[go: up one dir, main page]

WO2025204845A1 - Composition de résine, agent adhésif, matériau d'étanchéité, produit durci, dispositif à semi-conducteur et composant électronique - Google Patents

Composition de résine, agent adhésif, matériau d'étanchéité, produit durci, dispositif à semi-conducteur et composant électronique

Info

Publication number
WO2025204845A1
WO2025204845A1 PCT/JP2025/008984 JP2025008984W WO2025204845A1 WO 2025204845 A1 WO2025204845 A1 WO 2025204845A1 JP 2025008984 W JP2025008984 W JP 2025008984W WO 2025204845 A1 WO2025204845 A1 WO 2025204845A1
Authority
WO
WIPO (PCT)
Prior art keywords
resin composition
group
component
cured product
components
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
PCT/JP2025/008984
Other languages
English (en)
Japanese (ja)
Inventor
文也 鈴木
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Namics Corp
Original Assignee
Namics Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Namics Corp filed Critical Namics Corp
Publication of WO2025204845A1 publication Critical patent/WO2025204845A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
    • C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
    • C08G65/16—Cyclic ethers having four or more ring atoms
    • C08G65/18—Oxetanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
    • C08K3/013—Fillers, pigments or reinforcing additives
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/56—Organo-metallic compounds, i.e. organic compounds containing a metal-to-carbon bond
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L23/00—Details of semiconductor or other solid state devices
    • H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
    • H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L23/00—Details of semiconductor or other solid state devices
    • H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
    • H01L23/31—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the arrangement or shape

