WO2024252940A1 - Compound and composition containing same - Google Patents

Abstract

The present invention addresses the problem of providing a novel compound which can provide a cured article having a high refractive index and which is excellent in film forming properties and curability.　The present invention relates to a compound represented by formula (I). In the formula, R¹ represents a hydrogen atom or a monovalent substituent. L represents a single bond or a divalent group, and the multiple Ls may be the same or different. A represents an oxygen atom or a sulfur atom, and the multiple As may be the same or different. n represents an integer of any of 0-4. R represents a monovalent substituent, and when there are multiple Rs, the multiple Rs may be the same or different.

Description

Compounds and compositions containing same

The present invention relates to a compound. The present invention also relates to a composition containing the compound, a cured product of the compound or the composition, a display device containing the cured product, and a solid-state imaging device containing the cured product.

Highly refractive materials are in demand in the field of optical equipment. Highly refractive materials can be used to obtain lenses, which can control the light path within optical equipment. Lenses are used in solid-state imaging devices to improve the light collection efficiency for each photoelectric conversion element, and in display devices to improve the light extraction efficiency from pixels. Various highly refractive materials have been developed to date (for example, Patent Document 1).

International Publication No. 2011/102258

One object of the present invention is to provide a new compound that can give a cured product that exhibits a high refractive index and has excellent film-forming and curing properties. 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, and a solid-state imaging device containing the cured product.

［式（Ｉ）中、
　Ｒ^１は水素原子又は１価の置換基を表す。
　Ｌは単結合又は２価の基を表し、複数あるＬは同一であっても異なっていてもよい。
　Ａは酸素原子又は硫黄原子を表し、複数あるＡは同一であっても異なっていてもよい。
　ｎは０～４のいずれかの整数を表す。
　Ｒは１価の置換基を表し、Ｒが複数ある場合、複数のＲは同一であっても異なっていてもよい。］
　〔２〕　式（Ｉ）中の下記式で表される基

は、Ｌの結合位置に対してパラ位に結合する〔１〕に記載の化合物。
　〔３〕　Ａが酸素原子である〔１〕又は〔２〕に記載の化合物。
　〔４〕　〔１〕～〔３〕のいずれかに記載の化合物を含む組成物。
　〔５〕　重合開始剤をさらに含む〔４〕に記載の組成物。
　〔６〕　溶剤をさらに含む〔４〕又は〔５〕に記載の組成物。
　〔７〕　〔１〕～〔３〕のいずれかに記載の化合物又は〔４〕～〔６〕のいずれかに記載の組成物の硬化物。
　〔８〕　〔７〕に記載の硬化物を含む表示装置。
　〔９〕　〔７〕に記載の硬化物を含む固体撮像素子。 The present invention includes the following.
[1] A compound represented by formula (I):

[In formula (I),
R ¹ represents a hydrogen atom or a monovalent substituent.
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 4.
R represents a monovalent substituent, and when there are multiple R, the multiple R may be the same or different.
[2] A group represented by the following formula in formula (I):

The compound according to [1], wherein is bonded at the para position relative to the bonding position of L.
[3] The compound according to [1] or [2], wherein A is an oxygen atom.
[4] A composition comprising the compound according to any one of [1] to [3].
[5] The composition according to [4], further comprising a polymerization initiator.
[6] The composition according to [4] or [5], further comprising a solvent.
[7] A cured product of the compound according to any one of [1] to [3] or the composition according to any one of [4] to [6].
[8] A display device comprising the cured product according to [7].
[9] A solid-state imaging device comprising the cured product according to [7].

The present invention can provide a new compound that can give a cured product that exhibits a high refractive index and has excellent film-forming and curing properties. It can also provide a composition containing the compound, a cured product of the compound or the composition, a display device containing the cured product, and a solid-state imaging device containing the cured product.

［式（Ｉ）中、
　Ｒ^１は水素原子又は１価の置換基を表す。
　Ｌは単結合又は２価の基を表し、複数あるＬは同一であっても異なっていてもよい。
　Ａは酸素原子又は硫黄原子を表し、複数あるＡは同一であっても異なっていてもよい。
　ｎは０～４のいずれかの整数を表す。
　Ｒは１価の置換基を表し、Ｒが複数ある場合、複数のＲは同一であっても異なっていてもよい。］ <Compound>
The compound according to the present invention is a compound represented by formula (I) (hereinafter, also referred to as "compound (I)"). Compound (I) can give a cured product exhibiting a high refractive index, and can also exhibit excellent film-forming properties and curing properties. Compound (I) can also exhibit excellent patterning properties.

[In formula (I),
R ¹ represents a hydrogen atom or a monovalent substituent.
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 4.
R represents a monovalent substituent, and when there are multiple R, the multiple R may be the same or different.

が、ベンゼン環の、Ｌが結合している位置を除く任意の位置に結合していてもよいことを表す。また、式（Ｉ）における３つの下記式で表される基

は、各ベンゼン環の同じ位置に結合しなくてもよく、例えば、２つがＬの結合位置に対してパラ位に結合し、残りの１つがメタ位に結合してもよい。
　式（Ｉ）は、ｎが１～３のいずれかの整数を表す場合、各々のＲが、Ｌが結合している位置及び下記式

で表される基が結合している位置を除くベンゼン環の任意の位置に結合していてもよいことを表す。
　３つの下記式

で表される基のうち少なくとも１つの基は、Ｌの結合位置に対してパラ位に結合していることが好ましく、すべての基がＬの結合位置に対してパラ位に結合していることがより好ましい。 Formula (I) is a group represented by the following formula:

may be bonded to any position of the benzene ring except the position to which L is bonded.

may not be bonded to the same position on each benzene ring; for example, two of them may be bonded to the para position with respect to the bonding position of L, and the remaining one may be bonded to the meta position.
In formula (I), when n is an integer of 1 to 3, each R is a position where L is bonded and a group represented by the following formula:

It means that it may be bonded to any position on the benzene ring except for the position to which the group represented by the following formula is bonded.
The three following formulas

At least one of the groups represented by the following formula (I) is preferably bonded at the para position relative to the bonding position of L, and it is more preferable that all of the groups are bonded at the para position relative to the bonding position of L.

In formula (I), R ¹ represents a hydrogen atom or a monovalent substituent. Examples of the monovalent substituent include monovalent hydrocarbon groups and other substituents. Examples of R ¹ representing a monovalent hydrocarbon group 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 a combination of two or more of these (such as aralkyl groups).

One or more -CH ₂ - contained in the monovalent hydrocarbon group may be substituted with -O-, -S-, -NR ^1A - (R ^1A represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms), -CO-, or -SO ₂ -. Examples of the monovalent hydrocarbon group in which -CH ₂ - is substituted with -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.

Substituents that monovalent aliphatic chain hydrocarbon groups, monovalent alicyclic hydrocarbon groups, and monovalent aromatic hydrocarbon groups may have refer to atoms or atomic groups that bond as side chains to the main chain when the molecular chain with the longest chain length among these hydrocarbon groups is taken as the main chain.

Examples of the monovalent aliphatic chain hydrocarbon group include saturated or unsaturated aliphatic chain hydrocarbon groups, and specific examples thereof include alkyl groups such as a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, a hexadecyl group, a heptadecyl group, an octadecyl group, a nonadecyl group, and an eicosyl group.
The monovalent aliphatic chain hydrocarbon group usually has 1 or more and 20 or less carbon atoms, preferably 1 or more and 10 or less, more preferably 1 or more and 6 or less, even more preferably 1 or 2 carbon atoms.

Specific examples of the substituent that the monovalent aliphatic chain hydrocarbon group may have include those described below as specific examples of the substituent that the divalent aliphatic chain hydrocarbon group may have. The monovalent aliphatic chain hydrocarbon group may have one or more substituents.
The same applies to the substituents which the monovalent alicyclic hydrocarbon group may have and the substituents which the monovalent aromatic hydrocarbon group may have.

Examples of the monovalent alicyclic hydrocarbon group include saturated or unsaturated alicyclic hydrocarbon groups, and specific examples thereof include monocyclic alicyclic hydrocarbon groups such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cyclooctyl group, a cyclononyl group, and a cyclodecyl group; and polycyclic alicyclic hydrocarbon groups such as a bicyclo[1.1.0]butyl group, a tricyclo[2.2.1.0]heptyl group, a bicyclo[3.2.1]octyl group, a bicyclo[2.2.2]octyl group, a tricyclo[3.3.1.1 ^3,7 ]decyl group (adamantyl group), a tricyclo[5.2.1.0 ^2,6 ]decyl group, a bicyclo[4.3.2]undecyl group, and a tricyclo[5.3.1.1]dodecyl group.
The monovalent alicyclic hydrocarbon group usually has 3 or more and 20 or less, preferably 3 or more and 10 or less, more preferably 3 or more and 6 or less, and further preferably 5 or 6 carbon atoms.

