WO2016158770A1 - 封止用樹脂組成物 - Google Patents

封止用樹脂組成物 Download PDF

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Publication number
WO2016158770A1
WO2016158770A1 PCT/JP2016/059664 JP2016059664W WO2016158770A1 WO 2016158770 A1 WO2016158770 A1 WO 2016158770A1 JP 2016059664 W JP2016059664 W JP 2016059664W WO 2016158770 A1 WO2016158770 A1 WO 2016158770A1
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WIPO (PCT)
Prior art keywords
resin
sealing
resin composition
modified
copolymer
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PCT/JP2016/059664
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English (en)
French (fr)
Japanese (ja)
Inventor
舞 高瀬
有希 山本
達也 本間
中嶋　聡
英治 馬場
賢 大橋
Original Assignee
味の素株式会社
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Application filed by 味の素株式会社 filed Critical 味の素株式会社
Priority to CN201680016320.3A priority Critical patent/CN107406639B/zh
Priority to JP2017509913A priority patent/JP6680295B2/ja
Priority to KR1020177030477A priority patent/KR102522727B1/ko
Publication of WO2016158770A1 publication Critical patent/WO2016158770A1/ja

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Classifications

    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00—Compositions of unspecified macromolecular compounds
    • C08L101/12—Compositions of unspecified macromolecular compounds characterised by physical features, e.g. anisotropy, viscosity or electrical conductivity
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C08L23/04—Homopolymers or copolymers of ethene
    • C08L23/08—Copolymers of ethene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C08L23/04—Homopolymers or copolymers of ethene
    • C08L23/08—Copolymers of ethene
    • C08L23/0846—Copolymers of ethene with unsaturated hydrocarbons containing other atoms than carbon or hydrogen atoms
    • C08L23/0869—Acids or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • C08L23/26—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers modified by chemical after-treatment
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of 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
    • 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
    • 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
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2203/00—Applications
    • C08L2203/16—Applications used for films
    • C08L2203/162—Applications used for films sealable films

Definitions

  • the present invention relates to an encapsulating resin composition, an encapsulating sheet, and the like, and more particularly to an encapsulating resin composition and an encapsulating sheet that can be suitably used for encapsulating an organic EL element.
  • An organic EL (Electroluminescence) element is a light-emitting element using an organic substance as a light-emitting material, and has been attracting attention in recent years because it can emit light with high luminance at a low voltage.
  • the organic EL element is extremely vulnerable to moisture, and the organic material itself is altered by moisture, resulting in a decrease in brightness, no light emission, or the interface between the electrode and the organic EL layer being peeled off due to moisture, Since there is a problem that the metal is oxidized to increase the resistance, the organic EL element is sealed.
  • thermosetting resin composition When the thermosetting resin composition is used as a sealing material for the entire surface of a substrate having an organic EL element, the laminating work is easy because the material viscosity before curing is low, and the permeation resistance of the cured product after thermosetting is low. An advantage is high wetness. However, on the other hand, there is a problem that the organic EL element deteriorates due to the heating temperature during thermosetting.
  • Patent Document 1 discloses sealing with a polyisobutylene resin, a polyisoprene resin having a functional group capable of reacting with an epoxy group and / or a polyisobutylene resin, a tackifying resin, and a resin composition containing an epoxy resin.
  • Patent Document 2 discloses a technique of sealing with a resin composition containing a styrene-isobutylene-modified resin and a tackifier resin.
  • the problem to be solved by the present invention is to provide a sealing resin composition excellent in adhesion wet heat resistance and moisture permeability resistance.
  • the present inventor has (A) (meth) acrylic acid alkyl ester and polyolefin-based resin modified with acid anhydride, (B) epoxy resin, and (C) tackifying resin.
  • a sealing resin composition characterized by containing a pressure-sensitive adhesive composition having a good cross-linking structure formed by heating before sealing, and having excellent resistance to moisture and heat resistance and moisture permeability.
  • the headline and the present invention were completed.
  • a sealing resin comprising (A) a (meth) acrylic acid alkyl ester and a polyolefin-based resin modified with an acid anhydride, (B) an epoxy resin, and (C) a tackifying resin. Composition.
  • (A) An ester bond formed by reacting an acid anhydride group of a polyolefin resin modified with (meth) acrylic acid alkyl ester and acid anhydride and an epoxy group of (B) epoxy resin is formed.
  • a sealing sheet. [12] The sealing sheet according to [11], which is used for sealing an organic EL element.
  • a resin varnish containing the sealing resin composition according to any one of the above [1] to [9] is applied onto a support and heat-dried, and (A) an alkyl (meth) acrylate Production of a sealing sheet, wherein an acid anhydride group of a polyolefin-based resin modified with an ester and an acid anhydride and an epoxy group of (B) an epoxy resin are ester-bonded by reaction to form an adhesive layer Method.
  • the sealing resin composition excellent in the adhesion heat-and-moisture resistance and moisture permeability resistance, the sealing sheet obtained from it, and the organic EL device sealed with this sealing resin composition are provided. Is done.
  • the encapsulating resin composition of the present invention (hereinafter also simply referred to as “resin composition”) is (A) a polyolefin-based resin modified with (meth) acrylic acid alkyl ester and acid anhydride, and (B) epoxy.
  • resin composition is (A) a polyolefin-based resin modified with (meth) acrylic acid alkyl ester and acid anhydride, and (B) epoxy.
  • the main feature is that it contains a resin and (C) a tackifying resin.
  • the resin composition of the present invention includes a polyolefin resin modified with a (meth) acrylic acid alkyl ester and an acid anhydride (hereinafter sometimes referred to as “modified polyolefin resin” or “(A) component”). Is used.
  • the polyolefin resin of the main skeleton of the modified polyolefin resin used in the present invention is not particularly limited as long as it has a skeleton derived from an olefin monomer.
  • a polyethylene resin, a polypropylene resin, a polybutene resin, a polyisobutylene resin, and the like can be given.
  • polyethylene resins, polypropylene resins, and polybutene resins are preferable, and polyethylene resins and polypropylene resins are particularly preferable.
  • the polyethylene-based resin referred to here is a homopolymer of ethylene or a main monomer unit (a monomer unit of more than 50% by mass) made of ethylene. At least ethylene and a unit other than ethylene are used. It means a copolymer containing a monomer unit (for example, a monomer unit such as an olefin excluding ethylene, a non-conjugated diene, an alkyl (meth) acrylate), and the polypropylene resin is a homopolymer of propylene, Alternatively, the main monomer unit (a monomer unit of more than 50% by mass) is composed of propylene, at least propylene and monomer units other than propylene (for example, olefins other than propylene, non-conjugated dienes, (meth)
  • a polybutene-based resin is a homopolymer of butene, or Is a main monomer unit (a monomer unit of more than 50% by mass) consisting
  • a monomer unit other than isobutylene eg, a monomer unit such as an olefin excluding isobutylene, a non-conjugated diene, or a (meth) acrylic acid alkyl ester.
  • the polyethylene resin is superior to the polypropylene resin.
  • “processability” refers to processability particularly when a modified polyolefin resin is formed on a film (layer), and the fluidity of the resin varnish to enable film (layer) formation (time-lapse). Stability) and the like.
  • polypropylene resin is superior to polyethylene resin.
  • the copolymer includes (i) a copolymer of two or more olefins, (ii) a copolymer of olefin and non-conjugated diene, or (iii) a monomer other than olefin such as olefin and styrene (non-conjugated diene). And a copolymer thereof.
  • the olefin can use 1 type (s) or 2 or more types.
  • copolymer in the polyolefin resin examples include, for example, ethylene-nonconjugated diene copolymer, ethylene- (meth) acrylic acid alkyl ester copolymer, ethylene-butene copolymer, ethylene-butene-nonconjugated.
  • any copolymer may be a random copolymer or a block copolymer.
  • the block copolymer may be a diblock copolymer or a triblock copolymer.
  • an ethylene-butene copolymer block copolymer is a diblock copolymer (polyethylene block (polyethylene skeleton) -polybutene block (polybutene skeleton)) consisting of a multi-block consisting of alternating repeating polyethylene blocks and polybutene blocks.
  • Block copolymer polyethylene block (polyethylene skeleton) -polybutene block (polybutene skeleton) -triblock copolymer consisting of polyethylene block (polyethylene skeleton), polybutene block (polybutene skeleton) -polyethylene block (polyethylene skeleton)- A triblock copolymer comprising a polybutene block (polybutene skeleton) is included. The same applies to binary copolymers other than ethylene-butene copolymers.
  • polyethylene resin for example, ethylene-propylene copolymer, ethylene-butene copolymer, ethylene-propylene-butene copolymer and the like can be used from the viewpoint of improving heat resistance and the like.
