Composition and cured product thereof, molding, display unit and solid state imaging device

Abstract

To provide a composition capable of imparting a cured product exhibiting a high refractive index, the composition further excellent in film production properties.SOLUTION: A composition includes: a compound (A) having at least one of a thiirane group or a thietane group; a compound (B) having at least one (meth)acryloyl group; and a base catalyst (C). The compound (B) has at least one (meth)acryloyl group, and includes a compound having an urethane bond within a molecule.SELECTED DRAWING: None

Description

Technical Field

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

Background Art

[0002] In the field of optical devices, a high refractive index material is desired. A lens can be obtained from a high refractive index material, and the optical path in the optical device can be controlled by the lens. A lens is used for the purpose of improving the light condensing efficiency on each photoelectric conversion element in a solid-state imaging device, and a lens is also used for the purpose of improving the light extraction efficiency from pixels in a display device. Conventionally, various high refractive index materials have been developed (for example, Patent Document 1).

Prior Art Documents

Patent Documents

[0003]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0004] However, in conventional curable compositions, problems such as unevenness and peeling may occur during film formation depending on the main component, and the film-forming property may not be sufficient in some cases.

[0005] Therefore, the main object of the present invention is to provide a composition that can give a cured product having a high refractive index and further has excellent film-forming properties.

Means for Solving the Problems

[0006] The present invention provides the composition described in [1] to [4], the molded product described in [5], the cured product described in [6], the display device described in [7], and the solid-state imaging device described in [8]. [1] A compound (A) having at least one thiirane group or thietane group, A compound (B) having at least one (meth)acryloyl group, a base catalyst (C), and containing a composition, wherein the compound (B) includes a compound having at least one (meth)acryloyl group and having a urethane bond in the molecule. [2] The composition according to [1], wherein the compound (B) is a compound having at least one (meth)acryloyl group and having no acidic functional group. [3] The composition according to [1] or [2], further containing a polymerization inhibitor (D). [4] The composition according to any one of [1] to [3], wherein the compound (A) is a compound represented by formula (A-1). [Chemical formula] [In formula (A-1), L represents a single bond or a divalent group, and the two Ls may be the same or different. A 1 represents an oxygen atom or a sulfur atom, and the two As 1 may be the same or different. However, at least one of the two As 1 is a sulfur atom. m represents 0 or 1, and the two ms may be the same or different. n represents an integer from 0 to 6. R 1 represents a monovalent substituent, and when there are a plurality of Rs 1 , the plurality of Rs 1 may be the same or different. R 2 represents a hydrogen atom or a monovalent substituent, and the two Rs 2 may be the same or different.] [5] A molded article obtained by curing the composition according to any one of [1] to [4]. [6] A cured product of the composition according to any one of [1] to [4]. [7] A display device including the cured product according to [6]. A solid-state imaging device including a cured product described in [8][6].

Advantages of the Invention

[0007] According to the present invention, it is possible to provide a cured product exhibiting a high refractive index, and a composition excellent in film-forming properties is provided. Some forms of the composition are also excellent in thick film formability, solvent resistance, etc. Further, according to the present invention, a molded product using such a composition, a cured product of such a composition, a display device including the cured product, and a solid-state imaging device including the cured product are provided.

Embodiments for Carrying Out the Invention

[0008] Hereinafter, embodiments of the present invention will be described in detail. However, the present invention is not limited to the following embodiments.

[0009] In this specification, a numerical range indicated by "~" indicates a range including the numerical values described before and after "~" as the minimum value and the maximum value, respectively. In the numerical ranges described stepwise in this specification, the upper limit value or the lower limit value described in one numerical range may be replaced with the upper limit value or the lower limit value of the numerical range described in other stepwise descriptions. Also, in the numerical ranges described in this specification, the upper limit value or the lower limit value of the numerical range may be replaced with the value shown in the examples.

[0010] In this specification, (meth)acrylate means acrylate or the corresponding methacrylate. The same applies to other similar expressions such as (meth)acryloyl group and (meth)acrylic acid ester.

[0011] In this specification, the materials exemplified below may be used alone or in combination of two or more within the range where the conditions are met, unless otherwise specified. The content of each component means the total amount of the plurality of substances corresponding to each component when there are a plurality of substances corresponding to each component, unless otherwise specified.

[0012] <Composition> The composition of one embodiment contains a compound (A) having at least one thiirane group or thietane group (hereinafter, may be referred to as “component (A)”), a compound (B) having at least one (meth)acryloyl group (hereinafter, may be referred to as “component (B)”), and a base catalyst (C) (hereinafter, may be referred to as “component (C)”). According to the composition of this embodiment, it is possible to provide a cured product having a high refractive index. Further, the composition of this embodiment is excellent in film-forming properties. The composition of this embodiment may further contain a polymerization inhibitor (D) or the like.

[0013] Component (A): A compound having at least one thiirane group or thietane group The composition of this embodiment contains component (A). Component (A) can be a curable compound. By the composition containing component (A), it is possible to provide a cured product having a high refractive index by the polymerization of component (A) itself or the polymerization of component (A) and component (B). In this specification, a compound having at least one thiirane group or thietane group and at least one (meth)acryloyl group is included in component (A).

[0014] Component (A) can be used without particular limitation as long as it is a compound having at least one thiirane group or thietane group. Component (A) may be, for example, a compound having at least one group represented by formula (X0), and preferably a compound having at least one group represented by formula (X1).

[0015]

Chemical formula

[0016] In formula (X0), m represents 0 or 1. R 2 represents a hydrogen atom or a monovalent substituent. * represents the bonding position.

[0017]

Chemical formula

[0018] In formula (X1), L represents a single bond or a divalent group. m represents 0 or 1. R 2 represents a hydrogen atom or a monovalent substituent. * represents the bonding position.

[0019] Examples of the divalent group represented by L include a divalent aliphatic chain hydrocarbon group which may have a substituent; a divalent alicyclic hydrocarbon group which may have a substituent; a divalent aromatic hydrocarbon group which may have a substituent; a divalent group composed of a combination of these (for example, an aralkylene group), and other divalent hydrocarbon groups. The methylene group (-CH2-) contained in the divalent group may be substituted with -O-, -S-, -NR A -(R A represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms).), -CO-, or -SO2-.

[0020] Examples of the divalent aliphatic chain hydrocarbon group include saturated or unsaturated aliphatic chain hydrocarbon groups. More specifically, alkane diyl groups such as methylene group, ethylene group, propane diyl group, butane diyl group, pentane diyl group, hexane diyl group, heptane diyl group, octane diyl group, nonane diyl group, decane diyl group, undecane diyl group, dodecane diyl group, tridecane diyl group, tetradecane diyl group, pentadecane diyl group, hexadecane diyl group, heptadecane diyl group, octadecane diyl group, nonadecane diyl group, and eicosane diyl group can be mentioned. The divalent aliphatic chain hydrocarbon group may be linear or branched. The number of carbon atoms of the divalent aliphatic chain hydrocarbon group is usually 1 to 20, preferably 1 to 10, more preferably 1 to 6, still more preferably 1 to 4, and particularly preferably 1 or 2.

[0021] Examples of the substituent that the divalent aliphatic chain hydrocarbon group may have include halogen atoms such as fluorine atom, chlorine atom, bromine atom, and iodine atom; hydroxy group; amino group; acetyl group; cyano group and the like.

[0022] Examples of the divalent alicyclic hydrocarbon group include saturated or unsaturated alicyclic hydrocarbon groups. More specifically, monocyclic alicyclic hydrocarbon groups such as cyclopropanediyl group, cyclobutanediyl group, cyclopentanediyl group, cyclohexanediyl group, cyclooctanediyl group, cyclononanediyl group, cyclodecanediyl group; 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, tricyclo[5.3.1.1]dodecanediyl group and the like. The number of carbon atoms of the divalent alicyclic hydrocarbon group is usually 3 to 20, preferably 3 to 10, more preferably 3 to 6, and still more preferably 5 or 6.

[0023] Examples of the substituent 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 group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group; halogen atoms such as fluorine atom, chlorine atom, bromine atom, iodine atom; hydroxy group; amino group; acetyl group; cyano group and the like.

