WO2023182283A1 - Agent d'étanchéité et matériau d'étanchéité pour éléments électroluminescents organiques, dispositif d'affichage électroluminescent organique et procédé de production d'agent d'étanchéité pour éléments électroluminescents organiques - Google Patents

Agent d'étanchéité et matériau d'étanchéité pour éléments électroluminescents organiques, dispositif d'affichage électroluminescent organique et procédé de production d'agent d'étanchéité pour éléments électroluminescents organiques Download PDF

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Publication number
WO2023182283A1
WO2023182283A1 PCT/JP2023/010936 JP2023010936W WO2023182283A1 WO 2023182283 A1 WO2023182283 A1 WO 2023182283A1 JP 2023010936 W JP2023010936 W JP 2023010936W WO 2023182283 A1 WO2023182283 A1 WO 2023182283A1
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Prior art keywords
mass
meth
acrylate
sealant
radically polymerizable
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PCT/JP2023/010936
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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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Priority to JP2024510174A priority Critical patent/JPWO2023182283A1/ja
Publication of WO2023182283A1 publication Critical patent/WO2023182283A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
    • C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
    • G—PHYSICS
    • G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
    • G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
    • G09F9/00—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements
    • G09F9/30—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements in which the desired character or characters are formed by combining individual elements
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/02—Details
    • H05B33/04—Sealing arrangements, e.g. against humidity
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • 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
    • 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

Definitions

  • the present invention relates to a sealant for an organic electroluminescent device, a sealing material, an organic electroluminescent display device, and a method for manufacturing the sealant for an organic electroluminescent device.
  • Organic electroluminescent devices (hereinafter also referred to as organic EL devices) are attracting attention as device bodies that can emit light with high brightness.
  • organic EL elements have a problem in that they are degraded by oxygen and moisture, resulting in reduced light-emitting characteristics.
  • techniques for sealing organic EL elements and preventing deterioration are being considered.
  • Patent Document 1 describes a sealing method that contains a polymerizable compound and a polymerization initiator, has a viscosity of 5 to 50 mPa ⁇ s at 25°C, and has a surface tension of 15 to 35 mN/s at 25°C.
  • the encapsulant for organic EL elements is described, which has a water content of 1000 ppm or less at 25° C. after standing for 24 hours in an environment of 25° C. and 50% RH.
  • thermosetting encapsulants and photocurable encapsulants are known.
  • Photocurable encapsulants do not require heating during sealing, so they can form encapsulants without exposing organic EL elements to high heat, and have the advantage of suppressing deformation and deterioration of organic EL elements due to high heat. has.
  • an object of the present invention is to provide an encapsulant for organic EL elements that can significantly suppress the occurrence of dark spots under high temperature and high humidity conditions. Further, the present invention provides a sealant formed from the sealant for organic EL elements, an organic EL display device equipped with the sealant, and a method for manufacturing the sealant for organic EL elements. With the goal.
  • the present invention relates to, for example, the following ⁇ 1> to ⁇ 7>.
  • Organic electroluminescence containing a radically polymerizable compound, a photopolymerization initiator, and a stable radical-type compound having a stable radical, and having an acid value of 0.01 to 0.15 (mgKOH/g) Encapsulant for elements.
  • a sealing material comprising a cured product of the sealant according to ⁇ 1> or ⁇ 2>.
  • An organic electroluminescent display device comprising an organic electroluminescent element and the sealing material according to ⁇ 3>, which seals the organic electroluminescent element.
  • a method for producing a sealant for an organic electroluminescent device comprising:
  • an encapsulant for organic EL elements that can significantly suppress the occurrence of dark spots under high temperature and high humidity conditions. Further, according to the present invention, there is provided a sealant formed from the sealant for organic EL elements, an organic EL display device including the sealant, and a method for manufacturing the sealant for organic EL elements. be done.
  • X to Y in the description of numerical ranges means from X to Y, unless otherwise specified.
  • “1 to 5% by mass” means “1 to 5% by mass”.
  • alkyl group includes not only an alkyl group having no substituent (unsubstituted alkyl group) but also an alkyl group having a substituent (substituted alkyl group).
  • (meth)acrylic includes both acrylic and methacrylic.
  • the sealant of this embodiment contains a radically polymerizable compound, a photopolymerization initiator, and a stable radical type compound having a stable radical. Further, the sealant of this embodiment has an acid value of 0.01 to 0.15 (mgKOH/g).
  • the sealant of this embodiment is for sealing an organic electroluminescent element. That is, the sealant of this embodiment is used to seal an organic EL element and manufacture an organic EL display device.
  • the sealant of this embodiment is a photocurable sealant because it contains a photopolymerization initiator.
  • the reason why the sealant of this embodiment achieves the above effects is not necessarily limited, the following reasons can be considered.
  • conventional encapsulants contain a trace amount of acid component in the encapsulant formed by curing the encapsulant, and due to the presence of the acid component, the sealant is When moisture enters the sealing material, the sealing material may deteriorate due to hydrolysis, resulting in a decrease in reliability.
  • the encapsulant of this embodiment has an acid value of 0.15 mgKOH/g or less, there is little residual acid component in the encapsulant, and even if a small amount of moisture enters the encapsulant, the encapsulant will remain intact. Hydrolysis of the stopper material is less likely to occur. Therefore, according to the sealant of the present embodiment, it is possible to form a sealant that does not easily deteriorate even under high temperature and high humidity conditions, and it is possible to suppress the occurrence of dark spots due to deterioration of the sealant.
  • the sealant of this embodiment has an acid value of 0.01 mgKOH/g or more and contains an extremely small amount of acid component.
  • this extremely small amount of acid component acts as a polymerization inhibitor, making the sealant excellent in storage stability, and suppressing a decrease in reliability due to deterioration of the sealant during storage. it is conceivable that.
  • the sealant of this embodiment has excellent discharge properties from the coating device. Specifically, according to the sealant of this embodiment, when the sealant is discharged from the coating device, bending of the discharged liquid, variation in the amount of the discharged liquid, etc. are suppressed, and good dischargeability is maintained. As a result, according to the sealant of the present embodiment, a coating film with significantly less uneven thickness and excellent flatness can be formed. Moreover, according to the encapsulant of this embodiment, it is possible to form a encapsulant that contributes to improving the reliability of organic EL elements.
