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WO2024204248A1 - Composition durcissable, agent de scellement, agent de scellement de cadre, panneau d'affichage, et procédé de fabrication associé - Google Patents

Composition durcissable, agent de scellement, agent de scellement de cadre, panneau d'affichage, et procédé de fabrication associé Download PDF

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Publication number
WO2024204248A1
WO2024204248A1 PCT/JP2024/012039 JP2024012039W WO2024204248A1 WO 2024204248 A1 WO2024204248 A1 WO 2024204248A1 JP 2024012039 W JP2024012039 W JP 2024012039W WO 2024204248 A1 WO2024204248 A1 WO 2024204248A1
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Prior art keywords
sealant
curable composition
mass
parts
tertiary amine
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PCT/JP2024/012039
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English (en)
Japanese (ja)
Inventor
桂 永田
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Mitsui Chemicals Inc
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Mitsui Chemicals Inc
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Priority to CN202480019637.7A priority Critical patent/CN120813624A/zh
Priority to JP2025510960A priority patent/JPWO2024204248A1/ja
Publication of WO2024204248A1 publication Critical patent/WO2024204248A1/fr
Anticipated expiration legal-status Critical
Pending legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
    • C08K3/013—Fillers, pigments or reinforcing additives
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/17—Amines; Quaternary ammonium compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
    • C08K5/3432—Six-membered rings
    • C08K5/3435—Piperidines
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/02—Details
    • H05B33/04—Sealing arrangements, e.g. against humidity
    • H—ELECTRICITY
    • 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

Definitions

  • the present invention relates to a curable composition, a sealant, a frame sealant, a display panel, and a method for manufacturing the same.
  • organic EL elements organic electroluminescence elements
  • display elements are generally susceptible to deterioration due to moisture and oxygen in the air. For this reason, in various display devices, the display elements are generally sealed with a sealing layer.
  • an organic EL display panel has an element substrate having an organic EL element, an opposing substrate, and a sealing layer disposed between them to seal the organic EL element.
  • Such organic EL display panels are manufactured by various methods.
  • the dam-fill method is known as one such manufacturing method.
  • an organic EL display panel is manufactured through, for example, the steps of 1) applying a first sealant in a frame shape onto an opposing substrate, 2) filling the area surrounded by the first sealant with a second sealant to form a sealant layer, 3) irradiating the sealant layer with light, 4) bonding a substrate on which an organic EL element is disposed to the opposing substrate having the sealant layer after light irradiation, and 5) heating and curing the sealant layer (see, for example, Patent Document 1).
  • a frame sealant used in the above-mentioned method for example, a sealant containing a polyolefin, an epoxy compound (curable resin A), a heat curing agent, and a water-absorbent filler is known (see, for example, Patent Document 2).
  • a thermal cationic initiator is used as the heat curing agent.
  • sealant for organic EL elements is a sealant that contains a photocurable compound containing a (meth)acrylic-modified epoxy resin and a photocationic polymerization initiator (see, for example, Patent Document 3).
  • the sealant shown in Patent Document 2 is cured by heating at 100°C, which poses the problem that the element is easily damaged by heat. To prevent such damage, the sealant is required to have low-temperature curing properties.
  • the above-mentioned sealant is required to have a predetermined pot life or more after light irradiation, that is, to maintain a moderately low viscosity after light irradiation.
  • the sealant applied to one substrate is irradiated with light to cause provisional curing, and then the other substrate is bonded to the sealant and heated to cause full curing.
  • the sealant shown in Patent Documents 2 and 3 is prone to excessive viscosity increase because the curing reaction proceeds too much after light irradiation and before the other substrate is bonded. Therefore, there is a problem that the fluidity and tack of the sealant are easily impaired during bonding, making it difficult to obtain sufficient adhesive strength.
  • the higher the low-temperature curing property the easier it is for the viscosity to increase after light irradiation, so it is desirable to achieve a good balance between these two.
  • the frame sealant that seals the periphery of the element contains a filler from the viewpoint of reducing the moisture permeability of the cured product and improving shape retention.
  • Such sealants have a greater increase in viscosity after light irradiation, and are more likely to lose their fluidity and tack during lamination. For this reason, it is even more important to keep the viscosity low after light irradiation.
  • the present invention was made in consideration of the above circumstances, and provides a curable composition, a sealant, a frame sealant, a display panel, and a method for manufacturing the same, which combine low-temperature curing properties with viscosity stability after light irradiation and can provide a cured product with low moisture permeability and high adhesive strength.
  • a curable composition comprising a curable compound, a photocationic polymerization initiator, a tertiary amine, and an inorganic filler, wherein the content of the tertiary amine is 20 parts by mass or more per 100 parts by mass of the photocationic polymerization initiator.
  • the content of the inorganic filler is 20 parts by mass or more and 400 parts by mass or less with respect to 100 parts by mass of the curable compound.
  • a display panel comprising: an element substrate on which elements are arranged; a counter substrate arranged opposite the element substrate with the elements interposed therebetween; and a sealing portion arranged between the element substrate and the counter substrate for sealing the elements, the sealing portion including a cured product of the sealant according to [9].