  • propylene-based resin for example, from the viewpoint of improving processability and embedding property, a propylene-ethylene copolymer, a propylene-butene copolymer, and an ethylene-propylene-butene copolymer can be used. Further, from the viewpoint of improving heat resistance, a propylene-butene copolymer can be used.
  • the butene used in the present invention is not particularly limited, and can include 1-butene, cis-2-butene, trans-2-butene, isobutene (other name: 2-methylpropene), and the like. Two or more types can be used in combination, but 1-butene is preferred.
  • the ethylene-butene copolymer may be a copolymer obtained by copolymerizing ethylene and two or more types of butene, or the butene units are different from each other. It may be a mixture of two or more ethylene-butene copolymers comprising butene.
  • the form of the ethylene-butene copolymer is not particularly limited, and may be a random copolymer or a block copolymer. Among them, from the viewpoint of improving processability, the random copolymer is used. Polymers are preferred.
  • olefins that may be included as monomer units of polyolefin resins (that is, olefins other than ethylene, propylene, butene, and isobutylene) include 1-pentene, 3-methyl-1-hexene, 3-methyl ⁇ having 2 to 11 carbon atoms, such as -1-pentene, 4-methyl-1-pentene, 3-ethyl-1-pentene, 1-septene, 1-octene, 1-nonene, 1-decene, 1-undecene, etc. Mention may be made of olefins (excluding propylene and 1-butene). Of these, 1-hexene is preferable. Such ⁇ -olefins can be used alone or in combination of two or more.
  • olefins having a carbon number such as methylhexadiene (2-methyl-1,5-hexadiene, 3-methyl-2,4-hexadiene, etc.), 1,9-decadiene, 1,13-tetradecadiene, etc.
  • methylhexadiene is preferable, and 2-methyl-1,5-hexadiene is particularly preferable.
  • non-conjugated diolefin compounds can be used alone or in combination of two or more.
  • a copolymer of olefin and (meth) acrylic acid alkyl ester can be used as the polyolefin resin of the main skeleton in the modified polyolefin resin of the present invention.
  • (meth) acrylic acid alkyl ester means acrylic acid alkyl ester and methacrylic acid alkyl ester. Either one or both of acrylic acid alkyl ester and methacrylic acid alkyl ester may be used.
  • the alkyl group in the (meth) acrylic acid alkyl ester may be an unsubstituted alkyl group or a substituted alkyl group (for example, an aralkyl group), but an unsubstituted alkyl group is preferred.
  • the group preferably has 1 to 20 carbon atoms, more preferably 1 to 10 carbon atoms.
  • (meth) acrylic acid alkyl esters include, for example, methyl acrylate, ethyl acrylate, butyl acrylate, ethyl hexyl acrylate, isobutyl acrylate, benzyl acrylate, phenoxyethyl acrylate, methyl methacrylate, methacrylic acid Examples include ethyl, butyl methacrylate, ethyl hexyl methacrylate, isobutyl methacrylate, benzyl methacrylate, and phenoxyethyl methacrylate. Of these, methyl methacrylate is preferred.
  • One or more (meth) acrylic acid alkyl esters can be used.
  • a copolymer containing at least butene as a monomer unit such as an ethylene-butene copolymer, an isobutylene-butene copolymer, and a propylene-butene copolymer
  • ethylene-butene copolymer an ethylene-butene copolymer
  • isobutylene-butene copolymer an isobutylene-butene copolymer
  • a propylene-butene copolymer is a resin composition.
  • the content of ethylene units is preferably 20% by mass or more based on the whole copolymer, 30 mass% or more is more preferable, 40 mass% or more is still more preferable, and 50 mass% or more is the most preferable.
  • 95% by mass or less is preferable, and 90% by mass or less is more preferable.
  • ethylene- (meth) acrylic acid alkyl ester copolymer In the modified polyolefin resin of the present invention, ethylene- (meth) acrylic acid alkyl ester copolymer, isobutylene- (meth) acrylic acid alkyl ester copolymer, propylene- (meth) acrylic acid alkyl ester copolymer, etc.
  • the copolymer of olefin and (meth) acrylic acid alkyl ester which contains at least (meth) acrylic acid alkyl ester as a monomer unit, has a balance of performance such as adhesion and moisture resistance of the resin composition.
  • the content of ethylene units is preferably 30% by mass or more, more preferably 40% by mass or more, based on the entire copolymer, 50% The mass% or more is even more preferable. For the same reason, 95% by mass or less is preferable, and 90% by mass or less is more preferable.
  • ethylene-butene copolymer, propylene-butene copolymer, isobutylene-butene copolymer, etc. are further copolymerized with other olefins other than ethylene, propylene, isobutylene and butene.
  • ethylene-butene copolymer, propylene-butene copolymer, isobutylene-butene copolymer, etc. are further copolymerized with other olefins other than ethylene, propylene, isobutylene and butene.
  • the ratio of the other olefin units is such that the ethylene unit, butene unit and other
  • the total amount of olefin units, the total amount of propylene units, butene units and other olefin units, or the total amount of isobutylene units, butene units and other olefin units is preferably 20% by mass or less, more preferably 10% by mass or less. Preferably, 5% by mass or less is particularly preferable, and 3% by mass or less is most preferable.
  • ethylene- (meth) acrylic acid alkyl ester copolymer In the modified polyolefin resin of the present invention, ethylene- (meth) acrylic acid alkyl ester copolymer, isobutylene- (meth) acrylic acid alkyl ester copolymer, propylene- (meth) acrylic acid alkyl ester copolymer, etc.
  • ethylene- (meth) acrylic acid alkyl ester copolymer isobutylene- (meth) acrylic acid alkyl ester copolymer
  • propylene- (meth) acrylic acid alkyl ester copolymer etc.
  • a copolymer in which other olefins other than ethylene, propylene and isobutylene are further copolymerized is used, in order to take advantage of the characteristics of the ethylene unit, propylene unit, isobutylene unit, etc.
  • the proportion of olefin units is the total amount of ethylene units, (meth) acrylic acid alkyl ester units and other olefin units, propylene units, (meth) acrylic acid alkyl ester units and other olefin units, or isobutylene units ( (Meth) acrylic acid alkyl ester butene unit
  • the total amount of other olefin units preferably 20 wt% or less, more preferably 10 wt% or less, especially preferably 5 mass% or less, and most preferably 3 wt% or less.
  • the modified polyolefin resin in the present invention is one in which a polyolefin resin is modified with a (meth) acrylic acid alkyl ester and an acid anhydride from the viewpoint of imparting excellent physical properties such as adhesion moisture heat resistance and moisture resistance. That is, the modified polyolefin resin in the present invention is a graft modified product in which a graft chain containing a unit derived from (meth) acrylic acid alkyl ester and a unit derived from an acid anhydride is bonded to the main chain of the polyolefin resin.
  • the (meth) acrylic acid alkyl ester here means an acrylic acid alkyl ester or a methacrylic acid alkyl ester, and each may be used alone, or a mixture of an acrylic acid alkyl ester and a methacrylic acid alkyl ester. Also good.
  • the number of carbon atoms of the alkyl group in the (meth) acrylic acid alkyl ester is preferably 1 to 18, more preferably 1 to 14, still more preferably 1 to 12, particularly preferably 1 to 10, and most preferably 1 to 8. .
  • Specific examples of (meth) acrylic acid alkyl esters include methyl acrylate, ethyl acrylate, n-propyl acrylate, i-propyl acrylate, n-butyl acrylate, i-butyl acrylate, and 2-butyl acrylate.
  • 2-ethylhexyl acrylate, n-butyl methacrylate and the like are preferable, and 2-ethylhexyl acrylate is more preferable.
  • One or more (meth) acrylic acid alkyl esters can be used.
  • acid anhydride examples include succinic anhydride, maleic anhydride, glutaric anhydride, and the like. Particularly preferred is succinic anhydride.
  • One or more acid anhydrides can be used.
  • Polyolefin resins modified with (meth) acrylic acid alkyl esters and acid anhydrides include, for example, polyolefin resins, unsaturated compounds having acid anhydride groups and alkyl (meth) acrylates under radical reaction conditions. It can be obtained by graft modification with an ester (see, for example, JP-A Nos. 2002-173514 and 2006-219627).
  • the number average molecular weight of the graft chain (graft polymer) formed from the (meth) acrylic acid alkyl ester and the acid anhydride is preferably 100 or more, more preferably 200 or more, still more preferably 300 or more.
  • a graft chain having an appropriate length tends not to be formed.
  • the average value of the number average molecular weight of the graft chain (graft polymer) is too small, it tends to be difficult to form a crosslinked structure with an epoxy resin, particularly an epoxy-modified polyolefin resin.
