WO2018092800A1 - 接着剤組成物、封止シート、及び封止体 - Google Patents
接着剤組成物、封止シート、及び封止体 Download PDFInfo
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- WO2018092800A1 WO2018092800A1 PCT/JP2017/041074 JP2017041074W WO2018092800A1 WO 2018092800 A1 WO2018092800 A1 WO 2018092800A1 JP 2017041074 W JP2017041074 W JP 2017041074W WO 2018092800 A1 WO2018092800 A1 WO 2018092800A1
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- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001256 stainless steel alloy Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 1
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- BRKFQVAOMSWFDU-UHFFFAOYSA-M tetraphenylphosphanium;bromide Chemical compound [Br-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BRKFQVAOMSWFDU-UHFFFAOYSA-M 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- GTZCVFVGUGFEME-UHFFFAOYSA-N trans-aconitic acid Natural products OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 description 1
- SGCFZHOZKKQIBU-UHFFFAOYSA-N tributoxy(ethenyl)silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)C=C SGCFZHOZKKQIBU-UHFFFAOYSA-N 0.000 description 1
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- WBTPGJPZNDJHFG-UHFFFAOYSA-N triethoxy-[8-(oxiran-2-ylmethoxy)octyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCCCCCCOCC1CO1 WBTPGJPZNDJHFG-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- MDCWDBMBZLORER-UHFFFAOYSA-N triphenyl borate Chemical compound C=1C=CC=CC=1OB(OC=1C=CC=CC=1)OC1=CC=CC=C1 MDCWDBMBZLORER-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B15/00—Layered products comprising a layer of metal
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B17/00—Layered products essentially comprising sheet glass, or glass, slag, or like fibres
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J123/00—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers
- C09J123/26—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers modified by chemical after-treatment
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J7/00—Adhesives in the form of films or foils
-
- 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
-
- 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
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L31/00—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L31/04—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof adapted as photovoltaic [PV] conversion devices
- H01L31/042—PV modules or arrays of single PV cells
- H01L31/048—Encapsulation of modules
-
- 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
-
- 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
Definitions
- the present invention provides an adhesive composition excellent in moisture barrier properties and adhesive strength, a sealing sheet having an adhesive layer formed using this adhesive composition, and an object to be sealed is sealed with the sealing sheet
- the present invention relates to a sealed body.
- organic EL elements have attracted attention as light emitting elements that can emit light with high luminance by low-voltage direct current drive.
- the organic EL element has a problem that light emission characteristics such as light emission luminance, light emission efficiency, and light emission uniformity are likely to deteriorate with time.
- As a cause of the problem that the light emission characteristic is deteriorated it is conceivable that oxygen, moisture or the like enters the inside of the organic EL element and degrades the electrode or the organic layer.
- several methods using a sealing material have been proposed.
- Patent Document 1 discloses a sheet-like sealing comprising an olefin polymer having a heat of fusion and a weight average molecular weight within a specific range, and a hydrocarbon-based synthetic oil having a kinematic viscosity at 40 ° C. within a specific range. The materials are listed.
- the sheet-like sealing material described in Patent Document 1 has a feature that it can be peeled off as necessary.
- this sheet-shaped sealing material tended to be inferior in adhesive strength.
- the object to be sealed such as an organic EL element is used under severe conditions such as outdoors or in a vehicle. Accordingly, there has been a demand for a sealing sheet that is excellent in adhesive strength in addition to excellent moisture barrier properties and an adhesive composition that is suitably used as a raw material for such a sealing sheet.
- the present invention has been made in view of the above circumstances, and is an adhesive composition excellent in moisture barrier properties and adhesive strength, a sealing sheet having an adhesive layer formed using the adhesive composition, and a cover. It aims at providing the sealing body by which a sealing material is sealed with the said sealing sheet.
- the present inventors have formed an adhesive formed using an adhesive composition containing a modified polyolefin resin, a polyfunctional epoxy compound, a curing accelerator, and a silane coupling agent.
- the layer was found to have excellent moisture barrier properties and adhesive strength, and the present invention was completed.
- the following adhesive compositions [1] to [7], sealing sheets [8] to [11], and sealing bodies [12] and [13] are provided. .
- the following (A) component, (B) component, (C) component, and (D) component (A) component: modified polyolefin resin (B) component: polyfunctional epoxy compound (C) component: curing acceleration Agent (D) component: an adhesive composition containing a silane coupling agent, and when a 180 ° peel test is performed on a test piece obtained using this adhesive composition, the following formula (1)
- the adhesive composition, wherein the x value calculated in (1) is 1.3 or less.
- a represents the adhesive strength obtained by performing a 180 ° peel test under the conditions of a temperature of 23 ° C. and a relative humidity of 50%
- b is a condition of the test piece at a temperature of 60 ° C. and a relative humidity of 90%.
- These 180 ° peel test specimens were obtained by using a sealing sheet composed of an adhesive layer having a thickness of 20 ⁇ m and a polyethylene terephthalate film having a thickness of 50 ⁇ m obtained by using the adhesive composition.
- One side is laminated on a glass plate and laminated under the conditions of a temperature of 60 ° C., a pressure of 0.2 MPa, and a speed of 0.2 m / min (min), and then the obtained crimped body is heated at 100 ° C. for 2 hours. , Obtained by curing the adhesive layer (This is a laminate with a width of 25 mm.)
- a sealing film comprising a release film, a gas barrier film, and an adhesive layer sandwiched between the release film and the gas barrier film, A sealing sheet in which the adhesive layer is formed using the adhesive composition according to any one of [1] to [7].
- a sealed body obtained by sealing an object to be sealed using the sealing sheet according to any one of [8] to [11].
- the sealed body according to [12] wherein the object to be sealed is an organic EL element, an organic EL display element, a liquid crystal display element, or a solar cell element.
- an adhesive composition having excellent moisture barrier properties and adhesive strength a sealing sheet having an adhesive layer formed using this adhesive composition, and an object to be sealed are the sealing sheet.
- a sealed body that is sealed is provided.
- Adhesive composition The adhesive composition of the present invention comprises the following component (A), component (B), component (C), and component (D)
- B) Polyfunctional epoxy compound
- C Polyfunctional epoxy compound
- D Curing accelerator
- (A) component Modified polyolefin-type resin
- the adhesive composition of this invention contains modified polyolefin-type resin as (A) component.
- the adhesive composition of the present invention is excellent in adhesive strength by containing a modified polyolefin resin. Moreover, the adhesive layer of the thickness mentioned later can be efficiently formed by using the adhesive composition containing modified polyolefin resin.
- the modified polyolefin resin is a polyolefin resin having a functional group introduced, which is obtained by subjecting a polyolefin resin as a precursor to a modification treatment using a modifier.
- the polyolefin resin is a polymer containing repeating units derived from olefinic monomers.
- the polyolefin resin may be a polymer composed only of repeating units derived from olefinic monomers, or derived from monomers that are copolymerizable with olefinic monomers and repeating units derived from olefinic monomers. The polymer which consists of these repeating units may be sufficient.
- the olefin monomer is preferably an ⁇ -olefin having 2 to 8 carbon atoms, more preferably ethylene, propylene, 1-butene, isobutylene, 1-pentene, or 1-hexene, and further preferably ethylene or propylene.
- Examples of the monomer copolymerizable with the olefin monomer include vinyl acetate, (meth) acrylic acid, (meth) acrylic acid ester, and styrene.
- (meth) acrylic acid means acrylic acid or methacrylic acid.
- polyolefin resins examples include very low density polyethylene (VLDPE), low density polyethylene (LDPE), medium density polyethylene (MDPE), high density polyethylene (HDPE), linear low density polyethylene (LLDPE), polypropylene (PP), and ethylene.
- VLDPE very low density polyethylene
- LDPE low density polyethylene
- MDPE medium density polyethylene
- HDPE high density polyethylene
- LLDPE linear low density polyethylene
- PP polypropylene
- ethylene -Propylene copolymer
- olefin elastomer TPO
- EVA ethylene-vinyl acetate copolymer
- ethylene- (meth) acrylic acid copolymer ethylene- (meth) acrylic acid ester copolymer, etc. .
- the modifier used for the modification treatment of the polyolefin resin is a compound having a functional group in the molecule, that is, a group that can contribute to a crosslinking reaction described later.
- Functional groups include carboxyl groups, carboxylic anhydride groups, carboxylic ester groups, hydroxyl groups, epoxy groups, amide groups, ammonium groups, nitrile groups, amino groups, imide groups, isocyanate groups, acetyl groups, thiol groups, ether groups. Thioether group, sulfone group, phosphonic acid group, nitro group, urethane group, alkoxysilyl group, silanol group, halogen atom and the like.
- a carboxyl group, a carboxylic acid anhydride group, a carboxylic acid ester group, a hydroxyl group, an ammonium group, an amino group, an imide group, an isocyanate group, and an alkoxysilyl group are preferable, and a carboxylic acid anhydride group and an alkoxysilyl group are more preferable.
- Carboxylic anhydride groups are particularly preferred.
- the compound having a functional group may have two or more kinds of functional groups in the molecule.
- modified polyolefin resin examples include acid-modified polyolefin resins and silane-modified polyolefin resins, and acid-modified polyolefin resins are preferable from the viewpoint of obtaining the better effect of the present invention.
- the acid-modified polyolefin resin is a resin obtained by graft-modifying a polyolefin resin with an acid.
- a polyolefin resin may be reacted with an unsaturated carboxylic acid to introduce a carboxyl group (graft modification).
- the unsaturated carboxylic acid includes the concept of carboxylic acid anhydride.
- the acid-modified polyolefin resin can be obtained, for example, by a method in which an unsaturated carboxylic acid is graft-polymerized to a polyolefin resin in the presence of a radical polymerization initiator such as an organic peroxide or an aliphatic azo compound.
- a radical polymerization initiator such as an organic peroxide or an aliphatic azo compound.
