Photocurable composition, cured product of photocurable composition, and light-emitting device

Abstract

The present disclosure relates to a photocurable composition containing an aromatic monomer and a photopolymerization initiator, where the aromatic monomer has a first group that contains a naphthalene skeleton, an anthracene skeleton, or a biphenyl skeleton and a second group that contains at least one selected from the group consisting of (meth)acryloyl groups and vinyl (thio)ether groups; the first group bonds with the second group directly or via an oxygen atom, an alkylene group, or a (poly)oxyalkylene group; and the refractive index of a cured film at a wavelength of 486 nm is 1.55 or higher.

Description

[Technical Field]

[0001] This disclosure relates to a photocurable composition, a cured product of a photocurable composition, and a light-emitting device. [Background technology]

[0002] Regarding materials for constituting next-generation displays such as organic electroluminescent (hereinafter also referred to as "organic EL") displays, various technical means have been proposed from the viewpoint of improving optical properties. For example, Patent Document 1 discloses a curable ink composition comprising at least one aromatic (meth)acrylate, at least one polyfunctional (meth)acrylate having a heteroaromatic group, a condensed aromatic group, a heteroalkylene group, or a group containing both a heteroalkylene group and an aromatic group, and a photoinitiator, wherein the ink composition is inkjet printable, has a viscosity of 30 centipoise or less at a temperature of room temperature to 35°C, does not contain solvents, and when printed and cured, has a refractive index of 1.55 or more and is optically transparent. Patent Document 2 discloses an ultraviolet curable resin composition containing a photopolymerizable component (A) and a photopolymerization initiator (B), having a refractive index of 1.53 or more and a viscosity of 30 mP·s or less at at least one of 25°C or 40°C. [Prior art documents] [Patent Documents]

[0003] [Patent Document 1] Special Publication No. 2020-506251 [Patent Document 2] Japanese Patent Publication No. 2021-55051 [Overview of the project] [Problems that the invention aims to solve]

[0004] In light-emitting devices such as organic EL displays, increasing brightness is a challenge. The main cause of brightness reduction is the decrease in light extraction efficiency due to the phenomenon of total internal reflection of light from the light-emitting layer at interfaces with a difference in refractive index. In particular, the difference in refractive index between the inorganic layer, which consists of silicon nitride film (refractive index 1.9) or indium tin oxide (refractive index 2.1), and the resin layer, which consists of a polarizing plate or optical adhesive (refractive index less than 1.55), has a significant effect on brightness reduction. Therefore, in order to improve the light extraction rate at the interface between the inorganic layer and the resin layer, a light extraction layer having a high refractive index (e.g., a refractive index of 1.55 or higher) is sometimes provided between the inorganic layer and the resin layer. For the formation of the light extraction layer, a photocurable composition that can be applied by an inkjet device and can form a cured film with a high refractive index (e.g., 1.55 or higher) while having high transmittance is useful.

[0005] The main object of this disclosure is to provide a photocurable composition that can be applied by an inkjet device and that can form a cured film having a high refractive index at a wavelength of 486 nm while also having high transmittance. [Means for solving the problem]

[0006] One aspect of this disclosure relates to the following [1] to

[18] . [1] A photocurable composition comprising an aromatic monomer and a photopolymerization initiator, wherein the aromatic monomer comprises a first group comprising a naphthalene skeleton, anthracene skeleton, or biphenyl skeleton, and a second group comprising at least one selected from the group consisting of a (meth)acryloyl group and a vinyl (thio) ether group, wherein the first group is bonded to the second group via an oxygen atom, an alkylene group, or a (poly)oxyalkylene group, or directly, and the refractive index of the cured film at a wavelength of 486 nm is 1.55 or higher. [2] The photocurable composition according to [1], wherein the content of the aromatic monomer is 50% by mass or more based on the total amount of the photocurable composition. [3] The photocurable composition according to [1] or [2], further comprising a diaryl sulfide compound. [4] The photocurable composition according to [3], wherein the diaryl sulfide compound has at least one selected from the group consisting of a hydroxyl group, a mercapto group, a (meth)acryloyl group, and a vinyl (thio)ether group. [5] The photocurable composition according to [3] or [4], wherein the content of the diaryl sulfide compound is 20% by mass or more based on the total amount of the photocurable composition. [6] The photocurable composition according to any one of [1] to [5], further comprising a nitroxyl radical compound. [7] The photocurable composition according to [6], wherein the nitroxyl radical compound has at least one selected from the group consisting of a hydroxyl group, a mercapto group, a (meth)acryloyl group, and a vinyl (thio)ether group. [8] The photocurable composition according to [6] or [7], wherein the content of the nitroxyl radical compound is 0.05% by mass or more and 0.60% by mass or less based on the total amount of the photocurable composition. [9] The photocurable composition according to any one of [1] to [8], further comprising a reactive diluent, wherein the reactive diluent has at least one polymerizable functional group selected from the group consisting of a (meth)acryloyl group and a vinyl (thio)ether group, and the viscosity of the reactive diluent at 25°C is 10 mPa·s or less.

[10] The photocurable composition according to any one of [1] to [9], wherein the content of the compound having one (meth)acryloyl group and one vinyl (thio)ether group is 50% by mass or more based on the total amount of the photocurable composition.

[11] The photocurable composition according to any one of [1] to

[10] , wherein the photopolymerization initiator is a compound having one phosphorus atom and three aryl groups.

[12] The photocurable composition according to any one of [1] to

[11] , comprising a compound having a fluoro group.

[13] The photocurable composition according to

[12] , wherein the content of the compound having a fluoro group is 0.1% by mass or more and 5% by mass or less based on the total mass of the photocurable composition.

[14] The photocurable composition according to any one of [1] to

[13] , wherein the photocurable composition is liquid at 23°C, and the number of liquid particles with a particle size of 1 μm or more contained in the photocurable composition at 23°C is 10 particles / ml or less.

[15] The photocurable composition according to any one of [1] to

[14] , wherein the viscosity at 25°C after storing the photocurable composition in a 40°C environment for 120 hours is 30 mPa·s or less.

[16] A photocurable composition that can be applied by an inkjet device, as described in any of [1] to

[15] .

[17] A cured product of any of the photocurable compositions described in [1] to

[16] .

[18] A light-emitting device comprising a cured product of a photocurable composition described in any of [1] to

[16] .

