WO2023054449A1 - Adhésif durcissable de type feuille et élément optique - Google Patents

Adhésif durcissable de type feuille et élément optique Download PDF

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Publication number
WO2023054449A1
WO2023054449A1 PCT/JP2022/036115 JP2022036115W WO2023054449A1 WO 2023054449 A1 WO2023054449 A1 WO 2023054449A1 JP 2022036115 W JP2022036115 W JP 2022036115W WO 2023054449 A1 WO2023054449 A1 WO 2023054449A1
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Prior art keywords
sheet
curable adhesive
component
group
adhesive according
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PCT/JP2022/036115
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English (en)
Japanese (ja)
Inventor
樹 長谷川
健太 西嶋
幹広 樫尾
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リンテック株式会社
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Application filed by リンテック株式会社 filed Critical リンテック株式会社
Priority to CN202280063557.2A priority Critical patent/CN118019817A/zh
Priority to KR1020247010167A priority patent/KR20240065096A/ko
Priority to JP2023551586A priority patent/JP7530524B2/ja
Publication of WO2023054449A1 publication Critical patent/WO2023054449A1/fr

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    • 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
    • C09J171/00—Adhesives based on polyethers obtained by reactions forming an ether link in the main chain; Adhesives based on derivatives of such polymers
    • 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
    • C08K3/011—Crosslinking or vulcanising agents, e.g. accelerators
    • 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
    • C08K3/10—Metal compounds
    • 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
    • C09J11/04—Non-macromolecular additives inorganic
    • 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
    • C09J163/00—Adhesives based on epoxy resins; Adhesives based on 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
    • C09J171/00—Adhesives based on polyethers obtained by reactions forming an ether link in the main chain; Adhesives based on derivatives of such polymers
    • C09J171/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
    • C09J171/10—Polyethers derived from hydroxy compounds or from their metallic derivatives from phenols
    • 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
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
    • 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
    • C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
    • C09J2203/318—Applications of adhesives in processes or use of adhesives in the form of films or foils for the production of liquid crystal displays
    • 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
    • C09J2301/00—Additional features of adhesives in the form of films or foils
    • C09J2301/30—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
    • C09J2301/312—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier parameters being the characterizing feature

Definitions

  • the present invention relates to sheet-like curable adhesives, optical members, and the like.
  • Patent Document 1 describes an invention relating to an organic electronic device including a substrate on which an organic light emitting element is formed and an adhesive film that seals the entire surface of the organic light emitting element on the substrate.
  • the adhesive film includes an adhesive layer, and the adhesive layer is a photocured product of a photocurable adhesive composition containing an acrylic polymer, an epoxy resin, and a cationic photopolymerization initiator. It is stated to contain
  • the sheet-shaped curable adhesive according to the present invention is formed from an adhesive composition containing a phenoxy resin having a hydroxyl group and a cyclic ether group-containing compound that is liquid at room temperature, and has a gel fraction of 15% or more. is adjusted so that The present invention provides, for example, an electropeeling pressure-sensitive adhesive sheet having the following aspects.
  • a cured sheet formed from an adhesive composition containing a phenoxy resin (A) having a hydroxyl group and a cyclic ether group-containing compound (B) that is liquid at room temperature and having a gel fraction of 15% or more. adhesive.
  • a sheet-like curable adhesive that can suppress bleeding out is provided.
  • the "active ingredient" of the adhesive composition means, among the ingredients contained in the adhesive composition, the ingredients excluding water and diluent solvents such as organic solvents.
  • the weight average molecular weight (Mw) is a polystyrene-equivalent value measured by gel permeation chromatography (GPC) using tetrahydrofuran (THF) as a solvent.
  • viscosity is a value measured using a rotational viscometer in accordance with JIS Z8803:2011. Specifically, based on the description of Examples below, a Brookfield viscometer (analog viscometer RVT) was used, measurement temperature: 23° C., spindle: No. 5. Number of revolutions: measured at 20 rpm.
  • the sheet-shaped curable adhesive is formed from an adhesive composition containing a phenoxy resin (A) having a hydroxyl group and a cyclic ether group-containing compound (B) that is liquid at room temperature. At this time, the gel fraction of the sheet-like curable adhesive is 15% or more.
  • the “sheet-like curable adhesive” means an adhesive that exhibits non-fluidity at room temperature (23° C.) and is formed into a sheet-like shape.
  • a sheet-like curable adhesive can be formed, for example, by applying an adhesive composition to form a coating film and drying the coating film.
  • the adhesive composition contains a component (A) that is highly compatible with the component (B), and by controlling the gel fraction of the obtained sheet-shaped curable adhesive, the sheet-shaped curable adhesion Bleeding out of the component (B) from the agent can be suppressed.
  • bleed out means that the sheet-shaped curable adhesive may be damaged when stored in a high temperature and high humidity environment or in a pressurized environment, or when stored for a long time in a room temperature environment. It refers to a phenomenon in which various components, such as the component (B) that is absorbed, ooze out onto the surface of the sheet-shaped curable adhesive.
  • the sheet-like curable adhesive has a gel fraction of 15% or more, preferably 20% or more, more preferably 30% or more, and still more preferably 40% or more.
  • the gel fraction of the sheet-like curable adhesive is usually 90% or less, preferably 80% or less, more preferably 70% or less.
  • the content of component (B) in the sheet-shaped curable adhesive layer is increased, the gel fraction of the sheet-shaped curable adhesive tends to decrease. If the upper limit is such a value, it becomes easy to include a desired amount of the component (B) in the sheet-like curable adhesive layer.
  • the "gel fraction" is measured by the method described in Examples.
  • Sheet-like curable adhesives are used for optical applications such as organic EL (electroluminescence) devices and micro LED devices. That is, the sheet-like curable adhesive is preferably used for optical members.
  • the thickness of the sheet-shaped curable adhesive is 1 to 200 ⁇ m from the viewpoint that it can be used for applications that require thinness, such as small and medium-sized displays, and applications that require thickness, such as chip sealing applications for micro LEDs. , more preferably 3 to 175 ⁇ m, even more preferably 10 to 150 ⁇ m.