- Examples of the unsaturated carboxylic acid to be reacted with the polyolefin resin include maleic acid, fumaric acid, itaconic acid, citraconic acid, glutaconic acid, tetrahydrophthalic acid, aconitic acid, maleic anhydride, itaconic anhydride, glutaconic anhydride, citraconic anhydride, Examples thereof include aconitic anhydride, norbornene dicarboxylic acid anhydride, and tetrahydrophthalic acid anhydride. These can be used alone or in combination of two or more. Among these, maleic anhydride is preferable because an adhesive composition having better adhesive strength can be easily obtained.
- the amount of the unsaturated carboxylic acid reacted with the polyolefin resin is preferably 0.1 to 5 parts by mass, more preferably 0.2 to 3 parts by mass, and further preferably 0.2 to 3 parts by mass with respect to 100 parts by mass of the polyolefin resin. 1 part by mass.
- the amount of the unsaturated carboxylic acid to be reacted is in the above range, the resulting adhesive composition containing the acid-modified polyolefin resin is superior in adhesive strength.
- Admer registered trademark
- Unistor registered trademark
- BondyRam manufactured by Mitsui Chemicals
- BondyRam manufactured by Polyram
- orevac registered trademark
- Modic registered trademark
- the silane-modified polyolefin resin is obtained by graft-modifying a polyolefin resin with an unsaturated silane compound.
- the silane-modified polyolefin resin has a structure in which an unsaturated silane compound is graft copolymerized with a polyolefin resin.
- a known conventional graft polymerization method may be employed as a condition for graft polymerization of the unsaturated silane compound to the polyolefin resin.
- a method in which a polyolefin resin, an unsaturated silane compound, and a radical generator are melt-mixed at a high temperature and graft polymerization is performed.
- the unsaturated silane compound to be reacted with the polyolefin resin is preferably a vinyl silane compound, such as vinyl trimethoxy silane, vinyl triethoxy silane, vinyl tripropoxy silane, vinyl triisopropoxy silane, vinyl tributoxy silane, vinyl tripentyloxy.
- vinyl silane compound such as vinyl trimethoxy silane, vinyl triethoxy silane, vinyl tripropoxy silane, vinyl triisopropoxy silane, vinyl tributoxy silane, vinyl tripentyloxy.
- Examples include silane, vinyltriphenoxysilane, vinyltribenzyloxysilane, vinyltrimethylenedioxysilane, vinyltriethylenedioxysilane, vinylpropionyloxysilane, vinyltriacetoxysilane, and vinyltricarboxysilane. These can be used alone or in combination of two or more.
- the amount of the unsaturated silane compound to be reacted with the polyolefin resin is preferably 0.1 to 10 parts by mass, more preferably 0.3 to 7 parts by mass with respect to 100 parts by mass of the polyolefin resin. More preferably, it is 0.5 to 5 parts by mass.
- the amount of the unsaturated silane compound to be reacted is within the above range, the resulting adhesive composition containing the silane-modified polyolefin resin is more excellent in adhesive strength.
- silane-modified polyolefin resin examples include a silane-modified polyethylene resin and a silane-modified ethylene-vinyl acetate copolymer.
- silane-modified polyethylene resins such as silane-modified low-density polyethylene, silane-modified linear low-density polyethylene, and silane-modified ultra-low-density polyethylene are preferable.
- silane-modified polyolefin resin Commercially available products can also be used as the silane-modified polyolefin resin.
- Commercially available products include, for example, Linklon (registered trademark) (manufactured by Mitsubishi Chemical Corporation), among others, low density polyethylene-based linklon, linear low-density polyethylene-based linkron, and ultra-low-density polyethylene-based.
- Linklon registered trademark
- the linkron of ethylene-vinyl acetate copolymer system can be preferably used.
- the modified polyolefin resin can be used singly or in combination of two or more.
- the mass average molecular weight (Mw) of the modified polyolefin resin is 10,000 to 2,000,000, preferably 20,000 to 1,500,000.
- the mass average molecular weight (Mn) of the modified polyolefin resin can be determined as a standard polystyrene equivalent value by performing gel permeation chromatography using tetrahydrofuran as a solvent.
- (B) component Multifunctional epoxy compound
- the adhesive composition of this invention contains a polyfunctional epoxy compound as (B) component. Since the polyfunctional epoxy compound reacts with the component (A) to form a crosslinked structure, the cured product of the adhesive composition of the present invention has excellent water vapor barrier properties.
- the polyfunctional epoxy compound refers to a compound having at least two epoxy groups in the molecule.
- epoxy compounds having two or more epoxy groups include bisphenol A diglycidyl ether, bisphenol F diglycidyl ether, bisphenol S diglycidyl ether, brominated bisphenol A diglycidyl ether, brominated bisphenol F diglycidyl ether, and brominated bisphenol S.
- Diglycidyl ether novolac type epoxy resin (for example, phenol novolac type epoxy resin, cresol novolac type epoxy resin, brominated phenol novolac type epoxy resin), hydrogenated bisphenol A diglycidyl ether, hydrogenated bisphenol F diglycidyl ether, Hydrogenated bisphenol S diglycidyl ether, pentaerythritol polyglycidyl ether, 1,6-hexanediol diglycidyl ether, Oxahydrophthalic acid diglycidyl ester, neopentyl glycol diglycidyl ether, trimethylolpropane polyglycidyl ether, 2,2-bis (3-glycidyl-4-glycidyloxyphenyl) propane, dimethyloltricyclodecane diglycidyl ether, etc. Can be mentioned.
- These polyfunctional epoxy compounds can be used singly or in combination of two or more.
- the molecular weight of the polyfunctional epoxy compound is usually 100 to 10,000, preferably 200 to 5,000.
- the epoxy equivalent of the polyfunctional epoxy compound is preferably 100 to 2000 g / eq, more preferably 150 to 1500 g / eq.
- the content of the polyfunctional epoxy compound in the adhesive composition is preferably 10 to 50 parts by mass, more preferably 15 to 40 parts by mass with respect to 100 parts by mass of the component (A).
- a cured product of the adhesive composition in which the content of the polyfunctional epoxy compound is within this range is more excellent in water vapor barrier properties.
- (C) component hardening accelerator
- the adhesive composition of this invention contains a hardening accelerator as (C) component.
- a cured product having excellent adhesiveness can be easily obtained even at high temperatures (for example, 60 ° C.).
- the curing accelerator is not particularly limited as long as it promotes a crosslinking reaction involving a polyfunctional epoxy compound or the like.
- Curing accelerators include imidazole curing accelerators, tertiary amine curing accelerators, phosphine curing accelerators, quaternary ammonium salt curing accelerators, quaternary phosphonium salt curing accelerators, metals A compound type hardening accelerator etc. are mentioned. Among these, an imidazole curing accelerator is preferable from the viewpoint of obtaining a cured product having superior adhesive strength.
- imidazole curing accelerators examples include 2-methylimidazole, 2-phenylimidazole, 2-undecylimidazole, 2-heptadecylimidazole, 2-ethyl-4-methylimidazole, 2-phenyl-4-methylimidazole, 2- Examples include phenyl-4-methyl-5-hydroxymethylimidazole and 2-phenyl-4,5-dihydroxymethylimidazole.
- Tertiary amine curing accelerators include benzyldimethylamine, tris (dimethylaminomethyl) phenol, cyclohexyldimethylamine, triethylamine, 1,8-diaza-bicyclo [5.4.0] undecene-7 (DBU), etc. Is mentioned.
- Examples of the phosphine curing accelerator examples include triphenylphosphine and triphenyl phosphite.
- Examples of the quaternary ammonium salt curing accelerator include tetraethylammonium bromide, tetrabutylammonium bromide, tetraalkylammonium carboxylate, and benzyltriphenylammonium carboxylate.
- Examples of the quaternary phosphonium salt curing accelerator include tetraphenylphosphonium bromide and tetra-n-butylphosphonium bromide.
- Metal compound based curing accelerators include boron trifluoride, triphenylborate, zinc chloride, stannic chloride, aluminum alkoxide, titanium alkoxide, zirconium alkoxide, aluminum tris (acetylacetonate), aluminum tris (ethylacetoacetate) Magnesium bis (acetylacetonate), magnesium bis (ethylacetoacetate), zirconium tetraacetylacetonate, aluminum bisethylacetoacetate / monoacetylacetonate, and the like.
- the content of the curing accelerator in the adhesive composition is preferably 0.1 to 10 parts by mass, more preferably 0.2 to 5 parts by mass with respect to 100 parts by mass of the component (A).
- the cured product of the adhesive composition in which the content of the curing accelerator is within this range has excellent adhesiveness even at high temperatures (for example, 60 ° C.).
- (D) component Silane coupling agent
- the adhesive composition of this invention contains a silane coupling agent as (D) component.
- a silane coupling agent is generally an organosilicon compound having simultaneously a functional group reactively bonded to an organic material and a functional group reactively bonded to an inorganic material (such as a halogen atom or an alkoxy group) in the molecule. It does not specifically limit as a silane coupling agent, A conventionally well-known silane coupling agent can be used. Of these, a silane compound represented by the following formula (2) is preferable from the viewpoint of obtaining a resin composition having more excellent adhesive strength.
- R 1 represents an alkylene group having 3 or more carbon atoms
- R 2 represents a monovalent hydrocarbon group having 1 to 10 carbon atoms
- R 3 represents an alkyl group having 1 to 4 carbon atoms.
- Z represents a group containing a reactive group
- n is 0 or 1.
- the alkylene group represented by R 1 has 3 or more carbon atoms, preferably 3 to 20, and more preferably 4 to 15. When the carbon number of the alkylene group is 3 or more, the crosslinking reaction is more likely to occur.
- Examples of the alkylene group represented by R 1 include trimethylene group, propylene group, tetramethylene group, pentamethylene group, hexamethylene group, heptamethylene group, octamethylene group, nonamethylene group, decamethylene group and the like.
- the monovalent hydrocarbon group represented by R 2 has 1 to 10 carbon atoms, preferably 1 to 6 and more preferably 1 to 4.