The monovalent aromatic hydrocarbon group may be monocyclic or polycyclic, and examples thereof 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.

Examples of the other substituents represented by ^R1 include a hydroxy group; an amino group which may be substituted with one or two alkyl groups having 1 to 6 carbon atoms, such as an amino group, a monomethylamino group, a monoethylamino group, a dimethylamino group, a diethylamino group, or a methylethylamino group; a heterocyclic group such as 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, or a furyl group, or 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.

^R1 is preferably a hydrogen atom or a monovalent aliphatic chain hydrocarbon group having 1 to 6 carbon atoms, more preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and even more preferably a hydrogen atom or a methyl group.

In formula (I), each L independently represents a single bond or a divalent group. Examples of the divalent group L include divalent hydrocarbon groups such as an optionally substituted divalent aliphatic chain hydrocarbon group, an optionally substituted divalent alicyclic hydrocarbon group, an optionally substituted divalent aromatic hydrocarbon group, and a divalent group that is a combination of two or more of these (such as an aralkylene group).
One or more -CH _{2 -} contained in the divalent hydrocarbon group may be substituted with -O-, -S-, -NR ^1B - (R ^1B represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms), -CO-, or -SO ₂ -.

The divalent aliphatic chain hydrocarbon group and the divalent alicyclic hydrocarbon group may each be a saturated hydrocarbon group or an unsaturated hydrocarbon group. The divalent aliphatic chain hydrocarbon group and the divalent alicyclic hydrocarbon group are each preferably saturated hydrocarbon groups.

The divalent groups L are each independently preferably a single bond or a divalent hydrocarbon group selected from the group consisting of divalent aliphatic chain hydrocarbon groups which may have a substituent, divalent aromatic hydrocarbon groups which may have a substituent, and divalent groups which are combinations of these.

With respect to each of the three L's in formula (I), the substituent which the divalent aliphatic chain hydrocarbon group, the divalent alicyclic hydrocarbon group and the divalent aromatic hydrocarbon group may have refers to an atom or an atomic group which is bonded as a side chain to the main chain of the molecular chain which bonds between the carbon (C) atom to which ^R1 is bonded and the benzene ring in formula (I).

Examples of the divalent aliphatic chain hydrocarbon group include saturated or unsaturated aliphatic chain hydrocarbon groups. Specific examples of the divalent aliphatic chain hydrocarbon group include alkanediyl groups such as a methylene group, an ethylene group, a propanediyl group, a butanediyl group, a pentanediyl group, a hexanediyl group, a heptanediyl group, an octanediyl group, a nonanediyl group, a decanediyl group, an undecanediyl group, a dodecanediyl group, a tridecanediyl group, a tetradecanediyl group, a pentadecanediyl group, a hexadecanediyl group, a heptadecanediyl group, an octadecanediyl group, a nonadecanediyl group, and an eicosanediyl group.
The divalent aliphatic chain hydrocarbon group has usually 1 or more and 30 or less, preferably 1 or more and 20 or less, more preferably 1 or more and 10 or less, and further preferably 1 or more and 4 or less, and may have 1 or 2 carbon atoms.

Examples of the substituent that the divalent aliphatic chain hydrocarbon group may have include halogen atoms such as fluorine atom, chlorine atom, bromine atom, iodine atom, etc., hydroxy group, amino group, acetyl group, benzoyl group, carboxy group, carboxylate group (e.g., alkyloxycarbonyl group, etc.), cyano group, monovalent aliphatic chain hydrocarbon group, monovalent alicyclic hydrocarbon group, monovalent aromatic hydrocarbon group, etc. The divalent aliphatic chain hydrocarbon group can have one or more substituents.
The same applies to the substituents which the divalent alicyclic hydrocarbon group may have and the substituents which the divalent aromatic hydrocarbon group may have.

The monovalent aliphatic chain hydrocarbon group and the monovalent alicyclic hydrocarbon group which are the substituents may each be linear or branched.
Specific examples of the monovalent aliphatic chain hydrocarbon group, monovalent alicyclic hydrocarbon group, and monovalent aromatic hydrocarbon group which are the substituents include those respectively described above as specific examples of the monovalent aliphatic chain hydrocarbon group, monovalent alicyclic hydrocarbon group, and monovalent aromatic hydrocarbon group which are ^R1 in formula (I).

Examples of the divalent alicyclic hydrocarbon group include saturated or unsaturated alicyclic hydrocarbon groups, and specific examples thereof include monocyclic alicyclic hydrocarbon groups such as a cyclopropanediyl group, a cyclobutanediyl group, a cyclopentanediyl group, a cyclohexanediyl group, a cyclooctanediyl group, a cyclononanediyl group, and a cyclodecanediyl group; a bicyclo[1.1.0]butanediyl group, a tricyclo[2.2.1.0]heptanediyl group, a bicyclo[3.2.1]octanediyl group, a bicyclo[2.2.2]octanediyl group, a tricyclo[3.3.1.1 ^3,7 ]decanediyl group (adamantanediyl group), a tricyclo[5.2.1.0 ^2,6 ]decanediyl group, bicyclo[4.3.2]undecanediyl group, tricyclo[5.3.1.1]dodecanediyl group, and other polycyclic alicyclic hydrocarbon groups.
The divalent alicyclic hydrocarbon group usually has 3 or more and 30 or less, preferably 3 or more and 20 or less, and more preferably 3 or more and 10 or less, and may have 5 or 6 carbon atoms.

The divalent aromatic hydrocarbon group may be monocyclic or polycyclic, and examples thereof include a phenylene group, a naphthylene group, an anthracenediyl group, and a fluorenediyl group.
The divalent aromatic hydrocarbon group usually has 6 or more and 20 or less carbon atoms, and preferably has 6 or more and 10 or less carbon atoms.

An example of a divalent group that is a combination of a divalent aliphatic chain hydrocarbon group that may have a substituent and a divalent aromatic hydrocarbon group that may have a substituent is a divalent group that is a combination of a phenylene group and an alkanediyl group.

Specific examples of L, which is a divalent group, include the following. However, L is not limited to the following. In the following formulas, * indicates a bond to the carbon (C) atom to which ^R1 is bonded or a bond to the benzene ring in formula (I).

L is preferably as follows:

In formula (I), A represents an oxygen atom or a sulfur atom, and is preferably an oxygen atom.
In formula (I), R represents a monovalent substituent. Specific examples of R include those mentioned above as specific examples of the monovalent substituent represented by ^R1 in formula (I).
In formula (I), n represents an integer of 0 to 4, and is preferably 0 or 1.

Examples of compound (I) include the following compounds.

［式（ＩＩ）中、Ｒ^１、Ｌ、Ａ、ｎ及びＲは前記と同じ意味を表す。］
で表される化合物と、式（ＩＩＩ）

［式（ＩＩＩ）中、Ｘは脱離基を表す。］
で表される化合物とを反応させることにより、式（ＩＶ）

［式（ＩＶ）中、Ｒ^１、Ｌ、Ａ、ｎ及びＲは前記と同じ意味を表す。］
で表される化合物を得る工程；
　第２工程：前記式（ＩＶ）で表される化合物と硫化剤との反応により、前記式（Ｉ）で表される化合物を得る工程 <Method of producing the compound>
Compound (I) can be produced by a method including the following first and second steps.
First step: Formula (II)

[In formula (II), R ¹ , L, A, n and R have the same meanings as defined above.]
and a compound represented by formula (III)

[In formula (III), X represents a leaving group.]
With a compound represented by formula (IV)

[In formula (IV), R ¹ , L, A, n and R have the same meanings as defined above.]
obtaining a compound represented by the formula:
Step 2: A step of obtaining a compound represented by formula (I) by reacting a compound represented by formula (IV) with a sulfurizing agent.

The reaction of the compound represented by formula (II) (hereinafter also referred to as "compound (II)") with the compound represented by formula (III) (hereinafter also referred to as "compound (III)") in the first step can be carried out, for example, in the presence of a base. Two or more types of bases may be used in combination. 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, DABCO, pyridine, 2,6-dimethylpyridine, 2,6-di-t-butylpyridine, dimethylaminopyridine, triphenylphosphine, tetramethylammonium bromide, and tetramethylammonium chloride. The amount of base used is, for example, 0.01 to 10 moles, preferably 0.5 to 5 moles, per mole of compound (II).

In formula (III), examples of the leaving group represented by X include halogen atoms such as fluorine, chlorine, bromine, and iodine; alkylsulfonyl groups such as methylsulfonyl, ethylsulfonyl, propylsulfonyl, butylsulfonyl, trifluoromethylsulfonyl, perfluoroethylsulfonyl, perfluoropropylsulfonyl, and perfluorobutylsulfonyl; and arylsulfonyl groups such as phenylsulfonyl, p-toluenesulfonyl, p-fluorophenylsulfonyl, and pentafluorophenylsulfonyl. An example of compound (III) is an epihalohydrin compound (a compound in which X is a halogen atom). The amount of compound (III) used is, for example, 0.01 to 20 moles, and preferably 0.5 to 15 moles, per mole of compound (II). Two or more types of compound (III) may be used to carry out the first step.