  • the reason why the sealant of this embodiment achieves the above effects is not necessarily limited, the following reasons can be considered. According to the findings of the present inventors, with conventional photocurable sealants, when the sealant is discharged from the coating device, bending of the discharged liquid, variations in the amount of discharged liquid, etc. occur, and this causes the coating to be applied. There were cases where the film became uneven in thickness and the flatness of the coating film decreased. The reason for this is that photocurable sealants tend to undergo unintentional polymerization before use (for example, during storage, transportation, etc.), and the fine particles generated by the polymerization may flow through the coating equipment.
  • the sealant of this embodiment contains a stable radical type compound, so that although it is a photocurable sealant, there is no possibility of unintentional polymerization before use (for example, during storage, transportation, etc.) or due to the polymerization. Generation of particles is significantly suppressed. Therefore, with the sealant of the present embodiment, coating defects caused by particles are suppressed, and excellent discharge properties from the coating device and high flatness of the coated film after coating are achieved.
  • the reliability of the organic EL device may be lowered due to the intrusion of water or oxygen through the cracks.
  • the sealant of this embodiment contains a stable radical type compound, the above-mentioned reaction points are unlikely to remain in the cured product, and further polymerization from the reaction points is also suppressed. Therefore, according to the encapsulant of this embodiment, deterioration due to reaction points is difficult to occur, damage to the inorganic protective film due to curing shrinkage can be suppressed, and the encapsulant contributes to improving the reliability of organic EL elements. Can be formed.
  • the radically polymerizable compound may be any compound that can be polymerized by active species generated from the photopolymerization initiator described below.
  • One type of radically polymerizable compound may be used alone, or two or more types may be used in combination.
  • a radically polymerizable compound can be said to be a compound having a radically polymerizable group.
  • the radically polymerizable group include a vinyl group, a (meth)acryloyl group, an allyl group, a vinyl ether group, a vinyl ester group, a (meth)acrylamide group, and among these, a (meth)acryloyl group is particularly preferred.
  • the radically polymerizable compound preferably includes, for example, a polyfunctional compound having two or more radically polymerizable groups.
  • the number of radically polymerizable groups in the polyfunctional compound may be, for example, 2 to 6, preferably 2 to 4.
  • photocurability tends to be further improved.
  • the polyfunctional compound is preferably a bifunctional compound having two radically polymerizable groups.
  • the radically polymerizable compound may include a monofunctional compound having one radically polymerizable group. From the viewpoint of easy adjustment of the polymerization rate, physical properties of the cured product, etc., the radically polymerizable compound preferably contains a polyfunctional compound and a monofunctional compound.
  • the proportion of the polyfunctional compound in the radically polymerizable compound may be, for example, 30% by mass or more, preferably 50% by mass or more, and more preferably 60% by mass or more.
  • the content is at least 70% by mass, more preferably at least 80% by mass, and may be at least 85% by mass or at least 90% by mass.
  • the proportion of the polyfunctional compound in the polymerizable compound may be, for example, 100% by mass or less, and preferably 95% by mass or less.
  • the proportion of the polyfunctional compound in the radically polymerizable compound is, for example, 30 to 100% by mass, 30 to 95% by mass, 50 to 100% by mass, 50 to 95% by mass, 60 to 100% by mass, 60 to 95% by mass. %, 70-100% by mass, 70-95% by mass, 80-100% by mass, 80-95% by mass, 85-100% by mass, 85-95% by mass, 90-100% by mass or 90-95% by mass. There may be.
  • polyfunctional (meth)acrylic compound having two or more (meth)acryloyl groups is preferred.
  • polyfunctional (meth)acrylic compounds include: Bis(1-(meth)acryloxy-2-hydroxypropyl) phthalate, bis(2-(meth)acryloxyethyl) phosphate, bis((meth)acryloxy-2-hydroxypropyloxy) diethylene glycol, bisphenol A di(meth) acrylate, bisphenol A di-(3-(meth)acryloxyethyl) ether, bisphenol A di-(3-(meth)acryloxy-2-hydroxypropyl) ether, 1,3-butanediol di(meth)acrylate, 1 , 4-butanediol di-(3-(meth)acryloxy-2-hydroxypropyl) ether, 1,4-butanediol di(meth)acrylate, 1,3-butanediol bis((meth)acryloxypropionate
  • a monofunctional (meth)acrylic compound having one (meth)acryloyl group is preferable.
  • monofunctional (meth)acrylic compounds include methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, n-butyl (meth)acrylate, t-butyl (meth)acrylate, and hexyl (meth)acrylate.
  • acrylate 2-ethylhexyl (meth)acrylate, nonyl (meth)acrylate, benzyl (meth)acrylate, glycidyl (meth)acrylate, cyclohexyl (meth)acrylate, lauryl (meth)acrylate, n-octyl (meth)acrylate, 2 -Methoxyethyl (meth)acrylate, butoxyethyl (meth)acrylate, methoxytetraethylene glycol (meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 3-chloro-2-hydroxypropyl (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, 2-hydroxy-3-phenoxypropyl (meth)acrylate (2-HPA), dicyclopentenyl (meth)acrylate, dicyclopentenyloxyethyl (meth)acrylate, Cyclopent
  • the radically polymerizable compound preferably contains a compound having an aromatic ring (hereinafter also referred to as an aromatic monomer). This tends to further reduce the moisture permeability of the cured product.
  • the proportion of the aromatic monomer in the radically polymerizable compound may be, for example, 1% by mass or more, preferably 2% by mass or more, more preferably 3% by mass or more. The content may be 5% by mass or more. Further, the proportion of the aromatic monomer in the radically polymerizable compound may be, for example, 70% by mass or less, preferably 60% by mass or less, more preferably 50% by mass or less, still more preferably 40% by mass or less, It may be 30% by mass or less, 20% by mass or less, 15% by mass or less, or 10% by mass or less.
