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

Abstract

The present disclosure provides a photocurable resin composition having good wettability with respect to an inorganic material and good adhesiveness with respect to an inorganic material of a cured product. The photocurable resin composition contains a photopolymerizable compound (A) and a photopolymerization initiator (B). The photopolymerizable compound (A) contains a heterocyclic compound (A1) having a heterocycle containing at least two hetero atoms.

Description

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

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

[0002] Patent Document 1 discloses a photocurable resin composition for electronic devices containing a curable resin and a polymerization initiator, wherein the curable resin contains a monofunctional radical polymerizable compound and a polyfunctional radical polymerizable compound, the monofunctional radical polymerizable compound containing at least one selected from the group consisting of monofunctional radical polymerizable compounds having an adamantyl skeleton and monofunctional radical polymerizable compounds having a fluorine-substituted hydrocarbon group, and the photocurable resin composition for electronic devices has a dielectric constant of 3.5 or less when measured under conditions of 25°C and 100 kHz. According to Patent Document 1, this photocurable resin composition for electronic devices has excellent low outgassing properties and heat resistance after curing, and also has a low dielectric constant after curing.

[0003] International Publication No. 2021 / 085241

[0004] An object of the present disclosure is to provide a photocurable resin composition that can have good wettability to inorganic materials and good adhesion of the cured product to inorganic materials, an optical component that can be produced from the photocurable resin composition, a method for manufacturing an optical component using the photocurable resin composition, a light-emitting device that includes an optical component, and a method for manufacturing a light-emitting device.

[0005] A photocurable resin composition according to one embodiment of the present disclosure includes a photopolymerizable compound (A) and a photopolymerization initiator (B). The photopolymerizable compound (A) includes a heterocyclic compound (A1) having a heterocycle containing two or more heteroatoms.

[0006] An optical component according to one aspect of the present disclosure includes a cured product of the photocurable resin composition.

[0007] A method for manufacturing an optical component according to one aspect 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.

[0008] A 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, the optical component including a cured product of the photocurable resin composition.

[0009] 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 comprising a light source and an optical component that transmits light emitted by the light source, and includes manufacturing the optical component using a method for manufacturing the optical component.

[0010] FIG. 1 is a schematic cross-sectional view showing a light-emitting device according to an embodiment of the present disclosure.

[0011] An embodiment of the present disclosure will be described with reference to FIG. 1 . Note that the following embodiment is merely a portion of various embodiments of the present disclosure. Furthermore, 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 conjecture, and the present disclosure is not bound by the explanation of the mechanism of action below. In the following description, "(meth)acryl" is a generic term that is a higher-level concept of "acryl" and "(meth)acryl", and refers to "acryl" or "(meth)acryl", or "acryl" and "(meth)acryl". For example, a "(meth)acryloyl group" refers to an acryloyl group or a methacryloyl group, or an acryloyl group and a methacryloyl group.

[0012] 1. Overview The photocurable resin composition according to the embodiment contains a photopolymerizable compound (A) and a photopolymerization initiator (B). The photopolymerizable compound (A) contains a heterocyclic compound (A1) having a heterocycle containing two or more heteroatoms.

[0013] The composition (X) has good wettability to inorganic materials, and the cured product of the composition (X) can have good adhesion to inorganic materials. Therefore, the composition (X) can be easily formed into a thin film on an inorganic material, and when the composition (X) is cured on an inorganic material, the thin-film cured product of the composition (X) can adhere well to the inorganic material. Furthermore, this can prevent the cured product from breaking when the thin-film cured product is bent.

[0014] The optical component according to the embodiment includes a cured product of the composition (X), and therefore the optical component can have good bending resistance.

[0015] The optical component in the embodiments is a component that has the function of transmitting light. The optical component in the embodiments can be applied to a deformable light-emitting device, such as a foldable display, due to its increased flexibility. The optical component in the embodiments can be applied to, for example, a sealing portion of an organic EL light-emitting device in a display or the like. The optical component may also be a color resist. That is, for example, a phosphor may be contained in composition (X), and a color resist for 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.

[0016] The method for producing an optical component according to the embodiment includes discharging composition (X) by an inkjet method to form, for example, a film, and then irradiating the formed composition (X) with light to cure it.

[0017] 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 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.

[0018] The manufacturing method of the light-emitting device according to the embodiment includes manufacturing an optical component of the light-emitting device by a method including ejecting composition (X) by an inkjet method to form, for example, a film, and then irradiating the formed composition (X) with light to cure it.

[0019] The uses and molding methods of composition (X) are not limited to those described above. Composition (X) can be used for various purposes. In addition, composition (X) can be molded into an appropriate shape by various methods and then cured to produce a cured product.

[0020] 2. Photocurable Resin Composition As described above, the composition (X) contains the photopolymerizable compound (A). The photopolymerizable compound (A) contains a radical polymerizable compound.

[0021] The photopolymerizable compound (A) contains a heterocyclic compound (A1) having a heterocycle containing two or more heteroatoms. The molecule of the heterocyclic compound (A1) can have high polarity due to the heterocycle containing two or more heteroatoms. Therefore, the wettability of the composition (X) to inorganic materials is improved. When the inorganic material contains a highly polar material such as an inorganic nitride, the wettability of the composition (X) to inorganic materials can be particularly improved. Furthermore, the heterocyclic compound (A1) can improve the adhesion of the cured product to inorganic materials.

[0022] The heterocyclic compound (A1) preferably contains a monofunctional radically polymerizable compound having only one radically polymerizable functional group per molecule, which can further enhance the adhesion of the cured product to inorganic materials.

[0023] The heterocyclic compound (A1) may contain at least one selected from the group consisting of, for example, a compound having an oxazoline ring, a compound having a morpholine ring, a compound having a pyrrolidone ring, and a compound having a piperidine ring, etc. The heterocyclic compound (A1) may also contain compounds other than those mentioned above.

[0024] The heterocyclic compound (A1) preferably contains at least one selected from the group consisting of a compound (A11) represented by formula (1), a compound (A12) represented by formula (2), and a compound (A13) represented by formula (3).

[0025]

[0026] In formula (1), X １ is O or a single bond, X ２ is O or CH ２ , X ３ is C=O or CH ２ , X ４ is CH ３ Or H, X ５ is C═O or a single bond, and X １ , X ２ and X ３ At least one of them contains O and X １ , X ２ , X ３ and X ５ At least two of the groups contain O.

[0027]

[0028] In formula (2), Y １ is N or CH, Y ２ is C═O or a single bond.

[0029]

[0030] In formula (3), Z １ is NH, O or S, Z ２ is S, O or a single bond, Z ３ is C═O or a single bond.