  • a method for manufacturing a display panel comprising: a step of applying a first sealant in a frame shape along an outer periphery of a display area on one surface of an element substrate or an opposing substrate; a step of filling a second sealant into the area surrounded by the first sealant to form a sealant layer; a step of irradiating the sealant layer with light; a step of bonding one substrate and the other substrate together via the sealant layer irradiated with light; and a step of heating and curing the sealant layer, wherein at least one of the first sealant and the second sealant is the sealant described in [9].
  • the method for manufacturing a display panel according to [12] wherein the first sealant is the sealant according to [9].
  • the present invention was made in consideration of the above circumstances, and provides a curable composition, a sealant, a frame sealant, a display panel, and a method for manufacturing the same, which combine low-temperature curing properties with viscosity stability after light irradiation and can provide a cured product with low moisture permeability and high adhesive strength.
  • curable compositions with low-temperature curing properties tend to increase in viscosity after exposure to light and are unable to maintain a low viscosity.
  • the curable composition of the present invention contains a curable compound, a photocationic polymerization initiator, a tertiary amine, and an inorganic filler.
  • the content of the tertiary amine in the curable composition of the present invention is a predetermined amount or more relative to the photocationic polymerization initiator.
  • the curable composition When the curable composition is first irradiated with light, an acid is generated from the photocationic polymerization initiator. This acid is captured by a sufficient amount of tertiary amine. Therefore, the curing of the curable compound does not proceed easily at the time of light irradiation, and the viscosity of the curable composition after light irradiation is kept low.
  • the curable composition is then heated at a low temperature, the acid trapped by the tertiary amine is released and the curable compound is cured. Therefore, the curable composition has excellent low-temperature curing properties.
  • the curable composition when used for sealing an optical element in, for example, a display panel including the optical element, the optical element can be sealed with low moisture permeability and high adhesive strength while suppressing damage to the optical element due to heat.
  • the curable composition according to one embodiment of the present invention will be specifically described.
  • Curable Composition contains a curable compound, a photocationic polymerization initiator, a tertiary amine, and an inorganic filler.
  • the curable compound includes a curable compound that is polymerized and cured by active species generated from a photocationic polymerization initiator.
  • examples of such a curable compound include an epoxy compound and an oxetane compound, and from the viewpoint of enhancing thermosetting properties, it is preferable to include an epoxy compound.
  • the curable compound may include only one type of epoxy compound, or may include two or more types.
  • an epoxy compound refers to a compound having one or more epoxy groups in the molecule.
  • the number of epoxy groups contained in one molecule of an epoxy compound may be one or may be two or more. From the viewpoint of increasing the curing reactivity, it is preferable that the number of epoxy groups contained in one molecule of an epoxy compound is two or more.
  • epoxy compounds include known epoxy compounds, such as aromatic epoxy compounds, aliphatic epoxy compounds, and alicyclic epoxy compounds. Among these, from the viewpoint of further reducing the moisture permeability of the cured product, it is preferable that at least one of the epoxy compounds contains an aromatic epoxy compound.
  • aromatic epoxy compound examples include glycidyl ethers of alcohols (including polyhydric alcohols) containing an aromatic ring.
  • bisphenol-type glycidyl ether compounds obtained by reacting epichlorohydrin with bisphenols such as bisphenol A, bisphenol S, bisphenol F, bisphenol AD, etc., or diols obtained by modifying these aromatic diols with ethylene glycol, propylene glycol, alkylene glycol, etc.
  • trisphenol type glycidyl ether compounds obtained by reacting a trisphenol compound (e.g., 1,1,1-tris(hydroxyphenyl)methane, 1-[ ⁇ -methyl- ⁇ -(4-hydroxyphenyl)ethyl]-3-[ ⁇ , ⁇ -bis(4-hydroxyphenyl)ethyl]benzene (or 4-[4-[1,1-bis(4-hydroxyphenyl)ethyl]- ⁇ , ⁇ -dimethylbenzyl]phenol) with epichlorohydrin
  • bisphenol type epoxy compounds such as bisphenol A type epoxy compounds and bisphenol F type epoxy compounds, cresol novolac type epoxy compounds, phenol novolac type epoxy compounds, triphenol methane type epoxy compounds, triphenol ethane type epoxy compounds, trisphenol type epoxy compounds, dicyclopentadiene type epoxy compounds, diphenyl ether type epoxy compounds, and biphenyl type epoxy compounds are preferred.
  • the epoxy compound may be liquid or solid. From the viewpoint of improving the coatability of the curable composition, a liquid epoxy compound is preferred. From the viewpoint of reducing the moisture permeability of the cured product, a solid epoxy compound is preferred.
  • the softening point of the solid epoxy compound is preferably 40°C or higher and 150°C or lower. The softening point can be measured by the ring and ball method specified in JIS K7234.
  • the weight-average molecular weight of the epoxy compound is preferably 200 or more and 10,000 or less, and more preferably 300 or more and 5,000 or less.
  • the weight-average molecular weight of the epoxy compound is measured in terms of polystyrene by gel permeation chromatography (GPC).
  • the curable compound may contain only one type of epoxy compound, or may contain two or more types.
