Photocurable resin composition, optical member, method for producing optical member, light-emitting device, and method for producing light-emitting device

Abstract

Provided is a photocurable resin composition which has a high refractive index of a cured product and is capable of suppressing breakage of the cured product during deformation. The photocurable resin composition contains a radical polymerizable compound (A) and a photoradical polymerization initiator (B). The radically polymerizable compound (A) contains a first monofunctional radically polymerizable compound (A1) represented by formula (1), a second monofunctional radically polymerizable compound (A2) different from the first radically polymerizable compound and having a nitrogen atom, and a polyfunctional radically polymerizable compound (A3). In formula (1), R1 is H or CH3, X is O or S, and Z is a single bond or a divalent saturated hydrocarbon group. # imgabs0 #

Description

Technical Field

[0001] 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. More specifically, the present disclosure relates to a photocurable resin composition containing a radically polymerizable compound and a photo radical polymerization initiator, an optical component made from the above photocurable resin composition, a method for manufacturing an optical component using the above photocurable resin composition, a light-emitting device including the above optical component, and a method for manufacturing the above light-emitting device. Background Art

[0002] In a light-emitting device having a light-emitting element such as an organic EL element as a light source, for example, an organic EL element is disposed on a support substrate, a transparent substrate is disposed so as to face the support substrate, and a transparent sealing material is filled between the support substrate and the transparent substrate.

[0003] For example, Patent Document 1 discloses a curable composition containing a naphthalene compound having a structure in which two or more vinyl groups are present in one molecule and the vinyl group is directly bonded to the benzene ring of naphthalene, such as 1,3-divinylnaphthalene, and a polymerization initiator. The naphthalene compound is contained in the range of 20 parts by mass to 99 parts by mass with respect to 100 parts by mass of the curable composition. According to the disclosure of Patent Document 1, this curable composition is useful as a sealing material for an organic electroluminescent element that can be applied to uses such as a display device and a lighting device, has a high refractive index while maintaining the curing performance as a sealing material, and is excellent in coatability and transparency.

[0004] Prior Art Documents

[0005] Patent Documents

[0006] Patent Document 1: Japanese Unexamined Patent Application Publication No. 2020-26515 Summary of the Invention

[0007] An object of the present disclosure is to provide a photocurable resin composition in which a cured product has a high refractive index and can suppress breakage of the cured product during deformation, an optical component made from the above photocurable resin composition, a method for manufacturing an optical component using the above photocurable resin composition, a light-emitting device including the above optical component, and a method for manufacturing the above light-emitting device.

[0008] A photocurable resin composition according to one aspect of the present disclosure contains a radically polymerizable compound (A) and a photo radical polymerization initiator (B). The radically polymerizable compound (A) contains: a first monofunctional radically polymerizable compound (A1) represented by formula (1), a second monofunctional radically polymerizable compound (A2) different from the first monofunctional radically polymerizable compound and having a nitrogen atom, and a polyfunctional radically polymerizable compound (A3).

[0009] [Chemical Formula 1]

[0010]

[0011] In formula (1), R1 is H or CH 3 , X is O or S, and Z is a single bond or a divalent saturated hydrocarbon group.

[0012] An optical component according to one embodiment of the present disclosure includes a cured product of the above-described photocurable resin composition.

[0013] A method for manufacturing an optical component according to one embodiment of the present disclosure includes a step of forming the above-described photocurable resin composition by an inkjet method and then curing the photocurable resin composition by irradiating it with light.

[0014] A light-emitting device according to one embodiment of the present disclosure includes a light source and an optical component that transmits light emitted from the light source, and the optical component includes a cured product of the above-described photocurable resin composition.

[0015] A method for manufacturing a light-emitting device according to one embodiment of the present disclosure is a method for manufacturing a light-emitting device including a light source and an optical component that transmits light emitted from the light source. This method includes a step of manufacturing the above-described optical component by the above-described method. BRIEF DESCRIPTION OF THE DRAWINGS

[0016] Figure 1 is a schematic cross-sectional view showing a light-emitting device according to one embodiment of the present disclosure. DETAILED DESCRIPTION

[0017] According to the investigation by the inventors, if the refractive index of an optical component such as a sealing material of an organic EL element is increased, the luminous efficiency of a light-emitting device including the optical component can be improved.

[0018] However, when using the curable composition disclosed in Patent Document 1 (Japanese Unexamined Patent Application Publication No. 2020-26515) to produce a sealing material, although the refractive index of the sealing material is increased, the flexibility of the cured product of the curable composition becomes low.

[0019] In recent years, deformable light-emitting devices typified by foldable displays have been continuously provided. The inventors have studied the provision of an optical component having a high refractive index in a deformable light-emitting device. However, in this case, if the light-emitting device is deformed, the optical component is likely to be damaged.

[0020] Therefore, the inventors completed the present application in order to develop a photocurable resin composition in which the cured product has a high refractive index and the breakage of the cured product during deformation can be suppressed. However, the content of the present disclosure is not construed in a limiting manner by the above-described development process.

[0021] Reference Figure 1 An embodiment of the present disclosure will be described. It should be noted that the following embodiments are only a part of various embodiments of the present disclosure. In addition, as long as the following embodiments can achieve the purpose of the present disclosure, various changes can be made according to design and the like. The drawings referred to below are schematic drawings, and the dimensional ratios of the components in the drawings do not necessarily reflect the actual dimensional ratios.

[0022] The photocurable resin composition of the present embodiment (hereinafter, also referred to as composition (X)) contains a radically polymerizable compound (A) and a photo radical polymerization initiator (B). The radically polymerizable compound (A) contains a first monofunctional radically polymerizable compound (A1) represented by formula (1), a second monofunctional radically polymerizable compound (A2) different from the first monofunctional radically polymerizable compound (A1) and having a nitrogen atom, and a polyfunctional radically polymerizable compound (A3).

[0023] [Chemical formula 2]

[0024]

[0025] In formula (1), R1 is H or CH 3 , X is O or S, and Z is a single bond or a divalent saturated hydrocarbon group.

[0026] According to the present embodiment, the cured product obtained by curing the composition (X) has a high refractive index and can suppress the breakage of the cured product during deformation. Therefore, if an optical component is made of the composition (X), the luminous efficiency of a light-emitting device including the optical component can be improved. The improvement in luminous efficiency is because, particularly when the optical component is overlapped with a layer made of an inorganic material such as silicon nitride (hereinafter, also referred to as an inorganic film) in a light-emitting device, the refractive index difference between the optical component and the inorganic film becomes smaller.