[0031] Each of compound (A11), compound (A12), and compound (A13) can particularly enhance the wettability of composition (X) to inorganic materials. Furthermore, each of compound (A11), compound (A12), and compound (A13) has a low viscosity, which can contribute to lowering the viscosity of composition (X). Furthermore, each of compound (A11), compound (A12), and compound (A13) has a moderately low volatility, which makes it less likely to reduce the storage stability of composition (X) and less likely to cause outgassing from the cured product. Furthermore, each of compound (A11), compound (A12), and compound (A13) has good reactivity, which can contribute to improving the curability of composition (X).

[0032] The heterocyclic compound (A1) preferably contains both the compound (A11) represented by formula (1) and the compound (A12) represented by formula (2). In this case, the wettability and curability of the composition (X) to inorganic materials, as well as the adhesion of the cured product to inorganic materials, can be improved in a balanced manner.

[0033] When the heterocyclic compound (A1) contains the compound (A11) and the compound (A12), the ratio of the compound (A11) to the heterocyclic compound (A1) is preferably equal to or less than the ratio of the compound (A12) to the heterocyclic compound (A1), and more preferably lower than the ratio of the compound (A12) to the heterocyclic compound (A1). In this case, the above-mentioned effect may occur more significantly. Specifically, the ratio of the compound (A11) to the total of the compound (A11) and the compound (A12) is preferably 50% by mass or less, more preferably 40% by mass or less, and even more preferably 30% by mass or less. Furthermore, this ratio is preferably 5% by mass or more, more preferably 7% by mass or more, and even more preferably 10% by mass or more.

[0034] The total proportion of the compounds (A11), (A12), and (A13) relative to the heterocyclic compound (A1) is preferably 50% by mass or more, more preferably 60% by mass or more, and even more preferably 70% by mass or more. The heterocyclic compound (A1) may contain only at least one selected from the group consisting of the compounds (A11), (A12), and (A13).

[0035] When the heterocyclic compound (A1) contains the compound (A11) and the compound (A12), the ratio of the total of the compound (A11) and the compound (A12) to the heterocyclic compound (A1) is preferably 40% by mass or more. In this case, the above-mentioned effect can be obtained more significantly. This ratio is more preferably 50% by mass or more, and even more preferably 60% by mass or more. The heterocyclic compound (A1) may contain only the compound (A11) and the compound (A12).

[0036] The photopolymerizable compound (A) may further contain a heterocyclic compound (A3) having a heterocycle containing only one heteroatom. The compound (A3) may contain, for example, at least one compound selected from the group consisting of N-vinylcaprolactam, N-vinylpyrrolidone, tetrahydrofurfuryl acrylate, and (3-ethyloxetan-3-yl)methyl acrylate. When the photopolymerizable compound (A) contains the compound (A3), the ratio of the compound (A3) to the photopolymerizable compound (A) is preferably 70% by mass or less, more preferably 50% by mass or less, and even more preferably 40% by mass or less. The ratio of the compound (A3) to the photopolymerizable compound (A) is, for example, 5% by mass or more, 10% by mass or more, or 15% by mass or more.

[0037] The photopolymerizable compound (A) may further contain a (meth)acrylate (A2) that does not have a heterocycle in the molecule.

[0038] When the photopolymerizable compound (A) contains a (meth)acrylate (A2), the (meth)acrylate (A2) may contain a mono(meth)acrylate (A21) having a linear saturated hydrocarbon skeleton having from 6 to 20 carbon atoms in the molecule. The mono(meth)acrylate (A21) can enhance the flexibility of the cured product by having a linear saturated hydrocarbon skeleton having from 6 to 20 carbon atoms in the molecule. Furthermore, the mono(meth)acrylate (A21) has only one radically polymerizable functional group in the molecule, which makes it less likely to increase cure shrinkage during curing of the composition (X) and less likely to cause a decrease in adhesion between the inorganic material and the cured product. Furthermore, the mono(meth)acrylate (A21) makes it less likely to cause a significant increase in the viscosity of the composition (X).

[0039] The number of carbon atoms in the chain saturated hydrocarbon skeleton of the mono(meth)acrylate (A21) is more preferably 8 or more, and even more preferably 10 or more. The number of carbon atoms is more preferably 18 or less, and even more preferably 16 or less.

[0040] The mono(meth)acrylate (A21) contains, for example, an ester of (meth)acrylic acid and a monool having a structure in which a hydroxyl group is bonded to one end of a linear saturated hydrocarbon skeleton having from 6 to 20 carbon atoms. The mono(meth)acrylate (A21) contains, for example, at least one member 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.

[0041] The ratio of the mono(meth)acrylate (A21) to the (meth)acrylate (A2) is preferably 5% by mass or more and 60% by mass or less. If the ratio is 5% by mass or more, the bending resistance of the cured product can be further improved. If the ratio is 60% by mass or less, there are advantages in that the glass transition temperature of the cured product can be increased, thereby further improving heat resistance, and that improved curability can reduce outgassing from the cured product. If the ratio is 10% 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 55% by mass or less, it is more preferable, and if it is 50% by mass or less, it is even more preferable.

[0042] When the (meth)acrylate (A2) contains a mono(meth)acrylate (A21), the ratio of the (meth)acrylate (A2) to the photopolymerizable compound (A) is preferably 20% by mass or more and 80% by mass or less. If the ratio is 20% by mass or more, the bending resistance of the cured product can be further improved. If the ratio is 80% by mass or less, there are advantages in that the glass transition temperature of the cured product is increased, thereby further improving heat resistance, and the improved curability can reduce outgassing from the cured product. A ratio of 25% by mass or more is more preferable, and a ratio of 30% by mass or more is even more preferable. A ratio of 75% by mass or less is more preferable, and a ratio of 70% by mass or less is even more preferable.

[0043] The ratio of the mono(meth)acrylate (A21) to the photopolymerizable compound (A) is preferably 20% by mass or more and 60% by mass or less. If the ratio is 20% by mass or more, the bending resistance of the cured product can be further improved. If the ratio is 60% by mass or less, there are advantages in that the glass transition temperature of the cured product can be increased, the heat resistance can be further improved, the curability can be improved, and outgassing during curing can be reduced. If the ratio is 22% by mass or more, it is more preferable, and if it is 25% by mass or more, it is even more preferable. If the ratio is 50% by mass or less, it is more preferable, and if it is 40% by mass or less, it is even more preferable.

[0044] The (meth)acrylate (A2) may contain only the mono(meth)acrylate (A21), may contain the mono(meth)acrylate (A21) and a compound (A22) different from the mono(meth)acrylate (A21), or may contain only the compound (A22) different from the mono(meth)acrylate (A21).

[0045] The compound (A22) different from the mono(meth)acrylate (A21) contains at least one selected from the group consisting of polyfunctional (meth)acrylates (A221) having two or more radically polymerizable functional groups in one molecule, and monofunctional (meth)acrylates (A222) having only one radically polymerizable functional group in one molecule.

