Photocurable resin composition, method for manufacturing optical component, and light emitting device

Abstract

This photocurable resin composition contains a photopolymerizable compound (A) and a photopolymerization initiator (B). The photopolymerizable compound (A) contains a sulfur-containing monomer (A1) that contains 10 mass% or more of sulfur atoms in each molecule. The photocurable resin composition is in a liquid state.

Description

Photocurable resin composition, method for manufacturing optical component, and light-emitting device

[0001] The present disclosure generally relates to a photocurable resin composition, a method for producing an optical component, and a light-emitting device, and more particularly to a photocurable resin composition containing a photopolymerizable compound, a method for producing an optical component, and a light-emitting device.

[0002] Patent Literature 1 discloses an organic light-emitting diode display device including a substrate having an active region and a non-active region, a light-emitting diode arranged in the active region, an encapsulation layer on the light-emitting diode, and a passivation layer having at least one lens pattern having a convex shape on the encapsulation layer and a first opening covering the at least one lens pattern in the active region and the non-active region and exposing a first pad region. The patent Literature 1 discloses that the lens pattern is formed by photolithography, and that the convex shape is formed by removing the edges of the lens formed by photolithography.

[0003] US Patent Application Publication No. 2022 / 0199957

[0004] In conventional microlens manufacturing methods, when lenses are fabricated by photolithography, there is a problem in that unnecessary material cannot be completely removed by development, but no suitable material has been provided to solve this problem.

[0005] The object of the present disclosure is to provide a photocurable resin composition that has a moderately high refractive index when cured and that can moderately suppress wettability when applied to an inorganic material, a method for manufacturing an optical component, and a light-emitting device.

[0006] A photocurable resin composition according to one embodiment of the present disclosure includes a photopolymerizable compound (A) and a photopolymerization initiator (B). The photopolymerizable compound (A) includes a sulfur-containing monomer (A1) containing 10% by mass or more of sulfur atoms per molecule. The photocurable resin composition is in a liquid state.

[0007] A method for manufacturing an optical component according to one aspect of the present disclosure includes ejecting the photocurable resin composition by an inkjet method, and then irradiating the photocurable resin composition with light to cure it, thereby manufacturing an optical component.

[0008] A light-emitting device according to one aspect of the present disclosure includes a support substrate, a light-emitting element disposed on the support substrate, a sealing layer disposed on the light-emitting element, and a microlens disposed on the sealing layer, wherein the microlens includes a cured product of the photocurable resin composition.

[0009] FIG. 1 is a schematic cross-sectional view showing a light-emitting device according to an embodiment of the present disclosure.

[0010] An embodiment of the present disclosure will be described with reference to FIG. 1 . Note that the following embodiment is merely a portion of various embodiments of the present disclosure. Furthermore, various modifications to the following embodiment are possible 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 arrows indicating each direction in the figures are not intended to define the direction when the light-emitting device 1 is in use, but are merely depicted to make the explanation easier to understand and have no substance. The first direction D1 and the second direction D2 are mutually orthogonal. The first direction D1 is the direction in which the multiple microlenses 10 are arranged. The second direction D2 is the direction in which the support substrate 2, the light-emitting element 4, the sealing layer 5, and the microlenses 10 overlap, and is orthogonal to the first direction D1. Furthermore, the mechanism of action described below is speculation, and the present disclosure is not bound by the explanation of the mechanism of action below. In the following description, "(meth)acryl" is a generic term that is a broader concept of "acryl" and "methacryl," and refers to "acryl" or "methacryl," or "acryl" and "methacryl." For example, "(meth)acryloyl group" refers to an acryloyl group or a methacryloyl group, or an acryloyl group and a methacryloyl group.

[0011] 1. Overview A photocurable resin composition according to an embodiment (hereinafter also referred to as composition (X)) contains a photopolymerizable compound (A) and a photopolymerization initiator (B). The photopolymerizable compound (A) contains a sulfur-containing monomer (A1) containing 10% by mass or more of sulfur atoms per molecule. The composition (X) is liquid.

[0012] According to the above-mentioned configuration, the cured product has a high refractive index, and the wettability of the composition (X) when applied to an inorganic material can be appropriately suppressed.

[0013] Because the wettability of composition (X) when applied to an inorganic material can be appropriately suppressed, when droplets of composition (X) are deposited on the inorganic material, the droplets are less likely to spread and can have a convex curved surface with an appropriately small radius of curvature. Therefore, simply by curing the droplets, a cured product in the shape of a minute convex lens can be formed. Furthermore, since the cured product can have a high refractive index, it can be suitably applied to optical components such as microlenses 10 (see FIG. 1). Optical components are components that have the function of transmitting light. The optical component according to the embodiment is a microlens 10. In other words, composition (X) according to the embodiment can also be said to be for use in producing microlenses.

[0014] In this way, by using composition (X), minute microlenses 10 can be produced with fewer steps than when the microlenses 10 are produced by photolithography. Furthermore, when the microlenses 10 are produced by photolithography, it is sometimes the case that unnecessary material cannot be completely removed by development, but this does not happen in the embodiment. Furthermore, in the process of producing the microlenses 10, there is no need to heat the microlenses 10 to form a convex lens, so that thermal loads are less likely to be imposed on components such as the light-emitting element 4.

[0015] The optical component can also be applied to a light-emitting device. Specifically, when manufacturing a light-emitting device including a light-emitting element and an optical component that transmits light emitted by the light-emitting element, the composition (X) can be used to manufacture the optical component. For example, the light-emitting device is an organic EL light-emitting device. Note that EL stands for electroluminescence, and an organic EL light-emitting device is a light-emitting device that includes an organic EL element (organic light-emitting diode) as a light source. The light-emitting device can also include display devices such as displays. Note that the light-emitting device 1 according to the embodiment includes a support substrate 2, a light-emitting element 4 disposed on the support substrate 2, a sealing layer 5 disposed on the light-emitting element 4, and a microlens 10 disposed on the sealing layer 5. The microlens 10 includes a cured product of the composition (X) (see FIG. 1 ).

[0016] 2. Photocurable Resin Composition The photocurable resin composition according to this embodiment will be described.

[0017] 2.1 Composition As described above, composition (X) contains a photopolymerizable compound (A) and a photopolymerization initiator (B). When composition (X) is irradiated with light, the photopolymerization initiator (B) decomposes, initiating a photoradical polymerization reaction and curing the photopolymerizable compound (A), thereby producing a cured product. The components of composition (X) are described in more detail below.

[0018] (Photopolymerizable Compound) As described above, the composition (X) contains the photopolymerizable compound (A).

[0019] The viscosity of the photopolymerizable compound (A) at 25°C is preferably 40 mPa·s or less. In this case, the viscosity of the composition (X) at room temperature can be particularly reduced. This viscosity is more preferably 35 mPa·s or less, and even more preferably 30 mPa·s or less. Furthermore, the viscosity of the photopolymerizable compound (A) at 25°C is, for example, 1 mPa·s or more.

[0020] The viscosity of the photopolymerizable compound (A) at 40°C is preferably 30 mPa·s or less. In this case, the viscosity of the composition (X) in a heated state can be particularly reduced. This viscosity is more preferably 25 mPa·s or less, and even more preferably 20 mPa·s or less. The viscosity of the photopolymerizable compound (A) at 40°C is, for example, 1 mPa·s or more.

[0021] The components that the photopolymerizable compound (A) may contain are described below. The photopolymerizable compound (A) contains a sulfur-containing monomer (A1) containing 10% by mass or more of sulfur atoms per molecule. This appropriately increases the refractive index of the cured product and makes it easier to suppress the wettability of the composition (X) when applied to an inorganic material.

