CN112368353A - Adhesive sheet for sealing device and method for manufacturing device sealing body - Google Patents

Adhesive sheet for sealing device and method for manufacturing device sealing body Download PDF

Info

Publication number
CN112368353A
CN112368353A CN201980040146.XA CN201980040146A CN112368353A CN 112368353 A CN112368353 A CN 112368353A CN 201980040146 A CN201980040146 A CN 201980040146A CN 112368353 A CN112368353 A CN 112368353A
Authority
CN
China
Prior art keywords
adhesive layer
release film
adhesive
adhesive sheet
sealing
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CN201980040146.XA
Other languages
Chinese (zh)
Other versions
CN112368353B (en
Inventor
西嶋健太
长谷川树
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Lintec Corp
Original Assignee
Lintec Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Lintec Corp filed Critical Lintec Corp
Publication of CN112368353A publication Critical patent/CN112368353A/en
Application granted granted Critical
Publication of CN112368353B publication Critical patent/CN112368353B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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

Landscapes

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

Abstract

The present invention relates to an adhesive sheet for device sealing 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 requirements relating to components contained in the adhesive layer, requirements relating to the storage elastic modulus of the adhesive layer, and requirements relating to the peel strength of the release film, and a method for manufacturing a device sealed body using the adhesive sheet for device sealing. 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 device and method for manufacturing device sealing body
Technical Field
The present invention relates to an apparatus sealing adhesive sheet having two release films and an adhesive layer sandwiched between the release films, and a method for producing an apparatus sealing body using the apparatus sealing adhesive sheet.
Background
In recent years, organic EL elements have attracted attention as light-emitting elements capable of emitting light with high luminance 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, and light emission uniformity tend to decrease with time.
As a cause of the problem of the decrease in the light emission characteristics, it is considered that oxygen, moisture, or the like enters the inside of the organic EL element to degrade the electrode and the organic layer. Therefore, 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 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 has good sealing performance.
Documents of the prior art
Patent document
Patent document 1: japanese patent laid-open publication No. 2018-95679.
Disclosure of Invention
Problems to be solved by the invention
However, as shown in patent document 1: when the sealing material is formed using an adhesive layer, a new problem may occur.
That is, the adhesive layer is usually manufactured and stored in a state of being sandwiched between two release films, and the release films are peeled and removed at the time of use, but the first release film may not be peeled cleanly, and the adhesive layer may be broken.
The present invention has been made to solve the above problems, and an object of the present invention is to provide an adhesive sheet for device sealing which has two release films and an adhesive layer sandwiched between the release films and can release the release films without breaking the adhesive layer, and a method for producing a device sealing body using the adhesive sheet for device sealing.
Means for solving the problems
In order to solve the above problems, the present inventors have conducted extensive studies on an adhesive sheet for device sealing, which comprises two release films and an adhesive layer containing a compound having a cyclic ether group and sandwiched between the release films.
As a result, they found that: the present inventors have completed the present invention by obtaining an adhesive sheet for device sealing which can peel a release film without breaking an adhesive layer by satisfying both the requirement relating to the storage elastic modulus of the adhesive layer at 23 ℃ and the requirement relating to the peeling force of two release films.
Thus, the present invention provides the adhesive sheet for device sealing [ 1] to [ 9 ] and the method for producing a device sealing body [ 10 ] described below.
[ 1] an adhesive sheet for sealing equipment, which comprises 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 following requirements (I) to (III).
Requirement (I): the adhesive layer is a layer containing 1 or2 or more kinds of compounds having a cyclic ether group.
Requirement (II): the storage elastic modulus of the adhesive layer at 23 ℃ is 5.0X 105Pa or more and 3.0X 107Pa or less.
Requirement (III): when the value of the peel force between the first release film and the adhesive layer is represented by x (mN/50mm) and the value of the peel force between the second release film and the adhesive layer is represented by y (mN/50mm), the adhesive sheet for sealing a device satisfies the following formula (1).
[ mathematical formula 1]
x-y≥20 (1)。
The adhesive sheet for sealing an apparatus according to [ 1], wherein at least 1 of the compounds having a cyclic ether group is a compound which is liquid at 25 ℃.
[ 3 ] the adhesive sheet for sealing equipment according to [ 2], wherein the content of the compound having a cyclic ether group that is liquid at 25 ℃ is 53% by mass or more based on the entire adhesive layer.
[ 4 ] the adhesive sheet for sealing equipment 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 device sealing according to [ 4 ], wherein at least 1 of the compounds having a cyclic ether group is a compound having a glycidyl ether group.
[ 6 ] the adhesive sheet for sealing equipment according to any one of [ 1] to [ 5 ], wherein the adhesive layer is a layer further containing a binder resin.
[ 7 ] the adhesive sheet for sealing equipment according to [ 6 ], wherein the binder resin is a resin having a glass transition temperature of 90 ℃ or higher.
[ 8 ] the adhesive sheet for sealing equipment according to any one of [ 1] to [ 7 ], wherein a layer obtained by curing the adhesive layer has a storage elastic modulus of 1X 10 at 90 ℃8Pa or above.
[ 9 ] 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 release film and the adhesive layer is 30 to 200mN/50 mm.
A method of manufacturing an equipment enclosure, comprising: a step of peeling the second release film from the adhesive sheet for device sealing described in any one of [ 1] to [ 9 ]; and a step of adhering the exposed adhesive layer to the object to be sealed or the substrate in a temperature environment of 20 to 30 ℃.
Effects of the invention
According to the present invention, there is provided an adhesive sheet for sealing equipment, which comprises two release films and an adhesive layer sandwiched between the release films and can release the release films without breaking the adhesive layer; and a method for producing a device sealing body using the device sealing adhesive sheet.
Detailed Description
The device sealing adhesive sheet of the present invention is a device sealing adhesive sheet having a first release film and a second release film, and an adhesive layer sandwiched between the first release film and the second release film, and satisfies all of requirement (I), requirement (II), and requirement (III) described above.
In the present invention, the "first release film" refers to a release film having a high peeling force among two release films, and the "second release film" refers to a release film having a low peeling force among the two release films.
The "adhesive layer" is a layer obtained by forming a curable adhesive into a film, and has 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 layer". The adhesive cured layer is used as a sealing material.
In the present invention, "cured" means that the cyclic ether group contained in the adhesive layer reacts to increase the cohesive force and the storage elastic modulus of the layer.
[ adhesive layer ]
(Compound having Cyclic Ether group)
The adhesive layer contains 1 or2 or more kinds of compounds having a cyclic ether group (hereinafter, sometimes referred to as "cyclic ether compound (a)").
By curing the adhesive layer containing the cyclic ether compound (a), a sealing material having high adhesive strength and excellent water vapor barrier properties 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 800 g/eq.
By curing the adhesive layer containing the cyclic ether compound (a) having a cyclic ether equivalent in the above range, a sealing material having higher adhesive strength and more excellent water-barrier properties 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 oxetane group (oxetanyl group), a tetrahydrofuranyl group, and a tetrahydropyranyl group. Among these, from the viewpoint of forming a sealing material having higher adhesive strength, the cyclic ether group is preferably an ethylene oxide group or an oxetane group, and more preferably an ethylene oxide group.
For the same reason, the cyclic ether compound (a) preferably has 2 or more ethylene oxide groups or oxetane groups in the molecule, and more preferably has 2 or more ethylene oxide groups in the molecule.
Examples of the compound having an oxirane group in a molecule include an aliphatic epoxy compound (excluding an alicyclic epoxy compound), an aromatic epoxy compound, and an alicyclic epoxy compound.
Examples of the aliphatic epoxy compound include monofunctional epoxy compounds such as glycidyl etherate of aliphatic alcohol and glycidyl ester of alkyl carboxylic acid;
and polyfunctional epoxy compounds such as polyglycidyl ether compounds of aliphatic polyhydric alcohols or alkylene oxide adducts thereof, and polyglycidyl esters of aliphatic long-chain polybasic acids.