[19] The light-emitting device described in

[18] , which is an organic EL display. [Effects of the Invention]

[0007] According to this disclosure, it is possible to provide a photocurable composition that can be applied by an inkjet device and that can form a cured film having a high refractive index at a wavelength of 486 nm while also having high transmittance. [Brief explanation of the drawing]

[0008] [Figure 1] This is a schematic cross-sectional view showing one embodiment of a laminate including a light extraction layer. [Modes for carrying out the invention]

[0009] Embodiments of this disclosure will be described in detail below. However, the present invention is not limited to the embodiments described below. In numerical ranges, "greater than or equal to A" means A and the range greater than A. In numerical ranges, "less than or equal to A" means A and the range less than A. In numerical ranges described stepwise in this specification, the upper or lower limit of a numerical range in one step can be arbitrarily combined with the upper or lower limit of a numerical range in another step. In numerical ranges described in this specification, the upper or lower limit of a numerical range can be replaced with the value shown in the examples. "A or B" means that either A or B may be included, or both may be included. Unless otherwise specified, the materials exemplified in this specification may be used alone or in combination of two or more. The content of each component in a composition means the total amount of multiple substances present in the composition if there are multiple substances corresponding to each component in the composition, unless otherwise specified.

[0010] In this specification, "(meth)acryloyl group" refers to a methacryloyl group or an acryloyl group. In this specification, "vinyl (thio)ether group" refers to a vinyl ether group (-O-CH=CH2) or a vinyl thioether group (-S-CH=CH2). In this specification, "(poly)oxyalkylene group" refers to an oxyalkylene group or a polyoxyalkylene group. An oxyalkylene group means a group in which an oxy group (-O-) and an alkylene group are directly bonded. A polyoxyalkylene group means a group in which two or more alkylene groups are linked by an oxy group.

[0011] [Photocurable composition] One embodiment of the present disclosure is a photocurable composition that can be applied by an inkjet device. The photocurable composition comprises an aromatic monomer and a photopolymerization initiator.

[0012] <Aromatic monomers> The aromatic monomer has a first group comprising a naphthalene skeleton, anthracene skeleton, or biphenyl skeleton, and a second group comprising at least one selected from the group consisting of a (meth)acryloyl group and a vinyl (thio) ether group. The aromatic monomer may be a compound having one of the first groups in its molecule.

[0013] Aromatic monomers may have one or more second groups within the molecule. The number of second groups may be one or more, three or less, or two or less. The number of second groups may be one to two, or one. When the number of second groups is one, a photocurable composition with lower viscosity at 25°C is obtained, and the storage stability of the photocurable composition is further improved. When an aromatic monomer contains multiple second groups within the molecule, the multiple second groups may be of the same type or different types.

[0014] The first group is bonded to the second group via an oxygen atom (-O-), an alkylene group, or a (poly)oxyalkylene group, or directly.

[0015] The number of carbon atoms in the alkylene group may be, for example, 1 or more, and may be 6 or less, 5 or less, 4 or less, 3 or less, or 2 or less. Examples of alkylene groups include methylene group, ethylene group, n-propylene group, isopropylene group, n-butylene group, isobutylene group, sec-butylene group, tert-butylene group, n-pentylene group, isopentylene group, sec-pentylene group, tert-pentylene group, n-hexylene group, isohexylene group, sec-hexylene group, tert-hexylene group, and the like.

[0016] The (poly)oxyalkylene group may be, for example, a (poly)oxymethylene group, a (poly)oxyethylene group, a (poly)oxypropylene group, a (poly)oxybutylene group, a (poly)oxypentylene group, or a (poly)oxyhexylene group.

[0017] The aromatic monomer may be a compound represented by the following formula (1), wherein the first group comprises a naphthalene skeleton and the second group comprises a (meth)acryloyl group. [ka]

[0018] In formula (1), n1 represents an integer from 1 to 8. n1 is 1 or greater and may be 7 or less, 6 or less, 5 or less, 3 or less, or 2 or less. n1 may be 1. When n1 is 1, in addition to obtaining a photocurable composition with lower viscosity at 25°C, the storage stability of the photocurable composition is further improved.

[0019] Z 1 This represents a single bond, or an oxygen atom, an alkylene group, or a (poly)oxyalkylene group. 1 Z may be bonded to any position on the naphthalene ring. 1 This is an oxygen atom (-O-) or an oxyalkylene group (*1-Z 1a -O-*2) may be the case. Here, *1 indicates the bonding site with the naphthalene ring, and *2 indicates the bonding site with the (meth)acryloyl group. Z 1a This indicates an alkylene group. 1a The alkylene group represented by may be a methylene group (-CH2-).

[0020] R 1 represents a hydrogen atom or a methyl group. When n1 is 2 or more, the substituents bonded to the naphthalene ring may be of the same type or different types.

[0021] The aromatic monomer may be a compound represented by the following formula (2), wherein the first group contains an anthracene skeleton and the second group contains a (meth)acryloyl group. [ka]

[0022] n2 represents an integer from 1 to 10. n2 can be 1 or more, and can be 8 or less, 6 or less, 4 or less, 3 or less, or 2 or less.

[0023] Z 2 represents a single bond, an oxygen atom, an alkylene group, or a (poly)oxyalkylene group. Z 2 can be bonded to any position of the anthracene ring. For example, it can be bonded to the 1st, 2nd, or 9th position of the anthracene ring. Z 2 can be an oxygen atom (-O-) or an oxyalkylene group (*1-Z 2a -O-*2). Here, *1 indicates the bonding site with the anthracene ring, and *2 indicates the bonding site with the (meth)acryloyl group. Z 1a represents an alkylene group. Z 2a The alkylene group represented by may be a methylene group (-CH2-).

[0024] R 2 represents a hydrogen atom or a methyl group. When n2 is 2 or more, the plurality of substituents bonded to the anthracene ring may each be the same kind of group or different kinds of groups.

[0025] The aromatic monomer may be a compound represented by the following formula (3) in which the first group contains a biphenyl skeleton and the second group contains a (meth)acryloyl group.

Chemical formula

[0026] n3 and n4 each independently represent an integer from 1 to 10. n3 and n4 are 1 or more, and each independently can be 8 or less, 6 or less, 4 or less, 3 or less, or 2 or less, and can be 1.