The reaction between compound (II) and compound (III) is preferably carried out in a solvent. Examples of the solvent include water and organic solvents such as ketones, aromatic hydrocarbons, halogenated aromatic hydrocarbons, aliphatic hydrocarbons, halogenated aliphatic hydrocarbons, ethers, alcohols, glymes, esters, aliphatic nitriles, sulfoxides, and amides. Two or more types of solvents may be used in combination. Specific examples of organic solvents include the following:

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, 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, and the like. Glymes: methyl diglyme, ethyl diglyme, triglyme, diethylene glycol butyl methyl ether, and the like. Esters: methyl acetate, ethyl acetate, propyl acetate, butyl acetate, and the like. Aliphatic nitriles: acetonitrile, and the like. Sulfoxides: dimethyl sulfoxide, sulfolane, and the like. Amides: N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, and the like.

The temperature for the reaction of compound (II) with compound (III) is, for example, −80 to 200° C., preferably 0 to 150° C. After the reaction, the compound represented by formula (IV) (hereinafter also referred to as “compound (IV)”) obtained may be isolated or may be subjected to the second step without being isolated.

The reaction carried out in the second step is a reaction in which the oxygen atom of the epoxy group in compound (IV) is replaced with a sulfur atom using a sulfurizing agent to form a thiirane group (episulfide group). Examples of the sulfurizing agent include thiourea, methylthiourea, dimethylthiourea, trimethylthiourea, tetramethylthiourea, tetraethylthiourea, ethylenethiourea, sodium thiocyanate, and potassium thiocyanate. The amount of the sulfurizing agent used is, for example, 0.01 to 20 moles, and preferably 0.5 to 10 moles, per mole of compound (IV).

The reaction between compound (IV) and the sulfurizing agent is preferably carried out in a solvent. The organic solvents exemplified above can be used as the solvent. Two or more organic solvents may be used in combination. The temperature for the reaction between compound (IV) and the sulfurizing agent is, for example, -80 to 200°C, and preferably 0 to 100°C.

In the second step, a polymerization inhibitor may be added to inhibit polymerization of the produced compound (I). Examples of the polymerization inhibitor include acids and acid anhydrides. Specifically, inorganic acidic compounds such as nitric acid, hydrochloric acid, perchloric acid, hypochlorous acid, chlorine dioxide, hydrofluoric acid, sulfuric acid, fuming sulfuric acid, 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, nitric acid anhydride, sulfuric acid anhydride, boron oxide, arsenic acid pentoxide, phosphorus pentoxide, chromic acid anhydride, silica gel, silica alumina, aluminum chloride, and zinc chloride; 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, cyclohexane carboxylic acid, thiodipropionic acid, dithiodipropionic acid acetic acid, maleic acid, benzoic acid, phenyl organic carboxylic acids such as ethyl acetic 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 portion of these is a phosphite. , organic phosphorus compounds such as dialkyl dithiophosphates represented by dimethyl dithiophosphate, phenol, catechol, t-butylcatechol, 2,6-di-t-butylcresol, 2,6-di-t-butylethylphenol, resorcin, hydroquinone, phloroglucin, pyrogallol, cresol, ethylphenol, butylphenol, nonylphenol, hydroxyphenylacetic acid, hydroxyphenylpropionic acid, hydroxyphenylacetic acid amide, hydroxyphenyl methyl acetate, hydroxyphenyl ethyl acetate, 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, 2,4,6-trichlorophenol and other phenols, 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's acid, phenyl J acid and other sulfonic acids, and the like, and it is also possible to use a plurality of them in combination. The amount of the polymerization inhibitor used is, for example, 0.0001 to 1.0 mole, preferably 0.01 to 0.2 mole, relative to 1 mole of compound (IV). Preferred polymerization inhibitors are acetic acid, acetic anhydride, maleic acid, and maleic anhydride.

In the second step, the product solution after the reaction is washed with an acidic aqueous solution to improve the stability over time of the obtained compound (I). 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, maleic acid, etc. These may be used alone or in combination of two or more. Aqueous solutions of these acids are usually effective at pH 6 or less, but are more effective at pH 3 or less. Hydrochloric acid and sulfuric acid are preferred.

Furthermore, in order to improve the stability of compound (I) in the second step, a hydrogen sulfide adsorbent can be used. Examples of hydrogen sulfide adsorbents include iron (III) hydroxide, zinc oxide, KNK-301 (zinc oxide-based adsorbent, manufactured by Kureha Oil & Fat Industries Co., Ltd.), Nionon 202A (iron oxide-based adsorbent, manufactured by Ibuki Seisakusho Co., Ltd.), and Limonic (iron hydroxide-based, manufactured by Nippon Limonic Co., Ltd.). The hydrogen sulfide adsorbent can be added during the reaction in the second step, or can be used in the purification after the reaction.

<Composition>
The composition according to the present invention (hereinafter, also referred to as "composition (I)") may contain compound (I) and other components other than compound (I). Composition (I) may contain two or more types of compound (I). Since compound (I) has curability, composition (I) can be cured by irradiation with active energy rays or heating. By curing composition (I), a molded product containing a cured product of composition (I) can be formed. The molded product containing the cured product refers to an article containing the cured product and molded into a desired shape.

Since composition (I) contains compound (I), it can exhibit high refractive index and excellent curing properties. In addition, composition (I) can exhibit excellent film-forming properties. Furthermore, composition (I) can exhibit excellent patterning properties.

The content of compound (I) in composition (I) is preferably 1% by mass or more, more preferably 2% by mass or more, and even more preferably 5% by mass or more, based on the total amount of solids in composition (I), and may be 100% by mass or less, preferably 99% by mass or less, more preferably 95% by mass or less, and may be 90% by mass or less, 80% by mass or less, 70% by mass or less, or 60% by mass or less.

The total amount of solids in composition (I) means the sum of the components contained in composition (I) 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 or gas chromatography. The content of each component in the solids of composition (I) may be calculated from the blending ratio at the time of preparing the composition.

The other components contained in composition (I) include, for example, a resin, a curable compound other than compound (I), a polymerization initiator, a solvent, and additives. Examples of additives include inorganic particles, fillers, polymerization initiator assistants, photosensitizers, leveling agents, stabilizers, surfactants, antistatic agents, lubricants, antifouling agents, UV absorbers, antioxidants, and dispersants. Composition (I) may contain two or more of the other components. When composition (I) contains an additive, two or more of the additives may be used in combination.

(1) Resin The composition (I) may contain one or more resins. By containing a resin in the composition (I), it is possible to impart or improve developability to the cured product of the composition (I), or 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.

Examples of thermoplastic resins include olefin-based resins such as polyethylene resin, polypropylene resin, and polycycloolefin resin, (meth)acrylic resins such as poly(meth)acrylic acid ester resin, polystyrene-based resin, styrene-acrylonitrile-based resin, acrylonitrile-butadiene-styrene-based resin, polyvinyl chloride-based resin, polyvinylidene chloride-based resin, polyvinyl acetate-based resin, polyvinyl butyral-based resin, ethylene-vinyl acetate copolymer, ethylene-vinyl alcohol-based resin, polyethylene terephthalate resin, polybutylene terephthalate resin, polyester-based resins such as liquid crystal polyester resin, polyacetal resin, polyamide resin, polycarbonate resin, polyurethane resin, and polyphenylene sulfide resin. One or more of these resins may be used as a polymer blend or polymer alloy.

Curable resins include resins having a photopolymerizable group or a thermally polymerizable group, such as (meth)acrylic resins, epoxy resins, melamine resins, unsaturated polyester resins, phenolic resins, urea resins, alkyd resins, and polyimide resins. In this specification, (meth)acrylic acid means acrylic acid and/or methacrylic acid. The same applies to "(meth)acryloyl" and "(meth)acrylate", etc.

The resin may be an alkali-soluble resin. When composition (I) contains an alkali-soluble resin, it is possible to impart or improve developability to the cured product of composition (I). An alkali-soluble resin is a resin that is soluble in an aqueous alkaline solution. Specific examples include resins having a carboxy group and/or a phenolic hydroxyl group.

The acid value of the alkali-soluble resin is preferably 10 to 170 mgKOH/g, more preferably 20 to 150 mgKOH/g, and even more preferably 30 to 140 mgKOH/g, from the viewpoint of improving the developability and solvent resistance of the cured product of composition (I). 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.

Another example of a resin is a high refractive index resin. A high refractive index resin is a resin with a refractive index of 1.60 or more at a wavelength of 550 nm.

