CN112368353B - Adhesive sheet for sealing equipment and method for manufacturing sealing equipment - Google Patents

Adhesive sheet for sealing equipment and method for manufacturing sealing equipment Download PDF

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Publication number
CN112368353B
CN112368353B CN201980040146.XA CN201980040146A CN112368353B CN 112368353 B CN112368353 B CN 112368353B CN 201980040146 A CN201980040146 A CN 201980040146A CN 112368353 B CN112368353 B CN 112368353B
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adhesive layer
adhesive
sealing
release film
adhesive sheet
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CN112368353A (en
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西嶋健太
长谷川树
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Lintec Corp
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Lintec Corp
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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
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/15—Heterocyclic compounds having oxygen in the ring
    • C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
    • C08K5/1515—Three-membered rings
    • 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
    • C09J201/00—Adhesives based on unspecified macromolecular 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
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/10—Adhesives in the form of films or foils without carriers
    • 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
    • C09J7/40—Adhesives in the form of films or foils characterised by release liners
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/02—Details
    • H05B33/04—Sealing arrangements, e.g. against humidity
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/10—Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
    • 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
    • C09J2203/326—Applications of adhesives in processes or use of adhesives in the form of films or foils for bonding electronic components such as wafers, chips or semiconductors
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/80—Constructional details
    • H10K50/84—Passivation; Containers; Encapsulations
    • H10K50/842—Containers
    • H10K50/8426—Peripheral sealing arrangements, e.g. adhesives, sealants
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Manufacturing & Machinery (AREA)
  • Epoxy Resins (AREA)
  • Laminated Bodies (AREA)
  • Adhesive Tapes (AREA)
  • Sealing Material Composition (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Thermotherapy And Cooling Therapy Devices (AREA)
  • Packages (AREA)
  • Electroluminescent Light Sources (AREA)
  • Seal Device For Vehicle (AREA)
  • Containers And Plastic Fillers For Packaging (AREA)
  • Closing Of Containers (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

The present invention provides an adhesive sheet for sealing a device, which has a first release film, a second release film, and an adhesive layer sandwiched between the first release film and the second release film, and which satisfies all of the requirements regarding the components contained in the adhesive layer, the requirements regarding the storage elastic modulus of the adhesive layer, and the requirements regarding the release force of the release film, and a method for manufacturing a device sealed body using the same. When the adhesive sheet for sealing equipment of the present invention is used, the release film can be peeled off without breaking the adhesive layer.

Description

Adhesive sheet for sealing equipment and method for manufacturing sealing equipment
Technical Field
The present invention relates to an adhesive sheet for sealing a device, which has two release films and an adhesive layer sandwiched between these release films, and a method for manufacturing a device sealed body using the adhesive sheet for sealing a device.
Background
In recent years, an organic EL element has attracted attention as a light-emitting element capable of performing high-luminance light emission by low-voltage direct current driving.
However, the organic EL element has a problem that light emission characteristics such as light emission luminance, light emission efficiency, light emission uniformity, and the like are liable to be degraded with the passage of time.
As a cause of the problem of the deterioration of the light emission characteristics, it is considered that oxygen, moisture, and the like intrude into the inside of the organic EL element to deteriorate the electrode and the organic layer. Accordingly, it has been proposed to solve this problem by forming a sealing material using an adhesive layer or an adhesive layer having excellent moisture barrier properties.
For example, patent document 1 describes a sheet-like sealing material containing a specific epoxy resin, a specific alicyclic epoxy compound, a thermal cationic polymerization initiator, a photo cationic polymerization initiator, and a specific sensitizer.
The sealing material formed using the sheet-like sealing material described in patent document 1 has low oxygen permeability and moisture permeability and good sealing performance.
Prior art literature
Patent literature
Patent document 1: japanese patent application laid-open No. 2018-95679.
Disclosure of Invention
Problems to be solved by the invention
However, as in patent document 1, it is known that: in the case of forming the sealing material using the adhesive layer, a new problem may occur.
That is, the adhesive layer is usually manufactured and stored in a state sandwiched between two release films, and the release films are peeled off and removed when in use, but the first release film may not be peeled off and the adhesive layer may be broken.
The present invention has been made to solve the above-described problems, and an object of the present invention is to provide an adhesive sheet for sealing a device, which has two release films and an adhesive layer sandwiched between these release films, and which can peel the release films without breaking the adhesive layer, and a method for manufacturing a device sealed body using the adhesive sheet for sealing a device.
Means for solving the problems
The present inventors have made intensive studies with respect to an adhesive sheet for sealing a device, which has two release films and an adhesive layer sandwiched between these release films, the adhesive layer containing a compound having a cyclic ether group, in order to solve the above-mentioned problems.
The result shows that: the present invention has been accomplished by satisfying both the requirements regarding the storage elastic modulus of the adhesive layer at 23 ℃ and the requirements regarding the peeling force of the two release films, and by obtaining an adhesive sheet for sealing a device which can peel the release films without breaking the adhesive layer.
Thus, according to the present invention, the following adhesive sheet for sealing equipment [ 1 ] to [ 9 ] and the method for producing the sealing body for equipment [ 10 ] can be provided.
The adhesive sheet for sealing a device, which has a first release film, a second release film, and an adhesive layer sandwiched between the first release film and the second release film, satisfies all of the following requirements (I) to (III).
Essential condition (I): the adhesive layer is a layer containing 1 or 2 or more kinds of compounds having a cyclic ether group.
Essential condition (II): the adhesive layer has a storage elastic modulus at 23 ℃ of 5.0X10 5 Pa or more and 3.0X10 7 Pa or below.
Essential condition (III): the device sealing adhesive sheet satisfies the following formula (1) with the value of the peel force between the first peel film and the adhesive layer being represented by x (mN/50 mm) and the value of the peel force between the second peel film and the adhesive layer being represented by y (mN/50 mm).
[ mathematics ]]
x-y≥20 (1)。
The adhesive sheet for sealing a device according to [ 2 ], wherein at least 1 of the above-mentioned compounds having a cyclic ether group is a compound which is liquid at 25 ℃.
The adhesive sheet for sealing a device according to [ 3 ], wherein the content of the compound having a cyclic ether group, which is liquid at 25 ℃, is 53 mass% or more with respect to the entire adhesive layer.
The adhesive sheet for sealing a device according to any one of [ 1 ] to [ 3 ], wherein the adhesive layer is a layer further containing a thermal cationic polymerization initiator.
The adhesive sheet for sealing a device according to [ 5 ], wherein at least 1 of the above-mentioned compounds having a cyclic ether group is a compound having a glycidyl ether group.
The adhesive sheet for sealing a device according to any one of [ 1 ] to [ 5 ], wherein the adhesive layer is a layer further containing an adhesive resin.
The adhesive sheet for sealing a device according to [ 7 ], wherein the adhesive resin has a glass transition temperature of 90℃or higher.
The adhesive sheet for sealing a device according to any one of [ 1 ] to [ 7 ], wherein the layer obtained by curing the adhesive layer has a storage elastic modulus at 90℃of 1X 10 8 Pa or more.
The adhesive sheet for sealing equipment according to any one of [ 1 ] to [ 8 ], wherein the value x of the peel force between the first peel film and the adhesive layer is 30 to 200mN/50mm.
The method of manufacturing a device sealing body, comprising: a step of peeling the second peeling film from the adhesive sheet for sealing equipment according to any one of [ 1 ] to [ 9 ]; and adhering the exposed adhesive layer to the object to be sealed or the substrate at a temperature of 20-30 ℃.
Effects of the invention
According to the present invention, there is provided an adhesive sheet for sealing a device, which comprises two release films and an adhesive layer sandwiched between these release films, and which can peel off the release films without breaking the adhesive layer; and a method for manufacturing a device sealing body using the device sealing adhesive sheet.
Detailed Description
The adhesive sheet for sealing a device of the present invention is an adhesive sheet for sealing a device, which has a first release film, a second release film, and an adhesive layer sandwiched between the first release film and the second release film, and satisfies all of the above-described requirements (I), (II), and (III).
In the present invention, the "first release film" refers to a release film having a high release force from among the two release films, and the "second release film" refers to a release film having a low release force from among the two release films.
The "adhesive layer" is a layer obtained by coating a curable adhesive, and is a layer having curability, adhesiveness, and adhesiveness. That is, the "adhesive layer" is a layer in an uncured state.
In the present specification, the "layer obtained by curing the adhesive layer" may be referred to as an "adhesive cured product layer". The adhesive cured layer is used as a sealing material.
In the present invention, "curing" means that the cohesive force and the energy storage elastic modulus of the layer become high by the reaction of the cyclic ether group contained in the adhesive layer.
[ adhesive layer ]
(Compound having a cyclic ether group)
The adhesive layer contains 1 or 2 or more kinds of compounds having a cyclic ether group (hereinafter, sometimes referred to as "cyclic ether compounds (a)").
By curing the adhesive layer containing the cyclic ether compound (a), a sealing material having high adhesive strength and excellent water vapor barrier property can be formed.
The cyclic ether compound (a) is a compound having at least 1, preferably 2 or more cyclic ether groups in the molecule. In the present invention, the phenoxy resin described later is not included in the cyclic ether compound (a).