  • the thickness of the sheet-shaped curable adhesive can be measured according to JIS K7130:1999 using a known thickness meter.
  • the thickness of the optical sheet-like adhesive is the thickness excluding the thickness of the release material.
  • the sheet-like curable adhesive preferably has a low storage modulus. Due to the low storage modulus, the sheet-like curable adhesive can be easily applied to an adherend without peeling off even at room temperature.
  • the storage elastic modulus of the sheet-like curable adhesive at 23° C. is preferably 10 MPa or less, more preferably 5 MPa or less.
  • the storage elastic modulus of the cured product at 23° C. is preferably 0.01 MPa or more, more preferably 0.05 MPa or more.
  • the "storage modulus of the sheet-like curable adhesive at 23°C" is measured by the method described in Examples.
  • the adhesive composition which is a material for forming the sheet-shaped curable adhesive of the present invention, contains a phenoxy resin (A) having a hydroxyl group and a cyclic ether group-containing compound (B) which is liquid at room temperature.
  • the adhesive composition used in one aspect of the present invention further includes a resin other than the component (A), a photocationic polymerization initiator (C), and a cross-linking agent (D) having a functional group capable of reacting with a hydroxyl group.
  • a cross-linking catalyst (E) may be further contained.
  • the total content of components (A) and (B) is preferably 70 mass with respect to the total amount (100 mass%) of the active ingredients of the adhesive composition. % or more, more preferably 80 mass % or more, still more preferably 90 mass % or more, still more preferably 95 mass % or more.
  • the upper limit of the total content of components (A) and (B) is not particularly limited, and is 100% by mass or less and 99.5% by mass with respect to the total amount (100% by mass) of the active ingredients of the adhesive composition. or less, or 99% by mass or less.
  • the total content of components (A), (B), (C), (D), and (E) is the total amount of active ingredients in the adhesive composition (100% by mass), preferably 90% by mass or more, more preferably 95% by mass or more, and even more preferably 98% by mass or more.
  • the upper limit of the total content of components (A), (B), (C), (D), and (E) is not particularly limited, and the total amount (100% by mass) of the active ingredients of the adhesive composition On the other hand, it may be 100% by mass or less, 99.5% by mass or less, or 99% by mass or less.
  • Component (A) phenoxy resin having a hydroxyl group
  • the phenoxy resin (A) having a hydroxyl group (hereinafter also referred to as "component (A)”) has a function of retaining the shape of the sheet-like curable adhesive, a function of imparting flexibility, and the like.
  • component (A) has excellent compatibility with component (B), which will be described later, bleeding out of component (B) from the sheet-like curable adhesive is suppressed, and a sheet having excellent transparency is obtained.
  • a curable adhesive can be obtained.
  • component (A) has excellent heat resistance, a sheet-like curable adhesive with high heat resistance can be obtained.
  • the component (A) can provide a sheet-like curable adhesive having a high storage elastic modulus after curing, it can be suitably used for encapsulation of organic EL elements where such properties are required.
  • Component (A) includes a reaction product of an aromatic diol and at least one selected from aromatic diglycidyl ether compounds and epihalohydrin.
  • aromatic diol examples include compounds having two hydroxyl groups in a substituted or unsubstituted aromatic ring having 6 to 30 ring-forming carbon atoms.
  • aromatic ring having 3 to 30 ring-forming carbon atoms include benzene ring, naphthalene ring, fluorene ring, anthracene ring, phenanthrene ring, biphenyl ring, and combinations of these rings.
  • a specific aromatic diol is preferably a compound represented by the following general formula (a-1).
  • A is a divalent linking group, for example, an optionally substituted alkylene group, an optionally substituted cycloalkylene group, —O—, or and S-.
  • an alkylene group having 1 to 10 carbon atoms is preferable.
  • the alkylene group include a methylene group, an ethylene group, a propylene group, an isopropylene group, and a butylene group.
  • the cycloalkylene group includes a cycloalkylene group having 3 to 6 carbon atoms.
  • Specific examples of the cycloalkylene group include a cyclopropylene group, a cyclobutylene group, a cyclopentylene group, a cyclohexylene group and the like.
  • the substituent is not particularly limited, but an aryl group having 6 to 20 carbon atoms (phenyl group, naphthyl group, etc.), heteroaryl having 3 to 20 carbon atoms group (pyrrolyl group, pyridyl group, etc.), alkoxy group having 1 to 10 carbon atoms (methoxy group, ethoxy group, propyloxy group, etc.), halogen atom (fluorine atom, chlorine atom, bromine atom, iodine atom, etc.), nitro group , a cyano group, and the like.
  • One of these substituents may be substituted, or two or more may be substituted in combination.
  • A is preferably a divalent linking group shown below. (In the above formula, * indicates the bonding position.)
  • aromatic diols include, but are not limited to, benzene ring-containing diols such as hydroquinone, 2-bromohydroquinone, resorcinol, and catechol; 2,2-bis(4-hydroxyphenyl)propane (bisphenol A); 2-bis(4-hydroxyphenyl)butane (bisphenol B), 2,2-bis(4-hydroxy-3-methylphenyl)propane (bisphenol C), 1,1-bis(4-hydroxyphenyl)ethane (bisphenol E), phenylalkylbenzene ring-containing diols such as bis(4-hydroxyphenyl)methane (bisphenol F) and 1,1-bis(4-hydroxyphenyl)cyclohexane (bisphenol Z); phenyloxybenzene ring-containing diols; phenylthiobenzene ring-containing diols such as bis(4-hydroxyphenyl) sulfide; biphenyl group-containing diol
  • Aromatic diglycidyl ether compounds include compounds having two glycidyl groups in a substituted or unsubstituted aromatic ring having 6 to 30 carbon atoms.
  • the substituted or unsubstituted aromatic ring having 6 to 30 carbon atoms is the same as described above.
  • the aromatic diglycidyl compound has a structure in which two hydrogen atoms of the above-mentioned substituted or unsubstituted aromatic ring having 6 to 30 carbon atoms are substituted with glycidyl groups.
