WO2024111659A1 - Composition de résine photodurcissable, composant optique, procédé de production de composant optique, dispositif électroluminescent et procédé de production de dispositif électroluminescent - Google Patents

Composition de résine photodurcissable, composant optique, procédé de production de composant optique, dispositif électroluminescent et procédé de production de dispositif électroluminescent Download PDF

Info

Publication number
WO2024111659A1
WO2024111659A1 PCT/JP2023/042156 JP2023042156W WO2024111659A1 WO 2024111659 A1 WO2024111659 A1 WO 2024111659A1 JP 2023042156 W JP2023042156 W JP 2023042156W WO 2024111659 A1 WO2024111659 A1 WO 2024111659A1
Authority
WO
WIPO (PCT)
Prior art keywords
light
polymerizable compound
photocurable resin
resin composition
composition
Prior art date
Application number
PCT/JP2023/042156
Other languages
English (en)
Japanese (ja)
Inventor
裕基 池上
祐輔 浦岡
Original Assignee
パナソニックＩｐマネジメント株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by パナソニックＩｐマネジメント株式会社 filed Critical パナソニックＩｐマネジメント株式会社
Publication of WO2024111659A1 publication Critical patent/WO2024111659A1/fr

Links

Images

Classifications

    • 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
    • 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
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
    • 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
    • H10K50/00—Organic light-emitting devices
    • H10K50/80—Constructional details
    • H10K50/85—Arrangements for extracting light from the devices
    • H10K50/858—Arrangements for extracting light from the devices comprising refractive means, e.g. lenses
    • 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
    • H10K59/12—Active-matrix OLED [AMOLED] displays
    • H10K59/122—Pixel-defining structures or layers, e.g. banks
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
    • H10K71/10—Deposition of organic active material
    • H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
    • H10K71/13—Deposition of organic active material using liquid deposition, e.g. spin coating using printing techniques, e.g. ink-jet printing or screen printing
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10—Organic polymers or oligomers

