WO2016136715A1 - Agent d'encapsulation pour élément d'affichage électroluminescent organique - Google Patents

Agent d'encapsulation pour élément d'affichage électroluminescent organique Download PDF

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Publication number
WO2016136715A1
WO2016136715A1 PCT/JP2016/055191 JP2016055191W WO2016136715A1 WO 2016136715 A1 WO2016136715 A1 WO 2016136715A1 JP 2016055191 W JP2016055191 W JP 2016055191W WO 2016136715 A1 WO2016136715 A1 WO 2016136715A1
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meth
organic
weight
acrylate
sealing agent
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PCT/JP2016/055191
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English (en)
Japanese (ja)
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康雄 渡邊
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積水化学工業株式会社
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Priority to JP2016511838A priority Critical patent/JP6062107B1/ja
Priority to CN201680002382.9A priority patent/CN106797685B/zh
Priority to KR1020177001478A priority patent/KR102641589B1/ko
Publication of WO2016136715A1 publication Critical patent/WO2016136715A1/fr

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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
    • H10K59/80—Constructional details
    • H10K59/87—Passivation; Containers; Encapsulations
    • H10K59/871—Self-supporting sealing arrangements
    • H10K59/8722—Peripheral sealing arrangements, e.g. adhesives, sealants
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/20—Oxides; Hydroxides
    • C08K3/22—Oxides; Hydroxides of metals
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L51/00—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
    • C08L51/04—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers grafted on to rubbers
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/20—Oxides; Hydroxides
    • C08K3/22—Oxides; Hydroxides of metals
    • C08K2003/2206—Oxides; Hydroxides of metals of calcium, strontium or barium
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/20—Oxides; Hydroxides
    • C08K3/22—Oxides; Hydroxides of metals
    • C08K2003/2217—Oxides; Hydroxides of metals of magnesium
    • C08K2003/2224—Magnesium hydroxide
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K2201/00—Specific properties of additives
    • C08K2201/002—Physical properties
    • C08K2201/006—Additives being defined by their surface area
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2207/00—Properties characterising the ingredient of the composition
    • C08L2207/53—Core-shell polymer
    • 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
    • C09K2200/00—Chemical nature of materials in mouldable or extrudable form for sealing or packing joints or covers
    • C09K2200/02—Inorganic compounds
    • C09K2200/0239—Oxides, hydroxides, carbonates
    • 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
    • C09K2200/00—Chemical nature of materials in mouldable or extrudable form for sealing or packing joints or covers
    • C09K2200/06—Macromolecular organic compounds, e.g. prepolymers
    • C09K2200/0607—Rubber or rubber derivatives

Definitions

  • the present invention relates to a sealing agent for organic electroluminescence display elements that is excellent in barrier properties and toughness of a cured product.
  • organic electroluminescence (hereinafter, also referred to as “organic EL”) display element has a laminated structure in which an organic light emitting material layer is sandwiched between a pair of electrodes facing each other, and the organic light emitting material layer is formed from one electrode on the organic light emitting material layer.
  • organic EL organic electroluminescence
  • the organic EL display element performs self-emission, it has better visibility than a liquid crystal display element that requires a backlight, can be reduced in thickness, and can be driven by a DC low voltage. Has the advantage.
  • the organic light-emitting material layer and electrodes constituting the organic EL display element have a problem that the characteristics are easily deteriorated by moisture, oxygen, and the like. Therefore, in order to obtain a practical organic EL display element, it is necessary to extend the life by blocking the organic light emitting material layer and the electrode from the atmosphere.
  • a sealant for example, Patent Document 1.
  • an inorganic film called a passivation film is usually provided on a laminate having an organic light emitting material layer in order to sufficiently suppress the transmission of moisture, oxygen, and the like. A method of sealing the top with a sealant is used.
  • a top emission type organic element that extracts light from the upper surface side of the organic light emitting layer is used.
  • EL display elements have attracted attention. This method has an advantage that it has a high aperture ratio and is driven at a low voltage, which is advantageous for extending the life.
  • a transparent moisture-proof substrate such as glass is interposed on the upper surface side of the light emitting element via a transparent sealing resin.
  • An object of this invention is to provide the sealing agent for organic electroluminescent display elements which is excellent in the barrier property and toughness of hardened
  • the present invention comprises a cationically polymerizable compound, olefinic rubber particles, a photocationic polymerization initiator, an alkaline earth metal-based and / or magnesium-based water-absorbing filler, and the olefinic rubber particles are core-shell It is the sealing agent for organic electroluminescent display elements which has a structure.
  • the present invention is described in detail below.
  • the present inventor has found that alkaline earth metal type such as calcium oxide and / or magnesium type It has been found that particularly excellent barrier properties are exhibited when a water-absorbing filler is used. However, when such a water-absorbing filler is used, a cured product of the obtained sealing agent for organic EL display elements expands in a reliability test under a high-temperature and high-humidity condition, etc. When a substrate is used, there is a problem that cracks occur due to bending.
  • the present inventor used a combination of a cationic polymerizable compound and an olefin rubber particle having a core-shell structure as a resin component, and dispersed the alkaline earth metal-based and / or magnesium-based water-absorbing filler. As a result, it was found that an encapsulant for organic EL display elements excellent in both barrier properties and toughness of the cured product can be obtained, and the present invention has been completed.
