Curable composition, cured product, optical component, and method for producing a cured product

Abstract

To provide a curable composition that yields a cured product with superior transparency for 400 nm-760 nm light, a high refractive index, and superior solvent resistance.SOLUTION: A curable composition includes (A) a compound with three or more thiol groups in each molecule, (B) a compound with two or more carbon-carbon unsaturated bonds in each molecule, and (C) a photoradical generator.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a curable composition, a cured product, an optical component, and a method for producing a cured product. [Background technology]

[0002] In recent years, with the rapid development of digital cameras and camera-equipped mobile phones, there has been a demand for miniaturization and higher pixel counts in solid-state image sensors. Transparent resin materials, which offer superior moldability, lightness, and impact resistance compared to inorganic glass, are being used in a variety of applications. For example, transparent resin materials are used as materials for planarization films and microlenses in image display elements and optical elements. Transparent resin materials used in these applications require properties such as good transparency, solvent resistance, and high refractive index.

[0003] As resin materials, sulfur-containing polymers obtained by bulk polymerization of dithiol compounds and polyfunctional alkenyl compounds such as tetravinylsilane have been proposed (see, for example, Patent Document 1).

[0004] Furthermore, as resin materials that are expected to have a high refractive index and improved solvent resistance, resin materials and cured products formed from trithiol compounds with many crosslinking points, polyfunctional alkenyl compounds such as tetravinylsilane, and thermal radical generators have been proposed (see, for example, Patent Document 2). [Prior art documents] [Patent Documents]

[0005] [Patent Document 1] U.S. Patent Publication No. 8975356 [Patent Document 2] Japanese Patent Publication No. 2015-25092 [Overview of the project] [Problems that the invention aims to solve]

[0006] However, the conventionally proposed resin materials mentioned above have the following drawbacks. The resin material disclosed in Patent Document 1 has the problem of low solvent resistance. Furthermore, the resin material disclosed in Patent Document 2 has the problem of a low refractive index because the crosslinking reaction does not proceed sufficiently due to the low curing temperature. In other words, conventionally proposed resin materials have room for improvement in terms of refractive index and solvent resistance.

[0007] Therefore, the present invention aims to provide a curable composition that has good transparency to light in the 400 nm to 760 nm range, a high refractive index, and excellent solvent resistance, as well as a cured product obtained therefrom, an optical component, and a method for producing the cured product. [Means for solving the problem]

[0008] The inventors of this invention conducted diligent research to solve the problems of the prior art described above, and as a result, discovered that the above problems can be solved by the following means, and thus completed the present invention. In other words, the present invention is as follows.

[0009] [1] (A) A compound having three or more thiol groups in the molecule, (B) Compounds having two or more carbon-carbon unsaturated bonds in the molecule, (C) Photoradical generator and, A curable composition containing the following. [2] The curable composition according to [1], wherein the compound (A) is an aromatic thiol having three or more thiol groups in its molecule. [3] The aforementioned compound (B) The curable composition according to [1] or [2] above, which is a compound having a structure in which one or more atoms selected from the group consisting of silicon atoms, germanium atoms, and tin atoms are directly bonded to one or more groups selected from the group consisting of vinyl groups, vinyl ether groups, allyl groups, allyl ether groups, and norbornyl groups. [4] The compound (B) is a curable composition according to any one of [1] to [3] above, containing at least one selected from the group consisting of tetravinylsilane, phenyltrivinylsilane, methyltrivinylsilane, hexavinyl disilane, tetravinylgermane, phenyltrivinylgermane, methyltrivinylgermane, and hexavinyl digermane. [5] The photo radical generator (C) is a curable composition according to any one of [1] to [4] above, which is a compound having an absorption maximum in the wavelength range of 300 nm or more and 400 nm or less, and having a value of the gram absorption coefficient at a wavelength of 365 nm of 0.2 L / (g·cm) or less. [6] a cured product of the curable composition according to any one of [1] to [5] above, a cured product having a value of b / a of 0.3 or less, where b (Abs.) is the absorbance with respect to light having a wavelength of 426 nm and a (mm) is the measurement optical path length of the absorbance. [7] The cured product according to [6] above, having a refractive index with respect to light having a wavelength of 532 nm of 1.75 or more under the temperature condition of 25°C. [8] An optical member containing the cured product according to [6] or [7] above. [9] (A) A compound having three or more thiol groups in the molecule, (B) A compound having two or more carbon-carbon unsaturated bonds in the molecule, (C) A photo radical generator, A method for producing a cured product, comprising irradiating the curable composition containing with light in the wavelength range of 310 nm or more and 390 nm or less so that the integrated light amount becomes 70 J / cm 2 or less to cure it.

[10] A method for producing a cured product according to [9] above, comprising a step of curing the curable composition using a light emitting diode light source having an emission peak wavelength of 350 to 380 nm.

[11] The photo radical generator (C) is a compound having an absorption maximum in the range of 300 nm or more and 400 nm or less in wavelength, and having a value of the gram absorption coefficient at a wavelength of 365 nm of 0.2 L / (g·cm) or less The method for producing a cured product according to the above [9] or

[10] .

Advantages of the Invention

[0010] According to the present invention, there can be provided a curable composition capable of obtaining a cured product having good transparency to light of 400 nm to 760 nm, a high refractive index, and excellent solvent resistance, a cured product obtained therefrom, an optical member, and a method for producing a cured product.

Embodiments for Carrying Out the Invention

[0011] Hereinafter, embodiments for carrying out the present invention (hereinafter, also referred to as "the present embodiment") will be described in detail. It should be noted that the following present embodiment is an exemplification for explaining the present invention, and is not intended to limit the present invention to the following contents. The present invention can be variously modified and implemented within the scope of its gist.

[0012] 〔Curable Composition〕 The curable composition of the present embodiment contains (A) a compound having three or more thiol groups in the molecule (hereinafter, may be referred to as compound (A)), (B) a compound having two or more carbon-carbon unsaturated bonds in the molecule, (C) a photo radical generator, and

[0013] With the above configuration, a curable composition capable of obtaining a cured product having good transparency to light of 400 nm to 760 nm, a high refractive index, and excellent solvent resistance can be provided.

[0014] (Compound (A)) The curable composition of the present embodiment contains (A) a compound having three or more thiol groups in the molecule (hereinafter, may be referred to as compound (A) in some cases). (A) The thiol groups in a compound having three or more thiol groups in its molecule include unsubstituted thiol groups (i.e., -SH groups) and substituted thiol groups (for example, those listed below).

