WO2024203595A1

WO2024203595A1 - Photocurable resin composition, optical component, method for producing optical component, light emitting device, and method for producing light emitting device

Info

Publication number: WO2024203595A1
Application number: PCT/JP2024/010702
Authority: WO
Inventors: 裕基池上; 祐輔浦岡
Original assignee: パナソニックＩｐマネジメント株式会社
Priority date: 2023-03-30
Filing date: 2024-03-19
Publication date: 2024-10-03

Abstract

The present disclosure provides a photocurable resin composition capable of imparting good bending resistance and low dielectric constant to a cured product. A photocurable resin composition according to the present disclosure contains a photopolymerizable compound (A) and a photopolymerization initiator (B). The photopolymerizable compound (A) contains an amide compound (A1) represented by formula (1). In formula (1), X represents a vinyl group or an alkyl group having 1-4 carbon atoms, Y represents an alkylene group having 2-12 carbon atoms, and Z represents a (meth)acryloyl group, a hydroxy group, an alkylamino group having 1-3 carbon atoms, or a methyl group.

Description

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

The present disclosure relates to a photocurable resin composition, an optical component, a method for manufacturing an optical component, a light-emitting device, and a method for manufacturing a light-emitting device, and more specifically to a photocurable resin composition containing a photopolymerizable compound and a photopolymerization initiator, an optical component made from the photocurable resin composition, a method for manufacturing an optical component using the photocurable resin composition, a light-emitting device including an optical component, and a method for manufacturing a light-emitting device.

Patent Document 1 discloses a photocurable resin composition for electronic devices that contains a curable resin and a polymerization initiator, the curable resin contains a monofunctional cationic polymerizable compound and a polyfunctional cationic polymerizable compound, the monofunctional cationic polymerizable compound contains at least one of a monofunctional aliphatic cationic polymerizable compound and a monofunctional cationic polymerizable compound having an optionally substituted phenoxy group, and the polyfunctional cationic polymerizable compound contains a silicone compound having two or more cationic polymerizable groups, and the photocurable resin composition for electronic devices has a dielectric constant of 3.5 or less measured under conditions of 25°C and 100 kHz.

JP 2021-050290 A

The objective of the present disclosure is to provide a photocurable resin composition capable of imparting good bending resistance and a low relative dielectric constant to the cured product, an optical component made from the photocurable resin composition, a method for manufacturing an optical component using the photocurable resin composition, a light-emitting device including an optical component, and a method for manufacturing a light-emitting device.

The photocurable resin composition according to one embodiment of the present disclosure contains a photopolymerizable compound (A) and a photopolymerization initiator (B). The photopolymerizable compound (A) contains an amide compound (A1) represented by formula (1).

In formula (1), X is a vinyl group or an alkyl group having 1 to 4 carbon atoms, Y is an alkylene group having 2 to 12 carbon atoms, and Z is a (meth)acryloyl group, a hydroxyl group, an alkylamino group having 1 to 3 carbon atoms, or a methyl group.

An optical component according to one embodiment of the present disclosure includes a cured product of the photocurable resin composition.

The method for manufacturing an optical component according to one embodiment of the present disclosure includes discharging the photocurable resin composition by an inkjet method and then irradiating the photocurable resin composition with light to cure it.

The light emitting device according to one aspect of the present disclosure includes a light source and an optical component that transmits light emitted by the light source, and the optical component includes a cured product of the photocurable resin composition.

A method for manufacturing a light-emitting device according to one aspect of the present disclosure is a method for manufacturing a light-emitting device including a light source and an optical component that transmits light emitted by the light source, and includes manufacturing the optical component by the method for manufacturing the optical component.

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

The embodiment of the present disclosure will be described with reference to FIG. 1. The following embodiment is merely a part of the various embodiments of the present disclosure. In addition, the following embodiment can be modified in various ways depending on the design, etc., as long as the object of the present disclosure can be achieved. The figures referred to below are schematic diagrams, and the dimensional ratios of the components in the figures do not necessarily reflect the actual dimensional ratios. The mechanism of action described below is a speculation, and the present disclosure is not bound by the explanation of the mechanism of action below. In the following explanation, "(meth)acryl" is a generic term that is a higher-level concept of "acryl" and "methacryl", and means "acryl" or "(meth)acryl", or "acryl" and "(meth)acryl". For example, "(meth)acryloyl group" means an acryloyl group or a methacryloyl group, or an acryloyl group and a methacryloyl group.

1. Overview The photocurable resin composition according to the embodiment (hereinafter, also referred to as composition (X)) contains a photopolymerizable compound (A) and a photopolymerization initiator (B). The photopolymerizable compound (A) contains an amide compound (A1) represented by formula (1).

Composition (X) can impart good bending resistance and a low dielectric constant to the cured product. For this reason, for example, when the cured product is in sheet form, damage to the cured product when it is bent can be suppressed.

The optical component according to the embodiment contains a cured product of composition (X). This allows the optical component to have good bending resistance and a low dielectric constant.

The optical component in the embodiment is a component having a function of transmitting light. The optical component in the embodiment can be applied to a deformable light-emitting device, such as a foldable display, by increasing the flexibility. The optical component in the embodiment can be applied to a sealing portion of an organic EL light-emitting device in a display or the like. The optical component may be a color resist. That is, for example, a phosphor may be contained in the composition (X), and a color resist in a color filter may be produced from this composition (X). This color filter may be provided in a display device such as an organic EL display or a micro LED display, which is a light-emitting device. In addition, since the optical component in the embodiment has a low relative dielectric constant, it is unlikely to cause a malfunction in a light-emitting device or the like equipped with the optical component. For example, when the light-emitting device is a display equipped with a touch sensor, if the relative dielectric constant of the optical component is high, the touch sensor may malfunction, and the possibility of malfunction increases when the display and the touch sensor are thinned. However, in the present embodiment, the relative dielectric constant of the optical component can be reduced, so that the malfunction of the touch sensor can be suppressed.

The method for manufacturing an optical component according to the embodiment includes discharging composition (X) by an inkjet method and then irradiating composition (X) with light to cure it.

The light-emitting device according to the embodiment includes a light source and an optical component that transmits light emitted by the light source, and the optical component includes a cured product of the composition (X). The light-emitting device is, for example, 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 may include a display device such as a display. The light-emitting device may include a touch sensor. The light-emitting device may be a deformable light-emitting device, such as a foldable display.

The method for manufacturing a light-emitting device according to the embodiment includes manufacturing an optical component in the light-emitting device by a method that includes discharging composition (X) by an inkjet method and then irradiating composition (X) with light to harden it.

The uses and molding methods of composition (X) are not limited to those described above. Composition (X) can be used in a variety of applications. In addition, composition (X) can be molded by various methods and then cured to produce a cured product.

2. Photocurable resin composition The composition (X) contains the photopolymerizable compound (A) and the photopolymerization initiator (B) as described above. The photopolymerizable compound (A) contains an amide compound (A1) represented by formula (1).

