[go: up one dir, main page]

WO2025115877A1 - Composition adhésive et stratifié - Google Patents

Composition adhésive et stratifié Download PDF

Info

Publication number
WO2025115877A1
WO2025115877A1 PCT/JP2024/041882 JP2024041882W WO2025115877A1 WO 2025115877 A1 WO2025115877 A1 WO 2025115877A1 JP 2024041882 W JP2024041882 W JP 2024041882W WO 2025115877 A1 WO2025115877 A1 WO 2025115877A1
Authority
WO
WIPO (PCT)
Prior art keywords
material layer
group
compound
adhesive composition
adhesive
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/JP2024/041882
Other languages
English (en)
Japanese (ja)
Inventor
拓生 四釜
佳保里 田村
靖剛 茅場
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.)
Mitsui Chemicals Inc
Original Assignee
Mitsui Chemicals Inc
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 Mitsui Chemicals Inc filed Critical Mitsui Chemicals Inc
Publication of WO2025115877A1 publication Critical patent/WO2025115877A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B7/00—Layered products characterised by the relation between layers; Layered products characterised by the relative orientation of features between layers, or by the relative values of a measurable parameter between layers, i.e. products comprising layers having different physical, chemical or physicochemical properties; Layered products characterised by the interconnection of layers
    • B32B7/04—Interconnection of layers
    • B32B7/12—Interconnection of layers using interposed adhesives or interposed materials with bonding properties
    • 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
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • 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
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/06—Non-macromolecular additives organic
    • 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
    • C09J179/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09J161/00 - C09J177/00
    • C09J179/02—Polyamines
    • 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
    • C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
    • C09J183/04—Polysiloxanes