[0027] Z 3 and Z 4 each independently represent a single bond, an oxygen atom, an alkylene group, or a (poly)oxyalkylene group. Z 3 and Z 4 can be bonded to any position of the benzene ring. Z3 and Z 4 For example, (poly)oxyalkylene group (*3-OZ 5 -O-*4) may be the case. Here, *3 indicates the bonding site with the benzene ring, and *4 indicates the bonding site with the (meth)acryloyl group. Z 5 This can be an ethylene group (-CH2-CH2-).

[0028] R 3 and R 4 Each of these independently represents either a hydrogen atom or a methyl group. When n3 and n4 are 2 or more, the substituents bonded to the benzene ring may be of the same type or different types.

[0029] An aromatic monomer in which the first group contains a biphenyl skeleton and the second group contains a (meth)acryloyl group may be a compound represented by the following formula (3a).

[0030] [ka]

[0031] In formula (3a), Z 3 and R 3 Z in equation (3) 3 and R 3 It is synonymous with [the above].

[0032] The aromatic monomer may include one or more aromatic monomers in which the first group contains a naphthalene skeleton, and may include an aromatic monomer in which the first group contains a naphthalene skeleton, an aromatic monomer in which the first group contains an anthracene skeleton, or an aromatic monomer in which the first group contains a biphenyl skeleton.

[0033] At least some of the hydrogen atoms on the aromatic rings in the naphthalene skeleton, anthracene skeleton, and biphenyl skeleton may be substituted with substituents other than the second group and the group linking the second group and the first group (other substituents). Examples of other substituents include alkyl groups, alkoxy groups, thioalkyl groups, hydroxyl groups, thiol groups, chloro groups, bromo groups, fluoro groups, amino groups, and the like.

[0034] Examples of aromatic monomers include naphthyl (meth)acrylate, naphthalene di(meth)acrylate, naphthalene methyl (meth)acrylate, naphthalene ethyl (meth)acrylate, anthracenyl (meth)acrylate, anthracenyl di(meth)acrylate, anthracene methyl (meth)acrylate, anthracene ethyl (meth)acrylate, (ortho-, meta-, or para-)phenylphenol (meth)acrylate, (ortho-, meta-, or para-)phenylphenol (meth)acrylate, methoxylated (ortho-, meta-, or para-)phenylphenol (meth)acrylate, and ethoxylated (ortho-, meta-, or para-)phenylphenol (meth)acrylate.

[0035] The aromatic monomer content may be 50% by mass or more, 60% by mass or more, 70% by mass or more, 80% by mass or more, 90% by mass or more, or 95% by mass or more, based on the total amount of the photocurable composition, and may be 99% by mass or less, 95% by mass or less, or 90% by mass or less.

[0036] The content of the aromatic monomer in which the first group contains a naphthalene skeleton may be 50 parts by mass or more, 60 parts by mass or more, 70 parts by mass or more, 80 parts by mass or more, 90 parts by mass or more, or 95 parts by mass or more, and may be 100 parts by mass or less, 99 parts by mass or less, 90 parts by mass or less, or 80 parts by mass or less, based on 100 parts by mass of the total mass of the aromatic monomer.

[0037] The content of an aromatic monomer having one second group (monofunctional aromatic monomer) may be 50 parts by mass or more, 60 parts by mass or more, 70 parts by mass or more, 80 parts by mass or more, 90 parts by mass or more, or 95 parts by mass or more, and may be 100 parts by mass or less, 99 parts by mass or less, 90 parts by mass or less, or 80 parts by mass or less, based on 100 parts by mass of the total mass of the aromatic monomer. When the content of monofunctional aromatic monomer is within the above range, a photocurable composition with lower viscosity at 25°C is obtained, and the storage stability of the photocurable composition is further improved.

[0038] <Photopolymerization initiator> As the photopolymerization initiator, a photopolymerization initiator capable of polymerizing the above-mentioned aromatic monomers can be used.

[0039] Examples of photopolymerization initiators include, Benzophenone and its derivatives; benzyl and its derivatives; Anthraquinones and their derivatives; Benzoin-type photopolymerization initiators such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin propyl ether, benzoin isobutyl ether, and benzyl dimethyl ketal; Acetophenone-type photopolymerization initiators such as diethoxyacetophenone and 4-tert-butyltrichloroacetophenone; 2-dimethylaminoethylbenzoate; p-dimethylaminoethylbenzoate; Diphenyl disulfide; Thioxanthones and their derivatives; Camphorquinone-type photopolymerization initiators such as camphorquinone, 7,7-dimethyl-2,3-dioxobicyclo[2.2.1]heptane-1-carboxylic acid, 7,7-dimethyl-2,3-dioxobicyclo[2.2.1]heptane-1-carboxy-2-bromoethyl ester, 7,7-dimethyl-2,3-dioxobicyclo[2.2.1]heptane-1-carboxy-2-methyl ester, and 7,7-dimethyl-2,3-dioxobicyclo[2.2.1]heptane-1-carboxylic acid chloride; α-aminoalkylphenone type photopolymerization initiators such as 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one and 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butanone-1; Acylphosphine oxide type photopolymerization initiators such as benzoyl diphenylphosphine oxide, 2,4,6-trimethylbenzoyl-diphenylphosphine oxide, benzoyl diethoxyphosphine oxide, 2,4,6-trimethylbenzoyl dimethoxyphenylphosphine oxide, 2,4,6-trimethylbenzoyl diethoxyphenylphosphine oxide, and bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide; Phenyl-glyoxylic acid-methyl ester; Oxyphenyl acetyl acid 2-[2-oxo-2-phenylacetoxy-ethoxy]ethyl ester; Examples include oxyphenyl acetate acid 2-[2-hydroxyethoxy]ethyl ester; and others.

[0040] The photopolymerization initiator may be a compound having one phosphorus atom and three aryl groups, or it may be an acylphosphine oxide type photopolymerization initiator having one phosphorus atom and three aryl groups. When these photopolymerization initiators are included, it is easier to obtain a cured film with superior inkjet ejection stability and higher transmittance, as well as a cured film with a higher refractive index.

[0041] The aryl group may be, for example, a substituted or unsubstituted phenyl group. The substituted phenyl group may be a group in which at least one hydrogen atom in the benzene ring is substituted with an alkyl group (for example, a methyl group). The substituted phenyl group may be a group in which 1 to 3, or 3, hydrogen atoms in the benzene ring are substituted with alkyl groups, and may be a 2,4,6-trimethylphenyl group.