[0024] The divalent aromatic hydrocarbon group may be monocyclic or polycyclic. Examples of the divalent aromatic hydrocarbon group include phenylene group, naphthylene group, anthracenediyl group, fluorenediyl group and the like. The number of carbon atoms of the divalent aromatic hydrocarbon group is usually 6 to 20, preferably 6 to 10.

[0025] Examples of the substituent that the divalent aromatic hydrocarbon group may have include an alkyl group having 1 to 10 carbon atoms (preferably 1 to 4 carbon atoms) such as methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group; a halogen atom such as fluorine atom, chlorine atom, bromine atom, iodine atom; a hydroxy group; an amino group; an acetyl group; a cyano group and the like.

[0026] R 2 Examples of the monovalent substituent represented by 2 include 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, a monovalent group composed of a combination thereof (for example, an aralkyl group) and other monovalent hydrocarbon groups; a monovalent heterocyclic group which may have a substituent; a hydroxy group; an amino group, a monoalkylamino group having one or two carbon atoms of 1 to 6 such as monomethylamino group, monoethylamino group, dimethylamino group, diethylamino group, methylethylamino group and which may be substituted with an alkyl group; a halogen atom; a nitro group; a cyano group; a carboxy group; a sulfo group; a thiol group; a formyl group; -SF3 group; -SF5 group. The methylene group (-CH2-) contained in the monovalent substituent may be substituted with -O-, -S-, -NR B -(R B represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.). It may be substituted with -CO- or -SO2-. Examples of the group in which the methylene group (-CH2-) contained in the monovalent substituent is substituted with -O- include an alkoxy group having 1 to 12 carbon atoms such as methoxy group, ethoxy group, propoxy group, butoxy group, pentyloxy group, hexyloxy group, heptyloxy group, octyloxy group; an alkoxyalkyl group such as methoxymethyl group, ethoxymethyl group, methoxyethyl group and the like.

[0027] Examples of the monovalent aliphatic chain hydrocarbon group include saturated or unsaturated aliphatic chain hydrocarbon groups. More specifically, alkyl groups such as methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, hexadecyl group, heptadecyl group, octadecyl group, nonadecyl group, eicosyl group, etc. may be mentioned. The monovalent aliphatic chain hydrocarbon group may be linear or branched. The number of carbon atoms of the monovalent aliphatic chain hydrocarbon group is usually 1 to 20, preferably 1 to 10, more preferably 1 to 6, still more preferably 1 to 4, and particularly preferably 1 or 2.

[0028] Examples of the substituent that the monovalent aliphatic chain hydrocarbon group may have include halogen atoms such as fluorine atom, chlorine atom, bromine atom, iodine atom; hydroxy group; amino group; acetyl group; cyano group, etc.

[0029] Examples of the monovalent alicyclic hydrocarbon group include saturated or unsaturated alicyclic hydrocarbon groups. More specifically, monocyclic alicyclic hydrocarbon groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cyclooctyl group, cyclononyl group, cyclodecyl group; 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, tricyclo[5.3.1.1]dodecyl group, etc. may be mentioned. The number of carbon atoms of the monovalent alicyclic hydrocarbon group is usually 3 to 20, preferably 3 to 10, more preferably 3 to 6, still more preferably 5 or 6.

[0030] Examples of the substituent that the monovalent alicyclic hydrocarbon group may have include an alkyl group having 1 to 10 carbon atoms (preferably 1 to 4 carbon atoms) such as methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group; a halogen atom such as fluorine atom, chlorine atom, bromine atom, iodine atom; a hydroxy group; an amino group; an acetyl group; a cyano group and the like.

[0031] The monovalent aromatic hydrocarbon group may be monocyclic or polycyclic. Examples of the monovalent aromatic hydrocarbon group include phenyl group, naphthyl group, anthracenyl group, fluorenyl group and the like. The number of carbon atoms of the monovalent aromatic hydrocarbon group is usually 6 to 20, preferably 6 to 10.

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

[0033] Examples of the monovalent heterocyclic group include an aliphatic heterocyclic group having 4 to 20 carbon atoms or an aromatic heterocyclic group having 3 to 20 carbon atoms such as pyrrolidinyl group, pyrrolinyl group, imidazolidinyl group, imidazolinyl group, oxazolinyl group, thiazolyl group, piperidinyl group, morpholinyl group, piperazinyl group, indolyl group, isoindolyl group, quinolyl group, thienyl group, pyrrolyl group, furyl group and the like.

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

[0035] m represents 0 or 1. When m is 0, it represents a three-membered ring structure which is a thiirane group, and when m is 1, it represents a four-membered ring structure which is a thietane group. m is preferably 0.

[0036] From the viewpoint of the high refractive index of the cured product, the component (A) is preferably a compound containing an aromatic ring. Examples of the aromatic ring include aromatic hydrocarbon rings such as benzene ring, naphthalene ring, and anthracene ring; aromatic heterocyclic rings such as furan ring, pyrrole ring, benzofuran ring, thiophene ring, benzothiophene ring, indole ring, pyridine ring, quinoline ring, isoquinoline ring, pyridazine ring, pyrimidine ring, and triazine ring. The aromatic ring is preferably a benzene ring or a naphthalene ring, more preferably a naphthalene ring.

[0037] From the viewpoint of the high refractive index of the cured product, the component (A) is preferably a compound represented by the formula (A-1) (hereinafter, may be referred to as "compound (A-1)").

[0038]

Chemical formula

[0039] In the formula (A-1), L represents a single bond or a divalent group, and the two Ls may be the same or different. A 1 represents an oxygen atom or a sulfur atom, and the two As 1 may be the same or different. However, at least one of the two As 1 is a sulfur atom. m represents 0 or 1, and the two ms may be the same or different. n represents an integer from 0 to 6. R 1 represents a monovalent substituent, and when there are a plurality of Rs 1 , the plurality of Rs 1 may be the same or different. R 2represents a hydrogen atom or a monovalent substituent, and the two Rs 2 may be the same or different.

[0040] In the compound (A-1), the two groups represented by the formula (X) may be bonded to any position of the 1st to 8th positions of the naphthalene ring. The groups represented by the formula (X) on the naphthalene ring may be bonded to any two positions of, for example, the 1st to 4th positions (5th to 8th positions), or may be bonded to any one position of the 1st to 4th positions (5th to 8th positions) and any one position of the 5th to 8th positions (1st to 4th positions). The groups represented by the formula (X) on the naphthalene ring are preferably bonded to any one position of the 1st to 4th positions (5th to 8th positions) and any one position of the 5th to 8th positions (1st to 4th positions).

[0041] [Chemical formula]

[0042] In the formula (X), L, A 1 , m, and R 2 have the same meanings as described above, and * represents the bonding position.

[0043] When the compound (A-1) has a monovalent substituent represented by one or more Rs 1 , the monovalent substituent represented by R 1 may be bonded to any position of the 1st to 8th positions of the naphthalene ring excluding the bonding position of the group represented by the formula (X).

[0044] L represents a single bond or a divalent group, and the two Ls may be the same or different. In the compound (A-1), the two Ls are preferably such that at least one of them is an alkanediyl group, and more preferably both are alkanediyl groups. In this case, the number of carbon atoms of the alkanediyl group is preferably 1 to 10, more preferably 1 to 6, still more preferably 1 to 4, and particularly preferably 1 or 2.

[0045] A 1 represents an oxygen atom or a sulfur atom, and the two As 1They may be the same or different. However, at least one of the two A's 1 is a sulfur atom. In the compound (A-1), the two A's 1 are preferably both sulfur atoms. As the number of sulfur atoms as A 1 increases, a cured product showing a higher refractive index can be provided, and there is a tendency for better curability.

[0046] m represents 0 or 1, and the two m's may be the same or different. In the compound (A-1), the two m's are preferably both 0.

[0047] n represents any integer from 0 to 6. n is preferably any integer from 0 to 3, more preferably any integer from 0 to 2, still more preferably 0 or 1, and particularly preferably 0.

[0048] R 1 represents a monovalent substituent. When there are a plurality of R's 1 , the plurality of R's 1 may be the same or different. The monovalent substituent represented by R 1 can be exemplified by the same ones as the monovalent substituent represented by R 2 .