Definitions

  • the present invention relates to a resin composition, an adhesive or sealant containing the same, a cured product thereof, and a semiconductor device and electronic component containing the cured product.
  • curable resin compositions particularly epoxy resin compositions
  • adhesives, sealants, etc. containing curable resin compositions are often used in the assembly and mounting of semiconductor devices and electronic components, such as semiconductor chips, in order to maintain reliability.
  • Patent Document 1 discloses a cationic curable resin composition that contains a cationic polymerizable compound, a photocationic polymerization initiator, and a thermal cationic polymerization initiator containing an amine salt, as a cationic curable resin composition that maintains photocurability and low-temperature curability while also being storage stable.
  • Patent Document 2 also discloses a UV/thermal curable adhesive composition that does not use an antimony compound as a thermal cationic polymerization initiator, is low in toxicity, can be cured at low temperatures of 120°C or less, and produces a cured product with excellent heat resistance.
  • the composition contains specific amounts of an oxetane compound, an alicyclic epoxy compound, an aromatic glycidyl ether epoxy compound, a photocationic polymerization initiator, and a thermal cationic polymerization initiator containing a tetrakis(pentafluorophenyl)borate compound.
  • a subsequent process such as reflow may be carried out, placing the module in a high-temperature environment (e.g., 200°C or higher). Therefore, the cured product of the curable resin composition used for assembly and installation must be heat-resistant enough to withstand the reflow process.
  • the present invention aims to provide a resin composition that can be cured at least by light or at low temperatures (e.g., 100°C or below) and that produces a cured product with excellent adhesive strength and heat resistance reliability, an adhesive or sealant containing the same, a cured product thereof, and a semiconductor device and electronic component containing the cured product.
  • a resin composition that can be cured at least by light or at low temperatures (e.g., 100°C or below) and that produces a cured product with excellent adhesive strength and heat resistance reliability, an adhesive or sealant containing the same, a cured product thereof, and a semiconductor device and electronic component containing the cured product.
  • the present invention encompasses the following curable resin composition, adhesive or sealant, cured product, and semiconductor device or electronic component.
  • R 1 , R 2 , R 3 and R 4 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 R 1 , R 2 , R 3 and R 4 represents an aryl group having 6 to 14 carbon atoms.
  • the content of the (A) epoxy compound is 100 to 1,300 parts by weight based on 100 parts by weight of the (B) oxetane compound; Resin composition.
  • a resin composition that can be cured at least by light or at low temperatures (for example, 100°C or less) and that produces a cured product with excellent adhesive strength and heat resistance reliability, an adhesive or sealant containing the same, a cured product thereof, and a semiconductor device and electronic component containing the cured product.
  • the term "resin,” which normally refers to a polymer (especially a synthetic polymer), may be used to refer to the components that make up a curable resin composition before curing, even when the component is not a polymer, for example, a monomer or prepolymer compound before curing.
  • the resin composition comprises: (A) an epoxy compound, (B) an oxetane compound, and (C) a compound of the following formula (1): (In the formula, R 1 , R 2 , R 3 and R 4 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 R 1 , R 2 , R 3 and R 4 represents an aryl group having 6 to 14 carbon atoms.) and a counter cation, and Satisfy at least one of the following characteristics (a) and (b): (a) further comprising (D) a filler; (b)
  • the content of the (A) epoxy compound is 100 to 1,300 parts by weight based on 100 parts by weight of the (B) oxetane compound.
  • a resin composition that can be at least photocured or cured at a low temperature (for example, 100°C or lower
  • Epoxy Compound The resin composition of this embodiment contains (A) an epoxy compound (hereinafter also referred to as "component (A)").
  • an epoxy compound refers to a compound having at least one epoxy group in the molecule, and examples thereof include monofunctional epoxy compounds having one epoxy group and polyfunctional epoxy compounds having two or more epoxy groups.
  • the epoxy compound contains at least a polyfunctional epoxy compound, and may contain a combination of a polyfunctional epoxy compound and a monofunctional epoxy compound.
  • Epoxy compounds can be broadly classified into epoxy compounds having an aromatic ring skeleton, aliphatic epoxy compounds, and alicyclic epoxy compounds, depending on the type of skeleton.
  • epoxy compounds having an aromatic ring skeleton include polyfunctional epoxy resins such as: Bisphenol A type epoxy resins (for example, EPICLON (registered trademark) 850, 850-S, EXA-850CRP, EXA-8067 manufactured by DIC Corporation, etc.), Polyalkylene oxide-modified bisphenol A type epoxy resins, for example, polypropylene oxide-modified bisphenol A type epoxy resins (for example, AER9000 manufactured by Asahi Kasei Corporation, EP-4000S, EP-4003S, EP-4005, and EP-4010S manufactured by ADEKA Corporation), polyethylene oxide-modified bisphenol A type epoxy resins (for example, Rikaresin BEO-60E manufactured by New Japan Chemical Co., Ltd.), Bisphenol F type epoxy resins (for example, EPICLON (registered trademark) 830-S, EXA-830LVP, EXA-835LV manufactured by DIC Corporation), - bisphenol AD type epoxy resin, - bisphenol S type epoxy resin, - bis
  • Cresol novolac epoxy resin such as EPICLON (registered trademark) N-660, N-670, and N-655-EXP-S manufactured by DIC Corporation
  • polyfunctional epoxy compounds such as glycidyl ethers of tetra(hydrophenyl)alkanes and glycidyl ethers of tetrahydroxybenzophenone
  • monofunctional epoxy compounds having a polyaromatic 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.).
  • 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.
  • the alicyclic epoxy compound preferably has 2 to 6 alicyclic epoxy groups, and even more preferably has 2 alicyclic epoxy groups.
  • alicyclic epoxy compounds include 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.