  • aromatic diglycidyl compounds include bisphenol A diglycidyl ether, bisphenol B diglycidyl ether, bisphenol C diglycidyl ether, bisphenol E diglycidyl ether, and bisphenol F diglycidyl ether. These aromatic diglycidyl compounds may be used alone or in combination of two or more.
  • Epihalohydrin includes, for example, epichlorohydrin, epibromohydrin, epiiodohydrin, and the like. These epihalohydrins may be used alone or in combination of two or more.
  • the weight average molecular weight of component (A) is preferably 10,000 or more, more preferably 20,000 or more, still more preferably 30,000 or more, and preferably 300,000 or less, more preferably 200,000. 100,000 or less, more preferably 100,000 or less. In one embodiment, the weight average molecular weight of component (A) is preferably 10,000 to 300,000, more preferably 20,000 to 200,000, even more preferably 30,000 to 100,000.
  • the glass transition temperature (Tg) of component (A) is preferably 50°C or higher, more preferably 60°C or higher. Also, the glass transition temperature (Tg) of component (A) is preferably 200° C. or lower, more preferably 180° C. or lower. If the glass transition temperature (Tg) is 50° C. or higher, the flowability of the sheet-shaped curable adhesive is reduced, and bleeding out can be further suppressed. can have a higher storage modulus.
  • the content of component (A) is preferably 20% or more, preferably 30% or more, relative to the total amount of active ingredients (100% by mass), from the viewpoint of increasing the shape retention of the sheet-shaped curable adhesive. is more preferably 40% or more.
  • the content of component (A) is preferably 75% or less, preferably 65% or less, relative to the total mass of the adhesive composition, from the viewpoint of increasing the content of component (B). is more preferred.
  • the hydroxyl equivalent (g/eq) of component (A) is usually 50 to 1,000 g/eq, preferably 100 to 750 g/eq, more preferably 200 to 500 g/eq.
  • the adhesive composition may contain other resins than component (A). By including other resins in the adhesive composition, the physical properties of the sheet-like curable adhesive can be adjusted.
  • another resin means a resin other than component (A), and its weight average molecular weight is usually 10,000 or more.
  • resins include, but are not particularly limited to, olefin resins, acrylic resins, polyester resins, polyvinyl alcohol resins, polyvinyl acetal resins, polyvinyl chloride, polyamide resins, cellulosic materials, polyvinyl ethers, polyimide resins, styrene resins, and the like. and a copolymer containing a resin constitutional unit. These other resins may be used alone or in combination of two or more.
  • the content of the other resin is preferably less than 50 parts by mass, more preferably less than 20 parts by mass, more preferably less than 10 parts by mass, and still more preferably 5 parts by mass with respect to 100 parts by mass of the total amount of component (A). It is less than parts by mass.
  • Component (B) Cyclic ether group-containing compound that is liquid at room temperature
  • the cyclic ether group-containing compound (B) (hereinafter also referred to as “component (B)"), which is liquid at room temperature, is contained in the sheet-shaped curable adhesive, thereby imparting a function as a curable adhesive. do. Since the component (B) is a liquid at room temperature, the sheet-shaped curable adhesive has excellent room-temperature sticking properties. The reactivity with is high, and it can have effects such as no uncured component (B) remaining in the cured product.
  • the term "liquid at room temperature” means fluid at 23°C, that is, having a viscosity of 10,000 mPa ⁇ s or less at 23°C.
  • Component (B) is not particularly limited, but includes cyclic ether group-containing chain alkyl compounds, cyclic ether group-containing alicyclic alkyl compounds, cyclic ether group-containing aromatic compounds, and cyclic ether group-containing polyoxyalkylene compounds. .
  • Cyclic ether group-containing chain alkyl compounds include reaction products of substituted or unsubstituted chain alkyl polyols and cyclic ether group-containing compounds.
  • Chain alkyl polyols are not particularly limited, but alkanediols having 1 to 10 carbon atoms such as methanediol, ethylene glycol, propylene glycol, 1,4-butanediol and neopentyl glycol; carbon atoms such as glycerin and trimethylolpropane; alkanetriols having 1 to 10 carbon atoms; erythritol, pentaerythritol, sorbitol and alkanepolyols having 1 to 10 carbon atoms.
  • the chain alkyl polyol is preferably an alkyl diol having 1 to 10 carbon atoms, more preferably ethylene glycol, propylene glycol and 1,4-butanediol.
  • the substituent is not particularly limited, but an alkoxy group having 1 to 10 carbon atoms (methoxy group, ethoxy group, propyloxy group, etc.), a halogen atom (fluorine atom, chlorine atom , bromine atom, iodine atom, etc.), a nitro group, a cyano group, and the like.
  • One of these substituents may be substituted, or two or more may be substituted in combination.
  • the cyclic ether group-containing compound is not particularly limited, but a three-membered cyclic ether group (oxirane)-containing compound such as epichlorohydrin, epibromohydrin, epiiodohydrin; 3-(chloromethyl)-3- 4-membered cyclic ether group (oxetane)-containing compounds such as methyloxetane, 3-(bromomethyl)-3-methyloxetane, and the like.
  • the cyclic ether group-containing compound is preferably a three-membered cyclic ether group (oxirane)-containing compound, more preferably epichlorohydrin or epibromohydrin.
  • Cyclic ether group-containing alicyclic alkyl compounds include reaction products of substituted or unsubstituted cyclic alkyl polyols and cyclic ether group-containing compounds.
  • Cyclic alkyl polyols are not particularly limited, but include 1,2-cyclopropanediol, 1,2-cyclobutanediol, 1,2-cyclopentanediol, 1,2-cyclohexanediol, 1,4-cyclohexanediol, 1, cycloalkyldiols having 3 to 10 carbon atoms such as 2-cyclopentanediol, 1,3-cyclopentanediol and hydrogenated bisphenol A; cycloalkanetriols having 3 to 10 carbon atoms such as 1,3,5-cyclohexanetriol; Cycloalkanepolyols having 3 to 10 carbon atoms such as 1,2,3,4-cyclohexanetetraol can be mentioned.
  • the alicyclic alkyl compound is preferably a cycloalkyldiol having 3 to 10 carbon atoms, more preferably hydrogenated bisphenol A.
