WO2023163113A1 - Agent d'encapsulation pour élément d'affichage électroluminescent organique, dispositif d'affichage électroluminescent organique et procédé de fabrication de dispositif d'affichage électroluminescent organique - Google Patents

Agent d'encapsulation pour élément d'affichage électroluminescent organique, dispositif d'affichage électroluminescent organique et procédé de fabrication de dispositif d'affichage électroluminescent organique Download PDF

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WO2023163113A1
WO2023163113A1 PCT/JP2023/006769 JP2023006769W WO2023163113A1 WO 2023163113 A1 WO2023163113 A1 WO 2023163113A1 JP 2023006769 W JP2023006769 W JP 2023006769W WO 2023163113 A1 WO2023163113 A1 WO 2023163113A1
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organic
compound
mass
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宙 宮尾
航太郎 舘野
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三井化学株式会社
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
    • C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
    • C08G65/16—Cyclic ethers having four or more ring atoms
    • C08G65/18—Oxetanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/07—Aldehydes; Ketones
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/13—Phenols; Phenolates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
    • C08K5/3472—Five-membered rings
    • C08K5/3475—Five-membered rings condensed with carbocyclic rings
    • 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
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
    • C08L71/02—Polyalkylene oxides
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/22—Absorbing filters
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L23/00—Details of semiconductor or other solid state devices
    • H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
    • H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L23/00—Details of semiconductor or other solid state devices
    • H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
    • H01L23/31—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the arrangement or shape
    • 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
    • H10K50/844—Encapsulations
    • 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
    • H10K59/10—OLED displays
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
    • H10K71/10—Deposition of organic active material
    • H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
    • H10K71/13—Deposition of organic active material using liquid deposition, e.g. spin coating using printing techniques, e.g. ink-jet printing or screen printing
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/40—Interrelation of parameters between multiple constituent active layers or sublayers, e.g. HOMO values in adjacent layers

Definitions

  • the present invention relates to a sealing material for an organic EL display element, an organic EL display device, and a method for manufacturing an organic EL display device.
  • an organic EL display has been known as an image display device equipped with optical elements.
  • the optical elements are sealed with a sealing layer in order to prevent deterioration of the optical elements due to moisture in the atmosphere.
  • the sealing layer is formed, for example, by embedding an optical element in a sealing composition and then curing the sealing composition by light irradiation.
  • a sealing composition for example, a sealant for an organic EL display element containing a cationic polymerizable compound, a polymerization initiator, and a benzotriazole compound has been proposed (for example, the implementation of Patent Document 1 See Example 1).
  • the sealant for organic EL display elements of Patent Document 1 acid is generated from the polymerization initiator (photoacid generator) even under weak light such as from a fluorescent lamp. Then, the acid is not deactivated as it is, and the polymerization (curing) of the sealant for organic EL display elements progresses and the viscosity increases. In other words, the sealant for organic EL display elements of Patent Document 1 has a problem of low stability against white light.
  • a cured product of such a sealing composition is required to have reliability.
  • the present invention provides a sealing material for an organic EL display element that is excellent in stability against white light and reliability after curing, and an organic sealing layer comprising a cured product of the sealing material for an organic EL display element.
  • An EL display device and a method for manufacturing an organic EL display device are provided.
  • the present invention [1] includes a cationic polymerizable compound, a cationic polymerization initiator, an ultraviolet absorber, and a compound having a phenolic hydroxyl group, and the mass of the compound having a phenolic hydroxyl group relative to the ultraviolet absorber.
  • the encapsulant for organic EL display elements has a ratio (compound having a phenolic hydroxyl group/ultraviolet absorber) of 0.01 or more and less than 1.00.
  • the present invention [2] includes the sealant for organic EL display elements according to the above [1], wherein the cationic polymerizable compound is an epoxy compound and/or an oxetane compound.
  • the present invention [3] includes the encapsulant for organic EL display elements according to the above [1] or [2], wherein the ultraviolet absorber is a benzotriazole compound or a benzophenone compound.
  • the present invention [4] is the organic EL display element according to any one of the above [1] to [3], wherein the content of the ultraviolet absorber is 0.1% by mass or more and 2% by mass or less. Contains an encapsulant for
  • the present invention [5] is according to any one of the above [1] to [4], wherein the content of the compound having a phenolic hydroxyl group is 0.01% by mass or more and 0.5% by mass or less. of organic EL display element sealing material.
  • the present invention [6] is for an organic EL display element according to any one of the above [1] to [5], which is liquid at 25° C. and has a solvent content of 0.05% by mass or less. Contains encapsulant.
  • the present invention [7] is the sealing material for organic EL display elements according to any one of the above [1] to [6], wherein the viscosity at 25° C. is 5 mPa ⁇ s or more and 50 mPa ⁇ s or less. contains.
  • the present invention [8] comprises a substrate, an organic EL element mounted on one side in the thickness direction of the substrate, and a sealing layer covering the organic EL element, wherein the sealing layer comprises the above [1]
  • An organic EL display device comprising a cured product of the sealing material for an organic EL display device according to any one of [7].
  • the present invention [9] comprises a first step of preparing a substrate, a second step of mounting an organic EL element on one side in the thickness direction of the substrate, and a sealing layer covering the organic EL element by an inkjet method. and a third step of forming the organic EL display, wherein the sealing layer is made of a cured product of the sealing material for an organic EL display element according to any one of [1] to [7] above. It includes a method of manufacturing the device.
  • the mass ratio of the compound having a phenolic hydroxyl group to the ultraviolet absorber is 0.01 to 1.00. is less than In this sealing material for an organic EL display element, since the mass ratio is 0.01 or more, the stability against white light can be improved. Moreover, in this sealing material for organic EL display elements, since the mass ratio is less than 1.00, the reliability after curing can be improved.