  • the sealing agent for organic EL display elements of this invention contains a cationically polymerizable compound.
  • the cationic polymerizable compound include compounds having an epoxy group, an oxetanyl group, a vinyl ether group, and the like as the cationic polymerizable group.
  • a compound having an epoxy group is preferable.
  • an epoxy resin having a bisphenol skeleton, an epoxy resin having a novolak skeleton, an epoxy resin having a naphthalene skeleton, and at least one epoxy resin selected from the group consisting of epoxy resins having a dicyclopentadiene skeleton are preferable,
  • An epoxy resin having a bisphenol skeleton is more preferable, and a bisphenol A type epoxy resin and a bisphenol F type epoxy resin are still more preferable.
  • R 1 to R 18 are a hydrogen atom, a halogen atom, or a hydrocarbon group that may contain an oxygen atom or a halogen atom, and may be the same or different. Also good.
  • X is a bond, an oxygen atom, an alkylene group having 1 to 5 carbon atoms, an oxycarbonyl group, an alkyleneoxycarbonyl group having 2 to 5 carbon atoms, or a secondary amino group.
  • R 19 to R 21 are linear or branched alkylene groups having 2 to 10 carbon atoms, which may be the same or different.
  • E 1 to E 3 each independently represents an organic group represented by the following formula (3-1) or the following formula (3-2).
  • R 22 represents a hydrogen atom or a methyl group.
  • Examples of commercially available cationic polymerizable compounds include EPICLON EXA-830LVP (manufactured by DIC), jER 4005P (manufactured by Mitsubishi Chemical), Celoxide 8000, Celoxide 2021P (all manufactured by Daicel), and TEPIC. -VL (manufactured by Nissan Chemical Co., Ltd.)
  • the sealing agent for organic EL display elements of the present invention contains olefin rubber particles.
  • the olefin rubber particles have a core-shell structure.
  • the obtained cured product of the sealing agent for organic EL display elements is excellent in toughness.
  • the olefin rubber particles have a lower decomposability than other rubber particles, they also have an effect of suppressing the generation of outgas.
  • the olefin-based rubber particle includes a core layer made of a conjugated diene rubber and a resin having a segment derived from a compound having a polymerizable unsaturated double bond. It is preferable to have a shell layer.
  • conjugated diene rubber examples include butadiene rubber, styrene / butadiene rubber, isoprene rubber, chloroprene rubber, and the like. Of these, butadiene rubber is preferable.
  • the conjugated diene rubber preferably has a glass transition temperature (Tg) of 0 ° C. or lower.
  • Examples of the compound having a polymerizable unsaturated double bond include (meth) acrylic compounds, styrene compounds, acrylonitrile compounds, and the like. Of these, (meth) acrylic compounds are preferred. In the present specification, the “(meth) acryl” means acryl or methacryl.
  • Examples of the monofunctional compounds among the (meth) acrylic compounds include, for example, methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, t -Butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, isooctyl (meth) acrylate, n-octyl (meth) acrylate, isononyl (meth) acrylate, isodecyl (meth) acrylate, lauryl (meth) acrylate, isomyristyl ( (Meth) acrylate, stearyl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, bicyclopentenyl (meth) acrylate, benzy
  • Examples of the bifunctional compounds among the (meth) acrylic compounds include 1,3-butanediol di (meth) acrylate, 1,4-butanediol di (meth) acrylate, and 1,6-hexanediol di (meth) acrylate.
  • those having three or more functions include, for example, pentaerythritol tri (meth) acrylate, trimethylolpropane tri (meth) acrylate, propylene oxide-added trimethylolpropane tri (meth) acrylate, ethylene oxide-added tri Methylolpropane tri (meth) acrylate, caprolactone-modified trimethylolpropane tri (meth) acrylate, ethylene oxide-added isocyanuric acid tri (meth) acrylate, glycerin tri (meth) acrylate, propylene oxide-added glycerin tri (meth) acrylate, tris (meth) Acryloyloxyethyl phosphate, pentaerythritol tetra (meth) acrylate, ditrimethylolpropane tetra (meth) acrylate , Dipentaerythritol pen
  • styrene compound examples include styrene, ⁇ -methylstyrene, divinylbenzene, and the like.
  • acrylonitrile-based compound examples include acrylonitrile and methacrylonitrile.
  • the olefin-based rubber particle may be a two-layer structure including the core layer and the shell layer as long as it has the core-shell structure, and further intermediate between the core layer and the shell layer. It may be a multilayer structure having three or more layers.
  • the olefin rubber particles have a preferable lower limit of the average particle diameter of 10 nm and a preferable upper limit of 2000 nm.
  • the average particle diameter of the olefin rubber particles is 10 nm or more, the obtained cured product of the sealing agent for organic EL display elements is excellent in toughness.
  • the average particle diameter of the olefin-based rubber particles is 2000 nm or less, the coverage of the shell layer is increased, and the transparency when used as a surface material is improved.
  • a more preferable upper limit of the average particle diameter of the olefin rubber particles is 300 nm, and a more preferable upper limit is 100 nm.