  • the substituent is not particularly limited. Examples thereof include alkoxy groups (methoxy group, ethoxy group, propyloxy group, etc.), halogen atoms (fluorine atom, chlorine atom, bromine atom, iodine atom, etc.), nitro group, cyano group and the like.
  • substituents may be substituted, or two or more may be substituted in combination.
  • the cyclic ether group-containing compound is not particularly limited, but a three-membered cyclic ether group (oxirane)-containing compound such as epichlorohydrin, epibromohydrin, epiiodohydrin; 3-(chloromethyl)-3- 4-membered cyclic ether group (oxetane)-containing compounds such as methyloxetane, 3-(bromomethyl)-3-methyloxetane, and the like.
  • the cyclic ether group-containing compound is preferably a three-membered cyclic ether group (oxirane)-containing compound, more preferably epichlorohydrin or epibromohydrin.
  • Cyclic ether group-containing aromatic compounds include reaction products of substituted or unsubstituted aromatic polyols and cyclic ether group-containing compounds.
  • the aromatic polyol is not particularly limited, but includes the aromatic diols described in the description of component (A); aromatic triols such as 1,3,5-benzenetriol.
  • the aromatic polyol is preferably an aromatic diol, more preferably a phenylalkylbenzene ring-containing diol, and even more preferably bisphenol A, bisphenol B, bisphenol C, and bisphenol F.
  • the aromatic polyol has a substituent, the substituent is not particularly limited.
  • alkoxy groups methoxy group, ethoxy group, propyloxy group, etc.
  • halogen atoms fluorine atom, chlorine atom, bromine atom, iodine atom, etc.
  • nitro group cyano group and the like.
  • substituents may be substituted, or two or more may be substituted in combination.
  • the said substituent usually substitutes with the hydrogen atom of the aromatic ring of aromatic polyol.
  • the cyclic ether group-containing compound is not particularly limited, but a three-membered cyclic ether group (oxirane)-containing compound such as epichlorohydrin, epibromohydrin, epiiodohydrin; 3-(chloromethyl)-3- 4-membered cyclic ether group (oxetane)-containing compounds such as methyloxetane, 3-(bromomethyl)-3-methyloxetane, and the like.
  • the cyclic ether group-containing compound is preferably a three-membered cyclic ether group (oxirane)-containing compound, more preferably epichlorohydrin or epibromohydrin.
  • Cyclic ether group-containing polyoxyalkylene compounds include reaction products of substituted or unsubstituted (poly)oxyalkylene polyols and cyclic ether group-containing compounds.
  • the (poly)oxyalkylene polyol repeating alkanediols having 1 to 10 carbon atoms such as (poly)ethylene glycol, (poly)propylene glycol, (poly)butylene glycol, (poly)oxyethylene (poly)oxypropylene glycol, etc.
  • a compound having as a unit can be mentioned.
  • the cyclic ether group-containing compound is not particularly limited, but epichlorohydrin, epibromohydrin, epiiodohydrin, aromatic diglycidyl compounds (bisphenol A diglycidyl ether, bisphenol B diglycidyl ether, bisphenol C diglycidyl ether , bisphenol E diglycidyl ether, bisphenol F diglycidyl ether, etc.) 3-membered cyclic ether group (oxirane)-containing compounds; 3-(chloromethyl)-3-methyloxetane, 3-(bromomethyl)-3-methyloxetane 4-membered cyclic ether group (oxetane)-containing compounds such as Among these, the cyclic ether group-containing compound is preferably a three-membered cyclic ether group (oxirane)-containing compound, more preferably epichlorohydrin, epibromohydrin, or an aromatic diglycidyl compound.
  • the component (B) may
  • the weight-average molecular weight of the component (B) is appropriately set so that the component (B) is liquid at room temperature. , less than 5,000, 4,000 or less, 3,000 or less, 2,000 or less, 1,000 or less, or 800 or less.
  • the glass transition temperature (Tg) of the homopolymer is preferably 25°C or lower, more preferably 5°C or lower, and still more preferably -20°C.
  • component (B) includes a homopolymer having a glass transition temperature (Tg) of preferably ⁇ 100° C. or higher, more preferably ⁇ 80° C. or higher.
  • Tg glass transition temperature
  • the glass transition temperature (Tg) of the homopolymer is 25° C. or less, because the reactivity of the cyclic ether group of the component (B) increases. .
  • the reaction proceeds favorably without heating, and the resulting cured product contains little or no unreacted component (B). It is preferable because there is no
  • the glass transition temperature (Tg) of the component (B) homopolymer tends to be 25° C. or lower when the component (B) has a sparse molecular structure and is flexible.
  • the glass transition temperature (Tg) of the homopolymer can be 25° C. or lower, which is preferable.
  • Glass transition temperature (Tg) of a homopolymer when it is made into a homopolymer means the glass transition temperature of the homopolymer (cured product) obtained when the component (B) is cured by the following method and measured. means temperature (Tg).
  • Tg glass transition temperature
  • a thermal cationic polymerization initiator manufactured by Sanshin Chemical Industry Co., Ltd., trade name: SI-B3A
  • SI-B3A thermal cationic polymerization initiator
  • differential scanning calorimetry Using a differential scanning calorimeter [manufactured by TA Instruments, product name: DSCQ2000], differential scanning calorimetry is performed by the following method, and then the glass transition temperature is determined. That is, 5 mg of the measurement sample is crushed, placed in an aluminum pan, sealed by pressing the lid, held at 120° C. for 5 minutes, and then cooled. After that, the temperature is measured from 100° C. to +120° C. at a heating rate of 10° C./min.
  • the epoxy equivalent of component (B) is preferably 75 g/eq or more, more preferably 150 g/eq or more.
  • the epoxy equivalent of component (B) is preferably 600 g/eq or less, more preferably 500 g/eq or less.
  • the viscosity of component (B) at 23°C is preferably 10 mPa ⁇ s or more.
  • the upper limit of the viscosity of the component (B) at 23 ° C. is usually 10,000 mPa s or less, and the sheet-like curable adhesive is When a cationic polymerization initiator is included, it is preferably 5,000 mPa s or less, more preferably 3,000 mPa s or less, from the viewpoint of increasing the reactivity between the cation and the cyclic ether during the curing reaction. , 1,000 mPa ⁇ s or less.