  • the epoxy equivalent of the alicyclic epoxy compound is preferably 90 to 1000 g/eq, more preferably 100 to 800 g/eq, even more preferably 100 to 500 g/eq, and particularly preferably 110 to 300 g/eq.
  • the amount of the epoxy compound having a polyalkylene oxide chain, an aliphatic moiety derived from an alicyclic diol, an aliphatic moiety derived from hydrogenated bisphenol A, or a combination thereof, relative to 100 parts by weight of the total epoxy compounds is preferably 20 to 100 parts by weight, more preferably 30 to 100 parts by weight, and even more preferably 40 to 100 parts by weight. In one embodiment, the amount of the epoxy compound having a polyalkylene oxide chain is preferably 10 to 100 parts by weight, more preferably 15 to 100 parts by weight, relative to 100 parts by weight of the total epoxy compounds.
  • 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.
  • the polymerization initiation reaction of an oxetane compound is slower than that of an 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 and in a short time.
  • the adhesive strength of the cured product is improved.
  • 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.
  • 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 compounds 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 of the oxetane compounds may be used alone, or two or more may be used in combination.
  • the content of the (B) oxetane compound in the resin composition is preferably 1 to 60 parts by weight, and more preferably 5 to 50 parts by weight, per 100 parts by weight of the total amount of the resin composition.
  • the acid generator generates an acid as an active species in response to light or heat, thereby promoting polymerization of the cationically polymerizable compound.
  • an acid generator which is a salt composed of an anion represented by formula (1) (hereinafter also referred to as "gallate anion") and a counter cation
  • the resin composition can be cured at least by light or at a low temperature (for example, 100°C or lower) and can give a cured product with excellent heat resistance reliability.
  • Commonly known acid generators contain BF 4 ⁇ , PF 6 ⁇ , AsF 6 ⁇ , or SbF 6 ⁇ as the anion moiety.
  • the strength of the acid generated by an acid generator depends on the anion moiety. It is believed that the stronger the acid generated by an acid generator, the higher the polymerization activity for cationic polymerization, with the strength of the generated acid in the following order: BF 4 ⁇ ⁇ PF 6 ⁇ ⁇ AsF 6 ⁇ ⁇ SbF 6 ⁇ .
  • the gallate anion in the acid generator (C) of this embodiment generates a strong acid, but has lower thermal stability than the borate anion and decomposes at high temperatures.
  • the decomposition product may generate a weak acid, it does not induce decomposition of the cured product, thereby suppressing a decrease in the Tg and elastic modulus of the cured product. As a result, a cured product of the resin composition with excellent heat resistance reliability can be obtained.
  • R 1 , R 2 , R 3 and R 4 each independently represent an alkyl group having 1 to 18 carbon atoms or an aryl group having 6 to 14 carbon atoms, but at least one of R 1 , R 2 , R 3 and R 4 represents an aryl group having 6 to 14 carbon atoms. That is, R 1 , R 2 , R 3 and R 4 in formula (1) are any of the following combinations: (i) A combination in which one of R 1 , R 2 , R 3 and R 4 is an aryl group and the remaining three are alkyl groups. (ii) A combination in which two of R 1 , R 2 , R 3 and R 4 are aryl groups and the remaining two are alkyl groups.
  • the alkyl group having 1 to 18 carbon atoms represented by 4 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,
  • the alkyl groups having 1 to 18 carbon atoms represented by R 1 , R 2 , R 3 and R 4 in formula (1) may have a substituent.
  • substituted alkyl group used here refers to an alkyl group in which a hydrogen atom in the structure of the alkyl group is substituted with a substituent, and the position and number of the substituent are not particularly limited. Note that when the substituent has a carbon atom, the number of carbon atoms in the alkyl group represented by R 1 , R 2 , R 3 and R 4 does not include the number of carbon atoms in the substituent.
  • an ethyl group having a phenyl group as a substituent is an alkyl group having 2 carbon atoms.
  • the aromatic group that may be substituted on the alkyl group having 1 to 18 carbon atoms represented by R 1 , R 2 , R 3 and R 4 in formula (1) 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.
  • 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.
  • Examples include sulfolinium, piperidinium such as N,N'-diethylpiperidinium, 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.
  • the content of the acid generator (C) in the resin composition is preferably 0.1 to 10 parts by weight, and more preferably 0.3 to 8 parts by weight, per 100 parts by weight of the total amount of the resin composition.
  • the content of the acid generator (C) in the resin composition is preferably 0.1 to 20 parts by weight, and 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 epoxy compound (A) and the oxetane compound (B).
  • the resin composition of this embodiment satisfies at least one of the following characteristics (a) and (b): (a) further comprising (D) a filler; (b)
  • the content of the (A) epoxy compound is 100 to 1,300 parts by weight per 100 parts by weight of the (B) oxetane compound, thereby providing a resin composition that gives a cured product with excellent adhesive strength.
  • the resin composition of this embodiment contains a filler (hereinafter also referred to as “component (D)”), which can improve the fluidity, injectability, coatability, adhesion, etc. of the resin composition, thereby providing a cured product with excellent adhesive strength.
  • Fillers are broadly classified into inorganic fillers and organic fillers.
  • the inorganic filler is not particularly limited as long as it is made of granular 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.
  • Silica filler is preferred as the inorganic filler, as it allows for a high loading.
  • Amorphous silica is preferred as the silica.
  • the surface of the inorganic filler may be treated with a coupling agent such as a silane coupling agent.
  • organic fillers examples include polytetrafluoroethylene (PTFE) fillers, silicone fillers, acrylic fillers, fillers with a urethane skeleton, fillers with a butadiene skeleton, and styrene fillers.
  • PTFE polytetrafluoroethylene
  • silicone fillers acrylic fillers