The molecular weight of the cyclic ether compound (A) is usually 100 to 5,000, preferably 200 to 3,000.
The cyclic ether equivalent of the cyclic ether compound (A) is preferably 50 to 1000g/eq, more preferably 100 to 800g/eq.
By curing the adhesive layer containing the cyclic ether compound (a) having the cyclic ether equivalent in the above range, a sealing material having higher adhesive strength and more excellent moisture barrier property can be formed more efficiently.
The cyclic ether equivalent in the present invention means a value obtained by dividing the molecular weight by the number of cyclic ether groups.
Examples of the cyclic ether group include an oxirane group (epoxy group), an oxetanyl group (oxetanyl group), a tetrahydrofuranyl group, and a tetrahydropyranyl group. Among these, the cyclic ether group is preferably an ethylene oxide group or an oxetanyl group, and more preferably an ethylene oxide group, from the viewpoint of being able to form a sealing material having higher adhesive strength.
For the same reason, the cyclic ether compound (a) preferably has 2 or more oxirane groups or oxetane groups in the molecule, and more preferably has 2 or more oxirane groups in the molecule.
Examples of the compound having an oxirane group in a molecule include aliphatic epoxy compounds (excluding alicyclic epoxy compounds), aromatic epoxy compounds, and alicyclic epoxy compounds.
Examples of the aliphatic epoxy compound include monofunctional epoxy compounds such as glycidyl ethers of aliphatic alcohols and glycidyl esters of alkyl carboxylic acids;
polyfunctional epoxy compounds such as polyglycidyl ethers of aliphatic polyols or alkylene oxide adducts thereof and polyglycidyl esters of aliphatic long-chain polybasic acids.
Representative examples of the aliphatic epoxy compounds include alkenyl glycidyl ethers such as allyl glycidyl ether; alkyl glycidyl ethers such as butyl glycidyl ether, 2-ethylhexyl glycidyl ether, and C12-13 mixed alkyl glycidyl ether; glycidyl ethers of polyhydric alcohols such as 1, 4-butanediol diglycidyl ether, neopentyl glycol diglycidyl ether, triglycidyl ether of glycerol, triglycidyl ether of trimethylolpropane, tetraglycidyl ether of sorbitol, hexaglycidyl ether of dipentaerythritol, diglycidyl ether of polyethylene glycol, diglycidyl ether of polypropylene glycol, and dicyclopentadiendimethanol diglycidyl ether; polyglycidyl etherate of polyether polyol obtained by adding 1 or more than 2 alkylene oxides to aliphatic polyol such as propylene glycol, trimethylolpropane, glycerol, etc.; diglycidyl esters of aliphatic long chain dibasic acids; monoglycidyl ethers of aliphatic higher alcohols, glycidyl esters of higher fatty acids, epoxidized soybean oil, octyl epoxy stearate, butyl epoxy stearate, epoxidized polybutadiene, and the like.
Further, as the aliphatic epoxy compound, a commercially available product can be used. As a commercial product, it is possible to obtain, examples of the compounds include dud (EX-121, dud (コ)) EX-171, dud (コ) EX-192, dud (コ) EX-211, dud (コ) EX-212, dud (コ) EX-313, dud (EX-314, dud (コ) EX-321, dud (コ) EX-411, dud (EX- コ) EX-421, dud (EX-512, dud (EX- コ) EX-521, dud (EX-611, dud (EX-612), dud (EX-614) and dud (EX-612), dud (EX- コ) EX-614, dud (EX-612), dud (EX-421), dud (EX-512, dud (EX- コ) and dud (EX-521); the term "dujiu" is used to include dujiu コ EX-622, dujiu コ EX-810, dujiu コ EX-811, dujiu コ EX-850, dujiu コ EX-851, dujiu コ EX-821, dujiu コ EX-830, dujiu コ EX-832, dujiu [ i ] EX-830, dujiu [ i ] コ ] EX-832; the term "Diu" as used herein means "Diu" such as Diu's コ EX-841, diu's コ EX-861, diu's コ EX-911, diu's コ EX-941, diu's コ EX-920, diu's コ EX-931 (the term "Diu's wax, the term" Diu's wax "is used herein);
the parts of the components are parts M-1230, 40E, 100E, 200E, 400E, 70P, 200P, 400P, 1500NP, 1600 MF 80MF and 100MF (the parts are manufactured by co-company chemical company);
A sheath-503 a rare ED-503G the metal sheath ED-506 and the metal sheath ED-523T (the above is manufactured by ADEKA company).
Examples of the aromatic epoxy compound include phenol having at least 1 aromatic ring such as phenol, cresol and butylphenol, and mono/polyglycidyl etherate of alkylene oxide adduct thereof; epoxy compounds having aromatic heterocyclic rings, and the like.
Representative examples of the aromatic epoxy compounds include glycidyl ethers of bisphenol a, bisphenol F, and compounds obtained by further adding alkylene oxide thereto, and epoxy novolac resins;
mono/polyglycidyl etherate of aromatic compounds having 2 or more phenolic hydroxyl groups such as resorcinol, hydroquinone and catechol;
glycidyl ethers of aromatic compounds having at least 2 alcoholic hydroxyl groups such as phenyldimethanol, phenyldiethanol and phenyldibutyl alcohol;
glycidyl esters of polybasic acid aromatic compounds having 2 or more carboxylic acids such as phthalic acid, terephthalic acid, and trimellitic acid, glycidyl esters of benzoic acid, and epoxides of ethylene oxide or divinylbenzene;
Epoxy compounds having a triazine skeleton such as 2,4, 6-tris (glycidyletheroxy) -1,3, 5-triazine, and the like.
Further, as the aromatic epoxy compound, a commercially available product can be used. As a commercial product, it is possible to obtain, examples of the components include dupont EX-146, dug コ, dug コ, EX-201, dug コ, dug EX-203, dug コ, dug EX-711, dug コ, dug EX-721, dug コ, EX-1020, dug コ, dug EX-1030, dug EX-1040, dug コ, EX-1050, dug EX-1051, dug EX-1010, dug コ, dug EX- コ, dug EX-1011, dug コ (the above is dug super-system, the above is manufactured by the company of the city of the power plant);
a pair of spindle PG-100, a pair of spindle PG-200, a pair of spindle EG-210, a pair of spindle EG-250 (the above are manufactured by the company of osaka, inc);
HP4032 and HP4032D, HP4700 (the above are manufactured by DIC Co.);
ESN-475V (above is a food, manufactured by Miquel company);
JER (original コ) YX8800 (mitsubishi, supra);
a case-wound G-0105SA, a case-wound G-0130SP (the above is manufactured by daily oil corporation);
to, and p, p N-665, p-N HP-7200 (the above is made by DIC);
EOCN-1020, EOCN-102S, EOCN-103S, EOCN-104S, XD-1000, NC-3000, EPPN-501H, EPPN-501HY, EPPN-502H, NC-7000L (manufactured by Japanese chemical Co., ltd.);
the components of the utility model include a dipterone EP-4000, a dipterone EP-4005, a dipterone EP-4100 ideas EP-4901 (manufactured by ADEKA corporation, above);
TECHMORE VG-3101L (from the above, tek corporation);
TEPIC-FL, TEPIC-PAS, TEPIC-UC (the above are manufactured by daily chemical company), and the like.
The alicyclic epoxy compound includes: polyglycidyl etherate of polyhydric alcohol having at least 1 alicyclic structure; or a compound containing cyclohexene oxide or cyclopentane which is obtained by epoxidizing a compound containing cyclohexene ring or cyclopentene ring with an oxidizing agent.
Representative examples of the alicyclic epoxy compounds include hydrogenated bisphenol A diglycidyl ether, 3, 4-epoxycyclohexylmethyl-3, 4-epoxycyclohexane carboxylate, 3, 4-epoxy-1-methylcyclohexyl-3, 4-epoxycyclohexane carboxylate, 6-methyl-3, 4-epoxycyclohexylmethyl-6-methyl-3, 4-epoxycyclohexane carboxylate, 3, 4-epoxy-3-methylcyclohexylmethyl-3, 4-epoxy-3-methylcyclohexane carboxylate, 3, 4-epoxy-5-methylcyclohexylmethyl-3, 4-epoxy-5-methylcyclohexane carboxylate, bis (3, 4-epoxycyclohexylmethyl) adipate, 3, 4-epoxy-6-methylcyclohexane carboxylate, methylenebis (3, 4-epoxycyclohexane), propane-2, 2-diyl-bis (3, 4-epoxycyclohexane), 2-bis (3, 4-epoxycyclohexane) propane, dicyclopentadiene di-3, 4-epoxycyclohexane carboxylate, ethylene bis (3, 4-epoxycyclohexane carboxylate), ethylene oxide, and 2-diethylcyclohexane oxide.
Further, as the alicyclic epoxy compound, a commercially available compound can be used. Examples of the commercial products include a substrate 2021P, a substrate 2081, a substrate 2000, a substrate 3000 (manufactured by the company named as the above); and PEGyro 4000 (manufactured by co-Rong chemical Co., ltd.); YX8000, YX8034 (mitsubishi corporation); the components of the umbilical cord are umbilical EP-4088S, umbilical cord EP-4088L and iderobar EP-4080E (manufactured by ADEKA corporation, above).