  • the viscosity of component (B) at 23° C. is preferably from 10 to 5,000 mPa ⁇ s, more preferably from 10 to 1,000 mPa ⁇ s.
  • the content of component (B) is preferably 40 parts by mass or more, more preferably 50 parts by mass or more, relative to 100 parts by mass of component (A).
  • the content of component (B) is preferably 200 parts by mass or less, more preferably 150 parts by mass or less, per 100 parts by mass of component (A).
  • the content of component (B) is preferably 40 to 200 parts by mass, more preferably 50 to 150 parts by mass, per 100 parts by mass of component (A).
  • Component (C) photo cationic polymerization initiator
  • the adhesive composition preferably further contains a photocationic polymerization initiator (C) (hereinafter also referred to as "component (C)").
  • Component (C) has a function of favorably advancing the polymerization reaction of component (B) and the like when the sheet-like curable adhesive is used, and a function of improving the storage stability of the sheet-like curable adhesive.
  • Component (C) generates cationic species upon irradiation with light to initiate the polymerization reaction of component (B) and the like.
  • Component (C) is not particularly limited, but includes sulfonium salt compounds, iodonium salt compounds, phosphonium salt compounds, ammonium salt compounds, diazonium salt compounds, selenium salt compounds, oxonium salt compounds, and bromine salt compounds. compounds and the like.
  • the sulfonium salt compound is not particularly limited, but (4-(phenylthio)phenyldiphenylsulfonium hexafluorophosphate, triphenylsulfonium hexafluorophosphate, triphenylsulfonium hexafluoroantimonate, triphenylsulfonium tetrakis(pentafluorophenyl)borate , 4,4′-bis[diphenylsulfonio]diphenylsulfide-bishexafluorophosphate and the like.
  • iodonium salt compounds include, but are not limited to, diphenyliodonium tetrakis(pentafluorophenyl)borate, diphenyliodonium hexafluorophosphate, diphenyliodonium hexafluoroantimonate, di(4-nonylphenyl)iodonium hexafluorophosphate, (tricumyl). and iodonium tetrakis(pentafluorophenyl)borate. is mentioned.
  • Phosphonium salt compounds include, but are not limited to, tri-n-butyl(2,5-dihydroxyphenyl)phosphonium bromide, hexadecyltributylphosphonium chloride, and the like.
  • ammonium salt compounds include, but are not limited to, benzyltrimethylammonium chloride, phenyltributylammonium chloride, benzyltrimethylammonium bromide, and the like.
  • the above component (C) may be used alone or in combination of two or more.
  • the content of component (C) is preferably 0.1% by mass or more, more preferably 0.3% by mass or more, relative to the total amount (100% by mass) of the active ingredients in the adhesive composition. preferable.
  • the upper limit of the content of component (C) is preferably 3% by mass or less, more preferably 2% by mass or less.
  • Component (D) a cross-linking agent having a functional group capable of reacting with a hydroxyl group
  • the adhesive composition preferably further contains a cross-linking agent (D) having a functional group capable of reacting with a hydroxyl group (hereinafter also referred to as "component (D)").
  • Component (D) has the function of forming a crosslinked structure by reacting with the hydroxyl groups of component (A) when the sheet-like curable adhesive is formed. Thereby, the gel fraction of the obtained sheet-like curable adhesive can be increased, and bleed-out can be effectively suppressed.
  • the isocyanate-based cross-linking agent (D1) is not particularly limited, but aromatics such as phenylene diisocyanate, tolylene diisocyanate (TDI), xylylene diisocyanate (XDI), diphenylmethane diisocyanate (MDI), triphenylmethane triisocyanate, and naphthalene diisocyanate aliphatic isocyanates such as pentamethylene diisocyanate (PDI), hexamethylene diisocyanate (HDI), isophorone diisocyanate (IPDI), hydrogenated products of the above aromatic isocyanates; dimers (biuret), trimers ( isocyanurate), pentamers; trimethylolpropane (TMP) adducts thereof, and the like.
  • aromatics such as phenylene diisocyanate, tolylene diisocyanate (TDI), xylylene diisocyanate (XDI), di
  • acid anhydride cross-linking agents (D2) examples include phthalic anhydride, methyltetrahydrophthalic anhydride, hexahydrophthalic anhydride, pyromellitic anhydride, trimellitic anhydride, methylnadic anhydride, 1,3,3a.
  • cross-linking agent (D2) which is an acid anhydride, may be used alone or in combination of two or more. Also, one or more of the above-mentioned isocyanate-based crosslinking agents (D1) and one or more of the above-mentioned acid anhydride crosslinking agents (D2) may be used in combination.
  • the content of component (D) is preferably 0.3 parts by mass or more, more preferably 0.5 parts by mass or more, and 1 part by mass or more with respect to 100 parts by mass of component (A). It is even more preferable to have In addition, the content of component (D) is preferably 15 parts by mass or less, more preferably 10 parts by mass or less, and 8 parts by mass or less with respect to 100 parts by mass of component (A). is more preferred.
  • Component (E) Crosslinking catalyst
  • the adhesive composition preferably further contains a cross-linking catalyst (E) (hereinafter also referred to as "component (E)").
  • Component (E) has the function of promoting the cross-linking reaction between the hydroxyl groups of component (A) and the functional groups capable of reacting with the hydroxyl groups of component (D) during the formation of the sheet-like curable adhesive.
  • the hydroxyl group of component (A) is preferably derived from an aromatic diglycidyl ether compound or epihalohydrin, and thus is a secondary hydroxyl group and tends to have low reactivity due to steric hindrance.
  • a cross-linked structure By promoting the cross-linking reaction between the component (A) and the component (D) in the presence of the component (E), a cross-linked structure can be preferably formed. As a result, it is possible to increase the gel fraction of the obtained sheet-shaped curable adhesive, and to suppress bleeding out.
  • the component (E) is not particularly limited, but includes metal chelate compounds, metal alkoxides, and the like. Among these, the component (E) preferably contains the metal chelate compound (E1).
  • a metal chelate compound (E1) contains a metal and a ligand.