  • the organic EL element is covered with a sealing layer made of a cured product of the organic EL display element sealing material of the present invention. Therefore, it is highly reliable.
  • the organic EL element is coated by an inkjet method, and a sealing layer made of a cured product of the sealing material for an organic EL display element of the present invention is formed. Therefore, an organic EL display device with excellent reliability can be manufactured.
  • FIG. 1 shows a cross-sectional view of one embodiment of the organic EL display device of the present invention.
  • 2A to 2C are schematic diagrams showing an embodiment of the method for manufacturing an organic EL display device of the present invention.
  • FIG. 2A shows the first step of preparing the substrate.
  • FIG. 2B shows the second step of mounting the organic EL element on one surface in the thickness direction of the substrate.
  • FIG. 2C shows the third step of forming the sealing layer 3 covering the organic EL element 2 by the inkjet method.
  • a sealing material for an organic EL display element contains a cationic polymerizable compound, a cationic polymerization initiator, an ultraviolet absorber, and a compound having a phenolic hydroxyl group.
  • Cationically polymerizable compounds include, for example, epoxy compounds and oxetane compounds. That is, the cationically polymerizable compound is preferably an epoxy compound and/or an oxetane compound. More preferably, the cationically polymerizable compounds are epoxy compounds and oxetane compounds.
  • Epoxy compounds include, for example, alicyclic epoxy resins, aliphatic epoxy resins, and aromatic epoxy resins, preferably alicyclic epoxy resins and aliphatic epoxy resins. More preferably, the epoxy compound comprises an alicyclic epoxy resin and an aliphatic epoxy resin, and even more preferably, the epoxy compound consists of an alicyclic epoxy resin and an aliphatic epoxy resin.
  • the alicyclic epoxy resin is a curable resin (photocurable resin, preferably ultraviolet curable resin) having an epoxy group and an alicyclic ring (alicyclic skeleton) and no aromatic ring.
  • alicyclic epoxy resins examples include glycidyl group-containing alicyclic epoxy resins, glycidyl ether group-containing alicyclic epoxy resins, and epoxycyclo structure-containing epoxy resins.
  • a glycidyl group-containing alicyclic epoxy resin has, for example, a glycidyl group bonded to an alicyclic ring.
  • Such a glycidyl group-containing alicyclic epoxy resin is represented, for example, by the following general formula (1).
  • R1 represents a monovalent organic group and n represents the degree of polymerization. Further, a substituent such as an alkyl group may be bonded to the carbon atoms constituting the cyclohexane ring.
  • glycidyl group-containing alicyclic epoxy resin represented by the general formula (1) specifically, 1,2-epoxy-4-(2-oxiranyl of 2,2-bis(hydroxymethyl)-1-butanol ) cyclohexane adducts.
  • a commercially available product can also be used as the glycidyl group-containing alicyclic epoxy resin represented by the general formula (1).
  • Examples of commercially available products of the glycidyl group-containing alicyclic epoxy resin represented by the general formula (1) include EHPE3150 (epoxy equivalent: 170 to 190 g/eq., manufactured by Daicel).
  • a glycidyl ether group-containing alicyclic epoxy resin has a glycidyl ether unit bonded to an alicyclic ring.
  • the glycidyl ether group-containing alicyclic epoxy resin is a polyglycidyl ether-containing alicyclic epoxy resin having a plurality of glycidyl ether units bonded to an alicyclic ring.
  • glycidyl ether-containing alicyclic epoxy resins examples include bifunctional glycidyl ether-containing alicyclic epoxy resins.
  • Bifunctional glycidyl ether-containing alicyclic epoxy resins include, for example, hydrogenated bisphenol A diglycidyl ether, hydrogenated bisphenol F diglycidyl ether, and hexahydrophthalic acid diglycidyl ester.
  • the epoxy cyclo structure-containing epoxy resin has an epoxy cyclo structure having an epoxy group composed of two adjacent carbon atoms forming an alicyclic ring and one oxygen atom bonded to the two carbon atoms. .
  • epoxy cyclo structure-containing epoxy resins examples include epoxy cyclohexane structure-containing epoxy resins (hereinafter referred to as ECH structure-containing epoxy resins).
  • ECH structure-containing epoxy resins examples include epoxy resins containing one ECH structure represented by the following chemical formula (2), epoxy resins containing two ECH structures represented by the following general formula (3), and their Modified products are mentioned.
  • X represents a linking group (a divalent group having one or more atoms).
  • m represents 0 or 1;
  • R2 represents one atom or substituent selected from the group consisting of a hydrogen atom, a fluorine atom, an alkyl group, a fluoroalkyl group, an aryl group, a furyl group and a thienyl group.
  • Two R2's in formula (3) may be the same or different.
  • the epoxy resin containing two ECH structures represented by the general formula (3) (hereinafter referred to as the ECH structure-containing epoxy resin represented by the general formula (3)) has an ECH structure (epoxycyclohexyl group) in the molecule It has two epoxycyclohexyl groups at both ends, and two epoxycyclohexyl groups are linked via a linking group (a carbon-carbon bond when m is 0).
  • the epoxycyclohexyl group is a functional group containing a cyclohexane ring, an epoxy group composed of two adjacent carbon atoms forming the cyclohexane ring, and one oxygen atom bonded to the two carbon atoms. is.
  • the alkyl group represented by R2 in the general formula (3) includes, for example, a linear or branched alkyl group having 1 to 6 carbon atoms (e.g., methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, etc.).
  • fluoroalkyl group represented by R2 in the general formula (3) for example, a linear or branched fluoroalkyl group having 1 to 6 carbon atoms (e.g., perfluoromethyl group, perfluoroethyl group, perfluoropropyl group, etc.).
