Resin composition, adhesive agent, sealing material, cured product, semiconductor device, and electronic component

Abstract

The present invention addresses the problem of providing: a resin composition which is at least photocurable or curable at low temperatures (for example, at 100°C or less), and which gives a cured product that has excellent high-temperature high-humidity reliability; an adhesive agent or a sealing material which contains the resin composition; a cured product of the resin composition; a semiconductor device which comprises the cured product; and an electronic component.　The present invention provides: a resin composition which contains (A) an alicyclic epoxy compound, (B) an oxetane compound, (C) a filler, and (D) an acid generator that is a salt which is composed of an anion represented by formula (1) (wherein R1, R2, R3, and R4 each independently represent an alkyl group having 1 to 18 carbon atoms or an aryl group having 6 to 14 carbon atoms, provided that at least one of R1, R2, R3, and R4 represents an aryl group having 6 to 14 carbon atoms) and a counter cation other than an iodonium cation; an adhesive agent or a sealing material which contains the resin composition; a cured product of the resin composition; a semiconductor device which comprises the cured product; and an electronic component.

Description

Resin compositions, adhesives, sealing materials, cured products, semiconductor devices and electronic components

[0001] The present invention relates to a resin composition, an adhesive or sealing material containing the same, a cured product thereof, and a semiconductor device and an electronic component containing the cured product.

[0002] Currently, adhesives, sealants, etc. containing curable resin compositions, particularly epoxy resin compositions, are often used in the assembly and mounting of semiconductor devices and electronic components, such as semiconductor chips, for the purpose of maintaining reliability, etc. While various devices, including smartphones, are being developed for IoT (Internet of Things) applications, the inability to manufacture them at high temperatures due to component issues, etc., has become an issue.

[0003] Development of adhesives that can be photocured and / or cured at low temperatures is underway. For example, Patent Document 1 discloses a UV / heat-curable adhesive composition that does not use an antimony compound as a thermal cationic polymerization initiator, is low in toxicity, can be cured at a low temperature of 120°C or less, and produces a cured product with excellent heat resistance. The composition contains an oxetane compound, an alicyclic epoxy compound, an aromatic glycidyl ether epoxy compound, a photo cationic polymerization initiator, and a thermal cationic polymerization initiator containing a tetrakis(pentafluorophenyl)borate compound in specific blending amounts.

[0004] Japanese Patent Application Laid-Open No. 2021-147584

[0005] Semiconductor devices and electronic components are exposed to high-temperature, high-humidity environments depending on their usage. Therefore, the cured product of an adhesive used in the manufacture of semiconductor devices and electronic components is required to have excellent reliability under high-temperature, high-humidity conditions. In particular, the glass transition temperature (Tg) of an adhesive used in semiconductor devices and electronic components is the temperature at which physical properties that affect the reliability of the semiconductor device or electronic component, such as the linear expansion coefficient, elastic modulus, and adhesive strength, change significantly. Therefore, even after the cured product of the adhesive is left in a high-temperature, high-humidity environment for a long period of time, it is required that the change in Tg between the initial Tg and the Tg after leaving the high-temperature, high-humidity environment is small.

[0006] It was found that the cured product of the adhesive composition disclosed in Patent Document 1 exhibited a large change in Tg before and after a pressure cooker test (PCT) to evaluate resistance to high temperatures and high humidity.

[0007] The present invention aims to provide a resin composition that can be cured at least by light or at a low temperature (for example, 100°C or less) and that gives a cured product that has excellent reliability under high temperature and high humidity conditions, an adhesive or sealant containing the same, a cured product thereof, and a semiconductor device and electronic component that contain the cured product.

[0008] Specific means for solving the above problems are as follows: The present invention encompasses a curable resin composition, an adhesive or sealant, a cured product, and a semiconductor device or electronic component, each having the following aspects: [1] (A) an alicyclic epoxy compound, (B) an oxetane compound, (C) a filler, and (D) a compound represented by the following formula (1): (In the formula, R １ , R ２ , R ３ and R ４ each independently represents an alkyl group having 1 to 18 carbon atoms or an aryl group having 6 to 14 carbon atoms, provided that R １ , R ２ , R ３ and R ４and a counter cation other than an iodonium cation. [2] The resin composition according to the above [1], wherein the (D) acid generator is a thermal acid generator (D1). [3] The resin composition according to the above [1], wherein the (D) acid generator is a photoacid generator (D2). [4] The resin composition according to the above [1], wherein the (D) acid generator is a combination of a thermal acid generator (D1) and a photoacid generator (D2). [5] The resin composition according to any one of the above [1] to [4], wherein the counter cation in the (D) acid generator is a sulfonium cation or an ammonium cation. [6] The resin composition according to any one of the above [1] to [5], wherein the content of the (D) acid generator is 0.1 to 10 parts by weight per 100 parts by weight of the total amount of the resin composition. [7] The resin composition according to any one of [1] to [6] above, further comprising (E) an acid generator other than component (D). [8] The resin composition according to [7] above, wherein the acid generator other than component (D) comprises a sulfonium cation or an ammonium cation. [9] The resin composition according to any one of [1] to [8] above, further comprising (F) an epoxy compound other than an alicyclic epoxy compound.

[10] The resin composition according to [9] above, wherein the epoxy compound other than (F) an alicyclic epoxy compound comprises an epoxy compound having an epoxy equivalent of 90 to 1,000 g / eq.

[11] The resin composition according to [9] or

[10] above, wherein the content of the epoxy compound other than (F) an alicyclic epoxy compound is 50 to 200 parts by weight per 100 parts by weight of the (A) alicyclic epoxy compound.

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

[11] above, wherein the content of all epoxy compounds contained in the resin composition is 100 to 1,300 parts by weight per 100 parts by weight of the (B) oxetane compound.

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

[12] above, wherein components (A) to (D) are contained in a single container.

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

[12] above, wherein components (A) to (D) are divided into two or more containers.

[15] An adhesive or sealant comprising the resin composition according to any one of [1] to

[14] above.

[16] A cured product obtained by curing the resin composition according to any one of [1] to

[14] above, or the adhesive or sealant according to

[15] above.

[17] A semiconductor device or electronic component comprising the cured product according to

[16] above.

[0009] According to aspects of the present invention, there are provided a resin composition that can be cured at least by light or at a low temperature (for example, 100°C or less) and that gives a cured product that has excellent reliability under high temperature and high humidity conditions, an adhesive or sealant containing the same, a cured product thereof, and a semiconductor device and an electronic component that contain the cured product.

[0010] In this specification, following the convention in the field of synthetic resins, a name including the term "resin," which normally refers to a polymer (particularly a synthetic polymer), may be used for a component constituting a curable resin composition before curing, even if the component is not a polymer, for example, a prepolymer compound before curing.

[0011] [Resin Composition] The resin composition according to one embodiment of the present invention comprises: (A) an alicyclic epoxy compound; (B) an oxetane compound; (C) a filler; and (D) a compound represented by the following formula (1): (In the formula, R １ , R ２ , R ３ and R ４ each independently represents an alkyl group having 1 to 18 carbon atoms or an aryl group having 6 to 14 carbon atoms, provided that R １ , R ２ , R ３ and R ４ and a counter cation other than an iodonium cation. According to this aspect, there is provided a resin composition that can be cured at least with light or at low temperatures (for example, 100°C or less) and that gives a cured product that has excellent reliability under high temperatures and high humidity conditions.

[0012] (A) Alicyclic Epoxy Compound The resin composition of this embodiment contains (A) an alicyclic epoxy compound (hereinafter also referred to as "component (A)"). One type of alicyclic epoxy compound is a compound having at least one alicyclic epoxy group in the molecule, i.e., a cycloalkene oxide structure. The cycloalkene oxide structure is a structure in which an alicyclic ring and an epoxy ring share a portion of the ring structure, such as a cyclohexene oxide structure or a cyclopentene oxide structure obtained by epoxidizing a cyclohexene ring-containing compound or a cyclopentene ring-containing compound with an oxidizing agent. From the viewpoint of ensuring heat resistance, the alicyclic epoxy compound preferably has 2 to 6 alicyclic epoxy groups, and even more preferably has 2 alicyclic epoxy groups. The number of carbon atoms in the alicyclic ring is not particularly limited. The alicyclic ring of the cycloalkene oxide structure is, for example, preferably a 5- to 8-membered ring, more preferably a 5- or 6-membered ring, and even more preferably a 6-membered ring. In this specification, the alicyclic epoxy compound may have an epoxy group other than an alicyclic epoxy group. Furthermore, a compound having an aromatic ring also falls under the category of an alicyclic epoxy compound if it has an alicyclic epoxy group.

[0013] Examples of the alicyclic epoxy compound include 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate (Celloxide (registered trademark) 2021P manufactured by Daicel Corporation, etc.), 3,4-epoxy-1-methylcyclohexyl-3,4-epoxy-1-methylhexanecarboxylate, 6-methyl-3,4-epoxycyclohexylmethyl-6-methyl-3,4-epoxycyclohexanecarboxylate, 3,4-epoxy-3-methylcyclohexylmethyl-3,4-epoxy-3-methylcyclohexanecarboxylate, 3,4-epoxy-5-methylcyclohexylmethyl-3,4-epoxy-5-methylcyclohexanecarboxylate, bis(3,4-epoxycyclohexylmethyl)adipate, 3,4-epoxy-6-methylcyclohexanecarboxylate, methylenebis(3,4-epoxycyclohexane), propane-2,2-diyl-bis(3,4-epoxycyclohexane), 2,2-bis(3, 4-epoxycyclohexyl)propane, dicyclopentadiene diepoxide, ethylene bis(3,4-epoxycyclohexanecarboxylate), limonene dioxide (1,2:8,9-diepoxylimonene), (3,3',4,4'-diepoxy)bicyclohexyl (Celloxide (registered trademark) 8010 manufactured by Daicel Corporation, etc.), dioctyl epoxyhexahydrophthalate, di-2-ethylhexyl epoxyhexahydrophthalate, 1-epoxyethyl-3,4-epoxy

[0033] Examples of epoxy cyclohexane include, but are not limited to, 2,2-bis(3,4-epoxycyclohexyl)propane, 1,2-bis(3,4-epoxycyclohexyl)ethane, 1,2-epoxy-1,2-bis(3,4-epoxycyclohexyl-1-yl)ethane, bis(3,4-epoxycyclohexylmethyl)ether, and the like.