  • the upper limit of the average value of the number average molecular weight of the graft chain (graft polymer) is not particularly limited as long as the functions of the resin composition of the present invention such as sealing performance, adhesion heat resistance, moisture resistance, etc. are exhibited. Is 5000 or less, preferably 3000 or less.
  • the graft chain (graft polymer) preferably contains (meth) acrylic acid alkyl ester units in an amount of 20 wt% to 80 wt%, more preferably 30 wt% to 70 wt%, more preferably 40 wt%. More preferably, the content is 60% by weight or less.
  • the number average molecular weight of the graft chain (graft polymer) can be determined by measuring the molecular weight by the viscosity of the graft modified product, chemical structure analysis of the graft modified product, gel permeation chromatography (GPC) method (polystyrene conversion), and the like.
  • GPC gel permeation chromatography
  • the molecular weight of the polymer component formed only from the added (meth) acrylic acid alkyl ester and acid anhydride, which is not bonded to the main chain of the polyolefin resin, is measured by the GPC method or the like. This can be easily obtained.
  • the number average molecular weight by the GPC method is specifically determined by moving LC-9A / RID-6A manufactured by Shimadzu Corporation as a measuring device and Shodex® K-800P / K-804L / K-804L manufactured by Showa Denko KK as a column. Using toluene or the like as a phase, the measurement can be made at a column temperature of 40 ° C. and calculated using a standard polystyrene calibration curve.
  • a component may be used 1 type or may mix and use 2 or more types. That is, two or more types of graft-modified products having different main-framework polyolefin resins and / or graft polymers can be mixed and used.
  • the concentration and number average molecular weight of the acid anhydride group of the component (A) described below are values in the entire mixture of two or more types of graft-modified products.
  • the number average molecular weight of the graft chain (graft polymer) is also the number average molecular weight of the total graft polymer of the mixture.
  • the concentration of the acid anhydride group in the component (A) is preferably 0.05 to 10 mmol / g, and more preferably 0.1 to 5 mmol / g.
  • the concentration of the acid anhydride group is obtained from the value of the acid value defined as the number of mg of potassium hydroxide required to neutralize the acid present in 1 g of resin according to the description of JIS K2501.
  • the number average molecular weight of the component (A) is not particularly limited, but is preferably 500,000 or less from the viewpoint of providing good coatability of the varnish of the resin composition and good compatibility with other components in the resin composition. 300000 or less is more preferable, and 150,000 or less is still more preferable. On the other hand, it is preferably 10,000 or more, more preferably 30000 or more from the viewpoint of preventing repelling during coating of the varnish of the resin composition, expressing moisture resistance of the formed resin composition layer, and improving mechanical strength. Preferably, 50000 or more is more preferable.
  • the number average molecular weight in this invention is measured by the gel permeation chromatography (GPC) method (polystyrene conversion).
  • the number average molecular weight by the GPC method is specifically determined by moving LC-9A / RID-6A manufactured by Shimadzu Corporation as a measuring device and Shodex® K-800P / K-804L / K-804L manufactured by Showa Denko KK as a column. Using toluene or the like as a phase, the measurement can be made at a column temperature of 40 ° C. and calculated using a standard polystyrene calibration curve.
  • the component (A) is preferably low in crystallinity and particularly preferably noncrystalline from the viewpoint of improving workability.
  • non-crystalline means that the component (A) does not have a clear melting point.
  • DSC differential scanning calorimetry
  • (A) component in the resin composition of this invention brings about the favorable coating property and compatibility of the varnish of a resin composition, and favorable wet heat in the resin composition layer formed From the viewpoint of ensuring resistance and handleability (tack suppression), when the nonvolatile content in the resin composition is 100% by mass, it is preferably 45% by mass or less, more preferably 40% by mass or less, and 35% by mass or less. Further preferred. On the other hand, from the viewpoint of improving moisture permeability and improving transparency, when the nonvolatile content in the resin composition is 100% by mass, 5% by mass or more is preferable, 10% by mass or more is more preferable, and 15% by mass. % Or more is more preferable.
  • the resin composition of the present invention contains an epoxy resin (hereinafter also abbreviated as “component (B)”).
  • An epoxy resin forms a crosslinked structure by reaction with the acid anhydride group which (A) component has.
  • the epoxy resin is not particularly limited as long as it has an average of two or more epoxy groups per molecule.
  • bisphenol A type epoxy resin for example, bisphenol A type epoxy resin, biphenyl type epoxy resin, biphenyl aralkyl type epoxy resin, naphthol type epoxy resin, naphthalene type epoxy resin, bisphenol F type epoxy resin, phosphorus-containing epoxy resin, bisphenol S type epoxy resin, aromatic glycidylamine Type epoxy resin (for example, tetraglycidyldiaminodiphenylmethane, triglycidyl-p-aminophenol, diglycidyltoluidine, diglycidylaniline, etc.), alicyclic epoxy resin, aliphatic chain epoxy resin, phenol novolac type epoxy resin, cresol novolac Type epoxy resin, bisphenol A novolac type epoxy resin, epoxy resin containing polyalkylene glycol skeleton, epoxy resin having butadiene structure, bisphenol And diglycidyl etherified products of naphthalenediol, glycidyl etherified products of phenols, digly
  • epoxy resins bisphenol A type epoxy resin, bisphenol F type epoxy resin, phenol novolac type epoxy resin, biphenyl aralkyl type epoxy resin, phenol aralkyl type epoxy resin, aromatic glycidyl amine type epoxy resin, dicyclopentadiene structure
  • An epoxy resin, a polypropylene glycol skeleton-containing epoxy resin, and the like are preferable, and a bisphenol A type epoxy resin and a polypropylene glycol skeleton-containing epoxy resin are particularly preferable.
  • epoxy resins include “828EL” (liquid bisphenol A type epoxy resin) manufactured by Mitsubishi Chemical Corporation, “HP4032”, “HP4032D” (all naphthalene type bifunctional epoxy resins) manufactured by DIC, and “ “HP4700” (naphthalene type tetrafunctional epoxy resin), DIC's "HP7200 series” (dicyclopentadiene type epoxy resin), Toto Kasei's “ESN-475V”, “ESN-185V” (all naphthol type epoxy resins) “PB-3600” (epoxy resin having a butadiene structure) manufactured by Daicel Chemical Industries, Ltd., “NC3000H”, “NC3000L”, “NC3100”, “NC3000”, “NC3000FH-75M” manufactured by Nippon Kayaku Co., Ltd.
  • the epoxy resin may be liquid or solid, and both liquid and solid may be used.
  • “liquid” and “solid” are states of the epoxy resin at room temperature (25 ° C.).
  • the component (B) preferably has an epoxy equivalent of 100 to 1500 g / eq, more preferably 150 to 1000 g / eq, and still more preferably 200 to 800 g / eq.
  • the “epoxy equivalent” is the number of grams (g / eq) of a resin containing 1 gram equivalent of an epoxy group, and is measured according to the method defined in JIS K 7236.
  • an epoxy-modified polyolefin resin that is, a polyolefin resin having an epoxy group is particularly preferable.
  • the epoxy-modified polyolefin resin include a graft-modified product in which a graft polymer containing a unit of an epoxy group-containing unsaturated compound is bonded to the main chain of the polyolefin resin.
  • the graft-modified product can be obtained by graft-modifying a polyolefin resin with an epoxy group-containing unsaturated compound under radical reaction conditions.
  • Examples of the epoxy group-containing unsaturated compound include glycidyl (meth) acrylate, ⁇ -methylglycidyl (meth) acrylate, 4-hydroxybutyl acrylate glycidyl ether, 2-hydroxyethyl acrylate glycidyl ether, and allyl glycidyl ether. Preferably, it is glycidyl methacrylate. These can use 1 type (s) or 2 or more types.
  • Specific examples of the polyolefin-based resin in the graft-modified product include the same as those exemplified as specific examples of the polyolefin-based resin in the component (A).
  • the epoxy-modified polyolefin-based resin one or two or more kinds selected from the above epoxy group-containing unsaturated compounds and one or two or more olefins are radically copolymerized to obtain an epoxy group-containing unsaturated resin. You may make it obtain as a copolymer containing a compound unit and an olefin unit.
  • Specific examples of the olefin include the same examples as the constituent monomer units of the polyolefin resin having the main skeleton in the modified polyolefin resin of the component (A).
  • the concentration of the epoxy group in the epoxy-modified polyolefin resin is preferably 0.05 to 10 mmol / g, more preferably 0.1 to 5 mmol / g.
  • the epoxy group concentration is determined from the epoxy equivalent obtained based on JIS K 7236-1995.
