WO2024095948A1 - Agent d'étanchéité, corps durci, dispositif d'affichage, procédé de production de dispositif d'affichage, cellule solaire, et composition - Google Patents

Agent d'étanchéité, corps durci, dispositif d'affichage, procédé de production de dispositif d'affichage, cellule solaire, et composition Download PDF

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Publication number
WO2024095948A1
WO2024095948A1 PCT/JP2023/039038 JP2023039038W WO2024095948A1 WO 2024095948 A1 WO2024095948 A1 WO 2024095948A1 JP 2023039038 W JP2023039038 W JP 2023039038W WO 2024095948 A1 WO2024095948 A1 WO 2024095948A1
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Prior art keywords
sealant
mass
viscosity
less
parts
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PCT/JP2023/039038
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English (en)
Japanese (ja)
Inventor
麻希子 佐々木
啓之 栗村
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デンカ株式会社
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Publication of WO2024095948A1 publication Critical patent/WO2024095948A1/fr

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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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00—Compositions of unspecified macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
    • H—ELECTRICITY
    • 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
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L33/00—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
    • H01L33/48—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof characterised by the semiconductor body packages
    • H01L33/52—Encapsulations
    • 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
    • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
    • H10K59/30—Devices specially adapted for multicolour light emission
    • H10K59/38—Devices specially adapted for multicolour light emission comprising colour filters or colour changing media [CCM]
    • 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
    • H10K85/10—Organic polymers or oligomers
    • 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

Definitions

  • the present invention relates to a sealant, a cured product, a display device, a method for manufacturing a display device, a solar cell, and a composition.
  • organic optical devices that use organic thin-film elements, such as organic electroluminescence (organic EL) display elements and organic thin-film solar cell elements.
  • organic EL organic electroluminescence
  • Organic thin-film elements are easy to fabricate using vacuum deposition, solution coating, etc., and therefore have excellent productivity.
  • An organic electroluminescent display element has a thin film structure in which an organic light-emitting material layer is sandwiched between a pair of electrodes facing each other. Electrons are injected into this organic light-emitting material layer from one electrode and holes are injected from the other electrode, whereby the electrons and holes combine in the organic light-emitting material layer to emit light by themselves.
  • Organic electroluminescent display elements have the advantages of having better visibility than liquid crystal display elements and the like that require a backlight, being able to be made thinner, and being able to be driven by a low DC voltage.
  • organic electroluminescence display elements have a problem in that when the organic light-emitting material layer or electrodes are exposed to the outside air, their light-emitting characteristics deteriorate rapidly and their lifespan is shortened. Therefore, in order to improve the stability and durability of organic electroluminescence display elements, a sealing technique that isolates the organic light-emitting material layer and electrodes from moisture and oxygen in the air is essential for organic electroluminescence display elements.
  • Examples of technologies related to sealants for organic electroluminescence elements include those described in Patent Document 1 (WO 2020/171186) and Patent Document 2 (WO 2020/067046).
  • Patent Document 1 describes a composition comprising (A) a cationic polymerizable compound, (B) a photocationic polymerization initiator, and (C) one or more phosphoric acid compounds selected from the group consisting of phosphoric esters and phosphorous esters, wherein the cationic polymerizable compound (A) comprises (A-1) an alicyclic compound having an epoxy group and (A-2) an aromatic compound having an epoxy group, the aromatic compound having an epoxy group (A-2) comprises (A-2-1) a bisphenol A type epoxy resin and (A-2-2) a bisphenol F type epoxy resin, and the ratio A 1 /A 2 (mass ratio) of the content A 1 of the bisphenol A type epoxy resin (A-2-1) to the content A 2 of the bisphenol F type epoxy resin (A-2-2) is 0.2 to 5.
  • the composition shows little increase in viscosity after irradiation with light, can be suitably used as a sealant for organic electroluminescence devices, and is unlikely to deteriorate the organic electro
  • Patent Document 2 describes a sealant for organic electroluminescence display elements that contains a cationic polymerizable compound that contains an alicyclic compound having an epoxy group and an aromatic compound having an epoxy group, a photocationic polymerization initiator, and two or more types of cure retarders selected from the group consisting of phosphoric acid-based cure retarders, ether-based cure retarders, metal complex-based cure retarders, and nitroxy radical-based cure retarders, and that the phosphoric acid-based cure retarders are selected from the group consisting of phosphoric acid esters and phosphorous esters, has a sufficiently long pot life after light irradiation, exhibits a moderate increase in viscosity after light irradiation to facilitate lamination, and has excellent reliability after curing.
  • the sealant is one that is unlikely to cause uneven application on uneven substrates such as color filters or substrates with light-emitting diode elements (TFT substrates).
  • TFT substrates light-emitting diode elements
  • the present invention has been made in consideration of the above circumstances, and provides a sealant and composition having improved coatability onto uneven substrates, as well as a display device using the sealant and a solar cell using the sealant.
  • the inventors conducted extensive research to achieve the above objective. As a result, they discovered that the coatability onto uneven substrates can be improved by setting the rate of change in viscosity before and after UV irradiation within a specific range, and thus completed the present invention.
  • the present invention provides the following sealant, cured body, display device, method for manufacturing a display device, solar cell, and composition.
  • a sealant comprising a cationic polymerizable compound (A), a cationic polymerization initiator (B), and a curing retarder (X),
  • V0 the viscosity 20 seconds after the start of measurement
  • B a cationic polymerization initiator
  • X curing retarder
  • This sealant has a viscosity change rate represented by V1 / V0 of 1.00 or more and less than 1.75.
  • V1 / V0 viscosity change rate represented by V1 / V0 of 1.00 or more and less than 1.75.
  • Apparatus Rheometer Temperature: 25°C Geometry (upper side): diameter 8 mm ⁇ , aluminum parallel plate Plate (lower side): diameter 38 mm ⁇ , non-alkali glass plate Shear rate: 1 min -1 Gap: 0.05 mm Sample amount: 20 mg
  • Atmosphere Nitrogen flow [2]
  • the content of the curing retarder (X) is 0.10 parts by mass or more and 10.0 parts by mass or less per 100 parts by mass of the cationic polymerizable compound (A).
  • the sealant according to any one of the above [1] to [15] which is for bonding a color filter to an organic electroluminescence display element or for bonding a color filter to a micro LED.
  • the sealant according to any one of the above [1] to [14] which can be used to seal a solar cell.
  • a method for manufacturing a display device comprising the steps of: [24] The method for manufacturing a display device according to [23] above, wherein one of the first member and the second member is a substrate, and the other is a light-emitting diode element. [25] The method for manufacturing a display device according to [24], wherein the light-emitting diode element includes an organic electroluminescence display element or a micro LED.
  • a solar cell comprising: a solar cell; a substrate; and a cured sealing layer between the solar cell and the substrate, the cured body being the cured body according to [19].
  • the solar cell comprises a perovskite solar cell.