[0022] The photopolymerizable compound (A) may contain a monomer other than the sulfur-containing monomer (A1) that contains less than 10% by weight of sulfur atoms per molecule, as long as the effects of the present disclosure are not impaired. Examples of the monomer containing less than 10% by weight of sulfur atoms per molecule include at least one selected from the group consisting of 8-(allylthio)-1,3-dimethyl-7-(3-methylbenzyl)-3,7-dihydro-1H-purine-2,6-dione, 2-(allylthio)-1-(phenoxyacetyl)-1H-benzimidazole, and 18-carboxy-1-octadecanethioethylene. Such a monomer containing less than 10% by weight of sulfur atoms per molecule may be included in the radical polymerizable compound (A2) or photopolymerizable compound (A3) described below.

[0023] <Sulfur-containing monomer> As described above, the photopolymerizable compound (A) contains a sulfur-containing monomer (A1). The sulfur-containing monomer (A1) preferably contains 15% by mass or more, more preferably 20% by mass or more, of sulfur atoms per molecule. The sulfur-containing monomer (A1) may also contain 60% by mass or less of sulfur atoms per molecule. In this case, bonds between sulfur atoms or bonds between sulfur atoms and atoms other than sulfur atoms are broken under high-temperature loading, which prevents deterioration of mechanical properties and optical properties and improves the heat resistance of the cured product.

[0024] The sulfur-containing monomer (A1) has a reactive functional group. Examples of the reactive functional group include a (meth)acrylic group, a vinyl group, and an allyl group, with a (meth)acrylic group being preferred. The number of reactive functional groups contained in one molecule of the sulfur-containing monomer (A1) is not particularly limited, and may be one or two or more. In other words, the sulfur-containing monomer (A1) may contain at least one selected from the group consisting of monofunctional monomers, polyfunctional monomers, and the like.

[0025] The sulfur-containing monomer (A1) preferably has an aromatic ring. That is, the sulfur-containing monomer (A1) preferably contains a monomer (hereinafter also referred to as sulfur-containing monomer (A11)) containing 10% by mass or more of sulfur atoms per molecule and having an aromatic ring. In this case, the glass transition temperature and refractive index of the cured product can be increased. Examples of the aromatic ring include aromatic hydrocarbon rings such as benzene ring, naphthalene ring, and anthracene ring, aromatic heterocycles such as thiophene ring, furan ring, pyrrole ring, imidazole ring, triazole ring, and pyridine ring, and condensed rings thereof. Among these, the aromatic ring of the sulfur-containing monomer (A11) is preferably a benzene ring, naphthalene ring, or pyridine ring. The aromatic ring of the sulfur-containing monomer (A11) may have a substituent. The sulfur-containing monomer (A11) may have only one aromatic ring, or two or more aromatic rings.

[0026] Furthermore, the sulfur-containing monomer (A11) more preferably contains a sulfur-containing monomer containing 20% ​​by mass or more of aromatic rings per molecule (hereinafter also referred to as sulfur-containing monomer (A111)). In this case, the glass transition temperature and refractive index of the cured product can be further increased. The mass of the aromatic rings contained in the sulfur-containing monomer (A111) refers to the ratio of the total mass of atoms contained in the aromatic rings. For example, the aromatic rings contained in the sulfur-containing monomer (A111) may also contain heterocycles. In the case of heterocycles, the mass of atoms other than carbon atoms is also included in the ratio of the mass of the aromatic rings contained in the sulfur-containing monomer (A111). Examples of atoms other than carbon atoms include heteroatoms such as nitrogen atoms, oxygen atoms, and sulfur atoms. Furthermore, hydrogen atoms or substituents may be bonded to atoms constituting the skeleton of the aromatic ring, but these hydrogen atoms or substituents are not included in the ratio of the mass of the aromatic rings contained in the sulfur-containing monomer (A111). The sulfur-containing monomer (A111) preferably contains 25% by mass or more, and even more preferably 30% by mass or more, of aromatic rings per molecule, and may contain 60% by mass or less of aromatic rings per molecule, which makes it easier to maintain the elevated glass transition temperature and refractive index of the cured product.

[0027] The sulfur-containing monomer (A1) includes, for example, at least one selected from the group consisting of bis(4-methacryloylthiophenyl)sulfide, 2-(2-pyridinyldithio)ethyl methacrylate, phenylthioethyl acrylate, bis(4-vinylthiophenyl)sulfide, naphthalenylthioethyl acrylate, 2-vinylthiophene, ethyl vinyl sulfide, phenyl vinyl sulfide, and 2-methacryloyloxyethyl thioctic acid. Among these, the sulfur-containing monomer (A1) preferably includes at least one selected from the group consisting of bis(4-methacryloylthiophenyl)sulfide, 2-(2-pyridinyldithio)ethyl methacrylate, phenylthioethyl acrylate, bis(4-vinylthiophenyl)sulfide, and naphthalenylthioethyl acrylate. In this case, when the composition (X) is applied to an inorganic material, it is possible to achieve an appropriate suppression of wettability, an improvement in the glass transition temperature of the cured product, and an appropriately high refractive index of the cured product.

[0028] The content of the sulfur-containing monomer (A1) is preferably 15% by mass or more relative to the photopolymerizable compound (A). In this case, the wettability of the composition (X) when applied to an inorganic material can be more appropriately suppressed. This content is more preferably 25% by mass or more, and even more preferably 35% by mass or more. The upper limit of this content is, for example, 98% by mass or less.

[0029] <Radical Polymerizable Compound> The photopolymerizable compound (A) may contain, in addition to the sulfur-containing monomer (A1), a radical polymerizable compound (A2) other than the sulfur-containing monomer (A1). The radical polymerizable compound (A2) has a reactive functional group. Examples of the reactive functional group include a (meth)acrylic group, a vinyl group, and an allyl group.

[0030] <<Aromatic Ring-Containing (Meth)acrylic Compound>> The radically polymerizable compound (A2) may contain an aromatic ring-containing (meth)acrylic compound (A21) from the viewpoint of adjusting the refractive index and improving the glass transition temperature of the cured product. The molecular form of the aromatic ring-containing (meth)acrylic compound (A21) is not particularly limited, but is at least one selected from the group consisting of a monomer, an oligomer, a prepolymer, and a polymer. Among these, the molecular form is preferably at least one selected from the group consisting of a monomer and an oligomer from the viewpoint of suppressing the viscosity of the composition (X) and improving inkjet properties.

[0031] The content of the aromatic ring-containing (meth)acrylic compound (A21) relative to the photopolymerizable compound (A) is preferably 10% by mass or more, more preferably 15% by mass or more, and even more preferably 20% by mass or more. The content of the aromatic ring-containing (meth)acrylic compound (A21) relative to the photopolymerizable compound (A) is preferably 80% by mass or less, more preferably 70% by mass or less, and even more preferably 60% by mass or less.

[0032] Furthermore, when the sulfur-containing monomer (A1) contains a sulfur-containing monomer (A11), the total content of the sulfur-containing monomer (A11) and the aromatic ring-containing (meth)acrylic compound (A21) relative to the photopolymerizable compound (A) is preferably 50% by mass or more, more preferably 60% by mass or more, and even more preferably 70% by mass or more. The total content of the sulfur-containing monomer (A11) and the aromatic ring-containing (meth)acrylic compound (A21) relative to the photopolymerizable compound (A) is preferably 99% by mass or less, more preferably 98% by mass or less, and even more preferably 97% by mass or less.

[0033] The sulfur-containing monomer (A1) does not overlap with the aromatic ring-containing (meth)acrylic compound (A21). For example, a (meth)acrylic compound having an aromatic ring but containing 10% by mass or more of sulfur atoms per molecule is included in the sulfur-containing monomer (A11).