  • the number average molecular weight of the epoxy-modified polyolefin resin is not particularly limited, but from the viewpoint of providing good coatability of the varnish of the resin composition and good compatibility with other components in the resin composition, it is 500,000 or less. Preferably, 300,000 or less is more preferable, and 150,000 or less is still more preferable. On the other hand, it is preferably 10,000 or more, more preferably 30000 or more from the viewpoint of preventing repelling during coating of the varnish of the resin composition, expressing moisture resistance of the formed resin composition layer, and improving mechanical strength. Preferably, 50000 or more is more preferable. In addition, the number average molecular weight here is measured by a gel permeation chromatography (GPC) method (polystyrene conversion).
  • GPC gel permeation chromatography
  • the number average molecular weight by the GPC method is specifically determined by moving LC-9A / RID-6A manufactured by Shimadzu Corporation as a measuring device and Shodex® K-800P / K-804L / K-804L manufactured by Showa Denko KK as a column. Using toluene or the like as a phase, the measurement can be made at a column temperature of 40 ° C. and calculated using a standard polystyrene calibration curve.
  • the epoxy-modified polyolefin-based resin preferably has low crystallinity from the viewpoint of improving processability, and is particularly preferably amorphous.
  • non-crystalline means that the epoxy-modified polyolefin resin does not have a clear melting point, for example, when the melting point is measured by DSC (differential scanning calorimetry) of the epoxy-modified polyolefin resin. A clear peak is not observed.
  • (B) Component may be used alone or in combination of two or more.
  • limiting in particular in content of (B) component in a resin composition From a viewpoint that favorable moisture-permeable resistance can be ensured, when the non volatile matter in a resin composition is 100 mass%, it is 45 mass% or less. Is preferable, 40 mass% or less is more preferable, and 35 mass% or less is still more preferable.
  • the nonvolatile content in the resin composition is 100% by mass, 5% by mass or more is preferable, 10% by mass or more is more preferable, and 15% by mass. The above is more preferable.
  • the amount ratio of the component (A) and the component (B) in the resin composition of the present invention is arbitrarily selected within the range in which the effect of the present invention is exerted, but forms a good cross-linked structure and unreacted activity. From the viewpoint of reducing the content of functional groups and exhibiting performance stably, the ratio of the acid anhydride equivalent (Ea) of the component (A) to the epoxy equivalent (Eb) of the component (B) (Ea / Eb) However, the ratio is preferably 0.7 to 1.45, more preferably 0.8 to 1.25, still more preferably 0.9 to 1.15, and still more preferably 0.95 to 1.06.
  • the “acid anhydride equivalent” is the number of grams (g / eq) of a resin containing 1 gram equivalent of an acid anhydride group.
  • the total content of the component (A) and the component (B) is not particularly limited, but from the viewpoint of adhesiveness, workability, etc., the nonvolatile content in the resin composition is 100% by mass. 80 mass% or less is preferable, 75 mass% or less is more preferable, and 70 mass% or less is still more preferable. On the other hand, from the viewpoint of wet heat resistance, when the nonvolatile content in the resin composition is 100% by mass, 5% by mass or more is preferable, 10% by mass or more is more preferable, and 15% by mass or more is even more preferable.
  • the (C) tackifier resin (hereinafter also abbreviated as “component (C)”) used in the present invention is also called a tackifier and is a resin that is added to a plastic polymer to impart tackiness.
  • the component (C) is not particularly limited, and includes terpene resins, modified terpene resins (hydrogenated terpene resins, terpene phenol copolymer resins, aromatic modified terpene resins, etc.), coumarone resins, indene resins, petroleum resins ( Aliphatic petroleum resins, hydrogenated alicyclic petroleum resins, aromatic petroleum resins, aliphatic aromatic copolymer petroleum resins, alicyclic petroleum resins, dicyclopentadiene petroleum resins and their hydrides) Preferably used.
  • terpene resins modified terpene resins (hydrogenated terpene resins, terpene phenol copolymer resins, aromatic modified terpene resins, etc.), coumarone resins, indene resins, petroleum resins ( Aliphatic petroleum resins, hydrogenated alicyclic petroleum resins, aromatic petroleum resins, aliphatic aromatic copolymer petroleum resins, alicyclic petroleum resins,
  • terpene resin aromatic modified terpene resin, terpene phenol copolymer resin, hydrogenated alicyclic petroleum resin, aromatic petroleum resin, Aliphatic aromatic copolymer petroleum resins, alicyclic petroleum resins are more preferred, alicyclic petroleum resins are more preferred, alicyclic saturated hydrocarbon resins are even more preferred, cyclohexane ring-containing saturated hydrocarbon resins, Dicyclopentadiene-modified hydrocarbon resin is particularly preferred.
  • component (C) examples include terpene resins such as YS resin PX and YS resin PXN (both manufactured by Yasuhara Chemical Co., Ltd.), and aromatic-modified terpene resins such as YS resin TO and TR series (any Are Yasuhara Chemical Co., Ltd.), and hydrogenated terpene resins include Clearon P, Clearon M, Clearon K series (all manufactured by Yasuhara Chemical Co., Ltd.), and terpene phenol copolymer resins are YS Polystar 2000, Polystar U.
  • alicyclic petroleum resins include Escorez 5300 series, 5600 series (all manufactured by ExxonMobil Corp.), etc. Tribe oil tree ENDEX155 (manufactured by Eastman Co., Ltd.) and the like, quintone D100 (manufactured by Nippon Zeon Co., Ltd.) and the like as aliphatic aromatic copolymer petroleum resins, and quintone 1325 and quintone 1345 (both from Nippon Zeon) as alicyclic petroleum resins.
  • Tribe oil tree ENDEX155 manufactured by Eastman Co., Ltd.
  • quintone D100 manufactured by Nippon Zeon Co., Ltd.
  • quintone 1325 and quintone 1345 both from Nippon Zeon
  • Alcon P100, Alcon P125, Alcon P140 (all manufactured by Arakawa Chemical Co., Ltd.) and the like are listed as hydrogenated alicyclic petroleum resins, and TFS13-030 (Arakawa) is a cyclohexane ring-containing saturated hydrocarbon resin. Chemical Co., Ltd.).
  • the softening point of the component (C) is preferably from 50 to 200 ° C., more preferably from 90 to 180 ° C., from the viewpoint that the sheet softens in the resin composition sheet lamination step and has the desired heat resistance. 150 ° C. is more preferable.
  • the softening point is measured by the ring and ball method according to JIS K2207.
  • the content of the component (C) in the resin composition is not particularly limited, but from the viewpoint of maintaining good moisture resistance of the resin composition, when the nonvolatile content in the resin composition is 100% by mass, 80 mass% or less is preferable, 60 mass% or less is more preferable, and 50 mass% or less is still more preferable. On the other hand, from the viewpoint of having sufficient adhesiveness, when the nonvolatile content in the resin composition is 100% by mass, 5% by mass or more is preferable, 10% by mass or more is more preferable, and 15% by mass or more is even more preferable.
  • the resin composition for sealing containing the polyolefin resin which has an acid anhydride group and / or an epoxy group, and tackifying resin, Preferably, it has the polyolefin resin which has an acid anhydride group, and an epoxy group
  • An encapsulating resin composition containing a polyolefin-based resin and a tackifying resin is exemplified.
  • the polyolefin resin having an acid anhydride group is not particularly limited as long as it is a resin having an acid anhydride group by acid anhydride modification, and is modified with the (meth) acrylic acid alkyl ester and acid anhydride of the component (A).
  • polyolefin-based resin May be a polyolefin-based resin, and may contain other functional groups by other modifications. That is, the “polyolefin resin having an acid anhydride group” is characterized in that the (meth) acrylic acid alkyl ester of the component (A) and the acid are other than that the (meth) acrylic acid alkyl ester modification is not essential.
  • polyolefin resin modified with anhydride the polyolefin resin may be a copolymer, and specific examples of the copolymer include, for example, an ethylene-nonconjugated diene copolymer, an ethylene-butene copolymer, and an ethylene-butene-nonconjugated diene copolymer.
  • tackifying resin is synonymous with the tackifying resin of the said (C) component.
  • the functional group concentration of the acid anhydride group and / or epoxy group of the polyolefin resin having an acid anhydride group and / or epoxy group is preferably 0.05 to 10 mmol / g.
  • the content of the propylene-butene copolymer having an acid anhydride group and / or an epoxy group is preferably 35 to 80% by mass per 100% by mass of the total nonvolatile content in the resin composition.
  • the sealing resin composition here can preferably be used for sealing organic EL elements.
  • the resin composition for sealing materials here is in the form of a sealing sheet and can be used, for example, for organic EL sealing.