Representative examples of the aliphatic epoxy compound 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 ethers; 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 dicyclopentadiene dimethanol diglycidyl ether; polyglycidyl etherates of polyether polyols obtained by adding 1 or2 or more types of alkylene oxides to aliphatic polyhydric alcohols such as propylene glycol, trimethylolpropane, and glycerin; diglycidyl esters of aliphatic long-chain dibasic acids; monoglycidyl ether of aliphatic higher alcohol, glycidyl ester of higher fatty acid, epoxidized soybean oil, epoxidized octyl stearate, epoxidized butyl stearate, epoxidized polybutadiene, and the like.
Further, as the aliphatic epoxy compound, commercially available products can be used. Commercially available products include デナコール EX-121, デナコール EX-171, デナコール EX-192, デナコール EX-211, デナコール EX-212, デナコール EX-313, デナコール EX-314, デナコール EX-321, デナコール EX-411, デナコール EX-421, デナコール EX-512, デナコール EX-521, デナコール EX-611, デナコール EX-612, デナコール EX-614, デナコール EX-622, デナコール EX-810, デナコール EX-811, デナコール EX-850, デナコール EX-851, デナコール EX-821, デナコール EX-830, デナコール EX-832, etc, デナコール EX-841, デナコール EX-861, デナコール EX-911, デナコール EX-941, デナコール EX-920, デナコール EX-931(ナガセケムテックス corporation);
エポライト M-1230, エポライト 40E, エポライト 100E, エポライト 200E, エポライト 400E, エポライト 70P, エポライト 200P, エポライト 400P, エポライト 1500NP, エポライト 1600, エポライト 80MF, エポライト 100MF (manufactured by Kyoeisha chemical Co., Ltd.);
アデカグリシロール ED-503, アデカグリシロール ED-503G, アデカグリシロール ED-506, and アデカグリシロール ED-523T (manufactured by ADEKA).
Examples of the aromatic epoxy compound include mono/polyglycidyl etherates of phenols having at least 1 aromatic ring such as phenol, cresol, and butylphenol, or alkylene oxide adducts thereof; epoxy compounds having an aromatic heterocyclic ring, and the like.
Representative examples of the aromatic epoxy compound include glycidyl etherate compounds of bisphenol a and bisphenol F, and compounds obtained by further adding alkylene oxide to bisphenol a and bisphenol F, and epoxy novolac resins;
mono/polyglycidyl etherates of aromatic compounds having 2 or more phenolic hydroxyl groups such as resorcinol, hydroquinone, and catechol;
glycidyl etherates of aromatic compounds having 2 or more alcoholic hydroxyl groups such as phenyl dimethanol, phenyl diethanol, and phenyl dibutanol;
glycidyl esters of polybasic acid aromatic compounds having 2 or more carboxylic acids such as phthalic acid, terephthalic acid, trimellitic acid, etc., glycidyl esters of benzoic acid, epoxides of styrene oxide or divinylbenzene;
and epoxy compounds having a triazine skeleton such as 2,4, 6-tris (glycidyl ether oxy) -1,3, 5-triazine.
Further, as the aromatic epoxy compound, a commercially available product can be used. Commercially available products include デナコール EX-146, デナコール EX-147, デナコール EX-201, デナコール EX-203, デナコール EX-711, デナコール EX-721, オンコート EX-1020, オンコート EX-1030, オンコート EX-1040, オンコート EX-1050, オンコート EX-1051, オンコート EX-1010, オンコート EX-1011 and オンコート 1012 (manufactured by ナガセケムテックス Co., Ltd.);
オグソール PG-100, オグソール EG-200, オグソール EG-210, オグソール EG-250 (manufactured by Osaka ガスケミカル Co., Ltd.);
HP4032, HP4032D, HP4700 (DIC, supra);
ESN-475V (manufactured by Nippon iron ケミカル & マテリアル Co., Ltd.);
JER (original エピコート) YX8800 (made by Mitsubishi ケミカル, Inc. above);
マープルーフ G-0105SA and マープルーフ G-0130SP (manufactured by Nichisu oil Co., Ltd.);
エピクロン N-665, エピクロン HP-7200 (produced by DIC Co., Ltd.);
EOCN-1020, EOCN-102S, EOCN-103S, EOCN-104S, XD-1000, NC-3000, EPPN-501H, EPPN-501HY, EPPN-502H, NC-7000L (manufactured by Nippon chemical Co., Ltd.);
アデカレジン EP-4000, アデカレジン EP-4005, アデカレジン EP-4100 and アデカレジン EP-4901 (manufactured by ADEKA Co., Ltd.);
TECHMORE VG-3101L (manufactured by プリンテック Co., Ltd.);
TEPIC-FL, TEPIC-PAS, TEPIC-UC (manufactured by Nissan chemical Co., Ltd.).
Examples of the alicyclic epoxy compound include: a polyglycidyl etherate of a polyhydric alcohol having at least 1 or more alicyclic structures; or a cyclohexene oxide or cyclopentane oxide-containing compound obtained by epoxidizing a cyclohexene ring or cyclopentene ring-containing compound with an oxidizing agent.
Representative examples of the alicyclic epoxy compounds include hydrogenated bisphenol A diglycidyl ether, 3, 4-epoxycyclohexylmethyl-3, 4-epoxycyclohexanecarboxylate, 3, 4-epoxy-1-methylcyclohexyl-3, 4-epoxy-1-methylhexanecarboxylate, 6-methyl-3, 4-epoxycyclohexylmethyl-6-methyl-3, 4-epoxycyclohexanecarboxylate, 3, 4-epoxy-3-methylcyclohexylmethyl-3, 4-epoxy-3-methylcyclohexanecarboxylate, 3, 4-epoxy-5-methylcyclohexylmethyl-3, 4-epoxy-5-methylcyclohexanecarboxylate, hydrogenated bisphenol A diglycidyl ether, 3, 4-epoxycyclohexylmethyl-3, 4-epoxycyclohexanecarboxylate, 3, 4-epoxycyclohexylmethyl-3, 4-epoxymethylcyclohexanecarboxylate, and the like, Bis (3, 4-epoxycyclohexylmethyl) adipate, 3, 4-epoxy-6-methylcyclohexanecarboxylate, methylenebis (3, 4-epoxycyclohexane), propane-2, 2-diyl-bis (3, 4-epoxycyclohexane), 2-bis (3, 4-epoxycyclohexyl) propane, dicyclopentadiene diepoxide, ethylenebis (3, 4-epoxycyclohexane carboxylate), dioctylphthalate oxide, di (2-ethylhexyl) epoxyhexahydrophthalate, 1-epoxyethyl-3, 4-epoxycyclohexane, 1, 2-epoxy-2-epoxyethylcyclohexane, α -pinene oxide, limonene dioxide and the like.
Further, as the alicyclic epoxy compound, a commercially available one can also be used. Examples of commercially available products include セロキサイド 2021P, セロキサイド 2081, セロキサイド 2000, and セロキサイド 3000(ダイセル, manufactured by co.); エポライト 4000 (manufactured by Kyoeisha chemical Co., Ltd.); YX8000 and YX8034 (manufactured by Mitsubishi ケミカル Co., Ltd.); アデカレジン EP-4088S, アデカレジン EP-4088L, アデカレジン EP-4080E (manufactured by ADEKA Co., Ltd.).
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 cited. Examples of such a compound include エピクロン HP-7200 (manufactured by DIC).
Among these, from the viewpoint of reducing the dielectric constant of the adhesive cured layer, the compound having an oxirane group is preferably an alicyclic epoxy resin.
When a thermal cationic polymerization initiator is used as a curing catalyst to be described later, the compound having an oxirane group is preferably a compound having a glycidyl ether group. Glycidyl ether groups tend to undergo cationic polymerization relatively gently. Therefore, in the case where a step of heating a composition containing components constituting the adhesive layer (for example, a step of heating to 90 ℃ or higher) is present in the step of producing the adhesive layer, the polymerization reaction of the glycidyl ether group is difficult to proceed, 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 preferably 90% by mass or more, relative to the whole of the compound having a cyclic ether group.
Examples of the compound having an oxetanyl group in the molecule include 3, 7-bis (3-oxetanyl) -5-oxanonane, 1, 4-bis [ (3-ethyl-3-oxetanylmethoxy) methyl ] benzene, 1, 2-bis [ (3-ethyl-3-oxetanylmethoxy) methyl ] ethane, 1, 3-bis [ (3-ethyl-3-oxetanylmethoxy) methyl ] propane, ethylene glycol bis (3-ethyl-3-oxetanylmethyl) ether, triethylene glycol bis (3-ethyl-3-oxetanylmethyl) ether, tetraethylene glycol bis (3-ethyl-3-oxetanylmethyl) ether, 1, 4-bis (3-ethyl-3-oxetanylmethoxy) butane, and mixtures thereof, Difunctional aliphatic oxetane compounds such as 1, 6-bis (3-ethyl-3-oxetanylmethoxy) 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, commercially available products can be used. Examples of commercially available products include 2-hydroxyethyl vinyl ether, diethylene glycol monovinyl ether, and 4-hydroxybutyl vinyl ether (manufactured by PELLE PETROL. Co., Ltd.);
アロンオキセタン OXT-121, OXT-221, EXOH, POX, OXA, OXT-101, OXT-211, OXT-212 (manufactured by east Asia synthetic Co., Ltd.);
エタナコール OXBP and OXTP (made by Utsu corporation).
These cyclic ether compounds (a) may be used alone in 1 kind or in combination of 2 or more kinds.
The content of the cyclic ether compound (a) in the adhesive layer (when 2 or more cyclic ether compounds (a) are contained, the total amount thereof) is preferably 45 to 90 mass%, more preferably 50 to 85 mass%, and still more preferably 60 to 80 mass% with respect to the entire adhesive layer.
By setting the content of the cyclic ether compound (a) within the above range, an adhesive cured layer having a high storage elastic modulus at 90 ℃ can be easily obtained.
At least 1 of the cyclic ether compounds (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 is one of the aggregated states of substances, and has a substantially constant volume but does not have a constant shape.
By using the cyclic ether compound (AL) which is liquid at 25 ℃, the storage elastic modulus of the adhesive layer at 23 ℃ can be suppressed from becoming excessively high. Therefore, an adhesive layer having sufficient adhesive strength at room temperature (the same applies below 20 to 30 ℃) can be easily obtained.
The cyclic ether equivalent weight of the cyclic ether compound (AL) that is liquid at 25 ℃ is preferably 150 to 1000g/eq, and 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) that is liquid at 25 ℃ (when 2 or more compounds are included, the total amount thereof) in the adhesive layer is preferably 53 mass% or more, more preferably 53 to 80 mass%, and still more preferably 54 to 65 mass% with respect to the entire adhesive layer. By setting the content of the cyclic ether compound (AL) that is liquid at 25 ℃ to 53 mass% or more with respect to the entire adhesive layer, an adhesive layer having sufficient adhesive force at around room temperature can be easily obtained. Further, an adhesive cured layer having a high storage elastic modulus at 90 ℃ can be easily obtained. Further, by setting the content of the cyclic ether compound (AL) that is liquid at 25 ℃ to 80 mass% or less with respect 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 a binder resin (B). The adhesive layer containing a binder 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 even more preferably 10,000 to 100,000, from the viewpoint of further 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 as a standard polystyrene equivalent by Gel Permeation Chromatography (GPC) using Tetrahydrofuran (THF) as a solvent.