Further, as the compound having an oxirane group in a molecule, an epoxy compound having both an alicyclic structure and an aromatic ring in one molecule can be mentioned. Examples of such a compound include, for example, an d-fin HP-7200 (manufactured by DIC corporation).
Among these, from the viewpoint of lowering the dielectric constant of the adhesive cured product layer, the compound having an oxirane group is preferably an alicyclic epoxy resin.
In the case of using a thermal cationic polymerization initiator as a curing catalyst to be described later, the compound having an ethylene oxide group is preferably a compound having a glycidyl ether group. The glycidyl ether groups undergo cationic polymerization relatively gently. Therefore, in the case where there is a step of heating the composition containing the components constituting the adhesive layer (for example, a step of heating to 90 ℃ or higher) in the step of producing the adhesive layer, it is difficult to carry out the polymerization reaction of the glycidyl ether group, and the storage elastic modulus of the adhesive layer at 23 ℃ is easily maintained low. The content of the compound having a glycidyl ether group is preferably 70% by mass or more, and more preferably 90% by mass or more, based on the entire compound having a cyclic ether group.
Examples of the compound having an oxetanyl group in the molecule include difunctional aliphatic oxetane compounds such as 3, 7-bis (3-oxetanyl) -5-oxononane, 1, 4-bis [ (3-ethyl-3-oxetylmethoxy) methyl ] benzene, 1, 2-bis [ (3-ethyl-3-oxetylmethoxy) methyl ] ethane, 1, 3-bis [ (3-ethyl-3-oxetylmethoxy) methyl ] propane, ethylene glycol bis (3-ethyl-3-oxetylmethyl) ether, triethylene glycol bis (3-ethyl-3-oxetylmethyl) ether, tetraethylene glycol bis (3-ethyl-3-oxetylmethyl) ether, 1, 4-bis (3-ethyl-3-oxetylmethoxy) butane, and 1, 6-bis (3-ethyl-3-oxetylmethoxy) hexane; monofunctional oxetane compounds such as 3-ethyl-3- [ (phenoxy) methyl ] oxetane, 3-ethyl-3- (hexyloxymethyl) oxetane, 3-ethyl-3- (2-ethylhexyloxymethyl) oxetane, 3-ethyl-3- (hydroxymethyl) oxetane, and 3-ethyl-3- (chloromethyl) oxetane.
As the compound having an oxetanyl group in the molecule, a commercially available product can be used. Examples of the commercial products include 2-hydroxyethyl vinyl ether, diethylene glycol monovinyl ether, and 4-hydroxybutyl vinyl ether (the above are manufactured by Wash petrochemicals Co., ltd.);
Fall-on, which is an element of the group consisting of OXT-121, OXT-221, EXOH, POX, OXA, OXT-101, and Fall-on OXT-211, OXT-212 (manufactured above by east Asia Synthesis Co.);
and (d) can be コ (OXBP, OXTP, manufactured by yu zhi co., ltd.).
These cyclic ether compounds (A) may be used singly or in combination of 1 or more than 2.
The content of the cyclic ether compound (a) in the adhesive layer (when the adhesive layer contains 2 or more kinds of cyclic ether compounds (a), the total amount thereof is preferably 45 to 90% by mass, more preferably 50 to 85% by mass, and still more preferably 60 to 80% by mass, relative to the entire adhesive layer.
By setting the content of the cyclic ether compound (a) to the above range, an adhesive cured product layer having a high energy storage elastic modulus at 90 ℃ can be easily obtained.
The at least 1 cyclic ether compound (a) in the adhesive layer is preferably a compound that is liquid at 25 ℃ (cyclic ether compound (AL) that is liquid at 25 ℃). Here, the liquid means one of the aggregate states of the substances, which is a state having a substantially constant volume but not having a fixed shape.
By using the cyclic ether compound (AL) which is liquid at 25 ℃, it is possible to suppress the storage elastic modulus of the adhesive layer from becoming excessively high at 23 ℃. Therefore, an adhesive layer having a sufficient adhesive force in the vicinity of room temperature (20 to 30 ℃ C. Or lower) can be easily obtained.
The cyclic ether equivalent of the cyclic ether compound (AL) which is liquid at 25 ℃ is preferably 150 to 1000g/eq, more preferably 240 to 900g/eq, from the viewpoint of adjusting the storage elastic modulus of the adhesive layer at 23 ℃.
The content of the cyclic ether compound (AL) in the adhesive layer, which is liquid at 25 ℃ (when the adhesive layer contains 2 or more kinds of compounds, the total amount of these compounds is preferably 53% by mass or more, more preferably 53 to 80% by mass, and still more preferably 54 to 65% by mass, based on the entire adhesive layer. By setting the content of the cyclic ether compound (AL) which is liquid at 25 ℃ to 53 mass% or more relative to the entire adhesive layer, an adhesive layer having sufficient adhesive force in the vicinity of room temperature can be easily obtained. In addition, an adhesive cured product layer having a high storage elastic modulus at 90℃can be easily obtained. Further, by setting the content of the cyclic ether compound (AL) which is liquid at 25 ℃ to 80 mass% or less relative to the entire adhesive layer, the storage elastic modulus of the adhesive layer at 23 ℃ is easily increased.
(Binder resin)
The adhesive layer may contain an adhesive resin (B). The adhesive layer containing the adhesive resin is excellent in shape retention and handling properties.
The weight average molecular weight (Mw) of the binder resin (B) is not particularly limited, but is preferably 10,000 or more, more preferably 10,000 to 150,000, and still more preferably 10,000 to 100,000, from the viewpoint of more excellent compatibility with the cyclic ether compound (a) and further excellent shape retention.
The weight average molecular weight (Mw) of the binder resin can be determined by Gel Permeation Chromatography (GPC) using Tetrahydrofuran (THF) as a solvent and in the form of standard polystyrene conversion values.
When the adhesive layer contains the adhesive resin (B), the content of the adhesive resin (when the adhesive resin contains 2 or more adhesive resins, the total amount thereof) is preferably 5 to 50% by mass, more preferably 10 to 45% by mass, relative to the entire adhesive layer.
By setting the content of the binder resin (B) within the above range, an adhesive layer excellent in shape retention and having sufficient adhesive force can be easily obtained.
As will be described later, the storage elastic modulus of the adhesive cured product layer at 90℃was 1X 10 8 If Pa or more, the binder resin (B) is preferably a resin having a glass transition temperature of 90 ℃ or more, since the storage elastic modulus of the cured adhesive layer tends to increase at 90 ℃. Examples of the resin having a glass transition temperature of 90℃or higher includeA part of phenoxy resin, polyimide resin, polyamideimide resin, polyvinyl butyral resin, polycarbonate resin, and the like. Examples of the resin having a glass transition temperature of less than 90℃include acrylic resins, urethane resins, and olefin resins.
These resins may be used singly or in combination of 1 or more than 2.
The binder resin (B) is preferably at least one selected from the group consisting of phenoxy resins and modified olefin resins, and is preferably phenoxy resins from the viewpoint of improving the storage elastic modulus of the adhesive cured product layer at 90 ℃.
The phenoxy resin is generally a high molecular weight epoxy resin, and is a resin having a degree of polymerization of about 100 or more.
The weight average molecular weight (Mw) of the phenoxy resin used in the present invention is preferably 10,000 to 150,000, more preferably 10,000 to 100,000. The weight average molecular weight (Mw) of the phenoxy resin can be determined as a standard polystyrene equivalent by Gel Permeation Chromatography (GPC) using Tetrahydrofuran (THF) as a solvent.
The phenoxy resin which corresponds to such a high molecular weight epoxy resin is excellent in heat distortion resistance.
The phenoxy resin used in the present invention preferably has an epoxy equivalent of 5,000 or more, more preferably 7,000 or more. The value of the epoxy equivalent can be measured in accordance with JIS K7236.
Examples of the phenoxy resin used in the present invention include bisphenol a type, bisphenol F type, bisphenol S type phenoxy resin, bisphenol a type and bisphenol F type copolymer type phenoxy resin, distillate thereof, naphthalene type phenoxy resin, novolak type phenoxy resin, biphenyl type phenoxy resin, cyclopentadiene type phenoxy resin, and the like.
These phenoxy resins may be used singly or in combination of 1 or more than 2.
The phenoxy resin can be obtained by a method of reacting a difunctional phenol with an epihalohydrin to a high molecular weight or by polyaddition of a difunctional epoxy resin with a difunctional phenol.
For example, the compound can be obtained by reacting a difunctional phenol with an epihalohydrin in the presence of an alkali metal hydroxide and in an inert solvent at a temperature of 40 to 120 ℃. Further, the resin can be obtained by heating a difunctional epoxy resin and a difunctional phenol to 50 to 200 ℃ in the presence of a catalyst such as an alkali metal compound, an organic phosphorus compound, or a cyclic amine compound in an organic solvent such as an amide solvent, an ether solvent, a ketone solvent, a lactone solvent, or an alcohol solvent having a boiling point of 120 ℃ or higher, at a concentration of 50% by weight or less of the solid content of the reaction, and causing the polyaddition reaction.