[0014] In this specification, the term "alicyclic epoxy compound" includes not only compounds having the above-mentioned cycloalkene oxide structure, but also compounds containing an epoxy group other than an alicyclic epoxy group and an aliphatic ring, and compounds having an epoxy group in which oxygen atoms are bonded to two carbon atoms in an aliphatic chain. Examples of such alicyclic epoxy compounds include, but are not limited to, 1,2-epoxy-4-(2-oxiranyl)cyclohexane adduct of 2,2-bis(hydroxymethyl)-1-butanol (e.g., EHPE3150 manufactured by Daicel Corporation), epoxidized polybutadiene (e.g., EPOLEAD PB manufactured by Daicel Corporation), and compounds in which some or all of the double bonds of a styrene-butadiene copolymer have been epoxidized (e.g., EPOFRIEND manufactured by Daicel Corporation).

[0015] The epoxy equivalent of the alicyclic epoxy compound is preferably 90 to 1000 g / eq, more preferably 100 to 800 g / eq, further preferably 100 to 500 g / eq, and particularly preferably 110 to 300 g / eq.

[0016] The alicyclic epoxy compounds may be used alone or in combination of two or more.

[0017] In this embodiment, the content of the (A) alicyclic epoxy compound in the resin composition is preferably 1 to 70 wt %, more preferably 5 to 60 wt %, even more preferably 10 to 50 wt %, and particularly preferably 10 to 40 wt %, relative to the total weight of the resin composition. The content of the (A) alicyclic epoxy compound in the resin composition is preferably 10 to 1,000 parts by weight, more preferably 30 to 800 parts by weight, and even more preferably 40 to 600 parts by weight, relative to 100 parts by weight of the (B) oxetane compound described below.

[0018] (B) Oxetane Compound The resin composition of this embodiment contains (B) an oxetane compound (hereinafter also referred to as "component (B)"). The oxetane compound is a compound having at least one oxetane ring (e.g., a 3-oxetanyl group) in the molecule. Although the polymerization initiation reaction of an oxetane compound is slower than that of an alicyclic epoxy compound, it polymerizes rapidly once the polymerization initiation species reaches a certain concentration or higher, thereby contributing to the curing reaction of the resin composition at low temperatures in a short time. Furthermore, by including an oxetane compound in the resin composition, the change in Tg of the cured product is reduced even after the cured product is stored in a high-temperature, high-humidity environment for a long period of time. In one embodiment, the oxetane compound preferably has 1 to 6 oxetane rings in the molecule, and more preferably has 1 to 2 oxetane rings in the molecule.

[0019] Examples of oxetane compounds include, but are not limited to, bis[1-ethyl(3-oxetanyl)]methyl ether (also known as (3-ethyl-3{[(3-ethyloxetan-3-yl)methoxy]methyl}oxetane)), xylylene bisoxetane, 4,4'-bis[3-ethyl-(3-oxetanyl)methoxymethyl]biphenyl, 1,4-bis(3-ethyl-3-oxetanylmethoxy)methylbenzene, (bis[(3-ethyl-3-oxetanyl)methyl]isophthalate), 3-ethyl-3-hydroxymethyloxetane, 2-ethylhexyloxetane, (3-ethyloxetan-3-yl)methyl methacrylate, 3-ethyl-3-[(2-ethylhexyloxy)methyl]oxetane, 3-ethyl-3-(4-hydroxybutyl)oxymethyloxetane, 3-ethyl-3-phenoxymethyloxetane, and the like. Other examples of the oxetane compound include oxetanyl silsesquioxetane (such as OXT-191 manufactured by Toagosei Co., Ltd.), 3-ethyl-3{[(3-ethyloxetan-3-yl)methoxy]methyl}oxetane (such as OXT-221 manufactured by Toagosei Co., Ltd.), and phenol novolac oxetane (such as PHOX manufactured by Toagosei Co., Ltd.). Any one of the oxetane compounds may be used alone, or two or more of them may be used in combination.

[0020] The oxetane equivalent of the oxetane compound is preferably 90 to 500 g / eq, and may be 100 to 300 g / eq.

[0021] The content of the (B) oxetane compound in the resin composition is preferably 1 to 50 wt %, more preferably 2 to 40 wt %, and even more preferably 3 to 30 wt %, relative to the total weight of the resin composition. From the viewpoint of low-temperature curing properties, the content of the (B) oxetane compound in the resin composition is preferably 1 to 100 parts by weight, more preferably 5 to 85 parts by weight, relative to 100 parts by weight of the total content of all epoxy compounds contained in the resin composition. The total epoxy compounds refers to the sum of the (A) alicyclic epoxy compound and epoxy compounds other than the (F) alicyclic epoxy compound described below.

[0022] (C) Filler The resin composition of this embodiment contains (C) filler (hereinafter also referred to as "component (C)"). By containing a filler in the resin composition, the fluidity, injectability, coatability, adhesion, etc. of the resin composition can be improved. In particular, even when the resin composition is cured by heating at a low temperature of 100°C or less, a cured product with good adhesion to the adherend can be obtained. Fillers are broadly classified into inorganic fillers and organic fillers.

[0023] The inorganic filler is not particularly limited as long as it is made of granular material formed from an inorganic material and has the effect of lowering the linear expansion coefficient when added. Examples of inorganic materials that can be used include silica, talc, alumina, aluminum nitride, calcium carbonate, aluminum silicate, magnesium silicate, magnesium carbonate, barium sulfate, barium carbonate, lime sulfate, aluminum hydroxide, calcium silicate, potassium titanate, titanium oxide, zinc oxide, silicon carbide, silicon nitride, and boron nitride. One or more inorganic fillers may be used, or two or more may be used in combination. As the inorganic filler, silica filler is preferably used because it allows for a high loading. Amorphous silica is preferred as the silica. The surface of the inorganic filler may be surface-treated with a coupling agent such as a silane coupling agent.

[0024] Examples of the organic filler include polytetrafluoroethylene (PTFE) filler, silicone filler, acrylic filler, filler having a urethane skeleton, filler having a butadiene skeleton, styrene filler, etc. The organic filler may be surface-treated.

[0025] The shape of the filler is not particularly limited, and may be any of spherical, flaky, needle-like, irregular, etc.

[0026] The average particle size of the filler is preferably 6.0 μm or less, more preferably 5.0 μm or less, and even more preferably 4.0 μm or less. In this specification, unless otherwise specified, the average particle size refers to the volume-based median diameter (d ５０ ) By setting the average particle size of the filler to the upper limit or less, sedimentation of the filler can be suppressed, and the formation of coarse particles can be suppressed, which can prevent wear on the jet dispenser nozzle and scattering of the resin composition ejected from the jet dispenser nozzle outside the desired area. The lower limit of the average particle size of the filler is not particularly limited, but from the viewpoint of the viscosity of the resin composition, it is preferably 0.005 μm or more, and more preferably 0.01 μm or more. In some embodiments of this aspect, the average particle size of the filler is preferably 0.01 μm to 5.0 μm, and more preferably 0.1 μm to 3.0 μm. Fillers with different average particle sizes may be used in combination. For example, a filler having an average particle size of 0.005 μm or more but less than 0.1 μm may be used in combination with a filler having an average particle size of 0.1 μm to 6.0 μm.

[0027] The filler may be used alone or in combination of two or more.

[0028] The content of the filler in the resin composition of this embodiment is preferably 15 to 50 wt %, more preferably 20 to 45 wt %, and even more preferably 30 to 45 wt %, relative to the total weight of the resin composition.

[0029] (D) Acid Generator The resin composition of this embodiment contains (D) an acid generator represented by the following formula (1): (In the formula, R １ , R ２ , R ３ and R ４ each independently represents an alkyl group having 1 to 18 carbon atoms or an aryl group having 6 to 14 carbon atoms, provided that R １ , R ２ , R ３ and R ４ and a counter cation other than an iodonium cation. The resin composition includes an acid generator (hereinafter also referred to as "(D) acid generator," "(D) gallate acid generator," or "component (D)") that is a salt formed from an anion represented by formula (1) (hereinafter also referred to as "gallate anion") and a counter cation other than an iodonium cation. The acid generator generates an acid as an active species in response to light or heat, thereby promoting polymerization of the cationically polymerizable compound. By including an acid generator that is a salt formed from an anion represented by formula (1) (hereinafter also referred to as "gallate anion") and a counter cation other than an iodonium cation, the resin composition can be cured at least by light or at low temperatures (for example, 100°C or less) and can give a cured product that exhibits excellent reliability under high temperatures and high humidity conditions.