When the adhesive layer contains the binder resin (B), the content of the binder resin (when 2 or more binder resins are contained, the total amount thereof) is preferably 5 to 50% by mass, and more preferably 10 to 45% by mass, based on the entire adhesive layer.
When the content of the binder resin (B) is within the above range, an adhesive layer having excellent shape retention and sufficient adhesive force can be easily obtained.
As described later, the storage elastic modulus of the adhesive cured layer at 90 ℃ was set to 1X 108Pa or more is preferable because the storage elastic modulus of the cured adhesive layer at 90 ℃ is likely to increase when the binder resin (B) is a resin having a glass transition temperature of 90 ℃ or more. Examples of the resin having a glass transition temperature of 90 ℃ or higher include phenoxy resins, polyimide resins, polyamideimide resins, polyvinyl butyral resins, polycarbonate resins, 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 alone in 1 kind or in combination of 2 or more kinds.
The binder resin (B) is preferably at least one selected from the group consisting of phenoxy resins and modified olefin resins, and is preferably a phenoxy resin from the viewpoint of increasing the storage elastic modulus of the adhesive cured layer at 90 ℃.
The phenoxy resin generally corresponds to an epoxy resin having a high molecular weight, and means a resin having a polymerization degree of about 100 or more.
The phenoxy resin used in the present invention preferably has a weight average molecular weight (Mw) of 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 value by Gel Permeation Chromatography (GPC) using Tetrahydrofuran (THF) as a solvent.
Phenoxy resins containing such high-molecular-weight epoxy resins are 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 epoxy equivalent value can be measured according to JIS K7236.
Examples of the phenoxy resin used in the present invention include bisphenol a type, bisphenol F type, bisphenol S type phenoxy resin, copolymer type phenoxy resin of bisphenol a type and bisphenol F type, 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 alone in 1 kind or in combination of 2 or more kinds.
The phenoxy resin can be obtained by a method in which a bifunctional phenol is reacted with an epihalohydrin to have a high molecular weight or by addition polymerization of a bifunctional epoxy resin with a bifunctional phenol.
For example, the compound can be obtained by reacting a bifunctional phenol with an epihalohydrin in the presence of an alkali metal hydroxide and in an inactive solvent at a temperature of 40 to 120 ℃. The epoxy resin composition can also be obtained by heating a bifunctional epoxy resin and a bifunctional phenol to 50 to 200 ℃ in the presence of a catalyst such as an alkali metal compound, an organophosphorus 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, under a condition that the concentration of the reaction solid content is 50 wt% or less, and causing an addition polymerization reaction.
The bifunctional phenol is not particularly limited as long as it is a compound 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 and bisphenol S; dihydroxybiphenyls such as 4, 4' -dihydroxybiphenyl; dihydroxyphenyl ethers such as bis (4-hydroxyphenyl) ether; and those obtained by introducing a linear alkyl group, a branched alkyl group, an aryl group, a methylol group, an allyl group, a cyclic aliphatic group, a halogen (e.g., tetrabromobisphenol a), a nitro group, or the like into the aromatic ring of the phenol skeleton; and polycyclic bifunctional 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 the carbon atom at the center of the bisphenol skeleton.
Examples of the epihalohydrin include epichlorohydrin, epibromohydrin, and epiiodohydrin.
In the present invention, a commercially available phenoxy resin may be used. Examples thereof include trade names manufactured by mitsubishi ケミカル: 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 Dongdu chemical Co., Ltd.: FX280, FX293, and FX293S (fluorene skeleton-containing phenoxy resin), trade name of mitsubishi ケミカル: jER1256, jER4250 (glass transition temperature: less than 85 ℃), jER4275 (glass transition temperature: 75 ℃), Nippon iron ケミカル & マテリアル, trade name: YP-50 (glass transition temperature: 84 ℃), YP-50S (both phenoxy resins containing bisphenol A skeleton), YP-70 (bisphenol A skeleton/bisphenol F skeleton copolymer phenoxy resin, glass transition temperature: less than 85 ℃), ZX-1356-2 (glass transition temperature: 72 ℃), etc. The glass transition temperature is shown for a substance whose glass transition temperature is already 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 olefin-based resin refers to a polymer containing a repeating unit derived from an olefin-based monomer. The olefin-based resin may be a polymer containing only a repeating unit derived from an olefin-based monomer, or may be a polymer containing a repeating unit derived from an olefin-based monomer and a repeating unit derived from a monomer copolymerizable with the olefin-based monomer.
The olefin-based monomer is preferably an alpha-olefin having 2 to 8 carbon atoms, more preferably ethylene, propylene, 1-butene, isobutylene or 1-hexene, and even more preferably ethylene or propylene. These olefinic monomers may be used alone in 1 kind or in combination of 2 or more kinds.
Examples of the monomer copolymerizable with the olefin-based 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 in 1 kind or in combination of 2 or more kinds.
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) acrylate copolymer.
The modifier used in the modification treatment of the olefin-based 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 carbamate 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 introducing (graft-modifying) a carboxyl group or a carboxylic anhydride group by reacting an unsaturated carboxylic acid or an unsaturated carboxylic anhydride (hereinafter, sometimes referred to as "unsaturated carboxylic acid or the like") with an olefin resin.
Examples of the unsaturated carboxylic acid which reacts with the olefin-based resin include unsaturated carboxylic acids such as maleic acid, fumaric acid, itaconic acid, citraconic acid, glutaconic acid, tetrahydrophthalic acid, and aconitic acid; unsaturated carboxylic acid anhydrides such as maleic anhydride, itaconic anhydride, glutaconic anhydride, citraconic anhydride, aconitic anhydride, norbornene dicarboxylic anhydride and tetrahydrophthalic anhydride.
These can be used alone in 1 or a combination of 2 or more. Among these, maleic anhydride is preferable because a sealing material having higher adhesive strength can be easily obtained.
The amount of the unsaturated carboxylic acid or the like to be reacted with the olefinic 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, per 100 parts by mass of the olefinic resin. By curing the adhesive layer containing the acid-modified olefin resin obtained in this manner, a sealing material having higher adhesive strength can be formed.
The method for introducing the unsaturated carboxylic acid unit or the unsaturated carboxylic acid anhydride unit into the olefin-based resin is not particularly limited. Examples of the method include the following methods: a method of reacting an olefin resin with an unsaturated carboxylic acid or the like by heating and melting the olefin resin 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 azonitrile; or a method of graft-copolymerizing an unsaturated carboxylic acid or the like with an olefin resin, such as a method of dissolving an olefin resin and an unsaturated carboxylic acid or the like in an organic solvent and then reacting them by heating and stirring in the presence of a radical generator.
Commercially available products can be used as the acid-modified olefin-based resin. Examples of commercially available products include アドマー (registered trademark) (manufactured by Mitsui chemical Co., Ltd.), ユニストール (registered trademark) (manufactured by Mitsui chemical Co., Ltd.), BondyRam (manufactured by Polyram Co., Ltd.), orevac (registered trademark) (manufactured by ARKEMA Co., Ltd.), モディック (registered trademark) (manufactured by Mitsubishi chemical Co., Ltd.).
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 resin can be determined as a standard polystyrene equivalent 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).
Examples of the curing catalyst include an anionic polymerization initiator and a cationic polymerization initiator.
From the viewpoint of performing a curing reaction in a short time and improving the storage stability of the adhesive layer, a cationic polymerization initiator is preferable.
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.
The cationic polymerization initiator includes a thermal cationic polymerization initiator and a photo cationic polymerization initiator, and is preferably a thermal cationic polymerization initiator 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 thermosetting device.
Thermal cationic polymerization initiators are compounds that are capable of generating cationic species to initiate polymerization upon 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 viewpoint of easy availability, easy availability of sealing materials having more excellent adhesion and transparency, and the like.
Examples of the sulfonium salt include triphenylsulfonium tetrafluoroborate, triphenylsulfonium hexafluoroantimonate, triphenylsulfonium hexafluoroarsenate, tris (4-methoxyphenyl) sulfonium hexafluoroarsenate, and diphenyl (4-phenylthiophenyl) sulfonium hexafluoroarsenate.