[0015] A substituted thiol group is a group in which the hydrogen atoms of an unsubstituted thiol group are replaced by other groups, such as substituted or unsubstituted alkyl groups. As substituted thiol groups, substituted or unsubstituted alkylthio groups include methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, i-butylthio, sec-butylthio, t-butylthio, n-pentylthio, iso-pentylthio, n-hexylthio, iso-hexylthio, 2-ethylhexylthio, 3,5,5-trimethylhexylthio, n-heptylthio, n-octylthio, n-nonylthio, and other linear or branched alkylthio groups with a total of 1 to 10 carbon atoms, cyclopentylthio, and cyclopentylthio. Cycloalkylthio groups with a total of 5 to 10 carbon atoms, such as chlorohexylthio groups, methoxyethylthio groups, ethoxyethylthio groups, n-propoxyethylthio groups, iso-propoxyethylthio groups, n-butoxyethylthio groups, iso-butoxyethylthio groups, tert-butoxyethylthio groups, n-pentyloxyethylthio groups, iso-pentyloxyethylthio groups, n-hexyloxyethylthio groups, iso-hexyloxyethylthio groups, n-heptyloxyethylthio groups, and other alkoxyalkylthio groups with a total of 2 to 10 carbon atoms, and benzylthio groups. Alkylthioalkylthio groups with a total of 2 to 10 carbon atoms, such as aralkylthio groups, methylthioethylthio groups, ethylthioethylthio groups, n-propylthioethylthio groups, iso-propylthioethylthio groups, n-butylthioethylthio groups, iso-butylthioethylthio groups, tert-butylthioethylthio groups, n-pentylthioethylthio groups, iso-pentylthioethylthio groups, n-hexylthioethylthio groups, iso-hexylthioethylthio groups, n-heptylthioethylthio groups, etc., and substituted or unsubstituted arylthio groups such as phenylthio groups, na Phthylthio group, 2-methylphenylthio group, 3-methylphenylthio group, 4-methylphenylthio group, 2-ethylphenylthio group, propylphenylthio group, butylphenylthio group, hexylphenylthio group, cyclohexylphenylthio group, 2,4-dimethylphenylthio group, 2,5-dimethylphenylthio group, 2,6-dimethylphenylthio group, 3,4-dimethylphenylthio group, 3,5-dimethylphenylthio group, 3,6-dimethylphenylthio group, 2,3,4-trimethylphenylthio group, 2,3,5-trimethylphenylthio group, 2,3,Monoalkoxyarylthio groups with a total of 12 or fewer carbon atoms substituted with substituted or unsubstituted alkyloxy groups with a total of 12 or fewer carbon atoms, such as 6-trimethylphenylthio group, 2,4,5-trimethylphenylthio group, 2,4,6-trimethylphenylthio group, 3,4,5-trimethylphenylthio group, etc., 2-methoxyphenylthio group, 3-methoxyphenylthio group, 4-methoxyphenylthio group, 2-ethoxyphenylthio group, propoxyphenylthio group, butoxyphenylthio group, hexyloxyphenylthio group, cyclohexyloxyphenylthio group, etc., monoalkoxyarylthio groups with a total of 12 or fewer carbon atoms substituted with substituted or unsubstituted alkyloxy groups with a total of 12 or fewer carbon atoms, such as 2-methoxyphenylthio group, 3-methoxyphenylthio group, 4-methoxyphenylthio group, 2-ethoxyphenylthio group, propoxyphenylthio group, butoxyphenylthio group, hexyloxyphenylthio group, cyclohexyloxyphenylthio group, etc., 2,3-dimethoxyphenylthio group, 2,4-dimethoxyphenylthio group, 2,5-dimethoxyphenylthio group, 2,6-dimethoxyphenylthio group, 3,4-dimethoxyphenylthio group, 3,5-dimethoxyphenylthio Examples include dialkoxyarylthio groups with a total of 12 or fewer carbon atoms substituted with alkyloxy groups having 6 or fewer carbon atoms, such as 3,6-dimethoxyphenylthio group, 4,5-dimethoxy-1-naphthylthio group, 4,7-dimethoxy-1-naphthylthio group, 4,8-dimethoxy-1-naphthylthio group, 5,8-dimethoxy-1-naphthylthio group, and 5,8-dimethoxy-2-naphthylthio group; and arylthio groups with a total of 12 or fewer carbon atoms substituted with halogen atoms, such as chlorophenylthio group, dichlorophenylthio group, trichlorophenylthio group, bromophenylthio group, dibromophenylthio group, iodophenylthio group, fluorophenylthio group, chloronaphthylthio group, bromonaphthylthio group, difluorophenylthio group, trifluorophenylthio group, tetrafluorophenylthio group, and pentafluorophenylthio group. From the viewpoint of heat resistance, preferred substituted or unsubstituted alkylthio groups include linear or branched alkylthio groups with a total of 1 to 10 carbon atoms or less, such as methylthio group, ethylthio group, n-propylthio group, i-propylthio group, n-butylthio group, i-butylthio group, sec-butylthio group, t-butylthio group, n-pentylthio group, iso-pentylthio group, n-hexylthio group, iso-hexylthio group, 2-ethylhexylthio group, 3,5,5-trimethylhexylthio group, n-heptylthio group, n-octylthio group, and n-nonylthio group. From the viewpoint of refractive index, methylthio group, ethylthio group, n-propylthio group, and i-propylthio group are even more preferred.

[0016] Compound (A) is preferably an aromatic thiol from the viewpoint of improving the refractive index properties of the cured product by high crosslinking density. Aromatic thiols are compounds that have a structure in which at least one thiol group is directly bonded to an aromatic ring. Compound (A) may have two or more thiol groups directly bonded to one aromatic ring, or one or more thiol groups directly bonded to each of the two or more aromatic rings present in one molecule, and the aromatic ring may contain a heteroatom. Aromatic thiols include, but are not limited to, 1,3,5-benzenetrithiol, 1,2,3-benzenetrithiol, 1,2,4-benzenetrithiol, trithiocyanuric acid, 1,2,3,4-benzenetetrathiol, 1,2,4,5-benzenetetrathiol, 1,2,3,5-benzenetetrathiol, 1,2,3,4,5,6-benzenehexathiol, and other benzene polythiols, 1,3,6-naphthalenetrithiol, 1 Examples include naphthalene polythiols such as 2,4,5-naphthalenetetrathiol, 1,4,5,8-naphthalenetetrathiol, 2,3,6,7-naphthalenetetrathiol, 1,2,3,4,6,7-naphthalenehexathiol, and 1,2,3,5,6,7-naphthalenehexathiol, as well as polycyclic aromatic polythiols such as 1,4,5-anthracenatethiol, 1,4,5,8-anthracenatetetrathiol, and 1,2,6,7-pyrenetetrathiol. Compound (A) may be one of the above compounds used alone, or two or more compounds may be used in combination.