Definitions

  • This disclosure relates to an adhesive composition and a laminate.
  • Patent Document 1 JP 2016-47895 A describes an adhesive that does not exhibit adhesive properties during stacking operations of semiconductor chips and the like, but softens when heated to exhibit adhesive properties, and then quickly hardens.
  • Patent document 1 JP 2016-47895 A
  • Patent Document 1 a laminate is produced by bonding a glass plate and a silicon plate using an adhesive, but there is no description of an example in which an adhesive is used to bond an inorganic material and an organic material. Furthermore, in recent years, there has been a trend toward even higher integration of semiconductor chips. In addition to substrates made of inorganic materials, the use of substrates made of organic materials such as thermosetting resins (hereinafter also referred to as organic substrates) has been considered. When an inorganic substrate is used, in order to improve the wettability of the adhesive, the substrate may be surface-treated with an organic solvent or a so-called leveling agent may be added to the adhesive composition.
  • organic substrates such as thermosetting resins
  • An object of one embodiment of the present disclosure is to provide an adhesive composition that is capable of forming a uniform coating film even when an organic substrate is used, and a laminate using this adhesive composition.
  • An adhesive composition comprising: a compound (A) having a cationic functional group containing at least one selected from a primary nitrogen atom and a secondary nitrogen atom and a Si—O bond; a crosslinking agent (B) having three or more —C( ⁇ O)OX groups in the molecule, X representing a hydrogen atom or an alkyl group having from 1 to 6 carbon atoms, and of the three or more —C( ⁇ O)OX groups, one to six are —C( ⁇ O)OH groups, and having a weight average molecular weight of 200 or more and 600 or less; and an additive (D) having a structure represented by the following formula (a) and a structure represented by the following formula (b):
  • ⁇ 2> The adhesive composition according to ⁇ 1>, wherein a content of the additive (D) is 0.1 parts by mass or more and 7 parts by mass or less with respect to 100 parts by mass of a total content of the compound (A) and the crosslinking agent (B).
  • a content of the additive (D) is 0.1 parts by mass or more and 7 parts by mass or less with respect to 100 parts by mass of a total content of the compound (A) and the crosslinking agent (B).
  • ⁇ 3> The adhesive composition according to ⁇ 1> or ⁇ 2>, further comprising a polar solvent (C).
  • polar solvent (C) contains at least water.
  • ⁇ 5> The adhesive composition according to ⁇ 3> or ⁇ 4>, in which a content of the additive (D) is 0.01 parts by mass or more and 0.8 parts by mass or less, relative to 100 parts by mass of a total content of the compound (A), the crosslinking agent (B), and the polar solvent (C).
  • a content of the additive (D) is 0.01 parts by mass or more and 0.8 parts by mass or less, relative to 100 parts by mass of a total content of the compound (A), the crosslinking agent (B), and the polar solvent (C).
  • a laminate comprising an inorganic material layer, an organic material layer, and an adhesive layer disposed between the inorganic material layer and the organic material layer and bonding the inorganic material layer to the organic material layer, the adhesive layer comprising the adhesive composition according to claim 1 or 2.
  • a laminate comprising an inorganic material layer, an organic material layer, and an adhesive layer disposed between the inorganic material layer and the organic material layer and bonding the inorganic material layer and the organic material layer, the adhesive layer comprising: a reaction product of a compound (A) having a cationic functional group containing at least one selected from a primary nitrogen atom and a secondary nitrogen atom and a Si—O bond, and a crosslinking agent (B) having three or more —C( ⁇ O)OX groups (X is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms) in the molecule, wherein one to six of the three or more —C( ⁇ O)OX groups are —C( ⁇ O)OH groups, and having a weight average molecular weight of 200 to 600, and an additive (D) having a structure represented by the following formula (a) and a structure represented by the following formula (b):
  • R 1 and R 2 each independently represent a hydrogen atom or an organic group having 1 to 10 carbon atoms.
  • n represents an integer of 1 to 40
  • m represents an integer of 1 to 30
  • x represents an integer of 1 to 300
  • y represents an integer of 1 to 100.
  • an adhesive composition capable of forming a uniform coating film even when an organic substrate is used, and a laminate using this adhesive composition are provided.
  • a numerical range expressed using “to” means a range that includes the numerical values before and after "to” as the lower and upper limits.
  • the upper or lower limit value described in one numerical range may be replaced with the upper or lower limit value of another numerical range described in stages.
  • the upper or lower limit value of the numerical range may be replaced with a value shown in the examples.
  • the term "laminate” refers to a structure in which an inorganic material layer, an adhesive layer, and an organic material layer are arranged in this order, and the inorganic material layer and the organic material layer are bonded via the adhesive layer.
  • the adhesive composition of the present disclosure includes a compound (A) having a cationic functional group containing at least one selected from a primary nitrogen atom and a secondary nitrogen atom and a Si—O bond, a crosslinking agent (B) having three or more -C( ⁇ O)OX groups in the molecule, X representing a hydrogen atom or an alkyl group having from 1 to 6 carbon atoms, and of the three or more -C( ⁇ O)OX groups, one to six are -C( ⁇ O)OH groups, and having a weight average molecular weight of 200 or more and 600 or less, and an additive (D) having a structure represented by the following formula (a) and a structure represented by the following formula (b):
  • the adhesive composition contains the compound (A) and the crosslinking agent (B), and thus the adhesive property to an inorganic substrate and the adhesive strength after heating are improved. Furthermore, when the adhesive composition contains the additive (D), the affinity of the adhesive composition to the resin substrate is improved.
  • the mechanism by which the affinity for the resin substrate is improved is not clear, but is presumed to be as follows.
  • additive (D) containing a siloxane bond represented by formula (a) as a partial structure improves adhesion to inorganic materials and organic materials, and further, containing an ether bond represented by formula (b) causes the ether bond to be unevenly distributed on the organic substrate side in the adhesive composition, improving affinity with organic substrates; for example, even when the adhesive composition contains a polar solvent, repelling of the adhesive composition is suppressed when applied to an organic substrate, enabling the formation of a uniform coating film.
  • the partial structure represented by formula (b) is present in the side chain of additive (D) to improve the mobility of the ether bond, to further improve the affinity to the resin substrate, and to provide superior coatability.