The difunctional phenols are not particularly limited as long as they are compounds having 2 phenolic hydroxyl groups. Examples thereof include monocyclic difunctional phenols such as hydroquinone, 2-bromohydroquinone, resorcinol and catechol; bisphenols such as bisphenol a, bisphenol F, bisphenol AD, bisphenol S, etc.; dihydroxybiphenyls such as 4,4' -dihydroxybiphenyl; dihydroxyphenyl ethers such as bis (4-hydroxyphenyl) ether; a linear alkyl group, a branched alkyl group, an aryl group, a hydroxymethyl group, an allyl group, a cyclic aliphatic group, a halogen (tetrabromobisphenol a, etc.), a nitro group, etc., are introduced into the aromatic ring of the phenol skeleton; and polycyclic difunctional phenols obtained by introducing a linear alkyl group, a branched alkyl group, an allyl group, a substituted allyl group, a cyclic aliphatic group, an alkoxycarbonyl group, or the like into a carbon atom in the center of these bisphenol skeletons.
Examples of the epihalohydrin include epichlorohydrin, epibromohydrin, and iodohydrin.
In the present invention, a commercially available resin may be used as the phenoxy resin. For example, trade names manufactured by mitsubishi chemical company are listed: YX7200 (glass transition temperature: 150 ℃), YX6954 (phenoxy resin having bisphenol acetophenone skeleton, glass transition temperature: 130 ℃), YL7553, YL6794, YL7213, YL7290, YL7482, YX8100 (phenoxy resin having bisphenol S skeleton), trade name manufactured by eastern chemical company: FX280, FX293S (phenoxy resin containing fluorene skeleton), mitsubishi chemical company trade name: jER1256, jER4250 (glass transition temperature: less than 85 ℃), jER4275 (glass transition temperature: 75 ℃), and trade names of Nitro chemical and temperature company: YP-50 (glass transition temperature: 84 ℃ C.), YP-50S (all of which are phenoxy resins containing bisphenol A skeleton), YP-70 (bisphenol A skeleton/bisphenol F skeleton copolymerization phenoxy resins, glass transition temperature: less than 85 ℃ C.), ZX-1356-2 (glass transition temperature: 72 ℃ C.), and the like. The glass transition temperature is shown for a substance whose glass transition temperature is clear.
The modified olefin resin is an olefin resin having functional groups introduced therein, which is obtained by modifying an olefin resin as a precursor with a modifier.
The olefinic resin means a polymer containing a repeating unit derived from an olefinic monomer. The olefinic resin may be a polymer containing only repeating units derived from an olefinic monomer, or may be a polymer containing repeating units derived from an olefinic monomer and repeating units derived from a monomer copolymerizable with the olefinic monomer.
The olefin monomer is preferably an α -olefin having 2 to 8 carbon atoms, more preferably ethylene, propylene, 1-butene, isobutylene or 1-hexene, and still more preferably ethylene or propylene. These olefin monomers may be used singly or in combination of 1 or more than 2.
Examples of the monomer copolymerizable with the olefin monomer include vinyl acetate, (meth) acrylate, and styrene. Here, "(meth) acrylic acid" means acrylic acid or methacrylic acid (the same applies hereinafter).
The monomer copolymerizable with these olefin monomers may be used alone or in combination of 1 or more than 2.
Examples of the olefin-based resin include Very Low Density Polyethylene (VLDPE), low Density Polyethylene (LDPE), medium Density Polyethylene (MDPE), high Density Polyethylene (HDPE), linear low density polyethylene, polypropylene (PP), ethylene-propylene copolymer, olefin-based elastomer (TPO), ethylene-vinyl acetate copolymer (EVA), ethylene- (meth) acrylic acid copolymer, and ethylene- (meth) acrylic acid ester copolymer.
The modifier used in the modification treatment of the olefin resin is a compound having a functional group in the molecule.
Examples of the functional group include a carboxyl group, a carboxylic anhydride group, a carboxylic ester group, a hydroxyl group, an epoxy group, an amide group, an ammonium group, a nitrile group, an amino group, an imide group, an isocyanate group, an acetyl group, a thiol group, an ether group, a thioether group, a sulfo group, a phosphono group, a nitro group, a urethane group, an alkoxysilyl group, a silanol group, and a halogen atom. The compound having a functional group may have 2 or more functional groups in the molecule.
The modified olefin resin is preferably an acid-modified olefin resin.
The acid-modified olefin resin is a resin obtained by graft-modifying an olefin resin with an acid or an acid anhydride. Examples thereof include resins obtained by reacting an olefin resin with an unsaturated carboxylic acid or an unsaturated carboxylic anhydride (hereinafter, sometimes referred to as "unsaturated carboxylic acid or the like") to introduce (graft-modify) a carboxyl group or a carboxylic anhydride group.
Examples of the unsaturated carboxylic acid that reacts with the olefin resin include unsaturated carboxylic acids such as maleic acid, fumaric acid, itaconic acid, citraconic acid, glutaconic acid, tetrahydrophthalic acid, aconitic acid, and the like; unsaturated carboxylic acid anhydrides such as maleic anhydride, itaconic anhydride, glutaconic anhydride, citraconic anhydride, aconitic anhydride, norbornene dicarboxylic anhydride, tetrahydrophthalic anhydride, and the like.
They may be used alone or in combination of 1 or more than 2. Among these, maleic anhydride is preferable in terms of easy availability of a sealing material having higher adhesive strength.
The amount of the unsaturated carboxylic acid or the like to be reacted with the olefin resin is preferably 0.1 to 5 parts by mass, more preferably 0.2 to 3 parts by mass, and still more preferably 0.2 to 1 part by mass relative to 100 parts by mass of the olefin resin. By curing the adhesive layer containing the acid-modified olefin resin obtained in this way, a sealing material having higher adhesive strength can be formed.
The method of introducing the unsaturated carboxylic acid unit or the unsaturated carboxylic acid anhydride unit into the olefin resin is not particularly limited. For example, the following methods are mentioned: a method in which an olefin resin and an unsaturated carboxylic acid or the like are heated and melted to a temperature equal to or higher than the melting point of the olefin resin in the presence of a radical generator such as an organic peroxide or an azonitrile; alternatively, a method in which an olefin resin, an unsaturated carboxylic acid or the like is dissolved in an organic solvent, and then heated and stirred in the presence of a radical generator to react with the resulting mixture, and a method in which an unsaturated carboxylic acid or the like is graft-copolymerized with an olefin resin.
As the acid-modified olefin resin, commercially available ones can be used. Examples of the commercial products include a company (registered trademark), a company (BondyRam), a company (registered trademark), a company (ARKEMA), a company (registered trademark), and a company (registered trademark).
The modified olefin resin preferably has a weight average molecular weight (Mw) of 10,000 to 150,000, more preferably 30,000 to 100,000.
The weight average molecular weight (Mw) of the modified olefin-based resin can be determined as a standard polystyrene conversion value by Gel Permeation Chromatography (GPC) using Tetrahydrofuran (THF) as a solvent.
(curing catalyst)
The adhesive layer may contain a curing catalyst. The curing catalyst is used for promoting the reaction of the cyclic ether group in the cyclic ether compound (a).
The curing catalyst may be an anionic polymerization initiator or a cationic polymerization initiator.
The cationic polymerization initiator is preferable from the viewpoint of performing the curing reaction in a short time and improving the storage stability of the adhesive layer.
Examples of the anionic polymerization initiator include imidazole-based curing catalysts such as 2-methylimidazole, 2-phenylimidazole, 2-undecylimidazole, 2-heptadecylimidazole, 2-ethyl-4-methylimidazole, 2-phenyl-4-methyl-5-hydroxymethylimidazole, and 2-phenyl-4, 5-dihydroxymethylimidazole.
Examples of the cationic polymerization initiator include a thermal cationic polymerization initiator and a photo cationic polymerization initiator, and the thermal cationic polymerization initiator is preferable from the viewpoint of being usable even when the adhesive layer is difficult to be irradiated with light in the production process of the device sealing body and from the viewpoint of versatility of the heat curing device.
The thermal cationic polymerization initiator is a compound capable of generating a cationic species that initiates polymerization by heating.
Examples of the thermal cationic polymerization initiator include sulfonium salts, quaternary ammonium salts, phosphonium salts, diazonium salts, and iodonium salts. Among these, sulfonium salts are preferred from the viewpoints of easy availability, easy availability of a sealing material excellent in adhesion and transparency, and the like.
Examples of sulfonium salts include triphenylsulfonium tetrafluoroborate, triphenylsulfonium hexafluoroantimonate, triphenylsulfonium hexafluoroarsonate, tris (4-methoxyphenyl) sulfonium hexafluoroarsonate, and diphenyl (4-phenylsulfanylphenyl) sulfonium hexafluoroarsonate.