[0034] The aromatic ring-containing (meth)acrylic compound (A21) includes at least one selected from the group consisting of, for example, phenyl (meth)acrylate, benzyl (meth)acrylate, phenoxyethyl (meth)acrylate, phenoxypropyl (meth)acrylate, EO-modified phenol (meth)acrylate, phenoxydiethylene glycol (meth)acrylate, EO-modified nonylphenol (meth)acrylate, phenyl glycidyl ether (meth)acrylate, phenoxyhydroxypropyl (meth)acrylate, naphthyl (meth)acrylate, naphthylmethyl (meth)acrylate, EO-modified bisphenol A di(meth)acrylate, and EO-modified bisphenol F di(meth)acrylate.

[0035] <<Polyfunctional (meth)acrylic Compound>> The radically polymerizable compound (A2) may contain a polyfunctional (meth)acrylic compound (A22) from the viewpoint of adjusting the refractive index of the cured product. Furthermore, the polyfunctional (meth)acrylic compound (A22) can increase the crosslink density of the cured product. Therefore, the glass transition temperature of the cured product can be increased. The molecular form of the polyfunctional (meth)acrylic compound (A22) is not particularly limited, but is at least one selected from the group consisting of a monomer, an oligomer, a prepolymer, and a polymer. Among these, the molecular form is preferably at least one selected from the group consisting of a monomer and an oligomer from the viewpoint of suppressing the viscosity of the composition (X) and improving inkjet properties. The polyfunctional (meth)acrylic compound (A22) does not overlap with the sulfur-containing monomer (A1) and the aromatic ring-containing (meth)acrylic compound (A21). For example, a polyfunctional (meth)acrylic compound containing 10% or more sulfur atoms per molecule is included in the sulfur-containing monomer (A1). Furthermore, compounds which are polyfunctional (meth)acrylic compounds but have an aromatic ring and contain less than 10% by mass of sulfur atoms per molecule are included in the aromatic ring-containing (meth)acrylic compounds (A21).

[0036] The content of the polyfunctional (meth)acrylic compound (A22) relative to the photopolymerizable compound (A) is preferably 1% by mass or more, more preferably 2% by mass or more, and even more preferably 3% by mass or more. The content of the polyfunctional (meth)acrylic compound (A22) relative to the photopolymerizable compound (A) is preferably 20% by mass or less, more preferably 15% by mass or less, and even more preferably 10% by mass or less.

[0037] Furthermore, when the sulfur-containing monomer (A1) contains a polyfunctional monomer, the total content of the polyfunctional monomer and the polyfunctional (meth)acrylic compound (A22) contained in the sulfur-containing monomer (A1) relative to the photopolymerizable compound (A) is preferably 10% by mass or more, more preferably 15% by mass or more, and even more preferably 20% by mass or more. The total content of the polyfunctional monomer and the polyfunctional (meth)acrylic compound (A22) contained in the sulfur-containing monomer (A1) relative to the photopolymerizable compound (A) is preferably 60% by mass or less, more preferably 50% by mass or less, and even more preferably 40% by mass or less.

[0038] The polyfunctional (meth)acrylic compound (A22) includes, for example, at least one compound selected from the group consisting of di(meth)acrylic acid esters of alkylene glycols, di(meth)acrylic acid esters of polyalkylene glycols, and (meth)acrylic acid esters of polyols. Examples of di(meth)acrylic acid esters of alkylene glycols include ethylene glycol di(meth)acrylate, 1,4-butanediol di(meth)acrylate, 1,3-butanediol di(meth)acrylate, 1,5-pentanediol di(meth)acrylate, neopentyl glycol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,7-heptanediol di(meth)acrylate, 1,8-hexanediol di(meth)acrylate, 1,9-hexanediol di(meth)acrylate, 2,10-hexanediol di(meth)acrylate, 2,11-hexanediol di(meth)acrylate, 2,12-hexanediol di(meth)acrylate, 2,13-hexanediol di(meth)acrylate, 2,14-hexanediol di(meth)acrylate, 2,15-hexanediol di(meth)acrylate, 2,16-hexanediol di(meth)acrylate, 2,17-hexanediol di(meth)acrylate, 2,18-hexanediol di(meth)acrylate, 2,19-hexanediol di(meth)acrylate, 2,20-hexanediol di(meth)acrylate, 2,21-hexanediol di(meth)acrylate, 2,22-hexanediol di(meth)acrylate, 2,23-hexanediol di(meth)acrylate, 2,24-hexanediol di(meth)acrylate, 2,25-hexanediol di(meth)acrylate, 2,26-hexanediol di(meth)acrylate, 2,27-hexanediol di(meth)acrylate, 2,28-hexanediol di(meth)acrylate, 2,29-hexanediol di(meth)acrylate ,8-octanediol di(meth)acrylate, 1,9-nonanediol di(meth)acrylate, 1,10-decanediol di(meth)acrylate, 1,11-undecanediol di(meth)acrylate, 1,12-dodecanediol di(meth)acrylate, 1,13-tridecanediol di(meth)acrylate, 1,14-tetradecanediol di(meth)acrylate, 1,15-pentadecanediol di(meth)acrylate Acrylate, 1,16-hexadecanediol di(meth)acrylate, 1,17-heptadecanediol di(meth)acrylate, 1,18-octadecanediol di(meth)acrylate, 1,19-nonadecanediol di(meth)acrylate, 1,20-icosanediol di(meth)acrylate, 1,21-heneicosanediol di(meth)acrylate, 1,22-docosanediol di(meth)acrylate, 1,2 The composition contains at least one compound selected from the group consisting of 3-triicosanediol di(meth)acrylate, 1,24-tetracosanediol di(meth)acrylate, 1,25-pentacosanediol di(meth)acrylate, cyclohexanedimethanol di(meth)acrylate, tricyclodecanedimethanol di(meth)acrylate, and 2-n-butyl-2-ethyl-1,3-propanediol di(meth)acrylate.

[0039] The di(meth)acrylic acid ester of polyalkylene glycol contains at least one compound selected from the group consisting of diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, hexaethylene glycol di(meth)acrylate, dipropylene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, tetramethylene glycol di(meth)acrylate, polyethylene glycol di(meth)acrylate, and polypropylene glycol di(meth)acrylate.

[0040] The (meth)acrylic acid ester of polyol includes, for example, at least one selected from the group consisting of trimethylolpropane tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, and dipentaerythritol hexa(meth)acrylate.

[0041] In addition to the compounds listed above, the polyfunctional (meth)acrylic compound (A22) may also be, for example, propoxylated (2) neopentyl glycol di(meth)acrylate, tris(2-hydroxyethyl)isocyanurate tri(meth)acrylate, ethoxylated (3) trimethylolpropane tri(meth)acrylate, propoxylated (3) glyceryl tri(meth)acrylate, ditrimethylolpropane tetra(meth)acrylate, ethoxylated (4) pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, ester, ethoxylated 1,6-hexanediol di(meth)acrylate, neopentyl glycol hydroxypivalate di(meth)acrylate, trimethylolpropane hydroxypivalate tri(meth)acrylate, ethoxylated phosphoric acid tri(meth)acrylate, ethoxylated tripropylene glycol di(meth)acrylate, neopentyl glycol-modified trimethylolpropane di(meth)acrylate, and stearic acid-modified pentaerythritol di(meth)acrylate.