  • fillers with a urethane skeleton fillers with a butadiene skeleton
  • styrene fillers examples include polytetrafluoroethylene (PTFE) fillers, silicone fillers, acrylic fillers, fillers with a urethane skeleton, fillers with a butadiene skeleton, and styrene fillers.
  • the organic fillers may be surface-treated.
  • the shape of the filler is not particularly limited and may be spherical, flaky, needle-like, irregular, etc.
  • 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 ⁇ m or more, and more preferably 0.01 ⁇ m or more. In some embodiments of this aspect, the average particle size of the filler is preferably 0.01 ⁇ m to 5.0 ⁇ m, more preferably 0.1 ⁇ m to 3.0 ⁇ m. Fillers with different average particle sizes may be used in combination. For example, a filler having an average particle size of 0.005 ⁇ m or more and less than 0.1 ⁇ m and a filler having an average particle size of 0.1 ⁇ m to 6.0 ⁇ m may be used in combination.
  • the content of filler (D) in the resin composition is preferably 15 to 50 parts by weight, more preferably 20 to 50 parts by weight, and even more preferably 30 to 50 parts by weight, per 100 parts by weight of the total amount of the resin composition.
  • the content of the (A) epoxy compound is 100 to 1,300 parts by weight per 100 parts by weight of the (B) oxetane compound, thereby improving the adhesion of the resin composition and providing a cured product with excellent adhesive strength, even in an embodiment that does not contain the (D) filler.
  • the content of the (A) epoxy compound is preferably 200 to 1,300 parts by weight, and more preferably 300 to 1,250 parts by weight per 100 parts by weight of the (B) oxetane compound.
  • the resin composition of this aspect satisfies the above characteristic (a). In one embodiment, the resin composition of this aspect satisfies the characteristic (b). In one embodiment, the resin composition of this aspect satisfies the above characteristics (a) and (b).
  • the resin composition of this aspect satisfies the characteristic (a) and contains 5 to 100 parts by weight of the (D) filler, preferably 20 to 90 parts by weight, and more preferably 30 to 80 parts by weight, per 100 parts by weight of the total of the (A) epoxy compound and the (B) oxetane compound.
  • the resin composition of this embodiment may, if desired, further comprise the above-mentioned components (A) to (C) or (A) to (C).
  • Optional components other than (D), such as those described below, may be contained as necessary.
  • the resin composition of this embodiment may contain (E) a photosensitizer (hereinafter also referred to as "component (E)”), if desired, to the extent that the effects of the present invention are not impaired.
  • the photosensitizer absorbs light energy and transmits it to the acid generator, thereby increasing the sensitivity of the acid generator to light.
  • Examples of photosensitizers include thioxanthone derivatives, carbonyl compounds, organic sulfur compounds, persulfides, redox compounds, azo and diazo compounds, halogen compounds, and photoreducible dyes, with thioxanthone derivatives being preferred.
  • thioxanthone derivatives include isopropylthioxanthone, 2,4-diethylthioxanthone, 2-chlorothioxanthone, 2,4-diethylthioxanthone, 2-chlorothioxanthone, and thioxanthone ammonium salt, with 2,4-diethylthioxanthone being preferred.
  • photosensitizers include 9-fluorenone, anthrone, dibenzosuberone, fluorene, 2-bromofluorene, 9-bromofluorene, 9,9-dimethylfluorene, 2-fluorofluorene, 2-iodofluorene, 2-fluorenamine, 9-fluorenol, 2,7-dibromofluorene, 9-aminofluorene hydrochloride, 2,7-diaminofluorene, 9,9'-spirobi[9H-fluorene], 2-fluorenecarboxaldehyde, 9-fluorenylmethanol, 2-acetylfluorene, benzophenone, diethoxyacetophenone, 2- Examples include, but are not limited to, hydroxy-2-methyl-1-phenylpropan-1-one, benzyl dimethyl ketal, 4-(2-hydroxyethoxy)phenyl-(2-hydroxy-2-propyl)
  • the content of the photosensitizer is preferably 0.1 to 20 parts by weight, and more preferably 1 to 15 parts by weight, per 100 parts by weight of the acid generator.
  • the resin composition of this embodiment may contain (F) a photoradical initiator (hereinafter also referred to as "component (F)”), if desired, within a range that does not impair the effects of the present invention.
  • the photoradical initiator absorbs light to generate radicals as active species, which can reductively decompose the acid generator and promote the generation of acid from the acid generator.
  • Examples of photoradical initiators include, but are not limited to, alkylphenone compounds, acylphosphine oxide compounds, oxime ester compounds, and compounds having a photosensitive moiety and a peroxide structure.
  • alkylphenone compounds include benzyl dimethyl ketals such as 2,2-dimethoxy-1,2-diphenylethan-1-one (commercially available as Omnirad 651, manufactured by IGM Resins B.V.); ⁇ -aminoalkylphenones such as 2-methyl-2-morpholino(4-thiomethylphenyl)propan-1-one (commercially available as Omnirad 907, manufactured by IGM Resins B.V.); 1-hydroxy-cyclohexyl-phenyl-ketone (commercially available as IGM Resins B.V.); Examples of suitable hydroxyalkyl phenones include, but are not limited to, ⁇ -hydroxyalkylphenones such as Omnirad 184 (manufactured by IGM Resins B.V.); 2-dimethylamino-2-(4-methyl-benzyl)-1-(4-morpholin-4-yl-phenyl)-butan-1-one (commercially available as Omnirad 379EG (manufacture
  • acylphosphine oxide compounds include, but are not limited to, 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide (commercially available as Omnirad TPO H, manufactured by IGM Resins B.V.) and bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide (commercially available as Omnirad 819, manufactured by IGM Resins B.V.). These compounds may be used alone or in combination of two or more.
  • oxime ester compounds include, but are not limited to, 1,2-octanedione, 1-[4-(phenylthio)-, 2-(O-benzoyloxime)] (trade name: Irgacure OXE-01, manufactured by BASF), ethanone, 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-, 1-(O-acetyloxime) (trade name: Irgacure OXE-02, manufactured by BASF), methanone, ethanone, 1-[9-ethyl-6-(1,3-dioxolane, 4-(2-methoxyphenoxy)-9H-carbazol-3-yl]-, 1-(O-acetyloxime) (trade name: ADEKA OPT-N-1919, manufactured by ADEKA Corporation).