Further, as the sulfonium salt, commercially available ones can be used. As a commercial product, it is possible to obtain, examples of the method include a front end SP-150, a front end SP-170, a front end CP-66, a front end CP-77 (manufactured by ADEKA corporation, above), a front end SI-60L, a front end SI-80L, a front end SI-100L (manufactured by Sanxinhu corporation, above), a CYRACURE UVI-6974, a CYRACURE UVI-6990 (manufactured by primary corporation, above), a front end SI-60L, a front end SI-80L, a front end SI-100L (manufactured by Sanxinhu corporation, above), a CYRACURE UVI-6990 (manufactured by primary corporation, above), a front end SI-6990; UVI-508, UVI-509 (made by the company of the back of the back to the back to the book back and the book back CD-1010, CD-1011 (from the company of.
Specific examples of the quaternary ammonium salt include tetrabutylammonium tetrafluoroborate, tetrabutylammonium hexafluorophosphate, tetrabutylammonium hydrogensulfate, tetraethylammonium tetrafluoroborate, tetraethylammonium p-toluenesulfonate, N-dimethyl-N-benzylaniline hexafluoroantimonate, N-dimethyl-N-benzylaniline tetrafluoroborate, N, N-dimethyl-N-benzylpyridinium hexafluoroantimonate, N-diethyl-N-benzyltriflate, N-dimethyl-N- (4-methoxybenzyl) pyridinium hexafluoroantimonate, N-diethyl-N- (4-methoxybenzyl) toluidine hexafluoroantimonate, and the like. Examples of the phosphonium salt include ethyltriphenylphosphonium hexafluoroantimonate and tetrabutylphosphonium hexafluoroantimonate.
Examples of diazonium salts include AMERICURE (manufactured by the company falcan, tikun) and ULTRASET (manufactured by the company ADEKA).
Examples of the iodonium salts include diphenyliodonium hexafluoroarsenate, bis (4-chlorophenyl) iodonium hexafluoroarsenate, bis (4-bromophenyl) iodonium hexafluoroarsenate, and phenyl (4-methoxyphenyl) iodonium hexafluoroarsenate. In addition, as a commercial product, examples of the material include UV-9310C (manufactured by toshiba コ), photo operator 2074 (manufactured by low-level company), UVE series products (manufactured by low-level company, by the low-level company), FC series products (manufactured by the low-level company), and FC series products (manufactured by the low-level company, by the low-level company), and the like.
The photo-cationic polymerization initiator is a compound capable of generating a cationic species that initiates polymerization by light irradiation.
Examples of the photo-cation polymerization initiator include aromatic sulfonium salts, aromatic iodonium salts, aromatic diazonium salts, and thioxanthonium salts.
The aromatic sulfonium salt is a salt having an aromatic sulfonium as a cationic moiety. Further, as the anionic portion, there is BF 4 - 、PF 6 - 、SbF 6 - And (3) plasma anions.
Examples of the aromatic sulfonium salt include triphenylsulfonium hexafluorophosphate, triphenylsulfonium hexafluoroantimonate, diphenyl-4- (phenylthio) phenylsulfonium hexafluorophosphate, and diphenyl-4- (phenylthio) phenylsulfonium hexafluoroantimonate.
The aromatic iodonium salt is a salt having an aromatic iodonium as a cation moiety. The anion moiety may be the same as that of the aromatic sulfonium salt.
Examples of the aromatic iodonium salts include diphenyliodonium hexafluorophosphate, diphenyliodonium hexafluoroantimonate, diphenyliodonium tetrafluoroborate, diphenyliodonium tetrakis (pentafluorophenyl) borate, bis (dodecylphenyl) iodonium hexafluorophosphate, and 4-methylphenyl-4- (1-methylethyl) phenyliodonium hexafluorophosphate.
The aromatic diazonium salt is a salt having an aromatic diazonium as a cationic moiety. The anion moiety may be the same as that of the aromatic sulfonium salt.
Examples of the aromatic diazonium salt include phenyl diazonium hexafluorophosphate, phenyl diazonium hexafluoroantimonate, phenyl diazonium tetrafluoroborate, and phenyl diazonium tetrakis (pentafluorophenyl) borate.
Thioxanthonium salts are salts having thioxanthonium as the cationic moiety. The anion moiety may be the same as that of the aromatic sulfonium salt.
Examples of the thioxanthone onium salt include S-biphenyl-2-isopropylthioxanthone onium hexafluorophosphate and the like.
The adhesive layer may contain 1 kind of curing catalyst or 2 or more kinds.
When the adhesive layer contains a curing catalyst, the content of the curing catalyst (when the curing catalyst contains 2 or more types of curing catalysts, the total amount of these is not particularly limited, but is preferably 0.1 to 15 parts by mass, more preferably 1 to 10 parts by mass, based on 100 parts by mass of the cyclic ether compound (a).
(silane coupling agent)
The adhesive layer may contain a silane coupling agent. By curing the adhesive layer containing the silane coupling agent, a sealing material having more excellent wet heat durability can be formed.
As the silane coupling agent, a known silane coupling agent can be used. Among them, an organosilicon compound having at least 1 alkoxysilyl group in the molecule is preferable.
Examples of the silane coupling agent include silane coupling agents having a (meth) acryloyl group such as 3-methacryloxypropyl methyl dimethoxy silane, 3-methacryloxypropyl trimethoxy silane, 3-methacryloxypropyl methyl diethoxy silane, 3-methacryloxypropyl triethoxy silane, 3-acryloxypropyl trimethoxy silane, and 8-methacryloxyoctyl trimethoxy silane;
silane coupling agents having a vinyl group such as vinyltrimethoxysilane, vinyltriethoxysilane, dimethoxymethylvinylsilane, diethoxymethylvinylsilane, trichlorovinylsilane, vinyltris (2-methoxyethoxy) silane, and 6-octenyltrimethoxysilane;
silane coupling agents having an epoxy group, such as 2- (3, 4-epoxycyclohexyl) ethyltrimethoxysilane, 3-epoxypropoxypropyltrimethoxysilane, 3-epoxypropoxypropylmethyldiethoxysilane, 3-epoxypropoxypropyltriethoxysilane, 8-epoxypropoxyoctyltrimethoxysilane;
silane coupling agents having a styrene group such as p-styryl trimethoxysilane and p-styryl triethoxysilane;
Silane coupling agents having an amino group such as hydrochloride salts of N- (2-aminoethyl) -3-aminopropyl methyldimethoxy silane, N- (2-aminoethyl) -3-aminopropyl trimethoxy silane, N- (2-aminoethyl) -3-aminopropyl triethoxy silane, 3-aminopropyl trimethoxy silane, 3-triethoxysilyl-N- (1, 3-dimethyl, butylfork) propylamine, N-phenyl-3-aminopropyl trimethoxy silane, N- (vinylbenzyl) -2-aminoethyl-3-aminopropyl trimethoxy silane;
silane coupling agents having an ureido group such as 3-ureidopropyltrimethoxysilane and 3-ureidopropyltriethoxysilane;
silane coupling agents having halogen atoms such as 3-chloropropyl trimethoxysilane and 3-chloropropyl triethoxysilane;
mercapto silane coupling agents such as 3-mercaptopropyl methyl dimethoxy silane and 3-mercaptopropyl trimethoxy silane;
silane coupling agents having a thioether group, such as bis (trimethoxysilylpropyl) tetrasulfide and bis (triethoxysilylpropyl) tetrasulfide;
silane coupling agents having an isocyanate group such as 3-isocyanatopropyl trimethoxysilane and 3-isocyanatopropyl triethoxysilane;
Silane coupling agents having an allyl group, such as allyl trichlorosilane, allyl triethoxysilane, and allyl trimethoxysilane;
and silane coupling agents having a hydroxyl group such as 3-hydroxypropyl trimethoxysilane and 3-hydroxypropyl triethoxysilane.
Among these, from the viewpoint of improving the adhesion of the adhesive layer to the surface of the device to be sealed, a long-chain spacer type silane coupling agent having an alkyl group having 4 to 8 carbon atoms between an alkoxysilyl group and an organic group, such as 8-methacryloxy octyl trimethoxy silane, 6-octenyl trimethoxy silane, 8-glycidoxy octyl trimethoxy silane, and the like, is preferable.
These silane coupling agents may be used singly or in combination of 1 or more than 2.
When the adhesive layer contains a silane coupling agent, the content of the silane coupling agent (when the adhesive layer contains 2 or more silane coupling agents, the total amount of these agents) is preferably 0.01 to 5% by mass, more preferably 0.05 to 1% by mass, based on the entire adhesive layer.
The content of the silane coupling agent is preferably 0.01 to 10 parts by mass, more preferably 0.02 to 5 parts by mass, based on 100 parts by mass of the component (a).
By making the content of the silane coupling agent within the above range, a sealant excellent in wet heat durability can be more easily obtained.
(other Components)
The adhesive layer may contain other components within a range that does not hinder the effects of the present invention.
Examples of the other components include additives such as ultraviolet absorbers, antistatic agents, light stabilizers, antioxidants, resin stabilizers, fillers, pigments, extenders, softeners, and tackifiers.
They may be used alone or in combination of 1 or more than 2.
When the adhesive layer contains these additives, the content thereof can be appropriately determined according to the purpose.