Further, as the sulfonium salt, a commercially available product can be used. As commercially available products, アデカオプトン SP-150, アデカオプトン SP-170, アデカオプトン CP-66, アデカオプトン CP-77 (manufactured by ADEKA Co., Ltd.), サンエイド SI-60L, サンエイド SI-80L, サンエイド SI-100L (manufactured by Sanxin chemical Co., Ltd.), CYRACURE UVI-6974, CYRACURE UVI-6990 (manufactured by ユニオン seed カーバイド Co., Ltd.), UVI-508, UVI-509 (manufactured by ゼネラル seed エレクトリック Co., Ltd.), FC-508, FC-509 (manufactured by ミネソタ seed 8282 アンド seed マニュファクチュアリング Co., Ltd.), CD-1010, CD-1011 (manufactured by サーストマー Co., Ltd.) and so forth are listed, CI series products (manufactured by Nippon Caoda Co., Ltd.), and the like.
Specific examples of the quaternary ammonium salts include tetrabutylammonium tetrafluoroborate, tetrabutylammonium hexafluorophosphate, tetrabutylammonium hydrogensulfate, tetraethylammonium tetrafluoroborate, tetraethylammonium p-toluenesulfonate, N-dimethyl-N-benzylaniline hexafluoroantimonate, N-dimethyl-N-benzylaniline tetrafluoroborate, N-dimethyl-N-benzylpyridinium hexafluoroantimonate, N-diethyl-N-benzyltrifluoromethanesulfonate, 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 the diazonium salt include americh (manufactured by アメリカン & seedpod キャン), ULTRASET (manufactured by ADEKA corporation), and the like.
Examples of the iodonium salts include diphenyliodonium hexafluoroarsenate, bis (4-chlorophenyl) iodonium hexafluoroarsenate, bis (4-bromophenyl) iodonium hexafluoroarsenate, and phenyl (4-methoxyphenyl) iodonium hexafluoroarsenate. Further, as commercially available products, UV-9310C (manufactured by toshiba シリコーン), Photoinitiator2074 (manufactured by ローヌ, seedling プーラン), UVE series products (manufactured by ゼネラル, seedling エレクトリック), FC series products (manufactured by ミネソタ, seedling マイニング, seedling アンド, seedling マニュファクチュアリング) and the like may be used.
The photo cation polymerization initiator is a compound capable of generating a cation species to initiate polymerization by light irradiation.
Examples of the photo cation polymerization initiator include aromatic sulfonium salts, aromatic iodonium salts, aromatic diazonium salts, and thioxanthone onium salts.
The aromatic sulfonium salt is a salt having an aromatic sulfonium as a cation moiety. Further, as the anion moiety, BF is possessed4 -、PF6 -、SbF6 -And (4) plasma.
Examples of the aromatic sulfonium salt include triphenylsulfonium hexafluorophosphate, triphenylsulfonium hexafluoroantimonate, diphenyl-4- (phenylthio) phenylsulfonium hexafluorophosphate, diphenyl-4- (phenylthio) phenylsulfonium hexafluoroantimonate, and the like.
Aromatic iodonium salts are salts having an aromatic iodonium as the cationic moiety. Examples of the anion moiety include the same moieties as those of the aromatic sulfonium salt.
Examples of the aromatic iodonium salt include diphenyliodonium hexafluorophosphate, diphenyliodonium hexafluoroantimonate, diphenyliodonium tetrafluoroborate, diphenyliodonium tetrakis (pentafluorophenyl) borate, bis (dodecylphenyl) iodonium hexafluorophosphate, and 4-methylphenyl-4- (1-methylethyl) phenyliodonium hexafluorophosphate.
An aromatic diazonium salt is a salt having an aromatic diazonium as the cationic moiety. Examples of the anion moiety include the same moieties as those of the aromatic sulfonium salt.
Examples of the aromatic diazonium salt include phenyldiazonium hexafluorophosphate, phenyldiazonium hexafluoroantimonate, phenyldiazonium tetrafluoroborate, and phenyldiazonium tetrakis (pentafluorophenyl) borate.
The thioxanthone onium salt is a salt having a thioxanthone onium as a cationic moiety. Examples of the anion moiety include the same moieties as those of the aromatic sulfonium salt.
Examples of the thioxanthone onium salt include S-biphenyl-2-isopropylthioxanthone onium hexafluorophosphate.
The adhesive layer may contain 1 curing catalyst, or2 or more.
When the adhesive layer contains a curing catalyst, the content of the curing catalyst (when 2 or more curing catalysts are contained, the total amount thereof) is not particularly limited, and 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 moisture and heat durability can be formed.
As the silane coupling agent, a known silane coupling agent can be used. Among these, preferred are organosilicon compounds having at least 1 alkoxysilyl group in the molecule.
Examples of the silane coupling agent include silane coupling agents having a (meth) acryloyl group such as 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, 3-methacryloxypropyltriethoxysilane, 3-acryloxypropyltrimethoxysilane and 8-methacryloxyoctyltrimethoxysilane;
silane coupling agents having a vinyl group such as vinyltrimethoxysilane, vinyltriethoxysilane, dimethoxymethylvinylsilane, diethoxymethylvinylsilane, trichloroethylsilane, vinyltris (2-methoxyethoxy) silane, 6-octenyltrimethoxysilane and the like;
silane coupling agents having an epoxy group such as 2- (3, 4-epoxycyclohexyl) ethyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 3-glycidoxypropyltriethoxysilane, and 8-glycidoxypropyloctyltrimethoxysilane;
styrene-based silane coupling agents such as p-styryltrimethoxysilane and p-styryltriethoxysilane;
silane coupling agents having an amino group such as hydrochloride of N- (2-aminoethyl) -3-aminopropylmethyldimethoxysilane, N- (2-aminoethyl) -3-aminopropyltrimethoxysilane, N- (2-aminoethyl) -3-aminopropyltriethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-triethoxysilyl-N- (1, 3-dimethyl spinodal) propylamine, N-phenyl-3-aminopropyltrimethoxysilane, N- (vinylbenzyl) -2-aminoethyl-3-aminopropyltrimethoxysilane, and the like;
silane coupling agents having a ureido group such as 3-ureidopropyltrimethoxysilane and 3-ureidopropyltriethoxysilane;
silane coupling agents having a halogen atom such as 3-chloropropyltrimethoxysilane and 3-chloropropyltriethoxysilane;
silane coupling agents having a mercapto group such as 3-mercaptopropylmethyldimethoxysilane and 3-mercaptopropyltrimethoxysilane;
silane coupling agents having a sulfide group such as bis (trimethoxysilylpropyl) tetrasulfide and bis (triethoxysilylpropyl) tetrasulfide;
silane coupling agents having an isocyanate group such as 3-isocyanatopropyltrimethoxysilane and 3-isocyanatopropyltriethoxysilane;
silane coupling agents having allyl groups such as allyl trichlorosilane, allyl triethoxysilane, and allyl trimethoxysilane;
silane coupling agents having a hydroxyl group such as 3-hydroxypropyltrimethoxysilane and 3-hydroxypropyltriethoxysilane, and the like.
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-methacryloyloxyoctyltrimethoxysilane, 6-octenyltrimethoxysilane, or 8-glycidyloxyoctyltrimethoxysilane, is preferable.
These silane coupling agents may be used alone in 1 kind or in combination of 2 or more kinds.
When the adhesive layer contains a silane coupling agent, the content of the silane coupling agent (the total amount of 2 or more silane coupling agents, if included) 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, and more preferably 0.02 to 5 parts by mass, per 100 parts by mass of the component (a).
When the content of the silane coupling agent is within the above range, a sealant having excellent moist heat durability can be more easily obtained.
(other Components)
The adhesive layer may contain other components within a range not interfering with 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.
These can be used alone in 1 or a combination of 2 or more.
When the adhesive layer contains these additives, the content thereof can be appropriately determined according to the purpose.
(adhesive layer)
The shape, size, and the like of the adhesive layer are not particularly limited. The shape may be a short strip or a long strip. In the present specification, "long" refers to a shape having a length of 5 times or more, preferably 10 times or more, with respect to the width, and specifically refers to a film shape having a length of such an extent that the film shape can be stored or transported while being rolled up. The upper limit of the ratio of the length to the width of the film is not particularly limited, and may be, for example, 100,000 times or less.
The thickness of the adhesive layer is usually 1 to 50 μm, preferably 1 to 25 μm, and more preferably 5 to 25 μm. An adhesive layer having a thickness within the above range can be suitably used as the material for forming the sealing material.
The thickness of the adhesive layer can be measured by a known thickness meter in accordance with JIS K7130 (1999).
The adhesive layer may have a single-layer structure or a multi-layer structure (a structure in which a plurality of adhesive layers are stacked).
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 a multilayer structure, at the interface between two adhesive layers, two components are mixed with each other to form a layer having a single-layer structure in appearance).
The storage elastic modulus of the adhesive layer at 23 ℃ is 5.0X 105Pa or more, preferably 7.0X 105Pa or above. By setting the storage elastic modulus of the adhesive layer at 23 ℃ to 5.0X 105Pa or more, the release film can be peeled without breaking the adhesive layer.
The storage elastic modulus at 23 ℃ is 5.0X 105The adhesive layer having 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, by using a relatively rigid resin such as a phenoxy resin, even when the content of the cyclic ether compound (AL) in the adhesive layer is large, the storage elastic modulus at 23 ℃ is easily obtained to be 5.0 × 105An adhesive layer of Pa or more.
The storage elastic modulus of the adhesive layer at 23 ℃ is 3.0X 107Pa or less, preferably 2.0X 107Pa or less, more preferably 1.5X 107Pa or less. The storage elastic modulus at 23 ℃ is 3.0X 107The adhesive layer having a pressure of Pa or less has sufficient adhesive strength at room temperature, and therefore has excellent adhesion to the object to be sealed at room temperature.