[0042] Examples of acylphosphine oxide type photopolymerization initiators having one phosphorus atom and three aryl groups include 2,4,6-trimethylbenzoyl-diphenylphosphine oxide and bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide. Examples of 2,4,6-trimethylbenzoyl-diphenylphosphine oxide include "Omnirad TPO H" manufactured by IGM Resins BV. Examples of bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide include "Omnirad 819" manufactured by IGM Resins BV.

[0043] The content of the photopolymerization initiator may be 0.05% by mass or more, 0.5% by mass or more, 1% by mass or more, or 2% by mass or more, based on the total amount of the photocurable composition. The content of the photopolymerization initiator may be 10% by mass or less, 8% by mass or less, or 5% by mass or less, based on the total amount of the photocurable composition. The content of the photopolymerization initiator may be 0.05 to 10% by mass, 0.05 to 8% by mass, 0.05 to 5% by mass, 0.5 to 10% by mass, 0.5 to 8% by mass, 0.5 to 5% by mass, 1 to 10% by mass, 1 to 8% by mass, 1 to 5% by mass, 2 to 10% by mass, 2 to 8% by mass, or 2 to 5% by mass, based on the total amount of the photocurable composition.

[0044] <Other ingredients> The photocurable composition may contain components other than aromatic monomers and photopolymerization initiators (other components), or it may not contain other components. The photocurable composition may contain, for example, at least one selected from the group consisting of diaryl sulfide compounds, fluorine-containing compounds, nitroxyl radical compounds, reactive diluents, and stabilizers.

[0045] <Diaryl sulfide compounds> Diaryl sulfide compounds are compounds containing two aryl groups and a thioether bond (-S-) connecting the two aryl groups. When a photocurable composition contains a diaryl sulfide compound, a cured film with a higher refractive index is more likely to be obtained.

[0046] Diaryl sulfide compounds are of the formula:Ar 1 -S-Ar 2 It may be a compound represented by Ar. 1 and Ar 2 Each of these independently represents an aryl group. 1 and Ar 2 These groups may be of the same type or different types. Diaryl sulfide compounds may be used individually or in combination of two or more types.

[0047] The aryl group may be, for example, a substituted or unsubstituted phenyl group. The substituent in the substituted phenyl group may be, for example, a hydroxyl group or a mercapto group, or a polymerizable functional group such as a (meth)acryloyl group or a vinyl (thio) ether group.

[0048] The diaryl sulfide compound may have at least one selected from the group consisting of a hydroxyl group, a mercapto group, a (meth)acryloyl group, and a vinyl (thio) ether group.

[0049] The diaryl sulfide compound may be, for example, a compound represented by the following formula (4). [ka]

[0050] In equation (4), m1 and m2 each independently represent integers from 1 to 5. 5 and R 6 Each of these independently represents a hydroxyl group, a mercapto group, a (meth)acryloyl group, or a vinyl (thio) ether group. 5 and R 6 If there are multiple instances, then there are multiple R 5 and R 6 These groups may be of the same type or different types.

[0051] The diaryl sulfide compound may be a compound represented by the following formula (4a). [ka]

[0052] In formula (4a), R 5 and R 6 R in equation (4) 5 and R 6 It is synonymous with [the above].

[0053] The diaryl sulfide compound content may be 1% by mass or more, 5% by mass or more, 10% by mass or more, 15% by mass or more, 20% by mass or more, 25% by mass or more, 30% by mass or more, or 35% by mass or more, based on the total amount of the photocurable composition. By adjusting the diaryl sulfide compound content within the above numerical range, a photocurable composition with lower viscosity at 25°C and superior inkjet ejection stability can be obtained, and a cured film with a higher refractive index tends to be easier to obtain. The diaryl sulfide compound content may be 50% by mass or less, 45% by mass or less, 40% by mass or less, 35% by mass or less, 30% by mass or less, 25% by mass or less, 20% by mass or less, or 15% by mass or less, based on the total amount of the photocurable composition. By adjusting the diaryl sulfide compound content within the above numerical range, a cured film with higher transmittance tends to be easier to obtain.

[0054] <Fluorine-containing compounds> The photocurable compound preferably contains a compound having a fluoro group (hereinafter also referred to as "fluorine-containing compound"). This lowers the surface free energy of the sealant, which not only improves ejection performance by inkjet devices but also makes it easier to follow fine irregularities, resulting in improved flatness of the coating film. Improved flatness further suppresses the occurrence of pinholes and tends to further reduce display defects.

[0055] When the photocurable compound contains a fluorine-containing compound, the content of the fluorine-containing compound may be, for example, 0.1% by mass or more, preferably 0.5% by mass or more, and more preferably 1% by mass or more, based on the total amount of the photocurable compound. When the photocurable compound contains a fluorine-containing compound, the content of the fluorine-containing compound is preferably 5% by mass or less, and more preferably 2% by mass or less, based on the total amount of the photocurable compound, in order to further improve flatness while suppressing a decrease in refractive index. The content of the fluorine-containing compound may be, for example, 0.1% by mass or more and 2% by mass or less.

[0056] The number of fluoro groups in a fluorine-containing compound may be, for example, one or more, preferably two or more, and more preferably three or more. Furthermore, the number of fluoro groups in a fluorine-containing compound is not particularly limited, but may be, for example, 40 or less, and preferably 30 or less.

[0057] The fluorine atom content relative to the total amount of the fluorine-containing compound may be, for example, 1% by mass or more, preferably 2% by mass or more, and more preferably 5% by mass or more. The above-mentioned effects are more pronounced when a fluorine-containing compound satisfying this content range is used. Alternatively, the fluorine atom content relative to the total amount of the fluorine-containing compound may be, for example, 75% by mass or less, preferably 70% by mass or less, and more preferably 65% ​​by mass or less.

[0058] Fluorine-containing compounds may have radical polymerizable groups. These radical polymerizable groups may be, for example, (meth)acryloyl groups. The number of radical polymerizable groups in a fluorine-containing compound may be one or more. From the viewpoint of obtaining a cured product with a lower glass transition temperature, the number of radical polymerizable groups in a fluorine-containing compound may be one. From the viewpoint of obtaining a cured product with a higher glass transition temperature, the number of radical polymerizable groups in a fluorine-containing compound may be two or more. There is no particular upper limit to the number of radical polymerizable groups in a fluorine-containing compound. The number of radical polymerizable groups in a fluorine-containing compound may be, for example, four or less, and from the viewpoint of obtaining a cured product with superior flexibility, it is preferably three or less, more preferably two or less.

