shown in formula (9a) above was 7.0 and the active ester group equivalent was 214 g / eq., and the mixture was stirred while blowing in nitrogen gas to completely dissolve the mixture. At 30°C, 128.00 g (0.80 mol) of a 25% aqueous solution of caustic soda was added dropwise over 2 hours, while taking care to avoid heat generation, so that the temperature would ultimately rise to 60°C. After further stirring at 60°C for 2 hours, 100 g of distilled water was added and the mixture was allowed to stand for 20 minutes, and the lower by-product brine layer was discarded. The same amount of distilled water was added twice for water washing and purification, and then the mixture was heated for azeotropic dehydration. The resulting solution was microfiltered to remove impurities, and toluene was distilled under reduced pressure at a maximum temperature of 200°C to obtain 155 g of solid matter.

[0298] The mass spectrum of the obtained solid was measured, and spectral peaks of m / z = 849 corresponding to the n=1 protonated product and m / z = 1279 corresponding to the n=2 protonated product were detected. Furthermore, GPC and IR analysis results confirmed that the obtained solid had the desired molecular structure, i.e., the structure of an aromatic oxycarbonyl compound containing a bisnaphthol skeleton according to the theoretical structure shown in formula (9a) above. The obtained aromatic oxycarbonyl compound is referred to as "aromatic oxycarbonyl compound (11)."

[0299] Example 12: Synthesis of aromatic oxycarbonyl compound (12) (12-1) Synthesis of reaction product (4x) of allylnaphthol and formaldehyde

[0300] 545 g of a solid was obtained in the same manner as in Example 1, except that 625.6 g (3.40 mol) of allyl 2-naphthol was used instead of 489.6 g (3.40 mol) of 2-naphthol in step (1-1) of Example 1. The hydroxyl equivalent of this solid was measured according to the above-mentioned measurement method, and a value of 191 g / eq. (theoretical value 190 g / eq.) was obtained. The mass spectrum (negative ion mode) of this solid was measured, and a spectral peak at m / z = 379 was detected. Furthermore, measurements were performed by GPC and IR. These analytical results confirmed that the solid was bisnaphthol (4x), a reaction product of allyl 2-naphthol and formaldehyde.

[0301] (12-2) Esterification reaction: synthesis of aromatic oxycarbonyl compound (12)

[0302] The procedure was repeated in the same manner as in Example 1, except that 91.20 g of the reaction product of allyl 2-naphthol and formaldehyde (4x) was used instead of 72.00 g (0.24 mol) of bisnaphthol (1x) in step (1-2) of Example 1, to obtain 195 g of a solid. The obtained solid, i.e., an aromatic oxycarbonyl compound containing a bisnaphthol skeleton, is referred to as "aromatic oxycarbonyl compound (12)."

[0303] Example 13: Synthesis of aromatic oxycarbonyl compound (13) (13-1) Synthesis of reaction product (5x) of 2-naphthol and benzaldehyde

[0304] 201.60 g (1.40 mol, reagent) of 2-naphthol, 440 g of 2-propanol, and 74.20 g (0.70 mol, reagent) of benzaldehyde were placed in a four-necked round flask equipped with a stirrer, thermometer, and condenser, and completely dissolved while stirring at room temperature. 13.44 g (0.14 mol, reagent) of methanesulfonic acid was added, and the mixture was allowed to react at room temperature for 48 hours. 200 g of 2-propanol was added to the resulting reaction solution, which was then filtered to obtain a precipitated solid. The resulting solid was washed twice with 2-propanol and then dried in an oven at 50°C under vacuum, yielding 210 g of solid.

[0305] The hydroxyl equivalent of this solid was measured according to the following measurement method, and a value of 186 g / eq. (theoretical value 188 g / eq.) was obtained. Furthermore, the mass spectrum (negative ion mode) of this solid was measured according to the following measurement method, and a spectral peak at m / z = 375 was detected. Furthermore, measurements were performed by gel permeation chromatography (GPC) and infrared spectroscopy (IR) under the following GPC measurement conditions and IR measurement conditions. From these analytical data, it was confirmed that the obtained solid was the desired molecular structure, i.e., bisnaphthol (5x) having the above structure.