  • a liquid epoxy compound may be combined with a solid epoxy compound.
  • a bifunctional aromatic epoxy compound may be combined with a trifunctional or higher aromatic epoxy compound.
  • the trifunctional or higher aromatic epoxy compound when a difunctional aromatic epoxy compound is combined with a trifunctional or higher aromatic epoxy compound, the trifunctional or higher aromatic epoxy compound can be, for example, 10% by mass or more, preferably 30% by mass or more and 70% by mass or less, based on the total amount of epoxy compounds.
  • the content of the trifunctional or higher aromatic epoxy compound is 10% by mass or more, the moisture permeability of the cured product can be further increased.
  • the viscosity of the curable composition after light irradiation is likely to increase, the acid generated from the photocationic polymerization initiator is trapped by the tertiary amine, so that excessive viscosity increase can be suppressed.
  • the curable compound may also contain both an epoxy compound and an oxetane compound.
  • the content of the epoxy compound is preferably 30% by mass or more, more preferably 50% by mass or more, and may be 100% by mass, based on the curable compound. If the amount of the epoxy compound is 30% by mass or more, it is easier to increase the curing reactivity by heating.
  • the total amount of the curable compounds is preferably 20% by mass or more and 90% by mass or less, and more preferably 30% by mass or more and 70% by mass or less, relative to the curable composition.
  • amount of the curable compounds is 20% by mass or more, it is easier to obtain curing reactivity and to increase the adhesive strength of the cured product.
  • amount of the curable compounds is 90% by mass or less, for example, the amount of inorganic filler becomes relatively large, and it is easier to increase the shape retention of the resulting sealant.
  • the photocationic polymerization initiator is, for example, a photoacid generator that generates an acid upon irradiation with light.
  • the absorption wavelength of the photocationic polymerization initiator is not particularly limited, but it is preferable for it to absorb light with a wavelength of 360 nm or more, and it is more preferable for it to absorb light with a wavelength of 360 nm or more and 430 nm or less. If the absorption wavelength of the photocationic polymerization initiator is within the above range, it is possible to reduce the effect on optical elements, for example.
  • the photocationic polymerization initiator is not particularly limited, and any known photocationic polymerization initiator can be used.
  • photocationic polymerization initiator examples include aromatic sulfonium salts, aromatic iodonium salts, aromatic diazonium salts, aromatic ammonium salts, and the like, whose anion portion is BF 4 ⁇ , (Rf) n PF 6 -n ⁇ (Rf is an organic group, n is an integer of 1 to 5), PF 6 ⁇ , SbF 6 ⁇ , or BX 4 ⁇ (X is a phenyl group substituted with at least two or more fluorine or trifluoromethyl groups).
  • aromatic sulfonium salts include bis[4-(diphenylsulfonio)phenyl]sulfide bishexafluorophosphate, bis[4-(diphenylsulfonio)phenyl]sulfide bishexafluoroantimonate, bis[4-(diphenylsulfonio)phenyl]sulfide bistetrafluoroborate, bis[4-(diphenylsulfonio)phenyl]sulfide tetrakis(pentafluorophenyl)borate, diphenyl-4-(phenylthio)phenylsulfonium hexafluorophosphate, diphenyl-4-(phenylthio)phenylsulfonium hexafluoroantimonate, diphenyl-4-(phenylthio)phenylsulfonium tetrafluoroborate, etc.
  • aromatic iodonium salts include diphenyliodonium hexafluorophosphate, diphenyliodonium hexafluoroantimonate, diphenyliodonium tetrafluoroborate, diphenyliodonium tetrakis(pentafluorophenyl)borate, bis(dodecylphenyl)iodonium hexafluorophosphate, bis(dodecylphenyl)iodonium hexafluoroantimonate, bis(dodecylphenyl)iodonium tetrafluoroborate, bis(dodecylphenyl)iodonium tetrakis(pentafluorophenyl)borate, etc.
  • aromatic diazonium salts include phenyldiazonium hexafluorophosphate, phenyldiazonium hexafluoroantimonate, phenyldiazonium tetrafluoroborate, phenyldiazonium tetrakis(pentafluorophenyl)borate, etc.
  • aromatic ammonium salts examples include 1-benzyl-2-cyanopyridinium hexafluorophosphate, 1-benzyl-2-cyanopyridinium hexafluoroantimonate, etc.
  • photocationic polymerization initiators examples include Irgacure 250, Irgacure 270, Irgacure 290 (manufactured by BASF), CPI-100P, CPI-101A, CPI-200K, CPI-210S, CPI-310B, CPI-400PG (manufactured by San-Apro), SP-150, SP-170, SP-171, SP-056, SP-066, SP-130, SP-140, SP-601, SP-606, SP-701 (manufactured by ADEKA).
  • sulfonium salts such as Irgacure 270, Irgacure 290, CPI-100P, CPI-101A, CPI-200K, CPI-210S, CPI-310B, CPI-400PG, SP-150, SP-170, SP-171, SP-056, SP-066, SP-601, SP-606, and SP-701 are preferred.
  • the cationic photopolymerization initiator may be of one type or of two or more types in combination.