[0059] Examples of fluorine-containing compounds include 2,2,2-trifluoroethyl (meth)acrylate, 2,2,3,3-tetrafluoropropyl (meth)acrylate, 1H,1H,5H-octafluoropentyl (meth)acrylate, 1H,1H,2H,2H-tridecafluorooctyl (meth)acrylate, and 2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9-hexadecafluoro-1,10-decanedi (meth)acrylate.

[0060] <Nitroxyl radical compounds> Nitroxy radical compounds are stable radical-type compounds (RNO·) containing a disubstituted NO· atomic group (N-oxyl group). When a photocurable composition contains a nitroxy radical compound, the number of liquid particles with a particle size of 1 μm or larger in the photocurable composition is reduced, resulting in less nozzle clogging. Furthermore, when a photocurable composition contains a nitroxy radical compound, inkjet ejection stability is improved.

[0061] The nitroxyl radical compound may further contain at least one selected from the group consisting of a hydroxyl group, a mercapto group, a (meth)acryloyl group, and a vinyl (thio) ether group.

[0062] Examples of nitroxyl radical compounds include 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO), 4-hydroxy-2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPOL), 4-acetoxy-2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO-acetate), 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxyl (acetamino-TEMPO), and 4-(meth)acryloyloxy-2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO-(meth)acrylate).

[0063] The nitroxyl radical compound may be, for example, a compound represented by the following formula (5). [ka]

[0064] In the formula, each X independently represents an alkyl group. The alkyl group represented by X may be, for example, an alkyl group having 1 to 6 or 1 to 3 carbon atoms, or a methyl group. Y represents a hydrogen atom, a hydroxyl group, a mercapto group, a (meth)acryloyl group, or a vinyl (thio) ether group.

[0065] The content of the nitroxy radical compound may be 0.05% by mass or more, 0.10% by mass or more, 0.15% by mass or more, or 0.20% by mass or more, based on the total amount of the photocurable composition. The content of the nitroxy radical compound may be 1.5% by mass or less, 1.0% by mass or less, 0.60% by mass or less, or 0.50% by mass or less, based on the total amount of the photocurable composition. The content of the nitroxy radical compound is 0.05 mass% or more and 1.5 mass% or less, 0.05 mass% or more and 1.0 mass% or less, 0.05 mass% or more and 0.60 mass% or less, 0.05 mass% or more and 0.50 mass% or less, 0.10 mass% or more and 1.5 mass% or less, 0.10 mass% or more and 1.0 mass% or less, 0.10 It may be 0.15% to 1.5% by mass, 0.15% to 1.0% by mass, 0.15% to 0.50% by mass, 0.20% to 1.5% by mass, 0.20% to 1.0% by mass, or 0.20% to 0.50% by mass.

[0066] <Reactive Diluent> Reactive diluents are compounds added to photocurable compositions to adjust their viscosity. When a photocurable composition contains a reactive diluent, it results in a composition with lower viscosity at 25°C and facilitates the formation of a cured film with higher transmittance. Furthermore, the inclusion of a reactive diluent improves inkjet ejection stability.

[0067] The reactive diluent may have at least one polymerizable functional group selected from the group consisting of (meth)acryloyl groups and vinyl (thio) ether groups. The reactive diluent may have one or more polymerizable functional groups in its molecule. The total number of polymerizable functional groups in the reactive diluent may be one or more, two or less, for example, one.

[0068] The viscosity of the reactive diluent at 25°C may be 10 mPa·s or less, 8 mPa·s or less, 6 mPa·s or less, 4 mPa·s or less, or 3 mPa·s or less. The viscosity of the reactive diluent at 25°C may be, for example, greater than 0 mPa·s or greater than 1 mPa·s. The viscosity of the reactive diluent at 25°C is measured using a cone-plate viscometer (for example, HB DV3T, cone plate: CPA-40Z, manufactured by Eiko Seiki Co., Ltd.) under conditions of 25°C and 50 rpm.

[0069] The reactive diluent may be a compound having the polymerizable functional group described above and having a viscosity of 10 mPa·s or less at 25°C. Examples of reactive diluents include phenyl(meth)acrylate, methylphenyl(meth)acrylate, ethylphenyl(meth)acrylate, benzyl(meth)acrylate, phenoxyethyl methacrylate, and 2-(2-vinyloxyethoxy)ethyl(meth)acrylate.

[0070] The content of the reactive diluent may be 1% by mass or more, 3% by mass or more, 5% by mass or more, or 8% by mass or more, based on the total amount of the photocurable composition, and may be 20% by mass or less, 15% by mass or less, or 12% by mass or less.

[0071] <Stabilizer> A stabilizer refers to, for example, a polymerization inhibitor. Preferably, the stabilizer is one that does not include stabilizers that are nitroxy radical compounds. Examples of stabilizers include quinone, hydroquinone, methoquinone, tert-butylhydroquinone, 4-tert-butylpyrocatechol, dibutylhydroxytoluene, and phenothiazine.

[0072] The stabilizer content may be, for example, 0.05% by mass or more, 0.10% by mass or more, 0.15% by mass or more, 0.20% by mass or more, or 0.25% by mass or more, based on the total amount of the photocurable composition. The stabilizer content may be 1.5% by mass or less, 1.0% by mass or less, 0.50% by mass or less, or 0.40% by mass or less, based on the total amount of the photocurable composition.

[0073] <Content of monofunctional monomers> The content of a compound having one (meth)acryloyl group and one vinyl (thio) ether group (hereinafter also referred to as "monofunctional monomer") in the photocurable composition may be 50% or more by mass, 60% or more by mass, 70% or more by mass, 80% or more by mass, 90% or more by mass, or 95% or more by mass, based on the total amount of the photocurable composition, and may be 99% or less by mass, 95% or less by mass, 90% or less by mass, 85% or less by mass, or 80% or less by mass. The content of monofunctional monomers may be 50% or more by mass and 100% or less by mass, 60% or more by mass and 100% or less by mass, 70% or more by mass and 100% or less by mass, 80% or more by mass, 90% or more by mass and 100% or less by mass, or 95% or more by mass and 100% or less by mass, based on the total amount of the photocurable composition. When the content of monofunctional monomers is within the above range, a photocurable composition with lower viscosity at 25°C can be obtained, and the storage stability of the photocurable composition is further improved.