[0306] (13-2) Esterification reaction: synthesis of aromatic oxycarbonyl compound (13)

[0307] A four-necked round flask equipped with a stirrer, thermometer, and condenser was charged with 90.36 g (0.24 mol) of bisnaphthol (5x) obtained in the above step (13-1), 97.44 g (0.48 mol, reagent) of isophthalic acid chloride, 69.12 g (0.48 mol, reagent) of 1-naphthol, 2.39 g of tetrabutylammonium bromide (reagent), and 600 g of toluene (reagent), in a composition ratio such that the n value in the theoretical structure shown in formula (11a) above was 1.0 and the active ester group equivalent was 231 g / eq., and the mixture was stirred while blowing in nitrogen gas to completely dissolve the mixture. At 30°C, 156.7 g (0.98 mol) of a 25% aqueous solution of caustic soda was added dropwise over 2 hours, while taking care to avoid heat generation, so that the temperature would ultimately rise to 60°C. After further stirring at 60°C for 2 hours, 100 g of distilled water was added and the mixture was allowed to stand for 20 minutes, and the lower by-product brine layer was discarded. The same amount of distilled water was added twice for water washing and purification, and then the mixture was heated for azeotropic dehydration. The resulting solution was microfiltered to remove impurities, and toluene was distilled under reduced pressure at a maximum temperature of 200°C to obtain 191 g of solid matter.

[0308] The mass spectrum of the obtained solid was measured, and spectral peaks of m / z = 925 corresponding to the n=1 protonated product and m / z = 1432 corresponding to the n=2 protonated product were detected. Furthermore, GPC and IR analysis confirmed that the obtained solid had the desired molecular structure, i.e., the structure of an aromatic oxycarbonyl compound containing a bisnaphthol skeleton according to the theoretical structure shown in formula (11a) above. The obtained aromatic oxycarbonyl compound is referred to as "aromatic oxycarbonyl compound (13)."

[0309] Example 14: Synthesis of aromatic oxycarbonyl compound (14)

[0310] The procedure of Example 13 was repeated, except that 81.60 g (0.48 mol, reagent) of 2-phenylphenol was used instead of 69.12 g (0.48 mol, reagent) of 1-naphthol in step (1-2) of Example 13, to obtain 195 g of a solid. The obtained solid, i.e., an aromatic oxycarbonyl compound containing a bisnaphthol skeleton, is referred to as "aromatic oxycarbonyl compound (14)."

[0311] Comparative Example 1: Synthesis of aromatic oxycarbonyl (C1)

[0312] In a four-necked round flask equipped with a stirrer, thermometer, and condenser, 68.72 g (0.24 mol) of 1,1'-bi-2-naphthol, 97.44 g (0.48 mol, reagent), 69.12 g (0.48 mol, reagent) of 1-naphthol, 2.39 g of tetrabutylammonium bromide (reagent), and 350 g of toluene (reagent) were charged in a composition ratio such that the n value in the theoretical structure shown in (c1a) above was 1.0 and the active ester group equivalent was 209 g / eq., and the mixture was stirred while blowing in nitrogen gas to completely dissolve it. At 30°C, 156.7 g (0.98 mol) of a 25% aqueous solution of caustic soda was added dropwise over 2 hours, taking care to avoid heat generation, so that the temperature would ultimately rise to 60°C. After further stirring at 60°C for 2 hours, 100 g of distilled water was added and the mixture was allowed to stand for 20 minutes, and the lower by-product brine layer was discarded. The same amount of distilled water was added twice for water washing and purification, and then the mixture was heated for azeotropic dehydration. The resulting solution was microfiltered to remove impurities, and toluene was distilled under reduced pressure at a maximum temperature of 200°C to obtain 180 g of solids.