[0030] By including an acid generator having the above-described specific structure in a resin composition, the composition can be cured at least by light or at low temperatures (e.g., 100°C or less). Furthermore, the present inventors have found that, when a resin composition includes an acid generator having this specific structure, the change in Tg of the cured product is small even after the cured product is left in a high-temperature, high-humidity environment for a long period of time, specifically, after a pressure cooker test (PCT) under conditions of 2 atm, 121°C, 100% RH, and 20 hours. The reasons for this are thought to be, but are not limited to, the following: The cation moiety of the acid generator is decomposed by reaction, while the anion moiety remains in the cured product of the composition. When the cured product is left in a high-temperature, high-humidity environment for a long period of time, an acid is generated by moisture that penetrates into the cured product. The generated acid migrates through moisture, which is a polar solvent, and can cleave crosslinks in the cured product. The gallate anion in the acid generator of this embodiment has a large ionic radius and molecular weight, so it is believed that it cannot migrate in the cured product, making it less likely to undergo a reaction that cleaves crosslinks. Furthermore, since the counter cation in the acid generator of this embodiment is other than an iodonium cation, when a cured product of the composition is placed in a high-temperature, high-humidity environment for a long period of time, iodic acid resulting from the iodonium cation is not generated, and a crosslink cleavage reaction due to iodic acid does not occur.

[0031] In one embodiment, the (D) acid generator is a (D1) thermal acid generator. In one embodiment, the (D) acid generator is a (D2) photoacid generator. In one embodiment, the (D) acid generator is a combination of a (D1) thermal acid generator and a (D2) photoacid generator.

[0032] In formula (1), R １ , R ２ , R ３ and R ４ each independently represents an alkyl group having 1 to 18 carbon atoms or an aryl group having 6 to 14 carbon atoms, and R １ , R ２ , R ３ and R ４ At least one of R represents an aryl group having 6 to 14 carbon atoms. １ , R ２ , R ３ and R ４is any combination of the following: (i) R １ , R ２ , R ３ and R ４ (ii) R is a combination of one aryl group and the remaining three alkyl groups. １ , R ２ , R ３ and R ４ (iii) R is a combination of two aryl groups and the remaining two alkyl groups. １ , R ２ , R ３ and R ４ (iv) R is a combination of three aryl groups and the remaining one alkyl group. １ , R ２ , R ３ and R ４ Among the above combinations, the anion of (iii) or (iv) is preferred, and the anion of (iv) is more preferred.

[0033] R in formula (1) １ , R ２ , R ３ and R ４ The alkyl group having 1 to 18 carbon atoms represented by may be any of a linear, branched, or cyclic alkyl group, and specific examples thereof include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a t-butyl group, an n-pentyl group, an isopentyl group, a t-pentyl group, a sec-pentyl group, an n-hexyl group, an isohexyl group, an n-heptyl group, a sec-heptyl group, an n-octyl group, an n-nonyl group, a sec-nonyl group, an n-decyl group, an n-undecyl group, an n-dodecyl group, an n-tridecyl group, an n-tetradecyl group, an n-pentadecyl group, an n-hexadecyl group, an n-heptadecyl group, an n-octadecyl group, a cyclopentyl group, and a cyclohexyl group. １ , R ２ , R ３ and R ４The alkyl group having 1 to 18 carbon atoms represented by may have a substituent. The term "substituted alkyl group" used herein means an alkyl group in which a hydrogen atom in the alkyl group structure is substituted with a substituent, and the position and number of the substituent are not particularly limited. When the substituent has a carbon atom, R １ , R ２ , R ３ and R ４ The number of carbon atoms in the alkyl group represented by does not include the number of carbon atoms in the substituent. Specifically, for example, an ethyl group having a phenyl group as a substituent is an alkyl group having two carbon atoms.

[0034] R in formula (1) １ , R ２ , R ３ and R ４ The substituents that the alkyl group having 1 to 18 carbon atoms represented by the formula (I) may have are not particularly limited (excluding alkyl groups). Examples of such substituents include an alkoxy group, an aromatic group, a heterocyclic group, a halogen atom, a hydroxyl group, a mercapto group, a nitro group, an alkyl-substituted amino group, an aryl-substituted amino group, an unsubstituted amino group (NH ２ group), a cyano group, an isocyano group, etc.

[0035] R in formula (1) １ , R ２ , R ３ and R ４ The alkoxy group that may be substituted on the alkyl group having 1 to 18 carbon atoms represented by is a substituent in which an oxygen atom and an alkyl group are bonded. Examples of the alkyl group that this alkoxy group has include, for example, R １ , R ２ , R ３ and R ４ The alkyl groups represented by R in formula (1) are the same as those described in the section on the alkyl group having 1 to 18 carbon atoms. １ , R ２ , R ３ and R ４The aromatic group that may be substituted on the alkyl group having 1 to 18 carbon atoms represented by is not particularly limited as long as it is a residue in which one hydrogen atom has been removed from the aromatic ring of an aromatic compound. Examples of such aromatic groups include a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, a tolyl group, an indenyl group, a naphthyl group, an anthryl group, a fluorenyl group, a pyrenyl group, a phenanthenyl group, and a mestyl group. １ , R ２ , R ３ and R ４ The heterocyclic group which may be substituted by the alkyl group having 1 to 18 carbon atoms represented by the formula (I) is not particularly limited as long as it is a residue in which one hydrogen atom has been removed from the heterocyclic ring of a heterocyclic compound. Examples of such heterocyclic groups include a furanyl group, a thienyl group, a thienothienyl group, a pyrrolyl group, an imidazolyl group, an N-methylimidazolyl group, a thiazolyl group, an oxazolyl group, a pyridyl group, a pyrazyl group, a pyrimidyl group, a quinolyl group, an indolyl group, a benzopyrazyl group, a benzopyrimidyl group, a benzothienyl group, a naphthothienyl group, a benzofuranyl group, a benzothiazolyl group, a pyridinothiazolyl group, a benzimidazolyl group, a pyridinoimidazolyl group, an N-methylbenzimidazolyl group, a pyridino-N-methylimidazolyl group, a benzoxazolyl group, a pyridinooxazolyl group, a benzothiadiazolyl group, a pyridinothiadiazolyl group, a benzoxadiazolyl group, a pyridinooxadiazolyl group, a carbazolyl group, a phenoxazinyl group, and a phenothiazinyl group. １ , R ２ , R ３ and R ４ Examples of the halogen atom that may be substituted on the alkyl group having 1 to 18 carbon atoms represented by the formula (1) include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. １ , R ２ , R ３ and R ４ The alkyl-substituted amino group that may be substituted by the alkyl group having 1 to 18 carbon atoms represented by may be either a mono-alkyl-substituted amino group or a di-alkyl-substituted amino group. Examples of the alkyl group in these alkyl-substituted amino groups include R１ , R ２ , R ３ and R ４ The alkyl groups represented by R in formula (1) are the same as those described in the section on the alkyl group having 1 to 18 carbon atoms. １ , R ２ , R ３ and R ４ The aryl-substituted amino group which may be substituted by the alkyl group having 1 to 18 carbon atoms represented by the formula (1) may be either a monoaryl-substituted amino group or a diaryl-substituted amino group. The aryl group in these aryl-substituted amino groups is R １ , R ２ , R ３ and R ４ Examples of the aromatic groups include the same aromatic groups that may be substituted on the alkyl group having 1 to 18 carbon atoms represented by the formula (I).

[0036] R in formula (1) １ , R ２ , R ３ and R ４ Specific examples of the aryl group having 6 to 14 carbon atoms represented by R in formula (1) include １ , R ２ , R ３ and R ４ Examples of the aromatic groups include the same as the aromatic groups which may be substituted on the alkyl group having 1 to 18 carbon atoms represented by the formula (I).

[0037] R in formula (1) １ , R ２ , R ３ and R ４ The aryl group having 6 to 14 carbon atoms represented by may have a substituent. The term "substituted aryl group" used herein means an aryl group in which a hydrogen atom in the structure of the aryl group is substituted with a substituent, and the position and number of the substituent are not particularly limited. When the substituent has a carbon atom, R １ , R ２ , R ３ and R ４ The number of carbon atoms in the aryl group represented by does not include the number of carbon atoms in the substituent. Specifically, for example, a phenyl group having an ethyl group as a substituent is an aryl group having 6 carbon atoms.

[0038] R in formula (1) １ , R ２ , R ３ and R ４ There is no particular limitation on the substituent that the aryl group having 6 to 14 carbon atoms represented by the formula (I) may have. Examples of such a substituent include an alkyl group, an alkoxy group, an aromatic group, a heterocyclic group, a halogen atom, a hydroxyl group, a mercapto group, a nitro group, an alkyl-substituted amino group, an aryl-substituted amino group, an unsubstituted amino group (NH ２ group), a cyano group, an isocyano group, etc.

[0039] R in formula (1) １ , R ２ , R ３ and R ４ Examples of the alkyl group that may be substituted on the aryl group having 6 to 14 carbon atoms represented by R １ , R ２ , R ３ and R ４ The alkyl groups represented by R in formula (1) are the same as those described in the section on the alkyl group having 1 to 18 carbon atoms. １ , R ２ , R ３ and R ４ Specific examples of the alkoxy group, aromatic group, heterocyclic group, halogen atom, alkyl-substituted amino group and aryl-substituted amino group that may be substituted by the aryl group having 6 to 14 carbon atoms represented by R in formula (1) include: １ , R ２ , R ３ and R ４ Examples of the alkoxy group, aromatic group, heterocyclic group, halogen atom, alkyl-substituted amino group and aryl-substituted amino group that may be substituted by the alkyl group having 1 to 18 carbon atoms represented by the formula (I) include the same as the alkoxy group, aromatic group, heterocyclic group, halogen atom, alkyl-substituted amino group and aryl-substituted amino group that may be substituted by the alkyl group having 1 to 18 carbon atoms represented by the formula (I).

[0040] R in formula (1) １ , R ２ , R ３ and R ４ As the alkyl group, a phenyl group having a perfluoroalkyl group as a substituent or a phenyl group having a fluorine atom as a substituent is preferred, and a pentafluorophenyl group or a bis(trifluoromethyl)phenyl group is more preferred.