  • the content of the cationic photopolymerization initiator is preferably 0.1 to 20 parts by mass, more preferably 0.5 to 15 parts by mass, and even more preferably 0.8 to 8 parts by mass, relative to 100 parts by mass of the curable compound. If the content of the cationic photopolymerization initiator is 0.1 parts by mass or more, more acid is likely to be generated by light irradiation, making it easier for the curing reaction to occur when curing by heating. If the content of the cationic photopolymerization initiator is 20 parts by mass or less, bleed-out can be reduced, making it possible to reduce contamination of optical elements, etc.
  • Tertiary amines capture the acid generated from the photocationic polymerization initiator upon light irradiation, thereby making it difficult for the curing reaction of the curable compound to occur upon light irradiation, and can suppress an excessive increase in the viscosity of the curable composition after light irradiation.
  • Tertiary amines include monofunctional tertiary amines having one amino group in the molecule, bifunctional tertiary amines having two amino groups, and trifunctional or higher tertiary amines having three or more amino groups.
  • bifunctional tertiary amines and trifunctional or higher tertiary amines are preferred from the viewpoint of further increasing the acid trapping efficiency, and bifunctional tertiary amines are more preferred from the viewpoint of easier maintenance of compatibility with epoxy compounds.
  • the tertiary amine preferably has an N-O bond, from the viewpoint of making it easier to release the trapped acid when heated and further improving low-temperature curing properties.
  • a bifunctional tertiary amine having an N-O bond is preferred.
  • the tertiary amine has a hindered structure, from the viewpoint of making it easier to release the trapped acid when heated and further improving low-temperature curing properties.
  • hindered structures include structures with steric hindrance, such as 2,2,6,6-tetramethylpiperidine.
  • the tertiary amine is preferably a bifunctional tertiary amine having an N-O bond, more preferably a bifunctional tertiary amine having an N-O bond and a hindered structure, and even more preferably a tertiary amine having an N-O bond and two 2,2,6,6-tetramethylpiperidine structures in the molecule.
  • Such tertiary amines include compounds represented by formula (1) or (2).
  • R 3 represents an alkyl group having 1 to 20 carbon atoms.
  • Examples of linear or branched alkyl groups having 1 to 20 carbon atoms include butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, and eicosyl groups.
  • Two R 3s may be the same or different.
  • R 4 represents a linear or branched alkyl group having 1 to 20 carbon atoms.
  • linear or branched alkyl groups having 4 to 20 carbon atoms include a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, and an eicosyl group.
  • Two R 4s may be the same or different from each other.
  • R5 represents an alkylene group having 1 to 8 carbon atoms.
  • alkylene group having 1 to 8 carbon atoms include a methylene group, an ethylene group, a propylene group, a butylene group, a pentylene group, a hexylene group, a heptylene group, and an octylene group.
  • Examples of the compound represented by formula (1) include a compound represented by formula (1-1); examples of the compound represented by formula (2) include a compound represented by formula (2-1).
  • tertiary amines can also be used.
  • examples of commercially available tertiary amines include Adeka STAB LA-81 (manufactured by ADEKA CORPORATION) and Tinuvin 123 (manufactured by BASF Japan).
  • the tertiary amine may contain only one type, or may contain two or more types.
  • the content of the tertiary amine is preferably 20 parts by mass or more per 100 parts by mass of the photocationic polymerization initiator from the viewpoint of capturing the acid generated from the photocationic polymerization initiator. If the content of the tertiary amine is 20 parts by mass or more, a large amount of acid can be trapped, so that the increase in viscosity after light irradiation can be more easily suppressed and tackiness can be more increased. From the same viewpoint, the content of the tertiary amine is preferably 60 parts by mass or more, and more preferably 65 parts by mass or more, per 100 parts by mass of the photocationic polymerization initiator.
  • the upper limit of the content of the tertiary amine is not particularly limited, but it may be, for example, 100 parts by mass or less from the viewpoint of further reducing the amount of tertiary amine remaining as an unreacted component after curing, further reducing the decrease in adhesion and moisture permeability of the cured product, and improving the physical properties of the cured product.
  • the content of the tertiary amine is preferably, for example, 0.5 parts by mass or more and 20 parts by mass or less, and more preferably 1 part by mass or more and 5 parts by mass or less, relative to 100 parts by mass of the curable compound. If the content of the tertiary amine is 0.5 parts by mass or more, a larger amount of acid can be trapped, making it easier to suppress an increase in viscosity after light irradiation and further increasing tack. If the content of the tertiary amine is 20 parts by mass or less, the amount of tertiary amine remaining unreacted after heat curing can be reduced, making it possible to further suppress a decrease in the physical properties of the cured product.
  • the inorganic filler can have the function of increasing the shape retention of the curable composition and reducing the moisture permeability of the cured product.
  • inorganic fillers include calcium carbonate, magnesium carbonate, barium sulfate, magnesium sulfate, aluminum silicate, zirconium silicate, iron oxide, titanium oxide, titanium nitride, alumina other than the above, zinc oxide, silicon dioxide (silica), potassium titanate, kaolin, talc, glass beads, sericite activated clay, bentonite, aluminum nitride, and silicon nitride. Of these, silicon dioxide and talc are preferred.