  • the resin composition of the present invention (resin composition containing the above components (A) to (C)) and the resin composition of the above reference examples further contain a curing accelerator from the viewpoint of forming a good crosslinked structure. You may let them. Although it does not specifically limit as a hardening accelerator, An amine hardening accelerator, a guanidine hardening accelerator, an imidazole hardening accelerator, a phosphonium hardening accelerator, etc. are mentioned. You may use a hardening accelerator 1 type or in combination of 2 or more types.
  • the amine curing accelerator is not particularly limited, but includes quaternary ammonium salts such as tetramethylammonium bromide and tetrabutylammonium bromide; DBU (1,8-diazabicyclo [5.4.0] undecene-7), DBN (1,5-diazabicyclo [4.3.0] nonene-5), DBU-phenol salt, DBU-octylate, DBU-p-toluenesulfonate, DBU-formate, DBU-phenol novolac resin salt, etc.
  • quaternary ammonium salts such as tetramethylammonium bromide and tetrabutylammonium bromide
  • DBU 1,8-diazabicyclo [5.4.0] undecene-7
  • DBN 1,5-diazabicyclo [4.3.0] nonene-5
  • DBU-phenol salt DBU-octylate
  • the guanidine curing accelerator is not particularly limited, but dicyandiamide, 1-methylguanidine, 1-ethylguanidine, 1-cyclohexylguanidine, 1-phenylguanidine, 1- (o-tolyl) guanidine, dimethylguanidine, diphenylguanidine , Trimethylguanidine, tetramethylguanidine, pentamethylguanidine, 1,5,7-triazabicyclo [4.4.0] dec-5-ene, 7-methyl-1,5,7-triazabicyclo [4.
  • dec-5-ene 1-methyl biguanide, 1-ethyl biguanide, 1-n-butyl biguanide, 1-n-octadecyl biguanide, 1,1-dimethyl biguanide, 1,1-diethyl biguanide, 1- Cyclohexyl biguanide, 1-allyl biguanide, 1-phenyl biguanide And 1- (o-tolyl) biguanide. You may use these 1 type or in combination of 2 or more types.
  • the imidazole curing accelerator is not particularly limited, but 1H-imidazole, 2-methyl-imidazole, 2-phenyl-4-methylimidazole, 1-cyanoethyl-2-ethyl-4-methyl-imidazole, 2-phenyl- 4,5-bis (hydroxymethyl) -imidazole, 1-benzyl-2-methylimidazole, 1-benzyl-2-phenylimidazole, 2-ethyl-4-methylimidazole, 2-phenyl-imidazole, 2-dodecyl-imidazole 2-heptadecylimidazole, 1,2-dimethyl-imidazole and the like. You may use these 1 type or in combination of 2 or more types.
  • the phosphonium curing accelerator is not particularly limited, but triphenylphosphine, phosphonium borate compound, tetraphenylphosphonium tetraphenylborate, n-butylphosphonium tetraphenylborate, tetrabutylphosphonium decanoate, (4-methylphenyl) Examples include triphenylphosphonium thiocyanate, tetraphenylphosphonium thiocyanate, and butyltriphenylphosphonium thiocyanate. You may use these 1 type or in combination of 2 or more types.
  • the curing accelerator may be used alone or in combination of two or more.
  • limiting in particular in content of the hardening accelerator in a resin composition From a viewpoint of preventing the fall of moisture permeability resistance, when the non volatile matter in a resin composition is 100 mass%, 5 mass% or less is Preferably, 1 mass% or less is more preferable.
  • from the viewpoint of suppressing tackiness when the nonvolatile content in the resin composition is 100% by mass, 0.01% by mass or more is preferable, and 0.05% by mass or more is more preferable.
  • the resin composition of the present invention can further contain a hygroscopic metal oxide in order to further improve the moisture permeability resistance.
  • the “hygroscopic metal oxide” means a metal oxide that has a capability of absorbing moisture and chemically reacts with moisture that has been absorbed to become a hydroxide. Specifically, it is one kind selected from calcium oxide, magnesium oxide, strontium oxide, aluminum oxide, barium oxide and the like, or a mixture or solid solution of two or more kinds. Specific examples of the mixture or solid solution of two or more kinds include calcined dolomite (a mixture containing calcium oxide and magnesium oxide), calcined hydrotalcite (solid solution of calcium oxide and aluminum oxide), and the like. It is done.
  • calcium oxide, magnesium oxide, and calcined hydrotalcite are preferable from the viewpoint of high hygroscopicity, cost, and stability of raw materials, and calcined hydrotalcite is more preferable.
  • the calcined hydrotalcite reduces the amount of OH in the chemical structure by calcining natural hydrotalcite (Mg 6 Al 2 (OH) 16 CO 3 ⁇ 4H 2 O) and synthetic hydrotalcite (hydrotalcite-like compound) Or disappeared.
  • a calcined hydrotalcite having a BET specific surface area of 65 m 2 / g or more is particularly preferable.
  • the calcined hydrotalcite having a BET specific surface area of 65 m 2 / g or more preferably has a BET specific surface area of 80 m 2 / g or more, and more preferably 100 m 2 / g or more. Further, BET specific surface area is preferably from 200m 2 / g, more preferably at most 150m 2 / g.
  • the hygroscopic metal oxide is known as a hygroscopic material in various technical fields, and a commercially available product can be used. Specifically, calcium oxide (“Moystop # 10” manufactured by Sankyo Flour Milling Co., Ltd.), magnesium oxide (“Kyowa Mag MF-150”, “Kyowa Mag MF-30” manufactured by Kyowa Chemical Industry Co., Ltd., “Pure Mag” manufactured by Tateho Chemical Industry Co., Ltd. FNMG ”, etc.), lightly burned magnesium oxide (“ TATEHOMAG # 500 ”,“ TATEHOMAG # 1000 ”, TATEHOMAG # 5000”, etc.
  • a surface treated with a surface treatment agent can be used.
  • the surface treatment agent used for the surface treatment for example, higher fatty acids, alkylsilanes, silane coupling agents and the like can be used, and among these, higher fatty acids and alkylsilanes are preferable.
  • One or more surface treatment agents can be used.
  • higher fatty acid examples include higher fatty acids having 18 or more carbon atoms such as stearic acid, montanic acid, myristic acid, and palmitic acid, among which stearic acid is preferable. You may use these 1 type or in combination of 2 or more types.
  • Alkylsilanes include methyltrimethoxysilane, ethyltrimethoxysilane, hexyltrimethoxysilane, octyltrimethoxysilane, decyltrimethoxysilane, octadecyltrimethoxysilane, dimethyldimethoxysilane, octyltriethoxysilane, n-octadecyldimethyl ( And 3- (trimethoxysilyl) propyl) ammonium chloride. You may use these 1 type or in combination of 2 or more types.
  • silane coupling agent examples include 3-glycidyloxypropyltrimethoxysilane, 3-glycidyloxypropyltriethoxysilane, 3-glycidyloxypropyl (dimethoxy) methylsilane, and 2- (3,4-epoxycyclohexyl) ethyltrimethoxy.
  • Epoxy silane coupling agents such as silane; mercapto silane coupling agents such as 3-mercaptopropyltrimethoxysilane, 3-mercaptopropyltriethoxysilane, 3-mercaptopropylmethyldimethoxysilane and 11-mercaptoundecyltrimethoxysilane ; 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-aminopropyldimethoxymethylsilane, N-phenyl-3-aminopropyltri Amino-based silane cups such as toxisilane, N-methylaminopropyltrimethoxysilane, N- (2-aminoethyl) -3-aminopropyltrimethoxysilane and N- (2-aminoethyl) -3-aminopropyldimethoxymethylsilane Ringing agents; Ureido silane coupling agents such
  • the surface treatment of the hygroscopic metal oxide is performed, for example, by adding and spraying the surface treatment agent and stirring for 5 to 60 minutes while stirring and dispersing the untreated hygroscopic metal oxide at room temperature with a mixer.
  • a mixer a well-known mixer can be used, for example, blenders, such as V blender, a ribbon blender, and a bubble cone blender, mixers, such as a Henschel mixer and a concrete mixer, a ball mill, a cutter mill, etc. are mentioned.
  • the hygroscopic material is pulverized with a ball mill or the like
  • a method of surface treatment by mixing the above-mentioned higher fatty acid, alkylsilanes or silane coupling agent is also possible.
  • the treatment amount of the surface treatment agent varies depending on the type of the hygroscopic metal oxide or the type of the surface treatment agent, but is preferably 1 to 10% by mass with respect to the hygroscopic metal oxide.
  • Hygroscopic metal oxides may be used alone or in combination of two or more.