- Examples of the monovalent hydrocarbon group represented by R 2 include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, isobutyl group, t-butyl group, and n-pentyl group.
- the alkyl group represented by R 3 has 1 to 4, preferably 1 to 3, more preferably 1 or 2, carbon atoms.
- Examples of the alkyl group represented by R 3 include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, isobutyl group, and t-butyl group.
- Examples of the reactive group contained in Z include an amino group, a hydroxyl group, a thiol group, a vinyl group, an acryloyl group, a methacryloyl group, and an epoxy group, and an epoxy group is preferable.
- Examples of Z containing an epoxy group include an epoxy group, a glycidyl group, and a 3,4-epoxycyclohexyl group.
- silane coupling agent represented by the formula (2) examples include 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 3-glycidoxy Propyltriethoxysilane, 8-glycidoxyoctyltrimethoxysilane, 8-glycidoxyoctyltriethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, 2- (3,4-epoxycyclohexyl) Examples thereof include ethyltriethoxysilane.
- a silane coupling agent can be used individually by 1 type or in combination of 2 or more types.
- the content of the silane coupling agent in the adhesive composition is preferably 0.05 to 5 parts by mass, more preferably 0.1 to 3 parts by mass with respect to 100 parts by mass of the component (A).
- a cured product of the adhesive composition in which the content of the silane coupling agent is within this range has excellent adhesiveness even at high temperatures (for example, 60 ° C.).
- the adhesive composition of the present invention may contain components other than the components (A) to (D).
- Components other than the components (A) to (D) include solvents and various additives.
- Solvents 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; n-pentane, n-hexane, n- And aliphatic hydrocarbon solvents such as heptane; alicyclic hydrocarbon solvents such as cyclopentane, cyclohexane and methylcyclohexane; These solvents can be used alone or in combination of two or more. The amount of the solvent used can be appropriately determined in consideration of coating properties and the like.
- additives include tackifiers, ultraviolet absorbers, antistatic agents, light stabilizers, antioxidants, resin stabilizers, fillers, pigments, extenders, softeners, and the like. These can be used alone or in combination of two or more. When the adhesive composition of this invention contains these additives, the content can be suitably determined according to the objective.
- the adhesive composition of the present invention can be prepared by appropriately mixing and stirring predetermined components according to a conventional method.
- the adhesive composition of the present invention is excellent in moisture barrier properties.
- the water vapor permeability of the layer (adhesive layer after the curing treatment) obtained by curing the adhesive layer formed from the adhesive composition of the present invention is usually 0.1 to 200 g ⁇ m ⁇ 2 ⁇ day. ⁇ 1 , preferably 1 to 150 g ⁇ m ⁇ 2 ⁇ day ⁇ 1 .
- the water vapor transmission rate of the adhesive layer can be measured by a dry / wet sensor method (Lyssy method) described in JIS K 7129: 2008.
- the adhesive composition of the present invention is excellent in adhesive strength.
- the adhesive strength is less likely to be lowered even when placed under high-temperature and high-humidity conditions after bonding.
- the x value calculated by the following formula (1) is 1.3 or less, more preferably 1.2 or less, particularly preferably less than 1.0.
- the lower limit of the x value is preferably 0.6 or more, and more preferably 0.8 or more.
- a represents an adhesive force obtained by performing a 180 ° peel test under the conditions of a temperature of 23 ° C. and a relative humidity of 50%
- b represents a test piece at a temperature of 60 ° C. and a relative humidity of 90%. It was obtained by performing a 180 ° peel test at a temperature of 23 ° C. and a relative humidity of 50% after being allowed to stand for 100 hours under the conditions of, and then at a temperature of 23 ° C. and a relative humidity of 50% for 24 hours. Represents adhesive strength.
- the value of a is usually 1 to 100 N / 25 mm, preferably 10 to 50 N / 25 mm.
- the value of b is usually 1 to 100 N / 25 mm, preferably 10 to 50 N / 25 mm.
- the relationship between the value of a and the value of b is preferably b> a.
- These 180 ° peel test specimens were obtained by using a sealing sheet composed of an adhesive layer having a thickness of 20 ⁇ m and a polyethylene terephthalate film having a thickness of 50 ⁇ m obtained by using the adhesive composition, of the adhesive layer of the sealing sheet.
- the other side is overlaid on the glass plate (so that the surface not adjacent to the polyethylene terephthalate film faces the glass plate), under conditions of a temperature of 60 ° C., a pressure of 0.2 MPa, and a speed of 0.2 m / min. It is a laminate having a width of 25 mm obtained by laminating and then heating the obtained pressure-bonded body at 100 ° C. for 2 hours to cure the adhesive layer.
- the adhesive composition having X of 1.3 or less has a strong interface strength between the adhesive composition and the adherend during bonding, and can prevent water from entering.
- the material of the glass plate used for preparation of the said test piece is not specifically limited, Usually, an alkali free glass is used.
- the thickness is not specifically limited, for example, a 0.7-mm thickness can be used.
- the functional group in component (A) is a reactive group capable of reacting with an epoxy resin, and a carboxylic anhydride group is particularly preferred.
- the epoxy group in (B) component reacts with the reactive group of (A) component, and bridge
- the amount of the component (B) is preferably adjusted so that the epoxy group is 10 to 100 equivalents with respect to the reactive group of the component (A).
- the component (C) is for bringing the adhesive composition and adherend into close contact with each other by being incorporated into the crosslinked structure of the component (A) and the component (B). Therefore, the reactive group of component (C) is preferably a glycidyl group having the same reactivity as component (B).
- the adhesive composition of the present invention is excellent in moisture barrier properties and adhesive strength, the adhesive composition of the present invention is suitably used when forming a sealing material.
- sealing sheet of this invention is the following sealing sheet ((alpha)) or sealing sheet ((beta)).
- Sealing sheet ( ⁇ ) a sealing sheet comprising two release films and an adhesive layer sandwiched between these release films, wherein the adhesive layer uses the adhesive composition of the present invention.
- sealing sheet ( ⁇ ) The release film constituting the sealing sheet ( ⁇ ) functions as a support in the manufacturing process of the sealing sheet ( ⁇ ) and protects the adhesive layer until the sealing sheet ( ⁇ ) is used. Functions as a sheet.
- a conventionally well-known thing can be utilized as a peeling film.
- the substrate for the release film paper substrates such as glassine paper, coated paper, and high-quality paper; laminated paper obtained by laminating a thermoplastic resin such as polyethylene on these paper substrates; polyethylene terephthalate resin, polybutylene terephthalate resin, Examples thereof include plastic films such as polyethylene naphthalate resin, polypropylene resin, and polyethylene resin.
- 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 two release films in the sealing sheet ( ⁇ ) may be the same or different, but the two release films preferably have different release forces.
- the peel strengths of the two release films are different, problems are less likely to occur when the sealing sheet is used. For example, it is possible to more efficiently perform the process of peeling the release film by using two release films having different peel forces and first peeling the peel film having a weak peel force.
- the thickness of the adhesive layer of the sealing sheet ( ⁇ ) is usually 1 to 50 ⁇ m, preferably 5 to 30 ⁇ m.
- An adhesive layer having a thickness within the above range is suitably used as a sealing material.
- a sealing body can be obtained as follows, for example. First, the release film is peeled from the sealing sheet ( ⁇ ) to expose the adhesive layer, and then the exposed adhesive layer is pressure-bonded so as to cover the adherend in an uncured state, and then obtained. The laminated body is heated to a predetermined temperature, and the sealing layer can be obtained by thermosetting the adhesive layer. In the case of further laminating another layer on the obtained sealing body, the remaining release sheet of the sealing sheet ( ⁇ ) is peeled off, and another layer is formed on the exposed adhesive layer. What is necessary is just to laminate. This operation may be performed with the adhesive layer in an uncured state or after it is cured.
- the conditions for pressure-bonding the adhesive layer to the adherend are not particularly limited.
- the temperature is usually 23 to 100 ° C., preferably 40 to 80 ° C.
- the pressure is usually 0.1 to 0.5 MPa, preferably 0.2 to 0.3 MPa.
- the conditions for thermosetting the adhesive layer are not particularly limited.
- the heating temperature is usually 80 to 200 ° C, preferably 90 to 150 ° C.
- the heating time is usually 30 minutes to 12 hours, preferably 1 to 6 hours.
- the adhesive strength is usually 1 to 100 N / 25 mm, preferably 10 to 50 N / 25 mm.
- This 180 ° peel test can be performed according to the method described in the examples.
- the adhesive layer after the curing treatment is excellent in moisture barrier properties.
- the water vapor permeability of the adhesive layer after the curing treatment is usually 0.1 to 200 g ⁇ m ⁇ 2 ⁇ day ⁇ 1 , preferably 1 to 150 g ⁇ m ⁇ 2 ⁇ day ⁇ 1 .
- the water vapor transmission rate of the adhesive layer can be measured by a dry / wet sensor method (Lyssy method) described in JIS K 7129: 2008.
- the manufacturing method of a sealing sheet ((alpha)) is not specifically limited.
- the sealing sheet ( ⁇ ) can be manufactured using a casting method.
- the adhesive composition of the present invention is applied to the release-treated surface of the release film using a known method, and the obtained coating film is dried.
- a sealing sheet ( ⁇ ) can be obtained by producing an adhesive layer with a release film and then stacking another release film on the adhesive layer.
- Examples of the method for applying the adhesive composition include spin coating, spray coating, bar coating, knife coating, roll coating, blade coating, die coating, and gravure coating.
- the drying conditions for drying the coating film include, for example, 80 to 150 ° C. for 30 seconds to 5 minutes.
- the sealing sheet ( ⁇ ) is a sealing sheet comprising a release film, a gas barrier film, and the adhesive film sandwiched between the release film and the gas barrier film, and the adhesive layer is the present invention. It is formed using the adhesive composition of this.
- these sealing sheets represent the state before use, and when using the sealing sheet of this invention, a peeling film is peeled and removed normally.