  • Examples include, but are not limited to, tar, benzophenone, benzoylbenzoic acid, methyl benzoylbenzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, 3,3'-dimethyl-4-methoxybenzophenone, thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, 2,4-dimethylthioxanthone, isopropylthioxanthone, 2,4-dichlorothioxanthone, 2,4-diethylthioxanthone, 2,4-diisopropylthioxanthone, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, methylphenyl glyoxylate, benzil, and camphorquinone. These may be used alone or in combination of two or more.
  • the resin composition of this embodiment may further contain other additives, such as a conductive filler, a stabilizer, an ion trapping agent, a leveling agent, an antioxidant, an antifoaming agent, a viscosity modifier, a flame retardant, a colorant, a plasticizer, a solvent, etc.
  • additives such as a conductive filler, a stabilizer, an ion trapping agent, a leveling agent, an antioxidant, an antifoaming agent, a viscosity modifier, a flame retardant, a colorant, a plasticizer, a solvent, etc.
  • additives such as a conductive filler, a stabilizer, an ion trapping agent, a leveling agent, an antioxidant, an antifoaming agent, a viscosity modifier, a flame retardant, a colorant, a plasticizer, a solvent, etc.
  • the type and amount of each additive are as per usual, provided that the purpose of the embodiment is not impaired.
  • the resin composition of this embodiment is substantially free of liquid components such as water, solvents, ionic liquids, etc. (excluding liquid components (A) to (C)).
  • liquid components such as water, solvents, ionic liquids, etc.
  • the content of liquid components is preferably 3% by weight or less, and more preferably 1% by weight or less, relative to the total weight of the resin composition.
  • solvents 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, terpin
  • the method for producing the resin composition of this embodiment is not particularly limited.
  • the resin composition of this embodiment can be obtained by simultaneously or separately introducing components (A) to (C) or 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, Henschel mixer, three-roll mill, ball mill, planetary mixer, and bead mill equipped with a stirring device and a heating device. Appropriate combinations of these devices may also be used.
  • 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.
  • a two-component (or multi-component) resin composition is used, the components (A) to (C) or (A) to (D), and other optional components as needed, can be selected in the same way as for a one-component resin composition.
  • each liquid may contain one or more components selected from the components (A) to (C) or the components (A) to (D) and other optional components as required, the components (A) to (C) or the components (A) to (D) may be contained in one liquid, or there may be a liquid consisting only of the components (A) to (C) or the components (A) to (D) and/or other optional components as required.
  • the separation 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), liquid A: component (A) and component (C), liquid B: component (B), liquid A: component (A), liquid B: component (B), component (C), and component (D), liquid A: component (A) and component (C), liquid B: component (B) and component (D), liquid A: component (A) and component (D), liquid B: component (B) and component (C).
  • Liquid A alone, or a combination of Liquid A and Liquid B
  • the respective liquids can be considered together to be the resin composition of this embodiment.
  • An example of a case in which components (A) to (C) or components (A) to (D) are contained in separate liquids is a resin composition in which components (A) to (C) or components (A) to (D) are separated into two or more containers, specifically a kit composed of multiple liquids containing any of components (A) to (C) or components (A) to (D).
  • the resin composition obtained in this manner may be photocurable, thermocurable, or photo- and thermo-curable, depending on the type of acid generator contained in the resin composition.
  • the photocuring of the resin composition is carried out, for example, by irradiating the resin composition with UV light.
  • the resin composition is thermocurable, it preferably cures 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. If the resin composition is photo- and thermocurable, it can be further cured with heat, for example, after curing with light (UV) or during light irradiation.
  • UV light
  • the resin composition of this embodiment inhibits decomposition of the cured product, and inhibits a decrease in the Tg and modulus of elasticity of the cured product, even when the cured product is placed in a high-temperature environment (e.g., 200°C or higher) such as during a reflow process. Decomposition of the cured product in a high-temperature environment can be confirmed by DSC measurement.
  • a high-temperature environment e.g. 200°C or higher
  • the resin composition of this embodiment is heated from 25°C to 250°C at a heating rate of 10°C/min using a differential scanning calorimeter, it is preferable that the heat generation amount in the temperature range from 200°C to 250°C is 10 J/g or less.
  • the Tg of the cured product obtained by photocuring and/or heat curing at a temperature of 100°C or less is preferably 10 to 150°C, more preferably 20 to 120°C, and even more preferably 25 to 90°C. This results in smaller changes in the glass transition temperature Tg and elastic modulus of the cured product, even when the cured product of the resin composition is placed in a high-temperature environment.
  • the modulus of elasticity of the cured product obtained by photocuring and/or heat curing at a temperature of 100°C or less is preferably 0.01 to 5 GPa, more preferably 0.1 to 4 GPa, and even more preferably 0.2 to 3.8 GPa. This results in smaller changes in the glass transition temperature Tg and modulus of elasticity of the cured product, even when the cured product of the resin composition is placed in a high-temperature environment.
  • 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 the components that make them up, or as a raw material for such adhesives or sealants.
  • the method for applying the resin composition is not particularly limited, and for example, it can be applied to the 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 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.
  • 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 enables good fixation, bonding, or protection of 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, and metals (e.g., copper, nickel, SUS, etc.), and organic substrates (e.g., FR4, etc.), and can be used to fix, bond, or protect components that make up semiconductor devices or electronic components.