The amide compound (A1) allows the cured product of the composition (X) to have good bending resistance and a low dielectric constant. It is presumed that the dielectric constant of the cured product is reduced and the flexibility of the cured product is increased, thereby improving the bending resistance of the cured product, by the fact that Y in the amide compound (A1) is an alkylene group having 2 to 12 carbon atoms. In addition, the amide compound (A1) has nitrogen in its molecule, and when the cured product is produced by stacking it on an inorganic material, the adhesion between the inorganic material and the cured product can be improved. Therefore, when the cured product is folded together with the inorganic material, damage to the cured product is suppressed, which also improves the bending resistance of the cured product. For this reason, when a film (inorganic film) made from an inorganic material such as a passivation layer and a sheet-like optical member made from the composition (X) are stacked on top of each other in a light-emitting device, damage to the optical member can be suppressed even if the optical member is folded together with the inorganic film. In addition, the amide compound (A1) is less likely to cause a large increase in the viscosity of the composition (X).

The number of carbon atoms in the alkylene group Y in formula (1) is preferably 3 or more, and more preferably 5 or more. The number of carbon atoms is more preferably 11 or less.

It is preferable that the amide compound (A1) has at least one of a vinyl group and a (meth)acryloyl group. In this case, the amide compound (A1) can have photoradical polymerizability.

It is preferable that the amide compound (A1) contains at least one of the first amide compound (A11) and the second amide compound (A12). The first amide compound (A11) is a compound having the structure shown in formula (1), in which X is a vinyl group, Y is an alkylene group having 2 to 12 carbon atoms, and Z is a hydroxyl group, an alkylamino group having 1 to 3 carbon atoms, or a methyl group. The second amide compound (A12) is a compound having the structure shown in formula (1), in which X is a methyl group, Y is an alkylene group having 2 to 12 carbon atoms, and Z is a (meth)acryloyl group.

The first amide compound (A11) and the second amide compound (A12) each have only one radically polymerizable functional group in the molecule, and therefore are unlikely to increase cure shrinkage when the composition (X) is cured. Therefore, when the composition (X) is cured on a substrate such as an inorganic film to produce a cured product, the adhesion between the substrate and the cured product is unlikely to decrease. Also, for example, when an inorganic film and a sheet-like optical member made from the composition (X) are stacked, damage to the optical member when the optical member is folded together with the inorganic film can be further suppressed.

The photopolymerizable compound (A) may further contain a compound other than the amide compound (A1). The ratio of the amide compound (A1) to the photopolymerizable compound (A) is preferably 5% by mass or more and 40% by mass or less. If the ratio is 5% by mass or more, the relative dielectric constant of the cured product can be further reduced and the bending resistance can be further improved. If the ratio is 40% by mass or less, there is an advantage that the glass transition temperature of the cured product can be further increased and the heat resistance can be further improved. It is more preferable that the ratio is 7% by mass or more, and even more preferable that the ratio is 10% by mass or more. It is more preferable that the ratio is 35% by mass or less, and even more preferable that the ratio is 30% by mass or less.

When the photopolymerizable compound (A) contains a compound other than the amide compound (A1), the photopolymerizable compound (A) may contain a radical polymerizable compound other than the amide compound (A1).

The photopolymerizable compound (A) may contain a mono(meth)acrylate (A2) having a chain-like saturated hydrocarbon skeleton with 6 to 20 carbon atoms in the molecule. The mono(meth)acrylate (A2) can reduce the dielectric constant of the cured product and increase its flexibility by having a chain-like saturated hydrocarbon skeleton with 6 to 20 carbon atoms in the molecule. Furthermore, the mono(meth)acrylate (A2) has only one radically polymerizable functional group in the molecule, and therefore is less likely to increase the cure shrinkage during curing of the composition (X) and is less likely to cause a decrease in adhesion between the substrate, such as an inorganic film, and the cured product. Furthermore, the mono(meth)acrylate (A2) is less likely to cause a large increase in the viscosity of the composition (X).

The number of carbon atoms in the chain saturated hydrocarbon skeleton in the mono(meth)acrylate (A2) is preferably 8 or more, and more preferably 10 or more. The number of carbon atoms is more preferably 18 or less, and even more preferably 16 or less.

The mono(meth)acrylate (A2) contains, for example, an ester of a monool having a structure in which a hydroxyl group is bonded to one end of a chain-like saturated hydrocarbon skeleton having 6 to 20 carbon atoms, and (meth)acrylic acid. The mono(meth)acrylate (A2) contains, for example, at least one selected from the group consisting of lauryl (meth)acrylate, isostearyl (meth)acrylate, isooctyl (meth)acrylate, isoamyl (meth)acrylate, stearyl (meth)acrylate, isostearyl (meth)acrylate, lauryl (meth)acrylate, isodecyl (meth)acrylate, cetyl (meth)acrylate, isooctyl (meth)acrylate, and tridecyl (meth)acrylate.

The ratio of mono(meth)acrylate (A2) to photopolymerizable compound (A) is preferably 10% by mass or more and 70% by mass or less. If the ratio is 10% by mass or more, the dielectric constant of the cured product can be further reduced and bending resistance can be further improved. If the ratio is 70% by mass or less, there are advantages in that the glass transition temperature of the cured product can be further increased, the heat resistance can be further improved, and outgassing during curing can be reduced. It is more preferable that the ratio is 15% by mass or more, and even more preferable that the ratio is 20% by mass or more. It is more preferable that the ratio is 60% by mass or less, even more preferable that the ratio is 55% by mass or less, and particularly preferable that the ratio is 45% by mass or less.

The photopolymerizable compound (A) may contain a di(meth)acrylate (A3) having a chain-like saturated hydrocarbon skeleton with 6 to 20 carbon atoms in the molecule. The di(meth)acrylate (A3) can reduce the dielectric constant of the cured product and increase its flexibility by having a chain-like saturated hydrocarbon skeleton with 6 to 20 carbon atoms in the molecule. In addition, the di(meth)acrylate (A3) has two radically polymerizable functional groups in the molecule, which can increase the crosslink density of the cured product and increase the glass transition temperature of the cured product, thereby increasing the heat resistance of the cured product. In addition, the di(meth)acrylate (A3) is less likely to cause a large increase in the viscosity of the composition (X).

The number of carbon atoms in the chain saturated hydrocarbon skeleton in the di(meth)acrylate (A3) is preferably 8 or more, and more preferably 10 or more. The number of carbon atoms is more preferably 18 or less, and even more preferably 16 or less.

Di(meth)acrylate (A3) contains, for example, an ester of (meth)acrylic acid and a diol having a structure in which hydroxyl groups are bonded to both ends of a chain-like saturated hydrocarbon skeleton having 6 to 20 carbon atoms. Di(meth)acrylate (A3) is, for example, 1,6-hexanediol di(meth)acrylate, 1,7-heptanediol di(meth)acrylate, 1,8-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, Contains at least one selected from the group consisting of 1,14-tetradecanediol di(meth)acrylate, 1,15-pentadecanediol di(meth)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, and 1,20-icosanediol di(meth)acrylate.