  • Examples of the aryl group represented by R2 in the above general formula (3) include aryl groups having 6 to 18 carbon atoms (eg, phenyl group, naphthyl group, etc.).
  • Examples of the linking group represented by X in the general formula (3) include an oxygen atom, a sulfur atom, a divalent hydrocarbon group, a polyoxyalkylene group, a carbonyl group, an ether group, a thioether group, an ester group, a carbonate group, Examples include amide groups and groups in which these groups are linked. Note that when m is 0, two ECH structures are linked via a carbon-carbon bond.
  • divalent hydrocarbon groups examples include linear or branched alkylene groups having 1 to 20 carbon atoms (e.g., methylene group, methylmethylene group, dimethylmethylene group, ethylene group, propylene group, trimethylene group, butylene group, etc.), linear or branched unsaturated hydrocarbon groups having 1 to 20 carbon atoms (eg, propenylene group, methylpropenylene group, butenylene group, etc.), and the like.
  • linear or branched alkylene groups having 1 to 20 carbon atoms e.g., methylene group, methylmethylene group, dimethylmethylene group, ethylene group, propylene group, trimethylene group, butylene group, etc.
  • linear or branched unsaturated hydrocarbon groups having 1 to 20 carbon atoms eg, propenylene group, methylpropenylene group, butenylene group, etc.
  • polyoxyalkylene groups include linear or branched polyoxyalkylene groups having 1 to 120 carbon atoms (eg, polyoxyethylene groups, polyoxypropylene groups, etc.).
  • ECH structure-containing epoxy resins represented by general formula (3) include (3,3′,4,4′-diepoxy)bicyclohexyl, bis(3,4-epoxycyclohexylmethyl)ether, 1, 2-bis(3,4-epoxycyclohexan-1-yl)ethane, 2,2-bis(3,4-epoxycyclohexan-1-yl)propane, 3,4-epoxycyclohexylmethyl (3,4-epoxy) Cyclohexanecarboxylate and ⁇ -caprolactone-modified 3′,4′-epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate, preferably (3,3′,4,4′-diepoxy)bicyclohexyl (In formula (3) above, m represents 0 and R2 represents a hydrogen atom.).
  • a commercially available product can also be used as the ECH structure-containing epoxy resin represented by the general formula (3).
  • Examples of commercially available ECH structure-containing epoxy resins represented by the general formula (3) include Celoxide 8000, Celoxide 8010, Celoxide 2021P, and Celoxide 2081 (manufactured by Daicel Corporation).
  • the ECH structure-containing epoxy resin preferably includes the ECH structure-containing epoxy resin represented by the above general formula (3).
  • an epoxy cyclo structure-containing epoxy resin is preferably used.
  • the weight average molecular weight of the alicyclic epoxy resin is, for example, 200 or more and, for example, 1000 or less, preferably 500 or less.
  • the weight average molecular weight (Mw) can be determined by gel permeation chromatography (GPC) using polystyrene as a standard (the same applies hereinafter).
  • the epoxy equivalent of the alicyclic epoxy resin is, for example, 90 g/eq. above, preferably 100 g/eq. Above, for example, 250 g/eq. Below, preferably 190 g/eq. It is below.
  • the epoxy equivalent can be measured according to JIS K7236:2001 (the same applies hereinafter).
  • Aliphatic epoxy resins include, for example, bifunctional aliphatic epoxy resins.
  • Difunctional aliphatic epoxy resins include, for example, ethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, 1,6-hexanediol diglycidyl ether, and neopentyl glycol diglycidyl ether, preferably neo Pentyl glycol diglycidyl ether may be mentioned.
  • the weight average molecular weight of the aliphatic epoxy resin is, for example, 150 or more and, for example, 400 or less.
  • the epoxy equivalent of the aliphatic epoxy resin is, for example, 60 g/eq. above, and for example, 250 g/eq. It is below.
  • the content of the alicyclic epoxy resin is, for example, , 10 parts by mass or more, preferably 20 parts by mass or more, and for example, 50 parts by mass or less, preferably 40 parts by mass or less.
  • the content of the alicyclic epoxy resin is, for example, 5% by mass or more, preferably 10% by mass or more, and for example, 30% by mass or less, preferably 20% by mass, relative to the cationic polymerizable compound. It is below.
  • the content of the aliphatic epoxy resin is For example, it is 40 parts by mass or more, preferably 50 parts by mass or more, more preferably 60 parts by mass or more, and for example, 90 parts by mass or less, preferably 80 parts by mass or less. Further, the content of the aliphatic epoxy resin is, for example, 20% by mass or more, preferably 30% by mass or more, and for example, 50% by mass or less, preferably 40% by mass or less, relative to the cationic polymerizable compound. is.
  • Epoxy compounds can be used alone or in combination of two or more.
  • the content of the epoxy compound is, for example, 30% by mass or more, preferably 40% by mass or more, and for example, 70% by mass or less, preferably 60% by mass or less, relative to the cationic polymerizable compound. .
  • the oxetane compound contains, for example, from 1 to 5 oxetane rings.
  • oxetane compounds include monofunctional oxetane compounds having one oxetane ring, bifunctional oxetane compounds having two oxetane rings, and trifunctional or higher oxetane compounds having three or more oxetane rings.
  • Examples of monofunctional oxetane compounds include 3-ethyl-3-hydroxymethyloxetane, 3-(meth)allyloxymethyl-3-ethyloxetane, (3-ethyl-3-oxetanylmethoxy)methylbenzene, 2-ethylhexyl (3 -ethyl-3-oxetanylmethyl)ether, ethyldiethylene glycol (3-ethyl-3-oxetanylmethyl)ether, and 3-cyclohexylmethyl-3-ethyl-oxetane.