The resin has a weight average molecular weight (Mw) in terms of standard polystyrene, measured by gel permeation chromatography (GPC), of, for example, 1000 to 9000, preferably 2000 to 8500, and more preferably 3000 to 8500. In order to set the Mw of the resin within the above range, it is possible to adjust the reaction conditions, such as the selection of raw materials used, the charging method, and the reaction temperature and time, in an appropriate combination.

When composition (I) contains a resin, the content of the resin in composition (I) 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 composition (I).

(2) Curable Compound Other Than Compound (I) The composition (I) may contain one or more curable compounds other than the compound (I). By containing a curable compound other than the compound (I) in the composition (I), it is possible to adjust the refractive index, viscosity or curability of the composition (I), or to adjust the mechanical properties and/or optical properties of the obtained cured product and a molded product containing the same.

Examples of curable compounds other than compound (I) include episulfide compounds other than compound (I), epoxy compounds, oxetane compounds, hydroxy compounds, vinyl ether compounds, allyl compounds, thiol compounds, polyphenol compounds, iso(thio)cyanate compounds, (meth)acrylate compounds, etc.

When composition (I) contains a curable compound other than compound (I), the content of the curable compound in composition (I) is preferably 1 mass% or more, more preferably 2 mass% or more, and preferably 70 mass% or less, more preferably 60 mass% or less, even more preferably 50 mass% or less, and even more preferably 40 mass% or less, based on the total amount of solids in composition (I).

［式（Ｖ）中、
　Ｌ^ｘは２価の基を表し、複数あるＬ^ｘは同一であっても異なっていてもよい。
　ｐは０又は１を表し、複数あるｐは同一であっても異なっていてもよい。
　ｑは０～６のいずれかの整数を表す。
　Ｒ^ｘは１価の置換基を表し、Ｒ^ｘが複数ある場合、複数のＲ^ｘは同一であっても異なっていてもよい。
　Ｒ^２ｘは水素原子又は１価の置換基を表し、複数あるＲ^２ｘは同一であっても異なっていてもよい。］ An example of an episulfide compound other than compound (I) is a compound represented by formula (V) (hereinafter, also referred to as "compound (V)"). Compound (V) can give a cured product exhibiting a high refractive index and can also exhibit excellent film-forming properties and curing properties, and is therefore suitable for use in combination with compound (I).

[In formula (V),
^Lx represents a divalent group, and a plurality of Lx ^'s may be the same or different.
p represents 0 or 1, and multiple p's may be the same or different.
q represents an integer of 0 to 6.
R ^x represents a monovalent substituent, and when there are a plurality of R ^{x s} , the plurality of R ^{x s} may be the same or different.
R ^2x represents a hydrogen atom or a monovalent substituent, and a plurality of R ^2x may be the same or different.

がいずれもナフタレン環の１～４位の任意の位置に結合しているか、若しくはいずれも５～８位の任意の位置に結合していてもよいこと、又は、一方の基がナフタレン環の１～４位の任意の位置に結合し、かつ他方の基がナフタレン環の５～８位の任意の位置に結合していてもよいことを表す。また、式（Ｖ）は、Ｒ^ｘで表される１以上の１価の置換基を有する場合、該１以上の１価の置換基が、上記式で表される基が結合している位置を除くナフタレン環の１～８位の任意の位置に結合していてもよいことを表す。後述する式（Ｖａ）、式（Ｖｂ）、式（Ｖｃ）、式（Ｖｄ）、式（Ｖｅ）、式（ＶＩ）及び式（ＶＩＩ）についても同様である。 Formula (V) is a compound represented by two groups of the following formula:

represents that either one of the groups may be bonded to any one of the 1st to 4th positions of the naphthalene ring, or either one of the groups may be bonded to any one of the 5th to 8th positions of the naphthalene ring, or one of the groups may be bonded to any one of the 1st to 4th positions of the naphthalene ring, and the other group may be bonded to any one of the 5th to 8th positions of the naphthalene ring. In addition, when formula (V) has one or more monovalent substituents represented by R ^x , the one or more monovalent substituents may be bonded to any one of the 1st to 8th positions of the naphthalene ring, except for the position to which the group represented by the above formula is bonded. The same applies to formulas (Va), (Vb), (Vc), (Vd), (Ve), (VI), and (VII) described later.

In formula (V), the two ^Lx's representing a divalent group each independently include a divalent hydrocarbon group such as 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, and a divalent group formed from a combination thereof (e.g., an aralkylene group).
The —CH ₂ — contained in the divalent hydrocarbon group may be substituted by —O—, —S—, —NR ^1C — (R ^1C represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms), —CO— or —SO ₂ —.

The divalent aliphatic chain hydrocarbon group may be, for example, a saturated or unsaturated aliphatic chain hydrocarbon group, and specifically may be an alkanediyl group such as a methylene group, an ethylene group, a propanediyl group, a butanediyl group, a pentanediyl group, a hexanediyl group, a heptanediyl group, an octanediyl group, a nonanediyl group, a decanediyl group, an undecanediyl group, a dodecanediyl group, a tridecanediyl group, a tetradecanediyl group, a pentadecanediyl group, a hexadecanediyl group, a heptadecanediyl group, an octadecanediyl group, a nonadecanediyl group, or an 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 even more preferably 1 or 2.

Examples of the substituents that the divalent aliphatic chain hydrocarbon group may have include halogen atoms such as fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms, hydroxyl groups, amino groups, acetyl groups, and cyano groups.

Examples of divalent alicyclic hydrocarbon groups include saturated or unsaturated alicyclic hydrocarbon groups, and specific examples thereof 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.

Examples of the substituents that the divalent alicyclic 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; hydroxyl, amino, acetyl, and cyano groups.

The divalent aromatic hydrocarbon group may be monocyclic or polycyclic, and examples thereof 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.

Examples of the substituents 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; hydroxyl, amino, acetyl, and cyano groups.

Preferably, at least one of the two ^Lx in formula (V) is an alkanediyl group, more preferably both are alkanediyl groups. In this case, the alkanediyl group preferably has 1 to 10 carbon atoms, more preferably 1 to 6 carbon atoms, even more preferably 1 to 4 carbon atoms, and even more preferably 1 or 2 carbon atoms.

In formula (V), two p's are each independently 0 or 1, and preferably 0. More preferably, two p's are both 0.
q is an integer of 0 to 6, preferably an integer of 0 to 4, more preferably an integer of 0 to 2, even more preferably 0 or 1, and particularly preferably 0.

In formula (V), R ^x representing a monovalent substituent, when there are a plurality of R ^x , each independently represents, for example, a monovalent hydrocarbon group such as a monovalent aliphatic chain hydrocarbon group which may have a substituent, a monovalent alicyclic hydrocarbon group which may have a substituent, a monovalent aromatic hydrocarbon group which may have a substituent, or a monovalent group consisting of a combination thereof (such as an aralkyl group); a hydroxy group; an alkyl group having one or two carbon atoms, such as an amino group, a monomethylamino group, a monoethylamino group, a dimethylamino group, a diethylamino group, or a methylethylamino group; Examples of the heterocyclic group include an amino group which may be substituted with a group; 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, or 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 _-CH2- contained in the monovalent hydrocarbon group may be substituted with -O-, -S-, ^-NR1D- ( ^R1D represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms), -CO-, or _-SO2- . Examples of monovalent hydrocarbon groups in which -CH ₂ - is replaced with -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.

Examples of the monovalent aliphatic chain hydrocarbon group include saturated or unsaturated aliphatic chain hydrocarbon groups, and specific 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 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 even more preferably 1 or 2.

Examples of the substituents that the monovalent aliphatic chain hydrocarbon group may have include halogen atoms such as fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms, hydroxyl groups, amino groups, acetyl groups, and cyano groups.

Examples of monovalent alicyclic hydrocarbon groups include saturated or unsaturated alicyclic hydrocarbon groups, specifically, 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 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.

Examples of the substituents 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 methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, and decyl; halogen atoms, such as fluorine, chlorine, bromine, and iodine; hydroxyl, amino, acetyl, and cyano groups.

The monovalent aromatic hydrocarbon group may be monocyclic or polycyclic, and examples thereof 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.

Examples of the substituents 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 methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, and decyl; halogen atoms, such as fluorine, chlorine, bromine, and iodine; hydroxyl, amino, acetyl, and cyano groups.

In formula (V), R ^2x represents a hydrogen atom or a monovalent substituent, and multiple R ^2x may be the same or different, and are preferably the same. Specific examples of the monovalent substituent include those same as R ^x . Each of the two R ^2x is 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, 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.

Compounds represented by formula (V) include compounds represented by formula (Va), formula (Vb), formula (Vc), formula (Vd) and formula (Ve). In formula (Va), formula (Vb), formula (Vc), formula (Vd) and formula (Ve), q, ^Rx , ^R2x , ^Lx and p have the same meanings as in formula (V).