Definitions

  • the present disclosure relates to a photocurable resin composition, an optical component, a method for manufacturing an optical component, a light-emitting device, and a method for manufacturing a light-emitting device, and more specifically to a photocurable resin composition containing a radically polymerizable compound and a photoradical polymerization initiator, an optical component made from the photocurable resin composition, a method for manufacturing an optical component using the photocurable resin composition, a light-emitting device including the optical component, and a method for manufacturing the light-emitting device.
  • the organic EL element is disposed on a support substrate, a transparent substrate is disposed opposite the support substrate, and a transparent sealant is filled between the support substrate and the transparent substrate.
  • Patent Document 1 discloses a curable composition that contains a naphthalene compound, such as 1,3-divinylnaphthalene, that has two or more vinyl groups in one molecule and has a structure in which the vinyl groups are directly bonded to the benzene ring of naphthalene, and a polymerization initiator, and contains 20 to 99 parts by mass of the naphthalene compound per 100 parts by mass of the curable composition.
  • this curable composition is useful as a sealing material for organic electroluminescence elements that can be used in applications such as display devices and lighting devices, and has a high refractive index, excellent coatability, and excellent transparency while maintaining the curing performance as a sealing material.
  • the objective of the present disclosure is to provide a photocurable resin composition that has a high refractive index when cured and that can suppress damage to the cured product when deformed, an optical component made from the photocurable resin composition, a method for manufacturing an optical component using the photocurable resin composition, a light-emitting device that includes the optical component, and a method for manufacturing the light-emitting device.
  • the photocurable resin composition contains a radical polymerizable compound (A) and a photoradical polymerization initiator (B).
  • the radical polymerizable compound (A) contains a first monofunctional radical polymerizable compound (A1) shown in formula (1), a second monofunctional radical polymerizable compound (A2) having a nitrogen atom and different from the first monofunctional radical polymerizable compound, and a multifunctional radical polymerizable compound (A3).
  • R1 is H or CH3
  • X is O or S
  • Z is a single bond or a divalent saturated hydrocarbon group.
  • An optical component according to one embodiment of the present disclosure includes a cured product of the photocurable resin composition.
  • the method for producing an optical component according to one embodiment of the present disclosure includes molding the photocurable resin composition by an inkjet method, and then irradiating the photocurable resin composition with light to cure it.
  • the light-emitting device includes a light source and an optical component that transmits light emitted by the light source, and the optical component includes a cured product of the photocurable resin composition.
  • a method for manufacturing a light-emitting device is a method for manufacturing a light-emitting device including a light source and an optical component that transmits light emitted by the light source.
  • the method includes manufacturing the optical component by the method described above.
  • FIG. 1 is a schematic cross-sectional view showing a light-emitting device according to an embodiment of the present disclosure.
  • increasing the refractive index of optical components such as the encapsulant of an organic EL element can increase the luminous efficiency of a light-emitting device equipped with the optical components.
  • deformable light-emitting devices such as foldable displays
  • the inventors considered providing optical components with a high refractive index in the deformable light-emitting device, but in that case, the optical components would be easily damaged when the light-emitting device was deformed.
  • the inventors therefore completed this disclosure in order to develop a photocurable resin composition that has a high refractive index when cured and that can suppress damage to the cured product when deformed.
  • the contents of this disclosure should not be interpreted in a limited manner based on the above-mentioned development process.
  • FIG. 1 One embodiment of the present disclosure will be described with reference to FIG. 1. Note that the following embodiment is merely a portion of the various embodiments of the present disclosure. In addition, the following embodiment can be modified in various ways depending on the design, etc., as long as the object of the present disclosure can be achieved.
  • the figures referred to below are schematic diagrams, and the dimensional ratios of the components in the figures do not necessarily reflect the actual dimensional ratios.
  • the photocurable resin composition according to this embodiment contains a radical polymerizable compound (A) and a photoradical polymerization initiator (B).
  • the radical polymerizable compound (A) contains a first monofunctional radical polymerizable compound (A1) shown in formula (1), a second monofunctional radical polymerizable compound (A2) having a nitrogen atom and different from the first monofunctional radical polymerizable compound (A1), and a polyfunctional radical polymerizable compound (A3).
  • R1 is H or CH3
  • X is O or S
  • Z is a single bond or a divalent saturated hydrocarbon group.
  • the cured product obtained by curing composition (X) has a high refractive index, and damage to the cured product during deformation can be suppressed. Therefore, when an optical component is produced from composition (X), the luminous efficiency of a light-emitting device equipped with the optical component can be increased.
  • the luminous efficiency is increased because the refractive index difference between the optical component and the inorganic film becomes smaller, particularly when the optical component is superimposed on a layer made of an inorganic material such as silicon nitride (hereinafter also referred to as an inorganic film) within the light-emitting device.
  • the first monofunctional radical polymerizable compound (A1) will be described in more detail.
  • the first monofunctional radical polymerizable compound (A1) has a biphenyl skeleton as shown in formula (1). It is speculated that the high refractive index of the cured product is achieved because the cured product has a benzene ring derived from the biphenyl skeleton of the first monofunctional radical polymerizable compound (A1) and has only one radically polymerizable functional group. It is speculated that the damage of the cured product is suppressed because the flexibility of the cured product is increased because the benzene ring constitutes the biphenyl skeleton. In addition, the first monofunctional radical polymerizable compound (A1) has a low viscosity, and therefore the first monofunctional radical polymerizable compound (A1) is less likely to deteriorate the moldability of the composition (X).
  • this divalent saturated hydrocarbon group may be linear or branched. It is more preferable that Z in formula (1) is a single bond, or that Z is a divalent hydrocarbon group and the number of carbon atoms of this divalent saturated hydrocarbon group is 1 to 5.
  • the first monofunctional radical polymerizable compound (A1) is particularly unlikely to increase the viscosity of the composition (X), and therefore the first monofunctional radical polymerizable compound (A1) is particularly unlikely to deteriorate the moldability of the composition (X).
  • the proportion of the first monofunctional radically polymerizable compound (A1) in the composition (X) is preferably 40% by mass or more and 85% by mass or less relative to the radically polymerizable compound (A). If this proportion is 40% by mass or more, the refractive index of the cured product can be further increased. If this proportion is 85% by mass or less, damage to the cured product during deformation can be further suppressed. This proportion is more preferably 45% by mass or more, and even more preferably 50% by mass or more. This proportion is more preferably 80% by mass or less, and even more preferably 75% by mass or less.
  • the monofunctional radical polymerizable compound (A2) having a second nitrogen atom will be described.
  • the second monofunctional radical polymerizable compound (A2) has only one radical polymerizable functional group in the molecule and has a nitrogen atom.
  • the monofunctional radical polymerizable compound (A2) can increase the adhesion of the cured product to the inorganic film. Therefore, when the cured product is deformed together with the inorganic film in a state where the cured product is superimposed on the inorganic film, the cured product is less likely to peel off from the inorganic film. This further suppresses damage to the cured product.
  • the monofunctional radical polymerizable compound (A2) can increase the wettability of the composition (X) with the inorganic film. Therefore, it becomes easier to apply the composition (X) onto the inorganic film and mold it.
  • the second monofunctional radical polymerizable compound (A2) may have a low viscosity. Therefore, the second monofunctional radical polymerizable compound (A2) is unlikely to deteriorate the moldability of the composition (X) or may improve the moldability of the composition (X).
  • the second monofunctional radical polymerizable compound (A2) may have high reactivity. Therefore, when the composition (X) is cured, unreacted components are unlikely to remain, and therefore outgassing from the cured product may be suppressed.