The ratio of di(meth)acrylate (A3) to photopolymerizable compound (A) is preferably 10% by mass or more and 70% by mass or less. If the ratio is 10% by mass or more, the dielectric constant of the cured product can be further reduced and the bending resistance can be further improved. If the ratio is 70% by mass or less, the cure shrinkage during curing of composition (X) can be suppressed. If the ratio is 15% by mass or more, it is more preferable, and if it is 20% by mass or more, it is even more preferable. If the ratio is 60% by mass or less, it is more preferable, if it is 55% by mass or less, and it is particularly preferable if it is 45% by mass or less.

The photopolymerizable compound (A) may contain a mono(meth)acrylate (A4) containing a naphthyl group. The mono(meth)acrylate (A4) can reduce the dielectric constant of the cured product and increase the glass transition temperature by having . In addition, the mono(meth)acrylate (A4) has only one radically polymerizable functional group in the molecule, and therefore is less likely to increase the cure shrinkage during curing of the composition (X) and is less likely to cause a decrease in adhesion between the cured product and a substrate such as an inorganic film. In addition, the mono(meth)acrylate (A4) is less likely to cause a large increase in the viscosity of the composition (X).

The mono(meth)acrylate (A4) contains, for example, a compound represented by the following formula (2):

In formula (2), _X1 is hydrogen or a methyl group, _Y1 is a single bond or an alkylene group having 1 to 6 carbon atoms, _Z1 is a single bond, S or O, _R1 is H or a methyl group, _L1 is a single bond, an ester bond or a thioester bond, and n is 1 or 2, provided that when _L1 is a single bond, n is 1 and m is 6 or 7.

The ratio of mono(meth)acrylate (A4) to photopolymerizable compound (A) is preferably 10% by mass or more and 60% by mass or less. If the ratio is 10% by mass or more, the dielectric constant of the cured product can be further reduced and the heat resistance can be further increased. If the ratio is 60% by mass or less, there is an advantage that the bending resistance of the cured product can be further increased. If the ratio is 15% by mass or more, it is more preferable, and if it is 20% by mass or more, it is even more preferable. If the ratio is 50% by mass or less, it is even more preferable, and if it is 40% by mass or less, it is even more preferable.

The photopolymerizable compound (A) may contain a compound (hereinafter also referred to as compound (A5)) that is not an amide compound (A1), a mono(meth)acrylate (A2), a di(meth)acrylate (A3), or a mono(meth)acrylate (A4). The ratio of compound (A5) to composition (X) is, for example, 0% by mass or more and 40% by mass or less.

Compound (A5) contains at least one of a polyfunctional radically polymerizable compound (A51) (hereinafter also referred to as compound (A51)) having two or more radically polymerizable functional groups in the molecule, and a monofunctional radically polymerizable compound (A52) (hereinafter also referred to as compound (A52)) having only one radically polymerizable functional group in the molecule.

Compound (A52) can increase the reactivity of composition (X). As a result, outgassing from the cured product can be suppressed. Compound (d1) can also increase the crosslink density of the polymer of radically polymerizable compound (A). As a result, the glass transition temperature of the cured product can be increased, thereby improving the heat resistance of the cured product.

Examples of compound (A52) include 1,4-butanediol diacrylate, neopentyl glycol di(meth)acrylate, glycerin triacrylate, 1,3-butylene glycol di(meth)acrylate, 1,4-butanediol oligoacrylate, diethylene glycol diacrylate, 1,6-hexanediol oligoacrylate, triethylene glycol diacrylate, tripropylene glycol diacrylate, dipropylene glycol diacrylate, cyclohexane dimethanol diacrylate, tricyclodecane dimethanol diacrylate, bisphenol A polyethoxy diacrylate, bisphenol F polyethoxy diacrylate, pentaerythritol tetraacrylate, propoxylated (2) neopentyl glycol diacrylate, trimethylol trimethylolpropane triacrylate, tris(2-hydroxyethyl)isocyanurate triacrylate, pentaerythritol triacrylate, ethoxylated (3) trimethylolpropane triacrylate, propoxylated (3) glyceryl triacrylate, pentaerythritol tetraacrylate, ditrimethylolpropane tetraacrylate, ethoxylated (4) pentaerythritol tetraacrylate, dipentaerythritol pentaacrylate, 2-(2-ethoxyethoxy)ethyl acrylate, polyethylene glycol diacrylate, polyethylene glycol dimethacrylate, tripropylene glycol triacrylate, bispentaerythritol hexaacrylate, ethylene glycol diacrylate, ethoxylated 1,6-hexanediol diacrylate, poly Polypropylene glycol diacrylate, 1,4-butanediol diacrylate, tetraethylene glycol diacrylate, 2-n-butyl-2-ethyl-1,3-propanediol diacrylate, hydroxypivalic acid neopentyl glycol diacrylate, hydroxypivalic acid trimethylolpropane triacrylate, ethoxylated phosphoric acid triacrylate, ethoxylated tripropylene glycol diacrylate, neopentyl glycol modified trimethylolpropane diacrylate, stearic acid modified pentaerythritol diacrylate, tetramethylolpropane triacrylate, tetramethylolmethane triacrylate, caprolactone modified trimethylolpropane triacrylate, propoxylated glyceryl triacrylate, tetramethylolmethane tetraacrylate It contains at least one selected from the group consisting of acrylate, ethoxylated pentaerythritol tetraacrylate, dipentaerythritol hexaacrylate, caprolactone-modified dipentaerythritol hexaacrylate, dipentaerythritol hydroxypentaacrylate, neopentyl glycol oligoacrylate, trimethylolpropane oligoacrylate, pentaerythritol oligoacrylate, ethoxylated neopentyl glycol di(meth)acrylate, propoxylated neopentyl glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, ethoxylated trimethylolpropane triacrylate, propoxylated trimethylolpropane triacrylate, and 2-(2-vinyloxyethoxy)ethyl acrylate.

The ratio of compound (A51) to photopolymerizable compound (A) is, for example, 30% by mass or less. The ratio of the total of compounds having two or more radically polymerizable functional groups in the molecule, including compound (A51), to photopolymerizable compound (A) is, for example, 10% by mass or more and 70% by mass or less.