The storage elastic modulus at 23 ℃ is 3.0X 107The adhesive layer of Pa or less can be easily obtained by, for example, increasing the amount of the cyclic ether compound (AL) which is liquid at 25 ℃. In addition, when the adhesive layer contains the thermal cationic polymerization initiator as described above, the cyclic ether compound (a) is a compound having a glycidyl ether group, whereby the storage elastic modulus of the adhesive layer at 23 ℃ can be easily reduced to 3.0 × 107Pa or less.
The storage elastic modulus of the adhesive layer can be measured using a known dynamic viscoelasticity measuring apparatus.
Specifically, the measurement can be carried out by the method described in examples.
The adhesive layer has curability. That is, when the adhesive layer is subjected to a specific curing treatment, the cyclic ether group in the cyclic ether compound (a) reacts, and the adhesive layer is cured to form an adhesive cured layer.
Examples of the curing treatment include a heat treatment and a light irradiation treatment. They may be determined as appropriate depending on the properties of the adhesive layer.
The storage elastic modulus of the adhesive cured layer at 90 ℃ is preferably 1X 108Pa or more, more preferably 1X 109~1×1011Pa. The storage elastic modulus at 90 ℃ is 1X 108The cured adhesive layer having Pa or more is more suitable as a sealing material because of its excellent sealing property. Further, after the adhesive cured layer is formed, in the step of manufacturing the device sealed body, the adhesive cured layer is easily prevented from being broken or peeled.
The storage elastic modulus of the adhesive cured layer can be measured using a known dynamic viscoelasticity measuring apparatus.
Specifically, the measurement can be carried out by the method described in examples.
The cured adhesive layer is excellent in adhesive strength. When a 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/25 mm. The 180 ° peel test can be performed, for example, at a temperature of 23 ℃ and a relative humidity of 50% according to the method for measuring 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 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.
Total light transmittance can be measured according to JIS K7361-1: 1997.
The water vapor transmission rate of the adhesive cured layer is usually 0.1 to 200g-2・day-1Preferably 1 to 150g, seeds and seeds-2・day-1。
The water vapor transmission rate can be measured by using a known gas transmittance measuring device.
[ Release film ]
The adhesive sheet for device sealing of the present invention has a first release film and a second release film.
When the adhesive sheet for sealing a device of the present invention is used, the release film is usually peeled off and removed. At this time, since the peeling force of the second release film is lower, the second release film is peeled off and removed earlier than the first release film.
In the following description, the "first release film" and the "second release film" are sometimes not distinguished from each other, but are abbreviated as "release films".
The release film functions as a support in the production process of 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 thereof 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 substrate for the release film include paper substrates such as cellophane, coated paper, and high-quality paper; laminated paper in which a thermoplastic resin such as polyethylene is laminated on these paper substrates; and plastic films such as polyethylene terephthalate resins, polybutylene terephthalate resins, polyethylene naphthalate resins, polypropylene resins, and polyethylene resins.
Examples of the release agent include rubber elastomers such as silicone resins, olefin resins, isoprene resins, and butadiene resins, long-chain alkyl resins, alkyd resins, and fluorine resins.
The thickness of the release film is not particularly limited, and is usually about 20 to 250 μm.
[ adhesive sheet for sealing device ]
The adhesive sheet for sealing a device of the present invention comprises the first and second release films and the adhesive layer sandwiched between the release films.
The adhesive sheet for sealing a device of the present invention may be a three-layer adhesive sheet of a first release film/an adhesive layer/a second release film.
The method for producing the adhesive sheet for device sealing of the present invention is not particularly limited. For example, the adhesive sheet for device sealing can be manufactured using a casting method.
When the adhesive sheet for device sealing is produced by a casting method, it can be produced by, for example, the following method.
Two sheets of release films (release film (a) and release film (B)) having release layers and a coating liquid containing a component constituting an adhesive layer were prepared. The adhesive layer is formed by applying a coating liquid to the release layer surface of the release film (a) by a known method and drying the resulting coating film. Next, the release film (B) is laminated on the adhesive layer so that the release layer surface of the release film (B) comes into contact with the adhesive layer, whereby an adhesive sheet for device sealing can be obtained.
When the coating liquid is prepared by diluting the components constituting the adhesive layer, 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 alone in 1 kind or in combination of 2 or more kinds.
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.
Examples of the method of drying the coating film by volatilizing the solvent in the coating film include conventionally known drying methods such as hot air drying, hot roll drying, and infrared ray irradiation.
The conditions for drying the coating film are, for example, 80 to 150 ℃ for 30 seconds to 5 minutes, and more preferably 90 to 120 ℃ for 1 minute to 4 minutes. By drying the coating film at 90 ℃ or higher, the coating film can be easily dried even in a drying time of 5 minutes or less, and productivity is excellent.
The adhesive sheet for sealing a device of the present invention satisfies the following formula (1).
[ mathematical formula 2]
x-y≥20 (1)
In the formula, x is a peeling force between the first release film and the adhesive layer (hereinafter sometimes referred to as "first peeling force" in terms of mN/50mm), and y is a peeling force between the second release film and the adhesive layer (hereinafter sometimes referred to as "second peeling force" in terms of mN/50 mm).
When the value of x-y is 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 peeling force is usually 30 to 200mN/50mm, preferably 40 to 150mN/50 mm. 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 the first peeling film is peeled off without peeling the adhesive layer from the adherend, and 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/50 mm.
The first peel force and the second peel force can be measured by the methods described in examples.
The device sealing adhesive sheet satisfying the formula (1) and the device sealing adhesive sheet having the respective peel forces of the first peel force and the second peel force within the above ranges can be efficiently manufactured by appropriately selecting two pieces of the release films based on, for example, the following tendency.
In general, when the release film is thick, the release force tends to be high.
In the above method for producing an adhesive sheet for sealing a facility, the peel strength between the release film (a) to be coated with the coating liquid and the adhesive layer tends to be higher than the peel strength between the release film (B) and the adhesive layer which are superposed after the adhesive layer is formed, even if the same release film is used. Therefore, in such a manufacturing method, in order to increase the difference between the first peeling force and the second peeling force, it is preferable to manufacture the release film (a) using the first peeling film.
In addition, when the release film (B) is heated while being superposed on the adhesive layer, the release force between the release film and the adhesive layer tends to be higher than that in the case of operation at room temperature. Therefore, when the second release film is used as the release film (B), the release film (B) and the adhesive layer are preferably stacked 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 formed of a silicone resin is selected as the two release films, the following tendency is present. As a representative of the silicone-based resin, for example, 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 (corresponding to a crosslinking agent) in 1 molecule can be cited. 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 peeling force of the release film. When a silicone resin is added to an addition reaction type silicone resin, the surface polarity can be adjusted according to the amount of the silicone resin to be added, and the peeling force can be adjusted.
The method for producing the device sealing body using the device sealing adhesive sheet of the present invention is not particularly limited. For example, the device sealing body can be manufactured by performing the following steps (a1) to (a5) and (b1) to (b5) to seal the object to be sealed (device).
Step (a 1): and peeling off the second release film of the device sealing adhesive sheet.
Step (a 2): the adhesive layer exposed by the step (a1) is attached to the object (device) to be sealed.
Step (a 3): the first release film is peeled and removed from the substance obtained in the step (a 2).
Step (a 4): the adhesive layer exposed by the step (a3) is attached to a substrate (glass plate, gas barrier film, etc.).
Step (a 5): the adhesive layer contained in the substance obtained in the step (a4) is cured by a specific means, thereby forming an adhesive cured layer.
Step (b 1): and peeling off the second release film of the device sealing adhesive sheet.