[0041] Specific examples of the gallate anion of formula (1) include, but are not limited to, the following:

[0042] The counter cation other than the iodonium cation that forms a salt with the gallate anion represented by (1) is not particularly limited as long as it is a monovalent cation other than the iodonium cation, and examples thereof include a sulfonium cation, an ammonium cation, and a phosphonium cation. In one embodiment, the counter cation is preferably a sulfonium cation or an ammonium cation, and more preferably a sulfonium cation.

[0043] When the acid generator (D) is a thermal acid generator (D1), the counter cation other than the iodonium cation that forms a salt with the gallate anion represented by formula (1) is, from the viewpoint of efficiently generating an acid by heat, a cation represented by the following formula (2): (In the formula, R ５ and R ６ is an alkyl group or an aralkyl group, R ７ represents hydrogen, an alkyl group, a hydroxy group, a carboxy group, an alkoxy group, an aryloxy group, an alkylcarbonyl group, an arylcarbonyl group, an aralkylcarbonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an aralkyloxycarbonyl group, an alkylcarbonyloxy group, an arylcarbonyloxy group, an aralkylcarbonyloxy group, an alkoxycarbonyloxy group, an aryloxycarbonyloxy group, an aralkyloxycarbonyloxy group, an arylthiocarbonyl group, an acyloxy group, an arylthio group, an alkylthio group, an aryl group, a heterocyclic hydrocarbon group, an alkylsulfinyl group, an arylsulfinyl group, an alkylsulfonyl group, an arylsulfonyl group, a hydroxy(poly)alkyleneoxy group, an optionally substituted silyl group and an amino group, a cyano group, a nitro group, or a halogen atom; ７ n represents an integer of 0 to 5, and when n is 2 to 5, R ７ may be the same or different, and two or more R ７ are directly connected to each other or -O-, -S-, -SO-, -SO２ A sulfonium cation represented by the following formula (1) may form a ring structure containing the element S via -, -NH-, -CO-, -COO-, -CONH-, an alkylene group or a phenylene group.

[0044] In formula (2), R ５ , R ６ and R ７ The alkyl group represented by is R １ , R ２ , R ３ and R ４ Examples of the alkyl group include the same alkyl groups as those described in the section on the alkyl group having 1 to 18 carbon atoms represented by the formula (I).

[0045] In formula (2), R ５ and R ６ Examples of the aralkyl group represented by the formula (I) include a lower alkyl group substituted with an aryl group having 6 to 10 carbon atoms. Specific examples of the aralkyl group include a benzyl group, a 2-methylbenzyl group, a 1-naphthylmethyl group, and a 2-naphthylmethyl group.

[0046] In formula (2), R ７ Examples of the alkoxy group represented by include a straight-chain alkoxy group having 1 to 18 carbon atoms, and a branched-chain alkoxy group having 3 to 18 carbon atoms. Specific examples of the alkoxy group include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, hexyloxy, decyloxy, dodecyloxy, and octadecyloxy.

[0047] In formula (2), R ７ The aryloxy group represented by the formula (I) includes an aryloxy group having 6 to 10 carbon atoms, and specific examples thereof include phenoxy and naphthyloxy.

[0048] In formula (2), R ７Examples of the alkylcarbonyl group represented by the formula (I) include a linear alkylcarbonyl group having 2 to 18 carbon atoms and a branched alkylcarbonyl group having 4 to 18 carbon atoms. Specific examples of the alkylcarbonyl group include acetyl, propionyl, butanoyl, 2-methylpropionyl, heptanoyl, 2-methylbutanoyl, 3-methylbutanoyl, octanoyl, decanoyl, dodecanoyl, and octadecanoyl.

[0049] In formula (2), R ７ The arylcarbonyl group represented by the formula (I) includes an arylcarbonyl group having 7 to 11 carbon atoms, and specific examples thereof include benzoyl and naphthoyl.

[0050] In formula (2), R ７ The aralkylcarbonyl group represented by the formula (I) includes a lower alkylcarbonyl group substituted with an aryl group having 6 to 10 carbon atoms, and specific examples thereof include benzylcarbonyl, 2-methylbenzylcarbonyl, 1-naphthylmethylcarbonyl, 2-naphthylmethylcarbonyl, etc.

[0051] In formula (2), R ７ Examples of the alkoxycarbonyl group represented by the formula (I) include a straight-chain alkoxycarbonyl group having 2 to 19 carbon atoms and a branched-chain alkoxycarbonyl group having 4 to 19 carbon atoms. Specific examples of the alkoxycarbonyl group include methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl, tert-butoxycarbonyl, octyloxycarbonyl, tetradecyloxycarbonyl, and octadecyloxycarbonyl.

[0052] In formula (2), R ７ The aryloxycarbonyl group represented by the formula (I) includes an aryloxycarbonyl group having 7 to 11 carbon atoms, and specific examples thereof include phenoxycarbonyl and naphthoxycarbonyl.

[0053] In formula (2), R ７The aralkyloxycarbonyl group represented by the formula (I) includes a lower alkoxycarbonyl group substituted with an aryl group having 6 to 10 carbon atoms, such as benzyloxycarbonyl, 2-methylbenzyloxycarbonyl, 1-naphthylmethyloxycarbonyl, and 2-naphthylmethyloxycarbonyl.

[0054] In formula (2), R ７ The alkylcarbonyloxy group represented by the formula (I) includes a straight-chain or branched-chain alkylcarbonyloxy group having 2 to 19 carbon atoms, and specific examples thereof include acetoxy, ethylcarbonyloxy, propylcarbonyloxy, isopropylcarbonyloxy, butylcarbonyloxy, isobutylcarbonyloxy, sec-butylcarbonyloxy, tert-butylcarbonyloxy, octylcarbonyloxy, tetradecylcarbonyloxy, and octadecylcarbonyloxy.

[0055] In formula (2), R ７ The arylcarbonyloxy group represented by the formula (I) includes an arylcarbonyloxy group having 7 to 11 carbon atoms. Specific examples thereof include benzoyloxy and naphthoyloxy.

[0056] In formula (2), R ７ The aralkylcarbonyloxy group represented by the formula (I) includes a lower alkylcarbonyl group substituted with an aryl group having 6 to 10 carbon atoms, and specific examples thereof include benzylcarbonyloxy, 2-methylbenzylcarbonyloxy, 1-naphthylmethylcarbonyloxy, 2-naphthylmethylcarbonyloxy, etc.

[0057] In formula (2), R ７The alkoxycarbonyloxy group represented by the formula (I) includes a straight-chain or branched-chain alkoxycarbonyl group having 2 to 18 carbon atoms or 2 to 19 carbon atoms. Specific examples thereof include methoxycarbonyloxy, ethoxycarbonyloxy, propoxycarbonyloxy, isopropoxycarbonyloxy, butoxycarbonyloxy, isobutoxycarbonyloxy, sec-butoxycarbonyloxy, tert-butoxycarbonyloxy, octyloxycarbonyloxy, tetradecyloxycarbonyloxy, and octadecyloxycarbonyloxy.

[0058] In formula (2), R ７ The aryloxycarbonyloxy group represented by the formula (I) includes an aryloxycarbonyloxy group having 7 to 11 carbon atoms. Specific examples thereof include phenoxycarbonyloxy and naphthoxycarbonyloxy.

[0059] In formula (2), R ７ The aralkyloxycarbonyloxy group represented by the formula (I) includes a lower alkoxycarbonyloxy group substituted with an aryl group having 6 to 10 carbon atoms, specific examples of which include benzyloxycarbonyloxy, 2-methylbenzyloxycarbonyloxy, 1-naphthylmethyloxycarbonyloxy, 2-naphthylmethyloxycarbonyloxy, etc.

[0060] In formula (2), R ７ The arylthiocarbonyl group represented by the formula (I) includes an arylthiocarbonyl group having 7 to 11 carbon atoms, and specific examples thereof include phenylthiocarbonyl and naphthoxythiocarbonyl.

[0061] In formula (2), R ７Examples of the acyloxy group represented by the formula (I) include a linear acyloxy group having 2 to 19 carbon atoms and a branched acyloxy group having 4 to 19 carbon atoms. Specific examples of the acyloxy group include acetoxy, ethylcarbonyloxy, propylcarbonyloxy, isopropylcarbonyloxy, butylcarbonyloxy, isobutylcarbonyloxy, sec-butylcarbonyloxy, tert-butylcarbonyloxy, octylcarbonyloxy, tetradecylcarbonyloxy, and octadecylcarbonyloxy.

[0062] In formula (2), R ７ Examples of the arylthio group represented by the formula (I) include arylthio groups having 6 to 20 carbon atoms. Specific examples of the arylthio group include phenylthio, 2-methylphenylthio, 3-methylphenylthio, 4-methylphenylthio, 2-chlorophenylthio, 3-chlorophenylthio, 4-chlorophenylthio, 2-bromophenylthio, 3-bromophenylthio, 4-bromophenylthio, 2-fluorophenylthio, 3-fluorophenylthio, 4-fluorophenylthio, 2-hydroxyphenylthio, 4-hydroxyphenylthio, 2-methoxyphenylthio, 4-methoxyphenylthio, 1-naphthylthio, 2-naphthylthio, 4-[4-(phenylthio)benzoyl]phenylthio, and 4-[4-(phenylthio)phenoxy]phenylthio. nylthio, 4-[4-(phenylthio)phenyl]phenylthio, 4-(phenylthio)phenylthio, 4-benzoylphenylthio, 4-benzoyl-2-chlorophenylthio, 4-benzoyl-3-chlorophenylthio, 4-benzoyl-3-methylthiophenylthio, 4-benzoyl-2-methylthiophenylthio, 4-(4-methylthiobenzoyl)phenylthio, 4-(2-methylthiobenzoyl)phenylthio, 4-(p-methylbenzoyl)phenylthio, 4-(p-ethylbenzoyl)phenylthio, 4-(p-isopropylbenzoyl)phenylthio, and 4-(p-tert-butylbenzoyl)phenylthio.