[0046] The polyfunctional (meth)acrylate (A221) can increase the reactivity of the composition (X). As a result, outgassing from the cured product can be suppressed. The polyfunctional (meth)acrylate (A221) can also increase the crosslink density of the polymer of the photopolymerizable 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.

[0047] Examples of the polyfunctional (meth)acrylate (A221) include 1,5-pentanediol di(meth)acrylate, neopentyl glycol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,7-heptanediol di(meth)acrylate, 1,8-octanediol di(meth)acrylate, 1,9-nonanediol di(meth)acrylate, 1,10-decanediol di(meth)acrylate, 1,11-undecanediol di(meth)acrylate, 1,12-dodecanediol di(meth)acrylate, 1,13-tridecanediol di(meth)acrylate, 1,14-tetradecanediol di(meth)acrylate, 1,15-pentadecanediol di(meth)acrylate, and 1,16-hexadecanediol di(meth)acrylate. ol di(meth)acrylate, 1,17-heptadecanediol di(meth)acrylate, 1,18-octadecanediol di(meth)acrylate, 1,19-nonadecanediol di(meth)acrylate, 1,20-icosanediol di(meth)acrylate, 1,21-heneicosanediol di(meth)acrylate, 1,22-docosanediol di(meth)acrylate, 1,23-triicosanediol di(meth)acrylate, 1,24-tetracosanediol di(meth)acrylate, 1,25-pentacosanediol 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, cyclohexanedimethanol diacrylate, tricyclodecane dimethanol diacrylate, bisphenol A polyethoxydiacrylate, bisphenol F polyethoxydiacrylate, pentaerythritol tetraacrylate, propoxylated (2) neopentyl glycol diacrylate, trimethylolpropane triacrylate, tris(2-hydroxyethyl)isocyanurate triacrylate, pentaerythritol triacrylate, ethoxylated (3) trimethylolpropane triacrylate, propoxylated (3) glycerin aryl 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, 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, ethoxylated pentaerythritol tetraacrylate, dipenta The composition contains at least one selected from the group consisting of erythritol 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.

[0048] The ratio of the polyfunctional (meth)acrylate (A221) to the photopolymerizable compound (A) is, for example, 5% by mass or more. This ratio is more preferably 10% by mass or more, and even more preferably 15% by mass or more. Furthermore, this ratio is, for example, 60% by mass or less. This ratio is more preferably 50% by mass or less, and even more preferably 40% by mass or less.

[0049] Examples of the monofunctional (meth)acrylate (A222) include tetrahydrofurfuryl acrylate, isobornyl acrylate, 2-hydroxyethyl acrylate, 4-hydroxybutyl acrylate, butyl 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, imide 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, and the like. acrylate, caprolactone acrylate, ethoxylated (4) nonylphenol acrylate, methoxypolyethylene glycol monoacrylate, methoxypolyethylene glycol (350) monoacrylate, methoxypolyethylene glycol (550) monoacrylate, phenoxyethyl acrylate, cyclohexyl (meth)acrylate, dicyclopentanyl (meth)acrylate, 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-phenoxypropyl acrylate, 1,It contains at least one compound selected from the group consisting of 4-cyclohexanedimethanol monoacrylate, 3-methacryloyloxymethyl cyclohexene oxide, and 3-acryloyloxymethyl cyclohexene oxide.

[0050] The monofunctional (meth)acrylate (A222) may contain a compound (A2221) that does not contain a heterocycle in the molecule but has a nitrogen atom. The compound (A2221) may contain at least one selected from the group consisting of compounds having a dimethylamino group, such as dimethylacrylamide, dimethylmethacrylamide, dimethylaminopropylacrylamide, and dimethylaminopropylmethacrylamide; compounds having a diethylamino group, such as diethylacrylamide and diethylmethacrylamide; and N-isopropylacrylamide.

[0051] The ratio of the monofunctional (meth)acrylate (A222) to the photopolymerizable compound (A) is, for example, 5% by mass or more. This ratio is more preferably 7% by mass or more, and even more preferably 10% by mass or more. Furthermore, this ratio is, for example, 30% by mass or less. This ratio is more preferably 25% by mass or less, and even more preferably 20% by mass or less.

[0052] The photopolymerizable compound (A) may further contain compounds other than those described above, as long as the object of this embodiment is not excessively hindered. For example, the photopolymerizable compound (A) may further contain a radical polymerizable compound having no (meth)acryloyl group. The photopolymerizable compound (A) may further contain a photocationic polymerizable compound. The photopolymerizable compound (A) may further contain a compound having a silicon atom but no heterocycle in the molecule.

[0053] The photopolymerization initiator (B) will be described. In an embodiment, the photopolymerization initiator (B) contains a photoradical polymerization initiator. The photopolymerization initiator (B) contains at least one compound selected from the group consisting of, for example, aromatic ketones, acylphosphine oxide compounds, aromatic onium salt compounds, organic peroxides, thio compounds (such as thioxanthone compounds and thiophenyl group-containing compounds), hexaarylbiimidazole compounds, oxime ester compounds, borate compounds, azinium compounds, metallocene compounds, active ester compounds, compounds having a carbon-halogen bond, and alkylamine compounds.

[0054] The amount of photopolymerization initiator (B) per 100 parts by mass of photopolymerizable compound (A) is preferably 6 parts by mass or more. In this case, composition (X) can have good photocurability and can also have good photocurability under atmospheric conditions. This amount is more preferably 7 parts by mass or more, and even more preferably 8 parts by mass or more. This amount is, for example, 30 parts by mass or less, preferably 20 parts by mass or less, and even more preferably 18 parts by mass or less.

[0055] The photopolymerization initiator (B) 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 amount of the photoradical polymerization initiator having photobleaching properties per 100 parts by mass of the photopolymerizable compound (A) is preferably 3 parts by mass or more. This amount is more preferably 7 parts by mass or more, and even more preferably 8 parts by mass or more. Furthermore, this amount is, for example, 30 parts by mass or less, preferably 25 parts by mass or less, and even more preferably 20 parts by mass or less.

[0056] The photoradical polymerization initiator having photobleachability contains, for example, at least one of an acylphosphine oxide-based photoinitiator and a compound having photobleachability among oxime ester-based photoinitiators.

[0057] The photopolymerization initiator (B) may contain a component having a sensitizer skeleton in the molecule. The sensitizer skeleton includes, for example, at least one of a 9H-thioxanthen-9-one skeleton and an anthracene skeleton. That is, the photopolymerization initiator (B) preferably includes a component having at least one of a 9H-thioxanthen-9-one skeleton and an anthracene skeleton.

[0058] The composition (X) may contain a polymerization accelerator in addition to the photopolymerization initiator (B). The polymerization accelerator contains, for example, an amine compound such as ethyl p-dimethylaminobenzoate, 2-ethylhexyl p-dimethylaminobenzoate, methyl p-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, or butoxyethyl p-dimethylaminobenzoate. However, the components that can be contained in the polymerization accelerator are not limited to those mentioned above.