[0017] (Compound (B)) The curable composition of this embodiment contains (B) a compound having two or more carbon-carbon unsaturated bonds in its molecule (hereinafter sometimes referred to as compound (B)). (B) The carbon-carbon unsaturated bonds in a compound having two or more carbon-carbon unsaturated bonds in its molecule include both reactive carbon-carbon double bonds and carbon-carbon triple bonds. However, delocalized bonds such as those in aromatic rings are not included in the definition of carbon-carbon unsaturated bonds. Compound (B) can have the above-mentioned carbon-carbon unsaturated bond in the compound by having a carbon-carbon unsaturated bond-containing group. The carbon-carbon unsaturated bond-containing groups are not limited to the following, but examples include norbornyl group, vinylsilyl group, vinylgermyl group, vinylstannyl group, vinylprumville group, allyl ether group, allyl group, vinyl ether group, fumarate group, propenyl group, maleimide group, methacrylic group, acrylic group, crotonate group, styryl group, and butadiene group. In particular, from the viewpoint of good reactivity with the thiol group of compound (A) described above, norbornyl group, vinylsilyl group, vinylgermyl group, vinylstannyl group, allyl ether group, allyl group, vinyl ether group, fumarate group, propenyl group, and maleimide group are preferred, and furthermore, from the viewpoint of heat resistance of the curable composition and cured product of this embodiment, vinylsilyl group, vinylgermyl group, vinylstannyl group, allyl ether group, allyl group, norbornyl group, and vinyl ether group are more preferred.

[0018] In the curable composition of this embodiment, it is preferable that compound (B) does not contain a C=N bond. This reduces the amount of heteroatom bonds formed after the reaction, resulting in high heat resistance.

[0019] Compound (B) is preferably a compound having a structure in which one or more atoms selected from the group consisting of silicon atoms, germanium atoms, and tin atoms are directly bonded to one or more groups selected from the group consisting of vinyl groups, vinyl ether groups, allyl groups, allyl ether groups, and norbornyl groups. This increases the density of the cured material, resulting in an improvement in the refractive index of the cured material.

[0020] Compound (B) is not limited to the following, but examples include vinylsilane compounds such as tetravinylsilane, phenyltrivinylsilane, methyltrivinylsilane, dimethyldivinylsilane, and diphenyldivinylsilane; vinylgermane compounds such as tetravinylgermane, phenyltrivinylgermane, methyltrivinylgermane, and dimethyldivinylgermane; vinylstannane compounds such as tetravinylstannane; vinylpolysilane compounds such as hexavinyldisilane; vinylpolygermane compounds such as hexavinyldigermane; vinylsiloxanes such as 2,4,6,8-tetramethyl-2,4,6,8-tetravinylcyclotetrasiloxane; and substituted isocyanurates such as triallyl isocyanurate and triallyl cyanurate. Compound (B) may be one of the above compounds used alone, or two or more compounds may be used in combination.

[0021] (Mixing ratio of compound (A) and compound (B)) In the curable composition of this embodiment, the combination of compound (A) and compound (B) described above makes it possible to achieve a high refractive index, colorless transparency, and solvent resistance. Regarding the mixing ratio of compound (A) and compound (B) in the curable composition, the molar ratio of thiol groups in compound (A) to carbon-carbon unsaturated bonds in compound (B), namely [thiol groups in compound (A) (mol)] / [carbon-carbon unsaturated bonds in compound (B) (mol)], is preferably 0.5 to 2.0 from the viewpoint of obtaining a high reaction rate and a high refractive index of the cured product. Furthermore, from the viewpoint of obtaining excellent weather resistance, the molar ratio is more preferably 1.1 or higher, and from the viewpoint of further improving the hardness of the cured product, the molar ratio is more preferably 1.8 or lower. It is preferable to adjust the mixing ratio of compound (A) and compound (B) in the curable composition so that the above molar ratio is achieved.

[0022] (Photoradical Generator (C)) The curable composition of this embodiment contains a photoradical generator (C). The carbon-carbon unsaturated bond site of compound (B) described above and the thiol group of compound (A) described above undergo a radical growth-chain transfer reaction. That is, radicals present in the system abstract hydrogen from the thiol group, and the thiol group from which hydrogen has been abstracted becomes a radical and reacts with the carbon-carbon unsaturated bond site, resulting in radical transfer and molecular chain growth, and the polymerization continues. Generally, radical growth-chain transfer reactions proceed spontaneously in response to heat and ultraviolet light, even without a catalyst, but the curable composition of this embodiment contains a photoradical generator (C), which facilitates reaction control in the curing reaction, improves crosslinking density, and improves the refractive index, mechanical properties, and heat resistance of the cured product. Therefore, the photoradical generator (C) is used.

[0023] The photoradical generator (C) is not particularly limited as long as it generates radicals in response to light, but a photoradical generator that absorbs light at a wavelength of 365 nm is preferred, and more specifically, the following group of compounds (1) to (12) that absorb light at a wavelength of 365 nm are preferred.

[0024] (1): Benzophenone derivatives; for example, benzophenone, 4,4'-bis(diethylamino)benzophenone, o-methyl benzoylbenzoate, 4-benzoyl-4'-methyldiphenyl ketone, dibenzyl ketone, fluorenone, etc.

[0025] (2): Acetophenone derivatives; for example, trichloroacetophenone, 2,2'-diethoxyacetophenone, 2-hydroxy-2-methylpropiophenone, 2,2-dimethoxy-1,2-diphenylethane-1-one, 1-hydroxycyclohexylphenyl ketone, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one, 2-hydroxy-1-{4-[4-(2-hydroxy-2-methylpropionyl)-benzyl]-phenyl}-2-methylpropan-1-one, methyl phenylglyoxylate, (2-hydroxy-1-{4-[4-(2-hydroxy-2-methylpropionyl)-benzyl]-phenyl}-2-methylpropan-1-one) (Irgacure® 127 manufactured by BASF Ltd).

[0026] (3): Thioxanthone derivatives; for example, thioxanthone, 2-methylthioxanthone, 2-isopropylthioxanthone, diethylthioxanthone, etc.

[0027] (4): Benzyl derivatives; for example, benzyl, benzyldimethyl ketal, benzyl-β-methoxyethyl acetal, etc.

[0028] (5) Benzoin derivatives; for example, benzoin, benzoin methyl ether, 2-hydroxy-2-methyl-1-phenylpropan-1-one, etc.