  • the inorganic filler may have a regular shape such as a sphere, plate, or needle, or may have an irregular shape.
  • the average primary particle diameter of the inorganic filler is preferably 0.1 ⁇ m or more and 5 ⁇ m or less, and more preferably 0.5 ⁇ m or more and 3 ⁇ m or less, from the viewpoint of, for example, the shape retention of the cured product after lamination, thickness adjustment, and reduction of moisture permeability. If the average primary particle diameter of the inorganic filler is 5 ⁇ m or less, it is easier to reduce unevenness in the thickness of the cured product after lamination, and if it is 0.1 ⁇ m or more, it is possible to further suppress the increase in viscosity.
  • the average primary particle diameter of the inorganic filler is in a range smaller than 0.1 ⁇ m, for example, 7 nm or more and less than 100 nm.
  • the average primary particle diameter of the inorganic filler can be measured by the laser diffraction method described in JIS Z8825 (2013).
  • the specific surface area of the inorganic filler is preferably 0.5 m 2 /g or more and 20 m 2 /g or less.
  • the specific surface area of the inorganic filler is measured by the BET method described in JIS Z8830 (2013).
  • the curable composition may contain only one type of inorganic filler, or may contain two or more types. From the viewpoint of adjusting the viscosity (thixotropy) and the shape retention and thickness of the cured product, for example, the curable composition may contain an inorganic filler having a relatively small average primary particle diameter (e.g., less than 0.1 ⁇ m) and an inorganic filler having a relatively large average primary particle diameter (e.g., 0.1 ⁇ m or more). It is preferable that the content of the inorganic filler having a relatively small average particle diameter is less than the content of the inorganic filler having a relatively large average particle diameter.
  • the content of the inorganic filler is preferably 10 parts by mass or more and 350 parts by mass or less, relative to 100 parts by mass of the curable compound.
  • the content of the inorganic filler is 10 parts by mass or more, it is easier to improve the shape retention of the cured product and to reduce moisture permeability.
  • the content of the inorganic filler is 350 parts by mass or less, not only is the applicability of the curable composition less likely to be impaired, but also a decrease in adhesive strength due to a decrease in the relative amount of the curable compound or a loss in flexibility of the cured product can be more suppressed. From the same viewpoint, it is more preferable that the content of the inorganic filler is 150 parts by mass or more and 300 parts by mass or less.
  • the curable composition may further contain other components in addition to the above-mentioned components.
  • the other components include a photosensitizer, a silane coupling agent, a tackifier, organic fine particles, a plasticizer, an antioxidant, and an antifoaming agent.
  • Photosensitizer has the function of further improving the polymerization initiation efficiency of the above-mentioned cationic photopolymerization initiator and further accelerating the curing reaction of the curable compound.
  • photosensitizers include thioxanthone compounds such as 2,4-diethylthioxanthone, 2,2-dimethoxy-1,2-diphenylethan-1-one, benzophenone, 2,4-dichlorobenzophenone, methyl o-benzoylbenzoate, 4,4'-bis(dimethylamino)benzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, 9,10-dibutoxyanthracene, etc.
  • the curable composition may contain only one type of photosensitizer, or may contain two or more types.
  • the content of the photosensitizer is, for example, preferably 0.1 parts by mass or more and 5 parts by mass or less, and more preferably 0.5 parts by mass or more and 2 parts by mass or less, relative to 100 parts by mass of the curable compound.
  • the curable composition may contain only one type of photosensitizer, or may contain two or more types.
  • silane Coupling Agents examples include vinyltrimethoxysilane, ⁇ -(meth)acryloxypropyltrimethoxysilane, ⁇ -glycidoxypropyltrimethoxysilane, and ⁇ -glycidoxypropyltriethoxysilane.
  • the content of the silane coupling agent is preferably 0.1 parts by mass or more and 10 parts by mass or less, and more preferably 1.0 parts by mass or more and 5.0 parts by mass or less, relative to 100 parts by mass of the curable compound. If the content of the silane coupling agent is 0.1 parts by mass or more, it is easier to increase the adhesive strength of the cured product, and if it is 10 parts by mass or less, it is possible to further reduce the decrease in moisture permeability resistance of the cured product.
  • the total amount of the other components is preferably 0.1% by mass or more and 50% by mass or less based on the total amount of the curable composition. When the total amount is 50% by mass or less, the viscosity of the curable composition is unlikely to increase excessively, and the coatability is unlikely to be impaired.
  • the viscosity of the curable composition measured using an E-type viscometer at 25°C and 2.5 revolutions per minute is preferably, for example, 50 Pa ⁇ s or more and 400 Pa ⁇ s or less, and more preferably 100 Pa ⁇ s or more and 300 Pa ⁇ s or less.
  • the viscosity of the curable composition is 50 Pa ⁇ s or more, the composition has a moderately high viscosity, and therefore the shape retention during application is more likely to be improved.
  • the viscosity of the curable composition is 400 Pa ⁇ s or less, the application property during application by a dispenser is less likely to be impaired.