  • a composition comprising a cationic polymerizable compound (A), a cationic polymerization initiator (B), and a curing retarder (X),
  • V0 the viscosity 20 seconds after the start of measurement
  • B a cationic polymerization initiator
  • X curing retarder
  • the viscosity change rate represented by V1 / V0 is 1.00 or more and less than 1.75.
  • the present invention provides a sealant and composition with improved coatability on uneven substrates, as well as a display device using the sealant and a solar cell using the sealant.
  • the sealant of the present embodiment is a sealant containing a cationic polymerizable compound (A), a cationic polymerization initiator (B), and a cure retarder (X), and in a viscosity measurement under the following measurement condition 1, when the viscosity 20 seconds after the start of the measurement is defined as V0 , and 30 seconds after the start of the measurement, the non-alkali glass plate is irradiated with ultraviolet light having a wavelength of 365 nm and 30 mW/ cm2 perpendicularly toward the non-alkali glass plate from a point 15 cm away from the non-alkali glass plate for 20 seconds (total 600 mJ/ cm2 ), and the viscosity 60 seconds after the completion of the ultraviolet light irradiation is defined as V1 , the viscosity change rate represented by V1 / V0 is 1.00 or more and less than 1.75.
  • V1 cationic polymerizable compound
  • B cationic polymerization initiator
  • the sealant of this embodiment since the viscosity change rate represented by V1 / V0 is within the above range, it is possible to improve the applicability to an uneven substrate such as a color filter or a substrate with a light-emitting diode element (TFT substrate). Since the sealant of this embodiment easily spreads evenly on an uneven substrate, it is possible to suppress the remaining air bubbles in the coating film, and as a result, it is possible to form a cured sealing layer with improved transparency on the uneven substrate.
  • an uneven substrate such as a color filter or a substrate with a light-emitting diode element (TFT substrate). Since the sealant of this embodiment easily spreads evenly on an uneven substrate, it is possible to suppress the remaining air bubbles in the coating film, and as a result, it is possible to form a cured sealing layer with improved transparency on the uneven substrate.
  • TFT substrate light-emitting diode element
  • the sealant of this embodiment is controlled so that the viscosity change rate represented by the above V1 / V0 is 1.00 or more and less than 1.75. This improves the applicability of the sealant of this embodiment to a substrate having projections and recesses. The reason for this is not clear, but the following reasons are thought to be the cause. First, it is believed that by having the viscosity change rate represented by the above V1 / V0 be equal to or higher than the lower limit, it is possible to prevent the coated droplets from excessively spreading and becoming non-uniform in thickness.
  • the coating film can be easily spread over the uneven surface of the substrate, thereby preventing air bubbles from remaining in the coating film and non-uniform thickness.
  • the sealant of this embodiment has a viscosity change rate, represented by V1 / V0 , of 1.00 or more and less than 1.75. From the viewpoint of further improving the coatability to uneven substrates, the viscosity change rate is preferably 1.74 or less, more preferably 1.73 or less, even more preferably 1.70 or less, even more preferably 1.65 or less, and even more preferably 1.60 or less.
  • the viscosity V0 of the sealant of this embodiment is preferably 1 mPa ⁇ s or more, more preferably 10 mPa ⁇ s or more, even more preferably 50 mPa ⁇ s or more, even more preferably 70 mPa ⁇ s or more, even more preferably 100 mPa ⁇ s or more, even more preferably 150 mPa ⁇ s or more, and is preferably 1000 mPa ⁇ s or less, more preferably 800 mPa ⁇ s or less, even more preferably 500 mPa ⁇ s or less, even more preferably 300 mPa ⁇ s or less, and even more preferably 250 mPa ⁇ s or less.
  • the viscosity V1 of the sealant of this embodiment is preferably 1 mPa ⁇ s or more, more preferably 10 mPa ⁇ s or more, even more preferably 50 mPa ⁇ s or more, even more preferably 70 mPa ⁇ s or more, even more preferably 100 mPa ⁇ s or more, and even more preferably 150 mPa ⁇ s or more, and is preferably 2000 mPa ⁇ s or less, more preferably 1500 mPa ⁇ s or less, even more preferably 1000 mPa ⁇ s or less, even more preferably 800 mPa ⁇ s or less, even more preferably 600 mPa ⁇ s or less, and even more preferably 500 mPa ⁇ s or less.
  • the viscosity V2 10 minutes after the completion of the ultraviolet irradiation is, from the viewpoint of further improving the performance balance of the coatability to a rough substrate and the dischargeability during coating in the sealant of this embodiment, and from the viewpoint of obtaining a longer pot life, preferably 10 mPa ⁇ s or more, more preferably 20 mPa ⁇ s or more, even more preferably 100 mPa ⁇ s or more, even more preferably 150 mPa ⁇ s or more, even more preferably 200 mPa ⁇ s or more, even more preferably 300 mPa ⁇ s or more, and preferably 5000 mPa ⁇ s or less, more preferably 4000 mPa ⁇ s or less, even more preferably 3000 mPa ⁇ s or less, even more preferably 2000 mPa ⁇ s or less, even more preferably 1800 mPa ⁇ s or less, even more preferably 1500 mPa ⁇ s or less, even more preferably 1200 mPa
  • the sealant of this embodiment has good coatability on uneven substrates, and can therefore be suitably used as a sealant for light-emitting diode elements, and can be more suitably used as a sealant for organic electroluminescent display elements, and can be even more suitably used for bonding a color filter to an organic electroluminescent display element or a color filter to a micro LED.
  • the sealant of this embodiment can preferably be used to seal a solar cell.
  • the solar cell of this embodiment is preferably a perovskite solar cell.
  • the (A) component is a compound having cationic polymerizability, and can also be called a compound having a cationic polymerizable group.
  • the cationic polymerizable group include cyclic ether groups such as an epoxy group (oxirane ring) and an oxetane group (oxetane ring); and cationic polymerizable vinyl groups.
  • the (A) component preferably contains an epoxy group.
  • the (A) component is preferably photopolymerizable.
  • the component (A) preferably contains one or more compounds selected from the group consisting of an epoxy compound, an oxetane compound, and a cationically polymerizable vinyl compound, and more preferably contains an epoxy compound.
  • the epoxy compound include an alicyclic compound having an epoxy group (A-1) (alicyclic epoxy compound), an aromatic compound having an epoxy group (A-2) (aromatic epoxy compound), and a glycidyl ether compound (A-3).
  • Component (A) may be a compound having one cationic polymerizable group, or may be a compound having two or more cationic polymerizable groups.
  • Component (A) preferably has two or more cationic polymerizable groups, and more preferably has two cationic polymerizable groups.
  • the component (A) preferably contains one or more compounds selected from the group consisting of an alicyclic compound having an epoxy group (A-1), an aromatic compound having an epoxy group (A-2), and a glycidyl ether compound (A-3), and more preferably contains an alicyclic compound having an epoxy group (A-1), an aromatic compound having an epoxy group (A-2), and a glycidyl ether compound (A-3).
  • the component (A) preferably contains a bromine atom.
  • the component (A) containing a bromine atom means that the component (A) contains a bromine atom-containing compound.