  • bifunctional oxetane compounds include 1,4-bis ⁇ [(3-ethyl-3-oxetanyl)methoxy]methyl ⁇ benzene, 3,3′-(oxybismethylene)bis(3-ethyloxetane), 1, 4-bis[(3-ethyl-3-oxetanyl)methoxy]benzene, 1,3-bis[(3-ethyl-3-oxetanyl)methoxy]benzene, 3,7-bis(3-oxetanyl)-5-oxa -nonane, 1,4-bis[(3-ethyl-3-oxetanylmethoxy)methyl]benzene, 1,2-bis[(3-ethyl-3-oxetanylmethoxy)methyl]ethane, 1,2-bis[( 3-ethyl-3-oxetanylmethoxy)methyl]propane, ethylene glycol bis(3-ethyl-3-oxe
  • trifunctional or higher oxetane compounds include trimethylolpropane tris(3-ethyl-3-oxetanylmethyl) ether, pentaerythritol tris(3-ethyl-3-oxetanylmethyl) ether, pentaerythritol tetrakis(3-ethyl-3 -oxetanylmethyl) ether, and dipentaerythritol pentakis(3-ethyl-3-oxetanylmethyl) ether.
  • oxetane compounds can also be used.
  • examples of commercially available oxetane compounds include Aron oxetane OXT-221 (3,3'-(oxybismethylene)bis(3-ethyloxetane)) and Aron oxetane OXT-121 (manufactured by Toagosei Chemical Co., Ltd.). .
  • the oxetane compound preferably includes a bifunctional oxetane compound.
  • the oxetane compound can be used alone or in combination of two or more.
  • the content of the oxetane compound is, for example, 30% by mass or more, preferably 40% by mass or more, and for example, 70% by mass or less, preferably 60% by mass or less, relative to the cationic polymerizable compound.
  • the content of the cationic polymerizable compound is, for example, 80% by mass or more, preferably 90% by mass or more, and, for example, 98% by mass or less with respect to the sealing material for organic EL display elements.
  • a cationic polymerization initiator is, for example, a photoacid generator that generates an acid upon irradiation with light.
  • the cationic polymerization initiator is not particularly limited, and known cationic polymerization initiators can be used.
  • the cationic polymerization initiator can be used alone or in combination of two or more.
  • the content of the cationic polymerization initiator is, for 100 parts by mass of the cationic polymerizable compound, for example, 0.5 parts by mass or more, preferably 0.8 parts by mass or more, more preferably 1.3 parts by mass or more, Also, for example, it is 5 parts by mass or less, preferably 2.5 parts by mass or less.
  • the content of the cationic polymerization initiator is, for example, 0.5% by mass or more, preferably 1% by mass or more, and, for example, 10% by mass or less, relative to the sealing material for organic EL display elements. Preferably, it is 5% by mass or less.
  • the ultraviolet absorber is a component that absorbs white light and suppresses the generation of acid from the cationic polymerization initiator.
  • ultraviolet absorbers examples include benzotriazole compounds, benzophenone compounds, triazine compounds, and cyanoacrylate compounds.
  • Benzotriazole compounds include, for example, 2-(5-methyl-2-hydroxyphenyl)benzotriazole, 2,2-hydroxy-3,5-bis( ⁇ , ⁇ -dimethylbenzyl)phenyl, 2-(2′- hydroxy-5′-methyl-phenyl)benzotriazole, 2-(2′-hydroxy-3′,5′-di-t-butyl-phenyl)benzotriazole, 2-(2′-hydroxy-3′-t- Butyl-5′-methyl-phenyl)-5-chloro benzotriazole, 2-(2′-hydroxy-3′,5′-di-t-butyl-phenyl)-5-chloro benzotriazole, 2-( 2H-benzotriazol-2-yl)-4,6-bis(1-methyl-1-phenylethyl)-phenol, 2-(2-hydroxy-5-methylphenyl)benzotriazole, and 2-(2' -hydroxy-4'-n-octoxyphenyl)benzotri
  • a commercially available product can also be used as the benzotriazole compound.
  • benzotriazole compounds include Tinuvin 234 (2-(2H-benzotriazol-2-yl)-4,6-bis(1-methyl-1-phenylethyl)-phenol, manufactured by BASF Japan Ltd.). , KEMISORB71 (2-(2-hydroxy-5-methylphenyl)benzotriazole, manufactured by Chemipro Kasei Co., Ltd.), and RUVA-93 (2-[2-hydroxy-5-[2-(methacryloyloxy)ethyl]phenyl] -2H-benzotriazole, manufactured by Otsuka Chemical Co., Ltd.).
  • benzophenone compounds include [2-hydroxy-4-(octyloxy)phenyl](phenyl)methanone, 2-hydroxy-4-n-octyloxybenzophenone, 2,4-dihydroxybenzophenone, 2-hydroxy-4 -methoxy benzophenone, 2,2'-dihydroxy-4-methoxy benzophenone, 2,2'-dihydroxy-4,4'-dimethoxy benzophenone, 2,2'-dihydroxy-4,4'-dimethoxy-5- Sulfobenzophenone, 2-hydroxy-4-methoxy-2'-carboxy benzophenone, 2-hydroxy-4-methoxy-5-sulfobenzophenone trihydrate, 2-hydroxy-4-n-dodecyloxy benzophenone, 2-hydroxy -4-benzyloxybenzophenone, 2,2',4,4'-tetrahydroxy benzophenone, 2-hydroxy-4-dodecyloxy-benzophenone, and 2-hydroxy-4-(2-hydroxy-3-me
  • a commercially available product can also be used as the benzophenone compound.