[0074] <Content of other ingredients> The content of components other than aromatic monomers, diaryl sulfide compounds, fluorine-containing compounds, nitroxyl radical compounds, stabilizers, reactive diluents, and photopolymerization initiators in the photocurable composition may be 0% to 5% by mass, 0% to 3% by mass, or 0% to 1% by mass, or 0% by mass, based on the total mass of the photocurable composition.

[0075] <Refractive index> The refractive index of the cured film of the photocurable composition at a wavelength of 486 nm is 1.55 or higher. The refractive index is measured under the conditions described in the examples below.

[0076] The refractive index may be 1.56 or higher, 1.58 or higher, 1.60 or higher, 1.62 or higher, 1.64 or higher, 1.66 or higher, or 1.68 or higher, and may be less than 1.90, 1.85 or lower, 1.80 or lower, 1.75 or lower, or 1.70 or lower. The refractive index may be 1.55 or more but less than 1.90, 1.60 or more but 1.80 or less, 1.60 or more but 1.75 or less, 1.60 or more but 1.70 or less, 1.62 or more but 1.80 or less, 1.62 or more but 1.75 or less, 1.62 or more but 1.70 or less, 1.64 or more but 1.80 or less, 1.64 or more but 1.75 or less, 1.64 or more but 1.70 or less, 1.66 or more but 1.80 or less, 1.66 or more but 1.75 or less, 1.66 or more but 1.70 or less, 1.68 or more but 1.80 or less, 1.68 or more but 1.75 or less, or 1.68 or more but 1.70 or less.

[0077] The refractive index can be adjusted to the above-mentioned range by, for example, controlling the type and amount of aromatic monomer used in the photocurable composition, using diaryl sulfide compounds in the photocurable composition and controlling their amount, or by arbitrarily combining these.

[0078] <Number of particles in liquid> The photocurable composition may be liquid at 23°C, and may be liquid at 23°C under normal pressure. The number of liquid particles with a particle size of 1 μm or larger contained in the photocurable composition at 23°C may be 10 particles / ml or less, 8 particles / ml or less, 6 particles / ml or less, 4 particles / ml or less, 2 particles / ml or less, or 1 particle / ml or less. The number of liquid particles may be, for example, 0 to 10 particles / ml. When the number of liquid particles with a particle size of 1 μm or larger contained in the photocurable composition at 23°C is within the above range, inkjet defects due to nozzle clogging are more easily suppressed.

[0079] The number of particles in the liquid of the photocurable composition is measured at 23°C using a liquid particle counter (KS-42B, manufactured by Rion Co., Ltd.). Detailed measurement conditions are as described in the examples below.

[0080] The number of particles in the liquid of the photocurable composition can be adjusted, for example, by using a nitroxy radical compound.

[0081] <Viscosity> The viscosity of the photocurable composition at 25°C may be, for example, 45 mPa·s or less, 40 mPa·s or less, 35 mPa·s or less, or 30 mPa·s or less. The viscosity of the photocurable composition at 25°C may be, for example, 5 mPa·s or more, 10 mPa·s or more, 15 mPa·s or more, 20 mPa·s or more, or 25 mPa·s or more.

[0082] The viscosity of the photocurable composition at 25°C after being stored in a 40°C environment for 120 hours may be, for example, 50 mPa·s or less, 40 mPa·s or less, 30 mPa·s or less, or 25 mPa·s or less. The viscosity of the photocurable composition at 25°C after being stored in a 40°C environment for 120 hours may be, for example, 5 mPa·s or more, 10 mPa·s or more, 15 mPa·s or more, 20 mPa·s or more, or 25 mPa·s or more.

[0083] Viscosity is measured using a cone-plate viscometer (for example, HB DV3T, cone plate: CPA-40Z, manufactured by Eiko Seiki Co., Ltd.) under conditions of 25°C and 50 rpm.

[0084] <Method for producing a photocurable composition> A photocurable composition can be produced, for example, by a method comprising a mixing step of mixing aromatic monomers, a photopolymerization initiator, and other components as needed, and a filtering step of filtering the resulting mixture.

[0085] In the mixing process, each component may be mixed while heating. The mixing temperature in the mixing process may be, for example, 45°C or higher or 55°C or higher, or 75°C or lower or 65°C or lower. The stirring speed during mixing may be, for example, 50 rpm or higher or 100 rpm or higher, or 300 rpm or lower or 200 rpm or lower.

[0086] <Uses of photocurable compositions> The photocurable composition according to this embodiment can be suitably used, for example, to form a light extraction layer (light extraction film).

[0087] [Cured product] One embodiment of the present disclosure is a cured product of the photocurable composition described above. The cured product may be a cured film formed by curing a coating of the photocurable composition. The thickness of the cured film may be, for example, 10 to 30 μm.

[0088] The cured product may contain a polymer of polymerizable monomers including aromatic monomers. The polymerizable monomer may further contain compounds containing polymerizable functional groups in addition to aromatic monomers. Compounds containing polymerizable functional groups may include, for example, compounds having polymerizable functional groups such as (meth)acryloyl groups and vinyl (thio) ether groups (e.g., diaryl sulfides, fluorine-containing compounds, reactive diluents, or nitroxyl radical compounds).

[0089] The cured product can be used, for example, as a component material for light-emitting devices such as a light extraction layer (light extraction film). Figure 1 is a schematic cross-sectional view showing one embodiment of a laminate used in the optical components of a light-emitting device. As shown in Figure 1, in the laminate 10, the light extraction layer 1 is provided between a first layer 2 containing a high refractive index material with a refractive index greater than 1.80 and a second layer 3 containing a low refractive index material with a refractive index less than 1.55. By providing the light extraction layer 1 between the first layer 2 and the second layer 3 with different refractive indices, the decrease in light extraction efficiency due to the phenomenon of total internal reflection of light from the light-emitting layer at the interface with a refractive index difference is suppressed, and as a result, a brightness improvement effect is achieved. The first layer 2 containing the high refractive index material may be, for example, an inorganic layer consisting of a silicon nitride film (refractive index 1.9) or an indium tin oxide (ITO) layer (refractive index 2.1). The second layer 3 containing the low refractive index material may be, for example, a resin layer consisting of a polarizing plate or an optical adhesive (refractive index less than 1.55).