  • the viscosity at 25° C. after 60 seconds is preferably 1.0 ⁇ 10 4 Pa ⁇ s or less, more preferably 1.0 ⁇ 10 2 Pa ⁇ s or more and 5.0 ⁇ 10 3 Pa ⁇ s or less.
  • the viscosity of the curable composition is 1.0 ⁇ 10 4 Pa ⁇ s or less, the composition has tack even after light irradiation, and the fluidity during lamination is less likely to be impaired, and the adhesive strength of the cured product can be increased.
  • the viscosity of the curable composition is 1.0 ⁇ 10 2 Pa ⁇ s or more, the curable composition after light irradiation can further have shape retention.
  • the viscosity after light irradiation is also measured using an E-type viscometer at 25°C and 2.5 revolutions per minute. Specifically, a coating film of the curable composition having a thickness of 10 ⁇ m is formed on a 0.7 mm-thick alkali-free glass using a bar coater No. 6. The coating film is left at room temperature (25°C) for 3 minutes while purging with nitrogen.
  • the coating film is irradiated with ultraviolet light from a metal halide lamp having a wavelength of 365 nm at a UV illuminance of 100 mW/ cm2 and an integrated light quantity of 3000 mJ/ cm2 , and then the coating film is scraped off and the viscosity after 60 seconds is measured in the same manner as above.
  • the viscosity of the curable composition after light irradiation can be adjusted by the content of tertiary amine and the content of inorganic filler. For example, if the amount of tertiary amine is large relative to the amount of cationic photopolymerization initiator, more acid generated from the cationic photopolymerization initiator upon light irradiation can be trapped, making it easier to reduce the increase in viscosity of the curable composition after light irradiation. On the other hand, the higher the content of inorganic filler, the greater the increase in viscosity after light irradiation is likely to be.
  • the curable composition according to the present embodiment can be used as a sealant since the viscosity of the curable composition according to the present embodiment can be adjusted to a suitable level for bonding after irradiation with light. That is, the sealant contains the curable composition.
  • the sealant can be used as a sealant or adhesive for various elements such as organic EL elements, LED elements, liquid crystal elements, semiconductor elements, solar cell elements, etc.
  • the sealant may be a sealant for sealing light-emitting elements such as organic EL elements and micro LED elements.
  • the sealant may be a surface sealant or a frame sealant. Frame sealants are required to have a high degree of shape retention when cured, and therefore the curable composition is particularly suitable as a frame sealant.
  • a display panel according to one embodiment of the present invention has an element substrate, a counter substrate, and a sealing portion disposed between them for sealing the elements.
  • the element substrate has a substrate and an element.
  • the substrate is a transparent substrate.
  • the material of the transparent substrate may be an inorganic material such as glass, or may be a plastic such as polycarbonate, polyethylene terephthalate, polyethersulfone, and PMMA.
  • the element may be various elements such as an organic EL element, an LED element (including micro LED), a liquid crystal element, a semiconductor element, and a solar cell element.
  • the organic EL element is disposed on the substrate and has a laminated structure of an anode/light-emitting layer/negative electrode.
  • the opposing substrate is disposed so as to face the element substrate via the element.
  • the opposing substrate may be a transparent substrate similar to that described above.
  • the opposing substrate may have, for example, a color filter layer.
  • the sealing portion includes a frame-shaped first sealing portion arranged to surround the outer periphery of the element, and a second sealing portion filled in the area surrounded by the first sealing portion.
  • the first sealing portion is a hardened product of the first sealant (dam material).
  • the second sealing portion is a hardened product of the second sealant (fill material).
  • At least one of the first sealant and the second sealant, preferably the first sealant, is the above-mentioned curable composition.
  • the display panel can be manufactured by any method.
  • the display panel can be manufactured by 1) applying a first sealant in a frame shape on one of the opposing substrate and the element substrate so as to surround a display region; 2) filling a region surrounded by the first sealant applied in a frame shape with a second sealant to form a sealant layer; 3) irradiating the sealant layer with light; 4) bonding one substrate to another substrate via the sealant layer irradiated with light; 5) a step of heating and curing the sealant layer.
  • step 1) the first sealant is applied in a frame shape surrounding the display area on one of the opposing substrate and the element substrate, for example, on the opposing substrate.
  • application method can be done, for example, with a dispenser or the like.
  • step 2 the area surrounded by the frame-shaped application of the first sealant is filled with the second sealant to form a sealant layer.
  • the sealant layer is irradiated with light.
  • the type of light to be irradiated is appropriately selected depending on the type of cationic photopolymerization initiator in the curable composition, which is the first sealant, but light in the visible light region is preferred, for example light with a wavelength of 370 nm or more and 450 nm or less. This is because light in this range of wavelengths causes relatively little damage to the drive electrode.
  • a known light source that emits ultraviolet or visible light can be used, for example a metal halide lamp.
  • the amount of light irradiation is preferably such that a suitable amount of tack remains in the curable composition after irradiation.
  • the amount of light irradiation may be from 1000 mJ/ cm2 to 10,000 mJ/ cm2 with an intensity of from 10 mW/ cm2 to 1,000 mW/ cm2 .