[0063] In formula (2), R ７Examples of the alkylthio group represented by the formula (I) include a linear alkylthio group having 1 to 18 carbon atoms and a branched alkylthio group having 3 to 18 carbon atoms. Specific examples of the alkylthio group include methylthio, ethylthio, propylthio, isopropylthio, butylthio, isobutylthio, sec-butylthio, tert-butylthio, pentylthio, isopentylthio, neopentylthio, tert-pentylthio, octylthio, decylthio, dodecylthio, and isooctadecylthio.

[0064] In formula (2), R ７ The aryl group represented by the formula (I) includes aryl groups having 6 to 10 carbon atoms, and specific examples thereof include phenyl, tolyl, dimethylphenyl, and naphthyl.

[0065] In formula (2), R ７ Examples of the heterocyclic hydrocarbon group represented by the formula (I) include heterocyclic hydrocarbon groups having 4 to 20 carbon atoms. Specific examples thereof include thienyl, furanyl, pyranyl, pyrrolyl, oxazolyl, thiazolyl, pyridyl, pyrimidyl, pyrazinyl, indolyl, benzofuranyl, benzothienyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl, acridinyl, phenothiazinyl, phenazinyl, xanthenyl, thianthrenyl, phenoxazinyl, phenoxathiinyl, chromanyl, isochromanyl, dibenzothienyl, xanthonyl, thioxanthonyl, and dibenzofuranyl.

[0066] In formula (2), R ７ Examples of the alkylsulfinyl group represented by the formula (I) include a straight-chain alkylsulfinyl group having 1 to 18 carbon atoms and a branched-chain sulfinyl group having 3 to 18 carbon atoms. Specific examples thereof include methylsulfinyl, ethylsulfinyl, propylsulfinyl, isopropylsulfinyl, butylsulfinyl, isobutylsulfinyl, sec-butylsulfinyl, tert-butylsulfinyl, pentylsulfinyl, isopentylsulfinyl, neopentylsulfinyl, tert-pentylsulfinyl, octylsulfinyl, and isooctadecylsulfinyl.

[0067] In formula (2), R７ The arylsulfinyl group represented by the formula (I) includes an arylsulfinyl group having 6 to 10 carbon atoms, and specific examples thereof include phenylsulfinyl, tolylsulfinyl, and naphthylsulfinyl.

[0068] In formula (2), R ７ Examples of the alkylsulfonyl group represented by the formula (I) include linear alkylsulfonyl groups having 1 to 18 carbon atoms and branched alkylsulfonyl groups having 3 to 18 carbon atoms. Specific examples thereof include methylsulfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, butylsulfonyl, isobutylsulfonyl, sec-butylsulfonyl, tert-butylsulfonyl, pentylsulfonyl, isopentylsulfonyl, neopentylsulfonyl, tert-pentylsulfonyl, octylsulfonyl, and octadecylsulfonyl.

[0069] In formula (2), R ７ The arylsulfonyl group represented by the formula (I) includes arylsulfonyl groups having 6 to 10 carbon atoms. Specific examples thereof include phenylsulfonyl, tolylsulfonyl (tosyl group), naphthylsulfonyl, and the like.

[0070] In formula (2), R ７ Examples of the hydroxy(poly)alkyleneoxy group represented by formula (3) include a hydroxy(poly)alkyleneoxy group represented by formula (3): HO(—AO)q- (3) (wherein AO represents an ethyleneoxy group and / or a propyleneoxy group, and q represents an integer of 1 to 5).

[0071] In formula (2), R ７ The optionally substituted silyl group represented by the formula (I) includes a substituted silyl group having 1 to 18 carbon atoms. Specific examples thereof include silyl, methylsilyl, dimethylsilyl, trimethylsilyl, phenylsilyl, methylphenylsilyl, dimethylphenylsilyl, diphenylsilyl, diphenylmethylsilyl, triphenylsilyl, etc.

[0072] In formula (2), R ７ The amino group represented by is an amino group (-NH ２) and substituted amino groups having 1 to 15 carbon atoms. Specific examples of the substituted amino group include methylamino, dimethylamino, ethylamino, methylethylamino, diethylamino, n-propylamino, methyl-n-propylamino, ethyl-n-propylamino, n-propylamino, isopropylamino, isopropylmethylamino, isopropylethylamino, diisopropylamino, phenylamino, diphenylamino, methylphenylamino, ethylphenylamino, n-propylphenylamino, and isopropylphenylamino.

[0073] In formula (2), R ７ Examples of the halogen atom represented by include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

[0074] In formula (2), when n is 2 to 5, R ７ are mutually independent and may be the same or different.

[0075] R ７ is preferably a hydroxy group, an alkoxy group, an alkylcarbonyloxy group, or an aralkyloxycarbonyloxy group, and more preferably a hydroxy group, a methoxy group, an acetyloxy group, or a benzyloxycarbonyloxy group.

[0076] n is R ７ represents the number of ７ is an integer of 0 to 5, preferably 0 to 3, more preferably 0 to 2, and even more preferably 0 or 1. ７ When is in these preferred ranges, the thermal sensitivity of the sulfonium salt is further improved.

[0077] Among the groups represented by formula (2), preferred specific examples are shown below. More preferred are: ５ is a methyl group, and R ６ is a naphthyl group, and R ７ a sulfonium cation in which R is a hydroxy group; ５ is a methyl group, and R ６ is a benzyl group, and R ７a sulfonium cation in which R is a hydroxy group; ５ is a methyl group, and R ６ is a 4-nitrobenzyl group, and R ７ is a hydroxy group; and ５ and R ６ is a methyl group, and R ７ is a sulfonium cation in which the acetoxy group is

[0078] When the acid generator (D) is a photoacid generator (D2), the counter cation other than the iodonium cation that forms a salt with the gallate anion represented by formula (1) may be, from the viewpoint of efficiently generating an acid by light, for example, triphenylsulfonium, tri-p-tolylsulfonium, tri-o-tolylsulfonium, tris(4-methoxyphenyl)sulfonium, 1-naphthyldiphenylsulfonium, 2-naphthyldiphenylsulfonium, tris(4-fluorophenyl)sulfonium, tri-1-naphthylsulfonium, tri-2-naphthylsulfonium, phenylthio)phenylbis(4-fluorophenyl)sulfonium, 4-(phenylthio)phenylbis(4-methoxyphenyl)sulfonium, 4-(phenylthio)phenylbis(4-methoxyphenyl)sulfonium, 4-(phenylthio)phenyldi-p-tolylsulfonium, [4-(4-biphenylylthio)phenyl [4-(2-thioxanthonylthio)phenyl]diphenylsulfonium, bis[4-(diphenylsulfonio)phenyl]sulfide, bis[4-{bis[4-(2-hydroxyethoxy)phenyl]sulfonio}phenyl]sulfide, bis{4-[bis(4-fluorophenyl)sulfonio]phenyl}sulfide, bis{4-[bis(4-methylphenyl)sulfonio]phenyl}sulfide, bis{4-[bis(4-methoxyphenyl)sulfonio]phenyl}sulfide, 4-(4-benzoyl-2-chlorophenylthio)phenylbis(4-fluorophenyl)sulfonium, 4-(4-benzoyl-2-chlorophenylthio)phenyldiphenylsulfonium, 4-(4-benzoylphenylthio)phenylbis(4-fluorophenyl)sulfonium, 4-(4-benzoylphenylthio)phenyldiphenylsulfonium, 7-isopropyl-9-oxo-10-thia-9,10-dihydroanthracen-2-yldi-p-tolylsulfonium, 7-isopropyl-9-oxo-10-thia-9,10-dihydroanthracen-2-yldi-p-tolylsulfonium,10-Dihydroanthracen-2-yldiphenylsulfonium, 2-[(di-p-tolyl)sulfonio]thioxanthone, 2-[(diphenyl)sulfonio]thioxanthone, 4-(9-oxo-9H-thioxanthen-2-yl)thiophenyl-9-oxo-9H-thioxanthen-2-ylphenylsulfonium, 4-[4-(4-t-butylbenzoyl)phenylthio]phenyldi-p-tolylsulfonium, 4-[4-(4-t-butylbenzoyl)phenylthio]phenyldiphenylsulfonium, 4-[4-(benzoylphenylthio)]phenyldi-p-tolylsulfonium, 4-[4-(benzoylphenylthio)]phenyldiphenylsulfonium, 5-(4- triarylsulfoniums such as 5-(methoxyphenyl)thiaanthrenenium, 5-phenylthiaanthrenenium, 5-trilylthiaanthrenenium, 5-(4-ethoxyphenyl)thiaanthrenenium, and 5-(2,4,6-trimethylphenyl)thiaanthrenenium.

[0079] Examples of ammonium cations include pyrrolidiniums such as N,N-dimethylpyrrolidinium, N-ethyl-N-methylpyrrolidinium, and N,N-diethylpyrrolidinium; imidazoliniums such as N,N'-dimethylimidazolinium, N,N'-diethylimidazolinium, N-ethyl-N'-methylimidazolinium, 1,3,4-trimethylimidazolinium, and 1,2,3,4-tetramethylimidazolinium; tetrahydropyrimidiniums such as N,N'-dimethyltetrahydropyrimidinium; and morpholiniums such as N,N'-dimethylmorpholinium. pyridinium such as N-methylpyridinium, N-benzylpyridinium, and N-phenacylpyridinium; imidazolium such as N,N'-dimethylimidazolium; quinolium such as N-methylquinolium, N-benzylquinolium, and N-phenacylquinolium; isoquinolium such as N-methylisoquinolium; thiazonium such as benzylbenzothiazonium and phenacylbenzothiazonium; and acridium such as benzylacridium and phenacylacridium.