  • Commercially available benzophenone compounds include, for example, KEMIISORB12 (2-hydroxy-4-n-octyloxybenzophenone, manufactured by Chemipro Kasei Co., Ltd.) and Adekastab 1413 ([2-hydroxy-4-(octyloxy)phenyl](phenyl) Methanone, manufactured by ADEKA).
  • triazine compounds include 2-[4,6-di(2,4-xylyl)-1,3,5-triazin-2-yl]-5-octyloxyphenol and 2,4-diphenyl- 6-(2-hydroxy-4-hexyloxyphenyl)-1,3,5-triazines, preferably 2,4-diphenyl-6-(2-hydroxy-4-hexyloxyphenyl)-1, 3,5-triazines are mentioned.
  • a commercially available product can also be used as the triazine compound.
  • Examples of commercially available triazine compounds include KEMISORB102 (2,4-diphenyl-6-(2-hydroxy-4-hexyloxyphenyl)-1,3,5-triazine, manufactured by Chemipro Kasei).
  • cyanoacrylate compounds include ethyl-2-cyano-3-(3',4'-methylenedioxyphenyl)-acrylate.
  • the UV absorber preferably a benzotriazole compound, a benzophenone compound, and a triazine compound, more preferably a benzotriazole compound and a benzophenone compound, more preferably as a UV absorber, a benzotriazole compound or benzophenone.
  • a compound is selected.
  • the UV absorber is a benzotriazole compound or a benzophenone compound, the stability against white light is even better.
  • the ultraviolet absorber is a benzotriazole compound from the viewpoint of further improving the stability against white light.
  • the ultraviolet absorbers can be used alone or in combination of two or more.
  • the content of the ultraviolet absorber is, for example, 0.05 parts by mass or more, preferably 0.4 parts by mass or more, more preferably 0.8 parts by mass or more with respect to 100 parts by mass of the cationic polymerizable compound, and , for example, 2 parts by mass or less, preferably 1.5 parts by mass or less.
  • the content of the ultraviolet absorber is, for example, 0.1% by mass or more, preferably 0.5% by mass or more, more preferably 0.8% by mass, relative to the sealing material for organic EL display elements. % or more, and for example, 2% by mass or less, preferably 1.5% by mass or less, more preferably 1.5% by mass or less, from the viewpoint of improving the reliability of the sealing material for organic EL display elements after curing. It is 2% by mass or less.
  • the content of the ultraviolet absorber is equal to or higher than the above lower limit, the stability against white light can be improved.
  • the content of the ultraviolet absorber is equal to or less than the above upper limit, the curability when cured by irradiation with ultraviolet rays is maintained.
  • a compound having a phenolic hydroxyl group is a component that scavenges an acid generated from a cationic polymerization initiator upon irradiation with light.
  • a compound having a phenolic hydroxyl group is a compound having one or more phenolic hydroxyl groups in the molecule. Further, the compounds having a phenolic hydroxyl group do not include the above benzotriazole compounds, the above benzophenone compounds, the above triazine compounds, and the above cyanoacrylate compounds.
  • a compound having a phenolic hydroxyl group preferably a compound having a monofunctional phenolic hydroxyl group having one benzene ring, the benzene ring having one phenolic hydroxyl group, one benzene ring and a compound having a bifunctional phenolic hydroxyl group in which the benzene ring has two phenolic hydroxyl groups, and a compound having one benzene ring, in which the benzene ring has three or more phenolic hydroxyl groups compounds having a trifunctional or higher phenolic hydroxyl group. That is, a compound having a phenolic hydroxyl group preferably has one benzene ring. This ensures excellent stability.
  • Examples of compounds having a monofunctional phenolic hydroxyl group include compounds represented by the following formula (4).
  • R3 represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an alkyl ester group.
  • alkyl groups having 1 to 10 carbon atoms Indicates an alkyl group having 1 to 10 carbon atoms.
  • alkyl groups having 1 to 10 carbon atoms include methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group and decyl group.
  • R4 represents an alkylene group having 1 to 6 carbon atoms.
  • alkylene group having 1 to 6 carbon atoms include methylene group, methylmethylene group, dimethylmethylene group, ethylene group, propylene group, trimethylene group and butylene group.
  • R5 represents an alkyl group having 1 to 10 carbon atoms.
  • alkyl groups having 1 to 10 carbon atoms include methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group and decyl group.
  • a compound having a monofunctional phenolic hydroxyl group preferably 2,6-di-tert-butyl-p-cresol (a compound in which R3 represents a methyl group in the above formula (4)), and Benzenepropanoic acid 3,5-bis(1,1-dimethylethyl)-4-hydroxy-C7-C9 side chain alkyl ester (in the above formula (4), R3 represents an alkyl ester group, the above formula (5) , a compound in which R4 represents an ethylene group and R5 represents a heptyl group, a compound in which R4 represents an ethylene group and R5 represents an octyl group, and a compound in which R4 represents an ethylene group and R5 represents a nonyl group. mixture), preferably 2,6-di-tert-butyl-p-cresol.
  • the compound represented by formula (4) above preferably does not contain an alkyl ester group. Therefore, since the contribution of the addition amount to the stability of white light is high, it is even more excellent from the viewpoint of compatibility between the stability of white light and curability.
  • Examples of compounds having a bifunctional phenolic hydroxyl group include hydroquinone, resorcinol, tert-butylcatechol, and tert-butylhydroquinone.
  • Examples of compounds having trifunctional or higher phenolic hydroxyl groups include pyrogallol.