  • R 01 and R 02 each independently represent a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, or a group represented by the following formula (a-2).
  • R 1 and R 2 each independently represent a hydrogen atom or an organic group having 1 to 10 carbon atoms.
  • examples of the organic group include an aliphatic hydrocarbon group having 1 to 10 carbon atoms and an aromatic hydrocarbon group having 1 to 10 carbon atoms.
  • examples of the aliphatic hydrocarbon group include an alkyl group having 1 to 5 carbon atoms, such as a methyl group and an ethyl group, and examples of the aliphatic hydrocarbon group include a phenyl group.
  • x represents an integer of 1 to 300, preferably 1 to 280, more preferably 1 to 100, and even more preferably 1 to 50.
  • y represents an integer of 1 to 100, preferably 1 to 90, more preferably 1 to 50, and even more preferably 1 to 20.
  • R 01 and R 02 represent an organic group having 1 to 10 carbon atoms
  • examples of the organic group include an aliphatic hydrocarbon group having 1 to 10 carbon atoms and an aromatic hydrocarbon group having 1 to 10 carbon atoms.
  • examples of the aliphatic hydrocarbon group include an alkyl group having 1 to 5 carbon atoms, such as a methyl group and an ethyl group, and examples of the aliphatic hydrocarbon group include a phenyl group.
  • the additive (D) may be a compound having a structure represented by the following formula (c): According to formula (c), by having a siloxane bond represented by the above formula (a) in the main chain and an ether bond represented by formula (b) in the side chain, the adhesive composition can be more easily formed into a uniform coating film on an organic substrate.
  • R 1 and R 2 each independently represent a hydrogen atom or an organic group having 1 to 10 carbon atoms.
  • examples of the organic group include an aliphatic hydrocarbon group having 1 to 10 carbon atoms and an aromatic hydrocarbon group having 1 to 10 carbon atoms. More specific examples of the hydrocarbon group include alkyl groups such as a methyl group, an ethyl group, and a propyl group, and a phenyl group. From the viewpoint of improving affinity with the organic substrate, it is particularly preferred that in formula (c), R 1 is a hydrogen atom or a methyl group, and R 2 is a methyl group or an ethyl group.
  • n represents an integer of 1 to 40, preferably 1 to 38, and more preferably 1 to 10.
  • m represents an integer of 1 to 30, preferably 1 to 29, and more preferably 1 to 10.
  • x represents an integer of 1 to 300, preferably 1 to 280, more preferably 1 to 100, and even more preferably 1 to 50.
  • y represents an integer of 1 to 100, preferably 1 to 90, more preferably 1 to 50, and even more preferably 1 to 20.
  • the weight average molecular weight of additive (D) can be in the range of 500 to 5000, preferably 700 to 3000, more preferably 800 to 2000, and even more preferably 800 to 1000.
  • the weight average molecular weight of additive (D) is 500 or more, the affinity to the resin substrate is good, and when it is 5000 or less, the solubility during preparation of the adhesive composition and the uniformity in the solution are good.
  • the weight average molecular weight refers to the weight average molecular weight in terms of polyethylene glycol, measured by Gel Permeation Chromatography (GPC) for a substance other than the monomer. Specifically, the weight average molecular weight is analyzed using tetrahydrofuran as a developing solvent, a Shodex DET RI-101 analyzer, and an analytical column (2x PLgel 5 ⁇ MIXED-D, 7.5 x 300 mm/40°C, manufactured by Agilent Technologies) at a flow rate of 1.0 mL/min to detect the refractive index, and polyethylene glycol/polyethylene oxide as a standard.
  • GPC Gel Permeation Chromatography
  • R 1 represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms
  • R 2 represents an organic group having 1 to 10 carbon atoms.
  • Additive (D) may be a commercially available product.
  • Examples of commercially available additive (D) that may be used in the adhesive composition of the present disclosure include silicone surface conditioners from BYK Japan Co., Ltd., such as BYK-333, BYK-307, BYK-302, BYK-325, BYK-331, BYK-342, BYK-345, BYK-346, BYK-347, BYK-348, BYK-349, BYK-378, BYK-3455, and BYK-3456.
  • the adhesive composition of the present disclosure contains at least a compound (A), a crosslinking agent (B), and an additive (D). Details of the compound (A) and the crosslinking agent (B) will be described later.
  • the content of the additive (D) is preferably 0.1 parts by mass or more and 7 parts by mass or less, relative to 100 parts by mass of the total content of the compound (A) and the crosslinking agent (B).
  • the adhesive composition has better ability to form a uniform coating film on an organic substrate.
  • the content of the additive (D) is preferably 0.1 parts by mass or more and 7 parts by mass or less, more preferably 0.1 parts by mass or more and 5 parts by mass or less, and even more preferably 1 part by mass or more and 3 parts by mass or less, relative to 100 parts by mass of the total content of the compound (A) and the crosslinking agent (B) [hereinafter also referred to as (A+B)].
  • the adhesive composition of the present disclosure may further contain a polar solvent (C).
  • a polar solvent (C) By including the polar solvent (C) in the adhesive composition of the present disclosure, the environmental impact is reduced and the composition can be more easily prepared.
  • the polar solvent (C) preferably contains at least water.
  • a polar solvent (C) such as water
  • the affinity to an organic substrate decreases, and repelling is likely to occur when the composition is applied to a resin substrate, but when the adhesive composition contains the additive (D), the occurrence of repelling is suppressed, and the uniform application to a resin substrate is improved. Therefore, it is considered that the adhesive composition of the present disclosure has a remarkable effect in an embodiment containing a polar solvent (C) as a solvent.
  • the polar solvent (C) will be described in detail below.
  • the adhesive composition of the present disclosure further contains a polar solvent (C) in addition to the compound (A), the crosslinking agent (B), and the additive (D)
  • the content of the additive (D) is preferably 0.01 parts by mass or more and 0.8 parts by mass or less per 100 parts by mass of the total content of the compound (A), the crosslinking agent (B), and the polar solvent (C).
  • the adhesive composition exhibits better formability of a uniform coating film on a resin substrate, even when the adhesive composition contains a polar solvent (C).
  • the amount is more preferably 0.1 parts by mass or more and 0.6 parts by mass or less, and even more preferably 0.1 parts by mass or more and 0.5 parts by mass or less, relative to 100 parts by mass of the total content of the compound (A), the crosslinking agent (B), and the polar solvent (C) [hereinafter, also referred to as (A+B+C)].
  • the adhesive composition of the present disclosure may contain only one type of additive (D), or may contain two or more types.
  • the content of the additive (D) relative to the total mass of the adhesive composition is preferably 0.1 mass % to 0.6 mass %, and more preferably 0.1 mass % to 0.5 mass %.
  • inorganic material layer inorganic substrate
  • organic material layer organic substrate