[0059] It is preferable that the composition (X) further contains a silicone-based surface tension modifier (C). The surface tension modifier is also called a surface conditioner. The silicone-based surface tension modifier (C) can effectively reduce the surface tension of the composition (X), thereby contributing to improving the wettability of the composition (X) with inorganic materials. The silicone-based surface tension modifier (C) can also contribute to improving the adhesion of the cured product with inorganic materials. Furthermore, the silicone-based surface tension modifier (C) is less likely to generate substances that adversely affect light-emitting elements, etc.

[0060] The silicone-based surface tension modifier (C) may contain a commercially available product, for example, at least one selected from the group consisting of BYK products under the trade names BYK377, BYK333, BYK307, BYK322, BYK333, and BYK-UV3535.

[0061] The ratio of the silicone surface tension modifier (C) to the composition (X) is preferably 0.01% by mass or more. In this case, the effect of the silicone surface tension modifier (C) can be significantly exhibited. This ratio is more preferably 0.03% by mass or more. It is also preferable that this ratio is 1% by mass or less. In this case, there is an advantage that bleeding out of the silicone surface tension modifier (C) from the cured product can be suppressed. This ratio is more preferably 0.7% by mass or less, and even more preferably 0.5% by mass or less.

[0062] Note that composition (X) may contain a surface tension modifier other than the silicone-based surface tension modifier (C) within a range that does not excessively impair the objectives of the present disclosure. However, acrylic surface tension modifiers are less effective than the silicone-based surface tension modifier (C). Furthermore, fluorine-based surface tension modifiers may generate hydrofluoric acid, which may adversely affect organic EL devices. For this reason, it is preferable that composition (X) does not contain any surface tension modifier other than the silicone-based surface tension modifier (C), or that the proportion of surface tension modifiers other than the silicone-based surface tension modifier (C) in composition (X) is lower than the proportion of the silicone-based surface tension modifier (C) in composition (X).

[0063] Preferably, composition (X) does not contain a solvent or contains 1% by mass or less of a solvent. In this case, outgassing due to the solvent is unlikely to occur from composition (X) and the cured product of composition (X). Furthermore, a drying step for removing the solvent from composition (X) and the cured product during the production of optical components and light-emitting devices can be eliminated. A drying step for removing the solvent from at least one of composition (X) and the cured product may be included. In this case, at least one of a lower heating temperature and a shorter heating time can be achieved in the drying step. Therefore, outgassing from the optical components can be reduced without reducing the production efficiency of optical components and light-emitting devices. Furthermore, when composition (X) is molded by ejecting it, particularly using an inkjet method, the thickness of the molded composition (X) is unlikely to decrease due to the evaporation of the solvent, and therefore the thickness of the optical components is unlikely to decrease. Therefore, the thickness of the optical components can be maximized while ejecting and molding composition (X) using an inkjet method. The solvent content is more preferably 0.5% by mass or less, even more preferably 0.3% by mass or less, and particularly preferably 0.1% by mass or less. It is particularly preferred that the composition (X) does not contain a solvent or contains only an unavoidably mixed solvent.

[0064] The composition (X) may further contain any additives other than those described above, such as an inorganic filler, a moisture absorbent, a dispersant, and a silane coupling agent, as long as the object of the present disclosure is not significantly impaired.

[0065] When composition (X) contains an inorganic filler, the inorganic filler is preferably nano-sized. In this case, the cured product can have a high refractive index while maintaining good transparency (visible light transmittance). Nano-sized means that the average particle size is 1 nm or more and 1000 nm or less. The average particle size of the inorganic filler is preferably 30 nm or less, more preferably 20 nm or less. Furthermore, this average particle size is preferably 5 nm or more, more preferably 10 nm or more. Note that this average particle size is the median diameter calculated from the measurement results using dynamic light scattering, i.e., the cumulative 50% diameter (D50). Note that the Nanotrac NanotracWave series from Microtrac Bell Co., Ltd. can be used as a measuring device.

[0066] In this embodiment, composition (X) can be used to manufacture an optical component. An optical component is a component that is arranged on the path of light in an optical system. In this embodiment, composition (X) can be preferably used to manufacture an optical component that transmits light. However, the use of composition (X) is not limited to the manufacture of optical components, and composition (X) can be applied to various uses that utilize its properties.

[0067] 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) can be molded by ejecting it using an inkjet method. When producing a cured product, optical components, or the like from the composition (X), it is preferable to mold the composition (X) by ejecting it using an inkjet method. That is, the composition (X) is preferably designed for inkjet molding. In this case, a cured product of the composition (X) and an optical component can be produced with high positional accuracy. Furthermore, compared to molding using a printing method involving contact, such as a screen printing method, when the composition (X) is molded by ejecting it using an inkjet method, foreign matter is less likely to be mixed into the composition (X) and its cured product, and therefore the yield when producing optical components is less likely to deteriorate.

[0068] The viscosity of composition (X) at 40°C is preferably 16 mPa·s or less. In this case, regardless of the viscosity of composition (X) at room temperature, it is possible to lower the viscosity by slightly heating composition (X). Therefore, composition (X) can be easily molded by heating, and can be easily molded by ejecting it by an inkjet method in particular. Furthermore, since the viscosity of composition (X) can be lowered without significantly heating it, changes in the composition of composition (X) due to volatilization of components in composition (X) can be made less likely. It is also preferable that this viscosity is 1 mPa·s or more, and more preferably 5 mPa·s or more.

[0069] It is also preferable that the viscosity of composition (X) at 25°C is 40 mPa s or less. It is more preferable that the viscosity of composition (X) at 25°C is 30 mPa s or less, and even more preferable that it is 28 mPa s or less. It is also preferable that this viscosity is 1 mPa s or more, more preferably 5 mPa s or more, 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 can be easily molded, particularly by an inkjet method.

[0070] Such a low viscosity of composition (X) can be achieved by appropriately adjusting the composition of photopolymerizable compound (A) within the range described above. The method and conditions for measuring the viscosity of composition (X) will be described in the Examples section below.

[0071] The surface tension of composition (X) is preferably 30 mN / m or less. In this case, the composition can have particularly good wettability with inorganic materials. The surface tension is more preferably 29 mN / m or less, and even more preferably 28 mN / m or less. The surface tension is, for example, 20 mN / m or more, 22 mN / m or more, or 24 mN / m or more. The method and conditions for measuring the surface tension will be explained in the Examples section below.

[0072] As a result of the increased flexibility of the cured product of composition (X), the storage modulus of the cured product is preferably 4.5 GPa or less. In this case, breakage of the cured product when bent can be further suppressed. A storage modulus of 4.0 GPa or less is more preferable, and a storage modulus of 3.5 GPa or less is even more preferable. The storage modulus is, for example, 1.5 GPa or more. The method and conditions for measuring the storage modulus will be explained in the Examples section below.