  • the resin composition of the present invention contains a hygroscopic metal compound
  • its content is not particularly limited, but from the viewpoint of preventing the strength of the cured product from being reduced and becoming brittle, the resin composition 50 mass% or less is preferable with respect to 100 mass% of non volatile matters in it, 40 mass% or less is more preferable, and 30 mass% or less is still more preferable.
  • the content is preferably 1% by mass or more, more preferably 5% by mass or more, more preferably 10% by mass with respect to 100% by mass of the nonvolatile content in the resin composition. % Or more is more preferable.
  • the resin composition of the present invention can improve the flexibility and moldability of the resin composition by further containing a plasticizer.
  • a plasticizer A liquid material is suitably used at room temperature.
  • plasticizers include paraffinic process oil, naphthenic process oil, liquid paraffin, polyethylene wax, polypropylene wax, petroleum jelly and other mineral oils, castor oil, cottonseed oil, rapeseed oil, soybean oil, palm oil, palm oil, olive oil. And other liquid oils such as vegetable oil, liquid polybutene, hydrogenated liquid polybutene, liquid polybutadiene, and hydrogenated liquid polybutadiene.
  • liquid poly ⁇ -olefins are preferable, and liquid polybutadiene is particularly preferable.
  • the liquid poly ⁇ -olefin preferably has a low molecular weight from the viewpoint of adhesiveness, and preferably has a weight average molecular weight in the range of 500 to 5000, more preferably 1000 to 3000.
  • plasticizers may be used alone or in combination of two or more.
  • “liquid” means a state of a plasticizer at room temperature (25 ° C.).
  • the resin composition of the present invention contains a plasticizer, when the nonvolatile content in the resin composition is 100% by mass, from the viewpoint of not having an adverse effect on the organic EL element, within the range of 50% by mass or less. used.
  • the resin composition of the present invention may optionally contain various additives other than the above-described components to the extent that the effects of the present invention are not impaired.
  • additives include silica, barium sulfate, talc, clay, mica powder, aluminum hydroxide, magnesium hydroxide, calcium carbonate, magnesium carbonate, boron nitride, aluminum borate, barium titanate, and strontium titanate.
  • Inorganic fillers such as calcium titanate, magnesium titanate, bismuth titanate, titanium oxide, barium zirconate, calcium zirconate; organic fillers such as rubber particles, silicone powder, nylon powder, fluororesin powder; Orben, Benton Thickeners such as silicon-based, fluorine-based, polymer-based antifoaming agents or leveling agents; adhesion imparting agents such as triazole compounds, thiazole compounds, triazine compounds, porphyrin compounds; and the like.
  • the method for preparing the resin composition of the present invention is not particularly limited, and examples thereof include a method in which the compounding ingredients are mixed with a kneading roller, a rotary mixer, or the like, if necessary, by adding a solvent or the like.
  • the resin composition of the present invention is used for sealing electronic parts such as semiconductors, solar cells, high-brightness LEDs, LCDs and EL elements.
  • it is preferably used for sealing an organic EL element, and specifically, applied to the upper part and / or the periphery (side part) of the light emitting part of the organic EL element to protect the light emitting part of the organic EL element from the outside. Can be used.
  • the transparency of the sealing layer formed of the resin composition can be measured with a spectrophotometer.
  • the parallel line transmittance at 450 nm is preferably 80% or more, more preferably 82% or more, still more preferably 84% or more, and still more preferably 86% or more, 88% or more is particularly preferable, and 90% or more is particularly preferable.
  • the resin composition of the present invention comprises (A) an ester bond formed by reacting an acid anhydride group of a polyolefin resin modified with (meth) acrylic acid alkyl ester and an acid anhydride and an epoxy group of (B) an epoxy resin. Is preferably formed.
  • a sealing layer excellent in adhesion moisture heat resistance, moisture permeability resistance, and the like can be formed.
  • an organic solvent is contained in the resin composition, a varnish-like resin composition is prepared, and the varnish is heated and dried. The organic solvent can be dried by blowing hot air or the like.
  • organic solvents examples include ketones such as acetone, methyl ethyl ketone (hereinafter also abbreviated as “MEK”), cyclohexanone; and acetates such as ethyl acetate, butyl acetate, cellosolve acetate, propylene glycol monomethyl ether acetate, and carbitol acetate.
  • ketones such as acetone, methyl ethyl ketone (hereinafter also abbreviated as “MEK”), cyclohexanone
  • acetates such as ethyl acetate, butyl acetate, cellosolve acetate, propylene glycol monomethyl ether acetate, and carbitol acetate.
  • Carbitols such as cellosolve and butyl carbitol
  • aromatic hydrocarbons such as toluene and xylene
  • dimethylformamide dimethylacetamide, N-methylpyrrolidone
  • aromatic mixed solvents examples include “Swazole” (trade name, manufactured by Maruzen Petroleum Corporation) and “Ipsol” (trade name, manufactured by Idemitsu Kosan Co., Ltd.). You may use an organic solvent 1 type or in combination of 2 or more types.
  • Drying conditions are not particularly limited, but preferably 50 to 100 ° C. for 1 to 60 minutes. By setting it as 50 degreeC or more, it becomes easy to reduce the amount of solvent which remains in a resin composition layer.
  • the sealing sheet of the present invention is a sealing sheet in which an adhesive layer is formed on a support, and the adhesive layer is formed of the resin composition of the present invention.
  • the adhesive layer is formed, for example, by preparing a varnish obtained by dissolving the resin composition of the present invention in an organic solvent, and applying and drying the varnish on a support.
  • the organic solvent can be dried by blowing hot air or the like. During this drying, an ester bond formed by the reaction of the acid anhydride group of the component (A) and the epoxy group of the component (B) in the resin composition is formed. It is preferable.
  • the resin composition becomes a pressure-sensitive adhesive resin composition excellent in adhesion moisture heat resistance, moisture permeation resistance, and the like.
  • the organic solvent include those similar to the organic solvent, and the drying conditions can be the same as the drying conditions.
  • the thickness of the adhesive layer in the sealing sheet is preferably 3 ⁇ m to 200 ⁇ m, more preferably 5 ⁇ m to 100 ⁇ m, and even more preferably 5 ⁇ m to 50 ⁇ m.
  • the final sealing structure of interest is a structure in which a sealing substrate is laminated on an adhesive layer (resin composition layer)
  • the portion where moisture can enter is on the side of the adhesive layer. Therefore, by reducing the thickness of the adhesive layer, the area in contact with the outside air on the side portion is reduced. Therefore, it is desirable to reduce the thickness of the adhesive layer in order to block moisture.
  • the layer thickness of the adhesive layer is too small, the element may be damaged when the sealing substrate is bonded, and the workability when the sealing substrate is bonded tends to be lowered.
  • setting the thickness of the adhesive layer within the above preferable range means that the uniformity of the thickness of the adhesive layer after the adhesive layer is transferred to a sealing target (for example, a substrate on which an element such as an organic EL element is formed). It is also effective in maintaining.
  • a support having moisture resistance is preferable.
  • the moisture-proof support include a moisture-proof plastic film, a metal foil such as a copper foil and an aluminum foil, and the like.
  • the plastic film having moisture resistance include a plastic film in which an inorganic substance such as silicon oxide (silica), silicon nitride, SiCN, amorphous silicon or the like is deposited on the surface.
  • examples of the plastic film on which an inorganic substance is deposited on the surface include, for example, polyolefin (for example, polyethylene, polypropylene, polyvinyl chloride, etc.), polyester (for example, polyethylene terephthalate (hereinafter sometimes abbreviated as “PET”). , Polyethylene naphthalate, etc.), plastic films such as polycarbonate and polyimide are preferred, and PET films are particularly preferred.
  • examples of commercially available moisture-proof plastic films include the Tech Barrier HX, AX, LX, L series (Mitsubishi Resin Co., Ltd.) and the moisture barrier effect even more than the Tech Barrier HX, AX, LX, L series. X-BARRIER (manufactured by Mitsubishi Plastics), etc.
  • the support having moisture resistance a support having a multilayer structure of two or more layers, for example, a laminate of the above plastic film and the above metal foil with an adhesive may be used. This is inexpensive and advantageous from the viewpoint of handling properties.
  • the support body which does not have moisture resistance (For example, the single body of the plastic film in which the inorganic substance is not vapor-deposited on the said surface) can also be used for the support body of a resin composition sheet.
  • the thickness of the support is not particularly limited, but is preferably from 10 to 150 ⁇ m, more preferably from 20 to 100 ⁇ m, from the viewpoint of the handleability of the sealing sheet.
  • the surface of the adhesive layer of the present invention has a surface to prevent dust from adhering to the surface of the adhesive layer (resin composition layer) and scratches until it is actually used for forming a sealing structure.