  • the average particle diameter of the olefin rubber particles can be measured using, for example, a laser diffraction particle size distribution measuring device.
  • a laser diffraction particle size distribution measuring device Mastersizer 2000 (manufactured by Malvern) or the like can be used.
  • the content of the olefinic rubber particles is preferably 5.0 parts by weight with respect to 100 parts by weight of the cationic polymerizable compound, and 80 parts by weight with respect to the preferred upper limit.
  • the content of the olefinic rubber particles is 5.0 parts by weight or more, the cured product of the obtained sealing agent for organic EL display elements is more excellent in toughness.
  • the content of the olefinic rubber particles is 80 parts by weight or less, the cured product of the obtained sealing agent for organic EL display elements is more excellent in barrier properties.
  • the minimum with more preferable content of the said olefin type rubber particle is 10 weight part, and a more preferable upper limit is 70 weight part.
  • the sealing agent for organic EL display elements of this invention contains a photocationic polymerization initiator.
  • the photocationic polymerization initiator is not particularly limited as long as it generates a protonic acid or a Lewis acid by light irradiation, and may be an ionic photoacid generating type or a nonionic photoacid generating type. May be.
  • Examples of the ionic photoacid-generating photocationic polymerization initiator include an anion moiety of BF 4 ⁇ , PF 6 ⁇ , SbF 6 ⁇ , or (BX 4 ) ⁇ (wherein X is at least two or more.
  • aromatic sulfonium salt examples include bis (4- (diphenylsulfonio) phenyl) sulfide bishexafluorophosphate, bis (4- (diphenylsulfonio) phenyl) sulfide bishexafluoroantimonate, and bis (4- ( Diphenylsulfonio) phenyl) sulfide bistetrafluoroborate, bis (4- (diphenylsulfonio) phenyl) sulfide tetrakis (pentafluorophenyl) borate, diphenyl-4- (phenylthio) phenylsulfonium hexafluorophosphate, diphenyl-4- ( Phenylthio) phenylsulfonium hexafluoroantimonate, diphenyl-4- (phenylthio) phenylsulfonium tetraflu
  • aromatic iodonium salt examples include diphenyliodonium hexafluorophosphate, diphenyliodonium hexafluoroantimonate, diphenyliodonium tetrafluoroborate, diphenyliodonium tetrakis (pentafluorophenyl) borate, bis (dodecylphenyl) iodonium hexafluorophosphate, bis (Dodecylphenyl) iodonium hexafluoroantimonate, bis (dodecylphenyl) iodonium tetrafluoroborate, bis (dodecylphenyl) iodonium tetrakis (pentafluorophenyl) borate, 4-methylphenyl-4- (1-methylethyl) phenyliodonium hexa Fluorophosphate, 4-methylphenyl-4- (1-methylethy
  • aromatic diazonium salt examples include phenyldiazonium hexafluorophosphate, phenyldiazonium hexafluoroantimonate, phenyldiazonium tetrafluoroborate, and phenyldiazonium tetrakis (pentafluorophenyl) borate.
  • aromatic ammonium salt examples include 1-benzyl-2-cyanopyridinium hexafluorophosphate, 1-benzyl-2-cyanopyridinium hexafluoroantimonate, 1-benzyl-2-cyanopyridinium tetrafluoroborate, 1-benzyl -2-Cyanopyridinium tetrakis (pentafluorophenyl) borate, 1- (naphthylmethyl) -2-cyanopyridinium hexafluorophosphate, 1- (naphthylmethyl) -2-cyanopyridinium hexafluoroantimonate, 1- (naphthylmethyl)
  • Examples include -2-cyanopyridinium tetrafluoroborate and 1- (naphthylmethyl) -2-cyanopyridinium tetrakis (pentafluorophenyl) borate.
  • Examples of the (2,4-cyclopentadien-1-yl) ((1-methylethyl) benzene) -Fe salt include (2,4-cyclopentadien-1-yl) ((1-methylethyl) benzene.
  • nonionic photoacid-generating photocationic polymerization initiator examples include nitrobenzyl ester, sulfonic acid derivative, phosphoric acid ester, phenolsulfonic acid ester, diazonaphthoquinone, N-hydroxyimide sulfonate, and the like.
  • photocationic polymerization initiators examples include, for example, DTS-200 (manufactured by Midori Chemical Co., Ltd.), UVI6990, UVI6974 (all manufactured by Union Carbide), SP-150, SP-170 (all ADEKA), FC-508, FC-512 (all from 3M), IRGACURE 261 (BASF), PI 2074 (Rhodia) and the like.
  • the content of the cationic photopolymerization initiator is preferably 0.1 parts by weight and preferably 10 parts by weight with respect to 100 parts by weight of the cationic polymerizable compound.
  • the content of the cationic photopolymerization initiator is 0.1 parts by weight or more, the obtained sealing agent for organic EL display elements is more excellent in photocurability.
  • the content of the cationic photopolymerization initiator is 10 parts by weight or less, the curing reaction of the obtained sealing agent for organic EL display elements does not become too fast, and the workability becomes excellent, and the cured product becomes more uniform. Can be.
