Compound and method for producing the same, composition, cured product, display device, solid-state imaging element, sealing material and insulating material

Abstract

To provide a novel compound capable of providing a cured product having excellent lithographic performance and a high refractive index, and a method for producing the same.SOLUTION: There is provided a compound represented by the formula (I).[In the formula (I), L represents a single bond or a divalent group and a plurality of Ls may be the same or different. A represents an oxygen atom or a sulfur atom and a plurality of As may be the same or different. n represents any integer from 0 to 6. R represents a monovalent substituent and when there are a plurality of Rs, the plurality of Rs may be the same or different. R2 represents a hydrogen atom or a monovalent substituent and a plurality of R2s may be the same or different.]SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a compound and a method for producing the same, a composition, a cured product, a display device, a solid-state imaging device, a sealing material, and an insulating material. [Background technology]

[0002] In the field of optical instruments, there is a demand for highly refractive materials. Highly refractive materials can be used to obtain lenses, which can control the optical path in optical instruments. Lenses are used in solid-state imaging devices to improve the light collection efficiency for each photoelectric conversion element, and lenses are used in display devices to improve the light extraction efficiency from pixels. Various highly refractive materials have been developed in the past (for example, Patent Document 1). [Prior art documents] [Patent documents]

[0003] [Patent Document 1] International Publication No. 2011 / 102258 Summary of the Invention [Problem to be solved by the invention]

[0004] An object of the present invention is to provide a novel compound capable of giving a cured product having excellent lithography performance and a high refractive index, and a method for producing the same. Another object of the present invention is to provide a composition containing the compound, a cured product of the compound or the composition, a display device containing the cured product, a solid-state imaging device containing the cured product, and an encapsulating material and an insulating material containing the composition. [Means for solving the problem]

[0005] The present invention includes the following. [1] A compound represented by formula (I). [ka] [In formula (I), L represents a single bond or a divalent group, and multiple L's may be the same or different. A represents an oxygen atom or a sulfur atom, and a plurality of As may be the same or different. n represents an integer of 0 to 6. R represents a monovalent substituent, and when there are multiple R, the multiple R may be the same or different. R 2 represents a hydrogen atom or a monovalent substituent, and a plurality of R 2 may be the same or different.] A composition comprising the compound according to [2] [1]. [3] The composition according to [2], further comprising a polymerization initiator. [4] The composition according to claim 3, wherein the polymerization initiator is a thermal cationic polymerization initiator or a thermal anionic polymerization initiator. [5] A cured product of the compound according to [1] or the composition according to any one of [2] to [4]. [6] A display device comprising the cured product according to [5]. [7] A solid-state imaging device comprising the cured product according to [5]. [8] An encapsulating material comprising the compound according to [1] or the composition according to any one of [2] to [4]. [9] An insulating material comprising the compound according to [1] or the composition according to any one of [2] to [4].

[10] A method for producing a compound represented by formula (IA), comprising the steps of: [ka] [In formula (IA), L represents a single bond or a divalent group, and multiple L's may be the same or different. n represents an integer of 0 to 6. R represents a monovalent substituent, and when there are multiple R, the multiple R may be the same or different. R 2 represents a hydrogen atom or a monovalent substituent, and a plurality of R 2may be the same or different.] Formula (II): [ka] [In formula (II), n and R have the same meanings as defined above.] and a compound represented by formula (III): [ka] [In formula (III), R 2 has the same meaning as above, and X represents a leaving group. and a compound represented by formula (IA) to obtain a compound represented by formula (IA).

[11] A method for producing a compound represented by formula (IB), comprising the steps of: [ka] [In formula (IB), L represents a single bond or a divalent group, and multiple L's may be the same or different. A 2 represents an oxygen atom or a sulfur atom, and there are multiple A 2 may be the same or different, provided that A 2 At least one of the groups is a sulfur atom. n represents an integer of 0 to 6. R represents a monovalent substituent, and when there are multiple R, the multiple R may be the same or different. R 2 represents a hydrogen atom or a monovalent substituent, and a plurality of R 2 may be the same or different.] Formula (IA): [ka] [In formula (IA), L, n, R, and R 2 has the same meaning as above.] with a sulfurizing agent to obtain a compound represented by formula (IB). Effect of the Invention

[0006] According to the present invention, a new compound capable of giving a cured product having excellent lithography performance and a high refractive index and a method for producing the same can be provided. Also, according to the present invention, a composition containing the compound, a cured product of the compound or the composition, a display device containing the cured product, a solid-state imaging device containing the cured product, and an encapsulating material and an insulating material containing the composition can be provided. The composition containing the compound is also excellent in terms of curability (film thickness retention). DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0007] Hereinafter, embodiments of the present invention will be described in detail, however, the present invention is not limited to the following embodiments.

[0008] In this specification, a numerical range indicated using "~" indicates a range including the numerical values ​​before and after "~" as the minimum and maximum values, respectively. In the numerical ranges described in stages in this specification, the upper limit or lower limit value described in one numerical range may be replaced with the upper limit or lower limit value of another numerical range described in stages. In addition, in the numerical ranges described in this specification, the upper limit or lower limit value of the numerical range may be replaced with a value shown in the examples.

[0009] In this specification, (meth)acrylate means acrylate or the corresponding methacrylate, and the same applies to other similar expressions such as (meth)acryloyl group, (meth)acrylic acid ester, etc.

[0010] In this specification, unless otherwise specified, the materials exemplified below may be used alone or in combination of two or more within the range of the conditions. When multiple substances corresponding to each component exist, the content of each component means the total amount of the multiple substances unless otherwise specified.

[0011] The compound according to one embodiment is a compound represented by formula (I) (hereinafter, may be referred to as "compound (I)"). Compound (I) can give a cured product that has excellent lithography performance and a high refractive index.

[0012] [ka]

[0013] In formula (I), L represents a single bond or a divalent group, and a plurality of (two) L's may be the same or different. A represents an oxygen atom or a sulfur atom, and a plurality of (two) As may be the same or different. n represents an integer of 0 to 6. R represents a monovalent substituent, and when there are multiple R, the multiple R may be the same or different. R 2 represents a hydrogen atom or a monovalent substituent, and there are multiple (two) R 2 may be the same or different.

[0014] In compound (I), the two groups represented by the following formula (X) may be bonded to any one of positions 1 to 8 of the naphthalene ring. The groups represented by formula (X) on the naphthalene ring may be bonded, for example, to any one of positions 1 to 4 and any one of positions 5 to 8 (1 to 4). The same applies to the two -SH groups in the compound represented by formula (II).

[0015] [ka]

[0016] In formula (X), L, A, and R 2 has the same meaning as above, and * indicates the bonding position.

[0017] When compound (I) has one or more monovalent substituents represented by R, the monovalent substituents represented by R may be bonded to any of the 1-8 positions of the naphthalene ring, excluding the bonding position of the group represented by formula (X).

[0018] L represents a single bond or a divalent group, and a plurality of L's may be the same or different. Examples of the divalent group represented by L include divalent aliphatic chain hydrocarbon groups which may have a substituent; divalent alicyclic hydrocarbon groups which may have a substituent; divalent aromatic hydrocarbon groups which may have a substituent; and divalent groups formed by combinations of these (e.g., aralkylene groups). The methylene group (-CH2-) contained in the divalent group can be -O-, -S-, -NR 1A -(R 1A represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.) may be substituted with -CO-, -SO2-, or -SO2-.

[0019] Examples of the divalent aliphatic chain hydrocarbon group include saturated or unsaturated aliphatic chain hydrocarbon groups. More specifically, examples include alkanediyl groups such as methylene group, ethylene group, propanediyl group, butanediyl group, pentanediyl group, hexanediyl group, heptanediyl group, octanediyl group, nonanediyl group, decanediyl group, undecanediyl group, dodecanediyl group, tridecanediyl group, tetradecanediyl group, pentadecanediyl group, hexadecanediyl group, heptadecanediyl group, octadecanediyl group, nonadecanediyl group, and eicosanediyl group. The divalent aliphatic chain hydrocarbon group may be linear or branched. The number of carbon atoms in the divalent aliphatic chain hydrocarbon group is usually 1 to 20, preferably 1 to 10, more preferably 1 to 6, even more preferably 1 to 4, and particularly preferably 1 or 2.

[0020] Examples of the substituent that the divalent aliphatic chain hydrocarbon group may have include halogen atoms such as a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom; a hydroxy group; an amino group; an acetyl group; and a cyano group.

[0021] Examples of the divalent alicyclic hydrocarbon group include saturated or unsaturated alicyclic hydrocarbon groups. More specifically, examples include monocyclic alicyclic hydrocarbon groups such as cyclopropanediyl group, cyclobutanediyl group, cyclopentanediyl group, cyclohexanediyl group, cyclooctanediyl group, cyclononanediyl group, and cyclodecanediyl group; and polycyclic alicyclic hydrocarbon groups such as bicyclo[1.1.0]butanediyl group, tricyclo[2.2.1.0]heptanediyl group, bicyclo[3.2.1]octanediyl group, bicyclo[2.2.2.]octanediyl group, adamantanediyl group, bicyclo[4.3.2]undecanediyl group, and tricyclo[5.3.1.1]dodecanediyl group. The number of carbon atoms in the divalent alicyclic hydrocarbon group is usually 3 to 20, preferably 3 to 10, more preferably 3 to 6, and even more preferably 5 or 6.

[0022] Examples of the substituent that the divalent alicyclic hydrocarbon group may have include an alkyl group having 1 to 10 carbon atoms (preferably 1 to 4 carbon atoms), such as a methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, or decyl group; a halogen atom, such as a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom; a hydroxy group; an amino group; an acetyl group; and a cyano group.

[0023] The divalent aromatic hydrocarbon group may be monocyclic or polycyclic. Examples of the divalent aromatic hydrocarbon group include a phenylene group, a naphthylene group, an anthracenediyl group, and a fluorenediyl group. The number of carbon atoms in the divalent aromatic hydrocarbon group is usually 6 to 20, and preferably 6 to 10.

[0024] Examples of the substituent that the divalent aromatic hydrocarbon group may have 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, chlorine, bromine, and iodine; hydroxy groups; amino groups; acetyl groups; and cyano groups.

[0025] In one embodiment, of the two L's present in compound (I), preferably, at least one is an alkanediyl group, more preferably, both are alkanediyl groups. In this case, the number of carbon atoms in the alkanediyl group is preferably 1 to 10, more preferably 1 to 6, even more preferably 1 to 4, particularly preferably 1 or 2. In another embodiment, of the two L's present, preferably, at least one is a single bond, more preferably, both are single bonds.

[0026] A represents an oxygen atom or a sulfur atom, and a plurality of A's may be the same or different. Preferably, at least one of the two A's is a sulfur atom, and more preferably, both are sulfur atoms. As the number of sulfur atoms as A increases, a cured product showing a higher refractive index tends to be obtained. In another embodiment, at least one of the two A's is an oxygen atom, and more preferably, both are oxygen atoms.

[0027] n represents an integer of 0 to 6. n is preferably an integer of 0 to 3, more preferably an integer of 0 to 2, further preferably 0 or 1, and particularly preferably 0.

[0028] R represents a monovalent substituent, and when there are multiple R's, the multiple R's may be the same or different, or may be the same. Examples of the monovalent substituent represented by R include monovalent hydrocarbon groups such as monovalent aliphatic chain hydrocarbon groups which may have a substituent, monovalent alicyclic hydrocarbon groups which may have a substituent, monovalent aromatic hydrocarbon groups which may have a substituent, and monovalent groups consisting of combinations thereof (e.g., aralkyl groups); hydroxy groups; and groups substituted with one or two alkyl groups having 1 to 6 carbon atoms, such as amino groups, monomethylamino groups, monoethylamino groups, dimethylamino groups, diethylamino groups, and methylethylamino groups. Examples of the heterocyclic groups include an aliphatic heterocyclic group having 4 to 20 carbon atoms, such as a pyrrolidinyl group, a pyrrolinyl group, an imidazolidinyl group, an imidazolinyl group, an oxazolinyl group, a thiazolyl group, a piperidinyl group, a morpholinyl group, a piperazinyl group, an indolyl group, an isoindolyl group, a quinolyl group, a thienyl group, a pyrrolyl group, and a furyl group, and an aromatic heterocyclic group having 3 to 20 carbon atoms; a halogen atom; a nitro group; a cyano group; a carboxy group; a sulfo group; a thiol group; a formyl group; a -SF3 group; and a -SF5 group. The methylene group (-CH2-) contained in the monovalent substituent can be -O-, -S-, -NR 1B -(R 1B represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.) may be substituted with -CO-, -SO2-, or -O2-. Examples of the group in which a methylene group (-CH2-) contained in a monovalent substituent is substituted with -O- include alkoxy groups having 1 to 12 carbon atoms, such as a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, a heptyloxy group, and an octyloxy group; and alkoxyalkyl groups, such as a methoxymethyl group, an ethoxymethyl group, and a methoxyethyl group.

[0029] Examples of the monovalent aliphatic chain hydrocarbon group include saturated or unsaturated aliphatic chain hydrocarbon groups. More specifically, 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 groups can be mentioned. The monovalent aliphatic chain hydrocarbon group may be linear or branched. The number of carbon atoms in the monovalent aliphatic chain hydrocarbon group is usually 1 to 20, preferably 1 to 10, more preferably 1 to 6, even more preferably 1 to 4, and particularly preferably 1 or 2.

[0030] Examples of the substituent that the monovalent aliphatic chain hydrocarbon group may have include halogen atoms such as a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom; a hydroxy group; an amino group; an acetyl group; and a cyano group.

[0031] 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 group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cyclooctyl group, cyclononyl group, and cyclodecyl group; and polycyclic alicyclic hydrocarbon groups such as bicyclo[1.1.0]butyl group, tricyclo[2.2.1.0]heptyl group, bicyclo[3.2.1]octyl group, bicyclo[2.2.2.]octyl group, adamantyl group, bicyclo[4.3.2]undecyl group, and tricyclo[5.3.1.1]dodecyl group. The number of carbon atoms in the monovalent alicyclic hydrocarbon group is usually 3 to 20, preferably 3 to 10, more preferably 3 to 6, and even more preferably 5 or 6.

[0032] Examples of the substituent that the monovalent alicyclic hydrocarbon group may have include alkyl groups having 1 to 10 carbon atoms (preferably 1 to 4 carbon atoms), such as a methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, and decyl group; halogen atoms such as a fluorine atom, chlorine atom, bromine atom, and iodine atom; a hydroxy group; an amino group; an acetyl group; and a cyano group.

[0033] The monovalent aromatic hydrocarbon group may be monocyclic or polycyclic. Examples of the monovalent aromatic hydrocarbon group include a phenyl group, a naphthyl group, an anthracenyl group, and a fluorenyl group. The number of carbon atoms in the monovalent aromatic hydrocarbon group is usually 6 to 20, and preferably 6 to 10.

[0034] Examples of the substituent that the monovalent aromatic hydrocarbon group may have include alkyl groups having 1 to 10 carbon atoms (preferably 1 to 4 carbon atoms), such as a methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, or decyl group; halogen atoms such as a fluorine atom, chlorine atom, bromine atom, or iodine atom; a hydroxy group; an amino group; an acetyl group; and a cyano group.

[0035] R 2 represents a hydrogen atom or a monovalent substituent, and a plurality of R 2 may be the same or different, or may be the same. 2 The monovalent substituent represented by the formula (I) can be exemplified by the same monovalent substituent represented by R. 2 is 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, even 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.

[0036] Examples of compound (I) include compounds represented by formula (Ia-1), formula (Ia-2), formula (Ib-1), formula (Ib-2), formula (Ic-1), formula (Ic-2), formula (Id-1), formula (Id-2), formula (Ie-1), formula (Ie-2), formula (If-1), and formula (If-2). In these formulas, L, A, n, R, and R 2 has the same meaning as above.

[0037] [ka]

[0038] Specific examples of compound (I) are shown below, but compound (I) is not limited to these.

[0039] [ka]

[0040] [ka]

[0041] [ka]

[0042] From the viewpoint of synthesis, the molecular weight of compound (I) is preferably 2000 or less, more preferably 1000 or less, and even more preferably 750 or less. From the viewpoint of volatility, the molecular weight of compound (I) is preferably 50 or more, more preferably 100 or more, and even more preferably 150 or more.

[0043] <Method of manufacturing compound> Compound (I) includes a compound represented by formula (IA) (hereinafter sometimes referred to as "compound (IA)") and a compound represented by formula (IB) (hereinafter sometimes referred to as "compound (IB)").

[0044] [ka]

[0045] In formula (IA), L, n, R, and R 2 has the same meaning as in formula (I) above.

[0046] [ka]

[0047] In formula (IB), L, n, R, and R 2 has the same meaning as in formula (I). 2 represents an oxygen atom or a sulfur atom, and there are multiple (two) A 2 may be the same or different, provided that A 2 At least one of the A is a sulfur atom. 2 Preferably, both are sulfur atoms.

[0048] In one embodiment, the method for producing compound (IA) includes a step of reacting a compound represented by formula (II) (hereinafter, sometimes referred to as "compound (II)") with a compound represented by formula (III) (hereinafter, sometimes referred to as "compound (III)") to obtain compound (IA).

[0049] [ka]

[0050] In formula (II), n and R have the same meanings as defined above.

[0051] [ka]

[0052] In formula (III), R 2 has the same meaning as above, and X represents a leaving group.

[0053] The reaction of compound (II) with compound (III) 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 hydrogen carbonate, potassium hydrogen carbonate, lithium hydrogen carbonate, and cesium hydrogen carbonate; metal alkoxides such as sodium methoxide, potassium methoxide, lithium methoxide, sodium ethoxide, potassium ethoxide, sodium isopropoxide, potassium isopropoxide, sodium t-butoxide, and potassium t-butoxide; and organic bases such as ammonia, methylamine, dimethylamine, trimethylamine, triethylamine, diisopropylethylamine, triisopropylamine, DBU (diazabicycloundecene), DABCO (1,4-diazabicyclo[2.2.2]octane), pyridine, 2,6-dimethylpyridine, 2,6-di-t-butylpyridine, dimethylaminopyridine, triphenylphosphine, tetramethylammonium bromide, and tetramethylammonium chloride. The amount of the base used is, for example, 0.01 to 10 mol, and preferably 0.5 to 5 mol, relative to 1 mol of compound (II).

[0054] In compound (III), examples of the leaving group represented by X include halogen atoms such as fluorine atom, chlorine atom, bromine atom, and iodine atom; alkylsulfonyl groups such as methylsulfonyl group, ethylsulfonyl group, propylsulfonyl group, butylsulfonyl group, trifluoromethylsulfonyl group, perfluoroethylsulfonyl group, perfluoropropylsulfonyl group, and perfluorobutylsulfonyl group; and arylsulfonyl groups such as phenylsulfonyl group, p-toluenesulfonyl group, p-fluorophenylsulfonyl group, and pentafluorophenylsulfonyl group. Specific examples of compound (III) include epihalohydrin compounds (wherein L is a methylene group, m is 0, and R 2is a hydrogen atom and X is a halogen atom). The amount of compound (III) used is, for example, 0.01 to 20 mol, preferably 0.5 to 15 mol, relative to 1 mol of compound (II). In this step, the reaction may be carried out using two or more kinds of compound (III).

[0055] The reaction between compound (II) and compound (III) is preferably carried out in a solvent. Examples of the solvent include water, as well as organic solvents such as ketones, aromatic hydrocarbons, halogenated aromatic hydrocarbons, aliphatic hydrocarbons, halogenated aliphatic hydrocarbons, ethers, alcohols, glymes, esters, aliphatic nitriles, sulfoxides, and amides. Examples of the organic solvent include the following solvents.

[0056] Ketones: acetone, methyl ethyl ketone, diethyl ketone, butyl methyl ketone, diisobutyl ketone, methyl isobutyl ketone, methyl isoamyl ketone, 2-heptanone, 2-octanone, cyclopentanone, cyclohexanone, etc. Aromatic hydrocarbons: benzene, toluene, xylene, mesitylene, naphthalene, anisole, nitrobenzene, aniline, tetralin, durene, etc. Halogenated aromatic hydrocarbons: chlorobenzene, dichlorobenzene, chloronaphthalene, etc. Aliphatic hydrocarbons: pentane, hexane, heptane, etc. Halogenated aliphatic hydrocarbons: dichloromethane, chloroform, 1,2-dichloroethane, tetrachloroethane, tetrachloroethylene, etc. Ethers: diethyl ether, diisopropyl ether, methyl t-butyl ether, cyclopentyl methyl ether, diphenyl ether, dimethoxyethane, dioxane, etc. Alcohols: methanol, ethanol, propanol, isopropanol, butanol, t-butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, hexafluoroisopropanol, etc. Glymes: methyl diglyme, ethyl diglyme, triglyme, diethylene glycol butyl methyl ether, etc. Esters: methyl acetate, ethyl acetate, propyl acetate, butyl acetate, etc. Aliphatic nitriles: acetonitrile, etc. Sulfoxides: dimethyl sulfoxide, sulfolane, etc. Amides: N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, etc.

[0057] The temperature for the reaction of compound (II) with compound (III) is, for example, -80 to 200°C, and preferably 0 to 150°C.

[0058] In this manner, compound (IA) can be obtained. When the obtained compound (IA) is used in the synthesis of compound (IB), compound (IA) may be used after being isolated, or may be subjected to the production method of compound (IB) without being isolated.

[0059] In one embodiment, the method for producing compound (IB) includes a step of obtaining compound (IB) by reacting compound (IA) with a sulfurizing agent. The method for producing compound (IB) may further include a step of obtaining compound (IA) by reacting compound (II) with compound (III) described above before the step of obtaining compound (IB).

[0060] The reaction of compound (IA) with a sulfurizing agent is a reaction in which an oxygen atom of an oxetanyl ring in compound (IA) is replaced with a sulfur atom using a sulfurizing agent to form a thietane ring. Examples of the sulfurizing agent include thiourea, methylthiourea, dimethylthiourea, trimethylthiourea, tetramethylthiourea, tetraethylthiourea, ethylenethiourea, phenylthiourea, diphenylthiourea, tolylthiourea, ditolylthiourea, sodium thiocyanate, and potassium thiocyanate. The amount of the sulfurizing agent used can be adjusted arbitrarily according to the oxygen atom to be replaced. The amount of the sulfurizing agent used is, for example, 0.01 to 20 moles, and preferably 0.5 to 10 moles, relative to 1 mole of compound (IA). In addition, by adjusting the amount of the sulfurizing agent used, the reaction temperature, the reaction time, and the like, both oxygen atoms in compound (IA) can be replaced with sulfur atoms, or one oxygen atom in compound (IA) can be replaced with a sulfur atom.

[0061] The reaction of compound (IA) with a sulfurizing agent is preferably carried out in a solvent. Examples of the solvent include those exemplified in the reaction of compound (II) with compound (III). The reaction of compound (IA) with a sulfurizing agent is carried out at a temperature of, for example, -80 to 200°C, preferably 0 to 100°C.

[0062] A polymerization inhibitor may be added to the reaction system to inhibit polymerization of the produced compound (IB). Examples of the polymerization inhibitor include acids and acid anhydrides. More specifically, Inorganic acidic compounds such as nitric acid, hydrochloric acid, perchloric acid, hypochlorous acid, chlorine dioxide, hydrofluoric acid, sulfuric acid, oleum, sulfuryl 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, anhydrous nitric acid, anhydrous sulfuric acid, boron oxide, arsenic pentoxide, phosphorus pentoxide, anhydrous chromic acid, silica, alumina, 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, and cesium dihydrogen phosphate; 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, acetic acid, 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, salicylic acid, benzilic acid, α-naphthalenecarboxylic acid, β-naphthalenecarboxylic acid, acetic anhydride, propionic anhydride, butyric anhydride, succinic anhydride, maleic anhydride, benzoic anhydride, phthalic anhydride, pyromellitic anhydride, trimellitic anhydride, and trifluoroacetic anhydride; phosphoric acids such as mono-, di-, and trimethyl phosphate, mono-, di-, and triethyl phosphate, mono-, di-, and triisobutyl phosphate, mono-, di-, and tributyl phosphate, and mono-, di-, and trilauryl phosphate, and phosphorous acids in which the phosphate moiety is converted into a phosphite; Organophosphorus compounds such as dialkyldithiophosphates, typified by dimethyldithiophosphate; Phenols such as phenol, catechol, t-butylcatechol, 2,6-di-t-butylcresol, 2,6-di-t-butylethylphenol, resorcinol, hydroquinone, phloroglucinone, pyrogallol, cresol, ethylphenol, butylphenol, nonylphenol, hydroxyphenylacetic acid, hydroxyphenylpropionic acid, hydroxyphenylacetic acid amide, methyl hydroxyphenylacetate, ethyl hydroxyphenylacetate, hydroxyphenethyl alcohol, hydroxyphenethylamine, hydroxybenzaldehyde, phenylphenol, bisphenol-A, 2,2'-methylene-bis(4-methyl-6-t-butylphenol), bisphenol-F, bisphenol-S, α-naphthol, β-naphthol, aminophenol, chlorophenol, and 2,4,6-trichlorophenol; 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-cresolsulfonic acid, metanilic acid, sulfanilic acid, 4B-acid, diaminostilbenesulfonic acid, biphenylsulfonic acid, α-naphthalenesulfonic acid, β-naphthalenesulfonic acid, peric acid, Laurent acid, and phenyl J acid. etc.

[0063] The amount of the polymerization inhibitor used is, for example, 0.0001 to 1.0 mol, and preferably 0.01 to 0.2 mol, relative to 1 mol of compound (IB). 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.

[0064] The reaction product solution can be washed with an acidic aqueous solution to improve the stability over time of the compound (IB). Specific examples of acids used in the acidic aqueous solution include nitric acid, hydrochloric acid, sulfuric acid, boric acid, arsenic acid, phosphoric acid, hydrocyanic acid, acetic acid, chloroacetic acid, dichloroacetic acid, trichloroacetic acid, trifluoroacetic acid, peracetic acid, thioacetic acid, oxalic acid, tartaric acid, succinic acid, and maleic acid. Aqueous solutions of these acids usually tend to be effective at pH 6 or less, but a more effective range is pH 3 or less. The acid used in the acidic aqueous solution is preferably hydrochloric acid, sulfuric acid, phosphoric acid, or maleic acid.

[0065] Furthermore, a hydrogen sulfide adsorbent can be used to improve the stability of compound (IB). Examples of hydrogen sulfide adsorbents include iron (III) hydroxide, zinc oxide, KNK-301 (zinc oxide adsorbent, manufactured by Kureha Yushi Kogyo Co., Ltd.), Nionon 202A (iron oxide adsorbent, manufactured by Ibuki Seisakusho Co., Ltd.), and Limonic (iron hydroxide, manufactured by Nippon Limonite Co., Ltd.). The hydrogen sulfide adsorbent can be added during the reaction, or can be added and used in purification after the reaction.

[0066] <Composition> The composition of one embodiment includes compound (I). In addition to compound (I), the composition may further include other components other than compound (I). Since compound (I) tends to be easily cured, the composition can be cured by irradiation with active energy rays or heating. By curing the composition, a molded product containing a cured product of the composition can be formed. Here, the molded product means a product containing a cured product of the composition and molded into a desired shape.

[0067] The content of compound (I) in the composition is preferably 1 mass% or more, more preferably 5 mass% or more, even more preferably 10 mass% or more, particularly preferably 20 mass% or more, and most preferably 30 mass% or more, relative to the total amount of solids in the composition, and is preferably 100 mass% or less, more preferably 99 mass% or less, even more preferably 95 mass% or less, particularly preferably 90 mass% or less, and most preferably 85 mass% or less.

[0068] The total amount of solids in the composition means the total amount of the components contained in the composition excluding the solvent. The content of each component in the solids of the composition can be measured by known analytical means such as liquid chromatography and gas chromatography. The content of each component in the solids of the composition may be calculated from the blending at the time of preparing the composition.

[0069] Examples of other components contained in the composition include a resin, a curable compound other than Compound (I), a polymerization initiator, a solvent, an additive, etc. Examples of additives include inorganic particles, a filler, a polymerization initiator assistant, a sensitizer, a leveling agent, a stabilizer, a surfactant, an antistatic agent, a lubricant, an antifouling agent, an ultraviolet absorber, an antioxidant, a dispersant, etc.

[0070] (1) Resin The composition may contain one or more resins. By containing a resin in the composition, it is possible to impart developability to a cured product of the composition, and to adjust the mechanical properties and / or optical properties of the cured product and a molded product containing the cured product. Examples of the resin include thermoplastic resins and curable resins. The curable resin may be a photocurable resin that is cured by irradiation with active energy rays, or a thermosetting resin that is cured by heat.

[0071] Examples of the thermoplastic resin include olefin resins such as polyethylene resin, polypropylene resin, and polycycloolefin resin; (meth)acrylic resins such as poly(meth)acrylic acid ester resin; styrene resins such as polystyrene resin, styrene-acrylonitrile resin, and acrylonitrile-butadiene-styrene resin; vinyl resins such as polyvinyl chloride resin, polyvinylidene 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; polyacetal resin; polyamide resin; polycarbonate resin; polyurethane resin; polyphenylene sulfide resin, etc. One or more of these resins may be used as a polymer blend or polymer alloy.

[0072] Examples of the curable resin include resins having a photopolymerizable group or a thermally polymerizable group, more specifically, (meth)acrylic resins, epoxy resins, melamine resins, unsaturated polyester resins, phenolic resins, urea resins, alkyd resins, polyimide resins, etc.

[0073] Other examples of the resin include an alkali-soluble resin. By including an alkali-soluble resin in the composition, it is possible to impart developability to the cured product of the composition. The alkali-soluble resin means a resin that is soluble in an alkaline aqueous solution. Specifically, for example, a resin having a carboxyl group and / or a phenolic hydroxyl group can be mentioned.

[0074] 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 determined, for example, by titration with an aqueous potassium hydroxide solution.

[0075] Another example of the resin is a high refractive index resin, which means a resin having a refractive index of 1.60 or more at a wavelength of 550 nm.

[0076] The weight average molecular weight (Mw) of the resin, calculated based on standard polystyrene, measured by gel permeation chromatography (GPC) is, for example, 5 to 2 million, preferably 1,000 to 1 million, and more preferably 1,500 to 750,000. The Mw of the resin can be adjusted by appropriately combining reaction conditions such as the selection of raw materials used, the charging method, the reaction temperature, and the reaction time.

[0077] When the composition contains a resin, the content of the resin in the composition is preferably 5% by mass or more, more preferably 10% by mass or more, and preferably 80% by mass or less, more preferably 70% by mass or less, based on the total amount of solids in the composition.

[0078] (2) Curable compounds other than compound (I) The composition may contain one or more curable compounds other than the compound (I). By containing a curable compound other than the compound (I), the viscosity or curability of the composition can be adjusted, and the mechanical properties and / or optical properties of the obtained cured product and a molded product containing the same can be adjusted.

[0079] Examples of the curable compound other than compound (I) include episulfide compounds, epoxy compounds, oxetane compounds other than compound (I), thietane compounds other than compound (I), hydroxy compounds, carboxy compounds, vinyl ether compounds, allyl compounds, thiol compounds, polyphenol compounds, iso(thio)cyanate compounds, (meth)acrylate compounds, and acid anhydrides.

[0080] When the composition contains a curable compound other than compound (I), the content of the curable compound in the composition is preferably 1 mass % or more, more preferably 2 mass % or more, and preferably 30 mass % or less, more preferably 20 mass % or less, based on the total amount of solids in the composition.

[0081] (3) Polymerization initiator The composition may contain one or more polymerization initiators. The polymerization initiator is not particularly limited as long as it can initiate the polymerization of the compound (I), and examples thereof include radical polymerization initiators, cationic polymerization initiators, anionic polymerization initiators, radical and cationic polymerization initiators, etc. These polymerization initiators generate radicals, acids, or bases by at least one of irradiation with active energy rays and heat, and promote radical polymerization, cationic polymerization, or anionic polymerization of the compound (I). The compound (I) can be polymerized and cured by at least one of irradiation with active energy rays and heat even in the absence of a polymerization initiator.

[0082] Examples of radical polymerization initiators that initiate radical polymerization by heat include organic peroxides such as hydrogen peroxide and perbenzoic acid, and azo compounds such as azobisbutyronitrile. Examples of photoradical polymerization initiators that initiate radical polymerization by irradiation with active energy rays include oxime compounds, alkylphenone compounds, arylketone compounds, biimidazole compounds, triazine compounds, and acylphosphine compounds.

[0083] A cationic polymerization initiator is a compound capable of releasing a substance that initiates cationic polymerization by at least one of irradiation with active energy rays and heat. Examples of cationic polymerization initiators include iodonium salts, sulfonium salts, ammonium salts, and cyclopentadienyl iron (II) complexes. These can initiate cationic polymerization by at least one of irradiation with active energy rays and heat depending on the difference in structure. A compound capable of releasing a substance that initiates cationic polymerization by irradiation with active energy rays is called a photo-cationic polymerization initiator, and a compound capable of releasing a substance that initiates cationic polymerization by heat is called a thermal cationic polymerization initiator.

[0084] An anionic polymerization initiator is a compound capable of releasing a substance that initiates anionic polymerization by at least one of irradiation with active energy rays and heat. Examples of anionic polymerization initiators include ammonium salts, DBU (diazabicycloundecenium) salts, DBN (diazabicyclononenium) salts, biguanidium salts, aromatic phosphonium salts, aromatic dimethylurea, and aliphatic dimethylurea. These can initiate anionic polymerization by at least one of irradiation with active energy rays and heat depending on the difference in structure. A compound capable of releasing a substance that initiates anionic polymerization by irradiation with active energy rays is called a photoanionic polymerization initiator, and a compound capable of releasing a substance that initiates anionic polymerization by heat is called a thermal anionic polymerization initiator.

[0085] When the composition contains a polymerization initiator, from the viewpoint of improving the heat resistance of the composition and a cured product thereof, the composition preferably contains a thermal cationic polymerization initiator or a thermal anionic polymerization initiator, more preferably a thermal anionic polymerization initiator, while from the viewpoint of improving the lithography performance, the composition preferably contains a photocationic polymerization initiator.

[0086] When the composition contains a polymerization initiator, the content of the polymerization initiator in the composition is, relative to 100 parts by mass in total of compound (I) and other curable compounds, preferably 0.1 parts by mass or more, and more preferably 0.5 parts by mass or more, from the viewpoint of enhancing curability, and is preferably 10 parts by mass or less, and more preferably 8 parts by mass or less, from the viewpoint of improving physical properties such as the mechanical properties of the cured product.

[0087] (4) Solvent The composition may contain one or more solvents. The solvent is preferably one that can dissolve or disperse compound (I), and more preferably one that can further dissolve or disperse other components other than compound (I). Examples of the solvent include the solvents exemplified in the reaction between compound (II) and compound (III). Examples of the solvent other than these solvents (organic solvents) include ether esters such as methyl methoxyacetate, ethyl methoxyacetate, methyl 3-methoxypropionate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, and ethylene glycol monomethyl ether acetate.

[0088] When the composition contains a solvent, the content of the solvent in the composition is preferably 60 parts by mass or more, more preferably 80 parts by mass or more, and preferably 1000 parts by mass or less, more preferably 500 parts by mass or less, relative to 100 parts by mass of the solid content of the composition. When the composition contains a solvent, the solid content concentration of the composition is preferably 5 to 60% by mass, more preferably 10 to 50% by mass.

[0089] <Cured products and molded products> The cured product of one embodiment is a cured product of the compound (I) or a cured product of the composition. The molded product of one embodiment includes a cured product. Since the compound (I) and the composition have excellent film-forming and curing properties, they can be suitably used as a curable material for producing a cured product or a molded product containing the same. The cured product can be obtained by curing the compound (I) or the composition by 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 may include a film (membrane), plate, lens, powder, granule, non-spherical particle, crushed particle, porous, chunky continuous body, fiber, tube, hollow fiber, etc., and may be any shape depending on the application of the molded product.

[0090] The method for obtaining a molded product from the composition is not particularly limited, and examples thereof include a method in which a film is formed on a substrate and then shaped by etching or the like, an injection molding method, and a cast polymerization molding method.

[0091] In the cast polymerization molding method, for example, compound (I) or the composition is injected into a mold, degassed as necessary, cured by heating in an oven, etc., and the obtained molded product is taken out. The molded product taken out can also be irradiated with active energy rays for additional curing.

[0092] When forming a film as a molded product on a substrate, the compound (I) or composition is applied to the substrate, and dried as necessary to form a coating film (coating layer), and the coating film (coating layer) is cured to obtain a molded product that is a cured film (cured layer). The molded product may be a patterned cured film (cured layer). The patterned cured film can be obtained by patterning using a method such as a photolithography method, an inkjet method, or a printing method. The patterning method may be, for example, a photolithography method. The photolithography method is a method in which the compound (I) or composition is applied to a substrate, and dried as necessary to form a coating film (coating layer), the coating film (coating layer) is exposed through a photomask, and the coating film (coating layer) after exposure is developed.

[0093] Examples of the substrate include glass plates such as quartz glass, borosilicate glass, alumina silicate glass, soda lime glass with a silica-coated surface, and alkali-free glass; resin plates such as polycarbonate, polymethyl methacrylate, and polyethylene terephthalate; silicon; and substrates having aluminum, silver, and silver / copper / palladium alloy thin films formed thereon. Methods for applying the compound (I) or the composition to the substrate include spin coating, slit coating, and slit and spin coating.

[0094] The light source used for exposure is preferably a light source that generates light with a wavelength of 250 to 450 nm. For example, from light with wavelengths in this range, light with wavelengths around 436 nm, around 408 nm, or around 365 nm may be selectively extracted by a bandpass filter according to the absorption wavelength of the photopolymerization initiator. Specific examples of the light source include a mercury lamp, a light-emitting diode, a metal halide lamp, and a halogen lamp. After the pattern exposure, the exposed coating film (coating layer) may be heated before development (pre-development bake).

[0095] Examples of the developer used for development include aqueous solutions and solvents containing alkaline compounds such as potassium hydroxide, sodium bicarbonate, sodium carbonate, and tetramethylammonium hydroxide (TMAH). Examples of the solvent include the solvents (organic solvents) exemplified in the reaction between compound (II) and compound (III). The developer may contain a surfactant. Examples of the development method include a puddle method, a dipping method, and a spray method. The patterned cured film (cured layer) obtained by development may be further heated (post-baked).

[0096] The cured product or a molded product containing the same is formed from compound (I) or a composition containing the same, and therefore can exhibit a high refractive index, and the refractive index can be controlled to a desired refractive index by adjusting the composition of the composition. The refractive index of the cured product or a molded product containing the same at a wavelength of 550 nm may be 1.60 or more, 1.65 or more, 1.70 or more, or 1.72 or more. The refractive index of the cured product or a molded product containing the same at a wavelength of 550 nm may be, for example, 1.80 or less, or 1.78 or less.

[0097] The refractive index at a wavelength of 550 nm of the cured product or a molded product containing the same 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 on which a cured film is formed. Next, a transmission spectrum and a reflection spectrum at wavelengths of 300 nm to 800 nm are measured for the substrate on which the cured film is formed using a visible-ultraviolet spectrophotometer (e.g., "V-650" manufactured by JASCO Corporation) equipped with an integrating sphere unit (e.g., "ISV-922" manufactured by JASCO Corporation). Next, from the true reflection spectrum obtained by subtracting the increase or decrease due to interference in the reflection spectrum from the transmission spectrum and the reflection spectrum and smoothing it, the refractive index at a wavelength of 550 nm of the cured product or a molded product containing the same is calculated based on the Fresnel formula (e.g., Hecht Optics I Original 5th Edition, Maruzen Publishing, 2018, p.209-226). This allows the refractive index at a wavelength of 550 nm of the cured product or a molded product containing the same to be obtained.

[0098] <Usage> Applications of the cured or molded products include, for example, glass substitutes and surface coating materials thereof; coating materials for window glass, lighting glass, and light source protection glass for residences, facilities, transportation equipment, etc.; window films for residences, facilities, transportation equipment, etc.; interior and exterior materials and interior and exterior paints for residences, facilities, transportation equipment, etc., and coating films formed by such paints; alkyd resin lacquer paints and coating films formed by such paints; acrylic lacquer paints and coating films formed by such paints; components for light sources that emit ultraviolet rays, such as fluorescent lamps and mercury lamps; components for precision machinery, electronic and electrical equipment, and materials for blocking electromagnetic waves generated by various displays; containers or packaging materials for food, chemicals, pharmaceuticals, etc.; bottles, boxes, blisters, cups, special packaging, compact disc coatings, agricultural and industrial sheets or films; anti-fading agents for printed matter, dyed matter, dyes and pigments, etc.; protective films for polymer supports (for example, for plastic parts of machines and automobile parts); printing overcoats; inkjet media coatings; matte laminates; optical light films; safety glass / windshield interlayers; electrochromic / photochromic applications; overlaminate films; solar heat control films; cosmetics such as sunscreen creams, shampoos, conditioners, hair products, etc.; clothing textiles and fibers such as sportswear, stockings, hats, etc.; household interior items such as curtains, carpets, wallpaper, etc.; medical devices such as plastic lenses, contact lenses, artificial eyes, etc.; optical products such as optical filters, backlight display films, prisms, lenses (e.g., eyeglass lenses, camera lenses, and microlenses and pickup lenses described below), mirrors, photographic materials, etc.; stationery such as mold films, transfer stickers, anti-graffiti films, tapes, inks, etc.; sign boards, markers, etc. and their surface coating materials; substrates used in optical devices, etc.; optical waveguides; holograms; LED encapsulants, etc.

[0099] The molded article is suitably used as a lens, which is an optical component used in an optical device. Examples of the optical device include a solid-state imaging element and a display device. In a solid-state imaging element, a lens is used for improving the efficiency of collecting light on each photoelectric conversion element. In a display device, a lens is used for improving the efficiency of extracting light from a pixel. The lens may be a microlens. Examples of the display device include a liquid crystal display device and an organic EL display device.

[0100] Conventionally, inorganic compounds such as zirconium oxide and titanium oxide have been known as high refractive index materials. However, when producing a molded product containing a high refractive index material made of an inorganic compound, it may not be easy to mold the product because etching is difficult to proceed, and the high refractive index material may scatter during molding, causing contamination problems. Such problems can be solved by using the high refractive index material of the present embodiment, which is an organic compound.

[0101] The compound (I) and the composition of the present embodiment can be applied to an encapsulating material. The encapsulating material of one embodiment includes the compound (I) or the composition. The encapsulating material of the present embodiment can have excellent lithography performance. The encapsulating material of the present embodiment can form a cured product or a molded product thereof having a small coefficient of linear thermal expansion (CTE). The encapsulating material of the present embodiment can also form a cured product or a molded product thereof having low water absorption and high flexibility. The cured product or the molded product can be used as various encapsulating members such as LED encapsulating members and semiconductor encapsulating members. The encapsulating member may be an encapsulating film.

[0102] The sealing material of the present embodiment may further contain other components in addition to the compound (I) or the composition. Examples of the other components include an inorganic filler. The content of the inorganic filler may be, for example, 0.5 to 10,000 parts by mass with respect to 100 parts by mass of the compound (I) or the composition.

[0103] The compound (I) and composition of this embodiment can be applied to an insulating material. An insulating material of one embodiment includes the compound (I) or the composition. The insulating material of this embodiment can have excellent lithography performance. The insulating material of this embodiment can form a cured product or a molded product thereof having excellent dielectric constant and dielectric loss tangent. In addition, the insulating material of this embodiment can form a cured product or a molded product thereof having a small coefficient of linear thermal expansion (CTE). The cured product or the molded product can be used as various insulating members. The insulating member may be an interlayer insulating film.

[0104] The insulating material of the present embodiment may further contain other components in addition to the compound (I) or the composition, such as a plasticizer, an antioxidant, a heat stabilizer, and an antistatic agent. EXAMPLES

[0105] The present invention will be described in more detail below with reference to examples. However, the present invention is not limited to these examples. In the following, "parts" means "parts by mass" unless otherwise specified.

[0106] [Example 1-1: Synthesis of compound represented by formula (Ia-1-1)] A four-neck flask equipped with a Dimroth condenser and a thermometer was filled with nitrogen, and 5 parts of the compound represented by formula (IIa-1) (1,6-naphthalenedithiol), 20 parts of N,N-dimethylformamide, 11.9 parts of the compound represented by formula (IIIa-1) (3-oxetanyl p-toluenesulfonate), and 42.4 parts of cesium carbonate were added to the flask and stirred for 7 hours at 60° C. The resulting mixture was purified to obtain 2.5 parts of the compound represented by formula (Ia-1-1).

[0107] [ka]

[0108] LC-MS measurement and 1 H-NMR analysis confirmed that the compound represented by formula (Ia-1-1) was produced. 1 H-NMR (deuterated chloroform) δ: 8.22-8.24 (1H), 7.56-7.64 (2H), 7.36-7.39 (2H), 7.28-7.30 (1H), 4.99-5.10 (4H), 4.65-4.72 (4H), 4.44-4.62 (2H) LC-MS: [M+H] + =305.5

[0109] [Example 1-2: Synthesis of compound represented by formula (Ia-1-1)] A four-neck flask equipped with a Dimroth condenser and a thermometer was filled with nitrogen, and 0.4 parts of the compound represented by formula (IIa-1) (1,6-naphthalenedithiol), 4 parts of dimethyl sulfoxide, 0.7 parts of the compound represented by formula (IIIa-2) (3-bromooxetane), and 1.7 parts of cesium carbonate were added to the flask and stirred for 7 hours at 60° C. The resulting mixture was purified to obtain 0.3 parts of the compound represented by formula (Ia-1-1).

[0110] [ka]

[0111] LC-MS measurement and 1 H-NMR analysis showed the same results as in Example 1, confirming that the compound represented by formula (Ia-1-1) was produced.

[0112] [Example 1-3: Synthesis of compound represented by formula (Ia-1-2)] A four-neck flask equipped with a Dimroth condenser and a thermometer was filled with nitrogen, and 5 parts of the compound represented by formula (IIa-1) (1,6-naphthalenedithiol), 25 parts of acetone, and 7.8 parts of the compound represented by formula (IIIa-3) were added to the flask and stirred at 25°C for 10 minutes. Then, 2.6 parts of sodium hydroxide and 25 parts of pure water were added to another flask and completely dissolved, and then added to the four-neck flask. After the addition, the temperature was raised to 65°C and stirred at 65°C for 2 hours. The resulting mixture was purified to obtain 6 parts of the compound represented by formula (Ia-1-2).

[0113] [ka]

[0114] LC-MS measurement and 1 H-NMR analysis confirmed that the compound represented by formula (Ia-1-2) was produced. 1 H-NMR (deuterated chloroform) δ: 8.32-8.34 (1H), 7.77-7.78 (1H), 7.52-7.59 (3H), 7.37-7.41 (1H), 4.35-4.53 (8H), 3.29-3.38 (4H), 1.44-1.47 (6H) LC-MS: [M+H] + =361.5

[0115] [Synthesis Example: Synthesis of Compound Represented by Formula (X-1)] A four-neck flask equipped with a Dimroth condenser and a thermometer was filled with nitrogen, and 23.5 parts of the compound represented by formula (IIa-1) (1,6-naphthalenedithiol), 117.5 parts of acetone, and 25.4 parts of chloroacetic acid were added to the flask and stirred in an ice bath for 10 minutes. Then, 19.6 parts of sodium hydroxide and 117.5 parts of pure water were added to another flask and completely dissolved, and then added to the four-neck flask. After addition, the temperature was raised to 25°C and stirred at 25°C for 3 hours. The resulting mixture was purified to obtain 30 parts of the compound represented by formula (X-1).

[0116] [ka]

[0117] [Example 2-1: Preparation of composition] 100 parts by mass of the compound represented by formula (Ia-1-1) obtained in Example 1-1 or Example 1-2, 5 parts by mass of polymerization initiator A, and 250 parts by mass of cyclopentanone as a solvent were placed in a flask and stirred to obtain a liquid composition. The obtained composition was visually observed to be transparent, and it was confirmed that the blended components were uniformly dissolved.

[0118] [Example 2-2: Preparation of composition] A liquid composition was obtained in the same manner as in Example 2-1, except that 100 parts by mass of the compound represented by formula (Ia-1-1) was replaced with 100 parts by mass of the compound represented by formula (Ia-1-2) obtained in Example 1-3. The obtained composition was visually observed to be transparent, and it was confirmed that the blended components were uniformly dissolved.

[0119] [Comparative Examples 2-1 and 2-2: Preparation of Compositions] Liquid compositions were obtained in the same manner as in Example 2-1, except that the types of ingredients in the compositions and the amounts of those ingredients added were changed as shown in Table 1. The compositions of Comparative Examples 2-1 and 2-2 were transparent when visually observed, and it was confirmed that the ingredients were uniformly dissolved.

[0120] The details of the abbreviations of the ingredients shown in Table 1 are as follows. [1] (Ia-1-1): Compound represented by formula (Ia-1-1) (Example 1-1 or Example 1-2) [2] (Ia-1-2): Compound represented by formula (Ia-1-2) (Example 1-3) [3] (X1): Compound represented by formula (X-1) (Synthesis example) [4] (Y1): Compound represented by formula (Y1) (synthesized according to the description of Example 6 of WO 2023 / 058449) [ka] [5] (Y2): A compound represented by formula (Y2) (bisphenol A diglycidyl ether, manufactured by DIC Corporation, "EPICLON EXA-850CRP") [ka] [6] Polymerization initiator A: Ammonium salt type thermal cationic polymerization initiator (KING INDUSTRIES INC., "CXC-1821")

[0121] [Evaluation test] (1) Refractive index of the cured product (1-1) Formation of Cured Film (Formation of Cured Film Using Compositions of Examples 2-1 and 2-2, and Comparative Examples 2-1 and 2-2) About 3 mL of the compositions prepared in Examples 2-1 and 2-2 and Comparative Examples 2-1 and 2-2 were dropped onto alkali-free glass (thickness 0.7 mm, Corning Incorporated, "Eagle XG") and spin-coated at 1000 rpm for 20 seconds using a spin coater (Mikasa Co., Ltd., "MS-B100") to form a coating film. The alkali-free glass plate on which the coating film was formed was heated at 60°C for 2 minutes as pre-baking. Next, the alkali-free glass plate on which the coating film was formed was exposed to 1000 mJ / cm2 in air using a high-pressure mercury lamp proximity UV exposure device (Ushio Inc., "UV-3300SC"). 2 The non-alkali glass plate on which the exposed coating film was formed was then post-baked at 120°C for 5 minutes to obtain a non-alkali glass plate on which a cured film was formed. The thickness of the cured film on the non-alkali glass was measured with a stylus film thickness meter (Bruker's "DekTak XT") and found to be 1.5 μm. The curing conditions for the coating film are summarized in Table 1.

[0122] (1-2) Refractive index measurement The non-alkali glass plate on which the cured film was formed, prepared in (1-1), was measured for the transmission spectrum and reflection spectrum at wavelengths of 300 nm to 800 nm using a visible-ultraviolet spectrophotometer (manufactured by JASCO Corporation, "V-650") with an integrating sphere unit (manufactured by JASCO Corporation, "ISV-922"). The true reflection spectrum obtained by subtracting the increase or decrease due to interference in the reflection spectrum from the transmission spectrum and reflection spectrum and smoothing it was calculated from the value at a wavelength of 550 nm and the refractive index of the non-alkali glass (manufactured by Corning, "Eagle XG") based on the Fresnel formula (Hecht Optics I Original 5th Edition, Maruzen Publishing, 2018, p.209-p.226). The results are shown in Table 1.

[0123] (2) Curability (film thickness retention rate) In the same manner as in (1-1), alkali-free glasses each having a cured film formed thereon were obtained using the compositions of Examples 2-1 and 2-2 and Comparative Examples 2-1 and 2-2.

[0124] The curability (thickness retention) of the composition was evaluated for the obtained cured film of the alkali-free glass according to the following evaluation criteria. The curability was evaluated by immersing the alkali-free glass on which the cured film was formed in acetone at 23°C for 10 minutes, and measuring the change in appearance of the cured film before and after immersion and the thickness retention before and after immersion (thickness retention = thickness of the cured film after immersion / thickness of the cured film before immersion x 100 (%)). If the result is A or B, it can be said that the curability is good. A: There was no change in appearance, and the film thickness retention was 90% or more but not exceeding 100%. B: There was no change in appearance, and the film thickness retention was less than 90% and 80% or more. C: There was no change in appearance, and the film thickness retention was less than 80%. D: Regardless of the film thickness retention rate, the cured film became cloudy after immersion.

[0125] [Table 1]

[0126] [Example 3-1: Preparation of composition] 80 parts by mass of the compound represented by formula (Ia-1-1) obtained in Example 1-1 or Example 1-2, 20 parts by mass of the compound represented by formula (X-1), 5 parts by mass of polymerization initiator A, and 250 parts by mass of cyclopentanone as a solvent were placed in a flask and stirred to obtain a liquid composition. The obtained composition was visually transparent, and it was confirmed that the blended components were uniformly dissolved.

[0127] [Example 3-2: Preparation of composition] A liquid composition was obtained in the same manner as in Example 3-1, except that 80 parts by mass of the compound represented by formula (Ia-1-1) was replaced with 80 parts by mass of the compound represented by formula (Ia-1-2) obtained in Example 1-3. The obtained composition was visually observed to be transparent, and it was confirmed that the blended components were uniformly dissolved.

[0128] [Comparative Examples 3-1 and 3-2: Preparation of Compositions] Liquid compositions were obtained in the same manner as in Example 3-1, except that the types of ingredients in the compositions and the amounts of those ingredients added were changed as shown in Table 2. The compositions of Comparative Examples 3-1 and 3-2 were transparent when visually observed, and it was confirmed that the ingredients were uniformly dissolved.

[0129] [Evaluation test] (3) Lithography performance About 3 mL of the compositions prepared in Examples 2-1 and 2-2 and Comparative Examples 2-1 and 2-2 were dropped onto alkali-free glass (thickness 0.7 mm, Corning Incorporated, "Eagle XG") and spin-coated at 1000 rpm for 20 seconds using a spin coater (Mikasa Co., Ltd., "MS-B100") to form a coating film. The alkali-free glass plate on which the coating film was formed was heated at 80°C for 2 minutes. Next, the alkali-free glass plate on which the coating film was formed was exposed to 1000 mJ / cm2 in air using a high-pressure mercury lamp proximity UV exposure device (Ushio Inc., "UV-3300SC"). 2 Proximity exposure was performed through a photomask with an irradiation energy of 1000 μm, with a gap of 200 μm between the photomask and the coating surface. The non-alkali glass plate on which the coating film was formed after exposure was then heated at 80° C. for 2 minutes, immersed in a 2.38% by mass aqueous solution of TMAH for 1 minute, and then immersed in pure water for 1 minute for development. The non-alkali glass on which a patterned cured film was formed was then obtained by heating at 120° C. for 5 minutes using a hot plate. The thickness of the non-patterned portion of the cured film on the non-alkali glass was measured using a stylus film thickness meter (DekTak XT, manufactured by Bruker) and found to be 1.5 μm.

[0130] The lithography performance of the obtained cured film was evaluated according to the following evaluation criteria. The lithography performance was evaluated by observing the cross section of a 5 μm wide, one-to-one line and space pattern and using the top loss rate (= (difference in thickness between non-patterned portion and patterned portion) ÷ (thickness of non-patterned portion) × 100 (%)). The results are shown in Table 2. The smaller the top loss rate, i.e., the closer to 0%, the better the lithography performance. A: The top loss rate was between 0% and 10%. B: The top loss rate was greater than 10% and less than 20%. C: The top loss rate was higher than 20% and less than 40%.

[0131] [Table 2]

[0132] As shown in Tables 1 and 2, the compositions of the examples were superior to the compositions of the comparative examples in terms of both the refractive index and lithography performance of the cured product. It was also found that the compositions of the examples were superior in terms of curability (film thickness retention). From these results, it was confirmed that the compound of the present invention can provide a cured product that is excellent in lithography performance and has a high refractive index.

Claims

1. A compound represented by formula (I). 【Chemistry 1】 [In formula (I), L represents a single bond or a divalent group, and a plurality of L's may be the same or different. A represents an oxygen atom or a sulfur atom, and a plurality of A's may be the same or different. n represents an integer of 0 to 6. R represents a monovalent substituent, and when there are a plurality of R, the plurality of R may be the same or different. R ２ represents a hydrogen atom or a monovalent substituent, ２ may be the same or different.

2. A composition comprising the compound of claim 1.

3. The composition of claim 2 further comprising a polymerization initiator.

4. The composition of claim 3 , wherein the polymerization initiator is a thermal cationic polymerization initiator or a thermal anionic polymerization initiator.

5. A cured product of the compound according to claim 1 or the composition according to any one of claims 2 to 4.

6. A display device comprising the cured product according to claim 5 .

7. A solid-state imaging device comprising the cured product according to claim 5 .

8. An encapsulating material comprising a compound according to claim 1 or a composition according to any one of claims 2 to 4.

9. An insulating material comprising a compound according to claim 1 or a composition according to any one of claims 2 to 4.

10. A method for producing a compound represented by formula (IA), comprising the steps of: 【Chemistry 2】 [In formula (IA), L represents a single bond or a divalent group, and a plurality of L's may be the same or different. n represents an integer of 0 to 6. R represents a monovalent substituent, and when there are a plurality of R's, the plurality of R's may be the same or different. R ２ represents a hydrogen atom or a monovalent substituent, ２ may be the same or different. Formula (II): 【Chemistry 3】 [In formula (II), n and R have the same meanings as defined above.] and a compound represented by formula (III): 【Chemistry 4】 [In formula (III), R ２ has the same meaning as above, and X represents a leaving group. and a compound represented by formula (IA) by reacting the compound represented by formula (IA).

11. A method for producing a compound represented by formula (IB), comprising the steps of: 【Chemistry 5】 [In formula (IB), L represents a single bond or a divalent group, and a plurality of L's may be the same or different. A ２ represents an oxygen atom or a sulfur atom, and ２ may be the same or different. ２ At least one of the groups is a sulfur atom. n represents an integer of 0 to 6. R represents a monovalent substituent, and when there are a plurality of R's, the plurality of R's may be the same or different. R ２ represents a hydrogen atom or a monovalent substituent, ２ may be the same or different. Formula (IA): 【Chemistry 6】 [In formula (IA), L, n, R, and R ２ has the same meaning as above.] with a sulfurizing agent to obtain a compound represented by formula (IB).

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