  • the adhesive composition of the present disclosure is disposed between an inorganic material layer and an organic material layer and is used to bond the inorganic material layer and the organic material layer.
  • the type of inorganic material constituting the inorganic material layer to which the adhesive composition of the present disclosure is applied are no particular limitations.
  • inorganic materials include semiconductors such as Si, InP, GaN, GaAs, InGaAs, InGaAlAs, SiGe, and SiC; oxides, carbides, and nitrides such as boron silicate glass (Pyrex (registered trademark )), quartz glass ( SiO2 ), sapphire ( Al2O3 ) , ZrO2 , Si3N4 , SiCN, AlN, and MgAl2O4 ; piezoelectrics or dielectrics such as BaTiO3 , LiNbO3 , SrTiO3 , and LiTaO3 ; diamond; metals such as Al, Ti, Fe, Cu, Ag, Au, Pt, Pd, Ta, and Nb; and carbon.
  • Si, SiO 2 , SiC and SiCN are preferred.
  • the inorganic material layer may be a self-supporting object, or may be formed in a layer on the surface of another object.
  • the type of the other object is not particularly limited, and may be an inorganic material or an organic material.
  • the inorganic material layer may have an electrode on the surface facing the organic material layer.
  • Organic material layer There are no particular limitations on the type of organic material constituting the organic substrate (organic material layer) to which the adhesive composition of the present disclosure is applied. Specific examples of the organic material include epoxy resin, phenol resin, silicone resin, polyimide, benzocyclobutene resin, and polybenzoxazole.
  • the adhesive composition of the present disclosure contains at least the following compound (A) and crosslinking agent (B) in addition to the additive (D), and may further contain a polar solvent (C) as desired.
  • Compound (A) A compound having a cationic functional group containing at least one of a primary nitrogen atom and a secondary nitrogen atom and an Si—O bond.
  • -Compound (A)- Compound (A) has a cationic functional group containing at least one of a primary nitrogen atom and a secondary nitrogen atom.
  • the cationic functional group is not particularly limited as long as it can bear a positive charge and contains at least one of a primary nitrogen atom and a secondary nitrogen atom.
  • the compound (A) may contain a tertiary nitrogen atom in addition to the primary and secondary nitrogen atoms.
  • the compound (A) preferably has two or three Si—O bonds.
  • a "primary nitrogen atom” refers to a nitrogen atom that is bonded to only two hydrogen atoms and one atom other than a hydrogen atom (e.g., a nitrogen atom contained in a primary amino group ( -NH2 group)), or a nitrogen atom that is bonded to only three hydrogen atoms and one atom other than a hydrogen atom (cation).
  • second nitrogen atom refers to a nitrogen atom bonded to only one hydrogen atom and two atoms other than hydrogen atoms (i.e., a nitrogen atom contained in a functional group represented by the following formula (a1)), or a nitrogen atom (cation) bonded to only two hydrogen atoms and two atoms other than hydrogen atoms.
  • tertiary nitrogen atom refers to a nitrogen atom bonded to only three atoms other than hydrogen atoms (i.e., a nitrogen atom that is a functional group represented by the following formula (b1)), or a nitrogen atom (cation) bonded to one hydrogen atom and only three atoms other than hydrogen atoms.
  • the functional group represented by formula (a1) may be a functional group constituting a part of a secondary amino group (-NHR a group; here, R a represents an alkyl group), or may be a divalent linking group contained in the skeleton of a polymer.
  • the functional group represented by formula (b1) may be a functional group constituting a part of a tertiary amino group (-NR b R c group; here, R b and R c each independently represent an alkyl group), or may be a trivalent linking group contained in the skeleton of a polymer.
  • the weight average molecular weight of compound (A) is preferably 130 or more and 10,000 or less, more preferably 130 or more and 5,000 or less, and even more preferably 130 or more and 2,000 or less.
  • the weight average molecular weight of a compound refers to the weight average molecular weight in terms of polyethylene glycol measured by GPC (Gel Permeation Chromatography) method. Specifically, the weight-average molecular weight of the compound is calculated using an aqueous solution of sodium nitrate having a concentration of 0.1 mol/L as a developing solvent, detecting the refractive index at a flow rate of 1.0 mL/min using an analytical device Shodex DET RI-101 and two types of analytical columns (TSKgel G6000PWXL-CP and TSKgel G3000PWXL-CP, both manufactured by Tosoh), and using polyethylene glycol/polyethylene oxide as standards with analytical software (Empower3, manufactured by Waters).
  • GPC Gel Permeation Chromatography
  • the compound (A) may further have an anionic functional group, a nonionic functional group, or the like, as necessary.
  • the nonionic functional group may be a hydrogen bond accepting group or a hydrogen bond donating group.
  • Examples of the nonionic functional group include a hydroxyl group, a carbonyl group, and an ether group (-O-).
  • the anionic functional group is not particularly limited as long as it is a functional group that can bear a negative charge.
  • Examples of the anionic functional group include a carboxylic acid group, a sulfonic acid group, and a sulfate group.
  • the compound (A) may be a compound having a Si—O bond and an amino group.
  • examples of compounds having an Si--O bond and an amino group include siloxane diamine, a silane coupling agent having an amino group, and a siloxane polymer.
  • An example of the silane coupling agent having an amino group is a compound represented by the following formula (A-3).
  • R 1 represents an alkyl group having 1 to 4 carbon atoms which may be substituted.
  • R 2 and R 3 each independently represent an alkylene group having 1 to 12 carbon atoms, an ether group, or a carbonyl group which may be substituted (the skeleton may contain a carbonyl group, an ether group, etc.).
  • R 4 and R 5 each independently represent an alkylene group having 1 to 4 carbon atoms which may be substituted or a single bond.
  • Ar represents a divalent or trivalent aromatic ring.
  • X 1 represents hydrogen or an alkyl group having 1 to 5 carbon atoms which may be substituted.
  • X 2 represents hydrogen, a cycloalkyl group, a heterocyclic group, an aryl group, or an alkyl group having 1 to 5 carbon atoms which may be substituted (the skeleton may contain a carbonyl group, an ether group, etc.).
  • a plurality of R 1 , R 2 , R 3 , R 4 , R 5 , and X 1 may be the same or different.
  • Substituents of the alkyl and alkylene groups in R1 , R2 , R3 , R4 , R5 , X1 and X2 each independently include an amino group, a hydroxy group, an alkoxy group, a cyano group, a carboxylic acid group, a sulfonic acid group and halogens.
  • Examples of the divalent or trivalent aromatic ring in Ar include a divalent or trivalent benzene ring.
  • Examples of the aryl group in X2 include a phenyl group, a methylbenzyl group, and a vinylbenzyl group.