[0080] In this embodiment, the content of the acid generator (D) in the resin composition is preferably 0.1 to 10 parts by weight, more preferably 0.3 to 8 parts by weight, and even more preferably 0.5 to 5 parts by weight, per 100 parts by weight of the total amount of the resin composition. The content of the acid generator (D) in the resin composition is preferably 0.1 to 30 parts by weight, more preferably 0.5 to 20 parts by weight, and even more preferably 1 to 15 parts by weight, per 100 parts by weight of the total amount of the components (A) and (B). Furthermore, the content of the acid generator (D) in the resin composition is preferably 0.1 to 20 parts by weight, more preferably 0.5 to 15 parts by weight, and even more preferably 1 to 10 parts by weight, per 100 parts by weight of the total amount of the components (A), (B), and (F), which will be described later.

[0081] (E) Acid Generator Other Than Component (D) The resin composition of this embodiment may contain, if desired, an acid generator other than component (D) (E) (hereinafter also referred to as "component (E)"), as long as the effects of the present invention are not impaired. Surprisingly, as long as the resin composition of this embodiment contains the acid generator of component (D), even if it contains an acid generator other than component (D), the change in Tg of the cured product of the resin composition after being placed in a high-temperature, high-humidity environment for a long period of time was kept small. Examples of acid generators other than component (D) of (E) include BF ４ － , SbF ６ -, AsF ６ － , B(C ６ F ５ ) ４ － , C(CF ３ SO ２ ) ３ － , [P(R ８ ) ａ F ６－ａ ] － , [C(R ８ SO ２ ) ３ ] － , or [N(R ８ SO ２ ) ２ ] － (In the formula, R ８are each independently an alkyl group in which at least a portion of the hydrogen atoms is substituted with a fluorine atom, a is an integer of 0 to 5, and when a is an integer of 2 or more, a plurality of R ８ may be the same or different.) as a counter anion, and a sulfonium cation, an ammonium cation, a phosphonium cation, an iodonium cation, or the like as a cation moiety.

[0082] From the viewpoint of not impairing the effect of the excellent high-temperature, high-humidity reliability obtained by the acid generator (D), the acid generator (E) other than the component (D) preferably contains a sulfonium cation or an ammonium cation as the cation moiety, and more preferably contains a sulfonium cation. The acid generator (E) other than the component (D) may contain an iodonium cation within a range that does not impair the effects of the present invention, but preferably does not contain an iodonium cation.

[0083] In one embodiment, when the acid generator (D) is a thermal acid generator (D1), the acid generator (E) other than the component (D) is a photoacid generator. In one embodiment, when the acid generator (D) is a photoacid generator (D2), the acid generator (E) other than the component (D) is a thermal acid generator.

[0084] (E) As the acid generator other than the component (D), commercially available products can be used. Examples of commercially available products include photoacid generators that are borate-based sulfonium salts (product names: CPI-110B, CPI-310B, CPI-410B, etc., manufactured by San-Apro Co., Ltd.), PF ３ (C ２ F ５ ) ３ Photoacid generators which are sulfonium salts of PF (product names: CPI-210S, VC-1S, CPI-410S, etc., manufactured by San-Apro Co., Ltd.), ３ (C ２ F ５ ) ３Examples of suitable acid generators include, but are not limited to, thermal acid generators which are sulfonium salts of methyl methyl acrylate (product name: TA-100 manufactured by San-Apro Co., Ltd.), and thermal acid generators which are borate-based quaternary ammonium salts (product name: CXC-1821 manufactured by King Industries, Inc.). The acid generators other than component (D) (E) may be used alone or in combination of two or more.

[0085] The content of the acid generator (E) other than component (D) in the resin composition is preferably 0.5 to 10 parts by weight, and more preferably 0.5 to 5 parts by weight, per 100 parts by weight of the total of component (A), component (B), and component (F) described below.

[0086] (F) Epoxy Compounds Other Than Alicyclic Epoxy Compounds The resin composition of this embodiment may contain (F) an epoxy compound other than an alicyclic epoxy compound (hereinafter also referred to as "(F) other epoxy compound" or "component (F)"). Examples of epoxy compounds other than alicyclic epoxy compounds include monofunctional epoxy compounds having one epoxy group that is not an alicyclic epoxy group, and polyfunctional epoxy compounds having two or more epoxy groups that are not alicyclic epoxy groups. (F) Other epoxy compounds are broadly classified into epoxy compounds having an aromatic ring skeleton and aliphatic epoxy compounds.

[0087] Examples of epoxy compounds having an aromatic ring skeleton include polyfunctional epoxy resins, such as bisphenol A epoxy resins (for example, EPICLON (registered trademark) 850, 850-S, EXA-850CRP, EXA-8067, etc., manufactured by DIC Corporation), polyalkylene oxide-modified bisphenol A epoxy resins, for example, polypropylene oxide-modified bisphenol A epoxy resins (for example, AER9000 manufactured by Asahi Kasei Corporation, EP-4000S, EP-4003S, EP-4005, EP-4010S, manufactured by ADEKA Corporation), polyethylene oxide-modified bisphenol A epoxy resins (for example, Rikaresin BEO-60E manufactured by New Japan Chemical Co., Ltd.), bisphenol F epoxy resins (for example, EPICLON (registered trademark) 830-S, EXA-830LVP, etc., manufactured by DIC Corporation), bisphenol AD ​​epoxy resins, Examples of epoxy resins include, but are not limited to, bisphenol S type epoxy resins, naphthalene type epoxy resins (for example, EPICLON (registered trademark), HP-4032D, HP-720H, etc., manufactured by DIC Corporation), phenol novolac type epoxy resins (for example, EPICLON (registered trademark), N-740, N-770, etc., manufactured by DIC Corporation), cresol novolac type epoxy resins (for example, EPICLON (registered trademark), N-660, N-670, N-655-EXP-S, etc., manufactured by DIC Corporation), polyfunctional epoxy compounds such as glycidyl ethers of tetra(hydrophenyl)alkanes and glycidyl ethers of tetrahydroxybenzophenone, and epoxidized polyvinylphenols. Examples of monofunctional epoxy compounds having an aromatic ring skeleton include, but are not limited to, p-tert-butylphenyl glycidyl ether (e.g., ADEKA GLYCIROL (registered trademark), ED-509E, ED-509S, etc., manufactured by ADEKA Corporation) and 2-phenylphenol glycidyl ether (e.g., OPP-G, etc., manufactured by SANKO CO., LTD.).

[0088] Aliphatic epoxy compounds are epoxy compounds that do not have either an aromatic ring skeleton or an alicyclic epoxy group, and examples thereof include glycidyl ethers of aliphatic alcohols (including chain alcohols and alicyclic alcohols) or polyalkylene oxide adducts thereof, and hydrogenated bisphenol-type epoxy resins obtained by hydrogenating bisphenol-type epoxy resins such as bisphenol A-type epoxy resins and bisphenol F-type epoxy resins. Examples of aliphatic epoxy compounds include ethylene glycol diglycidyl ether, diethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, 1,4-butanediol diglycidyl ether, neopentyl glycol diglycidyl ether, 1,6-hexanediol diglycidyl ether, glycerin diglycidyl ether, trimethylolpropane triglycidyl ether (e.g., Epolite 100MF manufactured by Kyoeisha Chemical Co., Ltd.), polyethylene glycol diglycidyl ether, polybutylene glycol diglycidyl ether (e.g., jER manufactured by Mitsubishi Chemical Corporation), and the like. YX7400N, etc.), lauryl alcohol polyethylene glycol glycidyl ether (e.g., Denacol EX-171, etc., manufactured by Nagase ChemteX Corporation), diglycidyl ether of alicyclic diol (e.g., ADEKA RESIN EP-4088S and EP-4088L, manufactured by ADEKA Corporation), diglycidyl ether of polyalkylene oxide adduct of alicyclic diol, and hydrogenated bisphenol A diglycidyl ether (e.g., jER YX8000, etc., manufactured by Mitsubishi Chemical Corporation), but are not limited to these.

[0089] The epoxy equivalent of the (F) other epoxy compound is preferably 90 to 1000 g / eq, more preferably 120 to 800 g / eq, and even more preferably 150 to 500 g / eq.

[0090] The other epoxy compounds (F) may be used alone or in combination of two or more.

[0091] The content of the epoxy compound other than the (F) alicyclic epoxy compound in the resin composition is preferably 5 to 50 wt %, more preferably 10 to 40 wt %, and even more preferably 15 to 35 wt %, relative to the total weight of the resin composition. The content of the epoxy compound other than the (F) alicyclic epoxy compound in the resin composition is preferably 50 to 200 wt %, and more preferably 100 to 150 wt %, relative to 100 wt % of the (A) alicyclic epoxy compound.

[0092] In this embodiment, from the viewpoint of low-temperature curing property, the content of all epoxy compounds contained in the resin composition is preferably 100 to 1,300 parts by weight, more preferably 110 to 1,200 parts by weight, and even more preferably 120 to 1,100 parts by weight, per 100 parts by weight of the (B) oxetane compound. The total epoxy compounds is the sum of the (A) alicyclic epoxy compound and the (F) epoxy compounds other than the alicyclic epoxy compound.

[0093] (G) Coupling Agent The resin composition of this embodiment may contain (G) a coupling agent (hereinafter also referred to as "component (G)"), if desired, to the extent that the effects of the present invention are not impaired. The coupling agent has two or more different functional groups in the molecule, one of which is a functional group that chemically bonds with inorganic materials and the other is a functional group that chemically bonds with organic materials. By including a coupling agent in the resin composition, the adhesive strength of the resin composition to substrates and the like is improved.