Step (b 2): the adhesive layer exposed by the step (b1) is attached to a substrate (glass plate, gas barrier film, etc.).
Step (b 3): the first release film is peeled and removed from the substance obtained in the step (b 2).
Step (b 4): the adhesive layer exposed by the step (b3) is attached to the object (device) to be sealed.
Step (b 5): the adhesive layer contained in the substance obtained in the step (b4) is cured by a specific means, thereby forming an adhesive cured layer.
In the method for producing the device sealing body, in the step (a2) or the step (b2), the adhesive layer is preferably applied to the object to be sealed or the substrate at room temperature from the viewpoint of ease of operation and productivity. Similarly, the step (b4) is preferably performed at room temperature.
In the adhesive sheet for sealing equipment of the present invention, the release film can be peeled off without breaking the adhesive layer.
Further, the cured adhesive layer formed using the adhesive layer constituting the adhesive sheet for device sealing of the present invention is excellent in adhesive strength and water vapor barrier properties. 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 sealed 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 cured adhesive 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; a material for forming a sealing material in an optical device such as electronic paper.
Examples
The present invention will be described in more detail below with reference to examples. However, the present invention is not limited to the following examples.
In each example, the parts and% are based on mass unless otherwise specified.
[ storage elastic modulus measuring method ]
(1) Storage modulus of elasticity of adhesive layer
The adhesive layer of the adhesive sheet for device sealing obtained in example or comparative example was laminated at 23 ℃ to a thickness of 1mm or more using a laminator, and the obtained laminate was used as a sample for measurement to measure the storage elastic modulus.
That is, the sample for measurement was measured using a storage elastic modulus measuring apparatus (product name: Physica MCR301, manufactured by Anton Paar corporation) under the conditions of a frequency of 1Hz, a strain of 1% and a temperature rise rate of 3 ℃/min, and a storage elastic modulus value of 23 ℃.
(2) Storage elastic modulus of adhesive cured layer
The adhesive layer of the adhesive sheet for device sealing obtained in example or comparative example was laminated at 23 ℃ to a thickness of 200 μm or more using a laminator, and the resulting laminate was heated at 100 ℃ for 1 hour to obtain a cured product thereof. The cured product was used as a sample for measurement, and the storage elastic modulus was measured.
That is, the storage elastic modulus in the temperature range of-20 ℃ to +90 ℃ was measured using a storage elastic modulus measuring apparatus (product name: DMAQ800, manufactured by TA インスツルメント) at a frequency of 11Hz, an amplitude of 5 μm, and a temperature rise rate of 3 ℃/min, and the value of the storage elastic modulus of +90 ℃ was obtained.
[ measurement of peeling force of first and second peeling films ]
The adhesive sheets for machine sealing manufactured in 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 a 180 ° peel test at a peel speed of 300 mm/min under conditions of a temperature of 23 ℃ and a relative humidity of 50%.
That is, the adhesive layer exposed by the second release film of the adhesive sheet for sealing a peeling device was laminated on the alkali-free glass at a temperature of 23 ℃ and a relative humidity of 50%, and after pressure-bonding with a pressure-bonding roller, the above peel test was performed, thereby obtaining the peel force of the first release film. In the following evaluation of breakage of the adhesive layer at the time of peeling of the second release film, regarding the sample evaluated as "B", peeling was carefully performed by hand operation so that transfer of a part of the adhesive layer to the second release film did not occur at the time of peeling of the second release film.
On the other hand, in the peeling test of the second release film, the test piece was obtained in a state where the double-sided tape was attached to the exposed surface of the first release film, and the test piece was attached to the alkali-free glass with the double-sided tape, thereby obtaining a laminate having a layer structure of "alkali-free glass/double-sided tape/first release film/adhesive layer/second release film". Thereafter, the laminate was subjected to a peeling test of the second release film in the same manner as the peeling force of the first release film, and the peeling force was obtained.
[ evaluation of fracture of adhesive layer when peeling off second peeling film ]
In the measurement of the peeling force of the second release film, the state of the adhesive layer after the peeling test was observed to have shifted to the second release film, 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 broke, and part of the adhesive layer was transferred to the second release film.
[ evaluation of suitability of adhesive layer for adhesion to object to be sealed ]
In the measurement of the peeling force of the first release film, the state of the adhesive layer floating from the alkali-free glass was observed before the peeling test was performed, and the case of no floating was referred to as evaluation a and the case of floating was referred to as evaluation B.
[ Compounds and Release films used in examples or comparative examples ]
Seeding of cyclic ether compounds (AL 1): hydrogenated bisphenol A type glycidyl ether epoxy resin (product name: YX8034 manufactured by Mitsubishi ケミカル, liquid at 25 ℃ C., epoxy equivalent: 270g/eq)
Seeding of cyclic ether compounds (AL 2): hydrogenated bisphenol A glycidyl ether epoxy resin (product name: YX8000, liquid at 25 ℃ C., epoxy equivalent: 205g/eq manufactured by Mitsubishi ケミカル Co., Ltd.)
Seeding binder resin (B1): phenoxy resin (trade name: YX7200B35, manufactured by Mitsubishi ケミカル Co., Ltd.; glass transition temperature: 150 ℃ C.)
Seeding curing catalyst (C1): imidazole curing catalyst (product name: キュアゾール 2E4MZ, manufactured by Sichuan chemical industries Co., Ltd.)
Seeding curing catalyst (C2): thermal cationic polymerization initiator (trade name: サンエイド SI-B3, manufactured by Sanxin chemical Co., Ltd.)
Seeding of silane coupling agent (D1): 8-glycidoxy octyl trimethoxysilane (trade name: KBM4803, product of shin-Etsu chemical Co., Ltd.)
Seeding and stripping film (E1): リンテック, trade name: SP-PET752150
Seeding and stripping film (E2): リンテック, trade name: SP-PET381130
Seeding and stripping film (E3): リンテック, trade name: SP-PET751130
Seeding and stripping film (E4): リンテック, trade name: SP-PET 381031.
[ example 1]
100 parts by mass of a binder resin (B1), 250 parts by mass of a cyclic ether compound (AL1), 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 solution was applied to the release-treated surface of a 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 μm. The release-treated surface of a release film (E2) (second release film) was adhered to the adhesive layer to obtain an adhesive sheet for device sealing.
[ example 2]
An adhesive sheet for device sealing was obtained in the same manner as in example 1, except that 130 parts by mass of the cyclic ether compound (AL2) was used in place of the cyclic ether compound (AL1) and 3.8 parts by mass of the curing catalyst (C2) was used in place of the curing catalyst (C1) in example 1.
[ comparative example 1]
An adhesive sheet for device sealing was obtained in the same manner as in example 1, except that 250 parts by mass of the cyclic ether compound (AL2) was used in place of the cyclic ether compound (AL1) and 2 parts by mass of the curing catalyst (C2) was used in place of the curing catalyst (C1) in example 1.
[ comparative example 2]
An adhesive sheet for device sealing was obtained in the same manner as in example 1, except that in example 1, a release film (E3) (first release film) was used in place of the release film (E1) and a release film (E4) (second release film) was used in place of the release film (E2).
[ comparative example 3 ]
An adhesive sheet for device sealing was obtained in the same manner as in example 1, except that 100 parts by mass of the cyclic ether compound (AL2) was used in place of the cyclic ether compound (AL1) and 5 parts by mass of the curing catalyst (C2) was used in place of the curing catalyst (C1) in example 1.
The compositions of the adhesive layers of the adhesive sheets for equipment sealing of examples 1 to 2 and comparative examples 1 to 3 and the test results are shown below.
[ Table 1]
Figure DEST_PATH_IMAGE003
In the adhesive sheets for device sealing of examples 1 and 2, the second release film could be peeled off without breaking the adhesive layer. Further, the adhesive layer of the device sealing adhesive sheet has sufficient adhesive strength at room temperature and is excellent in adhesion suitability.
On the other hand, in the adhesive sheet for device sealing of comparative example 1, the storage elastic modulus of the adhesive layer at 23 ℃ was too low, and therefore, when the second release film was peeled off, the adhesive layer broke.
In the adhesive sheet for device sealing of comparative example 2, the difference in the peeling force between the two peeling films is small, and therefore, the adhesive layer is broken when the second peeling film is peeled.
In the adhesive sheet for device sealing of comparative example 3, the storage elastic modulus of the adhesive layer at 23 ℃ was large, and therefore, even if the difference in the peeling force between the two peeling films was small, the adhesive layer did not break when the second peeling film was peeled. However, the adhesive layer does not have sufficient adhesive strength at room temperature, and the adhesive layer has poor suitability for adhesion.