[0042] <<Aliphatic Monofunctional (Meth)acrylic Compound>> The radically polymerizable compound (A2) may contain an aliphatic monofunctional (meth)acrylic compound (A23) from the viewpoint of adjusting the refractive index of the cured product. Furthermore, the aliphatic monofunctional (meth)acrylic compound (A23) has only one radically polymerizable functional group per molecule. Therefore, it is less likely to increase cure shrinkage during curing of the composition (X) and to cause a decrease in adhesion between the inorganic material and the cured product. Furthermore, the aliphatic monofunctional (meth)acrylic compound (A23) can suppress an increase in viscosity of the composition (X). The molecular form of the aliphatic monofunctional (meth)acrylic compound (A23) is not particularly limited, but is at least one selected from the group consisting of a monomer, an oligomer, a prepolymer, and a polymer. Among these, the molecular form is preferably at least one selected from the group consisting of a monomer and an oligomer from the viewpoint of suppressing the viscosity of the composition (X) and improving inkjet performance. The aliphatic monofunctional (meth)acrylic compound (A4) does not overlap with the sulfur-containing monomer (A1), and therefore, a monomer that is an aliphatic monofunctional (meth)acrylic compound but contains 10% by mass or more of sulfur atoms per molecule is included in the sulfur-containing monomer (A1).

[0043] The aliphatic monofunctional (meth)acrylic compound (A23) has, for example, a chain saturated hydrocarbon skeleton having 6 to 20 carbon atoms per molecule. In this case, the flexibility of the cured product can be increased. The chain saturated hydrocarbon skeleton preferably has 8 or more carbon atoms, and more preferably 10 or more carbon atoms. The chain saturated hydrocarbon skeleton preferably has 18 or less carbon atoms, and even more preferably 16 or less carbon atoms.

[0044] The aliphatic monofunctional (meth)acrylic compound (A23) includes at least one selected from the group consisting of, for example, lauryl (meth)acrylate, isostearyl (meth)acrylate, isooctyl (meth)acrylate, isoamyl (meth)acrylate, stearyl (meth)acrylate, isostearyl (meth)acrylate, isodecyl (meth)acrylate, cetyl (meth)acrylate, and tridecyl (meth)acrylate.

[0045] The radically polymerizable compound (A2) may include a compound (hereinafter also referred to as radically polymerizable compound (A24)) having radical polymerizability different from the aromatic ring-containing (meth)acrylic compound (A21), polyfunctional (meth)acrylic compound (A22), and aliphatic monofunctional (meth)acrylic compound (A23) described above. The radically polymerizable compound (A24) includes at least one compound selected from the group consisting of polyfunctional radically polymerizable compounds (A241) having two or more radically polymerizable functional groups per molecule and monofunctional radically polymerizable compounds (A242) having only one radically polymerizable functional group per molecule. The polyfunctional radically polymerizable compound (A241) includes, for example, at least one compound selected from the group consisting of aromatic urethane oligomers, aliphatic urethane oligomers, and other special oligomers having two or more ethylenic double bonds per molecule. The monofunctional radically polymerizable compound (A242) includes, for example, at least one compound selected from the group consisting of phenyl glycidyl ether, p-tert-butylphenyl glycidyl ether, butyl glycidyl ether, 2-ethylhexyl glycidyl ether, allyl glycidyl ether, 1,2-butylene oxide, 1,3-butadiene monoxide, 1,2-epoxydodecane, epichlorohydrin, 1,2-epoxydecane, styrene oxide, cyclohexene oxide, 3-vinylcyclohexene oxide, and 4-vinylcyclohexene oxide.

[0046] <Photopolymerizable Compounds Other Than the Above> The photopolymerizable compound (A) preferably does not contain a photopolymerizable compound containing at least one selected from the group consisting of nitrogen atoms and silicon atoms in one molecule (hereinafter also referred to as photopolymerizable compound (A3)). Even if the photopolymerizable compound (A) contains the photopolymerizable compound (A3), the content of the photopolymerizable compound (A3) relative to the photopolymerizable compound (A) is preferably low. When the photopolymerizable compound (A) contains the photopolymerizable compound (A3), the content of the photopolymerizable compound (A3) relative to the photopolymerizable compound (A) is preferably 10% by mass or less. In this case, the wettability of the composition (X) when applied to an inorganic material can be easily suppressed. This makes it difficult for droplets of the composition (X) to spread and tends to form a convex curved surface with a moderately small radius of curvature.

[0047] The photopolymerizable compound (A3) has a reactive functional group, such as a (meth)acrylic group, a vinyl group, or an allyl group.

[0048] The photopolymerizable compound (A3) is a compound different from the sulfur-containing monomer (A1) and the radically polymerizable compound (A2), and these compounds do not overlap. For example, a compound containing at least one selected from the group consisting of a nitrogen atom and a silicon atom in one molecule and containing less than 10 mass% of sulfur atoms in one molecule is included in the photopolymerizable compound (A3).

[0049] (Photopolymerization initiator) As described above, the composition (X) contains a photopolymerization initiator (B). The photopolymerization initiator (B) is not particularly limited as long as it is a compound that decomposes when irradiated with light and generates radical species. The photopolymerization initiator (B) includes at least one compound selected from the group consisting of, for example, aromatic ketones, acylphosphine oxide compounds, aromatic onium salt compounds, organic peroxide compounds, thio compounds (thioxanthone compounds, thiophenyl group-containing compounds, etc.), hexaarylbiimidazole compounds, ketoxime ester compounds, borate compounds, azinium compounds, metallocene compounds, active ester compounds, compounds having a carbon-halogen bond, and alkylamine compounds.

[0050] The content of the photopolymerization initiator (B) is preferably 0.5% by mass or more relative to the photopolymerizable compound (A), and this content is preferably 5% by mass or less relative to the photopolymerizable compound (A).

[0051] The photopolymerization initiator (B) may contain a sensitizer, which can promote the radical generation reaction of the photopolymerization initiator (B) to improve the reactivity of the radical polymerization and the crosslink density. The sensitizer includes, for example, at least one compound selected from the group consisting of 9,10-dibutoxyanthracene, 9-hydroxymethylanthracene, thioxanthone, 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2-chlorothioxanthone, 2,4-diethylthioxanthone, anthraquinone, 1,2-dihydroxyanthraquinone, 2-ethylanthraquinone, 1,4-diethoxynaphthalene, p-dimethylaminoacetophenone, p-diethylaminoacetophenone, p-dimethylaminobenzophenone, p-diethylaminobenzophenone, 4,4′-bis(dimethylamino)benzophenone, 4,4′-bis(diethylamino)benzophenone, p-dimethylaminobenzaldehyde, and p-diethylaminobenzaldehyde.

[0052] The content of the sensitizer is, for example, 0.1% by mass or more and 5% by mass or less relative to the solid content of the composition (X). Within this range, the composition (X) can be cured in air, eliminating the need to cure the composition (X) in an inert atmosphere such as a nitrogen atmosphere. Here, the solid content of the composition (X) refers to the components in the composition (X) excluding the solvent. Note that the composition (X) does not need to contain a solvent. The composition (X) may contain a solvent, but the content of the solvent relative to the composition (X) is preferably 1% by mass or less.

[0053] (Inorganic Filler) The composition (X) may contain an inorganic filler (C). In this case, the refractive index of the cured product can be easily increased. However, since the photopolymerizable compound (A) contains the sulfur-containing monomer (A1), the refractive index of the cured product is increased. Therefore, in order to increase the refractive index of the cured product, the composition (X) does not need to contain the inorganic filler (C), or even if the inorganic filler (C) is contained, its content can be reduced. This makes it easier to suppress the wettability of the composition (X) when applied to an inorganic material. Note that when the composition (X) contains the inorganic filler (C), the content of the inorganic filler (C) is preferably 30% by mass or less relative to the composition (X). This content is more preferably 25% by mass or less, and even more preferably 20% by mass or less.