  • the protective film is preferably protected, and as the protective film, the plastic film exemplified in the above support can be used.
  • the protective film may be subjected to a mold release treatment in addition to a mat treatment and a corona treatment.
  • Specific examples of the release agent include a fluorine-based release agent, a silicone-based release agent, and an alkyd resin-based release agent. Different types of release agents may be mixed and used.
  • the thickness of the protective film is not particularly limited, but is preferably 1 to 40 ⁇ m, and more preferably 10 to 30 ⁇ m.
  • the sealing sheet of the present invention is used by being laminated on a sealing target.
  • laminate refers to an adhesive layer (resin composition layer) in which the object to be sealed is covered with a sealing sheet with a support, and the object to be sealed is transferred from the sheet for sealing. ) Covered.
  • a sealing sheet that is a support that does not have moisture resistance for example, a single plastic film with no inorganic material deposited on the surface
  • the sealing sheet is laminated to the object to be sealed. After that, it is preferable to peel the support (that is, transfer the adhesive layer (resin composition layer)), and then separately laminate a sealing substrate on the adhesive layer.
  • the sealing target is a substrate on which an organic EL element is formed (hereinafter, also referred to as “organic EL element forming substrate”)
  • organic EL element forming substrate a mode in which such sealing substrates are laminated.
  • the “sealing substrate” as used in the present invention is the one that uses the moisture-proof support used for the sealing sheet alone without forming an adhesive layer (resin composition layer) on it. It is.
  • a “sealing substrate” also includes a highly moisture-proof plate that does not have flexibility such as a glass plate, a metal plate, and a steel plate, which is unsuitable for use as a support for a sealing sheet.
  • the organic EL device of the present invention is an organic EL device in which an organic EL element is sealed with a sealing layer, and the sealing layer is formed of the resin composition of the present application.
  • the organic EL device of the present invention can be obtained by laminating the sealing sheet of the present invention on a substrate having an organic EL element. When the sealing sheet is protected by a protective film, the organic EL element is removed from the sealing sheet so that the adhesive layer (resin composition layer) is in direct contact with the substrate having the organic EL element. Is laminated on a substrate having The laminating method may be a batch method or a continuous method using a roll.
  • thermosetting is performed. By carrying out like this, the organic EL device by which the organic EL element was sealed with the sealing layer formed with the resin composition of this invention is obtained.
  • a sealing material for an organic EL element needs to be dried before sealing work to remove the absorbed water, and the work is complicated, but the support has moisture resistance. Since the sealing sheet of the present invention using a high moisture permeation resistance, the water absorption rate during storage and device manufacturing operations is also low. Moreover, the damage given to the organic EL element at the time of sealing work is also remarkably reduced.
  • the support sheet When a sealing sheet using a support that does not have moisture resistance is used, the support sheet is peeled off after laminating the sealing sheet on a substrate having an organic EL element, and an exposed adhesive layer (resin composition layer) The sealing process of the organic EL element is completed by pressure-bonding the sealing substrate to the substrate.
  • Two or more sealing substrates may be used by bonding them from the viewpoint of improving the moisture-proof effect.
  • the thickness of the sealing substrate is preferably 5 mm or less, more preferably 1 mm or less, and further preferably 100 ⁇ m or less from the viewpoint of making the organic EL device itself thin and light.
  • the pressure at the time of press-bonding the sealing substrate is preferably about 0.3 to 10 kgf / cm 2 , and 25 to 130 ° C. is preferable when the pressure is applied under heating.
  • the substrate having an organic EL element is an organic EL element formed on a transparent substrate
  • the transparent substrate side is a display surface of a display or a light emitting surface of a lighting fixture
  • a metal plate, metal foil, opaque plastic film, or plate may be used.
  • the sealing substrate side is used as the display surface of the display or the light emitting surface of the lighting fixture. Therefore, a transparent plastic film, a glass plate, a transparent plastic plate or the like is used as the sealing substrate.
  • T-YP429 Modified polyolefin-based resin
  • the maleic anhydride group concentration 0.46 mmol / g, the number average molecular weight 2300 of the modified copolymer, the number average molecular weight 386 of the graft chain, the content of 2-ethylhexyl acrylate units in the graft chain of 50% by mass
  • T-YP430 manufactured by Seiko PMC
  • 2-ethylhexyl acrylate and maleic anhydride modified ethylene-methyl methacrylate copolymer (ethylene unit / methyl methacrylate unit 68% by mass / 32% by mass, maleic an
  • B epoxy resin 828EL (manufactured by Mitsubishi Chemical Corporation) ): Bisphenol A type epoxy resin, epoxy equivalent 190 g / eq EPICLON EXA4850-1000 (manufact
  • the PET film was peeled off, and a glass plate (length 76 mm, width 26 mm, thickness 1.2 mm, micro slide glass) was further laminated on the exposed resin composition layer under the same conditions as described above.
  • pulling speed 50mm / min was measured (initial adhesive strength).
  • adhesive strength was measured by said method (adhesion strength after a high temperature, high humidity environment test).
  • a sealing sheet was obtained by the method described below. Unless otherwise specified, the value of each part is a value converted in terms of nonvolatile content.
  • Example 1 To 37 parts of 2-ethylhexyl acrylate and maleic anhydride modified ethylene-methyl methacrylate copolymer (T-YP429, 20% toluene solution), purified cyclohexane ring-containing saturated hydrocarbon resin (TFS13-030, 60% toluene solution) 35 parts were mixed and mixed with a high-speed rotary mixer to obtain a uniform mixed solution. To this mixed solution, 27 parts of a glycidyl methacrylate-modified ethylene-methacrylate copolymer (T-YP431, 20% toluene solution) and 0.5 part of an anionic polymerization accelerator (TAP) are uniformly mixed with a high-speed rotating mixer.
  • T-YP429 2-ethylhexyl acrylate and maleic anhydride modified ethylene-methyl methacrylate copolymer
  • T-YP431 purified cyclohexane ring-containing saturated hydrocarbon resin
  • the obtained varnish is uniformly coated with a die coater on the release-treated surface of a PET film (thickness 30 ⁇ m) treated with a silicone-based release agent, and is cured by heating at 130 ° C. for 60 minutes.
  • a sealing sheet having a composition layer thickness of 20 ⁇ m was obtained.
  • Example 2 To 37 parts of 2-ethylhexyl acrylate and maleic anhydride modified ethylene-methyl methacrylate copolymer (T-YP430, 20% toluene solution), purified cyclohexane ring-containing saturated hydrocarbon resin (TFS13-030, 60% toluene solution) 35 parts were mixed and mixed with a high-speed rotary mixer to obtain a uniform mixed solution. To this mixed solution, 27 parts of a glycidyl methacrylate-modified ethylene-methyl methacrylate copolymer (T-YP432, 20% toluene solution) and 0.5 part of an anionic polymerization accelerator (TAP) are uniformly mixed with a high-speed rotating mixer.
  • T-YP430 2-ethylhexyl acrylate and maleic anhydride modified ethylene-methyl methacrylate copolymer
  • T-YP432 purified cyclohexane ring-containing saturated hydrocarbon resin
  • the obtained varnish is uniformly coated with a die coater on the release-treated surface of a PET film (thickness 30 ⁇ m) treated with a silicone-based release agent, and is cured by heating at 130 ° C. for 60 minutes.
  • a sealing sheet having a composition layer thickness of 20 ⁇ m was obtained.
  • Example 3 30 parts of 2-ethylhexyl acrylate and maleic anhydride modified ethylene-methyl methacrylate copolymer (T-YP429, 20% swazole solution), purified cyclohexane ring-containing saturated hydrocarbon resin (TFS13-030, 60% toluene solution) 35 parts were mixed and mixed with a high-speed rotary mixer to obtain a uniform mixed solution. To this mixed solution, 34 parts of an ethylene-glycidyl methacrylate copolymer (BONDAST BF-7M, 20% swazole solution) and 0.5 part of an anionic polymerization accelerator (TAP) were uniformly mixed with a high-speed rotary mixer. A varnish was obtained.
  • T-YP429 2-ethylhexyl acrylate and maleic anhydride modified ethylene-methyl methacrylate copolymer
  • T-YP429 purified cyclohexane ring-containing saturated hydrocarbon resin
  • TEP anionic
  • the obtained varnish is uniformly coated with a die coater on the release-treated surface of a PET film (thickness 30 ⁇ m) treated with a silicone-based release agent, and is cured by heating at 130 ° C. for 60 minutes.
  • a sealing sheet having a composition layer thickness of 20 ⁇ m was obtained.