Claims (10)

1. An adhesive sheet for sealing equipment, 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 following requirements (I) to (III),
requirement (I): the adhesive layer is a layer containing 1 or2 or more compounds having a cyclic ether group;
requirement (II): the adhesive layer has a storage elastic modulus of 5.0 x 10 at 23 DEG C5Pa or more and 3.0X 107Pa below;
requirement (III): when a value of a peeling force between the first release film and the adhesive layer is represented by x (mN/50mm) and a value of a peeling force between the second release film and the adhesive layer is represented by y (mN/50mm), the adhesive sheet for device sealing satisfies the following formula (1):
[ mathematical formula 1]
x-y≥20 (1)。
2. The adhesive sheet for device sealing according to claim 1, wherein at least 1 of the compounds having a cyclic ether group is a compound that is liquid at 25 ℃.
3. The adhesive sheet for device sealing according to claim 2, wherein 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.
4. The adhesive sheet for equipment sealing according to any one of claims 1 to 3, wherein the adhesive layer is a layer further containing a thermal cationic polymerization initiator.
5. The adhesive sheet for device sealing according to claim 4, wherein at least 1 of the compounds having a cyclic ether group is a compound having a glycidyl ether group.
6. The adhesive sheet for equipment sealing according to any one of claims 1 to 5, wherein the adhesive layer is a layer further containing a binder resin.
7. The adhesive sheet for device sealing according to claim 6, wherein the binder resin is a resin having a glass transition temperature of 90 ℃ or higher.
8. The adhesive sheet for device sealing according to any one of claims 1 to 7, wherein a layer obtained by curing the adhesive layer has a storage elastic modulus of 1 x 10 at 90 ℃8Pa or above.
9. The adhesive sheet for sealing equipment according to any one of claims 1 to 8, wherein a value x of a peel force between the first release film and the adhesive layer is 30 to 200mN/50 mm.
10. A method of manufacturing an equipment enclosure, comprising: a step of peeling the second release film from the adhesive sheet for sealing equipment according to any one of claims 1 to 9; and a step of adhering the exposed adhesive layer to the object to be sealed or the substrate in a temperature environment of 20 to 30 ℃.
CN201980040146.XA 2018-06-15 2019-06-14 Adhesive sheet for sealing equipment and method for manufacturing sealing equipment Active CN112368353B (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
JP2018114815 2018-06-15
JP2018-114815 2018-06-15
JP2018-117065 2018-06-20
JP2018117065 2018-06-20
PCT/JP2019/023655 WO2019240261A1 (en) 2018-06-15 2019-06-14 Adhesive sheet for device sealing, and method for manufacturing device seal