[0049] R 2 represents a hydrogen atom or a monovalent substituent, and the two R's 2 may be the same or different. In the compound (A-1), the two R's 2 are preferably a hydrogen atom or a monovalent aliphatic chain hydrocarbon group, more preferably a hydrogen atom or a monovalent aliphatic chain hydrocarbon group having 1 to 6 carbon atoms, still more preferably a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and particularly preferably a hydrogen atom, a methyl group, or an ethyl group.

[0050] As the component (compound (A-1)), for example, compounds represented by formula (Aa), formula (Ab), formula (Ac), formula (Ad), formula (Ae), and formula (Af) can be mentioned. L, A 1 , m, n, R 1 , and R 2 represent the same meaning as described above.

[0051] [Chemical formula]

[0052] In formula (Aa), formula (Ab), formula (Ac), formula (Ad), formula (Ae), and formula (Af), two Ls are preferably such that at least one is an alkanediyl group, more preferably both are alkanediyl groups. In this case, the number of carbon atoms of the alkanediyl group is preferably 1 to 10, more preferably 1 to 6, still more preferably 1 to 4, and particularly preferably 1 or 2.

[0053] In formula (Aa), formula (Ab), formula (Ac), formula (Ad), formula (Ae), and formula (Af), two ms are each independently 0 or 1, preferably 0. In formula (Aa), formula (Ab), formula (Ac), formula (Ad), formula (Ae), and formula (Af), two ms are preferably both 0.

[0054] In formula (Aa), formula (Ab), formula (Ac), formula (Ad), formula (Ae), and formula (Af), n is each independently an integer from 0 to 6, preferably an integer from 0 to 3, more preferably an integer from 0 to 2, still more preferably 0 or 1, and particularly preferably 0.

[0055] In formula (Aa), formula (Ab), formula (Ac), formula (Ad), formula (Ae), and formula (Af), two As 1 are each independently an oxygen atom or a sulfur atom. However, at least one of the two As 1 is a sulfur atom. A1 Preferably, both are sulfur atoms.

[0056] In formula (Aa), formula (Ab), formula (Ac), formula (Ad), formula (Ae), and formula (Af), the two Rs 2 are each independently preferably a hydrogen atom or a monovalent aliphatic chain hydrocarbon group, more preferably a hydrogen atom or a monovalent aliphatic chain hydrocarbon group having 1 to 6 carbon atoms, still more preferably a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and particularly preferably a hydrogen atom, a methyl group, or an ethyl group. The two Rs 2 are preferably the same.

[0057] Specific examples of compound (A-1) are illustrated below, but are not limited thereto.

[0058]

Chemical formula

[0059]

Chemical formula

[0060]

Chemical formula

[0061]

Chemical formula

[0062]

Chemical formula

[0063]

Chemical formula

[0064]

Chemical formula

[0065]

Chem.

[0066]

Chem.

[0067]

Chem.

[0068]

Chem.

[0069]

Chem.

[0070]

Chem.

[0071]

Chem.

[0072]

Chem.

[0073]

Chem.

[0074] The molecular weight of component (A) is preferably 2,000 or less, more preferably 1,000 or less, and still more preferably 750 or less from the viewpoint of synthesis. The molecular weight of component (A) is preferably 50 or more, more preferably 100 or more, and still more preferably 150 or more from the viewpoint of volatility.

[0075] Compound (A-1) as component (A) can be obtained by synthesizing a compound represented by formula (A-1a) (hereinafter sometimes referred to as "compound (A-1a)") and reacting the compound (A-1a) with a sulfurizing agent.

[0076]

Chemical formula

[0077] In formula (A-1a), L, m, n, R 1 , and R 2 represent the same meaning as in the above (formula (A-1)).

[0078] Compound (A-1a) can be obtained, for example, by a method including a step of reacting a compound represented by formula (A-2) (hereinafter sometimes referred to as "compound (A-2)") with a compound represented by formula (A-3) (hereinafter sometimes referred to as "compound (A-3)").

[0079]

Chemical formula

[0080] In formula (A-2), n and R 1 represent the same meaning as above.

[0081]

Chemical formula

[0082] In formula (A-3), L, m, and R 2 represent the same meaning as above, and X represents a leaving group.

[0083] The reaction between compound (A-2) and compound (A-3) can be carried out, for example, in the presence of a base. Examples of the base include inorganic bases such as sodium hydroxide, potassium hydroxide, lithium hydroxide, cesium hydroxide, sodium carbonate, potassium carbonate, lithium carbonate, cesium carbonate, sodium hydride, lithium aluminum hydride, sodium borohydride, sodium bicarbonate, potassium bicarbonate, lithium bicarbonate, cesium bicarbonate; metal alkoxides such as sodium methoxide, potassium methoxide, lithium methoxide, sodium ethoxide, potassium ethoxide, sodium isopropoxide, potassium isopropoxide, sodium t-butoxide, potassium t-butoxide; organic bases such as ammonia, methylamine, dimethylamine, trimethylamine, triethylamine, diisopropylethylamine, triisopropylamine, DBU (1,8-diazabicyclo[5.4.0]undec-7-ene), DABCO (1,4-diazabicyclo[2.2.2]octane), pyridine, 2,6-dimethylpyridine, 2,6-di-t-butylpyridine, dimethylaminopyridine, triphenylphosphine, tetramethylammonium bromide, tetramethylammonium chloride. The amount of the base used may be, for example, 0.0001 to 10 moles, preferably 0.001 to 5 moles, more preferably 0.01 to 4 moles, still more preferably 0.1 to 3 moles, per 1 mole of compound (A-2).

[0084] In addition, two or more types of bases may be used in combination. When used in combination, carbonates such as sodium carbonate, potassium carbonate, lithium carbonate, cesium carbonate, etc., or hydrogen carbonates such as sodium hydrogen carbonate, potassium hydrogen carbonate, lithium hydrogen carbonate, cesium hydrogen carbonate, etc., and metal hydroxides such as sodium hydroxide, potassium hydroxide, lithium hydroxide, cesium hydroxide, etc., or metal alkoxides such as sodium methoxide, potassium methoxide, lithium methoxide, sodium ethoxide, potassium ethoxide, sodium isopropoxide, potassium isopropoxide, sodium t-butoxide, potassium t-butoxide, etc. are preferably used in combination, and a combination of a hydrogen carbonate and a metal hydroxide is more preferable. When used in combination, two types may be added simultaneously or stepwise.

[0085] In the compound (A-3), examples of the leaving group represented by X include halogen atoms such as fluorine atom, chlorine atom, bromine atom, iodine atom; alkylsulfonyl groups such as methylsulfonyl group, ethylsulfonyl group, propylsulfonyl group, butylsulfonyl group, trifluoromethylsulfonyl group, perfluoroethylsulfonyl group, perfluoropropylsulfonyl group, perfluorobutylsulfonyl group; and arylsulfonyl groups such as phenylsulfonyl group, p-toluenesulfonyl group, p-fluorophenylsulfonyl group, pentafluorophenylsulfonyl group, etc. Specific examples of the compound (A-3) include epihalohydrin compounds (compounds in which L is a methylene group, m is 0, R 2 is a hydrogen atom, and X is a halogen atom). The amount of the compound (A-3) to be used may be, for example, 0.01 to 20 moles, preferably 0.5 to 15 moles, per 1 mole of the compound (A-2). In this step, the reaction may be carried out using two or more types of the compound (A-3).

[0086] The reaction between compound (A-2) and compound (A-3) is preferably carried out in a solvent. Examples of the solvent include, in addition to water, organic solvents such as ketones, aromatic hydrocarbons, halogenated aromatic hydrocarbons, aliphatic hydrocarbons, halogenated aliphatic hydrocarbons, ethers, alcohols, glymes, esters, aliphatic nitriles, sulfoxides, amides and the like. The following solvents are exemplified as the organic solvent.

[0087] 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.

[0088] The temperature of the reaction between compound (A-2) and compound (A-3) may be, for example, -80 to 200 °C, preferably -40 to 150 °C, more preferably -20 to 120 °C, and even more preferably -5 to 100 °C.