In formula (Va), formula (Vb), formula (Vc), formula (Vd) and formula (Ve), preferably, at least one of the two Lx ^'s 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, and even more preferably 1 or 2.

In formula (Va), formula (Vb), formula (Vc), formula (Vd), and formula (Ve), two p's are each independently 0 or 1, and preferably 0. More preferably, two p's are both 0.
q is an integer of 0 to 6, preferably an integer of 0 to 4, more preferably an integer of 0 to 2, even more preferably 0 or 1, and particularly preferably 0.

In formulae (Va), (Vb), (Vc), (Vd) and (Ve), two R ^2x 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, 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. Two R ^2x are preferably the same.

From the viewpoint of synthesis, the molecular weight of compound (V) is preferably 2000 or less, more preferably 1000 or less, and even more preferably 500 or less. From the viewpoint of volatility, the molecular weight is preferably 50 or more, more preferably 100 or more, and even more preferably 150 or more.

［式（ＶＩ）中、ｑ及びＲ^ｘは前記と同じ意味を表す。］
で表される化合物と、式（ＶＩＩ）

［式（ＶＩＩ）中、Ｒ^２ｘ、Ｌ^ｘ及びｐは前記と同じ意味を表し、Ｘ^ｘは脱離基を表す。］
で表される化合物とを反応させることにより、式（ＶＩＩＩ）

［式（ＶＩＩＩ）中、ｑ、Ｒ^ｘ、Ｒ^２ｘ、Ｌ^ｘ及びｐは前記と同じ意味を表す。］
で表される化合物を得る工程；
　第２工程：前記式（ＶＩＩＩ）で表される化合物と硫化剤との反応により、化合物（Ｖ）を得る工程 <Method of producing the compound>
Compound (V) can be produced by a method including the following first and second steps.
First step: Formula (VI)

[In formula (VI), q and ^Rx have the same meanings as defined above.]
and a compound represented by formula (VII)

[In formula (VII), R ^2x , L ^x and p are as defined above, and X ^x represents a leaving group.]
With a compound represented by formula (VIII)

[In formula (VIII), q, R ^x , R ^2x , L ^x and p have the same meanings as defined above.]
obtaining a compound represented by the formula:
Step 2: A step of obtaining compound (V) by reacting the compound represented by formula (VIII) with a sulfurizing agent.

The reaction of the compound represented by formula (VI) (hereinafter also referred to as "compound (VI)") with the compound represented by formula (VII) (hereinafter also referred to as "compound (VII)") in the first step can be carried out, for example, in the presence of a base. Two or more types of bases may be used in combination. 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, DABCO, pyridine, 2,6-dimethylpyridine, 2,6-di-t-butylpyridine, dimethylaminopyridine, triphenylphosphine, tetramethylammonium bromide, and tetramethylammonium chloride. The amount of base used is, for example, 0.01 to 10 moles, preferably 0.5 to 5 moles, per mole of compound (VI).

In formula (VII), examples of the leaving group represented by X ^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. An example of compound (VII) is an epihalohydrin compound (a compound in which X ^x is a halogen atom, L ^x is a methylene group, and p is 0). The amount of compound (VII) used is, for example, 0.01 to 20 moles, preferably 0.5 to 15 moles, relative to 1 mole of compound (VI). Two or more kinds of compound (VII) may be used to carry out the first step.

The reaction between compound (VI) and compound (VII) is preferably carried out in a solvent. Examples of the solvent include water and organic solvents such as ketones, aromatic hydrocarbons, halogenated aromatic hydrocarbons, aliphatic hydrocarbons, halogenated aliphatic hydrocarbons, ethers, alcohols, glymes, esters, aliphatic nitriles, sulfoxides, and amides. Two or more types of solvents may be used in combination.

The temperature for the reaction between compound (VI) and compound (VII) is, for example, −80 to 200° C., preferably 0 to 150° C. After the reaction, the compound represented by formula (VIII) (hereinafter also referred to as "compound (VIII)") obtained may be isolated or may be subjected to the second step without being isolated.

The reaction carried out in the second step is a reaction in which the oxygen atom of the epoxy group or oxetanyl group in compound (VIII) is replaced with a sulfur atom using a sulfurizing agent to form a thiirane group (episulfide group) or a thietane group. Examples of the sulfurizing agent include thiourea, methylthiourea, dimethylthiourea, trimethylthiourea, tetramethylthiourea, tetraethylthiourea, ethylenethiourea, sodium thiocyanate, and potassium thiocyanate. The amount of the sulfurizing agent used is, for example, 0.01 to 20 moles, and preferably 0.5 to 10 moles, per mole of compound (VIII).

The reaction between compound (VIII) and the sulfurizing agent is preferably carried out in a solvent. The organic solvents exemplified above can be used as the solvent. Two or more organic solvents may be used in combination. The temperature for the reaction between compound (VIII) and the sulfurizing agent is, for example, −80 to 200° C., and preferably 0 to 100° C.

In the second step, a polymerization inhibitor may be added to inhibit the polymerization of the produced compound (V). Examples of the polymerization inhibitor include acids and acid anhydrides, and preferred are acetic acid, acetic anhydride, maleic acid, and maleic anhydride. The amount of the polymerization inhibitor used is, for example, 0.0001 to 1.0 mol, and preferably 0.01 to 0.001 mol, per mol of compound (VIII).
It is 2 moles.

(3) Polymerization initiator The composition (I) 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 the polymerization of the compound (V) when the composition (I) further contains the compound (V)). For example, a radical polymerization initiator, a cationic polymerization initiator, an anionic polymerization initiator, a radical and a cationic polymerization initiator, etc., may be mentioned, and may be appropriately selected and used. The radical polymerization initiator, the cationic polymerization initiator, and the anionic polymerization initiator generate a radical, an acid, or a base by at least one of active energy ray irradiation and heat, respectively, and cause the radical polymerization, cationic polymerization, or anionic polymerization of the compound (I) and the compound (V). In addition, the compound (I) and the compound (V) may be polymerized and cured by at least one of active energy ray irradiation and heat even in the absence of a polymerization initiator, but it is preferable to contain a polymerization initiator in terms of reactivity.

Examples of thermal 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, aryl ketone compounds, biimidazole compounds, triazine compounds, and acylphosphine compounds.

A cationic polymerization initiator is a compound that can release a substance that initiates cationic polymerization by at least one of active energy ray irradiation and heat. Examples of cationic polymerization initiators include aromatic iodonium salts, aromatic sulfonium salts, aromatic ammonium salts, and cyclopentadienyl iron (II) complexes. These can initiate cationic polymerization by either active energy ray irradiation or heat or both, depending on the difference in their structure. A compound that can release a substance that initiates cationic polymerization by active energy ray irradiation is called a photocationic polymerization initiator, and a compound that can release a substance that initiates cationic polymerization by heat is called a thermal cationic polymerization initiator.

An anionic polymerization initiator is a compound that can release a substance that initiates anionic polymerization by at least one of active energy ray irradiation and heat. Examples of anionic polymerization initiators include borate salts, ammonium salts, DBU (diazabicycloundecenium) salts, DBN (diazabicyclononenium) salts, biguanidium salts, aromatic phosphonium salts, aromatic dimethylurea, and aliphatic dimethylurea. These can initiate anionic polymerization by either active energy ray irradiation or heat, or both, depending on the difference in structure. A compound that can release a substance that initiates anionic polymerization by active energy ray irradiation is called a photoanionic polymerization initiator, and a compound that can release a substance that initiates anionic polymerization by heat is called a thermal anionic polymerization initiator.

When composition (I) contains a polymerization initiator, from the viewpoint of improving the curability and patterning properties of composition (I), composition (I) preferably contains an anionic polymerization initiator.

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

(4) Solvent The composition (I) may contain one or more solvents. The solvent is preferably
The solvent is capable of dissolving or dispersing the compound (I), and more preferably, capable of dissolving or dispersing components other than the compound (I). As the solvent, an organic solvent can be used. Examples of the organic solvent include the following.

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, 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, and the like. Glymes: methyl diglyme, ethyl diglyme, triglyme, diethylene glycol butyl methyl ether, and the like. Esters: methyl acetate, ethyl acetate, propyl acetate, butyl acetate, and the like. Aliphatic nitriles: acetonitrile, and the like. Sulfoxides: dimethyl sulfoxide, sulfolane, and the like. Amides: N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, and the like.

The solvent content in composition (I) is the ratio of the total mass of all solvents contained in composition (I) to the total amount of composition (I). When composition (I) contains a solvent, the solvent content in composition (I) 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, per 100 parts by mass of the solid content of composition (I). When composition (I) contains a solvent, the solid content concentration of composition (I) is preferably 5 to 60 mass%, more preferably 10 to 50 mass%.