Compound (A52) is, for example, tetrahydrofurfuryl acrylate, isobornyl acrylate, 2-hydroxyethyl acrylate, 4-hydroxybutyl acrylate, isobutyl acrylate, t-butyl acrylate, 2-methoxyethyl acrylate, methoxytriethylene glycol acrylate, 2-ethoxyethyl acrylate, 3-methoxybutyl acrylate, ethoxyethyl acrylate, butoxyethyl acrylate, ethoxydiethylene glycol acrylate, methoxydixylethyl acrylate, ethyl diglycol acrylate, cyclic trimethylolpropane formal monoacrylate, imino diethyl acrylate, ethoxylated succinic acid acrylate, trifluoroethyl acrylate, ω-carboxypolycaprolactone monoacrylate, cyclohexyl acrylate, 2-(2-ethoxyethoxy)ethyl acrylate, diethylene glycol monobutyl ether acrylate, 3,3,5-trimethylcyclohexanol acrylate, caprolactone acrylate, ethoxylated (4) nonylphenol acrylate, methoxypolyethylene glycol (350) monoacrylate, methoxypolyethylene glycol (550) monoacrylate, phenoxyethyl acrylate, cyclohexyl (meth)acrylate, dicyclohexyl tetrahydrofurfuryl (meth)acrylate, benzyl acrylate, methylphenoxyethyl acrylate, 4-t-butylcyclohexyl acrylate, caprolactone-modified tetrahydrofurfuryl acrylate, tribromophenyl acrylate, ethoxylated tribromophenyl acrylate, 2-phenoxyethyl acrylate, ethylene oxide adduct of 2-phenoxyethyl acrylate, propylene oxide adduct of 2-phenoxyethyl acrylate, dicyclopentanyl acrylate, phenoxydiethylene glycol acrylate, 2-hydroxy-3-phenoxypropane It contains at least one compound selected from the group consisting of acryloyl acrylate, 1,4-cyclohexane dimethanol monoacrylate, 3-methacryloyloxymethyl cyclohexene oxide, 3-acryloyloxymethyl cyclohexene oxide, vinylmethyl oxazolidinone, acryloyl morpholine, 4-morpholine acrylate, dimethyl acrylamide, dimethyl methacrylamide, dimethyl aminopropyl acrylamide, dimethyl aminopropyl methacrylamide, diethyl acrylamide, diethyl methacrylamide, N-vinyl-2-pyrrolidone, and pentamethyl piperidyl methacrylate.

The ratio of compound (A52) to photopolymerizable compound (A) is, for example, 30% by mass or less. In addition, the total ratio of compounds having only one radically polymerizable functional group in the molecule, including compound (A52) in radically polymerizable compound (A), to composition (X) is, for example, 30% by mass or more and 90% by mass or less.

The photopolymerizable compound (A) may further contain a photocationically polymerizable compound (A6). The ratio of the photocationically polymerizable compound (A6) to the photopolymerizable compound (A) is, for example, 0% by mass or more and 30% by mass or less.

The photopolymerization initiator (B) will be described. The photopolymerization initiator (B) preferably contains a photoradical polymerization initiator (B1). The photoradical polymerization initiator (B1) contains at least one compound selected from the group consisting of, for example, aromatic ketones, acylphosphine oxide compounds, aromatic onium salt compounds, organic peroxides, thio compounds (thioxanthone compounds, thiophenyl group-containing compounds, etc.), hexaarylbiimidazole compounds, oxime ester compounds, borate compounds, azinium compounds, metallocene compounds, active ester compounds, compounds having a carbon-halogen bond, and alkylamine compounds.

The ratio of the photoradical polymerization initiator (B1) to the photoradical polymerizable compound in the photopolymerizable compound (A) is preferably 6% by mass or more. In this case, the composition (X) can have good photocurability and can also have good photocurability under an atmospheric environment. This ratio is more preferably 7% by mass or more, and even more preferably 8% by mass or more. This ratio is, for example, 30% by mass or less, preferably 20% by mass or less, and even more preferably 18% by mass or less.

The photoradical polymerization initiator (B1) may contain a photoradical polymerization initiator having photobleaching properties. In this case, the cured product of the composition (X) may have good light transmittance. The ratio of the photoradical polymerization initiator having photobleaching properties to the radically polymerizable compound is preferably 3 mass% or more. This ratio is more preferably 7 mass% or more, and even more preferably 8 mass% or more. This ratio is, for example, 30 mass% or less, preferably 25 mass% or less, and even more preferably 20 mass% or less.

The photoradical polymerization initiator having photobleaching properties contains at least one of, for example, an acylphosphine oxide-based photoinitiator and a compound having photobleaching properties among oxime ester-based photoinitiators.

The photoradical polymerization initiator (B1) may contain a component having a sensitizer skeleton in the molecule. The sensitizer skeleton includes, for example, at least one of a 9H-thioxanthen-9-one skeleton and an anthracene skeleton. In other words, it is preferable that the photoradical polymerization initiator (B1) includes a component having at least one of a 9H-thioxanthen-9-one skeleton and an anthracene skeleton.

The composition (X) may contain a polymerization accelerator in addition to the photoradical polymerization initiator (B1). The polymerization accelerator contains, for example, an amine compound such as ethyl p-dimethylaminobenzoate, 2-ethylhexyl p-dimethylaminobenzoate, methyl p-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, or butoxyethyl p-dimethylaminobenzoate. Note that the components that the polymerization accelerator may contain are not limited to those mentioned above.

In addition, when the photopolymerizable compound (A) contains a photocationic polymerizable compound (A6), it is preferable that the photopolymerization initiator (B) contains a photocationic polymerization initiator (B2).

The composition (X) preferably does not contain a solvent or the solvent content is 1% by mass or less. In this case, outgassing derived from the solvent is unlikely to occur from the composition (X) and the cured product of the composition (X). In addition, a drying process for removing the solvent from the composition (X) and the cured product during the production of optical components and light-emitting devices can be eliminated. A drying process for removing the solvent from at least one of the composition (X) and the cured product may be performed. In this case, at least one of the heating temperature and the heating time in the drying process can be reduced. Therefore, outgassing can be unlikely to occur from the optical components without reducing the production efficiency of the optical components and light-emitting devices. Furthermore, when the composition (X) is molded by ejecting it, especially by the inkjet method, the thickness is unlikely to decrease due to the evaporation of the solvent from the composition (X) after molding, and therefore the thickness of the optical components is unlikely to decrease. Therefore, the thickness of the optical components can be secured as large as possible while ejecting the composition (X) by the inkjet method to mold it. The content of the solvent is preferably 0.5% by mass or less, more preferably 0.3% by mass or less, and particularly preferably 0.1% by mass or less. It is particularly preferable that the composition (X) does not contain a solvent or contains only a solvent that is inevitably mixed in.

Composition (X) may further contain any additives other than those mentioned above, such as inorganic fillers, moisture absorbents, dispersants, and silane coupling agents, to the extent that the object of the present disclosure is not significantly impeded.

When composition (X) contains inorganic filler (C), inorganic filler (C) is preferably nano-sized. In this case, the cured product can have a high refractive index while maintaining good transparency (visible light transmittance) of the cured product. Nano-sized means that the average particle size is 1 nm or more and 1000 nm or less. The average particle size of inorganic filler (C) is preferably 30 nm or less, and more preferably 20 nm or less. In addition, this average particle size is preferably 5 nm or more, and more preferably 10 nm or more. Note that this average particle size is the median diameter calculated from the measurement results by dynamic light scattering method, that is, the cumulative 50% diameter (D50). Note that the Nanotrac NanotracWave series from Microtrac Bell Co., Ltd. can be used as a measuring device.