  • the (A1) component is a compound having an epoxy group and an alicyclic group.
  • the (A1) component may be a compound having one epoxy group, or may be a compound having two or more epoxy groups.
  • the (A1) component preferably has two or more epoxy groups, and more preferably has two epoxy groups.
  • the (A1) component may be a compound having no aromatic ring.
  • the (A1) component may be used alone or in combination of two or more.
  • the component (A1) may be, for example, a compound obtained by epoxidizing a compound having a cycloalkene ring, or a derivative thereof.
  • the cycloalkene ring include a cyclohexene ring, a cyclopentene ring, and a pinene ring.
  • the epoxidation can be carried out, for example, using an oxidizing agent.
  • the oxidizing agent include hydrogen peroxide and peracid.
  • Such component (A1) include one or more selected from the group consisting of 3',4'-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, 3,4-epoxycyclohexylalkyl(meth)acrylate (e.g., 3,4-epoxycyclohexylmethyl(meth)acrylate), and (3,3',4,4'-diepoxy)bicyclohexyl.
  • the (A1) component may be, for example, a compound obtained by hydrogenating a compound having an epoxy group and an aromatic ring, or a derivative thereof.
  • compounds having an epoxy group and an aromatic ring include bisphenol A type epoxy resins and bisphenol F type epoxy resins.
  • Examples of such (A-1) components include hydrogenated bisphenol A type epoxy resins and hydrogenated bisphenol F type epoxy resins.
  • component (A1) a compound having a 1,2-epoxycyclohexane structure is preferred.
  • a compound having a 1,2-epoxycyclohexane structure for example, a compound represented by formula (A1-1) is preferred.
  • X represents a single bond or a linking group (a divalent group having one or more atoms).
  • the compound represented by formula (A1-1) is (3,3',4,4'-diepoxy)bicyclohexyl.
  • the linking group may be, for example, a divalent hydrocarbon group, a carbonyl group, an ether bond, an ester bond, a carbonate group, an amide bond, or a group in which a plurality of these are linked together.
  • X is preferably a linking group.
  • the linking group is preferably a group having an ester bond, and more preferably a group in which an ester bond and a divalent hydrocarbon group are linked together.
  • An example of a compound having a group having an ester bond as a linking group is 3',4'-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate (molecular weight 252).
  • the divalent hydrocarbon group is preferably an alkanediyl group, more preferably an alkanediyl group having 1 to 3 carbon atoms.
  • the compound represented by formula (A1-1) is preferably 3',4'-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate.
  • the molecular weight of component (A1) is preferably 450 or less, more preferably 400 or less, even more preferably 300 or less, and even more preferably 280 or less, from the viewpoint of further improving the balance of performance among the coatability of the sealant to a rough substrate, the storage stability of the sealant, and the moisture resistance of the cured product.
  • the molecular weight of component (A1) may be, for example, 100 or more, 150 or more, or 200 or more.
  • the number average molecular weight of the component (A1) is preferably in the above-mentioned range.
  • the number average molecular weight refers to a value calculated in terms of polystyrene measured by gel permeation chromatography (GPC) under the following measurement conditions.
  • the (A2) component is a compound having an epoxy group and an aromatic ring.
  • the (A2) component may be a compound having one epoxy group, or may be a compound having two or more epoxy groups.
  • the (A2) component preferably has two or more epoxy groups, and more preferably has two epoxy groups.
  • the (A2) component may be a compound not having an alicyclic group.
  • the (A2) component may be used alone or in combination of two or more.
  • any of a monomer, oligomer, or polymer can be used, and examples thereof include one or more selected from the group consisting of bisphenol A type epoxy resins, bisphenol F type epoxy resins, bisphenol S type epoxy resins, biphenyl type epoxy resins, naphthalene type epoxy resins, fluorene type epoxy resins, novolac phenol type epoxy resins, cresol novolac type epoxy resins, and modified products thereof.
  • halophenyl glycidyl ethers such as bromophenyl glycidyl ether and dibromophenyl glycidyl ether
  • bromine atom-containing epoxy resins such as brominated bisphenol A type epoxy resins, brominated bisphenol F type novolac type epoxy resins, and brominated phenol novolac type epoxy resins
  • other bromine atom-containing aromatic epoxy compounds As the bromine atom-containing aromatic epoxy compound, halophenyl glycidyl ether is preferred.
  • dibromophenyl glycidyl ether is preferred.
  • the (A2) component preferably contains one or more compounds selected from the group consisting of compounds having a bisphenol structure (e.g., bisphenol A structure, bisphenol F structure, bisphenol S structure, etc.) and bromine atom-containing aromatic epoxy compounds, more preferably contains one or more compounds selected from the group consisting of bisphenol A type epoxy resins, bisphenol F type epoxy resins, and halophenyl glycidyl ethers, even more preferably contains one or more compounds selected from the group consisting of bisphenol A type epoxy resins, bisphenol F type epoxy resins, and dibromophenyl glycidyl ethers, and even more preferably contains at least one compound selected from the group consisting of bisphenol F type epoxy resins and dibromophenyl glycidyl ethers.
  • a bisphenol structure e.g., bisphenol A structure, bisphenol F structure, bisphenol S structure, etc.
  • bromine atom-containing aromatic epoxy compounds more preferably contains one or more compounds selected from the group
  • the molecular weight of component (A2) is preferably 100 or more, more preferably 150 or more, and even more preferably 200 or more, from the viewpoint of further improving the balance of performance among the coatability of the sealant to a rough substrate, the storage stability of the sealant, and the moisture resistance of the cured product, and is preferably 5000 or less, more preferably 1000 or less, and even more preferably 450 or less.
  • the number average molecular weight of component (A2) is within the above range.
  • the number average molecular weight refers to a polystyrene-equivalent value measured by gel permeation chromatography (GPC) under the above-mentioned measurement conditions.
  • the (A3) component is a compound having a glycidyl ether group.
  • the (A3) component may be a compound having one epoxy group, or may be a compound having two or more epoxy groups.
  • the (A3) component preferably has two or more epoxy groups, and more preferably has two epoxy groups.
  • the (A3) component may be a compound having no alicyclic group or aromatic ring.
  • the (A3) component may be used alone or in combination of two or more.
  • the (A3) component is preferably excluding the (A1) and (A2) components.
  • the component (A3) is preferably a diglycidyl ether compound.
  • the diglycidyl ether compound preferably includes one or more compounds selected from the group consisting of diglycidyl ethers of alkylene glycols, such as diglycidyl ether of ethylene glycol, diglycidyl ether of propylene glycol, diglycidyl ether of 1,6-hexanediol, and diglycidyl ether of neopentyl glycol; polyglycidyl ethers of polyhydric alcohols, such as di- or triglycidyl ethers of glycerin or an alkylene oxide adduct thereof; and diglycidyl ethers of polyalkylene glycols, such as diglycidyl ethers of polyethylene glycol or an alkylene oxide adduct thereof, and diglycidyl ethers of polypropylene glycol
  • the diglycidyl ether of alkylene glycol preferably includes one or more selected from the group consisting of diglycidyl ether of ethylene glycol, diglycidyl ether of propylene glycol, diglycidyl ether of 1,6-hexanediol, and diglycidyl ether of neopentyl glycol, and more preferably includes one or two selected from the group consisting of diglycidyl ether of 1,6-hexanediol and diglycidyl ether of neopentyl glycol.