  • Example 4 Mixture of 2-ethylhexyl acrylate and maleic anhydride modified ethylene-propylene copolymer and 2-ethylhexyl acrylate and maleic anhydride modified propylene-butene copolymer (T-YP953, 30% methylcyclohexane + butyl acetate solution) 37 36 parts of a cyclohexane ring-containing saturated hydrocarbon resin purified product (TFS13-030, 60% toluene solution) was mixed with a high-speed rotary mixer to obtain a uniform mixed solution.
  • T-YP953, 30% methylcyclohexane + butyl acetate solution 37 36 parts of a cyclohexane ring-containing saturated hydrocarbon resin purified product (TFS13-030, 60% toluene solution) was mixed with a high-speed rotary mixer to obtain a uniform mixed solution.
  • Example 5 Mixture of 2-ethylhexyl acrylate and maleic anhydride modified ethylene-propylene copolymer and 2-ethylhexyl acrylate and maleic anhydride modified propylene-butene copolymer (T-YP955, 30% methylcyclohexane + butyl acetate solution) 25 36 parts of a cyclohexane ring-containing saturated hydrocarbon resin purified product (TFS13-030, 60% toluene solution) was mixed with a high-speed rotary mixer to obtain a uniform mixed solution.
  • T-YP955 30% methylcyclohexane + butyl acetate solution
  • Example 6 To 16 parts of 2-ethylhexyl acrylate and maleic anhydride modified ethylene-propylene-butene random copolymer (T-YP956, 50% methylcyclohexane + butyl acetate solution) purified cyclohexane ring-containing saturated hydrocarbon resin (TFS13-030) , 60% toluene solution) was mixed and mixed with a high-speed rotary mixer to obtain a uniform mixed solution.
  • T-YP956 50% methylcyclohexane + butyl acetate solution
  • T-YP956 50% methylcyclohexane + butyl acetate solution
  • Example 7 50 parts of 2-ethylhexyl acrylate and maleic anhydride-modified propylene-butene copolymer (T-YP279, 40% swazole solution) and 50% purified cyclohexane ring-containing saturated hydrocarbon resin (TFS13-030, 60% toluene solution) The parts were mixed and mixed with a high-speed rotary mixer to obtain a uniform mixed solution.
  • Example 8 50 parts of cyclohexane ring-containing saturated hydrocarbon resin (TFS13-030, 60% toluene solution) is added to 35 parts of 2-ethylhexyl acrylate and maleic anhydride modified propylene-butene copolymer (T-YP279, 40% swazole solution). The parts were mixed and mixed with a high-speed rotary mixer to obtain a uniform mixed solution. To this mixed solution, 2 parts of bisphenol A type epoxy resin (828EL) and 0.5 part of an anionic polymerization accelerator (TAP) were uniformly mixed with a high-speed rotary mixer to obtain a varnish.
  • T-YP279 2-ethylhexyl acrylate and maleic anhydride modified propylene-butene copolymer
  • the obtained varnish is uniformly coated with a die coater on the release-treated surface of a PET film (thickness 30 ⁇ m) treated with a silicone-based release agent, and is cured by heating at 130 ° C. for 60 minutes.
  • a sealing sheet having a composition layer thickness of 20 ⁇ m was obtained.
  • Example 9 50 parts of cyclohexane ring-containing saturated hydrocarbon resin (TFS13-030, 60% toluene solution) is added to 35 parts of 2-ethylhexyl acrylate and maleic anhydride modified propylene-butene copolymer (T-YP279, 40% swazole solution). The parts were mixed and mixed with a high-speed rotary mixer to obtain a uniform mixed solution. To this mixed solution, 2 parts of an epoxy resin containing polypropylene glycol skeleton (EPICLON EXA4850-1000) and 0.5 part of an anionic polymerization accelerator (TAP) were uniformly mixed with a high-speed rotary mixer to obtain a varnish.
  • T-YP279 2-ethylhexyl acrylate and maleic anhydride modified propylene-butene copolymer
  • the obtained varnish is uniformly coated with a die coater on the release-treated surface of a PET film (thickness 30 ⁇ m) treated with a silicone-based release agent, and is cured by heating at 130 ° C. for 60 minutes.
  • a sealing sheet having a composition layer thickness of 20 ⁇ m was obtained.
  • Example 10 20 parts of 2-ethylhexyl acrylate and maleic anhydride modified propylene-butene copolymer (T-YP279, 40% swazole solution) and 14 parts of calcined hydrotalcite were mixed and kneaded with three rolls, and then cyclohexane ring-containing saturated 50 parts of purified hydrocarbon resin (TFS13-030, 60% toluene solution) was mixed with a high-speed rotary mixer to obtain a uniform mixed solution.
  • T-YP279 2-ethylhexyl acrylate and maleic anhydride modified propylene-butene copolymer
  • 14 parts of calcined hydrotalcite 14 parts of calcined hydrotalcite was mixed and kneaded with three rolls, and then cyclohexane ring-containing saturated 50 parts of purified hydrocarbon resin (TFS13-030, 60% toluene solution) was mixed with a high-speed rotary mixer to obtain a
  • Example 11 28 parts of 2-ethylhexyl acrylate and maleic anhydride modified propylene-butene copolymer (T-YP312, 40% swazole solution) and purified hydrocarbon resin containing cyclohexane ring (TFS13-030, 60% toluene solution) 50 parts were mixed and mixed with a high-speed rotary mixer to obtain a uniform mixed solution. To this mixed solution, 21 parts of a glycidyl methacrylate-modified propylene-butene copolymer (T-YP313, 40% swazole solution) and 0.5 part of an anionic polymerization accelerator (TAP) were uniformly mixed with a high-speed rotary mixer.
  • T-YP312 2-ethylhexyl acrylate and maleic anhydride modified propylene-butene copolymer
  • T-YP313 purified hydrocarbon resin containing cyclohexane ring
  • TEP anionic polymer
  • the obtained varnish is uniformly coated with a die coater on the release-treated surface of a PET film (thickness 30 ⁇ m) treated with a silicone-based release agent, and is cured by heating at 130 ° C. for 60 minutes.
  • a sealing sheet having a composition layer thickness of 20 ⁇ m was obtained.
  • ⁇ Comparative Example 1> Mix 50 parts polypropylene resin (L-MODU S400, 45% swazole solution) and 50 parts purified cyclohexane ring-containing saturated hydrocarbon resin (TFS13-030, 60% toluene solution), and mix evenly with a high-speed rotary mixer. A solution was obtained. To this mixed solution, 0.5 part of an anionic polymerization accelerator (TAP) was uniformly mixed with a high-speed rotary mixer to obtain a varnish. The obtained varnish is uniformly coated with a die coater on the release-treated surface of a PET film (thickness 30 ⁇ m) treated with a silicone-based release agent, and is cured by heating at 130 ° C. for 60 minutes. A sealing sheet having a composition layer thickness of 20 ⁇ m was obtained.
  • TEP anionic polymerization accelerator
  • ⁇ Comparative example 2> Mix 50 parts of styrene-isobutylene-styrene block copolymer (SIBSTAR-102T, 45% swazole solution) and 50 parts of purified cyclohexane ring-containing saturated hydrocarbon resin (TFS13-030, 60% toluene solution). To obtain a homogeneous mixed solution. To this mixed solution, 0.5 part of an anionic polymerization accelerator (TAP) was uniformly mixed with a high-speed rotary mixer to obtain a varnish.
  • SIBSTAR-102T 45% swazole solution
  • TEP anionic polymerization accelerator
  • the obtained varnish is uniformly coated with a die coater on the release-treated surface of a PET film (thickness 30 ⁇ m) treated with a silicone-based release agent, and is cured by heating at 130 ° C. for 60 minutes.
  • a resin composition sheet having a composition layer thickness of 20 ⁇ m was obtained.
  • TAP anionic polymerization accelerator
  • Table 1 shows the evaluation results of Examples and Comparative Examples.
  • the encapsulating resin composition of the present invention has good adhesive moist heat resistance and moisture permeability resistance. Also, the processability was good and stable coating was possible.
  • the resin composition of the present invention has both good adhesiveness and adhesive wet heat resistance, and is suitably used for sealing electronic parts such as semiconductors, solar cells, high-brightness LEDs, LCDs, EL elements, etc., and particularly organic EL elements. It is suitably used for sealing.

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WO2019159830A1 (ja) * 2018-02-16 2019-08-22 三井化学株式会社 画像表示装置封止材および画像表示装置封止シート
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US20220029133A1 (en) * 2018-12-07 2022-01-27 Lg Chem, Ltd Encapsulation composition
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DE112021005948T5 (de) 2020-11-13 2023-09-21 Ajinomoto Co., Inc. Dichtungsbahn

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