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

In this embodiment, the composition (X) may have a low viscosity. Therefore, the moldability of the composition (X) is good. For example, the composition (X) may be molded by discharging it by an inkjet method. When producing a cured product or an optical part, etc. from the composition (X), it is preferable to mold the composition (X) by discharging it by an inkjet method. That is, the composition (X) is preferably for inkjet molding. In this case, the cured product and the optical part of the composition (X) can be produced with good positional accuracy. In addition, compared to molding by a printing method involving contact such as a screen printing method, when the composition (X) is molded by discharging it by an inkjet method, foreign matter is less likely to be mixed into the composition (X) and its cured product, and therefore the yield when manufacturing the optical part is less likely to deteriorate.

It is preferable that the viscosity of composition (X) at 40°C is 16 mPa·s or less. In this case, no matter what the viscosity of composition (X) is 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 in particular, it can be easily molded by discharging it by an inkjet method. In addition, since the viscosity of composition (X) can be reduced without significantly heating it, it is possible to make it difficult for the composition of composition (X) to change due to the volatilization of the components in composition (X). It is also preferable that this viscosity is 1 mPa·s or more, and more preferably 5 mPa·s or more.

It is also preferable that the viscosity of composition (X) at 25°C is 50 mPa·s or less. It is more preferable that the viscosity of composition (X) at 25°C is 40 mPa·s or less, even more preferable that it is 30 mPa·s or less, and particularly 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, more preferably 10 mPa·s or more, and even more preferably 20 mPa·s or more. In these cases, composition (X) can be easily molded at room temperature, and in particular can be easily molded by the inkjet method.

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 explained in detail in the Examples section below.

The rate of outgassing generated when the cured product of composition (X) is heated at 110°C for 30 minutes is preferably 25 ppm or less. In other words, by increasing the curability of composition (X) according to this embodiment, it is preferable that the rate of outgassing generated from the cured product is 25 ppm or less. In this case, outgassing is less likely to occur from the cured product. This makes it possible to make it difficult for voids due to outgassing to occur in a light-emitting device that includes an optical component made of the cured product, for example. This makes it difficult for water and oxygen to reach the light-emitting element through voids, making it difficult for the light-emitting element to deteriorate due to water and oxygen. It is particularly preferable for this rate of outgassing to be 15 ppm.

The reduction in the proportion of outgassing generated from the cured product of composition (X) can be achieved by appropriately adjusting the composition of photopolymerizable compound (A) within the range described above. The method for measuring the proportion of outgassing will be described in detail in the examples below.

The glass transition temperature of the cured product of the composition (X) is preferably 60°C or higher. In other words, the composition (X) preferably has the property of curing to become a cured product with a glass transition temperature of 60°C or higher. In this case, the cured product can have good heat resistance. Therefore, for example, when the cured product is subjected to a process involving an increase in temperature, the cured product is less likely to deteriorate. Therefore, for example, when an inorganic film (e.g., passivation layer 6) that overlaps an optical component is produced by a deposition method such as a plasma CVD method, the optical component is less likely to deteriorate even if the optical component is heated. In addition, by increasing the heat resistance, the optical component can be adapted to applications such as vehicle-mounted applications that have strict requirements for heat resistance. The glass transition temperature of the cured product is more preferably 65°C or higher, even more preferably 70°C or higher, and particularly preferably 75°C or higher. This glass transition temperature of the cured product can be achieved by appropriately adjusting the composition of the photopolymerizable compound (A) within the range described above.

The total light transmittance according to JIS K7361-1 of a 10 μm-thick cured product made from composition (X) is preferably 98.0% or more, and more preferably 99.0% or more. This total light transmittance of the cured product can be achieved by appropriately adjusting the composition of composition (X) within the range described above.

The dielectric constant of the cured product made from the composition at 25°C and a measurement frequency of 100 kHz is preferably 3.0 or less. In this case, when the cured product is applied to an optical component in a light-emitting device, the operational reliability of the light-emitting device can be improved. In particular, when the cured product is applied to an optical component in a light-emitting device equipped with a touch panel, malfunction of the touch sensor can be suppressed. The dielectric constant of the cured product is more preferably 2.9 or less, and even more preferably 2.8 or less. This dielectric constant of the cured product can be achieved by appropriately adjusting the composition of composition (X) within the range described above.

3. Optical component and light-emitting device An example of the structure of a light-emitting device 1 including an optical component made from the composition (X) will be described. The light-emitting device 1 includes a light source and an optical component that transmits light emitted by the light source. For example, the light-emitting device 1 includes a light-emitting element 4, and a sealant 5 and a passivation layer 6 that cover the light-emitting element 4. In this case, the light-emitting element 4 is the light source, the sealant 5 is the optical component, and the passivation layer 6 is an inorganic film. The sealant 5 and the passivation layer 6 overlap each other.

The light-emitting element 4 includes, for example, a light-emitting diode. The light-emitting diode includes, for example, at least one of an organic EL element (organic light-emitting diode) and a micro light-emitting diode. 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. Note that EL is an abbreviation for electroluminescence.

An example of the structure of the light-emitting device 1 will be described with reference to FIG. 1. This light-emitting device 1 is a top-emission type. The light-emitting device 1 includes a support substrate 2, a transparent substrate 3 that faces the support substrate 2 with a gap therebetween, a light-emitting element 4 on the surface of the support substrate 2 that faces the transparent substrate 3, and a passivation layer 6 and a sealing material 5 that cover the light-emitting element 4.

The support substrate 2 is made of, for example, but not limited to, a resin material. The transparent substrate 3 is made of a light-transmitting material. The transparent substrate 3 is, for example, a glass substrate or a transparent resin substrate. The light-emitting element 4 includes, for example, a pair of

electrodes

41, 43 and an organic light-emitting layer 42 between the

electrodes

41, 43. The organic light-emitting layer 42 includes, for example, a hole injection layer 421, a hole transport layer 422, an organic light-emitting layer 423, and an electron transport layer 424, and these layers are stacked in the above order.

The light-emitting device 1 includes a plurality of light-emitting elements 4, which form an array 9 (hereinafter referred to as element array 9) on a support substrate 2. The element array 9 also includes a partition 7. The partition 7 is on the support substrate 2 and separates two adjacent light-emitting elements 4. The partition 7 is fabricated, for example, by forming a photosensitive resin material using a photolithography method. The element array 9 also includes connection wiring 8 that electrically connects the electrodes 43 and electron transport layers 424 of adjacent light-emitting elements 4. The connection wiring 8 is provided on the partition 7.

The passivation layer 6 corresponds to an inorganic film. The passivation layer 6 is preferably made of silicon nitride or silicon oxide, and is particularly preferably made of silicon nitride. 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 covers the element array 9 while being in direct contact with the element array 9, thereby covering the light-emitting element 4. The second passivation layer 62 is disposed on the opposite side of the element array 9 with respect to the first passivation layer 61, and a gap is provided between the second passivation layer 62 and the first passivation layer 61. The sealant 5 is filled between the first passivation layer 61 and the second passivation layer 62. That is, the first passivation layer 61 is interposed between the light-emitting element 4 and the sealant 5 covering the light-emitting element 4.