  • the alkylene glycol include ethylene glycol, propylene glycol, 1,6-hexanediol, neopentyl glycol, etc.
  • the polyalkylene glycol include polyethylene glycol or its alkylene oxide adduct, polypropylene glycol or its alkylene oxide adduct, etc.
  • the alkylene oxide include ethylene oxide, propylene oxide, etc.
  • the content of the (A1) component in the sealant of this embodiment when the total amount of the (A) component in the sealant of this embodiment is taken as 100 parts by mass, is preferably 10.0 parts by mass or more, more preferably 15.0 parts by mass or more, even more preferably 18.0 parts by mass or more, even more preferably 30.0 parts by mass or more, even more preferably 40.0 parts by mass or more, even more preferably 50.0 parts by mass or more, even more preferably 55.0 parts by mass or more, even more preferably 60.0 parts by mass or more, and is preferably 90.0 parts by mass or less, more preferably 85.0 parts by mass or less, even more preferably 80.0 parts by mass or less, even more preferably 75.0 parts by mass or less.
  • the content of the (A2) component in the sealant of this embodiment when the total amount of the (A) component in the sealant of this embodiment is taken as 100 parts by mass, is preferably 5.0 parts by mass or more, more preferably 10.0 parts by mass or more, even more preferably 15.0 parts by mass or more, even more preferably 20.0 parts by mass or more, even more preferably 25.0 parts by mass or more, and is preferably 65.0 parts by mass or less, more preferably 60.0 parts by mass or less, even more preferably 55.0 parts by mass or less, even more preferably 50.0 parts by mass or less, even more preferably 45.0 parts by mass or less.
  • the content of the (A3) component in the sealant of this embodiment when the total amount of the (A) component in the sealant of this embodiment is taken as 100 parts by mass, is preferably 0.1 parts by mass or more, more preferably 0.2 parts by mass or more, even more preferably 0.5 parts by mass or more, even more preferably 1.0 parts by mass or more, even more preferably 1.5 parts by mass or more, and is preferably 90.0 parts by mass or less, more preferably 85.0 parts by mass or less, even more preferably 82.0 parts by mass or less, even more preferably 20.0 parts by mass or less, even more preferably 15.0 parts by mass or less, even more preferably 10.0 parts by mass or less, even more preferably 5.0 parts by mass or less, even more preferably 3.0 parts by mass or less.
  • the total content of the (A1), (A2) and (A3) components in the sealant of this embodiment is preferably 60 parts by mass or more, more preferably 70 parts by mass or more, even more preferably 80 parts by mass or more, even more preferably 95 parts by mass or more, even more preferably 98 parts by mass or more, and may be 100 parts by mass.
  • the component (B) can be one or more selected from the group consisting of a photocationic polymerization initiator that can be activated by light to initiate cationic polymerization of the component (A); and a thermal cationic polymerization initiator that can be activated by heat to initiate cationic polymerization of the component (A).
  • a photocationic polymerization initiator is preferred.
  • arylsulfonium salt derivatives e.g., Cyracure UVI-6990 and Cyracure UVI-6974 manufactured by Dow Chemical Company, Adeka Optomer SP-150, Adeka Optomer SP-152, Adeka Optomer SP-170, and Adeka Optomer SP-172 manufactured by ADEKA Corporation, CPI-100P, CPI-101A, and CPI-20 manufactured by San-Apro Co., Ltd.) 0K, CPI-210S, CPI-310FG, LW-S1, CibaCure-1190 manufactured by Double Bond, etc.), aryl iodonium salt derivatives (e.g.,
  • thermal cationic polymerization initiator examples include any thermal cationic polymerization initiator that is activated by heating to induce ring-opening of a ring-opening polymerizable group, etc.
  • thermal cationic polymerization initiator examples include onium salt compounds such as quaternary ammonium salts, phosphonium salts, and sulfonium salts, etc.
  • thermal cationic polymerization initiators include, for example, ADEKAOPTON CP-66, ADEKAOPTON CP-77 (manufactured by ADEKA CORPORATION), SAN-AID SI-60L, SAN-AID SI-80L, SAN-AID SI-100L (manufactured by Sanshin Chemical Industry Co., Ltd.), and CI series (manufactured by Nippon Soda Co., Ltd.).
  • the component (B) preferably contains an onium salt compound, from the viewpoint that the above-mentioned effect can be more significantly obtained by using two or more types of cure retarders.
  • the onium salt compound preferably contains one or more types selected from the group consisting of arylsulfonium salt derivatives, aryl iodonium salt derivatives, and diazonium salt derivatives, and more preferably contains an arylsulfonium salt derivative.
  • the anion preferably contains one or more types selected from the group consisting of antimonate and gallate.
  • Component (B) may be dissolved in a solvent in advance to facilitate mixing with other components such as component (A).
  • the solvent is not particularly limited, but examples include carbonates such as propylene carbonate, ethylene carbonate, 1,2-butylene carbonate, dimethyl carbonate, and diethyl carbonate.
  • the content of component (B) in the sealant of this embodiment is, from the viewpoint of further improving the curing property of the sealant, preferably 0.01 parts by mass or more, more preferably 0.05 parts by mass or more, even more preferably 0.10 parts by mass or more, even more preferably 0.15 parts by mass or more, and even more preferably 0.20 parts by mass or more, relative to 100 parts by mass of component (A), and from the viewpoint of further improving the adhesive durability of the cured product, is preferably 5.0 parts by mass or less, more preferably 3.0 parts by mass or less, even more preferably 2.0 parts by mass or less, even more preferably 1.0 parts by mass or less, even more preferably 0.70 parts by mass or less, even more preferably 0.50 parts by mass or less, and even more preferably 0.30 parts by mass or less.
  • the sealant of the present embodiment contains a curing retarder as the component (X).
  • the component (X) preferably contains one or more types selected from the group consisting of a phosphoric acid-based cure retarder (component (C)), an ether-based cure retarder (component (D)), a thioether-based cure retarder (component (E)), a metal complex-based cure retarder (component (F)) and a nitroxy radical-based cure retarder (component (G)), and more preferably contains one or more types selected from the group consisting of a phosphoric acid-based cure retarder (component (C)) and an ether-based cure retarder (component (D)).
  • the content of the (X) component in the sealant of this embodiment is preferably 0.10 parts by mass or more, more preferably 0.20 parts by mass or more, even more preferably 0.50 parts by mass or more, even more preferably 0.80 parts by mass or more, and even more preferably 1.0 parts by mass or more, per 100 parts by mass of the (A) component, from the viewpoint of obtaining a longer pot life, and is preferably 10.0 parts by mass or less, more preferably 5.0 parts by mass or less, even more preferably 2.0 parts by mass or less, and even more preferably 1.5 parts by mass or less, from the viewpoint of further improving the performance balance of the moisture resistance and adhesiveness of the cured body.