[0089] In this way, compound (A-1a) can be obtained. When using the compound (A-1a) obtained in the synthesis of compound (A-1), compound (A-1a) may be used after isolation, or may be used as it is without isolation.

[0090] Compound (A-1) can be obtained, for example, by a method including a step of reacting compound (A-1a) with a sulfurizing agent.

[0091] The reaction between compound (A-1a) and a sulfurizing agent is a reaction in which the oxygen atom of the epoxy ring or oxetanyl ring possessed by compound (A-1a) is substituted with a sulfur atom using the sulfurizing agent to form a thiirane ring (episulfide ring) or a thietane ring. Examples of the sulfurizing agent include thiourea, methylthiourea, dimethylthiourea, trimethylthiourea, tetramethylthiourea, tetraethylthiourea, ethylenethiourea, phenylthiourea, diphenylthiourea, tolylthiourea, ditolylthiourea, sodium thiocyanate, potassium thiocyanate, etc. The amount of the sulfurizing agent used can be arbitrarily adjusted according to the oxygen atom to be substituted. The amount of the sulfurizing agent used is, for example, 0.01 to 20 moles, preferably 0.5 to 10 moles, per 1 mole of compound (A-1a). Also, by adjusting the amount of the sulfurizing agent used, the reaction temperature, the reaction time, etc., both oxygen atoms in compound (A-1a) can be replaced with sulfur atoms, or one oxygen atom in compound (A-1a) can be replaced with a sulfur atom.

[0092] The reaction of compound (A-1a) with a sulfurizing agent is preferably carried out in a solvent. Examples of the solvent include the same solvents as those exemplified in the reaction of compound (A-2) and compound (A-3). The reaction of compound (A-1a) with a sulfurizing agent may be, for example, at -80 to 200 °C, preferably -40 to 100 °C, more preferably -20 to 80 °C, and even more preferably -5 to 60 °C.

[0093] A polymerization inhibitor may be added to the reaction system to suppress the polymerization of the produced compound (A-1). Examples of the polymerization inhibitor include acids, acid anhydrides, etc. More specifically, inorganic acidic compounds such as nitric acid, hydrogen chloride (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, phosphoryl chloride, phosphoryl bromide, phosphorus sulfide, phosphorus trichloride, phosphorus tribromide, phosphorus pentachloride, hydrocyanic acid, chromic acid, nitric anhydride, sulfuric anhydride, boron oxide, arsenic pentoxide, phosphorus pentoxide, chromic anhydride, 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, 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 acetate, maleic acid, benzoic acid, phenylacetic acid, o-toluic acid, m-toluic acid, p-toluic acid, salicylic acid, 2-methoxybenzoic acid, 3-methoxybenzoic acid, benzoylbenzoic acid, phthalic acid, isophthalic acid, terephthalic acid, benzylic 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, 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, mono-, di- and trilauryl phosphate, etc., and phosphorous acids in which these phosphate moieties have become phosphite; Organic phosphorus compounds such as dialkyldithiophosphoric acids typified by dimethyldithiophosphoric acid; Phenols such as phenol, catechol, t-butylcatechol, 2,6-di-t-butylcresol, 2,6-di-t-butylethylphenol, resorcinol, hydroquinone, phloroglucin, pyrogallol, cresol, ethylphenol, butylphenol, nonylphenol, hydroxyphenylacetic acid, hydroxyphenylpropionic acid, hydroxyphenylacetamide, 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, 2,4,6-trichlorophenol, etc.; 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, methanylic acid, sulfanilic acid, 4B-acid, diaminostilbenesulfonic acid, biphenylsulfonic acid, α-naphthalenesulfonic acid, β-naphthalenesulfonic acid, perylene acid, Laurent acid, phenyl J-acid, etc. And so on.

[0094] The amount of the polymerization inhibitor used may be, for example, 0.0001 to 1.0 mol, preferably 0.001 to 0.5 mol, more preferably 0.01 to 0.25 mol, and still more preferably 0.05 to 0.15 mol, per 1 mol of the compound (A-1). Among these, the polymerization inhibitor is preferably acetic acid, acetic anhydride, maleic acid, maleic anhydride, phosphoric acid, an alkali metal hydrogen phosphate, or an alkali metal dihydrogen phosphate.

[0095] The stability over time of the compound (A-1) obtained can be improved by washing the product solution after the reaction with an acidic aqueous solution. Specific examples of the acid used in the acidic aqueous solution include the acids exemplified above as the polymerization inhibitor. The acid may be used alone or in a mixture of two or more. The acidic aqueous solution usually tends to exhibit an effect at pH 6 or lower, but a more effective range is pH 3 or lower. The acid used in the acidic aqueous solution is preferably an aqueous solution of hydrogen chloride (hydrochloric acid), sulfuric acid, phosphoric acid, and / or maleic acid.

[0096] Furthermore, a hydrogen sulfide adsorbent can also be used to improve the stability of the compound (A-1). Examples of the hydrogen sulfide adsorbent include iron(III) hydroxide, zinc oxide, KNK-301 (zinc oxide-based adsorbent, manufactured by Kureha Corporation), Nionon 202A (iron oxide-based adsorbent, manufactured by Ibuki Shoji Co., Ltd.), Limonic (iron hydroxide-based, manufactured by Nippon Limnite Co., Ltd.), and the like. The hydrogen sulfide adsorbent may be added during the reaction or used by adding it during the purification after the reaction.

[0097] (A) component content may be, for example, 30 to 98% by mass based on the total amount of the solid content of the composition because the effects of the present invention can be easily obtained sufficiently. The content of the (A) component is preferably 40% by mass or more, more preferably 50% by mass or more, still more preferably 60% by mass or more, preferably 97% by mass or less, more preferably 95% by mass or less, and still more preferably 92% by mass or less, based on the total amount of the composition.

[0098] The total amount of the solid content of the composition means the sum of the components contained in the composition excluding the solvent. The content of each component in the solid content of the composition can be measured by known analytical means such as liquid chromatography and gas chromatography. The content of each component in the solid content of the composition may be calculated from the formulation at the time of composition preparation.

[0099] Component (B): A compound having at least one (meth)acryloyl group The composition of the present embodiment contains component (B). Component (B) includes a compound having at least one (meth)acryloyl group and a urethane bond in the molecule (hereinafter sometimes referred to as “component (B1)”). By combining component (B) (component (B1)) with component (A), it tends to be difficult for defects such as unevenness and peeling to occur during film formation, and it becomes possible to form a good cured film with few defects. Further, by combining component (B) (component (B1)) with component (A), the viscosity of the composition can be improved (the composition can be thickened), and by using the composition, it becomes possible to form a cured film with a thick film (for example, 1.0 μm or more). That is, the composition of the present embodiment is also excellent in terms of thick film formability.

[0100] Component (B) is preferably a compound having at least one (meth)acryloyl group and no acidic functional group from the viewpoint of curability. Here, the acidic functional group means a group capable of releasing a proton (H + ) such as a carboxylic acid group (-COOH), a sulfonic acid group (-SO3H), a phosphoric acid group (-PO4H2), and a boronic acid group (-BO2H2). However, groups having no releasable proton (the releasable proton is substituted with an alkali metal ion or the like), such as a carboxylate group such as -COONa, a sulfonate group such as -SO3Na, a phosphate group such as -PO4Na2, and a borate group such as -BO2Na2, are not included in the acidic functional group.

[0101] (B1) components include, for example, urethane (meth) acrylates having a urethane bond in the molecule. Urethane (meth) acrylates are generally produced by reacting a (meth) acrylate having a hydroxyl group, a polyisocyanate, and a polyol added as necessary.

[0102] Examples of urethane (meth) acrylates include urethane (meth) acrylates having a polyester structure in the molecule and urethane (meth) acrylates having a polyether structure in the molecule. Examples of commercially available urethane (meth) acrylates include the NK Oligo U series, UA series, etc. manufactured by Shin-Nakamura Chemical Co., Ltd.; the SUA series, RUA series, etc. manufactured by Asia Industry Co., Ltd.; the UF series, AH series, etc. manufactured by Kyoeisha Chemical Co., Ltd.; the R series, RST series, GX series, etc. manufactured by Daiichi Kogyo Seiyaku Co., Ltd.