  • the second monofunctional radically polymerizable compound (A2) preferably contains at least one selected from the group consisting of a compound having an oxazoline ring, a compound having a morpholine ring, a compound having a dimethylamino group, a compound having a diethylamino group, and a compound having a pyrrolidone ring.
  • the adhesion of the cured product to the inorganic film can be further improved.
  • the compound having an oxazoline ring contains, for example, vinylmethyloxazolidinone.
  • the compound having a morpholine ring contains, for example, at least one selected from the group consisting of acryloylmorpholine and morpholin-4-yl acrylate.
  • the compound having a dimethylamino group contains, for example, at least one selected from the group consisting of dimethylacrylamide, dimethylmethacrylamide, dimethylaminopropylacrylamide, and dimethylaminopropylmethacrylamide.
  • the compound having a diethylamino group contains, for example, at least one selected from the group consisting of diethylacrylamide and diethylmethacrylamide.
  • the compound having a pyrrolidone ring contains, for example, N-vinyl-2-pyrrolidone.
  • the compounds that the second monofunctional radical polymerizable compound (A2) may contain are not limited to those mentioned above.
  • the second monofunctional radical polymerizable compound (A2) may contain a compound having a piperidine ring, such as pentamethylpiperidyl methacrylate.
  • the second monofunctional radically polymerizable compound (A2) contains vinylmethyloxazolidinone.
  • damage to the cured product can be further suppressed. This is presumably because vinylmethyloxazolidinone introduces an ester skeleton into the polymer of the radically polymerizable compound (A), thereby increasing the strength and flexibility of the cured product.
  • the proportion of the second monofunctional radically polymerizable compound (A2) in the composition (X) is preferably 5% by mass or more and 50% by mass or less relative to the radically polymerizable compound (A). If this proportion is 5% by mass or more, damage to the cured product during deformation can be further suppressed. If this proportion is 50% by mass or less, outgassing from the cured product is suppressed, and problems such as blisters and peeling are less likely to occur in optical parts containing the cured product. This proportion is more preferably 10% by mass or more, and even more preferably 15% by mass or more. Furthermore, this proportion is more preferably 45% by mass or less, and even more preferably 35% by mass or less.
  • the polyfunctional radical polymerizable compound (A3) is explained below.
  • the polyfunctional radical polymerizable compound (A3) is a compound having two or more radically polymerizable functional groups in one molecule.
  • the polyfunctional radical polymerizable compound (A3) can increase the reactivity of the composition (X). As a result, it is possible to suppress the generation of outgassing from the cured product.
  • the polyfunctional radical polymerizable compound (A3) can also increase the crosslink density of the polymer of the radical polymerizable compound (A). As a result, it is possible to increase the glass transition temperature of the cured product, thereby improving the heat resistance of the cured product.
  • polyfunctional radical polymerizable compound (A3) examples include glycerin triacrylate, 1,3-butylene glycol di(meth)acrylate, 1,4-butanediol oligoacrylate, diethylene glycol diacrylate, 1,6-hexanediol oligoacrylate, neopentyl glycol diacrylate, triethylene glycol diacrylate, tripropylene glycol diacrylate, dipropylene glycol diacrylate, cyclohexane dimethanol diacrylate, tricyclodecane dimethanol diacrylate, bisphenol A polyethoxy diacrylate, bisphenol F polyethoxy diacrylate, pentaerythritol tetraacrylate, propoxylated (2) neopentyl glycol diacrylate, trimethylolpropane triacrylate, tris(2-hydroxyethyl) diethyl) isocyanurate triacrylate, pentaerythritol triacrylate, ethoxy
  • the polyfunctional radical polymerizable compound (A3) contains glycerin triacrylate.
  • glycerin triacrylate is polyfunctional, it has a low viscosity, so that the viscosity of the composition (X) can be reduced.
  • the polyfunctional radical polymerizable compound (A3) contains glycerin triacrylate.
  • the ratio of the polyfunctional radical polymerizable compound (A3) in the composition (X) is preferably 1% by mass or more and 20% by mass or less relative to the radical polymerizable compound (A). This ratio is more preferably 2% by mass or more, and even more preferably 15% by mass or more. This ratio is more preferably 3% by mass or less, and even more preferably 10% by mass or less.
  • the photoradical polymerizable compound (A) may contain components other than those described above, as long as they do not significantly impair the effects of this embodiment.
  • the photoradical polymerizable compound (A) may contain a third monofunctional radical polymerizable compound (A4) that has only one radically polymerizable functional group in the molecule and is different from the first monofunctional radical polymerizable compound (A1) and the second monofunctional radical polymerizable compound (A2) described above.
  • the third monofunctional radical polymerizable compound (A4) is, for example, tetrahydrofurfuryl acrylate, isobornyl acrylate, 2-hydroxyethyl acrylate, 4-hydroxybutyl acrylate, isobutyl acrylate, t-butyl acrylate, isooctyl acrylate, 2-methoxyethyl acrylate, methoxytriethylene glycol acrylate, 2-ethoxyethyl acrylate, 3-methoxybutyl acrylate, ethoxyethyl acrylate, butoxyethyl acrylate, ethoxydiethylene glycol acrylate, methoxydixylethyl acrylate, ethyl diglyceryl ...
  • the third monofunctional radical polymerizable compound (A4) may contain a monofunctional radical polymerizable compound (A41) having two or more aromatic rings, different from the first monofunctional radical polymerizable compound (A1).
  • This monofunctional radical polymerizable compound (A41) can also improve the refractive index of the cured product.
  • the ratio of the monofunctional radical polymerizable compound (A41) to the radical polymerizable compound (A) is preferably 50 mass% or less, more preferably 45 mass% or less, and even more preferably 40 mass% or less.
  • the monofunctional radically polymerizable compound (A41) contains, for example, at least one of a compound represented by the following formula (2) and a compound represented by the following formula (3).
  • X1 is hydrogen or a methyl group
  • Y1 is a single bond or an alkylene group having 1 to 6 carbon atoms
  • Z1 is a single bond, S or O
  • R1 is H or a methyl group
  • L1 is a single bond, an ester bond or a thioester bond
  • n is 1 or 2, provided that when L1 is a single bond, n is 1 and m is 6 or 7.
  • X2 is a single bond or O
  • Z2 is a single bond or O
  • R2 is H or a methyl group
  • Y2 is a single bond or an alkylene group having 1 to 6 carbon atoms
  • L2 is a single bond or an ester bond.
  • the compounds represented by formula (3) exclude those in which X2 is a single bond, Z2 is a single bond, and L2 is an ester bond.
  • the photoradical polymerization initiator (B) contains at least one compound selected from the group consisting of, for example, aromatic ketones, acylphosphine oxide compounds, aromatic onium salt compounds, organic peroxides, thio compounds (thioxanthone compounds, thiophenyl group-containing compounds, etc.), hexaarylbiimidazole compounds, oxime ester compounds, borate compounds, azinium compounds, metallocene compounds, active ester compounds, compounds having a carbon-halogen bond, and alkylamine compounds.
  • the ratio of the photoradical polymerization initiator (B) to the total of the radically polymerizable compound (A) and the photoradical polymerization initiator (B) is preferably 2% by mass or more.
  • the composition (X) can have good photocurability and can also have good photocurability under an atmospheric environment. This ratio is more preferably 3% by mass or more, and even more preferably 4% by mass or more. This ratio is, for example, 15% by mass or less, preferably 12% by mass or less, and even more preferably 10% by mass or less.
  • the photoradical polymerization initiator (B) may contain a photoradical polymerization initiator having photobleaching properties.
  • the cured product of the composition (X) may have good light transmittance.
  • the ratio of the photoradical polymerization initiator having photobleaching properties to the total of the radically polymerizable compound (A) and the photoradical polymerization initiator (B) is preferably 1 mass% or more. This ratio is more preferably 2 mass% or more, and even more preferably 3 mass% or more. This ratio is, for example, 12 mass% or less, preferably 10 mass% or less, and even more preferably 8 mass% or less.
  • the photoradical polymerization initiator having photobleaching properties contains at least one of, for example, an acylphosphine oxide-based photoinitiator and a compound having photobleaching properties among oxime ester-based photoinitiators.
  • the photoradical polymerization initiator (B) may contain a component having a sensitizer skeleton in the molecule.
  • the sensitizer skeleton includes, for example, at least one of a 9H-thioxanthen-9-one skeleton and an anthracene skeleton.
  • the photoradical polymerization initiator (B) includes a component having at least one of a 9H-thioxanthen-9-one skeleton and an anthracene skeleton.
  • the photoradical polymerization initiator (B) preferably contains a compound (B1) that absorbs and becomes excited by light with a wavelength of 395 nm.
  • the reactivity of the composition (X) can be increased when the composition (X) is irradiated with ultraviolet light. It is preferable that the extinction coefficient of light with a wavelength of 395 nm of a sample obtained by dissolving the compound (B1) in acetonitrile at a concentration of 0.01 g/L is 0.1 mL/g cm or more.