  • the phosphoric acid-based hardening retarder is a hardening retarder selected from the group consisting of a phosphoric acid ester (component (C1)) and a phosphorous acid ester (component (C2)).
  • the component (C) can be used alone or in combination of two or more kinds.
  • the (C1) component preferably contains one or more compounds selected from the group consisting of compounds represented by formula (C1-1), compounds represented by formula (C1-2), and compounds represented by formula (C1-3), and more preferably contains a compound represented by formula (C1-2).
  • R 1 , R 2 , R 3 , R 4 , R 5 and R 6 each independently represent a hydrocarbon group which may have a substituent.
  • R 2 , R 3 and R 4 in formula (C1-2), and R 5 and R 6 in formula (C1-3) are the same groups in each formula.
  • Examples of the substituent that the hydrocarbon group in R 1 , R 2 , R 3 , R 4 , R 5 and R 6 may have include an oxyalkyl group, etc.
  • the hydrocarbon group in R 1 , R 2 , R 3 , R 4 , R 5 and R 6 is preferably an unsubstituted hydrocarbon group.
  • the hydrocarbon group in R 1 , R 2 , R 3 , R 4 , R 5 and R 6 is preferably an alkyl group or an aryl group, more preferably an alkyl group or a phenyl group, and further preferably an alkyl group.
  • the number of carbon atoms in the alkyl group may be, for example, 1 to 18, and preferably 4 to 13.
  • the compound represented by formula (C1-1) may be, for example, a monoalkyl phosphate (i.e., a compound in which R 1 is an alkyl group), and specific examples thereof include monoethyl phosphate, mono-n-butyl phosphate, mono(butoxyethyl)phosphate, and mono(2-ethylhexyl)phosphate.
  • a monoalkyl phosphate i.e., a compound in which R 1 is an alkyl group
  • specific examples thereof include monoethyl phosphate, mono-n-butyl phosphate, mono(butoxyethyl)phosphate, and mono(2-ethylhexyl)phosphate.
  • the compound represented by formula (C1-2) is preferably a trialkyl phosphate (i.e., a compound in which R 2 , R 3 and R 4 are alkyl groups).
  • the number of carbon atoms in the alkyl groups of R 2 , R 3 and R 4 is preferably 1 or more and 18 or less, more preferably 4 or more and 12 or less, and even more preferably 8.
  • trialkyl phosphates include triethyl phosphate, tri-n-butyl phosphate, tris(butoxyethyl) phosphate, tris(2-ethylhexyl) phosphate, (RO) 3 P ⁇ O (R is a lauryl group, a cetyl group, a stearyl group, or an oleyl group), and the like.
  • Examples of the compound represented by formula (C1-3) include dialkyl phosphates (i.e., compounds in which R5 and R6 are alkyl groups), etc.
  • Specific examples of dialkyl phosphates include dibutyl phosphate, bis(2-ethylhexyl) phosphate, etc.
  • the (C2) component is a phosphorous ester.
  • Examples of the (C2) component include trimethyl phosphite, triethyl phosphite, tri-n-butyl phosphite, tris(2-ethylhexyl) phosphite, triisooctyl phosphite, tridecyl phosphite, triisodecyl phosphite, tris(tridecyl) phosphite, trioleyl phosphite, tristearyl phosphite, triphenyl phosphite, tris(nonylphenyl) phosphite, tris(2,4-di-t-butylphenyl) phosphite, phenyl diisooctyl phosphite, phenyl diisodecyl phosphite, diphenyl mono(2-
  • the (C2) component preferably contains one or more compounds selected from the group consisting of compounds represented by formula (C2-1), compounds represented by formula (C2-2), compounds represented by formula (C2-3), compounds represented by formula (C2-4), compounds represented by formula (C2-5), and compounds represented by formula (C2-6).
  • R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17 each independently represent a hydrocarbon group which may have a substituent.
  • Examples of the substituent that the hydrocarbon group in R7 , R8 , R9, R10 , R11 , R12 , R13 , R14 , R15 , R16 , and R17 may have include an oxyalkyl group, etc.
  • the hydrocarbon group in R7 , R8 , R9, R10 , R11 , R12 , R13 , R14 , R15 , R16 , and R17 is preferably an unsubstituted hydrocarbon group.
  • the hydrocarbon group in R7 , R8 , R9, R10 , R11 , R12 , R13 , R14 , R15 , R16 and R17 is preferably an alkyl group or an aryl group, more preferably an alkyl group or a phenyl group, and even more preferably an alkyl group.
  • the number of carbon atoms in the alkyl group may be, for example, 1 to 30, preferably 1 to 18.
  • the aryl group is preferably a phenyl group.
  • R 8 and R 9 in formula (C2-2), R 10 , R 11 and R 12 in formula (C2-3), R 13 and R 14 in formula (C2-4), and R 15 and R 16 in formula (C2-5) are the same as each other in each formula.
  • Examples of the compound represented by formula (C2-1) include monoalkyl phosphites (that is, compounds in which R 7 is an alkyl group).
  • Examples of the compound represented by formula (C2-2) include dialkyl phosphites (that is, compounds in which R 8 and R 9 are alkyl groups).
  • Examples of the compound represented by formula (C2-3) include trialkyl phosphites (i.e., compounds in which R 10 , R 11 and R 12 are alkyl groups), phenyl phosphites (i.e., compounds in which one or more of R 10 , R 11 and R 12 are phenyl groups), etc.
  • Specific examples of trialkyl phosphites include triethyl phosphite, tris(2-ethylhexyl)phosphite, tridecyl phosphite, trilauryl phosphite, tris(tridecyl)phosphite, trioleyl phosphite, etc.
  • Specific examples of phenyl phosphites include diphenyl monodecyl phosphite, etc.
  • Examples of the compound represented by formula (C2-4) include bis(alkyl)pentaerythritol diphosphites (i.e., compounds in which R 13 and R 14 are alkyl groups), etc.
  • Specific examples of the compound represented by formula (C2-4) include bis(decyl)pentaerythritol diphosphite, bis(tridecyl)pentaerythritol diphosphite, distearyl pentaerythritol diphosphite, etc.
  • Examples of the compound represented by formula (C2-5) include dialkyl hydrogen phosphite (i.e., a compound in which R 15 and R 16 are alkyl groups), etc.
  • Specific examples of the compound represented by formula (C2-5) include diethyl hydrogen phosphite, bis(2-ethylhexyl) hydrogen phosphite, dilauryl hydrogen phosphite, dioleyl hydrogen phosphite, etc.
  • Examples of the compound represented by formula (C2-6) include monoalkyl hydrogen phosphites (i.e., compounds in which R 17 is an alkyl group), etc. Specific examples of the compound represented by formula (C2-6) include monoethyl hydrogen phosphite, mono(2-ethylhexyl) hydrogen phosphite, monolauryl hydrogen phosphite, monooleyl hydrogen phosphite, etc.