[0073] The total light transmittance of a 10 μm-thick cured product produced from composition (X) is preferably 98.0% or more, and more preferably 99.0% or more, according to JIS K7361-1. This total light transmittance of the cured product can be achieved by appropriately adjusting the composition of composition (X) within the range described above.

[0074] 3. Optical Component and Light-Emitting Device An example of the structure of a light-emitting device 1 including an optical component made from 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 material. The sealant 5 and the passivation layer 6 overlap each other.

[0075] 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.

[0076] An example of the structure of a 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 facing the support substrate 2 with a gap therebetween, a light-emitting element 4 on the surface of the support substrate 2 facing the transparent substrate 3, and a passivation layer 6 and a sealing material 5 that cover the light-emitting element 4.

[0077] 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, which are stacked in the aforementioned order.

[0078] The light-emitting device 1 includes a plurality of light-emitting elements 4, and the plurality of light-emitting elements 4 form an array 9 (hereinafter referred to as element array 9) on a support substrate 2. The element array 9 also includes a partition wall 7. The partition wall 7 is located on the support substrate 2 and separates two adjacent light-emitting elements 4. The partition wall 7 is fabricated, for example, by 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 to each other. The connection wiring 8 is provided on the partition wall 7.

[0079] The passivation layer 6 corresponds to an inorganic material. The passivation layer 6 is preferably made of silicon nitride or silicon oxide, and particularly preferably made of silicon nitride. In the example shown in FIG. 1 , the passivation layer 6 includes a first passivation layer 61 and a second passivation layer 62. The first passivation layer 61 is in direct contact with the element array 9 and covers the element array 9, thereby covering the light-emitting element 4. The second passivation layer 62 is disposed on the opposite side of the first passivation layer 61 from the element array 9, and a gap is provided between the second passivation layer 62 and the first passivation layer 61. The encapsulant 5 is filled between the first passivation layer 61 and the second passivation layer 62. In other words, the first passivation layer 61 is interposed between the light-emitting element 4 and the encapsulant 5 covering the light-emitting element 4.

[0080] 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.

[0081] A method for producing the encapsulant 5 using the composition (X) and a method for producing the light emitting device 1 will be described.

[0082] 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 cure it, thereby producing the sealing material 5. In this embodiment, the composition (X) can be ejected and molded by an inkjet method.

[0083] When ejecting composition (X) by the inkjet method, if 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, composition (X) can be ejected by the inkjet method without heating and molded. If the viscosity of composition (X) is reduced by heating, composition (X) may be heated and then ejected by the inkjet method and molded. As described above, if the viscosity of composition (X) at 40°C is particularly 16 mPa·s or less, composition (X) can be reduced in viscosity by simply heating it slightly, and this reduced-viscosity composition (X) can be ejected by the inkjet method. The heating temperature of composition (X) is, for example, 20°C or higher and 50°C or lower.

[0084] More specifically, for example, first, a support substrate 2 is prepared. On one surface of this support substrate 2, partition walls 7 are fabricated by photolithography using, for example, a photosensitive resin material. Next, a plurality of light-emitting elements 4 are provided on one surface of the support substrate 2. The light-emitting elements 4 can be fabricated by an appropriate method such as a vapor deposition method or a coating method. 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.

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

[0086] Next, the composition (X) is ejected onto the first passivation layer 61 by, for example, an inkjet method to form a coating film. Applying the inkjet method to both the production of the light-emitting element 4 and the formation of the coating film can particularly improve the production efficiency of the light-emitting device 1. Next, the coating film of the composition (X) is cured by irradiating it with light to produce the encapsulant 5.

[0087] When irradiating the composition (X) with light, the composition (X) may be irradiated with light in an atmosphere containing oxygen, such as an air atmosphere, or may be irradiated with light in an inert atmosphere, such as a nitrogen atmosphere.

[0088] Next, a second passivation layer 62 is provided on the sealing material 5. The second passivation layer 62 can be formed by a vapor deposition method such as a plasma CVD method.

[0089] Next, a photocurable resin material is provided on one surface of the support substrate 2 so as to cover the second passivation layer 62, and then the transparent substrate 3 is placed on top of this resin material. The transparent substrate 3 is, for example, a glass substrate or a transparent resin substrate.

[0090] Next, ultraviolet light is irradiated from the outside toward the transparent substrate 3. The ultraviolet light passes through the transparent substrate 3 and reaches the photocurable resin material, which then hardens, forming the second sealing member 52.

[0091] 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, i.e., bendable, light emitting device 1. Furthermore, 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.

[0092] 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.

[0093] 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 material. Therefore, even if the light emitting device 1 is deformed, for example by bending, damage to the sealing material 5 can be suppressed.

[0094] The light emitting device may include a touch sensor.

[0095] 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 a heterocyclic compound (A1) having a heterocycle containing two or more heteroatoms.

[0096] According to this embodiment, the photocurable resin composition can have good wettability to inorganic materials and good adhesion of the cured product to inorganic materials.

[0097] In the second aspect, in the first aspect, the heterocyclic compound (A1) contains at least one selected from the group consisting of a compound (A11) represented by the following formula (1), a compound (A12) represented by the following formula (2), and a compound (A13) represented by the following formula (3):

[0098]

[0099] In formula (1), X １ is O or a single bond, X ２ is O or CH ２ , X ３ is C=O or CH ２ , X ４ is CH ３ Or H, X ５ is C═O or a single bond, and X １ , X ２ , X ３ and X ５ At least one of them contains O.

[0100]

[0101] In formula (2), Y １ is N or CH, Y ２ is C═O or a single bond.

[0102]

[0103] In formula (3), Z １ is NH, O or S, Z ２ is S, O or a single bond, Z ３ is C═O or a single bond.

[0104] According to this embodiment, the wettability of the photocurable resin composition to inorganic materials is further improved, the viscosity of the photocurable resin composition is reduced, the storage stability of the photocurable resin composition is less likely to decrease, outgassing from the cured product is less likely to occur, and the curability of the photocurable resin composition can be improved.

[0105] In a third aspect, in the first or second aspect, the heterocyclic compound (A1) contains a compound (A11) and a compound (A12).

[0106] According to this embodiment, the wettability and curability of the photocurable resin composition to inorganic materials, as well as the adhesion of the cured product to inorganic materials, can be improved in a well-balanced manner.

[0107] In a fourth aspect, in any one of the first to third aspects, the ratio of the heterocyclic compound (A1) to the photopolymerizable compound (A) is 5% by mass or more and 70% by mass or less.