[0094] Examples of coupling agents include, but are not limited to, silane coupling agents, aluminum coupling agents, titanium coupling agents, etc., depending on the type of functional group that chemically bonds with the inorganic material.

[0095] Examples of coupling agents include, but are not limited to, various coupling agents such as epoxy, amino, vinyl, methacrylic, acrylic, and mercapto coupling agents depending on the type of functional group that chemically bonds with the organic material. Among these, epoxy coupling agents containing an epoxy group are preferred from the viewpoint of moisture resistance reliability.

[0096] The coupling agents may be used alone or in combination of two or more.

[0097] When a coupling agent is added, the amount of the coupling agent added is preferably 0.01% by weight to 10% by weight, and more preferably 0.1% by weight to 5% by weight, relative to the total weight of the resin composition, from the viewpoint of improving adhesive strength.

[0098] (H) Pigment The resin composition of this embodiment may contain a (H) pigment (hereinafter also referred to as "component (H)") to the extent that the effects of the present invention are not impaired. Depending on the application of the cured product of the resin composition, light-blocking properties may be required. In such cases, the resin composition of this embodiment may contain a pigment. Examples of pigments include inorganic pigments such as carbon black, graphite, iron oxide, titanium black, anthraquinone, cobalt oxide, copper oxide, manganese, antimony oxide, nickel oxide, perylene, aniline, molybdenum sulfide, and bismuth sulfide, as well as organic pigments such as azo, cyanine, phthalocyanine, and quinacridone pigments. Examples of commercially available pigments include Titanium Black 13M, 13M-C, and 13MT manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd. The amount of pigment added can be determined appropriately depending on the application of the cured product of the resin composition.

[0099] Other Additives If desired, the resin composition of this embodiment may further contain other additives, such as organic peroxides, photosensitizers, conductive fillers, stabilizers, ion trapping agents, leveling agents, antioxidants, antifoaming agents, viscosity modifiers, flame retardants, colorants, plasticizers, solvents, etc. The type and amount of each additive are as per usual, provided that the purpose of this embodiment is not impaired.

[0100] From the viewpoint of preventing a reduction in curing strength and adhesion and preventing outgassing and bleeding, the resin composition of this embodiment is substantially free of liquid components such as water, solvents, ionic liquids, etc. (excluding the liquid components (A), (B), (D), and (F)). For example, the content of liquid components relative to the total weight of the resin composition is preferably 3 wt % or less, and more preferably 1 wt % or less. Examples of the solvent include organic solvents commonly used in the field of curable compositions, such as hydrocarbons (benzene, toluene, xylene, cyclohexane, etc.), aprotic polar solvents (N,N-dimethylformamide, dimethyl sulfoxide, N-methyl-2-pyrrolidone, etc.), nitriles (acetonitrile, etc.), ketones (acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, etc.), esters (ethyl acetate, butyl acetate, butyrolactone, propylene carbonate, etc.), ethers (cyclopentyl methyl ether, diethyl ether, tetrahydrofuran, dimethoxyethane, etc.), alcohols (methanol, ethanol, propanol, butanol, etc.), terpenes (turpentine, terpineol, isobornyl acetate, etc.), and halogenated solvents (dichloromethane, chloroform, etc.).

[0101] The method for producing the resin composition of this embodiment is not particularly limited. For example, the resin composition of this embodiment can be obtained by simultaneously or separately introducing components (A) to (D), and other optional components as needed, into an appropriate mixer, and stirring and mixing while melting by heating if necessary to form a homogeneous composition. The mixer is not particularly limited, but examples that can be used include a Raikai mixer, a Henschel mixer, a three-roll mill, a ball mill, a planetary mixer, and a bead mill equipped with a stirrer and a heater. These devices may also be used in appropriate combinations.

[0102] The resin composition of this embodiment can be a one-component resin composition contained in a single container, or a two-component (or multi-component) resin composition divided into two or more containers, depending on the intended use. When a two-component (or multi-component) resin composition is used, the components (A) to (D) and other optional components as needed can be selected in the same manner as for a one-component resin composition. Furthermore, when a two-component (or multi-component) resin composition is used, the components (A) to (D) and other optional components as needed can be divided into two or multiple components in any manner without particular limitation. When divided into two or multiple components in any manner, each component may contain one or more components selected from the components (A) to (D) and other optional components as needed. The components (A) to (D) may be contained in a single component, or a component may contain only the components (A) to (D) and / or other optional components as needed. For example, when separating into liquid A and liquid B, the separation may be as follows: liquid A: component (A), liquid B: component (B) and component (C) and component (D), or liquid A: component (A) and component (C), liquid B: component (B) and component (D), or liquid A: component (A) and component (D), or liquid B: component (B) and component (C), or liquid A: component (B), liquid B: component (A) and component (C) and component (D), or liquid A: component (A), component (B) and component (C), or liquid B: component (A), component (C) and component (D). When components (A) to (D) are contained in liquid A and other components are contained in liquid B, only liquid A, or a combination of liquid A and liquid B, can be considered the resin composition of this embodiment. On the other hand, when components (A) to (D) are contained in separate liquids, the respective liquids can be combined to form the resin composition of this embodiment. Examples of the case where the components (A) to (D) are contained in separate liquids include a resin composition in which the components (A) to (D) are separated into two or more containers, specifically a kit composed of multiple liquids containing any of the components (A) to (D).

[0103] The resin composition thus obtained is photocurable, thermosetting, or photo- and thermosetting, depending on the type of acid generator contained in the resin composition. When the resin composition is photocurable, the photocuring of the resin composition is carried out, for example, by irradiating the resin composition with UV light. When the resin composition is thermosetting, it is preferably cured within 5 hours, more preferably within 3 hours, and even more preferably within 1 hour at a temperature of 100°C. In one embodiment, for example, the resin composition of this aspect is thermally cured at a temperature of 70 to 100°C for 30 to 120 minutes. When the resin composition is photo- and thermosetting, it can be further cured with heat, for example, after preliminary curing with light (UV) or during light irradiation.

[0104] The resin composition of this embodiment can be used, for example, as an adhesive or sealant for fixing, joining or protecting semiconductor devices or electronic components or components constituting them, or as a raw material thereof.

[0105] The method for applying the resin composition is not particularly limited, and for example, the resin composition can be applied to a desired portion of a component such as a substrate by a known printing method, dispensing method, or coating method. Printing methods include, but are not limited to, inkjet printing, screen printing, lithographic printing, carton printing, metal printing, offset printing, gravure printing, and flexographic printing. Dispensing methods include, but are not limited to, methods using a jet dispenser or an air dispenser. Coating methods include, but are not limited to, dip coating, spray coating, bar coater coating, gravure coating, reverse gravure coating, and spin coater coating.

[0106] [Adhesive or Sealant] Another embodiment of the present invention is an adhesive or sealant that includes the resin composition of the above-described embodiment. This adhesive or sealant provides excellent fixation, bonding, or protection for general-purpose plastics (e.g., PE, PS, PP, etc.), engineering plastics (e.g., LCP (liquid crystal polymer), polyamide, polycarbonate, polyphthalamide, polybutylene terephthalate, etc.), glass, ceramics, metals (e.g., copper, nickel, etc.), and organic substrates (e.g., FR4, etc.), and can be used to fix, bond, or protect components that make up a semiconductor device or electronic component. Examples of semiconductor devices include, but are not limited to, HDDs, semiconductor elements, sensor modules such as image sensor modules and time-of-flight sensor modules, other semiconductor modules, and integrated circuits.

[0107] The adhesive or sealant of this embodiment can be a one-component adhesive or sealant contained in a single container, or a two-component (or multi-component) adhesive or sealant divided into two or more containers, depending on its intended use. When a two-component (or multi-component) adhesive or sealant is used, the components (A) to (D) and other optional components as needed can be selected in the same manner as for a one-component adhesive or sealant. Furthermore, when a two-component (or multi-component) adhesive or sealant is used, the components (A) to (D) and other optional components as needed can be divided into two or multiple components in any manner without particular limitation. When divided into two or multiple components in any manner, each component may contain one or more components selected from the components (A) to (D) and other optional components as needed. The components (A) to (D) may be contained in a single component, or a component may contain only the components (A) to (D) and / or other optional components as needed. For example, when the liquid is divided into liquid A and liquid B, the division may be liquid A: component (A), liquid B: component (B), component (C), and component (D), or liquid A: component (A) and component (C), liquid B: component (B) and component (D), or liquid A: component (A) and component (D), liquid B: component (B) and component (C), or liquid A: component (B), liquid B: component (A), component (C), and component (D), or liquid A: component (A), component (B), and component (C), or liquid B: component (A), component (C), and component (D). When components (A) to (D) are contained in liquid A and other components are contained in liquid B, liquid A alone, or a combination of liquid A and liquid B, can be considered the adhesive or sealant of this embodiment. On the other hand, when components (A) to (D) are contained in separate liquids, the respective liquids can be considered together to be the adhesive or sealant of this embodiment. Examples of the case where the components (A) to (D) are contained in separate liquids include an adhesive or sealant in which the components (A) to (D) are separated into two or more containers, and specifically, a kit composed of multiple liquids containing any of the components (A) to (D).