  • the metal chelate compound (E1) preferably contains a metal selected from the group consisting of aluminum, bismuth, iron, zirconium, and zinc, and contains a metal selected from the group consisting of iron, zirconium, and zinc. More preferably, it contains iron and/or zinc. Including these metals in the component (E) is preferable because the speed of the cross-linking reaction of the component (A) and the component (D) is increased.
  • ligands include acetylacetone, hexane-2,4-dione, heptane-2,4-dione, heptane-3,5-dione, 5-methyl-hexane-2,4-dione, octane-2, ⁇ -diketones such as 4-dione, 6-methylheptane-2,4-dione, 2,6-dimethylheptane-3,5-dione; methyl acetoacetate, ethyl acetoacetate, n-propyl acetoacetate, acetoacetate ⁇ -Ketoesters such as isopropyl, n-butyl acetoacetate, sec-butyl acetoacetate, tert-butyl acetoacetate, methyl propionylacetate and ethyl propionylacetate.
  • ⁇ -diketones such as 4-dione, 6-methylheptane-2,4-d
  • the content of component (E) is preferably 0.001 parts by mass or more, more preferably 0.005 parts by mass or more, relative to 100 parts by mass of component (A).
  • the content of component (E) is preferably 3 parts by mass or less, more preferably 1 part by mass or less, per 100 parts by mass of component (A).
  • the content ratio of component (E) to component (D) [(E)/(D)] is preferably 0.001 or more, more preferably 0.003 or more.
  • the content ratio [(E)/(D)] of component (E) to component (D) is preferably 1 or less, more preferably 0.5 or less.
  • the adhesive composition may contain additives.
  • Additives include, but are not limited to, silane coupling agents, ultraviolet absorbers, antistatic agents, light stabilizers, antioxidants, resin stabilizers, fillers, pigments, extenders, softeners, and the like. These additives may be used alone or in combination of two or more.
  • the adhesive composition may contain a solvent.
  • the solvent has the function of imparting fluidity to the adhesive composition. Thereby, a sheet-like curable adhesive can be suitably formed from the adhesive composition.
  • the solvent is not particularly limited, but aromatic hydrocarbon solvents such as benzene and toluene; ester solvents such as ethyl acetate and butyl acetate; ketone solvents such as acetone, methyl ethyl ketone and methyl isobutyl ketone; Aliphatic hydrocarbon solvents such as -hexane and n-heptane; and alicyclic hydrocarbon solvents such as cyclopentane, cyclohexane and methylcyclohexane. These solvents may be used alone or in combination of two or more.
  • aromatic hydrocarbon solvents such as benzene and toluene
  • ester solvents such as ethyl acetate and butyl acetate
  • ketone solvents such as acetone, methyl ethyl ketone and methyl isobutyl ketone
  • Aliphatic hydrocarbon solvents such as -hexane and n-hept
  • the content of the solvent can be appropriately determined in consideration of the composition of the adhesive composition and the manufacturing conditions of the sheet-shaped curable adhesive.
  • the sheet-shaped curable adhesive of the present invention may be sandwiched between two release materials.
  • the release material has a function of preventing unintended adhesion to other members before use, a function of improving handling, and the like. When used, the release material is peeled off from the sheet-like curable adhesive and adhered to various members.
  • the release material may include a release substrate and a release agent layer laminated on one or both sides of the release substrate, the release substrate itself having releasability, and the release agent It may be one without layers.
  • Release substrates include polyimide, polyamide, polyamideimide, polyphenylene ether, polyetherketone, polyetheretherketone, polyolefin, polyester, polycarbonate, polysulfone, polyethersulfone, polyphenylene sulfide, polyarylate, acrylic resin, cycloolefin
  • resin films formed from resins such as poly-based polymers, aromatic polymers, and polyurethane-based polymers.
  • polyester resins are preferred.
  • a resin film formed from a fluororesin or the like can be used as the release base material having releasability.
  • rubber elastomers such as silicone resins, olefin resins, isoprene resins, butadiene resins, resins such as long-chain alkyl resins, alkyd resins, fluorine resins, etc. are used as coating films.
  • the formed layer is mentioned.
  • the thickness of the release material is not particularly limited, it is preferably 5 to 300 ⁇ m, more preferably 10 to 200 ⁇ m, even more preferably 15 to 100 ⁇ m.
  • a sheet-like curable adhesive is formed from the adhesive composition described above.
  • the method for forming the sheet-like curable adhesive is not particularly limited, but examples thereof include a method of applying an adhesive composition to a support and drying the resulting coating film.
  • the support is preferably a release material.
  • the method of applying the adhesive composition is not particularly limited, but includes spin coating, spray coating, bar coating, knife coating, roll coating, blade coating, die coating, gravure coating, and the like.
  • the drying method is not particularly limited, but includes hot air drying, hot roll drying, infrared irradiation and the like.
  • the drying temperature is not particularly limited, it is preferably 80 to 150°C, more preferably 85 to 120°C, even more preferably 90 to 110°C.
  • the drying time is preferably 30 seconds to 5 minutes, more preferably 45 seconds to 4 minutes, even more preferably 1 to 3 minutes.
  • At least part of the cyclic ether functional groups of the component (B) contained in the adhesive composition undergoes a polymerization reaction, thereby improving the shape retention of the sheet-like curable adhesive.
  • the adhesive composition contains the component (D)
  • the cross-linking reaction of the component (A) and the component (D) improves the shape retention of the sheet-shaped curable adhesive and increases the gel fraction. improves.
  • the adhesive composition further contains the component (E)
  • the cross-linking reaction is accelerated, and the time required for gelation can be shortened, resulting in a low production cost. These reactions can be accelerated by the heating that accompanies the drying of the formation reaction.
  • optical member The sheet-like curable adhesive described above is suitably used for optical members. Accordingly, one aspect of the present invention provides an optical member comprising a cured product obtained by curing a sheet-shaped curable adhesive.