Furthermore, a second sealing material 52 is filled between the second passivation layer 62 and the transparent substrate 3. The second sealing material 52 is made of, for example, a transparent resin material. There are no particular limitations on the material of the second sealing material 52. The material of the second sealing material 52 may be the same as or different from the sealing material 5.

The method for producing the encapsulant 5 using the composition (X) and the method for producing the light emitting device 1 are described below.

In this embodiment, it is preferable to eject the composition (X) by an inkjet method to form a film, and then irradiate the composition (X) with ultraviolet light to harden it, thereby producing the sealing material 5. In this embodiment, the composition (X) can be ejected and shaped by an inkjet method.

When discharging the composition (X) by the inkjet method, if the composition (X) has a sufficiently low viscosity at room temperature, for example, if the viscosity at 25°C is 30 mPa·s or less, particularly 16 mPa·s or less, the composition (X) can be molded by discharging it by the inkjet method without heating it. If the viscosity of the composition (X) is reduced by heating, the composition (X) may be heated and then discharged by the inkjet method to be molded. As described above, if the viscosity of the composition (X) at 40°C is particularly 16 mPa·s or less, the viscosity of the composition (X) can be reduced by simply heating it slightly, and this reduced-viscosity composition (X) can be discharged by the inkjet method. The heating temperature of the composition (X) is, for example, 20°C or higher and 50°C or lower.

More specifically, for example, first, the support substrate 2 is prepared. On one surface of the support substrate 2, partition walls 7 are fabricated by photolithography using, for example, a photosensitive resin material. Next, a plurality of light-emitting elements 4 are provided on one surface of the support substrate 2. The light-emitting elements 4 can be fabricated by an appropriate method such as a vapor deposition method or a coating method. In particular, it is preferable to fabricate the light-emitting elements 4 by a coating method such as an inkjet method. In this way, an element array 9 is fabricated on the support substrate 2.

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

Next, the composition (X) is ejected onto the first passivation layer 61, for example, by an inkjet method, and shaped to form a coating film. By applying the inkjet method to both the production of the light-emitting element 4 and the formation of the coating film, the production efficiency of the light-emitting device 1 can be particularly improved. Next, the coating film of the composition (X) is cured by irradiating it with light, to produce the encapsulant 5.

When irradiating composition (X) with light, composition (X) may be irradiated with light in an atmosphere containing oxygen, such as an air atmosphere, or composition (X) may be irradiated with light in an inert atmosphere, such as a nitrogen atmosphere.

Next, a second passivation layer 62 is provided on the sealing material 5. The second passivation layer 62 can be produced by a deposition method such as plasma CVD.

Next, a photocurable resin material is applied to one surface of the support substrate 2 so as to cover the second passivation layer 62, and then the transparent substrate 3 is placed on top of this resin material. The transparent substrate 3 is, for example, a glass substrate or a transparent resin substrate.

Next, ultraviolet light is applied from the outside toward the transparent substrate 3. The ultraviolet light passes through the transparent substrate 3 and reaches the photocurable resin material. This causes the photocurable resin material to harden, producing the second sealing material 52.

The thickness of the sealing material 5 is, for example, 1 μm or more and 50 μm or less. The thickness of the sealing material 5 is more preferably 20 μm or less, and even more preferably 15 μm or less. In this case, by thinning the sealing material 5, the light emitting device 1 can be thinned, and it is also possible to obtain a flexible light emitting device 1, i.e., a bendable light emitting device. In order to effectively suppress moisture from entering the light emitting element 4 by the sealing material 5, the thickness of the sealing material 5 is preferably 3 μm or more, more preferably 5 μm or more, and even more preferably 8 μm or more.

The thickness of the passivation layer 6 overlapping the sealing material 5 is, for example, 0.1 μm or more and 2 μm or less. When the passivation layer 6 includes the first passivation layer 61 and the second passivation layer 62 as described above, it is preferable that the thickness of each of the first passivation layer 61 and the second passivation layer 62 is 0.1 μm or more and 2 μm or less.

The light-emitting device 1 may be a deformable light-emitting device 1 such as a foldable display. In the embodiment, the sealing material 5 is flexible and has high adhesion to the passivation layer 6, which is an inorganic film, so that even if the light-emitting device 1 is bent or otherwise deformed, damage to the sealing material 5 can be suppressed.

The light emitting device may be equipped with a touch sensor. In this embodiment, the relative dielectric constant of the sealing material 5 can be reduced, which can prevent the touch sensor from malfunctioning.

4. Aspects The photocurable resin composition according to the first aspect contains a photopolymerizable compound (A) and a photopolymerization initiator (B). The photopolymerizable compound (A) contains an amide compound (A1) represented by formula (1).

In this embodiment, the photocurable resin composition can impart good bending resistance and a low dielectric constant to the cured product.

In the second embodiment, the amide compound (A1) in the first embodiment contains at least one of a first amide compound (A11) and a second amide compound (A12). The first amide compound (A11) is a compound having a structure shown in formula (1), in which X is a vinyl group, Y is an alkylene group having 2 to 12 carbon atoms, and Z is a hydroxy group, an alkylamino group having 1 to 3 carbon atoms, or a methyl group. The second amide compound (A12) is a compound having a structure shown in formula (1), in which X is a methyl group, Y is an alkylene group having 2 to 12 carbon atoms, and Z is a (meth)acryloyl group.

This embodiment can further improve the bending resistance of the cured product.

In the third embodiment, the photopolymerizable compound (A) in the first or second embodiment further contains a mono(meth)acrylate (A2) having a linear saturated hydrocarbon skeleton with 6 to 20 carbon atoms in the molecule.

This embodiment can further reduce the dielectric constant of the cured product and further increase its flexibility.

In a fourth embodiment, in any one of the first to third embodiments, the photopolymerizable compound (A) contains a di(meth)acrylate (A3) having a chain-like saturated hydrocarbon skeleton with 6 to 20 carbon atoms in the molecule.

This embodiment can further reduce the dielectric constant of the cured product, increase its flexibility, and increase the glass transition temperature of the cured product.

In a fifth embodiment, in any one of the first to fourth embodiments, the photopolymerizable compound (A) further contains a mono(meth)acrylate (A4) having a naphthyl group in the molecule.

This embodiment can further reduce the dielectric constant of the cured product, increase the glass transition temperature, and further improve bending resistance.

In a sixth aspect, in any one of the first to fifth aspects, the viscosity at 25°C is 50 mPa·s or less.

In this embodiment, the photocurable resin composition has good moldability, and it may be possible to mold it by ejecting it using the inkjet method.

In a seventh aspect, in any one of the first to sixth aspects, the photocurable resin composition has a cured product with a relative dielectric constant of 3.0 or less at 25°C and a measurement frequency of 100 kHz.

In an eighth aspect, in any one of the first to seventh aspects, the photocurable resin composition is for use in producing optical components.