[0029] (6): Oxime compounds; for example, 1-phenyl-1,2-butanedione-2-(O-methoxycarbonyl)oxime, 1-phenyl-1,2-propanedione-2-(O-methoxycarbonyl)oxime, 1-phenyl-1,2-propanedione-2-(O-ethoxycarbonyl)oxime, 1-phenyl-1,2-propanedione-2-(O-benzoyl)oxime, 1,3-diphenylpropanetrione-2-(O-ethoxycarbonyl)oxime, 1 Examples include -phenyl-3-ethoxypropanetrione-2-(O-benzoyl)oxime, 1,2-octanedione, 1-[4-(phenylthio)-2-(O-benzoyloxime)] (Irgacure® OXE-01, manufactured by BASF Ltd.), ethanone-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]-1-(O-acetyloxime) (Irgacure® OXE02, manufactured by BASF Ltd.), etc.

[0030] (7): α-hydroxyketone compounds; for example, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1-[4-(2-hydroxyethoxy)phenyl]-2-hydroxy-2-methyl-1-propan-1-one, 2-hydroxy-1-{4-[4-(2-hydroxy-2-methylpropionyl)-benzyl]phenyl}-2-methylpropane, etc.

[0031] (8): α-aminoalkylphenone compounds; for example, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butanone-1 (Irgacure® 369 manufactured by BASF Ltd.), 2-dimethylamino-2-(4-methylbenzyl)-1-(4-morpholin-4-ylphenyl)butan-1-one, etc.

[0032] (9): Phosphine oxide compounds; for example, bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide, bis(2,6-dimethoxybenzoyl)-2,4,4-trimethyl-pentylphosphine oxide, 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide (Darocure® TPO, manufactured by BASF Ltd).

[0033] (10): Titanocene compounds; for example, bis(η5-2,4-cyclopentadiene-1-yl)bis(2,6-difluoro-3-(1H-pyrrole-1-yl)phenyl)titanium.

[0034] (11): Benzoate derivatives; for example, ethyl-p-(N,N-dimethylaminobenzoate).

[0035] (12): Acridine derivatives; for example, 9-phenylacridine.

[0036] The photoradical generator (C) described above may be used alone or in combination of two or more types.

[0037] The photoradical generator (C) is preferably a compound that has an absorption maximum in the wavelength range of 300 nm to 400 nm and has a Gram extinction coefficient of 1.0 L / (g·cm) or less for light at a wavelength of 365 nm, more preferably 0.2 L / (g·cm) or less, and even more preferably 0.1 L / (g·cm) or less, from the viewpoint of increasing the transmittance of light with wavelengths of 400 nm to 420 nm and suppressing discoloration. The Gram extinction coefficient for absorption at a wavelength of 365 nm can be measured by preparing an acetonitrile solution of the photoradical generator (C) and using a transmittance measuring device (for example, Hitachi High-Technologies Corporation's U-4100 spectrophotometer). As the photoradical generator (C) that satisfies the above conditions, for example, α-hydroxyacetophenones are preferred, and 2-hydroxy-2-methylpropiophenone is more preferred.

[0038] The maximum absorption wavelength of the photoradical generator (C) in the wavelength range of 300 nm to 400 nm is preferably 360 nm or less, more preferably 350 nm or less, and even more preferably 340 nm or less, from the viewpoint of further increasing the transmittance of light rays with wavelengths of 400 nm to 420 nm and further suppressing discoloration.

[0039] The content of the photoradical generator (C) in the curable composition of this embodiment is preferably 0.1 parts by mass to 10 parts by mass, more preferably 0.2 parts by mass to 5 parts by mass, and even more preferably 0.5 parts by mass to 3 parts by mass, based on 100 parts by mass of the total mass of compound (A) and compound (B) described above. A content of 0.1 parts by mass or more is preferable because curing proceeds well, and a content of 10 parts by mass or less is preferable because there is less discoloration of the cured product after curing by light or heat.

[0040] (Thermal radical generator) The curable composition of this embodiment may contain a thermal radical generator. The thermal radical generator is not particularly limited as long as it generates radicals when heated. Examples of thermal radical generators include, but are not limited to, organic peroxides such as benzoyl peroxide, lauryl peroxide, t-butyl peroxide, and cumene hydroperoxide; and azo compounds such as azobisisobutyronitrile.