  • the proportion of the aromatic monomer in the radically polymerizable compound is, for example, 1 to 70% by mass, 1 to 60% by mass, 1 to 50% by mass, 1 to 40% by mass, 1 to 30% by mass, 1 to 20% by mass. %, 1-15% by mass, 1-10% by mass, 2-70% by mass, 2-60% by mass, 2-50% by mass, 2-40% by mass, 2-30% by mass, 2-20% by mass, 2-15% by mass, 2-10% by mass, 3-70% by mass, 3-60% by mass, 3-50% by mass, 3-40% by mass, 3-30% by mass, 3-20% by mass, 3- 15% by mass, 3-10% by mass, 5-70% by mass, 5-60% by mass, 5-50% by mass, 5-40% by mass, 5-30% by mass, 5-20% by mass, 5-15% by mass % or 5 to 10% by mass.
  • aromatic monomers examples include: Benzyl (meth)acrylate, 4-butylphenyl (meth)acrylate, phenyl (meth)acrylate, 2,4,5-tetramethylphenyl (meth)acrylate, 4-chlorophenyl (meth)acrylate, phenoxymethyl (meth)acrylate, Phenoxyethyl (meth)acrylate, 2-hydroxy-3-phenoxypropyl (meth)acrylate (2-HPA), 2-(meth)acryloyloxyhexahydrophthalic acid, 2-(meth)acryloyloxyethyl-2- Hydroxypropylphthalic acid, EO-modified phenol (meth)acrylate, EO-modified cresol (meth)acrylate, EO-modified nonylphenol (meth)acrylate, PO-modified nonylphenol (meth)acrylate, ethoxylated-o-phenylphenol (meth)acrylate, m - Compounds having one aromatic ring such
  • the aromatic monomer is preferably a compound having two or more aromatic rings.
  • the radically polymerizable compound is at least one selected from the group consisting of ethoxylated-o-phenylphenol (meth)acrylate, m-phenoxybenzyl (meth)acrylate, and ethoxylated bisphenol A di(meth)acrylate as an aromatic monomer. It is more preferable to contain at least one selected from the group consisting of ethoxylated-o-phenylphenol (meth)acrylate and ethoxylated bisphenol A di(meth)acrylate.
  • the radically polymerizable compound includes an alicyclic monomer having a radically polymerizable group and an aliphatic hydrocarbon ring.
  • the aliphatic hydrocarbon ring possessed by the alicyclic monomer may be a monocyclic ring or a fused ring. Further, the aliphatic hydrocarbon ring may be a saturated hydrocarbon ring or an unsaturated hydrocarbon ring.
  • the saturated hydrocarbon ring may be a cycloalkane ring. Examples of the unsaturated aliphatic hydrocarbon ring include a cycloalkene ring, a cycloalkadiene ring, and a cycloalkatriene ring, with the cycloalkene ring being preferred.
  • cycloalkane ring examples include a cyclopentane ring, a cyclohexane ring, a tetrahydrodicyclopentadiene ring, a cycloheptane ring, a cyclooctene ring, a norbornane ring, and an adamantane ring.
  • Examples of the cycloalkene ring include a cyclopentene ring, a cyclohexene ring, a dihydrodicyclopentadiene ring, a cycloheptene ring, a cyclooctene ring, and a norbornene ring.
  • the cycloalkene ring is preferably a cyclopentene ring, a cyclohexene ring, or a dihydrodicyclopentadiene ring, which has a large ring strain, and is preferably a cyclopentene ring or a dihydrodicyclopentadiene ring. It is more preferable that there be.
  • the alicyclic monomer may be a monofunctional compound having one radically polymerizable group, or may be a polyfunctional compound having two or more radically polymerizable groups.
  • the number of radically polymerizable groups in the alicyclic monomer may be, for example, 1 to 6, preferably 1 to 4, more preferably 1 to 3, and still more preferably 1 to 2.
  • the alicyclic monomer may be a compound having one aliphatic hydrocarbon ring, or may be a compound having two or more aliphatic hydrocarbon rings.
  • the number of aliphatic hydrocarbon rings in the alicyclic monomer may be, for example, 1 to 6, preferably 1 to 4, more preferably 1 to 3, even more preferably 1 to 2.
  • alicyclic monomer for example, Saturated alicyclic monomers such as tricyclodecane dimethanol di(meth)acrylate, 1,4-cyclohexanediol di(meth)acrylate, cyclohexyl(meth)acrylate, dicyclopentanyl(meth)acrylate;
  • unsaturated alicyclic monomers such as dicyclopentenyl (meth)acrylate and dicyclopentenyloxyethyl (meth)acrylate.
  • the proportion of the alicyclic monomer in the radically polymerizable compound may be, for example, 3% by mass or more, preferably 5% by mass or more, more preferably 10% by mass or more, and still more preferably 15% by mass or more. Further, the proportion of the alicyclic monomer in the radically polymerizable compound may be, for example, 90% by mass or less, preferably 70% by mass or less, more preferably 50% by mass or less, still more preferably 40% by mass or less. . That is, the proportion of the alicyclic monomer in the radically polymerizable compound is, for example, 3 to 90% by mass, 3 to 70% by mass, 3 to 50% by mass, 3 to 40% by mass, 5 to 90% by mass, 5 to 70% by mass. Mass%, 5-50 mass%, 5-40 mass%, 10-90 mass%, 10-70 mass%, 10-50 mass%, 10-40 mass%, 15-90 mass%, 15-70 mass% , 15 to 50% by weight, or 15 to 40% by weight.
  • the radically polymerizable compound preferably contains an acyclic monomer that has a radically polymerizable group and does not have a ring structure.
  • the number of radically polymerizable groups that the acyclic monomer has may be, for example, one or more, and preferably two or more.
  • the number of radically polymerizable groups that the acyclic monomer has may be, for example, 6 or less, preferably 4 or less, and more preferably 3 or less. It is particularly preferable that the acyclic monomer has two radically polymerizable groups. That is, the number of radically polymerizable groups that the acyclic monomer has may be, for example, 1 to 6, 1 to 4, 1 to 3, 2 to 6, 2 to 4, or 2 to 3.