  • the light irradiation starts the hardening of the first sealant and the second sealant. After the light irradiation is finished, the temperature of the substrate may rise to about 35°C, and the substrate may wait in this state. In this way, by waiting for a predetermined time after the light irradiation, rather than bonding the substrates immediately, the hardening of the first sealant and the second sealant progresses appropriately, and the viscosity of the substrate increases.
  • step 4 when the viscosity of the first sealant and the second sealant has increased to an appropriate level, the opposing substrate and the element substrate are bonded together via the sealant layer.
  • the bonding is performed by pressing the element substrate and the opposing substrate with a press or the like in a vacuum chamber so as to crush the sealant layer.
  • the first sealant which has a relatively high viscosity, is present in a frame shape around the second sealant, preventing the second sealant from leaking out.
  • step 5 the laminate is heated to heat and harden the first and second sealants.
  • the heating temperature may be any temperature at which the sealant layer hardens, and from the viewpoint of minimizing damage to the element due to heat, a low temperature is preferable, for example a temperature lower than 100°C, preferably 40°C or higher and 90°C or lower, and more preferably 60°C or higher and 85°C or lower.
  • the heating time depends on the heating temperature, but is, for example, 60 minutes or longer and 120 minutes or shorter.
  • step 3 when light is irradiated, acid is generated from the photocationic polymerization initiator, but since it is captured by the tertiary amine, the viscosity does not increase excessively and a relatively low viscosity can be maintained. Therefore, even if the curable composition contains an inorganic filler, the fluidity and tack are not easily impaired when bonding in step 4).
  • step 5 the acid captured by the tertiary amine is released by heating, and the curable compound cures at a low temperature. As a result, sufficient adhesive strength can be obtained even with a curable composition that contains an inorganic filler.
  • the curable composition is mainly used as a sealant for organic EL elements, but it can also be used as a sealant or adhesive for various elements such as LED elements (including micro LEDs), liquid crystal elements, semiconductor elements, solar cell elements, and as an interlayer filler for touch panels.
  • the curable composition can also be used as a sealant or adhesive applied to substrates that do not have optical transparency, such as printed circuit boards used in smart antennas for electric vehicles and substrates having a light-shielding portion under wiring used in dye-sensitized solar cells.
  • Curable compound (A) Curable compound (A-1): Aromatic trifunctional epoxy compound (VG3101L, 2-(glycidyloxyphenyl)propylphenyl)-1,1-di(glycidyloxyphenyl)ethane, solid, manufactured by Printec Co., Ltd.
  • Curable compound (A-2) Bisphenol F type epoxy resin (YL983U, bifunctional, liquid, manufactured by Mitsubishi Chemical Corporation)
  • Tertiary amine (C) A compound represented by the following formula (Tinuvin 123 manufactured by BASF Japan Ltd.)
  • Inorganic filler (D) Inorganic filler (D-1): spherical silica (Tokuyama Corporation, Sign Seal SP07M, average particle size 0.7 ⁇ m) Inorganic filler (D-2): fine silica powder (Tokuyama Corporation, HM-30S, average particle size 7 nm)
  • Silane coupling agent (F) ⁇ KBM403 manufactured by Shin-Etsu Chemical Co., Ltd.
  • Curable Composition 100 parts by mass of the curable compound (A-1), 200 parts by mass of the curable compound (A-2), 15 parts by mass of the photocationic polymerization initiator (B), 5 parts by mass of the tertiary amine (C), 500 parts by mass of the inorganic filler (D-1), 20 parts by mass of the inorganic filler (D-2), 5 parts by mass of the photosensitizer (E), and 30 parts by mass of the silane coupling agent (F) were mixed in a roll kneader to obtain a curable composition.
  • Example 2 Comparative Example 1
  • Curable compositions were obtained in the same manner as in Example 1, except that the amounts of each component were changed as shown in Table 1.
  • Viscosity (before and after light irradiation) The viscosity of the obtained curable composition was measured at 25° C. using an E-type viscometer (TVE-35L type viscometer, manufactured by Toki Sangyo Co., Ltd., rotor name: 3° ⁇ R9.7) in accordance with the cone-plate viscometer method of JIS K5600-2-3 (2014). The rotation speed of the cone-plate during the measurement was 2.5 rotations/min.
  • E-type viscometer TVE-35L type viscometer, manufactured by Toki Sangyo Co., Ltd., rotor name: 3° ⁇ R9.7
  • a coating film of the curable composition having a thickness of 10 ⁇ m was formed on a non-alkali glass having a thickness of 0.7 mm using a bar coater No. 6.
  • the coating film was left for 3 minutes at room temperature (25° C.) while purging with nitrogen.
  • the coating film was irradiated with ultraviolet light from a metal halide lamp having a wavelength of 365 nm at a UV illuminance of 100 mW/cm 2 and an integrated light quantity of 3000 mJ/cm 2 , and then the coating film was scraped off, and the viscosity after 60 seconds was measured in the same manner as above.
  • the obtained curable composition was applied in a circular shape on a non-alkali glass of 25 mm x 45 mm x 0.7 mm using a screen plate.