[0027] The first monofunctional radically polymerizable compound (A1) will be described in more detail. The first monofunctional radically polymerizable compound (A1) has a biphenyl skeleton as shown in formula (1). It is presumed that the high refractive index of the cured product is achieved particularly because the cured product has a benzene ring derived from the biphenyl skeleton of the first monofunctional radically polymerizable compound (A1) and has only one radically polymerizable functional group. In addition, it is presumed that the breakage of the cured product is suppressed because the benzene ring forms a biphenyl skeleton, so the flexibility of the cured product is improved. In addition, the viscosity of the first monofunctional radically polymerizable compound (A1) is low, so the first monofunctional radically polymerizable compound (A1) is less likely to deteriorate the formability of the composition (X).

[0028] When Z in formula (1) is a divalent saturated hydrocarbon group, the divalent saturated hydrocarbon group may be linear or may have a branched chain. More preferably, Z in formula (1) is a single bond, or Z is a divalent hydrocarbon group and the number of carbon atoms of the divalent saturated hydrocarbon group is 1 or more and 5 or less. In this case, the first monofunctional radically polymerizable compound (A1) is particularly unlikely to increase the viscosity of the composition (X), and thus the first monofunctional radically polymerizable compound (A1) is particularly unlikely to deteriorate the moldability of the composition (X).

[0029] 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, breakage of the cured product during deformation can be further suppressed. This proportion is more preferably 45% by mass or more, and further preferably 50% by mass or more. This proportion is more preferably 80% by mass or less, and further preferably 75% by mass or less.

[0030] The second monofunctional radically polymerizable compound (A2) having a nitrogen atom will be described. The second monofunctional radically polymerizable compound (A2) has only one radically polymerizable functional group in the molecule and has a nitrogen atom. The monofunctional radically polymerizable compound (A2) can improve the adhesion of the cured product to the inorganic film. Therefore, when the cured product deforms together with the inorganic film in a state where the cured product and the inorganic film overlap, the cured product is not easily peeled off from the inorganic film. As a result, breakage of the cured product is further suppressed. The monofunctional radically polymerizable compound (A2) can improve the wettability of the composition (X) with the inorganic film. Therefore, it is easy to coat the composition (X) on the inorganic film for molding.

[0031] In addition, the second monofunctional radically polymerizable compound (A2) may have a low viscosity. Therefore, the second monofunctional radically polymerizable compound (A2) is less likely to deteriorate the moldability of the composition (X), or can improve the moldability of the composition (X). In addition, the second monofunctional radically polymerizable compound (A2) can have high reactivity. Therefore, when the composition (X) is cured, unreacted components are less likely to remain, and thus generation of outgassing from the cured product can be suppressed.

[0032] The second monofunctional radically polymerizable compound (A2) preferably contains at least one selected from 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. In this case, the adhesion between the cured product and the inorganic film can be further improved.

[0033] Compounds having an oxazoline ring include, for example, vinylmethyl oxazolidinone. Compounds having a morpholine ring include, for example, at least one selected from acryloylmorpholine and morpholin-4-yl acrylate. Compounds having a dimethylamino group include, for example, at least one selected from dimethylacrylamide, dimethylmethacrylamide, dimethylaminopropylacrylamide, and dimethylaminopropylmethacrylamide. Compounds having a diethylamino group include, for example, at least one selected from diethylacrylamide and diethylmethacrylamide. Compounds having a pyrrolidone ring include, for example, N-vinyl-2-pyrrolidone.

[0034] It should be noted that the compounds that the second monofunctional radically polymerizable compound (A2) can contain are not limited to the above. For example, the second monofunctional radically polymerizable compound (A2) can contain compounds having a piperidine ring such as pentamethylpiperidyl methacrylate.

[0035] Particularly preferably, the second monofunctional radically polymerizable compound (A2) contains vinylmethyl oxazolidinone. In this case, breakage of the cured product can be further suppressed. It is presumed that this is because by introducing an ester skeleton into the polymer of the radically polymerizable compound (A) using vinylmethyl oxazolidinone, the strength and flexibility of the cured product can be improved.

[0036] Relative to the radically polymerizable compound (A), 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. If this proportion is 5% by mass or more, breakage during deformation of the cured product can be further suppressed. If this proportion is 50% by mass or less, the generation of evolved gas from the cured product is suppressed, and problems such as foaming and peeling are less likely to occur in optical components and the like containing the cured product. This proportion is more preferably 10% by mass or more, and further preferably 15% by mass or more. In addition, this proportion is more preferably 45% by mass or less, and further preferably 35% by mass or less.

[0037] The polyfunctional radically polymerizable compound (A3) will be described. The polyfunctional radically polymerizable compound (A3) is a compound having two or more radically polymerizable functional groups in one molecule. The polyfunctional radically polymerizable compound (A3) can improve the reactivity of the composition (X). Therefore, the generation of evolved gas from the cured product can be suppressed. The polyfunctional radically polymerizable compound (A3) can also increase the crosslinking density of the polymer of the radically polymerizable compound (A). Therefore, the glass transition temperature of the cured product can be increased, thereby improving the heat resistance of the cured product.

[0038] The polyfunctional free-radical polymerizable compound (A3) contains, for example, at least one selected from the group consisting of glycerol triacrylate, 1,3-butanediol 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, cyclohexanedimethanol diacrylate, tricyclodecanedimethanol diacrylate, bisphenol A polyethoxy diacrylate, bisphenol F polyethoxy diacrylate, pentaerythritol tetraacrylate, propoxylated (2) neopentyl glycol diacrylate, trimethylolpropane triacrylate, tris(2-hydroxyethyl) isocyanurate triacrylate, pentaerythritol triacrylate, ethoxylated (3) trimethylolpropane triacrylate, propoxylated (3) glycerol triacrylate, pentaerythritol tetraacrylate, bis(trimethylolpropane) tetraacrylate, ethoxylated (4) pentaerythritol tetraacrylate, dipentaerythritol pentaacrylate, 2-(2-ethoxyethoxy)ethyl acrylate, hexanediol diacrylate, polyethylene glycol diacrylate, polyethylene glycol dimethacrylate, tripropylene glycol triacrylate, dipentaerythritol hexaacrylate, ethylene glycol diacrylate, 1,6-hexanediol diacrylate, ethoxylated 1,6-hexanediol diacrylate, polypropylene glycol diacrylate, 1,4-butanediol diacrylate, 1,9-nonanediol diacrylate, tetraethylene glycol diacrylate, 2-n-butyl-2-ethyl-1,3-propanediol diacrylate, hydroxypivalic acid neopentyl glycol diacrylate, hydroxypivalic acid trimethylolpropane triacrylate, ethoxylated trisacrylate phosphate, ethoxylated tripropylene glycol diacrylate, neopentyl glycol-modified trimethylolpropane diacrylate, stearic acid-modified pentaerythritol diacrylate, tetramethylolpropane triacrylate, tetramethylolmethane triacrylate, caprolactone-modified trimethylolpropane triacrylate, propoxylated glycerol triacrylate, tetramethylolmethane tetraacrylate, ethoxylated pentaerythritol tetraacrylate, dipentaerythritol hexaacrylate, caprolactone-modified dipentaerythritol hexaacrylate, dipentaerythritol hydroxypentaacrylate, neopentyl glycol oligoacrylate, trimethylolpropane oligoacrylate, pentaerythritol oligoacrylate, ethoxylated neopentyl glycol di(meth)acrylate, propoxylated neopentyl glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, ethoxylated trimethylolpropane triacrylate, propoxylated trimethylolpropane triacrylate, and 2-(2-vinyloxyethoxy)ethyl acrylate, etc.