[0108] In a fifth aspect, in any one of the first to fourth aspects, the photopolymerizable compound (A) further contains a (meth)acrylate (A2) having no heterocycle in the molecule, and the (meth)acrylate (A2) contains a mono(meth)acrylate (A21) having a chain saturated hydrocarbon skeleton having from 6 to 20 carbon atoms in the molecule.

[0109] In a sixth aspect, in the fifth aspect, the ratio of the mono(meth)acrylate (A21) to the (meth)acrylate (A2) is 5% by mass or more and 60% by mass or less.

[0110] According to this embodiment, the flexibility of the cured product can be increased.

[0111] In a seventh aspect, in the fifth or sixth aspect, the ratio of the (meth)acrylate (A2) to the photopolymerizable compound (A) is 20% by mass or more and 80% by mass or less.

[0112] In an eighth aspect, in any one of the first to seventh aspects, the photocurable resin composition further contains a silicone-based surface tension modifier (C).

[0113] According to this embodiment, the wettability of the photocurable resin composition to the inorganic material can be further improved.

[0114] In a ninth aspect, in any one of the first to eighth aspects, the photocurable resin composition has a surface tension at 25° C. of 30 mN / m or less.

[0115] According to this embodiment, the wettability of the photocurable resin composition to the inorganic material can be further improved.

[0116] In a tenth aspect, in any one of the first to ninth aspects, the viscosity of the photocurable resin composition at 25° C. is 40 mPa·s or less.

[0117] According to this embodiment, the photocurable resin composition can have good moldability, and it may be possible to mold it by discharging it by an inkjet method.

[0118] In an eleventh aspect, in any one of the first to tenth aspects, the photocurable resin composition is used in an application in which molding is performed by ejecting the composition by an inkjet method.

[0119] According to this embodiment, the photocurable resin composition can be molded with high positional accuracy.

[0120] In a twelfth aspect, in any one of the first to eleventh aspects, the photocurable resin composition is for producing an optical component.

[0121] According to this embodiment, the optical component can have good adhesion to the inorganic material.

[0122] An optical component according to a thirteenth aspect includes a cured product of the photocurable resin composition according to any one of the first to twelfth aspects.

[0123] According to this embodiment, the optical component can have good adhesion to the inorganic material.

[0124] A method for manufacturing an optical component according to a fourteenth aspect includes ejecting a photocurable resin composition according to any one of the first to twelfth aspects by an inkjet method, and then irradiating the photocurable resin composition with light to cure it.

[0125] According to this embodiment, optical components can be manufactured with high positional accuracy, and the yield is less likely to decrease.

[0126] A light emitting device according to a fifteenth aspect includes a light source and an optical component that transmits light emitted by the light source. The optical component includes a cured product of the photocurable resin composition according to any one of the first to twelfth aspects.

[0127] According to this embodiment, damage to the optical components can be suppressed when the light emitting device is deformed.

[0128] A method for manufacturing a light emitting device according to a sixteenth 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, the method including manufacturing the optical component by the method according to the fourteenth aspect.

[0129] According to this embodiment, optical components can be manufactured with high positional accuracy, and the yield is less likely to decrease.

[0130] Specific examples of the present embodiment will be presented below, but the present disclosure is not limited to the following examples.

[0131] 1. Preparation of Compositions Compositions of the Examples and Comparative Examples were prepared by mixing the components shown in the table below. Details of the components shown in the table are as follows: - Heterocyclic compound #1: 1-vinylimidazole. Manufactured by BASF Japan Ltd. - Heterocyclic compound #2: vinylmethyloxazolidinone. Manufactured by BASF Japan Ltd. Product name: VMOX. - Heterocyclic compound #3: N-hydroxyethylacrylamide. Manufactured by KJ Chemicals Co., Ltd. Product name: ACMO. - Heterocyclic compound #4: 3-acryloyl-2-oxazolidinone. Manufactured by Tokyo Chemical Industry Co., Ltd. - Heterocyclic compound #5: 2-vinyl-1H-benzimidazole. Manufactured by Fujifilm Wako Pure Chemical Industries, Ltd. - Nitrogen-containing compound: N-isopropylacrylamide. Manufactured by KJ Chemicals Co., Ltd. Product name: NIPAM. - (Meth)acrylate #1: Lauryl acrylate. Manufactured by Kyoeisha Chemical Co., Ltd. Product name: Light Acrylate LA. - (Meth)acrylate #2: Isostearyl acrylate. Manufactured by Osaka Organic Chemical Industry Co., Ltd. Product name: ISTA. - (Meth)acrylate #3: Butyl acrylate. Manufactured by Fujifilm Wako Pure Chemical Industries, Ltd. Product name: BA. - (Meth)acrylate #4: Methoxy-polyethylene glycol acrylate. Manufactured by Kyoeisha Chemical Co., Ltd. Product name: Light Acrylate 130A. - (Meth)acrylate #5: 1,10-Decanediol diacrylate. Manufactured by Shin-Nakamura Chemical Co., Ltd. Product name: A-DOD-N. - (Meth)acrylate #6: Pentaerythritol triacrylate. Manufactured by Kyoeisha Chemical Co., Ltd. Product name: PE-3A. - (Meth)acrylate #7: Glycerin triacrylate. Manufactured by Toagosei Co., Ltd. Product Name: M930. - Surface tension adjuster #1: Silicone-based surface tension adjuster. Manufactured by BYK Corporation Product Name: BYK377. - Surface tension adjuster #2: Silicone-based surface tension adjuster. Manufactured by BYK Corporation Product Name: BYK333. - Surface tension adjuster #3: Acrylic-based surface tension adjuster. Manufactured by AGC Seimi Chemical Co., Ltd. Product Name: S651. - Surface tension adjuster #4: Fluorine-based surface tension adjuster. Manufactured by Kyoeisha Chemical Co., Ltd. Product Name: Polyflow No. 77. - Photopolymerization initiator #1: Acylphosphine oxide-based photopolymerization initiator. Manufactured by IGM Resins B.V. Product Name: Omnirad TPO H.Photopolymerization initiator #2: Oxime ester-based photoradical polymerization initiator, manufactured by BASF Japan Ltd. Product name: Irgacure OXE04.

[0132] 2. Evaluation Tests The compositions were subjected to the following evaluation tests, the results of which are shown in the tables below.

[0133] (1) Storage Modulus A composition was applied to form a coating film, and the coating film was irradiated with ultraviolet light at an intensity of 3 W / cm using a Unijet E075IIHD (peak wavelength 395 nm) manufactured by Ushio Inc. under a nitrogen atmosphere. ２ , and the cumulative light amount is 15 J / cm ２ The coating was photocured by irradiating under the conditions of

[0043]

[0044]

[0045]

[0046]

[0047]

[0048]

[0049]

[0050]

[0051]

[0052]

[0053]

[0054]

[0055]

[0056]

[0057]

[0058]

[0059]

[0060]

[0061]

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098] [009 ...100]

[0099]

[0099]

[0100]

[0099]

[0099]

[0099]

[0100]

[0099]

[0099]

[0099]

[0101] [009

[0134] (2) Viscosity at 25°C and 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 number DHR-2) at a shear rate of 1000 s －１ The measurement was carried out under the following conditions.