  • the compound having a phenolic hydroxyl group preferably a compound having a monofunctional phenolic hydroxyl group and a compound having a bifunctional phenolic hydroxyl group, more preferably a compound having both stability and curability to white light
  • a compound having a monofunctional phenolic hydroxyl group can be mentioned.
  • the molecular weight of the compound having a phenolic hydroxyl group is, for example, 94 or more, preferably 100 or more, more preferably 200 or more, and for example, 1000 or less, preferably 500 or less, stability against white light and From the viewpoint of compatibility with curability, it is more preferably 300 or less.
  • the molecular weight is low, the contribution of the amount added to the stability of white light is high, so it is even more excellent from the viewpoint of compatibility between the stability of white light and curability.
  • a compound having a phenolic hydroxyl group can be used alone or in combination of two or more.
  • the content of the compound having a phenolic hydroxyl group is, for example, 0.01 parts by mass or more, preferably 0.05 parts by mass or more, more preferably 0.08 parts by mass with respect to 100 parts by mass of the cationic polymerizable compound. parts or more, more preferably 0.1 parts by mass or more, and for example, 0.5 parts by mass or less, preferably 0.3 parts by mass or less, more preferably 0.15 parts by mass or less.
  • the content of the compound having a phenolic hydroxyl group is, for example, 0.01% by mass or more, preferably 0.05% by mass or more, more preferably 0.05% by mass or more, and more preferably 0.08% by mass or more, more preferably 0.1% by mass or more, and for example, 0.5% by mass or less, preferably 0.3% by mass or less, more preferably 0.15% by mass or less be.
  • the content of the compound having a phenolic hydroxyl group is at least the above lower limit, the stability against white light can be improved.
  • the curability is excellent.
  • the mass ratio of the compound having a phenolic hydroxyl group to the ultraviolet absorber is 0.01 or more, preferably 0.03 or more, more preferably 0.03 or more. 07 or more, more preferably 0.09 or more, particularly preferably 0.1 or more, and less than 1.00, preferably 0.5 or less, more preferably 0.3 or less, further preferably 0 .2 or less.
  • the mass ratio is equal to or higher than the lower limit, the stability against white light can be improved.
  • the mass ratio is less than the lower limit, the stability against white light is lowered.
  • the mass ratio is equal to or less than the upper limit, the reliability of the sealing material for organic EL display elements is excellent.
  • a sealant for an organic EL display element To prepare a sealant for an organic EL display element, first, a cationically polymerizable compound, a cationically polymerizable compound, an ultraviolet absorber, and a compound having a phenolic hydroxyl group are mixed to prepare a mixture. Next, a cationic polymerization initiator is added to this mixture and mixed. This prepares the sealing material for organic EL display elements.
  • the sealing material for organic EL display elements can also contain an additive.
  • Additives include, for example, sensitizers, tackifiers, antioxidants, polymerization initiation aids, anti-aging agents, wettability improvers, surfactants, plasticizers, ultraviolet absorbers, preservatives, and antibacterial agents.
  • the blending ratio of additives is appropriately set according to the application and purpose.
  • Additives can be used singly or in combination of two or more.
  • the organic EL display element sealing material may contain a solvent, but preferably the organic EL display element sealing material does not substantially contain a solvent.
  • the solvent content is, for example, 0.05% by mass or less, preferably 0.01% by mass or less, and more preferably 0.001% by mass or less.
  • the organic EL display element sealing material is preferably liquid at 25°C. Being liquid at 25°C is defined as having a viscosity of 5 mPa ⁇ s or more and 50 mPa ⁇ s or less at 25°C. If the sealing material for organic EL display elements is liquid at 25° C., it is excellent in jettability by inkjet.
  • the viscosity at 25° C. is, for example, 1 mPa s or more, preferably 5 mPa s or more, more preferably 10 mPa s or more, and for example, 50 mPa s or less, preferably , 30 mPa ⁇ s or less, more preferably 25 mPa ⁇ s or less.
  • the cured product of the sealing material for organic EL display elements preferably has transparency.
  • the total light transmittance (in accordance with JIS K 7361-1) of the cured product of the sealing material for organic EL display elements is, for example, 80% or more, preferably 85% or more, and more preferably 90% or more and, for example, 100% or less.
  • the mass ratio of the compound having a phenolic hydroxyl group to the ultraviolet absorber is 0.01 or more and less than 1.00. be.
  • the mass ratio is 0.01 or more, the stability against white light can be improved.
  • the mass ratio is less than 1.00, the reliability of the cured organic EL element can be improved from the viewpoint of curability.
  • a sealing material for organic EL display elements has excellent stability against white light and excellent reliability after curing, it can be suitably used as a sealing material for organic EL display elements. .
  • this organic EL display element sealing material has stability against white light, thickening is suppressed. Therefore, it can be suitably used in the inkjet method.
  • a cationically polymerizable compound, a cationically polymerizable compound, an ultraviolet absorber, and a compound having a phenolic hydroxyl group are mixed, and the mixture is After preparing this mixture, a cationic polymerization initiator is blended, but the cationic polymerization initiator can be blended together with the cationic polymerizable compound, the ultraviolet absorber, and the compound having a phenolic hydroxyl group.
  • Organic EL display device One embodiment of the organic EL display device of the present invention will be described with reference to FIG.
  • the organic EL display device 10 includes a substrate 1 , an organic EL element 2 mounted on one surface of the substrate 1 in the thickness direction, and a sealing layer 3 covering the organic EL element 2 .
  • a substrate 1 supports an organic EL element 2 .
  • Examples of the substrate 1 include glass substrates and plastic substrates, preferably glass substrates.
  • the thickness of the substrate 1 is, for example, 0.1 mm or more and, for example, 20 mm or less.
  • the organic EL element 2 is a known organic EL element and mounted on the substrate 1 .