<Cured product and molded product>
The present invention provides a cured product of compound (I) or composition (I), and a molded product containing the cured product. Compound (I) and composition (I) have excellent film-forming and curing properties, and are therefore suitable as a curable material for producing a cured product or a molded product containing the same. The cured product can be obtained by curing compound (I) or composition (I) by at least one of active energy ray irradiation and heat. The shape of the molded product containing the cured product is not particularly limited, and may be any shape depending on the application of the molded product, including film (membrane), plate, lens, powder, granule, non-spherical particle, crushed particle, porous, continuous block, fiber, tube, hollow fiber, etc.

The cured product of composition (I) and molded products containing the cured product can exhibit high refractive index because composition (I) contains compound (I). In addition, the cured product of composition (I) and molded products containing the cured product can exhibit excellent patterning properties.

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

In the cast polymerization method, for example, compound (I) or composition (I) is injected into a mold, degassed as necessary, and then cured by heating in an oven or the like, and the resulting molded product is removed. The molded product thus removed can also be irradiated with active energy rays for additional curing.

When forming a film as a molded product on a substrate, compound (I) or composition (I) is applied to the substrate, dried as necessary to form a coating layer, and the coating layer is cured to obtain a molded product that is a cured film. The molded product may be a patterned cured film. A patterned cured film can be obtained by patterning using a method such as photolithography, inkjet printing, or the like. The patterning method is preferably a photolithography method. The photolithography method is a method in which compound (I) or composition (I) is applied to a substrate, dried as necessary to form a coating layer, exposed to light through a photomask, and then developed.

As the substrate, glass plates such as quartz glass, borosilicate glass, alumina silicate glass, and soda lime glass with a silica-coated surface, resin plates such as polycarbonate, polymethylmethacrylate, and polyethylene terephthalate, silicon, and the above substrates on which thin films of aluminum, silver, and silver/copper/palladium alloys are formed can be used. Methods for applying compound (I) or composition (I) to the substrate include spin coating, slit coating, and slit and spin coating.

The light source used for exposure is preferably a light source that generates light with a wavelength of 250 nm or more and 450 nm or less. For example, from the light of this wavelength, light of around 436 nm, around 408 nm, or around 365 nm may be selectively extracted using a bandpass filter depending on the absorption wavelength of the photopolymerization initiator. Specific examples of light sources include mercury lamps, light-emitting diodes, metal halide lamps, and halogen lamps. Heating (pre-development baking) may be performed after pattern exposure and before development.

The developing solution used for development may be, for example, an aqueous solution of an alkaline compound such as potassium hydroxide, sodium bicarbonate, sodium carbonate, or tetramethylammonium hydroxide, or an organic solvent. The organic solvent may be, for example, ketones, aromatic hydrocarbons, halogenated aromatic hydrocarbons, aliphatic hydrocarbons, halogenated aliphatic hydrocarbons, ethers, alcohols, glymes, esters, aliphatic nitriles, sulfoxides, or amides. Two or more types of solvents may be used in combination. The developing solution may contain a surfactant. The developing method may be any of the puddle method, dipping method, and spray method. The patterned film obtained by development may be further heated (post-baked).

The cured product or a molded product containing the same can exhibit a high refractive index because it is formed from compound (I) or composition (I) containing the same, and the refractive index can be controlled to a desired refractive index by adjusting the composition of composition (I). The refractive index of the cured product or a molded product containing the same at a wavelength of 550 nm can be 1.62 or more, 1.63 or more, 1.64 or more, 1.65 or more, 1.68 or more, or 1.70 or more. The refractive index at a wavelength of 550 nm can be, for example, 1.80 or less, or 1.78 or less, 1.75 or less, or 1.73 or less.

[Application]
According to the present invention, it is possible to obtain a cured product or molded product having a high refractive index, or a cured product or molded product having a desired refractive index. The uses of the cured product or molded product include, for example, glass substitutes and surface coating materials thereof; coating materials for window glass, daylighting glass, and light source protection glass for residences, facilities, transport equipment, etc.; window films for residences, facilities, transport equipment, etc.; interior and exterior materials for residences, facilities, transport equipment, etc., and interior and exterior paints and coating films formed by the paints; alkyd resin lacquer paints and coating films formed by the paints; acrylic lacquer paints and coating films formed by the paints; light source members that emit ultraviolet rays such as fluorescent lamps and mercury lamps; precision machinery, electronic and electrical equipment members, and electromagnetic wave blocking materials generated from various displays; containers or packaging materials for food, chemicals, medicines, etc.; bottles, boxes, blisters, cups, special packaging, compact disc coats, agricultural and industrial sheets or films; anti-fading agents for printed matter, dyed matter, dye pigments, etc.; protective films for polymer supports (for example, for plastic parts such as machinery 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 styling products, etc.; textile products and fibers for clothing such as sportswear, stockings, hats, etc.; household interior products 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, indicators, etc. and their surface coating materials; substrates used in optical devices, etc.; optical waveguides; holograms; LED encapsulants; and the like.

The molded article is suitable for use as a lens, which is an optical component used in optical devices. Examples of optical devices include solid-state imaging devices and display devices. Lenses are used in solid-state imaging devices to improve the efficiency of focusing light onto each photoelectric conversion element, and lenses are used in display devices to improve the efficiency of extracting light from pixels. The lens may be a microlens. As display devices, the molded article is suitable for use in liquid crystal display devices, organic EL display devices, etc.

Inorganic compounds such as zirconium oxide and titanium oxide are conventionally known as high refractive index materials. However, when producing molded products containing high refractive index materials made of inorganic compounds, molding can be difficult, for example because etching does not proceed easily, and the high refractive index material can scatter during molding, causing contamination problems. The above problems can be solved by using the high refractive index material of the present invention, which is an organic compound.

The present invention will be explained in more detail below with reference to examples and comparative examples, but the present invention is not limited to these examples. In the examples, percentages and parts indicating the content or amount used are based on mass unless otherwise specified.

　ジムロート冷却管及び温度計を設置した４つ口フラスコ内を窒素雰囲気とし、式（ＶＩ
－１）で表される化合物（１，６－ナフタレンジチオール）　３０部、アセトン　１６５部、純水　４５部、及び式（ＶＩＩ－１）で表される化合物（エピクロロヒドリン）　１３９部を上記フラスコに加えて氷浴中で１５分撹拌した。続いて、別のフラスコに水酸化ナトリウム　１５部、アセトン　６６部、及び純水　２０３部を加えて完溶させたのちに、上記４つ口フラスコに１時間かけて滴下した。滴下したのちに３０℃まで昇温し、３０℃で２時間撹拌した。得られた混合物を精製し、式（ＶＩＩＩ－１）で表される化合物　４６部を得た。 [Production Example 1: Synthesis of compound represented by formula (V-1)]
(1) Synthesis of the compound represented by formula (VIII-1)

A four-neck flask equipped with a Dimroth condenser and a thermometer was filled with nitrogen and a solution of the compound represented by the formula (VI) was added.
30 parts of a compound represented by formula (VII-1) (1,6-naphthalenedithiol), 165 parts of acetone, 45 parts of pure water, and 139 parts of a compound represented by formula (VII-1) (epichlorohydrin) were added to the flask and stirred in an ice bath for 15 minutes. Then, 15 parts of sodium hydroxide, 66 parts of acetone, and 203 parts of pure water were added to another flask and completely dissolved, and then the mixture was added dropwise to the four-neck flask over 1 hour. After the dropwise addition, the temperature was raised to 30°C and stirred at 30°C for 2 hours. The resulting mixture was purified to obtain 46 parts of a compound represented by formula (VIII-1).

LC-MS measurement and ¹ H-NMR analysis were carried out, and it was confirmed that the compound represented by formula (VIII-1) was produced.
^1H -NMR (deuterated chloroform) 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

　ジムロート冷却管及び温度計を設置した４つ口フラスコ内を窒素雰囲気とし、式（ＶＩＩＩ－１）で表される化合物　３部、メタノール　３０部、トルエン　３０部、無水酢酸
　０．０５部、及びチオ尿素　３．８部を上記フラスコに加えて室温下で２４時間撹拌した。得られた混合物を精製し、式（Ｖ－１）で表される化合物　２．５部を得た。 (2) Synthesis of compound represented by formula (V-1)

A four-neck flask equipped with a Dimroth condenser and a thermometer was filled with nitrogen, and 3 parts of the compound represented by formula (VIII-1), 30 parts of methanol, 30 parts of toluene, 0.05 parts of acetic anhydride, and 3.8 parts of thiourea were added to the flask and stirred at room temperature for 24 hours. The resulting mixture was purified to obtain 2.5 parts of the compound represented by formula (V-1).