[0054] Furthermore, when the composition (X) contains an inorganic filler (C), the inorganic filler (C) is preferably nanosized. In this case, the cured product can have a high refractive index while maintaining good transparency (visible light transmittance). Nanosized means that the average particle size is 1 nm or more and 1000 nm or less. The average particle size of the inorganic filler (C) is preferably 30 nm or less, more preferably 20 nm or less. Furthermore, this average particle size is preferably 5 nm or more, more preferably 10 nm or more. Note that this average particle size is the median diameter calculated from the measurement results using dynamic light scattering, i.e., the cumulative 50% diameter (D50). Note that the Nanotrac Wave series manufactured by Microtrackbell Co., Ltd. can be used as a measuring device.

[0055] (Additives) The composition (X) may contain other components (hereinafter also referred to as additives (D)) in addition to the photopolymerizable compound (A), photopolymerization initiator (B), and inorganic filler (C) described above.

[0056] The additive (D) may contain at least one selected from the group consisting of a polymerization accelerator, a surface conditioner, a leveling agent, an ultraviolet absorber, an antioxidant, and a polymerization inhibitor. The polymerization accelerator may, for example, contain at least one amine compound selected from the group consisting of ethyl p-dimethylaminobenzoate, 2-ethylhexyl p-dimethylaminobenzoate, methyl p-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, and butoxyethyl p-dimethylaminobenzoate. From the viewpoint of suppressing the wettability of the composition (X) when applied to an inorganic material, it is preferable that the additive (D) contains almost no at least one selected from the group consisting of a surface conditioner and a leveling agent.

[0057] 2.2 Physical Properties (Refractive Index) The refractive index of the cured product can be suitably high. The refractive index of the cured product at 25°C is preferably 1.60 or higher. In this case, the light extraction efficiency of the cured product can be improved. This refractive index is more preferably 1.63 or higher, and even more preferably 1.65 or higher. There is no particular upper limit to this refractive index, but it is, for example, 1.90 or lower. Such a refractive index of the cured product can be achieved by appropriately adjusting the composition of composition (X) within the range described above. The method and conditions for measuring the refractive index of the cured product will be explained in the Examples section below.

[0058] (Viscosity) The composition (X) has a moderately low viscosity. Therefore, the composition (X) has good moldability. Therefore, the composition (X) can be molded by discharging it by an inkjet method. That is, when producing a cured product or an optical component (microlens 10) from the composition (X), the composition (X) can be molded by discharging it by an inkjet method. In other words, the composition (X) is used for applications in which molding is performed by discharging it by an inkjet method. Note that, if the composition (X) is discharged and molded by an inkjet method, the cured product or the optical component (microlens 10) can be produced with good positional accuracy.

[0059] It is also preferable that the viscosity of composition (X) at 25°C is 40 mPa s or less. It is more preferable that the viscosity of composition (X) at 25°C is 30 mPa s or less, and even more preferable that it is 28 mPa s or less. It is also preferable that this viscosity is 1 mPa s or more, more preferably 5 mPa s or more, even more preferably 10 mPa s or more, and particularly preferably 20 mPa s or more. In these cases, composition (X) can be easily molded at room temperature, and can be easily molded, particularly by an inkjet method.

[0060] Furthermore, it is preferable that the viscosity of composition (X) at 40°C is 16 mPa·s or less. In this case, regardless of the viscosity of composition (X) at room temperature, it is possible to reduce the viscosity by slightly heating composition (X). Therefore, composition (X) can be easily molded by heating, and can be easily molded by ejecting it by an inkjet method in particular. Furthermore, since the viscosity of composition (X) can be reduced without significantly heating it, changes in the composition of composition (X) due to volatilization of components in composition (X) can be made less likely. It is also preferable that this viscosity is 1 mPa·s or more, and more preferably 5 mPa·s or more.

[0061] Such a low viscosity of composition (X) can be achieved by appropriately adjusting the composition of photopolymerizable compound (A) within the range described above. The method and conditions for measuring the viscosity of composition (X) will be described in the Examples section below.

[0062] (Surface tension) The surface tension of composition (X) is preferably 30 mN / m or more and 45 mN / m or less. In this case, the ink jet properties of composition (X) can be improved, and wettability to inorganic materials can be appropriately suppressed. As a result, the shape of the cured product or optical component (microlens 10) can be formed into a semi-lens shape. This surface tension is more preferably 32 mN / m or more, and even more preferably 35 mN / m or more. Furthermore, this surface tension is more preferably, for example, 43 mN / m or less, and even more preferably 41 mN / m or less. The method and conditions for measuring surface tension will be explained in the Examples section below.

[0063] (Glass transition temperature) The glass transition temperature of the cured product of composition (X) is preferably 75°C or higher. In this case, the cured product can have good heat resistance. As a result, even if heat is applied to the cured product or the optical component (microlens 10), its shape is less likely to deform. By appropriately setting the composition of composition (X), the glass transition temperature of the cured product can be set to 85°C or higher, and can also be set to 100°C or higher. The glass transition temperature of the cured product is, for example, 150°C or lower. A method for measuring the glass transition temperature of the cured product will be explained in the Examples section.

[0064] (Contact Angle) The contact angle of composition (X) with silicon nitride is preferably 30° or more and 100° or less. In this case, when composition (X) is applied onto an inorganic material containing silicon nitride or the like, composition (X) can easily maintain a convex curved surface. As a result, the shape of the cured product or optical component (microlens 10) can be formed into a convex lens shape. This contact angle is more preferably 40° or more, and even more preferably 50° or more. Furthermore, this contact angle is more preferably, for example, 95°, and even more preferably 90° or less. The method and conditions for measuring the contact angle will be explained in the Examples section below.

[0065] 3. Uses (Optical Components) The composition (X) is suitable for use in producing optical components. In other words, the optical component includes a cured product of the composition (X). The cured product can have a moderately high refractive index. Therefore, the optical component can have high light extraction efficiency. As described above, the optical component according to the embodiment is a microlens 10. The microlens 10 is a component disposed on the path of light in an optical system. The microlens 10 preferably has a convex lens shape. In this case, the microlens 10 can have particularly high light extraction efficiency. More specifically, when light traveling in all directions passes through the microlens 10, the microlens 10 can condense the passing light by refracting it in one direction. This allows light emitted from the microlens 10 to be extracted in one direction with particular efficiency.

[0066] A method for producing an optical component using composition (X) will be described. For example, an optical component can be produced by discharging composition (X) by an inkjet method and then irradiating light onto the composition (X) to cure it. In an embodiment, a microlens 10 can be produced by discharging composition (X) by an inkjet method, forming it into droplets, and then irradiating light onto the composition (X) to cure it. In an embodiment, when discharging composition (X) by an inkjet method, if composition (X) has a sufficiently low viscosity at room temperature, for example, if the viscosity at 25°C is 40 mPa·s or less, particularly 28 mPa·s or less, composition (X) can be molded by discharging it by an inkjet method without heating. If the viscosity of composition (X) decreases when heated, composition (X) may be heated and then discharged by an inkjet method to be molded. As described above, when the viscosity of composition (X) at 40°C is particularly 16 mPa s or less, the viscosity of composition (X) can be reduced by simply heating it slightly, and in this case, the reduced-viscosity composition (X) can be ejected by an inkjet method. The heating temperature of composition (X) is, for example, 20°C or higher and 50°C or lower.

[0067] According to such a method, an optical part can be produced. Note that the method for molding composition (X) is not limited to only the ink-jet method, and composition (X) can be molded by various methods and then cured to produce a cured product or an optical part, depending on the mode of use.

[0068] (Light-emitting device) A light-emitting device can be manufactured from the composition (X). In other words, the light-emitting device includes an optical component manufactured from the composition (X). In this case, the light-emitting device can have high light extraction efficiency. The light-emitting device 1 according to the embodiment includes a microlens 10 (see FIG. 1 ). More specifically, the light-emitting device 1 according to the embodiment includes a support substrate 2, a light-emitting element 4 arranged on the support substrate 2, a sealing layer 5 arranged on the light-emitting element 4, and a microlens 10 arranged on the sealing layer 5, and the microlens 10 includes a cured product of the composition (X).