- the two release films in the sealing sheet ( ⁇ ) may be the same or different, but the two release films preferably have different release forces.
- the peel strengths of the two release films are different, problems are less likely to occur when the sealing sheet is used. For example, if a peeling film having a weak peeling force is peeled first, the step of peeling the peeling film can be performed more efficiently.
- the gas barrier film is not particularly limited as long as it is a film having moisture barrier properties.
- the gas barrier film preferably has a water vapor transmission rate of 0.1 g / m 2 / day or less in an environment of a temperature of 40 ° C. and a relative humidity of 90% (hereinafter abbreviated as “90% RH”). It is more preferable that it is 0.05 g / m 2 / day or less, and it is more preferable that it is 0.005 g / m 2 / day or less.
- the gas barrier film has a water vapor permeability of 0.1 g / m 2 / day or less in an environment of 40 ° C.
- the transmittance of water vapor and the like of the gas barrier film can be measured using a known gas permeability measuring device.
- gas barrier film examples include metal foil, resin film, and thin glass.
- a resin film is preferable, and a gas barrier film having a resin film (base material) and a gas barrier layer is more preferable.
- metal of the metal foil examples include metal materials such as copper, nickel, and aluminum; alloy materials such as stainless steel and aluminum alloys;
- the components and composition of the thin film glass are not particularly limited, but alkali-free borosilicate glass is preferable in terms of obtaining more stable flexibility.
- the thin film glass may be used as a simple substance, or a metal foil such as an aluminum foil or a resin film laminated or laminated on the thin film glass may be used. Further, as the thin film glass, those having a flexibility of about 10 to 200 ⁇ m in thickness are preferable.
- the resin component constituting the base material polyimide, polyamide, polyamideimide, polyphenylene ether, polyether ketone, polyether ether ketone, polyolefin, polyester, polycarbonate, polysulfone, Examples include polyethersulfone, polyphenylene sulfide, polyarylate, acrylic resin, cycloolefin polymer, aromatic polymer, polyurethane polymer, and the like.
- the thickness of the substrate is not particularly limited, but is preferably 0.5 to 500 ⁇ m, more preferably 1 to 200 ⁇ m, and further preferably 5 to 100 ⁇ m from the viewpoint of ease of handling.
- the material of the gas barrier layer is not particularly limited as long as a desired gas barrier property can be imparted.
- the gas barrier layer include an inorganic film and a layer obtained by subjecting a layer containing a polymer compound to a modification treatment.
- the gas barrier layer is preferably a gas barrier layer made of an inorganic film and a gas barrier layer obtained by implanting ions into a layer containing a polymer compound because a layer having a small thickness and excellent gas barrier properties can be efficiently formed. .
- the inorganic film is not particularly limited, and examples thereof include an inorganic vapor deposition film.
- the inorganic vapor deposition film include vapor deposition films of inorganic compounds and metals.
- the raw material for the vapor-deposited film of the inorganic compound inorganic oxides such as silicon oxide, aluminum oxide, magnesium oxide, zinc oxide, indium oxide and tin oxide; inorganic nitrides such as silicon nitride, aluminum nitride and titanium nitride; inorganic carbides; Inorganic sulfides; inorganic oxynitrides such as silicon oxynitride; inorganic oxide carbides; inorganic nitride carbides; inorganic oxynitride carbides and the like.
- the raw material for the metal vapor deposition film include aluminum, magnesium, zinc, and tin.
- Examples of the method for forming the inorganic film include a vacuum vapor deposition method, an EB vapor deposition method, a sputtering method, an ion plating method, a laminate method, a plasma vapor deposition method (CVD method), and the like.
- the thickness of the inorganic film is appropriately selected depending on the type and configuration of the inorganic material, but is usually 1 to 500, and preferably 2 to 300 nm.
- the polymer compound used is a silicon-containing polymer such as polyorganosiloxane or polysilazane compound.
- a silicon-containing polymer such as polyorganosiloxane or polysilazane compound.
- These polymer compounds can be used alone or in combination of two or more.
- silicon-containing polymer compounds are preferable, and polysilazane compounds are more preferable.
- the polysilazane compound is a polymer compound having a repeating unit containing —Si—N— bond (silazane bond) in the molecule. Specifically, the formula (3)
- the compound which has a repeating unit represented by these is preferable.
- the number average molecular weight of the polysilazane compound to be used is not particularly limited, but is preferably 100 to 50,000.
- Rx, Ry, and Rz each independently represent a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted cycloalkyl group, an unsubstituted or substituted alkenyl group, unsubstituted or substituted Represents a non-hydrolyzable group such as an aryl group having a group or an alkylsilyl group;
- Rx, Ry, and Rz a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group is preferable, and a hydrogen atom is particularly preferable.
- Examples of the polysilazane compound having a repeating unit represented by the formula (3) include inorganic polysilazanes in which Rx, Ry, and Rz are all hydrogen atoms, and organic polysilazanes in which at least one of Rx, Ry, and Rz is not a hydrogen atom. It may be.
- Polysilazane compounds can be used singly or in combination of two or more.
- a modified polysilazane compound can also be used as the polysilazane compound.
- a commercially available product as a glass coating material or the like can be used as it is.
- the polymer layer may contain other components in addition to the above-described polymer compound as long as the object of the present invention is not impaired.
- other components include curing agents, other polymers, anti-aging agents, light stabilizers, and flame retardants.
- the content of the polymer compound in the polymer layer is preferably 50% by mass or more and more preferably 70% by mass or more because a gas barrier layer having better gas barrier properties can be obtained.
- the thickness of the polymer layer is not particularly limited, but is preferably in the range of 50 to 300 nm, more preferably 50 to 200 nm. In the present invention, a sealing sheet having a sufficient gas barrier property can be obtained even if the thickness of the polymer layer is nano-order.
- a layer forming solution containing at least one polymer compound, optionally other components, a solvent, and the like is used as a known method such as a spin coater, a knife coater, a gravure coater, or the like.
- a method in which an apparatus is used for coating and the resulting coating film is appropriately dried to form is used as a known method.
- Examples of the polymer layer modification treatment include ion implantation treatment, plasma treatment, ultraviolet irradiation treatment, and heat treatment.
- the ion implantation process is a method of modifying the polymer layer by implanting ions into the polymer layer, as will be described later.
- the plasma treatment is a method for modifying the polymer layer by exposing the polymer layer to plasma.
- plasma treatment can be performed according to the method described in Japanese Patent Application Laid-Open No. 2012-106421.
- the ultraviolet irradiation treatment is a method for modifying the polymer layer by irradiating the polymer layer with ultraviolet rays.
- the ultraviolet modification treatment can be performed according to the method described in JP2013-226757A.
- the ion implantation treatment is preferable because the gas barrier layer can be efficiently modified to the inside without roughening the surface of the polymer layer and more excellent in gas barrier properties.
- ions implanted into the polymer layer ions of rare gases such as argon, helium, neon, krypton, and xenon; ions such as fluorocarbon, hydrogen, nitrogen, oxygen, carbon dioxide, chlorine, fluorine, and sulfur; Ions of alkane gases such as methane and ethane; Ions of alkene gases such as ethylene and propylene; Ions of alkadiene gases such as pentadiene and butadiene; Ions of alkyne gases such as acetylene; Benzene, toluene, etc.
- rare gases such as argon, helium, neon, krypton, and xenon
- ions such as fluorocarbon, hydrogen, nitrogen, oxygen, carbon dioxide, chlorine, fluorine, and sulfur ions of alkane gases such as methane and ethane
- Ions of alkene gases such as ethylene and propylene
- Ions of alkadiene gases such
- Ions of aromatic hydrocarbon gases such as: ions of cycloalkane gases such as cyclopropane; ions of cycloalkene gases such as cyclopentene; ions of metals; ions of organosilicon compounds; These ions can be used alone or in combination of two or more.
- ions of rare gases such as argon, helium, neon, krypton, and xenon are preferable because ions can be more easily implanted and a gas barrier layer having particularly excellent gas barrier properties can be obtained.
- the method for implanting ions is not particularly limited. For example, there are a method of irradiating ions accelerated by an electric field (ion beam), a method of injecting ions in plasma (ion of plasma generation gas), etc., and a gas barrier layer can be easily obtained.
- a method of implanting ions is preferred.
- plasma is generated in an atmosphere containing a plasma generation gas, and a negative high voltage pulse is applied to a layer into which ions are implanted, whereby ions (positive ions) in the plasma are ionized. Can be performed by injecting into the surface portion of the layer to be injected.
- the gas barrier film may be one in which a primer layer is provided between the base material and the gas barrier layer.
- a primer layer is provided between the base material and the gas barrier layer.
- a photopolymerizable composition comprising a silicon-containing compound; a photopolymerizable compound comprising a photopolymerizable monomer and / or a photopolymerizable prepolymer, and a polymerization initiator that generates radicals at least in the visible light region; Resin, polyurethane resin (especially two-part curable resin of polyacryl polyol, polyester polyol, polyether polyol, etc.
- the primer layer as the method for applying the primer layer forming solution, and the method for drying and heating the obtained coating film, those described above as the method for forming the polymer layer can be used.
- the thickness of the primer layer is usually 10 to 1000 nm.
- the manufacturing method of a sealing sheet ((beta)) is not specifically limited.
- the sealing sheet ( ⁇ ) can be manufactured by replacing one of the release films with a gas barrier film.
- the sealing sheet ((beta)) is manufactured by peeling the one peeling film and sticking the exposed adhesive bond layer and a gas-barrier film. You can also.
- the sealing sheet ( ⁇ ) has two release films having different release forces, it is preferable to release the release film having the smaller release force from the viewpoint of handleability.
- the adhesive layer of the sealing sheet of the present invention is excellent in adhesive strength and moisture barrier properties. For this reason, the deterioration can be efficiently suppressed by sealing an organic EL element using the sealing sheet of this invention.
- the sealing body of the present invention is such that an object to be sealed is sealed using the sealing sheet of the present invention.