  • the minimum with more preferable content of the said photocationic polymerization initiator is 0.5 weight part, and a more preferable upper limit is 5 weight part.
  • the sealing agent for organic EL display elements of the present invention contains an alkaline earth metal-based and / or magnesium-based water-absorbing filler.
  • the cured product of the obtained sealing agent for organic EL display elements has excellent barrier properties.
  • Examples of the alkaline earth metal-based and / or magnesium-based water-absorbing filler include calcium oxide, magnesium oxide, barium oxide, and strontium oxide.
  • the alkaline earth metal-based water-absorbing filler and the magnesium-based water-absorbing filler are contained in combination, it is preferable to contain a combination of calcium oxide and magnesium oxide, and a double salt of calcium carbonate and magnesium carbonate. It is more preferable to contain light-burned dolomite obtained by heating dolomite.
  • a preferable lower limit is 3.0 parts by weight and a preferable upper limit is 100 parts by weight with respect to 100 parts by weight of the cationic polymerizable compound.
  • the content of the alkaline earth metal-based and / or magnesium-based water-absorbing filler is 3.0 parts by weight or more, the cured product of the obtained sealing agent for organic EL display elements has better barrier properties. Become. When the content of the alkaline earth metal-based and / or magnesium-based water-absorbing filler is 100 parts by weight or less, the toughness of the cured product of the obtained sealing agent for organic EL display elements is improved, and cracks are generated.
  • the more preferable lower limit of the content of the alkaline earth metal-based and / or magnesium-based water-absorbing filler is 5.0 parts by weight, and the more preferable upper limit is 80 parts by weight.
  • the total surface area of the water-absorptive filler of the alkaline earth metal-based and / or magnesium-based is 10 m 2 per 100g the cationic polymerizable compound, the desirable upper limit is 200 meters 2.
  • the total surface area of the alkaline earth metal-based and / or magnesium-based water-absorbing filler is 10 m 2 or more, the obtained cured product of the sealing agent for organic EL display elements has excellent barrier properties.
  • the total surface area of the alkaline earth metal-based and / or magnesium-based water-absorbing filler is 200 m 2 or less, the toughness of the cured product of the obtained sealing agent for organic EL display elements is improved, and the occurrence of cracks and It will be more excellent in the effect which suppresses panel peeling.
  • the preferable lower limit of the total surface area of the alkaline earth metal-based and / or magnesium-based water-absorbing filler is 20 m 2
  • the preferable upper limit is 150 m 2 .
  • the total surface area of the alkaline earth metal-based and / or magnesium-based water-absorbing filler is calculated from the content of the alkaline-earth metal-based and / or magnesium-based water-absorbing filler and the BET specific surface area. Specifically, for example, it is calculated from the BET specific surface area measured using nitrogen gas with a specific surface area measuring device (manufactured by Shimadzu Corporation, ASAP-2000).
  • the sealing agent for organic EL display elements of the present invention is used for the alkaline earth metal-based and / or magnesium-based water-absorbing fillers within the range not impairing the object of the present invention for the purpose of improving adhesiveness.
  • other fillers may be contained.
  • the other fillers include inorganic fillers such as silica, talc, and alumina, and organic fillers such as polyester fine particles, polyurethane fine particles, vinyl polymer fine particles, and acrylic polymer fine particles. Of these, talc is preferred because of its excellent effect of improving moisture resistance.
  • the content of the other filler is such that a preferred lower limit is 5 parts by weight and a preferred upper limit is 100 parts by weight with respect to 100 parts by weight of the cationic polymerizable compound.
  • a preferred lower limit is 5 parts by weight
  • a preferred upper limit is 100 parts by weight with respect to 100 parts by weight of the cationic polymerizable compound.
  • the minimum with more preferable content of the said other filler is 10 weight part, and a more preferable upper limit is 80 weight part.
  • the sealing agent for organic EL display elements of the present invention may contain a thermosetting agent.
  • thermosetting agent include hydrazide compounds, imidazole derivatives, acid anhydrides, dicyandiamides, guanidine derivatives, modified aliphatic polyamines, addition products of various amines and epoxy resins, and the like.
  • hydrazide compound examples include 1,3-bis (hydrazinocarbonoethyl-5-isopropylhydantoin), sebacic acid dihydrazide, isophthalic acid dihydrazide, adipic acid dihydrazide, malonic acid dihydrazide, and the like.
  • imidazole derivatives examples include 1-cyanoethyl-2-phenylimidazole, N- (2- (2-methyl-1-imidazolyl) ethyl) urea, 2,4-diamino-6- (2′-methylimidazolyl- (1 ′))-ethyl-s-triazine, N, N′-bis (2-methyl-1-imidazolylethyl) urea, N, N ′-(2-methyl-1-imidazolylethyl) -adipamide, 2- Examples include phenyl-4-methyl-5-hydroxymethylimidazole and 2-phenyl-4,5-dihydroxymethylimidazole.
  • acid anhydride examples include tetrahydrophthalic anhydride, ethylene glycol bis (anhydrotrimellitate), and the like. These thermosetting agents may be used independently and 2 or more types may be used together.