  • the ratio of compound (B1) to photoradical polymerization initiator (B) is preferably 40% by mass or more.
  • the reactivity of composition (X) can be further increased when composition (X) is irradiated with ultraviolet light.
  • This ratio is more preferably 60% by mass or more, and even more preferably 80% by mass or more. There is no particular upper limit, and it may be 100% by mass. That is, this ratio is, for example, 100% by mass or less.
  • the compound (B1) contains at least one selected from the group consisting of, for example, 2-benzyl-2-(dimethylamino)-1-(4-morpholinophenyl)-1-butanone (e.g., Irgacure 369 manufactured by BASF), phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide (e.g., Irgacure 819 manufactured by BASF), 2,4,6-trimethylbenzoyl-diphenylphosphine oxide (e.g., Omnirad TPO H manufactured by IGM RESINS B.V.), and bis(2,4-cyclopentadienyl)bis[2,6-difluoro-3-(1-pyrryl)phenyl]titanium(IV) (e.g., Irgacure 784 manufactured by BASF).
  • 2-benzyl-2-(dimethylamino)-1-(4-morpholinophenyl)-1-butanone e.g
  • the composition (X) may contain a polymerization accelerator in addition to the photoradical polymerization initiator (B).
  • the polymerization accelerator contains, for example, an amine compound such as ethyl p-dimethylaminobenzoate, 2-ethylhexyl p-dimethylaminobenzoate, methyl p-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, or butoxyethyl p-dimethylaminobenzoate.
  • the components that the polymerization accelerator may contain are not limited to those mentioned above.
  • composition (X) does not contain an inorganic filler. In this case, damage to the cured product when changing the cured product of composition (X) can be further suppressed. Furthermore, in this embodiment, even if an inorganic filler is not used to increase the refractive index of the cured product, the refractive index of the cured product can be increased by the first monofunctional radically polymerizable compound (A1) shown in formula (1).
  • Composition (X) may contain an inorganic filler to the extent that the object of the present disclosure is not significantly impeded.
  • the ratio of the inorganic filler to composition (X) is preferably 25% by mass or less. It is more preferable that this ratio is 3% by mass or less.
  • the composition (X) does not contain a solvent or that the content of the solvent is 1% by mass or less. In this case, outgassing derived from the solvent is unlikely to occur from the composition (X) and the cured product of the composition (X).
  • a drying process for removing the solvent from the composition (X) and the cured product during the production of optical components and light-emitting devices can be eliminated.
  • a drying process for removing the solvent from at least one of the composition (X) and the cured product may be performed. In this case, at least one of the heating temperature and the heating time in the drying process can be reduced. Therefore, outgassing can be unlikely to occur from the optical components without reducing the production efficiency of the optical components and light-emitting devices.
  • the thickness of the composition (X) after molding is unlikely to decrease due to the evaporation of the solvent, and therefore the thickness of the optical components is unlikely to decrease. Therefore, the thickness of the optical components can be secured as large as possible while ejecting and molding the composition (X) by the inkjet method.
  • the content of the solvent is more preferably 0.5% by mass or less, even more preferably 0.3% by mass or less, and particularly preferably 0.1% by mass or less. It is particularly preferred that composition (X) does not contain a solvent or contains only a solvent that is unavoidably mixed in.
  • Composition (X) may further contain any additive other than those described above, as long as the purpose of this disclosure is not significantly impeded.
  • the composition (X) can be used to manufacture an optical component.
  • An optical component is a component that is disposed on the path of light in an optical system.
  • the composition (X) can be preferably used to manufacture an optical component that transmits light.
  • the use of the composition (X) is not limited to the manufacture of optical components, and the composition (X) can be applied to various uses that utilize its properties.
  • the refractive index of the cured product of composition (X) is preferably 1.58 or more.
  • the refractive index of the cured product is increased by this embodiment, and the cured product preferably has a refractive index of 1.58 or more.
  • the light-emitting efficiency of the light-emitting device can be particularly increased, particularly when an optical component made from composition (X) is superimposed on an inorganic film in the light-emitting device.
  • This refractive index is more preferably 1.60 or more, and even more preferably 1.62 or more.
  • the refractive index is, for example, 1.8 or less, and preferably 1.65 or less.
  • the refractive index in this disclosure is the refractive index of light with a wavelength of 589 nm in an atmosphere at 25°C.
  • the composition (X) may have a low viscosity. Therefore, the moldability of the composition (X) is good.
  • the composition (X) may be molded by discharging it by an inkjet method.
  • the composition (X) is preferably for inkjet molding. In this case, the cured product and the optical part of the composition (X) can be produced with good positional accuracy.
  • the viscosity of composition (X) at 40°C is 16 mPa ⁇ s or less.
  • the viscosity of composition (X) at 40°C is 16 mPa ⁇ s or less.
  • this viscosity is 1 mPa ⁇ s or more, and more preferably 5 mPa ⁇ s or more.
  • composition (X) at 25°C is 35 mPa ⁇ s or less. It is more preferable that the viscosity of composition (X) at 25°C is 30 mPa ⁇ s or less, even more preferable that it is 27 mPa ⁇ s or less, and particularly preferable that it is 24 mPa ⁇ s or less. It is also preferable that this viscosity is 1 mPa ⁇ s or more, more preferably 5 mPa ⁇ s or more, and also preferably 8 mPa ⁇ s or more. In these cases, composition (X) can be easily molded at room temperature, and in particular can be easily molded by the inkjet method.
  • composition (X) Such a low viscosity of composition (X) can be achieved by appropriately adjusting the composition of photoradical polymerizable compound (A) within the range described above.
  • the method and conditions for measuring the viscosity of composition (X) will be explained in detail in the Examples section below.
  • the rate of outgassing generated when the cured product of composition (X) is heated at 110°C for 30 minutes is preferably 25 ppm or less.
  • the rate of outgassing generated from the cured product is 25 ppm or less. In this case, outgassing is less likely to occur from the cured product. This makes it possible to make it difficult for voids due to outgassing to occur in a light-emitting device that includes an optical component made of the cured product, for example. This makes it difficult for water and oxygen to reach the light-emitting element through voids, making it difficult for the light-emitting element to deteriorate due to water and oxygen. It is particularly preferable for this rate of outgassing to be 15 ppm.
  • the reduction in the proportion of outgassing generated from the cured product of composition (X) can be achieved by appropriately adjusting the composition of the photoradical polymerizable compound (A) within the range described above.
  • the method for measuring the proportion of outgassing will be described in detail in the Examples below.
  • the glass transition temperature of the cured product of the composition (X) is preferably 75°C or higher.
  • the composition (X) preferably has the property of curing to become a cured product with a glass transition temperature of 75°C or higher.
  • the cured product can have good heat resistance. Therefore, for example, when the cured product is subjected to a process involving an increase in temperature, the cured product is less likely to deteriorate. Therefore, for example, when an inorganic film (e.g., passivation layer 6) that overlaps an optical component is produced by a deposition method such as a plasma CVD method, the optical component is less likely to deteriorate even if the optical component is heated.
  • an inorganic film e.g., passivation layer 6
  • the optical component can be adapted to applications such as vehicle-mounted applications that have strict requirements for heat resistance.
  • the glass transition temperature of the cured product is more preferably 80°C or higher, even more preferably 90°C or higher, and particularly preferably 100°C or higher. This glass transition temperature of the cured product can be achieved by appropriately adjusting the composition of the photoradical polymerizable compound (A) within the range described above.
  • the light-emitting device 1 includes a light source and an optical component that transmits light emitted by the light source.
  • the light-emitting device 1 includes a light-emitting element 4, and a sealant 5 and a passivation layer 6 that cover the light-emitting element 4.
  • the light-emitting element 4 is the light source
  • the sealant 5 is the optical component
  • the passivation layer 6 is an inorganic film.
  • the sealant 5 and the passivation layer 6 overlap each other.
  • the light-emitting element 4 includes, for example, a light-emitting diode.
  • the light-emitting diode includes, for example, at least one of an organic EL element (organic light-emitting diode) and a micro light-emitting diode.
  • the light-emitting device 1 including the light-emitting element 4 is, for example, an organic EL display.
  • the light-emitting element 4 includes a micro light-emitting diode
  • the light-emitting device 1 including the light-emitting element 4 is, for example, a micro LED display.
  • EL is an abbreviation for electroluminescence.
  • the light-emitting device 1 is a top-emission type.