- “It is sealed using the sealing sheet of the present invention” means that the release film constituting the sealing sheet of the present invention is removed to expose the adhesive layer, and the adhesive layer is sealed. This means that the object to be sealed is covered with the material.
- the sealing body of the present invention includes, for example, a transparent substrate, an element (an object to be sealed) formed on the transparent substrate, and a sealing material for sealing the element. The sealing material is sealed with the adhesive layer of the sealing sheet ( ⁇ ) or ( ⁇ ) of the present invention.
- the layer structure of the sealing body of the present invention include the following, but are not limited to the following. In addition, in the following, it describes in the aspect which peeled and removed the peeling film.
- transparent substrate / element (sealed object) formed on the transparent substrate / adhesive layer ii) transparent substrate / element (sealed object) formed on the transparent substrate / adhesive layer / Gas barrier layer (iii) transparent substrate / element (sealed material) formed on the transparent substrate / adhesive layer / gas barrier layer / base film
- the transparent substrate is not particularly limited, and various substrate materials can be used. In particular, it is preferable to use a substrate material having a high visible light transmittance. In addition, a material having a high blocking performance for blocking moisture and gas to enter from the outside of the element and having excellent solvent resistance and weather resistance is preferable.
- transparent inorganic materials such as quartz and glass; polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polystyrene, polyethylene, polypropylene, polyphenylene sulfide, polyvinylidene fluoride, acetyl cellulose, brominated phenoxy, aramids, polyimides, Examples thereof include transparent plastics such as polystyrenes, polyarylates, polysulfones, and polyolefins, and the gas barrier film described above.
- the thickness of the transparent substrate is not particularly limited, and can be appropriately selected in consideration of light transmittance and performance for blocking the inside and outside of the element.
- Examples of the objects to be sealed include organic EL elements, organic EL display elements, liquid crystal display elements, solar cell elements, and the like.
- the manufacturing method of the sealing body of this invention is not specifically limited. For example, after the adhesive layer of the sealing sheet of the present invention is stacked on the object to be sealed, the adhesive layer of the sealing sheet and the object to be sealed are bonded by heating. Subsequently, the sealing body of this invention can be manufactured by hardening this adhesive bond layer.
- the conditions described above can be used as the curing conditions when the adhesive layer of the sealing sheet and the object to be sealed are adhered and when the adhesive layer is cured.
- the sealing body of the present invention is formed by sealing an object to be sealed with the sealing sheet of the present invention. Therefore, in the sealed body of the present invention, the performance of the object to be sealed is maintained for a long time.
- Acid-modified polyolefin resin (1) Modified ⁇ -olefin polymer, mass average molecular weight: 52,000, manufactured by Mitsui Chemicals, Inc., trade name: UNISTOL H-200
- Polyfunctional epoxy compound (1) Hydrogenated bisphenol A diglycidyl ether, manufactured by Kyoeisha Chemical Co., Ltd., trade name: Epolite 4000, molecular weight: 470, epoxy equivalent: 235 g / eq
- Polyfunctional epoxy compound (2) dimethylol tricyclodecane diglycidyl ether, manufactured by ADEKA Corporation, trade name: Adeka Resin, EP-4088L, molecular weight: 330, epoxy equivalent: 165 g / eq
- Polyfunctional epoxy compound (3) hydrogenated bisphenol A diglycidyl ether, manufactured by Mitsubishi Chemical Corporation, trade name: jER YX8034, molecular weight: 540, epoxy equivalent: 270 g / eq I
- Example 1 Methyl ethyl ketone containing 100 parts of acid-modified polyolefin resin (1), 25 parts of polyfunctional epoxy compound (1), 0.25 part of imidazole curing accelerator (1), and 0.1 part of silane coupling agent (1) It melt
- the adhesive composition (1) was applied onto the release-treated surface of a release film (product name: SP-PET382150, manufactured by Lintec Corporation), and the resulting coating film was dried at 100 ° C. for 2 minutes to obtain a thickness. A 20 ⁇ m adhesive layer was formed, and the release-treated surface of another release film (manufactured by Lintec Corporation, trade name: SP-PET381031) was bonded thereon to obtain a sealing sheet (1).
- Example 2 In Example 1, it replaced with the polyfunctional epoxy compound (1), and except having used the polyfunctional epoxy compound (2), it carried out similarly to Example 1, and obtained the sealing sheet (2).
- Example 3 In Example 1, it replaced with the polyfunctional epoxy compound (1), and except having used the polyfunctional epoxy compound (3), it carried out similarly to Example 1, and obtained the sealing sheet (3).
- Example 4 In Example 1, it replaced with the silane coupling agent (1), and except having used the silane coupling agent (2), it carried out similarly to Example 1, and obtained the sealing sheet (4).
- Example 1 the sealing sheet (5) was obtained like Example 1 except the point which does not use a silane coupling agent.
- Example 2 the sealing sheet (6) was obtained like Example 2 except the point which does not use a silane coupling agent.
- Example 3 the sealing sheet (7) was obtained like Example 1 except the point which does not use a polyfunctional epoxy compound and an imidazole series curing catalyst.
- the obtained pressure-bonded body was heated at 100 ° C. for 2 hours to cure the adhesive layer, and two test pieces were obtained.
- Adhesion measurement As a peel test (a), the test piece was subjected to a 180 ° peel test under the conditions of a temperature of 23 ° C. and a relative humidity of 50%.
- a 180 ° peel test was conducted under the conditions of 50 ° C. and 50% relative humidity. In this peeling test, the test was performed according to the method for measuring adhesive strength described in JIS Z0237: 2000 except for the test conditions described above.
- An organic EL element having a glass substrate on which an indium tin oxide (ITO) film (thickness: 100 nm, sheet resistance: 50 ⁇ / ⁇ : ohms per square) was formed as an anode was produced by the following method.
- ITO indium tin oxide
- N, N′-bis (naphthalen-1-yl) -N, N′-bis (phenyl) -benzidine) made by Luminescence Technology 50 nm
- Tris (8- Hydroxy-quinolinate) aluminum manufactured by Luminescence Technology was sequentially deposited at a rate of 50 nm and a rate of 0.1 to 0.2 nm / min to form a light emitting layer.
- lithium fluoride (LiF) manufactured by High-Purity Chemical Laboratory
- Al aluminum
- the cathode was formed by vapor-depositing 100 nm at a rate of 0.1 nm / min to obtain an organic EL device.
- the degree of vacuum at the time of vapor deposition was 1 ⁇ 10 ⁇ 4 Pa or less.
- One release film of the sealing sheet obtained in Examples or Comparative Examples was peeled off, and the exposed adhesive layer was stacked on the metal foil film, and these were adhered at 60 ° C. using a heat laminator.
- another release film was peeled off, and the exposed adhesive layer was layered so as to cover the organic EL element formed on the glass substrate, and these were adhered at 60 ° C. using a heat laminator.
- the electronic device was allowed to stand for 250 hours in an environment of a temperature of 60 ° C.
- ⁇ Dark spot is less than 40% of light emission area
- ⁇ Dark spot is 40% or more and less than 50% of light emission area
- ⁇ Dark spot is 50% or more of light emission area
- Table 1 shows the following.
- the sealing sheets of Examples 1 to 4 maintain excellent adhesive strength even after standing at high temperature and high humidity (60 ° C., relative humidity 90%, standing for 100 hours), and have excellent sealing properties. Yes.
- the sealing sheets of Comparative Examples 1 to 3 are placed under high temperature and high humidity conditions (60 ° C., 90% relative humidity, left standing for 100 hours), the adhesive strength is greatly reduced, and the sealing properties are poor. Yes.