  • the organic EL element 2 includes a cathode reflective electrode, an organic EL layer, and an anode transparent electrode (not shown).
  • the sealing layer 3 is a layer for suppressing deterioration of the organic EL element 2 due to moisture in the atmosphere.
  • the sealing layer 3 is made of a cured product of the above-described organic EL display element sealing material.
  • the thickness of the sealing layer 3 is, for example, 1 ⁇ m or more and, for example, 100 ⁇ m or less.
  • the method for manufacturing an organic EL display device includes a first step of preparing a substrate 1, a second step of mounting an organic EL element 2 on one side in the thickness direction of the substrate 1, and coating the organic EL element 2 by an inkjet method. and a third step of forming the sealing layer 3 to be formed.
  • a substrate 1 is prepared as shown in FIG. 2A.
  • the organic EL element 2 is mounted on one surface of the substrate 1 in the thickness direction by, for example, a known method (eg, vacuum deposition method).
  • the sealing layer 3 that covers the organic EL element 2 is formed by the inkjet method. According to the inkjet method, the organic EL element 2 can be reliably sealed.
  • the organic EL display element sealing material is arranged so as to cover the organic EL element 2 by an inkjet method. Thereafter, the organic EL display element sealing material is irradiated with light to cure the organic EL display element sealing material. Thus, the organic EL display device 10 is manufactured.
  • the organic EL elements 2 are covered with a sealing layer 3 made of a cured product of a highly reliable organic EL display element sealing material. Therefore, it is highly reliable.
  • the manufacturing method of the organic EL display device includes forming the sealing layer 3 which covers the organic EL element 2 and is made of a cured product of a highly reliable sealing material for an organic EL display element by an inkjet method. . Therefore, the organic EL display device 10 having excellent reliability can be manufactured.
  • the organic EL display device 10 can be provided with another sealing layer (for example, an inorganic sealing layer) on one side in the thickness direction and/or the other side in the thickness direction.
  • another sealing layer for example, an inorganic sealing layer
  • CEL8010 (3,3′,4,4′-diepoxy)bicyclohexyl, trade name “Celoxide 8010”, Daicel NPG (G): neopentyl glycol diglycidyl ether, Sakamoto Yakuhin Kogyo OXT221: 3,3 '-(Oxybismethylene)bis(3-ethyloxetane), trade name "Aronoxetane OXT-221", Tinuvin234 manufactured by Toagosei Chemical Co., Ltd.: 2-(2H-benzotriazol-2-yl)-4,6-bis (1-methyl-1-phenylethyl)-phenol, BASF Japan Ltd.
  • KEMIISORB71 2-(2-hydroxy-5-methylphenyl) benzotriazole
  • Chemipro Kasei Co., Ltd. RUVA-93 2-[2-hydroxy- 5-[2-(Methacryloyloxy)ethyl]phenyl]-2H-benzotriazole
  • KEMIISORB12 manufactured by Otsuka Chemical Co., Ltd.: 2-hydroxy-4-n-octyloxybenzophenone
  • Adekastab 1413 manufactured by Chemipro Kasei Co., Ltd.: [2-Hydroxy-4 -(Octyloxy)phenyl](phenyl)methanone
  • ADEKA KEMIISORB102 2,4-diphenyl-6-(2-hydroxy-4-hexyloxyphenyl)-1,3,5-triazine
  • Chemipro Kasei BHT 2,6-di-tert-butyl-p-cresol
  • molecular weight 220 Irganox 1135 Benz
  • the stability to white light was evaluated based on the following criteria. Table 1 shows the results. Good: The viscosity increase rate was less than 20%. ⁇ : The viscosity increase rate was 20% or more and less than 50%. x: The viscosity increase rate was 50% or more.
  • the organic EL display element sealing material of each example and each comparative example was introduced into an inkjet cartridge DMC-11610 (manufactured by Fuji Film Dimatix).
  • the inkjet cartridge was set in an inkjet device DMP-2831 (manufactured by Fuji Film Dimatix) installed under a fluorescent light, and after adjusting the coating state, 1000 droplets were placed on a non-alkali glass of 50 mm ⁇ 50 mm at a pitch of 500 ⁇ m. applied.
  • the sealing material for an organic EL display element was left under a fluorescent lamp for 3 hours, and again, using an inkjet cartridge, 1000 droplets were applied on non-alkali glass at a pitch of 500 ⁇ m.
  • the number of droplets that could not be applied after standing for 3 hours was 98% or more of the number before standing.
  • ⁇ After standing for 3 hours, the number of droplets that could not be applied was 90% or more and less than 98% of the number before standing.
  • x After standing for 3 hours, the number of droplets that could not be applied was less than 90% of the number before standing.
  • the organic EL display element sealing material of each example and each comparative example was introduced into an inkjet cartridge DMC-11610 (manufactured by Fuji Film Dimatix). After setting the inkjet cartridge in an inkjet device DMP-2831 (manufactured by Fujifilm Dimatix) and adjusting the coating state, a 40 mm ⁇ 40 mm size was placed on a 50 mm ⁇ 50 mm alkali-free glass with a thickness of 10 ⁇ m after curing. was applied so as to be Thus, a coating film was obtained. Next, the coating film is left for 1 minute in an environment with a temperature of 25° C.
  • the coating film is irradiated with light from a UV-LED with a wavelength of 395 nm at an illuminance of 100 mW/cm 2 and 1500 mJ/cm 2 to cure. let me Thus, an evaluation board was manufactured.
  • P1a indicates the peak height of the wave number of 1371 cm after curing
  • P1b indicates the peak height of the wave number of 1371 cm -1 before curing
  • P2a indicates the peak height of the wave number of 831 cm -1 after curing .