[0039] The polyfunctional radically polymerizable compound (A3) particularly preferably contains glycerol triacrylate. Glycerol triacrylate is polyfunctional and has a low viscosity, so that the composition (X) can be made to have a low viscosity. Particularly when the composition (X) is ejected by an inkjet method, the polyfunctional radically polymerizable compound (A3) preferably contains glycerol triacrylate.

[0040] The proportion of the polyfunctional radically polymerizable compound (A3) in the composition (X) is preferably 1% by mass or more and 20% by mass or less with respect to the radically polymerizable compound (A). This proportion is more preferably 2% by mass or more, and further preferably 15% by mass or more. In addition, this proportion is more preferably 3% by mass or less, and further preferably 10% by mass or less.

[0041] The photo-radically polymerizable compound (A) may contain components other than the above within a range that does not significantly hinder the effects of the present embodiment. For example, the photo-radically polymerizable compound (A) may contain a third monofunctional radically polymerizable compound (A4) that has only one radically polymerizable functional group in the molecule and is different from the above-mentioned first monofunctional radically polymerizable compound (A1) and second monofunctional radically polymerizable compound (A2).

[0042] The third monofunctional radically polymerizable compound (A4) contains, for example, at least one compound selected from tetrahydrofurfuryl acrylate, isobornyl acrylate, 2-hydroxyethyl acrylate, 4-hydroxybutyl acrylate, isobutyl acrylate, tert-butyl acrylate, isooctyl acrylate, 2-methoxyethyl acrylate, methoxytriethylene glycol acrylate, 2-ethoxyethyl acrylate, 3-methoxybutyl acrylate, ethoxyethyl acrylate, butoxyethyl acrylate, ethoxydiethylene glycol acrylate, methoxydioxylethyl acrylate (Japanese: メトキシジキシルエチルアクリレート), ethyldiethylene glycol acrylate, cyclic trimethylolpropane formal monoacrylate, imide acrylate, isopentyl acrylate, ethoxylated succinic acid acrylate, trifluoroethyl acrylate, ω-carboxypolycaprolactone monoacrylate, cyclohexyl acrylate, 2-(2-ethoxyethoxy)ethyl acrylate, stearyl acrylate, diethylene glycol monobutyl ether acrylate, lauryl acrylate, isodecyl acrylate, 3,3,5-trimethylcyclohexanol acrylate, isooctyl acrylate, octyl / decyl acrylate, tridecyl acrylate, caprolactone acrylate, ethoxylated (4) nonylphenol acrylate, methoxypolyethylene glycol (350) monoacrylate, methoxypolyethylene glycol (550) monoacrylate, phenoxyethyl acrylate, (meth)cyclohexyl acrylate, (meth)dicyclopentyl acrylate, (meth)tetrahydrofurfuryl acrylate, benzyl acrylate, methylphenoxyethyl acrylate, 4-tert-butylcyclohexyl acrylate, caprolactone-modified tetrahydrofurfuryl acrylate, tribromophenyl acrylate, ethoxylated tribromophenyl acrylate, 2-phenoxyethyl acrylate, ethylene oxide adduct of 2-phenoxyethyl acrylate, propylene oxide adduct of 2-phenoxyethyl acrylate, dicyclopentyl acrylate, phenoxydiethylene glycol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 1,4-cyclohexanedimethanol monoacrylate, 3-methacryloxymethyl epoxyhexane, and 3-acryloxymethyl epoxyhexane.

[0043] The third monofunctional radically polymerizable compound (A4) may contain a monofunctional radically polymerizable compound (A41) that is different from the above-described first monofunctional radically polymerizable compound (A1) and has two or more aromatic rings. This monofunctional radically polymerizable compound (A41) can also increase the refractive index of the cured product. However, in order to suppress breakage of the cured product during deformation and improve the formability of the composition (X), the proportion of the monofunctional radically polymerizable compound (A41) relative to the radically polymerizable compound (A) is preferably 50% by mass or less, more preferably 45% by mass or less, and still more preferably 40% by mass or less.

[0044] The monofunctional radically polymerizable compound (A41) contains, for example, at least one of the compounds represented by the following formula (2) and the compounds represented by the following formula (3).

[0045] [Chemical Formula 3]

[0046]

[0047] [Chemical Formula 4]

[0048]

[0049] In formula (2), X 1 is hydrogen or methyl, Y 1 is a single bond or an alkylene group having 1 to 6 carbon atoms, Z 1 is a single bond, S or O, R 1 is H or methyl, L 1 is a single bond, an ester bond or a thioester bond, n is 1 or 2. Among them, when L 1 is a single bond, n is 1 and m is 6 or 7. In formula (3), X 2 is a single bond or O, Z 2 is a single bond or O, R 2 is H or methyl, Y 2 is a single bond or an alkylene group having 1 to 6 carbon atoms, L 2 is a single bond or an ester bond. Among them, the case where X 2 is a single bond, Z 2 is a single bond, and L 2 is an ester bond is excluded from the compounds represented by formula (3).

[0050] The photo radical polymerization initiator (B) will be described. The photo radical polymerization initiator (B) contains, for example, at least one compound selected from aromatic ketones, acylphosphine oxide compounds, aromatic onium salt compounds, organic peroxides, sulfur compounds (such as thioxanthone compounds, compounds containing thiophenyl, etc.), hexaarylbiimidazole compounds, oxime ester compounds, borate ester compounds, azinium compounds, metallocene compounds, active ester compounds, compounds having a carbon-halogen bond, and alkylamine compounds.

[0051] The proportion of the photo radical polymerization initiator (B) relative to the total of the radical polymerizable compound (A) and the photo radical polymerization initiator (B) is preferably 2% by mass or more. In this case, the composition (X) can have good photocurability and can also have good photocurability in an air atmosphere. This proportion is more preferably 3% by mass or more, and still more preferably 4% by mass or more. In addition, this proportion is, for example, 15% by mass or less, preferably 12% by mass or less, and still more preferably 10% by mass or less.