[0313] The mass spectrum of the obtained solid was measured, and spectral peaks were detected at m / z = 835, corresponding to the protonated product with n = 1, and at m / z = 1251, corresponding to the protonated product with n = 2. Furthermore, the results of GPC and IR analysis confirmed that the obtained solid had the desired molecular structure, i.e., the structure of the aromatic oxycarbonyl compound (C1) containing a binaphthol skeleton according to the theoretical structure represented by the above formula (c1a).

[0314] Comparative Example 2: Synthesis of aromatic oxycarbonyl (C2)

[0315] In a four-necked round flask equipped with a stirrer, thermometer, and condenser, 114.53 g (0.40 mol) of 1,1'-bi-2-naphthol, 40.60 g (0.20 mol, reagent), 56.24 g (0.40 mol, reagent) of benzoyl chloride, 2.11 g (reagent) of tetrabutylammonium bromide, and 350 g (reagent) of toluene were charged in a composition ratio such that the n value in the theoretical structure shown in formula (c2a) above was 1.0 and the active ester group equivalent was 228 g / eq., and the mixture was stirred while blowing in nitrogen gas to completely dissolve it. 128.0 g (0.80 mol) of 25% aqueous caustic soda solution was added dropwise at 30 ° C. over 2 hours, while paying attention to heat generation, so that the temperature would ultimately rise to 60 ° C. After further stirring at 60°C for 2 hours, 100 g of distilled water was added and the mixture was allowed to stand for 20 minutes, and the lower by-product brine layer was discarded. The same amount of distilled water was added twice for water washing and purification, and then the mixture was heated for azeotropic dehydration. The resulting solution was microfiltered to remove impurities, and toluene was distilled under reduced pressure at a maximum temperature of 200°C to obtain 160 g of solid matter.

[0316] The mass spectrum of the obtained solid was measured, and spectral peaks were detected at m / z = 911, corresponding to the protonated product with n = 1, and at m / z = 1327, corresponding to the protonated product with n = 2. Furthermore, the results of GPC and IR analysis confirmed that the obtained solid had the desired molecular structure, i.e., the structure of an aromatic oxycarbonyl compound (C2) containing a bisnaphthol skeleton according to the theoretical structure shown in formula (c2a) above.

[0317] Examples 15 to 28 and Comparative Examples 3 and 4 (1) Preparation of Resin Compositions Each of the synthesized aromatic oxycarbonyl compounds (1) to (14), (C1), and (C2) was melt-mixed at 150° C. with a bisphenol A liquid epoxy resin (DIC Corporation, "850S," epoxy equivalent: 183 g / eq.) and a biphenylaralkyl epoxy resin (Nippon Kayaku Co., Ltd., "NC3000," epoxy equivalent: 275 g / eq.) according to the compositions shown in Table 1. 4-Dimethylaminopyridine (Koei Chemical Industry Co., Ltd., "DMAP") was then added to prepare a resin composition.

[0318] (2) Production of cured product The prepared resin composition was filled into a mold (100 mm × 100 mm × 0.5 mm) coated with a release agent and heat-cured at 150°C for 10 minutes to obtain a cured product. The cured product was removed from the mold and further heat-cured at 200°C for 3 hours to produce a sheet-like cured product.

[0319] (3) Evaluation of Cured Products The sheet-like cured products produced in Examples 15 to 28 and Comparative Examples 3 and 4 were subjected to evaluation tests in the following manner. The results are shown in Table 1.

[0320] [Dielectric Properties] The sheet-like cured product was cut into test pieces of a predetermined size, and the relative dielectric constant (Dk) and dielectric loss tangent (Df) were measured using a split cylinder resonator (EM Lab "CR-710") and a PNA microwave network analyzer (Keysight "N5227B") at a measurement frequency of 5.8 GHz and 23°C. For each cured product, measurements were taken on five test pieces (n=5), and the average value was calculated.

[0321] [Heat Resistance] The sheet-like cured product 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 Nano Technology Co., Ltd.) under the measurement conditions of a load of 200 mN and a heating rate of 2°C / min.