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Abstract
Description
しかし、有機EL素子には、時間の経過とともに、発光輝度、発光効率、発光均一性等の発光特性が低下し易いという問題があった。
この発光特性が低下する問題の原因として、酸素や水分等が有機EL素子の内部に浸入し、電極や有機層を劣化させることが考えられる。
そして、この対処方法として、封止材を用いる方法がいくつか提案されている。例えば、特許文献1には、融解熱量と重量平均分子量が特定の範囲内にあるオレフィン重合体と、40℃における動粘度が特定の範囲内にある炭化水素系合成油とを含むシート状封止材が記載されている。
有機EL素子等の被封止物には、屋外や車内等の過酷な条件で使用される場合も多い。従って、優れた水分遮断性に加えて、接着強度にも優れる封止シートや、このような封止シートの原料として好適に用いられる接着剤組成物が要望されていた。
〔1〕下記の(A)成分、(B)成分、(C)成分、及び(D)成分
(A)成分:変性ポリオレフィン系樹脂
(B)成分:多官能エポキシ化合物
(C)成分:硬化促進剤
(D)成分:シランカップリング剤
を含有する接着剤組成物であって、この接着剤組成物を用いて得られた試験片について180°剥離試験を行ったときに、下記式(1)で算出されるx値が、1.3以下であることを特徴とする接着剤組成物。
〔3〕前記(B)成分の含有量が、前記(A)成分100質量部に対して10~50質量部である、〔1〕又は〔2〕に記載の接着剤組成物。
〔4〕前記(C)成分が、イミダゾール系硬化促進剤である、〔1〕~〔3〕のいずれかに記載の接着剤組成物。
〔5〕前記(C)成分の含有量が、前記(A)成分100質量部に対して0.1~10質量部である、〔1〕~〔4〕のいずれかに記載の接着剤組成物。
〔6〕前記(D)成分が、下記式(2)で示される化合物である、〔1〕~〔5〕のいずれかに記載の接着剤組成物。
〔7〕前記(D)成分の含有量が、前記(A)成分100質量部に対して0.05~5質量部である、〔1〕~〔6〕のいずれかに記載の接着剤組成物。
〔8〕2枚の剥離フィルムと、これらの剥離フィルムに挟持された接着剤層とからなる封止シートであって、前記接着剤層が、〔1〕~〔7〕のいずれかに記載の接着剤組成物を用いて形成されたものである封止シート。
〔9〕剥離フィルム、ガスバリア性フィルム、及び、前記剥離フィルムとガスバリア性フィルムに挟持された接着剤層からなる封止シートであって、
前記接着剤層が、〔1〕~〔7〕のいずれかに記載の接着剤組成物を用いて形成されたものである封止シート。
〔10〕前記ガスバリア性フィルムが、金属箔、樹脂製フィルム、又は薄膜ガラスである〔9〕に記載の封止シート。
〔11〕接着剤層の厚みが1~50μmである、〔8〕~〔10〕のいずれかに記載の封止シート。
〔12〕被封止物が、〔8〕~〔11〕のいずれかに記載の封止シートを用いて封止されてなる封止体。
〔13〕前記被封止物が、有機EL素子、有機ELディスプレイ素子、液晶ディスプレイ素子、又は太陽電池素子である、〔12〕に記載の封止体。
本発明の接着剤組成物は、下記の(A)成分、(B)成分、(C)成分、及び(D)成分
(A)成分:変性ポリオレフィン系樹脂
(B)成分:多官能エポキシ化合物
(C)成分:硬化促進剤
(D)成分:シランカップリング剤
を含有する接着剤組成物であって、上記式(1)で算出されるX値が、1.3以下であることを特徴とする。
本発明の接着剤組成物は、(A)成分として、変性ポリオレフィン系樹脂を含有する。
本発明の接着剤組成物は、変性ポリオレフィン系樹脂を含有することで、接着強度に優れたものとなる。また、変性ポリオレフィン系樹脂を含有する接着剤組成物を用いることで、後述する厚みの接着剤層を効率よく形成することができる。
オレフィン系単量体と共重合可能な単量体としては、酢酸ビニル、(メタ)アクリル酸、(メタ)アクリル酸エステル、スチレン等が挙げられる。ここで、(メタ)アクリル酸とは、アクリル酸又はメタクリル酸を意味する。
官能基としては、カルボキシル基、カルボン酸無水物基、カルボン酸エステル基、水酸基、エポキシ基、アミド基、アンモニウム基、ニトリル基、アミノ基、イミド基、イソシアネート基、アセチル基、チオール基、エーテル基、チオエーテル基、スルホン基、ホスホン酸基、ニトロ基、ウレタン基、アルコキシシリル基、シラノール基、ハロゲン原子等が挙げられる。これらの中でも、カルボキシル基、カルボン酸無水物基、カルボン酸エステル基、水酸基、アンモニウム基、アミノ基、イミド基、イソシアネート基、アルコキシシリル基が好ましく、カルボン酸無水物基、アルコキシシリル基がより好ましく、カルボン酸無水物基が特に好ましい。
官能基を有する化合物は、分子内に2種以上の官能基を有していてもよい。
これらは、1種を単独で、あるいは2種以上を組み合わせて用いることができる。これらの中でも、接着強度により優れる接着剤組成物が得られ易いことから、無水マレイン酸が好ましい。
変性ポリオレフィン系樹脂の質量平均分子量(Mn)は、テトラヒドロフランを溶媒として用いてゲルパーミエーションクロマトグラフィーを行い、標準ポリスチレン換算値として求めることができる。
本発明の接着剤組成物は、(B)成分として、多官能エポキシ化合物を含有する。
多官能エポキシ化合物は、(A)成分と反応して架橋構造を形成するものであるため、本発明の接着剤組成物の硬化物は水蒸気遮断性に優れる。
エポキシ基を2つ以上有するエポキシ化合物としては、ビスフェノールAジグリシジルエーテル、ビスフェノールFジグリシジルエーテル、ビスフェノールSジグリシジルエーテル、臭素化ビスフェノールAジグリシジルエーテル、臭素化ビスフェノールFジグリシジルエーテル、臭素化ビスフェノールSジグリシジルエーテル、ノボラック型エポキシ樹脂(例えばフェノール・ノボラック型エポキシ樹脂、クレゾール・ノボラック型エポキシ樹脂、臭素化フェノール・ノボラック型エポキシ樹脂)、水添ビスフェノールAジグリシジルエーテル、水添ビスフェノールFジグリシジルエーテル、水添ビスフェノールSジグリシジルエーテル、ペンタエリスリトールポリグリシジルエーテル、1,6-ヘキサンジオールジグリシジルエーテル、ヘキサヒドロフタル酸ジグリシジルエステル、ネオペンチルグリコールジグリシジルエーテル、トリメチロールプロパンポリグリシジルエーテル、2,2-ビス(3-グリシジル-4-グリシジルオキシフェニル)プロパン、ジメチロールトリシクロデカンジグリシジルエーテル等が挙げられる。
これらの多官能エポキシ化合物は、1種単独で、あるいは2種以上を組み合わせて用いることができる。
多官能エポキシ化合物のエポキシ当量は、好ましくは100~2000g/eq、より好ましくは150~1500g/eqである。
本発明の接着剤組成物は、(C)成分として、硬化促進剤を含有する。
硬化促進剤を含有する接着剤組成物を用いることで、高温時(例えば、60℃)においても優れた接着性を有する硬化物が得られ易くなる。
硬化促進剤は、多官能エポキシ化合物等が関与する架橋反応を促進するものであれば特に限定されない。
これらの中でも、より優れた接着強度を有する硬化物が得られる観点から、イミダゾール系硬化促進剤が好ましい。
第3級アミン系硬化促進剤としては、ベンジルジメチルアミン、トリス(ジメチルアミノメチル)フェノール、シクロヘキシルジメチルアミン、トリエチルアミン及び1,8-ジアザ-ビシクロ[5.4.0]ウンデセン-7(DBU)等が挙げられる。
ホスフィン系硬化促進剤としては、トリフェニルホスフィン、亜リン酸トリフェニル等が挙げられる。
第4級ホスホニウム塩系硬化促進剤としては、テトラフェニルホスホニウムブロマイド、テトラ-n-ブチルホスホニウムブロマイド等が挙げられる。
金属化合物系硬化促進剤としては、三フッ化ホウ素、トリフェニルボレート、塩化亜鉛、塩化第二錫、アルミニウムアルコキシド、チタンアルコキシド、ジルコニウムアルコキシド、アルミニウムトリス(アセチルアセトネート)、アルミニウムトリス(エチルアセトアセテート)、マグネシウムビス(アセチルアセトネート)、マグネシウムビス(エチルアセトアセテート)、ジルコニウムテトラアセチルアセトナート、アルミニウムビスエチルアセトアセテート・モノアセチルアセトネート等が挙げられる。
接着剤組成物中の硬化促進剤の含有量は、前記(A)成分100質量部に対して、好ましくは0.1~10質量部、より好ましくは0.2~5質量部である。
硬化促進剤の含有量がこの範囲内にある接着剤組成物の硬化物は、高温時(例えば、60℃)においても優れた接着性を有する。
本発明の接着剤組成物は、(D)成分として、シランカップリング剤を含有する。
シランカップリング剤を含有する接着剤組成物を用いることで、常温(通常、20~30℃)及び高温高湿環境(例えば、60℃、相対湿度90%)下における接着性により優れた硬化物が得られ易くなる。
アルキレン基の炭素数が3以上であることで、架橋反応がより起こり易くなる。
R1で表されるアルキレン基としては、トリメチレン基、プロピレン基、テトラメチレン基、ペンタメチレン基、ヘキサメチレン基、ヘプタメチレン基、オクタメチレン基、ノナメチレン基、デカメチレン基等が挙げられる。
R2で表される1価の炭化水素基としては、メチル基、エチル基、n-プロピル基、イソプロピル基、n-ブチル基、sec-ブチル基、イソブチル基、t-ブチル基、n-ペンチル基、n-ヘキシル基、n-ヘプチル基、n-オクチル基、n-ノニル基、n-デシル基等のアルキル基;ビニル基、1-プロペニル基、2-プロペニル基、イソプロペニル基、3-ブテニル基、4-ペンテニル基、5-ヘキセニル基等のアルケニル基;エチニル基、プロパルギル基、ブチニル基等のアルキニル基;フェニル基、1-ナフチル基、2-ナフチル基等のアリール基;等が挙げられる。
R3で表されるアルキル基としては、メチル基、エチル基、n-プロピル基、イソプロピル基、n-ブチル基、sec-ブチル基、イソブチル基、t-ブチル基が挙げられる。
エポキシ基を含有するZとしては、エポキシ基、グリシジル基、3,4-エポキシシクロヘキシル基等が挙げられる。
接着剤組成物中のシランカップリング剤の含有量は、前記(A)成分100質量部に対して、好ましくは0.05~5質量部、より好ましくは0.1~3質量部である。
シランカップリング剤の含有量がこの範囲内にある接着剤組成物の硬化物は、高温時(例えば、60℃)においても優れた接着性を有する。