[0052] The photo radical polymerization initiator (B) may include a photo radical polymerization initiator having photo bleaching properties. In this case, the cured product of the composition (X) may have good light transmittance. The proportion of the photo radical polymerization initiator having photo bleaching properties relative to the total of the radically polymerizable compound (A) and the photo radical polymerization initiator (B) is preferably 1% by mass or more. This proportion is more preferably 2% by mass or more, and further preferably 3% by mass or more. In addition, this proportion is, for example, 12% by mass or less, preferably 10% by mass or less, and further preferably 8% by mass or less.

[0053] The photo radical polymerization initiator having photo bleaching properties contains, for example, at least one of the compounds having photo bleaching properties among acylphosphine oxide-based photoinitiators and oxime ester-based photoinitiators.

[0054] The photo radical polymerization initiator (B) may include 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. That is, the photo radical polymerization initiator (B) preferably includes a component having at least one of a 9H-thioxanthen-9-one skeleton and an anthracene skeleton.

[0055] The photo radical polymerization initiator (B) preferably contains a compound (B1) that is excited by absorbing light with a wavelength of 395 nm. In this case, when the composition (X) is irradiated with ultraviolet light, the reactivity of the composition (X) can be improved. The absorption coefficient of the light with a wavelength of 395 nm of the sample obtained by dissolving the compound (B1) in acetonitrile at a concentration of 0.01 g / L is preferably 0.1 mL / g·cm or more.

[0056] The proportion of the compound (B1) relative to the photo radical polymerization initiator (B) is preferably 40% by mass or more. In this case, when the composition (X) is irradiated with ultraviolet light, the reactivity of the composition (X) can be further improved. This proportion is more preferably 60% by mass or more, and further preferably 80% by mass or more. The upper limit is not particularly specified and may be 100% by mass. That is, this proportion is, for example, 100% by mass or less.

[0057] In the case where the photo-radical polymerization initiator (B) contains the compound (B1), the compound (B1) contains, for example, at least one selected from 2-benzyl-2-(dimethylamino)-1-(4-morpholinophenyl)-1-butanone (for example, Irgacure 369 manufactured by BASF), phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide (for example, Irgacure 819 manufactured by BASF), 2,4,6-trimethylbenzoyl-diphenylphosphine oxide (for example, Omnirad TPO H manufactured by IGM RESINS B.V.), and bis(2,4-cyclopentadienyl)bis[2,6-difluoro-3-(1-pyridyl)phenyl]titanium(IV) (for example, Irgacure 784 manufactured by BASF).

[0058] In addition to the photo-radical polymerization initiator (B), the composition (X) may contain a polymerization accelerator. The polymerization accelerator contains, for example, amine compounds such as ethyl p-dimethylaminobenzoate, 2-ethylhexyl p-dimethylaminobenzoate, methyl p-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, and butoxyethyl p-dimethylaminobenzoate. It should be noted that the components that the polymerization accelerator may contain are not limited to the above components.

[0059] The composition (X) preferably does not contain an inorganic filler. In this case, when changing the cured product of the composition (X), breakage of the cured product can be further suppressed. In addition, in the present embodiment, even without using an inorganic filler to make the cured product have a high refractive index, the refractive index of the cured product can be increased by the first monofunctional radical polymerizable compound (A1) represented by the formula (1).

[0060] The composition (X) may contain an inorganic filler within a range that does not significantly impede the object of the present disclosure. In this case, the proportion of the inorganic filler relative to the composition (X) is preferably 25% by mass or less. This proportion is more preferably 3% by mass or less.

[0061] The composition (X) preferably contains no solvent or contains 1% by mass or less of a solvent. In this case, it is difficult for outgassing gas from the solvent to be generated from the composition (X) and the cured product of the composition (X). In addition, when manufacturing an optical component and a light-emitting device, a drying process for removing the solvent from the composition (X) and the cured product may not be required. 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 a reduction in the heating temperature and a shortening of the heating time in the drying process can be achieved. Therefore, it is possible to prevent outgassing gas from being easily generated from the optical component without reducing the manufacturing efficiency of the optical component and the light-emitting device. Furthermore, particularly in the case of forming by ejecting the composition (X) by an inkjet method, a reduction in thickness due to the volatilization of the solvent from the formed composition (X) is less likely to occur, and thus a reduction in the thickness of the optical component is less likely to occur. Therefore, while forming by ejecting the composition (X) by an inkjet method, it is possible to ensure that the thickness of the optical component is as large as possible. The content of the solvent is more preferably 0.5% by mass or less, further preferably 0.3% by mass or less, and particularly preferably 0.1% by mass or less. Particularly preferably, the composition (X) contains no solvent or contains only an unavoidably mixed solvent.

[0062] The composition (X) may further contain any additives other than those described above within a range that does not significantly impede the object of the present disclosure.

[0063] In the present embodiment, the composition (X) can be used to manufacture an optical component. An optical component is a component disposed on the optical path of light in an optical system. In the present embodiment, the composition (X) can be preferably used to manufacture an optical component that transmits light. However, the use of the composition (X) is not limited to the manufacture of optical components, and the composition (X) can also be applied to various uses that utilize its characteristics.

[0064] The refractive index of the cured product of the composition (X) is preferably 1.58 or more. That is, it is preferable to increase the refractive index of the cured product by using the present embodiment so that the cured product has a refractive index of 1.58 or more. In this case, particularly when an optical component made of the composition (X) is overlapped with an inorganic film in a light-emitting device, the luminous efficiency of the light-emitting device can be particularly improved. The refractive index is more preferably 1.60 or more, and further preferably 1.62 or more. The upper limit of the refractive index is not particularly limited. For example, the refractive index is 1.8 or less, and preferably 1.65 or less. It should be noted that the refractive index in the present disclosure refers to the refractive index of light with a wavelength of 589 nm in an atmosphere at 25°C.

[0065] In the present embodiment, the composition (X) may have a low viscosity. Therefore, the formability of the composition (X) is good. For example, the composition (X) can be ejected by an inkjet method for forming. When producing a cured product or an optical component from the composition (X), it is preferable to eject the composition (X) by an inkjet method for forming. That is, the composition (X) is preferably used for inkjet forming. In this case, a cured product and an optical component of the composition (X) can be produced with good positional accuracy. In addition, when the composition (X) is formed by an inkjet method, foreign matter is less likely to be mixed into the composition (X) and its cured product compared to the case of forming by a printing method accompanied by contact such as a screen printing method. Therefore, the qualified rate when producing an optical component is less likely to deteriorate.

[0066] The viscosity of the composition (X) at 40 °C is preferably 16 mPa·s or less. In this case, regardless of the viscosity of the composition (X) at normal temperature, as long as the composition (X) is slightly heated, its viscosity can be lowered. Therefore, if heating is performed, the composition (X) can be easily formed, and in particular, it can be easily formed by ejecting it by an inkjet method. In addition, the composition (X) can be lowered in viscosity without significantly heating it, so the composition of the composition (X) is less likely to change due to the volatilization of the components in the composition (X). This viscosity is also preferably 1 mPa·s or more, and more preferably 5 mPa·s or more.