LC-MS measurement and ¹ H-NMR analysis were carried out, and it was confirmed that the compound represented by formula (V-1) was produced.
^1H -NMR (deuterated chloroform) 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

　ジムロート冷却管及び温度計を設置した４つ口フラスコ内を窒素雰囲気とし、１，１，１－トリス（４－ヒドロキシフェニル）エタン　５部、アセトン　２７．５部、純水　７．５部、及びエピクロロヒドリン　１２．１部を上記フラスコに加えて氷浴中で１５分撹拌した。続いて、別のフラスコに水酸化ナトリウム　２．０部、アセトン　１１部、及び純水　４０部を加えて完溶させたのちに、上記４つ口フラスコに１時間かけて滴下した。滴下したのちにオイルバスで６５℃まで昇温し、６５℃で１時間撹拌した。得られた混合物を精製し、式（ＩＶ－１）で表される化合物　６．２部を得た。 [Example 1: Synthesis of compound represented by formula (I-1)]
(1) Synthesis of compound represented by formula (IV-1)

A four-neck flask equipped with a Dimroth condenser and a thermometer was filled with nitrogen, and 5 parts of 1,1,1-tris(4-hydroxyphenyl)ethane, 27.5 parts of acetone, 7.5 parts of pure water, and 12.1 parts of epichlorohydrin were added to the flask and stirred in an ice bath for 15 minutes. Then, 2.0 parts of sodium hydroxide, 11 parts of acetone, and 40 parts of pure water were added to another flask and completely dissolved, and then dropped into the four-neck flask over 1 hour. After dropping, the temperature was raised to 65°C in an oil bath and stirred at 65°C for 1 hour. The resulting mixture was purified to obtain 6.2 parts of a compound represented by formula (IV-1).

LC-MS measurement and ¹ H-NMR analysis were carried out, and it was confirmed that the compound represented by formula (IV-1) was produced.
¹ H-NMR (deuterated chloroform) δ: 6.96-6.99 (6H), 6.78-6.82 (6H), 4.16-4.20 (3H), 3.9 4-3.95 (3H), 3.32-3.34 (3H), 2.88-2.90 (3H), 2.63-2.75 (3H), 2.06 (3H)
LC-MS; [M+NH ₄ ] ⁺ =492.2

　ジムロート冷却管及び温度計を設置した４つ口フラスコ内を窒素雰囲気とし、式（ＩＶ－１）で表される化合物　５部、トルエン　５０部、メタノール　５０部、チオ尿素　６．０部、及び無水マレイン酸　０．１部を上記フラスコに加えて２５℃中で２４時間撹拌した。得られた混合物を精製し、式（Ｉ－１）で表される化合物　３．４部を得た。 (2) Synthesis of the compound represented by formula (I-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 (IV-1), 50 parts of toluene, 50 parts of methanol, 6.0 parts of thiourea, and 0.1 parts of maleic anhydride were added to the flask and stirred for 24 hours at 25° C. The resulting mixture was purified to obtain 3.4 parts of the compound represented by formula (I-1).

LC-MS measurement and ¹ H-NMR analysis were carried out, and it was confirmed that the compound represented by formula (I-1) was produced.
¹ H-NMR (deuterated chloroform) δ: 6.98-7.01 (6H), 6.79-6.84 (6H), 4.20-4.22 (3H), 3.7 5-3.92 (3H), 3.25-3.31 (3H), 2.61-2.63 (3H), 2.33-2.34 (3H), 2.12 (3H)
LC-MS; [M+H] ⁺ =523.2

　ジムロート冷却管及び温度計を設置した４つ口フラスコ内を窒素雰囲気とし、式（Ｙ０）で表される化合物　５部、トルエン　５０部、メタノール　５０部、チオ尿素　４．８部、及び無水マレイン酸　０．１部を上記フラスコに加えて２５℃中で２４時間撹拌した。得られた混合物を精製し、式（Ｉ－２）で表される化合物　４．６部を得た。 [Example 2: Synthesis of compound represented by formula (I-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 (Y0), 50 parts of toluene, 50 parts of methanol, 4.8 parts of thiourea, and 0.1 parts of maleic anhydride were added to the flask and stirred for 24 hours at 25° C. The resulting mixture was purified to obtain 4.6 parts of the compound represented by formula (I-2).

¹ H-NMR analysis confirmed that the compound represented by formula (I-2) was produced.
¹ H-NMR (deuterated chloroform) δ: 7.14-7.19 (4H), 6.92-7.00 (6H), 6.76-6.82 (6H), 4.11-4.21 (3H), 3.84-3.89 (3H), 3.23-3.29 (3H), 2.59-2.61 (3H), 2.30-2.36 (3H), 2.09 (3H), 1.64 (6H)

[Example 3: Preparation of composition]
100 parts by mass of the compound represented by formula (I-2), 1 part by mass of polymerization initiator A, and 310 parts by mass of cyclopentanone as a solvent were placed in a flask and stirred to obtain a liquid composition. When the composition was visually observed, it was found to be transparent and the blended components were uniformly dissolved.

[Examples 4 to 10 and Comparative Examples 1 to 6: Preparation of Compositions]
Liquid compositions were obtained in the same manner as in Example 3, except that the types of components in the compositions and the amounts added thereof were as shown in Table 1. All compositions were transparent when visually inspected, and it was confirmed that the components were uniformly dissolved.

　〔２〕（Ｉ－２）：式（Ｉ－２）で表される化合物

　〔３〕（Ｖ－１）：式（Ｖ－１）で表される化合物

　〔４〕（Ｙ０）：式（Ｙ０）で表される化合物（２－［４－（２，３－エポキシプロポキシ）フェニル］－２－［４－［１，１－ビス［４－（［２，３－エポキシプロポキシ］フェニル）］エチル］フェニル］プロパン、株式会社プリンテック製「ＴＥＣＨＭＯＲＥ
　ＶＧ３１０１Ｌ」）

　〔５〕（Ｙ１）：式（Ｙ１）で表される化合物（１，６－ビス（グリシジルオキシ）ナフタレン、ＤＩＣ株式会社製「ＥＰＩＣＬＯＮ　ＨＰ－４０３２Ｄ」）

　〔６〕（Ｙ２）：式（Ｙ２）で表される化合物（ポリ（１－ビニルナフタレン）、シグマアルドリッチ社製）

　〔７〕（Ｙ３）：式（Ｙ３）で表される化合物（ビスフェノールＡジグリシジルエーテル、ＤＩＣ社製「ＥＰＩＣＬＯＮ　ＥＸＡ－８５０ＣＲＰ」）

　〔８〕（Ｙ４）：式（Ｙ４）で表される化合物（２，２’－ジグリシジルオキシ－１，１’－ビナフタレン、スガイ化学工業株式会社製「ＤＧＯＢＩＮＬ」）

　〔９〕（Ｙ５）：式（Ｙ５）で表される化合物（９－ビニルカルバゾール、ＴＣＩ社製）

　〔１０〕重合開始剤Ａ：ボレート塩タイプの光アニオン重合開始剤（富士フイルム和光純薬株式会社製「ＷＰＢＧ－３００」）
　〔１１〕重合開始剤Ｂ：重合開始剤Ｂ：ＤＢＮ（ジアザビシクロノネニウム）塩タイプの熱アニオン重合開始剤（サンアプロ株式会社製「Ｕ－ＣＡＴ　１１０２」）
　〔１２〕光増感剤Ａ：１，４－ジエトキシ－ナフタレン Details of the abbreviations of the components shown in Table 1 are as follows.
[1] (I-1): Compound represented by formula (I-1)

[2] (I-2): Compound represented by formula (I-2)

[3] (V-1): Compound represented by formula (V-1)

[4] (Y0): A compound represented by the formula (Y0) (2-[4-(2,3-epoxypropoxy)phenyl]-2-[4-[1,1-bis[4-([2,3-epoxypropoxy]phenyl)]ethyl]phenyl]propane), manufactured by Printec Co., Ltd.
VG3101L"

[5] (Y1): Compound represented by formula (Y1) (1,6-bis(glycidyloxy)naphthalene, "EPICLON HP-4032D" manufactured by DIC Corporation)

[6] (Y2): Compound represented by formula (Y2) (poly(1-vinylnaphthalene), manufactured by Sigma-Aldrich)

[7] (Y3): Compound represented by formula (Y3) (bisphenol A diglycidyl ether, "EPICLON EXA-850CRP" manufactured by DIC Corporation)

[8] (Y4): Compound represented by formula (Y4) (2,2'-diglycidyloxy-1,1'-binaphthalene, "DGOBINL" manufactured by Sugai Chemical Industry Co., Ltd.)