  • the curing method is not particularly limited, and may be photocuring, heat curing, or a combination thereof. From the viewpoint of being able to shorten the time required for the curing process, being able to cure the sheet-shaped curable adhesive without heating, and being suitably applicable to devices such as organic EL elements that should avoid high temperatures, the curing method is is preferably photocuring. Since the sheet-shaped curable adhesive contains the cyclic ether group-containing compound (B) that is liquid at room temperature, it has high photocuring reaction reactivity.
  • Photocuring is usually performed by irradiating the sheet-shaped curable adhesive with ultraviolet rays.
  • ultraviolet light sources include light sources such as ultra-high pressure mercury lamps, high pressure mercury lamps, low pressure mercury lamps, carbon arc lamps, black light fluorescent lamps, and metal halide lamps.
  • the wavelength of ultraviolet rays is preferably 190 to 380 nm, for example.
  • the irradiation intensity is preferably, for example, 20 to 1000 mW/cm 2 .
  • the amount of irradiation light is preferably, for example, 50 to 3000 mJ/cm 2 .
  • Thermal curing is usually performed by heating the sheet-like curable adhesive.
  • the heating temperature is, for example, preferably 80 to 200°C, more preferably 90 to 190°C.
  • the heating time is, for example, preferably 30 minutes to 12 hours, more preferably 1 to 6 hours.
  • the cured product obtained by curing the sheet-like curable adhesive preferably has a high storage elastic modulus. Due to the high storage modulus, the sheet-like curable adhesive is less likely to be softened even at high temperatures, and the adhesiveness is less likely to decrease due to temperature changes.
  • the storage elastic modulus of the cured product at 100° C. is preferably 1 ⁇ 10 5 Pa or more, more preferably 2 ⁇ 10 5 Pa or more, and even more preferably 5 ⁇ 10 5 Pa or more.
  • the upper limit of the storage elastic modulus at 100° C. of the cured product is not particularly limited, but is usually 2 ⁇ 10 7 Pa or less.
  • the "storage modulus of the cured product at 100°C” conforms to JIS K7244-6 and is measured by a torsional shear method using a viscoelasticity measuring device (manufactured by Anton refrigerator, product name: MCR302). It is measured by the following method.
  • Sheet-like curable adhesives are layered to obtain a laminate having a thickness of 0.5 mm.
  • the layered body of the sheet-shaped curable adhesive is irradiated with UV to cure the layered body of the sheet-shaped curable adhesive.
  • the laminate is heated at 100° C. for 60 minutes in order to accelerate the curing reaction to obtain a cured product of the sheet-like curable adhesive (laminate).
  • the UV irradiation is performed using a high-pressure mercury lamp manufactured by Eye Graphics Co., Ltd. under the conditions of an illuminance of 200 mW/cm 2 and an integrated light amount of 1000 mJ/cm 2 .
  • UVPF-A1 manufactured by Eye Graphics Co., Ltd.
  • a cured product of the sheet-like curable adhesive (laminate) is punched into a cylindrical body (height: 0.5 mm) with a diameter of 8 mm, and this is used as a measurement sample.
  • Measurement of storage shear modulus Using the obtained measurement sample, the storage modulus of the cured product at 100° C. is measured under the conditions of a frequency of 1 Hz, a test start temperature of ⁇ 20° C., a test end temperature of +150° C., and a heating rate of 3° C./min.
  • the sheet-shaped curable adhesive is attached to the optical members after peeling off the attached release material.
  • the sheet-like curable adhesive according to the present embodiment is excellent in workability due to its excellent stickability at room temperature.
  • the sheet-like curable adhesive By curing the sheet-like curable adhesive to obtain a cured product, it can function as, for example, a sealing layer for an optical member.
  • Weight average molecular weight (Mw) The weight average molecular weight (Mw) of the phenoxy resin as component (A) was measured as a polystyrene-equivalent value by gel permeation chromatography (GPC) using tetrahydrofuran (THF) as a solvent.
  • the viscosity of the epoxy resin constituting component (B) was measured using a rotary viscometer in accordance with JIS Z8803:2011. Specifically, a Brookfield viscometer (analog viscometer RVT) was used, measurement temperature: 23° C., spindle: No. 5. Number of revolutions: Measured under the condition of 20 rpm.
  • the glass transition temperature (Tg) of the cured epoxy resin constituting component (B) was measured by the following method. (Preparation of measurement sample) To 100 parts by mass of each epoxy resin, 0.5 parts by mass of a thermal cationic polymerization initiator [manufactured by Sanshin Chemical Industry Co., Ltd., trade name: SI-B3A] was added. The obtained mixture was poured into a polytetrafluoroethylene mold having a thickness of 1 mm and a size of 20 mm ⁇ 20 mm, and cured by heating at 100° C. for 60 minutes to obtain a cured product (measurement sample).
  • a thermal cationic polymerization initiator manufactured by Sanshin Chemical Industry Co., Ltd., trade name: SI-B3A
  • differential scanning calorimetry Using a differential scanning calorimeter [manufactured by TA Instruments, product name: DSCQ2000], differential scanning calorimetry was performed by the following method, and then the glass transition temperature was determined. That is, 5 mg of the measurement sample was crushed, placed in an aluminum pan, sealed by pressing the lid, held at 120° C. for 5 minutes, and then cooled. After that, the temperature was measured from ⁇ 100° C. to +120° C. at a heating rate of 10° C./min.
  • the temperature at the intersection of a straight line obtained by extending the base line on the low temperature side of the obtained curve to the high temperature side and a tangent line drawn at the point where the gradient of the curve in the stepwise change portion of the glass transition is maximized is the glass transition temperature. temperature (Tg).
  • the time until the gelation of the manufactured adhesive composition was completed was evaluated as the gelation completion time. Specifically, first, the gel fraction of the sheet-like curable adhesive immediately after production was measured. Next, the sheet-shaped curable adhesive was stored under an environment of 23° C. and a relative humidity of 50%, and the gel fraction was measured every day. The number of days elapsed until the rate of change shown by the following formula was within ⁇ 5% was evaluated as the gelation completion time. If there was no substantial change in the gel fraction value from immediately after application until 14 days later, it was judged that the reaction had not progressed.