[0041] The thermal radical generators specifically include azonitrile compounds such as 2,2'-azobis(4-methoxy-2,4-dimethylvaleronitrile) (V-70, manufactured by Wako Pure Chemical Industries), 2,2'-azobis(2,4-dimethylvaleronitrile) (V-65, manufactured by Wako Pure Chemical Industries), 2,2'-azobisisobutyronitrile (V-60, manufactured by Wako Pure Chemical Industries), and 2,2'-azobis(2-methylbutyronitrile) (V-59, manufactured by Wako Pure Chemical Industries); octanoyl peroxide (Perloyl® O, manufactured by NOF Corporation), lauroyl peroxide (Perloyl Perloyl (registered trademark) L, manufactured by NOF Corporation, Stearoyl peroxide (Perloyl (registered trademark) S, manufactured by NOF Corporation), Succinic acid peroxide (Perloyl (registered trademark) SA, manufactured by NOF Corporation), Benzoyl peroxide (Nipper (registered trademark) BW, manufactured by NOF Corporation), Isobutyryl peroxide (Perloyl (registered trademark) IB, manufactured by NOF Corporation), 2,4-Dichlorobenzoyl peroxide (Nipper (registered trademark) CS, manufactured by NOF Corporation), and 3,5,5-Trimethylhexanoyl peroxide (Perloyl (registered trademark) 355, manufactured by NOF Corporation) Diacyl peroxides such as: di-n-propyl peroxydicarbonate (Perloyl® NPP-50M, manufactured by NOF Corporation), diisopropyl peroxydicarbonate (Perloyl® IPP-50, manufactured by NOF Corporation), bis(4-t-butylcyclohexyl) peroxydicarbonate (Perloyl® TCP, manufactured by NOF Corporation), di-2-ethoxyethyl peroxydicarbonate (Perloyl® EEP, manufactured by NOF Corporation), di-2-ethoxyhexyl peroxydicarbonate (Perloyl Peroxydicarbonates such as Perloyl® OPP (manufactured by NOF Corporation), di-2-methoxybutyl peroxydicarbonate (Perloyl® MBP (manufactured by NOF Corporation), and di(3-methyl-3-methoxybutyl) peroxydicarbonate (Perloyl® SOP (manufactured by NOF Corporation)); hydroperoxides such as t-butyl hydroperoxide (Perbutyl® H-69 (manufactured by NOF Corporation)) and 1,1,3,3-tetramethylbutyl hydroperoxide (Perocta® H (manufactured by NOF Corporation));Dialkyl peroxides such as di-t-butyl peroxide (Perbutyl® D, manufactured by NOF Corporation), 2,5-dimethyl-2,5-bis(t-butylperoxy)hexane (Perhexa® 25B, manufactured by NOF Corporation); α,α'-bis(neodecanoylperoxy)diisopropylbenzene (Dipper® ND, manufactured by NOF Corporation), cumyl peroxyneodecanoate (Permil® ND, manufactured by NOF Corporation), 1,1,3,3-tetramethylbutyl peroxyneodecanoate (Perocta® ND, manufactured by NOF Corporation) (Manufactured by NOF Corporation), 1-Cyclohexyl-1-methylethyl peroxyneodecanoate (Percyclo(registered trademark) ND, manufactured by NOF Corporation), t-Hexyl peroxyneodecanoate (Perhexyl(registered trademark) ND, manufactured by NOF Corporation), t-Butyl peroxyneodecanoate (Perbutyl(registered trademark) ND, manufactured by NOF Corporation), t-Hexyl peroxypivalate (Perhexyl(registered trademark) PV, manufactured by NOF Corporation), t-Butyl peroxypivalate (Perbutyl(registered trademark) PV, manufactured by NOF Corporation), 1,1,3,3-Tetramethylbutyl peroxy-2-ethylhexyl Sanoate (Perocta® O, manufactured by NOF Corporation), 2,5-dimethyl-2,5-bis(2-ethylhexanoylperoxy)hexane (Perhexa® 250, manufactured by NOF Corporation), 1-cyclohexyl-1-methylethylperoxy-2-ethylhexanoate (Percyclo® O, manufactured by NOF Corporation), t-hexylperoxy 2-ethylhexanoate (Perhexyl® O, manufactured by NOF Corporation), t-butylperoxy 2-ethylhexanoate (Perbutyl® O, manufactured by NOF Corporation), t-butylperoxyisobutyl Examples of organic peroxides include peroxyesters such as peroxy esters (Perbutyl® IB, manufactured by NOF Corporation), t-hexyl peroxyisopropyl monocarbonate (Perhexyl® I, manufactured by NOF Corporation), and t-butyl peroxymalic acid (Perbutyl® MA, manufactured by NOF Corporation), t-amyl peroxy 2-ethylhexanoate (Trigonox® 121, manufactured by Kayaku Akzo Corporation), and t-amyl peroxy 3,5,5-trimethylhexanoate (Kaya Ester® AN, manufactured by Kayaku Akzo Corporation). These thermal radical generators may be used individually or in combination of two or more.

[0042] From the viewpoint of suppressing discoloration, the content of the thermal radical generator in the curable composition of this embodiment is preferably 1 part by mass or less, preferably 0.5 parts by mass or less, and more preferably 0.1 parts by mass or less, based on 100 parts by mass of the total mass of compound (A) and compound (B) described above.

[0043] (Other ingredients) In addition to the components described above, the curable composition of this embodiment may contain other components as needed, such as polymerization inhibitors, solvents, and inorganic fillers.

[0044] <Polymerization inhibitor> From the viewpoint of further improving the stability of the curable composition of this embodiment, it is preferable to incorporate a compound that suppresses radical reactions as a polymerization inhibitor. Examples of such compounds include, but are not limited to, phosphorus compounds such as triphenylphosphine and triphenyl phosphite; p-methoxyphenol, hydroquinone, pyrogallol, naphthylamine, tert-butylcatechol, cuprous chloride, 2,6-di-tert-butyl-p-cresol, 2,2'-methylenebis(4-ethyl-6-tert-butylphenol), 2,2'-methylenebis(4-methyl-6-tert-butylphenol), N-nitrosophenylhydroxylamine aluminum salt, and diphenylnitrosamine; tertiary amines such as benzyldimethylamine, 2-(dimethylaminomethyl)phenol, 2,4,6-tris(diaminomethyl)phenol, and diazabicycloundecene; and imidazoles such as 2-methylimidazole, 2-ethyl-4-methylimidazole, 2-ethylhexylimidazole, 2-undecylimidazole, and 1-cyanoethyl-2-methylimidal.

[0045] Of the phosphorus compounds mentioned above, triphenyl phosphite is preferred because it has a high inhibitory effect on radical reactions and is liquid at room temperature, making it easy to handle. When a phosphorus compound (especially triphenyl phosphite) is incorporated into the curable composition of this embodiment, the amount of phosphorus compound (especially triphenyl phosphite) incorporated is preferably 0.1 parts by mass or more from the viewpoint of inhibiting radical reactions, and preferably 10 parts by mass or less from the viewpoint of curability, based on 100 parts by mass of the total mass of compound (A) and compound (B) described above.

[0046] Among polymerization inhibitors, N-nitrosophenylhydroxylamine aluminum salt is preferred because it has a high inhibitory effect on radical reactions even in small amounts and produces excellent color tones in the resulting cured product. When a radical polymerization inhibitor (especially N-nitrosophenylhydroxylamine aluminum salt) is incorporated into the curable composition of this embodiment, the amount of radical polymerization inhibitor (especially N-nitrosophenylhydroxylamine aluminum salt) is preferably 0.0001 parts by mass or more from the viewpoint of radical polymerization inhibitory effect, and preferably 0.1 parts by mass or less from the viewpoint of curability, based on 100 parts by mass of the total mass of compound (A) and compound (B) described above.

[0047] Among the tertiary amines, benzyldimethylamine is preferred because it has a high inhibitory effect on radical reactions even in small amounts, and is liquid at room temperature, making it easy to handle. When incorporating tertiary amines (especially benzyldimethylamine) into the curable composition of this embodiment, the amount of tertiary amines (especially benzyldimethylamine) is preferably 0.001 parts by mass or more from the viewpoint of radical polymerization inhibition, and 5 parts by mass or less from the viewpoint of heat resistance, based on 100 parts by mass of the total mass of compound (A) and compound (B) described above.

[0048] <Solvent> Furthermore, the curable composition of this embodiment may contain a solvent as needed. Any conventionally known solvent can be used. In order to prevent foaming during curing and molding, and to prevent residual solvent in the cured product, the solvent content is preferably 90% by mass or less, and more preferably 80% by mass or less, based on the total amount of the curable composition.