  • Examples of the acyclic monomer include compounds having a radically polymerizable group and a chain saturated hydrocarbon group (hereinafter also referred to as a chain monomer).
  • the number of carbon atoms in the chain saturated hydrocarbon group contained in the chain monomer is, for example, 2 or more, and may be 3 or more, 4 or more, 6 or more, 8 or more, or 10 or more.
  • the number of carbon atoms in the chain saturated hydrocarbon group contained in the chain monomer may be, for example, 16 or less, 15 or less, 14 or less, or 13 or less.
  • the number of carbon atoms in the chain saturated hydrocarbon group possessed by the chain monomer is, for example, 2 to 16, 2 to 15, 2 to 14, 2 to 13, 3 to 16, 3 to 15, 3 to 14, 3 to 13 , 4-16, 4-15, 4-14, 4-13, 6-16, 6-15, 6-14, 6-13, 8-16, 8-15, 8-14, 8-13, 10 -16, 10-15, 10-14 or 10-13.
  • the chain saturated hydrocarbon group possessed by the chain monomer is preferably an alkanediyl group.
  • the preferred range of the carbon number of the alkanediyl group is the same as the preferred range of the carbon number of the chain saturated hydrocarbon group.
  • the proportion of the chain monomer in the radically polymerizable compound may be, for example, 10% by mass or more, preferably 20% by mass or more, and more preferably 30% by mass or more.
  • the content may be 40% by mass or more, 50% by mass or more, or 55% by mass or more.
  • the proportion of the chain monomer in the radically polymerizable compound may be, for example, 90% by mass or less, preferably 85% by mass or less, and more preferably 80% by mass or less.
  • the proportion of the chain monomer in the radical polymerizable compound is, for example, 10 to 90% by mass, 10 to 85% by mass, 10 to 80% by mass, 20 to 90% by mass, 20 to 85% by mass, 20 to 80% by mass. %, 30-90 mass%, 30-85 mass%, 30-80 mass%, 40-90 mass%, 40-85 mass%, 40-80 mass%, 50-90 mass%, 50-85 mass%, It may be 50-80% by weight, 55-90% by weight, 55-85% by weight or 55-80% by weight.
  • chain monomers include: 1,4-butanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,7-heptanediol di(meth)acrylate, 1,8-octanediol di(meth)acrylate, 1, 9-nonanediol di(meth)acrylate, 1,10-decanediol di(meth)acrylate, 1,12-dodecanediol di(meth)acrylate, 1,13-tridecanediol di(meth)acrylate, 1,14 -Tetradecanediol di(meth)acrylate, 1,15-pentadecanediol di(meth)acrylate, 1,16-hexadecanediol di(meth)acrylate, neopentyl glycol dimethacrylate, 1,12-dodecanediol di(meth)acrylate
  • the radically polymerizable compound preferably contains a compound having a fluoro group (hereinafter also referred to as a fluorine-containing monomer).
  • a fluorine-containing monomer a compound having a fluoro group
  • the proportion of the fluorine-containing monomer in the radically polymerizable compound may be, for example, 0.1% by mass or more, preferably 0.3% by mass or more, and more preferably 0. .5% by mass or more, and may be 0.7% by mass or more, 0.9% by mass or more, or 1% by mass or more. Further, the proportion of the fluorine-containing monomer in the radically polymerizable compound may be, for example, 15% by mass or less, preferably 10% by mass or less, 7% by mass or less, 5% by mass or less, 3% by mass or less, or 2% by mass or less. It may be less than % by mass.
  • the proportion of the fluorine-containing monomer in the radically polymerizable compound is, for example, 0.1 to 15% by mass, 0.1 to 10% by mass, 0.1 to 7% by mass, 0.1 to 5% by mass, 0. 1-3 mass%, 0.1-2 mass%, 0.3-15 mass%, 0.3-10 mass%, 0.3-7 mass%, 0.3-5 mass%, 0.3- 3% by mass, 0.3-2% by mass, 0.5-15% by mass, 0.5-10% by mass, 0.5-7% by mass, 0.5-5% by mass, 0.5-3% by mass %, 0.5-2% by mass, 0.7-15% by mass, 0.7-10% by mass, 0.7-7% by mass, 0.7-5% by mass, 0.7-3% by mass, 0.7-2% by mass, 0.9-15% by mass, 0.9-10% by mass, 0.9-7% by mass, 0.9-5% by mass, 0.9-3% by mass, 0. It may be 9-2% by weight, 1-15% by weight, 1-10% by weight, 1-7% by weight,
  • the number of fluoro groups that the fluorine-containing monomer has may be, for example, 1 or more, preferably 2 or more, and more preferably 3 or more. Further, the number of fluoro groups that the fluorine-containing monomer has is not particularly limited, but may be, for example, 40 or less, and preferably 30 or less. That is, the number of fluoro groups that the fluorine-containing monomer has may be, for example, 1 to 40, 1 to 30, 2 to 40, 2 to 30, 3 to 40, or 3 to 30.
  • the content of fluorine atoms based on the total amount of the fluorine-containing monomer may be, for example, 1% by mass or more, preferably 2% by mass or more, and more preferably 5% by mass or more.
  • a fluorine-containing monomer that satisfies such a content range exhibits the above-mentioned effects more markedly.
  • the content of fluorine atoms based on the total amount of the fluorine-containing monomer may be, for example, 75% by mass or less, preferably 70% by mass or less, and more preferably 65% by mass or less.
  • the content of fluorine atoms relative to the total amount of the fluorine-containing monomer is, for example, 1 to 75% by mass, 1 to 70% by mass, 1 to 65% by mass, 2 to 75% by mass, 2 to 70% by mass, 2 to 65% by mass. %, 5-75% by weight, 5-70% by weight or 5-65% by weight.