[0067] The viscosity of the composition (X) at 25 °C is preferably 35 mPa·s or less. The viscosity of the composition (X) at 25 °C is more preferably 30 mPa·s or less, further preferably 27 mPa·s or less, and particularly preferably 24 mPa·s or less. This viscosity is also preferably 1 mPa·s or more, more preferably 5 mPa·s or more, and also preferably 8 mPa·s or more. In these cases, the composition (X) can be easily formed at normal temperature, and in particular, it can be easily formed by an inkjet method.

[0068] Such a low viscosity of the composition (X) can be achieved by appropriately adjusting the composition of the photo-radical polymerizable compound (A) within the range described above. It should be noted that the measurement method and conditions of the viscosity of the composition (X) are described in detail in the Examples section below.

[0069] The proportion of the evolved gas generated when the cured product of the composition (X) is heated at 110°C for 30 minutes is preferably 25 ppm or less. That is, according to the present embodiment, since the curability of the composition (X) is improved, the proportion of the evolved gas generated from the cured product is preferably 25 ppm or less. In this case, it is difficult for the cured product to generate evolved gas. Therefore, for example, it is possible to make it difficult for voids caused by the evolved gas to be generated in the light-emitting device including the optical component formed of the cured product. Therefore, it is possible to make it difficult for water and oxygen to reach the light-emitting element through the voids, and thus the light-emitting element is not easily deteriorated by water and oxygen. The proportion of the evolved gas is particularly preferably 15 ppm.

[0070] The reduction of the proportion of the evolved gas generated from the cured product of the composition (X) can be achieved by appropriately adjusting the composition of the photo-radical polymerizable compound (A) within the range described above. It should be noted that the method for measuring the proportion of the evolved gas will be described in detail in the examples below.

[0071] The glass transition temperature of the cured product of the composition (X) is preferably 75°C or higher. That is, the composition (X) preferably has the property of becoming a cured product with a glass transition temperature of 75°C or higher through curing. In this case, the cured product can have good heat resistance. Therefore, for example, when a treatment accompanied by a temperature rise is performed on the cured product, the cured product is not easily deteriorated. Therefore, for example, in the case of forming an inorganic film (such as the passivation layer 6) overlapping the optical component by a vapor deposition method such as plasma CVD, even if the optical component is heated, the optical component is not easily deteriorated. In addition, by improving the heat resistance, the optical component can also be made suitable for applications such as in-vehicle use where strict requirements for heat resistance are imposed. The glass transition temperature of the cured product is more preferably 80°C or higher, further preferably 90°C or higher, and particularly preferably 100°C or higher. The glass transition temperature of the cured product can be achieved by appropriately adjusting the composition of the photo-radical polymerizable compound (A) within the range described above.

[0072] An example of the structure of the light-emitting device 1 including the optical component made of the composition (X) will be described. The light-emitting device 1 includes a light source and an optical component that transmits the light emitted by the light source. For example, the light-emitting device 1 includes a light-emitting element 4, a sealing material 5 that covers the light-emitting element 4, and a passivation layer 6. In this case, the light-emitting element 4 is the light source, the sealing material 5 is the optical component, and the passivation layer 6 is the inorganic film. The sealing material 5 overlaps with the passivation layer 6.

[0073] 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. When the light-emitting element 4 includes an organic light-emitting diode, the light-emitting device 1 including the light-emitting element 4 is, for example, an organic EL display. When 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. It should be noted that EL is an abbreviation for electroluminescence.

[0074] Refer to Figure 1 An example of the structure of the light-emitting device 1 will be described. The light-emitting device 1 is a top-emitting type. The light-emitting device 1 includes a support substrate 2, a transparent substrate 3 facing the support substrate 2 at an interval, a light-emitting element 4 located on the surface of the support substrate 2 facing the transparent substrate 3, and a passivation layer 6 and a sealing material 5 covering the light-emitting element 4.

[0075] The support substrate 2 is made of, for example, a resin material, but is not limited thereto. The transparent substrate 3 is made of a light-transmissive 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 located 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.

[0076] The light-emitting device 1 includes a plurality of light-emitting elements 4, and the plurality of light-emitting elements 4 form an array 9 (hereinafter referred to as the element array 9) on the support substrate 2. The element array 9 further includes a partition wall 7. The partition wall 7 is located on the support substrate 2 and separates between two adjacent light-emitting elements 4. The partition wall 7 is made, for example, by forming a photosensitive resin material by photolithography. The element array 9 further includes a connection wiring 8 that electrically connects the electrodes 43 and the electron transport layers 424 of adjacent light-emitting elements 4 to each other. The connection wiring 8 is provided on the partition wall 7.

[0077] The passivation layer 6 corresponds to an inorganic film. The passivation layer 6 is preferably made of silicon nitride or silicon oxide, and particularly preferably made of silicon nitride. In Figure 1 the example shown, 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 in a state of being in direct contact with the element array 9, thereby covering the light-emitting element 4. The second passivation layer 62 is disposed at a position opposite to the element array 9 with respect to the first passivation layer 61, and there is an interval between the second passivation layer 62 and the first passivation layer 61. The sealing material 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 sealing material 5 covering the light-emitting element 4.

[0078] In addition, 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 is no particular limitation 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 that of the sealing material 5.

[0079] A method for producing the sealing material 5 using the composition (X) and a method for manufacturing the light-emitting device 1 will be described.

[0080] In the present embodiment, it is preferable to cure the composition (X) by irradiating ultraviolet rays after ejecting the composition (X) by an inkjet method and forming it into a film shape, thereby producing the sealing material 5. In the present embodiment, the composition (X) can be ejected by an inkjet method and formed.

[0081] When ejecting the composition (X) by an inkjet method, when the composition (X) has a sufficiently low viscosity at room temperature, for example, when the viscosity at 25°C is 30 mPa·s or less, particularly 16 mPa·s or less, the composition (X) can be ejected and formed by an inkjet method without heating the composition (X). When the composition (X) is heated to lower its viscosity, the composition (X) can be ejected by an inkjet method after heating the composition (X). As described above, particularly when the viscosity of the composition (X) at 40°C is 16 mPa·s or less, the composition (X) can be made to have a low viscosity by slightly heating, and the low-viscosity composition (X) can be ejected by an inkjet method. The heating temperature of the composition (X) is, for example, 20°C or higher and 50°C or lower.