(adhesive layer)
The shape, size, etc. of the adhesive layer are not particularly limited. The shape may be a short bar or a long bar. In the present specification, "long strip" refers to a shape having a length of 5 times or more, preferably 10 times or more, the width, and specifically to a film shape having a length of a degree that the film can be rolled into a roll and stored or transported. The upper limit of the ratio of the length to the width of the film is not particularly limited, and may be set to, for example, 100,000 times or less.
The thickness of the adhesive layer is usually 1 to 50. Mu.m, preferably 1 to 25. Mu.m, more preferably 5 to 25. Mu.m. An adhesive layer having a thickness within the above range can be suitably used as a forming material of the sealing material.
The thickness of the adhesive layer can be measured in accordance with JIS K7130 (1999) using a known thickness meter.
The adhesive layer may have a single-layer structure or a multilayer structure (a structure in which a plurality of adhesive layers are laminated).
The adhesive layer may be a layer having a uniform composition or a layer having a non-uniform composition (for example, in the adhesive layer having the above-described multilayer structure, two components are mixed with each other at the interface between the two adhesive layers to form a layer having a single-layer structure on appearance).
The adhesive layer had a storage elastic modulus at 23℃of 5.0X10 5 Pa or more, preferably 7.0X10 5 Pa or more. By making the storage elastic modulus of the adhesive layer at 23 ℃ 5.0X10 5 Pa or more, the release film can be peeled without breaking the adhesive layer.
Storage elastic modulus at 23℃is 5.0X10 5 The adhesive layer of Pa or more can be easily obtained by using, for example, a substance having a large cyclic ether equivalent as the cyclic ether compound (a). Further, by reducing the content of the cyclic ether compound (AL) which is liquid at 25 ℃ in the adhesive layer, the storage elastic modulus of the adhesive layer at 23 ℃ can be reduced. Further, even if a relatively rigid resin such as a phenoxy resin is used Even when the content of the cyclic ether compound (AL) which is liquid at 25 ℃ in the adhesive layer is large, it is easy to obtain a storage elastic modulus at 23 ℃ of 5.0×10 5 And an adhesive layer of Pa or more.
The adhesive layer had a storage elastic modulus at 23℃of 3.0X10 7 Pa or less, preferably 2.0X10 7 Pa or less, more preferably 1.5X10 7 Pa or below. Storage elastic modulus at 23℃is 3.0X10 7 The adhesive layer of Pa or less has a sufficient adhesive force at room temperature, and therefore has excellent adhesion suitability to an object to be sealed at room temperature.
Storage elastic modulus at 23℃is 3.0X10 7 The adhesive layer of Pa or less can be easily obtained by, for example, increasing the amount of the cyclic ether compound (AL) that is liquid at 25 ℃. In addition, as described above, when the adhesive layer contains a thermal cationic polymerization initiator, the cyclic ether compound (a) is a compound having a glycidyl ether group, whereby the storage elastic modulus of the adhesive layer at 23 ℃ is reduced and is easily made to be 3.0x10 7 Pa or below.
The storage elastic modulus of the adhesive layer can be measured using a known dynamic viscoelasticity measuring device.
Specifically, the measurement can be performed by the method described in examples.
The adhesive layer has curability. Specifically, the adhesive layer is subjected to a specific curing treatment, whereby the cyclic ether group in the cyclic ether compound (a) reacts, and the adhesive layer is cured to form an adhesive cured product layer.
The curing treatment includes a heating treatment, a light irradiation treatment, and the like. They may be appropriately determined according to the nature of the adhesive layer.
The storage modulus of the cured adhesive layer at 90℃is preferably 1X 10 8 Pa or more, more preferably 1×10 9 ~1×10 11 Pa. Storage elastic modulus at 90℃is 1X 10 8 The adhesive cured layer of Pa or more is excellent in sealability and therefore is more suitable as a sealing material. In addition, after the adhesive cured product layer is formed, the adhesive cured product layer is sealed for manufacturing equipmentIn the step of performing the step, the adhesive cured product layer is easily prevented from being broken or peeled off.
The storage elastic modulus of the adhesive cured product layer can be measured using a known dynamic viscoelasticity measuring device.
Specifically, the measurement can be performed by the method described in examples.
The adhesive cured layer has excellent adhesive strength. When 180 DEG peel test is performed at a temperature of 23 ℃ and a relative humidity of 50%, the adhesive strength of the cured adhesive layer is usually 1 to 20N/25mm, preferably 2.5 to 15N/25mm. The 180 ° peel test can be performed, for example, under the conditions of a temperature of 23 ℃ and a relative humidity of 50% according to the method for measuring the adhesive force described in JIS Z0237:2009.
When the adhesive sheet for sealing a device of the present invention is used for sealing a display or the like, the cured adhesive layer is preferably colorless and excellent in transparency. The total light transmittance of the adhesive cured product layer having a thickness of 20 μm is preferably 85% or more, more preferably 90% or more. The upper limit of the total light transmittance is not particularly limited, and is usually 95% or less.
The total light transmittance can be measured in accordance with JIS K7361-1:1997.
The water vapor transmission rate of the adhesive cured product layer is usually 0.1 to 200g seed m -2 ・day -1 Preferably 1 to 150g of seed m -2 ・day -1 。
The water vapor permeability can be measured using a known gas transmittance measuring device.
[ Release film ]
The adhesive sheet for sealing equipment of the present invention has a first release film and a second release film.
When the adhesive sheet for sealing equipment of the present invention is used, the release film is usually removed by peeling. At this time, since the peeling force of the second peeling film is lower, the second peeling film is peeled off earlier than the first peeling film.
In the following description, the "first release film" and the "second release film" are sometimes not distinguished, but abbreviated as "release film".
The release film functions as a support in the process of manufacturing the device sealing adhesive sheet, and functions as a protective sheet for the adhesive layer until the device sealing adhesive sheet is used.
As the release film, a conventionally known release film can be used. Examples of the release film include a release film having a release layer on a release film substrate. The release layer may be formed using a known release agent.
Examples of the base material for a release film include paper base materials such as cellophane, coated paper, and high-quality paper; laminated paper in which thermoplastic resin such as polyethylene is laminated on the paper base material; plastic films such as polyethylene terephthalate resin, polybutylene terephthalate resin, polyethylene naphthalate resin, polypropylene resin, and polyethylene resin.
Examples of the release agent include rubber-based elastomers such as silicone-based resins, olefin-based resins, isoprene-based resins, and butadiene-based resins, long-chain alkyl-based resins, alkyd-based resins, and fluorine-based resins.
The thickness of the release film is not particularly limited, and is usually about 20 to 250. Mu.m.
[ adhesive sheet for sealing Equipment ]
The adhesive sheet for sealing a device of the present invention comprises the first release film, the second release film, and the adhesive layer sandwiched between these release films.
The adhesive sheet for sealing a device of the present invention includes a three-layer structure of a first release film, an adhesive layer, and a second release film.
The method for producing the adhesive sheet for sealing a device of the present invention is not particularly limited. For example, an adhesive sheet for sealing a device can be produced by a casting method.
When the adhesive sheet for sealing a device is produced by the casting method, the production can be performed by, for example, the following method.
Two release films (release film (a) and release film (B)) each having a release layer and a coating liquid containing a component constituting an adhesive layer were prepared. The adhesive layer is formed by applying the coating liquid to the release layer surface of the release film (a) by a known method, and drying the obtained coating film. Next, the release film (B) is laminated on the adhesive layer so that the release layer surface of the release film (B) contacts the adhesive layer, whereby an adhesive sheet for sealing a device can be obtained.
When the components constituting the adhesive layer are diluted to prepare a coating liquid, examples of the solvent used for preparing the coating liquid include 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 n-pentane, n-hexane and n-heptane; alicyclic hydrocarbon solvents such as cyclopentane, cyclohexane and methylcyclohexane.
These solvents may be used singly or in combination of 1 or more than 2.
The content of the solvent may be appropriately determined in consideration of coatability and the like.
Examples of the coating method of the coating liquid include spin coating, spray coating, bar coating, knife coating, roll coating, plate coating, die coating, and gravure coating.
As a method for drying the coating film by evaporating the solvent in the coating film, conventionally known drying methods such as hot air drying, hot roll drying, and infrared irradiation are cited.
The conditions for drying the coating film are, for example, 80 to 150 ℃ and 30 seconds to 5 minutes, more preferably 90 to 120 ℃ and 1 minute to 4 minutes. By drying the coating film at 90 ℃ or higher, the coating film can be dried easily even in a drying time of 5 minutes or less, and the productivity is excellent.
The adhesive sheet for sealing equipment of the present invention satisfies the following formula (1).
[ math figure 2]
x-y≥20 (1)
Where x is a peeling force between the first peeling film and the adhesive layer (hereinafter, sometimes referred to as "first peeling force". Its unit is "mN/50 mm"), and y is a peeling force between the second peeling film and the adhesive layer (hereinafter, sometimes referred to as "second peeling force". Its unit is "mN/50 mm").
By setting the value of x-y to 20 or more, the release film can be peeled without breaking the adhesive layer. The value of x-y is preferably 25 to 500, more preferably 30 to 300.