  • the number of radically polymerizable groups that the fluorine-containing monomer has may be one or more. From the viewpoint of easily obtaining a cured product with a low glass transition temperature, the number of radically polymerizable groups contained in the fluorine-containing monomer may be one. Further, from the viewpoint of easily obtaining a cured product having a high glass transition temperature, the number of radically polymerizable groups contained in the fluorine-containing monomer may be 2 or more. There is no particular upper limit to the number of radically polymerizable groups that the fluorine-containing monomer has. The number of radically polymerizable groups that the fluorine-containing monomer has is, for example, 4 or less, preferably 3 or less, more preferably 2 or less from the viewpoint of easily obtaining a cured product with excellent flexibility.
  • fluorine-containing monomer examples include 2,2,2-trifluoroethyl (meth)acrylate, 2,2,3,3-tetrafluoropropyl (meth)acrylate, and 1H,1H,5H-octafluoropentyl (meth)acrylate.
  • the photopolymerization initiator may be any initiator that can polymerize the above-mentioned radically polymerizable compound.
  • One type of photopolymerization initiator may be used alone, or two or more types may be used in combination.
  • photopolymerization initiator for example, Benzophenone and its derivatives; Benzyl and its derivatives; Anthraquinone and its derivatives; Benzoin-type photopolymerization initiators such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin propyl ether, benzoin isobutyl ether, benzyl dimethyl ketal; Acetophenone type photopolymerization initiator such as diethoxyacetophenone and 4-tert-butyltrichloroacetophenone; 2-dimethylaminoethylbenzoate; p-dimethylaminoethylbenzoate; Diphenyl disulfide; Thioxanthone and its derivatives; Camphorquinone, 7,7-dimethyl-2,3-dioxobicyclo[2.2.1]heptane-1-carboxylic acid, 7,7-dimethyl-2,3-dioxobicycl
  • an acylphosphine oxide type photopolymerization initiator is preferable because it can be cured using only visible light of 390 nm or more and can be cured without damaging the organic EL element.
  • an acylphosphine oxide type photopolymerization initiator 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide is preferred because it further improves the transparency of the cured product and can be cured using only light of 395 nm or more. is preferred.
  • Examples of the 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide include "Omnirad TPO" manufactured by IGM Resins.
  • the content of the photopolymerization initiator may be, for example, 0.05 parts by mass or more, preferably 0.5 parts by mass or more, more preferably 1 part by mass or more, based on 100 parts by mass of the radically polymerizable compound. Preferably it is 2 parts by mass or more. Further, the content of the photopolymerization initiator may be, for example, 10 parts by mass or less, preferably 8 parts by mass or less, and more preferably 5 parts by mass or less, based on 100 parts by mass of the radically polymerizable compound. Such a content tends to ensure sufficient transparency of the encapsulant while obtaining sufficient sensitivity and curing speed of the encapsulant.
  • the content of the photopolymerization initiator is, for example, 0.05 to 10 parts by mass, 0.05 to 8 parts by mass, 0.05 to 5 parts by mass, or 0.5 parts by mass with respect to 100 parts by mass of the radically polymerizable compound. ⁇ 10 parts by weight, 0.5 to 8 parts by weight, 0.5 to 5 parts by weight, 1 to 10 parts by weight, 1 to 8 parts by weight, 1 to 5 parts by weight, 2 to 10 parts by weight, 2 to 8 parts by weight Alternatively, it may be 2 to 5 parts by mass.
  • a stable radical type compound is a compound having a stable radical.
  • One type of photopolymerization initiator may be used alone, or two or more types may be used in combination.
  • a nitroxide radical (NO radical) is preferable. That is, as the stable radical type compound, a compound having a nitroxide radical is preferable. Since nitroxide radicals have excellent compatibility and reactivity with radically polymerizable compounds, they can quickly capture radical species.
  • organic EL elements are degraded by oxygen, they are managed at a low oxygen concentration of less than 1 ppm, and the sealant for organic EL elements is also used at a low oxygen concentration.
  • the general phenolic antioxidant used for inhibiting the polymerization of radically polymerizable compounds requires a reaction with oxygen in the process of exhibiting the polymerization inhibiting function. For this reason, it is difficult for phenolic antioxidants to exhibit a polymerization inhibiting function in sealants for organic EL elements.
  • stable radical-type compounds having stable radicals can capture radical species regardless of the presence or absence of oxygen, and therefore can significantly obtain the above-mentioned effects.
  • stable radical type compounds include 1-oxyl-2,2,6,6-tetramethylpiperidine, 4-hydroxy-2,2,6,6-tetramethylpiperidine 1-oxyl, and 4-(meth)acryloyl.
  • Examples include oxy-2,2,6,6-tetramethylpiperidine-1-oxyl, and 4-(meth)acryloyloxy-2,2,6,6 from the viewpoint of being less likely to be incorporated into the cured product and cause outgassing.
  • -Tetramethylpiperidine 1-oxyl is preferred, and 4-methacryloyloxy-2,2,6,6-tetramethylpiperidine 1-oxyl is more preferred.
  • the content of the stable radical type compound may be, for example, 1 mass ppm or more, preferably 10 mass ppm or more, more preferably 50 mass ppm or more, and even more preferably 100 mass ppm, based on 100 parts by mass of the radically polymerizable compound. ppm or more. Further, the content of the stable radical type compound may be, for example, 15,000 mass ppm or less, preferably 10,000 mass ppm or less, more preferably 8,000 mass ppm or less, and even more preferably It is 6000 mass ppm or less.
  • the content of the stable radical type compound is, for example, 1 to 15,000 mass ppm, 1 to 10,000 mass ppm, 1 to 8,000 mass ppm, 1 to 6,000 mass ppm, 10 to 15,000 mass ppm with respect to 100 parts by mass of the radically polymerizable compound.
  • the sealant of this embodiment may further contain other components than those mentioned above.
  • Other components include antioxidants, surfactants, sensitizers, and the like.
  • the content of other components is not particularly limited, and may be, for example, 10 parts by mass or less, preferably 5 parts by mass or less, more preferably 3 parts by mass or less, based on 100 parts by mass of the radically polymerizable compound. It may be 2 parts by mass or less or 1 part by mass or less.