[0082] More specifically, for example, first, a support substrate 2 is prepared. On one surface of the support substrate 2, for example, using a photosensitive resin material, the partition walls 7 are formed by photolithography. 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 produced by an appropriate method such as an evaporation method or a coating method. It is particularly preferable to produce the light-emitting elements 4 by a coating method such as an inkjet method. Thus, an element array 9 is produced on the support substrate 2.

[0083] Next, a first passivation layer 61 is provided on the element array 9. The first passivation layer 61 can be produced by an evaporation method such as a plasma CVD method, for example.

[0084] Next, on the first passivation layer 61, for example, the composition (X) is ejected by an inkjet method for forming to produce a coating film. If an inkjet method is applied both in the formation of the light-emitting elements 4 and the formation of the composition (X), the manufacturing efficiency of the light-emitting device 1 can be particularly improved. Next, the coating film of the composition (X) is irradiated with light to cure it, thereby producing the sealing material 5.

[0085] When irradiating the composition (X) with light, the composition (X) can be irradiated with light in an oxygen-containing atmosphere such as an atmospheric atmosphere, or the composition (X) can be irradiated with light in an inert atmosphere such as a nitrogen atmosphere.

[0086] Next, a second passivation layer 62 is provided on the sealing material 5. The second passivation layer 62 can be formed, for example, by a vapor deposition method such as plasma CVD.

[0087] Next, a photocurable resin material is provided on one surface of the support substrate 2 so as to cover the second passivation layer 62, and then the transparent substrate 3 is overlapped on the resin material. The transparent substrate 3 is, for example, a glass substrate or a transparent resin substrate.

[0088] Then, ultraviolet rays are irradiated onto the transparent substrate 3 from the outside. The ultraviolet rays pass through the transparent substrate 3 and reach the photocurable resin material. As a result, the photocurable resin material is cured to produce the second sealing material 52.

[0089] In the present embodiment, as described above, the cured product of the composition (X) can have a high refractive index. Therefore, even when the sealing material 5 overlaps with the passivation layer 6 which is an inorganic film, a reduction in luminous efficiency is not likely to occur.

[0090] The thickness of the sealing material 5 is, for example, 1 μm or more and 50 μm or less. The thickness of the sealing material 5 is more preferably 20 μm or less, and further preferably 15 μm or less. In this case, by thinning the sealing material 5, the light-emitting device 1 can be thinned, and a light-emitting device 1 having flexibility, that is, capable of being bent, can be obtained. In addition, in order to effectively suppress moisture from reaching the light-emitting element 4 by the sealing material 5, the thickness of the sealing material 5 is preferably 3 μm or more, more preferably 5 μm or more, and further preferably 8 μm or more.

[0091] The thickness of the passivation layer 6 overlapping with the sealing material 5 is, for example, 0.1 μm or more and 2 μm or less. As described above, when the passivation layer 6 includes the first passivation layer 61 and the second passivation layer 62, the thicknesses of the first passivation layer 61 and the second passivation layer 62 are each preferably 0.1 μm or more and 2 μm or less.

[0092] It should be noted that the use of the composition (X) in the present embodiment is not limited to manufacturing the sealing material 5 for the light-emitting element 4. The composition (X) can be used to manufacture various optical components that transmit light emitted from a light source. For example, the optical component can be a color resist. That is, for example, a phosphor can be contained in the composition (X), and a color resist in a color filter can be made from the composition (X). The color filter can be provided in, for example, a display device such as an organic EL display or a micro LED display which is a light-emitting device.

[0093] (Summary)

[0094] The photocurable resin composition of the first mode contains a radically polymerizable compound (A) and a photo radical polymerization initiator (B). The radically polymerizable compound (A) contains: a first monofunctional radically polymerizable compound (A1) represented by formula (1), a monofunctional radically polymerizable compound (A2) different from the first monofunctional radically polymerizable compound (A1) and having a nitrogen atom, and a polyfunctional radically polymerizable compound (A3).

[0095] [Chemical formula 5]

[0096]

[0097] In formula (1), R1 is H or CH 3 , X is O or S, and Z is a single bond or a divalent saturated hydrocarbon group.

[0098] According to this mode, the cured product of the photocurable resin composition has a high refractive index and can suppress breakage of the cured product during deformation.

[0099] In the second mode, on the basis of the first mode, the monofunctional radically polymerizable compound (A2) having a nitrogen atom contains at least one selected from 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.

[0100] According to this mode, breakage of the cured product during deformation, particularly in a state where the cured product overlaps an inorganic film, can be further suppressed.

[0101] In the third mode, on the basis of the first or second mode, the photo radical polymerization initiator (B) contains a compound (B1) that is excited by absorbing light with a wavelength of 395 nm.

[0102] According to this mode, the photocurable resin composition can have particularly high ultraviolet curability, and thus gas evolution from the cured product can be suppressed.

[0103] In the fourth mode, on the basis of any one of the first to third modes, the proportion of the first monofunctional radically polymerizable compound (A1) represented by formula (1) is 40% by mass or more and 85% by mass or less with respect to the radically polymerizable compound (A).

[0104] In the fifth mode, on the basis of any one of the first to fourth modes, the proportion of the second monofunctional radically polymerizable compound (A2) is 5% by mass or more and 50% by mass or less with respect to the radically polymerizable compound (A).

[0105] In the sixth mode, based on any one of the first to fifth modes, the viscosity of the photocurable resin composition at 40 °C is 16 mPa·s or less.

[0106] According to this mode, the photocurable resin composition has good formability, and it becomes easy to form by ejecting the photocurable resin composition by an inkjet method.

[0107] In the seventh mode, based on any one of the first to sixth modes, the refractive index of the cured product of the photocurable resin composition is 1.58 or more and 1.65 or less.

[0108] According to this mode, the photocurable resin composition can have a refractive index close to that of an inorganic film.

[0109] In the eighth mode, based on any one of the first to seventh modes, the photocurable resin composition does not contain an inorganic filler.

[0110] According to this mode, breakage during deformation of the cured product can be further suppressed.

[0111] The optical component of the ninth mode includes a cured product of the photocurable resin composition of any one of the first to eighth modes.

[0112] According to this mode, the optical component has a high refractive index and can suppress breakage of the optical component during deformation.

[0113] The method for manufacturing an optical component of the tenth mode includes a step of forming the photocurable resin composition of any one of the first to eighth modes by an inkjet method and then irradiating the photocurable resin composition with light to cure it.

[0114] According to this mode, an optical component can be manufactured with good positional accuracy, and the qualified rate is not likely to deteriorate.

[0115] The light-emitting device (1) of the eleventh mode includes a light source and an optical component that transmits the light emitted by the light source, and the optical component includes a cured product of the photocurable resin composition of any one of the first to eighth modes.

[0116] According to this mode, the optical component of the light-emitting device (1) has a high refractive index and can suppress breakage of the optical component during deformation.