[0090] The cured product can be manufactured by a method including a coating film formation step of forming a coating film of the above-described photocurable composition and a light irradiation step of irradiating the coating film with light. The coating film can be formed using an inkjet device. A known inkjet device (for example, Fujifilm's DMP2850) can be used.

[0091] The light irradiation conditions in the light irradiation process can be appropriately set according to the type of photopolymerization initiator, etc. The irradiation light may include light with a wavelength of 395 nm. The light source is not particularly limited, and for example, an LED lamp (e.g., HOYA UV-LED LIGHT SOURCE H-4MLH200-V1) can be used. The light irradiation conditions are, for example, an integrated light intensity of 2,000 mJ / cm² at a wavelength of 395 nm. 2 ~4,000 mJ / cm 2 The conditions may be as follows: Light irradiation may be carried out under an inert gas atmosphere. Examples of inert gases include nitrogen.

[0092] [Light-emitting display device] One embodiment of the present disclosure is a light-emitting device comprising a cured product of the above-described photocurable composition. The light-emitting device may be an organic EL display. The light-emitting device may include a light extraction layer comprising a cured product of the above-described photocurable composition. [Examples]

[0093] The present disclosure will be specifically described below with reference to examples. However, the present disclosure is not limited to the examples described below.

[0094] <Preparation of photocurable compositions in Examples 1-28 and Comparative Examples 1-3> Photocurable compositions for Examples 1-28 and Comparative Examples 1-3 were prepared using aromatic monomers, diaryl sulfide compounds, fluorine-containing compounds, nitroxyl radical compounds, reactive diluents, photopolymerization initiators, and stabilizers listed in Tables 1-7. The specific procedure is as follows.

[0095] Aromatic monomers, diaryl sulfide compounds, fluorine-containing compounds, nitroxyl radical compounds, reactive diluents, photopolymerization initiators, and stabilizers were weighed according to Tables 1-7 and stirred for 1 hour at 150 rpm and 60°C using a stirrer (three-one motor) to obtain a mixture. The mixture was filtered through a PTFE membrane filter with a pore size of 0.45 μm to obtain a photocurable composition.

[0096] The following is information about the compounds used in this study. [Aromatic monomers] Naphthyl acrylate: Fujifilm Wako Pure Chemical Industries, Ltd. • Naphthalene diacrylate (Ac-N): Air Water Performance Chemicals Naphthalene methyl acrylate (light acrylate NMT-A): Kyoeisha Chemical Co., Ltd. Anthracene methyl methacrylate (9-anthrylmethyl methacrylate): Tokyo Chemical Industry Co., Ltd. Ethoxylated-o-phenylphenol acrylate (A-LEN-10): Shin-Nakamura Chemical Industry Co., Ltd.

[0097] [Diaryl sulfide compounds] • Bis(4-hydroxyphenyl) sulfide: Tokyo Chemical Industry Co., Ltd. • Bis(4-mercaptophenyl) sulfide: Tokyo Chemical Industry Co., Ltd. • Bis(4-methacryloylthiophenyl) sulfide: Tokyo Chemical Industry Co., Ltd. • Bis(4-vinylthiophenyl) sulfide: Alpha Chemistry

[0098] [Fluorine-containing compounds] 2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9-Hexadecafluoro-1,10-decanediaacrylate (LINC-162A): Kyoeisha Chemical Co., Ltd. • 1H,1H,2H,2H-Tridecafluorooctylacrylate (Viscoat 13F): Osaka Organic Chemical Industry Co., Ltd.

[0099] [Nitroxy radical compounds] 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO): Sigma-Aldrich 4-Hydroxy-2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPOL): Sigma-Aldrich 4-Methacryloyloxy-2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO-methacrylate): Sigma-Aldrich

[0100] [Stabilizer] • p-Methoxyphenol (Methoquinone): Seiko Chemical Co., Ltd.

[0101] [Reactive Diluent] • Benzyl acrylate (Viscote #160): Osaka Organic Chemical Industry Co., Ltd. • Benzyl methacrylate (light ester BZ): Kyoeisha Chemical Co., Ltd. Phenoxyethyl methacrylate (light ester PO): Kyoeisha Chemical Co., Ltd. 2-(2-vinyloxyethoxy)ethyl methacrylate (VEEM): Nippon Shokubai Co., Ltd.

[0102] [Photopolymerization initiator] • 2,4,6-trimethylbenzoyl-diphenylphosphine oxide (Omnirad TPO H): IGM Resins • Bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide) (Omnirad 819): IGM Resins • Omnirad 651 (2,2-dimethoxy-2-phenylacetophenone): IGM Resins

[0103] <Rating> [Viscosity and its changes over time (storage stability)] The viscosity of the photocurable composition was measured using a cone-plate viscometer (HB DV3T, manufactured by Eiko Seiki Co., Ltd., cone plate: CPA-40Z) at 25°C and 50 rpm. Similarly, the viscosity of the photocurable composition after 120 hours at 40°C was also measured at 25°C and 50 rpm.

[0104] [Number of particles] Under 23°C conditions, the number of particles in a liquid-based particle counter (KS-42B, manufactured by Rion Co., Ltd.) was used to count the number of particles in the photocurable composition. The measurement conditions were as follows: solvent: acetone for electronics (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.), sample aspiration rate: 10 ml / min, sample aspiration volume: 100 ml, waste liquid discharge rate: 100 ml / min, and number of waste liquid discharges: 3. The cumulative value of the number of particles 1 μm or larger per 1 ml of sample was defined as the number of particles 1 μm or larger (particles / ml).

[0105] [Inkjet ejection stability] A photocurable composition was filled into the inkjet cartridge of an inkjet printer (Fujifilm DMP2850, 16 nozzles). After 30 minutes of ejection at an initial ejection speed of 6.5 (±0.1) m / s and an ejection temperature of 35°C, the ejection status of all 16 nozzles was checked, and the percentage of nozzles with ejection defects was determined. The presence or absence of ejection defects was determined by counting the number of nozzles that did not exhibit any of the following: flight deviation (5° or more), reduced ejection speed (6.0 m / s or less), or failure to eject.