  • 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.
  • 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 separated into two or more containers.
  • a two-component (or multi-component) adhesive or sealant is used, the components (A) to (C) or (A) to (D), and other optional components as needed, can be selected in the same manner as for a one-component adhesive or sealant.
  • the components (A) to (C) or (A) to (D), and other optional components as needed can be separated into two or more components in any manner without particular restriction, but it is preferable to separate component (C) from component (E) and/or component (F) and/or component (H) as separate components.
  • each liquid may contain one or more components selected from the components (A) to (C) or the components (A) to (D) and other optional components as required, the components (A) to (C) or the components (A) to (D) may be contained in one liquid, or there may be a liquid consisting only of the components (A) to (C) or the components (A) to (D) and/or other optional components as required.
  • the composition may be: Liquid A: Component (B); Liquid B: Component (A), Component (C), and Component (D); Liquid A: Component (A), Component (B), and Component (D); Liquid B: Component (A), Component (C), and Component (D); Liquid A: Component (A), Component (E), and Component (H); Liquid B: Component (B), Component (C), and Component (D); Liquid A: Component (A), Component (F), and Component (H); or Liquid B: Component (B), Component (C), and Component (D).
  • Examples of cases in which components (A) to (C) or components (A) to (D) are contained in separate liquids include adhesives or sealants in which components (A) to (C) or components (A) to (D) are separated into two or more containers, specifically kits composed of multiple liquids containing any of components (A) to (C) or components (A) to (D).
  • semiconductor devices electronic components
  • semiconductor device refers to any device that can function by utilizing semiconductor properties, including electronic components, semiconductor circuits, modules incorporating these, electronic devices, etc.
  • 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.
  • C An acid generator (gallate-based acid generator) which is a salt formed from a gallate anion of formula (1) and a counter cation
  • C-1 an acid generator represented by the following formula: This acid generator was synthesized by the method described in JP 2022-080366 A. This acid generator can function as both a photoacid generator and a thermal acid generator.
  • C-2 Photoacid generator represented by the following formula: This photoacid generator was synthesized according to the method described in WO2018/020974.
  • C-3) A thermal acid generator represented by the following formula: This thermal acid generator was synthesized according to the method described in WO2018/020974.
  • C' Acid generator other than component (C) (borate-based acid generator) (C'-1): 4-isopropyl-4'-methyldiphenyliodonium tetrakis(pentafluorophenyl)borate (product name: BLUESIL (registered trademark) PI 2074, manufactured by ELKEM SILICONES)
  • D-1 Hydrophobic fumed silica (product name: CAB-O-SIL (registered trademark) TS720, manufactured by CABOT Corporation, average particle size: 12 nm)
  • D-2) Surface-treated silica filler (product name: SE5200SEE, average particle size 2 ⁇ m, manufactured by Admatechs Co., Ltd.)
  • the resin compositions of the examples and comparative examples were subjected to DSC measurement using a differential scanning calorimeter (DSC-50 manufactured by Shimadzu Corporation) by heating them from 25°C to 250°C at a heating rate of 10°C/min. From the obtained DSC curve, the calorific value (J/g) in the temperature range of 200°C to 250°C was determined.
  • the calorific value in the temperature range of 200°C to 250°C determined under the above conditions is preferably 10 J/g or less.
  • the photocuring conditions were as follows: using a single-wavelength UV LED light source (OmniCure (registered trademark) AC475, manufactured by Excelitas Technologies), at a height of 4 cm from the top surface of the test piece to the light source, wavelength: 365 nm ultraviolet light, irradiation intensity: 500 mW / cm 2 , and the cumulative light amount was continuously irradiated until it reached 2000 mJ / cm 2 (measured with an ultraviolet integrating actinometer UIT-250 and a photodetector UVD-S365 (manufactured by Ushio Inc.)).
  • the heat curing conditions were 80° C. and 60 minutes in a blower dryer.
  • the alumina chip on the FR4 plate of the test piece after reflow was poked from the side with a bond tester (manufactured by Dage, Series 4000) at 23°C, and the stress (N) at which the alumina chip peeled off was measured. This measurement was performed on 10 test pieces, and the average value of the obtained stress was calculated. This average value is shown in Table 1 as the post-reflow shear strength (unit: N/Chip) of the cured product. (4) The shear strength retention rate after reflow was calculated based on the following formula. The results are shown in Table 1. In this specification, the shear strength retention rate after reflow is preferably 50% or more.
  • Example 1 The resin compositions of Example 1 and Comparative Example 1 were applied to glass substrates at a thickness of 250 ⁇ 100 ⁇ m, and the samples were photocured and then thermally cured to prepare test specimens.
  • the photocuring conditions were a single-wavelength UV LED light source (OmniCure® AC475, manufactured by Excelitas Technologies) and were continuously irradiated at a height of 4 cm from the top surface of the test specimen to the light source, with ultraviolet light of 365 nm wavelength and irradiation intensity of 500 mW/cm 2 until the cumulative light dose reached 2000 mJ/cm 2 (measured using a UV integrating actinometer UIT-250 and a UVD-S365 photodetector (manufactured by Ushio Inc.)).
  • the thermal curing conditions were 80°C and 60 minutes in a blower dryer.
  • the resin composition of the present invention is extremely useful, and can be used, for example, as an adhesive or sealant for fixing, joining, or protecting semiconductor devices or electronic components or the components that make them up, or as a raw material for such adhesives or sealants.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Power Engineering (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Computer Hardware Design (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Condensed Matter Physics & Semiconductors (AREA)
  • Epoxy Resins (AREA)