  • thermosetting agents examples include SDH (manufactured by Nippon Finechem Co., Ltd.), ADH (manufactured by Otsuka Chemical Co., Ltd.), Amicure VDH, Amicure VDH-J, Amicure UDH (all manufactured by Ajinomoto Fine Techno Co., Ltd.). ) And the like.
  • the content of the thermosetting agent is preferably 0.5 parts by weight and preferably 30 parts by weight with respect to 100 parts by weight of the cationic polymerizable compound.
  • the content of the thermosetting agent is 0.5 parts by weight or more, the obtained sealing agent for organic EL display elements is more excellent in thermosetting.
  • the content of the thermosetting agent is 30 parts by weight or less, the obtained sealing agent for organic EL display elements is excellent in storage stability, and the cured product is excellent in moisture resistance.
  • the minimum with more preferable content of the said thermosetting agent is 1 weight part, and a more preferable upper limit is 15 weight part.
  • the sealing agent for organic EL display elements of the present invention may contain a sensitizer.
  • the sensitizer has a role of further improving the polymerization initiation efficiency of the photocationic polymerization initiator and further promoting the curing reaction of the encapsulant for organic EL display elements of the present invention.
  • the sensitizer examples include anthracene compounds such as 9,10-dibutoxyanthracene, thioxanthone compounds such as 2,4-diethylthioxanthone, 2,2-dimethoxy-1,2-diphenylethane-1, and the like.
  • anthracene compounds such as 9,10-dibutoxyanthracene
  • thioxanthone compounds such as 2,4-diethylthioxanthone, 2,2-dimethoxy-1,2-diphenylethane-1, and the like.
  • -One benzophenone, 2,4-dichlorobenzophenone, methyl o-benzoylbenzoate, 4,4'-bis (dimethylamino) benzophenone, 4-benzoyl-4'methyldiphenyl sulfide, and the like.
  • the content of the sensitizer is preferably 0.05 parts by weight and preferably 3 parts by weight with respect to 100 parts by weight of the cationic polymerizable compound.
  • the sensitizing effect is more exhibited.
  • the content of the sensitizer is 3 parts by weight or less, light can be transmitted to a deep part without excessive absorption.
  • the minimum with more preferable content of the said sensitizer is 0.1 weight part, and a more preferable upper limit is 1 weight part.
  • the sealing agent for organic EL display elements of the present invention preferably contains a stabilizer for the purpose of improving storage stability.
  • the stabilizer include amine compounds and aminophenol type epoxy resins.
  • the content of the stabilizer is preferably 0.001 part by weight and preferably 2 parts by weight with respect to 100 parts by weight of the cationic polymerizable compound.
  • the minimum with more preferable content of the said stabilizer is 0.05 weight part, and a more preferable upper limit is 1 weight part.
  • the sealing agent for organic EL display elements of the present invention may contain a silane coupling agent.
  • the said silane coupling agent has a role which improves the adhesiveness of the sealing agent for organic EL display elements of this invention, a board
  • silane coupling agent examples include 3-aminopropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-isocyanatopropyltrimethoxysilane, and the like. These silane coupling agents may be used independently and 2 or more types may be used together.
  • the content of the silane coupling agent is preferably 0.1 parts by weight and preferably 10 parts by weight with respect to 100 parts by weight of the cationic polymerizable compound.
  • the minimum with more preferable content of the said silane coupling agent is 0.5 weight part, and a more preferable upper limit is 5 weight part.
  • the sealing agent for organic EL display elements of the present invention may contain a surface modifier as long as the object of the present invention is not impaired.
  • a surface modifier By containing the surface modifier, the flatness of the coating film can be imparted to the organic EL display element sealant of the present invention.
  • the surface modifier include surfactants and leveling agents.
  • surfactant and the leveling agent examples include silicon-based, acrylic-based, and fluorine-based ones.
  • examples of commercially available surfactants and leveling agents include BYK-345, BYK-340 (both manufactured by Big Chemie Japan), Surflon S-611 (manufactured by AGC Seimi Chemical), and the like. Can be mentioned.
  • the encapsulant for organic EL display elements of the present invention may contain an ion exchange resin in order to improve the durability of the element electrode as long as the object of the present invention is not impaired.
  • any of a cation exchange type, an anion exchange type, and a both ion exchange type can be used, and in particular, a cation exchange type or a both ion exchange type capable of adsorbing chloride ions. Is preferred.
  • the sealing agent for organic EL display elements of this invention is a range which does not inhibit the objective of this invention, and is a hardening retarder, a reinforcing agent, a softener, a plasticizer, a viscosity modifier, and an ultraviolet absorber as needed. Further, various known additives such as antioxidants may be contained.
  • Examples of the method for producing the sealing agent for organic EL display elements of the present invention include a cationically polymerizable compound using a mixer such as a homodisper, a homomixer, a universal mixer, a planetary mixer, a kneader, or a three roll. And a method of mixing olefinic rubber particles, a cationic photopolymerization initiator, an alkaline earth metal-based and / or magnesium-based water-absorbing filler, and an additive to be added as necessary.
  • the olefin rubber particles may be previously dispersed in the cationic polymerizable compound and then mixed with other components.