[0069] An example of the structure of the light emitting device 1 according to the embodiment will be described in more detail. The light emitting device 1 includes a support substrate 2, a light emitting element 4 disposed on the support substrate 2, a sealing layer 5 disposed on the light emitting element 4, and a microlens 10 disposed on the sealing layer 5.

[0070] In this embodiment, the light emitting device 1 includes a transparent substrate 3 facing the support substrate 2 with a gap therebetween. The light emitting device 1 also includes a passivation layer 6 covering the light emitting element 4.

[0071] The support substrate 2 is made of, for example, a resin material, but is not limited to this.

[0072] The transparent substrate 3 is made of a light-transmitting material, such as a glass substrate or a transparent resin substrate.

[0073] The light-emitting element 4 includes, for example, a pair of electrodes 41 and 43 and an organic light-emitting layer 42 between the electrodes 41 and 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, which are stacked in the above order.

[0074] Furthermore, 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.

[0075] 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 element array 9) on a support substrate 2. The element array 9 also includes a partition wall 7. The partition wall 7 is located on the support substrate 2 and separates two adjacent light-emitting elements 4. The partition wall 7 is fabricated, for example, by molding 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 to each other. The connection wiring 8 is provided on the partition wall 7.

[0076] The passivation layer 6 corresponds to an inorganic material. The passivation layer 6 is preferably made of silicon nitride or silicon oxide, and particularly preferably made of silicon nitride. In the example shown in FIG. 1 , the passivation layer 6 includes a first passivation layer 61 and a second passivation layer 62. The first passivation layer 61 is in direct contact with the element array 9 and covers the element array 9, thereby covering the light-emitting element 4. The second passivation layer 62 is disposed on the opposite side of the first passivation layer 61 from the element array 9, and a gap is provided between the second passivation layer 62 and the first passivation layer 61. The sealing layer 5 is filled between the first passivation layer 61 and the second passivation layer 62. In other words, the first passivation layer 61 is interposed between the light-emitting element 4 and the sealing layer 5 covering the light-emitting element 4.

[0077] The microlenses 10 are disposed on the second passivation layer 62. A plurality of microlenses 10 are arranged side by side, and two adjacent microlenses 10 may be connected to each other, but it is preferable that they are not connected to each other in order to ensure the flatness of the microlenses 10.

[0078] Furthermore, the microlens 10 and the light-emitting element 4 face each other in the direction D2. Therefore, even if the light emitted from the light-emitting element 4 is diffused, the microlens 10 can easily focus the light by refracting the light emitted from the light-emitting element 4 that passes through the microlens 10 in a direction along the second direction D2. This allows the microlens 10 to extract light particularly efficiently in the direction along the second direction D2.

[0079] The microlens 10 has a convex lens shape. The dimensions of the microlens 10 are not particularly limited, but can be determined, for example, according to the dimensions of the light-emitting element 4 included in the light-emitting device 1 equipped with the microlens 10. The length of the microlens 10 along the second direction D2 is preferably equal to or less than half the length along the first direction D1, and specifically, the length of the microlens 10 along the first direction D1 is, for example, 30 μm or more and 50 μm or less.

[0080] The microlens 10 is covered with a second sealing layer 52. The second sealing layer 52 is made of, for example, a photocurable and transparent resin material. As described above, the microlens 10 can have a moderately high refractive index. Therefore, the difference in refractive index between the microlens 10 and the second sealing layer 52 can be large, which makes it easier to focus light emitted from the light-emitting element 4 that passes through the microlens 10 by refracting it in a direction along the second direction D2. Specifically, the difference in refractive index between the microlens 10 and the second sealing layer 52 is preferably 0.1 or more and 0.4 or less, and more preferably 0.2 or more and 0.4 or less. The material of the second sealing layer 52 is not particularly limited as long as it satisfies the above refractive index relationship. The material of the second sealing layer 52 may be the same as or different from the sealing layer 5.

[0081] The transparent substrate 3 is disposed on the second sealing layer 52 .

[0082] A method for manufacturing a light-emitting device using composition (X) will be described. The light-emitting device includes an optical component manufactured from composition (X). Therefore, the method may include manufacturing the optical component by discharging composition (X) by an inkjet method and then irradiating light onto composition (X) to cure it. In other words, the method for manufacturing the light-emitting device 1 according to the embodiment may include manufacturing a microlens 10 by discharging composition (X) by an inkjet method and then irradiating light onto composition (X) to cure it.

[0083] The method for manufacturing the light emitting device 1 according to the embodiment will be described in more detail.

[0084] First, a support substrate 2 is prepared. On one surface of this 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. It is particularly 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.

[0085] Next, a first passivation layer 61 is provided on the element array 9. The first passivation layer 61 can be formed by a vapor deposition method such as plasma CVD.

[0086] Next, the sealing layer 5 is formed on the first passivation layer 61 .

[0087] Next, a second passivation layer 62 is provided on the sealing layer 5. The second passivation layer 62 can be formed by a vapor deposition method such as a plasma CVD method.

[0088] Next, a microlens 10 is provided on the second passivation layer 62. The composition (X) is ejected onto the second passivation layer 62 by, for example, an inkjet method and molded to form a coating film. Subsequently, the coating film of the composition (X) is cured by irradiating it with light to produce the microlens 10. When irradiating the composition (X) with light, the composition (X) may be irradiated with light in an atmosphere containing oxygen, such as the air atmosphere, or may be irradiated with light in an inert atmosphere, such as a nitrogen atmosphere.

[0089] Next, the second sealing layer 52 is formed so as to cover the microlenses 10. The second sealing layer 52 is formed by providing a photocurable resin material on the microlenses 10. Then, the transparent substrate 3 is placed on the second sealing layer 52.

[0090] A light-emitting device can be manufactured according to such a method. Note that the method for manufacturing a light-emitting device does not necessarily include manufacturing an optical component by discharging composition (X) by an ink-jet method and then irradiating composition (X) with light to cure it, and for example, the light-emitting device may include an optical component manufactured by molding using a method other than the ink-jet method.

[0091] Furthermore, the structure of the light emitting device is not limited to that shown in FIG. 1, and composition (X) can be used to manufacture light emitting devices having various structures.

[0092] 4. Aspects The composition (X) according to the first aspect of the present disclosure contains a photopolymerizable compound (A) and a photopolymerization initiator (B). The photopolymerizable compound (A) contains a sulfur-containing monomer (A1) containing 10% by mass or more of sulfur atoms per molecule. The composition (X) is liquid.

[0093] According to this embodiment, the composition (X) has a high refractive index when cured, and can suppress wettability when applied to an inorganic material.

[0094] In the composition (X) according to the second aspect of the present disclosure, in the first aspect, the sulfur-containing monomer (A1) includes a sulfur-containing monomer (A111) containing 20 mass% or more of aromatic rings per molecule.

[0095] In the composition (X) according to the third aspect of the present disclosure, in the first or second aspect, the content of the sulfur-containing monomer (A1) is 15 mass% or more relative to the photopolymerizable compound (A).

[0096] In the composition (X) according to the fourth aspect of the present disclosure, in any one of the first to third aspects, the sulfur-containing monomer (A1) includes at least one selected from the group consisting of bis(4-methacryloylthiophenyl)sulfide, 2-(2-pyridinyldithio)ethyl methacrylate, phenylthioethyl acrylate, bis(4-vinylthiophenyl)sulfide, and naphthalenylthioethyl acrylate.