  • the light-emitting device 1 includes a support substrate 2, a transparent substrate 3 that faces the support substrate 2 with a gap therebetween, a light-emitting element 4 on the surface of the support substrate 2 that faces the transparent substrate 3, and a passivation layer 6 and a sealing material 5 that cover the light-emitting element 4.
  • the support substrate 2 is made of, for example, but not limited to, a resin material.
  • the transparent substrate 3 is made of a light-transmitting material.
  • the transparent substrate 3 is, for example, a glass substrate or a transparent resin substrate.
  • the light-emitting element 4 includes, for example, a pair of electrodes 41, 43 and an organic light-emitting layer 42 between the electrodes 41, 43.
  • the organic light-emitting layer 42 includes, for example, a hole injection layer 421, a hole transport layer 422, an organic light-emitting layer 423, and an electron transport layer 424, and these layers are stacked in the above order.
  • the light-emitting device 1 includes a plurality of light-emitting elements 4, which form an array 9 (hereinafter referred to as element array 9) on a support substrate 2.
  • the element array 9 also includes a partition 7.
  • the partition 7 is on the support substrate 2 and separates two adjacent light-emitting elements 4.
  • the partition 7 is fabricated, for example, by forming a photosensitive resin material using a photolithography method.
  • the element array 9 also includes connection wiring 8 that electrically connects the electrodes 43 and electron transport layers 424 of adjacent light-emitting elements 4.
  • the connection wiring 8 is provided on the partition 7.
  • the passivation layer 6 corresponds to an inorganic film.
  • the passivation layer 6 is preferably made of silicon nitride or silicon oxide, and is particularly preferably made of silicon nitride.
  • the passivation layer 6 includes a first passivation layer 61 and a second passivation layer 62.
  • the first passivation layer 61 covers the element array 9 while being in direct contact with the element array 9, thereby covering the light-emitting element 4.
  • the second passivation layer 62 is disposed on the opposite side of the element array 9 with respect to the first passivation layer 61, and a gap is provided between the second passivation layer 62 and the first passivation layer 61.
  • the sealant 5 is filled between the first passivation layer 61 and the second passivation layer 62. That is, the first passivation layer 61 is interposed between the light-emitting element 4 and the sealant 5 covering the light-emitting element 4.
  • a second sealing material 52 is filled between the second passivation layer 62 and the transparent substrate 3.
  • the second sealing material 52 is made of, for example, a transparent resin material. There are no particular limitations on the material of the second sealing material 52.
  • the material of the second sealing material 52 may be the same as or different from the sealing material 5.
  • the composition (X) it is preferable to eject the composition (X) by an inkjet method to form a film, and then irradiate the composition (X) with ultraviolet light to harden it, thereby producing the sealing material 5.
  • the composition (X) can be ejected and shaped by an inkjet method.
  • the composition (X) When discharging the composition (X) by the inkjet method, if the composition (X) has a sufficiently low viscosity at room temperature, for example, if the viscosity at 25°C is 30 mPa ⁇ s or less, particularly 16 mPa ⁇ s or less, the composition (X) can be molded by discharging it by the inkjet method without heating it. If the viscosity of the composition (X) is reduced by heating, the composition (X) may be heated and then discharged by the inkjet method to be molded.
  • the viscosity of the composition (X) at 40°C is particularly 16 mPa ⁇ s or less
  • the viscosity of the composition (X) can be reduced by simply heating it slightly, and this reduced-viscosity composition (X) can be discharged by the inkjet method.
  • the heating temperature of the composition (X) is, for example, 20°C or higher and 50°C or lower.
  • the support substrate 2 is prepared. On one surface of the support substrate 2, partition walls 7 are fabricated by photolithography using, for example, a photosensitive resin material. Next, a plurality of light-emitting elements 4 are provided on one surface of the support substrate 2.
  • the light-emitting elements 4 can be fabricated by an appropriate method such as a vapor deposition method or a coating method. In particular, it is preferable to fabricate the light-emitting elements 4 by a coating method such as an inkjet method. In this way, an element array 9 is fabricated on the support substrate 2.
  • the first passivation layer 61 is provided on the element array 9.
  • the first passivation layer 61 can be produced by a deposition method such as a plasma CVD method.
  • the composition (X) is ejected onto the first passivation layer 61, for example, by an inkjet method, and shaped to produce a coating film.
  • the inkjet method to both the formation of the light-emitting element 4 and the shaping of the composition (X)
  • the manufacturing efficiency of the light-emitting device 1 can be particularly improved.
  • the coating film of the composition (X) is cured by irradiating it with light, producing the encapsulant 5.
  • composition (X) When irradiating composition (X) with light, composition (X) may be irradiated with light in an atmosphere containing oxygen, such as an air atmosphere, or composition (X) may be irradiated with light in an inert atmosphere, such as a nitrogen atmosphere.
  • atmosphere containing oxygen such as an air atmosphere
  • composition (X) may be irradiated with light in an inert atmosphere, such as a nitrogen atmosphere.
  • the second passivation layer 62 is provided on the sealing material 5.
  • the second passivation layer 62 can be produced by a deposition method such as plasma CVD.
  • a photocurable resin material is applied to one surface of the support substrate 2 so as to cover the second passivation layer 62, and then the transparent substrate 3 is placed on top of this resin material.
  • the transparent substrate 3 is, for example, a glass substrate or a transparent resin substrate.
  • ultraviolet light is applied from the outside toward the transparent substrate 3.
  • the ultraviolet light passes through the transparent substrate 3 and reaches the photocurable resin material. This causes the photocurable resin material to harden, producing the second sealing material 52.
  • the cured product of composition (X) can have a high refractive index, so even if the sealant 5 overlaps the passivation layer 6, which is an inorganic film, a decrease in luminous efficiency is unlikely to occur.
  • the thickness of the sealing material 5 is, for example, 1 ⁇ m or more and 50 ⁇ m or less.
  • the thickness of the sealing material 5 is more preferably 20 ⁇ m or less, and even more preferably 15 ⁇ m or less.
  • the light emitting device 1 can be thinned, and it is also possible to obtain a flexible light emitting device 1, i.e., a bendable light emitting device.
  • the thickness of the sealing material 5 is preferably 3 ⁇ m or more, more preferably 5 ⁇ m or more, and even more preferably 8 ⁇ m or more.
  • the thickness of the passivation layer 6 overlapping the sealing material 5 is, for example, 0.1 ⁇ m or more and 2 ⁇ m or less.
  • the passivation layer 6 includes the first passivation layer 61 and the second passivation layer 62 as described above, it is preferable that the thickness of each of the first passivation layer 61 and the second passivation layer 62 is 0.1 ⁇ m or more and 2 ⁇ m or less.
  • composition (X) is not limited to the preparation of the encapsulant 5 for the light-emitting element 4.
  • the composition (X) can be used to prepare various optical components that transmit light emitted by a light source.
  • the optical component may be a color resist. That is, for example, a phosphor may be contained in the composition (X), and a color resist in a color filter may be prepared from this composition (X).
  • This color filter can be provided in a display device such as an organic EL display or a micro LED display, which is a light-emitting device.
  • the photocurable resin composition according to the first aspect contains a radical polymerizable compound (A) and a photoradical polymerization initiator (B).
  • the radical polymerizable compound (A) contains a first monofunctional radical polymerizable compound (A1) represented by formula (1), a monofunctional radical polymerizable compound (A2) having a nitrogen atom different from the first monofunctional radical polymerizable compound (A1), and a polyfunctional radical polymerizable compound (A3).
  • R1 is H or CH3
  • X is O or S
  • Z is a single bond or a divalent saturated hydrocarbon group.
  • the cured product of the photocurable resin composition has a high refractive index, and damage to the cured product during deformation can be suppressed.
  • the monofunctional radically polymerizable compound (A2) having a nitrogen atom in the first embodiment contains at least one compound selected from the group consisting of a compound having an oxazoline ring, a compound having a morpholine ring, a compound having a dimethylamino group, a compound having a diethylamino group, and a compound having a pyrrolidone ring.
  • damage to the cured material during deformation can be further suppressed, especially when the cured material is layered on top of the inorganic film.
  • the photoradical polymerization initiator (B) contains a compound (B1) that absorbs and becomes excited by light having a wavelength of 395 nm.
  • the photocurable resin composition can have particularly high UV curability, which can suppress outgassing from the cured product.