The first peel force is usually 30 to 200mN/50mm, preferably 40 to 150mN/50mm. When the first peeling force is in such a range, the second peeling film is peeled off and the adhesive layer is adhered to the adherend, and then peeling of the adhesive layer from the adherend does not occur at the time of peeling off the first peeling film, so that the first peeling film can be easily removed.
The second peeling force is usually 5 to 50mN/50mm, preferably 10mN/50mm or more and less than 30mN/50mm.
The first peel force and the second peel force can be measured by the methods described in the examples, respectively.
The adhesive sheet for sealing a device, which satisfies the formula (1) and in which the respective peeling forces of the first peeling force and the second peeling force are in the above-described ranges, can be efficiently produced by appropriately selecting two release films based on the tendency shown below, for example.
In general, when the release film becomes thicker, the release force tends to be higher.
In the above method for producing the adhesive sheet for sealing a device, the peel force between the release film (a) to be coated with the coating liquid and the adhesive layer tends to be higher than the peel force between the release film (B) and the adhesive layer which are overlapped after the formation of the adhesive layer. Therefore, in this manufacturing method, in order to increase the difference between the first peeling force and the second peeling force, it is preferable to manufacture using the first peeling film as the peeling film (a).
In addition, when the release film (B) is heated while being overlapped with the adhesive layer, the release force between the release film and the adhesive layer tends to be higher than when the release film is operated at room temperature. Therefore, when the second release film is used as the release film (B), it is preferable to overlap the release film (B) and the adhesive layer at room temperature in order to increase the difference between the first release force and the second release force.
When a release film having a release layer made of a silicone resin is selected as the two release films, the following tends to be present. As a representative example of the silicone-based resin, there is an addition-reaction type silicone resin obtained from a first organopolysiloxane having at least 2 alkenyl groups (e.g., vinyl groups) in 1 molecule and a second organopolysiloxane having at least 2 hydrosilyl groups in 1 molecule (conforming to a crosslinking agent). At this time, the rigidity of the skeleton of the addition reaction type silicone resin affects the hardness of the release agent layer and the release force of the release film. In addition, when silicone resin is added to the addition reaction type silicone resin, the surface polarity can be adjusted according to the blending amount of silicone resin, and the peeling force can be adjusted.
The method for producing the device sealing body using the adhesive sheet for device sealing of the present invention is not particularly limited. For example, the following steps (a 1) to (a 5) and steps (b 1) to (b 5) are performed to seal an object to be sealed (equipment) to manufacture an equipment seal.
Step (a 1): and peeling off the second release film of the adhesive sheet for equipment seal.
Step (a 2): the adhesive layer exposed by performing the step (a 1) is adhered to the object (device) to be sealed.
Step (a 3): and (c) peeling and removing the first peeling film from the substance obtained in the step (a 2).
Step (a 4): the adhesive layer exposed by the step (a 3) is adhered to a substrate (glass plate, gas barrier film, etc.).
Step (a 5): the adhesive layer containing the substance obtained in the step (a 4) is cured by a specific means to form an adhesive cured product layer.
Step (b 1): and peeling off the second release film of the adhesive sheet for equipment seal.
Step (b 2): the adhesive layer exposed by the step (b 1) is adhered to a substrate (glass plate, gas barrier film, etc.).
Step (b 3): and (b) peeling and removing the first peeling film from the substance obtained in the step (b 2).
Step (b 4): the adhesive layer exposed by the step (b 3) is adhered to the object (device) to be sealed.
Step (b 5): the adhesive layer containing the substance obtained in the step (b 4) is cured by a specific means to form an adhesive cured product layer.
In the method for manufacturing the device sealing body, in the step (a 2) or the step (b 2), the adhesion of the adhesive layer to the object to be sealed or the substrate is preferably performed in a room temperature environment from the viewpoints of ease of operation and productivity. Likewise, the step (b 4) is preferably performed in a room temperature environment.
In the adhesive sheet for sealing a device of the present invention, the release film can be peeled off without breaking the adhesive layer.
Further, the adhesive cured product layer formed using the adhesive layer constituting the adhesive sheet for sealing a device of the present invention is excellent in adhesive strength and water vapor barrier property. Therefore, the adhesive sheet for device sealing of the present invention can be suitably used as a material for forming a sealing material in a device sealing body.
The device sealing body is not particularly limited. Examples of the device sealing body include organic EL devices such as an organic EL display and an organic EL lighting; a liquid crystal display; electronic paper; solar cells such as inorganic solar cells and organic thin film solar cells. When the adhesive cured product layer obtained from the adhesive layer constituting the adhesive sheet for device sealing of the present invention is transparent, the adhesive sheet for device sealing of the present invention can be suitably used as an organic EL device such as an organic EL display or an organic EL lighting; a liquid crystal display; and a sealing material for use in optical devices such as electronic paper.
Examples
Hereinafter, the present invention will be described in more detail by way of examples. However, the present invention is not limited to the following examples at all.
The parts and% in each example are mass references unless otherwise specified.
[ method for measuring storage elastic modulus ]
(1) Storage modulus of elasticity of adhesive layer
The adhesive layers of the device sealing adhesive sheets obtained in examples or comparative examples were laminated to a thickness of 1mm or more at 23℃using a laminator, and the resulting laminate was used as a test sample and its storage elastic modulus was measured.
That is, the storage elastic modulus was measured using a storage elastic modulus measuring apparatus (trade name: physica MCR301, manufactured by Anton Paar Co.) under conditions of a frequency of 1Hz, a strain of 1% and a temperature rise rate of 3 ℃/min, to obtain a storage elastic modulus value at 23 ℃.
(2) Storage elastic modulus of adhesive cured product layer
The adhesive layers of the device sealing adhesive sheets obtained in examples and comparative examples were laminated to a thickness of 200 μm or more at 23℃using a laminator, and the resultant laminate was heated at 100℃for 1 hour to obtain a cured product thereof. The cured product was used as a measurement sample, and the storage elastic modulus was measured.
Specifically, the storage elastic modulus in the temperature range of-20℃to +90℃was measured using a storage elastic modulus measuring apparatus (trade name: DMAQ800, manufactured by TA clamping Co.) under the conditions of a frequency of 11Hz, an amplitude of 5 μm, and a temperature rise rate of 3℃per minute, to obtain a value of the storage elastic modulus at +90℃.
[ measurement of the peel force of the first and second Release films ]
The adhesive sheets for sealing devices manufactured in practical examples and comparative examples were cut to obtain test pieces having a width of 50mm and a length of 150 mm. The test piece was subjected to 180 DEG peel test at a peeling rate of 300 mm/min under conditions of a temperature of 23℃and a relative humidity of 50%.
That is, the adhesive layer exposed by peeling the second release film of the sealing adhesive sheet for equipment was superimposed on alkali-free glass at a temperature of 23 ℃ and a relative humidity of 50%, and after pressure bonding with a pressure bonding roller, the peeling test was performed to obtain the peeling force of the first release film. In the fracture evaluation of the adhesive layer at the time of peeling the second release film described below, the peeling was performed with care by a manual operation so that a part of the adhesive layer was not transferred to the second release film at the time of peeling the second release film, with respect to the sample evaluated as "B".
On the other hand, in the peeling test of the second peeling film, the test piece was obtained in a state in which a double-sided tape was attached to the exposed surface of the first peeling film, and the test piece was attached to alkali-free glass with the double-sided tape, to obtain a laminate of a layer structure of "alkali-free glass/double-sided tape/first peeling film/adhesive layer/second peeling film". Thereafter, the laminate was subjected to a peel test of the second release film in the same manner as the first release film to obtain a peel force.
[ evaluation of fracture of adhesive layer when peeling off the second Release film ]
In the measurement of the peel force of the second release film, the state of the adhesive layer transferred to the second release film after the peeling test was observed, and the fracture evaluation of the adhesive layer was performed according to the following criteria.
A: the adhesive layer is not transferred to the second release film.
B: the adhesive layer breaks and a portion of the adhesive layer is transferred to the second release film.
[ evaluation of adhesion suitability of an adhesive layer to an object to be sealed ]
In the measurement of the peel force of the first release film, the state of the adhesive layer floating from the alkali-free glass was observed before the peeling test, and the evaluation a was made when there was no floating, and the evaluation B was made when there was floating.
[ Compounds and Release films used in examples or comparative examples ]
Cyclic ether compound (AL 1): hydrogenated bisphenol A type glycidyl ether epoxy resin (trade name: YX8034, liquid at 25 ℃ C., epoxy equivalent: 270 g/eq) manufactured by Mitsubishi chemical company
Cyclic ether compound (AL 2): hydrogenated bisphenol A type glycidyl ether epoxy resin (trade name: YX8000, manufactured by Mitsubishi chemical company, liquid at 25 ℃ C., epoxy equivalent: 205 g/eq)
Binder resin (B1): phenoxy resin (trade name: YX7200B35, glass transition temperature: 150 ℃ C. Manufactured by Mitsubishi chemical company.)