  • the seal pattern was a circle with a diameter of 1 mm.
  • the coating film of the curable composition was irradiated with light having a wavelength of 365 nm at an irradiation intensity of 100 mW/ cm2 for 30 seconds from one side of the non-alkali glass, and then a pair of non-alkali glass of 0.7 mm thickness was bonded to the coating film, and heated in an oven at 80°C for 60 minutes to obtain a laminate sample.
  • the obtained sample was then aged in a thermostatic chamber at 23° C. for 24 hours, and then pulled in a tensile testing machine (Intesco Model 210 tensile testing machine) in a direction parallel to the surface at a speed of 2 mm/min, and the stress at this time was measured.
  • a tensile testing machine Intesco
  • the curable composition of Comparative Example 1 which does not contain a tertiary amine, shows no tack after irradiation with light, and the adhesive strength of the cured product is low.
  • the curable compositions of Examples 1 and 2 which contain a specified amount or more of tertiary amine, are found to retain tack after light irradiation.
  • the adhesive strength of the cured product is also found to be high.
  • curable composition which has both low-temperature curing properties and viscosity stability after light irradiation, and which can give a cured product having low moisture permeability and high adhesive strength.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Optics & Photonics (AREA)
  • Physics & Mathematics (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Pigments, Carbon Blacks, Or Wood Stains (AREA)
  • Sealing Material Composition (AREA)
  • Catalysts (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La composition durcissable de l'invention contient un composé durcissable, un initiateur de polymérisation par voie photocationique, une amine tertiaire et une charge inorganique. La teneur en amine tertiaire est supérieure ou égale à 20 parties en masse pour 100 parties en masse dudit initiateur de polymérisation par voie photocationique.
PCT/JP2024/012039 2023-03-29 2024-03-26 Composition durcissable, agent de scellement, agent de scellement de cadre, panneau d'affichage, et procédé de fabrication associé Pending WO2024204248A1 (fr)

Priority Applications (2)

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CN202480019637.7A CN120813624A (zh) 2023-03-29 2024-03-26 固化性组合物、密封剂、框密封剂、显示面板及其制造方法
JP2025510960A JPWO2024204248A1 (fr) 2023-03-29 2024-03-26

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Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004099775A (ja) * 2002-09-10 2004-04-02 Fuji Photo Film Co Ltd セルロースアシレートフィルム、並びに該フィルムを用いた光学フィルム、液晶表示装置及びハロゲン化銀写真感光材料
JP2004238456A (ja) * 2003-02-05 2004-08-26 Konica Minolta Holdings Inc インク、画像形成方法、印刷物及び記録装置
JP2006160802A (ja) * 2004-12-03 2006-06-22 Mitsubishi Chemicals Corp 耐汚染性付与剤、硬化物および物品
JP2009275080A (ja) * 2008-05-13 2009-11-26 Konica Minolta Ij Technologies Inc 活性エネルギー線硬化性組成物及びインクジェット用インク
WO2012060449A1 (fr) * 2010-11-05 2012-05-10 株式会社日本触媒 Composition de résine durcissable par voie cationique
CN110885619A (zh) * 2019-12-12 2020-03-17 上海华谊精细化工有限公司 一种辐照固化抗污卷材涂料及其制备方法
WO2021006070A1 (fr) * 2019-07-05 2021-01-14 三井化学株式会社 Agent d'étanchéité pour élément d'affichage électroluminescent organique, et dispositif d'affichage électroluminescent organique
WO2023153387A1 (fr) * 2022-02-08 2023-08-17 三井化学株式会社 Composition polymérisable, matériau d'étanchéité, dispositif d'affichage d'image et procédé de fabrication de dispositif d'affichage d'image

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004099775A (ja) * 2002-09-10 2004-04-02 Fuji Photo Film Co Ltd セルロースアシレートフィルム、並びに該フィルムを用いた光学フィルム、液晶表示装置及びハロゲン化銀写真感光材料
JP2004238456A (ja) * 2003-02-05 2004-08-26 Konica Minolta Holdings Inc インク、画像形成方法、印刷物及び記録装置
JP2006160802A (ja) * 2004-12-03 2006-06-22 Mitsubishi Chemicals Corp 耐汚染性付与剤、硬化物および物品
JP2009275080A (ja) * 2008-05-13 2009-11-26 Konica Minolta Ij Technologies Inc 活性エネルギー線硬化性組成物及びインクジェット用インク
WO2012060449A1 (fr) * 2010-11-05 2012-05-10 株式会社日本触媒 Composition de résine durcissable par voie cationique
WO2021006070A1 (fr) * 2019-07-05 2021-01-14 三井化学株式会社 Agent d'étanchéité pour élément d'affichage électroluminescent organique, et dispositif d'affichage électroluminescent organique
CN110885619A (zh) * 2019-12-12 2020-03-17 上海华谊精细化工有限公司 一种辐照固化抗污卷材涂料及其制备方法
WO2023153387A1 (fr) * 2022-02-08 2023-08-17 三井化学株式会社 Composition polymérisable, matériau d'étanchéité, dispositif d'affichage d'image et procédé de fabrication de dispositif d'affichage d'image

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