[0117] The method for manufacturing the light-emitting device (1) of the twelfth mode is a method for manufacturing a light-emitting device (1) including a light source and an optical component that transmits the light emitted by the light source, and the method for manufacturing the light-emitting device includes a step of manufacturing the optical component by the method of the tenth mode.

[0118] According to this mode, the optical component in the light-emitting device (1) can be manufactured with good positional accuracy, and the qualified rate is not likely to deteriorate.

[0119] Example

[0120] 1. Preparation of the composition

[0121] The compositions of the examples and comparative examples were prepared by mixing the components shown in the following table. The details of the components shown in the table are as described below. In addition, the "proportion of the first monofunctional compound" in the table is the proportion of the total of the first monofunctional compounds #1 to #3, which are the first monofunctional radically polymerizable compounds, relative to the total amount of the radically polymerizable compounds. In addition, the "proportion of the second monofunctional compound" in the table is the proportion of the total of the second monofunctional compounds #1 to #5, which are the second monofunctional radically polymerizable compounds, relative to the total amount of the radically polymerizable compounds.

[0122] - First monofunctional compound #1: The compound represented by the following chemical formula (11). Manufactured by Kyoeisha Chemical Co., Ltd. Product name: Light Acrylate OPP

[0123] [Chemical formula 6]

[0124]

[0125] - First monofunctional compound #2: The compound represented by the following chemical formula (12). Manufactured by Kyoeisha Chemical Co., Ltd. Product name: Light Acrylate OPP-A.

[0126] [Chemical formula 7]

[0127]

[0128] - First monofunctional compound #3: The compound represented by the following chemical formula (13). Manufactured by Shin-Nakamura Chemical Co., Ltd. Product name: A-BPML.

[0129] [Chemical formula 8]

[0130]

[0131] - Second monofunctional compound #1: Vinyl methyl oxazolidinone. Manufactured by BASF Corporation.

[0132] - Second monofunctional compound #2: Acryloylmorpholine. Manufactured by KJ Chemicals Co., Ltd.

[0133] - Second monofunctional compound #3: Dimethylacrylamide. Manufactured by KJ Chemicals Co., Ltd.

[0134] - Second monofunctional compound #4: Diethylacrylamide. Manufactured by KJ Chemicals Co., Ltd.

[0135] - The 2nd monofunctional compound #5: N-vinyl-2-pyrrolidone. Manufactured by BASF Corporation.

[0136] - The 3rd monofunctional compound #1: The compound represented by the following chemical formula (31). Manufactured by Kyoeisha Chemical Co., Ltd. Product name: OPPEA.

[0137] [Chemical formula 9]

[0138]

[0139] - The 3rd monofunctional compound #2: The compound represented by the following chemical formula (21). Manufactured by Kyoeisha Chemical Co., Ltd. Product name: NMT-A.

[0140] [Chemical formula 10]

[0141]

[0142] - The 3rd monofunctional compound #3: The compound represented by the following chemical formula (32). Manufactured by Kyoeisha Chemical Co., Ltd. Product name: POB-A.

[0143] [Chemical formula 11]

[0144]

[0145] - Polyfunctional compound: Glycerol triacrylate. Manufactured by Toagosei Co., Ltd. Product name: M-930.

[0146] - Initiator #1: 2,4,6-Trimethylbenzoyl-diphenylphosphine oxide. Manufactured by IGM RESINS B.V. Product name: Omnirad TPO H.

[0147] - Initiator #2: Oxime ester-based photo radical polymerization initiator. Manufactured by BASF Japan Ltd. Product name: Irgacure OXE04.

[0148] 2. Evaluation tests

[0149] (1) Refractive index

[0150] A coating film with a thickness of 300 μm was prepared from the coating composition. In a nitrogen atmosphere, a UV irradiator (manufactured by USHIO Inc., model Unijet E075IIHD) was used to irradiate the coating film with light having a peak wavelength of 395 nm under the conditions of an irradiation intensity of 0.5 W / cm 2 and an accumulated light quantity of 1.5 J / cm 2 . Thus, a test sample was prepared. The refractive index of the light with a wavelength of 589 nm of this sample was measured at 25°C in an atmosphere using a multi-wavelength Abbe refractometer (manufactured by ATAGO, model DR-M2).

[0151] (2) Viscosity at 25 °C

[0152] Using a rheometer (manufactured by Anton Paar Japan, model DHR-2), the viscosity of the composition was measured at a temperature of 25 °C and a shear rate of 1000 s -1 .

[0153] (3)Viscosity at 40 °C

[0154] Using a rheometer (manufactured by Anton Paar Japan, model DHR-2), the viscosity of the composition was measured at a temperature of 40 °C and a shear rate of 1000 s -1 .

[0155] (4)Inkjet property

[0156] The composition was added to the ink cartridge of an inkjet printer (manufactured by Fujifilm, model DMP2831), and droplets of the composition were ejected from the nozzle of the inkjet printer at a temperature of 40 °C and a frequency of 1 kHz. The droplets were observed with a high-speed camera. As a result, the case where the droplets did not separate was evaluated as "A", the case where the satellite droplets (Japanese: サテライト) separated from the original droplets and then the satellite droplets and the original droplets merged again to form a single droplet was evaluated as "B", and the case where the satellite droplets remained separated from the original droplets and did not merge was evaluated as "C".

[0157] (5)Curability

[0158] The composition was measured using an infrared spectroscopic analyzer (manufactured by Agilent Technology, model Agilent Cary 610 FTIR microscope system), and an IR spectrum was obtained therefrom.

[0159] The composition was coated to form a film with a thickness of 10 μm. In a nitrogen atmosphere, the film was irradiated with light having a peak wavelength of 395 nm using a UV irradiator (manufactured by USHIO Electric, model Unijet E075IIHD) at an irradiation intensity of 0.5 W / cm 2 and a cumulative light amount of 1.5 J / cm 2 . Subsequently, the composition (cured product) after ultraviolet irradiation was measured using the above infrared spectroscopic analyzer, and an IR spectrum was obtained therefrom.

[0160] In each of the two IR spectra, the absorption peak intensity of the acryloyl group appearing at 810 cm -1 was measured. Based on the peak intensity I 0 of the film and the peak intensity I 1 of the cured product, using {1 - (I 0-I 1 ) / I 0 The reduction rate of the reactive functional groups in the composition before and after ultraviolet irradiation is calculated by the formula of {(

[0161] (6)Evaluation of evolved gas

[0162] The evolved gas during the curing of the heated composition is sampled by the headspace method and measured by a gas chromatograph. Specifically, first, 100 mg of the composition is placed in a vial with a headspace volume of 22 mL. Then, under a nitrogen atmosphere, the composition is irradiated with light having a peak wavelength of 395 nm at an irradiation intensity of 0.5 W / cm 2 and an accumulated light amount of 1.5 J / cm 2 to cure the composition, and then the vial is sealed. Next, after heating the composition at 110 °C for 30 minutes, the gas phase part in the vial is introduced into the gas chromatograph for analysis. As a result, based on the peak area of the obtained gas chromatogram, the concentration of the evolved gas generated by the composition is determined. The concentration of the evolved gas refers to the volume fraction of the evolved gas in the gas phase of the vial relative to the volume of the vial (22 mL).