  • the viscosity of the sealant of this embodiment is preferably 3 mPa ⁇ s or more, more preferably 5 mPa ⁇ s or more. Further, the viscosity of the sealant of this embodiment is preferably 50 mPa ⁇ s or less, more preferably 30 mPa ⁇ s or less. When the viscosity of the sealant is within the above range, the ejection properties during application by an inkjet method tend to be further improved, and coating film formation tends to be easier. That is, the viscosity of the sealant may be, for example, 3 to 50 mPa ⁇ s, 3 to 30 mPa ⁇ s, 5 to 50 mPa ⁇ s, or 5 to 30 mPa ⁇ s.
  • the viscosity of the sealant indicates a value measured at 25° C. and 250 rpm using a cone-plate viscometer (manufactured by Eiko Seiki Co., Ltd., product number: HB DV3T, etc.).
  • the sulfur atom concentration of the sealant of this embodiment may be, for example, 100 ppm or less, preferably 50 ppm or less, and more preferably 40 ppm or more.
  • the sulfur atom concentration of the sealant of this embodiment may also be, for example, 0.1 ppm or more, or 1 ppm or more. That is, the sulfur atom concentration of the sealant of this embodiment may be, for example, 0.1 to 100 ppm, 0.1 to 50 ppm, 0.1 to 40 ppm, 1 to 100 ppm, 1 to 50 ppm, or 1 to 40 ppm. .
  • a sulfur atom concentration With such a sulfur atom concentration, deterioration of the organic EL element and generation of dark spots are more significantly suppressed, and reliability tends to be further improved.
  • the water concentration of the sealant of this embodiment may be, for example, 100 ppm or less, preferably 70 ppm or less, and more preferably 50 ppm or less.
  • the water concentration of the sealant of this embodiment may also be, for example, 0.5 ppm or more, or 1 ppm or more. That is, the moisture concentration of the sealant of this embodiment may be, for example, 0.5 to 100 ppm, 0.5 to 70 ppm, 0.5 to 50 ppm, 1 to 100 ppm, 1 to 70 ppm, or 1 to 50 ppm. At such a water concentration, the above-mentioned effects tend to be more pronounced.
  • the number of particles with a diameter of 1 ⁇ m or more existing in 1 mL of the sealant of this embodiment is a
  • the number of particles with a diameter of 1 ⁇ m or more existing in 1 mL of the sealant after heating at 80 ° C. for 16 hours is a.
  • ba is preferably 10 or less. According to such a sealant, coating defects caused by particles are suppressed, and excellent discharge performance from the coating device and high flatness of the coated film after coating are realized.
  • the above a is preferably 10 or less, more preferably 5 or less, even more preferably 3 or less, and may be 0.
  • the above b is preferably 10 or less, more preferably 5 or less, even more preferably 3 or less, and may be 0.
  • the sealant of this embodiment may contain particles of 1 ⁇ m or more, but preferably does not contain particles (that is, a is 0).
  • particles include particles derived from polymers of radically polymerizable compounds, particles derived from foreign substances such as dust, particles derived from dehydrating agents such as molecular sieves used in the manufacturing process of sealants, etc. .
  • the sealant of this embodiment may be a sealant that does not substantially contain these particles, and the particles may be removed using a filtration filter or the like.
  • the number of particles indicates a value measured using a particle counter (manufactured by Rion Corporation, light scattering particle detector in liquid, product number: KS-42B).
  • the acid value of the sealant of this embodiment is 0.15 (mgKOH/g) or less, preferably 0.13 (mgKOH/g) or less, more preferably 0.10 (mgKOH/g) or less. . Thereby, the above-mentioned effects are more prominently produced. Further, the acid value of the sealant of this embodiment is 0.01 (mgKOH/g) or more, preferably 0.015 (mgKOH/g) or more, more preferably 0.02 (mgKOH/g) or more. It is. Thereby, the effect of the acid component as a polymerization inhibitor is more prominently exhibited.
  • the acid value of the sealant of this embodiment is, for example, 0.01 to 0.15 (mgKOH/g), 0.01 to 0.13 (mgKOH/g), or 0.01 to 0.10 (mgKOH/g). /g), 0.015 to 0.15 (mgKOH/g), 0.015 to 0.13 (mgKOH/g), 0.015 to 0.10 (mgKOH/g), 0.02 to 0.15 (mgKOH/g), 0.02 to 0.13 (mgKOH/g), or 0.02 to 0.10 (mgKOH/g).
  • the acid value of the sealant of this embodiment shows the value measured by the following method. Weigh 2 g of the sample into a 50 mL tall beaker, add 40 mL of 2-propanol, and stir for 5 minutes. After confirming the stability of the potential, the end point was determined by potentiometric titration using a titrant 0.1 mol/L 2-propanolic potassium hydroxide standard solution (manufactured by Wako Pure Chemical Industries, Ltd.) using an automatic titrator COM 550 manufactured by Hiranuma Seisakusho. demand.
  • the method for manufacturing the sealant of this embodiment is not particularly limited, it can be manufactured, for example, by the following method.
  • Method for manufacturing sealant In the method for producing a sealant of the present embodiment, at least a part of the radically polymerizable compound is added to the following (i) so that the acid value of the sealant is 0.01 to 0.15 (mgKOH/g). and a mixing step of mixing a radically polymerizable compound, a photopolymerization initiator, and a stable radical-type compound having a stable radical to obtain a sealant.
  • the pretreatment step may further include pretreatment by methods (ii) and (iii). (i) Degassing treatment in an environment of 10 to 100°C and 1000 Pa or less (ii) Distillation purification (iii) Column chromatography purification
  • the acid value of the sealant is due to a trace amount of acid component in the radically polymerizable compound. Therefore, in the manufacturing method of this embodiment, the acid value of the sealant is adjusted to a specific range by pretreating the radically polymerizable compound in the pretreatment step.
  • the pretreatment method in the pretreatment step includes (i) and may further include either (ii) or (iii).
  • the pretreatment method (i) is a method of degassing the radically polymerizable compound.
  • each radically polymerizable compound may be individually degassed, or multiple types of radically polymerizable compounds may be simultaneously degassed (multiple types of The mixture of radically polymerizable compounds may be subjected to deaeration treatment).