  • C2 components include trimethyl phosphite, triethyl phosphite, tri-n-butyl phosphite, tris(2-ethylhexyl) phosphite, triisooctyl phosphite, tridecyl phosphite, triisodecyl phosphite, tris(tridecyl) phosphite, trioleyl phosphite, tristearyl phosphite, triphenyl phosphite, tris(nonylphenyl) phosphite, diisodecyl pentaerythritol diphosphite, bis(tridecyl)pentaerythritol diphosphite, distearyl pentaerythritol diphosphite, bis(nonylphenyl)pentaerythritol diphosphite,
  • the content of the (C) component in the sealant of this embodiment is, from the viewpoint of obtaining a longer pot life, preferably 0.001 parts by mass or more, more preferably 0.005 parts by mass or more, even more preferably 0.01 parts by mass or more, even more preferably 0.02 parts by mass or more, even more preferably 0.05 parts by mass or more, even more preferably 0.10 parts by mass or more, and even more preferably 0.20 parts by mass or more, per 100 parts by mass of the (A) component; and from the viewpoint of further improving the performance balance of the moisture resistance and adhesiveness of the cured product, it is preferably 5.0 parts by mass or less, more preferably 2.0 parts by mass or less, even more preferably 1.0 parts by mass or less, and even more preferably 0.5 parts by mass or less.
  • the component (D) is a cure retarder having an ether bond.
  • the component (D) may be used alone or in combination of two or more.
  • the (D) component may be a linear ether or a cyclic ether.
  • linear ethers include polyalkylene oxides such as polyethylene glycol, polypropylene glycol, and polyoxytetramethylene glycol.
  • polyalkylene oxides include polyoxyethylene-dimethyl ether.
  • cyclic ethers include crown ethers. Examples of crown ethers include 18-crown-6-ether and 15-crown-5-ether.
  • component (D) is preferably a cyclic ether, more preferably a crown ether, and even more preferably 18-crown-6-ether.
  • the content of the (D) component in the sealant of this embodiment is preferably 0.01 parts by mass or more, more preferably 0.02 parts by mass or more, even more preferably 0.05 parts by mass or more, even more preferably 0.10 parts by mass or more, even more preferably 0.20 parts by mass or more, and even more preferably 0.50 parts by mass or more, per 100 parts by mass of the (A) component, from the viewpoint of obtaining a longer pot life, and is preferably 10.0 parts by mass or less, more preferably 5.0 parts by mass or less, even more preferably 3.0 parts by mass or less, even more preferably 2.0 parts by mass or less, and even more preferably 1.5 parts by mass or less, from the viewpoint of further improving the performance balance of the moisture resistance and adhesiveness of the cured product.
  • Component (E) Thioether-based cure retarder>
  • the component (E) is a cure retarder having a thioether bond.
  • the component (E) may be used alone or in combination of two or more.
  • the (E) component may be a chain thioether or a cyclic thioether.
  • chain thioethers include diethyl thioether, isobutyl sulfide, and dithiaoctanediol.
  • cyclic thioethers include 1,3-dithiane, 1,3,5-trithiane, 1,4,7-trithiacyclononane, and 1,4,8,11-tetrathiacyclotetradecane.
  • the component (F) may be any metal complex that functions as a cure retarder.
  • Examples of the component (F) include metal acetylacetonates.
  • the component (F) may be used alone or in combination of two or more.
  • metal acetylacetonates include acetylacetonates of aluminum, titanium, zinc, zirconium, and copper. Among these, acetylacetonates of aluminum and zinc are preferred, and aluminum acetylacetonate is more preferred.
  • the content of the (F) component in the sealant of this embodiment is preferably 0.01 parts by mass or more, more preferably 0.02 parts by mass or more, per 100 parts by mass of the (A) component, from the viewpoint of obtaining a longer pot life, and is preferably 2.0 parts by mass or less, more preferably 1.0 part by mass or less, from the viewpoint of further improving the performance balance of the moisture resistance and adhesiveness of the cured product.
  • the component (G) is a cure retarder having a nitroxide group.
  • the component (G) may be used alone or in combination of two or more.
  • (G) component includes, for example, 2,2,6,6-tetramethyl-1-piperidinyloxy (hereinafter referred to as TEMPO) or its derivatives such as 4-benzooxyloxy-TEMPO, 4-methoxy-TEMPO, 4-carboxyl-4-amino-TEMPO, 4-chloro-TEMPO, 4-hydroxylimine-TEMPO, 4-hydroxy-TEMPO, 4-oxo-TEMPO, etc.; 4-amino-TEMPO, 2,2,5,5-tetramethyl-1-pyrrolidinyloxy (hereinafter referred to as PROXYL) or its derivatives such as 3-carboxyl-PROXYL, 3-carbamoyl-PROXYL, 2,2-dimethyl-4,5-cyclohexyl-PROXYL, 3-oxo-PROXYL, 3-hydroxylimine- PROXYL, 3-aminomethyl-PROXYL, 3-methoxy-PROXYL, 3-t-butyl-PROXYL, 3-maleimi
  • the preferred component (G) is 2,2,6,6-tetramethyl-1-piperidinyloxy.
  • the content of the (G) component in the sealant of this embodiment is preferably 0.01 parts by mass or more, more preferably 0.02 parts by mass or more, per 100 parts by mass of the (A) component, from the viewpoint of obtaining a longer pot life, and is preferably 2.0 parts by mass or less, more preferably 1.0 part by mass or less, from the viewpoint of further improving the performance balance of the moisture resistance and adhesiveness of the cured product.
  • the sealant of the present embodiment preferably contains the (C) component and the (D) component as the (X) component.
  • the mass ratio (C 1 /D 1 ) of the content C 1 of the (C) component to the content D 1 of the (D) component is preferably 0.001 or more, more preferably 0.005 or more, even more preferably 0.01 or more, even more preferably 0.05 or more, even more preferably 0.10 or more, and even more preferably 0.20 or more from the viewpoint of further improving the applicability of the sealant to the uneven substrate, and is preferably 2.0 or less, more preferably 1.0 or less, and even more preferably 0.5 or less from the viewpoint of further improving the moisture resistance and adhesion of the cured body.
  • the total content of the (A), (B) and (X) components in the sealant of this embodiment is preferably 60% by mass or more, more preferably 70% by mass or more, even more preferably 80% by mass or more, even more preferably 90% by mass or more, even more preferably 95% by mass or more, even more preferably 98% by mass or more, and may be 100% by mass or less, from the viewpoint of further improving the coatability to uneven substrates.
  • the sealant of the present embodiment may further contain other components in addition to the component (A), the component (B), and the component (X).
  • ingredients include, for example, photosensitizers, silane coupling agents, antioxidants, inorganic fillers, resin particles, metal deactivators, bulking agents, stabilizers, neutralizing agents, lubricants, and antibacterial agents.
  • the method for producing the sealant of this embodiment is not particularly limited as long as the above components can be mixed sufficiently.