[0097] In the composition (X) according to the fifth aspect of the present disclosure, in any one of the first to fourth aspects, the photopolymerizable compound (A) further includes a radically polymerizable compound (A2) other than the sulfur-containing monomer (A1). The radically polymerizable compound (A2) includes at least one selected from the group consisting of an aromatic ring-containing (meth)acrylic compound (A21) and a polyfunctional (meth)acrylic compound (A22).

[0098] The composition (X) according to the sixth aspect of the present disclosure, in any one of the first to fifth aspects, does not contain an inorganic filler (C) or further contains an inorganic filler (C), and the content of the inorganic filler (C) is 30 mass% or less relative to the composition (X).

[0099] Composition (X) according to the seventh aspect of the present disclosure, in any one of the first to sixth aspects, has a surface tension at 25°C of 30 mN / m or more and 45 mN / m or less.

[0100] Composition (X) according to an eighth aspect of the present disclosure, in any one of the first to seventh aspects, has a viscosity at 25°C of 40 mPa·s or less.

[0101] In the composition (X) according to the ninth aspect of the present disclosure, in any one of the first to eighth aspects, the refractive index of the cured product at 25°C is 1.60 or more.

[0102] The composition (X) according to the tenth aspect of the present disclosure, in any one of the first to ninth aspects, is used for an application in which molding is carried out by ejecting the composition by an inkjet method.

[0103] The composition (X) according to the eleventh aspect of the present disclosure is for producing a microlens in the first to tenth aspects.

[0104] A method for producing an optical component according to a twelfth aspect of the present disclosure includes discharging composition (X) according to any one of the first to eleventh aspects by an inkjet method, and then irradiating composition (X) with light to cure it, thereby producing an optical component.

[0105] A method for manufacturing an optical component according to a thirteenth aspect of the present disclosure is the twelfth aspect, wherein the optical component is a microlens.

[0106] A light-emitting device (1) according to a fourteenth aspect of the present disclosure includes a support substrate (2), a light-emitting element (4) disposed on the support substrate (2), a sealing layer (5) disposed on the light-emitting element (4), and a microlens (10) disposed on the sealing layer (5). The microlens (10) includes a cured product of the composition (X) according to any one of the first to eleventh aspects.

[0107] Specific examples of the embodiments will be described below, but the present disclosure is not limited to these examples.

[0108] 1. Preparation of Compositions 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: - Sulfur-containing monomer #1: bis(4-methacryloylthiophenyl) sulfide. Manufactured by Tokyo Chemical Industry Co., Ltd. Sulfur atom content: 25% by mass. Aromatic ring content: 37% by mass. Refractive index (cured film): 1.71. - Sulfur-containing monomer #2: 2-(2-pyridinyldithio)ethyl methacrylate. Manufactured by Tokyo Chemical Industry Co., Ltd. Product name: VMOX. Sulfur atom content: 26% by mass. Aromatic ring content: 30% by mass. Refractive index (cured film): 1.63. - Sulfur-containing monomer #3: phenylthioethyl acrylate. Manufactured by BIMAX Corporation. Product name: PTEA. Sulfur atom content: 15% by mass. Aromatic ring content: 35% by mass. Refractive index (cured film): 1.61. - Sulfur-containing monomer #4: Bis(4-vinylthiophenyl) sulfide. Manufactured by Sumitomo Seika Chemicals Co., Ltd. Product name: MPV. Sulfur atom content: 32% by weight. Aromatic ring content: 48% by weight. Refractive index (cured film): 1.73. - Sulfur-containing monomer #5: Naphthalenylthioethyl acrylate. Manufactured by Daelim Chemical Electromer company. Product name: HRI-02. Sulfur atom content: 11% by weight. Aromatic ring content: 43% by weight. Refractive index (cured film): 1.66. - Sulfur-containing monomer #6: 8-(allylthio)-1,3-dimethyl-7-(3-methylbenzyl)-3,7-dihydro-1H-purine-2,6-dione. Manufactured by Sigma-Aldrich. Product name: R145866. Sulfur atom content: 9% by weight. Aromatic ring content: 20% by weight. Refractive index (cured film): 1.65. - Aromatic ring-containing (meth)acrylic compound #1: naphthyl methyl acrylate. Manufactured by Kyoeisha Chemical Co., Ltd. Product name: NMT-A. Aromatic ring content: 57% by weight. Refractive index (cured film): 1.64. - Aromatic ring-containing (meth)acrylic compound #2: ethoxylated o-phenylphenol acrylate. Manufactured by Shin-Nakamura Chemical Co., Ltd. Product name: A-LEN-10. Aromatic ring content: 54% by weight. Refractive index (cured film): 1.61. - Multifunctional (meth)acrylic compound #1: 1,10-decanediol diacrylate. Manufactured by Shin-Nakamura Chemical Co., Ltd. Product name: A-DOD-N. Refractive index (cured film): 1.52. - Multifunctional (meth)acrylic compound #2: pentaerythritol triacrylate. Manufactured by Kyoeisha Chemical Co., Ltd. Product name: PE-3A. Refractive index (cured film): 1.52.- Photopolymerization initiator #1: acylphosphine oxide-based photopolymerization initiator. Manufactured by IGM Resins B.V. Product name: Omnirad TPO H. - Inorganic filler #1: zirconium oxide. Manufactured by Sakai Chemical Industry Co., Ltd. Product name: SZR-CW. Refractive index (cured film): 2.1. Average particle size: 6 nm. Specific gravity: 5.6.

[0109] 2. Evaluation The compositions were subjected to the following evaluation tests, the results of which are shown in the table below.

[0110] (1) Refractive Index A composition was applied to form a coating film having a thickness of 300 μm, and the coating film was irradiated with light having a peak wavelength of 395 nm at an irradiation intensity of 0.5 W / cm using a UV irradiator (manufactured by Ushio Inc., Model No. Unijet E075IIHD) under a nitrogen atmosphere. ２ And the cumulative light intensity is 1.5 J / cm ２ The refractive index of this sample at a wavelength of 589 nm in an atmosphere at 25°C was measured using a multi-wavelength Abbe refractometer (manufactured by Atago, model number DR-M2).

[0111] (2) Viscosity at 25°C The viscosity of the composition was measured using a rheometer (manufactured by Anton Paar Japan, model number DHR-2) at a temperature of 25°C and a shear rate of 1000 s －１ The measurement was carried out under the following conditions.

[0112] (3) Viscosity at 40°C The viscosity of the composition was measured using a rheometer (manufactured by Anton Paar Japan, model number DHR-2) at a temperature of 40°C and a shear rate of 1000 s －１ The measurement was carried out under the following conditions.

[0113] (4) Surface Tension The surface tension of the composition was measured using a contact angle meter (manufactured by Kyowa Interface Science Co., Ltd., Model PCA-1) with a droplet volume of 4 μL.

[0114] (5) Glass Transition Temperature A coating film was prepared by applying a composition, and the coating film was irradiated with light having a peak wavelength of 395 nm at an irradiation intensity of 3 W / cm using a UV irradiator (manufactured by Ushio Inc., Model No. Unijet E075IIHD) in an air atmosphere. ２ And the cumulative light intensity is 1.5 J / cm ２The coating was photocured by irradiating under the conditions of

[0043]

[0044]

[0045]

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[0050]

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[0052]

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[0054]

[0055]

[0056]

[0057]

[0058]

[0059]

[0060]

[0061]

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

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[0082]

[0115] (6) Evaluation of Substrate Contact Angle A silicon nitride film was formed on a glass slide by plasma CVD. Subsequently, a contact angle meter (manufactured by Kyowa Interface Science Co., Ltd., Model PCA-1) was used to measure the contact angle of a 2 μL droplet of the composition with the silicon nitride film 7 seconds after it was applied.