  • silane coupling agents represented by formula (A-3) include, for example, N-(2-aminoethyl)-3-aminopropylmethyldiethoxysilane, N-(2-aminoethyl)-3-aminopropyltriethoxysilane, N-(2-aminoethyl)-3-aminoisobutyldimethylmethoxysilane, N-(2-aminoethyl)-3-aminoisobutylmethyldimethoxysilane, N-(2-aminoethyl)-11-aminoundecyltrimethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, N-phenyl-3-aminopropyltrimethoxysilane, (aminoethylaminoethyl)phenyltriethoxysilane, methylbenzylaminoethyla
  • silane coupling agents having an amino group other than that represented by formula (A-3) include N,N-bis[3-(trimethoxysilyl)propyl]ethylenediamine, N,N'-bis[3-(trimethoxysilyl)propyl]ethylenediamine, bis[(3-triethoxysilyl)propyl]amine, piperazinylpropylmethyldimethoxysilane, bis[3-(triethoxysilyl)propyl]urea, bis(methyldiethoxysilylpropyl)amine,
  • the silyl group include 2,2-dimethoxy-1,6-diaza-2-silacyclooctane, 3,5-diamino-N-(4-(methoxydimethylsilyl)phenyl)benzamide, 3,5-diamino-N-(4-(triethoxysilyl)phenyl)benzamide, 5-(ethoxydimethylsilyl)benzene
  • silane coupling agents having an amino group may be used alone or in combination of two or more.
  • a silane coupling agent having an amino group may also be used in combination with a silane coupling agent not having an amino group.
  • a silane coupling agent having a mercapto group may be used to improve adhesion to metals.
  • Compound (A) may be a polymer (siloxane polymer) formed from the above-mentioned silane coupling agent via a siloxane bond (Si-O-Si).
  • siloxane polymer formed from the above-mentioned silane coupling agent via a siloxane bond (Si-O-Si).
  • a polymer having a linear siloxane structure, a polymer having a branched siloxane structure, a polymer having a cyclic siloxane structure, a polymer having a cage siloxane structure, etc. can be obtained from the hydrolyzate of 3-aminopropyltrimethoxysilane.
  • the cage siloxane structure is represented, for example, by the following formula (A-1).
  • siloxane diamines examples include compounds represented by the following formula (A-2).
  • i is an integer from 0 to 4
  • j is an integer from 1 to 3
  • Me is a methyl group.
  • compound (A) has a cationic functional group containing at least one of a primary nitrogen atom and a secondary nitrogen atom, it can strongly adhere to the surface of the inorganic material layer and/or the organic material layer by electrostatic interaction with functional groups such as hydroxyl groups, epoxy groups, carboxy groups, amino groups, and mercapto groups that may be present on the surface of the inorganic material layer and/or the organic material layer, or by forming a covalent bond with the functional groups.
  • functional groups such as hydroxyl groups, epoxy groups, carboxy groups, amino groups, and mercapto groups that may be present on the surface of the inorganic material layer and/or the organic material layer, or by forming a covalent bond with the functional groups.
  • Compound (A) has a cationic functional group containing at least one of a primary nitrogen atom and a secondary nitrogen atom, and therefore is easily soluble in polar solvent (C).
  • polar solvent (C) By using compound (A) that is easily soluble in polar solvent (C), when the surface of the inorganic material layer or organic material layer is hydrophilic, the affinity with these surfaces is increased. As a result, a smooth adhesive layer can be formed.
  • the molar ratio (non-crosslinkable group/Si element) of the Si element in the molecule to the non-crosslinkable group such as a methyl group bonded to the Si element in the compound (A) is less than 2 (satisfying the relationship: non-crosslinkable group/Si element ⁇ 2).
  • compound (A) contains a primary nitrogen atom
  • the proportion of primary nitrogen atoms in the total nitrogen atoms in compound (A) is preferably 20 mol% or more, more preferably 25 mol% or more, and even more preferably 30 mol% or more.
  • Compound (A) may also have a cationic functional group that contains a primary nitrogen atom and does not contain any nitrogen atoms other than the primary nitrogen atom (e.g., secondary nitrogen atom, tertiary nitrogen atom).
  • the ratio of secondary nitrogen atoms to the total nitrogen atoms in compound (A) is preferably 5 mol% or more and 50 mol% or less, and more preferably 10 mol% or more and 45 mol% or less.
  • Compound (A) may contain a tertiary nitrogen atom in addition to a primary nitrogen atom and a secondary nitrogen atom.
  • the ratio of tertiary nitrogen atoms to the total nitrogen atoms in compound (A) is preferably 20 mol % or more and 50 mol % or less, and more preferably 25 mol % or more and 45 mol % or less.
  • the content of compound (A) in the composition is not particularly limited, but can be, for example, 0.001% by mass or more and 20% by mass or less, preferably 0.01% by mass or more and 20% by mass or less, and more preferably 0.04% by mass or more and 20% by mass or less, relative to the entire composition.
  • the weight average molecular weight of the compound (B) is not particularly limited.
  • the weight average molecular weight of the compound (B) may be 200 or more and 600 or less, 200 or more and 500 or less, 200 or more and 450 or less, or 200 or more and 400 or less.
  • the weight average molecular weight of the compound (B) is within the above range, the solubility in the composition is improved.
  • the crosslinking agent (B) has a ring structure in the molecule.
  • the ring structure include an alicyclic structure and an aromatic ring structure.
  • the crosslinking agent (B) may have multiple ring structures in the molecule, and the multiple ring structures may be the same or different.
  • the heat resistance of the adhesive layer is improved.
  • Examples of the alicyclic structure include alicyclic structures having 3 to 8 carbon atoms, preferably 4 to 6 carbon atoms, and the ring structure may be saturated or unsaturated. More specifically, examples of the alicyclic structure include saturated alicyclic structures such as a cyclopropane ring, a cyclobutane ring, a cyclopentane ring, a cyclohexane ring, a cycloheptane ring, and a cyclooctane ring; and unsaturated alicyclic structures such as a cyclopropene ring, a cyclobutene ring, a cyclopentene ring, a cyclohexene ring, a cycloheptene ring, and a cyclooctene ring.
  • saturated alicyclic structures such as a cyclopropane ring, a cyclobutane ring, a cyclopen
  • the aromatic ring structure is not particularly limited as long as it is a ring structure that exhibits aromaticity, and examples thereof include benzene-based aromatic rings such as a benzene ring, a naphthalene ring, an anthracene ring, and a perylene ring, aromatic heterocycles such as a pyridine ring and a thiophene ring, and non-benzene-based aromatic rings such as an indene ring and an azulene ring.
  • benzene-based aromatic rings such as a benzene ring, a naphthalene ring, an anthracene ring, and a perylene ring
  • aromatic heterocycles such as a pyridine ring and a thiophene ring
  • non-benzene-based aromatic rings such as an indene ring and an azulene ring.
  • the ring structure that the crosslinking agent (B) has in its molecule is preferably at least one selected from the group consisting of a cyclobutane ring, a cyclopentane ring, a cyclohexane ring, a benzene ring, and a naphthalene ring, and from the viewpoint of further increasing the heat resistance of the adhesive layer, at least one of a benzene ring and a naphthalene ring is more preferable.
  • the crosslinking agent (B) may have multiple ring structures in the molecule, and when the ring structure is benzene, it may have a biphenyl structure, a benzophenone structure, a diphenyl ether structure, etc.