  • the method for mixing the components is not particularly limited, but examples include a mixing method that uses the mixing force caused by the rotation of a propeller, and a method that uses a normal dispersing machine such as a planetary mixer that rotates and revolves around its axis. These mixing methods are preferred because they are low cost and allow stable mixing.
  • the sealant can be applied to an object (e.g., a member constituting a display device) and cured on the object to form a hardened sealing layer made of the hardened sealant.
  • an object e.g., a member constituting a display device
  • the sealant of this embodiment may also be cured into a predetermined shape (e.g., a film, a sheet, etc.) to form a cured sealing layer having a predetermined shape.
  • a predetermined shape e.g., a film, a sheet, etc.
  • the cured sealing layer can be placed on a light-emitting diode element to seal the light-emitting diode element.
  • the hardened sealing layer may be made of a hardened sealant, or may contain a hardened sealant and other constituent materials.
  • other constituent materials include inorganic layers such as silicon nitride films, silicon oxide films, and silicon oxynitride, as well as inorganic fillers such as silica, mica, kaolin, talc, and aluminum oxide.
  • the sealant of this embodiment makes it easy to manufacture a display device that includes a light-emitting diode element and a cured sealant layer.
  • the liquid density of the sealant of this embodiment in an atmosphere of 25°C is preferably 1.10 or more, more preferably 1.12 or more, even more preferably 1.15 or more, even more preferably 1.20 or more, and is preferably 4.0 or less, more preferably 3.0 or less, even more preferably 2.5 or less, even more preferably 2.0 or less, even more preferably 1.5 or less, from the viewpoint of further improving the applicability of the sealant to uneven substrates.
  • the liquid density of the sealant of this embodiment is a value measured using a 5 mL Gay-Lussac type pycnometer in accordance with 8.2.2 of JIS-K-0061. The type and content of each component of the sealant of this embodiment may be appropriately adjusted so that the liquid density falls within the above range.
  • the static surface tension of the sealant of this embodiment is preferably 50 mN/m or less, more preferably 40 mN/m or less, and even more preferably 35 mN/m or less, from the viewpoint of further improving the applicability of the sealant to uneven substrates.
  • the lower limit of the static surface tension is not particularly limited, but may be, for example, 10 mN/m or more, 20 mN/m or more, or 25 mN/m or more.
  • the pendant drop method is a method in which liquid is pushed out from the tip of a tube and the surface tension is calculated from the shape of the pendant drop that hangs down.
  • the cured product of the present embodiment is obtained by curing the sealant of the present embodiment. That is, by curing the sealant of the present embodiment, a cured body containing a polymer of the cationically polymerizable compound (A) can be obtained.
  • the cured body of the present embodiment can be suitably used as a cured sealing layer (particularly, a cured sealing layer for a light-emitting diode element).
  • the sealant of this embodiment for example, increases in viscosity moderately after light irradiation, and then hardens as the polymerization reaction of the cationic polymerizable compound (A) progresses. After light irradiation, the sealant can also be rapidly hardened by heating.
  • the light source for irradiating the sealant of this embodiment is not particularly limited, and examples include halogen lamps, metal halide lamps, high-power metal halide lamps (containing indium, etc.), low-pressure mercury lamps, high-pressure mercury lamps, ultra-high-pressure mercury lamps, xenon lamps, xenon excimer lamps, xenon flash lamps, LEDs, etc. These light sources are preferred in that they can efficiently irradiate energy rays that correspond to the reaction wavelength of the photocationic polymerization initiator.
  • the above light sources each have different emission wavelengths and energy distributions. Therefore, the above light source can be appropriately selected based on the reaction wavelength of the photocationic polymerization initiator. Natural light (sunlight) can also be a light source that starts the reaction of the sealant.
  • the irradiation method may be direct irradiation, focused irradiation using a reflector, or focused irradiation using a fiber. Irradiation may also be performed using a low wavelength cut filter, a heat ray cut filter, a cold mirror, etc.
  • the amount of light irradiation is not particularly limited and may be appropriately adjusted depending on the thickness of the coating film of the sealant, etc.
  • the amount of light irradiation may be, for example, 50 mJ/cm 2 or more and 20,000 mJ/cm 2 or less, and preferably 100 mJ/cm 2 or more and 10,000 mJ/cm 2 or less.
  • the heating temperature is preferably 150°C or less, and more preferably 80°C or less, from the viewpoint of avoiding damage to light-emitting diode elements such as organic EL display elements.
  • the display device of the present embodiment includes a light-emitting diode element, a substrate, and a cured sealing layer formed by the cured body of the present embodiment and located between the light-emitting diode element and the substrate.
  • the light emitting diode element includes, for example, an organic electroluminescent display element or a micro LED, and preferably includes an organic electroluminescent display element.
  • the light emitting diode element may be in the form of a substrate with light emitting diode elements (TFT substrate), which is a substrate with projections and recesses.
  • the substrate is not particularly limited and may include, for example, one or more substrates selected from the group consisting of a color filter, a glass substrate, a silicon substrate, a plastic substrate, and the like, and preferably includes a color filter. Since the sealant of this embodiment has good coatability onto an uneven substrate, the effect of this embodiment can be obtained more effectively when a color filter, which is an uneven substrate, is used as the substrate.
  • the manufacturing method of the display device of the present embodiment may include, for example, a coating step of coating the sealant of the present embodiment on a first member, an irradiation step of irradiating the applied sealant with light, and a bonding step of bonding the first member and the second member via the light-irradiated sealant.
  • the bonding surfaces between the first member and the second member constituting the display device can be sealed with a cured sealing layer.
  • Examples of a method for applying the sealant of the present embodiment to the first member include coating film formation methods such as a solution coating method and a spray coating method, a flash deposition method, an inkjet method, etc. Among these, the inkjet method is preferred from the viewpoint of further improving productivity.
  • the thickness of the sealant applied to the first member is, for example, 1 ⁇ m to 15 ⁇ m, preferably 3 ⁇ m to 10 ⁇ m.
  • a film thickness of 15 ⁇ m or less leads to miniaturization of the display device, reduction in manufacturing costs, etc.
  • the sealant placed on the first member in the coating process thickens by light irradiation.
  • the first member and the second member are laminated together before the light-irradiated sealant hardens, so that the first member and the second member are bonded together by the sealant.
  • the sealant interposed between the first member and the second member is hardened by post-heating as necessary, forming a hardened seal layer.
  • the display device of this embodiment can also be manufactured by a method in which the sealant of this embodiment is applied onto a first member, a second member is attached via the sealant, and then the sealant is irradiated with light.
  • the steps after the irradiation step may be performed in a light-shielded state, so that the second member can be bonded to the first member without being exposed to light.
  • the first member and the second member are not particularly limited as long as they are members that constitute the display device.
  • the first member may be a light-emitting diode element
  • the second member may be a substrate.
  • the first member may be a substrate, and the second member may be a light-emitting diode element. That is, one of the first member and the second member may be a substrate, and the other may be a light-emitting diode element.
  • the solar cell of the present embodiment includes a solar cell, a substrate, and a cured encapsulation layer including the cured body of the present embodiment between the solar cell and the substrate.