[0103] From the perspective of synthesis, the molecular weight of the (B1) component is preferably 100,000 or less, more preferably 20,000 or less, and even more preferably 10,000 or less. From the perspective of volatility, the (B1) component is preferably 100 or more, more preferably 300 or more, and even more preferably 500 or more.

[0104] Since the effects of the present invention can be easily obtained sufficiently, the content of the (B1) component may be, for example, 30 to 100% by mass based on the total amount of the (B) component. The content of the (B1) component is preferably 50 to 100% by mass, more preferably 70 to 100% by mass, and even more preferably 80 to 100% by mass based on the total amount of the (B) component.

[0105] (Component (B) may contain a compound having at least one (meth)acryloyl group and no urethane bond in the molecule (hereinafter sometimes referred to as “component (B2)”). Examples of component (B2) include monofunctional (meth)acrylate compounds having one (meth)acryloyl group and no urethane bond in the molecule, and polyfunctional (meth)acrylate compounds having two or more (meth)acryloyl groups and no urethane bond in the molecule. The number of (meth)acryloyl groups in the polyfunctional (meth)acrylate compound is preferably 2 to 6, more preferably 2 to 3.

[0106] Examples of monofunctional (meth)acrylate compounds having one (meth)acryloyl group and no urethane bond in the molecule include (meth)acrylic acid; alkyl (meth)acrylates having an alkyl group such as methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, tert-butyl (meth)acrylate, n-pentyl (meth)acrylate, n-hexyl (meth)acrylate, n-octyl (meth)acrylate, isooctyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, isodecyl (meth)acrylate, dodecyl (meth)acrylate (n-lauryl (meth)acrylate), isomyristyl (meth)acrylate, stearyl (meth)acrylate, isostearyl acrylate; alkenyl (meth)acrylates having an alkenyl group such as 3-butenyl (meth)acrylate; (meth)acrylates having an aromatic group such as benzyl (meth)acrylate, phenoxyethyl (meth)acrylate; alkoxypolyalkylene glycol (meth)acrylates such as methoxytetraethylene glycol (meth)acrylate, methoxyhexaethylene glycol (meth)acrylate, methoxyoctaethylene glycol (meth)acrylate, methoxynonaethylene glycol (meth)acrylate, methoxypolyethylene glycol (meth)acrylate, methoxyheptapropylene glycol (meth)acrylate, ethoxytetraethylene glycol (meth)acrylate, butoxyethylene glycol (meth)acrylate, butoxydiethylene glycol (meth)acrylate; (meth)acrylates having an alicyclic group such as cyclohexyl (meth)acrylate, isobornyl (meth)acrylate, dicyclopentanyl (meth)acrylate, and the like.

[0107] Examples of the polyfunctional (meth)acrylate compound having two or more (meth)acryloyl groups and no urethane bond in the molecule include, for example, a (meth)acrylate compound having two (meth)acryloyl groups and no urethane bond in the molecule, a (meth)acrylate compound having three or more (meth)acryloyl groups and no urethane bond in the molecule, and the like.

[0108] Examples of the (meth)acrylate compound having two (meth)acryloyl groups and no urethane bond in the molecule include, for example, 1,3-butanediol di(meth)acrylate, 1,3-butanediol (meth)acrylate, 1,6-hexanediol di(meth)acrylate, ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, polyethylene glycol diacrylate, bis(acryloyloxyethyl) ether of bisphenol A, ethylene oxide-modified bisphenol A di(meth)acrylate, propylene oxide-modified neopentyl glycol di(meth)acrylate, ethylene oxide-modified neopentyl glycol di(meth)acrylate, 3-methylpentanediol di(meth)acrylate, and the like.

[0109] (Meth)acrylate compounds having three or more (meth)acryloyl groups and no urethane bond in the molecule include, for example, trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, tris(2-hydroxyethyl)isocyanurate tri(meth)acrylate, ethylene oxide-modified trimethylolpropane tri(meth)acrylate, propylene oxide-modified trimethylolpropane tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, tripentaerythritol tetra(meth)acrylate, tripentaerythritol penta(meth)acrylate, tripentaerythritol hexa(meth)acrylate, tripentaerythritol hepta(meth)acrylate, tripentaerythritol octa(meth)acrylate, reaction products of pentaerythritol tri(meth)acrylate and acid anhydride, reaction products of dipentaerythritol penta(meth)acrylate and acid anhydride, reaction products of tripentaerythritol hepta(meth)acrylate and acid anhydride, caprolactone-modified trimethylolpropane tri(meth)acrylate, caprolactone-modified pentaerythritol tri(meth)acrylate, caprolactone-modified tris(2-hydroxyethyl)isocyanurate tri(meth)acrylate, caprolactone-modified pentaerythritol tetra(meth)acrylate, caprolactone-modified dipentaerythritol penta(meth)acrylate, caprolactone-modified dipentaerythritol hexa(meth)acrylate, caprolactone-modified tripentaerythritol tetra(meth)acrylate, caprolactone-modified tripentaerythritol penta(meth)acrylate, caprolactone-modified tripentaerythritol hexa(meth)acrylate, caprolactone-modified tripentaerythritol hepta(meth)acrylate, caprolactone-modified tripentaerythritol octa(meth)acrylate, reaction products of caprolactone-modified pentaerythritol tri(meth)acrylate and acid anhydride, reaction products of caprolactone-modified dipentaerythritol penta(meth)acrylate and acid anhydride,Examples include reaction products of caprolactone-modified tripentaerythritol hepta(meth)acrylate and acid anhydrides.

[0110] (B2) component content may be, for example, 0 to 70% by mass based on the total amount of component (B). The content of component (B1) is preferably 0 to 50% by mass, more preferably 0 to 30% by mass, and still more preferably 0 to 20% by mass based on the total amount of component (B).

[0111] (B) component content may be, for example, 1 to 40% by mass based on the total solid content of the composition because the effects of the present invention are easily obtained sufficiently. The content of component (B) is preferably 2% by mass or more, more preferably 3% by mass or more, and still more preferably 5% by mass or more, and preferably 35% by mass or less, more preferably 30% by mass or less, and still more preferably 25% by mass or less based on the total solid content of the composition.

[0112] (C) component: Base catalyst The composition of this embodiment contains component (C). Component (C) is a component that releases a base that initiates anionic polymerization by at least one of active energy ray irradiation and heat as needed. Examples of component (C) include ammonium salts, DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) salts, DBN (1,5-diazabicyclo[4.3.0]non-5-ene) salts, biguanidium salts, aromatic phosphonium salts, aromatic dimethylureas, aliphatic dimethylureas, guanidine salts, phosphazene salts, imidazole salts, etc. These can initiate anionic polymerization by at least one of active energy ray irradiation and heat due to differences in structure. A compound that can release a base that initiates anionic polymerization by active energy ray irradiation is called a photo base generator, and a compound that can release a base that initiates anionic polymerization by heat is called a thermal base generator.

[0113] (C) component preferably contains a DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) salt from the perspective of solvent resistance in one embodiment. (C) component preferably contains at least one selected from the group consisting of guanidine salts and phosphazene salts from the perspectives of storage stability of the composition and curability and heat resistance of the cured product in one embodiment.

[0114] Examples of the anion constituting the salt include inorganic anions and organic anions. Examples of the anion include hydroxide ion; halide ions such as chloride ion, bromide ion, and iodide ion; carbonate ion; bicarbonate ion; nitrate ion; sulfate ion; sulfite ion; chromate ion; dichromate ion; phosphate ion; cyanide ion; permanganate ion; complex ions such as hexacyanoferrate(III) ion; and organic carboxylic acid ions such as formate ion, acetate ion, propionate ion, butyrate ion, and valerate ion. The anion is preferably an organic carboxylic acid ion from the perspectives of curability, heat resistance, light resistance, and storage stability. The number of carbon atoms constituting the organic carboxylic acid ion is preferably 1 to 20, more preferably 1 to 10.

[0115] The content of (C) component is preferably 0.1 part by mass or more, more preferably 0.5 part by mass or more, from the perspective of enhancing curability and / or heat resistance with respect to 100 parts by mass of the total amount of (A) component, and is preferably 10 parts by mass or less, more preferably 8 parts by mass or less, from the perspective of improving physical properties such as mechanical properties of the cured product.