[0135] (3) Surface Tension The surface tension of the composition was measured using a contact angle meter (manufactured by Kyowa Interface Science Co., Ltd., Model PCA-1) under the condition of a droplet volume of 4 μL.

[0136] (4) Wettability Each composition was placed in a cartridge of an inkjet printer (manufactured by Fujifilm Corporation, product name: Material Printer MP2831), and it was confirmed that the composition in the cartridge could be ejected from the nozzle of the inkjet printer.

[0137] Subsequently, droplets of the composition were ejected from a nozzle onto the SiN film at 600 dpi to prepare coating films having a thickness of 10 μm, 15 μm, and 20 μm.

[0138] The coating film was observed 3 minutes after it was prepared.

[0139] When the surfaces of the 10 μm thick coating film, the 15 μm thick coating film, and the 20 μm thick coating film were all flat, the coating film was evaluated as "A."

[0140] The surface of the 10 μm thick coating film was uneven or wavy and not flat, but the surfaces of the 15 μm thick coating film and the 20 μm thick coating film were both flat, and the coating was evaluated as "B."

[0141] The surfaces of the 10 μm thick coating film and the 15 μm thick coating film were uneven or wavy and not flat, but the surface of the 20 μm thick coating film was flat, and was evaluated as "C."

[0142] When the surfaces of the 10 μm thick coating film, the 15 μm thick coating film, and the 20 μm thick coating film were uneven or wavy and not flat, the coating film was evaluated as "D."

[0143] (5) Inkjet Properties The composition was placed in the cartridge of an inkjet printer (manufactured by Fujifilm Corporation, product name: Material Printer MP2831), and droplets of the composition were ejected from the nozzle of the inkjet printer under conditions of a temperature of 40°C and a frequency of 1 kHz. The droplets were observed with a high-speed camera. The results were evaluated as follows: "A" if the droplets did not separate; "B" if the satellites separated from the original droplets and then merged with the original droplets to form a single droplet again; and "C" if the satellites separated from the original droplets and did not merge.

[0144] (6) Curability The composition was measured using an infrared spectrometer (Agilent Technologies, Model No. Agilent Cary 610 FTIR Microscope System) to obtain an IR spectrum.

[0145] The composition was applied to form a coating film having a thickness of 10 μm, and the coating film was irradiated with light having a peak wavelength of 395 nm at an irradiation intensity of 0.5 W / cm using a UV irradiator (manufactured by Ushio Inc., model number Unijet E075IIHD) under a nitrogen atmosphere. ２ And the cumulative light intensity is 1.5 J / cm ２ Subsequently, the composition (cured product) after irradiation with ultraviolet light was measured using the above-mentioned infrared spectrometer to obtain an IR spectrum.

[0146] In each of the two IR spectra, －１ The peak intensity of the absorption of the acryloyl group appearing in the coating film was measured. ０ and the peak intensity I for the cured product １ From this, {1-(I ０ -I １ ) / I ０ The reduction rate of the reactive functional groups in the composition before and after irradiation with ultraviolet light was calculated using the formula: × 100 (%). The result was taken as the reaction rate, and the reaction rate was evaluated as "A" when it was 90% or more, "B" when it was 80% or more but less than 90%, and "C" when it was less than 80%.

[0147] (7) Outgassing Evaluation The outgassing when the cured composition was heated was sampled by the headspace method and measured by gas chromatography. Specifically, 100 mg of the composition was placed in a 22 mL headspace vial. Next, the composition was irradiated with light of a peak wavelength of 395 nm at an irradiation intensity of 0.5 W / cm using a UV irradiator (manufactured by Ushio Inc., model number Unijet E075IIHD) under a nitrogen atmosphere. ２ And the cumulative light intensity is 1.5 J / cm ２ The composition was cured by irradiating under the conditions of

[0043] , and then the vial was sealed. The composition was then heated at 110°C for 30 minutes, and the gas phase in the vial was introduced into a gas chromatograph for analysis. The concentration of outgassing from the composition was determined based on the peak area of ​​the resulting gas chromatogram. The outgassing concentration is the volume fraction of outgassing in the gas phase of the vial relative to the volume of the vial (22 mL).

[0148] The outgas concentrations were determined using toluene as a reference substance. Specifically, two reference samples with toluene concentrations of 1000 ppm and 100 ppm were prepared by volatilizing toluene in a vial. Each reference sample was introduced into a gas chromatograph and analyzed. The relationship between peak area and concentration was determined from the peak areas of the two chromatograms obtained, and the outgas concentrations were determined based on these results.

[0149] As a result, the outgas concentration was evaluated as "A" when it was 50 ppm or less, "B" when it was more than 50 ppm and less than 100 ppm, and "C" when it was more than 100 ppm.

[0150] (8) Adhesion A silicon oxynitride (SiON) film, an inorganic material, was formed on a glass slide by CVD to a thickness of 1 μm. The composition was applied to the inorganic material to a thickness of 10 μm to form a coating film. The coating film was then irradiated with light having a peak wavelength of 395 nm at an irradiation intensity of 0.5 W / cm using a UV irradiator (manufactured by Ushio Inc., model number Unijet E075IIHD) under a nitrogen atmosphere. ２ And the cumulative light intensity is 1.5 J / cm ２ The coating film was pulled in a 90-degree direction using an autograph (manufactured by Shimadzu Corporation, model number AGS-X) to measure the peel strength.

[0151] As a result, peel strength of 100 mN / cm or more was evaluated as "A", peel strength of 40 mN / cm or more but less than 100 mN / cm was evaluated as "B", and peel strength of less than 40 mN / cm was evaluated as "C".

[0152] (9) Device Evaluation A glass substrate with an ITO electrode was prepared. The glass substrate with an ITO electrode had a planar size of 30 mm x 30 mm, the ITO electrode had a thickness of 150 nm, and the entire thickness of the glass substrate with an ITO electrode was 700 μm.

[0153] The glass substrate with the ITO electrode was washed with acetone and then with isopropanol.

[0154] Next, a hole injection layer, a hole transport layer, a light-emitting layer, an electron injection layer, and a cathode were sequentially formed on the anode by vacuum deposition using the 150 nm-thick ITO electrode on the glass substrate with the ITO electrode, thereby producing an organic EL device having a structure of anode / hole injection layer / hole transport layer / light-emitting layer / electron injection layer / cathode and measuring 2 mm × 2 mm in plan view.

[0155] The hole injection layer was made from 4,4′,4″-tris{2-naphthyl(phenyl)amino}triphenylamine (2-TNATA).