According to this aspect, the optical component can have good bending resistance and a low dielectric constant.

The optical component according to the ninth aspect includes a cured product of the photocurable resin composition according to any one of the first to eighth aspects.

The method for producing an optical component according to the tenth aspect includes ejecting the photocurable resin composition according to any one of the first to eighth aspects by an inkjet method, and then irradiating the photocurable resin composition with light to cure it.

This method allows optical components to be manufactured with high positional accuracy and reduces the yield.

The light emitting device according to the eleventh aspect includes a light source and an optical component that transmits light emitted by the light source, and the optical component includes a cured product of the photocurable resin composition according to any one of the first to eighth aspects.

The method for manufacturing a light-emitting device (1) according to the twelfth aspect is a method for manufacturing a light-emitting device including a light source and an optical component that transmits light emitted by the light source, and includes manufacturing the optical component by the method according to the tenth aspect.

According to this embodiment, the optical components in the light emitting device (1) can be manufactured with high positional precision, and the yield is less likely to deteriorate.

1. Preparation of Compositions Compositions of the Examples and Comparative Examples were prepared by mixing the components shown in the following table. Details of the components shown in the table are as follows.
Amide compound #11: The compound shown in the following formula (2-(acetylamino)ethyl 2-propenoate). Manufactured by NOF Corporation. Product name: AA-22.

- Amide compound #12: The compound shown in the formula below (N-[3-(dimethylamino)propyl]acrylamide). Manufactured by KJ Chemicals Co., Ltd. Product name: DMAPAA.

- Amide compound #13: The compound shown in the formula below (N-(2-hydroxyethyl)acrylamide). Manufactured by KJ Chemicals Co., Ltd. Product name: HEAA.

- Amide compound #14: The compound shown in the formula below (N-n-octylacrylamide). Manufactured by KJ Chemicals Co., Ltd. Product name: NOAM.

- Amide compound #15: The compound shown in the formula below (N-dodecylacrylamide). Manufactured by Tokyo Chemical Industry Co., Ltd.

- Amide compound #21: N,N-dimethylacrylamide. Manufactured by KJ Chemicals Co., Ltd. Product name: DMAA.
- Amide compound #22: N-isopropylacrylamide, manufactured by KJ Chemicals Co., Ltd. Product name: NIPAM.
- Mono (meth) acrylate # 11: Lauryl acrylate, manufactured by Kyoeisha Chemical Co., Ltd. Product name: Light Acrylate LA.
- Mono(meth)acrylate #12: Isostearyl acrylate, manufactured by Osaka Organic Chemical Industry Co., Ltd. Product name: ISTA.
- Mono(meth)acrylate #21: Butyl acrylate, manufactured by Fujifilm Wako Pure Chemical Industries, Ltd. Product name: BA.
Mono(meth)acrylate #22: Methoxy-polyethylene glycol acrylate, manufactured by Kyoeisha Chemical Co., Ltd. Product name: Light Acrylate 130A.
-Di(meth)acrylate #11: 1,12-dodecanediol dimethacrylate. Manufactured by Tomoe Engineering Co., Ltd. Product name: SR262.
-Di(meth)acrylate #12: 1,10-decanediol diacrylate, manufactured by Shin-Nakamura Chemical Co., Ltd. Product name: A-DOD-N.
-Di(meth)acrylate #21: 1,4-butanediol diacrylate. Manufactured by Tomoe Engineering Co., Ltd. Product name: SR213.
Mono(meth)acrylate #31: Compound represented by the following formula (1-naphthylmethylacrylate), manufactured by Kyoeisha Chemical Co., Ltd. Product name: Light Acrylate NMT-A.

- Multifunctional (meth)acrylate #1: Pentaerythritol triacrylate, manufactured by Kyoeisha Chemical Co., Ltd. Product name PE-3A.
- Multifunctional (meth)acrylate #2: Glycerin triacrylate, manufactured by Toagosei Co., Ltd. Product name: M930.
Photopolymerization initiator #1: acylphosphine oxide-based photoradical polymerization initiator, manufactured by IGM Resins BV, product name Omnirad TPO H.
Photopolymerization initiator #2: Oxime ester-based photoradical polymerization initiator, manufactured by BASF Japan Ltd. Product name: Irgacure OXE04.

2. Evaluation test (1) Dielectric constant A coating film of the composition having a thickness of 10 μm was prepared on an aluminum substrate having dimensions of 80 mm × 40 mm × 1 mmt. This coating film was irradiated under a nitrogen atmosphere using a Unijet E075IIHD (peak wavelength 395 nm) manufactured by Ushio Inc. under conditions of an irradiation intensity of 0.5 W/ ^cm2 and an accumulated light quantity of 1.5 J/ ^cm2 to cure the coating film. Using an LCR meter (manufactured by Agilent, "E4980A") and a jig (16034 test fixture), the dielectric constant of the cured coating film was measured by the electrode contact method under conditions of an atmospheric temperature of 25°C and a measurement frequency of 100 kHz.

(2) Storage Modulus A coating film was prepared by applying the composition, and the coating film was photocured by irradiating the coating film with ultraviolet light under a nitrogen atmosphere at an irradiation intensity of 3 W/cm ² and an accumulated light quantity of 15 J/cm ² using a Unijet E075IIHD (peak wavelength 395 nm) manufactured by Ushio Inc., to prepare a film having a thickness of 500 μm. The storage modulus at 25° C. of a sample cut out from the film was measured using a viscoelasticity measuring device (manufactured by Hitachi High-Tech Science Corporation, model number DMA7100).

(3) Viscosity at 25° C. and Viscosity at 40° C. The viscosity of the composition at 25° C. and at 40° C. was measured using a rheometer (manufactured by Anton Paar Japan, Model DHR-2) at a shear rate of 1000 ^s .

(4) Inkjet properties The composition was placed in a cartridge of an inkjet printer (manufactured by Fujifilm Corporation, model DMP2831), 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. As a result, the following evaluation was performed: when the droplets did not separate, it was rated as "A"; when the satellites separated from the original droplets and then merged with the original droplets to form one droplet again, it was rated as "B"; and when the satellites separated from the original droplets and did not merge, it was rated as "C."

(5) Curability The composition was measured with an infrared spectrometer (Agilent Cary 610 FTIR Microscope System, manufactured by Agilent Technologies, Inc.) to obtain an IR spectrum.

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

The peak intensity of the absorption of the acryloyl group appearing at 810 cm ^-1 _was measured in each of the two IR spectra. The reduction rate of the reactive functional group in the composition before and after irradiation with ultraviolet light was calculated using the formula {1-( _I0 - _I1 )/ _I0 } x 100(%) from the peak intensity _I0 for the coating film and the peak intensity I1 for the cured product. The result was taken as the reaction rate, and the reaction rate was evaluated as "A" for 90% or more, "B" for 80% or more but less than 90%, and "C" for less than 80%.