  • the gel fraction was measured by the following method. That is, the sheet-like curable adhesive with release material was cut into a size of 80 mm ⁇ 80 mm. A test piece was prepared by removing the release material from both sides of the cut release material-attached sheet. In the measurement, the test piece was wrapped in a polyester mesh (product name: Tetoron mesh #200) and weighed with a precision balance, and the weight was calculated by subtracting the weight of the mesh alone (the weight of the test piece before immersion). . Next, the test piece wrapped in the mesh was immersed in methyl ethyl ketone (MEK) at 23° C. for 3 days, then taken out and dried in an oven at 100° C. for 2 hours.
  • MEK methyl ethyl ketone
  • the test piece after immersion was wrapped in a polyester mesh (product name: Tetoron mesh #200) and weighed with a precision balance, and the mass of the mesh alone was subtracted to calculate the weight (mass of the test piece after immersion). .
  • the gel fraction was calculated by the following formula.
  • the gel fraction of the sheet-shaped curable adhesive was the gel fraction after the gelation completion time had elapsed. When it was determined that the reaction had not progressed, the gel fraction of the sheet-shaped curable adhesive 14 days after preparation was taken as the gel fraction.
  • Example 1 Preparation of adhesive composition
  • 2 parts by mass (active ingredient ratio) of CPI-100P and 0.01 parts by mass (active ingredient ratio) of tris(2,4-pentanedionato)iron (III) as a crosslinking catalyst (E) as active ingredients was diluted with methyl ethyl ketone to a concentration of 50% by mass to prepare an adhesive composition.
  • the prepared adhesive composition was applied onto the release-treated surface of a release material SP-PET752150 (manufactured by Lintec Corporation). The obtained coating film was allowed to stand for 2 minutes while blowing air in an environment of 100° C. and dried to produce a sheet-like curable adhesive having a thickness of 25 ⁇ m.
  • the release-treated surface of SP-PET381031 manufactured by Lintec Corporation, which is a release material, is attached, and the sheet-shaped curable adhesive with release material is attached. manufactured.
  • Examples 2-6, Comparative Examples 1-2 A sheet-like curable adhesive with a release material was produced in the same manner as in Example 1, except that the compounds used and the amounts added were changed as shown in Table 1 below. In addition, the gelation completion time and gel fraction were measured by the above methods.
  • the sheet-shaped curable adhesives produced in Comparative Examples 1 and 2 showed no substantial change in the gel fraction values from immediately after application until 14 days after application, so it was judged that the reaction had not progressed. Therefore, in Comparative Examples 1 and 2, the gel fraction after 14 days was used as the gel fraction of the sheet-like curable adhesive.

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

Abstract

La présente invention concerne un adhésif durcissable de type feuille qui peut être supprimé lors du saignement. L'adhésif durcissable de type feuille est constitué d'une composition adhésive qui contient (A) une résine phénoxy ayant un groupe hydroxyle et (B) un composé contenant un groupe éther cyclique qui est dans un état liquide à température ambiante ; et l'adhésif durcissable de type feuille a une fraction gel supérieure ou égale à 15 %.
PCT/JP2022/036115 2021-09-28 2022-09-28 Adhésif durcissable de type feuille et élément optique WO2023054449A1 (fr)

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CN202280063557.2A CN118019817A (zh) 2021-09-28 2022-09-28 片状固化性粘接剂及光学构件
KR1020247010167A KR20240065096A (ko) 2021-09-28 2022-09-28 시트상 경화성 접착제 및 광학 부재
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JPH06166852A (ja) * 1992-10-01 1994-06-14 Nitto Denko Corp 熱硬化性接着シート
JP2004285307A (ja) * 2003-03-25 2004-10-14 Sony Chem Corp 接着剤及び電気装置の製造方法
JP2016060761A (ja) * 2014-09-16 2016-04-25 デクセリアルズ株式会社 異方性導電接着剤、及び接続構造体の製造方法
JP2017504664A (ja) * 2013-11-29 2017-02-09 エルジー・ハウシス・リミテッドＬｇ Ｈａｕｓｙｓ，Ｌｔｄ． 接着フィルム形成用組成物、光硬化前加工用粘着フィルム、接着フィルム及び電子ペーパー表示装置
JP2017179055A (ja) * 2016-03-29 2017-10-05 味の素株式会社 熱硬化性樹脂組成物
WO2019189618A1 (fr) * 2018-03-28 2019-10-03 リンテック株式会社 Corps scellé de dispositif électronique, adhésif en forme de feuille, film adhésif de scellement de dispositif électronique, et procédé de fabrication de corps scellé de dispositif électronique
WO2019240260A1 (fr) * 2018-06-15 2019-12-19 リンテック株式会社 Composition d'étanchéité, feuille d'étanchéité, et corps étanche

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Publication number Priority date Publication date Assignee Title
TWI582202B (zh) 2011-11-18 2017-05-11 Ｌｇ化學股份有限公司 用於封裝有機電子裝置之光可硬化壓感性黏著膜、有機電子裝置及用於封裝有機電子裝置之方法

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH06166852A (ja) * 1992-10-01 1994-06-14 Nitto Denko Corp 熱硬化性接着シート
JP2004285307A (ja) * 2003-03-25 2004-10-14 Sony Chem Corp 接着剤及び電気装置の製造方法
JP2017504664A (ja) * 2013-11-29 2017-02-09 エルジー・ハウシス・リミテッドＬｇ Ｈａｕｓｙｓ，Ｌｔｄ． 接着フィルム形成用組成物、光硬化前加工用粘着フィルム、接着フィルム及び電子ペーパー表示装置
JP2016060761A (ja) * 2014-09-16 2016-04-25 デクセリアルズ株式会社 異方性導電接着剤、及び接続構造体の製造方法
JP2017179055A (ja) * 2016-03-29 2017-10-05 味の素株式会社 熱硬化性樹脂組成物
WO2019189618A1 (fr) * 2018-03-28 2019-10-03 リンテック株式会社 Corps scellé de dispositif électronique, adhésif en forme de feuille, film adhésif de scellement de dispositif électronique, et procédé de fabrication de corps scellé de dispositif électronique
WO2019240260A1 (fr) * 2018-06-15 2019-12-19 リンテック株式会社 Composition d'étanchéité, feuille d'étanchéité, et corps étanche

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