  • the temperature in the degassing treatment is 10 to 100°C, preferably 30 to 90°C, and more preferably 40 to 80°C.
  • the pressure in the degassing treatment is 1000 Pa or less, preferably 800 Pa or less, more preferably 500 Pa or less. Further, the pressure in the degassing process may be, for example, 1 Pa or more, or 10 Pa or more. That is, the pressure in the deaeration process may be, for example, 1 to 1000 Pa, 1 to 800 Pa, 1 to 500 Pa, 10 to 1000 Pa, 10 to 800 Pa, or 10 to 500 Pa.
  • the degassing treatment can be carried out, for example, in a container equipped with a stirring means and connected to a vacuum pump and a vacuum gauge.
  • air bubbling air blowing
  • the degassing treatment may be carried out, for example, in a container equipped with a stirring means and connected to a vacuum pump and a vacuum gauge.
  • air bubbling air blowing
  • the pretreatment method (ii) is a method of purifying the radically polymerizable compound by distillation.
  • Suitable conditions for distillation purification include, for example, a temperature of 10 to 100°C and a pressure of 0.1 MPa or less.
  • distillation purification include the following methods. Note that the distillation purification method is not limited to the following method, and may be appropriately selected from known distillation purification methods.
  • the radically polymerizable compound was heated at a pressure of 0.05 MPa and a rotational speed of 50 r/min in a hot bath adjusted to 65°C using a rotary distillation apparatus (manufactured by Tokyo Rika Kikai Co., Ltd., "Rotary Evaporator N-1000S"). Distill for 3 hours.
  • the pretreatment method (iii) is a method of purifying a radically polymerizable compound by column chromatography.
  • column chromatography purification examples include column chromatography purification using silica gel as an adsorbent.
  • column chromatography purification examples include the following method.
  • the column chromatography purification method is not limited to the following method, and may be appropriately selected from known column chromatography purification methods.
  • pretreatment is performed so that the acid value of the sealant is 0.01 to 0.15 (mgKOH/g).
  • the pretreatment conditions may be adjusted as appropriate depending on the amount of the radically polymerizable compound in the sealant. That is, in the pretreatment step, the pretreatment conditions and the like may be adjusted as appropriate depending on the predetermined composition of the sealant.
  • the mixing step is a step of mixing a radically polymerizable compound, a photopolymerization initiator, and a stable radical-type compound having a stable radical to obtain a sealant.
  • the mixing method in the mixing step is not particularly limited, and examples thereof include methods such as mixing using a stirrer such as a three-one motor and mixing using a mix rotor.
  • Suitable mixing conditions in the mixing step include, for example, mixing at a temperature of 15 to 40° C. for 1 hour or more.
  • a cured product containing a polymer of a radically polymerizable compound can be obtained.
  • This cured product may contain a stable radical as a stable radical type compound or a reactant thereof.
  • This cured product can be suitably used as a sealing material for organic EL elements.
  • the sealant of this embodiment can be cured by light irradiation.
  • the light source used for curing the sealant of this embodiment is not particularly limited. Examples of light sources 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. can be mentioned.
  • the above light sources have different emission wavelengths and energy distributions. Therefore, the light source may be appropriately selected depending on the reaction wavelength of the photopolymerization initiator. Natural light (sunlight) can also be a light source for initiating the reaction.
  • Irradiation by a light source may be direct irradiation, or may be focused irradiation using a reflecting mirror, fiber, etc. Alternatively, irradiation may be performed using a low wavelength cut filter, a heat ray cut filter, a cold mirror, or the like.
  • Examples of the method for sealing an organic EL element using the sealant of this embodiment include the following sealing method.
  • a substrate on which an organic EL element is installed is prepared, and a sealant is applied on the surface of the substrate on which the organic EL element is installed to form a coating film of the sealant.
  • the coating film is irradiated with light to form a sealant made of a cured sealant.
  • the organic EL element is sealed with the sealing material.
  • an inkjet method for applying the sealant.
  • an organic EL display device it is necessary to apply a sealant onto a large-area substrate on which a plurality of organic EL elements are installed.
  • the sealant of this embodiment can be applied while maintaining high ejection properties even when using an inkjet method, so that a coating film can be uniformly formed on a large-area substrate.
  • the thickness of the coating film of the sealant may be, for example, 1 ⁇ m or more, and preferably 3 ⁇ m or more. This makes it easier to form a sealing material having sufficient sealing ability. Further, the thickness of the coating film of the sealant may be, for example, 10 ⁇ m or less, and preferably 9 ⁇ m or less. This is expected to reduce the size of organic EL display devices and reduce manufacturing costs. That is, the thickness of the coating film of the sealant may be, for example, 1 to 10 ⁇ m, 1 to 9 ⁇ m, 3 to 10 ⁇ m, or 3 to 9 ⁇ m.
  • the present invention is not limited to the above embodiments.
  • the present invention can adopt various configurations other than those described above.
  • the present invention may be modified or improved from the above embodiments within the scope that can achieve the object of the present invention.
  • the present invention may relate to an organic EL display device that includes an organic EL element and a sealing material that seals the organic EL element.
  • the sealant includes a cured product of the above-mentioned sealant.
  • the organic EL element may be a known organic EL element.
  • the configuration other than the organic EL element and the sealing material may be the same as that of a known organic EL display device.
  • A) Radical polymerizable compound (A-1) SR262 (1,12-dodecanediol dimethacrylate, manufactured by Arkema) (chain monomer) (A-2) BPE200 (ethoxylated bisphenol A dimethacrylate (compound represented by the following formula (m+n 4), manufactured by Shin Nakamura Chemical Industry Co., Ltd.) (aromatic monomer) (A-3) LINC-162A (2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9-hexadecafluoro-1,10-de Candiacrylate, manufactured by Kyoeisha Chemical Co., Ltd.) (fluorine-containing monomer) (A-4) FA-512AS (dicyclopentenyloxyethyl acrylate, manufactured by Showa Denko Materials) (unsaturated alicyclic monomer) (A-5) DCP (dimethylol-tricyclode
  • B Polymerization initiator (B-1) TPO (2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide, manufactured by IGM Resins)
  • C Stable radical type compound (C-1) TEMPO methacrylate (4-methacryloyloxy-2,2,6,6-tetramethylpiperidine 1-oxyl, manufactured by Tokyo Kasei Kogyo Co., Ltd.)