Abstract

La présente invention aborde le problème de la fourniture : d'une composition de résine qui est susceptible au moins d'être photodurcie ou durcie à basse température (par exemple, 100 °C ou moins) et qui fournit un produit durci qui présente une excellente force adhésive et une excellente fiabilité de résistance à la chaleur ; d'un agent adhésif ou d'un matériau d'étanchéité qui la comprend ; de son produit durci ; et d'un dispositif à semi-conducteur et d'un composant électronique qui comprennent le produit durci.　L'invention concerne : une composition de résine contenant (A) un composé époxy, (B) un composé oxétane, et (C) un agent générateur d'acide qui est un sel d'un anion représenté par la formule (1) (Dans la formule, R1, R2, R3, et R4 représentent indépendamment un groupe alkyle ayant 1 à 18 atomes de carbone ou un groupe aryle ayant 6 à 14 atomes de carbone, à condition cependant qu'au moins l'un parmi R1, R2, R3, et R4 représente un groupe aryle ayant 6 à 14 atomes de carbone) et d'un contre-cation, et satisfaisant également au moins l'une des caractéristiques (a) et (b) suivantes ; un agent adhésif ou un matériau d'étanchéité la comprenant ; son produit durci ; et un dispositif à semi-conducteur et un composant électronique comprenant le produit durci. (a) (D) Une charge est en outre incluse. (b) La teneur en (A) le composé époxy est 100 à 1 300 parties en poids par rapport à 100 parties en poids de (B) le composé oxétane.
PCT/JP2025/008984 2024-03-25 2025-03-11 Composition de résine, agent adhésif, matériau d'étanchéité, produit durci, dispositif à semi-conducteur et composant électronique Pending WO2025204845A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2024048022 2024-03-25
JP2024-048022 2024-03-25

Publications (1)

Publication Number Publication Date
WO2025204845A1 true WO2025204845A1 (fr) 2025-10-02

Family

ID=97217939

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2025/008984 Pending WO2025204845A1 (fr) 2024-03-25 2025-03-11 Composition de résine, agent adhésif, matériau d'étanchéité, produit durci, dispositif à semi-conducteur et composant électronique

Country Status (1)

Country Link
WO (1) WO2025204845A1 (fr)