[0049] <Inorganic filler> The curable composition of this embodiment may contain an inorganic filler. In order to avoid adverse effects on light transmittance, the inorganic filler is preferably one with an average particle size less than or equal to the wavelength used in the intended application, and more preferably one with an average particle size of 100 nm or less. In the curable composition of this embodiment, inorganic fillers can improve mechanical properties, thermal conductivity, and refractive index. There is no particular lower limit to the average particle size of the inorganic filler, but it is preferable that it be 0.1 nm or larger in order to lower the viscosity of the curable composition of this embodiment and ensure good moldability. The above average particle size is a value that can be calculated from the specific surface area of ​​BET. The amount of inorganic filler in the curable composition of this embodiment can be selected according to the purpose, but is preferably 1 to 60 parts by mass, more preferably 5 to 60 parts by mass, and even more preferably 5 to 40 parts by mass, based on 100 parts by mass of the total components other than the inorganic filler in the curable composition.

[0050] <Additives> The curable composition of this embodiment may contain various additives such as heat stabilizers, antioxidants, light stabilizers, ultraviolet absorbers, lubricants, antistatic agents, mold release agents, foaming agents, nucleating agents, colorants, crosslinking agents, dispersion aids, plasticizers, and flame retardants. These additives can be mixed with other components of the curable composition using known methods, such as centrifugation, and it is preferable to remove bubbles from the resulting mixture using known methods, such as vacuum degassing.

[0051] [Cured product] The cured product of this embodiment is the cured product of the curable composition of this embodiment described above, and the value of b / a, where b (Abs.) is the absorbance of the cured product to light with a wavelength of 426 nm and a (mm) is the optical path length for measuring the absorbance, is preferably 0.3 or less, more preferably 0.25 or less, and even more preferably 0.2 or less. A b / a value of 0.3 or less increases the transmittance of light with wavelengths of 400nm to 420nm, suppressing discoloration of the cured product. The b / a value can be measured by the method described in the examples below. The b / a value can be controlled to the above-mentioned numerical range by performing a photocuring process using a photoradical generator (C) during the preparation of the cured product.

[0052] The cured product of this embodiment preferably has a refractive index of 1.75 or higher, more preferably 1.77 or higher, and even more preferably 1.78 or higher, for light with a wavelength of 532 nm under a temperature of 25°C. A refractive index of 1.75 or higher allows it to exhibit excellent properties in optical component applications. The refractive index can be measured by the method described in the examples below. The refractive index can be controlled to the above-mentioned numerical range by performing a photocuring process using a photoradical generator (C) during the preparation of the cured product.

[0053] (Method of manufacturing a cured product) The method for manufacturing the cured product of this embodiment is: (A) A compound having three or more thiol groups in the molecule, (B) Compounds having two or more carbon-carbon unsaturated bonds in the molecule, (C) Photoradical generator and, A curable composition containing [the specified substance] is exposed to light in the wavelength range of 310 nm to 390 nm, with an integrated light intensity of 70 J / cm². 2 This process includes curing by irradiation in the following manner. The curable composition described above is the curable composition according to this embodiment. From the viewpoint of efficiently carrying out the curing reaction by light irradiation, irradiation may be carried out under an inert gas atmosphere such as nitrogen gas, or under an air atmosphere. In addition, if necessary, heat may be used as an energy source in combination, and the curable composition may be heated before irradiation with light. In the method for producing the cured product of this embodiment, light irradiation may be performed under heating conditions to promote the photocuring reaction, or curing may be performed by heating after light irradiation from the viewpoint of improving crosslink density.

[0054] In the method for manufacturing the cured product of this embodiment, visible light, ultraviolet light, far ultraviolet light, etc., can be used in the light irradiation step. As a light source, for example, a light-emitting diode (LED) light source, a low-pressure or high-pressure mercury lamp, a fluorescent lamp, natural light, sunlight, a deuterium lamp, or discharge light of a rare gas such as argon, krypton, or xenon, a YAG laser, an argon laser, a carbon dioxide laser, or an excimer laser such as XeF, XeCl, XeBr, KrF, KrCl, ArF, or ArCl can be used. The method for manufacturing the cured product in this embodiment is excellent at suppressing heat generation originating from the light source, and the amount of radical generation can be controlled by adjusting the illuminance and wavelength, so it is preferable to use a light-emitting diode (LED) light source. It is preferable that the LED light source emits light at a single emission wavelength. A single-emission wavelength LED light source has a narrow full width at half maximum at the emission wavelength, and the amount of radical generation can be controlled by adjusting the wavelength. Furthermore, from the viewpoint of increasing the transmittance of light rays with wavelengths of 400 nm to 420 nm in the cured product and suppressing yellowing, an LED light source having an emission peak wavelength of 350 to 380 nm is more preferable, and an LED light source having an emission peak wavelength of 360 to 380 nm is even more preferable.

[0055] When curing with a light-emitting diode light source having the above emission peak wavelength of 350 to 380 nm, it is preferable that the photo radical generator (C) contained in the curable composition has an absorption maximum in the range of 300 nm or more and 400 nm or less of the above wavelength, and the value of the gram absorption coefficient at a wavelength of 365 nm is 0.2 L / (g·cm) or less. By such a combination of the light source and the type of the photo radical generator (C), the transmittance of light rays with wavelengths of 400 nm to 420 nm can be further increased, and yellowing is further suppressed.

[0056] In the method for producing a cured product of the present embodiment, when exposing in the light irradiation step, the illuminance of light in the wavelength range of 310 nm or more and 390 nm or less is 1 mW / cm 2 ~200 mW / cm 2 It is preferable to be. By setting the illuminance to 1 mW / cm 2 or more, the exposure time can be shortened, so the productivity is improved. By setting it to 200 mW / cm 2 or less, side reactions tend to be suppressed, which is preferable. In the irradiation of light in the wavelength range of 310 nm or more and 390 nm or less, the integrated light quantity is preferably 70 J / cm 2 or less, more preferably 50 J / cm 2 or less, and even more preferably 20 J / cm 2 . In particular, by setting it to 20 J / cm 2 or less, the generation of coloring components due to side reactions can be effectively suppressed, and the cured product has excellent transparency. However, the mechanism of transparency reduction is not limited to the above.

[0057] In the method for producing a cured product of the present embodiment, there are no particular restrictions on the conditions when heating the curable composition and the cured product, and known conditions can be adopted. The curing temperature can be set variously, but from the viewpoints of curing rate and moldability, 30°C to 300°C is preferable, and 60°C to 200°C is more preferable.

[0058] (Use of the cured product) The curable composition and cured product of this embodiment can be suitably used in various applications where excellent refractive index, colorless transparency, and solvent resistance are required. For example, various optical components described later can be cited. That is, the optical components of this embodiment include the cured product of this embodiment described above.