[9] (Y5): Compound represented by formula (Y5) (9-vinylcarbazole, manufactured by TCI)

[10] Polymerization initiator A: borate salt type photoanionic polymerization initiator ("WPBG-300" manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.)
[11] Polymerization initiator B: Polymerization initiator B: DBN (diazabicyclononenium) salt type thermal anionic polymerization initiator ("U-CAT 1102" manufactured by San-Apro Co., Ltd.)
[12] Photosensitizer A: 1,4-diethoxy-naphthalene

[Evaluation test]
(1) Refractive index of cured product (1-1) Preparation of cured film for refractive index measurement 1 (Examples 3 to 6, Comparative Examples 1 to 4)
The composition prepared above was dropped in an amount of about 3 cc onto an alkali-free glass plate (Eagle XG, thickness 0.7 mm, manufactured by Corning Incorporated), and spin-coated using a spin coater (MS-B100, manufactured by Mikasa) under conditions of 1000 rpm and 20 seconds to form a coating layer. The alkali-free glass plate on which the coating layer was formed was heated at 80 ° C. for 2 minutes. Next, the alkali-free glass plate on which the coating layer was formed was exposed to an irradiation energy of 1000 mJ / cm ² in an air atmosphere using a high-pressure mercury lamp proximity UV exposure device (UV-3300SC, manufactured by Ushio). Subsequently, the alkali-free glass plate on which the coating layer was formed after exposure was heated at 120 ° C. for 5 minutes to obtain an alkali-free glass plate on which a cured film was formed. The thickness of the cured film on the alkali-free glass plate was measured using a stylus film thickness gauge (DekTak XT, manufactured by Bruker) and was 1.5 μm.

(1-2) Preparation of cured film for refractive index measurement 2 (Examples 7 to 10)
The composition prepared above was dropped in an amount of about 3 cc onto an alkali-free glass plate (Eagle XG, thickness 0.7 mm, manufactured by Corning Incorporated), and spin-coated using a spin coater (MS-B100, manufactured by Mikasa) at 1000 rpm for 20 seconds to form a coating layer. The alkali-free glass plate on which the coating layer was formed was heated at 80° C. for 2 minutes. Next, the alkali-free glass plate on which the coating layer was formed was heated at 120° C. for 5 minutes to obtain an alkali-free glass plate on which a cured film was formed. The thickness of the cured film on the alkali-free glass plate was measured using a stylus film thickness gauge (DekTak XT, manufactured by Bruker) and found to be 1.5 μm.

(1-3) Measurement of refractive index For the alkali-free glass plate on which the cured film was formed, a visible-ultraviolet spectrophotometer (V-650, manufactured by JASCO) with an integrating sphere unit (ISV-922, manufactured by JASCO) was used to measure the transmission spectrum and reflection spectrum at wavelengths of 300 nm to 800 nm. Of 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, the refractive index of the cured film at a wavelength of 550 nm was calculated based on the Fresnel formula (Hecht Optics I Original 5th Edition, Maruzen Publishing, 2018, p. 209-p. 226) from the value of the wavelength of 550 nm and the refractive index of the alkali-free glass plate (Eagle XG, manufactured by Corning). The results are shown in Table 1.

(2) Film-Forming Properties (2-1) Preparation of Coating Layer for Film-Forming Properties Evaluation (Examples 3 to 10, Comparative Examples 1 to 6)
About 3 cc of the composition prepared above was dropped onto an alkali-free glass plate (Eagle XG, thickness 0.7 mm, manufactured by Corning Incorporated) and spin-coated at 1000 rpm for 20 seconds using a spin coater (MS-B100, manufactured by Mikasa) to form a coating layer. The alkali-free glass plate on which the coating layer was formed was heated at 60° C. for 2 minutes.

(2-2) Evaluation of Film Formability The obtained coating layer was observed, and the film formability of the composition was evaluated according to the following evaluation criteria. The results are shown in Table 1. The hole defect refers to a state in which a hole-shaped portion having a diameter of 1 mm or more in which the alkali-free glass plate was exposed was generated in the coating layer.
A: Colorless and transparent, with neither hole defects nor cloudiness. C: Hole defects are present. D: Cloudiness is present.

(3) Curability (3-1) Preparation of cured film for curability evaluation 1 (Examples 3 to 6, Comparative Examples 1 to 4)
The composition prepared above was dropped in an amount of about 3 cc onto an alkali-free glass plate (Eagle XG, thickness 0.7 mm, manufactured by Corning Incorporated), and spin-coated using a spin coater (MS-B100, manufactured by Mikasa) under conditions of 1000 rpm and 20 seconds to form a coating layer. The alkali-free glass plate on which the coating layer was formed was heated at 80 ° C. for 2 minutes. Next, the alkali-free glass plate on which the coating layer was formed was exposed to an irradiation energy of 1000 mJ / cm ² in an air atmosphere using a high-pressure mercury lamp proximity UV exposure device (UV-3300SC, manufactured by Ushio). Subsequently, the alkali-free glass plate on which the coating layer was formed after exposure was heated at 120 ° C. for 5 minutes to obtain an alkali-free glass plate on which a cured film was formed. The thickness of the cured film on the alkali-free glass plate was measured using a stylus film thickness gauge (DekTak XT, manufactured by Bruker) and was 1.5 μm.

(3-2) Preparation of cured film for curability evaluation 2 (Examples 7 to 10)
The composition prepared above was dropped in an amount of about 3 cc onto an alkali-free glass plate (Eagle XG, thickness 0.7 mm, manufactured by Corning Incorporated), and spin-coated using a spin coater (MS-B100, manufactured by Mikasa) at 1000 rpm for 20 seconds to form a coating layer. The alkali-free glass plate on which the coating layer was formed was heated at 80° C. for 2 minutes. Next, the alkali-free glass plate on which the coating layer was formed was heated at 120° C. for 5 minutes to obtain an alkali-free glass plate on which a cured film was formed. The thickness of the cured film on the alkali-free glass plate was measured using a stylus film thickness gauge (DekTak XT, manufactured by Bruker) and found to be 1.5 μm.

(3-3) Evaluation of Curability Using the obtained cured film, the curability of the composition was evaluated according to the following evaluation criteria. The results are shown in Table 1. The curability was evaluated by immersing an alkali-free glass plate on which a cured film had been 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 film thickness retention before and after immersion (film thickness retention = film thickness after immersion / film thickness before immersion).
A: No change in appearance, film thickness retention rate 90% or more but less than 100% B: No change in appearance, film thickness retention rate 80% or more but less than 90% C: No change in appearance, film thickness retention rate less than 80% D: Regardless of film thickness retention rate, the cured film became cloudy after immersion

(4) Patterning property (4-1) Preparation of cured film for evaluating patterning property (Examples 3 to 6, Comparative Examples 1 to 4)
The composition prepared above was dropped in about 3 cc onto an alkali-free glass plate (Eagle XG, thickness 0.7 mm, manufactured by Corning Incorporated), and spin-coated using a spin coater (MS-B100, manufactured by Mikasa) under conditions of 1000 rpm and 20 seconds to form a coating layer. The alkali-free glass plate on which the coating layer was formed was heated at 80 ° C. for 2 minutes. Next, the alkali-free glass plate on which the coating layer was formed was exposed to proximity exposure through a photomask with a high-pressure mercury lamp proximity UV exposure device (UV-3300SC, manufactured by Ushio) in an air atmosphere with an irradiation energy of 1000 mJ / cm ^2, with a gap of 200 μm provided between the photomask and the coating layer surface. Subsequently, the alkali-free glass plate on which the coating layer was formed after exposure was heated at 80 ° C. for 2 minutes. Next, the glass plate was immersed in a propylene glycol monomethyl ether acetate (PGMEA) solution for 1 minute, and then immersed in pure water for 1 minute to perform development. Subsequently, the substrate was heated on a hot plate at 120° C. for 5 minutes to obtain an alkali-free glass plate on which a patterned cured film was formed. The thickness of the non-patterned portion of the cured film on the alkali-free glass plate was measured with a stylus film thickness meter (DekTak XT, manufactured by Bruker) and found to be 1.5 μm.

(4-2) Evaluation of Patterning Ability The patterning ability of the obtained cured film was evaluated according to the following evaluation criteria. The results are shown in Table 1. The patterning ability was evaluated by observing a cross section of a 5 μm wide, one-to-one line-and-space pattern, and using the top loss rate (= film thickness difference between non-patterned portion and patterned portion ÷ film thickness of non-patterned portion). A smaller top loss rate, i.e., closer to 0%, means better patterning ability.
A: Top loss rate is 0% or more and 10% or less. B: Top loss rate is 10% or more and 20% or less. C: Top loss rate is 20% or more and 40% or less.

Claims (9)

A compound represented by formula (I).

[In formula (I),
R ¹ represents a hydrogen atom or a monovalent substituent.
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 4.
R represents a monovalent substituent, and when there are multiple R, the multiple R may be the same or different. A group represented by the following formula in formula (I):

The compound according to claim 1 , wherein is bonded at the para position relative to the bonding position of L. The compound according to claim 1, wherein A is an oxygen atom. A composition comprising the compound of claim 1. The composition according to claim 4, further comprising a polymerization initiator. The composition of claim 4 further comprising a solvent. A cured product of the compound described in claim 1 or the composition described in any one of claims 4 to 6. A display device comprising the cured product according to claim 7. A solid-state imaging device comprising the cured product according to claim 7.