Publications (2)

Publication Number Publication Date
CN112368353A true CN112368353A (en) 2021-02-12
CN112368353B CN112368353B (en) 2023-11-28

Family

ID=68841866

Family Applications (2)

Application Number Title Priority Date Filing Date
CN201980040051.8A Active CN112292435B (en) 2018-06-15 2019-06-14 Sealant composition, sealing sheet, and sealing body
CN201980040146.XA Active CN112368353B (en) 2018-06-15 2019-06-14 Adhesive sheet for sealing equipment and method for manufacturing sealing equipment

Family Applications Before (1)

Application Number Title Priority Date Filing Date
CN201980040051.8A Active CN112292435B (en) 2018-06-15 2019-06-14 Sealant composition, sealing sheet, and sealing body

Country Status (5)

Country Link
JP (2) JP7239579B2 (en)
KR (2) KR20210021455A (en)
CN (2) CN112292435B (en)
TW (2) TWI811382B (en)
WO (2) WO2019240260A1 (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP7368202B2 (en) * 2019-11-29 2023-10-24 リンテック株式会社 Sealing sheet
JPWO2021132486A1 (en) * 2019-12-25 2021-07-01
JPWO2023054449A1 (en) * 2021-09-28 2023-04-06
WO2023054677A1 (en) * 2021-09-30 2023-04-06 リンテック株式会社 Curable adhesive sheet, and method for producing cured product

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
WO2014199626A1 (en) 2013-06-10 2014-12-18 三井化学株式会社 Heat-curable composition, surface sealing material for organic el element, and cured object obtained therefrom
JP6829960B2 (en) * 2015-11-27 2021-02-17 日東電工株式会社 Adhesive sheet and adhesive sheet with release film
JP6940224B2 (en) * 2016-09-07 2021-09-22 リンテック株式会社 Gas barrier laminate and seal
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
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

Also Published As

Publication number Publication date
TWI813697B (en) 2023-09-01
KR20210021454A (en) 2021-02-26
JPWO2019240260A1 (en) 2021-07-08
CN112368353B (en) 2023-11-28
JP7303188B2 (en) 2023-07-04
TW202000843A (en) 2020-01-01
CN112292435B (en) 2023-09-01
TWI811382B (en) 2023-08-11
WO2019240261A1 (en) 2019-12-19
CN112292435A (en) 2021-01-29
JP7239579B2 (en) 2023-03-14
TW202000832A (en) 2020-01-01
JPWO2019240261A1 (en) 2021-07-08
KR20210021455A (en) 2021-02-26
WO2019240260A1 (en) 2019-12-19

Similar Documents

Publication Publication Date Title
CN112368353B (en) Adhesive sheet for sealing equipment and method for manufacturing sealing equipment
CN113993958B (en) Adhesive sheet for sealing device
KR102582788B1 (en) Electronic device encapsulation, sheet-like adhesive, adhesive film for electronic device encapsulation, and manufacturing method of electronic device encapsulation
JP6873337B1 (en) Sealing sheet
CN112469800B (en) Curable film-like adhesive and method for producing device
JP7280257B2 (en) Resin composition, encapsulating sheet and encapsulating body
JP7368202B2 (en) Sealing sheet

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant