Composition, cured product thereof, molded product, display device, and solid-state imaging device

Abstract

Provided is a composition which is capable of forming a cured product having a high refractive index and which has excellent film-forming properties. The composition contains a compound (A) having at least one thiirane group or thietanyl group, a compound (B) having at least one (meth) acryloyl group, and a basic catalyst (C), and the compound (B) contains a compound having at least one (meth) acryloyl group and having a urethane bond in the molecule.

Description

Technical Field

[0001] The present invention relates to a composition and its cured product, molded product, display device, and solid-state imaging device. Background Art

[0002] In the field of optical devices, there is an urgent need for high-refractive-index materials. Lenses can be obtained using high-refractive-index materials, and the optical path within an optical device can be controlled using the lenses. Lenses are used in solid-state imaging devices for the purpose of improving the light condensing efficiency of each photoelectric conversion element, and also in display devices for the purpose of improving the light extraction efficiency from pixels. Conventionally, various high-refractive-index materials have been developed (for example, Patent Document 1).

[0003] Prior Art Documents

[0004] Patent Documents

[0005] Patent Document 1: International Publication No. 2011 / 102258 Summary of the Invention

[0006] However, in conventional curable compositions, due to differences in the main components, unevenness, shrinkage holes, and other defects may occur during film formation, and the film-forming property is sometimes insufficient.

[0007] Therefore, the main object of the present invention is to provide a composition that can form a cured product exhibiting a high refractive index and has excellent film-forming properties.

[0008] The present invention provides the composition according to [1] to [4], the molded product according to [5], the cured product according to [6], the display device according to [7], and the solid-state imaging device according to [8].

[0009] [1] A composition containing:

[0010] Compound (A) having at least one thiiranyl or thietanyl group,

[0011] Compound (B) having at least one (meth)acryloyl group, and

[0012] A basic catalyst (C),

[0013] The above compound (B) includes a compound having at least one (meth)acryloyl group and having a urethane bond in the molecule.

[0014] [2] The composition according to [1], wherein the above compound (B) is a compound having at least one (meth)acryloyl group and not having an acidic functional group.

[0015] [3] The composition according to [1] or [2], further containing a polymerization inhibitor (D).

[0016] [4] The composition according to any one of [1] to [3], wherein the compound (A) is a compound represented by the formula (A-1).

[0017]

[0018] [In the formula (A-1),

[0019] L represents a single bond or a divalent group, and two Ls may be the same or different.

[0020] A 1 represents an oxygen atom or a sulfur atom, and two As 1 may be the same or different. However, at least one of the two As 1 is a sulfur atom.

[0021] m represents 0 or 1, and two ms may be the same or different.

[0022] n represents any integer from 0 to 6.

[0023] R 1 represents a monovalent substituent. When there are a plurality of Rs 1 , the plurality of Rs 1 may be the same or different.

[0024] R 2 represents a hydrogen atom or a monovalent substituent, and two Rs 2 may be the same or different. ]

[0025] [5] A molded article obtained by curing the composition according to any one of [1] to [4].

[0026] [6] A cured product which is a cured product of the composition according to any one of [1] to [4].

[0027] [7] A display device comprising the cured product according to [6].

[0028] [8] A solid-state imaging device comprising the cured product according to [6].

[0029] According to the present invention, there is provided a composition capable of forming a cured product having a high refractive index and excellent film-forming properties. The thick film-forming properties, solvent resistance, etc. of the composition in some embodiments are also excellent. In addition, according to the present invention, there are provided a molded article using such a composition, a cured product of such a composition, a display device comprising the cured product, and a solid-state imaging device comprising the cured product. Detailed embodiments

[0030] Hereinafter, embodiments of the present invention will be described in detail. However, the present invention is not limited to the following embodiments.

[0031] In this specification, a numerical range indicated by "~" represents a range including the numerical values described before and after "~" as the minimum value and the maximum value, respectively. In the numerical ranges described in sections in this specification, the upper limit value or the lower limit value described in one numerical range can be replaced with the upper limit value or the lower limit value of another numerically described range. In addition, in the numerical ranges described in this specification, the upper limit value or the lower limit value of the numerical range can be replaced with the value shown in the examples.

[0032] In this specification, (meth)acrylate means acrylate or its corresponding methacrylate. The same applies to other similar expressions such as (meth)acryloyl and (meth)acrylate.

[0033] In this specification, the materials exemplified below can be used alone or in combination of two or more within the range where conditions are met, unless otherwise specified. When there are multiple corresponding substances in each component, the content of each component refers to the total amount of these multiple substances, unless otherwise specified.

[0034] <Composition>

[0035] A composition according to one embodiment contains compound (A) (hereinafter sometimes referred to as "(A) component"), compound (B) (hereinafter sometimes referred to as "(B) component"), and a basic catalyst (C) (hereinafter sometimes referred to as "(C) component"). Compound (A) has at least one thiiranyl group or thietanyl group, and compound (B) has at least one (meth)acryloyl group. The composition according to this embodiment can form a cured product having a high refractive index. In addition, the composition according to this embodiment has excellent film-forming properties. The composition according to this embodiment may further contain a polymerization inhibitor (D) and the like.

[0036] (A) Component: A compound having at least one thiiranyl group or thietanyl group

[0037] The composition according to this embodiment contains the (A) component. The (A) component can be a curable compound. By including the (A) component in the composition, the (A) component itself or the (A) component and the (B) component can be polymerized to form a cured product having a high refractive index. In this specification, a compound having at least one thiiranyl group or thietanyl group and at least one (meth)acryloyl group is included in the (A) component.

[0038] (A) The component can be used without particular limitation as long as it is a compound having at least one thiiranyl or thietanyl group. The component (A) can be, for example, a compound having at least one group represented by the formula (X0), and preferably a compound having at least one group represented by the formula (X1).

[0039]

[0040] In the formula (X0),

[0041] m represents 0 or 1.

[0042] R 2 represents a hydrogen atom or a monovalent substituent.

[0043] * represents the bonding position.

[0044]

[0045] In the formula (X1),

[0046] L represents a single bond or a divalent group.

[0047] m represents 0 or 1.

[0048] R 2 represents a hydrogen atom or a monovalent substituent.

[0049] * represents the bonding position.

[0050] Examples of the divalent group represented by L include a divalent aliphatic chain hydrocarbon group which may have a substituent; a divalent alicyclic hydrocarbon group which may have a substituent; a divalent aromatic hydrocarbon group which may have a substituent; a divalent hydrocarbon group composed of a combination thereof (e.g., an arylalkylene group), etc. The methylene group (—CH2—) contained in the divalent group may be substituted with —O—, —S—, —NR A —(R A represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms), —CO— or —SO2—.

[0051] Examples of the divalent aliphatic chain hydrocarbon group include a saturated or unsaturated aliphatic chain hydrocarbon group. More specifically, examples include methylene, vinyl, propanediyl, butanediyl, pentanediyl, hexanediyl, heptanediyl, octanediyl, nonanediyl, decanediyl, undecanediyl, dodecanediyl, tridecanediyl, tetradecanediyl, pentadecanediyl, hexadecanediyl, heptadecanediyl, octadecanediyl, nonadecanediyl, icosanediyl, etc. The divalent aliphatic chain hydrocarbon group may be linear or branched. The number of carbon atoms of the divalent aliphatic chain hydrocarbon group is usually 1 to 20, preferably 1 to 10, more preferably 1 to 6, further preferably 1 to 4, and particularly preferably 1 or 2.

[0052] Examples of the substituent that can be an aliphatic chain hydrocarbon group with a valence of 2 include halogen atoms such as fluorine atom, chlorine atom, bromine atom, iodine atom; hydroxyl group; amino group; acetyl group; cyano group, etc.

[0053] Examples of the divalent alicyclic hydrocarbon group include saturated or unsaturated alicyclic hydrocarbon groups. More specifically, monocyclic alicyclic hydrocarbon groups such as cyclopropanediyl, cyclobutanediyl, cyclopentanediyl, cyclohexanediyl, cyclooctanediyl, cyclononanediyl, cyclodecanediyl; polycyclic alicyclic hydrocarbon groups such as bicyclo[1.1.0]butanediyl, tricyclo[2.2.1.0]heptanediyl, bicyclo[3.2.1]octanediyl, bicyclo[2.2.2]octanediyl, adamantanediyl, bicyclo[4.3.2]undecanediyl, tricyclo[5.3.1.1]dodecanediyl, etc. The number of carbon atoms of the divalent alicyclic hydrocarbon group is usually 3 to 20, preferably 3 to 10, more preferably 3 to 6, and further preferably 5 or 6.

[0054] Examples of the substituent that can be a divalent alicyclic hydrocarbon group include alkyl groups having 1 to 10 carbon atoms (preferably 1 to 4 carbon atoms) such as methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group; halogen atoms such as fluorine atom, chlorine atom, bromine atom, iodine atom; hydroxyl group; amino group; acetyl group; cyano group, etc.

[0055] The divalent aromatic hydrocarbon group can be monocyclic or polycyclic. Examples of the divalent aromatic hydrocarbon group include phenylene group, naphthylene group, anthracenediyl group, fluorenylene group, etc. The number of carbon atoms of the divalent aromatic hydrocarbon group is usually 6 to 20, preferably 6 to 10.

[0056] Examples of the substituent that can be a divalent aromatic hydrocarbon group include alkyl groups having 1 to 10 carbon atoms (preferably 1 to 4 carbon atoms) such as methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group; halogen atoms such as fluorine atom, chlorine atom, bromine atom, iodine atom; hydroxyl group; amino group; acetyl group; cyano group, etc.

[0057] Examples of the monovalent substituent represented by R 2 include monovalent hydrocarbon groups such as monovalent aliphatic chain hydrocarbon groups that can have substituents, monovalent alicyclic hydrocarbon groups that can have substituents, monovalent aromatic hydrocarbon groups that can have substituents, and monovalent groups composed of combinations thereof (such as aralkyl groups); monovalent heterocyclic groups that can have substituents; hydroxyl group; amino group that can be substituted by one or two alkyl groups having 1 to 6 carbon atoms in amino group, monomethylamino group, monoethylamino group, dimethylamino group, diethylamino group, methylethylamino group, etc.; halogen atom; nitro group; cyano group; carboxyl group; sulfo group; mercapto group; formyl group; -SF3 group; -SF5 group. The methylene group (-CH2-) contained in the monovalent substituent can be replaced by -O-, -S-, -NRB -(R B is substituted by a hydrogen atom or an alkyl group having 1 to 6 carbon atoms), -CO-, or -SO2-. It should be noted that examples of the group in which the methylene group (-CH2-) contained as a monovalent substituent is substituted by -O- include alkoxy groups having 1 to 12 carbon atoms such as methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, heptyloxy, and octyloxy; and alkoxyalkyl groups such as methoxymethyl, ethoxymethyl, and methoxyethyl.

[0058] Examples of the monovalent aliphatic chain hydrocarbon group include saturated or unsaturated aliphatic chain hydrocarbon groups. More specifically, examples include alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, and eicosyl. The monovalent aliphatic chain hydrocarbon group can be linear or branched. The number of carbon atoms of the monovalent aliphatic chain hydrocarbon group is usually 1 to 20, preferably 1 to 10, more preferably 1 to 6, further preferably 1 to 4, and particularly preferably 1 or 2.

[0059] Examples of the substituent that can have a monovalent aliphatic chain hydrocarbon group include halogen atoms such as fluorine atom, chlorine atom, bromine atom, and iodine atom; hydroxyl group; amino group; acetyl group; and cyano group.

[0060] Examples of the monovalent alicyclic hydrocarbon group include saturated or unsaturated alicyclic hydrocarbon groups. More specifically, examples include monocyclic alicyclic hydrocarbon groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclooctyl, cyclononyl, and cyclodecyl; and polycyclic alicyclic hydrocarbon groups such as bicyclo[1.1.0]butyl, tricyclo[2.2.1.0]heptyl, bicyclo[3.2.1]octyl, bicyclo[2.2.2]octyl, adamantyl, bicyclo[4.3.2]undecyl, and tricyclo[5.3.1.1]dodecyl. The number of carbon atoms of the monovalent alicyclic hydrocarbon group is usually 3 to 20, preferably 3 to 10, more preferably 3 to 6, further preferably 5 or 6.

[0061] Examples of the substituent that can have a monovalent alicyclic hydrocarbon group include alkyl groups having 1 to 10 (preferably 1 to 4 carbon atoms) such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, and decyl; halogen atoms such as fluorine atom, chlorine atom, bromine atom, and iodine atom; hydroxyl group; amino group; acetyl group; and cyano group.

[0062] The monovalent aromatic hydrocarbon group can be monocyclic or polycyclic. Examples of the monovalent aromatic hydrocarbon group include phenyl, naphthyl, anthryl, and fluorenyl. The number of carbon atoms of the monovalent aromatic hydrocarbon group is usually 6 to 20, preferably 6 to 10.

[0063] Examples of the substituent that can be an aromatic hydrocarbon group having a valence of 1 include alkyl groups having 1 to 10 carbon atoms (preferably 1 to 4 carbon atoms) such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, and decyl; halogen atoms such as fluorine atom, chlorine atom, bromine atom, and iodine atom; hydroxyl group; amino group; acetyl group; cyano group, etc.

[0064] Examples of the monovalent heterocyclic group include pyrrolidinyl, pyrrolinyl, imidazolidinyl, imidazolinyl, oxolinyl, thiazolyl, piperidinyl, morpholinyl, piperazinyl, indolyl, isoindolyl, quinolinyl, thienyl, pyrrolyl, furyl, etc., which are aliphatic heterocyclic groups having 4 to 20 carbon atoms or aromatic heterocyclic groups having 3 to 20 carbon atoms.

[0065] Examples of the substituent that can be a monovalent heterocyclic group include alkyl groups having 1 to 10 carbon atoms (preferably 1 to 4 carbon atoms) such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, and decyl; halogen atoms such as fluorine atom, chlorine atom, bromine atom, and iodine atom; hydroxyl group; amino group; acetyl group; cyano group, etc.

[0066] m represents 0 or 1. When m is 0, it represents a three-membered ring structure of thiiranyl, and when m is 1, it represents a four-membered ring structure of thietanyl. m is preferably 0.

[0067] From the viewpoint of the high refractive index of the cured product, the component (A) preferably contains a compound having an aromatic ring. Examples of the aromatic ring include aromatic hydrocarbon rings such as benzene ring, naphthalene ring, and anthracene ring; aromatic heterocycles such as furan ring, pyrrole ring, benzofuran ring, thiophene ring, benzothiophene ring, indole ring, pyridine ring, quinoline ring, isoquinoline ring, pyridazine ring, pyrimidine ring, and triazine ring. The aromatic ring is preferably a benzene ring or a naphthalene ring, more preferably a naphthalene ring.

[0068] From the viewpoint of the high refractive index of the cured product, the component (A) is preferably a compound represented by the formula (A-1) (hereinafter, sometimes referred to as "compound (A-1)").

[0069]

[0070] In the formula (A-1),

[0071] L represents a single bond or a divalent group, and the two Ls may be the same or different.

[0072] A 1 represents an oxygen atom or a sulfur atom, and the two As 1 may be the same or different. However, at least one of the two As 1 is a sulfur atom.

[0073] m represents 0 or 1, and the two ms may be the same or different.

[0074] n represents any integer from 0 to 6.

[0075] R 1 represents a monovalent substituent. When there are multiple Rs, 1 the multiple Rs 1 may be the same or different.

[0076] R 2 represents a hydrogen atom or a monovalent substituent. The two Rs 2 may be the same or different.

[0077] In compound (A-1), the two groups represented by formula (X) can be bonded at any position from 1 to 8 of the naphthalene ring. The groups represented by formula (X) on the naphthalene ring can, for example, be bonded at any two positions from 1 to 4 (5 to 8), or can be bonded at any one position from 1 to 4 (5 to 8) and any one position from 5 to 8 (1 to 4). The groups represented by formula (X) on the naphthalene ring are preferably bonded at any one position from 1 to 4 (5 to 8) and any one position from 5 to 8 (1 to 4).

[0078]

[0079] In formula (X), L, A 1 , m and R 2 represent the same meaning as described above, and * represents the bonding position.

[0080] When compound (A-1) has one or more monovalent substituents represented by R 1 , the monovalent substituents represented by R 1 can be bonded at any position from 1 to 8 of the naphthalene ring except for the bonding position of the group represented by formula (X).

[0081] L represents a single bond or a divalent group. The two Ls can be the same or different. In compound (A-1), at least one of the two Ls is preferably an alkanediyl group, and more preferably both are alkanediyl groups. In this case, the number of carbon atoms of the alkanediyl group is preferably from 1 to 10, more preferably from 1 to 6, further preferably from 1 to 4, and particularly preferably 1 or 2.

[0082] A 1 represents an oxygen atom or a sulfur atom. The two As 1 can be the same or different. However, at least one of the two As 1 is a sulfur atom. In compound (A-1), the two As 1 are preferably both sulfur atoms. As the number of sulfur atoms as A 1 increases, a cured product with a higher refractive index can be formed, and there is a tendency for better curability.

[0083] m represents 0 or 1, and the two m's can be the same or different. In the compound (A-1), the two m's are preferably both 0.

[0084] n represents any integer from 0 to 6. n is preferably any integer from 0 to 3, more preferably any integer from 0 to 2, still more preferably 0 or 1, and particularly preferably 0.

[0085] R 1 represents a monovalent substituent. When there are a plurality of R's, 1 the plurality of R's 1 can be the same or different. Examples of the monovalent substituent represented by R 1 include the same substituents as those represented by R 2 .

[0086] R 2 represents a hydrogen atom or a monovalent substituent, and the two R's 2 can be the same or different. In the compound (A-1), the two R's 2 are preferably a hydrogen atom or a monovalent aliphatic chain hydrocarbon group, more preferably a hydrogen atom or a monovalent aliphatic chain hydrocarbon group having 1 to 6 carbon atoms, still more preferably a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and particularly preferably a hydrogen atom, a methyl group or an ethyl group.

[0087] Examples of the component (A) (compound (A-1)) include compounds represented by formula (Aa), formula (Ab), formula (Ac), formula (Ad), formula (Ae) and formula (Af). L, A in formula (Aa), formula (Ab), formula (Ac), formula (Ad), formula (Ae) and formula (Af) 1 , m, n, R 1 and R 2 have the same meanings as described above.

[0088]

[0089] In formula (Aa), formula (Ab), formula (Ac), formula (Ad), formula (Ae) and formula (Af), at least one of the two L's is preferably an alkanediyl group, and more preferably both are alkanediyl groups. In this case, the number of carbon atoms of the alkanediyl group is preferably 1 to 10, more preferably 1 to 6, still more preferably 1 to 4, and particularly preferably 1 or 2.

[0090] In formula (Aa), formula (Ab), formula (Ac), formula (Ad), formula (Ae) and formula (Af), the two m's are each independently 0 or 1, and are preferably 0. In formula (Aa), formula (Ab), formula (Ac), formula (Ad), formula (Ae) and formula (Af), the two m's are preferably both 0.

[0091] In formula (Aa), formula (Ab), formula (Ac), formula (Ad), formula (Ae) and formula (Af), n is each independently any integer from 0 to 6, preferably any integer from 0 to 3, more preferably any integer from 0 to 2, still more preferably 0 or 1, and particularly preferably 0.

[0092] In formula (Aa), formula (Ab), formula (Ac), formula (Ad), formula (Ae) and formula (Af), two A's 1 are each independently an oxygen atom or a sulfur atom. However, at least one of the two A's 1 is a sulfur atom. A 1 Preferably, both are sulfur atoms.

[0093] In formula (Aa), formula (Ab), formula (Ac), formula (Ad), formula (Ae) and formula (Af), two R's 2 are each independently preferably a hydrogen atom or a monovalent aliphatic chain hydrocarbon group, more preferably a hydrogen atom or a monovalent aliphatic chain hydrocarbon group having 1 to 6 carbon atoms, still more preferably a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and particularly preferably a hydrogen atom, a methyl group or an ethyl group. The two R's 2 are preferably the same.

[0094] Specific examples of compound (A-1) are shown below, but are not limited thereto.

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103] From the viewpoint of synthesis, the molecular weight of component (A) is preferably 2000 or less, more preferably 1000 or less, and still more preferably 750 or less. From the viewpoint of volatility, the molecular weight of component (A) is preferably 50 or more, more preferably 100 or more, and still more preferably 150 or more.

[0104] The compound (A-1) as the component (A) can be obtained by synthesizing the compound represented by the formula (A-1a) (hereinafter sometimes referred to as "compound (A-1a)") and reacting the compound (A-1a) with a sulfurizing agent.

[0105]

[0106] In the formula (A-1a), L, m, n, R 1 and R 2 have the same meanings as those represented by the above (formula (A-1)).

[0107] The compound (A-1a) can be obtained, for example, by a method including a step of reacting the compound represented by the formula (A-2) (hereinafter sometimes referred to as "compound (A-2)") with the compound represented by the formula (A-3) (hereinafter sometimes referred to as "compound (A-3)").

[0108]

[0109] In the formula (A-2), n and R 1 have the same meanings as those described above.

[0110]

[0111] In the formula (A-3), L, m and R 2 have the same meanings as those described above, and X represents a leaving group.

[0112] The reaction of the compound (A-2) and the compound (A-3) can be carried out, for example, in the presence of a base. Examples of the base include inorganic bases such as sodium hydroxide, potassium hydroxide, lithium hydroxide, cesium hydroxide, sodium carbonate, potassium carbonate, lithium carbonate, cesium carbonate, sodium hydride, lithium aluminum hydride, sodium borohydride, sodium bicarbonate, potassium bicarbonate, lithium bicarbonate, cesium bicarbonate; metal alkoxides such as sodium methoxide, potassium methoxide, lithium methoxide, sodium ethoxide, potassium ethoxide, sodium isopropoxide, potassium isopropoxide, sodium tert-butoxide, potassium tert-butoxide; organic bases such as ammonia, methylamine, dimethylamine, trimethylamine, triethylamine, diisopropylethylamine, triisopropylamine, DBU (1,8-diazabicyclo[5.4.0]undec-7-ene), DABCO (1,4-diazabicyclo[2.2.2]octane), pyridine, 2,6-dimethylpyridine, 2,6-di-tert-butylpyridine, dimethylaminopyridine, triphenylphosphine, tetramethylammonium bromide, tetramethylammonium chloride. The amount of the base used can be, for example, 0.0001 to 10 moles, preferably 0.001 to 5 moles, more preferably 0.01 to 4 moles, and further preferably 0.1 to 3 moles relative to 1 mole of the compound (A-2).

[0113] In addition, two or more types of bases can also be used in combination. In the case of using in combination, carbonates such as sodium carbonate, potassium carbonate, lithium carbonate, cesium carbonate, or bicarbonates such as sodium bicarbonate, potassium bicarbonate, lithium bicarbonate, cesium bicarbonate, and metal hydroxides such as sodium hydroxide, potassium hydroxide, lithium hydroxide, cesium hydroxide, or metal alkoxides such as sodium methoxide, potassium methoxide, lithium methoxide, sodium ethoxide, potassium ethoxide, sodium isopropoxide, potassium isopropoxide, sodium tert-butoxide, potassium tert-butoxide are preferably used, and a combination of a bicarbonate and a metal hydroxide is more preferred. In the case of using in combination, the two can be added simultaneously or stepwise.

[0114] In the compound (A-3), as the leaving group represented by X, halogen atoms such as fluorine atom, chlorine atom, bromine atom, iodine atom can be mentioned; alkylsulfonyl groups such as methylsulfonyl group, ethylsulfonyl group, propylsulfonyl group, butylsulfonyl group, trifluoromethylsulfonyl group, perfluoroethylsulfonyl group, perfluoropropylsulfonyl group, perfluorobutylsulfonyl group; aromatic sulfonyl groups such as benzenesulfonyl group, p-toluenesulfonyl group, p-fluorobenzenesulfonyl group, pentafluorobenzenesulfonyl group, etc. As a specific example of the compound (A-3), a halohydrin compound (a compound in which L is a methylene group, m is 0, R 2 is a hydrogen atom, and X is a halogen atom) can be mentioned. The amount of the compound (A-3) used can be, for example, 0.01 to 20 moles, preferably 0.5 to 15 moles, relative to 1 mole of the compound (A-2). In this step, the reaction can be carried out using two or more types of the compound (A-3).

[0115] The reaction of the compound (A-2) and the compound (A-3) is preferably carried out in a solvent. As the solvent, in addition to water, organic solvents such as ketones, aromatic hydrocarbons, halogenated aromatic hydrocarbons, aliphatic hydrocarbons, halogenated aliphatic hydrocarbons, ethers, alcohols, glycol dimethyl ethers, esters, aliphatic nitriles, sulfoxides, amides, etc. can be mentioned. As the organic solvent, the following solvents are exemplified.

[0116] Ketones: acetone, methyl ethyl ketone, diethyl ketone, butyl methyl ketone, diisobutyl ketone, methyl isobutyl ketone, methyl isopentyl ketone, 2-heptanone, 2-octanone, cyclopentanone, cyclohexanone, etc.;

[0117] Aromatic hydrocarbons: benzene, toluene, xylene, mesitylene, naphthalene, anisole, nitrobenzene, aniline, tetralin, durene, etc.;

[0118] Halogenated aromatic hydrocarbons: chlorobenzene, dichlorobenzene, chloronaphthalene, etc.;

[0119] Aliphatic hydrocarbons: pentane, hexane, heptane, etc.;

[0120] Halogenated aliphatic hydrocarbons: dichloromethane, chloroform, 1,2-dichloroethane, tetrachloroethane, tetrachloroethylene, etc.;

[0121] Ethers: diethyl ether, diisopropyl ether, methyl tert-butyl ether, cyclopentyl methyl ether, diphenyl ether, dimethoxyethane, di alkanes, etc.;

[0122] Alcohols: methanol, ethanol, propanol, isopropanol, butanol, tert-butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, hexafluoroisopropanol, etc.;

[0123] Glycol dimethyl ethers: methyl diglycol dimethyl ether, ethyl diglycol dimethyl ether, triglycol dimethyl ether, diethylene glycol butyl methyl ether, etc.;

[0124] Esters: methyl acetate, ethyl acetate, propyl acetate, butyl acetate, etc.;

[0125] Aliphatic nitriles: acetonitrile, etc.;

[0126] Sulfoxides: dimethyl sulfoxide, sulfolane, etc.;

[0127] Amides: N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, etc.

[0128] The temperature of the reaction between compound (A-2) and compound (A-3) can be, for example, -80 to 200 °C, preferably -40 to 150 °C, more preferably -20 to 120 °C, and further preferably -5 to 100 °C.

[0129] By doing so, compound (A-1a) can be obtained. When using compound (A-1a) obtained in the synthesis of compound (A-1), compound (A-1a) can be used after separation or directly without separation.

[0130] Compound (A-1) can be obtained, for example, by a method including a step of reacting compound (A-1a) with a sulfurizing agent.

[0131] The reaction of compound (A-1a) with a sulfurizing agent is a reaction in which the sulfurizing agent substitutes the oxygen atom of the epoxy ring or oxetanyl ring in compound (A-1a) with a sulfur atom to form a thiirane ring (episulfide ring) or a thietane ring. Examples of the sulfurizing agent include thiourea, methylthiourea, dimethylthiourea, trimethylthiourea, tetramethylthiourea, tetraethylthiourea, ethylenethiourea, phenylthiourea, diphenylthiourea, tolylthiourea, xylylthiourea, sodium thiocyanate, potassium thiocyanate, etc. The amount of the sulfurizing agent used can be arbitrarily adjusted according to the oxygen atom to be substituted. The amount of the sulfurizing agent used is, for example, 0.01 to 20 moles, preferably 0.5 to 10 moles, relative to 1 mole of compound (A-1a). In addition, by adjusting the amount of the sulfurizing agent used, the reaction temperature, the reaction time, etc., two oxygen atoms in compound (A-1a) can be substituted with sulfur atoms, or one oxygen atom in compound (A-1a) can be substituted with a sulfur atom.

[0132] The reaction of compound (A-1a) with a sulfurizing agent is preferably carried out in a solvent. Examples of the solvent include the same solvents as those exemplified in the reaction of compound (A-2) and compound (A-3). The reaction of compound (A-1a) with a sulfurizing agent can be, for example, -80 to 200 °C, preferably -40 to 100 °C, more preferably -20 to 80 °C, and further preferably -5 to 60 °C.

[0133] In order to inhibit the polymerization of the generated compound (A-1), a polymerization inhibitor can also be added to the reaction system. Examples of the polymerization inhibitor include acids, acid anhydrides, etc. More specifically, examples include:

[0134] inorganic acidic compounds such as nitric acid, hydrogen chloride (hydrochloric acid), perchloric acid, hypochlorous acid, chlorine dioxide, hydrofluoric acid, sulfuric acid, fuming sulfuric acid, thionyl chloride, boric acid, arsenic acid, arsenous acid, pyroarsenic acid, phosphoric acid, phosphorous acid, hypophosphorous acid, phosphorus oxychloride, phosphorus oxybromide, phosphorus sulfide, phosphorus trichloride, phosphorus tribromide, phosphorus pentachloride, hydrocyanic acid, chromic acid, nitric anhydride, sulfuric anhydride, boron oxide, arsenic pentoxide, phosphorus pentoxide, chromic anhydride, silicon dioxide, aluminum oxide, aluminum chloride, zinc chloride, lithium hydrogen phosphate, sodium hydrogen phosphate, potassium hydrogen phosphate, cesium hydrogen phosphate, lithium dihydrogen phosphate, sodium dihydrogen phosphate, potassium dihydrogen phosphate, cesium dihydrogen phosphate;

[0135] Organic carboxylic acids such as formic acid, acetic acid, peracetic acid, thioacetic acid, oxalic acid, tartaric acid, propionic acid, butyric acid, succinic acid, valeric acid, caproic acid, caprylic acid, naphthenic acid, methyl mercaptopropionate, malonic acid, glutaric acid, adipic acid, cyclohexanecarboxylic acid, thiodipropionic acid, dithiodipropionic acid acetate, maleic acid, benzoic acid, phenylacetic acid, o-toluic acid, m-toluic acid, p-toluic acid, salicylic acid, 2-methoxybenzoic acid, 3-methoxybenzoic acid, benzoylbenzoic acid, phthalic acid, isophthalic acid, terephthalic acid, benzilic acid, α-naphthalenecarboxylic acid, β-naphthalenecarboxylic acid, acetic anhydride, propionic anhydride, butyric anhydride, succinic anhydride, maleic anhydride, benzoic anhydride, phthalic anhydride, pyromellitic dianhydride, trimellitic anhydride, trifluoroacetic anhydride, etc.;

[0136] Phosphoric acids such as monomethyl phosphate, dimethyl phosphate and trimethyl phosphate, monoethyl phosphate, diethyl phosphate and triethyl phosphate, monoisobutyl phosphate, diisobutyl phosphate and triisobutyl phosphate, monobutyl phosphate, dibutyl phosphate and tributyl phosphate, monolauryl phosphate, dilauryl phosphate and trilauryl phosphate, etc., and phosphorous acids after a part of their phosphate esters is converted into phosphite esters;

[0137] Organophosphorus compounds such as dialkyldithiophosphoric acids represented by dimethyldithiophosphoric acid, etc.;

[0138] Phenols such as phenol, catechol, tert-butylcatechol, 2,6-di-tert-butyl-p-cresol, 2,6-di-tert-butylethylphenol, resorcinol, hydroquinone, phloroglucinol, pyrogallol, cresol, ethylphenol, butylphenol, nonylphenol, hydroxyphenylacetic acid, hydroxyphenylpropionic acid, hydroxyphenylacetamide, methyl hydroxyphenylacetate, ethyl hydroxyphenylacetate, hydroxyphenylethanol, hydroxyphenylethylamine, hydroxybenzaldehyde, phenylphenol, bisphenol-A, 2,2'-methylene-bis(4-methyl-6-tert-butylphenol), bisphenol-F, bisphenol-S, α-naphthol, β-naphthol, aminophenol, chlorophenol, 2,4,6-trichlorophenol, etc.;

[0139] Sulfonic acids such as methanesulfonic acid, ethanesulfonic acid, butanesulfonic acid, dodecanesulfonic acid, benzenesulfonic acid, o-toluenesulfonic acid, m-toluenesulfonic acid, p-toluenesulfonic acid, ethylbenzenesulfonic acid, butylbenzenesulfonic acid, dodecylbenzenesulfonic acid, p-phenolsulfonic acid, o-phenolsulfonic acid, m-benzoic acid, p-aminobenzenesulfonic acid, 4B-acid, diaminostilbenesulfonic acid, biphenylsulfonic acid, α-naphthalenesulfonic acid, β-naphthalenesulfonic acid, peri-acid, Laurent’s acid, phenyl J-acid, etc.

[0140] The amount of the polymerization inhibitor used may be, for example, 0.0001 to 1.0 mol, preferably 0.001 to 0.5 mol, more preferably 0.01 to 0.25 mol, and still more preferably 0.05 to 0.15 mol, relative to 1 mol of the compound (A-1). Among these, the polymerization inhibitor is preferably acetic acid, acetic anhydride, maleic acid, maleic anhydride, phosphoric acid, an alkali metal hydrogen phosphate or an alkali metal dihydrogen phosphate.

[0141] By washing the reaction product solution with an acidic aqueous solution, the time-dependent stability of the obtained compound (A-1) can be improved. Specific examples of the acid used in the acidic aqueous solution include the acids exemplified as the polymerization inhibitor above. The acid can be used alone or in combination of two or more. The acidic aqueous solution generally tends to exhibit an effect at a pH of 6 or lower, but a more effective range is a pH of 3 or lower. The acid used in the acidic aqueous solution is preferably an aqueous solution of hydrogen chloride (hydrochloric acid), sulfuric acid, phosphoric acid, and / or maleic acid.

[0142] Furthermore, in order to improve the stability of the compound (A-1), a hydrogen sulfide adsorbent can also be used. Examples of the hydrogen sulfide adsorbent include iron(III) hydroxide, zinc oxide, KNK-301 (a zinc oxide-based adsorbent, manufactured by Kureha Corporation), NIONON202A (an iron oxide-based adsorbent, manufactured by Ibuki Shoji Co., Ltd.), LIMONIC (an iron hydroxide-based, manufactured by Nippon Limonite Co., Ltd.), etc. The hydrogen sulfide adsorbent can be added during the reaction or can also be added and used during the purification after the reaction.

[0143] From the viewpoint of easily obtaining the effects of the present invention sufficiently, based on the total amount of the solid components of the composition, the content of the component (A) can be, for example, 30 to 98% by mass. Based on the total amount of the solid components of the composition, the content of the component (A) is preferably 40% by mass or more, more preferably 50% by mass or more, still more preferably 60% by mass or more, preferably 97% by mass or less, more preferably 95% by mass or less, and still more preferably 92% by mass or less.

[0144] The total amount of the solid components of the composition refers to the total of the components contained in the composition excluding the solvent. The content of each component in the solid components of the composition can be measured by known analytical means such as liquid chromatography and gas chromatography. The content of each component in the solid components of the composition can be calculated based on the formulation during the preparation of the composition.

[0145] (B) Component: A compound having at least one (meth)acryloyl group

[0146] The composition of the present embodiment contains component (B). Component (B) includes a compound having at least one (meth)acryloyl group and a urethane bond in the molecule (hereinafter sometimes referred to as “component (B1)”). By combining with component (A), component (B) (component (B1)) has a tendency that unevenness, shrinkage holes, etc. are less likely to occur during film formation, and a good cured film with few defects can be formed. In addition, by combining with component (A), component (B) (component (B1)) can increase the viscosity of the composition (thicken the composition), and by using this composition, a thick (for example, 1.0 μm or more) cured film can be formed. That is, the composition of the present embodiment is also excellent in thick film formability.

[0147] From the viewpoint of curability, component (B) is preferably a compound having at least one (meth)acryloyl group and no acidic functional group. Here, the acidic functional group refers to a group capable of releasing a carboxylic acid group (-COOH), a sulfonic acid group (-SO3H), a phosphoric acid group (-PO4H2), a boric acid group (-BO2H2), etc. protons (H + ). Among them, a group that cannot release protons such as carboxylate groups such as -COONa, sulfonate groups such as -SO3Na, phosphate groups such as -PO4Na2, borate groups such as -BO2Na2, etc. (the protons that can be released are substituted by alkali metal ions, etc.) is not included in the acidic functional group.

[0148] As component (B1), for example, urethane (meth)acrylate having a urethane bond in the molecule can be cited. Urethane (meth)acrylate is usually produced by reacting a (meth)acrylate having a hydroxyl group, a polyisocyanate, and a polyol added as needed.

[0149] As urethane (meth)acrylate, for example, urethane (meth)acrylate having a polyester structure in the molecule and urethane (meth)acrylate having a polyether structure in the molecule can be cited. As commercially available products of urethane (meth)acrylate, for example, NK Oligo U series, UA series, etc. manufactured by Shin-Nakamura Chemical Co., Ltd.; SUA series, RUA series, etc. manufactured by Asia Industries Co., Ltd.; UF series, AH series, etc. manufactured by Kyoeisha Chemical Co., Ltd.; R series, RST series, GX series, etc. manufactured by Daiichi Kogyo Seiyaku Co., Ltd.

[0150] From the viewpoint of synthesis, the molecular weight of component (B1) is preferably 100,000 or less, more preferably 20,000 or less, and further preferably 10,000 or less. From the viewpoint of volatility, component (B1) is preferably 100 or more, more preferably 300 or more, and further preferably 500 or more.

[0151] From the viewpoint of easily achieving the effects of the present invention, the content of the component (B1) is, for example, 30 to 100% by mass based on the total amount of the component (B). The content of the component (B1) is preferably 50 to 100% by mass, more preferably 70 to 100% by mass, and still more preferably 80 to 100% by mass based on the total amount of the component (B).

[0152] (B) component may further contain a compound having at least one (meth)acryloyl group and no urethane bond in the molecule (hereinafter sometimes referred to as “(B2) component”). Examples of the (B2) component include a monofunctional (meth)acrylate compound having one (meth)acryloyl group and no urethane bond in the molecule, and a polyfunctional (meth)acrylate compound having two or more (meth)acryloyl groups and no urethane bond in the molecule. The number of (meth)acryloyl groups in the polyfunctional (meth)acrylate compound is preferably 2 to 6, and more preferably 2 to 3.

[0153] Examples of the monofunctional (meth)acrylate compound having one (meth)acryloyl group and no urethane bond in the molecule include (meth)acrylic acid; (meth)acrylic acid methyl ester, (meth)acrylic acid ethyl ester, (meth)acrylic acid n-butyl ester, (meth)acrylic acid isobutyl ester, (meth)acrylic acid tert-butyl ester, (meth)acrylic acid n-pentyl ester, (meth)acrylic acid n-hexyl ester, (meth)acrylic acid n-octyl ester, (meth)acrylic acid isooctyl ester, (meth)acrylic acid 2-ethylhexyl ester, (meth)acrylic acid isodecyl ester, (meth)acrylic acid dodecyl ester ((meth)acrylic acid lauryl ester), (meth)acrylic acid isomyristyl ester, (meth)acrylic acid stearyl ester, acrylic acid isostearyl ester, etc., which are (meth)acrylic acid alkyl esters having an alkyl group; (meth)acrylic acid 3-butenyl ester, etc., which are (meth)acrylic acid alkenyl esters having an alkenyl group; (meth)acrylic acid benzyl ester, (meth)acrylic acid phenoxyethyl ester, etc., which are (meth)acrylic acid esters having an aromatic group; (meth)acrylic acid methoxytetraethylene glycol ester, (meth)acrylic acid methoxyhexaethylene glycol ester, (meth)acrylic acid methoxyoctaethylene glycol ester, (meth)acrylic acid methoxynonaethylene glycol ester, (meth)acrylic acid methoxypolyethylene glycol ester, (meth)acrylic acid methoxyheptapropylene glycol ester, (meth)acrylic acid ethoxytetraethylene glycol ester, (meth)acrylic acid butoxyethylene glycol ester, (meth)acrylic acid butoxydiethylene glycol ester, etc., which are (meth)acrylic acid alkoxypolyalkylene glycol esters; (meth)acrylic acid cyclohexyl ester, (meth)acrylic acid isobornyl ester, (meth)acrylic acid dicyclopentyl ester, etc., which are (meth)acrylic acid esters having an alicyclic group.

[0154] As a polyfunctional (meth)acrylate compound having two or more (meth)acryloyl groups and not having a urethane bond in the molecule, for example, a (meth)acrylate compound having two or more (meth)acryloyl groups and not having a urethane bond in the molecule, a (meth)acrylate compound having three or more (meth)acryloyl groups and not having a urethane bond in the molecule, etc. can be cited.

[0155] As a (meth)acrylate compound having two (meth)acryloyl groups and not having a urethane bond in the molecule, for example, 1,3-butanediol di(meth)acrylate, 1,3-butanediol mono(meth)acrylate, 1,6-hexanediol di(meth)acrylate, ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, polyethylene glycol diacrylate, bis(acryloyloxyethyl) ether of bisphenol A, epoxyethane-modified bisphenol A di(meth)acrylate, epoxypropane-modified neopentyl glycol di(meth)acrylate, epoxyethane-modified neopentyl glycol di(meth)acrylate, 3-methylpentanediol di(meth)acrylate, etc. can be cited.

[0156] (Meth)acrylate compounds having three or more (meth)acryloyl groups and not having a urethane bond in the molecule, examples of which include trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, tris(2-hydroxyethyl) isocyanurate tri(meth)acrylate, ethylene oxide-modified trimethylolpropane tri(meth)acrylate, propylene oxide-modified trimethylolpropane tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, tripentaerythritol tetra(meth)acrylate, tripentaerythritol penta(meth)acrylate, tripentaerythritol hexa(meth)acrylate, tripentaerythritol hepta(meth)acrylate, tripentaerythritol octa(meth)acrylate, reaction products of pentaerythritol tri(meth)acrylate and acid anhydride, reaction products of dipentaerythritol penta(meth)acrylate and acid anhydride, reaction products of tripentaerythritol hepta(meth)acrylate and acid anhydride, caprolactone-modified trimethylolpropane tri(meth)acrylate, caprolactone-modified pentaerythritol tri(meth)acrylate, caprolactone-modified tris(2-hydroxyethyl) isocyanurate tri(meth)acrylate, caprolactone-modified pentaerythritol tetra(meth)acrylate, caprolactone-modified dipentaerythritol penta(meth)acrylate, caprolactone-modified dipentaerythritol hexa(meth)acrylate, caprolactone-modified tripentaerythritol tetra(meth)acrylate, caprolactone-modified tripentaerythritol penta(meth)acrylate, caprolactone-modified tripentaerythritol hexa(meth)acrylate, caprolactone-modified tripentaerythritol hepta(meth)acrylate, caprolactone-modified tripentaerythritol octa(meth)acrylate, reaction products of caprolactone-modified pentaerythritol tri(meth)acrylate and acid anhydride, reaction products of caprolactone-modified dipentaerythritol penta(meth)acrylate and acid anhydride, reaction products of caprolactone-modified tripentaerythritol hepta(meth)acrylate and acid anhydride, etc.

[0157] The content of component (B2) is, based on the total amount of component (B), for example, 0 to 70% by mass. The content of component (B1) is, based on the total amount of component (B), preferably 0 to 50% by mass, more preferably 0 to 30% by mass, and still more preferably 0 to 20% by mass.

[0158] Considering that it is easy to fully obtain the effects of the present invention, the content of component (B) is, based on the total amount of the solid components of the composition, for example, 1 to 40% by mass. The content of component (B) is, based on the total amount of the solid components of the composition, preferably 2% by mass or more, more preferably 3% by mass or more, still more preferably 5% by mass or more, preferably 35% by mass or less, more preferably 30% by mass or less, and still more preferably 25% by mass or less.

[0159] Component (C): basic catalyst

[0160] The composition of this embodiment contains component (C). Component (C) is a component that releases a base for initiating anionic polymerization by using at least one of active energy ray irradiation and heat as needed. As component (C), ammonium salts, DBU (diazabicycloundecene) salts, DBN (diazabicyclononene ) salts, biguanide salts, aromatic salts, aromatic dimethylureas, aliphatic dimethylureas, guanidine salts, phosphazene salts, imidazole salts, etc. can be cited. Due to the difference in structure, at least one of active energy ray irradiation and heat can be used to initiate anionic polymerization. A compound that can release a base for initiating anionic polymerization by active energy ray irradiation is called a photo-base generator, and a compound that can release a base for initiating anionic polymerization by heat is called a thermal base generator.

[0161] In one embodiment, from the viewpoint of solvent resistance, component (C) preferably contains a DBU (diazabicycloundecene) salt. In one embodiment, from the viewpoints of the storage stability of the composition and the curability and heat resistance of the cured product, component (C) preferably contains at least one selected from guanidine salts and phosphazene salts.

[0162] As the anion constituting the salt, for example, inorganic anions, organic anions, etc. can be cited. As the anion, for example, hydroxide ions; halide ions such as chloride ions, bromide ions, iodide ions; carbonate ions; bicarbonate ions; nitrate ions; sulfate ions; sulfite ions; chromate ions; chromate ions; dichromate ions; phosphate ions; cyanide ions; permanganate ions; complex ions such as hexacyanoferrate(III) ions; organic carboxylic acid ions such as formate ions, acetate ions, propionate ions, butyrate ions, valerate ions, etc. can be cited. From the viewpoints of curability, heat resistance, light resistance, and storage stability, the anion is preferably an organic carboxylic acid ion. The number of carbon atoms constituting the organic carboxylic acid ion is preferably 1 to 20, more preferably 1 to 10.

[0163] From the viewpoint of improving curability and / or heat resistance, the content of component (C) is preferably 0.1 part by mass or more, more preferably 0.5 part by mass or more, relative to 100 parts by mass of the total amount of component (A). From the viewpoint of making the physical properties such as the mechanical properties of the cured product good, it is preferably 10 parts by mass or less, more preferably 8 parts by mass or less.

[0164] (D) Component: Polymerization inhibitor

[0165] The composition may contain one or more than two components (D). Whether to contain a polymerization inhibitor in the composition is preferably determined in consideration of the type of component (A). Component (D) is preferably a component that is dissolved or dispersed in a solvent. The component (D) contained in the composition may be added during the preparation of the composition or may be added after the production of component (A). By making the composition contain component (D), the unintended polymerization of component (A) is inhibited, thereby improving the storage stability of the composition.

[0166] Component (D) may be exemplified by the same substance as the polymerization inhibitor added to the reaction system to inhibit the polymerization of the generated compound (A-1). Component (D) is preferably an organic carboxylic acid, more preferably an organic carboxylic acid having 10 or less carbon atoms, and still more preferably formic acid or acetic acid.

[0167] When the composition contains component (D), from the viewpoint of improving the storage stability of the composition, the content of component (D) is preferably 0.01 part by mass or more, more preferably 0.1 part by mass or more, still more preferably 0.5 part by mass or more, particularly preferably 1 part by mass or more, preferably 100 parts by mass or less, more preferably 50 parts by mass or less, still more preferably 25 parts by mass or less, and particularly preferably 10 parts by mass or less, based on 100 parts by mass of the total amount of component (A).

[0168] As other components contained in the composition, for example, resins, curable compounds other than components (A) and (B), solvents, additives, etc. can be cited. As additives, for example, inorganic particles, fillers, polymerization initiators, thickeners, leveling agents, stabilizers, surfactants, antistatic agents, lubricants, antifouling agents, ultraviolet absorbers, antioxidants, dispersants, etc. can be cited.

[0169] (Resin)

[0170] The composition may contain one or more than two resins. By making the composition contain a resin, developability can be imparted to the cured product of the composition, or the mechanical properties and / or optical properties of the cured product and the molded product containing the same can be adjusted. As the resin, for example, a thermoplastic resin and a curable resin can be cited. The curable resin may be a photocurable resin cured by irradiation with active energy rays or a thermosetting resin cured by heat.

[0171] As thermoplastic resins, for example, olefin resins such as polyethylene resin, polypropylene resin, and polycycloolefin resin can be mentioned; (meth)acrylic resins such as poly(meth)acrylate resin; styrene resins such as polystyrene resin, styrene-acrylonitrile resin, and acrylonitrile-butadiene-styrene resin; vinyl resins such as polyvinyl chloride resin, vinylidene chloride resin, polyvinyl acetate resin, polyvinyl butyral resin, ethylene-vinyl acetate copolymer, and ethylene-vinyl alcohol resin; polyester resins such as polyethylene terephthalate resin, polybutylene terephthalate resin, and liquid crystal polyester resin; polyoxymethylene resin; polyamide resin; polycarbonate resin; polyurethane resin; polyphenylene sulfide resin, etc. One or more of these resins can be used as polymer blends or polymer alloys.

[0172] As curable resins, resins having a photopolymerizable group or a thermopolymerizable group can be mentioned. More specifically, for example, (meth)acrylic resins, epoxy resins, melamine resins, unsaturated polyester resins, phenolic resins, urea resins, alkyd resins, polyimide resins, etc. can be mentioned.

[0173] As other examples of resins, alkali-soluble resins can be mentioned. By making the composition contain an alkali-soluble resin, developability can be imparted to the cured product of the composition. An alkali-soluble resin means a resin soluble in an aqueous alkali solution. Specifically, for example, resins having a carboxyl group and / or a phenolic hydroxyl group can be mentioned.

[0174] From the viewpoint of improving the developability and solvent resistance of the cured product of the composition, the acid value of the alkali-soluble resin is preferably 10 to 170 mgKOH / g, more preferably 20 to 150 mgKOH / g, and further preferably 30 to 140 mgKOH / g. The acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of the alkali-soluble resin, and can be obtained, for example, by titration with an aqueous potassium hydroxide solution.

[0175] In addition, as other examples of resins, high refractive index resins can be mentioned. A high refractive index resin means that the refractive index at a wavelength of 550 nm is 1.60 or more.

[0176] The weight average molecular weight (Mw) in terms of standard polystyrene measured by gel permeation chromatography (GPC) of the resin can be, for example, 500 to 2 million, preferably 1000 to 1 million, and more preferably 1500 to 750,000. The Mw of the resin can be adjusted by appropriately combining reaction conditions such as the selection of raw materials used, charging methods, reaction temperature, and time.

[0177] When the composition contains a resin, the content of the resin is preferably 5% by mass or more, more preferably 10% by mass or more, preferably 80% by mass or less, and more preferably 70% by mass or less based on the total amount of the solid components of the composition.

[0178] (Curing compound other than component (A) and component (B))

[0179] The composition may further contain one or more curing compounds other than component (A) and component (B). By making the composition contain a curing compound other than component (A) and component (B), the viscosity or curability of the composition can be adjusted, and the mechanical properties and / or optical properties of the obtained cured product and the molded product containing the cured product can be adjusted.

[0180] Examples of the curing compound other than component (A) and component (B) include epoxy compounds other than component (A) and component (B), oxetane compounds other than component (A), hydroxy compounds, vinyl ether compounds, allyl compounds, thiol compounds, polyphenol compounds, isothiocyanate compounds, acid anhydrides, and the like.

[0181] When the composition contains a curing compound other than component (A) and component (B), the content of the curing compound other than component (A) and component (B) is preferably 1% by mass or more, more preferably 2% by mass or more, preferably 30% by mass or less, and more preferably 20% by mass or less based on the total amount of the solid components of the composition.

[0182] (Solvent)

[0183] The composition may contain one or more solvents. The solvent is preferably a solvent capable of dissolving or dispersing component (A), and more preferably a solvent capable of further dissolving or dispersing other components other than component (A). Examples of the solvent include the solvents (organic solvents) exemplified in the reaction of compound (A-2) and compound (A-3), ester solvents (solvents containing -COO- in the molecule and not containing -O-), ether solvents (solvents containing -O- in the molecule and not containing -COO-), ether ester solvents (solvents containing -COO- and -O- in the molecule), ketone solvents (solvents containing -CO- in the molecule and not containing -COO-), alcohol solvents (solvents containing OH in the molecule and not containing -O-, -CO-, and COO-), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfoxide, and the like.

[0184] Examples of ester solvents include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutyrate, ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, isoamyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexyl acetate, γ-butyrolactone, etc.

[0185] Examples of ether solvents include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenetole, methylanisole, etc.

[0186] Examples of ether ester solvents include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, ethyl 2-ethoxy-2-methylpropionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, etc.

[0187] Examples of ketone solvents include 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone, isophorone, etc.

[0188] Examples of alcohol solvents include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, glycerol, etc.

[0189] Examples of aromatic hydrocarbon solvents include benzene, toluene, xylene, mesitylene, etc.

[0190] Examples of amide solvents include N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, etc.

[0191] When the composition contains a solvent, the content of the solvent is preferably 60 parts by mass or more, more preferably 80 parts by mass or more, preferably 1000 parts by mass or less, and more preferably 500 parts by mass or less, relative to 100 parts by mass of the total amount of the solid components of the composition. When the composition contains a solvent, the solid component concentration of the composition is preferably 5 to 60% by mass, and more preferably 10 to 50% by mass.

[0192] <Cured product and molded product>

[0193] The cured product of one embodiment is the cured product of the composition. The molded product of one embodiment is a molded product obtained by curing the composition and contains the cured product of the composition. Since the composition has excellent film-forming properties, curability, etc., it can be suitably used as a curable material for producing a cured product or a molded product containing the cured product. The cured product can be obtained by curing the component (A), component (B), etc. in the composition by using at least one of irradiation with active energy rays and heat. The shape of the molded product containing the cured product is not particularly limited, and it may include a film (membrane) shape, plate shape, lens shape, powder shape, granular shape, non-spherical particle shape, crushed particle shape, porous shape, massive continuum, fibrous shape, tubular shape, hollow filament shape, etc., and can be any shape corresponding to the use of the molded product, etc.

[0194] As a method for obtaining a molded product from the composition, there is no particular limitation, and examples thereof include a method of forming a film on a substrate and then performing molding by etching, etc., an injection molding method, a casting polymerization molding method, etc.

[0195] In the casting polymerization molding method, for example, the composition is injected into a molding die, degassed as needed, and then cured by heating in an oven, and the obtained molded product is taken out. Further irradiating the taken-out molded product with active energy rays can also perform post-curing.

[0196] When forming a film as a molded product on a substrate, the composition is coated on the substrate, dried as needed to form a coating film (coating layer), and the coating film (coating layer) is cured, whereby a molded product as a cured film (cured layer) can be obtained. The molded product can also be a cured film (cured layer) with a patterned engraving. The cured film with a patterned engraving can be obtained by engraving a pattern by methods such as photolithography, inkjet method, printing method, etc. The pattern engraving method can be, for example, photolithography. Photolithography is a method of coating the composition on a substrate, drying as needed to form a coating film (coating layer), exposing the coating film (coating layer) through a photomask, and developing the exposed coating film (coating layer).

[0197] Examples of the substrate include glass plates such as quartz glass, borosilicate glass, aluminosilicate glass, soda-lime glass with a silica coating on the surface, and alkali-free glass; resin plates such as polycarbonate, polymethyl methacrylate, and polyethylene terephthalate; silicon; and substrates with aluminum, silver, silver / copper / palladium alloy thin films formed thereon. Examples of the method for coating the composition on the substrate include spin coating, slot coating, and slot and spin coating methods.

[0198] The light source used for exposure is preferably a light source that generates light with a wavelength of 250 to 450 nm. For example, depending on the absorption wavelength of the photoinitiator, light near 436 nm, near 408 nm, or near 365 nm can be selectively extracted from the light with wavelengths in these ranges using a bandpass filter. Specific examples of the light source include mercury lamps, light-emitting diodes, metal halide lamps, and halogen lamps. After pattern exposure, the exposed coating film (coating layer) can be heated (pre-bake before development) before development.

[0199] Examples of the developer used for development include aqueous solutions and solvents containing basic compounds such as potassium hydroxide, sodium bicarbonate, sodium carbonate, and tetramethylammonium hydroxide. As the solvent, for example, the solvents (organic solvents) exemplified in the reaction of compound (A-2) and compound (A-3) or the above solvents can be used. The developer may also contain a surfactant. Examples of the development method include spin immersion development, dipping development, and spraying development. The patterned cured film (cured layer) obtained by development can also be further heated (post-bake).

[0200] Since the cured product or the molded product containing the cured product is formed from the composition, it can exhibit a high refractive index. In addition, their refractive index can be controlled to a desired refractive index by adjusting the composition of the composition, etc. The refractive index of the cured product or the molded product containing the cured product at a wavelength of 550 nm can be 1.65 or more, 1.68 or more, 1.70 or more, 1.72 or more, or 1.73 or more. The refractive index of the cured product or the molded product containing the cured product at a wavelength of 550 nm is, for example, 2.00 or less, and can also be 1.90 or less.

[0201] The refractive index at a wavelength of 550 nm of the cured product or the molded product containing the cured product can be measured, for example, by the following method. First, a coating film is formed on a substrate, and the coating film is cured to obtain a substrate with a cured film formed thereon. Next, a visible ultraviolet spectrophotometer (for example, "V-650" manufactured by JASCO Corporation) equipped with an integrating sphere unit (for example, "ISV-922" manufactured by JASCO Corporation) is used to measure the transmission spectrum and the reflection spectrum at wavelengths from 300 nm to 800 nm for the substrate with the cured film formed thereon. Then, the increase and decrease caused by the interference of the reflection spectrum are subtracted from the transmission spectrum and the reflection spectrum for smoothing. In the resulting true reflection spectrum, the refractive index at a wavelength of 550 nm of the cured product or the molded product containing the cured product is calculated from the value at a wavelength of 550 nm and the refractive index of the substrate according to the Fresnel formula (for example, the original fifth edition of Hecht Optics I, published by Maruzen Publishing Co., Ltd. in 2018, pp. 209-226). Thus, the refractive index at a wavelength of 550 nm of the cured product or the molded product containing the cured product can be obtained.

[0202] <Usage>

[0203] Examples of the use as a cured product or a molded product include: glass substitutes and surface coating materials thereof; coating materials for window glass, daylighting glass, and light source protection glass for houses, facilities, transportation equipment, etc.; window films for houses, facilities, transportation equipment, etc.; interior and exterior decoration materials for houses, facilities, transportation equipment, etc., interior and exterior decorative paints, and coating films formed from such paints; alkyd resin paints and coating films formed from such paints; acrylic paints and coating films formed from such paints; components for light sources that generate ultraviolet rays such as fluorescent lamps and mercury lamps; shielding materials for electromagnetic waves generated by various displays, components for precision machinery, electronic and electrical equipment; containers or packaging materials for food, chemicals, pharmaceuticals, etc.; bottles, boxes, blister packs, cups, special packaging, optical disc coatings, agricultural or industrial sheets or films; anti-fading agents for printed matter, dyed matter, dyes, pigments, etc.; protective films for polymer supports (for example, for plastic components of mechanical and automotive parts); printed matter cover layers; inkjet medium films; matte laminated films; optical films; safety glass / front glass interlayers; electrochromic / photochromic uses; cover laminated films; solar heat control films; cosmetics such as sunscreen, shampoo, conditioner, hair styling agents, etc.; fiber products and fibers for clothing such as sportswear, socks, hats, etc.; interior household items such as curtains, carpets, wallpapers, etc.; medical devices such as plastic lenses, contact lenses, artificial eyes, etc.; optical supplies such as optical filters, backlight display films, prisms, lenses (for example, spectacle lenses, camera lenses, and microlenses, pickup lenses described later), mirrors, photographic materials, etc.; document materials such as mold films, transfer stickers, anti-graffiti films, tapes, inks, etc.; signboards, markers, etc. and surface coating materials thereof; substrates used in optical devices, etc.; optical waveguides; holograms; LED encapsulation materials, etc.

[0204] The molded article is suitable for use as an optical article, i.e., a lens, used in an optical device. Examples of the optical device include a solid-state imaging device, a display device, etc. In the solid-state imaging device, a lens for the purpose of improving the light condensing efficiency of each photoelectric conversion element can be used. In addition, in the display device, a lens for the purpose of improving the light extraction efficiency from pixels can be used. The lens may be a microlens. Examples of the display device include a liquid crystal display device, an organic EL display device, etc.

[0205] As the high refractive index material, inorganic compounds such as zirconia and titanium oxide have been conventionally known. However, in the case of producing a molded article containing a high refractive index material composed of an inorganic compound, there are cases where it is difficult to perform etching and other difficult-to-mold situations, and in addition, there is sometimes a problem of contamination due to the scattering of the high refractive index material during molding. Such problems can be solved by using an organic compound, i.e., the high refractive index material of the present embodiment.

[0206] The cured product of the composition of the present embodiment can be suitably used as a main chain scission type positive resist. In the formation of a resist pattern using the cured product of the composition of the present embodiment, by irradiation with ionizing radiation (e.g., electron beam, KrF laser, ArF laser, EUV laser, etc.), the main chain of the polymer of the component (A), the component (B), etc. constituting the cured product is cut in the irradiated portion of the resist film, becoming low molecular weight. Therefore, a difference in solubility with respect to the developer is generated between the exposed portion and the unexposed portion, and a resist pattern is formed. The resist pattern using the cured product of the composition of the present embodiment can be applied when forming a resist pattern in the manufacture of printed circuit boards such as stacked substrates; semiconductors; photomasks; molds, etc.

[0207] Examples

[0208] Hereinafter, the present invention will be described more specifically with reference to examples. However, the present invention is not limited to these examples. It should be noted that, hereinafter, unless otherwise specified, "parts" means "parts by mass".

[0209] [Synthesis Example 1]

[0210] <Synthesis of Compound (Aa-1)>

[0211] ·Synthesis of Compound (Aa-1a)

[0212]

[0213] Make the inside of a four-necked flask equipped with a coiled cooling tube and a thermometer into a nitrogen atmosphere. Add 30 parts of 1,6-naphthalenedithiol, 165 parts of acetone, 45 parts of pure water, and 139 parts of epichlorohydrin to the above flask and stir in an ice bath for 15 minutes. Next, add 15 parts of sodium hydroxide, 66 parts of acetone, and 203 parts of pure water to another flask and dissolve completely. Then, add the solution dropwise to the above four-necked flask over 1 hour. After the dropwise addition, raise the temperature to 30 °C and stir at 30 °C for 2 hours. Refine the resulting mixture to obtain 46 parts of the compound represented by the formula (Aa-1a) (compound (Aa-1a)).

[0214] Perform 1 H-NMR analysis and LC-MS determination to confirm the formation of compound (Aa-1a).

[0215] 1 H-NMR (deuterochloroform) δ: 8.37 - 8.39 (1H), 7.85 (1H), 7.39 - 7.70 (4H), 3.08 - 3.29 (5H), 2.94 - 2.98 (1H), 2.57 - 2.81 (3H), 2.39 - 2.41 (1H) LC-MS: [M+H] + = 305.5

[0216] · Synthesis of Compound (Aa-1)

[0217]

[0218] Make the inside of a four-necked flask equipped with a coiled cooling tube and a thermometer into a nitrogen atmosphere. Add 3 parts of compound (Aa-1a), 30 parts of methanol, 30 parts of toluene, 0.05 part of anhydrous acetic acid, and 3.8 parts of thiourea to the above flask and stir at room temperature for 24 hours. Refine the resulting mixture to obtain 2.5 parts of the compound represented by the formula (Aa-1) (compound (Aa-1)).

[0219] Perform 1 H-NMR analysis and LC-MS determination to confirm the formation of compound (Aa-1).

[0220] 1 H-NMR (deuterochloroform) δ: 8.39 - 8.43 (1H), 7.86 (1H), 7.40 - 7.74 (4H), 3.40 - 3.53 (2H), 3.04 - 3.18 (2H), 2.78 - 2.96 (2H), 2.47 - 2.49 (1H), 2.35 - 2.36 (1H), 2.14 - 2.16 (1H), 1.93 - 1.94 (1H) LC-MS: [M+H] + = 337.5

[0221] [Examples 1 - 8 and Comparative Examples 1, 2]

[0222] <Preparation of Composition>

[0223] The compounding ingredients shown in Table 1 were added to a flask in the addition amounts (unit: parts by mass) shown in Table 1, and stirred to prepare the compositions of Examples 1 to 8 and Comparative Examples 1 and 2 in a liquid state. It was confirmed that the compositions of Examples 1 to 8 and Comparative Examples 1 and 2 were transparent to the naked eye, and the compounding ingredients were uniformly dissolved.

[0224] The details of the abbreviations of the compounding ingredients shown in Table 1 are as follows.

[0225] Component (A): Compound (A) having at least one thiiranyl or thietanyl group

[0226] · (A-1): Compound (Aa-1) synthesized in Synthesis Example 1

[0227] Component (B): Compound (B) having at least one (meth)acryloyl group

[0228] Component (B1): Compound having at least one (meth)acryloyl group and having a urethane bond in the molecule

[0229] · (B1-1): Urethane acrylate (manufactured by Shin-Nakamura Chemical Co., Ltd., "NKOligoUA-122P", polyester type, number of functional groups: 2, molecular weight: 1100)

[0230] · (B1-2): Urethane acrylate (manufactured by Shin-Nakamura Chemical Co., Ltd., "NKOligoUA-160TM", polyether type, number of functional groups: 2, molecular weight: 1600)

[0231] · (B1-3): Urethane acrylate (manufactured by Asia Industries Co., Ltd., "SUA-023", polyether type, number of functional groups: 2)

[0232] · (B1-4): Urethane acrylate (manufactured by Asia Industries Co., Ltd., "RUA-049X", number of functional groups: 3)

[0233] · (B1-5): Urethane acrylate (manufactured by Kyoeisha Chemical Co., Ltd., "UF-8001G", number of functional groups: 2, molecular weight: 4500)

[0234] · (B1-6): Urethane acrylate (manufactured by Kyoeisha Chemical Co., Ltd., "AH-600")

[0235] · (B1-7): Urethane acrylate (manufactured by Daiichi Pharmaceutical Co., Ltd., "R-1204B-H")

[0236] (Component (B2)): A compound having at least one (meth)acryloyl group and no urethane bond in the molecule

[0237] ·(B2-1): An acrylate ester without a urethane bond (manufactured by Shin-Nakamura Chemical Co., Ltd., "NKEster A-9550")

[0238] (Component (C)): Basic catalyst (C)

[0239] ·(C-1): A DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) salt-type thermal anionic polymerization initiator (manufactured by San-apro Ltd., "U-CAT SA102")

[0240] (Component (D)): Polymerization inhibitor (D)

[0241] ·(D-1): Formic acid

[0242] Solvent

[0243] ·(E-1): PGMEA (propylene glycol monomethyl ether acetate)

[0244] <Evaluation test>

[0245] (1) Film-forming property

[0246] Approximately 3 mL of the compositions of Examples 1 to 8 and Comparative Examples 1 and 2 were respectively dropped onto an alkali-free glass plate (thickness 0.7 mm, manufactured by Corning Inc., "Eagle XG"), and spin-coated using a spin coater (manufactured by MIKASA Co., Ltd., "MS-B100") under the conditions of 1000 rpm and 20 seconds to form a coating film. The alkali-free glass plate having the coating film formed thereon was heated at 60°C for 2 minutes to remove the solvent.

[0247] The obtained coating film was observed, and the film-forming property of the composition was evaluated according to the following evaluation criteria. In the evaluation of the film-forming property, whether perforation defects occurred was evaluated. It should be noted that perforation defects refer to a state in which a portion of the alkali-free glass plate having a hole with a diameter of 1 mm or more is exposed on the coating film. A shrinkage defect refers to a state in which, although no portion of the alkali-free glass plate is exposed, the film thickness is locally thinned around environmental foreign matters or the like, resulting in a pit-shaped defect with a diameter of less than 1 mm. The results are shown in Table 2.

[0248] A: No perforation defects and shrinkage defects occurred.

[0249] B: No perforation defects occurred, but shrinkage defects occurred.

[0250] D: Both perforation defects and shrinkage defects occurred.

[0251] (2) Formation of cured film

[0252] About 3 mL of the compositions of Examples 1 to 8 and Comparative Examples 1 and 2 were respectively dropped onto an alkali-free glass plate (thickness 0.7 mm, manufactured by Corning, "Eagle XG"), and spin-coated under the conditions of 1000 rpm and 20 seconds using a spin coater (manufactured by MIKASA Co., Ltd., "MS-B100") to form a coating film. The alkali-free glass plate having the coating film formed thereon was heated at 60 °C for 2 minutes to remove the solvent. Then, using a high-pressure mercury lamp proximity UV exposure apparatus (manufactured by Ushio Electric Co., Ltd., "UV-3300SC"), exposure was carried out on the alkali-free glass plate having the coating film formed thereon in an atmospheric atmosphere with an irradiation energy of 1000 mJ / cm 2 Next, the alkali-free glass plate having the anti-coating film formed thereon after exposure was heated at 120 °C for 5 minutes as post-baking to obtain an alkali-free glass plate having a cured film formed thereon.

[0253] (3) Measurement of refractive index

[0254] For the alkali-free glass substrate having the cured film formed in (2) above, a visible ultraviolet spectrophotometer (manufactured by JASCO Corporation, "V-650") equipped with an integrating sphere unit (manufactured by JASCO Corporation, "ISV-922") was used to measure the transmission spectrum and reflection spectrum at wavelengths from 300 nm to 800 nm. The increase and decrease caused by the interference of the reflection spectrum were subtracted and smoothed from the transmission spectrum and reflection spectrum. In the resulting true reflection spectrum, the refractive index of the cured film at a wavelength of 550 nm was calculated from the value at a wavelength of 550 nm and the refractive index of the alkali-free glass plate (manufactured by Corning, "Eagle XG") according to the Fresnel formula (Original fifth edition of Hecht Optics I, published by Maruzen, 2018, p. 209-226). The results are shown in Table 2.

[0255] (4) Thick film formability

[0256] The film thickness of the cured film obtained in (2) above was measured, and the thick film formability of the composition was evaluated according to the following evaluation criteria. The film thickness was measured using a stylus profilometer (manufactured by Bruker Corporation, "DekTak XT") for the cured film on the alkali-free glass plate. It should be noted that when measuring the cured film obtained in Comparative Example 1, the result was 1.5 μm.

[0257] A: The film thickness is 1.65 μm or more.

[0258] B: The film thickness is 1.45 μm or more and less than 1.65 μm.

[0259] D: The film thickness is less than 1.45 μm.

[0260] (5) Solvent resistance (film thickness retention rate)

[0261] Using the alkali-free glass plate with a cured film formed therein obtained in the above (2), the solvent resistance (film thickness retention rate) of the composition was evaluated according to the following evaluation criteria. The solvent resistance was evaluated by immersing the alkali-free glass plate with a cured film formed therein in acetone at 23°C for 10 minutes, observing the change in the appearance of the cured film before and after immersion, and calculating the film thickness retention rate before and after immersion (film thickness retention rate = film thickness of the cured film after immersion / film thickness of the cured film before immersion). The results are shown in Table 2.

[0262] A: No change in appearance, and the film thickness retention rate is 90% to 100%.

[0263] B: No change in appearance, and the film thickness retention rate is less than 90% and 80% or more.

[0264] D: No change in appearance, and the film thickness retention rate is less than 80%.

[0265] [Table 1]

[0266]

[0267] [Table 2]

[0268]

[0269] As shown in Table 2, the composition of the example is superior to the composition of the comparative example in terms of film-forming property and refractive index. In addition, the thick film-forming property, solvent resistance, etc. of the composition of the example are also excellent. From these results, it was confirmed that the composition of the present invention can form a cured product showing a high refractive index and has excellent film-forming property.

Claims

1. A composition comprising: Compound A having at least one thiirane group or thietanyl group, a compound B having at least one (meth)acryloyl group, and Basic catalyst C, The compound B includes a compound having at least one (meth)acryloyl group and a urethane bond in the molecule.

2. The composition according to claim 1, wherein The compound B is a compound having at least one (meth)acryloyl group and having no acidic functional group.

3. The composition according to claim 1, wherein A polymerization inhibitor D is further contained.

4. The composition according to claim 1, wherein The compound A is a compound represented by formula (A-1), In formula (A-1), L represents a single bond or a divalent group, and the two Ls may be the same or different. A 1 Represents an oxygen atom or a sulfur atom, two A 1 They can be the same or different, but two A 1 At least one of is a sulfur atom, m represents 0 or 1, and two m can be the same or different. n represents any integer from 0 to 6, R 1 represents a monovalent substituent. When R 1 When multiple, multiple R 1 Can be the same or different, R 2 represents a hydrogen atom or a monovalent substituent, and the two R 2 Can be the same or different.

5. A molded article obtained by curing the composition according to any one of claims 1 to 4. 6 . A cured product, which is a cured product of the composition according to claim 1 .

7. A display device comprising the cured product according to claim 6.

8. A solid-state imaging device comprising the cured product according to claim 6.

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