(A)~(D)成分以外の成分としては、溶媒、各種添加剤が挙げられる。
溶媒としては、ベンゼン、トルエン等の芳香族炭化水素系溶媒;酢酸エチル、酢酸ブチル等のエステル系溶媒;アセトン、メチルエチルケトン、メチルイソブチルケトン等のケトン系溶媒;n-ペンタン、n-ヘキサン、n-ヘプタン等の脂肪族炭化水素系溶媒;シクロペンタン、シクロヘキサン、メチルシクロヘキサン等の脂環式炭化水素系溶媒;等が挙げられる。
これらの溶媒は、1種単独で、あるいは2種以上を組み合わせて用いることができる。
溶媒の使用量は、塗工性等を考慮して適宜決定することができる。
これらは1種単独で、あるいは2種以上を組み合わせて用いることができる。
本発明の接着剤組成物がこれらの添加剤を含有する場合、その含有量は、目的に合わせて適宜決定することができる。
接着剤層の水蒸気透過率は、JIS K 7129:2008記載の乾湿センサー法(Lyssy法)にて測定することができる。
例えば、本発明の接着剤組成物を用いて得られた試験片について180°剥離試験を行ったときに、下記式(1)で算出されるx値が1.3以下であり、より好ましくは1.2以下であり、特に好ましくは1.0未満である。x値の下限は0.6以上が好ましく0.8以上がより好ましい。
bの値は、通常、1~100N/25mm、好ましくは10~50N/25mmである。
aの値とbの値の関係は、b>aであることが好ましい。
Xが1.3以下の接着剤組成物は、接着時に接着剤組成物と被着体の界面強度が強く、水の浸入を防ぐことができる。
前記試験片の作製に用いるガラス板の材質は特に限定されないが、通常、無アルカリガラスを用いる。また、その厚みも特に限定されないが、例えば、0.7mm厚のものを使用することができる。
(A)成分中の官能基はエポキシ樹脂と反応可能な反応性基で、特にカルボン酸無水物基が好ましい。
また、(B)成分中のエポキシ基は、(A)成分の反応性基と反応して架橋することで強固な構造を形成する。従って、(A)成分の反応性基に対して十分な量のエポキシ基が必要となる。具体的には、(A)成分の反応性基に対してエポキシ基が10~100当量になるように(B)成分の量を調整することが好ましい。
(C)成分は、(A)成分と(B)成分の架橋構造中に取り込まれることによって、接着剤組成物と被着体を強く密着させるものである。従って、(C)成分の反応性基は(B)成分と同様の反応性を持つグリシジル基であることが好ましい。
本発明の封止シートは、下記の封止シート(α)又は封止シート(β)である。
封止シート(α):2枚の剥離フィルムと、これらの剥離フィルムに挟持された接着剤層とからなる封止シートであって、前記接着剤層が、本発明の接着剤組成物を用いて形成されたものであることを特徴とするもの
封止シート(β):剥離フィルムと、ガスバリア性フィルムと、前記剥離フィルムと前記ガスバリア性フィルムに挟持された接着剤層とからなる封止シートであって、前記接着剤層が、本発明の接着剤組成物を用いて形成されたものであることを特徴とするもの
なお、これらの封止シートは使用前の状態を表したものであり、本発明の封止シートを使用する際は、通常、剥離フィルムは剥離除去される。
封止シート(α)を構成する剥離フィルムは、封止シート(α)の製造工程においては支持体として機能するとともに、封止シート(α)を使用するまでの間は、接着剤層の保護シートとして機能する。
剥離フィルム用の基材としては、グラシン紙、コート紙、上質紙等の紙基材;これらの紙基材にポリエチレン等の熱可塑性樹脂をラミネートしたラミネート紙;ポリエチレンテレフタレート樹脂、ポリブチレンテレフタレート樹脂、ポリエチレンナフタレート樹脂、ポリプロピレン樹脂、ポリエチレン樹脂等のプラスチックフィルム;等が挙げられる。
剥離剤としては、シリコーン系樹脂、オレフィン系樹脂、イソプレン系樹脂、ブタジエン系樹脂等のゴム系エラストマー、長鎖アルキル系樹脂、アルキド系樹脂、フッ素系樹脂等が挙げられる。
封止シート(α)を使用する場合、例えば、次のようにして封止体を得ることができる。まず、封止シート(α)から剥離フィルムを剥離して、接着剤層を露出させ、次いで、露出した接着剤層を未硬化の状態で被着体を覆うように圧着させ、その後、得られた積層物を所定温度に加熱して、前記接着剤層を熱硬化させることで封止体を得ることができる。
なお、得られた封止体上に別の層を更に積層する場合には、前記封止シート(α)の残された剥離シートを剥離して、露出した接着剤層上に別の層を積層させればよい。この操作は、接着剤層が未硬化の状態で実施しても、硬化させた後に実施してもよい。
温度は、通常、23~100℃、好ましくは40~80℃である。
圧力は、通常、0.1~0.5MPa、好ましくは0.2~0.3MPaである。
加熱温度は、通常、80~200℃、好ましくは90~150℃である。
加熱時間は、通常、30分から12時間、好ましくは1~6時間である。
また、硬化処理後の接着剤層は水分遮断性に優れる。硬化処理後の接着剤層の水蒸気透過率は、通常、0.1~200g・m-2・day-1、好ましくは1~150g・m-2・day-1である。
接着剤層の水蒸気透過率は、JIS K 7129:2008記載の乾湿センサー法(Lyssy法)にて測定することができる。
封止シート(α)をキャスト法により製造する場合、公知の方法を用いて、本発明の接着剤組成物を剥離フィルムの剥離処理面に塗工し、得られた塗膜を乾燥することで、剥離フィルム付接着剤層を製造し、次いで、もう1枚の剥離フィルムを接着剤層上に重ねることで、封止シート(α)を得ることができる。
塗膜を乾燥するときの乾燥条件としては、例えば80~150℃で30秒~5分間が挙げられる。
封止シート(β)は、剥離フィルムと、ガスバリア性フィルムと、前記剥離フィルムと前記ガスバリア性フィルムに挟持された接着剤層とからなる封止シートであって、前記接着剤層が、本発明の接着剤組成物を用いて形成されたものであることを特徴とする。
なお、これらの封止シートは使用前の状態を表したものであり、本発明の封止シートを使用する際は、通常、剥離フィルムは剥離除去される。
ガスバリア性フィルムは、温度40℃、相対湿度90%(以下、「90%RH」と略記する。)の環境下における水蒸気透過率が0.1g/m2/day以下であることが好ましく、0.05g/m2/day以下であることがより好ましく、0.005g/m2/day以下であることがさらに好ましい。
ガスバリア性フィルムの温度40℃、90%RHの環境下における水蒸気透過率が0.1g/m2/day以下であることで、透明基板上に形成された有機EL素子等の素子内部に酸素や水分等が浸入し、電極や有機層が劣化することを効果的に抑制することができる。
ガスバリア性フィルムの水蒸気等の透過率は、公知のガス透過率測定装置を使用して測定することができる。
薄膜ガラスは、薄膜ガラスを単体として用いてもよいが、アルミ箔等の金属箔や樹脂フィルムを、薄膜ガラスに積層あるいはラミネートしたものを用いてもよい。
また、薄膜ガラスとしては、厚みが10~200μm程度のフレキシブル性を有するものが好ましい。
基材の厚みは、特に制限はないが、取り扱い易さの観点から、好ましくは0.5~500μm、より好ましくは1~200μm、さらに好ましくは5~100μmである。
無機蒸着膜としては、無機化合物や金属の蒸着膜が挙げられる。
無機化合物の蒸着膜の原料としては、酸化珪素、酸化アルミニウム、酸化マグネシウム、酸化亜鉛、酸化インジウム、酸化スズ等の無機酸化物;窒化ケイ素、窒化アルミニウム、窒化チタン等の無機窒化物;無機炭化物;無機硫化物;酸化窒化ケイ素等の無機酸化窒化物;無機酸化炭化物;無機窒化炭化物;無機酸化窒化炭化物等が挙げられる。
金属の蒸着膜の原料としては、アルミニウム、マグネシウム、亜鉛、及びスズ等が挙げられる。
無機膜の厚みは、無機材料の種類や構成により適宜選択されるが、通常、1~500であり、好ましくは、2~300nmである。
これらの中でも、優れたガスバリア性を有するガスバリア層を形成できる観点から、ケイ素含有高分子化合物が好ましく、ポリシラザン系化合物がより好ましい。
Rx、Ry、Rzは、それぞれ独立して、水素原子、無置換若しくは置換基を有するアルキル基、無置換若しくは置換基を有するシクロアルキル基、無置換若しくは置換基を有するアルケニル基、無置換若しくは置換基を有するアリール基又はアルキルシリル基等の非加水分解性基を表す。これらの中でも、Rx、Ry、Rzとしては、水素原子、炭素数1~6のアルキル基、又はフェニル基が好ましく、水素原子が特に好ましい。前記式(3)で表される繰り返し単位を有するポリシラザン系化合物としては、Rx、Ry、Rzが全て水素原子である無機ポリシラザン、Rx、Ry、Rzの少なくとも1つが水素原子ではない有機ポリシラザンのいずれであってもよい。
高分子層中の高分子化合物の含有量は、より優れたガスバリア性を有するガスバリア層が得られることから、50質量%以上が好ましく、70質量%以上がより好ましい。
本発明においては、高分子層の厚みがナノオーダーであっても、充分なガスバリア性を有する封止シートを得ることができる。
イオン注入処理は、後述するように、高分子層にイオンを注入して、高分子層を改質する方法である。
プラズマ処理は、高分子層をプラズマ中に晒して、高分子層を改質する方法である。例えば、特開2012-106421号公報に記載の方法に従って、プラズマ処理を行うことができる。
紫外線照射処理は、高分子層に紫外線を照射して高分子層を改質する方法である。例えば、特開2013-226757号公報に記載の方法に従って、紫外線改質処理を行うことができる。
これらの中でも、高分子層の表面を荒らすことなく、その内部まで効率よく改質し、よりガスバリア性に優れるガスバリア層を形成できることから、イオン注入処理が好ましい。
メタン、エタン等のアルカン系ガス類のイオン;エチレン、プロピレン等のアルケン系ガス類のイオン;ペンタジエン、ブタジエン等のアルカジエン系ガス類のイオン;アセチレン等のアルキン系ガス類のイオン;ベンゼン、トルエン等の芳香族炭化水素系ガス類のイオン;シクロプロパン等のシクロアルカン系ガス類のイオン;シクロペンテン等のシクロアルケン系ガス類のイオン;金属のイオン;有機ケイ素化合物のイオン;等が挙げられる。
これらのイオンは1種単独で、あるいは2種以上を組み合わせて用いることができる。
これらの中でも、より簡便にイオンを注入することができ、特に優れたガスバリア性を有するガスバリア層が得られることから、アルゴン、ヘリウム、ネオン、クリプトン、キセノン等の希ガスのイオンが好ましい。