  • the crosslinking agent (B) may have a fluorine atom in the molecule. For example, it may have 1 to 6 fluorine atoms in the molecule, or 3 to 6 fluorine atoms in the molecule.
  • the compound (B) may have a fluoroalkyl group in the molecule, specifically, it may have a trifluoroalkyl group or a hexafluoroisopropyl group. If the crosslinking agent (B) has a fluorine atom in the molecule, the water absorption of the adhesive layer decreases.
  • crosslinking agent (B) examples include carboxylic acid compounds such as alicyclic carboxylic acids, benzene carboxylic acids, naphthalene carboxylic acids, diphthalic acids, and fluorinated aromatic carboxylic acids, and carboxylic acid ester compounds such as alicyclic carboxylic acid esters, benzene carboxylic acid esters, naphthalene carboxylic acid esters, diphthalic acid esters, and fluorinated aromatic carboxylic acid esters.
  • carboxylic acid compounds such as alicyclic carboxylic acids, benzene carboxylic acids, naphthalene carboxylic acids, diphthalic acids, and fluorinated aromatic carboxylic acid esters
  • carboxylic acid ester compounds such as alicyclic carboxylic acid esters, benzene carboxylic acid esters, naphthalene carboxylic acid esters, diphthalic acid esters, and fluorinated aromatic carboxylic acid esters.
  • the crosslinking agent (B) contained in the adhesive is a carboxylate compound, aggregation due to association between the compound (A) and the crosslinking agent (B) in the composition is suppressed, and aggregates and pits in the cured product are reduced, resulting in an adhesive layer with higher smoothness and making it easier to adjust the thickness of the adhesive layer.
  • X is preferably a methyl group, an ethyl group, a propyl group, or a butyl group
  • X is preferably an ethyl group or a propyl group.
  • carboxylic acid compound examples include, but are not limited to, alicyclic carboxylic acids such as 1,2,3,4-cyclobutanetetracarboxylic acid, 1,2,3,4-cyclopentanetetracarboxylic acid, 1,3,5-cyclohexanetricarboxylic acid, 1,2,4-cyclohexanetricarboxylic acid, 1,2,4,5-cyclohexanetetracarboxylic acid, and 1,2,3,4,5,6-cyclohexanehexacarboxylic acid; benzene carboxylic acids such as 1,2,4-benzenetricarboxylic acid, 1,3,5-benzenetricarboxylic acid, pyromellitic acid, benzenepentacarboxylic acid, and mellitic acid; naphthalene carboxylic acids such as 1,4,5,8-naphthalenetetracarboxylic acid and 2,3,6,7-naphthalenetetracarboxylic acid; 3,3'
  • carboxylic acid ester compound examples include compounds in which at least one carboxy group in the specific examples of the carboxylic acid compound described above has been replaced with an ester group.
  • carboxylic acid ester compound examples include half-esterified compounds represented by the following formulas (B-1) to (B-6).
  • R is an alkyl group having 1 to 6 carbon atoms, and among these, a methyl group, an ethyl group, a propyl group, or a butyl group is preferable, and an ethyl group or a propyl group is more preferable.
  • a half-esterified compound can be produced, for example, by mixing a carboxylic acid anhydride, which is the anhydride of the aforementioned carboxylic acid compound, with an alcohol solvent and opening the ring of the carboxylic acid anhydride.
  • the content of the crosslinking agent (B) in the composition is, for example, preferably an amount such that the ratio (COOH/N) of the number of carboxy groups in the crosslinking agent (B) to the total number of nitrogen atoms in the compound (A) is 0.1 or more and 3.0 or less, more preferably an amount such that the ratio is 0.3 or more and 2.5 or less, and even more preferably an amount such that the ratio is 0.4 or more and 2.2 or less.
  • a crosslinked structure such as an amide bond or an imide bond is sufficiently formed between the compound (A) and the crosslinking agent (B) after heat treatment, and an adhesive layer with excellent heat resistance and insulating properties is formed.
  • the ratio (COOH/N) of the number of carboxy groups in crosslinking agent (B) to the total number of all nitrogen atoms contained therein and in compound (A) is preferably 0.1 or more and 3.0 or less.
  • the content ratio (feed ratio) of the compound (A) to the crosslinking agent (B) in the composition is preferably a molar ratio of compound (A):crosslinking agent (B) of 2:0.9 to 2:1.1, and more preferably a molar ratio of 2:1. It is believed that the compound (A) and the crosslinking agent (B) in the composition exist as a mixture in a state in which the amino group of the compound (A) and the carboxy group of the crosslinking agent (B) form a salt in the polar solvent (C).
  • a cured product obtained by heating a composition containing compound (A) and crosslinking agent (B) is considered to contain, as a structural unit, a reaction product between compound (A) and crosslinking agent (B) as exemplified below.
  • the adhesive composition of the present disclosure may further contain a polar solvent (C).
  • a polar solvent refers to a solvent having a relative dielectric constant of 5 or greater at room temperature (25° C.).
  • the polar solvent (C) may be used alone or in combination of two or more kinds.
  • polar solvent (C) examples include protic solvents such as water and heavy water; alcohols such as methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-butanol, isobutyl alcohol, isopentyl alcohol, cyclohexanol, ethylene glycol, propylene glycol, 2-methoxyethanol, 2-ethoxyethanol, benzyl alcohol, diethylene glycol, triethylene glycol, and glycerin; ethers such as tetrahydrofuran and dimethoxyethane; aldehydes and ketones such as furfural, acetone, ethyl methyl ketone, and cyclohexanone; acid derivatives such as ethyl acetate, butyl acetate, ethylene carbonate, propylene carbonate, formaldehyde, N-methylformamide, N,N-dimethylformamide, N-methylacetamide, N,N-dimethylace,
  • the content of the polar solvent (C) in the composition is not particularly limited, and may be, for example, 1.0% by mass or more and 99.99896% by mass or less, or 40% by mass or more and 99.99896% by mass or less, relative to the entire composition.
  • the boiling point of the polar solvent (C) is preferably 150°C or lower, and more preferably 120°C or lower.
  • the composition may contain known additives (also referred to as other additives) other than the additive (D) described above.
  • additives include an acid having a carboxy group and a weight average molecular weight of 46 to 195, a base having a nitrogen atom and no ring structure and a weight average molecular weight of 17 to 120, and a solvent other than the polar solvent (C).
  • the composition may contain a solvent other than the polar solvent (C).
  • a solvent other than the polar solvent include normal hexane.
  • the composition may contain benzotriazole or a derivative thereof, for example to inhibit copper corrosion.
  • the pH of the composition is not particularly limited, but is preferably from 2.0 to 12.0. When the pH of the composition is 2.0 or more and 12.0 or less, damage to the substrate caused by the composition is suppressed.
  • the composition preferably contains 10 ppb by mass or less of sodium and potassium on an elemental basis, respectively. If the content of sodium or potassium is 10 ppb by mass or less on an elemental basis, the occurrence of problems in the electrical characteristics of the semiconductor device, such as malfunction of a transistor, can be suppressed.