[0163] It should be noted that the concentration of the evolved gas is determined with toluene as the reference substance. Specifically, by volatilizing toluene in the vial, two reference samples with toluene concentrations of 1000 ppm and 100 ppm are prepared. Each reference sample is introduced into the gas chromatograph for analysis. According to the peak areas of the two chromatograms obtained therefrom, the relationship between the peak area and the concentration is specified, and based on this result, the concentration of the above-mentioned evolved gas is determined.

[0164] The results are evaluated as follows.

[0165] A: The concentration is 15 ppm or less.

[0166] B: The concentration exceeds 15 ppm and is 50 ppm or less.

[0167] C: The concentration exceeds 50 ppm.

[0168] (7)Sealability

[0169] The film is formed by CVD to a thickness of 1 μm, thereby forming a silicon oxynitride film (SiON film) as an inorganic film on a glass slide. A composition is coated on the inorganic film to a thickness of 10 μm to form a coating film. In a nitrogen atmosphere, the coating film is irradiated with light having a peak wavelength of 395 nm using a UV irradiator (manufactured by USHIO, model Unijet E075IIHD) at an irradiation intensity of 0.5 W / cm 2 and an accumulated light quantity of 1.5 J / cm 2 under the conditions. The coating film is stretched along the 90-degree direction using an Autograph (manufactured by Shimadzu Corporation, model AGS-X), and the peel strength is measured. When the peel strength is 100 mN / cm or more, it is evaluated as "A". When the peel strength is 50 mN / cm or more, it is evaluated as "B". When the peel strength is 20 mN / cm or more, it is evaluated as "C". When the peel strength is less than 20 mN / cm, it is evaluated as "D".

[0170] (8)Flexibility

[0171] By CVD, a silicon oxynitride film (SiON film) as an inorganic film is formed on a polyimide film as a substrate to a thickness of 1 μm. A composition is coated on the inorganic film to a thickness of 10 μm to form a coating film. In a nitrogen atmosphere, the coating film is irradiated with light having a peak wavelength of 395 nm using a UV irradiator (manufactured by USHIO, model Unijet E075IIHD) at an irradiation intensity of 0.5 W / cm 2 and an accumulated light quantity of 1.5 J / cm 2 under the conditions, thereby producing a film with a thickness of 10 μm. Thus, an evaluation sample having a substrate, an inorganic film, and a film is produced.

[0172] The evaluation sample was subjected to a test of repeatedly bending it 100,000 times under the conditions where the radius of curvature of the bending part was 1.5 mm, 2.0 mm, and 5.0 mm.

[0173] As a result, when the film in the evaluation sample after the test under any condition did not peel or break, it was evaluated as "A". When the film did not peel or break after the test under the conditions of a bending radius of 2.0 mm and 5.0 mm but peeled or broke under the condition of 1.5 mm, it was evaluated as "B". When the film did not peel or break after the test under the condition of a bending radius of 5.0 mm but peeled or broke under the conditions of 1.5 mm and 2.0 mm, it was evaluated as "C". When the film peeled or broke under any condition after the test, it was evaluated as "D".

[0174] (9)Glass transition temperature

[0175] A coating composition was used to form a coating film. In an atmospheric atmosphere, a UV irradiator (manufactured by USHIO Inc., model E075IIHD) was used to irradiate the coating film with light having a peak wavelength of 395 nm at an irradiation intensity of 3 W / cm 2 and an accumulated light quantity of 15 J / cm 2 to photocure the coating film, and a film with a thickness of 500 μm was produced. A viscoelasticity measuring device (manufactured by Hitachi High-Tech Science Corporation, model DMA7100) was used to measure the glass transition temperature of a sample cut from the film.

[0176] [Table 1]

[0177]

[0178] [Table 2]

[0179]

[0180] [Table 3]

[0181]

[0182] Explanation of Reference Numerals

[0183] 1 Light-emitting device

[0184] 4 Light-emitting element (light source)

[0185] 5 Sealing material (optical component)

Claims

1. A photocurable resin composition containing a radically polymerizable compound (A) and a photo-radical polymerization initiator (B). The radically polymerizable compound (A) contains: A first monofunctional radically polymerizable compound (A1) represented by formula (1); A second monofunctional radically polymerizable compound (A2) different from the first monofunctional radically polymerizable compound (A1) and having a nitrogen atom; and A polyfunctional radically polymerizable compound (A3). In formula (1), R1 is H or CH 3 , X is O or S, and Z is a single bond or a divalent saturated hydrocarbon group.

2. The photocurable resin composition according to claim 1, wherein The monofunctional radically polymerizable compound (A2) having a nitrogen atom contains at least one selected from 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.

3. The photocurable resin composition according to claim 1, wherein The photo-radical polymerization initiator (B) contains a compound (B1) that is excited by absorbing light with a wavelength of 395 nm.

4. The photocurable resin composition according to claim 1, wherein Relative to the radically polymerizable compound (A), the proportion of the first monofunctional radically polymerizable compound (A1) represented by formula (1) is 40% by mass or more and 85% by mass or less.

5. The photocurable resin composition according to claim 1, wherein Relative to the radically polymerizable compound (A), the proportion of the second monofunctional radically polymerizable compound (A2) is 5% by mass or more and 50% by mass or less.

6. The photocurable resin composition according to claim 1, wherein The viscosity of the photocurable resin composition at 40 °C is 16 mPa·s or less.

7. The photocurable resin composition according to claim 1, wherein The refractive index of the cured product of the photocurable resin composition is 1.58 or more and 1.65 or less.

8. The photocurable resin composition according to claim 1 does not contain an inorganic filler.

9. An optical component comprising a cured product of the photocurable resin composition according to any one of claims 1 to 8.

10. A method for manufacturing an optical component, which includes forming the photocurable resin composition according to any one of claims 1 to 8 by an inkjet method and then irradiating the photocurable resin composition with light to cure it.

11. A light-emitting device having a light source and an optical component that transmits the light emitted by the light source, and the optical component comprises a cured product of the photocurable resin composition according to any one of claims 1 to 8.

12. A method for manufacturing a light-emitting device, which is a method for manufacturing a light-emitting device having a light source and an optical component that transmits the light emitted by the light source, The method for manufacturing the light-emitting device includes a step of manufacturing the optical component by the method according to claim 10.

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