Curing catalyst (C1): imidazole curing catalyst (trade name: dipyr 3, manufactured by Sichuang chemical industry Co., ltd.; dipyr 2E4 MZ)
Curing catalyst (C2): thermal cationic polymerization initiator (trade name: siB 3, manufactured by Sanxinchu chemical Co., ltd.)
Silane coupling agent (D1): 8-epoxypropoxy octyl trimethoxysilane (trade name: KBM4803, manufactured by Xinyue chemical industry Co., ltd.)
Is a release film (E1): the trade name of the brand by the trade company "doctor solution": SP-PET752150
Is a release film (E2): the trade name of the brand by the trade company "doctor solution": SP-PET381130
And (c) a release film (E3): the trade name of the brand by the trade company "doctor solution": SP-PET751130
Release film (E4): the trade name of the brand by the trade company "doctor solution": SP-PET381031.
[ example 1 ]
100 parts by mass of a binder resin (B1), 250 parts by mass of a cyclic ether compound (AL 1), 2 parts by mass of a curing catalyst (C1), and 0.2 part by mass of a silane coupling agent (D1) were dissolved in methyl ethyl ketone to prepare a coating liquid.
The coating liquid was applied to the release treated surface of the release film (E1) (first release film), and the resulting coating film was dried at 100℃for 2 minutes to form an adhesive layer having a thickness of 15. Mu.m. The release treatment surface of the release film (E2) (second release film) was stuck to the adhesive layer to obtain an adhesive sheet for sealing a device.
[ example 2 ]
In example 1, an adhesive sheet for sealing a device was obtained in the same manner as in example 1, except that 130 parts by mass of the cyclic ether compound (AL 2) was used in place of the cyclic ether compound (AL 1) and 3.8 parts by mass of the curing catalyst (C2) was used in place of the curing catalyst (C1).
Comparative example 1
In example 1, an adhesive sheet for sealing a device was obtained in the same manner as in example 1, except that 250 parts by mass of the cyclic ether compound (AL 2) was used in place of the cyclic ether compound (AL 1) and 2 parts by mass of the curing catalyst (C2) was used in place of the curing catalyst (C1).
Comparative example 2
In example 1, an adhesive sheet for sealing a device was obtained in the same manner as in example 1, except that the release film (E3) (first release film) was used instead of the release film (E1), and the release film (E4) (second release film) was used instead of the release film (E2).
[ comparative example 3 ]
In example 1, an adhesive sheet for sealing a device was obtained in the same manner as in example 1, except that 100 parts by mass of the cyclic ether compound (AL 2) was used instead of the cyclic ether compound (AL 1), and 5 parts by mass of the curing catalyst (C2) was used instead of the curing catalyst (C1).
The composition of the adhesive layer and the test results of the adhesive sheets for sealing devices of examples 1 to 2 and comparative examples 1 to 3 are shown below.
TABLE 1
In the adhesive sheets for sealing devices of examples 1 and 2, the second release film can be peeled without breaking the adhesive layer. The adhesive layer of the adhesive sheet for sealing equipment has sufficient adhesive strength at room temperature and excellent adhesion suitability.
On the other hand, in the adhesive sheet for sealing a device of comparative example 1, since the storage elastic modulus of the adhesive layer at 23 ℃ is too low, the adhesive layer breaks when the second release film is peeled off.
In the adhesive sheet for sealing a device of comparative example 2, the difference in the peeling forces between the two release films is small, and therefore, the adhesive layer breaks when the second release film is peeled.
In the adhesive sheet for sealing a device of comparative example 3, since the adhesive layer has a large storage elastic modulus at 23 ℃, the adhesive layer is not broken when the second release film is peeled off even if the difference between the peeling forces of the two release films is small. However, the adhesive layer does not have sufficient adhesive force at room temperature, and has poor adhesion suitability.

Claims (8)

1. An adhesive sheet for sealing a device, comprising a first release film, a second release film, and an adhesive layer sandwiched between the first release film and the second release film, wherein all of the following requirements (I) to (IV) are satisfied,
Essential condition (I): the adhesive layer is a layer containing 1 or more compounds having cyclic ether groups;
essential condition (II): the adhesive layer has a storage elastic modulus at 23 ℃ of 5.0X10 5 Pa or more and 3.0X10 7 Pa or less;
essential condition (III): the device sealing adhesive sheet satisfies the following formula (1) with a value of a peeling force between the first peeling film and the adhesive layer being denoted as x (mN/50 mm) and a value of a peeling force between the second peeling film and the adhesive layer being denoted as y (mN/50 mm):
[ mathematics 1]
x-y≥20 (1)；
Essential condition (IV): at least 1 of the compounds having a cyclic ether group is a compound that is liquid at 25 ℃, and the content of the compound having a cyclic ether group that is liquid at 25 ℃ is 53 mass% or more with respect to the entire adhesive layer.
2. The adhesive sheet for device sealing according to claim 1, wherein the adhesive layer is a layer further containing a thermal cationic polymerization initiator.
3. The adhesive sheet for sealing equipment according to claim 2, wherein at least 1 of the compounds having a cyclic ether group is a compound having a glycidyl ether group.
4. The adhesive sheet for sealing a device according to claim 1, wherein the adhesive layer is a layer further containing an adhesive resin.
5. The adhesive sheet for sealing equipment according to claim 4, wherein the binder resin is a resin having a glass transition temperature of 90 ℃ or higher.
6. The adhesive sheet for sealing equipment according to claim 1, wherein the layer obtained by curing the adhesive layer has a storage elastic modulus at 90℃of 1X 10 8 Pa or more.
7. The adhesive sheet for sealing equipment according to claim 1, wherein a value x of a peeling force between the first peeling film and the adhesive layer is 30 to 200mN/50mm.
8. A method of manufacturing an equipment enclosure, comprising: a step of peeling the second peeling film from the device sealing adhesive sheet according to claim 1; and adhering the exposed adhesive layer to the object to be sealed or the substrate at a temperature of 20-30 ℃.
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JP7368202B2 (en) * 2019-11-29 2023-10-24 リンテック株式会社 Sealing sheet
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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104781360A (en) * 2012-12-17 2015-07-15 三菱树脂株式会社 Base-less double-sided adhesive sheet
CN107820512A (en) * 2015-06-09 2018-03-20 株式会社Lg化学 Bonding film and the organic electronic device for including it
JPWO2018047919A1 (en) * 2016-09-07 2018-09-06 リンテック株式会社 Adhesive composition, sealing sheet, and sealing body

Family Cites Families (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS561202B2 (en) 1972-10-12 1981-01-12
JP3632601B2 (en) * 2001-02-02 2005-03-23 荒川化学工業株式会社 COATING COMPOSITION, COATING AGENT CURED FILM AND PROCESS FOR PRODUCING THE SAME
JP3654351B2 (en) 2001-07-27 2005-06-02 荒川化学工業株式会社 Silane-modified epoxy resin, production method thereof, resin composition, semi-cured product and cured product
JP4225162B2 (en) 2003-08-18 2009-02-18 日立化成工業株式会社 Sealing film
JP5651421B2 (en) * 2010-10-07 2015-01-14 三井化学株式会社 Sealing composition and sealing sheet using the same
JP5364075B2 (en) * 2010-11-12 2013-12-11 日東電工株式会社 Method for producing thermosetting resin composition cured product and cured product obtained thereby
JP5364078B2 (en) * 2010-11-18 2013-12-11 日東電工株式会社 Method for producing thermosetting resin composition cured product and cured product obtained thereby
US9263360B2 (en) * 2012-07-06 2016-02-16 Henkel IP & Holding GmbH Liquid compression molding encapsulants
JP6091202B2 (en) * 2012-12-17 2017-03-08 三菱樹脂株式会社 Substrate-less double-sided adhesive sheet
JP6249345B2 (en) * 2013-03-22 2017-12-20 三菱瓦斯化学株式会社 Resin composition, prepreg, laminate and printed wiring board
CN105026493B (en) 2013-06-10 2017-07-07 三井化学株式会社 Thermoset composition, organic EL element face sealant and its solidfied material
JP6829960B2 (en) * 2015-11-27 2021-02-17 日東電工株式会社 Adhesive sheet and adhesive sheet with release film
TWI747950B (en) * 2016-09-07 2021-12-01 日商琳得科股份有限公司 Adhesive composition, sealing sheet and sealing body
WO2018047422A1 (en) * 2016-09-07 2018-03-15 リンテック株式会社 Gas barrier laminate and sealed body
JP2018095679A (en) 2016-12-08 2018-06-21 三井化学株式会社 Sheet-like seal material, display element seal material, surface sealing material for organic el element, organic el device, and method for manufacturing organic el device
EP3613780A4 (en) * 2017-04-19 2021-03-24 Showa Denko K.K. Curable resin composition, cured product thereof, and structure including cured product thereof

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104781360A (en) * 2012-12-17 2015-07-15 三菱树脂株式会社 Base-less double-sided adhesive sheet
CN107820512A (en) * 2015-06-09 2018-03-20 株式会社Lg化学 Bonding film and the organic electronic device for including it
JPWO2018047919A1 (en) * 2016-09-07 2018-09-06 リンテック株式会社 Adhesive composition, sealing sheet, and sealing body

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