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005059002A1 (fr) * 2003-12-19 2005-06-30 Henkel Corporation Durcissement cationique d'une composition de resine epoxyde
JP2019183048A (ja) * 2018-04-13 2019-10-24 日本化薬株式会社 光熱併用硬化型樹脂組成物、接着剤及びその硬化物
JP2021147584A (ja) * 2020-03-23 2021-09-27 ヘンケルジャパン株式会社 デュアル硬化型接着剤組成物
JP2022080366A (ja) * 2020-11-18 2022-05-30 サンアプロ株式会社 光熱併用硬化型樹脂組成物、接着剤及びその硬化物
JP2023131845A (ja) * 2022-03-10 2023-09-22 協立化学産業株式会社 熱カチオン重合性樹脂組成物
WO2024142446A1 (fr) * 2022-12-27 2024-07-04 ナミックス株式会社 Composition de résine durcissable, adhésif, agent d'encapsulation, produit durci, dispositif à semi-conducteurs et dispositif électronique
WO2024142447A1 (fr) * 2022-12-27 2024-07-04 ナミックス株式会社 Composition de résine durcissable, adhésif, agent d'encapsulation, produit durci, dispositif à semi-conducteurs et dispositif électronique

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005059002A1 (fr) * 2003-12-19 2005-06-30 Henkel Corporation Durcissement cationique d'une composition de resine epoxyde
JP2019183048A (ja) * 2018-04-13 2019-10-24 日本化薬株式会社 光熱併用硬化型樹脂組成物、接着剤及びその硬化物
JP2021147584A (ja) * 2020-03-23 2021-09-27 ヘンケルジャパン株式会社 デュアル硬化型接着剤組成物
JP2022080366A (ja) * 2020-11-18 2022-05-30 サンアプロ株式会社 光熱併用硬化型樹脂組成物、接着剤及びその硬化物
JP2023131845A (ja) * 2022-03-10 2023-09-22 協立化学産業株式会社 熱カチオン重合性樹脂組成物
WO2024142446A1 (fr) * 2022-12-27 2024-07-04 ナミックス株式会社 Composition de résine durcissable, adhésif, agent d'encapsulation, produit durci, dispositif à semi-conducteurs et dispositif électronique
WO2024142447A1 (fr) * 2022-12-27 2024-07-04 ナミックス株式会社 Composition de résine durcissable, adhésif, agent d'encapsulation, produit durci, dispositif à semi-conducteurs et dispositif électronique

Similar Documents

Publication Publication Date Title
JP6036703B2 (ja) 硬化性樹脂組成物
JP6092165B2 (ja) 信頼性に優れた感光性樹脂組成物及びその製造方法
JP6171573B2 (ja) 感光性樹脂組成物および硬化膜
CN113302222B (zh) 可阳离子固化的组合物和使用该组合物接合、浇注和涂覆基材的方法
JP2010018797A (ja) 光学部品用硬化性組成物、光学部品用接着剤及び有機エレクトロルミネッセンス素子用封止剤
JP7614512B2 (ja) カチオン硬化性組成物、硬化物および接合体
WO2008032850A1 (fr) Composition photopolymérisable
WO2017082356A1 (fr) Composition de résine époxy contenant un groupe alcylène à longue chaîne
JP2017126074A (ja) 感光性樹脂組成物および硬化膜
JP6539488B2 (ja) 硬化物の製造方法、硬化物、硬化性組成物および接着剤
WO2018181846A1 (fr) Composition durcissable, procédé de production d'un produit durci, produit durci à base de celle-ci, et adhésif l'utilisant
JP6810681B2 (ja) モノマー混合物、及びそれを含む硬化性組成物
CN120265677A (zh) 固化性树脂组合物、粘结剂、密封材料、固化物、半导体装置以及电子器件
CN120225586A (zh) 固化性树脂组合物、粘结剂、密封材料、固化物、半导体装置以及电子器件
JP5256570B2 (ja) 封止用組成物
CN115151591B (zh) 组合物、固化物及固化物的制造方法
JP2005336349A (ja) カチオン重合型組成物
WO2025204845A1 (fr) Composition de résine, agent adhésif, matériau d'étanchéité, produit durci, dispositif à semi-conducteur et composant électronique
JP2007045986A (ja) 接着剤組成物およびそれを用いた接着フィルム、接着物の製造方法
JP7731213B2 (ja) 重合性組成物、光硬化性接着剤、硬化物の製造方法及び硬化物
JPWO2019003991A1 (ja) 有機ｅｌ素子の封止用のカチオン重合硬化型インクジェット用樹脂組成物
JP6331013B2 (ja) カチオン硬化性樹脂組成物
JP7667855B2 (ja) 表示素子用封止剤、その硬化物および表示装置
JP7634403B2 (ja) 基板積層体、および前記基板積層体の製造方法
WO2025205911A1 (fr) Composition de résine durcissable, composition adhésive, produit durci, dispositif à semi-conducteur, et composant électronique

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 25776449

Country of ref document: EP

Kind code of ref document: A1