  • the ratio of the first monofunctional radically polymerizable compound (A1) shown in formula (1) to the radically polymerizable compound (A) is 40% by mass or more and 85% by mass or less.
  • the proportion of the second monofunctional radically polymerizable compound (A2) is 5% by mass or more and 50% by mass or less relative to the radically polymerizable compound (A).
  • the viscosity of the photocurable resin composition at 40°C is 16 mPa ⁇ s or less.
  • the photocurable resin composition has good moldability, and it is easy to eject and mold the photocurable resin composition using an inkjet method.
  • the refractive index of the cured product of the photocurable resin composition is 1.58 or more and 1.65 or less.
  • the photocurable resin composition can have a refractive index close to that of the inorganic film.
  • the photocurable resin composition does not contain an inorganic filler.
  • the optical component according to the ninth aspect includes a cured product of the photocurable resin composition according to any one of the first to eighth aspects.
  • the optical component has a high refractive index, and damage to the optical component during deformation can be suppressed.
  • the method for producing an optical component according to the tenth aspect includes molding the photocurable resin composition according to any one of the first to eighth aspects by an inkjet method, and then irradiating the photocurable resin composition with light to cure it.
  • This method allows optical components to be manufactured with high positional accuracy and reduces the risk of yield degradation.
  • the light-emitting device (1) according to the eleventh aspect includes a light source and an optical component that transmits light emitted by the light source, and the optical component includes a cured product of the photocurable resin composition according to any one of the first to eighth aspects.
  • the optical components of the light-emitting device (1) have a high refractive index, and damage to the optical components during deformation can be suppressed.
  • the method for manufacturing a light-emitting device (1) according to the twelfth aspect is a method for manufacturing a light-emitting device (1) that includes a light source and an optical component that transmits light emitted by the light source, and includes manufacturing the optical component by the method according to the tenth aspect.
  • the optical components in the light emitting device (1) can be manufactured with high positional accuracy, and the yield is less likely to deteriorate.
  • compositions of the examples and comparative examples were prepared by mixing the components shown in the table below. Details of the components shown in the table are as follows.
  • the "proportion of the first monofunctional compound” in the table is the total proportion of the first monofunctional compounds #1 to #3, which are the first monofunctional radical polymerizable compounds, to the total amount of the radical polymerizable compounds.
  • the "proportion of the second monofunctional compound” in the table is the total proportion of the second monofunctional compounds #1 to #5, which are the second monofunctional radical polymerizable compounds, to the total amount of the radical polymerizable compounds.
  • First monofunctional compound #1 A compound represented by the following chemical formula (11), manufactured by Kyoeisha Chemical Co., Ltd.
  • Product name Light Acrylate OPP
  • Second monofunctional compound #1 Vinylmethyloxazolidinone, manufactured by BASF.
  • Second monofunctional compound #2 acryloylmorpholine, manufactured by KJ Chemicals Co., Ltd.
  • Second monofunctional compound #3 Dimethylacrylamide, manufactured by KJ Chemicals Co., Ltd.
  • Second monofunctional compound #4 Diethylacrylamide, manufactured by KJ Chemicals Co., Ltd.
  • Second monofunctional compound #5 N-vinyl-2-pyrrolidone, manufactured by BASF.
  • -Third monofunctional compound #1 A compound represented by the following chemical formula (31), manufactured by Kyoeisha Chemical Co., Ltd. Product name: OPPEA.
  • glycerin triacrylate Manufactured by Toagosei Co., Ltd. Product name: M-930.
  • Initiator #1 2,4,6-trimethylbenzoyl-diphenylphosphine oxide, manufactured by IGM RESINS B.V.
  • Initiator #2 Oxime ester-based photoradical polymerization initiator, manufactured by BASF Japan Ltd.
  • Viscosity at 25° C The viscosity of the composition was measured using a rheometer (Model DHR-2, manufactured by Anton Paar Japan) at a temperature of 25° C. and a shear rate of 1000 s ⁇ 1 .
  • Viscosity at 40° C The viscosity of the composition was measured using a rheometer (Model DHR-2, manufactured by Anton Paar Japan) at a temperature of 40° C. and a shear rate of 1000 s ⁇ 1 .
  • composition was measured with an infrared spectrometer (Agilent Cary 610 FTIR Microscope System, manufactured by Agilent Technologies) to obtain an IR spectrum.
  • infrared spectrometer Alignment Cary 610 FTIR Microscope System, manufactured by Agilent Technologies
  • the composition was applied to prepare a coating film having a thickness of 10 ⁇ m, and the coating film was irradiated with light having a peak wavelength of 395 nm under a nitrogen atmosphere using a UV irradiator (manufactured by Ushio Inc., model number Unijet E075IIHD) under conditions of an irradiation intensity of 0.5 W/cm 2 and an integrated light quantity of 1.5 J/cm 2.
  • the composition (cured product) after irradiation with ultraviolet light was then measured with the above-mentioned infrared spectrometer to obtain an IR spectrum.
  • the peak intensity of the absorption of the acryloyl group appearing at 810 cm -1 was measured in each of the two IR spectra.
  • the reduction rate of the reactive functional group in the composition before and after irradiation with ultraviolet light was calculated using the formula ⁇ 1- ( I0 - I1 )/ I0 ⁇ x 100(%) from the peak intensity I0 for the coating film and the peak intensity I1 for the cured product. The result was taken as the reaction rate, and the reaction rate was evaluated as "A" for 90% or more, "B” for 80% or more but less than 90%, and "C" for less than 80%.
  • the composition was heated at 110°C for 30 minutes, and then the gas phase portion in the vial was introduced into a gas chromatograph for analysis.
  • the concentration of the outgassing generated from the composition was specified based on the peak area of the obtained gas chromatogram.
  • the concentration of the outgassing is the volume fraction of the outgassing in the gas phase of the vial relative to the volume of the vial (22 mL).
  • the outgassing concentration was determined using toluene as the standard substance. Specifically, two standard samples with toluene concentrations of 1000 ppm and 100 ppm were prepared by volatilizing toluene in a vial. Each standard sample was introduced into a gas chromatograph for analysis. From the peak areas of the two chromatograms obtained in this way, the relationship between peak area and concentration was determined, and the above-mentioned outgassing concentration was determined based on these results.
  • a coating film was formed by applying a composition to a thickness of 10 ⁇ m on this inorganic film, and this coating film was irradiated with light having a peak wavelength of 395 nm under a nitrogen atmosphere using a UV irradiator (manufactured by Ushio Electric, model number Unijet E075IIHD) under conditions of an irradiation intensity of 0.5 W/cm 2 and an integrated light quantity of 1.5 J/cm 2.
  • a UV irradiator manufactured by Ushio Electric, model number Unijet E075IIHD
  • This coating film was pulled in a 90 degree direction with an autograph (manufactured by Shimadzu Corporation, model number AGS-X) to measure the peel strength.
  • the peel strength was evaluated as "A” when it was 100 mN/cm or more, "B” when it was 50 mN/cm or more, “C” when it was 20 mN/cm or more, and "D” when it was less than 20 mN/cm.
  • a coating film was formed by applying the composition to a thickness of 10 ⁇ m on the inorganic film, and the coating film was irradiated with light having a peak wavelength of 395 nm under a nitrogen atmosphere using a UV irradiator (manufactured by Ushio Electric, model number Unijet E075IIHD) under conditions of an irradiation intensity of 0.5 W/cm 2 and an integrated light amount of 1.5 J/cm 2 to produce a film having a thickness of 10 ⁇ m.
  • a UV irradiator manufactured by Ushio Electric, model number Unijet E075IIHD
  • This evaluation sample was subjected to a test in which it was repeatedly bent 100,000 times under conditions in which the radius of curvature of the bent portion was 1.5 mm, 2.0 mm, and 5.0 mm.
  • the film for evaluation was rated as "A” if there was no peeling or cracking in the film after testing under any of the conditions, as “B” if there was no peeling or cracking in the film after testing under the bending radius conditions of 2.0 mm and 5.0 mm, and peeling and cracking in the film after testing under the bending radius condition of 1.5 mm, as “C” if there was no peeling or cracking in the film after testing under the bending radius condition of 5.0 mm, but peeling and cracking in the film after testing under the bending radius conditions of 1.5 mm and 2.0 mm, and as “D” if there was cracking and peeling in the film after testing under any of the conditions.
  • Glass transition temperature A coating film was prepared by applying the composition, and the coating film was photocured by irradiating the coating film under atmospheric conditions with light having a peak wavelength of 395 nm using a UV irradiator (manufactured by Ushio Inc., model number E075IIHD) under conditions of an irradiation intensity of 3 W/ cm2 and an integrated light quantity of 15 J/ cm2, thereby preparing a film having a thickness of 500 ⁇ m.
  • the glass transition temperature of a sample cut out from the film was measured using a viscoelasticity measuring device (manufactured by Hitachi High-Tech Science Corporation, model number DMA7100).