  • the sealing agent for organic EL display elements of the present invention is intended for in-plane sealing
  • the preferred lower limit of the viscosity at 25 ° C. measured using an E-type viscometer is 50 mPa ⁇ s
  • the preferred upper limit is 8000 mPa ⁇ s. s.
  • the more preferable lower limit of the viscosity is 60 mPa ⁇ s
  • the more preferable upper limit is 3000 mPa ⁇ s
  • the still more preferable lower limit is 70 mPa ⁇ s
  • the still more preferable upper limit is 1000 mPa ⁇ s.
  • the viscosity is, for example, a VISCOMETER TV-22 (manufactured by Toki Sangyo Co., Ltd.) as an E-type viscometer, and a rotational speed of 1 to 100 rpm as appropriate from the optimum torque number in each viscosity region using a CP1 cone plate. Can be measured by selecting.
  • the sealing agent for organic EL display elements of the present invention aims at peripheral sealing
  • the preferred lower limit of viscosity at 25 ° C. measured with an E-type viscometer is 100 Pa ⁇ s
  • the preferred upper limit is 500 Pa ⁇ s. It is.
  • a more preferable lower limit of the viscosity is 200 Pa ⁇ s
  • a more preferable upper limit is 400 Pa ⁇ s
  • a still more preferable lower limit is 250 Pa ⁇ s
  • a still more preferable upper limit is 350 Pa ⁇ s.
  • the viscosity is, for example, a VISCOMETER TV-22 (manufactured by Toki Sangyo Co., Ltd.) as an E-type viscometer, and a rotational speed of 1 to 100 rpm as appropriate from the optimum torque number in each viscosity region using a CP7 cone plate. Can be measured by selecting.
  • the shape of the sealing portion formed in the organic EL display element sealant of the present invention is not particularly limited as long as it is a shape that can protect the laminate having the organic light emitting material layer from the outside air.
  • the shape may be completely covered, a closed pattern may be formed in the periphery of the laminate, or a pattern having a shape in which a part of the opening is provided in the periphery of the laminate is formed.
  • it can be suitably used for sealing the peripheral portion of the laminate.
  • the sealing compound for organic electroluminescent display elements which is excellent in the barrier property and toughness of hardened
  • 300 parts by weight of deionized water was put into a reaction vessel containing 1500 parts by weight of the latex (X-1) containing the polybutadiene rubber particles obtained, and stirred at 50 ° C. in a nitrogen atmosphere. Further, after adding 0.01 parts by weight of ethylenediaminetetraacetic acid disodium, 0.005 parts by weight of iron, and 0.24 parts by weight of sodium formaldehyde sulfoxylate, 90 parts by weight of methyl methacrylate as a graft monomer, t- 0.08 part by weight of butyl hydroperoxide was added over 2 hours to allow graft polymerization to proceed.
  • Polymerization was terminated after 2 hours from the start of the polymerization reaction, and a latex containing olefin rubber particles A having a core-shell structure was obtained.
  • the average particle diameter of the obtained olefin rubber particles A having a core-shell structure was 100 nm.
  • olefin rubber particles B having a core-shell structure instead of 100 parts by weight of butadiene, 75 parts by weight of butadiene and 25 parts by weight of styrene were added to the reaction vessel in the same manner as in “(Preparation of olefin rubber particles A having a core-shell structure)” above.
  • Olefin-based rubber particles B (average particle diameter of 100 nm) having a core-shell structure whose core layer is made of butadiene-styrene rubber were prepared.
  • Example 1 As cationically polymerizable compounds, 80 parts by weight of bisphenol F type epoxy resin (manufactured by DIC, “EPICLON EXA-830LVP”) and 20 parts by weight of solid bisphenol F type epoxy resin (manufactured by Mitsubishi Chemical Corporation, “jER 4005P”) Then, 50 parts by weight of the prepared olefin rubber particles A having a core-shell structure were added and stirred and mixed uniformly. Next, 1.0 part by weight of an aromatic iodonium salt (“PI2074” manufactured by Rhodia Co., Ltd.) as a photocationic polymerization initiator is added and dissolved by heating at 60 ° C. for 1 hour, and then 9,10-dibutoxy as a sensitizer.
  • PI2074 aromatic iodonium salt
  • Examples 2 to 12, Comparative Examples 1 to 5 Each material of the mixture ratio described in Table 1 and Table 2 was stirred and mixed in the same manner as in Example 1 to prepare an organic EL display element sealant.
  • Viscosity About each sealing agent for organic EL display elements obtained in Examples and Comparative Examples, the viscosity at 25 ° C. was measured using an E-type viscometer (manufactured by Toki Sangyo Co., Ltd., “VISCOMETER TV-22”). (Initial viscosity) was measured.
  • a glass substrate on which a glass substrate on which Ca is deposited is moved into a glow box controlled at a dew point ( ⁇ 60 ° C. or higher), and a sealing agent for each organic EL display element obtained in the examples and comparative examples is applied to the surface. Were pasted together. At this time, bonding was performed so that the deposited Ca exists at positions of 2 mm, 4 mm, and 6 mm from the end face of the glass substrate. Subsequently, ultraviolet rays of 365 nm were irradiated at 3000 mJ / cm 2 and further heated at 80 ° C. for 30 minutes to cure the sealing agent, thereby producing a Ca-TEST substrate.