[0322]

[0323] Examples 29 to 42 and Comparative Examples 5 and 6 (1) Preparation of Resin Composition Varnish Each of the synthesized aromatic oxycarbonyl compounds (1) to (14), (C1), and (C2) was mixed with a bisphenol A liquid epoxy resin (DIC Corporation "850S", epoxy equivalent 183 g / eq.), a biphenylaralkyl epoxy resin (Nippon Kayaku Co., Ltd. "NC3000H", epoxy equivalent 291 g / eq.), 4-dimethylaminopyridine (Koei Chemical Co., Ltd. "DMAP"), a phenoxy resin (Mitsubishi Chemical Corporation "YL6954BH30"), spherical silica (Admatechs Co., Ltd. "SO-C2", average particle size 0.50 μm), methyl ethyl ketone (MEK), and cyclohexanone in the compositions shown in Table 2 to prepare a resin composition varnish.

[0324] (2) Preparation of Resin Sheet The prepared resin composition varnish was applied to a polyethylene terephthalate film (thickness 38 μm, hereinafter abbreviated as “PET film”) using a die coater so that the thickness of the resin composition layer after drying would be 40 μm, and the film was dried at 80° C. to 120° C. (average 100° C.) for 6 minutes to prepare a resin sheet.

[0325] (3) Production of Cured Product The resin sheet was heated at 190° C. for 120 minutes to thermally cure the resin composition layer. The PET film was then peeled off to obtain a sheet-like cured product.

[0326] (4) Evaluation of Cured Product The sheet-like cured product was subjected to evaluation tests in the following manner.

[0327] [Dielectric Properties] The sheet-like cured products produced in Examples 29 to 42 and Comparative Examples 5 and 6 were subjected to a dielectric property evaluation test in the same manner as in Examples 15 to 28 and Comparative Examples 3 and 4.

[0328] [Smear Removal] (Surface Treatment of Interior Substrate) A glass cloth-based epoxy resin double-sided copper-clad laminate (copper foil thickness: 18 μm, substrate thickness: 0.8 mm, Panasonic "R1515A") having copper foil on the surface was prepared as an inner layer substrate. The copper foil on the surface of this inner layer substrate was roughened by etching using a microetching agent (MEC "CZ8101") with a copper etching amount of 1 μm. The substrate was then dried at 190°C for 30 minutes.

[0329] (Lamination and curing of resin sheets) The resin sheets obtained in the examples and comparative examples were laminated on both sides of the inner layer substrate using a batch-type vacuum pressure laminator (a two-stage build-up laminator "CVP700" manufactured by Nikko Materials Co., Ltd.) so that the resin composition layer was bonded to the inner layer substrate. This lamination was performed by reducing the pressure for 30 seconds to 13 hPa or less, and then pressing at a temperature of 100°C and a pressure of 0.74 MPa for 30 seconds.

[0330] The laminated resin sheet was then heat-pressed at atmospheric pressure at 100°C and a pressure of 0.5 MPa for 60 seconds to smooth it. It was then placed in a 130°C oven and heated for 30 minutes, and then transferred to a 170°C oven and heated for 30 minutes. The heating cured the resin composition layer, resulting in an insulating layer containing a cured resin composition. Thus, the above procedure yielded an intermediate substrate having a layer structure of PET film / insulating layer / inner layer substrate / insulating layer / PET film.

[0331] (Via hole formation) Via Mechanics CO ２ The insulating layer was processed using a laser processing machine (LK-2K212 / 2C) to form via holes in the insulating layer. The processing was performed under the conditions of a frequency of 2000 Hz, a pulse width of 3 μs, an output of 0.95 W, and 3 shots. The formed via holes had a top diameter (diameter) of 50 μm on the surface of the insulating layer and a diameter of 40 μm on the bottom surface of the insulating layer. The top diameter refers to the diameter of the opening of the via hole. After that, the PET film was peeled off.

[0332] (Roughening Treatment) The intermediate substrate was immersed in a swelling solution, Swelling Dip Securigant P manufactured by Atotech Japan, at 60° C. for 10 minutes. Next, the intermediate substrate was immersed in a roughening solution, Concentrate Compact P (KMnO ４ The intermediate substrate was immersed in a neutralizing solution (Reduction Solution Securigant P manufactured by Atotech Japan) at 40° C. for 5 minutes. The obtained intermediate substrate was referred to as evaluation substrate A.