[0108] [Cured Product of Resin Composition, Adhesive, or Sealant] Another embodiment of the present invention is a cured product obtained by curing the resin composition, adhesive, or sealant of the above-described embodiment. This cured product has excellent high-temperature, high-humidity reliability. That is, even after this cured product is placed in a high-temperature, high-humidity environment for a long period of time, specifically, the change in Tg of the cured product before and after a pressure cooker test (PCT) under conditions of 2 atm, 121°C, 100% RH, and 20 hours is small. In this embodiment, the change in Tg of the cured product before and after a PCT under conditions of 2 atm, 121°C, 100% RH, and 20 hours is preferably less than 10.3°C, more preferably 8°C or less, and even more preferably 6°C or less.

[0109] [Semiconductor Device, Electronic Component] Another aspect of the present invention is a semiconductor device or electronic component that includes the cured product of the above-described aspect. Here, the term "semiconductor device" refers to any device that can function by utilizing semiconductor properties, including electronic components, semiconductor circuits, modules incorporating these, electronic devices, etc. Examples of semiconductor devices or electronic components include, but are not limited to, HDDs, semiconductor elements, sensor modules such as image sensor modules and time-of-flight (TOF) sensor modules, other semiconductor modules, and integrated circuits.

[0110] The present invention will be described in more detail below with reference to examples and comparative examples, but the present invention is not limited to these examples. In the following examples, parts and percentages are by weight unless otherwise specified.

[0111] [Production of Resin Composition] Resin compositions of the Examples and Comparative Examples were prepared by mixing predetermined amounts of each component using a three-roll mill according to the formulations shown in Table 1. In Table 1, the amount of each component is expressed in parts by weight (unit: g). The components used in the Examples and Comparative Examples are as follows.

[0112] (A) Alicyclic epoxy compound (A-1): 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate (product name: CELLOXIDE (registered trademark) 2021P, manufactured by Daicel Corporation, epoxy equivalent: 130 g / eq) (B) Oxetane compound (B-1): 3-ethyl-3{[(3-ethyloxetan-3-yl)methoxy]methyl}oxetane (product name: OXT-221, manufactured by Toagosei Co., Ltd., oxetane equivalent: 107 g / eq) (C) Filler (C-1): Hydrophobic fumed silica (product name: CAB-O-SIL (registered trademark) TS720, manufactured by CABOT Corporation, average particle size: 12 nm) (C-2): Surface-treated silica filler (product name: SE5200SEE, average particle size 2 μm, manufactured by Admatechs Co., Ltd.)

[0113] (D) Acid generators which are salts of a gallate anion of formula (1) and a counter cation other than an iodonium cation (in the table, this is indicated as "(D) Gallate-based acid generator (other than an iodonium cation)"). (D1-1): Thermal acid generators represented by the following formula: This thermal acid generator was synthesized by the method described in WO 2018 / 020974. (D2-1): Photoacid generator represented by the following formula: This photoacid generator was synthesized by the method described in WO 2018 / 020974. (E) Acid generator other than component (D) (E-1): Thermal acid generator represented by the following formula (Product name: TA-100, manufactured by San-Apro Co., Ltd.) (E-2): A thermal acid generator represented by the following formula: These thermal acid generators were synthesized by the method described in JP 2022-080366 A. (E-3): Borate-based quaternary ammonium salt (product name: CXC-1821, manufactured by King Industries, Inc., thermal acid generator) (E-4): Borate-based sulfonium salt (product name: CPI-310B, manufactured by San-Apro Co., Ltd., photoacid generator)

[0114] (F) Epoxy compounds other than alicyclic epoxy compounds (F-1): Polypropylene oxide-modified bisphenol A epoxy resin (product name: AER9000, manufactured by Asahi Kasei Corporation, epoxy equivalent: 380 g / eq) (F-2): p-tert-butylphenyl glycidyl ether (product name: ADEKA GLYCILOR (registered trademark) ED-509S, manufactured by ADEKA Corporation, epoxy equivalent: 205 g / eq) (G) Coupling agent (G-1): 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane (product name: KBM-303, manufactured by Shin-Etsu Chemical Co., Ltd.) (H) Pigment (H-1): Titanium black (product name: 13M, manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd.) (I) Other additives (I-1): Dicetyl peroxydicarbonate (product name: Perkadox (registered trademark) 24L, manufactured by Nouryon)

[0115] [Production of Cured Product] Each of the resin compositions of the Examples and Comparative Examples was heated at 100°C for 60 minutes to produce a cured product.

[0116] In the examples and comparative examples, the properties of the resin compositions and their cured products were measured as follows.

[0117] [Measurement of Tg and Elastic Modulus of Cured Product Before and After PCT] Each resin composition was applied to a glass substrate to a thickness of 250±100 μm, and the sample was subjected to a thermal curing treatment by heating at 100°C for 60 minutes in a fan dryer to produce a cured product on the glass substrate. The cured product was subjected to dynamic thermomechanical analysis (DMA) to determine the initial Tg [°C] and elastic modulus [GPa] at 25°C of the cured product. The cured product was then subjected to PCT under conditions of 2 atm, 121°C, 100% RH, and 20 hours, and the Tg [°C] and elastic modulus [GPa] of the cured product after PCT were determined. The change in Tg of the cured product before and after PCT was calculated using the following equation. [Change in Tg of cured product before and after PCT] = |[Initial Tg of cured product] - [Tg of cured product after PCT]| The elastic modulus was measured at 25°C using a dynamic viscoelasticity measuring (DMA) device manufactured by Hitachi, Ltd. in accordance with Japanese Industrial Standard JIS C6481. The Tg was measured using a dynamic viscoelasticity measuring (DMA) device manufactured by Hitachi, Ltd. in accordance with Japanese Industrial Standard JIS C6481. The results are shown in Table 1. In this specification, the change in Tg of the cured product before and after PCT under conditions of 2 atm, 121°C, 100% RH, and 20 hours is preferably less than 10.3°C, more preferably 8°C or less, and even more preferably 6°C or less.

[0118]

[0119] The cured products of the resin compositions of Examples 1 to 9, which satisfy the configuration of the present invention, showed a small change in Tg before and after PCT. On the other hand, the cured products of the resin compositions of Comparative Examples 1 to 4, which did not contain an acid generator that is a salt of a gallate anion of formula (1) (D) and a counter cation other than an iodonium cation, but contained an acid generator other than component (D) (E), showed a large change in Tg before and after PCT. Surprisingly, the cured product of the resin composition of Example 9, which contained an acid generator other than component (D) (E) in addition to an acid generator that is a salt of a gallate anion of formula (1) (D) and a counter cation other than an iodonium cation, showed a small change in Tg before and after PCT, even though it contained an acid generator other than component (D) (E). The cured product of the resin composition of Comparative Example 5, which did not contain an oxetane compound (B), also showed a large change in Tg before and after PCT. Although not shown in Table 1, a similar evaluation was also performed on a two-component resin composition in Example 2, in which component A was component (A), component (C), component (F), component (G), and component (H), and component B was component (B) and component (D), and the results were similar to those of the one-component resin composition.

[0120] The resin composition of the present invention is very useful, for example, as an adhesive or sealant for fixing, joining or protecting semiconductor devices or electronic components or components constituting them, or as a raw material thereof.

[0121] The disclosure of Japanese Patent Application No. 2024-048038 (filing date: March 25, 2024) is incorporated herein by reference in its entirety. All documents, patent applications, and technical standards mentioned herein are incorporated herein by reference to the same extent as if each individual document, patent application, and technical standard was specifically and individually indicated to be incorporated by reference.

Claims

1. (A) an alicyclic epoxy compound, (B) an oxetane compound, (C) a filler, and (D) a compound represented by the following formula (1): (In the formula, R １ , R ２ , R ３ and R ４ each independently represents an alkyl group having 1 to 18 carbon atoms or an aryl group having 6 to 14 carbon atoms, provided that R １ , R ２ , R ３ and R ４ and a counter cation other than an iodonium cation.

2. The resin composition according to claim 1, wherein the acid generator (D) is a thermal acid generator (D1).

3. The resin composition according to claim 1, wherein the acid generator (D) is a photoacid generator (D2).

4. The resin composition according to claim 1, wherein the acid generator (D) is a combination of a thermal acid generator (D1) and a photoacid generator (D2).

5. The resin composition according to any one of claims 1 to 4, wherein the counter cation in the acid generator (D) is a sulfonium cation or an ammonium cation.

6. The resin composition according to any one of claims 1 to 5, wherein the content of the acid generator (D) is 0.1 to 10 parts by weight per 100 parts by weight of the total amount of the resin composition.

7. The resin composition according to any one of claims 1 to 6, further comprising (E) an acid generator other than component (D).

8. The resin composition according to claim 7, wherein the acid generator (E) other than component (D) contains a sulfonium cation or an ammonium cation.

9. The resin composition according to any one of claims 1 to 8, further comprising (F) an epoxy compound other than an alicyclic epoxy compound.

10. The resin composition according to claim 9, wherein the epoxy compound (F) other than the alicyclic epoxy compound comprises an epoxy compound having an epoxy equivalent of 90 to 1000 g / eq.

11. The resin composition according to claim 9 or 10, wherein the content of the epoxy compound other than the (F) alicyclic epoxy compound is 50 to 200 parts by weight per 100 parts by weight of the (A) alicyclic epoxy compound.

12. A resin composition according to any one of claims 1 to 11, wherein the total content of the epoxy compounds contained in the resin composition is 100 to 1,300 parts by weight per 100 parts by weight of the oxetane compound (B).

13. The resin composition according to any one of claims 1 to 12, wherein components (A) to (D) are contained in a single container.

14. The resin composition according to any one of claims 1 to 12, wherein components (A) to (D) are separated into two or more containers.

15. An adhesive or sealant comprising the resin composition according to any one of claims 1 to 14.

16. A cured product obtained by curing the resin composition according to any one of claims 1 to 14, or the adhesive or sealant according to claim 15.

17. A semiconductor device or electronic component comprising the cured product according to claim 16.

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