[0116] (D) component: polymerization inhibitor The composition may contain one or more component (D). Whether to include a polymerization inhibitor in the composition is preferably determined, for example, in consideration of the type of component (A). Component (D) is preferably one that is dissolved or dispersed in a solvent. Component (D) contained in the composition may be added during the preparation of the composition, or may be added after the production of component (A). By containing component (D) in the composition, unintended polymerization of component (A) is suppressed, so that the storage stability of the composition can be improved.

[0117] (D) component can be exemplified by the same ones as the polymerization inhibitors added to the reaction system to suppress the polymerization of the produced compound (A-1). Component (D) is preferably organic carboxylic acids, more preferably organic carboxylic acids having 10 or fewer carbon atoms, still more preferably formic acid or acetic acid.

[0118] When the composition contains component (D), the content of component (D) is preferably 0.01 part by mass or more, more preferably 0.1 part by mass or more, still more preferably 0.5 part by mass or more, particularly preferably 1 part by mass or more, preferably 100 parts by mass or less, more preferably 50 parts by mass or less, still more preferably 25 parts by mass or less, particularly preferably 10 parts by mass or less, based on 100 parts by mass of the total amount of component (A), from the viewpoint of improving the storage stability of the composition.

[0119] Examples of other components contained in the composition include resins, curable compounds other than component (A) and component (B), solvents, additives, etc. Examples of additives include inorganic particles, fillers, polymerization initiation aids, sensitizers, leveling agents, stabilizers, surfactants, antistatic agents, lubricants, antifouling agents, ultraviolet absorbers, antioxidants, dispersants, etc.

[0120] (Resin) The composition may contain one or more resins. By containing a resin in the composition, it is possible to impart developability to the cured product of the composition, or to adjust the mechanical properties and / or optical properties of the cured product and the molded article containing the same. Examples of the resin include, for example, thermoplastic resins and curable resins. The curable resin may be a photocurable resin that cures upon irradiation with active energy rays, or a thermosetting resin that cures upon heating.

[0121] Examples of the thermoplastic resin include, for example, olefin resins such as polyethylene resin, polypropylene resin, and polycycloolefin resin; (meth)acrylic resins such as poly(meth)acrylate resin; styrene resins such as polystyrene resin, styrene-acrylonitrile resin, and acrylonitrile-butadiene-styrene resin; vinyl resins such as polyvinyl chloride resin, 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.

[0122] Examples of the curable resin include resins having a photopolymerizable group or a thermopolymerizable group. More specifically, for example, (meth)acrylic resins, epoxy resins, melamine resins, unsaturated polyester resins, phenol resins, urea resins, alkyd resins, polyimide resins, etc. are mentioned.

[0123] Another example of the resin includes an alkali-soluble resin. By containing an alkali-soluble resin in the composition, developability can be imparted to the cured product of the composition. The alkali-soluble resin means a resin soluble in an aqueous alkali solution. Specifically, for example, resins having a carboxy group and / or a phenolic hydroxyl group are mentioned.

[0124] From the viewpoint of enhancing 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 still more 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 using an aqueous potassium hydroxide solution.

[0125] Also, as another example of the resin, a high refractive index resin can be mentioned. The high refractive index resin means a resin having a refractive index of 1.60 or more at a wavelength of 550 nm.

[0126] The weight average molecular weight (Mw) in terms of standard polystyrene measured by gel permeation chromatography (GPC) of the resin may be, for example, 500 to 2,000,000, preferably 1,000 to 1,000,000, 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, charging method, reaction temperature, and time.

[0127] When the composition contains a resin, the content of the resin is preferably 5% by mass or more, more preferably 10% by mass or more, preferably 80% by mass or less, and more preferably 70% by mass or less based on the total amount of the solid content of the composition.

[0128] (Curing compound other than component (A) and component (B)) The composition may contain one or more curing compounds other than component (A) and component (B). By containing a curing compound other than component (A) and component (B) in the composition, the viscosity or curability of the composition can be adjusted, and the mechanical properties and / or optical properties of the resulting cured product and the molded product containing the same can be adjusted.

[0129] Examples of the curable compound other than the component (A) and the component (B) include, for example, an epoxy compound other than the component (A), an oxetane compound other than the component (A), a hydroxy compound, a vinyl ether compound, an allyl compound, a thiol compound, a polyphenol compound, an iso(thio)cyanate compound, an acid anhydride, and the like.

[0130] When the composition contains a curable compound other than the component (A) and the component (B), the content of the curable compound other than the component (A) and the component (B) is preferably 1% by mass or more, more preferably 2% by mass or more, based on the total amount of the solid content of the composition, and is preferably 30% by mass or less, more preferably 20% by mass or less.

[0131] (Solvent) The composition may contain one or more solvents. The solvent is preferably one that can dissolve or disperse the component (A), and more preferably one that can further dissolve or disperse other components other than the component (A). Examples of the solvent include, for example, the solvents (organic solvents) exemplified in the reaction of the compound (A-2) and the compound (A-3), ester solvents (solvents containing -COO- in the molecule and not containing -O-), ether solvents (solvents containing -O- in the molecule and not containing -COO-), ether ester solvents (solvents containing -COO- and -O- in the molecule), ketone solvents (solvents containing -CO- in the molecule and not containing -COO-), alcohol solvents (solvents containing OH in the molecule and not containing -O-, -CO-, and -COO-), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfoxide, and the like.

[0132] Examples of the ester solvent include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutyrate, ethyl acetate, n-butyl acetate, isobutyl acetate, pentyl formate, isopentyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexanol acetate, γ-butyrolactone, and the like.

[0133] Examples of ether solvents include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenetole, methyl anisole, and the like.

[0134] Examples of ether ester solvents include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, ethyl 2-ethoxy-2-methylpropionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, and the like.

[0135] Examples of the ketone solvent include 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone, isophorone, and the like.

[0136] Examples of the alcohol solvent include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, glycerin, and the like.

[0137] Examples of the aromatic hydrocarbon solvent include benzene, toluene, xylene, mesitylene, and the like.

[0138] Examples of the amide solvent include N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, and the like.

[0139] When the composition contains a solvent, the content of the solvent is preferably 60 parts by mass or more, more preferably 80 parts by mass or more, and preferably 1000 parts by mass or less, more preferably 500 parts by mass or less, based on 100 parts by mass of the total amount 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.

[0140] <Cured Product and Molded Product> The cured product of one embodiment is the cured product of the composition. The molded product of one embodiment is obtained by curing the composition and includes the cured product of the composition. Since the composition is excellent in film-forming property, curability, etc., it 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 component (A), component (B), etc. in 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) shape, plate shape, lens shape, powder shape, granular shape, non-spherical particle shape, crushed particle shape, porous shape, massive continuous body, fibrous shape, tubular shape, hollow fiber shape, etc., and may be any shape according to the use of the molded product, etc.

[0141] The method for obtaining a molded article from the composition is not particularly limited, and examples thereof include a method of forming a film on a substrate and then performing molding by etching or the like, an injection molding method, a casting polymerization molding method, and the like.

[0142] In the casting polymerization molding method, for example, the composition is injected into a molding mold, defoaming or the like is performed as necessary, then it is cured by heating in an oven or the like, and the obtained molded article is taken out. The taken-out molded article can be further irradiated with active energy rays to perform additional curing.

[0143] When forming a film as a molded article on a substrate, the composition is applied to the substrate, dried as necessary to form a coating film (coating layer), and the coating film (coating layer) is cured to obtain a cured film (cured layer) as the molded article. The molded article may be a patterned cured film (cured layer). The patterned cured film can be obtained by patterning by methods such as photolithography, inkjet method, printing method, etc. The patterning method may be, for example, a photolithography method. The photolithography method is a method of applying the composition to a substrate, drying as necessary to form a coating film (coating layer), exposing the coating film (coating layer) through a photomask, and developing the exposed coating film (coating layer).

[0144] Examples of the substrate include glass plates such as quartz glass, borosilicate glass, aluminosilicate glass, soda-lime glass with a silica-coated surface, and non-alkali glass; resin plates such as polycarbonate, polymethyl methacrylate, and polyethylene terephthalate; silicon; substrates with aluminum, silver, silver / copper / palladium alloy thin films or the like formed on these substrates, and the like. Examples of the method for applying the composition to the substrate include spin coating method, slit coating method, slit and spin coating method, and the like.

[0145] 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 the light with wavelengths in these ranges, light near 436 nm, near 408 nm, or near 365 nm may be selectively extracted by a band-pass filter according to the absorption wavelength of the photoinitiator. Specific examples of the light source include a mercury lamp, a light-emitting diode, a metal halide lamp, a halogen lamp, etc. After pattern exposure, the coated film (coating layer) after exposure may be heated (pre-development bake) before development.

[0146] Examples of the developer used for development include an aqueous solution, a solvent, etc. containing an alkaline compound such as potassium hydroxide, sodium hydrogen carbonate, sodium carbonate, tetramethylammonium hydroxide, etc. As the solvent, for example, the solvents (organic solvents) exemplified in the reaction of compound (A-2) and compound (A-3) or the above solvents can be used. The developer may contain a surfactant. Examples of the development method include the paddle method, the dipping method, the spray method, etc. Further heating (post-bake) may be performed on the patterned cured film (cured layer) obtained by development.

[0147] Since the cured product or the molded product containing it is formed from the composition, it can exhibit a high refractive index, and their refractive indices can be controlled to a desired refractive index by adjusting the composition of the composition, etc. The refractive index of the cured product or the molded product containing it at a wavelength of 550 nm may be 1.65 or more, 1.68 or more, 1.70 or more, 1.72 or more, or 1.73 or more. The refractive index of the cured product or the molded product containing it at a wavelength of 550 nm may be, for example, 2.00 or less, or 1.90 or less.

[0148] The refractive index of the cured product or the molded product containing the same at a wavelength of 550 nm can be measured, for example, by the following method. First, a coating film is formed on a substrate, the coating film is cured, and a substrate with a cured film formed thereon is obtained. Next, for the substrate with the cured film formed thereon, a visible ultraviolet spectrophotometer (for example, "V-650" manufactured by JASCO Corporation) equipped with an integrating sphere unit (for example, "ISV-922" manufactured by JASCO Corporation) is used to measure the transmission spectrum and reflection spectrum at wavelengths from 300 nm to 800 nm. Then, among the true reflection spectra obtained by subtracting and smoothing the increase and decrease due to the interference of the reflection spectrum from the transmission spectrum and the reflection spectrum, based on the Fresnel formula (for example, the original text of Hekt Optical I, 5th edition, Maruzen Publishing, 2018, p. 209-226), the refractive index of the cured product or the molded product containing the same at a wavelength of 550 nm is calculated from the value at a wavelength of 550 nm and the refractive index of the substrate. Thereby, the refractive index of the cured product or the molded product containing the same at a wavelength of 550 nm can be obtained.

[0149] <Usage> Examples of the uses of the cured or molded product include, for example, glass substitutes and their surface coating materials; coating materials for window glass, daylighting glass, and light source protection glass for houses, facilities, transportation equipment, etc.; window films for houses, facilities, transportation equipment, etc.; interior and exterior finishing materials, interior and exterior paints, and paint films formed by such paints for houses, facilities, transportation equipment, etc.; alkyd resin lacquer paints and paint films formed by such paints; acrylic lacquer paints and paint films formed by such paints; members for light sources that emit ultraviolet rays such as fluorescent lamps and mercury lamps; shielding materials for electromagnetic waves generated from precision machinery, electronic and electrical equipment members, various displays, etc.; containers or packaging materials for foods, chemicals, pharmaceuticals, etc.; bottles, boxes, blisters, cups, for special packaging, compact disc coats, industrial and agricultural sheets or film materials; fading inhibitors for printed matter, dyed products, dyes and pigments, etc.; protective films for polymer supports (for example, for plastic parts of machinery and automobile parts); printed matter overcoats; inkjet medium coatings; laminated matte finishes; optical light films; safety glass / windshield intermediate layers; electrochromic / photochromic applications; overlaminate films; solar heat control films; cosmetics such as sunscreen creams, shampoos, rinses, hair styling products, etc.; clothing fibers and fabrics for sportswear, stockings, hats, etc.; household interior products such as curtains, carpets, wallpapers, etc.; medical instruments such as plastic lenses, contact lenses, artificial eyes, etc.; optical supplies such as optical filters, backlight display films, prisms, lenses (for example, spectacle lenses, camera lenses, and microlenses, pickup lenses, etc. described later), mirrors, photographic materials, etc.; stationery such as mold films, transfer stickers, anti-graffiti films, tapes, inks, etc.; signboards, indicators, etc. and their surface coating materials; substrates used in optical devices, etc.; optical waveguides; holograms; LED encapsulants, etc.

[0150] The formed article is suitably used as a lens which is an optical article used in an optical device. Examples of the optical device include a solid-state imaging device, a display device, and the like. In a solid-state imaging device, a lens for the purpose of improving the light condensing efficiency to each photoelectric conversion element is used. Further, in a display device, a lens for the purpose of improving the light extraction efficiency from pixels is used. The lens may be a microlens. Examples of the display device include a liquid crystal display device, an organic EL display device, and the like.

[0151] As high refractive index materials, inorganic compounds such as zirconium oxide and titanium oxide have been conventionally known. However, when producing a formed article containing a high refractive index material made of an inorganic compound, molding may not be easy, such as difficulty in the progress of etching, and there may be a problem of contamination due to scattering of the high refractive index material during molding. Such problems can be solved by using the high refractive material of the present embodiment which is an organic compound.

[0152] The cured product of the composition of the present embodiment can be suitably used as a main-chain scission type positive resist. In the formation of a resist pattern using the cured product of the composition of the present embodiment, by irradiation with ionizing radiation or the like (for example, electron beam, KrF laser, ArF laser, EUV laser, etc.), the main chain of the polymer such as component (A), component (B), etc. constituting the cured product is cleaved at the irradiated portion of the resist film and the molecular weight is reduced. Therefore, a difference in solubility in the developer occurs between the exposed portion and the unexposed portion, and a resist pattern is formed. The resist pattern using the cured product of the composition of the present embodiment can be applied when forming a resist pattern in the manufacture of printed circuit boards such as build-up substrates; semiconductors; photomasks; molds, and the like.

Examples

[0153] Hereinafter, the present invention will be described more specifically with reference to examples. However, the present invention is not limited to these examples. In the following, unless otherwise specified, "part" means "part by mass".

[0154] [Synthesis Example 1] <Synthesis of Compound (Aa-1)> ·Synthesis of Compound (Aa-1a)

Chemical formula

[0155] The inside of a four-necked flask equipped with a Dimroth condenser and a thermometer was made into a nitrogen atmosphere, and 30 parts of 1,6-naphthalenedithiol, 165 parts of acetone, 45 parts of pure water, and 139 parts of epichlorohydrin were added to the flask and stirred in an ice bath for 15 minutes. Subsequently, 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 dropped into the above four-necked flask over 1 hour. After the dropping, the temperature was raised to 30 °C and stirred at 30 °C for 2 hours. The obtained mixture was purified to obtain 46 parts of a compound represented by the formula (Aa-1a) (Compound (Aa-1a)).

[0156] 1 H-NMR analysis and LC-MS measurement were performed to confirm the formation of Compound (Aa-1a). 1 H-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

[0157] ·Synthesis of Compound (Aa-1)

Chemical formula

[0158] The inside of a four-necked flask equipped with a Dimroth condenser and a thermometer was made into a nitrogen atmosphere, and 3 parts of Compound (Aa-1a), 30 parts of methanol, 30 parts of toluene, 0.05 part of acetic anhydride, and 3.8 parts of thiourea were added to the flask and stirred at room temperature for 24 hours. The obtained mixture was purified to obtain 2.5 parts of a compound represented by the formula (Aa-1) (Compound (Aa-1)).

[0159] 1 H-NMR analysis and LC-MS measurement were performed, and it was confirmed that the compound (Aa-1) was produced. 1 H-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

[0160] [Examples 1 - 8 and Comparative Examples 1, 2] [Preparation of Compositions] The compounding ingredients shown in Table 1 were placed in a flask in the addition amounts (unit: part) shown in Table 1, and stirred to prepare the liquid compositions of Examples 1 - 8 and Comparative Examples 1, 2. The compositions of Examples 1 - 8 and Comparative Examples 1, 2 were visually transparent, and it was confirmed that the compounding ingredients were uniformly dissolved.