  • ITO 150nm Hole injection layer (polymer HIL): 60nm Hole transport layer ( ⁇ -NPD): 30nm Light-emitting layer (Ir(ppy) 3 +CBP [6%]): 30 nm Hole blocking layer (BAlq): 10nm Electron transport layer (Alq 3 ): 30 nm Electron injection layer (LiF): 0.8nm Cathode (MgAg/IZO): 10nm/100nm ITO is indium tin oxide, HIL is Hole Injection Layer, ⁇ -NPD is N,N'-diphenyl-N,N'-dinaphthylbenzidine, and Ir(ppy) 3 is an iridium complex [tris(2 -phenylpyridine)iridium], CBP is 4,4'-N,N'-dicarbazole-biphenyl, and BAlq is bis(2-methyl-8-quinolinolato)(p-phenyl, ⁇
  • Alq 3 is tris(8-hydroxyquinolinolato)aluminum
  • LiF is lithium fluoride
  • IZO is indium zinc oxide.
  • a cured film was thus obtained.
  • a mask (cover) having an opening of 10 mm x 10 mm was placed so as to cover the entire cured film, and a SiN film was formed by plasma CVD.
  • the thickness of the formed SiN (inorganic film) was about 1 ⁇ m.
  • a sealed body of an organic EL element was obtained.
  • the obtained sealed body was bonded to a 30 mm x 30 mm x 0.7 mm thick alkali-free glass (Eagle XG manufactured by Corning) using a 30 mm x 30 mm x 25 ⁇ m thick transparent base material-less double-sided tape. In this way, an organic EL display device for evaluation was manufactured.
  • the organic EL display device for evaluation was left standing in a high temperature and high humidity environment of 85° C. and 85% RH for 500 hours. Before and after this high-temperature, high-humidity treatment, a current was applied to the organic EL display device for evaluation, and the light-emitting surface was photographed. The photographed images (images before high-temperature, high-humidity treatment and images after high-temperature, high-humidity treatment) were analyzed using Innotek's image analysis software "Quick Grain" to determine the luminescent area. Then, the luminescent area reduction rate (%) before and after the high temperature and high humidity treatment was calculated.
  • Examples 1-2 Comparative Example 1
  • the radically polymerizable compounds shown in Table 1 were mixed in the composition shown in Table 1, and deaeration treatment was performed in an environment of 60° C. and 800 Pa for the time shown in Table 1.
  • each component was mixed with the composition shown in Table 1 to create a sealant.
  • the above measurements and evaluations were performed on the obtained sealant. The results are shown in Table 1.
  • Examples 3-4 Comparative Example 2
  • the radical polymerizable compounds shown in Table 2 were mixed in the composition shown in Table 2, and deaeration treatment was performed in an environment of 60° C. and 800 Pa for the time shown in Table 2.
  • each component was mixed with the composition shown in Table 2 to create a sealant.
  • the above measurements and evaluations were performed on the obtained sealant. The results are shown in Table 2.

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Abstract

L'invention concerne un agent d'étanchéité pour éléments électroluminescents organiques, qui comprend un composé polymérisable par voie radicalaire, un initiateur de photopolymérisation et un composé de type à radical persistant ayant un radical persistant, et qui présente un indice d'acide de 0,01 à 0,15 (mgKOH/g).
PCT/JP2023/010936 2022-03-25 2023-03-20 Agent d'étanchéité et matériau d'étanchéité pour éléments électroluminescents organiques, dispositif d'affichage électroluminescent organique et procédé de production d'agent d'étanchéité pour éléments électroluminescents organiques WO2023182283A1 (fr)

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Citations (5)

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JP2010044870A (ja) * 2008-08-08 2010-02-25 Nippon Shokubai Co Ltd フラットパネルディスプレイ用封着層形成材料、フラットパネルディスプレイ用封着層、及び、フラットパネルディスプレイ
US20120059143A1 (en) * 2010-09-07 2012-03-08 Basf Se Preparing polyester alcohols
JP2013213182A (ja) * 2011-10-07 2013-10-17 Fujifilm Corp 半導体発光装置用封止剤、これを用いた半導体発光装置用封止材及び半導体発光装置
JP2014127266A (ja) * 2012-12-25 2014-07-07 Furukawa Electric Co Ltd:The 有機エレクトロルミネッセンス素子封止用透明樹脂組成物、有機エレクトロルミネッセンス素子封止用樹脂シート、及び画像表示装置
JP2014182905A (ja) * 2013-03-19 2014-09-29 Furukawa Electric Co Ltd:The 有機エレクトロルミネッセンス素子封止用透明樹脂組成物、有機エレクトロルミネッセンス素子封止用樹脂シート、及び画像表示装置

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2010044870A (ja) * 2008-08-08 2010-02-25 Nippon Shokubai Co Ltd フラットパネルディスプレイ用封着層形成材料、フラットパネルディスプレイ用封着層、及び、フラットパネルディスプレイ
US20120059143A1 (en) * 2010-09-07 2012-03-08 Basf Se Preparing polyester alcohols
JP2013213182A (ja) * 2011-10-07 2013-10-17 Fujifilm Corp 半導体発光装置用封止剤、これを用いた半導体発光装置用封止材及び半導体発光装置
JP2014127266A (ja) * 2012-12-25 2014-07-07 Furukawa Electric Co Ltd:The 有機エレクトロルミネッセンス素子封止用透明樹脂組成物、有機エレクトロルミネッセンス素子封止用樹脂シート、及び画像表示装置
JP2014182905A (ja) * 2013-03-19 2014-09-29 Furukawa Electric Co Ltd:The 有機エレクトロルミネッセンス素子封止用透明樹脂組成物、有機エレクトロルミネッセンス素子封止用樹脂シート、及び画像表示装置

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