Landscapes

  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Optics & Photonics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Manufacturing & Machinery (AREA)
  • General Physics & Mathematics (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente divulgation concerne une composition de résine photodurcissable qui produit des produits durcis qui ont un indice de réfraction élevé et peuvent supprimer la rupture des produits durcis pendant la déformation. Une composition de résine photodurcissable selon la présente invention contient un composé polymérisable par voie radicalaire (A) et un initiateur de polymérisation photo-radicalaire (B). Le composé polymérisable par voie radicalaire (A) contient un premier composé polymérisable par voie radicalaire monofonctionnel (A1) qui est représenté par la formule (1), un second composé polymérisable par voie radicalaire monofonctionnel (A2) qui est différent du premier composé polymérisable par voie radicalaire et comprend un atome d'azote, et un composé polymérisable par voie radicalaire polyfonctionnel (A3). Dans la formule (1), R1 est H ou CH3, X est O ou S, et Z est une liaison simple ou un groupe hydrocarboné saturé bivalent.
PCT/JP2023/042156 2022-11-25 2023-11-24 Composition de résine photodurcissable, composant optique, procédé de production de composant optique, dispositif électroluminescent et procédé de production de dispositif électroluminescent WO2024111659A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2022-188670 2022-11-25
JP2022188670 2022-11-25