[0116] A contact angle of 30° or more was evaluated as "A," a contact angle of 20° or more but less than 30° was evaluated as "B," and a contact angle of less than 20° was evaluated as "C."

[0117] (7) Inkjet Properties The composition was placed in a cartridge of an inkjet printer (manufactured by Fujifilm Corporation, product name: Material Printer MP2831), and droplets of the composition were ejected from the nozzle of the inkjet printer under conditions of a temperature of 40°C and a frequency of 1 kHz. The droplets were observed with a high-speed camera. The results were evaluated as follows: "A" if the droplets did not separate; "B" if the satellites separated from the original droplets and then merged with the original droplets to form a single droplet again; "C" if the satellites separated from the original droplets and did not merge; and "D" if ejection was not possible.

[0118] (8) Curability The composition was measured using an infrared spectrometer (Agilent Technologies, Model No. Agilent Cary 610 FTIR Microscope System) to obtain an IR spectrum.

[0119] The composition was applied to form a coating film having a thickness of 10 μm, and the coating film was irradiated with light having a peak wavelength of 395 nm at an irradiation intensity of 0.5 W / cm using a UV irradiator (manufactured by Ushio Inc., model number Unijet E075IIHD) under a nitrogen atmosphere. ２ And the cumulative light intensity is 1.5 J / cm ２ Subsequently, the composition (cured product) after irradiation with ultraviolet light was measured using the above-mentioned infrared spectrometer to obtain an IR spectrum.

[0120] In each of the two IR spectra, －１ The peak intensity of the absorption of the acryloyl group appearing in the coating film was measured. ０ and the peak intensity I for the cured product １ From this, {1-(I ０ -I １ ) / I ０ The reduction rate of the reactive functional groups in the composition before and after irradiation with ultraviolet light was calculated using the formula: × 100 (%). The result was taken as the reaction rate, and the reaction rate was evaluated as "A" when it was 90% or more, "B" when it was 80% or more but less than 90%, and "C" when it was less than 80%.

[0121] (9) Brightness Evaluation A glass substrate with an ITO electrode was prepared. The planar dimensions of the glass substrate with an ITO electrode were 30 mm x 30 mm, the thickness of the ITO electrode was 150 nm, and the total thickness of the glass substrate with an ITO electrode was 700 μm.

[0122] The glass substrate with the ITO electrode was washed with acetone and then with isopropanol.

[0123] Next, a hole injection layer, a hole transport layer, a light-emitting layer, an electron injection layer, and a cathode were sequentially formed on the anode by vacuum deposition using the 150 nm-thick ITO electrode on the glass substrate with the ITO electrode, thereby producing an organic EL device having a structure of anode / hole injection layer / hole transport layer / light-emitting layer / electron injection layer / cathode and measuring 2 mm × 2 mm in plan view.

[0124] The hole injection layer was made from 4,4′,4″-tris{2-naphthyl(phenyl)amino}triphenylamine (2-TNATA).

[0125] The hole transport layer was made from N,N'-diphenyl-N,N'-dinaphthylbenzidine (α-NPD).

[0126] The light-emitting layer was made of tris(8-hydroxyquinolinato)aluminum, a metal complex material. The thickness of the light-emitting layer was 100 nm. This light-emitting layer also functions as an electron transport layer.

[0127] The electron injection layer was made from lithium fluoride.

[0128] The cathode was made of aluminum and had a thickness of 150 nm.

[0129] In this way, an organic EL element was fabricated on the glass substrate.

[0130] Next, a mask (cover) having an opening of 10 mm × 10 mm in plan view was placed on the glass substrate so that the organic EL element was exposed through the opening. In this state, a SiN film (first passivation layer) having a size of 10 mm × 10 mm in plan view was formed by plasma CVD so as to cover the organic EL element.

[0131] Subsequently, the composition was ejected onto the first passivation layer using an inkjet printer (manufactured by Fujifilm Corporation, product name: Material Printer MP2831) under a nitrogen atmosphere to form droplets at a temperature of 40° C. and a voltage of 15 V.

[0132] Then, the droplets were irradiated with light having a peak wavelength of 395 nm using a UV irradiator (manufactured by Ushio Inc., model number Unijet E075IIHD) at an irradiation intensity of 3 W / cm. ２ And the cumulative light intensity is 1.5 J / cm ２ The coating was cured to form a microlens.

[0133] Subsequently, the substrate was attached to a non-alkali glass plate (manufactured by Corning, product name Eagle XG) measuring 30 mm x 30 mm x 0.7 mm using an epoxy resin adhesive, thereby completing the production of an organic EL light-emitting device.

[0134] The luminance value was obtained from 0° using EZcontrast (Eldim) with the front of the panel as 0°. The luminance value of Comparative Example 1 was defined as C, and the luminance value obtained in the Examples or Comparative Examples was defined as D, and the relative luminance was calculated according to the following formula.

[0135] Relative luminance = D / C x 100 (%) Relative luminance values ​​of 110% or more were evaluated as "A", values ​​greater than 100% and less than 110% as "B", and values ​​of 100% or less as "C".

[0136]

Claims

1. A liquid photocurable resin composition comprising a photopolymerizable compound (A) and a photopolymerization initiator (B), wherein the photopolymerizable compound (A) comprises a sulfur-containing monomer (A1) containing 10% by mass or more of sulfur atoms per molecule.

2. The photocurable resin composition according to claim 1, wherein the sulfur-containing monomer (A1) comprises a sulfur-containing monomer (A111) containing 20% ​​by mass or more of aromatic rings per molecule.

3. The photocurable resin composition according to claim 1, wherein the content of the sulfur-containing monomer (A1) is 15 mass % or more relative to the photopolymerizable compound (A).

4. The photocurable resin composition according to claim 1, wherein the sulfur-containing monomer (A1) comprises at least one selected from the group consisting of bis(4-methacryloylthiophenyl)sulfide, 2-(2-pyridinyldithio)ethyl methacrylate, phenylthioethyl acrylate, bis(4-vinylthiophenyl)sulfide, and naphthalenylthioethyl acrylate.

5. The photocurable resin composition according to claim 1, wherein the photopolymerizable compound (A) further comprises a radically polymerizable compound (A2) other than the sulfur-containing monomer (A1), and the radically polymerizable compound (A2) comprises at least one compound selected from the group consisting of an aromatic ring-containing (meth)acrylic compound (A21) and a polyfunctional (meth)acrylic compound (A22).

6. The photocurable resin composition according to claim 1, which does not contain an inorganic filler (C), or which further contains an inorganic filler (C), and the content of the inorganic filler (C) is 30 mass% or less relative to the photocurable resin composition.

7. The photocurable resin composition according to claim 1, which has a surface tension at 25°C of 30 mN / m or more and 45 mN / m or less.

8. The photocurable resin composition according to claim 1, having a viscosity of 40 mPa·s or less at 25°C.

9. The photocurable resin composition according to claim 1, wherein the refractive index of the cured product at 25°C is 1.60 or more.

10. The photocurable resin composition according to claim 1, which is used for molding by being ejected by an inkjet method.

11. The photocurable resin composition according to claim 1, which is used for producing a microlens.

12. A method for manufacturing an optical component, comprising: ejecting the photocurable resin composition according to any one of claims 1 to 11 by an inkjet method; and then irradiating the photocurable resin composition with light to cure it, thereby manufacturing an optical component.

13. The method for manufacturing an optical component according to claim 12, wherein the optical component is a microlens.

14. A light-emitting device comprising: a support substrate; a light-emitting element disposed on the support substrate; a sealing layer disposed on the light-emitting element; and a microlens disposed on the sealing layer, wherein the microlens comprises a cured product of the photocurable resin composition according to any one of claims 1 to 11.

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