[0059] <Coating agent> By coating a desired substrate with the curable composition of this embodiment and curing it, a coating layer can be obtained as an optical component. As a base material, various known materials can be appropriately selected and used, such as inorganic base materials like glass, iron, aluminum, copper, and ITO, and organic base materials like polyethylene resin (PE), polypropylene resin (PP), polyethylene terephthalate resin (PET), polyethylene naphthalate resin (PEN), polymethyl methacrylate resin (PMMA), polystyrene resin (PSt), polycarbonate resin (PC), and acrylonitrile-butadiene-styrene resin (ABS). By coating with a curable composition and curing it with ultraviolet light, a coating layer can be formed on light guide plates, polarizing plates, liquid crystal panels, EL panels, PDP panels, OHP films, optical fibers, color filters, optical disc substrates, lenses, plastic substrates for liquid crystal cells, prisms, and the like. Furthermore, if the refractive index of the cured product obtained from the curable composition is higher than that of the substrate, an anti-reflective effect can be imparted.

[0060] <Adhesive> An optical component having an adhesive layer can be obtained by interposing the curable composition of this embodiment between predetermined substrates and then curing the curable composition. As the substrate, the same materials as those described above for coating layer formation can be used. Since a transparent adhesive layer can be obtained by bonding with the curable composition described above, liquid crystal panels, EL panels, PDP panels, color filters, optical disc substrates, etc., can be suitably manufactured.

[0061] <Sealing materials and microlenses> By applying the curable composition of this embodiment to a predetermined area or pouring it into a predetermined mold and then curing it, a molded material sealed with a transparent cured material can be obtained as an optical component. Such molded materials are particularly suitable for light-emitting elements, light-receiving elements, recording elements, semiconductor circuit elements, optical-electrical circuit elements, waveguides, optical elements, displays, biosensors, and the like.

[0062] <Nanoimprint> By applying the curable composition of this embodiment to a predetermined area, placing a nanoimprint mold on the curable composition, curing it, and then releasing the mold, a transparent molded material can be obtained as an optical component. Nanoimprint transfer patterns can produce L / S, grids, pillars, holes, and the like. Such molded materials are particularly suitable for optical component applications such as light-emitting elements, photodetectors, and optical transmission-related components.

[0063] <Transparent substrate> By impregnating a glass cloth (substrate) with the curable composition of this embodiment and curing it, a transparent substrate can be obtained as an optical component. Various types of glass cloth known to the public can be appropriately selected and used. As the glass cloth, various fabrics obtained from various known glass fibers (strands, yarns, rovings, etc., composed of E-glass, C-glass, ECR-glass, T-glass, etc.) can be used, but glass cloth made from E-glass is preferred because it is inexpensive and readily available. The method for impregnating the glass cloth with the curable composition is not particularly limited, and various known methods can be employed, or a coating method may be used. Furthermore, in order to make the resulting transparent substrate colorless and transparent, it is preferable to make the difference in refractive index between the cured product obtained from the curable composition and the glass cloth 0.02 or less, more preferably 0.01 or less, and even more preferably the same. Furthermore, the impregnation properties of the glass cloth can be further improved by diluting the curable composition with a solvent. The ratio of the curable composition to the glass cloth can be appropriately determined depending on the application of the resulting transparent substrate, and is usually 20 to 500 parts by mass per 100 parts by mass of glass cloth. The thickness of the resulting transparent substrate can also be appropriately determined depending on the application, and is usually 20 μm to 1 mm. The transparent substrate obtained by impregnating a glass cloth with the above-described curable composition and curing it has excellent transparency and heat resistance, making it suitable for creating coating layers on light guide plates, polarizing plates, liquid crystal panels, EL panels, PDP panels, color filters, optical disc substrates, plastic substrates for liquid crystal cells, and the like. [Examples]

[0064] The present invention will be described in detail below with reference to specific examples and comparative examples, but the present invention is not limited in any way by the following examples and comparative examples. The methods for measuring and evaluating the physical properties in the examples and comparative examples are as follows.

[0065] [Measurement of b / a] For the cured products of the curable compositions prepared in the examples and comparative examples described later, the transmittance of light from 350 to 800 nm was measured using a transmittance measuring device (Hitachi High-Technologies Corporation, Spectrophotometer U-4100), and the absorbance of light at a wavelength of 426 nm was extracted as b (Abs.). In addition, the thickness of the prepared cured product was measured at four arbitrary points within the transmittance measurement range using a constant-pressure thickness measuring instrument (Teclock Corporation, Model: PF-01J), and the calculated average thickness was used as the measured optical path length a (mm) to calculate b / a.

[0066] [Transparency (average internal transmittance of light with wavelengths of 400nm to 760nm and average internal transmittance of light with wavelengths of 400nm to 420nm)] For the cured products of the curable compositions prepared in the examples and comparative examples, the transmittance of light from 350 to 800 nm was measured using a transmittance measuring device (Hitachi High-Technologies Corporation, Spectrophotometer U-4100). The average value (%) of the internal transmittance of light with wavelengths from 400 nm to 760 nm was extracted, and then the average value (%) of the internal transmittance of light with wavelengths from 400 nm to 420 nm was extracted. The transmittance of light with wavelengths of 400nm to 760nm was evaluated as ○ if it was 90% or higher, and × if it was less than 90%. The transmittance of light at wavelengths of 400nm to 420nm was evaluated as follows: ○ for 90% or higher, △ for 85% or higher but less than 90%, and × for less than 85%.

[0067] [Refractive Index Measurement] The refractive index of the cured products of the curable compositions prepared in the examples and comparative examples was measured at a wavelength of 532 nm using a prism coupler (Metricon, Model 2010) installed in a constant temperature chamber at 25°C.

[0068] [Solvent resistance] The cured products of the curable compositions prepared in the examples and comparative examples were immersed in N-methylpyrrolidone (NMP) at 25°C for 30 minutes, then removed, lightly rinsed with water, and wiped clean to perform a solvent resistance test. The test samples used were rectangular, with a long side of 2 cm and a short side of 1 cm. The mass of the cured material was measured before and after the solvent resistance test, and the mass loss rate was calculated to evaluate the solvent resistance. We determined that the closer the mass loss rate calculated below is to 0, the better the solvent resistance. Mass reduction rate = Mass of cured product after solvent resistance test / Mass of cured product before solvent resistance test ○: Mass reduction rate is less than 3%. ×: Mass reduction rate is 3% or more.