  • the total content of the compound (A) and the crosslinking agent (B) is preferably 50% by mass or more, more preferably 70% by mass or more, and even more preferably 80% by mass or more of the total mass of the nonvolatile content in the composition.
  • nonvolatile content refers to components other than components (solvents, etc.) that are removed when the composition becomes a cured product.
  • the method for producing the composition is not particularly limited, and can be carried out by a known method.
  • the composition can be produced by a method including the following steps (a), (b) and (c).
  • the composition can be cured by heating to form an adhesive layer.
  • the heating temperature for curing the composition is preferably 150° C. to 450° C., more preferably 150° C. to 400° C., and even more preferably 180° C. to 400° C.
  • the above temperature refers to the temperature of the surface of the composition.
  • the heating time of the composition is not particularly limited and may be, for example, 3 hours or less or 1 hour or less.
  • the lower limit of the heating time is not particularly limited and may be, for example, 5 minutes or more.
  • the composition may be irradiated with ultraviolet (UV) rays.
  • Whether the composition is cured after heating can be confirmed, for example, by measuring the peak intensity of specific bonds and structures by Fourier transform infrared spectroscopy (FT-IR).
  • specific bonds and structures include bonds and structures generated by a crosslinking reaction.
  • FT-IR Fourier transform infrared spectroscopy
  • the composition is cured.
  • the presence or absence of an amide bond can be confirmed by the presence or absence of vibration peaks at about 1650 cm -1 and about 1520 cm -1 .
  • the presence or absence of an imide bond can be confirmed by the presence or absence of vibration peaks at about 1770 cm -1 and about 1720 cm -1 .
  • a first embodiment of the laminate of the present disclosure has an inorganic material layer, an organic material layer, and an adhesive layer disposed between the inorganic material layer and the organic material layer and bonding the inorganic material layer to the organic material layer, the adhesive layer containing the adhesive composition of the present disclosure described above.
  • the laminate of the present disclosure has an inorganic material layer and an organic material layer bonded together via an adhesive layer formed from the adhesive composition of the present disclosure, and the adhesive layer exhibits excellent adhesion to both the inorganic material layer and the organic material layer due to the function of the adhesive composition.
  • A a cationic functional group containing at least one selected from a primary nitrogen
  • the ratio (X/Y) of the die shear strength X (MPa) between the inorganic material layer and the organic material layer to the thickness Y ( ⁇ m) of the adhesive layer is preferably 1.2 or more, more preferably 1.5 or more, and even more preferably 2.0 or more.
  • the upper limit of the ratio (X/Y) of the die shear strength X (MPa) between the inorganic material layer and the organic material layer to the thickness Y ( ⁇ m) of the adhesive layer is not particularly limited, and may be, for example, 10 or less, 8 or less, or 6 or less.
  • the die shear strength between the inorganic material layer and the organic material layer is measured by the method described in the Examples.
  • the thickness Y of the adhesive layer is preferably 0.2 ⁇ m or more, more preferably 0.5 ⁇ m or more, and further preferably 1.0 ⁇ m or more. From the viewpoint of ensuring sufficient heat dissipation, the thickness Y of the adhesive layer is preferably 10 ⁇ m or less, more preferably 7.5 ⁇ m or less, further preferably 5.0 ⁇ m or less, and even more preferably 3.0 ⁇ m or less.
  • the thickness of the adhesive layer is measured by the method described in the Examples.
  • the die shear strength X between the inorganic material layer and the organic material layer is preferably 3 MPa or more, more preferably 4 MPa or more, and even more preferably 5 MPa or more.
  • the upper limit of the die shear strength X between the inorganic material layer and the organic material layer is not particularly limited, but may be, for example, 10 MPa or less, 8 MPa or less, or 6 MPa or less.
  • the adhesive layer preferably contains a cured adhesive.
  • the adhesive layer is sufficiently hard, and misalignment when bonding the inorganic material layer and the organic material layer can be effectively suppressed.
  • the adhesive layer may be in a completely cured state or in a not completely cured state.
  • the curing rate of the adhesive layer may be confirmed, for example, by measuring the peak intensity of a specific bond and structure (the sum of the peak intensities when there are multiple peaks such as imide, amide, etc.) using FT-IR (Fourier transform infrared spectroscopy) in the adhesive layer to be measured and in the fully cured adhesive layer obtained by fully curing the adhesive layer, and determining the rate of increase or decrease in the peak intensity.
  • FT-IR Fastier transform infrared spectroscopy
  • the increase rate of the peak strength may be calculated by the following formula, and the calculated value may be regarded as the curing rate of the adhesive layer.
  • Peak strength increase rate (curing rate of adhesive layer) [(peak strength of specific bonds and structures of adhesive layer to be measured) / (peak strength of specific bonds and structures of completely cured adhesive layer obtained by heating adhesive layer to be measured at 300 ° C. for 1 hour)] ⁇ 100
  • the background signal can be removed by a conventional method. If necessary, the FT-IR measurement can be performed by a transmission method or a reflection method.
  • the peak intensity may be interpreted as the total intensity of the multiple peak intensities.
  • the method for curing the adhesive is not particularly limited and can be selected depending on the composition of the adhesive composition.
  • the heating temperature is not particularly limited, but can be, for example, 150° C. or higher and 350° C. or lower.
  • the laminate of the present disclosure has good uniformity for application to an organic substrate, which is an organic material layer, and therefore can reliably bond an organic substrate to an inorganic substrate, which is an inorganic material layer, and can be applied to a variety of applications.
  • eheODPA crosslinking agent (B)
  • ethanol 30% by mass of ethanol
  • eheODPA ethyl oxydiphthalate half ester
  • ODPA oxydiphthalic anhydride
  • a 4-inch diameter silicon substrate was prepared as a first substrate.
  • the silicon substrate was treated with UV ozone for 5 minutes, and then the composition prepared in (1) above was spin-coated thereon. After drying at 150° C. for 1 minute, the coating was heated at 200° C. for 1 hour in a nitrogen atmosphere to form a film (adhesive layer) containing imide cross-linked siloxane.
  • the substrates were heated in an inert oven at 200° C. for 1 hour to produce a substrate laminate consisting of a first substrate/adhesive layer/second substrate.
  • the surface energy (bonding strength) of the bonding interface of the substrate laminate was measured by a blade insertion test.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