Publications (1)

Publication Number Publication Date
WO2024111659A1 true WO2024111659A1 (fr) 2024-05-30

Family

ID=91196113

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2023/042156 WO2024111659A1 (fr) 2022-11-25 2023-11-24 Composition de résine photodurcissable, composant optique, procédé de production de composant optique, dispositif électroluminescent et procédé de production de dispositif électroluminescent

Country Status (1)

Country Link
WO (1) WO2024111659A1 (fr)

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5130750A (fr) * 1974-07-04 1976-03-16 Smith & Nephew Res
JP2005272773A (ja) * 2004-03-26 2005-10-06 Toagosei Co Ltd 活性エネルギー線硬化型光学材料用組成物
WO2018062196A1 (fr) * 2016-09-28 2018-04-05 旭硝子株式会社 Composition durcissable et produit durci
JP2018104696A (ja) * 2016-12-26 2018-07-05 旭硝子株式会社 重合性化合物、硬化性組成物および硬化物
CN111154028A (zh) * 2020-01-06 2020-05-15 东南大学 一种高折射率角膜接触镜材料及其应用
US20200249568A1 (en) * 2019-02-05 2020-08-06 Facebook Technologies, Llc Curable formulation with high refractive index and its application in surface relief grating using nanoimprinting lithography
JP2022123808A (ja) * 2021-02-12 2022-08-24 大阪有機化学工業株式会社 硬化性樹脂組成物

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5130750A (fr) * 1974-07-04 1976-03-16 Smith & Nephew Res
JP2005272773A (ja) * 2004-03-26 2005-10-06 Toagosei Co Ltd 活性エネルギー線硬化型光学材料用組成物
WO2018062196A1 (fr) * 2016-09-28 2018-04-05 旭硝子株式会社 Composition durcissable et produit durci
JP2018104696A (ja) * 2016-12-26 2018-07-05 旭硝子株式会社 重合性化合物、硬化性組成物および硬化物
US20200249568A1 (en) * 2019-02-05 2020-08-06 Facebook Technologies, Llc Curable formulation with high refractive index and its application in surface relief grating using nanoimprinting lithography
CN111154028A (zh) * 2020-01-06 2020-05-15 东南大学 一种高折射率角膜接触镜材料及其应用
JP2022123808A (ja) * 2021-02-12 2022-08-24 大阪有機化学工業株式会社 硬化性樹脂組成物

Similar Documents

Publication Publication Date Title
WO2022203081A1 (fr) Composition de résine photodurcissable, composant optique, procédé de production de composant optique et dispositif électroluminescent
JP7236671B2 (ja) 発光素子封止用組成物、及び発光装置
JP7320793B2 (ja) 紫外線硬化性樹脂組成物、有機ｅｌ発光装置、及びタッチパネル
JP2023156307A (ja) 紫外線硬化性樹脂組成物、発光装置の製造方法、発光装置、及びタッチパネル
JP7170246B2 (ja) 紫外線硬化性樹脂組成物、発光装置の製造方法及び発光装置
WO2024111659A1 (fr) Composition de résine photodurcissable, composant optique, procédé de production de composant optique, dispositif électroluminescent et procédé de production de dispositif électroluminescent
WO2024117094A1 (fr) Composition de résine photodurcissable, composant optique, procédé de production de composant optique, dispositif émetteur de lumière, et procédé de production de dispositif émetteur de lumière
JP7228804B2 (ja) 紫外線硬化性樹脂組成物、カラーフィルタ、発光装置、カラーフィルタの製造方法及び発光装置の製造方法
JP2023081885A (ja) 封止材の製造方法、及び発光装置の製造方法
JP7489607B2 (ja) 紫外線硬化性樹脂組成物、有機ｅｌ発光装置の製造方法及び有機ｅｌ発光装置
JP7442121B2 (ja) 紫外線硬化性樹脂組成物、カラーレジスト、カラーフィルタ、発光装置及びカラーレジストの製造方法
WO2022080359A1 (fr) Composition de moulage d'élément de conversion de longueur d'onde, réserve colorée, filtre coloré, procédé de fabrication de réserve colorée, dispositif électroluminescent et procédé de fabrication de dispositif électroluminescent
JP2024083352A (ja) 紫外線硬化性樹脂組成物、発光装置の製造方法及び発光装置
CN113248952B (zh) 紫外线固化性树脂组合物、光学部件及其制造方法、发光装置及其制造方法
JP2021123693A (ja) 紫外線硬化性樹脂組成物、光学部品、光学部品の製造方法、発光装置、及び発光装置の製造方法
CN112578634A (zh) 紫外线固化性树脂组合物、彩色滤光片、彩色抗蚀剂和发光装置及它们的制造方法
CN114316650A (zh) 紫外线固化性树脂组合物、光学部件、光学部件的制造方法、发光装置及其制造方法
CN114686122A (zh) 有机el元件用密封剂、密封膜、有机el元件及有机el元件的制造方法
JP2020056024A (ja) 紫外線硬化性樹脂組成物、発光装置の製造方法及び発光装置
JP2022142674A (ja) 光硬化性樹脂組成物、光学部品、光学部品の製造方法、発光装置、及び発光装置の製造方法
JP2022142673A (ja) 光硬化性樹脂組成物、光学部品、光学部品の製造方法、発光装置、及び発光装置の製造方法
JP2022142676A (ja) 光硬化性樹脂組成物、光学部品、光学部品の製造方法、発光装置、及び発光装置の製造方法
JP2022093086A (ja) 紫外線硬化性樹脂組成物、光学部品、光学部品の製造方法、発光装置、及び発光装置の製造方法
JP2022068006A (ja) 波長変換部材成形用組成物、カラーレジスト、カラーフィルタ、カラーレジストの製造方法、発光装置、及び発光装置の製造方法
TW202219203A (zh) 噴墨塗布用及led保護用硬化性組合物、led模組、led模組之製造方法及led顯示裝置