[0069] [Example 1] A curable composition was obtained by mixing 64 parts by mass of 1,3,5-benzenetrithiol (manufactured by Tokyo Chemical Industry Co., Ltd.) as compound (A), 33 parts by mass of tetravinylsilane (manufactured by Aldrich) as compound (B), and 3 parts by mass of 2-hydroxy-2-methylpropiophenone (manufactured by Tokyo Chemical Industry Co., Ltd., Gram absorbance coefficient at a wavelength of 365 nm in acetonitrile solution: 0.064 L / (g·cm), absorption maximum wavelength in the range of 300 nm to 400 nm: 330 nm) as a radical generator (C), and mixing at 60°C for 10 minutes. The curable composition is applied to an alkali-free glass substrate, and light with a wavelength of 365 nm is applied using a UV-LED lamp (Kessil PR160L-370) to obtain an integrated light intensity of 16 J / cm². 2 The material was irradiated in such a manner to obtain a cured product. The cumulative light intensity was calculated from the illuminance at wavelengths from 310 nm to 390 nm and the cumulative irradiation time, as measured by an ultraviolet light meter (UVD-C365, manufactured by Ushio Inc.). The resulting curable composition was heated in an oven at 120°C for 3 hours to improve the crosslinking density, and then peeled off the substrate to produce a cured product with a film thickness of 0.5 mm.

[0070] [Example 2] 1-hydroxycyclohexylphenyl ketone (manufactured by Tokyo Chemical Industry Co., Ltd., Gram absorbance coefficient at 365 nm in acetonitrile solution: 0.082 L / (g·cm), absorption maximum wavelength in the range of 300 nm to 400 nm: 331 nm) was used as the radical generator (C). Under other conditions, the curable composition and cured product were obtained by the same procedure as in Example 1.

[0071] [Example 3] Tetravinylgermane was used as compound (B). Curable composition and cured product were obtained using the same procedure as in Example 1 under the same conditions. Tetravinylgermane was synthesized by referring to the synthesis method disclosed in the literature "J. Chem. Soc., Dalton Trans., 1974, 2537-2542".

[0072] [Example 4] Hexa-vinyldigermann was used as compound (B). Under the same procedure as in Example 1, a curable composition and cured product were obtained. Hexa-vinyldigermann was synthesized by referring to the synthesis method disclosed in the literature "J. Chem. Soc., Dalton Trans., 1974, 2537-2542".

[0073] [Example 5] As the radical generator (C), 2,4-diethylthioxanthene-9-one (manufactured by Tokyo Chemical Industry Co., Ltd., Gram absorbance coefficient at a wavelength of 365 nm in acetonitrile solution: 19 L / (g·cm), absorption maximum wavelength in the range of 300 nm to 400 nm: 385 nm) was used. Under other conditions, the same procedure as in Example 1 was followed to obtain the curable composition and cured product.

[0074] [Example 6] Irradiation using a UV-LED lamp resulted in an integrated light output of 33 J / cm². 2 The procedure was carried out in such manner. Under the same procedure as in Example 1, a curable composition and a cured product were obtained.

[0075] [Example 7] Irradiation using a UV-LED lamp with an accumulated light intensity of 65 J / cm² 2 The procedure was carried out in such manner. Under the same procedure as in Example 1, a curable composition and a cured product were obtained.

[0076] (Comparative Example 1) 1,3-Benzenedithiol (manufactured by Tokyo Chemical Industry Co., Ltd.) was used as compound (A). Under the same procedure as in Example 1, a curable composition and cured product were obtained.

[0077] (Comparative Example 2) A curable composition was obtained by blending 71 parts by mass of 1,3,5-benzenetrithiol (manufactured by Tokyo Chemical Industry Co., Ltd.) as compound (A), 29 parts by mass of tetravinylsilane (manufactured by Aldrich) as compound (B), and 2 parts by mass of t-amyl peroxy-2-ethylhexanoate (manufactured by Kayaku Akzo Co., Ltd.: trade name "Trigonox® 121-50E"), a thermal radical generator, as a radical generator. A curable composition was applied to an alkali-free glass substrate, heated and cured in an oven at 120°C for 3 hours, and then peeled off the substrate to obtain a cured product with a thickness of 0.5 mm.

[0078] [Table 1]

Claims

1. (A) A compound having three or more thiol groups in the molecule, (B) A compound having two or more carbon-carbon unsaturated bonds in the molecule, (C) Photoradical generator and It contains, The compound (A) is an aromatic thiol, The aforementioned compound (B) One or more atoms selected from the group consisting of silicon atoms, germanium atoms, and tin atoms. In contrast, vinyl group, vinyl ether group, allyl group, allyl ether group and norbornyl A curable composition, which is a compound having a structure in which one or more groups selected from the group consisting of groups are directly bonded.

2. The aforementioned compound (B) It comprises one or more selected from the group consisting of tetravinylsilane, phenyltrivinylsilane, methyltrivinylsilane, hexanyldisilane, tetravinylgermane, phenyltrivinylgermane, methyltrivinylgermane, and hexanyldigermane. The curable composition according to claim 1.

3. The aforementioned photoradical generator (C) A compound having an absorption maximum in the wavelength range of 300 nm to 400 nm, and a Gram extinction coefficient of 0.2 L / (g·cm) or less at a wavelength of 365 nm. The curable composition according to claim 1.

4. A cured product of a curable composition according to any one of claims 1 to 3, When the absorbance for light with a wavelength of 426 nm is b (Abs.) and the optical path length for measuring the absorbance is a (mm), the value of b / a is 0.3 or less. cured product.

5. Under a temperature of 25°C, the refractive index for light with a wavelength of 532 nm is 1.75 or higher. The cured product according to claim 4.

6. An optical component comprising the cured product described in claim 5.

7. (A) A compound having three or more thiol groups in the molecule, (B) A compound having two or more carbon-carbon unsaturated bonds in the molecule, (C) Photoradical generator and It contains, The compound (A) is an aromatic thiol, The aforementioned compound (B) A curable composition having a structure in which one or more atoms selected from the group consisting of silicon atoms, germanium atoms, and tin atoms are directly bonded to one or more groups selected from the group consisting of vinyl groups, vinyl ether groups, allyl groups, allyl ether groups, and norbornyl groups is exposed to light in the wavelength range of 310 nm to 390 nm, with an integrated light intensity of 70 J / cm². ２ The process includes curing by irradiation as follows: A method for manufacturing a cured product.

8. The process includes a step of curing the curable composition using a light-emitting diode light source having an emission peak wavelength of 350 to 380 nm. A method for producing a cured product according to claim 7.

9. The aforementioned photoradical generator (C) A compound having an absorption maximum in the wavelength range of 300 nm to 400 nm, and a Gram extinction coefficient of 0.2 L / (g·cm) or less at a wavelength of 365 nm. A method for producing a cured product according to claim 8.

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