L'invention concerne une composition adhésive qui contient : un composé (A) ayant une liaison Si-O et un groupe fonctionnel cationique comprenant un atome d'azote primaire et/ou un atome d'azote secondaire ; un agent de réticulation (B) qui a un poids moléculaire moyen en poids de 200 à 600 et contient trois groupes -C(=O)OX ou plus dans la molécule, où X représente un atome d'hydrogène ou un groupe alkyle contenant de 1 à 6 atomes de carbone, et un à six des trois groupes -C(=O)OX ou plus est un groupe -C(=O)OH ; et un additif (D) ayant une structure représentée par la formule (a) et une structure représentée par la formule (b). L'invention concerne également un stratifié.
PCT/JP2024/041882 2023-11-30 2024-11-26 Composition adhésive et stratifié Pending WO2025115877A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2023203350 2023-11-30
JP2023-203350 2023-11-30

Publications (1)

Publication Number Publication Date
WO2025115877A1 true WO2025115877A1 (fr) 2025-06-05

Family

ID=95897580

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2024/041882 Pending WO2025115877A1 (fr) 2023-11-30 2024-11-26 Composition adhésive et stratifié

Country Status (1)

Country Link
WO (1) WO2025115877A1 (fr)

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2014095053A (ja) * 2012-11-12 2014-05-22 Nippon Kayaku Co Ltd 硬化性樹脂組成物およびその硬化物
JP2017008146A (ja) * 2015-06-17 2017-01-12 株式会社ダイセル ポリオルガノシルセスキオキサン、ハードコートフィルム、接着シート、積層物及び装置
WO2018079245A1 (fr) * 2016-10-25 2018-05-03 富士フイルム株式会社 Feuille conductrice pour capteur tactile, procédé de fabrication de feuille conductrice pour capteur tactile, capteur tactile, stratifié de panneau tactile, panneau tactile et composition pour former une couche isolante transparente
JP2018070863A (ja) * 2013-12-13 2018-05-10 株式会社ダイセル ポリオルガノシルセスキオキサン、ハードコートフィルム、接着シート、及び積層物
WO2018199117A1 (fr) * 2017-04-28 2018-11-01 三井化学株式会社 Stratifié de substrat et procédé de fabrication de stratifié de substrat
WO2019026458A1 (fr) * 2017-08-02 2019-02-07 東レ株式会社 Composition de résine siloxane, adhésif l'utilisant, dispositif d'affichage, dispositif à semi-conducteurs et dispositif d'éclairage
WO2023032923A1 (fr) * 2021-09-06 2023-03-09 三井化学株式会社 Composition pour former un film pour semi-conducteur, stratifié et stratifié de substrat
WO2023032924A1 (fr) * 2021-09-06 2023-03-09 三井化学株式会社 Composition pour former un film pour semi-conducteur, stratifié et stratifié de substrat

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2014095053A (ja) * 2012-11-12 2014-05-22 Nippon Kayaku Co Ltd 硬化性樹脂組成物およびその硬化物
JP2018070863A (ja) * 2013-12-13 2018-05-10 株式会社ダイセル ポリオルガノシルセスキオキサン、ハードコートフィルム、接着シート、及び積層物
JP2017008146A (ja) * 2015-06-17 2017-01-12 株式会社ダイセル ポリオルガノシルセスキオキサン、ハードコートフィルム、接着シート、積層物及び装置
WO2018079245A1 (fr) * 2016-10-25 2018-05-03 富士フイルム株式会社 Feuille conductrice pour capteur tactile, procédé de fabrication de feuille conductrice pour capteur tactile, capteur tactile, stratifié de panneau tactile, panneau tactile et composition pour former une couche isolante transparente
WO2018199117A1 (fr) * 2017-04-28 2018-11-01 三井化学株式会社 Stratifié de substrat et procédé de fabrication de stratifié de substrat
WO2019026458A1 (fr) * 2017-08-02 2019-02-07 東レ株式会社 Composition de résine siloxane, adhésif l'utilisant, dispositif d'affichage, dispositif à semi-conducteurs et dispositif d'éclairage
WO2023032923A1 (fr) * 2021-09-06 2023-03-09 三井化学株式会社 Composition pour former un film pour semi-conducteur, stratifié et stratifié de substrat
WO2023032924A1 (fr) * 2021-09-06 2023-03-09 三井化学株式会社 Composition pour former un film pour semi-conducteur, stratifié et stratifié de substrat

Similar Documents

Publication Publication Date Title
JP7351019B2 (ja) 組成物、積層体及び積層体の製造方法
CN108352320B (zh) 半导体用膜组合物、各制造方法以及半导体装置
JP6781827B2 (ja) 基板積層体及び基板積層体の製造方法
TW202425072A (zh) 基板積層體的製造方法及半導體裝置
JP7772806B2 (ja) 半導体用の膜を形成するための組成物、積層体及び基板積層体
JP7761656B2 (ja) 半導体用の膜を形成するための組成物、積層体及び基板積層体
WO2025115877A1 (fr) Composition adhésive et stratifié
JP2023177917A (ja) 半導体装置およびその製造方法
WO2025023139A1 (fr) Stratifié et procédé de production de stratifié
TW202544123A (zh) 接著劑用組成物及積層體
JP2025101661A (ja) 積層体及び積層体の製造方法
JP6471879B2 (ja) 樹脂組成物及びそれを用いたパターン形成方法、並びに重合体の合成方法
WO2024166789A1 (fr) Structure semi-conductrice et son procédé de production
JP2025086712A (ja) 組成物、積層体、及び、積層体の製造方法
TW202432357A (zh) 基板積層體的製造方法、積層體以及基板積層體
TW202450057A (zh) 半導體結構體及其製造方法
WO2024162446A1 (fr) Structure semi-conductrice et son procédé de fabrication
TW202510125A (zh) 半導體結構體及其製造方法
JP2025064295A (ja) 基板積層体の製造方法
WO2025005084A1 (fr) Stratifié de substrat
WO2024177116A1 (fr) Procédé de production de puce semi-conductrice avec couche de résine et procédé de production de stratifié de substrat

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: 24897561

Country of ref document: EP

Kind code of ref document: A1