プライマー層は、プライマー層形成用溶液の塗布方法、及び得られた塗膜の乾燥、加熱方法としては、それぞれ、高分子層を形成する方法として先に示したものを用いることができる。プライマー層を形成する場合、プライマー層の厚みは、通常、10~1000nmである。
また、封止シート(α)を製造した後、その1枚の剥離フィルムを剥離し、露出した接着剤層とガスバリア性フィルムとを貼着することにより、封止シート(β)を製造することもできる。この場合、封止シート(α)が、異なる剥離力を有する2枚の剥離フィルムを有する場合には、取扱い性の観点から、剥離力の小さい方の剥離フィルムを剥離するのが好ましい。
本発明の封止体は、被封止物が、本発明の封止シートを用いて封止されてなるものである。
「本発明の封止シートを用いて封止されてなる」とは、本発明の封止シートを構成する剥離フィルムを除去して接着剤層を露出させ、その接着剤層を被封止物に密着させて、被封止物を覆うことをいう。
本発明の封止体としては、例えば、透明基板と、該透明基板上に形成された素子(被封止物)と、該素子を封止するための封止材とを備えるものであって、前記封止材が、本発明の封止シート(α)又は(β)の接着剤層により封止されてなるものが挙げられる。
(i)透明基板/該透明基板上に形成された素子(被封止物)/接着剤層
(ii)透明基板/該透明基板上に形成された素子(被封止物)/接着剤層/ガスバリア層
(iii)透明基板/該透明基板上に形成された素子(被封止物)/接着剤層/ガスバリア層/基材フィルム
(iv)透明基板/該透明基板上に形成された素子(被封止物)/接着剤層/ガスバリア層/プライマー層/基材フィルム
透明基板の厚みは特に制限されず、光の透過率や、素子内外を遮断する性能を勘案して、適宜選択することができる。
次いで、この接着剤層を硬化させることにより、本発明の封止体を製造することができる。
したがって、本発明の封止体においては、長期にわたって被封止物の性能が維持される。
各例中の部及び%は、特に断りのない限り、質量基準である。
酸変性ポリオレフィン系樹脂(1):変性α-オレフィン重合体、質量平均分子量:52,000、三井化学株式会社製、商品名:ユニストールH-200
多官能エポキシ化合物(1):水添ビスフェノールAジグリシジルエーテル、共栄社化学株式会社製、商品名:エポライト4000、分子量:470、エポキシ当量:235g/eq
多官能エポキシ化合物(2):ジメチロールトリシクロデカンジグリシジルエーテル、株式会社ADEKA製、商品名:アデカレジン、EP-4088L、分子量:330、エポキシ当量:165g/eq
多官能エポキシ化合物(3):水添ビスフェノールAジグリシジルエーテル、三菱化学株式会社製、商品名:jER YX8034、分子量:540、エポキシ当量:270g/eq
イミダゾール系硬化促進剤(1):2-エチル-4-メチルイミダゾール、四国化成株式会社製、商品名:キュアゾール2E4MZ
シランカップリング剤(1):8-グリシドキシオクチルトリメトキシシラン、信越化学工業株式会社製、商品名:KBM4803
シランカップリング剤(2):3-グリシドキシプロピルトリメトキシシラン、信越化学工業株式会社製、商品名:KBM403
酸変性ポリオレフィン系樹脂(1)100部、多官能エポキシ化合物(1)25部、イミダゾール系硬化促進剤(1)0.25部、及び、シランカップリング剤(1)0.1部をメチルエチルケトンに溶解し、固形分濃度18%の接着剤組成物(1)を調製した。
この接着剤組成物(1)を剥離フィルム(リンテック株式会社製、商品名:SP-PET382150)の剥離処理面上に塗工し、得られた塗膜を100℃で2分間乾燥し、厚みが20μmの接着剤層を形成し、その上に、もう1枚の剥離フィルム(リンテック株式会社製、商品名:SP-PET381031)の剥離処理面を貼り合わせて封止シート(1)を得た。
実施例1において、多官能エポキシ化合物(1)に代えて、多官能エポキシ化合物(2)を使用したことを除き、実施例1と同様にして封止シート(2)を得た。
実施例1において、多官能エポキシ化合物(1)に代えて、多官能エポキシ化合物(3)を使用したことを除き、実施例1と同様にして封止シート(3)を得た。
実施例1において、シランカップリング剤(1)に代えて、シランカップリング剤(2)を使用したことを除き、実施例1と同様にして封止シート(4)を得た。
実施例1において、シランカップリング剤を使用しない点を除き、実施例1と同様にして封止シート(5)を得た。
実施例2において、シランカップリング剤を使用しない点を除き、実施例2と同様にして封止シート(6)を得た。
実施例1において、多官能エポキシ化合物とイミダゾール系硬化触媒を使用しない点を除き、実施例1と同様にして封止シート(7)を得た。
〔試験片の作製〕
幅が25mmの封止シートの剥離フィルムを1枚剥がして露出させた接着剤層を、厚みが50μm、幅が25mmのポリエチレンテレフタレートフィルム(東洋紡株式会社製、商品名「コスモシャイン PET50A4300)に重ねた。次いで、もう1枚の剥離フィルムを剥がして露出させた接着剤層をガラス板に重ねて、温度60℃、圧力0.2MPa、速度0.2m/分の条件でラミネートして圧着体を得た。得られた圧着体を100℃で2時間加熱して、その接着剤層を硬化させ、試験片をそれぞれ2枚ずつ得た。
〔接着力測定〕
剥離試験(a)として、試験片を、温度23℃、相対湿度50%の条件下で180°剥離試験を行った。
剥離試験(b)として、試験片を、温度60℃、相対湿度90%の条件下に100時間、次いで、温度23℃、相対湿度50%の条件下に24時間静置させた後に、温度23℃、相対湿度50%条件下で180°剥離試験を行った。
この剥離試験において、上述した試験条件以外は、JIS Z0237:2000に記載の粘着力の測定方法に準じて行った。
酸化インジウムスズ(ITO)膜(厚み:100nm、シート抵抗:50Ω/□:ohms per square)が成膜されたガラス基板を陽極として有する有機EL素子を、以下の方法により作製した。
まず、前記ガラス基板のITO膜上に、N,N’-ビス(ナフタレン-1-イル)-N,N’-ビス(フェニル)-ベンジジン)(Luminescence Technology社製)を50nm、トリス(8-ヒドロキシ-キノリネート)アルミニウム(Luminescence Technology社製)を50nm、0.1~0.2nm/分の速度で順次蒸着させ、発光層を形成した。
得られた発光層上に、電子注入材料として、フッ化リチウム(LiF)(高純度化学研究所社製)を0.1nm/分の速度で4nm、次いでアルミニウム(Al)(高純度化学研究所社製)を0.1nm/分の速度で100nm蒸着させて陰極を形成し、有機EL素子を得た。
なお、蒸着時の真空度は、全て1×10-4Pa以下であった。
この電子デバイスを、温度60℃、相対湿度90%の環境下に250時間静置させた後、有機EL素子を起動させ、ダークスポット(非発光箇所)の有無を観察し、以下の基準で評価した。
◎:ダークスポットが発光面積の40%未満
○:ダークスポットが発光面積の40%以上50%未満
×:ダークスポットが発光面積の50%以上
実施例1~4の封止シートは、高温高湿条件静置(60℃、相対湿度90%、100時間静置)後においても優れた接着強度が維持され、また、封止性に優れている。
一方、比較例1~3の封止シートは、高温高湿条件に置く(60℃、相対湿度90%、100時間静置)と、接着強度が大きく低下し、また、封止性に劣っている。
Claims (13)
- 下記の(A)成分、(B)成分、(C)成分、及び(D)成分
(A)成分:変性ポリオレフィン系樹脂
(B)成分:多官能エポキシ化合物
(C)成分:硬化促進剤
(D)成分:シランカップリング剤
を含有する接着剤組成物であって、この接着剤組成物を用いて得られた試験片について180°剥離試験を行ったときに、下記式(1)で算出されるx値が、1.3以下であることを特徴とする接着剤組成物。
- 前記(A)成分が、酸変性ポリオレフィン系樹脂である、請求項1に記載の接着剤組成物。
- 前記(B)成分の含有量が、前記(A)成分100質量部に対して10~50質量部である、請求項1又は2に記載の接着剤組成物。
- 前記(C)成分が、イミダゾール系硬化促進剤である、請求項1~3のいずれかに記載の接着剤組成物。
- 前記(C)成分の含有量が、前記(A)成分100質量部に対して0.1~10質量部である、請求項1~4のいずれかに記載の接着剤組成物。
- 前記(D)成分の含有量が、前記(A)成分100質量部に対して0.05~5質量部である、請求項1~6のいずれかに記載の接着剤組成物。
- 2枚の剥離フィルムと、これらの剥離フィルムに挟持された接着剤層とからなる封止シートであって、
前記接着剤層が、請求項1~7のいずれかに記載の接着剤組成物を用いて形成されたものである封止シート。 - 剥離フィルム、ガスバリア性フィルム、及び、前記剥離フィルムとガスバリア性フィルムに挟持された接着剤層からなる封止シートであって、
前記接着剤層が、請求項1~7のいずれかに記載の接着剤組成物を用いて形成されたものである封止シート。 - 前記ガスバリア性フィルムが、金属箔、樹脂製フィルム、又は薄膜ガラスである請求項9に記載の封止シート。
- 接着剤層の厚みが1~50μmである、請求項8~10のいずれかに記載の封止シート。
- 被封止物が、請求項8~11のいずれかに記載の封止シートを用いて封止されてなる封止体。
- 前記被封止物が、有機EL素子、有機ELディスプレイ素子、液晶ディスプレイ素子、又は太陽電池素子である、請求項12に記載の封止体。
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JPWO2018092800A1 (ja) | 2019-10-17 |
KR102380827B1 (ko) | 2022-03-30 |
CN109890926A (zh) | 2019-06-14 |
TWI781964B (zh) | 2022-11-01 |
TW201831634A (zh) | 2018-09-01 |
KR20190084962A (ko) | 2019-07-17 |
CN109890926B (zh) | 2021-12-28 |
JP7071279B2 (ja) | 2022-05-18 |
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