(6) Outgassing Evaluation The outgassing when the cured product of the composition was heated was sampled by the headspace method and measured by gas chromatography. In detail, 100 mg of the composition was first placed in a headspace vial with a volume of 22 mL. Next, the composition was cured by irradiating the composition with light having a peak wavelength of 395 nm under a nitrogen atmosphere using a UV irradiator (manufactured by Ushio Electric Co., Ltd., model number Unijet E075IIHD) under conditions of irradiation intensity of 0.5 W/cm ² and accumulated light amount of 1.5 J/cm ² , and then the vial was sealed. Next, the composition was heated at 110°C for 30 minutes, and then the gas phase portion in the vial was introduced into a gas chromatograph for analysis. As a result, the concentration of the outgassing generated from the composition was specified based on the peak area of the obtained gas chromatogram. The concentration of the outgassing is the volume fraction of the outgassing in the gas phase of the vial relative to the volume of the vial (22 mL).

The outgassing concentration was determined using toluene as the standard substance. Specifically, two standard samples with toluene concentrations of 1000 ppm and 100 ppm were prepared by volatilizing toluene in a vial. Each standard sample was introduced into a gas chromatograph for analysis. From the peak areas of the two chromatograms obtained in this way, the relationship between peak area and concentration was determined, and the above-mentioned outgassing concentration was determined based on these results.

The results were evaluated as follows:
A: Concentration 30 ppm or less.
B: Concentration of more than 30 ppm and less than 50 ppm.
C: Concentration exceeding 50 ppm.

(7) Adhesion A silicon oxynitride film (SiON film), which is an inorganic film, was formed on a slide glass by CVD to a thickness of 1 μm. A coating film was formed by applying a composition to a thickness of 10 μm on this inorganic film, and this coating film was irradiated with light having a peak wavelength of 395 nm under a nitrogen atmosphere using a UV irradiator (manufactured by Ushio Electric Co., Ltd., model number Unijet E075IIHD) under conditions of irradiation intensity of 0.5 W/cm ² and accumulated light amount of 1.5 J/cm ^2. This coating film was pulled in the 90 degree direction with an autograph (manufactured by Shimadzu Corporation, model number AGS-X) to measure the peel strength. A peel strength of 100 mN/cm or more was rated as "A", a peel strength of 50 mN/cm or more was rated as "B", a peel strength of 20 mN/cm or more was rated as "C", and a peel strength of less than 20 mN/cm was rated as "D".

(8) Flexibility A silicon oxynitride film (SiON film), which is an inorganic film, was formed to a thickness of 1 μm on a polyimide film, which is a substrate, by a CVD method. The composition was applied to the inorganic film to a thickness of 10 μm to form a coating film, and the coating film was irradiated with light having a peak wavelength of 395 nm under a nitrogen atmosphere using a UV irradiator (manufactured by Ushio Electric Co., Ltd., model number Unijet E075IIHD) under conditions of an irradiation intensity of 0.5 W/cm ² and an accumulated light amount of 1.5 J/cm ² to produce a film having a thickness of 10 μm. As a result, an evaluation sample including a substrate, an inorganic film, and a film was produced.

This evaluation sample was subjected to a test in which it was repeatedly bent 100,000 times under conditions in which the radius of curvature of the bent portion was 1.5 mm, 2.0 mm, and 3.0 mm.

As a result, the evaluation sample was rated as "A" if there was no peeling or cracking in the film after testing under any of the conditions, "B" if there was no peeling or cracking in the film after testing under the bending radius conditions of 2.0 mm and 3.0 mm, and peeling and cracking in the film after testing under the bending radius condition of 1.5 mm, and "C" if there was no peeling or cracking in the film after testing under the bending radius condition of 3.0 mm, but peeling and cracking in the film after testing under the bending radius conditions of 1.5 mm and 2.0 mm.

(9) Glass Transition Temperature A coating film was prepared by applying the composition, and the coating film was photocured by irradiating the coating film under a nitrogen atmosphere with light having a peak wavelength of 395 nm using a UV irradiator (manufactured by Ushio Inc., model number E075IIHD) under conditions of an irradiation intensity of 3 W/ ^cm2 and an accumulated light quantity of 15 J/ ^cm2 , thereby preparing a film having a thickness of 500 μm. The glass transition temperature of a sample cut out from the film was measured using a viscoelasticity measuring device (manufactured by Hitachi High-Tech Science Corporation, model number DMA7100).

1 Light emitting device 4 Light emitting element (light source)
5. Sealing material (optical parts)

Claims

A photopolymerizable compound (A);
A photopolymerization initiator (B),
The photopolymerizable compound (A) contains an amide compound (A1) represented by formula (1),

In formula (1), X is a vinyl group or an alkyl group having 1 to 4 carbon atoms, Y is an alkylene group having 2 to 12 carbon atoms, and Z is a (meth)acryloyl group, a hydroxy group, an alkylamino group having 1 to 3 carbon atoms, or a methyl group.
Photocurable resin composition.
the amide compound (A1) contains at least one of a first amide compound (A11) and a second amide compound (A12),
The first amide compound (A11) is a compound having a structure represented by formula (1), in which X is a vinyl group, Y is an alkylene group having from 2 to 12 carbon atoms, and Z is a hydroxy group, an alkylamino group having from 1 to 3 carbon atoms, or a methyl group.
The second amide compound (A12) is a compound having a structure represented by formula (1), in which X is a methyl group, Y is an alkylene group having from 2 to 12 carbon atoms, and Z is a (meth)acryloyl group.
The photocurable resin composition according to claim 1.
The photopolymerizable compound (A) further contains a mono(meth)acrylate (A2) having a chain-like saturated hydrocarbon skeleton having 6 to 20 carbon atoms in the molecule.
The photocurable resin composition according to claim 1 .
The photopolymerizable compound (A) contains a di(meth)acrylate (A3) having a chain-like saturated hydrocarbon skeleton having 6 to 20 carbon atoms in the molecule.
The photocurable resin composition according to claim 1.
The photopolymerizable compound (A) further contains a mono(meth)acrylate (A4) having a naphthyl group in the molecule.
The photocurable resin composition according to claim 1.
The viscosity at 25°C is 50 mPa·s or less.
The photocurable resin composition according to claim 1.
The dielectric constant of the cured product at 25° C. and a measurement frequency of 100 kHz is 3.0 or less.
The photocurable resin composition according to claim 1 .
For manufacturing optical components.
The photocurable resin composition according to claim 1.
A cured product of the photocurable resin composition according to any one of claims 1 to 8.
Optical components.
A method for producing a photocurable resin composition according to claim 1 , comprising discharging the photocurable resin composition according to claim 1 by an inkjet method, and then irradiating the photocurable resin composition with light to cure the composition.
A method for manufacturing optical components.
A light source and an optical component that transmits light emitted by the light source, the optical component including a cured product of the photocurable resin composition according to any one of claims 1 to 8.
Light emitting device.
A method for manufacturing a light emitting device comprising a light source and an optical component that transmits light emitted by the light source, the method comprising the steps of:
The optical component is manufactured by the method of claim 10.
A method for manufacturing a light emitting device.