[0156] The hole transport layer was made from N,N'-diphenyl-N,N'-dinaphthylbenzidine (α-NPD).

[0157] The light-emitting layer was made of tris(8-hydroxyquinolinato)aluminum, a metal complex material, and had a thickness of 100 μm. This light-emitting layer also functions as an electron transport layer.

[0158] The electron injection layer was made from lithium fluoride.

[0159] The cathode was made of aluminum and had a thickness of 150 nm.

[0160] In this way, an organic EL element was fabricated on the glass substrate.

[0161] Next, a mask (cover) having openings measuring 10 mm × 10 mm in plan view was placed on the glass substrate so that the organic EL elements were exposed through the openings. In this state, a SiN film (first passivation layer) also measuring 10 mm × 10 mm in plan view was formed by plasma CVD so as to cover the organic EL elements.

[0162] Subsequently, the composition was ejected onto the first passivation layer using an inkjet device under a nitrogen atmosphere to form a coating film having a thickness of 10 μm. This coating film was irradiated with light having a peak wavelength of 395 nm using a UV irradiator (manufactured by Ushio Inc., model number Unijet E075IIHD) at an irradiation intensity of 0.5 W / cm. ２ And the cumulative light intensity is 1.5 J / cm ２ The coating was cured to prepare a sealing material.

[0163] Next, a mask (cover) with a 10 mm × 10 mm opening was placed so that the sealing material was exposed through the opening, and in this state, a SiN film (second passivation layer) with a thickness of approximately 1 μm was formed on the sealing material by plasma CVD.

[0164] The second passivation layer was attached to an alkali-free glass sheet (manufactured by Corning, product name Eagle XG) measuring 30 mm × 30 mm × 0.7 mm using a transparent, substrate-less double-sided tape measuring 30 mm × 30 mm × 25 μm, thereby producing an organic EL light-emitting device.

[0165] Immediately after fabrication, the organic EL light-emitting device was exposed to an atmosphere at a temperature of 85°C and a relative humidity of 85% by mass for 70 hours, and then a voltage of 6 V was applied to the organic EL light-emitting device to cause it to emit light. The light-emitting state of the organic EL element was observed visually and microscopically to confirm the presence or absence of dark spots, and if dark spots were observed, their diameters were measured. As a result, the organic EL light-emitting device was evaluated as "C" if the maximum diameter of the dark spots was more than 50 μm and not more than 300 μm, "B" if the maximum diameter of the dark spots was 50 μm or less, and "A" if no dark spots were observed.

[0166] The diameter of the dark spot can be regarded as an index for evaluating the degree of penetration of the sealing material into the pinholes in the passivation layer and the degree to which moisture in the sealing material is discharged as outgassing.

[0167] (10) Flexibility A silicon oxynitride (SiON) film, an inorganic material, was formed on a polyimide film substrate by a CVD method to a thickness of 1 μm. The composition was applied to the inorganic material to a thickness of 10 μm to form a coating film, and this coating film was irradiated with light having a peak wavelength of 395 nm at an irradiation intensity of 0.5 W / cm using a UV irradiator (manufactured by Ushio Inc., Model No. Unijet E075IIHD) under a nitrogen atmosphere. ２ And the cumulative light intensity is 1.5 J / cm ２ A film having a thickness of 10 μm was produced by irradiating under the conditions of

[0043] In this way, an evaluation sample including a substrate, an inorganic film, and a film was produced.

[0168] 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.

[0169] As a result, the evaluation sample was rated as "A" if no peeling or cracking was observed in its appearance after 100,000 tests at a curvature radius of 1.5 mm, as "B" if no abnormalities were observed at a curvature radius of 2.0 mm but abnormalities were observed at a curvature radius of 1.5 mm, as "C" if no abnormalities were observed at a curvature radius of 3.0 mm but abnormalities were observed at a curvature radius of 2.0 mm, and as "D" if abnormalities were observed at a curvature radius of 3.0 mm.

[0170]

[0171]

[0172]

[0173] 1 Light emitting device 4 Light emitting element (light source) 5 Sealant (optical component)

Claims

1. A photocurable resin composition containing a photopolymerizable compound (A) and a photoinitiator (B), wherein the photopolymerizable compound (A) contains a heterocyclic compound (A1) having a heterocycle containing two or more heteroatoms.

2. The complex cyclic compound (A1) contains at least one selected from the group consisting of a compound (A11) represented by the following formula (1), a compound (A12) represented by the following formula (2), and a compound (A13) represented by the following formula (3). In formula (1), X １ is O or a single bond, X ２ is O or CH ２ , X ３ is C=O or CH ２ , X ４ is CH ３ or H, X ５ is C=O or a single bond, and at least one of X １ , X ２ , and X ３ contains O. In formula (2), Y １ is N or CH, Y ２ is C=O or a single bond. In formula (3), Z １ is NH, O, or S, Z ２ is S, O, or a single bond, Z ３ is C=O or a single bond. The photocurable resin composition according to claim 1.

3. The photocurable resin composition according to claim 2, wherein the heterocyclic compound (A1) contains the compound (A11) and the compound (A12).

4. The photocurable resin composition according to claim 1, wherein the ratio of the heterocyclic compound (A1) to the photopolymerizable compound (A) is 5% by mass or more and 70% by mass or less.

5. The photocurable resin composition according to claim 1, wherein the photopolymerizable compound (A) further contains a (meth)acrylate (A2) having no heterocycle in the molecule, and the (meth)acrylate (A2) contains a mono(meth)acrylate (A21) having a linear saturated hydrocarbon skeleton having 6 to 20 carbon atoms in the molecule.

6. The photocurable resin composition according to claim 5, wherein the ratio of the mono(meth)acrylate (A21) to the (meth)acrylate (A2) is 5% by mass or more and 60% by mass or less.

7. The photocurable resin composition according to claim 5 or 6, wherein the ratio of the (meth)acrylate (A2) to the photopolymerizable compound (A) is 20% by mass or more and 80% by mass or less.

8. The photocurable resin composition according to claim 1, further containing a silicone-based surface tension modifier (C).

9. The photocurable resin composition according to claim 1, having a surface tension at 25°C of 30 mN / m or less.

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

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

12. The photocurable resin composition according to claim 1, which is for producing optical parts.

13. An optical part including a cured product of the photocurable resin composition according to claim 1.

14. A method for manufacturing an optical part, including ejecting the photocurable resin composition according to claim 1 by an inkjet method and then irradiating the photocurable resin composition with light for curing.

15. A light-emitting device including a light source and an optical part that transmits light emitted by the light source, wherein the optical part includes a cured product of the photocurable resin composition according to claim 1.

16. A method of manufacturing a light-emitting device including a light source and an optical component that transmits light emitted by the light source, the method including manufacturing the optical component by the method according to claim 14.

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