[0333] (Evaluation of smear removal ability) The periphery of the bottom of the via hole (via bottom) of evaluation substrate A was observed with a scanning electron microscope (SEM). From the image obtained by this observation, the maximum smear length from the wall surface of the bottom of the via hole was measured and evaluated according to the following criteria. The maximum smear length represents the length of the longest smear among the smears formed at the bottom of the via hole. "◯": Maximum smear length is less than 4 μm. "Δ": Maximum smear length is 4 μm or more and less than 5 μm. "X": Maximum smear length is 5 μm or more.

[0334] [Haloing] Evaluation substrate A was subjected to cross-sectional observation using an FIB-SEM composite device ("SMI3050SE" manufactured by SII Nanotechnology Inc.). Specifically, the insulating layer was scraped using an FIB (focused ion beam) so that a cross section parallel to the thickness direction of the insulating layer and passing through the center of the via bottom of the via hole was revealed. This cross section was observed using an SEM. The bottom diameter and top diameter of the via hole were measured from the observed image. The bottom diameter refers to the diameter of the bottom of the via hole, and the top diameter refers to the diameter of the opening of the via hole.

[0335] Furthermore, in the image observed by SEM, a gap formed by the insulating layer peeling off from the copper foil of the inner layer substrate was observed, continuing from the edge of the via bottom. From the observed image, the distance r1 from the center of the via bottom to the edge of the via bottom (corresponding to the inner radius of the gap) and the distance r2 from the center of the via bottom to the far end of the gap (corresponding to the outer radius of the gap) were measured, and the difference r2 - r1 between these distances r1 and r2 was calculated as the halo distance from the edge of the via bottom at that measurement point.

[0336] The above measurement was performed on five randomly selected via holes. The average of the top diameters of the five measured via holes was used as the top diameter Lt of the sample after the roughening treatment. The average of the bottom diameters of the five measured via holes was used as the bottom diameter Lb of the sample after the roughening treatment. Furthermore, the average of the halo distances of the five measured via holes was used as the halo distance Wb from the edge of the via bottom of the sample.

[0337] From the measurement results, the haloing ratio Hb (the ratio of the haloing distance Wb from the edge of the via bottom after the roughening treatment to the radius (Lb / 2) of the via bottom of the via hole after the roughening treatment, "Wb / (Lb / 2)") was calculated. If the haloing ratio Hb was 50% or less, it was judged as "◯", and if the haloing ratio Ht was greater than 50%, it was judged as "X".

[0338]

Claims

1. An aromatic oxycarbonyl compound represented by the following general formula (1-1) or general formula (1-2). (In the formula, X Ａ１ and X Ａ２ each independently represent a monovalent organic group containing at least one aromatic ring (a), X Ｂ each independently represent a divalent organic group containing at least one aromatic ring (b), X Ｃ each independently represent a divalent organic group containing at least one aromatic ring (c), where at least one X Ｃ represents a divalent group represented by the following formula (C-1), and n represents an integer of 1 or more.) (In the formula, R Ｃ１ represents a divalent organic group, R Ｃ２ each independently represent a halogen atom or an alkyl group, nc1 and nc2 each independently represent an integer of 0 to 6, and * represents a bond.) 2. The aromatic oxycarbonyl compound according to claim 1, wherein the divalent group represented by formula (C-1) is a divalent group represented by the following formula (C-2). (In the formula, R Ｃ２ , nc1 and nc2 are the same as above, and R Ｃ３ represents a hydrogen atom or a monovalent organic group, and * represents a bond.) 3. R Ｃ３ The aromatic oxycarbonyl compound according to claim 2, wherein R represents a hydrogen atom or a monovalent aromatic group which may have a substituent.

4. R Ｃ３ The aromatic oxycarbonyl compound according to claim 2, wherein R represents a hydrogen atom.

5. The aromatic oxycarbonyl compound according to claim 2, wherein nc1 and nc2 are 0.

6. The aromatic oxycarbonyl compound according to claim 1, wherein the aromatic ring (a) 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.