[0106] [Curing the hardened film] Using an inkjet device (Fujifilm DMP2850), a photocurable composition was droplet-impregnated into a 35mm square area to a film thickness of 10μm at an ejection temperature of 35°C. The resulting material was then left to stand in an air atmosphere (23°C, 40%RH) in a cleanroom (Class 1000) under a yellow lamp. Next, under a nitrogen atmosphere, an LED lamp emitting light at a wavelength of 395nm (HOYA UV-LED LIGHT SOURCE H-4MLH200-V1) was used to expose the photosensitive film to a total integrated light intensity of 3,000 mJ / cm² at a wavelength of 395nm. 2 The material was irradiated with light under the specified conditions. This resulted in the acquisition of a cured film.

[0107] [Refractive index] The refractive index of the above-mentioned cured film at a wavelength of 486 nm was measured using a spectroscopic ellipsometer (HORIBA SE-2000).

[0108] [Transmittance] The above cured film was determined to be transparent by measuring its spectral transmittance at 400 nm using a UV-Vis spectrophotometer (Shimadzu Corporation "UV-2550").

[0109] <Evaluation of flatness> On a substrate measuring 70 mm x 70 mm x 0.7 mm thick (alkali-free glass (Corning Eagle XG)), recesses measuring 25 μm x 25 μm x 3 μm thick were created by etching, with 10 μm spacing between them in all directions. Next, a 200 nm SiN film was formed on the recessed substrate using plasma CVD. Then, a resin composition was pattern-coated to a size of 15 mm x 15 mm x 8 μm thick using an inkjet ejector (Musashi Engineering MID500B, solvent-based head "MID head"). Prior to pattern coating, the substrate was cleaned with acetone and isopropanol, respectively, and then cleaned for 5 minutes using a Technovision UV-208 UV ozone cleaning device. After pattern coating, the material was left in a nitrogen atmosphere for 4 minutes at a temperature of 23°C and a relative humidity of 50%. Under the nitrogen atmosphere, an LED lamp (HOYA UV-LED LIGHT SOURCE H-4MLH200-V1) emitting light at a wavelength of 395 nm was used to measure the integrated light intensity of 395 nm light to 1,500 mJ / cm². 2 The resin composition was photocured under the following conditions. Next, the thickness of the cured film was measured using a stylus-type shape measuring device (BRUKER DektakXT) in a direction perpendicular to the direction in which the head moved. The difference between the maximum and minimum thickness in the plane excluding 2 mm from the edge of the cured film was used as the flatness evaluation result.

[0110] [Table 1] [Table 2] [Table 3] [Table 4] [Table 5] [Table 6] [Table 7] [Explanation of Symbols]

[0111] 1...Light extraction layer, 2...First layer, 3...Second layer, 10...Laminate

Claims

1. It comprises an aromatic monomer and a photopolymerization initiator. The aforementioned aromatic monomer is given by the following formula (1) 【Chemistry 1】 It is expressed as, in equation (1), n １ This represents an integer from 1 to 8, and Z １ R represents a single bond, or an oxygen atom, an alkylene group, or a (poly)oxyalkylene group. １ This is a compound that exhibits a hydrogen atom or a methyl group. The refractive index of the cured film at a wavelength of 486 nm is 1.55 or higher. A photocurable composition used for forming a light extraction layer.

2. It comprises a first group containing an anthracene skeleton or a biphenyl skeleton, and a second group containing at least one selected from the group consisting of a (meth)acryloyl group and a vinyl (thio) ether group, The photocurable composition according to claim 1, further comprising an aromatic monomer in which the first group is bonded to the second group via an oxygen atom, an alkylene group, or a (poly)oxyalkylene group, or directly.

3. The photocurable composition according to claim 1 or 2, wherein the content of the aromatic monomer is 50% by mass or more based on the total amount of the photocurable composition.

4. The photocurable composition according to claim 1 or 2, further comprising a diaryl sulfide compound.

5. The photocurable composition according to claim 4, wherein the diaryl sulfide compound has at least one selected from the group consisting of a hydroxyl group, a mercapto group, a (meth)acryloyl group, and a vinyl (thio) ether group.

6. The photocurable composition according to claim 4, wherein the content of the diaryl sulfide compound is 20% by mass or more based on the total amount of the photocurable composition.

7. The photocurable composition according to claim 1 or 2, further comprising a nitroxyl radical compound.

8. The photocurable composition according to claim 7, wherein the nitroxyl radical compound has at least one selected from the group consisting of a hydroxyl group, a mercapto group, a (meth)acryloyl group, and a vinyl (thio) ether group.

9. The photocurable composition according to claim 7, wherein the content of the nitroxyl radical compound is 0.05% by mass or more and 0.60% by mass or less, based on the total amount of the photocurable composition.

10. Further containing a reactive diluent, The reactive diluent has at least one polymerizable functional group selected from the group consisting of (meth)acryloyl groups and vinyl (thio) ether groups, The photocurable composition according to claim 1 or 2, wherein the viscosity of the reactive diluent at 25°C is 10 mPa·s or less.

11. The photocurable composition according to claim 1 or 2, wherein the content of a compound having one polymerizable functional group selected from the group consisting of a (meth)acryloyl group and a vinyl (thio) ether group is 50% by mass or more based on the total amount of the photocurable composition.

12. The photocurable composition according to claim 1 or 2, wherein the photopolymerization initiator is a compound having one phosphorus atom and three aryl groups.

13. A photocurable composition according to claim 1 or 2, comprising a compound having a fluoro group.

14. The photocurable composition according to claim 13, wherein the content of the compound having the fluoro group is 0.1% by mass or more and 5% by mass or less, based on the total mass of the photocurable composition.

15. The photocurable composition is liquid at 23°C. The photocurable composition according to claim 1 or 2, wherein the number of liquid particles with a particle size of 1 μm or more contained in the photocurable composition at 23°C is 10 particles / ml or less.

16. The photocurable composition according to claim 1 or 2, wherein the viscosity at 25°C after storing the photocurable composition in a 40°C environment for 120 hours is 30 mPa·s or less.

17. The photocurable composition according to claim 1 or 2, which is a photocurable composition that can be applied by an inkjet device.

18. A light extraction layer comprising a cured product of the photocurable composition according to claim 1 or 2.

19. A light-emitting device comprising a light extraction layer containing a cured product of the photocurable composition according to claim 1 or 2.

20. The light-emitting display device according to claim 19, wherein it is an organic EL display.

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