  • the solar cell of the present embodiment preferably includes a perovskite solar cell.
  • composition of the present embodiment is a composition containing a cationic polymerizable compound (A), a cationic polymerization initiator (B), and a cure retarder (X), and in a viscosity measurement under the following measurement condition 1, when the viscosity 20 seconds after the start of the measurement is defined as V0 , 30 seconds after the start of the measurement, the non-alkali glass plate is irradiated with ultraviolet light having a wavelength of 365 nm and 30 mW/ cm2 perpendicularly toward the non-alkali glass plate from a point 15 cm away from the non-alkali glass plate for 20 seconds (total 600 mJ/ cm2 ), and the viscosity 60 seconds after the completion of the ultraviolet light irradiation is defined as V1 , the viscosity change rate represented by V1 / V0 is 1.00 or more and less than 1.75.
  • V1 cationic polymerizable compound
  • B cationic polymerization initiator
  • X cure retarder
  • the viscosity change rate represented by V1 / V0 is within the above range, it is possible to improve the coatability onto an uneven substrate such as a color filter or a substrate with a light-emitting diode element (TFT substrate). Since the composition of this embodiment easily spreads onto an uneven substrate without uneven coating, it is possible to suppress the remaining air bubbles in the coating film, and as a result, it is possible to form a cured layer with improved transparency on the uneven substrate.
  • the composition of the present embodiment is controlled so that the viscosity change rate represented by the above V1 / V0 is 1.00 or more and less than 1.75. This allows the composition of the present embodiment to have improved coatability onto a substrate having projections and recesses. The reason for this is not clear, but the following is thought to be the reason. First, it is believed that by having the viscosity change rate represented by the above V1 / V0 be equal to or higher than the lower limit, it is possible to prevent the coated droplets from excessively spreading and becoming non-uniform in thickness.
  • the coating film can be easily spread over the uneven surface of the substrate, thereby preventing air bubbles from remaining in the coating film and non-uniform thickness.
  • composition of the present embodiment can be produced by the same production method as the sealant of the present embodiment.
  • the composition of the present embodiment can be used, for example, as a sealant, an adhesive, a photosensitive resin layer, an insulating resin layer, a thermally conductive resin layer, a coating material, and the like.
  • Component (A1) Alicyclic compound having an epoxy group) (a1-1) 3',4'-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate ("Celloxide 2021P” manufactured by Daicel Chemical Industries, Ltd.) (a1-2) (3,3',4,4'-diepoxy)bicyclohexyl ("Celloxide 8010" manufactured by Daicel Chemical Industries, Ltd.)
  • a2-3) Dibromophenyl glycidyl ether (“BR-250H” manufactured by Nippon Kayaku Co., Ltd., molecular weight 308)
  • Component (A3): Glycidyl ether compound) (a3-1) Diglycidyl ether of 1,6-hexanediol ("ED-503G” manufactured by ADEKA Corporation) (a3-2) Diglycidyl ether of neopentyl glycol ("Denacol EX-211" manufactured by Nagase ChemteX Corporation)
  • b-1 Triarylsulfonium salt hexafluoroantimonate
  • ADEKA Optomer SP-170 Triarylsulfonium salt hexafluoroantimonate
  • b-2 Triarylsulfonium-tetrakispentafluorophenyl gallate
  • CPI-310FG Triarylsulfonium-tetrakispentafluorophenyl gallate
  • Component (C) Phosphate-based hardening retarder
  • c-1 Tris(2-ethylhexyl)phosphate
  • the sealants of the examples and comparative examples were subjected to viscosity measurement under the following measurement condition 1.
  • the viscosity 20 seconds after the start of the viscosity measurement was taken as V0
  • 30 seconds after the start of the measurement ultraviolet rays with a wavelength of 365 nm and 30 mW/ cm2 were irradiated perpendicularly toward the alkali-free glass plate from a point 15 cm away from the alkali-free glass plate for 20 seconds (total 600 mJ/ cm2 )
  • the viscosity 60 seconds after the completion of the ultraviolet irradiation was taken as V1
  • the viscosity 10 minutes after the completion of the ultraviolet irradiation was taken as V2 .
  • the ultraviolet irradiation was performed using an ultraviolet irradiation device (manufactured by HOYA, ultra-high pressure mercury lamp irradiation device "EXECURE3000") attached to the rheometer while continuously measuring the viscosity.
  • "at the start of measurement” means the time when the sample is set in the device and rotation starts.

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  • Physics & Mathematics (AREA)
  • Computer Hardware Design (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Power Engineering (AREA)
  • Materials Engineering (AREA)
  • Condensed Matter Physics & Semiconductors (AREA)
  • General Physics & Mathematics (AREA)
  • Manufacturing & Machinery (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

L'invention concerne un agent d'étanchéité comprenant : un composé polymérisable par voie cationique (A) ; un initiateur de polymérisation cationique (B) ; et un retardateur de durcissement (X), un rapport de changement de viscosité représenté par V1/V0 n'étant pas inférieur à 1,00 mais inférieur à 1,75, V0 représentant la viscosité 20 secondes après le début de la mesure de viscosité dans la condition de mesure 1, et V1 représentant la viscosité 60 secondes après l'achèvement de l'irradiation aux UV dans laquelle, après 30 secondes à partir du début de la mesure, une plaque de verre sans alcali est irradiée avec un faisceau de lumière ultraviolette ayant une longueur d'onde de 365 nm et à 30 mW/cm2 depuis un point situé à 15 cm à l'écart de la plaque de verre, dans une direction perpendiculaire à la plaque de verre pendant 20 secondes (un total de 600 mJ/cm2).
PCT/JP2023/039038 2022-11-04 2023-10-30 Agent d'étanchéité, corps durci, dispositif d'affichage, procédé de production de dispositif d'affichage, cellule solaire, et composition WO2024095948A1 (fr)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012090932A1 (fr) * 2010-12-27 2012-07-05 株式会社スリーボンド Composition d'étanchéité pour un élément de conversion photoélectrique
JP2016160415A (ja) * 2015-03-05 2016-09-05 横浜ゴム株式会社 導電性組成物、太陽電池セルおよび太陽電池モジュール
WO2020067046A1 (fr) * 2018-09-26 2020-04-02 デンカ株式会社 Agent d'étanchéité pour éléments d'affichage électroluminescents organiques
WO2020171186A1 (fr) * 2019-02-21 2020-08-27 デンカ株式会社 Composition

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012090932A1 (fr) * 2010-12-27 2012-07-05 株式会社スリーボンド Composition d'étanchéité pour un élément de conversion photoélectrique
JP2016160415A (ja) * 2015-03-05 2016-09-05 横浜ゴム株式会社 導電性組成物、太陽電池セルおよび太陽電池モジュール
WO2020067046A1 (fr) * 2018-09-26 2020-04-02 デンカ株式会社 Agent d'étanchéité pour éléments d'affichage électroluminescents organiques
WO2020171186A1 (fr) * 2019-02-21 2020-08-27 デンカ株式会社 Composition

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