7. 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 a halogen atom, an alkyl group, an aryl group, and an arylalkyl group.

8. The aromatic oxycarbonyl compound according to claim 1, wherein the aromatic ring (c) 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.

9. The aromatic oxycarbonyl compound according to claim 1, wherein n represents an integer of 1 or more and 6 or less.

10. The aromatic oxycarbonyl compound according to claim 1, represented by formula (1-1).

11. The number of X per molecule of the aromatic oxycarbonyl compound Ａ１ or X Ａ２ is nA, the number of X Ｂ is nB, the number of X Ｃ is nC, and when the number of groups containing a condensed polycyclic aromatic ring among X Ａ１ , X Ａ２ , X Ｂ and X Ｃ is n', the ratio [n' / (nA + nB + nC)] of n' to the sum of nA, nB and nC is more than 0.

5. The aromatic oxycarbonyl compound according to claim 1.

12. The aromatic oxycarbonyl compound according to claim 1, which is a condensation reaction product of: (x1) a divalent aromatic hydroxy compound containing at least a compound represented by the following general formula (x1); (x2) a divalent aromatic carboxylic acid compound or a divalent aromatic carboxylic acid halide compound; and (x3) a monovalent aromatic hydroxy compound, or a monovalent aromatic carboxylic acid compound or a monovalent carboxylic acid halide compound. (In the formula, R Ｃ１ , R Ｃ２ are the same as defined above, and nc1 and nc2 are the same as defined above.) 13. (1) A step of obtaining a divalent aromatic hydroxy compound represented by the following general formula (x1) (hereinafter referred to as "divalent aromatic hydroxy compound (x1)") by a condensation reaction between naphthol which may have a substituent (x1a) and an aldehyde compound; and (2) A step of subjecting the obtained divalent aromatic hydroxy compound (x1) to a condensation reaction with a divalent aromatic carboxylic acid compound (x2), or a divalent aromatic carboxylic acid halide compound, and a monovalent aromatic hydroxy compound (x3), or a monovalent aromatic carboxylic acid compound or a monovalent carboxylic acid halide compound. A method for producing an aromatic oxycarbonyl compound. (In the formula, Ｃ１ R represents a divalent organic group, Ｃ２ R each independently represents a substituent, and nc1 and nc2 each independently represent an integer of 0 to 6.) 14. The method for producing an aromatic oxycarbonyl compound according to claim 13, wherein the obtained product containing the divalent aromatic hydroxy compound (x1) is subjected to a condensation reaction with (x2) a divalent aromatic carboxylic acid compound or a divalent aromatic carboxylic acid halide compound and (x3) a monovalent aromatic hydroxy compound, or a monovalent aromatic carboxylic acid compound or a monovalent carboxylic acid halide compound without being subjected to purification and drying treatments.

15. An epoxy resin curing agent containing the aromatic oxycarbonyl compound according to any one of claims 1 to 12.

16. A resin composition containing the aromatic oxycarbonyl compound according to any one of claims 1 to 12 and an epoxy resin.

17. The resin composition according to claim 16, further containing an inorganic filler.

18. The resin composition according to claim 16, further containing an organic solvent.

19. The resin composition according to claim 16, which is for an insulating layer of a circuit board.

20. The resin composition according to claim 16, which is for semiconductor encapsulation.

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

22. The resin sheet according to claim 21, wherein the support is a thermoplastic resin film or a metal foil.

23. A prepreg obtained by impregnating a sheet-like fiber base material with the resin composition according to claim 16.

24. The cured product of the resin composition according to claim 16.

25. A circuit board including an insulating layer made of the cured product of the resin composition according to claim 16.

26. A semiconductor chip package including a sealing layer made of the cured product of the resin composition according to claim 16.

27. The semiconductor chip package according to claim 26, which is a fan-out type package.

28. A semiconductor device including the circuit board according to claim 25.

29. A semiconductor device including the semiconductor chip package according to claim 26.

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