  • Wavenumber peak height is indicated
  • P2b indicates the peak height of 831 cm ⁇ 1 wavenumber before curing.
  • the organic EL display element sealing material of each example and each comparative example was introduced into an inkjet cartridge DMC-11610 (manufactured by Fuji Film Dimatix). After setting the inkjet cartridge in an inkjet device DMP-2831 (manufactured by Fuji Film Dimatix) and adjusting the ejection state, a 15 mm ⁇ 15 mm size ink was applied to a glass substrate so that the thickness after curing was 10 ⁇ m. It was applied to obtain a coating film.
  • the coating film was left for 1 minute in an environment with a temperature of 25° C. and a humidity of 50%, and then irradiated with light from a UV-LED with a wavelength of 395 nm at an illuminance of 100 mW/cm 2 and 1500 mJ/cm 2 . , cured to obtain a cured film
  • the cured film was plasma-treated for 1 minute under the conditions of 2500 W (ICP power supply), 300 W (RF power supply), DC bias of 200 V, argon (Ar) flow rate of 50 sccm, and pressure of 10 mtorr.
  • SiNx film an inorganic sealing layer with a thickness of 100 nm was formed on the cured film side by RF sputtering using a SiNx target.
  • SiNx film an inorganic sealing layer with a thickness of 100 nm was formed on the cured film side by RF sputtering using a SiNx target.
  • an organic EL element was mounted on another glass substrate to manufacture a second evaluation substrate.
  • the first evaluation substrate and the second evaluation substrate were bonded together.
  • an evaluation organic EL display device was manufactured.
  • the organic EL display device for evaluation was subjected to a reliability test at 85°C. Specifically, the emission area ratio (%) after each organic EL display device for evaluation was stored at 85° C. for 100 hours was determined by the following method. That is, using Motic Images Plus software (manufactured by Shimadzu Rika Co., Ltd.), the luminescent area in the initial state and the luminescent area after storage for 100 hours were calculated, and the luminescent area ratio was calculated based on the following formula (8).
  • Luminescent area ratio (%) Luminous area after storage for 100 hours/Luminous area in initial state x 100 (8)
  • the reliability of the organic EL device was evaluated based on the following criteria. Table 1 shows the results. ⁇ : The emission area ratio was 80% or more. ⁇ : The emission area ratio was 50% or more and less than 80%. x: Emission area ratio was less than 50%.
  • the sealing material for an organic EL display device, the organic EL display device, and the method for manufacturing an organic EL display device of the present invention are suitably used in the manufacture of an image display device.

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Abstract

Un agent d'encapsulation pour un élément d'affichage électroluminescent organique contient un composé polymérisable par voie cationique, un initiateur de polymérisation cationique, un absorbeur d'UV et un composé ayant des groupes hydroxyle phénoliques. Le rapport en masse entre le composé ayant des groupes hydroxyle phénoliques et l'absorbeur d'UV (composé ayant des groupes hydroxyle phénoliques/absorbeur d'UV) est supérieur ou égal à 0,01 mais inférieur à 1,00.
PCT/JP2023/006769 2022-02-28 2023-02-24 Agent d'encapsulation pour élément d'affichage électroluminescent organique, dispositif d'affichage électroluminescent organique et procédé de fabrication de dispositif d'affichage électroluminescent organique WO2023163113A1 (fr)

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2003059645A (ja) * 2001-08-10 2003-02-28 Nippon Zeon Co Ltd 封止剤及びエレクトロルミネッセンス素子
JP2005306952A (ja) * 2004-04-20 2005-11-04 Japan Epoxy Resin Kk 発光素子封止材用エポキシ樹脂組成物
JP2009249569A (ja) * 2008-04-09 2009-10-29 Japan Epoxy Resin Kk 光学素子封止材用エポキシ樹脂組成物
JP2012132028A (ja) * 2012-04-09 2012-07-12 Mitsubishi Chemicals Corp 光学素子封止材用エポキシ樹脂組成物
WO2013187394A1 (fr) * 2012-06-15 2013-12-19 古河電気工業株式会社 Composition de résine d'étanchéité d'élément électroluminescent organique, pellicule d'étanchéité d'élément électroluminescent organique, pellicule de barrière contre les gaz pour élément électroluminescent organique et élément électroluminescent organique les utilisant
WO2021006070A1 (fr) * 2019-07-05 2021-01-14 三井化学株式会社 Agent d'étanchéité pour élément d'affichage électroluminescent organique, et dispositif d'affichage électroluminescent organique

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2003059645A (ja) * 2001-08-10 2003-02-28 Nippon Zeon Co Ltd 封止剤及びエレクトロルミネッセンス素子
JP2005306952A (ja) * 2004-04-20 2005-11-04 Japan Epoxy Resin Kk 発光素子封止材用エポキシ樹脂組成物
JP2009249569A (ja) * 2008-04-09 2009-10-29 Japan Epoxy Resin Kk 光学素子封止材用エポキシ樹脂組成物
JP2012132028A (ja) * 2012-04-09 2012-07-12 Mitsubishi Chemicals Corp 光学素子封止材用エポキシ樹脂組成物
WO2013187394A1 (fr) * 2012-06-15 2013-12-19 古河電気工業株式会社 Composition de résine d'étanchéité d'élément électroluminescent organique, pellicule d'étanchéité d'élément électroluminescent organique, pellicule de barrière contre les gaz pour élément électroluminescent organique et élément électroluminescent organique les utilisant
WO2021006070A1 (fr) * 2019-07-05 2021-01-14 三井化学株式会社 Agent d'étanchéité pour élément d'affichage électroluminescent organique, et dispositif d'affichage électroluminescent organique

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