[0161] The details of the abbreviations of the compounding ingredients shown in Table 1 are as follows. Component (A): Compound (A) having at least one thiirane group or thietane group · (A-1): Compound (Aa-1) synthesized in Synthesis Example 1 Component (B): Compound (B) having at least one (meth)acryloyl group Component (B1): Compound having at least one (meth)acryloyl group and having a urethane bond in the molecule · (B1-1): Urethane acrylate (manufactured by Shin-Nakamura Chemical Co., Ltd., "NK Oligo UA-122P", polyester-based, number of functional groups: 2, molecular weight: 1100) · (B1-2): Urethane acrylate (manufactured by Shin-Nakamura Chemical Co., Ltd., "NK Oligo UA-160TM", polyether-based, number of functional groups: 2, molecular weight: 1600) ·(B1-3): Urethane acrylate (manufactured by Asia Industrial Co., Ltd., "SUA-023", polyether type, number of functional groups: 2) ·(B1-4): Urethane acrylate (manufactured by Asia Industrial Co., Ltd., "RUA-049X", number of functional groups: 3) ·(B1-5): Urethane acrylate (manufactured by Kyoeisha Chemical Co., Ltd., "UF-8001G", number of functional groups: 2, molecular weight: 4500) ·(B1-6): Urethane acrylate (manufactured by Kyoeisha Chemical Co., Ltd., "AH-600") ·(B1-7): Urethane acrylate (manufactured by Daiichi Kogyo Seiyaku Co., Ltd., "R-1204B-H") (B2) component: A compound having at least one (meth)acryloyl group and no urethane bond in the molecule ·(B2-1): Acrylate without urethane bond (manufactured by Shin-Nakamura Chemical Co., Ltd., "NK Ester A-9550") (C) component: Base catalyst (C) ·(C-1): DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) salt type thermal anionic polymerization initiator (manufactured by San-Apro Ltd., "U-CAT SA102") (D) component: Polymerization inhibitor (D) ·(D-1): Formic acid Solvent ·(E-1): PGMEA (propylene glycol monomethyl ether acetate)

[0162] <Evaluation test> (1) Film-forming property The compositions of Examples 1 to 8 and Comparative Examples 1 and 2 were each dropped by about 3 mL onto an alkali-free glass plate (thickness 0.7 mm, manufactured by Corning Inc., "Eagle XG"), and spin-coated using a spin coater (manufactured by Mikasa Co., Ltd., "MS-B100") under the conditions of 1000 rpm and 20 seconds to form a coating film. The alkali-free glass plate with the coating film formed was heated at 60 °C for 2 minutes to remove the solvent.

[0163] The obtained coating film was observed, and the film-forming property of the composition was evaluated according to the following evaluation criteria. In the evaluation of the film-forming property, it was evaluated whether or not hole defects occurred. Note that the hole defect means a state in which a hole-shaped non-alkali glass plate exposure part with a diameter of 1 mm or more occurred in the coating film. The peeling defect means a state in which although no non-alkali glass plate exposure part was observed, the film thickness was partially thinned mainly around environmental foreign matters, and crater-shaped defects with a diameter of less than 1 mm occurred. The results are shown in Table 2. A: Neither hole defects nor peeling defects occurred. B: No hole defects occurred, but peeling defects occurred. D: Both hole defects and peeling defects occurred.

[0164] (2) Formation of cured film About 3 mL of the compositions of Examples 1 to 8 and Comparative Examples 1 and 2 were each dropped onto a non-alkali glass plate (thickness 0.7 mm, manufactured by Corning, "Eagle XG"), and spin-coated using a spin coater (manufactured by Mikasa Co., Ltd., "MS-B100") under the conditions of 1000 rpm and 20 seconds to form a coating film. The non-alkali glass plate on which the coating film was formed was heated at 60 °C for 2 minutes to remove the solvent. Next, the non-alkali glass plate on which the coating film was formed was exposed in an air atmosphere using a high-pressure mercury lamp proximity UV exposure apparatus (manufactured by Ushio Inc., "UV-3300SC") with an irradiation energy of 1000 mJ / cm 2 . Subsequently, the non-alkali glass plate on which the coating film was formed after exposure was post-baked and heated at 120 °C for 5 minutes to obtain a non-alkali glass plate on which a cured film was formed.

[0165] (3) Measurement of refractive index Regarding the alkali-free glass plate with a cured film formed in the above (2), a visible ultraviolet spectrophotometer (manufactured by JASCO Corporation, "V-650") equipped with an integrating sphere unit (manufactured by JASCO Corporation, "ISV-922") was used to measure the transmittance spectrum and reflectance spectrum in the wavelength range from 300 nm to 800 nm. Among the true reflectance spectra obtained by subtracting and smoothing the increase and decrease due to the interference of the reflectance spectrum from the transmittance spectrum and reflectance spectrum, the refractive index of the cured film at a wavelength of 550 nm was calculated based on Fresnel's formula (Original of Hector Optics I, 5th Edition, Maruzen Publishing, 2018, p. 209-226) from the value at a wavelength of 550 nm and the refractive index of the alkali-free glass plate (manufactured by Corning, "Eagle XG"). The results are shown in Table 2.

[0166] (4) Thick film formability The film thickness of the cured film obtained in the above (2) was measured, and the thick film formability of the composition was evaluated according to the following evaluation criteria. The film thickness was measured with a stylus profilometer (manufactured by Bruker, "DekTak XT") for the cured film on the alkali-free glass plate. When the cured film obtained in Comparative Example 1 was measured, it was 1.5 μm. A: The film thickness was 1.65 μm or more. B: The film thickness was 1.45 μm or more and less than 1.65 μm. D: The film thickness was less than 1.45 μm.

[0167] (5) Solvent resistance (film thickness retention rate) Using the alkali-free glass plate with a cured film formed in the above (2), the solvent resistance (film thickness retention rate) of the composition was evaluated according to the following evaluation criteria. The solvent resistance was evaluated by immersing the alkali-free glass plate with a cured film formed in acetone at 23 °C for 10 minutes, observing the change in the appearance of the cured film before and after immersion, and calculating the film thickness retention rate before and after immersion (film thickness retention rate = film thickness of the cured film after immersion / film thickness of the cured film before immersion). The results are shown in Table 2. A: There was no change in appearance, and the film thickness retention rate was 100% or less and 90% or more. B: There was no change in appearance, and the film thickness retention rate was less than 90% and 80% or more. D: There was no change in appearance, and the film thickness retention rate was less than 80%.

[0168]

Table 1

[0169]

Table 2

[0170] As shown in Table 2, the compositions of the examples were superior to those of the comparative examples in terms of film-forming properties and refractive index. Also, the compositions of the examples were excellent in thick film-forming properties, solvent resistance, etc. From these results, it was confirmed that the composition of the present invention can give a cured product having a high refractive index and is further excellent in film-forming properties.

Claims

1. A compound (A) having at least one thiirane group or thietane group, A compound (B) having at least one (meth)acryloyl group, A base catalyst (C), Containing, The composition, wherein the compound (B) includes a compound having at least one (meth)acryloyl group and having a urethane bond in the molecule.

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

3. The composition according to claim 1, further containing a polymerization inhibitor (D).

4. The composition according to claim 1, wherein the compound (A) is a compound represented by the formula (A-1). 【Chemical 1】 [In the formula (A-1), L represents a single bond or a divalent group, and the two Ls may be the same or different. A １ represents an oxygen atom or a sulfur atom, and the two A's １ may be the same or different. However, at least one of the two A's １ is a sulfur atom. m represents 0 or 1, and the two ms may be the same or different. n represents an integer of any one of 0 to 6. R １ represents a monovalent substituent, and when there are a plurality of R １ , the plurality of R １ may be the same or different. R ２ represents a hydrogen atom or a monovalent substituent, and the two Rs ２ may be the same or different.]

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

6. A cured product of the composition according to any one of claims 1 to 4.

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

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

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