  • the obtained Ca-TEST substrate was exposed to high-temperature and high-humidity conditions of 85 ° C. and 85% RH, and the moisture penetration distance per hour was observed from the disappearance of Ca.
  • ⁇ indicates that the time required for the moisture penetration distance to reach 6 mm is 1000 hours or more
  • ⁇ indicates that the time is 500 hours or more and less than 1000 hours
  • ⁇ indicates 100 hours or more and 500 hours.
  • x the barrier property of the cured product was evaluated.
  • a glass substrate (length 25 mm, width 25 mm, thickness 0.7 mm) on which an ITO electrode was formed to a thickness of 1000 mm was used as the substrate.
  • the substrate was ultrasonically washed with acetone, an aqueous alkali solution, ion-exchanged water, and isopropyl alcohol for 15 minutes, respectively, then washed with boiled isopropyl alcohol for 10 minutes, and a UV-ozone cleaner (manufactured by Nippon Laser Electronics Co., Ltd.). The last treatment was performed with “NL-UV253”).
  • this substrate is fixed to the substrate folder of the vacuum deposition apparatus, and 200 mg of N, N′-di (1-naphthyl) -N, N′-diphenylbenzidine ( ⁇ -NPD) is put into an unglazed crucible and other different types.
  • 200 mg of tris (8-quinolinolato) aluminum (Alq 3 ) was put in an unglazed crucible, and the inside of the vacuum chamber was depressurized to 1 ⁇ 10 ⁇ 4 Pa. Thereafter, the crucible containing ⁇ -NPD was heated, and ⁇ -NPD was deposited on the substrate at a deposition rate of 15 s / s to form a 600 ⁇ ⁇ hole transport layer.
  • the crucible containing Alq 3 was heated to form an organic light emitting material layer having a thickness of 600 ⁇ at a deposition rate of 15 ⁇ / s. Thereafter, the substrate on which the hole transport layer and the organic light emitting material layer are formed is transferred to another vacuum vapor deposition apparatus, and 200 mg of lithium fluoride is added to a tungsten resistance heating boat in the vacuum vapor deposition apparatus, and aluminum is added to another tungsten boat. 1.0 g of wire was added.
  • the inside of the vapor deposition unit of the vacuum vapor deposition apparatus is depressurized to 2 ⁇ 10 ⁇ 4 Pa to form a lithium fluoride film with a thickness of 5 mm at a deposition rate of 0.2 kg / s, and then aluminum with a film thickness of 1000 mm at a rate of 20 kg / s did.
  • the inside of the vapor deposition unit was returned to normal pressure with nitrogen, and the substrate on which the laminate having the organic light emitting material layer of 10 mm ⁇ 10 mm was arranged was taken out.
  • a mask having an opening of 13 mm ⁇ 13 mm was placed so as to cover the entire laminated body of the substrate on which the obtained laminated body was arranged, and an inorganic material film A was formed by a plasma CVD method.
  • SiH 4 gas and nitrogen gas are used as source gases, the flow rates of each are SiH 4 gas 10 sccm, nitrogen gas 200 sccm, RF power 10 W (frequency 2.45 GHz), chamber temperature 100 ° C., chamber The test was performed under the condition that the internal pressure was 0.9 Torr.
  • the formed inorganic material film A had a thickness of about 1 ⁇ m.
  • Vacuum deposition was performed so that Thereafter, ultraviolet rays having a wavelength of 365 nm were irradiated using a high pressure mercury lamp in a vacuum environment so that the irradiation amount was 3000 mJ / cm 2 to cure the organic EL display element sealant to form a resin protective film.
  • a mask having an opening of 12 mm ⁇ 12 mm is installed so as to cover the entire resin protective film, and the inorganic material film B is formed by plasma CVD to form an organic EL display element. Obtained.
  • SiH 4 gas and nitrogen gas are used as source gases, the flow rates of each are SiH 4 gas 10 sccm, nitrogen gas 200 sccm, RF power 10 W (frequency 2.45 GHz), chamber temperature 100 ° C., chamber The test was performed under the condition that the internal pressure was 0.9 Torr.
  • the formed inorganic material film B had a thickness of about 1 ⁇ m.
  • the sealing compound for organic electroluminescent display elements which is excellent in the barrier property and toughness of hardened

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)
  • Graft Or Block Polymers (AREA)

Abstract

L'invention a pour objet de fournir un agent d'encapsulation pour élément d'affichage électroluminescent organique tel que les propriétés de barrière et la dureté d'un objet durci sont excellentes. L'agent d'encapsulation pour élément d'affichage électroluminescent organique de l'invention comprend un composé polymérisable par voie cationique, des particules de caoutchouc à base d'oléfine, un initiateur de photopolymérisation par voie cationique, et une charge absorbant l'eau à base de métal alcalino-terreux et/ou de magnésium. Lesdites particules de caoutchouc à base d'oléfine présentent une structure cœur-coquille.
PCT/JP2016/055191 2015-02-24 2016-02-23 Agent d'encapsulation pour élément d'affichage électroluminescent organique WO2016136715A1 (fr)

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JP2016511838A JP6062107B1 (ja) 2015-02-24 2016-02-23 有機エレクトロルミネッセンス表示素子用封止剤
CN201680002382.9A CN106797685B (zh) 2015-02-24 2016-02-23 有机电致发光显示元件用密封剂
KR1020177001478A KR102641589B1 (ko) 2015-02-24 2016-02-23 유기 일렉트로루미네선스 표시 소자용 봉지제

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JP6294522B1 (ja) * 2017-02-14 2018-03-14 積水化学工業株式会社 有機ｅｌ表示素子用封止剤、及び、有機ｅｌ表示素子
WO2018052006A1 (fr) * 2016-09-16 2018-03-22 積水化学工業株式会社 Agent d'encapsulation pour élément d'affichage électroluminescent organique
JP2018095679A (ja) * 2016-12-08 2018-06-21 三井化学株式会社 シート状シール材、表示素子シール材、有機ｅｌ素子用面封止材、有機ｅｌデバイス、および有機ｅｌデバイスの製造方法

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WO2019004241A1 (fr) * 2017-06-28 2019-01-03 積水化学工業株式会社 Agent d'étanchéité dans le plan pour éléments d'affichage el organiques, et ensemble d'agents d'étanchéité pour éléments d'affichage el organiques

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CN108781491A (zh) * 2016-09-16 2018-11-09 积水化学工业株式会社 有机电致发光显示元件用密封剂
WO2018052006A1 (fr) * 2016-09-16 2018-03-22 積水化学工業株式会社 Agent d'encapsulation pour élément d'affichage électroluminescent organique
JPWO2018052006A1 (ja) * 2016-09-16 2019-06-27 積水化学工業株式会社 有機エレクトロルミネッセンス表示素子用封止剤
JP2018095679A (ja) * 2016-12-08 2018-06-21 三井化学株式会社 シート状シール材、表示素子シール材、有機ｅｌ素子用面封止材、有機ｅｌデバイス、および有機ｅｌデバイスの製造方法
JPWO2018151002A1 (ja) * 2017-02-14 2020-03-26 積水化学工業株式会社 光硬化性樹脂組成物、有機ｅｌ表示素子用封止剤、有機ｅｌ表示素子、量子ドットデバイス用封止剤、及び、量子ドットデバイス
CN109937214A (zh) * 2017-02-14 2019-06-25 积水化学工业株式会社 光固化性树脂组合物、有机el显示元件用密封剂、有机el显示元件、量子点设备用密封剂和量子点设备
WO2018151002A1 (fr) * 2017-02-14 2018-08-23 積水化学工業株式会社 Composition de résine photodurcissable, agent d'étanchéité pour éléments d'affichage électroluminescents organiques, élément d'affichage électroluminescent organique, agent d'étanchéité pour dispositifs à points quantiques et dispositif à points quantiques
KR20190135564A (ko) * 2017-02-14 2019-12-06 세키스이가가쿠 고교가부시키가이샤 광경화성 수지 조성물, 유기 el 표시 소자용 밀봉제, 유기 el 표시 소자, 양자 도트 디바이스용 밀봉제, 및 양자 도트 디바이스
JP6294522B1 (ja) * 2017-02-14 2018-03-14 積水化学工業株式会社 有機ｅｌ表示素子用封止剤、及び、有機ｅｌ表示素子
JP2020045371A (ja) * 2017-02-14 2020-03-26 積水化学工業株式会社 有機ｅｌ表示素子用封止剤、及び、有機ｅｌ表示素子
TWI750317B (zh) * 2017-02-14 2021-12-21 日商積水化學工業股份有限公司 光硬化性樹脂組成物、有機ｅｌ顯示元件用密封劑、有機ｅｌ顯示元件、量子點裝置用密封劑及量子點裝置
KR102355058B1 (ko) * 2017-02-14 2022-01-24 세키스이가가쿠 고교가부시키가이샤 광경화성 수지 조성물, 유기 el 표시 소자용 밀봉제, 유기 el 표시 소자, 양자 도트 디바이스용 밀봉제, 및 양자 도트 디바이스
KR20220010059A (ko) * 2017-02-14 2022-01-25 세키스이가가쿠 고교가부시키가이샤 광경화성 수지 조성물, 유기 el 표시 소자용 밀봉제, 유기 el 표시 소자, 양자 도트 디바이스용 밀봉제, 및 양자 도트 디바이스
CN114539479A (zh) * 2017-02-14 2022-05-27 积水化学工业株式会社 有机el显示元件用密封剂和有机el显示元件
CN109937214B (zh) * 2017-02-14 2022-10-21 积水化学工业株式会社 光固化性树脂组合物、有机el显示元件用密封剂、有机el显示元件、量子点设备用密封剂和量子点设备
KR102549655B1 (ko) * 2017-02-14 2023-06-30 세키스이가가쿠 고교가부시키가이샤 광경화성 수지 조성물, 유기 el 표시 소자용 밀봉제, 유기 el 표시 소자, 양자 도트 디바이스용 밀봉제, 및 양자 도트 디바이스

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KR20170120555A (ko) 2017-10-31
JP6062107B1 (ja) 2017-01-18

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